N-(oxazol-2-yl)-aryl-carboxylic acid amides and use thereof as herbicides

Patent metadata

Field	Value
Publication number	US-9758494-B2
Application number	US-201314647902-A
Country	US
Kind code	B2
Filing date	Dec 3, 2013
Priority date	Dec 6, 2012
Publication date	Sep 12, 2017
Grant date	Sep 12, 2017

Abstract

N-(Oxazol-2-yl)-aryl-carboxylic acid amides and use thereof as herbicides N-(Isoxazol-3-yl)arylcarboxamides and their use as herbicides are described.

In this formula (I), A represents N or C—Y. R, R′, V, X, Y and Z represent radicals such as hydrogen, halogen and organic radicals such as substituted alkyl.

First claim

The invention claimed is:

1. An N-(oxazol-2-yl)arylcarboxamide of formula (I) and/or a salt thereof

in which
A represents CY,
X represents nitro, halogen, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, OR 2 , S(O) n R 2 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , or (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 ,
Y represents hydrogen, nitro, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, OR 1 , S(O) n R 2 , SO 2 N(R 1 ) 2 , N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , or (C 1 -C 6 )-alkylphenyl, where the (C 1 -C 6 )-alkylphenyl radical is substituted by s radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n —(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl and cyanomethyl,
Z represents halogen, cyano, nitro, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, or S(O) n R 2 , or Z optionally represents hydrogen if Y represents S(O) n R 2 ,
V represents hydrogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-halo-alkoxy, S(O) n —(C 1 -C 6 )-alkyl, S(O) n —(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl, halogen, nitro or cyano,
R and R′ independently of one another each represent hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, cyano-(C 1 -C 6 )-alkyl, cyano, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, halogen, amino, or methoxymethyl, with the proviso that at least one of R and/or R′ is hydrogen,
R 1 represents hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-O-(C 1 -C 6 )-alkyl, phenyl, or phenyl-(C 1 -C 6 )-alkyl, where the radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl,
R 2 represents (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl that are each substituted by s radicals from the group consisting of halogen and OR 3 ,
R 3 represents hydrogen or (C 1 -C 6 )-alkyl,
R 4 represents (C 1 -C 6 )-alkyl,
n represents 0, 1 or 2, and
s represents 0, 1, 2 or 3.

2. A herbicidal composition comprising a herbicidally active content of at least one compound of the formula (I) and/or salt as claimed in claim 1 and one or more formulation auxiliaries.

3. A method for controlling unwanted plants, comprising applying an effective amount of at least one compound of formula (I) and/or salt as claimed in claim 1 to the plants and/or to a site of unwanted plants.

4. A method as claimed in claim 3 , comprising controlling one or more unwanted plants in crops of useful plants.

5. A method as claimed in claim 4 , wherein the useful plants are transgenic useful plants.

6. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which Y is other than hydrogen.

7. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which V is other than hydrogen.

8. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which one of R and/or R′ is other than hydrogen.

9. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which one of R and/or R′ is other than hydrogen or (C 1 -C 6 )-alkyl.

10. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which X is other than (C 1 -C 6 )-alkyl.

11. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which Y is other than (C 1 -C 6 )-alkyl.

12. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which R, R′ and V are hydrogen.

13. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which one of R and R′ is hydrogen and the other is not hydrogen, and V is hydrogen.

14. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which
A represents CY,
X represents nitro, halogen, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (OR 2 , S(O) n R 2 , (C 1 -C 6 )-alkyl-S(O) n R 2 , or (C 1 -C 6 )-alkyl-OR 1 ,
Y represents hydrogen, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, OR 1 , S(O) n R 2 , N(R 1 ) 2 , or (C 1 -C 6 )-alkyl-OR 1 ,
Z represents halogen, cyano, nitro, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkyl, or S(O) n R 2 , or Z optionally represents hydrogen if Y represents S(O) n R 2 ,
V represents hydrogen or halogen,
R and R′ independently of one another each represent hydrogen or (C 1 -C 6 )-alkyl, with the proviso that at least one of R and/or R′ is hydrogen,
R 1 represents hydrogen, (C 1 -C 6 )-alkyl, or (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, where the radicals are substituted by s radicals selected from the group consisting of cyano, halogen, OR 3 , and CON(R 3 ) 2 ,
R 2 represents (C 1 -C 6 )-alkyl,
R 3 represents hydrogen or (C 1 -C 6 )-alkyl,
n represents 0, 1 or 2, and
s represents 0 or 1.

15. The N-(oxazol-2-yl)arylcarboxamide and/or salt as claimed in claim 1 in which
A represents CY,
X represents halogen or (C 1 -C 6 )-alkyl,
Y represents S(O) n R 2 or (C 1 -C 6 )-alkyl-OR 1 ,
Z represents halogen, halo-(C 1 -C 6 )-alkyl, or S(O) n R 2 ,
V represents hydrogen,
R and R′ each represent hydrogen,
R 1 represents (C 1 -C 6 )-alkyl substituted by s halogen radicals,
R 2 represents (C 1 -C 6 )-alkyl,
n represents 0, 1 or 2, and
s represents 0 or 1.

Assignees

• Bayer Cropscience Ag

Inventors

• Koehn Arnim
• Ahrens Hartmut
• Braun Ralf
• Heinemann Ines
• Tiebes Joerg
• Waldraff Christian
• Dietrich Hansjoerg
• Gatzweiler Elmar
• Rosinger Christopher Hugh
• Schmutzler Dirk

Classifications

• C07D413/12 Primary

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

• A01N43/56

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title

• C07D263/48 Primary

  Nitrogen atoms not forming part of a nitro radical · CPC title

• A01N41/02

  containing a sulfur-to-oxygen double bond · CPC title

• A01N43/42

  condensed with carbocyclic rings · CPC title