JPH0261444B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a method for producing a 3-phenoxybenzyl 2-phenylpropyl ether derivative, and more specifically, the general formula () K0004 [In the formula (), R is a methyl group or an ethyl group,
R ¹ represents a hydrogen atom, a halogen atom or a lower alkyl group, R ² represents a halogen atom or a lower alkyl group, and X represents a halogen atom] and a 2-phenyl-2-alkylpropyl halide derivative represented by the general formula ( ) K0005 [In the formula (), M represents a hydrogen atom, an alkali metal atom, or an alkaline earth metal atom] A general formula characterized by reacting with 3-phenoxybenzyl alcohol or its metal alkoxide () K0006 This relates to a method for producing a 3-phenoxybenzyl 2-phenylpropyl ether derivative represented by the formula (), in which R, R ¹ and R ² each have the same meanings as above. Until now, pesticides have played an extremely important role in improving agricultural production, and the appearance of synthetic organic pesticides has completely changed the food situation for humankind, and has also brought great benefits in terms of epidemic prevention, such as preventing infectious diseases transmitted by insects. brought about. However, organochlorine insecticides DDT and BHC
Their use is limited because they remain in the environment for a long time after use, and organophosphorus insecticides and carbamate insecticides, which have replaced these insecticides, are widely used. Problems of resistance to these insecticides have arisen in several insect pests. In addition, difficult-to-control pests are appearing in some areas, and it is expected that problems such as drug-resistant pests will continue to spread and become more serious in the future. Today, in order to maintain an adequate supply of food, there is an urgent need for drugs with better insecticidal activity. In recent years, synthetic pyrethroid insecticides have been in the spotlight against this background. It has excellent insecticidal power and is highly effective against pests resistant to organophosphates or carbamates, and is characterized by relatively low toxicity to humans and livestock. However, the fatal drawback of this synthetic pyrethroid insecticide is that it is extremely toxic to fish, which limits its range of use. Furthermore, it is more expensive than conventionally developed insecticides. Agrochemicals that are desired in the future must be ones that solve the above-mentioned drawbacks. In other words, it is desirable to have a product that does not pollute the environment, has high activity against drug-resistant and difficult-to-control pests that are currently a problem, is highly safe for not only humans and livestock, but also fish, and is also inexpensive. It is required that it can be manufactured. The present inventors planned the development of an insecticide and acaricide that satisfies the above conditions, and as a result of diligent research, we found that 3-phenoxybenzyl 2-
Phenylpropyl ether derivatives have extremely high insecticidal and acaricidal activity, and have excellent characteristics in terms of immediate effect and residual effect, and are of course effective against humans and livestock.
It was also found that toxicity to fish is low. Therefore, the present inventors have determined that 3 expressed by the general formula ()
-As a result of further studies on the production method of phenoxybenzyl 2-phenylpropyl ether derivatives, we found that 2-phenyl-2-alkylpropyl halide derivatives represented by the general formula () and 3-phenoxyl halide derivatives represented by the general formula () When cybenzyl alcohol or its metal alkoxide is reacted, especially when a halide of the general formula () and 3-phenoxybenzyl alcohol are reacted in the presence of an aprotic polar solvent, preferably dimethyl sulfoxide or sulfolane, the general formula The present invention was completed by discovering that the 3-phenoxybenzyl 2-phenylpropyl ether derivative represented by () can be obtained in good yield. The 3-phenoxybenzyl 2-phenylpropyl ether derivative produced by the method of the present invention has the general formula () K0007 [In the formula (), R represents a methyl group or an ethyl group, and R ¹ is a hydrogen atom or a halogen atom. R2 represents a halogen atom or a lower alkyl group, and ^R2 represents a halogen atom or a lower alkyl group, respectively]. Specifically, ^R1 and ^R2 represent a hydrogen atom ( ^R1
), fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group,
i-propyl group, n-butyl group, S-butyl group,
Examples include i-butyl group and t-butyl group. Next, typical examples of 3-phenoxybenzyl 2-phenylpropyl ether derivatives produced by the method of the present invention will be shown, but the invention is not limited to these exemplified compounds. Note that the 3-phenoxybenzyl 2-phenylpropyl ether derivative produced by the method of the present invention has an asymmetric carbon when R is an ethyl group, and optical isomers exist. Also included. 3-Phenoxybenzyl 2-(4-methylphenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4-promophenyl)-2-
Ethylpropyl ether, 3-phenoxybenzyl 2-(3-chloro-4-methylphenyl)-2methylpropyl ether, 3-phenoxybenzyl 2-(3,4-dibromophenyl)-2-methylpropyl ether , 3-phenoxybenzyl 2-
(4-chlorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(4-t-butylphenyl)-2-methylpropyl ether,
3-Phenoxybenzyl 2-(4-fluorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3-bromo-4-chlorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3-bromo-4-chlorophenyl)-2-ethylpropyl ether Cybenzyl 2-(3,4-dichlorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4-bromophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4 -ethyl phenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4-fluorophenyl)-2-ethylpropyl ether,
3-Phenoxybenzyl 2-(3-chloro-4-
Fluorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(4-ethylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3,4-dichlorophenyl)-2 -ethylpropyl ether, 3-phenoxybenzyl 2-(4-chloro-3-methylphenyl)-2-methylpropyl ether, 3-phenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4 -t-butylphenyl)-
2-Ethylpropyl ether, 3-phenoxybenzyl 2-(3,4-dimethylphenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3-chloro-4-methylphenyl)-2- Ethylpropyl ether, 3-phenoxybenzyl 2-(3-bromo-4-chlorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3,4-dibromophenyl)-2-ethylpropyl Ether, 3-phenoxybenzyl 2-
(4-chloro-3-methylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-
(4-iodophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4-chlorophenyl)-2-methylpropyl ether, 3-
Phenoxybenzyl 2-(3,5-dichlorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3,4-dimethylphenyl)
-2-ethylpropyl ether, 3-phenoxybenzyl 2-(4-methylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-
(3-chloro-4-fluorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2
-(3,4-difluorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-
(3,4-difluorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(6
-bromo-4-fluorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-
(3-bromo-4-fluorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2
-(3-fluoro-4bromophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2
-(3-fluoro-4-bromophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(4-bromo-3-chloro-phenyl)-2-
Methylpropyl ether, 3-phenoxybenzyl 2-(4-bromo-3-chloro-phenyl)-2
-Ethylpropyl ether, 3-phenoxybenzyl 2-(4-fluoro-3-methylphenyl)-
2-Methylpropyl ether, 3-phenoxybenzyl 2-(4-fluoro-3-methylphenyl-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3-fluoro-4-methylphenyl)-2-methyl Propyl ether, 3-phenoxybenzyl 2-(3-fluoro-4-methylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3-bromo-4-methylphenyl)-2-methylpropyl ether , 3-
Phenoxybenzyl 2-(3-bromo-4-methylphenyl)-2-ethylpropyl ether, 3
-Phenoxybenzyl 2-(3,4-diethyl-
phenyl)-2-methylpropyl ether, 3-
Phenoxybenzyl 2-(3,4-diethyl-phenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(4-i-propylphenyl)-2-methylpropyl ether, 3-phenoxylphenyl Sibenzyl 2-(4-i-propylphenyl)-
2-ethylpropyl ether, 3-phenoxybenzyl 2-(3,4-di-i-propylphenyl)
-2-Methylpropyl ether, 3-phenoxybenzyl 2-(3,4-di-i-propylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3,4-di- t-butylphenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3,4-di-t-butylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3-ethyl- 4-methylphenyl)-2-methylpropyl ether, 3-
Phenoxybenzyl 2-(3-ethyl-4-methylphenyl)-2-ethylpropyl ether, 3
-phenoxybenzyl 2-(4-ethyl-3-methylphenyl)-2-methylpropyl ether,
3-Phenoxybenzyl 2-(4-ethyl-3-
methylphenyl)-2-ethylpropyl ether,
3-Phenoxybenzyl 2-(4-t-butyl-
3-Methylphenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4-t-butyl-3-methylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(4-
i-propyl-3-methylphenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2
-(4-i-propyl-3-methylphenyl)-2
-ethylpropyl ether, etc. 2- used as a raw material in the method of the present invention
The phenyl-2-alkylpropyl halide derivative is represented by the general formula () K0008 [In the formula (), R, R ¹ , R ² and X each have the same meaning as above], specifically 3
-Chloroneophyl chloride, 3-chloroneophyl bromide, 1-chloro-2-(3-chlorophenyl)-2-methylbutane, 1-bromo-2-
(3-chlorophenyl)-2-methylbutane, 4-
Chloroneophyl chloride, 4-chloroneophyl bromide, 1-chloro-2-(4-chlorophenyl)-2-methylbutane, 1-bromo-2-(4
-chlorophenyl)-2-methylbutane, 3-bromoneofyl chloride, 3-bromoneofyl bromide, 1-chloro-2(3-bromophenyl)
-2-Methylbutane, 1-bromo-2-(3-bromophenyl)-2-methylbutane, 4-bromoneofyl chloride, 4-bromoneofyl bromide, 1-chloro-2-(4-bromophenyl)-
2-Methylbutane, 1-bromo-2-(4-bromophenyl)-2-methylbutane, 3-iodoneophyl chloride, 3-iodoneophyl bromide, 1-chloro-2-(3-iodophenyl)-2
-Methylbutane, 1-bromo-2-(3-iodophenyl)-2-methylbutane, 4-iodoneophyl chloride, 4-iodoneophyl bromide, 1-chloro-2-(4-iodophenyl)-2
-Methylbutane, 1-bromo-2-(4-iodophenyl)-2-methylbutane, 3-fluoroneofyl chloride, 3-fluoroneofyl bromide, 1-chloro-2-(3-fluorophenyl)
-2-Methylbutane, 1-bromo-2-(3-fluorophenyl)-2-methylbutane, 4-fluoroneofyl chloride, 4-fluoroneofyl chloride, 1-chloro-2-(4-fluorophenyl) -2-methylbutane, 1-bromo-2-
(4-fluorophenyl)-2-methylbutane,
3,4-dichloroneophyl chloride, 3,4-
Dichloroneophyl bromide, 1-chloro-2-
(3,4-dichlorophenyl)-2-methylbutane, 1-bromo-2-(3,4-dichlorophenyl)-2-methylbutane, 3,5-dichloroneofyl chloride, 3,5-dichloroneofyl Bromide, 1-chloro-2-(3,5-dichlorophenyl)-2-methylbutane, 1-bromo-2-
(3,5-dichlorophenyl)-2-methylbutane, 3-chloro-4-fluoroneofyl chloride, 3-chloro-4-fluoroneofyl chloride, 1-chloro-2-(3-chloro-4-fluoro phenyl)-2-methylbutane, 1-bromo-
2-(3-chloro-4-fluorophenyl)-2-
Methyl butane, 3-methylneofyl chloride,
3-Methylneophyl bromide, 1-chloro-2
-(3-methylphenyl)-2-methylbutane, 1
-Bromo-2-(3-methylphenyl)-2-methylbutane, 4-methylneofyl chloride, 4-
Methylneophyl bromide, 1-chloro-2-
(4-methylphenyl)-2-methylbutane, 1-
Bromo-2-(4-methylphenyl)-2-methylbutane, 3,4-dimethylneofyl chloride,
3,4-dimethylneophyl bromide, 1-chloro-2-(3,4-dimethylphenyl)-2-methylbutane, 1-bromo-2-(3,4-dimethylphenyl)-2-methylbutane, 4 -i-propylneofyl chloride, 4-i-propylneofyl bromide, 1-chloro-2-(4-i-propylphenyl)-2-methylbutane, 4-t-butylneofyl chloride, 1-chloro- 2-(4
-t-butylphenyl)-2-methylbutane, 3
-Chloro-4-methylneofyl chloride, 1-
Chloro-2-(3-chloro-4-methylphenyl)
-2-Methylbutane, 3,4-dibromoneophyl chloride, 3,4-dibromoneophyl bromide, 1-chloro-2-(3,4-dibromophenyl)-2-methylbutane, 1-bromo-2-( 3,
4-dibromophenyl)-2-methylbutane, 3
-Bromo-4-chloro-neofyl chloride, 1
-Chloro-2-(3-bromo-4-chlorophenyl)-2-methylbutane, 4-ethylneofyl chloride, 1-chloro-2-(4-ethylphenyl)-2-methylbutane, 3,4-difluoroneophyl chloride , 1-chloro-2-(3,
4-difluorophenyl)-2-methylbutane,
3-bromo-4-fluoroneofyl chloride,
1-chloro-2-(3-bromo-4-fluorophenyl)-2-methylbutane, 3-fluoro-4
-Methyl neophyl chloride, 1-chloro-2-
(3-fluoro-4-methylphenyl)-2-methylbutane, 3-bromo-4-methylneofyl chloride, 1-chloro-2-(3-bromo-4-methylphenyl)-2-methylbutane, 3,4-diethyl Neofil chloride, 1-chloro-2-
(3,4-diethylphenyl)-2-methylbutane, 3,4-di-i-propylneofyl chloride, 1-chloro-2-(3,4-diethylphenyl)-2-methylbutane, 3,4 -di-butylneofyl chloride, 1-chloro-2-(3,4-
diethylphenyl)-2-methylbutane, 4-ethyl-3-methylneofyl chloride, 1-chloro-2-(4-ethyl-3-methylphenyl)-2
-Methylbutane, 4-t-butyl-3-methylneofyl chloride, 1-chloro-2-(4-t-
butyl-3-methylphenyl)-2-methylbutane, 4-t-butyl-3-methylneofyl chloride, 1-bromo-2-(4-t-butyl-3-
methylphenyl)-2-methylbutane, 4-i-
Propyl-3-methylneofyl chloride, 4-
i-propyl-3-methylluneophyl bromide, 1-chloro-2-(4-i-propyl-3-
Examples include methylphenyl)-22-methylbutane, 1-bromo-2-(4-i-propyl-3-methylphenyl)-2-methylbutane, and the like. These 2-phenyl-2-alkyl-propyl halide derivatives are obtained by the reaction of benzene derivatives with 2-alkyl-allyl halides (Neftekhimiya, 2,776 (1962); Dutch Application No. 6601685). ; Chemical Berichte (Chem.Ber.94, 2609 (1961), Method for halogenating t-butylbenzene with sulfuryl halide [Chem.Ber.94, 2599]
(1961), etc. According to the method of the present invention, a 2-phenyl-2-alkylpropyl halide derivative of the general formula () and a 3-phenoxybenzyl alcohol of the general formula () or The desired 2-phenylpropyl ether derivative can be obtained by reacting the alkoxide in an appropriate solvent in the presence of a base as a deoxidizing agent at room temperature or with heating. In the method of the present invention, 2-phenyl-2- The ratio of the alkylpropyl halide derivative and 3-phenoxybenzyl alcohol or its alkoxide is 0.2 of the 2-phenyl-2-alkylpropyl halide derivative per mole of 3-phenoxybenzyl alcohol or its alkoxide.
A molar ratio of ~5 to 5, preferably 0.5 to 2, is appropriate; if the ratio used is outside this range, the reaction will be slow or more by-products will be produced, resulting in a lower yield. The base used in the method of the present invention is
Specifically, sodium hydroxide, potassium hydroxide,
Alkali metal hydroxides such as lithium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide, alkali metal hydrides such as sodium hydride, sodium methylate, potassium ethylate, potassium t-butoxy, etc. Examples include alkali metal alcoholates, alkali metal oxides such as sodium oxide, alkali metal carbonates such as potassium carbonate and sodium carbonate, sodium amide, triethylamine, pyridine, etc., and the amount used is 3-phenoxybenzyl alcohol or its derivatives. A suitable amount is 0.5-3 mol, preferably 1-2 mol. If the amount used is larger than this, the reaction rate will be low, and if it is larger than this, the production of by-products will increase and the yield will decrease. Solvents used in the method of the present invention include water, aromatic hydrocarbons such as benzene, toluene, and xylene, aliphatic hydrocarbons such as hexane, heptane, and petroleum benzene, halogenated hydrocarbons such as chloroform and dichloromethane, and dimethyl sulfoxide. , sulfolane, N-methyl-2-pyrrolidone,
Aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, hexamethylphosphoramide, ethers such as diisopropyl ether, diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, dioxane, acetonitrile, Nitriles such as propionitrile, ketones such as acetone and diisopropyl ketone can be used. The desired 2-phenylpropyl ether derivative can also be suitably obtained by using a phase transfer catalyst represented by tetra-2-butylammonium bromide, triethylbenzylammonium bromide, etc. as a catalyst. When using a solvent other than dimethyl sulfoxide, the reaction is promoted by allowing a small amount of dimethyl sulfoxide to coexist. It is also suitable to add catalytic amounts of potassium iodide, copper iodide, and the like. Preferred solvents are aprotic polar solvents, particularly dimethyl sulfoxide and sulfolane. The appropriate amount of the solvent to be used is 0.5 to 50 parts, preferably 2 to 20 parts, per part of 3-phenoxybenzyl alcohol or its alkoxide. If the amount used is less than this, the reaction will be very slow, and if it is more than this, the reaction will be slow and productivity will be low. A general embodiment of the invention is as follows.
A 2-phenyl-2-alkyl-propyl halide derivative, 3-phenoxybenzyl alcohol or alkoxide, a base, and a solvent are placed in a reaction vessel, and the temperature is between 50°C and the boiling point, preferably between 80°C and the boiling point (however, the boiling point is below 20°C). If it exceeds 80-200℃)
Heat at the same temperature for 0.5 to 50 hours, preferably 3 to 50 hours.
Stir for 30 hours. After cooling to room temperature, the insoluble inorganic salts are separated off. The solvent is removed from the solution by vacuum distillation, and the residue is washed with water and dehydrated to obtain the desired pendyl propyl ether derivative. This product has a high purity and can be used as an insecticide/acaricide as it is, but in some cases it can be further purified by vacuum distillation or column chromatography. This reaction is carried out in a normal air atmosphere, but if the reaction is carried out after purging the system with an inert gas such as nitrogen, the production of by-products may be suppressed and the yield may be improved. Furthermore, the order of addition of the 2-phenyl-2-alkylpropyl halide derivative, 3-phenoxybenzyl alcohol or alkoxide, and the base may be arbitrary, and in some cases, they may be charged in parts instead of all at once. It is possible. Next, the details of the manufacturing method of the present invention will be explained with reference to Examples. Example 1 8.53 g of p-chloroneofyl chloride, 8.0 g of m-phenoxybenzyl alcohol, 5.65 g of 45% caustic soda, and 48 g of dimethyl sulfoxide were placed in a reaction vessel, heated to 140°C, and stirred at the same temperature for 7 hours. Thereafter, it was cooled to room temperature and poured into 300 ml of water. Extraction was carried out three times with 100 ml of benzene, and the benzene layer was washed twice with 100 ml of saturated brine, and then dried over anhydrous sodium sulfate. 17.7 g of the crude product obtained by distilling off the solvent was purified by column chromatography using 250 g of silica gel (developing solvent: toluene-n-hexane 1:1) to obtain 3-phenoxybenzyl 2-(4-chlorophenyl). 6.91 g of )-2-methylpropyl ether (Compound No. 1) was obtained. The yield was 44.8% based on the p-chloroneofyl chloride used, and the consumed p-
Yield based on chloroneofyl chloride is 76.6%
It was hot. n ¹⁷ _D 1.5832 ν ^film _nax (cm ^-1 ) 1600, 1505, 1270, 1230, 1120,
1025, 840, 705 δ ^CCl4 (ppm); 1.26 (S, 6H), 3.25 (S, 2H),
4.27 (S, 2H), 6.6~7.3 (m,
13H) Elemental analysis results C ₂₃ H ₂₃ ClO ₂ Calculated value (%) C 75.30 H 6.32 Cl 9.66 Actual value (%) C 75.18 H 6.51 Cl 9.70 Example 2 p-chloroneofyl chloride 8.0 g, m-phenoxy Put 8.0 g of benzyl alcohol, 3.2 g of 50% caustic soda and 48 g of sulfolane into a reactor,
After heating to 130℃ and stirring at the same temperature for 3 hours,
It was treated in the same manner as in Example 1. 3-phenoxybenzyl 2-(4-chlorophenyl)-2-methylpropyl ether (compound number 1) 1.6 g (selectivity 85
%) was obtained. Example 3 25.5 g of p-isopropyl neophyl bromide,
m-Phenoxybenzyl alcohol 20.0g, 50%
14.5 g of caustic potash and 100 g of dimethyl sulfoxide
g was placed in a reactor and heated to 130°C, stirred at the same temperature for 8 hours, then cooled to room temperature. Add the reaction solution to 400ml of water.
and extracted three times with 100 ml of benzene.
The benzene layer was washed with water and then dried over anhydrous sodium sulfate. The crude product obtained by distilling off the solvent was purified by column chromatography to obtain 22.1 g of 3-phenoxybenzyl 2-(4-i-propylphenyl)-2-methylpropyl ether (compound number 2). I got it. (Yield 59%, yield 81% based on consumed p-chloroneofyl chloride). n ^20.2 _D 1.5683 Elemental analysis result as C ₂₆ H ₃₀ O ₂
Calculated value (%) C83.38 H8.07 Actual value (%) C83.19 H7.89 Next, other 3-phenoxybenzylpropyl ether derivatives represented by the general formula () synthesized in this way and their The physical properties of are shown in Table 1 below.

【table】

[Table] General formula () produced by the method of the present invention
3-phenoxybenzyl 2- represented by
Phenylpropyl ether derivatives are effective against sanitary pests such as flies, mosquitoes, and cockroaches, as well as agricultural pests such as planthoppers, leafhoppers, armyworms, diamondback moths, leafhoppers, aphids, caterpillars, and spider mites, especially leafhoppers. It is also effective against grain storage pests such as white mites, corn weevils, and weevils, animal-parasitic louse mites, house pests such as termites, and other pests. Representative test examples are shown below to demonstrate their efficacy. Test Example 1 Sweet potato leaves were immersed for 10 seconds in a chemical solution prepared by dissolving 1 part of each test compound (the same applies hereafter in "parts by weight") in 10 parts of acetone and adjusting the concentration to 100 and 20 ppm with water. The second instar larvae of Spodoptera were released into a cup and left in a constant temperature room at 25°C. 24 hours after the treatment, the number of living and dead insects was investigated, and the mortality rate was calculated. The results are shown in Table 2 as the average value of three consecutive tests. The test compounds are shown by the compound numbers in Example 1 and Table 1 above. (same as below)

[Table] Test Example 2 Young paddy rice seedlings (2 to 3 true leaves) were grown hydroponically in pots with a diameter of 5 cm, and 100 and 20 ppm concentrated drug solutions of each test chemical prepared in the same manner as Test Example 1 were added. 3 ml/pot of each was treated using a sprayer. After air-drying, the seedlings were covered with a wire mesh cylinder, and resistant leafhoppers (from Nakagawa) and susceptible leafhoppers (from Chigasaki) were isolated.
Ten female adults were released into each pot and placed in a glass greenhouse. 24 hours after treatment, the number of live and dead insects was investigated, and the mortality rate was calculated. The results are shown in Table 3 as three consecutive average values.

[Table] Comparative compounds are listed in Japanese Patent Publication No. 1983-
The following compounds described in Publication No. 106831 were used. K0009

Claims (1)

[Claims] 1 General formula () K0001 [In formula (), R is a methyl group or an ethyl group,
R ¹ represents a hydrogen atom, a halogen atom or a lower alkyl group, R ² represents a halogen atom or a lower alkyl group, and X represents a halogen atom], and a 2-phenyl-2-alkylpropyl halide derivative represented by the general formula () K0002 [In the formula (), M represents a hydrogen atom, an alkali metal atom or an alkaline earth metal atom] A general product characterized by reacting with 3-phenoxybenzyl alcohol or its metal alkoxide A method for producing a 3-phenoxybenzyl 2-phenylpropyl ether derivative represented by the formula () K0003 [in the formula (), R, R ¹ and R ² each have the same meanings as above].