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US 4,981,509 AGranted
Herbicidal sulfonamides
AssigneeE. I. Du Pont de Nemours and Company
InventorCraig L. Hillemann
Life of this patent
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Abstract
This invention relates to certain sulfonylurea herbicidal compounds, agriculturally suitable compositions thereof and a method of their use.
Claims43
A compound of the structural formula:
- ##STR44## wherein R is H or CH.sub.3 ;
- R.sub.1 is C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.4 -C.sub.6 cycloalkylalkyl or C.sub.4 -C.sub.5 cycloalkyl;
- R.sub.2 is C.sub.2 -C.sub.6 alkoxy, C.sub.3 -C.sub.6 cycloalkoxy, C.sub.4 -C.sub.6 cycloalkylalkoxy, OCF.sub.2 H, C.sub.2 -C.sub.6 haloalkoxy, C.sub.2 -C.sub.6 alkenyloxy, C.sub.2 -C.sub.6 haloalkenyloxy, C.sub.3 -C.sub.6 alkynyloxy, C.sub.3 -C.sub.6 haloalkynyloxy, C.sub.2 -C.sub.4 alkoxyalkoxy, C.sub.2 -C.sub.4 haloalkoxyalkoxy, C.sub.2 -C.sub.4 alkylthioalkoxy, C.sub.2 C.sub.4 haloalkylthioalkoxy, C.sub.2 -C.sub.4 alkylsulfinylalkoxy, C.sub.2 -C.sub.4 haloalkylsulfinylalkoxy, C.sub.2 -C.sub.4 alkylsulfonylalkoxy, C.sub.2 -C.sub.4 haloalkylsulfonylalkoxy, C.sub.2 -C.sub.4 cyanoalkoxy, OCH.sub.2 C(O)CH.sub.3, OCH.sub.2 CH.sub.2 C(O)CH.sub.3, C.sub.2 -C.sub.4 aminoalkoxy, C.sub.2 -C.sub.8 alkylthio, C.sub.3 -C.sub.6 cycloalkylthio, C.sub.4 -C.sub.6 cycloalkylalkythio, SCF.sub.2 H, C.sub.2 -C.sub.8 haloalkylthio, C.sub.2 -C.sub.6 alkenylthio, C.sub.2 -C.sub.6 haloalkenylthio, C.sub.3 -C.sub.6 alkynylthio, C.sub.3 - C.sub.6 haloalkynylthio, C.sub.2 -C.sub.4 alkoxyalkylthio, C.sub.2 -C.sub.4 haloalkoxyalkylthio, C.sub.2 -C.sub.4 alkylthioalkylthio, C.sub.2 -C.sub.4 haloalkythioalkylthio, C.sub.2 -C.sub.4 cyanoalkylthio, SCH.sub.2 C(O)CH.sub.3, SCH.sub.2 CH.sub.2 C(O)CH.sub.3, C.sub.2 -C.sub.4 aminoalkylthio, SC.sub.6 H.sub.5, SCH.sub.2 C.sub.6 H.sub.5, C.sub.1 -C.sub.8 alkylsulfinyl, C.sub.3 -C.sub.6 cycloalkylsulfinyl, sulfinyl, C.sub.4 -C.sub.6 cycloalkylalkylsulfinyl, C.sub.1 -C.sub.8 haloalkylsulfinyl, C.sub.2 -C.sub.6 alkenylsulfinyl, C.sub.2 -C.sub.6 haloalkenylsulfinyl, C.sub.3 -C.sub.6 alkynylsulfinyl, C.sub.3 -C.sub.6 haloalkynylsulfinyl, C.sub.2 -C.sub.4 alkoxyalkylsulfinyl, C.sub.2 -C.sub.4 haloalkoxyalkylsulfinyl, C.sub.2 -C.sub.4 cyanoalkylsulfinyl, S(O)CH.sub.2 C(O)CH.sub.3, S(O)CH.sub.2 CH.sub.2 C(O)CH.sub.3, C.sub.2 -C.sub.4 aminoalkylsulfinyl, C.sub.3 -C.sub.6 cycloalkylsulfonyl, C.sub.4 C.sub.6 cycloalkylalkylsulfonyl, C.sub.1 -C.sub.8 haloalkylsulfonyl, C.sub.2 -C.sub.6 alkenylsulfonyl, C.sub.2 C.sub.6 haloalkenylsulfonyl, C.sub.3 -C.sub.6 alkynylsulfonyl, C.sub.3 -C.sub.6 haloalkynylsulfonyl, C.sub.2 -C.sub.4 alkoxyalklsulfonyl, C.sub.2 -C.sub.4 haloalkoxyalkylsulfonyl, C.sub.2 -C.sub.4 cyanoalkylsulfonyl, SO.sub.2 CH.sub.2 C(O)CH.sub.3, SO.sub.2 CH.sub.2 CH.sub.2 C(O)CH.sub.3, C.sub.2 -C.sub.4 aminoalkylsulfonyl, CH.sub.2 F, CH.sub.2, CH.sub.2 Cl, CHCl.sub.2, CH.sub.2 Br, CHBr.sub.2, C.sub.2 -C.sub.6 substituted with 1-3 atoms of F, Cl or Br, C.sub.2 - C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 haloalkynyl, OC(O)C.sub.1 -C.sub.4 alkyl, CH.sub.2 C(O)NR.sub.a R.sub.b, NHC.sub.3, NR.sub.b R.sub.c or C.sub.1 -C.sub.4 alkyl substituted with C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.4 cycloalkoxy, cyclopropylmethoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 haloalkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.3 -C.sub.4 haloalkynyloxy, C.sub.2 -C.sub.4 alkoxyalkoxy, C.sub.2 -C.sub.4 aminoalkoxy, C.sub.1 -C.sub.4 alkylcarbonyloxy, C.sub.1 -C.sub.4 haloalkylcarbonyloxy, C.sub.1 -C.sub.4 carbamoyloxy, C.sub.1 C.sub.4 alkoxycarbonyloxy, OH, OP(O)(OC.sub.1 -C.sub.2 alkyl).sub.2, C.sub.1 -C.sub.4 alkylsulfonyloxy, C.sub.1 -C.sub.2 haloalkylsulfonyloxy, OSi(CH.sub.3).sub.3, OSi(CH.sub.3).sub.2 C(CH.sub.3).sub.3, C.sub.1 -C.sub.4 alkylthio, C.sub.3 -C.sub.4 cycloalkylthio, cyclopropylmethylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.4 alkenylthio, C.sub.2 -C.sub.4 haloalkenylthio, C.sub.3 -C.sub.4 alkynylthio, C.sub.3 -C.sub.4 haloalkynylthio, C.sub.2 -C.sub.4 alkoxyalkylthio, C.sub.2 -C.sub.4 aminoalkylthio, SH, SP(O)(OC.sub.1 -C.sub.2 alkyl).sub.2, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.3 -C.sub.4 cycloalkylsulfonyl, cyclopropylmethylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.2 -C.sub.4 alkenylsulfinyl, C.sub.2 -C.sub.4 haloalkenylsulfinyl, C.sub.3 -C.sub.4 alkynylsulfinyl, C.sub.3 -C.sub.4 haloalkynylsulfinyl, C.sub.2 -C.sub.4 alkoxyalkylsulfinyl, C.sub.2 -C.sub.4 aminoalkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.3 -C.sub.4 cycloalkylsulfonyl, cyclopropylmethylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, C.sub.2 -C.sub.4 alkenylsulfonyl, C.sub.2 -C.sub.4 haloalkenylsulfonyl, C.sub.3 -C.sub.4 alkynylsulfonyl, C.sub.3 -C.sub.4 haloalkynylsulfonyl, C.sub.2 -C.sub.4 alkoxyalkylsulfonyl or C.sub.2 -C.sub.4 aminoalkylsulfonyl;
- R.sub.a and R.sub.b are independently H or C.sub.1 -C.sub.3 alkyl;
- R.sub.c is C.sub.2 -C.sub.4 alkyl or cyclopropylmethyl;
- X is CH.sub.3, or OC.sub.2 H.sub.5 ;
- Y is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, NHCH.sub.3 or N(CH.sub.3).sub.2 ;
- and
- Z is N;
- and
- their agriculturally suitable salts;
- provided that
- (1) when R.sub.2 is OCH.sub.2 CF.sub.3 and R.sub.1 is CH.sub.3 or CH.sub.2 CH.sub.3, then X and Y cannot simultaneously be OCH.sub.3.
10 more elements
Dependencies are inferred from the claim text.