# US 4,243,409 A · 1,2,4-Oxadiazole derivatives and herbicide composition containing same

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 4,243,409 A
- Document ID: US4243409A
- Status: Granted
- Kind: A
- Application number: 06/001,157
- Filed: 1979-01-04
- Granted: 1981-01-06
- Earliest claimed: 1978-01-12
- Assignees: Schering Corporation
- Inventors: Erich Schmidt; Friedrich Arndt
- Web page: https://patentgrep.com/patent/US4243409A

## CPC

- C07D 271/06: 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- A01N 43/82: five-membered rings with three ring hetero atoms
- A01N 47/20: N-Aryl derivatives thereof
- A01N 47/30: Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
- 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 1,2,4-oxadiazole derivative of the formula ##STR1## in which R.sub.1 and R.sub.2 are the same or different and are C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, halogeno-C.sub.1 -C.sub.3 -alkyl, phenyl, or phenyl substituted in one or several places by C.sub.1 -C.sub.4 alkyl, and/or C.sub.1 -C.sub.4 -alkoxy and/or trihalogenomethyl and/or halogen and/or cyano or are phenyl-C.sub.1 -C.sub.3 -alkyl, provided that at least one of R.sub.1 or R.sub.2 is constituted by the group ##STR2## in which R.sub.3 is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, halogeno-C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.4 -alkamino or di-C.sub.1 -C.sub.4 -alkamino. The compounds of the invention have a high activity against both mono- and di-cotyl weeds together with a high selectivity for agricultural plants such as rice, winter cereals, maize, cotton, sunflower, peanuts, soybeans, peas, alfalfa, clover and other leguminous plants. They may be applied in preemergence or postemergence application.

## Claims

### Claim 1

A selective herbicidal composition comprising about 5 to 95% by weight of at least one of compounds selected from the group consisting of 3-[3-(cyclopropylcarbonylamino)-phenyl]-5-tert.-butyl-1,2,4-oxadiazole, 3-[3-(butyrylamino)-phenyl]-5-tert.-butyl-1,2,4-oxadiazole, 5-chloromethyl-3-(3-cyclopropylcarbonylaminophenyl)-1,2,4-oxadiazole, 3-(3-cyclopropylcarbonylaminophenyl)-5-methyl-1,2,4-oxadiazole, and 3-(3-cyclopropylcarbonylaminophenyl)-5-trifluoromethyl-1,2,4-oxadiazole; and about 95 to 5% by weight of a liquid or solid carrier material.

### Claim 2 (depends on 1)

The herbicidal composition of claim 1 which includes up to 20% by weight of a surface active agent upon a corresponding reduction of the liquid or solid carrier materials.

### Claim 3

The compound which is 3-[3-(cyclopropylcarbonylamino)-phenyl]-5-tert.-butyl-1,2,4-oxadiazole.

### Claim 4

The compound which is 3-[3-(butylrylamino)-phenyl]-5-tert.-butyl-1,2,4-oxadiazole.

### Claim 5

The compound which is 5-chloromethyl-3-(3-cyclopropylcarbonylaminophenyl)-1,2,4-oxadiazole.

### Claim 6

The compound which is 3-(3-cyclopropylcarbonylaminophenyl)-5-methyl-1,2,4-oxadiazole.

### Claim 7

The compound which is 3-(3-cyclopropylcarbonylaminophenyl)-5-trifluoromethyl-1,2,4-oxadiazole.