Methylthiophene carboxanilides

1. A methylthiophenecarboxanilide of formula (I)

in which

R 1 and R 2 are identical or different and independently of one another represent hydrogen or fluorine,

R 3 , R 4 , and R 6 are identical or different and independently of one another represent hydrogen, halogen, C 1 -C 6 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,

R 5 represents hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, C 1 -C 4 -haloalkoxy having 1 to 5 halogen atoms, C 1 -C 4 -haloalkylthio having 1 to 5 halogen atoms, or C 1 -C 4 -haloalkylsulfonyl having 1 to 5 halogen atoms,

with the proviso that R 3 , R 4 , R 5 , and R 6 do not simultaneously represent hydrogen.

2. A methylthiophenecarboxanilide of formula (I) according to claim 1 in which

R 1 and R 2 are identical or different and independently of one another represent hydrogen or fluorine,

R 3 , R 4 , and R 6 are identical or different and independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, trifluoromethyl, trichloromethyl, or trifluoroethyl,

R 5 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, cyclopropyl, methoxy, ethoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, or trifluoromethylthio,

with the proviso that R 3 , R 4 , R 5 , and R 6 do not simultaneously represent hydrogen.

3. A methylthiophenecarboxanilide of formula (I) according to claim 1 in which

R 1 and R 2 are identical or different and independently of one another represent hydrogen or fluorine,

R 3 , R 4 , and R 6 are identical or different and independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, or trifluoromethyl,

R 5 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, cyclopropyl, methoxy, methylthio, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, or trifluoromethylthio,

with the proviso that R 3 , R 4 , R 5 , and R 6 do not simultaneously represent hydrogen.

4. A process for preparing a methylthiophenecarboxanilide of formula (I) according to claim 1 comprising

(a) reacting a methylthiophenecarbonyl halide of formula (II)

in which X 1 represents halogen,

 with an aniline derivative of formula (III)

in which R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are as defined for formula (I) in claim 1 ,

 optionally in the presence of an acid binder and optionally in the presence of a diluent, or

(b) reacting a methylthiophenecarboxhalogenanilide of formula (IV)

in which

R 1 and R 2 are as defined for formula (I) in claim 1 , and

X 2 represents bromine or iodine, with a boronic acid of formula (V)

in which R 3 , R 4 , R 5 , and R 6 are as defined for formula (I) in claim 1 , in the presence of a catalyst, optionally in the presence of an acid binder, and optionally in the presence of a diluent.

5. A composition for controlling unwanted micro-organisms comprising one or more methylthiophenecarboxanilides of formula (I) according to claim 1 and one or more extenders and/or surfactants.

6. A method for controlling unwanted micro-organisms comprising applying an effective amount of a methylthiophenecarboxanilide of formula (I) according to claim 1 to the micro-organisms and/or their habitat.

7. A method for preparing compositions for controlling unwanted micro-organisms comprising mixing one or more methylthiophenecarboxanilides of formula (I) according to claim 1 with one or more extenders and/or surfactants.