Thiazol-(bi)cycloalkyl-carboxanilides
View Patent ↗This invention relates to novel thiazole(bi)cycloalkylcarboxanilides of the formula (I) in which Q and R 1 are as defined in the disclosure, to a process for preparing these compounds and to their use for controlling unwanted microorganisms.
1. A thiazole(bi)cycloalkylcarboxanilide of formula (I)
in which
Q represents a group
R 1 represents hydrogen, 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, or C 3 -C 8 -cycloalkyl; represents C 1 -C 6 -haloalkyl, C 1 -C 4 -haloalkylsulfanyl, 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 —COR 7 , —CONR 8 R 9 , or —CH 2 NR 10 R 11 ,
R 2 represents C 3 -C 12 -cycloalkyl, or C 6 -C 12 -bicycloalkyl, each of which is is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano, hydroxyl, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 6 -haloalkyl having 1 to 9 fluorine, chlorine, and/or bromine atoms, and C 1 -C 6 -haloalkoxy having 1 to 9 fluorine, chlorine, and/or bromine atoms,
R 3 represents fluorine, chlorine, bromine, or methyl,
m represents 0, 1, 2, 3, or 4,
R 7 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl; represents C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, 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 4-(difluoromethyl)-2-methyl-1,3-thiazol-2-yl,
R 8 and R 9 independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl; or represents C 1 -C 8 -haloalkyl, 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
R 8 and R 9 together with the nitrogen atom to which they are attached form a saturated heterocycle that is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl and that has 5 to 8 ring atoms, where the heterocycle optionally contains 1 or 2 further nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur, and NR 13 ,
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, or
R 10 and R 11 together with the nitrogen atom to which they are attached form a saturated heterocycle that is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl and that has 5 to 8 ring atoms, where the heterocycle optionally contains 1 or 2 further nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur, and NR 13 , and
R 13 represents hydrogen or C 1 -C 6 -alkyl.
2. A thiazole(bi)cycloalkylcarboxanilide of formula (I) according to claim 1 in which
Q represents a group
R 1 represents hydrogen; 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 -haloalkylsulfanyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, or C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; or represents —COR 7 , —CONR 8 R 9 , or —CH 2 NR 10 R 11 ,
R 2 represents C 3 -C 12 -cycloalkyl, or C 6 -C 12 -bicycloalkyl, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkyl having 1 to 9 fluorine, chlorine, and/or bromine atoms, and C 1 -C 4 -haloalkoxy having 1 to 9 fluorine, chlorine, and/or bromine atoms,
R 3 represents fluorine, bromine or methyl,
m represents 0, 1, 2, or 3,
R 7 represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, 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 -haloalkoxy, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, or C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; or represents 4-(difluoromethyl)-2-methyl-1,3-thiazol-2-yl,
R 8 and R 9 independently of one another represent hydrogen, C 1 -C 6 -alkyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, or C 3 -C 6 -cycloalkyl; or represents C 1 -C 4 -haloalkyl, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, or C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms, or
R 8 and R 9 together with the nitrogen atom to which they are attached form a saturated heterocycle that is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl and that has 5 to 8 ring atoms, where the heterocycle optionally contains 1 or 2 further nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur, and NR 13 ,
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, or
R 10 and R 11 together with the nitrogen atom to which they are attached form a saturated heterocycle that is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl and which has 5 to 8 ring atoms, where the heterocycle optionally contains 1 or 2 further nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur, and NR 12 , and
R 13 represents hydrogen or C 1 -C 4 -alkyl.
3. A thiazole(bi)cycloalkylcarboxanilide of formula (I) according to claim 1 in which
Q represents a group
R 1 represents hydrogen, 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, or trifluoromethoxymethyl; or represents —COR 7 , —CONR 8 R 9 , or —CH 2 NR 10 R 11 ,
R 2 represents C 3 -C 10 -cycloalkyl, or C 6 -C 10 -bicycloalkyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, hydroxyl, methyl, ethyl, n- or isopropyl, n-, iso-, sec-, or tert-butyl, methoxy, ethoxy, n- or isopropoxy, n-, iso-, sec-, or tert-butoxy, trifluoromethyl, difluoromethyl, trichloromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy, trichloromethoxy, or difluorochloromethoxy,
R 3 represents fluorine, bromine, or methyl,
m represents 0, 1, 2, or 3,
R 7 represents hydrogen, methyl, ethyl, n- or isopropyl, tert-butyl, methoxy, ethoxy, tert-butoxy, cyclopropyl; trifluoromethyl, trifluoromethoxy, or 4-(difluoromethyl)-2-methyl-1,3-thiazol-2-yl,
R 8 and R 9 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, or
R 8 and R 9 together with the nitrogen atom to which they are attached form a saturated heterocycle selected from the group consisting of morpholine, thiomorpholine, and piperazine, each of which is optionally mono- to tetra-substituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, and methyl, where the piperazine is optionally substituted on the second nitrogen atom by R 13 ,
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, or
R 10 and R 11 together with the nitrogen atom to which they are attached form a saturated heterocycle selected from the group consisting of morpholine, thiomorpholine, and piperazine, each of which is optionally mono- to tetra-substituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, and methyl, where the piperazine is optionally substituted on the second nitrogen atom by R 13 , and
R 13 represents hydrogen, methyl, ethyl, n- or isopropyl, or n-, iso-, sec-, or tert-butyl.
4. A thiazole(bi)cycloalkylcarboxanilide of formula (I) according to any of claims 1 , 2 , or 3 in which R 1 is hydrogen.
5. A process for preparing a thiazole(bi)cycloalkylcarboxanilides of formula (I) according to claim 1 comprising
(1) 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)
H 2 N-Q (III)
in which Q is as defined for formula (I) in claim 1 , in the presence of an acid binder and in the presence of a diluent to form a compound of formula (I-a)
in which Q is as defined for formula (I) in claim 1 , and
(2) optionally reacting a compound of formula (I-a) with a halide of the formula (III)
R 1-1 —X (IV)
in which
R 1-1 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, or C 3 -C 8 -cycloalkyl; represents C 1 -C 6 -haloalkyl, C 1 -C 4 -haloalkylsulfanyl, 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 -halo-cycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; or represents —COR 7 , —CONR 8 R 9 , or —CH 2 NR 10 R 11 ,
R 7 , R 8 , R 9 , R 10 , and R 11 are 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.
6. A composition for eliminating or reducing unwanted microorganisms in plants comprising one or more thiazole(bi)cycloalkylcarboxanilides of formula (I) according to claim 1 and one or more extenders and/or surfactants.
7. A method for eliminating or reducing unwanted microorganisms in plants comprising applying an effective amount of one or more thiazole(bi)cycloalkylcarboxanilides of formula (I) according to claim 1 to the microorganisms and/or their habitat.
8. A process for preparing a composition for eliminating or reducing unwanted microorganisms in plants comprising mixing one or more thiazole(bi)cycloalkylcarboxanilides of the formula (I) according to claim 1 with one or more extenders and/or surfactants.