Heteroarylpiperidine and -piperazine derivatives as fungicides

Patent metadata

Field	Value
Publication number	US-10499641-B2
Application number	US-201715714109-A
Country	US
Kind code	B2
Filing date	Sep 25, 2017
Priority date	Aug 25, 2010
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

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 formula (I)

A is pyrazol-1-yl which may contain up to two substituents, where the substituents are each independently selected from the following list:
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 -halocycloalkyl, 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,

R 3 and R 4 are the same or different and are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl,
L 1 is NH or CH 2 ,
Y is oxygen,
X is carbon,
R 2 is hydrogen,
R 10 is oxo, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl,
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 or halogen,
Q is

where the bond identified by “*” is bonded directly to G or L 2 , and where the bond identified by “#” is bonded directly to L 2 or G, or where the bond identified by “*” is bonded directly to L 2 , and the bond identified by “#” is at the same time bonded directly to G,

R 5 is hydrogen,
L 2 is a direct bond,
R 1 is phenyl which contains 1, 2 or 3 substituents, where the substituents are each independently selected at least once from Z 4 and optionally from the following list: fluorine, chlorine, bromine, iodine, cyano, nitro, hydroxyl, amino, —SH, —C(═O)H, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl, 1,2-dimethylethyl, ethenyl, ethynyl, trifluoromethyl, difluoromethyl, trichloromethyl, dichloromethyl, cyclopropyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, 1,1-dimethylethoxy, methylcarbonyl, ethylcarbonyl, trifluoromethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, 1,1-dimethylethoxycarbonyl, 1-ethenyloxy, 2-propenyloxy, 2-propynyloxy, methylcarbonyloxy, trifluoromethylcarbonyloxy, chloromethylcarbonyloxy, methylthio, ethylthio, methylsulphonyl, methylsulphonylamino, trifluoromethylsulphonylamino or -L 3 R 3 ,
L 3 is a direct bond, —CH 2 —, —C(═O)—, sulphur, oxygen, —C(═O)O—, —C(═O)NH—, —OC(═O)—or —NHC(═O)—,
Z 3 is a phenyl radical, naphthalenyl or a 5- or 6-membered heteroaryl radical which may contain up to two substituents, where the substituents are each independently selected from the following list:
substituents on carbon: halogen, cyano, nitro, hydroxyl, amino, —SH, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 2 -C 4 -alkoxyalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl or C 1 -C 4 -alkylamino, or di(C 1 -C 4 -alkyl)amino,
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 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl, benzyl, C 1 -C 4 -haloalkylsulphonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, phenylsulphonyl, C 1 -C 4 -alkylsulphonyl, —C(=O)H, or C 1 -C 3 -alkylcarbonyl,Z 4 is cyano-C 1 -C 6 -alkyl, C 2 -C 6 -alkenylcarbonyloxy, C 2 -C 6 -alkynylthio, C 3 -C 8 -halocycloalkylcarbonyloxy, C 2 -C 6 -alkenylamino, C 2 -C 6 -alkynylamino, C 1 -C 6 -haloalkylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxyamino, C 1 -C 6 -haloalkoxyamino, C 1 -C 6 -alkylcarbonylamino, C 1 -C 6 -haloalkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylcarbonyl(C 1 -C 6 -alkyl)amino, C 1 -C 6 -haloalkylcarbonyl(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkoxycarbonyl(C 1 -C 6 -alkyl)amino, —NR 3 SO 2 Z 3 , C 2 -C 6 -alkenylthio, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkylcarbonyl, -SF 5, C 1 -C 6 -haloalkoxycarbonylamino, —NHC(═O)H, C 1 -C 6 -alkoxy(C 1 -C 4 -alkyl)aminocarbonyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkoxy, —C(═NOR 7 )R 8 , —N=C(R 9 ) 2 , di(C 1 -C 6 -alkyl)aminocarbonylamino, di(C 1 -C 6 -alkyl)aminosulphonyl, di(C 1 -C 6 -haloalkyl)amino, C 1 -C 6 -alkylaminosulphonyl, C 1 -C 6 -alkylaminocarbonylamino, tri(C 1 -C 4 -alkyl)silyloxy, C 1 -C 6 -haloalkylsulphonyloxy, C 1 -C 6 -alkylsulphonyloxy, tri(C 1 -C 4 -alkyl)silyl-C 2 -C 4 -alkynyloxy, tri(C 1 -C 4 -alkyl)silyl-C 2 -C 4 -alkynyl or -L 4 Z 3 ,

Z 4 is cyano-C 1 -C 6 -alkyl, C 2 -C 6 -alkenylcarbonyloxy, C 2 -C 6 -alkynylthio, C 3 -C 8 -halocyclo-alkylcarbonyloxy, C 2 -C 6 -alkenylamino, C 2 -C 6 -alkynylamino, C 1 -C 6 -haloalkylamino, C 3 -C 8 -cycloalkyl-C 1 -C 6 -alkylamino, C 1 -C 6 -alkoxyamino, C 1 -C 6 -haloalkoxyamino, C 1 -C 6 -alkyl-carbonylamino, C 1 -C 6 -haloalkylcarbonylamino, C 1 -C 6 -alkoxycarbonylamino, C 1 -C 6 -alkylcarbonyl(C 1 -C 6 -alkyl)amino, C 1 -C 6 -haloalkylcarbonyl(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkoxycarbonyl(C 1 -C 6 -alkyl)amino, -NR 3 SO 2 Z 3 , C 2 -C 6 -alkenylthio, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkylcarbonyl, -SF 5 , C 1 -C 6 -haloalkoxycarbonylamino, —NHC(═O)H, C 1 -C 6 -alkoxy(C 1 -C 4 -alkyl)aminocarbonyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkoxy, —C(═NOR 7 )R 8 , —N═C(R 9 ) 2 , di(C 1 -C 6 -alkyl)aminocarbonylamino, di(C 1 -C 6 -alkyl)aminosulphonyl, di(C 1 -C 6 -haloalkyl)amino, C 1 -C 6 -alkylaminosulphonyl, C 1 -C 6 -alkylaminocarbonylamino, tri(C 1 -C 4 -alkyl)silyloxy, C 1 -C 6 -haloalkylsulphonyloxy, C 1 -C 6 -alkylsulphonyloxy, tri(C 1 -C 4 -alkyl)silyl-C 2 -C 4 -alkynyloxy, tri(C 1 -C 4 -alkyl)silyl-C 2 -C 4 -alkynyl or -L 4 Z 3 ,
or
Z 4 is —C(═O)NR 11 R 12 , —SO 2 NR 11 R 12 , -SCN, C 1 -C 3 -alkoxysulphonyl, C 3 -C 8 -cycloalkylsulphinyl or cyano(C 1 -C 3 -alkoxy)-C 1 -C 3 -alkyl,
or
Z 4 is C 1 -C 3 -alkyl which contains 1 or 2 substituents, where the substituents are each independently selected from the following list:
C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkynyloxy, C 2 -C 4 -alkenylthio, C 2 -C 4 -alkynylthio, C 1 -C 3 -alkoxy-C 1 -C 3 -alkylthio, C 1 -C 3 -alkoxy-C 1 -C 3 -alkylsulphinyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkylsulphonyl, C 1 -C 3 -alkylcarbonyloxy or C 1 -C 3 -halocarbonyloxy,

or
Z 4 is substituted hydroxyl, where the substituents are each selected from the following list:
C 3 -C 8 -cycloalkylsulphonyl, C 3 -C 8 -halocycloalkylsulphonyl, C 2 -C 4 -alkenylsulphonyl or C(═O)NR 3 R 4 , or

Z 4 is C 1 -C 3 -alkoxy which contains 1 or 2 substituents, where the substituents are each independently selected from the following list:
cyano, C 1 -C 3 -alkylcarbonyloxy, C 1 -C 3 -alkoxycarbonyl, C 3 -C 8 -cycloalkoxy, C 1 -C 3 -alkylcarbonyloxy, —O(C═O)H, C 1 -C 3 -alkylthio, hydroxy-C 1 -C 3 -alkyl, C 3 -C 8 -cycloalkylsulphonyl, C 1 -C 3 -haloalkylsulphonyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkoxy, C 1 -C 3 -alkylsulphonyl,

R 7 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, benzyl or Z 3 ,
R 8 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 4 -alky

Assignees

• Bayer Cropscience Ag

Inventors

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

Classifications

• A01N47/22

  O-Aryl or S-Aryl esters thereof · CPC title

• C07D417/14 Primary

  containing three or more hetero rings · CPC title

• A01N43/80 Primary

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

• A01N47/38

  containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof · CPC title

• A01N55/00

  Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00) · CPC title