Claims
- 1. A compound of the formula: ##STR56## 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, ##STR57## R.sub.2 is ##STR58## 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, ##STR59## 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 and 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 ##STR60## 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, ##STR61## 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, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr;
- 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, Z is CH 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, ##STR62## (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 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.
- 2. A compound of claim 1 where
- W is O; and
- R is H.
- 3. A compound of claim 2 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.2 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, ##STR63## OCF.sub.2 H, SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3 ; Z is CH.
- 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 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 subsituted with 1-3F of Cl or 1Br, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkenyl substituted with 1-3F or Cl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkoxy subsituted with 1-3F 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
- 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. A compound of claim 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.
- 8. The compound of claim 1 which is 4-(cyanomethyl)-2-[[4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester.
- 9. 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.
- 10. 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.
- 11. 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.
- 12. 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.
- 13. 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.
- 14. 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.
- 15. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.
- 16. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 8 and at least one of the following: surfactant, solid or liquid diluent.
- 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 1.
- 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 2.
- 19. 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.
- 20. 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.
- 21. 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.
- 22. 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.
- 23. 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 7.
- 24. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim 8.
RELATED APPLICATION
This is a continuation-in-part of application U.S. Ser. No. 743,955 filed June 12, 1985, now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4511392 |
Rorer |
Apr 1985 |
|
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
743955 |
Jun 1985 |
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