Thiazolylpiperidine Derivatives as Fungicides
Thiazolylpiperidine derivatives of the formula (I), in which the symbols A, G, Y, n, R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given in the description, and also agrochemically active salts thereof, and their use for controlling phytopathogenic harmful fungi, and also processes for preparing compounds of the formula (I).
1 . Compounds of the formula (I),
in which the symbols have the following meanings:
A represents phenyl which may contain up to three substituents,
where the substituents independently of one another are selected from the list below:
cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 4 -C 10 -cycloalkylalkyl, C 4 -C 10 -alkylcycloalkyl, C 5 -C 10 -alkylcycloalkylalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, benzyl, phenyl, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, OCH 2 OCH 3 , SH, C 1 -C 4 -alkylthio, C 1 -C 6 -haloalkylthio, CHO, COOH, (C 1 -C 4 -alkoxy)carbonyl, CONR 3 R 4 , CR 3 ═NOR 4 , (C 1 -C 4 -alkyl)carbonyl, (C 1 -C 4 -haloalkyl)carbonyl, (C 1 -C 4 -alkyl)carbonyloxy, (C 1 -C 4 -alkyl)carbonylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, NR 3 R 4 , NR 3 COR 4 , SF 5 , SO 2 NR 3 R 4 , C 2 -C 4 -alkoxyalkyl, or 1-methoxycyclopropyl,
or
A represents a heteroaromatic radical selected from the group below: furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl,
which may contain up to three substituents, where the substituents independently of one another are selected from the list below:
substituents at carbon:
cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl C 4 -C 10 -cycloalkylalkyl, C 4 -C 10 -alkylcycloalkyl, C 5 -C 10 -alkylcycloalkylalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, tri(C 1 -C 4 -alkyl)silyl, benzyl, phenyl, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, OCH 2 OCH 3 , SH, C 1 -C 4 -alkylthio, C 1 -C 6 -haloalkylthio, CHO, COOH, (C 1 -C 4 -alkoxy)carbonyl, CONR 3 R 4 , CR 3 ═NOR 4 , (C 1 -C 4 -alkyl)carbonyl, (C 1 -C 4 -haloalkyl)carbonyl, (C 1 -C 4 -alkyl)carbonyloxy, (C 1 -C 4 -alkyl)carbonylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, NR 3 R 4 , NR 3 COR 4 , SF S , SO 2 NR 3 R 4 , C 2 -C 4 -alkoxyalkyl or 1-methoxycyclopropyl,
substituents at nitrogen:
hydroxyl, cyano, NR 3 R 4 , C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 4 -C 10 -alkylcycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl or C 2 -C 6 -haloalkynyl,
G represents (C(R 5 ) 2 ) p where p=1 or 2,
or
G represents NH, with the proviso that G is attached to a carbon atom of A,
Y represents sulphur or oxygen,
R 1 represents hydrogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl or halogen,
n=0 to 2,
R 2 represents C 1 -C 8 -alkyl, C 1 -C 4 haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, adamantan-1-yl or adamantan-2-yl,
or
R 2 represents unsubstituted or substituted C 3 -C 10 -cycloalkyl,
where the substituents independently of one another are selected from the list below:
cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, tri(C 1 -C 4 -alkyl)silyl, phenyl, hydroxyl, oxo, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 6 -alkylthio or C 1 -C 6 -haloalkylthio,
or
R 2 represents unsubstituted or substituted C 5 -C 10 -cycloalkenyl,
where the substituents independently of one another are selected from the list below:
cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, tri(C 1 -C 4 -alkyl)silyl, phenyl, hydroxyl, oxo, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 6 -alkylthio or C 1 -C 6 -haloalkylthio,
or
R 2 represents unsubstituted or substituted phenyl,
where the substituents independently of one another are selected from the list below:
cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 4 -C 10 -cycloalkylalkyl, C 4 -C 10 -halocycloalkylalkyl, C 4 -C 10 -alkylcycloalkyl, C 5 -C 10 -alkylcycloalkylalkyl, C 4 -C 10 -cycloalkoxyalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 3 -C 8 -cycloalkenyl, C 3 -C 8 -halocycloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkoxyalkyl, C 2 -C 6 -haloalkoxyalkyl, C 3 -C 8 -alkoxyalkoxyalkyl, tri(C 1 -C 4 -alkyl)silyl, benzyl, phenyl, hydroxyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkoxyalkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -halocycloalkoxy, C 4 -C 10 -cycloalkylalkyloxy, NR 3 R 4 , SH, SF 5 , C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 3 -C 6 -cycloalkylthio, CHO, COOH, (C 1 -C 6 -alkoxy)carbonyl, CONR 3 R 4 , CR 3 ═NOR 4 , (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 6 -haloalkyl)carbonyl, (C 1 -C 6 -alkyl)carbonyloxy, (C 1 -C 6 -haloalkyl)carbonyloxy, (C 1 -C 6 -alkyl)carbonylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -haloalkylsulphonyl, NR 3 COR 4 or SO 2 NR 3 R 4 ,
or
R 2 represents saturated or partially or fully unsaturated unsubstituted or substituted naphthyl or indenyl,
where the substituents independently of one another are selected from the list below:
cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 4 alkyl)silyl, benzyl, phenyl, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 6 -alkylthio or C 1 -C 6 -haloalkylthio,
or
R 2 represents an unsubstituted or substituted 5- or 6-membered heteroaryl radical, where the substituents independently of one another are selected from the list below:
substituents at carbon:
cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 4 -C 10 -cycloalkylalkyl, C 4 -C 10 -alkylcycloalkyl, C 5 -C 10 -alkylcycloalkylalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, benzyl, phenyl, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, OCH 2 OCH 3 , SH, C 1 -C 4 -alkylthio, C 1 -C 6 -haloalkylthio, COOH, (C 1 -C 4 -alkoxy)carbonyl, CONR 3 R 4 , (C 1 -C 4 -alkyl)carbonyl, (C 1 -C 4 -haloalkyl)carbonyl, (C 1 -C 4 -alkyl)carbonyloxy, (C 1 -C 4 -alkyl)carbonylthio, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, NR 3 R 4 , NR 3 COR 4 , SF 5 , SO 2 NR 3 R 4 , C 2 -C 4 -alkoxyalkyl or 1-methoxycyclopropyl,
substituents at nitrogen:
cyano, C 1 -C 6 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 4 -C 10 -alkylcycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl or phenyl,
or
R 2 represents benzo-fused unsubstituted or substituted 5- or 6-membered heteroaryl, where the substituents independently of one another are selected from the list below:
substituents at carbon:
cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl C 4 -C 10 -cycloalkylalkyl, C 4 -C 10 -alkylcycloalkyl, C 5 -C 10 -alkylcycloalkylalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, benzyl, phenyl, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, OCH 2 OCH 3 , SH, C 1 -C 4 -alkylthio, C 1 -C 6 -haloalkylthio, COOH, (C 1 -C 4 -alkoxy)carbonyl, CONR 3 R 4 , (C 1 -C 4 -alkyl)carbonyl, (C 1 -C 4 -haloalkyl)carbonyl, (C 1 -C 4 -alkyl)carbonyloxy, (C 1 -C 4 -alkyl)carbonylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, NR 3 R 4 , NR 3 COR 4 , SF 5 , SO 2 NR 3 R 4 , C 2 -C 4 -alkoxyalkyl or 1-methoxycyclopropyl,
substituents at nitrogen:
cyano, C 1 -C 6 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 4 -C 10 -alkylcycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halo alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl or phenyl,
or
R 2 represents unsubstituted or substituted C 5 -C 15 -heterocyclyl,
where the possible substituents independently of one another are selected from the list below:
substituents at carbon:
cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl C 4 -C 10 -cycloalkylalkyl, C 4 -C 10 -alkylcycloalkyl, C 5 -C 10 -alkylcycloalkylalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, tri(C 1 -C 4 -alkyl)silyl, benzyl, phenyl, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, OCH 2 OCH 3 , SH, C 1 -C 4 -alkylthio, C 1 -C 6 -haloalkylthio, COOH, (C 1 -C 4 -alkoxy)carbonyl, CONR 3 R 4 , (C 1 -C 4 -alkyl)carbonyl, (C 1 -C 4 -haloalkyl)carbonyl, (C 1 -C 4 -alkyl)carbonyloxy, (C 1 -C 4- alkyl)carbonylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, NR 3 R 4 , NR 3 COR 4 , SF 5 , SO 2 NR 3 R 4 , C 2 -C 4 -alkoxyalkyl or 1-methoxycyclopropyl,
substituents at nitrogen:
cyano, C 1 -C 6 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 4 -C 10 -alkylcycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl or phenyl,
R 3 , R 4 independently of one another represent hydrogen, C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C 3 -C 6 -cycloalkyl, benzyl or phenyl,
R 5 are identical or different and independently of one another represent hydrogen, C 1 -C 2 -alkyl or C 1 -C 2 -haloalkyl,
and also agrochemically active salts thereof.
2 . Compounds of the formula (I) according to claim 1
in which the symbols have the meanings below:
A represents phenyl which may contain up to two substituents,
where the substituents independently of one another are selected from the list below:
cyano, halogen, methyl, ethyl, propyl, 1-methylethyl, 1,1-dimethylethyl, CF 3 , CHF 2 , C 2 F 5 , CCl 3 , OMe, OCF 3 , OCHF 2 or OC 2 F 5 ,
or
A represents a heteroaromatic radical selected from the group below: pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl,
which may contain up to two substituents, where the substituents independently of one another are selected from the list below:
substituents at carbon:
cyano, halogen, methyl, ethyl, propyl, 1-methylethyl, 1,1-dimethylethyl, CF 3 , CHF 2 , C 2 F 5 , CCl 3 , OMe, OCF 3 , OCHF 2 or OC 2 F 5 ,
substituents at nitrogen:
methyl, ethyl or CF 3 ,
G represents CH 2 ,
Y represents sulphur or oxygen,
R 1 represents hydrogen,
n=0 bis 2,
R 2 represents methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl, propyl, butyl, pentyl, hexyl, adamantan-1-yl or adamantan-2-yl,
or
R 2 represents C 5 -C 8 -cycloalkyl which may contain up to four substituents,
where the substituents independently of one another are selected from the list below:
methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl,
or
R 2 represents C 5 -C 8 -cycloalkenyl which may contain up to four substituents,
where the substituents independently of one another are selected from the list below:
methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl,
or
R 2 represents phenyl which may contain up to two substituents,
where the substituents independently of one another are selected from the list below:
cyano, nitro, halogen, methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl, CF 3 , CHF 2 , C 2 F 5 , CCl 3 , —CH═CH 2 , —CH 2 CH═CH 2 , benzyl, phenyl, OMe, OCF 3 , OCHF 2 , OC 2 F 5 , SMe or SCF 3 ,
or
R 2 represents naphthalen-1-yl, naphthalen-2-yl, 1,2,3,4-tetrahydronaphthalen-1-yl, 1,2,3,4-tetrahydronaphthalen-2-yl, 5,6,7,8-tetrahydronaphthalen-1-yl, 5,6,7,8-tetrahydronaphthalen-2-yl, decalin-1-yl, decalin-2-yl, 1H-inden-1-yl, 1H-inden-2-yl, 1H-inden-3-yl, 1H-inden-4-yl, 1H-inden-5-yl, 1H-inden-6-yl, 1H-inden-7-yl, indan-1-yl, indan-2-yl, indan-3-yl, indan-4-yl or indan-5-yl,
which may contain up to two substituents, where the substituents independently of one another are selected from the list below:
cyano, nitro, halogen, methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl, CF 3 , CHF 2 , C 2 F 5 , CCl 3 , —CH═CH 2 , —CH 2 CH═CH 2 , tri(methyl)silyl, benzyl, phenyl, OMe, OEt, OisoPr, OCF 3 , OCHF 2 , OC 2 F 5 , SMe or SCF 3 ,
or
R 2 represents furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, tetrazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,3-triazol-4-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 1,3,5-triazin-2-yl or 1,2,4-triazin-3-yl,
which may contain up to two substituents, where the substituents independently of one another are selected from the list below:
substituents at carbon:
cyano, nitro, halogen, methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl, CF 3 , CHF 2 , C 2 F 5 , CCl 3 , —CH═CH 2 , —CH 2 CH═CH 2 , tri(methyl)silyl, benzyl, phenyl, OMe, OEt, OisoPr, OCF 3 , OCHF 2 , OC 2 F 5 , SMe or SCF 3 ,
substituents at nitrogen:
methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl or phenyl,
or
R 2 represents indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzoxazol-7-yl, quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl or isoquinolin-8-yl,
which may contain up to two substituents, where the substituents independently of one another are selected from the list below:
substituents at carbon:
cyano, nitro, halogen, methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl, CF 3 , CHF 2 , C 2 F 5 , CCl 3 , —CH═CH 2 , —CH 2 CH═CH 2 , tri(methyl)silyl, benzyl, phenyl, OMe, OEt, OisoPr, OCF 3 , OCHF 2 , OC 2 F 5 , SMe or SCF 3 ,
substituents at nitrogen:
methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl or phenyl,
or
R 2 represents piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, piperazin-1-yl, piperazin-2-yl, piperazin-3-yl, morpholin-1-yl, morpholin-2-yl, morpholin-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 1,2,3,4-tetrahydroquinolin-1-yl, 1,2,3,4-tetrahydroisoquinolin-2-yl, 1,2,3,4-tetrahydroquinoxalin-1-yl, indolin-1-yl, isoindolin-2-yl, decahydroquinolin-1-yl or decahydroisoquinolin-2-yl,
which may contain up to two substituents,
where the possible substituents independently of one another are selected from the list below:
substituents at carbon:
cyano, nitro, halogen, methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl, CF 3 , CHF 2 , C 2 F 5 , CCl 3 , —CH═CH 2 , —CH 2 CH═CH 2 , tri(methyl)silyl, benzyl, phenyl, OMe, OEt, OisoPr, OCF 3 , OCHF 2 , OC 2 F 5 , SMe or SCF 3 ,
substituents at nitrogen:
methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl or phenyl,
and also agrochemically active salts thereof.
3 . Compounds of the formula (I) according to claim 1 or 2 in which the symbols have the meanings below:
A represents 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl,
G represents CH 2 ,
Y represents sulphur or oxygen,
R 1 represents hydrogen,
n=0 to 2,
R 2 represents naphthalen-1-yl, adamantan-1-yl, cyclohexyl, 1-phenyl-tetrazol-5-yl or quinolin-8-yl,
and also agrochemically active salts thereof.
4 . Method for controlling phytopathogenic harmful fungi, comprising applying compounds of the formula (I) according to claim 1 to the phytopathogenic harmful fungi and/or their habitat.
5 . Compositions for controlling phytopathogenic harmful fungi, characterized in that they comprise at least one compound of the formula (I) according to claim 1 , in addition to extenders and/or surfactants.
6 . A method of controlling phytopathogenic harmful fungi comprising contacting said fungi with thiazolylpiperidine derivatives of the formula (I) according to claim 1 .
7 . Process for preparing compositions for controlling phytopathogenic harmful fungi, comprising mixing thiazolylpiperidine derivatives of the formula (I) according to claim 1 with extenders and/or surfactants.
8 . Process for preparing the compounds of the formula (I), comprising at least one of steps (a) to (g) below:
in which R 1 , R 2 , A and G have the meanings given in claim 1 .
9 . Compounds of the formula (VI-a)
in which
PG represents acetyl, C 1 -C 4 -alkoxycarbonyl, benzyl or benzyloxycarbonyl,
W a represents bromine or iodine,
R 1 has the meanings given in claim 1 ,
and also salts thereof.
10 . Compounds of the formula (IV)
in which
PG represents acetyl, C 1 -C 4 -alkoxycarbonyl, benzyl or benzyloxycarbonyl,
R 1 and R 2 have the meanings given in claim 1 ,
and also salts thereof,
except for the compound tert-butyl 4-[4-({[4-(methylsulphonyl)phenyl]sulphanyl}methyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate.
11 . Compounds of the formula (III)
in which
R 1 and R 2 have the meanings given in claim 1 ,
and also salts thereof.
12 . (canceled)
13 . (canceled)
14 . (canceled)
15 . Compounds of the formula (IX),
in which
PG represents acetyl, C 1 -C 4 -alkoxycarbonyl, benzyl or benzyloxycarbonyl,
R 1 has the general, preferred, particularly preferred or very particularly preferred meanings given above,
W b represents iodine, bromine or iodine,
and also salts thereof.