3-acyl-benzamides and their use as herbicides

Patent metadata

Field	Value
Publication number	US-11051515-B2
Application number	US-201816633943-A
Country	US
Kind code	B2
Filing date	Aug 2, 2018
Priority date	Aug 4, 2017
Publication date	Jul 6, 2021
Grant date	Jul 6, 2021

Abstract

The invention relates to 3-acyl-benzamides of formula (I) as herbicides. In formulae (I) X, Y, Z and Rx represent radicals such as alkyl, cycloalkyl and halogen.

First claim

The invention claimed is:

1. 3-Acylbenzamide of formula (I)

in which the symbols and indices are defined as follows:
R x represents (C 1 -C 6 )-alkyl,
X represents halogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, R 1 O, R 2 S(O) n or R 1 O—(C 1 -C 6 )-alkyl,
Y represents halogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl or R 1 O, R 2 S(O) n ,
Z represents (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-C(O), (C 1 -C 6 )-alkyl-C(O)—(C 1 -C 6 )-alkyl, phenyl or heterocyclyl, where the radicals phenyl, heterocyclyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl and (C 3 -C 6 )-cycloalkyl each carry m substituents R 3 ,
R 1 represents (C 1 -C 6 )-alkyl or halo-(C 1 -C 6 )-alkyl,
R 2 represents (C 1 -C 6 )-alkyl,
R 3 represents halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-alkyl-O—C(O), cyano or halo-(C 1 -C 6 )-alkyl,
m represents 0, 1, 2, 3 or 4,
n represents 0, 1 or 2.

2. 3-Acylbenzamide according to claim 1 in which
R x represents (C 1 -C 6 )-alkyl,
X represents halogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, R 1 O, R 2 S(O) n or R 1 O—(C 1 -C 6 )-alkyl,
Y represents halogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl or R 1 O, R 2 S(O) n ,
Z represents (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-C(O), (C 1 -C 6 )-alkyl-C(O)—(C 1 -C 6 )-alkyl or phenyl, where the radicals phenyl, (C 2 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl and (C 3 -C 6 )-cycloalkyl each carry m substituents R 3 ,
R 1 represents (C 1 -C 6 )-alkyl or halo-(C 1 -C 6 )-alkyl,
R 2 represents (C 1 -C 6 )-alkyl,
R 3 represents halogen, (C 1 -C 6 )-alkyl, (C 1 -C 3 )-alkyl-O—C(O), cyano or halo-(C 1 -C 6 )-alkyl,
m represents 0, 1, 2, 3 or 4,
n represents 0, 1 or 2.

3. 3-Acylbenzamide according to claim 1 in which
R x represents (C 1 -C 6 )-alkyl,
X represents fluorine, chlorine, bromine, iodine, methyl, ethyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxymethyl, methoxy, methylsulfanyl, methylsulfinyl, methyl sulfonyl, ethylsulfanyl or ethyl sulfonyl,
Y represents chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, methylsulfanyl, methylsulfinyl, methyl sulfonyl or ethyl sulfonyl,
Z represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, tert-butyl, methoxymethyl, chloromethyl, acetyl, vinyl, 1-methylvinyl, 2-methylvinyl, (1,2-dimethyl)vinyl, (2,2-dimethyl)vinyl, 1-methylcyclopropyl, 2-methylcyclopropyl, (2,2-dimethyl)cyclopropyl, (1,2-dimethyl)cyclopropyl, 2-fluorocyclopropyl, (2,2-difluoro)cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 2-thienyl, 2-furyl, phenyl, 4-methoxyphenyl, 4-chlorophenyl, (3-trifluoromethyl)phenyl, 3,5-difluorophenyl, trifluoromethyl or difluoromethyl.

4. Herbicidal composition comprising at least one compound according to claim 1 mixed with one or more formulation auxiliaries.

5. Herbicidal composition according to claim 4 , comprising at least one further pesticidally active substance selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.

6. Method for controlling one or more unwanted plants, comprising applying an effective amount of at least one compound of the formula (I) according to claim 1 or a herbicidal composition thereof to the plants or a site of unwanted vegetation.

7. A product comprising one or more compounds of the formula (I) according to claim 1 or a herbicidal composition thereof for controlling one or more unwanted plants.

8. Product according to claim 7 wherein the compound of the formula (I) is used for controlling said unwanted plants in one or more crops of useful plants.

9. Product according to claim 8 , wherein the useful plants are transgenic useful plants.

10. 3-Acylbenzamide according to claim 3 wherein R x represents methyl.

11. 3-Acylbenzamide according to claim 3 wherein X represents methyl.

12. 3-Acylbenzamide according to claim 3 wherein Y represents methyl sulfonyl.

13. 3-Acylbenzamide according to claim 3 wherein Z represents cyclopropyl.

Assignees

• Bayer Ag

Inventors

• Waldraff Christian
• Koehn Arnim
• Ahrens Hartmut
• Braun Ralf
• Dietrich Hansjoerg
• Machettira Anu Bheemaiah
• Rosinger Christopher Hugh
• Gatzweiler Elmar
• Asmus Elisabeth

Classifications

• C07C65/40

  containing singly bound oxygen-containing groups · CPC title

• C07C2601/08

  the ring being saturated · CPC title

• C07C2601/04

  with a four-membered ring · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title