Heteroaryl piperidine and heteroaryl piperazine derivatives as fungicides
Heteroarylpiperidine and -piperazine derivatives of the formula (I) in which the symbols A, X, Y, L 1 , L 2 , G, Q, p, R 1 , R 2 and R 10 are each as defined in the description, and salts, metal complexes and N-oxides of the compounds of the formula (I), and the use thereof for controlling phytopathogenic harmful fungi and processes for preparing compounds of the formula (I).
1. A compound of the formula (I)
in which the radicals are each defined as follows:
A is phenyl which may contain up to two substituents, where the substituents are each independently selected from the following list:
halogen, cyano, hydroxyl, —NR 3 R 4 , —C(═O)NR 3 R 4 , nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkenyloxy, C 1 -C 4 -alkynyloxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkoxy-C 1 -C 6 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyloxy or —C(═O)H, or
A is a heteroaromatic radical selected from the following group: 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, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl which may contain up to two substituents, where the substituents are each independently selected from the following list:
substituents on carbon:
halogen, cyano, hydroxyl, nitro, —NR 3 R 4 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalykl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyloxy or phenyl,
substituents on nitrogen:
C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 10 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkylcarbonyl, phenyl, benzyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, phenylsulphonyl, —C(═O)H, or C 1 -C 6 -alkylcarbonyl,
L 1 is —NH—,
Y is oxygen,
X is carbon,
R 2 is hydrogen,
p is 0,
G is
where the bond identified by “v” is bonded directly to X and where the bond identified by “w” is bonded directly to Q,
R G1 is hydrogen,
Q is
R 5 is hydrogen,
L 2 is a direct bond,
where the bond identified by “x” is bonded directly to G, and the bond identified by “y” is bonded directly to L 2 ,
R 1 is phenyl which is substituted once by a Z 4 substituent and may additionally optionally have further substitution, where the additional substituents are each independently selected from Z 4 and Z 1-1 ,
Z 4 is C 1 -C 3 -alkoxy-C 2 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -alkylsulphinyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulphonyl-C 1 -C 2 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 2 -alkyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylsulphonylamino,
Z 1-1 is halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl;
and/or a salt, metal complex and/or an N-oxide thereof.
2. The compound of the formula (I) and/or a salt, metal complex and/or an N-oxide thereof according to claim 1 , wherein the radical definitions are as follows:
A is phenyl which may contain up to two substituents, where the substituents are each independently selected from the following list:
methyl, ethyl, iodine, chlorine, bromine, fluorine, methoxy, ethoxy, difluoromethyl or trifluoromethyl or
A is pyrazol-1-yl which may contain up to two substituents, where the substituents are each independently selected from the following list:
methyl, ethyl, chlorine, bromine, fluorine, difluoromethyl or trifluoromethyl.
3. The compound of the formula (I) and/or a salt, metal complex and/or an N-oxide thereof according to claim 1 , wherein
A is 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl, 3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl, 3-(difluoromethyl)-5-methyl-1H-pyrazol-1-yl, 5-(difluoromethyl)-3-methyl-1H-pyrazol-1-yl, 2,5-bis(difluoromethyl)phenyl, 2,5-dimethylphenyl or 5-chloro-2-methylphenyl.
4. The compound of the formula (I) and/or a salt, metal complex and/or an N-oxide thereof according to claim 1 , wherein
Z 4 is C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy or C 1 -C 4 -alkylsulphonylamino, and
Z 1-1 is selected from halogen and C 1 -C 6 -alkyl.
5. The compound of the formula (I) and/or a salt, metal complex and/or an N-oxide thereof according to claim 1 , wherein
R 1 is 2-(allyloxy)phenyl, 3-(allyloxy)phenyl, 3-(allyloxy)-2,6-difluorophenyl, 2-(allyloxy)-4-methylphenyl, 2-(allyloxy)-4,6-dichlorophenyl, 2-(allyloxy)-6-fluorophenyl, 2-(allyloxy)-6-chlorophenyl, 2-(allyloxy)-3-fluorophenyl, 3-formylphenyl, 2-formylphenyl, 2-fluoro-6-formylphenyl, 2-(prop-2-yn-1-yloxy)phenyl, 2, 6-difluoro-3-(prop-2-yn-1-yloxy)phenyl, 3-fluoro-2-(prop-2-yn-1-yloxy)phenyl, 3-(prop-2-yn-1-yloxy)phenyl, 2-chloro-6-(prop-2-yn-1-yloxy)phenyl, 4-chloro-2-(prop-2-yn-1-yloxy)phenyl, 2,4-dichloro-6-(prop-2-yn-1-yloxy)phenyl, 2-fluoro-6-(prop-2-yn-1-yloxy)phenyl, 4-methyl-2-(prop-2-yn-1-yloxy)phenyl, 2-(but-2-yn-1-yloxy)-4-methoxyphenyl or 2-[(methyl-sulphonyl)amino]phenyl.
6. A compound of the formula (VII)
and/or a salt, metal complex and/or an N-oxide thereof, in which the radicals are each as defined as follows:
X is carbon,
R 2 is hydrogen,
p is 0,
G is
where the bond identified by “v” is bonded directly to X and where the bond identified by “w” is bonded directly to Q,
R G1 is hydrogen,
Q is
R 5 is hydrogen,
L 2 is a direct bond,
where the bond identified by “x” is bonded directly to G, and the bond identified by “y” is bonded directly to L 2 ,
R 1 is phenyl which is substituted once by a Z 4 substituent and may additionally optionally have further substitution, where the additional substituents are each independently selected from Z 4 and Z 1-1 ,
Z 4 is C 1 -C 3 -alkoxy-C 2 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -alkylsulphinyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulphonyl-C 1 -C 2 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 2 -alkyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylsulphonylamino,
Z 1-1 is halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl;
and W 13 is a leaving group.
7. A compound of the formula (XVIId)
and/or a salt, metal complex and/or an N-oxide thereof, in which the symbol W 6 is acetyl, C 1 -C 4 alkoxycarbonyl, benzyl or benzyloxycarbonyl and the radicals are each as defined as follows:
X is carbon,
R 2 is hydrogen,
p is 0,
G is
where the bond identified by “v” is bonded directly to X and where the bond identified by “w” is bonded directly to isoxazole ring,
R G1 is hydrogen,
R 5 is hydrogen,
L 2 is a direct bond,
where the bond identified by “x” is bonded directly to G, and the bond identified by “y” is bonded directly to L 2 ,
R 1 is phenyl which is substituted once by a Z 4 substituent and may additionally optionally have further substitution, where the additional substituents are each independently selected from Z 4 and Z 1-1 ,
Z 4 is C 1 -C 3 -alkoxy-C 2 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -alkylsulphinyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulphonyl-C 1 -C 2 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 2 -alkyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylsulphonylamino,
Z 1-1 is halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl.
8. A compound of the formula (XIIIa)
and/or a salt, metal complex and/or an N-oxide thereof, in which the radicals are each as defined as follows:
X is carbon,
R 2 is hydrogen,
p is 0,
G is
where the bond identified by “v” is bonded directly to X and where the bond identified by “w” is bonded directly to isoxazole ring,
R G1 is hydrogen,
R 5 is hydrogen,
L 2 is a direct bond,
where the bond identified by “x” is bonded directly to G, and the bond identified by “y” is bonded directly to L 2 ,
R 1 is phenyl which is substituted once by a Z 4 substituent and may additionally optionally have further substitution, where the additional substituents are each independently selected from Z 4 and Z 1-1 ,
Z 4 is C 1 -C 3 -alkoxy-C 2 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -alkylsulphinyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkylsulphonyl-C 1 -C 2 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 2 -alkyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylsulphonylamino,
Z 1-1 is halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl.
9. A method for controlling phytopathogenic harmful fungi, comprising applying a compound according to claim 1 to the phytopathogenic harmful fungi and/or a habitat thereof.
10. A composition for controlling phytopathogenic harmful fungi, comprising at least one compound according to claim 1 and one or more extenders and/or surfactants.
11. A process for producing compositions for controlling phytopathogenic harmful fungi, comprising mixing a compound according to claim 1 , with one or more extenders and/or surfactants.
12. The method according to claim 9 , comprising treatment of transgenic plants.
13. A method for controlling phytopathogenic harmful fungi, comprising applying a compound according to claim 1 to a seed.