CN87100628A - The production method of silicoorganic compound and make the sterilant and the miticide of activeconstituents with it - Google Patents

Abstract

The present invention relates to a class of new organosilicon compound shown in general formula (I) and production method thereof, containing this organosilicon compound (as active ingredient) and diluent, carrier and/or auxiliary agent (such as insect growth regulator) insecticides and acaricides.

Description

The present invention relates to novel organosilicon compounds, which have high insecticidal and acaricidal activity and low toxicity to warm-blooded animals, to processes for the production of these compounds, and to insecticides using these compounds as active ingredients agents and acaricides.

Research on the formation of pyrethrin analogs by modifying the chemical structure of a natural insecticidal component, pyrethrin, is being extensively carried out.

It has been found that compounds represented by the following general formula (VIII) and compounds represented by the following general formula (IX) in which the ester moiety is substituted with other groups have high insecticidal activity.

[The meanings of R ₂ , R ₃ , R ₄ and R ₅ in the formula (VIII) are the same as those in the general formula (I) given later. ], [In the formula (IX), the meanings of R ₂ , R ₃ , R ₄ and R ₅ are the same as in the general formula (I) given below] (see Japanese Patent Laid-Open No. 201737/1983).

These compounds are being widely developed as a new class of insecticides to replace traditional organophosphate insecticides and carbamate insecticides. However, this class of insecticides still has some inherent disadvantages of synthetic pyrethrins, for example, the problem of drug resistance, poor systemic action and high fish toxicity, especially the compounds represented by the general formula (Ⅷ). The above disadvantages are more obvious. These disadvantages have not been completely overcome.

In terms of finding more useful insecticidal and acaricidal components, the present inventors have carried out extensive research and finally found that if silicon atoms are introduced into these compounds to replace the carbon atoms in the main chain, most of the above-mentioned disadvantages can be overcome. The insecticidal activity of the resulting compound is enhanced and the toxicity to warm-blooded animals is reduced. The present invention has been accomplished based on these findings. Why this effect occurs after the introduction of silicon atoms is unclear. It is estimated that this effect may be attributed to the empty third orbital in the outer shell of the atom.

The organosilicon compound of the present invention is represented by the following general formula (I),

In the formula, A represents -CH ₂ -CH ₂ -, -CH=CH- or -CH ₂ -O-; R ₁ represents a methyl group or a group represented by the following general formula (II),

(wherein R _{and R} can be the same or different, each representing a hydrogen atom, a halogen atom, an alkyl group of 1-4 carbon atoms, an alkoxy group of 1-3 carbon atoms, a halogen atom of 1-2 carbon atoms Alkyl or haloalkoxy with 1-2 carbon atoms; R ₄ and R ₅ together can form a methylenedioxy), X represents nitrogen atom or methylene, Y represents oxygen atom, methylene methyl, amino, methylamino, formylamino or carbonyl, _R2 represents a hydrogen atom or a fluorine atom, and _R3 represents a hydrogen atom, a halogen atom or a methyl group.

The compound represented by the above general formula (I) can be prepared by reacting an organosilicon compound represented by the following general formula (IV) with a compound represented by the general formula (V):

In the formula, the meaning of _R is the same as the meaning in the general formula (I), and M represents a chlorine atom or a metal atom such as Li, Na and K,

In the formula, the meanings of A, X, Y, _R2 and _R3 are the same as those in the general formula (I), and Z represents a halogen atom or a reactive derivative.

The reaction is carried out in a suitable solvent, if necessary, with heating in the presence of a catalyst. In the above general formula, when A is a -CH=CH- group, there are geometric isomers due to the double bond. The present invention includes each isomer and mixtures of isomers. The following are typical examples of the mixture represented by the general formula (I). The scope of the present invention is not limited to these compounds.

Dimethyl(4-ethoxyphenyl)[3-(2-phenoxy(6-pyridyl)propyl]silane

n ²⁰ _D 1.5684

Dimethyl(4-ethoxyphenyl)[3-(2-phenoxyphenyl)-1-propenyl]silane

1.5667

Dimethyl(4-ethoxyphenyl)[3-(3-benzoylphenyl)propyl]silane

Dimethyl(4-ethoxyphenyl){3-[2-(4-fluorophenoxy)-6-pyridyl-]propyl}

Dimethyl(4-ethoxyphenyl)[3-(3-phenoxy-4-fluorophenyl)-1-propenyl]

Trimethyl[3-(3-phenoxyphenyl)4propyl]silane

Trimethyl{3-[3-(3-chlorobenzyl)phenyl]propylsilane

Dimethyl(4-chlorophenyl){3-[3-(4-chlorobenzoyl)-4-fluorophenyl]-1-propenyl}silane

Trimethyl{3-[3-(4-methylanilino)-4-fluorophenyl]propyl}silane

Trimethyl{3-[3-(N-methylanilino)phenyl]-1-propenyl}silane

n ²⁰ _D 1.5564

Trimethyl{3-(2-benzyl-3-fluoro-6-pyridyl)-1-propenyl]silane

n ²⁰ _D 1.5558

Trimethyl{3-[2-(4-chlorophenoxy)-6-pyridyl]propyl}silane

n ²⁰ _D 1.5603

Trimethyl[3-(2-benzoyl-6-pyridyl]silane

n ²⁰ _D 1.5570

Dimethyl(3,4-dichlorophenyl){3-[3-(4-fluorophenoxy)-4-fluorophenyl]-1-propenyl}silane n ²⁰ _D 1.5642

Dimethyl(4-difluoromethoxyphenyl){3-[3-(N-formyl-2-bromoanilino)phenyl]-1-propenyl]silane n ²⁰ _D 1.5681

Dimethyl(3,4-methylenedioxyphenyl){3-[2-(N-methyl-4-fluoroanilino)-6-pyridyl]propyl}silane

n ²⁰ _D 1.5720

Dimethyl(4-tert-butylphenyl)[3-(2-anilino-3-fluoro-6-pyridyl)propyl]

Dimethyl(3,4-methylenedioxyphenyl){3-[2-(4-methylbenzoyl)-6-pyridyl]propylsilane n ²⁰ _D 1.5704

Dimethylphenyl{3-[3-(3-methylbenzyl)phenyl]-1-propenyl]silane

n ²⁰ _D 1.5655

Dimethyl(4-methoxyphenyl)[3-(3-anilinophenyl)-1-propenyl]silane

n ²⁰ _D 1.5670

Dimethyl(3-chloro-4-trifluoromethylphenyl){3-[3-(N-methyl-2-fluoroanilino)4-fluorophenyl]-1-propenyl]silane

n ²⁰ _D 1.5729

Dimethyl(3,4-dimethylphenyl)[3-(2-phenyl-6-pyridyl)-1-propenyl]silane n ²⁰ _D 1.5694

Dimethyl(3-chloro-4-ethylphenyl)[3-(benzyl-3-fluoro-6-pyridyl)-1-propenyl]silane n ²⁰ _D 1.5723

Dimethyl(3-methoxy-4-chlorophenyl){3-[2-(4-chloroanilino)-6-pyridyl]-1-propenyl}silane n ²⁰ _D 1.5786

Dimethyl(3-methyl-4-fluorophenyl){3-[2-(N-methylanilino)-6-pyridyl]-1-propenyl}silane n ²⁰ _D 1.5790

Dimethyl(4-isopropylphenyl){3-[2-(N-formyl-4-fluoroanilino-6-pyridyl]-1-propenyl}silane n ²⁰ _D 1.5788

Trimethyl{3-[3-(N-formyl-3-fluoroanilino)phenyl]propyl}silane

Trimethyl{3-[2-(3-methylanilino)-3-fluoro-6-pyridyl]-1-propenyl}silane n ²⁰ _D 1.5595

Trimethyl{3-[2-(N-methylanilino)-6-pyridyl]propyl}silane

n ²⁰ _D 1.5581

Trimethyl{3-[2-(N-formyl-4-fluoroanilino)-6-pyridyl]-1-propenyl}silane n ²⁰ _D 1.5575

Dimethyl(3-bromo-4-bromofluoroethylphenyl)[3-(2-benzyl-6-pyridyl)propyl]silane n ²⁰ _D 1.5779

Dimethyl(3-fluoro-4-propylphenyl){3-[2-(N-formyl-4-bromoanilino)-6-pyridyl]propyl}silane

n ²⁰ _D 1.5802

Dimethyl(4-chlorophenyl)[3-(3-phenoxyphenyl)-1-propenyl]silane

n ²⁰ _D 1.5743

Dimethyl(4-chlorophenyl)[3-(2-phenoxy-3-fluoro-6-pyridyl)-propyl]silane n ²⁰ _D 1.5760

Trimethyl[3-(2-benzoyl-3-fluoro-6-pyridyl)-1-propenyl]silane

n ²⁰ _D 1.5585

Dimethyl(4-difluorochloromethoxyphenyl)[3-(3-benzoyl-4-fluorophenyl)propyl]silane n ²⁰ _D 1.5653

Dimethyl(3-isopropoxyphenyl){3-[3-(N-methyl-3-bromoanilino)phenyl]-1-propenyl]silane

n ²⁰ _D 1.5764

Dimethyl(4-pentafluoroethoxyphenyl)[3-(2-phenoxy-3-fluoro-6-pyridyl)propyl]silane n ²⁰ _D 1.5697

Dimethyl(4-ethoxyphenyl){3-[3-(4-fluorophenoxy)phenyl]-1-propenyl]silane

n ²⁰ _D 1.5669

Dimethyl(4-ethoxyphenyl)[3-(3-phenoxy)phenylpropyl]silane

n ²⁰ _D 1.5641

Dimethyl(4-ethoxyphenyl)(3-phenoxybenzyloxymethyl)silane

n ²⁰ _D 1.5653

Dimethyl(4-ethoxyphenyl)[3-(3-phenoxy-4-fluoro)phenylpropyl]silane

n ²⁰ _D 1.5638

Dimethyl(4-ethoxyphenyl)[3-(3-anilino)phenylpropyl]silane

n ²⁰ _D 1.5690

Dimethyl(4-ethoxyphenyl)(3-benzyl-benzyloxymethyl)silane

n ²⁰ _D 1.5682

Dimethyl(4-ethoxyphenyl){3-[3-(N-methyl-4-chloroanilino)phenyl]propyl}silane

n ²⁰ _D 1.5706

Dimethyl(3,4-dichlorophenyl)[3-(4-fluorophenoxy)-4-fluorobenzyloxymethyl]silane n ²⁰ _D 1.5612

Dimethyl(4-difluoromethoxyphenyl){3-[3-(N-formyl-4-methylanilino)phenyl]propyl}silane n ²⁰ _D 1.5798

Dimethyl(3,4-methylenedioxyphenyl)(3-anilino-4-fluorobenzyloxymethyl)silane

n ²⁰ _D 1.5790

Dimethyl(4-tert-butylphenyl){3-(4-bromobenzyl)phenyl]propyl}silane

n ²⁰ _D 1.5765

Dimethylphenyl{3-(3-phenoxy)phenylpropyl]silane

n ²⁰ _D 1.5477

Dimethyl(4-methoxyphenyl)[3-(N-methylanilino)-4-fluorobenzyloxymethyl]silane n ²⁰ _D 1.5692

Dimethyl(3-chloro-4-trifluoromethylphenyl)[3-(N-formyl-4-fluoroanilino)-4-fluorobenzyloxymethyl]silane

Dimethyl(3-chloro-4-ethylphenyl)[3-(4-bromo-anilino)benzyloxymethyl]silane

n ²⁰ _D 1.5586

Dimethyl(3,4-dimethylphenyl){3-[3-(4-fluorophenoxy)phenyl]propyl}silane

n ²⁰ _D 1.5833

Dimethyl(3-methoxy-4-chloromethylphenyl)[3-(3-benzyl-4-fluorophenyl)propyl]silane n ²⁰ _D 1.5692

Dimethyl(3-methyl-4-fluorophenyl)[3-(4-bromophenoxy)-4-fluorobenzyloxymethyl]silane

Dimethyl(4-isopropylphenyl)[3-(N-methylanilino)benzyloxymethyl]silane

Dimethyl(3-bromo-4-bromofluoromethylphenyl){3-[3-(4-methylphenoxy)-4-fluorophenyl]propyl}silane

Dimethyl(3,4-methylenedioxyphenyl)[3-(4-iodobenzylbenzyloxymethyl)]silane

Dimethyl(4-chlorophenyl){3-[3-(4-fluoroanilino)phenyl]propyl}silane

Dimethyl(3-fluoro-4-propylphenyl)[3-(N-formyl-4-chloroanilino)benzyloxymethyl]silane

Dimethyl(4-difluoromethoxyphenyl)[3-(N-chlorophenoxy-4-fluorobenzyloxymethyl]silane

Dimethyl(4-chlorophenyl)[3-(3-phenoxyphenyl)propyl]silane

Dimethyl(4-chlorophenyl)[3-(4-fluorophenoxy)benzyloxymethyl]silane

n ²⁰ _D 1.5606

Dimethyl(4-fluorophenyl)(3-benzoylbenzyloxymethyl)silane

Dimethyl(3,4-dimethylphenyl)[2-(4-chlorophenoxy)-3-fluoro-6-pyridylmethoxymethyl]silane n ²⁰ _D 1.5729

The compound of the present invention is novel, solid or liquid at normal temperature, and easily soluble in organic solvents. Therefore, it can be used as an insecticide or acaricide in the form of emulsifiable concentrate, oil solution, powder, wettable powder or aerosol. These compounds can also be used as insecticidal or acaricidal fumigants, for example in the form of mosquito coils mixed with a suitable carrier such as wood chips. More effective fumigation can be produced by heating a solution containing the active ingredient or by heating a paper substance impregnated with the agent. Fumigation can also be done with the help of organic gasifiers, which can produce decomposition gases by direct or indirect heating. In this case, the active ingredient is mixed with the invigorating agent and packed in the same container.

Compared with traditional pyrethroids, the compound of the present invention is more stable to light, can effectively kill various pests and mites, has low toxicity to warm-blooded animals and fish, and is relatively low in price. Therefore, it can be used as agricultural and horticultural insecticides and acaricides, replacing traditional organophosphorus insecticides and organochlorine insecticides.

The insecticide and acaricide of the present invention are effective in preventing and controlling health pests such as flies, mosquitoes and cockroaches, and agricultural pests such as black-tailed leafhoppers, light cicadas, rice borers, elephants, cabbage armyworms, diamondback moths, oriental tobacco budworms, It is very effective against seed beetles, noctuids, cabbage caterpillars, leaf rollers, aphids and scale insects. These pests may be organophosphate and carbamate resistant, or non-resistant. The compounds of the present invention are also effective against storage grain pests such as corn weevil and tobacco leaf beetle, ants, termites and mites. The compound of the present invention is useful as an insecticide for rice because it is much less toxic to fish than conventional pyrethroids and has systemic action. The insecticide and acaricide of the present invention can use N-octyl bicycloheptyl diimide (trade name "MGK-264"), N-octyl bicycloheptyl diimide and aryl sulfonate The mixture (trade name "MGK-5026"), synepyrin500, octachlorodipropyl ether, piperonyl butoxide, etc. The insecticide and acaricide of the present invention can be mixed with other insecticides, fungicides, nematocides, herbicides, plant growth regulators, fertilizers, and other agricultural chemicals. Examples of insecticides that can be used in combination include organophosphates such as fenitrothion, dichlorvos, diazinon, trifenfos, and triclophos; Granville; traditional pyrethroids such as pyrethrin, allethrin, pyrethroid, phenothrin, permethrin, cypermethrin, deltamethrin, permethrin, permethrin and fluvalinate and Insecticides such as albutan, chlorophenadimine, and methionium. The resulting mixture is a multi-purpose composition that is synergistic and labor-saving in application. It is most effective when applied in combination with insect growth regulators.

The present inventors' study of the effect of mixing with insect growth regulators is based on the fact that, when applied alone, the compounds of the present invention produce satisfactory insecticidal and acaricidal effects, but lack sufficient ovicidal and hatching-inhibiting effects , and the insects in different growth stages in the field cannot obtain satisfactory control effects. When mixed with insect growth regulators, the compounds of the present invention are capable of controlling larvae, pupae and adults simultaneously due to the remarkable synergy. This mixture is also effective in addressing the problem of predictive resistance.

The aforementioned insect growth regulator is a chitin inhibitor and an insect juvenile hormone that inhibits juvenile molting.

The former is a compound represented by the following general formula (Ⅵ):

In the formula, R ₅ , R ₆ , R ₇ , R ₈ and R ₉ each represent a hydrogen atom, a fluorine atom and a chlorine atom; Y represents a fluorine atom, a chlorine atom, trifluoromethyl, trifluoromethoxy, tetrafluoroethoxy base or

The latter is a compound represented by Mongolia 512, Mongolia 515 or the following general formula (VII)

In the formula, R ₁₀ represents a hydrogen atom or a methyl group, and Z represents a -

The disadvantage of IGRs is that they are slow acting and have little effect on adults when applied alone. This disadvantage is overcome when insect growth regulators are applied in admixture with the compounds of the invention. Mixed application greatly promoted the inhibition of adult reproduction and the inhibition of hatching. As a result, pests and mites can be controlled simultaneously throughout the growing season.

Although it is generally believed that insect growth regulators have little effect on mites, it has been unexpectedly found that the above-mentioned combination significantly increases the acaricidal effect of the insecticides and acaricides of the present invention.

As described above, the insecticides and acaricides of the present invention can be applied in various forms so that they are effective in the control of both domestic pests and agricultural pests. In addition, they are expected to be effective in controlling insects resistant to insecticides. Aspects are also valid.

Examples of insect growth regulators that can be used in the present invention are shown below. However, the scope of the present invention is not limited thereto.

N-(2,6-difluorobenzoyl)-N-(4-chlorophenyl)urea

N-(2-Chlorobenzoyl)-N-(4-trifluoromethoxyphenyl)urea

N-(2,6-difluorobenzoyl)-N-[3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)

N-(2,6-difluorobenzoyl)-N-(2,4-difluoro-3,5-,dichlorophenyl)urea

N-(2,6-difluorobenzoyl)-N-[2,5-dichloro-4-(3-chloro-5-trifluoromethyl-2-

Mongolia five one two

Mongolia five one five

Ethyl N-[2-(4-phenoxy)phenoxyethyl]urethane

O-[2-(4-phenoxy)phenoxyethyl]-propionaldoxime ether

[1-(4-phenoxy)phenoxy]-2-(2-pyridyloxy)propane

The compounds represented by the general formula (VII) have optical isomers due to R ₁₀ and also have geometric isomers when Z is -ON=CHCH ₂ CH ₃ . These isomers are of course included in the present invention.

In the case of a mixed composition, the content of the organosilicon compound and the insect growth regulator as active ingredients may range from 0.01 to 99% by weight, and their mixing ratio may be 1:20 to 20:1. Mixed formulations can be prepared by conventional methods, and they can be administered in combination with solid carriers, liquid carriers, surfactants and other required adjuvants.

The present invention will be further described in detail by some examples below, however, the scope of the present invention is not limited thereto. If not otherwise stated, percentages (%) refer to weight percentages (Wt%)

When R ₁ is a methyl group, organosilicon compounds represented by the general formula (IV) are commercially available. When _R is a group represented by the general formula (II), the compound represented by the general formula (IV) can be easily prepared by the Grignard reaction shown in the reaction equation (I)

Compound (X) can be converted into a lithium compound, sodium compound or potassium compound by reaction with a metal element, if desired.

The compounds of general formula (V) can be easily prepared by using the alcohol component which constitutes the pyrethroid. For example, if A is a -CH ₂ -CH ₂ - group, it can be prepared according to the following reaction equation (2).

Reaction Equation 2

The compound of the above general formula (XI) can be easily coupled with the silicon compound of the general formula (IV) by, for example, Grignard reaction to obtain the compound (I) of the present invention.

If A is a -CH=CH- group, it can be synthesized according to the following reaction equation (3). That is, the compound of general formula (XI) undergoes α-bromination with N-bromosuccinimide. The resulting compound is then subjected to selective dehydrobromination to obtain a compound of general formula (XII). The compound obtained as above undergoes a coupling reaction with the silicon compound of the general formula (IV) and the double bond is displaced in the presence of, for example, n-butyllithium.

Synthetic Example 1

Lithium metal (0.4 g) was added to 50 ml of anhydrous tetrahydrofuran under nitrogen. A solution of dimethyl(4-ethoxyphenyl)chlorosilane (4.2 g) and anhydrous tetrahydrofuran (20 ml) was added dropwise over 30 minutes under cooling to -50°C with a dry ice-acetone mixture. The reaction was carried out at this temperature for 1 hour. The temperature of the liquid was slowly raised to 0°C, and the liquid was stirred for 1 hour to obtain lithium silane. The reaction solution was cooled to -20°C, and a solution of 3-(2-phenoxy-6-pyridyl)propyl chloride (5.0 g) and anhydrous tetrahydrofuran (40 ml) was added dropwise over 1 hour. The liquid was stirred at room temperature for 2 hours. Water was carefully added dropwise to the reaction liquid while cooling to decompose excess lithium. After extraction with benzene, the benzene solution was washed with saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. Benzene was distilled off under reduced pressure. The resulting oil was purified by column chromatography packed with 100 g of silica gel. Finally, 6.2 g of dimethyl(4-ethoxyphenyl[3-(2-phenoxy-6-pyridyl)phenyl]silane, the above-mentioned compound (1) was obtained.

Synthetic example 2

In 40ml of anhydrous ether, add 0.6g of metal magnesium chips, 1.5g of 3-[3-(4-chlorobenzoyl)-4-fluorophenyl]-2-propenyl bromide and a small amount of iodine. The reaction was started by heating the reactants to 40°C. While keeping the liquid boiling, a solution of 3-[3-(4-chlorobenzoyl)-4-fluoro]-2-propenylbromide (5,6 g in diethyl ether (20 ml)) was added dropwise.

Stirring was continued for 15 minutes to obtain the Grignard reagent. A solution of dimethyl(4-chlorophenyl)chlorosilane (4.2g) in diethyl ether (50ml) was added dropwise over 3 hours with vigorous stirring. Stirring was continued for 1 hour at reflux. A mixture of ice (30g), ammonium chloride (10g) and water (20g) was added with stirring. The ether layer was separated. The aqueous layer was extracted twice with 50 ml of ether, and the extract was combined with the above ether layer. After washing with aqueous sodium chloride, diethyl ether was distilled off. The resulting residue was dissolved in 50 ml of anhydrous tetrahydrofuran. The solution was cooled to -50°C, and 16 ml of n-butyl lithium (1.35 mol) in n-hexane was added under nitrogen protection. The reaction was continued at the same temperature, stirred overnight, the reaction solution was heated to room temperature, and the reaction was completed. Cool the reaction solution to -50°C, add 30ml of 10% hydrochloric acid, and extract with ethyl acetate. The ethyl acetate solution was washed twice with saturated sodium chloride solution, followed by drying over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography. Finally, 7.5 g of dimethyl(4-chlorophenyl){3-[3-(4-chlorobenzoyl)-4-fluorophenyl]-1-propenyl}silane, namely the above-mentioned compound (8) was obtained . In the same way as Synthetic Example 1, trimethyl {3-[3- (4-Methylanilino)-4-fluorophenyl]propyl}silane, i.e. the composition (9) above.

In the same manner as Synthetic Example 2, from dimethyl (3-chloro-4-ethylphenyl) chlorosilane and 3-(2-benzyl-3-fluoro-6-pyridyl)-2-propenyl bromide Magnesium chloride, which can be used to obtain dimethyl(3-chloro-4-ethylphenyl)[3-(2-benzyl-3-fluoro-6-pyridyl)-1-propenyl]silane, the above compound (twenty three).

Synthetic Example 3

Lithium metal (0.4 g) was added to 50 ml of anhydrous tetrahydrofuran under nitrogen protection. After cooling to -50°C with a dry ice-acetone mixture, a solution of dimethyl(4-chlorophenyl)chlorosilane (4.1 g) in anhydrous tetrahydrofuran (20 ml) was added dropwise over 30 minutes. After 1 hour at this temperature, the reaction is complete. The temperature of the liquid was slowly raised to 0°C, and the liquid was stirred for 1 hour to obtain lithium silane. The reaction solution was cooled to -20°C, and a solution of 3-(3-phenoxy)phenylpropyl chloride (4.9 g) in anhydrous tetrahydrofuran (40 ml) was added dropwise over 1 hour. The liquid was stirred at room temperature for 2 hours. Carefully drop it into the reaction solution under cooling to decompose excess lithium. After extraction with benzene, the benzene solution was washed with a saturated sodium chloride solution, followed by drying with anhydrous sodium sulfate. The oil obtained by distilling off benzene under reduced pressure was purified by column chromatography packed with 100 g of silica gel. Finally, 6.4 g of dimethyl(4-chlorophenyl)[3-(3-phenoxyphenyl)propyl]silane, the above-mentioned compound (63), was obtained.

Synthetic Example 4

Add metal potassium (0.9g) to 40ml of anhydrous ether under nitrogen protection. The resulting suspension was cooled to -40°C and a solution of dimethyl(4-methoxyphenyl)chlorosilane (4.0g) in anhydrous ether (20ml) was added dropwise over 30 minutes. After stirring at -40°C for 2 hours, the liquid temperature slowly rose to 0°C. Stirring was continued for 1 hour and the reaction was complete, forming potassium silane. The reaction solution was cooled to -40°C again, and 3-(N-methylanilino)-4-fluorobenzyloxymethyl chloride (5, 6g) in anhydrous ether was added dropwise within 1 hour under the protection of nitrogen ( 40ml) solution. The reaction was continued for 1 hour at -40°C and overnight at room temperature. Water was added to the solution, ether was separated and the solvent was distilled off, and the obtained residue was purified by column chromatography packed with 100 g of silica gel. Obtained 6,8 g of dimethyl(4-methoxyphenyl)[3-(N-methylanilino)-4-fluorobenzyloxymethyl]silane, namely the above compound (51)

In the same manner as above, dimethyl (3-methoxy-4-chloromethylphenyl) sodium silane and 3-(3-benzyl-4-fluorophenyl) propyl bromide were obtained from dimethyl ( 3-methoxy-4-chloromethylphenyl)[3-(3-benzyl-4-fluorophenyl)propyl]silane, the above compound (55), can also be obtained from dimethyl(3- Dimethyl(3-fluoro-4-propylphenyl base)[3-(N-formyl-4-chloroanilino)benzyloxymethyl]silane, namely the above-mentioned compound (61).

The following are the biological activity test results of the composition provided by the invention.

Test example 1 Insecticidal effect experiment of spraying

The following sample solutions were prepared from each compound of the invention.

Solution (A): Kerosene solution containing 0.2% compound

Solution (B): kerosene solution containing 0.2% compound and 0.8% synergist synepirin500

Solution (C): kerosene solution containing 0.1% compound and 0.1% pyrethrum

For comparison, solution (A) was also prepared by dissolving 0.2% of pyrethrum and 0.2% of compound (A) (further described later).

The sample solution was used for houseflies, the hit ratio was observed and the relative potency was calculated. At the same time, get the death rate after 24 hours (numbers in parentheses)

Compound Solution (A) Solution (B) Solution (C)

Pyrethrum 2.15 (34) - -

Compound (A) 1.32 (59) - -

(1) 2.48 (100) 4.33 (100) 2.42 (100)

(2) 2.61 (100) 4.58 (100) 2.46 (100)

(3) 2.54 (100) 4.27 (100) 2.34 (100)

(4) 2.64 (100) 4.60 (100) 2.51 (100)

(5) 2.39 (100) 4.25 (100) 2.33 (100)

(6) 2.28 (100) 4.09 (100) 2.27 (100)

(7) 2.16 (100) 3.65 (100) 2.25 (100)

(8) 2.20 (100) 3.93 (100) 2.26 (100)

(9) 2.07 (100) 3.70 (100) 2.20 (100)

(10) 2.29 (100) 3.94 (100) 2.28 (100)

(11) 2.31 (100) 4.06 (100) 2.31 (100)

(12) 2.15 (100) 3.72 (100) 2.26 (100)

(13) 2.35 (100) 4.23 (100) 2.32 (100)

(14) 2.40 (100) 4.37 (100) 2.37 (100)

(15) 2.29 (100) 4.21 (100) 2.28 (100)

(16) 2.17 (100) 3.90 (100) 2.26 (100)

(17) 1.98 (92) 3.74 (100) 2.19 (100)

(18) 1.69 (72) 2.96 (94) 1.97 (87)

(19) 1.72 (75) 3.04 (94) 2.04 (92)

(20) 2.39 (100) 4.35 (100) 2.31 (100)

(21) 2.06 (90) 3.92 (100) 2.23 (100)

(22) 2.14 (97) 3.70 (100) 2.25 (100)

(23) 1.80 (84) 3.53 (100) 2.09 (97)

(24) 1.65 (75) 2.98 (97) 2.02 (87)

(25) 1.79 (84) 3.66 (100) 2.10 (100)

(26) 2.01 (94) 3.91 (100) 2.24 (100)

(27) 2.13 (97) 3.87 (100) 2.26 (100)

(28) 1.96 (92) 4.02 (100) 2.22 (100)

(29) 2.30 (100) 4.39 (100) 2.31 (100)

(30) 2.27 (100) 4.30 (100) 2.28 (100)

(31) 1.71 (78) 2.88 (94) 2.05 (92)

(32) 1.65 (72) 2.93 (92) 1.97 (90)

(33) 2.48 (100) 4.51 (100) 2.34 (100)

(34) 2.52 (100) 4.49 (100) 2.36 (100)

(35) 2.34 (100) 4.26 (100) 2.33 (100)

(36) 2.09 (97) 3.74 (100) 2.20 (100)

(37) 2.55 (100) 4.60 (100) 2.41 (100)

(38) 2.16 (100) 4.08 (100) 2.32 (100)

(39) 2.53 (100) 4.65 (100) 2.44 (100)

(40) 2.63 (100) 4.61 (100) 2.57 (100)

(41) 2.45 (100) 4.30 (100) 2.39 (100)

(42) 2.58 (100) 4.73 (100) 2.46 (100)

(43) 2.50 (100) 4.27 (100) 2.34 (100)

(44) 2.36 (100) 4.18 (100) 2.33 (100)

(45) 2.21 (100) 3.82 (100) 2.25 (100)

(46) 2.16 (97) 3.64 (100) 2.27 (100)

(47) 2.14 (94) 3.70 (100) 2.25 (100)

(48) 2.42 (100) 4.29 (100) 2.38 (100)

(49) 2.53 (100) 4.42 (100) 2.44 (100)

(50) 2.30 (100) 4.05 (100) 2.31 (100)

(51) 2.41 (100) 4.29 (100) 2.35 (100)

(52) 1.98 (92) 3.75 (100) 2.17 (100)

(53) 2.07 (90) 3.96 (100) 2.20 (100)

(54) 1.78 (78) 3.14 (92) 1.98 (92)

(55) 1.69 (70) 2.93 (90) 1.96 (84)

(56) 1.90 (84) 3.38 (100) 2.13 (100)

(57) 2.15 (97) 3.57 (100) 2.24 (100)

(58) 1.86 (80) 3.59 (100) 2.02 (100)

(59) 1.93 (94) 3.80 (100) 2.19 (100)

(60) 2.42 (100) 4.35 (100) 2.35 (100)

(61) 1.89 (90) 3.71 (100) 2.07 (100)

(62) 2.24 (100) 4.08 (100) 2.24 (100)

(63) 2.55 (100) 4.62 (100) 2.49 (100)

(64) 2.59 (100) 4.67 (100) 2.46 (100)

(65) 2.28 (100) 4.13 (100) 2.31 (100)

(66) 2.05 (92) 3.95 (100) 2.18 (100)

Compound (A)

(Japanese Patent Publication No.201737/1980)

Test example 2 Insecticidal effect test of fumigation

A mosquito-repellent coil containing 0.5% of the compound of the present invention as an active ingredient was prepared. According to the method in "Bochu Kagaku Vol.16 (1951), P 176" by Nagasawa and Katsuta, the effect of killing mosquito adults (house mosquito pipiens) of these samples was tested. The relative hit efficiency was calculated, and the results were as follows. The sample number refers to the above Compounds of the invention.

Sample Probability Unit 4 Probability Unit 5 Probability Unit 6

Acrylic pyrethrum 1.00 1.00 1.00

(2) 1.78 1.81 1.85

(7) 1.61 1.64 1.68

(10) 1.65 1.69 1.73

(14) 1.59 1.62 1.64

(19) 1.41 1.43 1.47

(23) 1.50 1.54 1.56

(28) 1.53 1.56 1.59

(31) 1.47 1.50 1.53

(36) 1.72 1.75 1.78

(41) 1.83 1.86 1.90

(45) 1.61 1.64 1.67

(49) 1.79 1.82 1.84

(52) 1.40 1.45 1.48

(54) 1.41 1.43 1.46

(63) 1.85 1.88 1.92

Test example 3 Insecticidal test of local spraying

The compounds of the invention were dissolved in acetone alone or administered in combination with twice the amount of butanosperm (synergist) as active ingredient. Use a micro spray gun to spray the acetone solution onto the thorax and back of adult flies. Mortality after 24 hours was calculated and the relative insecticidal activity and synergism of butanoside compared with the control compound was calculated. The result is as follows.

Relative insecticidal activity with synergists

Ratio of sample increase

relative insecticidal activity

Control ＊ ＊ 1.00 1.52 1.5

(1) 5.04 10.08 2.0

(4) 4.91 10.31 2.1

(11) 3.72 8.18 2.2

(16) 3.49 7.33 2.1

(21) 4.14 8.69 2.1

(29) 4.80 9.60 2.0

(35) 3.95 8.30 2.1

(40) 5.24 10.48 2.0

(42) 6.04 12.08 2.0

(48) 4.70 10.34 2.2

(51) 3.97 8.34 2.1

(59) 3.65 8.40 2.3

(64) 5.59 11.18 2.0

^＊ Comparative compound:

Dissolve 0.4 part of compound (13) of the present invention, 0.1 part of pyrethrum and 1.5 parts of octachloro-dipropyl ether in 28 parts of pure kerosene to prepare a kind of aerosol, then the gained solution is mixed with 70 parts of propellant (liquefied petroleum gas) in an aerosol can.

Formulation example 5

Uniformly mix 0.5g of the compound (17) of the present invention, 0.5g of BHT and 99.0 parts of a carrier consisting of the powder of pyrethrum flowers left after extraction, sawdust and starch by a conventional method to make a mosquito-repellent incense.

Formulation Example 6

Uniformly mix 0.4g of the compound (25) of the present invention, 1.0g of MGK-5026 and 98 parts of carriers by conventional methods to make mosquito coils.

Formulation example 7

A 0.3% powder was prepared by mixing 0.3 part of the present compound (30) and 99.7 parts of clay.

Formulation Example 8

A wettable powder was prepared by mixing 40 parts of the present compound (38), 35 parts of diatomaceous earth, 20 parts of clay, 3 parts of dodecylsulfonate and 2 parts of carboxymethylcellulose.

Formulation Example 9

0.2 part of the present compound (40) was dissolved in water and made up to 100 parts in total with kerosene to prepare a 0.2% oil solution.

Formulation Example 10

An oily solution was prepared by dissolving 0.2 part of the non-invention compound (43) and 0.8 part of butanobuterol in kerosene and making up to a total of 100 parts with kerosene.

Formulation Example 11

20 parts of the present compound (46), 10 parts of Solpole SM-200 (a registered trademark of Toho Kagaku) and 70 parts of mixed xylenes were mixed to obtain a 20% emulsifiable concentrate.

Formulation example 12

Dissolve 0.4 part of compound (48) of the present invention, 0.1 part of pyrethrum and 1.5 parts of octachloro-dipropyl ether in 28 parts of pure kerosene, then, the gained solution is mixed with 70 parts of propellant (liquefied petroleum gas) Put them together in an aerosol can to make an aerosol.

Formulation Example 13

Uniformly mix 0.5 g of the compound (53) of the present invention, 0.5 g of BHT and 99.0 parts of a carrier consisting of extracted pyrethrum powder, sawdust and starch by a conventional method to prepare mosquito coils.

Formulation example 14

Uniformly mix 0.4g of the compound (56) of the present invention, 1.0g of MGK-5026 and 98, and 6g of carrier to make mosquito coils by a conventional method.

Formulation Example 15

A 0.3% powder was prepared by mixing 0.3 part of the present compound (60) and 99.7 parts of clay.

Formulation example 16

A wettable powder was prepared by mixing 40 parts of the present compound (63), 35 parts of diatomaceous earth, 20 parts of clay, 3 parts of dodecylsulfonate and 2 parts of carboxymethylcellulose.

Formulation Example 17

An oil solution was prepared by dissolving 0.2 part of the present compound (7) and 0.5 part of the insect growth regulator (G) in kerosene and making up to 100 parts in total with kerosene.

Formulation Example 18

An oil solution was prepared by dissolving 0.2 part of the present compound (21), 0.1 part of the insect growth regulator (B) and 0.8 part of butanobuterol in kerosene and making up the total to 100 parts with kerosene.

Formulation example 19

An emulsifiable concentrate was prepared by mixing 10 parts of the present compound (48), 10 parts of the insect growth regulator (E), 10 parts of Solpole SM-200 (a registered trademark of Toho Kagaku) and 70 parts of xylene.

Formulation Example 20

Dissolve 0.4 part of compound (52) of the present invention, 0.4 part of insect regulator (J), 0.2 part of pyrethrum and 1.5 parts of octachlorodipropyl ether in 27.5 parts of pure kerosene, then, the gained solution is mixed with 70 parts propellant (liquefied petroleum gas) together in an aerosol can to make an aerosol.

Formulation example 21

Uniformly mix 0.5g of the compound (55) of the present invention, 0.8g of the insect growth regulator (A), 0.6g of BHT and 98.1g of a carrier composed of the powder of pyrethrum flowers remaining after extraction, sawdust and starch by a conventional method to prepare Into mosquito coils.

Formulation Example 22

A powder was prepared by mixing 0.3 part of the present compound (58), 0.2 part of an insect growth regulator and 99.5 parts of clay.

Formulation Example 23

Mix 20 parts of the compound (60) of the present invention, 20 parts of insect growth regulator (C), 35 parts of diatomaceous earth, 20 parts of clay, 3 parts of dodecylsulfonate and 2 parts of carboxymethylcellulose to prepare A wettable powder was obtained.

Formulation Example 24

Dissolve 0.1 part of compound of the present invention (63) and 0.5 part of insect growth regulator (F) in 7 parts of propanol, then, the gained solution is mixed with 91.5 parts of propellant (F11/F12/dimethyl ether=24/80/ 9) Put them together into an aerosol can to make an aerosol.

Test example 4

The emulsifiable concentrate prepared according to the method of formulation example 3 was tested, respectively containing compounds of the present invention (3), (8), (10), (13), (17), (22), (25), (31) , (34), (38), (42), (46), (49), (52), (57), (61), (64), or (66). Apply the 1000-fold diluted emulsion to the radish field at the 5-6 leaf stage severely infested by green peach aphid, and the dosage is 1000L/ha. After two days of observation, it was found that the density of pests in all test fields was reduced to less than one-tenth.

Test example 5

The emulsifiable concentrate prepared in the same way as formulation example 3 has been tested and contains compounds of the present invention (2), (4), (8), (12), (15), (18), (23), ( 29), (33), (41), (43), (46), (50), (54), (56), or (62). Cabbage leaves are dipped in the emulsion diluted 2000 times for 5 seconds. After drying, the cabbage leaves were placed in Petri dishes and 10 healthy cabbage armyworm larvae were released on the day of dipping and five days after dipping. The mortality rate after 24 hours was calculated and the results are as follows.

Sample The day of immersion Five days after immersion

Kill anti-pine emulsifiable oil 40 (%) 5 (%)

(2) 100 100

(4) 100 100

(8) 100 95

(12) 100 95

(15) 95 85

(18) 95 90

(23) 90 80

(29) 95 80

(33) 100 100

(39) 100 100

(41) 100 100

(43) 100 100

(46) 100 100

(50) 95 90

(54) 95 80

(56) 90 80

(62) 100 95

Test example 6

Wettable powders prepared in the same manner as in Formulation Example 8 have been tested, respectively containing compounds (2), (6), (9), (11), (16), (19), (24) of the present invention , (28), (35), (41), (45), (48), (53), (58), (63), or (65). The wettable powder solution diluted 4000 times is applied to broad beans with a compressed air sprayer, and the dosage is 10 ml/pot. Each broad bean plant was infested with about 200 aphids for 1 day before spraying. The infestation of aphids was observed two days after application, and it was found that there was no injury in all tests.

Test example 7

The powder prepared in the same way as Formulation Example 7 has been tested and contains compounds of the present invention (1), (5), (8), (14), (17), (21), (26), ( 30), (33), (37), (40), (44), (47), (51), (56), or (60), respectively, at the bottom of a deep Petri dish with a diameter of 14 cm Spread various powder samples evenly, the dosage is 2g/m. Butter the walls of the Petri dish, but leave the lower part about 1 cm wide. Ten German cockroach adults were released in each Petri dish and allowed to contact the powder for 30 minutes. Transfer the roaches to a new container. Mortality after three days was higher than 80% in all trials.

Test example 8

The emulsifiable concentrate prepared in the same way as formulation example 3 has been tested and contains compounds of the present invention (4), (8), (10), (15), (20), (22), (27), ( 32), (36), (43), (46), (49), (54), (59) or (61). Each emulsion diluted to 100 ppm (active ingredient) was sprayed onto the kidney beans on the turntable in an amount of 10 ml/pot. Five days after sowing the beans, pre-release female adult red mite infestation, 10 on each leaf, and place it at room temperature of 27°C for 1 day. After 10 days, count the number of mites on the bean leaves. All experimental samples were superior to the controls. The result is as follows

The number of mites on each leaf after 10 days of the sample

Kaile San (control) 32

(4) 1

(8) 2

(10) 2

(15) 4

(20) 1

(22) 1

(27) 3

(32) 4

(36) 1

Control 148

(43) 1

(46) 2

(49) 1

(54) 5

(59) 3

(61) 2

Control 2

Test example 9

The toxicity of the compounds of the present invention to fish (carp) was examined according to the test method described in the circular No B-2735 (1965/11.25) of the Ministry of Agriculture and Forestry. Compounds of the present invention which have been examined are (2), (8), (11), (16), (21), (29) and (35). Their TLm48 (ppm) was higher than 10. Other compounds of this invention that have been tested are (41), (47), (50), (55), and (60). Their TLm48 (ppm) was higher than 20.

The following are test examples in which the compound of the present invention is used in combination with an insect growth regulator.

Test example 10

An emulsifiable concentrate containing 20% active ingredient (and an insect growth regulator) was diluted to a predetermined concentration. This dilute solution (20 ml) was sprayed on cages containing 50 male and female flies each. The same dilute solution (20 ml) was also sprayed on 30 housefly larvae (4 days old) placed in a culture medium (consisting of 15 g of wheat bran, 3 g of feed powder and 25 g of water). The container for the larvae is placed in the cage. Count the number of adult flies in the cage at regular intervals. The corrected density index is obtained according to the following equation:

Corrected density index = (A×B)/(C×D)×100

In the formula, A: the number of adult flies before treatment in the untreated group

B: Number of adult flies after treatment in the treatment group

C: Number of adult flies treated in the untreated group

D: Number of adult flies before treatment in the treatment group

The results are listed in the table.

Spray Concentration Corrected Density Index

Sample (ppm) 1 day 5 days 15 days 30 days

(1) 50 0 0 16 28

(C) 5 95 94 70 55

(1)/(C) 50/5 0 0 2 1

(22) 50 4 2 13 26

(I) 5 98 98 54 37

(22)/(I) 50/5 0 0 1 3

(34) 50 0 0 18 31

(E) 5 96 93 67 49

(34)/(E) 50/5 0 0 0 0 1

(40) 50 0 0 18 25

(D) 5 97 98 61 33

(40)/(D) 50/5 0 0 4 2

(41) 50 0 0 22 39

(F) 5 95 94 70 48

(41)/(F) 50/5 0 0 0 0 3

(42) 50 0 0 20 35

(J) 5 98 98 55 30

(42)/(J) 50/5 0 0 1 0

(44) 50 0 1 28 40

(A) 10 95 92 68 53

(44)/(A) 50/10 0 0 7 5

(47) 50 0 0 17 29

(E) 5 97 96 60 47

(47)/(E) 50/5 0 0 0 0 2

(49) 100 2 1 19 37

(I) 5 93 88 47 31

(49)/(I) 100/5 0 0 6 4

(54) 100 5 11 26 41

(B) 10 98 96 71 58

(54)/(B) 100/10 1 3 12 8

(57) 100 2 6 18 30

(H) 5 96 97 64 51

(57)/(H) 100/5 0 1 8 3

(61) 100 3 2 25 39

(C) 5 95 92 65 47

(61)/(C) 100/5 0 1 6 3

(65) 50 0 0 14 26

(G) 5 94 89 66 54

(65)/(G) 50/5 0 0 1 1

The test results show that the insecticide and acaricide containing only the compound of the present invention present a quick-acting effect on the adult flies of the housefly. Day density recovery. On the other hand, the test results also showed that the insect growth regulator applied alone has little effect on adult flies in a short period of time after application, and it slowly exerts its effect when young flies grow into adults.

In contrast, a composition comprising a compound of the present invention and an insect growth regulator becomes effective immediately after application and maintains a low density of adult flies for a long period thereafter. Such a remarkable control effect cannot be expected from the effect of the compounds of the present invention or insect growth regulators alone. Apparently, this remarkable effect should be attributed to the synergistic effect of the two compounds.

Test example 11

The orange leaves were cut into discs with a diameter of 1.5 cm using a punch. The cut leaves were placed on wet filter paper in polystyrene cups with a diameter of 7 cm. Ten citrus red mites (female adults) were infested on each garden leaf. Dilute solutions (2 ml) containing the compounds of the present invention and/or insect growth regulators and spreaders at prescribed concentrations were sprayed on each garden leaf. Spraying is performed using a rotating spray tower. Mortality was tested after 48 hours and acaricidal activity was available. Calculate LC50 and get relative efficiency. The results are listed below.

The relative efficiency of the mixing ratio to [Ⅰ]

Sample [Ⅰ]:[Ⅱ]

(43) 1 0 1.0

(A) 0 1 ＜0.01

(43)/(A) 1 1 2.2

3 1 2.8

(51) 1 0 1.0

(I) 0 1 ＜0.01

(51)/(I) 3 1 3.4

10 1 1.7

(59) 1 0 1.0

(D) 0 1 0.02

(59)/(D) 1 1 2.5

3 1 2.9

(62) 1 0 1.0

(F) 0 1 ＜0.01

(62)/(F) 3 1 3.1

10 1 1.4

(18) 1 0 1.0

(G) 0 1 ＜0.01

(18)/(G) 1 1 2.5

3 1 3.0

Note: [I] represents the compound of the present invention.

[II] represents an insect growth regulator.

The test results show that the use of the compound of the present invention can greatly synergize the insect growth regulators with very low insecticidal activity.

Test example 12

The cabbage infested by a large number of cabbage moths is sprayed with 2000-fold diluted emulsion at a rate of 1000 liters per hectare. This emulsifiable concentrate is prepared according to the same method as formulation example 19, and each emulsifiable concentrate contains (7)+(I), (9)+(E), (14)+(D), (17)+(J), (19) respectively )+(H), (24)+(A), (33)+(F), (48)+(B), or (66)+(C). 2 days and 1 month after application, it was found that the total number of larvae and adults was reduced to 20% or less of that before application, while in the case of the control group where the compound of the present invention was applied alone, the total number recovered after 1 month. The test results clearly show the synergistic effect of insect growth regulators.

Test Example 13

Powders prepared in the same manner as in Formulation Example 22 have been tested, and each powder contains (6)+(B), (11)+(G), (13)+(F), (16)+(J) respectively , (21)+(H), (35)+(A), (47)+(F) or (58)+(E). Sprinkle the above powder evenly on a deep Petri dish with a diameter of 14 cm, and the dosage is 2 g/m ² . Butter the walls of the Petri dish (excluding the lower part, which is about 1 cm wide). Ten adult German cockroaches were placed in each Petri dish and allowed to contact the powder for 30 minutes. Transfer the roaches to a new container. In all experiments, the mortality after three days was higher than 90%. The surviving cockroaches cannot reproduce due to sexual impairment.

File Name Page Line Line Before Correction After Correction

Manual 9 2 〔3-( 〔3-(2-

16 6-7 dimethyl (3-chloro-4 dimethyl (3,4-dimethyl

-ethylphenyl) [3 phenyl) {3-[3-(4-

-(4-bromo-aniline fluorophenoxy)phenyl]propyl}

base) benzyloxymethyl] silane

Silane

16 9-10 dimethyl (3,4- dimethyl (3-chloro-4-

Dimethylphenyl) {3-[3 basephenyl)[3-(4-bromo

-(4-fluorophenoxy)-anilino)benzyloxymethyl]

Phenyl]propyl}silane Silane

18 9 〔3-(N- 〔3-(4-

19 9 -6-pyridine basic pyridin-6-yl

Claims (22)

1. A class of organosilicon compounds represented by general formula (I),

Wherein A represents a -CH ₂ -CH ₂ - group, -CH=CH- group or -CH ₂ -O- group; R ₁ represents a methyl group or a group represented by general formula (II):

(wherein R _{and R} can be the same or different, each representing a hydrogen atom, a halogen atom, an alkyl group of 1-4 carbon atoms, an alkoxy group of 1-3 carbon atoms, a halogen atom of 1-2 carbon atoms Substituted alkyl or halogen of 1-2 carbon atoms represents an alkoxy group, R ₄ and R ₅ can be combined to form a methylenedioxy group); X represents a nitrogen atom or a methine group; Y represents an oxygen atom, methylene, amino, methylamino, formylamino or carbonyl; _R2 represents a hydrogen atom or a fluorine atom, and _R3 represents a hydrogen atom, a halogen atom or a methyl group. 2. The organosilicon compound as defined in claim 1, which is a compound represented by the general formula (III), Wherein A represents -CH ₂ -CH ₂ - group, -CH=CH- group or -CH ₂ -O- group; R ₄ and R ₅ can be the same or different, each represents a hydrogen atom, a halogen atom, 1-4 carbon Atomic alkyl, 1-3 carbon atom alkoxyl, 1-2 carbon atom haloalkyl or 1-2 carbon atom haloalkoxy, _R4 and _R5 can be linked together form a methylenedioxy group; X represents a nitrogen atom or a methine group; Y represents an oxygen atom, methylene, amino, methylamino, formamido or carbonyl; _R2 represents a hydrogen atom or a fluorine atom; _R3 represents A hydrogen atom, a halogen atom or a methyl group. 3. The organosilicon compound as defined in claim 1 or 2, which is a compound represented by the following chemistry.

4. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula.

5. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula.

6. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula.

7. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula.

8. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula. 9. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula.

10. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula.

11. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula.

12. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula.

13. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula.

14. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula.

15. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula. 16. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula. 17. The organosilicon compound defined in claim 1 or 2, which is a compound represented by the following chemical formula.

18. The production method of the organosilicon compound represented by the general formula (I),

In the formula, A represents a -CH ₂ -CH ₂ - group, -CH=CH- group or -CH ₂ -O- group; R ₁ represents a methyl group or a group represented by the following formula (II):

(In the formula, _R4 and _R5 can be the same or different, each representing a hydrogen atom, a halogen atom, an alkyl group with 1-4 carbon atoms, an alkoxy group with 1-3 carbon atoms, and a halogenated group with 1-2 carbon atoms Substituted alkyl or haloalkoxy with 1-2 carbon atoms, R ₄ and R ₅ can be connected together to form a methylenedioxy); X represents a nitrogen atom or a methine group; Y represents an oxygen atom, methylene, amino, methylamino, formylamino or carbonyl; _R2 represents a hydrogen atom or a fluorine atom; _R3 represents a hydrogen atom, a halogen atom or a methyl group, The method comprises reacting an organosilicon compound represented by the following general formula (IV) with a compound represented by (V),

wherein A, X, Y, R ₁ , R ₂ and R ₃ have the same meanings as defined above; M represents a chlorine atom or a metal atom, and Z represents a halogen atom or a reactive derivative. 19. An insecticide and acaricide comprising an organosilicon compound represented by the following general formula (I), a diluent, a carrier and/or an adjuvant,

In the formula, A represents a _-CH2 - _CH2 -base, CH=CH-base or _-CH2- O-base; _R1 represents a methyl group or a group represented by the following general formula (II):

(In the formula, _R4 and _R5 can be the same or different, each representing a hydrogen atom, a halogen atom, an alkyl group with 1-4 carbon atoms, an alkoxy group with 1-3 carbon atoms, and a halogenated group with 1-2 carbon atoms Substituted alkyl or haloalkoxy with 1-2 carbon atoms, R ₄ and R ₅ can be connected together to represent methylenedioxy); X represents nitrogen atom or methine; Y represents oxygen atom, methylene Methyl, amino, methylamino, formylamino or carbonyl; _R2 represents a hydrogen atom or a fluorine atom; _R3 represents a hydrogen atom, a halogen atom or a methyl group. 20. The insecticide and acaricide as defined in claim 19, wherein said adjuvant is an insect growth regulator. 21. The insecticide and acaricide as defined in claim 19 or 20, wherein said insect growth regulator is a chitin inhibitor represented by the following general formula (VI),

In the formula, R ₅ , R ₆ , R ₇ , R ₈ and R ₉ each represent a hydrogen atom, a fluorine atom and a chlorine atom, and Y represents a fluorine atom, a chlorine atom, trifluoromethyl, trifluoromethoxy, tetrafluoroethoxy base or

group. 22. The insecticide and acaricide as defined in claim 19 or 20, wherein the insect growth regulator is 512, 515 or a juvenile hormone compound represented by the following general formula (VII),