1,2,4-Triazole derivatives and fungicidal composition containing the same

Claim 2

A 1,2,4-triazole derivative of the general formula ##STR297## wherein X may be the same or different and denotes a halogen atom, a (C 1 -C 4 )alkyl group, a (C 1 -C 4 )alkoxyl group, a (C 1 -C 4 )alkylthio group, a (C 1 -C 4 )alkylsulfinyl group, a (C 1 -C 4 )alkylsulfonyl group, a trifluoromethyl group, a nitro group or a cyano group; n is an integer of 0 to 5; R denotes a (C 1 -C 4 )alkyl group, a (C 2 -C 4 )alkenyl group, a (C 2 -C 4 )alkynyl group, a (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl group, a (C 1 -C 4 )alkylthio-(C 1 -C 4 )alkyl group, a (C 3 -C 6 )cycloalkyl group, a (C 3 -C 6 )cycloalkyl-(C 1 -C 4 )alkyl group, a phenyl group, a mono-halophenyl group, a di-halophenyl group, a tri-halophenyl group, or a phenyl(C 1 -C 4 )alkyl group of which the phenyl may optionally bear up to three substituents selected from a halogen atom, a (C 1 -C 4 )alkyl group, a (C 1 -C 4 )alkoxyl group, a (C 1 -C 4 )alkylthio group, a (C 1 -C 4 )alkylsulfonyl group, trifluoromethyl group, cyano group and nitro group, these substituents being the same or different from each other; Y denotes an oxygen atom or a sulfur atom; and Z denotes a linear or branched (C 1 -C 6 )alkylene group, and a salt of said 1,2,4-triazole derivative.

Claim 3

A 1,2,4-triazole derivative of claim 1 which is of the general formula ##STR298## wherein A denotes a phenyl group, a chlorophenyl group, a bromophenyl group, a fluorophenyl group, an iodophenyl group, a cyanophenyl group, a nitrophenyl group, a trifluoromethylphenyl group, a dichlorophenyl group, a dibromophenyl group, a difluorophenyl group, a bromochlorophenyl group, a chlorofluorophenyl group, a chloroiodophenyl group, a trifluoromethylchlorophenyl group, a trichlorophenyl group, a dichlorofluorophenyl group, a methylchlorophenyl group, a methylnitrophenyl group, a methylcyanophenyl group, a trifluoromethyl-methylphenyl group, a trifluoromethyl-dichlorophenyl group, a methoxychlorophenyl group, a methoxydichlorophenyl group, a (C 1 -C 4 )alkylphenyl group, a di-(C 1 -C 4 )alkylphenyl group, a (C 1 -C 4 )alkoxyphenyl group, a (C 1 -C 4 )alkylthiophenyl group, a (C 1 -C 4 )alkylsulfinylphenyl group, a (C 1 -C 4 )alkylsulfonylphenyl group or a (C 1 -C 4 )alkylsulfonyl-bromophenyl group; R 1 denotes a (C 1 -C 4 )alkyl group, a (C 2 -C 4 )alkenyl group, a (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl group, a methylthio(C 1 -C 4 )alkyl group, a cyclohexyl group, a cyclopentyl group, a cyclopentyl-(C 1 -C 4 )alkyl group, a benzyl group, a chlorobenzyl group, a fluorobenzyl group, an iodobenzyl group, a cyanobenzyl group, a nitrobenzyl group, a dichlorobenzyl group, a trichlorobenzyl group, a chlorobromobenzyl group, a chlorofluorobenzyl group, a chlorocyanobenzyl group, a chloro-trifluoromethylbenzyl group, a mono- or di-(C 1 -C 4 )alkylbenzyl group, a (C 1 -C 4 )alkoxybenzyl group, a (C 1 -C 4 )alkyl-chlorobenzyl group, a (C 1 -C 4 )alkyl-nitrobenzyl group, a (C 1 -C 4 )alkylthiobenzyl group, a methylsulfonylbenzyl group, a methylsulfonyl-chlorobenzyl group, an ethylsulfinylbenzyl group, a phenylethyl group, a methyldichlorophenylethyl group, a 1-phenyl-propyl group, a 1-chlorophenyl-propyl group, a phenyl group, a chlorophenyl group, a dichlorophenyl group, a dichlorofluorophenyl group, or a (C 2 -C 4 )alkynyl group; Y is an oxygen atom or a sulfur atom; Z' is a linear (C 1 -C 3 )alkylene group; and B is a hydrogen atom or a (C 1 -C 4 )alkyl group, and a salt of said 1,2,4-triazole derivative.

Claim 4

The compound of claim 2 in which A is a chlorophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a dichlorophenyl group, a chlorofluorophenyl group or a trifluoromethyl-chlorophenyl group.

Claim 5

The compound of claim 2 in which R 1 is a benzyl group, a monochlorobenzyl group or a dichlorobenzyl group.

Claim 6

The compound of claim 2 in which Z' is a methylene group (--CH 2 --) when B is the hydrogen atom.

Claim 7

The compound of claim 2 in which Z' is a methine group when B is a methyl group.

Claim 8

The compound of claim 2 in which Y is the sulfur atom; A is a chlorophenyl group, a fluorophenyl group, a trifluoromethylphenyl group, a dichlorophenyl group, a chlorofluorophenyl group or a trifluoromethyl-chlorophenyl group; R 1 is a benzyl group, a monochlorobenzyl group or a dichlorobenzyl group; Z' is a methylene group when B is the hydrogen atom, or Z' is a methine group when B is the methyl group.

Claim 9

A 1,2,4-triazole derivative of claim 2 which is of the general formula ##STR299## wherein A' denotes a 2,4-dichlorophenyl group, a 2-chloro-4-fluorophenyl group, or a 2-trifluoromethyl-4-chlorophenyl group; R 2 denotes a benzyl group, a 4-chlorobenzyl group, a 2,4-dichlorobenzyl group or a 3,4-dichlorobenzyl group, and B' denotes a hydrogen atom or a methyl group, and a salt of said 1,2,4-triazole derivative.

Claim 10

A 1,2,4-triazole derivative of claim 2 which is of the general formula ##STR300## wherein A" denotes a phenyl group, a chlorophenyl group, a bromophenyl group, a fluorophenyl group, an iodophenyl group, a cyanophenyl group, a nitrophenyl group, a trifluoromethylphenyl group, a dichlorophenyl group, a difluorophenyl group, a bromochlorophenyl group, a chlorofluorophenyl group, a chloroiodophenyl group, a trifluoromethylchlorophenyl group, a trichlorophenyl group, a dichlorofluorophenyl group, a methylchlorophenyl group, a methylnitrophenyl group, a methylcyanophenyl group, a trifluoromethyl-dichlorophenyl group, a methoxychlorophenyl group, a methoxy-dichlorophenyl group, a (C 1 -C 4 )alkylphenyl group a di-(C 1 -C 4 )alkylphenyl group, a (C 1 -C 4 )alkoxyphenyl group, a (C 1 -C 4 )alkylthiophenyl group, a (C 1 -C 4 )alkylsulfonylphenyl group or a (C 1 -C 4 )alkylsulfonyl-bromophenyl group; R 3 denotes a (C 1 -C 4 )alkyl group, a (C 2 -C 4 )alkenyl group, a (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl group, a methylthio(C 1 -C 4 )alkyl group, a cyclohexyl group, a cyclopentyl group, a cyclopentyl-(C 1 -C 4 )alkyl group, a benzyl group, a chlorobenzyl group, a fluorobenzyl group, a cyanobenzyl group, a dichlorobenzyl group, a chlorobromobenzyl group, a chlorofluorobenzyl group, a chlorocyanobenzyl group, a mono- or di-(C 1 -C 4 )alkylbenzyl group, a (C 1 -C 4 )alkoxybenzyl group, a (C 1 -C 4 )alkyl-chlorobenzyl group, a (C 1 -C 4 )alkylthiobenzyl group, a methylsulfonylbenzyl group, a phenylethyl group, a methyldichlorophenylethyl group, a 1-chlorophenyl-propyl group, a phenyl group, a chlorophenyl group, a dichlorophenyl group, a dichlorofluorophenyl group, or a (C 2 -C 4 )alkynyl group; Z' is a linear (C 1 -C 3 )alkylene group; and B is a hydrogen atom or a (C 1 -C 4 )alkyl group, and a salt of said 1,2,4-triazole derivative.

Claim 11

A 1,2,4-triazole derivative as claimed in claim 1 which is: ##STR301## where each Tz denotes the 1,2,4-triazole-1-yl group of the formula ##STR302##

Claim 12

A fungicidal composition comprising as the active ingredient a fungicidally effective amount of a 1,2,4-triazole derivative as defined in claim 1, or a salt thereof, in association with an acceptable carrier for the active ingredient.

Claim 13

A method of combating the fungal pests of plants, which comprises treating plants, seeds or trees with a fungicidally effective amount of a 1,2,4-triazole derivative as defined in claim 1 or a salt thereof.