Malonic ester derivatives of heteroarylpiperidines and -piperazines as fungicides

Patent metadata

Field	Value
Publication number	US-9924721-B2
Application number	US-201414914230-A
Country	US
Kind code	B2
Filing date	Aug 26, 2014
Priority date	Aug 28, 2013
Publication date	Mar 27, 2018
Grant date	Mar 27, 2018

Abstract

Malonic ester derivatives of the formula (I)

in which the symbols A 1 , A 2 , Y, R 10 , p, X, R 2 , G, Q, L 2 and R 1 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)

or a salt, metal complex, or N-oxide thereof, in which:
A 1 is —C(═O)R L1 ,
A 2 is hydrogen, chloro, bromine, iodine, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -haloalkylsulphonyl, phenylsulphonyl, C 1 -C 4 -alkylsulphonyloxy, C 1 -C 4 -haloalkylsulphonyloxy, or phenyl-sulphonyloxy, wherein phenyl is optionally substituted by one, two or three groups independently selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, and C 1 -C 4 -haloalkoxy, or
A 2 is a heteroaromatic radical selected from the group consisting of 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, pyrimidin-2-yl, pyrimidin-4-yl and pyrimidin-5-yl, which optionally contains one or two substituents, where the optional substituents on ring carbon atoms are the same or different and are each independently selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, 1-methylethyl, 1,1-dimethylethyl, chlorofluoromethyl, dichloromethyl, dichlorofluoromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, cyclopropyl, ethoxy, 1-methylethoxy, n-propoxy, methoxy, trifluoromethoxy, difluoromethoxy, 1-methylethylthio, methylthio, ethylthio, n-propylthio, difluoromethylthio, trifluoro-methylthio and phenyl and where the optional substituents on ring nitrogen atoms are the same or different and are each independently selected from the group consisting of methyl, ethyl, n-propyl, 1-methylethyl, methylsulphonyl, trifluoromethylsulphonyl, methylcarbonyl, trifluoromethylcarbonyl, chloromethylcarbonyl, 2,2-trifluoroethyl, 2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2-chloro-2-difluoroethyl or 2-chloro-2-fluoroethyl, and trifluoromethyl,
Y is oxygen,
R L1 is amino, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1,1-dimethylethoxy, 1,2-dimethylethoxy, n-pentyloxy, n-hexyloxy, n-octyloxy, 1-ethylhexyloxy, 2-ethyl-hexyloxy, 2,2,2-trifluoroethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, allyloxy, but-2-en-1-yloxy, prop-2-yn-1-yloxy, phenoxy, 2,6-dimethylphenoxy, 2,6-diisopropylphenoxy, 2,6-di-tert-butylphenoxy, benzyloxy, 4-methoxybenzyloxy, or 3,4-dimethoxybenzyloxy,
X is carbon,
R 2 is hydrogen, fluorine, methoxy or hydroxyl,
R 10 is hydrogen, fluorine, methoxy or hydroxyl,
p is 0,
G is

where the bond identified by v is bonded directly to X and the bond identified by w is bonded directly to Q,

R G1 is hydrogen,
Q is

where the bond identified by x is bonded directly to G and the bond identified by y is bonded directly to L 2 ,

R 5 is hydrogen, cyano, methyl, trifluoromethyl, difluoromethyl or methoxymethyl,
L 2 is a direct bond, —C(═O)—, —CHR 20 — or —NR 21 —,
R 20 is hydrogen, methyl, ethyl, trifluoromethyl,
R 21 is hydrogen or methyl,
R 1 is substituted cyclopentenyl, cyclohexenyl, cyclopentyl, cyclohexyl or cycloheptyl, each of which contains 1 or 2 substituents, where the substituents are each independently at least one substituent Z 4 and optionally also one substituent selected from the group consisting of methyl, ethyl, methoxy, ethoxy, trifluoro-methoxy, ethynyl, 2-propenyloxy, 2-propynyloxy, methylcarbonyloxy, ethylcarbonyloxy, trifluorocarbonyloxy, methylthio, ethylthio and trifluoromethylthio, or
R 1 is phenyl which contains 1, 2 or 3 substituents, where the substituents are each independently at least one substituent Z 4 and optionally also 1 or 2 substituents selected from the group consisting of 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, chloromethyl-carbonyloxy, methylthio, ethylthio, methylsulphonyl, or -L 3 Z 3 , or
R 1 is 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-tetrahydro-naphthalen-2-yl, decalin-1-yl, decalin-2-yl, 1H-inden-1-yl, 2,3-dihydro-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, where each is substituted by at least one substituent Z 4 and optionally further substituents independently selected from Z 4 and the group consisting of methyl, methoxy, cyano, fluorine, chlorine, bromine and iodine, or
R 1 is 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, 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 or pyrazin-2-yl, each of which contains 1 or 2 substituents, where the substituents are each independently at least one substituent Z 4 and a further optional substituent that is Z 4 , oxo, or thio, or is a substituent on a ring carbon atom selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro, hydroxyl, amino, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl, 1,2-dimethyl-ethyl, ethenyl, ethynyl, trifluoromethyl, difluoromethyl, trichloromethyl, dichloromethyl, cyclopropyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, 1,1-dimethylethoxy, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, 1,1-dimethylethoxycarbonyl, methylcarbonyloxy, methylthio, ethylthio and methylsulphonyl, or is a substituent on a ring nitrogen atom selected from the group consisting of methyl, ethyl, n-propyl, —C(═O)H, methylcarbonyl, trifluoromethylcarbonyl, chloromethylcarbonyl, methylsulphonyl, trifluoromethyl-sulphonyl, phenylsulphonyl, phenyl and 2-propynyl, or
R 1 is 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-benzo-furan-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benz

Assignees

• Bayer Cropscience Ag

Inventors

• Hillebrand Stefan
• Riedrich Matthias
• Hoffmann Sebastian
• Ford Mark James
• Telser Joachim
• Es-Sayed Mazen
• Hoemberger Guenter
• Wasnaire Pierre
• Wachendorff-Neumann Ulrike
• Tsuchiya Tomoki
• Toquin Valerie

Classifications

• A01N43/78 Primary

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

• A01N43/82

  five-membered rings with three ring hetero atoms · 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

• C07D417/14

  containing three or more hetero rings · CPC title