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US 4,906,283 AGranted
Herbicidal sulfonamides
AssigneeE. I. Du Pont de Nemours and Company
InventorJoel R. Christensen
Life of this patent
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Abstract
This invention relates to herbicidally active sulfonamide compounds having a heterocyclic carbonyl group ortho to the sulfonyl bridge.
Claims27
A compound of the formula ##STR69## wherein W is O or S;
- J is ##STR70## Q is ##STR71## G is a C.sub.1 -C.sub.3 alkyl radical in which one of the carbons must be substituted with R.sub.2 and/or R.sub.3, and the remaining carbon atoms may optionally be substituted with 1 or 2 substituents selected from CH.sub.3, F and Cl;
- R is H or CH.sub.3 ;
- 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.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 OCH.sub.3, CH.sub.2 SCH.sub.3, CH.sub.2 CN, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ;
- R.sub.2 is OH, OCH.sub.3 or OC.sub.2 H.sub.5 ;
- R.sub.3 is OCH.sub.3 or OC.sub.2 H.sub.5 ;
- or
- R.sub.2 and R.sub.3 can be taken together to form a carbonyl group, or the 5- or 6-membered ring ketal or thioketal thereof;
- 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.3 -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.7 and R.sub.8 are independently H, CH.sub.3, Cl or Br;
- R.sub.10 and R.sub.15 are independently H or CH.sub.3 ;
- A is ##STR72## 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.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, C(O)R.sub.4, ##STR73## 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.5 and R.sub.6 are independently C.sub.1 -C.sub.2 alkyl;
- R.sub.4 is H or CH.sub.3 ;
- and
- Z is CH;
- and their agriculturally suitable salts;
- provided that
- (a) when X is Cl, F, Br, or I, Y is OCH.sub.3, OCH.sub.2 CH.sub.3, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H;
- (b) when J is J-2 or J-3, then GQ and the sulfonylurea bridge must be on adjacent carbon atoms;
- (c) when Q is bonded to G through nitrogen, then the adjacent carbon atom of G cannot be substituted with OH, F or Cl;
- (d) when G is C.sub.1 alkyl in the form of a carbonyl group, then Q is other than ##STR74## (e) 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.1 and GQ must be less than or equal to ten;
- (f) when W is S, then R 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 or CH(OCH.sub.3).sub.2 ;
- and
- (g) when R.sub.3 is OCH.sub.3 or OC.sub.2 H.sub.5, the R.sub.2 is other than OH.
28 more elements
Dependencies are inferred from the claim text.