Difluoromethyl thiazolyl carboxanilides
View Patent ↗The present invention relates to novel difluoromethylthiazolylcarboxanilides of the formula (I) in which R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the disclosure, to a plurality of processes for preparing these substances and their use for controlling unwanted microorganisms, and to novel intermediates and their preparation.
1. A difluoromethylthiazolylcarboxanilide of 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 -alkylthio, C 1 -C 4 -alkylsulphonyl, 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 -haloalkylsulphonyl having in each case 1 to 5 halogen atoms, with the proviso that R 1 , R 2 , R 3 , R 4 , and R 5 do not simultaneously represent hydrogen, or
R 1 and R 2 together or R 2 and R 3 together optionally also represent optionally halogen- or C 1 -C 6 -alkyl-substituted alkenylene.
2. A difluoromethylthiazolylcarboxanilide of formula (I) according to 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 i-propyl, n-, i-, s-, or t-butyl, methoxy, ethoxy, methylthio, ethylthio, n- or i-propylthio, cyclopropyl, trifluoro-methyl, trichloromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloro-methylthio, or trifluoromethylthio, with the proviso that R 1 , R 2 , R 3 , R 4 , and R 5 do not simultaneously represent hydrogen, or
R 1 and R 2 together or R 2 and R 3 together optionally also represent optionally fluorine-, chlorine-, bromine-, or methyl-substituted butadienylene.
3. A difluoromethylthiazolylcarboxanilide of formula (I) according to claim 1 in which R 1 , R 2 , R 3 , R 4 , and R 5 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, methoxy, methylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, or trifluoromethylthio, with the proviso that R 1 , R 2 , R 3 , R 4 , and R 5 do not simultaneously represent hydrogen.
4. A difluoromethylthiazolylcarboxanilide of formula (I) according to claim 1 in which
R 1 , R 2 , R 4 , and R 5 each represent hydrogen, and
R 3 represents halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphonyl, or C 3 -C 6 -cycloalkyl, or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkylsulphonyl having in each case 1 to 5 halogen atoms.
5. A difluoromethylthiazolylcarboxanilide of formula (I) according to claim 1 in which
R 1 , R 2 , R 4 , and R 5 each represent hydrogen, and
R 3 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoro-methoxy, or trifluoromethylthio.
6. A difluoromethylthiazolylcarboxanilide of formula (I) according to 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 halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphonyl, 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 -haloalkylsulphonyl having in each case 1 to 5 halogen atoms.
7. A difluoromethylthiazolylcarboxanilide of formula (I) according to 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 fluorine, chlorine, bromine, methyl, or trifluoromethyl.
8. A difluoromethylthiazolylcarboxanilide of formula (I) according to 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 halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphonyl, 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 -haloalkylsulphonyl having in each case 1 to 5 halogen atoms.
9. A difluoromethylthiazolylcarboxanilide of formula (I) according to 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 fluorine, chlorine, bromine, methyl, or trifluoromethyl.
10. A difluoromethylthiazolylcarboxanilide of formula (I) according to 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 halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphonyl, 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 -haloalkylsulphonyl having in each case 1 to 5 halogen atoms.
11. A difluoromethylthiazolylcarboxanilide of formula (I) according to 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 fluorine, chlorine, bromine, methyl, or trifluoromethyl.
12. A difluoromethylthiazolylcarboxanilide of formula (I) according to claim 1 in which R 5 represents hydrogen.
13. A composition for controlling unwanted microorganisms comprising one or more thiazolylcarboxanilides of formula (I) according to claim 1 and one or more extenders and/or surfactants.