N-(isoxazol-3-yl)-aryl-carboxylic acid amides and use thereof as herbicides

Patent metadata

Field	Value
Publication number	US-9732048-B2
Application number	US-201314648032-A
Country	US
Kind code	B2
Filing date	Dec 3, 2013
Priority date	Dec 7, 2012
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

The invention relates to N-(isoxazol-3-yl)-aryl-carboxylic acid amides and use thereof as herbicides. In formula (I), A stands for N or C—Y. R, V, X, Y, and Z stand for groups such as hydrogen, halogen, and organic groups such as substituted alkyl.

First claim

The invention claimed is:

1. The N-(isoxazol-3-yl)arylcarboxamide and/or salt of formula (1)

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 S(O) n R 2 ,
Z represents halogen, cyano, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n R 2 , or hydrogen,
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 represents hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, cyano-(C 1 -C 6 )-alkyl, cyano, methylsulfenyl, methyl-sulfinyl, methylsulfonyl, acetylamino, halogen, amino, or methoxymethyl,
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, phenyl-(C 1 -C 6 )-alkyl, where the 8 last-mentioned 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 selected 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 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 formula (I) as claimed in claim 1 and one more formulation auxiliaries.

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

4. A method as claimed in claim 3 , wherein the compound of formula (I) controls 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. An N-(isoxazol-3-yl)arylcarboxamide of formula (I) and/or a salt thereof as claimed in claim 1 , wherein R is other than hydrogen.

7. An N-(isoxazol-3-yl)arylcarboxamide of formula (I) and/or a salt thereof as claimed in claim 1 , wherein Z represents cyano, nitro, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, S(O) n R 2 , or hydrogen.

8. An N-(isoxazol-3-yl)arylcarboxamide of formula (I) and/or a salt thereof as claimed in claim 1 , wherein X represents 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 .

9. An N-(isoxazol-3-yl)arylcarboxamide of formula (I) and/or a salt thereof as claimed in claim 1 , wherein R represents (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, cyano-(C 1 -C 6 )-alkyl, cyano, methylsulfenyl, methyl-sulfinyl, methylsulfonyl, acetylamino, halogen, amino, or methoxymethyl.

10. An N-(isoxazol-3-yl)arylcarboxamide of formula (I) and/or a salt thereof as claimed in claim 1 , wherein R represents (C 1 -C 6 )-alkyl.

11. An N-(isoxazol-3-yl)arylcarboxamide of formula (I) and/or a salt thereof as claimed in claim 1 , wherein
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 , or (C 1 -C 6 )-alkyl-OR 1 ,
Y S(O) n R 2 ,
Z represents halogen, cyano, nitro, (C 1 -C 6 )-alkyl, (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,
R represents hydrogen, (C 1 -C 6 )-alkyl, (halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, cyano-(C 1 -C 6 )-alkyl, cyano, or halogen,
R 1 represents hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, where the 3 last-mentioned radicals are substituted by s radicals selected from the group consisting of cyano, halogen, and OR 3 ,
R 2 represents (C 1 -C 6 )-alkyl that is substituted by s radicals selected 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 1 or 2, and
s represents 0 or 1.

12. An N-(isoxazol-3-yl)arylcarboxamide of formula (I) and/or a salt thereof as claimed in claim 1 , wherein
A represents CY,
X represents (C 1 -C 6 )-alkyl,
Y S(O) n R 2 ,
Z represents halo-(C 1 -C 6 )-alkyl or S(O) n R 2 ,
V represents hydrogen,
R represents hydrogen, (C 1 -C 6 )-alkyl, or halogen,
R 2 represents (C 1 -C 6 )-alkyl,
n represents 1 or 2, and
s represents 0.

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

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

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title

• C07D261/14 Primary

  Nitrogen atoms · CPC title