EPA-600/1-78-031
May 1978
Environmental Health Effects Research Series
IDENTIFICATION OF TOXIC IMPURITIES
IN TECHNICAL GRADES OF PESTICIDES
DESIGNATED AS SUBSTITUTE CHEMICALS
tealth Effects Research Laboratory
Office of Research and Development
U.S. Environmental Protection Agency
Research Triangle Park, North Carolina 27711
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RESEARCH REPORTING SERIES
Research reports of the Office of Research and Development, U.S. Environ-
mental Protection Agency, have been grouped into five series. These five broad
categories were established to facilitate further development and application
of environmental technology. Elimination of traditional grouping was con-
sciously planned to foster technology transfer and a maximum interface in
related fields. The five series are:
1. Environmental Health Effects Research
2. Environmental Protection Technology
3. Ecological Research
4. Environmental Monitoring
5. Socioeconomic Environmental Studies
This report has been assigned to the ENVIRONMENTAL HEALTH EFFECTS
RESEARCH series. This series describes projects and studies relating to the
tolerances of man for unhealthful substances or conditions. This work is gener-
ally assessed from a medical viewpoint, including physiological or psycho-
logical studies. In addition to toxicology and other medical specialities, study
areas include biomedical instrumentation and health research techniques uti-
lizing animals—but always with intended application to human health measures.
This document is available to the public through the National Technical Informa-
tion Service, Springfield, Virginia 22161.
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EPA-600/1-78-031
May 1978
IDENTIFICATION OF TOXIC IMPURITIES IN
TECHNICAL GRADES OF PESTICIDES DESIGNATED
AS SUBSTITUTE CHEMICALS
by
J. S. Warner, A. E. Bearse, R. E. Wyant, and
P. A. Clarke
Battelle Columbus Laboratories
505 King Avenue
Columbus, Ohio 43201
Contract No. 68-02-1705
Project Officer
Ronald L. Baron
Health Effects Research Laboratory
U.S. Environmental Protection Agency
Research Triangle Park, North Carolina 27711
HEALTH EFFECTS RESEARCH LABORATORY
OFFICE OF RESEARCH AND DEVELOPMENT
U.S. ENVIRONMENTAL PROTECTION AGENCY
RESEARCH TRIANGLE PARK, N.C. 27711
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DISCLAIMER
This report has been reviewed by the Health Effects Research
Laboratory, U.S. Environmental Protection Agency, and approved for
publication. Approval does not signify that the contents necessarily
reflect the views and policies of the U.S. Environmental Protection
Agency, nor does mention of trade names or commercial products con-
stitute endorsement or recommendation for use.
ii
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FOREWORD
The many benefits of our modern, developing, industrial society are
accompanied by certain hazards. Careful assessment of the relative risk
of existing and new man-made environmental hazards is necessary for the
establishment of sound regulatory policy. These regulations serve to
enhance the quality of our environment in order to promote the public
health and welfare and the productive capacity of our Nation's population.
The Health Effects Research Laboratory, Research Triangle Park,
conducts a coordinated environmental health research program in toxicology,
epidemiology, and clinical studies using human volunteer subjects.
These studies address problems in air pollution, non-ionizing radiation,
environmental carcinogenesis and the toxicology of pesticides as well as
other chemical pollutants. The Laboratory develops and revises air
quality criteria documents on pollutants for which national ambient air
quality standards exist or are proposed, provides the data for registration
of new pesticides or proposed suspension of those already in use, conducts
research on hazardous and toxic materials, and is preparing the health
basis for non-ionizing radiation standards. Direct support to the
regulatory function of the Agency is provided in the form of expert
testimony and preparation of affidavits as well as expert advice to the
Administrator to assure the adequacy of health care and surveillance of
persons having suffered imminent and substantial endangerment of their
health.
This study was done to identify impurities in technical grade
pesticides. This was accomplished through an evaluation of theoretical
products based upon the mode of manufacture and an actual examination of
selected materials for the presence of toxic impurities.
F. Gordon Hueter, Ph. D.
Acting Director
Health Effects Research Laboratory
iii
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ABSTRACT
Two different approaches were used to Identify potentially harmful
impurities present in technical grade pesticides. One approach was a
theoretical approach that involved a literature search, study the manu-
facturing processes, identifying the main reactions and the numerous side
reactions that may occur, listing the potential impurities that may result,
and estimating the likelihood of the occurrence of such impurities at
yg/g or lower levels in the final product. The second approach was an
experimental approach that involved the use of combined gas chromatography-
mass spectrometry (GC-MS) to identify and quantify the major impurities
actually present in technical-grade materials.
In addition to the above two tasks the program also included maintain-
ing and assaying a repository of selected technical-grade pesticides. At
the request of the Project Officer the task of assaying product purity by
gas chromatography was substituted for the task of identifying and quantifying
impurities by combined GC-MS during the second half of the program.
Thirty-four technical-grade pesticides were included in the repository
and stored at -20 °C in most cases. Samples were shipped to 15 different
EPA or contractor laboratories whenever requested. By having a single lot
of each pesticide stored under conditions that would prevent any significant
decomposition, each laboratory studying a given pesticide would be supplied
identical material and thus permit more meaningful intercorrelation of data
generated.
The theoretical evaluations showed that many dozens or even hundreds
of specific compounds may be present as impurities in technical-grade
pesticides at levels above 1 vg/g. The potential hazard of these possible
contaminants can only be speculated upon based on known toxicants of similar
chemical structure as a basis. Many of the phosphorus-containing Impurities
possibly present in organophosphate pesticides nay be highly toxic as is
known to be the case for paraoxon and tetraethylpyrophosphate. N,N-Diiso-
propylnitrosamine is a potentially highly carcinogenic compound that is a
potential contaminant in trifluralin. Analogs of tetrachlorodibenzodioxin,
one of the most toxic mutagenic chemicals known, can theoretically be formed
during the preparation of parathion, methyl parathion, PCNB, dicamba, and
chlorpyrifos.
iv
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I
Gas chromatographic studies showed that as many as 25 impurities may
be detected at levels above 100 yg/g in some technical-grade pesticides.
Many of the components were identified by GC-MS in technical-grade chlorpyrifos,
dicamba, folpet, malathion, ethyl parathion, parathion, PCNB, phorate, and
trifluralin. The identified components were ones that were predicted to be
present on the basis of the theoretical studies in nearly every case.
The limited data generated on the program has indicated that extensive
additional work is needed to assess the potential hazards of impurities
present in technical-grade pesticides. In the interest of more efficient use
of research funds for this work we have recommended that the following
approaches be included in future efforts:
1. Use high-pressure liquid chromatography (HPLC) and glass
capillary column GC-MS in analytical studies.
2. Look for specific toxic components as predicted by
theoretical evaluations, e.g. dioxins in chlorpyifos,
dicamba, and parathion and diisopropylnitrosamine
in trifluralin.
3. Use in vitro bioassay methods in conjunction with
HPLC fractionation to assess which impurity
fractions are potentially hazardous and should
be characterized more extensively. This approach
should be applied to samples stored under adverse
conditions as well as to fresh technical-grade
material.
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CONTENTS
Abstract iv
Figures viii
Tables ix
1. Introduction 1
2. Conclusions and Recommendations 2
3. Pesticide Repository 5
4. Theoretical Evaluations 7
5. Analytical Studies 8
GC Determination of Impurities 8
GC-MS Determination of Impurities 8
Appendices
A. Literature References
Aldicarb 23
Aspon 26
Azinphosmethyl 27
Azodrin 39
Bromacil 43
Captan 46
Carbofuran 55
Chlorpyrifos 57
Ciodrin 62
D.eneton 65
Diazinon 75
Dicamba 93
Dimethoate 99
Dinoseb 113
Fensulfothion 120
Fenthion 121
Folpet 129
Malathion 135
Methomyl 157
Methyl Parathion 159
Monuron 175
Parathion 183
Pentachloronitrobenzene 207
Phorate 213
Simazine 221
Trifluralin 229
vi
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CONTENTS (Continued)
Appendices
B. Reactions and Potential Impurities
Aldicarb 232
Aspon .. . 243
Azinphosmethyl 249
Azodrin 257
Bromacil 261
Captan 266
Chlorpyrifos. 27A
Ciodrin 280
Demeton 286
Diazinon 291
Dicamba 300
Dimethoate 305
Dinoseb 313
Fensulfothion 317
Fenthion 323
Folpet 333
Malathion 341
Met homy 1 348
Parathion 353
Pentachloronitrobenzene 358
Phorate 361
Simazine 366
Monuron 371
Trifluralin 378
vii
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FIGURES
Number
Page
1 GC-MS of Technical-Grade Parathion 11
2 GC-MS of Technical-Grade Methyl Parathion 12
3 GC-MS of Technical-Grade Malathion 14
4 GC-MS of Technical-Grade Phorate 15
5 GC-MS of Technical-Grade Chlorpyrifos 16
6 GC-MS of Technical-Grade PCNB 17
7 GC-MS of Technical-Grade Folpet 19
8 GC-MS of Technical-Grade Trifluralin 20
9 GC-MS of Technical-Grade Dicamba 21
B-l Synthesis of Aldicarb 232
B-2 Synthesis of Aspon 243
B-3 Main Reactions in the Preparation
of Azinphosmethyl 249
B-4 Synthesis of Azodrin 257
B-5 Synthesis of Bromacil 261
B-6 Main Reactions in the Preparation of Cap tan 266
B-7 Synthesis of Chlorpyrifos 274
B-8 Alternate Synthesis of 3,5,6-Trichloro-2-
Pyridinol 275
B-9 Synthesis of Ciodrin 280
B-10 Synthesis of Demeton 286
B-ll Synthesis of Diazinon. ....... 291
B-12 Synthesis of Dicamba 300
B-l3 Synthesis of Dimethoate 305
B-14 Alternative Syntheses of Dimethoate 306
B-l5 Synthesis of Dinoseb 313
B-16 Synthesis of Fensulfothion 317
B-17 Alternate Synthesis of Fensulfothion 318
B-18 Synthesis of Fenthion 323
B-19 Main Reactions in the Preparation of Folpet 333
B-20 Synthesis of Malathion 341
B-21 Synthesis of Methomyl 348
B-22 Main Reactions in the Preparation of
Methyl Parathion and Parathion 353
B-23 Synthesis of PCNB 358
B-24 Synthesis of Phorate 361
B-25 Synthesis of Simazine 366
B-26 Synthesis of Monuron 371
B-27 Alternate Syntheses of Monuron 372
B-28 Synthesis of Trifluralin ..... 378
viii
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TABLES
Number Page
1 Technical-Grade Pesticides Included
in the Program 6
2 Purity of Technical-Grade Pesticides 9
B-l Reactions Occurring During Aldicarb Production 233
B-2 Possible Contaminants in Aldicarb 235
B-3 Reactions Occurring During Production of Aspon 244
B-4 Possible Contaminants in Aspon 246
B-5 Reactions Occurring During Production
of Azinphosmethyl 250
B-6 Possible Contaminanats in Azinphosmethyl 252
B-7 Reactions Occurring During Production
and Storage of Azodrin 258
B-8 Possible Contaminants in Azodrin 259
B-9 Reactions Occurring During Production
of Bromacil 262
B-10 Possible Contaminants in Bromacil 263
B-ll Reactions Occurring During Production of Captan 267
B-12 Possible Contaminants in Captan 268
B-l3 Reactions Occurring During Production of
Chlorpyrifos 276
B-14 Possible Contaminants in Chlorpyrifos 278
B-15 Reactions Occurring During Production and
Storage of Ciodrin 281
B-16 Possible Contaminants in Ciodrin 283
B-17 Reactions Occurring During Production of Demeton 287
B-18 Possible Contaminants in Demeton 289
B-19 Reactions Occurring During Production
and Storage of Diazinon 292
B-20 Possible Contaminants in Diazinon 294
B-21 Reactions Occurring During Production of Dicamba 301
B-22 Possible Contaminants in Dicamba 302
B-23 Reactions Occurring During Production
and Storage of Dimethoate 307
B-24 Possible Contaminants in Dimethoate 309
B-25 Reactions Occurring During Production of Dinoseb 314
B-26 Possible Contaminants in Dinoseb 315
B-27 Reactions Occurring During Production of Fensulfothion . . . 319
B-28 Possible Contaminants in Fensulfothion 320
B-29 Reactions Occurring During Production on Fenthion 324
ix
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TABLES (Continued)
Number Page
B-30 Possible Contaminants in Fenthion 328
B-31 Reactions in Production and Storage of Folpet 334
B-32 Possible Contaminants in Folpet 336
B-33 Reactions Occurring During Production of Malathion 342
B-34 Possible Contaminants in Malathion 343
B-35 Reactions Occurring During Production and Storage
of Methomyl 349
B-36 Possible Contaminants in Methomyl 351
B-37 Reactions Occurring During Production of
Parathion and Methyl Parathion 354
B-38 Possible Contaminants in Parathion and
Methyl Parathion 356
B-39 Possible Contaminants in PCNB 359
B-40 Reactions Occurrring During Production of Phorate 362
B-41 Possible Contaminants in Phorate 363
B-42 Reactions Occurring During Simazine Production 367
B-43 Possible Contaminants in Simazine 368
B-44 Reactions Occurring During Production of Monuron 373
B-45 Possible Contaminants in Monuron 374
B-46 Reactions Occurring During Production of Trifluralin .... 379
B-47 Possible Contaminants in Trifluralin 380
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SECTION 1
INTRODUCTION
Various pesticides which have been widely and effectively used for
many years (e.g. DDT, heptachlor, and chlordane) have been shown to be very
persistent and harmful to man or the environment. For this reason the
Environmental Protection Agency has restricted the use of such materials in this
country. Users have- been forced to select substitute pesticides to do the
job that was previously done by the restricted materials. As more information
is obtained about the long-range biological effects of various pesticides
additional materials will undoubtedly be brought under stricter control or banned
for specific uses.
Although the EPA is dedicated to the protection of the environment, it
recognizes that farmers and other users need the protection afforded by
pesticides. Therefore, when a pesticide is banned for use in controlling a
pest with significant economic, ecologic or human health consequences, a
substitute must be found to replace it. One of EPA's concerns is that the
substitute pesticide authorized may be as hazardous or more hazardous than
the material it replaced. Consequently EPA has established a substitute
chemicals program involving an in-depth study of a large number of pesticides.
The study reported here involved 35 pesticides included in the EPA
substitute chemicals program. The primary objective of the study was the
identification of harmful impurities present in certain technical-grade
materials.
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SECTION 2
CONCLUSIONS AND RECOMMENDATIONS
Any technical-grade chemical is expected to contain numerous by-products
or impurities at the one percent (10,000 yg/g) level or lower. Our analytical
studies have shown that technical-grade pesticides are no exception in that
numerous impurities were detected at the 100 to 10,000 yg/g level. The
theoretical studies have shown that there may be dozens or even hundreds of
different compounds present as impurities in a given pesticide at levels
above 1 yg/g. Some of those compounds, e.g. the dioxins that may be present
in trace amounts in dicamba and chlorpyrifos and the diisopropylnitrosamine
that may be present in trace amounts in trifluralin, are highly toxic and/or
carcinogenic.
Several different experimental approaches can be used to study the
potential hazard of a technical-grade chemical. The most widely used approach
involves biological studies of the technical-grade material under a variety
of laboratory conditions to simulate different types of environmental
exposure. This is a very reasonable and realistic approach in that it is
based on the assumption that any impurity, no matter how hazardous it may
be by itself, will exert the same effect under the laboratory conditions
that it will under the field conditions of actual use. Any synergistic or
antagonistic effects of the various impurities are automatically built into
the experiment whether such effects are known or not.
However, the determination of long-term effects, for example carcinogenic
effects, fertility effects, and food chain effects, takes many years and is
very costly by the above approach. Consequently such long-term studies are
frequently incomplete or simply omitted. A classic example is the case of
2,4,5-T in which the very persistent and highly toxic impurity, tetrachloro-
dibenzodioxin (TCDD), went undetected for many years.
There are several alternative approaches to detecting such components
in a technical-grade chemical that should be considered. One approach is an
extensive analytical study to determine all trace components present at levels
above 1 ppm. Preparative gas chromatography and liquid chromatography would
be used to concentrate the Impurities. Analytical separations would be
carried out by glass capillary column gas chromatography or high-pressure
liquid chromatography. Identification of components would be made by mass
spectrometry, n.m.r. spectrometry, and/or infrared spectrometry. After the
components were identified their potential hazard would be estimated based on
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available information or on subsequent biological studies. Obviously a great
deal of time and money could be spent on such an approach; however, a few
month's effort on a technical-grade chemical could be very informative.
The GC-MS studies used in the current program were within the scope of
this approach. Unfortunately this was a minor portion of the total program
and was performed only as a superficial screening. There was no pre-
concentration of the impurities and liquid chromatography was not used at
all. For future work using this approach we highly recommend the use of
high-pressure liquid chromatography (HPLC) and glass capillary column gas
chromatography. The use of HPLC will permit the fractionation of all com-
ponents present including nonvolatile components and components that may
thermally degrade during gas chromatography. The use of glass capillary
column gas chromatography will provide much better resolution of components
and improve the chances of identifying a component by mass spectrometry.
Another approach involves analytical studies to follow-up on theoretical
evaluations. This would involve, for example, separation procedures in
conjunction with GC-MS studies to determine the amount of specific dioxins
in chlorpyrifos, dicamba, and parathion and the amount of diisopropylnitros-
amine in trifluralin. This could be done with a minimal amount of effort.
We recommend that it be included in future studies.
A third approach, and the one that we recommend most highly, involves
a combination of separation procedures and in vitro bioassay. In using this
approach various modes of high-pressure liquid chromatography would be used
to separate impurities into fractions with little likelihood of decomposition.
Each fraction would be assayed using in vitro mammalian cell toxicity assays
and the Ames Salmonella mutagenicity assays. Active fractions would be
subfractionated. Only those subfractions which showed significant activity
would be analyzed in detail to identify the active component(s). This
approach would drastically reduce the amount of analytical effort required
for a material yet would permit the detection and identification of most of
the potentially hazardous components. It is a much more cost effective approach
than the first approach which requires a very extensive analytical study.
We highly recommend that this approach be used in future programs.
The assay results showing product purity for materials stored at -20 °C
were of dubious value. There is, however, considerable merit in studying
the rates of decomposition under ambient conditions or at somewhat elevated
temperatures. It might be better to study formulated materials, which are
more subject to adverse storage conditions, than full-strength technical-
grade material in this respect. By studying degradation at ambient or some-
what elevated temperatures not only would the changes be much more pronounced
and thus simplify the analytical problem of detecting real differences but
the resulting data would relate to actual storage conditions being used.
Certainly degradation products do form in most cases under normal storage
conditions and those products could represent a considerably greater environ-
mental hazard than the freshly prepared product. We therefore recommend
that storage stability studies be carried out under ambient and elevated
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temperatures using for comparison purposes reference samples stored at -75 °C.
We further recommend that the storage stability studies be combined with
high-pressure liquid chromatography separations and a in vitro bioassay
program as already described to give a particularly cost effective program.
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SECTION 3
PESTICIDE REPOSITORY
Thirty-five different pesticides were included in the overall program.
These are listed in Table I which also shows which tasks were completed for
each material. Samples of technical-grade material for all except aldicarb
were acquired and stored. The materials were generously supplied by the
manufacturers identified in Table 1 upon request at no cost to the project.
The amounts obtained for each material ranged from 2 to 25 kg. Most of the
material was repackaged in amber glass screw-cap bottles of three different
sizes to hold approximately lOg, lOOg, or 500g each. The bottles were
thoroughly cleaned and Teflon® liners inserted in the caps prior to use
to avoid contamination. The arsenic compounds, two of which were in aqueous
solution, are reportedly stable indefinitely at 25 °C and were stored at
ambient conditions. All of the other materials were stored in freezers at
-20 °C. Each bottle was sealed in a individual polyethylene bag containing
indicating Drierite^B)to prevent hydrolysis. The bags were placed in one-
gallon paint cans as a precaution against breakage and spillage.
The main purpose of this repository was to supply material to other
EPA contractors. By having a single lot of each pesticide stored under
conditions that would prevent any significant decomposition, each EEA
contractor studying a given pesticide would be supplied identical material.
When a request was received, the appropriate size container in its polyethylene
bag could be shipped out immediately since no sample transfer was required.
The shipments were handled in accordance with Hazardous Materials
Regulation 49 CFR parts 171-177. All of the materials were classed as
Poison B. We conformed to DOT Regulation 173.358, which pertains to materials
such as liquid parathion. Parathion is representative of the most hazardous
pesticides in the repository. The bottle caps were secured by friction tape
and the bottles were packed in vermiculite in fiber drums (28 cm inside diameter,
Spec. 21C, DOT Regulation 178.224). This also is in accordance with IOTA
Packing Note 628.
Shipment was made by either Federal Express or motor freight. A "Poison"
label was placed on each outer shipping carton. For Federal Express shipments,
their hazardous materials shipping form was completed. For motor freight
shipments a certification of compliance was stamped on the shipping bill.
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XABIJE 1. TECHNICAL-CKADe PESTICIDES INCLUDED IN THE PROGRAM
No.
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
MM
Acephate
Aldlcarb
A* poo
Azlnphoi-Mthyl (CuChlon)
Acodrln
Brooacil
Cacodylllc Acid
Captan
Carbofuran
Chlorpyrlfoi (Duraban)
Clodrln
D la* too
Diaz loon
Dlcaaiba
Dlaethoate
Dinoeeb
Dlaulfoton
DSMA
Fenfulfothlon (Daaanlt)
Fenthlon
Folpat
Fonofot (Dyfonate)
Halathlon
ttochoayl
Hethoxycblor
Methyl Paracblon
Moouroa
MS MA
Parathlon
PCNB
Phorate (Thlawt)
Siduron
Sluzlnc
Triehlorfon
Trlflurallo
Bourc* of
Material (or
Hcpoaicory
Chevron
Stauffar
Ch«M|O
Shall
DuPont
Aaaul
Chevron
PMC
Dow
Shall
Chaaagro
Clba^clyj
Valalcol
Cyanaatld
Dow
Cheawgro
Anaul
Chaaagro
Cbaoagro
Chevron
Stauffar
Cyaaaadd
DoPont
DuPont
Honaaoto
K«rr-McO«
Stauffar
DuPont
Anaul
Monaanto
Olln
CyMaald
DuPont
Clba-Gelgy
Cheaagro
Elanco
Literature
Searched
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
Theoretical
Evaluation
Made
X
X
X
X
X
X
X
X
X
1
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
Peatlclde
Study Parity
Report Aciayed
laaued by CC
X
X
X
X X
X X
X X
X X
X
X
X X
X
X
X
X X
X
X X
X
X X
X X
X X
X X
X X
lapurltlei
Analyzed
by CC
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
lapurltie*
Analysed
by CC-MS
X
X
X
X
X
X
X
X
X
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SECTION 4
THEORETICAL EVALUATIONS
Literature references were collected on methods of synthesis,
impurities found, and methods of analysis for most of the 35 pesticides
through a search of Chemical Abstracts. The references are given in
Appendix A.
On the basis of the literature describing the methods of synthesis
and impurities found and on the basis of training and practical experience
in organic chemical synthesis, flow sheets showing the synthesis routes of
many of the pesticides were prepared. Tabulations of the types of reactions
possible and the possible by-products (contaminants) resulting from those
reactions were also prepared. The likelihood of a possible by-product being
present as an Impurity in the final technical-grade product was estimated
on the basis of the likelihood of its precursor being consumed by a subsequent
reaction, and the likelihood of the impurity being removed during a purifi-
cation step. The estimates consisted of assigning one of three different
concentration ranges: (1) probably present only at levels below 1 'ug/g,
(2) probably present at levels above 1 ug/g but below 100 ug/g, and
(3) probably present at levels above 100 ug/g.
In most cases the list of theoretically possible but very unlikely
impurities is incomplete and is limited by practical considerations to
include only the most likely impurities. Positional Isomers are often grouped
together although it is recognized that certain compounds in such a group
will be much more likely than others. For the many organophosphorus pesticides,
a wide spectrum of monomeric and dlmeric pentavalent and trlvalent phosphorus
compounds containing oxygen and/or sulfur is possible. Although many of
these compounds may be formed during the manufacturing process, they may also
be formed by hydrolysis, oxidation, and/or disproportionation during storage.
The synthesis schemes, including alternate routes in many cases,
tabulations of the types of reactions possible, and tabulations of possible
contaminants in many of pesticides studied are given in Appendix B. A summary
of which pesticides were included in the theoretical evaluation has been
given in Table 1.
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SECTION 5
ANALYTICAL STUDIES
GC DETERMINATION OF IMPURITIES
The major impurities present in many of the technical-grade pesticides
were studied using gas chromatography alone and in some cases in combination
with mass spectrometry. Since the main objective of this task was the
detection of as many impurities as possible rather than the determination
of gross amounts of the pesticide a very concentrated solution (10 percent)
was used and the gas chromatograph was operated at as high a sensitivity
as practical. The GC analyses were performed using a Varian Model 1740
gas chromatograph having a flame ionization detector and fitted with a
3-m x 2-mm I.D. glass column packed with 3% OV-17 on 100-120 mesh Gas-Chrom Q.
The column temperature was programmed from 60 ° to 300 °C at 8°/min. The
injector was maintained at 200 °C and the detector at 310 °C. The nitrogen
carrier gas flow was 30 ml/min. In most cases carbon disulfide was used as
a solvent to minimize interference from the solvent peak. For those compounds
that were insufficiently soluble in carbon disulfide (e.g. captan and folpet)
N,N-dimethylformamide (DMF) was used as the solvent. On-column injection
of a 2 pi sample was used.
The quantitative values were based on peak areas obtained by computer
integration. The response factors for the impurities were assumed to be
the same as that of the pesticide in each case. It was further assumed that
all of the components present were detected by the GC analysis and the sum
of the areas of all of the peaks was equated to 100 percent. Although it
is recognized that both of the above assumptions could be in error by a
factor of 2, an error of that magnitude would not be great enough to affect
the interpretation or usefulness of the data.
The amounts of impurities found in 19 of the technical-grade materials
by GC analysis are given in Table 2 . The results show that in most cases
there are numerous impurities present at the 100 yg/g level (0.01%) or
greater and frequently there are impurities present at levels greater than
1%. This is to be expected of course in any technical-grade chemical. The
important point is that the presence of the impurities should be recognized
and the potential hazards associated with the impurities should be assessed.
GC-MS DETERMINATION OF IMPURITIES
One approach to assessing the potential hazards associated with the
impurities present in technical-grade pesticide involves their identification
8
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TABLE 2. PURITY OF TECHNICAL-GRADE PESTICIDES
Purity of Technical Sample
Found by GC
Pesticide Manufacturer
Acephate Chevron
Aspon Stauffer
Azodrin Shell
Broaacil DuPont
Captan Chevron
Chlorpyrifos Dow
Clodrln Shell
Diazinon Clba Geigy
Dlcaaba Velsicol
Dimethoate Cyanamid
Dlnoseb Dow
Disulfoton Chemagro
Penthlon Chemagro
Folpet Chevron
Fonofos Stauffer
Malathlon Cyanamid
Methozychlor DuPont
Methyl parathion Monsanto
Methyl parathion Kerr-McGee
Methyl parathion Stauffer
Parathion Monsanto
PCNB Olin
Phorate Cyanamid
Trif luralin Elanco
a. Not available.
b. Conducted during the period of
c. Conducted during May and June,
d. Supplied by EPA.
c. Not analyzed during this perim
-------
by combined gas chromatography-mass spectrometry. This method was used to
study seven of the pesticides.
The gas chromatographic conditions used for the GC-MS studies were
similar to those described for the GC studies. Finnigan Models 1015 and
3200 quadrupole mass spectrometers equipped with electron Impact and chemical
ionization sources, respectively, and coupled to Finnigan Model 9500 gas
chromatographs were used for this work. The mass spectral conditions as
well as the data output were controlled by a Systems Industries Model 150
interactive computer system. Methane was used as the carrier gas for the
chemical ionization (CI), which was used to obtain molecular weight data
and a minimum of fragmentation. Helium was used as the carrier gas for the
electron impact (El) to give fragmentation patterns to support the tentative
identification resulting from the CI work.
Reconstructed gas chromatograms were obtained based on the total ion
intensity of each individual mass spectrum. Reference El mass spectra
were obtained from the literature whenever possible. Computerized spectral
matching using the original Aldermaston data tape (1972) of 9500 reference
El mass spectra was also applied. The identifications made were based on
a combination of molecular weight data, fragmentation patterns, reference
mass spectra, gas chromatographic retention times, and a knowledge of
expected impurities predicted by the theoretical evaluations.
Parathion
Ten of the 19 impurities detected in technical-grade parathion by GC
analysis were tentatively identified by mass spectrometry. The Identities
are indicated on the reconstructed gas chromatogram, Figure 1, along with the
amounts present. All of the ten are components predicted to be present
from the theoretical evaluations.
The phosphoryl chloride was an intermediate which we had expected to
be more completely hydrolyzed. The three ethyl phosphates were expected
from the reaction of ?2S5 with ethanol. The £-nitrophenol was an inter-
mediate that was expected. The £-nitrophenetole was formed by the reaction
of chloronitrobenzene with ethanol. The two minor parathion isomers are
very likely a thiolo compound and an ortho-nitro compound. Reference
materials corresponding to the impurities or model compounds were not avail-
able to help in determining the isomeric identities. The dithio analog of
parathion found was also an expected impurity.
Methyl Parathion
The results from the GC-MS study of methyl parathion were similar to
those found for parathion. The manufacturing process for methyl parathion
is essentially the same as that for parathion except that methyl alcohol is
used instead of ethyl alcohol. Seven of the impurities analogous to those
found in parathion were identified. These are indicated on the reconstructed
gas chromatogram given in Figure 2.
10
-------
PARATHION
0.2*
8
R.
8.
<•
-»«.
0.2%
(C2H50)2(C2H5S)PS
R.
0.4%
isomer of
Paraehion
(C2H50)2(C2H5S)PO
1.7%
isomer of
Parathlon
0.06%
Dithio
analog
of
(iPARATHION
C 1C 23 30 «Q SB 60 TO W 03 108 118 1M 130 1« 1HS 1BJ 170 198 J93 200 JJO 253 ZX ?.*4 JCfl r>- 273 ; -J ?c 3« 3:3
FIGURE 1. GC-MS OF TECHNICAL-GRADE PARATHION
-------
METHYL PARATHION
»-*
ro
s
"1
R.
1.5%
Isomer of
fethyl Parathion
\
isomer of
Methyl Parathion
0.022
fDlthlo
/ analog
of
METHYL
\PARATHION
B 18 2S 3D 1C 88 SB IB *B 38 10B 11B 12B 130 1« ISO ICO 170 1« t9B 200 210 22B Z30 MB ZBB 2BB 77B
FIGURE 2, GC.MS OF TECHNICAL-GRADE METHYL PARATHION
-------
Malathion
Malathion is another common organophosphate Insecticide. In addition
to the various possible phosphorus-containing impurities derived from the
reaction of methanol with ?2S5 there is the very likely possibility of
impurities derived from maleate intermediates and hydrogen sulfide or
methyl mereaptan adducts.
Eight components were identified, including two methyl phosphates, a
pyrophosphate, diethyl maleate, and the hydrogen sulfide and methyl mercaptan
adducts of diethyl maleate. The minor malathion isomer found is probably the
thiolo compound. The identified components and the amounts found are
indicated on the reconstructed gas chromatogram given in Figure 3.
Phorate
Phorate, also known as Thimet^, is an organophosphate insecticide
which requires formaldehyde and ethyl mercaptan in the manufacturing process.
In addition to the formation of the usual phosphate and pyrophosphate
by-products, it is quite likely that the hydroxymethyl intermediate will
react with a second molecule of the dithioate to give a bis-phosphoryl com-
pound or react with the ethyl mercaptan with loss of water instead of loss
of hydrogen sulfide to form the ethoxy analog. Seven different phorate
impurities were identified by GC-MS analysis. These were four ethyl
phosphates, a pyrophosphate, the ethoxy analog and the bis-phosphoryl compound.
These components and the amounts found are indicated on the reconstructed
gas chromatogram given in Figure 4.
Chlorpyrifos
Chlorpyrifos, also known as Dursban*•**•; is an organophosphate insecti-
cide analogous to parathion but prepared from 3,5,6-trichloro-2-pyridinol
instead of £-nitrophenol. In addition to the usual phosphate and pyrophosphate
by-products possible, there is the possibility of forming substituted
pyridines and dipyridodioxins during manufacture. The impurities actually
identified by GC-MS included two ethyl phosphates, a pyrophosphate, the
intermediate trichloropyridinol, an isomer of chlorpyrifos (probably the
thiolo isomer), and a tetrachloro analog of chloropyrifos. These are shown
in Figure 5.
PCNB
Pentachloronitrobenzene (PCNB) is one of the purest pesticides found
in this study. It is prepared by the chlorination and nitration of benzene.
The primary impurities expected are, therefore, various other chlorinated
and nitrated benzenes. Four such compounds were found by GC-MS analysis as
shown in Figure 6. Although trace amounts of sulfonic acids, biphenyls,
biphenylenes, dibenzodioxins, dibenzofurans, and diphenyl ethers are
theoretically possible as by-products, none was found.
13
-------
0.9%
MALATHION
0.2%
HSCHCOOC2H5
1.0%
(CH30)2(CH3S)PS
0.3%
(CH30)2P(S)SP(S)(OCH3)2
0.3%
CH3SCHCOOC2H.
5.6?
isomer of
MALATHION
/
W GO 60 78 80 SO 100 110 120 130 :*J ISO 1R3 f?0 !fi8 190 MB US ZW 23B 219 ZSO 2iO ZW 28B 23B 9
FIGURE 3. GC-MS OF TECHNICAL-GRADE MALATHION
-------
PHORATE
8
v*
S.
S.
R.
0.9%
1.1%
(C2H50)2(C2H5S)PS
0.7%
(C2H50)2P(S)SP(S) (OC
0.4%
0.2%
10 2Q 3d 10 SB 69 70 80 90 IOB DO 120 130 110 ISS 160 170 ISO 190 200 210 220 230 210 250 260270
SPECHU1 KJM36R
FIGURE 4. GC-MS OF TECHNICAL-GRADE PHORATE
-------
0.2%
0.2%
0.3%
(C2H50)2P(S)OP(S)
0.02%
Tetrachloro
analog of
CHLORPYRIFOS
CHLORPYRIFOS
\
0.1%
Isomer of
CHLORPYRIFOS
no us us OB
FIGURE 5. GC-MS OF TECHNICAL-GRADE CHLORPYRIFOS
-------
PCNB
8
*••
S-
8.
S
8.
|S-
**.
IB-
IS
Vrm IM LM t-i ' -- »1
B 2SO 278 290 290 300 310. 320
FIGURE 6. GC-MS OP TECHNICAL-GRADE PCNB
-------
Folpet
Folpet is a fungicide prepared from phthallmide and perchloromethyl
mercaptan. In addition to derivatives of phthalic anhydride, derivatives
of maleic anhydride and oxalic acid can be formed during the oxidation step
in the initial part of the manufacturing process. Various sulfenyl, sulfinyl,
and sulfonyl impurities are possible as well as acids, amides, imides,
chloroamides, chloroimides, and maleic adducts. The major impurities
found in the GC-MS study were phthalic anhydride and phthalimide. The
N-chlorooxamic acid found was one of the least expected by-products. A
small amount of elemental sulfur was also found. The reconstructed gas
chromatogram showing the contaminants found is shown in Figure 7,
Trifluralin
Trifluralin is a widely used herbicide prepared from 4-chloro-3,5-dinitro-
benzotrifluoride and diisopropylamine. During the overall process including
the preparation of the benzotrifluoride there are possibilities for the
formation of all sorts of benzene derivatives having chloro, fluoro, nitro,
methylol, carboxyl, aldehyde, hydroxyl, ether, amino, and/or substituted
amino functionalities. Although 14 components were detected by the GC
analysis only six components were identified in the GC-MS study. These were
two chloro compounds and four trifluralin isomers as indicated in Figure 8.
Dicamba
Dicamba (3,6-dichloro-2-methoxybenzoic acid) is an herbicide prepared
by the methylation of the corresponding hydroxybenzoic acid. Various benzene
derivatives having hydroxyl, chloro, and/or carboxyl functionalities are
possible as by-products as well as chlorinated dibenzodioxins. The impurities
identified by the GC-MS studies included the methyl ester of dicamba, the
.methyl ester of the hydroxy analog, a dimethoxychlorobenzene, and a dichloro-
methoxybenzene. These are indicated on the reconstructed gas chromatogram
in Figure 9.
GC ASSAY OF PRODUCT PURITY
One of the tasks of this program requested by the Project Officer was
the assay of the product purity of some of the materials before and after
being stored at -20 °C for a period of time. This study would compare the
rate of degradation of a technical-grade sample to that of a reference sample
when both are stored at -20 °C. An indication of the presence of impurities
which catalyze degradation would thus be obtained.
In this work an accuracy of GC quantification of better than ± 5 percent
was desired. Only the GC peak of the pesticide itself was of interest.
Therefore, a much more dilute solution was used than for the study of
impurities. The solutions were prepared by dissolving 10 to 20 mg of
material in DMF containing an appropriate hydrocarbon standard to give a
solution containing 20 mg/ml. This solution was then diluted with carbon
disulfide to give a solution containing 2 mg/ml (0.2%). By using DMF
18
-------
vo
10.92
PHTHALIMIDE
N-CHLOROOXAMIC ACID
(HOOCCONHC1)
1.0%
PHTHALIC ANHYDRIDE
FOLPET
IB as jo « as SB te H SB IBB no 120 la no iss ica no in :SB zap jiu JM 230 31? SB 20 zw ao 20 ao a-.a
FIGURE 7 . GC-MS OF TECHNICAL-GRADE FOLPET
-------
NJ
O
0.3%
TRIFLURALIN
1.1%
isonars of
TRIFLURALIN
8.
R.
8.,
0.1%
H (CF )(N02)2C1
0 JO 20 30 10 BO *JJ 10 W 90 JOB 110 JJB 130 ilfl
«0 id) ICO 110 180 199 209 210 2X8
FIGURE 8. GC-MS OF TECHNICAL-GRADE TRIFLURALIN
-------
0.4%
C6H2C12(OCH3)(COOCH3)
N>
<0.1X
e6H2ci2(OH)coocH3
DICAMBA
-o «c jc IT \-.t :=• :x :ta :K 10 r*a :n :r MS :-.; =E no
FIGURE 9. GC-MS OF TECHNICAL-GRADE DICAMBA
-------
initially for dissolving the hydrocarbon standard variations in the concent-
ration of the standard resulting from solvent evaporation were avoided.
The use of carbon disulfide minimized interference from the solvent peak.
The use of the more dilute solution avoided overloading of the GC column
and minimized ghosting effects.
In order to achieve adequate equilibration of the GC injector and
column and thus obtain good quantitative values, numerous GC runs were
made. For each set of runs for a given pesticide a blank was run initially
to make sure that no interferences from the previously assayed material
were present. Successive injections of reference samples alternated with
technical-grade samples were then made until the response levels became
reproducible. Triplicate runs of reference and technical-grade samples
were then made and the average values for the three used for calculating
the product purity. In some cases triplicate runs of reference and technical-
grade samples were required to accommodate the column before reproducible
response levels could be obtained. In such cases a dozen GC runs were re-
quired for assaying one pesticide.
Twenty-four of the technical-grade pesticides were assayed for
purity on two separate occasions using the above procedure. The results
are given in Table 2. The values obtained from the two assays were the
same within experimental error for all of the materials except acephate,
captan, and folpet. The values also agree quite well with those stated
by the manufacturer. Acephate and captan appear to have degraded somewhat
but considerable more work would be needed to prove that this is indeed
the case. The second assay for folpet was significantly higher than the
first indicating that the reference sample had degraded somewhat.*
Any further studies on degradation rates should be carried out at
various temperatures of 0 to 50 °C using reference samples stored at a
very low temperature.
The standard solutions as well as the solutions of technical-grade
material were used within two weeks of preparation and were stored
at 0 °C except during use. The pure reference samples and technical-
grade materials were stored at -20 °C. It is unlikely that any
significant degradation occurred at -20 °C. It is more likely that
the differences found resulted from decomposition of solutions,
solution preparation errors, or nonhomogeneity of samples.
22
-------
APPENDIX A
LITERATURE REFERENCES
-------
ALDICARB
1964
(1) "2-Alkylthiopropionaldehyde N-alkylcarbamoyloximes", Union Carbide
Corp., Fr. 1,377,474, Nov. 6, 1964; Chem. Abs. 63, 2900a (1965).
1966
(2) "Determination of Temik Residues in Raw Fruits and Vegetables", D. P.
Johnson, et al., J. Assoc. Offic. Anal. Chemists 49(2), 399-403
<1966); Chem. Abs. £5, 2895b (1966).
(3) "The Synthesis and Insecticidal Properties of Some Cholinergic
Trisubstituted Acetaldehyde 0-(methylcarbamoyl)oximes", K. Payne,
Jr., et al., J. Agr. Food Chem. 14(4), 356-65 (1966); Chem. Abs.
65, 9650c (1966).
(4) "Systemic Insecticides for Control of Insect Pests of Ornamentals",
John C. Schread, J. Econ. Entomol. .5.9(4), 983-4 (1966); Chem. Abs.
6£, 9655c (1966).
1967
(5) "Spectrophotometric Determination of Temik Residues in Citrus", W. R.
Heavier, et al., J. Assoc. Offic. Anal. Chem. £0(6),^1242-6 (1967);
Chem. Abs. 68, 11763f (1968). -°
1968
(6) "Mass Spectra of Some Carbamates and Related Ureas II", U. R. Benson,
et al., J. Assoc. Offic. Anal. Chem. 1968. 51(2), 347-65; Chem. Abs.
69, 2350n (1968).
(7) "Determination of Residues of 2-methyl-2-(methylthio)propionaldehyde
0-(methylcarbamoyl)oxime (UC-21149, Temik), its Sulfoxide, and its
Sulfone by Gas Chromatography", J. C. Maitlen, et al., Jr. Agr.
Food Chem. 1968. 16(4), 549-53; Chem. Abs. 69, 34712y (1968).
(8) "Detection of Cholinesterase-Inhibiting Pesticides Following
Separation of Thin-Layer Chromatograms", W. Winterlin, J. Agr.
Food Chem. 1968. 16(5), 808-12; Chem. Abs. 69, 95350a (1968).
(9) "Versatility of OV-17 Substrate for Gas Chromatography of Pesticides",
C. A. Bache. et al., J. Assoc. Offic. Anal. Chem. 1968, 51(6), 1270-1;
Chem. Abs. 2P_, 27907h (1969).
(10) "Acute Toxicity Data for Pesticides (1968)", K. H. Jones, et al.,
World Rev. Pest Contr. 1968. 7(3), 135-43; Chem. Abs. 71, 2442k
(1969).
23
-------
1969
(lOa) "Determination of Residues of Methyl- and Dimetby 1-Carhamate
Insecticides by Gas Chromatography of Their 2,4-Dinitroaniline
Derivatives", E. R. Holden, et al., J. Agr. Pood Chen. 1969. 17,
56-9; Chem. Abs. 70, 76493d (1969).
(11) "Preparation and Detection of Derivatives of Temik and its Meta-
bolites as Residues", H. Beckman, et al., J. Agr. Pood Chem.
1969, 17, 70-4; Chem. Abs. 70, 76495f (1969).
(12) "Field lonization Spectra of Some Pesticidal and Other Biologically
Significant Compounds", J. H. Damico, et al., Int. J. Mass Spectrom.
Ion Phys. 1969, 2(2), 161-82; Chem. Abs. 70, 105767d (1969).
(13) "Acute Toxicity of Pesticides", T. B. Gaines, Toxicol. Appl.
Pharmacol. 1969, 14(3), 515-34; Chem. Abs. Jl, 2521k (1969).
(14) "Rapid Method for the Extraction, Cleanup, and GLC (Gas-Liquid
Chromatographic) Determination of Toxic Residues of Temik",
Jay C. Maitlen, et al., J. Assoc. Offie. Anal. Chem. 1969, 52(4),
786-9; Chem. Abs. 71, 59977t (1969).
1970
(15) "High Resolution NMR Spectra of Pesticides. III. Carbamates",
L. H. Keith, et al., J. Assoc. Offie. Anal. Chem. 1970. 53(1),
157-79; Chem. Abs. 72, 77842v (1970).
(16) "Pesticidal Carbamate Derivatives of 2-Alkylthio (or oxy)Alkanaldoximes",
Union Carbide Corp., U.S. 3,507,965, Apr. 21, 1970; Chem. Abs. 73,
14248f (1970).
(17) "GLC Gas-Liquid ChroBatographic Retention Times of Pesticides and
Metabolites Containing Phospherus and Sulfur on Four Thermally
Stable Columns", M. C. Bowman, et al., J. Assoc. Offic. Anal. Chem.
1970, 53(3), 499-508; Chem. Abs. 73, 24179y (1970).
(18) "Determination of Some Methylcarbamate Insecticides by a.c. Polaro-
graphy and Cyclic Voltaametry", M. D. Booth, et al., Talanta 1970.
17(6), 491-8; Chem. Abs. 73, 76028t (1970).
(19) "Carbamate Bioassay Using Daphnia Magna", B. L. Parker, et al.,
J. Econ. Entomol. 1970, 63(3), 710-14; Chem. Abs. 73, 65307g (1970).
(20) "Sensitivity of Pig Liver Esterase in Detecting Twelve Carbamate
Pesticides in Thin-Layer Chromatograms", C. E. Mendore, et al.,
J. Chromatogr. 1970, 50(1), 92-102; Chem. Abs. 73, 108640e (1970).
24
-------
(21) "Improved Quantitative Method for the Determination of Aldicarb
and its Oxidation Products in Plant Materials", W. F. Carey,
et al., J. Assoc. Offic. Anal. Chem. 1970 53(6), 1296-9; Chem.
Abs. 74, 2959w (1971).
(22) "Degradation and Vertical Movement of Pesticides in the Soil",
S. Foschi, et al., Notiz, Mai. Piante 1970, 82-83, 37-49; Chem.
Abs. 74, 52465c (1971).
1971
(23) "Sensitized Photodecomposition and Photosensitizer Activity of
Pesticide Chemicals Exposed to Sunlight on Silica Gel Chromato-
plates", G. W. Ivie, et al., J. Agr. Food Chem. 1971. 19(3),
405-9; Chem. Abs. 75, 19168f (1971).
(24) "Fate and Carryover Properties of Temik Aldicarb Pesticide
(2-methy1-2-(methylthio)propionaldehyde 0-(methyIcarbamoy1)
oxime in Soil", N. R. Andrawes, et al., J. Agr. Food Chem. 1971,
19(4), 727-30; Chem. Abs. 75, 62521c (1971).
(25) "Negative Ion Mass Spectra of Some Pesticidal Compounds",
P. C. Rankin, J. Assoc. Offic. Anal. Chem. 1971 54(6), 1340-8;
Chem. Abs. 76, 69019z (1972).
(26) "Thin-Layer Chromatographic Analysis of Organophosphate Pesti-
cides in the Study of Environmental Contamination (Italian
Surface Waters)", V. Leoni, et al., Farmaco, Ed. Prat. 1971.
26(7), 383-93, Chem. Abs. 75, 128757t (1971).
25
-------
ASPON
1951
(1") "Tetraethvl Dlthionopvrophosphate and Related Tetraalkyl
Pithionopyrophosphates", A.D.F. Toy, J. Am. Chem. Soc.
4670-4 1951; Chem. Abs. 46, 7697d (1952).
1952
(2) "Tetraalkyl dithiopyrophosphates", Bayer Farbenfabriken, Ger.
848,812, Sept. 8, 1952; Chem. Abs. 47, 5424h (1953).
1953
(3) "Tetraalkyl dithionopyrophosphates", Victor Chemical Works U.S.
2,663,722, Dec. 22, 1953; Chem. Abs. 48, 13709d (1954).
(4) "Tetraalkyl pyrothiophosphates", Bayer Farbenfabriken, Ger.
896,644, Nov. 12, 1953; Chem. Abs. 49, 4011c (1955).
26
-------
AZINPHOSMETHYL
1956
(1) "New Specific Method of Detection of the Insecticide Bayer 17147
(Gusathion)", 0. Wollenberg, et al., Angew. Chem. 6&, 41 (1956);
Chem. Abs. 50, 6738c (1956).
(2) "Derivatives of Thiophosphoric Acid", A.-G. Bayer Farbenfabriken,
U.S. 2,758,115, Aug. 7, 1956; Chem. Abs. .51, 2888h (1957).
(3) "Colorimetric Determination of the Insecticide Bayer 17147
(Guthion)", 0. Wollenberg, Angew. Chem. 68, 581 (1956); Chem. Abs.
52, 18996a (1958).
1958
(4) "Spectrophotofluorometry for Pesticide Determinations",
I. Hornstein, J. Agr. Food Chem. 6, 32-4 (1958); Chem. Abs.
52, 7606i (1958). ""
(5) "Colorimetric Method for Estimation of Guthion Residues in
Cottonseeds and Cottonseed Oil", P. A. Giang, et al., J. Agr.
Food Chem. ^, 845-8 (1958); Chem. Abs. 53, 154lOi (1959).
(6) "Chromatography of Organic Insecticides. I. Separation of In-
secticides on PhenyIcellosolve-Treated Paper", T. Shishido, et al.,
Nippon Nogei-kagaku Kaishi _32., 956-60 (1958); Chem. Abs. 53, 15455f
(1959).
(7) "Determination of Guthion", I. Kawashiro, et al., Eisei Shikenjo
Hokoku No. 76, 59-60 (1958); Chem. Abs. 53, 17409k (1959).
1959
(8) "Qualitative Analysis of 17 Organophosphorous Compounds by Paper
Chromatography", A. Matsunaga, et al., Ibid. Kumamoto Med. J. 12,
214-19 (1959); Chem. Abs. 54, 11813e (1960).
(9) "Field Sampling of Alfalfa for the Estimation of Guthion
Residues", P. A. Dahm, et al., J. Econ. Entomol. J2. 791-8
(1959); Chem. Abs. 55, 22654d (1961).
1960
(10) "Colorimetric Determination of Guthion Residues in Crops",
W. R. Meagher, et al., J. Agr. Food Chem._£, 282-6 (1960);
Chem. Abs. 55, 22638 (1961).
27
-------
(11) "Changes in Official Methods of Analysis Made at the Seventy-
Fourth Annual Meeting, October 10, 11, and 12, 1960", Anon.
J. Assoc. Offie. Agr. Chemists 44, 133-60 (1961); Chem. Abs. 55,
14155f (1961).
1961
(12) "Determination of Insecticide Residues on Green and Flue-Cured
Tobacco and in Main-Stream Cigarette Smoke", T. 6. Bowery, et al.,
J. Agr. Food Chem.JJ, 193-7 (1961); Chem. Abs. 55, 21453h (1961).
(13) "Organic Phosphorus, Gusathion and Phosdrin. III. The Detection
and Discrimination of Gusathion and Phosdrin", I. Sato. Kumamoto
Med. J. 14, 1-12 (1961); Chem. Abs. 55, 24904a (1961).
(14) "The Effect of Ultraviolet Light (2537 A.) on 141 Pesticide
Chemicals by Paper Chromatography", L. C. Mitchell, J. Assoc.
Offic. Agr. Chemists 44, 643-712 (1961); Chem. Abs. 56, 3849e
(1962).
(15) "Toxicological Detection and Determination of Thiophosphoric
Acid Esters. II.", R. Fischer, et al., Pflanzenschutz Ber. ^7,
165-76 (1961); Chem. Abs. 59, 5677e (1963).
1962
(16) "Six Phosphate Pesticide Residues in Green Leafy Vegetables.
Cleanup Method and Paper Chromatographic Identification",
M. E. Getz, J. Assoc. Offic. Agr. Chemists 45, 393-6 (1962);
Chem. Abs. 57, 2637h (1962).
(17) "Esterase Inhibition Technique for the Detection of Organo-
phosphorus Pesticides", W. P. McKinley, et al., J. Assoc. Offic.
Agr. Chemists 45, 467-73 (1962); Chem. Abs. .57, 3821b (1962).
(18) "Polarographic Determination of Azinphos-Methyl Residues in
Certain Crops", J.A.R. Bates, Analyst 87, 786-90 (1962); Chem.
Abs. 58, 2776g (1963). ""
(19) "The Promising Utility of Infrared Assay of Pesticides and Their
Residues. II.", R. C. Blinn, et al., Pesticided Res. Bull. ,2(4),
3-11 (1962); Chem. Abs. 60, 13811g (1964). ""
1963
(20) "Chromatographic Identification of Some Organophosphate In-
secticides in the Presence of Plant Extracts", H. F. MacRae, et al.,
J. Agr. Food Chem. U, 174-8 (1963); Chem. Abs. 58, 11907d (1963).
28
-------
(21) "Determination of Guthion Residues on Fruits", W. S. Cox, J.
Assoc. Offie. Agr. Chemists 46, 229-33 (1963); Chem. Abs. 58,
14626d (1963).
(22) "Residues of Insecticides on Cover Crops Growing in Orchards
After Application of Organic Phosphorus Toxicants on the
Trees1'," H. Maier-Bode, Z. Pflanzenkrankh. Pflanzenschutz 7£ (8),
449-59 (1963); Cbem. Abs. 60, 4690e (1964).
(23) "Preparation of Electron Capturing Derivatives of Insensitive
Pesticides", W. H. Gutenmann, et al., J. Assoc. Offic. Agr.
Chemists 46(5), 859-62 (1963); Chem. Abs. 60, 12601f (1964).
(24) "The Acute Toxicity of Insecticides at Oral and Dermal Applica-
tion", C. Servintuna. Bitki Koroma Bullteni 3(4), 275-84 (1963);
Chem. Abs. 64, 6246e (1964).
1964
(25) "Thin Layer Chromatographic Detection of Interfering Compounds
in the Determination of Dimethyl Dithiophosphoric Acid Esters
of N-Methylbenzazimides", D. Katz, et al., J. Chromatog. 14(1),
133-5 (1964); Chem. Abs. .60, 15148h (1964).
(26) "Exposure to Guthion During Spraying and Formulating",
Z. Jegier, Arch. Environ. Health 8(4), 565-9 (1964); Chem. Abs.
61, 1159d (1964). ""
(27) "Rapid Determination of Guthion Residues on Crops", W. S. Cox,
J. Assoc. Offic. Agr. Chemists £7(2), 280-2 (1964); Chem. Abs.
61, 2388a (1964).
(28) "Analyses of Organophosphorus Pesticides", W. P. McKinley, Proc.
Can. Soc. Forensic Sci. 2(2), 433-48 (1964); Chem. Abs. 61, 7638c
(1964). ""
(29) "Applications of the Microcoulometric Titrating System as a
Detector in Gas Chromatography of Pesticide Residues", J. A.
Challacombe, et al., Residue Rev. 5, 57-72 (1963); Chem. Abs.
.61, 9975h (1964).
(30) "The Determination of Traces of Phosphoric Esters by Oscillo-
graph ic Polarography", -P. Nangniot, Anal. Chim. Acta 31(2),
166-74 (1964); Chem. Abs. 61, 12563c (1964). ""
(31) "A New Colorimetric Method for Determination of Residues of
Guthion and Ethyl Guthion and Their Oxygen Analogs", J.R.W.
Miles, J. Assoc. Offic. Agr. Chemists 47(5), 882-5 (1964);
Chem. Abs. 61, 15258h (1964). ~"~
29
-------
(32) "The Detection of Organophosphorus Pesticides on Thin-Layer
Chromatograms", P. J. Bunyan, Analyst 89(1062), 615-18 (1964);
Chem. Abs. .61, 15282f (1964). ~~
(33) "Application of the Acetylcholinesterase Inhibition Method for
Detecting Organophsphate Residues and Related Compounds in
Milk", J. E. Beam, et al., J. Dairy Sci. .47(12), 1297-1305
(1964); Chem. Abs. 62, 5797c (1965).
(34) "Detection and Separation of the Most Important Organophosphorus
Pesticides by Thin-Layer Chromatography", M. Salame, J. Chromalog.
j.6(3), 476-80 (1964); Chem. Abs. 62, 11090b (1965).
1965
(35) Identification of Trace Amounts of Organophosphorus Pesticides
by Frustrated Multiple Internal Reflectance Spectroscopy",
T. S. Hermann, Appl. Spectry. 19(1), 10-14 (1965); Chem. Abs.
62, 12387b (1965).
(36) "Separation of Mixtures and Detection of Trace Amounts of Some
Organophosphorus Pesticides in Plant Material by Means of Paper
Chromatography", J. Zadrozinska, Roczniki Panstwowego Zakladu
Hig. 16(1), 53-63 (1965); Chem. Abs. 62, 16876g (1965).
(37) "Oscillopolarographic Determination of Trace Residues of Some
Organic Phosphate Insecticides in Food Articles. I. Oscil-
lopolarographic Studies of 0,0-dimethyl-S-(4-oxobenzotriazinyl-
3-methyl) Dithiophosphate (Gusathion)", E. Szyszko, Farm. Polska
21(3-4), 81-8 (1965); Chem. Abs. 63, 7562g (1965).
(38) "Thin-Layer Chromatography and Cholinesterase Detection of
Several Fhosphorothiono Insecticides and Their Oxygen Analogs",
A. El-Refal, et al., J. Agr. Food Chem. 13(5), 477-81 (1965);
Chem. Abs. 63, 13968c (1965).
(39) "Screening Procedure for Organothiophosphate Pesticide Residues
on Fruits and Vegetables Using Microcoulometric Gas Chromato-
graphy", R. C. Nelson, J. Assoc. Offie. Agr. Chemists 48(4),
752-9 (1965); Chem. Abs. 63, 18932 (1965).
(40) "Determination of Selected Phosphoorganic Pesticides (Para-
thion, Methylparathion, Diazinon, Malathion, Gusathion, Meta-
Systox, and Dipterex) by Thin-Layer Chromatography Method",
J. Zadrozinska, Roczniki Panstwowego Zakladu Hig. 16(4), 397-
405 (1965); Chem. Abs. 64, 2684h (1966).
30
-------
(41) "A Sweep Codistlllation Cleanup Method for Organophosphate
Pesticides. II. Rapid Extraction Methods for Crops", R. R.
Watts, et al., J. Assoc. Offie. Agr. Chemists 48(6), 1158-60
(1965); Chem. Abs. 64, 8847f (1966).
(42) "Identification and Quantitative Determination of Phosphorus
Insecticides in Biological Material. II.", R. Fischer, et al.,
Arch. Toxikol. 21(2), 101-20 (1965); Chem. Abs. 64, I6554b
(1966).
(43) "Use of Thin-Layer and Semipreparative Gas-Liquid Chromatography
in the Detection, Determination, and Identification of Organo-
Phosphorus Pesticide Residues", D. C. Abbot, et al., Proc.
SAC (Soc. Anal. Chem.) Conf., Nottingham, Engl. 1965, 121-33,
discussion 133-4; Chem. Abs. 65, 192lOf (1966).
(44) "Spectrophotofluorimetric Method for Guthion Residues in Milk
and Animal Tissues", J. M. Adams, et al., J. Agr. Food Chem.
li(l), 53-5 (1966); Chem. Abs. 64, 103lOg (1966).
1966
(45) "Screening Tissues and Urine for Pesticides", M. M. Luckens,
J. Forensic Sci. 11<1), 64-73 (1966); Chem. Abs. 64, 20550c
(1966).
(46) "Gas Chromatographic Column for Pesticide Residue Analysis;
Retention Times and Response Data", J. A. Burke, et al., J.
Assoc. Offie. Anal. Chemists 49(2), 374-85 (1966); Chem. Abs.
65, 2894g (1966).
. \
*
(47) "Semiquantitative Determination of Organophosphorus Insecti-
cides by the Ring-Oven Technique with Preliminary Thin-Layer
Chroma tography", I.M.B. Celap, et al., Analyst 91(1086), 595-
7 (1966); Chem. Abs. 65, 20772h (1966). ~~
(48) "Mass Spectra of Some Organophosphorus Pesticide Compounds",
J. N. Damico, J. Assoc. Offic. Anal. Chemists 49(5), 1027-45
(1966); Chem. Abs. £6, 1834k (1967).
(49) "Electrochemical Methods for Quantitative Analysis of Pesticide
Residues", P. Nangniot, Meded. Rijksfac. Landbouwwetensch.,
Gent 1966, 31(3), 447-73; Chem. Abs. 69, 66438e (1968).
(50) "Separation and Detection of Submicrogram Quantities of Pesti-
cides by an Improved TLC Technique", H. Beckman, et al., Bull.
Environ. Contarn. Toxicol. 1(3), 78-85 (1966); Chem. Abs. 65,
7894e (1966). —
31
-------
(51) "Screening Procedure for Organothiophosphate Pesticide Residues
on Fruits and Vegetables by Microcoulometric Gas Chromatography",
R. C. Nelson, J. Assoc. Offie. Anal. Chemists 49(4), 763-6
(1966); Chem. Abs. 65, 17598a (1966). ~~
(52) "Methods for Market Control of Organophosphate Residues in
Fruit and Vegetables", Chr. Krause, Z. Pflanzenkr. Pflanzen-
schutz. 1966, 73(6), 335-45; Chem. Abs. 70, 18968b (1969).
1967
(53) "New Spray Reagents for the Selective Thin-Layer Chromatographic
Demonstration of Nitrogen Group-Containing Pesticides", W. Ebing,
Chimia £1(3), 132-3 (1967); Chem. Abs. 66, 104255r (1967).
(54) "Rapid Method for Surface Residues of Organophosphorus Pesti-
cides by Total Phosphorus", E. J. Broderick, et al., J. Agr.
Food Chem. .15(3), 454-6 (1967); Chem. Abs. .67, 20674J (1967).
(55) "A Thin-Layer Chromatographic Screening Test for Organophosphorus
Pesticide Residues", D. C. Abbott, et al., Analyst (London)
92(1092), 170-5 (1967); Chem. Abs. 67, 31604n (1967).
(56) "Sweep Codistillation Cleanup of Milk for Determination of
Organophosphate and Chlorinated Hydrocarbon Pesticides",
R. R. Watts, et al., J. Assoc. Offie. Anal. Chem. 50(3),
581-5 (1967); Chem. Abs. .67, 42609u (1967).
(57) "Sweep Codistillation Cleanup of Fortified Edible Oils for
Determination of Organophosphate and Chlorinated Hydrocarbon
Pesticides", R. W. Storherr, et al., J. Assoc. Offic. Anal.
Chem. J>0(3), 605-15 (1967); Chem. Abs. .67, 42612q (1967).
(58) "Direct Fluorescent Detection of Organothiophosphorus Pesti-
cides and Some of Their Sulfur-Containing Breakdown Products
After Thin-Layer Chromatography", T. H. Ragab, J. Assoc. Offic.
Anal. Chem. ^50(5), 1088-98 (1967); Chem. Abs. 67, 99119p (1967).
(59) "The Gas-Chromatographic Determination of Organophosphorus
Pesticides. II. A Comparative Study of Hydrolysis Rates",
J. H. Ruzicka, et al., J. Chromatogr. 31(1), 37-47 (1967);
Chem. Abs. £8, 2191r (1968).
(60) "Identification of Azinphos Methyl in Human Tissues and in
Figs", F. Sa, et al., J. Assoc. Offic. Anal. Chem. 50(6),
1258-60 (1967); Chem. Abs. 68, 20975d (1968).
(61) "A Modification of Miles' Method for Determining Azinphos-
methyl Residues in Crops", N. A. Smart, Analyst (London) £2
(1001), 779-81 (1967); Chem. Abs. 68, 38206p (1968).
32
-------
(62) "Temperature-Programmed Gas Chromatography of 20 Phosphorus-
Containing Insecticides on 4 Different Columns and its Applica-
tion to the Analysis of Milk and Corn Silage", M. C. Bowman,
et al., J. Assoc. Offic. Anal. Chem. 50(6), 1228-36 (1967);
Chem. Abs. 68, 38221q (1968).
(63) "Modified Hydrogen Flame-lonization Detector, Highly Sensitive and
Selective for Phosphates", R. V. Hoffman, Lect. Gas Chromatogr.
1966", 1967, 137-47; Chem. Abs. 70, 95709v (1969).
(64) "Decomposition of Guthion in N-Methyl-2-Pyrrolidinone and
Butyrolactone", J. C. Harvey, et al ., Advan. Chem. Ser. 1967
(Pub. 1969), No. 86, 81-90; Chem. Abs. 7Q, 105390a (1969).
1968
(65) "Enzymic Detection of Ten Organophosphorus Pesticides and Carbaryl
on Thin-Layer Chromatograms: an Evaluation of Indoxyl, Substituted
Indoxyl, and 1-Naphthyl Acetates as Substrates of Esterases",
C. E. Mendoza, et al., Analyst (London) 93 (1102), 34-8 (1968);
Chem. Abs. 68, 58668u (1968).
(66) "Nuclear Magnetic Resonance Studies of Phosphorus (V) Pesticides.
I. Chemical Shifts of Protons as a Means of Identification of
Pesticides", H. Babad, et al., Anal. Chim. Acta 41(2), 259-68
(1968); Chem. Abs. 68, 77181w (1968).
(67) "Rapid, Sensitive Residue Determination of Organophosphorus
Insecticides by Alkali Thermionic Gas Chromatography of Their
Methylated Alkyl Phosphate Hydrolytic Products", L. E. St. John,
Jr., et al., J. Agr. Food Chem. 1968. 16(3), 408-10; Chem. Abs.
69, 1855u (1968).
(68) "Extraction of Organochlorine and Organophosphate Insecticides
From Lake Waters", H. B. Pionke, et al., Analyst (London) 1968.
93(1107), 363-7; Chem. Abs. 69, 38663f (1968).
(69) "The Teratogenic Action of Bidrin and Other Neuroactive Agents
in Developing Hen Eggs", D. G. Upshall, et al., Biochem. Pharmacol.
1968. 17(8), 1529-42; Chem. Abs. 69, 57691e (1968).
(70) "Determination of Organophosphorus Insecticides in Plant Material",
I. Pejkovic-Tadic, et al., Hrana Ishrana 1968. 9(1), 29-31; Chem.
Abs. 69, 58436n (1968).
(71) "High-Resolution N.M.R. Spectra of Pesticides. I. Organophosphorus
Pesticides", L. H. Keith, et al., J. Assoc. Offic. Anal. Chem.
1968. 51(5), 1063-94; Chem. Abs. 69, 75849s (1968).
33
-------
(72) Polyamide Layer Chromatography of Organophosphorus Pesticides",
J. T. Huang, et al., J. Pharm. Sci. 1968. 57(9), 1620-1; Chem.
Abs. 69, 85652m (1968).
(73) "Detection of Cholinesterase-Inhibiting Pesticides Following
Separation on Thin-Layer Chromatograms", W. Wray, et al., J. Agr.
Food Chem. 1968. 16(5), 808-12; Chem. Abs. .69, 95350a (1968).
(74) "Consistency of Rst Values of Six Organophosphorus Pesticides
Resolved by Thin-Layer Chromatography in the Presence of Plant
Extracts Without Elaborate Clean-up. C. E. Mendoza, et al.,
Analyst (London) 1968. 93(1111), 688-90; Chem. Abs. 22, 10566y
(1969).
(75) "Procedure for Semiquantitative Confirmation of Some Organo-
phosphorus Pesticide Residues in Plant Extracts", P. J. Wales,
et al., Analyst (London) 1968. 93(1111), 691-3; Chem. Abs. 22,
10567z (1969).
(76) "Versatility of OV-17 Substrate for Gas Chromatography of
Pesticides", C. A. Bache, et al., J. Assoc. Offic. Anal. Chem.
1968. 51(6), 1270-1; Chem. Abs. 22> 27907h (1969).
(77) "Heterocyclic Thiophosphoric and Thiophosphonic Acid Esters",
Agripat S. A. S. African 67 04,012 July 24, 1968; Chem. Abs.
70, 77977b (1969).
(78) "Acute Toxicity Data for Pesticides (1968)", K. H. Jones, et al.,
World Rev. Pest Contr. 1968. 7(3), 135-43; Chem. Abs. 21, 2442k
(1969).
(79) "Esters of Thionothiolphosphinic or Phosphonic Acids", A.-6.
Bayer Farbenfabriken, Fr. 1,528,547 June 7, 1968; Chem. Abs. 21,
3467j (1969).
(80) "Detection of Pesticides by Reversed Phase Paper Chromatography",
R. T. Wang, et al., Chung Kuo Nung Yeh Hua Hsueh Hui Chih 1968.
6(3-4), 63-8; Chem. Abs. 21. H1799c (1969).
(81) "Qualitative Analysis of Synthetic Organic Pesticides by Spot
Tests", M. Kanda, et al., Nippon Hoigaku Zasshi 1968. 22(3),
229-51; Chem. Abs. TLt 65726x (1970).
1969
(82) "Pesticides Residues. Indoxyl Acetate Spray Reagent for Fluoro-
genic Detection of Cholinesterase Inhibitors in Environmental
Samples", R. L. Schutzmann, et al., J. Assoc. Offic. Anal. Chem.
1969. 52(1), 151-6; Chem. Abs. 22» 56345d (1969).
34
-------
(83) "Pesticide Residues. Recovery of 65 Organophosphorus Pesticides
From Florisil with a New Solvent-Elation System", H. Beckman,
et al., J. Assoc. Offic. Anal. Chem. 1969. 52(2), 286-93; Chem.
Abs. 22. 86520z (1969).
(84) "Residues on Sugarcane Tissues 24 Hours After Application of
Different Formulations of Azinphosmethyl", L. Davis, et al.,
J. Econ. Entomol. 1969. 62(2), 505-6; Chem. Abs. 71. 2490z
(1969).
(85) "Acute Toxicity of Pesticides", T. B. Gaines, Toxicol. Appl.
Phannacol. 1969. 14(3), 515-34; Chem. Abs. .71, 2521k (1969).
(86) "Gas Chromatography of Organophosphorus Pesticides: Retention
Times and Response Data on Three Columns", R. R. Watts, et al.,
J. Assoc. Offic. Anal. Chem. 1969. 52(3), 513-21; Chem. Abs.
71, 12019s (1969).
(87) "Determination of Organophosphorus Pesticide Residues in River
Waters and Effluents by Gas, Thin-Layer, and Gel Chromatography",
J. Askew, et al., Analyst (London) 1969. 94(1117), 275-83;
Chem. Abs. 21, 37852w (1969).
(88) "Gas-Liquid Chromatography of Pesticides on OV-17 Stationary
Phase", V. Leoni, et al., J. Chromatogr. 1969. 43(3), 388-91;
Chem. Abs. n, 116424m (1969).
(89) "Thin-Layer Chromatographic-Enzymic Detection of Organophosphorus
Insecticides. Thin-Layer Chromatographic Behavior of Some Other
Insecticides", H. Ackermann, J. Chromatogr. 1969. 44(2), 414-18;
Chem. Abs. 21, 779lOr (1970).
(90) "Thin-Layer Chromatographic Detection of Pesticide Residues in
Fruit and Vegetables", A. Gruene, et al., Riechst,, Aromen,
Koerperpflegem. 1969. 19(11), 494, 496, 498, 500; (12), 550-4;
Chem. Abs. 12, 131197d (1970).
(91) "Chromatographic Determination of Trace Amounts of Pesticide
Residues", M. Beroza, et al., Trace Subst. Environ. Health-3,
Proc. Univ. Mo. Annu. Conf., 3rd 1969 (Pub. 1970), 331-51;
Chem. Abs. 74, 2963t (1971).
(92) "Simple and Rapid Reversed Phase Thin-Layer Chromatography of
Pesticides", R. T. Wang, et al., Hua Hsueh 1969. (4), 80-5 (Ch);
Chem. Abs. 74, 2952p (1971).
35
-------
1970
(93) "Channel Layer Chromatography, with a Rapid Spotting Technique,
for One-Stage Cleanup In Pesticide Residue Analysis", R. M.
Hetherington, et al., J. Assoc. Offic. Anal. Chem. 1970. 53(1),
146-8; Chem. Abs. 21, 77840t (1970).
(94) "Rapid Procedures for the Routine Determination of Organophos-
phorus Insecticide Residues in Vegetables. I. Determination of
Hexane-Soluble Insecticides by Gas-Liquid Chroma tography and
Total-Phosphorus Procedures", D. J. Sissons, et al., J. Chromatogr.
1970. 47(3), 328-40; Chem. Abs. 22.. 23946J (1970).
(95) "GLC Gas-Liquid Chromatographic Retention Times of Pesticides
and Metabolites Containing Phosphorus and Sulfur on Four Thermally
Stable Columns", M. C. Bowman, et al., J. Assoc. Offlc. Anal.
Chem. 1970. 53(3), 499"-508; Chem. Abs. 22, 24l79y (1970).
(96) "Detection, Separation, and Quantitative Recovery of Thirteen
Organophosphorus Pesticides on Silica Gel GF254 Thin-Layer
Chromatograms", D. C. Villeneuve, et al., J. Chromatogr. 1970.
48(3), 567-71; Chem. Abs. 22, 54922c (1970).
(97) "Simultaneous Determinations of Azinphos Ethyl, Azinphos
Methyl, and its Oxygen Analog by Gas Liquid Chromatography",
L. M. Hunt, et al., Bull. Environ. Contarn. Toxicol. 1970. 5(1),
42-6; Chem. Abs. 21• 65301a (1970).
(98) "Modified Enzymic Detection Method for Thin-Layer Chroma to-
grams of Pesticides", G. F. Ernst, et al., J. Chromatogr.
1970. 49(2), 325-8; Chem. Abs. 22» 76024? (1970).
(99) "Simultaneous Detection of Some Organophosphorous Pesticides in
Whole Wheat Flour", C. E. Mendoza, et al., Bull. Environ.
Contam. Toxicol. 1970. 5(3), 276-8; Chem. Abs. 22« 97420e (1970).
(100) "Volatilization of Insecticides From Various Substrates",
E. P. Lichtenstein, et al., J. Agr. Food Chem. 1970. 18(5),
814-18; Chem. Abs. 22. 97854z (1970).
(101) "Residue Analyses of Phosphorus-Containing Insecticides with a
Filter-Flame Photometer", H. Haub, et al., Deut. Lebensm.-
Rundsch. 1970. 66(10), 317-22; Chem. Abs. 22» 130055q (1970).
(102) "Correlations Between Phosphorus-31 NMR Chemical Shifts and
Structures of Some Organophosphorus Pesticides", R. T. Ross,
et al., Anal. Chim. Acta. 1970. 52(1), 139-41; Cham. Abs.
31000g (1971).
36
-------
1971
(103) "Method for Confirmation of Organophosphorus Compound* at the
Residue Level", M. I. Shafik, et al., Bull. Environ. Con tarn.
Toxicol. 1971. 6(1), 55-66; Chem. Aba. 2*» 1240 I4e (1971).
(104) "Simultaneous Gas Chroma tographic Determination of Chlorinated
Hydrocarbons and Organophosphates in Plant Material", G. Becker,
Deut. Lebensm.-Rundsch. 1971. 67(4), 125-6; Chem. Abs. 75. 4460w
(1971).
(105) "Organophotphorus Pesticides in Liver: Their Identification by
Gas-Liquid Chromatography (GLC)", A. Coutselinis, et al., J.
Forensic Med. 1971. 18(1), 11-14; Chem. Abs. £5, 47745k (1971).
(106) "Routine Method for the Determination of Organophosphorus
Insecticides by Thin-Layer Chromatography", 0. Antoine, at al. ,
J. Chromatogr. 1971. 58(2), 247-56; Chem. Abs. 2£, 75234m (1971).
(107) "Esterase Inhibition Technique for the Detection of Organo-
phosphorus Pesticides on Thin- Layer Chromatograms" , T. Stijve,
et al., Mitt. Geb. Lebensmittelunters. Hyg. 1971. 62(1), 25-31;
Chem. Abs. 2£, 117195g (1971).
(108) "Infrared and Ultraviolet Spectra of Seventy-Six Pesticides",
R. C. Gore, et al., J. Assoc. Offic. Anal. Chem. 1971. 54(5),
1040-82; Chem. Abs. 75, 117202g (1971).
(109) "Thin-Layer Chroma tographic Analysis of Organophosphate
Pesticides in the Study of Environmental Contamination
(Italian Surface Waters). V. Leoni, et al., Farmaco, Ed. Prat.
1971. 26(7), 383-93; Chem. Abs. j^, 128757t (1971).
(110) "Quantitative Determination of Azinphosmethyl (Guthion> in
Blueberries by Thin- Layer Chromatography and in Situ, Fluores-
cence Spectroacopy", R. W. Frei, et al., Int. J. Environ. Anal.
Chem. 1971. 1(2), 141-6; Chem. Abs. 2£, 98066t (1972).
(Ill) "Degradation Dynamics of Some Insecticides. II. Degradation of
Some Insecticides on Peach and Apricot Fruits", N. Mitic-Muzina,
et al., Zast. Bllla 1971. 22(112-113), 51-60; Chem. Abs. ]±,
136547k (1972).
(112) "Quantitative Thin- Layer Chromatography of Organothiophosphorus
Pesticides by in Situ Fluorimetry", R. W. Frei, et al. , Int.
J. Environ. Anal. Chem. 1971. 1(2), 99-111; Chem. Abs. 76,
136670V (1972).
37
-------
1972
(113) "pH-Sensitive Fluorogenic Spray Reagents. II. Quantitative
Studies with Pesticides", R. W. Frei, et al., Chromatographia
1972. 5(5), 296-300; Chem. Abs. J7, 84268u (1972).
(114) "Chemical Hydrolysis of Some Organic Phosphorus and Carhamate
Pesticides in Aquatic Environments", S. D. Faust, et al.,
Environ. Lett. 1972. 3(3), 171-201; Chem. Abs. 77» H0352p
(1972).
(115) "Thionothiolphosphoric, -phosphonic, and -phosphinic Acid
Esters", A.-G. Bayer Farbenfabriken, U.S. 3,682,910, August 8,
1972; Chem. Abs. 2Z» I40280f (1972).
(116) "Effect of Light, Temperature, and pH on the Degradation of
Azinphosmethyl", I. I. Liang, et al., J. Econ. Entomol. 1972,
65(2), 315-21; Chem. Abs. 77» 15547x (1972).
(117) "Infrared Analysis of Pesticide Formulations", S. W. Goza,
J. Assoc. Offic. Anal. Chem. 1972 55(5), 913-17; Chem. Abs.
27, 160898s (1972).
38
-------
AZODRIN
1948
(1) "Trialkyl Phosphites", Monsanto Chemical Co., U. S. 2,843,616,
July 15, 1948; Chem Abs. .53, 2090f.
1952
(2) "Acetoacetic Acid Amides", CIBA Ltd., U. S. 2,615,917, October 28,
1952; Chem. Abs. ,48, 710g.
1957
(3) "Carbamoylalkenyl Phosphorus-Containing Esters", Shell Development
Co., U. S. 2,802,855, August 13, 1957; Chem. Abs. 52, 2067.
1958
(4) "Trimethyl Phosphite", Monsanto Chemical Co., U. S. 2,848,474,
August 19, 1958; Chem. Abs. ^53, 1144c.
1964
(5) "Dimethyl 1-methy1-2-(methylcarbamoylvinyl) Phosphate", Shell Inter-
nationale Research Maatschappij, N.V. Neth. Appl. 6,403,122,
September 28, 1964; Chem. Abs. 62, 7638h.
1966
(6) "Separation and Measurement of 3-hydroxy-N, N-dimethyl-cis-crontonamide
dimethyl phosphate (Bidrin insecticide) and 3-hydroxy-N-methyl-cis-
crbtonamide dimethyl* phosphate (Azodrin insecticide) Residues in Crops
by Selective Cleanup (partition) Procedures'1, S..C'. Lau, J. Agr. Food
Chem. .14(2), 145-8 (1966); Chem. Abs. 64, 14859.
(7) "Stability of Agricultural Chemicals. I. Hydrolytic and Thermal
Stabilities of Phosphorylated Crotonamides", N. P, H. Brown, et al,
J. Sci. Food Agr. .17(11), 510-17 Q966): .Chem.. Abs. 66, 1842s (1966).
1967
(8) "Detector Cell for Measuring Picogram Quantities of Organophosphorus
Insecticides, Pyrethrin Synergists, and Other Compounds by Gas
Chromatography", W. N. Bruce, J. Agr. Food Chem. .15(1), 178-81
(1967); Chem. Abs. 66, 54499a (1967).
39
-------
1967
(9) "Automated Residue Determinations of Insecticidal Enol Phosphates",
G. Voss, et al, Meded. Rijksfac. Landbouwwetensch, Gent, 1967,
32(3-4), 877-89; Chem. Abs. 70, 18953t (1967).
(10) "Bidrin Insecticide", P- E. Porter, Anal. Methods Pestic., Plant Growth
Regul., Food Additives, 1967, 5, 213-33; ; Chem. Abs. 70, 67063m
(1969).
(11) "Azodrin Insecticide", P. E. Porter, Anal. Methods Pestic..Plant Growth
Regul., Food Additives, 1967, 5, 193-201; Chem. Abs. 70, 67063m
(1969).
1968
(12) "Nuclear Magnetic Resonance Studies of Phosphorus (V) Pesticides.
I. Chemical Shifts of Protons as a Means of Identification of
Pesticides", H. Babad, et al, Anal. Chim. Acta .41(2), 259-68 (1968);
Chem. Abs. 68, 77181w (1968).
(13) "Determination of Bidrin, Azodrin, and their Metabolites with the
Thermionic Detector", B. Y. Giang, et al., J. Agr. Food Chem. 1968,
lb(6), 899-902; Chem. Abs. _70, 2683u (1969).
(14) "Phosphinyloxycrotonyl Halides", Shell Oil Company, U. S. 3,400,177,
September 3, 1968; Chem. Abs. 70, 87064r (1969).
1969
(15) "Thin-Layer Chromatographic Determination of Bidrin, Azodrin, and
Their Metabolites",B.Y. Giang, et al, J. Agr. Food Chem. 1969, .17,
63-9; Chem. Abs. 70, 76494e (1969).
(16) "Pesticide Residues. Recovery of 65 Organophosphorus Pesticides
from Florisil with a New Solvent-Elution System'^ H. Beckman, et al,
J. Ass. Offic. Anal. Chem. 1969, 52(2), 286-93; Chem. Abs.
20, 8652Oz (1969).
(17) "Gas Chromatography of Organophosphorus Pesticides: Retention Times
and Response Data on Three Columns", R. R. Watts, et al, J. Ass.
Offic. Anal. Chem. 1969, 52(3), 513-21; Chem. Abs. n, 12019s
(1969).
1970
(18) "GLC [Gas-Liquid Chromatographic] Retention Times of Pesticides and
Metabolites Containing Phosphorus and Sulfur on Four Thermally
Stable Columns", M. C. Bowman, et al, J. Ass. Offic. Anal. Chem.
1970, 53(3), 499-508; Chem. Abs. 73, 24179y (1970).
40
-------
1970
(19) "Insecticidal Dimethyl l-methyl-2-(methylcarbarmoyl)-vlnyl Phosphate",
Shell Internationale Research MaatschappiJ N. V.jGer. Offen.
1,964,535 July 23, 1970; Chem. Abs. 73, 76656w (1970)
1970
(20) "Correlations Between Phosphorus-31 NMR Chemical Shifts and Structures
of Some Organophosphorus Pesticides", R. T. Ross, et al., Anal. Chim.
Acta 1970, 52(1), 139-41; Chem. Abs. 74, 31000g (1971)
1971
(21) "Insecticidal Dimethyl l-methyl-2-(methylcarbamoyl)-Vinyl Phosphate",
Shell Internationale Research MaatschappiJ N.V.jGer. Offen. 2,064,208
July 8, 1971, Chem. Abs. 75, 76151u (1971)
1971
(22) "Colorimetric Method for Determining Vinyl Phosphate Insecticides
Dicrotophos (Dimethy 1(2-Dimethyl Carbamoyl-1-Methyl Vinyl)Phosphate
and Monocrotophos(dimethyl(2-methy1-carbamoyl-l-methylvinyl)
Phosphate)", J. Resales, et al.,Anal. Chim. Acta 1971, 56(1), 127-35
Chem. Abs. 75, 109065z (1971) ""
1971
(23) "Insecticidal Dimethyl l-methyl-2-(methylcarbamoyl)-Vinyl Phosphate",
Shell Internationale Research MaatschappiJ N.V.^Neth. Appl. 1970
18,916 July 2, 1971; Chem. Abs. T5_ 129370y (1971)
1971
(24) "Determination of Traces of Crotonic Acid Derivatives in Air, Water,
and Biological Media", T. M. Snitkovskaya, (USSR), Tr. Vses.
Soveshch. Issled. Ostakov Pestits. Profilakt. Zagryazneniya Prod.
Pitan., Kormov Vnesh. Sredy, 2nd 1971. 197-200 Nuvacron (6923-22-4);
Chem. Abs. 78, 106843c (1973)
1972
(25) "Hydrolysis and Solvent Partition of Phosdrin and Related Organophosphates",
J. N. Seiber, et al., Bull. Environ. Contain, Toxicol. 1972. 7(2/3),
72-4 (Eng); Cbem. Abs. 77, 30117a (1972)
41
-------
1972
(26) "Titrimetric Determination of the Vinyl Phosphate Insecticides
Dicrotophos (dimethyl 2-(dimethylcarbamoyl)-l-methy1vinyl
phosphate) and Monocrotophos (dimethyl 2-(methylcarbamoyl)-l-
methylvinyl Phosphate)", J. Resales, Fresenius Z. Anal. Ghent. 1972
262(5), 361-3 (Ger).; Chem. Abs. 78, 68001s (1973)
'i*.»
1973
(27) "Reaction Gas Chromatographic Analysis of Pesticides. II On-
Column Transest^rification of Organophosphates by Methanol",
H. A. Moye, J. Agr. Food Chem. 1973, 21(4), 621-5; Chem. Abs.
79 101510c (1973)
-------
BROMACIL
1963
(1) "Uracils and Hydrouracils", E. I. duPont de Nemours & Co., Belgian
Patent 625,897, June 10, 1963; Chem. Abs.t 60, 14519c (1964).
(Equivalent of U. S. Patent 3,235,357).
1964
(2) "3-Substituted Uracils for Herbicidal Compositions", E. I. duPont
de Nemours and Co., Brit. Patent 968,661, Sept. 2, 1964; Chem. Abs.,
61, 13326g (1964).
(3) "Reductive Alkylation of Urea", E. I. duPont de Nemours & Co.,
U. S. Patent 3,161,677, Dec. 15, 1964; Chem. Abs., 62, 7649c (1965).
1965
(4) "Butylurea and Similar Compounds", E. 1. duPont de Nemours & Co.*
French Patent 1,414,196, Oct. 15, 1965; Chem. Abs., 64, 6506a (1966).
(5) "Oxazinones", E. I. duPont de Nemours & Co., French Patent 1,394,286,
April 2, 1965; Chem. Abs., 63, 4309g (1965).
(6) "Effects of Ultraviolet Light on Herbicides", L. S. Jordan et al.,
Weeds, 13 (1), 43-46 (1965); Chem. Abs., 62, 8330b (1965).
(7) "5-Halo-3,6-Disubstituted Uracils", E. I. duPont de Nemours & Co.,
French Patent 1,443,654, June 24, 1965; Chem. Abs., 66, 85798b (1967)
1966
(8) "Determination of Bromacil Residues", H. L. Pease, J. Agr. Food
Chem., 14 (1), 94-96 (1966); Chem. Abs., 64, 10311e (19b6).
(9) "Preparation of 5-Halo-3,6-Disubstituted Uracils", E. I. duPont de
Nemours & Co., U. S. Patent 3,274,196; Sept. 20, 1966; Chem. Abs.,
65, 16981a (1966).
1967
\
(10) "Bromacil", H. L. Pease et al., Anal. Methods Pesticides, Plant
Growth Regulators, Food Additives, 1967, 5^, 335-46; Chem. Abs.,
70, 76583h (1969).
43
-------
(11) "Thin-layer Chromatographic Separation, Identification, and Estima-
tion of Residues of Some Carbonate and Allied Pesticides in Soil
and Water", D. C. Abbott et al., J. Chromatog., 30 (1), 136-142
(1967); Chem. Abs., 6]_, 116051e (1967).
(12) "Method of Determining Bromacil in Soils and Plant Tissues", V. A.
Jolliffe et al., J. Agr. Food Chem., 15 (1), 174-177 (1967);
Chem. Abs., 66, 54441a (1967).
1968
(13) "Alkylation of Ureas by Some Secondary and Primary Alcohols", G. Kh.
Tyshchuk et al., Tr. Tashkent Politekh. Inst., 1968, 17-19; Chem.
Abs., 73, 109456m (1970).
(14) "Versatility of OV-17 Substrate for Gas Chromatography of Pesticides",
C. A. Cache et al., J. Ass. Offie. Anal. Chem., 51 (6), 1270-1 (1968);
Chem. Abs., 70, 27907h (1969).
(15) "Liquid Uerbicidal Uracil Concentrates", E. I. duPont de Nemours & Co.,
S. African Patent 67 07 079, Apr. 16, 1968; Chem. Abs., 2P_, 57879t
(1969).
1969
(16) "Chemical and Thermal Methods for Disposal of Pesticides", M. V.
Kennedy et al., Residue Rev., 29, 89-104 (1969); Chem. Abs., 72,
53996x (1970).
(17) "Decontamination of Pesticides in Soils", P. C. Kearney et al.,
Residues Rev., _29, 137-149; Chem. Abs., 72, 42084x (1970).
(18) "Mass Spectra of Substituted Uracils", R. W. Reiser, Org. Mass
Spectrom., 2 (5), 467-479 (1969); Chem. Abs., 71, 49068h (1969).
(19) "Determination and Separation of Some Uracil Herbicides by Thin-
Layer Chromatography", F. G. Von Stryk et al., J. Chromatog., 41
(1), 125-126; Chem. Abs., 71, 48496j (1969).
1970
(20) "Determination of Bromacil by Gas Chromatography", A. Bevenue et al.,
J. Chromatog., 46 (1), 110-111 (1970); Chem. Abs., 72, 77686x (1970).
1971
(21) "Rapid Bioassay for Photosynthetic and Respiratory Inhibitors",
B. A. Kratky et al., Weed Science, 19_ (6), 658-661 (1971); Chem.
Abs., 2§, 69030w (1972).
44
-------
1972
(22) "Chemical and Thermal Aspects of Pesticide Disposal", M. V. Kennedy
et al., J. Environ. Qual., 1 (1), 63-65 (1972); Chem. Abs., 7j6,
69170s (1972).
(23) "Mild Thermal Degradation of Pesticides", B. J. Stojanovic et al.,
J. Environ. Qual., !_ (4), 397-401 (1972); Chem. Abs., 78, 80904w
(24) "Analysis of Decomposition Products of Pesticides", M. V. Kennedy
et al., J. Agr. Food Chem., 20 (2), 341-343 (1972); Chem. Abs., 77t
1629p (1972).
(25) "Determination of Fluorine and Bromine in Halogenated Herbicide
Residues in Soil by Spark-Source Mass Spectrometry", S. C. Tong
et al., Anal. Chem., 44 (6), 1069-72 (1972); Chem. Abs., 77, 44150t
(1972).
45
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CAPTAN
1951
(1) "Parasiticidal Compounds Containing the NSCCLo Group", Standard
Oil Development Co. U.S. 2,553.770. May 22, 1951; Chem. Abs. 45,
6791i (1951).
1952
(2) "Colorimetric Determination of N-Trichloromethylthiotetra-
hydrophthalimide", A. R. Kittleson, Anal. Chem. 24, 1173-5 (1952);
Chem. Abs. 46, 10052c (1952).
(3) "A New Class of Organic Fungicides", A. R. Kittleson, Science
115, 84-6 (1952); Chem. Abs. 46, 10134d (1952).
(4) "N-(Trichloromethylthio)imides", Standard Oil Development Co.
Brit 666.636. Feb. 13, 1952; Chem. Abs. 46, 11232c (1952).
1953
(5) "Preparation and Some Properties of N-(Trichloromethylthio)
tetrahydrophthallmide", A. R. Kittleson, J. Agr. Food Chem. !_,
677-9 (1953); Chem. Abs. 48, 5852g (1954).
(6) "Preparation of N-Trichloromethylthioimides", Standard Oil Devel-
opment Co. U.S. 2.653.155. Sept. 22, 1953; Chem. Abs. ^8, 7059g
(1954).
1955
(7) "Colorimetric Determination of N-(Trichloromethylthio)-tetra-
hydrophthalimide", A. R. Kittleson, Anal. Chem. 27_, 2015 (1955);
Chem. Abs. 50, 7669f (1956).
(8) "N-Trichloromethylthioimides", Esso Research and Engineering Co.
U.S. 2.713.058. July 12, 1955; Chem. Abs. 50, 8734d (1956).
(9) "XXII. Determination of Captan Deposits", 2. J. T. Martin, et al.,
Hort. Research Sta., Long Ashton, Bristol 1955. 98-102 (Pub. 1956);
Chem. Abs. 51, 1521h (1957).
1956
(10) "Separation and Identification of Chlorinated Organic Pesticides
by Paper Chromatography. VII. Aramite, Captan, Dieldrin, Lindane,
Spergon, and Tritisan", L. C. Mitchell, J. Assoc. Offie. Agr.
Chemists 39, 484-9 (1956); Chem. Abs. 51, 2223h (1957).
46
-------
(11) "Stabilization of Chlorinated Pesticides", United States Rubber Co.
U.S. 2.760.900, Aug. 28, 1956; Chem. Abs. 51. 2226f (1957).
(12) "Determination of Captan", J. Wagner, et al., J. Agr. Pood Chem.
4^ 1035-8 (1956); Chem. Abs. 51, 4625a (1957).
1957
(13) "Changes in Methods of Analysis Made at the Seventh. Annual
[AOAC] Meeting", Anon. J. Assoc. Offie. Agr. Chemists 40, 39-78
(1957); Chem. Abs. 51, 4865i (1957).
(14) "Determination of Metals, Other Elements, and Residues in Foods",
L. L. Ramsey, J. Assoc. Offic. Agr. Chemists 40, 210-18 (1957);
Chem. Abs. _51, 6035d (1957).
(15) "Determination of Captan on Surface of Fruits and Vegetables",
D. M. Taylor, et al., J. Assoc. Offic. Agr. Chemists 40. 219-24
(1957); Chem. Abs. 51, 6035d (1957).
(16) "N-Trichloromethylthio Derivatives", Esso Research and Engineering
Co. Brit. 787.168. Dec. 4, 1957; Chem. Abs. 52, 10211d (1958).
(17) "Fungicides", Esso Research and Engineering Co. Ger. 956,639,
Jan. 24, 1957; Chem. Abs. 53, 17413 (1959).
1958
(18) "Pyridine-Alkali Reactions in the Analysis of Pesticides Containing
Active Halogen Atoms", H. P. Burchfield, et al., J. Agr. Food
Chem. £, 106-11 (1958); Chem. Abs. 52, 7607f (1958).
(19) "Separation and Identification of Chlorinated Organic Pesticides
by Paper Chromatography. XI. A study of 114 Pesticide Chemicals:
Technical Grades Produced in 1957 and Reference Standards", L. C.
Mitchell, J. Assoc. Offic. Agr. Chemists 41, 781-816 (1958); Chem.
Abs. 53, 2525b (1959).
(20) "Absorptiometric Analysis of N-(Trichloromethylthio)-4-
Cyclohexene-l,2-dicarboximlde (Captan)", H. P. Burchfield, et al.,
Contribs. Boyce Thompson Inst. 19, 411-16 (1958); Chem. Abs. 53,
3577e (1959).
(21) "Captan [Antifermentative Activity and] Detection in Wine by the
Chromatographlc Method", E. Sudario, et al., Riv. Viticolt. e
enol. (Conegliano) 11, 61-9 (1958); Chem. Abs. £3, 5582f (1959).
(22) "2-Thiazolidinethione-4-Carboxylic Acid From the Reaction of Captan
With Cysteine", R. J. Lukens, et al., Science 127_, 650 (1958);
Chem. Abs. 53_, 10177a (1959).
47
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1959
(23) "Chemical and Biological Studies on a Reaction Between Captan and
the Dialkyldithiocarbamates", R. J. Lukens, Phytopathology 49,
339-43(1959); Chem. Abs. 53, 1903lg (1959).
(24) "Characterization and Estimation of Traces of Captan", J. Roubert,
Chim. Anal. 41, 333-4(1959); Chem. Abs. 53, 2l430i (1959).
1960
(25) "Identification of Pesticide Residues in Extracts of Fruit, Vegetables,
and Animal Fats. II. Rapid Qualitative Chemical Tests for Captan
and Methoxychlor", W. P. McKinley, et al., J. Assoc. Offic. Agr.
Chemists 43, 89-91(1960); Chem. Abs. 54, 10171f (1960).
(26) "Detection of Plant Pesticides in Mixtures by Infrared Spectroscopy",
W. Fischer, et al., Z. Anal. Chem. 172 175-92(1960); Chem. Abs. 54,
I3525i (1960).
(27) "The Determination of Captan in Plant Extracts", E. Somers, et al.,
Analyst 85, 440-2(1960); Chem. Abs. 55, 4859g (1961).
(28) "The Qualitative and Quantitative Colorimetric Determination of
Captan", H. Meltzer, Deut. Pflanzenschutzdienst (Berlin) 14,
193-5(1960); Chem. Abs. 55, 8739c (1961).
(29) "Reactions of Dichlone and Captan With Thiols", R. 6. Owens, et al.,
Contribs. Boyce Thompson Inst. 20. 475-97(1960); Chem. Abs. 55.
18673f (1961).
1961
(30) "Preparation of the Fungicide Kaptan", N. N, Mel'nikov, et al.,
Zhur. Priklad. Khim. 34, 2550-4(1961); Chem. Abs. 56, 10035g (1962).
(31) "The Effect of Ultraviolet Light (2537 A.) on 141 Pesticide Chemicals
by Paper Chromatography", L. C. Mitchell, J. Assoc, Offic. Ag.
Chemists 44, 643-712(1961); Chem. Abs. 56, 3849e (1962).
(32) "Organic Fungicides-Substitutes for Copper-Containing Preparations",
N. N. Mel'nikov, et al., Khim. Prom. 1961. 692-4; Chem. Abs. 58,
471d (1963).
1962
(33) "Synthesis of the Fungicide Captan. I. Preparation of Perch lor ome thy 1-
mercaptan", T. Ambrus, et al., J.3, No. 4, 193-7(1962); Chem. Abs.
58, 5504d (1963).
48
-------
(34) "Fungicides", Japan Agricultural Chemicals and Insecticides Co.,Ltd.",
Japan. 15.145(1962) :Chem. Abs. .59, 6933a (1963).
(35) "The Promising Utility of Infrared Assay of Pesticides and Their
Residues. II", R. C. Blinn, et al., Pesticide Res. Bull. 2(4),
3-11(1962); Chem. Abs. 60, 13811g (1964).
1963
(36) "Captan In Green Vegetables", T. J. Klayder, J. Assoc. Offic. Agr.
Chemists 46, 241-3(1963); Chem. Abs. 58, 14626f (1963).
(37) "Thin-Layer Chromatography for Insecticide Analysis", K. C. Walker,
et al., J. Assoc. Offic. Agr. Chemists, 46. 250-61(1963); Chem.
Abs. 58, 14626g (1963).
(38) "Polarographic Determination of Trace Amounts of Fungicides or
Insecticides on Cultivated Plants. IV. The Polarographic Determination
of N-Trichloromethylthiotetrahydrophthalimide (Captan) and N-
Trichloromethylthiophthalimide (Phaltan)", P. Nangniot, et al.,
Bull. Inst. Agron. Stat. Rech. Gembloux 3_1(1), 110-26(1963);
Chem. Abs. 60, 12603a (1964).
1964
(39) "The Degradation of Captan, Phaltan, and Difolatan by Light",
G. Serra, Phytiat. Phytopharm J3(2), 107-10(1964); Chem. Abs.
62, 3337h (1965).
(40) "Fluorodichloromethylthio Derivatives and Their Use in Plant Protection1.',
E. Kiichle, et al., Angew. Chem. Tj&W), 807-16(1964); Chem. Abs. 62.
3973b (1965).
(41) "Thin-Layer Chromatography of a-naphthyl N-Methylcarbamate (Sevin,
Carbaryl) and Some Other Pesticides", R. Engst, et al., Nahrung
8(8), 653-64(1964); Chem. Abs. 62, 12389h (1965).
(42) "Determination of Captan by Infrared Spectrophotometry", B. Pontvianne,
Mededel. Landbouwhogeschool Opsoekingsta. Staat Gent .29(3), 1208-20(1964);
Chem. Abs. 63, 17152d (1965).
(43) "Purification.of Fungicidal Trichloromethylthio Compounds", Ger.
(East) 32,939, Nov. 16, 1964; Chem. Abs. 63, 11388d (1965).
1965
(44) "Magnitude and Stability of Captan Residues in Fresh and Preserved
Plant Products", B. Koivitoinen, et al., J. Agr. Food. Chem. 13(5).
468-72(1965); Chem. Abs. 63, I3930b (1965).
49
-------
(45) "Extraction p-Values of Pesticides and Related Compounds in Six
Binary Solvent Systems", M. C. Bowman, et al., J. Assoc. Offic.
Agr. Chemists 48(5)» 943-53(1965); Chem. Abs. 64, 4l92h (1966).
(46) "Mixed Fungicides", Chevron Research Company, U.S. 3.226,290.
Dec. 28, 1965; Chem. Abs. 64, 8055d (1966).
(47) "A Co lor ime trie Method for the Determination of Captan and Phaltan.
Residues on Grapes and Strawberries", G. Viel, Phytiat. Phytopharm.
14(3), 165-71(1965); Chem. Abs. 65, 4528d (1966).
(48) "Pesticide Residues. Identification and Quantitative Analysis of
Residual Captan and Phaltan in Wine and Grape Juice", R. Mestres,
et al., Trav. Soc. Pharm. Montpellier 25(2), 125-8(1965); Chem.
Abs. 65, 7896a (1966).
(49) "Determination of Captan and Phthalan in the Air1', T. G. Lipina,
Gigiena i Toksikol. Pestitsidov i Klinika Otravlenii, Sb. (Kiev:
Zdorov'e) 1965. 578-80; Chem. Abs. 65, 17591f (1966).
1966
(50) "Thin-Layer Chromatography of Pesticides", T. Salo, et al., Z.
Lebensm-Untersuch. -Forsch. 129(3). 149-53(1966); Chem. Abs.
64, 20546d (1966).
(51) "Gas Chromatographic Column for Pesticide Residue Analysis;
Retention Times and Response Data", J. A. Burke, et al., J. Assoc.
Offic. Anal. Chemists 49(2), 374-85(1966); Chem. Abs. 65, 2894g (1966).
(52) "Thin-Layer Chromatography of Captan and Captax", L. Fishbein, et al.,
J. Chromatog. 23(3), 476-80(1966); Chem. Abs. 65, 17626c (1966).
(53) "Detection and Determination of Chlorinated Insecticides in Biological
Materials. I. Two-Dimensional Thin-Layer Chromatography of Chlorinated
Insecticides; Principles of the Quantitative Estimation", V. Leoni,
Ric. Sci. 36(7), 632-7(1966); Chem. Abs. 66, 1851m (1967).
(54) "Electrochemical Methods for Quantitative Analysis of Pesticide
Residues", P. Nangniot, Meded. Rijksfac. Landbouwwetensch., Gent1
1966. 31(3), 447-73i Chem. Abs. 69, 66438e (1968),
1967
(55) "Determination of Captan and Phaltan Residues by Thin-Layer
Chromatography", R. Engst, et al., Nahrung .11(1), 95-100(1967)$
Chem. Abs. .67, 20660b (1967).
50
-------
(56) "Carbonyl Sulfide From the Decomposition of Captan", E. Somers,
et al., Nature 215(5097), 214(1967); Chem. Abs. 67, 72684g (1967).
(57) "Gas Chromatographic Determination of Captan Residues", W. Kilgore,
et al., J. Agr. Food Chem. J3(6), 1035-7(1967); Chem. Abs. 68,
2011g (1968).
(58) "Colorimetric Determination of Residual Captan and Phaltan in
Grape Juice and Wine", R. Mestres, et al., Ann. Fals. Expertise.
Chim. 60(674), 69-72(1967); Chem. Abs. 68, 20959b (1968).
(59) "Relation of Structure to Sensitivity in the Electron Capture
Analysis of Pesticides!1, W. L. Zielinski, -Jr., et al., J. Gas
Chromatogr, 5_(11), 552-5(1967); Chem. Abs. 68, 21156z (1968).
(60) "Refining N-(Polyhaloalkylthio)Imides of Dicarboxylic Acids",
Czech. 122.756. April 15, 1967; Chem. Abs. 68, 29442k (1968).
(61) "The Use of Polarography to Determine Small Amounts of Fungicides
or Insecticides in Deposits or Residues on Plants. VI.
Polarographic Determination of N-(l,l,2,2-tetrachloroethylthio)
Tetrahydrophthalimide or Orthodifolatan", R. Vervier, et al.,
Bull. Rech. Agron. Gembloux JZ(2), 369-76(1967); Chem. Abs. 68,
58580J (1968).
19J68
(62) "Detection and Determination of Captan in Wines by Infrared Spectro-
photometry", D. Coppini, et al., Mikrochim. Acta 1968(1). 160-6;
Chem. Abs. 68, 67794j (1968).
(63) "Chlorine Determination in Pesticides by the Diphenylsodium Method",
R. Liebmann, et al., Chem. Tech. (Berlin) 1968. 20(3), 169-70;
Chem. Abs. 69, 2062v (1968).
(64) "Thin-Layer Chromatography; Relative Migration Data (R>m)E) of
Chlorinated Pesticides", E. J. Thomas, et al., J. Chromatogr. 1968.
35(1), 119-21; Chem. Abs. 69, 18229r (1968).
(65) "Determination of Pesticide Traces in Stone Fruits", D. Vojvodic,
et al., Hrana Ishrana 1968. 9(1), 26-8; Chem. Abs. 6>9, 58435m (1968).
(66) "Gas Chromatographic Determination of Chlorinated Pesticide
Residues in Wines", M. Matta, Vini Ital. 1968. 10(54), 171-4(Ital);
Chem. Abs. 69, 66469r (1968).
(67) "Sodium Methylate Treatment of Cleaned up Plant Extracts in
Confirmation of Some Pesticide Residues by Gas-Liquid and Thin-Layer
Chromatography", C. E. Mendoza, et al., J. Assoc. Offic. Anal. Chem.
1968. 51(5), 1095-101(Eng); Chem. Abs. 69, 75626s (1968).
51
-------
(68) "Captan and Structurally Related Compounds; Thin-Layer and Gas-Liquid
Chromatography", L. H. Pomerantz, et el., J. Ass. Offic. Anal. Chem.
1968. 51(5), 1058-62; Chem. Abs. .69, 75856s (1968).
(69) "The Examination of Mixtures of Captan and Phaltan by Gas Chromatography",
A. Bevenue, et al., J. Chromatogr. 1968. 36(4), 529-31; Chem. Abs.
69, 105285z (1968).
(70) "Stabilized Pesticide Compositions", Plant Products Corp. U. S.
3,393.990. July 23, 1968; Chem. Abs. 69, 105336s (1968).
(71) "Qualitative Analysis of Synthetic Organic Pesticides by Spot Tests",
M. Kanda, et al., Nippon Hoigaku Zasshi 1968. 22(3), 229-51 (Japan);
Chem. Abs. 22, 65726x (1970).
(72) "Degradability of Captan and Phaltan", A. Polizu, An. Inst. Cercet.
Prot. Plant., Acad. Stiinte Agr. Silvice 1968. (Pub. 1970), 6, 495-9;
Chem. Abs. 75, 19126r (1971).
1969
(73) "Detection of Captan Residues in Prune Fruits and Blossoms by Thin-
Layer Chromatography, T. E. Archer, et al., Bull. Environ. Contain.
Toxicol. 1969. 4(1), 55-63; Chem. Abs. 22, 86354y (1969).
(74) "Gas-Liquid Chromatography of Pesticides on OV-17 Stationary Phase",
V. Leoni, et al., J. Chromatogr. 1969. 43(3), 388-91; Chem. Abs.
71, 116424m (1969).
(75) "Sprayable Biocides", VEB Farbenfabrik Wolf en FR. 1.569.126. May 30, 1969;
Chem. Abs. 72, 30590w (1970).
(76) "Fusion of Captan (N-(Trichloromethylthio)-4-Cyclohexene-l,2-
Dicarboximide) With Resorcinol", I. B. Pomerantz, et al.,
Tetrahedron Lett. 1969. (60), 5307-10 (Eng); Chem. Abs. 22,
78928q (1970).
1970
(77) "GLC (Gas-Liquid Chromatographic) Retention Times of Pesticides and
Metabolites Containing Phosphorus and Sulfur on Four Thermally Stable
Columns", M. C. Bowman, et al., J. Ass. Offic. Anal. Chem. 1970. 53(3),
499-508; Chem. Abs. 73, 24l79y (1970).
1969
(78) "Analysis of Chlorinated and Organic Phosphorus Pesticides by Gas
Chromatography", M. Kanda, et al., Nippon Hoigaku Zasshi .1969,
23(6), 477-86; Chem. Abs. 73, 65310c (1970).
52
-------
1970
(79) "Extraction, Cleanup, and Gas-Liquid Chromatographic Method for the
Analysis of Captan, Folpet, and Difolatan in Crops", I. H. Pomerantz,
At al., J. Ass. Offic. Anal. Chem. 1970. 53(1), 154-7 (Eng); Chem.
Abs. 22, 7784lu (1970).
(80) "Spectrophotometric Determination of N-(Trichloromethyl)thio)-4-
Cyclohexene-l,2-Dicarboximide(Captan) in Formulations With Mercuric
Thiocyanate", K. Suzuki, et al., Bunseki Kagaku 1970. 19(2),
231-5; Chem. Abs. 72, 131379q (1970).
(81) "Reactions of Certain Trichloromethyl Sulfenyl Fungicides With
Low-Molecular-Weight Ihiols", M. R. Siegel, J. Agr. Food Chem. 1970.
18(5), 819-22 (Eng.); Chem. Abs. 73, 88140m (1970).
(82) "Rapid Method for the Detection and Determination of Captan0,
K. Visweswariah, et al., Anal. Chim. Acta 1970. 52(3), 559-6;
Chem. Abs. 74, 4l368x (1971).
(83) "Systematic Identification and Determination of Pesticides0,
K. Suzuki, et al., Noyaku Kensasko Hokoku 1970. No. 10, 19-23;
Chem. Abs. 74, 139895s (1971).
(84) "Systematic Identification and Determination of Pesticides. 2.
Lower Limits of Detection of Pesticides on Thin Layer Plates",
K. Suzuki, et al., Noyaku Kensasho Hokoku 1970. No. 10, 24-31;
Chem. Abs. 75 , 4461x (1971).
1971
(85) "Collaborative Study of Gas Chromatographic Method for Determining
Captan in Formulations", A. Carlstrom, J. Ass. Offic. Anal. Chem.
1971. 54(3), 688-96; Chem. Abs. 75, 18740z (1971).
(86) "Degradation of Pesticide Residues on Fruits Subjected to Controlled
Pesticide Treatment", M. Riva, et al., Ind. Conserve 1971. 46(2), 85-92;
Chem. Abs. 75, 150428h (1971).
(87) "Routine Estimation of Captan on Individual Sorghum Seeds", P. W. Simon,
et al., J. Ass. Offic. Anal. Chem. 1971. 54(5), 1110-12; Chem. Abs.
76, 754t (1972).
(88) "Decomposition of Fungicides of Phthalimide Type in Wines", K. Soos,
Elelmiszervizsgalati Kozlem, 1971. 17(1-2), 37-9; Chem. Abs.
38833j (1972).
53
-------
(89) "Qualitative Tests for the Detection of Certain Commonly Used
Organochlorine Insecticides", K. Visweswariah, et al., J. Food Sci.
Technol. 1971, 8(2), 77-9; Chem. Abs. 76, 108999r (1972).
(90) "Detection and Quantitative Determination of Certain Chlorinated
Pesticides by Micro-Thin-Layer Chromatography", R. Visweswariah,
et al., J. Chromatogr, 1971. 62(3), 479-84 (Eng); Chem. Abs.
26, 109006b (1972).
(91) "Electrolytic Conductivity Detection of Some Nitrogen-Containing
Herbicides", W. P. Cochrane, et al., J. Chromatogr, 1971. 63(2),
364-9 (Eng); Chem. Abs. §6, 122725e (1972).
1972
(92) "Isolation and Identification of a New Heteroring System. Fusion
of Captan (N-(Trichloromethylthio)-4-Cyclohexene-l,2-Dicarboximide)
WithResorcinol to dive (1,2) Benzoxathiolo(2,)-b) (1,2) Benzoxathiole-
6-Slv-3,9-Diol", I. H. Pomerantz, et al., Tetrahedron 1972, 28(2),
2183-93; Chem. Abs. .77, 19558z (1972).
(93) "Determination of Fhthalimide Pesticide Residues in Wine", L. Biro,
Nehezvegyip. Kut. Intez. Kozlem. 1972. 4, 123-30; Chem. Abs. 77.
112550a (1972).
(94) "Field Test for the Detection and Semiquantitative Estimation of Captan
(N-Trichloromethylthiotetrahydrophthalimide", K. Visweswariah,
et al., Mierochem. J. 1972. 17(4), 396-402; Chem. Abs. 21, 122875z (1972),
(95) "Infrared Analysis of Pesticide Formulations", S. W. Goza, J. Ass.
Off. Anal. Chem. 1972. 55(5), 913-17 (Eng); Chem. Abs. 77, 160898s (1972),
(96) "Preparation of the Fungicides Captan and Phaltan in the Laboratory
and on a Small Industrial Scale", G. Pfeifer, et al., Nehezwegyip.
Kut. Intez. Kozlem, 1972 , 4, 33-8; Chem. Abs. 77, 164369t (1972).
54
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CARBOFURAN
1964
(1) "N-Methylcarbamates", A.-G.B. Farbenfabriken, Neth. Appl. 6,407,316,
Dec. 29, 1964; Chem. Abs. 63, 583a(1965).
(2) "N-Methylcarbamic Esters as Insecticides and Ascaricides", A.-G.B.
Farbenfabriken, Belg. 649,260, Dec. 15, 1964; Chem.Abs. 64,14170g (1%6).
1965
(3) "New Pesticides, FMC Corp., Neth. 6,500,340, July 26, 1965. Correspondes
to U. S. Patents 3,474,170 and 3,474,171 FMC Corporation, Oct. 21, 1969;
Chem. Abs. 64, 3484f (1966).
(4) "Synthesis and Properties of Hydroxybenzofurans. III. Chromatographic
Separation of Hydroxybenzofurans", Kh. Ya. Kipper, Tr. Tallinsk.
Politekhn. Inst., Ser. A No. 230, 77-86(1965); Chem. Abs. 66.,- 10805t
(1967).
1966
(5) "2,3-Dihydro-2,2-Dimethyl-7-Benzofuranyl Methylcarbamate", Neth. Appl.
6,601,012, August 5, 1966, U.S. Appl. Feb. 4, 1965; Chem. Abs. 65,
18560e (1966).
(6) "2,3-Dihydro-2,2-Dimethyl-7-Benzofuranol", FMC Corp. Neth. Appl.
6,602,601, Sept. 2, 1966; U.S. Appl. March 1, 1965; Chem. Abs. 66,
46319b (1967).
1967
(7) "Spectrophotofluorescent and Spectrophotophosphorescent Data on
Insecticidal Carbamates and the Analysis of Five Carbamates in Milk
by Spectrophotofluorometry", C. Bowman, et al., Residue Rev. 17. 23-34
(1967); Chem. Abs. 67_, 20662d (1967).
(8) "Determination of Niagara NIA-10242 and its Phenol Degradation Product
in Corn Silage and Milk and Determination of Other Carbamates by GLC",
M. C. Bowman, et al., J. Ass. Offic. Anal. Chem. .50(4) 926-33(1967);
Chem. Abs. .67, 72517e (1967).
(9) "Synthesis of 2,3-Dihydro-2,2-Dimethyl-7-Benzofuranyl N-Methylcarbamate11,
FMC Corp. U.S. 3,356,690, Dec. 6, 1967; Chem. Abs. 68, 104964n (1968).
1968
*10) "Rapid Procedure for the Chloroacetylation of Microgram Quantities of
Phenols and Detection by Electron-Capture Gas Chromatography", J.
Argauer, et al., Anal. Chem. 40(1), 122-4(1968); Chem. Abs. 68, 46034w
(1968).
"2,3-Dihydro-2,2-Dimethyl-7-Methoxybenzofuran8 and 2,3-Dihydro-2,2-
Dimethyl-7-Benzofuranols", Fisons Pest Control Ltd., S. African
67,05,116, May 10, 1968; Chem. Abs. TO, 87555b (1969).
55
-------
(12) "2,3-Dihydro-2,2-Dimethyl-7-Benzofuranol", FMC Corp., U.S. 3,419,579,
Dec. 1968; Chem.Abs. 70, 68119w (1%9).
1970
(13) "Pesticidal 2,3-Dihydro-2,2-Dimethyl-7-Benzofuranyl Dimethylamino-
carbamates", FMC Corp., U.S. 3,547,955, Dec. 15, 1970; Chem. Abs.
75, 5678k (1971).
1971
(14) "Benzofuran Carbamates for Controlling Arthropods and Nematodes",
FMC Corp. U.S. 3,564,605, Feb. 16, 1971; Chem. Abs. .75, 20175n
(1971).
(15) "Executing Exothermal Addition Reactions", FMC Corp. Ger. Offen.
2,037,694, May 6, 1971; Chem. Abs. 75, 48893u (1971).
(16) "Determination of Residues of Carbofuran and its Toxic Metabolites
by Electron-Capture Gas Chromatography AfterDerivative Formation",
L. I. Butler, et al., J. Ass. Offic. Anal. Chem. 1971. 54(6),
1357-60; Chem. Abs. 76, 69021u (1972).
1972
(17) "N-Perfluoroacyl Derivatives for Methylcarbamate Analysis by Gas
Chromatography", J. N. Seiber, J. Agr. Food Chem. 1972. 20(2),
443-6; Chem. Abs. 77, 1631h (1972).
(18) "Fluorigenic Labeling of Carbamates using Dansyl Chloride. II.
Fluorescence Phenomena of the Derivatives", J. F. Lawrence, J. Chromatogr.
1972. 66(1), 93-9; Chem. Abs. 77, 30115y (1972).
56
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CHLORPYRIFOS
1964
1. "Phosphorylated Pyridine Derivatives", Dow Chemical Co., French
Patent 1,360,901, May 15, 1964 (Equivalent of U. S. 3,244,566
(1966); Chem. Abs. 61, 16052b (1964).
1965
2. "Laboratory Tests with Dursban Insecticide", E. E. Kenaga, et al.,
J. Econ. Entomol, 58(6), 1043-50(1965); Chem. Abs._6A, 1290b (1966).
1966
3. "Synthesis and Insecticidal Activity of Some 0,0-Dialkyl 0-3,5,6-
Trihalo-2-Pyridyl Phosphates and Phosphorothioates" R. H. Rigterink,
et al., J. Agr. Food Chem. 14(3), 304-6 (1966); Chem. Abs. 65,
681e (1966).
4. "Basic Studies on Dursban Insecticide", N. Smith, Down Earth 22(2),
3-7 (1966); Chem. Abs. 65, 17629b (1966).
5. "A Summary of Chemical and Physical Properties of Dursban", H. F.
Brust, Down Earth 22(3), 21-2(1966); Chem. Abs. 66, 68865d (1967).
6. "Vapor Phase Production of 2-Chloropyridine and 2,6-Dichloropyridine",
Dow Chemical Co., U. S. Patent 3,251,848, May 17, 1966; Chem. Abs.
65, 2231h (1966).
1967
7. "Catalytic Hydrolysis of Some Organic Phosphate Pesticides by Copper(II)"
M. M. Mortland, et al., J. Agr. Food Chem. 15(1), 163-7(1967); Chem.
Abs. 66, 54479u (1967).
8. "Use of Paper Partition and Thin-Layer Chromatography for Identification
of Active Ingredient in Dursban Insecticide and its Possible Metabolites",
G. N. Smith, et al., J. Agr. Food Chem. 15(1), 182-6(1967); Chem. Abs.,
54500u (1967).
9. "Determination of Dursban and its Oxygen Analog in Corn and Grass by
Gas Chromatography with Flame Photometric Detection", M. C. Bowman,
et al., J. Agr. Food Chem., 15(4), 651-3(1967); Chem. Abs.67, 72508c (1967)
10. "Analysis of Dursban in Livestock Dips and Sprays", F. P. Czech;
J. Ass. Offie. Anal. Chem. 50(4), 861b-868b(1967); Chem. Abs. 67,
72758J (1967).
57
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11. "Direct Fluorescent Detection of Organothiophosphorus Pesticides and
Some of Their Sulfur-Containing Breakdown Products After Thin-Layer
Chromatography", M. T. H. Ragab, J. Ass. Offic. Anal. Chem. 50(5),
1088-98(1967); Chem. Abs. 67, 99116 (1967).
12. "Temperature-Programmed Gas Chromatography of 20 Phosphorus-
Containing Insecticides on 4 Different Columns and its Application
to the Analysis of Milk and Corn Silage", M. C. Bowman, J. Ass.
Offic. Anal. Chem. 50(6), 1228-36(1967); Chem. Abs. 68, 38221q
(1968).
13. "Monohalopyridinols" Dow Chemical Co., U. S. Patent 3,355,456,
Nov. 28, 1967; Chem. Abs. 68, 29602n (1968).
1968
14. "Determination of 0,0-Dimethyl 0-3,5,6-Trichloro-2-Pyridyl Phos-
phorothioate in Water and Wilt by Gas Chromatography", J. R. Rice
et al., J. Agr. Food Chem. 1968, 16(5), 867-9; Chem. Abs. 69,
75848r (1968).
15. "Rapid Analysis of Halogenated Organic Insecticides in Aqueous
Animal Dips, Using Sodium Biphenyl", F. P. Czech, J. Ass. Offic.
Anal. Chem. 1968, 51(3), 568-72; Chem. Abs. 69, 9898f (1968).
16. "Dursban Determination in Milk and Body Tissues of Cattle", H. V.
Claborn, et al., J. Ass. Offic. Anal. Chem. 1968, 51(6) 1243-5;
Chem. Abs. 70, 10387r (1969).
17. "Ultraviolet Light Decomposition Studies with Dursban (0,0-Diethyl
0-3,5,6-Trichloro-2-Pyridyl Phosphorothioate) and 3,5ff6-Trichloro-2-
Pyridinol", G. N. Smith, J. Econ. Entomol. 1968, 61(3), 793-9;
Chem. Abs. .69, 34964g (1968).
18. "Nuclear Magnetic Resonance Studies of Phosphorus(V) Pesticides",
H. Babad et al., Anal. Chim. Acta 41(2), 259-68(1968); Chem.
Abs. 77181w (1968).
1969
19. "Gas Chromatographic Method for Analysis of 0,0-Diethyl 0-3,5,6-
Trichloro-2-Pyridyl Phosphorothioate (Dursban)11, L. M. Hunt, et al.,
J. Agr. Food Chem. 1969, 17(6), 1166-7; Chem. Abs. 72, 11585g (1970),
20. "Pesticide Residues. Recovery of 65 Organophosphorus Pesticides
from Florisil with a New Solvent-Elution System", H. Beckmann,
J. Ass. Offic. Anal. Chem. 1969, 52(2), 286-93; Chem. Abs. 70,
86520z (1969).
58
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21. "Gas Chromatography of Organophosphorus Pesticides:Retention Times
and Response Data on Three Columns", R. Watts, et al., J. Ass. Offie.
Anal. Chem. 1969, 52(3), 513-21; Chem. Abs. 71, 12019s (1969).
22. "Gas-Liquid Chromatography of Pesticides on OV-17 Stationary Phase",
V. Leoni, et al., J. Chromatogr. 1969, 43(3), 388-91; Chem. Abs.
n, 116424m (1969).
23. "Chromatographic Determination of Trace Amounts of Pesticide Residues",
M. Beroza, et al., Trace Subst. Environ. Health-3, Proc. Univ. Mo.
Annu. Conf., 3rd 1969, 331-51; Chem. Abs. __, 2963t (1969).
24. "Pesticide Residues. XIX. Determining Pesticide Residues in Natural
Waters. I. General Analytical Methods", R. Mestres, et al., Ann.
Fals. Expert. Chim. 1969, 62(685), 75-85; Chem. Abs. 73, 34091c
(1970).
25. "Polycholorinated Aromatic Heterocyclic Nitrogen Compounds'.', Dow
Chemical Co., U. S. Patent 3,420*833, Jan. 7, 1969; Chem. Abs.
71, 3279z (1969).
1970
26. "Determination of Dursban Insecticide in Water, Mud, Vegetation, Fish,
Ducks, Insects, and Crustacea", M. E. Duesch, et al., J. Agr. Food
Chem. 1970, 18(1), 178-9; Chem. Abs. 72,65722t (1970).
27. "GLC (Gas-Liquid Chromatographic) Retention Times of Pesticides and
Metabolites Containing Phosphorus and Sulfur on Four Thermally Stable
Columns", M. C. Bowman, et al., J. Ass. Offie. Anal. Chem. 1970, 53(3),
499-508; Chem. Abs. 73, 24179y (1970).
28. "Improved Extraction Technique for the Infrared Spectrophotometric
Analysis of Dioxathion, Malathion, and Other Organophosphate
Insecticides in Livestock Emulsion Dips", F. P. Czech, et al., J.
Ass. Offic. Anal. Chem. 1970, 53(6), 1160-5; Chem. Abs. 24, 2955s (1971),
29. "Detection, Separation, and Quantitative Recovery of Thirteen Organo-
ffhosphorus Pesticides in Silica Gel GF254» Thin-Layer Chromatograms*,
D. C. Villeneuve, et al., J. Chromatogr. 1970, 48(3), 567-71; Chem.
Abs. 73,54922c (1970).
30. "Proton Magnetic Resonance Studies on Organophosphorus Pesticides. I.
Doubling of Resonances Induced by Asymmetry", Z. L. F. Gaibel, et al.,
Va. J. Sci. 1970, 21(1), 14-16; Chem. Abs. 73, 71883h (1970).
31. "Correlations Between Phosphorus-31 NMR Chemical Shifts and Structures
of Some Organophosphorus Pesticides", R. T. Ross, et.al., Anal. Chim.
Acta 1970, 52(1), 139-41; Chem. Abs. 74, 3100g (1971).
59
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1971
32. "Recovery of Organophosphorus Compounds Using the AOAC Multiresidue
Method", J. R. Pardue, J. Ass. Offic. Anal. Chem. 1971, 54(2) 359-60;
Chem. Abs. 74, 110754J (1971).
33. "Method for Confirmation of Organophosphorus Compounds at the Residue
Level", M. T. Shafk, et al., Bull. Environ. Contain. Toxicol. 1971,6(1),
55-66; Chem. Abs. 74, 124014e (1971).
34. "Thin-Layer Chromatographic Analysis of Organophosphate Pesticides in
the Study of Environmental Contamination (Italian Surface Waters)",
V. Leoni, et al., Farmaco, Ed. Prat. 1971, 26(7), 383-93; Chem. Abs.
25, 128757t (1971).
35. "Esterse Inhibition Technique for the Detection of Organophosphorus
Pesticides on Thin-Layer Chromatograms", T. Stijve, et al., Mitt.
Geb. Lebensmittelunters.Hyg. 1971, 62(1), 25-31; Chem. Abs. 21 (1971).
36. "Sensitivity of Biological and Thin-Layer Chromatographic Determination
of Pesticides", G. M. Abelentseva, et al., Tr. Vses. Soveshch. Issled.
Ostatkov Pestits. Profilakt. Zagryazneniya Prod. Pitan., Kormov Vnesh.
Sredy, 2nd 1971, 331-4; Chem. Abs. 78, 53834s (1973).
37. "Fungicidal 2,6-dichlorpyridine", Dow Chemical Co., U. S. Patent
3,557,124, Jan. 19, 1971; Chem. Abs. 2£,141552w (1971).
1972
38. "Gas Chromatographic Method for Analysis of Chlorpyrifos and Endosulfan
Insecticides in Topically Treated Houseflies", S. Uk, et al., J. Agr.
Food Chem. 1972, 20(3), 638-42; Chem. Abs. 77, 44155y (1972).
39. "Residues of Chlorpyrifos Insecticide in Various Crops..!. Sweep
Codistillation Method for Extraction and Cleanup", P. Maini, et al.,
J. Ass. Off. Anal. Chem. 1972, 55(6), 1265-9; Chem. Abs. 2§, 25089J
(1973).
40. "Invrared Study of the Tautomerism of Chlorinated 2-Pyridinols Isolated
in an Argon Matrix", S. T. King, et al., Tetrahedron 1972, 28(24),
5859-63; Chem. Abs. 2§. 110077y (1973).
41. "Metallofluorescent Indicators as Spray Reagents for the in situ
Determination of Organophosphorus Pesticides on Thin-Layer Chromatograms",
T. F. Bidleman, et al., Anal. Chim. Acta 1972, 60(1), 13-23; Chem.
Abs. 77, 84271q (1972).
42. "Determination of Diazinon and Dursban in Animal Milk, Organs, and
Tissues Using Gas Chromatography", G. A. Talanov, et al., Khim Sel.
Khoz., 1972, 10(11), 842-4; Chem. Abs. 78, 39096w (1973).
60
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43. "2-Pyridinol Phosphates", Kumiai Chemical Industry Co., Ltd., U. S.
Patent 3,686,191, Aug. 22, 1972; Chem. Abs. 77, 151983p (1972).
44. "Organic Phosphates", Kumiai Chemical Industry Co., Ltd., Japan. Kokai
72 16,469, Sept. 1, 1972; Chem. Abs. 2Z> 151944b (1972).
1973
45. "Conditioning of Polyalkyl Glycol Liquid Phases for Flame Photometric
Gas Chromatographic Analysis of Dursban and itsOxygen Analog", :
D. L. Struble, J. Ass. Off. Anal. Chem. 1973, 56(1), 49-52; Chem.
Abs. 78, 68014y (1973).
46. "Detection of Organophosphorus Pesticides by in situ Fluorometry on
Thin-Layer Chromatograms", G. L. Brun, et al., J. Chromatogr. 1973,
80(1), 117-23; Chem. Abs. 29, 112253x (1973).
61
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CIODRIN
1961
1. "Aryl Phosphate Compounds", Shell Oil Co., U. S. Patent 2,982,685,
May 2, 1961; Chem. Abs. 55, 22240b,(1961).
2. "Aryl Phosphate Compounds", Shell Oil Co., U. S. Patent 2,982,686,
May 2, 1961; Chem. Abs. 55, 22240d (1961)
1964
3. "Synthesis of a-Methylbenzyl 3-Dimethoxyphosphinyloxy Crotonate
Labeled with Phosphorus-32 and Carbon-14", J. C. Potter et al.,
J. Agr. Food Chem., 12(5) 439-42(1964); Chem. Abs. 61, 13181c (1964).
4. "Analysis of Insecticides in Aqueous Emulsions used in Livestock Dips
and Sprays: General Infrared Method", F. P. Szech, J. Assoc. Office.
Agr. Cehmists 47(5), 829-37(1964); Chem. Abs. 61, 15283 (1964).
5. "Thin-Layer Cheomatography of Organophosphorus Pesticides and Acids
on Microcheomatoplates", C. W. Stanley, J. Chromatog. 16(3), 467-75
(1964); Chem. Abs. 62, 11090a (1964).
1965
6. "Simultaneous and Selective Detection of Phosphorus Sulfur, and -Halogen
in Pesticides by Microcoulometric Gas Chromatography", H. P. Burchfield
et al., J. Agr. Food Chem. 13(6), 511-16(1965); Chem. Abs. 64, 4193b
(1966).
7. "Determination of Organophosphorus Insecticide Residues Using the
Emission Spectrometric Detector", C. A. Bache et al., Anal. Chem.
37(13) 1477-80(1965); Chem. Abs. 64, 1288a (1966).
8. "Identification of Trace Amounts of Organophosphorus Pesticides of
Frustrated Multiple Internal Reflectance Spectroscopy", T. S. Hermann,
Appl. Spectry. 19(1), 10-14(1965); Chem. Abs. 62, 12387b (1965).
1967
9. "Detector Cell for- Measuring Picogram Quantities of Organophosphorus
Insecticides, Prethrin Synergists, and Other Compounds by Gas
Chromatography", W. N. Bruce, J. Agr. Food Chem. 15(1), 178-81(1967);
Chem. Abs. 66, 54499a (1967).
10. "Ciodrin Insecticide", P. E. Porter, Anal. Methods Pestic. Plant
Growth Regul. Food Additivies 1967, 5, 243-56; Chem. Abs. 70*
76685 (1969).
62
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11. "Direct Fluorescent Detection of Organothiophosphorus Pesticides and
Some of Their Sulfur-Containing Breakdown Products After Thin-Layer
Chromatography", T. H. Ragab, J. Ass. Offic. Anal. Chem. 50(5), 1088-
98(1967); Chem. Abs. 67, 99116, (1967).
12. "Thin-Layer Chromatographic Separation Scheme for Insecticidally
Active Phosphoric Acid Esters", J. A. Guth, Pflanzenschutzberichte,
25(9-10), 129-43(1967); Chem. Abs. 67, 72784q (1967).
1968
13. "Organophosphorus Insecticide Degradation by Heat-Labile Substances
in Soil", L. W. Getzin et al., J. Agr. Food Chem. 1968, 16(4) 598-601;
Chem. Abs. 69, 85694 (1968).
14. "High-Resolution N.M.R. Spectra of Pesticides. I. Organophosphorus
Pesticides", L. H. Keith et al., J. Ass. Offic. Anal. Chem. 1968,
51(5), 1063-94; Chem. Abs. 69, 75849s (1968).
15. "Versatility of OV-17 Substrate for Gas Chromatography of Pesticides",
C. A. Basche et al., J. Ass. Offic. Anal. Chem. 1968, 51(6), 1270-1;
Chem. Abs. 22, 27907h (1969).
16. "Nuclear Magnetic Resonance Studies of Phosphorus(V) Pesticides. I.
Chemical Shifts of Protons as a Means of Identification of Pesticides",
H. Babad et al., Anal. Chem. Acta 41(2), 259-68(1968); Chem. Abs. 68,
77181w (1968).
17. "Thin-Layer Chromatographic Determination of Ciodrin in Milk and Meat",
N. I. Ryazhenov, Tr., Vses. Nauch.-Issled. Inst. Vet. Sanit. 1968,
31, 315-18; Chem. Abs. 71, 100514e (1969).
18. "Degradation in Soils of Ciodrin, an Organophosphate Insecticide",
J. G. Konrad et al., J. Agr. Food Chem. 1969, 17(2), 226-30; Chem.
Abs. 70, 114121r, (1969).
1969
19. "Conversion of the Insecticide, Ciodrin to Acetophenone for Micro-
determination", A. Westlake et al., J. Agr. Food Chem. 1969, 17(6),
1157-9; Chem. Abs. 72, 2462n (1970).
20. "Determination of Ciodrin From Fortified Animal Tissues by Oscillo-
polarography of its Conversion Product, Acetophenone", A. Westlake
et al., J. Agr. Food Chem. 1969, 17(6), 1160-3; Chem. Abs. 72,
20635a (1970).
21. "Gas Chromatography of Organophosphorus Pesticides:Retention Times and
Response Data on Three Columns", R. R. Watts et al., J. Ass. Offic.
Anal. Chem. 1969, 52(3), 513-21; Chem. Abs. 71, 12019s (1969).
22. "Charcoal Column Cleanup Method for Many Organophosphorus Pesticide
Residues in Crop Extracts", R. R. Watts et al., J. Ass. Offic. Anal.
Chem. 1969, 52(3), 522-6; Chem. Abs. 21* 21124z (1969).
63
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23. "Dialkyl Phosphinyloxy-3-Butenoates Isoenolphosphates", Shell International
Research Maatschappij N.V., Ger. Offen. 1,920,672, Nov. 1969; Chem. Abs
22, 4311w (1970).
1970
24. "GLC [Gas-Liquid Chromatographic] Retention Times of Pesticides and
Metabolites Containing Phosphorus and Sulfur on Four Thermally Stable
Columns", M. C. Bowman, et al., J. Ass. Offic. Anal. Chem. 1970, 53(3),
499-508; Chem. Abs. 73t 24179y (1970).
25. "Determination of Crotoxyphos in Milk and in the Body Tissues of Cattle
and Pigs", D. D. Oehler et al., J. Ass. Offic. Anal. Chem. 1970,
53(5), 1045-7; Chem. Abs. 73, 108391z (1970).
26. "Correlations Between Phosphorus-31 NMR Chemical Shifts and Structures
of Some Organophosphorus Pesticides", R. T. Ross et al., Anal. Chim.
Acts, 1970, 52(1), 139-41; Chem. Abs. 74, 31000g (1971).
27. "Enzymic Agar-Diffusion Method for Detecting Organophosphorus Insecticide
Residues in Products of Animal Origin", A. A. Nepoklonov et al., Tr.
Vses. Nauch.-Issled. Inst. Vet. Sanit., 1970, 35, 383-90; Chem. Abs.
26, 122722b (1972).
1971
28. "Enzyme-Colorimetric Method of Determining Chlorophos. Dibrom. Ruelene,
Ruelene, Ciodrin, Sevin, and Dicresyl N-Methylcarbamate in Milk and
Meat", G. A. Talanov et al., Tr. Vses. Sovesch. Issled. Ostatkov Pestits,
Profil. Zagryaz. Inst. Prod. Pitan., Kormov Vnesh. Sredy, 2nd 1970
(Pub. 1971), 318-20; Chem. Abs. 79, 135387h (1973).
29. "Determination of Ciodrin Residues in Milk by Paper Chromatography",
V. V. Petrovskiu et al., Tr. Vses. Soveshch, issued, Ostatkov Pestits.
Profil. Zugryaz. Imi., Prod, Pitan., Kormov-Vnesh. Sredy. 2nd 1970
(Pub. 1971), 358-9J; Chem. Abs. 79, 135393g (1973).
64
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DEMETON
1935
(1) "Addition of Hydrogen Sulfide and Hercaptans to Alkylene Oxides",
C. D. Nenitsescu, et al., Ber. 68B, 587-91 (1935); Chem. Abs. 29,
3979 1 (1935).
1946
(2) "Dehydration of Hydroxyalkyl Sulfides", Union Oil Co. of California,
U. S. 2.402.878. June 25, 1946; Chem. Abs. 40, 6496 7 (1946).
1949
(3) "Reactions of Ethylene Oxides. II. Reactions with thio amides,
thiols, and inorganic sulfur salts", C. C. J. Culvenor, et al.,
J. Chem. Soc., 1949. 278-82; Chem. Abs. 43, 7420e (1949).
1953
(4) "Determination of Isomers of 0,0-Diethyl Ethylthioethyl Thiophos-
phate", K. Gardner, et al., Anal. Chem. 25, 1849-53 (1953); Chem.
Abs. 48, 2975a (1954).
(5) "The Separation of Systox Chemicals by Paper Chromatography", H.
Koike, Oyo-Kontyu 2t 77-8 (1953); Chem. Abs. 48_, 3618b (1954).
1954
(6) "Analysis of Systemic Insecticides", P. A. Giang, J. Assoc. Offie.
Agr. Chemists JJ7, 642-7 (1954); Chem. Abs. 48, 10982f (1954).
(7) "Determination of Insecticides by Enzymic Methods", J. W. Cook,
J Assoc. Offic. Agr. Chemists 37. 561-4 (1954); Chem. Abs. 48,
10988f (1954).
(8) "Paper Chromatography of the Systemic Insecticides, Demeton and
Schradan", R. B. March, et al., J. Agr. Food Chem. 2, 732-5 (1954);
Chem. Abs. 48, 14094a (1954). ~~
(9) "Paper Chromatography of Some Organic Phosphate Insecticides. I. New
Spot Test", J. W. Cook, J. Assoc. Offic. Agr. Chemists 37, 984-7
(1954); Pesticides JL5A, 2665b (1955).
(10) "Isomerization of B-Ethylmercaptoethyl Diethyl Thionophosphate (Systox)",
T. R. Fukuto, et al., J. Am. Chem. Soc. 76, 5103-6 (1954): Chem. Abs.
49, 12271f (1955). —
1955
(11) "A Review of Systox", R. Von Rumker, Agr. Chemicals 10. No. 1, 47-8,
122-23 (1955); Chem. Abs. 49, 6531a (1955).
65
-------
1955
(12) "Detection of Dlethyl 2-Ethylthioethyl Thionophosphoric Acid", K,
Grosskopf, U.S. 2,709,127, May 24, 1955: Chem. Abs, 49, 14586b (1955).
(13) "Inter-Relations Between Basic and Applied Research In the Develop-
ment of Modern Pesticides", R. von Rumker, Agr. Chemicals 10, No.
12, 40-2, 103, 105, 107 (1955); Chem. Abs, 50, 3700'g (1956).
1956
(14) "Rapid Analysis of Reaction Mixtures by Nuclear Magnetic Resonance
(NMR) Spectroscopy", N. Muller, et al.t J. Am, Chem. Soc. 78, 5182-
3 (1956); Chem. Abs. 51, 3285b (1957).
(15) "Organic Phosphorus-Containing Insecticides. II. Enzymic Determin-
ation of Small Amounts in the Air", J. Janok, et al., Pracovni
Lekarstvi JJ, 296-8 (1956); Chem. Abs. 51, 5350c (1957).
1957
(16) "Hydroxy Thioethers", Union Oil Co. of California, U.S, 2,776,997,
Jan. 8, 1967; Chem. Abs. 51, 8780c (1957).
(17) "Mercaptophos and its Analogs", U.S.S.R. 105.444j Apr. 25, 1957;
Chem. Abs. 51, 14784i (1957).
(18) "Determination of Diethyl Thionophosphoric Acid Ester of 2-Hydroxy-
ethylthioethyl Ether", DrHgerwerk, Heinrich & Bernh. Drager. Ger.
1,006,629, Apr. 18, 1957; Chem. Abs. 54, 176c (1960).
1958
(19) "Analysis of Mixtures of Isomers of Demeton", K. Groves, J. Agr. Food
Chem. .6, 30-1 (1958); Chem. Abs. _52, 7607g (1958).
(20) "Analysis of Systox", M. Vancea, et al., Acad. rep. populare Romine,
Filiala Cluj, Studii cercetari chim. S>, 171-6 (1958); Chem. Abs. .55
8744a (1961).
1959
(21) "Identification and Determination of Systox", K. Grosskopf, Chem.. Ztg,
JJ3, 115-17 (1959); Chem. Abs. .53, 13493f (1959).
(22) "Gas Chromatography of Pesticides", D. M. Coiilson, et al., J, Agr,
Food Chem. 7_, 250-1 (1959); Chem. Abs. 53, 19280d (1959).
(23) "Vibration Spectra of Organophosphorus Compounds. The Problem of the
Characterization of the P:S Frequency", E. M. Popov, et al,, Zhur.
Obshchei Khim. 29, 1996-2006 (1959): Chem. Abs, 54, 8282b (1960).
66
-------
1961
(24) "Organic Phosphorus Compounds. VI. Effects of Structural Variations
in Systox and Isosystox Analogs on Their Reactions with Cholin-
esterase", F. W. Hoffmann* et al., J. Am. Chem. Soc. 83, 706-8
<1961); Chem. Abs. .55, 12280h (1961).
(25) "The Effect of Ultraviolet Light (2537 A) on 141 Pesticide Chem-
icals by Paper Chromatography", L. C. Mitchell, J. Assoc. Offie.
Agr. Chemists 44., 643-712 (1961); Chem. Abs. 56, 3849e. (1962).
(26) "An Agar-Diffusion Method for the Estimation of Organic Phosphate
Insecticides, E. Sandi, et al., Chem. & Ind. (London) 1961, 1161-
2; Chem. Abs. 56, 7749i (1962).
(27) "Phosphate Insecticide", Sandoz Ltd., Ger. 1,116.217, Nov. 2, 1961;
. Chem. Abs. 11447f (1962).
(28) "The Test for Quantitative Determination of Esters of Thiophosphoric
Acid in Biological Material", R. Fischer, et al., Arch. Toxikol. 19,
119-40, (1961); Chem. Abs. 57, 17129c (1962).
(29) "lexicological Detection and Determination of Thiophosphoric Acid
Esters. II", R. Fischer, et al., Pflanzenschutz Ber. 27, 165-76
(1961); Chem. Abs. .57, 5677e (1963).
1962
(30) "Six Phosphate Pesticide Residues in Green Leafy Vegetables. Cleanup
i Method and Paper Chromatographic Identification", M. E. Getz, J.
Assoc. Offic. Agr. Chemists 45, 393-6 (1962); Chem. Abs. .57, 2637h (1962)
(31) "Degradation Esters of Systox, Di-Syston, and Thlmet on Field-
Sprayed Kale", M. E. Getz, J. Assoc. Offic. Agr. Chemists 45, 397-
401 (1962); Chem. Abs. 5>7, 2637i (1962).
(32) "Esters of Thiolphosphoric, Thiolphosphonic and Thiolphosphinic Acids",
Farbenfabriken Bayer A.-G., Ger. 1,124,034. Feb. 22, (1962); Chem. Abs.
.57, 3*85b (1962).
(33) "Application of Oscillographic Polarography to Determination of Organic
Phosphorus Pesticide Residues", R. J. Gajan, J. Assoc. Offic. Agr.
Chemists 45, 401-6 (1962); Chem. Abs. .57., 3821a (1962).
(34) "Butynyl Phosphates", Monsanto Chemical Co., U.S. 3.030.265. Apr. 17,
(1962); Chem. Abs. .57, 8439e (1962).
(35) "Process for the Manufacture of Phosphorus-Containing Esters", Sandoz
Ltd., Basel, Switz., U.S. 3.041.367. June 26, 1962; Chem. Abs. 57,
16399a (1962).
67
-------
1962
(36) "Electrochemical Determination of Organophosphorus Compounds", G. G.
Guilbault, et al., Anal. Chen. 34, 1437-9 (1962); Chem. Abs. 58,
888g (1963).
(37) "Properties of Amides of Acids of Phosphours. I. Reactions of
Phosphorous Amides with Phenols", K. A. Petrov, et al., Ah. Ob-
shch. Khim. ^2_, 920-3 (1962); Chem. Abs. .58, 2391h (1963).
(38) "Diethyl 4-Nitrophenyl Thiophosphate and Diethyl 2-(Ethylthio)-
Ethyl Thiophosphate", U.S.S.R. 144,845, Feb. 26, (1962); Chem. Abs.
.58, 6750a (1963). '
(39) "Separation of Initial, Intermediate, and Final Products in the
Air in the Manufacture of Mercaptophos", M. D. Skanavi, Tr. po
Khim. i Khim. Tekhnol. 1962, No. 1, 151-3; Chem. Abs. _59, 1028a (1963).
(40) "Extinguishing of Fluorescence by Some Organophosphorus Insecticides",
M. A. Trotsenko, Novoe v Oblasti Sanit.-Khim. Analiza (Raboty po
Prom.-Sanit. Khim.) 1962. 175-8; Chem. Abs. .59, 4493f (1963).
(41) "Separation and Determination of Organophosphorus Insecticides in
Vegetable Foods", G. Ya. Isaeva, et al., Vopr. Pitaniya J21, No. 6,
64-7 (1962); Chem. Abs. 59, 14496b (1963).
(42) "Detection and Determination of Phosphate-Ester Insecticides in
Plant Materials", Em. Saudi, et al., Elelmiszervizsgalati Kozle-
meny JJ (1-2), 17-27 (1962); Chem. Abs. 64, 8866b (1966).
1963
(43) "The Detection of Residues of Systox and its Toxic Metabolites in
the Presence of Other Organophosphorus Pesticides", J. M. Adams,
et al., J. Agr. Food Chem. 11, 178-80 (1963); Chem. Abs. 58, 13069a (1963)
(44) "Thin-Layer Chromatography for Insecticide Analysis", K. C. Walker,
et al., J. Assoc. Offic. Agr. Chemists 46, 250-61 (1963); Chem. Abs.
58, 14626g (1963).
(45) "Rodenticidal Esters of Thiolphosphoric Acids", Farbenfabriken Bayer
A.-G., Ger. 1.144.265, Feb. 28, 1963; Chem. Abs. 59, 3778c (1963).
(46) "Phosphoric Acid Esters", Farbenfabriken Bayer A.-G., U.S. 3.082.240,
Mar. 19, 1963; Chem. Abs. 59, 5077g (1963).
(47) "Thiolo- and Selenolo-Phosphoric, -Thionophosphoric, -Phosphonic and
-Thionophosphonic Acid Esters", Farbenfabriken Bayer A.-G., Brit.
922,378, Mar. 27, (1963); Chem. Abs. 59, 10123g (1963).
68
-------
(48) "Detection of Systox and Meta-Systox by Heavy Metal Complex Com-
pounds", M. Geldmacher-Mallinckrodt, et al., Arch. Toxikol. 20.
114-26 (1963); Chem. Abs. 59, 10708b (1963).
(49) "Determination of Xhiophos and Mercaptophos Residues in Foods",
G. Ya. Isaeva, et al., Vopr. Pitaniya .22(3), 88-9 (1963); Chem.
Abs. 59, 12080b (1963).
(50) "Detection of Systox [Demeton] and Meta-Systox as Complexes With
Heavy Metals" M. Geldmacher-Mallinckrodt, Deut. Z. Ges. Gerichtl
Med. 54(1), 9ti(1963); Chem. Abs. 59, 15873e (1963).
(51) "Thin Layer Chromatography of Organic Thiophosphorus Compounds",
T. A. Mastryukova, et al., Izv. Akad. Nauk SSSR, Ser. Khim.
1963(12). 2211-13; Chem. Abs. 60, 9882g (1964).
(52) "Determination of Residues in Plants and Mammals", D. F. Heath,
Radiation Radioisotopes Appl. Insects Agr. Importance, Proc.
Symp., Athens 1963. 185-92; Chem. Abs. 60, 12580g (1964).
(53) "Applications of the Microcoulometric Titrating System as a
Detector in Gas Chromatography of Pesticide Residues", J. A.
Challacombe, et al., Residue Rev. 5, 57-72 (1963); Chem. Abs.
61, 9975h (1964). ""
(54) "Detection of Systox and Meta-Systox by Heavy Metal Complex
Compounds", M. Geldmacher-Mallinckrodt, et al., Arch. Toxikol.
20(2), 114-26 (1963); Bhem. Abs. 62, 6785a (1965).
1964
(55) "Characteristic Infrared Absorption Frequencies of Organophos-
phorus Compounds. I. Phosphoryl (P:0) Group'.', L. C. Thomas,
et al., Spectrochim. Acta K)(3), 467-87 (1964); Chem. Abs. 60,
8783f (1964).
(56) "Preparation of p-Dithiane and Diethyl Sulfide", Phillips
Petroleum Co. U.S. 3.119.838. Jan. 28, 1964; Chem. Abs. 60.
9287g (1964).
(57) "Fluorometric Determination of Lipase, Acylase, «- and Y~
Chymotrypsin and Inhibitors of These Enzymes", G. G. Guilbault,
et al., Anal. Chem. 36(2), 409-12 (1964); Chem. Abs. 60, 10985g
(1964).
(58) "Thiaalkyl Acrylates: The Influence of Sulfur in the Side
Chain", R. M. McCurdy, et al., J. Polymer Sci. Pt. A 2(3),
1185-92 (1964); Chem. Abs. 60, 13326h (1964).
69
-------
(59) "Screening Procedure for Organothiophosphate Pesticide Residues
on Fruits and Vegetables by Microcoulometric Gas Chromatography",
R. C. Nelson, J. Assoc. Offie. Agr. Chemists 47(2), 289-92
(196A); Chem. Abs. 61, 2388c (1964).
(60) "Systox", D. MacDougall, Anal. Methods Pesticides, Plant Growth
Regulators Food Additives (Gunter Zweig, editor. Academic) 2,
451-72 (1964); Chem. Abs. 61, 11264g and 11263e (1964).
(61) "The Determination of Traces of Phosphoric Esters by Oscillo-
graphic Polarography", P. Nangniot, Anal. Chim. Acta 31(2),
166-74 (1964); Chem. Abs. 61, 12563e (1964).
(62) "The Detection of Organophosphorus Pesticides on Thin-Layer
Chromatograms", P. J. Bunyan, Analyst ,89(1062), 615-18 (1964);
Chem. Abs. 61, 15282f (1964).
(63) "Thin-Layer Chromatography for Organothiophosphate Pesticide
Residue Determination", M. F. Koracs, Jr., J. Assoc. Offic.
Agr. Chemists 47(6), 1097-102 (1964); Chem. Abs. 62, 4517h
(1965).
(64) "Thin-Layer Chromatography of Organophosphorus Pesticides and
Acids on Microchromatoplates", C. W. Stanley, J. Chromatog.
.16(3), 467-75 (1964); Chem. Abs. 62, 11090a (1965).
1965
(65) "Identification of Trace Amounts of Organophosphorus Pesticides
by Frustrated Multiple Internal Reflectance Spectroscopy",
T. S. Hermann, Appl. Spectry. .19(1), 10-14 (1965); Chem. Abs. 62,
12387b (1965).
(66) "Detection of Systox-Type Systemic Thiophosphoric Esters and of
Their Oxidized Analogs", H. Ackermann, et al., J. Chromatog.
JJ(3), 608-11 (1965); Chem. Abs. 63, 2334d (1965).
(67) "Electrolytic Conductivity Detector for Gas Chromatography",
D. M. Coulson, Gas Chromatog. 1(4), 134-7 (1965); Chem. Abs.
£3, 6238f (1965).
(68) "An Approach to the Separation, Identification, and Determination
of at Least Ten Organophosphate Pesticide Residues in Raw Agri-
cultural Products", D. F. McCaulley, J. Assoc. Offic. Agr.
Chemists 48(3), 659-65 (1965); Chem. Abs. 63, 7564h (1965).
70
-------
(69) "Determination of Nonaromatic Ihiophosphoric Acid Esters",
W. Kisser, et al., Z. Anal. Chem. 213(5), 349-53 (1965); Chem.
Abs. 63, 17156h (1965).
(70) "Screening Procedure for Organothiophosphate Pesticide Residues
on Fruits and Vegetables Using Microcoulometric Gas Chromato-
graphy", R. C. Nelson, J. Assoc. Offic. Agr. Chemists 48(4).
752-9 (1965); Chem. Abs. 63, 18932d (1965).
(71) "Determination of Organophosphorus Insecticide Residues Using
the Emission Spectrometric Detector", C. A. Bache, et al.,
Anal. Chem. 37(12), 1477-80 (1965); Chem. Abs. 1288a (1966).
(72) "2-(Ethylthio)ethanol", Phillips Petroleum Co. U.S. 3.213.144.
Oct. 19, 1965; Chem. Abs. 64, 4943c (1966).
1966
(73) "Gas Chromatographic Column for Pesticide Residue Analysis:
Retention Times and Response Data", J. A. Burke, et al., J.
Assoc. Offic. Anal. Chemists 49(2), 374-85 (1966); Chem. Abs.
65, 2894g (1966).
(74) "Separation and Detection of Submicrogram Quantities of Pesti-
cides by an Improved TLC Technique", H. Beckman, et al., Bull.
Environ. Contain. Toxicol. 1(3), 78-85 (1966); Chem. Abs. 65.
7894e (1966).
(75) "Determination of Organophosphorus Insecticide Residues Using
Cooke's Emission Spectroscopic Detector", C. A. Bache, et al., 12,
35-44 (1966); Chem. Abs. 7895e (1966).
(76) "Determination of Demeton Residues by Infrared Spectrophotometry",
P. A. Giang, et al., J. Agr. Food Chem., 14(4), 380-3 (1966);
Chem. Abs. 65, 9650d (1966).
(77) "Schoenemann Reaction for the Detection of Thiophosphates",
Kh. Lohs, et al., Z. Chem. 6(6), 224 (1966); Chem. Abs. 65,
11324c (1966).
1967
(78) "Determination of Organophosphorus Residues in Plants. VI.
Detection of Metabolites of Di-Syston by Electron-Capturing
Gas Chromatography", S. Okui, et al., Shokukhin Eiseigaku
Zasshi 8(1), 73-7 (1967); Chem. Abs. 67, 2102If (1967).
71
-------
(79) "Direct Fluorescent Detection of Organothiophosphorus Pesticide6
*nd Some of Their Sulfur-Containing Breakdown Products After
Thin-Layer Chromatograpny", M. T. H. Ragab, J. Aasoc. Offie.
Anal. Chem. 10(5). 1088-98 (1967); Chem. Aba. 67,, 99119p (1967).
1968
(80) "Nuclear Magnetic Resonance Studies of the Phosphorus (V)
Pesticides. II. A Rapid Determination of the Isomer Ratio of
Systox", H. Babad, et al., Anal. Chim. Acta 40(3), 387-92
(1968); Chem. Abs. 68, 67993y (1968).
(81) "Nuclear Magnetic Resonance Studies of Phosphorus (V) Pesticides.
I. Chemical Shifts of Protons as a Means of Identification of
Pesticides", B. Babad, et al., Anal. Chim. Acta££(2), 259-68
(1968); Chem, Abs. 68, 77181* (1968).
(82) "8-Hydroxyalkyl Ethyl Sulfides", Badische Anilin- & Soda-Pabrik
A.-G., Cer. 1.261.501. Peb. 22, 1968; Cheni. Abs. 69., 2512s
(1968).
(83) "Thin-Layer Chromatography of Organophosphorus Insecticides with
Several Adsorbents and Ternary Solvent Systems", M.E. Cetz, et al.,
J. Assoc. Offic. Anal. Cham. 1968. 51(5), 1101-7; Chem. Abs. 6£,
75850k (1968).
(84) "Ethyl P-Hydroxyethyl Tbioethers", Anilin- und Soda-Pabrik
A.-6.) Cer. 1.270.550. June 20, 1968; Chem. Abs. 6£, 86364£
(1968).
(85) "Thin-Layer Chromatographic-Enzymic Detection of Organophos-
phorus Insecticides. Activation of Weak Esterase Inhibitors",
H. Ackermann, J. Chromatogr. 1968. 36(3), 309-17; Chem. Abs.
69, 105284y (1968).
(86) "Determination of Residues of Di-Syeton and Metabolites by
Thermionic Plame Gas Chromatography", J. S. Thornton, at al.,
J. Agr. Pood Chem. 1968. 16(6), 895-8; Chem. Abs. 10, 2682t
(1969).
1969
(87) "Gas-Liquid Chromatographic Determination of Residues of Di-
•ulfoton, Oxydemetoomethyl, and Their Metabolites in Tobacco
Plants", M. C. Bowman, et al., J. Assoc. Offic. Anal. Cham. 1969.
52(1), 157-62; Chem. Abs. 20, 44818x (1969).
72
-------
(88) "Pesticide Residue*. Recovery of 65 Organopho*pboru* Pesticide*
from Florid 1 with a Mew Solvent-Elutloa System", B. Beckmen,
et al., J. Aaaoc. Offlc. Anal. Chen, 1969. 52(2), 266-93; Cbem.
Abe. JO, 86520z (1969).
(89) "Field lonization Spectra of Some Pectlcidal and Other Biologically
Significant Compound*", J. M. Damlco, et al. , Int. J. Mass
Spectrom. Ion Pbyf. 1969. 2(2), 161-82; Cbem. Aba. 22» 105767d
(1969).
(90) "Poiyamide«Layer Chrooatography of Organophoaphoru* Pesticides",
K. Nagacawa, et al., J. Cbromatogr. 1969. 39(3), 282-90; Cbem.
Ab*. 22» Il4093h (1969).
(91) "Gas Chromatography of Organophospborus Pesticides: Retention
Times and Response Data on Three Columns", R. R. Watts, et al.,
J. Assoc. Of fie. Anal. Chem. 1969. 52(3), 513-21; Chem. Abs.
21, 12019s (1969).
(92) "Determination of Organophosphorus Pesticides in Water",
G. Zweig, et al. , Residue Rev. 1969. 26, 17-36; Chem. Abs. 21 »
80107u (1969).
(93) "Evaluation of Esterases from Livers of Beef, Pig, Sheep,
Monkey, and Chicken for Detection of Some Pesticides by Thin-
Layer Chromatographic-Enzyme Inhibition Technique", C. E.
Mendoza, Analyst (London) 1969. 94(1122), 805-10; Chem. Abs.
22, 42125m (1970).
(94) "2-(Ethylthio)ethanol", Phillip* Petroleum Co.. U.S. 3.487.113.
Dec. 30, 1969; Cbem. Abs. ]2, 7 8367 n (1970).
(95) "Chromatographic Determination of Trace Amounts of Pesticide
Residue*", M. Beroza, at al., Trace Subst. Environ. Bealth-3, Proc.
Univ. Mo. Annu. Conf , , 3rd 1969 (Pub. 1970), 331-51; Cbem. Ab*.
24, 2963t (1971).
1970
(96) "Report on Pho*phated Pesticides", K. A. Me Cully, J. Aseoc. Offic.
Anal. Chem. 1970. 53(2), 363-5; Cbem. Ab*. 22, 131144J (1970).
(97) "Polarography of Demeton, Disulfoton, and Phorate", I. J. Graham-
Bryce, Pestle. Sci. 1970. 1(2), 73-4; Chem. Abs. 22, 13441b
(1970).
(98) "CLC [Gas-Liquid Chromatographic] Retention Times of Pesticides
and Metabolites Containing Pho*phoru* and Sulfur on Four
Thermally Stable Column*", M. C. Bowman, et al., J. A**oc. Offic.
Anal. Chem. 1970. 53(3), 499-508; Chem. Ab*. 23, 24l79y (1970).
73
-------
(99) "Routine Determination of Organophosphorus Insecticide Residues
in Vegetables. II. Screening Procedure for Water Soluble In-
secticides", D. J. Sissons, et al., J. Chromatogr. 1970. 48(3),
468-77; Chem. Abs. 73, 75726g (1970).
(100) "Gas-Chromatographic Determination of Pesticides. III.
Determination of Residues of Organophosphorus Pesticides",
I. Takase, et al., Novaku-Seisan Gilutsu 1970. 22, 13-21;
Chem. Abs. .76, 238641 (1972).
1971
(101) "Routine Method for the Determination of Organophosphorus In-
secticides by Thin-Layer Chromatography", 0. Antoine, et al.,
J. Chromatogr. 1971. 58(2), 247-56; Chem. Abs. 75, 75234m
(1971).
(102) "Infrared and Ultraviolet Spectra of Seventy-Six Pesticides",
R. C. Gore, et al., J. Assoc. Offie. Anal. Chem. 1971. 54(5),
1040-82; Chem. Abs. 75, 117202g (1971).
1972
(103) "Metallofluorescent Indicators as Spray Reagents for the in
Situ Determination of Organophosphorus Pesticides on Thin-Layer
Chroma tograms", T. F. Bidleman, et al., Anal. Chim. Acta 1972.
60(1), 13-23; Chem. Abs. 27, 84271q (1972).
(104) "Chemical Hydrolysis of Some Organic Phosphorus and Carbamate
Pesticides in Aquatic Environments", S. D. Faust, et al.,
Environ. Lett. 1972. 3(3), 171-201; Chem. Abs. 27, 110352p
(1972).
(105) "Continuous Manufacture of P-Hydroxydiethyl Sulfide",
Farbenfabriken Bayer A.-G., Ger. Offen. 2.108.902. Aug. 31,
1972; Chem. Abs. 2Z» 139418a (1972).
(106) "Infrared Analysis of Pesticide Formulations", S. W. Goza,
J. Assoc. Offie. Anal. Chem. 1972. 55(5), 913-17; Chem. Abs.
27, 160897r (1972).
74
-------
DIAZINON
1953
(1) "A New Insecticide With a Wide Range of Activity", R. Gasser, Z.
Naturforsch. 8b, 225-32 (1953); Chem. Abs. 47, 10167h (1953).
1954
(2) "Insecticidal Phosphate Esters", J. R. Geigy A.-G., Brit. 713,278
Aug. 11, 1954; Chem. Abs. 50, 1092h (1956).
(3) "Paper Chromatography of Some Organic Phosphate Insecticides. I.
New Spot Test", J. W. Cook, J. Assoc. Offic. Agr. Chemists 37.
984-7 (1954); Chem. Abs. 49, 2665b (1955).
1955
(4) "Chromatography and Detection of 2-isopropyl-4-methyl-6-hydroxy-
pyrimidinyl Diethy1 Phosphate and 2-isopropyl-4-methyl-6-
hydroxypyrimidinyl Diethyl thionophosphate", P. V. Jacques, et al.,
Bull. soc. chim. France 1955. 1282; Chem. Abs. 50, 1530d (1956).
(5) "Determination of Residues of 0,0-diethyl 0-(2-isopropyl-6-methyl-
4-pyrimidyl) Phosphorothioate in Milk", R. C. Blinn, et al., J. Agr.
Food Chem. 3, 1013-16 (1955); Chem. Abs. 50, 44181 (1956).
(6) "Methods of Analysis for Some New Agents Which are for Pest Control",
R. Sutter, et al., Z. Anal. Chem. 147. 173-84 (1955); Chem. Abs. 49,
16301b (1955).
1956
(7) "Insecticidal Phosphate Esters", J. R. Geigy A.-G. U.S. 2.754.243-4
and U.S. 2.754.302. July 10, 1956; Chem. Abs. 50, 12122g (1956).
1957
(8) "Biochemical Studies on the Degradation Products of Diazinon",
K. B. Augustinsson, et al., Experientia .13, 438-9 (1957); Chem.
Abs. 52, 4748h (1958).
(9) "Diazinon, Its Decomposition Products, and Its Properties",
A. Margot, et al., Helv. Chim. Acta 40, 1562-73 (1957); Chem.
Abs. 52, 7326e (1958).
75
-------
1958
(10) "Quantitative Control Method for Detection of Insecticidal
Residues on Fruits and Vegetables", W. Weimann, Z. Lebensm.-
Unter-such. u. -Forsch. 107. 504-10 (1958); Chem. Abs. 52,
16644g (1958).
(11) "Dialkyl Thiophosphates and N, N-dialkylcarbamates of Hetero-
cyclic Compounds", N. N. Mel'nikov, et al., Org. Insektofungitsidy
i Gerbitsidy 1958. 108-17; Chem. Abs. 55, 3600a (1961).
1959
(12) "Detection of Thiophosphoric Esters", R. Fischer, et al., Sci.
Phann. 27, 1-6 (1959); Chem. Abs. 53, 16830a (1959).
(13) "The Extraction and Identification of Parathion and Diazinon
From Lettuce", R.E.J. Moddes, et al., J. Assoc. Offic. Agr.
Chemists 42, 208-11 (1959); Chem. Abs. 53, 9511a (1959).
(14) "Note on the Conversion of Some Organophosphate Pesticides to
Less Polar Compounds by Ultraviolet Light", J. W. Cook, et al.,
J. Assoc. Offic. Agr. Chemists 41, 211-12 (1959); Chem. Abs.
53, 9556b (1959).
(15) "Dispersible Pesticide Pastes", J. R. Geigy, Akt.-Ges. Brit.
882,869, Nov. 4, 1959; Chem. Abs. 54, 499c (1960).
(16) "Residues of Plant Protective Agents on or in Crop Materials
VI. Biological Detection of Diazinon and Parathion Residues in
Radishes and Carrots", E. Mosebach, et al., Nachrbl. Deut.
Pflanzenschutzdienst (Braunschweig) _11 150-55 (1959) ; Chem.
Abs. .58, 7601d (1964).
1960
(17) "Residues of Plant Protective Agents on or in Crop Materials.
VI. Biological Detection of Diazinon and Parathion Residues in
Radishes and Carrots", E. Mosebach, et al., Nachrbl. Deut.
Pflanzenschutzdienst (Bruanschweig) .12, 129-33 (1960); Chem.
Abs. 58, 760Id (1964).
(18) "A New Bio-Assay Method for Insecticide Residues", T. Suzuki,
et al., Japan, J. Exptl. Med. .30, 75-81 (1960); Chem. Abs. 54,
17775i (1960).
(19) "Determination of Diazinon Residues in Olive Oil", M. Doretti,
Rend. ist. super, sanita 23, 294-300 (1960); Chem. Abs. 54,
23107g (1960).
76
-------
(20) "Colorimetric Method for the Determination of Diazinon", A.
Irudayasamy, et al., Current Sci. (India) 29. 471-2 (1960);
(1960); Chem. Abs. 55, 12752e (1961).
(21) "The Determination of Residual Diazinon on Olive Fruits",
A. Guvener, Bitki Koruma Bulteni J., No. 3, 17-24 (1960); Chem.
Abs.,56, 15872e (1962).
(22) "The Influence of Human Plasma Cholinesterase Activity and In-
hibitor Conversion in Vitro on the Enzymic Determination of
Organophosphorus Insecticides", K. Kojima, et al., Bochu-Kagaku
J25(l), 30-41 (1960); Chem. Abs. 61, 24l5g (1967).
(23) "Automated Enzymic Assay of Organic Phosphate Pesticide Residues",
G. D. Winter, Ann. N.Y. Acad. Sci. 87, 875-82 (1960); Chem. Abs.
55, 17997g (1961).
1961
(24) "The Effect of Ultraviolet Light (2537 A.) on 141 Pesticide
Chemicals by Paper Chromatography", L. C. Mitchell, J. Assoc.
Offic. Agr. Chemists 44, 643-712 (1961); Chem. Abs. 56,
3849e (1962).
(25) "Toxicological Detection and Determination of Thiophosphoric
Acid Esters. II., R. Fischer, et al., Pflanzenschutz Her. 27.
165-76 (1961); Chem. Abs. 56, 5677e (1962).
(26) "Thin-Layer Chromatographic Detection of Insecticides", J. Baeumler,
et al., Helv. Chim. Acta 44, 1162-4 (1961); Chem. Abs. 56, 12036a
(1962).
(27) "A Method for the Detection of Diazinon in Viscera", 6. Rao,
et al., J. Indian Med. Assoc. 37, 603-4 (1961); Chem. Abs. 60,
1640,7d (1964).
(28) "The Test for Quantitative Determination of Esters of Thio-
phosphoric Acid in Biological Material", R. Fischer, et al.,
Arch. Toxlkol. JL9, 119-40 (1961); Chem. Abs. 58, 17130c (1962).
1962
(29) "Esterace Inhibition Technique for the Detection of Organo-
phosphorus Pesticides", W. P. McKinley, et al., J. Assoc. Offic.
Agr. Chemists 45, 467-731 (1962); Chem. Abs. 57, 382Ib (1962).
77
-------
(30) "The Insecticide Residues from the Control of Rhagoletis Cerasi
with the Organophosphorus Insecticide Lebaycid", H. Maier-Bode
Anz. Schaedlingskunde 35, 49-53 (1962); Chem. Abs. 57, 7671e
(1962). ~~~
1963
(31) "Chromatographic Identification of Some Organophosphate
Insecticides in the Presence of Plant Extracts", H. F. MacRae,
et al., J. Agr. Food Chem. .11, 174-8 (1963); Chem. Abs. 58,
11907d (1963).
(32) "Thin-Layer Chromatography for Insecticide Analysis", C. Walker,
et al., J. Assoc. Offie. Agr. Chemists 46. 250-61 (1963); Chem.
Abs. 58, 14626g (1963).
(33) "Persistence of Mosquito Larvicides in Water", M. S. Mulla,
Mosquito NewsJ23(3), 234-7 (1963); Chem. Abs. 60, 2271c (1964).
(34) "Development of Double Isotope Derivative Dilution Analyses
for Selected Food Additives", R. L. Bogner, et al., U.S. At.
Energy Comm. NSEC-85. 99 pp. (1963); Chem. Abs. £1, 2387f (1964)
(35) "Phosphoric Acid Esters", H. Kataoka, Geigy Chemical Corp.
U.S. 3.107.245. Oct. 15, 1963; Chem. Abs. 60, 2966f (1964).
(36) "Phosphoric Acid Esters", Geigy Chemical Corp. U.S. 3.107.246.
Oct; 15, 1963; Chem. Abs. 60, 2966h (1964).
(37) "Applications of the Microcoulometric Titrating System as a
Detector in Gas Chromatography of Pesticide Residues", J. A.
Challacombe", Residue Rev. .5, 57-72 (1963)(Pub. 1964); Chem.
Abs. 61, 9975h (1964).
1964
(38) "Diazinon", A. Margot, et al., Anal. Methods Pesticides, Plant
Growth Regulators Food Additives (Gunter Zweig, editor.
Academic) 2, 109-24 (1964); Chem. Abs. 61, 11263f (1964).
(39) "Evaluation of Minute Amounts of Some Phospho-Organic Com-
pounds in Plant Material by Means of Paper Chromatography",
J. Zadrozinska, Roczniki Panstwowego Zakladu Hig. 15(1).
5-12 (1964); Chem. Abs. .61, 6262a (1964).
(40) "Detection and Identification of the Residues of the Organo-
phosphorus Pesticides by Gel Electrophoresis", P. Bruaux,
et al., Ann. Biol. Clin. (Paris) 22(3-4), 375-98 (1964); Chem.
Abs. 61, 6303a (1964).
78
-------
(41) "The determination of Traces of Phosphoric Esters by Oscillo-
graph! c Polarography", P. Nangniot, Anal. Chim. Acta 31(2).
166-74 (1964); Chem. Abs. .61, 12563c (1964).
(42) "The Detection of Organophosphorus Pesticides on Thin-Layer
Chromatograms", P. J. Bunyan, Analyst 89(1062), 615-18 (1964);
Chem. Abs. 61, 15282f (1964).
(43) "Thin-Layer Chromatography for Organothiophosphate Pesticide
Residue Determination", M. F. Koracs, Jr., J. Assoc. Offic. Agr.
Chemists 47(6), 1097-102 (1964); Chem. Abs. 62, 4517h (1965).
(44) "Determination of Some Organophosphorus Insecticides by Gas-
Liquid Partition Chromatography", M. Horiguchi, et al., Chem.
Pharm. Bull. (Tokyo) .12(11), 1315-19 (1964); Chem. Abs. .62,
5823g (1965).
(45) "Identification and Analyses of Five Organophosphate Pesticides:
Recoveries from Crops Fortified at Different Levels", R. W.
Storherr, et al., J. Assoc. Offic. Agr. Chemists 47(6), 1087-93
(1964); Chem. Abs. 62, 5824e (1965).
(46) "Detection and Separation of the Most Important Organophosphorus
Pesticides by Thin-Layer Chromatography", M. Salame, J. Chromatog,
.16(3), 476-80 (1964); Chem. Abs. 62, 11090b (1965).
(47) "Unidimensional, Multiple-Unidimensional, and Bidimensional
Thin-Layer Chromatographic Separation of Organophosphorus In-
secticides and Their Residues in Vegetable Oils", P. Melchiorri,
et al., Farmaco, (Pavia), Ed. Prat. 12(12), 610-27 (1964); Chem.
Abs. 62, 12369b (1965).
(48) "Enzymic Control of the Presence of Phosphoric Acid Esters in
Italian Olive Oils", L. Lipparini, Atti Conv. Qualita, 3°,
Perugia, Italy 1964, 105-9; Chem. Abs. 63, 3177h (1965).
1965
(49) "Selective Detection of Phosphorus, Sulfur, and Halogen Com-
pounds in the Gas Chromatography of Drugs and Pesticides",
H. P. Burchfield, et al., J. Gas Chromatog. 3(1), 28-34 (1965);
Chem. Abs. 62, 11629e (1965).
(50) "Gas-Liquid Chromatography of Organophosphorus Pesticides",
I. Kanazawa, et al., Agr. Biol. Chem. (Tokyo) .29(1), 56-60
(1965); Chem. Abs. 62, 12385a (1965).
79
-------
(51) "The Detection of Thiophosphate Insecticides on Paper Chromato-
grams with Congo Red", A. Irudayasamy, et al., Analyst 90(1073).
503-4 (1965); Chem. Abs. 63, 15470g (1965).
(52) "Screening Procedure for Organothiophosphate Pesticide Residues
on Fruits and Vegetables Using Microcoulometric Gas Chromato-
graphy. R. C. Nelson, J. Assoc. Offie. Agr. Chemists 48(4),
752-9 (1965); Chem. Abs. 63, 18932d (1965).
(53) "Determination of Organophosphorus Insecticide Residues Using the
Emission Spectrometric Detector", C. A. Bache, et al., Anal.
Chem. .37(12), 1477-80 (1965); Chem. Abs. 64, 1288a (1966).
(54) "Determination of Selected Phosphoorganic Pesticides (Parathion,
Methylparathion, Diazinon, Malathion, Gusathion, Meta-Systox, and
Dipterex) by Thin-Layer Chromatography Method", J. Zadrozinska,
Roczniki Panstwowego Zakladu Hig. .16(4), 397-405 (1965); Chem.
Abs. 64, 2684h (1966).
(55) "Simultaneous and Selective Detection of Phosphous, Sulfur, and
Halogen in Pesticides by Microcoulometric Gas Chromatography",
H. P. Burchfield, et al., J. Agr. Food Chem. .13(6), 511-16 (1965);
Chem. Abs. 64, 4l93b (1966).
(56) "Phosphorimetric Study of Some Common Pesticides", H. A. Moye,
et al., J. Agr. Food Chem. .13(6), 516-18 (1965); Chem. Abs. 64,
4l93c (1966).
(57) "A Sweep Codistillation Cleanup Method for Organophosphate
Pesticides. I. Recoveries From Fortified Crops", R. W. Storherr,
et al., J. Assoc. Offie. Agr. Chemists 48(6), 1154-8 (1965); Chem.
Abs. 64, 8847d (1966).
(58) "Phytotoxicity to Tobacco of Fertilizer-Organophosphate Com-
binations Against the Cyclodiene-Resistant Root Maggot, Hylemya
Liturata", J. A. Begg, Tobacco Sci. 9, 179-80 (1965); Chem.
Abs. 64, 8870a (1966).
(59) "Identification and Quantitative Determination of Phosphorus In-
secticides in Biological Material. II.", R. Fischer, et al.,
Arch. Toxikol. .21(2), 101-20 (1965); Chem. Abs. 64, 16554b (1966).
(60) "Determination of Diazinon in Water-Dispersible Powder Concen-
trates by Gas-Liquid Chromatography", J. Kanazawa, Bunseki
Kagaku.l4(l), 20-3 (1965); Chem. Abs. 62, 11632f (1965).
(61) "Separation of Mixtures and Detection of Trace Amounts of Some
Organophosphorus Pesticides in Plant Material by Means of Paper
Chromatography", J. Zadrozinska, Roczniki Panstwowego Zakladu
Hig. .16(1), 53-63 (1965); Chem. Abs. 62, 16876g (1965).
80
-------
(62) "Use of Thin-Layer and Semipreparative Gas-Liquid Chromatography
in the Detection, Determination, and Identification of Organo-
Phosphorus Pesticide Residues", D. C. Abbot, et al., Proc. SAC
(Soc. Anal. Chem.) Conf., Nottingham, Engl. 1965. 121-33, dis-
cussion 133-4; Chem. Abs. 65, 19210f (1966).
1966
(63) "Detection and Estimation of Diazoxon-^C in Vivo by Counter-
Current Distribution and Inhibition Assay", C. A. Schunter,
et al., Biochim. Biophys. ActaJJLS(l), 225-7 (1966); Chem. Abs.
64, 13324f (1966).
(64) "Dual-Band Preparative Thin-Layer Chromatography for the Separa-
tion of Diazinon and Related Compounds From Plant Material",
D. R. Gilmore, et al., J. Chroma tog. .21(1), 148-9 (1966); Chem.
Abs. 64, 18299e (1966).
(65) "An Improved Screening Method for Chlorinated and Thiophosphate
Organic Insecticides in Foods and Feeds", B. L. Samuel, J. Assoc.
Offic. Anal. Chemists 49(2), 346-53 (1966); Chem. Abs. £5, 2894b
(1966).
(66) "Residue Analysis of Agricultural Chemicals. III. Electron-
capture Gas Chromatography of Various Pesticides", J. Kanazawa,
et al., Nippon Nogei Kagaku Kaishi 40(4), 178-84 (1966); Chem.
Abs. 457If (1966).
(67) "Determination of Organophosphorus Insecticide Residues Using
Cooke's Emission Spectroscopic Detector", C. A. Bache, et al.,
Residue Rev. 12, 35-44 (1966); Chem. Abs. 65, 7895e (1966).
(68) "Screening Procedure for Organothiophosphate Pesticide Residues
on Fruits and Vegetables by Microcoulometric Gas Chromatography",
R.,C. Nelson, J. Assoc. Offic. Anal. Chemists 49(4), 763-6
(1966); Chem. Abs. 65, 17598a (1966).
(69) "Sodium Flame Detector of Increased Stability for Phosphorus-
Containing Pesticides", D. R. Coahran, Bull. Environ. Contarn.
Toxicol. 1(4), 141-8 (1966); Chem. Abs. 65, 17623d (1966).
(70) "Semiquantitative Determination of Organophosphorus Insecticides
by the Ring-Oven Technique With Preliminary Thin-Layer Chromato-
graphy. I.", M. B. Celap, et al., Analyst .91(1086), 595-7
(1966); Chem. Abs. 65, 20772h (1966).
(71) "Low Pressure Emission Spectrometric Determination of Parts Per
Billion Residue Levels of Phosphorus Insecticides",C. Bache, et al.,
Anal. Chem". 38(12)| 1757-8 (1966); Chem. Abs. 66~1817J (1967).
81
-------
(72) "Gas Chromatographic Analysis of Pesticides. II. Gas Chromato-
graphic Determination of Organophosphorus Pesticides", H. Takehara,
et al., Nippon Nogei Kagaku Kaishi 40(11), 394-400 (1966)(Japan);
cf. Sankyo Kenkyujo Nenpo .17, 180 (1965); Chem. Abs. .66, 94l59w
(1967).
(73) "Electrochemical Methods for Quantitative Analysis of Pesticide
Residues", P. Nangniot, Meded. Rijksfac. Landbouwwetensch., Gent
1966. 31(3), 447-73; Chem. Abs. 69, 66438e (1968).
. :f
(74) "Methods for Market Control of Organophosphate Residues in Fruit
and Vegetables", Chr. Krause, Z. Pflanzenkr. Pflanzenschultz.
1966. 21(6), 335-45; Chem. Abs. JO, 18968b (1969).
1967
(75) "Detector Cell for Measuring Picogram Quantities of Organo-
phosphorus Insecticides, Pyrethrin Synergists, and Other Compounds
by Gas Chromatography", W. N. Bruce, J. Agr. Food Chem. 15(1).
178-81 (1967); Chem. Abs. 66, 54499a (1967).
(76) "0,0-Dialkyl 0-Aryl Thiophosphates", Geigy Chemical Corp.,
U.S. 3.329.678. July 4, 1967; Chem. Abs. .67, 108664s (1967).
(77) "Collaborative Study of a Method for Multiple Organophosphorus
Pesticide Residues in Konfatty Foods", J. R. Wessel, J. Assoc.
Offie. Anal. Chem. £0(2), 430-9 (1967); Chem. Abs. 66, 114635d
(1967).
(78) "Improved Gas Chromatographic Systems for Determining Organo-
chlorine Pesticide Residues in Wildlife", J. H. Simmons, et al.,
J. Chromatogr. .27(1), 253-5 (1967); Chem. Abs. £7, 10437v
(1967).
(79) "Rapid Method for Surface Residues of Organophosphorus Pesticides
by Total Phosphorus", E. J. Broderick, et al., J. Agr. Food Chem.
JJ5(3), 454-6 (1967); Chem. Abs. ,67, 20674j (1967).
'*•
(80) "A Thin-Layer Chromatographic Screening Test for Organophosphorus
Pesticide Residues", D. C. Abbot, et al., Analyst (London) 92
(1092), 170-5 (1967); Chem. Abs. 67, 31604n (1967).
(81) "Systematic Applications of Gas-Liquid Chromatography in Toxi-
cology. V. Pesticides and Evaluation of Toxic Levels", N. C.
Jain, et al., Microchem. J. 12(2), 265-72 (1967); Chem. Abs.
67, 42144p (1967).
82
-------
(82) "Sweep Codistillation Cleanup of Milk for Determination of Organo-
phosphate and Chlorinated Hydrocarbon Pesticides", R. R. Watts,
et al., J. Assoc. Offic. Anal. Chem. 50(3), 581-5 (1967); Chem.
Abs. £7, 42609u (1967).
(83) "Sweep Codistillation Cleanup of Fortified Edible Oils for
Determination of Organophosphate and Chlorinated Hydrocarbon
Pesticides", R. W. Storherr, et al., J. Assoc. Offic. Anal.
Chem. 50(3);, 605-15 (1967); Chem. Abs. .67, 42612q (1967).
(84) "Procedure for Nine Organothiophosphate Pesticide Residues on
Fruits and Vegetables, Using Microcoulometric Gas Chromatography",
R. C. Nelson, J. Assoc. Offic. Anal. Chem. 50(4), 922-6 (1967);
Chem.'Abs. .67, 72514b (1967).
(85) "Thin-Layer Chromatographic Separation Scheme for Insecticidally
Active Phosphoric Acid Esters", J. A. Guth, Pflanzenschutzberichte
35(9-10), 129-43 (1967); Chem. Abs. 67, 72784q (1967).
(86) "Gas-Liquid Chromatographic Separation of Some Organophosphate
Pesticides, Their Hydrolysis Products, and Oxons", I. H. Suffet,
et al., Environ. Sci. Technol. 1(8), 639-43 (1967); Chem. Abs.
.67, 107614p (1967).
(87) "The Gas-Chromatographic Determination of Organophosphorus
Pesticides. II. A Comparative Study of Hydrolysis Rates",
J. H. Ruzicka, et al,, J. Chromatogr. .31(1), 37-47 (1967);
Chem. Abs. 68, 2191r (1968).
(88) "Mechanisms of Monofluoroacetanilide Poisoning in Mammals.
VIII. Organophosphorus Compounds as Specific Inhibitors of
Fluoroacetanilide Amidohydrolase", T. Nakamura, et al., Agr.
Biol. Chem. .31(11), 1288-93 (1967); Chem. Abs. 68, 2115lu
(1968).
(89) "The Gas-Chromatographic Examination of Organophosphorus Pesti-
cides and Their Oxidation Products", J. Ruzicka, et al., J.
Chromatogr. .30(1), 92-9 (1967); Chem. Abs. 68, 21155y (1968).
(90) "Temperature-Programmed Gas Chromatography of 20 Phosphorus-
Containing Insecticides on 4 Different Columns and Its Applica-
tion to the Analysis of Milk and Corn Silage", M. C. Bowman,
et al., J. Assoc. Offic. Anal. Chem. 50(6), 1228-36 (1967);
Chem. Abs. j68, 3822Iq (1968).
(91) "The Susceptibility of Culex Pipiens Molestus in Israel to
Several Insecticides in 1958-1960 and 1965", A. Barkai, et al.,
Mosquito News .27(2), 191-8 (1967); Chem. Abs. 68, 94863n (1968).
83
-------
(92) "Enzymic Assays of Thionophosphate Insecticides and of Iheir
Activated Products", D. Palut, et al., Rocz. Panstw. Zakl.
Hig. 1967. 18(5), 527-33; Chem. Abs. 69, 18255w (1968).
(93) "Modified Hydrogen Flame-lonization Detector, Highly Sensitive
and Selective for Phosphates", R. V. Hoffman, Lect. Gas.
Chromatogr. 1966 1967, 137-47; Chem. Abs. 70, 95709v (1969).
1968
(94) "Detection of Diazinon Residues in Some Foods Treated by
Labeled Diazinon", P. DiMattei, et al., Farmaco, Ed. Prat.
1968. 23(5), 238-40; Chem. Abs. 69, 1840k (1968).
(95) "Collaborative Study of the Ethyl Acetate Extraction, Sweep
Co-distillation Cleanup, and GLC Determination, Using Six
Parent Organophosphate Pesticides", R.'W. Storherr, et al.,
J. ASS.OC. Offic. Anal. Chem. 1968. 51(3), 662-5; Chem. Abs.
69, 9899g (1968).
(96) "Collaborative Study of Three Gas Chromatographic Dual Detec-
tion Systems for Analysis of Multiple Chlorinated and Organo-
phosphorus Pesticides", J. R. Wessel, J. Assoc. Offic. Anal.
Chem. 1968. 51(3), 666-75; Chem. Abs. 69, 9900a (1968).
(97) "Consistency of R8t Values of Six Organophosphorus Pesticides
Resolved by Thin-Layer Chromatography in the Presence of Plant
Extracts Without Elaborate Clean-Up", C. E. Mendoza, et al.,
Analyst (London) 1968. 93(1111), 688-90; Chem. Abs. 70, 10566y
(1969).
(98) "Procedure for Semiquantitative Confirmation of Some Organo-
phosphorus Pesticide Residues in Plant Extracts", P. J. Wales,
et al., Analyst (London) 1968. 93(1111), 691-3; Chem. Abs. 22,
10567z (1969).
(99) "Detection of Thio- and Dithiophosphoric Esters and Esterase
Inhibitor on Thin-Layer Chromatograms", H. Beitz, et al., Z.
Chem. .1968; 8(10), 387-8; Chem. Abs. TQt 10612k (1969).
(100) "Phosphoric Esters of Substituted Hydroxypyrimidines and Phenols",
Geigy Chemical Corp. U.S. 3.367.935. Feb. 6, 1968; Chem. Abs. .69,
27454n (1968).
(101) "Microanalysis of Some Organophosphorus Pesticides by a
Spectrophotometric Method Using Safranine Reagent", K. Suzuki,
et al., Bunseki Kaeaku 1968. 17(10), 1279-83; Chem. Abs. JJO,
27904e (1969).
84
-------
(102) "Extraction of Organochlorine and Organophosphate Insecticides
From Lake Waters", H. B. Pionke, et al., Analyst (London)
1968. 93(1107), 363-7; Chem. Abs. 69, 38663f (1968).
(103) "Determination of Organophosphorus Insecticides in Plant
Material", I. Pejkovic-Tadic, et al., Hrana Ishrana 1968. 9(1),
29-31; Chem. Abs. .69, 58436n (1968).
(104) Enzymic Detection of Ten Organophosphorus Pesticides and
Carbaryl on Thin-Layer Chromatograras: An Evaluation of Indoxyl,
Substituted Indoxyl, and 1-Naphthyl Acetates as Substrates of
Esterases", C. E. Mendoza, et al., Analyst (London) 93(1102),
34-8 (1968); Chem. Abs. 68, 58668u (1968).
(105) "Nuclear Magnetic Resonance Studies of Phosphorus(V) Pesticides.
I. Chemical Shifts of Protons as a Means of Identification of
Pesticides", H. Babad, et al., Anal. Chim. Acta 41(2), 259-68
(1968); Chem. Abs. 618, 77181w (1968).
(106) "Sodium Methylate Treatment of Cleaned Up Plant Extracts in
Confirmation of Some Pesticide Residues by Gas-Liquid and Thin-
Layer Chromatography", C. E. Mendoza, et al., J. Assoc. Offie.
Anal. Chem. 1968. 51(5), 1095-101; Chem. Abs. 69, 75626s (1968).
(107) "High-Resolution N.M.R. Spectra of Pesticides. I. Organo-
phosphorus Pesticides", L. H. Keith, et al., J. Assoc. Offie.
Anal. Chem. 1968. 51(5), 1063-94; Chem. Abs. £9, 75848r (1968).
(108) "Thin-Layer Chromatography of Organophosphorus Insecticides With
Several Adsorbents and Ternary Solvent Systems", M. E. Getz,
et al., J. Assoc. Offic. Anal. Chem. 1968. 51(5), 1101-7; Chem.
Abs. 69, 75850k (1968).
(109) "Cleanup Procedure for Water, Soil, Animal, and Plant Extracts
for the Use of Electron-Capture Detector in the Gas Chromato-
graphic Analysis of Organophosphorus Insecticide Residues",
A. M. Kadoum, Bull. Environ. Contain. Toxicol. 1968. 3(4),
247-53; Chem. Abs. 69, 75644w (1968).
(110) "Polyamide Layer Chromatography of Organophosphorus Pesticides",
J. T. Huang, et al., J. Pharm. Sci. 1968. 57(9), 1620-1; Chem.
Abs. £9, 85652m (1968).
(Ill) "Automated Differential Screening Method for Organophosphorus
Pesticides", D. C. Leegwater, et al., J. Sci. Food Agr. 1968.
19(9), 513-18; Chem. Abs. 69, 95147q (1968).
85
-------
(112) "Detection of Cholinesterase-Inhibiting Pesticides Following
Separation on Thin-Layer Chromatograms", W. Winterlin, et al.,
J. Agr. Food Chem. 1968. 16(5), 808-12; Chem. Abs. 69, 95350a
(1968). ~~
(113) "Flame lonization Detector for Organophosphorus Compounds",
United States Dept. of Health, Education and Welfare and United
States Dept. of Agriculture). U.S. 3.372.994. March 12, 1968;
Chem. Abs. 68, 104l49a (1968).
(114) "The Use of Gas Chromatography with Electron Capture in the
Analysis of Organophosphate Pesticides", M. Salame, Ann. Biol.
Clin. (Paris) 1968. 26(7-9), 1011-21; Chem. Abs. £9, 105280u
(1968).
(115) "Detection of Pesticides by Reversed Phase Paper Chromatography",
R. T. Wang, et al., Chung Kuo Nung Yen Hua Hsueh Hui Chih 1968.
6(3-4); Chem. Abs. .71, 111799c (1969).
(116) "Determination of Ectoparasiticides in Cattle Baths", G. Szekely,
et al., Int. Symp. Chromatogr. Electrophoresis, 5th 1968 (Pub.
1969), 464-6; Chem. Abs. 72, 20804e (1970).
(117) "Qualitative Analysis of Synthetic Organic Pesticides by Spot
Tests", M. Kanda, et al., Nippon Hoigaku Zasshi 1968. 22(3),
229-51; Chem. Abs. 72, 65726x (1970).
(118) "Microwave-Powered Emission Determination of Residues of
Organic Bromine, Chlorine, Iodine, Phosphorus, and Sulfur
Pesticides in a Helium Plasma", C. A. Bache, et al., Biomed.
Appl. Gas Chromatogr. 1968. 2, 165-78; Chem. Abs. 73, 76019r
(1970).
1969
(119) "Pesticide Residues. Indoxyl Acetate Spray Reagent for Fluro-
genic Detection of Cholinesterase Inhibitors in Environmental
Samples", R. L. Schutzmann, J. Assoc. Offie. Anal. Chem. 1969.
52(1), 151-6; Chem. Abs. JO, 56345d (1969).
(120) "Pesticide Residues. Recovery of 65 Organophosphorus Pesti-
cides From Florisil With a New Solvent-Elution System",
H. Beckman, et al., J. Assoc. Offie. Anal. Chem. 1969. 52(2),
286-93; Chem. Abs. 70, 86520z (1969).
(121) "Determination of Diazinon and its Oxygen Analog in Animal
Tissues by Gas Chromatography", A. F. Machin, et al., Analyst
(London) 1969. 94(1116), 221-5; Chem. Abs. .71, 2175a (1969).
86
-------
(122) "Gas Chromatography of Organophosphorus Pesticides: Retention
Times and Response Data on Three Columns1.1, R. R. Watts, et al.,
J. Assoc. Offic. Anal. Chem. 1969. 52(3), 513-21; Chem. Abs. 71,
12019s (1969).
(123) "Alkaline Precolumn for Use in Gas-Chromatographic Pesticide
Residue Analysis", G. A. Miller, et al., J. Assoc. Offic. Anal.
Chem. 1969. 52(3), 548-53; Chem. Abs. TL* 12021m (1969).
(124) "Charcoal Column Cleanup Method for Many Organophosphorus
Pesticide Residues in Crop Extracts", R. R. Watts, et al.,
J. Assoc. Offic. Anal. Chem. 1969. 52(3), 522-6; Chem. Abs. ,71,
21124z (1969).
(125) "Extraction of Organochlorine and Organophosphate Insecticides
From Lake Waters", J. G. Konrad, et al., Analyst (London)
1969. 94(1119), 490-2; Chem. Abs. .71, 533l6e (1969).
(126) "Simple and Rapid Separation of Pesticides by Polyamide
Chromatography", R. T. Wang, et al., J. Chromatogr. 1969.
42(3), 416-18; Chem. Abs. TL» 59980p (1969).
(127) "Collaborative Study of Confirmative Procedures by Single-
Sweep Oscillographic Polarography for the Determination of
Organophosphorus Pesticide Residues in Nonfatty Foods",
R. J. Gajan, J. Assoc. Offic. Anal. Chem. 1969. 52(4), 811-17;
Chem. Abs. .71, 79813 q (1969).
(128) "Determination of Organophosphorus Pesticides in Water",
G. Zweig, et al., Residue Rev. 1969. 26. 17-36; Chem. Abs.
71, 80107u (1969).
(129) "Fate of Diazinon in Field-Sprayed Agricultural Crops, Soil,
and Olive Oil", D. 0. Eberle, et al., J. Assoc. Offic. Anal.
Chem. 1969. 52(5), 1067-74; Chem. Abs. TL» 100484v (1969).
(130) "Carboxylesterase Inhibition Assay to Estimate Parathion,
Malathion, and Diazinon in Lettuce Extracts", D. C. Villeneuve,
et al., Bull. Environ. Contarn. Toxicol. 1969. 4(4), 232-9;
Chem. Abs. .71, 111488a (1969).
(131) "Rapid Spectrophotometric Determination of Zinc in Treated
Woods", G. Deon, Cent. Tech. Forest. Trop., Nogent-sur-Marne,
Fr., Note Tech. 1969. No. 10, 27 pp; Chem. Abs. 72> 13l380h
(1970).
(132) "Separation and Identification of Parathion and Its Metabolites
in Autopsy Tissues by Thin-Layer Chromatography", S. N. Tewari,
et al., Mikrochim. Acta 1970. (1), 58-60; Chem. Abs. 72.
131387r (1970).
87
-------
(133) "Pesticide Residues. XIX. Determining Pesticide Residues in
Natural Waters. I. General Analytical Methods", R. Mestres,
et al., Ann. Fals. Expert, Chim. 1969. 62(685), 75-85; Cheni.
Abs. 73, 3409Ic (1970).
(134) "Analysis of Chlorinated and Organic Phosphorus Pesticides by
Gas Chromatography", M. Kanda, et al., Nippon Hoigaku Zasshi
1969. 23(6), 477-86; Chem. Abs. 73, 653lOc (1970).
(135) "Simple and Rapid Reversed Phase Thin-Layer Chromatography
of Pesticides", R. T. Wang, et al., Hua Hsueh 1969. (4), 80-5,
Chem. Abs. j^> 2953q (1971).
(136) "Chromatographic Determination of Trace Amounts of Pesticide
Residues", M. Beroza, et al., Trace Subst. Environ. Health-3,
Proc. Univ. Mo. Annu. Conf., 3rd 1969 (Pub. 1970), 331-51;
Chem. Abs. 74, 2963t (1971).
(137) "Residue of Diazinon in Cabbage After Treatment Against
Cabbage Root Fly (Hylemyia Brassicae)", Z. Zwolinska-Sniatalowa,
et al., Biul. Warzywntczy 1969. 10, 147-52; Chem. Abs. J4
75289n (1971).
1970
(138) "Screening Procedures for Organophosphorus, Organochlorine, and
£arbamate Pesticide Residues on Tobacco", E. Nesemann, et al.,
Beitr. Tabakforsch 1970. 5(5), 207-14; Chem. Abs. 73, 4531v
(1970).
1969
(139) "Determination of Insecticides Based on Phosphoric Acid Esters
b^y Means of the Chemiluminescence of Luminol", K. Weber,
et al., Acta Pharm. Jugoslav. 1969. 19(2), 47-53; Chem. Abs.
72, 77835v (1970).
(139a) "Channel Layer 6hromatography, With a Rapid Spotting Technique, for
One-Stage Cleanup in Pesticide Residue Analysis", Hetherington, R..M.,
et al., J. Ass. Offie. Anal. Chem. 1970. 53(1), 146-8, Chem. Abs.
22, 77840t (1970).
1970
(140) "Rapid Procedures for the Routine Determination of Organo-
phosphorus Insecticide Residues in Vegetables. I. Determina-
tion of Hexane-Soluble Insecticides by Gas-Liquid Chromatography
and Total-Phosphorus Procedures", D. J. Sissons, Chromatogr.
1970. 47(3), 328-40; Chem. Abs. 73, 23946J (1970).
88
-------
(141) "GLC [Gas-Liquid Chromatographic] Retention Times of Pesticides
and Metabolites Containing Phosphorus and Sulfur on Four Thermally
Stable Columns", M. C. Bowman, et al. , J. Assoc. Offic. Anal.
Chem. 1970. 53(3), 499-508; Chem. Abs. 73, 24l79y (1970).
(142) "Thin-Layer Chromatographic Separation and Chomogenic Detection
of Diazinon and Some of its Known or Suspected Metabolites and/or
Degradation Products", M. Siewierski, et al., J. Assoc. Offic.
Anal. Chem. 1970. 53(3), 514-18; Chem. Abs. 73, 24181t (1970).
\
(143) "Initial Effectiveness and Residual Toxicity of Several Insecti-
cides Against the Southern Potato Wirewonn", A. Day, J. Econ.
Entomol. 1970. 63(2), 511-13; Chem. Abs. 73, 24257x (1970).
(144) "Detection, Separation, and Quantitative Recovery of Thirteen
Organophosphorus Pesticides on Silica Gel GF254 Thin-Layer
Chromatograms" , D. C. Villeneuve, et al., J. Chromatogr. 1970.
48(3), 567-71; Chem. Abs. 73, 54922c (1970).
(145) "Proton Magnetic Resonance Studies on Organophosphorus Pesti-
cides. I. Doubling of Resonances Induced by Asymmetry",
'Z. Gaibel, et al., Va. J. Sci. 1970. 21(1), 14-16; Chem. Abs.
23, 71883h (1970).
(146) "Modified Enzymic Detection Method for Thin- Layer Chromatograms
of Pesticides", G. F. Ernst, et al., J. Chromatogr. 1970. 49(2),
325-8; Chem. Abs. 73, 76024p (1970).
(147) "Simultaneous Detection of Some Organophosphorous Pesticides in
Whole Wheat Flour", C. E. Mendoza, et al., Bull. Environ.
Contam. Toxicol. 1970. 5(3), 276-8; Chem. Abs. 73, 97420e (1970).
(148) "Insecticidal Mffects on the Jhot migration of Aedes Aegvpti
Larvae and the Possibilities for the use of the T-50 Bifassay
for Determination of Insecticide Residues", Elezovic I et al
al
?ir~J0«™Phy ^termination of Diazinon Residues in Plants"
it: '• -'• ^ 2(6) '
(150) "Correlations Between Phosphorus-31 NMR Chemical Shifts and
Structures of Some Organophosphorus Pesticides", R. T. Ross,
et al., Anal. Chlm. Acta. 1970. 52(1), 139-41; Chem. Abs. 74,
31000g (1971).
1971
(151) "Evaluation of Two Extraction Procedures for Pesticide Residues
Resulting From Foliar Application and Root Absorption", J. A.
Burke, et al., J. Assoc. Offic. Anal. Chem. 1971. 54(1), 142-6;
Chem. Abs. 2£. 75518m (1971).
89
-------
(152) "Insecticide Studies at the Mosquito Research and Control Unit,
Grand Cayman, British West Indies", J. A. Armstrong, Mosquito
News 1971. 31(1), 1-11; Chem. Abs. 74, 140002e (1971).
(153) "Biodegradability Test for Insecticides", H. Ha Ivor son, et al.,
Can. J. Microbiol. 1971, 17(5), 585-91; Chem. Abs. 25, 4463z
(1971).
(154) "Collaborative Study of a Gas Chromatographic Method for the
Analysis of Diazinon", R. T. Murphy, et al., J. Assoc. Offic.
Anal. Chem. 1971, 54(3), 700-2; Chem. Abs. 75, 4459c (1971).
X
(155) "Development of a Diazinon-Degrading Bacterium in Paddy Water
After Repeated Applications of Diazinon", N. Sethunathan, et al.,
Can. J. Microbiol. 1971. 17(5), 699-702; Chem. Abs. 75, 4592r
(1971).
(156) "Routine Method for the Determination of Organophosphorus
Insecticides by Thin- Layer Chromatography" , 0. Antoine, et al.,
J. Chromatogr. 197 1» 58(2), 247-56; Chem. Abs. 25, 75234m (1971).
(157) "Esterase Inhibition Technique for the Detection of Organo-
phosphorus Pesticides on Thin- Layer Chromatograms", T. Stijve,
et al., Mitt. Geb. Leoensmittelunters. Hyg. 1971. 62(1), 25-31;
Chem. Abs. 25, H7195g (1971).
(158) "Infrared and Ultraviolet Spectra of Seventy-Six Pesticides",
R. C. Gore, et al., J. Assoc. Offic. Anal. Chem. 1971. 54(5),
1040-82; Chem. Abs. 25, 117202g (1971).
(159) "Biological Determination of the Active Principles of Some
Insecticides", M. Menezes, et al., Rev. Agr. (Sao Paulo)
1971. 46(1), 9-14; Chem. Abs. 21, 117460q (1971).
(160) "Thin- Layer Chromatographic Analysis of Organophosphate Pesticides
in the Study of Environmental Contamination (Italian Surface
Waters)", V. Leoni, et al. , Farmaco, Ed. Prat. 1971. 26(7),
383-93; Chem. Abs. 25, 128757t (1971).
(161) "0-2-Acetyl-6-Methylpyrimidin-4-yl-0,0-Diethyl phosphorothioate,
a new Degradation Product of Diazinon", A. F. Machin, et al.,
Chem. Ind. (London) 1971. (42), 1198-9; Chem. Abs. 2£» 42755z
(1972).
(162) "Electrolytic Conductivity Detection of Some Nitrogen-Containing
Herbicides", W. P. Cochrane, et al., J. Chromatogr. 1971. 63(2),
364-9; Chem. Abs. 7.6, 122725e (1972).
90
-------
(163) "Quantitative Thin-Layer Chromatography of Organothiophosphorus
Pesticides by in Situ Fluorimetry", R. W. Prei, et al., Int.
J. Environ. Anal. Chem. 1971. 1(2), 99-111; Chem. Abs. 76.
136670V (1972).
1972
(164) "The p-Value Approach to Quantitative Liquid-Liquid Extraction
of Pesticides From Water. I. Organophosphates. Choice of pH
and Solvent", I. H. Suffet, et al., J. Agr. Food Chem. 1972.
20(1), 52-6; Chem. Abs. 2§» 109005a (1972).
(165) "Analytical Studies on Pesticides and Related Compounds. XV.
Improved Determination of Several Organophosphorus Pesticides",
E. Yuki, et al., Buneski Kagaku.1972. 21(3), 375-8; Chem. Abs.
27, 44l49z (1972).
(166) "Increased Biological Hydrolysis of Diazinon After Repeated
Application in Rice Paddies", N. Sethunathan, et al., J. Agr.
Food Chem. 1972. 20(3), 586-9; Chem. Abs. 2Z» *4316b (1972).
(167) "Elution Solvent System for Florisil Column Cleanup in Organo-
chlorine Pesticide Residue Analyses", P. A. Mills, et al.,
J. Assoc. Offic. Anal. Chem. 1972. 5.5(1), 39-43; Chem. Abs.
27, 7113ly (1972).
(168) "Diazinon Degradation in Submerged Soil and Rice-Paddy Water",
N. Sethunathan, Advan. Chem. Ser. 1972. lll(Fate of Org. Pestic.
in the Aquatic Environ.), 244-55; Chem. Abs. 2Z» 148524j (1972),
(169) "Infrared Analysis of Pesticide Formulations", S. W. Goza, J.
Assoc. Offic. Anal. Chem. 1972. 55(5), 913-17; Chem. Abs. 2Z»
160898s (1972).
(170) "Intoxication Caused by Products Resulting From Diazinon
Degradation, and Their Use as a Tickicide", D. Mello, et al.,
Biologico 1972. 38(5), 136-9; Chem. Abs. 78, 12400d (1973).
(171) "Determination of Diazinon and Dursban in Animal Milk, Organs,
and Tissues Using Gas Chromatography", 6. A. Talanov, et al.,
Khim. Sel. Khoz, 1972. 10(11), 842-4; Chem. Abs. 28, 39096w
(1973).
(172) "Evaluation of the Pye Thermionic Detector", R. Greenhalgh,
et al., Column 1972. No. 14, 4-9; Chem. Abs. 78. 106838e
(1973).
(173) "Loss of Diazinon From Dacca Paddy Field Soils", A. I. Nasim,
et al., Pak, J. Sci. Ind. Res. 1972. 15(4-5), 330-2; Chem.
Abs. 22, 74887x (1973).
91
-------
(174) "Resistance of Insects to Insecticides", V. Rupee, Vesmir 1972,
51(12), 359-60; Chenu Abs. 79, 1184f (1973).
1973
(175) "Detection of Organophosphorus Pesticide Residues in Autopsy
Tissues by Thin-Layer Chromatography", S. N. Tewari, et al.,
Hikrochim. Acta 1973. (2), 321-4; Chem. Abs. 28, 93227c (1973).
(176) "Rapid Determination of the Organophosphorus Pesticides Diazinon
and Di Chlorvos in Blood by Gas Chromatography", A. F. Machin,
et al., Analyst (London) 1973. 98(1164), 176-80; Chem. Abs. 79,
907g (1973).
(177) "Insects Suitable for the Hicrobioassay of Insectides Residues",
S.S.H. Qadri, Pesticides 1973. 7(3), 22-3; Chem. Abs. 79, I4279r
(1973).
(178) "Basudin Detection Reactions", M. A. Tadzhiev, et al.,
Farmatsiya (Moscow) 1973. 22(2), 79-81; Chem. Abs. 79, 28211z
(1973).
(179) "Selective Gas Chromatographic Detector Using Ion-Selective
Membrane Electrode. III. Selective Detection of Nitrogen
Compounds Using a Cation-Sensitive Glass Electrode", T. Kojima,
et al., Bunseki Kagaku 1973. 22(2), 208-13; Chem. Abs. 79,
74739a (1973).
(180) "Isolation and Possible Significance of Some Toxic Mammalian
Metabolites of Diazinon", A. F. Machin, Pestic. Sci.i.1973,
4(3), 425-30; Chem. Abs. 79, 87995f (1973).
i
(181) "Reaction Gas Chromatographic Analysis of Pesticides. II.
On-Column Transesterification of Organophosphates by Methanol",
B. A. Moye, J. Agr. Food Chem. 1973. 21(4), 621-5; Chem. Abs.
79, 101510c (1973).
(182) "Detection of Organophosphorus Pesticides by in Situ Fluorometry
on Thin-Layer Chromatograms", G. L. Brun, et al., J. Chromatogr.
1973. 80(1), 117-23; Chem. Abs. 79, 112253x (1973).
(183) "Persistence of Biological Activity of Seven Insecticides in
Soil Assayed With Folsomia Candida", A. R. Thompson, J. Econ.
Entomol. 1973. 66(4), 855-7; Chem. Abs. 79, 112354f (1973).
(184) "Polarographic Determination of Sulfur in Some Sulfur-Containing
Pesticides", E. S. Kbsmatyi, et al., Zh. Anal. Khim. 1973. 28(5),
1028-9; Chem. Abs. 22» 122491n (1973).
92
-------
DICAMBA
1952
(1) "Alkali Hydrolysis of Chlorobenzenes. I. Hydrolysis of Dichloro-
benzenes With Methanolic Sodium Hydroxide", 0. Nobuto, et al.,
J. Soc. Org. Synthet. Chem. (Japan) 10, 295-7 (1952); Chem. Abs.
47, 5375b (1953). "~
(2) "Hydrolysis of Polychlorobenzenes and the Relative Hydrolysis
Velocity of Chlorobenzenes. Ibid. 297-300. 0. Nobuto, et al.,
Chem. Abs. 47, 5375c (1953).
(3) "Alkali Hydrolysis of Chlorobenzenes", 0. Nobuto, et al., Repts.
Govt. Chem. Ind. Research Inst. Tokyo", 47, 327-36 (1952); Chem.
Abs. 48, 9941e (1954). """
1955
(4) "Trichlorobenzene of Enhanced 1,2,4-Isomer Content", Columbia-
Southern Chemical Corp. U.S. 2,725,409, Nov. 29, 1955; Chem. Abs.
M., 3661g (1957).
1956
(5) "Chlorinated Benzenes from Waste Isomers of Hexachlorocyclohexane",
Commercial Solvents Corp. U.S. 2,742,508, Apr. 17, 1956; Chem.
Abs. 50, 16848h (1956).
(6) "Trichlorobenzenes from Crude Benzene Hexachloride", Olin Mathieson
Chemical Corp., U.S. 2,745,833, May 15, 1956; Chem. Abs. 50, 168481,
(1956).
(7) "Dehydrochlorination of Benzene Hexachloride", Ethyl Corp., U.S.
2,757,211, July 31, 1956; Chem. Abs. 51, 2858c (1957).
1957
(8) "Halogen Derivatives of Dibenzo-p-dioxin", H. Oilman, et al., J. Am.
Chem. Soc. 22» 1439-41 (1957); Chem. Abs. .51 10529d (1957).
(9) "Trichlorophenols from Tetrachlorobenzenes", Dow Chemical Co., U.S.
2,799,713, July 16, 1957; Chem. Abs. 52, 2070d (1958).
(10) "Hydrolysis of di- and trichlorobenzenes", Dow Chemical Co., U.S.
2,799,714, July 16, 1957; Chem. Abs. 52, 2070g (1958).
93
-------
1958
(11) "Antibacterial Compounds for Agricultural Use", Research Foundation
for Insecticidal Science, Japan. 8965 Oct. 9, 1958. Chem. Abs. 54,
ASOlg (1960).
1961
(12) "2-Methoxy-3,6-Dichlorobenzoic Acid as Herbicidal Composition",
Velsicol Chemical Corp., U.S. 3,013,054, Dec. 12, 1961; Chem. Abs.
56, 10049d (1962). '
*^^" i*
>•.. ,n ••>•.•
1962 , :
(13) "Compounds Having Herbicidal Activities", Velsicol Chemical Corp.
Brit. 901,553, July 18, 1962; Chem. Abs. .59, 13890g (1963).
1963
(14) "Chlorinated Diphenyl Oxides", S. A. Progil, Fr. 1,327,189, May 17,
1963; Chem. Abs. 59, I2709b (1963).
(15) "Herbicides", Velsicol Chemical Corp. Fr. 1,345,638, Dec. 13, 1963;
Chem. Abs. 60, 15784g (1964).
1964
(16) "Determination of Trichlorobenzene Isomers by Gas Chromatography",
J. Hrivnak, et al., Chem. Zvesti 18(9), 692-7 (1964); Chem. Abs. 61.,
15358f (1964). ,
1965
(17) "Thin-Layer Chromatographic Behavior of Compounds Effective as
Herbicides", H. 6. Henkel, Chimia (Aarau) 19(3), 128-31 (1965); Chem.
Abs. 62, 15358f (1965). t?i
(18) "Analysis of Dicamba in Crops and Milk, Including a Rapid^Cleanup
Method", M. Smith, et al., J. Assoc. Offie. Agr. Chemistsi48(6),
1164-9 (1965); Chem. Abs. 64, 7269h (1966).
(19) "2-Methoxy-3,6-Dichlorobenzoic Acid", Velsicol Chemical Corp.,
Neth. Appl. 6,506,607, Nov. 29. 1965; Chem. Abs. 65., 656h (1966).
. -«pu.
1966 f
(20) "Gas Chromatography of Phenoxyalkanecarboxylic Acids and Other
Herbicidal Acids", H. Henkel, J. Chromatog.^22(2), 446-9 (1966);
Chem. Abs. J&5, 6214c (1966).'
94
-------
(21) "Separation of Derivatives of 3,6-Dichloro-o-anisic and 3,6-
Dichlorosalicylic Acids and Their Acetic Homologs by Gas Chroma-
tography. M. Wilcox, Anal. Biochem. 1£(2), 253-9 (1966); Chem.
Abs. 65, 11231b (1966).
(22) "2-Methoxy-3,6-Dichlorobenzoic Acid", Velsicol Chemical Corp.,
Brit. 1,038,605, Aug. 10, 1966; Chem. Abs. 65, 16903g (1966).
1967
(23) "Separation of Alkyl and Trimethylsilyl Derivatives of Dicamba,
3,6-Dichloro-5-hydroxy-o-anisic Acid, and 3,6-Dichlorogentisic
Acid by Thin-Layer and Gas-Liquid Chromatography", B. R. Ray,
et al., J. Chromatog. 30(2), 428-32 (1967); Chem. Abs. 68, 21104f
(1968).
(24) "2-Methoxy-3,6-Dichloro-5-Aminobenzoic Acid", Velsicol Chemical
Corp., U.S. 3,345,157, Oct. 3, 1967; Chem. Abs. ,69, 18857u (1968).
1968
(25) "Collaborative Study of Infrared Analysis of Dicamba", M. Malina,
J. Assoc. Offie. Anal. Chem. 1968, 51(6), 1301-3; Chem. Abs. 22»
10528n (1969).
(26) "1,2,4,5-Tetrachlorobenzene Production", Hooker Chemical Corp.,
Fr. 1,527,361, May 31, 1968; Chem. Abs. 71, 60979b (1969).
1969
(27) "Dissipation and Phytotoxicity of Dicamba", R. R. Hahn, et al.,
Weed S'ci. 1969. 17(1), 3-8; Chem. Abs. 22. 56572a (1969).
(28) "2-Alkoxy-3,6-Dichlorobenzoic Acid Herbicides", Hooker Chemical
Corp., U.S. 3,444,192, May 13, 1969; Chem. Abs. 21» 38593z (1969).
(29) "Quantitative Analysis of Phenolic Saponification Products of
1,2,4-Tricholorbenzene After Gas or Thin-Layer Chromatographic
Separation", D. Ehrhardt, et al., Chem. Tech. (Leipzig) 1969,
21(7), 416-17 (Ger); Chem. Abs. 71,, 98108e (1969).
(30) "Direct Detection of lonizable Herbicides by Electrophoresis",
R. Purkayastha, Bull. Environ. Contam. Toxicol. 1969, 4(4),
246-55; Chem. Abs. n, 111684m (1969).
(31) "Isolation of 2,4-Dichlorophenol From an Isomeric Mixture",
C. H. Boehringer, Sohn, U.S. 3,462,498, Aug. 19, 1969; Chem. Abs.
21, 123924c (1969).
(32) "Dichlorophenols", Coalite and Chemical Products Ltd., Ger., Offen,
1,906,205, Aug. 14, 1969; Chem. Abs. 21» 123925d (1969).
95
-------
(33) "Thin-layer Chromatographic Determination of 2-Methoxy-3,6-
Dichlorobenzoic Acid", G. N. Dorofeenko, et al., lev. Timiryazev.
Sel'skokhoz. Akad. 1969, (5), 232-5; Chem. Abe. 72, 77683u (1970).
(34) "Jsomer Distribution on Substitution Reactions of Aromatic Com-
pounds. I. Isomer Distributions on Chlorinatlon of mono-, di-,
and trichlorobenzenes", S. Yamamoto, et al., Kagaku To Kogyo
(Osaka) L969 (Pub. 1971), 45(9), 456-60; Chem. Abs. 76, 99244m
(1972). ~~
1970
(35) "Rapid Esterification of Dlcamba and Chlorophenoxy Acids with
N,0-bis(trlmethylsilyl)acetamide for Gas Chromatographic Analysis",
T. P. Garbrecht, J. Assoc. Offic. Anal. Chem. 1970, 53(1), 70-3;
Chem. Abs. 72, 77684v (1970). •"""""
(36) "Report on Herbicides and Plant Growth Regulators", G. Yip, J.
Assoc. Offlc. Anal. Chan. 1970, 53(2), 358-60; Chem. Abs. J3,
65222a (1970).
(37) "Simultaneous Gas-Chromatographic Determination of 2,4-D [2,4-
dichlorophenoxyacetic Acid] and Dicamba in Human Blood and Urine",
J. B. Rivers, et al., J. Chromatogr. 1970, 50(2), 334-7; Chem.
Abs. 73. 86777a (1970).
(38) "Method for Determining 2-Methoxy-3,6-Dichlorobenzolc Acid in
Soil", M. Y. Berezoviskii, et al., Dokl. TSKHA (Timiryazev.
Sel'skokhoz. Akad) 1970, No. 160, 163-7; Chem. Abs. 74, 123873x
(1971).
(39) "Analysis of Chlorobenzenes by Gas Chromatography", R. W. Han,
et al., Choson Mlnjujuui Inmln Konghwaguk Kwahagwon Tongbo 1970,
No. 5, 39-41; Chem. Abs. .75, 104851t (1971).
(40) "Gas-Chromatographic Separation of the Components of Dianate",
B. S. Mramornov, et al., Nauch.'Konf., Posvyashch. 75-letiyu
Kafedry Gig. Tartu. Cos. Univ. 30-letiyu Tartu. Gor. SES (Sanit.-
Epidemiol. Sta.) 1970, 247-50; Chem. Abs. .76, 42537e (1972).
1971
(41) "Investigation of Flavones as Fluorogenic Spray Reagents for
Organic Compounds on a Cellulose Matrix. II. Detection of Pesti-
cides", V. Mallet, et al., J. Chromatogr. 1971, 56(1), 69-77;
Chem. Abs. 74, 123973e (1971).
(42) "Thin-Layer Chromatographic Procedure for the Detection in Soils
and Waters of Herbicide Residues Commonly Used in Saskatchewan",
A. E. Smith, et al., J. Chromatogr. 1971, 57(2), 303-8; Chem.
Abs. 25, 4307b (1971).
96
-------
(43) "Determination of Some Acidic Herbicides by Thin- Layer Chromato-
graphy", A. Guardigli, et al., J. Agr. Food Chem. 1971. 12(6),
1181-2; Chem. Abs. 2£, 1292p (1972).
(44) "Determination of 2-Methoxy-3,6-Dichlorobenzoic Acid in Plants by
Thin-Layer Chroma tography", M. Y. Berezovskii, et al., Khim. Sel.
Khoz. 1971. 9(4), 269-71; Chem. Abs. 22» 19052p (1971).
(45) "2-Hydroxy-3,6-Dichlorobenzoic Acid", U.S.S.R. 292,955 Jan. 15,
1971; Chem. Abs. 75, 3544 7b (1971).
(45a) "Determination of 2~Methoxy-3,6-Dichlorobenzoic Acid in Plants
by a Combined Method", M. S. Raskin, et al., Tr. Vses. Soveshch.
Issled. Ostatkov Pestits, Profil. Zagryazneni- ya Imi Prod.
Pitan. Kormov Vnesh. Sredy, 2nd 1971. 364-5; Chem. Abs. 28, 806 93 b
(1973).
(46) "Determination of 2-Methoxy-3,6-Dichlorobenzoic Acid by Gas-Liquid
Chroma tography", A. A. Ryzhkov, et al., Tr. Vses. Soveshch. Issled.
Ostatkov Pestits. Profil, Zagryazneni* ya Imi Prod. Pitan., Kormov
Vnesh. Sredy, 2nd 1971. 116-19; Chem. Abs. 78, 80694c (1973).
(47) "Carboxylstion of Chlorophenols with Carbon Tetrachloride in
Aqueous Caustic Alkaline Medium. Synthesis of Some Chlorohydroxy-
benzoic Acids and Their Derivatives. H* Suzuki, et al., Nippon
Kagaku Zasshi 1971. 92(11), 1002-5; Chem. Abs. 76_, 126536s (1972).
1972
(48) "Chemical and Thermal Aspects of Pesticide Disposal", M. V. Kennedy,
et al., J. Environ. Qual. 1972, 1(1), 63-5; Chem. Abs. 76. 69170s
(1972).
(49) "Preparation and Structure of 2,3,7,8-Tetrachlorodibenzo-p-
dloxin and 2,7-dichlorodibenzo-p-dioxin", F. P. Boer, et al.,
J. Amer. Chem. Soc. 1972, 94(3), 1006-7; Chem. Abs. 76, 91364e
(1972). "~~*
(50) "Analysis of Decomposition Products of Pesticides", M. V. Kennedy,
et al., J. Agr. Food Chem. 1972, 20(2), 341-3; Chem. Abs. 77,
1629p (1972).
(51) "Survey of Polychlorodibenzo-p-dioxin Content in Selected Pesti-
cides", E. A. Woolson, et al., J. Agr. Food Chem. 1972. 20(2),
351-4; Chem. Abs. 21, 1630g (1972). """"
(52) "Preparation and Characterization of Chlorinated Dibenzo-p-
Dioxlns", A. E. Pohland, et al., J. Agr. Food Chem. 1972 , 20(6),
1093-9; Chem. Abs. 78, 43387J (1973).
(53) "Mild Thermal Degradation of Pesticides", B. J. Stojanovic, et al.,
J. Environ. Qual. 1972, 1(4), 397-401; Chen. Abs. .78, 8 09 04 w
(1973). """"
|97
-------
(54) "Quantitative Analysis of Trichlorobenzenes by Gas Chromatography",
F. W. Karasek, J. Chromatogr. Sci. 1972, 10(9), 573-5; Chem. Abs.
79, 91699e (1973).
1973
(55) "3,6-Dichloro-2-methoxybenzoic Acid", Takeda Chemical Industries,
Ltd. Japan 7305,574 Feb. 17, 1973; Chem. Abs. j[8, 124295e (1973).
(56) "Determination of 2-methoxy-3,6-dichlorobenzoic Acid in Plants",
M. S. Raskin, Rhim. Sel. Khoz. 1973, 11(2), 130-3; Chem. Abs. 18,
132570f (1973).
(57) "Herbicidal Compositions", Balchem Corp. U.S. 3,725,031 Apr. 3,
1973, 7 pp; Chem. Abs. .79, 1356p (1973).
(58) "Catalytic Hydrolysis of 1,2,4-trichlorobenzene to 2,5-dichloro-
phenol", A. Malik, et al., Przem. Chem. 1973, 52(2), 99-102;
Chem. Abs. 79_ 17700g (1973).
(59) "Determination of 2-methoxy-3,6-Dichlorobenzoic Acid (Banvel D)
in Apples by Thin-Layer Chromatography", F. P. Vaintra* ub, et al.,
Gig. Sanit. 1973, (5), 79-81; Chem. Abs. 79, 39l90t (1973).
(60) "2-Methoxy-3,6-dichlorobenzoic Acid", U.S.S.R. 345,129, Apr. 17,
1973, From Otkrytiya, Izobret., Prom. Obraztsy, Tovarnye Znaki
1973, 50(18), 177-8; Chem. Abs. 79, 42l81w (1973).
(61) "Preparation of Chlorodibenzo-p-dioxins for lexicological Evalua-
tion", 0. Aniline, Advan. Chem. Ser. 1973. 120, 126-35; Chem. Abs.
79, 66268f (1973).
(62) "Transformation of Dicamba in Regina Heavy Clay", A. E. Smith,
J. Agr. Food Chem. 1973, 21(4), 708-10; Chem. Abs. 79 10157b
(1973)
98
-------
DIMETHOATE
1956
1. "Determination of Residues of 0,0-Dimethyl Dithiophospborylacetic
Acid N-Methylamide in Cherries Treated with Products Containing
This Pesticide", R. Santi et al., Chimica (Milan) 12, 325-8 (1956);
Chem. Abs.:51, 4632a (1955).
2. "Chemical and Biological Microdetermination of Residue of N-
monomethylamide of 0,0-Dimethyl Dithiophosphorylacetic Acid (L 395
in Olive Oil1.', B. Bazzi et al., Monograph; Chem. Abs. 51, 4632d (1955).
1957
3. "Alkylcarbamoylmethyl Dimethyl Phosphorodithioates", American Cyanamid
Co., U. S. Patent 2,996,531, Appl. July 1, 1957; Chem. Abs. 56,
332f (1962).
1958
4. "Chemical Determination of N-Methylamide of 0,0-dimethyl Dithio-
phosphorylacetic Acid Residues in Olive Oil", B. Bassi, et al.,
Olivicoltura 13, No. 4, 3-5 (1958); Chem. Abs. 52, 211691 (1958).
1959
5. "The Decomposition of the N-monomethyl Amide of 0,0-dimethyl
Dithiophosphorylacetic Acid. I. Decomposition of the Pure,
Crystalline Compound", R. Fontanelli et al., Rend. 1st. super, sunta
22, 32-47 (1959); Chem. Abs. 53, 16457h (1959).
6. "Mode of Action and Biological Properties of the S-(methylcarbamoyl)-
methyl 0,0-dimethyl Dithiophosphate", R. Santi, et al., Nature 183,
398 (1959); Chem. Abs. 53, 15144c (1959).
7. "Determination of Rogor in Olives and in Various Vegetables", B. Bazzi
1st. ricercheagrar.soc Montecatine Milano, Contirb.3,93-108(19590;
Chem. Abs. 55, 25083c (1961)
8. "Pesticides "Montecatini" Societa generale per I1Industrie minerarla
e. chlmica", Ger. Patent 1,060,659, July 2,1959;Chem. Abs 55,0775d (1961).
9. "0,0-Dimethyldlthiophosphorlc Acid "Montecatini" Societa generale per
I1Industrie mineraria e chlmica. Ital. Patent 596,747, Aug. 4, 1959).
Chem. Abs. 55, 18594c (1961).
10. N-Monomethylamlde of 0,0-diethyldlthiophosphoryl-Acetic Acid- "Montecatini"
Societa generale per 1*Industrie mineraria e chimica", Ital. Patent
599,091, Oct. 21, 1959; Chem. Abs 55, 20%lh (1961).
99
-------
1960
11. "Determination of 0,0-dimethyl S-(N-methylcarbamoylmethyl) Phos-
phorodithionate in Technical Roger and its Formulations", L. F.
Dupee, et al., Analyst 85, 177-84(1960); Chem. Abs 54, 25528g (1960).
12. "Residues of 0,0-dimethyl S-(N-4nethylcarbamoylmethyl)-Phosphoro-
thiolothionate (Dimethoate) in Sprayed Crops", E. D. Chilwell, et
al., J. Sci. Food Agr. 11, 400-7(1960); Chem. Abs 54,21518h (1960).
13. "0,0-Dialkyl S-carbamoylmethyl Fhosphorodithioates" U. S. Patent
2,959,608, Nov. 8, 1960; Chem. Abs. 55, 18594e (1961).
14. "N-Methylcarhamidomethyl-0,0-Diemthyldithiophosphate", N. N. Mel'nikov
et al., U.S.S.R. Patent 131,759, Sept. 20, 1960; Chem. Abs.55,
7297e (1961).
1961
15. "Thin-Layer Chromatographic Detection of Insecticides", J. Baeumler
et al., Helv. Chim. Acta., 44, 1162-4(1961); Chem. Abs. 56, 12036a
(1962).
16. "0,0-Dialkyl and S-(N-alkylcarbamoylmethyl)Fhosphorodithioates as
Insecticides and Miticides "Montecatini" Societa Generale per
I1Industrie Minerarie e Chimica. U. S. Patent 3,004,055; Chem. Abs.
56, 15369a (1962).
17. "Pesticides", H. J. Renner et al., Ger. (East) 21,728, Aug. 10, 1961;
Chem. Abs. 57, 8444e (1962).
18. "Nuclear Magnetic Resonance (N.M.R.) Studies of Organophosphorus
Compounds. III. MeOP and MeSP Groups", G. Mavel, et al., J. Chim.
Phys. 59, 762-71 (1962); Chem. Abs. 58, 2342e (1963).
1962
19. "Cygon Dimethoate-New, Versatile Insecticide", D. Goleman, Chem.
Specialities Mfrs. Assoc. Proc. Mid-Year Meeting 48, 149 (1962);
Chem. Abs. 57, 17130h (1962).
20. "Polarographic Determination of the Monomethylamide of 0,0-Dimethyl-
dithiophosphorylacetic Acid (Rogor)", F. Tafuri, Ric. Sci. Rend. Sez.
B 2, No. 1, 60-3(1962).; Chem. Abs. 57 . 17134f (1962).
21. "The Determination of Organic Phosphorus Insecticides", N. Faderl,
Mitt. Gebiete Lebenxm. Hyg. 53, 154-75(1962); Chem. Abs. 57, 17125e
(1962).
100
-------
1962
22. "Synthesis of the Monomethylamlde of (Dimethoxyphosphi.nothioylthio)
Acetic Acid", C. H. Boehringer Soh., Belg. Patent 619497, Dec. 28,
1962; Chem. Abs. 59, H274d (1963).
23. "S-(N-Alkylcarbamoylmethyl) 0,0-Dimethyl Dithiophosphates, American
Cyanamid Co., Brit. Patent 886,319, Jan. 3, 1962; Chem. Abs. 59.
455e (1963).
24. "0,0-Dimethy1dithiophosphoryl-N-Methylacetamide", Badische Amlin-
& Soda-Fabrik A.-G, Ger. Patent 1,139,829; Chem. Abs. 58, 7835f (1963).
25. "N-Monoalkylamides of 0,0-Dimethyldithiophosphorylacetic Acid",
"Montecatini" Societa Generale per 1*Industria Minerteria e Chimica,
U. S. Patent 3,032, 579, May 1, 1962; Chem. Abs. .59, 8601g (1963).
1963
26. "Thiophosphate. 0,0-Diethyl O-(p-nitrophenyl) Ihiophosphate. 0,0-
Dimethyldithiophosphorylacetic Acid N-MethylamideV, R. Pirisi, et
al., Rend. Seminario Fac. Sci. Univ. Cagliari 33, 81-102(1963);
Chem. Abs. 66, 18546 (J967).
27. "Biological and Chemical Properties of Dimethoate and Related
Derivatives", U. E. Brady, Jr., et al., J. Econ. Entomol. 56(4),
477-82 (1963); Chem. Abs. 59, 6926c (1963).
28. "Determination of 0,0-Dimethyl S-(N-Methylcarbamoylmethyl)Phosphoro-
thiolonate (Rogor) in the Technical Material and in Formulations by
Means of Chromatographic Separation on Paper, Elution, and Colorimetric
Estimation of the Active Material", B. Bassi, et al., 1st Ric. Agrar,
Soc. Montecatini Milano 1963; Chem. Abs. 63, 12188g (1963).
29. "Monoalkylamides of 0,0-Dialkyl Dithiophosphorylacetic Acid", Sumlmoto
Chemical Industry Co., Ltd., Belg. Patent 624,028, Feb. 14, 1963;
Chem. Abs. 12 (1963).
30. "A Substituted o>[0,0-Dialkyl Mono- and Dithiophosphoryl]-Carboxamides.,
A.-G. Farbenfabriken, Belg. Patent 633,306, Dec. 6, 1963; Chem. Abs.
61» 579c (1964).
31. "0,0-Dimethyldithiophosphorylacetic Acid N-Methylamide, "Montecatini"
Societa Generale per I1Industrie Mineraria Chimica, Fr. Patent,
1,342,565, Nov. 8, 1963; Chem. Abs. 60, 10556b (1964).
32. "0,0-Dimethyldithiophosphoryl-N-Methylacetamide.", Badische Amlin-&
Soda-Fabrik A.-G, Ger. Patent 1,144,712; Chem. Abs. 59, 5029a (1963).
33. "0,0-Dialkyldithiophosphoryl Fatty Acid Amides", C. H. Boehringer Sohn,
Ger. Patent 1,146,486, Apr. 4, 1963; Chem. Abs. 59, 8790g (1963).
34. "Organic Phosphates", Sumitomo Chemical Co., Ltd., Japan. Patent
16,873, Sept. 3, 1963); Chem. Abs. 60, 2767a (1964).
101
-------
1964
35. "The Detection of Organophosphorus Pesticides on Thin-Layer Chromato-
grams", P. J. Bunyan, Analyst 89 (1062), 614-18 (1964); Chem. Abs.
61 (1961).
36. "Determination of Some Organophosphorus Insecticides by Gas-Liquid
Partition Chromatography" M. Horiguchi, et al., Chem. Pharm. Bull.
(Tokyo) 12(11), 1315-19(1964); Chem. Abs. 62, 5823g (1965).
37. "Gas-Chromatographic and Colorimetric Measurement of Dimethoate
Residues", C. H. Van Middelem, et al., J. Agr. Food Chem. 12(2),
178 82(1964); Chem. Abs. 60, 11272 (1964).
38. "Cryoscopic Analysis of Organic Phosphate PesticidesrMalathion
Dimethoate, 0,0-Diethyl 0-(2-Pyrazinyl)Phosphorothioate, and
Phorate", R. J. Best et al., J. Agr. Food Chem. 12(6), 546-9 (1964);
Chem. Abs. 62, lOOld (1965).
39. "Measurement of Residues of Cygon Insecticide and its Oxygen Analog
by Total Phosphorus Determination After Isolation by Thin-Layer
Chromatography", W. A. Steller, et al., J. Assoc. Offic. Agr. Chemists
47 (4), 645-51(1964); Chem. Abs. 61, 11238c (1964).
40. "Dimethoate", G. L. Sutherland, Anal. Methods Pesticides Plant Growth
Regulators and Food Additives, G. Zweig, Editor, Academic 2, 171-181
(1964); Chem. Abs. 61, 11263e (1964).
41. "Unidemensional Multiple-Unidemensional, and Bidimensional Thin-
Layer Chromatographic Separation of Organophosphorus Insecticides
and Their Residues in Vegetable Oils", P. Melchiorri et al.,
Farmaco, (Pavia), Ed. Prat. 19(12), 610-27(1964); Chem. Abs. 62,
12369b (1965).
42. "Pesticide Residues. Use of an Aerograph Flame lonization Detector
as a Thermionic Detector. Application to Organophosphate Insecticide
Research", R. Mestres, et al., Trav. Soc. Pharm. Montpellier 24(4),
283-303(1964); Chem. Abs. 63, 13970d (1965).
43. "The Determination of Traces of Phosphoric Esters by Oscillographic
Polarography", P. Nagniot, Anal. Chim. Acta 31(2), 166-74(1964);
Chem. Abs. 61, 12563c (1964).
44. "Thin-Layer Chromatography of Organophosphorus Pesticides and Acids
on Microchromatoplates", C. W. Stanley, J. Chromatog. 16(3), 467-75
(1964); Chem. Abs. 65, 11090a (1965).
45. "Detection and Separation of the Most Important Organophosphorus
Pesticides by Thin-Layer Chromatography", M. Salame, J. Chromatog.
16(3), 476-80 (1%4); Chem. Abs. 62, 11090b (1965)
102
-------
46. "Comparison of Gas Chromatographic Sensitivities for Dimethoate and
its 0 Analog with Electron Affinity and Flame lonization Detectors",
B. J. Gudzinowicz, J. Gas. Chromatog. 2(10), 335-7(1964); Chem.
Abs. 62, 11124f (1965).
47. "The Effect of Storage Conditions on Changes in theToxiclty of
Phosphamide", A. S. Sedykh, et al., Khim. v Sel'sk. Khoz. 1964(2),
22-4; Chem. Abs. j61, 6307e, (1964).
48. "Detection of Some Pesticides in Biological Material Using Thin-
Layer Chromatography11, M. A. Klisenko, Khim. v. Sel'sk. Khoz.
1964(5), 21-3; Chem. Abs. 61, 12563d (1964).
49. "Synthesis of N'Methyl-0,0-Dimethyldithiophosphorylacetamide",
T. Ambrus, et al., Rev. Chim. (Bucharest) 15(7), 386-9(1964);
Chem. Abs. 62, 5187f (1965).
50. "Infrared Spectrophotometric Methods for the Determination of Some
Organophosphorus Insecticides", G. Stanescu, et al., Rev. Chim.
(Bucharest) 15(7), 416-19(1964); Chem. Abs. 62, 5826c (1965).
51. "Carbamoylmethyl Phosphorothioates", Fisons Pest Control Ltd.,
Brit. Patent 947,778, Jan. 29, 1964; Chem. Abs. 60, 10548e (1964).
52. "Nontoxic Insecticides'.' "Montecatini" Societa Generale per
I1Industrie Mineraria e Chimica, Ger. Patent 1,177,138, Sept. 3,
1964; Chem. Abs. 61, 14537h (1964).
53. "Dimethyl Dithiophosphorylacetic Acid Methylamide",Montecatini"
Societa Generale per 1*Industria Mineraria e Chimica. Ital. Patent
661,487, March 17, 1964; Chem. Abs. 62, 5193f (1965).
54. "0,0-Dimethyl S-Methylcarbamoylmethyl Dithiophosphate", Sumitomo
Chemical Co., Ltd., Japan. Patent 24,956, Nov. 6, 1964; Chem. Abs.
62, H689e (1965).
1965
55. "Determination of Organophosphorus Insecticide Residues Using the
Emission Spectrometric Detector:, C. A. Bache, et al., Anal. Chem.
37(12) 1477-80(1965); Chem. Abs. 64, 1288a (1966).
56. "Identification of Trace Amounts of Organophosphorus Pesticides by
Frustrated Multiple Internal Reflectance Spectroscopy", T. S.
Hermann, Appl. Spectry, 19(1), 10-14(1965); Chem. Abs. 62, 12387b
(1965).
57. "Use of Thin-Layer and Temperature Gas-Liquid Chromatography in the
Detection, Determination, and Identification of Organo-Phosphorus
Pesticide Residues", D. C. Abbott, et al., Proc. SAC (Soc. Anal.
Chem) Conf., Nottingham, Engl. 1965, 121-3; Chem. Abs. 65, 19210f
(1966).
103
-------
58. "Rogor (Dimethoate) Residues in Food Crops", P. Tonelli et al.,
Residue Rev. 11, 60-99(1965); Chem. Abs. 65, 2896g (1966).
59. "Analytical Determination of Dimethoate. I. Titrimetric Determination
of Dimethoate", F. Grimmer, et al., Z. Che. 5(6), 234-6(1965); Chem.
Abs. 6.3, 13970h (1965).
60. "Determination of 0,0-Dimethyldithiophosphorylacetic Acid N-Methyl-
amide in Technical Dimethoate and its Formulations", K. Mueller,
Z. Anal. Chem. 215(4), 253-9(1965); Chem. Abs. 64, 11794g (1976).
61. "Synthesis of %- or 32P-Labeled 0,0-Dimethyl S-(Methylcarbamoylmethyl)
Phosphorodithioate and the Chroma£ography of Related Compounds", T.
Uchida, Yakugaku Zasshi 85(7), 638-41(1965); Chem. Abs. 63, 9799d (1965).
62. "Systemic Insecticidal S-Alky Icarbamoy line thy 1 0,0-Dimethyl Phosphoro-
dithioates", American Cyanamid Co., U. S. Patent 3,210,242, Oct. 5,
1965; Chem. Abs. 63, 1790Ih (1965).
63. "0,0-Dialkyl Dithiophosphates Containing a Carboxamido Group" VEB
Elektrochemische Kombinat Butterfeld, Belg. Patent 656,340, March
16, 1965; Chem. Abs. 65, 2126b (1966).
1966
64. "Determination of Residues of Dimethoate With Multi-Band Ghromatophates",
D. C. Abbott, et al., Analyst 91 (1079), 94-7 (1966); Chem. Abs. 64,
20515h (1966).
65. "Gas Chromatographic Column for Pesticide Residue Analysis; Retention
Times and Response Data", J. A. Burke, et al., J. Assoc. Offic. Anal.
Chemists 49(2), 374-85 (1966); Chem. Abs. 65, 2894g (1966).
66. "Mass Spectra of Some Organophosphorus Pesticide Compounds", N. Damico,
J. Assoc. Offic. Anal. Chemists 49(5), 1027-45 (1966); Chem. Abs. 66,
1834k (1967).
67. "Residues and Decomposition Products of Dimethoate After Application to
Greenhouse Cucumbers", D. Kubel, et al, Nahrung 10(7), 611-17(1966);
Chem. Abs. 66, 45753b (1967).
68. "Analysis of Pesticides by Infrared Spectrometry. IV. Rapid Determination
of Dimethoate in Some Formulations by Infrared Spectrophotometry", N.
Oh, et al., Bunseki Kagaku 15(3), 284-5(1966); Chem. Abs. 65, 7931d (1966),
69. "Residue Analysis of Agricultural Chemicals. III. Electroncapture Gas
Chromatography of Various Pesticides", J. Kanazawa et al., Nippon Nogei
Kagaku Kaishi 40(4), 178-84 (1966); Chem. Abs. 65, 4571f (1966).
104
-------
70. "Gas Chromatographic Analysis of Pesticides. II. Gas Chromatographic
Determination of Organophosphorus Pesticides", T. Takehara, et al.,
Nippon Nogei Kagaku Kaishi 40(11), 394-400(1966); Chem. Abs. 66,
94159w (1967).
71. "Colofimetrie Determination of Organophosphorus Insecticides with
Palladium Chloride. M. Fujimoto, et al., Sankyo Kenkyusho Nempo
18, 144-8(1966); Chem. Abs. 66, 114892k (1967).
72. "Analytical Investigations of 0,0-Dimethyl S-(N-Methylcarbamoylmethyl
Phosphorodithoate (Dimethoate). II. Thin-Layer Chromatographic
Determination of Dimethoate in Formulations'.1, F. Grimmer et al., J.
Chromatog. 22(2), 316-22(1966); Chem. Abs. 65, H268d (1966).
73. "Metabolism and Determination of Dimethoate in Vegetable Products",
B. Brunette, Contrib. 1st. Ric. Agr., Milan 1966-1967, 9,33-42;
Chem. Abs. n* 7568u (1970).
74. "Determination of the Phosphamide Content of a Technical Product",
V. V. Voronkova. Khim. v Sel'sk. Khoz. 4(6), 451-4(1966); Chem. Abs.
65, 20775a (1966).
75. "Determination of Toxic Organophosphorus Compounds (Phosphamide and
Chlorophos) in Natural and Waste Waters?, Yu. Yu. Lur'e,Gig, Sanit.
31 (11), 52-4(1966); Chem. Abs. 66, 31848z (1967).
76. "0,0-Dialkyldithiophosphoryl Fatty Acid Amides", W. Kochmann, et al.,
Ger. (East) Patent 44,406, Jan. 4, 1966; Chem. Abs. .64 17423b (1966).
77. "Preparation of 0,0-Dimethyldithiophosphorylacetic Acid N-Methylamide",
W. Kochmann, et al., Ger. (East) Patent 49,605, Aug. 20, 1966; Chem.
Abs. 66, 10602j (1967).
1967
78. "The Gas-Chromatographic Determination of Organophosphorus Pesticides.
II. A Comparative Study of Hydrolysis Rates", J. H. Ruzicka, et al.,
J. Chromatogr. 31(1), 37-47(1967); Chem. Abs. 68, 2191r (1968).
79. "Direct Fluorescent Detection of Organothiophosphorus Pesticides and
Some of Their Sulfur-Containing Breakdown Products After Thin-Layer
Chromatography", M. H. Ragab, J. Ass. Offie. Anal. Chem. 50(5), 1088-98
(1967); Chem. Abs. 67, 99119p (1967).
80. "Detection and Determination of Organophosphorus Insectides by the
Schoenemann Reaction", K. Lohs, Z. Chem. 7(3), 106-7(1967); Chem.
Abs. 66, 104259v (1967).
81. "2,6-Dibromobenzoequinone-4-Chloroimide as a Reagent for Determination
of Dimethoate, Honoalkyl-Aryl-Phosphorothionates, and Some Organic
Sulfides", J.H.V. Stenersen, Bull. Envirom. Contain. Toxicol. 1967,
2(6), 364-71; Chem. Abs. 69, 2041n (1968).
105
-------
82. "Thin-Layer Chromatographic Separation Scheme for Insectidally Active
Phosphoric Acid Esters", J. A. Guth, Pflanzenschutzberichte 35(9-10),
129-43(1967); Chem. Abs. 67, 72784q (1967).
83. "Isolation and Detection of Phosphamide in Biological Material",
0. A. Alimkhanov, Farmatsiya (Moscow) 16(4), 63-4(1967); Chem. Abs.
67, 107615q (1967).
84. "Determining Pesticide Residues in Plant Material and Soil1.', S. S.
Kosmatyi, Zashch. Rast. (Kiev) 1967, No. 6, 122-36; Chem. Abs. 71,
12018r (1969).
85. "Separation and Identification of Some Organophosphate Insectides by
Thin-Layer Chromatography and Their Determination After Conversion
Into Orthophosphate", D. Pantovic, Hrana Isshrana, 1967, 8(11-12),
700-71; Chem. Abs. .69, 66429c (1968).
86. "Thiophosphates", American Cyanamid Co., U. S. Patent 3,309,432,
March 14, 1967; Chem. Abs. 66, H4911r (1967).
1968
87. "Rcommended Methods of Analysis of Pesticide Residues in Foods. The
Determination of Dimethoate Residues in Fruits and Vegetables",
D. C. Abbott, Analyst (london) 1968, 93(1112), 756-66; Chem. Abs.
20, 27685J (1969).
88. "Nuclear Magnetic Resonance Studies of Phosphorus(V) Pesticides. I.
Chemical Shifts of Protons as a Means of Identification of Pesticides",
H. Babad, et al., Anal. Chim. Acta 41(2), 259-68(1968); Chem. Abs.
68, 77181w (1968).
89. "Automated Analysis of Organophosphorus Insecticides by Wet Digestion-
Oxidation and Colorimetric Determination of the Derived Orthophosphate",
E. Ott et al., J. Ass. Offic. Anal. Chem. 1968, 51(3), 697-708;
Chem. Abs. 69, 9901b (1968).
90. "Thin-Layer Chromatography of Organophosphorus Insecticides with
Several Adsorbents and Ternary Solvent Systems", M. E. Getz, et al.,
J. Ass. Offic. Anal. Chem. 1968, 51(5), 1101-7; Chem. Abs. 69 (1968).
91. "High-Resolution N.M.R. Spectra of Pesticides. I. Organophosphorus
Pesticides", L. H. Keith, et al., J. Ass. Offic. Anal. Chem. 1968,
51(5), 1063-94; Chem. Abs. 69, 75849s (1968).
92. "Versatility of OV-17 Substrate for Gas Chromatography of Pesticides",
C. A. Basche, et al., J. Ass. Offic. Anal. Chem. 1968, 51(6) 1270-1;
Chem. Abs. 70, 27907h (1969).
93. "Thin-Layer Chromatographic-Enzymic Detection of Organophosphorus
Insecticides. Activation of Weak Esterase Inhibitors", H. Ackermann,
J. Chromatogr. 1968, 36-(3), 309-17; Chem. Abs. 69 (1968).
106
-------
94. "Use of Hydriodic Acid in the Detection of Pesticides After Thin-Layer
Chromatographyl', J. Askew et al., J. Chromatogr. 1968, 37(2), 369-72;
Chem. Abs. 70, 10572x (1969).
95. "Nuclear Magnetic Resonance Studies of Phosphorus (V) Pesticides. III.
Hydroylsis of Aliphatic Pesticides by Aqueous Solutions", M. C.
Goldberg, et al., U. S. Geol. Surv., Prof. Pap. 1968, No. 600-D,
20-3; Chem. Abs. 22,67155t (1969).
96. "The Use of Gas Chromatography with Electron Capture in the Analysis
of Organophosphate Pesticides", M. Salame, Ann. Biol. Clin. (Paris)
1968, 26(7-9), 1011-21; Chem. Abs. 69, 10528u (1968).
97. "Detection of Thio- and Dithiophosphoric Esters and Esterase Inhibitor
on Thin-Layer Chromatograms", H. Beitz, Z. Chem., 1968, 8(10), 387-8;
Chem. Abs. 70, 10612k (1969).
98. "Gas Chromatographic Determination of Rogor (Dimethoate) Residues in
Cattle Meat", G. Bassi, et al., Contrib., 1st. Ric. Agr., Milan
1968-1969 10, 26-30; Chem. Abs. .79, 16992s (1973).
99. "Microanalysis of Some Organophosphorus Pesticides by a Spectrophotometric
Method Using Safranine Reagent", K. Suzuki, et al., Bunscki Kagaku 1968,
17(10), 1279-83; Chem. Abs. 70, 27904e (1969).
100. "Qualitative Analysis of Synthetic Organic Pesticides by Spot Tests",
M. Kanda, et al., Nippon Hoigaku Zasshi 1968, (22(3), 229-51; Chem.
Abs. 72, 6572x (1970).
101. "Analysis of Mixed Drugs by Mass Spectrometry. X. Pesticide Analysis.
2. Analysis of Pesticides in Commercial Preparations", A. Tatematsu,
et al.,, Shitsuryo Bunseki 1968, 16(1), 23 9; Chem. Abs. 69, 75853p
(1968).
102. "Detection of Residual Phosphamide in Meat and Milk", T. G. Abbasov,
Veterinariya 1968, 45(5), 97-8; Chem. Abs. 69, 42829g (1968).
103. "Sensitivity of Biological and Thin-Layer Chromatographic Methods of
Determining Pesticide Residues", A. S. Sedykh, et al., Proc. Int. Congr.
Entomol. 13th 1968, 2, 277-8 (Russ); Chem. Abs. 79, 14282m (1973).
1969
104. "Pesticide Residues. Indoxyl Acetate Spray Reagent for Fluorogenie
Detection of Cholinesterase Inhibitors in Environmental Samples", R.
L. Schultzmann, et al., J. Ass. Offic. Anal. Chem. 1969, 52(1), 151-6;
Chem. Abs. 70, 56345d (1969).
107
-------
105. "Pesticide Residues. Recovery of 65 Organophosphorus Pesticides
From Fluorisil With A New Solvent-Elution System", H. G. Beckmann,
et al., J. Ass. Offic. Analy. Chem. 1969, 52(2), 286-93; Chem.
Abs. 70, 80520z (1969).
106. "Gas Chromatography of Organophosphorus Pesticides; Retention Times
and Response Data on Three Columns", R. R. Watts, J. Ass. Offic.
Anal. Chem. 1969, 52(3), 513-21; Chem. Abs. .71, 12019s (1969).
107. "Polyamide-Layer Chromatography of Organophosphorus Pesticides",
K. Nagasawa, et al., J. Chromatogr.1969, 39(3), 282-90; Chem. Abs.
.70, 114093h (1969).
108. "Gas-Liquid Chromatography of Pesticides on OV-17 Stationary Phase",
V. Leoni, et al., J. Chroma togr. 1969, 43(3), 388-91; Chem. Abs.
71, 116424m (1969).
109. "Thin-Layer Chromatographic-Enzymic Detection of Organophosphorus
Insecticides. Thin-Layer Chromatographic Behavior of Some Other
Insecticides", H. Ackermann, J. Chroma togr. 1969, 44(2), 414-18;
Chem. Abs. 72, 77910r (1970).
110. "Determination of Organophosphorus Pesticides in Water", G. Zweig;
Residue Rev. 1969, 26, 17-36; Chem. Abs. TL, 80107u (1969).
111. "Thin-Layer Chromatographic Detection of Pesticide Residues in. Fruit
and Vegetables", A. Gruene, et al., Riechst. Aromen, Koerperpflegm.
1969, 19(11), 494, 496, 498, 500; (12), 550-4; Chem. Abs. 72,
131197d (1970).
112. "Analysis of Chlorinated and Organic Phosphorus Pesticides by Gas
Chromatography", M. Kanda, et al., Nippon Hoigaku Zasshi 1969, 23(6),
477-80; Chem. Abs. 73, 65310c (1970).
113. "Variation in the Toxicity and 159 Value of Chlorophos, Trichloromethaphos
3. Methylnitrophos, and Phosphamide During Storage Under Different
Conditions", T. G. Abbasov, Tr., Vses. Nauch.-Issled. Vet. Sanit 1969,
34, 235-40; Chem. Abs. .78, 24953z (1973).
114. "Determination of Phosphamide in Forensic Chemical Examination",
0. A. Alimkhanov, et al., (USSR). Sb. Tr. Sud. Med. Sud. Khim. 1969,
No. 3, 425-30; Chem. Abs. 77, 84107r (1972).
115. "Thin-Layer Chromatography for Identification of Traces of Insecticides,
Halathion, Dimethoate, and Ethion, in Dilute Solution", R. Tomus,
Rev. Chim. (Bucharest) 1969, 20(4), 259-61; Chem. Abs. 71. 69571v (1969).
116. "Determination of Insecticides Based on Phosphoric Acid Esters by Means
of the Chemiluminescence of Luminol", K. Weber, et al., Acta Pharm.
Jugoslov. 1969, 19(2), 47-53 Chem. Abs. 72, 77835v (1970).
108
-------
1970
117. 'Modified Enzymic Detection Method for Thin-Layer Chrooatograms
of Pesticides", G. F. Ernst, et al., J. Chromatogr. 1970, 49(2),
325-8, Chem Abs. 73, 76024p (1970).
118. "Correlations Between Fhosphrous-31 NMR Chemical Shifts and
Structures of Some Organophosphorus Pesticides", T. Ross, et al.,
Anal. Chim. Acta 1970, 52(1), 139-41, Chem Abs. K, 31000g (1971).
119. "GLC [Gas-Liquid Chromatographic] Retention Times of Pesticides
and Metabolites Containing Phosphorus and Sulfur on Four Thermally
Stable Columns", M. C. Bowman, et al., J. Ass. Offic. Anal. Chem.
1970, 53(3), 499-508, Chem Abs. 73, 24179y (1970).
120. "Gas-Chromatographic Analysis of Organophosphorus Pesticides",
D. B. Girenko, et al., Gig. Sanit. 1970, 35(5), 77-9, Chem Abs. 73,
65305e (1970).
121. "Thin-Layer Chromatographic Determination of Phosphamide and
Butiphos in Cottonseed Oil", N. G. Popova, et al., Gig. Isloviyakh
Zharkogo Klimata 1970, 366-9, Chem Abs. 77. 18202s (1970).
122. "Use of Thin-Layer Chromatography for Determining 0.0-dimethyl-S-
(N-methylcarbamoylmethyl) Dithiophosphate (Phosphamide) in Plants",
E. S. Kosmatyi, Metody Anal. Pestits 1970, 49-54, Edited by Yu. S.
Lyalikov, Red.-Izd. Otd. Akad. Nauk. Mold. SSR: Kishinev, USSR,
Chem Abs. 76, 42543d (1970).
1971
123. "Sensitized Photodecomposition and Photosensitizer Activity of Pesti-
cide Chemicals Exposed to Sunlight on Silica Gel Chromatoplates",
G. W. Ivie, et al., J. Agr. Food Chem. 1971, 19(3), 405-9, Chem Abs.
75, 19168f (1971).
124. "Infrared and Ultraviolet Spectra of Seventy-Six Pesticides", C. Gore,
et al., J. Ass. Offic. Anal. Chem. 1971, 54(5), 1040-82, Chem Abs.
75, 117202g (1971).
125. Negative Ion Mass Spectra of Some Pesticidal Compounds", P. C. Rankin,
et al., J. Ass. Offic. Anal. Chem. 1971, 54(6), 1340-8, Chem Abs. 76,
69019z (1971).
126. 'ftethod for Confirmation of Organophosphorus Compounds at the Residue
Level", M. T. Shafik, et al., Bull. Environ. Contain. Toxicol. 1971,
6(1), 55-66, Chem Abs. 74, 124014e (1971).
127. "Routine Method for the Determination of Organophosphorus Insecti-
cides by Thin-Layer Chromatography", 0. Antoine, et al., J. Chromatogr,
1971, 58(2), 247-56, Chem Abs. 75, 75234m (1971).
109
-------
128. "Separation of Fifty Paetlcide* and Ralatad Compound! and Polychioro-
biphenyl* Into Four Groups by Silica Gel", V. Laoni, J. Chromatogr.
1971, 62(1), 63-71, Cham Abe. 2ft. 82034v (1971).
129. "Organophoaphorua Pesticides in Livan Thair Identification by Oaa-
Llquld Chromatography (GLC). A. Coutaellnie, at al., J. Forensic
Mad. 1971, 18(1), 11-14, Cham Aba. 2J, 47745k (1971).
130. "Preliminary Teat for Simultaneous Detection of Organophoaphorus and
Organochlorine Peaticidea in Blood and Viscera", A. Coutsalinis, at
al., J. Foreanic Mad. 1971, 18(1), 35-6, Cham Aba. 21 • 47746m (1971).
131. "Eaterase Inhibition Technique for the Detection of Organophoaphorua
Peaticides on Thin-Layer Chromatogratns", T. Stijve, et al., Mitt.
Geb. Lebenamltteluntera Hyg, 1971, 62(1), 25-31, Cham Aba. 75,
U7195g (1971).
132. "Simultaneous Gaa Chromatographic Determination of Chlorinated
Hydrocarbons and Organophoaphates in Plant Material", G. Becker,
Deut. Lebenam.-Rundach. 1971, 67(4), 125-6, Cham Aba. 21i 4460v (1971).
133. "Isolation and Identification of Bye-Irritating By-Producta of
Dlmethoete Synthesis", Klaus D. Wantel, et al., Z. Cham. 1971,
11(12), 461-2, Cham Aba. 24. 108826g (1971).
134. "Gaa Chromatographic Analyaia of Dimethoate and ita Phoaphorui Con-
taminations in the Technical Product and in EC Formulations", Mueller,
et al., Ghent. Tech. (Lelpcig) 1971, 23(3), 174-5, Chem Aba. 2$.
123977J (1971).
135. "Thin-Layer Chromatographic Analyaia of Organophoephate Featieldaa
in the Study of Environmental Contamination (Italian Surface Waters)",
V. Leonl, et el., Farmaco, Ed. Prat. 1971, 26(7), 383-93, Cham Aba.
2J, 128757t (1971).
136. "Analytical Studies on Peaticidaa and Related Compounds. VI", A.
Murano, et el., Bunaeki Kagaku 1971, 20(6), 665-72, Chen, Aba.,
25, 97502* (1971).
137. "Feralatence In Water of Some Phosphate Eater Pesticides", Nagy,
et al., Egaasaagtudomany 1971, 15(8uppl.), 65-73, dlmathoate [60-31-5],
Chem. Aba. 26» 55211u (1972).
138. "Volumetric Determination of the Systemic Insecticide Roger (dimethoata),"
P. Spacu, et al., An. Univ. Bucuraeti, Chim. 1971, 20(20), 45-9, Chem.
Aba., 22. 62439v (1973).
139. "Thin-Layer Chromatographic Micromethod of Determining Phoaphamide in
Fruits and Vegetables", T. I. Golubev, et al., Gig. Sanit. 1971,
36(10), 69-73, Chem. Aba. 2£> 12855q (1972).
110
-------
140. "Coloriiutric Method of Detecting Tract Amounts of Phoephamlda
In Vegetable Matter", V. A. Volkova, at al., Vop. Pitan. 1971,
30(3), 82-3, Cham. Aba. 2i/12853n (1972).
141. "Determination of Phoephamide in Cadavara by Thin"Leyer Chroma-
tography, B. B. Bydytnanov, Gig. Priroan, Tokaikol. Paatita. Klin.
Otravl. 1971, No. 9, 187-8, Cham. Aba. 7.8, 53525e (1973).
142. "Thin Layar Chromatographlc Damonatration of Organophoephorus
Peaticldaa With Pulvarliad and Built in Developera", D. Sargaava,
Khranit. Prom. 1971, 20(10), 30-3, Cham. Aba. 21* 153S2e (1972).
143. "Ralation Batwaan tha Signal of an Blactron-Captura Datactor and
tha Structure of Peatlcldaa," D. B. Oiranko, Tr. Vaaa. Soveehch.
laalad, Oetatkov Paatita. Profil. Zagryaananlya Iml Prod. Pitan.,
Kormov Vnaah, Brady, 2nd 1971, 54-6, Cham. Aba. 18, 106828b (1973).
144. "Datamination of Boma Organophoaphorua Paatlcldaa in tha Soil
During Thair Bimultanaoua Praaanca", B. 0. Moloahanova, at al.,
Tr. Vaaa. Bovaahah. laalad. Oatatkov Paatita. Profllakt.
Zagryainaniya Prod. Pitan., Kormov Vnaah. Brady. 2nd 1971, 177-8,
and Rogor [60-51-3], Cham. Aba. 2£» 53835t (1973).
143. "Chromatographic-polarographic Datarminatlon of Dimathoata in
Planti,"E. B. Koamatyl, at al., Tr. Vaaa. Sovaahch. laalad.,
Oatatkov Paatita. Profil. Zagryatanlya Imi Prod. Pitan. Kormov
Vnaah. Brady, 2nd 1971, 234-6, Cham. Aba. 2&> 93424q (1973).
146. "Sensitivity of Biological and Thin-Layer Chromatographlc
Determination of Peaticidea11, 0. N. Abelentaava, at al., Tr. Vaea.
Boveahch. laaled Oatatkov Peatite. Profllakt. Zagryainaniya Prod.
Pitan., Kormov Vnaeh. Bredy, 2nd 1971, 331-4 and phoaphamide
[60-51-5], Cham. Aba. 2I» 53834a (1973).
1972
147. "Oaa-Liquld Chromatographlc Method for the Determination of
Dimathoata and Dlmathoxon Residues in Plant and Animal Tlaauee,
Milk, and Eggs", W. A. Steller, et al., J. Aaa. Off. Anal. Cham.
1972, 55(6), 1280-7, Cham. Abe.78., 27997c (1973).
148. "Matallofluoreacant Indicators aa Spray Reaganta for the in aitu
Determination of Organophoaphorua Peaticidea on Thin-Layer
Chromatograma", T. P. Bidlaman, at al., Anal. Chim. Acta 1972,
60(1), 13-23, Cham. Aba. 22., 84271q (1972).
149. "pH-8enaitlva Fluoroganic Spray Reagenta. XI. Quantitative
Studies With Pesticides", R. W. frei, et al., Chromatographia
1972, 5(5), 296-300, dimethoate [60-51-5], Cham. Aba. 21. 84268u
(1972).
Ill
-------
150. "Evaluation of the Pye Thermionic Detector", R. Greenhalgh, et al.,
Column 1972, No. 14, 4-9, organophoaphorus insecticides and herbicides
dimethoate [60-51-5], Chem. Abs. 78, 106838e (1973).
151. "Chemical Hydrolysis of Some Organic Phosphorus and Carbamate
Pesticides in Aquatic Environments", D. Faust, et al., Environ. Lett.
1972, 3(3), 171-201, Chem. Abs. 77_, 110352p (1972).
152. "Determination of Some Pesticides in Environmental Materials by
Gas-Liquid Chromatography", D. G. Girenko, et al., Probl. Anal.
Khim. 1972, 2, 39-43, phosphamide [60-51-5], Chem. Abs. 79, 62444n
(1973).
153. "Analysis of Dimethoate", A. Somogyi, et al., Nehezvegyip. Kut.
Intez. Koxlem. 1972, 4, 131-42, Dimethoate [60-51-5], Chem. Abs.
77., 148326w (1972).
154. "Analytical Studies on Pesticides and Related Compounds. XV.
Improved Determination of Several Organophosphorus Pesticides,
F. Yuki, et al., Bunseki Kagaku 1972, 21(3), 375-8, dimethoate
[60-51-5], Chem. Abs. 77^ 41149z (1972).
1973
155. "Persistence, Mobility, and Degradation of Carbon-14-Labeled-
Dimethoate in Soils", W. G. Duff, et al., Environ. Entomol. 1973,
2(3), 309-18, dimethoxon [1113-02-6], Chem. Abs. 79_, 74880q (1973).
156. "Determination of Pesticide Residues in Bee Honey. 1. Semi-
quantitative Thin-Layer Chromatographic Determination of Insecticide
in Bee Honey", B. Mueller, Nahrung 1973, 17(3), 381-6, Chem. Abs.
79, 144934m (1973).
157. "Determination of Some Phosphorus-Containing Pharmaceuticals by
Combustion in Oxygen", M. D. Kofman, et al., Farm. Zh. (Kiev)
1973, 28(2), 45-7, phosphamide, Chem. Abs. 79_, 35198d (1973).
158. "Mass-Spectrometric Analysis of Phosphamide", V. G. Manusadzhyan,
Arm. Khim. Zh. 1973, 26(1), 70-1, Chem. Abs. 79., 9957f (1973).
112
-------
DINOSEB
1944
(1) "Insecticide and Fungicide11, The Dow Chemical Co., U. S. 2,365,056,
Dec. 12, 1944; Chem. Abs. 39, 4428, 3 (1945).
1945
(2) "Alkyl Phenols", Sharp & Dohme, Inc., U. S. 2,391,798, Dec. 25,
1945; Chem. Abs. 40, 1971,9 (1971).
1946
(3) "Herbicides", Dow Chemical Co., U. S. 2,392,859, Jan. 15, 1946;
Chem. Abs. 40, 2263, 7 (1946).
1951
(4) "o-Alkylphenols and 2,4-dinitro-6-alkylphenols", Pest Control Ltd.,
Brit. 650,000, Mar. 7, 1951; Chem. Abs. 45, 956Ih (1951).
(5) "Characterization of Dinitroalkylphenols", 6. 6. S. Dutton, et al.,
Can. J. Chem. 31, 685-7(1953); Chem. Abs. 48, 8752d (1954).
1956
(6) "Crop Protection-Products-Approval Scheme. IV. Analysis of Dinoseb
and MCPA Weed-Killers", K. Gardner, J. Sci. Food Agr. ^,8 11(1956);
Chem. Abs. 50, 52201 (1956).
(7) "Determination of 4,6-dinitro-o-cresol, 4,6-dinitro-o-sec-butylphenol,
and 4,6-dinitro-o-isopropylphenol", Z. Anal. Chem. 148, 403-12(1956);
Chem. Abs. 50, 6738e (1956).
(8) "A Colorimetric Method for the Determination of Dinitrophenols",
Acad. Rep. Populare Romine, Studii Cericlari Chim. 4, No. 1-2, 93-8
(1956); Chem. Abs. 50, 165641 (1956). *"
(9) "The Chromatographic Determination of 4,6-dinitro-2-sec-butylphenol
in Weed-Killing Material", W.C.E. Bouwman, Chem. Weekblad 52, 827
(1956); Chem. Abs. ,51, 5345h (1957). *""
1957
(10) "Nuclear Alkylation of Aromatic Compounds Containing a Hydroxy Group",
A-G Bayer Farbenfabriken, Brit. 776,204, June 5, 1957; Chem. Abs. 52,
1257g (1958).
113
-------
(11) "Synthesis of Alkylphenols", A. G. Belorossova, et al., Uchenye
Zapiski Yaroslav Tekhnol. Inst. 2, 21-32 (1957); Chem. Abs. 53,
19940g (1959). "~ ~~
(12) "Collaborative Analytical Work on Mercury, Dinoseb, and MCPA",
R. de Brath Ashworth. Proc. Intern. Congr.Crop Protect., 4th, Hamburg,
1957 _2, 1129-32(Pub. 1960); Chem. Abs. 55, 2985b (1961).
1958
(13) "Determination of m-Dinitrophenyl Pesticides", C. Menzie, J. Agr.
Food Chem. £, 212-13 (1958); Chem. Abs. 52, 14947a (1958).
(14) "Alkylation of Phenols", Ethyl Corp., U.S. 2,831,898, Apr. 22,
1958; Chem. Abs. 52, 16293a (1958).
(15) "Uncatalyzed Thermal Ortho-Alkylation of Phenols" E. A. Goldsmith,
J. Org. Chem. 23., 1871-6(1958); Chem. Abs. 53, 10093i (1959).
(16) "Herbicidal Compositions Containing 2,4-dinitro-6-alkyl-phenols",
Dow Chemical Co., U.S. 2,841,483, July 1, 1958; Chem. Abs. 53,
10651J (1959).
(17) "Herbicidal Compositions Containing 2,4-dinitro-6-alkyl-phenols",
Dow Chemical Co., U.S. 2,841,482, July 1, 1958; Chem. Abs. 54,
6019e (1960).
(18) "The Contact-Catalytic Conversion of the Simple Phenolic Esters",
N.I. Shuikin, et al., Novye Metody Ratsional. Ispol'z, Trudy
Soveshchaniya, Riga 1958, 277-84(Pub. 1959); Chem. Abs. 56,
3390d (1962).
1959
(19) "Alkylation of Phenol by Olefins in the Presence of Boron Trifluoride
Dihydrate Synthesis of Propyl-, Butyl-, and Amy1-Phenol", L. A.
Gilyarovskaya, Izvest. Vysshikh Ucheb. Zavedenii, Neft i Gaz 1959,
No. 8, 63-9; Chem. Abs. 54, 4441f (1960).
1960
(20) "Synthesis of Alkyphenols From Borates by the Friedel-Crafts Reaction",
B. M. Sheiman, et al., Izvest. Vysshikh Ucheb. Zavedenii, Khim. i
Khim. Tekhnol.^3, 876-80(1960); Chem. Abs. 55, 9820a (1961).
1961
(21) "Comparison of Colorimetric and Polarographic Methods of Determining
Trace Amounts of Organic Nitro Insecticides, Fungicides, and
Herbicides", P. H. Martens, et al., Proc., 13th Internal:. Symp.
Phytofarm. Phytiatrie (Gent) 1961. 1523-9; Chem. Abs. 62, 1025d (1965).
114
-------
1962
(22) "Systematic Qualitative Analysis of Commercial Insecticides. II.
Analysis of Dinitro Preparations'.', Y. Otsubo, Kagaku Keisatsu-
Kenkyusho HokokuJLS, 226-31(1962); Chem. Abs. 57, 14229g (1962).
(23) 'b^Alkyl Phenols", A.-G. B. Farbenfabriken, Belg. 612,901, Feb.
15, 1962; Chem. Abs. 57, 13683h (1962).
(24) "Dinitrobutylphenol", E. Francais, Fr. 1,294,254, May 25, 1962;
Chem. Abs. .57, 16494g (1962).
1963
(25) "Alkylphenols", A.-G. B. Farbenfabriken, Ger. 1,142,873, Jan. 31,
1963; Chem. Abs. 58, 12468g (1963).
(26) "Alkylated Aromatic Hydroxy Compounds", A.-G.B. Farbenfabriken,
Brit. 918,053, Feb. 13, 1963; Chem. Abs. .59, 1535h (1963).
(27) "The Determination of Dinoseb in Potatoes", J. A. Potter, Analyst
£8(1049), 651-3(1963); Chem. Abs. 59, 1361e (1963).
(28) "Polarographic Determination of Dinitro-o-Cresol in Biological
Media", G. A. Khokhol'kova, Gigiena i Fiziol. Truda, Proizv.
Toksikol. Klinika Profzabolevanii, Sb. 2, 343-5(1963); Chem.
Abs. 63, 11981e (1965). ""
1964
(29) "Wedge-Layer Chromatography for Pesticide Residue Clean-up',' D. C.
Abbott, et al., Chem. Ind. 1964(12), 481; Chem. Abs. 60, 13811g
(1964). """"
(30) "Procedures for Residues of Dinitro Compounds", H. M. Boggs, J.
Assoc. Offic. Agr. Chemists, 47(2), 346-8(1964); Chem. Abs. £1,
2388e (1964).
(31) "Application of Polarography to Some Problems in Toxicology, I.
Detection and Estimation of m-Dinitrophenyl Type of Pesticides
in Biological Material", G. Gimbura, et al., Proc. Can. Soc.
Forensic Sci..2(2), 350 6(1964); Chem. Abs. 61, 7630i (1964).
(32) "Chromatographic Detection of Nitro Aromatic Herbicides in Toxi-
eoligical Analysis", M. Henneberg, Acta Polon. Pharm. 21(3),
296,302(1964); Chem. Abs. 62, 16865c (1965).
1965
(33) "Polarographic Determination of Various Dinitrophenols", C.
lonescu, Farmacia (Bucharest) 13(2), 95-100 (1965); Chem. Abs.
63, 2389b (1965).
115
-------
(34) "Selective Ortho Alkylation of Phenols", Koppers Co., Inc., Fr.
1,407,380, July 30, 1965; Chem. Abe. 63, 16261f (1965).
(35) "Extraction p-Values of Pesticides and Related Compounds in Six
Binary Solvent Systems", M. C. Bowman, et al., J. Assoc. Offic.
Agr. Chemists 48(5), 943-52(1965); Chem. Abs. 64, 4192h (1966).
(36) "Gas Chromatographic Determination of Phenolic Pesticides and
Residues", W. H. Gutenmann, et al., J. Assoc. Offic. Agr. Chemists
48(6), 1173-6 (1965); Chem. Abs. 64, 7270c (1966).
(37) '^-sec-Alkynitrophenols", Czech. 114,594, May 15, 1965; Chem. Abs.
64 15797d (1966).
1966
(38) "4,6-Dinitro-2-sec-Butylphenol (Butaphene)", U.S.S.R. 178,388,
Jan. 22, 1966; Chem. Abs. 64, 19490f (1966).
(39) "Determination of Phenoxyacetic Herbicide Residues in Biological
Materials", K. Erne, Acta Vet. Scand. 7(1), 77-96(1966); Chem.
Abs. 65, 7803g (1966). ""
(40) "Thin-Layer Chromatography of Dinitrophenol Pesticides", G. Yip,
et al., J. Ass. Offic. Anal. Chem. 49(6), 1166-9(1966); Chem.
Abs. 66, 45747c (1967).
(41) "Nitration of Substituted Phenols", E. Francais, Fr. 1,452,911,
Sept. 16, 1966; Chem. Abs. 66, 104812v (1967).
(42) "0-(sec-butyl)Phenol as Intermediate for the Manufacture of the
Herbicide Butaphen(2,4-dinitro-6-sec-butylphenol)", U.S.S.R.
184,872; Chem. Abs. 67, 21643k (1967).
(43) "Gas Chromatographic Determination of 2-sec-butyl-4,6-Dinitrophenol
in Pesticide Formulations", J. Hrivnak", Proc. Conf. Appl. Phys.-
Chem. Anal., Budapest, 1966,^2, 189-97; Chem. Abs. 68, 38459y (1968).
1967
(44) "Determination of 4,6-dinitro-0-(sec-butyl)Phenol Residues in Fruits
and Almonds by Electron-Capture Gas Chromatography", R. White,
et al., J. Food Sci. 32(6), 691-4(1967); Chem. Abs. 68, 67881k (1968).
(45) "Determination of Dinitrophenol Derivatives in Surface Waters", H.
Greger, Igiena (Bucharest) 1967, 16(10), 617-18; Chem. Abs. 69,
18205e (1968).
(46) "DNBP [2-sec-butyl-4,6-Dinitrophenol]", J.R. Lane , Anal. Methods
Pestic., Plant Growth Regul., Food Additives 1967. 5, 385-96;
Chem. Abs. 70 56497e (1969).
116
-------
(47) "Determination of Dinoseb in the Onion", L. A. Stempkovskaya,
et al., Rats. Pitan, 1967. 15-20; Chem. Abs. 70, 105202r (1969).
1968
(48) "Extraction and Cleanup Procedure for the Gas Chromatographic
Determination of Four Dinitrophenolic Pesticides", 6. Yip, J.
Ass. Offic. Anal. Chem. 51(1), 24-8 (1968); Chem. Abs. 68,
38223s (1968).
(49) "Gas Chromatography of Free Phenolic Pesticides", J. Hrivnak, J.
Gas Chromatogr. 6/1), 9-10 (1968); Chem. Abs. 68, 58669v (1968).
(50) "2-Alkylphenols and 2,6-Dialkylphenols", Ethyl Corp. U. S.
3,367,981, Feb. 6, 1968; Chem. Abs. 69, 51823c (1968).
(51) "Versatility of OV-17 Substrate for Gas Chromatography of
Pesticides", C. A. Bache, J. Ass. Offic. Anal. Chem. 1968. £1(6),
1270-1; Chem. Abs. 70, 27907h (1969).
(52) 'b-sec-Butylphenol", Romania, Ministry of the Chemical Industry,
Rom. 51,093, July 29, 1968; Chem. Ahs. 70, 57400e (1969).
(53) "Alkylation of Phenols", U. S. 3,418,379, Dec. 24, 1968; Chem.
Abs. 70, 67892f (1969).
(54) "Colorimetric Method for Determining Dinoseb in Foods, L. A.
Stempkovskaya, Vop. Ratsion, Pitan. 1968, No. 4, 168-74; Chem.
Abs. 21, 48392x (1969).
(55) "Detection of 4,6-Dinitro-o-Cresol (DNOC) and 4,6-Dinitro-Secobutyl-
phenol DNBP) in Biological Material by Paper Chromatography", B.
Mikolajczak, Zesz. Nauk, Wyzsz. Szk. Roln. Wroclawiu, Wet, 1968,
(24), 95-104; Chem. Abs. 72, 51630z (1970).
1969
(56) "Alkylphenols", Arakawa Forest Chemical Industries, Ltd., Japan
68,00,053, Jan. 6, 1969; Chem. Abs. 29.» 77575u (1969).
(57) "Chemical and Thermal Methods for Disposal of Pesticides", M. V.
Kennedy, Residue Rev. 1969. 29-89-104; Chem. Abs. 72, 53996x (1970),
(58) "Gas Chromatography of Alkyldinitrophenols and the Corresponding
Anisoles", D. R. Clifford, et al., J. Chromatogr. 1970. 48(3),
523-5; Chem. Abs. 73, 41608e (1970).
117
-------
1970
(3V) "Demonstration and Determination of Acidic and Phenolic Herbicide
Residues in Plant Material", H. P. Thleer, Dou. Ubanim.-Rundsoh,
1970. 66(11), 393-Bi Cham. Abi. 24. 3231c (1971).
(60) "Isolation of 2,4-Dinltro-6-aec-ButylphanolM, Ciaoh. 194,668,
Jan. 15, 1977; Cham. Aba. 2£, S3269d (1971).
1971
(t»i) "investigation of Plavonea ai Fluorgenie Spray Reagents for
Organic Compound! on a Galluloio Matrix. II. Dataotlon of Paaticidaa",
V. Mallet, J, Chromatogr. 1971. 56(1), 69-77; Cham. Aba. 74, 123973e
(1971).
(62) "Sensitised Photodeoomposition and Photosensitiaer Activity of
Pesticide Charaioaii Bxpoaed to Sunlight on Silica Oal Chromatoplatai",
G. W. Ivie, J. Agr. Food Cham. 197}. 19(3), 405-9; Cham. Abi, 21.
19l6Mt (1971).
(63) "Detection of Nitrophanol Pattioldaa on Thin-Layer ChromitograinaV,
A. M. Ihmigldlna, Qig. Sanit. 1971. 36(9), 77-8} Cham. Abi. 24.
10952v (1972).
(64) "Samiquantitatlve, Thin-Layer Chromatographto Determination of
DNOC and DNQP Rail due- In Plant and Soil11, P, Oruebner, Arch.
PfUnaentohuti, 1971. 7(4), 309-14; Cham. Aba. 10900lw, (1972).
(65) "Determination of Some Acidic Herbieidea by Thin-Layer Chromatography",
A. Quardigli, J. Agr. Pood Chen. 1971, 19(6), 1181-2} Chen. Abi.
2£, 12926p (1972).
(66) PetticIda1 Water-Soluble Dinltrophenolatei", Caeoh. 141,759, June
IS 1971; Chem. Aba. ]£, 61564y (1972).
^972
(i>7) "Chemical and Thermal Aapecta of Peatieide Dlipotal", M. V. Kennedy
et «!.. J. Environ. Qual. 1972. 1(1), 63-5; Chem. Aba., 2&» 69170a
(1972).
(68) "Meehaniam of the Rearrangement of Alkyl Phenyl Bthera. Aluminum
Chloride-Catalyaed Rearrangement of Butyl and sac-Butyl Phenyl Ethan",
P. A. Spannlngor, J, Aner. Chem. Soc. 1972. 94(6), 1970-3; Chen.
Aba. 2&. 126516k (1972).
(69) "Catalytic Preparation of o-Alkylatad Phenols", Pearson, William,
Ltd., Brit. 1,265,152. Mar. 1968; Chen. Aba. 2£. U330b (1972).
(70) "Analysis of Decomposition Products of Pesticides", M. V. Kennedy,
J. Agr. Food Chem. \972. 20(2), 341-3; Cham. Aba. 22, 1629p (1972).
118
-------
(71) "Infrarad Analyaia of Paaticida Pornulationa", 8. W. Goaa, J, Aaa.
Off. Anal, Chan, IfcTj, 33(3), 913-17} Chan. Aba. 22* 160898a (1972).
(72) 'Wlkyiphanoia", Sumitomo Ghanloal Go., Ltd., Japan, Kokal 72 31,938,
Nov. 14, 1972 i Cham. Aba. Ifi, 29422k (1973).
(73) "2,4-Dinitrophanoli", Beat Francaia, Oar. Of fan. 2,212,848, Nov.
30, 1972{ Chan. Aba. Ifl, 38033a (1973).
(74) "Charaioai and Tharnal Aapaota of Paatioida Diapoaal1,1 M. V. Karaiady,
at al., J, Bnviron, Qual. 1972. 1(1) « 63-3{ Cham. Aba. j£, 69170.
(1972).
(73) "Diract Nitration of Aikyphanoia with Nitric Acid", Dow Cham leal Co.
U, fl. 3,694,313, lapt. 26, 1972| Cham. Aba. 2fl. 71672. (1973).
(76) "Mild Thermal Dafradation of Paatioidaa", B. J. Stojanovio, J.
Bnviron. Qual. 1972. 1(4), 397-401; Cham. Aba. Ifl, 80904w (1973).
127J
(77) "laomeriaation of n-Alkyl Fhanyl Bthart in the Praaanoa of Boron
Trifluorida at Slavattd Praaauraa", L. M. Koalova, Latv. P8R
Zinat. Akad. Vaatia, Kim. Sar. 1973. (3), 319-23; Chan. Aba. 2fl,
76282U (1973).
(78) "Nitrating Phanola", Haroulaa, Inc. Oar, Of fan. 2,231,157, Jan. 11,
1973; Cham. Aba. Ifi, 110883k (1973).
(79) "Bubatitutad Fhanol Nitration", Ethyl Corp., U. 8. 3,733,838,
Aug. 1973 i Cham, Aba. 12, 104933d (1973).
(80) "Phanol Alkylation", Bthyl Corp., U. 8. 3,766,276, Oot. 16, 1973)
Cham. Aba, 22* I46196w (1973).
119
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FENSULFOTHION
1959
(1) "Thiophosphoric Acid Esters", Farbenfabriken Bayer Akt.-Ges.
Brit. 819,689, Sept. 9, 1959; Chem. Abs. 55, 11751g (1961).
(2) "Contact and Systemic Insecticidal Properties of 0,0-Diethyl
0-(p-Methylsulfinylphenyl)phosphorothionate and its Analogs",
E, Benjamini, et al., J. Econ. Entomol. 52, 99-102 (1959);
Chem. Abs. 55, 16895b (1961).
(3) "The Chemistry and Mode of Action of the Insecticide 0,0*
Diethy1 O-(p-Methylsulfinylphenyl) Phosphorothionate and its
Analogs", E. Benjamim, et al., J. Econ. Entomol. 52. 94-8
(1959); Chem. Abs. 55, 20303a (1961).
1960
(4) "Arylalkyl Ihioethers", Farbenfabriken Bayer Akt.-Ges. U.S.
2,923-743, Feb. 2, 1960; Chem. Abs. 54, 9849d (1960).
(5) "Aromatic Aliphatic Thioethere", Farbenfabriken Bayer Akt.-Ges.
Ger. 1,088^980, Sept. 15, 1960; Chem. Abs. 55, 25863b (1961).
1961
(6) "Thiophosphoric and Thiophosphonic Acid Esters", Farbenfabriken
Bayer A.-G. Brit. 866,4222, Apr. 26, 1961; Chem. Abs. 57.
13805a (1962).
1965
(7) "Nematocides", Farbenfabriken Bayer A.-G., Belg. 666,012, Oct. 18,
1965; Chem. Abs. 64, 20555f (1966).
1971
(8) Toxicology of Terracur P Active Ingredient", E. Loeser, et al.,
Pflanzenschultz-Nachr. (Amer. Ed.) 1971. 24(3), 407-30; Chem.
Abs. 29, 143245a (1973).
1973
(9) "Dasanit", C. A. Anderson, Anal. Methods Pestic. Plant Growth
Regul. 1973. 7, 253-68; Chem. Abs. 80, 104702y (1974).
120
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FENTHION
1959
(1) "New Phosphoric Ester Residual Insecticide With a Low Order of Toxicity",
H. F. Jung, et al., Bull. World Health Organization £1, 215-21(1959);
Chem. Abs. 54, 16728g (1960).
(2) "Thiophosphoric Acid Esters", A.-G. B. Farbenfabriken, Brit. 819,689,
Sept. 9, 1959; Chem. Abs. 55 11752h (1961).
1961
(3) "Thionophosphoric Acid Esters", A.-G. B. Farbenfabriken, et al.,
Ger. 1,116,656, Nov. 9, 1961; Chem. Abs. 56, 14170f (1962).
(4) "Toxicological Detection and Determination of Thiophosphoric Acid
Esters. II.", R, Fischer, et al., Pflanzenschutz, Ber. 27, 165-76
(1961); Chem. Abs. 59, 5677e (1963).
1962
(5a) "The Insecticide Residues from the Control of Rhagoletic Cerasi with
Che Organophosphorus Insecticide Lebaycid", H. M. Bode, Anz.
Schaedlingskunde 3J, 49-53(1962); Chem. Abs. 57. 7671f (1963).
(5) "Method of Determining Residues of the Insecticide Lebaycid in Plant
Material:, H. Frehse, et al., Pflanzenschutz Nachr. Bayer 15, 148-59
(1962-63) 3433d (1960).
(6) "Paper-Chromatographic Separation of Aromatic Phosphoric Ester
Insecticides1.1, H. Niessen, et al., J. Chromato. .9, 111-13(1962);
Chem. Abs. 58, 4986f (1963).
(7) "The Insecticide Residues from the Control of Rhagoletis Cerasi with
the Organophosphorus Insecticide Lebaycid", H.Maier-Bode, Anz.
Schaedlingsckunde 35, 49-53(1962); Chem. Abs. 57, 7671f (1962).
(8) "Method of Determining Residues of„the Insecticide Lebaycid in Olives
and Olive Oil", H. Frehse, et al., Pflanzenschutz-Nachrichten,
"Bayer", 15, 160-5(1962-3); Chem. Abs. 60, 11273c (1964).
1963 -
(9) "Stable Thiophosphate and Thiophosphite Composition", Chemagro Corp.,
U. S. 3,089,807, May 14, 1963; Chem. Abs. 63, 9259b (1%3).
(10) "Persistence of Mosquito Larvicides in Water", M. S. Mulla, Mosquito
News, £3.(3), 234-7(1963); Chem. Abs. 60, 2271f (1964).
(11) "Residues of Insecticides on Cover Crops Growing in Orchards After
Application of Organic Phosphorus Toxicants on the Trees", H. Maier-
Bode, Z. Pflanzenkrankh, Pflanzenschutz ^£(8), 449-59 (1963);
Chem. Abs. 60, 4690e (1964).
121
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1964
(12) "Nuclear Magnetic Resonance In the Examination of the Thermal
Decomposition of 0,0-Dimethyl 0-[4-(methylthio)-3-tolyl]Phos-
phorothioate", T. R. Fukuto, J. Agr. Food Chem. 12.(2), 169-71(1964);
Chem. Abs. 60, 13120g (1964).
(13) "Determination of Baytex in Biological Materials", A. Irudayasamy,
et al., Current Sci. (India)3^(3), 82(1964); Chem. Abs. 60, 13551a
(1964). —
(14) "Spectrophotometric Microdetermination of Lebycid", Y. Hirano, et
al., Anal. Chem. 3^.(4), 800-2(1964); Chem. Abs. 60, 16441b (1964).
(15) "The Use of Infrared Spectroscopy in the Analysis of Pesticide
Residues", N. T. Crosby, et al., Analyst £9_(1058), 319-27(1964);
Chem. Abs. 61, 4891b (1964).
(16) "Baytex", D. MacDougall, Anal. Methods Pesticides, Plant Growth
Regulators Food Additives, (Gunter Zweig. editor, Academic) 2
1-24(1964; Chem. Abs. 61, 11263g (1964).
(17) "The Determination of Traces of Phosphoric Esters by Oscillographic
Polarography", P. Nangniot, Anal. Chim. Acta 31(2), 166-74(1964);
Chem. Abs. 61, 12563c (1964).
(18) "Detection of Some Pesticides in Biological Material Using Thin-
Layer Chromatography", M. A. Klisenko, Khim. v Sel'sk. Khoz. 1964
(5), 21-3; Chem. Abs. 61, 12563e (1%4).
(19) "0,0-Dimethyl 0-(Methylthiophenyl)Phosphorothioates", Summitomo
Chemical Co., Ltd., Japan, 15,130 (1964), July 30; Chem. Abs. 61.
16016h (1964).
(20) "Detection of Insecticidal Phosphoric Acid Esters and Their Hydrolytic
Cleavage Products", H. W. Rahn, et al., Pharmazie 19(9), 597-602(1964);
Chem. Abs. 61, 16719f (1964).
(21) "Detection and Separation of the Most Important Organophosphorus
Pesticides by-Thin-Layer Chromatography", M. Salame, J. Chromato.
16.(3), 476-80(1964); Chem. Abs. 62, 11089e (1965).
(22) "Determination of MPP (0,0-Dimethyl 0-(4-Methylthio-m-tolyl)
Phosphorothioate) by Thin-Layer Chromatography", F. Tomita, et al.,
Noyaku Seisan Gijutsu 11, 13-16(1964); Chem. Abs. .63, 1174c (1965).
1965
(23) "Rapid Gas Chromatographic Analysis of Fractional Microgram Con-
centrations of Lebaycid, B. J. Gudzinovicz, Anal. Chem. 37(3),
439-40(1965); Chem. Abs. 62, 16900c (1965).
122
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(24) "The Detection of Thiophosphate Insecticides on Paper Chromatograms
with Congo Red", A. Irudayasamy, et al., Analyst JK) (1073), 503-4
(1965); Chem. Abs. 63, 15470h (1965).
(25) "Thin-Layer Chromatography of Agricultural Chemicals. II. Dry Thin-
Layer (Chromatographic Determination of 0,0-Dimethyl 0- p-Methyl-
4-(Methylthio)Phenyl]Phosphorothioate (MPP) in Formulations",
T. Kashiwa et al., Bunseki Kagaku JL4(9), 779-84(1965); Chem.
Abs. 63, 15525c (1965).
(26) "Screening Procedure for Organothiophosphate Pesticide Residues on
Fruits and Vegetables Using Microcoulometric Gas Chromatography",
R. C. Nelson, J. Assoc. Offic. Agr. Chemists ^8(4), 752-9(1965);
Chem. Abs. 63, 18932d (1965).
(27) "Identification and Quantitative Determination of Phosphorus
Insecticides in Biological Material. If!, R. Fischer, et al.,
Arch. Toxikol. 21(2), 101-20(1965); Chem. Abs. 64, 16554b (1966).
(28) "Colorimetric Determination of Baytex", M. Koibuchi, et al.,
Eisei Skikenjo Hokoku No. 83, 50-2(1965); Chem. Abs. £5, 20774d
(1966).
1966
(29) "Thin-Layer Chromatography of Pesticides", T. Salo, et al., Z.
Lebensm-Untersuch. - Forsch. 129(3), 149-53(1966); Chem. Abs.
64, 20546e (1966).
(30) "Ultraviolet Spectrophotometrie Method for Fenthion", F. B.
Ibrahim, et al., J. Agr. Food Chem. JL4_(4), 369-71(1966); Chem.
Abs. 65, 9650d (1966).
(31) "Screening Procedure for Organothiophosphate Pesticide Residues on
Fruits and Vegetables by Microcoulometric Gas Chromatography",
R. C. Nelson, J. Assoc. Offic. Anal. Chemists 49_(4), 763-6(1966);
Chem. Abs. j65, 17598a (1966).
(32) "Evaluation of Insecticides Against Two Species of Culex Mosquitos
on Okinawa", C. S. Lofgren, et al., Mosquito News .26(1), 52-9(1966);
Chem. Abs. 65, 6228b (1966).
(33) "Colorimetric Determination of Organophosphorous Insecticides with
Palladium Chloride", M. Fujimoto, et al.,Sankyo Renkyusho Nempo
18, 144-8(1966); Chem. Abs. 66, 114892k (1967).
(34) "Determination of Fenthion Residues in Plant and Animal Tissues by
Electron-Capture Gas Chromatography", R. J. Anderson, et al.,
J. Agr. Food Chem. 14(6), 619-22(1966); Chem. Abs. 66, 9997s (1967).
123
-------
(35) "Electrochemical Methods for Quantitative Analysis of Pesticide
Residues", P- Nangniot, Meded. Rijksfac. Landbouwwetensch., Gent
1966. 31(3), 447-73; Chem. Abs. 69_, 66438e (1968).
1967
(36) "Thin-Layer Chromatographic Separation Scheme for Insecticidally
Active Phosphoric Acid Esters", J. A. Guth, Pflanzenschutzberichte,
35(9-10), 129-43(1967); Chem. Abs. 67, 72784q (1967).
(37) "Direct Fluorescent Detection of Organothiophosphorus Pesticides
and Some of Their Sulfur-Containing Breakdown Products After
Thin-Layer Chromatography",M.T.H.\Ragab, J. Ass. Offic. Anal. Chem.
ti.sK.aj
. 67,
50(5), 1088-98(1967); Chem. Abs. 67, 9919p (1967).
(38) "Gas-Liquid Chromatographic Separation of Some Organophosphate
Pesticides, Their Hydrolysis Products, and Oxons," I. H. Suffetfit al,
Environ. Sci. Technol. 1(8), 639-43(1967); Chem. Abs. £7_, 107614p
(1967).
(39) "The Gas-Chromatographic Determination of Organophosphorus
Pesticides. II. A Comparative Study of Hydrolysis Rates",
J. H. Ruzicka, et al., J. Chromatogr. 31(1), 37-47(1967);cf. ibid 30,
92-9(1967); Chem. Abs. .68, 2191r (1968).
(40) "Effect of Phosphoric Esters on the Arthropods in the Apple Tree
Biozone in Relation to Their Density", F. Abdel-Salam, Z. Angew.
Zool. _54_(2), 233-83(1967); Chem. Abs. 68, 4856r (1968).
1968
(41) "The Chromatographic Determination of Organophosphorus Pesticides.
III. The Effect of Irradiation on the Parent Compounds", T. H.
Mitchell, et al.,J. Chromatogr.^2(1), 17-23 1968;Chem. Abs. 68,
67980s (19'68).
(42) "Nuclear Magnetic Resonance Studies of Phosphorus(V) Pesticides. I.
Chemical Shifts of Protons as a Means of Identification of
Pesticides", H. Babad,et al, Anal Chim Acts 41.C2), 259-68(1968); Chem.
Abs. 68, 77181w (1968)':
(43) "Determination of Fenthion and Five of its Metabolites in Corn,
Grass, and Milk", M. C. Bowman, et al.,J. Agr. Food Chem. 1968, 16(3),
399-402; Chem. Abs. 69, 1853s (1*968).
(44) "Determination of Organophosphorus Insecticides in Plant Material",
I. Pejkovic-Tadic, et al., Hrana Ishrana 1968, 9(1), 29-31;
Chem. Abs. 69, 58436n (1968).
(45) "High-Resolution N.M.R. Spectra of Pesticides. I. Organophosphorus
Pesticides", L. H. Keigh, et al., J. Ass. Offic. Anal. Chem. 1968.
51(5), 1063-94; Chem. Abs. 69, 75849s (1968).
124
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(46) "Thin-Layer Chromatography of Organophosphorus Insecticides with
Several Adsorbents and Ternary Solvent Systems", M. E. Getz,ret al.,
J. Ass. Offie. Anal. Chem. 1968, 51(5), 1101-7; Chem. Abs. 69,
75850k (1968).
(47) "Qualitative Analysis of Synthetic Organic Pesticides by Spot
Tests", M. Kanda et al., Nippon Holgaku Zasshi 1968, 22(3),
229-51; Chem. Abs. _72_, 65726x (1970).
1969
(48) "Pesticide Residues. Recovery of 65 Organophosphorus Pesticides
from Florisil with a New Solvent-Elution System", H. Beckman, .et al.,
J. Ass. Offic. Anal. Chem. 1969. 52(2), 286-93; Chem. Abs. .70,
86520z (1969).
(49) "Polyamide-Layer Chromatography of Organophosphorus Pesticides",
K. Nagasawa^et al.,J. Chromatogr., 1969, 39(3), 282-90; Chem.
Abs. .70, 114093h (1969).
(50) "Gas Chromatography of Organophosphorus Pesticides:Retention Times
and Response Data on Three Columns", R. Watts, et al., J. Ass.
Offic. Anal. Chem. 1969. 52(3), 513-21; Chem. Abs. 21» 12019s
(1969).
(51) "Reduction Mechanism of Organophosphorus Compounds", M. Y. Lee,
Daehan Hwahak Hwoejee 1969. 13(2), 141-7; Chem. Abs. _72_, 2815e
(1970).
(52) "Determination of 0,0-dimethyl 0-(3-methyl-4-Methylthiophenyl)
Thiophosphate and its Metabolites in Olives and Olive Oil",
I. Camoni, et al., Boll Lab. Chim. Prov. 1959, 20)3), 183-92;
Chem. Abs. ^2, 11420z (1970).
(53) "Rapid GLC [Gas-Liquid Chromatography] Method for Determining
Residues of Fenthion, Disulfoton, and Phorate in Corn, Milk,
Grass, and Feces", M. C. Bowman,K et al., J. Ass. Offic. Anal.
Chem. 1969. 52(6), 1231-7; Chem. Abs. _72, 41821z (H70.
(54) "Identification and Determination of Organophosphorus and
Carbamate Insecticides by Thin-Layer Chromatography", M.
Ramasamy, Analyst (London) 1969, 94(1125), 1075-80; Chem. Abs.
22, 77836w (1970).
(55) "An Analytical Study by Gas Liquid Chromatography and Radiochromato-
graphy of Tritium Labeled Lebaycid", M. DelMilagro Perez, Juanita
Enrg. Nucl. Rep. 1969; Chem. Abs. 73_» 2505m(1970).
(56) "Pesticide Residues. XIX. Determining Pesticide Residues in
Natural Waters, I. General Analytical Methods", R. Mestres, et al.,
Ann. Fals. Expert. Chim. 1969, 62(685), 75-85; Chem. Abs. 21»
34091c (1970).
125
-------
(57) "Baytex", V. G. Zharov, Tr. Tsent. Nauch.-Issled. Dezinfek. Inst.
1969, No. 20, 384-6; Chem. Abs. 75, 76311w (1971).
1970
(58) "GLC [Gas-Liquid Chromatographic] Retention Times of Pesticides and
Metabolites Containing Phosphorus and Sulfur on Four Thermally
Stable Columns", M. C. Bowman, et al., J. Ass. Offic. Anal. Chem.
1970, 53(3), 499-508; Chem. Abs. 73, 24179z (1970).
(59) "Effect of Ultraviolet Irradiation on the Thin-Layer Chromatography
of Insecticidal Phosphates and on Their Detection by the Benzo-
hydroxamic Acid Reaction", W, Ebing, J. Chromatogr. J970. 46(2),
180-6; Chem. Abs. 72^, 89161k (1970).
(60) "Chromatographic Determination of Trace Amounts of Pesticide
Residues", M. Beroza, et al., Trace Subst. Envoron. Health-3, Proc.
Univ. Mo. Annu. Conf., 3rd 1969 (Pub. 1970), 331-51; Chem. Abs.
74, 2963t (1971).
(61) "Method for Determination of Fenthion in Apples and Plums", J.
Zadrozinska, Rocz. Panstw. Zakl. Hig. 1970, 21(4), 345-53;
Chem. Abs. 74, 52202q (1971).
(62) "Identification and Determination of Fenthion (MPP) in Birds",
T. I. Kawahara, et al., Noyaku Rensasho Hokoku 1970, No. 10,
53-6; Chem. Abs. T±, 140007k (1971).
(63) "Enzymic Agar-Diffusion Method for Detecting Organophosphorus
Insecticide Residues in Products of Animal Origin", A. A.
Nepoklonov, et al., Tr. Vses. Nauch.-Issled. Inst. Vet. Sanit. 1970,
35, 383-90; Chem. Abs. 7£t 122722b (1972).
(64) "Gas-Chromatographic Determination of Pesticides. III. Determination
of Residues of Organophosphorus Pesticides", I. Takase, et al.,
Noyaku-Seisan Gijutsu 1979. 22, 13-21; Chem. Abs. 76, 23864t
(1972).
(65) "Synthesis of Baytex and its Insecticidal Properties", V. I. Vashkov,
et al., Tr. Tsent. Nauch.-Issled. Dezinfek. Inst. 1970, No. 19,
243-50; Chem. Abs. .78, 68121f (1973).
(66) "Gas-Chromatographic Determination of Pesticides. IV. Clean-up Method
for Organophosphorus Pesticide Residues in Rice Grain", I. Takase,
et al., Noyaku Seisan Gijutsu 1971, 23, 31-5; Chem. Abs. 76,
23867w (1972).
1971
(67) "Recovery of Organophosphorus Compounds Using the AOAC Multiresidue
Method:, J. R. Pardue, J. Ass. Offic. Anal. Chem. 1971. 54(2), 359-60;
Chem. Abs. 74, 110754J (1971).
(68) "Method for Confirmation of Organophosphorus Compounds at the Residue
Level", M. T. Shafik, et al., Bull. Environ. Contarn. Toxicol. 1971,
6(1), 17-19; Chem. Abs. 74, 124014e (1971).
126
-------
(69) "Simultaneous Gas Chromatographic Determination of Chlorinated
Hydrocarbons and Organophosphates in Plant Material", G. Becker,
Deut. Lebensm.-Rundsch, 1971. 67(4), 125-6; Chem. Abs. 75. 4459c
(1971).
(70) "Determination of Baytex Residues in the Tissues and Organs of
Animals by Thin-Layer Chromatography", V. V. Kadnikov, Khim.
Sel. Khoz, 1971. 9(4), 278-80; Chem. Abs. _75, 19110f (1971).
(71) "Sensitized Photodecomposition and Photosensitizer Activity of
Pesticide Chemicals Exposed to Sunlight on Silica Gel Chromatoplates",
G. W. Ivie, et al., J. Agr. Food Chem. 1971, 19(3), 405-9; Chem.
Abs. 75, 19168f (1971)
(72) "Routine Method for the Determination of Organophosphorus Insecticides
by Thin-Layer Chromatography", 0. Antoine, et al., J. fihromatogr.
1971. 58(2), 247-56; Chem. Abs. 75, 75234m (1971).
(73) "Thin-Layer Chromatography and Infrared and Ultraviolet Spectra of
Fenthion and Seven of its Degradation Products", I. H. Suffet,
et al., Water Res. 1971, 5(7), 473-90; Chem. Abs. 75, 109059a
(1971).
(74) "Biological Determination of the Active Principles of Some Insecticides",
M. P. Menezes, et al., Rev. Agr. (Sao Paulo) 1971. 46(1), 9-14;
Chem. Abs. 75, 117460q (1971).
(75) "Application of Indoxyl Acetate as Substrate for Enzymic Detection
of Organophosphorus Insecticides on Thin-Layer Chromatograms", M.
Bogusz, et al., Z. Rechtsmedizin 1971, 68(5), 267-72; Chem. Abs.
76 (1972).
(76) "Relation Between the Signal of an Electron-Capture Detector and the
Structure of Pesticides", D. B. Girenko, Tr. Vses, Soveshch.. Issled.
Ostatkov Pestits. Profil. Zagryazneniya Imi Prod. Pitan. Kormov Vnesh.
Sredy, 2nd 1971, 56-6; Chem. Abs. 78, 106828b (1973).
(77) "Determination of Lebaycid and Precursors by Gas Chromatography,
Infrared Spectroscopy, and Radiochromatography", M. J. Martin, et
al., Rev. Agroquim. Tecnol. Aliment. 1971, 11(3), 446-56; Chem.
Abs. 77, 71221y (1972).
(78) "Determination of Lebaycid in Animal Tissues", S. A. Serko, et al.,
Sb. Rab., Leningrad. Vet. Inst. 1971. N-. 32, 272-3; Chem. Abs.
7£, 16997x (1973)
127
-------
1972
(79) "The p-Value Approach to Quantitative Liquid-Liquid Extraction of
Pesticides from Water. I. Organophosphates. Choice of pH and
Solvent", I. H. Suffet, et al., J. Agr. Food Chem. 1972, 29(1), 52-6;
Chem. Abs. 76, 109005a '^1972).
(80) "Preparation of Lebaycid Labeled with Tritium at the Methyl Group",
M. M. Angoso, et al., An. Quim. 1972. 68(2), 159-65; Chem. Abs.
TT_, 34070c (1972).
(81) "Metallofluorescent Indicators as Spray Reagents for The In Situ
Determination of Organophosphorus Pesticides on Thin-Layer
Chromatograms", T. F. Bidleman, et al., Anal. Chim. Acta 1972,
60(1), 13-23; Chem. Abs. 77, 84271q (1972).
(82) "Chemical Hydrolysis of Some Organic Phosphorus and Carbamate
Pesticides in Aquatic Environments", S.D. Faust, et al.,
Environ. Lett. 1972, 3(3), 171-201; Chem. Abs. ^7, 110352p (1972).
(83) "Determination of Some Organothiophosphorus Pesticides with
Palladium Chloride Following Their Separation by Thin-Layer
Chromatography", D. A. Jovanovic, et al.,Acta Pharm. Jugoslav, 1972.
22(3), 91-6; Chem. Abs. ^78, 2806bx(1973).
(84) "Use of Thin-Layer Chromatography to Determine Selected Organo-
phosphorus Insecticides (Fenthion, Fenitrothion, and Malathion)
in Soil", K. Cywinska-Smoter, Rocz. Panstw. Zakl. Hig. 1972, 23(5),
505-12; Chem. Abs. _7jJ, 39090q (1973).
1973
(85) "Preparation and Infrared Spectra of Palladium Derivatives of
Some Organophosphorus Insecticides", T. F. Bidleman, et al.,
Talanta 1973, 20(1), 103-13; Chem. Abs. J7§, 120064f (1973).
(86) "Isotopic Dilution Determination of Lebaycid in Oranges", M. M.
Angoso, et al., J. Radioanal. Chem. 1973. 13(1), 149-54; Chem.
Abs. J78, 134537z (1973).
(87) "Detection of Organophosphorus Pesticides by In Situ Fluorometry
on Thin-Layer Chromatograom", G. L. Brun, et al., J. Chromatogr.
1973. 80(1), 117-23; Chem. Abs. 2i» 112253x (1973).
(88) "Electron-Donor-Acceptor Complexing Reagents in the Analysis of
Pesticides. VI. Influence of Structure in Detection and
Identification", J. D. MacNeil, et al., Mikrochim. Acta 1973.
(5), 641-50; Chem. Abs. 2i» 122492 (1973).
128
-------
FOLPET
1951
1. "PARASITICIDAL COMPOUNDS CONTAINING THE NSCCU GROUP", Standard Oil
Development Co., U.S. Patent 2,553,770, May 22, 1951; Chem. Abs. 45,
67911 (1951).
2. "PARASITICIDAL COMPOUNDS CONTAINING THE NSCC1- GROUP", Standard Oil
Development Co., U.S. Patent 2,553,771, May 22, 1951; Chem. Abs. 45,
6792c&g (1951).
3. "PARASITICIDAL COMPOUNDS CONTAINING THE NSCCK GROUP", Standard Oil
Development Co., U.S. Patent 2,553,776, May 22, 1951; Chem. Abs. 45.
6792c&g (1951).
1952
4. "A NEW CLASS OF ORGANIC FUNGICIDES", A.R. Kittleson, Science, 115,
84-6(1952); Chem. Abs. 46, 10134d (1952).
5. "N-(TRICHLOROMETHYLTHIO)IMIDES", Standard Oil Development Co.,
British Patent 666,636, Feb. 13, 1952; Chem. Abs. 46, 11232c (1952).
1953
6. "PREPARATION AND SOME PROPERTIES OF N-(TRICHLOROMETHYLTflIO)TETRA-
HYDROPHTHALIMIDE", A.R. KITTLESON, J. Agr. Food Chem. 1 677-9(1953);
Chem. Abs. 48, 5852g (1954).
1957
7. "CARCINOLYTIC ACTIVITY OF N-(TRICHLOROMETHYLTHIO)PHTHALIMIDE", K.
Aderhold, et al.; Naturwissenschaften 44,517-18(1957); Chem. Abs. 52,
4822e (1958).
1958
8. "ABSORPTIOMETRIC ANALYSIS OF N-(TRICHLOROMETHYLTHIO)-4-CYCLOHEXENE-l,
2-DICARBOXIMIDE(CAPTAN), H.P. Burchfield, et al., Contribs. Boyce
Thompson Inst. 19,411-16(1958); Chem. Abs. 53, 3577e (1959).
1959
9. "A NEW CLASS OF SULFENYL DERIVATIVES: PERHALOGENATED ALIPHATIC
SULFENYL FLUORIDES", Kober, J. Am. Chem. Soc. ul,4810-12(1959);
Chem. Abs. 54, 2152f (1960).
10. "N-(TRICHLOROMETHYLTHIO)IMIDES", Farbenfabriken Bayer Akt.-Ges.,
German Patent 972,502, July 30, 1959; Chem. Abs.. 55, 5429 (1961).
129
-------
I960
11. "ORGANIC FUNGICIDES I. (TRICHLOROMETHYLTHIO) DERIVATIVES", Barhera.
Quim. Ind. (Bilbao) 7(5), 183-9(1960); Chem. Abs. 63, 1173c (1965).
1961
12. "ORGANIC FUNGICIDES-SUBSTITUTES FOR COPPER-CONTAINING PREPARATIONS",
N.N. Mel'nikov, et al., Khim. Prom. 1969,692-4; Chem. Abs. 58, 471d,
(1963).
13. "RELATIVE TOXICITY OF PERCHLOROMETHYLMERCAPTAN DERIVATIVES TO MICE",
A.I. Solov'ev. Toksikol.i Farmakol. Yadokhim. Primenyaemykh Sel'sk.
Khpz., Hinskii Cos. Med. lost, i Nauchn.-Issled. Lab. Min. Zdravookhr.
Belorussk. SSR 1961, 75-8; Chem. Abs. 57, 88451 (1962).
1962
14. "THE FUNGITOXICITY OF CAPTAN". I. THE STRUCTURAL SPECIFICITY OF
CAPTAN AND SIX N-TRICHLOROMETHYLTHIO ANALOGS", D.V. Richmond, et al.,
Ann. Appl. Biol. 50, 33-43(1962); Chem. Abs. 57, 142251 (1962).
15. "INVESTIGATIONS IN THE USE OF THE MICROCOULOMETRIC GAS CHROMATOGRAPH
FOR PESTICIDE RESIDUE ANALYSIS", Jerry Burke and Loren Johnson (Food
& Drug Admin., Washington, D.C.). J. Assoc. Offic. Agr. Chemists 45,
348-54(1962); Chem. Abs. 57, 2626g (1962).
16. "THE PROMISING UTILITY OF INFRARED ASSAY OF PESTICIDES AND THEIR
RESIDUES. II", R. C. Blinn, et al., Res. Bull. 2(4), 3-11(1962);
Chem. Abs. 60, (1964).
17. "POLAROGRAPHIC DETERMINATION OF TRACE AMOUNTS OF FUNGICIDES OR
INSECTICIDES ON CULTIVATED PLANTS. IV. THE POLAROGRAPHIC DETERMINA-
TION OF H-TRICHLOROMETHYLTHIOTETRAHYDROPHTHALIMIDE (CAPTAN) AND
N-TRICHLOROMETHYLTHIOPHTHALIMIDE (PHALTAN)", P. Hangniot, et al.,
Bull. Inst. Agron. Stat. Rech. Gembloux 31(1), 110-26(1963); Chem.
Abs. 60, 12603a (1964).
1963
18. "FUNGICIDAL PHTHALD£LDES", California Research Corp., Belgium Patent
633,205, Dec. 1, 1963; Chem. Abs. 60, 15789c(1964).
19. "ALKALINE PURIFICATION OF TECHNICAL N-TRICHLOROMETHYLTHIOIMIDES",
J. Drabek, et al., Czech. Patent 107,115, Apr. 15, 1963; Chem. Abs.
60, 5403e (1964).
1964
20. "THE DEGRADATION OF CAPTAN, PHALTAN, AND DIPOLATAN BY LIGHT", G. Serra,
Phytiat. Phytopharn. 13(2), 107-10(1964); Chem. Abs. 62, 337h(1965).
130
-------
1964
21. "FLUORODICHLOROMETHYLTHIO DERIVATIVES AND THEIR USE IH PLANT PROTEC-
TION11, E. Kuehle, et al., Angew. Chem. 76(19), 807-16(1964); Chem.
Abs. 62, 3973b (1965).
22. "THIN-LAYER CHROMATOGRAPHY OF
-------
1967
33. "REACTIONS OP CAFTAN AND FOLPET WITH THIOL8", M.K. Li*, et •!.,
Experlentla 23(2), 81-2(1967); Chen. Abe. £6, 85034z (1967).
34. ''THE USE OF POLABOGRAPHY TO DETERMINE SMALL AMOUNTS OF FUNGICIDES
OR INSECTICIDES IM DEPOSITS OR RESIDUES OH PLANTS. VI. FOLAROCRAFHIC
DETERMINATION OF N-(l,l,2,2-TETRACHU>ROeTintLTH10 TETRAHYDROPHTHALIMIDE
OR OTHODIP0LATAN", R. Vervier, Ball. Rech. Agron. Genbloux 2(2), 369-76
(1967); Chen. Abe. 68, 58580J (1968).
35. "IMIDO PERHALOALKYL BISULFIDES", Chevron Research Co., U.S. Patent
3,356,572, Dec. 5, 1967; Che*. Ab». ££, 29441J (1968).
36. "REFINING M-POLYHALOALKYLTHIO)IMIDES OF DICARBOXYLIC ACIDS", Z. Stota,
et al., Czech. 122,756, April 15, 1967; Chen. Abe. ££, 29442k (1968).
1968
37 . "CAFTAN AMD STRUCTURALLY RELATED COMPOUNDS : THIN-LAYER AMD GAS-LIQUID
CHROMATOGRAPHY", I.H. Poaerantz, et al., J. A»». Offlc. Anal. Chen.,
1968, 51(5), 1058-62; Che*. Abe. 6£, 75856. (1968).
38 . "THE EXAMINATION OF MIXTURES OF CAPTAH AMD PHALTAN BY GAS CHROMATOGRAPHY",
A, Bevenue, et al., J. Chronatogr. 1968, 36(4), 529-31; Chen. Ab«. 69.
105285z (1968).
39. "TERATOGENIC POTENTIAL OF CAFTAN, FOLPET, AND DIPOLATAM", G. Kennedy,
et al., Toxicol. Appl. Fhamacol. 1968 13(3), 420-30; Chen. Ab«. ££,
105298f (1968).
40. "CHLORINE DETERMINATION IN PESTICIDES BY THE D I PHEWYL- SODIUM MTTHJD",
R. Llebnann, et al., Chen. Tech. (Berlin) 1968, 20(3), 169-70; Chen.
Ab0. 69, 2062v (1968).
41 . "GAS CHROMATOGRAPHIC DETERMINATION OF CHLORINATED PESTICIDE RESIDUES
IN VINES", M. Matta, Vini Ital. 1968, 10(54), 171-4; Chen. Ab*. 6£,
66468q (1968).
42. "DEGRADABILITY OF CAFTAN AND PHALTAN", A. Polizu, An. Inat. Cercet.
Prot. Plant., Acad. Stiinte Agr. 811 vice 1968 (Pub. 1970), 6, 495-9;
Chen Ab« . l*L> 19126r (1971) .
43. "FUNGICIDAL COMPOSITIONS", E. Merck, A.C. S. African Patent 67 07,305,
04 Sep. 1968; Chen. Ab». 2£, 767 64t (1969).
1969
44. "TESATOGENIC EFFECTS OF CAFTAN AMD RELATED COMPOUNDS IN THE DEVELOPING
CHICKEN EMBRYO", M. Verrett, et al., Ann. N.Y. Acad. Sci 1969, 160(1),
334-43; Chen. Aba. 21* B0134a (1969).
132
-------
45. "PESTICIDE RESIDUES. HX. DETERMINING PESTICIDE RESIDUES IB NATURAL
WATERS. I. GENERAL ANALYTICAL METHODS", R. Meatrea, Aon. Pal a.
Expert. Chim. 1969, 62(685), 75-85; Chen. Aba. ]£, 3409 Ic (1970)*
46. 'VJUANTITATTVE GAS-CHROMATOGRAPHIC DETERMINATION OF THE FUNGICIDE
RESIDUE OH GRAPES, IM MUST, AMD IB WINE AFTER APPLICATION OF ORTHO
PHALTAN. E. Lemper le, et al., Preaeniue' Z. Anal. Chen. 1969, 247(1),
49-52; Che*. Aba. 22, 11423c (1970). -
47. "AGRICULTURAL FUNGICIDES", E. Merck, A.-C., French Patent 1,559,693,
14 Mar 1969; Chen. Aba. j£, 2549* (1970).
1970
48. "EXTRACTION, CLEANUP, AND GAS-LIQUID CHROMATOGRAPHIC METHOD FOR THE
ANALYSIS OF CAFTAN, FOLPET, AND DIFOLATAN IN CROPS", I. Ponerautz,
J. Acs. Offic. Atul. Chen. 1970, 53(1), 154-7; Chen. Aba. 22, 77841u
(1970).
49. "GLC (GAS-LIQUID CHROMATOGRAPHIC) RETENTION TIMES OF PESTICIDES AND
METABOLITES CONTAINING PHOSPHORUS AND SULFUR ON FOUR THERMALLY STABLE
COLUMNS", M. C. Bowman, et «!., J. Aaa. Offlc. Anal. Chen. 1970,
53(3), 499-508; Chen. Abe. 22, 24179? (1970).
50. "THERMAL DECOMPOSITION OF FUNGICIDES OF THE PHTHALIMIDE TYPE", Flora
Pfelfer, et al., Proc. Anal. Chen. Conf., 3rd 1970, 2,371*7. Edited
by Buzaa, Ilona. Akad. Klado: Budapeat, Hung.; Chen. Aba. 7*- 52423n
(1971) .
51. "SYSTEMATIC IDENTIFICATION AND DETERMINATION OF PESTICIDES. 2. LOWER
LIMITS OF DETECTION OF PESTICIDES ON THIN LAYER PLATES", K. Suzuki,
et al., Noyaku Kenaaaho Hokoku 1970, No. 10, 24-31; Chen. Aba. 2£
4461* (1971).
52. "FUNGICIDAL AND ACARICIDAL M-(POLYHALOALKYLTHIO)PHTHALIMIDES", J.
Denecko, et al., Czech, Patent 135,056, 15 Jan 1970; Chen. Aba.
34493b (1971).
53. "FUNGICIDES", California Reaearch Corp., German Patent 1,542,706,
15 Jan 1970; Chen. Aba. 22 89250p (1970).
1971
54. "INFRARED AND ULTRAVIOLET SPECTRA OF SEVENTY-SIX PESTICIDES", R.C.
Core, et al., J. Aaa. Offic. Anal. Chen. 1971, 54(5), 1040-82; Chen.
, 117202g (1971).
55. "INVESTIGATION INTO THE TERATOGENIC POTENTIAL OF CAFTAN, FOLPET, AND
DIFOLATAN IN NONHUMAN PRIMATES", P. Vondruaka, et al., Toxicol. Appl.
Phamacol. 1971, 18(3), 619-24; Chen. Aba. ]£• 123980e (1971).
133
-------
56. "DETERMINATION OF THE TOTAL CHLORINE CONTENT OF PESTICIDES USING
A CHLORIDE-SELECTIVE MEMBRANE ELECTRODE", L. Vajda, et al., Hung.
Sci. Instrum. 1971, No. 20, 31-5; Chem. Abs. 77, 15357K (1972).
57- "INFRARED ANALYSIS OF PESTICIDE FORMULATIONS", S.W. Goza, J. Ass.
Off. Anal. Chem. 1972, 55(5), 913-17; Chem. Abs. 77, 160898s (1972).
58. "PREPARATION OF THE FUNGICIDES CAPTAN AND PHALTAN IN THE LABORATORY"
AND ON A SMALL INDUSTRIAL SCALE", G. Pfeifer, et al., Nehezvegyip. Kut
Intex. Kozlem, 1972, 4, 33-8; Chem. Abs. 2Z» 164369t (1972).
134
-------
MALATHION
1951
(1) "Chemical and Physical Properties of Organic Phosphorus Insecticides",
F. 1. Edwards, Jr., U. S. Dept. Agr. Bur. Entomol. and Plant Quarantine
E-832, 4 pp (1951); Chem. Abs. 46, 2742g (1952).
(2) "Adducts of Diesters of Dithiophosphoric Acid and Maleic and Fumaric
Esters", American Cyanamid Co., U. S. 2,578,652, Dec. 18, 1951; Chem.
Abs. 46, 6139c.
1952
(3) "Decreased Toxicity and Cholinesterase Inhibition in a New Series of
Dithiophosphates", G. A. Johnson et al., J. Econ. Entomol., 45, 279-83
(1952); Chem. Abs. ^7, 2123d (1953).
(4) "Synthesis of Some Mixed Esters of Dithiophosphoric Acid", N. N.
Mel'nikov et al., Doklady Akad. Nauk S.S.S.R. 86, 543-6 (1952); Chem.
Abs. 48, 556i (1954).
1953
(5) "The Isomerization of Organic Thionophosphate Insecticides", L.
Metcalf, J. Econ. Entomol. 46, 288-94 (1953); Chem. Abs. 48_, 4166d
(1954).
(6) "Organic Insectofungicides. XIV. Synthesis of Some Mixed Esters of
Dithiophosphoric Acid", N. N. Mel'nikov et al., Zhur. Obshchei Khim.,
23, 1352-7 (1953); Chem. Abs. 48, 9902d (1954).
1954
(7) "Colorimetric Estimation of Malathion Residues", M. V. Norris et al.,
J. Agr. Food Chem. 2, 570-3 (1954); Chem. Abs. 48, 14093d (1954).
(8) "Paper Chromatography of Some Organic Phosphate Insecticides. 111.
Effects of Light on Systox and Isosystox", J. W. Cook, J. Assoc.
Offic. Agr. Chemists 37, 984-7 (1954); Chem. Abs. 49, 2665b (1955).
1955
(9) "Polarographic Determination of S-(l,2-Dicarboethoxyethyl 0,0-dimethyl
Dithiophosphate (Malathion)", W. H. Jura, Anal. Chem. Abs. 49 525-8,
8745c (1955).
135
-------
1955
(10) "Preassay Purification of Tissue Extracts by Wax Column", W. R. Erwin
et al., J. Agr. Food Chem. 3, 676-9 (1955); Chem. Abs. 50, 523i (1956).
(11) "Paper Chromatography of Some Organic Phosphate Insecticides. IV.
Spot Test for In Vitro Cholinesterase Inhibitors", J. W. Cook, J.
Assoc. Offic. Agr. Chemists 38, 150-3 (1955); Chem. Abs. 49_, 16310c
(1955).
(12) "Preparing Phosphoric Acid Esters with Insecticidal Action", G.
Matolcsy et al. , Novenytermeles 4, 351-60 (1955); Chem. Abs. 51.
1521e (1957).
1956
(13) "Thermal Decomposition of Some Phosphorothioate Insecticides", J. B.
McPherson, Jr. et al., J. Agr. Food Chem. 4, 42-9 (1956); Chem. Abs.
.50, 4446d (1956).
(14) "Enzymic Methods for Insecticides. The Conversion of Some Thiono-
phosphates and a Dithiophosphate to In Vitro Cholinesterase Inhibitors",
U. 0. Fallscheer et al., J. Assoc. Offic. Agr. Chemists 39, 691-7
(1956); Chem. Abs. 50, 14168g (1956).
(15) "Polarographic and Amperometric Determination of Malathion", J. Prat
et al., Mem. Serv. Chim. etat (Paris) 41, 243-51 (1956-57); Chem. Abs.
_53, 8519b (1959).
(16) "Dialkylthiophosphorylmercaptosuccinic Acid and Derivatives: Prepara-
tion and Insecticidal Action", V. Bruckner, Novenytermeles, 5, 343-8
(1956); Chem. Abs. _52, 3665c (1958).
1957
(17) "Color Reaction of 2,6-Dibromo-N-Chloro-p-Benzoquinone Imine with
Thiophosphate Insecticides on Paper Chromatograms", J. J. Menn et al.,
J. Agr. Food Chem. _5, 601-2 (1957); Chem. Abs. 51, 16989h (1957).
(18) "Determination of Malathion", H. W. Conroy, J. Assoc. Offic. Agr.
Chemists 40, 230-5 (1957); Chem. Abs. 51, 6035f (1957).
(19) "Hydrolysis of the Phosphoric Acid Ester Insecticide", R. Muhlmann
et al., Z. Naturforsch. 12B, 196-208 (1957); Chem. Abs. 51, 99951
(1957).
(20) "Analysis of Pesticides by Paper Chromatography. I. Organic Phosphate
Insecticides", S. Nishiyama et al., Kagaku to Sosa 10, No. 3, 1-4
(1957); Chem. Abs. 52, 11344c (1958).
136
-------
(21) "Demonstration of Insecticide Residues in Plant Material (Vegetables
and Fruits) and the Separation of Individual Pesticides with the Help
of Paper Chromatography; R. Muller et al., Mitt. Gebiete Lebensm. u.
Hyg. 48, 152-97 (1957); Chen. Abe. 52, 1402Ig (1958).
1958
(22) "Determination of Malathion", H. W. Conroy, J. Assoc. Offie. Agr.
Chemists 41, 564-5 (1958); Chem. Abs. 53_, 602b (1959).
(23) "Chemical Studies on Insecticides. VI. The Rate of Hydrolysis of
Some Phosphorus Acid Esters", J. A. A. Ketelaar et al, Rev. trav.
chim. 77, 973-81 (1958); Chem. Abs. 53, 10920a (1959).
(24) "Chromatography of Organic Insecticides. I. Separation of Insecti-
cides on Phenylcellosolve-treated Paper", T. Shishido et al., Nippon
Nogei-kagaku Kaishi 32, 956-60 (1958); Chem. Abs. 53, 15455f (1959).
(25) "Adaptability and Sensitivity of Fluorescence Method for Developing
Spots by Organic Phosphate Insecticides on Paper Chromatograms", Yu.
N. Fadeev et al., Org. Insektofugitsidy i Gerbitsidy, 1958, 144-6;
Chem. Abs. 54, 15809c (1960).
(26) "Deodorization of 0,0-Dimethyl Dithiophosphate of Diethyl Mercapto-
succinate", J. N. Escobar, U. S. 2,844,619, July 22, 1958; Chem. Abs.
,53, 1626e (1959).
(27) "Dithiophosphate Esters", American Cyanamid Co. Brit. 794,597, May 7,
1958; Chem. Abs. 53, 1144a (1959).
1959
(28) "Gas Chromatography of Pesticides", C. M. Coulson et al., J. Agr. Food
Chem. 7, 250-1 (1959); Chem. Abs. 53, 19280d (1959).
(29) "Note on the Conversion of Some Organophosphate Pesticides to Less
Polar Compounds by Ultraviolet Light", J. W. Cook et al., J. Assoc.
Offic. Agr. Chemists 41, 211-12 (1959); Chem. Abs. 53, 9556b (1959).
(30) "Determination of Malathion", H. W. Conroy, J. Assoc. Offic. Agr.
Chemists 52, 551 (1959); Chem. Abs. 53, 19189g (1959).
(31) "Bioassays of Weathered Residues of Several Organophosphorus
Insecticides", B. G. Hightower, J. ECon. Entomol. 52, 840-2 (1959);
Chem. Abs. 55, 20306f (1961).
(32) "Detection of Thiophosphoric Esters", R. Fischer et al., Sci. Pharm.
27, 1-6 (1959); Chem. Abs. 53, 16830a (1959).
(33) "Microdetermination of Parathion (and Related Compounds)", Yu-Shih
Chen, Bull. Assoc. Agr. Chem. Natl. Taiwan Univ. (Formosa) 8, 21-4
(1959); Chem. Abs. 53, 22707i (1959).
137
-------
(34) "Preparation of Malathion-Type Compounds", G. Bruckner, Nehezvegyipari
Kutato Intezet Kozlemenyei 1, 313-16 (1959); Chem. Abs. 54. 113641
(1960).
(35) "Qualitative Analyses of Organic Phosphorus Color Reactions and
Simple Detection", K. Sera et al., Kumamoto Med. J. 12, 193-213 (1959);
Chem. Abs. 54, 11813d (1960).
(36) "Qualitative Analysis of 17 Organophosphorus Compounds by Paper
Chromatography", A. Hatsunaga, Ibid. 214-19; Chem. Abs. 54, 11813e
(1960).
(37) "Determination of Organophosphoric Poisons. Determination of Malathion
in Food and Water", M. Stevanovic et al., Vojnosanit. Pregled 16,
307-9 (1959); Chem. Abs. 54 25347e (1960).
(38) "Stabilization and Deodorization of Phosphate Pesticides", American
Cyanamid Co., U. S. 2,879,284, Mar. 24, 1959; Chem. Abs. 53_, 12576a
(1959).
1960
(39) "Microcoulometric Gas Chromatography of Pesticides", D. M. Coulson
et al., J. Agr. Food Chem. 8, 399-402 (1960); Chem. Abs. 55, 17997f
(1961).
(40) "Automated Enzymic Assay of Organic Phosphate Pesticide Residues",
G. D. Winter, Ann. N.Y. Acad. Sci. 87, 875-82 (1960); Chem. Abs. 55,
17997g (1961).
(41) "Methods for Determining Malathion", D. Upham, J. Assoc. Offie. Agr.
Chemists 43, 360-4 (1960); Chem. Abs. 54, 21621f (1960).
(42) "Separation and Identification of Eleven Organophosphate Pesticides
by Paper Chromatography: Delnav, Diazinon, EPN, Guthion, Malathion,
Methylparathion, Parathion, Phosdrin, Ronnel, Systox, and Trithion",
L. C. Mitchell, J. Assoc. Offic. Agr. Chemists 43, 810-24 (1960);
Chem. Abs. 55, 5845e (1961).
(43) "Spot Test Detection of Esters of Noncarboxylic Acids", F. Feigl
et al., Chemist-Analyst 49, 13-14 (1960); Chem. Abs. 55, 18453b
(1960).
(44) "Detection of Plant Pesticides in Mixtures by Infrared Spectroscopy",
W. Fischer et al., Z. anal. Chem. 172, 175-92 (1960); Chem. Abs.
54, 13525i (1960).
(45) "Behavior Toward H-jAsO^ of 0,0-Dialkyldithiophosphorylacetic Acids
and Their Derivatives, and a Selective Analysis of These Compounds",
R. Fusco et al., Chlm. e ind. (Milan) 42, 337-47 (1960); Chem. Abs.
55, 21985f (1961).
138
-------
(46) "Aging Tests on Emulsiftable Concentrates of Organo Phosphorus
Insecticides", K. Okada et al., Noyaku Seisan Gijutsu No. 3, 33-6
(1960); Chem. Abs. 55_, 14803c (1961).
(47) "Purification of an Organophosphoric Acid Ester", Sumitomo Chemical
Co., Ltd. U. S. 2,962,521, Nov. 29, I960; Chem. Abs. 55_, 13313g
(1961).
(48) "Refining of Organic Phosphates", Sumitomo Chemical Industry Co.,
Ltd., Japan, 17,483 ('60), Nov. 29; Chem. Abs. 55, 16422d (1961).
1961
(49) "The Determination of Organophosphorus Insecticides in Vegetables:
A General Method for Insecticide Residues", E. Q. Laws et al.,
Analyst 86, 249-55 (1961); Chem. Abs. 55, 20257f (1961).
(50) "Screening Method for Pesticide Residues on Fruits and Vegetables",
A. Major, Jr. et al., J. Assoc. Offic. Agr. Chemists 44, 202-7 (1961);
Chem. Abs. 55, 16841e (1961).
(51) "Determination of Malathion in Formulations", J. H. Ware, J. Assoc.
Offic. Agr. Chemists 44, 608-10 (1961); Chem. Abs. 55, 23907f (1961).
(52) "The Effect of Ultraviolet Light (2537 A) on 141 Pesticide Chemicals
by Paper Chromatography", L. C. Mitchell, J. Assoc. Offic. Agr.
Chemists 44, 643-712 (1961); Chem. Abs. 56, 3849e (1962).
(53) "lexicological Detection and Determination of Thiophosphoric Acid
Esters. II", R. Fischer et al., Pflanzenschutz Ber. 27, 165-76 (1961);
Chem. Abs. 59, 5677e (1963).
(54) "Synthesis of Malathion (0,0-Dimethyl S-bis(1,2-Diethoxycarbony1)ethyl
Phosphorodithioate)", Ch'un-Sheng Wu et al., Rept. Taiwan Sugar Expt.
Sta. No. 24, 119-42 (1961); Chem. Abs. 56, 4602c "(1962).
(55) "Preparation of Carbophos Compound", N. N. Mel'nikov et al., Tr.
Nauchn. Inst. po Udobr i Insektofung, No. 171, 7-14 (1961); Chem.
Abs. 57., 12298g (1962).
(56) "The Determination of Malathion Residues", S. D. Rossouw, S. African
J. Agr. Sci. 4, 435-7 (1961); Chem. Abs. 56, 9164c (1962).
(57) "Thin-Layer Chromatographic Detection of Insecticides", J. Bacumler
et al., Helv. Chim. Acta. 44, 1162-4 (1961); Chem. Abs. 56, 12036a
(1961).
(58) "Reducing Objectionable Odor of Insecticidal Phosphorodithioate
Compounds", American Cyanamid Co., U. S. 2,980,723, Apr. 18, 1961;
Chem. Abs. 55, 21467f (1961).
139
-------
1962
(59) "Use of Stabilizing Agents to Decrease Decomposition of Malathion
on High-Sorptive Carriers", J. A. Polon et al., J. Agr. Food Chem.
10, 244-8 (1962); Chem. Abs. 57, 8962b (1962).
(60) "Electrochemical Determination of Organophosphorus Compounds", 6. 6.
Guilbault et al., Anal. Chem. 34, 1437-9 (1962); Chem. Abs. 58, 888g
(1963).
(61) "Polarographic Microdetermination of Parathion and Malathion in
Admixture", D. E. Ott et al., Analyst 87, 70-2 (1962); Chem. Abs.
_57_, 8960e (1962).
(62) "Method for Determining Malathion", J. H. Ware, J. Assoc. Offie. Agr.
Chemists 45, 529-30 (1962); Chem. Abs. 57_, 15557g (1962).
(63) "Photometric Microdetermination of Malathion", B. J. Kallman, Chemist-
Analyst 51, 75-6 (1962); Chem. Abs. .57, 17130g (1962).
(64) "Electron Capture With an Argon lonization Detector in Gas Chromato-
graphic Analysis of Insecticides", A. D. Moore, J. Econ. Entomol. 55,
271-2 (1962); Chem. Abs. 7675a (1962).
(65) "The Promising Utility of Infrared Assay of Pesticides and Their
Residues. 11", R. C. Blinn et al., Pesticide Res. Bull. 2(4), 3-11
(1962); Chem. Abs. £0, 13811g (1964).
(66) "Detection of Malathion in Foods", J. A. McFarlane, J. Sci. Food Agr.
13, 308 (1962); Chem. Abs. 57_, 11608a (1962).
(67) "Nuclear Magnetic Resonance (N.M.R.) Studies of Organophosphorus
Compounds. 111. MeOP and MeSP Groups", G. Mavel et al., J. Chim.
Phys. 59, 762-71 (1962); Chem. Abs. 58, 2342c (1963).
(68) "Thin-Film Chromatography in the Analysis of Insecticide Residues",
T. Salo et al., Z. Lebensm.-Untersuch.-Forsch. 117, 369-71 (1962);
Chem. Abs. 57., 12957e (1962).
(69) "Chemistry of Stability of Pesticides. III. The Deterioration of
Formulated Malathion and EPN by Ultraviolet Irradiation", K. Okada
et al., Nippon Nogeikagaku Kaishi 36(2), 240-4 (1962); Chem. Abs. 61,
4891e (1964).
1963
(70) "Gas Chromatographic Determination of Organophosphorus Insecticides
Using the Zeisel Alkoxyl Reaction", W. H. Gutenmann et al., J. Agr.
Food Chem. 11(6), 470-1 (1963); Chem. Abs. 59, 15873g (1963).
(71) "Thin-Layer Chromatography for Insecticide Analysis", K. C. Walker
et al., J. Assoc. Offic. Agr. Chemists 46, 250-61 (1963); Chem. Abs.
58, 14626g (1963).
140
-------
(72) "Changes in Official Methods Analysis Made at the Seventy-Seventh
Annual Meeting", October 14, 15, 16, and 17, 1963., Anon., J. Assoc.
Offic. Agr. Chemists 47(1), 170-202 (1964); Chem. Abs. 60, 13537h
(1964).
(73) "Applications of the Microcoulometric Titrating System as a Detector
in Gas Chromatography of Pesticide Residues", J. A. Challacombe et al.,
Residue Rev. 5, 57-72 (1963); Chem. Abs. 61, 9975h (1964).
(74) "Analysis of Organophosphorus, Organochlorine Insecticide Residues
in Food by Gas Chromatography", T. Nishlmoto et al., Shokuhin Eiseigaku
Zasshi 4, 192-7 (1963); Chem. Abs. 60, 4690a (1964).
1964
(75) "Gas Chromatography Retention Times and Sensitivity Data for Insecti-
cides and Herbicides", E. J. Bonelli, J. Agr. Food Chem. 12(4), 333-6
(1964); Chem. Abs. 61, 7635f (1964).
(76) "Cryoscopic Analysis of Organic Phosphate Pesticides; Malathion,
Dimethoate, 0,0-Diethyl 0-(2-Pyrazinyl)phoBphorothioate, and Phorate",
R. J. Best et al., J. Agr. Food Chem. 12(6), 546-9 (1964); Chem. Abs.
62, lOOld (1965).
(77) "The Detection of Organophosphorus Pesticides on Thin-Layer Chromato-
grams", P. J. Bunyan, Analyst 89 (1062), 615-18 (1964); Chem. Abs. 61,
15282f (1964).
(78) "Malathion", G. L. Sutherland, Anal. Methods Pesticides, Plant Growth
Regulators and Food Additives (G. Zveig, editor), Academic, j2, 283-93
(1964); Chem. Abs. 61, (1964).
(79) "Determination of Malathion in Formulations", E. J. Orloski, J. Assoc.
Offic. Agr. Chemists 47(2), 248-52 (1964); Chem. Abs. 60, 15078g (1964)
(80) "Chromatographic Separation of Malathion Prior to Infrared Spectro-
photometric Estimation", R. C. Double, J. Assoc. Offic. Agr. Chemists
47(4), 693-5 (1964); Chem. Abs. *&_, 9977c (1964).
(81) "Thin-Layer Chromatography for Organothiophosphate Pesticide Residue
Determination", M. F. Koracs, Jr., J. Assoc. Offic. Agr. Chemists 47
(6), 1097-102 (1964); Chem. Abs. 62, 4517h (1965).
(82) "Thin-Layer Chromatography of Organophosphorus Pesticides and Acids
on Microchromatoplates", C. W. Stanley, J. Chromatog. 16(3), 467-75
(1964); Chem. Abs. 62, 11090a (1965).
(83) "Detection and Separation of the Most Important Organophosphorus
Pesticides by Thin-Layer Chromatography", M. Salame, J. Chromatog.
16(e), 476-80 (1964); Chem. Abs. 62, 11090b (1965).
141
-------
(84) "Manufacture of Malathion", R. R. Fatel et al., Pestle. Symp., 69-72,
(1964); Chem. Abs. 72_, 2516h (1970).
(85) "Detection and Identification of the Residues of the Organophosphorus
Pesticides by Gel Electrophoresis", P. Bruaux et al., Ann. Biol. Clin.
(Paris) 22(3-4), 375-98 (1964); Chem. Abs. 61, 6303a (1964).
(86) "The Determination of Traces of Phosphoric Esters by Oscillographic
Polarography", P. Nanguiot, Anal. Chlm. Acta 31(2), 166-74 (1964);
Chem. Abs. 61, 12563c (1964).
(87) "Detection of Some Pesticides in Biological Material Using Thin-Layer
Chromatography", M. A. Klisenko, Khim. v Sel'sk. Khoz. 21-3(5) (1964);
Chem. Abs. 61, 12563d (1964).
(88) "Photoelectric Colorimetric Studies of the Stability of Malathion in
Dust Concentrate", Chung-Sung Woo, Taiwan Tang Yeh Shih Yen So Yen
Chiu Hui Pao No. 34, 119-34 (1964); Chem. Abs. 62., 9719h (1965).
(89) "Pesticide Residues. Use of an Aerograph Flame lonization Detector
as a Thermionic Detector. Application to Organophosphate Insecticide
Research", R. Mestres, et al., Trav. Soc. Pharm. Montpellier 24(4),
283-303 (1964); Chem. Abs. 63, 13970d (1965).
(90) "Determination of Some Organophosphorus Insecticides by Gas Liquid
Partition Chromatography", M. Horiguchi et al., Chem. Pharm. Bull.
(Tokyo) 12(11), 1315-19 (1964); Chem. Abs. £2, 5823g (1965).
(91) ."Detection and Determination of Parathion by Gas Chromatography with
an Electron-Capture Detector", F. Lodl, Farmaco (Pavia), Ed. Prat.
19(11), 560-6 (1964); Chem. Abs. 62, 5824b (1965).
(92) "Determination of the Content and Stability of Malathion", L. Lipparini,
Rass. Chlm. 16, 180-2 (1964); Chem. Abs. 66_, 85054f (1967).
(93) "Evaluation of Minute Amounts of Some Phospho-Organic Compounds in
Plant Material by Means of Paper Chromatography", J. Zadrozinska,
Roczniki Panstvowego Zakladu Hig. 15(1), 5-12 (1964); Chem. Abs. 61,
6262a (1964).
(94) "Stabilization of Malathion", Toa Agricultural Chemical Co., Ltd.
and Takemoto Yushi Co., Ltd., Japan 500 (*64), Jan. 22; Chem. Abs.
60, 13816c (1964).
(95) "Dithiophosphates", Dainlppon Ink & Chemicals, Inc., Japan, 21,514
('64), Oct. 1; Chem. Abs. 62, 10338c (1965).
(96) "S-(l,2-Carboethoxylethyl) 0,0-Dlmethyl Dlthiophosphate", Dainlppon
Ink & Chemicals, Inc., 21,831 (*64), Oct. 5; Chem. Abs. .62, 11688f
(1965).
142
-------
1965
(97) "Simultaneous and Selective Detection of Phosphorus, Sulfur, and
Halogen in Pesticides by Microcoulometric Gas Chromatography", H. P.
Burchfield et al., J. Agr. Food Chem. 13(6), 511-16 (1965); Chem.
Abs. 64, 4193b (1966).
(98) "The Detection of Thiophosphate Insecticides on Paper Chromatograms
with Congo Red", A. Irudayasamy et al., Analyst 90 (1073), 503-4
(1965); Chem. Abs. 63, 15470g (1965).
(99) "Determination of Organophosphorus Insecticide Residues Using the
Emission Spectrometric Detector", C. A. Bache et al., Anal. Chem.
37(12), 1477-80 (1965); Chem. Abs. 64, 1288a (1966).
(100) "An Approach to the Separation, Identification, and Determination
of at Least Ten Organophosphate Pesticide Residues in Raw Agricultural
Products", D. F. McCaulley, J. Assoc. Offic. Agr. Chemists, 48(3),
659-65 (1965); Chem. Abs. 63, 7564h (1965).
(101) "Screening Procedure for Organothiophosphate Pesticide Residues on
Fruits and Vegetables Using Microcoulometric Gas Chromatography",
R. C. Nelson, J. Assoc. Offic. Agr. Chemists 48(4), 752-9 (1965);
Chem. Abs. 63, 18932d (1965).
(102) "A Sweep Codisfiliation Cleanup Method for Organophosphate Pesticides.
1. Recoveries From Fortified Crops", R. W. Storherr et al., J. Assoc.
Offic. Agr. Chemists 48(6), 1154-8 (1965); Chem. Abs. 64_, 8847d (1966).
(103) "The Detection of Pesticides by Means of Infrared Emission Spectroscopy",
I. Coleman, Develop. Appl. Spectrosc. 5, 193-201 (1965); Chem. Abs.
J56, 64624b (1967).
(104) "Selective Detection of Phosphorus, Sulfur, and Halogen Compounds in
the Gas Chromatography of Drugs and Pesticides", H. P. Burchfield
et al., J. Gas Chromatog. 3(1), 28-34 (1965); Chem. Abs. 6£, 11629e
(1965).
(105) "Electrolytic Conductivity Detector for Gas Chromatography", D. M.
Coulson, J. Gas Chromatog. 3(4), 134-7 (1965); Chem. Abs. 63, 6238f
(1965).
(106) "Simplified Gas-Chromatographic Analysis of Pesticides from Blood",
P. L. Kirk, Proc. Can. Soc. Forensic Sci. 4, 155-65 (1965); Chem.
Abs. 63, 12251c (1965).
(107) "Simplified Gas Chromatographic Analysis of Pesticides from Blood",
N. C. Jain et al., J. Pharm. Pharmacol. 17(6), 362-7 (1965); Chem.
Abs. 63, 6257d (1965).
143
-------
(108) "Gas-Liquid Chromatography of Organophosphorus Pesticides", J.
Kanazawa et al., Agr. Biol. Chem. (Tokyo) 29(1), 56-60 (1965);
Chem. Abs. 62, 12385a (1965).
(109) "Spectrophotometric Determination of Malathion with Bismuth Nitrate",
M. Yamauchi, Botyu Kagaku 30(1). 18-24 (1965); Chem. Abs. 63, 14045h
(1965). ~~
(110) "Analysis of Allethrin by Gas Chromatography", S. Kawai et al., Eisei
Shikenjo Hokoku No. 83, 41-2 (1965); Chem. Abs. 66, 1824y (1967).
(Ill) "Separation of Mixtures and Detection of Trace Amounts of Some Organo-
phosphorus Pesticides in Plant Material by Means of Paper Chromatography",
J. Zadrozinska, Roczniki Pantswowego Zakladu Hig. 16(1), 53-63 (1965);
Chem. Abs. £2, 16876g (1965).
(112) "Determination of Selected Phosphoorganic Pesticides (Parathion,
Methylparathion, Diazinon, Malathion Gusathion, Meta-Systox, and
Dipterex) by Thin-Layer Chromatography Method", J. Zadrozinska,
Roczniki Pantswowego Zakladu Hig. 16(4), 397-405 (1965); Chem. Abs.
64, 2684h (1966).
(113) "lexicological Analysis of Organic Phosphorus Insecticides", A. Silva
Santos, Rev. Port. Farm. 15(3), 367-74 (1965); Chem. Abs. 64, 11794d
(1966).
(114) "New Colorimetric Determination of Malathion and Its Technical Applica-
tions", G. A. Mora., Inform. Quim. Anal. (Madrid) 19(2), 63-9 (1965);
Chem. Abs. 63, 8981c (1965).
(115) "Detection of Pesticides by a Combination of Two-Channel Gas Chroma-
tography and Spectrophotometry", H. Brandenberger et al., Mitt.
Gebiete Lebensm. Hyg. 56(4), 281-92 (1965); Chem. Abs. 64, 18340c
(1966).
(116) "Determination of Malathion and of the Intermediate Products of Its
Synthesis in the Air", M. A. Klisenko et al., Gigiena Truda i Prof.
Zabolevaniya 9(1), 54-6 (1965); Chem. Abs. 62, 16871h (1965).
1966
(117) "Estimation of Malathion by Oxidation With Chloramine-T", V.
Lakshminarayana, J. Agr. Food Chem. 14(1), 55-6 (1966); Chem. Abs.
64, 11791c (1966).
(118) "Low Pressure Emission Spectrometric Determination of Parts per
Billion Residue Levels of Phosphorus Insecticides", C. Bache, Ana.
Chem. 38(12), 1757-8 (1966); Chem. Abs. £6, 1817j (1967).
(119) "Semiquantitative Determination of Organophosphorus Insecticides by
the Ring-Oven Technique with Preliminary Thin-Layer Chromatography11,
I. M. B. Celap et al., Analyst 91(1086), 595-7 (1966); Chem. Abs.
65, 20772h (1966).
144
-------
(120) "An Improved Screening Method for Chlorinated and Thiophosphate
Organic Insecticides in Foods and Feeds", B. L. Samuel, J. Assoc.
Offie. Anal. Chemists 49(2), 346-53 (1966); Chem. Abs. 65, 2894b
(1966).
(121) Gas Chromatographic Column for Pesticide Residue Analysis; Retention
Times and Response Data", J. A. Burke et al., J. Assoc. Offie. Anal.
Chemists 49(2), 374-85 (1966); Chem. Abs. 65, 2894g (1966).
(122) "Screening Procedure for Organothiophosphate Pesticide Residues on
Fruits and Vegetables by Microcoulometric Gas Chromatography", R. C.
Nelson, J. Assoc. Offic. Anal. Chemists 49(4), 763-6 (1966); Chem.
Abs. 65, 17598a (1966).
(123) "Mass Spectra of Some Organophosphorus Pesticide Compounds", J. N.
Damico, J. Assoc. Offic. Anal. Chemists 49(5), 1027-45 (1966); Chem.
Abs. 66, 1834k (1967).
(124) "Sodium Flame Detector of Increased Stability for Phosphorus-Containing
Pesticides", D. R. Coahran, Bull. Environ. Contain. Toxicol. 1(4), 141-8
(1966); Chem. Abs. 65, 17623d (1966).
(125) "Phosphorus Detector for Pesticides Analysis", C. H. Hartmann, Bull.
Environ. Contain. Toxicol. 1(4), 159-68 (1966); Chem. Abs. 65, 17623e
(1966).
(126) "Flame Photometric Detector. Application of a Specific Detector for
Phosphorus and for Sulfur Compounds Sensitive to Subnanogram Quantities",
S. S. Brody et al., J. Gas Chromatog. 4(2), 42-6 (1966); Chem. Abs.
64, 13378b (1966).
(127) "Modified Hydrogen Flame-Ionization Detector, Highly Sensitive and
Selective for Phosphates", R. V. Hoffman, Lect. Gas. Chromatogr.,
137-47 (1966); Chem. Abs. _70, 95709v (1969).
(128) "Screening Tissues and Urine for Pesticides", M. M. Luckens, J.
Forensic Sci. 11(1), 64-73 (1966); Chem. Abs. 64, 20550c (1966).
(129) "Determination of Organophosphorus Insecticide Residues Using
Cooke's Emission Spectroscopic Detector", C. A. Bache et al.,
Residue Rev. 12, 35-44 (1966); Chem. Abs. 65_, 7895e (1966).
(130) "Infrared Emission Spectra of Quantities of Pesticides in the Micro-
gram Range", I. Coleman et al., Spectrochim. Acta 22(7), 1293-8 (1966);
Chem. Abs. 65, 6229f (1966).
(131) "Thin-Layer Chroma tography of Pesticides", T. Salo et al., Z. Lebensm.-
Untersuch. -Forsch. 129(3), 149-53 (1966); Chem. Abs. 64_, 20546d
(1966).
145
-------
(132) "The Infrared Spectroscopic Detection of Plant Protective Agents
from Organic Material", G. Doerlng et al., Deut. Z. Gee. Gerichtl.
Med. 57(1-2); 341-52 (1966); Chem. Abs. 65, 7932e (1966).
(133) "Methods for Market Control of Organophosphate Residues in Fruit and
Vegetables", Krause, Chr., Z. Pflanzenkr. Pflanzenschutz, 73(6), 335-
45(1966); Chem. Abs. 7£, 18968b (1969).
(134) "Determination of Malathion Residues on and in Vegetables and Fruits",
M. Yamauchi, Bochu Kagaku 31(3), 113-20 (1966); Chem. Abs. 68, 48338x
(1968).
(135) "Residue Analysis of Agricultural Chemicals. III. Electron-capture
Gas Chromatography of Various Pesticides", J. Kanazawa et al., Nippon
Nogei Kagaku Kaishi 40(4), 178-84 (1966); Chem. Abs. £5, 4571f (1966).
(136) "Gas Chromatographic Analysis of Pesticides. II. Gas Chromatographic
Determination of Organophosphorus Pesticides", H. Takehara et al.,
Nippon Nogei Kagaku Kaishi 40(11), 394-400 (1966); Chem. Abs. 6>6,
94159w (1967).
(137) "Colorimetric Determination of Organophosphorous Insecticides with
Palladium Chloride", M. Fujimoto et al., Sankyo Kenkyusho Nempo 18,
144-8 (1966); Chem. Abs. 616, 114892k (1967).
(138) "Analysis of Phytotherapeutic Products. IX. Malathion11, A. R.
Castro et al., Bol. Patol. Veg. Entomol. Agr. 29, 413-33 (1966);
Chem. Abs. £8, 28693f (1968).
(139) "Bioelectric Method for the Detection of [Pesticidal] Anticholines-
terases", P. L. Cannon, Jr. et al., U. S. 3,275,534, Sept. 27, 1966;
Chem. Abs. £6, 1875r (1967).
(140) "Thiophosphoric Esters", Verdugt's Industrie Hand elsonderneming N. V.
Neth. Appl. 6,410,295, March 4, 1966; Chem. Abs. 65_, 2126d (1966).
(141) "0,0-Dimethyl-S-(l,2-Dicarboethoxyethyl) Dithiophosphate", Instytut
Przemyslu Organicznego, Pol. 50,671, March 19, 1966; Chem. Abs. 66,
65123z (1967).
1967
(142) "Detector Cell for Measuring Picogram Quantities of Organophosphorus
Insecticides, Pyrethrin Synergists, and Other Compounds by Gas
Chromatography", W. N. Bruce, J. Agr. Food Chem. 15(1), 178-81
(1967); Chem. Abs. 66, 54499a (1967).
(143) "The Determination of Malathion in Formulations by a Method Based
on Cleavage by Alkali", A. C. Hill et al., Analyst (London) 92(1097),
496-500 (1967); Chem. Abs. 67_, 116093v (1967).
146
-------
(144) "Colorimetrlc Analysis of Malathion and Parathion Using Fluoborlc
Acid", D. E. Long, Anal. Lett. 1(2), 61-5 (1967); Ghent. Abs. 68_,
38473y (1968).
(145) "Direct Fluorescent Detection of Organothiophosphorus Pesticides
and Some of Their Sulfur-Containing Breakdown Products After Thin-
Layer Chromatography", M. T. H. Ragab, J. Ass. Offie. Anal. Chem.
50(5), 1088-98 (1967); Chem. Abs. 67, 99119p (1967).
(146) "A Rapid Micromethod of Sample Cleanup for Gas Chromatographic
Analysis of Insecticidal Residues in Plant, Animal, Soil, and Surface
and Ground Water Extracts", A. M. Kadoum, Bull. Environ. Contam.
Toxicol. 2(5), 264-73 (1967); Chem. Abs. 67, 99128r (1967).
(147) "Improved Gas Chromatographic Systems for Determining Organochlorine
Pesticide Residues in Wildlife", J. H. Simmons et al., J. Chromatogr.
27(1), 253-5 (1967); Chem. Abs. 67_, 10437v (1967).
(148) "The Gas-Chromatographlc Examination of Organophosphorus Pesticides
and Their Oxidation Products", J. Ruzicka et al., J. Chromatogr. 30(1),
92-9 (1967); Chem. Abs. 68, 21155y (1968).
(149) "The Gas-Chromatographic Determination of Organophosphorus Pesticides.
II. A Comparative Study of Hydrolysis Rates", J. H. Ruzicka et al.,
J. Chromatogr. 31(1), 37-47 (1967); Chem. Abs. 68, 2191r (1968).
(150) "Gas-Liquid Chromatographic Separation of Some Organophosphate
Pesticides, Their Hydrolysis Products, and Oxons", I. H. Suffett
et al., Environ. Sci. Technol. 1(8), 639-43 (1967); Chem. Abs. 67,
107614p (1967).
•
(151) "Thin-Layer Chromatographic Detection and Quantitative Determination
of Malathion in Biological Materials", A. Farago, J. Forensic Sci.
12(4), 547-8 (1967); Chem. Abs. 68, 38508p (1968).
(152) "Systematic Applications of Gas-Liquid Chromatography in Toxicology.
V. Pesticides and Evaluation of Toxic Levels", N. C. Jain et al.,
Microchem. J. 12(2), 265-72 (1967); Chem. Abs. 67, 42144p (1967).
(153) "Malathion Inhibition of Esterases as a Determinant of Malathion
Toxicity", S. D. Murphy, J. Pharmacol. Exp. Ther. 156(2), 352-65
(1967); Chem. Abs. 67_, 10660n (1967).
(154) "Thin-Layer Chromatographic Separation Scheme for Insecticidally
Active Phosphoric Acid Esters", J. A. Guth, Pflanzenschutzberichte
35(9-10), 129-43 (1967); Chem. Abs. 67, 72784q (1967).
(155) "Gas-Chromatographic Determination of Parathion and Malathion",
S. Yoshida, Else! Kagaku 13(5), 254-7 (1967); Chem. Abs. 68, 94857p
(1968).
147
-------
(156) "The Stability of Organophosphorus Pesticides. II. Relation of
Thermally Accelerated Degradation Test to Stability of Organophosphorus
Pesticide Dust Formulation", H. Takehara et al. , Nippon Nogei Kagaku
Kaishi 41(5), 203-8 (1967); Chem. Abs. 67., 81418a (1967).
(157) "Methods for Analyzing Organophosphorus Insecticides (Trichlorometaphos-
3 and Carbophos) in Aerosol Balloons and in Air", G. G. Gonskaya et al.,
Tr. Tsent. Nauch.-Issled. Dezinfek. Inst. , No. 18 (Pt. 3), 21-4 (1967);
Chem. Abs. J70_, 2685w (1969).
(158) "Separation and Identification of Some Organophosphate Insecticides
by Thin-Layer Chroma tography and Their Determination After Conversion
into Orthophosphate" , Pantovic, Hrana Ishrana, 8(11-12), 769-71 (1967);
> Chem. Abs. 69, 66429c (1968).
1968
(159) "Enzymic Detection of Ten Organophosphorus Pesticides and Carbaryl
on Thin-Layer Chromatograms : An Evaluation of Indoxyl, Substituted
Indoxyl, and 1-Naphthyl Acetates as Substrates of Esterases", C. E.
Mendoza et al. , Analyst (London) 93 (1102), 34-8 (1968); Chem. Abs.
6£, 58668u (1968).
(160) "Consistency of Rgt Values of Six Organophosphorus Pesticides Resolved
by Thin-Layer Chroma tography in the Presence of Plant Extracts Without
Elaborate Clean-up", C. E. Mendoza et al. , Analyst (London), 93(1111),
688-90 (1968); Chem. Abs. 70, 10566y (1968).
(161) "Procedure for Semiquantitative Confirmation of Some Organophosphorus
Pesticide Residues in Plant Extracts", P. J. Wales et al., Analyst
(London) 93(1111), 691-3 (1968); Chem. Abs. 70, 10567z (1969).
(162) "Nuclear Magnetic Resonance Studies of Phosphorus (V) Pesticides. I.
Chemical Shifts of Protons as a Means of Identification of Pesticides",
H. Babad et al. , Anal. Chlm. Acta 41(2), 259-68 (1968); Chem. Abs.
68, 77181w (1968).
(163) "Collaborative Study of Three Gas Chromatographic Dual Detection
Systems for Analysis of Multiple Chlorinated and Organophosphorus
Pesticides", J. R. Wessel, J. Ass. Offic. Anal. Chem. 51(3), 666-75
(1968); Chem. Abs. 69, 9900a (1968).
(164) "High-Resolution N.M.R. Spectra of Pesticides. I. Organophosphorus
Pesticides", L. H. Keith et al. , J. Ass. Offic. Anal. Chem. 51(5),
1063-94 (1968); Chem. Abs. 69, 75849s (1968).
(165) "Sodium Methylate Treatment of Cleaned Up Plant Extracts in Confirma-
tion of Some Pesticide Residues by Gas-Liquid and Thin-Layer
Chroma tography" , C. E. Mendoza et al., J. Assoc. Offic. Anal. Chem.
51(5), 1095-101 (1968); Chem. Abs. 69, 75626s (1968).
148
-------
(166) "Thin-Layer Chromatography of Organophosphorus Insecticides with
Several Adsorbents and Ternary Solvent Systems", M. E. Getz et al.,
J. Ass. Offie. Anal. Chem. 51(5), 1101-7 (1968); Chem. Abs. 6£,
75850k (1968).
(167) "Versatility of OV-17 Substrate for Gas Chromatography of Pesticides",
C. A. Bache et al., J. Ass. Offie. Anal. Chem. 51(6), 1270-1 (1968);
Chem. Abs. 70, 27907h (1969).
(168) "Microwave-Powered Emission Determination of Residues of Organic
Bromine, Chlorine, Iodine, Phosphorus, and Sulfur Pesticides in a
Helium Plasma", C. A. Bache et al., Biomed. Appl. Gas Chromatogr.
2, 165-78 (1968); Chem. Abs. _73, 76019r (1970).
(169) "Cleanup Procedure for Water, Soil, Animal, and Plant Extracts for
the Use of Electron-Capture Detector in the Gas Chromatographic
Analysis of Organophosphorus Insecticide Residues", A. M. Kadoum,
Bull. Environ. Con tarn. Toxicol. 3(4), 247-53 (1968); Chem. Abs. 69.,
75644w (1968).
(170) "The Effect of the Column Support Material on the Gas-Chromatographic
Resolution of Methyl Parathion, Ethyl Parathion, Ethyl Para-oxon,
Malathion, and Lalaoxon", A. Bevenue et al., J. Chromatogr. 35(1), 17-
23 (1968).
(171) "Design and Evaluation of a Three-Electrode Thermionic Detector",
F. P. Speakman et al., Column 2(3), 2-8 (1968); Chem. Abs. 73, 65302b
(1970).
(172) "Gas Chromatographic Determination of Diethyl Fumarate in Malathion
Extracts and Preparations Used for Control of Body Lice", F. Acree,
Jr. et al., J. Econ. Entomol. 61(2), 457-9 (1968); Chem. Abs. 68,
lOAlllg (1968).
(173) "Polyamide Layer Chromatography of Organophosphorus Pesticides",
J. T. Huang et al., J. Pharm. Sci. 57(9), 1620-1 (1968); Chem. Abs.
69, 85652m (1968).
(174) "Automated Differential Screening Method for Organophosphorus Pesti-
cides", D. C. Leegwater et al., J. Sci. Food Agr. 19(9), 513-18
(1968); Chem. Abs. 69, 95147q (1968).
(175) "Nuclear Magnetic Resonance Studies of Phosphorus (V) Pesticides.
III. Hydrolysis of Aliphatic Pesticides by Aqueous Solutions", M. C.
Goldberg et al., U. S. Geol Surv., Prof. Pap. No. 600-D, 20-3 (1968);
Chem. Abs. 7<), 67155t (1969).
(176) "The Use of Gas Chromatography with Electron Capture in the Analysis
of Organophosphate Pesticides", M. Salame, Ann. Biol. Clin. (Paris)
26(7-9), 1011-21 (1968); Chem. Abs. 69, 105280u (1968).
149
-------
(177) "Detection of Pesticides by Reversed Phase Paper Chronatography",
R. T. Want et al., Chung Kuo Mung Yeh Hua Hsueh Bui Chih 6(3-4),
63-8 (1968); Chem. Abs. 71, 111799c (1969).
(178) "Use of an Electron-Capture Detector in Gas Chromatography. III.
Example of Its Application. Study of the Response of Some Chlorinated
and Phosphorylated Pesticides", P. Devaux et al., Bull. Soc. Chim. Fr.
(4). 1627-33 (Fr) (1968); Chem. Abs. 69, 26229f (1968).
(179) "Detection of Thio- and Dithiophosphoric Esters and Esterase Inhibitor
on Thin-Layer Chromatograms", H. Beitz et al., Z. Chem. 8(10), 387-8
(1968); Chem. Abs. _70, 10612k (1969).
(180) "Microanalysis of Some Organophosphorus Pesticides by a Spectrophoto-
metric Method Using Safranine Reagent", K. Suzuki et al., Bunseki
Kagaku 17(10), 1279-83 (1968); Chem. Abs. 70, 27904e (1969).
(181) "Qualitative Analysis of Synthetic Organic Pesticides by Spot Tests",
M. Kanda et al., Nippon Hoigaku Zasshi 22(3), 229-51 (1968); Chem.
Abs. 2i, 65726x (1970).
(182) "Industrial Hygiene and Health Status of Workers Engaged in the Produc-
tion of Carbophos", V. N. Trefilov et al., Gig. Tr. Prof. Zabol. 12(4),
7-11 (1968); Chem. Abs. 69, 29947z (1968).
(183) "0,0-Dimethyl S-(l,2-Dicarboethoxyethyl) Dithiophosphate", Romania,
Ministry of the Chemical Industry, U. S. 3,403,201, 24 Sept. 1968;
Chem. Abs. 70, 3302f (1969).
(184) "0,0-Dimethyl Phosphorodithioate of Diethyl Mercaptosuccinate (Malathion)",
American Cyanamid Co., Brit. 1,126,264, 05 Sept. 1968; Chem. Abs. 70.
37211r (1969).
(185) "Diethyl Mercaptosuccinate 0,0-Dimethyl Phosphorodithioate (Malathion)",
American Cyanamid Co., Fr. 1,541,883, 11 Oct. 1968; Chem. Abs. 71,
90858d (1969).
(186) "Determination of Carbophos", T. B. Beider, U. S. S. R. 233,991, 24
Dec. 1968; Chem. Abs. _71» 2*34j (1969).
1969
(187) "Identification of Pesticides in Mixtures by High-Resolution Mass
Spectrometry", R. E. Lovins, Chem. 17(3), 663-7 (1969); Chem. Abs.
71, 29523z (1969).
(188) "Identification and Determination of Prganophosphorus and Carbamate
Insecticides by Thin-Layer Chromatography", M. Ramasamy, Analyst
(London), 94(1125), 1075-80 (1969); Chem. Abs. 72, 77836w (1970).
150
-------
(189) "Supplementary Interpretations of the H.M.R. Spectra of Phosphorus
Pesticides", L. H. Keith et al., Anal. Chlm. Acta 44(2), 447-8 (1969);
Chem. Abs. 70, 76682q (1969).
(190) "Pesticide Residues. Recovery of 65 Organophosphorus Pesticides from
Florisil with a New Solvent-Elution System", H. Beckman et al., J. Ass.
Offic. Anal. Chem. 52(2), 286-93 (1969); Chem. Abs. JW, 86520z (1969).
(191) "Alkaline Precolumn for Use in Gas-Chromatographic Pesticide Residue
Analysis", 6. A. Miller et al., J. Ass. Offic. Anal. Chem. 52(3), 548-53
(1969); Chem. Abs. 71, 12021m (1969).
(192) "Collaborative Study of Confirmative Procedures by Single-Sweep
Oscillographic Polarography for the Determination of Organophosphorus
Pesticide Residues in Nonfatty Foods", R. J. Gajan, J. Ass. Offic.
Anal. Chem. 52(4), 811-17 (1969); Chem. Abs. 71, 79813q (1969).
(193) "Polyamide-Layer Chromatography of Organophosphorus Pesticides",
K. Nagasawa et al., J. Chromatogr. 39(3), 282-90 (1969); Chem. Abs.
70, 114093h (1969).
(194) "Identification of Organophosphate Pesticides by Gas Chromatography
with the Flame Photometric Detector", C. W. Stanley et al., J. Chromatogr.
40(2), 289-93 (1969); Chem. Abs. 70, 114094J (1969).
(195) "Simple and Rapid Separation of Pesticides by Polyamide Chromatography",
R. I. Wang et al., J. Chromatogr. 42(3), 416-18 (1969); Chem. Abs. 7±,
59980p (1969).
(196) "Gas-Liquid Chromatography of Pesticides on OV-17 Stationary Phase",
V. Leoni et al., J. Chromatogr. 43(3), 388-91 (1969); Chem. Abs. 71,,
116424m (1969).
(197) "Thin-Layer Chromatographic-Enzymic Detection of Organophosphorus
Insecticides. Thin-Layer Chromatographic Behavior of Some Other
Insecticides", H. Ackermaim, J. Chromatogr. 44(2), 414-18 (1969);
Chem. Abs. 72, 77910r (1970).
(198) "Field lonization Spectra of Some Pesticidal and Other Biologically
Significant Compounds", J. N. Damico et al., Int. J. Mass Spectrom.
Ion Phys. 2(2), 161-82 (1969); Chem. Abs. 70, 105767d (1969).
(199) "Determination of Organophosphorus Pesticides in Water", C. Zweig
et al., Residue Rev. 26, 17-36 (1969); Chem. Abs. .71, 80107u (1969).
(200) "Chemical and Thermal Methods for Disposal of Pesticides", M. V.
Kennedy et al., Residue Rev. 29, 89-104 (1969); Chem. Abs. 72,
53996x (1970).
151
-------
(201) "Nature of the Yellow Copper Complex Produced in Certain Analytical
Methods for the Determination of Malathion", A. C. Hill, J. Sci.
Food Agr. 20(1), 4-7 (1969); Chem. Abs. 70, 56624u (1969).
(202) "Chromatographic Determination of Trace Amounts of Pesticide Residues",
M. Beroza et al., Trace Subst. Environ. Health-3, Proc. Univ. Mo.
Annu. Conf., 3rd, 331-51 (1969); Chem. Abs. 74_, 2963t (1971).
(203) "Simple and Rapid Reversed Phase Thin-Layer Chromatography of
Pesticides", R. T. Wang et al., Hua Hsueh (4), 80-5 (1969); Chem.
Abs. 74, 2953q (1971).
(204) "Isolation of Pesticide Traces from Water", F. Herzel, Staedtehygiene
20(12), 301-9 (1969); Chem. Abs. 72, 120361b (1970).
(205) "Analysis of Chlorinated and Organic Phosphorus Pesticides by Gas
Chromatography", M. Kanda et al., Nippon Hoigaku Zasshi 23(6), 477-
86 (1969); Chem. Abs. 73 (1970).
(206) "Determination of Chlorinated Insecticides by a Gas-Liquid Chromato-
graphic Method", V. V. Ermakov, Zh. Anal. Khim. 24(8), 1264-70
(1969); Chem. Abs. _72_, 2468j (1970).
(207) "Phosphorothioates", Mobil Oil Corp., U.S. 3,470,272, 30 Sept. 1969;
Chem. Abs. 71, 123554g (1969).
(208) "0,0-Dimethyl S-(1,2-Dicarbethoxyethyl) Dithiophosphate", J. Macko
et al., Czech. 132,856, 15 Jun 1969; Chem. Abs. 73, 120077J (1970).
1970
(209) "Correlations Between Phosphorus-31 NMR Chemical Shifts and Structures
of Some Organophosphorus Pesticides", R. T. Ross et al., Anal. Chlm.
Acta 52(1), 139-41 (1970); Chem. Abs. .74, 31000g (1971).
(210) "GLC [Gas-Liquid Chromatographic] Retention Times of Pesticides and
Metabolites Containing Phosphorus and Sulfur on Four Thermally
Stable Columns", M. C. Bowman et al., J. Ass. Offic. Anal. Chem.
53(3), 499-508 (1970); Chem. Abs. _73 (1970).
(211) "Microcolumn Chromatographic Cleanup for the Analysis of Pesticides
in Water", L. M. Law et al., J. Ass. Offic. Anal. Chem. 53(6), 1276-
86 (1970); Chem. Abs. 74, 2
-------
(213) "Modified Enzymic Detection Method for Thin-Layer Chromatograms of
Pesticides", G. F. Ernst et al., J. Chromatogr. 49(2), 325-8 (1970);
Chem. Abs. _73, 76024p (1970).
(214) "Proton Magnetic Resonance Studies on Organophosphorus Pesticides.
I. Doubling of Resonances Induced by Asymmetry", Z. L. F. Gaibel
et al., Va. J. Sci. 21(1), 14-16 (1970); Chem. Abs. 73, 71883h (1970).
(215) "Residue Analyses of Phosphorus-Containing Insecticides with a Filter-
Flame Photometer", H. Haub et al., Deut. Lebensm.-Rundsch 66(10),
317-22 (1970); Chem. Abs. 73, 130055q (1970).
(216) "0,0-Dimethyl S-(l,2-Dicarbethoxyethyl) Dithiophosphate", J. Macko
et al., Czech. 135,413, 15 Feb 1970; Chem. Abs. 74, 111556h (1971).
(217) "Insecticidal Phosphorodithioates", Badische Anilin- und Soda-Fabrik
A.-G. Ger. Offen. 1,923,269, 19 Nov 1970; Chem. Abs. 74, 4l901r (1971).
1971
(218) "Hazards from Fires Involving Organophosphorus Insecticides", W. M.
Smith, Jr. et al., Amer. Ind. Hyg. Ass. J., 32(7), 468-74 (1971);
Chem. Abs. .76, 21705t (1972).
(219) "Infrared and Ultraviolet Spectra of Seventy-Six Pesticides", R. C.
Gore et al., J. Ass. Offic. Anal. Chem. 54(5), 1040-82 (1971); Chem.
Abs. 25, 117202g (1971).
(220) "Removal of Sulfur in Environmental Samples Prior to Gas Chromato-
graphic Analysis for Pesticide Residues", R. L. Schutzmann et al.,
J. Ass. Offic. Anal. Chem. 54(5), 1117-19 (1971); Chem. Abs. 76,
757w (1972).
(221) "Method for Confirmation of Organophosphorus Compounds at the Residue
Level", M. T. Shafik et al., Bull. Environ. Contain. Toxicol. 6(1),
55-66 (1971); Chem. Abs. 74, 124014e (1971).
(222) "Malathion [0,0-Dimethyl S-l,2-di(ethoxy-carbamyl)-ethyl Phosphoro-
dithioate] Residues on Ladino Clover Seed Screenings Exposed to
Ultraviolet Irradiation", T. E. Archer, Bull. Environ. Contain.
Toxicol. 6(2), 142-3 (1971); Chem. Abs. 75_, 4526x (1971).
(223) "Rate of Hydrolysis of Seven Orgdhophosphate Pesticides", R. P.
Cowart et al., Bull. Environ. Contain. Toxicol. 6(3). 231-4 (1971);
Chem. Abs. 75, 97557w (1971).
(224) "Investigation of Flavones as Fluorogenic Spray Reagents for Organic
Compounds on a Cellulose Matrix. II. Detection of Pesticides",
V. Mallet et al., J. Chromatogr. 56(1), 69-77 (1971); Chem. Abs.
.74, 123973e (1971).
153
-------
(225) "Routine Method for the Determination of Organophosphorus Insecticides
by Thin-Layer Chromatography", 0. Antoine et al., J. Chromatogr. 58(2),
247-56 (1971); Chem. Abs. 25, 75234m (1971).
(226) "Separation of Fifty Pesticides and Related Compounds and Polychloro-
biphenyls into Four Groups by Silica Gel", V. Leoni, J. Chromatogr.
62(1), 63-71 (1971); Chem. Abs. JT6, 82034v (1972).
(227) "Rapid Thin-Layer Chromatographic Method for the Identification of
Organophosphates in Blood", D. M. Paez et al., Rev. Assoc. Bioquim.
Argent. 36(194-195), 127-31 (1971); Chem. Abs. 2i» 95346y (1972).
(228) "Malathion and Its Determination by Gas Chromatography", M. Dedde
et al., Chim. Anal. (Paris) 53(10), 620-8 (1971); Chem. Abs. 76,
55089k (1972).
(229) "Simultaneous Gas Chromatographic Determination of Chlorinated Hydro-
carbons and Organophosphates in Plant Material", G. Becker, Deut.
Lebensm.-Rundsch. 67(4), 125-6 (1971); Chem. Abs. 75_, 4460w (1971).
(230) "Esterase Inhibition Technique for the Detection of Organophosphorus
Pesticides on Thin-Layer Chromatograms", T. Stijve et al., Mitt. Geb.
Lebensmittelunters. Hyg. 62(1), 25-31 (1971); Chem. Abs. 75, 117195g
(1971).
(231) "Thin-Layer Chromatographic Analysis of Organophosphate Pesticides in
the Study of Environmental Contamination (Italian Surface Waters)M,
V. Leoni, Farmaco, Ed. Prat. 26(7), 383-93 (1971); Chem. Abs. 75,
128757t (1971).
(232) "Analytical Studies on Pesticides and Related Compounds. VI. Colorl-
metric Determination of S-Benzyl 0-Butyl S-Ethyl Phosphorodithioate
and Some Other Organophosphorus Pesticides", A. Murano et al.,
Bunscki Kagaku 20(6), 665-72 (1971); Chem. Abs. 75.» 97502z (1971).
(233) "Determination of Foschlor, Dichlorfos (DDVP), and Malathion in Water
by Thin-Layer Chromatography", D. Zycinski, Roc. Panstw. Zakl. Big.
22(2), 189-94 (1971); Chem. Abs. 75, 75235n (1971).
(234) "Determination of Malathion in the Air", D. Colosi-Esca, Igiena 20(5),
299-305 (1971); Chem. Abs. 2i» 37054v (1972).
(235) "Industrial Hygiene and State of Workers' Health During Carbophos
Production", V. S. Aizenshtad et al., Gig. Tr. Prof. Zabol. 15(3),
49-51 (1971); Chem. Abs. 74, 145951y (1971).
(236) "Purification of Technical Carbophos", K. D. Shvetsova-Shilovskaya
et al., Khim. Prom. (Moscow) 47(11), 869 .(1971); Chem. Abs. 76,
33745u (1972).
154
-------
(237) "Hygienic Characteristics of Working Conditions in Carbophos
Production", V. S. Aizenshtadt et al., Sb. Nauch. Tr., Kuibyshev.
Nauch.-Issled. last. Gig. No. 6, 61-3 (Russ) (1971); Chem. Aba. 78,
33453p (1973).
(238) "The p-Value Approach to Quantitative Liquid-Liquid Extraction of
Pesticides From Water. I. Organophosphates. Choice of pH and
Solvent", L. H. Suffet et al., J. Agr. Food Chem. 20(1), 52-6
(1972); Chem. Abs. 76_, 109005a (1972).
(239) "Analysis of Decomposition Products of Pesticides", M. V. Kennedy
et al., J. Agr. Food Chem. 20(2), 341-3 (1972); Chem. Abs. 77., 1629p
(1972).
(240) "Potentiation of Toxicity of Organophosphorus Compounds Containing
Carboxylic Ester Functions Toward Warm-Blooded Animals by Some Organo-
phosphorus Impurities", G. Pellegrini et al., J. Agr. Food Chem.
20(5), 944-50 (1972); Chem. Abs. 77., 160825r (1972).
(241) "Metallofluorescent Indicators as Spray Reagents for the In Situ
Determination of Organophosphorus Pesticides on Thin-Layer Chroma to-
grams", T. F. Bidleman et al., Anal. Chim. Acta. 60(1), 13-23 (1972);
Chem. Abs. 77., 84271q (1972).
(242) "Elution Solvent System for Florisil Column Cleanup in Organochlorine
Pesticide Residue Analyses", P. A. Mills et al., J. Ass. Offie. Anal.
Chem. 55(1), 39-43 (1972); Chem. Abs. 7_6, 71131y (1972).
(243) "Infrared Analysis of Pesticide Formulations", S. W. Goza, J. Ass.
Off. Anal. Chem. 55(5), 913-17 (1972); Chem. Abs. 77, 160898s (1972).
(244) "Nonaqueous Copper Colorimetric Method for Determination of Malathion
in Technical Grade Malathion and in Malathion Formulations", R. S.
Wayne et al., J. Ass. Off. Anal. Chem. 55(5), 926-38 (1972); Chem.
Abs. 77_, 160901n (1972).
(245) "Argentimetric Method for Determination of Malathion in Formulations",
J. W. Miles et al., J. Ass? Off. Anal. Chem. 55(5), 1133-41 (1972);
Chem. Abs. 7_7, 160909w (1972).
(246) "Effects of Four Lights on Malathion Residues on Glass Beads, Sorghum
Grain, and Wheat Grain", D. R. Mosher et al., J. Econ. Entomol. 65(3),
847-50 (1972); Chem. Abs. 77, 84474h (1972).
(247) "Chemical Hydrolysis of Some Organic Phosphorus and Carbamate Pesti-
cides in Aquatic Environments", S. D. Faust et al., Environ. Lett.
3(3), 171-201 (1972); Chem. Abs. 77_, 110352p (1972).
(248) "Chemical and Thermal Aspects of Pesticide Disposal", M. V. Kennedy
et al., J. Environ. Qual. 1(1), 63-5 (1972); Chem. Abs. 2£t 69170s
(1972).
155
-------
(249) "Mild Thermal Degradation of Pesticides", B. J. Stojanovlc et al.,
J. Environ. Qual. 1(4), 397-401 (1972); Chem. Abs. 78, 80904w (1973).
(250) "Determination of Malathion and Diethyl Maleate", L. Biro et al.,
Nehezvegyip. Kut. Intez. Kozlem. 4, 93-7 (1972); Chem. Abs. 78,
25070w (1973).
(251) "Analytical Studies on Pesticides and Related Compounds. XV.
Improved Determination of Several Organophosphorus Pesticides",
F. Yuki et al., Bunseki Kagaku 21(3), 375-8 (1972); Chem. Abs. 72.*
44149z (1972).
(252) "Determination of Malathion and Malaoxon in Fruits and Vegetables",
J. Zadrozinska, Rocz. Panstw. Zakl. Big. 23(1), 23-8 (1972); Chem.
Abs. _76, 152127d (1972).
1972
(253) "Use of Thin-Layer Chromatography to Determine Selected Organophosphorus
Insecticides (Fenthion, Fenitrothion, and Malathion) in Soil",
K. Cywinska-Smoter, Rocz. Panstw. Zakl. Hig. 23(5), 505-12 (1972);
Chem. Abs. 7J&, 39090q (1973).
(254) "Results of Analysis of Technical Malathion by Three Methods: Colorimetry,
IR Spectrophotometry, and Gas-Liquid Chromatography", 6. Baluja, et al.,
Rev. Agroquim. Technol. Aliment. 12(4), 577-82 (1972); Chem. Abs. 78.
155332u (1973).
(255) "Determination of Some Organothiophosphorus Pesticides with Palladium
Chloride Following Their Separation by Thin-Layer Chromatography",
D. A. Jovanovic et al., Acta Pharm. Jugoslav 22(3), 91-6 (1972);
Chem. Abs. 78_, 2806b (1973).
(256) "Gel Filtration Cleanup for Multiresidues of Organophosphorus Pesti-
cides in Rice", Z. Masud et al., Pestic. Sci. 4(1), 131-6 (1973);
Chem. Abs. 78, 70303k (1973).
156
-------
METHOMYL
1964
(1) "Synthesis of Thiohydroximates. The Addition of Thiols to Nitrile
Oxides", M. H. Benn, Can. J. Chem. 4£ (11), 2393-7(1964); Chem. Abs.
62, 475a (1965).
1968
(2) "EPN-hydroxamate Insecticidal Mixtures", du Pont de Nemours, E. I.,
and Co., U.S. 3,414,652, December 3, 1968; Chem. Abs. 70, 56708z
(1969).
1968
(3) "Hydroxamoyl Chlorides", du Pont de Nemours, E. I., and Co., S. African
6,706,406, March 4, 1968; Chem. Abs. 2P_, 57112n (1969).
1968
(4) "Insecticidal Activity of Some Oxime Carbamates", J. C. Felton, J. Sci.
Food Agr. 1968; Chem. Abs. 2P_t 67128m (1969).
1968
(5) "Du Pont Lannate, Methorny1 Insecticide", G. A. Roodhans, et al., Meded.
Rijksfac. Landbouwwetensch., Gent.1968, 33(3), 833-8; Chem. Abs. 71,
60078g (1969).
1970
(6) "N-Hydroxythioacetimidates", du Pont de Nemours, E. I., and Co., S.
African 69 08,442, June 24, 1970; Chem. Abs. 74, 76043q (1971).
1971
(7) "Pesticidal Substituted 0-carbamylhydroxamates", du Pont de Nemours,
E. I., and Co., April 27, 1971; Chem. Abs. 75, 19985v (1971).
1972
(8) "Direct Gas Chromatographic Determination of Methomyl (Lannate) With
Mirocoulometric Nitrogen Detection", I. H. Williams, Pestic. Sci.
1972. 3(2), 179-81; Chem. Abs. 77., 57444s (1972).
1972
(9) "Pesticidal Substituted 0-carbamaoylhydroxamates", du Pont de Nemours,
E. I., and Co., U.S. 3,647,861, March 7, 1972; Chem. Abs. 77., 57612v
(1972).
157
-------
1972
(10) "Analytical Studies on Pesticides and Related Compounds. XVIII. Deter-
mination of S-methyl-N-(methylcarbamoyloxy)thioacetimidate (methomyl)"
Murano, Bunseki Kagaku 1972, 21(6), 804-6; Chem. Abs. 77.. 136119t (1972).
1973
(11) "Determination of Some Carbamates by Enzyme Inhibition Techniques Us-
ing Thin-layer Chromatography and Colorimetry", C. E. Mendoza, J. Agr.
Food Chem. 1973; Chem. Abs. 79. 14275m (1973).
1973
(12) "Substituted 0-carbamoylhydroxamates", du Pont de Nemours, E. I., and Co.,
U.S. 3,726,908, April 10, 1973; Chem. Abs. 7£, 18164x (1973).
1973
(13) "Carbamates of Alkythiolhydroxamates and Intermediates", du Pont de
Nemours, E. I., and Co., U.S. 3,752,841, August 14, 1973; Chem. Abs.
79, 91630a (1973).
158
-------
METHYL PARATHION
1950
1. "Synthesis and Development of Parathion and Related Compounds",
J. T. Cassaday, et al., Ibid. 143-9, Advances in Chemistry Science,
No. 1, 273 pp., 1950, American Chemical Society; Chem. Abs. 44,
7009 (1950).
2. "Organic Phosphorus Insecticides", S. A. Hall, et al., Ibid. 150-9;
Chem. Abs. 44_, 7009 (1950).
3. "Methyl Homolog of Parathion", S. A. Hall, J. Am. Chem. Soc. 72,
2768-9 (1950); Chem. Abs. 44, 10673 (1950).
4. "Chemical Studies of Insecticides. II. The Hydrolysis of 0,0-
diethyl- and 0,0-dimethyl-O-p-nitrophenyl Thiophosphates", J. A. A.
Ketelaar, Rec. trav. chim. 69, 649-58(1950); Chem. Abs. 44. 10471
(1950).
5. "The Analysis of Phosphate Esters. I. The Pure Material", P.
Reckendorfer, Pflanzenschutzber 5, 287-95(1950); Chem. Abs. 48,
11248 (1950).
1952
6. "Potentiometric Determination of 0,0-diethyl- 0-p-nitrophenyl
Thiophosphate (E 605) or 0,0-dimethyl 0-p-nitrophenyl Thiophosphate
in Commercial Preparations", M. Schonamsgruber, Z. anal. Chem. 135,
23-36(1952); Chem. Abs. 48, 3851 (1952).
1954
7. "Paper Chromatography of Some Organic Phosphate Insecticides. I.
New Spot Test", J. W. Cook, J. Assoc. Offie. Agr. Chemists 37,
984-7(1954); Chem. Abs. 49, 2665 (1954).
8. "Paper Chromatography of Some Organic Phosphate Insecticides. II.
Separation and Identification", J. W. Cook, J. Assoc. Offie. Agr.
Chemists 37, 987-9(1954); Chem. Abs. .49, 2665 (1954).
1955
9. "Spectrophotometric Determination of Morphine, Methyl-parathion, and
Metasystox, and Diffusion Analysis of Cyanide", T. Takemura, Science
and Crime Detection (Japan) 8, No. 3, 68-74(1955); Chem. Abs. 50,
6258 (1955).
159
-------
1956
10. "Thermal Decomposition of Some Fhosphorothioate Insecticides", J. B.
McPherson, Jr., et al., J. Agr. Food Chem. 4, 42-9(1956); Chem. Abs.
50, 4446 (1956).
1957
11. "The Analysis of Thiophosphoric Acid Ester Preparations", H. Meltzer,
Nachrbl. deut. Pflanzenschutzdienst (Berlin) 11, 178-80(1957); Chem.
Abs. 54_, 6392 (1957).
12. "Rapid Method to Identify Dimethylparathion in the Presence of
Diethylparathion", V. Toubol, Ann. fals. et fraudes 50, 336-7(1957);
Chem. Abs. 52, 5728 (1957).
13. "Determination of Residual Metaphos in Vegetable Food Products",
N. M. Rusin, Inform. Byull. Moskov. Inst. Sanit. 1 Gigieny 1957,
No. 10-11, 11-13; Chem. Abs. 52_, 20754 (1957).
1958
14. "Purification of Effluents in the Manufacture of 0,0-diethyl-O-
(4-nitrophenyl)-thiophosphate", N. N. Mel'nikov, et al., Org.
Insektofungitsidy i Gerbitsidy 1958, 60-4; Chem. Abs. 54_, 10221 (1958)
15. "Determination of E 605 (Parathion) and Methyl-E 605 in Air", W.
Pilz, Mikrochim. Acta 1958, 383-94; Chem. Abs. 53, 20639 (1958).
16. "Titrimetric Method for Measuring the Cholinesterase Activity of
Blood Serum and Its Application to the Microdetencination of Some
Cholinesterase Inhibitors", R. M. Fournier, Mem. poudres 40,
403-12(1958); Chem. Abs. 55, 668 (1958).
17. "Isolation of 0,0'-diethyl and 0,0'-dimethyl 0-(p-nitrophenyl)
Thiophosphate from Aqueous Liquids", E. Scheibe, et al., Pharmazie
13, 262-6(1958); Chem. Abs. .53, 1215 (1958).
18. "Separation and Identification of Chlorinated Organic Pesticides
by Paper Chromatography. XI. A Study of 114 Pesticide Chemicals:
Technical Grades Produced in 1957 and Reference Standards", L. C.
Mitchell, J. Assoc. Offic. Agr. Chemists 41, 781-816(1958); Chem.
Abs. 53, 2525 (1958).
1959
19. "Chemical Studies of Organophosphorus Insecticides. IV. Rate of
Hydrolysis of Some Organophosphates", R. Sato, et al., Botyu-Kagaku
24, 89-93(1959); Chem. Abs. 60, 7384 (1959).
160
-------
1960
20. "Aging Tests on Emulsifiable Concentrates of Organo Phosphorus
Insecticides", R. Okada, et al., Noyaku Seisan Gijutsu No. 3, 33-6
(1960); Chem. Abs. 55, 14803 (1960).
21. "Thiophos and Methaphos", N. N. Mel'nikov, et al., U.S.S.R.
126,880, Mar. 10, 1960; Chem. Abs. 54, 19597 (1960).
1961
22. "Determination of Phosdrin or Methylparathion in Formulations",
T. T. White, et al., J. Assoc. Offic. Agr. Chemists 44, 589-91(1961);
Chem. Abs. 55_, 23907 (1961).
23. "The Effect of Ultraviolet Light (2537 A.) on 141 Pesticide
Chemicals by Paper Chromatography", L. C. Mitchell, J. Assoc.
Offic. Agr. Chemists 44, 643-712(1961); Chem. Abs. 56, 3849 (1961).
24. "lexicological Detection and Determination of Thiophosphorlc Acid
Esters. II.", R. Fischer, et al., Pflanzenschutz Ber. 27, 165-76
(1961); Chem. Abs. , 5677 (1961).
25. "Identification of Methylparathion", S. Takagi, Ragaku Reisatsu
Renkyusho Hokoku 14, 226-32(1961); Chem. Abs. 56., 6415 (1961).
26. "Paper Chromatography of Parathion and Related Compounds Using
Filter Paper Impregnated with Silicic Acid", T. Niwase, Ragaku
Reisatsu Renkyusho Rokoku 14, 416-8(1961); Chem. Abs. 57., 2625
(1961).
27. "Column for the Continuous Contact of Immiscible Substances",
Monsanto Chemical Co., U.S. 2,976,310, Mar. 21, 1961; Chem. Abs.
55, 13948 (1961).
1962
28. "The Promising Utility of Infrared Assay of Pesticides and Their
Residues. II.", R. C. Blinn, et al., Pesticide Res. Bull. 2(4),
3-11(1962); Chem. Abs. 60, 13811 (1962).
29. "Synthesis of Metaphos", Guk-Nok Rwong, et al., Chosun Rwahakwon
Tongbo No. 2, 38(1962); Chem. Abs. 58, 11252 (1962).
30. "Paper-chromatographic Studies on the Effect of Ultraviolet Light
on Parathion and Its Derivatives", P. Roivistoinen, et al., Acta
Agr. Scand. 12, 267-76 (1962); Chem. Abs. 59, 4492 (1962).
31. "Detection and Determination of Phosphate-Ester Insecticides in
Plant Materials", E. Sandi, et al., Elelmiszervizsgalati Rozlemeny
8(1-2), 17-27(1962); Chem. Abs. 64, 8866 (1962).
161
-------
1962
32. "Polarographic Differentiation of Ethyl Parathion, Methyl Parathion,
and EPN", K. Hasegawa, Kagaku Reisatsu Kenkyusho Kokoku 15, 62-4
(1962); Chem. Abs. 5£, 6360 (1962).
33. "Polarographic Identification of Insecticides", H. Yamano, et al.,
Kagaku Keisatsu Kenkyusho Hokoku 15, 65-7(1962); Chem. Abs. 57,
6360 (1962).
34. "Analysis of Insecticides. I. Separation and Identification of
Parathion and Its Related Compounds by Chromatography", S. Inoue,
Kagaku Keisatsu Kenkyusho Hokoku 15, 68-70(1962); Chem. Abs. 57.
6360 (1962).
35. "Colorimetric Method for Determination of Parathion and Methyl-
parathion Residues on Some Fruits and Vegetables", J. Zadrozinska,
Roczniki Panstwowego Zakludu Hig. 13, 277-86(1962); Chem. Abs. 57.
14241 (1962).
36. "Separation and Determination of Organophosphorus Insecticides in
Vegetable Foods", G. Ya. Isaeva, et al., Vopr. Pitaniya 21, No. 6,
64-7(1962); Chem. Abs. .59, 14496 (1962).
37. "Stabilized Pesticidal Compositions", Stauffer Chemical Co., U.S.
3,060,083, Oct. 23, 1962; Chem. Abs. _58, 1874 (1962).
1963
38. "Thin-layer Chromatography for Insecticide Analysis", K. C. Walker,
et al., J. Assoc. Offic. Agr. Chemists 46, 250-61(1963); Chem. Abs.
58, 14626 (1963).
39. "The Analysis of Micro Amounts of Binapacryl, EPN, MethyIparathion,
and Parathion", D. A. George, J. Assoc. Offic. Agr. Chemists 46(6),
960-3(1963); Chem. Abs. 60, 4711 (1963).
40. "Analysis of Organophosphorus, Organochlorine Insecticide Residues
in Food by Gas Chromatography", T. Nishimoto, et al., Shokuhin
Eiseigaku Zasshi 4, 192-7(1963); Chem. Abs. , 4690 (1963).
41. "Stable Thiophosphate and Thiophosphite Composition", Chemagro
Corp., U.S. 3,089,807, May 14, 1963; Chem. Abs. 59_, 9259 (1963).
42. "Stabilization of Insecticides", Monsanto Chemical Co., U.S.
3,095,351, June 25, 1963; Chem. Abs. 59, 13291 (1963).
t ™"^
43. "Decolorizing and Purifying 0,0-dialkylthiophosphoryl Chlorides
and Thiophosphate Condensates Formed Therefrom", American Cyanamid
Co., U.S. 3,098,866, July 23, 1963; Chem. Abs. 60, 408 (1963).
162
-------
1964
44. "Gas Chromatography Retention Times and Sensitivity Data for
Insecticides and Herbicides", E. J. Bonelli, et al., J. Agr. Food
Chen. 12(4), 333-6 (1964); Chem. Abs. 61, 7635 (1964).
45. "Collaborative Comparison of Colorimetric and Potentiometric Methods
for Parathion and Methyl Parathion in Formulations", K. Helrich,
J. Assoc. Office Agr. Chemists 47(2), 242-4(1964); Chem. Abs. 60.
16441 (1964).
46. "Thin-layer Chromatography of Organophosphorus Pesticides and Acids
on Microchromatoplates", C. W. Stanley, J. Chroma tog. 16(3),
467-75(1964); Chem. Abs. .62, 11090 (1964).
47. "Detection and Separation of the Most Important Organophosphorus
Pesticides by Thin-layer Chromatography", M. Salame, J. Chromatog.
16(3), 476-80(1964); Chem. Abs. 62, 11090 (1964).
48. "Analyses of Organophosphorus Pesticides", W. P. McKinley, Proc.
Can. Soc. Forensic Sci. 2(2), 433-48(1964); Chem. Abs. 61, 7638
(1964).
49. "Thin-layer Chromatography in the Determination of Pesticide Residues",
R. A. Conkin, Residue Rev. 6, 136-61(1964); Chem. Abs. 61, 9976 (1964).
50. "The Use of Infrared Spectroscopy in the Analysis of Pesticide
Residues", N. T. Crosby, et al., Analyst 89(1058), 319-27(1964);
Chem. Abs. 61, 4891 (1964).
51. "The Detection of Organophosphorus Pesticides on Thin-layer
Chromatograms", P. J. Bunyan, Analyst 89(1062), 615-18(1964); Chem.
Abs. 61, 15282 (1964).
52. "The Effect of an Organophosphorus Cholinesterase Inhibitor
Methylparathion, Upon the Accumulation of Iodide by the Thyroid
Gland", H. Lybeck, et al., Ann. Acad. Sci. Fennicae Ser. A. V.
106(17), 8 pp.(1964); Chem. Abs. 61, 15282 (1964).
53. "The Determination of Traces of Phosphoric Esters by Oscillographic
Polarography", P. Nangniot, Anal. Chim. Acta 31(2), 166-74(1964);
Chem. Abs. 61, 12563 (1964).
54. "Pesticide Residues. Use of an Aerograph flame ionization Detector
as a Thermionic Detector. Application to Organophosphate Insecticide
Research", R. Mestres, et al., Trav. Soc. Pharm. Montpellier 24(4),
283-303(1964); Chem. Abs. 63, 13970 (1964).
55. "Method for Distinguishing Methyl from Ethyl Parathion and the
Quantitative Determination of Their Residues in Vegetative Products",
V. Ilkov, et al., Khim. i Ind. (Sofia) 36(4), 138-40(1964); Chem.
Abs. 61, 15259 (1964).
163
-------
1964
56. "Detection of Insecticldal Phosphoric Acid Esters and Their
Hydrolytic Cleavage Products", H. W. Rahn, et al., Pharmazie 19(9),
597-602(1964); Chem. Abs. 61, 16719 (1964).
57. "Determination of Some Organophosphorus Insecticides by Gas-Liquid
Partition Chromatography", M. Horiguchi, et al., Chem. Phann. Bull.
(Tokyo) 12(11), 1315-19(1964); Chem. Abs. j62, 5823 (1964).
58. "Evaluation of Minute Amounts of Some Phospho-organic Compounds in
Plant Material by Means of Paper Chromatography", J. Zadrozinska,
Roczniki Pantswowego Zakladu Hig. 15(1), 5-12(1964); Chem. Abs. ,
6262 (1964).
1965
59. "Thin-layer Chromatography and Cholinesterase Detection of Several
Phosphorothiono Insecticides and Their Oxygen Analogs", A. El-Refal,
et al., J. Agr. Food Chem. 13(5), 477-81(1965); Chem. Abs. £3_, 13968
(1965).
60. "Determination of Organophosphorus Insecticide Residues Using the
Emission Spectrometric Detector", C. A. Bache, et al., Anal. Chem.
37(12), 1477-80(1965); Chem. Abs. 64, 1288 (1965).
61. "An Approach to the Separation, Identification, and Determination
of at Least Ten Organophosphate Pesticide Residues in Raw Agricultural
Products", D. F. McCaulley, J. Assoc. Offie. Agr. Chemists 48(3),
659-65(1965); Chem. Abs. 63, 7564 (1965).
62. "Screening Procedure for Organothiophosphate Pesticide Residues on
Fruits and Vegetables Using Microcoulometric Gas Chromatography",
R. C. Nelson, J. Assoc. Offic. Agr. Chemists 48(4), 752-9(1965);
Chem. Abs. £3, 18932 (1965).
63. "Extraction p-values of Pesticides and Related Compounds in Six
Binary Solvent Systems", M. C. Bowman, et al., J. Assoc. Offic. Agr.
Chemists 48(5), 943-52(1965); Chem. Abs. 64, 4192 (1965).
64. "A Sweep Codistillation Cleanup Method for Organophosphate Pesticides.
I. Recoveries from Fortified Crops", R. W. Storherr, et al., J.
Assoc. Offic. Agr. Chemists 48(6), 1154-8(1965); Chem. Abs. 64, 8848
(1965).
65. "A Sweep Codistillation Cleanup Method for Organophosphate
Pesticides. II. Rapid Extraction Methods for Crops", R. R. Watts,
et al., J. Assoc. Offic. Agr. Chemists 48(6), 1158-60(1965); Chem.
Abs. 64, 8847 (1965).
164
-------
1965
66. "Polarographic Determination of Methylparathion in the Presence of
p-nitrophenol", Yao-Tung Huang, et al., Hua Hsueh Tung Pao 1965(6),
368-72; Chem. Abs. j>4, 8866 (1965).
67. "Two Methods of Biochemical Detection of Phosphorus-Containing
Insecticides on Thin-layer Chromatograms", R. Ortloff, et al., Z.
Chem. 5(10), 388-9(1965); Chem. Abs. 64., 7304 (1965).
68. "Gas-Liquid Chromatography of Organophosphorus Pesticides", J.
Kanazawa, et al., Agr. Biol. Chem. (Tokyo) 29(1), 56-60(1965);
Chem. Abs. 62, 12385 (1965).
69. "Determination of Selected Phosphoorganic Pesticides (Parathion,
Methylparathion, Diazinon, Malathion, Gusathion, Meta-Systox, and
Dipterex) by Thin-layer Chromatography Method", J. Zadrozinska,
Roczniki Panstwowego Zakladu Big. 16(4), 397-405(1965); Chem. Abs.
64, 2684 (1965).
70. "Toxicological Analysis of Organic Phosphorus Insecticides"; A.
Silva Santos, et al., Rev. Port. Farm. 15(3), 367-74(1965); Chem.
Abs. 64, 11794 (1965).
71. "Relation Between the Structure and Chromatographic Properties of
Organophosphorus Compounds", V. Batora, Khim. Primen. Fosfororg.
Soedin., Tr. Vses. Konf., 3rd 1965, 333-7; Chem. Abs. 77_, 74637 (1965)
72. "0,0-Dialkyl-O-aryl Thionophosphates", N. N. Mel'nikov, et al.,
U.S.S.R. 171,862, June 22, 1965; Chem. Abs. .63, 17972 (1965).
1966
73. "Gas Chromatographic Column for Pesticide Residue Analysis; Retention
Times and Response Data", J. A. Burke, et al., J. Assoc. Offic. Anal.
Chemists 49(2), 374-85(1966); Chem. Abs. j65_, 2894 (1966).
74. "Screening Procedure for Organothiophosphate Pesticide Residues on
Fruits and Vegetables by Microcoulometric Gas Chromatography", R.
C. Nelson, J. Assoc. Offic. Anal. Chemists 49(4), 763-6(1966); Chem.
Abs. 65, 17598 (1966).
75. "Mass Spectra of Some Organophosphorus Pesticide Compounds", J. N.
Damico, J. Assoc. Offic. Anal. Chemists 49(5), 1027-45(1966); Chem.
Abs. 66, 1833 (1966).
76. "Phosphorus Detector for Pesticides Analysis", C. H. Hartmann, Bull.
Environ. Contam. Toxicol. 1(4), 159-68(1966); Chem. Abs. 65, 17623
(1966).
165
-------
1966
77. "Determination of Organophosphorus Insecticide Residues Using
Cooke's Emission Spectroscopic Detector", C. A. Bache, et al.,
Residue Rev. 12, 35-44(1966); Chem. Abs. 65, 7895 (1966).
78. "Gas-chromatographic Separation of 0,0-dialkyl 0-(4-nitrophenyl)
Thiophosphates", J. Hrivnak, et al., Collection Czech. Chem.
Commun. 31(8), 3402-5(1966); Chem. Abs. 65, 12799 (1966).
79. "Thin-layer Chromatography of Pesticides", T. Salo, et al., Z.
Lebensm.-Untersuch. - Forsch. 129(3), 149-53(1966); Chem. Abs.
64, 20546 (1966).
80. "Analysis of Phenoxy Compounds. II. Paper Chromatographic
Detection of Several Active Substances with the Phenyl-ester
Group", R. Giebelmann, Pharmazie 21(3), 171(1966); Chem. Abs. 65,
5305 (1966).
81. "Methods for Market Control of Organophosphate Residues in Fruit
and Vegetables", Krause, Chr., Z. Pflanzenkr. Pflanzenschutz. 1966,
73(6), 335-45; Chem. Abs. .70, 18977 (1966).
82. "Determination of Parathion Residues in Lettuce", V. Chioffi,
Boll. Lab. Chim. Provinciali (Bologna) 17(2), 313-20(1966); Chem.
Abs. 65, 15976 (1966).
83. "Residue Analysis of Agricultural Chemicals. III. Electron-capture
Gas Chromatography of Various Pesticides", J. Kanazawa, et al.,
Nippon Nogei Kagaku Kaishi 40(4), 178-84(1966); Chem. Abs. 6»5,
4571 (1966).
84. "Gas Chromatographic Analysis of Pesticides. II. Gas Chromato-
graphic Determination of Organophosphorus Pesticides", H. Takehara,
et al., Nippon Nogei Kagaku Kaishi 40(11), 394-400(1966); Chem.
Abs. j>6, 94163 (1966).
85. "The Stability and Detection of Methylparathion (0,0-dimethyl 0-p-
nitrophenyl Phosphorothionate), an Organophosphorus Pesticide, in
Water", J.-Luczak, et al., Rocz. Panstw. Zakl. Big. 17(6), 517-21
(1966); Chem. Abs. 66, 94211 (1966).
1967
86. "Sweep Codistillation Cleanup of Fortified Edible Oils for
Determination of Organophosphate and Chlorinated Hydrocarbon
Pesticides", R. W. Storherr, et al., J. Ass. Offic. Anal. Chem.
50(3), 605-15(1967); Chem. Abs. 67., 42620 (1967).
87. "Direct Fluorescent Detection of Organothiophosphorus Pesticides
and Some of Their Sulfur-Containing Breakdown Products after Thin-
layer Chromatography", M. T. H. Ragab, J. Ass. Offic. Anal. Chem.
50(5), 1088-98(1967); Chem. Abs. 67, 99116 (1967).
166
-------
1967
88. "The Gas-chromatographic Determination of Organophosphorus Pesticides.
II. A Comparative Study of Hydrolysis Rates", J. H. Ruzicka, et al.,
J. Chromatogr. 31(1), 37-47(1967); Chem. Abs. 68_, 2197 (1967).
89. "Modified Hydrogen Flame-ionization Detector, Highly Sensitive and
Selective for Phosphates", R. V. Hoffman, Lect. Gas Chromatogr. 1966
1967, 137-47; Chem. Abs. 70, 95702 (1967).
90. "Thin-layer and Gas Chromatographic Analysis of Parathion and Methyl
Parathion in the Presence of Chlorinated Hydrocarbons", F. K.
Kawahara, et al., J. Water Pollut. Contr. Fed. 39(3), 446-57(1967);
Chem. Abs. £7, 36188 (1967).
91. "Thin-layer Chromatographic Separation Scheme for Insecticidally
Active Phosphoric Acid Esters", J. A. Guth, Pflanzenschutzberichte
35(9-10), 129-43(1967); Chem. Abs. 67_, 72789 (1967).
92. "Gas Chromatographic Determination of Residues of E 605 Products
and Agritox in Plants and Soil Samples", E. Moellhoff, Pflanzenschutz-
Nachr. "Bayer" 1967, 20(2), 557-74; Chem. Abs. 70, 27727 (1967).
93. "Detection and Determination of Organosphosphorus Insecticides by
the Schoenemann Reaction", K. Lohs, et al., Z. Chem. 7(3), 106-7
(1967); Chem. Abs. 66, 104258 (1967).
94. "The Stability of Organophosphorus Pesticides. II. Relation of
Thermally Accelerated Degradation Test to Stability of Organophos-
phorus Pesticide Dust Formulation", H. Takehara, et al., Nippon
Nogei Kagaku Kaishi 41(5), 203-8(1967); Chem. Abs. 67^, 81418 (1967).
95. "Determination of Some Organophosphorus Compounds in Biological
Material by a Paper Chromatographic Method", R. V. Mishina, Sud.-Med.
Ekspert. Kriminalistika Sluzhbe Sledstviya 1967, No. 5, 651-4; Chem.
Abs. .73, 76024 (1967).
96. "Preparation of 0, 0-dialkyl 0-aryl Thiophosphates", Ya. A.
Mandel'baum, et al., U.S.S.R. 198,330, June 28, 1967; Chem. Abs.
68, 59266 (1967).
1968
97. "Detection of Cholinesterase-inhibiting Pesticides Following
Separation on Thin-layer Chromatograms", W. Winterlin, et al., J.
Agr. Food Chem. 1968, 16(5), 808-12; Chem. Abs. 69_, 95359 (1968).
98. "Enzymic Detection of Ten Organophosphorus Pesticides and Carbaryl
on Thin-layer Chromatograms: An Evaluation of Indoxyl, Substituted
Indoxyl, and 1-naphthyl Acetates as Substrates of Esterases", C. E.
Mendoza, et al., Analyst (London) 93 (1102), 34-8(1968); Chem. Abs.
68, 58676 (1968).
167V
-------
1968
99. "Nuclear Magnetic Resonance Studies of Phosphorus(V) Pesticides.
I. Chemical Shifts of Protons as a Means of Identification of
Pesticides", H. Babad, et al., Anal. Chim. Acta 41(2), 259-68(1968);
Chem. Abs. 68, 77183 (1968).
100. "Collaborative Study of Three Gas Chromatographic Dual Detection
Systems for Analysis of Multiple Chlorinated and Organophosphorus
Pesticides", J. R. Wessel, J. Ass. Offic. Anal. Chem. 1968, 51(3),
666-75; Chem. Abs. 69_, 9902 (1968).
101. "High-resolution N.M.R. Spectra of Pesticides. I. Organophosphorus
Pesticides", I. H. Keith, et al., J. Ass. Offic. Anal. Chem. 1968,
51(5), 1063 94; Chem. Abs. 69_, 75835 (1968).
102. "Thin-layer Chromatography of Organophosphorus Insecticides with
Several Adsorbents and Ternary Solvent Systems", M. E. Getz, et al.,
J. Ass. Offic. Anal. Chem. 1968, 51(5), 1101-7; Chem. Abs. 69, 75861
(1968).
103. "Analysis of Mixed Drugs by Mass Spectrometry. X. Pesticide Analysis.
2. Analysis of Pesticides in Commercial Preparations", A. Tatematsu,
et al., Shitsuryo Bunseki 1968, 16(1), 23-9; Chem. Abs. 69_, 75861
(1968).
104. "Cleanup Procedure for Water, Soil, Animal, and Plant Extracts for
the Use of Electron-capture Detector in the Gas Chromatographic
Analysis of Organophosphorus Insecticide Residues", A. M. Kadoum,
Bull. Environ. Contam. Toxicol. 1968, 3(4), 247-53; Chem. Abs. 69,
75654 (1968).
105. "The Effect of the Column Support Material on the Gas-chromatographic
Resolution of Methyl Parathion, Ethyl Parathion, Ethyl Para-oxon,
Malathion, and Malaoxon", A. Bevenue, et al., J. Chromatogr. 1968,
35(1), 17-23; Chem. Abs. £9, 18238 (1968).
106. "Thin-layer Chromatographic-enzymic Detection of Organophosphorus
Insecticides. Activation of Weak Esterase Inhibitors", H. Ackermann
(Deut. Akad. Wiss. Berlin, Berlin, Ger.)» J« Chromatogr. 1968,
36(3), 309-17 (Ger); Chem. Abs. 69, 105284 (1968).
107. "Polyamide Layer Chromatography of Organophosphorus Pesticides",
J. T. Huang, et al., J. Pharm. Sci. 1968, 57(9), 1620-1; Chem. Abs.
.69, 85640 (1968).
108. "Detection of Thio- and Dithiophosphoric Esters and Esteraae
Inhibitor on Thin-layer Chromatograms", H. Beitz, et al., Z. Chem.
1968, 8(10), 387-8; Chem. Abs. 70, 10613 (1968).
'168
-------
1968
109. "Determination of Parathion and Methylparathion In Food", I. Camoni,
et al., Boll. Lab. Chim. Prov. 1968, 19(5), 615-29; Chem. Abs. 70,
95479 (1968).
110. "Microdetermination of Parathions by Thermo- and Ultraviolet
Decomposition Products", Y. Doi, et al., Acta Med. Okayama 1968,
22(5), 281-91; Chem. Abs. 7±, 59976 (1968).
111. "Determination of Insecticide Residue in Animal and Plant Tissues.
V. A Device to Increase the Sensitivity of the Gas Chromatography
Detector to Organophosphorus Insecticides", T. Sato, et al., Bochu
Kagaku 1968, 33(1), 8-12; Chem. Abs. 69, 9880 (1968).
112. "Qualitative Analysis of Synthetic Organic Pesticides by Spot
Tests", M. Kanda, et al., Nippon Hoigaku Zasshi 1968, 22(3), 229-51;
Chem. Abs. 72_, 65727 (1968).
113. "Detection of Pesticides by Reversed Phase Paper Chromatography",
R. T. Wang, et al., Chung Kuo Nung Yeh Hua Hsueh Hui Chih 1968,
6(3-4), 63-8; Chem. Abs. 71, 111799c (1968).
1969
114. "Column Esterification in the Gas Chromatography of the Dealkyl
Metabolites of Methyl Parathion and Methyl Paraoxon", P. S. Jaglan,
et al., Anal. Chem. 1969, 41(12), 1671-3; Chem. Abs. 21» 111792v
(1969).
115. "Pesticide Residues. Recovery of 65 Organophosphorus Pesticides
from Florisil with a New Solvent-elution System", H. Beckman, et
al., J. Ass. Offie. Anal. Chem. 1969, 52(2), 286-93; Chem. Abs.
^70, 86529 (1969).
116. "Gas Chromatography of Organophosphorus Pesticides: Retention
Times and Response Data on Three Columns", R. R. Watts, et al.,
J. Ass. Offie. Anal. Chem. 1969, 52(3), 513-21; Chem. Abs. 71,
12014 (1969).
117. "Alkaline Precolumn for Use in Gas-chromatographic Pesticide
Residue Analysis", G. A. Miller, et al., J. Ass. Offic. Anal.
Chem. 1969, 52(3), 548-53; Chem. Abs. 7±t 12014 (1969).
118. "Collaborative Study of Confirmative Procedures by Single-Sweep
Oscillographlc Polarography for the Determination of Organophosphorus
Pesticide Residues in Nonfatty Foods", R. J. Gajan, J. Ass. Offic.
Anal. Chem. 1969, 52(4), 811-17; Chem. Abs. 71, 79816 (1969).
169
-------
1969
119. "Polyamide-layer Chromatography of Organophosphorus Pesticides",
K. Nagasawa, et al., J. Chromatogr. 1969, 39(3), 282-90; Chem.
Abs. 70, 114093 (1969).
120. "Identification of Organophosphate Pesticides by Gas Chromatography
with the Flame Photometric Detector", C. W. Stanley, et al., J.
Chromatogr. 1969, 40(2), 289-93; Chem. Abs. J70, 114094 (1969).
121. "Simple and Rapid Separation of Pesticides by Polyamide
Chromatography", R. T. Wang, et al., J. Chromatogr. 1969, 42(3),
416-18; Chem. Abs. _7J.» 59977 (19*9).
122. "Gas-liquid Chromatography of Pesticides on OV-17 Stationary Phase",
V. Leoni, et al., J. Chromatogr. 1969, 43(3), 388-91; Chem. Abs. 71,
116426 (1969).
123. "Thin-layer Chromatographic-enzymic Detection of Organophosphorus
Insecticides. Thin-layer Chromatographic Behavior of Some Other
Insecticides", H. Ackermann, J. Chromatogr. 1969, 44(2), 414-18;
Chem. Abs. 72., 77909 (1969).
124. "Field lonization Spectra of Some Pesticidal and Other Biologically
Significant Compounds", J. N. Damico, et al., Int. J. Mass Spectrom.
Ion Phys. 1969, 2(2), 161-82; Chem. Abs. .70, 105781 (1969).
125. "Determination of Organophosphorus Pesticides in Water", G. Zweig,
et al., Residue Rev. 1969, 26, 17-36; Chem. Abs. 71, 80100 (1969).
126. "Gas Chromatography of Methyl Parathion and Its Principal Alteration
Products with Demonstration of Use in Selected Chemical and Bio-
chemical Problems", P. S. Jaglan, 1969, 218 pp., Univ. of Calif.
(Riverside) Dissertation; Chem. Abs. 74, 3025 (1969).
127. "Chromatographic Determination of Trace Amounts of Pesticide
Residues", M. Beroza, et al., Trace Subst. Environ. Health-3, Proc.
Univ. Mo. Annu. Conf., 3rd 1969, 331-51; Chem. Abs. 74, 2973 (1969).
128. "Pesticide Residues. XIX. Determining Pesticide Residues In
Natural Waters. 1. General Analytical Methods", R. Mestres, et
al., Ann. Fals. Expert. Chim. 1969, 62(685), 75-85; Chem. Abs. 73,
34095 (1969).
129. "Analysis of Chlorinated and Organic Phosphorus Pesticides by Gas
Chromatography", M. Kanda, et al., Nippon Haigaku Zasshi 1969, 23(6),
477-86; Chem. Abs. _73, 65310 (1969).
130. "Experience in Improving the Sanitary Working Conditions in the
Production of Organophosphorus Toxic Chemicals", V. N. Trefilov,
et al., Kazan. Med. Zh. 1969, (1), 76-8; Chem. Abs. 74, 90845 (1969).
170
-------
1969
131. "Hematological Shifts in Workers Engaged in the Production of
Organophosphorus Toxic Chemicals", I. S. Faerman, et al., Ter.
Arkh. 1969, 41(12), 23-8; Chem. Abs. .72, 70368 C1969).
132. "Simple and Rapid Reversed Phase Thin-layer Chromatography of
Pesticides", R. T. Wang, et al., Hua Hsueh 1969, (4), 80-5; Chem.
Abs. J74, 2945 (1969).
1970
133. "Microcolumn Chromatographic Cleanup for the Analysis of
Pesticides in Water", L. M. Law, J. Ass. Of fie. Anal. Chem. 1970,
53(6), 1276-86; Chem. Abs. 2i» 2945 (1970).
134. "Gas-liquid Chromatographic Determination of Methyl Parathion and
Metabolites", P. S. Jaglan, et al., J. Agr. Food Chem. 1970, 18(5),
809-13; Chem. Abs. .73, 97742 (1970).
135. "Effect of Temperature and Ultraviolet Radiation on the Persistence
of Methyl Parathion and DDT in Soils", R. D. Baker, et al., Agron.
J. 1970, 62(4), 509-12; Chem. Abs. J73, 65337 (1970).
136. "Correlations Between Phosphorus-31 NMR Chemical Shifts and
Structures of Some Organophosphorus Pesticides", R. T. Ross, et al.,
Anal. Chlm. Acta 1970, 52(1), 139-41; Chem. Abs, 2i» 31012 (1970).
137. "Report on Phosphated Pesticides", K. A. McCully, J. Ass. Offie.
Anal. Chem. 1970, 53(2), 363-5; Chem. Abs. 72, 131134 (1970).
138. "GLC (Gas-liquid Chromatographic) Retention Times of Pesticides
and Metabolites Containing Phosphorus and Sulfur on Four Thermally
Stable Columns", M. C. Bowman, et al., J. Ass. Offic. Anal* Chem.
1970, 53(3), 499-508; Chem. Abs. j[3, 24175 (1970).
139. "Comparison of Several Liquid Phases in Gas Liquid Chromatography
of Methyl Parathion and Metabolites", P. S. Jaglan, et al., Bull.
Environ. Contain. Toxicol. 1970, 5(2), 98-103; Chem. Abs. 73, 95225
(1970).
140. "Single Column Gas-liquid Chromatography of Methyl Parathion and
Metabolites Using Temperature Programming", P. S. Jaglan, et al.,
Bull. Environ. Contam. Toxicol. 1970, 5(2), 111-14; Chem. Abs. 73,
95225 (1970).
141. "Phosphorimetric Determination of Some Pesticides Derived from
p-nitrophenol", E. A. Martin, Can. J. Pharm. Sci. 1970, 5(1),
13-15; Chem. Abs. 73, 24174 (1970).
171
-------
1970
142. "Gas Chromatographic Behavior and Chemical Structure of Methyl
Parathion and Methyl Paraoxon in Relation to Their Homologs",
P. S. Jaglan, et al., J. Chromatogr. 1970, 46(1), 79-84; Chem.
Abs. 72, 77831 (1970).
143. "Effect of Ultraviolet Irradiation on the Thin-layer Chromatography
of Insecticidal Phosphates and on Their Detection by the Benzo-
hydroxamic Acid Reaction", W. Ebing, J. Chromatogr. 1970, 46(2),
180-6; Chem. Abs. 7j2, 89171 (1970).
144. "Gas Chromatographic Analysis of Organophosphorus Pesticides",
D. B. Girenko, et al., Gig. Sanit. 1970, 35(5), 77-9; Chem. Abs.
_73, 65310 (1970).
145. "Spray Method for the Fluorescent Detection of Sulfur-containing
Organic Compounds", P. E. Belliveau, et al., J. Chromatogr. 1970,
48(3), 478-83; Chem. Abs. T3* 65310 (1970).
146. "Detection, Separation, and Quantitative Recovery of Thirteen
Organophosphorus Pesticides on Silica Gel GF_5, Thin-layer Chromato-
grams", D. C. Villeneuve, et al., J. Chromatogr. 1970, 48(3),
567-71; Chem. Abs. 73, 54905 (1970).
147. "Effect of Liquid Phase Loading and Temperature on the Relative
Retentions in the Gas Chromatography of Methyl Parathion and
Parathion", P. S. Jaglan, et al., J. Chromatogr. 1970, 50(3),
520-2; Chem. Abs. T3* 108636 (1970).
148. "Design of a Polarographic Detector for High Speed, High Efficiency
Liquid Chromatography in Columns and Its Evaluation for the
Quantitative Analysis of Pesticides", J. G. Koen, et al., J.
Chromatogr. Sci. 1970, 8 (April), 192-9; Chem. Abs. .73, 13438 (1970),
149. "Comparison of Determination of Hydrolysis Rates of Methyl Parathion
and Methyl Paraoxon by Gas Liquid Chromatography and Spectrometry",
P. S. Jaglan, et al., J. Chromatogr. Scl. 1970, 8(8), 483-5; Chem.
Abs. 21, 87187 (1970).
150. "Application of Combined Differential Scanning Calorimetry-mass
Spectrometry (DSC-MS) to the Study of Thermal and Oxidative
Decompositions", G. Dugan, et al., Anal. Calorimetry, Proc. Symp.,
2nd 1970, 417-27; Chem. Abs. 74, 150927 (1970).
151. "Determination of Organophosphorus Insecticides in the Air", E.
Arato Sugar, et al., Munkavedelem 1970, 16(1-3), 50-4; Chem. Abs.
73, 90938 (1970).
152. "Determination of Organophosphorus Compounds by Paper Chromatography
According to the Fluorescence Capacity in Ultraviolet Light", R. V.
Mishina, Metody Anal. Pestits. 1970, 67-71 (Russ); Chem. Abs. 76.
42547 (1970).
172
-------
1970
153. "0,0-Dimethyl O-(Substituted-phenyl) Thiophosphates", R. Schelle,
et al., Ger. (East) 70,871, 20 Jan 1970; Chem. Abs. 73, 76847 (1970).
1971
154. "Removal of Sulfur in Environmental Samples Prior to Gas Chromato-
graphic Analysis for Pesticide Residues", R. L. Schutzmann, et al.,
J. Ass. Offic. Anal. Chem. 1971, 54(5), 1117-19; Chem. Abs. 2i»
757 (1971).
155. "Negative Ion Mass Spectra of Some Pesticidal Compounds", P. C.
Rankin, J. Ass. Offic. Anal. Chem. 1971, 54(6), 1340-8; Chem. Abs.
26, 69024 (1971).
156. "Method for Confirmation of Organophosphorus Compounds at the
Residue Level", M. T. Shafik, et al., Bull. Environ. Contarn.
Toxicol. 1971, 6(1), 55-66; Chem. Abs. 74, 124007 (1971).
157. "Rate of Hydrolysis of Seven Organophosphate Pesticides", R. P.
Cowart, et al., Bull. Environ. Contam. Toxicol. 1971, 6(3), 231-4;
Chem. Abs. 25, 97570 (1971).
158. "Routine Method for the Determination of Organophosphorus Insecti-
cides by Thin-layer Chromatography", 0. Antoine, et al., J. Chromatogr.
1971, 58(2), 247-56; Chem. Abs. 75., 75226 (1971).
159. "Separation of Fifty Pesticides and Related Compounds and Poly-
chlorobiphenyls into Four Groups by Silica Gel", V. Leoni, J.
Chromatogr. 1971, 62(1), 63-71; Chem. Abs. 2i» 82030 (1971).
160. "Extractive Spectrophotometric Methods for the Detection and
Determination of p-nitrophenol in Urine in 'Wofatox* Poisoning",
E. Sallay, et al., Orv. Hetil. 1971, 112(12), 677-8; Chem. Abs.
25, 4454 (1971).
161. "Thin-layer Chromatographic Analysis of Organophosphate Pesticides
in the Study of Environmental Contamination (Italian Surface Waters)",
V. Leoni, et al., Farmaco, Ed. Prat. 1971, 26(7), 383-93; Chem. Abs.
75, 128754 (1971).
162. "Analytical Studies on Pesticides and Related Compounds. VI.
Colorimetric Determination of S-benzyl 0-butyl, S-ethyl Phosphoro-
dithioate and Some Other Organophosphorus Pesticides", A. Murano,
et al., Bunseki Kagaku 1971, 20(6), 665-72; Chem. Abs. 75, 97518
(1971).
173
-------
1971
163. "Assay of Methyl Parathion and Fenitrothion in Crop Extracts Using
Vapor-phase Separation in Conjunction with Gas Chromatography",
M. S. Khan, et al., Pak. J. Sci. Ind. Res. 1971, 14(4-5), 360-3;
Chem. Abs. TT_, 46776 (1971).
164. "Contamination of Working Clothes and Tegumens of Workers Engaged
in the Production of Metaphos and Chlorophos", V. N. Trefilov, et
al., Gig. Tr. Prof. Zabol. 1971, 15(2), 51-3; Chem. Abs. 74_, 102765
(1971).
165. "Esterase Inhibition Technique for the Detection of Organophosphorus
Pesticides on Thin-layer Chromatograms", T. Stijve, et al., Mitt.
Geb. Lebensmittelunters. Hyg. 1971, 62(1), 25-31; Chem. Abs. 75.
117188 (1971).
166. "0,0-Dialkyl 0-phenyl Phosphorothioates", Velsicol Chemical Corp.,
U.S. 3,590,104, 29 Jun 1971; Chem. Abs. 75_, 63387 (1971).
167. "Catalytically Preparing Phosphate Esters", Kerr-McGee Corp., U.S.
3,607,991, 21 Sep 1971; Chem. Abs. 75, 129519 (1971).
168. "Steam Distillation of Thermally Unstable Substances", W. Steinke,
et al., Ger. (East) 82,904, 5 Jul 1971; Chem. Abs. 77, 37041 (1971).
1972
169. "Elution Solvent System for Florisil Column Cleanup in Organochlorine
Pesticide Residue Analyses", P. A. Mills, et al., J. Ass. Offic.
Anal. Chem. 1972, 55(1), 39-43; Chem. Abs. 76, 71129 (1972).
170. "Infrared Analysis of Pesticide Formulations", S. W. Goza, J. Ass.
Off. Anal. Chem. 1972, 55(5), 913-17; Chem. Abs. Tl_% 160891 (1972).
171. "Rapid Liquid Chromatography on Aluminum Oxide", D. Randau, et al.,
J. Chromatogr. 1972, 66(2), 382-5; Chem. Abs. 7_7, 31066 (1972).
172. "Alkyl Phenyl Phosphates and Phosphoro(di)thioates", Stauffer
Chemical Co., Ger. Offen. 2,162,344, 13 Jul 1972; Chem. Abs. 77,
114033 (1972).
174
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MONURON
1952
(1) "Determination of Macro and Micro Quantities of 3-(p-chlorophenyl)-
1,1-dimethylurea", W. K. Lowen, et al., Anal. Chem. 24, 1475-9
(1952); Chem. Abs. 46, 11042a (1952).
1953
(2) "Microdetermination of 3-(p-chlorophenyl)-1,1-dimethylurea in
Plant Tissue", H. Y. Young, et al., Anal. Chem. 25, 800-2 (1953);
Chem. Abs. 47, 8587g (1953).
(3) "l-Aryl-3-alkylureas", E. I. Du Pont de Nemours & Co., U.S.
2,655,534, Oct. 13, 1953; Chem. Abs. 48, 11490 (1954).
1954
(4) "Determination of 3-(p-chlorophenyl)-l,l-dimethylurea in Soils
and Plant Tissue", W. E. Bleidner, et al., J. Agr. Food Chem.
1, 476-9 (1954); Chem. Abs. 48, 7837 (1954).
(5) "Application of Chromatography for Determining Microquantities
of 3-(p-chlorophenyl)-1,1-dimethylurea", W. E. Bleidner, et al.,
J. Agr. Food Chem. 2, 682-4 (1954); Chem. Abs. 48, 13544c (1954).
(6) "Chlorophenyldimethylureas", E. I. du Pont de Nemours & Co., U.S.
2,673,877, March 30, 1954; Chem. Abs. 49, 4018b (1955).
1955
(7) "Synthesis of N-p-chlorophenyl-N1,N'-dimethylurea", Fan-Tih
Chiang, J. Chinese Chem. Soc., Ser. II, 2, 129-31 (1955); Chem.
Abs. 50, 16691f (1956).
(8) "l-(p-Chlorophenyl)-3,3-dimethylurea", Toyama Chemical Industries
Co., Japan 2976, Apr. 30, 1955; Chem. Abs. 51, I6534a (1957).
1956
(9) "Substituted Ureas", Allied Chemical & Dye Corp. U.S. 2,729,677,
Jan. 3, 1956; Chem. Abs. .51, 470b (1957).
(10) "Alkyl Aryl Ureas", Imperial Chemical Industries Ltd. U.S.
2,768,971, Oct. 30, 1956; Chem. Abs. 51, 74llc (1957).
175
-------
1957
(11) "Substituted Urea Herbicides", A. L. Abel, Chem. & Ind. (London)
1957. No. 33, 1106-12; Chem. Abs. 51, 18437f (1957).
1958
(12) "Separation and Identification of Chlorinated Organic Pesticides
by Paper Chromatography. XI. A Study of 114 Pesticide Chemicals:
Technical Grades Produced in 1957 and Reference Standards",
L. C. Mitchell, J. Assoc. Offic. Agr. Chemists 41, 781-816
(1958); Chem. Abs. 53, 2525b (1959).
1959
(13) "Substituted Urea Compounds", Badische Anilin-Soda-Fabrik
Akt.-Ges. Ger. 1,064,051, Aug. 27, 1959; Chem. Abs. 55, 13373b
(1961).
(14) "Substituted Ureas", E. I. du Pont de Nemours & Co. Brit. 811,681,
Apr. 8, 1959; Chem. Abs. 53, 18872i (1959).
1961
(15) "The Effect of Ultraviolet Light (2537 A.) on 141 Pesticide
Chemicals by Paper Chromatography", L. C. Mitchell, J. Assoc.
Offic. Agr. Chemists 44, 643-712 (1961); Chem. Abs. 56, 3849e
(1962).
(16) "Photochemical Degradation of Diuron and Monuron", L. W. Weldon,
Weeds .9(1), 111-16 (1961); Chem. Abs. 61, 3629c (1964).
1962
(17) "Trace Analysis by Programmed-Temperature Gas Chromatography--r
Simultaneous Determination of Monuron and Diuron Herbicide
Residues", J. J. Kirkland, Anal. Chem. 34, 428-33 (1962); Chem.
Abs. 56, 14664b (1962).
(18) "Investigations in the Use of the Microcoulometric Gas Chromato-
hraph for Pesticide Residue Analysis", J. Burke, et al., J. Assoc.
Offic. Agr. Chemists 45, 348-54 (1962); Chem. Abs. 57, 2626g
(1962).
(19) "Determination of Residues of Diuron, Monuron, Fenuron, and
Neburon", R. L. Dalton, et al., J. Assoc. Agr. Chemists 45. 377-81
(1962); Chem. Abs. .57, 2638h (1962).
176
-------
(20) A New Synthesis of Ureas. IV. The preparation of Unsynmetrical
Ureas from Carbon Monoxide, Sulfur, and Amines", R. A. Franz,
et al., J. Org. Chem. 27, 4341-6 (1962); Chem. Abs. 58, 5546f
(1963).
(21) "Herbicides and Plant Growth Regulators. XXXVIII. A New Method
of Preparation of Aryldialkylureas", N. N. Mel'nikov, et al.,
Zh. Obshch. Khim. 32, 3957-9 (1962); Chem. Abs. 58, 11245f (1963).
(22) "The Promising Utility of Infrared Assay of Pesticides and Their
Residues. II. R. C. Blinn, et al., Pesticide Res. Bull. 2(4),
3-11 (1962); Chem. Abs. 60, 13811g (1964).
(23) "Separation and Colorimetrie Determination of Monuron and
Diuron Residue", H. I. Pease, J. Agr. Food Chem. 10, 279-81
(1962); Chem. Abs. 6,1, 15257h (1964).
(24) "Photodecomposition of Herbicides", L. S. Jordan, et al., Res.
Progr. Rept. Western Weed Control Conf. 1962. 89-90; Chem. Abs.
63, 13960a (1965).
1963
(25) "Effect of Sunlight on Absorption Spectra of Substituted Urea and
Triazine Herbicides", L. S. Jordan, et al., Res. Progr. Rept.
Western Weed Control Conf. 1963. 78-9; Chem. Abs. 63, 13959b
(1965).
(26) "Effect of Ultraviolet Light on Substituted Urea and Triazine
Compounds", L. S. Jordan, et al., Res. Progr. Rept. Western Weed
Control Conf. 1963. 79; Chem. Abs. 63, 13959d (1965).
(27) "Photodecomposition of Monuron on the Soil Surface", L. S. Jordan,
et al., Res. Progr. Rept. Western Weed Control Conf. 1963. 80;
Chem. Abs. 63, 13959h (1965).
1964
(28) "Photodecomposition of Substituted Phenylureas", L. S. Jordan,
et al., Weeds .12(1), 1-4 (1964); Chem. Abs. 60, H302e (1964).
(29) "Thin-Layer Chromatographic Behavior of Compounds Effective as
Herbicides", H. G. Henkel, Chimia (Aarau) .18(7), 252-4 (1964);
Chem. Abs. £1, 8828d (1964).
(30) "Monuron Diuron and Neburon", W. K. Lowen, et al., Ibid. 157-70,
Anal. Methods Pesticides, Plant Growth Regulators, Food Additives
(Gunter Zweig, editor, Academic 4, (1964); Chem. Abs. 62, 58l9h
(1965). ~ ~
177
-------
1965
(31) "Effects of Ultraviolet Light on Herbicides", L. S. Jordan,
et al., Weeds 13(1), 43-6 (1965); Chem. Abs. 62, 8330b (1965).
(32) "Gas Chromatography of Trimethylsilyl Derivatives.. I. Pesti-
cidal Carbamates and Ureas", L. Fishbein, et al., J. Chromatog.
20(1), 9-14 (1965); Chem. Abs. 64, 4193d (1966).
1966
(33) "Direct Gas Chromatographic Determination of Herbicidal N-
phenylurea Derivatives", H. G. Henkel, J. Chromatog. 21(2).
307-11 (1966); Chem. Abs. 64, 11783a (1966).
(34) "N-p-Chlorophenyl-N',N'-dimethylurea", U.S.S.R. 178,367,
Jan. 22, 1966; Chem. Abs. 64, 19487b (1966).
(35) "Determination of the Substituted Urea Herbicides Linuron,
Monuron, Diuron, Neburon, and Fenuron in Surface Waters",
E. Katz, J. Assoc. Offie. Anal. Chemists 49(2), 452-6 (1966);
Chem. Abs. 65, 1958c (1966).
(36) "Gas Chromatographic Column for Pesticide Residue Analysis;
Retention Times and Response Data", J. A. Burke, et al., J.
Assoc. Offic. Anal. Chemists 49(2), 374-85 (1966); Chem. Abs.
65, 2894g (1966).
(37) "Determination of Residual Concentration of 3-(p-chlorophenyl)-
1,1-dimethylurea in Reservoir Waters After Their Treatment With
Monuron", A. D. Konenko, et al., Gidrobiol Zh., Akad. Nauk Ukr.
SSR1(2), 65-7 (1966); Chem. Abs. 65, 5217c (1966).
(38) "Separation and Identification of Substituted Urea Herbicides",
by paper Chromatography. L. C. Mitchell, J. Assoc. Offic. Anal.
Chem. 49(6), 1163-6 (1966); Chem. Abs. 66, 45679g (1967).
(39) "Occupation Hygiene and Health Status of Workers Engaged in the
Production of Monuron", M. M. Levina, et al., Gig. Tr. Prof.
Zabol. 10(11), 54-6 (1966); Chem. Abs. 66, 68679w (1967).
(40) "Sulfonylarylurea*Compounds", Farbwerke Hoechst A.-G. Neth.
Appl. 6,605,709, Nov. 4, 1966; Chem. Abs. 66, 85603j (1967).
(41) "Photocolorimetric Determination of Monuron Herbicide in Plant
Tissues", E. M. Kazarina, et al., Metody Opred. Regul. Rosta
Gerbits., Akad. Nauk SSSR, Inst. Fiziol. Rast. 1966. 149-55;
Chem. Abs. 67, 42619x (1967).
178
-------
(42) "Influence of Structural Characteristics on Inhibition of the Hill
Reaction", A. Alcaide, et al., An. Real. Soc. Espan. Pis. Quim.,
Ser B 62 (12), 1391-1402 (1966); Chem. Abs. £7, 90479y (1967).
1943
(43) "Specific Detection of Urea Herbicide Residues by Separation of
Their Amines on Cellulose Thin-Layer Plates", H. Geissbuchler,
et al., J. Chromatogr. 27(1), 296-9 (1967); Chem. Abs. 67, 10438w
(1967).
1967
(44), "Thin-Layer Chromatography of Some Carbamate and Phenylurea Pesti-
cides", J. M. Finocchiaro, et al., J. Assoc. Offic. Anal. Chem.
50(4), 888-96 (1967); Chem. Abs. 67, 81415x (1967).
(45) "Thin-Layer Chromatographic Separation, Identification, and Estima-
tion of Residues of Some Carbamate and Allied Pesticides in Soil
and Water", D. C. Abbott, et al., J. Chromatogr. 30(1), 136-42
(1967); Chem. Abs. J67, 11605le (1967).
(46) "Preparation of N'-aryl-N, N-dimethylureas", U.S.S.R. 193,492,
March 13, 1967, From Izobret., Prom Obratxy, Tovarnye Znaki 1967.
44(7), 33; Chem. Abs. 69, 18638y (1968).
(47) "N-Arul-N1, N'-diaIkylureas", Romania Ministry of the Chemical
Indus-try, Rom. 48,811, September 5, 1967; Chem. Abs. 69.
35682a (1968).
(48) "Determination of Simazine and Monuron in Soil, Citrus Fruits,
Grape Juice, and Tea Leaves", A. A. Gigineishvili, Mater. Sess.
Zakavkaz. Sov. Koord. Nauch.-Issled. Rab. Zashch. Rast. 1967.
555-6; Chem. Abs. 73, 119443u (1970).
1968
(49) "A High-Performance Ultraviolet Photometric Detector for Use
With Efficient Liquid Chromatographic Columns", J. J. Kirkland,
Anal. Chem. 40(2), 391-6 (1968); Chem. Abs. £8, 56400b (1968).
(50) "Thin-Layer Chromatography; Relative Migration Data [R^gl of
Chlorinated Pesticides", E. J. Thomas, et al., J. Chromatogr.
1968. 35(1), 119-21; Chem. Abs. ,69, 18229r (1968).
(51) "Determination of Small Quantities of Monuron in Water, Algae,
and Soil By Thin-Layer Chromatography", L. S. Samosvat, Gidrobiol.
Zh. Akad. Nauk Ukr. SSR 1968. 4(4), 78-81; Chem. Abs. 69, 103655w
(1968).
179
-------
1968
(52) "Use of Hydriodic Acid In the Detection of Pesticides After Thin-Layer
Chromatography", Askew, J., et al., J. Chromatogr. 1968. 37(2), 369-72,
Chem. Abs. 22, 10572x (1969).
(53) "Versatility of OV-17 Substrate For Gas Chromatography of Pesticides",
C.A. Bache, et al., J. Assoc. Offie. Anal. Chem. 1968. 51(6), 1270-1
(Eng), Chem. Abs. 70, 27907h (1969).
(54) "Determination of Residual Quantities of Herbicides in Foods By Thin-
Layer Chromatography" L. S. Samosvat, Khim. Sel. Khoz. 1968. 6(10),
769-70, Chem. Abs. 70, 56356h (1969).
1969
(55) "Pesticide Residues. Indoxyl Acetate Spray Reagent for Flurogenic
Detection of Cholinesterase Inhibitors in Environmental Samples",
R. L. Schutzmann, et al., (Plant Pest Contr. Div., Agr. Res.
Serv., Gulport, Miss.). J. Ass. Offie. Anal. Chem. 1969. 52(1)
151-6, (Eng), Chem. Abs. 70> 56345d (1969).
(56) "Bratton-Marshall Reagent for the Detection of Substituted Urea
Herbicide^ and Metabolites on TLC (Thin-Layer Chromatography)
Plates", J. H. Onley, et al., J. Ass. Offic. Anal. Chem. 1969.
52(3), 545-7. Chew. Abs. 71, 11797g (1969).
(57) "Analysis of a Single Crop Extract for Substituted Urea Herbicides
and Metabolites, Chlorinated Insecticides,and Amitrole" J. H. Onley,
et al., J. Ass. Offic. Anal. Chem. 1969. 52(3), 526-32 (Eng),
Chem. Abs. 71, 21125a (1969).
(58) "Use of Thin-Layer Chromatography for Determination of Herbidide
Residues in Biological Material", L. S. Samosvat, Gig. Sanit.
1969. 34(4), 77-9 (Russ.), Chem. Abs. 2I» 37637e (1969).
(59) "Determination of Low Levels of Monuron in Air", KH. YA. Vengerskaya,
et al., Med. Zh. Uzb. .1969, (3), 65-6, Chem. Abs. jfl, 638l6g (1969).
(60) "Photodecompnsition o* 3-(p-chloropbenyl)-l,l-dimethylurea
(monuron)", D. G. Crosby, et al., J. Agr. Food Chem. 1969.
17(5), 1041-4, Chem. Abs. 21. 100717y (1969).
(61) "Synthesis of Urea Derivatives and a Study of Them by Anodic
Polarography", I. B. Romanova, et al., Zh. Obshch. Khim. 1969.
39(9), 1921-4, Chem. Abs. 72, 3l403z (1970).
180
-------
(62) "Chromatncraphic Identification of Substituted Urea Herbicides",
R. J. Hance, J. Chromatogr, 1969. 44(2), 419-21 (Eng), Chem.
Abs. 22, 41984d (1970).
1970
(63) "Phosphorimetrie Determination of Some Chlorinated Pesticides",
E. A. Martin, Can. J. Pharm. Sci. 1970. 5(2), 52-5(Fr), Chem.
Abs. 73, 7b020j (1970).
(64) "Chromogenic Agent for Detecting Dimethylurea Herbicides on Thin-
Layer Chromatographic Plates", M. Look, et al., J. Chromatogr,
1970. 50(1), 145 (Eng), Chem. Abs. 73, 97632a (1970).
(65) "Infrared Band Assignment of Some Substituted Urea Compounds",
J. T. Kim, Daehan Hwahak Hwoejee 1970. 14(2), 147-53, Chem.
Abs. 74, 26378g (1971).
(66) "Systematic Identification and Determination of Pesticides. 2.
Lower Limits of Detection of Pesticides on Thin Layer Plates",
K. Suzuki, et al., Noyaku Kensasho Hokoku 1970. No. 10, 24-31,
Chem. Abs. 75, 446Ix (1971).
1971
(67) "Amperometric Determination of Pesticides in Technical Products and
Formulations", G. Kynas't, Fresenius Z. Anal. Chem. 1971. 255(3),
201-5, Chem. Abs. 76, 10934r (1972).
(68) "Infrared and Ultraviolet Spectra of Seventy-Six Pesticides",
R. C. Gore, et al., J. Ass. Offic. Anal. Chem. 1971. 54(5), 1040-82,
Chem. Abs. 75, 117202g (1971).
(69) "Electrolytic Conductivity Detection of Some Nitrogen-Containing
Herbicides", W. P. Cochrane, et al., J. Chromatogr 1971. 63(2),
364-9 (Eng), Chem. Abs. T±, 122725e (1972).
1972
(70) "Routine Method for Identification of Pesticide Residues",
W. Ebing, J. Chromatogr, 1972. 65(3), 533-45, Chem. Abs.
2Z, 1626k (1972).
(71) "Photolysis of 3-(p-chlorophenyl)-l, 1-dimethylurea (monuron)
and 3-phenyl-l, 1-dimethylurea (fenuron)", P. H. Mazzocchi,
et al., J. Agr. Food Chem. 1972. 20(5), 957-9 (Eng), Chem.
Abs. 77, 139184w (1972).
181
-------
(72) "Phenylamide Pesticides in Natural Waters". M. A. El-Dib, et al.,
J. Ass. Off. Anal. Chem. 1972. 55(6), 1276-9, Chem. Abs. 7B,
2509Id (1973).
(73) "Use of a gas-chromatographi^Method for Analyzing Residual Amounts
of Phenyl-Substituted Urea Derivatives", D. B. Girenko, et al.,
Vop. Pitan. 1972. 31(5), 89-91, Chem. Abs. 781 2799UV (1973).
(74) "Potentiometric Determination of Monuron in Herbicide Formulations",
S H Yuen, et al., Analyst (London) 1972. 97(1160), 921-2, Chem.
Abs. _/8, J9091r (1973).
(75) "Determination of Some Pesticides in Environmental Materials by
Gas-Liquid Chromatography", D. G. Gireako, et al., Probl. Anal.
Khim. 1972. 2, 39-43 (Russ), Chem. Abs. 22» 62444n (1973).
(76) "Determination of Organochlorine Insecticides", F. G. Dyatlovitiskaya,
et al., Probl. Anal. Khim. 1972. 2, 43-6 (Russ), Chem. Abs. 79,
62445p (1973).
1973
(77) "Dialkylammonium Dialkylthiolcarbamates", Quimco G. m. b. H. Ger.
Offen. 2.258.453. 14 Jun 1973, Chem. Abs. 79, 52829c (1973).
(78) "Determination of Monuron, Diuron, and Fenuron by Anodic Volt*
Amperometry", U. S. Kulukova, et al., Khim. Sel. Khoz. 1973.
11(4), 296-8, Chem. Abs. 79, 74735w (1973).
182
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PARATHION
1948
(1) "Preparation of 0,0-Diethyl 0-p-Nitrophenyl Thiophosphate (Parathion)",
J. H. Fletcher et al., J. Am. Chem. Soc. 70, 3943-4 (1948); Chem.
Abs. 43, 13131 (1949).
(2) "Estimation of Small Amounts of 0,0-Diethyl O-(p-Nitrophenyl) Thio-
phosphate", P. R. Averell et al., Anal. Chem. 20, 753-6 (1948);
Chem. Abs. .42, 8714g (1948).
1949
(3) "Chemistry of Phosphoric Esters", J. Henriet, Parasitica (Gembloux)
5, 54-67 (1949); Chem. Abs. 44, 5247b (1950).
(4) "Source of Error in Estimating Small Amounts of Parathion", F. I.
Edwards, Jr., Anal. Chem. 21, 1415-16 (1949); Chem. Abs. 44, 3201h
(1950).
(5) "p-Nitrophenyl Diethyl Thiophosphate11, Victor Chemical Works, U. S.
2,471,464, May 31, 1949; Chem. Abs. 43, 66591 (1949).
1950
(6) "Synthesis of Parathion and Some Closely Related Compounds", J. H.
Fletcher et al., J. Am. Chem. Soc. 72, 2461-4 (1950); Chem. Abs.
44, 9933b (1950).
(7) "Use of Amine and Phosphine Catalysts in the Preparation of Parathion",
A. D. F. Toy et al., J. Am. Chem. Soc. 72, 3191-2 (1950); Chem. Abs.
44, 10673d (1950).
(8) "Analysis of p-Nitrophenyl Diethyl Thiophosphate, E 605, Parathion",
J. C. Gage, Analyst 75, 189-91 (1950); Chem. Abs. 44, 7013h (1950).
(9) "Synthesis and Development of Parathion and Related Compounds", J. T.
Cassady et al., Ibid. 143-9; Chem. Abs. 44, 7009c (1950).
(10) "Organic Phosphorus Insecticides", S. A. Hall, Ibid. 150-9; Chem.
Abs. 44, 7009c (1950).
(11) "Polarographic Determination of 0,0-Diethyl 0-p-Nitrophenyl Thio-
phosphate (Parathion), C. V. Bowen et al., Advances in Chem. Ser.
No. 1, 198-201; Chem. Abs. 44, 7010c (1950).
183
-------
(12) "Report on (Determination of) Parathion", F. I. Edwards, Jr., J.
Assoc. Offie. Agr. Chemists 33, 783-7 (1950); Chem. Abs. 45, 803h
(1951).
(13) "Infrared Spectra of Organic Thiophosphates", R. C. Gore, Discussions
Faraday Soc. 1950, No. 9, 138-43; Chem. Abs. 46., 3408e (1952).
(14) "New Organic Phospho Compounds", K. Kjeldgaard, Arc. Pharm. Chemi.
57, 187-92 (1950); Chem. Abs. 44, 5309c (1950).
(15) "Newer Organic Insecticides", H. L. J. Haller, Proc. 8th Intern.
Congr. Entomol., Stockholm 1948, 916-19 (1950); Chem. Abs. 45. 8699a
(1951).
(16) "Synthesis and Insecticidal Properties of Some Esters of Phosphoric
Acid", N. N. Mel'nikov et al., Doklady Akad. Nauk. S.S.S.R. 71, 485-7
(1950); Chem. Abs. 44, 8041h (1950).
(17) "Mixed Aryl Alkyl Thiophosphates", Plant Products Corp., U. S.
2,506,344, May 2, 1950; Chem. Abs. 44, 6882a (1950).
(18) "Dialkyl Nitrophenyl Phosphates and Thiophosphates", American Cyanamid
Co., Brit. 644,616, Oct. 11, 1950; Chem. Abs. 45, 3862h (1951).
1951
(19) "Determination of Parathion in Air Samples by Ultraviolet Absorption
Spectroscopy", R. C. Hirt et al., Anal. Chem. 23, 185-7 (1951); Chem.
Abs. 45, 3983i (1951).
(20) "Report on [Determination of] Parathion", P. A. Clifford, J. Assoc.
Offie. Agr. Chemists 34, 533-6 (1951); Chem. Abs. 45, 10469c (1951).
(21) "Determination of Parathion and p-Nitrophenol in Technical Grade
Materials and in Dust Preparations", K. O'Keeffe et al., Anal. Chem.
23, 1167-9 (1951); Chem. Abs. 45, 10469d (1951).
(22) "Chemical Studies on Insecticides - Determination of Parathion and
Dimethylparathion", J. A. A. Ketelaar et al., Anal. Chem. 23, 646-50
(1951); Chem. Abs. 45, 6340c (1951).
(23) "Estimation of 0,0-Diethyl,0-p-Nitrophenyl Thiophosphate. Modified
Semimicro Method", C. W. Wilson et al., Anal. Chem. 23, 1487-9 (1951);
Chem. Abs. 46, 2742i (1952).
(24) "Parathion - Preparation, Properties, and Use", G. A. Ingham, Chemistry
in Can. 3, No. 5, 38-41 (1951); Chem. Abs. 45, 6789b (1951).
(25) "Properties of 0,0-Diethyl-O-p-Nitrophenyl Thiophosphate and 0,0-
Diethyl 0-p-Nitrophenyl Phosphate", E. F. Williams, Ind. Eng. Chem.
43, 950-4 (1951); Chem. Abs. 46, 54a (1952).
184
-------
(26) "The Analysis of Phosphate Esters. I. The Pure Material", P.
Reckendorfer, Pflanzenschutzber. 5, 287-95 (1950); Chem. Abs. 48,
112481 (1954).
(27) "Phosphoric Acid Esters", Eastman Kodak Co., U. S. 2,571,656, Oct.
16, 1971; Chem. Abs. 46, 3065h (1952).
(28) "Dialkyl p-Nitrophenyl Thionophosphates", United States Rubber Co.,
U. S. 2,575,224, Nov. 13, 1951; Chem. Abs. 46, 3566d (1952).
(29) "Dialkyl p-Nitrophenyl Thionophosphates", United States Rubber Co.,
U. S. 2,575,225, Nov. 13, 1951; Chem. Abs. 4£, 3566e (1952).
(30) "Rapid Assay of Parathion in Wettable Dusts", E. Romano et al., Ann.
Sper. Agrar. (Rome) [N.S.] 5,1527-31 (1951); Chem. Abs. 46_, 5248b
(1952).
1952
(31) "Determination of p-Nitrophenol and p-Nitrophenyl-0,S-Diethyl Thio-
phosphate in Parathion", J. C. Gage, Analyst 77, 123-6 (1952); Chem.
Abs. 46, 5247c (1952).
(32) "Report on Parathion", F. I. Edwards, Jr., J. Assoc. Offic. Agr.
Chemists 35, 381-6 (1952); Chem. Abs. 46., 11561b (1952).
(33) "Identification and Properties of the Colored Compound Formed in
Parathion Estimations", R. C. Blinn et al., J. Am. Chem. Soc. 74,
5516-18 (1952); Chem. Abs. 49_, 981g (1955).
(34) "The Infrared Spectra of Some Organophosphorus Esters", 1. L. J.
Bellamy et al., J. Chem. Soc. 475-83 (1952); Chem. Abs. 47., 431
(1953).
(35) "Analysis of Parathion in Air by a Determination of Inorganic
Phosphate", 6. C. Richards, Occupational Health 12, 94-5 (1952);
Chem. Abs. 46, 83091 (1952).
(36) "A New Commercial Synthesis of the Insecticide Parathion", L. A. R.
Hall et al., Trans. Kansas Acad. Sci. 55, 131-7 (1952); Chem. Abs.
46, 8319e (1952).
(37) "Potentiometric Determination of 0,0-Diethyl-O-p-Nitrophenyl
Thiophosphate (E 605) or 0,0-Dlmethy1 0-p-Nitrophenyl Thiophosphate
in Commercial Preparations", M. Schonamsgruber, Z. Anal. Chem. 135,
23-36 (1952); Chem. Abs. 48, 3851h (1954).
i
(38) "The Rate of Hydrolysis of Some p-Nitrophenol Esters of Orthophosphoric
and Thiophosphoric Acids", J. A. A. Ketelaar et al., Rec. trav. chim.
71, 1253-8 (1952); Chem. Abs. 47, 8487b (1953).
185
-------
(39) "Esters of Phosphorous, Phosphoric, and Thiophosphoric Acids", Pest
Control Ltd., Brit. 668,536, Mar. 19, 1952; Chem. Abs. 47., 5438g
(1953).
(40) "Aryl Dialkyl Thiophosphates", Farbenfabriken Bayer, Brit. 670,030,
Apr. 9, 1952; Chem. Abs. 47., 5438i (1953).
(41) "0,0-Dialkyl 0-p-Nitrophenyl Phosphorothioates", Monsanto Chemical
Co., Brit. 684,839, Dec. 24, 1952; Chem. Abs. 48, 1415 (1954).
(42) "Esters of Phosphoric and Thiophosphoric Acid", Gebr. Borchers A.-G.
Ger. 848,041, Sept. 1, 1952; Chem. Abs. 48, 11482d (1954).
(43) "Purification of Parathion", F. I. Edwards, Jr. et al., U. S.
2,605,279, July 29, 1952; Chem. Abs. 46, 10525f (1952).
1953
(44) "Parathion", P. A. Giang, J. Assoc. Offie. Agr. Chemists 36, 384-7
(1953); Chem. Abs. 47., 12739 (1953).
(45) "The Isomerization of Organic Thionophosphate Insecticides", R. L.
Metcalf et al., J. Econ. Entomol. 46, 288-94 (1953); Chem. Abs. 48,
4166d (1954).
(46) "Parathion and Ultraviolet Light", J. Payton, Nature 171, 355-6 (1953);
Chem. Abs. 4£, 6466b (1953).
(47) "Reversed-Phase Paper Chromatography of Parathion and Related
Phosphate Esters", R. L. Metcalf et al., Science 117, 527-8 (1953);
Chem. Abs. 47_, 9550a (1953).
(48) "Ultraviolet Absorption Spectra of Compounds in Technical Parathion
and Dimethylparathion", Sokol, Chem. Zvesti 7, 429-38 (1953); Chem.
Abs. 48, 10988a (1954).
(49) "Determination and Control of Parathion", J. Schonberg, Actas y
Trabajos Congr. Peruano Quim. 395-400 (1953); Chem. Abs. 51, 4631h
(1957).
(50) "Determination of Parathion", Z. V. Ivanova, Gigiena i Sanit. No. 4,
29-34 (1953); Chem. Abs. 47, 11646g (1953).
(51) "Thiophosphate Esters", Pittsburgh Coke & Chemical Co., U. S.
2,657,229, Oct. 27, 1953; Chem. Abs. 48, 12805d (1954).
(52) "0,0-Dialkyl 0-p-Nitrophenyl Thiophosphates", Monsanto Chemical Co.,
U. S. 2,663,721, Dec. 22, 1953; Chem. Abs. 48, 137171 (1954).
186
-------
1954
(53) "Analysis of Parathion", P. A. Giang, J. Assoc. Offie. Agr. Chemists
37, 625-8 (1954); Chem. Abs. 48_, 11704g (1954).
(54) "Paper Chromatography of Some Organic Phosphate Insecticides. I.
New Spot Test", J. W. Cook, J. Assoc. Offic. Agr. Chemists 37, 984-7
(1954); Chem. Abs. 49, 2665b (1955).
(55) "Separation and Identification. II", Ibid. 987-9; Chem. Abs. 49_, 2665c
(1955).
(56) "Effects of Light on Systox and Isosystox. Ill", Ibid. 989-96; Chem.
Abs. .49, 2665d (1955).
(57) "Determination of Parathion", S. Schomberg, Chimie & Industrie 72,
444-6 (1954); Chem. Abs. 4£, 10569f (1955).
(58) "Examination of Parathion in Water, Vegetables, Fruits, etc. II",
I. Kawashiro et al., Bull. Natl. Hyg. Lab., Tokyo No. 73, 201-3
(1955); Chem. Abs. 50, 6703a (1956).
(59) "The Analysis of Emulsifiable Parathion Preparations", L. Westenberg,
Mededel. Landbouwhogeschool Wageningen 19, 554-7 (1954); Chem. Abs.
52, 12303d (1958).
(60) "Paper Chromatographical Separation of Contact Insecticides (DDT,
Parathion, BHC)", W. Gruch, Naturwissenschaften 41, 39-40 (1954);
Chem. Abs. 48, 10988d (1954).
(61) "Polarographic Determination of 0,0-Diethyl 0-p-Nitrophenyl Thio-
phosphate and 0-ethyl di(O-p-nitrophenyl) Thiophosphate in Technical
Parathion", J. Kovac, Chem. Zvesti 8, 590-5 (1954); Chem. Abs. 49_,
7177g (1955).
(62) "Note on the Paper by Ivanova 'Quantitative Determination of Parathion1",
N. N. Mel'nikov, Gigiena i Sanit. No. 6, 53 (1954); Chem. Abs. 48,
11712h (1954).
(63) "Thiophosphate Esters", Pittsburgh Coke & Chemical Co., U. S. 2,692,891,
Oct. 26, 1954; Chem. Abs. 49, 12537i (1955).
(64) "Organophosphoric Acid Esters", Nippon Soda Co., Japan 5085('54), Aug.
14; Chem. Abs. 50, 6507i (1956).
(65) "Organic Phosphoric Acid Esters", Nippon Soda Co., Japan 5881 ('54),
Sept. 14; Chem. Abs. 50, 7133c (1956).
(66) "Ultraviolet Spectrophotometric Determination of Paration in
Parathion Dust", M. Kotakemori, Ann. Kept. Takamine Lab. 6, 146-50
(1954); Chem. Abs. 49, 16307c (1955).
187
-------
1955
(67) "Parathion. Determination by Averell-Norris Method", P. A. Clifford,
J. Assoc. Offic. Agr. Chemists 38, 673-6 (1955); Chem Abs. 49,
16307a (1955).
(68) "Determination of Parathion in Pineapples", R. Santini, Jr. et al.,
J. Agr. Univ. Puerto Rico 38 (1954); Chem. Abs. 49, 16307b (1955).
(69) "Spectrophotometric Identification and Determination of Parathion",
A. I. Biggs, Analyst 80, 279-83 (1955); Chem. Abs. 49, 9865e (1955).
(70) ".[Analysis of] Parathion", P. A. Giang, J. Assoc. Offic. Agr. Chemists
38, 292-4 (1955); Chem. Abs. 49, 9865h (1955).
(71) "The Assay of E 605 (Parathion)", U. Paulus et al., Arzneimittel-
Forsch. _5, 241-4 (1955); Chem. Abs. 49_, 11229h (1955).
(72) "E-605 (Parathion). Determination in Commercial Preparations and
Proof in Inner Organs", L. Stoicheva et al., Nauch. Trudove Visshiya
Med. Inst. Sofia 3, No. 2, 215-25 (1955); Chem. Abs. 53, 16457d (1959).
(73) "Thermal Decomposition of Some Esters of Thiophosphoric Acid", Z. M.
Bakanova et al., Organ. Insektofungitsidy (Moscow: Gosudarst. Nauch.-
Tekh. Izdatel. Khim. Lit.) Sbornik 1955, 119-46; Chem. Abs. .53,
6129d (1959).
(74) "The Isomerization of Insecticidal Organic Thiophosphate and Seleno-
phosphate", V. Tichy, Chem. Zvesti 9, 3-18 (1955); Chem. Abs. 49,
13929c (1955).
1956
(75) "Thermal Decomposition of Some Phosphorothioate Insecticides", J. B.
McPherson, Jr. et al., J. Agr. Food Chem. 4, 42-9 (1956); Chem. Abs.
50, 4446d (1956).
(76) "Polymethine Dyes and Their Practical Application. Parathion", L.
Sassi, Arch. Inst. Pasteur Tunis 33, 429-50 (1956); Chem. Abs. 55,
2361b (1961). '
(77) "Analysis of E 695 by the Method of Schwerd and Schmidt", H. Schreiber,
Arch. Toxikol. 16, 129-33 (1956); Chem. Abs. 57., 7671h (1962).
(78) "Determination of 0,0-Diethyl 0-p-Nitrophenyl Thiophosphate (E 605)
with the Aid of Column Chromatography", W. Paulus et al., Arzneimittel-
Forsch. 6, 766-7 (1956); Chem. Abs. 51, 6067i (1957).
(79) "Determination of Parathion", A. Venturinl, Boll. Lab. Chlm. Provincial
(Bologna) 7, 147-50 (1956); Chem. Abs. 51, 10820b (1957).
188
-------
(80) "Determination of p-Nitrophenol in the Urine of Exposed Persons",
D. Vlachova, Pracovni Lekarstvi 8, 283-8 (1956); Chem. Abe. 51,
5180c (1957).
(81) "Microdetermination of Parathion in the Air and in Solution", Ibid.
289-91; Chem. Abs. 51, 5180d (1957).
1957
(82) "Color Reaction of 2,6-Dibromo-N-Chloro-p-Benzoquinone Imine with
Thiophosphate Insecticides on Paper Chromatograms", J. J. Menn et al.,
J. Agr. Food Chem. 5, 601-2 (1957); Chem. Abs. 51, 16989h (1957).
(83) "Quantitative Study of Cholinesterase-Inhibiting Decomposition
Products of Parathion Formed by Ultraviolet Light", J. W. Cook et al.,
J. Assoc. Offic. Agr. Chemists 40, 277-8 (1957); Chem. Abs. 51,
5349i (1957).
(84) "Reaction for Colorimetric Estimation of Some Phosphorus Compounds",
B. Gehauf et al., Anal. Chem. 29, 278-81 (1957); Chem. Abs. 51,
6423d (1957).
(85) "Qualitative Microdetermination of Organic Phosphorus Compounds",
C. M. Welch et al., Anal. Chem. 29, 874-7 (1957); Chem. Abs. 51,
11933i (1957).
(86) "Colorimetric Determination of Certain Organophosphorus Compounds
and Acylating Agents. Use of Diisonitrosoacetone Reagent", S. Sass
et al., Anal. Chem. 29, 1346-9 (1957); Chem. Abs. 52, 172f (1958).
(87) "[Determination of] Parathion", K. Helrich, J. Assoc. Offic. Agr.
Chemists 40, 747(1957); Chem. Abs. 51, 15875e (1957).
(88) "Microdetermination of Parathion", Y. Sumiki et al., Bull. Agr.
Chem. Soc. Japan 21, 204-6 (1957); Chem. Abs. 51, 15875h (1957).
(89) "Infrared Spectrophotometrie Determination of Traces of Parathion
in Water", Y. Sumiki et al., Bull. Agr. Chem. Soc. Japan 21, 329-31
(1957); Chem. Abs. 52, 5706g (1958).
(90) "Ultraviolet Absorption Spectrophotometrical Determination of
Parathion in Water", H. Kita et al., Bull. Tokyo Med. Dental Univ.
4, 379-83 (1957); Chem. Abs. 52, 14039e (1958).
(91) "Analysis of Pesticides by Paper Chromatography. I. Organic
Phosphate Insecticides", S. Nishiyama et al., Kagaku to Sosa 10,
No. 3, 1-4 (1957); Chem. Abs. 52, 11344c (1958).
(92) "Paper Chromatography of Parathion Using Filter Paper Impregnated
with Silicic Acid", M. Asakawa et al., Nippon Oyo-Dubutsu-Rontyu
Gakkaishi 1, 67-8 (1957); Chem. Abs. 52, 14954a (1958).
189
-------
(93) "Paper Chromatography of Parathlon and Related Compounds", H. Koike,
Nippon Oyo-Dobutsu-Kontyu Gakkaishi 1, 68-70 (1957); Chem. Abs. 52,
14954c (1958).
(94) "Use of the Polarographic Method in the Determination of Isomers
and Derivatives of 0,0-Diethyl 0-(p-Nitrophenyl)Thiophosphates After
Their Separation by Paper Chromatography", J. Kovac, Chem. Zvesti 11,
162-7 (1957); Chem. Abs. _51, 12420h (1957).
(95) "Paper-Chromatographic Determination of Diethyl p-Nitrophenyl Thio-
phosphate and of Sulfonamides", W. Paulus et al., Arzneimittel-
Forsch. 7, 520-3 (1957); Chem. Abs. 52, 660d (1958).
(96) "The Analysis of Thiophosphoric Acid Ester Preparations", H. Meltzer,
Nachrbl. Deut. Pflanzenschutzdienst (Berlin) 11, 178-80 (1957); Chem.
Abs. 54, 6392d (1960).
(97) "Chemical Determination of Parathion and Its Application to Biological
Material", K. B. Augustinsson, Acta Agr. Scand. 7, 165-89 (1957);
Chem. Abs. 52, 16682g (1958).
(98) "Determination of Parathion Vapor and Dust in the Atmosphere", J. C.
Gage, Anal. Chim. Acta. 17, 291-4 (1957); Chem. Abs. 52, 14952g (1958),
(99) "Sewage Water from the Manufacture of Parathion", G. A. Malov,
Vodosnabzhenie i Sanit. Tekh. No. 5, 31-3 (1957); Chem. Abs. 5_2,
7582h (1958).
1958
(100) "Spectrophotometric Determination of Parathion and p-Nitrophenol",
E. Hjelt et al., Analyst 83, 283-90 (1958); Chem. Abs. 52, 15819c
(1958).
(101) "Effect of Light on Chemical and Biological Properties of Parathion",
J. P. Frawley et al., J. Agr. Food Chem. 6, 28-30 (1958); Chem. Abs.
52, 7607c (1958).
(102) "Separation and Identification of Chlorinated Organic Pesticides by
Paper Chromatography. XI. A Study of 114 Pesticide Chemicals:
Technical Grades Produced in 1957 and Reference Standards", L. C.
Mitchell, J. Assoc. Offic. Agr. Chemists 41, 781-816 (1958); Chem.
Abs. 53, 2525b (1959).
(103) "Hydrolysis of the Alkyl Phosphate Bond in Certain Dialkyl Aryl
Phosphorothioate Insecticides by Rats, Cockroaches, and Alkali",
F. W. Plapp et al., J. Econ. Entomol. 51, 800-3 (1958); Chem. Abs.
55, 20307b (1961).
190
-------
(104) "Absorption Spectra as a Modern Method of Investigating Pesticides",
E. Bottini et al., Ann. Sper. Agrar. (Rome) 12, Suppl. Ixxvii-cx
(1958); Chem. Abs. 53, 16691a (1959).
(105) "Systematic Procedure for the Identification of Dangerous Drugs,
Poisons, and Narcotics by Ultraviolet Spectrophotometry", L. W.
Bradford et al., Mikrochlm. Acta 353-82 (1958); Chem. Abs. 53,
20693d (1959).
(106) "Determination of E 605 (Parathion) and Methyl-E 605 in Air", W.
Pilz, Mikrochim. Acta, 383-94 (1958); Chem. Abs. 53, 20639i (1959).
(107) "Chromatography of Organic Insecticides. I. Separation of Insecti-
cides on Phenylcellosolve-Treated Paper", T. Shishido et al.,
Nippon Nogei-kagaku Kaishi 32, 956-60 (1958); Chem. Abs. 53, 15455f
(1959).
(108) "Detection and Estimation of Parathion Residues in Foods", S. N.
Ultra et al., J. Inst. Chem. India 30, 321-5 (1958); Chem. Abs. 55.
16841b (1961).
(109) "Chemical Studies on Insecticides. VI. The Rate of Hydrolysis of
Some Phosphorus Acid Esters", J. A. A. Ketelaar et al., Rev. Trav.
Chim. 77, 973-81 (1958); Chem. Abs. 53, 10920a (1959).
(110) "Purification of Effluents in the Manufacture of 0,0-Diethyl-0-(4-
Nitrophenyl)-Thiophosphate", N. N. Mel'nikov et al., Org. Insekto-
fungitsidy i Gerbitsidy 50-4 (1958); Chem. Abs. , 10221i (1960).
(Ill) "Detoxication of Waste Water from the Production of Parathion", N.
N. Mel'nikov et al., Nauchn. Inst. po Udobr. i Insektofung., No. 158,
60-4 (1958); Chem. Abs. 57, 3221c (1962).
1959
(112) "Gas Chromatography of Pesticides", D. M. Coulson et al., J. Agr.
Food Chem. 7, 250-1 (1959); Chem. Abs. ^3, 19280d (1959).
(113) "Note on the Conversion of Some Organophosphate Pesticides to Less
Polar Compounds by Ultraviolet Light", J. W. Cook et al., J. Assoc.
Offie. Agr. Chemists 41, 211-12 (1959); Chem. Abs. 53, 9556b (1959).
(114) "Design and Construction of a Phosphate Insecticides Plant", B. F.
Greek et al., Ind. Eng. Chem. 51, 104-12 (1959); Chem. Abs. 53,
8522b (1959).
(115) "Qualitative Analyses of Organic Phosphorus Color Reactions and
Simple Detection", R. Sera et al., Kumamoto Med. J. 12, 193-213
(1959); Chem. Abs. 54, 11813d (1960).
191
-------
(116) "Qualitative Analysis of 17 Organophosphorus Compounds by Paper
Chromatography", A. Matsunaga et al., Ibid. 214-19; Chem. Abe. 54,
Il813e (1960).
(117) "Microdetermination of Parathion (and Related Compounds)", Yu-Shih
Chen, Bull. Assoc. Agr. Chem. Natl. Taiwan Univ. (Formosa) 8, 21-4
(1959); Chem. Abs. 53, 22707i (1959).
(118) "Toxicology of Parathion", J. L. Sunol. Rev. Fac. Cienc. Quim., Univ.
Nad. La Plata 31, 93-102 (1959); Chem. Abs. 54, 25577e (1960).
(119) "Detection of Thiophosphoric Esters", R. Fischer et al., Sci. Pharm.
27, 1-6 (1959); Chem. Abs. _53, 16830a (1959).
(120) "Analysis of Some Thiophosphoric Acid Ester Insecticides", E. Sandi,
Z. Anal. Chem. 167, 241-53 (1959); Chem. Abs. 53, 19284d (1959).
(121) "Polarographic Properties of Certain Organic Phosphorus Compounds",
L. M. Shapiro, Doklady Akad. Nauk. Belorus, S.S.R. 3, No. 4, 146-9
(1959); Chem. Abs. 55, 4200i (1961).
1960
(122) "Colorimetric Method for Determination of Parathion", K. Helrich,
J. Assoc. Offie. Agr. Chemists 43, 344-5 (1960); Chem. Abs. 54.
21622d (1960).
(123) "The Infrared Spectra of Organic Phosphate Pesticides and Their
Application to Some Problems in Phosphate Pesticide Analysis",
D. F. McCaulley et al., J. Assoc. Offic. Agr. Chemists 43, 710-17
(1960); Chem. Abs. 54, 23098d (1960).
(124) "Spot Test Detection of Esters of Noncarboxylic Acids", F. Feigl
et al., Chemist-Analyst 49, 13-14 (1960); Chem. Abs. 55, 18453b
(1961).
(125) "Detection of Plant Pesticides in Mixtures by Infrared Spectroscopy",
W. Fischer et al., Z. Anal. Chem. 172, 175-92 (1960); Chem. Abs. _54,
13525i (1960).
(126) "The Influence of Human Plasma Cholinesterase Activity and Inhibitor
Conversion In Vitro on the Enzymic Determination of Organophosphorus
Insecticides", K. Kojima et al., Bochu-Kagaku 25(1), 30-41 (1960);
Chem. Abs. 61, 2415g (1964).
(127) "Organic Insectofungicides. LII. Reaction of Aryl Dlchlorothio-
phosphates with Magnesium Ethoxide", Ya. A. Mandel'baum, (Sci.
Research Inst. Fertilizers and Insectofungicides, Moscow). Zhur.
Obshchei Khim. 30,194-7 (1960); Chem. Abs. 54, 22321d (1960).
(128) "Thiophos and Methaphos", N. N. Mel'nikov et al., U.S.S.R. 126,880,
Mar. 10, 1960; Chem. Abs. 54, 19597i (1960).
192
-------
1961
(129) "Chromatographic Identification of Some Organophosphate Insecticides",
H. F. MacRae et al., J. Assoc. Offic. Agr. Chemists 44, 207-11 (1961);
Chem. Abs. 55, 20296h (1961).
(130) "The Effect of Ultraviolet Light (2537 A) on 141 Pesticide Chemicals
by Paper Chromatography", L. C. Mitchell, J. Assoc. Offic. Agr.
Chemists 44, 643-712 (1961); Chem. Abs. 56, 3849e (1962).
(131) "Detection of Parathion by Rapid Paper Chromatography", M. Kchouk,
Arch. Inst. Pasteur Tunis 38, 51-5 (1961); Chem. Abs. 56, 2735d
(1962).
(132) "The Test for Quantitative Determination of Esters of Thiophosphoric
Acid in Biological Material", R. Fischer et al., Arch. Toxikol. 19,
119-40 (1961); Chem. Abs. 57., 17130c (1962).
(133) "Test for Parathion", H. Schreiber, Arch. Toxikol. 19, 141-2 (1961);
Chem. Abs. 57_, 5064g (1962).
(134) "Toxicological Detection and Determination of Thiophosphoric Acid
Esters. II", R. Fischer, Pflanzenschutz Ber. 27, 165-76 (1961); Chem.
Abs. 59_, 5677e (1963).
(135) "The Use of Thin-Layer Chromatography in Forensic Toxicology for the
Detection of Organic Compounds", M. Marigo, Arch. Rrimlnol. 128,
99-107 (1961); Chem. Abs. 56, 5068i (1962).
(136) "Identification of Ethylparathion. II", S. Takagi, Kagaku Reisatsu
Kenkyusho Hokoku 14, 219, 25(1961); Chem. Abs. _56, 10631g (1962).
(137) "Paper Chromatography of Parathion and Related Compounds Using Filter
Paper Impregnated with Silicic Acid", T. Niwase, Kagaku Keisatsu
Kenkyusho Hokoku 14, A16-8 (1961); Chem. Abs. 5]_, 26251 (1962).
(138) "Thin-Layer Chromatographic Detection of Insecticides", J. Bacumler
et al., Helv. Chim. Acta 44, 1162-4 (1961); Chem. Abs. 56, 12036a (1962)
1962
(139) "Polarographic Microdetermination of Parathion and Malathion in
Admixture", D. E. Ott et al., Analyst 87, 70-2 (1962); Chem. Abs.
5£, 8960e (1962).
(140) "Esterase Inhibition Technique for the Detection of Organophosphorus
Pesticides", W. P. McKinley et al., J. Assoc. Offic. Agr. Chemists
45, 467-73 (1962); Chem. Abs. 57., 3821b (1962).
193
-------
(141) "Determination of Thiophosphoric Acid Derivatives and Related Compounds
on Chromatograms", H. Petschik et al., J. Chromatog. 7, 135-6 (1962);
Chem. Abs. 57, 6614b (1962).
(142) "Determination of Parathion", H. H. Lausen, Nature 194, 1174(1962);
Chem. Abs. 57_, 8962i (1962).
(143) "Paper-Chromatographic Studies on the Effect of Ultraviolet Light on
Parathion and Its Derivatives", P. Koivistoinen et al., Acta. Agr.
Scand. 12, 267-76 (1962); Chem. Abs. 59, 4492g (1963).
(144) "Determination of Parathion by Ultraviolet Spectrophotometry",
E. Imparato-Gargano et al., Ann. Fac. Sci. Agrar., Univ. Studi Napoli
Portici 28, 239-48 (1962-3); Chem. Abs. 61, 13817h (1964).
(145) "The Determination of Organic Phosphorus Insecticides", N. Faderl,
Mitt. Gebiete Lebensm. Hyg. 53, 154-75 (1962); Chem. Abs. 57., 17125e
(1962).
(146) "Thin-Film Chromatography in the Analysis of Insecticide Residues",
T. Salo et al., Z. Lebensm.-Untersuch.-Forsch. 117, 369-71 (1962);
Chem. Abs. 57, 12957e (1962).
(147) "Analysis of Insecticides. I. Separation and Identification of
Parathion and Its Related Compounds by Chromatography", S. Inoue,
Keisatsu Kenkyusho Hokoku 15, 68-70 (1962); Chem. Abs. 57. 6360c (1962)
(148) "Identification of Parathion in Biological Material", T. Kitaguehi
(Kumamoto Pref. Police Headquarters), Kagaku Keisatsu Kenkyusho
Hokoku 15, 71-2 (1962); Chem. Abs. 57, 7555h (1962).
(149) "Detection and Determination of Phosphate-Ester Insecticides in Plant
Materials", E. Sandi et al., Elelmiszervizsgalati Kozlemeny 8(1-2),
17-27 (1962); Chem. Abs. 64, 8866b (1966).
1963
(150) "Chromatographic Identification of Some Organophosphate Insecticides
in the Presence of Plant Extracts", H. F. MacRae et al., J. Agr.
Food Chem. 11, 174-8 (1963); Chem. Abs. 58, 11907d (1963).
(151) "The Analysis of Micro Amounts of Binapacryl, EPN, Methylparathion,
and Parathion", D. A. George, J. Assoc. Offie. Agr. Chemists 46(6),
960-3 (1963); Chem. Abs. 60, 4711a (1963).
(152) "Electron-Attachment Determination of Thiophosphate Pesticides in
the Picogram Range", D. L. Petitjean et al., J. Gas Chromatog. 1(2),
23 (1963); Chem. Abs. 59, 9253d (1963).
194
-------
(133) "Analysis of Organophosphorus, Organochlorine Insecticide Residues
in Food by Gas Chromatography", T. Nlshimoto et al., Shokuhin
Eiseigaku Zasshi 4, 192-7 (1963); Chem. Abs. 60, 4690a (1964).
(154) "Thiophosphate. 0,0-Diethyl O-(p-Nitrophenyl) Thiophosphate. 0,0-
Dimethyldithiophosphorylacetic Acid N-Methylamide", R. Pirisi et al.,
Rend. Seminario Fac. Sci. Univ. Cagliari 33, 81-102 (1963); Chem.
Abs. 66, 18546a (1967).
(155) "Decolorizing and Purifying 0,0-Dialkylthiophosphoryl Chlorides and
Thiophosphate Condensates Formed Therefrom", American Cyanamid Co.,
U. S. 3,098,866, July 23, 1963; Chem. Abs. 60, 408f (196 ).
(156) "Phosphoric Acid Esters", Geigy Chemical Corp., U. S. 3,107,245,
Oct. 15, 1963; Chem. Abs. 60, 2966f (1964).
(157) "Organic Thiophosphates", Osaka Kinzoku Kogyo Co., Ltd. Japan
26,366('63), Dec. 16; Chem. Abs. , 5554b (1964).
1964
(158) "Gas Chromatography Retention Times and Sensitivity Data for Insecti-
cides and Herbicides", E. J. Bonelli et al., J. Agr. Food Chem. 12(4),
333-6 (1964); Chem. Abs. 61, 7635f (1964).
(159) "Collaborative Comparison of Colorimetric and Potentiometric Methods
for Parathion and Methyl Parathion in Formulations", K. Helrich,
J. Assoc. Office Agr. Chemists 47(2), 242-4 (1964); Chem. Abs. 60,
16441f (1964).
(160) "Parathion", G. L. Sutherland, Anal. Methods Pesticides, Plant Growth
Regulators and Food Additives (G Zweig, Editor), Academic ,2 (1964);
Chem. Abs. 61, 11264e (1964).
(161) "Thin-Layer Chromatography of Organophosphorus Pesticides and Acids
on Microchromatoplates", C. W. Stanley, J. Chroma tog. 16(3), 467-75
(1964); Chem. Abs. 62, 11090a (1964).
(162) "Detection and Separation of the Most Important Organophosphorus
Pesticides by Thin-Layer Chromatography", M. Salame, J. Chromatog.
16(3), 476-80 (1964); Chem. Abs. 62, 11090b (1965).
(163) "Analyses of Organophosphorus Pesticides", W. P. McKinley, Proc. Can.
Soc. Forensic Sci. 2(2), 433-48 (1964); Chem. Abs. 61, 7638c (1964).
(164) "Applications of the Microcoulometric Titrating System as a Detector
in Gas Chromatography of Pesticide Residues", J. A. Challaombe et al.,
Residue Rev. 5, 57-72 (1964); Chem. Abs. 61, 9975h (1964).
195
-------
(165) "Thin-Layer Chromatography in the Determination of Pesticide
Residues", R. A. Conkin, Residue Rev. 6, 136-61 (1964); Chem. Abe.
61, 9976f (1964).
(166) "Detection of Insecticidal Phosphoric Acid Esters and Their Hydrolytic
Cleavage Products", H. W. Rahn et al., Pharmazie 19(9), 597-602
(1964); Chem. Abs. 61, 16719e (1964).
(167) "Characteristic Infrared Absorption Frequencies of Organophosphorus
Compounds. I. Phosphoryl (P:0) Group", L. C. Thomas et al.,
Spectrochim. Acta 20(3), 467-87 (1964); Chem. Abs. 60, 8783f (1964).
(168) "The Determination of Traces of Phosphoric Esters by Oxcillographic
Polarography", P. Nangniot, Anal. Chlm. Acta 31(2), 166-74 (1964);
Chem. Abs. 61, 12563b (1964).
(169) "Colorimetric Determination of Parathion in Plants Based on Phosphorus
Content", I. Balinov, Gradinar. Lozar. Nauka (Sofia), 1(10), 41-4
(1964); Chem. Abs. 62, 13783a (1965).
(170) "Detection and Identification of the Residues of the Organophosphorus
Pesticides by Gel Electrophoresis", P. Bruaux et al., Ann. Biol. Clin.
(Paris), 22(3-4), 375-98 (1964); Chem. Abs. 61, 6303a (1964).
(171) "Pesticide Residues. Use of an Aerograph Flame lonization Detector
as a Thermionic Detector. Application to Organophosphate Insecticide
Research", R. Mestres et al., Trav. Soc. Pharm. Montpellier 24(4),
283-303 (1964); Chem. Abs. 63, 13970d (1965).
(172) "Detection and Determination of Parathion by Gas Chromatography with
an Electron-Capture Detector", F. Lodi, Farmaco (Pavia), Ed. Prat.
19(11), 560-6 (1964); Chem. Abs. 62, 5824b (1965).
(173) "Determination of Some Organophosphorus Insecticides by Gas-Liquid
Partition Chromatography", M. Horiguchi et al., Chem. Pharm. Bull.
(Tokyo) 12(11), 1315-19 (1964); Chem. Abs. 62, 5823g (1965).
(174) "Evaluation of Minute Amounts of Some Phospho-Organic Compounds in
Plant Material by Means of Paper Chromatography", J. Zadrozinska,
Roczniki Panstwowego Zakladu Hig. 15(1), 5-12 (1964); Chem. Abs. 61,
6262a (1964).
1965
(175) "Thin-Layer Chromatography and Cholinesterase Detection of Several
Phosphorothiono Insecticides and Their Oxygen Analogs", A. El-Refal
et al., J. Agr. Food Chem. 13(5), 477-81 (1965); Chem. Abs. 63,
13968c (1965).
196
-------
(176) "Simultaneous and Selective Detection of Phosphorus, Sulfur, and
Halogen in Pesticides by Microcoulometric Gas Chromatography", H. P.
Burchfield et al., J. Agr. Food Chem. 13(6), 511-16 (1965); Chem.
Abs. 64, 4193b (1966).
(177) "Determination of Organophosphorus Insecticide Residues Using the
Emission Spectrometric Detector", C. A. Bache et al., Anal. Chem.
37(12), 1477-80 (1965); Chem. Abs. 64, 1288a (1966).
(178) "The Identification and Determination of Chlorinated Pesticide Residues",
J. H. Hamence et al., Analyst 90(1076), 649-56 (1965); Chem. Abs.
64, 8864g (1966).
(179) "Identification of Trace Amounts of Organophosphorus Pesticides by
Frustrated Multiple Internal Reflectance Spectroscopy", T. S. Hermann,
App. Spectry. 19(1), 10-14 (1965); Chem. Abs. 62, 12387b (1965).
(180) "Extraction p-Values of Pesticides and Related Compounds in Six
Binary Solvent Systems", M. C. Bowman et al., J. Assoc. Offie. Agr.
Chemists 48(5), 943-52 (1965); Chem. Abs. 64, 4192h (1966).
(181) "A Sweep Codistillation Cleanup Method for Organophosphate Pesticides.
I. Recoveries from Fortified Crops", R. W. Storherr, J. Assoc. Offie.
Agr. Chemists 48(6), 1154-8 (1965); Chem. Abs. 64, 8847d (1966).
(182) "A Sweep Codistillation Cleanup Method for Organophosphate Pesticides.
II. Rapid Extraction Methods for .Crops", R. Watts et al., J. Assoc.
Offie. Agr. Chemists 48(6), 1158-60 (1965); Chem. Abs. 64, 8847f (1966).
(183) "Titrimetric Determination of Parathion with Chloramine-T", V.
Laxminarayana et al., Chemist-Analyst 54(1), 9-10 (1965); Chem. Abs.
62, 9713f (1965).
(184) "Electrolytic Conductivity Detector for Gas Chromatography", D. M.
Coulson, J. Gas Chromatog. 3(4), 134-7 (1965); Chem. Abs. 63, 6238f
(1965).
(185) "Simplified Gas Chromatographic Analysis of Pesticides from Blood",
N. C. Jain et al., J. Pharm. Pharmacol. 17(6), 362-7 (1965); Chem.
Abs. 63, 6257d (1965).
(186) "Simplified Gas-Chromatographlc Analysis of Pesticides from Blood",
P. L. Kirk et al., Proc. Can. Soc. Forensic Sci. A, 155-65 (1965);
Chem. Abs. 63, 12251c (1965).
(187) "Colorimetric Determination of Diethyl-p-Phenylthiophosphate in
Biological Material", T. Tsvetkova, Vet. Med. Nauki (Sofia) 2(2),
157-62 (1965); Chem. Abs. 63, 4867e (1965).
(188) "Gas-Liquid Chromatography of Organophosphorus Pesticides", J.
Kanazawa et al., Agr. Biol. Chem. (Tokyo) 29(1), 56-60 (1965); Chem.
Abs. 62, 12385a (1965).
197
-------
(189) "Detection of Pesticides by a Combination of Two-Channel Gas
Chromatography and Spectrophotometry", H. Brandenberger et al.,
Mitt. Gebiete Lebensm. Hyg. 56(4), 281-92 (1965); Chem. Abs. 64,
18340c (1966).
(190) "Determination of Selected Phosphoorganlc Pesticides (Parathion,
Methylparathion, Diazinon, Halation, Gusathion, Meta-Systox, and
Dipterex) by Thin-Layer Chromatography Method", J. Zadrozinska,
Roczniki Panstwowego Zakladu Hig. 16(4), 397-405 (1965); Chem. Abs.
64, 2684h (1966).
(191) "Toxlcological Analysis of Organic Phosphorus Insecticides" A. S.
Santos et al., Rev. Port. Farm. 15(3), 367-74 (1965); Chem. Abs. 64,
11794d (1966).
(192) "Polarographic Method for Determination of Thiophos in Plant Samples",
F. I. Potrashku, Tr. Vses. Nauchn.-Issled.Inst. Zashchity Rast. (24),
140-3 (1965); Chem. Abs. 65, 19246d (1966).
(193) "Relation Between the Structure and Chromatographic Properties of
Organophosphorus Compounds", V. Batora, Khlm. Primen. Fasfororg.
Soedin., Tr. Vses. Konf., 3rd 333-7 (1965); Chem. Abs. 77., 74650y
(1972).
(194) "Oxidation of Phosphorothionates with Dinitrogen Tetroxide", American
Cyanamid Co., U. S. 3,225,044, Dec. 21, 1965; Chem. Abs. 64, 6560f
(1966).
1966
(195) "Apparatus and Procedures for Rapid Extraction and Identification of
Pesticides by Single and Multiple Distribution in Binary Solvent
Systems", M. Beroza et al., Anal. Chem. 38(7), 837-41 (1966); Chem.
Abs. £5, 7930f (1966).
(196) "Gas Chromatographic Column for Pesticide Residue Analysis; Retention
Times and Response Data", J. A. Burke et al., J. Assoc. Offic. Anal.
Chemists 49(2), 374-85 (1966); Chem. Abs. 65, 2894g (1966).
(197) "Rapid Screening for Some Anticholinesterase Insecticide Residues by
Automated Analysis", D. E. Ott et al., J. Assoc. Offic. Anal. Chemists
49(3), 662-9 (1966); Chem. Abs. 65, 6181e (1966).
(198) "Automated Elution-Filtration Analysis of Anticholinesterase Organo-
phosphorus Compounds on Thin Layer Chromatographic Scrapings", D. E.
Ott et al., J. Assoc. Offic. Anal. Chemists 49(3), 669-74 (1966);
Chem. Abs. 65, 6181e (1966).
(199) "Mass Spectra of Some Organophosphorus Pesticide Compounds", J. N.
Damico, J. Assoc. Offic. Anal. Chemists 49(5), 1027-45 (1966); Chem.
Abs. 66, 1834k (1967).
198
-------
(200) "Separation and Detection of Submicrogram Quantities of Pesticides
by an Improved TLC Technique", H. Beckman et al., Bull. Environ.
Contain. Toxicol. 1(3), 78-85 (1966); Chem. Abs. 65_, 7894e (1966).
(201) "Sodium Flame Detector of Increased Stability for Phosphorus-
Containing Pesticides", D. R. Coahran, Bull. Environ. Contain.
Toxicol. 1(4), 141-8 (1966); Chem. Abs. 65_, 17623d (1966).
(202) "Phosphorus Detector for Pesticides Analysis", C. H. Hartmann,
Bull. Environ. Contam. Toxicol. 1(4), 159-68 (1966); Chem. Abs. 65,
17623e (1966).
(203) "Treating Parathion Wastes", C. N. Stutz, Chem. Eng. Progr. 62(10),
82-4 (1966); Chem. Abs. 66, 5598u (1967).
(204) "Flame Photometric Detector. Application of a Specific Detector for
Phosphorus and for Sulfur Compounds Sensitive to Subnanogram Quantities",
S. S. Brody et al., J. Gas. Chromatog. 4(2), 42-6 (1966); Chem. Abs.
64, 13378b (1966).
(205) "Treatment of Parathion Wastes and Other Organics", G. Coley et al.,
J. Water Pollution Control Federation 38(8), 1345-9 (1966); Chem. Abs.
65, 19833f (1966).
(206) "Modification of the Zeumer-Fischer Method for Determining Aromatic
Organophosphorus Preparations", N. Buchvarova et al., Vet. Med. Nauki
(Sofia) 3(5),.513-18 (1966); Chem. Abs. 66, 16975v (1967).
(207) "Gas-Chromatographic Separation of 0,0-Dialkyl 0-(4-Nitrophenyl)
Thiophosphates", J. Urivnak et al., Collection Czech. Chem. Commun.
31(8), 3402-5 (1966); Chem. Abs. 65, 12799h (1966).
(208) "The Infrared Spectroscopic Detection of Plant Protective Agents
from Organic Material", G. Doering et al., Deut. Z. Ges. Gerichtl.
Med. 57(1-2), 341-52 (1966); Chem. Abs. 65, 7932e (1966).
(209) "Analysis of Phenoxy Compounds. II. Paper Chromatographic Detection
of Several Active Substances with the Phenyl-Ester Group", R.
Giebelmann, Pharmazie 21(3), 171 (1966); Chem. Abs. 65, 5305e (1966).
(210) "Schoenemann Reaction for the Detection of Thiophosphates", Kh. Lohs
et al., Z. Chem. 6(6), 224 (1966); Chem. Abs. 65, 11324b (1966).
(211) "Thin-Layer Chromatography of Pesticides", T. Salo et al., Z. Lebensm.-
Untersuch.-Forsch. 129(3), 149-53 (1966); Chem. Abs. 64, 20546d
(1966).
(212) "Identification and Quantitative Determination of Parathion in Sub-
nanogram Amounts in Biological Materials by Gas Chromatography with
an Electron-Capture Detector (Strontium 90). Control of Para-oxon
by Means of a Biological Test", C. Crasso et al., Ric. Sci. 36(10),
1083-6 (1966); Chem. Abs. 66, 75253f (1967).
199
-------
(213) "Residue Analysis of Agricultural Chemicals. III. Electron-Capture
Gas Chromatography of Various Pesticides", J. Kanazava, Nippon Mogel
Kagaku Kaishl 40(4), 178-84 (1966); Chen. Abe. 65, 4571e (1966).
(214) "Gas Chromatographic Analysis of Pesticides. II. Gas Chromatographic
Determination of Organophosphorus Pesticides", H. Takehara et al.,
Nippon Nogel Kagaku Kalshl 40(11), 394-400 (1966); Chen. Abe. 66,
94159w (1967).
1967
(215) "Colorimetrlc Analysis of Malathion and Parathion Using Fluoboric
Acid", D. E. Long. Anal. Lett. 1(2), 61-5 (1967); Chem. Abs. 68.
38473y (1968).
(216) "Direct Fluorescent Detection of Organothlophoaphorus Pesticides
and Some of Their Sulfur-Containing Breakdown Products After Thin-
Layer Chromatography", M. T. H. Kagab, J. Ass. Offie. Anal. Chem.
50(5), 1088-98 (1967); Chem. Abs. 67,, 99119p (1967).
(217) "A Rapid Micromethod of Sample Cleanup for Gas Chromatographic
Analysis of Insecticidal Residues in Plant, Animal, Soil, and Surface
and Ground Water Extracts", A. M. Kadoum, Bull. Environ. Contam.
Toxicol. 2(5), 264-73 (1967); Chem. Abs. 67_, 99128r (1967).
(218) "Improved Gas Chromatographic Systems for Determining Organochlorine
Pesticide Residues in Wildlife", J. H. Simmons et al., J. Chromatogr.
27(1), 253-5 (1967); Chem. Abs. 67, 10437v (1967).
(219) "Reversed Phase Paper Chromatography of p-Mitrophenyl Methylphosphonates
and Sulfur Analogs", A. Verweij et al., J. Chromatogr. 30(1), 163-9
(1967); Chem. Abs. 67, 104948q (1967).
(220) "Gas-Liquid Chromatographic Separation of Some Organophoephate Pesti-
cides, Their Hydrolysis Products, and Oxons", I. H. Suffet et al.,
Environ. Scl. Technol. 1(8), 639-43 (1967); Chem. Abs. 67, 107614p
(1967). ~~
(221) "Modified Hydrogen Flame-Ionlration Detector, Highly Sensitive and
Selective for Phosphates", R. V. Hoffman, Lect. Gas Chromatogr.
137-47 (1967); Chem. Abs. 70, 95709v (1969).
(222) "Systematic Applications of Gas-Liquid Chromatography in Toxicology.
V. Pesticides and Evaluation of Toxic Levels", N. C. Jain et al.,
Mlcrochem. J. 12(2), 265-72 (1967); Chem. Abs. 67, 42144p (1967).
(223) "Thin-Layer and Gas Chromatographic Analysis of Parathion and Methyl
Parathion In the Presence of Chlorinated Hydrocarbons", F. K.
Kawahara et al., J. Water. Pollut. Contr. Fed. 39(3), 446-57 (1967);
Chem. Abs. 67, 36192m (1967).
200
-------
(224) "Gas Chromatographic Determination of Residues of £605 Products and
Agrltox in Plants and Soil Samples", E. Moellhoff, Pflanzenschutz-
Nachr. "Bayer" 20(2), 557-74 (1967); Chem. Abs. 70, 27727z (1969).
(225) "Thin-Layer Chromatographic Separation Scheme for Insecticidally
Active Phosphoric Acid Esters", J. A. Guth, Pflanzenschutzberichte
35(9-10), 129-43 (1967); Chem. Abs. 67, 72784q (1967).
(226) "Gas-Chromatographlc Determination of Parathion and MalathIon",
S. Yoshida, Else! Kagaku 13(5), 254-7 (1967); Chem. Abs. 68,
94857p (1968).
(227) "Determination of Some Organophosphorus Compounds in Biological
Material by a Paper Chromatographic Method", R. V. Mishina, Sud.-
Med. Ekspert. Krimlnallstika Sluzhbe Sledstviya, No. 5, 651-4
(1967); Chem. Abs. .73* 76027s (1970).
(228) "Separation and Identification of Some Organophosphate Insecticides
by Thin-Layer Chromatography and Their Determination After Conversion
into Orthophosphate", D. Pantovic, Hrana Ishrana 8(11-12), 769-71
(1967); Chem. Abs. 69, 66429c (1968).
(229) "0,0-Dialkyl 0-aryl Thlophosphates", Gelgy Chemical Corp., U. S.
3,329,678, July 4, 1967; Chem. Abs. .67, 108664s (1967).
1968
(230) "Enzymlc Detection of Ten Organophosphorus Pesticides and Carbaryl
on Thin-Layer Chromatograms: An Evaluation of Indoxyl, Substituted
Indoxyl, and 1-Naphthyl Acetates as Substrates of Esterases",
C. E. Mendoza et al., Analyst (London) 93(1102), 34-8 (1968);
Chem. Abs. 68, 58668u (1968).
(231) "Procedure for Semlquantltative Confirmation of Some Organophosphorus
Pesticide Residues In Plant Extracts", P. J. Wales et al., Analyst
(London) 93(1111), 691-3 (1968); Chem. Abs. 22, 10567z (1969).
(232) "Detection of Chollnesterase-Inhibltlng Pesticides Following Separa-
tion on Thin-Layer Chromatograms", W. Winterlin et al., J. Agr. Food
Chem. 16(5), 808-12 (1968); Chem. Abs. £9, 95350a (1968).
(233) "Nuclear Magnetic Resonance Studies of Phosphorus (V) Pesticides.
I. Chemical Shifts of Protons as a Means of Identification of
Pesticides", H. Babad et al., Anal. Chlm. Acta. 41(2), 259-68
(1968); Chem. Abs. 68, 7718lw (1968).
(234) "Collaborative Study of Three Gas Chromatographic Dual Detection
Systems for Analysis of Multiple Chlorinated and Organophosphorus
Pesticides", J. R. Wessel, J. Ass. Offic. Anal. Chem. 51(3), 666-75
(1968); Chem. Abs. 69, 9900a (1968).
(235) "High-Resolution NMR Spectra of Pesticides. I. Organophosphorus
Pesticides", L. H. Keith et al., J. Ass. Offic. Anal. Chem. 51(5),
1063-94 (1968); Chem. Abs. 69, 75849s (1968).
201
-------
(236) "Thin-Layer Chromatography of Organophosphorus Insecticides with
Several Adsorbents and Ternary Solvent Systems", M. E. Getz et al.,
J. Ass. Offie. Anal. Chem. 51(5), 1101-7 (1968); Chem. Abs. 69,
75850k (1968).
(237) "Versatility of OV-17 Substrate for Gas Chromatography of Pesticides",
C. A. Bache et al., J. Ass. Offic. Anal. Chem. 51(6), 1270-1 (1968);
Chem. Abs. _70, 27907h (1969).
(238) "Cleanup Procedure for Water, Soil, Animal, and Plant Extracts for
the Use of Electron-Capture Detector in the Gas Chromatographic
Analysis of Organophosphorus Insecticide Residues", A. M. Kadoum,
Bull. Environ. Contain. Toxicol. 3(4), 247-53 (1968); Chem. Abs. 69.
75644w (1968).
(239) "The Effect of the Column Support Material on the Gas-Chromatographic
Resolution of Methyl Parathion, Ethyl Parathion, Ethyl Para-oxon,
Malathion, and Lalaoxon", A. Bevenue et al., J. Chromatogr. 35(1),
17-23 (1968); Chem. Abs. ,69, 18246u (1968).
(240) "Thin-Layer Chromatographic-Enzyme Detection of Organophosphorus
Insecticides. Activation of Weak Esterase Inhibitors", H.
Ackermann, J. Chromatogr. 36(3), 309-17 (1968); Chem. Abs. 69,
105284y (1968).
(241) "Use of Hydriodic Acid in the Detection of Pesticides After Thin-
Layer Chromatography", J. Askew et al., J. Chromatogr. 37(2), 369-
72 (1968); Chem. Abs. 2P_, 10572x (1969).
(242) "Microwave-Powered Emission Determination of Residues of Organic
Bromine, Chlorine, Iodine, Phosphorus, and Sulfur Pesticides in a
Helium Plasma", C. A. Bache et al., Biomed. Appl. Gas. Chromatogr.
2, 165-78 (1968); Chem. Abs. 73, 76019r (1970).
(243) "Automated Differential Screening Method for Organophosphorus
Pesticides", D. C. Leegwater et al., J. Sci. Food Agr. 19(9), 513-18
(1968); Chem. Abs. 69, 95147q (1968).
(244) "The Use of Gas Chromatography With Electron Capture in the Analysis
of Organophosphate Pesticides", M. Salame, Ann. Bio. Clin. (Paris)
26(7-9), 1011-21 (1968); Chem. Abs. 69, 105280u (1968).
(245) "Detection of Pesticides by Reversed Phase Paper Chromatography",
R. T. Wang et al., Chung Kuo Nung Yeh Hua Hsueh Hui Chih 6(3-4),
63-8 (1968); Chem. Abs. 71, 111799c (1969).
(246) "Use of An Electron-Capture Detector in Gas Chromatography. III.
Example of Its Application. Study of the Response of Some Chlorinated
and Phosphorylated Pesticides", P. Devaux, et al., Bull. Soc. Chim.
Fr. (4), 1627-33 (1968); Chem. Abs. 69, 26229f (1968).
202
-------
(247) "Determination of Parathion and Methylparathlon in Food", I. Camoni
et al., Boll. Lab. Chim. Prov. 19(5), 615-29 (1968); Chem. Aba. JO,
95491t (1969).
(248) "Microdetennination of Parathlons by Thermo- and Ultraviolet
Decomposition Products", Y. Doi et al., Acta Med. Okayama 22(5),
281-91 (1968); Chem. Abs. 71, 59971m (1969).
(249) "Qualitative Analysis of Synthetic Organic Pesticides by Spot Tests",
M. Kanda et al., Nippon Hoigaku Zasshi 22(3), 229-51 (1968); Chem.
Abs. 21, 65726x (1970).
(250) "Ultraviolet Spectral Analysis of Parathion Emulsifiable Liquids",
R. Carrasquero, Agron. Trop. (Marcay, Venez.) 18(3), 363-7 (1968);
Chem. Abs. 71, 59972n (1969).
(251) "Phosphoric Esters of Substituted Hydroxypyrimidines and Phenols",
Geigy Chemical Corp., U. S. 3,367,935, 06 Feb 1968; Chem. Abs. 69,
27454n (1968).
1969
(252) "Identification of Pesticides in Mixtures by High-Resolution Mass
Spectrometry", R. E. Lovins, J. Agr. Food Chem. 17(3), 663-7 (1969);
Chem. Abs. .71, 29523z (1969).
(253) "Pesticide Residues. Recovery of 65 Organophosphorus Pesticides
from Florisil With a New Solvent-Elution System", H. Beckman et al.,
J. Ass. Offic. Anal. Chem. 52(2), 286-93 (1969); Chem. Abs. 22.,
86520z (1969).
(254) "Gas Chromatography of Organophosphorus Pesticides: Retention Times
and Response Data on Three Columns", R. R. Watts et al., J. Ass.
Offic. Anal. Chem. 52(3), 513-21 (1969); Chem. Abs. 71, 12019s (1969).
(255) "Alkaline Precolumn for Use in Gas-Chromatographic Pesticide Residue
Analysis", G. A. Miller et al., J. Ass. Offic. Anal. Chem. 52(3),
548-53 (1969); Chem. Abs. .71, 12021m (1969).
(256) "Collaborative Study of Confirmative Procedures by Single-Sweep
Oscillographic Polarography for the Determination of Organophosphorus
Pesticide Residues in Nonfatty Foods", R. J. Gajan, J. Ass. Offic.
Anal. Chem. 52(4), 811-17 (1969); Chem. Abs. 7JL, 79813q (1969).
(257) "Polyamide-Layer Chromatography of Organophosphorus Pesticides",
K. Nagasawa et al., J. Chromatogr. 39(3), 282-90 (1969); Chem. Abs.
JO, 114093h (1969).
(258) "Identification of Organophosphate Pesticides by Gas Chromatography
with the Flame Photometric Detector", C. W. Stanley et al., J.
Chromatogr. 40(2), 289-93 (1969); Chem. Abs. 70, 114094J (1969).
203
-------
(259) "Simple and Rapid Separation of Pesticides by Polyamide Chroma-
tography", R. T. Wang et al., J. Chromatogr. 42(3), 416-18 (1969);
Chem. Abs. 71, 59980p (1969).
(260) "Thin-Layer Chromatographic-Enzymic Detection of Organophosphorus
Insecticides. Thin-Layer Chromatographic Behavior of Some Other
Insecticides", H. Ackermann, J. Chromatogr. 44(2), 414-18 (1969);
Chem. Abs. _72, 779lOr (1970).
(261) "Determination of Organophosphorus Pesticides in Water", G. Zweig
et al., Residue Rev. 26, 17-36 (1969); Chem. Abs. 71, 80107u (1969).
(262) "Chromatographic Determination of Trace Amounts of Pesticide
Residues", M. Beroza et al., Trace Subst. Environ. Health-3, Proc.
Univ. Mo. Annu. Conf., 3rd 331-51 (1969); Chem. Abs. J4, 2963t
(1971).
(263) "Phosphorimetric Determination of Some Organophosphate Pesticides",
E. A. Martin, Can. J. Pharm. Sci. 4(2), 47-50 (1969); Chem. Abs.
_72, 20802c (1970).
(264) "Simple and Rapid Reversed Phase Thin-Layer Chromatography of
Pesticides", R. T. Wang et al., Hua Hsueh (4), 80-5 (1969); Chem.
Abs. .74, 2953q (1971).
(265) "Isolation of Pesticide Traces from Water", F. Herzel (Ger.).
Staedtehygiene 20(12), 301-9 (1969); Chem. Abs. J2, 120361b (1970).
(266) "Separation and Identification of Parathion and Its Metabolite
p-Nitrophenol in lexicological Analysis by Thin-Layer Chromatography",
S. N. Tewari et al., Fresenius' Z. Anal. Chem. 248, 41 (1969); Chem.
Abs. .72, 53994v (1970).
(267) "Analysis of Chlorinated and Organic Phosphorus Pesticides by Gas
Chromatography", M. Randa et al., Nippon Hoigaku Zasshi 23(6),
477-86 (1969); Chem. Abs. 21» 65310c (1970).
(268) "p-Nitrophenol and Parathion Determination in Some Biological
Materials and Foods", C. Ghimicescu et al., Rev. Roum. Biochim.
6(3), 207-12 (1969); Chem. Abs. .72, 89164p (1970).
(269) "Detection of Methylnitrophos and Thiophos in Animal Meat, Milk
and Tissues by Thin-Layer Chromatography", T. G. Abbasov, Tr., Vses.
Nauch.-Issled. Inst. Vet. Sanit. 32, 313-16 (1969); Chem. Abs. TU,
30788h (1971).
204
-------
1970
(270) "Chemical Stability of Some Organic Phosphorus Pesticides in Aquatic
Environments11, S. D. Faust et al., Amer. Chem. Soc. Div. Water,
Air Waste Chem., Gen. Pap. 10(2), 142-7 (1970); Chem. Abs. 21.
84234e (1972).
(271) "Channel Layer Chromatography, With a Rapid Spotting Technique,
for One-Stage Cleanup in Pesticide Residue Analysis", R. M.
Hetherington, et al., J. Ass. Offic. Anal. Chem. 53(1), 146-8
(1970); Chem. Abs. 12.* 77840t (1970).
(272) "Report on Phosphated Pesticides", K. A. McCully, J. Ass. Offic.
Anal. Chem. 53(2), 363-5 (1970); Chem. Abs. ]2_, 131144J (1970).
(273) "GLC [Gas-Liquid Chromatographic] Retention Times of Pesticides
and Metabolites Containing Phosphorus and Sulfur on Four Thermally
Stable Columns", M. C. Bowman et al., J. Ass. Offic. Anal. Chem.
53(3), 499-508 (1970); Chem. Abs. _73_» 24179y (1970).
(274) "Phosphorimetric Determination of Some Pesticides Derived from
p-Nitrophenol", E. A. Martin, Can. J. Pharm. Sci. 5(1), 13-15
(1970); Chem. Abs. 21, 24173s (1970).
(275) "Effect of Ultraviolet Irradiation on the Thin-Layer Chromatography
of Insecticidal Phosphates and on Their Detection by the Benzo-
hydroxamic Acid Reaction", W. Ebing, J. Chromatogr. 46(2), 180-6
(1970); Chem. Abs. 21, 89161k (1970).
(276) "Spray Method for the Fluorescent Detection of Sulfur-Containing
Organic Compounds", P. E. Belliveau et al., J. Chromatogr. 48(3),
478-83 (1970); Chem. Abs. 21» 65306f (1970).
(277) "Detection, Separation, and Quantitative Recovery of Thirteen
Organophosphorus Pesticides on Silica Gel GF^e^ Thin-Layer
Chromatograms", D. C. Villeneuve et al., J. Chromatogr. 48(3),
567-71 (1970); Chem. Abs. 21» 54922c (1970).
(278) "Modified Enzymic Detection Method for Thin-Layer Chromatograms
of Pesticides", G. F. Ernst et al., J. Chromatogr. 49(2), 325-8
(1970); Chem. Abs. 21, 76024p (1970).
(279) "Effect of Liquid Phase Loading and Temperature on the Relative
Retentions in the Gas Chromatography of Methyl Parathion and
Parathion", P. S. Jaglan et al., J. Chromatogr. 50(3), 520-2
(1970); Chem. Abs. 21» 108641f (1970).
(280) "Design of a Polarographic Detector for High Speed, High Efficiency
Liquid Chromatography in Columns and Its Evaluation for the
Quantitative Analysis of Pesticides", J. G. Koen.et al., J.
Chromatogr. Sci. 8, 192-9 (April 1970); Chem. Abs. 21» 13437e (1970),
205
-------
(281) "Modifications to the Averell-Norris Method for the Determination
of Parathion Residues in Vegetables and Fruits", P. Wainstein et al.,
Rev. Fac. Cienc. Agr. Univ. Nac. Cuyo 16(1-2), 19-26 (1970); Chem.
Abs. 2Z» 99716n (1972).
(282) "Gas-Chromatographic Determination of Nitrostigmine (Parathion)
in Plasma Without Extraction", G. Boelcke, Arch. ToxLkol. 26(2),
161-8 (1970); Chem. Abs. _73, 65298e (1970).
(283) "Residue Analyses of Phosphorus-Containing Insecticides with a
Filter-Flame Photometer", H. Haub et al., Deut. Lebensm.-Rundsch.
66(10), 317-22 (1970); Chem. Abs. 21. 130055q (1970).
(284) "Separation and Identification of Farathion and Its Metabolites
in Autopsy Tissues by Thin-Layer Chromatography", S. N. Tewari
et al., Mikrochim. Acta (1), 58-60 (1970); Chem. Abs. 21, 131387r
(1970).
(285) 'tas-Chromatographic Analysis of Organophosphorus Pesticides", D. B.
Girenko et al., Gig. Sanit. 35(5), 77-9 (1970); Chem. Abs. 21,
65305e (1970).
(286) "Determination of Organophosphorus Compounds by Paper Chromatography
According to the Fluorescence Capacity in Ultraviolet Light",
R. V. Mishina, Metody Anal. Pestits. 67-71 (1970); Chem. Abs. 76.
42546g (1972).
(287) "0,0-Dimethyl 0-(Substituted-Phenyl)thiophosphates", R. Schelle
et al., Ger. (East) 70,871, 20 Jan 1970; Chem. Abs. 23, 76851f
(1970).
1971
(288) "Evaluation of Two Extraction Procedures for Pesticide Residues
Resulting from Foliar Application and Root Absorption", J. A.
Burke et al., J. Ass. Offie. Anal. Chem. 54(1), 142-6 (1971);
Chem. Abs. 2i» 75518m (1971).
(289) "Infrared and Ultraviolet Spectra of Seventy-Six Pesticides",
R. C. Gore et al., J. Ass. Offie. Anal. Chem. 54(5), 1040-82
(1971); Chem. Abs. 25, 117202g (1971).
(290) "Removal of Sulfur in Environmental Samples Prior to Gas Chromato-
graphic Analysis for Pesticide Residues", R. L. Schutzmann et al.,
J. Ass. Of fie. Anal. Chem. 54(5), 1117-19 (1971); Chem. Abs. 2§.»
75 7w (1972).
(291) "Negative Ion Mass Spectra of Some Pesticidal Compounds", P. C.
Rankin, J. Ass. Offie. Anal. Chem. 54(6), 1340-8 (1971); Chem.
Abs. 26, 69019z (1972).
206
-------
(292) "Cleanup of Pesticide and Polychlorinated Blphenyl Residues in Fish
Extracts by Gel Permeation Chromatography", D. L. Stalling et al.,
J. Ass. Offie. Anal. Chem. 55(1), 32-8 (1972); Chem. Abs. jte»
71128c (1972).
(293) "Routine Method for the Determination of Organophosphorus Insecti-
cides by Thin-Layer Chromatography", 0. Antoine et al., J. Chromatogr.
58(2), 247-56 (1971); Chem. Abs. .75, 75234m (1971).
(294) "Flavones as Fluorogenic Spray Reagents for Organothiophosphorus
Pesticides on Silica-Gel Layers", R. W. Frei et al., J. Chromatogr.
59(1), 135-40 (1971); Chem. Abs. .75, 109067b (1971).
(295) "Separation of Fifty Pesticides and Related Compounds and Poly-
chlorobiphenyls into Four Groups by Silica Gel", V. Leoni, J.
Chromatogr. 62(1), 63-71 (1971); Chem. Abs. _76, 82034v (1972).
(296) "Electrolytic Conductivity Detection of Some Nitrogen-Containing
Herbicides", W. P. Cochrane et al., J. Chromatogr. 63(2), 364-9
(1971); Chem. Abs. 7
-------
(304) "Thin-Layer Chromatographic Analysis of Organophosphate Pesticides
in the Study of Environmental Contamination (Italian Surface Waters)",
V. Leoni et al., Farmaco, Ed. Prat. 26(7), 383-93 (1971); Chem. Abs.
_75, 128757t (1971).
(305) "Analytical Studies on Pesticides and Related Compounds. VI.
Colorimetric Determination of S-Benzyl 0-Butyl S-Ethyl Phosphoro-
dithioate and Some Other Organophosphorus Pesticides", A. Murano
et al., Bunseki Kagaku 20(6), 665-72 (1971); Chem. Abs. _75, 97502z
(1971).
(306) "Esterase Inhibition Technique for the Detection of Organosphosphorus
Pesticides on Thin-Layer Chromatograms", T. Stijve et al., Mitt. Geb.
Lebensmittelunters. Hug. 62(1), 25-31 (1971); Chem. Abs. _75, 117195g
(1971).
(307) "Determination of Some Organophosphorus Insecticides in Animal
Tissues by Gas Chromatography", S. Vitorovic et al., Hrana Ishrana
12(9-10), 417-21 (1971); Chem. Abs. JT7, 43913g (1972).
(308) "Waste Water from the Pesticide Industry", V. Trifunovic et al.,
Zast. Mater. 19(10-11), 381-9 (1971); Chem. Abs. 2Z» 79232y (1972).
(309) "Catalytically Preparing Phosphate Esters", Kerr-McGee Corp., U. S.
3,607,991, 21 Sep 1971; Chem. Abs. 7S_, 129519d (1971).
1972
(310) "The p-Valve Approach to Quantitative Liquid-Liquid Extraction of
Pesticides From Water. I. Organophosphates. Choice of pH and
Solvent", I. H. Suffet et al., J. Agr. Food Chem. 20(1), 52-6
(1972); Chem. Abs. J76, 109005a (1972).
(311) "Metallofluorescent Indicators as Spray Reagents for the In Situ
Determination of Organophosphorus Pesticides on Thin-Layer
Chromatograms", T. F. Bidleman et al., Anal. Chim. Acta. 60(1),
13-23 (1972); Chem. Abs. 27, 84271q (1972).
(312) "Elution Solvent System for Florisil Column Cleanup in Organo-
chlorine Pesticide Residue Analyses", P. A. Mills et al., J. Ass.
Of fie. Anal. Chem. 55(1), 39-43 (1972); Chem. Abs. .76, 71131y (1972).
(313) "Infrared Analysis of Pesticide Formulations", S. W. Goza, J. Ass.
Off. Anal. Chem. 55(5), 913-17 (1972); Chem. Abs. Tl_% 160898s (1972).
(314) "Fluorometric Determination of Some Pesticides", M. E. Adonai,
Can. J. Pharm. Sci. 7(1), 21-2 (1972); Chem. Abs. 2Z» 15358m (1972).
(315) "Rapid Liquid Chromatography on Aluminum Oxide", D. Randau et al.,
J. Chromatogr. 66(2), 382-5 (1972); Chem. Abs. TT_, 31074w (1972).
(316) "Alkyl Phenyl Phosphates and Phosphoro(di)thioates", Stauffer Chemi-
cal Co., Ger. Offen. 2,162,344, 13 Jul 1972; Chem. Abs. TT_, 114023e
(1972).
208
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PENTACHLORONITROBEN2ENE
1956
1. "Separation and Identification of Chlorinated Organic Pesticides by
Chromatography", C. Mitchell, Assoc. Offie. Agr. Chemists 39, 484-9
(1956); Chemical Abs. 51, 2223h (1956).
1958
2. "Separation and Identification of Chlorinated Organic Pesticides by
Paper Chromatography", C. Mitchell, J. Assoc. Offie. Agr. Chemists 41,
781-816(1958); Chemical Abs 5.3, 2525b (1958).
1960
3. "Infrared Spectrophotometric Determination of Pentachloronitrobenzene
Residues", G. Paulig, Dent. Lebensm.-Rundschau 56, 296-8(1960); Chemical
Abs. .55, 13.747h (1961).
1961
4. "Separation and Analysis of Chlorobenzenes in Mixtures by gas
Chromatography", G. Nadeau, et al., Anal. Chem. 33, 1157-9(1961);
Chemical Abs. _56, 1982h (1961).
5. "Isolation of Insecticides and Fungicides by Gas Chromatography11,
G. Paulig, Deut. Lebensm.-Rundischau 57, 42-3(1961); Chemical Abs. 55,
10786b (1961).
6. "Determination of Pentachloronitrobenzene", S. Gorbach, Acta Chim. Acad.
Sci. Hung. 28, 199-206(1961); Chemical Abs. 5£, 6413d, (1961).
1962
7. "Investigations in the Use of the Microcoulometric Gas Chromatograph
for Pesticide Residue Analysis", J. Burke et al., J. Assoc. Offic. Agri.
Chemists 45, 348-54(1962); Chemical Abs. 57_, 2625 (1962).
8. "The Promising Utility of Infrared Assay of Pesticides and Their Residues",
C. Blinn, et al., SRI Pesticide Res. Bull. 2(4), 3-11(1962); Chemical
Abs. 60, 13811g (1962).
1963
9. "Infrared Spectra of Pesticides", W. Morris, Jr. et al., J. Assoc.
Office. Agr. Chemistry 46(6), 964-86(1963); Chejnical Abs. 60, 6157b
(1963).
10. "Sensitivity Tests for 22 Different Chlorinated Organic Pesticides
by Paper Chromatography", C. Mitchell et al., J. Assoc. Offic. Agr.
Chemists 46(6), 988-92(1963); Chemical Abs. 60, 6155 (1963).
209
-------
11. "Determination of Pentachloronitrobenzene in Dusts by Gas Chromatography",
J. Kanazawa, et al., Bunseki Kagaku 12(8), 758-60 (1963); Chemical Abs.
62, 2195g (1963).
12. "Polarographic Studies of Some Organic Compounds, XXI, A.C. and D.C.
Polarography of Pentachloronitrobenzene", H. Sato, Eisei Shikenjo
KenkyuHokoku No. 81, 8-10(1963); Chemical Abs. 62_, 14181 (1963).
1964
13. "Gas Chromatography Retention Times and Sensitivity Data for Insecticides
and Herbicides", J. Bonelli, et al., J. Agr. Food Chem. 12(4). 333-6
(1964); Chemical Abs. 61, 7635f (1964).
14. "Anal. Methods Pesticides, Plant Growth Regulators and Food Additives",
(G. Zewig, editor, Academic 2 127-136 (1964; Chem. Abs. 61, 11265b
(1964).
1965
15. "Extraction p-Values of Pesticides and Related Compounds in Six Binary
Solvent Systems", M. C. Bowman, et al., J. Aasoc. Offic. Agr. Chemicals
48(5), 943-52(1965); Chem. Abs. 64, 4l92h (1965).
16. "Colorimetric Determination of Small Amounts of Pentachloronitrobenzene",
S. Goto, et al., Buneski Kagaku 14(10), 921-6(1965); Chem. Abs. £8,
28706n (1968).
17. "Polarographic Determination of Pentachloronitrobenzene", N. Totir, et al.,
Rev. Chim. (Burharest) 16(10), 516 (1965);•Chem. Abs. 65, 11863e (1966).
1966
18. "Rapid Detection of Chlorinated Pesticide Residues by an Improved TLC
(Thin Layer Chromatography} Technique", M. F. Kovacs,Jr., J. Assoc.
Offic. Anal. Chemists 49(2), 365-70 (1966); Chem. Abs. 65, 2894e (1967).
19. "Gas Chromatogrphic Column for Pesticide Residue Analysis; Retention Times
and Response Data", J. A. Burke, et al., J, Assoc. Offic. Anal. Chemists
49(2), 374-85 (1966); Chem. Abs. 65, 2894e & g (1966).
20. "Thin-Layer Chromatography Identification of Pesticides Using Dip-Coated
Presensitized Microscopy Slides", N. V. Fehringer, et al., J. Chromatogr.
25(1), 95-101 (1966); Chem. Abs. 66, 18249k (1967).
21. "Electrochemical Methods for Quantitative Analysis of Pesticide Residues",
P. Nangniot, Meded. Rijksfac. Landbouwweitensch., Gent 1966, 31(3),
447-73; Chem. Abs. 69, 66430 (1968).
22. "Thin-Layer Chromatography of Pesticides", Z. Lebensm-Untersuch. - Forsch.
149-53 (1966); Chem. Abs. 64, 20546d (1966).
210
-------
23. "Residue Analysis of Agricultural Chemicals. III. Electron-Capture Gas
Chromatography of Various Pesticides", J. Kanazawa, et al., Nippon
Nogei Kagaku Kaishi 40(4), 178-84(1966); Chem. Abs. 65, 4571f (1966).
1967
24. "Determination of Terraclor in Crops and Soil by Electron-Capture Gas
Chromatography", T. P. Methratta, et al., J. Agr. Food Chem., 15(4),
648-50 (1967); Chem. Abs. 67, 64034t (1967).
25. "Pentachloronitrobenzene Residues in Potatoes", Gorbach et al., J. Agr.
Food Chem. 15(4), 654-6(1967); Chem. Abs. 67, 63034 (1967).
26. "Thin-Layer Chromatography of Isomeric Halo and Nitro Derivatives of
Aniline and Benzene", L. Fishbein, J. Chromatog. 27(2), 368-73(1967);
Chem. Abs., 67, 39932 (1967).
27. "Systematic Applications of Gas-Liquid Chromatography in Toxicology.
V. Pesticides and Evaluation of Toxic Levels", J. Jain et al.,
Microchem. J. 12(2), 265-72(1967); Chem. Abs. 67, 42137 (1967).
28. "Applicability of Aluminum Oxide in Simple Purification of Fat Exttacts
for Gas Chromatographic Analysis of Residual Chlorinated Insecticides",
E. Glofke, Pflanzenschutzberichte, 36(8-9-10), 143-55(1967); Chem.
Abs. 68, 77205 (1968).
1968
29. "Thin-Layer Chromatography; Relative Migration Data [RXDE! of Chlorinated
Pesticides", E. Thomas et al., J. Chromatogr. 1968, 25(1), 119-21;
Chem. Abs. £9, 18237 (1968).
30. "Testing of a Gas Chromatographic Method for Determination of Chlorinated
Insecticides in Butter, and Vegetable Products", F. Bro-Rasmussen et al.,
Z. Lebensm-Unters. Forsch, 1968, 138(5), 276-84; Chem. Abs. 29. 46234
(1969).
1969
31. "Alkaline Precolumn for Use in Gas-Chromatographic Pesticide Residue
Analysis", G. Miller et al., J. Ass. Offic. Anal. Chem. 1969, 52(3),
548-53; Chem. Abs. 21, 12014 (1969).
32. "Pesticide Residues. XIX. Determining Pesticide Residues in Natural Waters.
1. General Analytical Methods", R. Mestres et al., Ann. Fals. Expert.
Shim. 1969, 62(682), 75-85; Chem. Abs. 21, 34095 (1970).
1970
33. "Gas Chromatographic Separation of Mixed Chlorinated Fungicides", W.
Kilgore et al., J. Chromatogr. Sci. 1970,8(March), 166-8; Chem. Abs.
72, 131378 (1970).
211
-------
1971
34. "Infrared and Ultraviolet Spectra of Seventy-Six Pesticides", R. C.
Gore et al., J. Ass. Offic. Anal. Chem. 1971, 54(5), 1040-82; Chem.
Aba. 75, 117213 (1971).
35. "Mass Spectr of Fifteen Chlorinated Aromatic Fungicides", 0. Butzinger
et al., J. Ass. Offic. Anal. Chem. 1971, 54(1), 178-86; Chem. Abs.
74, 75516 (1971).
1972
36. "Fungicide Residues. I. Detection, Identification, and Determination
of Residues of(|Quintozene in Tomatoes, Lettuces, and Bananas by Gas
Chromatography, P. B. Baker et al., Analyst (London) 1972, 97(1154),
378-82; Chem. Abs. 27, 46776 (1972).
37. "Gas-Chromatographic Determination of Terraclor in Fertilizers", A. R.
Hanks et al., J. Ass. Off. Anal. Chem. 1972, 55(3), 657-9; Chem. Abs.
21, 57451 (1972).
38. "Rapid Screening Method for the Determination of Organochlorine Pesticide
Residues in Wheat by Electron Capture Gas Chromatography", I. Lev! et al.,
J. Ass. Off. Anal. Chem. 1972, 55(4), 794-9; Chem. Abs. 77, 73755 (1972).
212
-------
PRORATE
1952
1. "S-Alkoxymethyl 0,0'-dialkyl Dithiophosphates", American Cyanamid
Co., U. S. Patent 2,586,655, Feb. 19, 1952; Chemical Abs. 46,
8144e (1952).
1954
2. "Neutral Esters of Dithiophosphoric Acid", Farbenfabriken Bayer, A.-G.,
Ger. Patent 917,668, Sept. 8, 1954; Chemical Abs. 49, 12528i (1955).
1955
3. "Evaluation of 0,0'-dialkyl S-alkylthiomethyl Phosphorodithioates
as Systemic Insecticides", E. L. Clark et al., J. Agr. Food Chem.,
3, 834-6 (1955); Chemical Abs."50, 44461 (1956).
1956
4. "Dialkyl Alkylmercaptoalkyl Dithiophosphates", Farbenfabriken.Bayer,
A.-G., U. S. Patent 2,759,010, August 14, 1956; Chemical Abs, .51,
2849h (1957).
5, "Neutral Thionothiolphosphoric Esters", Farbenfabriken Bayer, A.-G.,
Ger. Patent 947,369, Aug. 16, 1956; Chemical Abs. 51, 4425e (1957).
1957
6. "Metabolism of the Systemic Insecticide 0,0-diethyl S-ethylthiomethyl-
phosphorodithioate (Thimet) in Plants", J. S. Bowman et al., J. Agr.
Food Chem.5, 192-7 (1957); Chemical Abs. 51, 17061h (1957).
7. "Color Reaction of 2,6-Dibromo-N-Chloro-p-Benzoquinone Inline with
Thiophosphate Insectides on Paper Chromatograms", J. J. Menn, et al.,
J. Agr. Food Chem. 5, 601-2 (1957); Chemical Abs. 51, 16989h (1957).
8. "Hydrolysis of the Phosphoric Acid Ester Insectide", R. Muhlmann and
G. Schrader, Z. Naturforsch,12b,196.208 (1957).Chemical Abs..51,99951 (1957).
1959
9. "Conversion of Some Organophosphate Pesticides to Less Polar Compounds
by Ultraviolet Light", J. W. Cook et al., J. Assoc. Offie. Agri. Chemists
41, 211-12'(1959); Chemical Abs. 53, 9555 (1959).
10. "Microdetermination, of Parathion (and Related Compounds", Yu-Shih
Chem, Bull. Assoc. Agr. Chem. Nat'l. Taiwan Univ. (Formosa) 8, 21-4 (1959);
Chemical Abs. 53, 227071 (1959).
11. "Organophosphorus Compounds 'I. 0,0-Dialkyl S-Alkyl for Substituted
Alkylthio (or oxy)methyl) (or Substituted Methyl) Phosphorodithionate",
Shir-Hsien Yang, et al, Hua Hsueh Pao 25, 402-8 (1959); Chemical Abs.
54, 19467i (1960).
213
-------
1960
12. "Colorlmetric Determination of Residues of Phorate and Its Insectlcldally
Active Metabolites", P. A. Giang et al., Food Chem. 8, 51-4 (1960);
Chemical Abs. 55 3913e (1961).
1961
13. "The Determination of Organophosphorus Insectides In Vegetables: A
General Method for Insectide Residues11, E. Q. Laws, et al., Analyst
86, 249-55 (1961); Chemical Abs. 55, 20257f (1961).
14. Chromatographic Identification of Some Organophosphate InsectIdes",
H. F. MacRae, et al., J. Assoc. Offie. Agr. Chemists, 44, 207-11 (1961);
Chemical Abs. 55, 202961 (1961).
1962
15. "Application of Oscillographic Polarography to Determination of
Organic Phosphorus Pesticide Residues", J. Assoc. Offic. Agr. Chemists,
45, 401-6 (1962); Chemical Abs. 57, 3820h (1962).
16. "Electron Capture with an Argon lonization Detector in Gas Chromato-
graphic Analysis of Insecticides", A. D. Moore, J. Econ. Entomol. 55,
271-2 (1962); Chemical Abs. 57, 7676b (1962).
17. "Nuclear Magnetic Resonance Study of Organophosphorus Compounds",
G. Mavel et al., Compt. Rend. 254, 260-2 (1962); Chemical Abs. 56,
9602c (1962).
1963
18. "Thin-Layer Chromatography for Insectide Analysis", C. Walker et al.,
J. Assoc. Offic. Agr. Chemists 46, 250-61 (1963); Chemical Aba. 58.
14626g (1963).
19. "Thin-Layer Chromatographic Isolation and Infrared or Colorimetric
Identification of Thimet Residues", R. C. Blinn, J. Assoc. Offic.
Agr. Chemists 46 (6), 952-60 (1963); Chemical Abs. 60, 4690c (1964).
20. "Residue Analysis of Phorate by Cholinesterase Inhibition After
Oxidation", T. E. Archer, et al., J. Agr. Food Chem. 11, 58-63 (1963);
Chemical Abs. 58, 4967d (1963).
21. "Application of the Microcoulometric Titrating System as a Detector in
Gas Chromatography of Pesticide Residues", J. A. Challacombe, et al.,
Residue Rev. 57-72 (1963); Chemical Abs. .61, 9975h (1964).
•
22. The Detection of Organophosphorus Pesticides on Thin-Layer Chromatograns",
P. J. Bunyan, Analyst 89 (1062), 615-18 (1964); Chemical Abs. 61,
15282f (1961).
214
-------
1964
23. "Gas Chromatography Retention Times and Sensitivity Data for
Insecticides and Herbicides", E. J. Bonelli, et al., J. Agr. Food
Chem. 12 (4), 333-6 (1964); Chemical Abs. 61, 7635f (1964).
24. "Cryoscopic Analysis of Organic Phosphate Pesticides; Kalathion,
Dimethoate, 0,0-Diethyl 0-(2-Pyrazinyl) Phosphorothionate, and
Phorate", R. J. Best et al., J. Agr. Food Chem. 12(6), 546-9 (1964);
Chemical Abs. 62 lOOld (1965).
25. "The Oxidative Conversion of Thimet to its Oxygen Analog Sulfone",
R. C. Blinn, J. Assoc. Offie. Agr. Chemists 47(4), 641-5(1964);
Chemical Abs. .61, 15258d (1964).
26. "Thin-Layer Chromatography of Organophosphorus Pesticides and
Acids on Microchromatoplates", C. W. Stanley, J. Chroma tog. 16(3),
467-75 (1964); Chemical Abs. 62, 11090a (1965).
27. "Changes in Official Methods Analysis Made at the Seventy-Seventh
Annual Meeting October 14-17, 1963", Anon. J. Assoc. Offie. Agr.
Chemists 47(1), 170-202(1964); Chemical Abs. 60, 13537h, (1964).
28. "Collaborative Study of Infrared Methods for Phorate in (Insecticidel)
Formulations", N. R. Pasarela, J. Assoc. Offie. Agr. Chemists 47(2),
245-7 (1964); Chemical Abs. 61, 2417b (1964).
29. "Thimet" G. L. Sutherland et al., Anal. Methods Pesticides, Plant
Growth Regulators and Food Additives", G. Zweig, Editor, Adademic,
2t 487-505 (1964); Chemical Abs. 61, 11264g (1965).
1965
30. "Simultaneous and Selective Detection of Phosphous, Sulfur, and
Halogen in Pesticides by Microcoulometric Gas Chromatography",
H. P. Burchfield, J. Agr. Food Chem. 13 (6), 511-16 (1965); Chemical
Abs. 64, 4193b (1966).
31. "Colorimetric Method for Determining Residues of Thimet (Phorate)",
G. Winnett, et al., J. Assoc. Offic. Agr. Chemists 48 (2), 370-3
(1965); Chemical Abs. 63,(1146d (1965).
32. "Extraction p-Values of Pesticides and Related Compounds in Six
Binary Solvent Systems", C. Bowman, et al., J. Assoc. Offic. Agr.
Chemists 48 (5), 943-52 (1965); Chemical Abs. 64, 4192h (1966).
33. "Selective Detection of Phosphorus, Sulfur, and Halogen Compounds
in the Gas Chromatography of Drugs and Pesticides", H. P. Burchfield,
et al., J. Gas. Chromatog. 3 (1), 28-34 (1965); Chemical Abs. 62.
11629e (1965).
34. "Gas-Liquid Chromatography of Organophosphorus Pesticides" J. Kanazawa,
et al., Agr. Biol. Chem. (Tokyo) 29 (1), 56-60 (1965); Chemical Abs.
62, 12385a, (1965).
215
-------
1966
35. "Low Pressure Emission Spectrometric Determination of Parts Per
Billion residue Levels of Phosphorus Insecticides", C. Bache,
et al., Anal. Chem. 38(12), 1757-8(1966); Chem. Abs. 66, 1817J
(1967).
36. 'Gas Chromatographic Column for Pesticide Residue Analysis; Retention
Times and Response Data", J. A. Burke, et al., J. Assoc. Offie.
Anal. Chemists 49(2), 374-85(1966); Chem. Abs. 65, 2894g (1966).
37. "Separation and Detection of Submicrogram Quantities of Pesticides
by an Improved TLC Technique, H. Beckman, et al., Bull. Environ.
Contam. Toxicol. 1(3), 78-85(1966); Chem. Abs. 65, 7894e (1966).
38. "Phosphorus Detector for Pesticides Analysis", C. Hartmann, Bull.
Environ. Contam. Toxicol. 1(4) 159-68(1966); Chem. Abs. 65 17623e
(1966).
i
39. "Determination of Organophosphorus Insecticide Residues Using Cooke's
Emission Spectroscopic Detector", C. A. Bache, et al., Residue Rev.
12, 35-44(1966); Chem. Abs. 65 7895e (1966).
40. "0,0-Dialkyl S-Alkylthiomethyl Dithiophosphates", Hokko Chemical
Industry Co., Ltd., Japan 11,859(1966), June; Chem. Abs. 65. 15231a
(1966).
41. "0,0-Dialkyl S-Alkylthiomethyl Dithiophosphates", Hokko Chemical
Industry Co., Ltd, Japan 11,860(1966), June; Chem. Abs. 65. 15231b
(1966).
1967
42. "Direct Fluorescent Detection of Organothiophosphorus Pesticide*
and Some of Their Sulfur-Containing Breakdown Products After Thin-
Layer Chromatography", M. H. Ragab, J. Ass. Offic. Anal. Chem.50)5),
1088-98(1967); Chem. Abs. 67, 99119p (1967).
43. "The Gas-Chromatographic Examination of Organophosphorus Pesticides
and Their Oxidation Products", J. Ruzicka, et al., J. Chromatogr.30
(1),92-9(1967); Chem. Abs. 68. 21155y (1968).
44. "The Gas-Chromatographic Determination of Organophosphorus Pesticides.
II. A Comparative Study of Hydrolysis Rates", J. H. Ruzicka, et al.,
J. Chromatogr. 31(1), 37-47(1967); Chem. Abs. 68, 2191r (1968).
45. "Modified Hydrogen Flame-lonization Detector, Highly Sensitive and
Selective for Phosphates", R. V. Hoffman, Lect. Gas Chromatogr. 1966-
1967. 137-47, Edited by L. R. Mattick, Plenum Press; New York, N. Y.;
Chem. Abs. 70, 95709v (1969).
216
-------
46. "Systematic Applications of Gas-Liquid Chromatography in Toxicolocy.
V. Pesticides and Evaluation of Toxic Levels", N. C. Jain, et al.t
Microchem. J. 12(2), 265-72(1967) of preceding abstrs.; Chem. Abs.
67, 42144p (1967).
47. "Thin-Layer Chromatographic Separation Scheme for Insecticidally
Active Phosphoric Acid Esters", J. A. Guth, Pflanzenschutzberichte
35(9-10), 129-43(1967); Chem. Abs. £7, 72784q (1967).
48. "Thiophosphates", American Cyanamid Co. U. S. Patene 3,309,432,
March 14, 1967; Chem. Abs. ,66, 114911r (1967).
1967
49. "Alkyl ThiomethyIdithiophosphate", Hokko Chemical Industry Co., Ltd.,
Japan 1743(1967), Jan. 26; Chem. Abs. 66 , 85467t (1967).
50. "Alkyl Thiomethy1 Dithiophosphates", Bokko Chemical Industry Co.,
Ltd., Japan 4455(1967), Feb. 23.; Chem. Abs. 67, 11205e (1967).
1968
51. "Automated Analysis of Organophosphorus Insecticides by Wet Digestion-
Oxidation and Colorimetric Determination of the Derived Orthophosphate",
E. Ott, et al., J. Ass. Offic. Anal. Chem. 1968, 51(3) 697-708;
Chem. Abs. 69, 9901b (1968).
52. "High-Resolution N.M.R. Spectra of Pesticides. I. Organophosphorus
Pesticides1.1, L. H. Keith, et al., J. Ass. Offic. Anal. Chem. 1968,
51(5), 1063-94; Chem. Abs. 69, 75849s (1968).
53. "Thin-Layer Chromatography of Organophosphorus Insecticides with
Several Adsorbents and Ternary Solvent Systems", M. E. Getz, et al.,
J. Ass. Offic. Anal. Chem. 1968, 51(5), 1101-7; Chem. Abs. 69,
75850k (1968).
54. "Versatility of OV-17 Substrate forGas Chromatography of Pesticides",
C. A. Bache, et al., J. Ass. Offic. Anal. Chem. 1968, 51(6), 1270-1;
Chem. Abs. 70, 27907h (1969).
55. "Microwave-Powered Emission Determination of Residues of Organic
Bromine, Chlorine, Iodine, Phosphorus, and Sulfur Pesticides in a
Helium Plasma", C. A. Bache, et al, Biomed. Appl. Gas Chromatogr.
1968, 2, 165-78; Chem. Abs. 73, 76019r (1970).
56. "The Chromatographic Determination of Organophosphorus Pesticides.
III. The Effect of Irradiation on the Parent Compounds", T. H.
Mitchell, et al., J. Chromatogr. 32(1), 17-23(1968); Chem. Abs.
68, 67980s (1968).
217
-------
57. "Nuclear-Magnetic Resonance Studies of Phosphorus(V) Pesticides.I",
H. Bated, et al., Anal Cham. Acta 41(2), 259-68(1968); Chain. Abs.
68, 77181w (1968).
58. "Use of an Electron-Capture Detector In Gas Chromatography. III.
Example of its Application. Study of the Response of Some Chlorinated
and Phosphorylated Pesticides", P. Devaux, et al., Bull. Soc. Chin.
Fr. 1968, (4), 1627-33; Chen. Abs. 69, 26229f (1969).
1969
59. "Pesticides Residues. Recovery of 65 Organophosphorus Pesticides from
Florisil with a New Solvent-Elution System", H. Beckman, et al.,
J. Ass. Offie. Anal. Cham. 1969, 52(2), 286-93; Chen. Abs. 22
86520z (1969).
60. "Gas Chromatography of Organophosphorus Pesticides;Retention Times
and Response Data on Three Columns", R. R. Watts, et al., J. Ass.
Offie. Anal. Chem. 1969, 52(3), 513-21; Cham. Abs. 21 12019s (1969).
61. "Supplementary Interpretations of the N.M.R. Spectra of Phosphorus
Pesticides", L. H. Keith, et al., Anal. Chim. Acta 1969, 44(2),
447-8; Chem. Abs. 23 76682q (1969).
62. "Identification of Organophosphate Pesticides by Gas Chromatography
With the Flame Photometric Detector", W. Stanley, et al., J. Chromatogr.
1969, 40(2), 289-93; Chem. Abs. 10, 114094J (1969).
63. "Gas-Liquid and Thin-Layer Chromatography of Phorate, Disulfoton, and
Five of Their Oxidation Products", D. L. Grant, et al., J. Chromatogr.
1969, 44(1), 67-74; Chem. Abs. 12, 11586h (1970).
64. "Thin-Layer Chromatographic-Encymic Detection of Organophosphorus
Insecticides. Thin-Layer Chromatographic Behavior of Some Other
Insecticides", H. Ackerman, J. Chromatogr. 1969, 44(2), 414-18;
Chem. Abs. 22• 77910r (1970).
65. "Chromatographic Determination of Trace Amounts of Pesticide Residues",
M. Beroza, et al., Trace Subst. Environ. Health-3, Proc. Univ. Mo.
Annu. Conf., 3rd 1969, 331-51", Chem. Aba. 74, 2963t (1971).
66. "Determination of Organophosphorus Pesticides in Water", G. Zweig,
Residue Rev. 1969, 26, 17-36; Cham. Abs. 2i> 80107u (1969).
67. "Deodorizing 0,0-Dialkyl S-(alkylthio)alkyl Phosphorodithioates",
American Cyanamid Co., U. S. Patent 3,439,071, April 15, 1969;
Chem. Abs. 21* 49258v (1969).
218
-------
1970
68. "GLC (Gas-Liquid Chroma tographic) Retention Tina* of Pesticides and
Metabolites Containing Phosphorus and Sulfur on Fouv Thermally
Stable Columns", M. C. Bowman, at al., J. Ass. Offic. Anal. Cham. ,
1970, 53(3), 499-508; Ch«n. Abs. 73, 24179y (1970).
69. "Effect of Ultraviolet Irradiation on the Thin-Layer Chromatography
of Insecticidal Phosphates and on Their Detection by the Bencohydroxamic
Acid Reaction", W. Ebing, J. Chromatogr. 1970, 46(2), 180-6; Chen.
Abs. 22, 89161k (1970).
70. "Detection, Separation, and Quantitative Recovery of Thirteen
Organophosphorus Pesticides on Silica Gel GF254» Thin-Layer
Chroma to grams", D. C. Villenuve, et al., J. Chromatogr. 1970, 48
(3), 567-71; Chem. Abs. .73, 54922c (1970).
71. "Modified Enzymic Detection Method for Thin-Layer Chromatograms of
Pesticides", G. F. Ernst, et al., J. Chromatogr. 1970, 49(2), 325-8;
Chem. Abs. 21* 76024p (1970).
72. "Polarography of Demeton, Disulfoton, and Phorate", 1. J. Graham-Bryce ,
Pestic. Sci. 1970, 1(2), 73-4; Chem. Abs. j£, 13441b (1970).
73. "Residue Analyses of Phosphorus -Containing Insecticides with a Filter-
Flame Photometer", H. Haub, et al., Deut. Lebansm.-Rundsch, 1970,
66(10), 317-22; Chem. Abs. 23, 130055q (1970).
1971
74. "Routine Method for the Determination of Organophosphorus Insecticides
by Thin-Layer Chromatography11, 0. Antoine, J. Chromatogr. 1971, 58(2),
247-56; Chem. Abs. 21, 75234m (1971).
75. "Method for Confirmation of Organophosphorus Compounds at the Residue
Level", T. M. Shafik, et al., Bull. Environ. Contain. Toxicol. 1971,
6(1), 55-66; Chem. Abs. 2&» 124014e (1971).
76. "Thin-Layer Chromatographic Analysis of Organophosphate Pesticides in
The Study of Environmental Contamination (Italian Surface Waters)",
V. Leoni, et al., Farmaco, Ed. Prat. 1971, 26(7), 383 -93 w, Chem. Abs.
, 128757t (1971).
1972
77. "Infrared Analysis of Pesticide Formulations'1, S. W. Goca, J. Ass.
Off. Anal. Chem. 1972, 55(5), 913-17; Chem. Abs. 22. 160898s (1972).
78. "pH -Sensitive Fluorogenic Spray Reagents. II. Quantitative Studies
with Pesticides", R. W. Frei, et al., Chromatographia 1972, 5(5)
296-300; Chem. Abs. 22* 84268u (1972).
219
-------
79, "Metallofluorescent Indicators as Spray Reagents for the in situ
Determination of Organophosphorus Pesticides on Thin-Layer Chromatogr.
T. F. Bidleman et al., Anal. Chlm. Acta 1972, 60(1), 13-23; Chem.
Abs. 77, 84271q (1972).
80. "Chemical Hydrolysis of Some Organic Phosphorus and Carbamate Pesticic
in Aquatic Environments", S. D. Faust, et al., Environ.. Lett. 1972,
3(3), 171-201; Chem. Abs. 22» 110352p (1972).
220
-------
SIMAZINE
1945
(1) "Arsenic Derivatives of Phenoxy-s-triazines", I. H. Witt, et al.,
J. Am. Chem. Soc. 67, 1078-9 (1945); Chem. Abs. 39, 40783 (1945).
1948
(2) "Substituted Chlorodiamino-s-triazines", W. M. Pearlman, et al.,
J. Am. Chem. Soc. ,70, 3726-8 (1948); Chem. Abs. 43_, 1425i (1949).
1951
(3) "Cyanuric Acid Derivatives. I. Aminochloro-s-triazines", T. Thurston,
et al., J. Am. Chem. Soc. 73, 2981-3 (1951); Chem. Abs. 46, 997£
(1952).
1956
(4) "Further Phytotoxic Triazines", A. Cast, et al., Experientia 12,
146-8 (1956); Chem. Abs. 50, 11595f (1956).
1958
(5) "Triazine Weed Killers", J. R. Geigy Akt.-Ges, Swiss 329,277, June
14, 1958; Chem. Abs. 54, 20061h (1960).
1960
(6) Synthesis of 2,4-bis(ethylamino)-6-chloro-s-triazine", 6. Matolesy,
et al., Zhur. Prilkad. Khim. 33, 1224-6 (1960); Chem. Abs. 54,
21124a (1960).
1960
(7) "2,4-Bis(ethylamino)-6-chlorotriazine", U.S.S.R. 129,769, July 1, 1960;
Chem. Abs. J>5, 4551h (1961).
1960
(8) "Diaminochloro-s-triazines For Use as Herbicides and Plant-growth In-
hibitors", J. R. Geigy Akt.-Ges., Swiss 342,784-5, Jam. 15, 1960; Chem.
Abs. 55, 5552b (1961).
221
-------
1961
(9) "The Effect of Ultraviolet Light (2537 A.) on 141 Pesticide Chemicals
by Paper Chromatography", L. C. Mitchell, J. Assoc. Offie. Agr. Chem-
ists 44, 643-712 (1961); Chem. Abs. 56_, 3849e (1962).
1961
(10) "Potential Herbicides", N. N. Mel'nikov, et al., Khim. Prom. 1961.
703-4; Chem. Abs. 58, 526b (1963).
1962
(11) "Procedure For Estimating Residual Amounts of Simazine in Corn Grain",
G. P. Vavilina, et al., Vopr. Pitaniya 21, No. 4, 60-3 (1962); Chem.
Abs. 57_, 12946i (1962).
1962
(12) "Detection of Traces of Some Triazine Herbicides by Gas-liquid Chroma-
tography", E. D. Chilwell, et al., J. Sci. Food Agr. 13, 425-7 (1962);
Chem. Abs. _57, 14224a (1962).
1962
(13) "Determination of Small Quantities of Atrazine and Simazine in Corn
by Paper Chromatography", A. Major, Jr., J. Assoc. Offie. Agr. Chem-
ists 45, 679-82 (1962); Chem. Abs. 57., 14240b (1962)*
(14) "Aminochlorotriazine Derivatives", Nehezvegyipari Kutato Intezet,
et al., Hung. 149,189, Mar. 31, 1962; Chem. Abs. 58, 13972b (1963).
(15) "Behavior of Certain Substituted s-Triazines, in Connection with the
Synthesis of Herbicides", A. Velnice-Riu, et al., Rev. Chim.
(Bucharest) 13, 513-16 (1962); Chem. Abs. 59, SOOOe (1964).
(16) "Determination of Small Concentrations of Herbicide Simazine
2-chloro-4,6- bis(ethylamino)triazine. L. I. Gavrilova, Gigiena i
Toksikol, Novykh Pestitsidov 1 Klinika Otravlenii, Dokl, 2-oi
Vtoroi Vses. Konf. 1962. 112-13; Chem. Abs. 60, 8569a (1964).
1963 " ' ' "
(17) "Two Years' Experience in Chemical Weed Control with Hungazin
Preparations", G. Ubrizsy, et al., Kiserl. Kozlemen., A. Novenyter-
mesz. 56(2), 3-19 (1963); Chem. Abs. 61, 138l4g (1964).
(18) "Volatility of Various Herbicides Under Laboratory Conditions",
C. L. Foy, Res. Progr. Rept. Western Weed Control Conf. 1963. 81-2;
Chem. Abs. 64, 1279h (1966).
222
-------
1964
(19) "Photodecomposition of Triazines", L. S. Jordan, et al., Weeds
12(1), 5-6 (1964); Chem. Abe. 60, 11302f (1964).
(20) "Analysis of Triazine Herbicides", K. Stanmbach, et al., Weed
Res. 4(1), 64-74 (1964; Chem. Abs. 60, 13811b (1964).
(21) "Thin-Layer Chromatography of Herbicidal Compounds", H. 6. Henkel,
et al., J. Chromatog. 14(2), 283-5 (1964); Chem. Abs. 61, 24llg
(1964).
(22) "Thin-Layer Chromatographic Behavior of Compounds Effective as
Herbicides", H. 6. Henkel, Chimia (Aarau) 18(7), 252-4 (1964);
Chem. Abs. 61, 8828d (1964).
(23) "The Determination of Some Triazine Herbicides by Liquid Chro-
matography with Particular Reference to Atraton in Soil",
C. A. Benfield, et al., Analyst £9(1060), 475-9 (1964); Chem.
Abs. (61, 9971d (1964).
(24) "New Triazines as Plant Growth Inhibitors", J. R. Geigy A.-G.,
Swiss 375,730, Apr. 30, 1964; Chem. Abs. 61, 10692h (1964).
(25) ll2-Chloro-4-isopropylamino-6-ethylamino-s-triazine", Czech.
110,352, Mar. 15, 1964; Chem. Abs. £1, 12017e (1964).
(26) "The Gas Chromatography of Triazine Herbicides", H. G. Henkel,
et al., J. Gas Chromatog. 2(7), 215-18 (1964); Chem. Abs. 61,
12560f (1964).
(27) "Penetration of and Persistence on the Soil of the Herbicide
Atrazine", L. A. Birk, et al., Can. J. Plant Sci. 44(1), 21-7
(1964); Chem. Abs. 61, 13814c (1964).
(28)
"Simazine", E. Knuesli, Anal. Methods Pesticides, Plant Growth Regulators,
Food Additives (Gunter Zweig, editor, Academic) 4, 213-33 (1964);
Chem Abs. 62, 4819f (1965).
(29) "Herbicides", B. J. Heywood. Rept. Progr. Appl. Chem. (H. S.
Rooke, editor), £9, 357-64 (1964); Chem. Abs. 64, 1279g (1966).
1965
(30) "Use of Microcoulometric Gas Chromatograph for Triazine Herbi-
cides", A. M. Mattson, et al., J. Agr. Food Chem. .13(2), 120-2
(1965); Chem. Abs. 62, 12369d (1965).
223
-------
(31) "Gas-Liquid Chromatography of Organic Herbicides", J. Kanazawa,
Bunseki Kagaku .14(5), 481-3 (1965); Chem. Abs. 63, 4878g (1965).
(32) "The Thin-Layer Chromatographic Determination of Triazine Her-
bicides in Soil and Water", D. C. Abbott, et al., Analyst 90
(1071), 356-61 (1965); Chem. Abs. 63, 6253b (1965).
(33) "Quantitative Determination of Atrazine, Simazine, and Propa-
zine by Infrared Absorption Spectra. V. I. Yakutin, et al.,
Zavodsk. Lab. .31(5), 564-6 (1965); Chem. Abs. 63, 7589g (1965).
(34) "Determination of s-Triazine Derivatives. I. Determination of
Chlorotriazines in the Presence of Each Other", L. Legradi,
et al., Magy. Kern. Folyoirat 21(7), 304-6 (1965); Chem. Abs.
63, 12321b (1965).
(35) "II. Detection of Chlorotriazines in the Presence of Each Other",
L. Legradi. Ibid. 306-9; Chem. Abs. 63, 12321d (1965).
(36) "Determination of Small Quantities of Simazine and Atrazine
in Soil", E. Grou. Rev. Chim. (Bucharest) 16(7), 316-17 (1965);
Chem. Abs. 64, 1295d (1966).
(37) "2,4-Bis(ethylamino)-6-chlorotriazine (Simazine)'. U.S.S.R.
154,282, July 7, 1965; Chem. Abs. 64, 21l4e (1966).
(38) "Determination of Simazine in the Air", A. A. Russkikh,
Gigiena i Toksikol. Pestitsidov i Klinika Otravlenii, Sb. (Kiev:
Zdorov'e) 1965. 580-1; Chem. Abs. 65, 17591g (1966).
(39) "Infrared Spectroscopy of Triazine-Base Herbicides", J. Jorg,
et al., Pflanzenschutz Ber. 32. 129-45 (1965); Chem. Abs. 65.
19239b (1966).
1966
(40) "Determination of Some s-Triazine Herbicides by Thin-Layer
Chromatography", L. P. Manner, J. Chromatog. .21(3), 430-8 (1966);
Chem. Abs. 64, I4882b (1966).
(41) "Analysis of Several Vegetables for Residues of Trifluralin,
Prometryne, or Prometryne Plus Atrazine", T. W. Kerr, et al.,
Proc. Northeast Weed Control Conf. 20. 106-8 (1966); Chem.
Abs. 64, 18300e (1966).
224
-------
(42) "Gas Chromatographic Column for Pesticide Residue Analysis;
Retention Times and Response Data", J. A. Burke, et al., J. Assoc.
Offie. Anal. Chemists 49(2), 374-85 (1966); Chem. Abs. 65, 2894g
(1966).
(43) "Selective Detection of Nitrogen Compounds in Electrolytic Con-
ducitivity Gas Chromatography", D. M. Coulson, J. Gas. Chromatog.
4(8), 285-7 (1966); Chem. Abs. 65, 14429d (1966).
(44) "Spectrophotometric Determination of Small Amounts of Triazine
Herbicides (Simazine, Atrazine, Propazine, and Chlorazine) in
Plant Tissues", A. A. Petunova, et al., Metody Opred. Regul.
Rosta Gerbits., Akad. Nauk SSSR, Inst. Fiziol. Rast. 1966.
139-49; Chem. ABs. 67, 42808h (1967).
(45) "Determination of Simazine, Propazine, and Atrazine in the Soil",
P. Neubert, et al., Arch. Pflanzenschutz 2(3), 179-94 (1966);
Chem. Abs. 68, 21096e (1968). ~
i ~"~
1967
(46) "Gas-Chromatographic Investigation of Aminochlorotriazines",
J. Lukacs, et al., Magy. Kern. Foly. 73(6), 289-91 (1967); Chem.
Abs. 67, 42807g (1967).
(47) "Determination of Traces of Chlorinated Pesticides (Dichloralurea,
Sodium Trichloroacetate, Simazine, Propazine, and Dichloro-
diphenyltrichloroethane) in Biological Substrates", M. I.
Gzhegotskii, et al,., Lab. Delo 1967(5). 303; Chem. Abs. .67,
42870x (1967).
(48) "Infrared Absorption Spectra and Polymeric Structures of Three
s-Triazine Herbicides and Their Metabolites", J. Y. T. Chen,
J. Assoc. Offie. Anal. Chem. 50(3), 595-600 (1967); Chem. Abs.
67, 63556q (1967).
(49) "The Identification and Determination of Various Triazine
Herbicides in Biological Materials", R. Delley, et al., Fresenius1
Z. Anal. Chem. 228(1), 23-38 (1967); Chem. Abs. .67, 81380g (1967).
1968
(50) "Color linetrie Methods for the Determination of Simazine and Re-
lated Chloro-s-triazines", M. T. H. Ragab, et al., J. Agr. Food
Chem. .16(2), 284-9 (1968); Chem. Abs. 68, 76986a (1968).
225
-------
1967
(51) "Concomitant Determination of Alkylamino Triazines", K. Jeney,
Kiserl. Kozlem., A. Kotet 1967, 60(1-3), 57-62; Chem. Abs. 21*
2336d (1969).
(52) "Determination of Simazine and Monuron in Soil, Citrus Fruits,
Grape Juice, and Tea Leaves", A. A. Gigineishvili, Mater. Sess.
Zakavkaz. Sov. Koord. Nauch.-Issled. Rab. Zashch. Rast. 1967
(Pub. 1968), 555-6; Chem. Abs. J3, 119443u (1970).
1968
(53) "Improved GLC ("Gas-Liquid Chromatography)Uethod for s-Triazine
Residue Determination", R. C. Tindle, et al., J. Assoc. Offic.
Anal. Chem. 1968. 51(3), 682-8; Chem. Abs. 69, 26088j (1968).
(54) "2-Chloro-4,6-bis(alkylamino)-s-triazines", J. R., Geigy, A.-G.,
U.S. 3,376,302, Apr. 2, 1968; Chem. Abs. 69, 59290x (1968).
(55) "Electrochemical Purification of Cyanide-Containing Waste Waters",
Ail-Union Scientific-Research Institute for Water Supply, Sewage
Systems, and Hydraulic Installations) U.S.S.R. 234,245, Dec. 24,
1968; Chem. Abs. 70, 117922? (1969).
1969
(56) "Determination of Cyanogen Chloride, Hydrogen Cyanide, Cyanuric
Chloride, and Simazine in the Air", A. A. Belyakov, et al.,
Gig. Sanit. 1969,-34(8), 54-7; Chem. Abs. TL> 104905f (1969).
(57) "The Atmosphere in Plants for Production of Cyanuric Cyloride
and Simazine", A. A. Russkikh, Nov. Obi. From.-Sanit. Khim.
1969. 112-17; Chem. Abs. £1, H6268p (1969).
(58) "Analysis of Herbicide Mixtures Containing Simazine, 2,4-D,
and TCA (Trichloroacetic Acid), P. Fusi, et al., Ann. Chim. (Rome)
1969. 59(8-9), 756-61; Chem. Abs. 72, 4l983c (1970).
(59) "Herbicidal 2-chloro-4,6-disubstituted-amino-s-triazines", J. R.
Geigy, A.-G., Fr. 1,562,266, Apr. 4, 1969; Chem. Abs. 72, 55457w
(1970).
*
(60) "Preparation of (2HChloro-4,6-di(alkylamino)-8-triazines",
• J. R. Geigy, A.-G. Rom. 52,054, Nov. 18, 1969; Chem. Abs. 73,
66628z (1970).
226
-------
(61) "Determination of Simazine and Monuron Residues in the Soil",
A. A. Gigineishvili, Tr. Inst. Zashch. Rast., Tiflis 1969.-21.
323-7; Chem. Abs. 25, 34287n (1971).
(62) "Determination of Some Triazine Group Herbicides in the Air",
S. I. Trofimova, Gig. Primen., Toksikol. Pestits. Klin. Otravl.
1969. No. 7, 636-40; Chem. Abs. H, 122728h (1972).
1970
(63) "Carcinogenic Properties of s-Triazine Derivatives", G. B. Pliss,
et al., Vop. Onkol. 1970.-16(1). 82-5; Chem. Abs. 72, 99452v
(1970).
(64) "Photochemistry of Bioactive Compounds. Photochemistry of
Selected 2-chloro- and 2-methylthio-4,6-di(alkylamino)-s-triazine
Herbicides", B. E. Pape, J. Agr. Food Chem. 1970. 18^2), 202-7;
Chem. Abs. 22, HOlllf (1970).
(65) "Mass Spectra of Chloro-, Aminochloro-, and Ethyl-aminochloro-s-
triazines", J. A. Ross, Org. Mass Spectrom., 1970. 3(2), 219-29;
Chem. Abs. 72, 115863n (1970).
(66) "Spectrophotometric Determination of Simazine", C. Valenzuela
Calahorro, An. Quim. 1970. 66(2), 149-56; Chem.'Abs. 73., 86772v
(1970).
(67) "Determination of Simazine, Atrazine, and Propazine in Biological
Media by Thin-Layer Chromatography", L. S. Samosvat, et al., Gig.
Sanit. 1970. 35(9), 64-6; Chem. Abs. 73, 129768t (1970).
(68) "Modified Detection.of Triazine Herbicide Residues and Their
Hydroxy Derivatives on Thin-Layer Chromatograms", S. Koudela,
J. Chromatogr. 1970. 53(3), 489-91; Chem. Abs. 74, 52318g (1971).
1971
(69) "Hygienic Characteristics of Working Conditions and the Health
Status of Workers Producing Some Triazine Herbicides", V. M.
Blagodatin, et al., Gig. Tr. Prof. Zabol. 1971. 15(1), 45-7;
Chem. Abs. 74, 79248w (1971).
(70) "Investigation of Flavones as Fluorogenic Spray Reagents for
Organic Compounds on a Cellulose Matrix. II. Detection of Pesti-
cides", V. Mallet, et al., J. Chromatogr. 1971. 56(1), 69-77;
Chem. Abs. 74, 123973e (1971).
227
-------
(71) "Thin-Layer Chromatographic Procedure for the Detection in Soils
and Waters of Herbicide Residues Commonly Used in Saskatchewan",
A. E. Smith, et al., J. Chromatogr. 1971. 57(2), 303-8; Chem.
Abs. 75, 4307b (1971).
(72) "Collaborative CIPAC Study of Titrimetric Methods for the Assay of
Methylthio- and Chlorotriazines", H. P. Bosshardt, J. Assoc. Offic.
Anal. Chem. 1971. 54(4), 749-55; Chem. Abs. 75, 47749q (1971).
(73) "2,3-Dichloro-6-amino-s-triazine,s", S. A, Agripat.Ger. Offen.
2,032,861, June 9, 1971; Chem. Abs. 75, 76850w (1971).
(74) "Infrared and Ultraviolet Spectra of Seventy-Six Pesticides",
R. C. Gore, J. Assoc. Offic. Anal. Chem. 1971. 54(5), 1040-82;
Chem. Abs. 25, 117202g (1971).
(75) "Electrolytic Conductivity Detection of Some Nitrogen-Containing
Herbicides", W. P. Cochrane, J. Chromatogr. 1971. 63(2), 364-9;
Chem. Abs. 76, 122725e (1972).
(76) "Electrochemical Purification of Waste Waters From Simazin
Manufacture", T. L. Shkorbatova, et al., Vodosnabzh., Kahaliz.,
Gidrotekh. Sooruzh. Mezhvedom. Respub. Nauch.-Tekh. Sb. 1971. No.
13, 81-9; Chem. Abs. 2Z» ^39Qz (1972).
1972
(77) "Photochemistry of Bioactive Compounds. Solution-Phase Photo-
chemistry of Symmetrical Triazines", B. E. Pape, et al., J.
Agr. Food Chem. 1972. 20(2), 316-20; Chem. Abs. 26, 112383c
(1972).
(78) "Routine Method for Identification of Pesticide Residues of
Triazine, Carbamate, Urea, and Uracil Type Compounds by Thin-
Layer Chromatography", W. Ebing, J. Chromatogr. 1972. 65(3),
533-45; Chem. Abs. 22» 1626k (1972).
(79) "Gas-Chromatographic Data of Alkylamino-s-triazines", G. Repasi,
Magy. Kern. Foly. 1972. 78(2-3), 166-8; Chem. Abs. 77, 9940d
(1972).
(80) "Differential Scanning Calorimetry as a General Method for
Determining Purity and Heat of Fusion of High-Purity Organic
Chemicals. Application to 64 Compounds", C. Plato, Anal. Chem.
1972. 44(8), 1531-4; Chem. Abs. £7, 69809c (1972).
(81) "Gas Chromatographic Determination of 2-chloro-4-«(ethylamino)-6-
(isopropylamino)-s-triazine Herbicides", M. Vajda, et al.,
Nehezvegyip, Kut. Intez. Kozlem. 1972. 4, 195-200; Chem. Abs.
27, 148327X (1972).
228
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TRIFLURALIN
1. "Determination of Trifluralin Formulations", F. J. Holzer et al., J.
Assoc. Offic. Agr. Chemists, 46(4), 659-62(1963; Chem. Abs. 59, 10703g
(1963).
1964
2. "Residue Analysis of Various Fruits and Vegetables Treated with DCPA,
Prometryn, and Triflural,in fozWeed Control", P. B. Manning et al., Proc.
Northeast Weed Control Conf. 18, 105-8(1964); Chem. Abs. 61, 15259b (1964).
3. "Residue Analysis of Alfalfa Treated with Trifluralin and DCPA for Weed
Control", T. W. Rerr et al., Proc. Northeast Weed Control Conf., 18,
313-14(1964); Chem. Abs. 61, 16698e (1964).
1965
4. "Separation of Trifluralin and Some Related Compounds by Two-Dimensional
Thin-Layer Chromatography", T. Golab, J. Chromatog. 18(2), 406-8 (1965);
Chem. Abs. 63, 7633e (1965).
1966
5. "Analysis of Several Vegetables for Residues of Trifluralin, Prometryne, or
Prometryne Plus Atrazine", T. W. Kett et al., Proc. Northeast Weed Control
Conf. 20, 106-8 (1966); Chem. Abs. 64, 18300e (1966).
6. N,N-Disubstituted 2,6-Dinitroaniline Herbicides", Eli Lilly & Co. U. S.
Patent 3,257,190, June 1966; Chem. Abs. 65, 13606e (1966).
1967
7. "Fate of Trifluralin in Soils and Plants", 6. W. Probst et al., J. Agr.
Food Chem. 15(4), 592-9 (1967); Chem. Abs. 67, 63200u (1967).
8. "Metabolism of Trifluralin- C in Carrots", T. Golab et al., J. Agr. Food
Chem. 15(4), 638-41 (1967); Chem. Abs. 67, (1967).
9. "Trifluralin" J. B. Tepe et al., Anal. Methods Pestic., Plant Growth Regul.,
Food Additives 1967, 527-35; Chem. Abs. 70, 96517p (1969).
1969
10. "Trifluralin and Related Compounds", G. W. Probst et al., Degradation
Herbic, 1969, 255-82, Edited by Kearney, P. C. et al., Marcel Dekker, Inc.
New York, N. Y.; Chem. Abs. 71, 59850w (1969).
229
-------
11. "Effect of Herbicides on Soil Microorganisms", W. W. Fletcher, Proc. Brit.
Weed Contr. Conf., 8th 1966, 3, 896-906, British Weed Contr. ..Counc., London,
England; Chem. Abs. .71, 29407q (1969).
12. "Detection of Trifluralin Vapors in Air", M. L. Ketchersid, Weed Sci. 1969,
17(4), 484-5; Chem. Abs. 72, 2431b (1970).
1970
13. "Soil Analysis of Trifluralin Methodology and Factors Affecting Quantisation",
R. M. Harrison et al., Agron. J. 1970, 52(6), 778-81; Chem. Abs. 2£t 30911t
(1971).
14. "Report on Herbicides and Plant Growth Regulators", 6. Yip, J. Ass. Offic.
Anal. Chem. 1970, 53(2), 358-60; Chem. Abs. 73, 6522a (1970).
15. "Water Monitoring System for Pesticides in North Carolina", T. J. Sheets,
et al., U. S. Clearinghouse Fed. Sci. Tech. Inform., PB Rep. 1970, No.
189291, 109 pp, avail. CFSTI from U. S. Govt. Res. Develop. Rep. 1970,
70(7), 126; Chem. Abs. 73, 54927h (1970).
16. "Persistence of the Herbicide Trifluralin in Various Types of Soils", 6.
Petrosini et al., Agrochimica 1970, 14(2-3), 123-36; Chem. Abs. 73, 24093r
(1970).
17. "Preliminary Results of Determination of Trifluralin Residues in Soil and
Their Agronomic Interpretation", P. Fusi, Notiz. Mai. Plante 1970, No.
82-83, 105-15; Chem. Abs. 74, 52366w (1971).
1971
18. "Determination of Trifluoralin in Formulations by Gas Chromatography",
L. G. Rambleton, J. Ass. Offic. Anal. Chem., 1971, 54(1), 125-7; Chem. Abs.
74, 75516J (1971).
19. "Gas Chromatographic Determination of N-butyl-N-ethyl-or,a,or-Trifluoro-2,6-
Dinitro-p-Toluene and a ,or ,or-Trifluoro-2,6-Dinitro-N,N-Dipropyl-p-Toluidine
in Formulations", M. Fuzesi, J. Ass. Offic. Anal. Chem., 1971, 54(3), 711-12;
Chem. Abs. 75, 4310x (1971).
20. "Investigation of Flavones as Fluorogenic Spray. Reagents for Organic Compounds
on a Cellulose Matrix. II. Detection of Pesticides", V. Mallet et al.,
J. Chromatogr. 1971, 56(1), 69-77; Chem. Abs. 74,123973e (1971).
21. "Thin-Layer Chromatographic Procedure for the Detection in Soils and Waters
of Herbicide Residues Commonly Used in Saskatchewan", A. E. Smith et al,
Chromatogr. 1971, 57(2), 303-8; Chem. Abs. 75, 4307b (1971).
22. "Electrolytic Conductivity Detection of Some Nitrogen-Containing Herbicides",
W. P. Cochrane et al., J. Chroma togr. 1971, 63(2), 364-9; Chem. Abs. 26,
122725e (1972).
230
-------
23. "Characteristics of the Substituted Dinitroaniline Herbicides, Treflan,
Balan, Paarlan, and El-119", D. H. Ford et al., Proc. Annu. Weed Conf.,
1971, 23, 142-50; Chem. Abs. 75, 117400v (1971).
1972
24. "Persistence of Trifluralin in Small Field Plots as Analyzed by a Rapid
Gas Chromatographic Method", A. E. Smith, J. Agr. Food Chem., 1972, 20(4),
829-31; Chem. Abs. 77. 110378b (1972).
25. "Determination of Fluorine and Bromine in Halogenated Herbicide Residues
in Soil by Spark-Source Mass Spectrometry", S. C. long et al., Anal. Chem.,
1972, 44(6), 1069-72; Chem. Abs. .77, 44150t (1972).
26. "Infrared Analysis of Pesticide Formulations", S. W. Goza, J. Ass. Off.
Anal. Chem. 1972, 55(5), 913-17; Chem. Abs. 2Z» 16089s (1972).
27. "Quantitative Analysis of Busulfan in Boil Weevils by Gas Chromatography",
Dennis R. Sukkestad, Diana L. Cardwell, J. George Pomonis, Dennis R. Nelson,
(Metab. Radiat. Res. Lab., Agric. Res. Serv., Fargo, N. Dak.), J. Econ.
Entomol., 1972, 65(2), 353-6 (Eng); Chem. Abs. 77, 15363 (1972).
231
-------
APPENDIX B
REACTIONS AND POTENTIAL IMPURITIES
-------
STEP 1
NOCL +
Nltroayl Chloride
STEP 2
MCH^CCICH - BOM j +
L —12
(013 )2e
laobutylene
HeSNa
Sodium
Methyl Msrcaptlde
-16°C
EtOH
Reflux
S hra
.CC1CH HOH
2-Chloro-2»methyl-l-nltrosopropeM dicer
yield SOX, recry'd, EtoH
(CH3)2C(SCH,J)CH-NOH •*• KaCl
2-»ethyl-2-thloB»ethyl proplonaldoxlae
yield 80%, distilled 75-81°C
to
STEP 3
(CH3)2(SCR3)CCH-«OH -f
Methyl laoeyenate
Acetone
Bu2Sn(OAc)2
Reflux, 2 hra
(CH3)2C(SCH3)CH-MO COKHCHj
2-iMthyl-2-thloaMthyl proploneldehyde
N-nethylcarbamoyloxlae
yield 85%. recry'd
FIGURE B-l. SYSTHESIS OP ALDICARB
-------
TABLE B-l. REACTIONS OCCURRING DURING ALDICARB PRODUCTION
Leaction _ , . , „ .
[Number _ Generalized Reaction _
1 R8C=CH8 + NOCl - RaCClCH8NO £ R8CC1CH=NOH £ [ Ra CC1 CH=NOH ] a
2 RaC-CH8 + NOCl -» RaC(NO)CH8Cl
3
RCH=NOH g » RCHO
5 RCHO ^ RCOOH
6 RC1 + CHgSNa - RSCH3
7 RC1 CjUg0"* ROCaHg
OH~
8 RC1 ^-^ ROH
OH~
9 RC1 + ROH *2-+ ROR
10 RCH=NOH + RC1 - RCH=NOR
11 RCH-NOH H- RC1 - RCH-NRO
12 RSCHg > RSOCHg
13 RSOCH3 IH> RSOaCH3
14 RCH-NOH + CH3NCO - RCH-NOCONHCH3
15 RCH=NOH -f CH3NCO - RCN + CH3NH8 + C0a
16 CHgNCO ^S2^. CH3NHa + C08
17 CH3NHa + CHgNCO - CH3NHCONHCH3
18 R-OH + CHaNCO - ROCONHCHg
19 RCOOH + CHgNCO - [ RCOOCONHCH3 ] - RCONHCH3 + COB
233
-------
TABLE B-l. (Continued)
Reaction
Number Generalized Reaction
20 RCH=NOCONHCHg + CHjjNCO - RCH-NOCON (CONHCH3 ) CH3
21 RNHCONHCH3 + CHgNCO -» RNHCON (CONHCH3 )CH3
22 RCHO + CH3COCH3 ^-r* RCH-CHCOCH3
23 BuBSn(C^c)a HB° » BuBSnO
234
-------
TABLE B- 2. POSSIBLE CONTAMINANTS IN ALDICARB
No.
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
"20
21
Contaminant
1
1
1
1
1
1
1
2
2
2
2
2
2
2 or St
2
2
2
2
2
2
2 or St
2
2
Likelihood of
Being Present in
Final Product
0
+
0
0
0
0
0
•H-
+
+
4
0
0
•f
0
0
0
0
0
0
0
235
-------
TABLE B-2. (Continued)
No.
22
23
24
25
26
. 27
28
29
30
31
32
33
34
35
36
37
38
•
39
Contaminant
2
2
2
2
2 or St
2
2
2
2
2
2
2
2
2
2
2
2 or St
2
2
2
2
2
2
2
2
2
2 or St
2
2
2
2
2
Likelihood of
Being Present in
Final Product
0
0
0
0
0
0
0
0
0
0
0
0
• - .
0
0
0
0
0
0
236
-------
TABLE B-2. (Continued)
Mo.
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
• 58
59
60
Contaminant
(CH3)9C[OC(CH3)8COOH)CH8NOa
(CH3)aC(NOa)CH8OCHaC(NOa)(CH3)8
(CH3)sC(NOa)CHaOC(CH3)aCHO
(CH3 )8C(N03)CH8OC(CH3 ),COOH
(CH3)8C[OC(CH3)aCHO]CHO
(CH3)aC[OC(CH3)8COOH]CHO
(CH3 ) 8C [ OC (CHa ) 8COOH ] COOH
(CH3 ) 8CC 1CH-NOC (CH3 ) 8CH-NOH
(CH3 ),CC1CH=NOCH8C(NO) (CH3 )8
(CH3)8CC1CH-NOC(CH3 )8CH8NOa
(CH3 )8CC1CH-NOCH8C(N08) (CHj )a
(CH3 )8CC1CH-NOC(CH3 )8CHO
(CH3 )8CC1CH=NOC(CH3 )8COOH
(CH3 )8C(SCH3 )CH-NOC (CU3 )8CH"NOH
(CH3 ) 8C (SCH3 )CH-NOCHaC (NO) (CH3 ) 8
(CH3)8C(SCH3)CH-NOC(CH3)8CH8NO,
(CH3)8C(SCH3)CH-NOCH8C(N08)(CH3)a
(CH3)8C(SCH3)CH-NOC(CH3)8CHO
(CH3 ) 8C (SCH3 ) CH-NOC (CH3 ) COOH
(CHa )gC(OC,H6 )CH-NOC(CI13 ),CH-NOH
(C113)8C(OCBH6)CH-NOCH9C(NO) (CH3)a
Precuraor
4 + 25
7+22
39
5+23
5+24
6+23
5+25
7+23
42
6+24
6+25
7+24
44
7+25
45
2+2
2+3
2+4
2+5
2+6
2+7
51
6 + 2
8+3
8+4
8+5
8 + 6
8 + 7
57
14+2
14+3
Reaction. .
Number Xb)
9
9
5
9
9
9
9
9
5
9
9
9
5
9
5
10
10
10
10
10
10
5
10
10
10
10
10
10
s
10
10
Step(c>
2
2
2 or St
2
2
2
2
2
2 or St
2
2
2
2 or St
2
2 or St
2
2
2
2
2
2
2 or St
2
2
2
2
2
2
2 or St
2
2
Likelihood of
Being Present In
Final Product
0
0
0
0
0
0
0
+
0
0
0
0
0
+
0
0
0
0
0
0
0
237
-------
TABLE B-2 (Continued)
No.
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
Contaminant Precursor ' ^ °b *b
CCHa )8C (OC8H6 )CH-NOC (CHa )8 CH8N08
(CH,)8C(OC8HB)CH=NOCH8C(N08)CH,)8
(CH, >8C(OC8H5 )CH=NOC(CH3 ) 8CHO
(CH, )8C(OC8Hs )CH-NOC(CH, )8COOH
(CH3 ) 8C (OH)CH=NOC (CH3 ) 8CH-NOH
(CH3 )8C(OH)CH«=NOCH8C(NO) (CH, )8
(CH3 ) 8C (OH) CH-NOC (CH3 ) 8CH8N03
(CH3)8C(OH)CH-NOCH8C(N08)(CH3)8
(CH3 ) ,C (OH)CH-NOC (CH3 )8CHO
(CH3 )8 C (OH ) -NOC (CHg ) 8COOH
(CH, )8CC1CH=N(0)C(CH3 )8CH-NOH
(CH, )8CC1CH-N(0)CH8C(NO) (CH, )8
(CH, )8CC1CH=N (0)C (CH3 )8CH8N08
(CH3 ) 8CC1CH=N (0) CH8C(N08 ) (CH, ) 8
(CH,)8CC1CH=N(0)C(CH,)8CHO
(CH3)aCClCH=N(0)C(CH3)8COOH
(CH, ) 8C (S CH3 ) CH-N (0) C (CH3 ) 8CH-NOH
(CH, )BC(SCH, )CH-N (0)CH8C(NO) (CH, )8
(CH, )8C(SCH, )CH-N(0)C(CH3 )8CH,NOa
(CH, )aC(SCH,)CH-N(0)CHaC(N08) (CH,)8
(CH, )8C(SCH, )CH«N (O)C(CH, )8CHO
(CH3)8C(SCH3)CH-N(0)C(CH3)COOH
14+4
14+5
14+6
14+7
20 + 2
20+3
20+4
20 + 5
20+6
20 + 7
69
2+2
2+3
2+4
2+5
2+6
2 + 7
75
8 + 2
8+3
8+4
8+5
8+6
8 + 7
8
10
10
10
10
10
10
10
10
10
10
5
11
11
11
11
11
11
5
11
11
11
11
11
11
5
(v Likelihood of
) Step Being Present in
Final Product
2
2
2
2
2
2
2
2
2
2
2 or St
2
2
2
2
2
2
2 or St
2
2
2
2
2
2
2 or St
0
0
0
0
0
0
0
0
0
0
+
0
0
0
0
0
+
0
0
0
0
0
83 (CHa)8C(OC8HB)CH-N(0)C(CH9)|CH«NOH 14 + 2
11
238
-------
TABLK B-2. (CnnLimutd)
No.
84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
101
102
103
104
105
106
Contaminant Precursor ^* . {b)
Number
(ClI3)aC(OC2lls)Cl]=N(0)CII8C(NO)(CH3)a
(CH3)a,C(OC2ll3)CII=N(0)C(Clla)2CII3CII3N02
(CH3)2C(OC2H5)Cll=N(0)ai2C(N02)(CH3)3
(CH3)2C(OC2IIs)Cll=N(0)C(Clla)aCIIO
(CH3)3C(OCaII,, )CII=N(0)C(CII3)2C0011
(CII3)3C(OII)CH=K(0)C(C113)2CII=N01I
(CII3)3C(011)CI1=N(0)CH2C(K'0)(CH3)2
(CH3)2C(OII)Cll=N(0)C(Cll3)2CllgCIIaCH2NOa
(CH3 ) 3C (Oil ) CII=N (0) CH2C (N02 ) (CH3 ) a
(C113)8C(OH)C1I=N(0)C(C113)2CHO
(CII3 )£C (OH) CH=N (0)C (CH3 ) 2COOH
(CH3);.C(SOCH3)CH=NOH
(CH3)2C(NO)C1I2SOCH3
(CH3)2C(SOCn3)CH3NOa
(CH3)aC(N03)CH3SOCH3
(C1I3)2C(SOCH3)CI10
(Cii3)3f;(socii3)coon
(Clla )2C(S03CI13 )CII^NOI1
(cn3)2c(NO)cii2soacn3
(CII3 )j,C(S02CH3 )CllaNOa
(CH3)aC(N03)CII2SOaCII3
(CH3)aC(SOaCll3)CHO
(CJIa)aC(S03Cll3)C0011
14 + 3
14 + 4
14+5
14+6
14+7
87
20 + 2
20+3
20+4
20+5
20+6
20+7
93
8
9
10
11
12
13
99
8
9
10
11
12
13
11
11
11
11
11
5
11
11
11 .
11
11
11
5
12
12
12
12
12
12
5
13
13
13
13
13
13
5
,» Likelihood o£
i Step Being Present in
Final Product
2
2
2
2
2
2 or St
2
2
2
2
2
2
2 or St
2 or St
2 or St
2 or St
2 or St
2 or St
2 or St
2 or St
2 or St
2 or St
2 or St
2 or St
2 or St
2 or St
0
0
0
0
0
0
0
0
0
0
0
+
0
0
0
0
0
•f
0
0
0
0
0
239
-------
TABLE B-2. (Continued)
No.
107
108
109
110
111
112
113
114
115
116
11V
118
119
120
121
122
123
124
125
126
127
Contaminant Precursor „ . tb)
Number
(C!I3 )2CC1CII --NOCONHCllg
(CI13 ) aC (SCII3 ) Cll=NOCONUCH3
(CII3 )8C(OCj.H6 )C)I-NOCONI1CI>3
(CH3)2C(OI1)CII=NOCON11C113
(CII3)2C[OC(CH3)2CH-NOII]CI1-NOCON'MCH3
(CH3 )2 C ( OC (CII3 ) aCH=NOCONHCU3 J
CH=NOCONHCn3
(CH3 ) aC [ OCH8C (NO) (CH3 ) 2 ] CH-NOCONUCH3
(CH3 ) aC [ OC (C1I3 ) 3CII 8N08 ] CH---NOCOKI1C1I3
(CI13)2C[OCH2C(N08)(CH3)2]CM=NOCONHCH3
(CH3 ) 2C [ OC (CH3 ) gCHO] CI1=NOCONHCH3
(C113 ) £c: [ OC (CH3 ) gCOOll ] Cll=NOCONl!CH3
(CI13 ) 8CC 1CH<--NOC (CH3 ) gCH-NOCONIICH3
(CII3)j.C(SCH3)Cll=NOC(CH3)8Cll^NOCONHCn3
3
3
3
3
3
3
3
3
3
3
3
St
3
3
St
St
3
3
3
3
St
St
Likelihood of
Beinj» Present in
Final Product
+
Aldicarb
•H-
0
0
+
0
0
0
0
0
0
•f
0
0
0
0
0
+
0
0
240
-------
TAIH.K 11-2. (ConUmii-cl)
No.
128
129
130
131
132
133
134
135
136
137
138
139
140
141
142
143
144
145
I4r>
147
148
Contaminant
3
3
St
St
3
3
3
2
St
St
3
3
3
3
3
3
3
3
3
3
St
3
3
LlkclihooJ ol
Doing I'rcsonl in
Final Product
0
0
•H-
•f
0
•H-
+
0
4
0
0
+
•H-
•H-
0
0
0
0
0
0
•f
149 (CJI3)aCClCON'llC!l3
19
241
-------
TABU: n-.0.. (Continued)
No.
150
151
152
153
154
155
156
157
15 C
159
160
161
162
163
164
165
166
167
Contaminant
(CH3)2C(SCIl3)CONIICil3
(CH3)2C(OC21I5)CON11C1I3
(C1I3)8C(OII)CONMICH3
(Cll3)j,C(SOOIl3 )CONIIC1I3
(CI13)aC(S02CII3)CONIlCH3
(CH3 )aC(OCOMHCH3 JCONIICIL,
(CH3)2C(SCH3)CI1=NOCON(CONHCH3)CH3
(CH3 )2C(SOCII3 )C11=NOCON (CONilCH3 )CH3
(CHa )3C (SO-iCH3 )CI1=NOCON(CONHCH3 )CH3
(CH3 )2CCLCII---CHCOCI13
(CH3)aC(SCH3)CH=CHCOCII3
(CH3 )2C(OC2H&)C11=CHCOCH3
(CH3 ^(OlOCh^CHCOCHs
(CH3 )2C(OCON11C1I3 )CH=CHCOC1I3
(CH3 )2 C (S OCH3 ) CH=CHCOCH3
(CH3 )2C(SOsCll3 )C1I=CHCOCH3
•
BuaSn(OAc)a
BiigSnO
Precursor
13
19
25
100
106
153
147
152
108
156
"157
6
12
18
2.4
146
162
160
164
Cat.
166
Reaction,.
Number* '
19
19
19
19
19
13
19
18
20
12
13
22
22
22
22
22
18
12
13
—
23
Stcp(c)
3
3
3
3
3
St
3
3
3
St
St
3
3
3
3
3
3
St
St
--
St
Likelihood of
Being Present in
Final Product
+
+
0
+
0
•f
•H-
+
0
0
0
0
0
0
0
+
+
(a) Precursor rulers to Hie contaminant numbered in this table; SM = Starting material;
Cat. = catalyst.
(b) See Table »..].
(c) The step (see Tij-urc li-1) durJitp, which the contaminant might be formed; St indicates
possible formation during s;turagc.
(d) 0 = likely present only at levels below 1 ppm
+ « likely present at levels above 1 ppm but below 100 ppm.
•H- = likely present: at levels above 100 ppm.
242
-------
Step 1 4C3H7OH+P2S5 »-2(C3H7O)2P(S)SH + H2S
O, O-di-n-propyl
phosphorodithioate
Step 2 (C3H70)2P(S)SH + C12 *• (C3H7O)2P(S)C1 + HC1
O, O-di-n-propyl
chlorophosphorothioate
Step 3 2(C3H7O)2P(S)C1 + Na2CO3 Pyriding [(C3H7O)2P(S)]2O + CO2 + 2NaCl
ASPON
FIGURE B-2. SYNTHESIS OF ASPON
243
-------
TABLE B-3. REACTIONS OCCURRING DURING PRODUCTION OF ASPON
Number ' Generalized Reaction'*'
1 4ROH + PS ^ 2(RO) P(S)SH + H S
to D M £»
2 (RY)_P(Y)SH + R'OH ^ (RY) P(Y)SR' + HO
to to to
3 (RY) P(Y)SH + R'OH ^ (RY) P(Y)OR'+ H_S
£* £* &
4 (RY) P(Y)SR+ R'OH - * (RY) P(Y)OR'-f RSH
£ «
P2S5
5 (RY) P(Y)OR * (RY) P(Y)SR
c* £»
P2S5
6 (RO)2P(Y)SH * (RO)(RS)P(Y)SH + (RS>2P(Y)SH
7 (RY),P(Y)SH + HO *~ (RY) P(Y)OH + H S
2 £• £• t*
8 (RYJPY + HO ^ (RY) P(Y)OH + RYH
3 i *•
9 (RY)2P(S)OH - * (RY)2P(0)SH
10 2(RY)2P(Y)YH — (RY)2P(Y)Y P(Y)(RY)2 + H2Y
11 2(RY), P(Y)SH t°^ • (RY) P(Y) S S P(Y)(RY)
L* & £*
12 2(RY)_P(Y)SH + Cl, (RY),P(Y)SS P(Y)(RY)_ + 2HCI
£t £• £• £•
13 (RY)2 P(S)SH ^ (RY)2PSH + S
14 (RY) PSH + R'OH ^ (RY)2POR' + H2S
15 (RY)0PSH + R'OH •• (RY)7PSR' •»• HO
2 c, c
244
-------
TABLE B-3. (Continued)
Number Generalized Reaction^3'
16 2(RY),PSH t°l • (RY)_P(S)S P(RY).
17 (RY)2P(S)OR' « *~ (RY)2 P(0)SR'
18 (RY)3PS t°l»- (RY)3PO
19 (RY),P(S)SH + Cl, ^ (RY) P(S)C1
Z (• *•
20 (RO)2P(S)C1
21 [(RO)0P(S)NC^H 1 Cl ^ RC1 + C_H_N + Polymer
255 5 5
C5H5N
22 2(RO)2 P(S)C1 + H20 N^ ^Q * [(RO)2P(S)] 2O
23 l(RO).P(S)],0 + H,0 2(RO). P(S)OH
£,£,£• tt
24 (RO) P(S)OH + HO ^ RO P(S)(OH) + ROH
£» £• £•
25 ROP(S)(OH)_ + 2H.O ^ ROH + H_PO + H S
b b $ *T £t
(a) R and R' = alkyl or substituted alkyl.
Y = oxygen or sulfur.
245
-------
TABLE B-4. POSSIBLE CONTAMINANTS IN ASPON
Number Contaminant
P,S.
2 CH CH CH2OH
i CH CHOHCH
CHjCH2OH
:, . CH CM CH CH OH
,CHiCH/:H20,2P(S(SH
7 |(C.HJi.,CHO|2PiSISH
8 iCH CH,O| PlSJSH
tn.CA0,2PtS,SH
10 |n-C3H,Ol2tn-C3H7S)PS
11 tn-C.HjDKPS
3 I 3
J2 ln-C3H..O)in-C3H7S)2 PS
13 (n-C .H_O>ln-C1H,S)P(S)SH
3 i 3 »
1-1 Step Product'*"
1
1
23-25 St
1
1
1
1 1
1 1
1 1
1 1
2 1
3 1
4 1
5 1
6 1
7 1
8 1
23 St
9 1
7 1
8+9 1
6 1
0
*
0
0
0
*
0
0
0
-
+•+
+
+
+
0
0
0
0
246
-------
TABLE B-4. (Continued)
Number Contaminant
IV (n-C H_O) P(S)S P(SI(n-C H O>2
20 (n-C3H?0)2 P(S) S S PtS)(n-C3H7O)2
2, (n-C3H70)2PSH
22 (n-C3H70,3P
23 ln-C3H7Ol2(n-C3H7S,P
24 ,n-C3H70,2P(S,SP(n.C3H70,2
2, (n-C3H70,2(n-C3H7S,PO
2o tn-C H.O) PO
27 CH CH CH SH
28 (n-C3H_S)3 PS
2" ln-C H.S) PO
30 C12
31 (n-C3H.O)2P(S)Cl
32 (CH.CH O) P(S)C1
35 | (CH ) CHO] 2 P(S)Cl
34 In-C H O) P(S)Cl
35 C5H5N
3o |(n-C-H_O).P(S) NC.H.]*cr
Precursor'"'
6
6
6
6
21
21
21
11
2+25
2+10
12+27
28
SM
6+30
8+30
7+30
9+30
Cat.
31+35
Probability of
Being Preaent
Reaction in Final
Number'b) Step Product(d>
10 1
11 1
12 2
13 1
14 1
15 1
16 1
17 1
4 1
4 1
4 1
18 1
2
19 2
19 2
19 2
19 2
3
20 3
*
++
0
0
0
0
*
0
0
0
0
0
**
0
0
0
*
4
247
-------
TABLE B-4. (Continued)
Number
Contaminant
Probability of
Being Preient
Reaction in Final
Precursor1*' Number'0' Step'cl Product'*"
36
21
3H Polymer (containing H, C, O, P and S)
36
21
44
|(n-CjH_0)2P(S)]20
31
22
ASPCN
40
39
17
3 or St 4+
-11 |in-C3H_0)tn-C3H7S)P(0)]20
40
17
3 or St
32
22
4i
) 0
33
22
-14
Il O
34
22
4- n-C H_OP(S)(OH),
14
24
St
39
23-25
St
39
23-25
St
(a) Precursor refers to the contaminant numbered in this table
SM - starting material
Cat - catalyst
Im-2 « impurity in No. 2.
(b) See Table B-3.
(c) The step (Figure B-2) during which the contaminant might be formed.
St indicates possible formation during storage.
(d) 0 - probably present only at levels below 1 ppm.
+ * probably present at levels above 1 ppm but below 100 ppm
++ - probably present at levels above 100 ppm.
248
-------
Step 1. 4 CH3OH
Step 2.
benzene
methanol phosphorus
pentasulfide
phthalic
anhydride
2(CH30)2P(S)SH + H2S
O,O -dimethyl- hydrogen
phosphorodithioate sulfide
H20
a
phthalimide
phthalamic
acid
Step 3.
COOH
:ONH2
phthalamic
acid
HOBr
,COOH
•NH:
anthranilic
acid
Step 4.
COOH
NH4OH
NH,
anthranilic
acid
COO NH
•NH
ammonium
anth rani late
CONH2
•NH,
anthranilamide
Step 5.
CONH2
anthranilamide
9
SlH
N^
ketobenz otriaz ine
Step 6.
II
N
ketobenzo
triazine
(CH30)2P(S)SH
paraform- O, O -dimethyl -
aldehyde phosphorodi-
thioate
HC1
2 t,
-CH2SP(S)(OCH3)2
Azinphosmethyl
FIGURE B-3. HAIN REACTIONS IN THE PREPARATION
OF AZINPHOSMETHYL
249
-------
TABLE B-5. REACTIONS OCCURRING DURING PRODUCTION
OF AZINPHOSMETHYL
Reaction
Number
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
•>•>
Generalized Reaction* a'
4 POM 4. 13 C i
(RY)2P(Y)SH + R'OH
(RY) P(Y)SH + R'OH
(RY)2P(Y)SR + R'OH
(RY) P(Y)OR zS 5t
(RY)2P(Y)SH + H20
(RY) P(S)OH 4 , *
(RY)2P(Y)OH + R'OH
fnv\ "Dfv^vw >
(KXJ I'l* )*11 »•
fnvi "P/YWTT *• •* >
/TJv^ 'Df^BTT fc
/ r> v \ OCU -i D'OU ^_
(K.Yj_i^orl T xv.vJrl
(RY) PSH + R'OH —
/nv^ 'P'?!? *• •* * (n
(RY)2P(Y)YH + R' Cl
(RY) P(Y) + R'Cl —
(RY)_P(Y)YH + R' N*
£ £*
£» j
£• j
/r>("«^\MU 1 TJ f~\ ^^^__
orOMM , Mfc PM1
te 7/DO\ O/Q^QW J. W Q
^ fcVr\.w^_x^\oyorl T *1— S
>- (RY)2P(Y)SR' 4- H2O
w /TJV\ TS/V^OTJ1 a T.T B
£f £
^ — ** (RY)2P(Y)OR' + RSH
-.(RY) P(Y)SR
^ (RY)2P(Y)OH + H2S
. (RY)2P(0)SH
>- (RY)_P(Y)OR' + H_0
£» £*
- (RY)_P(Y)YP(Y)(RY), + H_Y
£• c* £•
(RY).P(Y)SSP(Y)(RY),
£* £t
(RY) PSH + S
^ /OV\ "DOD1 J. U C
>• (RY) PSR1 + HO
£* &
.Y)2P(S)SP(YR)2
+• (RY)2P(Y)(YR') H- HC1
+• (RY)2(R'Y)P(Y) + RC1
fc /pr*O\ MM 4. M O
—^ \K.\*>\J) _iNri T n~\J
fc yoff\c\v
w fti\.\j\j\jf\
•» P t~T\C\l3 4. Pr'OMM
HT 4- nn
250
-------
TABLE B-5. (Continued)
Reaction
Number
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
3'4.
35.
36.
37.
Generalized Reaction^
b £•
A i-TO^ 4. A 1-TJT4 fc A T-TM-WMHA T>
& £•
2 2
A T-M® * A rN-NA T-
ArN® 2Q ArOH
^" U ^^ ^. TT^^ 1 w ^* 1 ^** TT ^N f^Tf f* |
P NW 4. C"Vf C> > P Nf"H OU
2 2
DOU 4. tir"l w^ T> /"I
jXvPi T r^^i ^ zvox
fRYl PS !• -1 fc (RYJ PO
/DV\ "DV J. U Q ' a / TT V \ 'D/V\«^tJ J. DVU
• £. • • ~* • £.
[o]
(a) R = alkyl or aryl group; Ar = aryl group; Y = oxygen or sulfur.
251
-------
TABLE B-6. POSSIBLE CONTAMINANTS IN AZINPHOSMETHYL
No, Contaminant
1 P »
1 .CH^P.SISH
! iCH^yf.HjSiPS
4 iCH^ijPI
* (CH GiiOl (!>. Hh
' i( M Giif || biHiSiSM
1 't
* K.H Gl^Pl&lOH
I '^ ' '*
10 if. ll(0i PlbiSPifcuOCH 1
II (f II Gi1Hihl!iSJ->i.SilGCH 1
,-• .M.^WM
1. .UI,G,tH
14 iCH.UyCH^PH
«'".' '!>'"> ' ' ' t'^
,-. .fM^.^ril.s.PO
|i if.M Oi PO
18 iCH GuCH hlflbifeH
" ®f>
O
(§£>'
t"
^^^ i oOH
' ' C3 COUM
-- (StfONn!
-^w, COOH
"M 1^1 CO''%M/
^XXy COOH
" _C9J XH,
" ©^
/" ^^[ V((
" ©""'
" © v
'" © ^*
Pr«curior('
SM
1
2
2
8
J
2
9
70
1
2
2
2
12
12
12
9
9
2
SM
19
IV
20
2J
20
21
2i
22
24
26
2»
21
Reaction
>) NumbarW
-
1
2
J
4
t
i
i
0
6
7
9
10
II
12
1)
14
2
J
4
-
II
IV
20
2)
21
23
22
22
2}
24
24
24
Llkt llhood of
Balnf Pratanl In
ft«p(el final Produatfd'
1 0
1 4
1 ««
1
1
1
1 «•
1 «
1 or ft «
1 4
SI
1 4
1 ««
1 '
1 0
1 4
1 4
1 0
1 f
1 •
1 0
2 o
2 o
2 4
2 4
4
2 4
4
1 4
3 o
4 ' 44
> 0
i
» 0
-------
TABLE B-6. (Continued)
Nu,
ConUmlntnl
R«*cilon
Pr«eur*of'*' Numb*r*b>
Likelihood of
Biinf Pr«f«nt In
7lMl Pf(Klutl(dl
10
COOH
24
24
COM! ,
27 « 2b
24
27 « 24
2*
[01 N
27 « 24
2»
27
2i>
N \MI(U
27 • 2t,
2u
\ •, MI< o
27 « 22
20
COOH
VMICC
27« 2)
2o
Ml ,
Nil,
NMH C)
21 « 2b
26
V'.IK.O
JO « 26
2l>
M""iTJ
27
27
21 < 27
27
)0 « 27
27
21 « 27
27
21
253
-------
TABLE B-6- (Continued)
No. Contaminant
X^v COOH
.^^. COXH,
"' ©OH
S>* OH
48 foT
l^X1" OH
X"^ COOH
" @OH
=,0 iCH.Ol
-.1 MCH.OCII ,C.l
(J
II
0
II
o
o
o
II
X^C»\CH,OH
•-,.. HOCIIjfoJ •!; "
V
fCV< »NCH,CI
-7 MUCH«2Z\.\ "
9,
"° 12-^ X NNitril^OHlCO _x*s/
-I fot CON"" ^"^
t^*- N-XXiCH^CIlCO _x*S,
"2 f^T C°NH;! CONH2
•^x^ X- \XiCH, OH iCO_X*S
03 foT C°NH2
Vix1- N NN|CH2CIICO_^IS|
Precur»or'*'
30* 27
27
26
29
30
SM
50
34
71
52
34
54
52
53
5b
55
58
57
35
oO
3b
62
Reaction
Number*0'
28
29
29
29
29
30
31
35
33
32
33
32
32
33
33
32
32
32
31
33
31
33
Likelihood at
Being Present in
Step Firul Product
5 o
5 ••
5 o
5 o
5 o
6 *,
u <
6 •>
St
Cl +*
b o
0 »
6 o
0 0
b
b o
b
b •>
b
b o
b o
b o
b o
CONf
04
2 COOH
ol
37
31
254
-------
TABLE B-6. (Continued)
Nu.
10
uo
,7
• ,r
70
71
7J
-
14
-s,
-•
78
7**
80
Contaminant
^~^ CONH2 COOH
NH
124- N - NN(CH2OH ICO _X*«s
*Q* N-NNlCH2CllCO_X^S
<***t COOH
'^x'* N NNiClljOHiCO — ^S"
®c:oon
\ \\.rn ( nco-^s
' - ~foj
o
II
^ — yt-vN-CN^S PiSliOCII SI2
loi ^
y*
X^^-CH2OP,SI.OCH3.2
SXX^N*'
0
jgj- --N-C:H2SP.OMOCH3I2
'sx'V •
8
rQT'^N-CH,SPlSliOCHi)lSCHJl
XX^\»-
L.
^r ^N-CH,OPlOliOCHjl2
*' o
l»
X^Y CONH ,
^sX*1 N NNlCH^SPlSMOClljljICO fol2
kx*- N NN|CH2SPiSliOCHJi2lCO-rQ*j
rCv CONHz COOH
>2*^ v Mvlr-u D nr-u ICO -t^^i
Z i'2 -Jg|
'sx*' N .NNlCH2SPtShOCH3l2lCO Yol
Precursor'*'
64
38
,b
J"
t>8
52 •> 2
5) + 2
52 + 8
52-2
72
52+9
53-9
70
52+6
53 + b
52+7
52+9
54+2
55+2
56+2
57+2
58+2
59+2
60 + 2
bl + 2
62+2
03+2
64
65
66
07
Reaction
Number*0'
33
31
33
31
33
2
IS
8
3
36
2
15
34
2
15
8
3
2
15
2
2 + 15
2 + 15
15
2
15
2
15
2
IS
2
15
Likelihood of
Being Precant ii
Step'el Final Product'0"
6 o
6 o
6 o
6 o
o o
b Azinphot-
b methyl
6 ++
6
St
6 ++
6
St
6 ++
6
6 +
6
6 +
b
b +
6
6
6
b o
6
6 o
6
6 o
6
b o
6
255
-------
TABLE B-6. (Continued)
Likelihood of
Nu. Contaminant
XX, COOH NH,
c i foT j^ z
^* \ XN|CH2SPlSHOCHJl2) col"o]
Precursor'*'
68
b9
Reaction
Number"1'
2
15
Step
b
b
Being
Final
Precent in
Product<<»
o
P'SliOCHji,
34 i Z
17
C.OOII
Ml P'Si'UCH I,
24 - 2
17
CONHj
NH PoiiOCHjl,
2t> •» 2
17
,
\\IHiSliOCHji, I
31 + 2
IT
NH,
35-2
17
17
CUMI,
.,
J _
iCH Ol,PiSlSC»!,OCH CI
ICH ,Oi ,
4o - 2
SI i 2
51 + 2
IS
IS
70
35
St
02
C:H?SI;
91
746
35
37
St
St
St
(•) Precursor refers to the contaminant numbered in this table. SM -
(b) See Table B-5.
(c) The step (Figure B-3) during which the contaminant might be formed
St indicates possible formulation during storage *
(d) 0 - likely present only at levels below 1 ppm
+ - likely present at levels above 1 ppm but below 100"ppm
•H- - likely present at levels above 100 ppm.
256
-------
Step 1. CH2=CCH2C=O + CH3NH2 M .j» CH3COCH2CONHCH3
l-o-l e yarmne
Ketene Dimer N-Methylacetoacetamide
Step 2. CH3COCH2CONHCH3 + SC^C^ —»-CH3COCHClCONHCH3 + SO2 + HC1
Sulfuryl 2-Chloro-N-Methylacetacetamide
Chloride
Step 3. PC13 + CH3OH —»• (CH3O)3P
Trimethyl Phosphite
Step 4. CH3COCHC1CONHCH3 + (CH3O)3P —»-(CH3O)2P(O)CH(CH3)=CHCONHCH3 + CH3C1
AZODRIN
FIGURE B-4. SYNTHESIS OF AZODRIN
257
-------
TABLE -B-7. REACTIONS OCCURRING DURING PRODUCTION
AND STORAGE OF AZODRIN
Reaction
Number Generalized Reaction
1. CH2=CCH2C=O + RNH2 —•> CH3COCH2CONHR
I—o-l
2. CH2=CCH2C=O + H2O —*• CH3COCH2COOH
I—0-1
3. CH3COCH2COOH —» CH3COCH3 + CO2
4. RCH2COR' + SO2C12 —» RCHC1COR1 + SO2 + HC1
5. RCHC1COR + SO2C12 —•• RCCi2COR' + SO2 + HCl^
6. ROH + PC13 —*- ROPC12 + HCi
7. ROPC12 + ROH —»• (RO)2PCl + HCI
8. (RO)2PC1 + ROH —^ (RO)3P + HCI
9. (RO)3P + HCI —» (RO)2POH + RC1
10. (RO)2POH + HCI —•• ROP(OH)2 + RC1
[O]
11. (RO)3P —»• (RO)3PO
12. (RO)3P + R'CH2COCHC1R' —* (RO)2P(O)OC(R'CH2)=CHR' + RC1
13. (RO)3PO -I- H20 —^ (RO)2P(O)OH + ROH
14. (RO)2P(O)OH + H20 —•> ROP(O)(OH)2 + ROH
A
15. (RO)2P(0)OC(R'CH2)=CHR" —* (RO)2P(O)QH + [R'CH=C=CHR"]X
16. RCONHR1 + H2O —^ RCOOH + R'NH2
17. (RO)3PO + R'NH2 —^ (RO)2P(C)NHR' + ROH
258
-------
TABLE B-8. POSSIBLE CONTAMINANTS IN AZODRIN
Number
Contaminant
Likelihood of
Being Present
Reaction in Final
Precursor**' Number*5' Step*c> Product**"
1 CH, = CCH,CO
2
SM
10
C1CH2COCHCICONHCH3
SM
CM COCH CONHCH
1+2
CM COCH2COOH
CH COCH3
CH COCHCICONHCH
CM COCCI CONHCH
CICH2COCH2CONHCH3
SM
12
11
SM
14
CH^OH
SM
(CH OIPCI
lit 14
lCHJ0)2PCl
14415
17
14+16
18
17
19 CH OP(OH)
18
*
10
259
-------
TABLE B-8. (Continued)
Number
Contaminant
•Likelihood of
Being Present
Reaction in Final
Precursor'*' Number'0' Step'c) Product'*1'
20
Pi OH)
19
10
CH Cl
17+7
12
(CH^OI^PO
17
11
3 or St
iCHjOl,P(0)OC(CH3)--CHCONHCH3
17+7
12
Azodrin
21
iCH3O(2PtOlOC(CH3l =
17+8
12
ICHJ0)2P(0»OCICH2CONHCH3)=CH2
17+9
12
(CH O),PlO)OC(CH ClhCHCONHCH
17+10
12
17+11
12
2ti (CHJO)JP(O)OC(CH2Cl)=CH2
17+ 1Z
12
(CH O)2PiO|OH
23
13
4 or St
++
JO
CH OPiOMOH)
29
13
4 or St
++
51
1 CM,-C-CONHCH |
23
15
4 or St
++
32
ICH O)2PlO)OCtCH )=CHCOOH
23
16
4 or St
33
(CH O)2P|O)NHCH3
23+2
17
4 or St
(CHJOHCHjNH)PiO)OC(CH3l--CHCONHCH3
23+2
17
4 or St
(a) Precursor refers to the contaminant numbered in this table
SM - starting material.
(b) See Table B-7.
(c) The step (Figure B-4) during which the contaminant might be formed.
St indicates possible formation during storage.
(d) 0 - likely to be present below 1 ppm.
+ » likely to be present above 1 ppm but below 100 ppm.
++ • likely to be present at levels above 100 ppm.
260
-------
H
Step 1. CH3CH200 -I-
OT
methyl ethyl urea
ketone
Ni cat.
CH3CH2CH(CH3)NHCONH2
N-sec-butylurea
0
II
C
Step 2. CH3CH2CH(CH3)NHCONH2 + CH^OCHgCOOC^ - *• CH3CH2CH(CH3>N CH + C H OH + H 0
°-\ /"CH3
N
H
N-sec-butylurea ethyl acetoacetate 3-sec-butyl-6-methyluracll ethanol
10
a*
Step 3. CH3CH2CH(CH3)N
0-C
N
H
0
II
C
CH3CH2CH(CH3>N/ CBr
0-C
' N
H
HBr
3-sec-butyl-6-methyluracll bromine
5-bromo-3-sec-butyl- hydrogen bromide
6-methyluracil
(Bromacil)
FIGURE B-5. SYNTHESIS OF BROMACIL
-------
TABLE B-9. REACTIONS OCCURRING DURING PRODUCTION OF BROMACIL
Reaction
Number Generalized Reaction
1 RR'CO + R"NHCONH0 + H_ XTfc RR ' CHNHCONHR" + H.O
i / Nn_ t.
2 RR'CO + H N1 V RR'CHOH
3 RR'CO H- R"NH2 + H2 N1 RR'CHNHR" +
A RNHCONHR' + CH.COCH^OOR" » RNHCONR'C(CH3)
5 RNHCONR'CCCHJ-CHCOOR" >- HN CH + R"OH
0«C CCH3
N
R
6 CH3COCH2COOR + H20 >• CHgCOCHg + C02 + ROH
7 RH + Br2 —>- RBr + HBr
8 RBr -I- R'NH2 fc-RNHR1 + HBr
9 RCOOR1 + R"NH2 »-RCONHR" + R'OH
10 RBr + H20 >• ROH + HBr
262
-------
TABLE B-10. POSSIBLE CONTAMINANTS IN BROMACIL
Number Contaminant Precursor
1 NH CONH, SM
2 2
2 CH3CH2COCH3 SM
3 NH3 cat.
4 CH3CH2CH(CH3)NHCOHH2 1+2
5 Cn«fcwli«t«H \l»n A / HntwWcH*H vtn^ / Un #.(*!* <* * T •(
A f*H f*H f*H f /*!$ \ftH 9
i f*u /*u /™u fftt \ uu i A i
* / Wn««OClMwu\ wliM/ Alfln it * 3
8 CH3CH2CH(CH3)NHCH(CH3)CH2CH3 2+7
9 CH3COCH2COOC2H5 SM
10 CH3CH2CH(CH3)NHCONHC(CH3)— CHCOOC2H5 4+9
0
II
c
/ \
Uf*U fU r*U ffU \ M f*H 1 f\
wn.LrCi- wn vun. /w vn AU
32 3 | ||
% o*r CCH
u tx «, 3
N
H
12 CH3COCH3 9
13 C2H5OH 10
14 Br0 SM
Likelihood of
Reaction. , . Being Present in
Number Step Final Product W)
— 1 +
— 1 0
— 1 0
11 ++
11 ++
21 0
31 0
31 0
w»w 9 ^
4 2 ' +
52 ++
62 0
52 0
— 3 0
0
II
15 CH3CH2CH(CH3)N CBr
1 , >3
N
H
11 + 14
Bromacil
16
HBr
11 + 14
17
0
II
/XCH
J I II
0-C CCH2Br
N
H
11 + 14
263
-------
TABLE B-10. (Continued)
Nv*ib«r Contcmlnim
0
n
11 OljCll^lKCH^N ttf
"" v /CV"
N
II
1 (i M.NCOMHC « M . ) — UK.OiK, .11 „
C
20 m MI
1 II
0»C tCII ,
N
M
n
M
/'\
J\ UK I Hi
1 II
"•r(") Nun»b«i
-------
TABLE B-10. (Continued)
Likelihood of
Rom Ion Baina *roooni i
Numbor Contaminant •reeuraorU) Niasborib) itop(e) final
„
;a
29
30
A '
CMjCHjClKCIIjJN Clf
> S^/ wl»m«Wm*
H
CH jCOCH | CM ( CH ,) CH jCII , ) COOC^H j
CHjCOCH^CONHCiaCHjJCHjCHj
CH.COCHCONHCH(CH.)CH.CH.
!• + 7
2S 4 7
9 4 7
29 4 14
1
8
9
7
3
3
2
3
4
0
0
0
If
CH]COCH[Clt(CM))CH2CH))CONHCH(CH])CH2eH) JO * 7
1
32 CHjCH3CH(CHj)M CBr II 10
. .
H
H
(a) Procurior rofor* to tha contaminant numbered in thta tabla, IM • atartlng
matorlalt cat, • catalyat.
(b) laa Tablo B*9.
(c) Tho Htap (Figuro B-3) during whioh tha contaminant Bight bo foraod,
(d) 0 • likoly to bo proaont at lavala balow 1 ppm
-------
Step 1 CKa-CHCH-CKa +
CH-C-
butadiene
maleic anhydride
A -tetrahydrophthalic
anhydride
Step 2
u
if>S*
20°-220 c
\X^ u ammonia
^
-tetrahydrophthalic
anhydride
VI—Til
A -tetrahydrophthalimide
Step 3 2CS + 5C1
2CC13SC1
sulfur monochloride
carbon chlorine trichloromethane-
disulfide sulfenyl chloride
Step 4
.J
CC13SC1
3
A-tetrahydrophthalindde
trichloromethane-
8ulfcnyl chlorldc
ft ^T C
N-S-CC1
CAPTAN
FIGURE B-6. MAIN REACTIONS IN THE PREPARATION OF CAPTAN
266
-------
TABLE B-ll. REACTIONS OCCURRING DURING PRODUCTION OF CAPTAN
Reaction
Number Generalized Reaction8
CHj-CH-CH-CH- + RCH-CHR1
-
- o:
2 (RCO)20 + NH3 * RCONH2 + RCOOH
3 (RCO)20 + H£0 » 2 RCOOH
4 (RCO)2NH + NH3 » 2
5 RCOOH + NH3 -^-» RCONH2
6 2CS2 + 3C12 -=*-» 2CSC12 + S2C12
7 CSC12 + C12 » CClgSCl
8 CSC12 + 3C12 + 2H20 » CC13S02C1 + 4HC1
9 2SnCln + 2H00 > 3S + 4HC1 + S0n
10 4CC13SC1 *£-> S2C12 + 2CC14
11 2CC13SC1 + C12
12 CC1.SC1 + HjO » CC1.SOH + HC1
13 CC1,SOH + H.O > CO, + S + 3HC1
J £• £*
14 3CC13SOH > CC13SSCC13
15 CC13SOH
16 CClgSCl + (RCO)2NH ^^^ (RCO)2NSCC13
17 CC13S02C1 + (RCO)2NH ^^ (RCO>2NS02CC13
18 CClgSCl + RCH-CHR » R(CC13S)CHCHC1R
19 RCH-CHR + CC13S02C1 > RCHC1CHRCC13 + SOj
20 CSC12 + (RCO)2NH * (RCO)2NCSN(COR>2
21 (RCO)2NSCC13 -I- HjO » (RCO)2NH -I- CC^SOH
22 (RCO)2NSCC13
23 (RCO)2»H + S2C12 » (RCO)2NSSN(COR)2
24
-------
TABLE B-12. POSSIBLE CONTAMINANTS IN CAFTAN
No . Contaminant
1. CH2="CHCH=CH2
0
M
CH— C^
2. II >
CH — C
6
0
..^-^
3. : 1 ,0
^ "I
4 . HOOCCH-CHCOOH
, '^--COOH
5- 1 :
1 ^COOH
. '\-COOH
6. M ]
'< - kCONH2
9
•v -~c^
'• ij^
s^^CONR2
8. : | :
^ "CONH2
9 . HOOCCH-CHCONH2
Pre-a
cursor
SM
SM
1+2
2
3
1+4
3
5
6
22
7
6
2
4
Reactipn
Number
1
3
3
1
2
5
2
21
4
5
2
5
Likelihood of Bei«»
Present in final
Step Product
1 0
1 0
1 +
1 0
1 +
1
2 +
2
2 ++
At
2 +
2
2 0
2
268
-------
TABLE B-12. (Continued)
No.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
Contaminant
0
H
CH — Cx
|i NH
CH -C"
0
H2NOCCH-CHCONH2
CS2
csci2
s2ci2
CC1.SC1
s
eci,
cci3sscci3
cci3so2ci
CC13SOH
CC13S02H
Pre- Reaction
cursor Number
9
"
SM
12
is
13
14
20
H
»
12
15
22
20
2
i
4
5
—
6
6
10
7
9
13
10
11
10
14
8
12
21
15
14
Likelihood of Being
Present in final
Step Product
2 0
2 0
2
3 0
3 0
3 0
3
3 +
3 -H-
4 or St
3 0
3
3 +
4 or St
3 0
4 0
4 or St
4 or St +
4 or St
22.
NSCCl
0
7+15
16
CAPTAN
CH -
23. ||
CH -
NSCC1
10+15
16
269
-------
TABLE B-12. (Continued)
No . Contaminant
9
/•'\-^c
u J-^r^ 2 3
x/ 6'
0
CH — C ^
25. || NS02CC13
0
0
-.ci.cs, X-fc1^
26. f NH
ML J -C "
^" a
0
n r^ ~"\ — . C ^
ViX-VsO ^N —•' X
27 3 NSCC1,
ci J--c^ 3
6
^1 ^C ' %'^_ f*f\f*£Q
dX— UD _^ x^ v>ui/n
9fi I
e* cil JCOOH
Cl.CS x " 'X, COOH
29. 3 ; I
Cl L J CONR.
^ ^s' 2
^1 f*C ^^^^**- ^rtKTW
LJ._Lb .^ \^uiNri2
Pre- Reaction
fi. u C
cursor Number Step
7+19 17 4
22 22 4 or st
10+19 17 4
23 22 4 or st
7+15 18 4
22+15 18 4
26+15 16 4
5+15 18 4
6+15 18 4
Likelihood of Being
Present in |inal
Product
0
0
*
0
0
30.
CONR^
8+15 18 4
270
-------
TABLE B-12. (Continued)
Pre-a
No . Contaminant cursor
0
^-^^ ii
v> X A v O s^ ^^1 "^ ^^
3 I NSO CC1. 24+15
31 • ciL^"-0 26+19
p
Cl CS C — C^
32. 3 1 NH 10+15
cic-c'
0
0
n re r J*1
UJ.,^3 U L.^ 7T4.1 «»
33 ' clc_ xNSCC13 32+15
p
ape p p<
«t,& t — Cx 2S+1S
34. J | NSO CC1 ;£"
Cl C - C ' * J JZ+iy
0
35. HOOC CH(SCC13)CHC1COOH 4+15
36. HOOC CH(SCC1 )CHC1CONH2 9+15
37. H2NOCCH(SCC13)CHC1COHH2 11+15
C1C "\ C
38. 3 f 1 ^NH 7+19
o
o
39 °l3C f^^T XTJqrM 22+19
NSCC13
ni L 1 -^ r ' J Jo+lD
Reaction
Number
18
17
18
18
16
18
17
18
18
18
19
19
16
Stepc
4
4
4
4
4
4
4
4
4
4
4
4
4
Likelihood of Being
Present in linal
Product
0
0
0
0
0
0
0
0
0
271
-------
TABLE B-12. (Continued)
No.
40.
41.
42.
43.
44.
45.
s>
fi
-v
CH
Jl
CH
CH
II
CH
/'
1
CH
II
CP
CH
ll
CH
~x.
^
0
ii
— C
— C
6
0
— C
6
***" -..
i
0
ii
__ P
-(?
0
0
- C
Likelihood of Being
Pre- Reaction ^ Present in final
Contaminant cursor* Number Step0 ' Productr
0 0
%CSN^ |j 7+13 20 4 +
^A ^E'^
9
^ JC, —CH
NCSN || 10+13 20 4 0
' VC - CH
6
0
"NCSN' ' j! 7+10+13 20 4 o
vc- 'j
6 ^
P P
>TSSflT r Ij 7+14 23 4 +
6 o
9
^ C — CH
NSSN" || 10+14 23 4 0
xc -ck
6
0
^ C , " •>,
^NSSl;^ |J 7+10+14 23 4 0
272
-------
TABLE B-12. (Continued)
No.
46
47
Contaminant Precursor3
HOOCCOOH 2
(Impurity)
fpjvS, 2
L/~^ -^c; (Impurity)
0
48 HOOCCONH2 46
49
0
c
[OjT /H 47
0
50 HOOCCONHC1 48
51 HOOCCH - CHCONHC1 9
52
C^l /
J J '
s
54
0
CH C.
II >C1 10
CH .
0
X*\ P
^^•^^
X^x'^c
0
Likelihood of Being
Reaction Present in
Numberb Step c Final Productd
1 0
•
1 +
52 +
22 +
25 4 +
25 4 +
24 4 +
24 4 +
24 4 +
a. Precursor refers to the contaminant numbered in this table. SM ** starting material
b. See Table B-il.
c. The step (Figure B-6) during which the contaminant might be formed. St indicates
possible formation during storage.
d. 0 - likely present only at levels below 1 ppm.
+ = likely present at levels above 1 ppm but below 100 ppm.
++ « likely present at levels above 100 ppm
273
-------
Step I
+2HCI
N
pyridine chlorine
N
2, 6-dichloropyridine hydrogen chloride
Step '2
2, 6-dichloropyridine
H20
sodium t- butyl
hydroxide alcohol
Cl
6-chloro-2-
pyridinol
+ NaCl
sodium
chloride
Step 3
6-chloro-2-pyridinol chlorine
Cl
3, 5, 6-trichloro
2-pyridinol
+2HCI
hydrogen
chloride
Step 4
4CHOH
ethanol
P_S
phosphorus
pentosulfide
2(C,H_O),P(S) SH
£36
O,O-diethyl phos-
phorodithioate
H,S
2
hydrogen
sulfide
Step 5
(C2H50)2PS(SH)
Cl
HCl
O, O-diethyl phos- chlorine
phorodithioate
(C2H50)2P(S) Cl
O, O-diethyl chloro-
phosphorothioate
(C2H50)2 P(S)
N Cl
3, 5, 6-trichloro
2-pyridinol
O,O-diethyl chloro
phosphorothioate
Cl
Na2CO3
N
O, O-diethylO-(3, 5, 6-tricHloro
2-pyridinyl) phosphorothioate
(Dursban)
DMF
hydrogen
chloride
FIGURE B-7. SYNTHESIS OF CHLORPYRIFOS
274
-------
Step A 1
©
N
4CI,
Cl
4HCI
Cl
pyridine chlorine
2, 3, 5, 6-tetrachloro-
pyridine
hydrogen
chloride
Step A2
Cl
Cl N Cl
NaOH
HO N Cl
NaCl
2, 3, 5, 6-tetrachloro
pyridine
sodium
hydroxide
3, 5, 6-trichloro
2-pyridinol
sodium
chloride
FIGURE B-8. ALTERNATE SYNTHESIS OF 3,5,6-TRICHLORO-2-PYRIDINOL
275
-------
TABLE B-13. REACTIONS OCCURRING DURING PRODUCTION OF CHLORPYRIFOS
Reaction ':Ij,
Momber G«Mr»lU«d Reaction!
l. 4 ftfiCi
M
to 5)
2 JH->T~W'« 4 Neon ^ JLVJ-^x * N.CI
HO
(s»0 to 4}
t 2CL —*- ^fOTT * 2HCl
^
6
7
•
*
10
a
12
13
14
IS
16
17
1«
»Y)2P(Y»H 4 R'OH
(RY}2P(Y)SH 4 R'OH
(RY)2P(Y|SR 4 R'OH
(RY)2P(Y)OR - . P8^
(RY)2P(Y)SH 4 H20-
(RY)2P(S)OH ^K(RY)
2«RY),POR.S=-rtRY
|RYI2P(S^H ^(RY»2
(RY)2PSH 4 R'OH -t
(RY)2PSH 4 R'OH -4
i(RY)2P(S)SH 4 CI2-
-^(RY)2!*(Y)SR« 4 H20
— *-(RY>2P2P(Y)ORI 4 RSH
i*. (RY)2P(Y)SR
-«-(RY)2P
-------
TABLE B-13. (Continued)
Reaction
Number Generalised Reaction^*'
20 (C2H.O)2P(S)CL * HQN * ,2
(x • 1 to 4)
21 (C2H.O)2P(S)0' >l "Py (C2«50)2P(S)OH * C-H5OP(S)(OH)2
(x » 1 to 4)
2Z (C2H50)2P(SK)^ T) * wi ., (C2H$0)2P(0)0
(x • 1 to 4)
24 HO
(•) R and R* = eth/1 or •ubstituted pyridyl group
Y • oxygen or aulfur.
277
-------
TABLE B-14. POSSIBLE CONTAMINANTS IN CHLORPYRIFOS
Number
1
2
3
4
5
6
7
a
9
10
u
12
13
14
15
16
17
18
19
Contaminant
C5H5N
C12
2-Cl CeH N
2,«>-Cl2C5H3.N
2.3,6-CI3C,.H2N
2,4,6-Cl3C5H2N
2.3,4,6-Cl4 CjHN
2,3,5, o-C!4 CjHN
C15C.N
NaOH
2-OH-o-Cl C.H N
2-OH-C HN
2-OH-3, 0-C12 CjHjN
2-OH-s, 6-ci2 C.HZN
2-OH-4,6-Cl2 C^N
2-OH-3.4.6-C1 CjHN
2-OH-4, i, t>-Cl3 C.HN
2-OH-3,5.o-ClJ C^HN
2-OH-3.4, 5, o-Cl C.N
Precuraor'al
SM
SM
1+2
1+2 -
1+2
1+2
1+2
1+2
1+2
SM
4+10
3+10
5+10
5+10
6+10
7+10
7+10
2+11
35
9+10
Ukellhood of
Reaction Betaf Preaent In
Numberfbl Step(cl Final ProductW)
-
-
1
1
1
1
1
1
1
-
2
2
2
2
2
2
2
3
2
21
I
\
1
1
1
1
1
1
1 or Al
1
2
2
2
2
2
2
2
2
3
A2
St
2
e
o
o
o
o
o
o
*
o
0
0
o
o
o
o
0
o
"
o
20
Cl N
Cl
18+10
A2
CZH.OH
P,S.
21
22
24
25
20
-------
TABLE B-14. (Continued)
Number Contaminant'*)
Mi^ U rtl DfCkCCDtfCIf f\f* U 1
I w_n_ V|. ^|9|99rl9 /I WVrf _ **ml»
30 tCjH O) T Cl
Cl
.Cl
ci
(C2H50)2P(S>0 N Cl
C'xX"'O'
(C2HsO)(C2H5S)P(0)0'xSl-^<
(C2H50>2PIO)S N <
cl
HCON(CH3»2
Cl _ Cl
-ol"
C2H5OP(S)(OH>2
2, 5-(OH)2-3,6-Cl2C5HN
2, 3, 5, 6-(OH)4 C5HN
,O
18+34
14+34
13+34
16+34
17+34
19+34
35
Solv
35
35
18
18
47
20
20
20
20
20
20
14
l4
22
21
23
23
6 orSt
6 or St
6
St
St
St
St
St
Chlorpjrrifoc
(a) Precursor refers to the contaminant numbered in this table. SN • starting
•aterial. Solv * solvent.
(b) See Table B-13.
(c) The etep (Figures B-7 and B-8) du. ing shlch the contaminant .might be formed.
St indicates possible formation during storage.
(d) o - likely to be present at levels below 1 ppm
+ - likely to be present at levels above 1 ppn but below 100 ppm
++ « likely to be present at levels above 100 ppm.
279
-------
Step 1.
CH2-CCH2C-0
+ CH3OH
CH3COCH2COOCH3
Ketene Dimer
Methanol
Methyl Acetoacetate
Step 2.
[0]
Ethyl Benzene
OCH,
CHOHCH,
[H]
t
a-Methylbenzyl Alcohol
Step 3. CH3COCH2COOCH3
CH3COCH2COOCHCH3
a-Methylbenzyl Acetoacetate
Step 4. CH COCH2COOCHCH3 +
Sulfuryl
Chloride
CH3COCHC1COOCHCH3
HC1
a-Methylbenzyl 2-Chloroaceteacetate
Step 5. PC1
CH.OH
Phosphorus
Trichloride
Methanol
Trimethyl Phosphite
Step 6. CH3COCHC1COOCHCH3 -H
(CH30) 2P(0)OC(CH3)-CHI
Ciodrin
CH
FIGURE B-9. SYNTHESIS OF CIODRIN
280
-------
TABLE B-15. REACTIONS OCCURRING DURING PRODUCTION AND STORAGE OF CIODRIN
Reaction
Number
Generalized Reaction
1.
CH«-CCH«C-0 +
-.
2.
CH2-CCH
H,
.^<_
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
CH3COCH2COOH
CH2CH3
>_VVl_ V
-------
TABLE B-15. (Continued)
Reaction
Number
Generalized Reaction
16.
17.
18.
19.
20.
(RO)3P
(RO)3P + R'CH^OCHCIR1
(RO)3PO + H,
(RO)2P(0)OH
(RO) 2P (0) OC (R1 CHJ -CHR"
(RO)3PO
(RO)2P(0)OC)R'CH2)-CHRI + RC1
-»- (RO)2P(0)OH + ROH
ROP(0)(OH)2 + ROH
(RO)2P(0)OH + [R'CH-C-CaiR"]
282
-------
TABLE B-16. POSSIBLE CONTAMINANTS IN CIODRIN
M
00
No.
1
2
3
4
5
6
7
8
9
10
11
Contaminant
CH -CCHjCO
CH3OH
CH-COCH-COOCH.,
CH.COCH.COOH
3 2
CH.COCH.
3 3
@CH2CH3
/Rs
^^yCHOHCHg
@COCH3
CH,COCH9COOCHCH.
,^^^^.
(Q)
SO.Cl,
2 2
CH0COCHC1COOCHCH_
J ^x'x. •*
Precursor
SM
SM
1 + 2
1
4
9
SM
6
8
9
26
6
3 + 7
SM
9
Reaction
Numberb
-
-
1
2
3
7 + 3
-
4
6
7
7
5
8
_
9
Likelihood of Being
Present in .
Stepc Final Product
1
1
1
1
1
4
2
2
2
4
St
2
3
4
4
0
0
0
0
0
0
0
++
+*
0
++
12 CH3COCC12COOCHCH3
11
10
4
-------
TABLE B-16. (Continued)
M
00
No.
13
r,
14
15
16
17
18
19
20
21
22
23
24
25
26
Confam-lna.nt-
G1CR2GOCH2COOGHCH
(Q)
C1CH2COGHC1 COOCHCH-
CH3COCH2C1
C1CH2COCH2C1
PCI,
(CH30)PC12
(CH30)2PC1
(CH30)3P
(CH30)2P(0)H
CH3OP(OH)2
P(OH)3
CH3ci
(CH30)3PO
(CH.O) ,P(0)OC(CH,)CHCOOCHCH,
Precursor*
9
11
5
13
31
15
SM
2 + 17
18 + 2
19 + 2
20
21
22
20 + 11
20
20 + 11
Reaction
Nunberb
9
9
9
7
18
9
-
11
12
13
14
15
15
17
16
17
Likelihood of Being
Present in .
Step0 Final Product
4
4
4
6
St
4
5
5
5
5
5
5
5
6
5
6
+
0
+
0
0
0
0
+
+
+
0
0
+
Ciodrin
-------
TABLE B-16. (Continued)
K>
00
No.
27
28
29
30
31
32
33
34
35
Contaminant
(CH_0) 2P (0) OC (CH) -CC1COOCHCH
(CH 0) 2P(0)OC(GH2COOCHCH3)-CH2
(CR30) 2P (0) OC (CH2C1) -CHCOOCHCH3
(Q)
(CH30) 2P(0)OC(CH3)-CH2
(CH30) 2P(0) OC(CH2C1)-CH2
(CH30)2P(0)OH
CH3OP(0)(OH)2
[C^-OCOOCHCH^
(CH30) 2P(0)QC(CH3)-CHCOOH
Precursor*
20 -»- 12
20 4- 13
20 4 14
20 4- 15
20 + 16
26
32
26
26
Likelihood of Being
Reaction Present in .
Numberb Stepc Final Product
17 6 4
17 6 4
17 6 0
17 6 4-
17 6 0
18 8t 44-
18 St 44
20 6 4 St 44
7 6 4- 8t 44-
Precursor refers to the contaminant numbered In tM« t-nhio. SM . BfB«.«.4«» ..«...4.t
See Table B-15.
C The step (Figure B-9) durinn which the contaminant mi*ht be formed. St indicates possible formation
during storage.
0 - likely present only at levels below 1 ppm.
+ * likely present at levels above 1 ppm but below 100 ppm.
•H* likely present at levels above 100 ppm.
-------
Step 1. 4 C2H5OH + P2S5 — * 2(C2H5O)2P(S)SH + H2S
O, O-diethyl phosphoro-
dithioate
Step 2. 2 (C2H50)2P(S)SH + 3C12 — •> 2(C2H5O)2P(S)Cl + S2C12 + 2HC1
O, O-diethyl
chlorophosphorothioate
Step 3. C2H5SH + CH2CH2 C2H5SCH2CH2OH
O
ethyl ethylene 2 - (ethy Ithio ) ethanol
mercaptan oxide
Step 3 A. (Alternate)
HSCH2CH2OH + C2H5C1 + NaOH— »C2H5SCH2CH2OH
2-hydroxyethyl ethyichioride 2-(ethylthio)ethanol
mercaptan
Step 4. (C2H5O)2P(S)C1 + C2H5SCH2CH2OH —»,
(C2H5O)2P(S)OCH2CH2SC2H5
(C2H50)2P(0)SCH2CH2SC2H5
DEMETON
(mixture of above isomers)
FIGURE B-10. SYNTHESIS OF DEMETON
286
-------
TABLE B-17. REACTIONS OCCURRING DURING PRODUCTION OF DEMETON
Number Generalized Reaction^*)
1 4C2H5OH + P2S5 —•• 2(C2H5O)2P(S)SH + H2S
2 (RY)2P(Y)SH + R'OH —»• (RY)2P(Y)SR' + H2O
3 (RY)2P(Y)SH + R'OH —»• (RY)2P(Y)OR' + H2S
4 (RY)2P(Y)SR + R'OH —•• (RY)2P(Y)OR' + RSH
5 (RY)2P(Y)SH + H20 —+> (RY)2P(Y)OH + H2S
6 (RY)2P(S)OH "^ (RY)2P(O)SH
7 2(RY)2P(Y)YH —» (RY)2P(Y)YP(Y)(YR)2 + H2Y
[O]
8 2(RY)2P(Y)SH-1-*. (RY)2P(Y)SSP(Y)(YR)2
9 2(RY)2P(Y)SH + C12 —•• (RY)2P(Y)SSP(Y)(YR)2 + 2HC1
10 (RY)2P(S)OR' -^ (RY)2P(O)SR'
11 (RY)2P(S)SH —*• (RY)2PSH + S
12 (RY)2PSH+ R'OH —»• (RY)2POR! + H2S
13 (RY)2PSH + R'OH —*• (RY)2PSR' + H2O
14 2(RY)2P(S)SH + 3C12 —»• 2(RY)2P(S)C1 + S2C12 + HC1
15 (RY),P(S)OH + (RY),P(S)C1 —* (RY)2P(S)OP(S)(YR)o + HC1
16 (RY)2P(0)SH + (RY)2P(S)Ci —^ (RY)2P(O)SP(S)(YR)2 + HCi
NH4OH
17 C2H5SH + CH2CH2 ^Q > C2H5SCH2CH2OH
O
18 NH3 + CH2CH2 —» H2NCH2CH2OH
>V::, O
19 CH2CH2 + H2O —^ HOCH2CH2OH
O
287
-------
TABLE B-17. (Continued)
Number Generalized Reaction'*)
20 C2H5SCH2CH2OH + CH2CH2 — •> C2H5SCH2CH2OCH2CH2OH
O
21 HOCH2CH2OH + CH2CH2 — *• HOCH2CH2OCH2CH2OH
\ /
O
22 2RSHI2L.RSSR
23 (C2H5O)2P(S)C1 + R"YH — »• (C2H5O)2P(S)OR"
24 (C2H5O)2P(S)C1 + H2NCH2CH2OH — » (C2H5O)2P(S)NHCH2CH2OH
[O]
25 (C2H50)2P(Y)YCH2CH2SC2H5 - ^(C2H5O)2P(Y)YCH2CH2SOC2H5
[O]
26 (C2H50)2P(Y)YCH2CH2SOC2H5 - -(C2H5O)2P(Y)YCH2CH2SO2C2H5
[O]
27 (C2H50)2P(S)OCH2CH2SC2H5— *• (C2H5O)2P(O)OCH2CH2SC2H5
28 (C2H50)2P(S)OCH2CH2SC2H5 + H2O — *• (C2H5O)2P(S)OH
+ C2H5OP(S)(OH)2
+ C2H5SCH2CH2OH
+ C2H5OH
29 (C2H50)2P(0)SCH2CH2SC2H5 + H2O — ^ (C2H5O)2P(O)SH
+ (C2H50)2P(Q)OH
+ C2H5SCH2CH2OH
+ C2H5SCH2CH2SH
(a) R and R' - alkyl or substituted alkyl
R" =
HOCH2CH2- or HOCHgCHgOCHjCHg-
Y = oxygen or sulfur.
288
-------
TABLE B-18. POSSIBLE CONTAMINANTS IN DEMETON
Number
1
2
3
4
5
t*
7
ti
9
10
11
12
13
14
IS
It,
17
18
IS
20
21
22
23
24
25
26
Contaminant
C2H5OH
P2S5
lC2H5O)2P(S)SH
(C2H5O)2P|S)SC2H5
(C^H^OIjPS
1C 2M5O)2P(S)OH
(C2H5OI2PlOISH
(C2H5OI2P(S)SP(S)(OC2H5)2
(C2H5Ol2P(S)SSPtS)(OC2H5»2
|C,H5OI2(C2H5S)PO
,C2H50.2PSH
.C2H3OI3P
(C2H5O)2tC2H5S»P
CI2
(C2H5OI2P(S)C1
(C2H50)2P(S)OPiSHOC2H5)2
(C.2H5O)^P(O)SP(SHOC2H5)2
C2H5SH
C,H2CH2
C2H5SCH2CH2OH
NHj
H2NCH2CH2OH
HOCH2CH2OH
C2H5SCH2CH2OCH2CH2OH
HOCH2CH2OCH2CH2OH
C2H5SSC2H5
Precursor**'
SM
SM
1 4 2
1 4 3
1 4 3
1 4 4
3
27
6
28
3
3
3
5
3
1 4 11
1 4 11
SM
3 4 14
6415
7415
SM
SM
18 4 19
27
Cat.
19 4 21
19
19 4 20
19 4 23
18
Reaction
Number(b>
--
--
1
2
3
4
5
28
6
29
7
8
9
10
11
12
13
--
14
15
16
--
--
17
28
--
18
19
20
21
22
Step
1
1
1
1
1
1
St
1
St
1
1
2
1
1
1
1
2
2
2
2
3
3
3
St
3
3
3
3
3
3
Likelihood of Being
Present in
Final Product' d'
0
0
0
4
4
+
4
0
+
0
0
0
4
0
4
44
44
0
0
44
0
0
0
4
0
0
289
-------
TABLE B-18. (Continued)
Number
27
28
29
30
31
32
33
34
35
3t
37
3b
39
40
41
42
43
44
45
4fc
47
Contaminant
(C2H50)2P(S)OCH2CH2SC2H5
(C2H5O12P(O)SCH2CH2SC2H5
lC2H5O)iC2H5S>P(O)OCH2CH2SC2H5
(C2H5O)2P(S)OCH2CH2OCH2CH2SC2H5
(C2H5O)2P(OISCH2CH2OCH2CH2SC2H5
(C2H5O)2P(S)OCH2CH2OH
i C2H5O)2P(S)OCH2CH2OCH2CH2OH
lC2H-O)2P(OISCH2CH2OH
(C2H5OI2P(S)NHCH2CH2OH
HSCH2CH2OH
C2H5C1
(C2H.OI2PlSISCH2CH2OH
(C2H-0)2PiS)OCH2CH2SOC2H5
,C2H.O»2P.S,OCH2CH2S02C2H5
,C2H.O,2PI0)SCH2CH2SOC2H5
,C,H50)2PlO)SCH2CH2S02C2H5
(C,H5C»2PlO)OCH2CH2SC2H5
C2H5OPlSHOH)2
4
4 or St
4
4
4
4
4
4
4
3A
3A
4
St
St
St
St
St
St
St
St
St
Likelihood of Being
Present in
Final Product
DEMETON
(mixture of
27 and 28)
4
4
4
0 '
0
0
0
+
0
4
4
4
4
4
4
4
4
+ " "r
4
lal Precursor refers lu the contaminant numbered in this table.
SM starting material
Cat. - ralalysl
«bl See Table B-17. ^ . . fc . „ . , ^. f
(cl The step (Figure B-10) during which the contaminant might be formed;
indicates possible formation during storage. *
(dl 0 likely to be present at levels below 1 ppm
4 likely to be present at levels above 1 ppm but below 100 ppm
44 likely to be present at levels above 100 ppm.
290
-------
Step 1 4 C2H5OH + P2S5 *2 (C2H5O)2P(S)SH + H2S
O, O-dimethyl
pho s phor odithioate
Step 2 (C2H50)2P(S)SH + C12 >-(C2H5O)2P(S)Cl + S2C12
O, O-dimethyl
chlorophosphorothioate
Step 3 CH7=CCHzCO + CzHsOH ^CHsCOCHzCOOCzHs
Lo-l
ketene dixner ethylacetoacetate
EtOH NH3
Step 4 (CH3)2CHCN *-(CH3)2CHC(NH)OC2H5 »(CH3)2CHC(NH)NH2
HC1
isobutyryl 2-methylpropionamidine
nitrile
CH3
StepS CH3COCH2COOC2H5 + (CH3)2CHC(NH)NH2 ** N
N
2 -isopropyl-4 -methyl
6 -hydroxypyr imidine
Step 6 (C2H50)2P(S)Ci
CuCl2
+ Vf^ ^J
(CH3)2CH-L JLoH Na2C03 (CH3)2CH-L JLoP(S)(OC2H5)2
^^ _. /"• »T ^^ ^^
DIAZINON
FIGURE B-H. SYNTHESIS OF DIAZINON
291
-------
TABLE B-19. REACTIONS OCCURRING DURING PRODUCTION AND STORAGE OF DIAZINON
Reaction
Number Generalized Reaction
1. 4ROH -I- P2S5 — *2(RO)2P(S)SH + H2S
2. (RY)2P(Y)SH + R'OH - »(RY)2P(Y)SRH H2O
3. (RY)2P(Y)SH + R'OH - *-(RY)2P(Y)OR' + H2S
4. (RY)2P(Y)SR + R'OH^=^(RY)2P(Y)OR' + RSH
5. (RY)2P(Y)OR - *(RY)2P(Y)SR
6. (RY)2P(Y)SH + H20 - »*(RY)2P(Y)OH -I- H2S
7. (RY)2P(S)OH3=^(RY)2P(O)SH
8. (RY)2P(Y)YH - »(RY)2P(Y)YP(Y)(RY)2 + H
10]
9. (RY)2P(Y)SH - ^(RY)2P(Y)SSP(Y)(RY)2
10. (R Y)2P(S)OR '.« - ^ (R Y)2P(O)SR '
11. (RY)2P(S)SH - *-(RY)2PSH -I- S
12. (RY)2PSH + R'OH - »^RY)2POR' + H2S
13. (RY)2PSH + R'OH - *(RY)2PSR' + H2O
14. (RY)2PSH - HRY)2P(S)SP(YR)2
»
15. (RY)2PSH -I- C12 - ^(RY)2P(S)SP(YR)2 + 2HC1
16. (RY)2P(S)SH + C12 - *(RY)2P(S)SSP(S)(YR)2 + 2HCI
17. (RY)2P(S)SSP(S)(YR)2 + 2C12 - ^2(RY)2P(S)Cl -I- S2C12
18. 2S2C12 + 2H2O - *SO2 + 4HC1 -I- S
[OJ
19. RSH - *RSSR
292
-------
TABLE B-19. (Continued)
Reaction
Number Generalized Reaction
20. CH2=CCH2CO + ROH - ^CH3COCH2COOR
L0J
21. CH2=CCH2CO + H2O - *-CH3COCH2COOH
LO-!
22. CH3COCH2COOH - ^CH3COCH3 + CO2
HC1
23. RCN + R'OH - **RC(NH)OR' + HC1
24. RC(NH)OR' + NH3 - »RC(NH)NH2 + R'OH
25. RC(NH)OR? + H2O - »-RCONH2 + R'OH
CH,
26. CH3COCH2COOR + R'C(NH)NH2
I I
-OH
27. CH3COCH2COOR + R'C(NH)NH2
28. (RY)2P(S)C1 + R'OH - MRY)2P(S)OR'
29. (RY)2P(S)C1 + NH3 - *(RY)2P(S)NH2
30. (RY)2P(S)C1 + R'C(NH)NH2 - MRY)2P(S)NHC(NH)R'
31. (RY)3P(Y) + R'OH - »-(RY)2P(Y)OR' RYH
32. (RY)2P(Y)C1 f Na2C03 - »-(RY)2P(Y)YNa
33. (RY)2P(Y)CH- (RY)2P(Y)YNa - >-(RY)2P(Y)YP(Y)(YR)2
[O]
34. (RY)3PS - -^(RY)3PO
35. (RY)3PY -f H20 - MRY)2P(Y)OH
293
-------
TABLE B-20. POSSIBLE CONTAMINANTS IN DIAZINON
K>
No.
1
2
3
4
5
6
7
'8
9
10
11
Contaminant
P2S5
(C2H50)2P(S)SH
(C2H50)2(C2H5S)PS
(C2H50)3PS
(C2H50)(C2H5S)2PS
(C2H50)(C2H5S)P(S)SH
(C2H50)2P(S)OH
(C2H50)2P(0)OH
(C2H50)(C2H5S)P(0)SH
(G2H50)2P(S)SP(S)(OC2H5)2
(C2H50)2P(S)SSP(S)(OC2H5)2
Precursor^3-)
SM
1
2
2
3
3
2
2
35
7
6
2
2
2
Reaction
Number
-------
TABLE B-20. (Continued)
No. Contaminant
13 (C2H50)3P
14 (C2H50)2(C2H5S)P
15 (C2H50)2P(S)SP(OC2H5)2
16 (C2H50)2(C2H5S)PO
17 (C2H50)3PO
jo 18 (CHS, ps
VO £• J J
Ul
19 (C2H50)(C2H5S)2PO
20 (C2H5S)3PO
21 (C2H50)2P(S)C1
22 (C2HgO)(C2H5S)P(S)Cl
23 S2C12
24 S
Precursor
12
12
12
12
4
9
16
5
3
5
11
6
11
23
Reaction
Number Final Product W
0
0
0
++
0
+
++
+
+
0
0
+
-------
TABLE B-20. (Continued)
No.
25
26
27
28
29
NJ
\0
* 30
31
32
33
Contaminant
CH^CCF^CO
CH3COCH2COOC2H5
CH3COCH2COOH
CH3COCH
(CH3)2CHCN
(CH3)2CHC(NH)NH2
(CH3)2CHCONH2
J&
N-£x\
(CHLLCHl^ JJ-OH
•5 *• ^i*.*^^
Precursor'*'
SM
25
25
27
SM
1
29
30
30
31+26
Reaction
Number^
—
20
21
22
23
24
25
26
Likelihood of
Being Present in
Step
-------
TABLE B-20. (Continued)
No.
Contaminant
Precursor^3-'
Reaction
Number^)
Likelihood of
Being Present in
Step
-------
TABLE B-20. (Continued)
No.
Contaminant
Precursor**'
Likelihood of
Reaction Being Present in
Number(b) Step(c) Final Product^)
38
33+22 28 6
39
35
34 6 or St
40
35+33 31
P(S)(OC2H5)
41
37
35
31
6
6
-------
TABLE B-20. (Continued)
Likelihood of
Reaction Being Present in
No. Contaminant Precursor^*) Number^) Step^c^ Final Product^
42 (C2H50)2P(S)ONa
43 (C2H50)2P(S)OP(S)(OC2H
44 CH3
N^ 71 (
(CH.CHL 0-SS-l
i dn. /_ v/rm-Vw J—o o —v.
32 \Nx^
45 C,H OH
£* «)
46 C,HeSH
ti D
47 C2H5SSC2H5
48 (C2H50)2P(S)NH2
49 (C2H50,2P(S)NHC(NH)CH
21 32
[ ) 42-f21 33
CH 41 19
^<^N
^CIi(caJz
35 35
36 35
46 19
21 29
(CH ) 21+31 30
6 +
6 +
6 0
6 or St +
6 or St +
6 or St +
6 +
6 ++
(•) Precursor refers to the contaminant numbered in this table. SM = starting material.
(b) Sec Table B-19 /
(c) The step (Figure B-ll) during which Che contaminant Bight be formed. St indicates possible formation during storage.
(d) 0 - Likely to be present only at levels below 1 ppm
4 = Likely to be present at levels above 1 ppm but below 100 ppm.
++ = Likely to be present at levels above 100 ppm.
-------
Step 1
Cl
©
benzene
3CI.
chlorine
Fed,
Cl
Cl
3HC1
1,2, 4-trichlorobenzene hydrogen
chloride
Step 3
Cl
1, 2, 4-trichloro-
benzene
NaOH
sodium
hydroxide
190 C
600 psi
OH
2, 5-dichlorophenol
NaCl
sodium
chloride
o
o
Step 3
Step 4
Cl
Cl
2, 5-dichlorophenol
3, 6-dichlorosalicyclic
acid
CO
potassium
2, 5-dichlorophenoxide
xylene
130-140 C
500 psi
NaOH
or
(CH3Cl)
methyl sulfate
or
(methyl chloride)
Cl
Cl
3, 6-dichlorosalicylic
acid
H2Q
NaOH
Cl
OCH,
Cl
methyl ester of
3, 6-dichloro-2-methoxy-
benzoic acid
(not separated)
3, 6-dichloro-
2-methoxybenzoic acid
(Dicamba)
CH3OH
methanol
FIGURE B-12. SYNTHESIS OF DICAMBA
-------
TABLE B-21. REACTIONS OCCURRING DURING PRODUCTION OF DICAMBA
Reaction
Number Generalized Reaction
1 ArH H- C12 FeCl3 r ArCl -f HCl
2 ArCi + NaOH - >-ArOH + NaCl
3 ArCl + ArOH NaOH» ArOAr' + NaCl
5 ArOH KOH» ArOK C°2 » Ar(QH)COOH
6 ArCOOH (CH3)2SO4) ArCOOCH
NaOH
7 ArOH (CH3)2S0^ ArOCH
NaOH
8 ArCOOCH + HO - >*ArCOOH + CH OH
301
-------
TABLE B-22. POSSIBLE CONTAMINANTS IN DICAMBA
No . Contaminant
1 Benzene
2 C6H5C1
3 C6H4C12
4 C6H3C13
5 C6H2C14
6 C6HC15
7 C6C16
8 CgH5OH
9 C6F4C10H
10 C6H3C12OH
11 C6H2C13OH
12 C6HC14OH
13 C.C1-OH
D J
14 C6H4(OH)2
15 C6H3C1(OH)2
16 C6H2C12(OH)2
17 C6HC13(OH)2
18 C6C14(OH)2
19 C1C6H4OC6H4C1
21 Cl C H OC H Cl
Pre-
cursor*
SM
1
2
3
4
5
6
2
3
4
5
6
7
9
10
11
12
13
3+9
4+9
10+3
4+10
Likelihood of Being
Reaction Present in Final
Number1* Stepc Product d
—
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
2
3
3
3
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
2
2
2
2
0
0
0
+
0
0
0
0
+
++
+
+
0
0
0
0
0
0
0
+
+
302
-------
TABLE B-22. (Continued)
No.
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
Contaminant
C13C6H20W1
C13C6H2°C6H3C12
C13C6H2OC6H2C13
CV6HOC6H3C12
C15C6OC6H3C12
Cl2-DBDe
Cl3-DBDe
Cl.-DBD6
C1C,H,(OH)COOH
O J
C12C6H2(OH)COOH
C13C6H(OH)COOH
C14C6(OH)COOH
C1C6H(OH)2COOH
C1C6H3(OH)COOCH3
C12C6H2(OH)COOCH3
Cl3CfiH(OF)COOCH3
C14C6(OH)COOCH3
C1C6H(OH)2COOCH3
C1C6H3(OCH3)COOCH3
Pre-
cursor*
5+9
11+3
5+10
11+4
5+11
6+10
12+4
7+10
13+4
9+11
10
10+11
10+12
11
9
10
11
12
15
30
31
32
33
34
35
Likelihood of Being
Reaction Present In Final
Number^ Stepc Product*1
3
3
3
3
3
4
4
4
5
5
5
5
5
6
6
6
6
6
7
2
2
2
2
2
2
2
2
3
3
3
3
3
4
4
4
4
4
4
0
+
0
0
0
of
0*
°£
+
•H-
+
0
0
0
0
0
0
0
+
303
-------
TABLE B-22. (Continued
No.
41
42
43
44
45
46
47
48
49
50
51
Contaminant
C12C6H2(OCH3)COOCH3
C13C6H(OCH3)COOCH3
C14C6(OCH3)COOCH3
ClCj.H(OH) \0(JH_ ) COOCHn
C1C£F (OCH, ) ,COOCH0
O J / J
C1C6H3(OCH3)COOH
C12C6H2(OCH3)COOH
C1,C,H(OCH_)COOH
JO J
C14C6(OCH3)COOH
C1C,H(OH)(OCH-)COOH
O J
C1C,H(OCH0)0COOH
O j f.
Pre-
cursor*
36
37
38
39
44
40
41
42
43
44
45
Likelihood of Being
Reaction Present in Final
Number** Stepc Product**
7
7
7
7
7
8
8
8
8
8
8
4
4
4
4
4
4
4
4
4
4
4
+f
+
0
0
0
•H-
DICAMBA
+f
+
0
+
a. Precursor refers to the contaminant numbered in this table. SM • starting
material. Solv. - solvent.
b. See Table B-21.'
c. The step (see Figure B-12) during which the contaminant might be formed.
d. 0 - likely to be present at levels below 1 ppm.
+ - likely to be present at levels above 1 ppm but below 100 ppm.
++ • likely to be present at levels above 100 ppm.
e. DBD - Dibenzo-p-dioxin
f. Analysis of dlcamba by E. A. Woolson, et. al. (J. Agr. and Food Chem. 20
(2), 351-354 (1972) showed <0.5 ppm of any one chlorodioxin in this
pesticide.
304
-------
Step 1. 4CH3OH
P2S5
2(CH30)2P(S)SH
.0,0-dimethyl
phosphorodithioate
Step 2.
C1CH2COOH +
chloroacetlc
acid
H
C1CH2COOCH3
methyl
chloroacetate
H20
Step 3. C1CH2COOCH3 +
methylamlne
ClCHjCONHCH.
N-methylchloroacetamlde
CH-OH
Step 4. (CH30)2P(S)SH + C1CH2CONHCH3
alkali or
tertiary
amine
•
solvent*
(CH30)2P(S)SCH2CONHCH3
0,0-dimethyl
S-(N-methyIcarbamoyImethy1)
phosphorodithioate
(Dimethoate)
^Solvents include: chloroform* methylene chloride, toluene, benzene, carbon
tetrachloride, and cyclohexanone.
FIGURE B-13. SYNTHESIS OF DIMETHOATE
305
-------
Alternative A
Step A-l. Same as Step 1.
Step A-2. Same as Step 2,
Step A-3.
(CH30)2P(S)SH
0,0-dimethyl
phosphorodithioate
C1CH2COOCH3
methyl
chloroacetate
(CH30)2P(S)SCH2COOCH3
0,0-dimethyl
S-(carbonic thoxyme thy 1)
phosphorodithioate
Step A-4. (CH30)2P(S)SCH2COOCH3 +
CH.OH
methylamine
(CH30)2P(S)SCH2CONHCH3
Dimethoate
methanol
Alternative B
Step B-l. Same as Step 1.
Step B-2.
(CH30)2P(S)SH
0,0-dimethyl
phosphorodithioate
C1CH2COOH
chloroacetic
acid
alkali
(CH30)2P(S)SCH2COOH
0,0-dimethyl
S-(carboxymethy1)
phosphorodithioate
Step B-3. (CH30)2P(S)SCH2COOfl +
CH3NCO
methyl
isocyanate
C6H-
(CH30)2P(S)SCH2CONHCH3
Dimethoate
benzene
FIGURE B-14. ALTERNATIVE SYNTHESES OF DIMETHOATE
306
-------
TABLE B-23. REACTIONS OCCURRING DURING PRODUCTION AND STORAGE OF DIMETHOATE
Reaction
Number
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
4ROH + PS
(RY)2P(Y)SH + R'OH
(RY)2P(Y)SH + R'OH
(RY)2P(Y)SR + R'OH
(RY)2P(Y)OR
(RO)2P(Y)SH
(RY)2P(Y)SH -1- H20
(RY)3PY + H20
(RY)2P(S)OH
2(RY)2P(Y)YH
2(RY)2P(Y)SH
(RY)2P(S)SH
(RY)2PSH + R'OH
(RY)2PSH + R'OH
2(RY)2PSH
(RY)2P(S)OR'
(RY)3PS
Cl CH,, .COOH + CH
x (3-x)
x " 1, 2, or 3
C1CH2COOCH + R"RMINH
C12CHCOOCH + R"Rm NH
C1CH2CONR"R" ' + R"Rm
CH,NHCH0CONR"R'" + C1CH
\
Generalized Reaction
^ 2(RO)2P(S)SH + H2S
* (RY)2P(Y)SR' + H20
*• (RY)2P(Y)OR' -I- H2S
> (RY)2P(Y)ORf + RSH
P»S
-=-2^ (RY)2P(Y)SR
P2S5
» (RO)(RS)P(Y)SH -h (RS)2P(Y)SH
>- (RY)2P(Y)OH -»- H2S
>• (RY)2P(Y)OH -H RYH
>• (RY)2P(0)SH
>- (RY)2P(Y)YP(Y)(RY)2 + H2Y
-&1+- (RY)2P(Y)SSP(Y)(RY)2
+• (RY)2PSH •«• S
>• (RY)2PORf -I- H2S
+• (RY) PSR' + H,0
[0]"
+ (RY)2P(S)SP(RY)2
7 » (RY)2(R'S)PO
-121*- (RY)3PO
3OH ^ ClxCH(3.x)COOCH3 + H20
>• ClCHjCONR''^" -»- CH CH
*• C12CHCONR"R'" + CH OH
NH +• R"R"IHCH2CONRIIR"1
«CONR"RHt *- CH,N (CH0CONR"RMI ) n
307
-------
TABLE B-23. (Continued)
Reaction
Number
Generalized Reaction
, »
23 (RY)2P(S)SH -I- C1CH2COZ
24 2(RY)2P(S)SH + C^CHCOZ
25 CH3OH + CICH.COZ
26 (CH30)2P(S)SCH2CONHCH3 -I-
alkali^ (RY)2P(S)SCH2COZ
alkali
[(RY>2P(S)S]2CHCOZ
OH
27 (CH30)2P(S)SCH2CONHCH3
28 HSCH2CONHCH -H HjO
29 2HSCH2COZ
30 (CH30)2P(S)SCH2COOCH3
HSCH^OOH +
[0]
OH
31
32
33
34
35
(a) R and
R"
R"1
Y
Z
C1CH2COOH + H20 +• HOCHgCOOH
OH"
T-™" O »^ •* f\ *^ \rti O ^^ O * V V A
CH3NCO + CH3NH2 >• CH3NHCONHCH3
(CH,0)0P(S)SCH0COOH 4- CH.NCO >• (CH_0)_P(S)SCH-CONHCH- + C0«
3 i i 3 32232
R1 «
K
K
•
alkyl
methyl
methyl or H
oxygen or sulfur
-NHCH , -N(CH3)2, -OH, or -OOU.
308
-------
TABLE B-24. POSSIBLE CONTAMINANTS IN DIMETHOATE
Number
1
2
3
4
5
6
7
o
\O
8
9
10
11
12
13
14
Contaminant
P2s5
CH3OH
(CH30)2P(S)SH
(CH30)2(CH3S)PS
(CH30)3PS
(GH30)(CH3S)2PS
(CH30)(CH3S)P(S)SH
(CH30)2P(S)OH
(CH30)2P(0)SH
(CH30)2P(0)OH
(CH30)(CH3S)P(0)SH
(CH3S)2P(S)SH
(CH30)2P(S)SP(S)(OCH3)2
(CH30) 2P(S)SSP(S) (OCH3) 2
(a)
Precursor
SM
SM
27
1+2
2 + 3
2+3
2 + 4
1+4
3
3
3
5
8
9
6
3
3
3
Reaction
Number
-------
TABLE B-24. (Continued)
Number
15
16
17
18
19
20
w 21
o
22
23
24
25
26
27
28
29
30
Contaminant
(CH30)2PSH
(CH30)3P
(CH30)2(CH3S)P
(CH30)2P(S)SP(OCH3)2
(CH30)2(CH3S)PO
(CH30)3PO
CH3SH
(CH3S)3PS
(CH3S)3PO
C1CH2COOH
C12CHCOOH
C13CCOOH
C1CH2COOCH3
C12CHCOOCH3
C13CCOOCH3
CH3NH2
Precursor
3
15
15
15
5
19
5
4
6 + 21
22
SM
Iflt-24
Im-24
2+24
2+25
2+26
SM
40
Reaction
Number (b)
12
13
14
15
16
4
17
4
4
17
—
—
—
18
18
18
27
Step(c)
1
1
1
1
1
• 1
1
1
1
2
—
—
2
2
2
3
St
Likelihood of
Being Present In
Final Product
-------
TABLE B-24. (Continued)
Number
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
Contaminant
(CH3)2NH
C1CH2CONHCH3
C12CHCONHCH_
CHjNHCH.CONHCH.
C1CH2CON(CH3)2
CH3NHCH2CO(NCH3)2
(CH3)2NCH2CONHCH3
(CH3)2NCH2CON(CH3)2
CH3N(CH2CONHCH3)2
(CH30) 2P(S) SCH2CONHCH3
(CH30) 2P(S)SCH2C(»(CH3) 2
(CH30)2P(S)SCH2COOH
(CH30)2P(S)SCH2COOCH3
(CH30) (CH3S)P(0)SCH2CONHCH3
(CH30) £P (0) SCH2CONHCH3
Precursor
Im-30
27 + 30
28 -1- 30
30 + 32
27 + 31
30 + 35
31 + 32
31 + 35
32 + 34
3 + 32
30 -I- 43
42 + 55
3-1-35
3 + 24
40
3 + 27
40
40
Reaction
Number
—
19
20
21
19
21
21
21
22
23
30
35
23
23
27
fH^® 0*4
16
17
Step
—
3
3
3
3
3
3
3
3
4
A-4
B-3
4
4 or B-2
St
4 or A-3
4 or St
St
Likelihood of
Being Present in
Pinal Product W)
0
++
+
+
*
0
0
0
0
Dimethoate
~
4+
+
++
+
-------
TABLE B-24. (Continued)
M«ber
46
47
48
49
50
51
52
H »
54
55
56
ContaBinant
(CH o) (CH s)p(s)sc&2cancH
[ (CH,O) .P(S) SI AGBCOBBCH
CH.OCH.CCRDCH.
HSCH2coracH3
RSCH.COOH
CH . HtOOCtt . S*»CH .lAirttiCH
HOCH COQH
Z
HOOOCii_OCll_OOOH
CHjno
CHJBCOsBCH.
Precursor
7 + 32
12 + 32
3 + 33
2 + 32
40
50
50
24
24 + 53
SM
55
Reaction
23
23
24
25
26
28
29
31
32
33 + 34
Step
4
4
4
4
St
St
St
B-2
B-2
B-3
B-3
Likelihood ol
r
Being Present in
Final Product^)
0
0
0
*
0
0
0
(a) Precursor refers to the «-*»»t-«»lT««fTf nusfcered in this table. SM * starting Material; Iat-24 - imparity
in Bo. 24; I»-30 - i^arlty in Bo. 30.
GO See Table B-23.
^c^ The stew (Figure W-l? nr.visare B-14) darlne which the cnntaKtaant «i«ht be formed. St Indicates possible
foraBtrlon daring storage.
(d) 0 - likely to be present only at levels below 1 pp*
+ * likely to.be present at levels above 1 ppn bat below 100 ppn
++ * likely to be present at levels above 100 ppsu
-------
Step 1
OH
phenol
CHjCH « CH CH3
mixture of
1 - butene and
2 - butene
A1(OC,
aluminum
phenolate
OH
CH
o- sec -butyl phenol
Step 2
OH
CH.
o-iec-butyl
phenol
HNO.
nitric
acid
• ulfurlc
acld
OH
CH2CH3
o-tec-butyl-4,6-
dlnltrophenol
(Ueed In the form of various
•alts with ammonia or
amlnee)
FIGURE B-15. SYNTHESIS OF DINOSEB
313
-------
TABLE B-25. REACTIONS OCCURRING DURING PRODUCTION OF DINOSEB
Reaction
Number Generalized Reaction
Al(OC,H )
1 ArOH + RR'C = CR"R'" - ° 3 » Ar(OH)CRR'CHR"R"1
Al(OC,H )
2 ArOH + RR'C = CR1^1" - 2_iJV ArOCRR'aHR'-R"1
HNO
ArH - i ArNO
H SO
4. ArH — = - ^ ArSO3H
ArOH + ArSO H
ArSO Ar
£*
ArOH
314
-------
TABLE B-26. POSSIBLE CONTAMINANTS IN DINOSEB
Number
1
2
3
4
5
0
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29 .
Contaminant^*'
C6H5OH
C4H8
Al(OC6H5)3
C4H9CfeH4OH
(C4H9>2C6H3°H
(C4H9>3C6H2OH
C6H5°C4H9
C4H9C6H4°C4H9
C4H9C6H3(N°2)OH
C4H9C6H2(N02)2OH
(C4H9)2Ct,H2(N°2)°H
C6H4(N°2)OC4H9
C6H3(N°2)2OC4H9
C4H9C6H3(N02,OC4H9
C4H9C6H2(N02)2OC4H9
C,HJNO,)OH
64 t
C6H3(N°2)2°H
C H (NO-LOH
o e. is
C4H9CfaH3(S03H)OH
C4H9CoH2(S03H,,N02)OH
(C4H9)2C6H2(S°3H)OH
CoH4(S03H)OC4H9
CW I C ^^ U \l ^ ^\ \f^f~ U
n \3 ^J n )\ iN v*_ i^x v n
O J J •» 49
C4H9CoH3(S03H,OC4H9
C4H9CfaH2(S03H)(N02)OC4H9
C H.tSO.H)OH
0 4 3
C H (SO.H)(NO,)OH
633 2
C6H2(S03H>(N02)2°H
HOC H(C H.)SO,C,H (C H_)OH
PTOur..r
-------
TABLE B-26. (Continued)
Number
Contaminant^0)
Reaction
Precursor(b) Number<«) Step(d>
Likelihood of
Being Present in
Final Product**)
30 HOC^H The step (see Figure B-15) during which the contaminant might be formed
(e) o J-ikeiy to oe present at levels below 1 ppm
+ Likely to be present at levels above 1 ppm but below 100 ppm
++ - Likely to be present at levels above 100 ppm.
316
-------
Step 1 4C2H5OH+ P2S5 *- 2(C2H5O)2P(S)SH + H2S
O, O-diethyl
phosphorodithioate
Step 2 (C2H5O)2P(S)SH-I-C12 MC2H5O)2P(S)C1 + HC1
O, O-diethyl
chlorophosphorothioate
Step 3 HoYoV+ (CH3)2SO+ HC1 *• HO-/Q V S+(CH3)2C1- + H2O
phenol dimethyl dimethyl 4-hydroxyphenyl
sulfoxide sulfonium chloride
Step 4 HO-/OV S'*'(CH3)2Cr 160"180 ^HO-\ Q> SCH3 + CH3C1
— \ f phenol \—f
4-(methylthio)
phenol
StepS (C2H50)2P(S)C1 + HO-O-SCH3 + Na2CO3 » (C2H5O)2P(S)O -osCH3 -I-
acetonV(C2H50)2P(S)0 ^OVSCH3 + N+C1
C02
O, O-diethyl-O-4-(methyl-
thio)phenyl phosphorothioate
Step 6 (C2H5O)2P(S)O-/Q V SCH3 -f H2O2 MC2H5O)2P(S)O-/O V SOCH
3
O, O-diethyl-O-4-(methyl-
sulfinyl) phenyl phos-
phorothioate (Fensulfothion)
FIGURE B-16. SYNTHESIS OF FENSULFOTHION
-------
Steps A1-A4 (Same as Steps 1-4, Figure 1)
Step A5 HO-/O \-SCH3 + (CH3CO)2O - *• CH3COO-^O VsCH3 + CH3COOH
4-(methylthio)
phenyl acetate
Step A6 CH3COO YoVsCH3 + H2O2 - *• CH3COO-^O VsOCH3 + HEO
4-(methylBulfinyl)
phenyl acetate
Step A7 CH3COO-osOCH3 + H2O - >-HO-OSOCH3 + CH3COOH
4-(methylsulfinyl)
phenol
I \ NaoCO^ r~~\
Step A8 (C2H50)2P(S)C1 + HO-/O-SOCH3 - = - ^ (C2H5O)2P(S)O--SOCH3
FIGURE B-17. ALTERNATE SYNTHESIS OF FENSULFOTH10N
• 318
-------
TABLE B-27. REACTIONS OCCURRING DURING PRODUCTION OF FENSULFOTHION
Number
Generalized Reaction'*'
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
4ROH 4 P2S5 » 2(RO)2P(S)SH + H2S
(RY)2P(V)SH 4 R'OH »• (RY)2P(Y)SR' + H2O
(RY)2P(Y)SH + R'OH >• (RY)2P(Y)OR' 4 H2S
(RY)2F(Y)SR4 R'OH*=t(RY)2P(Y)OR' 4 RSH
(RY)2P(Y)OR 5_5_(RY)2P(Y)SR
P,S.
(RO)2P(Y)SH £-2*- SCH3
(a) R and R* = alkyl, aryl or substituted aryl
R" = H, CH3S-, CH3SO- or CH3SO2
Rm = CH3CO-, (C2H50)2P(S)- or
Y = oxygen or lulfur.
x = 1 or 2.
319
-------
TABLE B-28. POSSIBLE CONTAMINANTS IN PENSULFOTHION
Number
1
2
3
4
5
<-
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
Contaminant
P2S5
C2H5OH
(C2H50»2P(S)SH
(C2H5Ol2(C2HsSlPS
(C2H5OI3PS
(C2H5Oi(C2H5Sl2PS
2P(OlOH
2P(S)SH
rC2H5O)2P(S 1SP1S )(OC2Hsl2
(C2H5O)2P(S)SSP(SHOC2Hs)2
(C2H5O)2PSH
(C2H50|3P
(C2HsO)2(C2H5S)P
(C2H5012P(S>P(OC2H512
(C2H5O)2(C2H5S)PO
rc2H5o.3po
C2H5SH
(C2H5SI3PS
(C2H5S)3PO
C12
(C2H5O)2P(SIC1
CfcHjOH
(CH3)2SO
Precursor'*'
SM
SM
38
1 + 2
2 + 3
2 + 3
2 + 4
1 * 4
3
3
5
38
8
9
6
3
3
3
3
3
IS
15
15
5
2 + 19
2+4
6 + 21
22
SM
3+24
SM
SM
Reaction
Number 'b>
--
8 + 27
1
2
3
4
5
6
7
8
8
9
7
8 + 9
6
10
11
12
13
14
15
16
17
4
4
4
18
--
19
--
--
Step's >
1
1
St
1
1
1
1
1
1
1
1
St
1
1
1
1
1
1
2
1
1
1
1
1
1
1
1
1
2
2
3
3
Probability of
Being Present
in Final
Product'*1
0
4
+
"
+4
*
*
4
0
0
0
0
4
++
0
0
0
0
+
0
0
0
0
0
++
++
*.
320
-------
TABLE B-28. (Continued)
Numbrr
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
Contaminant
[4-HOC6H4S(CH3l2] Cf
[2-HOC6H4S(CH3l2]' Cf
4 -HOC<,H4SCH3
2-HOC6H4SCH3
CH3C1
CH3COCH3
(C2HsO)2P(S)O -/pVsCH3
(C2H5OI2P(S)0 -/O^
H202
CH^COOH
(C2HsOl2P(S)O -/oVsOCHj
(C2H5OI2P{SIO-/O^
\__/
CH3SO
(CH3COI2O
4-CH3COOC£H4SCH3
2-CH3COOC6H4SCH3
4-CH3COOC6H4SOCH3
2-CH3COOC6H4SOCH3
4-HOQ,H4SOCH3
2-HOC6H4SOCH3
4-CH3COOC6H4SO2CH3
4-HOC<,H4SO2CH3
(C2H5012P(S)0-/OVS02CH3
^— ^
(C2H50)(C2H5S)P(O)O/OVSCH3
(C2H5O1(C2H5S)P(O)O «^>SOCH3
(C2H5OMC2H5S)P(0)0-/OVS02CH3
T—f
Precursor'''
26 4 27
26 4 27
28
29
28
Solv.
25 4 30
38
25 4 31
SM
Solv.
34 •» 36
25 4 45
35 4 36
25 4 46
SM
30 4 40
31 4 40
36 4 41
36 4 42
43
44
36 4 41
47
25 4 48
38
34
38
49
50
Reaction
Number'0'
20
20
21
21
21
--
22
26
22
_ .
23
22
23
22
--
24
24
23
23
25
25
23
25
22
26
17
17
17
23
Step'c'
3
3
4
4
4
5
5
St
5
6
A6
6
6
A8
6
A8
A5
AS
AS
A6
A6
A7
A7
A6
A7
AS
St
5
6 or St
6 or St
6
Probability of
Being Present
in Final
Product'*'
4
0
44
4
0
0
+4
4
0
0
Fensulfothion
+4
0
0
0
0
0
4-4
4
0
4
+ 4
•f
"
4
321
-------
TABLE B-28. (Continued)
Number Contaminant Precursor'*'
53 C2H5OI>S(OHt2 8
54 ll3P
St
St
St
5
5
Probability of
Being Present
in Final
Product'*1.*
4
4
44
44
(d i Precursor refers to the contaminant numbered in this table. SM = starting material; Solv. = solvent.
(bi Soc Table B-27.
)f, -The «tep (Figure B-16 or Figure B-171 during which the contaminant might be zoned, tsible
St Indicates possible•formation during storage
fd' u probably present only at levels below 1 ppm.
probably present at levels above 1 ppm but below 100 ppm.
- - - probably present at levels above 100 ppm.
322
-------
step)
on
m-cresol
2S°
Dimethyl
Sulfoxidc
11C1
15-20 C
OH
CH3
(C)I3)2S4C1-
dimclhyl (2-methyl-4-hydroj«y
phcrvyl) sulfonium chloride
CH.
(CH3)2s+cr
160-180 C
CH
CH,
CH3Cl
methyl chloride
3-methyl- 4- (methylthio)
phenol
Step 2
4 CH3OH +
2 (CH3O)2 P(S)SH +
JO, O-dimethylphos -
phorodithioic acid
Step 3 (CH3O)2 P(S)SH 4
(CH3O)2 P(S)C1 -I- HCl
O,O- dimethyl thio-
phosphoryl chloride
Step 4 ICH3O)2 P(S)Cl +
CH,
SCH,
KOH,
CH,
C6H6
FENTH1ON
FIGURE B-18, SYST11KSTS OF FENTUION
323
-------
TABLE B-29. REACTIONS OCCURRING DURING PRODUCTION ON FENTHION
Reaction
Number
Generalized Reaction**'
|
C H.tOH)(CHJlS
CiH2(OH)|CH3)2lS(CH3)2Cr]
C H.tOHHCH.) + Z(CH->,SO
u -4 3 3 t
C,H,(OH)(CH.)| S(CH,), Cl"]
O «v 3 SC
C H.(OH)(CH.)|S(CH,),Cr]
03 3 3 t
C,H,(OH)(H.)(SCH.),
O t 3 32
4ROH
2(RO)2P(S)SH
ROP(SHSH)
(RV)2P(Y)SH + R'OH
(RY)2P(Y)SR' + H2
R'OH
(RY)2P(Y)OR'
10
(RY)2P(Y)SR t R'OH
(RY>2P(Y)OR' + RSH
1 1
ZRSH
RSSR
12
(RY)2P(Y)OR
(RY)2P(Y)SR
(RY )2P|Y)SH
(RY)2P(Y)OH + H S
14
(RY)2PiSIOH
(RY!2P(O)SH
2(RY)2P
-------
TABLE B-29. (Continued)
Reaction
Number
Generalized Reaction
(a)
21
2 P(Y)SH 4
(RY)2P(Y)Cl
(RY)2PlS>OH 4
(RY)2P(S)C1 4 HC1
30
(RY)2P(0)SH4
(RY)2PiO)Cl4
31
(RY) PSH 4 Cl
(RY)2PC1 4
32
IRY) P(Y)OH 4 CL
(RY)2P(Y)CM HCl
33 (RY)P(S)(SH)24
RY P(S)C12 4
(RY)P(0)tSH)24
RYP(0)C124
ROM 4
ROSSR 4 HCl
3o
(RY»2P(S)CI 4 R"OH
(RY)2P(S)(OR")4 NaCl
37
(RYI P(Y)Cl 4 R"OH
(RY)2P(Y)OR"+ NaCl
38 (RY)2P(O)C14 R"OH
(RY)2P(0)OR"+ NaCl
39 (RY)2PC1 4 R"OH
(RY)2POR"4 NaCl
40
(RY)P(S)C12+ 2R"OH
RYP(S)(OR")2 + NaCl
325
-------
TABLE B-29. (Continued)
Reaction
Number
Generalized Reaction
, ,
41
(RYJP(O)Cl, + R"OH
i
RY P(O)(OR"), + NaCl
i
42 S2C12 + 2R"OH
R"O-S-S-O-R" + NaCl
43
50
(RYl P(0)(SR")(OR") + H.O
(RY),P(O)(OH), + RSH + R"OH
it*
51 (RY),POR"+HO - »• (RY).POH-f R"OH
i i i
52 R"OH + SC1 - - R"OSSOR" + NaCl
53
R"SH 4 S Cl
RSSSSR" + NaCl
54
ROSSOR" + HO
2R"OH
55
R"SSSSR" + HO
2RSH + S
56
R"SH
R"SSR
57
(RY),P(S)OC6H4(SCH3)(CH3)
f.
(RY),P(S)OC.H (SOCHJ(CHJ
58
(RY)2P(S)OC6H4(SCH3»(CH3)
59 (RY)2P(S)OC6H4SOCH3 + H2
(RY)2P(S)OH
60
(RY)P(S)OH + HOC6H4(SO2CH3)(CH3)
326
-------
TABLE B-29. (Continued)
Reaction
Number
Generalized Reaction
bl (RY)2F<0)SC6H4SCH3
62
o3
(RY>2P(O)OH + HSC H
(RY>2P(O)OH
(RY).PtOIOC H,(SCH.)ICH.)
c t> 4 J J
.^,
6433
(RY),PiO)OC^H.(SOCH,)(CHJ+ H,O
£. o4JJ£
(RY),P(O)OH + HOC,H.(SOCH-)(CH,)
08
(RYiPlO)OC H.JSO.CH.MCH.) + H,O
2 O4233Z
(RY),P(O)OH + HOC.H .(SO,CH,)(CH,)
Z o 4 t J J
o9
RY P(S)(OC H ,(SCH,)(CH,) + H.O
t> 4 3 3 £
RY P(S)OH + HOC.H .(CH,)(SCH.)
o 4 3 j
70
(CH.SI(CH.)C H.YH
3 J O J
(CH,SO)(CH.)C .H.YH
J J D J
71
(CH.S)(CH,)CtH.YH
3 3 b J
(CH.SO,)(CH.)C,H YH
j t J o i
72
(a I H and R' = alky] or substituted alkyl
Y = O or S
R" - 3-methyl-4-methyltWophenyl.
327
-------
TABLE B-30. POSSIBLE CONTAMINANTS IN FENTHION
No.
1
2
3
•1
>
O
1
a
9
10
11
12
13
14
15
lo
17
18
19
C ontami na nt( • '
C H.tCH HOH)
o 4 3
CH3SOCH3
"* ~1
C H,(CH )(OH)|S(CH.)*cri ,
•> 2 3 32 '2
C H.iCH^lOH)
o 3 32
C H,iCH.),(OH)|S2P(S)SH
MeOPlSKSH)
(MeO) PS
(MeO)2(MeS)PS
(MeO)(MeS)2PS
(MeO)(MeS)P(S)SH
Precuraor'^
SM
SM
,42
142
SM
542
542
3
4
6
7
SM
SM
12413
12413
12413
14413
17
14
Reaction
Number <«>
1
1
1
5
3
3
3
2
6
4
4
7
7
7
7
7
12
12
23
Step")
1
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
Likelihood of
Being Preaent
in Final
Product'6'
0
0
0
0
0
0
0
4
0
0
0
0
0
4
4
44
0
0
0
328
-------
TABLE B-30. (Continued)
No.
20
21
22
23
24
25
2o
27
28
29
30
31
32
33
34
35
3to
37
30
Contaminant'*'
(MeO)2P(S)OH
(MeO)2P(O)SH
(MeO) PlOlOH
(MeO)(MeS)PtO)OH
(MeS)2PlS)SH
*
(MeO»2PtS)SPlS)(OMe)2
(MeO) P(S)SSP(S)lOMe)2
lMeO)2PSH
(MeOj^P
(MeO)2(MeS)PO
(MeO) PO
(MeS)3PS
(MeS)PO
(MeO)2P(S)SP(OMe)2
)MeO)2(MeS)PO
(MeO)(MeS)2PO '
(MeO)2(MeS)PO
MeSH
MeSSMe
Precursor^0'
14
20
21
19
19
14
14
14
26
26
16
16
30
26
16
18
17
35
37
Reaction
Number
-------
TABLE B-30. (Continued)
No.
39
40
41
42
43
44
45
4o
47
48
49
50
51
52
53
54
55
56
57
Contaminant'3'
(MeO)2P(S)Cl
(MeO)P|S)Cl2
(MeOltMeS)PlSlCI
(MeO)2P(0)Cl
(MeOKMeS)P(CMCl
(Meb)2P|S»Cl
(MeO)PCl
ICH SUCH 1C H OP(S)(OMe)2
(CH,S),tCH )C H,OP(S)(OMe),
3 i 3 O i t-
'CH^CH^C^OPfSHOMe*
(CH,S),tCH.),C HOPlSKOMrU
3 i 3 £. O &
1 (CH,S)(CH,)C H,O) ,P(S)lOMe)
1 3 3 o 3 '2
|(CH.S),(CH.)C H,O] ,P(S)lOMe)
3 c. 3 O t. £•
I tCHSKCHJ.C H.Ol .PlSKOMel
3 3 i 6 i £•
I (CH.S»,tCHJ,C HO),P(S)(OMe)
3 i 3 £ O £
(CH S)(CH )C HO PlSKOMeltSMe)
(CH.S),(CH.)C,H,O P(S)(OMe)(SMe)
32 3 o t
(CH.SKCHJ.C H,O P(S)(OMe)(SMe)
3 3 i b i
(CH.SMCHJ.C HO P(S)(OMe)(SMe|
3 £• 3 i o
Precunor(b)
14+20
15
19
21+22
22
23
26
38+8
38+9
38+10
38+11
39+8
39+9
39+10
39+11
40+8
40+9
40+10
40+11
Reaction
Number'0*
Zb, 32
33
28
30
30
26
31
36
36
36
36
40
40
40
40
37
. 37
37
37
Step
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
4
4
Likelihood of
Being Present
in Final
Product'*)
*
0
0
0
0
0
0
Fenthion
*
0
0
-
0
0
0
*
0
0
0
330
-------
TABLE B-30. (Continued)
No.
58
59
bO
bl
-
b3
b4
o5
Ob
b~
b8
b9
70
71
72
73
74
75
76
Contaminant'9'
(CH S)(CH,»C H,O P(O)(OMe)
3363 2
|CH3S>I2 Product***
4 ++
4 0
4 0
4 0
4 +
4 0
4 0
4
4 +
4 0
4 0
4 0
4 0
4 0
4 0
4 0
4 +
4 0
4 0
331
-------
TABLE B-30. (Continued)
No.
Contaminant
Likelihood of
Being Present
Reaction in Final
Precursor'0' Number'0' Step'd' Product'"'
77
-------
Step 1
^V^ ^s ^
oloj - to
CH.
CH.
catalyst
naphthalene
o-xylene
^ ^>
o
?
X
Step 2
\
phthalic
anhydride
NH3
ammonia
200-220 C
^^ ^
O
I
\
HH
phthal,imide
Step 3 2CS
5C1
2CC13SC1
carbon chlorine
disulfide
trichloromethane-
sulfenyl chloride
S2ci2
sulfur
nonochloride
Step 4
9
C
X
NH
phthalimide
CC13SC1
^ ^
O
NSCC13 + NaCl
trichloromethane- FOLPET
sulfenyl chloride
FIGURE B-19. MAIN REACTIONS IN THE PREPARATION OF FOLPET
333
-------
TABLE B-31. REACTIONS IN PRODUCTION AND STORAGE OF FOLPET
Reaction
Number
Generalized Reaction
3
4
5
7
8
9
10
(RCO)20 + H20
(RCO)20 + NH3
2NH + NH3
2 RCOOH
RCOOH
2 RCONH,
RCOOH + NH
+
'2
:i
csci
3
2
2 + C12
3C1,
2S2C12
2H20
-»• RCONH.
H,
2 + S2C12
•CClgSCl
2H20
3S + 4HC1 + SO
_9
CH C
II >
CH-CX
4HC1
334
-------
TABLE B-31 (Continued)
Reaction
Number Generalized Reaction
11
12
13
14
15
16
17
18
19
20
21.
22
23
24
25
26
27
28
4CC13SC1 F<*- S2C12 4- 2CC14 4- CC13SSCC13
3" 2 4 ' U2C 2
CCJ-qbLJ. T H~O * CC1— SOU T HCl
L>VjX«i5un T n— vj » v/vjn TOT jiii_,x
CC1 SOH 4- CC1 SCI .9 *. CCl SOSCC1
3" 3 *" 3° 2" 3 3° 3
CC1,S09SCC1. + HO — CC1,SO,H 4- CC1.SH
J £ J fc J J J
NaOH >
PPI *?P1 4- ^RPO^ NH "T ..fc. fRPO^ N<5rCl
3 A / J
PPI ^n PI 4- fRpfi1} NH ^-^fi?po^ TJ^O rn
J Z / Z / J
PCPl -4« /T7PA^ MW ^ ^TTPfl^ TCfPCM^Pm?^
UbL>X~ ~ livUU/ nMU. •— ^» IJWjU/ ~1N^5W \. \j\Jt\l _
i L if.
/T)prt^ WIT 4. c PI ^ fTTpri\ viccvt frno\
(K\J(J) nMll T D«l«Xn ^^*^vKl»UJ«NoJ>mt/UK^-
^ fc *. ^ *>
r*P1 CP1 -L UPITr-PUlJ ^ TT ^PPI CNPIIPTIPITJ
Lt>JL_bL>J- T IvUll'-wluv ^•^tUv/LXnO JLllUlll/XK
3 J
RCrl"HL'Hlv 4* Ov«XMbuf|\«X "^~^^ A\viHv^Xv(ixvwwX« • OV/M
•3 • « «5 w
^TfPrt^ WCPP1 4- IT n •! t'Of%f\\ MH 4» PPI flOTJ
iKuujnJNaiAiX.) T n_u • ^KV>U/ >nti T uLiX-bvjn
2 3 e. i J
roi
^nro^ M^CCI — — .«» fRCO^ NSO cci
2 3 i i J
(RCO)2NH 4- 2CC13SC1 (RCO)2NC1 4- CC13SSCC13 4- HCl
RCONH2 4- 2CC13SC1 RCONHC1 4- CC13SSCC13 4- HCl
335
-------
TABLE B-32. POSSIBLE CONTAMINANTS IN FOLPET
No.
Contaminant
Reaction
Precursor Number Step
Likelihood of Being
Present in Final
Product
"
SM
un
4. II
CH-
\ 1
-r
/\
5' (§1 C/° '
6. HOOCCH-CHCOOH 4
x
'• (^
x
\.COOH
)T
^x^c0011
X^COOH
'• (QlcOKH '
^^
^
^ ^
9
'• (PI }" *«
X^ .X^ n X
i
2
2
3
3
4
6
4
25
1
1
1
1
1 or 4
1 or 4
2
2
2
St
336
-------
TABLE B-32. (Continued)
Ho . Contaminant
/^com2
W' LQJ-com2
11. HOOCCH-CHCONH2
0
12. II NlH
—8
13. H2NOCCH-CHCONH2
14. CS2
15. CSC12
16. S0C10
2 2
17. CC13SC1
18. CCl-SO-Cl
3 2
19. S
20. CC13SSCC13
21. CC13SOH
22. CCl.SOSCCl,
3 3
23. CC13S02SCC13
24. CC1.SO.H
Precursor
9
8
4
6
11
12
11
SH
14
14
17
17
15
15
16
21
17
22
17
26
21+17
22
23
18
Reaction
Number
5
6
4
6
4
5
6
—
7
7
11
12
8
9
10
14
11
16
13
25
15 '
16
17
18
Likelihood of Being
Present In Final
Step Product
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
4 or St
3
4 or St
4
4 or St
4
4
4
4
0
+
0
0
0
0
+
0
-H-
+
0
0
+
+
337
-------
TABLE B-32 (Continued)
No.
25.
26.
27.
28.
29.
30.
31.
32.
Reaction
Contaminant Precursor Number Step
CC13SH 23 17 4
^\x C1
|O T NSCC13 9+17 19 4
9
CH-C
II NSCC1, 12+17 . 19 4
/ 3
CH-C,
(ol!>2-3 r s :-.
0
CH-fr
|| NSO.CC1, 12+18 20 4
CH-J-
IX—N. iT" \ ^ T/^N I
11 NCSN ( ) 9+15 21 4
L^-^JL ^ JL^-^J
0 0
_9 9^
^^U ^^ w wD
|| NCSN' H 12+15 21 4
CH-CX ^C-CE
0 0
9 P ^-^
CH-CN xc-tvvi
|| NCSN ( ) 9+12+15 21 4
" _ / \. ^ -L^— * j
0 0 ^^^
Likelihood of Being
Present in Final
Product
+
FOLPET
++
-
+
+
0
0
338
-------
TABLE B-32. (Continued)
No.
Contaminant
Likelihood of Being
Reaction Present in Final
Precursor Number Step Product
33.
X S
NSSN
/ X
^ ^
O
9+16
22
y 9
CH-CX ,C~CR
34. || XNSSN ||
CH-C C-CH
0
12+16
22 4
P,
CH-L .
35. || NSSN
-
9+12+15 22 4
ci.csc
-c
36. | NH
clc-
&
12+17
23 4
C1.CSC-_V
37. 3 | ^
cic-
27+17
36+17
23
19
4
4
Cl-CSC- C
38. | NSO,CC1,
cic-r ^ J
29+17
23
39. HOOCCH (SCC13) CHC1CCOH
40. HOOCCH(SCC13)CHC1CONH2
41. H2NOCCR(SCC13)CI!C1CONH2
6+17
11+17
13+17
23
23
23
4
4
4
0
0
0
339
-------
TABLE B-32. (Continued)'
No.
Contaminant
Precursor
Reaction
Number Step
Likelihood of Being
Present in Final
Product
A3.
44
45
ci3cc-cx
42. I ^NH
cic--
9
NSCC1-
HOOCCOOH
HOOCCONH
46 H2NOCCONH2
47 HOOCCONHC1
12-1-18
24
27+18
42+17
1
3
44
45
45
24
19
1
2
4
4
28
4
4
1
1
2
2
4
48
0
II
CH-C
NCI
CH-
NCI
12
27
27
a. Precursor refers to the contaminant numbered in this table. SM - starting material.
b. See Table B-31.
c. The step (Figure B-19) during which the contaminant might be formed. St indicares
possible formation during storage.
d. 0 - likely present only at levels below 1 ppm.
+ = likely present at levels above 1 ppm but below 100 ppm.
++ = likely present at levels above 100 ppm.
340
-------
Step 1 ACHjOH
methanol
and
Step 3a
or
and
+ P2S5
phosphorus
pentasulfide
0,0-dimethyl hydrogen
phosphorodithioate sulfide
Step 2a II
CH-
r
+ 2C2H5OH
maleic
anhydride
CHCOOC.H-
CHCOOC2H5
diethyl
naleate
ethanol
CHCOOC.H,
•*• II 2 5
CHCOOC2H5
diethyl
oaleate
(CH30)2P(S)SH (C2H5)3N^ (CH30>2P(S)SCHCOOC2Hf
0,0-dimethyl
phosphorodithioate
CH-?X
Step 2b II (.
CH-
maleic
anhydride
•r (CH30)2P(S)SH
0,0-dimethyl
phosphorodithioate
(CH 0),P(S)SCK-CN
Step 3b J * I JO
0,0-dimethylphosphorodithioyl
auccinic anhydride
MALATHION
9
(CH«0),P(S)SCH-C
0,0-dinethylphosphorodithioyl
auccinic anhydride
+ 2C2H5OH +- (CH30) 2P (S) SCHCOOC2H5
ethanol
MALATHION
FIGURE B-20. SYNTHESIS OF MALATHION
341
-------
TABLE B-33. REACTIONS OCCURRING DURING PRODUCTION OF MALATHION
Reaction
Number Generalized Reaction?
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
Awntj J. T> o ^- n fnn\ T>^c^ou j_ n c
/p_v\ p /v\ en 4. p * OP fc fw\ V fv\ v^ i> fv\ on -L. U'AD ^^_^_^ ft>v\ T>^V\AI>* J.
(RY)0P(Y)SR + R'OH y ^ (RV) P(Y)OR' +
2 /
/ /
ZfPVN TfY^YTI fc TPY^ V fV\*TP (V\ (W\ J
2fRY^ PfY^SH fc (RY^ P^Y^SSP(Y^ (RY^
CRYj PlS)OR rf ^ iRYj^PfOISR
^T>v^ v^c^oii *- /i»v% T>CH j. e
^^^v^ T>GTJ x u * nn ^__^_^ /^>v^ T>nv * j. u c
(RY)2PSH + R'OH ^-(RY)2PSR' + H20
7 (WY} T*rTT *• •* fc fBY^ P^^^^P^YR^
/PY% pv 4- P n > ^nv^ p^v^^H 4- PVTJ
fpv-\ p«s _ L9i fvy\ pn
rsro^ n + p.*nn ^ Brnfln + Rrnop.1
(PY) . P (Y) SH + -CH-CH- 5Z — ^ (RY) .P (Y) SCI
foi
?T?*?H l J fc R'J'SR
prnnp * 4- p."np > ppnnn" 4- u'np.
/PY\ p /y\ on 4. P ' on > f PY^ P ^Y^ ^np * ^
t, i
H2S
RSH
S
ICH2-
+ ROH
a. R - alkyl or substituted alkyl group; Y - oxygen or sulfur.
342
-------
TABLE B-34. POSSIBLE CONTAMINANTS IN MALATHION
No.
.— — •
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
Contaminant
Vs
CH3OH
(CH30)2P(S)SH
(CH30)2(CH3S)PS
(CH30)3P6
(CH30)(CH3S)2PS
(CH30)(CH3S)P(S)SH
(CH,0),P(S)OH
3 Z
(CH30)2P(0)SH
(CH30)2P(0)OH
(CH30)(CH3S)P(0)SH
(CH3S)2P(S)SH
(CH30)2P(S)SP(S) (OCH3)2
(CH30) 2P (S) SSP (S) (OCH3) 2
(CH30)2PSH
f^Tt rt\ O
\»****^y •»*
(CH30)2(CH3S)P
(CH30)2P(S)SP(OCH3)2
(CH30)2(CH3S)PO
Pre-
cursor*
SM
SM
1+2
3+2
3+2
4
6
H
4
3
j
3
3
5
30
8
9
7
7
/
7
3
3
3
15
15
15
5
Likelihood of Being
Reaction Present in Final
Number^ Stepc Product*1
—
—
1
2
3
4
5
^
4
5
j
4
6
15
15
7
6
7
5
4
8
9
11
12
13
14
10
1
1
1
1
1
1
i
X
1
1
X
1
1
1
St
1 or St
1 or St
1
1
1
1
1
1
1
1
1
1
0
+
+*
+*
**
+
+
+
0
o
+
0
0
0
0
0
+
343
-------
TABLE B-34. (Continued)
Pre-
No . Contaminant cursor8
20 (CH.O)-PO
21 (CH3S)3PS
0
CH-fc
22 || V0
oo r v na
£.0 L_n_un
CHCOOH
24 ||
CHCOOC.H.
25 || 2 5
CHCOOC2H5
CHCOOH
26 ||
CHCOOH
(CH,0)J»(S)S(
27 3 T
(
19
5
6
SM
SM
22+23
24+23
24
22
\> 3+22
u
(CH_0)(,P(S)SCHCOOC,HI. 3+24
28 3 Z * * 27+23
CH2COOH
(CH,0),P(S)S(
29 3 Z
:HCOOH 3+24
27+23
Reaction
Numberb
4
16
4
"
—
17
18
18
18
19
19
17
19
17
Likelihood c
Present in
Stepc Product
1 0
1 0
2a,2b ++
2a,3b +
2a +
2a ++
2a +
2a
2b ++
3a ++
3b
3a ++
3b
CH2COOC2H5
(CH,0),P(S)S<
30 J z
:HCOOC,H, 28+23
3 29+23
CH2COOC2H5 3+25
(CH 0),P(S)SCHCCOH 3+26
31 J z
28
CH COOH 29
18
18
19
19
18
18
3b MALATHIC
3b
3a
2b +
32
4
4
344
-------
TABLE B-34. (Continued)
No.
33
oc
35
36
37
38
39
An
HU
/ «
41
42
Al
H J
Contaminant
0
CH3SCH-CS
«X-jj'°
CH,SCHCOOC,H,
J i Z 3
1
CH2COOH
CH.SCHCOOH
1
CH3SCHCOOC2H5
CH0COOC-H-
2 25
CH.SCHCOOH
CH2COOH
H2S
HSCH~CV
-------
TABLE B-34. (Continued)
Mo.
Contaminant
Likelihood of Being
Pre- Reaction Present in Final
cursor* Number** Stepc Product*
C0H,OOCCHSCHCOOC0H,.
44 Z 5 | \ Z w
42+25
21 3a
45
32
23 3a,2b
46
CH-SSCHCOOC.HC
3 , 25
CHjCOOCjH-
C0HCOOCCHSSCHCOOC0H,
47 * 5 | I 2 5
(CH,0),P(S)SCHCOOC0H_
48 3 * | 2 5
32+42
42
30+2
23 3a,2b
23 3a,3b
24 3a,3b
49
(CH-0)>P(S)SCHCOOCH,
J / i -j
yv^n-v
50 J
(CH.O) (C0H.O)P(S)SCHCOOC9Hc
51 3^5 | Z 5
30+2
30+23
24 3a,3b
CH.COOCjH.
1CHCOOCH,
1 3
CH2COOCH3
48+2
49+2
24
24
3a,3b
3a,3b
25 3a,3b
(CH_0)(CH,S)P(S)SCHCOOC-H.
52 3 3 ! 25
7+25
19 3a
53
(CH3S)2P(S)SCHCOOC2H5
CH
12+25
19 3a
54
,P(S)SCHCOOC0H,
I 2S
51+23
25 3a,3b
346
-------
TABLE B-34. (Continued)
No.
Contaminant
Likelihood of Being
Pre- Reaction Present in Final
cursor* Numberb Stepc Productd
(CH,o) ,P (o) SCHCOOC.HC
55 3 2 I 2 5
CH.COOCjH.
56 (C2H5)3N
30 16 St -»-
Cat 19 3a +
a. Precursor refers to the contaminant numbered in this table. SM - starting material.
b. See Table B-33.
c. The step (Figure B-20) during which the contaminant might be formed. St indicates
possible formation during storage.
d. 0 - likely present only at levels below 1 ppm.
+ - likely present at levels above 1 ppm but below 100 ppm.
++ - likely present at levels above 100 ppm.
347
-------
Step 1
CH3CHO
acetaldehyde
NH2OH
hydroxylamine
CH3CH-NOH
acetaldehyde oxime
Step 2
CH3CH-NOH
acetaldehyde
oxime
C12
chlorine
OMF
dimethy1-
formamlde
CH3C(C1)»NOH + HC1
N-hydroxyethanimidoyl hydrogen
chloride chloride
Step 3
CH3C(C1)-NOH
N-hydroxyethan-
imidoyl chloride
CH3SH
methyl
mercaptan
NaOH
sodium
hydroxide
CH3C(SCH3)-NOH
methyl N-hydroxy-
ethanimidothioate
Step 4
CH3C(SCH3) + NOH
methyl-N-hydroxy-
ethanimidothioate
CH3NCO
methyl
isocyanate
(C2H5)3N
triethyl
amine
CH3C(SCH3)-NOCONHCH3
methyl N-[[(methylamino) •
carbonyljoxy] ethan-
imidothioate
(me thorny 1)
FIGURE B-21. SYNTHESIS OF METHOMYL
348
-------
TABLE B-35. REACTIONS OCCURRING DURING PRODUCTION AND STORAGE OF METHOMYL
Reaction
Number
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
Reaction
CH3CHO + NH2OH *- CH3CH-NOH + EJ3
DMF
CH CH-NOH + Pi fc m pfri^Miarni 4. UPI
CH3C(C1)-NOH £ CH3CH(C1)NO , C1L CH3CC12NO + HC1
CH3C(C1)-NOH + C12 »- CH2C1C(C1)-NOH + HC1
CH3C(C1)-NOH -I- H20 -»- [CH3C(OH)-NOH] — *- C^CONHOH + HC1
raCl,C^Cl^•NOH + H O » en P1POHHOH
CTCfCl^«NOH + CH SH NaOH __ p/gpn )«NOH + NaCl
2CH SH I"] «n cgfjn
m nrrn^^NQH + CH SH » CH cicfscn ^«NOH
raClC^^l^«NOH + 2CH SH NaOH p., _pg CfSCH )-NOH
NflOT)
CH3NCO + H20 »- [CH3NHCOOH] *- ^3^2 + C°2
0
/\
irn wrn ^ CH - N N — CH^
A/s
CH3
CH3C(SCH3)-NOH + CH3NCO »- CH3C(SCH3)-NOCOHHCH3
349
-------
TABLE B-35. (Continued)
Reaction
Number
Reaction
18
19
20
21
22
23
24
CH3NCO + CH3SH
CH3CH=NOH + CHJJCO
CH3C(SCH3)-NOCOHHCH3
CH3C(SOCH3)-NOCONHCH3
CH3C(SCH3)-NOCONHCH3
CH.C(SCH.)-NOH + H.O
•j j &
CH3CONHOH
CHSH + [CHC(OH)-NOH] — ^
NHjOH
CH,CONHOH
J
350
-------
TABLE B-36. POSSIBLE CONTAMINANTS IN METHOMYL
Number
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
Contaminant
CH3CHO
NH2OH
CH3CH-NOH
C12
(CH3)2NCHO
(DMF)
CH3C(C1)-NOH
CH3CC12NO
CH2C1CH-NOH
CH2C1C(C1)-NOH
CH3CONHOH
CH2C1CONHOH
CH3SH
CH3C(SCH3)-NOH
CH3SSCH3
CH2C1C(SCH.)-NOH
CH3SCH2C (SCH3) -NOH
CH3SCH2CONHOH
CH3NCO
(C2H5)3N
CH3NH2
Precursor (a)
SM
10
SM
1 + 2
SM
Solv.
3 + 4
4 + 6
3 + 4
4 + 6
6
23
9
SM
23
6 + 12
23
12
9 + 12
9 + 12
11 + 12
SM
Cat.
18
23
Likelihood of
Reaction Being Present in
Number (b) Step(c) Final Product (d)
24
—
1
—
2
2
3
4
5
6
22, 23
7
22, 23
8
22
9
10
11
12
—
—
13
22
1
St
1
1
2
." 2
2
2
2
2
3
St
3
3
St
3
St
3
3
3
3
4
4
4
St
0
0
0
0
0
0
0
0
0
**
0
+
+*
+
0
0
0
0
0
*
351
-------
TABLE B-36. (Continued)
Number
21
Contaminant Precursor '*'
0
1
/\
CH_ - N N - CH0 18
3 | I 3
Reaction
.Number vb>
14
Likelihood of
Being Present in
Step*0' Final Product W
4 -H-
22
23
24
25
26
27
28
29
CH3NHCONHCH3
CH3C (SCH3)-NOCONHCH3
CH,C (Cl)-NOCONHCH,
J J
CH3NHCOSCH3
CH3CH-NOCONHCH3
CH3C (SOCH3)-NOCONHCH3
CH.C (S00CH. ) -NOCONHCH-
J / J J
CH-COOH
18
13
+ 20
+ 18
6 + 18
12
+ 18
3 + 18
23
27
10
15
16
17
18
19
20
21
24
4
4
4
4
4
St
St
St
+
Methomyl
++
+
•»
0
0
0
(a) Precursor refers to the contaminant numbered in this table.
SM - starting material; Solv. - solvent; Cat. - catalyst.
(b) See Table B-35.
(c) The step (Figure B-21) during which the contaminant might be formed.
St. indicates possible formation during storage.
(d) 0 - likely to be present at levels below 1 ppm
+ - likely to be present at levels above 1 ppm but below 100 ppm
-H- » likely to be present at levels above 100 ppm.
352
-------
Step 1.
4ROH
methanol phosphorus
or pent as xil fide
ethanol
2(RO)2 P(S)SH
O,O- dialkyl
phosphorodi-
thioate
H2S
hydrogen
sulfide
Step 2. (R0)2 P(S)SH
Step 3.
Step 5.
Cl,
O
Step 4. Cl
benzene
<£>
Cl,
(RO)2 P(S)C1
O,O- dialkyl
chlorophos-
phorothioate
* ci-/O\
HNO3
NaOH
\ /
chlorobenzene
•NO;
\—S
p-nitrochloro-
benzene
^NaO-( O VNO
\_/
sodium p-nitro-
phenoxide
Step 6. (RO)2 P(S)C1 + NaO
/O\
s2ci2
sulfur
monochloride
N0
(RO)2
NO-
Methyl Parathion (R = CH3)
Parathion (R = CJt)
FIGURE B-22.
MAIN REACTIONS IN THE PREPARATION OF
'METHYL PARATHION AND PARATHION
353
-------
TABLE B-37, REACTIONS OCCURRING DURING PRODUCTiai
OF PARATHION AND METHYL PARATHION
Reaction
Number
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
Generalized Reaction^'
r.
11011 '2"5 * " 2 " " ' 2~
/ P> "V \ T>/ "V \C T_T J D 1 /^\T_T •- ' *"* V \ T5/ V \f\ D ! 4. TJ C
2 2 Z
P2S5
/ n \r \ -Q/ -tr \ ^ D *^ ^ / o T7" \ "D/ V \C D
L £,
1 17 V \ T>/V\c;T-T4. TI O h 1 R V \ T>^ V^OTT 4- TT CI
2 2
(RY)_P(Y)YII >• (RY) P(Y)YP(Y)(RY) + H_Y
2 2 22
t^V\ 'P/V^'?T-T — i— i- b. /RV^ 'P^V^'5'P/V W R V \
£• 2 <-
(RY) P(S)OR -* 9 (RY) P(O)SR
/ fj "\f \ T^yO! T T •! TJ ' ^^ T T W / TJ ^^ \ T3^^ I? ' J> U* ^!
2 22
/ O V \ TOO T_T _L O t /^ TT *^ / TJ v \ T>C O t J T_T J^
I IV 1 1 —STJll T JLV. vy 1 1 ^ I IX I I _ r^O IV T Xi_ W
2 22
[o]
2 22
22 22
\ -tv X y — i \O 70 A 1 T OX^ ^ ^ IV ^ / o *^\*^ f&& ±\ij ) \ J, XV/M » "JTlv^X
L L d. 2
2 22 2 22
(a) R = alkyl or aryl group; Ar = aryl group; Y = oxygen or sulfur.
354
-------
TABLE B-37. (Continued)
Reaction
Number
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
2S2C1
ArH •
ArH •
ArCl
ArCl
ArCl
2^
^
(RY)2
(RY)2
(RY)3
(RY),
(RY)2
(RY)3
(RY)3
DCTJ .
Korl •
Generalized Reaction*4'
2 + 2H2O *• SO + 4HC1 + S
C12
HNO3
Na°H> ArONa ^ * ArOII
ROH ^ ArUK T rid
^ONa ^^0^^
Ti/-ir\/-»A . A — OTS.IT *- /PV W A i-Ol"Pf Y^O A i- + RONa
•mr i A -<^kTiT- ^. IO"V\ "PfV \VNTa + A T-OR
PY + ArONa r v*^-* "7 ' ' «.rwix
P(Y)C1+ (RY)2P(Y)YNa * (RY)2P(Y)YP(Y)(YR)2 + NaCl"
_.,_-._. . ni^TT ^ /DV^ /OR^PY 4- 'HTII
P(Y)C1 T ROH * (i\.i )y\\JK.)n. T nv-.i
TJC "• •* — / P Y ^ T3^
f^b * vJK.1 J-^*-'
•mr i TT ("\ k. /RY\ "P/Y^OW+ RYH
[0] Reop
(a) R = alkyl or aryl group; Ar = aryl group; Y = oxygen or sulfur.
355
-------
TABLE B-38. POSSIBLE CONTAMINANTS IN PARATHION AND METHYL PARATH10N
Nu.
,
2
3
•t
••
I
'
C
«
10
1 1
1J
13
»
If
lu
17
Ih
,,
20
21
22
21
24
2i
20
27
2b
29
30
31
32
33
ConUmmant1*'
P,S
2 5
(RO)2P(SISH
(ROilRSIPS
2
l«Ol PS
i
(ROM Rsl, Pi
(KOllRSIPiSISH
(RCli. PiGlOH
lHOl,PiO)SH
.KO.lR&lPiOISH
(HO) P(SISPlSHOR)
lKOl,r<&ISSP(i>)lOKI,
"
|ROI,PSH
(ROijP
IROI IRSIP
iRO),PlSISP(ORI2
(ROl.(RS)PO
2
IHOIPO
3
,RO,,P(h,C.
(ROIiKSIPlSlCI
iROl.PlOlCI
(ROMHSIPlOlCI
s2c.2
s
C H
it i.
CtH5CI
C6H4CI2
C H (NO ICI
b -4 2
CoH3tN02'2C1
C^H^NO^C^
CoH2lN02)2C12
C H (OHlCl
b 4
C H (NO,K3H
O 4 2
C0H3|N°2'2°H
Precursor'^'
SM
1
2
19
2
3
18
3
2
7
2
ti
2
2
2
2
12
12
12
12
4
9
21
16
20
11
6
8
9
11
22
SM
24
25
24
27
26
29
2o
27
48
28
Reaction
Number'cl
- .
1
2
29
3
4
29
5
b
b
u + 7
o+ 7
9
10
16
11
12
13
14
IS
10
3
29
4
29
17
16+ 17
lb+ 17
16+ 17
17
18
--
19
19
20
20
20
20
21
21
31
21
Stcp«»
1
1
1
6
I
1
b
1
1
1
)
1
1
I
2
1
1
1
1
2
1
1
6
1
6
2
Z
2
I
2
2
3
3
3
4
4
'4
4
5
5
St
5
Likelihood of
Being Present in
Final Product* »
o
o
*-
*4
*«
o
o
o
o
-
++
o
«
*
o
+4
+4
o
o
o
o
o
++
o
o
0
+
o
o
0
o
++
«
356
-------
TABLE 1-38. (Continued)
No.
34
35
36
37
38
39
40
41
42
43
44
*5
46
47
48
49
SO
51
52
53
54
55
56
57
58
59
60
U
Conumtnaot<*>
C6Hj(N02)(OHK:i
C6H2
5
5
5
5
5
5
6
6
6
6
6
6
6
6
6
6
6
St
6
6 or Si
6 or SI
St
Si
St
St
St
SI
Likelihood of
Being Preseet la
Flaal Product!*'
o
0
+
o
o
o
o
o
o
o
++
+
o
.
Farathlon or
Methyl Parathion
»
o
*
++
+4
++
+
O
*
*
«*
*
*
(•) R « CHj or €2115
(M Precursor refer* lo Uw coaUminint numbered ia Ihii uble. SM > itartinf milerUl.
M! IV? .'tep "(Figl're B-22) during which the contaminant .ight be formed. St indicate, po.aible formation
during *tor««e.
(•) • • llkrly present onlv et level* below 1 ppm
+ « likely preeenl it levels above I ppm but below 100 ppm
++ • likely present at level* above 100 ppm.
357
-------
HNO
PCNB
FIGURE B-23. SYNTHESIS OF PCNB
358 '
-------
TABLE B-39. POSSIBLE CONTAMINANTS IN PCNB
No.
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
Contaminant
Benzene
Chlorobenzene
Dichlorobenzenes (3 isomere)
Trichlorobenzenes (3 isomers)
Tetrachlorobenzenes (3 isomers)
Pen tachlorobenzene
Hexachlorobenzene
Nitrobenzene
m-Dinitrobenzene
Chloronitrobenzenes (3 isomers)
Dichloronitrobenzenes (6 isomers)
Trichloronitrobenzenes (6 isomers)
Tetrachloronitrobenzenes (3 isomers)
Chloro-m-dinitrobenzenes (3 isomers)
Dichloro-m-dinitrobenzenes (4 isomers)
Trichloro-m-dinitrobenzene
Tetrachloro-ra-dinitrobenzene
Pentachlorobenzenesulfonic acid
Tetrachloronitrobenzenesulfonic acid
Octachlorodibenzodioxin
Precursor *a>
SMd
1
2
3
4
5
6
1
8
2
8
3
10
4
11
5
12
9
10
11
14
12
13
16
6
e
5
1 Formation Likelihood of being (c)
Step(b> Present in Final Product
la/2a,3a 0
la/2a,3b 0
lb,la/2a,2c,3b 0
lb,la/2a,2c,3b 0
lb,2c,3b +
lb,2c,3b ++
lb,2c,3b -H-
2b,3a 0
2b,3« 0
2b 0
3b
2b 0
2c,3b
lc,2b, +
2c,3b
Ic +f
2c,3b
2c,3b 0
2b
2b +
2c,3b
lc,2b +
2c,3b
Ic -H-
2c,3b
Ic +
e +
lb 0
359
-------
TABLE B-39 . (Continued)
No.
21
22
23
24
25
26
27
28
29
a.
b.
c.
Contaminant
Octachlorodibenzofuran
Decachlorobiphenyl
Octachlorobiphenylene
Hexachlorodinitrodihenzodioxin
Hexachlorodinitrodibenzofuran
Octachlorodinitrobiphenyl
Hexachlorodinitrobiphenylene
Decachlorodiphenyl ether
Octachlorodini trodiphenyl ether
Contaminant listed in this table.
Refers to the various steps of the
0 = Likely present only at levels
Precursor ^a'
5
6
5
16
16
17
16
6
17
three methods given
below 1 ppm
Formation
Step(b)
Ib
Ib
Ib
2c,3b
2c,3b
2c,3b
2c,3b
Ib
2c,3b
in Figure
Likelihood of
Present in Final
+
+
0
0
+
•f
0
0
0
B-23.
being (c)
Product
+ - Likely present at levels above 1 ppm but below 100 ppm
++ = Likely present at levels above 100 ppm.
d. Starting material.
e. Formed by various sequences of reactions in methods 2 and 3.
360
-------
Step 1
2(C2H502)P(S)SH
H2S
ethanol
phosphorus
pentasulfide
O,O-diethyl phosphoro-
dithioate
hydrogen
sulfide
Step 2 (C2H50)2P(S)SH
HCHO
O,O-diethyl
phosphor odithioate
formaldehyde
O, O-diethyl-S-(hydroxymethyl)
phosphorodithioate (not isolated)
Step 3 (C,HeO),P(S)SCH,OH
' L D L C
C,H,SH
c> 3
50 C
O, O-diethyl-S-(hyroxymethyl) ethyl
phosphorodiethioate mercaptan
O, O-diethyl-S-(ethylthiomethyl)
phosphorodithiodte
PHORATE
H2°
water
PIGOPE B-24. SYOTHESIS OF PHORATE
-------
TABLE B- 40. REACTIONS OCCURRING DURING PRODUCTION OF PHORATE
Reaction
Number
Generalized Reaction*
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
4ROH
2(RO)2P(S)SH
'+H20
(RY)2P(S)OH
•(RY)2P(0)SH
2'
+ H2Y
*• •*
,PSH
*• •*
i-"-i
H20
+ H,
,P(Y)SH +
+
,OH
,OH + RSH
2P(Y)SCH2
+ RSH
2P(Y)SCH2OH + ROH
-CRY)
+ H20
+ H2S
+ H20
23
24
25
26
27
28
RSH + CtUU -4—
RSCH2OH + RSH
RSCHjOH + RSH
RSR ^ fcRSOI
R"OR [°] > R°C
CO],R«
~
— r RSCHgUH
fc u pp n ep x n A
^RSCH-OR + n_5
I
)2R
;R
a. R - alkyl or substituted alkyl; Y - 0 or S
362
-------
TABLE B- 41. POSSIBLE CONTAMINANTS IN PHORATE
No.
1
2
3
4
5
J
6
7
8
9
10
11
12
13
14
15
16
17
Contaminant
P2s5
C2H5OH
(C2H50)2P(S)SH
(C2H50)2(C2R5S)PS
253
(C2H50)(C2H5S)2PS
-------
TABLE B-41 . (Continued)
No . Contaminant
18 (C2H50)2P(S)SP(OC2H5)2
19 (C2H50)2(C2H5S)PO
20 CC2W0
21 (C2H5S)3PS
22 (C2H5S)3PO
23 (C2H50)(C2H5S)2PO
0 It. ^ W CW
25 C2H5SSC2H5
26 (C2H50)2P(S)SCH2OH
27 (C0HC0)(C0H-S)P(S)SCH.OH
2525 Z
28 (C2H50)2P(S)SCH2SC2H5
29 (C2H50)(C2H5S)P(S)SCH2SC2H5
30 (C2H50)2P(S)SCH2OC2H5
31 (C2H50)(C2H5S)P(S)SCH2OC2H5
32 F(C2H50)2P(S)SCH2]20
33 [(C2H50)2P(S)S]2CH2
34 (C2H50)2P(S)SCH2OP(S)OC2H5)2
35 C H SCH OH
Pre-
cursor*
15
5
19
5
6
21
6
SM
24
3
7
26+24
27+24
26+24
27+24
26
26+3
26+3
24
Reaction
Number^
14
10
4
15
4
15
15
—
28
19
19
20
20
21
21
22
2
3
23
Likelihood 01
Present in 1
Step0 Product*
1 0
1 +
1 0
1 0
1 0
1 0
3 0
3 +
2t i
^^w
2 +
3 PRORATE
3^^§
T^
3.LI
TV
3 +
2 +
2 +
2 +
3 0
364
-------
TABLE B-41. (Continued)
No. Contaminant
36 Cjyaycp,
37 C2H5SCH2OC2H5
38 . See Table B-40.
c. The step (Figure B-24) during which the contaminant might be formed; St indicates
possible formation during storage.
d- 0 - likely to be present at levels below 1 ppm.
+ - likely to be present at levels above 1 ppm but below 100 ppm.
++ - likely to be present at levels above 100 ppm.
365
-------
|| I
N^ .N
^•{-"^
0
Cl
cyanuric
chloride
C2HcNH2
ethyl
amine
2°C
NaOH or
HO + solvent
Cl
2,4-dichloro
6 -ethylamino
5-triazine
+ C2H5NH2
40°C
NaOH or
H2O + solvent
Cl
Simazine
FIGURE B-25. SYNTHESIS OF SIMAZINE
366
-------
TABLE B-42. REACTIONS OCCURRING DURING SIMAZINE PRODUCTION
Reaction
No. Generalized Reaction^
OH
1 RC1 + R'R"NH »RNR'R"
2 RCi + H2O °H > ROH
3 ^C = N- + H2O *• ^C = O + -NH2
4 ^C = N-+ R'R"NH ^^c =
OH"
5 RCl + RNHR' > R2NR'
(a) R = a substituted 1,3,5-triazlne group; R' and R" = C2Hs or H.
367
-------
TABLE B-43. POSSIBLE CONTAMINANTS IN SIMAZINE
No.
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
-
C2H5NH2
(C2H5)2NH
NH3
Z-C^
0
N
Y
X=
Cl
Cl
Cl
C2H5NH
Cl
Cl
(C2H5)2N
Cl
Cl
NH2
Cl
Cl
Contaminant
Precur-
Reaction
Number
-------
TABLE B-43. (Continued)
No.
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
"V -• -
(C2H5)2N
NH2
Cl
NHZ
(C2H5)2N
NH2
C2H5NH
(C2H5)2H
Cl
Cl
OH
Cl
OH
OH
Cl
OH
OH
Cl
OH
OH
Contaminant
Y=
C2H5NH
C2H5NH
NH2
(C2H5)2N
(C2H5)2N
(C2H5)2N
NH2
NH2
Cl
OH
OH
OH
OH
C2H5NH
OH
OH
(C2H5)2N
OH
OH
NH2
Z=
C2H5NH
C2H5NH
(C2H5)2N
C2H5NH
C2H5NH
(C2H5)2N
NH2
NH2
OH
OH
OH
C2H5NH
C2H5NH
C2H5NH
(C2H5)2N
(C2H5)2N
(C2H5)2N
NH2
NH2
NH2
Precur-
sorfc)
6 + 2
6 + 3
8 + 3
14+3
14 + 2
9 + 3
12 + 1
12 + 2
4
24
25
5
27
6
8
31
9
11
33
12
Reaction
Number
-------
TABLE B-.43. (Continued)
Precur-
No. Contaminant sor'a'
36 OH (C2H5)2N C2HsNH 14
37 OH
38 OH
NH2 C2H5NH 15
NH2 (C2H5)2N 18
39 C2H5NHCON=C(NHC2H5)N=C(NHC2H5)NH2
6
40 C2H5NHCON=C(NHC2H5)NH2 39
41 C2H5NHCONH2 39
42 NH2CONH2 15
43 (C2H5)2NCONH2 14
44 C2H5NHC(=NC2H5)NH2 6
45 NH2C(=NC2H5)NH2 15
+ 1
+ 1
46 (C2H5)2NC(=NC2H5)NH2 14 + 1
-
47 C2H5NH-
-
N
CX C- NC2H5 6
N ^N
1
ci J2
+ 5
Reaction
Number O5)
2
2
2
3
3
3
3
3
4
4
4
5
Likelihood of
Being Present
in Final
Product^)
o
0
0
0
+
+
+
+
+
o
o
+
(a) Precursor refers to the contaminant numbered in this table.
(b) See Table U*42.
(c) 0 = likely present only at levels below 1 ppm
+ = likely present at levels above 1 ppm but below 100 ppm
++ = likely present at levels above 100 ppm.
370
-------
Step 1
Cl
NH2 + COC12
Cl
NCO + HC1
p-chloroaniline
phosgene
p-chlorophenyl
isocyanate
Step 2
Cl
NCO + (CH3)2 NH
NHCON(CH3>2
p-chlorophenyl
isocyanate
dimethylamine N'-(p-chlorophenyl)-N,N-
dimethylurea
(Monuron)
FIGURE B-26. SYNTHESIS OF MONURON
371
-------
Alternate A
Step A-l
(CH3)2NH
dimethylamine
COC12
phosgene
(CH3)2NCOC1 + HC1
dimethylcarbamoyl chloride
Step A-2
Step B-l
(CH3)2NCOC1
p-chloroaniline dimethylcarbamoyl
chloride
Alternate B
NH2'HC1 + NH2CONH2
Cl Jr\ \ NHCON (CH3) 2
H onuron
ICONH2 + NH4C1
p-chloroanlline
hydrochloride
urea
p-chlorophenylurea
Step B-2
1-/Q V NHCONH2 + (CH3)2NH
cAo
NHCON(CH3)2
p-chlorophenylurea dimethyl*- o-dichloro-
amlne benzene
FIGURE B-27. ALTERNATE SYNTHESES OF MDNURON
M onuron
372
-------
TABLE B-44. REACTIONS OCCURRING DURING PRODUCTION OF MONURON
Number
1
2
3
4
5
6
7
8
9
10
11
12
13
14
Generalized Reaction
RNHCOC1 ^ RNCO + HC1
RNHCOC1 + RNH2 > RNHCONHR
t . i
WMPn J. B_ftTU ^ DTJUPrtKTD..
BNfn 4- HoO N RTJH« i POi
R2NH + COC12 > R2NCOC1 + HCl
RNH2 + R2NCOC1 n > RNHCONR2 + HCl
i . i i ^_
RNH2 ' ,HC1 + NH2CONH2 > RNHCONH2
(a)
RNHCONH2 + R2OT ^ RNHCONR2 + NH3
RNHCONR2 + H20 ^ RNH2 + R2NH + C
ClXQ\.NHCON(CH3)2 UV. light ^
r1_/^ViNHCON(CH-,)-, * Hi" UV light',
ta^OVNHCON(CH3>2 uv i1**
02
y Q\JIHCON(CH3)2 + HCl
> HO/O)^"1001^01^2 "*" HC1
feotolysis products
including:
4-ClC6H4NHCON (CHO) CH3
4-C1C6H4NHCONHCHO
4-ClC6H4NHCONHCH3
4-ClCtHANHCONH2
4-ClCfiH4NHCONHC$H4Cl -4
4-ClC6H4NH2
4-ClC6H4NHCHO
4-C1 -2 -OH-C6H3NHCON (CH3) 2
(a) R * aryl or methyl.
R' = hydrogen or methyl
373
-------
TABLE B-45. POSSIBLE CONTAMINANTS IN MONURON
Number Contaminant
1 P-C^
2 COC12
3 0-C1C6H2NH2
4 m-ClC6H4NH2
5 p-ClC6H4N02
6 o-ClC6H4N02
7 p-C!C6H4NCO
8 o-ClC6H4NCO
9 m-ClC6H4NCO
10 Z,3-Cl2C6H3mi
11 2.5-Cl2C6H3NH
12 3,4-Cl2C6H3HH2 ^
13 2,4,5-Cl3C6H2NH2
14 4^1C6H4NHCONHC6%^
Precursor
SM
7
21
SM
Im-1
Im-1
Im-1
Im-1
1+2
2+3
2+4
Im-1
* I"-1
f'^N Im-1
'v,,'. Im-1
1+2
21
Reaction
Number
5
11
—
—
—
—
—
1+2
1+2
1+2
—
—
—
—
1+3
14
Step(c>
1
2
St
1
—
—
—
—
1
1
1
~
—
~
—
1
St
Likelihood of
Being Present
in Final Product
+*
0
+
0
+
0
0
0
0
0
0
0
0
+*
-------
TABLE B-45. (Continued)
Ul
Number
15
16
17
18
19
20
21
22
23
24
25
26
Contaminant
2-ClC6H4NHCONHC6H4Cl-2
2-C1C6H4NHCONHC6H4C1-4
3 , 4-Cl2C6H3NHCONHC6H4Cl -4
(CH3)2NH
CH3NB2
NH3
4 -C1C6B4NHCON (CH3) 2
4-C1C6H4NBCONHCH3
4-ClC6H4NHCONH2
2 -C1C6H4NHCON (CH3 ) 2
2^1C6^NHCONHCH3
2-ClC6H4NHCONH2
Precursor
2+3
1+2+3
1+2+12
SH
21
Im-18
Im-18
7+18
1+30
18+23
7+19
21
7+20
1+33
21
8+18
8+19
8+20
3+33
Reaction
Number (b)
1+3
1+3
1+3
11
—
—
4
7
10
4
14
4
9
14
4
4
4
9
Likelihood of
xv Being Present
Step^ ' in Final Product (d'
1 0
1 +
1 0
2 +
St
0
0
2 Monuron
A-2
B-2
2 ++
St
2 +
B-l
St
2 ++
2 0
2 0
B-l
-------
TABLE B-4S (Continued)
Number
27
28
29
30
31
32
33
34
35
36
37
38
39
40
Contaminant
3-ClC6H4NHCON (CH3)2
(C2H5)3N
C5H5N
(CH3)2NCOC1
(CH3)2NCON(CH3)2
(CH3)2NCOMHCH3
NH2COMH2
0-C6H4C12
C6H5NHCON(CH3)2
4-OH-C6H4NHCON (CH3) 2
4-ClC6H4NH-CON (CHO)CH3
4-ClC6H4NHCONHCHO
4-ClC<0l4NHCHO
ci^Q\jSHcoii(CH3)2
Precursor
9+18
Cat.
Cat.
2+18
2+18
19+30
SM
Sol.
21
21
21
21
21
21
Reaction
Number (b)
4
~
—
6
8
7
—
—
12
13
14
14
14
14
Ste»(C)
2
2
2 or A-2
A-l
A-l
A-l
B-l
B-2
St
St
St
St
St
St
Likelihood of
Being Present
in Final Product^ '
0
0
0
0
+
0
+
+
0
0
0
0
0
0
Footnotes appear on the following page.
-------
Footnotes for Table B-.45.
(a) Precursor refers to the contaminant numbered in this table
SM=starting material
Cat.= catalyst
Sol.= solvent
Im-l» impurity in No. 1
Im-18=impurity in No. 18
(b) See Table B-44.
(c) The step (Fig. B-26 or Fig. B-27) during which the contaminant
might be formed. St indicates possible formation during
storage.
(d) o=likely to be present only at levels above 1 ppm
+olikely to be present only at levels above "l ppm
but below 100 ppm
+4=likely to be present at levels above 100 ppm
377
-------
Step 1
Step 2
Step 3
o
Cl.
Toluene
COOH
+• HNO
Ci
p-Chlorotoluene
COOH
p-Chlorobenzoic Acid
COOH
4-Chloro-3,5-Dinitrobenzoic Acid
Rccry'd ETOH
COOH
Step 4
Step 5
SF/
Sulfur Tetraf luoride
+ NH(C3H7)2
Diisopropylamine
CF,
4-Chloro-3,5-Dinitrobenzotri-
fluoride
Recry'd-hexane-benzene
[3
1
+ Pr2N.HCl
H7C3X"%C3H7
Trifluralln
FIGURE B-28. SYNTHESIS OF IRIFLURALIN
378
-------
TABLE B-46. REACTIONS OCCURRING DURING PRODUCTION OF TRIFLURALIN
Reaction
Number
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
Generalized Reaction
ArH + C12 •• ArCl + HCl
ArCH3 +. C12 *• ArCH2Cl + HCl
ArfH^flH i •* - ArPMO.
ArH HN°3 to. ArNOo
ArrH-»OH _±L_te. ArCHnF
A Wun oB It. ^ Ai-PUT7.
SF
ArPOfYH oc It. ^ ArPfTP
SF '
ArCOOH ._ . -4 to- ArCF3
ArCL + RR'NH *- ArNRR1
A^PH.PI j. BP'NH to. AT*CH«NTIR'
ArCOF + HNRR ^ AruuwKK
OTJ'MTJ a. «Y ^ PP'NH»H5T
irf
ArCl + ROn m AruK
ArNRR1 • [hvl *• ArNHR
^^___ 1 11" 1 .^ * ^wm
""2 i \s °H
Pr-™ ^C2H5
r^CN hv _ (r^l
379
-------
TABLE B-47. POSSIBLE CONTAMINANTS IN TRIFLURALIN
No
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
Contaminant^8'
Toluene
C6H4
-------
IABLE B-47. (Continued)
No.
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
Contaminant**'
C6H(N02)2(COOH)C12
C6H2(N02) (CH2OH)C12
C6H(N02)2(CH2OH)C12
C6H2(N02)(CHO)C12
C6H(N02)2(CHO)C12
C6H(N02) (COOH)C13
C6(N02)2(COOH)C13
C6H(N02) (CH2OH)C13
C6(N02)2(CH2OH)C13
C6H(N02)(CHO)C13
C6(N02)2(CHO)C13
C6H4(N02)CH2OH
Cfp3(V02)2m2m
C6H2(N02)3CH2OH
C6H4(N02)CHO
C6H3(N02)2CHO
C6H^(N02)COOH
C6H3(N02)2COOH
C6H3(N02)(COF)C1
C6H3(N02)(CF3)C1
C6H2(N02)2(COF)C1
C6H2(N02)2(CF3)C1
C6H3(N02)(CH2F)C1
Precursor
11
9
9
10
10
14
14
12
12
13
13
15
15
15
16
16
17
17
18
18
19
19
20
Reaction (c)
Number
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
9
10
9
10
7
Step
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
Likelihood of Being
Present in . .
Final Product*6'
+
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
+
0
•H-
0
381
-------
TABLE B-47. (Continued)
No.
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
(a)
Contaminant
C6H2(N02)2(CH2F)C1
C6H3(N02)(CHF2)C1
C6H2(N02)2(CHF2)C1
C6H2(N02)(COF)C12
C6H2(N02)(CF3)C12
C6H(N02)2(COF)C12
C6H(N02)2(CF3)C12
C6H2(N02)(CH2F)C12
C6H(N02)2(CH2F)C12
C6H2(N02)(CHF2)C12
C6H(N02)2(CHF2)C12
C6H(N02) (COF)C13
C6H(N02)(CF3)C13
C6H(N02)2(COF)C13
C6H(N02)2(CF3)C13
C6H(N02)(CH2F)C13
C6(N02)2(CH2F)C13
C6H(N02) (CHF2)C13
C6H(N02) (CHF2)C13
f* U /MA \/^ll 1?
wCClA \W*'O /\*n*\E
C6H3.(N02)2CH2F
C6H2(N02)3CH2F
C6H4(N02)CHF2
Precursor
21
22
23
24
24
25
25
26
27
28
29
30
30
31
31
32
33
34
35
36
37
38'
39
Reaction (c)
Number
7
8
8
9
10
9
10
7
7
8
8
9
10
9
10
7
7
8
8
7
7
7
8
Likelihood of Being
. Present in ( .
Step^ ' Final Product1" '
4
4
4
4
4
4
4
4
4
4
4
4
4
4
4
4
4
4
4
4
4
4
4
0
0
0
0
•H-
0
+
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
382
-------
TABLE B-47. (Continued)•
No.
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
88
89
90
91
92
93
94
Contaminant^8' Precursor*1*'
C6H3(N02)2CHF2
C6H4(N02)COF
C6H4(N02)CF3
C6H3(N02)2COF
C6H3(N02)2CF3
PazNH
Pr2NH'HCl
C6H3(N02)(CONPr2)Cl
C6H3(N02)(COF)NPr2
C6H3(N02) (CONPr2)NPr2
C6H3(N02)(CF3)NPr2
C6H2(N02)2(CONPr2)Cl
C6H2(N02)2(COOH)NPr2
CfiH2 (N02) 2 (CONPr2)NPr2
C6H2(N02)2(CF3)NPr2
C6H3 (N02) (CH2F)NPr2
C6H2(N02)2(CH2F)NPr2
C6H3(N02)(CHF2)NPr2
C6H2(N02)2(CHF2)NPr2
C6H2(N02)(CONPr2)Cl2
C6H2(N02) (COF) (NPr2)Cl
C6H2(N02)(COF)(NPr2)2
C6H2(N02) (CONPr2) (NPr2)2
C6H4(N02)(CF3)(NPr2)Cl
40
41
41
42
42
SM
76
43
43
43
44
45
19
45
46
47
48
49
50
51
51
51
51
52
Reaction*0*
Number Step* '
8
9
10
9
10
-
14
13
11
11&13
11
13
11
11&13
11
11
11
11
11
13
11
11
116.13
11
4
4
4
4
4
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
Likelihood of Being
Present in . .
Final Product* ;
0
0
0
0
0
0
+
0
0
0
•H-
0
•*•
+
Triflutalin
0
0
0
0
0
0
0
0
+
383
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TABLE B-47. (Continued)
No.
95
96
97
98
99
100
101
102
103
104
105
106
107
108
109
110
111
112
113
114
115
116
(a)
Contaminant
C6H4(N02)(CF3)(NPr2)2
C6H(N02)2(CONPr2)Cl2
C6H(N02)2(CONPr2)(NPr2)Cl
C6H(N02)2(CONPr2) (NPr2)2
C6H(N02)2(COF) (NPr2)Cl
C6H(N02)2(CF3) (NPr2)Cl
C6H(N02)2(CF3)(NPr2)2
C6H2(N02) (CH2F) (NPr2)2Cl
C6H2(N02)(CH2F)(NPr2)2
RU /MA \ /f*tl H\ /MT>r* NP1
x ft ^NUM J r\ \L*MA" ) \WJrroyvJL
C6H(N02)2(CH2F)(NPr2)2
C6H2(N02) (CHF2) (NPr2)Cl
C6H2(N02)(CHF2)(NPr2)2
C6H(N02)2(CHF2) (NPr2)Cl
C6H(N02)2(CHF2)(NPr2)2
C6H(N02) (CONPr2)Cl3
C6H(N02) (COF) (NPr2)Cl2
C6H4 (N02) (COF) (NPr2)2Cl
C6H4(N02)(COF)(NPr2)3
C6H4(N02) (CONPr2) (NPr2)3
C6H(N02)(CF3)(NPr2)Cl2
C6H4(N02) (CF3) (NPr2)2Cl
Precursor
52
53
53
53
53
54
54
55
55
56
56
57
57
58
58
59
59
59
59
. 59
60
60
Reaction *C;
Number
11
13
11&13
11&13
11
11
11
11
11
11
11
11
11
11
11
13
11
11
11
11&13
11
11
Step
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
Likelihood of Being
Present in . .
Final Product16'
+
0
0
0
0
0
+
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
384
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TABLE B-47. (Continued)
No.
117
118
119
120
121
122
123
124
125
126
127
128
129
130
131
132
133
134
135
136
137
138
Contaminant
C6H4(N02)(CF3)(NPr2)3
C6H(N02)2(CONPr2)Cl3
C6H(N02)2(COF)(NPr2)Cl2
C6H(N02)2(COF) (NPr2)2Cl
C6H(N02)2(COF)(NPr2)3
C,H(NO,),(CONPr,) (NPr,),
O * Z £ £ j
C6H(N02)2(CF3) (NPr2)Cl2
C6H(N02)(CF3)(NPr2)2Cl
C6H4(N02)(CF3)(NPr2)3
C6H(N02) (CH2F) (NPr2)Cl2
C6H(N02) (CH2F) (NPr2)2Cl
C6H(N02)(CH2F)(NPr2)3
C6(N02)2(CH2F)(NPr2)Cl2
C6 (N02) 2 (CH2F) (NPr2) 2Cl
C6(N02)2(CH2F)(NPr2)3
C6H(N02) (CHF2) (NPr2)Cl2
C6H(NQ2) (CHF2) (NPr2)2Cl
C6H(N02)(CHF2)(NPr2)3
C6(N02)2(CHF2) (NPr2)Cl2
C6(N02)2(CHF2) (NPr2)2Cl
C6(N02)2(CHF2)(NPr2)3
C6H4(N02)(CONPr2)
Precursor '
60
61
61
61
61
61
62
62
62
63
63
63
64
64
64
65
65
65
66
66
66
72
Reaction (c)
Number
11
13
11
11
11
116.13
11
11
11
11
11
11
11
11
11
11
11
11
11
11
11
13
Step
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
Likelihood of Being
Present in ( .
Final Product*6'
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
385
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TABLE B-47. (Continued)
No.
139
140
141
142
143
144
(a)
Contaminant
C6H3(N02)2(CONPr2)
C6K2(N02)2(CF3)OH
C6H2(N02)2(CF3)OC2H5
C6H5CH2NPr2
C6H2(N02)2(CF3)NHPr
C6H2(NO.,)2(CF3)NH2
CF,
Precursor
74
46
46
5
85
143
(c
React ion v
Number
13
15
16
12
17
18
Step
5
3,5
3
5
5
5
Likelihood of Being
Present in .
Final Product^
0
•H-
+
0
+
+
145
146
85
145
19
20
(a) There are a number of different positional isomers possible for many of the contaminants.
(b) Precursor refers to the contaminant numbered in this table SM~starting material.
(c) to* Tabl* «-4|» ^
(d) TW »t«p (Figure B-28) during which the contaminant might be forned.
(e) 0 = likely to be present below 1 ppm.
+ •* likely to be present above 1 ppm but below 100 ppin.
-H- " likely to be present at levels above 100 ppm.
386
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TECHNICAL REPORT DATA
(Please read Instructions on the reverse before completing)
1. REPORT NO.
EPA-600/1-78-031
3. RECIPIENT'S ACCESSION-NO.
I. TITLE AND SUBTITLE
Identification of Toxic Impurities in Technical Grades
of Pesticides Designated as Substitute Chemicals
5. REPORT DATE
1Q7R
6.
ORMING ORGANIZATION C'ODE
7. AUTHOR(S)
J.S. Warner, A.E. Bearse, R.E. Wyant, and P.A. Clarke
8. PERFORMING ORGANIZATION REPORT NO.
9. PERFORMING ORGANIZATION NAME AND ADDRESS
Battelle Columbus Laboratories
505 King Avenue
Columbus, Ohio 43201
10. PROGRAM ELEMENT NO.
1EA615
11. CONTRACT/GRANT NO.
68-02-1705
12. SPONSORING AGENCY NAME AND ADDRESS
Health Effects Research Laboratory
Office of Research and Development
U.S. Environmental Protection Agency
Research Triangle Park, N.C. 27711
13. TYPE OF REPORT AND PERIOD COVERED
RTP,NC
14. SPONSORING AGENCY CODE
EPA 600/11
15. SUPPLEMENTARY NOTES
16. ABSTRACT
Two different approaches were used to identify potentially harmful impurities
present in technical grade pesticides. One approach was a theoretical approach
that involved a literature search, study the manufacturing processes, identifying
the main reactions and the numerous side reactions that may occur, listing the
potential impurities that may result, and estimating the likelihood of the occurrence
of such impurities at ug/g or lower levels in the final product. The second
approach was experimental and involved the use of combined gas chromatography-mass
spectrometry (GC-MS) to identify and quantify the major impurities actually present
in technical-grade materials.
In addition to the above two tasks the program also included maintaining,and
assaying a repository of selected technical-grade pesticides.
7.
KEY WORDS AND DOCUMENT ANALYSIS
DESCRIPTORS
b.IDENTIFIERS/OPEN ENDED TERMS
COSATi Field/Group
pesticides
chemical analysis
07 C
21. NO. OF PAGES
397
3. DISTRIBUTION STATEMENT
RELEASE TO PUBLIC
19. SECURITY CLASS (This Report)
UNCLASSIFIED
20. SECURITY CLASS (This page)
UNCLASSIFIED
22. PRICE
EPA Form 2220-1 (9-73)
387
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