Method for producing carboxamides

1. A process for preparing a carboxamide of formula (I)

in which

R is C 3 -C 12 -cycloalkyl, C 3 -C 12 -cycloalkenyl, C 6 -C 12 -bicycloalkyl, C 2 -C 12 -oxacycloalkyl, C 4 -C 12 -oxacycloalkenyl, C 3 -C 12 -thiacycloalkyl, C 4 -C 12 -thiacycloalkenyl, C 2 -C 12 -azacycloalkyl, each of which may optionally be mono- or polysubstituted identically or differently by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen and/or cyano,

or phenyl which is optionally mono- to pentasubstituted identically or differently, where the substituents are each selected from the list W l ,

or unsubstituted C 2 -C 20 -alkyl,

or C 1 -C 20 -alkyl which is mono- or polysubstituted identically or differently by halogen, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -haloalkylthio, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -haloalkylsulfonyl, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkylamino, halo-di (C 1 -C 6 -alkyl)amino, -SiR 1 R 2 R 3 and/or C 3 -C 6 -cycloalkyl, where the cycloalkyl moiety may in turn optionally be mono- to tetrasubstituted identically or differently by halogen, C 1 -C 20 -alkyl and/or C 1 -C 4 -haloalkyl,

W 1 is halogen, cyano, nitro, amino, hydroxyl, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkyl-thio, C 1 -C 8 -alkylsulfinyl, C 1 -C 8 -alkylsulfonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy; C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkylthio, C 1 -C 6 -haloalkylsulfinyl or C 1 -C 6 -haloalkylsulfonyl having in each case from 1 to 13 identical or different halogen atoms; C 2 -C 6 -haloalkenyl or C 2 -C 6 -haloalkenyloxy having in each case from 1 to 11 identical or different halogen atoms; C 3 -C 6 -cycloalkyl or C 3 -C 6 -cyclo-alkyloxy;

R l and R 2 are each independently hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl or C 1 -C 6 -haloalkyl,

R 3 is hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-thio -C 1 -C 4 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -cycloalkyl, or in each case optionally substituted phenol or phenylalkyl,

said process comprising

reacting 5-fluoro- 1,3-dimethyl-1H-pyrazole-4-carbonyl fluoride of formula (II)

 with aniline derivatives of formula (III)

 in which R is as defined above,

in the presence of an acid acceptor of formula (IV)

 in which R 4 and R 5 are each independently C 1 -C 3 -alkyl.

2. The process as claimed in claim 1 , wherein the acid acceptor used is 2-methylpyridine, 2,3-dimethylpyridine, 2-methyl-5-ethylpyridine, 2,6-dimethylpyridine, 2,4-dimethylpyridine, 3,4-dimethylpyridine, and/or 2,4,6-trimethylpyridine.

3. The process as claimed in claim 1 , wherein a temperature of from 100 to 150° C. is employed.

4. The process as claimed in claim 1 , wherein an aniline derivative of formula (III-1)

is used.

5. The process as claimed in claim 1 , wherein 2-(1,3-dimethylbutyl)-phenylamine is used as the aniline derivative of the formula (III).

6. The process as claimed in claim 2 , wherein a temperature of from 100 to 150° C. is employed.

7. The process as claimed in claim 2 , wherein an aniline derivative of formula (III-1)

is used.

8. The process as claimed in claim 3 , wherein an aniline derivative of formula (III-1)

is used.

9. The process as claimed in claim 2 , wherein 2-(1,3-dimethylbutyl)-phenylamine is used as the aniline derivative of the formula (III).

10. The process as claimed in claim 3 , wherein 2-(1,3-dimethylbutyl)-phenylamine is used as the aniline derivative of the formula (III).

11. The process as claimed in claim 4 , wherein 2-(1,3-dimethylbutyl)-phenylamine is used as the aniline derivative of the formula (III).