Claims
- 1. A compound of the formula: ##STR59## 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, ##STR60## R.sub.2 is ##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; ##STR63## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -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.2 -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, ##STR64## or N(OCH.sub.3)CH.sub.3); 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; and Z is, N;
- and their agriculturally suitable salts;
- provided that
- (1) when W is S, then R is H, 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 ##STR65## (2) 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;
- (3) 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;
- (4) 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 ; and
- (5) 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 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, 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, ##STR66## SCF.sub.2 H, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3.
- 4. A compound of claim 3 where
- R.sub.2 is CH.sub.2 CN, CH.sub.2 N.sub.3, ##STR67##
- 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 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 114 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. --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, 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-methoxy-6-methyl-1,3,5-triazin-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 6 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 7 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 8 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 application is a continuation-in-part of copending application U.S. Ser. No. 041,790, filed Apr. 23, 1987, now abandoned, which is a divisional of copending application U.S. Ser. No. 860,229, filed May 12, 1986, now U.S. Pat. No. 4,678,498, which is a continuation-in-part application of U.S. Ser. No. 743,955, filed June 12, 1985, now abandoned.
US Referenced Citations (6)
Foreign Referenced Citations (5)
Number |
Date |
Country |
30139 |
Jun 1981 |
EPX |
112803 |
Jul 1984 |
EPX |
44209 |
Oct 1984 |
EPX |
842722 |
Oct 1984 |
ZAX |
845216 |
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Non-Patent Literature Citations (3)
Entry |
Jucker et al., Arznetimittleforschung, 13 (1936) 269-280. |
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Divisions (1)
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Number |
Date |
Country |
Parent |
860229 |
May 1986 |
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Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
41790 |
Apr 1987 |
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Parent |
743955 |
Jun 1985 |
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