# US 11,304,418 B2 · Substituted n-(-1,3,4-oxadiazole-2-yl)aryl carboxamides and the use thereof as herbicides

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

- Number: US 11,304,418 B2
- Document ID: US11304418B2
- Status: Granted
- Kind: B2
- Application number: 16/497,814
- Filed: 2018-03-22
- Published: 2021-03-18
- Granted: 2022-04-19
- Earliest claimed: 2017-03-30
- Assignees: Bayer CropScience AG
- Applicants: Bayer CropScience Aktiengesellschaft
- Inventors: Arnim Koehn; Hartmut Ahrens; Christian Waldraff; Ralf Braun; Stephen David Lindell; Anu Bheemaiah Machettira; Elmar Gatzweiler; Christopher Hugh Rosinger; Hansjoerg Dietrich
- Web page: https://patentgrep.com/patent/US11304418B2

## CPC

- A01N 43/82: five-membered rings with three ring hetero atoms
- C07D 271/113: with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Disclosed are N-(1,3,4-oxadiazole-2-yl)aryl carboxamides of formula (I) or the salts (I) thereof as well as the use thereof as herbicides.

## Claims

### Claim 1

An N-(1,3,4-oxadiazol-2-yl)arylcarboxamide of formula (I) or salt thereof
wherein the substituents have the following meanings:
A represents N or C—Y,
R represents hydrogen or (C1-C6)-alkyl,
X represents halogen or (C1-C6)-alkyl,
Y represents halogen, (C1-C6)-alkyl, C(O)N(R1)2, S(O)nR2, or 2-oxoazetidin-1-yl,
Z represents halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, or R2(O)nS,
V represents hydrogen, halogen or (C1-C6)-alkyl,
W represents hydrogen, halogen or (C1-C6)-haloalkyl,
with the proviso that in each case at least one of the radicals V and W does not represent hydrogen,
R1 represents hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, or (C3-C6)-cycloalkyl-(C1-C6)-alkyl,
R2 represents (C1-C6)-alkyl, and
n represents 0, 1 or 2,
with the proviso that the compounds
4-bromo-2,6-difluoro-2-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide and
4-bromo-2,6-difluoro-2-N-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)benzamide
are excluded.

### Claim 2 (depends on 1)

The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 1, wherein
R represents hydrogen, or (C1-C4)-alkyl,
V represents hydrogen, halogen, or (C1-C4)-alkyl, and
W represents halogen or (C1-C4)-haloalkyl.

### Claim 3 (depends on 1)

The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 1, wherein
R represents hydrogen, methyl, or ethyl,
X represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, or isopropyl,
Y represents fluorine, chlorine, bromine, iodine, (C1-C6)-alkyl, or 2-oxoazetidin-1-yl,
Z represents fluorine, chlorine, bromine iodine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, or heptafluoroisopropyl,
V represents hydrogen, fluorine, or methyl and,
W represents fluorine.

### Claim 4 (depends on 1)

The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 1, wherein
A represents C—Y,
V represents hydrogen, and
W represents fluorine.

### Claim 5 (depends on 1)

The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 1, wherein
A represents C—Y,
R represents hydrogen, methyl, or ethyl,
X represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, or isopropyl,
V represents hydrogen, and
W represents fluorine.

### Claim 6 (depends on 5)

The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 5, wherein
Y represents S(O)nR2, and
Z represents trifluoromethyl, difluoromethyl or pentafluoroethyl.

### Claim 7 (depends on 5)

The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 5, wherein
X represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, or isopropyl,
Y represents fluorine, chlorine, methyl ethyl, propyl, isopropyl, CONMe2, S(O)Me, S(O)Et, So2Me, or SO2Et,
and
Z represents fluorine, chlorine, bromine, iodine, CF3, SMe, SEt, SOMe, SOEt, SO2Me, or SO2Et.

### Claim 8 (depends on 1)

The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide as claimed in claim 1, wherein
A represents N,
V represents hydrogen,
W represents fluorine, and
Z represents CF3.

### Claim 9 (depends on 1)

An herbicidal composition, comprising an herbicidally active content of at least one compound of formula (I) as claimed in claim 1.

### Claim 10 (depends on 9)

The herbicidal composition as claimed in claim 9 in a mixture with one or more formulation auxiliaries.

### Claim 11 (depends on 9)

The herbicidal composition as claimed in claim 9, comprising at least one further pesticidally active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners, and growth regulators.

### Claim 12 (depends on 11)

The herbicidal composition as claimed in claim 11, comprising a safener.

### Claim 13 (depends on 12)

The herbicidal composition as claimed in claim 12, comprising cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.

### Claim 14 (depends on 9)

The herbicidal composition as claimed in claim 9, comprising a further herbicide.

### Claim 15 (depends on 1)

A method for controlling monocotyledonous or dicotyledonous weeds, comprising applying an effective amount of at least one compound of formula (I) as claimed in claim 1 or of a herbicidal composition comprising the at least one compound of formula (I) is applied to the weeds or to the site of the weeds.

### Claim 16 (depends on 1)

A product comprising the compound of formula (I) as claimed in claim 1 or an herbicidal composition comprising the compound of formula (I) for controlling one or more monocotyledonous or dicotyledonous weeds.