Claims
- 1. A compound of the formula ##STR67## wherein: J is ##STR68## W is O or S; R is H or CH.sub.3 ;
- R.sup.1 is H; CH.sub.3 ; CH.sub.2 OCH.sub.3 ; CH.sub.2 OC.sub.2 H.sub.5 ; CH.sub.2 CN; CH.sub.2 SCH.sub.3, CH.sub.2 SC.sub.2 H.sub.5 ; C.sub.2 -C.sub.6 alkyl optionally substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CN or one or more halogens; C.sub.3 -C.sub.4 alkenyl; C.sub.3 -C.sub.4 haloalkenyl; C.sub.3 -C.sub.6 cycloalkyl; C(O)R.sup.5 ; N(CH.sub.3).sub.2 ; or Q.sup.1 ;
- R.sup.2 is C.sub.1 -C.sub.4 alkyl optionally substituted with one CN, C.sub.2 -C.sub.3 alkylcarbonyl, methoxycarbonyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfonyl, S(O).sub.2 NR.sup.6 R.sup.7, OH or one or more halogens; C.sub.2 -C.sub.4 alkenyl optionally substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CN or one or more halogens; CN; C(O)R.sup.8 ; C(O)OR.sup.9 ; C(O)NR.sup.10 R.sup.11 ; C(R.sup.12).dbd.NOR.sup.13 ; C(R.sup.14)(OR.sup.15)(OR.sup.16); S(O).sub.n R.sup.17 ; S(O).sub.2 NR.sup.18 R.sup.19 ; NO.sub.2 ; halogen; or OR.sup.73 ;
- R.sup.3 is H, halogen or C.sub.1 -C.sub.4 alkyl;
- R.sup.4 is H, C.sub.1 -C.sub.4 alkyl optionally substituted with one CN, C.sub.2 -C.sub.3 alkylcarbonyl, methoxycarbonyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfonyl, S(O).sub.2 NR.sup.6 R.sup.7, OH or one or more halogens; C.sub.2 -C.sub.4 alkenyl optionally substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CN or one or more halogens; CN; C(O)R.sup.8 ; C(O)OR.sup.9 ; C(O)NR.sup.10 R.sup.11 ; C(R.sup.12).dbd.NOR.sup.13 ; S(O).sub.n R.sup.17 ; S(O).sub.2 NR.sup.18 R.sup.19 ; or halogen;
- R.sup.5 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or NR.sup.20 R.sup.21 ;
- R.sup.6 is H, C.sub.1 -C.sub.2 alkyl or OCH.sub.3 ;
- R.sup.7 is C.sub.1 -C.sub.2 alkyl; or
- R.sup.6 and R.sup.7 can be taken together as --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --;
- R.sup.8 is H, C.sub.1 -C.sub.3 alkyl or cyclopropyl;
- R.sup.9 is CH.sub.3 ; C.sub.2 -C.sub.3 alkyl optionally substituted with one C.sub.1 -C.sub.2 alkoxy, OH, CN or one or more halogens; C.sub.3 -C.sub.4 alkenyl; or propargyl;
- R.sup.10 is H, C.sub.1 -C.sub.3 alkyl or OCH.sub.3 ;
- R.sup.11 is C.sub.1 -C.sub.3 alkyl; or
- R.sup.10 and R.sup.11 can be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --;
- R.sup.12 is H, C.sub.1 -C.sub.3 alkyl, allyl, halogen, CN, N.sub.3, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio or SCN;
- R.sup.13 is C.sub.1 -C.sub.3 alkyl or allyl;
- R.sup.14 is H or C.sub.1 -C.sub.3 alkyl;
- R.sup.15 and R.sup.16 are independently C.sub.1 -C.sub.2 alkyl;
- R.sup.17 is C.sub.1 -C.sub.4 alkyl, optionally substituted with one C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, CN or one or more halogens; C.sub.3 -C.sub.4 alkenyl; or cyclopropylmethyl;
- R.sup.18 is H, C.sub.1 -C.sub.3 alkyl or OCH.sub.3 ;
- R.sup.19 is H or C.sub.1 -C.sub.2 alkyl; or
- R.sup.18 and R.sup.19 can be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --;
- R.sup.20 and R.sup.21 are independently C.sub.1 -C.sub.2 alkyl; or
- R.sup.20 and R.sup.21 can be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --;
- R.sup.71 is H, halogen or CF.sub.3 ;
- R.sup.73 is C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogens, CN, C.sub.1 -C.sub.2 alkoxy, or C.sub.1 -C.sub.2 alkylthio; C(O)R.sup.74 ; SO.sub.2 R.sup.75 ; C.sub.3 -C.sub.4 alkenyl; or propargyl;
- R.sup.74 is C.sub.1 -C.sub.4 alkyl optionally substituted with C.sub.1 -C.sub.2 alkoxy, one or more halogens, or CN; C.sub.3 -C.sub.4 alkenyl; or C.sub.1 -C.sub.3 alkoxy;
- R.sup.75 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ;
- n is 0, 1 or 2;
- Q.sup.1 is ##STR69## A is ##STR70## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, 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 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, ##STR71## or N(OCH.sub.3)CH.sub.3 ; p is 2 or 3;
- Q.sup.3 and Q.sup.4 are independently O or S;
- R.sup.22 is H or C.sub.1 -C.sub.3 alkyl;
- R.sup.23 and R.sup.24 are independently C.sub.1 -C.sub.3 alkyl;
- Z is N; and
- X.sup.3 is CH.sub.3 or OCH.sub.3 ;
- q is 0 or 1;
- R.sup.25 and R.sup.26 are independently H, CH.sub.3 or Cl;
- R.sup.27 and R.sup.28 are independently H, F, or CH.sub.3 ;
- R.sup.29 is H, CH.sub.3 or OCH.sub.3 ;
- R.sup.30 is H or CH.sub.3 ;
- R.sup.31, R.sup.32 and R.sup.33 are independently H, CH.sub.3 or OCH.sub.3 ;
- R.sup.34, R.sup.35 and R.sup.36 are independently H, CH.sub.3, CH.sub.2 CH.sub.3, Cl, Br, OCH.sub.3 or OCH.sub.2 CH.sub.3 ;
- R.sup.37 is H or C.sub.1 -C.sub.2 alkyl;
- R.sup.38 is CH.sub.3 ;
- R.sup.39 is H, C.sub.1 -C.sub.2 alkyl, OCH.sub.3 or SCH.sub.3 ;
- R.sup.40 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ;
- R.sup.41 and R.sup.42 are independently H, or CH.sub.3 ;
- R.sup.43 is H, CH.sub.3, CH.sub.2 CH.sub.3 or C.sub.3 H.sub.7 ;
- W.sup.1 is O or S;
- W.sup.2 is O, S or NR.sup.44 ;
- R.sup.44 is H or CH.sub.3 ;
- and their agriculturally suitable salts; provided that:
- (a) when W is S, then R is H, A is A-1 and Y is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.3, 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 ##STR72## (b) when the total number of carbon atoms of X and Y is greater than four, then the number of carbons of Q.sup.1 is less than or equal to eight;
- (c) when A is A-6 then R is H;
- (d) when J is J-1, A is A-1 and X and/or Y is alkyl, then R.sup.2 is other than CN or NO.sub.2.
- 2. A compound of claim 1 wherein:
- W is O;
- R.sup.1 is H, C.sub.1 -C.sub.6 alkyl, allyl, CH.sub.2 OCH.sub.3, CH.sub.2 OC.sub.2 H.sub.5, CH.sub.2 SCH.sub.3 phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, C(O)OCH.sub.3 or C(O)N(CH.sub.3).sub.2 ;
- X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, F, Cl, Br, I, CH.sub.2 F, 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, C(O)R.sup.22, ##STR73## cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3.
- 3. A compound of claim 2 wherein:
- R.sup.3 is H, CH.sub.3, Cl or Br; and
- R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)NR.sup.10 R.sup.11, C(R.sup.12).dbd.NOR.sup.13, C(R.sup.14)(OR.sup.15)(OR.sup.16), S(O).sub.n R.sup.17, S(O).sub.2 NR.sup.18 R.sup.19, F, Cl or Br;
- R.sup.8 is H or C.sub.1 -C.sub.2 alkyl;
- R.sup.9 is C.sub.1 -C.sub.2 alkyl or CH.sub.2 CH.sub.2 Cl;
- R.sup.10 is H or CH.sub.3 ;
- R.sup.11 is CH.sub.3 ;
- R.sup.12 is H, CH.sub.3, C.sub.2 H.sub.5 or Cl;
- R.sup.13 is CH.sub.3 ;
- R.sup.14 is H or C.sub.1 -C.sub.2 alkyl;
- R.sup.15 and R.sup.16 are CH.sub.3 ;
- R.sup.17 is C.sub.1 -C.sub.2 alkyl;
- R.sup.18 is H or CH.sub.3 ;
- R.sup.19 is CH.sub.3 ; and
- n is 0 or 2.
- 4. A compound of claim 3 wherein:
- R.sup.2 is C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)NR.sup.10 R.sup.11, C(R.sup.12).dbd.NOR.sup.13, C(R.sup.14)(OR.sup.15)(OR.sup.16), S(O).sub.n R.sup.17, S(O).sub.2 NR.sup.18 R.sup.19, F, Cl, Br, or OR.sup.73.
- 5. A compound of claim 4 wherein:
- R is H; and
- R.sup.71 is H.
- 6. A compound of claim 5 wherein:
- J is J-1.
- 7. A compound of claim 5 wherein:
- J is J-2.
- 8. A compound of claim 5 wherein:
- J is J-3.
- 9. A compound of claim 6 wherein:
- R.sup.2 is C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH2SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3, S(O).sub.2 C.sub.2 H.sub.5, S(O).sub.2 N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkoxy, OC(O)CH.sub.3, or OSO.sub.2 CH.sub.3 ;
- R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3, S(O).sub.2 C.sub.2 H.sub.5 or S(O).sub.2 N(CH.sub.3).sub.2 ;
- R.sup.8 is C.sub.1 -C.sub.2 alkyl;
- R.sup.9 is C.sub.1 -C.sub.2 alkyl.
- 10. A compound of claim 7 wherein:
- R.sup.2 is C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3, S(O).sub.2 C.sub.2 H.sub.5, S(O).sub.2 N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkoxy, OC(O)CH.sub.3, or OSO.sub.2 CH.sub.3 ;
- R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, Q.sup.2, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3 or S(O).sub.2 N(CH.sub.3).sub.2 ;
- R.sup.8 is C.sub.1 -C.sub.2 alkyl;
- R.sup.9 is C.sub.1 -C.sub.2 alkyl.
- 11. A compound of claim 8 wherein:
- R.sup.2 is C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3, S(O).sub.2 C.sub.2 H.sub.5, S(O).sub.2 N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkoxy, OC(O)CH.sub.3, or OSO.sub.2 CH.sub.3 ;
- R.sup.4 is H, C.sub.1 -C.sub.2 alkyl, CH.sub.2 CN, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 S(O).sub.2 CH.sub.3, C(O)R.sup.8, C(O)OR.sup.9, C(O)N(CH.sub.3).sub.2, S(O).sub.2 CH.sub.3 or S(O).sub.2 N(CH.sub.3).sub.2 ;
- R.sup.8 is C.sub.1 -C.sub.2 alkyl;
- R.sup.9 is C.sub.1 -C.sub.2 alkyl.
- 12. A compound of claim 9 wherein:
- A is A-1;
- X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, or Cl; and
- Y is CH.sub.3, OCH.sub.3, NHCH.sub.3 or N(CH.sub.3).sub.2.
- 13. A compound of claim 10 wherein:
- A is A-1;
- X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, or Cl; and
- Y is CH.sub.3, OCH.sub.3, NHCH.sub.3 or N(CH.sub.3).sub.2.
- 14. A compound of claim 11 wherein:
- A is A-1;
- X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, or Cl; and
- Y is CH.sub.3, OCH.sub.3, NHCH.sub.3 or N (CH.sub.3).sub.2.
- 15. The compound of claim 1 which is: (1-methylethyl)2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-1-methyl-1H-pyrrole-3-carboxylate.
- 16. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising a herbicidally effective amount of a compound in any of claims 1, 2, 3, 4 or 5 and at least one of the following surfactants: solid diluent or liquid diluent.
- 17. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected a herbicidally effective amount of a compound in any of claims 1, 2, 3, 4 or 5.
CROSS-REFERENCE TO RELATED APPLICATION
This application is a continuation-in-part of U.S. Ser. No. 07/573,074 filed Aug. 29, 1990, now abandoned.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/US91/05822 |
8/22/1991 |
|
|
2/24/1993 |
2/24/1993 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO92/04319 |
3/19/1992 |
|
|
US Referenced Citations (8)
Foreign Referenced Citations (2)
Number |
Date |
Country |
0126711 |
Nov 1984 |
EPX |
0161211 |
Nov 1985 |
EPX |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
573074 |
Aug 1990 |
|