Thiazolyl biphenyl amides

1. A thiazolylbiphenylamide of the formula (I)

in which

R 1 , R 2 , R 3 , R 4 , and R 5 independently of one another represent hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylsulfonyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkylsulfonyl having in each case 1 to 5 halogen atoms,

R 6 represents C 1 -C 8 -alkyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl; represents C 1 -C 6 -haloalkyl, C 1 -C 4 -haloalkyl-sulfanyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; or represents —CH 2 NR 10 R 11 , and

R 10 and R 11 independently of one another represent hydrogen, C 1 -C 8 -alkyl, or C 3 -C 8 -cycloalkyl; or represent C 1 -C 8 -haloalkyl or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms.

2. A thiazolylbiphenylamide of formula (I) as claimed in claim 1 in which

R 1 , R 2 , R 3 , R 4 , and R 5 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or isopropyl, n-, iso-, sec-, or tert-butyl, methoxy, ethoxy, methylthio, ethylthio, n- or isopropylthio, cyclopropyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, or trifluoromethylthio,

R 6 represents C 1 -C 6 -alkyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, or C 3 -C 6 -cycloalkyl; represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkyl-sulfanyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms, or represents —CH 2 NR 10 R 11 , and

R 10 and R 11 independently of one another represent hydrogen, C 1 -C 6 -alkyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl or C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms.

3. A thiazolylbiphenylamide of formula (I) as claimed in claim 1 in which

R 1 , R 2 , R 3 , R 4 , and R 5 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, methyl, methoxy, methylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, or trifluoromethylthio,

R 6 represents methyl, ethyl, n- or isopropyl, n-, iso-, sec-, or tert-butyl, pentyl, or hexyl, methylsulfinyl, ethylsulfinyl, n- or isopropylsulfinyl, n-, iso-, sec-, or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, sec-, or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylsulfanyl, difluorochloromethylsulfanyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl, or —CH 2 NR 10 R 11 , and

R 10 and R 11 independently of one another represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec-, or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, or trifluoromethoxymethyl.

4. A thiazolylbiphenylamide of formula (I) as claimed in claim 1 in which four of the radicals R 1 , R 2 , R 3 , R 4 , and R 5 represent hydrogen.

5. A thiazolylbiphenylamide of formula (I) as claimed in claim 1 in which

R 1 , R 2 , R 4 , and R 5 each represent hydrogen, and

R 3 represents hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylsulfonyl, or C 3 -C 6 -cycloalkyl; or represents C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkyl-sulfonyl having in each case 1 to 5 halogen atoms.

6. A thiazolylbiphenylamide of formula (I) as claimed in claim 1 in which

R 2 , R 4 , and R 5 each represent hydrogen, and

R 1 and R 3 independently of one another represent hydrogen, halogen, cyano, nitro, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfonyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkylsulfonyl having in each case 1 to 5 halogen atoms.

7. A thiazolylbiphenylamide of formula (I) as claimed in claim 1 in which

R 1 , R 4 , and R 5 each represent hydrogen, and

R 2 and R 3 independently of one another represent hydrogen, halogen, cyano, nitro, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfonyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkylsulfonyl having in each case 1 to 5 halogen atoms.

8. A thiazolylbiphenylamide of formula (I) as claimed in claim 1 in which

R 1 , R 3 , and R 5 each represent hydrogen, and

R 2 and R 4 independently of one another represent hydrogen, halogen, cyano, nitro, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfonyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkylsulfonyl having in each case 1 to 5 halogen atoms.

9. A thiazolylbiphenylamide of formula (I) as claimed in claim 1 in which R 6 represents methyl, ethyl, n- or isopropyl, n-, iso-, sec-, or tert-butyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, or trifluoromethoxymethyl.

10. A process for preparing a thiazollylbiphenylamide of formula (I) as claimed in claim 1 comprising reacting a thiazolylbiphenylamide of formula (II)

in which R 1 , R 2 , R 3 , R 4 , and R 5 are as defined for formula (I) in claim 1 , with a halide of formula (III)

R 6 —X  (III)

in which

R 6 is as defined for formula (I) in claim 1 , and

X represents chlorine, bromine, or iodine,

in the presence of a base and in the presence of a diluent.

11. A composition for controlling unwanted phytopathogenic fungi comprising one or more thiazolylbiphenylamides of formula (I) as claimed in claim 1 and one or more extenders and/or surfactants.

12. A method of controlling unwanted phytopathogenic fungi comprising applying an effective amount of one or more thiazolylbiphenylamides of formula (I) according to claim 1 to the fungi and/or their habitat.

13. A process for preparing compositions for controlling unwanted phytopathogenic fungi comprising mixing one or more thiazolylbiphenylamide of formula (I) as claimed in claim 1 with one or more extenders and/or surfactants.