JPH04261133A - New aromatic alkane derivative, its production and insecticide and acaricide containing the same as active ingredient - Google Patents

Abstract

PURPOSE:To obtain a new aromatic alkane derivative, not only excellent in insecticidal and acaricidal activity but also having low toxicity to warm-blooded animals and fishes and useful as an agricultural chemical having high safety. CONSTITUTION:A compound, e.g. 1-(3-phenoxyphenyl)-4-(4-methoxyphenyl)-4- methylpentane expressed by formula I (Ar is substitutable phenyl or substitutable naphthyl; R<1> is methyl, ethyl or isopropyl; R<2> is H or methyl; R<1> and R<2>, together with C to which they are bound, may form a substitutable cycloalkyl; R<3> is backbone radical of an alcohol normally used in the form of R<3> OH in the case of natural or synthetic pyrethroid). The aforementioned compound is obtained by reacting, e.g. a ketone expressed by formula II with an aldehyde expressed by formula III (R<12> is backbone radical of an alcohol normally used in the form of R<12> CH2OH in the case of the synthetic pyrethroid) and reducing the resultant alpha,beta-unsaturated carbonyl compound expressed by formula IV.

Description

[Detailed description of the invention]

0001

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel aromatic alkane derivative, a method for producing the same, and insecticides and acaricides containing the same as an active ingredient.

The present invention relates to a novel compound, an aromatic alkane derivative represented by the general formula (I) shown below.

0003

embedded image (wherein, Ar represents an optionally substituted phenyl group or naphthyl group, R1 represents a methyl group, ethyl group or isopropyl group, R2 represents a hydrogen atom or a methyl group, R1 and R2 together with the carbon atom to which they are attached may form an optionally substituted cycloalkyl group; R3 represents the alcoholic radical customarily used in the form R3OH in the case of natural and synthetic pyrethroids)

The general formula (I) includes various possible optical isomers as well as mixtures of these isomer components.

The present invention also provides a method for producing a compound of the general formula (I), which is a compound of the general formula (I) shown below.
VII)

[0006]

embedded image (wherein Ar, R1 and R2 have the above meanings)
and the general formula (VIII
)

[0007]

[Chemical formula 24] (Here, R12 is R12CH in the case of a synthetic pyrethroid.
represents the alcoholic radical commonly used in the form 2OH)
The general formula (IX) represented by the following chemical formula 25 obtained by reacting with the aldehyde represented by

[0008]

[Image Omitted] The α,β-unsaturated carbonyl compound represented by the above general formula (I) is reduced: It also relates to a method for producing the compound.

[0009] The present invention also provides a method for producing a compound of general formula (I), wherein the compound of general formula (I) is
X)

0010

embedded image (wherein Ar, R1 and R2 have the above meanings)
and the general formula (XI) represented by the following chemical formula 27

[0011]

embedded image (wherein, R12 is R12CH in the case of a synthetic pyrethroid)
represents the alcoholic radical commonly used in the form 2OH)
The following chemical formula 28 obtained by reacting with the ketone represented by
General formula (XII) represented by

0012

It also relates to a method characterized in that it reduces an α,β-unsaturated carbonyl compound represented by the formula (wherein Ar, R1, R2 and R12 have the abovementioned meanings).

The present invention also provides a method for producing a compound of general formula (I), which is represented by the following general formula (29).
XIII)

[0014]

embedded image (wherein Ar, R1 and R2 have the above meanings)
An aldehyde represented by and the following chemical formula 30 or chemical formula 31
General formula (XIV) or (XV) represented by

0015
]

[C30]

[0016]

embedded image (wherein R3 and R12 represent the above meanings, R1
3 represents an alkyl group or a phenyl group, and R14 represents an alkyl group, respectively) to obtain a compound represented by the following general formula (X
VI) or (XVII)

[0017]

[C32]

[0018]

It also relates to a method characterized in that it reduces an olefin represented by the formula: ##STR33## in which Ar, R1, R2, R12 and R3 have the meanings given above.

The present invention also relates to insecticidal and acaricidal compositions containing the aromatic alkane derivative of general formula (I) as an active ingredient.

[0020]

[Prior Art] Conventionally, agricultural and horticultural or epidemic prevention insecticides include organochlorine insecticides such as DDT and BHC, organophosphorus insecticides such as parathion and malathion, and carbamate insecticides such as carbaryl and methomyl. Many have been developed,
It has been used in large quantities to control agricultural, horticultural and sanitary pests, and has greatly contributed to the prevention of agricultural crops.

However, in recent years, the use of these insecticides has been studied from the viewpoint of pollution problems such as environmental contamination, and safety such as residual and accumulation. In addition, some of these products have developed resistant pests due to long-term use.

[0022] With the above points in mind, pyrethroid compounds have been developed, focusing on the fact that they generally have low toxicity, are easily degradable in the environment, have little persistence, and furthermore, their decomposition products are non-toxic. It has been put into practical use. However, the pyrethroid compounds that have already been put into practical use have the drawback of high toxicity to fish. Although pyrethroids with low fish toxicity have been studied and reported, there is an undeniable tendency for insecticidal activity to decrease as fish toxicity safety increases.

[0023]

SUMMARY OF THE INVENTION The present invention has been made to solve the problems of the prior art.

[0024]

[Means for Solving the Problems] The present inventors have conducted extensive research with the aim of developing insecticides and acaricides that overcome these drawbacks and are highly safe for warm-blooded animals and fish. General formula (I) represented by the following chemical formula (34)

[0025]

A novel aromatic alkane derivative represented by the formula (wherein Ar, R1, R2 and R3 have the above meanings) is safe to warm-blooded animals, has low toxicity to fish, and has high insecticidal properties. ,
It was discovered that it has acaricidal activity, and the present invention was completed.

Conventional pyrethroid compounds have the following chemical formula 3:
General formula (A) represented by 5

[0027]

Cyclopropanecarboxylic acid esters represented by the following formula (35) are common, and various conversions of each segment have been attempted to convert cyclopropanecarboxylic acid into the general formula (36) shown below.
B)

[0028]

It has been found that substituted acetic acid of [Chemical formula 36] shows high insecticidal activity (M. Elliott et al.,
Chem. Soc. Reviews, 1
978,473, Japanese Unexamined Patent Publication No. 49-26425, 4
9-126826). Various attempts have been made to convert the ester bond, but in recent years, the oxime ether bond has been converted to the general formula (C) shown by the following chemical formula (C).

[0029]

It has been reported that the compound represented by the following formula shows high insecticidal activity. (JP-A-53-103449, JP-A-54-141740, JP-A-54-138532)
Publication No.). Furthermore, the general formula (D
)

[0030]

It has been reported that a compound having an ether bond represented by the following formula shows high insecticidal activity (West German Published Patent Application No.
Publication No. 7510).

The compound of the present invention has a previously unknown -CH2CH2- bond in place of the ester bond -COO-, and has the general formula (I) shown by the following chemical formula 39.

0032
]

It is represented by the following formula (wherein Ar, R1, R2, and R3 have the above meanings), and has an active structure different from that of conventional pesticides, and has low toxicity, especially to warm-blooded animals and fish. high insecticide,
Has acaricidal activity.

In the compound of general formula (I), a group represented by the following formula 40

[0034]

embedded image is an important active structure element. Ar represents an optionally substituted phenyl group or naphthyl group. Substituents include halogen atoms, nitro groups, cyano groups, optionally substituted lower alkyl, alkenyl, alkynyl, cycloalkyl, aryl, lower alkoxy, alkenyloxy, alkynyloxy, alkylthio, cycloalkyloxy, aryloxy, and lower acyl. , alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, methylenedioxy, ethylenedioxy group, or polymethylene group having 3 to 5 carbon atoms. More specifically, lower haloalkyl group, alkoxyalkyl group, haloalkoxyalkyl group, alkylthioalkyl group, haloalkylthio group, haloalkoxy group,
Alkoxyalkoxy group, haloalkoxyalkoxy group, alkenyloxyalkoxy group, haloalkenyloxy group, haloalkynyloxy group, alkoxyalkylthio group, alkylthioalkoxy group, alkylthioalkylthio group, haloacyl group, haloalkoxycarbonyl group, haloalkenyloxycarbonyl group, 3,4-difluoromethylenedioxy group, 3,4-trifluoroethylenedioxy group, etc. Industrially preferred are mono- or polysubstituted phenyl groups having the same or different substituents.

Specific examples of the Ar group are shown below, but the invention is not limited to these examples. That is, phenyl group, 4-methylphenyl group, 3,4-dimethylphenyl group, 4-trifluoromethylphenyl group, 3-methylphenyl group,
3-trifluoromethylphenyl group, 4-chlorophenyl group, 3,4-dichlorophenyl group, 4-nitrophenyl group, 4-methylthiophenyl group, 4-methoxyphenyl group, 3,4-dimethoxyphenyl group, 3,4- Methylenedioxyphenyl group, 4-difluoromethylthiophenyl group, 4-trifluoromethylthiophenyl group, 3,
4-difluoromethylenedioxyphenyl group, 4-cyanophenyl group, 4-fluorophenyl group, 4-bromophenyl group, 3,4-difluorophenyl group, 3,4-dibromophenyl group, 4-chloro-3-fluoro Phenyl group, 3-chloro-4-fluorophenyl group, 3-chloro-4-methylphenyl group, 3-bromo-4-chlorophenyl group, 4-difluoromethoxyphenyl group, 3,4-
Bis(difluoromethoxy)phenyl group, 4-trifluoromethoxyphenyl group, 3,4-bis(trifluoromethoxy)phenyl group, 4-methoxy-3,5-dimethylphenyl group, 3,4-trifluoroethylenedioxy Phenyl group, 4-tert-butylphenyl group, 4-
Ethylphenyl group, 4-isopropylphenyl group, 3,
4-difluoroethylenedioxyphenyl group, 4-isopropenylphenyl group, 4-vinylphenyl group, 4-(
2,2-dichlorovinyl)phenyl group, 4-chloro-3
-methylphenyl group, 3-bromo-4-fluorophenyl group, 2-naphthyl group, 3-fluoro-4-bromophenyl group, 4-fluoro-3-methylphenyl group, 3-fluoro-4-methylphenyl group, 3-bromo-4-methylphenyl group, 3,4-diethylphenyl group, 3,4-
Diisopropylphenyl group, 3-ethyl-4-methylphenyl group, 4-isopropyl-3-methylphenyl group,
4-methylsulfinylphenyl group, 4-allylphenyl group, 4-acetylphenyl group, 4-ethoxycarbonylphenyl group, 4-ethoxyphenyl group, 1,2,3,
4-tetrahydronaphthalen-7-yl group, 3,5-dichloro-4-
Methylphenyl group, indan-5-yl group, 4-propargylphenyl group, 3-methoxy-4-methylphenyl group, 4-methoxymethylphenyl group, 4-(1-chloroethylene-1-yl)phenyl group, 4 -(2-chloroallyl)phenyl group, 4-isobutyryl phenyl group, 4-
Methoxycarbonylphenyl group, 3-nitro-4,5-
Dimethylphenyl group, 3-ethoxy-4-bromophenyl group, 3-chloro-4-methoxyphenyl group, 4-bromo-3-chlorophenyl group, 3,4-(di-tert-butyl)phenyl group, 4-ethyl -3-methylphenyl group, 4-tert-butyl-3-methylphenyl group, 4-(1,1,2,2-tetrafluoroethoxy)phenyl group, 4-(2,2-dichlorovinyloxy)phenyl group , 4-(2,2,2-trifluoroethoxy)phenyl group, 4-pentafluoroethoxyphenyl group, 4
-(chlorodifluoromethoxy)phenyl group, 4-(chlorofluoromethoxy)phenyl group, 4-(dichlorofluoromethoxy)phenyl group, 4-(1,1-difluoroethoxy)phenyl group, 4-(1,2,2 -trichloro-1,2-difluoroethoxy)phenyl group, 4-(
2-bromo-1,1,2,2-tetrafluoroethoxy)phenyl group, 4-(2-propynyloxy)phenyl group, 4-(1-propynyloxy)phenyl group, 4-allyloxyphenyl group, 4- Ethynyloxyphenyl group, 4-(2-chloroethynyl)phenyl group, 4-(n
-propoxy) phenyl group, 4-isopropoxyphenyl group, 4-cyclopentyloxyphenyl group, 4-(
n-amyloxy) phenyl group, 4-isobutoxyphenyl group, 4-iodophenyl group, 4-vinyloxyphenyl group, 4-biphenyl group, 4-(n-butoxy)
Phenyl group, 4-(sec-butoxy)phenyl group, 6
-Methyl-2-naphthyl group, 4-phenoxyphenyl group, 4-(2-fluoroethoxycarbonyl)phenyl group, 4-(1,1,2,2-tetrafluoroethoxycarbonyl)phenyl group, 4-(2- iodo-1,1-difluoroethoxy)phenyl group, 4-cyclohexyloxyphenyl group, 3-chloro-4-ethoxyphenyl group,
4-formylphenyl group, 4-ethoxymethylphenyl group, 4-trifluoroacetyloxyphenyl group, 4-
(1-ethoxyethyl)phenyl group, 4-(1-methoxyethyl)phenyl group, 4-ethoxy-3-methylphenyl group, 4-(2-methylpropenyl)phenyl group, 4
-(1,2,2-trichlorovinyloxy)phenyl group,
3,4-diethoxyphenyl group, 4-ethynylphenyl group, 4-ethoxy3,5-dimethylphenyl group, 4-ethoxy-3-methoxyphenyl group, 4-ethylthiophenyl group, 4-(2,2, 2-trifluoroethoxycarbonyl) phenyl group, 4-(2-chloroethoxy) phenyl group, 4-(1-ethylvinyl) phenyl group, 4-(
1-methyl-1-propenyl) phenyl group, 4-methoxymethylthiophenyl group, 4-(1,2-dichlorovinyloxy) phenyl group, 4-(2,3-dichloroallyloxy) phenyl group, 4-(2 -iodo-1-fluorovinyloxy) phenyl group, 4-(2-fluoroethoxy) phenyl group, 4-(2-chloro-1,1-difluoroethoxy) phenyl group, 4-(2-chloro-1-fluoro vinyloxy) phenyl group, 4-isopropylthiophenyl group, 4-(2,2-dichloro-1,1-difluoroethoxy) phenyl group, 4-(2,2-dichloro-1-fluorovinyloxy) phenyl group, 4-(1,1,2,2-
tetrafluoroethoxy) phenyl group, 3-chloro-4
-Ethoxyphenyl group, 4-(tetrahydro-3-furyloxy)phenyl group, 4-ethylthio group, 3-ethoxyphenyl group, 4-allyloxyphenyl group, 4-methoxymethylthiophenyl group, 4-(2,2- Examples include dichlorovinyloxy) phenyl group, 4-(1,1,1-trifluoroethoxy) phenyl group, and the like.

R1 is a methyl group, an ethyl group or an isopropyl group, preferably a methyl group or an ethyl group. R2 is a hydrogen atom or a methyl group, preferably a methyl group. R1 and R2 together with the carbon atom to which they are attached may form an optionally substituted cycloalkyl group. A cycloalkyl group having 3 to 6 carbon atoms is preferable, and a halogen or methyl group is preferable as a substituent.

The group R3, in the form R3OH, is the "alcohol moiety" known in natural and synthetic pyrethroids.
This corresponds to

Examples of R3 include groups (II), (III), (IV), and (V) represented by the following formulas 41, 42, 43, and 44.

[0039]

[C41]

[0040]

[C42]

[0041]

[C43]

[0042]

[C44]

Here, R4 is a hydrogen atom, an ethynyl group or a cyano group, and R5 is an allyl group, a propargyl group,
benzyl, thenyl, furylmethyl, phenoxy, phenylmercapto, benzoyl or pyridyloxy groups, optionally substituted with halogen, alkyl, alkoxy, haloalkyl, cyano or nitro; R6 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a haloalkyl group, a cyano group, or a nitro group, and n is an integer of 1 to 4, and n is 2 or more. , R6 is each independently selected from each other, A represents an oxygen atom, a sulfur atom or -CH=CH-, R7 represents a hydrogen atom, a methyl group, an alkoxy group or a halogen atom, and R8 represents a phthalimide R9 represents an alkyl group, an alkenyl group, an alkynyl group or an aralkyl group; , R
10 represents a hydrogen atom or a methyl group.

Preferred examples of the group R3 include 5-benzyl-3-furylmethyl group, 3-phenoxybenzyl group, 3
-(4-fluorophenoxy)benzyl group, 3-(4-
Bromophenoxy)benzyl group, 3-(4-chlorophenoxy)benzyl group, 3-(3-fluorophenoxy)
Benzyl group, 3-(2-bromophenoxy)benzyl group, 3-(3-chlorophenoxy)benzyl group, 3-(4
-methylphenoxy)benzyl group, 3-(2-fluorophenoxy)benzyl group, 3-(2-chlorophenoxy)benzyl group, 3-(3-bromophenoxy)benzyl group, 3-(3-methoxyphenoxy)benzyl group , 3-
(2-methylphenoxy)benzyl group, 3-(4-ethoxyphenoxy)benzyl group, 3-(4-methoxyphenoxy)benzyl group, 3-(3-methylphenoxy)benzyl group, 3-(2-methoxyphenoxy) Benzyl group, 3-phenylthiobenzyl group, 3-benzoylbenzyl group, 3-benzylbenzyl group, 3-(4-chlorobenzyl)benzyl group, 3-(4-fluorobenzyl)benzyl group, 3-(3,5 -dichlorophenoxy)benzyl group, 3-(3,4-dichlorophenoxy)benzyl group,
3-(4-chloro-2-methylphenoxy)benzyl group, 3-(2-chloro-5-methylphenoxy)benzyl group, 3-(4-chloro-3-methylphenoxy)benzyl group, 3-(4- ethylphenoxy)benzyl group, 3-
(3-chloro-5-methoxyphenoxy)benzyl group,
3-(4-fluorophenylthio)benzyl group, 3-(
3-fluorophenylthio)benzyl group, 3-(3,5
-dichlorobenzoyl)benzyl group, 3-(3,4-dichlorobenzoyl)benzyl group, 3-(2,5-dichlorobenzoyl)benzyl group, 3-(4-methylbenzyl)benzyl group, 3-(4-iso propoxyphenoxy)
Benzyl group, 3-phenoxy-4-fluorobenzyl group, 3-phenoxy-4-chlorobenzyl group, 3-phenoxy-4-bromobenzyl group, 3-(4-fluorophenoxy)-4-fluorobenzyl group, 3- (4-bromophenoxy)-4-fluorobenzyl group, 3-(4-chlorophenoxy)-4-fluorobenzyl group, 3-(3
-bromophenoxy)-4-fluorobenzyl group, 3-
(3-chlorophenoxy)-4-fluorobenzyl group,
3-(4-methylphenoxy)-4-fluorobenzyl group, 3-(4-methoxyphenoxy)-4-fluorobenzyl group, 3-(2-fluorophenoxy)-4-fluorobenzyl group, 3-phenoxy-5 -Methoxybenzyl group, 3-(3-methoxyphenoxy)-4-fluorobenzyl group, 3-phenoxy-2-fluorobenzyl group, 3-(4-fluorophenoxy)-2-fluorobenzyl group, 3-(3- fluorophenoxy)-2-fluorobenzyl group, 3-(2-fluorophenoxy)-2-
Fluorobenzyl group, 3-(4-fluorophenoxy)
-5-fluorobenzyl group, 3-(3-fluorophenoxy)-4-fluorobenzyl group, 3-(3-fluorophenoxy)-5-fluorobenzyl group, 3-(2-fluorophenoxy)-5-fluorobenzyl group, 3-phenoxy-4-methylbenzyl group, 3-(4-methylphenoxy)-5-fluorobenzyl group, 3-(3-methoxyphenoxy)-5-fluorobenzyl group, 3-(2
-fluorophenoxy)-6-fluorobenzyl group, 3
-(3-fluorophenoxy)-6-fluorobenzyl group, 3-(4-fluorophenoxy)-6-fluorobenzyl group, 3-phenoxy-2-fluorobenzyl group,
3-phenoxy-5-fluorobenzyl group, 3-phenoxy-6-fluorobenzyl group, 3-phenoxy-6-
Chlorobenzyl group, 3-phenoxy-5-fluorobenzyl group, 3-phenoxy-2-chlorobenzyl group, 3-
(3-methylphenoxy)-4-chlorobenzyl group, 3
-(4-fluorophenoxy)-4-chlorobenzyl group, 3-phenoxy-5-chlorobenzyl group, 3-phenoxy-6-bromobenzyl group, 3-phenoxy-4-bromobenzyl group, 3-phenoxy-5- Bromobenzyl group, 3-(4-ethoxyphenoxy)-4-fluorobenzyl group, phthalimidomethyl group, 3,4,5,6-tetrahydrophthalimidomethyl group, 6-phenoxy-2
-pyridylmethyl group, 6-(4-fluorophenoxy)
-2-pyridylmethyl group, 6-(4-chlorophenoxy)-2-pyridylmethyl group, 6-(4-bromophenoxy)-2-pyridylmethyl group, 6-(4-methylphenoxy)-2-pyridylmethyl group, 6-(3-fluorophenoxy)-2-pyridylmethyl group, 6-(2-fluorophenoxy)-2-pyridylmethyl group, 6-(2-chlorophenoxy)-2-pyridylmethyl group, 6-( 2-
Bromophenoxy)-2-pyridylmethyl group, 6-(3
-chlorophenoxy)-2-pyridylmethyl group, 6-(
3-bromophenoxy)-2-pyridylmethyl group, 6-
(4-ethoxyphenoxy)-2-pyridylmethyl group,
6-(4-methoxyphenoxy)-2-pyridylmethyl group, 6-(3-methoxyphenoxy)-2-pyridylmethyl group, 3-(2-pyridyloxy)benzyl group, 3-
(3-pyridyloxy)benzyl group, 3-(2-pyridyloxy)-4-fluorobenzyl group, 3-(3-pyridyloxy)-4-fluorobenzyl group, 3-(2-pyridyloxy)-4- Chlorobenzyl group, 3-(2-pyridyloxy)-4-methylbenzyl group, 3-(2-pyridyloxy)-4-bromobenzyl group, 3-(3-pyridyloxy)-4-chlorobenzyl group, 3 -(3-pyridyloxy)-4-bromobenzyl group, 3-(3-pyridyloxy)-4-methylbenzyl group, 3-phenoxy-4-trifluoromethylbenzyl group, 3-phenoxy-α-cyano-benzyl group group, 3-phenoxy-α-ethynyl-benzyl group, 3-(4-fluorophenoxy)
-α-cyano-benzyl group, 3-(4-fluorophenoxy)-α-ethynyl-benzyl group, 3-(4-bromophenoxy)-α-cyano-benzyl group, 3-(4-bromophenoxy)-α -ethynyl-benzyl group, 3-(
4-chlorophenoxy)-α-cyano-benzyl group, 3
-(4-chlorophenoxy)-α-ethynyl-benzyl group, 3-(3-fluorophenoxy)-α-cyano-benzyl group, 3-(3-fluorophenoxy)-α-ethynyl-benzyl group, 3-( 2-bromophenoxy)-α
-cyano-benzyl group, 3-(2-bromophenoxy)
-α-ethynyl-benzyl group, 3-(3-chlorophenoxy)-α-cyano-benzyl group, 3-(3-chlorophenoxy)-α-ethynyl-benzyl group, 3-(4-methylphenoxy)-α -cyano-benzyl group, 3-(4
-methylphenoxy)-α-ethynyl-benzyl group, 3
-(4-ethoxyphenoxy)-α-cyano-benzyl group, 3-(4-ethoxyphenoxy)-α-ethynyl-
Benzyl group, 3-(4-methoxyphenoxy)-α-cyano-benzyl group, 3-(4-methoxyphenoxy)-
α-ethynyl-benzyl group, 3-phenylthio-α-cyano-benzyl group, 3-phenylthio-α-ethynyl-
Benzyl group, 3-benzoyl-α-cyano-benzyl group, 3-benzoyl-α-ethynyl-benzyl group, 3-benzyl-α-cyano-benzyl group, 3-benzyl-α-
Ethynyl-benzyl group, 3-(4-chlorobenzyl)-
α-cyano-benzyl group, 3-(4-chlorobenzyl)
-α-ethynyl-benzyl group, 3-(4-fluorobenzyl)-α-cyano-benzyl group, 3-(3,4-dichlorophenoxy)-α-cyano-benzyl group, 3-(4-fluorobenzyl)-α-cyano-benzyl group,
-fluorophenylthio)-α-cyano-benzyl group,
3-(4-fluorophenylthio)-α-ethynyl-benzyl group, 3-phenoxy-4-fluoro-α-cyano-benzyl group, 3-phenoxy-4-fluoro-α-ethynyl-benzyl group, 3-phenoxy -4-chloro-α
-cyano-benzyl group, 3-phenoxy-4-chloro-
α-ethynyl-benzyl group, 3-phenoxy-4-bromo-α-cyano-benzyl group, 3-phenoxy-4-bromo-α-ethynyl-benzyl group, 3-(4-fluorophenoxy)-4-fluoro- α-cyano-benzyl group, 3-(4-fluorophenoxy)-4-fluoro-α
-ethynyl-benzyl group, 3-(4-bromophenoxy)-4-fluoro-α-cyano-benzyl group, 3-(4-bromophenoxy)-4-fluoro-α-cyano-benzyl group,
-bromophenoxy)-4-fluoro-α-ethynyl-
benzyl group, 3-(4-chlorophenoxy)-4-fluoro-α-cyano-benzyl group, 3-(4-chlorophenoxy)-4-fluoro-α-ethynyl-benzyl group,
3-(3-bromophenoxy)-4-fluoro-α-cyano-benzyl group, 3-(3-bromophenoxy)-4
-Fluoro-α-ethynyl-benzyl group, 3-(3-chlorophenoxy)-4-fluoro-α-cyano-benzyl group, 3-(3-chlorophenoxy)-4-fluoro-
α-ethynyl-benzyl group, 3-(4-methylphenoxy)-4-fluoro-α-cyano-benzyl group, 3-(
4-methylphenoxy)-4-fluoro-α-ethynyl-benzyl group, 3-(4-methoxyphenoxy)-4-
Fluoro-α-cyano-benzyl group, 3-(4-methoxyphenoxy)-4-fluoro-α-ethynyl-benzyl group, 3-(2-fluorophenoxy)-4-fluoro-α-cyano-benzyl group, 3 -(2-fluorophenoxy)-4-fluoro-α-ethynyl-benzyl group, 3
-phenoxy-5-methoxy-α-cyano-benzyl group, 3-phenoxy-5-methoxy-α-ethynyl-benzyl group, 3-(3-methoxyphenoxy)-4-fluoro-α-cyano-benzyl group, 3 -(3-methoxyphenoxy)-4-fluoro-α-ethynyl-benzyl group,
3-(3-fluorophenoxy)-4-fluoro-α-
Cyano-benzyl group, 3-(3-fluorophenoxy)
-4-fluoro-α-ethynyl-benzyl group, 3-phenoxy-4-methyl-α-cyano-benzyl group, 3-phenoxy-4-methyl-α-ethynyl-benzyl group, 3
-(3-methylphenoxy)-4-chloro-α-cyano-benzyl group, 3-(3-methylphenoxy)-4-chloro-α-ethynyl-benzyl group, 3-(4-fluorophenoxy)-4- chloro-α-cyano-benzyl group,
3-(4-fluorophenoxy)-4-chloro-α-ethynyl-benzyl group, 3-phenoxy-4-bromo-α
-cyano-benzyl group, 3-phenoxy-4-bromo-
α-ethynyl-benzyl group, 3-(4-ethoxyphenoxy)-4-fluoro-α-cyano-benzyl group, 3-
(4-ethoxyphenoxy)-4-fluoro-α-ethynyl-benzyl group, 6-phenoxy-α-cyano-2-
Pyridylmethyl group, 6-phenoxy-α-ethynyl-2
-pyridylmethyl group, 6-(4-fluorophenoxy)
-α-cyano-4-pyridylmethyl group, 6-(4-fluorophenoxy)-α-ethyl-4-pyridylmethyl group, 6-(4-chlorophenoxy)-α-cyano-2-pyridylmethyl group, 6 -(4-chlorophenoxy)-α-
Ethynyl-2-pyridylmethyl group, 6-(4-bromophenoxy)-α-cyano-2-pyridylmethyl group, 6-
(4-bromophenoxy)-α-ethynyl-2-pyridylmethyl group, 6-(4-methylphenoxy)-α-cyano-2-pyridylmethyl group, 6-(4-methylphenoxy)-α-ethynyl-2 -pyridylmethyl group, 6-(3
-fluorophenoxy)-α-cyano-2-pyridylmethyl group, 6-(3-fluorophenoxy)-α-ethynyl-2-pyridylmethyl group, 6-(2-fluorophenoxy)-α-cyano-2-pyridyl Methyl group, 6-(2
-fluorophenoxy)-α-ethynyl-2-pyridylmethyl group, 6-(2-chlorophenoxy)-α-cyano-2-pyridylmethyl group, 6-(2-chlorophenoxy)-α-ethynyl-2-pyridyl Methyl group, 6-(3-
chlorophenoxy)-α-cyano-2-pyridylmethyl group, 6-(3-chlorophenoxy)-α-ethynyl-2
-pyridylmethyl group, 6-(3-bromophenoxy)-
α-cyano-2-pyridylmethyl group, 6-(3-bromophenoxy)-α-ethynyl-2-pyridylmethyl group,
6-(4-ethoxyphenoxy)-α-cyano-2-pyridylmethyl group, 6-(4-ethoxyphenoxy)-α
-ethynyl-2-pyridylmethyl group, 6-(4-methoxyphenoxy)-α-cyano-2-pyridylmethyl group,
6-(4-methoxyphenoxy)-α-cyano-2-pyridylmethyl group, 6-(4-methoxyphenoxy)-α
-ethynyl-2-pyridylmethyl group, 6-(3-methoxyphenoxy)-α-cyano-2-pyridylmethyl group,
6-(3-methoxyphenoxy)-α-ethynyl-2-
Pyridylmethyl group, 3-(2-pyridyloxy)-α-
Cyano-benzyl group, 3-(2-pyridyloxy)-α
-ethynyl-benzyl group, 3-(3-pyridyloxy)
-α-cyano-benzyl group, 3-(3-pyridyloxy)-α-ethynyl-benzyl group, 3-(2-pyridyloxy)-4-fluoro-α-cyano-benzyl group, 3-
(2-pyridyloxy)-4-fluoro-α-ethynyl-benzyl group, 3-(3-pyridyloxy)-4-fluoro-α-cyano-benzyl group, 3-(3-pyridyloxy)-4-fluoro -α-ethynyl-benzyl group, 3
-(2-pyridyloxy)-4-chloro-α-cyano-
Benzyl group, 3-(2-pyridyloxy)-4-methyl-
α-cyano-benzyl group, 3-(2-pyridyloxy)
-4-methyl-α-ethynyl-benzyl group, 3-(2-
pyridyloxy)-4-bromo-α-cyano-benzyl group, 3-(2-pyridyloxy)-4-bromo-α-ethynyl-benzyl group, 3-(3-pyridyloxy)-4
-chloro-α-cyano-benzyl group, 3-(3-pyridyloxy)-4-chloro-α-ethynyl-benzyl group,
3-(3-pyridyloxy)-4-bromo-α-cyano-benzyl group, 3-(3-pyridyloxy)-4-bromo-α-ethynyl-benzyl group, 3-(3-pyridyloxy)-4 -methyl-α-cyano-benzyl group, 3-(
3-pyridyloxy)-4-methyl-α-ethynyl-benzyl group, 3-phenoxy-4-trifluoromethyl-
α-cyano-benzyl group, 3-phenoxy-4-trifluoromethyl-α-ethynyl-benzyl group, 3-phenylthio-4-fluorobenzyl group, 3-phenylthio-
4-fluoro-α-cyano-benzyl group, 3-phenylthio-4-fluoro-α-ethynyl-benzyl group, 3-
benzyl-4-fluorobenzyl group, 3-benzyl-4
-Fluoro-α-cyano-benzyl group, 3-benzyl-
4-fluoro-α-ethynyl-benzyl group, (2-allyl-3-methylcyclopentenone)-4-yl group, 5-
Examples include propargyl-2-methyl-3-furyl group.

Next, typical examples of the compounds of the present invention will be shown, but of course the compounds of the present invention are not limited to these examples.

1-(3-phenoxyphenyl)-4-(
4-methoxyphenyl)-4-methylpentane, 1-{
3-(4-fluorophenoxy)phenyl}-4-(4
-fluorophenyl)-4-methylhexane, 1-(3
-phenoxyphenyl)-4-(4-methoxyphenyl)-4-methylhexane, 1-{3-(4-fluorophenoxy)phenyl}-4-(4-fluorophenyl)
-4-methylpentane, 1-{3-(4-fluorophenoxy)phenyl}-4-(4-methylphenyl)-4
-Methylpentane, 1-{3-(4-bromophenoxy)phenyl}-4-(4-chlorophenyl)-4-methylpentane, 1-{3-(4-bromophenoxy)phenyl}-4-(4- Chlorophenyl)-4-methylhexane, 1-(3-phenoxyphenyl)-4-phenyl-4-methylpentane, 1-(3-phenoxyphenyl)-4-phenyl-4-methylhexane, 1-(3-phenoxy phenyl)-4-(4-chlorophenyl)-4
-Methylhexane, 1-{3-(4-fluorophenoxy)phenyl}-4-(4-chlorophenyl)-4-methylpentane, 1-{3-(4-fluorophenoxy)
phenyl}-4-(4-ethoxyphenyl)-4-methylpentane, 1-{3-(4-fluorophenoxy)phenyl}-4-(4-chlorophenyl)-4-methylhexane, 1-{3-( 4-fluorophenoxy)phenyl}-4-(3,4-dimethylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(3
,4-dimethylphenyl)-4-methylpentane, 1-
(3-phenoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-methylpentane, 1-{3-
(4-methoxyphenoxy)phenyl}-4-(4-methylthiophenyl)-4-methylpentane, 1-{3-
(3-chlorophenoxy)phenyl}-4-(4-chlorophenyl)-4-methylpentane, 1-{3-(3-
Chlorophenoxy)phenyl}-4-(4-chlorophenyl)-4-methylhexane, 1-{3-(3-fluorophenoxy)phenyl}-4-(4-chlorophenyl)-4-methylpentane, 1-{3 -(3-fluorophenoxy)phenyl}-4-(4-chlorophenyl)-
4-Methylhexane, 1-{3-(4-fluorophenoxy)phenyl}-4-(4-difluoromethoxyphenyl)-4-methylpentane, 1-{3-(4-fluorophenoxy)phenyl}-4- (4-difluoromethoxyphenyl)-4-methylhexane, 1-(5-benzyl-3-furyl)-4-(4-chlorophenyl)-4
-Methylpentane, 1-(5-benzyl-3-furyl)
-4-(4-chlorophenyl)-4-methylhexane,
1-{3-(4-methoxyphenoxy)phenyl}-4
-Phenyl-4-methylpentane, 1-{3-(4-methoxyphenoxy)phenyl}-4-phenyl-4-methylhexane, 1-{3-(2-fluorophenoxy)
phenyl}-4-(4-chlorophenyl)-4-methylpentane, 1-{3-(4-fluorophenoxy)phenyl}-4-(3-chloro-4-methylphenyl)-4
-Methylpentane, 1-(3-phenylthiophenyl)
-4-(4-chlorophenyl)-4-methylpentane,
1-(3-phenoxyphenyl)-4-(4-trifluoromethylthiophenyl)-4-methylpentane, 1-
{3-(4-bromophenoxy)phenyl}-4-(4
-fluorophenyl)-4-methylhexane, 1-{3
-(4-bromophenoxy)phenyl}-4-(4-fluorophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-trifluoromethylphenyl)-4-methylpentane, 1 -(3-phenoxyphenyl)-4-(4-trifluoromethylphenyl)
-4-methylhexane, 1-(3-phenoxyphenyl)-4-(4-trifluoromethylthiophenyl)-4
-Methylpentane, 1-{3-(4-fluorophenoxy)phenyl}-4-(3,4-dichlorophenyl)-
4-methylpentane, 1-{3-(4-fluorophenoxy)phenyl}-4-(3,4-dichlorophenyl)
-4-methylhexane, 1-(3-phenoxyphenyl)-4-(4-difluoromethoxyphenyl)-4-methylpentane, 1-{3-(4-fluorophenoxy)
phenyl}-4-(4-difluoromethylthiophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-difluoromethoxyphenyl)-4-
Methylhexane, 1-(3-phenoxyphenyl)-4
-(3,4-dimethoxyphenyl)-4-methylpentane, 1-{3-(4-chlorophenoxy)phenyl}-
4-(4-cyanophenyl)-4-methylpentane, 1
-{3-(4-fluorophenoxy)phenyl}-4-
(3,4-difluorophenyl)-4-methylhexane, 1-{3-(4-methylphenoxy)phenyl}-4
-(4-chlorophenyl)-4-methylpentane, 1-
{3-(4-methylphenoxy)phenyl}-4-(4
-chlorophenyl)-4-methylhexane, 1-(3-
phenoxyphenyl)-4-(4-chlorophenyl)-
4-Methylpentane, 1-{3-(2-bromophenoxy)phenyl}-4-(3,4-dibromophenyl)-
4-Methylpentane, 1-{3-(2-chlorophenoxy)phenyl}-4-(4-trifluoromethoxyphenyl)-4-methylpentane, 1-{3-(3-methoxyphenoxy)phenyl}-4 -(4-ethylphenyl)-4-methylpentane, 1-{3-(2-methylphenoxy)phenyl}-4-(4-isopropylphenyl)-4-methylpentane, 1-{3-(4-bromo phenoxy)phenyl}-4-(3,4-dichlorophenyl)-4-methylpentane, 1-{3-(4-fluorophenoxy)phenyl}-4-(4-trifluoromethylthiophenyl)-4-methylpentane, 1-{3-(4
-bromophenoxy)phenyl}-4-(3,4-dichlorophenyl)-4-methylhexane, 1-{3-(bromophenoxy)phenyl}-4-(1,2,3,4-
Tetrahydronaphthalen-7-yl)-4-methylpentane, 1-{3-(4-chlorobenzyl)phenyl}-
4-(4-ethoxyphenyl)-4-methylpentane,
1-{3-(3,5-dichlorophenoxy)phenyl}
-4-(indan-5-yl)-4-methylpentane,
1-(3-phenoxyphenyl)-4-(4-difluoromethylthiophenyl)-4-methylpentane, 1-(
3-phenoxyphenyl)-4-(4-ethoxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-ethoxyphenyl)-4-methylhexane, 1-{3-(4 -fluorophenoxy)phenyl}-4-(4-ethoxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-ethoxyphenyl)-4,5-dimethylhexane, 1-(
3-phenoxyphenyl)-4-(4-ethoxyphenyl)-hexane, 1-(3-phenoxyphenyl)-4
-(4-ethoxyphenyl)-5-methylhexane, 1
-{3-(4-fluorophenoxy)phenyl}-4-
(4-ethoxyphenyl)-4-methylhexane, 1-
{3-(4-chlorophenoxy)phenyl}-4-(4
-ethoxyphenyl)-4-methylpentane, 1-{3
-(4-bromophenoxy)phenyl}-4-(4-ethoxyphenyl)-4-methylpentane, 1-{3-(
3-fluorophenoxy)phenyl}-4-(4-ethoxyphenyl)-4-methylpentane, 1-{3-(2
-fluorophenoxy)phenyl}-4-(4-ethoxyphenyl)-4-methylpentane, 1-(3-benzoylphenyl)-4-(4-chlorophenyl)-4-methylpentane, 1-(3-benzoylphenyl) )-4-
(4-ethoxyphenyl)-4-methylpentane, 1-
(3-benzoylphenyl)-4-(4-chlorophenyl)-4-methylhexane, 1-{3-(4-fluorophenoxy)phenyl}-4-(3-trifluoromethylphenyl)-4-methylpentane, 1-{3-(3-
Fluorophenylthio)phenyl}-4-(3-methylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-methylthiophenyl)-4-
Methylpentane, 1-(3-phenoxyphenyl)-4
-(4-methylthiophenyl)-4-methylhexane,
1-(3-phenoxyphenyl)-4-(4-pentafluoroethoxyphenyl)-4-methylpentane, 1-
(3-phenoxyphenyl)-4-(3,4-difluoromethylenedioxyphenyl)-4-methylpentane,
1-{3-(4-fluorophenoxy)phenyl}-4
-(4-pentafluoroethoxyphenyl)-4-methylpentane, 1-{3-(3-chlorophenoxy)phenyl}-4-(4-difluoromethoxyphenyl)-4
-Methylpentane, 1-{3-(3-chlorophenoxy)phenyl}-4-(4-difluoromethoxyphenyl)-4-methylhexane, 1-{3-(3-methyl-4
-chlorophenoxy)phenyl}-4-(4-allylphenyl)-4-methylpentane, 1-{3-(3,5-
dichlorophenoxy)phenyl}-4-(4-tert
-butylphenyl)-4-methylpentane, 1-{3-
(4-chlorophenoxy)phenyl}-4-(3-chloro-4-fluorophenyl)-4-methylpentane, 1
-{3-(3-methylphenoxy)phenyl}-4-(
4-chlorophenyl)-4-methylpentane, 1-{3
-(4-methoxyphenoxy)phenyl}-4-(4-
methoxyphenyl)-4-methylpentane, 1-{3-
(4-fluorobenzyl)phenyl)-4-(4-chlorophenyl)-4-methylpentane, 1-{3-(3,
4-dichlorophenoxy)phenyl}-4-(4-isobutyryl phenyl)-4-methylpentane, 1-{3-
(4-fluorophenoxy)phenyl}-4-phenyl-4-methylpentane, 1-{3-(4-fluorophenoxy)phenyl}-4-phenyl-4-methylpentane, 1-{3-(3-chloro Phenoxy)phenyl}-
4-(3-methylphenyl)-4-methylpentane, 1
-{3-(4-bromophenoxy)phenyl}-4-(
4-difluoromethoxyphenyl)-4-methylpentane, 1-{3-(4-bromophenoxy)phenyl}-
4-(4-difluoromethoxyphenyl)-4-methylhexane, 1-{3-(4-fluorophenoxy)phenyl}-4-(4-tert-butylphenyl)-4-
Methylpentane, 1-(3-phenoxyphenyl)-4
-(2-naphthyl)-4-methylpentane, 1-{3-
(4-fluorophenoxyphenyl}-4-(4-isopropenylphenyl)-4-methylpentane, 1-(3
-phenoxyphenyl)-4-(2-naphthyl)-4-
Methylhexane, 1-{3-(4-fluorophenoxy)phenyl}-4-(4-methoxyphenyl)-4-methylpentane, 1-{3-(4-fluorophenoxy)
phenyl}-4-(4-chloro-3-methylphenyl)
-4-methylpentane, 1-(3-phenoxyphenyl)-4-{3,4-di(trifluoromethoxy)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-(3, 5-dimethyl-4-methoxyphenyl)-4-methylpentane, 1-{3-(4-bromophenoxy)phenyl}-4-(4-methylphenyl)-
4-methylpentane, 1-(3-phenoxyphenyl)
-4-{4-(2,2-dichlorovinyloxy)phenyl}-4-methylpentane, 1-{3-(4-methoxyphenoxy)phenyl}-4-(4-chlorophenyl)-
4-methylpentane, 1-{3-(4-fluorophenylthio)phenyl}-4-(4-chlorophenyl)-4
-Methylpentane, 1-(3-phenoxyphenyl)-
4-{4-(1,1,2,2-tetrafluoroethoxy)phenyl}-4-methylpentane, 1-{3-(4-
Fluorophenoxy)phenyl}-4-(3-methylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-chlorophenyl)-4-methylhexane, 1-(3-phenoxyphenyl) -4-(3
, 4-dichlorophenyl)-4-methylpentane, 1-
(3-phenoxyphenyl)-4-(3,4-dichlorophenyl)-4-methylhexane, 1-(3-phenoxyphenyl)-4-(3-bromo-4-chlorophenyl)-4-methylhexane, 1- (3-phenoxyphenyl)-4-{4-(2,2,2-trifluoroethoxy)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-{4-(2,2, 2-trifluoroethoxy)phenyl}-4-methylhexane, 1-(
3-phenoxyphenyl)-4-{4-(2,2-dichloro-1,1-difluoroethoxy)phenyl}-4-
Methylpentane, 1-(3-phenylthiophenyl)-
4-(4-ethoxyphenyl)-4-methylpentane,
1-(3-phenoxyphenyl)-4-(3-trifluoromethylphenyl-4-methylpentane, 1-(3-
phenoxyphenyl)-4-(3-chloro-4-methoxyphenyl)-4-methylpentane, 1-{3-(4-
methoxyphenoxy)phenyl}-4-(4-bromophenyl)-4-methylpentane, 1-{3-(4-methoxyphenoxy)phenyl}-4-(3,4-diclophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(6-methyl-2-naphthyl)-4-
Methylpentane, 1-{3-(4-fluorophenoxy)phenyl}-4-(3-bromo-4-chlorophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-{4-(2 ,2-dichlorovinyl)phenyl}-4-methylpentane, 1-{3-(4-bromophenoxy)phenyl}-4-(3-trifluoromethylphenyl)-4-methylpentane, 1-(3-phenoxy phenyl)-4-(4-nitrophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4
-nitrophenyl)4-methylhexane, 1-{3-(
4-fluorophenoxy)phenyl}-4-(3-fluoro-4-methylphenyl)-4-methylpentane, 1
-{3-(4-methoxyphenoxy)phenyl}-4-
(4-methylphenyl)-4-methylpentane, 1-{
3-(4-fluorophenoxy)phenyl}-4-(3
, 4-diethylphenyl)-4-methylpentane, 1-
(3-phenoxyphenyl)-4-(4-dichlorofluoromethoxyphenyl)-4-methylpentane, 1-(
3-phenoxyphenyl)-4-(4-methylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-bromophenyl)-4-methylpentane, 1-(3-phenoxyphenyl) )-4-(3-chloro-4-methylphenyl)-4-methylpentane, 1-
(3-phenoxyphenyl)-4-(3,4-dibromophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-tert-butylphenyl)
-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-fluorophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-ethylphenyl)-4-methyl Pentane, 1-(3-phenoxyphenyl)-4-(4-chloro-3-methylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-tert-butylphenyl)-4 −
Methylhexane, 1-(3-phenoxyphenyl)-4
-(3,4-dimethylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(3-chloro-4-methylphenyl)-4-methylhexane, 1-(
3-phenoxyphenyl)-4-(4-methylphenyl)-4-methylhexane, 1-(3-phenoxyphenyl)-4-(3-chloro-4-fluorophenyl)-4
-Methylpentane, 1-(3-phenoxyphenyl)-
4-(3,4-difluorophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(3-bromo-4-fluorophenyl)-4-methylpentane,
1-(3-phenoxyphenyl)-4-(4-bromo-
3-chlorophenyl)-4-methylpentane, 1-(3
-phenoxyphenyl)-4-(3-fluoro-4-methylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(3-bromo-4-methylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(3,4-diethylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-
(4-isopropylphenyl)-4-methylpentane,
1-(3-phenoxyphenyl)-4-(4-isopropylphenyl)-4-methylhexane, 1-(3-phenoxyphenyl)-4-(3,4-diisopropylphenyl)-4-methylpentane, 1- (3-phenoxyphenyl)-4-(3,4-di-tert-butylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(3-ethyl-4-methylphenyl)-4
-Methylpentane, 1-(3-phenoxyphenyl)-
4-(3-methyl-4-tert-butylphenyl)-
4-methylpentane, 1-(3-phenoxyphenyl)
-4-(4-cyanophenyl)-4-methylpentane,
1-(3-phenoxyphenyl)-4-(3,5-dichlorophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-n-propoxyphenyl)-4-methylpentane, 1 -(3-phenoxyphenyl)-4-(4-n-propoxyphenyl)-4-methylhexane, 1-{3-(4-fluorophenoxy)phenyl}-4-(3-chloro-4-fluorophenyl)
-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-isopropoxyphenyl)-4methylpentane, 1-(3-phenoxyphenyl)-4-(4-
isopropoxyphenyl)-4-methylhexane, 1-
(3-phenoxyphenyl)-4-(4-acetylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-cyclopentyloxyphenyl)
-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-cyclopentyloxyphenyl)-4-
Methylhexane, 1-(3-phenoxyphenyl)-4
-(4-n-pentyloxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-
n-pentyloxyphenyl)-4-methylhexane,
1-(3-phenoxyphenyl)-4-(4-isobutyloxyphenyl)-4-methylpentane, 1-(3-
phenoxyphenyl)-4-(4-iodophenyl)-
4-methylpentane, 1-(3-phenoxyphenyl)
-4-(4-iodophenyl)-4-methylhexane,
1-(3-phenoxyphenyl)-4-(4-vinyloxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-biphenyl)-4-methylpentane, 1-(3 -phenoxyphenyl)-4-(4
-n-butoxyphenyl)-4-methylpentane, 1-
(3-phenoxyphenyl)-4-{4-(1-methylpropoxy)phenyl}-4-methylpentane, 1-(
3-phenoxyphenyl)-4-(4-phenoxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-phenoxyphenyl)-4-methylhexane, 1-(3-phenoxyphenyl) )-4-(
4-cyclohexyloxy)-4-methylpentane, 1
-(3-phenoxyphenyl)-4-{4-(1,1-
difluoro-2-iodoethoxy)-phenyl}-4-
Methylpentane, 1-{3-(4-fluorophenoxy)phenyl}-4-(4-isopropylphenyl)-4
-Methylpentane, 1-(3-phenoxyphenyl)-
4-(3-chloro-4-ethoxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(
3-chloro-4-ethoxyphenyl)-4-methylhexane, 1-(3-phenoxyphenyl)-4-{4-(
1-,1-difluoroethoxy)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-(
4-methoxymethylphenyl)-4-methylpentane,
1-(3-phenoxyphenyl)-4-(4-ethoxymethoxyphenyl)-4-methylpentane, 1-(3-
phenoxyphenyl)-4-(4-ethoxymethylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-methoxymethoxyphenyl)-4
-Methylpentane, 1-(3-phenoxyphenyl)-
4-{4-(1-ethoxyethyl)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-
(4-ethoxycarbonylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-{4-(
1-methoxyethyl)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-isopropenylphenyl)-4-methylpentane, 1-(3-
phenoxyphenyl)-4-{4-(2-ethoxyethoxy)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-ethoxy-3-methylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-ethoxy-3-methylphenyl)-4-methylhexane, 1-(3-phenoxyphenyl)-4-{4-(2-methyl-1-propenyl) phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-{4-(1,2,2-trichlorovinyloxy)phenyl}-4-methylpentane, 1-(3-
phenoxyphenyl)-4-{4-(2-chloro-1-
Fluorovinyloxy)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-(3,4-diethoxyphenyl)-4-methylpentane, 1-(3-
phenoxyphenyl)-4-(3,4-diethoxyphenyl)-4-methylhexane, 1-{3-(4-ethoxyphenoxy)phenyl}-4-(4-chlorophenyl)-4-methylpentane, 1- {3-(4-ethoxyphenoxy)phenyl}-4-(4-chlorophenyl)-
4-methylhexane, 1-(3-phenoxyphenyl)
-4-(4-ethynylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-ethoxy-3,5-dimethylphenyl)-4-methylpentane, 1-(3-phenoxy phenyl)-4-(4-propargyloxyphenyl)-4-methylpentane, 1-(
3-phenoxyphenyl)-4-(4-ethoxy-3-
methoxyphenyl)-4-methylpentane, 1-(3-
phenoxyphenyl)-4-(4-ethylthiophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-ethylthiophenyl)-4-methylhexane, 1-{3-(4 -ethoxyphenoxy)phenyl}-4-(4-ethoxyphenyl)-4-methylpentane, 1-{3-(4-ethoxyphenoxy)phenyl}-4-(4-ethoxyphenyl)-4-methylhexane, 1 -(3-phenoxyphenyl)-4-{4-(1
-chlorovinyl)phenyl}-4-methylpentane, 1
-(3-phenoxyphenyl)-4-(4-vinylphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-{4-(2,2,2-trifluoroethoxycarbonyl)phenyl} -4-methylpentane, 1
-(3-phenoxyphenyl)-4-(2-chloroethoxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-{4-(1-ethylvinyl)phenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-{4-(1-methyl-1-propenyl)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-(3-ethoxyphenyl)-4 −
Methylpentane, 1-{4-(4-chlorophenoxy)
phenyl}-4-(3-ethoxyphenyl}-4-methylpentane, 1-{3-(4-bromophenoxy)phenyl}-4-(3-ethoxyphenyl)-4-methylpentane, 1-(3- phenoxyphenyl)-4-(4-
isopropylthiophenyl)-4-methylpentane, 1
-(3-phenoxyphenyl)-4-{4-(1-methoxyiminoethyl)phenyl}-4-methylpentane,
1-{3-(4-isopropoxyphenoxy)phenyl}-4-(4-chlorophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-allyloxyphenyl)-4-methyl Pentane, 1-(3-phenoxyphenyl)-4-{4-(2-methylallyloxy)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-{4-(3-methyl- 2-buten-1-yl)phenyl}-4-methylpentane, 1
-(3-phenoxyphenyl)-4-{4-(2,3-
dichloroallyloxy)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-{4-(2
,2-dichlorovinyloxy)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-{4-
(1-fluoro-2-iodoethyl)phenyl}-4-
Methylpentane, 1-(3-phenoxyphenyl)-4
-{4-(2,2-dicyanovinyl)phenyl}-4-
Methylpentane, 1-(3-phenoxyphenyl)-4
-(4-cyanomethoxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-
trimethylsilyloxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-methoxymethylthiophenyl)-4-methylpentane, 1-
(3-phenoxyphenyl)-4-{4-(2-fluoroethoxy)phenyl)}-4-methylpentane, 1-
(3-phenoxyphenyl)-4-{4-(3-tetrahydrofuryloxy)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4-ethoxyphenyl)-pentane, 1-( 3-phenoxyphenyl)-4-(4-chlorophenyl)-pentane, 1-(
3-phenoxyphenyl)-4-{4-(1,1,2,
2-tetrafluoroethoxy)phenyl}-4-methylhexane, 1-{3-(4-nitrophenoxy)phenyl}-4-(4-chlorophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)- 4-{4-(2
-Chloro-1,1-difluoroethoxy)phenyl}-
4-methylpentane, 1-(3-phenoxyphenyl)
-4-{4-(2,2-dichloro-1,1-difluoroethoxy)phenyl}-4-methylpentane, 1-(3
-phenoxyphenyl)-4-{4-(2,2-dichloro-1-fluoroethoxy)phenyl}-4-methylpentane, 1-(3,4,5,6-tetrahydrophthalimide)-4-(4- ethoxyphenyl)-4-methylpentane, 1-(3-benzoylphenyl)-4-(3-
Bromo-4-ethoxyphenyl)-4-methylpentane, 1-(3-benzylphenyl)-4-(4-chlorophenyl)-4-methylpentane, 1-(3-benzylphenyl)-4-(4-ethoxy phenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4
-chlorophenyl)-5-methylhexane, 1-(3-
phenoxyphenyl)-4-(4-ethoxyphenyl)
-5-methylhexane, 1-(3-phenoxyphenyl)-4-(4-difluoromethoxyphenyl)-5-methylhexane, 1-(6-phenoxy-2-pyridyl)
-4-(4-ethoxyphenyl)-4-methylpentane, 1-(6-phenoxy-2-pyridyl)-4-(4-
chlorophenyl)-4-methylpentane, 1-(6-phenoxy-2-pyridyl)-4-(4-difluoromethoxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(3-chlorophenyl) )-4-
Methylpentane, 1-(3-phenoxyphenyl)-3
-{1-(4-ethoxyphenyl)cyclobutyl}propane, 1-(3-phenoxyphenyl)-4-{4-(
2-chloro-1,1-difluoroethoxy)phenyl}
-4-methylpentane, 1-{6-(4-fluorophenoxy)-2-pyridyl}-4-(4-ethoxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-(4 -chlorophenyl)-4,5-dimethylhexane, 1-(3-phenoxyphenyl)-3-{
1-(4-chlorophenyl)-2,2-dichlorocyclopropyl}-propane, 1-(3-phenoxyphenyl)-3-{1-(4-chlorophenyl)cyclopropyl}-propane, 1-(3-phenoxy phenyl)-3-
{1-(4-ethoxyphenyl)cyclopropyl}-propane, 1-(3-phenoxyphenyl)-3-{1-
(4-ethoxyphenyl)cyclopentyl}-propane, 1-(3-phenoxyphenyl)-3-{1-(4-
ethoxyphenyl)cyclohexyl}-propane, 1-
{4-(2-allyl-3-methylcyclopentene-1-
on)-yl}-3-(4-ethoxyphenyl)-3-
Methylbutane, 1-(5-propargyl-2-methyl-
3-furyl)-4-(4-ethoxyphenyl)-4-methylpentane, 1-{4-(2-allyl-3-methylcyclopenten-1-one)-yl}-3-(4-chlorophenyl)- 3-Methylbutane, 1-(5-propargyl-2-methyl-3-furyl)-4-(4-chlorophenyl)-4-methylpentane, 1-{3-(4-fluorophenoxy)-4-fluorophenyl} -4-(4-
chlorophenyl)-4-methylpentane, 1-{3-(
4-fluorophenoxy)-4-fluorophenyl}-
4-(4-chlorophenyl)-4-methylhexane, 1
-(3-phenoxy-4-fluorophenyl)-4-phenyl-4-methylpentane, 1-(3-phenoxy-
4-chlorophenyl)-4-(4-chlorophenyl)-
4-Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-methoxyphenyl)-4-
Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-chlorophenyl)-pentane,
1-(3-phenoxy-4-fluorophenyl)-4-
(4-chlorophenyl)-4,5-dimethylhexane,
1-(3-phenoxy-4-fluorophenyl)-4-
(3,4-dimethoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4
-(4-ethoxymethylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-
4-(4-methoxymethoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-(1-ethoxyethyl)phenyl}-4
-Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxycarbonylphenyl)-4-methylpentane, 1-(3-phenoxy-4-
Fluorophenyl)-4-{4-(1-methoxyethyl)phenyl}-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-{4-(2-ethoxyethoxy)phenyl}- 4-methylpentane, 1-
(3-phenoxy-4-fluorophenyl)-4-(4
-ethoxy-3-methylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-
4-{4-(2-methyl-1-propenyl)phenyl}
-4-Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-{4-(1,2,2-trichlorovinyloxy)phenyl}-4-methylpentane, 1-
(3-phenoxy-4-fluorophenyl)-4-(3
,4-diethoxyphenyl)-4-methylpentane, 1
-(3-phenoxy-4-fluorophenyl)-4-(
4-ethynylphenyl)-4-methylpentane, 1-(
3-phenoxy-4-fluorophenyl)-4-(4-
Ethoxy-3,5-dimethylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(3,4-dimethylphenyl)-4-methylpentane, 1-{3-( 4-fluorophenoxy)-4-
Fluorophenyl}-4-(4-methoxyphenyl)-
4-Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-chlorophenyl)-hexane, 1-(3-phenoxy-6-chlorophenyl)-4
-(4-chlorophenyl)-4-methylpentane, 1-
(3-phenoxy-4-fluorophenyl)-4-(4
-chlorophenyl)-5-methylhexane, 1-{3-
(4-fluorophenoxy)-4-fluorophenyl}
-4-(3,4-dichlorophenyl)-4-methylhexane, 1-(3-phenoxy-5-methoxyphenyl)
-4-(4-chlorophenyl)-4-methylpentane,
1-{3-(3-chlorophenoxy)-4-fluorophenyl}-4-(4-chlorophenyl)-4-methylpentane, 1-{3-(3-chlorophenoxy)-4-fluorophenyl}-4 -(3,4-dimethylphenyl)
-4-methylhexane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-chlorophenyl)-4-
Methylpentane, 1-{3-(2-fluorophenoxy)-4-fluorophenyl}-4-(3-chloro-4-
Fluorophenyl)-4-methylpentane, 1-{3-
(2-fluorophenoxy)-4-fluorophenyl}
-4-(4-chlorophenyl)-4-methylpentane,
1-{3-(2-fluorophenoxy)-4-fluorophenyl}-4-(4-ethoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(2- naphthyl)-4-methylpentane,
1-(3-phenoxy-4-fluorophenyl)-4-
(4-methoxy-3,5-dimethylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-tert-butylphenyl)-4
-Methylpentane, 1-{3-(4-methoxyphenoxy)-4-fluorophenyl}-4-(4-chlorophenyl)-4-methylpentane, 1-(3-phenoxy-
4-fluorophenyl)-4-(3,4-dimethylphenyl)-4-methylpentane, 1-{3-(4-bromophenoxy)-4-fluorophenyl}-(4-ethoxyphenyl)-4-methyl Pentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-isopropenylphenyl)-hexane, 1-(3-phenoxy-4
-fluorophenoxy)-4-(3-trifluoromethylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-bromophenyl)-4-methylpentane, 1- (3-phenoxy-
4-methylphenyl)-4-(4-chlorophenyl)-
4-Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(3-methylphenyl)-4-methylpentane, 1-(3-phenoxy-5-fluorophenyl)-4-(3, 4-diethylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-{(1,2,3,4-tetrahydronaphthalene)-7-yl}-4-methylpentane, 1-(3
-phenoxy-4-fluorophenyl)-4-(isodan-5-yl)-4-methylpentane, 1-{3-(3
-fluorophenoxy)-4-fluorophenyl}-4
-(4-methoxy-3-methylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(3-bromo-4-ethoxyphenyl)-4
-Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-chlorophenyl)-4-methylhexane, 1-(3-phenoxy-4-fluorophenyl)-4-(3,4- methylenedioxyphenyl)-
4-Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-difluoromethoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4
-fluorophenyl)-4-(4-difluoromethoxyphenyl)-4-methylhexane, 1-{3-(3-methylphenoxy)-4-fluorophenyl)-4-(4
-chlorophenyl)-4-methylpentane, 1-{3-
(3-chlorophenoxy)-5-fluorophenyl)-
4-(3,4-dimethyl-5-nitrophenyl)-4-
Methylpentane, 1-{3-(2-fluorophenoxy)-4-fluorophenyl}-4-(4-methylthiophenyl)-4-methylpentane, 1-{3-(3-fluorophenoxy)-5-fluoro phenyl}-4-(3
-chloro-4-methoxyphenyl)-4-methylpentane, 1-(3-phenoxy-6-bromophenyl)-4
-(4-methylphenyl)-4-methylpentane, 1-
{3-(4-fluorophenoxy)-4-fluorophenyl}-4-(3,4-dichlorophenyl)-4-methylpentane, 1-{3-(4-methylphenoxy)-5
-fluorophenyl}-4-(4-methylsulfinylphenyl)-4-methylpentane, 1-(3-phenoxy-2-fluorophenyl)-4-phenyl-4-methylpentane, 1-(3-phenoxy-4 -fluorophenyl)-4-(4-chlorophenyl)-4,5-dimethylhexane, 1-(3-phenoxy-6-bromophenyl)-4-(4-chlorophenyl)-4-methylpentane, 1-{3 -(4-fluorophenoxy)-2-fluorophenyl)-4-phenyl-4-methylpentane,
1-(3-phenoxy-4-fluorophenyl)-4-
(4-methylthiophenyl)-4-methylpentane, 1
-(3-phenoxy-4-fluorophenyl)-4-(
4-methylphenyl)-4-methylpentane, 1-{3
-(4-fluorophenoxy)-5-fluorophenyl}-4-(4-chlorophenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4
-(4-fluorophenyl)-4-methylpentane, 1
-(3-phenoxy-5-fluorophenyl)-4-(
4-chlorophenyl)-4-methylpentane, 1-(3
-phenoxy-2-fluorophenyl)-4-(4-trifluoromethylphenyl)-4-methylpentane, 1
-(3-phenoxy-4-fluorophenyl)-4-(
4-nitrophenyl)-4-methylpentane, 1-(3
-phenoxy-5-fluorophenyl)-4-(4-chlorophenyl)-4-methylpentane, 1-(3-phenoxy-6-chlorophenyl)-4-(4-methylphenyl)-4-methylpentane, 1- (3-phenoxy-
4-fluorophenyl)-4-(3,4-methylenedioxyphenyl)-4-methylhexane, 1-{3-(3
-chlorophenoxy)-4-fluorophenyl}-4-
(4-chlorophenyl)-hexane, 1-(3-phenoxy-6-fluorophenyl)-4-(4-chlorophenyl)-4-methylpentane, 1-(3-phenoxy-
4-fluorophenyl)-4-(3-chloro-4-methylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-trifluoromethylthiophenyl)-4- Methylpentane, 1-(
3-phenoxy-4-fluorophenyl)-4-(4-
difluoromethoxyphenyl)-hexane, 1-(3-
Phenoxy-4-fluorophenyl)-4-(4-cyanophenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(3,4-difluorophenyl)-4-methylpentane , 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(3,4-dibromophenyl) )-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-trifluoromethoxyphenyl)-4-methylpentane, 1-(3-
Phenoxy-4-fluorophenyl)-4-(4-ethylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-isopropylphenyl)-4-methylpentane, 1 -(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-hexane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-pentafluoroethoxyphenyl)-4-methyl Pentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-difluoromethoxyphenyl)-4,5-dimethylhexane, 1-(3
-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4-methylhexane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-allylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-methoxymethylphenyl)-4-methylpentane, 1-(3-phenoxy-5-chlorophenyl)-4-(4-methylphenyl)- 4-methylpentane, 1-(3-phenoxy-4
-fluorophenyl)-4-(4-isobutyryl phenyl)-4-methylpentane, 1-(3-phenoxy-4
-fluorophenyl)-4-(3,5-dichlorophenyl)-4-methylpentane, 1-(3-phenoxy-4
-fluorophenyl)-4-(3,4-di-tert-
butylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-difluoromethoxyphenyl)-4-methylhexane, 1-(
3-phenoxy-4-fluorophenyl)-4-{3,
4-bis(trifluoromethoxy)phenyl}-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-methoxy-3,5-dimethylphenyl)-4-methylpentane, 1 -(3-phenoxy-
4-fluorophenyl)-4-{4-2,2-dichlorovinyloxy)phenyl}-4-methylpentane, 1-(
3-phenoxy-4-fluorophenyl)-4-(4-
ethoxyphenyl)-4,5-dimethylhexane, 1-
(3-phenoxy-4-fluorophenyl)-4-{4
-(1,1,2,2-tetrafluoroethoxy)phenyl}-4-methylpentane, 1-(3-phenoxy-4
-fluorophenyl)-4-(3-bromo-4-chlorophenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-{4-(2,2,2
-trifluoroethoxy)phenyl}-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)
-4-(6-methylnaphthalen-2-yl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-{4-(2,2-dichlorovinylphenyl}-4-methyl Pentane, 1-(3-phenoxy-4-
Fluorophenyl)-4-(3-fluoro-4-methylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-dichlorofluoromethoxyphenyl)-4-methylpentane , 1-(
3-phenoxy-4-fluorophenyl)-4-(4-
difluoromethoxyphenyl)-5-methylhexane,
1-(3-phenoxy-4-fluorophenyl)-4-
(3-chloro-4-methylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)
-4-(3-bromo-4-fluorophenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(3-fluoro-4-methylphenyl)
-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-5
-Methylhexane, 1-(3-phenoxy-4-fluorophenyl)-4-(3-bromo-4-methylphenyl)-4-methylpentane, 1-(3-phenoxy-4-
Fluorophenyl)-4-(4-isopropylphenyl)-4-methylpentane, 1-(3-phenoxy-4-
Fluorophenyl)-4-(3,4-diisopropylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(3-ethyl-4-methylphenyl)-4-methylpentane , 1-(3-phenoxy-4-fluorophenyl)-4-(4-tert
-butyl-3-methylphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4
-(4-n-propoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-
4-(4-n-propoxyphenyl)-4-methylhexane, 1-(3-phenoxy-4-fluorophenyl)
-4-(4-isopropoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-isopropoxyphenyl)-4-methylhexane, 1-{3-( 4-fluorophenoxy)-4
-Fluorophenyl}-4-(4-ethoxyphenyl)
-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-acetylphenyl)-4
-Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-cyclopentyloxyphenyl)-4-methylpentane, 1-(3-phenoxy-4
-fluorophenyl)-4-(4-n-pentyloxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-isobutoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-iodophenyl)-4-methylpentane, 1-(3-phenoxy-4
-Fluorophenyl)-4-(4-iodophenyl)-
4-Methylhexane, 1-{3-(4-bromophenoxy)-4-fluorophenyl}-4-(4-ethoxyphenyl-4-methylpentane, 1-(3-phenoxy-
4-fluorophenyl)-4-(4-vinyloxyphenyl)-4-methylpentane, 1-(3-phenoxy-4
-fluorophenyl)-4-(4-biphenyl)-4-
Methylpentane, 1(3-phenoxy-4-fluorophenyl)-4-(4-n-butoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-{4-( 2-butoxy)phenyl}-4
-Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-phenoxyphenyl)-4-
Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(3-chloro-4-fluorophenyl)-4-methylpentane, 1-(3-phenoxy-4-
fluorophenyl)-4-(4-cyclohexyloxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-{4-(1,1-difluoro-2-iodoethoxy)phenyl }-4-methylpentane, 1-{3-(4-chlorophenoxy)-4
-Fluorophenyl}-4-(4-ethoxyphenyl)
-4-Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(3-chloro-4-ethoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)- 4-{4-(1,1-difluoroethoxy)phenyl}-4-methylpentane, 1
-(3-phenoxy-4-fluorophenyl)-4-(
4-methoxymethylphenyl)-4-methylpentane,
1-(3-phenoxy-4-fluorophenyl)-4-
(4-ethoxymethoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-
4-(4-propargyloxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxy-3-methoxyphenyl)-
4-Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(3-ethoxyphenyl)-4-
Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-{3,4-bis(difluoroethoxy)phenyl}-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4 -(4-ethylthiophenyl)-4-methylpentane, 1-{3-(4-ethoxyphenoxy)-4-fluorophenyl}-4-(
4-ethoxyphenyl)-4-methylpentane, 1-(
3-phenoxy-4-fluorophenyl)-4-{4-
(2-chlorovinyl)phenyl}-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4
-(4-phenoxy-4-fluorophenyl)-4-(
4-vinylphenyl)-4-methylpentane, 1-(3
-phenoxy-4-fluorophenyl)-4-{4-(
2,2,2-trifluoroethoxycarbonyl)phenyl}-4-methylpentane, 1-(3-phenoxy-4
-fluorophenyl)-4-{4-(2-chloroethoxy)phenyl}-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-{4-(1-methyl-1-propenyl) ) phenyl}-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-
4-{4-(1-ethylvinyl)phenyl}-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-isopropylthiophenyl)-4-
Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-(4-methoxymethylthiophenyl)
-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-4-{4-(2-fluoroethoxy)phenyl}-4-methylpentane, 1-(3-phenoxyphenyl)-1-cyano -4-(4-chlorophenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-1-ethynyl-4-(4-chlorophenyl)-
4-methylpentane, 1-(3-phenoxyphenyl)
-1-cyano-4-(4-ethoxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-1-
Ethynyl-4-(4-ethoxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-1-cyano-4-(4-ethoxyphenyl)-4-methylhexane, 1-(3-phenoxyphenyl) )-1-cyano-4
-(4-difluoromethoxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-1-ethynyl-4-(4-difluoromethoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4 -fluorophenyl)-1-cyano-4-(4-chlorophenyl)-
4-Methylpentane, 1-(3-phenoxy-4-fluorophenyl)-1-ethynyl-4-(4-chlorophenyl)-4-methylpentane, 1-(3-phenoxy-
4-fluorophenyl)-1-cyano-4-(4-ethoxyphenyl)-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-1-ethynyl-4-
(4-ethoxyphenyl)-4-methylpentane, 1-
(3-phenylthio-4-fluorophenyl)-4-(
4-ethoxyphenyl)-4-methylpentane, 1-(
3-phenoxy-4-fluorophenyl)-3-{1-
(4-ethoxyphenyl)cyclobutyl}propane, 1
-(3-phenoxy-4-fluorophenyl)-3-{
1-(4-ethoxyphenyl)cyclopropyl}propane, 1-(3-phenoxy-4-fluorophenyl)-
3-{1-(4-ethoxyphenyl)cyclopentyl}
Propane, 1-(3-phenoxy-4-fluorophenyl)-3-{1-(4-ethoxyphenyl)cyclohexyl}propane, 1-(3-phenoxy-4-fluorophenyl)-3-{1-(4 -chlorophenyl)cyclobutyl}propane, 1-(3-phenoxy-4-fluorophenyl)-3-{1-(4-chlorophenyl)cyclopropyl}propane, 1-(3-phenoxy-4-fluorophenyl)-3- {1-(4-chlorophenyl)
cyclopentyl}propane, 1-(3-phenoxy-4
-fluorophenyl)-3-{1-(4-chlorophenyl)cyclohexyl}propane, 1-{3-(2-pyridyloxy)phenyl}-4-(4-chlorophenyl)
-4-Methylpentane, 1-{3-(2-pyridyloxy)phenyl-4-(4-ethoxyphenyl)-4-methylpentane, 1-{3-(2-pyridyloxy)-4
-Fluorophenyl}-4-(4-ethoxyphenyl)
-4-methylpentane, 1-(3-phenoxy-4-fluorophenyl)-1-cyano-3-{1-(4-ethoxyphenyl)cyclobutyl}propane, 1-{3-(
4-fluorophenoxy)-4-fluorophenyl}-
4-(3-chloro-4-ethoxyphenyl)-4-methylpentane, 1-(3-phenoxyphenyl)-4-{
4-(2-fluoroethoxycarbonyl)phenyl}-
4-methylpentane, 1-(3-phenoxyphenyl)
Examples include -4-{4-1,1,2,2-tetrafluoroethoxycarbonyl)phenyl}-4-methylpentane.

The manufacturing method of the present invention will be described in more detail as follows. That is, general formula (VII) represented by the following chemical formula (45)

[0048]

embedded image (wherein Ar, R1 and R2 have the above meanings)
A ketone represented by the general formula (VIII) R12CHO
(VIII) (in the formula, R12 represents the above-mentioned meaning), or by condensation with the aldehyde of the general formula (X) shown in the following chemical formula 46.

[0049]

embedded image (wherein Ar, R1 and R2 have the above meanings)
Aldehyde represented by and general formula (XI) represented by the following chemical formula 47

[0050]

When condensing a ketone represented by the following formula (wherein R12 represents the above-mentioned meaning), the reaction is carried out without a solvent or in an inert solvent in the presence of a basic or acidic catalyst as a condensing agent. Condensing agents include alkali hydroxide, alkali carbonate, alkali alcoholate, potassium cyanide, alkali acetate, zinc chloride and acetyl chloride, sulfuric acid, hydrohalic acid, aluminum halide, phosphorus oxychloride, triphenylaluminum, alumina, orthophosphorus. Sodium oxide, barium oxide, organic amines and their salts, amino acids, ion exchange resins, etc. can be used, and basic catalysts are preferred. Inert solvents include water, alcohol,
Ether, benzene, acetic acid, etc. can be used.

In some cases, β-oxyketones or β-haloketones may be obtained in the reaction of the above ketone and aldehyde, but these can be easily obtained by dehydration or dehydrohalogenation as shown in the following chemical formula 48 or chemical formula 49. α,β-unsaturated carbonyl compounds of general formula (IX) or (XII) can be obtained.

[0052]

[C48]

[0053]

embedded image (In the formula, Ar, R1, R2 and R12 have the above-mentioned meanings) The α,β-unsaturated carbonyl compound of (IX) or (XII) is reduced and directly represented by the following chemical formula 50. General formula (I)

[0054]

It is also possible to obtain an aromatic alkane derivative represented by the following formula (wherein Ar, R1, R2, and R3 have the meanings described above), but in order to achieve reduction under milder conditions, the following route is used for reduction. do.

The α,β-unsaturated carbonyl compound of (IX) or (XII) is described, for example, in J. H. Brewster
et al, J. Org. Chem
．． , 29, 116 (1964), and the general formula (XVII
I) and (XVI)

[0056]

[C51]

[0057]

By obtaining a mixture of (wherein Ar, R1, R2 and R12 have the above-mentioned meanings) and further reducing them, aromatic alkane derivatives of general formula (I) can be obtained in good yield. You can get it at

The ketone (VII) or (XI) used as a raw material is obtained by reacting the corresponding nitrile with methylmagnesium halide (C.R. Hauser et al.
al, J. Org. Chem. , 15,3
59 (1950)) or by reacting the corresponding carboxylic acid with methyllithium.

The aldehyde (X) used as a raw material reduces the corresponding nitrile (J. Am. Chem.
Soc. , 86, 1085 (1964)) and by reducing the corresponding acid chloride (Org.
．． Reactions, 4, 362 (1948
)). It can also be produced by oxidizing the corresponding alcohol. (Helvetica Chimica A
cta, 54, 868 (1971)).

[0060] Furthermore, the general formula (X
III)

[0061]

embedded image (wherein Ar, R1 and R2 have the above meanings)
Aldehyde represented by and general formula (XIV) or (XV) represented by the following chemical formula 54 or chemical formula 55

[0062]

[C54]

[0063]

When reacting with a compound represented by the formula (wherein R12, R13, R14 and R3 have the meanings given above), the reaction is carried out at -70°C to 100°C in the presence of an inert solvent. Ether, dichloromethane, dimethyl cellosolve, THF, DMF, DMSO, HMPA, benzene, alcohol, etc. can be used as the inert solvent.

The compound of general formula (XIV) or (XV) has R12CHX or R3X (R3 and R12 have the above meanings, and X represents a halogen atom) and (R1
3) 3P or (R14O)3P (R13 and R14
(represents the above meaning) can be easily obtained by reacting.

When a cyano or ethynyl group is introduced into the olefin of general formula (XVI), hydrogen halide is added by a conventional method, and then a cyanide compound or acetylide is reacted.

When introducing a cyano group, it can also be obtained by directly reacting a cyanide with the olefin of general formula (XVI).

When R4 in general formula (I) is a cyano group, the compound represented by general formula (I) is
General formula (XX) represented by the following chemical formula 56

[0068]

embedded image (wherein Ar, R1 and R2 represent the above meanings,
X represents a halogen atom) and a halogenated compound represented by the general formula (XXIII) R12CH2CN (XX
III) (wherein R12 represents the above-mentioned meaning).

In the compound of general formula (I), when the substituent of the Ar group is an alkoxy group, a haloalkoxy group, a haloalkenyloxy group, etc., another easy-to-obtain alkoxy derivative is hydrolyzed to obtain a hydroxy derivative, The desired product can also be obtained by reacting with a corresponding halide.

[0070] Examples of the manufacturing route are shown below.
8, Reaction formulas (1) to (6) shown by chemical formulas 59, 60, 61, and 62 are shown.

[0071]

[C57]

[0072]

[C58]

[0073]

[C59]

[0074]

[C60]

[0075]

[C61]

[0076]

[C62]

Next, the method for producing aromatic alkane derivatives of the present invention will be explained in more detail with reference to synthesis examples.

[0078]

[Synthesis Example 1] 1-(3-phenoxyphenyl)
-Synthesis of -4-(4-methylphenyl)-4-methylpentane

Synthesis was carried out in the following order.

(1) 1-(3-phenoxyphenyl)-4-(4-methylphenyl)-4-methyl-2- and 1-pentene

(a) 2-(4
-methylphenyl)-2-methyl-3-butanone 5.3
g, 3-phenoxybenzaldehyde 6.0g, KOH
6.0 g was added and stirred at room temperature for 1 hour and 20 minutes. Next, the reaction mass was poured into 300 ml of water, and then extracted with benzene. After washing the benzene solution with water and drying, the solvent was distilled off under reduced pressure to obtain crude 1-(3-phenoxyphenyl)-
10.4 g of 4-(4-methylphenyl)-4-methyl-1-penten-3-one was obtained. Next, it was purified by column chromatography (250 g of silica gel, developing solvent benzene) to obtain purified 1-(3-phenoxyphenyl)-
6.8 g of 4-(4-methylphenyl)-4-methyl-1-penten-3-one was obtained.

The physical property values are shown in equation 1 below.

[0083]

[Number 1]

(b) After adding 1.4 g of lithium aluminum hydride to 10 ml of dry ether, a solution of 9.7 g of aluminum chloride in 20 ml of ether was carefully added dropwise. Then, 1-(3-phenoxyphenyl)-4-(4-methylphenyl)-4-methyl-1- obtained in (a)
A solution of 7.4 g of penten-3-one in 10 ml of ether was added dropwise, and the mixture was heated under reflux for 30 minutes. Ethyl acetate and then water were added dropwise to the reaction mass while cooling, followed by extraction with benzene. After washing the benzene solution with water and drying, the solvent was distilled off under reduced pressure. The residue was subjected to column chromatography (silica
150g of gel, developing solvent: benzene-hexane (1:2
)) to give 1-(3-phenoxyphenyl)-4
-(4-methylphenyl)-4-methyl-2-pentene (50%), 1-(3-phenoxyphenyl)-4-(
4-methylphenyl)-4-methyl-1-pentene (5
0%) mixture was obtained.

The physical property values are shown in Equation 2 below.

[0086]

[Number 2]

(2) 1-(3-phenoxyphenyl)-4-(4-methylphenyl)-4-methylpentane

1-(3-phenoxyphenyl)-4-(
4-methylphenyl)-4-methyl-2-pentene (5
0%), 1-(3-phenoxyphenyl)-4-(4-
methylphenyl)-4-methyl-1-pentene (50%
) was dissolved in 30 ml of ethyl acetate.
Add 0.4g of %Pd-C and hydrogen pressure 20k at room temperature.
Stirred at g/cm2G for 3 hours. After the reaction, Pd-C
After filtration, ethyl acetate was distilled off under reduced pressure.

The residue was subjected to column chromatography (50 g of silica gel, developing solvent: benzene-hexane (1
:2)) to obtain 1.8 g of the desired 1-(3-phenoxyphenyl)-4-(4-methylphenyl)-4-methylpentane.

The physical property values are shown in equation 3 below.

[0091]

[Math 3]

[0092]

[Synthesis Example 2] 1-(3-phenoxyphenyl)
Synthesis of -4-(3-trifluoromethylphenyl)-4-methylpentane

Synthesis was carried out in the following order.

(1) 1-(3-phenoxyphenyl)-4-(3-trifluoromethylphenyl)-4-methyl-2- and 1-pentene

(a) 4.3 g of 2-(3-trifluoromethylphenyl)-2-methyl-3-butanone and 3.7 g of 3-phenoxybenzaldehyde in 30 ml of ethanol.
, KOH (1.0 g) was added thereto, and the mixture was stirred at room temperature all day and night. After discharging the reaction mass into 300 ml of water, it was extracted with benzene, and the extract was washed with water, dried, and the solvent was distilled off under reduced pressure to obtain 7.5 g of a residue. The residue was subjected to column chromatography (
Purified with 210 g of silica gel, developing solvent: benzene) and purified 1-(3-phenoxyphenyl)-4-(3-trifluoromethylphenyl)-4-methyl-1-penten-3-one. 5.9g of was obtained.

The physical property values are shown in Equation 4 below.

[0097]

[Math 4]

(b) 0.71 g of lithium aluminum hydride was added to 10 ml of dry ether, and a solution of 5.0 g of anhydrous aluminum chloride/20 ml of dry ether was added dropwise thereto. After completion of the dropping, 4.4 g of 1-(3-phenoxyphenyl)-4-(3-trifluoromethylphenyl)-4-methyl-1-penten-3-one obtained in (a)
A 20 ml solution of dry ether was added dropwise and the mixture was heated to reflux for 30 minutes. While cooling with ice water, ethyl acetate and water were added dropwise to the reaction mass in this order to complete the reaction. Then,
After extraction with benzene, the extract was washed with water, dried, and the solvent was distilled off under reduced pressure to obtain 4.4 g of a residue.

The residue was subjected to column chromatography (100 g of silica gel, developing solvent: benzene-hexane (1
:2)) to produce 1-(3-phenoxyphenyl)
-4-(3-trifluoromethylphenyl)-4-methyl-2-pentene (70%), 1-(3-phenoxyphenyl)-4-(3-trifluoromethylphenyl)-
A mixture of 4-methyl-1-pentene (30%) was added to 2.2
I got g.

The physical property values are shown in Equation 5 below.

[0101]

[Math 5]

(2) 1-(3-phenoxyphenyl)-4-(3-trifluoromethylphenyl)-4-methylpentane

1-(3-Phenoxyphenyl)-4-(3-trifluoromethylphenyl)-4-methyl-2-pentene (70%), 1-(3-
Add 1.2 g of a mixture of (phenoxyphenyl)-4-(3-trifluoromethylphenyl)-4-methyl-1-pentene (30%) and 0.40 g of 5% Pd-C, and add 20 kg/h of hydrogen. The mixture was pressurized to cm2G and stirred at 65°C for 3 hours. After the reaction, Pd-C was filtered off, and the solvent was distilled off under reduced pressure.
A residue of 1.2 g was obtained. The residue was purified by column chromatography (25 g of silica gel, developing solvent: benzene-hexane (1:2)) to obtain 1-(3-phenoxyphenyl)-4-(3-trifluoromethyl phenyl)-4
-0.8 g of methylpentane was obtained.

The physical property values are shown in Equation 6 below.

[0105]

[Math 6]

[0106]

[Synthesis Example 3] 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4-
Synthesis of methylpentane

Synthesis was carried out according to the following order.

(1) 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4
-methyl-2- and 1-pentene

(a) 2-(4-ethoxyphenyl)
Using 6.2 g of -2-methyl-3-butanone and 6.5 g of 3-phenoxy-4-fluorobenzaldehyde,
After processing in the same manner as in (1)-(a) of Synthesis Example 2, the remaining 12
．． Obtained 0g. Column chromatography (silica
Purify with 200g of gel, developing solvent: benzene) and obtain 1-(
3-phenoxy-4-fluorophenyl)-4-(4-
ethoxyphenyl)-4-methyl-1-pentene-3-
5.8 g of on was obtained.

The physical property values are shown in Equation 7 below.

[0111]

[Math 7]

(b) 1-(3-Phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4-methyl-1-penten-3-one 4.1 obtained in (a)
Using g, the same treatment as in (1) to (b) of Synthesis Example 2 was carried out to obtain 3.9 g of a residue. The residue was purified by column chromatography (80 g of silica gel, developing solvent: benzene-hexane (2:3)) to obtain 1-(3-phenoxy-
4-fluorophenyl)-4-(4-ethoxyphenyl)-4-methyl-2-pentene (45%), 1-(3-
Phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4-methyl-1-pentene (55%)
1.44g of a mixture was obtained.

The physical property values are shown in Equation 8 below.

[0114]

[Math. 8]

(2) 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4
methylpentane

1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4-methyl 2
-Pentene (45%), 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4
0.9 g of a mixture of -methyl-1-pentene (55%) was reduced and treated according to Synthesis Example 2 (2). Residue 1
．． Column chromatography (20 g of silica gel, developing solvent: benzene-hexane (2:3))
Purification was performed to obtain 0.80 g of 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4-methylpentane.

The physical property values are shown in Equation 9 below.

[0118]

[Math. 9]

[0119]

[Synthesis Example 4] 1-(3-phenoxyphenyl)
Synthesis of -4-(3,4-methylenedioxyphenyl)-4-methylpentane

Synthesis was carried out in the following order.

(1) 1-(3-phenoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-
Methyl-1- and 2-pentene

(a) 2-(3,4-methylenedioxyphenyl)-2-methyl-3-butanone 10 g, 3-
Phenoxybenzaldehyde 9.6g, ethanol 50
ml and 2 g of KOH was stirred at 60° C. for 30 minutes. Next, the reaction mass was poured into 300 ml of water and extracted with benzene. The benzene layer was washed with water, dried, and the solvent was distilled off under reduced pressure to obtain 23 g of a residue. The residue was separated by column chromatography (silica gel, developing solvent: benzene),
15.3 g of purified 1-(3-phenoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-methyl-1-penten-3-one was obtained.

The physical property values are shown in Equation 10 below.

[0124]

[Math. 10]

(b) 12 g of 1-(3-phenoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-methyl-1-penten-3-one obtained in (a) was added. Treated according to Synthesis Example 1-(b) to obtain 1-(3-phenoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-methyl-2-pentene (40%) ,1-
(3-phenoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-methyl-1-pentene (60
%) mixture was obtained.

The physical property values are shown in Equation 11 below.

[0127]

[Math. 11]

(2) 1-(3-phenoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-
methylpentane

Mixture of 1-(3-phenoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-methyl-1- and 2-pentene obtained in (1)-(b) was treated according to Synthesis Example 1-(2), and quantitatively 1-(
3-phenoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-methylpentane was obtained.

The physical property values are shown in Equation 12 below.

[0131]

[Math. 12]

[0132]

[Synthesis Example 5] 1-(3-phenoxyphenyl)
Synthesis of -4-(4-methoxyphenyl)-4-methylpentane

Synthesis was carried out according to the following order.

(1) 1-(3-phenoxyphenyl)-4-(4-methoxyphenyl)-4-methyl-1-
and 2-pentene

(a) 2-(4-methoxyphenyl)
-2-methyl-3-butanone 10g, 3-phenoxybenzaldehyde 33.7g, methanol 80ml, KO
A mixture of 4.0 g of H was stirred at 40° C. for 2 hours to react. The following treatment was carried out according to Synthesis Example 1-(1)-(a), and 1
25 g of -(3-phenoxyphenyl)-4-(methoxyphenyl)-4-methyl-1-penten-3-one was obtained.

The physical property values are shown in Equation 13 below.

[0137]

[Math. 13]

(b) 1-(3-phenoxyphenyl)-4-(4-methoxyphenyl)-4- obtained in (a)
25.7 g of methyl-1-penten-3-one was treated according to Synthesis Example 1-(1)-(b) to obtain 1-(3-phenoxyphenyl)-4-(4-methoxyphenyl). )-4
-Methyl-2-pentene (40%), 1-(3-phenoxyphenyl)-4-(4-methoxyphenyl)-4-
9.0 g of a mixture of methyl-1-pentene (60%) was obtained.

The physical property values are shown in Equation 14 below.

[0140]

[Math. 14]

(2) 1-(3-phenoxyphenyl)-4-(4-methoxyphenyl)-4-methylpentane

1-(3-phenoxyphenyl)-4-(4-methoxyphenyl)-4-methyl- obtained in (1)
Synthesis of a mixture of 2 and 1-pentenes Example 1-(2)
1-(3-phenoxyphenyl)-4-(4-methoxyphenyl)-4-methylpentane was quantitatively obtained.

The physical property values are shown in Equation 15 below.

[0144]

[Math. 15]

[0145]

[Synthesis Example 6] 1-(3-phenoxy-4-fluorophenyl)-4-(4-methoxyphenyl)-4-
Synthesis of methylpentane

(1) 2-(4-methoxyphenyl)
A mixture of 7.6 g of -2-methyl-3-butanone, 8.5 g of 3-phenoxy-4-fluorobenzaldehyde, 30 ml of methanol, and 2 g of KOH was stirred at 60° C. for 2 hours to react. Synthesis of reaction mass Example 1-(1)(a
) to obtain 5 g of 1-(3-phenoxy-4-fluorophenyl)-4-(4-methoxyphenyl)-4-methyl-1-penten-3-one.

The physical property values are shown in Equation 16 below.

[0148]

[Math. 16]

1-(3-phenoxy-4-fluorophenyl)-4-(4-methoxyphenyl)-4 obtained above
-Methyl-1-penten-3-one (4.2 g) was treated according to Synthesis Example 1-(1)-(b), and 1-(3-phenoxy-4-fluorophenyl)-4-(4 -methoxyphenyl)-4-methyl-2-pentene (50%), 1
-(3-phenoxy-4-fluorophenyl)-4-(
4-methoxyphenyl)-4-methyl-1-pentene (
50%) mixture was obtained.

The physical property values are shown in Equation 17 below.

[0151]

[Math. 17]

(2) Synthesis Example 1 of the mixture of 1-(3-phenoxy-4-fluorophenyl)-4-(4-methoxyphenyl)-4-methylpentene obtained in (1)
- Treated according to (2), 1-(3-phenoxy-4-
Fluorophenyl)-4-(4-methoxyphenyl)-
4-Methylpentane was obtained quantitatively.

The physical property values are shown in Equation 18 below.

[0154]

[Math. 18]

[0155]

[Synthesis Example 7] 1-(3-phenoxyphenyl)
-Synthesis of 4-(4-chlorophenyl)-4-methylhexane

According to Synthesis Example 2, 3-(4-chlorophenyl)-3-methyl-2-pentanone and 3-phenoxybenzaldehyde were reacted to form 1-(3-phenoxyphenyl)- 4-(4-chlorophenyl)-4
-Methyl-hexane was obtained.

The physical property values are shown in Equation 19 below.

[0158]

[Math. 19]

[0159]

[Synthesis Example 8] 1-(3-phenoxyphenyl)
Synthesis of -4-(4-chlorophenyl)-4-methylpentane

An equivalent mixture of α,α-dimethyl-(4-chlorophenyl)acetaldehyde and 3-phenoxyacetophenone was reacted according to Synthesis Example 2 to obtain 1-
(3-phenoxyphenyl)-4-(4-chlorophenyl)-4-methylpentane was obtained.

[0161] Its physical property values are shown in Equation 20 below.

[0162]

[Math. 20]

[0163]

[Synthesis Example 9] 1-(3-phenoxyphenyl)
Synthesis of -4-(4-isopropoxyphenyl)-4-methylpentane

(1) 1-(3-phenoxyphenyl)-4-(4-methoxyphenyl)-4-methylpentane 5.0 g, 47% aq HBr 30 ml,
A mixture of 30 ml of acetic acid was heated under reflux for 8 hours. The reaction mass was poured into water and extracted with benzene. The benzene layer was washed with water, dried, the solvent was distilled off under reduced pressure, and the residue was transferred to a column.
Purified by chromatography (silica gel, developing solvent: benzene) to obtain 1-(3-phenoxyphenyl)-4-
(4-hydroxyphenyl)-4-methylpentane 4
．． I got 2g.

The physical property values are shown in Equation 21 below.

[0166]

[Math. 21]

(2) 1-(3-phenoxyphenyl)-4-(4-hydroxyphenyl)-4 obtained in (1)
- A mixture of 0.5 g of methylpentane, 1.5 g of K2CO3, 3 ml of isopropyl bromide, and 20 ml of dimethylformamide was reacted at 130 DEG C. with stirring for 2 hours. The reaction mass was poured into water and extracted with benzene. The benzene layer was washed with water, dried, the solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography (silica gel, developing solvent;
1-(3-phenoxyphenyl)
0.3 g of -4-(4-isopropoxyphenyl)-4-methylpentane was obtained.

The physical property values are shown in Equation 22 below.

[0169]

[Math. 22]

[0170]

[Synthesis Example 10] Synthesis of 1-(3-phenoxy-4-fluorophenyl)-4-(4-difluoromethoxyphenyl)-4-methylpentane

(1) 1-(3-phenoxy-4-fluorophenyl)-4-(4-methoxyphenyl)-4
- 1 g of methylpentane is treated according to Synthesis Example 9,
1-(3-phenoxy-4-fluorophenyl)-4-
(4-hydroxyphenyl)-4-methylpentane 0.
6g was obtained.

The physical property values are shown in Equation 23 below.

[0173]

[Math. 23]

(2) 0.5 g of 1-(3-phenoxy-4-fluorophenyl)-4-(4-hydroxyphenyl)-4-methylpentane obtained in (1), 1.0 g of KOH.
Chlorodifluoromethane was passed through a mixture of 0 g and 20 ml of acetonitrile at 60° C. for 30 minutes with stirring. The reaction mass was poured into water and extracted with benzene. The benzene layer was washed with water, dried, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel, developing solvent: benzene) to obtain 1-(3-phenoxy-4-fluoro). 0.4 g of phenyl)-4-(4-difluoromethoxyphenyl)-4-methylpentane was obtained.

The physical property values are shown in Equation 24 below.

[0176]

[Math. 24]

[0177]

[Synthesis Example 11] 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4
-Synthesis of methylpentane

Synthesis was carried out according to the following order.

(1) 7 ml of triethyl phosphorite was added to 6.4 g of 3-phenoxy-4-fluorobenzyl bromide, and the mixture was reacted with stirring at 140° C. for 7 hours. After cooling, 13.1 g of the reaction mass was subjected to column chromatography (silica gel, developing solvent: benzene), and diethyl 3-phenoxy-4-fluorobenzylphosphonate 6
．． 3g was obtained.

The physical property values are shown in equation 25 below.

[0181]

[Math. 25]

(2) 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4
-methyl-1-pentene

[0183] Sodium hydride (60%) 0.36g/
In a solution of 10 ml of dry dimethyl cellosolve, add 3.0 ml of diethyl 3-phenoxy-4-fluorobenzylphosphonate.
g/dry dimethyl cellosolve 10ml solution was added dropwise, 5
The mixture was stirred at 0°C for 30 minutes. Then add 1.3-(4-ethoxyphenyl)-3-methyl-butyraldehyde to the mixture.
55g/5ml dry dimethyl cellosolve solution was added dropwise,
The reaction was carried out at 50° C. for 1 hour while stirring. The reaction mass was poured into water and extracted with benzene. The organic layer was washed with water, dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was separated using column chromatography (silica gel).
-(3-phenoxy-4-fluorophenyl)-4-(
4-ethoxyphenyl)-4-methyl-1-pentene 2
．． 49g was obtained.

The physical property values are shown in Equation 26 below.

[0185]

[Math. 26]

(3) 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4
-Methylpentane

2.0 g of 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4-methyl-1-pentene in a 200 ml autoclave, P
0.2 g of d-C (5%) and 40 ml of ethyl acetate were charged, the pressure was increased to 10 kg/cm2G with hydrogen, and the mixture was stirred and reacted at 80° C. for 3 hours. After cooling, the reaction mass was filtered, the solvent was distilled off from the filtrate, and the residue was purified by column chromatography (silica gel) to 1-(3-phenoxy-4
-fluorophenyl)-4-(4-ethoxyphenyl)
1.7 g of -4-methylpentane was separated.

The physical property values are shown in Equation 27 below.

[0189]

[Math. 27]

The IR spectrum and NMR spectrum were consistent with those obtained in Synthesis Example 3.

[0191]

[Synthesis Example 12] Triphenylphosphine and a slight excess of 3-phenoxy-4-fluorobenzyl bromide are mixed in benzene at -10°C in a tight flask and left at room temperature overnight to precipitate crystals. The crystals were separated by filtration, washed with benzene, and then dried. Phenyl lithium 40 mmol/
40 mmol of the crystalline bromide obtained above was added to a 150 ml solution of dry ether in a nitrogen stream, and the mixture was reacted with stirring for 3 hours. The generated lithium bromide was filtered off to obtain a solution. In dry ether, equimolar amount of 3-(
After adding 4-ethoxyphenyl)-3-methyl-butyraldehyde while cold, the temperature was raised, and after distilling off the ether, the mixture was reacted at 65°C for 3 hours, then poured into water, and extracted with benzene. , the benzene layer was washed with water, the solvent was distilled off after drying,
The residue was separated and purified by column chromatography (silica gel) to obtain 1-(3-phenoxy-4-fluorophenyl)-4-(4-ethoxyphenyl)-4-methyl-
1-pentene was obtained.

The physical property values are shown in Equation 28 below.

[0193]

[Math. 28]

The IR spectrum and NMR spectrum matched those obtained in Synthesis Example 11-(2).

[0195]

[Synthesis Example 13] 1-(3-benzoylphenyl)-4-(3-bromo-4-ethoxyphenyl)-4-
Synthesis of methylpentane

Synthesis was carried out in the following order.

(1) 1-(3-benzoylphenyl)-4-(3-bromo-4-ethoxyphenyl)-4-
Methyl-1-pentene

0.1 g of 60% sodium hydride was added to 5 ml of anhydrous dimethyl cellosolve, and then 3-benzoylbenzylphosphonic acid diethyl ester (Synthesis Example 1) was added to 5 ml of anhydrous dimethyl cellosolve.
1-(1)) After dropping 0.9 g of
The mixture was stirred at ℃ for 30 minutes. Next, add 3-
A solution of 0.6 g (3-bromo-4-ethoxyphenyl)-3-methylbutanal in 2 ml dimethyl cellosolve was added dropwise. Further, the mixture was reacted at 80° C. for 1 hour with stirring. After cooling, the reaction mass was poured into water, extracted with benzene, and the benzene layer was washed with water, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: benzene) to obtain 0.7 g of the desired product.

The physical property values are shown in Equation 29 below.

[0200]

[Math. 29]

(2) 1-(3-benzoylphenyl)-4-(3-bromo-4-ethoxyphenyl)-4-
methylpentane

1-(3-benzoylphenyl)-4-(3-bromo-4-ethoxyphenyl)-4 obtained in (1)
-Methylpentene was treated according to Synthesis Example 2-(2) to obtain 1-(3-benzoylphenyl)-4-(3-bromo-4-ethoxyphenyl)-4-methylpentane.

The physical property values are shown in Equation 30 below.

[0204]

[Math. 30]

[0205]

[Synthesis Example 14] 1-(3-benzylphenyl)
Synthesis of -4-(4-ethoxyphenyl)-4-methylpentane

Synthesis was carried out in the following order.

(1) 1-(3-benzylphenyl)
-4-(4-ethoxyphenyl)-4-methyl-1-pentene

0.1 g of lithium aluminum hydride was added to 5 ml of dry ether, and then 0.1 g of lithium aluminum hydride was added to 5 ml of dry ether.
．． A solution of 7 g/10 ml dry ether was added. To this suspension, 0.54 g of 1-(3-benzoylphenyl)-4-(4-ethoxyphenyl)-4-methyl-1-pentene (prepared according to Synthesis Example 12-(1)) was added. 2 ml of dry ether solution was added dropwise, and the mixture was heated under reflux for 30 minutes. After cooling to room temperature, ethyl acetate was added dropwise to decompose excess reducing agent, and the mixture was poured into ice water and extracted with benzene. The benzene solution was washed with water, dried, concentrated under reduced pressure, and purified by silica gel column chromatography (developing solvent: benzene-hexane (1:2)) to obtain the desired product (0.4%).
5g was obtained.

The physical property values are shown in Equation 31 below.

[0210]

[Math. 31]

(2) 1-(3-benzylphenyl)
-4-(4-ethoxyphenyl)-4-methylpentane

1-(3-Benzylphenyl)-4-(4-ethoxyphenyl)-4-methyl-1- obtained in (1)
Pentene was reduced according to Synthesis Example 2-(2) to obtain 1-(3-benzylphenyl)-4-(4-ethoxyphenyl)-4-methylpentane.

[0213] Its physical property values are shown in Equation 32 below.

[0214]

[Math. 32]

Next, a typical synthesis example of 2-aryl-2-methyl-3-butanones as a starting material is shown below.

[0216]

[Synthesis Example 15] 2-(4-methylphenyl)-
Method for producing 2-methyl-3-butanone

After adding 9.0 g of metallic magnesium (shavings) and 100 mg of I2 as a catalyst to 50 ml of dry ether, 25 ml of iodomethane was gradually added dropwise. After the addition was complete, the reaction mass was refluxed for 30 minutes. Next, 200 ml of dry benzene was added to the reaction mass, heated until the internal temperature reached 80° C., and after distilling off the ether, a solution of 45.6 g of α,α-dimethyl-4-methylbenzylnitrile in 50 ml of benzene was added dropwise. After refluxing for 3 hours, 150 ml of 6N-HCl was carefully added dropwise to the reaction mass while cooling it with ice water. After refluxing for one hour, the mixture was cooled to room temperature and the benzene layer was separated. After washing the benzene solution with water, it was dried over anhydrous sodium sulfate, and the benzene was distilled off under reduced pressure, leaving a residue of 45.2
I got g. Next, distillation was carried out under reduced pressure to obtain 20.0 g (94
~95°C/5mmHg).

The physical property values are shown in equation 33 below.

[0219]

[Math. 33]

[0220]

[Synthesis Example 16] 2-(4-chlorophenyl)-
Method for producing 2-methyl-3-butanone

After adding 13.0 g of metallic magnesium (shavings) and a catalytic amount of I2 to 100 ml of dry ether, 66 g of iodomethane was carefully added dropwise. After the addition was complete, the reaction mass was refluxed for 1 hour. Next, 150 ml of dry benzene was added to the reaction mass and heated until the internal temperature reached 80°C to distill off the ether, replacing the ether with benzene.

[0222] Add α,α-dimethyl-4- to the benzene solution.
A solution of 45 g of chlorobenzyl nitrile/30 ml of benzene was added dropwise, and the mixture was refluxed for 3 hours. While cooling the reaction mass with ice water, 270 ml of 6N-HCl was carefully added dropwise. After the dropwise addition was completed, the mixture was refluxed for 8 hours, cooled to room temperature, and the benzene layer was separated. After washing the benzene solution with water and drying, the solvent was distilled off under reduced pressure to obtain 52 g of a residue. This residue was distilled under reduced pressure, and the purified 2
43.0 g (104° C./5 mmHg) of -(4-chlorophenyl)-2-methyl-3-butanone was obtained.

The physical property values are shown in Equation 34 below.

[0224]

[Math. 34]

[0225]

[Synthesis Example 17] 2-(4-methoxyphenyl)
-Production method of 2-methyl-3-butanone

[0226] In the same manner as in Synthesis Example 15, using 58 g of α,α-dimethyl-4-methoxybenzylnitrile, 51.4 g (106 ~111°C/4mmHg) was obtained.

[0227] Its physical property values are shown in Equation 35 below.

[0228]

[Math. 35]

[0229]

[Synthesis Example 18] Method for producing 2-(3,4-methylenedioxyphenyl)-2-methyl-3-butanone

0
230 In the same manner as in Synthesis Example 15, 93 g of α,α-dimethyl-3,4-methylenedioxybenzylnitrile
83.2 g (116-1
17°C/0.9mmHg).

[0231] Its physical property values are shown in Equation 36 below.

[0232]

[Math. 36]

[0233]

[Synthesis Example 19] 2-(4-ethoxyphenyl)
-Production method of 2-methyl-3-butanone

[0234] In the same manner as in Synthesis Example 15, the purified 2-(4
-ethoxyphenyl)-2-methyl-3-butanone 44
．． 0g (115°C/4mmHg) was obtained.

The physical property values are shown in Equation 37 below.

[0236]

[Math. 37]

[0237]

[Synthesis Example 20] Method for producing 2-(3-trifluoromethylphenyl)-2-methyl-3-butanone

02
38] 10 g of α,α-dimethyl-3-trifluoromethylbenzyl nitrile was treated in the same manner as in Synthesis Example 16 to obtain 9.6 g of a residue. The residue was purified by column chromatography (200 g of silica gel, developing solvent: benzene) to obtain purified 2-(3-trifluoromethylphenyl)-2.
-Methyl-3-butanone (4.3 g) was obtained.

The physical property values are shown in Equation 38 below.

[0240]

[Math. 38]

Representative compounds of the present invention are shown in Table 1 shown in Tables 1 to 26 below.

[0242]

[Table 1]

[0243]

[Table 2]

[0244]

[Table 3]

[0245]

[Table 4]

[0246]

[Table 5]

[0247]

[Table 6]

[0248]

[Table 7]

[0249]

[Table 8]

0250]

[Table 9]

[0251]

[Table 10]

0252]

[Table 11]

0253]

[Table 12]

0254]

[Table 13]

0255]

[Table 14]

0256]

[Table 15]

0257]

[Table 16]

[0258]

[Table 17]

0259]

[Table 18]

0260]

[Table 19]

[0261]

[Table 20]

0262]

[Table 21]

0263

[Table 22]

0264

[Table 23]

The compounds of the present invention are effective against sanitary pests such as flies, mosquitoes,
In addition to cockroaches, planthoppers, leafhoppers, armyworms,
It is highly effective against agricultural pests such as diamondback moths, leaf mites, aphids, caterpillars, and spider mites, especially against leafhoppers, and is also extremely effective against grain storage pests such as mealybugs, yellowtail moths, and black elephants, as well as animal-parasitic lice and mites. and is also effective against other pests. Furthermore, the compound of the present invention has excellent fast-acting properties and residual effectiveness, and also has a flushing effect. The compound of the present invention not only knocks down and kills pests, but also has repellent properties and has the effect of repelling pests from the host. It has the great advantage of not causing any phytotoxicity to nightshade plants. In addition, it has low toxicity to mammals. Some of the compounds of the present invention are also highly safe for fish, and are not only suitable for exterminating pests in rice fields, but also for exterminating aquatic pests such as mosquitoes and black fly larvae. Or a lake, a swamp,
Even when using aircraft to exterminate pests in large areas dotted with ponds and rivers, it can be used without the risk of killing fish living there.

[0266] Therefore, insecticides containing the compounds of the present invention,
Acaricides are used in an extremely wide range of situations, including agricultural and horticultural pests,
It is highly active as an insecticide and acaricide for grain storage pests, sanitary pests, house pests, forest pests, and many other aquatic pests, and is extremely safe and can be put to practical use in various formulations at low cost.

[0267] Next, the names of specific pests to which the insecticide and acaricide of the present invention can be applied are listed [scientific name - (Japanese name) - English name].

[0268] [1. Hemiptera

[
0269 Nephotettix cinctic
eps Uhler (black leafhopper) Gre
en rice leafhopper

0270
】Sogata furcifera Horva
th (White-backed Planthopper) White-backed
rice plant hopper

0271
】Nilaparvata lugens Sto
l (Brown rice)
planthopper

0272 Laodelphax striate
llus Fallen Sm
all brown planthoppers

0
273]Eurydema rugosum Mo
tschulsky (nagame) Cabbage
bug

0274 Eysarcoris parvus
Uhler Whitesp
otted spined bug

0275 Haryomorpha mista
Uhler Brown-ma
rmorated stink bug

[0276] Lagynotomus elonga
tus Dallas Rice
stink bug

0277 Nezara viridula L
inne (Southern stink bug) Southern
green stink bug

Cletus trigonus T
hunberg Slender
rice bug

Stephanitis nashi
Esaki et Takeya Japanese pear lace
bug

Stephanitis pyr
ioides Scott A
zalea lace bug

0281 Psylla pyrlsuga F
oerster Pear su
cker

0282 Psylla mali S
chmidberger App
le soccer

[0283] Aleurolobus taonab
ae Kuwana (grape whitefly) Gra
pe whitefly

0284 Dialeurodes citri
Ashmead Citrus
whitefly

0285 Thialeurodes vapor
ariorum Westwood Greenhouse whitefly

0286 Aphis gossypii Gl
over (cotton aphid) Cotton aphi
d

0287 Brevicoryne brass
icae Linne (radish aphid) C
abbage aphid

Myzus persicae Su
lzer (green peach aphid) Green p.
each aphid

0289 Rhopalosiphum maid
is Fitch Co
rn leaf aphid

0290 Icerya purchasi M
askell Cotton
cushion scale

0291 Planococcus citri
Risso (citrus mealybug) Citr
us mealybug

[0292] Unaspis yanonensis
Kuwana Arro
whead scale

[0293] [2. Lepidoptera (Lepidoptera)
]

Canephora asiatica
Staudinger (Minoga) Mulberry
bagworm

0295 Spulerina astaurct
a Meyrick (Nashihosoga) Pear bar
rk miner

Phyllonorycter rin
goneella Matsumura Apple leafminer

029
7] Plutella xylostella L
inne (konaga) Diamond back m
oth

[0298] Promalactis inopis
ema Butler Cotton
seedworm

0299 Adoxophyes orana
Fischer von Roeslerstam
m (Kokakumonhamaki) Smaller tea
tortrix

0300 Bactra furfurana
Haworth Mat rus
h worm

0301 Leguminivora glyci
nivorella Matsumura Soybean pod borer

0302] Cnaphalocrosis med
inalis Guenee R
ice leaf roller

0303 Etiella zinckenell
a Treitschke (Lima-bean pod borer)

0304 Ostrinia furnacali
s Guenee Oriental
corn borer

0305 Pleuroptya derogat
a Fabricius Cot
ton leaf roller

0306 Hyphantria cunea
Drury (American white flycatcher) Fall w
ebworm

0307 Abraxas miranda B
utler Magpie
moth

0308 Lymantria dispar
japonica Motschulsky Gypsy moth

0309 Phalera fiavescens
Bremer et Gray (Monkuroshishachihoko) Cherry caterpill
ar

0310 Agrotis segetum
Denis et Schiffer
ller (Kaburayaga) Cutworm

0311 Helicoverpa armige
ra Huebner Cott
on ball worm

0312 Pseudaletia separa
ta Walker Armyworm

0313 Mamestra brassicae
Linne Cabbage arm
yworm

0314 Plusia nigrisigna
Walker (Tamanaginuwaba) Beet se
mi-looper

0315 Spodoptera litura
Fablicius Comm
on cutworm

0316 Parnara guttata B
remer et Gray (rice beetle)
Rice skipper

0317 Pieris rapae cruc
ivora Boisduval
Common cabbageworm

Chilo suppressalis
Walker (Nikameiga) Rice st
em borer

0319] [3. Coleoptera

0320 Melanotus fortnumi
Candeze (Marukubikushikometsuki) Sw
eetpotato wireworm

0321 Anthrenus verbasci
Linne (Himemarukatsuobushimushi) Var
ied carpet beetle

0322 Tenebroides maurit
anicus Linne (Kokunust) Cad
elle

0323 Lyctus brunneus S
tephens Powder
post beetle

0324 Henosepilachna vig
intioctopunctata Fabricius
(Nijyuyahoshitento) 28-spotted
lady beetle

0325 Monochamus alterna
tus Hope (Matsunomadara longhorn beetle) Ja
panese pine sawyer

[0326] Xylotrechus pyrrho
derus Bates
Grape borer

0327 Aulacophora femora
lis Motschulsky
Cucurbit leaf beetle

03
28] Oulema oryzae Kuwaya
ma (rice leaf beetle) Rice leaf
beetle

0329 Phyllotreta striol
ata Fablicius
Striped flea beetle

03
30] Callosobruchus chinen
sis Linne (Azuki beetle) Azuk
i bean weevil

0331 Echinocnemis squam
eus Billberg (rice weevil) Ri
ce plant weevil

[0332] Sitophilus oryzae
Linne Riceweeville

0
333] Apoderus erythrogast
er Vollenhoven Small black leaf-cut
weevil

0334 Rhynchites heroes
Roelofs Pea
ch curculio

0335 Anomala cuprea Ho
pe Cupreous c
hafer

0336 Popillia-japonica
Newman Japanese
beetle

[0337] [4. Hymenoptera (Hymenoptera)
]

0338] Athalia rosae jap
onensis Rohwer
Cabbage sawfly

0339 Arge similis Vol.
enhoven (Rurichu Range)Azalea
argid sawfly

0340] Arge pagata Panze
r (Churunjibee) Rose argid
sawfly

0341] [5. Diptera

03
42】Tipula aino Alexander
r (Kiriuji Ganbo) Rice crane
fly

0343 Culex pipiens fat
igans Wiedemann (Aedes aegypti)
House Mosquito

0344 Aedes aegypti Lin
ne (Aedes aegypti) Yellow-fever
mosquito

[0345] Asphondylia sp. (Soybean pod fly) Soybeanpod gal
l midge

0346 Hylemya antiqua M
eigen Onion maggo
t

0347 Hylemya platura
Meigen Seed corn
maggot

0348 Musca domestica v
icina Macquart (Housefly) Ho
use fly

0349 Dacus cucurbitae
Coquillett Melon f
ly

0350 Chlorops oryzae
Matsumura Rice
stem maggot

0351 Agromyza oryzae M
unakata (rice leafminer) Rice le
afminer

0352] [6. Siphonaptera

0353 Pulex irritans Li
nne (human flea) Human flea

03
54]Xenopsylla cheopis R
othschild Tro
pical rat flea

[0355]Ctenocephalides ca
nis Curtis Dog flea
a

0356] [7. Thysanoptera

0357: Scirtothrips dorsa
lis Hood Y
yellow tea strips

0358]Thrips tabaci Lin
deman Onion th
rips

0359 Chloethrips or
yzae Williams (rice thrips)
Rice strips

[0360] [8. Anoplura

[
0361 Pediculus humanus
corporis De Geer Body louse

0362 Phthirus pubis Li
nne (Pubbed Lice) Crab louse

03
63] Haematopinus euryster
nus Nitzsh (cow lice) Short
-nosed cattle louce

036
4] [9. Psocoptera

0365 Trogium pulsatsriu
m Linne (cochatate) Larger
pale booklouse

0366 Liposcelis bostryc
Hophilus Badonnel Flattened booklice

0
367] [10. Orthoptera

0368 Gryllotalpa africa
Beauvois
(kera) African mole cric
ket

0369 Locusta migrato
ria danica Linne Asiatic locust

0370 Oxya yezoensis Sh
iraki Short-winged
rice grass hopper

037
1] [11. Dictyoptera

0372 Blattella germanic
a Linne (German cockroach) German
cockroach

0373 Periplaneta fuligi
nosa serville (black cockroach) S
moky-brown cockroach

037
4] [12. Acarina (Acarina)

0375]
Boophilus microplus Can
estrini Bull ti
ck

0376 Polyphagotarsonemus
latus Banks (Chano dust mite)
Broad mite

0377 Panonychus citri
McGregor Citrus
red mite

0378 Tetranychus cinnab
arinus Boisduval Carmine spider mite

[
0379 Tetranychus urticae
Koch (two-spot)
ted spider mite

0380 Rhizoglyphus echin
ophus Fumouze et Robin (Nedani) Bulb mite

[0381] When actually applying the compound of the present invention,
Although it can be used alone without the addition of other ingredients, in order to make it easier to use as a pest control agent, it is formulated with a carrier.
This is generally applied by diluting it as necessary. The compounds of the present invention can be formulated into emulsions, wettable powders, powders, granules, fine granules, oils, aerosols, It can be prepared into any dosage form such as heating fumigants (mosquito coils, electric mosquito repellents, etc.), fogging agents such as focking, non-heating fumigants, poison baits, etc., and these can be used for various purposes depending on the purpose. .

[0382] Furthermore, by using two or more of these compounds of the present invention in combination, it is possible to express superior insecticidal and acaricidal activity, and other physiologically active substances such as allethrin, N-(chrysansemoylmethyl )-3,4,5
, 6-tetrahydrophthalimide, 5-benzyl-3-
Furylmethyl chrysanthemate, 3-phenoxybenzyl chrysanthemate, 5-propargyl furfuryl chrysanthemate, other known cyclopropane carboxylic acid esters, 3-phenoxybenzyl 2,2-dimethyl-
3-(2,2-dichlorovinyl)-cyclopropane-1
-carboxylate, 3-phenoxy-α-cyanobenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropane-1-carboxylate, 3-
Phenoxy-α-cyanobenzyl 2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-
Synthetic pyrethroids such as 1-carboxylate, 3-phenoxy-α-cyanobenzyl α-isopropyl-4-chlorophenylacetate and their various isomers or pyrethrum extract, o,o-diethyl-o-(3-oxo-2 -Phenyl-2H-pyridazin-6-yl) phosphorothioate (Mitsui Toatsu Chemical registered trademark Offnac)
, o,o-dimethyl-o-(2,2-dichlorovinyl)
-phosphate (DDVP), o,o-dimethyl-o-
(3-Methyl-4-nitrophenyl) phosphorothioate, thiazinon, o,o-dimethyl-o-4-cyanophenylphosphorothioate, o,o-dimethyl-s-
[α-(ethoxycarbonyl)benzyl]phosphorodithioate, 2-methoxy-4H-1,3,2-benzodioxaphosphorine-2-sulfide, o-ethyl-o-
Organophosphorus insecticides such as 4-cyanophenylphenylphosphonothioate, 1-naphthyl-N-methylcarbamate (NAC), m-tolyl-N-methylcarbamate (MTMC), 2-dimethylamino-5,6-dimethyl Carbamate insecticides such as pyrimidin-4-yl-dimethylcarbamate (pyrimer), 3,4-dimethylphenyl N-methylcarbamate, 2-isopropoxyphenyl N-methylcarbamate, 3-phenoxybenzyl 2-(4-chlorophenyl) -2-methylpropyl ether, 3-phenoxy-4-fluorobenzyl
2-(4-chlorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4-ethoxyphenyl)-2-methylpropyl ether, 3-phenoxy-4-fluorobenzyl 2-(4-ethoxyphenyl)- Arylpropyl ether insecticides such as 2-methylpropyl ether, other insecticides, acaricides or fungicides, nematicides, herbicides, plant growth regulators,
By mixing it with fertilizers, BT agents, insect hormones, other agricultural chemicals, etc., it is possible to create multipurpose compositions with even greater efficacy, and a synergistic effect can also be expected.

Furthermore, for example, α-[2-(2-butoxyethoxy)ethoxy]-4,5-methylenedioxy-2
-propyltoluene {piperonyl butoxide}, 1,
2-methylenedioxy-4-[2-(octylsulfinyl)propyl]benzene {sulfoxide}, 4-(
3,4-methylenedioxyphenyl)-5-methyl-1
, 3-dioxane {safloxane}, N-(2-ethylhexyl)-bicyclo(2,2,1)hept-5-ene-2,3-dicarboximide {MGK-264}, octachlorodipropyl ether {s -421}, isobornyl thiocyanoacetate {Garnite}, and other known synergists for pyrethroids can be added to increase its efficacy several times.

The compounds of the present invention have high stability against light, heat, oxidation, etc., but if necessary, antioxidants or ultraviolet absorbers, such as BHT (2,6-di-tert-butyl-
4-methylphenol), BHA (butylhydroxyanisole), phenol derivatives, bis-phenol derivatives, and arylamines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, condensates of phenetidine and acetone, or benzophenone. By adding an appropriate amount of such compounds as a stabilizer, a composition with more stable effects can be obtained.

[0385] The insecticide and acaricide of the compound of the present invention contains the compound in an amount of 0.0001 to 95% by weight, preferably 0.001 to 95% by weight.
Contain 50% by weight.

[0386] Next, some examples of formulations in which the compounds of the present invention are used as insecticides and acaricides are shown, but the present invention is not limited to these. All "parts" indicate polymerized parts.

0387]

[Formulation example 1. ] 20 parts of the compound of the present invention, Solpol 355
10 parts of S (a mixture of nonionic surfactant and anionic surfactant, registered trade name of Toho Chemical) and 70 parts of xylene are stirred and mixed to form an emulsion.

0388

[Formulation example 2. 1 part of the compound of the present invention is dissolved in 10 parts of acetone, 99 parts of clay for powders are added, and the acetone is evaporated to form a powder.

0389]

[Formulation example 3. ] Add 5 parts of a surfactant to 20 parts of the compound of the present invention and mix well, then add 75 parts of diatomaceous earth and mix with stirring in a Raikai machine to prepare a wettable powder.

0390]

[Formulation example 4. ] Meta-tolyl N to 0.2 part of the compound of the present invention
Add 2 parts of methyl carbamate, then add 0.2 parts of each PAP (isopropyl acid phosphate, registered trademark of Nippon Chemical Industries, physical property improver), dissolve in 10 parts of acetone, add 97.6 parts of powder clay, and place in a Raikai machine. If the mixture is stirred and the acetone is evaporated, it becomes a powder.

0391

[Formulation example 5. ] Add 2 parts of Offnac (Mitsui Toatsu Chemical registered product name) to 0.2 parts of the compound of the present invention, and then add PAP.
Add 0.2 parts of (mentioned above), dissolve in 10 parts of acetone, add 97.6 parts of powder clay, stir and mix in a laikai, and evaporate the acetone to obtain a powder.

0392]

[Formulation example 6. ] 0.5 part of piperonyl butoxide was added to 0.1 part of the compound of the present invention, dissolved in white kerosene, and the total amount was 100%.
%, it becomes an oil agent.

0393

[Formulation example 7. ] Add 5 parts of Solbol SM-200 (a mixture of nonionic surfactant and anionic surfactant, trade name of Toho Chemical Co., Ltd.) to 0.5 parts of the compound of the present invention and 5 parts of Offnac (mentioned above), and add xylol. When dissolved in 89.5 parts, it becomes an emulsion.

0394

[Formulation example 8. ] 0.4 parts of the compound of the present invention, 2.0 parts of piperonyl butoxide, 6 parts of xylene, and 7.6 parts of deodorized kerosene are mixed and dissolved, filled into an aerosol container, and after the valve part is attached, it is injected through the valve part. If 84 parts of the agent (liquefied petroleum gas) is filled under pressure, it will become an aerosol.

0395]

[Formulation example 9. ] Dissolve 0.05 g of the compound of the present invention in an appropriate amount of chloroform, and prepare a 2.5 cm x 1.5 cm, 0.3 m thick
When it is evenly adsorbed onto the surface of asbestos (m), it becomes a fiber fumigation insecticidal composition heated on a hot plate.

0396

[Formulation example 10. ] Dissolve 0.5 g of the compound of the present invention in 20 ml of methanol, stir and mix uniformly with 99.5 parts of an incense stick carrier (mixing tab flour: lees flour: wood flour in a ratio of 3:5:1), and mix with methanol. After evaporating, add 150 ml of water, mix thoroughly, mold and dry to make mosquito coil.

0397]

[Formulation example 11. ] 1 part of the compound of the present invention, 3 parts of Ofnac (mentioned above), Celogen 7A (carboxymethyl cellulose,
Daiichi Kogyo Seiyaku brand name) 2 parts, Sunextract (ligninsulfonic acid-Na salt, Sanyo Kokusaku pulp product), 2 parts clay 92
Granules are obtained by mixing these parts, adding water, granulating them, and sizing them to the optimum particle size.

[0398] When applying the compound of the present invention, the amount of the active ingredient is generally 300 to 1 g per 10 ares, preferably 100 to 2 g, more preferably 20 g to 1 g.
It is 5g.

Next, in order to clarify that the compounds of the present invention have excellent insecticidal and acaricidal effects and have low toxicity to fish, test examples are shown below.

[0400] As a comparative compound, the following (a)
Compounds (g) to (g) were prepared and tested in the same manner as the compounds of the present invention. All tests were conducted in duplicate, and the results are shown as the average value.

(a) DDVP, (b) Ofnac, (c) Diazinon, (d) Methomyl, (e) Kelsen, (f) PCP Sodium Salt, (g) Fenvalerate Pesticide Sci
ence Vol. 7, 241 (1977).

0402]

[Test example 1. Effect on Spodoptera trifoliata] Formulation example 1.
The emulsion of each test compound prepared above is diluted with water to a predetermined concentration, and sweet potato leaves are thoroughly immersed. After air-drying, the treated leaves were placed in a plastic cup with a diameter of 10 cm, and 10 3rd instar larvae of Spodoptera were released at a time, and their survival was examined 48 hours later.

[0403] The results are shown in Table 2 shown in Table 24 and Table 25 below. The test compounds are indicated by the compound numbers in Table 1 above (the same applies hereinafter).

0404]

[Table 24]

0405]

[Table 25]

0406]

[Test example 2. [Effect against black leafhopper] 4 to 5 paddy rice seedlings at the 3-leaf stage were tied together in Test Example 1. 3 ml of each test compound emulsion prepared in the same manner as above was sprayed. After air-drying, the seedlings were covered with a wire mesh cylinder, 10 adult female leafhoppers were released, and the number of dead insects was counted 48 hours later.

The results are shown in Table 3 shown in Table 26, Table 27 and Table 28 below.

0408]

[Table 26]

0409]

[Table 27]

0410]

[Table 28]

0411]

[Test example 3. Effect on German cockroach] Diameter 9c
1 ml of an acetone solution of each test compound at a predetermined concentration was added to a deep Petri dish with a height of 9 cm and the mixture was left standing to evaporate the acetone. To prevent insects from escaping, apply butter to the upper part of the inner wall of the petri dish, and add 10 female adult German cockroaches per petri dish.
The number of dead insects was counted 48 hours after each head was released.

The results are shown in Table 4 shown in Table 29 below.

0413]

[Table 29]

0414]

[Test example 4. Effect against two-spotted spider mites: Place a leaf disk (diameter 20 mm) of a green bean leaf on absorbent cotton moistened with water, and inoculate 20 adult female two-spotted spider mites. After standing for a day and night, 2 of the test compound prepared in the same manner as Test Examples 1 and 2.
3ml of 00ppm emulsion to a diameter of 20cm and a height of 60cm
The insects were sprayed using a spray tower, and the number of dead insects was counted 24 hours later.

The results are shown in Table 5 shown in Table 30 below.

0416]

[Table 30]

0417]

[Test example 5. Toxicity to fish] Width 60cm, height 30cm
Fill a tank with water at a depth of 40 cm, and release 10 old carp fish with a body length of about 5 cm to allow them to acclimate. An acetone solution of each test compound was added in an amount of 1/100 of the amount of water to make the concentration in water 1.0.1 ppm, and the number of living and dying and the effects were investigated at each elapsed time.

[0418] The results are shown in Table 6 shown in Table 35 and Table 36 below.

0419]

[Table 31]

0420]

[Table 32]

0421]

[Effect of the invention] The aromatic alkane derivative according to the present invention is
This is a new compound that has not yet been published in the literature, and has excellent insecticidal and acaricidal properties. Moreover, this compound has low toxicity not only to warm-blooded animals but also to fish, and is therefore extremely useful as a highly safe and low-toxicity insecticide.

Claims (7)

[Claims] [Claim 1] General formula (I) represented by the following chemical formula 1 [
Chemical formula 1] (wherein, Ar represents an optionally substituted phenyl group or naphthyl group, R1 represents a methyl group, ethyl group, or isopropyl group, R2 represents a hydrogen atom or a methyl group, and R1 and R2 are Together with the carbon atom to which they are attached, they may form an optionally substituted cycloalkyl group; R3 represents the alcoholic root group customarily used in the form R3OH in the case of natural and synthetic pyrethroids). Aromatic alkane derivatives represented. 2. In the compound according to claim 1, R
3 is represented by the following general formula (2), (3), (4), or (5).
II), (III), (IV), and (V), and R4 is a hydrogen atom, an ethynyl group, or is a cyano group, R
5 is an allyl group, a propargyl group, a benzyl group, a thenyl group, a furylmethyl group, a phenoxy group, a phenylmercapto group, a benzoyl group or a pyridyloxy group (these groups are optionally halogen, an alkyl group, an alkoxy group, a haloalkyl group, ), R6 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a haloalkyl group, a cyano group or a nitro group, and n is an integer of 1 to 4. , and when n is an integer of 2 or more, each of R6 is independently selected, A is an oxygen atom, a sulfur atom, or -CH=CH-, and R7 is a hydrogen atom, a methyl group, an alkoxy group. or represents a halogen atom, R8 is a phthalimide group, thiophthalimide group, di- or tetra-hydrophthalimide group, or dialkylmaleimide group (these groups may be optionally substituted), and R9 is an alkyl group, A compound characterized in that it is an alkenyl group, an alkynyl group, or an aralkyl group, and R10 is a hydrogen atom or a methyl group. 3. In the compound according to claim 1, R
3 is a group of general formula (VI) represented by the following chemical formula 6,
embedded image R4, R6 and n represent the above meanings, R11 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a haloalkyl group, a cyano group or a nitro group, and m represents an integer of 1 to 5; , and when m is an integer of 2 or more, each R11 is selected independently of the other. [Claim 4] General formula (VII
) [In the formula, Ar represents an optionally substituted phenyl group or naphthyl group, R1 represents a methyl group, ethyl group or isopropyl group, R2 represents a hydrogen atom or a methyl group, and R1 and R2 may form an optionally substituted cycloalkyl group together with the carbon atom to which they are bonded), and a ketone represented by the following formula (VIII) Here, R12 is R12CH in the case of a synthetic pyrethroid.
represents the alcoholic radical commonly used in the form 2OH)
is reacted with an aldehyde represented by the formula (IX) shown below: A saturated carbonyl compound is obtained, and the obtained ketone is reduced to obtain the general formula (I) represented by the following chemical formula 10. ,
In this case, R3 represents an R12CH2- group, and R12 represents the above-mentioned meaning). [Claim 5] General formula (X) represented by the following chemical formula 11
Formula 11 may form an optionally substituted cycloalkyl group together with the carbon atom to which they are bonded; In the case of synthetic pyrethroid, R12 is R12CH
represents the alcoholic radical commonly used in the form 2OH)
The following chemical formula 13 obtained by reacting with the ketone represented by
It is characterized by reducing an α,β-unsaturated carbonyl compound represented by the general formula (XII) [Chemical formula 13] (wherein Ar, R1, R2 and R12 have the above-mentioned meanings), General formula (I) represented by the following chemical formula (14) (wherein Ar, R1 and R2 represent the above meanings,
In this case, R3 represents an R12CH2- group, and R12 represents the above-mentioned meaning). [Claim 6] General formula (XI
II) [Formula 15] (wherein, Ar represents an optionally substituted phenyl group or naphthyl group, R1 represents a methyl group, ethyl group or isopropyl group, R2 represents a hydrogen atom or a methyl group, R1 and R2 may form an optionally substituted cycloalkyl group together with the carbon atom to which they are bonded, and an aldehyde represented by the following formula (XIV) or (
XV) [Chemical 16] [Chemical 17] (wherein, R12 is R12CH in the case of a synthetic pyrethroid
represents the alcoholic radical commonly used in the form 2OH,
R3 is R3OH in the case of natural and synthetic pyrethroids
represents the base group of an alcohol commonly used in the form of
is an alkyl group or a phenyl group, and R14 is an alkyl group, respectively.
VI) or (XVII) [Formula 18] [Formula 19] (wherein Ar, R1, R2, R12 and R3 represent the above-mentioned meanings) General formula (I) represented by 20 [
embedded image (wherein Ar, R1 and R2 represent the above meanings,
R3 is R3 in the case of natural and synthetic pyrethroids.
A method for producing an aromatic alkane derivative represented by (representing the commonly used alcoholic radical in the form of OH). [Claim 7] General formula (I) represented by the following chemical formula (21)
embedded image (wherein, Ar represents an optionally substituted phenyl group or naphthyl group, R1 represents a methyl group, ethyl group or isopropyl group, R2 represents a hydrogen atom or a methyl group, R1 and R2 together with the carbon atom to which they are attached may form an optionally substituted cycloalkyl group; R3 represents the alcoholic backbone customary in the case of natural and synthetic pyrethroids in the form R3OH) An insecticidal and acaricidal composition comprising an aromatic alkane derivative represented by the following as an active ingredient.