# US 5,352,654 A · Pyridyl sulfonylurea herbicides

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- Number: US 5,352,654 A
- Document ID: US5352654A
- Status: Granted
- Kind: A
- Application number: 07/530,690
- Filed: 1990-05-30
- Granted: 1994-10-04
- Earliest claimed: 1989-06-06
- Assignees: Ciba-Geigy Corporation
- Inventors: Werner Fory; Rolf Schurter
- Web page: https://patentgrep.com/patent/US5352654A

## 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: 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

N-Pyridinesulfonyl-N'-pyrimidinyl- and -triazinylureas of the formula I ##STR1## in which R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 C.sub.4 haloalkoxy or CF.sub.3 ; R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; A is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each of which is monosubstituted to trisubstituted by halogen, or is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each of which is substituted by C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.2 -C.sub.4 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl, amino, C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 dialkylamino or C.sub.2 -C.sub.4 alkynyl, it being possible for the C.sub.2 -C.sub.4 alkenyl radical and the C.sub.5 -C.sub.6 cycloalkenyl radical to be additionally monosubstituted to trisubstituted by halogen; or A is a 4- to 6-membered saturated heterocycle which contains a hetero atom selected from the group comprising O, N and SO.sub.2 ; or A is C.sub.1 -C.sub.4 alkyl which is substituted by a 4- to 6-membered saturated heterocycle which contains a hetero atom selected from the group comprising O, N and SO.sub.2 ; X is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkyl which is monosubstituted to trisubstituted by halogen, or is C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkoxy which is monosubstituted to trisubstituted by halogen; Y is halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkyl which is monosubstituted to trisubstituted by halogen, or is C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkoxy which is monosubstituted to trisubstituted by halogen, or is cyclopropyl, methylamino or dimethylamino; and E is nitrogen or the methine group, and the salts of these compounds with amines, alkali metal bases or alkaline earth metal bases or with quaternary ammonium bases have good selective herbicidal properties pre-emergence and post-emergence, and good growth-regulating properties.

## Claims

### Claim 1

An N-pyridinesulfonyl-N'-pyrimidinyl- or -triazinylurea of the formula I ##STR203## in which R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkoxy or CF.sub.3 ; R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; A is C.sub.1 -C.sub.4 alkyl which is substituted by C.sub.2 -C.sub.4 alkenyl, it being possible for the C.sub.2 -C.sub.4 alkenyl radical to be additionally monosubstituted to trisubstituted by halogen; X is C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkoxy which is monosubstituted to trisubstituted by halogen; Y is halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkoxy which is monosubstituted to trisubstituted by halogen, or is cyclopropyl; and E is nitrogen or the methine group, or a salt thereof.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio or CF.sub.3.

### Claim 3 (depends on 1)

A compound according to claim 1, wherein R.sub.2 is hydrogen.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein Y is chlorine, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkoxy which is monosubstituted to trisubstituted by halogen.

### Claim 5 (depends on 1)

A compound of the formula I according to claim 1, wherein X is methoxy, ethoxy or difluoromethoxy; and Y is methoxy, ethoxy, difluoromethoxy or chlorine.

### Claim 6 (depends on 1)

A compound of the formula I according to claim 1, wherein X is methoxy or ethoxy; and Y is methoxy.

### Claim 7 (depends on 1)

A compound of the formula I according to claim 1, wherein E is the methine bridge.

### Claim 8 (depends on 1)

A compound of the formula I according to claim 1, wherein R.sub.1 is hydrogen, methyl, methoxy, fluorine or chlorine.

### Claim 9 (depends on 1)

A compound of the formula I according to claim 1, wherein R.sub.1 and R.sub.2 are hydrogen.

### Claim 10 (depends on 1)

A compound of the formula I according to claim 1 wherein A is allyl, methallyl, 2-methylpropenyl or 3-chloroallyl.

### Claim 11 (depends on 10)

A compound of the formula I according to claim 10, wherein R.sub.1 and R.sub.2 are hydrogen.

### Claim 12 (depends on 1)

A compound of the formula I according to claim 1, wherein R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 -haloalkoxy or CF.sub.3 ; R.sub.2 is hydrogen or C.sub.1 -C.sub.2 alkyl; A is C.sub.1 -C.sub.2 alkyl which is substituted by C.sub.2 -C.sub.3 alkenyl, it being possible for the C.sub.2 -C.sub.3 alkenyl radical to be additionally monosubstituted to trisubstituted by halogen; X is C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkoxy which is monosubstituted to trisubstituted by halogen; Y is halogen, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkoxy which is monosubstitued to trisubstituted by halogen, or is cyclopropyl.

### Claim 13 (depends on 12)

A compound of the formula I according to claim 12, wherein R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkylthio or CF.sub.3.

### Claim 14 (depends on 1)

A compound of the formula I according to claim 1, wherein R.sub.1 and R.sub.2 are hydrogen and A is C.sub.1 -C.sub.2 alkyl which is substituted by C.sub.2 -C.sub.4 alkenyl, it being possible for the C.sub.2 -C.sub.4 alkenyl radical to be additionally monosubstituted to trisubstituted by fluorine or chlorine.

### Claim 15 (depends on 11)

A compound according to claim 11, wherein A is allyl, methallyl or 3-chloroallyll; X is methoxy, ethoxy or difluoromethoxy and Y is methoxy, ethoxy, difluoromethoxy or chlorine.

### Claim 16

N-(3-Allylsulfonylpyridin-2-ylsul fonyl)N'-(4,6-dimethoxypyrimidin-2-yl)urea.

### Claim 17 (depends on 1)

A herbicidal and growth-inhibiting composition, which contains at least an effective amount of a sulfonylurea of the formula I, according to claim 1 and a carrier therefor.

### Claim 18 (depends on 1)

A method for controlling undesired plant growth, wherein an active substance of the formula I, according to claim 1, or a composition containing this active substance, is applied in an effective amount to the plants or their environment.

### Claim 19 (depends on 18)

A method according to claim 18, wherein an amount of active substance of between 0.001 and 5 kg per hectare is applied.

### Claim 20 (depends on 1)

A method for inhibiting plant growth, wherein an active substance of the formula I, according to claim 1, or a composition containing this active substance, is applied in an effective amount to the plants or their environment.

### Claim 21 (depends on 1)

A method for influencing plant growth with the purpose of increasing the yield, wherein an active substance of the formula I, according to claim 1, or a composition containing this active substance, is applied in an effective amount to the plants or their environment.

### Claim 22 (depends on 18)

A method according to claim 18 for selective weed control in crops, either pre- or post-emergence.

### Claim 23 (depends on 17)

A composition according to claim 17 wherein the sulfonylurea comprises between 0.1% and 95% of the mixture.