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US 5,472,933 AGranted
Herbicidal pyrrolesulfonylureas
AssigneeE. I. Du Pont de Nemours and Company
InventorsWilliam T. Zimmerman, Bruce A. Lockett, John Cuomo
Life of this patent
Estimating the term…
Abstract
This invention relates to certain herbicidal pyrrolesulfonylureas, compositions thereof and a method for their use as herbicides or plant growth regulants.
Claims17
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.
105 more elements
Dependencies are inferred from the claim text.