# US 4,398,939 A · Herbicidal thiophenesulfonamides

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- Number: US 4,398,939 A
- Document ID: US4398939A
- Status: Granted
- Kind: A
- Application number: 06/255,226
- Filed: 1981-05-04
- Granted: 1983-08-16
- Earliest claimed: 1979-04-04
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: George Levitt
- Web page: https://patentgrep.com/patent/US4398939A

## CPC

- C07D 521/00: Heterocyclic compounds containing unspecified hetero rings
- A01N 47/36: containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
- C07D 333/28: Halogen atoms
- C07D 333/34: Sulfur atoms
- 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

This invention covers thiophenesulfonylureas of Formula I, agriculturally suitable compositions containing them, and their method-of-use as general and/or selective preemergent and/or postemergent herbicides or plant growth regulants. The compound N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-3-chloro-2-thiophenesu lfonamide is typical of this cla

## Claims

### Claim 1

A compound of the formula: ##STR129## wherein A is SO.sub.2 N(R.sub.3)C(O)N(R.sub.4)R.sub.5 ;
R is C.sub.1 -C.sub.4 alkyl, C.sub.3 alkenyl, OCH.sub.3, NO.sub.2, Cl, Br, SO.sub.2 NR.sub.1 R.sub.2 and SO.sub.2 N(OCH.sub.3)CH.sub.3 ;
R.sub.1 and R.sub.2 are independently C.sub.1 -C.sub.3 alkyl;
R.sub.3 is H or CH.sub.3 ;
R.sub.4 is H, CH.sub.3 or OCH.sub.3 ;
R.sub.5 is ##STR130## 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, CH.sub.2 OCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2 or OCH.sub.2 C.tbd.CH;
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 ;
Y.sup.1 is H, CH.sub.3, OCH.sub.3 or Cl;
X.sup.2 and Y.sup.2 are independently CH.sub.3 or OCH.sub.3 ; and
Q is O or CH.sub.2 ; and their agricultural salts;
provided that
(a) A cannot be in the 4-position of the thiophene ring; and
(b) one of R.sub.3 or R.sub.4 must be H; and
(c) when A is in the 3-position and R is in the 2-position, then R is other than Cl, Br or CH.sub.3.

### Claim 2 (depends on 1)

A compound of claim 1 wherein R.sub.3 is H, and R.sub.4 is H or CH.sub.3.

### Claim 3 (depends on 2)

A compound of claim 2 wherein Z is CH and Q is O.

### Claim 4 (depends on 3)

A compound of claim 3 with the formula ##STR131##

### Claim 5 (depends on 3)

A compound of claim 3 with the formula ##STR132##

### Claim 6 (depends on 3)

A compound of claim 3 with the formula ##STR133##

### Claim 7 (depends on 4)

A compound of claim 4 wherein X is H, Cl, CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; and Y.sup.1 is CH.sub.3 or OCH.sub.3.

### Claim 8 (depends on 5)

A compound of claim 5 wherein X is H, Cl, CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; and Y.sup.1 is CH.sub.3 or OCH.sub.3.

### Claim 9 (depends on 6)

A compound of claim 6 wherein X is H, Cl, CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; and Y.sup.1 is CH.sub.3 or OCH.sub.3.

### Claim 10 (depends on 7)

A compound of claim 7 wherein R is CH.sub.3, NO.sub.2, Cl, Br or SO.sub.2 N(CH.sub.3).sub.2.

### Claim 11 (depends on 8)

A compound of claim 8 wherein R is CH.sub.3, NO.sub.2, Cl, Br or SO.sub.2 N(CH.sub.3).sub.2.

### Claim 12 (depends on 9)

A compound of claim 9 wherein R is CH.sub.3, Cl, Br or SO.sub.2 N(CH.sub.3).sub.2.

### Claim 13 (depends on 10)

A compound of claim 10 wherein R.sub.5 is ##STR134##

### Claim 14 (depends on 12)

A compound of claim 12 wherein R.sub.5 is ##STR135##

### Claim 15 (depends on 13)

A compound of claim 13 wherein X is CH.sub.3 or OCH.sub.3, and R.sub.4 is H.

### Claim 16 (depends on 1)

The compound of claim 1, N-[(4-methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]-3-chloro-2-thiophenesu lfonamide.

### Claim 17 (depends on 1)

The compound of claim 1, N-[(4,6-dimethyl-2-pyrimidinyl)aminocarbonyl]-3-chloro-2-thiophenesulfonam ide.

### Claim 18 (depends on 1)

The compound of claim 1, N-[(4,6-dimethoxy-2-pyrimidinyl)aminocarbonyl]-3-chloro-2-thiophenesulfona mide.

### Claim 19 (depends on 1)

The compound of claim 1, N-[(4-methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]-3-bromo-2-thiophenesul fonamide.

### Claim 20 (depends on 1)

The compound of claim 1, N-(4,6-dimethyl-2-pyrimidinyl)aminocarbonyl]-3-bromo-2-thiophenesulfonamid e.

### Claim 21 (depends on 1)

The compound of claim 1, N-(4,6-dimethoxy-2-pyrimidinyl)aminocarbonyl]-3-bromo-2-thiophenesulfonami de.

### Claim 22 (depends on 1)

The compound of claim 1, N-[(4-methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]-3-methyl-2-thiophenesu lfonamide.

### Claim 23 (depends on 1)

The compound of claim 1, N-[(4,6-dimethyl-2-pyrimidinyl)aminocarbonyl]-3-methyl-2-thiophenesulfonam ide.

### Claim 24 (depends on 1)

The compound of claim 1, N-[(4,6-dimethoxy-2-pyrimidinyl)aminocarbonyl]-3-methyl-2-thiophenesulfona mide.

### Claim 25 (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 26 (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 27 (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 28 (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 29 (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 30 (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 31 (depends on 7)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.

### Claim 32 (depends on 8)

A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 8 and at least one of the following: surfactant, solid or liquid diluent.

### Claim 33 (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 34 (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 35 (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 36 (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 37 (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 38 (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.

### Claim 39 (depends on 7)

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 7.

### Claim 40 (depends on 8)

A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim 8.

### Claim 41

A compound selected from: ##STR136## wherein B is ##STR137## R is C.sub.1 -C.sub.4 alkyl, C.sub.3 alkenyl, OCH.sub.3, NO.sub.2, Cl, Br, SO.sub.2 NR.sub.1 R.sub.2 or SO.sub.2 N(OCH.sub.3)CH.sub.3 ;
R.sub.1 and R.sub.2 are independently C.sub.1 -C.sub.3 alkyl;
Z is CH, CCl, CBr, CCN, CCH.sub.3, CCH.sub.2 CH.dbd.CH.sub.2, CCH.sub.2 CH.sub.3, or CCH.sub.2 CH.sub.2 Cl
provided that
(a) B may not be in the 4-position of the thiophene ring; and
(b) when B is in the 3-position and R is in the 2-position, then R is other than Cl, Br or CH.sub.3.