# US 4,391,804 A · Imidazole derivatives and fungicidal composition containing the same

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- Number: US 4,391,804 A
- Document ID: US4391804A
- Status: Granted
- Kind: A
- Application number: 06/358,533
- Filed: 1982-03-16
- Granted: 1983-07-05
- Earliest claimed: 1982-03-16
- Assignees: Hokko Chemical Industry Co., Ltd.
- Inventors: Hiroshi Ohyama; Ken Morita; Takuo Wada; Masahiko Miyahara
- Web page: https://patentgrep.com/patent/US4391804A

## CPC

- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A01N 43/50: 1,3-Diazoles; Hydrogenated 1,3-diazoles
- C07D 233/56: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

A new imidazole compound is now provided, which is represented by the general formula ##STR1## wherein R.sub.1 is naphthyl group, an arylalkyl group, a cycloalkyl group, a cycloalkylalkyl group, an alkyl group, a lower alkenyl group, a lower alkoxy-lower alkyl group or a phenylthio-lower alkyl group or phenyl group or a substituted phenyl group; R.sub.2 is an unsubstituted or substituted alkyl group or an alkenyl group or an alkynyl group, naphthyl group, or an unsubstituted or substituted phenyl group; X is an oxygen atom or a sulfur atom; and Y is an unsubstituted or substituted alkylene group or an unsubstituted or substituted alkenylene group. The new imidazole compound and its salt show a usefully high fungicidal activity against a wide variety of fungi which infest crop plants. The new imidazole compound and its salt may be useful as fungicidal agent of agricultural and horticultural usages.

## Claims

### Claim 1

An imidazole derivative of the general formula ##STR250## wherein R.sub.1 is naphthyl group, an arylalkyl group, a cycloalkyl group, a cycloalkylalkyl group, an alkyl group, a lower alkenyl group, a lower alkoxy-lower alkyl group, a phenylthio-lower alkyl group or phenyl group; the phenyl group being unsubstituted or substituted with 1 to 5 substituents which is or are the same or different from each other and selected from a halogen atom, nitro group, cyano group, a lower alkyl group, a lower alkenyl group, a halogenated lower alkyl group, a lower alkoxyl group, a lower alkenyloxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a lower alkylcarbonyl group, phenyl group, phenoxy group, a halogen-substituted phenoxy group, phenylthio group, a lower alkyl-substituted phenylthio group and a nitro-substituted phenylthio group; R.sub.2 is a saturated alkyl group, an unsaturated alkyl group, a lower alkoxy-lower alkyl group, a lower alkylthio-lower alkyl group, a phenoxy-lower alkyl group, a phenylthio-lower alkyl group, a mono- or di-lower alkylamino-lower alkyl group, a lower alkyl group substituted with a group --N(CH.sub.2).sub.n where n is an integer of 2 to 6, a lower alkylcarbonyl group, phenylcarbonyl group, a cycloalkyl group, a cycloalkylalkyl group, a halogenated lower alkyl group, a cyano-lower alkyl group, a lower alkoxycarbonyl-lower alkyl group, a lower alkylthiocarbonyl-lower alkyl group, an arylalkyl group, a lower alkylcarbonyl-lower alkyl group, a phenylcarbonyl-lower alkyl group, naphthyl group, furfuryl group or phenyl group; the latter phenyl group being unsubstituted or substituted with a substitutent which is selected from a halogen atom, nitro group, cyano group and a lower alkyl group;
X is an oxygen atom or a sulfur atom; and
Y is a straight or branched saturated alkylene group or unsaturated alkylene group, the saturated alkylene group being unsubstituted or substituted with a halogen group, a lower alkoxyl group, cyano group, phenyl group, a halogen-substituted phenyl group, a nitro-substituted phenyl group, a lower alkyl-substituted phenyl group and/or trifluoromethyl-substituted phenyl group, and a salt of said imidazole derivative.

### Claim 2 (depends on 1)

An imidazole derivative as claimed in claim 1 which is of the formula ##STR251## wherein R.sub.3 is naphthyl group, a phenyl-(C.sub.1 -C.sub.4)alkyl group, a dichlorophenyl-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.5 -C.sub.6)cycloalkyl group, a (C.sub.5 -C.sub.6)cycloalkyl-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.1 -C.sub.10) alkyl group, a (C.sub.2 -C.sub.4)alkenyl group, a (C.sub.1 -C.sub.4)alkoxy-(C.sub.1 -C.sub.4)alkyl group, a phenylthio-(C.sub.1 -C.sub.4)alkyl group, phenyl group, a chlorophenyl group, a fluorophenyl group, a bromophenyl group, a nitrophenyl group, a cyanophenyl group, a trifluoromethylphenyl group, a dichlorophenyl group, a dibromophenyl group, a difluorophenyl group, a bromochlorophenyl group, a chlorofluorophenyl group, a trifluromethylchlorophenyl group, a trichlorophenyl group, a dichlorodimethylphenyl group, a trichloro-dimethylphenyl group, a chloro-methoxyphenyl group, a chloro-methylphenyl group, a (C.sub.1 -C.sub.4)alkylphenyl group, a di-(C.sub.1 -C.sub.4)alkylphenyl group, a (C.sub.2 -C.sub.4)alkenylphenyl group, a (C.sub.2 -C.sub.4)alkenyloxyphenyl group, a (C.sub.1 -C.sub.4)alkoxyphenyl group, a di-(C.sub.1 -C.sub.4)alkoxyphenyl group, a (C.sub.1 -C.sub.4)alkylthiophenyl group, a (C.sub.1 -C.sub.4)alkylsulfinylphenyl group, a (C.sub.1 -C.sub.4)alkylsulfonylphenyl group, a (C.sub.1 -C.sub.4)alkylcarbonylphenyl group, diphenyl group, phenoxyphenyl group, a chlorophenoxyphenyl group, a phenylthiophenyl group, a (C.sub.1 -C.sub.4)alkylphenylthiophenyl group or a nitrophenylthiophenyl group,
R.sub.4 is a (C.sub.1 -C.sub.10)alkyl group, a (C.sub.2 -C.sub.4)alkenyl group, a (C.sub.2 -C.sub.4)alkynyl group, a (C.sub.1 -C.sub.4)alkoxy-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.5 -C.sub.6)cycloalkyl-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.1 -C.sub.4)alkylthio-(C.sub.1 -C.sub.4)alkyl group, a phenyl-(C.sub.1 -C.sub.4)alkyl group, a phenoxy-(C.sub.1 -C.sub.4)alkyl group, a dichlorophenoxy-(C.sub.1 -C.sub.4)alkyl group, a phenylthio-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.1 -C.sub.4)alkylamino-(C.sub.1 -C.sub.4)alkyl group, a di-(C.sub.1 -C.sub.4)alkylamino-(C.sub.1 -C.sub.4)alkyl group, a pyrrolyl-(C.sub.1 -C.sub.4)alkyl group, a chloro-(C.sub.1 -C.sub.4)alkyl group, a cyano-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.1 -C.sub.4)alkoxycarbonyl-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.1 -C.sub.4)alkylthiocarbonyl-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.1 -C.sub.4)alkylcarbonyl-(C.sub.1 -C.sub.4)alkyl group, a phenylcarbonyl-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.5 -C.sub.6)cycloalkyl group, benzyl group, a chlorobenzyl group, a dichlorobenzyl group, a fluorobenzyl group, a methylbenzyl group, a dimethylbenzyl group, a methylbenzylethyl group, naphthyl group, furfuryl group, phenyl group, a chlorophenyl group, a dichlorophenyl group, a cyanophenyl group, a nitrophenyl group, a (C.sub.1 -C.sub.4)alkylphenyl group, a (C.sub.1 -C.sub.4)alkylcarbonyl group, or benzoyl group,
X is an oxygen atom or a sulfur atom;
Y' is a (C.sub.1 -C.sub.4)alkylene group or a (C.sub.2 -C.sub.4)alkenylene group; and
Z is a hydrogen atom, a (C.sub.1 -C.sub.6)alkyl group, a (C.sub.1 -C.sub.4)alkoxy-(C.sub.1 -C.sub.4)alkyl group, a cyano-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.2 -C.sub.4)alkenyl group, phenyl group, a chlorophenyl group, a dichlorophenyl group, a methylphenyl group, a trifluoromethylphenyl group, a nitrophenyl group, benzyl group, a chlorobenzyl group or a dichlorobenzyl group; and a salt of said imidazole derivative.

### Claim 3 (depends on 1)

An imidazole derivative as claimed in claim 1 which is of the formula ##STR252## wherein R.sub.5 is phenyl group, a chlorophenyl group, a bromophenyl group, a nitrophenyl group, a trifluoromethylphenyl group, a dichlorophenyl group, a bromochlorophenyl group, a chlorofluorophenyl group, a trifluoromethylchlorophenyl group, a trichlorophenyl group, a dichlorodimethylphenyl group, a trichloro-dimethylphenyl group, a chloro-methoxyphenyl group, a chloro-methylphenyl group, a (C.sub.1 -C.sub.4)alkylphenyl group, a di-(C.sub.1 -C.sub.4)alkylphenyl group, a (C.sub.2 -C.sub.4)alkenyloxyphenyl group, a (C.sub.1 -C.sub.4)alkoxyphenyl group, a di-(C.sub.1 -C.sub.4)alkoxyphenyl group, a methylsulfonylphenyl group, an acetylphenyl group, a phenoxyphenyl group, or a nitrophenylthiophenyl group;
R.sub.6 is a (C.sub.1 -C.sub.10)alkyl group, a (C.sub.2 -C.sub.4)alkenyl group, a (C.sub.1 -C.sub.4)alkoxy-(C.sub.1 -C.sub.4)alkyl group, a methylthio-(C.sub.1 -C.sub.4)alkyl group, a dichlorophenoxy-(C.sub.1 -C.sub.4)alkyl group, a phenylthio-(C.sub.1 -C.sub.4)alkyl group, cyclohexyl group, an ethoxycarbonyl-(C.sub.1 -C.sub.4)alkyl group, benzyl group, a chlorobenzyl group, a dichlorobenzyl group, naphthyl group, furfuryl group, phenyl group, a chlorophenyl group, a dichlorophenyl group, a cyanophenyl group, a nitrophenyl group, or a (C.sub.1 -C.sub.4)alkylphenyl group,
Y" is a linear (C.sub.2 -C.sub.4)alkylene group,
Z' is a hydrogen atom, a (C.sub.1 -C.sub.6)alkyl group, a (C.sub.2 -C.sub.4)alkenyl group, phenyl group, a chlorophenyl group, a dichlorophenyl group, a methylphenyl group, a nitrophenyl group, or benzyl group, and a salt of said imidazole derivative.

### Claim 4 (depends on 1)

An imidazole derivative as claimed in claim 1 which is of the formula ##STR253## wherein R.sub.7 is phenyl group, a chlorophenyl group, a fluorophenyl group, a bromophenyl group, or nitrophenyl group, a cyanophenyl group, a trifluoromethylphenyl group, a dichlorophenyl group, a dibromophenyl group, a bromochlorophenyl group, a chlorofluorophenyl group, a trifluoromethyl-chlorophenyl group, a trichlorophenyl group, a dichloro-dimethylphenyl group, a trichloro-dimethylphenyl group, a chloro-methoxyphenyl group, a chloro-methylphenyl group, a (C.sub.1 -C.sub.4)alkylphenyl group, a di-(C.sub.1 -C.sub.4)alkylphenyl group, a (C.sub.2 -C.sub.4)alkenyphenyl group, a (C.sub.1 -C.sub.4)alkoxyphenyl group, a di-(C.sub.1 -C.sub.4)alkoxyphenyl group, a methylthiophenyl group, a methylsulfinylphenyl group, a methylsulfonylphenyl group, an acetylphenyl group, diphenyl group, a phenoxyphenyl group, a chlorophenoxyphenyl group, a phenylthiophenyl group or a methylphenylthiophenyl group;
R.sub.8 is a (C.sub.1 -C.sub.10)alkyl group, a (C.sub.2 -C.sub.4)alkenyl group, a (C.sub.2 -C.sub.4)alkynyl group, a (C.sub.1 -C.sub.4)alkoxy-(C.sub.1 -C.sub.4)alkyl group, a methylthio-(C.sub.1 -C.sub.4)alkyl group, a phenoxy-(C.sub.1 -C.sub.4)alkyl group, a phenylthio-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.1 -C.sub.4)alkylamino-(C.sub.1 -C.sub.4)alkyl group, a pyrrolyl-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.1 -C.sub.4)alkylcarbonyl group, a (C.sub.5 -C.sub.6)cycloalkyl group, a chloro(C.sub.1 -C.sub.4)alkyl group, a cyano-(C.sub.1 -C.sub.4)alkyl group, a (C.sub.1 -C.sub.4)alkylthiocarbonyl-(C.sub.1 -C.sub.4)alkyl group, benzyl group, a chlorobenzyl group, a fluorobenzyl group, a dichlorobenzyl group, a methylbenzyl group, a methylbenzylethyl group, an acetyl-(C.sub.1 -C.sub.4)alkyl group, benzoyl group, a phenylcarbonyl-(C.sub.1 -C.sub.4)alkyl group or phenyl group;
Y"' is a linear (C.sub.1 -C.sub.4)alkylene group or a linear (C.sub.2 -C.sub.4)alkenylene group; and
Z" is a hydrogen atom, a (C.sub.1 -C.sub.6)alkyl group, a (C.sub.1 -C.sub.4)alkoxy-(C.sub.1 -C.sub.4)alkyl group, a cyano-(C.sub.1 -C.sub.4)alkyl, a (C.sub.2 -C.sub.4)alkenyl, phenyl group, a chlorophenyl group, a dichlorophenyl group, a methylphenyl group, benzyl group, a chlorobenzyl group or a dichlorobenzyl group; and a salt of said imidazole derivative.

### Claim 5 (depends on 1)

An imidazole derivative as claimed in claim 1 which is of the formula ##STR254## wherein R.sub.9 is a (C.sub.1 -C.sub.4)alkyl group, a phenyl-(C.sub.1 -C.sub.4)alkyl group or a chloro-(C.sub.1 -C.sub.4)alkyl group; and
Y"" is a linear or branched (C.sub.1 -C.sub.4)alkylene group, and a salt of the said imidazole derivative.

### Claim 6 (depends on 1)

An imidazole derivative as claimed in claim 1 which is of the formula ##STR255## wherein R.sub.10 is a (C.sub.5 -C.sub.6)cycloalkyl group or a (C.sub.1 -C.sub.4)alkyl group which is unsubstituted or substituted with phenyl group, a dichlorophenyl group, a (C.sub.2 -C.sub.4)alkenyl group, a (C.sub.1 -C.sub.4)alkoxy group or phenylthio group;
R.sub.11 is furfuryl or (C.sub.1 -C.sub.4)alkyl group which is unsubstituted or substituted with phenyl group, a di-(C.sub.1 -C.sub.4)alkylamino group or a (C.sub.5 -C.sub.6)cycloalkyl group;
Y""' is a (C.sub.1 -C.sub.4)alkylene group; and
Z"' is a hydrogen atom, a (C.sub.1 -C.sub.6)alkyl group, a chlorobenzyl group or a trifluoromethylphenyl group; and a salt of said imidazole derivative.

### Claim 7 (depends on 1)

An imidazole derivative as claimed in claim 1, which is the compound of the formula ##STR256##

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 1)

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