US 4,786,311 AGranted

Herbicidal sulfonamides

AssigneeE. I. Du Pont de Nemours and Company

InventorGeorge Levitt

Life of this patent

Estimating the term…

Abstract

Tetrazole-substituted benzenesulfonamides are useful as agricultural chemicals and, in particular, as growth regulants and herbicides.

Claims83

Dependent claims

A compound of the formula:

##STR44## wherein J is ##STR45## W is O, S or NR.sub.X ;
R.sub.X is H, OH, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, allyloxy, propargyloxy, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 haloalkoxy or NR.sub.Y R.sub.Z ;
R.sub.Y is H or C.sub.1 -C.sub.3 alkyl;
R.sub.Z is C.sub.1 -C.sub.3 alkyl;
G is O, S, SO or SO.sub.2 ;
m is 0 or 1;
n is 0, 1 or 2;
R is H or CH.sub.3 ;
E is a single bond, CH.sub.2 or O;
Q is ##STR46## 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, CN, SCN, CO.sub.2 R.sub.c, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkylthio, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio or CN;
R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, allyl or phenyl;
R.sub.3 is H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.6 haloalkyl, CH.sub.2 -(C.sub.2 -C.sub.5 alkenyl), CH.sub.2 (C.sub.2 -C.sub.5 haloalkenyl), CH.sub.2 (C.sub.2 -C.sub.5 alkynyl), CH.sub.2 (C.sub.2 -C.sub.5 haloalkynyl), C.sub.6 H.sub.5 or C.sub.1 -C.sub.4 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfinyl or C.sub.1 -C.sub.2 alkylsulfonyl;
R.sub.4 is H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.6 H.sub.5, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, OCH.sub.2 CH.sub.2 O-(C.sub.1 -C.sub.2 alkyl) or di(C.sub.1 -C.sub.3 alkyl)amino;
R.sub.5 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, allyl or propargyl;
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.1 -C.sub.2 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl;
A is ##STR47## 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.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.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonyalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, azido, cyano ##STR48## or --N(OCH.sub.3)CH.sub.3 ;
p is 2 or 3;
L.sub.1 and L.sub.2 are independently O or S;
R.sub.6 is H or CH.sub.3 ;
R.sub.7 and R.sub.8 are independently C.sub.1 -C.sub.3 alkyl;
and
X.sub.3 is CH.sub.3 or OCH.sub.3 ;
and their agriculturally suitable salts;
provided that
(a) when J is J-9 and n is O, then Q is Q-1 or Q-2;
(b) when E is O, then J is J-1;
(c) when W is S, then A is A-1, 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.sub..tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR49## (d) when the total number of carbon atoms in X and Y is greater than 4, then the carbon content of R.sub.1, R.sub.3, R.sub.4 and R.sub.5 must each be less than or equal to 2;
(e) when J is J-1 and m is 0, then n is 0;
and
(f) when n is 0 and m is 1, then Q is Q-1 or Q-2.

32 more elements

Dependencies are inferred from the claim text.

Facts

Application: 06/114,584Filed 30 Oct 1987 · continuation in part
Priority: 30 May 1985
Granted: 22 Nov 1988
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 257/04
Not condensed with other rings: five-membered rings
A01N 47/36
Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<: containing the group >N—CO—N< directly attached to at least one heterocyclic ring;…
C07D 403/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
C07D 521/00
Heterocyclic compounds containing unspecified hetero rings

Family

Serial739,214Parent of this continuation-in-part · filed 30 May 1985
Serial849,618Parent of this continuation-in-part · filed 11 Apr 1986
Serial934,118Parent of this continuation-in-part · filed 24 Nov 1986
US 4,746,353 AParent of this continuation-in-part
US 4,786,311 AThis patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

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A compound of the formula:

##STR44## wherein J is ##STR45## W is O, S or NR.sub.X ;
R.sub.X is H, OH, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, allyloxy, propargyloxy, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 haloalkoxy or NR.sub.Y R.sub.Z ;
R.sub.Y is H or C.sub.1 -C.sub.3 alkyl;
R.sub.Z is C.sub.1 -C.sub.3 alkyl;
G is O, S, SO or SO.sub.2 ;
m is 0 or 1;
n is 0, 1 or 2;
R is H or CH.sub.3 ;
E is a single bond, CH.sub.2 or O;
Q is ##STR46## 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, CN, SCN, CO.sub.2 R.sub.c, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkylthio, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino or C.sub.1 -C.sub.2 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkylthio or CN;
R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, allyl or phenyl;
R.sub.3 is H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.6 haloalkyl, CH.sub.2 -(C.sub.2 -C.sub.5 alkenyl), CH.sub.2 (C.sub.2 -C.sub.5 haloalkenyl), CH.sub.2 (C.sub.2 -C.sub.5 alkynyl), CH.sub.2 (C.sub.2 -C.sub.5 haloalkynyl), C.sub.6 H.sub.5 or C.sub.1 -C.sub.4 alkyl substituted with C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfinyl or C.sub.1 -C.sub.2 alkylsulfonyl;
R.sub.4 is H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.6 H.sub.5, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, OCH.sub.2 CH.sub.2 O-(C.sub.1 -C.sub.2 alkyl) or di(C.sub.1 -C.sub.3 alkyl)amino;
R.sub.5 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, allyl or propargyl;
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.1 -C.sub.2 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl;
A is ##STR47## 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.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.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonyalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, azido, cyano ##STR48## or --N(OCH.sub.3)CH.sub.3 ;
p is 2 or 3;
L.sub.1 and L.sub.2 are independently O or S;
R.sub.6 is H or CH.sub.3 ;
R.sub.7 and R.sub.8 are independently C.sub.1 -C.sub.3 alkyl;
and
X.sub.3 is CH.sub.3 or OCH.sub.3 ;
and their agriculturally suitable salts;
provided that
(a) when J is J-9 and n is O, then Q is Q-1 or Q-2;
(b) when E is O, then J is J-1;
(c) when W is S, then A is A-1, 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.sub..tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR49## (d) when the total number of carbon atoms in X and Y is greater than 4, then the carbon content of R.sub.1, R.sub.3, R.sub.4 and R.sub.5 must each be less than or equal to 2;
(e) when J is J-1 and m is 0, then n is 0;
and
(f) when n is 0 and m is 1, then Q is Q-1 or Q-2.

32 more elements

Facts

Application

06/114,584Filed 30 Oct 1987 · continuation in part

Priority

30 May 1985

Granted

22 Nov 1988

Term ends

Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 257/04
Not condensed with other rings: five-membered rings
A01N 47/36
Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<: containing the group >N—CO—N< directly attached to at least one heterocyclic ring;…
C07D 403/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
C07D 521/00
Heterocyclic compounds containing unspecified hetero rings

Family

Serial739,214Parent of this continuation-in-part · filed 30 May 1985

Serial849,618Parent of this continuation-in-part · filed 11 Apr 1986

Serial934,118Parent of this continuation-in-part · filed 24 Nov 1986

US 4,746,353 AParent of this continuation-in-part

US 4,786,311 AThis patent

From the US filing history. Foreign family members aren’t listed.