Furancarboxamides

1. A furancarboxamide of formula (I)

in which

R 1 represents fluorine,

m represents 0, 1, or 2,

R represents one of the groups

R 2 represents halogen, cyano, nitro, C 1 –C 8 -alkyl, C 1 –C 8 -alkoxy, C 1 –C 8 -alkythio, C 1 –C 6 -haloalkyl, C 1 –C 6 -haloalkoxy or C 1 –C 6 -haloalkylthio, each halo-containing group having 1 to 13 fluorine, chlorine, and/or bromine atoms,

R 3 and R 4 independently of one another represent halogen, cyano, nitro, C 1 –C 8 -alkyl, C 1 –C 8 -alkoxy, C 1 –C 8 -alkylthio, C 1 –C 6 -haloalkyl, C 1 –C 6 -haloalkoxy, or C 1 –C 6 -haloalkylthio, each halo-containing group having 1 to 13 fluorine, chlorine, and/or bromine atoms,

n represents 3, 4, or 5, and

R 5 represents identical or different radicals selected from the group consisting of halogen, cyano, nitro, C 1 –C 8 -alkyl, C 1 –C 8 -alkoxy, C 1 –C 8 -alkylthio, C 1 –C 6 -halo-alkyl, C 1 –C 6 -haloalkoxy, or C 1 –C 6 -haloalkylthio, each halo-containing group having 1 to 13 fluorine, chlorine, and/or bromine atoms.

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

R 1 represents fluorine,

m represents 0, 1, or 2,

R represents one of the groups

R 2 represents fluorine, chlorine, bromine, iodine, cyano, C 1 –C 6 -alkyl, C 1 –C 6 -alkoxy, C 1 –C 6 -alkylthio, C 1 –C 4 -haloalkyl, C 1 –C 4 -haloalkoxy, or C 1 –C 4 -haloalkyl-thio, each halo-containing group having 1 to 9 fluorine, chlorine, and/or bromine atoms,

R 3 and R 4 independently of one another represent fluorine, chlorine, bromine, iodine, C 1 –C 6 -alkyl, C 1 –C 6 -alkoxy, C 1 –C 6 -alkylthio, C 1 –C 4 -haloalkyl, C 1 –C 4 -haloalkoxy, or C 1 –C 4 -haloalkylthio, each halo-containing group having 1 to 9 fluorine, chlorine, and/or bromine atoms,

n represents 3, 4, or 5, and

R 5 represents identical or different radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, C 1 –C 6 -alkyl, C 1 –C 6 -alkoxy, C 1 –C 6 -alkylthio, C 1 –C 4 -haloalkyl, C 1 –C 4 -haloalkoxy, and C 1 –C 4 -haloalkylthio, each halo-containing group having 1 to 9 fluorine, chlorine, and/or bromine atoms.

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

R 1 represents fluorine,

m represents 0 or 1,

R represents one of the groups

R 2 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoro-methoxy, trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio,

R 3 and R 4 independently of one another represent fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio,

n represents 3 or 4, and

R 5 represents identical or different radicals selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, and difluorochloromethylthio.

4. A furancarboxamide of formula (I) according to claim 1 in which

R 1 represents fluorine,

m represents 0 or 1,

R represents one of the groups

R 2 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, or trifluoromethylthio,

R 3 and R 4 independently of one another represent fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, or trifluoromethylthio,

n represents 3, and

R 5 represents identical or different radicals selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, and trifluoromethylthio.

5. A furancarboxamide of formula (I) according to claim 1 in which

R 1 represents fluorine,

m represents 0 or 1,

R represents one of the groups

R 2 represents fluorine, chlorine, bromine, cyano, t-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy, or trifluoromethylthio,

R 3 and R 4 independently of one anther represent fluorine, chlorine, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, or trifluoromethylthio, and

R 5 represents identical or different radicals selected from the group consisting of fluorine, chlorine, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, and trifluoromethylthio.

6. A furancarboxamide according to claim 1 of formula (I-a)

in which

R 1 represents fluorine,

m represents 0 or 1, and

R 2 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio.

7. A furancarboxamide according to claim 1 of formula (I-b)

in which

R 1 represents fluorine,

m represents 0 or 1, and

R 2 represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio.

8. A furancarboxamide according to claim 1 of formula (I-c)

in which

R 1 represents fluorine,

m represents 0 or 1, and

R 2 represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio.

9. A furancarboxamide according to claim 1 of formula (I-d)

in which

R 1 represents fluorine,

m represents 0 or 1, and

R 3 and R 4 independently of one another represent fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio.

10. A furancarboxamide according to claim 1 of formula (I-e)

in which

R 1 represents fluorine,

m represents 0 or 1, and

R 2 represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio.

11. A furancarboxamide according to claim 1 of formula (I-f)

in which

R 1 represents fluorine,

m represents 0 or 1, and

R 3 and R 4 independently of one another represent fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio.

12. A process for preparing furancarboxamides of formula (I) according to claim 1 comprising

(a) reacting a carboxylic acid derivative of formula (II)

 in which G represents halogen, hydroxyl, or C 1 –C 6 -alkoxy, with an aniline derivative of formula (III)

 in which R, R 1 , and m are as defined for formula (I) in claim 1 , optionally in the presence of a catalyst, optionally in the presence of an acid binder, and optionally in the presence of a diluent, or

(b) reacting a carboxamide derivative of formula (IV)

 in which R 1 and m are as defined for formula (I) in claim 1 , with a boronic acid derivative of formula (V)

 in which

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

G 1 and G 2 each represent hydrogen or together represent tetramethylethylene,

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

(c) reacting a carboxamide boronic acid derivative of formula (VI)

 in which

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

G 1 and G 2 each represent hydrogen or together represent tetramethylethylene

 with a phenyl derivative of formula (VII)

 in which R is 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, or

(d) reacting a carboxamide derivative of formula (IV)

 in which R 1 and m are as defined for formula (I) in claim 1 , with a phenyl derivative of formula (VII)

 in which R is as defined for formula (I) in claim 1 , in the presence of a palladium or platinum catalyst, in the presence of 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane, optionally in the presence of an acid binder, and optionally in the presence of a diluent.

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

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

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