EPA-600/2-77-023h
January 1977
Environmental Protection Technology Series
INDUSTRIAL PROCESS PROFILES FOR
ENVIRONMENTAL USE: Chapter 8.
Pesticides Industry
Industrial Environmental 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. Environmental
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 consciously
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 PROTECTION
TECHNOLOGY series. This series describes research performed to develop and
demonstrate instrumentation, equipment, and methodology to repair or prevent
environmental degradation from point and non-point sources of pollution. This
work provides the new or improved technology required for the control and
treatment of pollution sources to meet environmental quality standards.
EPA REVIEW NOTICE
This report has been reviewed by the U.S. Environmental
Protection Agency, and approved for publication. Approval
does not signify that the contents necessarily reflect the
views and policy of the Agency, nor does mention of trade
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recommendation for use.
This document is available to the public through the National Technical Informa-
tion Service, Springfield, Virginia 22161
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EPA-600/2-77 -023h
January 1977
IN D U S TRIA L PRO C E SSP R 0 F I L E S
FOR ENVIRONMENTAL USE:
CHAPTER 8.
PESTICIDES INDUSTRY
by
F.L Honea (Midwest Research Institute)
Terry Pars ons, Editor
Radian Corporation
P. O. Box 9948
Austin, Texas 78766
Contract No. 68-02-1319, Task 34
ROAP No. 21AFH-025
Program Element No. lAB015
EPA Project Officer: LA. Jefcoat
Industrial Environmental Research Laboratory
Office of Energy, Minerals, and Industry
Research Triangle Park, NC 27711
Prepared for
U. S. E NVffiONlV1E NT AL PROTE CTION AGENCY
Office of Research and Development
Washington, DC 20460
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TABLE OF CONTENTS
CHAPTER 8
INDUS TRY DES CRIPTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Raw Materials. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Produc ts. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Companie s. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Environmen tal Impact.................................................
Bibliography. . . . . . . . . . . . . . . . . . .. . . . . . . .. . . . . . . . . . . . . . . . . .. . . .. .. . . . . .
INDUS TRY ANAL YS IS. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Simple and Aromatic Chlorinated Hydrocarbon Pesticides. ..... ...... ...
Process No. l.
Process No.2.
Process No.3.
Process No.4.
Process No.5.
Process No.6.
Dichlorobenzene Chlorination Process... ...... ......
DDT Process.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Pentachlorophenol (PCP) Process..... ............ ...
2. 4-D Process.....................................
2, 4-DB Process....................................
Toxaphene Process. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Diene-Based Chlorinated Pes ticides. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Process
Process
Process
Process
Process
Process
Process
No.7.
No.8.
No.9.
No. 10.
No. ll.
No. 12.
No. 13.
Hexachlorocyc1opentadiene Process... ... ...... ......
Hexach1orocyclopentadiene Process (alternate) ... ...
Diene Process. Aldrin..............................
Isodrin Process..... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Endrin Process... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Dieldrin Process. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Chlordane Process.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Organophosphate Pes ticides. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Process No. 14. H-Replacement Organophosphate Process, Malathion...
Process No. 15. Na-Replacement Organophosphate Process, Disulfoton.
Process No. 16. Cl-Rep1acement Organophosphate Process,
Methyl Parathion.................................................
Process No. 17. CI-Replacement Organophosphate Process, Parathion..
Process No. 18. CI-Rep1acement Organophosphate Process, Diazinon...
Carbamate Pesticides......... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Process No.
Process No.
Process No.
19. Amine Addition Process, CarbaryL..................
20. Carbamate Process, Carbofuran......................
21. Carbamic Acid Salt Replacement Process, ~aneb... ...
Triazine Pes ticides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Process No. 22. Atrazine Process. ...... ... ..... ........ .... .......
Anilide Pes ti cides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Process No. 23. An; 1; ne Process, Alachlor..........................
iii
Page
1
2
2
3
6
10
11
13
19
21
23
24
27
28
29
33
34
35
36
37
38
39
41
50
51
53
54
56
57
63
65
66
67
71
72
75
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TABLE OF CONTENTS (Continued)
CHAPTER 8
Urea and Uracil Pesticides...... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Process No. 24.
Process No. 25.
Bromacil Process..................................
Amine Addition Process, Diuron....................
Nitrated Hydrocarbon Pesticides.. ..... ...... ...... .......... .........
Process No. 26.
Process No. 27.
Trifluralin Process.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Benefin Process................ . . . . . . . . . . . . . . . . . . .
Other Nitrogenous Pes ticides. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Process No. 28.
Process No. 29.
Process No. 30.
Imide Pesticide Process, Cap tan. . . . . . . . . . . .. . . . . . .
Imide Pesticide Process, Folpet...................
Maleic Hydrazide Process............. .... .........
Organoarsenic and Organometallic Pesticides....... ...... ...... .......
Process No. 31.
Process No. 32.
Process No. 33.
DSMA Process. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 101
MSMA Process...................................... 103
Cacodylic Acid Process.. .................... ... ...104
Page
76
81
82
83
87
88
89
93
95
96
97
Microbial and Natural-Occurring Pesticides........................... 105
Process No. 34. Bacillus thuringienses Process. .... ...... ...... ...108
Process No. 35. Pyrethrin Process............. ...... ...... ........109
Other Pes ticides. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 110
Process No. 36.
Process No. 37.
Methyl Bromide Process........ ..... ...... .........113
Endothall Process..............>................... 114
Appendix A - Lists of Process Input Materials for the
Pesticides Industry[[[ 115
Appendix B - U.S. Tariff Commission List of
Pesticides.. ........ ... .....129
Appendix C - Stanford Research Institute List of Pesticides
and Producers.......... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 133
Appendix D - Midwest Research Institute Summary of Pesticides
Not Listed by the U.S. Tariff Commission.. ................ ...... ... ...
Appendix E - Midwest Research Institute Estimate Pesticide
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Figure
10
11
12
LIST OF FIGURES
CHAPTER 8
1
Synthesis of Some Chlorinated Hydrocarbons and
Related Pesticides. . . . . . . . . . . . . . . . . . . .
Page
15
16
17
Ie
31
32
45
4E
47
48
49
60
13 Flow Sheet for Carbamate Pesticide Processes . . . . .
14 Flow Sheet for Dithiocarbamic Acid Salt Pesticide
Processes. . . . . . . . . . . . . . . . . . . . . 62
2
Flow Sheet for Simple Chlorinated Hydrocarbon Pesticides
and Intermediate Chemicals. . . . . . . . . . . . . . . .
3
Flow Sheet for DDT and Some Aromatic Chlorinated
Hydrocarbon Pesticides. . . . . . . . . . . .
. . . . . .
4
Flow Sheet for Aromatic Chlorinated Hydrocarbon
Pesticides. . . . . . . . . . . .
. . . 0 . .
5
Synthesis of the Diene Group of Chlorinated Insecticides--
From Hexachlorocyclopentadiene . . . . . . . . . . . . . .
6
Flow Sheet for Diene-Based Pesticides Processes.
7
Chemical Reactions for Organophosphate Pesticides from
Phosphorus Pentasulfide (P2S5) . . . . . . . . . . .
8
Chemical Reactions for Organophosphate Pesticides from
Phosphorus Trichlorosulfide. . . . . . . . . . . . .
9
Chemical Reactions for Organophosphate Pesticides from
Other Phosphorous Compounds. . . . . . . . . . . . .
Flow Sheet for Organophosphate Pesticide Processes
. 0 0 CI .
Flow Sheet for Other Organophosphate Pesticide Processes. .
Typical Chemical Reactions to Produce Carbamate
Pesticides. . . . . . . . . . . . . e 8 . e 8
. . . .. e .
v
61
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Figure
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
LIST OF FIGURES (Concluded)
CHAPTER 8
Synthesis of Triazine Pesticides. . . . . .
. . . . . . . .
Flow Sheet for Triazine Pesticide Processes.
........
Chemical Reactions for Production of Anilide Pesticides. .
Flow Sheet for Anilide Pesticide Processes. . . . . .
Chemical Reactions to Form Urea and Uracil Pesticides
Flow Sheet for Urea and Uracil Pesticide Processes. .
Chemical Reactions to Produce the Nitrated Hydrocarbon
Pesticides. . . . . . . . . . . . . . . . . . . . . . . .
Flow Sheet for Nitrated Hydrocarbon Pesticide Processes. .
Chemical Reactions and Structures for Imides, Amides
and Other Nitrogenous Pesticides. . . . . . . . . .
Flow Sheet for Imides and Other Nitrogenous Pesticide
Proe e sse s . .. . . . . . . . . . . . . . . . .
Flow Sheet for Other Nitrogenous Pesticide Processes.
Chemical Reactions to Produce Organoarsenic and
Organometallic Pesticides. . . . . . . . . .
. . . . . .
Flow Sheet for Organoarsenic and Organometallic Pesticide
Processes. . . . . . . . . . . . . . . . . .
. . . . . .
Flow Sheet for Microbial and Natural-Occurring Pesticide
Pr 0 C e sse s . . . . . . . . . . . . . . . . . . . . . . . .
Other Pesticides Chemical Reactions and Structures.
. . . .
Flow Sheet for Other Pesticide Processes. . . . . .
. . . .
vi
Page
65
70
73
74
77
79
84
85
90
91
92
98
99
107
110
111
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Table
1
2
3
4
5
6
7
A-l
A-2
A-3
A-4
A-5
A-6
A-7
A-B
A-9
A-10
A-ll
D-l
LIST OF TABLES
CHAPTER 8
Selected Pesticide Plant Locations and Capacities in 1972. .
Organic Chemicals Found in Pesticide Plant Effluents.
Waste Characteristics of Chlorinated Herbicide Wastes.
The Chemical Structure of Acyclic Organophosphate
Pesticides. . . . . . . . . . . . . . . . . 0
. . .. CI . .
The Chemical Structure of Cyclic Organophosphate
Pesticides. . . . . . . . . . . . . . . c .
o . . .
Structure of Carbamate and Thiocarbamate Pesticides.
. . . .
Urea Pesticides Structure.
....0
810.."$.
o e co . 0
Chlorinated Hydrocarbon Pesticides
0000.
o 0 Q .
.. " . .
Diene-Based Pesticides. . .
. CI " 0 C .
00810(>1:10
Organophosphate Pesticides
o .. CI CI ..
0....
.. . .. ..
Carbamate Pesticides
. .. . .
0..08
.. .. CI . II
Triazine Pesticides. . .
. . .. .
.....8
8.......
Anilide Pesticides.
. .. . 0
.......
Urea and Uracil Pesticides.
.. .. .. .
Nitrated Hydrocarbon Pesticides.
..G..
. .. .. .
.. . .. . ..
Other Nitrogenous Pesticides. .
. . .0..
. . . . . .
Arsenical and Metallic Pesticides.
. . 8 .
. .. .. . .. 0
Other Pesticides. . . .
.. . . .
.. . " . ..
. . .. .. .
. . . ..
Pesticides Not Listed in "Pesticides and Related
Products" Section of Synthetic Organic Chemicals
United States Production and Sales (Annual) by
United States Tariff Commission. . . . . . . . .
. . .. . .
vii
Page
4
7
26
42
44
58
78
116
117
118
120
121
122
123
124
125
126
127
218
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PESTICIDES INDUSTRY
INDUSTRY DESCRIPTION
This industry produces the organic chemicals known as pesticides, which
are used to control agricultural pests such as insects, fungus, plants
and rodents, to disinfect and condition soil, and as plant hormones. This
industry includes only the bulk producers and does not include other pro-
ducers of preparations made from the chemicals. The inorganic chemicals,
petroleum products and creosote used as pesticides are specifically excluded
from this study. Such materials represent a minor use of the product chemi-
calor are products or by-products of processes addressed in other industries.
Many products of this industry are produced by single producers. A nar-
row product line is either the reflection of the success of a particular
line of research and the consequent proprietary position developed by the
producer or an indication of similar processes utilizing the same produc-
tion equipment, The rapid growth of herbicides and insecticides has been
tempered by the increasing attention to long-term residual environmental
effects. On the other hand, the growing worldwide need for food will con-
tinue to generate the pressure for fast-acting, selective and specific
pesticides.
Over 550 pesticides have been identified, with about 200 pesticides in
current production and use. Many different processes and input materials
are used for these various pesticides. As a result, to present a clearer
picture of the process relationships in the pesticide industry, the pesti-
cides have been separated into 12 industrial segments with similar chemical
structures and reactions. The industry segments are:
a.
Simple and aromatic chlorinated hydrocarbons;
Diene-based;
Organophosphates;
Carbamates and thiocarbamates;
Triazines;
Anilides;
b.
c.
d.
e.
f.
1
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i.
Ureas and uraci1s;
Nitrated hydrocarbons;
Other nitrogenous;
Organoarsenicals and organometa11ics;
Microbial or natural derivatives; and
Others.
g.
h.
j.
k.
1.
These segments are described in more detail in a later section of this
report. The section on pesticide industry segments includes a descrip-
tion of each pesticide group with typical uses, chemical structures and
reactions and input materials. Representative flow sheets are included
to indicate the interrelationship and similarities of the pesticide pro-
cesses in each group.
The production volume for the pesticides industry has been reported at
1,258 million pounds in 1972 by the u.s. Tariff Commission. By-products
from other industries (e.g., creosote) accounted for over 1 billion addi-
tional pounds. For proprietary reasons, detailed production information
on pesticides with only one or two producers is not reported by the Tariff
Commission. Also, disparities have been noted between reportea production
volumes and sales. From industrial contacts and the Tariff COtrnnission in-
formation, Dr. Edward W. Lawless at the Midwest Research Institute has
conducted an in-house review of the pesticide production. This MRI esti-
mate of production for 1972 is presented in Appendix E.
Major pesticide production plants with capacities over 5 million pounds
are located in 25 states. Many plants are found near the coasts in close
proximity to refineries for supply of petroleum and ch1or-a1ka1i feed-
stocks. The size of the pesticide plants varies from less than 50,000
1b/year up to 200 million pounds per year.
According to information reported by Stanford Research Institute (SRI),
the projected average growth through 1980 for pesticide production is 6
to 8%/year, which is slightly greater than expected growth in consumption.
The difference will be exported to meet the projected 10%/year average
growth in pesticide demand worldwide. The trend will be to develop highly
selective pesticide formulations from commercially available chemicals.
The prohibitive cost of determining the environmental impact of any new
pesticide is likely to deter development and introduction of new chemi-
cals as broad-based pesticides. The replacement of chemical insecticides
by hormones and pheromones will be gradual. Much depends on future de-
velopment of effective methods of application and on farmer education.
2
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Information on the energy requirements for the pesticide industry is
not generally available since many products are proprietary- The feed-
stock raw materials such as chlorine and sodium hydroxide may require
large amounts of energy if electrolysis of brine solution is used. How-
ever, most of these feedstocks are actually products of the chlor-alkali,
petroleum and chemical industries. The final pesticide reactions them-
selves require relatively low amounts of energy for heating and maintain-
ing reaction temperatures, for some reflux and stripping operations and
for pumping of fluids.
Raw Materials
A list of the raw materials required to produce each pesticide is in-
cluded in Appendix A. This list is divided into the industrial segments.
The raw materials include many petroleum-based hydrocarbon chemicals from
the petroleum and chemical industry and some chlorine and sodium hydrox-
ide from salt electrolysis or from the chlor-alkali industry. Large
amounts of sulfuric and nitric acids are also used from the inorganic
chemical industry. The gases including chlorine, phosgene and ammonia
used in the production of some pesticides can be extremely toxic if re-
leased to the atmosphere. The heavy metal, arsenic, cyanide, and phos-
phate raw materials can also be a health hazard in water and air. The
bases and acids are potentially corrosive and can present a health hazard.
Products
Over 200 pesticides are in current production and use in the United
States. These pesticides are used as insecticides, herbicides, fungi-
cides, fumigants, rodenticides, and for other purposes. Some of the
pesticide products are also used as input materials for other pesticide
processes.
Products of this industry which have been identified by the U.S. Tariff
Commission are listed in Appendix B. These products are classified in
SIC 28694. Company listings for these products and other pesticides
have been compiled by the Stanford Research Institute from their Direc-
tory of Chemical Producers - USA. The SRI compilation is included as
Appendix C. Some pesticides which are not included by the U.S. Tariff
Commission are listed in Appendix D.
Companies
Over 25 companies are major producers of pesticides with production ca-
pacities above 5 million pounds. The largest plants for some major pro-
ducers are listed in Table 1. Most of the producers of bulk insecticides
3
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Table 1.
SELECTED PESTICIDE PLANT LOCATIONS AND CAPACITIES IN 1972
Company
Ciba-Geigy Corporation
Tennco Chemicals, Inc.
Monsanto Chemicals
~
Dow Chemical Company
Hercules, Inc.
Union Carbide Cor-
poration
E. 1. du Pont de
Nemours and Company
Pesticide
Atrazine
Diazinon
Toxaphene
Alachlor
Maneb (dithio-
carbamates)
Pentachlorophenol
Methyl parathion
and parathion
2,4-D
Pentachlorophenol
Dichlorobenzene
Methyl bromide
Toxaphene
Carbaryl
Uracils (Bromacil)
Ureas (Diuron)
Plant location
Estimated plant capacity
(million pounds)
McIntosh, Alabama
St. Gabriel, Louisiana
200
15
Fords, New Jersey
125
Muscatine, Iowa
30
15 -20
Sauget, Illinois
Anniston, Alabama
26
50
Midland, Michigan
45-50
18
16
15
Brunswick, Georgia
50-75
Institute, West Virginia
65
LaPorte, Texas
20
30
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Table 1 (Concluded)
Company
Eli Lilly and Company
Ve Is ico 1
American Cyanamid
Stauffer Chemical
Company
\Jt
Ansul Company
Diamond Shamrock
Chemica I Company
Ca lh io Chemica 1
Rohm and Haas Company
Shell Chemical
Company
Pesticide
Trifluralin
Chlordane
Organophosphates
Malathion
Parathion and
methyl parathion
MSMA
MSMA
Captan
Dithiocarbamates
Aldrin
Plant location
Estimated plant capacity
(million pounds)
Lafayette, Indiana
35
Marshall, Illinois
Bayport, Texas
30
10
Warners, New Jersey
35
Mount Pleasant, Tennessee
30
Marinette, Wisconsin
25
Green Bayou, Texas
20
Perry, Ohio
25
Philadelphia, Pennsylvania
20-25
Denver, Colorado
20
-------
are chemical companies with a
However, the pesticide plants
other chemical processes, and
related pesticide products.
few petroleum and
or facilities are
most equipment is
farm chemical companies.
usually separate from
dedicated to specific or
The plants are located throughout the United States in about 25 states.
Many pesticide producers are located near refineries and seacoasts to
obtain petroleum and chlor-alkali feedstocks.
Environmental Impact
The pesticide industry produces many products which are toxic to humans
and many more which are toxic or harmful to animals, fowl, fish, bene-
ficial insects, and plants. These effects can be minimized by use of
the least harmful, effective pesticide mixture with control of pesticide
distribution, proper handling procedures and application. Even with
these precautions, poisonous and carcinogenic pesticide residues are
found in runoff water from land used for agricultural purposes. Some
of these pesticides and pesticide residues have also been identified in
the waste streams coming from pesticide production plants. The pesticide
residues in plant waste streams and in agricultural runoff waters are
thought by some authorities to constitute a serious public health hazard.
It should be mentioned that there is the possibility that the chlorinated
hydrocarbons found in drinking water are formed during chlorination water
treatment. However, with the presently available information, it would
appear that the organic substances occurring in drinking water are for the
large part of industrial origin. Although data on the composition of
liquid waste streams from pesticide manufacturing processes are not avail-
able in the open literature, evidence exists that various organic materials
are present in liquid wastes. Some organic chemicals found in pesticide
plant effluents in an ongoing EPA monitoring study on carcinogens in water
supplies are listed in Table 2.
Some of the feedstock chemicals and intermediate chemicals used in pes-
ticide production also have hazardous toxic or corrosive properties. The
gases including chlorine, phosgene and ammonia represent potential toxic
hazards. Heavy metals, arsenic, cyanide, phosphate and partially chlori-
nated hydrocarbons also represent potential toxic hazards. In addition,
the acids and bases used represent potential hazards to health and safety.
6
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Table 2. ORGANIC CKEMICALS FOUND IN
PESTICIDE PLANT EFFLUENT~I
Acenaphthene
Aldrin
Chlordane
Chlordene
m-Cresol
.E.- Cymene
Dieldrin
Dimethyl naphthalene isomer
Diphenyl ether
Endrin
Ethyl naphthalene ether
Tetramethylbenzene isomer
Trichlorocyclopentene isomer
Pentachlorocyclopentadiene isomers
Pentachloronorbonadiene isomer
Pentachloronorbornene isomer
Pentachloronorbornadiene epoxide isomer
Octachlorocyclopentene
Methyl naphthalene isomers
Naphthalene
Hydroxybiphenyl isomer
Isodrin
Jasmone
Heptachlor
Heptachloronorbornene isomers
Hexachlor epoxide
Hexachlorobutadiene
Hexachlorocyclopentadiene
Hexachloronorbonadiene isomers
Hexadieneal
!!I
From Ref. 8 in the bibliography.
7
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The pesticide industry is aware of the toxic nature of some of its prod-
ucts and has taken steps to protect the industry workers and to control
leakage or venting of toxic materials. Since many pesticide processes
are proprietary, very little information is available on the potential
toxic ingredients included in the air, water and solid wastes from these
processes. Accurate information on production amounts and raw materials
is even difficult to obtain for many pesticides. This lack of informa-
tion prevents a full evaluation of the potential health effects from
pesticide manufacturing wastes and of the environmental control methods
in use by the pesticide industry.
The characterization of waste streams and of treatment or disposal methods
in the process descriptions may appear to be overly simplistic. This
appearance is a direct result of the lack of meaningful process data
characteristic of this industry. In most cases the waste streams can be
expected to contain unreacted raw materials, reaction byproducts or pesti-
cide products, but difinitive information has never been published. An
indication in the process description that the waste material is fltreatedfl
and/or fldischarged", unaccompanied by more specific information, reflects
the almost total lack of treatment data.
Available information indicates that the equipment used to produce pest-
icides is usually isolated from other company activities and is dedicated
to one pesticide or similar pesticides. The gaseous emissions are often
controlled by condensation recovery, scrubbing and flares. Liquid ef-
fluents from the processes and from the gas scrubbing systems represent
the biggest pollution source. These liquid effluents may undergo many
separation treatments including stripping, decanting, filtration, set-
tling, and adsorption. Often, the most toxic waste streams have been in-
jected in deep wells, dumped at sea or dewatered and buried in landfill
sites.
------- ~--
A newer technique has been the incineration at sea on a special incinerator
ship (by Shell Chemical under EPA supervision). Many pesticide residues,
cancelled pesticides and waste products may also be incinerated success-
fully. Recently a pilot level study was conducted to determine incinerator
operating condition necessary for safe disposal of pesticides. Nine pesti-
cides in 15 liquid and solid formulation were investigated. The pesticide
studied were DDT, aldrin, picloram, malathion, toxaphene, atrazine, captan,
zineb and mirex. The formulated pesticide was injected into the primary
combustion chamber of the incinerator. Destruction efficiencies of greater
than 99.99 per cent were achieved for all pesticides tested except mirex
over a range of combustion chamber temperature/retention time combinations.
8
-------
Emissions containing potentially hazardous components may occur not only
in the form of process waste streams but also from housekeeping and spill
cleanup operations, during packaging operations, and in effluent from
laundering of worker protective clothing. Estimates of the quantity and
composition of waste produced annually during pesticide manufacture have
been published9 and summarized.10 It is reported that 5.4 x 103 metric
tons (5.9 x 103 short tons) of accumulated surplus pesticides are currently
stored in government facilities.9
The Office of Solid Waste Management.Programs, EPA, is currently investi-
gating potentially hazardous effluents from this industry destined for
land disposal. The results will be available soon in a series of studies
entitled Assessment of Industrial Hazardous Waste Practices. Organic
Chemicals, Pesticides, and Explosives.
9
-------
Bibliography
(10)
(IV
(1)
Lawless, E. W., R. von R~mker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-00-72-04, June 1972. NTIS Publication.
(2)
von Rumker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-31l, Final Report, 15 March 1974.
(3)
Lawless, E. W., T. L. Ferguson, and A. F. Meiners, Guidelines for
Disposal of Small Quantities of Unused Pesticides, Midwest Research
Institute for U.S. EPA, Contract No. 68-01-0098, NERC-Cincinnati,
31 August 1974.
(4)
Sittig, M., Agricultural Chemicals Manufacture, Noyes Ddta Corp-
oration, Chemical Process Review No. 52 (1971).
(5)
Sittig, M., Pesticide Production Processes 1967, Noyes Development
Corporation, Park Ridge, New Jersey (1967).
(6)
Ferguson, T. L., F. J. Bergman, G. R. Cooper, R. T. Li, and F. I.
Honea, Pilot Scale Incineration of Pesticides, Vol. I, Midwest
Research Institute for U.S. EPA, Contract No. 68-03-0286, NERC-
Cincinnati, May 1975.
(7)
Ferguson, T. L., F. J. Bergman, G. R. Cooper, R. T. Li, and F. I. Honea,
Determination of Incinerator Operating Conditions Necessary for Safe
Disposal of Pesticides, Midwest Research Institute for U.S. EPA,
Contract No. 68-03-0286, EPA-600/2-75-041, NERC, Cincinnati, December 1975.
(8)
Martin, H., Pesticide Manual, British Crop Protection.Counci1,
Second Edition (1972).
(8)
Suspect Carcinogens in Water Supplies, Interim Report, U.S. EPA,
Office of Research and Development, April 1975.
Ottinger, R. S., et al., Recommended Methods of Reduction, Neutrali-
zation, Recovery or Disposal of Hazardous Waste, Vol. 14, Summary
of Waste Origins, Forms, and Quantities, Contract No. 68-03-0089,
EPA 670/2-73-053-N, Redondo Beach, Ca., TRW Systems Group, 1973.
Battelle Memorial Inst., Pacific Northwest Labs., Program for the
Management of Hazardous Wastes, Final Report, 2 Vols., Contract
No. 68-01-0762, PB-233-630, PB-233-63l, Richland, Washington, 1973.
10
-------
INDUSTRY ANALYSIS
The pesticide industry has produced over 550 diffferent pesticides. and
about 200 of these pesticides are in current production. Because of the
variety of chemical compounds in production as pesticides, many processes
are used. For many pesticides with similar chemical structure, the pro-
duction processes are similar. For other pesticides derived from a common
raw material, the processes are also similar. Based on these similar com-
pounds or those with a common input raw material, the pesticide industry
has been divided into 12 industrial segments.
Data for the industry analysis are presented in 12 sections, one for
each segment of the industry. The order of presentation is:
l.
2.
3.
4.
5.
6.
7.
8.
9.
10.
1l.
12.
Simple and aromatic chlorinated pesticides;
Diene-based chlorinated pesticides;
Organophosphate pesticides;
Carbamate pesticides;
Triazine pesticides;
Anilide pesticides;
Urea and uracil pesticides;
Nitrated'hydrocarbon pesticides;
Other nitrogenous pesticides;
Organoarsenic and organometallic pesticides;
Microbial and natural-occurring pesticides; and
Other pesticides.
Each of the above 12 segments is further broken into component processes.
The chemical reaction trees and process flow sheets for individual industry
segments are shown in Figures 1 through 31, with process interrelationships
schematically presented on the flow sheets. Each chemical reaction tree
and process flow sheet immediately follows its respective industry segment
description. Processes within a particular segment are described sequentially
in the section immediately following the figure on which they are shown.
Many of the production operations in the industry are proprietary, and descrip-
tive process data are either quite limited or not available. Because of this
lack of detailed information chemical trees and process flow sheets are some-
what generalized. Separate process descriptions are included to characterize
those processes for which even limited data have been found. The process
descriptions presented in this study are numbered consecutively and are
represented by identically numbered rectangles shown on the flow sheets.
Processes for which no information was found are represented by unnumbered
rectangles on the flow sheets. In addition, such processes are listed at
the end of each segment description.
11
-------
Within each process description available data have been presented on operating
variables and waste streams associated with that process. Process rectangles
on the flow sheets are flagged to indicate the presence of gaseous, liquid
and/or solid waste streams. For most pesticide processes, little or no infor-
mation is available on potential pollution problems, emissions, effluents,
solid wastes, applied control technology and energy usage. For some processes,
no information is available beyond potential input materials or example chemi-
cal reactions cited in patent applications.
Some pesticides can be produced by as many as eight different processes, none
specifically identified with a particular producer or plant. For some of the
more popular pesticides, such as atrazine, information originally supplied by
the producer to MRI for other pesticide studies has been incorporated herein.
For other pesticides, much more data is needed from the producers in order to
make a proper evaluation of the pollution potential for their respective pro-
cesses and for the industry as a whole.
12
-------
Simple and Aromatic Chlorinated Hydrocarbon Pesticides
A large family of
matic chlorinated
hydrocarbons with
about 90 pesticides is classified as simple and aro-
pesticides. These pesticides include acylic and cyclic
at least one chlorine atom.
The simple and aromatic chlorinated hydrocarbon pesticides can be sepa-
rated into three groups: (a) simple chlorinated hydrocarbons; (b) DDT-
family of chlorinated hydrocarbons; and (c) aromatic-chlorinated hydro-
carbons. The "phenoxie" pesticides have phenol as a base and are included
as aromatic chlorinated hydrocarbons. The simple chlorinated hydrocarbon
pesticides have no common configuration. DDT, DDD, methoxychlor and hexa-
chlorophene include two aromatic rings in a "di" configuration. The gen-
eral structure of the aromatic-chlorinated hydrocarbons is:
Rl
::@::
R4
where at least one R group is chlorine as summarized in the following
tabulation.
Aromatic pesticide
"Phenoxies"
2 ,4-D
2,4-DB
MCPA
MCPB
2,4,5-T
Silvex
Bromoxynil
PCP
2,4,5-Trichlorophenol
Others
PCNP
2,3,6-TBA
Chloramben
Dichlorobenzene
Hexachlorobenzene
Dicamba
Rl
- OCH2 COOH
-OCHZ CHZ COOH
-OCHZCOOH
- CHZ CHZ COOH
-OCHZ COOH
-OCH( CH3) COOH
-CN
-OH
-OH
-NOZ
-COOH
- COOH
-Cl
-Cl
- COOH
13
RZ
-Cl
-Cl
-CH3
-CH3
-Cl
-Cl
-H
-Cl
-Cl
-Cl
-Cl
-H
-H
-Cl
-OCH3
R3
-H
-H
-H
-H
-H
-H
-Br
-Cl
-H
-Cl
-H
-Cl
-H
-Cl
-Cl
R4
-Cl
-Cl
-Cl
-Cl
-Cl
-Cl
-OH
-Cl
-Cl
-Cl
-Cl
-H
-Cl
-Cl
-H
RS
-H
-H
-H
-H
-Cl
-Cl
-Br
-Cl
-Cl
-Cl
-H
-NH2
-H
-Cl
-H
R6
-H
-H
-H
-H
-H
-H
-H
-Cl
-H
-Cl
-Cl
-Cl
-H
-Cl
-Cl
-------
The "phenoxies" are more connnonly available in a salt form compared to
the acid form. 2,4-D is also sold in an ester form. Although bromoxynil
is a brominated aromatic hydrocarbon, it is still often classified as a
"phenoxie" and is included here.
The annual production in 1972 of the chlorinated hydrocarbon pesticides
included in this industry segment is estimated at over 380 million pounds
(about 30% of all pesticides). Toxaphene, which is the most popular pest-
icide, accounts for 95 million pounds. DDT still accounts for 40 million
pounds as an insecticide, and methoxychlor accounts for 3 million. The
"phenoxies" are used as herbicides with 2,4-D amine salts at 22.7 million
pounds and acids and esters at 30 million pounds. Other "phenoxies" in-
clude 2,4,5-T at 7 million pounds, Silvex at 3 million pounds, and ~~PA
at 2 million pounds.
Herbicides include chloramben at 20 million pounds and TCA at 11.3 mil-
lion pounds. Fungicides include PCP at 49.7 million pounds and 2,4,5-
trichlorophenol at 18 million pounds. In addition, soil fumigants include
dichloropropene at 20 million pounds.
The use of the DDT family and toxaphene pesticides is expected to decrease
as substitutes are found.
Many of the chemical reactions for chlorinated hydrocarbon pesticides are
indicated in Figure 1. Figure 2 is the flow sheet for the simple chlori-
nated hydrocarbon pesticides. The flow sheets for the DDT family and
other chlorinated aromatic hydrocarbons are presented in Figures 3 and 4.
Data on several of the individual processes in this industry segment were
not available in the literature and detailed process descriptions could
not be prepared. These processes are:
Methoxychlor Process
DDD Process
Trichlorophenol Process
Dichlorophenol Process
MCPA Process
MCPB Process
Hexachlorophene Process
2,4,5-T Process
Silvex Process
Dicamba Process
Hexachlorobenzene Process
Benzene Hexachloride (BHC) Process
Dachtal Process
TBA Process
Chloramben Process
14
-------
METHOXYCHLOR .QQ! 2,4,5-Trichlorophenol
~CI~ ~CCI3~ rAtCI CIr(YoH CI 2,4-08
C"O~~\Q;OC" C'O~H\Q/' CO~(" &' C'~CI @'70OH
>Ox"'.., ~"""'o 'C::JA '-= C! \'OH"/ ;;70 CI
H "/T) @\7 O~
CI.-.C\:JLcH3 CCI3CHO ~ NoOH.. 0 C'l ~
~(CH3>2 ~ ~ OH OCHi=OOH
(67-69 % CI) CJyrc.y..O @CI NoOH .. @CI
CICH2COOH
CI
r(Y DICHlOROBENZENf CI CI
l8J Cl OH
CI egCI @CI 1.!,H
~ OCH2COOH
CO CO 9 C! 9 ~rgCI
ClegCI
~ CI
CI CI r~......1;o CI
CI HEXACHlOROBENZfNf '>C'
-------
Ch lori notion
Process
Pesticide !Dp-uts~/
Bicyclopentodiene
Mixed T erpenes
Ethylene
Acetone
Acetic Acid + CJ2
Acetic Acid + CI2
Propionic Acid
Benzene
Nitrobenzene
1, 3-di chloro-
2-proponol
Pesticides 2../
Bondone
Strobone
Ethylene Dichloride
Hexoch lorocetone
Chloroocetic Acid -- CD
TCA
Dolopon
1,4-dichlorobenzene
PCNB
Di ch loropropene
Intermediote ~p'uts ~
Toluene
Benzyl-ocetic Acid
Ethanol
Ethanol
Benzene
Benzene
o-cresol
* Intermediote Chemicols ~
Trichlorotoluene (C6H2CI3CH3)--0
Dichlorobenzyl Acetic Acid (C6H3CI2COOH)--@
CCI2HCHO--J4)
CCI3CHO--~
Chlorobenzene (C6HSCI)--@
Tetrochlorobenzene (C6H2CI4)-=--<2)
4-chlaro-o-cresol (C7H7CI 0 )--@
~/ These input chemicals are required to produce the pesticides
directly in line across the process
£/ These intermediate input chemicals are required to produce the
inline intermediate chemicals. The intermediate chemicals are
used in other pesticide processes as indicated in Figures 3 and 4.
Figure 2.
Flow sheet for simple chlorinated hydrocarbon pesticides
and intermediate chemicals
16
-------
8-
~
1 acetic
Acid
.
M.thoxychlar
Process
=:1 ODD p~,= I
DDT Process
2
Dichlorophenol
Process
. Chlorinated intermediate chemicals
{see Fi gure 2)
H20
~8
HCI
PC P Process
2,4-D Process
4
2.4-DB Process
5
MCPB Process
Flo~v Sheet for DDT and some aromatic chlorinated
hydrocarbon pesticides
17
Figure 3.
-------
NoOH +
Methanol
1. C02
2. Dimethyl Sulfate
Cotal)"'t
Hexach loro-
benzene
Proceu
uv
~
C6H4(COClh
U-
e-
Benzene
Hexoch loride
Prexess
HCI
~
('
~ TBA Process I
-8
* Chlorinated intermediate chemicals
(see Figure 2)
Flow sheet for aromatic chlorinated hydrocarbon pesticides
Figure 4.
18
-------
SIMPLE AND AROMATIC CHLORINATED
HYDROCARBON PESTICIDES
PROCESS NO.1
Dichlorobenzene Chlorination Process
1.
Function - The dichlorobenzene chlorination process consists of
three process steps; the chlorination of the benzene, product re-
covery, and waste treatment and recovery.
In the chlorination step, dry benzene is charged into a lead or
glass-lined chlorinator containing about 1% by weight (of the ben-
zene charged) of iron turnings to be used as the catalyst. Chlorine
is then bubbled into the charge at the rate necessary to maintain a
constant temperature. This step yields waste HCl and chlorinated
benzene s .
To recover the dichlorobenzene, the chlorinated benzenes are neu-
tralized with an aqueous solution (10%) of caustic soda and then
sent to a separator. A sludge rich in dichlorobenzene settles out
and is withdrawn at the bottom. The lighter materials are with-
drawn and then distilled. The distillation yields benzene and
water, benzene and chlorobenzene, chlorobenzene, and dichloro- and
poylchlorobenzenes. The dichloro- and polychlorobenzelles and the
sludge are then processed for final re~0very of dichlorobenz~ne.
The basic waste product is the HCl by-product of the chlorination
process. This HCI is scrubbed with benzene or chlorobenzene and
then is absorbed in water to give hydrochloric acid. The benzene
or chlorobenzene from the scrubbing process is circulated into
the chlorination step of the process.
2.
Input Materials - Benzene and chlorine.
3.
Operating Parameters - Chlorination temperature, 40 to 60°C.
4.
Utilities - Data not available.
5.
Waste Streams - At one plant, liquid plant wastes containing poly-
chlorobenzenes go to an approved landfill.
6.
EPA Source Classification Code - None exists.
19
-------
7.
Reference -
von RUmker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-31l, Final Report, 15 March 1974.
20
-------
SIMPLE AND AROMATIC CHLORINATED
HYDROCARBON PESTICIDES
PROCESS NO.2
DDT Process
1.
Function - DDT is produced by the reaction of of chloral (or chloral
hydrate) and chlorobenzene in the presence of H2S04' The process
consists of four basic stages: the reaction, separation of DDT,
processing of DDT, and waste control and recovery.
In the two-stage reactor step, two moles of C6HSCl are reacted with
one mole of CCl3CHO with H2S04 as a catalyst to form DDT. In this
step, excess C6HSCl and the spent H2S04 along with the DDT are then
introduced to the DDT separator.
In the DDT separator, the DDT is extracted from the excess
and H2S04' There are two waste recovery streams from this
for H2S04 and one for C6HSCl. The product stream contains
purified and unprocessed DDT.
C6HSCl
step, one
the un-
The DDT processing step consists of several stages. First the DDT
is washed with NaOH and H20. The waste stream from this process con-
tains dilute caustic. The DDT then goes through a crystallizing,
drying, flaking stage from which it passes to either the packaging
or formulation process. At each stage through the final process-
ing there is some recovery of C6H5Cl.
The DDT process contains three waste recovery steps. One step re-
moves the C6HSCl from the separating and processing streams and re-
cycles it to the reaction step. The second step first removes the
acid from the separator stream. This acid is cycled through an acid
recovery plant from which the recovered acid is recycled to the in-
itial reaction step. The waste acid from the recovery plant is then
combined with the dilute caustic in a neutralizer. The final step
is the recovery of waste from clean-up operations.
2.
Input Materials - Chloral and chlorobenzene.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
S.
Waste Streams - Wastes resulting from the process include spent
hydrochloric and sulfuric acids, monochloral benzene, sodium mono-
chloral benzene sulfonate, chloral, NaOH caustic washwaters, chloro-
benzene, sulphonic acid, and some product. The waste streams may
21
-------
contain DDT in the 1-5 ppm range with DDE and other related compounds
present in amounts up to four times the DDT level. The pH of the
waste is low and the salt content is high. At one plant, the primary
waste stream containing waste acid and dilute caustic is neutralized
and sent to a Class I dump.
6.
EPA Source Classification Code - None exists
7.
References -
Atkins, Patrick R., The Pesticide Manufacturing Industry-Current
Waste Treatment and Disposal Practices, for U.S. EPA, Office of
Research and Monitoring, Project No. 12020 FYE, January 1972.
Lawless, E. W., R. von Rumker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-00-72-04, June 1972. NTIS Publication.
22
-------
SIMPLE AND AROMATIC CHLORINATED
HYDROCARBON PESTICIDES
PROCESS NO.3
Pentachlorophenol (PCP) Process
1.
Function - Pentachlorophenol is produced by the simple chlorination
of phenol in the presence of anhydrous aluminum chloride. The pro-
cess steps consist of a two-stage reaction and HCI recovery.
In the primary reactor, an excess of chlorine is added to phenol to
give the product pentachlorophenol. The wastes from this process
are cycled to the secondary reactor where more phenol is added. The
products of the second reactor are partially chlorinated phenols and
HCI. The phenols are recycled to the primary reactor, and the HCl
is recovered and cycled through a recovery process.
2.
Input Materials - Phenol and chlorine.
3.
Operating Parameters - Initial temperature of phenol, 65 to 130°C;
preferably 105°C.
- Atmospheric pressure.
- Reaction time varies from 5 to 15 hr.
4.
Utilities - Data not available.
5.
Waste Streams - At one plant, wastewater containing lower chlori-
nated phenols is sent to a treatment facility"
6.
EPA Source Classification Code - None exists.
7.
References -
Sittig, M., Pesticide Production Processes 1967, Noyes Development
Corporation, Park Ridge, New Jersey (1967).
von RUmker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality; Contract
EQC-3ll, Final Report, 15 March 1974.
23
-------
SIMPLE AND AROMATIC CHLORINATED
HYDROCARBON PESTICIDES
PROCESS NO.4
2,4-D Process
(2,4-Dichlorophenoxyacetic Acid)
1.
Function - 2,4-D is produced and recovered in a three-step process
with each step involving a distinct chemical reaction. First,
chloroacetic acid is combined with sodium hydroxide to obtain
ClCH2COONa. Thi& is combined with neutralized 2,4-dichlorophenol
in a condensation reactor to produce 2,4-D sodium salt. The salt
is then reacted with HCI to form 2,4-D and NaCI. The 2,4-D is then
recovered and cycled to a drying system. The NaCI is also r~covered.
At this same stage of the process, the excess dichlorophenol is re-
covered and returned to the condensation reactor.
There are three waste streams from the 2,4-D recovery step. At one
of the plants manufacturing 2,4-D, dusts are collected and recycled.
Liquid wastes are chemically treated, passed through a special trick-
ling filter, and then to a biological waste treatment plant. Solid
wastes, still bottomE, etc., are incinerated; the combustion gases
are scrubbed; the water is chemically treated, and then sent to a bio-
waste plant.
2.
Input Materials - 2,4-Dichlorophenol, chloroacetic acid, and NaOH.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
s.
Waste Streams - Waste streams from chlorinated hydrocarbon herbicides
such as 2,4-D include large amounts of sodium chloride, hydrochloric
acid, some caustic, and organics including solvents, phenols, chloro-
phenols and chlorophenoxy acids. These wastes arise from acidifica-
tion, washing steps, phase separation steps, incomplete yields and
chlorination of the phenolic compounds. A typical waste stream can
be characterized by:
COD
BODS
Total Solids
Suspended Solids
pH
8,300 mg/l
6,300
104,000
2,500
0.5
24
-------
Chlorides
Chlorophenols
Chlorophenoxy
Nitrogen
Phosphorus
Flow
Acids
52,000
112
235
Low
Low
30 # COD/# Product
The chlorinated herbicide wastes can vary considerably from plant to
plant and even in the same plant as indicated by the data in Table 3.
6.
EPA Source Classification CQde - None exists.
7.
References -
Atkins, Patrick R., The Pesticide Manufacturing Industry-Current
Waste Treatment and Disposal Practices, for U.S. EPA, Office of
Research and Monitoring, Project No. 12020 FYE, January 1972.
..
Lawless, E. W., R."von Rumker, and T. L. Ferguson, The Pollution
Potential in Pesticide }~nufacture, Midwest Research Institute for
the u.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-OO-72-04, June 1972. NTIS Publication.
Sittig, M., Pesticide Production Processes 1967, Noyes Development
Corporation, Park Ridge, New Jersey (1967).
von R~er, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-3l1, Final Report, 15 March 1974.
25
-------
N
0'\
Table 3.
WASTE CHARACTERISTICS OF CHLORINATED HERBICIDE WASTES~/
2, 4, 5-T Acid Waste 2, 4-D Acid Waste
Analysis
Sample 111 Sample 112 Sample 1/3 Sample 1/1 Sample 112 Sample 113
pH 7 . 5 7.9 8.5 9.5
COD (mg/1) 21,700 25,700 19,600 27,500 23,600 22,700
b/ b/ b/
BODs (mg/k)- 16,800 - 13,400 16,700 13,000
Chlorides (mg/1) 96,300 69,000 144,000 72,000
Total Solids (mg/1) 172,467 167,221
Total Volatile 18,150 22,100
Solids (mg/1)
Suspended Solids 700 348
(mg/l)
Volatile Suspended 242 83
Solids (mg/1)
Total Kje1dah1 40 45
Nitrogen (mg/l)
Odors Not Not
Offensive Offensive
~/
Source:
Patrick Atkins, The Pesticide Manufacturing Industry - Current Waste
Treatment and Disposal Practices, for u.S. EPA, Office of Research
and Monitoring, Project No. 12020 FYE, January 1972.
b/
16,680 mg/l using 50-50 dilution of 2, 4-D and 2, 4, 5-T and acclimated seed
(below toxic levels)
-------
SIMPLE AND AROMATIC CHLORINATED
HYDROCARBON PESTICIDES
PROCESS NO.5
2,4-DB Process
1.
Function - 2,4-Dichlorophenol, butyrolactone, and NaOH are combined
in a two-stage reaction to form 2,4-DB. The first reaction combines
the dichlorophenol and the sodium hydroxide to form alkali phenolate
according to the equation:
C12C6H30H + NaOH
)
Cl2C6H30Na + H20.
This product is then combined with the butyrolactone to produce
2,4-DB.
The 2,4-DB is then removed and cycled through a
The wastes from the reaction and the centrifuge
a recovery process to regain excess reactants.
cycled to the system.
centrifuge process.
are cycled through
These are then re-
2.
Input Materials - 2,4-Dichlorophenol, butyrolactone, and NaOH.
3.
50 to 200GC.
Operating Parameters
- First reaction temperature:
- pressure: atmospheric.
- time: 0.5 to 24.0 hr.
- Second reaction temperature:
- pressure: atmospheric.
- time: 1 to 6 hr.
135 to 210GC.
4.
Utilities - Data not available.
5.
Waste Streams - Data not available.
6.
EPA Source Classification Code - None exists.
7.
Reference -
U.S. Patent No. 3,076,025.
27
-------
SIMPLE AND ARO!-lA.TIC CHLORINATED
HYDROCARBON PESTICIDES
PROCESS NO.6
Toxaphene Process
1.
Function - Toxaphene is produced by chlorination of a-pinene (or
camphene). The a-pinene is reacted with a catalyst to form toxa-
phene solution. The solution is filtered and stripped to obtain
the toxaphene product. The chlorinator waste HCl gas passes through
a water absorber and the resulting muriatic acid is recovered or
neutralized and sent to wastewater treatment. The toxaphene prod-
uct then goes either to a solution or to a dust formulation step.
Emissions from the dust formulation are vented to a baghouse, with
the captured dust then recycled to the formulation step.
2.
a-pinene (or camphene) and chlorine.
Input Materials -
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - At one plant, the waste streams containing HCl are
treated before being discharged into a tidal creek.
6.
EPA Source Classification Code - None exists.
7.
References -
Lawless, E. W., R. von Rumker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-OO-72-04, June 1972. NTIS Publication.
..
von Rumker, R., E~ W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-3ll, Final Report, 15 March 1974.
28
-------
Diene-Based Chlorinated Pesticides
A large group of insecticides known as the diene-based group of chlori-
nated insecticides have been derived from hexachlorocyclopentadiene.
This group includes 13 pesticides: aldrin, dieldrin, heptachlor, chlor-
dane, isodrin, endrin, endosu1fan, isobenzan (telodrin), alodan, bromodan,
kepone, mirex, and pentac. Toxaphene has a similar chemical structure
and is sometimes grouped together with the dienes as the aldrin-toxaphene
group.
The structure of many diene pesticides is of the form:
@r~
where the Cl denotes a saturated chlorinated loop and A and Bare
side chains. A and B are quite often linked together to form another
loop, as indicated for some diene pesticides in Figure 5, which summar-
izes reaction sequences for diene insecticides.
The estimated annual production of diene group
cluded: aldrin (14 million pounds), chlordane
(7 million), endrin (4 million), endosu1fan (2
million), mirex (0.3 million), and kepone (0.1
pesticides in 1972 in-
(20 million), heptachlor
million), dieldrin (0.5
million) .
The production trend is downwards since aldrin
banned by the EPA because of high toxicity and
persistence. The uses of heptachlor have also
dane is being reviewed. Mirex, which received
ants, is also restricted by the EPA.
and dieldrin have been
low degradable, long-term
been callcelled and chI or..
widespread use for fire
The process flow diagram for the diene group is presented in Figure 6.
The hexachlorocyclopentadiene intermediate chemical used for all dienes
is produced from dicyclopentadiene with chlorination (Process 7). Most
of the diene pesticide processes include a Diels-Alder addition reaction
(Process 9) for direct synthesis or for synthesis of intermediate chem-
icals. The diene pesticide processes utilizing these intermediate chem-
icals are also indicated (Processes 10 through 13).
A typical waste stream from a diolefin based chlorinated hydrocarbon
pesticide manufacture will include:
COD
BODS
Total
So lids
500 mg/l
50
1,000
29
-------
Suspended
pH
Chlorides
Nitrates
Phosphates
Product
Toxicity
Flow
So lids
100 mg/l
2
High
?
?
100-300 ppb as Endrin
High
0.375 gallons treated
wastewater/# product
(This does not include concentrated liquids, tank
"bottoms", spent catalysts, etc., which are nor-
mally landfilled.)
Data on several of the processes within this industry segment were not
available in the literature. Therefore, detailed descriptions of these
processes were not prepared. These processes are:
Pentac Process
Kepone Process
Heptachlor Process
Endosulfan Process
Isobenzan Process
30
-------
~H~H
~H~H
r
~CH2OCOC"'3
~CH2OCOCHJ
:£' ~
~ lcf cY~'). ~
9 &if~i ~~o
v' 0 ~o H He.
CI2 PARTIAL ~
CS-HYDROCARBONS ----- CHLORINATION --.!:!.? 0
4.so.c--...
@ HEXACHLOROCYCLOPENTAOIENE
o~'-
A. '- ':d' 0' .ooj \. ,>":;
2. "20
~ ~C.O
~ ~ UOMODAN
!SODRIN
DIELDRIN
@Xl]
/0
@
f-a
~!
~H2
HEPTACHLOR
w
1-'-
~H
@ I
H H
CI
CHLORDANE
ALDRIN
CIO"12
DICYCLOPENTA
DIENE
r;\~
~
PENTAC
MIREX
"EPONE
E~OXIDATION
H~,
ENORIN
@XD>
~
ENDOSUliAN
SOC,, ...
H2
@!::>o
H2 .
IS08ENZAN
(TElOORIN)
ALOOAN
@1:"20
I@
H H2<=1
@ D P.rci>IOtlnat..! tl",
Figure 5. Synthesis of the diene group of chlorinated
insecticides--from hexachlorocyclopentadiene
-------
Prstieide kp'y'! v'
[ AICI3 0' C/2
H2C = CHCH2B,
CH2B, - HC = CHCH2B,
b;cyclo - (2.2. 1)-
2.5 heptadiene
]
[ ~7:~:i~d.'
8romodon
AloOon
Aldrin I
. Inter-nediate Chemicals
Ch lardene
Intermedi.;:te Inl='~
Cyclopenradirne
~CH20COCH3
~H20COCH3
CH20H - HC = CHCH20H
Alternote:
@
@D
Hel(oc:hloroc:yclo'"
pentcdiene Process
8
Acetylene or
Vinyl Chloride
Co
8
8
~
-B
=---e
Isobenzon Process
II Dieoe intil!'rrnediate chemicol~ from proces'e'L
.IV' Inpvh and product, are lined up respectively.
Figure
6.
Flow sheet
for diene-based pesticides processes
32
o
o
-------
DIENE-BASED CHLORINATED PESTICIDES
PROCESS NO.7
Hexachlorocyclopentadiene Process
1.
Function -Both hexachlorocyclopentadiene and cyclopentadiene are
produced in this process utilizing dicyclopentadiene. This is a
two-step process involving first a separation step and then a chlor-
ination step.
First, the dicyclopentadiene is heated in order to cause separation.
At this point, the cyclopentadiene is either recovered, or intro-
duced to chlorine and sodium hydroxide in the chlorination step.
The solvent for the chlorination is either CC14 or perchloroethyl-
ene. The product is then recovered as pentachlorocyclopentadiene.
The only waste stream in the process is after the chlorination step
and contains NaCl. This is cycled through a waste treatment system.
2.
Input Materials - Chlorine, sodium hydroxide, and dicyc1opentadiene.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - Water scrubber: Water + HeI.
- Chlorination: Water + NaCl.
6.
EPA Source Classification Code - None exists.
7.
Reference -
Lawless, E. W., R. von Rurnker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-OO-72-04, June 1972.
33
-------
DIENE-BASED CHLORINATED PESTICIDES
PROCESS NO.8
Hexachlorocyclopentadiene Process (alternate)
1.
Function - Hexachlorocyclopentadiene is produced by the chlorina-
tion of ~-pentane in this process. The basic steps are the reac-
tion, a heat exchange, and the product recovery.
The chlorine and ~-pentane are introduced into a burner reactor in
the presence of an anhydrous H2S04 catalyst. The chlorinated prod-
ucts then pass through a heat exchanger and into the product absorp-
tion column. The solvent in the column is either CC14 or perchloro-
ethylene. After the absorption step the stream is passed to a
distillation unit for recovery of the hexachlorocyclopentadiene.
2.
Input Materials - Chlorine and ~-pentane.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - H2S04 Dryer: H2S04 and H20.
- Water scrubber: HCl and H20.
6.
EPA Source Classification Code - None exists.
7.
Reference -
Sittig, M., Pesticide Production Processes 1967, Noyes Data Corpora-
tion (1967).
34
-------
DIENE-BASED CHLORINATED PESTICIDES
PROCESS NO.9
Diene Process, Aldrin
1.
Function - Aldrin is produced by reacting hexachlorocyclopentadiene
and bicyclo-(2.2.l)-2,5-heptadiene. The process includes a reaction
step in which the CSC16 and the C7HS are combined and a solvent
stripper step in which the aldrin and excess C7HSare separated.
The wastes are treated and passed to an asphalt-lined evaporation
basin at one plant.
2.
Input Materials - Hexachlorocyclopentadiene and bicyclo-(2.2.1)-
2,5-heptadiene.
3.
Operating Parameters - Reaction
- Reaction
- Reaction
temperature: 80 to 150°C.
pressure: Atmospheric.
time: Batch - 18 hr.
Continuous - 4 to 8 hr.
4.
Utilities - Data not available.
5.
Waste Streams - Liquid
solubility are sent to
plant.
waste containing aldrin to the level of
an asphalt-lined evaporation basin at one
6.
EPA Source Classification Code - None exists.
7.
References -
Lawless, E. W., R. von Rumker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-00-72-04, June 1972.
von R~er, R., E. W Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-31l, Final Report, 15 March 1974.
35
-------
DIENE-BASED CHLORINATED PESTICIDES
PROCESS NO. 10
Isodrin Process
1.
Function - Isodrin is produced by a two-stage reaction using hexa-
chlorocyclopentadiene, acetylene, and cyclopentadiene. The first
stage is the Diels-Alder condensation reaction of hexachlorocyclo-
pentadiene and acetylene as indicated in Process No.9. The second
stage is the condensation reaction of the Diels-Alder product and
cyclopentadiene to form isodrin.
2.
Input Materials - Hexachlorocyclopentadiene, acetylene (or vinyl
chloride), and cyclopentadiene.
3.
Operating Parameters - Diels-Alder condensation:
Temperature: 150 to 175°C.
Pressure: 2,000 to 4,000 psi with acetylene.
Reaction time: 0.5 to 3.0 hr.
Phase: Liquid, no solvent.
Equipment: Special design reactor.
- Isodrin condensation:
Temperature: 50 to 90°C (exothermic).
Reaction time: 2 hr after gradual reactant
addition.
Phase: Liquid, no solvent.
Equipment: Stirred, jacketed kettle with
reflux condenser.
4.
Utilities - Data not available.
5.
~aste Streams - Waste streams probably contain some amounts of HC1.
6.
EPA Source Classification Code - None exists.
7.
Reference -
Sittig, M., Pesticide Production Processes 1967, Noyes Data Corpora-
tion (1967).
36
-------
DIENE-BASED CHLORINATED PESTICIDES
PROCESS NO. U
Endrin Process
1.
Function - Endrin is formed by the addition of isodrin to HZOZ and
acetic acid in an epoxidation reaction.
2.
Input Materials - Isodrin, hydrogen peroxide, and acetic acid.
3.
- Temperature: 20 to 45°C, mildly exothermic.
- Pressure: Atmospheric.
- Reaction time: Agitated at length, then
heated to 45°C for 1 hr.
- Phase: Benzene solvent.
- Equipment: Stirred, jacketed tank.
Operating Parameters
4.
Utilities - Data not available.
5.
Waste Streams - Waste streams containing peracid, carboxylic acid
and benzene are steam washed and discharged.
6.
EPA Source Classification Code - None exists.
7.
Reference -
Sittig, M., Pesticide Production Processes 1967, Noyes Data Corpora-
tion (1967).
37
-------
DIENE-BASED CHLORINATED PESTICIDES
PROCESS NO. 12,
Dieldrin Process
1.
Function - Dieldrin is formed by the reaction of aldrin, hydrogen
peroxide, and acetic acid. The steps of the process include a mix-
ing stage, the reaction step, and product recovery.
In the mixing stage, the HZOZ and CH3COOH are mixed to form "per"
acid and aldrin is dissolved in a toluene solution. These two so-
lutions are combined in an oxidation reactor with HZS04 as a catalyst.
The dieldrin solution then is passed through normal extraction and
solvent stripping steps.
The waste streams from these process steps are sent to an evapora-
tion basin.
Z.
Input Materials - Aldrin, hydrogen peroxide, and acetic acid.
3.
Operating Parameters - Temperature: 0 to 75°C.
- Pressure: Atmospheric.
- Reaction time: 1 to 6 hr.
- Equipment: Mixing tank, first-stage reactor,
settling drum, second-stage re-
actor, third-stage epoxidation
reactor. Acids and water soluble
material are extracted with water.
Raffinate goes to still to recover
solvent and product.
4.
Utilities - Data not available.
5.
Waste Streams - Acids and water soluble materials are sent to an
evaporation basin.
6.
EPA Source Classification Code - None exists.
7.
References -
Lawless, E. W., R. von R~mker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-OO-7Z-04, June 197Z.
Sittig, M., Pesticide Production Processes 1967, Noyes Data Corpora-
tion (1967).
38
-------
DIENE-BASED CHLORINATED PESTICIDES
PROCESS NO. 13
Chlordane Process
1.
Function - Chlordane is produced by the chlorination of the inter-
mediate chlordene. (See Figure 6, Process No.9). The process
involves three major steps: S02C12 generation, the chlorination,
and product recovery.
In the first step, S02 and C12 are combined to form sulfurylchlor-
ide. An excess of S02C12 is then combined with chlordene in a
chlorination reaction. The resultant product stream contains a mix-
ture of chlordane, S02C12 and S02' The chlordane is removed and
processed, and the S02C12 and S02 are recycled to the S02C12 genera-
tion.
2.
Input Materials - Chlordene (or hexachlorocyclopentadiene and cyclo-
pentadiene) and C12'
3.
~ 69°C, reflux temperature of
sulfurylchloride.
- Pressure: Atmospheric.
- Reaction time: 1 hr.
- Equipment: Stirred, jacketed kettle equipped
with reflux condenser.
Operating Parameters - Temperature:
4.
Utilities - Data not available.
5.
Waste Streams - Spent hypochlorite.
ppm hexachlorocyclopentadiene. This
jected at one plant.
Wastewater is 2% NaOH and 400
wastewater is deep-well in-
6.
EPA Source Classification Code - None exists.
7.
References -
Lawless, E. W., R. von R~er, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-00-72-04, June 1972.
39
-------
..
von Rumker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-31l, Final Report, 15 March 1974.
Sittig, M., Pesticide Production Processes 1967, Noyes Data Corpora-
tion (1967).
40
-------
Organophosphate Pesticides
The organophosphate pesticides are hydrocarbon compounds which contain
one or more phosphorous atoms. The typical structure of acyclic organo-
phosphate pesticides is illustrated in Table 4 along with a tabulation
of many pesticides. Similarly, Table 5 presents the structure and tabu-
lated cyclic organophosphate pesticides.
The organophosphates can be separated into three main groups: (a) those
derived from phosphorus pentasulfide (P2SS)' (b) those derived from thio-
phosphoryl chloride (PSC13)' and (c) those derived from phosphorus tri-
chloride (PC13)' The chemical reactions and their relationships for key
pesticides in these three groups are presented in Figures 7, 8, and 9,
respectively.
Most organophosphates are used as insecticides with a few used as herbi-
cides. The acyclic insecticides include methyl parathion at 13 million
pounds and diazinon at 10 million pounds. The cyclic insecticides include
malathion at 2S million pounds. The herbicides include DEF at S million
pounds and merphos at 2 million pounds. The production of organophosphate
pesticides has increased since 1972.
The flow sheets for the organophosphate pesticide processes are presented
by groups in Figures 10 and 11. When similar reactions are involved and
similar chemical structures are formed, the related pesticide processes
are represented by one process block. Note that the pesticides formed
from PSCl3 can also be formed from P2SS by simple chlorination of the
P2SS or the intermediate mercaptan chemicals. The process blocks are
discussed in more detail in the individual process summaries that follow.
Data for several processes within this segment were not available, and
detailed descriptions of these processes were not included. These pro-
cesses include:
Dia1kyl Phosphorodithioic Acids
Na Substitution Process
Chlorination Process
C1 Replacement Addition Process
Ronnel Process
Trich10rfan Process
Dichlorios Process
Na1ed Process
Organophosphate Addition Process
Chlorine Tri-Addition Organophosphate
P-Tri-Addition Merphos Process
Process
41
-------
Table 4.
THE CHEHICAL STRUCTURE OF ACYCLIC ORGANOPHOSPHATE PESTICIDES
1. Monophosphorus
B Me = methyl
(A) -~-C-D Et = ethyl
Z
A B C D
(Systox) ~ Eta S a CHZCHZSCZHS
Demeton (mixture) ~ Eta a S CHZCHZSCZHS
Dichlorvos Mea a a CH = CCl
Z
Dicrotophos Mea a a C(CH3) = CHCON(CH3)Z
Dimethoate Mea S S CHZCONHCH3
Disulfoton Eta S S C~CHzSCZHS
Malathion Mea S S CHCOOCZHS
f
CHZCOOCZHS
Mevinphos Mea a a C(CH3) = CHCON(CH3)Z
Monitor Mea and MeS a ~
Monocrotophos Mea a a C(CH3) = CHCONHCH3
Naled Mea. a a CHBrCBrClZ
..;tMeO S a CHZCHZSCZHS
Oxydemeton-methyl (mixture)
(Meta-systox) ~MeO a S CHzCHZSCZHS
Phorate (Thimet) Eta S S CHZSCZHS
Phosphamidon MeO a a C(CH3) = CClCON(CZHS)Z
Trichlorfon Mea a CH(OH)CC13
42
-------
Table 4.
(Cone luded)
II. Diphosphorus
F H
II "
(E)2-P-G-P-(J)2
E F G H I
Aspon C3H70 S 0 S C3H70
Ethion EtO S SC~S S EtO
TEPP EtO 0 0 0 EtO
43
-------
Tabl. S.
!HE C1iEXICAL STRlIC'!URE OF CYCLIC ORGA.'OPHOSPHAn: PESTICIDES
I. SUbltttute-d phenyl.
@-8-~-D
A
~
-L
Carbopheoothtotl
c. -c:h lorophel1Y 1
s~s
(CB3)C1iOCCH . C(C1iJ)O
CrQtoxyph08
pheoyl
Cruf01l:lll te
4- Co. buty 1.2 -c:b lorophcnyl
Dylcmate (toonofo.)
phony I
FeD8ulfoc:trion (Cas.nit:)
4- {me thy hulftnyl )phenyl
°
Fenthion
4..thy Ithio-!-c:rellol
°
liediyl parathion
4..niCrophenyl
Parathion
4-n1trophenyl
FeDch lorpholJ (Ronne 1)
2.4,S.trichlorophenyl
°
D1capthon
2 -ch 101'0-4. n1 troph enyl
°
ramaphol
N ,N-d1tD1!!chy I-phenyl-4-
lulfona:a:1de
°
II. Two d1phollphorou!l COClp~o.d.
Ab. ce
(CH30)2 ~-oOsOoj
( ~
-SP(OC2HS)
)-S~(~RS)~
A2J-C-D
(OCH3)2
D1oxath1on
lIt. Other Cyclic Structures
-L -1- -L.
Azinpholl"mechyl (CuthLon) ~O
uinphos-echyl ~HSO
Dunban ~HSO °
Coum&pho. C2HSO °
Diaz1non ~HSO 0
Phoamet (lm1dln)
CRJO
44
-1-
-'L
-L.
o
(~HS)2
(OCH3)2
(I) OCHJ
(1) RROiJ
(1) OC2HS
(1) ~RS
(OC2HS)2
(OCHJ)2
(OCH3)2
(~HS)2
(~)2
(OCH3)2
(OCIIJ)2
-'L
~-lM
~-~
N
~~~
N
~~
J
CHJ
("""N
N~CH(CH3)2
-~-)-ra
'g~
-------
5
II
(CH30)2P - SCHCOOC2HS
I
CH2COOC2HS
Malathion
5 °
O~o (CH30)2~ - SCH2 - ~::MII 0
V) V) N~
~~ ~ N
~"~ df'L- \'=-' ~ A,rophoo-me
-------
S °
I .
(CH30)2 P - OCH2CH2SC2HS and (CH30h P - SCH~H2SC2HS
O"ydemetan (Meta Sylla,,)
s S
(CH30)2 ~ - o-@-S-@-O - P (QCH3h
Abate
J:
°
N
J:
U
N
J:
U
'"
..,
J:
N
U
S
(CH30)2 ~ - 0-@-SCH3
CH3
Fenthion
c...---
S
(CHJO)2 P - o-@-N02
Methyl Parathion
S
.
(CH30h P - CI
fCI2
S
.
(CH30h P - SH
5
0. II
:,.o~ (C2HSOh P - SH
;;'0-5- 1CI2
5
.
(C2HSOh P - CI =
5
- (CH30h ~ - 0-\QrN02
CI
Dicopthon
NaOH + HO-"Q\
\::::yS02N(CH3)2 ~ \ '? "CH3
-- (CH30h P - o-@- S - N,
o CH3
Famophos
S °
. n
(C2HSOh P - OCH2CH2SC2HS and (C2HSO)2 P - SCH~H2SC2HS
~ (S15Io")
!!ff
!->
.~
'-"
:!:-
,,'
""
0-
a
."
""
'"
:'.
iD
~
CI S cr
C1-o-0P~
CI CI
\!
Coumaphos
Diozinon
CI 5
-P- II OCH3
ClOP"
,
CI OCH3
5
.
(C2HSO) P - O-@-N02
Earothion
~\
S °
I II
(C2HSOh P - o-@-S - CH3
Fensulfothion (Dosanit)
5
.
(C3HP)2 P - CI
CSHSN,Na2C03
.
S
I
(C3HP)2 - P - 0- P(C3HPh
. Aspon
Figure 8.
Chemical reactions for organophosphate pesticides
from phosphorus trichlorosulfide
46
-------
°
II C/3CCHo.
(CH30)2 PH ..
°
II
(CH30h P - CH(OH)CC/3
Trichlorfon
!-CI.-H
°
II
< CH30)2 P - OCH = CCI2
Dich/orvos
Br2
II
.j::--
"
(CH30}JP
Trimethyl
Phosphite
l-~-
11t\eth'J . de
di1t\eth'J ceta1t\1..
..., N- etOa
1.'<. chlo-rac
N N-dimethylffiethyl-~-
, chloroacetoacetamlne
-
Heth
Yl-2-Chl
Ol-oaceto
acetat
. e
° °
II II
CH3C - CC/2 - C - N(C2H5h -
° f °
II II
5CI3 + CH3C - CH2 - CN(C2H5>2
CI 5 CI
;=\ 11/
CI:)J'0P,
CI C/
2NaOCH3 ;=\C/ ~/OCH3
. CI~OP,
C I OC 1-13
Ronnel
2,4,5-lrichloropheny/
di ch /orophosphate
Figure 9. Chemical reactions
°
II
(CH30h P - OCHBrCBrCI2
Naled
° °
II II
(CH30)2 P - OC(CH3) = CHCN(CH3h
Dicrotophos
° °
II II
.. (CH30)2P - OC(CH3) = CHCNHCH3
Monocrotophos
°
II
(CH30)2 P OC(CH3) = CHCOOCH3 (cis and trans mixture)
Mevinphos (Phosdrin)
..
° °
II II
(CH30>2 P - OC(CH3) = CC/CN(C2H5h
Phosphamidon
for organophosphate pesticides from other phosphorous compounds
-------
(2 rroles)
Figure
2HCI
Addition
Process
No Replacement
Organophosphate
Process 15
NaC/
a[ n-methyl-a chloroacetamide ] a[Dimethoate J
b[CIC2H4SC2H5 ] brDiSu1foton J
4-chlorephenyl-chloramethyl sulfide LCarbophenathion
H Replacement
Organophosphate
Process
14
H20
a[diethYlmaleote ]
n-ch loremethy Iben..a mi de
n-ch loremethylphta I imide
b [ HCHO + C2H5SH 1
CH2B'2
2.3-dichlore-p-dioxane
n-chloremethylben:
-------
T ri ch lorfon
Process
CH3CI
N, N-dimethylmethyl-2-
ch loroacetoacetamide
N, N-dimethylmethyl-2-
chloroacetoacetami ne
Methy 1- 2-ch loroacetoace tate
5CI3 + Acetoacetic Acid
Diethylamide
Chlorine
T ri-addition
Organophosphate
Process
[Phosphorous Oxych loridel
Phosphorous T ri ch loride J
P-tri-addition
Merphos Process
(Alternate)
Dichlorvas Process
(Alternate)
CH3CI
3HCI
(Alternate Process)
HCI
Naled Process
[DicrotoPhoS J
Monocrotophos
Mevinphos (Phosdrin)
Phosphomi don
[DEF J
Merphos
Figure 11.
Flow sheet for other organophosphate pesticide processes
49
-------
ORGANOPHOSPHATE PESTICIDES
PROCESS NO. 14
H-Rep1acement Organophosphate Process, Malathion
1.
Function - Malathion is manufactured in this process by the reaction
of dimethylphosphorodithioic acid and diethylmaleate or diethyl-
fumarate. This reaction is the first step in the malathion process.
The products of the reaction are first passed through a stripper
and then through a NaOH wash. The product is then passed through
a steam stripper and filter from which technical malathion is ob-
tained.
2.
Input Materials - Dimethylphosphorodithioic
(DEM) or diethylfumarate (DEF).
and diethylmaleate
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - The gas stream contains H2S which is processed for
sulfur recovery. The liquid stream contains NaCl. The wastewater
from the strippers and the waste stream from the NaOH wash is barged
to sea at one plant.
6.
EPA Source Classification Code - 3-01-033-01.
7.
References -
Lawless, E. W., R. von Rumker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-00-72-04, June 1972.
von Rumker, R., E., W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-3l1, Final Report, 15 March 1974.
50
-------
ORGANOPHOSPHATE PESTICIDES
PROCESS NO. 15
Na Replacement Organophosphate Process, Disulfoton
1.
Function - Disulfoton is produced by the reaction of sodium diethyl-
phosphorodithioate (diethyl salt) and ~-chloroethyl thioethyl ether
(chloro thio alcohol). In the Chemagro plant at Kansas City, Missouri,
where disulfoton is manufactured, intermediates are also produced.
The diethyl salt and chloro thio ether are combined in the presence
of NaOH in order to maintain caustic conditions. The reaction pro-
ceeds according to the equation:
(C2HSO)2P(S)SNa + CIC2~-S-C2H5 -7 (C2Hs0)2P(S)-S-C2H4-S-C2H5 + NaCl
The disulfoton is then recovered.
ered and recycled to the reaction.
The intermediates are also recov-
2.
Input Materials - Sodium diethylphosphorodithioate and ~-chloroethyl
thioethyl ether.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
to flare. Vents to atmosphere.
Triester and organic skimmings to burial.
Process wastewater to toluene extractor
and skimmer with final NaOH and NaOCI
treatment before flowing to the waste-
water treatment plant. Caustic condi-
tions (lime) remove some of the organo-
phosphates during a retention period of
36 hr. The pH is also adjusted and
polyelectrolyte flocculents added. The
effluent is discharged into the Blue
River with contaminants in the parts
per million range.
Waste Streams - Gas: HZS
- Liquids:
6.
EPA Source Classification Code - None exists.
51
-------
7.
References -
Lawless, E. W., R. von Rumker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-00-72-04, June 1972.
von RUmker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-311, Final Report, 15 March 1974.
Sittig, M., Pesticide Production Processes 1967, Noyes Data Corpora-
tion, Park Ridge, New Jersey (1967).
52
-------
ORGANOPHOSPHATE PESTICIDES
PROCESS NO. 16
Cl Replacement Organophosphate Process, Methyl Parathion
1.
Function - Methyl parathion is produced by the reaction of £,£-
dimethylphosphorochloridothionate and sodium £-nitro-phenoxide in
a batch process. The reaction of the chloridothionate and NaOC6P~N02
in the presence of acetone yields parathion and a waste stream con-
taining NaCl. The waste stream is treated with Na2C03'
2.
Input Materials - £,£-Dimethylphosphorochloridothionate and sodium
£-nitro-phenoxide.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
s.
Waste Streams - Liquid wastes from one plant, including by-product
HCl-NaCl, go to biological treatment facilities and then into a
sewer system. By-product H2S is flared, sulfur and waste solvent
are burned. The only solid waste is sludge from the biological
oxidation system which is recycled and discharged at a slow rate
into the sewer. Spills are washed into the waste treatment system.
6.
EPA Source Classification Code - None exists.
7.
References -
Lawless, E. W., R. von RUmker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-OO-72-04, June 1972.
von R~mker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-31l, Final Report, 15 March 1974.
53
-------
ORGANOPHOSPHATE PESTICIDES
PROCESS NO. 17
CI Replacement Organophosphate Process, Parathion
Function - Parathion, a liquid organophosphate pesticide, is pro-
duced by the reaction of diethylphosphorochloridothionate and sodium
E-nitrophenate. At least one producer (Monsanto) uses the same equip-
ment for parathion as used for methyl parathion production (see the
preceding process description for methyl parathion).
1.
2.
Input Materials - Diethylphosphorochloridothionate and sodium .E.-
nitrophenate.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
Waste Streams - The waste streams from parathion manufacture may contain
sulfur, HCl, sodium chloride, sodium carbamate, trimethyl thiophosphate,
and other organics including paranitrophenol and small amounts of
product. A typical waste stream can be characterized by:
5.
COD
BOD
Total Solids
pH
Acidi ty
Sodium
Chlorides
Phosphates
Nitrates
Sulfates
Parathion
Calcium
3,000 mg/l
700
27,000
2.0
3,000
6,000
7,000
250
20
3,000
20
High
Gaseous emissions from parathion production contain significant
amounts of mercaptans including hydrogen sulfide. Concentrated
residues and tank bottoms must also be handled since they contain
large amounts of intermediates and some product. This portion of
the waste may be a slurry with a paste-like consistency which poses
severe handling problems but seldom enters the wastewater stream.
6.
EPA Source Classification Code - None exists
54
-------
7.
References -
Atkins, Patrick R., The Pesticide Manufacturing Industry-Current
Waste Treatment and Disposal Practices, for U.S. EPA, Office of
Research and Monitoring, Project No. 12020 FYE, January 1972.
..
Lawless, E. W., R. von Rumker, and T. L. Ferguson, T~e Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Hater Programs, Technical Studies Report
No. 1$-00-72-04, June 1972. NTIS Publication PB 213-782/3.
55
-------
ORGANOPHOSPHATE PESTICIDES
PROCESS NO. 18
Cl Replacement Organophosphate Process, Diazino~
1.
Function - Diazinon is produced by the reaction of diethylphosphoro-
chloridothionate [(CZH50)2P(S)Cl] and 2-isopropyl-4-methyl-6-hydrox-
pyrimidene with Na2C03' The process consists of two reaction steps,
a purification and recovery step, and the waste treatment system.
The first reaction is a coupling reaction between the pyrimidene
and the (CZHs0)ZP(S)Cl, which is in a solvent such as toluene, benz-
ene or dioxane. The product of this reaction is then combined with
NaZC03 in a purification and filtration step. The product stream
then passes to a stripper and then a filtration step for collection
of the diazinon product.
2.
Input Materials - Diethylphosphorochloridothionate, Z-isopropyl-4-
methyl-6-hydroxpyrimidene, and NaZC03'
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - The two major waste streams from this process are at the
filtration steps. At one plant, the first waste stream containing NaCl
and NaHC03 is deep well injected. The waste stream from final filtra-
tion contains other organophosphates and is further processed.
6.
EPA Source Classification Code - None exists.
7.
~fu~oce-
von R~er, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council 'on Enviromental Quality, Contract
EQC-3ll, Final Rep~rt, 15 March 1974.
56
-------
Carbamate Pesticides
The carbamate family of pesticides includes over 30 pesticides with the
characteristic carbamate carbon-nitrogen structure (-N-C-). This family
can be separated into three groups: (a) the carbamate pesticides; (b)
the thiocarbamate pesticides; and (c) the dithiocarbamate acid salt pest-
icides.
The structure of the major carbamate and thiocarbamate pesticides is:
R 0
,211
Rl-N-C-R3
as summarized in Table 6.
The dithiocarbamate acid salts have the characteristic carbamate struc-
ture with two sulfur atoms added:
R2S
I II
RI-N-C-S-R3
as summarized below.
* * *
Pesticide Rl ~ R3
CDEC -C2Hs -C2H5 -CH2CCl=CH2
Dimethyl dithiocarbamic acid, K salt -CH3 -CH3 -K
Dimethyl dithiocarbamic acid, MIl salt -CH3 -CH3 =Mn
Ethylene bis(dithiocarbamic acid), =C2H4 -H -NH4
ammonia salt
Ferbam -CH3 -CH3 =Fe3
Maneb =C2~ -H =Mn
Metham-sodium -CH3 -H -Na
Nab am =C2~ -H -~
Zineb =C2H4 -H =Zn
The production of the carbamate family of pesticides in 1972 was esti-
mated at over 132 million pounds. The carbamate insecticides included
carbaryl at 53 million pounds and carbofuran at 6 million pounds. The
thiocarbamate herbicides included butylate at 6 million pounds and EPTC
*
Two of three bonds indicates connection with two or three thiocarba-
mate groups (Le., "=C2~n indicates "C2~ (thiQcarbamic acid salt
group)2")'
-_.~
'57'
-------
Table 6.
STRUCTURE OF CARBAMATE AND THIOCARBAHATE PESTICIDES
P"sticide
~z~
RI-N-C-R3
Rl RZ R *
3
-CH3 -H -ON=CH-(CH3)ZSCCH3
-@ -H -OCH ZC=CCH ZC 1
-CHZCH(CH3) z -CHZCH(CH3) z -SCZHS
-CH3 -H -to
:::-.. h
-CH3 -H ~
-? 0 (CH3) z
-@l -H -OCH(CH3)Z
D -CZHS -SCZHS
-CH(CH3)Z -CH(CH3)Z -SCHZCCl=CHCl
-C3H7 -C3H7 -SCZHS
Aldicarb
Ba rban
Butylate
Carbaryl
Carbofuran
Chloropropham
Cycloate
Di-Allate
EPTC
Metalkamate
Tri-Allate
(l)-hexamethyl- (Z) -SC ZHS
-nC4H9 -CZHS -SC3H7
-@ -H -CH(CH3)Z
-CH (CH3) Z -CH(CH3)Z -SCHZCCl=CClZ
-nC3H7 -nC3H) -SC3H7
Molinate
Pebulate
Propham
Vernolate
* Pesticides with S in the RJ group are thiocarbamates.
58'
-------
at 5 million pounds. And the dithiocarbamic acid salt fungicides in-
cluded maneb at 15 million pounds, zineb at 8 million, metham at 5 mil-
lion, and nabam at 4 million pounds. The carbamate family production
growth rate appears stable with potential for growth.
The chemical reactions for most carbamate-family pesticides are indi-
cated in Figure 12. Figure 13 is the flow sheet for carbamate and thio.
carbamate pesticide processes, and Figure 14 is the flow sheet for the
dithiocarbamic acid salt processes.
Data were not available for several processes within this industry
segment, and detailed process descriptions were not prepared. Those
processes are:
Thiocarbamate
Carbamic Acid
CDEC Process
Process
Salt Process
59
-------
Carbamate Pesticides (amine reaction):
R2
I
R1- N - H
amine
o
II
C I - C - R3
formate
(or phosge ne)
+
-
Thiocarbamate Pesticides:
R2 0
I II
R 1 - N - C - R3 +
carbomate pesticide
or intermediate
carbamyl chloride *
HCI
R2 0
I II
R1-N-C-CI
intermediate
carbamyl chloride *
R2 0
I II
R4S H - R 1 - N - C - S - R4
mercaptan thiocarbamate
or thiol pesticide
R2 S
I II
R30H - (Rl - N - C - S) R3
hydroxide ./carbamic acid
or NHy salt pesticides
Dithiocarbamic-Acid Salts (replacement):
~ /
(R 1 - N - C - 5)n R3 + R4CI
carbamic acid salt salt
pesticide (# 1) (Clor
sulfate)
+
Carbamate Pesticides (cyanate reaction):
Rl - NCO
cyanate
R50H -
alcohol
+
Dithiocarbamic-Acid Salts:
C52
R2
I
R1 - NH
amine
+
+
H 0
I II
R 1 - N - C - OR5
carbamate pesticide
R2 5
I II
. (R 1 - N - C - 5)x R4
carbamic acid salt
pesticide (# 2)
+
+
. . . . . (1)
HCI
. . . . . (2)
. . . . . (3)
+
H20. . . . . (4)
R3CI
salt
(Clor
sulfate)
. . . . (5)
Figure 12.
Typical chemical reactions to produce carbamate pesticides
60
-------
Amine Addition
Process
HC!
Amine
- methylamine carbaryl
~ N-ethylcyclahexylamine - cycloote
'\ hexamethyleneimine - molinate
di-n-propylamine - EPTC (alternate)
"" di-n-propylamine - verno late (alternate)
ethyl-n-butyla:ni ne - pebulate
~ aniline - propham, "IPC"
N-chloroaniline - chloropropham, "CIPC"
4-chloro-2-butynylchloroformote - 3-chloroanline - IxIrbon (alternate)
l-napthyl chloroformate
ethylch loroth ioformate
N-propych lorolh ioformate
isopropy leh loro forma te
Amine Addition
Process
HCI
Thioeorbomate
Process
HC)
Amine
di-n-propylamine
Mercoptan or Thiol
- di-n-propyl-cc ~ ethyl mercaptan
N-propyl mercaptan
di-isobutyl-cc ethyl mercaptan
ethyl-n-butyl-cc - N-propyl mercaptan
di-isopropyl-cc ~ 2,3-dichloropropenyl-l-thiol -
2.3. 3-trichloropropenyl-l-thiol -
EPTC
vernoJate
butylate
pebvlate
di-allate
tri-al'ate
di-isobutylamine
ethyl-n-butylamine -
di-isopropylami ne
Carbamate
Process
Alcohol
~ 2, 3-dihydro-2, 2-dimethyl-7-benzofurono! - carbofuran
CH3SC(CH3)2 CH = NOH - aldicarb
CSH 11-@-OH - bux
chlorophenyl isocyanote - 4-chloro-2-butynol - barbon, "corbyne"
methyl isocyonote
.. Intermediate Chemicals
Figure 13.
Flow sheet for carbamate pesticide processes
61
-------
Carbamic Acid
Salt Process
Amine
potassium hydroxide- dimethy/amine - dimethyldithiocarbamic acid. K selt
sodium hydroxide - methylamine - metham - sodium
ammonia - ethylenediomine- ethylene bis(dithiocarbamic acid). ammonia salt
Carbamic Acid
So I t Process
Figure 14.
Carbamic Acid
Salt Replacement
Process 21
Carbamic Acid
Salt Replacement
Process
Carbamic Acid
Salt Replacement
Process
Carbamic Acid
Salt Replacement
Process
CDEC Process
Flow sheet for dithiocarbarnic acid salt pesticide processes
62
-------
CARBAMATE PESTICIDES
PROCESS NO. 19
Amine Addition Process, Carbaryl
1.
Function - Carbaryl is produced by the reaction of l-naphthol,
COCl2' NaOH, and methylamine. The process consists of two reac-
tion steps, a product recovery step and waste removal.
The first reaction step combines naphthol, NaOH, and COCl2 to form
I-naphthyl-chloroformate and waste NaCl. The naphthyl-chloroformate
is then introduced with NaOH and CE3NHz to the carbaryl unit. This
reaction produces carbaryl and NaCl waste. The reaction chemistry
for this process is:
~
~
O-C(O)Cl
~ CH3~
~ NaOH >
~(O)NHCH3
LJ0
COCl2
NaOH )
I-Naphthol
l-Naphthyl-
chloroformate
Carbaryl
The carbaryl is then dried and packaged.
2.
Input Materials - l-Naphthol, COCl2, NaOH, and methylamine.
3.
Ope~ating Parameters - Data not available.
4.
Utilities - Data not available.
s.
Waste Streams - Considerable care, through the use of special scrubbers
and by enforcing safety precautions, must be taken to ensure that
phosgene does not escape to the atmosphere. Wastewaters contain high
total solids but almost no suspended solids and little pesticidal
compounds. A typical waste stream from carbamate manufacture will
contain:
COD
BODS
Total Solids
pH
Suspended Solids
Sodium
10,000 mg/l
Nil
40,000
7-10
Nil
8,000
63
-------
Chlorides
Phosphates
Organic Nitrogen
Sulfates
Product
Toxicity
Flow per pound of product
100 mg/l
Nil
500
20,000
Nil
Low
Not available
At one plant, all pesticide-containing wastewater goes to the plant's
secondary waste treatment system and then to a river. This effluent
contains only 0.01 to 1 ppm carbaryl. Toxic vents are either flared
or go to NaOH scrubbers. Nontoxic vents go to a condenser and are
then vented to the atmosphere. Standard hoods are used in the packaging
area and the recovered material is recycled. The heavy residue solid
wastes are burned. One shutdown for cleaning is made per year, but
numerous maintenance clean-ups are made and the washings go to the
process waste treatment system.
6.
EPA Source Classification Code - None exists.
7.
References -
Atkins, Patrick R., The Pesticide Manufacturing Industry-Current
Waste Treatment and Disposal Practices, .for U.S. EPA, Office of
Research and Monitoring, Project No. l2~20 FYE, January 1972.
Lawless, E. W., R. von R~mker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-00-72-04, June 1972. NTIS Publication PB 213-782/3.
64
-------
CARBAMATE PESTICIDES
PROCESS NO. 20
Carbamate Process, Carbofuran
1.
Function - Carbofuran is produced by the reaction of 2,3-dihydro-
2,2-dimethyl-7-benzofuranol and methyl isocyanate. The process
consists of the reaction of these two chemicals in the presence of
ether and (CH3)3N. The carbofuran is recovered from the products,
and the waste stream goes through neutralization, concentration
equalization, and settling before discharge.
2.
Input Materials - 2,3-Dihydro-2,2-dimethyl-7-benzofurano1 and methyl
isocyanate.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - Data not available.
6.
EPA Source Classification Code - None exists.
7.
Reference -
von R~mker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-311, Final Report, 15 March 1974.
65
-------
CARBAMATE PESTICIDES
PROCESS NO. 21
Carbamic Acid Salt Replacement Process, Maneb
1.
Function - Maneb is produced by the reaction of nabarn and manganese-
sulfate. A concentrated nabam solution is reacted with manganese-
sulfate, and the desired manganese ethy1enebisdithiocarbamate is pre-
cipitated. The slurry is washed with water to remove sodium sulfate
and dried to less than 1% water content. Process by-products include
sodium sulfate and small amounts of carbon disulfide and sodium hy-
droxide.
2.
Input Materials - Nabam and manganese sulfate.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - At one plant, liquid sulfidic wastes containing
Na2S04 are discharged to a municipal sewer system. Air emissions
are filtered and the resultant collected dust is landfilled.
6.
EPA Source Classification Code - None exists.
7.
Reference -
..
von Rumker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-311, Final Report, 15 March 1974.
66
-------
Triazine Pesticides
The derivatives of ~-triazine form an important class of herbicides.
Atrazine is by far the most widely used of all herbicides today. Dyrene
is used as a fungicide. The general structure is:
X
N~N
)lN~B
where A and B
as shown below.
cal order, e.g.,
B .)
are normally amine groups and X a less basic group
(Note: Numbering of the substituents is in alphabeti-
2-chloro but 6-methoxy with i-PrNH-groups at A and
A B X
Arne t ryne@ EtNH- i-PrNH- -SCH3
Atratone EtNH- i-PrNH- -OCH3
Atrazine EtNH- i-PrNH- -Cl
Bladex@ EtNH- (CH3)2C (CN)NH- -Cl
Chlorazine Et2N- Et2N- -Cl
Cyprazine CHzCHzCHN- (C~)2CHNH- -Cl
Dyrene@ ClC6~NH- Cl- -Cl
Igran 80\~(terbutryne) EtNH- (CH3)3CNH- -SCH3
MPMT CH30(CH2)3NH- CH30(CH2)3NH- - SCH3
Prometone i-PrNH- i-PrNH- -OCH3
Prometryne . i-PrNH- i-PrNH- -SCH3
Propazine i-PrNH- i-PrNH- -Cl
Simazine EtNH- EtNH- -Cl
Trietazine EtNH- EtNH- -Cl
The estimated U.S. annual production of triazine pesticides is about
110 million pounds. Atrazine is by far the most important pesticide
in this family with a current U.S. annual production of 95 million
pounds. Atrazine is produced by a continuous process. The inter-
mediate step of forming cyanuric ethylamine is combined in the amina-
tion unit in the continuous process (shown in Process 56 in Figure
16). Other triazine pesticides can be made in the same facility as
atrazine. The growth trend for the triazine pesticides is up slightly
as new appl~cations and mixtures are approved for atrazine.
67
-------
Cyanuric chloride is reacted with appropriate amino hydrocarbons to ob-
tain the different triazine pesticides. Reaction sequences for selected
triazine pesticides are shown in Figure 15. A general pro~ess flow sheet
for the synthesis of triazine pesticides is presented in Figure 16. The
cyanuric chloride ~7 produced from hydrogen cyanide and chlorine as de-
scribed by Sittig.- The cyanuric chloride unit and all other triazine
pesticide processes include a water wash of the pesticide product.
Data were not available on several processes within this industry seg-
ment. These processes for which descriptions are not included are:
Cyanuric Chloride Process
Dyrene Process
Cyanuric Ethylamine Process
Ametryne Process
Terbutryne Process
Propazine Process
Prometone Process
Prometryne Process
68
-------
L>y rcnc
9lCl
Stmszine
NH
~
C1JQ~1
CI
A
D
CZH )rrANd.l~licZH5
"", I
0;'
f Cl
~N CZI' )1,1[06 Ii" -C[I (CJI, ) 2
~N .~"'- ~
~...~-:..-! AtroJ,zint.:
0'/'
c<-~ '\. /
\:7
XII)
CH)SII In!
---.,. C ,II)NII J.....~,1H~1I (CI[ J ) c
Aml.!cryne
J[
"0"
j,,,~
CI .. Cl
CZH\N!IZ ).
y
NON
);N~
!...ZI1)NH Cl
Cy"nU<1C ~
CI. J Ot ide
(CII»ZCllhlIZ
Cl
~
(CiI) )ZCIIt~IQN!ICH ICH)2
(CH3) 3c:.1JZ
Cl
N~'
czIIstw19J NJlC(
-------
H20 Wash HCI + H20.
+ HCI.
HCI + H20.
Cyanuric
Ethylami ne
Process
H20 HCI + H20.
Atrazine
Process 22
H20
H20 + HCI.
r-\
(CH3)3CNH2
"'--/
(\
(CH3 )2CHNH
\..J
H20 HCI + H20.
H20 HC! + H20.
"HCI ,. H20 to pH Control Unit with NoOH, then to wastewater treatment.
Figure 16.
Flow sheet for triazine pesticide processes
70
-------
TRIAZINE PESTICIDES
PROCESS NO. 22
Atrazine Process
1.
Function - Atrazine is produced in a continuous process by the re-
action of cyanuric chloride, ethylamine, and (CH3)ZCHNHZ' The process
consists of the continuous reaction step, product recovery, and waste
handling.
In the reaction step, the ethylamine, (CH3)ZCHNHZ and a solvent are
added to the cyanuric chloride. The solvent is removed from the
unit and recycled to the process. The product stream is passed
through a filter and on. to the atrazine formulation unit. Here any
additives or solvents are combined with the atrazine and the final
product is then packaged.
2.
Input Materials - Cyanuric chloride, ethylamine, and (CH3)CHNHz'
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - The gaseous waste stream is scrubbed to remove HCI.
Scrubber water as well as the liquid wastes from the filtration and
formulation are treated and then discharged to a river.
Sanitary wastes from the pl~nt are chlorinated before they are dis-
charged. The BOD of the waste going to the river is 500 lb/day at
the 100 million pounds per year production rate.
Dusts are emitted in the formulation and packaging areas. Losses
are estimated to be less than 1%. Fabric filters or wet scrubbers
are employed to control dust emissions.
6.
EPA Source Classification Code - None exists.
7.
References -
Lawless, E. W., R. von Rurnker, and T: L. Ferguson, The Pollution
Potential in Pesticide ~anufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-00-72-04, June 1972.
von R~IDker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-311, Final Report, 15 March 1974.
71
-------
Anilide Pesticides
The anilide pesticides are a small group of four important herbicides.
These pesticides are derived from aniline with a general structure as
follows:
o
II
~*Rl-N-C-R~4
RO
5
~
Pesticide Rl R2 R3 R4 R5 ~
Alachlor CH30C~ C~Cl CzHs CZH5 H H
Butachlor C4~OCH2 CHzCl C2H5 C2H5 H H
Propachlor (CH3)2CH CHZCl H H H H
Propanil H C2H5 H H Cl Cl
The production of this small group of four anilide pesticides was esti-
mated at 71 million pounds in 1972 with individual production of alachlor
at 24 million pounds, butachlor at 5 million pounds, propachlor at 35 mil-
lion pounds and propanil at 7 million pounds. Propanil is the oldest
herbi~ide of the group, having been introduced in 1960 by Rohm and Haas.
The other three pesticides have been introduced since 1965 by the MOnsanto
Company (Monsanto also makes propanil). The growth trend in these pesti~
cides is upward with large gains possible for butachlor (introduced in
1969) .
The chemical
presented in
The chemical
are based on
reaction sequences for synthesis of these pesticides are
Figure 17, and a process flow sheet is shown in Figure 18.
reactions indicated for alachlor, butachlor, and propachlor
information obtained from Monsanto.
Detailed
industry
prepared
data were not available for some of the processes within this
segment. Therefore, detailed process descriptions were not
for the following processes:
Aniline Addition Process
Propanil Process
72
-------
NH2
C2H5l6(C2H5 H2CO
Solvent
Diethylani line
.......
W
NH2
6 H2CO
Solvent
Analine
~CI
CI
CH3CH2COOH .
50CI2
(Catalyst)
3.4-dichloroaniline
CH2
II
N
C2H5,&C2H5
CH2
II
N
6
°
I
H, /c - C2H5
~CI
CI
Proponil
Figure 17.
CICH2COCI
.
CICH2COCI
.
+H20
o
I
CH30CH2 .....c - CH2CI
'N"-
C2H5L6rC2H5
~\'\
(.\'\3 Alachlar
t-I\'\3
°
I
C.4H90CH2 /C - CH2CI
'N
C2H5,&C2H5
°
II
CICH2 ~C - CH2CI
'N'
C2H5L6rC2H5
o
M
CICH2' ....C - CH2CI
N
6
C..H90H
NH3 .
CH3CHOHCH3
.
NH3
+ NH..CI
+ NH4CI
Butach lor
o
II
CH3CHOCH3, ......c - CH2CI
N
H5C2,&C2H5
+NH..CI
Propach lor
Chemical reactions for production of anilide pesticides
-------
'-J
.po
Aniline Addition
Process
H20
Aniline InRut*.
[ diethyl aniline]
diethyl aniline
aniline
Propani I Process
H20
Figure 18.
Aniline Process
23
NH4CI
[ ~:~~::llnRut*]
butanol .
isopropanol
Pesticides*
[ alachlor ]
butach lor
propachlor
* The chemical inputs required for an individual pesticide
are in line across the flow sheet.
** The diethyl groups are not present for the aniline reaction.
Flow sheet for anilide pesticide processes
-------
ANILIDE PESTICIDES
Aniline Process, Alachlor
1.
PROCESS NO. 23
Function - Alachlor is produced by the reaction of diethyl(chloro-
methyl-chloroacetyl)anilide, anhydrous ammonia and methanol. The
process involves a reaction step, production formulation, and waste
handling.
First, the ammonia and methanol are added to the
combination. The reaction products are alachlor
The alachlor is withdrawn and passed to either a
or granule formulation unit. The waste NB4Cl is
waters and discharged with liquid effluent. The
and used as fuel.
2.
anilide and solvent
and waste NH4Cl.
liquid formulation
combined with waste-
solvent is recovered
Input Materials - Diethyl(chloromethyl-chloroacetyl)anilide, anhy-
drous ammonia, and methanol.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - The liquid effluent discharge contains H20 and NH4Cl.
6.
EPA Source Classification Code - None exists.
7.
Reference -
Lawless, E. W., R. von R~mker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-OO-72-04, June 1972.
75
-------
Urea and Uracil Pesticides
The urea and uracil pesticides include a group of about 25 pesticides
used as herbicides. These pesticides can be synthesized from urea as
a common base (as inferred by the classification). However, more fre-
quently, they are synthesized from an isocyanate compound. Phosgene is
used in the synthesis of most urea and uracil pesticides as indicated
in the chemical reaction steps in Figure 19.
Most urea pesticides have the common chemical structure of:
HO
R1TI-U-g_
-------
H 0
I n ,OCH3
CI)'Q}-N - C - N,
CI CH3
linuron ~ ~ <;> ,CH3
--- ~N-C-N
CF3 'CH3
--?<~t/'
7
~N = C = 0
CF3
,~,~ ~'lt-lo1)
~i\Cl' . c~~
o~o' ~
\,..:p' ,,'<'" @-
~ 0 N=C=O
/~
~_:,:~O\L.__.
4- (4-chlorophenoxy) aniline. CI-('0
t"-so:
?('O
~('
"'t
Fluometuran
H 0 H
~LI . /
\QrN - C - N
CH30
Siduron
~
-------
Table 7.
UREA PESTICIDES STRUCTURE
:@ H 0 RJ
0" " ;'
Rl 0 -N-C-N,
R2 R4
Pesticide Rl R2 R3 R4
Ch loroxuron -4-chlorophenoxy -H -CH3 -CH3
Diuron -Cl -Cl -CH3 -CH3
Fluometuron -H -CF3 -CH3 -CH3
Linuron -Cl -Cl -OCH3 -CH3
Monuron -Cl -H -CH3 -CH3
Monuron-TCA -COOCl3 -H -CH3 -CH3
Siduron -H -H -H -2-methycyclohexane
Other Area Pesticides:
(less sales)
Fenuron -H -H -CH3 -CH3
Neburon -Cl -Cl -CH -n-butyl
3
Buturon -Cl -H -CH3 -l-butyn-3-yl
Monolinuron -Cl -H - OCH3 -CH3
Metabromuron -Br -H -OCH3 -CH3
Ch lorobromuron -Br -Cl -OCH3 -CH3
Metoxuron -OCH -Cl -CH3 -CH3
3
78
-------
2. Heet
isocyanate
Proceu
2 HCI
Amine Addition
Process
1. Aniline isocyanate (iso) Amine Pesticide
[3, 4-dichlorooni line -3. .4-dichlorophenyl isocyanate - dimethylamine - Diuron ]
-""""0, N-dimethylhydraxylamine - Linuron
3-trifluoromethylaniline - 3-trifluoromethylphenyl iso. - dimethylamin
-------
Data were not available for several processes within
ment. Therefore, detailed process descriptions were
the following processes:
Isocyanate Process
Amine Addition Process
Monuron-TCA Process
Methyluracil Process
Terbacil Process
Urea Addition Process
80
this industry seg-
not prepared for
-------
UREA AND URACIL PESTICIDES
.
PROCESS NO.2 4
Bromaci1 Process
1.
Function - Bromaci1 is produced by the reaction of 3-sec-butyl-6-
methyl uracil and bromine. The 3-sec-butyl-6-methy1 uracil for the
process is produced using the Urea and Methyluracil Processes in the
same plant. The bromacil process consists of the bromination of the
uracil. The reaction chemistry is believed to be as follows:
o
It
sec-C4Hg N~
~~N~CH
I 3
H
pH 5.5
)
o
sec-C4H9 N~Br +
o'l~NR CH3
+ Br2
HER
The reaction step of the process consists of adding bromine and water
to the uracil. NaOH is then added to the product to neutralize the
solution. The product then goes through a filtration and drying step
where the bromacil is obtained.
2.
Input Materials - 3-Sec-butyl-6-methyl uracil and bromine.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - The NaBr waste stream is passed to a bromine re-
covery process.
6.
EPA Source Classification Code - None exists.
7.
Reference -
von R~mker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-3ll, Final Report, 15 March 1974.
81
-------
UREA AND URACIL PESTICIDES
PROCESS NO. 25
Amine Addition Process, Diuron
1.
Function - Diuron is produced by the reaction of 3,4-dich1oropheny1
urea and dimethy1amine. The 3,4-dich1oropheny1 urea in solvent is
mixed with the dimethylamine. The products of the reaction are waste
Nfl3 and crude diuron in solution. The product is then distilled to
obtain the crude diuron. The solvent from the distillation is re-
cycled to the process. The crude diuron is then dissolved in 30 to
35% HCl to remove impurities and then is precipitated with H2O.
2.
Input Materials - 3,4-Dichlorophenyl urea and dimethylamine.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - Aqueous waste contains some quantities of HCl.
6.
EPA Source Classification Code - None exists.
7.
Reference -
von R~mker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Cor-tract
EQC-3l1, Final Report, 15 March 1974.
82
-------
Nitrated Hyd~ocarbon Pesticides
The nitrated hydrocarbon pesticides include six pesticides with one or
two of the characteristic nitro (-NOZ) groups in their chemical struc-
ture. These pesticides include the dinitroaromatics (trifluralin, benefin,
dinoseb, and DNOC) and the chlorinated nitro hydrocarbons (nitrofen and
chloropicrin). The dinitroarow~tic pesticides and nitrofen are herbi-
cides. Chloropicrin is an insecticide.
The general structure of the nitroaromatic pesticides is:
Rl
~g~
R4
with the individual
" R"
groups indicated below.
Pesticide Rl R2 R3 ~ RS R6
Dinoseb -OR -CR(CR3)CRZCH3 -H -NOZ -R - ~T() 2
DNOC -OR -CH3 -H -NOZ -R -NOZ
Trifluralin -N(CH2CHZCH3)2 -NOZ -H -CF3 -H -NOZ
Benefin -CH3CHZNCH2CHZCH2CH3 -NOZ -H -CF3 -H -NOZ
-0
Nitrofen qCI -H -H -ooZ -H -H
The estimated production of the nitrated hydrocarbon pesticides in 197Z
was 33 million pounds. Trifluralin was the most popular herbicide in
the group at Zl million pounds followed by dinoseb at 3 million pounds,
and benefin at Z million pounds. The production of chloropicrin, an in-
secticide,was about 5 million pounds.
The chemical reactions for the dinitroaromatic and other nitrated hydro-
carbon pesticides are indicated in Figure Zl. In addition, the process
flow sheet is presented in Figure ZZ. The dinitroaromatic pesticides
(all) incorporate the nitration process as shown in Figure 22. Trifluralin
and bene fin also include an additional amine addition process (Process 26
and 27. The input materials for nitrofen and chloropicrin are already
83
-------
CH3CHZCHZ - N - CHZCHZCH3
OZNVNO
2
C't\:)7. 0
~,-(C't\7.C't\~ Triflurolin
CI ~CO'j CF3
NOZ '* NOZ ~
o CHJCHJ- NH- C CH3CHZ ~- N - CHZCHZCH2CH3
CF ... H2CH ° N
0H 3 N02COJ 2CH2CHJ Z 0 NOZ
@- CH (CH
JJcH2CH CF3
3 OH
0-s- OZNir CH (CH3)CHZCH3
~ 0
~ C'-s:
;,y NOZ Dinoseb
Benefin
-
CI
OH
*CH3
~ DNOC
NOZ
CI
$ --- CI~O-@-N02
CI Nitrofen
NOZ
OH
J:yCI
~ +
CIZ + NoOH + CH3NOZ
-...
CCI3 NOZ
Chloropicrin
Figure 21.
Chemical reactions to produce the nitrated
hydrocarbon pesticides
84
-------
Ni trotion
Process
H2S04 + H20
~- -sec-butylphenol - ---- - ---- - -------Ginosebj
<2-creso I+H 2S0 4
chloro-4-trifluoro- ------------------- DNOC
metylbenzene
Triflurolin
Process
26
+ NoCI
Benefin
Process
27
Figure 22.
Flow sheet for nitrated hydrocarbon pesticide processes
NoCI
Nitrofen
Process
H20
85
-------
nitrated with one nitro group each. Thus, the nitrofen process is an
addition reaction and the chloropicrin process is a chlorination reaction.
Detailed process descriptions were not prepared for those processes for
which data were not available. Those processes are:
Nitration Process
Chloropicrin Process
86
-------
NIT~~TED HYDROCARBON PESTICIDES
PROCESS NO. 26
Trifluralin Process
1.
Function - Trifluralin is produced by the reaction of 2,6-dinitro-
l-chloro-4-trifluoromethylbenzene and dipropylamine with sodium
carbamate. In some cases, the 2,6-dinitro-l-chloro-4-trifluoro-
methylbenzene is produced as shown in Figure 22 as a part of the
same manufacturing process.
The trifluralin process consists of the addition of sodium carba-
mate, dipropylamine, and water to the dinitro in CRC13 solvent. The
products of the reaction are first filtered and then decanted to re-
move the saltwater waste. The crude trifluralin is then distilled
in a vacuum still with aromatic naphtha and the resulting streams
are technical grade trifluralin and CRC13' The CRC13 is recycled
to the process.
2.
Input Materials - Chloro-4-trifluoromethylbenzene and HN03/~S04
(or 2,6-dinitro-l-chloro-4-trifluoromethylbenzene) and dipropylene
with sodium carbamate.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - The wastewaters contain NaCl.
6.
EPA Source Classification Code - None exists.
7.
References -
Lawless, E. W., R. von RUmker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-OO-72-04, June 1972.
von Rumker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-311, Final Report, 15 March 1974.
87
-------
NITRATED HYDROCARBON PESTICIDES
PROCESS NO. 27
Benefin Process
1.
Function - Benefin, a solid dinitroaniline, is produced by reaction
of chloro-4-trifluoromethylbenzene, HN03/H2S04 and butylethylamine.
The nitration process is the same as for trifluralin. Since bene fin
and trifluralin are both made by Eli Lilly and Company. the nitrated
product (chloro-4-trifluoromethyl-2,6-dinitrobenzene) is probably
fed to both processes. Also, both final processes may use the same
equipment by switching from dipropylamine to butylethylamine.
Z.
Input Materials - Chloro-4-trifluoromethylbenzene, HN03/HZS04 and
butylethylamine.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - The wastewaters contain NaCl.
6.
EPA Source Classification Code - None exists.
7.
References -
Lawless, E. W., R. von Rurnker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture,' Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-OO-7Z-04, June 1972.
..
von Rurnker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-3ll, Final Report, 15 March 1974.
88
-------
Other Nitrogenous Pesticides
This group of pesticides includes all pesticides containing nitrogen which
have not been covered in the previous carbamate, triazine, anilide, urea,
and nitrated hydrocarbon industrial segments. This group includes deriva-
tives of imines, amines, cyanides, hydrazines, and guanidines. Fifteen
pesticides with production exceeding 1 million pounds in 1972 are included
in this group.
The estimated production in 1972 of other nitrogenous pesticides was 52
million pounds. The imide fungicides were the most popular with cap tan
at 17 million pounds. CDAA, a preemergence herbicide, was next at 6 mil-
lion pounds. Maleic hydrazide, a growth retardant, accounted for 4.5
million pounds.
The -chemical reactions and structures of many of these nitrogenous pest-
icides are presented in Figure 23. The imide pesticides (captafol, captan
and folpet) have a similar reaction of a sulphenyl chloride with an imide
and NaOH. Many other nitrogenous pesticides also have a similar reaction
between a chloride and an amine or other nitrogenous compound (as shown
in Figure 23). No information is available for the reactions to produce
methomyl and benomyl, which are both classified as amate pesticides.
The flow sheet for the imide and other nitrogenous pesticide processes
is shown in Figures 24 and 25. The first two groups of imides and other
pesticides have similar reaction processes with the inputs for each pest-
icide in line across the flow sheet.
Data for several of the processes within this industry
available. These processes for which detailed process
not prepared in~lude:
segment were not
descriptions were
Cl Addition Process
Nitralin Process
Pichloram Process
Diphenamid Process
Dedine Process
Naphthalam Process
Methomyl Process
Benomyl Process
89
-------
~ . C . N(CH)2 =-J + N.CI + H20
@'O
Dipn.l"'Cmid
~H3 9 ~
CH3 - I - C = N - 0 - C - N - CH)
Methomyl
I CHLORIDE I NITROGEN NIUOGENIOUS
~O~ COMPOuND lliT~lQ.E-
~H 0
NoOH + CHCI2CCl2SC1 ' ~ - ICCI)CHCI2
I 0
I ~.fol
/
I ~_ICCI)
/
NoOH + CCI)ICI --------+
I ' I
"
<:,:p,ton
"
, ~H 0
"
~.ICCI)
' .
0 Fol~t
o 0
"
CHzClC . CI I . HN(CH2CH - CH2h I CH,CIC . N(CH2CH = CH2),
CDM
!@L CH)
I + HN(C2Hsn @1.N(C2HSn
I
DH'
C~H9OCH2CH2OCH::>CH)CI ... NaSCN C~H9
-------
~
(SuI phenyl
Chloride
Compound
~
Imide Pesticide
Process
28 29
Imide Compound.9.../
1, 1.2,2- T etrach laroethylsu/phenyl Chloride _[T etrahydrophtha limide
T ri chloromethylsulpheny I Chloride~ T etrahydrophtha limide
" Phthalimide
Chloroocetyl Chloride
M-toluyl Chloride
Butyl "Carbitol" Chlori de
Ethyl Chlorocarbamate
CI Addition
Process
Nitrogen Compound
[ Diallyomine
Diethylamine
Sodium Thiocyanate
N-methy Idth i ocarbcmate
!U
[CaPtafO!
Captan
Folpet
[ CDAA
Deet
Lethane 384 @
Methyl Isothiocyanate
.:=.J Input materials are in line with the respective pesticide product.
Nitralin
Process
Pichloram
Process
1. H2S04
2. NH3
Diphenamid
Process
Figure 24. Flow sheet for imides and
other nitrogenous pesticide processes
91
-------
?
?
Figure 25.
Dodine
Process
Maleic Hydrazide
Process
Noptha/am
Process
Methomyl
Process
.1
Benomyl
Process
Flow sheet for other nitrogenous
pesticide processes
92
-8
-------
OTHER NITROGENOUS PESTICIDES
PROCESS NO. 28
Imide Pesticide Process, Cap tan
1.
Function - Captan is produced by the reaction of sodium hydroxide,
trichloromethylsulphenyl chloride (perchloromethyl mercaptan (PMM)),
and tetrahydrophthalimide (THPI). Both PMM and THPI are manufac-
tured on site.
Captan is produced in a two-step reaction process followed by
several purification steps. The first reaction step is simply the
dissolving of P~l in NaOH to form the sodium salt of PMM and water.
The second reaction step combines this salt and THPI to form captan
and NaCl. The captan is then purified and packaged.
2.
Input ~Bterials - Sodium hydroxide, trichloromethylsulphenyl chlor-
ide, and tetrahydrophthalimide.
3.
Operating Parameters - Second reaction step:
- Temperature: 10 to 30°C.
- Pressure: Atmospheric.
- Reaction time: 10 to 40 min.
- Solution: Aqueous medium of pH 10.0 to 10.5.
4.
Utilities - Data not available.
5.
Waste Streams -
Process Wastes and Losses at One Plant
Material
Amount produced
(lb/lb AI)
Disposition
Form
Active ingredient
Solvents
Liquid
Particulates
,... 4 lb/day
10 tons/year
Asphalt-lined sett-
ling pond; discharge
Local collector
Local scrap dealers
Buried on plant
property
Solid paper
Metal
Miscellaneous
chemicals
10 tons/year
25 tons/year
1,200 lb/year
6.
EPA Source Classification Code - None exists,
93
-------
7.
References -
Lawless, E. W., R. von Rumker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-OO-72-04, June 1972.
von Rumker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-3ll, Final Report, 15 March 1974.
Sittig, M., Pesticide Production Processes 1967, Noyes Development
Corporation (1967).
California Spray-Chemical Corporation, The Chemistry of Captan, 31
March 1955.
94
-------
OTHER NITROGENOUS PESTICIDES
PROCESS NO. 29
Imide Pesticide Process, Folpet
1.
Function - Folpet is made by reaction of sodium hydroxide, trichloro-
methylsulphenyl chloride, and phthalimide. Folpet is made by Calhio
Corporation at Perry, Ohio, in the same facility which produces cap-
tan and with the same trichloromethylsulphenyl chloride (perchloro-
methyl mercaptan) intermediate chemical.
The steps for producing the trichloromethylsulphenyl chloride are
the same as in the production of captan. The phthalimide is produced
by an amination reaction similar to that used in captan production.
2.
Input Materials - Sodium hydroxide, trichloromethylsulphenyl chlor-
ide and phthalimide.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - Similar to captan (see preceding process sheet).
6.
EPA Source Classification Code - None exists.
7.
References -
Lawless, E. W., R. von Rurnker, and T. L. Ferguson, The Pollution
Potential in Pesticide Manufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-OO-72-04, June 1972.
von Rumker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-311, Final Report, 15 March 1974.
Sittig, M., Pesticide Production Processes 1967, Noyes Development
Corporation (1967).
95
-------
OTHER NITROGENOUS PESTICIDES
PROCESS NO. 30
Maleic Hydrazide Process
1.
Function - Maleic anhydride and dihydrazine sulfate are combined
to yield maleic hydrazide, a solid hydrazide pesticide.
2.
Input Materials - Maleic anhydride and dihydrazine sulfate.
3.
Operating Parameters - Temperature:
75 to 110°C (exothermic re-
action) .
- Reaction time: About 3-1/2 hr with stirring
- Product recovery: Batch cooled to 25°C.
Product recovered by
vacuum filtration, then
washed free of sulfate
and dried.
4.
Utilities - Data not available.
5.
Waste Streams - H2S04 is a by-product.
6.
EPA Source Classification Code - None exists.
7.
Reference -
Sittig, M., Pesticide Production Processes 1967, Noyes Development
Corporation (1967).
96
-------
Organoarsenic and Organometallic Pesticides
The organoarsenical and organometallic pesticides are a small group of
abo~t 15 pesticides. The organoarsenical pesticides are herbicides, and
the ~rganometallic pesticides are predominantly mercury and copper fungi-
cides.
The organoarsenic pesticides are all derived from sodium arsenite. DSMA,
the derivative, is also the intermediate chemical for producing Y~MA,
methane arsenic acid and cacodylic acid as indicated in Figure 26. The
structure of the organoarsenic pesticides is:
Rl
CR3AS~
R2
Pesticide
Rl
~
DSMA
MSMA
MAA
Cacodylic
acid
-ONa
-ONa
-OR
-CR3
-ONa
-OR
-OR
-OR
The main two organomercuric pesticides are formed with benzene from mer-
curic acetate and mercuric oleate to form PMA and phenyl mercuric oleate.
The major organocopper pesticide is formed by reacting naphthenic acids
with soluble copper salts to form copper naphthenates.
The estimated' production in 1972 of organoarsenic pesticides was 32.7
million pounds. MSMA and MAA accounted for 24 million pounds of the
total. The combined organomercuric production was less than 1 million
pounds. The copper naphthenates were the leading organometallic pesti-
cide at 2.2 million pounds. Based on the Tariff Commission data, the
production of organoarsenic pesticides increased from 32.7 to 42.1 mil-
lion pounds from 1972 to 1973. The production has~ncreased signifi-
cantly for each year from 1971 through 1973.
The chemical reactions for all of these pesticides are
Figure 26. Also, the flow sheet for organoarsenic and
pesticide processes is shown in Figure 27.
indicated in
organometallic
97
-------
Arsenicals:
1/2 AS203
I.D
00
Mercuric:
@
3NaOH
~ Na3As03 + 3/2 H20
~~
'-"0-
""
CH AsO(ONa)2 H2S04 CH3AsO(ONa)OH + NaS04
3DSMA 2 . MSMA
rJ=! 0 ~
o N CH3AsO(OH)2 + NaS04
Methane Arsenic Acid
CH3AsO
1N
:r: Z
N a
o 0
:r: CH3CI
CH3As(ONa)2 0'" (CH3>2AsO(ONa)
H2
HCI
. (CH3)2AsO(OH) + NaCI
Cacadd!.£ + Na2S04
Acid
9
Hg(OC -CH3>2
1-I9(0!? ,
C~C
71-1 14~C1-l
~1-I~C
81-117)2
o
~ 'I
~ ~Hg-O-C-CH3
PMA
o
~ "
~ Hg-O-C-C7H14-CH=CH-CSH17
Phenyl Mercuric Oleate
Cop~er Na~hthenates:
Naphthenic Acids + Soluble Copper Salts ~Copper Naphthenates
Figure 26.
Chemical reactions to produce organoarsenic
and organometallic pesticides
-------
DSMA
Process
3
@
Acid
MSMA
Process 32
Methane Arsenic
Acid Process
Cacodylic Acid
Process
33
PMA Process
Phenyl Mercuric
Oleate Process
Copper
Naphthenate
Process
Figure 27. Flow sheet for organoarsenic and
organo~etallic pesticide processes
99
-------
Data for some of the processes in this industry segment were not avail-
able. These processes for which detailed descriptions were not prepared
include:
Methyl Arsenic Acid Process
PMA Process
Phenyl Mercuric Oleate Process
Copper Naphthenate Process
100
-------
ORGANOARSENIC AND ORGANOHETALLIC PESTICIDES
PROCESS NO. 31
DSMA Process
1.
Function - DS~~ is produced by the reaction of arsenic trioxide,
sodium hydroxide, and methyl chloride. The process includes a
two-stage reaction, precipitation and filtration. The reaction
chemistry is as follows:
ASZ03 + 6NaOH
> ZNa3As03 + 3~O
(1)
Na3As03 + CH3Cl
)
(2)
CH3AsO(ONa)2 + NaCl
( DSMA)
In practice, the reaction in Eq. (1) is not initially allowed to go
to completion. A sodium to arsenic ratio of less than 3:1 is used
initially with the balance of the NaOH being added in proportion to
the addition of methyl chloride. An excess of CE3Cl is used in
order to assure a virtually complete conversion of the sodium ar-
senite.
Following the addition of all reactants, the contents are allowed
to "digest" until the reaction ceases. The contents are then cooled
and the DSMA is precipitated by the addition of a suitable liquid
such as isopropyl alcohol.
2.
Input Materials - Arsenic trioxide, sodium hydroxide, and methyl
chloride.
3.
Operating Parameters - Reaction
Reaction
- Pressure
(2) temperature: 60 to 90°C.
(2) pressure: 60 to 120 psig.
after "digestion": 5 to 10 psig.
4.
Utilities - Data not available.
5.
Waste Streams - NaCl appears as a waste product of the methyl-
arsenic unit but no data are available as to the disposition of
the waste.
6.
EPA Source Classification Code - None exists.
101
-------
7.
Reference -
..
von Rumker, R., E. W. Lawless, and A. F. ~~iners, Production, UseL
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-311, Final Report, 15 March 1974.
102
-------
ORGANOARSENIC AND ORGANO~lliTALLIC PESTICIDES
PROCESS NO. 32
MS~~ Process
1.
Function - ~ISMA is produced by the reaction of DSMA and sulfuric
acid. To obtain MSMA, crude DSMA is combined in a single-stage re-
action with H2S04' The products are then passed through an evapora-
tion step where aqueous CH30H is removed. The remaining product is
then centrifuged to obtain 58% MSMA and by-product salts.
2.
Input Materials - DSMA and sulfuric acid.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - Discharge at one plant to two equalization ponds
contains 0.7 to 0.8 ppm arsenic as well as NaCl and Na2S04. The
by-product salts, Na2S04 and NaCl, are a disposal problem because
they contai.n arsenic. One manufacturer washes the salts in a five-
stage countercurrent washing cycle and then disposes of them in an
approved dump.
6.
EPA Source Classification Code - None exists.
7.
Reference -
von Rumker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-3l1, Final Report, 15 March 1974.
103
-------
ORGANOARSENIC AND ORGA~D~lliTALLIC PESTICIDES
PROCESS NO. 33
Cacodylic Acid Process
1.
- Cacodylic acid, a solid organoarsenic pesticide, is
reaction of DS~~ (or the equivalent input materials),
and methyl chloride.
Function
duced by
dioxide,
pro-
sulfur
2.
Input Materials - DS~, sulfur dioxide, and methyl chloride.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - At one plant all the liquid streams are recycled for
reuse. A number of multiple effect evaporators are employed in the
solution recycling systems. The process does, however, create a
solid waste which is a mixture of sodium chloride and sodium sulfate
containing 1 to 1-1/2% cacodylate contaminants.
6.
EPA Source Classification Code - None exists.
7.
References -
Ottinger, R. S., J. L. Blumenthal, D. F. Dal Porto, G. I. Gruber,
M. J. Santy, and C. C. Shih, TRW Systems Group, Recommended Methods
of Reduction, Neutralization, Recovery of Disposal of Hazardous
Waste, Volume VI, U.S. Environmental Protection Agency, Contract
No. 68-03-0089. Washington, D.C., August 1973.
von R~mker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-3ll, Final Report, 15 March 1974.
104
-------
Microbial and Natural-Occurring Pesticides
Two types of microorganisms pathogenic to insects have been
are in limited commercial use on several crops today, i.e.,
of Bacillus species, and nuclear polyhedrosis viruses.
developed and
preparations
Several commercial products based upon Bacillus thurin~iensis are cur-
rently available on the U.S. market. These products are exempted from
the requirement of a tolerance and are registered for the control of
lepidopterous insects on a considerable number of crops. The main de-
terrent to their use is that growers are familiar with the chemical in-
secticides and their more rapid mode of action, and chemical insecticides
are often less expensive per unit control. Preparations based on Bacillus
popilliae and several other Bacillus species are under commercial develop
ment, but have not yet reached the volume of use of Bacillus thuringien-
sis.
Several nuclear polyhedrosis virus preparations are available in the U.S.
for control of cotton bollworms, Heliothis spp. These products are not
widely used at this time. Problems concerning their large-scale produc-
tion, formulation, storage stability, application timing and methods,
stability after application, and safety precautions remain to be resolved.
Development work is in process on a number of other insect viruses, in-
cluding those of the cabbage looper, Trichoplusia ni; the alfalfa looper,
Autographa californica; the Douglas fir tussock moth, Hemerocampa pseudo-
tsugata; and several others.
Bacillus preparations are of interest to growers, especially for the con-
trol of lepidopterous insects on lettuce and cole crops clos~ to harvest
when there may be restrictions on the use of chemical insecticides. 80
far as application timing and technique is concerned, Bacillus prepara-
tions can be used as direct substitutes for chemical insecticides for the
uses for which they are registered, or even combined with chemicals in
the spray tank. On the other hand, the virus preparations known to date
do not work well if they are used in the same manner as chemical insecti-
cides. They normally work best as components of complete integrated pest
management systems.
Microbial pathogens useful for the nonchemical control of weeds or plant
diseases have not been commercially developed to this date.
Natural-occurring pesticides include the pyrethrins and obtusaquinone.
The pyrethrins are derived from the chrysanthemum flower, and obtusa-
quinone is an orange pignlent of the tropical cocobolo tree. Pyrethrin
pesticides have also been synthesized and some of these offer promise
as insect-specific insecticides.
105
-------
The processes for production of the microbial and natural-occurring pes-
ticides are at present considerably different from the chemical reactions
for other pesticides. The microbial pesticides are developed from cul-
tures in fermented solutions as expressed by the following procedure for
Bacillus thuringiensis:
Nutrient
mixture
Sterilize> Innoculat~ Ferrnen~ Separat~
Product solid
~ containing
- 3% B.t.
The pyrethrins are extracted from chrysanthemum flowers as follows:
Chrysanthemum
flowers
(Pyrethrum
cineraefolium)
>
C6H14
Pyrethrin
concen-
)
trate
Crude
solven~ Extract
Extract with
CH30H
Extract with
The most popular microbial pesticide is Bacillus thuringiensis with an
estimated production of 1 million pounds in 1972. The total production
of microbial and natural-occurring pesticides was about 2 million pounds
in 1972. The use of these pesticides is expected to increase signifi-
cantly in the next decade as new and more effective derivatives are
formed and as some of the more toxic and persistant chemical pesticides
are forced out by environmental restrictions.
The input materials for
cesses are indicated in
the process description
Bacillus thuringiensis
Figure 28. Additional
sheets.
and pyrethrin and the pro-
details are presented in
The reaction and production processes for Bacillus thuringiensis and the
pyrethrins -are described in the following process description sheets
(Processes 34 and 35). Other microbial and natural-occurring pesticide
processes are not included since production volumes are low and the pro-
cess data are not available.
106
-------
Baci /Ius
thud ngiensis
Process' 34
I-'
o
-....J
Recover
Pyrethrin Process,
Methanol Extract
35
Pyrethrin Process,
Hexane Extract
35
Recover
Figure 28. Flow sheet for microbial and
natural-occurring pesticide processes
thud ngiensis
""---/
-------
MICROBIAL AND NATURAL-OCCURRING PESTICIDES
PROCESS NO. 34
Bacillus thuringiensis Process
1.
Function - Bacillus thuringiensis (B.t.) is produced via a fermen-
tation process. The input materials identified below are added to
a fermentation tank containing water and innoculant B.t. After
fermentation the material containing B.t. is withdrawn and centri-
fuged to separate the solids. These solids are then dried and
milled to obtain a solid containing 3% B.t.
2.
Input Materials - Soybean meal, corn steep liquor, minerals,
and innoculant B.t. (alternate process: wheat bran, casein,
lasses, vitamins, water and innoculant B.t.).
water,
mo-
3.
Operating Parameters - D~ta not available.
4.
Utilities - Data not available.
5.
Waste Streams - The liquid wastes from the fermentation tank are
either passed to an evaporation pond or are sterilized with heat,
treated and discharged to a lake.
6.
EPA Source Classification Code - None exists.
7.
Reference -
Lawless, E. W., T. L. Ferguson, and R. von Rurnker, Pollution Po-
tential in Pesticide Manufacture, Final Report, by Midwest Research
Institute on Contract No. 68-01-0142 for the Environmental Protec-
tion Agency, June 1972.
108
-------
MICROBIAL AND NATURAL-OCCURRING PESTICIDES
PROCESS NO. 35
pyrethrin Process
1.
Function - The pyrethrins, derivatives of the chrysanthemum flower,
are produced by an extraction process using methanol and hexane.
The process incorporates two extraction steps, a dewaxing extraction
and a deresining extraction.
First, the methanol and crude pyrethrin are mixed. The wax residue
is recovered as a by-product. The methanol extract is filtered with
charcoal and then stripped and distilled. The distillation yields
methanol and semi-finished pyrethrin. The methanol is recycled to
the process and the pyrethrin is combined with the hexane. The resin
from this step is recovered as a product. The hexane extract is fil-
tered with iono1 and ce1ite and then stripped. The stripping yields
hexane which is recycled and pyrethrin concentrate. The concentrate
is then diluted in kerosene to obtain 20% pyrethrin.
2.
Input Materials - Crude pyrethrin and rn2ke-up amounts of methanol
and hexane.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - Data not available.
6.
EPA Source Classification Code - None exists.
7.
Reference -
Lawless, E. W., T. L. Ferguson, and R. von RUmker, Pollution Po-
tential in Pesticide Manufacturing, Final Report, by Midwest Re-
search Institute on Contract No. 68-01-0142 for the Environmental
Protection Agency, June 1972.
109
-------
Other Pesticides
Organic pesticides which did not fit well in other operations include
methyl bromide, endothall, bensulide and EXD. These four pesticides are
discussed in this industry segment. Some other organic pesticides may
have been omitted because of low volumes of production (100,000 lb/year
or less). Other large-volume pesticides such as elemental sulfur, sodium
chlorate, and the organotin compounds were excluded because these mate-
rials are products of other industries and are predominantly used for
other purposes. Creosote has also been excluded since it is a natural
product from coking operations at foundries. (Note that creosote is the
number one pesticide with about 1 billion pounds used in 1972 as a wood
preservative for fence posts, railroad ties and telephone poles.)
Methyl bromide is the most popular of these "other" pesticides with an
estimated production in 1972 of 25 million pounds. The other pesticides
also include endothall at 2 million pounds, bensulide at 1 million pounds
and EXD at 0.5 million pounds.
The chemical reactions and structures of the four pesticides (methyl
bromide, endothall, bensulide and EXD) are presented in Figure 29. As
can be seen, none of the reactions or structures arc similar. The pro-
cess flow sheet is presented in Figure 30.
Data for some of the processes in this industry segment were not avail-
able. These processes for which detailed process descriptions were not
prepared include:
Bensulide Process
EXD Process
no
-------
1. Meth)'1 Bromide:
6CH30H + 3Br2 + S-.6CH3Br + H2S04 + 2H20
Meth)" Bromide
2. Endotha II :
° 0 0
O 01 /; (W" Reduction $C-OH
0+ 0--. 0 .. 0
- r-OH
~ ~ ~
o ~O 0
~..y 0 Endothall
(£to C -ONa
C-ONa
II
o
Endotho/l - Na
3. Bensulide:
I-'
I-'
I-'
@-9 ~ _OCH(CH3)2 @-9 ~ /OCH(CH3)2
l-NH-CH2-CH2-CI + No-S-P -OCH(CH3)2 ~ 0 gNH-CH2-CH2-S-P ",OCH(CH3)2 + NaCi
4. EXD:
Bensulide
NoOH ?
C2HsOH + C52 .. C2HsOC-5-Na + H20
50diumethylxanthote
, Oxidized(HCI?)
5 5
II t'
C2HSO-C-S-5-C-OC2Hs + (NoCI?)
EXD
Figure 29.
Other pesticides chemical reactions and structures
-------
Methyl Bromide
Process 36
37
N-(,B-chloroethyl)
Benzene
Sulfonamide
Sodium "---/
( Diisopropyl
Dithiophosphate
'--/
Bensulide
Process
EXD Process
Figure 30.
Flow sheet for other pesticide processes
112
-------
OTHER PESTICIDES
PROCESS NO. 36
Methyl Bromide Process
1.
Function - Methyl bromide is prepared by a simple bromination pro-
cess using methanol, elemental bromine, and sulfur. The input
materials are reacted in a fractionation system to form methyl
bromide (CH3Br) and sulfuric acid. The CH3Br is dried with silica
gel and packaged.
2.
Input Materials - Methanol, bromine, and sulfur.
3.
Operating Parameters - Data not available.
4.
Utilities - Data not available.
5.
Waste Streams - The H2S04 is recovered. The fumes are
NaOH, treated and discharged. The wastewater from the
cess may possibly contain Na2S04'
scrubbed with
scrubbing pro-
6.
EPA Source Classification Code - None exists.
7.
Reference -
von Rumker, R., E. W. Lawless, and A. F. Meiners, Production, Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute fo~ Council on Environmental Quality, Contract
EQC-3ll, Final Report, 15 March 1974.
113
-------
OTHER PESTICIDES
PROCESS NO. 37
Endothall Process
1.
Function - Endothall is produced by a Diels-Alder condensation re-
action of furan and maleic anhydride followed by a reduction reac-
tion or a NaOH addition reaction. The NaOH reaction yields the
endothall--Na salt.
2.
Input Materials - Furan and maleic anhydride plus a reducing agent
(HCl) or NaOH to form the Na salt.
3.
Operating Par~~eters - Temperature:
This reaction is conducted at
a temperature of about 35°C.
- Pressure: The furan-malcic anhydride conden-
sation is carried out at atmo-
spheric pressure.
- Reaction time: A reaction time of about 7 hr
is sufficient for the con-
densation of furan and
maleic anhydride at a tem-
perature of 35°C.
- Reaction medium: This reaction is carried
out in the liquid phase.
Isopropyl ether may be
used as a reaction diluent
4.
Utilities - Data not available.
5.
Waste Streams - Data not available.
6.
EPA Source Classification Code - None exists.
7.
Reference -
Sittig, M., Pesticide Production Processes 1967, Noyes Development
Corporation (NDC), Chemical Process Review No.5 (1967).
114
-------
APPENDIX A
LISTS OF PROCESS INPUT MATERIALS FOR THE
PESTICIDES INDUSTRY
115
-------
Table A-l.
CHLORINATED HYDROCARBON PESTICIDES
Pesticide
Toxaphene
Strobane
Bandane
Ethylene dichloride
Hexachloracetone
Chloroacetic acid
TCA
Dalapon
PCNB
Dacthal (DCPA)
Dicarnba
Z,3,6-TBA
Chloramben
Methoxychlor
DDD
DDT
2,4,5-Trichlorophenol
PCP
2,4-D
2,4-DB
Dichlorobenzene
Hexachlorophene
2,4,5-T
Silvex
Hexachlorobenzene
Benzene hexachloride
MCPA
MCPB
Bromoxynil~/
Dichloropropene
2-./
Input materials
Chlorine, a-pinene
Chlorine, mixed terpenes
Chlorine, bicyclopentadiene
Chlorine, ethylene
Chlorine, acetone
Chlorine, acetic acid
Chlorine, acetic acid (3 moles)
Chlorine, propionic acid
Chlorine, nitrobenzene
Chlorine, C6H4 (COCl)2' CH30Na
Chlorine, benzene methanol, C02' (CBj)2S04
Chlorine, toluene, oxygen
Chlorine, benzoic acid, ammonia
Chlorine, ethanol, anisole
Chlorine, ethanol, chlorobenzene
Chlorine, ethanol, chlorobenzene
Phenol, chlorine
Phe.,;)l, chlorine
2,4-Dichlorophenol,
2,4-Dichlorophenol,
Chlorine, benzene
2,4,5-Trichlorophenol, CHZO
2,4,5-Trichlorophenol, NaOH,
2,4,~-Trichlorophenol, NaOH,
Chlorine, benzene, catalyst
Chlorine, benzene, UV light source
4-Chloro-£-cresol, sodium monochloroacetate
4-Chloro-£-cresol, butyrolactone
4-Hydroxybenzaldehyde, bromine, (NHZOH)
l,3-Dichloro-Z-propanol, POCl3
ClCH2COOH, NaOH
butyrolactone
ClCHZCOOH
Cl (CHZ)ZCOOH
Bromoxynil is classified as a phenoxie but is brominated instead of
chlorinated.
116
-------
Table A-2.
DIENE-BASED PESTICIDES
Pesticide
Input materials (1 mole/mole base)
Aldrin
Hexachlorocyclopentadiene; bicyclo-(Z.Z.l)-Z,5
heptadiene
Dieldrin
Aldrin; H20z; acetic acid
Chlordane
Hexachlorocyclopentadiene; cyclopentadiene; ClZ
Heptachlor
Hexachlorocyclopentadiene; cyclopentadiene; AlCl3
or SOZClZ + benzoyl peroxide in benzene
Isodrin
Hexachlorocyclopentadiene; vinyl chloride (or
acetylene); cyclopentadiene
Endrin
Isodrin (or ingredients); HZOZ; acetic acid
Endosulfan
Hexachlorocyclopentadiene; cis-Z-butane-l,4-diol;
thionyl chloride
Isobenzan (telodrin)
Hexachlorocyclopentadiene (Z moles); Z,5-dihydro-
fur an; ClZ
Alodan
Hexachlorocyclopentadiene; ~H-CHZCl
CH-CH2Cl
Bromodan
Hexachlorocyclopentadiene; CHZ = CHCHZBr
Kepone
Hexachlorocyclopentadiene; S03; HZO
Mirex
Hexachlorocyclopentadiene; AlCl3
Pentac
Hexachlorocyclopentadiene; HZ or Cu
117
-------
Table A-3.
ORGANOPHOSPHATE PESTICIDES
Pesticide
Input materials
Acyclic:
Trichlorfon
£-£-Di-~-propyl phosphorochloridothioate, water,
pyridine and sodium carbonate
Butyl mercaptan and phosphorus oxychloride
£-£-Diethyl phosphorochloridothioate and
2-hydroxethyl ethyl sulfide
Trimethyl phosphite and chloral (Alternate:
triclorfon)
Trimethyl phosphite and N,N-dimethyl methyl-2-
chloroacetoacetamide
Sodium dimethylphosphorodithioate and N-methyl-
a-chloroacetamid~
Sodium diethylphosphorodithioate and f3-chloro-
ethyl thioethyl ether
£-£-Diethyl phosphorodithioic acid and dibromo-
methane
£-£-Dimethyl phosphorodithioic acid and diethyl
maleate
Butyl mercaptan and phosphorus trichloride
(alternate: dibutyldisulfide and phosphorus)
Trimethyl phosphate and methyl-2-chloroaceto-
acetate
£-£-Dimethylphosphoroamidothioate
Trimethyl phosphite and N-methyl methyl-2-chloro-
acetoacetamine
Dichlorvos and bromine
Dimethyl phosphorochloridothioate and 2-hydroxy-
ethyl ethyl sulfide
£-£-Diethyl phosphorodithioic acid, formaldehyde
and ethyl mercaptan
Diethyl phosphorochloridothioate and water (with
pyridine and sodium carbanate)
Trimethyl phosphite, sulfurylchloride and
acetoacetic acid diethylamide
Dimethyl phosphite and chloral
Aspon
DEF
Demeton
Dichlorvos
Dicrotophos
Dimethoate
Disulfoton
Ethion
Malathion
Merphos
Mevinphos
Monitor
Monocrotophos
Naled
Methyl demeton
(oxydemeton)
Phorate
TEPP
Phosphamidon
118
-------
Table A-3.
(Concluded)
Pesticide
Cyclic:
Abate
Azinphos-methyl
Carbophenothion
Dursban (clopyrifos)
Crotoxyphos
Coumaphos
Crufomate
Diazinon
Dioxathion
Dyfonate (fonophos)
Dasanit (fensulfothion)
Fenthion
Methyl parathion
Parathion
Phosmet (Imidan)
Fenchlorophos (Ronnel)
Dicupthon
Famophos
Input materials
Dimethyl phosphorochloridothionate and bis-
(P-hydroxyphenyl) sulfide
£-£-Dimethyl phosphorodithioic acid and
N-chloromethylbenzazimide
£-E-Diethyl phosphorodithioic acid and
N-chloromethylbenzazimide
Sodium diethylphosphorodithioate and 4-chloro-
phenyl chloromethyl sulfide
Diethyl phosphorochloridothioate and 3,5,6-
trichloro-2-pyridinol
Diethyl phosphorochloridothionate and 3-chloro-
4-methyl-7-hydroxycownarin
4-!-Butyl-2-chlorophenol, phosphonyl chloride,
methanol, methylamine
Diethyl phoshporochloridothionate and 2-isopropyl-
4-methyl-6-hydroxyprimidine
E-E-Diethyl phosphorodithioic acid and 2,3-
dichloro-£-dioxLne
No data
Diethyl phosphorochloridothioate and 4-methyl-
thio-l-hydroxybenzene
Dimethyl phosphorochloridothionate and 4-methyl- -
thio-m-cresol
Dimethyl phosphorochloridothioate and sodium
4-nitrophenate
Diethyl phosphorochloridothioate and sodium
4-nitrophenate
Sodium dimethylphosphorodithioate phthalimide,
formaldehyde and chlorine
2,4,5-Trichlorophenyl phosphorochloridothioate
sodium and methanol
Dimethyl phosphorochloridothionate and sodium
2-chloro-4-nitrophenate
2-£-Dimethyl phosphorochloridothioate, N,N-
dimethyl-l-phenol-sulfonomide, sodium hy-
droxide and water
119
-------
Table A-4.
CARBAMATE PESTICIDES
Pesticide
Input materials
Carbamates and thio-:
Aldicarb
Barban
Butylate
Carbaryl
Carbofuran
Chloroprophan
Cycloate
Di-allate
EPTC
Molinate
Pebulate
Propham
Trl-allate
Verno late
Dithiocarbamates:
CDEC
Dimethyldithiocarbamic
acid, K salt
Dimethyldithiocarbamic
acid, Mn salt
Ethylene-bis(dithio-
carbamic acid), di-
ammonium salt ferban
Ferban
Me tham
Nabam
Maneb
Zineb
Dimethylethylene, sodium nitrate, Hel, methyl-
thiosodium and methylisocyanate
4-Chloro-2-butynol and 3-chlorophenylisocyanate
(Alternate: 4-chloro-2-butynol, 3-chloro-
aniline)
Diisobutylamine, phosgene and ethyl mercaptan
l-Napthyl-chloroformate, methylamine and sodium
hydroxide
2,3-Dihydro-2,2-dimethyl-7-benzofuranol and methyl
isocyanate
~-Chloroaniline and isopropyl chloroformate
N-ethylcyclohexylamine and ethylchlorothio-
formate
Diisopropylamine, phosgene and 2,3-dichloro-
propenyl-I-thiol
Di-E-propylamine, phosgene and ethyl mercaptan
(Alternate: di-~-propylamine and ethylchloro-
thioformate)
Hexamethyleneimine and ethylchlorothioformate
Ethyl-E-butylamine, phosgene and n-propyl mer-
captan (Alternate: ethyl-E-butylamine and n-
propylchlJrothioformate)
Aniline and isopropyl chloroformate
Diisopropylamine, phosgene and 2,3,3-trichloro-
phenyl-I-thiol
Di-E-propylamine, phosgene and n-propyl mer-
captan
Diethylamine, carbon disulfide, sodium hydroxide
and 2,3-dichloropropene
Dimethylamine, carbon disulfide and potassium
hydroxide
K salt (above) or Na salt and manganese sulfate
(or chloride)
Ethylenediamine, carbon disulfide and ammonia
Dimethylamine, carbon disulfide, sodium hydroxide
and iron salt (chloride or sulfate)
Methylamine, carbon disulfide and sodium hy-
droxide
Ethylenediamine, carbon disulfide and sodium
hydroxide
Nabam and manganese salt (chloride or sulfate)
Nabam and zinc salt (chloride or sulfate)
120
-------
Table A-S.
TRIAZINE PESTICIDES
Pesticide
Input materials (1 mole/mole base)
Arnetryne@
Atrazine, methyl mercaptan
Atrazone
Atrazine, methyl alcohol
Atrazine
Cyanuric chloride, ethylamine, (CH3)CHNHZ
Blade~
Ethylamine, cyanuric chloride (CH3)2C(CN)NH2
Chlorazine
Cyanuric chloride, (C2HS)2NH, CIC6H4NH2
Cyprazine
Cyanuric chloride, CH2CH2CHNH
Dyrene@
Ortho-Chloroaniline, cyanuric chloride
Igran saWID (Terbutryne)
Cyanuric chloride, ethylamine, (CH3)3CNH2, methyl
mercaptan
MPMT
Cyanuric chloride, CH30(CH2)3NH2 (2 moles)
Prometone
Propazi~e, methyl mercaptan
Simazine
Propazin~, methyl alcohol
Cyanuric chloride, (CH3)2CHNH (2 moles)
Cyanuric chloride, ethylamine (2 moles)
Cyanuric chloride, ethylamine (2 moles)
Prometryne
Propazine
Trietazine
121
-------
Table A-6.
ANILIDE PESTICIDES
Pesticide
Input materials
Alachlor
Butachlor
Propachlor
Propanil
Diethylaniline, paraforrnaldehyde, chloroacetyl chloride,
anhydrous ammonia, methanol
Diethylaniline, paraforrnaldehyde, chloroacetyl chloride,
anhydrous ammonia, butanol
Aniline, paraformaldehyde, chloroacetyl chloride, anhy-
drous ammonia, isopropanol
3,4-Dichloroaniline, propionic acid, thionyl chloride
122
-------
Table A-7.
UREA AND URACIL PESTICIDES
Pesticide substituted
ureas
Diuron
Linuron
Fluometuron
Siduron
Chloroxuron
Monuron
Monuron-TCA
Uracils
Bromacil
Terbacil
Input materials
3,4-Dichloroaniline,
amine (Alternate:
and dimethylamine)
phosgene and dimethyl-
3,4-dichloroaniline, urea
3,4-Dichloroaniline, phosgene and C,N-dimethyl
hydroxylamine
3-Trifluoromethyl aniline, phosgene and di-
methylamine
Aniline, phosgene and 2-methylcyclohexylamine
4-(4-Chlorophenoxy) aniline, phosgene and di-
methylamine
E-Chloroaniline, phosgene and dimethylamine
(Alternate: p-chloroaniline, urea and di-
methylambe)
Monuron and' trichloroacetic acid
~-Butylamine, phosgene, ammonia, ethylaceto-
acetate and bromine
~-Butylamine, phosgene, ammonia, ethylaceto-
acetate and chlorine
123
-------
Table A-8.
NITRATED HYDROCARBON PESTICIDES
Pesticide
Input materials
Trifluralin
HN03/H2S04' chloro-4-trifluoromethylbenzene and di-
propylamine
Benefin
HN03/H2S04' chloro-4-trifluoromethylbenzene and
butylethylamine
Dinoseb
HN03/HzS04' £-~-butylphenol
DNOC
£-Cresol, HzS04 and HN03/HzS04
Nitrofen
2,4-Dichlorophenate and E-chloronitrobenzene
Chloropicrin
Nitromethane, chlorine and sodium hydroxide
124
-------
Table A-9.
OTHER NITROGENOUS PESTICIDES
Pesticide
Input materials
Captafol
Sodium hydroxide, l,l,2,2-tetrachloroethylsulphenyl
chloride and tetrahydrophthalimide
Cap tan
Sodium hydroxide, trichloromethylsulphenyl chloride
and tetrahydrophthalimide
Folpet
Sodium hydroxide, trichloromethylsulphenyl chloride
and phthalimide
DCAA
Chloroacetyl chloride and diallyamine
Diphenamid
Sodium hydroxide, dimethylcurbamyl chloride and
diphenylmethane
Deet
~-Toluyl chloride and diethylamine
Naphthalam
Phth~lic acid and I-naphthylamine
Methomyl
(Data not available)
Benomyl
(Data not available)
Lethane 384
Butyl "carbitol" chloride and sodium thiocyanate
Methyl isothio-
cyanate
Ethyl chlorocarbamate and N-methyldithiocarbamate
Ni tra lin
Chlorine and ispchtaldodinitrile
Maleic hydrazide
Maleic anhydride and dihydrazine sulfate
Dedine
Dodecyl chloride, sodium cyanide, ammonia and
acetic acid
Pichloram
Chlorine, a-picoline, sulfuric acid and ammonia
125
-------
Table A-lO.
ARSENICAL AND METALLIC PESTICIDES
Pesticide
Organoarsenicals
DSMA
MSMA
Methyl arsenic acid
Cacodylic acid
Organometallics
PMA
Phenyl mercuric oleate
Copper naphthenates
Input materials
Arsenic trioxide, sodium hydroxide, methyl
chloride
DSMA (or materials) and sulfuric acid
DSMA (or materials) and sulfuric acid
DSMA (or materials), sulfur dioxide, sodium
hydroxide, and hydrochloric acid
Mercuric acetate and benzene
Mercuric oleate and benzene
Copper salts and naphthenic acids
126
-------
Table A-ll.
OTHER ORGANIC PESTICIDES
Pesticide
Input materials
Methyl bromide
Methyl alcohol, bromide and sulfur (Alternate:
methyl alcohol and hydrobromic acid)
Endothall
Furan and maleic anhydride (plus reducing or
oxidizing agent)
Bensulide
N-(S-chloroethyl)benzene sulfonamide and
potassium diisopropyl dithiophosphate
EXD
Ethyl alcohol, carbon disulfide, sodium
hydroxide and an oxidizer (HCI or H2S04)
127
-------
Input Material Reference Sources
(1)
Lawless, E. W., R. von R~rnker, and T. L. Ferguson, The Pollution
Potential in Pesticide ~bnufacture, Midwest Research Institute for
the U.S. EPA, Office of Water Programs, Technical Studies Report
No. TS-OO-72-04, June 1972.
(2)
von R~mker, R., E. W. Lawless, and A. F. Meiners, Productio~. Use,
and Environmental Impact Potential of Selected Pesticides, Midwest
Research Institute for Council on Environmental Quality, Contract
EQC-311, Final Report, 15 March 1974.
(3)
Sittig, M., Pesticide Production Processes 1967, Noyes Development
Corporation (1967).
(4)
Sittig, M., Agricultural Chemicals Manufacture, Noyes Development
Corporation, Chemical Process Review No. 52 (1971).
(5 )
Martin, H., Pesticide Manual, British Crop Protection Council,
Second Edition (1972).
.128-
-------
APPENDIX B
U.S. TARIFF COMMISSION LIST OF PESTICIDES
129
-------
PESTICIDES A~[) RELATELJ PRODUcrS. CYCLIC
Fungicid~s:
Bcn:ylbromo acetate
2,6-Bis[dim~thyl~minomcthyl)cvclohexanone
2'-Rromo-4'-hydroxY3c~tuphenone
S-Chloro-2-benwthia:olcthiol, lauryll'yridinium s~1 t
Cyanomethylthioben:othia:ole
2,4-Dichloro-6-(o-chloro~nilino)-s-tri3:ine
1,4 - Dl chlo ro- 2, S-d i methoxyben:cnc [Ch I 0 roneh)
I ,2- Dihydro- 6-ethoxy- 2,2, 4-trimethy lquino lire (Ethox:/quin}
3, S-Di methy 1-1,3,5 - 211- tet r:t!','d roth iad i a: 1 ne- 2 - tin one
(OMIT) .
Diphenylammonium propionate
S-Ethoxy-3-trlchloromcthyl-I.2,4-thi~ia:ole
Hexahydro-I.3,5-trlethyl-s-tria:ine
Hexahydro-I,3 ,5-t ris (e-hydroxyeth,'I) - >-tri a: i ne
2-Hercaptoben:othia:olc, monoethanolamine salt
~tercury fungicides:
Diphenylmercury dodeceny Jstlc-'in~te
Phenylmercuric acetate (r~~)
Phenylmercuric ammoni~~ acetate
Phenylmercuric dimethyldithiocarbamate
Phenylmercuric hydroxide
Phenylmercuric lactate
Phenylmercuric oleate
Phenylmercuric propionate
Phenylmercuric succinate
All other mercury fungicides
Methyl-~-benzimida:ol-2-yl-~-(butylcarbomoyl) c~rbamate
(Benomyl).
2-(I-Methyl-n-heptyl)-4.6-dinitrophenyl crotonate
(Dinocap).
3-(2-Hethylpiperidino)propyl-3.4-dichlorobenzoate
(Pipenl in).
Naphthenic acid, copper salt
Pentachloronitroben:ene (PC~B)
Pentachlorophenol (PCP)
Pentachlorophenol, sodium salt
8-Quinolinol (8-Hydroxyquinoline), copper salt
N-(I,I,2,I-Tetrachloro-ethylsulfenyl)-cis-V-4-cyclo-
hexene-I,2-dicarboximide (Captafol).
2,4,S,6-Tetrachloroisophthalonitrile
2,3,4,6-Tctrachlorophenol
N-Trichloromethylthio-4-cyclohexene-l,Z-dicarboximide
(Capt an) .
N- Trich loromethy I th ioph thai imide (Fo I pet)
2,4,S-Trichlorophenol acid and sat ts:
2,4.S-Trichlorophenol
2,4,S-Trichlorophenol, ethanolamine salt
2,4,S-Trichlorophenol. sodium salt
2,4,6-Trichlorophenol
Herbicides and plant hormones:
4-Amino-3,S,6-trichloropicolinic acid (Picloram)
2,4-Bis(isopropylamjn~)-6-methylthio-s-triazine
(Prometryn) .
S-Bromo- 3-sec-butyl-6-methy I uracl 1 (Bromaci 1)
3-tert-Butyl-S-chloro-6-methyluracil (Terbacil)
N-Butyl-N-ethyl-a,~,a-trifluoro-2.6-dinitro-p-toluidine
(Benefin) .
2-Butynyl-4-chloro-m-chlorocarbanilate (Barban)
2-Chloro-.I,6-bis(ethylamino)-s-tria:ine (Simazine)
2-Chloro-4,6-bis(isopropylamino)-s-triazine (Propazine)
2-Chloro-Z' ,6'-diethyl-~-(n-buto~ymethyl)acetanilide
2-Chloro-2',6'-diethyl-N-(methoxymethyl)acetanilide -
(Alachlor),
2-Chloro-4-ethylamino-6-isopropylamino-s-triazine
(Atrazine) .
2-Chloro-N-isopropylacetanilide (Propachlor)
4-Chloro-2-methylphenoxy butyric acid
N'-(4-Chlorophenoxy)phenyl ~,N-dimethylurea
(Ch 1 oroxuron) .
3- (p-Chlorophenyl)-l.l-dimethylurca (~Ionuron)
3-(p-Chlorophenyl)-I,I-dimethy!urea trichloroacetate
2;S-Dichloro-3-aminobenzoic acid, ammonium salt
2 S-Dichloro-3-aminoben:oic acid, methyl ester
3'6-Dichloro-2-anisic acid (Dicamba)
2:4-Dichlorobcn:yltributylphosphonium chloride
2,S-Dichloro-6-nitroben:oic acid, sodium salt
Source:
4-(2,4-Dichlo", ,,'-~ ..~
3- (3 ,4-Dich loropheny I) -1 ,1-dimethy lurea (DiuronJ. ron)
3-(3,4-0ichlorophcnyl)-I-mcthoxy-I-methylurea (LlnU
2,4-Dichlorophcnyl-4-nitrophcnyl ether (Sitrofen)
3',4'-DichloropropionaniliJe (Propanil) -' Mli)
I, Z-Dihydropyrid:l:ine- 3 ,o-di one pIal de hydraddeJ (,
N-(beta-O,O-Diisopropyl-dithiophosphorylethyl)benzene
sulfonamide (Bensul ide).
N,N-Dimethyl-2,2-diphenylacetamide (Diphenamid)
Dimethyl-2,3,5,6-tctrachloroterephth:llate (DCPA)
Dlnitrobutylphenol (D\SP)
Dinitrobutylphcnol, ammonium salt
Dinitrobutylphcnol, triethanolamine salt
Dinitrocresol, sodium salt
2-Ethylamino-4-isoproprl:Uuno-6-methylmercapto-s-
triazine (Ametrync).
s- Ethyl (cyclohexy 1) ethy 1 th iocarbamat e
S-Ethyl hexahydro-lH-azepine-l-carbothioate (Molinate)
Gibberellic acid
3-Indolebutyric acid
Isopropyl N-(3-chlorophen:'I)carbamate (CIPC)
Isopropyl ~-phenylcarbamate (IPC) .
1-(2-Hethylcyclnhexyl)-3-phenylurea (Slduron)
4-(Methylsulfonyl)-2,6-dinitro-S,S-dipropylaniline
(Nitralin) .
I-Naphthaleneacetic acid and derivatives:
I-Naphthalene acetamide
I-Naphthalene acetic acid (NAA)
I-Naphthaleneacetic acid, sodium salt
N-I-Naphthylphthalamic acid (SPA)
7-0xabicyclo[2.2.1]heptane-2,3-dicarboxylic acid, di-
sodium salt (Endothall).
Phenoxyacetic acid derivatives:
4-Chloro-2-methylphenoxyacetic acid (~PA)
3,S-Oibromo-4-hydroxybenzonitrile, octanoic acid esteI
(Bromoxyniloctanoate).
2,4-Dichlorophenoxyacetic acid (2,4-D)
2,4-Dichlorophenoxyacetic acid esters and salts:
2,4-Dichlorophenoxyacetic acid, 2-butoxyethyl ester-
2,4-Dichlorophenoxyacetic acid, butoxypolypropylene-
glycol ester.
2,4-Dichlorophenoxyacetic
2,4-0ichlorophen0xyacctic
2,4-Dichlorophcnaxyacetic
2 4-Dichlorophenox.acetic
'isopropanoiamine'salt.
2,4-DichlorophenoxfBcetlc acid, iso-octyl ester
2 4-Dichloroohenoxvacetic acid, isopropyl ester
2:4-Dichloropheno~y":~tic acid, lithium salt
2,4-Dichlorophenox)ccetic acid, sodium salt
24 S-TrichloropheJIOXYlcetic acid C2.4,5-T)
2:4:S-Trichlorophenoxyacetic acid esters and salts:
2,4,S-Trichlorophenoxyacetic acid, 2-butoxyethyl
ester.
2,4,S-Trichlorophenoxyacet; ~cid, butoxypoly-
propyleneglycol ester.
2,4,S-Trichlorophenoxyacetic
2,4,S-Trichlorophenoxyacetic
2,4,S-Trichlorophenoxyacetic
2,4,S-Trichlorophenoxyacetic
salt.
Polychloro-tetrahydro-methanoindene (Polychlorodicyclo-
pentadiene) isomers,
2-(2,4,S-Trichlorophenoxy)propionic acid (Silvex)
2-(2,4,S-Trichlorophenoxy)propionic acid esters and
salts:
2-(2,4,S-Trichlorophenoxy)propionic acid, 2-butoxy-
ethyl ester.
2-(2,4,S-Trichlorophenoxy)propionic acid, iso-octyl
ester.
a,a,a-Trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine
(Trifluralin) .
3-(m-Trifluoromethylphcnyl).I,I-dimethylurea
(Fl uomet uron) .
All other cvclic herbicides
Insect attractants and repellents:
tert-Butyl 4(and S)-chloro-2-methylcyclohexanecarboxy-
late (Trimedlure).
acid,
acid,
acid,
acid,
n-butyl ester
sec-butyl ester
dimethylamine salt
ethanolamine and
acid,
acid,
acid,
acid,
n-butyl ester
see-butyl ester
iso-octyl ester
triethylamine
Synthetic Organic
1972, U,S. Tariff
Chemicals,. United States Production and' Sales,
Conunission
13Q
-------
PESTICIDES ~~D rELATED PRODUCTS, CYCLIC--Continued
2-(3.4-Dicnlorophenyl)-1.2.4-oxaJiazoline-4-methyl-
:5,S-dione.
N,N-DiethyltoluamiJe (DEET)
Di-n-propylisocinchomeronate
Insecticides:
:5-sec-Amy I pheny 1-:-;-lI>Cth)"lca rbamate
Bacillus thuringiensis
2-sec-Butyl-4,6-dinitrophenyl-3,3-dimethylacrylate
(Binapacryl) .
2- (p- tert- Butylphenoxy) cyclohexy 1- 2' -propyny I su I fi te
o-sec-Butylphenyl-~-methylcarbamate
Chlorinated insecticides:
Aldrin-toxaphene group:
lIeotach loro-tet rahydro-endo -methanoindene
(Heptachlor) .
Hexachloro-epoxy-octahydro-endo. endo-dimethano-
naphthalene (Endrin).
Hexach loro-epoxy-oct ahydro-endo. exo-d imethano
naphthalene (Dieldrin).
Hexachloro-hexahydro-endo, exo-dimethanonaphthalene
(Aldrin). "
Octachloro-hexahydro-methanoindene (Chlordan)
Toxaphene (Chlorinated camphene)
2,2-Bis(p-chlorophenyl)-1,I-dichloroethane (DDD) (TDE)
a-Bis(p-chlorophenyl)6,S,S-trichloroethane (DOT)
Chlorobenzilate
o-Chlorophenyl-N-methylcarbamate
p-Chlorophenyl 2,4.S-trichlorophenyl sulfone
(Tetradifon) .
Decachlorooctahydro-l.3,4-metheno-2H-cyclobuta-[cd]
pentalen-2-one (Kepone).
1.1-Dichloro-2,2-bis(p-ethylphenyljethane
4.4'-Dichloro-a-trichloromethylben:hydrol (Dicofol)
2,6-Dimethyl-3,S-dichloro-4-pyridinol
Dodecachlorooctahydro-I.3,4-meth~no-2H-cyclobuta-[cd]
pentalene (~Ii rex).
Hexachlorocyclohexane (Benzene hexachloride) (BHC)
Hexachlorocyclohexane, 100% y-isomer (Lindane)
Hexachloro-hexahydro-methano-benzodioxathiepin
3-oxide (Endosul fan) .
Isopropyl 4,4'-dichlorobenzilate (Chloropropylate)
1.l,l-Trichloro-2.2-bis(p-methoxyphenyl)ethane
(~1ethoxych lor) .
2,3-Dihydro-2,2-dimethyl-7-benzofuranly methyl-
carb~~ate (Carbofuran).
m-[[ (Dimethyl amino) methyl ene] amino] phony I methyl carbamate
hydroch loride (1'0 rmetanate hydroch loride) .
m-(l-Ethylpropyl)phenyl methylcarbamate
O-Isopropylphenyl ~-methylcarba~ate
m-(l-Methylbutyl)phenyl methylcarbamate
I-Naphthyl N-methylcarbamate (Carbaryl)
Organophosphorus insecticides:
0-(4-Bromo-Z,S-dichlorophenyl)0-methyl phenylphosphono-
thioate (Leptophos).
4-tert-Butyl-2-chlorophenylmethyl methyJphos-
phoramidi~e.
S-[[(p-Chlorophenyl)thio]methyl] O,O-diethyl phos-
phorodithioate (Carbophenothion).
O,O-Diethyl 0-3-chloro-4-methyl-l-oxo-2H-l-benzo-
pyran-7-yl-phosphorothioate (Coumaphos).
O,O-Diethyl 0-(Z-isopropyl-4-methyl-6-pyrimidinyl)-
phosphorothioate (Dia:inon).
O.O-Diethyl O-(p-(methylsulfinyl)phenyl] phosphoro-
thioate (Fensulfothion).
O,O-Diethyl O-p-nitrophenyl phosphorothioate
(Parathion) .
O,O-Diethyl 0-3,S,6-trichloro-Z pyridyl phosphoro-
thioate.
O,O-Dimethyl 0-[4-(methylthio)-m-tolfl]phosphoro-
thioate (Fenthion).
O,O-Dimethyl O-p-nitrophenyl phosphorothioate (Methyl
parathion).
O,O-Dimethyl S-[4-oxo-l.Z,3-benzotriazin-3(4H)-
ylmethyl] phosphoroJithioate (Azinphosmethyl).
O,O-Dimethyl S-phthalimidomethyl phosphorodithioate
Dimethyl 2,4,S-trichlorophenyl ph05phorothionate
(Ronne I) .
131
Z.3-p-Dioxane S,S-bis(O,O-diethylphosphorodithioate)
(Dioxathion) .
O-Ethyl S-phenylethylphosphonodithioate
a-Methylben:yl 3-(dimethox)~hosphinyloxy)-cis-
crotonate.
0,0,0' ,O'-Tetramethyl O,O'-thiodi-p-phenylene phosphoro.
thioate:
All other organophosphorus insecticides
N-(Phenyl-2-nitropropyl)piperidine
m-Tolyl-N-methylcarbamate
All other cyclic insectlcldes
Nematocides:
O,O-Diethyl 0-(2,4-dichlorophenyl) phosphorothioate
(Dichlofenthion).
O,O-Diethyl 0-2-pyra:inyl phosphorothioate (Thionazin)
Rodenticides:
3-(a-Acetonylben:yl)-4-hydroxycoumarin (Warfarin)
Z-Oiphenylacetyl-l,3-indandione and sodium salt
(Diphacinone) .
2-Pivaloyl-I,3-indandione (Pindone)
Synergists and adjuvants:
a-[Z-(Z-m-Butoxyethoxy)-ethoxy]-4,S-methylenedioxy-2-
propyl toluene (Piperonyl butoxide).
N-(Z-Ethylhexyl)bicyclo)2.2.1)-S-heptene-2,3-di-
carboximide.
1,Z-Methylenedioxy-4-[2-(octyl,ulfinyl)propyl]benrene
Piperonal bis[Z-(Z'-n-butoxyethoxy)ethyl]acetal
(Heliotropin acetal).
All other cyclic pesticides and related products
PESTICIDES AND RELATED PRODUCTS, ACYCLIC
Fungicides:
Bis-I,4-bromoacetoxy-Z-butene
N,N-Bis(phosphonofuethyl)glycine
Cadmium succinate
I-Chloro-2-nitrapropane (Korax)
Copper tall ate
Dimethylthiocarbonyl disulfide
Disodium cyanodithioimidocarba~ate
Dithiocarbamic acid funglcides:
Dimethyldi th iocarbamic acid, ferric saT t (Ferbam)
Dimethyldi thiocarbamic acid, rr.anganese saT t
Dimethyldithiocarba~ic acid, potassium salt
Ethylene bis(dithiocarbaMic acid), diaM.oni~. salt
Ethylene bis(dithiocarbamic acid), disodiUM salt
(Nabam) .
Ethylene bis(dithiocarba~ic acid), manga"ese salt
(Maneb) .
Ethylene bis (di thiocarbamic acid), zinc salt (Zin~)
N-Methyldithiocarbamic acid, sodium salt (S~C)
All other dithiocarbamic acid fungicides
n-Dodecylguanidine acetate (Dodine)
2-Ky.~xypropylmethanethiol sulfonate
Chloromethoxypropylmercuric acetate
Polyethylenethiuram .isulfide (PETD)
Herbicides and plant hormones:
Z-Chloroallyl diethyldithiocarbamate (CDEC)
2-Chloro-N ,N-diallylacetamide rCDM)
(Z-Chloroethyl)phosphonic acid
S-Z,3-Dichloroallyl diisopropylthiolcarbamate
(Dial late) .
2,2-Dichloropropionic acid, sodium salt (Dalapon)
N-Dimethylamino succinamic acid (DMSA)
Dimethylarsinic acid (Cacodylic acid)
Ethyl diisobutyl thiolcarbamated
S-Ethyl N,N-dipropylthiolcarbamate (EPTC)
Ethyl xanthogen di sui fide (BD)
Methanearsonic acid, disodium salt (DS~~)
Methanearsonic acid, dodecyl- and octylammonium salt
Methanearsonic acid, monosodium sal t (~\SMA)
S-Propyl butylethylthiocarbamate (Pebulate)
S-Propyl dipropylthiocarbamate (Vernolate)
S,S,S-Tributyl phosphorotrithioate
Tributyl phosphorotrithioite
Trichloroacetic acid, sodium salt (TeA)
S-Z,Z,3-Trichloroallyl diisopropylthiolcarbamate
(Trial bte).
All other acyclic herbicides
-------
PESTICIDES Al'[) RELATED PROOUCTS, ACYCLlC--Continued
Insecticides:
2-(2-Butoxyethoxy)ethyl thiocyanate
S-~Iethyl N- ( (methy Ica rbamo)' 1 ) OX)'] thl oacet i miJa t e
(~'ethomy I) .
Organophosphorus insecticides:
S-(I,2-Bisl~thox)'c3rbon)'1)ethyl] O,O-Jimeth)'1 phos-
phorodithioate (~lalathion).
2-Carbomethox)'-I-propen-:)'1 Jimeth)'l phosphate
(~'evinphos) .
1,2-Dibromo-2,2-dichlorocthyl dimeth)'l phosphate
(Nal ed) .
O,O-Diethyl S-2-(eth)'lthio)eth)'1 phosphorodithioate
(Disulfoton) .
O,O-Diethyl 0-2-(cthylthio)eth)'1 phosphorothioate
(Demeton 0).
O,0-Diethyl S-(ethylthio)methyl phosphorodithioate
(Phorate).
3-(Dimethoxyphosphin)'loxy)-N,S-dimethyl-cis-
crotonamidc (Dicrotophos).
O,O-Dimethyl 2,2-~ichlorovinyl phosphate (Di-
chlorvos).
O,O-Dimethyl S-(:-ethylsulfinyl)ethyl]phosphoro-
thioate (Oxydemetonmethyl).
O,O-Dimethyl S-(N-methylcarbamoylmethyl)phosphoro-
dithioate (Dimethoate).
Dimethyl phosphate of 3-hydroxy-N-methyl-cis-
crotonamide (~~nocrotophos).
O,S-Dimethyl phosphoramidothioate
0,0,0' ,O'-Tetraethyl S,S'-methylene bisphosphoro-
dithioate (Ethion).
Tetraethyl pyrophosphate (TEPP)
O,O,O,O-Tetra-n-propyl dithiopyrophosphate
All other acyclic insecticides
Nematocides:
O-Ethyl S,S-dipropyl phosphorodithioate
2-Methyl-2(methylthio)propionaldehyde O-(methylcarba-
moyl)oxime (Aldicarb).
Soil conditioners: Polyacrylonitrile,.hydroly:ed.
sodium salt
Soi I fumigants:
1,2-Dibromo-3-chloropropane (DBeP)
1,3-Dichloropropene
1,3-Dichloropropene, 1,2-dichloropropane
Methyl bromide (Bromomethane)
Methyl isothiocyanate
Trichloronitromethane (Chloropicrin)
132
-------
APPENDIX C
STANFORD RESEARCH INSTITUTE LIST OF
PESTICIDES AND PRODUCERS
133
-------
Pesticides
The following revised Pesticides grouping is based upon information received from
producing c()f'1[>i1.nip~ and the 1968 Report (Synthetic Organic Chemicals--U.S. Production and
Sales) of the United States Tariff Commission (issued in July 1970).
Pestici~es dl!d related products are often better known by trade and brand names than
by chemical :13.mr~:",. Maaj' of th~ more common trade and brand names are included (and
cross-rcfer0nced to chemicdl n5mes) below.
Other sources listinry pesticides and related products, particularly their chemical
nam!~~. trac1e 11
-------
3-(4-~c~tonyl~enzyl)-4-hydroxycou~arin
(See: IoIdL"[arin)
J- (#-AcetonylfurfllI:yl) -4-hydroxycoumarin
(See: )-[ 1-furyl-J-acetylethyl ]-Ij-hydroxycoum
-------
Aluminum FhosFhide
Occidental Petroleum Corporation
tlooker Chemical corpo:ation, subsidiary
Electrochemical and Specialties Divisions
Slaja~a Falls, New York
Amibent
aCid)
(See:
)-Amino-2,5-dichlorobenzoic
4-Amino-6-tert-butyl-3-(methylthio)-as-triazin-5(4H]-One'
uaychem Corporation
Chemagro Corporation, division
Kansas City, Missouri
Arninocarb (See:
methylcarbamate)
4-[ Dimethylamino )-m-tolyl
J-Amino-2.5-dichlorobenzoic acid (Amiben)
(Chlorambcn) (Verbigen)
GAF Co::-poration
Ch~mical Diviroion
Texas City, Texas
Rorer-Arrchem
Amchem Products, Inc., division
A~bler, pennsylvania
fLemont, California
St. Joseph, Missouri
(Amibent)
3-Amino-2,5-dichlorohenzoic acid, ammonium
GAF Coq;ocation
Chemical Division
Linden, New Jersey
Rorer-Amchcm
Amchcm Products, Inc., division
Ambler, pennsylvania
CJ.inton, IO'JIa
Fremont, California
. St. Joseph, Mis~ouri
salt
3-Amino-2,5-dichlorobenzoic
GAP corporation
Chemical Division
Linden, New Jersey
acid, ethyl ester
3-Amillo-2.5-rlichlorobenzoic
GAF Corporati-on
Chemicdl Division
Lind~n, New Jersey
acid, methyl ester
3- ,'mil\_)-2. S-,licb lorobenzoic acid, sodium ~al t
G.\f carl,oratinn
Ch'~lIlicdJ. Vivi<.;ion
136
-------
Linden, Ne~ Jersey
3-Amino-s-triazole (3-Amino-l,2.4-triazole)
(Ami trole)
Am~ric~n Cyanamid Company
Agricultural Division
Linden. ~ew Je;sey
i!orer-A:r.cherr.
Amchem Products. Inc., division
Ambler. Pennsylvania
(A TA)
(Cytrol')
4-Amino-3,5,b-trichloropicolinic acid (Picloram)
Dow Ch~mic~l U.S.A.
Freeport. Texas
(Tord on')
Amitrole
(See:
3-Amino-s-triazole)
Ammatcx;
(See:
Ammonium sulfarnate)
Ammonium (benlamidooxy) acetate
Gulf Oil Corpo~ation
Gulf Oil Chemicals Company, division
Industrial and Sp~cialty Chemicals
Pittsburq. Kansas
Division
Ammonium slllfamate (AMS)
E. I. du Pont dB Nemours & Company. Inc.
Industrial Ch€'micals Department
East Chicago. Indiana
Linden. N~~ Jersey
(Ammate')
Ammonium thiocyanate
Amobe n .(S ee:
]-Amino-2,5-dichlorobenzoic acid)
Anthraquinone
Aqualint (See:
Acrolein)
Aquathol (See: 7-0xabicyclo [2.2.1) heptane-2,3-
dicarboxylic acid)
Ars~nic acid
Asponl (See:
Tetra-n-propyl dithiopyrophosphate)
Atratol~ (See: 2-Chloro-4-ethyla~ino-6-isopropyl
amino-:;- tr iazine)
.Hr.ltLone (She: 2-( Ethylamino]-4-[ isopropylami:1O)-
6-~Pthoxy-s-lri~zin~)
137
-------
At ra z ine (See: 2-C hlor 0-4- e th yla[l' ino-6-i5 op rop 11
amino-s- tr iaz ine)
AvaJe xt (See: 5-2, 3-Dichloroally 1 d ii50propyl th io
c.H.bamate)
AvaJex BW' (See: S-2,3,3-Trichloroallyl N,N-
diisopropyl thiolcarbamate)
Azinphosethyl (See: O,O-Diethyl-s-[4-0xo-1,2,3-benzo
tr iaz in-J (4H) -ylmet hy 1 }-phscpho rodi thioate)
Azinphosmcthyl (Spe: O,O-Dimethyl-s-[4-0xo-1,2,3-
bcnzotriazin-J-(4H)-ylmethyl}-phosphorodithioate)
Azodrin' (See~ 3-Uydroxy-H-methyl-cis-croton-
amide-dimethyl phosphate)
Bacillus thuringiensis
Abbott Laboratories
Agricultural/veterinary Products
North Chicago, Illinois
Division
B-rlinel (See:
N-Dimethylarnino succinamic acid)
BIIC (See:
Hexachlorocyclohexane)
Balan' (See: N-Bu t y 1- N- et h y 1-" t, ,- tr ifluoro- 2,6-
dinitro-~-toluidine)
Bclndanel
(See:
Polychlorodicyclopentadiene isomers)
Banvel'D (See:
3,6-Dichloro-o-aoisic acid)
Barban (See:
CdC bar: ita t e)
4'.Chloro- 2-bu tyoyl m-chloro
Baygonl (See:
o-Isopropoxypheny1 methyl carbamate)
Bayl uscide' (See: 2', 5-Dichloro-4' -ni trosalicylanilide,
2-a~inoethanol salt)
Ba y tp x" (S\;!(.!: 0, O-Dir.1e t hy 1 0-[ 4 - (methylthio} -m-tolyl ]
Fhosphorothioate)
Dcnet in (See: N-Butyl-N-ethy I, f, #, #-trif 1uoro-2, 6-
din i t r 0- !' - t C) 1 u i di.ll e )
De;d.,1U'; (S(~(!: 1:(~t~yl-1-r butylcdrbar.:oy1 ]-2-
bCllzi;:!i.ddl.olp. cilrl!d.natn)
138
-------
Bensulide (St'c: N-( '-O.O-Diisopropyldithio-
Fhos?horylethylJ-benzene sulfona~ide)
Benzene h~xdchloride
(5 ee:
Hexachlorocyclohexane)
Benzenesulfonic 3cid. 2,4-dichlorophcnyl ester
(See: 2.4-Dichlorophenyl bcnzenesulfonate)
Benzotriazinedithiophosphoric acid, dimethoxy ester
(S.!C': O.O-Diml::!thyl s-[ 4-oxo-1,2. )-benzotriazin-J
(411) -ylmethyl J phosphorodithioate)
DCllzylbromoacetate
r.~rck & Co., Inc.
Merck Chemical Division
Hawthorne, New Jersey
0- Benz y l-p-ch lorophenol (4-Chlor 0-'-
pheny l-o-cresol)
Monsanto Company
Mons~nto Industrial Chemicals Company.
Sau1ct. Illinois (Santophen It)
Red Devil Paint Co.
Tacoma. Washington
cis, trans-(5-Senzyl-3-furyl) methyl 2.~-dimethyl-J-
(2-met h y 1 {Jro peny l) cyc 10 pro p aoec arboxylate
CPC International. Inc.
S. B. Penick & Company. division
Lyndhurst, ~ew Jersey
Bf'nzy 1 rhoddllide (See:
Benzyl thiocyanate)
B~ tasan II (See: N-( '-0, O-D iisopropy Idi thio phosphor y1
ethyl] benzene sulfonamide) .
Bexide
(See:
Diethyl dithiobis (thioooformate)
l3idrinr (See: 3-( Dimet hoxypbosphinyloxy ]-N. N-
dim~t h y l-cis-crotolldmid e)
Biphenyl
Bis~1,4-bromo~cetoxy-2-butene
2,3,4. ')-Ois (#2-butylene) tetrahydrofurfural (Repellent 11)
~cLaug~lin Gormley King Company
Minneapolis. Minnesota
o.o-'3is (p-chloroph~nyl) acp.timidoylphost'hor-
amiJoLtI ioa t,~
H-,\,ch...:n c0q.o(atioll
139
-------
Chemagro corporation, division
Kansas City, Missouri
(Gophacide')
I,'-Bis (p-chlorophenyl)
(Sec: DDT)
t,t,t-trichloroethane
1,1-0is (p-chlorophenyl)-2,2,2-trichloroethanol
(See: 4,4'-Dichloro-'-[trichloromethylJ benzhydrol)
Dis (diethyltl.iocarbamoyl) disulfide
2,6-6i5 (dim'~thylamillo:nethyl)
Merck & Co., Inc.
Merck Ch~mical Division
Hawthorne, New Jersey
cyclohexanone
Bis (dimethylthiocaroamoyl) disulfide
Bis (dimethylthiocarbamoyl) sulfide
S,s-ois (2,3-p-dioxanedithiol) O,O-diethyl-
pho5phorodithioate (See: p-Dioxane-2,3-diyl
ethyl. phos.phorodit.hioate)
S-(1,2-ais [ethoxycarbonyl) ethyl) O,o-dimethyl
phosphorodithioate (See: Malat.hion)
2,4-0is (cthylamino)-~-chloro-s-triazine
(See: Simaz Lnc)
2,4-0is (isopropylamino)-6-chloro-s-triazine (See:
2-ehloro-4,6-bis (isopropylamino)-s-triazine)
2,4-8is (isopropylamino)-6-methoxy-s-triazine (See:
2-Met~oxy-4,6-bis (isoprcpylamino]-l,J,5-triazine)
2,4-Bis (isopropylamino)-b-methylthio-s-triazine
(Gesagard) (2- Meth y Imc rca~to- 4,6- b is-[ Iso pro py lamino J-
s-t.riazine) (Primazc) (prometryne)
eiba-Geigy corporation
. Agricu~tural Division
McIntosh, Alabama
(CaparoH)
2.2-nis (p-:n(~thoxyphcnyl) 1,1, 1-trichloroethane
(Sel.!: 1,1, l-Tr ichloro-L, 2-bis ( p-methoxyphenyl]
ethant.')
Bis (t-'entdchloro-2. 4-cycloper:t<.ldien-1-yl)
(3\)"': Decdch lOl.ollis (l., 4-cyclo[>€ot
-------
Bis (tri-n-butyltin) oxide (Oxybis
Americdn Cdn Company
M&T Cbemicals Inc., subsidiary
Ca.rrollton, Kentucky
Cincinndti IHlacron Inc.
Cincinnati lIilacron Chemicals
Clncinnati, Ohio
[ tributyltin)
(TBTOO)
Inc., subsidiary
(Car-Ban#T-O Biostat)
800;yl' (SPi!: Dimethyl J-hydroxyglutaconate
dimHthyl ~hosphate)
IJord::;cu*
(See:
Sod,ium bora tes)
Bo:ax' (See:
Sodium borates)
Boro-spray. (See:
Sodium borates)
Bramo lcide- (See: ( 2,4, 5-Trichlorophenoxy)
acetic acid dnd iso-octyl ester)
Dromacil (See:
5-Bromo-)-scc-butyl-6-methyluraci1)
8romo.cetyl bromide
Aldrich Chemical Company. Inc.
/1ilwallke~, Wisconsin
5- BroPlo- J-sec- bu t y 1- 6-me th y 1 u rac il (Bromaci 1)
(Isoc il)
E. I. dll Pont de Nemours & Company, Inc.
Dioche!T.ica.ls Department
La Porte, Texas
(HyvarO)
O-(4-Bromo-2,S-dichlorophenyl)-O-methyl phenylphosphorothioate
(L",ptophos)
Northwest Indu;:;tries, Inc.
Velsicol Chemical corporation, subsidiary
Dayport, Texas
2-nromo-4'-hyJroxyacetophenone
Buckllldn Laboratories, Inc.
, Cadet, /1issouri
Mumphis~ Tennessee
141
-------
Bromomrthane (~ethyl bromide)
Annual Capacity
lnilli2D~-2I-f2[DdsL
Do~ Chc~ical U.S.A.
~idland. Michigan
Great Ldkcs Chemical corporation
El Dorado. Arkansas
Kerr-~cG~0 corporation
Kerr-i'lcLI(!e Chemical corp.. subsidiary
Trona. California
North~e~l Industries. Inc.
/lichlgan Chemical Corporation. subsidiary
St. Louis. Michlgan (Pestmaster~)
15.0
10.0
1.3
TOTAL
5.0
31.3
Sour:ce:
Chemical /lar:keting Reporter. september 18. 1972.
Dromoxynil (See:
3.S-Dibromo-4-hydroxybenzonitrile)
Bulan' (See:
Dilan.)
Busan'
(See:
Cyanodithioimidocarbonic acid. sodium salt)
Butacidei (See:
Butoxoncli
acid)
(See:
Piperonyl butoxide)
4-(2.4-Dichlorophenoxy] butyric
'-(2-[2-n-Butoxyethoxy)-ethoxy)-4,S-rnethylenedioxy-
2-pr:o?yltoluene (See: Piperonyl butoxide)
2- (2-outoxyethoxy) ethyl thiocyanate (#-Btltoxy-'-
thiocyanojiethyl ether) (Thiocyanic acid, 2-
r~-LutoXY0thoxYJ ethyl ester)
Blue Spr:uce Compaay
i:;,lison. New Jersey
Rollm un,1 Haas Company
Bristol. Pennsylvania
(Lethanet)
Butoxypolypr:opylene glycol
Union Carbide corporation
Chc~icals and Plastics Division
Institute and South Charlest
(Stabilene#)
.-nut.oxy- ;-lh ivr;yallodiethyl ether (See: 2-( 2-
31Jtoxy,!thvxyJ et:lyl U.iocyanate)
142
-------
Butylate (See:
S-Ethyl diisobutylthiocarbamate)
2-tert-!3utylamino-4-cthylamino-6-mpthylthio-
s-triazine
<':iba-Geigy corporation
AqLicultural Division
~clnto$h, Alabama
(Igran 80WI)
But y lcarbi ty 1 (I)-propyl piptHonyl) ether
(Se~: l?ipp.conyl butoxide)
3-tert-~utyl-S-chloro-6-methyluracil (Terbacil)
E. I. du Pont de Nemours & Company, Inc.
BiochemicaLs Department
La Porte, Texas
(Sinbari)
0- (4-tert-J3utyl-2-chlorophenyl) a-methyl methyl-
phosphoramidat~ (Methylphosphoramidic acid,
4-tert-butyl-2~chlorophenyl methyl ester)
Dow Chemical U.S.A.
Midland, Michigan
(Ruelenet)
2-sec- Bu t y 1-4, 6-dinitro phenol (C hem-ox)
(Dinoseb) (DNBP) (DNJSBP) (4,6-Dinitro-o-sec-
bu t yl phpno 1) (4,6- D init rophenol- 2-sec-buty lp henol)
Blue SprDcP Company
Edison, New Jersey
Dow Chemical U.S.A.
Midland, Michigan
2-scc-Uutyl-4,6-dinitrophenol. alkanolamine salt
Dow Cheinical U.S./\.
Midland, Michigan
2-sec-j3utyl-4.6-dinitrophenol, ammonium salt
FMC Corpora lion
Chcmical Group
~gricultural Chemical Division
. Middleport, New York (Sinoxl General)
2-sec-Butyl-4.6-dinitrophenol, isopropanolamine salt
Blue Spruce company
Edison, New Jersey
2-sec-Butyl-4,6-dinitrophenol, triethanolamine salt
Blue Spruce Company
Edison. ~cw Jersey
n:c carpor,l tion
Ch0:aical Gr:o~!P
Agricultural Chemic~l Division
~idJ10port, New York
(SinonPE)
143
-------
2-sec-Outyl-Q,6-dinitrophenyl isopropyl carbonate
(See: Dinobu ton)
N-Sutyl-N-ethyl-',J,.-trifluoro-2,6-dinitro-p-
toluidine (EJ<.!nC'fin)
Eli Lilly and C0mpany
Tippecanoe Laboratories
La[dy~tte, Indiana
(Balan' )
2- (p-tert-butj'lphenoxy) cyclohexy~ propynl sulfite
2-Butynyl-4-chlorocarbanilate
(See: 4-Chl uro- 2- bu tyny l-m-chlo rocarbanilate)
Butyrac' (See:
butyric acid)
Q-[2,4-Dichlorophenoxy]
BUX (Mixture of m[ 1-~ethylbutyl) phenyl-
methylcarbamdte [75~] and m( l-Ethylpropyl]
methylcarbamate [25~])
Standard Oil Company of California
Chevron Cbemical Company, subsidiary
Ortho Division
Fort Madison, Iowa
pbenyl-
(BUx 'Ien')
CDAA (See:
2-Chloro-N,N-diallylacetamide)
2-Chluroallyl diethyldithiocarbamate)
CDEC (See:
CIPC (See:
Isopropyl 3-chlorocarbanilate)
CMA (See: Methanearsonic acid, calcium and
acid calcium salts)
C:10 (See:
3-rp-~hlorophenyl]-1,1-dimethylurea)
4-CPA (See:
p-Chlorophenoxyacetic acid)
Cacodylic acid (Dimethylarsinic
dim~thylarsinu oxide)
The Ansul Company
Chemical Division
Marinette, Wisconsin
acid)
(Hydroxy-
(Phytart 560)
Cacodylic acid, sodium salt
Cad~iu~ succinate
~dllinckrorlt Chemical works
Industrial Chemicals Division
st. Louis, i~lzsouri
r.:al.lr~
(:.;ee:
:1cthan~u.rsonic
acid, calcium
144
-------
acid salt)
Calcium acid methyl arsonate
aciJ. calcium acid salt)
(See:
r.ethanearsonic
Calcium ilC5cnate
Ch~mp~r Ch~micdl co., Inc.
Po~tland. Oregon
Los Anqcl~9 Chemical company
South Gate, california
['('unwalt cor?ordtion
Chemical Division
Bryan, Texas
Calo-clo!:, (See:
Mercury bichloride)
Calocure'
(Sec:
r.ercury bichloride)
Cantrol (See:
acid)
4-[2-r.ethyl-4-chlorophenoxy] ~utyric
CaparoH (See: 2,4-Bis (isopropylamino ]-6-
methylthio-s-triazine)
Captan (N-[Trichloromethylthio)-q-cyclohexene-
1,2-dicdrboxi~ide) (N-Trichloromethylthiotetra-
hydrophthalimid~) (n[Trichloromethylmercapto~4-
cyclohexene-l,2-1icarboximice)
Standdrd Oil Company of california
Chpvron Chemical Co~p.~y, subsidiary
Ortho DivisioOl
. Peery, Ohio
Stauffer Chemical Com~any
Calhio Chemicals, Inc., subsidiary
Pp.rry, Ohio
Car-Bani T-O Biostat (See:
buty Hin) oxide)
Bis (tr i-n-
caebaryl (See:
l-Naphthyl N-methylcarbamate)
carbofuran (See: 2,3-Dihydro-2,2-dimethyl-7-
benzofuranyl methylcarbamate)
2-Carbomethoxy-l-methylvinyl dimethyl phosphate.
. i::;ol~er (See: O,O-Dimethyl 0-( 2-carbomethoxy-l-
methylvinyl) ~hosphatc)
Carbon bisulfide (See:
Carbon disulfid~)
145
-------
Carbon disulfide
Carbon tetrdcbloridc
Carbophenothion (See: O.O-Diethyl-S-p-chloro-
pheny 1 th iO!T\cthy 1 phosphorodi thioa te)
Z-Carboxymethoxy-l-rnethylvinyl dimethyl
pho~phate (S~e: O.a-DimethylO-(2-carbomethoxy-
1-mrthylvinylJ phosphate)
Car;'YI1~' (Sec:
c
-------
Chlorinat~d camphene (Se~:
Toxaphene)
Chlorobenlililte (See:
Ethyl 4,4'-dichlorob~nzilate)
S-Chl or 0-:2 - b,mzot It ia zol et hio I, 1 a ur yIp yr B. ini tlm
sa It (Sce: 5-Ch loro- 2-merca ptobenzo thiazo Ie,
laurylpyrldinium salt)
2-Chloro-4,b-bis (diethylamino)-s-triazine
Chlorazinc)
(See:
2-Chloro~4,6-his (ethylamino)-s-triazine (See:
Simazine)
2-Chloro-4,6-bis (isopropylami~Qj-s-triazine (2,4-Bis
[isopropylamino]-6-chloro-s-triazine) (Propazine)
eiba-Geigy corporation
Agricultural Division
~clntosh, Alabama
(l'Iilogardt)
S-Chloro-3-tert-butyl-6-methyluracil (See:
Butyl-5-chloro-6-methyluracil)
.3-tert-
4-Chlo~o-2-butynyl m-chlorocarbanilate (Barban)
(4-~hlcro-2-butynyl N-( 3-chlorophenyl] carbamate)
(m-Ch lorocar barlll ic aci d, 4-c hloro-2-blityn y 1 ester)
Gulf Oil Corporation
Gulf Oil UI!~1rticdls company, division
Industrial and Specialty Chemicals Division
Pittsburg, KanSdS (Carbynet)
3-Chlorocarhanilic acid, isopropyl ester
(See: Isopropyl 3-chlorocarbanihte)
2-ChlorO-N,N-diallylacetamide (CDAA) (N,N-Diallyl-
2-chlcroaceta~ide)
MonSanto Company
Monsanto Commercial Products Company
'Agricultural Division
:-\uscatine, Iowa
(Randoxl)
0- (2-Chlor-o- 1-( 2,S-dichlorophenyl] vinyl) 0,0-
diethyl ~~~sphor-othioate (See: o,O-Diethyl 0-[2-
chloro-l- (2, S-dichlorophenyl) vinyl] phosphorothioate)
2-Chloro-2-dietltylcarbamoyl-1-metbylvinyl dimethyl
~hosphatc (See: Phospharr.idon),
2-Chloro-L,6~-diethyl-N-butoxymethyl acetanilide
Monsanto Company
Monsanto ~oru~ercii\l Products Company
Agriculturdl ~ivision
147
-------
/'\u:>catine, Iowa
2-Chloro-2,6'-diethyl-N-(methoxymethyl)
Monsanto Corrp.lny
l1onsanto Co:~:nercial Products Company
Agricultural Division
l1usciltine, Iowa
St. Louis, Missouri
acetanilide
(Lasso')
2-Chloro-4-cthylamino-6-isopropylamino-
triazine (AtrdZin€)
C iha- G elgy Corp'ora tion
Agricultural Division
McIntosh, Alabama
(AAtrext)
(Atra toU)
St. Gabriel, Louisiana
2-(4-Chloro-6-cthylamino-s-triazin-2-ylamino)-2-
methylpropionitrile
Shell Chemical Conpany
Agricultural Division
Denver, Colorado
(Bladex t)
Chloroethylm~rcury (See:
Ethylmercury chloride)
2-Chloroethyl.phosphonic acid (Ethrel')
;!or~r-Amchem
Amchem Products, Inc., division
Ambler, Pennsylvania
(Ethrel t)
2-Chloroethyltrim~thyl a~monium
American CYdnamid Company
Agricultural ~ivision
Linden, New Jer~ey
chloride
(cycoceH)
Chlorofenson (See:
benzenesulfonate)
p-Chlorophenyl p-chloro-
Chloro IPC (See:
Isopro~yl-3-chlorocarbanilate)
2-Chlot"o-N-isopt"opyl aceta!1ilide
Monsanto Company
Monsdllto Co,n:ncrcial pt"oducts
. Agricultut"al Division
l1u$catine, Iowa
(Pt"opachlor)
Company
(Ramrod #)
Chloromethoxypropylmercuric acetate
Troy Chcmicdl Cot"poration
New3rk, New Jersey
0- (J-L"h 10 ["0- 4-1T1,~t1: Y 1- 2 - 0 xo- 2H-1- benzo py rdn-
7-1'1) U,'J,-Ji..thylpr.osphorothioate (S~c: O,C-
'lLf8'
-------
Diethyl O-rn-chloro-U-methyl-2-oxo-2H-1-
benzopyriin-7-yl) phosphorothio'lte)
4-Chlol"O-2-D1othyll'hcno:
-------
La Porte, Texas
(Telvar')
J-(p-Chlorophenyl)-1,1-dimelhylurea
acetate (MonUL"On '1'CA)
Allied Ch'">I~icdl corporation
Union Texas Petroleum Division
Agricultural Department
Balliwore, Maryland
trichloro-
(Uro:d)
Chloropheny lnaercury (Sef?:
Phenylmercury chloride)
2-«(p-Chlorophenyl)phenyl acetyl)-1,J-indandione
(See: Chlorophacinone)
5- ([ (p-Chlor:ophenyl) tHo] methyi) O,O-dimethyl
phosphoroJithiodte (See: O,O-Dimethyl 5-( p-
cblorophenylthio] methyl phosphorodithioate)
S-(p-ChlorQphcnylthio) methylo,O-diethyl
phosphoroJithiodte (S~~: O,O-Diethyl S-(p-
chlorophenylthiomethyl) Fhosphorodit~ioate) .
Chloropicrin (Nilr och 1 oroform) (T r ieh loronitromethane)
Dow Chemical rJ.S.A.
~ittsbucg, California
Great Lakes Chemical corporation
El DoraJo, Ar:kansas
Niklor Chemical Company, Inc.
Lonq Beach, California
Sobin Chemicals, Inc.
arrington, Maine
(Chlor-a-pic')
Chloropropylatc~ (See:
Isopropyl 4,4'-dichlorobenzilate)
" .
(4-Chloro-o-tolyloxy) acetic acid' (MCP) (I1CPA)
(2-Metbyl-4-chlorophenoxyacetic acid) (4-Chloro-2-methyl-
phcnoxyac~tic acid)
Rhodia Inc.
Chipman Division
Portland, Oregon
Transvadl, Inc.
Jacksonville, Arkansas
(4-Chloro-o-tolyloxy) acetic acid, salts (unspec{fied)
Rhodia rnc.
Chipman Division
Portland, Oregon
2-Chloro-1- (2,4, 5-trichlorophenyl) vinyl dir:ethyl
pho::;pha t,! (See: Dio1<)t ~IY 1-1-[ 2,4, 5-tr ichloroph€'nyl)-
2 - r.;~; 1 C L" l)V in yip It 0 s ph a t. e)
15Q
-------
<.:hloroxuron (See:
3.N-din,~t~ylure~)
N'-[ U-Chlorophcnoxy] phenyl-
Chlor?hcn~nidinc (Ser: ~,N-Dimethyl-N'-(2-methyl-
4-chlorop~enyl]-for~a~iJine)
Chl~lphos (Sec: O.O-Dimethyl 2,2,2-trichloro-1-
hydroxy~thyl phosphonatc)
<.:h lor propha:n (Se~:
Isopropyl-3-chlorobanilate)
Clodrin' (Sf's: O,O-Di'11ethyl 0-( 1-metllyl-2-
(1-pheny lcarbethoxy) vinyl) r:hospha te)
Copper acp.tate (Cupric acetate)
Allied <.:hemical corporation
Specidlty Chemicals Division
~drcus Hook, Pennsylvania
Cucmetrcll Corporation
Chemicals Group
Inorganic Chpmicals Division
Cleveland, Ohio
C. P. Chemicals, Inc.
Sewar~n, New Jersey
Filo Color and Chemical Corporation
Nc~ark, N~w Jersey
"ineral Research and Develupment Corp.
Concord, North Cdrolina
Richardson-~errcll, Inc.
J. T. Ddkcr C~emical Co., subsidiary
Phillipsburg, New Jersey
The Shepherd Chemical Company
Cincinnati. Ohio
Union, Carbide corporation
Chemicals and Plastics Division
Niagara Palls, New York
Coppe~ aceto~rsenite
Copper carbonate
Copper-8-hydroxY1uinolinate (See:
copper salt)
8- Qu ino 1inol.
Copper naphthenate (Cupric naphthenate)
Cnemical Formulators, Inc.
Chemical Division
Nitro. ~est Virginia
Cincirlll
-------
Ferro Chemical Division
ScHord, Ohio
Mobil oil corporation
North American Division
Torr
-------
Buckman Laboratories, Inc.
Cauet, :1issouri
M(,I~phi~, Tcr1!l€'ssee
cyclic et hylene (diethoxyphosphinyl)
carbonate
. A~crican CYdnu~id Company
Aqricultutal Division
Lind~n, Se~ Jersey
dithioirr.ido-
(cyolane ')
Cycloate (Se~:
carbamate)
S-Ethyl /i-ethyl-/i-cyclohexylthio-
cycoceH (See: 2-Chloroethyltrimethy1
azr"non ium cn loride)
Cyqon' (See: 0, O-Dimet hyl S-[ N-methy1carbamoyl-
methyl) phosphorodithioate)
Cyo1ane' (See: Cyclic ethylene [diethoxy phosphinyl ]
dithioimidocarbonate)
Cyprcxll (Set!:
Dodecylguanidine acetate)
2,4-D (See:
(2,4-Dichlorophenoxy] acetic acid)
2,4-D(j (Sec:
4-[2,4-Dichlorophenoxy) butyric acid)
4- (2, 4-D3)
(See:
4-[2,4-Dichlorophenoxy] tutyric acid)
Dacp (See:
1,2-Dibromo-3-ch1oropropane)
DCMU (See:
J-(J,4-Dichlorophenyl]-1,1-dimethylurea)
DCliA (See:
2,6-Dichloco-4-nitroaniline)
DCPA (See:
Dimethyl tetrachloroterephthalate)
1, )-Bi5 [ 1-hydroxy-2, 2, 2-trichloroethyl]
DCU (See:
urea)
DD mixture (See:
dichloropropane)
1,3-Dichloropropene, 1,2-
153
-------
DUT (1,l,1-Trichloro-2.2-bis (p-cblorophenyl) ethane)
(ct,lloroph.'/IIJ t::dne) (t, J-!Jis [p-chloropheny l) .. I, J-
trlch lorocth <1oe) (Dich 1 0 radip heny 1 tr ichloroet hane)
Annual capacity
J~illio~_Qi-RQ~dsl
Montrose Chemical corporation of California
Torrdnce, California
TOTAL
85
85
Note:
Not currently producing.
Sources:
oil, Paint and Drug Reporter, January 4, 1971, and correspondence.
DDVP (See:
2,2-Dichlorovinyl dimethyl phosphate)
D!:.T (See:
N,N-Diethyl-m-toluamide)
Dehydroacetic acid)
DHA (See:
DrlDT (See:,
ethane)
1,1,1-Trichloro-2,2-bis (p-methoxyphenyl)
DriP (See:
Dimethyl phthalate under Plasticizers)
DMTT (Sec: J,S-Dimethyl-1,3,S,2H-tetrahydrothia-
diazine-2-thione).
D/1l1 (Se.£!:
3-[3,4-Dichlorophenyl)-1,1-dimethylurea)
DN3P (See:
2-sec-Butyl-4,6-dinitrophenol)
DNC (~ce:
4,&-Dinitro-o-cresol)
DNOSBP (See:
2-sec-Butyl-4,6-dinitrophenol)
2-(2,4-Dichlorophenoxy) propionic
2,4-DP (See:
aci~)
DS/1A (See:
Methanearsonicacid, disodium salt)
Daca~in(d (See: (2,4-Dichlorophenoxy) acetic
aciG, oil soluble diamine)
Dacthal;
(Se~:
Dimcthy~ tetrachloroterephthalate)
Dd L.I,}''>i1~
(S2L' :
2,2-Dichloropropionic acid, sodium
154
-------
sa 1 t)
D~sanitr (See: O,o,-Ciethyl O-p-(methylsulfinyl]
phenyl phcspho~othioate)
D~zomet (Se~: 3,5-Dimcthyl-1,3,S,2H-tet~ahydrothia-
di~zine-2-thione)
DeC3C hlorobis (2, 4-cyc 10 pent adiene- 1- yl)
(ais [pcntacblnro-2,4-cyclopentadien-1-yl])
Occidental Petroleum Co~poration
Hooker Chemical Corporation, subsidiary
Electl"ucheiTlical and Specialties Divisions
Nia'Jara Falls, New York (pentac Tl'!t)
Decachloro-octdhyaro-1,J,4-rnetheno-2H-
cyclobuta [CD] pentalene-2-one
Allied Chemical corporation
Plastic~ Division
Hopewell, Virginia
Dechlo~ane (See: Dodecachloro-octahydro-1,3.4-
metheno-2U-cyclobuta [cd J pentalene)
DEET (See:
N,N-Diethyl-m-toluamide)
DEF'#
(See:
S,S,S-Tributyl phosphorotrithioate)
Dehydroacetic acid
Delnav# (See:
dithioate)
p-Dioxane-2,3-diyl ethyl phosphoro-
Demeton (Sec: O,O-Diethyl a [and S]-2-(etbyltbio]
ethyl phosphorothioates)
Demeton-S-methyl (See: O,O-Dimethyl S-2-(ethylsulfinyl]
ethyl ,['hospho~odithioate)
Demosanlt tJ5\l (Spe:
di me t hox y bell zE'ne)
1,4-Dicbloro-2,S-
Des~in!< (See:
Dinobuton)
Dethmo~#
(See:
Warfarin)
Dexonll (See: p-DilTlethylaminobenzenediazosulfonic
acid, so
-------
methyl-6-pyri~idinylJ phosphorothioate)
Dibenzo " 4-thiazine (See:
Phenothiazine)
1,2-Dibromo-J-chloropropane
Dow Chcmic~l U.S.A.
~idland, Michigan
Shell Chc~ical Company
Agricultural Division
Denv~r, Colorado
(DaCP)
(Nemagon')
1.2-Dibro~o-2,2-jichloroethyl dimethyl phosphate
(Sec: O,O-Dimethll 0-( 1,2-dibromo-2.2-dichloroethyl]
phosphat~)
1,2-Dibromocthane (See:
Ethylene dibromide )
J.5-Dibromo-4-hydroxybenzonitrile
Rhodia Inc.
Chipman Division
Portland. Oregon
(Bromoxynil)
Di-n-butyl ~uccinate
Glenn Chemical company, Inc.
chicago. Illinois
(T"abatrexl)
Dicamba (See:
J.6-Dichloro-o-anisic acid)
Dicapthon (See: 0-2-Chloro-4-nitrophenyl 0,0-
diethyl"pho::ophorothioate)
S-(1,2-Dicarbethoxyethyl)-O,0-dimethyl
dithiopho»pltate (Si:!e: Malathion)
Dichlone (2,J-Dichloro-1.4-naphthoquinone)
PMC cori'oration
Chemica! Group
"Agricultural Chemical Division
~iddl~port. Ne~ York
2.5-Dichloro-J-aminobenzoic acid, ammonium salt
(5e;.: J-r.mino-2,5-dichlorobenzoic acid, ammonium salt)
3,6-Dichloro-o-anisic acid (Dicamba)
North\li:!st Industries. Inc.
Velsicol Chemical Corporation, subsidiary
Chattanooga, Tennessee (BanveltD)
PDI-Gordon corporation
Kdn~~s city, Kansas
(Trimec t)
156
-------
p-Dichlorobcnzene
Annual Capacity
jfil11ioD~-2I-~QliD£~l
___~!!!arks
Allied Chemical corporation
In(lustriJ 1 Chemicals Division
Syr,H:usc (Solvay), New York
Cbemic~l rroJucts corporation
curtersville, Georgia
Dow Chemical U.S.A.
r.idl
-------
2,~-Dichloro-6-(o-chloroaniline)-s-triazine
Udychem Corpordtion
Chem~~ro corporation, division
K~nsas City, Missouri
(Dyrene#)
1,4-Dichloro-Z,5-dimethoxybenzene (Chloroneb)
E. I. du Pont de Nemours & Company, Inc.
Inuustrial Chemicals Department
Linuen, NeW' Jersey
(Demosan' 6511)
3, 5-Dich loro-N- (1, 1-dimethyl-2-propanyl)
Robm and Haas Company
Philadelphia, Pennsylvania
benzamide
Dichlorouiphenyltrichloroethane (See:
DDT)
1,2-Dichloroethane (See: Ethylene dichloride in
general alphabetical listing)
2, J- Dich loro- 1, 4-na ph t h oqu inone (See:
Dichlone)
2,b-Dichloro-4-nitroaniline (1-Amino-2,6-dicbloro-
II-ni t z:obe:1zenc)
GAP' Corporation
Chemical Division
Renssela~r, NeW' York
Keviinee Oi 1 Co.n1'any
Harshaw Chemical Company, division
Pi<]fT,ent alld Ceramic Dp.partment
Louisville, Kent~cky
The Shez:win-Williams Co.
Sberwin-Hillialns Chemicals Division
St. Burnard, Ohio
Dichloronitrobenzoic acid, isometric mixture
GAF corporation
Chemical Di.ision
Linden, New Jersey
2',5-Dichloro-4'-nitrosalicylanilide
Baychem Corporation
Chema~ro Corporation, division
Kansas City, Missouri
(Yomesan')
(Yomesan')
2',5-Dichloro-Q'-nitrosalicylanilide, 2-amino-
ethanol suIt (Z'-5-Dichloro-4'-nitrosalicylanilide
amine) (Chlonitralid) (Yomesan)
Baychem Corporation
Chemayro Co~poration, division
Kansas city, Missouri
(Bayluscidet)
2, '1- D iej, lo[:o phenol, hen zp.!\es Ul Eona t e
(See:
2,4-
158
ethanol-
-------
Dichlorop!.('n y 1 benzent:su: fona tt:')
(2,4-Dichloroph0noxy)acetic acid
~o~ Ch0~icul U.S.h.
~; i j 1 a:1
-------
(2,4-Dichloroph~noxy)acetic
Dow Chcmicdl U.S.A.
:'IidiallG, ~icnigan
Rhodia Inc.
Chipman [Ii vision
Portland, Oregon
(2,4-Dichloro~henoxy)acetic acid, dimethylamine salt
Alco StanGdrd Cor?oration
Mill~r Ch~mical and fertilizer corporation, subsidiary
Hanover, pennsylvania
Chempar Chemical Co., Inc.
POl:tlaud, Oregon
Dow Chemical U.S.A.
Midland, ~ichigan
North American Philips Corp.
PEPI, Inc., subsidiary
Thompsor,-ilay..ard Chemical COl'1pany, subsidiary
Kansa~; City, Kansas
Hew O~leans, Louisiana
PBI-Gordon corporation
Kansas City, Kansas
Rhodia Inc.
Chi~man Division
PortlarHl, Ol:cgon
Riverdal~ Cb~mical Company
Chicago Heights, Illinois
ROl:er-Atrc!lf;>m
Amchem Products, Inc., division
Ambler, Pennsylvania
Fremont, California
, St. Joseph, Missouri
Transvaal, Inc.
, Jacksonville, Arkansas
acid, see-butyl ester
(2,4-Dichlorophenoxy)acetic acid, N,N-dimethyl oleyl/linoleyl
amine salt
Tl:ansvaal, Inc.
. Jacksonville, Arkansas
(2,4-Dichlorophcnoxy)acetic
isopropanolamine salts
Dow Chemical U.S.A.
, Midland, Michigan
acid, ethanolamine and
(2,4-Dichlorophenoxy) acetic acid, ethyl ester
Rore r- A Ir.ch em
AlliCheln ?["oducts, Inc., division
AI':blet, Pt>nnsyl vania
FU"".Jnt, Lalih1rnia
St. Ju_,~ph, Missouri'
16Q
-------
(2,U-DichlorofJh~nox).)acctic acid, 2-
ethylhexyl ester (See: (2,4-Cichlorophen0xy]
acetic acid, iso-octyl ester)
(2,4-Dich~~rophe~oxy)acetic acid, iso-octyl ester
(r2,~-Jic~luroph~noxy]-acetic acid, 2-ethylhexyl ester)
C~t'iT'p.H' Ch0.:"ical Co., Inc.
Portland, Oregon
Dolo' Ch('mica.l U.S..\.
Midland, Michigan
North Ame::-ica!1 Philip~ Corp.
PEPI, Inc., subsidia ry
Ihorrpson-ildp/ctrd Chemical Company, subsidiary
K~nsas City, Kansas
PBI-Goe-don Coe-poration
Kan~as city, Kansas
Rhodia Inc.
Chipman Division
Portland, Oregon
Riverd.1le Chei'1icdl Company
Chicdgo Heights, Illinois
Rorer- Alrchem
Amchcm Products, Inc., division
Ambler, Pennsylvania
Fremont, California
St. Jo~eph, Missouri
Tran:3vaal, Inc.
Jac~sonvill~, Arkansas
(2,U-Dichloruphenoxy)acetic acid,
Chempar Chen:ical Co.. Inc.
Portland, Oregon
Dow Chemical U.S.A.
Midland, 11 ichigan
niverddle Chemical Company
Chicago Heights, Illinois
Transvildl, Inc.
JacKsonville, Arkansas
isopropyl ester
(2,4-Dichlurophenoxy) acetic acid,
.\lco 5til/lllard CorfJoration
Miller Chemical and fertilizer
Hanover, Pennsylvania
D~W Chemical U.S.A.
~idland, Michiyan
Hiverdale Ch~mical Co~pany
Chicd~o Heiqhts, Illinois
sodium salt
corporation~ subsidiary
Q-(2,4-Dichlorcphenoxy)
(2.'.-~ti)
R~loji,! Inc.
ChifJ:n.1tl Divi:5ion
butyric acid
(4-[2,4-DBJ)
:1.61'
-------
Portlal1d, Oregon
Rorcr-,\;r:cbem
Awchem ~~oJucts, Inc., division
Ambler, Pennsylvania
(Butoxone')
(Butyrac.)
2-(2,4-Dich1ocophenoxy) ethanol sulfate, sodium
salt (2,1~-lJichlocophenoxyethylsulfate, sodiu[!' salt)
(2.4-D::5) (Dlsul-soJ.ium)
GAl' Corporation
Chemical Division
LinJHn, New Jersey
2-(2.4-Dicblorophenoxy) propionic acid
Transvaal, Inc.
Jacksollville. Arkansas
(Crag herbicide 1')
0-2.4-Dichloroph~nyl O.O-diethyl phosphoro-
thioatc (O.O-Ciethy1 0-[ 2.4-dichlorophenyl]
Fbosphorothioate) (Nemacide)
~ohil oil Corporation
Mobil Cbemical Company. division
Industcial Chemicals Division
Charleston, South Carolina
(V-C13')
3-(3,4-Dichlocophenyl)-1.1-dimethylurea (DCr.U)
(Diuron) (DMU)
E. I. du Pont de Nemours & Company, Inc.
Biochemicals Department
La Porte. Texas
(Karr"ex I)
J-(J,4-Dichlorophenyl)-1-methoxy-1-methylurea
(Afalon) (Lilluron)
E. I. du Pont de Nemours & Company, Inc.
Biochemicals Department
La Porte. Texas
Industrial Chemicals Department
. East chicago. Indiana
2,4-Di~hloro~henyl-4-nitrophenyl ether
(!Iitrofen) (IILP)
Foh~ and HadS Company
PhiladeLphia, Pennsylvania
1,J:Dichloropropene
Dow Chemical U.S.A.
freeport. Texas
1, )- D ich 10 co p rop\~ne, 1. 2-d ic h loroprop ane
mixture (TC\lolle) (Vidden D)
Co~ (;1I0;n1--:,,1 11.S..~.
f(\.I\"port, 'T0xas
5:10.11 i..:n.'Inic.11 Co;n,>a.r¥
162.
(Lorax')
(Tok' )
(Telone ~)
(Dowf ume#NC)
-------
Industcial Ch~rnicals Division
DL'ec Park, Tex,~s
NOL"CO, Louisiana
(D-D#)
3, 4-Dich loropropiunanilide (Propanil)
Blue Spruce Company
~Jison, Sew Jersey
Rohm and 11.1.15 Curnpany
PhilaJelphia, Pennsylvania
Sobin Che~ical$, Inc.
Montroge Chemical Division
N~wdrk, New Jersey
(Stam')
2,2-Dichlocopropionic acid, sodium salt
DOli chemical U.S. L
r.idland, Michigan
(Dalapon')
4,4'-Uichloco-t-(trichloromethyl) benzhydrol
(Uicofol) (l,l-Bis (p-chlorophenyl]-2,2,2-
triChloroethanol)
Rohm and Haas Company
Philad~lphia, Pennsylvania
(Kel thane')
2,2-Dichlorovinyl dimethyl phosphate (DDVP)
(Dichlorvos) (U,O-Dimethyl-O-2,2-dichlorovinyl
Shell Cu~mical Company
Agricultural Division
Denver, Colocado
Mobile, Alabama
phosphate)
(Vapona')
Dieofol (See:
benzhyorol)
4,4'-Dichloro-'-(trichloromethyl)
a,O-DiethylO-(2-ehloro-i-[2,5-diehlorophenyl)
vinyl) phosphorothioJ. te (0-( 2-Chloro-1- (2, 5-
dichloropbenyl) vinyl) O,O-diethyl phosphoro-
thioate)
Shell chemical Company
A~ricultura1 Division
Denver, Colorado
(Akton'>
a,U-Diothyl Q-(3-chloro-4-methyl-2-oxo-2H-l-benzo-
pyriJ,n-7-y 1) phosphocothioa te (Coumaphos)
Daychem corporation
Chemaqro cocporation, division
Kansas City, Missouri
(Co-ra11)
o,a-Diethyl S-(p-ch1orophenylthiomethyl)
phosphoco1ithioatA (5-[ p-Chlcrophenylthio) methyl
O,O-diethyl pbosphocudilhioJ.te) (Carbuphenothion)
Stiluficc Chemicdl Company
A]ricultucdl chemicdl Division
-------
163
-------
Cold Creek, Aldbama
(Trithion')
O,O-Diethyl 0- (2, 4-tlichlorophenyl) phosphorothioate
(See: 0-2,4-Dichlorophcnyl O,O-diethyl phosphoro-
thioa te)
Diethyl-Jiphenyl-Jichloroethane (See:
bis (p-ethylpbtmyl) ethane)
1,1-Dichloro-2,2-
Diethyl dithiobis (thionoformate)
(Tr idcx)
?ike Chemicals, Inc.
Nitro, West Virginia
(Dexide)
(!:XD)
(lierbisant)
O,O-Diethyl S-(2-[ethylthio) ethyl) phosphoro-
dithioate (Disulfoton) (Dithiodemeton) (Dithiosystox)
(Thiodeincton)
8aychem corporation
che~aqro corporation, division
Kansas City, ~issouri
(Disyston')
C,O-DiethylO- (and S)-{2-[ethylthio] ethyl
phospborothioates (De~eton) (~ercaptopbos)
~aychem corporation
Chemagro Corporation, division
Kansas City, tlissouri
(Systox ')
O,O-Diethyl S-«(ethylthio] methyl)
ditbiodte (Phorate)
Av~rican Cyan~~id Company
Agricultural Division
Linden, Nell Jeesey
phosphoro-
(Thimet t)
O,O-DiethylO-(2-isopropyl-4-rnethyl-6-pyrimidinyl)
phosphorothioate
eiba-Geigy corporation
hgricultura~ Division
. ~crntosh, A1~bama
Prentiss Drug & Chemical Co., Inc.
New~rk, NCII Jersey
(Diazinon')
(Diazinon')
O,O-Diethyl O-tJ- (methylsulfinyl) phenyl
pho~phorothioate (Fensulfothion)
Bayehem corporation
Chernagro Corporation, division
Kansa~ City, Missouri
(Da.5ani tt)
0, a-Piet hyl 0- (p-n itroph eny 1) pJ.osphorothioa te
(O,C-Diethyl O-p-nitroph~n}'l t!lionoph("\sphate) (Ethyl
p..lL'ilthlon) (roll'iol) (Orth()pl~03) (P<.lLlthion)
(St~C' als[): o,U-LJi,~\,)t flY J 0-[ f'-nlt~Or:h'nyl ]r-hosphorothioat~)
~~0C1sallt 0 C().n[>~a)'
164
-------
Mons~nto Com~~rcial Products Company
Agricultu~al Division
Anlliston, Alabama
Stauffer Chemical Company
Agricultural Chemical Division
Mt. Pleasant, Tennessee
(Nirant)
O,O-Di~thyl O-(2-pyrazinyl)
(Thionazin)
Amorican cyanamid Company
Agricultuc~l Division
Linden, New Jersey
phosphorothioa te
(Zinophos')
N, :-:-Dietuyl-m-toluamiJe (DET) (DEET)
Chemical Formulators, Inc.
Chemical Divi:>ion
Nitro, -est Vir~inia
Hercule;o; IlIcol:[Jorated
Synthetics Departmcnt
3ruIl5.ic;k, Georgia
McLaughlin G0rmley King Company
~inneapolis, Minnesota
Pfiz\!r rne.
Chemicals Division
Greensboro, North Carolina
(l1etadelphenel)
O,O-Dict~yl-O-(3,5,6-trichloro-2-pyridyl)
thioate
Dow Chemical U.S.A.
Midland, Michigan
Fhosphoro-
.
Difolatanl (See: cis-N-( (1,1,2, 2-Tetrachloroethyl)
thio]-~-cyclohexene-1,2-dicarboximide)
2~3-DihyJro-2,2-dimethyl-7-benzofuranyl
methylcarbamate (Carbofuran)
FMC Corpora tion
Ch~mical Gr.oup
.Agricultural Chemical Division
MidJleport, New York
Industrial Chemical Division
Vancouver, Washington
(Puradant)
(Dihydroy\'n borJ.to) phenylmercury (See:
mercury borate)
Phenyl-
1,2-nihydro-3,6-pyridazinedione (See:
h y d r a :d rll! )
Maleic
J,5-uiiodo-4-hy~roxybenzonitrile
(58(' :
Ioy.ynil)
i,- (j -(l,O-D!t:';0f,c.JP:tlJithiopilosphor-ylpthyl)-
165
-------
b~nzene sulfona",ide (N-[ 2-l1ercaptoethyl]
benzcnl!$ultonamiJ0, S-[ O,O-(liisopropyl phosphoro-
dithiodt,~] .!;:;t'-'L-) (Dcnsulide)
Stautfer Chemical Company
Agricultural ~hemical Division
Cold Creek, AlaLama
(Betasan')
(Prefar ')
S-(O,O-UiisopLOpyl phosphocodithioate) ester
of 11- (2-lh~["cat'tocthyl) henzenesulfonamide
(Sae: N-[ ;-U,O-Diisopropylditbiophosphoryl-
ethyl]-lJenzene ::iulfonamiJe)
Dilan; (See: MixtULC containing
2-Uitro-l,l-bis [p-chlorophenyl]
2-Nitro-l,1-bis (p-chlorophenyl]
and 16~ related compounJs in 20i
butane (42.7~),
propane (21. J,; ]
xy lene)
Di:necron (See:
Phosphamidon)
Dimethoate (See: O,a-Dimethyl S-(U-methylcarbamoyl-
methyl] phosphorodithioate)
3-(Dimethoxyphosphinyloxy)-N,U-Jimp.thyl-cis-
crotonilmide (Ui~athyl phosphate of 3-hydroxy-N,N-
dimet h y l-c,is-croto namide) ()- Hyd rox y- N, /i-d imethy l-cis-
crotonamide-dimethyL phosphate)
Shell Ch<.)mical Company
Agricultural Division
Denver, colorado
(Bidr in.)
p-Dimethylaminobenzenpdiazosulfonic acid, sodium
salt (p-Dimethylamino benzene diazosodium sulfonate)
Baychem corporation
Chemagro corporation, division
Kansas City, Missouri
(Dexont)
m-( ( (Dimethy lamino) methy lene ]amino ]phenyl
methylcarbamate hydrochloride (Formetanate hyd~ochoride)
~or-Am Agricultural Products, Inc.
Chicago, Illinois
(CarzoU)
N-Dimethylamino succinamic acid
acid 2,2-dimethylhydrazide)
(Succinic
4-Dimethylamino-J,S-xylyl methylcarbamate
Dov Chemical U.S.A.
l1idl<1nd, Michigan
Dimethyl arsinic acid (See:
Cacodylic acid)
0, O-D im'.!lhy 1 0- (2-cdrbo,11cthoxy-l-methyl vinyl)
166
-------
phosphate (2-CdrboxY~8thoxy-1-~ethylvinyl
dimethyl ~hosrhate) (3-Hjdroxycrotonic acid, ~eth11
ester, di[11eth y 1 phosphd tc) (~et h y 1 3-
[di:netlloxyphos!Jhinyloxy) crotonate) (:1evinphos)
Shell ChelniCdl COI'l1'any
Agricultural Division
Denver, Colorado
(Phosdrin')
O,a-Dimethyl S-(p-chloro1'henylthio)
phosphorodithioate
Stdu(t~r Cnelnicdl Company
Agricultural Chemical Division
Coltl Creek, Alabama
rnethyl
(Methyl trithior
O,a-Dimethyl O-{1,2-dibrorno-2,2-dichloroethyl)
phosphat~ (Kaled) (1,2-Dibromo-2,2-dichloroethyl
dimethyl ~ho5phate)
standard Oil Company of California
Chevron Chcl:1ical Company, subsidiary
Ortho Division
Mdryland Heights, Missouri
Orlando, P'lorida
Richmond, Cdlifornia
South Pldinfield, New Jersey
O,O-Dimethyl-o-2,2-dichlorovinyl Fhosphate
(See: 2,2-Dichlorovinyl dimethyl Fhosphate)
O,O-DimethylO-p-{dimethylsulfamoyl)
phosphorothioate (Pam1'hur)
Americdll cyanamid Company
Agricultural Division
Linden, New Jersey
phenyl
(W arbex J)
Dimethyldithioc~rbamic acid, ferric salt
(Ferbam) (Ferde dimethyldithiocarbamate)
FMC Coc poc a t iL)n
Chemical Group
Agricultural Chemical Division
~iddleport, New York
Dirnethyldithiocarbamic acid, potassium salt
DimethyldithiocarbamiG acid, sodium salt
Dim~thyldithiocarhamic acid, zinc salt
O,O-D\.m,>tt,yl S-2- (l!thylsI11flnyl) "thyl phospboro-
Jithio.:tl' (():q\k;rh>toll~etb¥L) (5-2-[ ::thyls!llfinyl J
167
-------
ethyl o,O-methyl phosphorodithioate) (Cemzton-S-
rr.~t hy 1) (M'~t hy l-tl~mQton) (0-( 2- (Ethyl t!lio) ethyl)
O,o-di:r.ethyl phosphorothioat~)
6aychp~ co~poration
chem~gro corporation, division
Kan~a~ City, Missouri
(lleta-S ystox;)
O.O-Dimethyl-(1-hydroxy-2,2,2-trichloroethyl}
pho~phonate (Sea: O,O-Dimethyl 2,2,2-trichloro-l-
hydroxyethyl phosphonate)
O,O-Dimethyl S-(N-m~thylcarbaIToylmethyl)
phosphorodithiodte (Dimethoate)
Am~rican Cyanamid company
AgricuLtural Division
Linden, Nev Jersey
(cygon')
N,N-Dimcthyl-N'-(2-methyl-~-chloropbenyl)-
formamid i.ne (Chlorphenamldine) (Fundal)
Ciba-Geigy corporation
Agricultural Division
~clntosh, Alabama
Nor-Am Agricultural Products, Inc.
Chicago, Illinois
(Fundal')
O,O-Dimethyl O-(1-methyl-2-( l-pbenylcarbethoxy]
vinyl) phosphate. (Dimethyl phosphate of '-Methylbenzyl-
J-hydroxy-cis-crotonate)
Shell Chemical Company
Agricultural Division
Denver, Colurado
(Ciodrinl)
O,O-Dimethyl O-(4-(methyltbio]-m-tolyl)
phosphorothioi:l.te (F'enthion) (Lebaycid)
Baychem corporation
Chema~ro Corporation, division
Kansas City. Missouri
(Baytex I)
(Entext)
(Tiguvonl)
;1..68
-------
0, O-Dimet hyl 0- (p-ni tt"opheny 1) phosphot"oth loate
(O,O-Dimet.hyl O-p-nitt"opheny1 thiophosphate) (MPT)
(llcthy1 pdt"athion) (paduol)
Annual capacity
J~111i2D~_2I-f2~D~2L
I-'
()"\
I.D
Amf' ["icdn CYdrl..lmid Co:npany
Aqricul~urdl Uivision
Liwlen, ~'~\l J(.'c~ey
H.~r:calL'~; !ncccpocated
Synth8tic~ Uepart~cnt
Plaqu~min", Louisiana
KeL: c-Mc(;"\~ C0CpO ca tion
KC[l'-~!CI;e~ Ch'2.nir;al Cot"p., subsidiat"y
lI,i:niltc.'I, Mississippi (Mett"on')
Mons<.lllto Company
MonS,lnt 0 cOII\:T\l!t"cia1 Pt"oducts Company
,\,p:icultllL:
-------
dimethyl-ci$-crotonamide)
Cimetbyl Fho~Fh~te of 3-hydroxy-N-methyl-cis-
crotan~rnid~ (Sec: 3-Hydroxy-N-m~thyl-cis-
crotonamid~-dimcthyl phosphate)
Dimethyl Fhasphate of '-methylbenzyl-3-hydroxy-
cis-crotonatc (See: o,O-Dimethyl 0-( 1-metbyl-2-
(l-phcnylcarbl.!thoxy) vinyl] phosphate)
O,S-Dimethyl rhosphoramidothioate
aaychem corporation
Chcmagro cOLporation, division
Kansas city, ~issouri
Dimethyl phthalate
O,O-Dimethyl S-pbthalimidomethyl phosphoro-
dithioate (N-[Mercaptomethyl] phthalimide S-(O,O-dimethyl
phosphorodithioJ.te] ester) (Prolate)
Stauffer Chemical Company
Agricultural Chemical Division
Hend~rson, Nevada
(Imidant)
.;
Dimethyl tetr~chloroterephthalate (DCPA)
Diamond Shamrock Corporation
Diamond Shamrock Chemical Company
Ag['icultural Division
Gre~ns Bayou, Texas
(DacthaU)
3,S-Dimethyl-1,3,S-2H-tetrahydrotbiadiazine-2-
thionc (2-Thio-3,5-dimethyl-1,3,S-tetrahydro-
thialliazil1e) (DI1TT) (Dazomet)
II. A., Cleary cOLporation
New Brun$wick, ~ew Jersey
l1erck & Co., Inc.
Merck Chemical Division
, Hawthorne, lIev Jersey
Staritfer Chemical Company
,Specialty Ch~mical Division
Ardsley, Ne~ York
(Preservitt)
(BiocidetH 521)
O,07Dimethyl 2,2,2-trichloro-1-hydroxyethyl
phosphonate (Chlarphos) (Trichlorfon)
Baychem corporation
Chemagro Corporation, division
Kan$as City, Missouri
(Dipterext)
(Dylox~)
(Negu von#)
D b,~t h Y 1-1- (2,4, 'j- t rich lorophenyl) - 2-chlorov iny1
r h '" ~.; !J ~1 . \ t l~ ( 2 - C ill () r 0 - 1 - [ 2,:+, S - t t" i c h 1 0 !:' 0 P h ~ n y 1 ]
170
-------
vinyl dim~lhyl phosphat~)
Shell Chumical Co~prlny
Ag~~cultural Division
I\obil~, AlabaMa
(Gardona~)
O,O-Di~cthyl O-(2,~,5-lrichlorophenyl) phosphoro-
thioate (Dim~thyl 2,U,5-trichlorophenyl phosphoro-
th iQnate) p"enchlorfos) (Ronnel)
Dow Ch~mic~l U.S.A.
~idland, Michigan
(KOrlan ')
(Trolene:)
1, 1-Dimethyl-J- (I, I, '-trifluor:o-m-tolyl) urea
(J-[m-rrifluoromcthylphenyl]-1,1:dimethylurea)
(Pluometuron)
Ciba-Gei~y cor:poration
Agricultur:al Divi5ion
~cInto5h, Alabama
Hor:-Am Aq(icultur:al Products, Inc.
Chicago, Illinois
(Cotoran')
m-(3,3-Dimethylureido) ~henyl-tert-butylcartamate
F!1C I.:or:por:ation
Chemical Group
Agr:icultural Chemical Division
!1iddlepQrt, New York
4,6-Dinitro-o-sec-butylphenol (See:
Butyl-U,b-dinitrophenol)
2-sec-
Dinitrobutylphenol, ammonium salt
Dow Chemical U.S.A.
Midland, Michigan
2,4-Dinitro-6-sec-butylphenyl isopropylcarbonate
(See: Dinobuton)
Dinitrocaprylphenyl crotonate (2-[1-~ethylheptyl]-
4,6-dinitr:ophcnyl crolonate)
Rohm dnd Haas Company
Bristol, Pennsylvania
PhilaJelphia, Pennsylvania
(Iiara th ane ')
4, 6:'D1ni tro-o-cresol (DNC)
Blue Spruce Company
Edison, New Jersey
(DNaC)
~,o-Dinitro-o-cresol, sodium salt (2-Met.hyl-~,6-
dinitrophenol, sodiu~ salt)
Blue Spruce company
rldi~vn, New Jersey
171
-------
2.6-DinitLo-N.N-dipropyl-p-toluidine
Eli Lilly dn1 Conpany
Tippecanoe L~bordtorics
~df~yette. Indiana
ij.6-Dinitrophenol-o-sec-butylphenol (See:
ij.6-Jinitrophcnol)
2-sec-Butyl-
2.4'-Dinitro-4-trifluoromethyldiphenyl ether
Ciba-Gciqy corporation
A~ricultural Division
i'lcIntosh. Alabama
(Preforanl)
Dinobuton (2-sec-Butyl-4.6-dinitrophenyl isopropyl
carbona tel (2. ij-DinitLo- 6-scc-bu ty I phcn yl isopropyl
cdLbonate) .
Union Carbid~ corporation
Chemicals anJ Plastics Division
Institut~ and South" Charlest (Dessin')
Dinoseb .(See:
2-sec-autyl-ij.6-dinitrophenol)
p-Dioxane-2,J-diyl ethyl phos;>horodithioate (2.3-p-
Dioxane-S,S-bis [O,O-diethylpho~phorodithioate])
(2,J-p-Dioxanedithiol S,S-bis (O,O-dietbyl phosphoro-
ditnioate D (Dioxdnthion)
Hercules Incorporated
Synthetics Department
HattiesDurq, Nississippi
(Delnav I)
Dioxanthion (Sec: p-Dioxane-2,3-diyl ethyl
phosphorodithioate)
Dipterext (See: O,O-Dinethyl 2,2,2-trichloro-1-
hydroxycthyl phosphonate)
Diphacinone (S~~e:
2-Diphcnylacetyl-1,3-indandione)
Diphenylacetonitrile)
Diphenatrile (See:
Diphenyl (See:
Biphenyl)
Dip~cnylacetonitrile (Diphenatrile) (Diphenyl-'-
cy anomet ni:lne) (Dip heny lme t hy lcya nide) (1- Phenyl benzylcyanide)
Ashland Oil. Inc.
Ashland Chemical Company, division
Chemical Products Division'
Gr~3t M~udows, New Jersey
Eli Lilly and Company
Tipl"~<:.1.noe Laboratot"ies
L d t.1 Y '-' t t e . r nd icl n ~
172 '
-------
2-~irhenylacetyl-1,3-indandione-1-hydrazone
(D i p h.-I C i no n..}
N~asc Chemical Company, Inc.
Stdte college, Pennsylvania
Dip hen y I J. In in e
DiphenylmercuriBmmonium propionate
!'!t!rCK & Co., Illc.
Merck Chemical Division
Hawthorne. New Jersey
Di(phenylmetcury)dodecenyl succinate
Tenneco Inc.
Tenneco Chemicals, Inc.
Interme~iates Division
Elizabeth, New Jersey
Long ~each, california
(Super AJit)
Di-n-propyl isocinchomeronate
McLaughlin Gormley King Company
Minncapolis, Minnesota
Di-n-propyl 6,7-methylenedioxy-3-methyl-1,2,3.4-
tetrahydronaphthal~ne-1,2-dicarboxyldte (Di-n-
propylmaleatc isusafrole condensate) (n-Propyl isome)
CPC International, Inc.
S. B. Penick & Company, division
Xontville, New Jersey
Disodium methane arsonate
acid. disodium salt)
(Sec:
l'1ethanearsonic
Disodium methyl arsonate (See:
acid, disodium salt)
Methanearsonic
,
Disul-sodium (See: 2-[2,4-Dichlorophenoxy] ethanol
sulfate, sodium salt)
Disulfaton (See: O,O-Diethyl 5-(2-
(ethy lth io) ethyl] phosphorodithioa tel
Di-syston'l (See: O,O-Diethyl S-[ 2-
(etbylthio) ethyl] phosphorodithiuate)
Dithane1t (See: Ethylene bis [dithio-
carbamic acid], salts)
Dit~liobil; ttaiocarbonyl i;r.inoethylene
carlJ..1;I:ic i1ci..l, zinc salt (Polyra!T)
H~ ceo r po r i\ t ion
Chp~~ ico'l 1 Gro'Ji)
bis dithio-
173
-------
Agricultural Chemical Division
~iddl~port, New YorK
(Polyran")
Dithiodpmeton (See: O,O-Diethyl S-[2-(~thylthio)
ethyl] pho~phorodithioate)
Dil:hioslstox (S~~:
phosphorodithioate)
O,O-Diethyl S-(2-(ethylthio) ethyl]
Diuron (SeE':
ditT1(!t hy lurea.)
J-[J,4-Dichlorophenyl]-1,1-
Douecachloro-octahydro-1,J,4-metheno-2H-
cyclobuta [cd] pentalene (/'Iirex) (Perchloropenta-
cyclodecane)
Occidental retcoleum corporation
Hooker chemical Corporation, subsidiary
Electroc~emical and Specialties Divisions
Nia~ara Falls, New York (Dechlordn~')
Dod~cylquanidine acetate (Dodine)
American CYdnamid Company
Agricultural Division
Linden, New Jersey
(cyprex ')
Dodecylgua.nidine hydrochloride
American Cyanamid Company
Industrial Chemicals and Plastics Division
Linden, Nev Jersey
Dodine (See:
Dodecylguanidine acetate)
Drinox H-J4 (See:
Heptachlor)
DuphaL"' (Se~:
sulfone)
p-Chlorophenyl 2,4,S-trichlorophenyl
Dybar~ (See:
1,1-Dimethyl-J-phenylurea)
Dyfonate' (See:
dithioate)
O-Ethyl-S-phenylethylphosphono-
Dy19X' (See: O,O-Dimethyl 2,2,2-trichloro-l-
hydroxyethyl phospnonate)
.Dyrenel: (See:
triazine)
2,4-Dichloro-6-[o-chl~roaniline]-s-
EDt! (Se~!:
1,2-Dibromoethane)
iDe (:;ce:
Ethylnne dichloride)
174
-------
EGT (See:
Ethlleneglycol bis (t~ichlo~oacetate])
EPN- (S~e: a-Cthyl a-(p-nit~ophenylJ phenyl
pho~phonothioate)
~PTC (See:
S-Ethyl N,N-di-n-propylthiocar~a~ate)
EXU (See:
Dicthyl dithiobis (thionoformate)
lmmi# (See: N-Ethylmercuri-l,2,3,6-tetrabydro-3,6-
cndomethanc-3,4,5,6,7,7-hexachloropbthalimide)
Endo$ulfan (See: 6,7,8,9,10,10-Hexachloro-
1,5,Sa,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxanthiopin-
3-uxiJe)
Endothall (See: 7-0xabicyclo (2.2.1) heptane-2,3-
dicarboxylic acid, disodium salt)
tn~rin (1,2,3,4,10,10-Hexachloro-6,7-epoxy-
1,4,4',5,6,7,8,8'-octahydro-l,4-endo,endo-5,S-
dimethanonaphthalcne)
Northwe~t Industries, Inc.
Velsicol Chemical corporation, subsidiary
Memphis, Tennessee
Entexl (See: U,O-Dimethyl-0-(4-(methylthio)-m-tolyl)
~hosphorothioate)
Eptamt (See:
S-Ethyl N,N-di-n-propylthiocarbamate)
Er~on (See: 2-(2,4,S-Trichlorophenoxy] ethyl 2,2-
dichloropropionate)
Ethion (0,0,0' ,O'-T~traetb.yl S, S '-methylene bis-
phosphorodithioate)
fMC corporation
Ch~Inica 1 Group
'Industrial Chemical Division
Baltimo~e, Maryland
Ethohexadiol (See:
2-Ethyl-l,J-hexanediol)
~th~xy~uin (6-Ethoxy-l,2-dihydro-2,2,4-trimethyl-
qu ino 1 ine)
:1onsanto Company
Monsanto ComIilercial Products Company
Aqricultulal Division
Nitro, West Virginia
(Santoquint Liquids)
Ethrcl~
(St'>:! :
2-Chloro~thyl Fhosphonic acid)
175
-------
2-(fthyldmino)-4-(i50propylamino)-6-~et~oxy-s-
trL.17. ine (Atra trone) (Gesa tar. in)
Ciba-Ceiqy ~urporation
A~ricultural Division
Mcrntosh, Alabama
2-ithylamino-4-isopropylamino-6-methyl-s-triazine
Cibd-G~iqy corporation
Agricultural Division
Mclnto~h. Alabama
(EvikTIU)
S-Ethyl cyclohexylethylthiocarbamate (See:
N-cthyl-N-cyc10hexylthiocarbamate)
S-Ethyl
Ethyl 4,4'-dichlorobenzilate
Ciba-Geigy corporation
Agricultural Division
aclntosh, Alabama
(Chlorobenzilate)
S-Ethyl diisobutylthiocarbamate (Butylate)
Stauffer Chemical Company
Agricultural Chemical Division
Cold Creuk. Alabama'
(Sutan')
O-Ethyl S,S-dipropyl phosphorodithioate
Mobil Oil corporation.
Mobil Che~ical Company, division
Industrial Chemicals Division
"to Pleasant. Tennessee
(Prophos)
("oeap' )
S-Ethyl N,N-di-n-propylthiocarbdmate
Stauffer Chemical Company
Agriculturdl Chemical Division
. Cold Creek, Alabama
(EPTC)
(Eptamt)
Ethyl ene
Ethylene aldehyde (See:
Acrolein)
Ethylene bis (dithiocarbamic
salt (Amobam)
Blue Spruce company
, Edison, New Jersey
Fixe Chemical~, Inc.
Nitro, West Virginia
acid). diarnmonium
Ethylene bis (uithiocarbamic acid). disodium salt
(Disodium ethylene bis dithiocarb
-------
Nitro, West Virginia
FI1C CoqJoration
Chc:nic-ll Group
Agricultural Chemical Division
lIid(lleport, Neil York
Rohm and Haas Company
PbilaJclphia, Pennsylvania
(DithaneJ)
Ethylene his (dithiocarbamic acid), manganese salt
(11aneb) (:-lED)
Blue Spruc8 Company
EJison, New Jersey
E. I. du Pont de Nemours & Company, Inc.
Siochemicals De?artment
La Porte, Texas
Rohm and "a as Compani
Philadelphia, Pennsylvania
(11 anza t e t)
(Dithane#)
Ethylene bis (dithiocarba~ic acid), zinc salt (Zineb)
(Parazate)
Blue Spruce Company
Edison, New Jersey
PMC Corpocation
Chemical Group
Agricultural Chemical Division
l1iddleport, New York
Pennwalt corporation
Chemical Division
Wyandott~, Michigan
Bohm and "ad9 Company
Philadelphia, Pennsylvania
(Dithanet)
Ethylp.ne dibromide
Ethylene dichloride
Etbyl~ne glycol bis (trichloroacetate) (EG!)
Occidental Petroleum Corporation
Hook~r Chemical corporation, subsidiary
Electroche~ical and Specialties Divisions
Niagara Palls, New York (Glytac#)
Eti1ylene oxide
S-Ethyl N-ethyl-N-cyclohexylthiocarbamate
(S-Ethyl cyclohexylethylthiocarbamate) (Cycloate)
Stauffer Chemical Company.
Agricultural chemical Division
Cold C=eek, Alacama
(Ro-neet ')
Ethyl formatp
177
-------
S-Ethyl hexahydro-1H-azepine carbothioate (Ethyl
1-hcxamethylcne imine carbothiolalate) (Molinat~)
Stauttcr Ch~~ical Company
Agricultural Chemical Division
Cold Creek. Alaba~a
(Ordramt)
2- Eth Y 1-1. J- h exancdiol (Ethohexad iol) (2-E th y1-3-
propyl-1.3-propanediol)
Union Carbide corporation
Chemicals and Plastics Division
Institute and South Charleston. West Virginia
N- (2-f.thylhexyl) bicyclo- (2.2.1) -S-l1eptene-2.3-
dicar boxilnide (N-Oct y 1 bicyc lohep tened icar box imide)
(Octacide 2b4)
McLaughlin Gormley King Company
Minneapolis. ~innesota
(liGU 264)
Ethylmercury chloride (Chloroethylmercury)
mercuric chloride)
Eli Lilly and Company
Tippecanoe Laboratories
Lafayette. Indiana
(Ethyl
Ethyl methylene.phosphorodithioate (See:
Et hion)
Ethyl 4-(mHthylthio)-m-tolyl isopropylphosphoramidate
Baychem Corporation
Chemagro corporation. division
Kansas City. Missouri
Ethyl parathion (See:
phosphorothioate)
O.O-Diethyl O-(p-nitrophenyl)
. .
O-Ethyl-S-phenyl-ethylphosphon~dithioate'
Stauffer Chemir.a1 Company
Agricultural Chemical Division
cold Creek. Alabama
2-Ethyl-3-propy1-1,3-propanedi~1 (See:
hexancdiol)
2-Ethyl-1,3-
Ethyl pyrophosp~ate (Tetraethyl pyrophosphate)
(TEPl') .
Aleo S~dndard Corporation
Miller Chemical and fertilizer Corporation.
Hanover, Pennsylvania
subsidiary
S-2-(EthyI3ulfinyl) ethyl 0, a-dimethyl phosphoro-
thio3tc (See: O,U-Cimethyl S-2-(ethylsuliinyl) ethyl
Fhospho~o~ithiodtc)
U8
-------
0-( '2- (::thyltilio) ethyl J O,a-dimethyl phosphorothioat~
(S~P: a.a-Dim~thyl S-2-(cthylsulfinyl] ethyl p~osphoro.
di thiod tel
Ethyl ~anthogcn disulfide
Pike Chemicals. Inc.
Nitro, West Virginia
Fa:l1;J:tu;: (See: O,O-Dimethyl O-p-[ dimethylsulfamoyl]
phenyl Fho$phorothioate)
Fe;tac, (See:
(2,3,6-Trichlorophenyl] acetic acid)
Fenchlorfos (See: O,a-Dimethyl O-(2,4,5~trichloro-
ph~nyl] phosphorothioate)
Fel1opr;op (See:
propionic acid)
2-(2,Q.S-rrichlorophenoxy]
fensulfothion (See: O,O-Diethyl O-p-[methylsulfinyl]
phenyl phosphorothioate)
Fenthion (See: O.O-Dimethyl O-[4-(methylthio)-m-tolyl]
Fhosphorothioate)
Fenuron TCA (See:
trichloroacetate)
1.1-Dimethyl-3-phenyluroa
Ferbam (See: Dimethyldithiocarbamic
acid. ferric salt)
Fer1Jerk# (See:
ferric salt)
Dimethyldithiocarba~ic acid,
Fluometuron (See: 1,1-Dimethylurea-3-['",I-
trifluoro-m-tolyl] urea)
Folex' (See:
Tributyl phosphorotrithioite)
Folpet (See:
. .
N-(Trichloromethylthio] phthalimide)
Fonnalrlehyde
Formalin (See:
Formaldehyde)
Fonr.etilnate hydrochloride (See: m-( ([ Dimethylamino]-
mcthylene)aminoJ phenyl met~yl carbamate hydrochloride)
Fruitone
(Se e:
p-ChlorophenoxyacAtic acid)
F' u ~. ~ l! ~ i n
(:5 oJ e:
Dimethyldithiocarba~ic acid, zinc salt)
179
-------
Fundal (See: U,N-Dimethyl-N'-[2-methyl-~-cbloro-
phenyl] formamidine)
Fur4dan~ (See: 2,3-Dihydro-2,2-dimethyl-7-bcnzo-
fur~nyl methylcarbamate)
J-(1-Furyl-3-a~etylethyl)-ij-hydroxycoumarin
(3-( ;-Acetonylfurfuryl ]-4-hydroxycoulTarin)
(Coum4turyl)
itorer-Amchem
A~cbem Products, Inc., division
Ambl~r, Pennsylvania
Fremont, california
St. Joseph, Missouri
Gardo na t (See: Dimethyl-1-[ 2, ij, 5-trichlorophenyl ]-
2-chlorovinyl phosphate)
Genite. 923 (See:
benzenesulfonate)
2,4-Dicblorophenyl
Gesaqard (See:
s-triazine)
2,4-8is [isopropylamino )-6-methyl thio-
Gibterellic acid. (Gibberellin)
Abbott Laboratories
Agricultural/Veterinary Products
North chicago, Illinois
Merck & Co., Inc.
Merck Chemic~l Division
Danville, Pennsylvania
Division
(Pro-Gibbt)
Glyodin (2-Heptadecyl-2-imidazoline)
Union Carbide corporation
Chemicals dnd Plastics Division
.' Institute and South Charleston,
!lest Virginia
Glytac. (See:
Ethylene glycol bis [trichloroacetate)
Goodrite Z.I.P. (See:
zin!= salt)
Dimethyldithiocarba~ic acid.
Gophacide' (See: 0,0-8is [p-chlorophenyl]
dcetimidoylphosphoramidothioate)
Guthion4 (See: O,a-Dimethyl. s-[4-oxo-1.2,3-
benzotrialin-J-(4H)-ylmethyl] phosphorodithioate)
HC.' (:;0C:
!I~ x
-------
Hca {S0e:
Hexdchlorobenzen~
Heptachlor (1,4,5,6,7,8,8_-Heptachlorodicyclopenta-
diene) (1,4,5,6,7,8,8-Heptachloro-J.,4,7,7.-tetrahydro-
4,7-~cthan~ind~ne) (Heptachloro-tetrahydro-endo-
methdnoinienf'!) (Drinox H-J4)
I!o=-thwe~t Illdustries, Inc.
Velsicol Ch<:>lnical corporation, subsidiary
~~mphi~, Tennessee
2-~eptdaecyl-2-imidazoline (See:
Glyodin)
HerDant (See: 3-[ Hexahydro-4. 7-rr:ethanoindan-S-
yll-1.1-dimethylurea)
Herbisan' (See:
Diethyl dithiobis [thionoformate])
HeXdc hloroace tone (HC A) (Hexachloro-2-prop anone)
Allied Chemical corporation
Specialty Chemicals Division
Baton Rouge. Louisiana
Hexachlorobenz
-------
dimcthdnonaphlhalene
(S ce:
Endrin)
Hexdchloro-~poxy-octahydro-endo, exomethano-
naphthal~ne (See: Dieldrin)
U~xachloro-h~xahydro-cndo-exo-di~ethano-
naphthalene (See: Aldrin)
6,7,!;,9,1\J,10-lIo;!xachloro-1,5,5a,6,9,9a-hexahydro-
6,~-mBthano-2,4,J-benzodioxanthiepin-J-oxide
("-1,2,J,4,7,7-Hexachlorobicyclo (2.2.1]-hepten-
5,r.-bi::ioxy:nethylo?ne sulfite) (1,4,5,6,7, 7-Hexachloro-
5-norbornene-2,3-dimethanol, cyclic sulfite)
(Endosulidn)
F~C ~orpocation
Chcmical Group
A~ricultural chemical Division
~iddlcport, Nev York
(THadan.)
Hexachlaro-2-propanone (See:
Hexachloroacetone)
Hormodin' (See:
Indole-J-butyric acid)
Hydrogen cyanide
Hydrotbal (See:. 7-0xabicyclo.( 2. 2.1] heptane-2,3-
dicarboxylic acid)
2-Hydroxybiphenyl (See:
0- P heny lphenol)
3-Hydroxycrotonic acid, methyl ester, dimethyl
phosphate (See: O,O-Dimethyl O-(2-carbomethoxy-
1-methylvinyl) phosphate)
Hydroxydimethylarsine oxide (See:. Cacodylic acid)
J-~ydroxy-N,N-dimethyl-cis-crotonamide-
dimethyl Fhosphate (See: J-(Dimethoxyphosphinyloxy)-
N,N-dimethyl-ci~-crotonamide)
2-Hydroxyethyl-n-octylsulfide (Repellent 874)
McLaughlin Gormley King Company
. Minneapolis, Minnesota
(Hydroxy:nercuri) benzene (See:
Phenylmercury hydroxide)
3-Hydroxy-N-methyl-cis-crotonamide-dimethyl-
fhosphat.!
$hell "':h~rnical COlflpany
h~ricultural Division
D?n vcr, Col')rildo
. (AzotlrinJ)
182
-------
N-Uydroxynaphthalimide diethyl phosphate
Bayche~ corporation
Ch~m~gro cor~oration, division
~ansas city. ~issouri
Hydroxy~henylmercury (See:
Phenylmercury hydroxide)
2-ay.Jroxyprupyl methanethiolsulfonate
duckman Laboratories. Inc.
Cadet, Missouri
"emphis, Tennessee
a-Hydroxyquinoline, copper salt (See:
coppe r sa It)
a-Quinolinol,
ElYViH' (See:
5-Bromo-3-sec-butyl-6-methyluracil)
IPC (See:
Isopropyl N-phenylcarbamate)
Iqran 80~' (See: 2-tert-Butylamino-4-ethylarnino-6-
methylthio-s-triazine)
lmidan' (See: o,O-Dimethyl S-phthalimidomethyl
phosphorodithioate)
Indalone' (See:
Butyl mesityl oxide o~alate)
lndole-3-butyric acid (4-(3-In101y1]
Syntcx corporation .
Arapahoe Chemicals Division
Doulder, Colorado
butyric acid)
loxynil (3,5-Diiodo-4-hydroxybenzonitri1e)
Rorcr-Al1'chem
Amchem Products, Inc., division
Fremont, California
Isobornyl thiocyanoacetate (Terpinyl thiocyan~
acetate) (Thanite)
Blue Spruce Company
Edison, Ncw Jersey
Hercules rncorporat~d
Synthetics Department
. Brunswick, Georgia
McLaughlin Gormley King Company
Minneapolis, Minnesota
I soci 1
(Se~:
5-0~omo-3-sec-but¥I-6-methyluracil)
0- r~;Opl'O pox y ph
-------
Chema~ro ~orporation, division
Kaosa$ city. Missouri
(Baygon I)
Isopropyl carbanilate (See:
carbamate)
Isopropyl N-phenyl-
Isopropyl 3-chlorocarbanilate (3-Chlorocarbanilic
acid, isopropyl ester) (Isopropyl N-[ 3-chlorophenyl J
ca.rbamate) (Chloro-IPC) (Chloropropham) (CrFC)
PPG InJu~tries, Inc.
Chemic~l Uivision
Industrial Chemical Division
Barberton, Ohio
Isopropyl N-(J-chlorophenyl) carbamate (See:
Isopropyl J-chlorocarbanilate)
Isopropyl 4,4'-dichlorobenzilate
~iba-Geigy corporation
Agricultural Division
McIntosh, Alabama
(Acaralatet)
Isopropyl N-pbenylcarbamate (Isopropyl carbanilate)
(IPC) (I?ropham)
PPG Industries, Inc.
Chemic~l Divizion
Industrial Chemical Division
Barberlon, Ohio
KOCN (See:
Potassium cyanate)
Kaizate4 T.P. 6 (See: (2,4,S-Trichlorophenoxy]-
propionic acid. potassium salt)
KaratbaneJ (See:
Dinitrocaprylphenyl crotonate)
Karbutildte (See:
bu tyl~q.rbdma te)
m-(J,J-Dimethylureido]phenyl-tert-
Karmex' (See:
dimcthylured)
J-( 3, 4-Dichlorophenyl ]-1, 1-
Kel~hane (See:
benzbydrol)
4,4'-Dichloro-'-(trichlorome~hyl]
Keponei (See: Decachloro-octahydro-1,3,4-metheno-
2il-cyclobuta [CD) pentalen-2-one)
Kloben# (S~~:
butylurp<.l)
3-( j,~-Dichlorophcnyl)-1-methyl-1-n-
KorlJ.l)J (SPot!:
O,O-DimethylO-(2,4,S-trichloro-
184
-------
ph~nyl) Fhosphorothioate)
(Lactoyloxy) phenylmercury (See:
lacta te)
Phenylmercury
Landrint (See:
2,3,S-Trimethylphenyl metbylcarbamate)
L,Ulndte. (See: S-l1ethyl N-( (methylcarbamoyl) uxy)
th ioac\~ t i m i<1 ate)
Lam;tan' (See:
1-Cbloro-2-nitropr6pane)
Las500 (See: 2-Chloro-2,6' diethyl-N-
(mcthoxymethyl) acetanilide)
Lead a:senate (Plumbous arsenate)
Chempar Chemical Co., Inc.
Portland, Oregon
Dimensional Pigments, Inc.
Bayonno, New Jersey
FMC Corporation
Chemical G.coup
Agricultural Chemical Division
Middlcport, New York
Los Angeles ~hemical Company
South Gate, California
Somerset Tir~ Co.
30unJ BrooK, New Jersey
Standard Oil Company of California
CheVLon chemical Company, subsidiary
Or tho Division
Ricbmood, California
Leba ycid (See: 0, O-Di~lethy 1 0-[ 4- (metbylthio)-m-
tolyl) Fhosphorothioate)
Leptophos (See: 0-[ 4-Uromo-2,5-dichlorophenyl )-0-
methyl. ph.enylphosphorothioate)
Let h a n e 384 (S ce :
thiocyana tel
2-[2-Butoxycthoxy) ethyl
Lins]ane
hexane,
(See: 1,2,3, 4, 5,6-Hexachlorocyclo-
1 OO~ i-isomer)
Linuron
methoxy,
(See: 3-( 3,4-Dic"hlorophcnyl)-1-
1-methylurea)
Liquiphene# (Sec:
Phenylmcrcury acetate)
!.ir.ha.t.,~ 2,~-D (Se~: C 2,4-Cichlor:ophEmoxy J
de..!ti..:: dci,j, lithium salt)
185
-------
Lithat~' 2,~,5-T (See: (2,4,5-Trichlorophenoxy]
acetic acid, lithium salt)
Litbate' 2,~,5-Tr (See: [2,4,5-Trichloropher.oxyJ-
propionic acid, lithium salt)
Lorox I (See: )-( 3, 4-Dichlorophenyl )-1-
methoxy, 1-m~thylurea)
r.C£' (See:
IIC!?A (See':
(~-Chloro-o-tolyloxy] acetic acid)
(4-Chloro-o-tolyloxy] acetic acid)
MCPB (See: 4-(2-lIethyl-4-chlorophenoxy]
butyric acid)
IIGK 264t (See: N-( 2-Ethylhexyl] bicyclo-( 2.2.1 ]-5-
heptene-2,3-dicarboximide)
l!H (See:
"alcic hydrazide)
"SMA (S~e:
lIethanearsonic acid, ~onosodium salt)
~alachite green (See:
Copper carbonate)
Malatbion (S-[1,2-Bi5 (ethoxycarbonyi) ethyl) 0,0-
dimethyl pho5pborodithioate) (S-(1,2-Dicarhethoxy-
ethyl] D,O-dimethyl dithiophosphate) (Mercapto-
succinic acid, diethyl ester, D,a-dimethyl dithio-
~hosphate)
Americ3n Cyanamid Company
Agricultural Division
" Linden, New Jersey
Blue Spruc~ Company
Edison, New Jersey
Prentiss Drug & Chemical Co., Inc.
.' Newark, New Jersey
r.aleic hydrazide (1,2-Dihydro-3,6-pyridazinedione)
The Ansul Company
Chpmical Division
Marinette, Wisconsin
Chemical Formulators, Inc.
Chemical Division
Nitro, West Virginia
Pairmount Ch~mical Co., Inc.
Newark, New Jersey
(Sucker-St ufO)
~dll~h (S(!a: Ethylene bis (dithio.:arbamic acid],
n:a 1I'1d !lPS..:o ~d 1 t)
186
-------
Marlate' (See:
phenyl] ethane)
'.'.1-Trichloro-2.2-bis (p-rnetboxy-
I'!atacil# (Se~: 4-( Dir!1ethylamino ]-rn-tolyl
methy lcar:bdmd tel
Memmi' (See: N-(Metnylrnercuri]-1.4.5.6,7.7-hexa-
chlor:obicyclo (2.2.1] hept-S-ene-2.3-dicar:Loxirnide)
2-~cr:cdptobcnzothiazole. zi~c salt (Zinc ~8T)
Amerlcan cyanamid Company
Oryanic Chemicals Division
Bound Brook. New Jersey
E. I. du Pont de Nemours & Company. Inc.
Elastomer Ch~rnicals Department
De~pvater: Point. New Jersey
The B. F. Goodrich Company
B. F. Goodrich Chemical Company. division
Henry. Illinois
The Goodyear: Tire & Rubber Company
Chemical Division
Niagara Falls. New York
N-(2-~ercaptoethyl) benzenesulfonamide-S-(O,O-
diisopropy 1 phosphorod i thioa tel ester
(See: N-('-O.O-Uiisopropyldithiophosphorylethyl]
benzene sUlfonamide)
N-(Mer:captomethyl) phthalimide S-(O.O-dimethyl
pho:.>phorodithioate) ester (See: O,O-Dimethyl S-
phthalimidomethyl phosphor:odithioate)
~ercaptophos (See: O.O-Diethyl 0 (and 5J - (2-
(ethyltbio) ethyl] phosphorothioates)
Mercaptosuccinic acid. diethyl ester. a.a-dimethyl
dithiopbosphate (See: Malathion)
Mcrcu~ial turf tungicides
Mallinckrodt Ch~mical Works
Industrial Chemicals Division
St. Louis. Missouri
Mercuric chloride (See:
Mercury bichloride)
I'Ictadelphene# (See:
N.N-Diethyl-m-toluamide)
M'~la-Systox~ (Sec: O.O-DirT"~thyl S-2-
[cthyl~ulfinylJ ~thyl phos?horodithioate)
:-\et~m (:;~t.~:
/;-i'\0.thyl,lithioc..Icbdrric acid, sodium salt)
187
-------
~etham (Sec:
salt)
N-~ethyldithiocarba~ic acid, sodium
Methanearsonic acid, calcium acid salt (Calcium
acid m~thyl arsonate)
MethanCdrsanic acid, disodium salt (DSMA)
(:1ethar) (Disodium methane arsonate) (I;)isodium
m~thyl dr~onate) .
Th~ Ansul Company
Chemical Division
Marinette, Wisconsin
w. A. cleary corporation
New Brunswick, Nev Jersey
Diamond Shdm~ock corporation
Diamond Shamrock Chemical Co~pany
Agricultural Division
Greens Bayou, Texas
r.ethanearsonic acid, doaecyl- and octyl-ammonium salts
~. A. Cleary corporation
Nev Brunswick, Nev Jersey
(Ansar' 184,8100)
Methanear30nic dcid, monosodi~m salt (MSMA)
(~onosoJium methyl arsonate)
The Ansul Company
Chemical Division
3arinctte, Wisconsin
Diamond Shamrock corporation
Diamond Shamrock Chemical Company
Agricultural Division
Gr~ens Bayou, Texas
(Ansar' 170 H.C., 529 H.C.)
l'Iethazate (See:
sa it)
Mcthomyl (See: S-Mcthyl N-( (methylcarbamoyl) oX11
th ioacct imiJa te)
Dimethyldithiocarba~ic acid, zinc
2-~ethoxy-4.b-bis (isopropyldmino)-s-triazine
(PI:?metone). .
eiba-Geigy corporation
Agricultural Division
McIntosh, Alabama
(pramitoU)
M~thoxychlur (S~e: 1,1.1-Tl:ic~loro-2,2-bis (p-
mcthoxyphl!nyl] ethane)
Metht:::f DOT (S(!e: 1,1,1-Trichlol:o-2,2-bis (p-
mctauxi'i'hpl~yl] ethdll(')
188
-------
r.ethyl bro~idc (See:
Bromomethane)
r.ethl1-1-(butylcarbamoyl)-2-benzimidazole
carba:T1ate
~. I. du Pont de Nemours & Company, Inc.
Biochemicals Department
Belle, West Virginia
(Benlatel)
2-~ethyl-4-chlorophenoxyacetic acid (See:
C~loro-o-tolyloxy] acetic acid)
4-(2-11ethyl-4-chlorophenoxy) butyric
sodium salt (Cantrol)
Rorer-A~chem .
Amcbem Products, Inc., division
Ambler, Pennsylvania
Fremont, California
St. Joseph, Missouri
acid
(2-(2-11ethyl-4-chlorophenoxy]propionic acid)
PSI-Gorden Corporation
~ansas city, Kansas
( 4-
~ethyl-demeton (See: O,O~Dimethyl S-2-(ethylsulfinyl]
ethyl phosphorodithioate)
~ethyl 3-(dimethoxyphosphinyloxy) crotonate
(See: 0, a-Dimethyl 0-[ 2-carbomethoxy-l-
methylvinyl] phosphate)
2-11etbyl-4,6-dinitrophenol, sodium salt (see:
Dinitro-o-cresol, sodium salt)
4,6-
potassium sal t (Basan')
N-l1ethyldithiocarbamic acid,
5uckmdn Laboratories, Inc.
Cddet, l1issouri
aemphis, Tennessee
N-~ethyldithiocarbamic acid, sodium salt
(I'.etam) (f1etham) (SMDC) (VPM)
Chemical Formulators, Inc.
Chemical Division
, Nitro, Wcst Virginia
E. I. du Pont de Nemours & Company, Inc.
Biochemicals Department
La Porte, Texas
Stauffer Chemical Company
Agricultural Chemical Division
Ardsl~y, New York
Richmond, Cdlifccnia
(Vapam' )
(Vapc.I"')
Methyll!l\~bL; thiocy.\lIiltf!
189
-------
American Cyanamid Company
rn~ustri31 Chemicals and
LiI1\1('c:, Ne'rl Jersey
Bucf.mdn Labor
-------
Che~ica15 and Plastics Division
Institute and South CharIest (T€~ikt)
~ethyl na~ate (See: Dimethyldithiocarba~ic acid,
sodium salt under Rubber Processing Che~icals)
Melhyl p~rathion (See:
Fhosphorothioate)
o,O-Dimethyl o-[p-nitrophenyl]
~ethylphosphoramidic acid, 4-tert-butyl-2-chloro-
phenyl methyl ester (See: u-tert-Sutyl-2-chloropaenyl
~et~yl methylphosphoramidatc)
3- (2- Methy 1 p iperid ino) propy 1-3, 4-dichloro1:enzoate
(Piperalin) .
~li 1illy and Company
Tippec~noe Laboratories
Lafayctte, Indiana
(Pipronl)
6-~ethyl-2,J-quinoxalinedithiol cyclic-S,S-
dith iocarbona tc (axy th ioqu inox) (Quinomethionate)
aaychem corporation
Chcmagro Corporation, division
Kansas City, Missouri
(llorestan')
4-(~ethylsulfonyl)-2,6-dinitrQ-N,N-dipropylaniline
(Nitralin)
Shell Chemical Company
Agricultural Division
Denver, Colorado
(Planavinl)
4-(Methylthio)-J,S-xylyl ~ethylcarbamate
Bayche~ Corporation
Chemaqro corporation, division
Kansas City, Missouri
Methyl trithion (See: a,a-Dimethyl-S-chlorophenyl
thiomethyl phosphorodithioate)
Metron [See: O,O-Dimethyl.O-[p-nitrophenyl]
phosphorothioate)
~~v~nphos (See: a,a-Dimethyl a-(2-carbomethoxy-1-
methylvinyl] phosphate)
Milbam (Se~: Dimethyl1ithiocarbamic acid, zinc
salt under aubber processi~g Chemicals)
~ilo'1ardft (See:
s-t ridzin.:!)
2-Chloro-U,6-bis [fsopropylamino]-
Mit:t.?x (~\C~:
'Dodecdchloro-oc~abyd~o-1.J,4-~etheno-
-191
-------
2H-cyclobuta (cd] pentalp.ne)
~;ocap' (See:
dithioate)
a-Ethyl S,S-dipropyl pho~paoro-
t10linate (See:
carbothioate)
S-Ethyl hexahydro-1H-azepine-1-
~onosoJium methyl arsonate (See:
acid. monosodium salt)
l1ethanearsonic
tlonuron (See:
3-[p-Chlorophenyl]-1,1-dimethylurea)
~orestant (See: 6-~ethyl-2.3-qu~noxalinedithiol
cyclic-s,S-dithiocurbonate)
l1orocide. (See: 2-sec-Butyl-4,6-dinitrophenyl-3,3-
dimethylacrylate)
MIA 10637 (Set!:
Ethyl hydrogen 1-propyl phosphonate)
NPA (See:
N-1-Naphthylphthalamic acid)
Nabam (See: Ithylene bis (dithiocarbamic acid],
disodium salt)
Naled (See: O,O~Dimethyl 0-[ 1.2-dibromo-2,2-
dichloroethyl] phosphate)
Mapbthalene
1~Naphthalene acetamide ('-Naphthylacetamide)
nillmaster Onyx corporation
l1illmaster Cht!mical Company. division
Berkeley Chemical Department
aerkeley Heights, New Jersey
Rorer-Arrcham
Arr~hem Products, Inc., division
. Ambler, Pennsylvania
1-Naphthaleneucetic acid (1-Naphthylacetic
(NAA)
l1illmaster Onyx corporation
'l1illmaster Chemical Company, division
Berkeley Chemical Department
Derkeley Heights, New Jersey
Rorer-Amch~m .
Amchem Products. Inc.. division
Ambll:!r, Pennsylvania
acid)
1-~;d[>lat h,"\l"'ne~ctc!tic aci<1, ethyL
L~O!" c r- A;oc:. ~in
ester
192
-------
Amchem ProJucts, Inc., division
Ambler, P~nnsylv~nia
1-Naphthalen~acetic acid, sodium salt
~illma5ter Onyx Corporation
Millmaster Chemical Company, division
eerkeley Chemical tepartm~nt
Berkeley Heights, Nuw Jersey
Rorar-Amchem
Amchem Products, Inc., division
'mbler, Pennsylvania
Naphthenic acid, copper salt (See:
naphtbenate)
1-Naphtbyl N-methylcarbamate (Carbaryl)
Union Carbide Corporation
Chemicals and Plastics Division
Institute and South CharIest (Sevin.)
Copper
(2-Naphthyloxy) acetic acid
(j-Naphthoxyacetic acid) (0-( 2-!laphthyl]
glycolic acid)
~illmaster Onyx Corporation .
~illmaster ~hemical Company, division
.Oerkeley Chemical tepartment
Derk~ley Heights, New Jersey
(2-Naphtbyloxy) acetic acid, sodium salt
IHllmaster Onyx corporation
~illmaster ~hemical co~pany, division
Berkeley Chemical Dep~rtm~nt
Berkeley Heights, New Jersey
2-('-Naphthoxy)-N,N-di~thyl propionamide
Stauffer Chamica~ Company
Agricultural Ch~mical Division
.' Richmond, California
N-1-Naphthyll1hthalamic acid (NPA)
The Ansul Company
Chelnical Division
~arinette, Wisconsin
(Nap.talam)
Naptalam (See:
N-1-Naphthylphthalamic acid)
Neguvont (S~e: O,O-Dimethyl 2,2,2-trichloro-1-
hydroxyethyl fhosphonatc).
~emacidc (See: Q-2,g-Dichlorophenyl-o,O-Jiethyl
phu:;ph0["()thiodtC)
193
-------
!lemagon' (Sce:
1,2-Dibromo-J-chloropropane)
Sodium bor
-------
phosphorothioate)
Ortho-xenol
(S~e:
o-Pheny1phcnol)
Ov~x (See:
sultonate)
p-Chlorophenyl-p-chlorobenzene-
Ovotran' (See:
sulfollat~)
p-Chloropbenyl-p-chlorobenzene-
7-0xabicyclo (2.2.1) heptane-2.3-dicarboxylic
disod i um sal t (Aqua thol) (Hydrot hal)
pennwalt corporation
Ch~mical Division
Wyandotte, ~ichigan
acid,
(EndothaH)
Oxirane
(See:
Ethylene oxide)
Oxybis (tributyltin)
(See:
Bis (tri-n-buty~tin] oxide)
Oxythioquinox (See: 6-~ethyl-2.3-quinoxaline-
dithiol cyclic-S.S-dithiocarbonate)
Parathion (See: o,o-Dimethyl 0-
[p-nitrophcllyl] phosphorothioate)
Para%ate (See:
:tine salt)
Ethylene bis [dithiocarbamic acid],
Paridol (See: O,O-Dimethyl O-(p-nitrophenyl)
phosphorothioate)
Paris Green (See:
Copper acetoarsenite)
PCNB ~See:
PCP (See:
Pentachloronitrobenzene)
2,3,ij,5.6-Pentachlorophenol)
PZ:BC (See:
n-propylethyl-n-butylthiolcarbamate)
pebulate (See:
n-propyl ethyl-n-butylthiolcarbamate)
Pentac (S(!e:
Decachlorobis (2,4-cyclopentadien-1-yl])
Pentachloronitrobenzene (PCNB)
Olin Corporation
D~5igned products Division
Rochestpr, N~w Yotk
1!1du:o>trial Prr)d;jc~:> awl S(~r....ices Division
~clntosh, Alabama
(Terraclort)
125
-------
2,3,1.I,5,6-Pentachlorophcnol (PCP)
Annual Capacity
jAill!2~~~I-~~~~
Dover Chemical corporation
Dover, Ohio
Dow Ch~~ical U.S.A.
~iuland, ~ichigan
~onsanto Company
~onsanto Industrial Chemicals
Sauget, Illinois
Red Devil Paint Co.
Tacoma, .ashington
Sonford Ch~~ical Company
Ilou;:;ton, Texas
n.a.
(Dovicidet7)
15
company
. 26
(Chlorophen')
12
.n.a.
TOTAL
60
.~a1 not be operating.
Sources: Compiled in association vith the Chemical Economics Handbook,
and correspondence.
Pentachlorophenol, sodium salt (Sodium
pentdchlorophenate)
Dover Chemical corporation
Dover, Ohio
Dow Chemical U.S.A.
~idland, Michigan
:1on3anto Company
Monsanto Industrial Chemicals Company
Saugct, Illinois
3eu Devil Paint Co.
Tacoma, Washington
(Dovicide' G)
Pecchloromethyl :nercaptan (PMl\) (Perchloro-
methanot h iOl) (Trich lot"o~e thaneth io 1)
Stauffer ~hemical Compa~y
,Calhio chemicals, Inc., ~ubsidiary
Perry, Ohio
Perchloropentdcyclodecane (See: Dodecachloro-
octdhydro-l,3,I.I-metheno-2U-cyclobuta (cd]
pentalelle)
Perthi.ine;
ethan..)
(See:'
1,1-Dichloro-2,2-bis (p-~thylph~nyl]
196
-------
Pest~a$tcr' (See:
Bromornethane)
Ph
-------
Phenylmercury borate «(Dihydro;en borato]
phenylmercury)
C05dn Chemical corporation
Clifton, New Jersey
Royce Chemical Company
East Rutnerford, New J~rsey (Corubext)
Troy Chemical corporation
Newar~, New Jersey
Phenylmercury chloride (Chlorophenylmercury)
Phenylmercury dimethyldithiocarbamate (Phelam)
Phenylmercury 2-ethylhexanoate
Tenneco Inc.
Tenneco Chemicals, Inc.
Intermedi~tes Division
Elizabeth, New Jersey
Lon~ 8each, California
Phenylmercury hydroxide ([Hydroxymercuri]
(Phenylmercuric hydroxide)
~erck & Co., Inc.
Merck Chemical Division
Hawthorne, New Jersey
benzene)
Phenylmercury lactate ([Lactoyloxy] phen1l~ercury)
Phenylmercury naphthenate
nerck & Co., Inc.
nerck Chemical Division
Hawthorne, New Jersey
Tenneco Inc.
Ten.neco Chemicals, Inc.
Intermediates Division
Blizabeth, New Jersey
Pheny ~l!1ercur y nitrate.
Phenylmercury oleate ([Oleoyloxy]
w. A. Cleary Corporation
Nev Urunswick, New Jersey
Cosan Chemical corporation
. Clifton, New Jersey
nerck & Co., Inc.
aerck Chemical Division
Hawthorne, New Jersey'
Tenneco Inc.
Tenneco Chemicals, Inc.
Intermediates Division
Elizabeth, New Je=sey
LonlJ ucach, Cali[orllia
phenylmercury)
-------
Troy Chemical Corporation
Newark, New Jersey
Phenyl~~rcury propionate (Phenyl
mercur 1)
~c~ck & Co., Inc.
~erck Chemical Division
Hawthorne, New Jersey
(propionyloxy)
(l1etasoH 57)
Ph~nylmcrcury salicylate (Phenyl r~alicyloyloxy)
/r.ercury) ,
2-Phenylphenol (See:
o-Phenylpbenol)
Phordte (See: O,O-Diethyl S-(etbylthio] methyl
Fhosphorodithioate)
Phosdrinl (See: O,O-Dimetbyl O-(2-carbometboxy-
1-methylvinyl] phosphate)
Phosion. (See: Tributyl (2,4-dichlorobenzyl]
Fhosphonium chloride)
Phosphamidon (o-(2-Chloro-2- (diethylcarbamoyl)-1-
methylvinyl] O,a-dimethyl phosphate) (Oimecron)
Standard Oil Company of California
Chevron Chemical Company, subsidiary
Ortho Division
~4ryland Hciyhts. Missouri
Orlando, Florida
Richmond, California
South Pl~infield, New Jersey
Phosphorothioic acid, O-(2-chloro-1-(2,S-dicbloro-
phenyl] vinyl) o,a-diethyl ester (See: O,O-Ciethyl-O-
(2-cbloro-1- (2,S-dichlorophenyl) vinyl] phosphoro-
thioate)
Phthalimidomethyl-a,O-dimethyl phosphoroditbioate
(See: O,O-Dimethyl S-phthali~idomethyl phosphoro-
dithioate)
phytar. 560 (See:
cacodyli~ acid)
Picloram (See:
acid)
4-Amino-3.5,6-trichloropicolinic
Pin,tone (See:
2-pivaloyl-1.3-indandione)
Pip,~r(lli!l (Sec: 3-( 2-:1f!thylpipeddino) propyl-3,4-
d ic.:h 1 ora b.~l\z a a t e)
199
-------
Pip~razine (Diethylenedia~ine) (Hexahydro-1,4-diazine)
(li~xahydroPYl"azine) (Lumbrical) (Piperazidine) (pyrazine
bexahydr ide)
Pleming Laboratories, Inc.
Charlotte, North Carolina
Jefferson Che~ical Company, Inc.
Conroe, Texas
Rhodia Inc.
Np.v Drunsvick, Nev Jersey
Union Carbide Corporation
Chemicals and Plastics Division
Taft, Louisiana
Texa~ City, Texas
Piperazine dihydrochloride
Fleming Laboratories, Inc.
Charlott~, North Carolina
Jefferson Chemical Company, Inc.
Con roe, Texas
Polychemical Laboratories, Incorporated
Bronx, Nev York
Rohm and Haas Company
ihitmoy~r Laboratories, Inc., subsidiary
~yerstovn, Pennsylvania
Piperonal bis (2-(2'-n-butoxyethoxy) ethyl] acetal
McLaughlin Gormley King Company
ftinneapolis, Minnesota
(TropitaU)
Piperonyl butoxide ('-[2-(2-Butoxyethoxy) ethoxy]-
4. 5-metb y lened ioxy- 2- propy 1 toluene) (Bu tylcarbi tyl
(6-propylpiperonyl) ether) ([J,4-Methylenedioxy-6-
propylbenzyl) (butyl)-dietbylene glycol ether)
(6-Propylpiperonyl butyl diethylene glycol ether)
Alpha Laboratories Inc.
Denver. Colorado
P'I'IC corpocat.ion
Chemical Group
'Industrial Chemical Division
Baltimore, Maryland
/!cLauyhlin Gormley King Company
Minneapolis, Minnesota
/!~llmaster Onyx corporation
/!illmdster Chemical Company, division
Berkeley Chemical Department
Derkeley Heights, New Jersey
(Butoxidel)
Pipcon' (See: 3-( 2-l1ethylpiperidino] propyl-3,4-
dichlo~obcnzoate)
PiV.1H (SeE:':
2-pivaloyl-1,J-indandione)
200
-------
2-~iYaloyl-1,3-indan~ione (?indone)
indandione)
'acKcnzie Chemical Works, Inc.
Central Islip, New York
IIO'l'O~CO, Inc.
Clark, New Jersey
(2-Pivalyl-1-J-
(Piva1t )
2-Pivaloyl-1,3-indandione,
(2-Pivalyl-l,3-indandione.
I'IOTOI'ICO, Inc.
Clark, New Jersey
sodium salt
sodium salt)
(Pivalyn')
Pivalyn' (See: 2-Pivaloyl-1,3-
indandione, sodium salt)
Planavin' (See: 4-(McthylsulfonylJ-2,6-dinitro-
N,S-dipropylanitine)
PI'IA (See:
Phenylmercury acetate)
Polyacrylonitrile, hydrolyzed, sodium
American Cyanamid Company
Industrial Chemicals and Plastics
Linden, New Jersey
Organic Chemicals Division
Wopdbrid~e, New Jersey
salt
Division
Polychlorodicyclopentadiene isomers
(Polychloro-tetrahydro-methanoindene isomers)
Northvest Industries, Inc.
Velsicol Chemical corporation, subsidiary
Memphis, Tennessee (Bandanet)
Polyram (See: Dithiobisthiocarbonyliminoethylene
bis dithiocarbam1c acid, zinc salt)
pomarsol Z (See:
zinc ~4lt)
Potassium cyanate (KOCN)
American cyanamid Company
Lederle Division
Fine Chemicals Department
Linden, ~ew Jersey
Diamond Shamrock corporation
Diamond Shamrock Chemical Company
Chemetals Division .
Curtis Day, Maryland
Dimethyldithiocarbamic acid~
(cyanogumt 44)
prami tol ~ (Sp.e:
1,3,5-triazinc)
2-Methoxy-4,6-bis [isopropylamino]-
201
-------
Prefar' (See: 1/-( '-O,O-Diisopropyldithiophosphoryl-
ethyl) benzene sulfona~ide)
PreCoran' (Sec:
diphenyl ether)
2,4'-Dinitro-4-trifluoromethyl-
PrincepJ (See:
Simazine)
Primaze (See: 2,4-Uis (isopropylamino]-6-
~ethylthio-s-triazine)
Prolate (See: O,O-Dimethyl S-phthali~idomethyl
phosphorodithioate)
Prometone (See:
1,J,5-tria.zine)
2-~ethoxy-4,6-bis [isopropylamino)-
prometryne (See: . 2,4-Bis [isopropylamino)-6-
methylthio-s-triazine)
Propachlor (See:
2-Chloro-K-isopropylacetanilide)
Propanil (See:
J,4-Dichloropropionanilide)
Propazine (See:
s-triazine)
2-Chloro-4,6-bis [isopropylamino)
2-Propenal (See:
Acrolein)
2-Propen-1-ol (See:
Allyl alcohol)
Propham (See:
Isopropyl N-phenylcarbamate)
a-Ethyl S,S-dipropyl phosphoro-
Prophos (See:
dithioate)
Propoxur (See:
o-Isopropoxyphenyl methylcarbamate)
n-Propyl-di-n-propylthiolcarbamate
(S-Propyl dipt"opyltlliocarbamate) (Verno late)
Stautfer Chemical Company
. Agricultural Chemical Division
Cold Creek, Alabama
(Vernam')
n-Propyl ethyl-n-butylthiolcarbamale (PEBC)
(Pebulate) (S-Propyl n-butyl €thylthiocarbamate)
Stauffct" Chemical Company
A~t"icultut"al Ch3mical Division
Col(1 Cre,;>k, Alah..l1!\a
(Tilla:n#)
202
-------
n-Propyl isome (S~e: Di-n-propyl 6,7-methylene-
dioxy-j-mcthyl-1,2,3,4-tetrahydronaphtbalene-
1,2-dicarbox/late)
b-P~o~ylpiperonyl butyl diethylene glycol
ether (See: Piperonyl butoxide)
Prot~x (See:
Rotenone)
Pru!;;sic acid
(See:
Hvdroaen cyanide)
Pyrolmin' (See:
pyridazinone)
5-Amino-4-chloro-2-phenyl-3 (2HJ-
Pyrazon (See:
pyridazinone)
S-Amino-4-chloro-2-phenyl-3 (28J-
Pyr~thrins (Pyrethrum)
CPC International, Inc.
S. B. Penick & Company, division
Montville, New Jersey
FMC Corporation
Chemical Group
Industrial chemical Division
Baltimore, ~aryland
McLaughlin Gormley King Company
~inne~~olis, ~innesota
Prentiss Drug & Chemical Co., Inc.
New4rk, New Jersey
(Pyrocidet)
a-Quinolinol, copper salt (a-Hydroxyquinoline.
copper salt) (Copper a-quinolinolate) (Copper
oxinate) (copper oxyguinolate)
Ashland oil, Inc.
Ashland Chemical Company, division
.Chemical Products Division
. Gre4t ~eadows, New Jersey
Fer~o corporation
Ferro Chemical Division
Bedford, Ohio
Merck & Co., Inc.
Merck chemical Division
. Hawthorn~, New Jersey
Tenneco Inc.
Tenneco chemicals, Inc.
Intermediates Division
Elizabeth, ~ev Jersey
Long Beach, California
T~oy Ch~micdl Corpor~tion
Newolrk, New Jersey
(/1 illller' 1)
203
-------
Quinometbionatc (See: 6-Methyl-2.3-
quinoxalinedithiol cyclic S,S-dithiocarbamate)
Ramrod; (See:
2-Chloro-N-isopropylacetanilide)
2-Chloro-N,N-diallylacetamide)
Randox f (See:
Rhothane' (See:
DDD)
Roque' (See:
3',4'~Dichloropropionanilide)
Ro-neet' (See:
c.lrbamate)
S-Ethyl N-ethyl-N-cIclohexylthio-
Ronnel (See: O,O-Dimethyl 0-[ 2, 4,S-trichlorophenyl]
phosphorothioate)
Rotenone (1,2,12,12a-Tetrahydro-2-isopropenyl-a,9-
dim~thoxy (1) benzopyrano (3,4-b) furo (2, 3-H ] ( 1)
benzopyrcin-6-( 6aH )-one) (Protex)
Dlue Spruce Company
ldison, New Jersey
Chemical Formulators, Inc.
Chcmical Division
Nitro, West Virginia
CPC .In te.rna tional, Inc.
S. B. Penick & Company, division
Lyndhurst, New Jersey
FI'IC corporation
Chemical Group
Agricultural Chemical Division
Middleport, New York
North American Philips corp.
PEP], Inc., subsidiary
Thompson-Hayward Chemical Company, subsidiary
Leffingwcll Chemical Company, subsidiary
Brea, California (Tox-R')
Pren~iss Druq & Chemical Co., Inc.
. Newark, New Jersey
Ruelenct (See: 0-(4-tert-Butyl-2-chloropuenyl]-
O-methyl methylphosphoramiuate)
Rya~ia
CPC International, Inc.
S. B. Penick & Company, division
Lyndhurst, New Jersey
(Ryanicidel)
(prolin ')
North ~merican Philips Corp.
PEPI, Inc., ",ubsiuidry
Th orr p~on- iidY lid rd C hem i cal Company, :;u bsid i3ry
Leftin~wellChc~ical Co~pany, sUbsidiary
204
-------
area, California
(Bynotox')
S9P-1J32 (See: (S-6enzyl-J-furyl] :r.ethyl-2,2-dimethyl-
3-r2-mcthylpropenyl] cyclopropdnecarboxylate)
SIIDC (See:
salt)
N-Methyldithiocarbamic acid, sodium
Santophen' No.1 (See:
o-Benzyl-p-chlorophenol)
Seedrin (See:
Aldrin)
Se~onc' (See: 2-(2,4-Dicblorophenoxy) etbanol
sulfate, sodium salt)
Sevin' (See:
1~Napbtbyl N-methylcarbamate)
Silica gel (See:
Silica)
Silvex (See:
acid)
2-(2,4,S-Tricblorophenoxy] propionic
Simazine (2,4-ais [ethylamino]-6-cbloro-s-triazine)
(2-ehloro-4,6-bis (ethylamino)-s-triazine)
elba-Geigy corporation
Agricultural Division
ftcIntosh, Alabama
(Princep')
Sinbar (See:
methyluracil)
3-tert-Butyl-S-chloro-6-
Sinoxl General (See:
ammonium sal t)
2-sec-autyl-4,6-dinitropbenol,
Sinox' PZ (See: 2-sec-Butyl-4,6-dinitrophenol,
triethanolamine salt)
Sirma ~e' (See:
Dichlorobenzyl methylcarbamate)
Sodam (See:
sa L t )
Dimethyldithiocarbamic acid, sodium
Sodium acid methyl arsonate (See:
aClrl, monosodium ~aLt)
Methanearsonic
Sodium arsenite (ArSenious acid, sodium salt)
Alco Standard Corporation
ailler Chemical and Fertilizer Corporation, subsidiary
ilanover, Pcnn:.;ylv.lnia
Blue Spruce COlnpany
~di50n, New Jersey
Cl1cmp.:lr l:he:nical Co., Inc.
205
-------
Portland, Orcqon
Filo Color anJChcmical Corporation
Ncw~r~, New J~rsey
Los Anyeles Chemical Company
South Gate, California
~allinckroJt Chemical Works
Indu$trial Chemicals Division
St. Louis, Missouri
Pcnnwalt corporation
Chemical Division
Tacom4, Washington
Somp.rset Tire Co.
Bound Srook, New Jersey
Standard Oil Company of California
Chevron Chemical Company, subsidiary
Ortho Division
Maryland Heights, Missouri
Richmond, California
Triangle Chemical Company
I!acon, Gaor:Jia
Sodium chlorate
Sodium fluor ide
Sodium
Filte
fluoroacetate
Chemicals, Inc.
Nitro, West Virginia
Chemical Company, Inc~
Oxford, a.labama
("1080" Rodenticide)
o-Phenylphenol)
Tull
Sodium o-phenylphenate (See:
Sodium tetraborate (See:
Sodium borates)
Stabi~~ne' (See:
Butoxy~olypropylene glycol) .
Stam' (See: )'.4'-Dichloropropionanilide)
Strobane~ (See:
Chlorinated mixed terpenes)
Succinic acid, 2,2-dimethylhyJrazide (See:
Di~ethylamino succinamic acid)
N-
Suc~er-Stuff# (See:
Maleic ~ydrazide)
Sulfoxid\.! (1,2-M\?thylencdioxy-4-[ 2- (octylsulfinyl)
~coryl-l1 benzene) (n-Octyl sultoxide of isosafrol~)
(1-~~thyl-2-(3,4-methylpnQdioxy?henyl) ethyl oetyl
:3ulf,L(l(J."?)
2Q.6 ,
-------
c~c Int~rnational, Inc.
S. B. Penick & Co~pdny, division
~ontville, New J~rsey
Sulfur
Sutdn'
(See:
S-Ethyl diisobutylthiocarba~ate)
Systox' (See: O,O-Diethyl 0 (and S ]-2-[ ethylthio]
ethyl phosphorothioates)
2,4,S-T' (See:
(2,4,S-Trichlorophenoxy] acetic acid)
2,3,6-TBA (See:
2,3,6-Trichlorobenzoic acid)
'IBTO (See:
Bis (tri-n-butyltin)oxide)
TCA (See.:
Trichloroacetic acid)
2,4,S-TCPPA (See:
propionic acid)
2-(2,4,S-Trichlorophenoxy]
TEPP (See:
Ethylpyrophosphate)
'UBA (See:
2,3,S-Triiodobenzoic acid)
2,4,S-TP (See:
propionic acid)
2-(2,4,5-Trichlorophenoxy)
Tabatrex' (See:
D i-n-b u tyl succinate)
Tedian' (See: 4-chlorophenyl-2,4,5-trichloro-
pheny 1 sulfone)
Telone (See: 1,3-Dichloropropene, 1,2-dichloro-
propane mixture)
TeIn,;. (See:
3-( p-Chlorophenyl]-1, 1-dimethylurea)
Temikl (See: 2-Methyl-2-[methylthio) propionaldehyde
O-[methylcarbamoyl] oxime) ~
Terpacil (See:
3-tert-Butyl-5-chloro-6-methyluracil)
Terpene polychlorinates (See:
terpenes) ~
Chlorinated mixed
Terpinyl thiocyanoacetate (See:
thiocy~nodcetate)
Isobornyl
Terrdclor ~ (Sc~:
Pentachloronitrobenzcne)
207
-------
Terrazole' (See: 5-Ethoxy-3-trichlorometbyl-
1,2,4-thiadiazole)
cis-~ ([ 1,1,2,2-'rett"achlot"oethyl J thio)-4-
cyclohcxene-1,2-dicat"boximide (N-Tett"achlot"o-
ethylthio-l,2,J,&-tutrahydrophthalimide)
St~ndard Oil Company of California
Chevron Ch~mical Company, subsidiary
Ortho Division
Richmond, California
(Difolatanl)
2,J,5,6-Tetrachloro-4-(methyl sulfonyl) pyridine
Dow Chemical U.S.A.
Pittsbucg, California
2,3,4,6-Tett"achlorophenol
Dow Chemical U.S.A.
Midland, Michigan
(Dovicide' 6)
Tetrachlocoquinone (See:
Cbloranil)
O,O,O',O'-Tetraethyl 5,S'-methylene bis-
phosphorodithioate (See: Ethion)
Tetraethylpyrophospbate (See:
Ethylpyrophosphate)
. .
Tetraethylthiuram disulfide (See:
carbamoyl] disulfide)
Bis fdiethylthio-
Tetrahydro-J,S-dimethyl-23,l,3,S-thiadiazine-2-
thione (See: J,5-Dimethyltetrahydro-2H,1,J,S-
thiadiazine-2-thione)
1,2,12,.12a-Tetrahydro-2-isopropenyl-8,9-di~ethoxy
[ 1] bcnzopyrano (J, 4-b) furo [2, 3-h J ( 1) benzopyran-
6-(6aH]-one (See: Rotenone)
C,O,O',O'-Tetramethyl O,O.-thiodi-p-phenyl~ne
phosphorodithioate '
American cyanamid Company
Agricultural Division
Linden, New Jet"sey
Tet~amcthylthiuram disulfide (See:
thiocacbamoyl) disulfide)
(Abate.)
Bis (dimethyl-
Tctrdmethylthiuram monosulfide (See:
(di~cthylthiocarbamoy1J sulciue)
Bis
Tptra-n-pro?yluithior:opyro;.>ho5!Jh
-------
Stauffer Chemical Company
Agricultural Chemical Division
~t. P1easunt, Tennesse~
(Aspon J)
T hall i urn s 111 fat f!
American Sm~lting and aefining Company
Denv~r, Colorado
Thani tel (See:
Isobornyl thiocyanoacetate)
ThirneU (See: O,O-Diethyl S-( ethyl thio] methyl
phosphorodithioate)
Tbiocyanic acid, 2-(2-butoxyetho%y) ethyl ester
(See: 2-( 2-l3utoxyethoxy) ethyl thiocyanate)
Tbiodemeton (Se~: O,O-Diethyl S-(2-(ethylthio)
ethyl) phosphorodithioate)
2-Thio-3,S-dimethyl-1,3,S-tetrahydrothiadiazine
(See: 3,S-Dimcthyltetrahydro-2H,1,3,S-thiadiazine-
2-thione) .
Thiodiphenylamine (See:
Pl1enothiaz in e)
Thionazin (See: O,O-DiethylO-(2-pyrazinyl]
phosphorothioate)
Thiophal (S~e:
N-(Trichloromethylthio) phthalimide)
Thiophanate
w. A. Cleary corporation
New Brunswick, New Jersey
~-
Thiram (See: Bis (dimethylthiocarbamoyl) disulfide
under Rubber Processing Chemicals)
Tiguvon' (See: O,o,-Dimethyl 0-[ 4- (methylthio) -m-
tolyl] phosphorothioate)
Tillam' (See:
n-Propyl ethyl-n-butylthiolcarbamate)
Tok~ (See:
2,4-Dichlorophenyl-4-nitrophenyl ether)
p-Tolyl diiodomethyl sulfone
Abbott Laboratories
Chemical Division
North Chica~o, Illinois
T01'i).f:~ #
(See:
n- Ph'~nyl phenol)
209
-------
Tordon' (See:
4-Amino-3,S,6-trichloropicolinic acid)
Toxaphene (Chlorinated camphene)
Hercules Incorporated
Synthetics Department
Brunswick, Georgia
Sonford Chumical Company
Houston, Texas
Tenneco Inc.
Tenneco Chemicals, Inc.
Intermediates Division
fords, New Jersey
(Toxaphene.)
(Strobane n)
Treflan' (See: I,I,"-Trifluoro-2,6-dinitro-II,N-
dipropyl-p-toluidine)
TriLutyl (2,4-dichlorobenzyl) phosphonium
(Phos fon I)
Mobil Oil Corporation
Mobil Chemical Company, division
Industrial Chemicals Division
Charleston, South Carolina
ch loride
S,S,S-Tributyl phosphorotrithioate
Baychem corporation
Chemay.ro corporation, division
K4nsas City, Missouri
(DEFt)
Tributyl phospnorotrithioite
(S,S,S-Tributyl trithiophosphite)
Mobil oil corporation
, Mobil Chemical Company, division
Industrial Chemicals Division
. Mt. Pleasant, Tennessee
S,S,S-Tributyl trithiophosphite (See:
phosphorotrithioite)
Trich1~rfon (Sec: O,O-Dimethyl 2,2,2-trichloro-1-
hydroxyethyl phosphonate)
Tributyl
Trichloroacetic acid (TCA)
Dow Chemical U.S.A.
. Midland, Michigan
Trichloroacetic acid, sodium salt
Dow Chemical U.S.A.
did land, ftichigan
2.3,6-Trichlorobenzoic acid (2,3,6-TBA)
!1orer-t.mchcm
Amc~em rloducts, Inc., division
210
-------
Ambler, Pennsylvania
Fremont, Californid
St. Josuph, ~issouri
Tenneco Inc.
Tenneco Chemicals, Inc.
Intermedi~tes Division
Fords, New Jersey
2,3,6-Trichlorobenzoic acid, lithium salt
Tenneco Inc.
Tenneco Chemicals, Inc.
Intermediates Division
Fords, New Jersey
2,J,6-Trichlorobenzoic acid, potassium salt
Tenneco Inc.
Tenneco Chemicals, Inc.
Intermediates Division
Fords, New Jersey
1,1,1-Trichloro-2,2-bis (p-chlorophenyl) ethane
(See: DDT)
1,1,1-Trichloro-2,2-bis (p-methoxyphenyl) ethane
(Methoxychlor) (DMDT) (Methoxy DOT) (2,2-8is (p-
methoxyphcnyl] 1,1,1-trichlorQ~thane)
The Ansul Company
Chemical Division
Marinettp., Wisconsin
Chemical Po~mulators, Inc.
Chemical Division
Nitro, West Virginia
E. I. du Pont de Nemours & Company, Inc.
Ind~strial Chemicals Department
Linden, New Jersey
Prentiss Drug & Chemical Co.~ Inc.
Newark, New Jersey
("Moxie")
(tlarlatel)
Trichloro ton (See: 0,0- Dimet byl 2,2, 2-tr ichloi:o-
1-hydroxyethyl phosphonate)
Trichloromethanethiol (See:
lT1er~aptan)
(N-Trichloromethylmercapto)-q-cyclohexene-
1,2-clicarboximide (See: Captan)
Perchloromethyl
N-(Trichloromethylthio)-4-cyclohexene-1,2-
dicarDoxi~ide (See: Captan)
!>- (Tr ichlorolnct.i1yl th io)
(1'hio~hdl)
pnthalimide (?olpet)
211
-------
Stanuard Oil Company of California
Ch~vron Chemical company, subsidiary
Ortho Divi~ion
Pp.rry, Ohio
Stduffer Chemical Conpany
Calhio Chemicals, Inc., subsidiary
Perry, Ohio
(Phal tan')
N-Trichloromethylthiotetrahydrophtbalimide (See:
Captan)
Trichloronitromethane (See:
Chloropicrin)
2,4,5-Trichlorophenol
Dow Chemical U.S.A.
Midland, ~ichigdn (Dowicide' 2)
North Eastern Pharmaceutical and Chemical Company, Incorporated
Stamford, Connecticut
Occident.al Pctroleum Corporation
Hooker Chemical Corporation, subsidiary
Electrochemical 4nd Specialties Divisi,ons
Niagara falls, New York
Transvaal, Inc.
Jacksonville, Arkansas
2,4,5-Trichloro~henol, ethanolamine
GAF Corporation
Chemical Division
Linden, New Jersey
sa1"t
2,4,5-Trichlorophenol, sodium salt
Dow, Chemical U.S.A.
Midland, Michigan
(Dowicidet B)
2,4,6-Trichlorophenol
Dow Chemical U.S.~.
Midland, ~ichigan
(2,4,S-Trichlorophenoxy) acetic
Dow Chemical U.S.A.
Midland, Michigan
Transvaal, Inc.
Jacksonville, Arkansas
acid (2.. 4, 5-T)
(2,4,S-Trichlorophenoxy)acetic'acid, butoxyethanol ester
Dow Chemical n.S.A.
Midland, Michigan
(2.4,5-Trichlorophenoxy) acetic acid, n-butoxyetbyl ester
ROL.~r-.~or.ci,cm
A~ch@m Products, Inc., divi~ion
Ambl~r, Pennsylv~nia
212
-------
F~cmont, California
St. Joseph, ~is~ouri
(2,~,5-Trichlorophcnoxy)acetic acid, butoxypolypropylcneglycol ester
Dow Ch~~icdl U.S.~.
~idland, ~ichigan
(2,4,5-Trichlorophenoxy) acetic
Chcmpar Chereicdl co., Inc.
Portland, Oregon
PUI-Go~don corporation
Kdnsas City, Kansas
Transvaal, Inc.
Jacksonville, Arkansas
acid, n-butyl ester
(2,4, 5-Tricblorophenoxy) acetic acid, sec-butyl ester
Dow Chemical U.S.A.
~idland, Michigan
(2,~,5-Trichlorophenoxy)acetic
linoleyl amine salt
Transvdal, Inc.
J4cksonville, Arkansas
acid, N,N-dimethyloleyll
(2,Q,S-Trichlorophenoxy)acetic acid, 2-ethylbexyl ester
(See: (2,~,5~TrichlorophenoxYJacetic acid, iso-octyl ester)
acid. iso-octyl ester)
(2,4.5-Trichlorophenoxy) acetic acid. iso-octyl ester
(l,4,5-T, 2-ethylhexyl ester)
Do~ chemical U.S.A.
Midland, Hicbigan
North American Philips corp.
PEPI, Inc., subsidiary
Tho~pson-~aywdrd Chemical Company, subsidiary
Kansas City, Kansas
PBI-Gordon corporation
Kansas City, Kansas
Riverdale Chemical Company
Chicago Heigbts, Illinois
Rorer-Amchem
Amchem products, Inc., division
Au-bler, Pennsylvania
Fremont, california
St. Joseph, Missouri
Transvaal, Inc.
Jacksonville, A~kansas
(2,4,5-TrichlorophenoxY)dcetic
(2,4,5-1 dmine)
Ch£!mpar Cheu,icaL Co., Inc.
Portland, Ore'jon
acid, triethylamine salt
213
-------
Dow Chemical U.S.A.
~idlanJ, ~ichigan
Transvaal, Inc.
Jacksonville, Arxansas
2-(2,4,5-Trichlorophenoxy) propionic acid
(2,!I,5-TCPPA) (2,4,5-T[') (Fenoprop) (Sil vex)
Dow Chemical U.S.A.
~idland, Michigan
Millmaster Onyx corporation
Killmaster Chemical Company, division
B~rkele1 Chemical Department
B~rkeluy Hei~hts. New Jersey
Transvaal, Inc.
Jacksonville, Arkansas
(2,4,5-Tricblorophenoxy) propionic acid, n-butoxyethyl ester
Riverdale Chemical Company
Chicago Heights, Illinois
(2,4,5-Triculorophenoxy) propionic acid,
2-ethylhexyl ~ster (See: (2,4,S-Trichlorophenoxy]
propionic acid, iso-octyl ester)
(2,4,S-Trichlorophenoxy) propionic acid, iso-octyl ester
([2,4,5-Trichlorophenoxy)propionic acid, 2-ethylhexyl ester)
North American Philips Corp.
PEPI, Inc., ~uh~idiary
Thompson-Hayward Chemical Company, subsidiary
Kansas City, Kansas
Riverdale Chemical Company
Chicago Heights, Illinois
(2,4,S-Trichlorophenoxy) propionic acid, sodium salt
Killmazter Onyx corporation
Millmaster Chemical Company, division
Derkeley Chemical Department
. Berkeley Heights, N~w Jersey
Riverdale Chemical Company
Chicago Heights, Illinois
(2,3, b-Trichloropbenyl) acetic acid,
Rprer-Amchcm
Amchem Products, Inc., division
Ambler, Pennsylvania
Fremont, California
St. Jose~h, Missouri
sodium salt
(Fenac')
Tridex (See:
Di~thyl dithicbis [thionoformate))
.,-,d-Trifluoro-2,6-dinitro-N,~-dipro?yl-p-
tolu i<1 in~~ (T [' i fl u [' <11 in)
214
-------
Eli Lilly and Company
Tippecanoe L~bocatories
Lafayette, Indiana
(Tref lanl)
3-(m-Trifluocomethylphenyl)-1,l-dimetbylurea
(See: 1, 1-Dilnethyl-3-[ I, I, '-trifluoro-;r,-
tolyl] urea)
2,3,5-Tciiodobenzoic acid (TIBA)
Mallinckrodt Chemical Works
Industcidl Chemicals Division
Ral~igh, North Carolina
Borer-i\mcnem
Amchem Pcoducts, Inc., division
Amblec, Pennsylvania
Tris (2-bydcoxyethyl) (phenylIr.ercuri) ammonium lactate
i. A. Cleary corporation
New Brunswick, lie'll Jersey
TrUhion' (See: O,O-Diethyl-( p-cblorophenyl.-
thiomethyl] phosphorodithiodte)
Trolene' (See: 0,0-DimethylO-[2,ij,5-trichloro-
phenyl] phosphorothioate)
Tropi tal' (See:
ethyl) acetal)
Piperonal bis (2-(2'-n-butoxyetboxy)
Ttlpersan' (See:
2-(2~Methylcyclobexy1J-]-pbenylurea)
Ucab' (See:
l,l-Dimetbyl-]-pbenylurea tricblocoacetate)
Urox' tSee: 3-(p-Chlocophenyl]-1,1-dimetbylurea
ttichloroacetate} .
V-lOt (See:
BiS-l,ij-bromoacetoxy-2-butene)
Y-C 13; (See: 0-2,ij-Dichlorophenyl 0,0-
diethyl phosphorothioate)
YP/I (See:
N-nethyldithiocarbamic acid, sodium salt)
Yancide# (See:
ferric salt)
Dimethyldithiocarbamic acid,
Vapan# (See:
N-/lethyldithiocacbamic acid, sodium salt)
Vapona3 (See:
2,2-Dichlorovinyl dimethyl phosphate)
Ve'J~d.:!x II (Sep.:
2-Chlocoallyl diethyldithio-carbamate)
215
-------
Yenzar' (See:
Lenacil)
Ver~igcn (Sec:
J-Arnino-2,S-dichlorobenzoic acid)
Vernal!1i (See:
n-Propyl-n-propylthiolcarb«~ate)
VcrnoL\te (See:
n-Propyl-di-n-propylthiolcarbamate)
Viddcn D (See: 1,3-Dichloropropene, 1,2-
dichloropropane mixture)
OI.Hbex' (See: O,O-Dimethyl O-p-[dimethylsulfalr.oyl]
phenyl phosphorothioate)
Warfarin (3-[I-Acetonylbenzyl]-4-hydroxycoumarin)
(3-'-Phenyl-'-acetylethyl-4-hydroxycoumarin)
(Coumafene)
Blue Spruce Company
Edison, New J~rsey
MOTOMCO, Inc.
Clark, New Jersey
Prentiss Drug & Chemical Co., Inc.
Newark, New Jersey
Weed Chek (See:. [2,4-Dichlorophenoxy] acetic acid,
lithium sa.lt)
Yomesan (See: 2',S-Dichloro-4'-nitrosalicylanilide,
2-aminoethanol salt)
Zinc dimethyldithiocarbamate-cyclohexylamine complex (20: mixture)
Nor-Am Agricultural Products, Inc.
Chicago, Illinois
Zinc phosphide
Occidental Petroleum corporation
Hooker Chemical Corporation, subsidiary
~lectrochemical and Specialties Divisions
. Niagara Falls, New York .
Zineb (See:
zinc salt)
Ethylene bis (dithiocarbamic acid],
.
Zinophos' (See: O,O-DiethylO-[2-pyrazinyl]
phosphorothioate)
Zirdm (5ea: Dimethyldithiocarbamic acid,
zinc s~lt under Rubber Processing Chemicals)
l:ok:,'ir J (St':e:
dmill<.! !;i! 1 t)
Polychlorobenzoic acid, dimethyl-
216
-------
APPENDIX D
MIDWEST RESEARCH INSTITUTE SUMMARY OF PESTICIDES NOT LISTED
BY THE U.S. TARIFF COMMISSION
217
-------
Table D-l.
PESTICIDES NOT LISTED IN "PESTICIDES AND RELATED
SECTION OF ~TIC OR~NIC CHEMICALS
UNITED STATES PRODUCTION AND SALES
(ANNUAL)
BY UNITED STATES TARIFF COMMISSION
PRODUCTS"
Organics
Inorganics
Fumigants
Heavy metals
Acrolein
Carbon disulfide
Carbon tetrachloride
Chloropicrin
Dichlorobenzene
Ethylene dibromide
Ethylene oxide
Formaldehyde
Naphalene
Fungicides
Copper sulfate
Calcium arsenate
Lead arsenate
Sodium arsenite
Acid copper chromate
Ammonical copper arsenite!1
Chromated copper arsenates~1
("CCA" salts)
Chromated zinc chlorid~1
Fluoro chrom arsenate phenol~1
Potassium hexafluoroarsenate!1
Dithane M-45ID and Manzate 20~1
Niacide@
Polyram@
Thiram
Ziram
Others
Othe rs
Aluminum phosphide
Ammonium sulfamate
Calcium cyanid~1
Cryolite~}
Phosphoric aci~1
Phosphoru~1
Sodium chlorate
Sodium chlorate-borate
Sulfur and lime sulfur
Biphenyl
Metadehyde
Orthophenyl phenol
Sodium fluoroacetate
Other disenfectants, bacterio-
state, germicides and water
purifiers
Fossil fuel derivatives
Coal tars~1
Creosot~1
Petroleum oil~1
!-I
Not included in the SRI list of pesticides.
218
-------
APPENDIX E
MIDWEST RESEARCH INSTITUTE ESTIMATED
PESTICIDE PRODUCTION IN 1972
219
-------
ESTIMATED PESTICIDE PRODUCTION IN 1972
PART A.
INSECTICIDES AND RELATED PRODUCTS
CYCLIC INSECTICIDES. NEMATOCIDES, .
RODENTICIDES, REPELLANTS, ATTRACTANTS,
SYNERGISTS AND ADJUVANTS
ORGANOPHOSPHORUS INSECTICIDES
Abate\8.>
Azinphosmethyl (Guthion@)
Carbophenothion
Chlopyrifos (Dursban@)
Ciodrin@
Coumaphos
Crufomate
Diazinon
Dioxathion
Dyfona te@
Fensulfothion
Fenthion
Leptophos
Methyl Parathion
Parathion
ProIa te (Imidan@)
Ronnel
Unassigned Production
Subtotal
ALDRIN-TOXAPHENE GROUP
Aldrin
Chlordane
Dieldrin
Endrin
*
Included in Unassigned Production.
220
Tariff
Commiss ion
Production
Data
51. 08
44.39
(95.46)
MRI
Es tima ted
Production
*
*
*
*
*
*
*
10
*
*
*
*
*
51. 08
13
*
*
21.38
(95.46)
14
20
*
*
-------
Heptachlor
Toxaphene
Unassigned
Subtotal
Production
CARBAMATE INSECTICIDES
£-sec-Butylphenyl-N-~ethylcarbamate
£-Chlorophenyl-N-methylcarbamate
Carbofuran (FuradanCB:»
Carbaryl (SevinCB:»
Formetanate
o-Isopropylphenyl-N-methylcarbamate
Metalkamate
m-Tolyl-N-methylcarbamate
Subtotal
CHLORO-ORGANIC INSECTICIDES
BHC and Lindane
Chlorobenz Ua te
Chloropropylate
DDD (TDE)
DDT
Dicofol (Kel thane<8> )
2,6-Dimethyl-3,S-dichloro-
4-pyridinol
Endosulfan
Kepone
Methoxychlor
Mirex
Perthane@
Tetradifon
Subtotal
* Included in Unassigned Production.
221
Tariff
Comission
Production
Data
141. 86
(141. 86)
MRI
Estimated
Production
7
95
5.86
(141.86)
*
*
6
53
*
*
8
*
(67.5)
*
*
*
*
40
*
*
*
*
*
*
*
*
(59.4)
-------
ALL OTHER CYCLIC INSECTICIDES, ETC.
INSECTICIDES, N.E.C.
Bacillus thuringiensis
Binapacryl
2-(p-tert-Butylphenoxy)cyclohexyl-
2-propynl sulfite
N-(Phenyl-2-nitropropyl)
piperidine
NEMATOCIDES
Dichlofenthion
Thionazin
RODENTICIDES
Diphacinone
Pindone
Warfarin
INSECT ATTRACTANTS AND REPELLANTS
Deet
2-(3,4-Dichlorophenyl)-2,2,4-
oxadiazoline-4-methyl-3,5-dione
MGK-326@
Trimedlure
SYNERGISTS AND ADJUVANTS
Heliotropin acetal
l,2-Methylenedioxy-4-
[2-(octylsulfinyl)propyl]benzene
MGK-264@
Piperonyl butoxide
* Included in Unassigned Production.
Tariff
Commission
Production
Data
222
MRI
Estimated
Production
*
*
*
*
*
*
*
*
*
*
*
*
*
*
*
*
*
-------
Tariff
Commission
Production
Data
MR.I
Estimated
Production
UNASSIGNED PRODUCTION
132,15
25,15
Subtotal, other cyclic insecticides
132.15
~OTAL, CYCLIC INSECTICIDES AND RELATED
PRODUCTS
369.47
369.47
ACYLIC INSECTICIDES, NEMATOCIDES,
FUMIGANTS AND SOIL CONDITIONERS
ORGANOPHOSPHORUS INSECTICIDES
Aspon@
Demeton 0
Dichlorvos (DDVP)
Dicrotophos
Dimethoate
Disulfoton
Ethion
Ma 1a thion
Mevinphos
Moni to:r
-------
Tariff
Commission
Production
Data
MR.!
Estima ted
Production
ACYLIC INSECTICIDES, NEMATOCIDES,
FUMIGANTS AND SOIL CONDITIONERS
NEMATOCIDES
Aldicarb
Prophos
*
*
SOIL FUMIGANTS
Chloropicrin
DBCP
Dichloropropene and mixtures with
rela ted products
Methyl bromide
Methyl isothiocyanate
(sales: 15.23)
5
15
24.63
20
24.63
*
SOIL CONDITIONERS
polyacrylonitrile, hydrolyzed,
sodium salt
15
UNASSIGNED PRODUCTION
Subtotal
104.3
128.93
49.3
128.93
TOTAL, ACYLIC INSECTICIDES AND RELATED
PRODUCTS
194 . 11
* Inc~uded in Unassigned Production.
224
-------
PART B.
HERBICIDES AND RELATED PRODUCTS
CYCLIC HERBICIDES AND PLANT HORMONES
TRIAZINES
Ametryne
Atrazine
Prometryne
Propazine
Simizine
Subtotal
PHENOXIES
Bromoxynil
4-CPA
2,4-D, dimethylamine salt
2,4-D, acid, esters and other salts
2,4-DB
MCPA
Silvex
2,4,5-T and derivatives
4-Chloro-2-methylphenoxy
butyric acid
Subtotal
ANILIDES
Alachlor
Butachlor
Propachlor
propimil
Subtotal
* Included in Unassigned Production.
225
Tariff
Commission
Production
Data
22.67
MR.I
Estima ted
Production
*
95
*
*
8
(110.0)
*
*
22.67
30
*
*
*
7
*
*
(67.67)
24
5
35
7
( 71.,0 )
-------
DINITRO PHENOLS AND ANILINES
Benefin
Dinoseb
DNOC
Nitralin
Tri£1uralin
Subtotal
AMIDES, IMIDES AND HYDRAZIDES
Diphenamid
Maleic Hydrazide
UREAS
Chloroxuron
Diuron
Fluometuron
Linuron
Monuron
Monuron-TCA
Siduron
Subtotal
URACILS
Broma c il
Terbacil
BENZOICS AND RELATED COMPOUNDS
Chloramben and derivatives
DCPA
Dicamba
2,S-Dichloro-6-nitro-
benzoic acid, Na salt
Endothall
Picloram
Subtotal
* Included in Unassigned Production.
226
Tariff
Commission
Production
Data
4.47
MR.I
Estimated
Production
*
*
*
*
21
(30.0)
*
4.47
*
8
*
*
*
*
*
(18.0)
8
*
20
*
*
*
*
*
(29.5)
-------
Ta riff MRI
Commission Estimated
Production Production
CARBA}~TES AND THIOCARBAMATES
Chloropropham (CIPC) *
Cycloate *
Propham (IPC) *
OTHER CYCLIC HERBICIDES
Bandane(8J *
Barban *
Bensulide *
Gibberell ic acid *
3~Indolebutyric acid *
Molinate *
I-Naphthaleneacetic *
acid and derivatives *
Naptalam *
Nitrofen *
Phosphon *
UNASSIGNED PRODUCTION 344.79 77 .09
TOTAL, CYCLIC HERBICIDES
371.73
371.73
ACYCLIC HERBICIDES AND PLANT HORMONES
AMIDES
CDAA CRandox'.!:V)
6
THIOCARBA}~TES AND RELATED COMPOUNDS
Butylate
CDEC
Diallate
EPI'C
Pebulate
Triallate
Vernolate
6
*
*
5
*
*
*
* Included in Unassigned Production.
227
-------
Tariff MR.I
Commission Estimated
Production Production
CHLOROALKYLACIDS
*
Dalapon D.3
TCA
PHOSPHORUS COMPOUNDS
Ethephon *
DEPQ:!) 5
Merphos *
ORGANO ARSENICALS
Cacodylic Acid and Salts *
Methane Arsonic Acid Salts, Total 30.70
DSVU\ 6
MSMA 24
Alkylammonium Salts *
OTHER ACYCLIC HERBICIDES
DMSA *
EXD *
UNASSIGNED PRODUCTION 48.88 16.28
TOTAL, ACYCLIC HERBICIDES
79.58
79.58
* Included in Unassigned Production.
228
-------
PART C.
CYCLIC FUNGICIDES
MERCURY FUNGICIDES
PMA
Phenyl mercuric oleate
Other mercury compounds
COPPER FUNGICIDES
Copper 8-Quino1inate
Copper Naphthenate
POLYCHLORO AROMATICS
Chloroneb
Chlorotha1oni1 (Daconi1~)
PCNB
Pentachlorophenol and salts
2,3,4,6-Tetrachloropheno1
2,4,S-Trichloropheno1 and salts
2,4,6-Trichloropheno1
Subtotal
CHLOROALKYL IMIDES
Captan
Captafo1
Folpet
OTHER CYCLIC FUNGICIDES
Benomyl
Benzylbromoacetate
2,6-Bis(dimethylaminomethyl)-
cyclohexanone
* Included in Unassigned Production.
229
FUNGICIDES
Tariff
Commis s ion
Production
Data
.31
.28
.27
.04
2.21
49.70
MRI
Estimated
Production
.31
.28
.27
.04
2.21
*
*
*
49.70
*
18
*
(70.35)
:p
*
*
*
*
*
-------
OTHER CYCLIC FUNGICIDES (Concluded)
2'-Bromo-4'-hydroxyacetophenone
5-Chloro-2-benzothiazolethiol,
laurylpyridinium salt
Cyanomethylthiobenzothiazole
Dinocap
Diphenylammonium propionate
DMTT
'Dyrene\tV
Ethoxyquin
Hexahydro-I,3,5-triethyl-s-triazine
Hexahydro-1,3,5-tris(2-hydroxy-
ethyl)-s-triazine
2-Mercaptobenzothiazole, salt
Piperalin
Terrazo1e(!3)
UNASSIGNED PRODUCTION
Tariff
Commission
Production
Data
45.36
MRI
Estimated
Production
*
*
*
*
*
*
*
*
*
*
*
*
*
22.35
98.16
TOTAL, CYCLIC FUNGICIDES
98.16
ACYCLT0 FUNGICIDES
DITHIOCARBAMIC ACID DERIVATIVES
Dimethyldithiocarbamic acid, K salt
Dimethyldithiocarbamic acid, Mn salt
Ethylene bis(dithiocarbamic acid),
diammonium salt
Ferbarn
Maneb
Nabam
Metham (SMDC)
Zineb
Unassigned Production
* Included in Unassigned Production.
230
40.44
*
*
*
*
15
*
5
8
12.44
-------
Tariff
Commission MR.I
Production Estimated
Data Production
OTHER ACYCLIC FUNGICIDES
Bis-l,4-bromoacetoxy-2-butene *
N,N-Bis(phosphonomethyl)glycine *
Cadmium succinate *
Chloromethoxypropy1mercuric acetate *
Copper tallate *
Dimethylthiocarbony1disu1fide *
Disodium cyanodithioimidocarbamate *
Dodine *
2-Hydroxypropy1methanethio1
sulfonate *
Korax *
PETD *
Unassigned production 4.21 4.21
TOTAL, ACYCLIC FUNGICIDES
44.65
44.65
* Included in Unassigned Production.
231
-------
~
TECHNICAL REPORT DA TA
(Please read Im;Lr.Jcciolls 011 rhe rere!'!e before completing)
1. REPORT NO. 12. 3. RECIPIENT'S ACCESSIOI'+NO.
EPA-600/2-77 -023h
4. TITLE AND SU8TITLE 5. REPORT DATe:
Industrial Process Profiles for Environmental Use: January 1977
Chapter 8. Pesticides Industry 6. PERFORMING ORGANIZATION COOE
7. AUTHOR(S) 8. PERFORMING ORGANIZATION REPORT NO.
Terry B. Pars ons, Editor
9. PERFORMING OROANIZAT10N NAME AND ADDRESS 10. PROGRAM ELEMe:NT NO.
Radian Corporation JAB015: ROAP 2IAFH-025
P.O. Box 9948 11. CONTRACT/GRANT NO.
Austin, Texas 78766 68-02 -1319, Task 34
12. SPONSORING AGe:NCY NAME AND ADDRESS 13. TYPE OF jf.PORT 70 PERIOD COVERED
EPA~ Office of Research and Development Initial; 8 75-11 76
Industrial EnlTironmental Research' Laboratory 14. SPONSORING AGENCY COOE
Research Triangle Park, NC 27 711 EPA-ORD
15. SUPP1_EMENTARY NOTES Chapter author is F. 1. Honea (Midwest Research Institute). Pro-
ject officer 1. A. Yifcoat is no longer with EPA: contact G. Tucker (IERL-RTP) '
Mail DrOD 63. 919 549-8411 Ext 2745
16. ABSTRACT The catalog was developed to aid in defining the environmental impacts of
U.S. industrial activity. Entries for each industry are in consistent format and form
separate chapters of the catalog. The pesticides industry produces organic chemicals
used: to control agricultural pests, to disinfect and condition soil, and as plant hor-
mones. The inorganic chemicals, petroleum products, and creosote used as pesti-
cides are specifically excluded from this chapter. The industry is discussed in 12
segments: simple and aromatic chlorinated hydrocarbons; diene-based; organophos -
phates; carbamates and thiocarbamates; triazines; anilides; ureas and uracils; nitra-
ted hydrocarbons; other nitrogenous; organoal~senicals and organometallics; micro-
bial or natural derivatives; and others. Thirteen chemical trees, 17 process flow
sheets, and 37 process descriptions characterize the industry. For each process
des cription, available data is presented on input materials, operating parameters '
utility requirements, and waste streams. Related information, provided as appen-
dices, includes company, product, and raw material data.
17. KEY WORDS AND DOCUMENT ANALYSIS
a. D ESCR I PTO RS b.IDENTIFIERS/OPEN ENDED TERMS C. COSA TI Field/Group
Pollution Plant Hormones Process Assessment 13B 06A, 06C
Industrial Processes Environmental Impact l3H
Chemical Engineering 07A
Pes tic ides 06F
Organic Chemistry 07C
Soil Chemistry 02A
18. OISTRISUTION STAT:;'V1ENT 19. SECURITY CLASS (Tilis Repcrr) i 21. '''~40; PAGES !
Unclass Hied
Unlimited 20. SECURITY CLASS (Tilis pagel 22. PRICE
Unclassified
EPA rorm 2220.1 (9-73)
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