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US 5,393,733 AGranted
Herbicidal pyridinesulfonylureas
AssigneeE. I. Du Pont de Nemours and Company
InventorPaul H. Liang
Life of this patent
Estimating the term…
Abstract
This invention relates to herbicidal pyridinesulfonylureas which are highly active as preemergence and postemergence herbicides.
Claims10
A compound selected from ##STR58## wherein J is ##STR59## R is H or CH.sub.3 ;
- W is O or S;
- R.sub.1 is R.sub.f or R.sub.g ;
- R.sub.f is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio or CN;
- R.sub.g is C.sub.1 -C.sub.3 haloalkyl, cyclopropyl, C.sub.1 -C.sub.3 alkyl substituted by C.sub.1 -C.sub.3 alkoxy, OH, C.sub.1 -C.sub.2 alkylthio or CN, CN, W.sub.2 R.sub.11, amino, C.sub.1 -C.sub.3 alkylamino or C.sub.1 -C.sub.3 dialkylamino;
- R.sub.2 is C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.3 -C.sub.5 cycloalkylthio, C.sub.3 -C.sub.5 cycloalkylsulfinyl, C.sub.3 -C.sub.5 cycloalkylsulfonyl, SO.sub.2 NH.sub.2, SO.sub.2 NR.sub.d R.sub.e, SO.sub.2 NR'.sub.7 R.sub.8, SO.sub.2 NR.sub.7 R.sub.8, OSO.sub.2 R.sub.8, SO.sub.2 OR.sub.8, N.sub.3, P(W.sub.1)(OC.sub.1 -C.sub.2 alkyl).sub.2, CN, CO.sub.2 R.sub.9, CO.sub.2 R'.sub.9, CH.sub.2 F, CF.sub.2 H, CH.sub.2 Cl, CCl.sub.2 H or C.sub.2 -C.sub.4 haloalkyl;
- R.sub.7 is H, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl;
- R'.sub.7 is C.sub.1 -C.sub.4 alkyl;
- R.sub.8 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 alkoxyalkyl or cyclopropyl;
- or
- R.sub.7 and R.sub.8 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.9 is CH.sub.2 CH.sub.2 R.sub.10, CH.sub.2 CF.sub.3, C.sub.3 -C.sub.4 haloalkyl, C.sub.3 -C.sub.4 alknyl, C.sub.2 -C.sub.4 alkylthioalkyl, C.sub.3 -C.sub.5 cycloalkyl or C.sub.4 -C.sub.7 cycloalkylalkyl;
- R'.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 Br, CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 ;
- R.sub.10 is OH, F, CN, OSO.sub.2 (C.sub.1 -C.sub.3 alkyl) or OSO.sub.2 (C.sub.1 -C.sub.3 haloalkyl);
- R.sub.11 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl;
- W.sub.1 is O or S;
- W.sub.2 is O or S;
- A is ##STR60## 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.2 -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.2 -C.sub.4 haloalkoxy, C.sub.2 -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.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, azido, ##STR61## N(OCH.sub.3)CH.sub.3 ;
- m is 2 or 3;
- Q.sub.1 and Q.sub.2 are independently O or S;
- R.sub.a is H or C.sub.1 -C.sub.3 alkyl;
- R.sub.b and R.sub.c are independently C.sub.1 -C.sub.3 alkyl;
- R.sub.d is H or C.sub.1 -C.sub.2 alkyl;
- R.sub.e is C.sub.1 -C.sub.2 alkoxy;
- Z is CH;
- and their agriculturally suitable salts;
- provided that
- 1) when X is halogen, then Y is OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or N(OCH.sub.3)CH.sub.3 ;
- 2) 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.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, ##STR62## 3) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of R.sub.1 or R.sub.2 is less than or equal to six;
- 4) when R.sub.2 is C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, SO.sub.2 NR.sub.d R.sub.e, SO.sub.2 NR'.sub.7 R.sub.8 or CO.sub.2 R'.sub.9, then Y is other than C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, ##STR63## 5) when R.sub.2 is CO.sub.2 R'.sub.9 or SO.sub.2 NR'.sub.7 R, then R.sub.1 is R.sub.g and when R.sub.2 is other than CO.sub.2 R'.sub.9 or SO.sub.2 NR'.sub.7 R.sub.8, then R.sub.1 is R.sub.f ;
- 6) when J is J-1;
- R is H or CH.sub.3 ;
- X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F, Br, I, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br;
- Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, 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, C(O)R.sub.a, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3 ;
- R.sub.a is H or CH.sub.3 ;
- Z is CH;
- W is O;
- R.sub.1 is R.sub.f ;
- and
- R.sub.f is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 haloalkyl, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 thioalkyl;
- then
- R.sub.2 is other than C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl and
- 7) when J is J-1;
- W is O;
- R is H or CH.sub.3 ;
- R.sub.1 is R.sub.f or R.sub.g ;
- R.sub.f is C.sub.1 haloalkyl, halogen or OCH.sub.3 ;
- R.sub.g is C.sub.1 -C.sub.2 haloalkyl or W.sub.2 R.sub.11 ;
- W.sub.2 is O or S;
- R.sub.9 is CH.sub.2 CH.sub.2 R.sub.10, CH.sub.2 CF.sub.3, C.sub.3 -C.sub.4 haloalkyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 alkylthioalkyl, C.sub.3 -C.sub.5 cycloalkyl or C.sub.4 -C.sub.7 cycloalkylalkyl;
- R'.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, CH.sub.2 CH.sub.2 Cl, CH.sub.2 CH.sub.2 Br, CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 ;
- R.sub.10 is OH, F, CN, OSO.sub.2 (C.sub.1 -C.sub.3 alkyl) or OSO.sub.2 (C.sub.1 -C.sub.3 haloalkyl);
- R.sub.11 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 haloalkyl;
- A is A-1;
- X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F, Br, I, CH.sub.2 F, CF.sub.3, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br;
- Y is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, 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, C(O)R.sub.a, cyclopropyl, C.tbd.CH or C.tbd.CCH.sub.3 ;
- R.sub.a is H or CH.sub.3 ;
- and
- Z is CH;
- then
- R.sub.2 is other than CN, CO.sub.2 R.sub.9, CO.sub.2 R'.sub.9.
58 more elements
Dependencies are inferred from the claim text.