JPH0368841B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula (In the formula, is an integer from 1 to 3, and R ₁ is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower haloalkyl group, a lower haloalkoxy group, a phenoxy group, an ethynyl group, a methylene Represents a dioxy group, nitrile group or nitro _group.R2 represents a hydrogen atom, a cyano group, an ethynyl group, a methyl group or a 1-propynyl group,
R ₃ represents a hydrogen atom or a fluorine atom, and R ₄ represents a group represented by the general formula (), (), or (). A here represents an oxygen atom or a methylene group. Z
is a nitrogen atom or a methine group, X is a hydrogen atom,
Indicates a halogen atom, methyl group, methoxy group, trifluoromethyl group or ethynyl group. R ₅ represents a hydrogen atom or a methyl group, and Y represents a hydrogen atom, a methyl group, a halogen atom, or a trifluoromethyl group. However, R ₄ is the general formula (), R ₁ is a lower alkoxy group or a lower haloalkoxy group,
is 1 and Z is a methine group, R ₅
represents only a methyl group. New 2- indicated by...
The present invention relates to an insecticide and acaricide characterized by containing a phenylpropyl ether derivative, and a method for producing the same. Conventionally, organic phosphorus agents or carbamate insecticides have been the mainstream pesticides and have contributed to improving agricultural production, but in recent years, resistance to these pesticides has significantly developed, and new types of insecticides are being developed due to their environmental pollution. There is a strong need for the creation of new agents. Recently, research has been widely conducted on plastid compounds that have modified the chemical structure of pyrethrin, a natural insecticidal ingredient. Because it is effective against sexual pests, it is expected to be an alternative to existing insecticides, and some are already being used for agricultural, household, and other uses.
It is widely used for epidemic prevention purposes. Until now, it has been considered difficult to develop resistance to these pyrethroids, and in fact, there have been very few cases in which it has become a problem in terms of control. It is considered appropriate to deal with it on the premise that there is a possibility of development. Therefore, the present inventors investigated the typical pyrethroid general formula that is currently widely used in practice.

We have started research to find an effective pyrethroid agent that can replace [Formula] in the event that resistance develops in the future. As a result of intensive research using pests that had been culled over many generations in the laboratory to reduce their susceptibility, a pyridine ring was introduced in place of the benzene ring, as in the compound represented by the general formula (). The inventors completed the present invention by discovering that nitrogen atom-substituted compounds exhibit high insecticidal power against resistant pests as well as susceptible pests, while having extremely low toxicity to warm-blooded animals and fish and shellfish. The compound represented by the above formula () used as an active ingredient in the present invention can be prepared using the general formula (In the formula, is an integer from 1 to 3, and R ₁ is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower haloalkyl group, a lower haloalkoxy group, a phenoxy group, an ethynyl group, a methylene Dioxy group, nitrile group or nitro group) or its reactive derivative and the general formula (In the formula, R ₂ represents a hydrogen atom, a cyano group, an ethynyl group, a methyl group, or a 1-propynyl group, R ₃ represents a hydrogen atom or a fluorine atom, and R ₄ represents the general formula (), (), () The group represented by is shown below. Here, A represents an oxygen atom or a methylene group.
Z is a nitrogen atom or a methine group, and X is a hydrogen atom, a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group, or an ethynyl group. R ₅ represents a hydrogen atom or a methyl group, and Y represents a hydrogen atom, a methyl group, a halogen atom, or a trifluoromethyl group. However, if R ₄ is the general formula (),
When R ₁ is a lower alkoxy group or a lower haloalkoxy group, is 1, and Z is a methine group, R ₅ represents only a methyl group. It is prepared by reacting the alcohol represented by or its reactive derivative. Examples of reactive derivatives of alcohol include chloride, bromide,
Examples include P-toluenesulfonic acid ester. The reaction is carried out in a suitable solvent in the presence of an optional deoxidizing agent or an organic or inorganic base or acid as a catalyst, optionally with heating. In the general formula (), except when R ₂ is a hydrogen atom, there is a non-sacrificial carbon, and what can be obtained by ordinary synthesis methods is a mixture of these, but each of these is of course included in the present invention. . Representative examples of the compound represented by the above formula () are shown below, but the present invention is of course not limited to these. 3'-(4-pyridyloxy)benzyl 2-methyl-2-(4-ethoxyphenyl)propyl ether n ²⁰ _D 1.5654 3'-(1,3-pyrimidine-2-oxy)-2'-cyanobewadyl, 2-methyl-2-(4-ethoxyphenyl)propyl ether n ²⁰ _D 1.5703 3'-(N-pyrrolylmethyl)benzyl 2-methyl-2-(4-chlorophenyl)propyl ether n ²⁰ _D 1.5517 3'(4-pyridylmethyl)-2'-ethynylbenzyl 2-methyl-2-(4-chlorophenyl)probyl ether n ²⁰ _D 1.5675 3'-(4-pyridyloxy)benzyl 2-methyl-2-(4-tert-butylphenyl)propyl ether n ²⁰ _D 1.5728 3'-(4-pyridylamino)-2'-(1-propynyl)benzyl 2-methyl-2-(2-chloro-
4-Trifluoromethylphenyl)propyl ether n ²⁰ _D 1.5833 3'(4-pyridyloxy)-4'-fluorobenzyl 2-methyl-2-(4-methylphenyl)propyl ether n ²⁰ _D 1.5621 3'-(4-pyridylmethyl)-2'-methylbenzyl 2-methyl-2-(4-ethylthiophenyl)
Propyl ether No ₂₀ 1.5686 3'-(1,3-pyrimidine-2-oxynobenzyl 2-methyl-2-(4-difluoromethoxyphenyl)propyl ether n ²⁰ _D 1.5640 3'-(N-pyrazoylmethyl)-2'-cyanobenzyl 2-methyl-2-(3,4-dichlorophenyl)propyl ether n ²⁰ _D 1.5661 3'-(4-fluoro-2-pyridyloxy)benzyl 2-methyl-2-(3,4-methylenedioxyphenyl)propyl ether n ²⁰ _D 1.5692 3'-(N-methyl-4-bromoanilino)-2'-ethynylbenzyl 2-methyl-2-(3-nitro-4-isopropylphenyl)propyl ether
n ²⁰ _D 1.5804 3'-(5-trifluoromethyl-3-pyridylmethyl)-2'-(1-propynyl)benzyl 2-methyl-2-(3-ethyl-4-bromophenyl)propyl ether No ₂₀ 1.5825 3'-(4-methoxy-2-pyridylamino)2-
Methylbenzyl 2-methyl-2-(2-fluoro-4-chloromethylphenyl)propyl ether n ²⁰ _D 1.5798 3'(3-ethynyl-4-pyridyloxy)-4'-fluoro-2'cyanobenzyl 2-methyl-2-(2,
6-dimethyl-4-ethynyl phenyl)propyl ether n ²⁰ _D 1.5739 3'-(1,3-pyrimidine-5-chloro-2-methyl)-2'-(1-propynyl)benzyl 2-methyl-2-(2-nitro-4-phenoxyphenyl)propyl ether n ²⁰ _D 1.6015 3'-(3-methyl-N-pyrrolylmethyl)2'-methylbendia 2-methyl-2-(3-cyano-
4-Methylthiophenyl)propyl ether
n ²⁰ _D 1.5570 3'(N-methyl-3-trifluoromethyl-2-
pyridylamino)-2'-cyanobenzyl 2-methyl-2-(2,5-difluoro-4-isopropylphenyl)propyl ether n ²⁰ _D 1.5863 3'-(5-bromo-2-pyridyloxy)-2'-methylbenzyl 2-methyl-2-(3,4-methylenedioxy-6-cyanophenyl)propyl ether n ²⁰ _D 1.5904 3'-(1,3-pyrimidine-2-methyl-4-oxy)-4'-fluoro-2'-ethynylbenzyl
2-Methyl-2-(3-methoxy-4-trifluorotylphenyl)propyl ether n ²⁰ _D 1.5842 3'-(4-fluoroanilino)benzyl 2-methyl-2-(2-chloro-4-trifluoromethoxyphenyl)propyl ether n ²⁰ _D 1.5739 3'-(4-trifluoromethyl-N-pyrazoylmethyl)-4'-fluoro-2'-(1-propynyl)
Benzyl 2-methyl-2-(3-nitro-4-
Ethynylphenyl) propyl ether n ²⁰ _D
1.5873 3'-(4-methoxy-2-pyridylmethyl)-4'-
Fluoro-2'-cyanobenzyl 2-methyl-2
-{3-methyl-4-(1-bromo-2-chloroethoxy)phenyl}propyl ether n ²⁰ _D
1.5968 3'-(N-methyl-3-ethynylanilino)-4'-
Fluoro-2'-methylbenzyl 2-methyl-2-
(3-phenoxyphenyl)propyl ether
n ²⁰ _D 1.6026 3'-(4-pyridylamino)-4'-fluorobenzyl 2-methyl-2-(4-chlorophenyl)propyl ether n ²⁰ _D 1.5705 3'-(1,3-pyrimidine-4-methoxy-2-
oxy)-4'-fluoro-2'-(1-propynyl)
Benzyl 2-methyl-2-(4-tertiary-
Butyl-6-fluorophenyl)propyl ether n ²⁰ _D 1.5963 3'-(2-fluoro-4-pyridylmethyl)benzyl 2-methyl-2-(4-methylphenyl)
Propyl ether n ²⁰ _D 1.5659 3'-(1,3-pyrimidine-6-ethynyl-4-
methyl)-4-fluoro-2'-cyanobenzyl
2-Methyl 2-(4-ethylthiophenyl)propyl ether n ²⁰ _D 1.5780 3'-(3-chloro-N-pyrrolylmethyl)-4'-fluorobenzyl 2-methyl-2-(4-trifluoromethylphenyl)propyl ether n ²⁰ _D
1.5613 3'-(3-Fluoro-N-pyrazoylmethyl)benzyl 2-methyl-2-(3,4-methylenedioxyphenyl)propyl ether n ²⁰ _D 1.5778 3'-(4-pyridylmethyl)-4'-fluorobenzyl 2-methyl-2-(4-ethoxyphenyl)
Propyl ether n ²⁰ _D 1.5671 3'-(N-methyl-4-chloroanilino)benzyl 2-methyl-2-(4-ethoxyphenyl)
Propyl ether n ²⁰ _D 1.5740 3'-(N-pyrazoylmethyl)-2'-methylbenzyl 2-methyl-2-(4-ethoxyphenyl)
Propyl ether n ²⁰ _D 1.5685 3'-(4-trifluoromethyl-2-pyridyloxy)-4'-fluorobenzyl 2-methyl-2-
(4-Ethoxyphenyl)propyl ether n ²⁰ _D
1.5708 3'-(4-Methyl-N-pyrazoylmethyl)benzyl 2-methyl-2-(3-chloro-4-methylphenyl)propyl ether n ²⁰ _D 1.5716 3'-(3-methyl-4-pyridyloxy)-2'-ethynylbenzyl 2-methyl-2-(3-methylthio-4-propylphenyl)propyl ether
n ²⁰ _D 1.5871 The compound used as an active ingredient in the insecticide and acaricide of the present invention is a new compound, is solid or liquid at room temperature, and is generally easily soluble in organic solvents. Therefore, as an insecticide for spraying, it can be used as an emulsion, oil, powder, wettable powder, aerosol, etc.
It can also be mixed with wood flour or other suitable base material and used as an insecticide for fumigation such as mosquito coils.
Also, when used as a so-called electric mosquito repellent, in which the active ingredient is dissolved in an appropriate organic solvent and soaked in a mount, or dissolved in an appropriate solvent and heated and evaporated with an appropriate heating element, it is as good as a mosquito coil. This shows the effect of The compound of the present invention is more stable to light than conventional pyrethroids, has a broader insecticidal spectrum, has low toxicity, and is inexpensive, so it can be used as an alternative to conventional organophosphorus agents and organochlorine insecticides. It can be used as an agricultural and horticultural insecticide. The insecticide and acaricide of the present invention can be used for flies,
In addition to sanitary pests such as mosquitoes and cockroaches, organophosphorus and carbamate resistant leafhoppers, planthoppers, stink bugs, stink bugs, armyworms, canker moths, tobacco moths, bean weevils, nocturnal moths, cabbage moths, chestnut beetles, leafhoppers, aphids, and scale insects. It is extremely useful for the control of agricultural pests such as, grain storage pests such as brown elephant, mites, etc.
In addition, N-octylbicycloheptine dicarboximide (trade name) is used as the insecticide and acaricide of the present invention.
MGK-264), a mixture of N-octylbicycloheptenedicarboximide and arylsulfonate (trade name MGK-5026), sinepirin 500, octachlorodipropyl ether, piperonyl butoxide, etc. are added. The insecticidal effect can be further enhanced. In addition to the insecticides and acaricides of the present invention, other insecticides such as organic phosphorus agents such as fenitrothion, DDVP, diazinon, propaphos, and pyridafentione, NAC,
Carbamate agents such as MTMC, BPMC, PHC,
Pyrethrin, allethrin, cotarthrin, flamethrin, phenothrin, permethrin, cypermethrin, decamethrin, fuenvalerate,
Conventional pyrethroid insecticides such as fenpropanate, insecticides such as cartap, chlorphenamidine, and methomyl, or acaricides, fungicides, nematicides, herbicides, plant growth regulators, fertilizers, and other agricultural chemicals. By mixing, a multi-purpose composition with excellent effects can be obtained, labor saving, and synergistic effects between the drugs can be fully expected. Next, examples of synthesizing compounds used as active ingredients in the present invention will be shown. The alcohol of general formula () is easily synthesized, for example, according to FIG. 1, as described in JP-A-55-148279. On the other hand, the alcohol represented by the general formula () is
It can be easily obtained by ordinary reduction reaction of 3-substituted benzoic acid. Synthesis Example 1 0.9 g of sodium hydride (60% in oil) was added to 20 ml of dry acetonitrile, and then a solution of 3.7 g of 2-methyl-2-(4-chlorophenyl)propyl alcohol dissolved in 10 ml of acetonitrile was added.
It was added dropwise at 50°C. After heating under reflux for 30 minutes, 3-
(N-pyrosolmethyl)benzyl bromide 5.1g
A solution prepared by dissolving this in 10 ml of acetonitrile was added dropwise over 10 minutes, and the mixture was further heated under reflux for 1 hour. After cooling to room temperature, water was added and extracted with toluene. The toluene extract was washed with saturated brine and dried over Glauber's salt. The crude ether obtained by distilling off toluene under reduced pressure was purified by column chromatography on 100 g of silica gel to obtain 3'-(N-pyrrolylmethyl).
6.0 g of benzyl, 2-methyl-2-(4-chlorophenyl)propyl ether was obtained. Synthesis Example 2 4.6 g of 2-methyl-2-(2,5-difluoro-4-isopropylphenyl)propyl alcohol and 2.3 g of potassium tertiary butoxide were dissolved in 100 ml of dry tertiary butanol, and then 3-tertiary butanol was dissolved. (N-methyl-3-trifluoromethyl-
6.5 g of 2-pyridylamino)-2-cyanobenzyl chloride was added, and the mixture was heated and stirred at about 80°C for 3 hours. After the reaction was completed, the reaction solution was allowed to cool, and the precipitated crystals were separated into three parts. The oil obtained by concentrating the three liquids was purified using a silica gel column to obtain 3'-(N-methyl-3-trifluoromethyl-2-pyridylamino)-2'-cyanobenzyl 2-methyl-2-( 2,
8.6 g of 5-difluoro-4-isopropylphenyl)propyl ether was obtained. Synthesis Example 3 15.0 g of 50% NaOH aqueous solution, 2-methyl-2-(3
-methoxy-4-trifluoroethyl phenyl)
Add 5.3 g of propyl alcohol, 5.3 g of 3-(1,3-pyrimidine-2-methyl-4-oxy)-4-fluoro-2-ethynylbenzyl chloride and 1 g of tetrabutylammonium bromide;
The mixture was heated and stirred at 80°C for 1 hour. After cooling to room temperature, water was added, extracted with benzene, and washed with water. After drying the benzene extract over Glauber's salt, the benzene was distilled off under reduced pressure, and the resulting crude ether was purified using a silica gel column to obtain 3'-(1,3-pyrimidine-2).
8.5 g of -methyl-4-oxy)-4'-fluoro-2'-ethynylbenzyl 2-methyl-2-(3-methoxy-4-trifluoroethyl phenyl)propyl ether were obtained. Synthesis Example 4 4.8 g of the sodium salt of 2-methyl-2-(3,4-methylenedioxy-6-cyanophenyl)propyl alcohol was dissolved in 50 ml of dimethylformamide, followed by 3-(5-bromo-2-pyridyl). Add 6.9 g of oxy)-2-benzyl bromide to 60
The mixture was stirred at ℃ for 4 hours. The reaction solution was diluted with 100 ml of water, extracted with ether, and the ether solution was thoroughly washed with dilute hydrochloric acid, aqueous sodium bicarbonate, and brine. The oil obtained by distilling off the ether under reduced pressure was purified using a silica gel column to give 3'-(5-bromo-2-pyridyloxy)-2'-methylbenzyl 2-methyl-
8.7 g of 2-(3,4-methylenedioxy-6-cyanophenyl)propyl ether was obtained. Synthesis Example 5 20 ml of toluene, 2 ml of concentrated sulfuric acid, 2-methyl-2-
(4-ethoxyphenyl)propyl alcohol
3.9 g and 4.3 g of 3-(4-pyridylmethyl)-4-fluorobenzyl alcohol were added, and the mixture was heated under reflux for 6 hours while removing the produced water from the system. After cooling to room temperature, add water, separate the toluene layer, wash with water,
Dry. The oil obtained by distilling toluene off under reduced pressure was purified using a silica gel column to obtain 3'-(4
-pyridylmethyl)-4'-fluorobenzyl2-
6.1 g of methyl-2-(4-ethoxyphenyl)propyl ether was obtained. Next, in order to make it clearer that the composition provided by the present invention is excellent, the results of the test results will be shown. Test Example 1 Insecticidal test by spraying 0.2% white light solution (A) of the compound of the present invention, 0.2%
and Cinepirin 500 0.8% White Light Solution (B), 0.1
% and phthalthrin 0.1% white lamp solution (C), and 0.2% white lamp solution of allethrin and phthalthrin, respectively. The mortality rate was calculated as follows. The numbers in parentheses indicate the mortality rate after 24 hours.

【table】

[Table] Test Example 2 Insecticidal test by fumigation Mosquito coils containing 0.5% of insecticidal ingredients were prepared and tested for their effectiveness in causing adult Culex mosquitoes to fall and roll over. This experiment was published in Insect Control Science Volume 16 [1951].
The relative effectiveness of the incense stick was calculated according to the method of Nagasawa, Katsuta et al., p. 176, and the results were as follows. The sample drug number is the same as that of the active ingredient example above.

[Table] Test Example 3 Insecticidal test using microdropping method Acetone solutions of each of the control compound and the compound of the present invention were added to the susceptibility and super
The compound was applied to the thoracic dorsal plate of adult -kdr house flies, and the relative insecticidal power to the control drug and the resistance ratio to the compound were determined from the mortality rate after 24 hours.The results are as follows.

[Table] Examples of formulations are shown next, but the formulations do not require any special conditions and can be prepared by methods familiar to those skilled in the art, similar to general agricultural chemicals. Reference example 1 White kerosene was added to 0.2 parts of the present compound (1) and the whole
Obtain 0.2% oil solution as 100 parts. Reference Example 2 White kerosene is added to 0.2 parts of the present compound (4) and 0.8 parts of piperonyl butoxide to make a total of 100 parts to obtain an oil agent. Reference Example 3 To 20 parts of the compound (6) of the present invention, 10 parts of Solpol SM-200 (registered trademark of Toho Chemical) and 70 parts of xylol were added and mixed and dissolved with stirring to obtain a 20% emulsion. Reference Example 4 0.4 parts of the compound of the present invention (11), 0.1 parts of resmethrin, and 1.5 parts of octachlorodipropyl ether are dissolved in 28 parts of refined kerosene, filled into an aerosol container, and after the valve part is attached, the propellant ( Fill 70 parts of liquefied petroleum gas under pressure to obtain an aerosol. Reference Example 5 0.5 g of the compound (17) of the present invention and 0.5 g of BHT were added to base materials for mosquito coils such as pyrethrum extract lees powder, wood flour, and starch powder.
Mix 99.0g uniformly and obtain a mosquito coil by a known method. Reference Example 6 0.4 g of the compound (22) of the present invention and 1.0 g of HGK-5026 are uniformly mixed with 98.6 g of a base material for a mosquito coil to obtain a mosquito coil by a known method. Reference Example 7 0.3 parts of the compound of the present invention (25) and 99.7 parts of clay are thoroughly ground and mixed to obtain a 0.3% powder. Reference Example 8 40 parts of the present compound (29), 35 parts of diatomaceous earth, clay
20 parts of lauryl sulfonate, 3 parts of lauryl sulfonate, and 2 parts of carboxymethyl cellulose are ground and mixed to obtain a wettable powder. Test Example 4 5 to 5 on a surface where a large number of green peach aphids appeared
Compounds of the present invention 11, 6, 10, 15, 18, 23, 27 among the emulsions obtained in Reference Example 3 in the radish field at the 6 drug stage
A 1000-fold diluted solution of each emulsion containing 1 and 35 with water was sprayed at 100 times per area. Two days later, the parasitism rate was investigated and found to have decreased to less than 1/10 of the spray agent density in each area. Test Example 5 Fresh leaves of Kanran were immersed in a 2000-fold diluted solution of compounds 2, 6, 9, 14, 20, 26, 30, and 37 of the present invention among the emulsions obtained in Reference Example 3 for about 5 seconds, After the chemical solution was dried, it was placed in a shear container and 10 healthy armyworm larvae were released. The test insects were released twice, once on the day of immersion in the crude drug, and 5 days later, and the mortality rate after 24 hours was determined.

[Table] Test Example 6 Approximately 200 aphids were infested on one tree one day before applying the insecticidal ingredient to potted fava beans. 4 of the hydrating agents obtained in Reference Example 8,
Spray 4000 times diluted solutions of 8, 13, 19, 22, 29, 33 and 36 onto infested leaves by compressed air spraying at 10 mm/min.
The degree of damage was observed two days after spraying on each pot.
As a result, no increase in the degree of damage was observed in any of the cases. Test Example 7 5, 7, 12, 16, obtained by Reference Example 7
Each of the powders Nos. 21, 25, 28 and 34 was uniformly sprinkled on the bottom of a tall glass shear dish with a diameter of 14 cm at a rate of 2 g/m ² , and the butter was applied to the wall leaving about 1 cm of the bottom. If you release a group of 10 adult German cockroaches into the container, leave them in contact for 30 minutes, and then transfer the cockroaches to a new container, after 3 days, no powder will be used.
It was able to kill more than 80% of cockroaches. Test Example 8 1 for 4 leaves of potted green beans 5 days after sowing
Infested with 10 female adult spider mites per leaf.
Store in a constant temperature room at 27℃. After 6 days, a chemical solution prepared by diluting emulsions 6, 11, 17, 24, 27, 31, and 36 obtained in Reference Example 3 with water to 100 ppm of active ingredients was sprayed on a turntable in 10 ml per pot, and after 10 days, it was sprayed on the plants. We investigated the number of parasitic spider mites in Japan. As a result, all of the insecticides and acaricides of the present invention were found to have acaricidal effects superior to the control agents.

[Table] Test Example 9 Carp was used as the subject, and the test was carried out in accordance with the toxicity test method for fishes, Notification No. 2735 of Agricultural Policy No. B (November 25, 1966), and the compounds of the present invention 1, 7, 11, 18,
When the TLm48ppm of 25, 29, 32 and 37 was determined, all of them were 0.8 or higher.

Claims (1)

[Claims] 1. General formula (In the formula, is an integer from 1 to 3, and R ₁ is
It represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower haloalkyl group, a lower haloalkoxy group, a phenoxy group, an ethynyl group, a methylenedioxy group, a nitrile group, or a nitro group. R ₂ represents a hydrogen atom, a cyano group, an ethynyl group, a methyl group, or a 1-propynyl group; R ₃ represents a hydrogen atom or a fluorine atom;
R ₄ represents a group represented by the general formula (), (), (). Here, A represents an oxygen atom or a methylene group. Z is a nitrogen atom or a methine group, and X is
Indicates a hydrogen atom, a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group, or an ethynyl group. R ₅ represents a hydrogen atom or a methyl group, and Y represents a hydrogen atom, a methyl group, a halogen atom, or a trifluoromethyl group. However, R ₄ is the general formula (), R ₁ is a lower alkoxy group or a lower haloalkoxy group,
is 1 and when Z is a methine group, R ₅ represents only a methyl group. ) An insecticide and acaricide characterized by containing a 2-phenylpropyl ether derivative represented by the following. 2 General formula (In the formula, is an integer from 1 to 3, and R ₁ is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower haloalkyl group, a lower haloalkoxy group, a phenoxy group, an ethynyl group, a methylene dioxy group, nitrile group, or nitro group) or its reactive derivative, and the general formula (In the formula, R ₂ represents a hydrogen atom, a cyano group, an ethynyl group, a methyl group, or a 1-propynyl group, R ₃ represents a hydrogen atom or a fluorine atom, and R ₄ represents the general formula (), (), Indicates a group represented by (). Here, A represents an oxygen atom or a methylene group. Z is a nitrogen atom or a methine group, and X is
Indicates a hydrogen atom, a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group, or an ethynyl group. R ₅ represents a hydrogen atom or a methyl group, and Y represents a hydrogen atom, a methyl group, a halogen atom, or a trifluoromethyl group. However, when R ₄ is the general formula (), R ₁ is a lower alkoxy group or a lower haloalkoxy group, and Z is a methine group, R ₅ represents only a methyl group. ) A general formula characterized by reacting with an alcohol or its reactive derivative represented by (Here, R ₁ , R ₂ , R ₃ , and R ₄ have the same meanings as above.) A method for producing an insecticide or acaricide containing a 2-phenylpropyl ether derivative.