# US 5,348,933 A · Substituted pyridinesulfonamide compound or its salt, process for preparing the same, and herbicide containing the same

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- Number: US 5,348,933 A
- Document ID: US5348933A
- Status: Granted
- Kind: A
- Application number: 08/028,165
- Filed: 1993-03-09
- Granted: 1994-09-20
- Earliest claimed: 1991-01-24
- Assignees: Ishihara Sangyo Kaisha, Ltd.
- Inventors: Nobuyuki Sakashita; Toshio Nakajima; Shigeo Murai; Kazuyuki Maeda; Yuji Nakamura; Tsunezo Yoshida; Shooichi Honzawa; Fumio Kanamori
- Web page: https://patentgrep.com/patent/US5348933A

## CPC

- C07D 213/75: Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- A01N 47/36: containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
- C07D 213/76: to which a second hetero atom is attached (nitro radicals C07D213/61)
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 521/00: Heterocyclic compounds containing unspecified hetero rings
- 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

A substituted pyridinesulfonamide compound or its salt represented by the following general formula (I): ##STR1## wherein A is CH or N; when A is CH, R.sub.1 and R.sub.2 may be either each independently a member selected from the group consisting of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkenyl groups, unsubstituted or substituted cycloalkyl groups, and unsubstituted or substituted phenyl groups; when A is N, R.sub.1 is an unsubstituted or substituted alkyl group, R.sub.2 is an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group; and X and Y are each independently a member selected from the group consisting of alkyl groups and alkoxy groups, is disclosed. This compound is useful as the effective ingredient of a herbicide showing a wide weed-control spectrum even if used in a small amount.

## Claims

### Claim 1

A pyridinesulfonamide compound or its salt represented by the following formula (I): ##STR34## wherein A is N; R.sub.1 is a C.sub.1-4 alkyl group which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms and C.sub.1-4 alkoxy groups; R.sub.2 is a C.sub.1-4 alkyl group which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms and C.sub.1-4 alkoxy groups, or a C.sub.1-4 alkoxy group which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms and C.sub.1-4 alkoxy groups; and X and Y are each independently a member selected from the group consisting of C.sub.1-4 alkyl groups and C.sub.1-4 alkoxy groups.

### Claim 2 (depends on 1)

The compound or the salt thereof as in claim 1, wherein X and Y are each independently a member selected from the group consisting of a methyl group and a methoxy group.

### Claim 3 (depends on 1)

The compound or the salt thereof as in claim 1, wherein R.sub.1 and R.sub.2 are each independently an ethyl, propyl or butyl group, and X and Y are each independently a member selected from the group consisting of a methyl group and a methoxy group.

### Claim 4 (depends on 1)

The compound or the salt thereof as in claim 1, which is 6-[(N-ethyl-N-isopropylsulfonyl)amino]-N-[[(4-methoxy-6-methyltriazin-2-yl )amino]carbonyl]-2-pyridinesulfonamide, 6-[(N-ethyl-N-isopropylsulfonyl)amino]-N-[[(4,6-dimethoxytriazin-2-yl)amin o]carbonyl]-2-pyridinesulfonamide, 6-[[N-(1-chloroethylsulfonyl)-N-ethyl]amino]-N-[[(4-methoxy-6-methyltriazi n-2-yl)amino]carbonyl]-2-pyridinesulfonamide, 6-[[N-(1-chloroethylsulfonyl)-N-ethyl]amino]-N-[[(4,6-dimethoxytriazin-2-y l)amino]-carbonyl]-2-pyridinesulfonamide or 6-[(N-dichloromethylsulfonyl-N-ethyl)amino]-N-[[(4,6-dimethoxytriazine-2-y l)amino]carbonyl]-2-pyridinesulfonamide.

### Claim 5 (depends on 1)

The compound or the salt thereof as in claim 1, which is 6-[[N-(1-chloroethylsulfonyl)-N-ethyl]-amino]-N-[[(4-methoxy-6-methyltriaz in-2-yl)amino]carbonyl]-2-pyridinesulfonamide.

### Claim 6

A herbicide composition containing an agricultural adjuvant and as an effective ingredient a pyridinesulfonamide compound represented by the following formula (I) or its salt: ##STR35## wherein A is N; R.sub.1 is a C.sub.1-4 alkyl group which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms and C.sub.1-4 alkoxy groups; R.sub.2 is a C.sub.1-4 alkyl group which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms and C.sub.1-4 alkoxy groups, or a C.sub.1-4 alkoxy group which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms and C.sub.1-4 alkoxy groups; and X and Y are each independently a member selected from the group consisting of C.sub.1-4 alkyl groups and C.sub.1-4 alkoxy groups.

### Claim 7 (depends on 6)

The herbicide composition as in claim 6, wherein X and Y are each independently a member selected from the group consisting of a methyl group and a methoxy group.

### Claim 8 (depends on 6)

The herbicide composition as in claim 6, wherein R.sub.1 and R.sub.2 are each independently an ethyl, propyl or butyl group, and X and Y are each independently a member selected from the group consisting of a methyl group and methoxy group.

### Claim 9 (depends on 6)

The herbicide composition as in claim 6, wherein said effective ingredient is 6-[(N-ethyl-N-isopropylsulfonyl)amino]-N-[[(4-methoxy-6-methyltriazin-2-yl )amino]carbonyl]-2-pyridinesulfonamide, 6-[(N-ethyl-N-isopropylsulfonyl)amino]-N-[[(4,6-dimethoxytriazin-2yl)amino ]carbonyl]-2-pyridinesulfonamide, 6-[[N-(1-chloroethylsulfonyl)-N-ethyl]amino]-N-[[(4-methoxy-6-methyltriazi n-2-yl)amino]carbonyl]-2-pyridinesulfonamide, 6-[[N- (1-chloroethylsulfonyl)-N-ethyl]amino]-N-[[(4,6-dimethoxytriazin-2-yl)amin o]carbonyl]-2-pyridinesulfonamide or 6-[(N-dichloromethylsulfonyl-N-ethyl)amino]-N-[[(4,6-dimethoxytriazine-2-y l)amino]carbonyl]-2-pyridinesulfonamide.

### Claim 10 (depends on 6)

The herbicide composition as in claim 6, wherein said effective ingredient is 6-[[N-(1-chloroethylsulfonyl)-N-ethyl]amino]-N-[[(4-methoxy-6-methyltriazi n-2-yl)amino]carbonyl]-2-pyridinesulfonamide.

### Claim 11

A herbicidal method which comprises applying to plants a herbicidally effective amount of a pyridinesulfonamide compound or its salt represented by the following formula (I): ##STR36## wherein A is N; R.sub.1 is a C.sub.1-4 alkyl group which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms and C.sub.1-4 alkoxy groups; R.sub.2 is a C.sub.1-4 alkyl group which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms and C.sub.1-4 alkoxy groups, or a C.sub.1-4 alkoxy group which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms and C.sub.1-4 alkoxy groups; and X and Y are each independently a member selected from the group consisting of C.sub.1-4 alkyl groups and C.sub.1-4 alkoxy groups.