Heteroaryl piperidine and heteroaryl piperazine derivatives as fungicides

Patent metadata

Field	Value
Publication number	US-9975889-B2
Application number	US-201615339576-A
Country	US
Kind code	B2
Filing date	Oct 31, 2016
Priority date	Oct 27, 2010
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

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).

First claim

The invention claimed is:

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

Assignees

• Bayer Ip Gmbh

Inventors

• Hillebrand Stefan
• Cristau Pierre
• Hoffmann Sebastian
• Kluth Joachim
• Wasnaire Pierre
• Tsuchiya Tomoki
• Benting Juergen
• Wachendorff-Neumann Ulrike
• Seitz Thomas

Classifications

• A01N43/78

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title

• C07D417/14 Primary

  containing three or more hetero rings · CPC title

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title