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US 4,902,339 AGranted
Herbicidal sulfonamides
AssigneeE. I. Du Pont de Nemours and Company
InventorsJoel R. Christensen, Morris P. Rorer
Life of this patent
Estimating the term…
Abstract
The invention relates to certain sulfonylurea compounds having a carbocyclic or heterocyclic ring ortho to the sulfonylurea linkage, compositions thereof and a method of their use as herbicides or plant growth regulants.
Claims30
A compound of which is ##STR50## wherein J is ##STR51## W is O or S;
- R is H or CH.sub.3 ;
- E.sub.1 is O, S, SO, SO.sub.2 or a single bond.
- X.sub.a is CH.sub.2, CH(CH.sub.3), CH.sub.2 CH.sub.2, CH.sub.2 CH.sub.2 CH.sub.2 or CO;
- E is a single bond, CH.sub.2 or O;
- Q is selected from ##STR52## wherein Q-1 through Q-87 may be optionally substituted with 1 or 2 groups selected from C.sub.1 -C.sub.2 alkyl or C.sub.1 -C.sub.2 haloalkyl;
- R.sub.5 and R.sub.6 are independently H or C.sub.1 -C.sub.3 alkyl;
- X.sub.b is O or NR.sub.5 ;
- and
- X.sub.c is O, S, SO, SO.sub.2 or NR.sub.5.
- R.sub.1 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.a R.sub.b, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CH.sub.2 CN, CN, CO.sub.2 R.sub.c, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkylthio, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 alkylthioalkyl, CH.sub.2 N.sub.3 or NR.sub.d R.sub.e ;
- R.sub.a is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy;
- R.sub.b is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl;
- or
- R.sub.a and R.sub.b 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.c 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.2 -C.sub.3 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl;
- R.sub.d and R.sub.e are independently H or C.sub.1 -C.sub.2 alkyl;
- A is ##STR53## 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, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.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.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.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, ##STR54## 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.2 is H or C.sub.1 -C.sub.3 alkyl;
- R.sub.3 and R.sub.4 are independently C.sub.1 -C.sub.3 alkyl;
- Z is N, and;
- X.sub.3 is CH.sub.3 or OCH.sub.3 ;
- and their agriculturally suitable salts;
- provided that
- (a) when Q contains 2 heteroatoms selected from 0-2 oxygen and 0-2 sulfur, said heteroatoms are not bonded directly to one another unless in the form O--SO.sub.2, and when Q contains 3 nitrogen heteroatoms, only two of these may be bonded directly together;
- (b) when J is J-2 or J-3, the substituent E.sub.1 X.sub.a Q and the sulfonylurea bridge are on adjacent carbon atoms;
- (c) when E is O, then J is J-1 and W is O;
- (d) when W is S, then R is H, A is A-1, 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 1,3-dioxolan-2-yl;
- (e) when the total number of carbon atoms of X and Y is greater than four, then the number of carbons of R.sub.1 must be less than or equal to two, and the number of carbons of the substituent on Q must also be less than or equal to two;
- (f) when A is A-1 and J is J-1 wherein E is a single bond, X.sub.a is CH.sub.2, CH(CH.sub.3) or CH.sub.2 CH.sub.2 and Q is a 5-membered heterocyclic ring containing one endocyclic double bond or a 6-membered heterocyclic ring containing 1 or 2 endocyclic double bonds which is unsubstituted or substituted by one or more C.sub.1 -C.sub.4 alkyl groups then said heterocycle must contain at least one nitrogen and be bound to X.sub.a through nitrogen;
- and
- (g) when X.sub.a is CO then E.sub.1 is a single bond.
31 more elements
Dependencies are inferred from the claim text.