Herbicidal heterocyclic sulfonamides
AssigneeE. I. Du Pont de Nemours and Company
InventorBarry A. Wexler
Life of this patent
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Abstract
This invention relates to certain heterocyclic sulfonylurea herbicidal compounds, agriculturally suitable compositions thereof and a method of their use.
Claims42
A compound of Formula I ##STR49## wherein J is ##STR50## R is H, C.sub.1 -C.sub.3 alkyl, phenyl, SO.sub.2 NR.sub.a R.sub.b, C.sub.1 -C.sub.2 haloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.2 -C.sub.4 alkylthioalkyl, C.sub.2 -C.sub.4 alkylsulfinylalkyl, C.sub.2 -C.sub.4 alkylsulfonylalkyl, CO.sub.2 C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.4 alkylcarbonyl, C.sub.1 -C.sub.2 alkylsulfonyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl or C.sub.1 -C.sub.2 alkyl substituted with CO.sub.2 C.sub.1 -C.sub.2 alkyl;
- R.sub.1 is H or CH.sub.3 ;
- R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sub.c R.sub.d, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CN, CO.sub.2 R.sub.e, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkylthio, amino, C.sub.1 -C.sub.2 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio, CN, OH or SH;
- R.sub.a and R.sub.b are independently C.sub.1 -C.sub.2 alkyl;
- R.sub.c is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy;
- R.sub.d is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl;
- or
- R.sub.c and R.sub.d may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;
- R.sub.e is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.1 -C.sub.2 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl;
- R' is C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 haloalkyl, C.sub.1 -C.sub.5 alkyl substituted with one or two R.sub.3 groups, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 haloalkenyl, C.sub.3 -C.sub.5 alkenyl substituted with one or two R.sub.3 groups, C.sub.3 -C.sub.5 alkynyl, C.sub.3 -C.sub.5 haloalkynyl, C.sub.3 -C.sub.5 alkynyl substituted with one or two R.sub.3 groups, C.sub.3 -C.sub.5 cycloalkyl, C.sub.3 -C.sub.5 halocycloalkyl, C.sub.3 -C.sub.5 cycloalkyl substituted with one or two R.sub.4 groups, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.4 -C.sub.7 halocycloalkylalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl substituted with one or two R.sub.4 groups, phenyl or benzyl;
- R.sub.3 is C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CN, NO.sub.2, OH, OR.sub.5 or di-(C.sub.1 -C.sub.3 alkyl)amino;
- R.sub.4 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, CN, NO.sub.2, OH, OR.sub.5 or di-(C.sub.1 -C.sub.3 alkyl)amino;
- R.sub.5 is SO.sub.2 CH.sub.3, Si(CH.sub.3).sub.3, C.sub.2 -C.sub.3 alkylcarbonyl or CO.sub.2 C.sub.1 -C.sub.2 alkyl;
- E is a single bond or CH.sub.2 ;
- W is O or S;
- n is O or 1;
- n' is 0 or 1;
- A is ##STR51## 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, di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.3 -C.sub.5 cycloalkyl;
- 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.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, azido, cyano, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, ##STR52## or N(OCH.sub.3)CH.sub.3 ;
- m is 2 or 3;
- L.sub.1 and L.sub.2 are independently O or S;
- R.sub.6 is H or C.sub.1 -C.sub.3 alkyl;
- R.sub.7 and R.sub.8 are independently C.sub.1 -C.sub.3 alkyl;
- and
- Z is CH;
- and their agriculturally suitable salts;
- provided that
- (a) when X is Cl, F, Br or I, then Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H;
- (b) when W is S, then R.sub.1 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.dbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or 1,3-dioxolan-2-yl;
- (c) when the total number of carbons of X and Y is greater than four, then the number of carbons of R must be less than or equal to two;
- (d) when J is J-1 or J-2, then R' is other than C.sub.3 -C.sub.5 cycloalkyl or phenyl;
- (e) when J is J-5, J-6 or J-7 wherein E is a single bond, then R' is other than C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, phenyl, benzyl, cyclopentyl or C.sub.4 -C.sub.7 cycloalkylalkyl;
- (f) when either or both of X and Y are OCF.sub.2 H then J is J-1, J-2, J-8, J-9, J-10 or J-11;
- and
- (g) when the total number of carbon atoms of X and Y is greater than four, then the total number of carbon atoms of R.sub.2 and R' must be less than or equal to 7,
- (h) when J is J-5, J-6 or J-7 and E is CH.sub.2, then R' is other than C.sub.1 -C.sub.5 alkyl.
Dependencies are inferred from the claim text.