WO2018120881A1 - Insecticidal ether compound having structure similar to pyrethroid - Google Patents

Abstract

The present invention provides an insecticidal ether compound having a structure similar to pyrethroid. The structural formula of the compound is represented by formula A, wherein R₁ and R₂ are methyl, a halogen atom, or trifluoromethyl, R₃ and R₄ are a H atom, methyl, or ethyl, and R₅ is a H atom, methyl, or methoxymethyl. Compared to a conventional pyrethroid insecticide, the compound of the present invention is less toxic to aquatic organisms, and has a better insecticidal effect on a certain target pest.

Description

An ether insecticidal compound having a pyrethroid-like structure Technical field

The invention relates to an insecticide, which is a kind of ether insecticidal compound having a pyrethroid-like structure, a preparation method thereof and application of pest control.

Background technique

Pyrethroid compounds are a class of biomimetic synthetic insecticides that can be used in a variety of pests and have high insecticidal activity. Pyrethroid compounds have high efficiency, low toxicity to mammals, low residue and good environmental compatibility, and have been widely used in the field of pest control. However, pyrethroid insecticides with an ester bond structure are highly toxic to aquatic fish and arthropods. For example, the acute toxicity of cypermethrin to zebrafish 96hLC50 is less than 0.1a.i.mg/L, which is highly toxic.

In the last century, Mitsui Chemical Co., Ltd. of Japan developed the Ethofenprox, which is different from the traditional pyrethroid. There is no ester bond in this compound, and the ether bond is replaced by it. This structural change reduces the toxicity to fish and achieves moderate to high toxicity, which can be used to control some rice field pests such as rice planthoppers. However, its efficacy is unsatisfactory relative to the ester-containing pyrethroids such as cyhalothrin and cypermethrin.

The inventors of the present invention have improved the preparation of a class of tetrafluorophenyl structures disclosed in the patents of US 4,370,346 A and the like by the long-term study of pyrethroid insecticides. Pyrethroids have proposed a new class of ether-containing insecticidal compounds, which are toxic to aquatic organisms such as zebrafish, which are in the range of moderate to high toxicity, and are superior to target pests such as rice planthopper. The effect of fenthrin. In addition, these compounds also have good control effects against mosquitoes, flies, cockroaches and other health pests.

Summary of the invention

One of the objects of the present invention is to provide an ether insecticidal compound having a pyrethroid-like structure which is useful for insecticidal purposes.

Another object of the present invention is to provide a process for the preparation of the above compounds.

A third object of the present invention is to provide the use of said compound as an active ingredient of a pesticide.

In order to achieve the above object, the present invention adopts the following technical solutions:

An ether insecticidal compound having a pyrethroid-like structure, the structure of which is as shown in Formula A:

Wherein R ₁ and R ₂ are a methyl group, a halogen atom or a trifluoromethyl group; R ₃ and R ₄ are a H atom, a methyl group or an ethyl group; and R ₅ is a H atom, a methyl group or a methoxymethyl group.

In the above technical solution, the R ₁ and R ₂ are a chlorine atom, R ₃ is a H atom, R ₄ is a methyl group, and when R ₅ is a methoxymethyl group, the compound has the following formula:

In the above aspect, the R ₁ and R ₂ are fluorine atoms, R ₃ and R ₄ are H atoms, and when R ₅ is H, the compound has the following structure.

In the above technical solution, the R ₁ is a chlorine atom, R ₂ is a trifluoromethyl group R ₃ , and R ₄ is a methyl group. When R ₅ is a methyl group, the compound has the following structure.

The present invention also provides a method for preparing an ether insecticidal compound having a pyrethroid-like structure represented by Formula A: using an alcohol represented by Formula B and a tetrafluorobenzene halogenated product represented by Formula C as a raw material, It is dissolved in an inert solvent such as DMF in the presence of NaH, and is subjected to an etherification synthesis reaction at room temperature to prepare the ether-like insecticidal compound having a pyrethroid-like structure;

The molar ratio of the alcohol to the tetrafluorobenzene halide is 1:1;

The alcohol is

The tetrafluorobenzene halogenated product is

The alcohol may be prepared by reduction of the corresponding chrysanthemic acid, or by gemalic acid chloride by Grignard reaction; the tetrafluorobenzene halogenated product is an existing compound.

In the present invention, each substituent in the formula is as defined above, and X is a halogen selected from fluorine, chlorine or bromine.

Since the compound of the formula A of the present invention has a double bond and a three-membered ring in the structure, and the groups to which they are attached are not completely identical, the corresponding ZE and cis and optical isomers are present, and the compounds of the present invention contain these specific stereoscopic forms. A single isomer of the structure or a mixture thereof.

The compounds of the formula A of the present invention prepared by the above methods are listed in Table 1.

Table 1

Note: The / in the configuration indicates that there is no such configuration, and the blank is an indistinguishable mixture.

The present invention also provides an application of an ether-like insecticidal compound having a pyrethroid-like structure represented by Formula A for controlling sanitary pests or agricultural pests.

In the above technical solution, the sanitary pest is a mosquito, a fly, a locust or a cockroach.

In the above technical solution, the agricultural pest is rice planthopper or the like.

In the above technical solution, the ether insecticidal compound is prepared as an active ingredient into a conventional preparation for controlling a sanitary pest or an agricultural pest;

When the ether-based insecticidal compound is prepared as an active ingredient into a conventional preparation, the conventional preparation includes the ether-based insecticidal compound itself, or includes the ether-based insecticidal compound and an inert carrier;

When the conventional preparation comprises the ether insecticidal compound and an inert carrier, the weight of the ether insecticidal compound is 0.001 to 95% by weight based on the total weight of the conventional preparation;

The conventional preparation can be prepared by the following method:

1 mixing the ether insecticidal compound of the present invention with a liquid and/or gaseous carrier, and optionally adding a surfactant for formulation and other adjuvants;

2 mixing the ether insecticidal compound of the present invention with a powdery solid carrier, and optionally adding a surfactant and other adjuvants for formulation; or

3 impregnating the shaped solid carrier with the ether-based insecticidal compound of the present invention; or mixing the compound of the present invention with a powdery solid carrier, and optionally adding a surfactant for formulation and other adjuvants, and shaping the resulting mixture.

In the above technical solution, the ether insecticidal compound is used as an insecticide active ingredient for controlling pests, and the ether insecticidal compound can be combined with pyrethroid, propythrin, methrin, and high-efficiency chlorine. Other insecticides such as cypermethrin, chlorpyrifos, avermectin, thiamethoxam, chlorantraniliprole, flubendiamide, etc. are used as an insecticidal active ingredient. It can be prepared into mosquito-repellent incense, electric liquid mosquito coil, electric mosquito-repellent incense film, aerosol or resin hanging piece suitable for volatilization at room temperature, filter paper ribbon, fan mosquito coil and other sanitary insecticide products.

Compared to conventional pyrethroid insecticides, the compounds of the invention are less toxic to aquatic organisms and have a better insecticidal effect on certain target pests.

detailed description

The technical solutions and effects of the present invention are explained in detail below by way of examples, but the present invention is not limited to the following examples. The following % content refers to the mass fraction unless otherwise specified.

Example 1: Compound 9 trans-1-(1-[3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropyl]-ethoxymethyl in Table 1 Synthesis of -2,3,5,6-tetrafluoro-4-methoxymethyl-benzene

1) Synthesis of methyl magnesium chloride:

In a 500 ml four-necked flask equipped with a stirring, a thermometer, and a condenser, 360 g of anhydrous tetrahydrofuran, 18 g of magnesium turnings, and one iodine were added, and the mixture was heated to 60 ° C, and the color of the iodine was removed. At this temperature, the methyl chloride to magnesium turning reaction is completed, the methyl chloride is stopped, the temperature is lowered, and the reaction liquid is ready for use. (The reactants in this step can also be replaced by commercially available methylmagnesium bromide)

2) Synthesis of trans-1-[3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropyl]-ethyl ketone:

Into a 1000 ml four-necked flask, 170.6 g of trans-3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropanoyl chloride was added, and anhydrous tetrahydrofuran was added, and the mixture was cooled to 10 °C. At this temperature, 225 g of the above solution was slowly added dropwise (0.75 mol of magnesium was converted). After the dropwise addition, the temperature was kept at this temperature for 8 hours. After the reaction was completed, 200 mL of water was added and stirred, and the aqueous layer was separated, and the aqueous layer was extracted with 3*200 mL of ethyl acetate. The organic phase was washed with water until neutral, and desolvated under reduced pressure to give 150 g crude. Column chromatography gave 65 g of 1-[3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropyl]-ethanone as a colorless oil.

3) Synthesis of trans-1-[3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropyl]-ethanol:

Into a 250 ml four-necked flask was placed 26 g of ethyl ketone prepared in the previous step, 52 g of methanol. At 25 ° C, 9.5 g of sodium borohydride was added in portions, and the reaction was carried out for one hour. The pH was adjusted to 5-6 with 15% hydrochloric acid, methanol was removed under reduced pressure, 200 g of water was added, and the mixture was extracted with 3*50 mL of chloroform. The organic phase was combined, washed with water until neutral, and then the oily liquid was dissolved in 24 g, yield 93%.

4) 1-Chloromethyl-2,3,5,6-tetrafluoro-4-methoxymethyl-benzene

In a 1000 ml four-necked flask with stirring, 104 g of (2,3,5,6-tetrafluoro-4-methoxymethyl-phenyl)-methanol, 400 g of dichloroethane, catalytic amount of DMF, at room temperature were added. 82.4 g of thionyl chloride was added dropwise. After completion of the dropwise addition, the mixture was refluxed for two hours, and dehydrated under reduced pressure to give 108 g of desired product.

5) trans-1-(1-[3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropyl]-ethoxymethyl)-2,3,5 ,6-tetrafluoro-4-methoxy Synthesis of methyl-benzene (ie, compound 9 of the present invention)

20 g of anhydrous DMF was added to a 250 mL four-necked flask, and 1.5 g of NaH was added under a nitrogen atmosphere. 5 g of trans-1-[3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropyl]-ethanol was dissolved in 10 g of DMF and then added dropwise to NaH containing at 20 °C. In the DMF solution, the mixture was stirred for 1 hour. 6 g of 1-chloromethyl-2,3,5,6-tetrafluoro-4-methoxymethyl-benzene was dissolved in 30 g of DMF, and added dropwise to the above solution at 5 °C. After the dropwise addition, the mixture was heated to room temperature and stirred for 4 hours. The reaction mixture was quenched by the addition of 200 g of water, and the aqueous phase was extracted with 3*50 mL of ethyl acetate. The organic phase was combined and washed with water to neutral. After lysing column chromatography, 6.5 g of pale brown oil was obtained. The yield was 66% and the content was 97.2%.

This compound is the compound of the invention 9: 1-(1-[3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropyl]-ethoxymethyl)- 2,3,5,6-tetrafluoro-4-methoxymethyl-benzene Molecular formula: C ₁₈ H ₂₀ O ₂ F ₄ Cl ₂ , molecular weight 415.25, mass spectrometer molecular ion peak M=414. 500 M nuclear magnetic resonance spectrum (1H (ppm) CDCl3): 5.63 (d, 1H); 3.01 (t, 1H); 0.87 (t, 1H); 0.51 (t, 1H); 4.67 (S, 2H); 4.63 (S, 2H); 3.24(s,3H);1.21(d,3H);1.11(s,6H).

Example 2: Table compound 10 1-methyl-1-(1-[3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropyl]-ethoxymethyl )-2,3,5,6-tetrafluoro-4-methoxymethyl-benzene

20 g of anhydrous DMF was added to a 250 mL four-necked flask, and 1.5 g of NaH was added under a nitrogen atmosphere. 5.2 g of 1-methyl 1-[3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropyl]-ethanol was dissolved in 10 g of DMF and then added dropwise at 20 ° C. The NaH solution in DMF was added dropwise and stirred for 1 hour. 6 g of 1-chloromethyl-2,3,5,6-tetrafluoro-4-methoxymethyl-benzene was dissolved in 30 g of DMF, and added dropwise to the above solution at 5 °C. After the dropwise addition, the mixture was heated to room temperature and stirred for 4 hours. The reaction was quenched by the addition of 200 g of water, and the aqueous phase was extracted with 3*50 mL of ethyl acetate. The organic phase was combined and washed with water to neutral, and then lyophilized to give 6.6 g of pale brown oil, yield 67%, content 97.4%.

This compound is the compound of the present invention 10: 1-methyl-1-(1-[3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropyl]-ethoxy yl) -2,3,5,6-tetrafluoro-4-methoxymethyl - benzene molecular _{formula: C 19 H 22 O 2 F} 4 Cl 2, molecular weight 429.28, molecular ion mass peak of M = 428.500 Molecular magnetic resonance spectroscopy (1H (ppm) CDCl3): 5.63 (d, 1H); 0.87 (t, 1H); 0.53 (t, 1H); 4.67 (S, 2H); 4.63 (S, 2H); s, 3H); 1.26 (s, 6H); 1.11 (s, 6H).

Example 3 Table Compound 12 cis-1-(1-[3-(2,2-dibromo-vinyl)-2,2-dimethyl-cyclopropyl]-ethoxymethyl)-2 Synthesis of 3,5,6-tetrafluoro-4-methoxymethyl-benzene

20 g of anhydrous DMF was added to a 250 mL four-necked flask, and 1.5 g of NaH was added under a nitrogen atmosphere. 6.5 g of cis-1-methyl 1-[3-(2,2-dibromo-vinyl)-2,2-dimethyl-cyclopropyl]-ethanol (prepared from cis-dibromo-chrylic acid) It was dissolved in 10 g of DMF, and then added dropwise to a DMF solution containing NaH at 20 ° C, and the mixture was stirred for 1 hour. 6 g of 1-chloromethyl-2,3,5,6-tetrafluoro-4-methoxymethyl-benzene was dissolved in 30 g of DMF, and added dropwise to the above solution at 5 °C. After the drop, warm up to the room Stir for 4 hours. The reaction mixture was quenched by the addition of 200 g of water, and the aqueous phase was extracted with 3*50 mL of ethyl acetate. The organic phase was combined and washed with water to neutral. After lyophilization column chromatography, 7.6 g of a brown oil was obtained. The yield was 63% and the content was 98.0%.

This compound is the compound of the present invention 12: cis-1-(1-[3-(2,2-dibromo-vinyl)-2,2-dimethyl-cyclopropyl]-ethoxymethyl -2,3,5,6-tetrafluoro-4-methoxymethyl-benzene Molecular formula: C ₁₈ H ₂₀ O ₂ F ₄ Br ₂ , molecular weight 504.15, mass spectrometer molecular ion peak M=504. 500 mega NMR Resonance hydrogen spectrum (1H (ppm) CDCl3): 6.33 (d, 1H); 3.01 (t, 1H); 0.87 (t, 1H); 0.51 (t, 1H); 4.67 (S, 2H); 4.63 (S, 2H); 3.24 (s, 3H); 1.21 (d, 3H); 1.11 (s, 6H).

Example 4 Table Compound 14Z-cis-1-(1-[3-(2-Chloro-2trifluoromethyl-vinyl)-2,2-dimethyl-cyclopropyl]-ethoxymethyl Synthesis of 2,3,5,6-tetrafluoro-4-methyl-benzene

20 g of anhydrous DMF was added to a 250 mL four-necked flask, and 1.5 g of NaH was added under a nitrogen atmosphere. 5.5 g of Z-cis-1-[3-(2chloro-2-trifluoromethyl-vinyl)-2,2-dimethyl-cyclopropyl]-ethanol (by Kungfuyl chloride, hydrogenation The preparation) was dissolved in 10 g of DMF, and then added dropwise to a DMF solution containing NaH at 20 ° C, and the mixture was stirred for 1 hour. 5.8 g of 1-chloromethyl-2,3,5,6-tetrafluoro-4-methyl-benzene was dissolved in 30 g of DMF, and added dropwise to the above solution at 5 °C. After the dropwise addition, the mixture was heated to room temperature and stirred for 4 hours. The reaction mixture was quenched by the addition of 200 g of water, and the aqueous phase was extracted with 3*50 mL of ethyl acetate. The organic phase was combined and washed with water to neutral. After lyophilization column chromatography, 6.4 g of a pale brown oil was obtained. The yield was 65% and the content was 97.7%.

This compound is the compound of the present invention 14: Z-cis-1-(1-[3-(2-chloro-2trifluoromethyl-vinyl)-2,2-dimethyl-cyclopropyl] -ethoxymethyl)-2,3,5,6-tetrafluoro-4-methyl-benzene Molecular formula: C ₁₉ H ₂₀ O ₂ F ₇ Cl, molecular weight 448.80, mass spectrometer molecular ion peak M=448. 1H (ppm) CDCl3: 5.82 (d, 1H); 3.01 (t, 1H); 0.87 (t, 1H); 0.51 (t, 1H); 4.67 (S, 2H); 4.63 (S) , 2H); 3.24 (s, 3H); 1.21 (d, 3H); 1.11 (s, 6H).

Example 5: Compound 2 in Table 1 trans-1-(1-[3-(2,2-difluoro-vinyl)-2,2-dimethyl-cyclopropyl]-ethoxy)- Synthesis of 2,3,5,6-tetrafluorobenzene

20 g of anhydrous DMF was added to a 250 mL four-necked flask, and 1.5 g of NaH was added under a nitrogen atmosphere. 4.7 g of trans-1-[3-(2,2-difluoro-vinyl)-2,2-dimethyl-cyclopropyl]-alcohol (direct hydrogenation of trans-difluthrin methyl ester) The reduction preparation was dissolved in 10 g of DMF, and then added dropwise to a DMF solution containing NaH at 20 ° C, and the mixture was stirred for 1 hour. 5.6 g of 1-chloromethyl-2,3,5,6-tetrafluorobenzene was dissolved in 30 g of DMF, and added dropwise to the above solution at 5 °C. After the dropwise addition, the mixture was heated to room temperature and stirred for 4 hours. The reaction mixture was quenched by the addition of 200 g of water, and the aqueous phase was extracted with 3*50 mL of ethyl acetate. The organic phase was combined and washed with water to neutral, and then lyophilized to give 6.6 g of bright yellow oil. The yield was 69% and the content was 98.2%.

This compound is the compound of the present invention 2: trans-1-(1-[3-(2,2-difluoro-vinyl)-2,2-dimethyl-cyclopropyl]-ethoxy) -2,3,5,6-tetrafluorobenzene Molecular formula: C ₁₅ H ₁₄ OF ₆ , molecular weight 326.28, mass spectrometer molecular ion peak M=326. 500 NMR nuclear magnetic resonance spectrum (1H (ppm) CDCl3): 6.57 (m, 1H); 3.90 (d, 1H); 0.87 (t, 1H); 0.51 (t, 1H); 4.63 (S, 2H); 3.47 (d, 2H); 1.11 (s, 6H).

Test Example 1 for determination of biological activity of rice planthopper

In the rice planthopper, the 3rd instar nymphs raised in the field and cultivated in rice seedlings for many generations were collected.

0.01 g of the compound of the present invention 9, 12 and ethylester were separately taken; dissolved in 0.5 ml of DMF, 0.2 ml of Tween 80 emulsifier was added, and the mixture was stirred uniformly, and 100 ml of the insecticide mother liquid having a concentration of 100 mg/L was added by deionization. Then, 8 ml of the mother liquid was taken, added to water containing 0.1% Tween 80, and diluted to 100 ml to obtain a test solution having a concentration of 8 mg/L. Further, the mixture was diluted with water containing 0.1% Tween 80, and a gradient of 6 concentrations of 4, 2, 1, 0.5, and 0.25 mg/L was obtained in a ratio of 2 times, and the test was carried out.

15 strains of two-leaf and one-core rice seedlings were selected and immersed in the test solution for 30 seconds, then taken out and naturally dried. The roots were moisturized with wet cotton wool, and the plastic wrap was wrapped out. As for the glass test tube (200*30mm), each concentration was 4 Repeat. Then, using a writing brush, the 3rd instar nymphs of rice planthopper, which was lightly anesthetized with ether, were connected, and each tube was 15 positive and negative, and the nozzle was tight with white gauze. After the treatment is completed, as for the observation room.

For data statistics and analysis methods, see NY/T 1154.11-2008 pesticide indoor bioassay test guidelines. The results are shown in the table below.

Test agent	Regression equation	LC 50 mg/L
Compound 9 of the invention	y=1.5978+3.1219x	12.30
Compound 12 of the invention	y=1.6726+3.2159x	10.83
Ethylmethrin	y=0.5938+2.3519x	74.72

Test Example 2 for the control test of cotton aphid

The control effect on the cotton aphid was evaluated by the contact method. The experimental unit included a container with a small opening, and a cotton seedling plant growing for 6-7 days was placed inside. Pre-infection was carried out by placing 30-40 insects on a leaf cut from the cultured plants on the leaves of the test plants. When the leaves dried, the larvae moved to the experimental plants. The soil of the experimental unit is covered with a layer of sand.

0.25 mg/L of the compound of the present invention 1 to 17 was placed in a manner similar to that of Test Example 1, and the test plants were sprayed 3 times, 1 ml each time, and the test unit was air-dried for 1 hour, and then a black sieved hole was placed thereon. The lid was incubated for 6 days at room temperature of 20 degrees at a relative humidity of 50-70%, and the mortality of insects in each experimental unit was examined. Among the test compounds, except for the compound 7, the remaining 16 compounds all obtained mortality of more than 80%.

Test Example 3:

The compound 10 of the present invention and tetrafluthrin were prepared into mosquito coils for efficacy test. 0.014 g of each of the pyrethroids was dissolved in 1 g of kerosene, and dropped into 35 g of blank mosquito scent to make 0.04% mosquito coil. Pipette 20 female Culex pipiens pallens, put them into a closed drum test device, take a piece of tested mosquito coils, put them on the mosquito-repellent incense rack, ignite the mosquito-repellent incense, remove the mosquito-repellent incense after 1min, record at intervals The number of test mosquitoes knocked down, after 20 minutes, all the test mosquitoes were transferred to a clean insect cage, and the number of dead mosquitoes was checked after 24 hours. The results are shown in the table below: it is shown that the compound 10 of the present invention is nearly 1.8 times more effective against mosquitoes than tetrafluthrin.

Mosquito type	Concentration (m/m)	KT 50 (min)	24-hour mortality
Compound 10 of the invention	0.04%	4.4	100%
Tefluthrin	0.04%	7.3	100%

Claims (10)

1. An ether insecticidal compound having a pyrethroid-like structure, characterized in that the structure is as shown in Formula A:

   

   Wherein R ₁ and R ₂ are a methyl group, a halogen atom or a trifluoromethyl group; R ₃ and R ₄ are a H atom, a methyl group or an ethyl group; and R ₅ is a H atom, a methyl group or a methoxymethyl group.
2. The ether-based insecticidal compound according to claim 1, wherein R ₁ and R ₂ are a chlorine atom, R ₃ is a H atom, R ₄ is a methyl group, and R ₅ is a methoxymethyl group. , the compound is of the following structure

   
3. The ether-based insecticidal compound according to claim 1, wherein R ₁ and R ₂ are fluorine atoms, R ₃ and R ₄ are H atoms, and when R ₅ is H, the compound has the following structure.

   
4. The ether-based insecticidal compound according to claim 1, wherein R ₁ is a chlorine atom, R ₂ is a trifluoromethyl group, R ₃ and R ₄ are a methyl group, and R ₅ is a methyl group. The compound is of the following structure

   
5. A method for producing an ether-based insecticidal compound according to any one of claims 1 to 4, which comprises the steps of using an alcohol represented by Formula B and a tetrafluorobenzene halogenated product represented by Formula C as a raw material. And the two are dissolved in an inert solvent such as DMF in the presence of NaH, and subjected to etherification synthesis reaction at room temperature to prepare the ether-like insecticidal compound having a pyrethroid-like structure; the alcohol and tetrafluorocarbon The molar ratio of benzene halide is 1:1;

   
6. Use of an etheric insecticidal compound according to any one of claims 1 to 4 for controlling sanitary pests or agricultural pests.
7. The use according to claim 6, wherein the sanitary pest is a mosquito, a fly, a locust or a cockroach; and the agricultural pest is a rice planthopper.
8. The use according to Claim 6, characterized in that the ether insecticidal compound is prepared as an active ingredient into a conventional preparation for controlling a sanitary pest or an agricultural pest.
9. The use according to claim 8, wherein when the ether-based insecticidal compound is prepared as an active ingredient into a conventional preparation, the conventional preparation includes the ether-based insecticidal compound itself or includes the ether Insecticidal compound And an inert carrier.
10. The use according to claim 9, wherein when the conventional preparation comprises the ether insecticidal compound and an inert carrier, the weight of the ether insecticidal compound is from 0.001 to 95% by weight based on the total weight of the conventional preparation.