WATER POLLUTION CONTROL RESEARCH SERIES
16020 EWC 04/71
         Catalog of Pesticide
             NMR Spectra
ENVIRONMENTAL PROTECTION AGENCY • RESEARCH AND MONITORING

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        WATER POLLUTION CONTROL RESEARCH SERIES
The Water Pollution Control Research Series describes
the results and progress in the control and abatement
of pollution in our Nation's waters.  They provide a
central source of information on the research, develop-
ment, and demonstration activities in the Environmental
Protection Agency, through inhouse research and grants
and contracts with Federal, State, and local agencies,
research institutions, and industrial organizations,

Inquiries pertaining to Water Pollution Control Research
Reports should be directed to the Head, Project Reports
System, Office of Research and Monitoring, Environmental
Protection Agency, Room 801, Washington, D.C. 20242.

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                       CATALOG OF PESTICIDE

                           NMR SPECTRA
                                   by
                 Enviroiiiiiental Protection Agency
                   Southeast Water Laboratory
                     Athens, Georgia  30601
                       Project  #16020  EWC
                            April 1971
For sale by the Superintendent of Documents, U.S. Government Printing Office, Washington, D.C. 20402 - Price $1.50

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                         EPA Review Notice

This report has been reviewed by the Water Quality Office,
EPA, and approved for publication.  Approval does not signify
that the contents necessarily reflect the views and policies
of the Environmental Protection Agency, nor does mention of
trade names or commercial products constitute endorsement or
recommendation for use.

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                             ABSTRACT
This catalog contains the 100-MHz NMR spectra of 114 organo-
phosphorus, DDT, and carbamate pesticides and a brief discussion
of their most important features.  Chemical shifts and coupling
constants are shown on each spectrum.
                                 111

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                        CONTENTS
Section
Page
   I  Introduction                                     1
  II  Experimental                                     3
 III  Discussion
      A.  The Organophosphorus Pesticides              5
      B.  DDT and Related Compounds                   61
      C.  The Carbamate Pesticides                    93
  IV  Index to Spectra                               137
   V  Acknowledgments                                149
  VI  References                                     151
 VII  List of Publications Resulting from this Work  153
VIII  Appendix:  Chemical Names and Sources of the
      Pesticides                                     155

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                             SECTION I

                            INTRODUCTION

Pesticides  are inportant sources of water contamination.  Individual
pesticides  or their degradation products must often be identified if
the water quality is to be protected and improved.  Nuclear magnetic
resonance (NMR) spectroscopy provides unique structural information (1)
that cannot be obtained from infrared spectroscopy, mass spectrometry,
and gas chromatography (the primary instrumental methods currently used
to identify water contaminants).

Interpretation of NMR spectra is enhanced when spectra of known similar
compounds are available for comparison.  Since few pesticides have been
included in NMR spectral catalogs, we recorded and interpreted spectra
of three important classes of pesticides and some of their degradation
products.  Spectral interpretations were discussed in previous publica-
tions (2-5), but only a few spectra were included.

This catalog contains spectra of 114 compounds arranged according to
molecular structures:
     1.  Organophosphorus pesticides
         a.   Phosphomethoxy [(CH30)2-P]
         b.   Phosphoethoxy [(C2H50)2-P]
         c.   Miscellaneous
     2.  DDT and related compounds — pesticides and several known or
         proposed metabolites with the substitute diphenyl
         methane skeleton.
     3.  Carbamate pesticides.

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Chemical names and sources of the compounds are listed in the Appendix
in the order they appear in this publication.  Section IV is an
alphabetical index of the common names and trade names of all compounds
in this catalog.

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                            SECTION II

                           EXPERIMENTAL
The  100-MHz spectra were recorded with a Varian HA-100 NMR spectrometer
equipped with a variable-temperature probe and a homonuclear spin
decoupler.  Solutions  (300 mg/mlj were prepared in deuterochloroform,
except when other solvents or less concentrated solutions had to be used,
or when changing solvent or concentration produced a desirable chemical
shift.  Each spectrum shows chemical shifts (T values with reference to
the  internal standard, tetramethylsilane).  Sweep widths of 1000 Hz or
500 Hz were used, but portions of some spectra were expanded for more
detailed analysis.  In some cases homonuclear spin decoupling, inte-
gration, protonation with trifluoroacetic acid, D20 exchange, temperature,
solvent and concentration variations,  and supplemental 60-Miz spectra
were needed for spectral interpretation.

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                            SECTION III

                            DISCUSSION
THE ORGANOPHOSPHORUS PESTICIDES
Signal splittings due to coupling of phosphorus with hydrogen complicate
these spectra.  Coupling constants, inversely proportional to the P-H
distance, vary from 0.5 to 18 Hz.  The aromatic proton signals of ronnel,
dicapthon, Ruelene, Zytron, methyl parathion, ethyl parathion and
paraoxon, have a small splitting due to P-H coupling through four and/or
five bonds.  The phosphoethoxy methyl signals (T 8.59-8.67, J = 0.5-1.2 Hz)
also show P-H coupling through four bonds.

Each spectrum of the phosphomethoxy compounds exhibits a doublet
(J = 11-16 Hz, T 6.1-6.3) due to the CH,0-P protons coupled through oxygen
to phosphorus.  In malathion, malaoxon, Dibrom, and Neguvon, each doublet
exhibits a smaller splitting (<2Hz).  Two methoxyl groups are attached
to the phosphorus atom and an asymmetric carbon atom is present; therefore,
this splitting is actually a chemical shift difference due to a small
magnetic non-equivalence of the methoxyl groups.  Similarly, methylene
groups of several phosphoethoxy compounds (Thimet, Di-Syston, Trithion
and ethion) produce 16, rather than the expected eight, peaks.  Each non-
equivalent methylene group is coupled with methyl protons to produce a
quartet that is further split by phosphorus.  The signals of the phospho-
ethoxy methylene protons appear at T5.65-5.91 with P-H coupling of 8-10 Hz.

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                                                                                                0.5(P-H)
                                                                                                7 (H-H)
                                                                                               10 (P-H)
                                                                                       10

-------
                                                                                  A-46
01
en
        CH3CH2CH2O    OCH2CH2CH3
                                                                                                   a


                                                                                                   b
9.03


8.27



5.88
 7

ftS(P-H)

 7 (H-H)
                                                                                            10

-------
                                                                                      A-47
    Falon*
  750
  T
tn
                              tb)
                                 III
(b)
                                                      (bl   (b)
                                                     a   5.4-6.7


                                                     b   Z6-?.4
                                                                                                 10

-------
                                                                                   A-48
     Merphos
Jo

T
T    H  (b)  (c)  W
"   (CH3CH2CH2CH2S)3-P
en
                                                                                                          T    J
                                                                                                  a    9.08   7


                                                                                                  b,c   8J-&8


                                                                                                  d    7.2
                                                                                            10

-------
A-49
                  a
                  b
                  c
                  d
9.05
8.5
8JZ5
7.01
                            6.5
                           IS(P-H)

-------
                                              (d),
         W*p»yn
ui
                                 CH3'
                                        O
                                  (a)
                (b)
                                                  (d)
NH2
 (b)
                                                                                             A-50
                                                                  a

                                                                  b

                                                                  c

                                                                  d
7.24    10.5

3.14

2.61

1.98
                                                                                                        10

-------
THE DDT-TYPE COMPOUNDS
Most DET-type compounds contain para-disubstituted benzene rings whose
protons produce complex multiplets.  Each benzene ring contains four
magnetically non-equivalent protons that form two pairs of equivalent
nuclei with a chemical shift difference approximately equal to the
coupling constants involved.  This is defined as an AA'BB1 system (6).
The complex spectrum prevents interpretation by visual inspection, but
an approximation of the ortho coupling constants and aromatic proton
chemical shifts was obtained as described in a previous publication (4).
The ortho protons of compounds with the CGI, moiety on the ct-carbon
resonate at a significantly lower field (r2.42-2.52) than ortho protons
of compounds with other functional groups on the a-carbon 02.72-2.90).
This large deshielding effect of the CC13 moiety may be explained by
considering the molecular stereochemistry as observed in Leybold models.
When three chlorines are substituted on the 8-carbon, the ortho aromatic
protons cannot escape the deshielding effect of the chlorine atoms.
However, if only one chlorine atom is removed, the ortho protons are no
longer forced into close proximity to the chlorine atoms.  The deshielding
effect of the CC1  group is greatest when chlorine substitution on
one of the aromatic rings occurs in the ortho position.  Examination
of a I^ybold model shows that a chlorine in the ortho position of a ring
causes rotation of that ring around the aromatic-aliphatic C-C bond to
be energetically unfavorable.  The most favorable conformation places the
remaining ortho proton near the B-carbon chlorines and the ortho chlorine
as far as possible from the CCLj moiety.

The meta protons of the aromatic rings with para chlorine substi-
tuents resonate in a range from t2.68-2.76.  As expected, the benzylic

                              61

-------
proton signals  05.06-6.0) are deshielded more by  an  ortho  than  a para
chlorine on an aromatic ring.
Technical DDT is a mixture of p_,p_f-DDT and  o.p^-DDT.   Peak  area  measure-
ments by electronic integration of the part of the spectrum containing
the signals of the benzylic protons  (p_,p_'-DDT, iS.OO; p_,p_'-DDT,  x4.25)
provide the isomeric composition of  the  sample  (80% p_,p_'-DDT,  201 £,p_'-DDT)'
The spectrum of Dilan, a mixture of  Bulan and ProIan, contains only one
benzylic peak but has two methyl signals with significantly different
chemical shifts (triplet, i9.ll; doublet, T8.54).   The integration  of these
methyl signals provides the percentage of each compound in  the mixture
(62% Bulan, 381 Prolan).
                               62

-------
             (a)
                              (b)  (c)
                                       CCI3(«)  (W
                                                        B-l
                                                                          a     SJOQ
                                                                          b     2.77   as
                                                                          «     W3   8.5
.   4
                                                                 10

-------
                                           B-2
(0  («)   CCI3«   (b)
                                                              a    4.25
                                                              b    2.74   8.5
                                                              c   2.6-2.9
                                                              d    2.52   8.5
                                                              •    1.88
                                                    10

-------
B-3
               Technical DDT
                Mixture of
                  o,p' DDT
                    and

-------
                                                          B-4
\r"iiuni1^T^rtn»)»ljmn>|i M. rv A or. 'i	r
                                                                              a   428
                                                                              b   2.4-24
                                                                              c  L84H.96
                                                                  10

-------
                                                                                        B-5
    Mvthoxychlor
o\
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                                                  (b)
                                                                        W   W   CCI3W)  (c)
a
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d
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6.29
5.06
3.18   9
2.52   9
                                                                                                10

-------
                                                                                                 B-6
03
                                                                              (b)  (c)   OH (e)   (b)
                                                                     (a)
                                                                                                                   a
                                                                                                                   b
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6.48
2.76   9
2.42   9
                                                                                                          1O

-------
  sto _ _/
    p,p'DDD
                              (d)
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                                                                                                   B-7
(di  (c)
(c)   (d)
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                                      a    5.49

                                      b    3.74

                                      c    2.78

                                      d    2.74
                                   8

                                   8

                                   9

                                   9
                                                                                                            10

-------
B-8
a
b
c
              4*2
              3A4

-------
B-9
                 a    60S   8



                 b    5.75   8



                 c    2.88   8.5



                 d    2.74   &5
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-------
                                                                                                B-10
      P«rthan«
   50
ro
                               (f)
                           J
                                 W
                                                  <•)   (f)   H   <«
                                                  {•)   (OCI-C-CKO  (e)
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                                                        I
8.84
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5.50
3.68
2.92
230
                                                                                                                             9
                                                                                                                             9
                                                                                                        10

-------
DDE
                   (b)
(a)
                                              (b)
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                                                                                                     T_    J
                                                                                                a   ZA8    9
                                                                                                b   2.75    9
                                                                                       10

-------
B-12

                   a
                   b
                   c
                   d
_L    .i
3.45
2.91    8^
2.77    8^
2.75    8.5
2.65    8.5
          10

-------
B-13
                  a
                  b
                  c
 3.62
 3.28
2.5-3JO

-------
DDNU
                      (clb)
                                        (a)
                                                       W  (W
(b)  (c)
                                                 Cl-
       -Cl
                                                                                   B-14
                                                                                                          x
                                                                                                      a   4.59
                                                                                                      b   2.80
                                                                                                      e   2.74
                                            9

                                            9
                                                                                            10

-------
B-15
                a
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2J5
2.29
                         8.5
         10

-------
                                                                                                    B-16
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                                                                                                                                   9
                                                                                                              10

-------
                                                                                         B-17
ite
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                         (d)
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                                                                     (d)   (0
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a   6.29
b   5.06
c   279
d   2.73
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-------
                                                                                        B-18
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-------
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                                                                                                  B-22b
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A  H0*Hd d««wpl*d
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-------
B-23
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                Prolcm and Bulan

-------
                                                                                    B-24a
     DDOH
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-------
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4°
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                                                                                  (•)   (d)  <4  (d)  (•)
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                                                                                                                            a   8.19

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                                                                                                                            d   2.97    9
                                                                                                                    10

-------
                                                                                                 B-25
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00
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c    
-------
B-26
                  T
                a  6.24
                b  5.82
                e  4.57
                d  2.77

-------
                                                                        B-27
Isebutyl Triph«nftm*thylamin«
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                                   (a)    «   (a)
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a  9.11  7

b  8.54

C  8.33

d  8.05  6

-------
THE CARBAMATE PESTICIDES
Thirteen carhamate pesticides included in this study have the general
structure:
                          0    H
                          II  /
                      R-O-C-N
                             \
In all cases, the methyl protons resonate in a narrow range from
T?. 20-7. 29 and produce a doublet ( J = 5 Hz) due to coupling of the methyl
protons with the amide proton.
Although hindered rotation about the N-C-0 bond of amides is quite
common and produces both the cis and trans isomers, this phenomenon
is observed at ambient temperature in only one of the N-monosubstituted
carbamates, Azak.  Other investigators (7,8) have also reported hindered
Station about the N-C^O bond in carbamates at low temperature but
essentially free rotation at higher temperatures.  In Azak, the bulky
t-butyl groups substituted on the benzene ring in the ortho positions
     sterically hinder rotation — a signal is observed for each isomeric
     at ambient temperature.  Both N,N-dimethyl carbamates included in this
study (Dimetilan and isolan) exhibit hindered rotation at ambient
temperature and produce signals for both rotomer forms.
    chemical shifts of both the NH and NQI  proton signals of Zectran
                                          •?
are dependent on solvent and concentration.  Various concentrations of
Zectran in three different solvents were used to study the effects of
solute-solute and solute -solvent association (5).

•*he signals of the protons near or adjacent to nitrogen in many of these
impounds show broadening due to the quadrupole moment of the nitrogen
                              93

-------
nucleus as well as some hindrance to rotation  (7, 9).  Increasing the
sample temperature sharpens peaks that are broadened due to one or both
effects (10, 11).  Low temperature studies (5) confirmed that rotation
is hindered in both the thiolcarbamates  (example:  sutan) and the dithio-
carbamates (example:  Vegadex).
                                   94

-------
                                                   c-i
   o
   II   W)   (c)

O-C-NH-CH3
                                                                       T   J
                                                                    a   7.91



                                                                    b   7.76


                                                                    e   7.26



                                                                    d   4.7



                                                                    e   3.25
                                                           10

-------
                            C-2
   ft   (d)   (b)
O-C-NH-CH
                                               a  8.77

                                               b  7.26

                                               c  7.12

                                               d  4.6

                                               e  2A-&2
7

S

7

-------
C-3
                        &64



                        7.65



                        7.22



                        7.06



                    d'   4.8



                    d    4.4



                    e    2J8
a


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                               W
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                              (4

-------
                                                                              C-4
    Rf 5305
00
                     (b)
                         (c)    (a)
                  
-------
                                                                          C-5
    Baygon
vo
                           II  (d)  (b)
                        O-C-NH-CHo
                            (c)      3
                        O-CH-CHo
                           i    (or
                           CH3
                             J
a   a/0


b   7.22

c   5.52


d   4.6


e  2.7-12
6


5


6

-------
      Carbanolot*
o
o
                           (e) (d)
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                                                                  (b)
                                           (c)
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                                                                                                   b
                                                                                                   d

                                                                                                   e
7.83


7.20



4.70



3.07


2.87
                                                                                           10

-------
                                                                            C-7
Bcnomyl
         {}  (8)   (<)    (b)   (b)   (a)
         C-NH-CH2-CH2-CH2-CH3


           X-NH-C-O-CHo
         N'    (h) JJ     (d)
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      a  9.02

      b  8.2-8.7

      e  6.57

      d  6.20

       •  2.80

       f  1.66

       g -0.14

       h - 1.4
                                                                                                     7(Hb-Hc)
                                                                                                     6(Mc-Hg)
                                                                                     10

-------
                                                                                       C-8
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    Mvtabolit*  o*400B«nomyl i«
                                      .300
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M      °
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                                                                                                        a  6.30


                                                                                                        b  6.19


                                                                                                        e  3.40   8.5(HC-H«)
                                                                                                                 2.5(Hc-Hd)
                                                                                                        d  3.12   2.5(He-Hj)

                                                                                                         e  2.76   4.5(Hc-He)

-------
                                                                                 C-9
    S«vin
o
OJ
              O
              II  (b)   (a)

           O-C-NH-CH3
                                          (b)
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                                                                                  ^
a   7.29


b   4.7


c  2.0-2.8
                                                                                          10

-------
C-10
                  a   8.24
                  b   7.38
                  <   7.2
                  d   7.24   5
                  e   4.7
                  f   19-3.2

-------
C-ll
                 a   8.52



                 b   7.20



                 c   7.00



                 d   4.7



                 e  3.0-33

-------
                               C-12
      (b)  (a)
O-C-NH-CHo
                                               a  7.32
                                               b  4.59
                                               e  2.3-3.0

-------
                                                                        C-13
Matacil
                     o-C-NH-CH
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                                   (d)
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                                                                                        a   7.71




                                                                                        b   7,37



                                                                                        c   726




                                                                                        d   4.6



                                                                                        e   3.1
                                                                                10

-------
                                                                         C-14a
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7.28
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4.80
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                                                                                 10

-------
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                                                                                                   e   3.13
                                                                                          10

-------
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-------
C-17
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-------
                                                                      C-17b
Commercial  Sifmat*
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SO*  3,4 Isomer
2O*  2.3 Isomer

-------
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-------
                                                        C-19
 (b)      |  *(»)        ||   (d)   (c)
CH3-S-OCH=N-O-C-NH-CH3
                                                                        a   8.54

                                                                        b   8.03

                                                                        c   7.10   5

                                                                        d   3.75

                                                                        e   2.46

-------
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-------
                                                                  C-21
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-------
                                                                          022
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                                                                                            d   24-3.1
                                                                                   10

-------
                                                                               C-23
   CIPC
OW
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                                                                                      a  8.75
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                                                                                      d  25-3.1
6
6
                                                                                       10

-------
   Barban
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f
o
II
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                    (d)
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                                                     5.86
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-------
                                                                           C-25
  T
  150
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to
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2.4-2.9
                                                                                   10

-------
                                                                 C-26
NI
u>
     ,t-  -  _,       »  «
     W  W  <•)  N-OS-CH2CH3

    CH3CH2CH2
a
b
c
d
e
9.10
8.73
8.40
7.11
6.72
7
7.5
7-75
7.5
75

-------
NJ
                               -  ~        X
                               CH3CH2-S-C-N
                                           S
                                                                                C-27
                                                                                  T   J
                                                                               a   9.09  &5
                                                                               b   ars   7
                                                                               c   7.96
                                                                               d   7.10   7
                                                                               •   &81  73

-------
                                                                       028
 (b)  (d)  (e)         CH2CH3
CH3CH2CH2-S-C-N
                  "cHnCHoCHoCHo
                      z          3
                                                                                        a   9.08  6J5
                                                                                        b   9,03   7
                                                                                        c   8.86   7
                                                                                        d  8.2-8.7
                                                                                        •   7.15   7
                                                                                        f   6.70   7
                                                                                        g   6.M   7

-------
                                                                                C-29
    Vcrnam
 r
tr>
       300               (e)2°° (c)  (a)
 (W  ft)  (d)     S   XCH2CH2CH3
CH3CHoCH9-S-C-Nv
                    X
                                                    (e)   (c)  (a)
                                                                    a   9.10   75

                                                                    b   *02   7

                                                                    c   &2-&6

                                                                    d    7.12   7

                                                                    e    6.71   75
                                                                                         10

-------
                                                                                 C-30
NJ
             x

         CH      °        Cl
         CHo N  ii        i
            o   N-C-S-CH2-C=CHCI
a

b   6.2

c   6.15   1-0

<'   5.96   OA

d   3.78   O6

d'   X49   iJO
                                                                                                 (c-) W1   W
                                                                                                -CH2 ,H   -CHj Cl
                                                                                                 c=c     c=c
                                                                                                Cl  Cl   c'l  H
                                                                                         10

-------
                                                                        C-31
  * Avod.x BW
    CHo. (b)
        CH
oo
                   ,-,
          N-C-S-CH0-C=C
     (a)
                          Cl
        '  (b)
                                                   (b)
a
b
c
L  i.
&71   7
63
&90
                                                                                1O

-------
                                                                           C-32
    Ro-N«*t
     (b)  (d)     ]f   xCH2CH3
    CH3CH2-S-C-N
to
vo
a
b
c
d
e
I
8.82  7
8.72  7
8.1-8.9
7.10  7
6.68  7
6.2
                                                                                   10

-------
033
                      a
                      b
                      c
                      d
8.72   7.5
8-2-8J
7.09   Z5
6.5

-------
           C-34a
O=C    C-OCHo
0  \   //     J
                           I
                        a 6.29
                        b 5.99
                        c 4.82
J.
IS

16

-------
       2.0
3.0
                                  4.0
5.0   PPM(T)    6.0
                           7.0
8.0
  C-34b
9.0            lb
  Jo   Suprocide
U)
NJ
       8.0
                    7.0
                                                              (9)
                                               300
                                                                      200
              6.0
5.0   'PPM(i)'   4.0
                                                                           3.0
0
* 6O MHz
_^_™__j
i i.i
(b
A
1
. . . 1 ......... 1 - ... . .... 1 .... 	 	 	
>
'U

L 1
^^^^l^^ffrtymMfW'^Jfr-t^'lj ttfot tyt&iffl^f^f^ j^f1 Vf^T^l^rf' ^^VMff^^V^W^^fl>^^lUu^^<
1 1 . 1 . . 1 .... 1 ,
. ... 1 .... 1 .... 1 . 	 1 	 1 ... - ^- i '-—'
                                                                    2.0
                                                       1.0

-------
                                                                C-35
    Thirom
           n      S
        N-C-S-S-C-N
                     CH
U)
u>
                                                                       10
                                                                                 6.40

-------
I
T  V.gad.x
                                 (b)
                                      •5-C
                                      25*C
                                      amb*
                                    ,60'C
                                                                           tt
                                                                             60'C
                                                                                           C-36
           S        w  ,   ,

     «»>  (b)  N-C-S-CHo-CsC

           X          ^    V
                                                                                        a   R72



                                                                                        b   6.12



                                                                                        c   5.72



                                                                                        d   4.73



                                                                                        
-------
         C-37
(b)
£
H2
W)
(o)
                           a

                           b
                           c

                           d
                                       7.28

                                       6.49

                                       5.59
                  10

-------
                             SECTION IV


                          INDEX TO SPECTRA
 AbateR -  A-19
                                D
 Acaralate  -  see Chloropropylate

 Alkron  -  see Ethyl  Parathion
        D
 Aileron - see  Ethyl Parathion
                       R
 Aminocarb  -  see Matacil
       j^
 Anofex  -  see p_,pJ-DDT
                     T>
 Aprocarb - see  Baygon
                      1^
 Arpocarb - see  Matacil

 Aspon  -  A-46
       R            R
 Asuntol  - see  Co-Ral
       R
 Avadex  -  C-30

 Avadex BW  -  C-31

 Azak - C-3
                                 R
 Azinphosethyl -  see  Ethyl Guthion
                            j^
 Azinphosmethyl  - see Guthion

 AzodrinR - A-10
Banol - see Carbanolate

Barban - C-24
       n
Basudin  - see Diazinon
      n
Baygon  - C-5
      n
Baytex  - see Tiguvon
       j^
Benlate  - see Benomyl

Benonyl - C-7

Benonyl metabolite - C-8
                                 137

-------
Bidrin  - A-ll
Bladafume - see Sulfotepp
     R
Bulan  - B-22
Carbanolate - C-6
                    j^
Carbaryl - see Sevin
                      j^
Carbicron - see Bidrin
                        j^
Carbofuran - see Furadan
                              R
Carbophenothion - see Trithion
Carbophos - see Malathion
       R
Carbyne  - see Barban
                  j^
(DEC - see Vegadex
Chem-Hoe - see IPC
Chlorobenzilate - B-19
Chloro-IPC - see CIPC
Chloropham - See CIPC
               £
Chloropropylate  - B-20
CiodrinR - A-9
CIPC - C-23
Co-RalR - A-40
Corothion - see Ethyl Parathion
                      R
Coumaphos - see Co-Ral
     R
Cygon  - A-3
Cygon oxygen analog - see Dimethoxon
Cynem - see Zinophos
      - see Methyl Parathion
DATC - see Avadex
Dazomet - see Myrlone
                             138

-------
  DBF -  B-15
                       j^
  2,3 DCDT - see  Avadex
  DBA -  B-16
  DDA Methyl Ester  - B-17
  o,£'-DDD - B-8
 £,2.'-ODD - B-7
 DDE  -  B-ll
 DBMS - B-9
 o,£'-DDMU  - B-13
 £,£'-DDMU - B-12
 DDNU - B-14
 DDQH - B-24
 o,£' -DDT - B-2
 £,£'-DDT - B-l
 DDT acetal - B-26
 DDT, Techical -  B-3
 DDVP -  A-8
 DEFR -  A-49
 Dedevap - see DDVP
 DeGreen - see DEF1*
 Deleaf  Defoliant - see  Merphos
      R
 Delnav   - A-31
                      j^
Demeton 0 -  see  Systox
Demetron  S  - see Iso-Systox
2,4-DEP - see  Falone
                     j^
Diallate  - see Avadex
Diazinon - A-37
                             139

-------
Diazinon oxygen  analog -  see  Diazoxon

Diazoxon - A-38
      R
Dibrom  - A-6
        R
Dicaptan  - see  Dicapthon

Dicapthon - A-24
                                    n
Dichlorophen (e)  - see Preventol  GD

Dichlorvos - see DDVP
                       1^
Dicofol - see Kelthane
     R
Dilan  - B-23
        p
Dimecron  - see  Phosphamidon
                       R
Dimethoate - see Cygon

Dimethoxon - A-4

Dimethoxy DET -  see Methoxychlor

DimetilanR - C-21
        j^
Dinocide  - see p_,p_'-DDT
                        n
Dioxathion - see  Delnav

Diphenamid - B-18
                       R
Dipteres - see Neguvon
                       j^
Dipterex - see Neguvon
                          R
Disulfoton - see  Di-Syston
         j^
Di-Syston  - A-28
                              n
Dithiodemeton -  see Di-Syston
        j^
Dithione  - see  Sulfotepp
            j^
Dithiosystox  -  see Di-Syston

DMDT - see Methoxychlor
                  R
DMPA - see Zytron
                  R
DMTT - see Mylone
               R
DNB - see Bulan
                             140

-------
                R
UNP - see Prolan
         R              R
Dowco-139  - see Zectran
        R             R
Dow 1329  - see Zytron
Dow ET-14  - see Ronnel (technical)
         R
Dow ET-57  - see Ronnel (purified)
                   R
DTMC - see Kelthane
Dursban  - A-35
Dupont Fungicide 1991 - see Benomyl
Dupont Fungicide 1991 metabolite - see Benomyl metabolite
Dylox  - see Neguvon
Dymid  - see Diphenamid

E-605 - see Ethyl Parathion
Easy Off-D - see Merphos
Enide - see Diphenamid
                        R
ENT 24, 969 - see Supona
     R
Entex  - see Tiguvon
EPN - A-44
EPN-300  - see EPN
     R
Eptam  - C-26
EPTC - see Eptam
Ethion - A-33
             R
Ethyl Guthion  - A-39
Ethyl Parathion - A-41
Etilon - see Ethyl Parathion

Falodin - see Falone
Falone - A-47
Far-Go - see Avadex Bto
                            141

-------
 Fendilorphos - see Ronnel
 Fenthion - see Tiguvon
      R
 Folex  - see Merphos
        R
 Folidol  - see Ethyl Parathion
 Folidol M - see Methyl Parathion
          R                R
 Folithion  - see Sumithion
 Forte - see Thiram
           R            R
 Fostion MM  - see Cygon
          R                R
 Frumin AL  - see Di-Syston
        J*                R
 Frumin G  - see Di-Syston
        U
 Furadan  -  C-ll
   R                   R
G-4  - see Preventol GD
Gardentox - see Diazinon
       P
Gardona  - A-21
Garrathion - see Trithion
                    R
GC-4072 - see Supona
Genitox - see p_,p_'-DDT
       R
Gesapon  - see
Gesarex  - see £,p_'-DDT
       R
Gesarol  - see p^pJ-DDT
        R
Guesapon  - see p^pJ
Guesarol - see p_,£'-DDT
         R
Gusathion  - see Guthion
           R                    R
Gusathion A  - see Ethyl Guthion
GuthionR - A- 15
Guthion oxygen analog - A- 16
     j^
Gyron  - see p_,p_'-DDT
                                 142

-------
 Herkol - see DDVP
       R             R
 Hydram  - see Ordram
       R
 Imidan  - A-17
 INPC - see IPC
 IPC - C-22
 Isobutyl Triphenylmethylamine - B-27
 Isolan - C-20
                    R
 Isomeric Chlorthion  - see Dicapthon
 Iso PPC - see IPC
 Iso-SystoxR - A-30
       R
 Ixodex  - see p_,£f-DDT

 Karbofos - see Malathion
 KelthaneR - B-6
       R
 Korlan  - see Ronnel

 Landrin - see SD-8530
        j^
 Lannate  - see Methomyl
         R
 Lebaycid  - see Tiguvon

Mafu  -  see DDVP
Malaoxon - A-2
Malaspray -  see Malathion
Malathion  - A-l
Malathion  oxygen analog  - see Malaoxon
Malathon  -  see  Malathion
Marlate  -  see Methoxychlor
Matacil  - C-13
MCA-600 -  see Mobam
                                 143

-------
o-MDT - B-4

Mercaptophos - see Tiguvon
                               R
Mercapto dimsthur - see Mesurol

Merphos - A-48

MesurolR - C-15
                                          j^
Metaisosystoxsulfoxide - see Meta-Systox-R
             R
Meta-Systox-R  - A-5

Methomyl - C-18

Methoxychlor - B-5

Nfethoxy DDT - see Methoxychlor
                                               K
Methyl demeton-0-sulfoxide -  see  Meta-Systox-R

              R               R
Methyl Guthion   -  see Guthion

Methyl Parathion -  A-22

Methyl Trithion -  A-14
                             R
 Metmercapturon - see Mesurol

 Matron - see Methyl Parathion

 Mevinphos - see Phosdrin
                       j^
 Microfume - see Mylone
         j^
 Mintacol  - see Paraoxon

 Mobara - C-12
                      R
 Molinate - see Ordram
         R             R
 Muscatox  - see Co-Ral
        R
 Mylone - C-37

                   n
 Naled - see Dibrom

 Nankor  - see Ronnel
         R
 Navadel  - see  Delnav
         R
 Neguvon  - A-7
                                144

-------
 Nemafos  - see  Zinophos
 Nemaphos - see Zinophos
 Neocid   - see  p_,p_'-DDT
 Neocidol - see p_,pJ-DDT
 Niagara 1240   - see Ethion
 Nialate  - see Ethion
 Niran  - see Ethyl Parathion
 Nitrostigmine  - see Ethyl Parathion
 Nitrox • see Methyl Parathion
 Nitrox 80 - see Methyl Parathion
 Nogos -  see DDVP
         R
 Nomersan  - see Thiram
                       D
 Nuvacren -  see Azodrin

 Oko - see DDVP
 Ordram  - C-33
 Orthophos -  see Ethyl  Parathion
 Oxydemetonmethyl  -  see Meta-Systox-R

 Paraoxon  - A-42
 Parathion - see Ethyl  Parathion
 Parathion Methyl  -  see Methyl Parathion
 Parathion oxygen analog - see Paraoxon
 PEBC  - see TillamR
                     n
 Pebulate - see  Tillam
 Pentachlorin -  see £,p_f-DDT
 Perfekthion - see Cygon
 Perthane  - B-10
 Phencapton - A-34
Phenkaptone  - see Phencapton
                              145

-------
                    R
Phorate - see Thimet

Phosdrin - A-12

Phosphamidon - A-13

Polyram-Ultra - see Thiram
       R
Pomasol  - see Thiram
                            R
Preventol - see Preventol GD
            R
Preventol GD  - B-25
             R
Preventol GDC  - see Preventol GD


Primin  - see Isolan
      R
Prolan   - B-21
                    R
Prolate - see Inddan

Propham - see IPC
                     R
Propoxur -  see Baygon


         R
Queletox  - see  Tiguvon



 RE-5305 - C-4

 Resitox - see Co-Ral
          R
 Rhodiatox  - see Ethyl Parathion

         R
 Rhothane  - p,p'-DDD
      R            R
 Rogor  - see Cygon

 Ro-Neet - C-32

 Ronnel - A-20

        R
 Rowmate  - see Sirmate

 Roxion - see Cygon
        R
 Ruelene  - A-25
  S-847  -  see Barban
                      R
  SB-7859 - see Supona
                                   146

-------
  SD-8530 - C-l
       R
  Sevin  - C-9
  Sirmate - mixture of 2,3-and 3,4-Sirmate
  Sirmate,2,3,isomer - C-16
  Sinuate,3^4 isomer - C-17
  Sok - see Carbanolate
          R                R
  Solvirex  -  see Di-Syston
  Spectracide  -  see Diazinon
  Sulfatepp -  see Sulfotepp
  Sulfotepp  -  A-45
          R
  Sumithion  - A-23
       R
  Supona  - A-4 3
          R
  Supracide  - C-34
 Sutan - C-27
 Swep - C-25
       R
 Systox  - A-29

 IDE - see £,p_'-DDD
 TEDTP - see Sulfotepp
      R
 Temik  -  C-19
 Terbutol  -  see  Azak
       R
 Thimet  - A-2 7
                             £
 Thiodemeton 0 -  see Di-Syston
                             H
 Thiol-Systox  -  see Iso-Systox
 Thionazin - see  Zinophos
                           n
 Thiono-Systox -  see Systox
        R
Thiophos  - see Ethyl Parathion
Thiotepp - see Sulfotepp
                                    147

-------
Thiram - C-35

Tiguvon - A-18
      R
Tillam  - C-28

1MTD - see Thiram

TMTDS - see Thiram

Triallate - see Avadex BW
                          R
Trichlorofon - see Neguvon
        R
Trithion  - A-32
       R
Trolene  - see Ronnel

Tuads • see Thiram
     R              R
Tugon  - see Neguvon


UC-8454 - C-10

UC-10854 - C-2
     R             R
Unden  - see Baygon

      R
Vapona  - see DDVP
       R
Vegadex  - C-36
      R
Vernam  - C-29
                      R
Vernolate - See Vernam
       R
Viozene  - see Ronnel
      R             R
Wepsin  - see Wepsyn
      j^
Wepsyn  - A- 50
Zectran  - C-14

Zinophos - A- 36
      R
Zytron  - A-26
                                    148

-------
                            SECTION V

                         ACKNOWLEDGMENTS
Ann L. Alford and Lawrence H. Keith performed the experimental work,
interpreted the spectra, and prepared the spectral catalog.  Arthur
W. Garrison's advice and assistance with the organophosphorus and DDT
pesticide spectra are gratefully acknowledged.

The authors wish to express their appreciation to the suppliers of
the pesticide analytical standards, and in particular to James D.
McKinney, National Institute of Environmental Health Sciences, Research
Triangle Park, North Carolina; Candace Plato, Pesticide Reference
Standards Section, Food and Drug Administration, Washington, D. C.;
and John A. Gardiner, Agricultural Chemicals Research, Industrial
and Biochemicals Departments, E. I. DuPont de Nemours and Company,
Wilmington, Delaware, for the samples of several pesticides and metabolites
not commercially available.
                                 149

-------
                             SECTION VI





                             REFERENCES





 1.  For a summarizing reference see:



     L. H. Keith and A. L. Alford, J. Assoc. Offic. Anal. Ghenu, 53,



     1018 (1970).





 2.  L. H. Keith, A. W. Garrison, and A. L. Alford, J. Assoc. Offic.



     Anal. Chem., 5^, 1063 (1968).





 3.  L. H. Keith and A. L. Alford, Anal. Chim. Acta, 44, 447  (1969).





 4.  L. H. Keith, A. L. Alford, and A. W. Garrison, J. Assoc. Offic.



     Anal. Chem., 5£, 1074 (1969).





 5.  L. H. Keith and A. L. Alford, J. Assoc. Offic. Anal. Chem., £3,



     157 (1970).





 6.  J. W. Emsley, J. Feeney, and L. H. Sutcliffe, "High Resolution



     Nuclear Magnetic Resonance Spectroscopy," Vol. 1, Pergamon Press,



     London, 1965, p. 399ff.





 7.  T. M. Valega, J. Org. Chem., 31, 1150 (1966).





 8.  E. Lustig, W. R. Benson, and N. Duy, J. Org. Chem., 32_,  850 (1967).





 9.  J. L. Richards, D. S. Tarbell, and E. H. Hoffmeister, Tetrahedron 24,



     6485 (1968).





10.  J. D. Roberts, J. Amer. Chem. Soc., 78, 4495 (1956).
                                  151

-------
11.  J. W. Emsley, J.  Feeney, and L.  H.  Sutcliffe,  "High Resolution
     Nuclear Magnetic Resonance Spectroscopy," Vol.  2, Pergamon Press,
     London, 1966, p.  819.
                                    152

-------
                           SECTION VII
              PUBLICATIONS RESULTING FROM THIS WDRK
1.  L. H. Keith, A. W. Garrison, and A. L. Alford, "The High
    Resolution NMR Spectra of Pesticides. I. Organophosphorus Pesticides,"
    J. Assoc. Offic. Anal. Chem., 51, (5), 1063 (1968).
2.  L. H. Keith and A. L. Alford, "Supplementaiy Interpretations of the
    NMR Spectra of Phosphorus Pesticides,"  Anal.  (Mm. Act a, 44,
    447 (1969).
3.  L. H. Keith, A. L. Alford, and A. W. Garrison, "The High Resolution
    NMR Spectra of Pesticides. II. The DDT Class," J. Assoc. Qffic.
    Anal. Chem., 5£, 1074 (1969).
4.  L. H. Keith and A. L. Alford, "The High Resolution NMR Spectra of
    Pesticides. III. The Carbamates," J. Assoc. Offic. Anal. Chem., 53_,
    157 (1970).
5.  L. H. Keith and A. L. Alford, "Review of Nuclear Magnetic Resonance
    Spectroscopy in Pesticide Analysis," J. Assoc. Offic.  Anal.  Chem.,
    53, 1018 (1970).
                                 153

-------
en
                                                      SECTION VIII



                                APPENDIX:  CHEMICAL NAMES AND SOURCES OF THE PESTICIDES
Spectrum
No.
A-l
A-2
A-3
A-4
A-5
A-6
A-7
A-8
A-9
A-10
A-ll
Common or
Trade Name
Malathion
Malaoxon
Cygon
Dimethoxon
n
Meta-Systox-R
Dibrom
Neguvon
DDVP
Ciodrin
n
Azodrin
Bidrin
Chemical Name
0 ,0-Diirethyl S- (1 , 2-dicarboethoxyethyl)
phosphorodithioate
0,0-Dimethyl S-(l, 2-dicarboethoxyethyl)
phosphorothioate
0,0-Dimethyl S- (N-methylcarbamoylmethyl)
phosphorodithioate
0,0-Dimethyl S- (N-methylcarbamoylmethyl)
phosphorothioate
0,0-Dimethyl S- [2- (ethylsulfinyl) ethyl]
phosphorothioate
0,0-Dimethyl 0~l,2-dibromo-2,2-
dichloroethyl phosphate
0,0-Dimethyl (l-hydroxy-2,2,2-
trichloroethyl) phosphonate
0,0-Dimethyl 0-2,2-dichlorovinyl
phosphate
« -Methylbenzyl 3- (dimethoxyphosphinyloxy) t-
cis-crotonate
3- (Dimethoxyphosphinyloxy)-N-methyl-
cis-crotonamide
3- (Dimethoxylphosphinyloxy) -N,N-dimethyl-
Source
American Cyanamid
American Cyanamid
American Cyanamid
American Cyanamid
Chemagro Corp
Chevron Chem Co
Chemagro Corp
Shell Development Corp
Shell Development Corp
Shell Development Corp
Shell Development Corp
                                            cis-crotonamide

-------
in
cn
Spectrum
No.
A-12

A-13

A-14
A-15

A-16

A-17


A-18


A-19

A-20


A-21

A-22


A-23
Common or
Trade Name
PhosdrinR

Phosphamidon

Methyl TrithionR
GuthionR

Guthion oxygen
analog
Imidan

R
Tiguvon

R
Abate

Ronnel

R
Gardona

Methyl parathion

R
Sumithion
Chemical Name
0 ,0-Dimethyl 0- (2 -carbomethoxy- 1-
methylvinyl) phosphate
0,0-Dimethyl 0- [2-chloro-2- (N,N-diethyl
carbamoyl) - 1-methyl vinyl ] phosphate
0 ,0-Dimethyl S- (p_-chlorophenylthio) methyl
phosphorodithioate
0,0-Dimethyl S- [4-oxo-l ,2 ,3-benzotriazin-
3(4H)-yl methyl] phosphorodithioate
0,0-Dimethyl S- [4-oxo-l ,2 ,3-benzotriazin-
3(4H)-yl methyl] phosphorothioate
0,0-Dimethyl S-phthalimidomethyl
phosphorodithioate

0,0-Dimethyl 0- [4- (methylthio-m-tolyl]
phosphorothioate

0,0,0' ,0' -Tetramethyl 0,0'-thiodi-p_-
phenylene phosphorothioate
0,0-Dimethyl 0-{2,4,5-trichlorophenyl)
phosphorothioate

vinyl dimethyl ester 2-chloro-l-(2,4,5-
trichlorophenyl) phosphoric acid
0,0-Dimethyl 0- (4-nitrophenyl)
phosphorothioate

0,0-dimethyl 0- (4-nitro-m-tolyl)
Source
FDA

Chevron Chem Co

Stauffer Chem Co
Chemagro Corp

Chemagro Corp

Stauffer Chem Co


Chemagro Corp


American Cyanamid

Dow Chem Co


Shell Development Corp

Monsanto Chem Co


Chemagro Corp
                                              phosphorothioate

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tn
Spectrum
No.
A-24

A-25


A-26


A-27

A-28

A-29

A-30

A-31

A-32

A- 33

A-34


A-35
Common or
Trade Name
Dicapthon

Ruelene

R
Zytron

R
Thimet

Di-Syston

Systox

Iso-Systox

DelnavR

TrithionR

Ethion

Phenacapton

R
Dursban
Chemical Name
0 ,0-Dimethyl 0- (2- chloro- 4-nitrophenyl)
phosphorothioate
4-t-Butyl-2-chlorophenyl methyl
methylphosphoramidate

2,4-Dichlorophenyl methyl isopropyl-
phosphoramidothioate

0,0-Diethyl S- (ethylthio) methyl
phosphorodithioate
0,0-Diethyl S- 2- (ethylthio) ethyl
phosphorodithioate
0,0-Diethyl 0-2- (ethylthio) ethyl
phosphorothioate
0,0-Diethyl S-2- (ethylthio) ethyl
phosphorothioate
2 , 3-p-Dioxanedithiol S,S' -bis (0 ,0-
diethyl phosphorodithioate)
0 ,0-Diethyl S- (4- chloropheny Ithiomethy 1)
phosphorodithioate
0,0,0', O'-Tetraethyl S,Sf-methylene
bis-phosphorodithioate
0 ,0-Diethyl S- (2 , 5-dichloropheny Ithio)
methyl phosphorodithioate

0,0-Diethyl 0- (3 , 5 ,6- trichloro-2-pyridyl)
Source
American Cyanamid

Dow Chemical Co


Dow Chemical Co


American Cyanamid

Chemagro Corporation

Chemagro Corporation

Chemagro Corporation

Hercules Powder Company

Stauf fer Chemical Co

Niagara Chem Div, FMC Corp

Geigy Chemical Corporation


Dow Chemical Co
                                             phosphorothioate

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en
oo
Spectrum
No.
A-36
A- 37
A- 38
A- 39
Common or
Trade Name
Zinophos
Diazinon
Diazoxon
Ethyl Guthion
Chemical Name
0,0-Diethyl 0-2-pyrazinyl
phosphorothioate
0,0-Diethyl 0- (2- isopropyl-4-methyl-6-
pyrimidyl) phosphorothioate
0,0-Diethyl 0- (2-isopropyl-4-msthyl-6-
pyrimidyl) phosphate
0,0-Diethyl S- [4-oxo-l,2,3-benzo-
Source
American Cyanamid
Geigy Chemical Corp
Geigy Chemical Corp
Chemagro Corporation
A-40


A-41


A-42

A-43


A-44


A-45

A-46

A-47

A-48
      R
Co-Ral


Ethyl parathion


Paraoxon
      R
Supona


EPN


Sulfotepp

Aspon

Falone

Merphos
triazin-3-(4H)yl methyl]
phosphorodithioate

0,0-Diethyl 0-(3-chloro-4-methyl-2-oxo-
2H-l-benzopyran-7-yl) phosphorothioate

0,0-Diethyl 0-4-nitrophenyl phosphoro-
thioate

0,0-Diethyl 0-4-nitrophenyl phosphate

0,0-Diethyl-1-(2,4-dichlorophenyl)-2-
chlorovinyl phosphate

0-Ethyl 0-4-nitrophenyl phenylphosphono-
thioate

0,0,0' jO'-Tetraethyl dithiopyrophosphate

0,0,0' ,0'-Tetrapropyl dithiopyrophosphate

Tris-(2,4-di chlorophenoxyethy1) phosphite

Tributyl phosphorotrithioite
Chemagro Corporation


Monsanto Chemical Co


American Cyanamid

Shell Development Corp


E. I, Dupont de Nemours
and Co

Chemagro Corporation

Stauffer Chemical Co

U S Rubber

V-C Chemical Co

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<£>
Spectrum
No,
A-49
A-SO
B-l
B-2
B-3
B-4
B-S
B-6
B-7
B-8
B-9
B-10
Common or
Trade Name
DEF11
WepsynR
I^'-DDT
o,E'-DDT
Tech DDT
o-MDT
Methoxychlor
Kelthane
p_,j>'-DDD
o,p'-DDD
DDMS
Perthane
Chemical Name
S,S,S-Tributyl phosphorotxithioate
5"AminO"l-bis(diethylamido)phosphoryl-
3-phenyl- 1,2 ,4-triazole
l,l,l-Trichloro-2 ,2-bis (p_- chlorophenyl) -
ethane
1 ,1 ,!-TrichlorO"2-jV'Chlorophenyl-2-o-
chlorophenylethane "
Mixture of o,E'-DDT and g^'-DDT
1 , 1 , l-Trichloro- 2-o- chlorophenyl- 2-
phenylethane ""
l,l,l-Trichloro-2,2-bis (^-methoxyphenyl)-
ethane
1,1-bis (^-Chlorophenyl) -2 ,2 ,2-trichloro-
ethanol
l,l-Dichloro-2 ,2-bis (£- chlorophenyl)
ethane
l,l-Dichloro-2-£-chlorophenyl-2-p_-
chlorophenylethane
1-Chloro- 2 , 2-bis (E- chlorophenyl)
ethane
l,l-Dichloro-2,2-bis(p-ethylphenyl)-
Source

Chemagro Corporation
Thompson-Hayward
FDA
FDA
Allied Chemical
CDC, PHS



Corp

Geigy Chemical Corp
Rohm § Haas Co
FDA
FDA
CDC, PHS
Rohm § Haas Co





                                                ethane

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       Spectrum
       No.
                Common or
                Trade Name
                      Chemical Name
                                             Source
H-
cn
o
B-ll

B-12
B-13

B-14
B-15
B-16
B-17
B-18
B-19
B-20
B-21
B-22
B-23
B-24
B-25
B-26
DDE

p^pJ-DDMLJ
o,pJ-DDMJ

DDNU
DBF
DDA
DDA methyl ester
Diphenamid
Chlorobenzilate
               R
Chloropropylate
      R
Prolan
     R
Bulan
DilanR
DDOH
         R
Preventol  GD
DDT acetal
1,l-Dichloro-2,2-bis(£-chlorophenyl)-
ethylene
l-Chloro-2,2-bis(p_-chlorophenyl)ethylene
l-Chloro-2-£-chlorophenyl-2-p_-chlorophenyl-
ethylene
1,1-bis (p_-Chlorophenyl) ethylene
p_,£f -Dichlorobenzophenone
bis (p_-Chlorophenyl) acetic acid
Methyl bis (pj-chlorophenyl) acetate
N,N-Dimethyl-2,2-diphenylacetamide
Ethyl-p_,p_' -dichlorobenzilate
Isopropyl-p_fp_f -dichlorobenzilate
2-Nitro-l, 1-bis (p_-chlorophenyl)propane
2-Nitro-l, 1-bis (p_-chlorophenyl)butane
Mixture of Prolan and Bulan
2,2-bis (p_-Chlorophenyl)ethanol
bis (£-Hydroxy-£-chlorophenyl) methane
2-bis (p_-Chlorophenyl)methyl-1,3-
dioxolane
FDA

CDC, PHS
FDA

CDC, PHS
Eastman Org Chem
CDC, PHS
CDC, PHS
Upjohn Co
Geigy Chemical Corp
Geigy Chemical Corp
Commercial Solvents Corp
Commercial Solvents Corp
Commercial Solvents Corp
CDC, PHS
General Aniline §  Film Corp
CDC, PHS

-------
Spectrum
No.
Common or
Trade Maine
Chemical Name
                                                                                   Source
B-27

C-l
C-2
C-3

C-4
C-5
C-6
C-7

C-8
C-9
C-10

C-ll

C-12
C-13
                Isobutyl triphenyl-
                methylamine
                SD 8530
                UC 10854
                    R
                Azak
                 RE  5305
                 Baygon
                 Carbanolate
                 Benomyl

                 Benomyl  metabolite
                 Sevin
                 UC 8454
                 Furadan
                        R
                 Mobam
                      R
                        R
                 Matacil
                      3,4,5 -Triraethy Ipheny 1-N-methylcarbamate
                      3-Isopropylphenyl-N-methylcarbamate
                      2,6-Di-tert-butyl-4-methylphenyl-N-
                      methylcarGainate
                      3-sec-Butylphenyl-N-methylcait>amate
                      2-Isopropoxyphenyl-N-methylcarbamate
                      3,4-Xylyl-6-chloro'N-methylcarbamate
                      Methyl l-(butylcarbamoyl)-2-benzimida-
                      zole carbamate
                      Methyl 5-hydroxy-2-benzimidazole carbamate
                      1-Naphthyl-N-methylcarbajnate
                      1- (5,6,7,8-Tetrahydro) -naphthyl-N-
                      methylcarbamate
                      7-(2,3-Dihydro-2,2-dimethyl)-
                      benzofuranyl-N-methylcarbamate
                      4-Benzothienyl-N-methylcarbamate
                      4-Dimethylamino- 3-methylphenyl-N"
                      methylcarbamate
                                             Inperial Chem Industries  LTD

                                             Shell Development Corp
                                             Union Carbide Corp
                                             Hercules  Powder Co

                                             Chevron Chemical Co
                                             Chemagro Corporation
                                             Upjohn  Company
                                             E.  I. DuPont de Nemours § Co

                                             E.  I. DuPont de Nemours § Co
                                             Union Carbide Corporation
                                             Union Carbide Corporation

                                             Niagara Chemical Div, FMC Corp

                                             Mobil Chemical Co
                                             Chemagro Corporation

-------
01
NJ
Spectrum
No.
C-14
C-15
C-16
C-17
C-18
Common or
Trade Name
1^
Zectran
MesurolR
Six-mate, 2,3-
isomer
Sirmate, 3,4-isomer
Methomyl
Chemical Name
4-Dimethylamino- 3 ,5-dimethylphenyl-
N-methy Icarb amate
4 -Methy Ithio- 3 , S - dimethylpheny 1-
N-me thy Icarb amate
2 ,3-Dichlorobenzyl-N-me thy Icarb amate
3,4-Dichlorobenzyl-N-methylcarbamate
S-Methyl N-[(methy Icarb amoyl)oxy]
Source

Dow Chemical Co
Chemagro Corporation
FDA
FDA
E. I. DuPont


de Nemours
C-19
C-20

C-21

C-22
C-23
C-24

C-25
C-26
C-27
Temik
Isolan

Dimetilan

IPC
CIPC
Barban
                                R
                       Swep
                       Eptam
                       Sutan
                            R
thioacetimidate
2-Methyl-2-methylthiopropionaldehyde-
0-methylcarbamoyl oxime
5- (1- Isopropyl- 3-methyl) -pyrazolyl-N,
N-dimethylcarbamate
3- (l-N,N-Dinethylcarbamoyl-5-methyl) -
pyrazolyl-N,N-dimethylcarbamate
Isopropyl-N-phenylcarbamate
Isopropyl-N-(3-chlorophenyl)carbamate
4-Chloro-2-butynyl-N-(3-chlorophenyl)-
carbamate
Methyl-N-(3,4-dichlorophenyl)carbamate
S-Ethyl-N ,N-dipropylthiolcarbamate
S-Ethyl-N,N-diisobutylthiolcarb amate
IMion Carbide Corp
Geigy Chemical Corp

Geigy Chemical Corp
Pittsburgh Plate Glass Co
Pittsburgh Plate Glass Co
Gulf Res § Dev Co

Niagara Chem Div, FMC Corp
Stauffer Chemical Co
Stauffer Chemical Co

-------
Spectrum
No.
C-28
C-29
C-30
Common or
Trade Name
R
Tillam
Vernam
Avadex^
Chemical Name
S-Propyl-N-butyl-N-ethyl thiolcarbamate
S-Propyl-N,N-dipropyl thiolcarbamate
S- f 2 , 3-Dichloroallyl) -N tN-diisopropyl
Source
Stauffer Chemical Co
Stauffer Chemical Co
Monsanto Chemical Co
C-31
C-35
C-36
C-37
Avadex
BW11
C-32
C-33
C-34
Ro-Neet
Ordram
Supraci
                         R
Thiram
Vegadex
      R
Mylone
       R
thiolcarbamate
S-(2,3,3-Trichloroallyl)-N,N-diisopropy 1
thiolcarbamate
S-Ethyl-N-ethyl-N-cyclohexylthiolcarbamate
S-Ethyl -hexahydroazepine-1 - carbothioate
0,0-Dimethyl-S-[2-methoxy-1,3,4-
thiadiazol-5(4H)-onyl-4-methyl]-
dithiophosphate
bis (DimethyIthiocarbamoyl) disulf ide
2-Chloroallyl-N,N-diethyl dithiocarbamate
3,5-Diroethyl-l,3,5-tetrahydrothiadiazine-
2-thione
Monsanto Chemical Co

Stauffer Chemical Co
Stauffer Chemical Co
Geigy Chemical Corp

E. I. DuPont de Nemours
Monsanto Chemical Co
Union Carbide Corp
                                                                                      Co

-------
    Ace fun ion Number
                     Subject Field & Group
                          010B
                                         SELECTED WATER RESOURCES ABSTRACTS
                                              INPUT TRANSACTION FORM
     rganization
     Water Quality Office, Environmental Protection Agency, Southeast Water
     Laboratory,  Athens, Georgia
    Title
     CATALOG OF  PESTICIDE NMR SPECTRA
1Q I Authors)
	 ' ALFORD, ANN L.
KEITH, LAWRENCE H.
16

21
Project Designation
PROJECT 116020 EWC
Note
22
   Citation
    WQO Project  #16020
    11 references
                        ,  p. 1-157, April, 1971, 114  figures, 2 tables,
23
Descriptors (Starred First)

*Pesticides, *Nuclear magnetic resonance, *0rganophosphorus pesticides,
*Carbamate pesticides, *DDT, data collections, spectroscopy
25
Identifiers (Starred First)
    *Chemical shifts,  *Coupling constants, spin decoupling
27
   Abstract
         This catalog contains the  100 MHz nuclear  magnetic resonance
    spectra of 114  organophosphorus,  DDT, and carbamate pesticides  and a
    brief discussion of their most  important features.   Chemical  shifts
    and coupling constants are shown  on each spectrum.  (Alford -  Southeast
    Water Laboratory)
      ANN L. ALFORD
                         Institution
                             SOUTHEAST WATER LABORATORY
WR-.102 (REV JULY I96»>
VVRSIC
                                    SEND TO: WATER RESOURCES SCIENTIFIC INFORMATION CENTER
                                          U.S. DEPARTMENT OF THE INTERIOR
                                          WASHINGTON. O. C. 20240

                                                                * CPO! 1988-359-339

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