# US 4,397,679 A · Herbicidal o-sulfamylmethylbenzenesulfonamides

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- Number: US 4,397,679 A
- Document ID: US4397679A
- Status: Granted
- Kind: A
- Application number: 06/253,407
- Filed: 1981-04-27
- Granted: 1983-08-09
- Earliest claimed: 1980-07-11
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: Richard F. Sauers
- Web page: https://patentgrep.com/patent/US4397679A

## CPC

- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- A01N 47/36: containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
- C07D 239/47: One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- C07D 239/52: Two oxygen atoms
- C07D 239/70: condensed with carbocyclic rings or ring systems
- C07D 251/16: to only one ring carbon atom
- C07D 251/22: to two ring carbon atoms
- C07D 251/42: One nitrogen atom
- C07D 251/44: with halogen atoms attached to the two other ring carbon atoms
- C07D 251/46: with oxygen or sulfur atoms attached to the two other ring carbon atoms
- C07D 295/096: with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D 491/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

The compounds are of the class of N-[(substituted pyrimidin-2-yl)aminocarbonyl]-2-(sulfonylmethyl)benzenesulfonamides, useful as preemergent or postemergent herbicides or plant growth regulants.

## Claims

### Claim 1

A compound of the formula: ##STR36## wherein L is SO.sub.2 NR.sub.3 R.sub.4 ;
R is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy;
R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;
R.sub.2 is H or CH.sub.3 ;
R.sub.3 is C.sub.1 -C.sub.4 alkyl or OCH.sub.3 ;
R.sub.4 is C.sub.1 -C.sub.4 alkyl;
R.sub.8 is H, CH.sub.3 or OCH.sub.3 ;
A is ##STR37## W is O or S; X is H, Cl, Br, CH.sub.3, CH.sub.2 CH.sub.3, C.sub.1 -C.sub.3 alkoxy, CF.sub.3, SCH.sub.3 or CH.sub.2 OCH.sub.3 ;
Y is CH.sub.3 or OCH.sub.3 ;
Z is CH, CCl, CBr, CCN, CCH.sub.3, CCH.sub.2 CH.sub.3, CCH.sub.2 CH.sub.2 Cl or CCH.sub.2 CH.dbd.CH.sub.2 ;
and their agriculturally suitable salts;
provided that:
(1) when R.sub.3 is OCH.sub.3, then R.sub.4 is CH.sub.3 ;
(2) the total number of carbon atoms of R.sub.3 and R.sub.4 is five or less; and
(3) when W is S, then R.sub.8 is H.

### Claim 2 (depends on 1)

A compound of claim 1 wherein Z is CH, CCl, CBr or CCH.sub.3, W is O, and R.sub.8 is H or CH.sub.3.

### Claim 3 (depends on 2)

A compound of claim 2 wherein Z is CH, X is CH.sub.3 or OCH.sub.3, and R.sub.1 and R.sub.2 are H.

### Claim 4 (depends on 3)

A compound of claim 3 wherein A is ##STR38## and R and R.sub.8 are H.

### Claim 5 (depends on 4)

A compound of claim 4 wherein R.sub.3 is C.sub.1 -C.sub.3 alkyl or OCH.sub.3, and R.sub.4 is CH.sub.3.

### Claim 6 (depends on 5)

A compound of claim 5 wherein R.sub.3 is OCH.sub.3 or CH.sub.3.

### Claim 7 (depends on 1, 2)

The compound of claim 1, 2-[(dimethylamino)sulfonylmethyl]-N-[(4,6-dimethylpyrimidin-2-yl)aminocarb onyl]benzenesulfonamide.

### Claim 8 (depends on 1, 2)

The compound of claim 1, 2-[(dimethylamino)sulfonylmethyl]-N-[(4,6-dimethoxypyrimidin-2-yl)aminocar bonyl]benzenesulfonamide.

### Claim 9 (depends on 1, 2)

The compound of claim 1, 2-[(dimethylamino)sulfonylmethyl]-N-[(4-methoxy-6-methylpyrimidin-2-yl)ami nocarbonyl]benzenesulfonamide.

### Claim 10

A compound selected from: ##STR39## wherein L is SO.sub.2 NR.sub.3 R.sub.4 ;
R is H, F, Cl, Br, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy;
R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;
R.sub.2 is H or CH.sub.3 ;
R.sub.3 is C.sub.1 -C.sub.4 alkyl or OCH.sub.3 ;
R.sub.4 is C.sub.1 -C.sub.4 alkyl; and
Z is CH;
provided that:
(1) when R.sub.3 is OCH.sub.3, then R.sub.4 is CH.sub.3 ; and
(2) the total number of carbon atoms of R.sub.3 and R.sub.4 is five or less.

### Claim 11 (depends on 1)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.

### Claim 12 (depends on 2)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.

### Claim 13 (depends on 3)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.

### Claim 14 (depends on 4)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.

### Claim 15 (depends on 5)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.

### Claim 16 (depends on 6)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.

### Claim 17 (depends on 1)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 1.

### Claim 18 (depends on 2)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 2.

### Claim 19 (depends on 3)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 3.

### Claim 20 (depends on 4)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 4.

### Claim 21 (depends on 5)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 5.

### Claim 22 (depends on 6)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 6.