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US 5,512,535 AGranted
Herbicidal pyridinesulfonylureas
AssigneeE. I. Du Pont de Nemours and Company
InventorPaul Hsiao-Tseng Liang
Life of this patent
Estimating the term…
Abstract
This invention relates to herbicidal pyridinesulfonylureas which are highly active as preemergence and postemergence herbicides.
Claims14
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, C.sub.2 -C.sub.3 alkyl, 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.3 is C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.3 -C.sub.5 cycloalkylthio, C.sub.3 -C.sub.5 cycloalkylsulfinyl, C.sub.3 -C.sub.4 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, or C.sub.1 -C.sub.4 haloalkyl;
- R.sub.4 is C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.3 -C.sub.5 cycloalkylthio, C.sub.3 -C.sub.5 cycloalkylsulfinyl, C.sub.3 -C.sub.4 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, 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, or C.sub.1 -C.sub.4 haloalkyl;
- R.sub.5 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 cycloalkyl sulfonyl, SO.sub.2 NH.sub.2, SO.sub.2 NR.sub.d R.sub.e, 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) 2, CN, CO.sub.2 R.sub.9, or C.sub.1 -C.sub.4 haloalkyl;
- R.sub.6 is C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 haloalkylsulfinyl, C.sub.1 -C.sub.4 haloalkylsulfonyl, C.sub.3 -C.sub.4 alkenylthio, C.sub.3 -.sub.4 alkenylsulfinyl, C.sub.3 -.sub.4 alkenylsulfonyl, C.sub.3 -.sub.4 alkynylthio, C.sub.3 -.sub.4 alkynylsulfinyl, C.sub.3 -C.sub.4 alkynylsulfonyl, C.sub.3 -C.sub.5 cycloalkylthio, C.sub.3 -C.sub.5 cycloalkylsulfinyl, C.sub.3 -C.sub.5 cycloalkylsulfonyl, SO.sub.2 NR.sub.d R.sub.e, SO.sub.2 NR.sub.7 R.sub.8, OSO.sub.2 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, or C.sub.1 -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 -.sub.4 alkenyl, C.sub.3 -.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, 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## 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 N;
- X.sub.3 is CH.sub.3 or OCH.sub.3 ;
- and their agriculturally suitable salts;
- provided that
- 1) 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 ##STR62## 2) 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, R.sub.2, R.sub.3, R.sub.4, R.sub.5 or R.sub.6 is less than or equal to six;
- 3) when J is J-1 and 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, or when J is J-2 and R.sub.3 is C.sub.1 -C.sub.4 alkylsulfinyl, CF.sub.3, 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 alkoxy) alkoxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, ##STR63## 4) when J is J-2 or J-3 and R.sub.3 or R.sub.4 is C.sub.1 -C.sub.4 alkylsulfinyl, then X and Y are other than NH.sub.2 or NHCH.sub.3 ;
- 5) when J is J-2 and R.sub.3 is C.sub.1 -C.sub.4 alkylsulfinyl or SO.sub.2 NR.sub.d R.sub.e, or R.sub.7 is H, then X and Y are other than C.sub.2 -C.sub.4 haloalkoxy;
- 6) when J is J-5, then R.sub.7 is other than H and R.sub.6 is other than SO.sub.2 NR.sub.d R.sub.e ;
- 7) when J is J-2 and R.sub.7 is H or R.sub.3 is SO.sub.2 NR.sub.d R.sub.e, then Y is other than C.sub.2 -C.sub.4 alkynyl;
- 8) when R.sub.2 or R.sub.3 is CO.sub.2 R'.sub.9 or SO.sub.2 NR'.sub.7 R.sub.8, then R.sub.1 is R.sub.g and when R.sub.2 or R.sub.3 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 ;
- and
- 9) when J is J-2 and R.sub.1 is adjacent to the sulfonylurea bridge, then R.sub.g is C.sub.1 -C.sub.3 haloalkyl, C.sub.2 -C.sub.3 alkyl, cyclopropyl, CN, W.sub.2 R.sub.11, amino, C.sub.1 -C.sub.3 alkylamino or C.sub.1 -C.sub.3 dialkylamino.
36 more elements
Dependencies are inferred from the claim text.