2-Arylpropyl ether or thioether derivatives and insecticidal and acaricidal agents containing said derivatives

The present invention relates to 2-arylpropyl ether or thioether derivatives represented by the following general formula [I]: ##STR1## wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula [II]: ##STR2## or the following general formula [III]: ##STR3## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R.sup.1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R.sup.1 may be the same or different, and also to processes for the preparation or these ethers of thioethers and a use of these ethers or thioethers. These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.

DETAILED DESCRIPTION OF THE INVENTION 
The present invention relates to novel 2-arylpropyl ether or thioether 
derivatives, processes for the preparation thereof, insecticidal and 
acaricidal agents containing these novel compounds, and an insecticidal 
and acaricidal method using these novel compounds. 
More specifically, in accordance with one aspect of the present invention, 
there are provided 2-arylpropyl ether or thioether derivatives represented 
by the following general formula [I]: 
##STR4## 
wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, 
Y stands for an oxygen or sulfur atom, and B stands for a group 
represented by the following formula [II]: 
##STR5## 
or the following general formula [III]: 
##STR6## 
wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene 
group, R.sup.1 stands for a hydrogen or halogen atom or a lower alkyl 
group or a lower alkoxy group, and n is an integer of from 1 to 5 with the 
proviso that when n is 2 or more, the groups R.sup.1 may be the same or 
different. 
In accordance with another aspect of the present invention, there are 
provided processes for the preparation of 2-arylpropyl ether or thioether 
derivatives represented by the above general formula [I], which comprises 
reacting a compound represented by the following general formula [V]: 
##STR7## 
with a compound represented by the following general formula [VI]: 
EQU B--CH.sub.2 --D [VI] 
wherein Ar, R and B are as defined above, and one of groups A and D stands 
for a halogen atom and the other group is a group Y--M in which Y is as 
defined above and M stands for a hydrogen atom or an alkali metal or 
alkaline earth metal atom or both A and D stand for a hydroxyl group. 
In accordance with still another aspect of the present invention, there are 
provided insecticidal and acaricidal agents comprising 2-arylpropyl ethers 
represented by the above general formula [I] and/or 2-arylpropyl 
thioethers represented by the above general formula [I]. 
In accordance with still another aspect of the present invention, there is 
provided an insecticidal and acaricidal method using 2-arylpropyl ether 
derivatives represented by the above general formula [I] and/or 
2-arylpropyl thioether derivatives represented by the above general 
formula [I]. 
Insecticides have taken very important roles in improving productivities in 
various fields of agriculture. Development of organic synthetic 
agricultural chemicals changed completely the food situation for man, and 
agricultural chemicals have made great contributions to prevention of 
infectious diseases through the medium of insect pests. 
However, uses of organochlorine insecticides represented by DDT and BHC are 
not limited because they are left in applied environments for a long time 
after application. Organophosphate insecticides and carbamate insecticides 
developed as substitutes for these organochlorine insecticides are now 
used widely in various fields, but a variety of insect pests having 
acquired resistances to these chemicals have already appeared and insect 
pests which can hardly be controlled grow in certain territories. The 
problem of control of chemical-resistant insect pests will expand and 
become serious. 
For the purpose of maintaining and developing civilization of the mankind 
established up to the present, it is important to continuously supply 
foods sufficiently and stably, and in order to attain this object, it is 
eagerly desired to develop chemicals having an excellent insecticidal 
activity. 
Under such background, synthetic pyrethroid insecticides have attracted 
attention, because they have an excellent insecticidal activity and are 
very effective for controlling insect pests having acquired resistances to 
organophosphate insecticides or carbamate insecticides while they have low 
toxicity to men and animals. However, these synthetic pyrethroid 
insecticides have a fatal defect in that the fish toxicity is very high, 
and the application ranges of these chemicals are strictly limited because 
of this fatal defect. Moreover, these synthetic pyrethroid insecticides 
are much more expensive than other synthetic insecticides heretofore 
developed. 
These defects should be eliminated in agricultural chemicals which will be 
developed for the future. More specifically, it is desired to develop 
insecticides which have a high safety, are readily decomposed without 
being left in applied environments, hence do not cause any environmental 
pollution, have a high activity of controlling insect pests having 
acquired a resistance to insecticides and are manufactured at low cost. 
Research has been made with a view to developing insecticidal and 
acaricidal agents satisfying the foregoing requirements, and it has been 
found that specific 2-arylpropyl ether or thioether derivatives have high 
insecticidal and acaricidal activities, are excellent in their fast-acting 
property and residual activity, are of low toxicity to not only men and 
animals but also fish and can be supplied at a relatively low cost. 
The present research has continued for obtaining active compounds and also 
for confirming insecticidal and acaricidal characteristics of these 
compounds, and it was found that according to an appropriate combination 
of two alcohol residues in the abovementioned ether or thioether 
derivatives, these compounds can posses selective and non-selective 
activities insect pests to belonging to orders of Coleoptera, Lepidoptera, 
Orthoptera, Hemiptera, Isoptera and Acarina and these compounds have a 
broad insecticidal spectrum and that very excellent insecticidal 
compositions having a very low toxicity to men and animals can be prepared 
from these compounds. It also was found that most of these compounds are 
very low in their toxicity to fishes. 
The present invention has now been completed based on these findings. 
The compounds of the present invention have an active structure quite 
different from those of the conventional agricultural chemicals. They have 
an excellent insecticidal activity to sanitary insect pests such as fly, 
mosquito and cockroach and agricultural insect pests such as planthoppers, 
leafhoppers, worms, moths, leaf holders, aphids, borers and mites, 
especially green rice leafhopper, and furthermore, they are effective for 
controlling stored grain insect pests such as grain mite, Indian meal moth 
and rice weevil, animal-parasitic mites and lice, and other insect pests. 
Furthermore, the compounds of the present invention are excellent in the 
fast-acting property and residual activity and have a flushing effect. 
Moreover, the compounds of the present invention have not only a 
knock-down effect to kill insect pests but also an repellent action of 
insect pests from hosts. Still further, the compounds of the present 
invention have submerged application effects and are advantageous in that 
the phytotoxicity to plants of Solanacede, which is observed in 
Fenvalerate, one of the typical instances of synthetic pyrethroids, is not 
observed at all. In addition, the compounds of their present invention are 
very low in the toxicity to mammals, and some of the compounds of the 
present invention have a high safety to fish and they are suitably applied 
for controlling insect pests in paddy fields and aquatic insect pests such 
as larvae of mosquitoes and gnats and also are used for aerial application 
over broad districts including lakes, marshes, ponds and rivers without a 
fear of extermination of fish. 
Accordingly, insecticidal and acaricidal compositions comprising the 
compounds of the present invention can be applied very widely in various 
fields and have a very high controlling effect to agricultural and 
horticultural insect pests, stored grain insects, sanitary insect pests, 
household insect pests, forest insect pests and aquatic insect pests. 
Moreover they are very safe and can be supplied at low cost in the form of 
various formulations. 
The 2-arylpropyl ether and thioether derivatives represented by the general 
formula [I] according to the present invention are novel compounds. The 
aryl group Ar includes aromatic hydrocarbon groups such as phenyl, 
naphthyl, anthryl and phenanthryl groups, which may be unsubstituted or 
substituted with the same or different substituents selected from the 
substituents described hereinafter. As the substituent, there can be 
mentioned, for example, a halogen atom, an alkyl group, a haloalkyl group, 
a phenyl group, an alkoxy group, a haloalkoxy group, a cycloalkoxy group, 
a phenoxy group, an alkenyl group, a haloalkenyl group, an alkynyl group, 
a haloalkynyl group, an alkoxyalkyl group, an alkenyloxy group, a 
haloalkenyloxy group, an alkynyloxy group, a haloalkynyloxy group, an 
alkylthio group, a haloalkylthio group, an alkylsulfoxyl group, an acyl 
group, an alkoxyalkoxy group, an alkenylthio group, an alkoxycarbonyl 
group, a haloalkoxycarbonyl group, an alkynyloxycarbonyl group, an 
alkenyloxycarbonyl group, a nitro group, a nitrile group, a 
haloalkenylthio group, a methylenedioxy group, a 
3,4-difluoromethylenedioxy group, a 3,4-difluoroethylenedioxy group, a 
3,4-trifluoroethylenedioxy group and a polymethylene group having 3 to 5 
carbon atoms. From the industrial viewpoint, unsubstituted aryl groups and 
mono- and poly-substituted aryl groups having same or different 
substituents selected from a halogen atom, a lower alkyl group, a lower 
haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a 
methylenedioxy group, a lower alkylthio group, a nitrile group and a nitro 
group are preferred. 
Specific examples of the aryl group are mentioned below though aryl groups 
that can be used in the present invention are not limited to those 
exemplified below. As specific examples of the aryl group, there can be 
mentioned a phenyl group, a 4-methylphenyl group, a 3,4-dimethylphenyl 
group, a 4-trifluoromethylphenyl group, a 3-methylphenyl group, a 
3-trifluoromethylphenyl group, a 4-chlorophenyl group, a 
3,4-dichlorophenyl group, a 4-nitrophenyl group, a 4-methylthiophenyl 
group, a 4-methoxyphenyl group, a 3,4-dimethoxyphenyl group, a 
3,4-methylenedioxyphenyl group, a 4-difluoromethylthiophenyl group, a 
4-trifluoromethylthiophenyl group, a 3,4-difluoromethylenedioxyphenyl 
group, a 4-cyanophenyl group, a 4-fluorophenyl group, a 4-bromophenyl 
group, a 3,4-difluorophenyl group, a 3,4-dibromophenyl group, a 
4-chloro-3-fluorophenyl group, a 3-chloro-4-fluorophenyl group, a 
3-chloro-4-methylphenyl group, a 3-bromo-4-chlorophenyl group, a 
4-difluoromethoxyphenyl group, a 3,4-bis(difluoromethoxy)phenyl group, a 
4-trifluoromethoxyphenyl group, a 3,4-bis(trifluoromethoxy)phenyl group, a 
4-methoxy-3,5-dimethylphenyl group, a 3,4-trifluoroethylenedioxyphenyl 
group, a 4-tert-butylphenyl group, a 4-ethylphenyl group, a 
4-isopropylphenyl group, a 3,4-difluoroethylenedioxyphenyl group, a 
4-isopropenylphenyl group, a 4-vinylphenyl group, a 
4-(2,2-dichlorovinyl)phenyl group, a 4-chloro-3-methylphenyl group, a 
3-bromo-4-fluorophenyl group, 2-naphthylgroup, a 3-fluoro-4-bromophenyl 
group, a 4-fluoro-3-methylphenyl group, a 3-fluoro-4-methylphenyl group, a 
3-bromo-4-methylphenyl group, a 3,4-diethylphenyl group, a 
3,4-diisopropylphenyl group, a 3-ethyl-4-methylphenyl group, a 
4-isopropyl-3-methylphenyl group, a 4-methoxymethoxyphenyl group, a 
4-methylsulfoxyphenyl group, a 4-allylphenyl group, a 4-acetylphenyl 
group, a 4-carboethoxyphenyl group, a 4-ethoxyphenyl group, a 
1,2,3,4-tetrahydronaphthalen-7-yl group, a 3,5-dichloro-4-methylphenyl 
group, an indan-5-yl group, a 4-propargylphenyl group, a 
3-methoxy-4-methylphenyl group, a 4-methoxymethylphenyl group, a 
4-(1-chloroethylen-1-yl)phenyl group, a 4-(2-chloroallyl)phenyl group, a 
4-isobutyrylphenyl group, a 4-carbomethoxyphenyl group, a 
3-nitro-4,5-dimethylphenyl group, a 3-ethoxy-4-bromophenyl group, a 
3-chloro-4-methoxyphenyl group, a 4-bromo-3-chlorophenyl group, a 
3,4-(di-tert-butyl)phenyl group, a 4-ethyl-3-methylphenyl group, a 
4-tert-butyl-3-methylphenyl group, a 4-(1,1,2,2-tetrafluoroethoxy)phenyl 
group, a 4-(2,2-dichlorovinyloxy)phenyl group, a 
4-(2,2,2-trifluoroethoxy)phenyl group, a 4-pentafluoroethoxyphenyl group, 
a 4-(chlorodifluoromethoxy)phenyl group, a 4-(chlorofluoromethoxy)-phenyl 
group, a 4-dichlorofluoromethoxy phenyl group, a 
4-(1,1-difluoroethoxy)phenyl group, a 
4-(1,2,2-trichloro-1,2-difluoroethoxy)phenyl group, a 
4-(2-bromo-1,1,2,2-tetrafluoroethoxy)phenyl group, a 
4-(2-propynyloxy)phenyl group, a 4-(1-propynyloxy)phenyl group, a 
4-allyloxyphenyl group, a 4-ethynyloxyphenyl group, a 
4-(2-chloroethynylene)phenyl group, a 4-(n-propoxy)phenyl group, a 
4-(isopropoxy)phenyl group, a 4-cyclopentyloxyphenyl group, a 
4-(n-pentyloxy)phenyl group, a 4-isobutoxy phenyl group, a 4-iodophenyl 
group, a 4-vinyloxyphenyl group, a 4-biphenyl group, a 4-(n-butoxy)phenyl 
group, a 4-(sec-butoxy)phenyl group, a 6-methyl-2-naphthyl group, a 
4-phenoxyphenyl group, a 4-(2-iodo-1,1-difluoroethoxy)-phenyl group, a 
4-cyclohexyloxyphenyl group, a 3-chloro-4-ethoxyphenyl group, a 
4-ethoxymethoxyphenyl group, a 4-ethoxymethylphenyl group, a 
4-ethoxyethoxyphenyl group, a 4-(1-ethoxyethyl)phenyl group, a 
4-(1-methoxyethyl)phenyl group, a 4-ethoxy-3-methylphenyl group, a 
4-(2-methyl-1-propenyl)phenyl group, a 4-(1,2,2-trichlorovinyloxy)phenyl 
group, a 3,4-diethoxyphenyl group, a 4-ethynylphenyl group, a 
4-ethoxy-3,5-dimethylphenyl group, a 4-ethoxy-3-methoxyphenyl group, a 
4-ethythiophenyl group, a 4-(2,2,2-trifluoroethoxycarbonyl)phenyl group, a 
4-(2-chloroethoxy)-phenyl group, a 4-(1-buten-2-yl)phenyl group and a 4 
-(2-buten-2-yl)phenyl group, a 4-vinylphenyl group. 
As specific examples of the group B--CH.sub.2 --, there can be mentioned a 
5-benzyl-3-furylmethyl group, a 3-phenoxybenzyl group, a 
3-(4-fluorophenoxy)benzyl group, a 3-(4-bromophenoxy)benzyl group, a 
3-(4-chlorophenoxy)benzyl group, a 3-(3-fluorophenoxy)benzyl group, a 
3-(2-bromophenoxy)benzyl group, a 3-(3-chlorophenoxy)benzyl group, a 
3-(4-methylphenoxy)benzyl group, a 3-(2-fluorophenoxy)-benzyl group, a 
3-(2-chlorophenoxy)-benzyl group, a 3-(3-bromophenoxy)benzyl group, a 
3-(3-methoxyphenoxy)benzyl group, a 3-(2-methylphenoxy)benzyl group, a 
3-(4-ethoxyphenoxy)benzyl group, a 3-(4-methoxyphenoxy)benzyl group, a 
3-(3-methylphenoxy)benzyl group, a 3-(2-methoxyphenoxy)benzyl group, a 
3-phenylthiobenzyl group, a 3-benzoylbenzyl group, a 3-benzylbenzyl group, 
a 3-(4-chlorobenzyl)benzyl group, a 3-(4-fluorobenzyl)-benzyl group, a 
3-(3,5-dichlorophenoxy)benzyl group, a 3-(3,4-dichlorophenoxy)benzyl 
group, a 3-(4-chloro-2-methylphenoxy)benzyl group, a 
3-(2-chloro-5-methylphenoxy)-benzyl group, a 
3-(4-chloro-3-methylphenoxy)benzyl group, a 3-(4-ethylphenoxy)benzyl 
group, a 3-(3-chloro-5-methoxyphenoxy)benzyl group, a 
3-(4-fluorophenylthio)benzyl group, a 3-(3-fluorophenylthio)benzyl group, 
a 3-(3,5-dichlorobenzoyl)benzyl group, a 3-(3,4-dichlorobenzoyl)benzyl 
group, a 3-(2,5-dichlorobenzoyl)benzyl group and a 
3-(4-methylbenzyl)benzyl group. 
Typical examples of the compounds according to the present invention will 
now be described. Of course, the compounds included in the scope of the 
present invention are not limited to those exemplified below. 
Incidentally, in the case where R in the general formula [I] is an ethyl 
group, the compounds contain an asymmetric carbon atom and there are 
present optical isomers. These optical isomers and mixtures thereof are 
included in the scope of the present invention. 
Examples of the compounds included in the scope of the present invention 
are as follows. 
3-Phenoxybenzyl 2-(4-methoxyphenyl)-2-methyl propyl ether and thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-fluorophenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-methoxyphenyl)-2-ethylpropyl ether and thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-fluorophenyl)-2-methylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-methylphenyl)-2-methylpropyl ether and 
thioether 
3-(4-Bromophenoxy)benzyl 2-(4-chlorophenyl)-2-methylpropyl ether and 
thioether 
3-(4-Bromophenoxy)benzyl 2-(4-chlorophenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-phenyl-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-phenyl-2-ethylpropyl ether and thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-chlorophenyl)-2-methylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-chlorophenyl)-2-ethylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(3,4-dimethylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3,4-methylenedioxyphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3,4-methylenedioxyphenyl)-2-ethylpropyl ether and 
thioether 
3-(4-Methoxyphenoxy)benzyl 2-(4-methylthiophenyl)-2-methylpropyl ether and 
thioether 
3-(3-Chlorophenoxy)benzyl 2-(4-chlorophenyl)-2-methylpropyl ether and 
thioether 
3-(3-Chlorophenoxy)benzyl 2-(4-chlorophenyl)-2-ethylpropyl ether and 
thioether 
3-(3-Fluorophenoxy)benzyl 2-(4-chlorophenyl)-2-methylpropyl ether and 
thioether 
3-(3-Fluorophenoxy)benzyl 2-(4-chlorophenyl)-2-ethylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-difluoromethoxyphenyl)-2-methylpropyl ether 
and thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-difluoromethoxyphenyl)-2-ethylpropyl ether 
and thioether 
5-Benzyl-3-furylmethyl 2-(4-chlorophenyl)-2-methylpropyl ether and 
thioether 
5-Benzyl-3-furylmethyl 2-(4-chlorophenyl)-2-ethylpropyl ether and thioether 
3-(4-methoxyphenoxy)benzyl 2-phenyl-2-methylpropyl ether and thioether 
3-(4-Methoxyphenoxy)benzyl 2-phenyl-2-ethylpropyl ether and thioether 
3-(2-Fluorophenoxy)benzyl 2-(4-chlorophenyl)-2-methylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(3-chloro-4-methylphenyl)-2-methylpropyl ether 
and thioether 
3-Phenylthiobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-trifluoromethylthiophenyl)-2-methylpropyl ether and 
thioether 
3-(4-Bromophenoxy)benzyl 2-(4-fluorophenyl)-2-ethylpropyl ether and 
thioether 
3-(4-Bromophenoxy)benzyl 2-(4-fluorophenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-trifluoromethylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-trifluoromethylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-trifluoromethylthiophenyl)-2-ethylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(3,4-dichlorophenyl)-2-methylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(3,4-dichlorophenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-difluoromethoxyphenyl)-2-methylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-difluoromethylthiophenyl)-2-methylpropyl 
ether and thioether 
3-Phenoxybenzyl 2-(4-difluoromethoxyphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3,4-dimethoxyphenyl)-2-methylpropyl ether and thioether 
3-(4-Chlorophenoxy)benzyl 2-(4-cyanophenyl)-2-methylpropyl ether and 
thioether 
3-(3-Fluorophenoxy)benzyl 2-(3,4-difluorophenyl)-2-ethylpropyl ether and 
thioether 
3-(4-Methylphenoxy)benzyl 2-(4-chlorophenyl)-2-methylpropyl ether and 
thioether 
3-(4-Methylphenoxy)benzyl 2-(4-chlorophenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether 
3-(2-Bromophenoxy)benzyl 2-(3,4-dibromophenyl)-2-methylpropyl ether and 
thioether 
3-(2-Chlorophenoxy)benzyl 2-(4-trifluoromethoxyphenyl)-2-methylpropyl ether 
and thioether 
3-(3-Methoxyphenoxy)benzyl 2-(4-ethylphenyl)-2-methyl-propyl ether and 
thioether 
3-(2-Methylphenoxy)benzyl 2-(4-isopropylphenyl)-2-methylpropyl ether and 
thioether 
3-(4-Bromophenoxy)benzyl 2-(3,4-dichlorophenyl)-2-methylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-trifluoromethylthiophenyl)-2-methylpropyl 
ether and thioether 
3-(4-Bromophenoxy)benzyl 2-(3,4-dichlorophenyl)-2-ethylpropyl ether and 
thioether 
3-(3-Bromophenoxy)benzyl 
2-(1,2,3,4-tetrahydronaphthalen-7-yl)-2-methylpropyl ether and thioether 
3-(4-Chlorobenzyl)benzyl 2-(4-ethoxyphenyl)-2-methylpropyl ether and 
thioether 
3-(3,5-Dichlorophenoxy)benzyl 2-(indan-5-yl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-difluoromethylthiophenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-difluoromethylthiophenyl)-2-ethylpropyl ether and 
thioether 
3-Benzoylbenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether 
3-Benzoylbenzyl 2-(4-chlorophenyl)-2-ethylpropyl ether and thioether 
3-(4-Fluorophenoxy)benzyl 2-(3-trifluoromethylphenyl)-2-methylpropyl ether 
and thioether 
3-(3-Fluorophenylthio)benzyl 2-(3-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4methylthiophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-methylthiophenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-pentafluoroethoxyphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3,4-difluoromethylenedioxyphenyl)-2-methylpropyl ether 
and thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-pentafluoroethoxyphenyl)-2-methylpropyl 
ether and thioether 
3-(3-Chlorophenoxy)benzyl 2-(4-difluoromethoxyphenyl)-2-methylpropyl ether 
and thioether 
3-(3-Chlorophenoxy)benzyl 2-(4-difluoromethoxyphenyl)-2-ethylpropyl ether 
and thioether 
3-(4-Chloro-2-methylphenoxy)benzyl 2-(4-allylphenyl)-2-methylpropyl ether 
and thioether 
3-(3,5-Dichlorobenzoyl)benzyl 2-(4-tert-butylphenyl)-2-methylpropyl ether 
and thioether 
3-(4-Chlorophenoxy)benzyl 2-(3-chloro-4-fluorophenyl)-2-methylpropyl ether 
and thioether 
3-(3-Methylphenoxy)benzyl 2-(4-chlorophenyl)-2-methylpropyl ether and 
thioether 
3-(3-Methylphenoxy)benzyl 2-(4-chlorophenyl)-2-ethylpropyl ether and 
thioether 
3-(2-Methoxyphenoxy)benzyl 2-(4-methoxymethylphenyl)-2-methylpropyl ether 
and thioether 
3-(4-Methoxyphenoxy)benzyl 2-(4-methoxyphenyl)-2-methylpropyl ether and 
thioether 
3-(3-Bromophenoxy)benzyl 2-(3-methoxy-4-methylphenyl)-2-methylpropyl ether 
and thioether 
3-(4-Fluorobenzyl)benzyl 2-(4-chlorophenyl)-2-methylpropyl ether and 
thioether 
3-(3,4-Dichlorophenoxy)benzyl 2-(4-isobutyrylphenyl)-2-methylpropyl ether 
and thioether 
3-(4-Fluorophenoxy)benzyl 2-phenyl-2-methylpropyl ether and thioether 
3-(4-Fluorophenoxy)benzyl 2-phenyl-2-ethylpropyl ether and thioether 
3-(3-Chloro-5-methoxyphenoxy)benzyl 
2-[(3,4-di-tert-butyl)phenyl]-2-methylpropyl ether and thioether 
3-(3-Chlorophenoxy)benzyl 2-(3-methylphenyl)-2-methylpropyl ether and 
thioether 
3-(4-Fluorophenylthio)benzyl 2-(4-chlorophenyl)-2-methylpropyl ether and 
thioether 
3-(4-Bromophenoxy)benzyl 2-(4-difluoromethoxyphenyl)-2-methylpropyl ether 
and thioether 
3-(4-Bromophenoxy)benzyl 2-(4-difluoromethoxyphenyl)-2-ethylpropyl ether 
and thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-tert-butylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(2-naphthyl)-2-methylpropyl ether and thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-isopropenylphenyl)-2-methylpropyl ether and 
thioether. 
3-Phenoxybenzyl 2-(2-naphthyl)-2-ethylpropyl ether and thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-methoxyphenyl)-2-methylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-methoxyphenyl)-2-ethylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-chloro-3-methylphenyl)-2-methylpropyl ether 
and thioether 
3-Phenoxybenzyl 2-[3,4-bis(trifluoromethoxy)phenyl]-2-methylpropyl ether 
and thioether 
3-Phenoxybenzyl 2-(4-methoxy-3,5-dimethylphenyl)-2-methylpropyl ether and 
thioether 
3-(4-Bromophenoxy)benzyl 2-(4-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(2,2-dichlorovinyloxy)phenyl]-2-methylpropyl ether and 
thioether 
3-(4-Methoxyphenoxy)benzyl 2-(4-chlorophenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2-methylpropyl 
ether and thioether 
3-Benzylbenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-[4-(1,1,2,2-tetrafluoroethoxy)-phenyl]-2-ethylpropyl 
ether and thioether 
3-(4-Fluorophenoxy)benzyl 2-(3-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-chlorophenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3,4-dichlorophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3,4-dichlorophenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-chloro-3-bromophenyl)-2-methylpropyl ether and 
thioether 
3-(3-Chlorophenoxy)benzyl 2-(3,4-dichlorophenyl)-2-methylpropyl ether and 
thioether 
3-(3-Chlorophenoxy)benzyl 2-(3,4-dichlorophenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-chloro-3-bromophenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(2,2,2-trifluoroethoxy)phenyl]-2-methylpropyl ether 
and thioether 
3-Phenoxybenzyl 2-[4-(2,2,2-trifluoroethoxy)phenyl]-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-trifluoromethylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-chloro-4-methoxyphenyl)-2-methylpropyl ether and 
thioether 
3-(4-Methoxyphenoxy)benzyl 2-(4-bromophenyl)-2-methylpropyl ether and 
thioether 
3-(4-Methoxyphenoxy)benzyl 2-(3,4-dichlorophenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(6-methyl-2-naphthyl)-2-methylpropyl ether and thioether 
3-(4-Fluorophenoxy)benzyl 2-(3-bromo-4-chlorophenyl)-2-methylpropyl ether 
and thioether 
3-Phenoxybenzyl 2-[4-(2,2-dichlorovinyl)phenyl]-2-methylpropyl ether and 
thioether 
3-(4-Bromophenoxy)benzyl 2-(3-trifluoromethylphenyl)-2-methylpropyl ether 
and thioether 
3-Phenoxybenzyl 2-(4-nitrophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-nitrophenyl)-2-ethylpropyl ether and thioether 
3-(4-Fluorophenoxy)benzyl 2-(3-fluoro-4-methylphenyl)-2-methylpropyl ether 
and thioether 
3-(4-Methoxyphenoxy)benzyl 2-(4-methylphenyl)-2-methylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(3,4-diethylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-dichlorofluoromethoxyphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-dichlorofluoromethoxyphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-methylphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-bromophenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3-chloro-4-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3,4-dibromophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-tert-butylphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-fluorophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-bromophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-ethylphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-fluorophenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3-chloro-4-fluorophenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-ethylphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-chloro-3-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-tert-butylphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3,4-dimethylphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3-chloro-4-methylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3,4-dibromophenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-chloro-3-methylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3,4-dimethylphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-methylphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3-chloro-4-fluorophenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3,4-difluorophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3,4-difluorophenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3-bromo-4-fluorophenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-bromo-4-fluorophenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-fluoro-4-bromophenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-fluoro-4-bromophenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-bromo-3-chlorophenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-bromo-3-chlorophenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-fluoro-3-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-fluoro-3-methylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-fluoro-4-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-fluoro-4-methylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-bromo-4-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-bromo-4-methylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3,4-diethylphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3,4-diethylphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-isopropylphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-isopropylphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3,4-diisopropylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3,4-diisopropylphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3,4-di-tert-butylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3,4-di-tert-butylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-ethyl-4-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-ethyl-4-methylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-ethyl-3-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-ethyl-3-methylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-tert-butyl-3-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-tert-butyl-3-methylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-isopropyl-3-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-isopropyl-3-methylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-cyanophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-cyanophenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-ethoxyphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-ethoxyphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3,5-dichlorophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3,5-dichlorophenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-[4-(n-propoxy)phenyl]-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-[4-(n-propoxy)phenyl]-2-ethylpropyl ether and thioether 
3-(4-Fluorophenoxy)benzyl 2-(3-chloro-4-fluorophenyl)-2-methylpropyl ether 
and thioether 
3-(4-Fluorophenoxy)benzyl 2-(3-chloro-4-fluorophenyl)-2-ethylpropyl ether 
and thioether 
3-Phenoxybenzyl 2-(4-isopropoxyphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-isopropoxyphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-acetylphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-acetylphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-cyclopentyloxyphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-cyclopentyloxyphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(n-pentyloxy)phenyl]-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(n-pentyloxy)phenyl]-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-isobutyloxyphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-isobutyloxyphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-iodophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-iodophenyl)-2-ethylpropyl ether and thioether 
3-(4-Bromophenoxy)benzyl 2-(4-ethoxyphenyl)-2-methylpropyl ether and 
thioether 
3-(4-Bromophenoxy)benzyl 2-(4-ethoxyphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-vinyloxyphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-vinyloxyphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-biphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-biphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-[4-(n-butoxy)phenyl]-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-[4-(n-butoxy)phenyl]-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-[4-(sec-butoxy)phenyl]-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-[4-(sec-butoxy)phenyl]-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-phenoxyphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-phenoxyphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-cyclohexyloxyphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-cyclohexyloxyphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-[4-(1,1-difluoro-2-iodoethoxy)phenyl]-2-methylpropyl 
ether and thioether 
3-Phenoxybenzyl 2-[4-(1,1-difluoro-2-iodoethoxy)phenyl]-2-ethylpropyl ether 
and thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-isopropylphenyl)-2-methylpropyl ether and 
thioether 
3-(4-Fluorophenoxy)benzyl 2-(4-isopropylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-chloro-4-ethoxyphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3-chloro-4-ethoxyphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(1,1-difluoroethoxy)phenyl]-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(1,1-difluoroethoxy)phenyl]-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-methoxymethylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxyphenyl 2-(4-methoxymethylphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-ethoxymethoxyphenyl)-4-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-ethoxymethoxyphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-ethoxymethylphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-ethoxymethylphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-methoxymethoxyphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-methoxymethoxyphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(1-ethoxyethyl)phenyl]-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(1-ethoxyethyl)phenyl]-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-carboethoxyphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-carboethoxyphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2[4-(1-methoxyethyl)phenyl]-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(1-methoxyethyl)phenyl]-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-isopropenylphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-isopropenylphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-[4-(2-ethoxyethoxy)phenyl]-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-4-(2-ethoxyethoxy)phenyl-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-ethoxy-3-methylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-ethoxy-3-methylphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(2-methyl-propenyl)phenyl]-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(2-methyl-propenyl)phenyl]-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[(1,2,2-trichlorovinyloxy)phenyl]-2-methylpropyl ether 
and thioether 
3-Phenoxybenzyl 2-[(1,2,2-trichlorovinyloxy)phenyl]-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(3,4-diethoxyphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(3,4-diethoxyphenyl)-2-ethylpropyl ether and thioether 
3-(4-Ethoxyphenoxy)benzyl 2-(4-chlorophenyl)-2-methylpropyl ether and 
thioether 
3-(4-Ethoxyphenoxy)benzyl 2-(4-chlorophenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-ethynylphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-ethynylphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-ethoxy-3,4-dimethylphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-ethoxy-3,4-dimethyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-propargyloxyphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-propargyloxyphenyl)-2-ethylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-ethoxy-3-methoxyphenyl)-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-ethoxy-3-methoxyphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-ethylthiophenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-(4-ethylthiophenyl)-2-ethylpropyl ether and thioether 
3-(4-Ethoxyphenoxy)benzyl 2-(4-ethoxyphenyl)-2-methylpropyl ether and 
thioether 
3-(4-Ethoxyphenoxy)benzyl 2-(4-ethoxyphenyl)-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(1-chlorovinyl)phenyl]-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(1-chlorovinyl)phenyl]-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-(4-vinylphenyl)-2-methylpropyl ether and thioether 
3-Phenoxybenzyl 2-[4-(2,2,2-trifluoroethoxycarbonyl)-phenyl]-2-methylpropyl 
ether and thioether 
3-Phenoxybenzyl 2-[4-(2,2,2-trifluoroethoxycarbonyl)-phenyl]-2-ethylpropyl 
ether and thioether 
3-Phenoxybenzyl 2-[4-(2-chloroethoxy)phenyl]-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(2-chloroethoxy)phenyl]-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(1-buten-2-yl)phenyl]-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(1-buten-2-yl)phenyl]-2-ethylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(2-buten-2-yl)phenyl]-2-methylpropyl ether and 
thioether 
3-Phenoxybenzyl 2-[4-(2-buten-2-yl)phenyl]-2-ethylpropyl ether and 
thioether 
The preparation processes of the present invention will now be described in 
detail. 
In the case where an alcohol or thiol of the general formula [V] in which A 
stands for Y-H (in which Y is as defined above) is reacted with a halide 
of the general formula [VI] in which D stands for a halogen atom, the 
reaction is carried out in the presence of a base as an acid acceptor in 
an appropriate solvent at room temperature or under heating to give a 
desired. 2-arylpropyl ether or thioether derivative. As the base, there 
can be mentioned an alkali metal hydroxide, an alkaline earth metal 
hydroxide, an alkali metal hydride, an alkali metal alcoholate, an alkali 
metal oxide, an alkali metal carbonate, sodium amide and triethylamine. 
Furthermore, silver oxide may be used as the acid acceptor. As the 
solvent, there can be used, for example, water, aromatic hydrocarbons such 
as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane, 
heptane and petroleum, benzin, halogenated hydrocarbons such as chloroform 
and dichloromethane, aprotic polar solvents such as dimethylformamide and 
dimethylsulfoxide, ethers such as diisopropyl ether, diethyl ether, 
1,2-dimethoxyethane, tetrahydrofuran and dioxane, nitriles such as 
acetonitrile and propionitrile, and ketones such as diisopropyl ketone. If 
a phase transfer catalyst represented by tetra-n-butyl ammonium bromide or 
triethylbenzyl ammonium chloride is used as the catalyst, the intended 
2-arylpropyl ether or thioether derivative can be obtained in a high 
yield. 
In the case where an alcoholate or thioalcoholate of the general formula 
[V] in which A stands for a group Y-M (in which Y is as defined above and 
M is other than hydrogen) is reacted with a halide of the general formula 
[VI] in which D stands for a halogen atom, the reaction is carried out in 
a solvent as mentioned above at room temperature or under heating to give 
a desired 2-arylpropyl ether or thioether derivative. When the reactivity 
is low, a catalytic amount of potassium iodide or copper iodide is 
preferably added. 
In the case where a halide of the general formula [V] in which A stands for 
a halogen atom is reacted with an alcohol or thiol or alcoholate or 
thioalcoholate of the general formula [VI] in which D stands for a group 
Y-M (in which Y and M are as defined above), the reaction can be carried 
out according to the same procedures as described above. Especially when a 
halide of the general formula [V] in which A stands for a halogen atom is 
reacted with an alcohol or thiol of the general formula [VI] in which D 
stands for Y-H (in which Y is as defined above), the reaction is carried 
out in the presence of a base as an acid acceptor in an aprotic polar 
solvent, preferably dimethylsulfoxide or sulfolane, under heating, whereby 
a desired 2-arylpropyl ether or thioether derivative can be obtained in a 
high yield. 
In the case where an alcohol of the general formula [V] in which A stands 
for a hydroxyl group is reacted with an alcohol of the general formula 
[VI] in which D stands for a hydroxyl group, dehydration reaction is 
carried out in the presence of a catalyst to give a 2-arylpropyl ether 
derivative. As the catalyst, there may be employed an acid catalyst such 
as sulfuric acid, hydrochloric acid, an aromatic sulfonic acid, sulfonyl 
chloride, boron trifluoride or aluminum chloride. Furthermore, there may 
be used iodine, a solid acid catalyst (aluminatitanium oxide or the like), 
dimethylsulfoxide, alumina, a sulfide or an ion exchange resin as the 
dehydrating catalyst. The reaction is preferably carried out under reflux 
in an inert solvent azeotropic with water, such as benzene or toluene, 
according to need. 
Furthermore, a 2-arylpropyl ether derivative can be obtained by reacting an 
alcohol of the general formula [V] in which A stands for a hydroxyl group 
with an alcohol of the general formula [VI] in which D stands for a 
hydroxyl group in the presence of a dehydrating agent, if necessary in the 
presence of a catalyst. As the dehydrating agent, there is preferably used 
an N,N-substituted carbodiimide, especially N,N-dicyclohexylcarbodiimide. 
For example, cuprous chloride is preferably used as the catalyst. The 
reaction is carried out in an appropriate inert solvent or diluent at room 
temperature or under heating. As the solvent or diluent, there may 
preferably be used ethers such as 1,2-diethoxyethane, dioxane and 
tetrahydrofuran, aprotic polar solvents such as dimethylformamide, 
hexamethylphosphoric triamide and dimethylsulfoxide, and ketones such as 
acetone, methylethyl ketone and cyclohexanone. 
As another process for the preparation of 2-arylpropyl ether derivatives, 
there can be mentioned a process in which a metal alcoholate or sulfonic 
acid ester of an alcohol of the general formula [V] in which A stands for 
a hydroxyl group is reacted with an alcohol of the general formula [VI] in 
which D stands for a hydroxyl group, and a process in which an alcohol of 
the general formula [V] in which A stands for a hydroxyl group is reacted 
with a metal alcoholate or sulfonic acid ester of an alcohol of the 
general formula [VI]. However, these processes are disadvantageous from 
the viewpoint of the yield of the desired product compound. 
The starting substance represented by the general formula [V] can be 
prepared according to a known process or a process similar to a known 
process disclosed in a reference. For example, an alcohol represented by 
the general formula [V] in which A stands for a hydroxyl group can be 
obtained by alkylating a corresponding arylacetonitrile of the formula 
Ar.CH.sub.2.CN, in which Ar is as defined above, with a halogenated alkyl 
compound, hydrolyzing the obtained nitrile to a corresponding carboxylic 
acid and reducing the carboxylic acid. Furthermore, a halogenated compound 
of the general formula [V] in which A stands for a halogen atom, obtained 
by adding a 2-alkylallyl halide to an aryl compound, can be converted to 
an alcohol as mentioned above. 
The preparation routes are diagrammatically shown below. 
##STR8## 
Then, the preparation route (1) is adopted. 
##STR9## 
Furthermore, an alcohol of the general formula [V] in which A stands for a 
hydroxyl group may be prepared according to the process disclosed in 
Helvetica Chimica Acta, 54, 868 (1971). 
A metal alcoholate or metal thioalcoholate of the general formula [V] in 
which A stands for a group Y-M in which Y is as defined above and M is 
other than hydrogen can easily be prepared according to a conventional 
method for example, a process comprising reacting an alcohol or thiol of 
the general formula [V] in which A stands for a group Y-M in which Y is as 
defined above and M is a hydrogen atom with a metal hydride such as sodium 
hydride. 
An alcohol of the general formula [VI] in which B stands for a hydroxyl 
group is known as an alcohol component of a synthetic pyrethroid or it may 
be prepared according to a known process disclosed in a reference. A thiol 
of the general formula [VI] in which D stands for Y-H in which Y stands 
for a sulfur atom is prepared from a corresponding alcohol according to a 
conventional method. 
The process for the preparation of 2-arylpropyl ether and thioether 
derivatives of the present invention will now be described in detail with 
reference to the following Synthesis Examples.