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US 4,732,604 AGranted
Herbicidal sulfonamides
AssigneeE. I. Du Pont de Nemours and Company
InventorsJames V. Hay, Barry A. Wexler, Donna F. Zimmerman
Life of this patent
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Abstract
This invention relates to certain sulfonylurea compounds having substituents ortho to the sulfonylurea linkage that includes a 3- or 4- membered carbocyclic ring, a saturated 5- or 6- membered carbocyclic ring or a heterocyclic ring which contains 1 heteroatom selected from O, S and NR.sub.3, agriculturally suitable compositions thereof and a method of their use as herbicides or plant growth regulants.
Claims27
A compound of the formula ##STR53## wherein W is O or S;
- R is H or CH.sub.3 ;
- L is ##STR54## n is 0 or 1;
- R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, CN, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sup.I R.sup.II, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CO.sub.2 R.sup.III, CH.sub.2 CN, CH.sub.2 OCH.sub.3 or CH.sub.2 SCH.sub.3 ;
- R.sup.I is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy;
- R.sup.II is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl;
- or
- R.sup.I and R.sup.II 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.sup.III 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.2 is C.sub.1 -C.sub.3 alkyl;
- Q is a 3- or 4-membered heterocyclic ring which contains one heteroatom selected from O, S and NR.sub.3, or a 3- or 4-membered carbocyclic ring in which one carbon atom may optionally be in the form of a carbonyl group, or a fully-saturated 5- or 6-membered carbocyclic ring, and Q may be optionally substituted with 1-4 substituents selected from halogen, CN, OH, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.2 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, (C.sub.1 -C.sub.4 alkyl)-aminosulfamoyl and di(C.sub.1 -C.sub.4 alkyl)aminosulfamoyl;
- R.sub.3 is C.sub.1 -C.sub.4 alkyl;
- R.sub.12 is H or OR.sub.14 ;
- R.sub.13 is H or C.sub.1 -C.sub.4 alkyl;
- R.sub.14 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 haloalkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.4 haloalkynyl, C.sub.2 -C.sub.4 alkylcarbonyl, C(O)NR.sub.15 R.sub.16, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.4 alkoxyalkyl or C.sub.2 -C.sub.4 alkylthioalkyl;
- R.sub.15 and R.sub.16 are independently H or C.sub.1 -C.sub.2 alkyl;
- A is ##STR55## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -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, 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 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.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, ##STR56## 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.4 and R.sub.5 are independently C.sub.1 -C.sub.2 alkyl;
- R.sub.6 is H or CH.sub.3 ;
- 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 L is L-2 or L-3, then the Q substituent and the sulfonylurea bridge are on adjacent carbon atoms;
- (c) when W is S, then R is H, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H, 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 .tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3 or CH(OCH.sub.3).sub.2 ;
- (d) the total number of carbon atoms of R.sub.12 and R.sub.13 must be less than or equal to four;
- and
- (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 Q must be less than or equal to six.
26 more elements
Dependencies are inferred from the claim text.