Heteroaryl piperidine and heteroaryl piperazine derivatives as fungicides
View Patent ↗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 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 or trifluoromethyl,
L 1 is —CH 2 —,
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,
where the bond identified by “x” is bonded directly to G, and the bond identified by “y” is bonded directly to L 2 ,
L 2 is a direct bond,
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 allyloxy,
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
A is 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl, or 3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl.
3. The compound of the formula (I) and/or a salt, metal complex and/or an N-oxide thereof according to claim 1 , wherein
Z 1-1 is present in the compound and is selected from halogen and C 1 -C 6 -alkyl.
4. 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, or 2-(allyloxy)-3-fluorophenyl.
5. A compound of the formula (VII)
and/or a salt, metal complex and/or an N-oxide thereof, in which the radicals are each 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,
where the bond identified by “x” is bonded directly to G, and the bond identified by “y” is bonded directly to L 2 ,
L 2 is a direct bond,
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 allyloxy,
Z 1-1 is halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl,
and W 13 is a leaving group.
6. 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 remaining radicals are each 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,
where the bond identified by “x” is bonded directly to G, and the bond identified by “y” is bonded directly to L 2 ,
L 2 is a direct bond,
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 allyloxy,
Z 1-1 is halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl.
7. A compound of the formula (XIIIa)
and/or a salt, metal complex and/or an N-oxide thereof, in which the radicals are each 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,
where the bond identified by “x” is bonded directly to G, and the bond identified by “y” is bonded directly to L 2 ,
L 2 is a direct bond,
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 allyloxy,
Z 1-1 is halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl.
8. A composition for controlling phytopathogenic harmful fungi, comprising at least one compound according to claim 1 and one or more extenders and/or surfactants.
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. The method according to claim 9 comprising treatment of transgenic plants.
11. A process for producing a compositions for controlling phytopathogenic harmful fungi, comprising mixing a compound according to claim 1 , with one or more extenders and/or surfactants.