TREA

Herbicidal sulfonamides

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Information

  • Patent Grant
  • 4889550
  • Patent Number
    4,889,550
  • Date Filed
    Thursday, September 1, 1988
    35 years ago
  • Date Issued
    Tuesday, December 26, 1989
    34 years ago
Information
Abstract
Novel compounds of Formula I are useful as herbicides and plant growth regulants.
Description

BACKGROUND OF THE INVENTION
EP-A-44,209 discloses herbicidal sulfonamides of formula ##STR1## wherein R is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy;
R.sub.1 is H, Cl or C.sub.1 -C.sub.4 alkyl;
R.sub.2 is H or CH.sub.3 ; and
L is, among other values, CO.sub.2 R.sub.10, CONR.sub.3 R.sub.4, CN, Cl, Br, NR.sub.3 R.sub.4, S(O).sub.n R.sub.7, SO.sub.2 NR.sub.3 R.sub.4 and OR.sub.9.
EP-A-112,803 discloses, in part, herbicidal sulfonamides of formula ##STR2##
South African Patent Application 84/2722 discloses herbicidal sulfonamides of formula ##STR3## wherein A is CR.sub.6 R.sub.7 XR.sub.8, CR.sub.9 R.sub.10 R.sub.11 or CHR.sub.7 SCQR.sub.21 ;
R.sub.9 and R.sub.10 are, among other values, H or CH.sub.3 ; and
R.sub.11 is COR.sub.24 or a C.sub.1 -C.sub.4 alkyl group substituted with, among other values, CN, NO.sub.2, OH, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkoxy, NR.sub.12 R.sub.13 and SO.sub.2 NR.sub.15 R.sub.16.
EP-A-162,723 discloses 2,5-substituted herbicidal sulfonamides of formula ##STR4## wherein R is H or CH;
R.sub.1 is C.sub.1 -C.sub.3 alkyl; and
R.sub.2 is C.sub.2 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyloxy, C.sub.3 -C.sub.6 alkenylthio, C.sub.3 -C.sub.6 alkynylthio, OCH.sub.2 CH.sub.2 OCH.sub.3, OCH.sub.2 CH.sub.2 SCH.sub.3, CH.sub.2 F, CHF.sub.2, OCF.sub.2 H, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, OCH.sub.2 CH.sub.2 Cl, C.sub.2 -C.sub.6 alkyl substituted with 1-3 atoms of F or Cl or C.sub.1 -C.sub.4 alkyl substituted with C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkylthio;
U.S. Pat. No. 4,310,346 discloses herbicidal benzensulfonylureas containing an o-sulfonamide moiety which may contain an optional floating substituent selected from F, Cl, Br, C.sub.1 -C.sub.3 alkyl, NO.sub.2, OCH.sub.3, C(O)R.sub.d, CH.sub.2 OR.sub.d, CF.sub.3, NH.sub.2, NMe.sub.2, CN, CH.sub.2 S(O).sub.n CH.sub.3, S(O).sub.n CH.sub.3, NHC(O)R.sub.d or NHCO.sub.2 R.sub.d ; wherein n is 0, 1 or 2 and R.sub.d is C.sub.1 -C.sub.3 alkyl.
U.S. Pat. No. 4,600,428 discloses N-(cyclopropylpyrimidinyl)-N-aryl-sulfonylyreas of the formula ##STR5## wherein Ar is a phenyl group ##STR6## or a naphthyl group and Q is a group X--A or R.sub.3 ;
A is alkynyl, alkyl which is unsubstituted or substituted by halogen, alkoxy, alkylthio, alkylsylfinyl, alkylsulfonyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl, or alkenyl which is unsubstituted or substituted by the substituents given above for alkyl, or A is a phenyl or benzyl group;
E is methine;
X is oxygen, sulfur, or a sulfinyl or sulfonyl bridge;
Z is oxygen or sulfur;
R.sub.1 is hydrogen, alkyl or alkoxy;
R.sub.2 is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, di-alkylamino, cycloalkyl or alkoxyalkyl, R.sub.3 is hydrogen, halogen, alkyl, alkenyl, haloalkyl, --CO--NR.sub.8 R.sub.9, --CN, --COR.sub.10, --NR.sub.1 R.sub.7 or --NR.sub.1 --COR.sub.12 ;
R.sub.4 is hydrogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, halogen, or alkoxyalkyl;
R.sub.5 is independently selected from the same groups as R.sub.3 or --X--R.sub.6 ;
R.sub.6 and R.sub.7 are each alkyl, alkenyl or alkynyl;
R.sub.8 and R.sub.9 independently of one another are each hydrogen, alkyl, alkenyl or alkynyl;
R.sub.10 is hydrogen, alkyl or haloalkyl;
R.sub.11 is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, phenyl or benzyl; and
R.sub.12 is the same as R.sub.1 but independent thereof.
South African Patent Application 84/5216 discloses herbicidal sulfonamides of formula ##STR7## in which R.sub.1 and R.sub.2 independently of one another denote hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy or (C.sub.1 -C.sub.4)-alkylthio which are optionally monosubstituted or poly-substituted by halogen, NO.sub.2, (C.sub.1 -C.sub.4)-alkoxycarbonyl, --(C.sub.1 -C.sub.4)--S(O).sub.n --, (C.sub.1 -C.sub.4 -alkyl)--N(R.sub.9 SO.sub.2 --, (C.sub.1 -C.sub.4)-alkenyloxy, (C.sub.1 -C.sub.4)-alkynyloxy, --OSO.sub.2 --(C.sub.1 -C.sub.4)-alkyl, --OSO.sub.2 CF.sub.3, --CONHR.sub.3 or --CON(R.sub.32 ;
R.sub.3 and R.sub.4 independently of one another denote hydrogen or (C.sub.1 -C.sub.4)-alkyl;
R.sub.5 denotes hydrogen, halogen, (C.sub.1 -C.sub.4)-alkylamino, di(C.sub.1 -C.sub.4)-alkylamino, (C.sub.1 -C.sub.4)-alkyl which is optionally mono-substituted or poly-substituted by halogen, (C.sub.1 -C.sub.3)-alkoxy or (C.sub.1 -C.sub.3)-alkylthio, or denotes (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-alkylthio, allyloxy or propargyloxy;
R.sub.6 and R.sub.7 independently of one another denote hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-halogenoalkyl, halogen or (C.sub.1 -C.sub.2)-alkoxy-(C.sub.1 -C.sub.2)-alkyl;
R.sub.8 denotes (C.sub.1 -C.sub.4)-alkyl, (C.sub.2 -C.sub.4)-alkenyl or benzyl;
R.sub.9 denotes (C.sub.1 -C.sub.4)-alkyl which is optionally substituted by CN or (C.sub.1 -C.sub.4)-alkoxycarbonyl, or denotes (C.sub.1 -C.sub.4)-alkoxy;
m denotes the number 1 to 3;
n denotes the number 0 to 2; and
X denotes a methine group or nitrogen.
SUMMARY OF THE INVENTION
This application pertains to novel compounds of Formula I, agriculturally suitable compositions containing them and their method-of-use as preemergent and/or postemergent herbicides or plant growth regulants. ##STR8## wherein E is CH.sub.2 or a single bond;
W is O or S;
R is H or CH.sub.3 ;
R.sub.1 is F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, OCH.sub.2 CH.sub.2 OCH.sub.3, C.sub.1 -C.sub.4 haloalkoxy, C.sub.3 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, CO.sub.2 R.sub.3, CONR.sub.4 R.sub.5, SO.sub.2 NR.sub.4 R.sub.5, SO.sub.2 N(OCH.sub.3)CH.sub.3, S(O).sub.n R.sub.6, OSO.sub.2 R.sub.7, C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, OH or C.sub.1 -C.sub.2 alkylthio, CH.sub.2 CN, C.sub.6 H.sub.5, ##STR9## R.sub.2 is CH(R.sub.16)CN, CH(R.sub.17)SCN, ##STR10## R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, ##STR11## CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 F, or C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or SCH.sub.3 ;
R.sub.4 is C.sub.1 -C.sub.3 alkyl;
R.sub.5 is H or C.sub.1 -C.sub.3 alkyl;
R.sub.4 and R.sub.5 may be taken together to form (CH.sub.2).sub.3 or (CH.sub.2).sub.4 ;
R.sub.6 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 C.tbd.CH;
R.sub.7 is C.sub.1 -C.sub.3 alkyl or N(CH.sub.3).sub.2 ;
R.sub.8 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 F, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or SCH.sub.3 or C.sub.3 -C.sub.6 cycloalkyl;
R.sub.9 is C.sub.1 -C.sub.2 alkyl;
R.sub.10 and R.sub.11 are independently C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, NHCH.sub.3 or N(CH.sub.3).sub.2 ;
R.sub.12 and R.sub.13 are independently H or C.sub.1 -C.sub.2 alkyl;
R.sub.14 is C.sub.1 -C.sub.3 alkyl;
R.sub.15 is H or CH.sub.3 ;
R.sub.16 is H, C.sub.1 -C.sub.2 alkyl or F;
R.sub.17 is H or C.sub.1 -C.sub.2 alkyl;
R.sub.18 is C.sub.1 -C.sub.2 alkyl;
R.sub.19 is H, Si(CH.sub.3).sub.3 or C.sub.1 -C.sub.2 alkyl;
R.sub.20 is H or C.sub.1 -C.sub.2 alkyl;
p is 1 or 2;
n is 0, 1, or 2;
A is ##STR12## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino;
Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, azido, cyano, ##STR13## m is 2 or 3; Q.sub.1 and Q.sub.2 are independently O or S;
R.sub.a is H or C.sub.1 -C.sub.3 alkyl;
R.sub.b and R.sub.c are independently C.sub.1 -C.sub.3 alkyl;
Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr;
Y.sub.1 is O or CH.sub.2 ;
X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H;
X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ;
Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ;
X.sub.3 is CH.sub.3 or OCH.sub.3 ;
Y.sub.3 is H or CH.sub.3 ;
X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl;
Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl;
and their agriculturally suitable salts; provided that
(1) when X is halogen, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCF.sub.2 H or N(OCH.sub.3)CH.sub.3 ;
(2) when X or Y is C.sub.1 haloalkoxy, then Z is CH;
(3) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR14## (4) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of R.sub.1 and R.sub.2 is less than or equal to six;
(5) when R.sub.2 is C(O)R.sub.17, then R.sub.1 is other than C.sub.1 -C.sub.4 haloalkyl or C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, OH or C.sub.1 -C.sub.2 alkylthio, and Y is other than cyclopropyl;
(6) when Y is C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl or C.sub.2 -C.sub.5 alkylsulfonylalkyl, then R.sub.2 is other than CH(R.sub.17)NO.sub.2 ;
(7) X.sub.4 and Y.sub.4 are not simultaneously Cl; and
(8) when R.sub.2 is C(O)R.sub.17 then R.sub.1 is other than SO.sub.2 NR.sub.4 R.sub.5 and SO.sub.2 N(OCH.sub.3)CH.sub.3.
In the above definitions, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl", denotes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers.
Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the different butoxy isomers.
Alkenyl denotes straight chain or branched alkenes, e.g., vinyl, 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.
Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl and the different butynyl isomers.
Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
The term "halogen", either alone or in compound words such as "haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be mono-halogenated or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH.sub.2 CH.sub.2 F, CF.sub.2 CF.sub.3 and CH.sub.2 CHFCl.
The total number of carbon atoms in a substituent group is indicated by the C.sub.i -C.sub.j prefix where i and j are numbers from 1 to 5. For example, C.sub.1 -C.sub.3 alkylsulfonyl would designate methylsulfonyl through propylsulfonyl, C.sub.2 alkoxyalkoxy would designate OCH.sub.2 OCH.sub.3 ; C.sub.4 alkoxyalkoxy would designate the various isomers of an alkoxy group substituted with a second alkoxy group containing a total of 4 carbon atoms, examples including OCH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3 and OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3 ; as a further example, C.sub.2 cyanoalkyl would designate CH.sub.2 CN and C.sub.3 cyanoalkyl would designate CH.sub.2 CH.sub.2 CN and CH(CN)CH.sub.3.
Preferred for reasons of increased ease of synthesis and/or greater herbicidal efficacy are:
1. Compounds of Formula I where
W is O; and
R is H;
2. Compounds of Preferred 1 where
E is a single bond;
X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2l CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; and
Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR15## Z is CH or N; 3. Compounds of Preferred 2 where
R.sub.2 is CH.sub.2 CN, CH.sub.2 N.sub.3, ##STR16## 4. Compounds of Preferred 3 where A is A-1. 5. Compounds of Preferred 4 where R.sub.1 is F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkyl substituted with 1-3 F or Cl or 1 Br, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkenyl substituted with 1-3 F or Cl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkoxy substituted with 1-3 F or Cl or 1-Br, allyloxy, propargyloxy, OC(Cl).dbd.CHCl, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2, CO.sub.2 CH.sub.2 CH.sub.2 Cl, CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3, CONH(C.sub.1 -C.sub.2 alkyl), CONCH.sub.3 (C.sub.1 -C.sub.2 alkyl), SO.sub.2 N(OCH.sub.3)CH.sub.3, SO.sub.2 NH(C.sub.1 -C.sub.2 alkyl), SO.sub.2 N(C.sub.1 -C.sub.2 alkyl).sub.2, S(O).sub.n C.sub.1 -C.sub.3 alkyl, OSO.sub.2 C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or SCH.sub.3, C.sub.6 H.sub.5 and R.sub.1 --A, R.sub.1 --B, R.sub.1 --C, R.sub.1 --D, R.sub.1 --E, R.sub.1 --F, R.sub.1 --G, R.sub.1 --H, R.sub.1 --I, R.sub.1 --J, R.sub.1 --K, R.sub.1 --L, R.sub.1 --M, R.sub.1 --N, R.sub.1 --O, R.sub.1 --P, R.sub.1 --Q R.sub.1 --R, R.sub.1 --S, R.sub.1 --T, R.sub.1 --U, R.sub.1 --V or R.sub.1 --W;
6. Compounds of Preferred 5 where
X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; and
Y is CH.sub.3, OCH.sub.3, C.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2.
7. Compounds of Preferred 6 where
R.sub.1 is F, Cl, Br, NO.sub.2, CH.sub.3, CF.sub.3 C.sub.1 -C.sub.2 alkoxy, allyloxy, OC(Cl).dbd.CHCl, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, CO.sub.2 NHCH.sub.3, CO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 NHCH.sub.3 SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 CH.sub.3, SO.sub.2 C.sub.2 H.sub.5, OSO.sub.2 CH.sub.3, OSO.sub.2 C.sub.2 H.sub.5, R.sub.1 --A, R.sub.1 --B or R.sub.1 --C.
Specifically preferred for reasons of greatest ease of synthesis and/or greatest herbicidal efficacy are:
4-(cyanomethyl)-2-[[4,6-dimethoxpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, m.p. 177.degree.-179.degree. C.; and
4-(cyanomethyl) -2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, m.p. 160.degree.-163.degree. C.
DETAILED DESCRIPTION OF THE INVENTION
Synthesis
The compounds of Formula I can be prepared from sulfonamides of Formula II and heterocyclic amines of Formula III by one or more methods described in the literature. ##STR17## Several representative routes are described below.
U.S. Pat. No. 4,394,506 (issued 7/19/83) teaches the conversion of sulfonamides to sulfonyl isocyanates and sulfonyl isothiocyanates, and their subsequent coupling with heterocyclic amines of Formula III to give sulfonylureas.
U.S. Pat. No. 4,398,939 (issued 8/16/83) teaches the formation of n-butylsulfonylureas from sulfonamides followed by phosgenation to give the sulfonyl isocyanates. Alternatively, the sulfonamides can be treated with thionyl chloride followed by phosgenation to afford the sulfonyl isocyanates. Additionally, methylcarbamate derivatives of compounds of Formula III react with sulfonamides in the presence of trimethylaluminum to give sulfonylureas.
U.S. Pat. No. 4,443,245 (issued 4/17/84) teaches two methods for the synthesis of sulfonylureas. Either a phenyl carbamate of a sulfonamide and a heterocyclic amine, or a sulfonamide and a phenyl carbamate of a heterocyclic amine couple to give a sulfonylurea in an inert solvent with base.
The preparation of sulfonamides from sulfonyl chlorides is widely reported in the literature; for reviews see: F. Hawking and J. S. Lawrence. "The Sulfonamides, " H. K. Lewis and Co., London, 1950 and E. H. Northey, "The Sulfonamides and Allied Compounds, " Reinhold Publishing Corp., New York, 1948.
Additionally, primary sulfonamides, such as those of Formula II, can be formed by removal of an N-t-butyl protecting group from the corresponding secondary sulfonamide with trifluoroacetic acid (J. D. Catt and W. L. Matier, J. Org. Chem., 39, 566 (1974)) or polyphosphoric acid (J. G. Lombardino, J. Org. Chem., 36 1971), 1843).
The requisite sulfonyl chlorides may be synthesized by known methods or with slight modifications thereof, by one skilled in the art. Several representative teachings are listed below.
Aromatic nitro groups may be transformed into sulfonyl chlorides by reduction, diazotization and coupling with sulfur dioxide/cupric chloride as taught in U.S. Pat. No. 4,310,346 (issued 1/12/82).
European Publication No. 94,821 (published 11/23/83) described the displacement of aromatic halides with thiolate anions and subsequent oxidative chlorination to yield sulfonyl chlorides.
Halogen-metal exchange of aromatic halides or proton-metal exchange of aromatics followed by quenching with sulfur dioxide gives sulfinate salts. These salts yield sulfonyl chlorides upon reaction with N-chlorosuccinimide as taught in U.S. Pat. No. 4,481,029 (issued 11/6/84). Directed proton-metal exchange of aromatic compounds has been reviewed by Gschwend and Rodriguez, Org. Reactions, 26 (1979), 1. Directed lithiation of aryl-N-t-butylsulfonamides is described by J. G. Lombardino, J. Org. Chem., 36 (1971), 1843. Also, aryllithiums may be converted directly to arylsulfonyl chlorides with sulfuryl chloride as described in S. N. Bhattacharya, et. al., J. Chem. Soc. C., (1968), 1265.
Electrophilic chlorsulfonation of an aromatic ring to give a sulfonyl chloride is well known in the literature. This technique works best for alkyl aryl ethers and alkyl aromatics. Its application is described by E. H. Huntress and F. H. Carten, J. Am. Chem. Soc., 62 (1940), 511-14 and 603-4.
Transformation of phenols to sulfonyl chlorides can be accomplished by the formation of a thiocarbamate, rearrangement, hydrolysis and oxidative chlorination as described by M. S. Newman and H. A. Kames, J. Org. Chem., 31 (1966), 3980.
Compounds of Formula II can be prepared by a variety of methods known in the literature. The most universal scheme, where benzyl halides of Formula IV are reacted with the appropriate reagent, is shown below. ##STR18## wherein U is SO.sub.2 NH.sub.2 or a previously described sulfonamide precursor, and X.sup.1 is Cl, Br or I and R.sub.2 is of the structure --CH(R.sub.17)--. Some specific methods are listed below.
NITRILES (R.sub.2 .dbd.CH(R.sub.17)CN)
Nitriles can be prepared by nucleophilic displacement of benzyl halides, usually benzyl chlorides or bromides, with potassium or sodium cyanide. Many solvents are applicable, but frequently dimethylsulfoxide is used. Thus, a benzyl bromide of formula IV can be contacted with potassium cyanide in dimethylsulfoxide for 0.5 h to 24 h at 20.degree. to 140.degree. C. For a review of this reaction, refer to Friedrich and Wallenfels, in Rappoport, "The Chemistry of the Cyano Group", pp. 77-86, Interscience Publishers, New York, 1970.
ISONITRILES (R.sub.2 .dbd.CH(R.sub.17)NC)
Heavy metal cyanides and benzylhalides react to give isonitriles. The reaction is best carried out in the dark using silver cyanide and a benzyl iodide. Typical procedures are given by A. Gautier, Ann. Chem., 142 (1867), 28 and H. L. Jackson and B. C. McKusick, Org. Syn., Col. Vol. IV, 438.
AZIDES (R.sub.2 .dbd.CH(R.sub.17)(N.sub.3)
Compounds of Formula II may be prepared by reacting an azide anion with a benzyl halide. Typically sodium azide in alcohol or wet acetone is mixed with a benzyl bromide at 20.degree.-100.degree. C. This nucleophilic displacement is reviewed in Biffin, Miller and Paul, in Patai, "The Chemistry of the Azido Group, " pp. 57-119, Interscience Pub., New York, 1971.
PHOSPHONATES (R.sub.2 .dbd.CH(R.sub.17)P(O)R.sub.10 R.sub.11)
Alkyl phosphites are heated with benzylic halides to give phosphonates. The reaction is known as the Arbuzov reaction and it is reviewed by Arbuzov, Pure Appl. Chem., 9 (1964), 307-335.
AMINES (R.sub.2 .dbd.CH(R.sub.17)NR.sub.12 R.sub.13)
Tertiary amines are prepared by alkylation of a secondary amine with a benzylic halide. The reaction is well documented in the literature.
Primary amines can be prepared by reduction of compounds of Formula II where R.sub.2 is azide. Generally lithium aluminum hydride or hydrogen and palladium catalyst are used.
NITRO (R.sub.2 .dbd.CH(R.sub.17)NO.sub.2)
Nitrites react with benzylic halides to give benzylic nitro compounds. The reaction is usually carried out with sodium nitrite on a benzylic bromide in dimethylformamide or dimethylsulfoxide. When silver nitrite is used, diethyl ether at 0.degree.-25.degree. C. are the preferred reaction conditions. The reaction is exhaustively discussed by N. Kornblum, Org. Reactions, 12 (1962), 101.
SELENO ETHERS (R.sub.2 .dbd.CH(R.sub.17)SeR.sub.14)
Alkali alkylselenides can be prepared by in situ combination of an alkali metal t-butoxide with the selenol HSeR.sub.14 in the solvent to be used for the displacement reaction. The selenols, HSeR.sub.14, can be prepared by a variety of methods reviewed by D. L. Klayman, "Selenols and their Derivatives" in Organic Selenium Compounds: Their Chemistry and Biology, D. L. Klayman, W. H. H. Gunther ed., New York, 1973, and K. J. Irgolic and M. V. Kudchadker, "Organic Chemistry of Selenium" in Selenium, R. A. Zingaro, W. C. Cooper ed., Van Nostrand Reinhold, New York, 1974.
Benzyl halides may be formed through a variety of methods described in the literature. Several are listed below.
BENZYLIC CHLORIDES (X.sup.1 .dbd.Cl)
Treatment of alkyl benzene derivatives with N-chlorosuccinimide, NCS, in a suitable solvent, such as carbon tetrachloride or dichloromethane, and catalyzed by light or a free radical initiator, such as azoisobutyronitrile or benzoyl peroxide, gives the benzylic chloride.
Treatment of a benzylic alcohol with thionyl chloride, either neat or in the presence of a base such as pyridine, gives the benzylic chloride. For typical examples, see H. Gilman and J. E. Kirby, J. Am. Chem., Soc., 51, 3475 (1929) and M. S. Newman, J. Am. Chem. Soc., 62, 2295 (1940).
BENZYLIC BROMIDES (X.sup.1 .dbd.Br)
Treatment of alkyl benzene derivatives with N-bromosuccinimide by a method analogous to the case of N-chlorosuccinimide gives the benzylic bromide. Benzylic alcohols in an inert solvent such as benzene or dichloromethane react with phosphorus tribromide to give benzylic bromides.
BENZYLIC IODIDES (X.sup.1 .dbd.I)
Treatment of a benzylic chloride or benzylic bromide with sodium iodide gives the benzylic iodide. The reaction, known as the Finkelstein reaction, works well in refluxing acetone.
Benzylic alcohols may be treated with iodine and phosphorus (red) or phosphorus (red) and phosphorus (yellow) to give the benzylic iodide.
Compounds of Formua II, where R.sub.2 contains an oxygen functionality, such as an aldehyde or ketone, may be prepared by a variety of methods known to one skilled in the art. Two such routes are shown below. ##STR19##
Primary and secondary benzylic halides may be oxidized to aldehydes and ketones, respectively using dimethylsulfoxide. For reviews of this reaction see Durst, Adv. Org. Chem., 285-388 (1969) pp. 343-356 and W. Epstein and F. Sweat, Chem. Rev., 67 (1967), 247-60.
Primary benzylic alochols may be oxidized to aldehydes and secondary benzylic alcohols may be oxidized to ketones by one skilled in the art. One or more of a variety of methods, such as an oxidizing agent, catalytic dehydrogenation, Oppenauer oxidation or halosuccinimide oxidation may be used.
Acetals, thioacetals, ketals and thioketals are easily prepared by one skilled in the art from compounds of Formula V.
Oximes, and oxime ethers of Formula Va are easily prepared by one skilled in the art from compounds of Formula V and hydroxylamine or o-alkyl-hydroxylamine with or without an appropriate base. ##STR20##
Benzylic alcohols and alkyl benzene derivatives are either known or may be prepared by one skilled in the art.
The heterocyclic amines A-1 to A-7 are either known, disclosed in this application or can be prepared by methods obvious to one skilled in the art.
For a review of the synthesis and reactions of 2-aminopyrimidines (A-1, Z.dbd.CH) see The Chemistry of Heterocyclic Compounds, Vol 16, Wiley-Interscience, New York (1962). For a review of the synthesis and reactions of 2-amino-1,3,5-triazines (A-1, Z.dbd.N) see The Chemistry of Heterocyclic Compounds, Vol. 13, Wiley-Interscience, New York (1959), F. C. Schaefer, U.S. Pat. No. 3,154,537 and F. C. Schaefer and K. R. Huffman, J. Org. Chem., 28 (1963), 1812.
The synthesis of bicyclic amines A-2 and A-3 is taught in U.S. Pat. No. 4,339,267.
The synthesis of amino furo [2,3-d]pyrimidines, A-4, is taught in U.S. Pat. No. 4,487,626.
The synthesis of aminotriazoles, A-5, is taught in U.S. Pat. No. 4,421,550.
The synthesis of aminomethylheterocycles, A-6, is taught in U.S. Pat. No. 4,496,392.
The synthesis of aminocyano heterocycles, A-7, is taught in European Publication No. 125,864 (published 11/21/84).
Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by contacting copounds of Formula I with a solution of an alkali or alkaline earth metal salt having a sufficiently basic anion (e.g. hydroxide, alkoxide, carbonate or hydride). Quaternary amine salts can be made by similar techniques.
Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct contacting of an aqueous solution of a salt of a compound of Formula I (e.g., alkali metal or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water, e.g., a copper salt, and can be separated by filtration.
Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged. In this method, the cation of the resin is exchanged for that of the original salt of the resin is exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g., a potassium, sodium or calcium salt.
Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.





The preparation of the compounds of this invention is further illustrated by the following examples.
EXAMPLE 1
5-Bromomethyl-N-(1,1-dimethylethyl)-2-methoxybenzenesulfonamide
A mixture of 27 g of N-(1,1-dimethylethyl)-2-methoxy-5-methylbenzenesulfonamide (E. H. Huntress and F. H. Carten, J. Am. Chem. Soc., 62 (1940), 603), 19.6 g NBS and 0.3 g azobisisobutyronitrile in 200 ml CH.sub.2 Cl.sub.2 was refluxed and illuminated with a sun lamp. After 8 hours the lamp was turned off and the reaction was refluxed for another 24 hr. The reaction was allowed to cool. The reaction mixture was washed with 200 ml of a 1:1:1:1 mixture of brine:sodium sulfite-sodium bicarbonate-water. The organic layer was dried (MgSO.sub.4), treated with charcoal and filtered through a 5 g plug of silica gel. The plug was washed with 100 ml of chloroform. The combined organic fractions were evaporated to give 34 g of solid, m.p. 137.degree.-142.degree. C.;
NMR (CDCl.sub.3, 200 MHz).delta.: 1.15 (s, CH.sub.3, 9H), 4.0 (s, OCH.sub.3, 3H), 4.45 (s, CH.sub.2, 2H), 4.95 (bs, NH, 1H), 7.0-8.6 (m, ArH, 3H).
EXAMPLE 2
5-Cyanomethyl-N-(1,1-dimethylethyl)-2-methoxybenzenesulfonamide
A mixture of 1.63 g potassium cyanide and 8 g of the compound from Example 1 in 50 ml of DMSO was stirred at room temperature overnight. The solution became darker in color with time, going from orange to purple to black. After being stirred overnight the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO.sub.4), filtered and the solvent evaporated. The residual red oil was eluted through a dry silica column with 20% ethyl acetate-80% dichloromethane. The product band was isolated to give 3.0 g solid m.p. 146.degree.-147.degree. C.;
NMR (CDCl.sub.3, 90 MHz): 1.1 (s, CH.sub.3, 9H), 3.7 (s, CH.sub.2 CN, 2H), 4.0 (s, OCH.sub.3, 3H), 5.0 (s, NH, 1H), 6.9-8.0 (m, ArH, 3H).
EXAMPLE 3
5-Cyanomethyl-2-methoxybenzenesulfonamide
A suspension of 3.0 g of the compound from Example 2 and 0.1 g p-toluenesulfonic acid in 100 ml of dry toluene was refluxed in a flask equipped with a Dean-Stark apparatus. After being refluxed overnight the solution was concentrated and allowed to cool. The precipitate was filtered off to give 0.5 g light brown solid. The mother liquor was chromatographed over silica gel with 20:73:2:5, ethyl acetate:methylene chloride:methanol:THF to give additional product, m.p. 173.degree.-177.degree. C.;
NMR (DMSO-d.sub.6, 90 MHz).delta.: 3.9 (s, OCH.sub.3, 3H), 4.0 (s, CH.sub.2 CN, 2H), 7.1 (bs, NH.sub.2, 2H), 7.2-7.8 (m, ArH, 3H).
EXAMPLE 4
5-(Cyanomethyl)-N-((4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl)-2-methoxybenzenesulfonamide
To a suspension of 0.3 g of the compound from Example 3 and 0.37 g 4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 15 ml of dry acetonitrile was added 0.198 ml DBU. After being stirred overnight the clear solution was diluted with 50 ml of water, acidified with 1N HCl and the precipitate was filtered off. The residue was washed with water and triturated with ether to give 0.44 g solid, m.p. 168.degree.-171.degree. C. (dec.);
IR (nujol) 1711 cm.sup.-1 ;
NMR (200 MHz, DMSO-d.sub.6).delta.: 3.76 (s, OCH.sub.3, 3H), 3.91 (s, OCH.sub.3, 6H), 4.10 (s, CH.sub.2, 2H) 6.02 (s, Het-H, 1H), 7.2-7.9 (m, ArH, 3H), 10.5+12.8 (S, NH, 2X1H).
EXAMPLE 5
5-(Bromomethyl)-2-carboxymethylbenzenesulfonamide
A solution of 3.5 g (0.0153 mole) of 5-methyl-2-carboxymethylbenzenesulfonamide, 2.86 g N-bromosuccinimide, 0.05 g azobisisobutyronitrile in 50 ml of carbon tetrachloride and 50 ml dichloromethane was prepared under a nitrogen atmosphere. The solution was refluxed and irradiated with a sun lamp for 4 h. Then 0.6 g N-bromosuccinimide was added. After three hours of further irradiation the reaction was cooled and filtered to give 4.7 g of a white solid. The solid was washed with 200 ml of dichloromethane to leave 1.0 g of product. The mother liquor was eluted through a dry silica gel column with 5% diethyl ether/95% dichloromethane to give an additional 2.3 g of product, m.p. 171.degree.-173.degree. C.;
NMR (CDCl.sub.3, 200 MHz).delta.: 4.0 (s, OCH.sub.3, 3H), 4.52 (s, CH.sub.2 Br, 2H) 5.76 (s, NH.sub.2, 2H), 7.6-8.2 (m, ArH, 3H).
EXAMPLE 6
5-(Cyanomethyl)-2-carboxymethylbenzenesulfonamide
To a solution of 0.31 g potassium cyanide in 20 ml of dry dimethylsulfoxide was added 1.4 g (4.55 mmol) of the compound from Example 5. After being stirred for 6 h, the reaction mixture was partitioned between ethyl acetate amd water. The water layer was neutralized to pH 7, the layers separated and the organic layer was dried (MgSO.sub.4). This solution was placed on a dry silica gel column and eluted with 40% ethyl acetate/60% hexane followed by 60% ethyl acetate/40% hexane. The product band (R.sub.f 0.5, 60% ethyl acetate/40% hexane) was extracted with ethyl acetate, concentrated and the residue triturated with diethyl ether to give 0.26 g of a solid, m.p. 125.degree.-129.degree. C.;
MS (m/e) 254 (M.sup.+);
IR (Nujol) 1711 cm.sup.-1 ;
NMR (200 Mhz, DMSO-d.sub.6).delta.: 3.82 (s, OCH.sub.3), 4.24 (s, CH.sub.2 CN), 7.36 (s, NH.sub.2), 7.65 (dd, ArH, 2H), 7.95 (s, ArH, 1H).
EXAMPLE 7
4-(Cyanomeethyl)-2-[((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)aminosulfonyl]benzoic acid, methyl ester
To a suspension of 0.12 g of the compound from Example 6 and 0.143 g of 4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 15 ml of dry acetonitrile was added 72.7 .mu.of 1.8-diazabicyclo[5.4.0]undec-7-ene (DBU). After being stirred at room temperature for one hour, the reaction mixture was diluted with 50 ml of water, acidified with 1N hydrochloric acid to pH 2 and extracted with ethyl acetate. The organic solution was dried (MgSO.sub.4), filtered and concentrated to an oil. Trituration of the residue with 3:1 (ethyl ether:acetonitrile) gave 0.16 g of a white solid, m.p. 177.degree.-179.degree. C.;
IR (nujol) 1725 cm.sup.-1 ;
NMR (DMSO-d.sub.6, 200 MHz).delta.: 3.78 (s, OCH.sub.3, 3H), 3.92 (s, OCH.sub.3, 6H), 4.31 (s, CH.sub.2, 2H), 6.01 (S, Het-H, 1H), 7.7-8.2 (m, ArH, 3H), 10.6 and 12.7 (two s, NH, 2X1H).
EXAMPLE 8
5-Acetyl-2-ethoxybenzenesulfonamide
To a solution of 30.6 g of 4-ethoxyacetophenone in 100 ml of chloroform was added 40 ml of chlorosulfonic acid dropwise. The reaction was then refluxed for five hours after which it was poured into 800 ml of ice water. The reaction mixture was extracted with 400 ml of chloroform. The organic layer was washed with brine, dried (MgSO.sub.4) and filtered through charcoal. The filtrate was concentrated under reduced essure to give 12.3 g of an oil. The oil was dissolved in 200 ml tetrahydrofuran. The solution was cooled to 5.degree. C. followed by dropwise addition of 10 ml of concentrated ammonium hydroxide. After stirring overnight at room temperature, the reaction was partitioned between water and ethyl acetate. The organic layer was washed with 1N hydrochloric acid, brine, dried (MgSO.sub.4), filtered and stripped. The residue was crystallized from acetonitrile/diethyl ether. The solid was washed with methanol and dried to give 2.3 g of solid, m.p. 148.degree.-151.degree. C.;
NMR (90 MHz, CDCl.sub.3).delta.: 1.5 (m, CH.sub.3, 3H), 2.55 (s, CH.sub.3, 3H), 4.35 (q, CH.sub.2 O, 2H), 5.1 (bs, NH.sub.2), 7.0-8.6 (m, ArH, 3H).
EXAMPLE 9
5-Acetyl-N-((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-2-ethoxybenzenesulfonamide
To a stirred suspension of 0.2 g of the compound from Example 8, 0.23 g of 4,6-dimethoxy-2-pyrimidinylcarbamic acid, phenyl ester in 10 ml of dry acetonitrile was added 127 .mu.l of DBU. After being stirred for 1 hr. the mixture was treated with 40 ml of water and 1N HCl in a dropwise manner until the pH was 3. The precipitate was filtered off and washed with water and ether/hexane (1/1), to give 0.27 g of a solid, m.p. 192.degree.-193.degree. C.;
IR (nujol) 1680 and 1705 cm.sup.-1 ;
NMR (200 MHz, DMSO-d.sub.6).delta.: 1.1 (t, CH.sub.3, 3H), 2.58 (s, CH.sub.3, 3H) 3.91 (s, OCH.sub.3, 6H), 4.27 (q, CH.sub.2, 2H), 6.03 (s, Het-H, 1H), 7.2-8.4 (m, ArH, 3H), 10.6 and 12.7 (s, NH, 2.times.1H).
The invention is further exemplified, but not limited to the compounds in Tables I-VII. The compounds depicted in these tables may be prepared by methods described in Examples 1-9, or by modifications thereof apparent to those skilled in the art. ##STR21##
TABLE I__________________________________________________________________________General Formula I m.p.R.sub.1 R.sub.2 W R X Y Z (.degree.C.)__________________________________________________________________________F CH.sub.2 CN O H OCH.sub.3 H CHF CH.sub.2 CN O CH.sub.3 OCH.sub.3 CH.sub.3 CHF CH.sub.2 CN O H CH.sub.3 OCH.sub.3 NF CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 CHF CH.sub.2 SCN O H OCH.sub.3 CH.sub.2 CH.sub.3 CHF CH.sub.2 SCN O H CH.sub.2 CH.sub.3 OCH.sub.3 NF CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 CH.sub.2 OCH.sub.3 CHF CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHF CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.2 CH.sub.3 CH.sub.3 CHF CH.sub.2 P(O)(CH.sub.3).sub.2 O H OCH.sub.3 CH.sub.3 NCl CH.sub.2 CN O H OCH.sub.3 CH.sub.2 CH.sub.2 OCH(CH.sub.3) .sub.2 CHCl CH.sub.2 CN O H Cl OCH.sub. 3 CHCl CH.sub.2 CN O H OCH.sub.3 CH(CH.sub.3)(CH.sub.2 OCH.sub.3 ) CHCl CH.sub.2 SCN O H CH CH.sub.3 CH.sub.3 143-153Cl CH.sub.2 SCN O H OCH.sub.3 CH.sub.3 N 100-106Cl CH.sub.2 SCN O H OCH.sub.3 CH.sub.3 CH 174-180Cl CH.sub.2 SCN O H Cl OCH.sub.3 CH oilCl CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 N oilCl CH.sub.2 SCN O H OCH.sub.3 (CH.sub.2).sub.4 CH.sub.2 OCH.sub.2 CH.sub.3 CHCl CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 CH.sub.3 NCl CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCF.sub.2 H CH.sub.3 CHCl CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 NH.sub.2 CHCl CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2 O H OCH.sub.3 NHCH.sub.3 NBr CH.sub.2 CN O H CH.sub.3 NHCH.sub.2 CH.sub.3 CHBr CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHBr CH.sub.2 CN S H OCH.sub.3 CH.sub.3 NBr CH.sub.2 SCN O H CH.sub. 2 F OCH.sub.3 CHBr CH.sub.2 SCN O H OCH.sub.3 NHCH(CH.sub.3).sub.2 CHBr CH.sub.2 SCN O H OCH.sub.3 CH.sub.3 NBr CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.2 CH.sub.2 F OCH.sub.3 CHBr CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 N(CH.sub.3).sub.2 CHBr CH.sub.2 P(O)(SCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 NNO.sub.2 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHNO.sub.2 CH.sub.2 CN O H OCH.sub.3 CH.sub.3 CHNO.sub.2 CH.sub.2 CN O H CH.sub.3 OCH.sub.3 CHNO.sub.2 CH.sub.2 SCN O H OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 NNO.sub.2 CH.sub.2 SCN O H CH.sub.2 CH.sub.3 OCH.sub.3 CHNO.sub.2 CH.sub.2 SCN O H OCH.sub.3 OCH.sub.2 CH.sub.2 CH.sub.2 CHNO.sub.2 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 NNO.sub.2 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 CHNO.sub.2 CH.sub. 2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 SCH.sub.2 CH.sub.2 F CHNO.sub.2 CH.sub.2 P(S)(SCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 NCH.sub.3 CH.sub.2 CN O H CH.sub.3 SCH.sub.3 CHCH.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHCH.sub.3 CH.sub.2 SCN O H OCH.sub.3 SCH(CH.sub.3).sub.2 NCH.sub.3 CH.sub.2 SCN O H OCH.sub.2 CH(CH.sub.3).sub.2 OCH.sub.3 CHCH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H Br OCH.sub.3 CHCH.sub.3 CH.sub.2 P(O)(N(CH.sub.3).sub.2).sub.2 O H OCH.sub.3 OCH.sub.3 NCH.sub.2 CH.sub.3 CH.sub.2 CN O H CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3 CHCH.sub.2 CH.sub.3 CH.sub.2 SCN O H OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3 CH -n-C.sub.4 H.sub.9 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 NCHCH.sub.2 CH.sub.2 CN O H F OCH.sub.3 CHCHCHCH.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 CHCH.sub.2 CH.sub.2 SCN O H CH.sub.3 OCH.sub.3 NCClCCl.sub.2 CH.sub.2 SCN O H OCH.sub.2 CH.sub.2 OCH(CH.sub.3).sub.2 OCH.sub.3 CHCCCH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H CH.sub.3 OCH.sub.3 CHCH.sub.2 CCH CH.sub.2 CN O H OCH.sub.3 CH.sub.2 CH.sub.3 NCH.sub.2 Cl CH.sub.2 CN O H N(CH.sub.2 CH.sub.3).sub.2 OCH.sub.3 CHCH.sub.2 Cl CH.sub.2 SCN O H Cl OCH.sub.3 CHCH.sub.2 Br CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 NCH.sub.2 Br CH.sub.2 CN O H CH.sub.3 OCH.sub.3 CHCF.sub.3 CH.sub.2 CN O H OCH.sub.3 CH.sub.3 NCF.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHCF.sub.3 CH.sub.2 SCN O H Br OCH.sub.3 CHCF.sub.3 CH.sub.2 SCN O H OCH.sub.3 CH.sub.2 CH.sub.2 NCF.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHCF.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.2 CH.sub.3 CH.sub.3 CHCF.sub.3 CH.sub.2 NH.sub.2 O H OCH.sub.3 H CHCH.sub.2 CHClCH.sub.2 Cl CH.sub.2 CN O H CH.sub.3 OCH.sub.3 NCH.sub.2 CF.sub.3 CH.sub.2 CN O H I OCH.sub.3 CHOCH.sub.3 CH.sub.2 CN O H OCH.sub.3 CH.sub.2 OCH.sub.3 CHOCH.sub.3 CH.sub.2 CN O H CH.sub.3 OCH.sub.3 CHOCH.sub.3 CH.sub.2 CN O H CH.sub.3 OCH.sub.3 N 166-170.degree.OCH.sub.3 CH.sub.2 CN O H OCH.sub.3 NHCH.sub.3 CHOCH.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NOCH.sub.3 CH.sub.2 CN O H OCH.sub.2 CF.sub.2 H OCH.sub.3 CHOCH.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CH 168-171.degree.OCH.sub.3 CH.sub.2 CN O H CH.sub.3 CH.sub.3 NOCH.sub.3 CH.sub.2 SCN O H CH.sub.2 Br OCH.sub.3 CHOCH.sub.3 CH.sub.2 SCN O H CH.sub.3 OCH.sub.3 CHOCH.sub.3 CH.sub.2 SCN O H OCH.sub.3 N(CH.sub.3).sub.2 NOCH.sub.3 CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 CHOCH.sub.3 CH.sub.2 SCN O H CH.sub.3 OCH.sub.3 CHOCH.sub.3 CH.sub.2 SCN O H OCH.sub.3 SCH.sub.3 NOCH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.2 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CH.sub.2 SCN O H OCH.sub.3 CH.sub.3 CHOSO.sub.2 CH.sub.3 CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 CHOSO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H CH.sub.3 OCH.sub.3 NOSO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 COCH.sub.3 CHOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H CH.sub.3 OCH.sub.3 CHOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 CH(OCH.sub.3).sub.2 CHOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 CH.sub.3 NOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 SCN O H CH.sub.3 OCH.sub.3 CHOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 CHOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 SCN O H OCH.sub.3 CH.sub.3 CHOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H CH.sub.3 OCH.sub.3 CHOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 CH.sub.3 NOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H CH.sub.2 CH.sub.3 OCH.sub.3 CHOSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 CH(SCH.sub.3)(OCH.sub.2 CH.sub.3) CHOSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NOSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHOSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 CH.sub.3 CHCH.sub.2 OCH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 NCH.sub.2 SCH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H CH.sub.3 C(CH.sub.3)(SCH.sub.3).sub.2 CHCH.sub.2 CH.sub.3 OCH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NCH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 1,3-dioxolan-2-yl CHCH.sub.2 CN CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NC.sub.2 H.sub.5 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHC.sub.2 H.sub.5 CH.sub.2 CN O H OCH.sub.3 CH.sub.3 CHC.sub.2 H.sub.5 CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 NC.sub.2 H.sub.5 CH.sub.2 SCN O H OCH.sub.3 2-methyl-1,3- CH oxathion-2-ylCOCH.sub.3 CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 CHCOCH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H CH.sub.3 OCH.sub.3 NCOCCCH.sub.3 CH.sub.2 CN O H OCH.sub.3 CH.sub.3 CHCOCH.sub.2 CH.sub.2 Cl CH.sub.2 CN O H CH.sub.3 OCH.sub.3 CHC(O)--cyclo- CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NpropylC(O)--cyclo- CH.sub.2 CN O H CH.sub.3 OCH.sub.3 CHpropylC(O)--cyclo- CH.sub.2 SCN O H OCH.sub.3 CH.sub.3 CHpropylCH(OCH.sub.3).sub.2 CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 NCH(OCH.sub.3).sub.2 CH.sub.2 SCN O H CH.sub.3 OCH.sub.3 CHCH(OCH.sub.2 CH.sub.3).sub.2 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHCH(OCH.sub.2 CH.sub.3).sub.2 CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 CH.sub.3 CH1,3-dioxyl-2-yl CH.sub.2 CN O H CH.sub.3 OCH.sub.3 CH1,3-dioxyl-2-yl CH.sub.2 CN O H OCH.sub.3 CH.sub.3 NR.sub.1A CH.sub.2 CN O H CH.sub.2 CH.sub.3 OCH.sub.3 CHR.sub.1A CH.sub.2 CN O H OCH.sub.3 1,3-oxathion-2-yl CHR.sub.1A CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NR.sub.1A CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHR.sub.1A CH.sub.2 CN O H OCH.sub.3 CH.sub.3 CHR.sub.1A CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 NR.sub.1A CH.sub.2 SCN O H CH.sub.3 2-methyl-1,3- CH dithian-2-ylR.sub.1A CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHR.sub.1A CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 NR.sub.1A CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHR.sub.1B CH.sub.2 CN O H OCH.sub.3 CH.sub.3 CHR.sub.1B CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NR.sub.1B CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHR.sub.1B CH.sub.2 CN O H OCH.sub.3 4-methyl-1,3- CH dioxolan-2-ylR.sub.1B CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 NR.sub.1B CH.sub.2 SCN O H Cl OCH.sub.3 CHR.sub.1B CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 CHR.sub.1B CH.sub.2 SCN O H CH.sub.3 OCH.sub.3 NR.sub.1B CH.sub.2 P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHR.sub.1B CH.sub.2 P(O)(OCH.sub.3).sub.2 O H CH.sub.3 OCH.sub.3 CHR.sub.1C CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NR.sub.1C CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHR.sub.1C CH.sub.2 CN O H OCH.sub.3 4-methyl-1,3- CH oxathiolan-2-ylR.sub.1C CH.sub.2 CN O H OCH.sub.3 CH.sub.3 NR.sub.1C CH.sub.2 SCN O H CH.sub.3 OCH.sub.3 CHR.sub.1C CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 CHR.sub.1C CH.sub.2 SCN O H OCH.sub.3 CH.sub.3 CHR.sub.1C CH.sub.2 P(O)(OMe).sub.2 O H CH.sub.3 OCH.sub.3 CHR.sub.1C CH.sub.2 P(O)(OMe).sub.2 O H OCH.sub.3 OCH.sub.3 NR.sub.1C CH.sub.2 P(O)(OMe).sub.2 O H CH.sub.2 CH.sub.3 OCH.sub.3 CHR.sub.1D CH.sub.2 P(O)(OMe).sub.2 O H OCH.sub.3 2,4-dimethyl-1,3- CH dithiolan-2-ylR.sub.1D CH.sub.2 P(O)(OMe).sub.2 O H OCH.sub.3 OCH.sub.3 NR.sub.1E CH.sub.2 P(O)(OMe).sub.2 O H OCH.sub.3 OCH.sub.3 CHR.sub.1F CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHR.sub.1G CH.sub.2 CN O H OCH.sub.3 N(OCH.sub.3)CH.sub.3 CHR.sub.1H CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NR.sub.1I CH.sub.2 CN O H CH.sub.3 CH.sub.3 CHR.sub.1J CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 CHR.sub.1K CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 NR.sub.1L CH.sub.2 SCN O H OCH.sub.3 OCH.sub.3 CHR.sub.1M CH.sub.2 SCN O H OCH.sub.3 CH.sub.3 CHR.sub.1N CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NR.sub.1O CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHR.sub.1P CH.sub.2 CN O H Cl OCH.sub.3 CHR.sub.1Q CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NR.sub.1R CH.sub.2 P(O)(OMe).sub.2 O H OCH.sub.3 OCH.sub.3 CHR.sub.1S CH.sub.2 P(O)(OMe).sub.2 O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 O H OCH.sub.3 CH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 O H CH.sub.3 CH.sub.3 CH 165-170CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 O H Cl OCH.sub.3 CH 146-148CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 O H OCH.sub.3 OCH.sub.3 NCO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H Cl OCH.sub.3 CH 104-115CO.sub.2 CH(CH.sub.3).sub.2 CH.sub.2 N.sub.3 O H OCH.sub.3 OCH.sub.3 CH 149-150CO.sub.2 CH(CH.sub.3).sub.2 CH.sub.2 N.sub.3 O H OCH.sub.3 CH.sub.3 CH 142-144CO.sub.2 CH(CH.sub.3).sub.2 CH.sub.2 N.sub.3 O H Cl OCH.sub.3 CH 161-162CO.sub.2 CH(CH.sub.3).sub.2 CH.sub.2 N.sub.3 O H CH.sub.3 CH.sub.3 CH 171-173CO.sub.2 CH(CH.sub.3).sub.2 CH.sub.2 N.sub.3 O H OCH.sub.3 OCH.sub.3 N 133-134CO.sub.2 CH(CH.sub.3).sub.2 CH.sub.2 N.sub.3 O H OCH.sub.3 CH.sub.3 N 125-127CO.sub.2 CH(CH.sub.3).sub.2 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CH 138-140CO.sub.2 CH(CH.sub.3).sub.2 CH.sub.2 CN O H Cl OCH.sub.3 CHCO.sub.2 CH(CH.sub.3).sub.2 CH.sub.2 CN O H OCH.sub.3 CH.sub.3 CHCO.sub.2 CH(CH.sub.3).sub.2 CH.sub.2 CN O H CH.sub.3 CH.sub.3 CH 167-169CO.sub.2 CH(CH.sub.3).sub.2 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 NCO.sub.2 CH(CH.sub.3).sub.2 CH.sub.2 CN O H OCH.sub.3 CH.sub.3 NCl CH(CH.sub.3)CN O H OCH.sub.3 OCH.sub.3 CHOCH.sub.3 CHFCN O H OCH.sub.3 CH.sub.3 CHCO.sub.2 CH.sub.3 CH(CH.sub.2 CH.sub.3)SCN O H CH.sub.3 CH.sub.3 CHNO.sub.2 CH(CH.sub.3)P(O)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHSO.sub.2 N(CH.sub. 3).sub.2 CH(CH.sub.2 CH.sub.3)P(S)(CH.sub.3).sub.2 O H OCH.sub.3 CH.sub.3 NCO.sub.2 N(CH.sub.3).sub.2 CH(CH.sub.3)N(CH.sub.3).sub.2 O H Cl OCH.sub.3 CHOCH.sub.3 CH(OC(O)CH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 NOCH.sub.3 CH(CH.sub.2 CH.sub.3)N.sub.3 O H OCH.sub.3 CH.sub.3 CHCl CH(CH.sub.3)SeCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.3 CH(CH.sub.2 CH.sub.3)N.sub.3 O H OCH.sub.3 OCH.sub.3 CHOCH.sub.2 CH.sub.3 CH(CH.sub.3)N.sub.3 O H OCH.sub.3 OCH.sub.3 CHOCH.sub.2 CH.sub.3 CH(CH.sub.3)N.sub.3 O H OCH.sub.3 CH.sub.3 CHOCH.sub.2 CH.sub.3 CH(CH.sub.3)N.sub.3 O H Cl OCH.sub.3 CHOCH.sub.2 CH.sub.3 CH(CH.sub.3)N.sub.3 O H OCH.sub.3 OCH.sub.3 NOCH.sub.2 CH.sub.3 CH(CH.sub.3)N.sub.3 O H OCH.sub.3 CH.sub.3 NOCH.sub.2 CH.sub.3 CH(CH.sub.3)CN O H OCH.sub.3 OCH.sub.3 CHOCH.sub.2 CH.sub.3 CH(CH.sub.3)CN O H OCH.sub.3 CH.sub.3 CHOCH.sub.2 CH.sub. 3 CH(CH.sub.3)CN O H OCH.sub.3 CH.sub.3 NCO.sub.2 CH.sub.3 CH(CH.sub.2 CH.sub.3)NC O H OCH.sub.3 OCH.sub.3 CHCl CH(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHNO.sub.2 CH(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 CH(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 CH(OCH.sub.3).sub.2 O H Cl OCH.sub.3 CHOCH.sub.3 CH(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 NOCH.sub.3 CH(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHOCH.sub.2 CH.sub.3 CH(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 NCO.sub.2 CH.sub.3 CH(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 CH(OCH.sub.3).sub.2 O H OCH.sub.3 CH.sub.3 CHCO.sub.2 CH.sub.3 CH(OCH.sub.3).sub.2 O H OCH.sub.3 CH.sub.3 NCO.sub.2 CH.sub.3 CH(OCH.sub.2 CH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2 O H OCH.sub.3 CH.sub.3 CHCO.sub.2 CH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 NCO.sub.2 CH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2 O H CH.sub.3 CH.sub.3 CHCO.sub.2 CH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2 O H Cl OCH.sub.3 CHOCH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHOCH.sub.2 CH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 CHOCH.sub.2 CH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2 O H OCH.sub.3 CH.sub.3 CHOCH.sub.2 CH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2 O H OCH.sub.3 OCH.sub.3 NOCH.sub.2 CH.sub.3 C(CH.sub.3)(OCH.sub.3).sub.2 O H CH.sub.3 CH.sub.3 CHCO.sub.2 CH.sub.3 C(CH.sub.2 CH.sub.3)(OCH.sub.3).sub.2 O H OCH.sub.3 CH.sub.3 CHCO.sub.2 CH.sub.3 CH(SCH.sub.3).sub.3 O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 C(CH.sub.2 CH.sub.3)(SCH.sub.3).sub. 2 O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 O H OCH.sub.3 OCH.sub.3 CHOCH.sub.3 ##STR22## O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 CH(CN)(OSi(CH.sub.3).sub.3) O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 CH(CN)(OSi(CH.sub.3).sub.3) O H OCH.sub.3 CH.sub.3 CHCO.sub.2 CH.sub.3 C(CH.sub.3)(CN)OH O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 C(CH.sub.2 CH.sub.3)(CN)OCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 1,-3-dithiolan-2-yl O H OCH.sub.3 OCH.sub.3 NCO.sub.2 CH.sub.3 1,-3-dithiolan-2-yl O H Cl OCH.sub.3 CHCl 1,-3-dithiolan-2-yl O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 1,-3-dioxolan-2-yl O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 1,-3-dioxolan-2-yl O H OCH.sub.3 CH.sub.3 CHNO.sub.2 1,-3-dioxolan-2-yl O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 2-methyl-1,3- O H OCH.sub.3 OCH.sub.3 CH dioxolan-2-ylCO.sub.2 CH.sub.3 1,-3-dioxolan-2-yl O H OCH.sub. 3 OCH.sub.3 NCO.sub.2 CH.sub.3 1,-3-dioxolan-2-yl O H OCH.sub.3 CH.sub.3 CHCO.sub.2 CH.sub.3 1,-3-dioxolan-2-yl O H Cl OCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 1,-3-dithian-2-yl O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 2-methyl-1,3- O H OCH.sub.3 OCH.sub.3 CH dioxan-2-ylC.sub.6 H.sub.5 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CHCl ##STR23## O H OCH.sub.3 OCH.sub.3 CHNO.sub.2 ##STR24## O H OCH.sub.3 OCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 ##STR25## O H OCH.sub.3 OCH.sub.3 CHOCH.sub.3 ##STR26## O H OCH.sub.3 OCH.sub.3 CHOCH.sub.3 ##STR27## O H OCH.sub.3 CH.sub.3 CHOCH.sub.3 ##STR28## O H OCH.sub.3 OCH.sub.3 CHOCH.sub.2 CH.sub.3 ##STR29## O H OCH.sub.3 OCH.sub.3 CHOCH.sub.2 CH.sub.3 ##STR30## O H OCH.sub.3 OCH.sub.3 CH 192-192OCH.sub.2 CH.sub.3 ##STR31## O H OCH.sub.3 CH.sub.3 N 188-190OCH.sub.2 CH.sub.3 ##STR32## O H CH.sub.3 CH.sub.3 CH 180-181OCH.sub.2 CH.sub.3 ##STR33## O H OCH.sub.3 CH.sub.3 CH 137-138OCH.sub.2 CH.sub.3 ##STR34## O H Cl OCH.sub.3 CHOCH.sub.2 CH.sub.3 ##STR35## O H OCH.sub.3 OCH.sub.3 N 135-136OCH.sub.2 CH.sub.3 ##STR36## O H OCH.sub.3 OCH.sub.3 CHOCH.sub.2 CH.sub.3 ##STR37## O H OCH.sub.3 OCH.sub.3 NOCH.sub.2 CH.sub.3 ##STR38## O H Cl OCH.sub.3 CHCO.sub.2 CH.sub.3 ##STR39## O H OCH.sub.3 OCH.sub.3 CH 189-190CO.sub.2 CH.sub.3 ##STR40## O H OCH.sub.3 CH.sub.3 CH 115CO.sub.2 CH.sub.3 ##STR41## O H Cl OCH.sub.3 CH 182-184CO.sub.2 CH.sub.3 ##STR42## O H OCH.sub.3 OCH.sub.3 N 174-175CO.sub.2 CH.sub.3 ##STR43## O H OCH.sub.3 CH.sub.3 N 150-154CO.sub.2 CH.sub.3 ##STR44## O H CH.sub.3 CH.sub.3 CH 145-147CO.sub.2 CH.sub.3 ##STR45## O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.3 ##STR46## O H OCH.sub.3 CH.sub.3 CHCO.sub.2 CH.sub.3 ##STR47## O H OCH.sub.3 OCH.sub.3 NCO.sub.2 CH.sub.3 ##STR48## O H OCH.sub.3 CH.sub.3 NCO.sub.2 CH.sub.2 CH.sub.3 ##STR49## O H OCH.sub.3 OCH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.3 ##STR50## O H OCH.sub.3 CH.sub.3 CHCO.sub.2 CH.sub.2 CH.sub.3 ##STR51## O H Cl OCH.sub.3 CH 123-124OSO.sub.2 CH.sub.3 ##STR52## O H OCH.sub.3 CH.sub.3 CHSO.sub.2 CH.sub.2 CH.sub.3 ##STR53## O H OCH.sub.3 OCH.sub.2 CH.sub.3 CHC(O)N(CH.sub.2 CH.sub.3).sub.2 Cl O H CH.sub.3 CH.sub.3 CH 180-183Cl CH.sub.2 N.sub.3 O H OCH.sub.3 OCH.sub.3 CH 150-152Cl CH.sub.2 N.sub.3 O H OCH.sub.3 CH.sub.3 CH 138-139Cl CH.sub.2 N.sub.3 O H CH.sub.3 CH.sub.3 CH 167-170Cl CH.sub.2 N.sub.3 O H Cl OCH.sub.3 CH 145-147Cl CH.sub.2 N.sub.3 O H OCH.sub.3 OCH.sub.3 N 134-137Cl CH.sub.2 N.sub.3 O H OCH.sub.3 CH.sub.3 N oilCO.sub.2 CH.sub.2 CH.sub.3 ##STR54## O H OCH.sub.3 OCH.sub.3 CH 144-146CO.sub.2 CH.sub.2 CH.sub.3 ##STR55## O H CH.sub.3 CH.sub.3 CH 144-146CO.sub.2 CH.sub.2 CH.sub.3 ##STR56## O H OCH.sub.3 OCH.sub.3 N 146-148CO.sub.2 CH.sub.2 CH.sub.3 ##STR57## O H OCH.sub.3 CH.sub.3 N 142-145CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 O H OCH.sub.3 OCH.sub.3 CH 128CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 O H OCH.sub.3 CH.sub.3 CH 131-132CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 O H CH.sub.3 CH.sub.3 CH 144-147CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 O H Cl OCH.sub.3 CH 156-158CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 O H OCH.sub.3 OCH.sub.3 N 134-135CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 O H OCH.sub.3 CH.sub.3 N oilCO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 CH 130-131CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 CH.sub.3 CH 144-145CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H CH.sub.3 CH CH.sub.3 150-152CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H Cl OCH.sub.3 CH 178-181CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 OCH.sub.3 N oilCO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN O H OCH.sub.3 CH.sub.3 N oilCO.sub.2 CH.sub.3 CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CH 171-174CO.sub.2 CH.sub.3 CHNOCH.sub.3 O H OCH.sub.3 CH.sub.3 CH 188-190CO.sub.2 CH.sub.3 CHNOCH.sub.3 O H CH.sub.3 CH.sub.3 CH 182-185CO.sub.2 CH.sub.3 CHNOCH.sub.3 O H Cl OCH.sub.3 CH 185-188CO.sub.2 CH.sub.3 CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 N 167-169CO.sub.2 CH.sub.3 CHNOCH.sub.3 O H OCH.sub.3 CH.sub.3 N 136-138OCH.sub.2 CH.sub.3 C(CH.sub.3)NOH O H OCH.sub. 3 OCH.sub.3 CH 170-171OCH.sub.2 CH.sub.3 C(CH.sub.3)NOH O H OCH.sub.3 CH.sub.3 CH 183-185OCH.sub.2 CH.sub.3 C(CH.sub.3)NOH O H CH.sub.3 CH.sub.3 CH 180-182OCH.sub.2 CH.sub.3 C(CH.sub.3)NOH O H Cl OCH.sub.3 CH 115-118OCH.sub.2 CH.sub.3 C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 N 95-100OCH.sub.2 CH.sub.3 C(CH.sub.3)NOH O H OCH.sub.3 CH.sub.3 N 112-116OCH.sub.2 CH.sub.3 C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CH 185-187OCH.sub.2 CH.sub.3 C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 CH.sub.3 CHOCH.sub.2 CH.sub.3 C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 NOCH.sub.2 CH.sub.3 C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 CH.sub.3 NF CHNOH O H OCH.sub.3 OCH.sub.3 CHF CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHF C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 CHF C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub. 3 CHCl CHNOH O H OCH.sub.3 OCH.sub.3 CHCl CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCl C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 CHCl C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHNO.sub.2 CHNOH O H OCH.sub.3 OCH.sub.3 CHNO.sub.2 CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHNO.sub.2 C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 CHNO.sub.2 C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCH.sub.3 CHNOH O H OCH.sub.3 OCH.sub.3 CHCH.sub.3 CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCH.sub.3 C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 CHCH.sub.3 C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHC(O)N(CH.sub.3).sub.2 CHNOH O H OCH.sub.3 OCH.sub.3 CHC(O)N(CH.sub.3).sub.2 CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHC(O)N(CH.sub.3).sub.2 C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 CHC(O)N(CH.sub.3).sub.2 C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 CHNOH O H OCH.sub.3 OCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 CHSO.sub.2 N(CH.sub.3).sub.2 C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHSO.sub.2 CH.sub.3 CHNOH O H OCH.sub.3 OCH.sub.3 CHSO.sub.2 CH.sub.3 CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHSO.sub.2 CH.sub.3 C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 CHSO.sub.2 CH.sub.3 CH(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHOSO.sub.2 CH.sub.3 CHNOH O H OCH.sub.3 OCH.sub.3 CHOSO.sub.2 CH.sub.3 CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHOSO.sub.2 CH.sub.3 C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 CHOSO.sub.2 CH.sub.3 C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 OCH.sub.3 CHNOH O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 OCH.sub.3 CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 OCH.sub.3 C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 OCH.sub.3 C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 SCH.sub.3 CHNOH O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 SCH.sub.3 CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 SCH.sub.3 C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 SCH.sub.3 C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 CN CHNOH O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 CN CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 CN C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 CHCH.sub.2 CN C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCH(OCH.sub.3).sub.2 CHNOH O H OCH.sub.3 OCH.sub.3 CHCH(OCH.sub.3).sub.2 CHNOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHCH(OCH.sub.3).sub.2 C(CH.sub.3)NOH O H OCH.sub.3 OCH.sub.3 CHCH(OCH.sub.3).sub.2 C(CH.sub.3)NOCH.sub.3 O H OCH.sub.3 OCH.sub.3 CHR.sub.1A CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1B CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1C CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1D CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1E CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1F CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1G CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1H CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1I CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1J CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1K CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1L CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1M CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1N CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1O CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1P CH NOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1Q CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1R CHNOH O H OCH.sub.3 OCH.sub.3 CHR.sub.1S CHNOH O H OCH.sub.3 OCH.sub.3 CH__________________________________________________________________________
TABLE II______________________________________General Formula II m.p.R.sub.1 R.sub.2 X.sub.1 Y.sub.1 (.degree.C.)______________________________________F CH.sub.2 CN CH.sub.3 OCl.sub.3 CH.sub.2 SCN OCH.sub.3 OCF.sub.3 CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2 OCH.sub.3 CH.sub.2NO.sub.2 CH.sub.2 CN OCH.sub.3 OOCH.sub.3 CH.sub.2 CN OCH.sub.3 OOCH.sub.3 CH.sub.2 SCN OCH.sub.3 CH.sub.2OCH.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3 OOCH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.2CO.sub.2 CH.sub.3 CH.sub.2 CN OCF.sub.2 H OCO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.2CO.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3 OCO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 OCO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 OCO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.3CO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 CN CH.sub.3 OSO.sub.2 NHCH.sub.3 CH.sub. 2 CN OCH.sub.3 OSO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 CN OCH.sub.3 CH.sub.2SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 SCN OCH.sub.3 OSO.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3 OSO.sub.2 CH.sub.3 CH.sub.2 CN OCF.sub.2 H CH.sub.2SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 OSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 OOSO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 CH.sub.2OSO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.2 C OOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3 OR.sub.1 --A CH.sub.2 CN CH.sub.3 OR.sub.1 --A CH.sub.2 SCN OCH.sub.3 CH.sub.2R.sub.1 --B CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 OR.sub.1 --C CH.sub.2 CN OCH.sub.3 OF CH.dbd.NOH CH.sub.3 OOCH.sub.3 CH.dbd.NOH.sub.3 OCH.sub.3 OCOOCH.sub.3 C(CH.sub.3).dbd.NOH OCF.sub.2 H CH.sub.2CO.sub.2 N(CH.sub.3).sub.2 C(CH.sub.3).dbd.NOCH.sub.3 CH.sub.3 OSO.sub. 2 N(CH.sub.3).sub.2 CH.dbd.NOH OCH.sub.3 OSO.sub.2 CH.sub.3 CH.dbd.NOCH.sub.3 OCH.sub.3 CH.sub.2OSO.sub.2 CH.sub.2 CH.sub.3 C(CH.sub.3).dbd.NOH OCF.sub.2 H OR.sub.1 --A C(CH.sub.3).dbd.NOCH.sub.3 CH.sub.3 OR.sub.1 --B CH.dbd.NOH CH.sub.3 CH.sub.2R.sub.1 --C CH.dbd.NOCH.sub.3 OCH.sub.3 O______________________________________
TABLE III______________________________________General Formula IIIR.sub.1 R.sub.2 X.sub.1 m.p. (.degree.C.)______________________________________F CH.sub.2 CN CH.sub.3Cl CH.sub.2 SCN OCH.sub.3CF.sub.3 CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2 OCH.sub.3NO.sub.2 CH.sub.2 CN OCH.sub.3OCH.sub.3 CH.sub.2 CN OCH.sub.3OCH.sub.3 CH.sub.2 SCN OCH.sub.3OCH.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3OCH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CN OCF.sub.2 HCO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3CO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 CN CH.sub.3SO.sub.2 NHCH.sub.3 CH.sub.2 CN OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 CN OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 SCN OCH.sub.3SO.sub.2 CH.sub. 3 CH.sub.2 SCN OCH.sub.3SO.sub.2 CH.sub.3 CH.sub.2 CN OCF.sub.2 HSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3OSO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3OSO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.2 CH.sub.3OSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3R.sub.1 --A CH.sub.2 CN CH.sub.3R.sub.1 --A CH.sub.2 SCN OCH.sub.3R.sub.1 --B CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3R.sub.1 --C CH.sub.2 CN OCH.sub.3F CH.dbd.NOH CH.sub.3OCH.sub.3 CH.dbd.NOCH.sub.3 OCH.sub.3COOCH.sub.3 C(CH.sub.3).dbd.NOH OCH.sub.3CO.sub.2 N(CH.sub.3).sub.2 C(CH.sub.3).dbd.NOCH.sub.3 OCF.sub.2 HSO.sub.2 N(CH.sub.3).sub.2 CH.dbd.NOH CH.sub.3SO.sub.2 CH.sub.3 CH.dbd.NOCH.sub.3 OCH.sub.3OSO.sub.2 CH.sub.2 CH.sub.3 C(CH.sub.3).dbd.NOH CH.sub.3R.sub.1 --A C(CH.sub.3).dbd.NOCH.sub.3 OCH.sub.3R.sub.1 --B CH.dbd.NOH OCF.sub.2 HR.sub. 1 --C CH.dbd.NOCH.sub.3 OCH.sub.3______________________________________
TABLE IV______________________________________General Formula IV m.p.R.sub.1 R.sub.2 X.sub.1 Y.sub.3 (.degree.C.)______________________________________F CH.sub.2 CN CH.sub.3 HCl CH.sub.2 SCN OCH.sub.3 HCF.sub.3 CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2 OCH.sub.3 CH.sub.3NO.sub.2 CH.sub.2 CN OCH.sub.3 HOCH.sub.3 CH.sub.2 CN OCH.sub.3 HOCH.sub.3 CH.sub.2 SCN OCH.sub.3 CH.sub.3OCH.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3 HOCH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CN OCF.sub.2 H HCO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3 HCO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 HCO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 HCO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.3CO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 CN CH.sub.3 HSO.sub.2 NHCH.sub.3 CH.sub.2 CN OCH.sub.3 HSO N(CH.sub.3).sub.2 CH.sub.2 CN OCH.sub.3 HSO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 SCN OCH.sub.3 HSO.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3 HSO.sub.2 CH.sub.3 CH.sub.2 CN OCF.sub.2 H CH.sub.3SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 HSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 HOSO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 CH.sub.3OSO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.2 CH.sub.3 HOSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3 HR.sub.1 --A CH.sub.2 CN CH.sub.3 HR.sub.1 --A CH.sub.2 SCN OCH.sub.3 CH.sub.3R.sub.1 --B CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 HR.sub.1 --C CH.sub.2 CN OCH.sub.3 HF CH.dbd.NOH CH.sub.3 HOCH.sub.3 CH.dbd.NOH.sub.3 CH.sub.3 CH.sub.3COOCH.sub.3 C(CH.sub.3).dbd.NOH OCH.sub.3 HCO.sub.2 N(CH.sub.3).sub.2 C(CH.sub.3).dbd.NOCH.sub.3 OCH.sub.3 HSO.sub.2 N(CH.sub.3 ).sub.2 CH.dbd.NOH CH.sub.3 HSO.sub.2 CH.sub.3 CH.dbd.NOCH.sub.3 CH.sub.3 CH.sub.3OSO.sub.2 CH.sub.2 CH.sub.3 C(CH.sub.3).dbd.NOH CH.sub.3 HR.sub.1 --A C(CH.sub.3).dbd.NOCH.sub.3 OCH.sub.3 HR.sub.1 --B CH.dbd.NOH CH.sub.3 CH.sub.3R.sub.1 --C CH.dbd.NOCH.sub.3 OCH.sub.3 H______________________________________
TABLE V__________________________________________________________________________General Formula VR.sub.1 R.sub.2 X.sub.2 Y.sub.2 m.p. (.degree.C.)__________________________________________________________________________F CH.sub.2 CN CH.sub.3 OCH.sub.3Cl CH.sub.2 SCN CH.sub.3 OCH.sub.2 CH.sub.3CF.sub.3 CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2 CH.sub.3 OCH.sub.3NO.sub.2 CH.sub.2 CN CH.sub.3 SCH.sub.3OCH.sub.3 CH.sub.2 CN CH.sub.2 CH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 SCN CH.sub.3 SCH.sub.2 CH.sub.3OCH.sub.2 CH.sub.3 CH.sub.2 SCN CH.sub.3 OCH.sub.3OCH.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.2 CF.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCN CH.sub.3 CH.sub.2 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 CH.sub.2 CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.3 OCH.sub.2 CH.sub.3CO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 CN CH.sub.2 CF.sub.3 OCH.sub.3SO.sub.2 NHCH.sub.3 CH.sub.2 CN CH.sub.3 OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 CN CH.sub.3 SCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 SCN CH.sub.2 CH.sub.3 OCH.sub.3SO.sub.2 CH.sub.3 CH.sub.2 SCN CH.sub.3 OCH.sub.3SO.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.3 SCH.sub.2 CH.sub.3SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.3 OCH.sub.3SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 CH.sub.2 CF.sub.3 OCH.sub.3OSO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 CH.sub.3 CH.sub.3OSO.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.3 OCH.sub.3OSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 SCN CH.sub.2 CH.sub.3 OCH.sub.3R.sub.1 --A CH.sub.2 CN CH.sub.3 OCH.sub.3R.sub.1 --A CH.sub.2 SCN CH.sub.3 CH.sub.2 CH.sub.3R.sub.1 --B CH.sub.2 P(O)(OCH.sub.3).sub.2 CH.sub.3 OCH.sub.3R.sub.1 --C CH.sub.2 CN CH.sub.3 OCH.sub.3F CH.dbd.NOH CH.sub. 3 OCH.sub.3OCH.sub.3 CH.dbd.NOHCH.sub.3 CH.sub.3 CH.sub.3COOCH.sub.3 C(CH.sub.3).dbd.NOH CH.sub.2 CH.sub.3 OCH.sub.3CO.sub.2 N(CH.sub.3).sub.2 C(CH.sub.3).dbd.NOCH.sub.3 CH.sub.2 CF.sub.3 CH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.dbd.NOH CH.sub.3 OCH.sub.2 CH.sub.3SO.sub.2 CH.sub.3 CH.dbd.NOCH.sub.3 CH.sub.3 OCH.sub.3OSO.sub.2 CH.sub.2 CH.sub.3 C(CH.sub.3).dbd.NOH CH.sub.2 CF.sub.3 OCH.sub.3R.sub.1 --A C(CH.sub.3).dbd.NOCH.sub.3 CH.sub.2 CH.sub.3 CH.sub.3R.sub.1 --B CH.dbd.NOH CH.sub.3 OCH.sub.3R.sub.1 --C CH.dbd.NOCH.sub.3 CH.sub.3 CH.sub.3__________________________________________________________________________
TABLE VI______________________________________General Formula VIR.sub.1 R.sub.2 X.sub.3 m.p. (.degree.C.)______________________________________F CH.sub.2 CN OCH.sub.3Cl CH.sub.2 SCN OCH.sub.3CF.sub.3 CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2 OCH.sub.3NO.sub.2 CH.sub.2 CN CH.sub.3OCH.sub.3 CH.sub.2 CN OCH.sub.3OCH.sub.3 CH.sub.2 SCN CH.sub.3OCH.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3OCH.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 CH.sub.3CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.3CO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 CN OCH.sub.3SO.sub.2 NHCH.sub.3 CH.sub.2 CN CH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 CN OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 SCN CH.sub.3SO.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3SO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.3SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3OSO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 CH.sub.3OSO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3OSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3R.sub.1 --A CH.sub.2 CN CH.sub.3R.sub.1 --A CH.sub.2 SCN OCH.sub.3R.sub.1 --B CH.sub.2 P(O)(OCH.sub.3).sub.2 CH.sub.3R.sub.1 --C CH.sub.2 CN OCH.sub.3F CH.dbd.NOH OCH.sub.3OCH.sub.3 CH.dbd.NOCH.sub.3 OCH.sub.3COOCH.sub.3 C(CH.sub.3).dbd.NOH CH.sub.3CO.sub.2 N(CH.sub.3).sub.2 C(CH.sub.3).dbd.NOCH.sub.3 CH.sub.3SO.sub.2 CH.sub.3 CH.dbd.NOH OCH.sub.3OSO.sub.2 CH.sub.2 CH.sub.3 C(CH.sub.3).dbd.NOCH.sub.3 OCH.sub.3R.sub.1 --A C(CH.sub.3).dbd.NOH OCH.sub.3R.sub.1 --B C(CH.sub.3).dbd.NOCH.sub.3 CH.sub.3R.sub.1 --C CH.dbd.NOH OCH.sub.3______________________________________
TABLE VII______________________________________General Formula VIIR.sub.1 R.sub.2 X.sub.4 Y.sub.4 m.p. (.degree.C.)______________________________________F CH.sub.2 CN CH.sub.3 OCH.sub.3Cl CH.sub.2 SCN OCH.sub.3 CH.sub.3CF.sub.3 CH.sub.2 P(O)(OCH.sub.2 CH.sub.3).sub.2 OCH.sub.2 CH.sub.3 OCH.sub.3NO.sub.2 CH.sub.2 CN CH.sub.2 OCH.sub.3 OCH.sub.3OCH.sub.3 CH.sub.2 CN Cl OCH.sub.3OCH.sub.3 CH.sub.2 SCN CH.sub.3 OCH.sub.2 CH.sub.3OCH.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3 OCH.sub.3OCH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 ClCO.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3 CH.sub.3CO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.2 CH.sub.3 OCH.sub.3CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 OCH.sub.3CO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.2 CH.sub.3CO.sub.2 N(CH.sub.3).sub.2 CH.sub. 2 CN CH.sub.2 OCH.sub.3 OCH.sub.3SO.sub.2 NHCH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 CN OCH.sub.3 OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 CH.sub.2 SCN Cl OCH.sub.3SO.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3 CH.sub.3SO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.3SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.3SO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 CH.sub.3 OCH.sub.3OSO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 OCH.sub.2 CH.sub.3OSO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.3OSO.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.2 CH.sub.3 OCH.sub.3R.sub.1 --A CH.sub.2 CN OCH.sub.3 OCH.sub.3R.sub.1 --A CH.sub.2 SCN OCH.sub.3 CH.sub.3R.sub.1 --B CH.sub.2 P(O)(OCH.sub.3).sub.2 CH.sub.2 OCH.sub.3 OCH.sub.3R.sub.1 --C CH.sub.2 CN OCH.sub.3 OCH.sub.3F CH.dbd.NOH CH.sub.3 OCH.sub.3OCH.sub.3 CH.dbd.NOCH.sub.3 OCH.sub.3 CH.sub.3COOCH.sub.3 C(CH.sub.3).dbd.NOH OCH.sub.2 CH.sub.3 OCH.sub.3CO.sub.2 N(CH.sub.3).sub.2 C(CH.sub.3).dbd.NOCH.sub.3 CH.sub.2 OCH.sub.3 OCH.sub.3SO.sub.2 CH.sub.3 CH.dbd.NOH.sub.3 Cl OCH.sub.3OSO.sub.2 CH.sub.2 CH.sub.3 C(CH.sub.3).dbd.NOCH.sub.3 CH.sub.3 OCH.sub.2 CH.sub.3R.sub.1 --A C(CH.sub.3).dbd.NOH OCH.sub.3 OCH.sub.3R.sub.1 --B CH(CH.sub.3).dbd.NOCH.sub.3 OCH.sub.3 ClR.sub.1 --C CH.dbd.NOH CH.sub.3 OCH.sub.3______________________________________
FORMULATIONS
Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solution, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
______________________________________ Weight Percent* Active Ingredient Diluent(s) Surfactant(s)______________________________________Wettable Powders 20-90 0-74 1-10Oil Suspensions, 3-50 40-95 0-15Emulsions, Solutions,(including EmulsifiableConcentrates)Aqueous Suspension 10-50 40-84 1-20Dusts 1-25 70-99 0-5Granules and Pellets 0.1-95 5-99.9 0-15High Strength 90-99 0-10 0-2Compositions______________________________________ *Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.
Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, N.Y., 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0.degree. C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growthk, etc.
The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solids compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1963, pp. 8-57ff.
For further information regarding the art of formulation, see for example:
H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;
R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;
G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and
J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
In the following examples, all parts are by weight unless otherwise indicated.
EXAMPLE 10
______________________________________High Strength Concentrate______________________________________5-(cyanomethyl)-2-methoxy-N--[(4-methoxy- 99%6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-benzenesulfonamidetrimethylnonyl polyethylene glycol ether 1%______________________________________
The surfactant is sprayed upon the active ingredient in a blender and the mixture sifted through a U.S.S. no. 40 sieve (0.42 mm openings) prior to packaging. The concentrate may be formulated further for practical use.
EXAMPLE 11
______________________________________Wettable Powder______________________________________5-(cyanomethyl)-N--[(4,6-dimethoxypyrimidin- 65%2-yl)aminocarbonyl]-2-methoxybenzene-sulfonamidedodecylphenol polyethylene glycol ether 2%sodium ligninsulfonate 4%sodium silicoaluminate 6%montmorillonite (calcined) 23%______________________________________
The ingredients are thoroughly blended. The liquid surfactant is added by spraying upon the solid ingredients in the blender. After grinding a hammer mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
EXAMPLE 12
______________________________________Aqueous Suspension______________________________________5-(cyanomethyl)-2-methoxy-N--[(4-methoxy- 50.0%6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-benzenesulfonamidepolyacrylic acid thickener 0.3%dodecylphenol polyethylene glycol ether 0.5%disodium phosphate 1%monosodium phosphate 0.5%polyvinyl alcohol 1.0%water 56.7%______________________________________
The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
EXAMPLE 13
______________________________________Oil Suspension______________________________________5-(cyanomethyl)-2-methoxy-N--[(4-methoxy- 35%6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-benzenesulfonamideblend of polyalcohol carboxylic esters 6%and oil soluble petroleum sulfonatesxylene 59%______________________________________
The ingredients are combined and ground together in a sand mill to produce particles essentially all below 3 microns. The product can be used directly, extended with oils, or emulsified in water.
EXAMPLE 14
______________________________________Oil Suspension______________________________________5-(cyanomethyl)-N--[(4,6-dimethoxypyrimidin 25%2-yl)aminocarbonyl]-2-methoxybenzene-sulfonamide.polyoxyethylene sorbitol hexaoleate 5%highly aliphatic hydrocarbon oil 70%______________________________________
The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.
EXAMPLE 15
______________________________________Aqueous Suspension______________________________________5-(cyanomethyl)-N--[(4,6-dimethoxypyrimidin- 25%2-yl)-aminocarbonyl]-2-methoxybenzene-sulfonamidehydrated attapulgite 3%crude calcium ligninsulfonate 10%sodium dihydrogen phosphate 0.5%water 61.5%______________________________________
The ingredients are ground together in a ball or roller mill until the solid particles have been reduced to diameters under 10 microns.
EXAMPLE 16
______________________________________Wettable Powder______________________________________5-(cyanomethyl)-2-methoxy-N[(4-methoxy- 40%6-methyl-1,3,5-triazin-2-yl)amino-carbonyl]benzenesulfonamidedioctyl sodium sulfosuccinate 1.5%sodium ligninsulfonate 3%low viscosity methyl cellulose 1.5%attapulgite 54%______________________________________
The ingredients are thoroughly blende, passed thrugh an air mill, to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.
All compounds of the invention may be formulated in the same manner.
EXAMPLE 17
______________________________________Granule______________________________________wettable powder of Example 16 15%gypsum 69%potassium sulfate 16%______________________________________
The ingredients are blended in a rotating mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 cm (U.S.S. #18 to 40 sieves), the granules are removed, dried, and screened. Oversized material is crushed to produce additional material in the desired range. These granules contain % active ingredient.
EXAMPLE 18
______________________________________Wettable Powder______________________________________5-(cyanomethyl)-N--[(4,6-diemthoxyprimidin- 50%2-yl)-aminocarbonyl]-2-methoxybenzene-sulfonamidesodium alkylnaphthalenesulfonate 2%low viscosity methyl cellulose 2%diatomaceous earth 46%______________________________________
The ingredients are blended, coarsely hammermilled and the air milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.
EXAMPLE 19
______________________________________Extruded Pellet______________________________________5-(cyanomethyl)-N--[(4,6-dimethoxypyrimidin- 25%2-yl)aminocarbonyl]-2-methoxybenzene-sulfonamideanhydrous sodium sulfate 10%crude calcium ligninsulfonate 5%sodium alkylnaphthalenesulfonate 1%calcium/magnesium bentonite 59%______________________________________
The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
EXAMPLE 20
______________________________________Wettable Powder______________________________________5-(cyanomethyl)-2-methoxy-N--[(4-methoxy-6- 80%methyl-1,3,5-triazin-2-yl)aminocarbonyl]-benzenesulfonamidesodium alkylnaphthalenesulfonate 2%sodium ligninsulfonate 2%synthetic amorphous silica 3%kaolinite 13%______________________________________
The ingredients are blended and then ground in a hammermill to produce particles with an average particle size less than 25 microns in diameter. The material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before being packaged.
EXAMPLE 21
______________________________________High Strength Concentrate______________________________________5-(cyanomethyl)-N--[(4,6-dimethoxypyrimidin- 98.5%2-yl)-aminocarbonyl]-2-methoxybenzene-sulfonamidesilica aerogel 0.5%synthetic amorphous fine silica 1.0%______________________________________
The ingredients are blended and ground in a hammer mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways.
UTILITY
Test results indicate that the compounds of the present invention are highly active preemergent or postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Some of the compounds have utility for selective weed control in crops such as wheat. Alternatively, the subject compounds are useful to modify plant growth.
The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage pre-sent, etc. In generaly terms, the subject compounds should be applied at levels of around 0.001 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required.
The compounds of the invention may be used in combination with any other commercial herbicide; examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.
The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.
TEST A
Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusgalli), cheatgrass (Bromus Secalinus), giant foxtail (Setaria faberii), wild oats (Avena fatua), velvetleaf (Aubutilon theophrasti), moringglory (Ipomoea spp., cocklebur (Xanthium pensylvanicum), sorghum, corn, barley, soybean, sugarbeet, cotton, rice, wheat and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:
B=burn;
C=chlorosis/necrosis;
D=defoliation;
E=emergence inhibition;
G=growth retardation;
H=formative effect;
U=unusual pigmentation;
X=axillary stimulation;
S=albinism; and
6Y=abscised buds or flowers.
COMPOUNDS__________________________________________________________________________ ##STR58##Compound R.sub.1 R.sub.2 X Y Z__________________________________________________________________________1 OCH.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.3 CH2 OCH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.3 N3 CO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 CH4 CO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH5 CO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 OCH.sub.3 N6 CO.sub.2 CH.sub.3 CH.sub.2 P(O)(OCH.sub.3).sub.2 OCH.sub.3 CH.sub.3 N7 CO.sub.2 CH.sub.3 CH.sub.2 SCN OCH.sub.3 OCH.sub.3 CH8 CO.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.3 CH9 CO.sub.2 CH.sub. 3 CH.sub.2 CN OCH.sub.3 CH.sub.3 N10 OCH.sub.3 CH.sub.2 N.sub.3 OCH.sub.3 OCH.sub.3 CH11 OCH.sub.3 CH.sub.2 N.sub.3 OCH.sub.3 CH.sub.3 CH12 OCH.sub.3 CH.sub.2 N.sub.3 CH.sub.3 CH.sub.3 CH13 OCH.sub.3 CH.sub.2 N.sub.3 OCH.sub.3 Cl CH14 OCH.sub.3 CH.sub.2 N.sub.3 OCH.sub.3 OCH.sub.3 N15 OCH.sub.3 CH.sub.2 N.sub.3 OCH.sub.3 CH.sub.3 N16 OC.sub.2 H.sub.5 C(O)CH.sub.3 OCH.sub.3 OCH.sub.3 CH17 OC.sub.2 H.sub.5 C(O)CH.sub.3 OCH.sub.3 CH.sub.3 CH18 OC.sub.2 H.sub.5 C(O)CH.sub.3 CH.sub.3 CH.sub.3 CH19 OC.sub.2 H.sub.5 C(O)CH.sub.3 OCH.sub.3 OCH.sub.3 N20 OC.sub.2 H.sub.5 C(O)CH.sub.3 OCH.sub.3 CH.sub.3 N21 COOCH(CH.sub.3).sub.2 CH.sub.2 N.sub.3 OCH.sub.3 OCH.sub.3 CH22 COOCH(CH.sub.3).sub.2 CH.sub.2 N.sub.3 OCH.sub.3 CH.sub.3 CH23 COOCH(CH.sub.3).sub.2 CH.sub.2 N.sub.3 CH.sub.3 CH.sub.3 CH24 COOCH(CH.sub.3).sub.2 CH.sub.2 N.sub.3 Cl OCH.sub.3 CH25 COOCH(CH.sub.3).sub.2 CH.sub.2 N.sub.3 OCH.sub.3 OCH.sub.3 N26 COOCH(CH.sub.3).sub.2 CH.sub.2 N.sub.3 OCH.sub.3 CH.sub.3 N27 Cl CH.sub.2 SCN CH.sub.3 OCH.sub.3 CH28 Cl CH.sub.2 N.sub.3 OCH.sub.3 OCH.sub.3 CH29 Cl CH.sub.2 N.sub.3 CH.sub.3 OCH.sub.3 CH30 Cl CH.sub.2 N.sub.3 CH.sub.3 CH.sub.3 CH31 Cl CH.sub.2 N.sub.3 Cl OCH.sub.3 CH32 Cl CH.sub.2 N.sub.3 OCH.sub.3 OCH.sub.3 N33 Cl CH.sub.2 N.sub.3 OCH.sub.3 CH.sub.3 N34 SO.sub.2 CH.sub.3 C(O)H OCH.sub.3 OCH.sub.3 CH35 SO.sub.2 CH.sub.3 CH.sub.2 N.sub.3 OCH.sub.3 OCH.sub.3 CH36 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 OCH.sub.3 OCH.sub.3 CH37 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 CH.sub.3 OCH.sub.3 CH38 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.3 N.sub.3 OCH.sub.3 CH.sub.3 N39 COOCH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.3 CH40 COOCH.sub.3 CH.sub.2 CN CH.sub.3 CH.sub.3 CH41 COOCH.sub.3 CH.sub.2 CN Cl OCH.sub.3 CH42 COOCH.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.3 N43 COOCH.sub.2 CH.sub.3 C(O)H OCH.sub.3 OCH.sub.3 CH44 COOCH.sub.2 CH.sub.3 C(O)H CH.sub.3 CH.sub.3 CH45 COOCH.sub.2 CH.sub.3 C(O)H Cl OCH.sub.3 CH46 COOCH.sub.2 CH.sub.3 C(O)H OCH.sub.3 CH.sub.3 N47 COOCH(CH.sub.3).sub.2 CH.sub.2 CN OCH.sub.3 OCH.sub.3 CH48 COOCH(CH.sub.3).sub.2 CH.sub.2 CN CH.sub.3 CH.sub.3 CH49 COOCH.sub.3 C(O)H OCH.sub.3 OCH.sub.3 CH50 COOCH.sub.3 C(O)H OCH.sub.3 CH.sub.3 CH51 COOCH.sub.3 C(O)H CH.sub.3 CH.sub.3 CH52 COOCH.sub.3 C(O)H Cl OCH.sub.3 CH53 COOCH.sub.3 C(O)H OCH.sub.3 CH.sub.3 N54 COOCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 OCH.sub.3 OCH.sub.3 CH55 COOCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 OCH.sub.3 CH.sub.3 CH56 COOCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 CH.sub.3 CH.sub.3 CH57 COOCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 Cl OCH.sub.3 CH58 COOCH.sub.2 CH.sub. 2 CH.sub.3 CH.sub.2 N.sub.3 OCH.sub.3 OCH.sub.3 N59 COOCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 N.sub.3 OCH.sub.3 CH.sub.3 N60 COOCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.3 CH61 COOCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.3 CH62 COOCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN CH.sub.3 CH.sub.3 CH63 COOCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN Cl OCH.sub.3 CH64 COOCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 OCH.sub.3 N65 COOCH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CN OCH.sub.3 CH.sub.3 N66 OCH.sub.2 CH.sub.2 C(CH.sub.3)NOH OCH.sub.3 OCH.sub.3 CH67 OCH.sub.2 CH.sub.3 C(CH.sub.3)NOH OCH.sub.3 CH.sub.3 CH68 OCH.sub.2 CH.sub.3 C(CH.sub.3)NOH Cl OCH.sub.3 CH69 OCH.sub.2 CH.sub.3 C(CH.sub.3)NOH OCH.sub.3 OCH.sub.3 N70 OCH.sub.2 CH.sub.3 C(CH.sub.3)NOH OCH.sub.3 CH.sub.3 N71 OCH.sub.2 CH.sub.3 C(CH.sub.3)NOCH.sub.3 OCH.sub.3 OCH.sub.3 CH72 COOCH.sub.3 CHNOCH.sub.3 OCH.sub.3 OCH.sub.3 CH73 COOCH.sub.3 CHNOCH.sub.3 OCH.sub.3 CH.sub.3 CH74 COOCH.sub.3 CHNOCH.sub.3 CH.sub.3 CH.sub.3 CH75 COOCH.sub.3 CHNOCH.sub.3 Cl OCH.sub.3 CH76 COOCH.sub.3 CHNOCH.sub.3 OCH.sub.3 OCH.sub.3 N77 COOCH.sub.3 CHNOCH.sub.3 OCH.sub.3 CH.sub.3 N__________________________________________________________________________
TABLE A______________________________________ Compound 1 Compound 2Rate kg/ha 0.05 0.05______________________________________POST-EMERGENCEMorningglory 10C 4C,8HCocklebur 9C 4C,9GVelvetleaf 9C 2C,5GNutsedge 2C,8G 2C,5GCrabgrass 2C,9G 2C,7GBarnyardgrass 3C,9H 4C,9HCheatgrass 9G 6GWild Oats 3C,9G 3C,9GWheat 8G 9GCorn 5C,9H 3C,9GSoybean 5C,9G 4C,9GRice 5C,9G 6C,9GSorghum 4C,9H 5C,9HSugar beet 9C 9CCotton 9C 5C,9GPRE-EMERGENCEMorningglory 9G 9GCocklebur 8H 9HVelvetleaf 9G 3GNutsedge 3C,8G 0Crabgrass 0 0Barnyardgrass 4C,9H 5GCheatgrass 8G 5GWild Oats 3C,8G 3C,8GWheat 3C,9G 3C,9HCorn 3C,9G 2C,9HSoybean 8H 3C,5HRice 3C,9H 5C,9HSorghum 10E 9HSugar beet 7G 4C,7GCotton 8G 6G______________________________________ Compound 3 Compound 4Rate kg/ha 0.05 0.05______________________________________POST-EMERGENCEMorningglory 10C 3C,9GCocklebur 10C 2C,7GVelvetleaf 10C 3C,7HNutsedge 4C,9G 5GCrabgrass 3C,7G 3GBarnyardgrass 6C,9H 4C,9HCheatgrass 6C,9G 5C,9GWild Oats 5C,9G 5C,9GWheat 7G 8GCorn 4U,9C 5C,9GSoybean 9C 4C,9GRice 5C,9G 5C,9GSorghum 9C 4C,9GSugar beet 9C 5C,8HCotton 9C 4C,7HPRE-EMERGENCEMorningglory 9G 8GCocklebur 9H 5GVelvetleaf 9C --Nutsedge 4C,8G 0Crabgrass 2C,8G 7GBarnyardgrass 3C,8G 2HCheatgrass 4C,9H 2C,5GWild Oats 4C,8G 3C,6GWheat 6G 5GCorn 3C,9G 4GSoybean 3C,5H 3GRice 4C,8H 2CSorghum 4C,9H 3C,5GSugar beet 10C 4C,8HCotton 2C,8G 8G______________________________________ Compound 5 Compound 6Rate kg/ha 0.05 0.05______________________________________POST-EMERGENCEMorningglory 2C,3H 2C,2GCocklebur 2G 2GVelvetleaf 2H 2GNutsedge 0 0Crabgrass 0 lHBarnyardgrass 0 2HCheatgrass 0 0Wild Oats 0 0Wheat 0 0Corn 0 2HSoybean 1H 3HRice 2G 5GSorghum 0 5GSugar beet 1H 3HCotton 0 0PRE-EMERGENCEMorningglory 5G 2GCocklebur 0 0Velvetleaf 0 0Nutsedge 0 0Crabgrass 4G 2GBarnyardgrass 0 0Cheatgrass 2G 0Wild Oats 0 0Wheat 0 2GCorn 0 2GSoybean 2G 4HRice 0 2GSorghum 0 0Sugar beet 0 0Cotton -- --______________________________________ Compound 7 Compound 8Rate kg/ha 0.05 0.05______________________________________POST-EMERGENCEMorningglory 10C 10CCocklebur 9C 10CVelvetleaf 10C 10CNutsedge 9G 9CCrabgrass 8G 4C,9GBarnyardgrass 4C,9H 9CCheatgrass 4C,9G 9CWild Oats 6C,9G 9CWheat 4C,9G 9CCorn 4U,9G 7U,9CSoybean 5C,9G 9CRice 9C 9CSorghum 9C 9CSugar beet 9C 9CCotton 9C 9CPRE-EMERGENCEMorningglory 9G 9GCocklebur 10H 9HVelvetleaf 9C 9GNutsedge 4C,9G 10ECrabgrass 4C,8G 4C,9GBarnyardgrass 4C,9G 4C,9HCheatgrass 4C,8H 4C,9GWild Oats 3C,8G 5C,9GWheat 5G 10ECorn 8G 4C,9HSoybean 2G 8HRice 9H 10ESorghum 2C,9G 10ESugar beet 10C 4C,9GCotton 9C 9G______________________________________ Compound 9 Compound 10Rate kg/ha 0.05 0.05______________________________________POST-EMERGENCEMorningglory 10C 4GCocklebur 10C 7GVelvetleaf 10C 4C,9GNutsedge 5C,9G 4C,9GCrabgrass 2C,8G 2C,5GBarnyardgrass 9C 3C,8HCheatgrass 6C,9G 2C,8GWild Oats 9C 3C,5GWheat 9C 6GCorn 7U,9C 3C,9HSoybean 9C 5C,9GRice 9C 2C,9GSorghum 9C 3C,9HSugar beet 9C 9CCotton 2C,9G 4C,9GPRE-EMERGENCEMorningglory 4C,9G 9GCocklebur 3C,9H 8GVelvetleaf 4C,9G 8GNutsedge 10E 4GCrabgrass 3C,7G 3GBarnyardgrass 5C,9H 3C,8HCheatgrass 4C,8H 8HWild Oats 5C,9G 3C,8GWheat 5C,9G 7GCorn 3C,9G 2C,7GSoybean 2C,5H 3C,5HRice 10E 2C,8GSorghum 5C,9H 3C,9HSugar beet 10C 9CCotton 8G 9G______________________________________ Compound 11 Compound 12Rate kg/ha 0.05 0.05______________________________________POST-EMERGENCEMorningglory 3C,8H 0Cocklebur 7H 2HVelvetleaf 3C,8H 3GNutsedge 2C,9G 0Crabgrass 5G 0Barnyardgrass 3C,9H 0Cheatgrass 9G 0Wild Oats 3C,5G 0Wheat 9G 0Corn 9G 2C,7HSoybean 4C,9G 3C,8GRice 5C,9G 6GSorghum 9H 6GSugar beet 3C,8G 2HCotton 3C,9G 2C,2GPRE-EMERGENCEMorningglory 8G 0Cocklebur 8H 8HVelvetleaf 4C,9G 3GNutsedge 5G 0Crabgrass 4G 0Barnyardgrass 9H 0Cheatgrass 3C,9H 0Wild Oats 3C,9G 0Wheat 9G 0Corn 2C,9G 0Soybean 4C,8H 2C,2HRice 8H 0Sorghum 10E 0Sugar beet 4C,9G 8GCotton 9G 3G______________________________________ Compound 13 Compound 14Rate kg/ha 0.05 0.05______________________________________POST-EMERGENCEMorningglory 2C,4G 3C,9GCocklebur 5G 5C,9GVelvetleaf 0 2C,6HNutsedge 2C,4G 0Crabgrass 0 2GBarnyardgrass 0 2C,3HCheatgrass 0 0Wild Oats 0 2GWheat 0 3GCorn 0 3C,8HSoybean 3H 5C,9GRice 5G 2C,8GSorghum 2C,5G 3C,8HSugar beet 3C,5G 4C,9GCotton 3C,7G 2C,5GPRE-EMERGENCEMorningglory 8G 7HCocklebur -- 9HVelvetleaf 5G 4GNutsedge 5G 0Crabgrass 2G 0Barnyardgrass 0 1CCheatgrass 0 2GWild Oats 0 2C,4GWheat 0 6GCorn 5G 2C,6GSoybean 2C,2G 6HRice 2C 8GSorghum 2C,4G 2C,7HSugar beet 6G 10CCotton 6G 2G______________________________________ Compound 15 Compound 16Rate kg/ha 0.05 0.4 0.05______________________________________POST-EMERGENCEMorningglory 4C,8H 10C 1C,1HCocklebur 9H 10C 3C,9HVelvetleaf 4C,8H 9C 5C,9GNutsedge 0 5C,9G 4C,9GCrabgrass 4G 4C,9G 3GBarnyardgrass 4C,8H 6C,9H 3C,9HCheatgrass 2C,5G 2C,8G 2GWild Oats 3C,9G 3C,9G 4GWheat 6G 5C,9G 5GCorn 4C,9H 4C,9G 2C,9HSoybean 5C,9G 5C,9G 2C,7GRice 5C,9G 5C,9G 4C,9GSorghum 3C,9H 3C,9H 5C,9GSugar beet 9C 9C 3C,6GCotton 4C,8G 9C 5C,9GPRE-EMERGENCEMorningglory 7G 9G 8GCocklebur 7H 8H 9HVelvetleaf 5H 5C,9G 9GNutsedge 4G 7G 2C,7GCrabgrass 0 5G 0Barnyardgrass 2C,5G 3C,9H 3C,9HCheatgrass 6G 3C,8H 3C,6GWild Oats 2C,8G 5C,9G 3C,8GWheat 2C,9G 9C 7GCorn 3C,9G 9G 9GSoybean 3C,6H 9H 3C,4GRice 2C,8H 10E 4C,8HSorghum 3C,9H 5C,9H 4C,9HSugar beet 4C,9G 9C 4C,8GCotton 7G 9G 7G______________________________________ Compound 17 Compound 18Rate kg/ha 0.05 0.05______________________________________POST-EMERGENCEMorningglory 3G 1HCocklebur 5C,9H 6GVelvetleaf 4C,9G 6HNutsedge 3C,6G 0Crabgrass 3C,4G 0Barnyardgrass 3C,9H 1C,2HCheatgrass 4G 0Wild Oats 0 0Wheat 2G 0Corn 3C,9H 3C,7HSoybean 3C,7G 2HRice 2C,8G 5GSorghum 4C,9H 2C,5GSugar beet 4G 2GCotton 9C 4GPRE-EMERGENCEMorningglory 9G 2HCocklebur 8H 7HVelvetleaf 4C,9G 4GNutsedge 5G 0Crabgrass 4G 0Barnyardgrass 3C,9H 2CCheatgrass 3C,7G 0Wild Oats 3C,8G 0Wheat 3C,9G 0Corn 3C,9H 3C,6GSoybean 3C,7H 1CRice 4C,8H 2C,5GSorghum 3C,9H 5GSugar beet 4C,9G 9GCotton 8G 5G______________________________________ Compound 19 Compound 20Rate kg/ha 0.05 0.05______________________________________POST-EMERGENCEMorningglory 3G 0Cocklebur 4C,9G 4C,9GVelvetleaf 2C,7G 2C,5GNutsedge 0 5GCrabgrass 4G 4GBarnyardgrass 3C,7H 3C,8HCheatgrass 0 0Wild Oats 0 0Wheat 0 0Corn 3C,9H 4C,9GSoybean 2C,5H 3H,5GRice 2C,9G 5C,9GSorghum 3C,8G 4C,9HSugar beet 3C,4H 3C,6HCotton 3C,5G 3C,5GPRE-EMERGENCEMorningglory 8G 6GCocklebur 8H 8GVelvetleaf 7G 5GNutsedge 0 0Crabgrass 0 0Barnyardgrass 5H 3C,7GCheatgrass 0 0Wild Oats 0 0Wheat 0 0Corn 3C,9H 9GSoybean 2C,4G 2C,6GRice 3C,9H 9HSorghum 3C,8H 3C,9HSugar beet 3C,7G 4C,8GCotton 7G 7G______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 21 22 23 24Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 10C 10C 9C 9CCocklebur 10C 9C 10C 9CVelvetleaf 10C 9C 9C 5C,9GNutsedge 5C,9G 4C,9G 4C,9G 2C,8GCrabgrass 0 0 2G 0Giant Foxtail 3C,6G 3C,6G 4C,9G 1HBarnyardgrass 10C 4C,9H 9C 3C,8HCheatgrass 5C,9G 3C,9G 9G 2GWild Oats 2C,5G 0 10C 0Wheat 4C,9G 7G 2C,9G 0Corn 9C 4C,9H 9C 2C,5GBarley 8G 9G 9C 2GSoybean 9C 4C,9G 3C,9G 3H,4GRice 9C 4C,9G 9C 4C,9GSorghum 9C 2C,9H 9C 9HSugar beet 9C 9C 9C 5C,9GCotton 9C 5C,9G 10C 10CPREEMERGENCEMorningglory 9G 9H 7H 9GCocklebur 9H 9H 9H 9HVelvetleaf 10C 9C 8G 8GNutsedge 9G 8G 9G 0Crabgrass 0 2G 2G 0Giant Foxtail 3C,7G 3C,6G 4C,8G 2C,2GBarnyardgrass 4C,9H 4C,9H 4C,8H 2C,5GCheatgrass 3C,9H 9G 9G 4GWild Oats 7G 3C,7G 7G 0Wheat 9H 9G 8G 0Corn 3C,9H 9H 5C,9H 7GBarley 9G 9G 9G 7GSoybean 2C,7H 3C,8H 4C,6H 0Rice 4C,9H 2C,8G 4C,9H 3C,7GSorghum 4C,9H 9H 5C,9H 4C,8HSugar beet 5C,9G 9G 4C,9G 9GCotton 8G 9G 9G 8G______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 25 26 27 28Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 9C 10C 3C,7H 10CCocklebur 10C 10C 0 8HVelvetleaf 5C,9G 10C 0 10CNutsedge 5C,9G 5C,9G 0 6C,9GCrabgrass 2G 0 0 0Giant Foxtail 3C,9G 4C,9G 0 3C,7GBarnyardgrass 3C,8H 4C,9H 5H 4C,9HCheatgrass 7G 2C,9G 0 7GWild Oats 3G 9C 0 0Wheat 4G 4G 0 0Corn 9C 10C 5H 3C,8HBarley 4G 7G 0 2CSoybean 5C,9G 10C 3H 4C,9GRice 9C 9C 0 3C,9GSorghum 3C,9H 9C 3G 7GSugar beet 5C,9G 10C 4C,6G 10CCotton 10C 10C 0 4C,9GPREEMERGENCEMorningglory 8G 9G 5G 7GCocklebur -- -- 8G 9HVelvetleaf 6G 4C,9G 8G 9GNutsedge 8G 10E 0 3GCrabgrass 4G 3G 0 5GGiant Foxtail 2C,5G 3C,5G 0 4C,6GBarnyardgrass 3C,6G 3C,8H 0 4C,7HCheatgrass 6G 9H 0 5GWild Oats 2G 2C,8G 0 2GWheat 4G 3C,9H 0 0Corn 3C,9G 3C,9G 2C,3G 7GBarley 8G 9G 2G 7GSoybean 2C,6G 3C,7H 0 2C,5HRice 8G 9H 4G 2C,6HSorghum 3C,8H 3C,9H 0 2C,4HSugar beet 5C,9G 5C,9G 8G 10CCotton 8G 9G 3G 7G______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 29 30 31 32Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 9C 0 3G 10CCocklebur 9H 4C,9H 4C,9H 10CVelvetleaf 10C 8G 0 2C,5GNutsedge 4C,8G 0 0 5GCrabgrass 0 0 0 0Giant Foxtail 4G 0 0 2C,4GBarnyardgrass 3C,8H 0 4H 3C,9HCheatgrass 2C,5G 0 0 0Wild Oats 2C 0 0 2C,5GWheat 0 0 0 0Corn 9H 0 0 3C,9HBarley 5G 0 0 2GSoybean 3H,9G 7G 2G 4C,9GRice 8G 5G 0 4C,9GSorghum 3C,9H 3C,7H 2G 2C,7GSugar beet 10C 6C,9G 2G 10CCotton 4C,9G 5G 4C,8G 9CPREEMERGENCEMorningglory 7G 5G 7G 8GCocklebur 8H 9H 9H 9HVelvetleaf 9G 9G 9G 9CNutsedge 10E 5G 10E 0Crabgrass 3G 0 0 0Giant Foxtail 4C,7G 5G 4G 8GBarnyardgrass 4C,8H 2G 2G 3C,7GCheatgrass 3C,7G 0 0 4GWild Oats 5G 4G 0 5GWheat 5G 0 0 0Corn 3C,8H 3G 2C,6G 2C,7GBarley 9G 3G 0 2C,8GSoybean 3C,8H 1C 0 3C,5HRice 4C,9H 3G 3G 9HSorghum 3C,5G 5G 5G 5GSugar beet 9C 8G 9G 10CCotton 7G 7G 8G 7G______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 33 34 35 36Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 10C 10C 10C 10CCocklebur 9C 10C 10C 9CVelvetleaf 4C,8G 10C 10C 9CNutsedge 2C,5G 5C,9G 10C 4C,9GCrabgrass 2G 8G 9C 0Giant Foxtail 6G 5C,9G 9C 4GBarnyardgrass 4C,9H 9C 9C 4C,9HCheatgrass 5G 4C,9G 9C 8GWild Oats 3G 4C,8G 4C,9G 0Wheat 3G 9G 9G 3GCorn 3C,9H 5C,9G 6C,9G 2HBarley 0 9C 5C,9G 9GSoybean 4C,9G 6C,9G 5C,9G 3C,9GRice 5C,9G 9C 9C 5C,9GSorghum 4C,9H 9C 9C 4C,9HSugar beet 9C 9C 10C 9CCotton 4C,9G 10C 10C 4C,9GPREEMERGENCEMorningglory 7G 10C 8G 1HCocklebur -- 9H 8H 3HVelvetleaf 6G 9G 8G 5GNutsedge 10E 8G 9G 3GCrabgrass 0 0 3G 0Giant Foxtail 0 4C,9H 3C,8G 2GBarnyardgrass 2C,7G 4C,9H 3C,9H 7GCheatgrass 0 9H 9H 3GWild Oats 2G 2C,8G 3C,8G 0Wheat 0 6C,9H 10H 0Corn 2C,5G 9H 5C,9H 3C,7GBarley 2G 9G 9G 9GSoybean 3C,3H 7H 3C,7G 2HRice 7G 10E 10E 8HSorghum 3C,3H 5C,9H 10H 3C,7GSugar beet 8G 9G 8G 7HCotton 6G 9G 9G 2G______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 37 38 39 40Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 5C,9G 3C,8G 10C 10CCocklebur 4C,9H 4C,9G 10C 10CVelvetleaf 5C,9G 4C,9H 10C 10CNutsedge 5G 2G 9C 10CCrabgrass 0 0 9C 5C,9GGiant Foxtail 2G 2G 10C 9CBarnyardgrass 3C,8H 2C,5H 9C 9CCheatgrass 8G 0 9C 9CWild Oats 2G 0 9C 9CWheat 3G 0 9C 2C,9GCorn 0 3C,9H 9C 5C,9GBarley 4C,9G 0 9C 9CSoybean 4C,9G 2C,7H 9C 9CRice 4C,8G 3C,8G 9C 9CSorghum 2C,7G 3C,8H 9C 9CSugar beet 3C,7H 5C,9G 9C 9CCotton 4C,9H 4C,8H 10C 10CPREEMERGENCEMorningglory 3G 7H 10E 9HCocklebur 9H 7H 9H 9CVelvetleaf 7H 7G 10E 9CNutsedge 0 0 10E 10CCrabgrass 0 0 5C,9G 5C,9GGiant Foxtail 3G 1C 9C 5C,9HBarnyardgrass 7H 2C 5C,9H 5C,9HCheatgrass 6G 0 10E 10EWild Oats 2G 0 6C,9H 5C,9HWheat 3G 0 10E 10ECorn 2C,6G 6G 10E 5C,9HBarley 3C,9G 3G 4C,9G 5C,9HSoybean 2C,5G 2C 9H 9HRice 3C,7H 2C,5G 10H 10ESorghum 4C,9H 2C,5G 10H 10ESugar beet 5H 5G 9C 5C,9GCotton 0 6G 9C 10C______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 41 42 43 44Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 10C 10C 10C 5C,9HCocklebur 10C 10C 10C 2C,8HVelvetleaf 9C 6G 3C,8G 2H,5GNutsedge 9C 9C 2C,8G 2C,8GCrabgrass 4C,8G 3C,7G 2G 0Giant Foxtail 9C 3C,8G 1C,6G 0Barnyardgrass 9C 9C 9C 4C,9HCheatgrass 4C,9G 2C,9G 1C,5G 3GWild Oats 5C,9G 9G 0 0Wheat 9C 2C,9G 0 0Corn 5C,9G 10C 4C,9G 3C,9GBarley 4C,9G 9C 6G 2C,9GSoybean 9C 9C 2C,8H 2C,7HRice 9C 9C 4C,9G 3C,9GSorghum 9C 3C,9G 3C,9G 3C,9GSugar beet 9C 9C 2C,4G 2C,6GCotton 10C 9C 9C 3C,8GPREEMERGENCEMorningglory 9G 9G 7G 4GCocklebur 9H 8H 9H 2C,7GVelvetleaf 10C 8G 2C,4G 4GNutsedge 10E 10E 9G 7GCrabgrass 3G 2C,5G 9G 2C,8GGiant Foxtail 3C,9H 3C,8G 2C,4G 2C,5GBarnyardgrass 3C,9H 8H 9H 2C,7HCheatgrass 8G 7G 4G 2GWild Oats 6C,9H 4C,9G 5G 2GWheat 4C,9H 4C,9H 4G 0Corn 9H 4C,9H 2C,9H 5C,9HBarley 3C,9H 4C,9H 7G 6GSoybean 9H 4C,8H 2C,7H 2C,5HRice 10E 10E 4C,9H 5C,9HSorghum 10H 5C,9H 2C,9H 3C,9HSugar beet 5C,9G 4C,9G 2C,4G 2C,4GCotton 9G 9G 9G 2C,6G______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 45 46 47 48Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 5C,9G 5C,8H 10C 10CCocklebur 2C,6G 4C,9H 10C 10CVelvetleaf 0 2G 5C,9G 3C,8GNutsedge 0 0 4C,9G 2C,9GCrabgrass 2G 1C,3G 2C,4G 7GGiant Foxtail 0 2C,5G 5C,9H 4C,9GBarnyardgrass 8H 9C 9C 9CCheatgrass 2G 2C 2C,5G 4C,9GWild Oats 0 0 2C,6G 3C,9GWheat 0 0 6G 4C,9GCorn 2C,4H 9G 4U,9G 4U,9GBarley 0 0 3C,8H 4C,9GSoybean lC,lH 2H 9C 9CRice 2G 5C,9G 5C,9G 6C,9GSorghum 8G 2C,8H 9C 6C,9GSugar beet 0 3C,7H 10C 9CCotton 3C,8G 2C,6G 10C 9CPREEMERGENCEMorningglory 2C,5G 0 9G 8GCocklebur 2C,5H 0 9H 8HVelvetleaf 0 0 3C,7G 8GNutsedge 3C,8G 0 5G 3C,9GCrabgrass 0 0 0 3GGiant Foxtail 0 0 3C,7G 8GBarnyardgrass 3C,8H 2C,8H 9H 3C,9HCheatgrass 0 0 8G 8GWild Oats 0 0 6G 8GWheat 0 0 7G 9HCorn 2C,8H 0 3C,9G 3C,9GBarley 7G 0 7G 9GSoybean 0 0 7H 3C,7HRice 2C,8H 0 3C,9H 9HSorghum 2C,9H 0 9H 9HSugar beet 0 0 3C,9G 9GCotton 1C,3G 0 8G 9G______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 49 50 51 52Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 10C 9C 9C 6GCocklebur 9C 4C,9G 9C 4C,9HVelvetleaf 10H 3C,6G 3C,5H 2HNutsedge 4G 4G 5G 4GCrabgrass 2C,7G 4G 4G 3GGiant Foxtail 9C 3C,7H 4C,9G 6GBarnyardgrass 9C 9C 9C 9CCheatgrass 6G 4G 5G 0Wild Oats 2C,4G 0 0 0Wheat 3G 3G 2G 0Corn 4C,9H 2C,8G 3C,9G 2C,9HBarley 4C,9G 3C,7G 2C,7G 6GSoybean 9C 5C,9G 5C,9G 3C,7HRice 9C 9C 9C 9CSorghum 9C 3C,8G 9H 4C,9GSugar beet 10C 5C,9G 2C,6G 3C,5HCotton 10C 10C 10C 10CPREEMERGENCEMorningglory 8H 1H 7H 0Cocklebur 9H 0 2C,2H 1HVelvetleaf 4G 2G 2G 0Nutsedge 7G 0 4G 8GCrabgrass -- 5G 8G 8GGiant Foxtail 6G 3G 4G 0Barnyardgrass 9H 3C,9H 4G 9HCheatgrass 2C,7G 7G 0 0Wild Oats 8G 4G 6G 4GWheat 5G 6G 7G 4GCorn 3C,9G 2C,7G 2C,6G 2C,3GBarley 2C,9G 2G 4G 2C,5GSoybean 3C,9H 3C,8H 3C,8H 2C,3HRice 5C,9H 9H 9H 5C,9HSorghum 9H 9H 9H 9HSugar beet 9G 4H 7G 3GCotton 9G 8G 3C,9G 8G______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 53 54 55 56Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 3C,8H 10C 10C 6C,9GCocklebur 3C,8H 10C 9H 2C,9HVelvetleaf 2C,3H 10C 9C 10CNutsedge 0 3C,9G 2C,9G 2C,7GCrabgrass 8G 0 3G 3GGiant Foxtail 3C,9G 5G 2C,9G 7GBarnyardgrass 5C,9H 4C,9G 4C,8G 1C,7GCheatgrass 7G 3C,9G 3C,9G 8GWild Oats 0 3G 2C,5G 2C,6GWheat 3G 8G 9G 7GCorn 2C,9H 9G 2C,9G 3C,9HBarley 2C,5G 9G 8G 8GSoybean 8G 3C,9G 3C,9H 2C,8GRice 9C 2C,9G 9G 2C,9GSorghum 4C,9G 9G 2C,9G 2C,9GSugar beet 8G 9C 9C 9CCotton 3C,5G 9C 9C 10CPREEMERGENCEMorningglory 0 0 7G 3HCocklebur 0 3H -- 2C,3HVelvetleaf 0 1C,5G 4C,7G 2C,7GNutsedge 0 7G 3C,9G 7GCrabgrass 0 2G 0 0Giant Foxtail 0 2G 7G 2GBarnyardgrass 0 3C,7H 2C,9H 2C,9HCheatgrass 0 5G 7H 7HWild Oats 0 2G 2C,3G 2C,5GWheat 0 0 7G 5GCorn 0 2G 6G 1C,6GBarley 0 5G 8G 4GSoybean 0 3C 3C,7H 2C,7HRice 5G 3C,7H 3C,7G 3C,8HSorghum 4G 2C,7H 2C,9H 3C,9HSugar beet 0 4C,8G 4C 3CCotton 0 0 2C,4G 3G______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 57 58 59 60Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 10C 2C,7G 10C 10CCocklebur 10C 10C 10C 10CVelvetleaf 9C 9C 9C 10CNutsedge 4C,9G 9G 9G 4C,9GCrabgrass 0 3G 5G 4GGiant Foxtail 5G 5G 7G 3C,6GBarnyardgrass 2C,6G 2C,6H 5C,9H 5C,9HCheatgrass 6G 2C,6G 2C,7G 9GWild Oats 1C 0 0 3C,5GWheat 2G 0 2G 6GCorn 5G 3C,7G 3C,7H 2U,9GBarley 4G 3G 5G 9GSoybean 0 4C,9G 5C,9G 9CRice 5G 7G 9G 4C,9GSorghum 3C,9G 3C,8H 3C,9G 4C,9GSugar beet 5C,9G 4C,9G 9C 9CCotton 10C 10C 9C 10CPREEMERGENCEMorningglory 3G 6H 6G 5GCocklebur 8H 2C,2H 5H 7HVelvetleaf 5G 6G 7G 7GNutsedge 0 10E 7G 5GCrabgrass 2G 3G 5G 2GGiant Foxtail 2G 5G 6G 0Barnyardgrass 7G 5G 3C,8H 9HCheatgrass 3G 3G 5G 8GWild Oats 0 2G 2G 2GWheat 0 2G 3G 7GCorn 2G 3G 2C,6G 3C,8HBarley 0 5G 5G 2C,8GSoybean 0 2C,5G 3C,4H 7HRice 5G 4C,8H 5C,9H 8HSorghum 3C,6G 3C,5G 4C,8G 3C,9HSugar beet 8G 9G 9G 6HCotton 0 3G 2G 0______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 61 62 63 64Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 10C 10C 10C 10CCocklebur 10C 10C 10C 10CVelvetleaf 10C 9C 3C,8G 3C,9GNutsedge 4C,9G 3C,9G 3G 2C,8GCrabgrass 3G 5G 2G 0Giant Foxtail 3C,8G 3C,8G 4G 4GBarnyardgrass 9C 9C 4C,9H 3C,8GCheatgrass 4C,9G 3C,9G 2C,4G 2C,5GWild Oats 2C,7G 5C,9G 2G 2C,7GWheat 3C,9G 3C,9G 4G 2GCorn 9C 2U,9G 3C,7H 2C,7GBarley 9H 9H 3C,6G 4GSoybean 9C 9C 3C,3H 4C,9GRice 5C,9G 5C,9G 9G 2C,8GSorghum 5C,9G 4C,9G 4C,9G 3C,9HSugar beet 9C 9C 4C,8H 9CCotton 10C 10C 4C,9G 3C,8GPREEMERGENCEMorningglory 4C,8G 5H 8G 2C,8GCocklebur 7H 6H 2C,4H 3C,7HVelvetleaf 7H 3C,8H 7G 5GNutsedge 8G 8G 5G 8GCrabgrass 3G 0 0 0Giant Foxtail 6G 5G 4G 0Barnyard grass 9H 7G 8H 7HCheatgrass 5C,9G 8G 5G 2GWild Oats 4C,8G 3C,8H 2G 2C,3GWheat 4C,9H 9G 3G 0Corn 3C,9H 3C,9H 3C,4G 2C,5GBarley 9G 8G 0 0Soybean 4C,7H 7G 0 3C,7HRice 5C,9H 9H 7H 9HSorghum 9H 9H 9H 3C,8HSugar beet 9C 3C,7G 8G 3C,8GCotton 3C,8H 2C,7G 9G 2C,5G______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 65 66 67 68Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 10C 2C,5G 2C,6G 2HCocklebur 10C 3C,9H 3C,9H 3HVelvetleaf 9C 2C,9G 2C,5H 1HNutsedge 2C,8G 3C,9G 2C,5G 4GCrabgrass 0 5G 0 0Giant Foxtail 2C,7G 2C,6G 2C,6G 2GBarnyardgrass 3C,9G 3C,9H 9H 7HCheatgrass 8G 4G 6G 0Wild Oats 2C,9G 5G 2C,7G 0Wheat 3G 2G 5G 0Corn 3C,9H 3C,9H 2C,9H 0Barley 2C,6G 8G 7G 0Soybean 5C,9G 5H 3C,7H 1HRice 5C,9G 2C,7G 3C,7G 2GSorghum 9G 3C,6G 3C,8H 5GSugar beet 9C 2C,7G 3C,8H 3GCotton 9C 7G 3C,8G 0PREEMERGENCEMorningglory 2C,8G 0 0 0Cocklebur 6H 2H 0 --Velvetleaf 4G 0 0 0Nutsedge 2C,8G 0 0 0Crabgrass 0 0 5G 0Giant Foxtail 0 0 5G 0Barnyardgrass 7H 0 7G 9HCheatgrass 6H 0 2G 0Wild Oats 3C,8G 0 2G 0Wheat 0 0 2G 0Corn 3C,6G 2G 2C,7G 2GBarley 2G 0 7G 4GSoybean 4C,8H 0 1H 0Rice 10H 4G 3G 4GSorghum 9H 5G 3C,7G 4GSugar beet 3C,9G 3G 8G 0Cotton 2C,8G 0 2G 0______________________________________ Cmpd. Cmpd. Cmpd. Cmpd. 69 70 71 72Rate kg/ha 0.05 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 1H 2C,4G 4C,9H 10CCocklebur 2C,7H 5H 3C,9H 10CVelvetleaf 5H 2C,5G 9C 10CNutsedge 0 0 2C,8G 5C,9GCrabgrass 0 0 5G 7GGiant Foxtail 2G 2G 6G 9CBarnyardgrass 0 6H 2C,7G 9CCheatgrass 2G 0 0 9CWild Oats 2G 2C,3G 2C,8G 3C,8GWheat 4G 0 6G 2C,9GCorn 2C,5G 3C,9H 3C,9H 4U,9GBarley 3G 0 3C,8G 3C,9GSoybean 3C,7H 2C,3H 4C,9H 9CRice 3C,9G 8G 2C,6G 9CSorghum 3C,9H 3C,9H 2C,9H 9CSugar beet 3C,6G 3C,7H 2C,6G 10CCotton 4G 2C 2C,8G 10CPREEMERGENCEMorningglory 3G 0 2G 9GCocklebur -- 0 5H 6HVelvetleaf 3G 0 0 2C,8GNutsedge 0 3G 0 9GCrabgrass 0 3G 7H 0Giant Foxtail 10H -- 5H 5GBarnyardgrass 0 3G 2C,6H 8HCheatgrass 0 3G 2C,6H 8GWild Oats 0 4G 0 8GWheat 0 0 2G 8GCorn 0 3G 2C,6H 9GBarley 3G 4G 0 8GSoybean 0 0 0 7HRice 0 5G 3C,7G 3C,9HSorghum 0 6G 2C,9H 9GSugar beet 2G 5G 6G 7GCotton 4G 5G 0 7G______________________________________ Cmpd. 73 Cmpd. 74 Cmpd. 75Rate kg/ha 0.05 0.05 0.05______________________________________POSTEMERGENCEMorningglory 10C 9C 10CCocklebur 10C 10C 10CVelvetleaf 10C 10C 10CNutsedge 9C 9C 6C,9GCrabgrass 0 3C,8H 0Giant Foxtail 6C,9G 6C,9H 5C,9GBarnyardgrass 9C 9C 9CCheatgrass 9C 9C 3C,9GWild Oats 5C,9G 9C 2C,5GWheat 9G 9G 3GCorn 2U,9G 9G 3C,9HBarley 4C,9G 4C,9G 4C,9HSoybean 9C 9C 5C,9GRice 9C 9C 5C,9GSorghum 5C,9G 9C 9CSugar beet 10C 10C 9CCotton 10C 9C 10CPREEMERGENCEMorningglory 9G 9G 8GCocklebur -- 9H 3C,5HVelvetleaf 9C 5C,9G 5HNutsedge 10E 10E 9GCrabgrass 3G 2G 0Giant Foxtail 3C,9H 7G 3C,6GBarnyardgrass 9H 9H 9HCheatgrass 9H 9H 9HWild Oats 3C,9G 2C,9H 3C,6GWheat 3C,9G 3C,9H 5GCorn 3C,9H 3C,9G 3C,9HBarley 9G 9G 7GSoybean 9H 9H 7HRice 9H 10E 9HSorghum 9H 10E 3C,9HSugar beet 4C,9G 9G 8GCotton 9G 9G 9G______________________________________ Cmpd. 76 Cmpd. 77Rate kg/ha 0.05 0.05______________________________________POSTEMERGENCEMorningglory 10C 10CCocklebur 10C 10CVelvetleaf 10C 10CNutsedge 2C,8G 9GCrabgrass 3G 6GGiant Foxtail 4C,9G 4C,9GBarnyardgrass 9H 9CCheatgrass 9C 5C,9GWild Oats 9C 9CWheat 4C,9G 4C,9GCorn 2C,8H 3U,9GBarley 4C,9G 3C,9GSoybean 9C 9CRice 9C 9CSorghum 4C,9G 5C,9GSugar beet 10C 9CCotton 4C,9G 10CPREEMERGENCEMorningglory 9G 9GCocklebur 9H 9HVelvetleaf 4C,8H 4C,8HNutsedge 5G 4GCrabgrass 0 0Giant Foxtail 5G 5GBarnyardgrass 8H 8HCheatgrass 9H 9HWild Oats 3C,9G 4C,9GWheat 9H 4C,9HCorn 7G 2C,9GBarley 9G 9GSoybean 3C,8H 9HRice 10E 10ESorghum 9H 10HSugar beet 4C,8G 9GCotton 9G 9G______________________________________
Claims
  • 1. A compound of the formula: ##STR59## wherein E is CH.sub.2 or a single bond;
  • W is O;
  • R is H or CH.sub.3 ;
  • R.sub.1 is F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, OCH.sub.2 CH.sub.2 OCH.sub.3, C.sub.1 -C.sub.4 haloalkoxy, C.sub.3 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, CO.sub.2 R.sub.3, CONR.sub.4 R.sub.5, SO.sub.4 NR.sub.4 R.sub.5, SO.sub.2 (OCH.sub.3)CH.sub.3, S(O).sub.n R.sub.6, OSO.sub.2 R.sub.7, C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, OH or C.sub.1 -C.sub.2 alkylthio, CH.sub.2 CN, C.sub.6 H.sub.5, ##STR60## R.sub.2 is CH(R.sub.16)CN, CH(R.sub.17)SCN, ##STR61## R.sub.3 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, ##STR62## CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 F, or C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or SCH.sub.3 ;
  • R.sub.4 is C.sub.1 -C.sub.3 alkyl;
  • R.sub.5 is H or C.sub.1 -C.sub.3 alkyl;
  • R.sub.4 and R.sub.5 may be taken together to form (CH.sub.2).sub.3 or (CH.sub.2).sub.4 ;
  • R.sub.6 is C.sub.1 -C.sub.3 alkyl, CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 C.tbd.CH;
  • R.sub.7 is C.sub.1 -C.sub.3 alkyl or N(CH.sub.3).sub.2 ;
  • R.sub.8 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 F, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or SCH.sub.3 or C.sub.3 -C.sub.6 cycloalkyl;
  • R.sub.9 is C.sub.1 -C.sub.2 alkyl;
  • R.sub.10 and R.sub.11 are independently C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, NHCH.sub.3 or N(CH.sub.3).sub.2 ;
  • R.sub.12 and R.sub.13 are independently H or C.sub.1 -C.sub.2 alkyl;
  • R.sub.14 is C.sub.1 -C.sub.3 alkyl;
  • R.sub.15 is H or CH.sub.3 ;
  • R.sub.16 is H, C.sub.1 -C.sub.2 alkyl or F;
  • R.sub.17 is H or C.sub.1 -C.sub.2 alkyl;
  • R.sub.18 is C.sub.1 -C.sub.2 alkyl;
  • R.sub.19 is H, Si(CH.sub.3).sub.3 or C.sub.1 -C.sub.2 alkyl;
  • R.sub.20 is H or C.sub.1 -C.sub.2 alkyl;
  • p is 1 or 2;
  • n is 0, 1, or 2;
  • A is ##STR63## X.sub.3 is CH.sub.3 or OCH.sub.3 ; and their agriculturally suitable salts; provided that
  • (1) when R.sub.2 is C(O)R.sub.17, then R.sub.1 is other than C.sub.1 -C.sub.4 haloalkyl or C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, OH or C.sub.1 -C.sub.2 alkylthio; and
  • (2) when R.sub.2 is C(O)R.sub.17 then R.sub.1 is other than SO.sub.2 NR.sub.4 R.sub.5 and SO.sub.2 N(OCH.sub.3)CH.sub.3.
  • 2. A compound of claim 1 wherein R is H.
  • 3. A compound of claim 2 where E is a single bond.
  • 4. A compound of claim 3 where
  • R.sub.2 is CH.sub.2 CN, CH.sub.2 N.sub.3, ##STR64##
  • 5. A compound of claim 4 wherein R.sub.1 is F, Cl, Br, NO.sub.2, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkyl substituted with 1-3 F or Cl or 1 Br, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkenyl substituted with 1-3 F or Cl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkoxy substituted with 1-3 F or Cl or 1-Br, allyloxy, propargyloxy, OC(Cl).dbd.CHCl, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, CO.sub.2 CH.sub.2 CH.dbd.CH.sub.2, CO.sub.2 CH.sub.2 CH.sub.2 Cl, CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3, CONH(C.sub.1 -C.sub.2 alkyl), CONCH.sub.3 (C.sub.1 -C.sub.2 alkyl, SO.sub.2 N(OCH.sub.3)CH.sub.3, SO.sub.2 NH(C.sub.1 -C.sub.2 alkyl), SO.sub.2 N(C.sub.1 -C.sub.2 alkyl).sub.2, S(O).sub.n C.sub.1 -C.sub.3 alkyl, OSO.sub.2 C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or SCH.sub.3, C.sub.6 H.sub.5 and R.sub.1 --A, R.sub.1 --B, R.sub.1 --C, R.sub.1 --D, R.sub.1 --E, R.sub.1 --F, R.sub.1 --G, R.sub.1 --H, R.sub.1 --I, R.sub.1 --J, R.sub.1 --K, R.sub.1 --L, R.sub.1 --M, R.sub.1 --N, R.sub.1 --O, R.sub.1 --P, R.sub.1 --Q R.sub.1 --R, R.sub.1 --S, R.sub.1 --t, R.sub.1 --U, R.sub.1 --V or R.sub.1 --W.
  • 6. A compound of claim 5 where
  • R.sub.1 is F, Cl, Br, NO.sub.2, CH.sub.3, CF.sub.3 C.sub.1 -C.sub.2 alkoxy, allyloxy, OC(Cl).dbd.CHCl, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, CO.sub.2 NHCH.sub.3, CO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 NHCH.sub.3 SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 CH.sub.3, SO.sub.2 C.sub.2 H.sub.5, OSO.sub.2 CH.sub.3, OSO.sub.2 C.sub.2 H.sub.5, R.sub.1 --A, R.sub.1 --B or R.sub.1 --C.
  • 7. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
  • 8. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
  • 9. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
  • 10. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
  • 11. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
  • 12. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.
  • 13. A method of controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 1.
  • 14. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 2.
  • 15. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 3.
  • 16. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 4.
  • 17. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 5.
  • 18. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 6.
RELATED APPLICATION

This is a division of application Ser. No. 108,646, filed Oct. 15, 1987, now U.S. Pat. No. 4,786,314, which, in turn, is a continuation-in-part of Ser. No. 041,790, filed Apr. 23, 1987, now abandoned, which is a division of 860,229, filed May 12, 1986, now U.S. Pat. No. 4,678,498, which, is a continuation-in-part of 743,955, filed June 12, 1985, now abandoned.

US Referenced Citations (5)
Number Name Date Kind
4310346 Levitt et al. Jan 1982
4312990 Haugvoitz Jan 1982
4348219 Levitt Sep 1982
4511392 Rorer Apr 1985
4600428 Szczepanski Jul 1986
Foreign Referenced Citations (5)
Number Date Country
EPA30139 Jun 1981 EPX
EPA112803 Dec 1982 EPX
EPA44209 Oct 1984 EPX
842722 Oct 1984 ZAX
845216 Dec 1984 ZAX
Non-Patent Literature Citations (3)
Entry
Arznetimittleforschung, 13 (1936) 269-280, Jacker et al.
Chemical Abstracts, 96: 6381d (1982), Yamanouchi.
Fujikura et al., Chem. Pharm. Bull. 30 (1982), 4092-41.
Divisions (2)
Number Date Country
Parent 108646 Oct 1987
Parent 860229 May 1986
Continuation in Parts (2)
Number Date Country
Parent 41790 Apr 1987
Parent 743955 Jun 1985