JPH06336406A - Insecticidal composition containing hydrazine derivative as active component - Google Patents

Abstract

PURPOSE:To obtain an insecticidal composition containing a specified hydrazine derivative and N1-[(6-chloro-3-pyridyl)methyl]-N2-cyano-N1 methylacetamidine, viable spores of Bacillus thuringiensis or a crystalline toxin produced therefrom. CONSTITUTION:This insecticidal composition is produced by blending one or more kinds of hydrazine derivatives of the formula [A and B each are O, S, C(=O), etc.; R1 to R4 each are H, a halogen, an alkyl, etc.; R5 and R7 each are H, a halogen, an alkyl, nitro, amino, etc.; R8 to R10 each are H, a halogen, an alkyl, nitro, formyl, an alkenly, etc.; R11 is H, cyano, a haloalkylthio, an acyl, a dialkylcarbamoyl, etc.; R<12> is an alkyl; (n) is 0 or 1] with one substance selected from N1-[(6-chloro-3-pyridyl)methyl]-N2-cyano-N1-methylacetamidine, viable spores of Bacillus thuringiensis and a crystalline toxin produced therefrom. Since this composition exhibits a cooperative effect and a synergistic effect, it enables cost reduction, reduction of the number of application and reduction of the dosage required for exhibiting its effect.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel insecticidal composition having an excellent insecticidal action.

[0002]

2. Description of the Related Art Conventionally, various chemicals such as organophosphorus, carbamate, pyrethroid and phenylurea have been developed as insecticides and have been used as single agents and admixtures. However, conventional insecticides have insecticidal spectrum, insecticidal activity at each developmental stage of pests, lack of balance of rapid-acting, residual effect, penetrative transferability, etc., and toxicity to fish even if excellent in terms of insecticidal effect, In addition, the use scene, the number of times of use and the like are limited due to the safety against useful insects and natural enemies, or the chemical damage to crops, so that the insecticidal effect is not necessarily satisfactory. In particular, pests that have recently been reduced in sensitivity to various conventional agents, such as leafhoppers and planthoppers, planthoppers, Nikameichu, which have resistance to organophosphorus agents and carbamate agents in the rice field of Japan, organophosphorus agents in various horticultural crop scenes. , Carbamate agents, spider mites and aphids against pyrethroids, organophosphorus agents in vegetable scenes, carbamate agents, pyrethroids, whitefly against phenylurea agents, organic phosphorus agents in fruit scenes, carbamate agents, pyrethroid agents, phenylureas For example, organic phosphorus agents, carbamate agents, pyrethroid agents, cotton heliotis and spodoptera for phenylurea agents, potato potato beetle, etc. have appeared overseas.

[0003]

Therefore, there is a strong demand for establishment of control technology for these harmful insects.

Further, in recent years, there has been a strong demand for cost reduction for the control of these pests and insects, and it is necessary to obtain a high control effect with a small number of times of spraying and a small amount of applied drug. Therefore, it is required to develop a drug which can meet these requirements. ing.

Under the circumstances as described above, the present inventor has selected N1-[(6-chloro-
3-Pyridyl) methyl] -N2-cyano-N1-methylacetamidine and at least one selected from Bacillus thuringiensis live spores and produced crystal toxins cannot be obtained by using both of them alone. The present inventors have earnestly studied from the viewpoint that a new insecticidal composition having synergistic and synergistic insecticidal effects and having satisfactory toxicity can be obtained.

[0006]

As a result, the expression

[0007]

[Chemical 5]

(Where A and B are the same or different and O, S,

[0009]

[Chemical 6]

Or NR '(where

[0011]

[Chemical 7]

Or in the case of NR ', a double bond can be formed with the adjacent carbon atom), R ₁ , R ₂ , R ₃
And R ₄ is the same or different hydrogen atom, halogen atom,
(C ₁ -C ₄ ) alkyl group, (C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkyl group or benzyloxy (C ₁
-C ₄₎ an alkyl group, R _5, R _6, and R ₇ are each independently hydrogen atom, a halogen atom, (C ₁ -
C ₄ ) alkyl group, nitro group, amino group, cyano group, hydroxyl group, formyl group, (C ₁ -C ₄ ) haloalkyl group,
(C ₂ -C ₄₎ alkenyl, (C ₁ -C ₄₎ alkoxy, (C ₁ -C ₄₎ alkoxy (C ₁ -C ₄₎ alkyl group, (C ₁ -C ₄₎ alkylthio (C ₁ - C ₄₎ alkyl or (C ₁ -C _4,) alkoxy (C ₁ -
C ₄ ) alkoxy group is shown, and R ₈ , R ₉ and R ₁₀ are each independently a hydrogen atom, a halogen atom, or (C ₁ -C
₄ ) alkyl group, tri (C ₁ -C ₄ ) alkylsilyloxy (C ₁ -C ₄ ) alkyl group, nitro group, (C ₁ -C 4
₄ ) haloalkyl group, hydroxy (C ₁ -C ₄ ) alkyl group, formyl group, (C ₁ -C ₄ ) alkoxy group, (C
₂ -C ₄₎ alkenyloxy group, (C ₂ -C ₄₎ alkynyloxy group, (C ₂ -C ₄₎ alkenyl group, _{(C 1}
-C ₄ ) haloalkoxy group, (C ₁ -C ₄ ) haloalkylthio group, (C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkoxy group, and a phenyl group which may be substituted with a halogen atom ( C ₁ -C ₄ ) alkoxy group, or C
F _{3 represents} a (C ₁ -C ₄ ) alkoxy group having a phenoxy group which may be substituted with halogen, or a (C ₁ -C ₂ ) alkyl group, and R ₁₁ represents a hydrogen atom, a cyano group, or (C ₁
-C ₄ ) haloalkylthio group, (C ₂ -C ₅ ) acyl group, di (C ₁ -C ₄ ) alkylcarbamoyl group, (C ₁
-C ₄₎ alkoxycarbonyl group, (C ₁ -C ₄₎ alkoxycarbonyl group, (C ₂ -C ₄₎ alkenyl group or a halogen atom,, (C ₁ -C ₄₎ alkoxy, (C ₁ -C ₆ ) Is an alkylcarbonyloxy group or a (C ₁ -C ₄ ) alkoxycarbonyl group which may be substituted with a (C ₁ -C ₄ ) alkyl group, and R ₁₂ is (C
It indicates a branched alkyl group having ₃ -C _10), n represents 0 or 1.

However, R represents a hydrogen atom, a (C ₁ -C ₄ ) alkyl group or a (C ₁ -C ₄ ) alkoxy group,
R 'is a hydrogen atom, (C ₁ -C ₄₎ alkyl group, (C ₂ -
C ₄ ) acyl group or formula

[0014]

[Chemical 8]

The p-fluorobenzyl group is represented by R and R'may form a dioxolane ring together with the carbon atom to which they are bonded. In the general formula (1), examples of the halogen atom include fluorine, chlorine, bromine and iodine atoms, and examples of the (C ₁ -C ₄ ) alkyl group include methyl, ethyl, n-propyl, isopropyl and n. -Butyl, isobutyl, sec-butyl, ter
t-butyl, and examples of the (C ₂ -C ₄ ) alkenyl group include allyl, 2-propenyl, 1-propenyl, ethenyl and 2-butenyl groups, and (C ₁ -C 4).
₄ ) Examples of the alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy,
Examples thereof include isobutoxy, sec-butoxy and tert-butoxy groups, and examples of hydroxy (C ₁ -C ₄ ) alkyl groups include 2-hydroxyethyl or hydroxymethyl, and (C ₁ -C ₄ ) alkoxy (C
The ₁ -C ₄₎ alkoxy, such as ethoxy, methoxy, methoxyethoxy, ethoxyethoxy, n- propoxy methoxy, include isopropoxyphenyl methoxy or n- butoxy methoxy group, the (C ₂ ~C ₄₎ alkynyl group, Examples thereof include an ethynyl group, a propynyl group, and a butynyl group. Examples of the (C ₁ -C ₄ ) haloalkyl group include 1- or 2-chloroethyl, chloromethyl, dichloromethyl, bromomethyl, 1- or 2
-Bromoethyl, fluoromethyl, difluoromethyl or trifluoromethyl group, and the like, (C ₁ -C
₄ ) As the haloalkoxy group, for example, 1- or 2
-Bromoethoxy, 3-bromo-n-propoxy, 2,
2,2- or 1,1,1-trifluoroethoxy or trifluoromethoxy group may be mentioned, (C _2-
C ₄₎ The alkenyloxy group, for example allyloxy or 2-butenyloxy group and the like, (C ₂ -C
₄ ) Examples of the alkynyloxy group include a propargyloxy or butynyloxy group, which has a phenyl group which may be substituted with a halogen atom (C _1-
As the C ₄ ) alkoxy group, for example,

[0016]

[Chemical 9]

Examples of the (C ₁ -C ₄ ) alkylthio (C ₁ -C ₄ ) alkyl group include methylthiomethyl, 2-methylthioethyl, 3-isopropylthiopropyl, n-butylthiomethyl or 2 -Ethylthioethyl group, and the tri (C ₁ -C ₄ ) alkylsilyloxy (C ₁ -C ₄ ) alkyl group includes, for example, trimethylsilyloxymethyl, trimethylsilyloxyethyl or dimethyl-tert-butylsilyloxymethyl group. And the like. Examples of the (C ₁ -C ₄ ) alkoxy group having a phenoxy group which may be substituted with CF ₃ , halogen or a (C ₁ -C ₂ ) alkyl group include

[0018]

[Chemical 10]

Examples of the (C ₁ -C ₄ ) haloalkylthio group include 2-chloroethylthio, 2-bromoethylthio, trichloromethylthio, fluorodichloromethylthio, trifluoromethylthio and 2-fluoropropyl groups. Examples of the (C ₂ ~C ₅₎ acyl groups such as acetyl, propionyl and the like groups can be mentioned, (C ₁ ~C ₄₎ alkoxycarbonyl group, for example tert- butoxycarbonyl, methoxycarbonyl carbonyl or include ethoxycarbonyl group, the (C ₁ ~C ₄₎ alkoxycarbonyl group, for example ethoxycarbonyl, methoxycarbonyl, include isopropoxycarbonyl or isobutoxycarbonyl group, (C ₁ ~
C ₆₎ alkylcarbonyloxy group or (C ₁ -C
₄ ) As the (C ₁ -C ₄ ) alkyl group which may be substituted with an alkoxycarbonyl group, for example, ethylcarbonyloxymethyl, 2-isopropylcarbonyloxyethyl, tert-butylcarbonyloxymethyl,
Examples thereof include 2-methoxycarbonylethyl and tert-butoxycarbonylmethyl groups. Examples of the (C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkyl group include ethoxymethyl, 3-methoxypropyl, 2-ethoxyethyl,
A methoxyethyl group may be mentioned, and the di (C ₁ -C ₄ ) alkylcarbamoyl group may be, for example, a dimethylcarbamoyl group or a diethylcarbamoyl group, and a (C ₃ -C ₄
The C ₁₀₎ branched alkyl group, for example tert- butyl, 1,2,2-trimethyl propyl, 2,2-dimethylpropyl or 1,2,2-trimethyl-butyl group.

Typical examples of the hydrazine derivative represented by the formula (1) used in the present invention include the following.

N- (5-methyl-1,4-benzodioxane-6-carbo) -N'-t-butyl-N'-
(3,5-Dimethylbenzoyl) hydrazine (Compound 1) N- (5-methylchroman-6-carbo) -N'-t
-Butyl-N '-(3,5-dimethylbenzoyl) hydrazine (Compound 2) -N-cyano-N- (5-methyl-1,4-benzodioxane-6-carbo) -N'-t-butyl- N'-
(3,5-Dimethylbenzoyl) hydrazine (Compound 3) N- (N ", N" -di-n-butylaminosulphenyl) -N- (5-methyl-1,4-benzodioxane-6) -Carbo) -N'-t-butyl-N '-(3,5
-Dimethylbenzoyl) hydrazine (Compound 4) N-[(N "-isopropyl-N" -isopropoxycarbonylamino) sulfenyl] -N- (5-methylchroman-6-carbo) -N'-t -Butyl-N '
-(3,5-Dimethylbenzoyl) hydrazine (Compound 5) N- (5-methyl-1,4-benzodioxane-6-
Carbo) -N'-t-butyl-N '-(3,5-dichlorobenzoyl) hydrazine (Compound 6) N- (5-methyl-1,4-benzodioxane-6-
Carbo) -N'-1,2,2-trimethylpropyl-
N '-(3,5-dichlorobenzoyl) hydrazine (Compound 7) N- (5-methylchroman-6-carbo) -N'-t
-Butyl-N '-(3,5-dichlorobenzoyl) hydrazine (Compound 8) -N-cyano-N- (5-methylchroman-6-carbo) -N'-t-butyl-N'-(3. 5-Dimethylbenzoyl) hydrazine (Compound 9) N- (5-methylchroman-6-carbo) -N'-t
-Butyl-N '-(3,5-dimethyl-4-fluorobenzoyl) hydrazine (Compound 10) -N- (5-methylchroman-6-carbo) -N-trichloromethylthio-N'-t-butyl-N '-(3,5
-Dimethylbenzoyl) hydrazine (Compound 11) N- (5-methyl-1,4-benzodioxane-6-
Carbo) -N '-(2,2-dimethylpropyl-N'-
(3,5-Dimethylbenzoyl) hydrazine (Compound 1
2) N- (5-methyl-1,4-benzodioxane-6-
Carbo) -N-trichloromethylthio-N'-t-butyl-N '-(3,5-dimethylbenzoyl) hydrazine (Compound 13) N- (5-methyl-1,4-benzodioxane-6-
Carbo) -N'-t-butyl-N '-(3-fluoromethyl-5-methylbenzoyl) hydrazine (Compound 1
4) N- (5-methyl-1,4-benzodioxane-6-carbo) -N '-(1,2,2-trimethylpropyl)-
N '-(3,5-Dimethylbenzoyl) hydrazine (Compound 15).

However, the compound is not limited to these compounds.

One specific N1-[(6-chloro-3-pyridyl) methyl] -N2-cyano-N1-methylacetamidine and Bacillus thuringiensis live spores and crystalline toxins to be mixed are as follows. The following are listed.

N1-[(6-chloro-3-pyridyl)
Methyl] -N2-cyano-N1-methylacetamidine (Compound 16) -Bacillus thuringiensis subspecies,
As Koustaki ・ Turiside (SDS Biotech Co., Ltd.) ・ Dipole (Sumitomo Chemical Co., Ltd.) ・ Toarrow CT (Toagosei Kagaku Kogyo Co., Ltd .; Compound 1)
7).

Hydrazine compounds and N1-[(6-chloro-3-pyridyl) methyl] -N2-cyano-N1-
Unexpectedly, the activity of a mixture of methylacetamidine and at least one drug selected from live spores of Bacillus thuringiensis and crystalline toxin produced is unexpectedly larger than the sum of the respective active compounds (active compound Both exhibit excellent synergistic action and synergistic action), and have excellent fast-acting property and residual effect.

The insecticidal composition according to the present invention is applied for the purpose of controlling pests in agricultural and horticultural crops, forests, turf, stored grains, clothing and hygiene, for example, in control pests of cruciferous vegetables. It shows a cooperative and synergistic insecticidal effect at a lower concentration than a single active compound alone against a certain diamondback moth, Nikameichu which is an important insect pest of paddy rice, and Chacococcinus angustifolium which is an important insect pest of fruit trees, and has an excellent fast-acting effect. And shows residual effect.

The weight ratio of active compounds in the insecticidal compositions according to the invention is generally N1-[(6-chloro-3-pyridyl) methyl] per part by weight of the hydrazine derivative of the formula (1).
-N2-cyano-N1-methylacetamidine and at least one drug selected from live spores of Bacillus thuringiensis and crystal toxin produced, usually 0.05 to 10
Parts by weight, preferably 0.1 to 10 parts by weight.

The insecticidal composition of the present invention exhibits excellent insecticidal activity and can be used by foliage spraying, water or water surface application, irrigation treatment on the soil surface, and soil admixture treatment.

Since the insecticidal composition of the present invention exhibits strong insecticidal activity at a lower dose than when each active compound is used alone, it is possible to avoid phytotoxicity to crops, and conventional insecticides alone cannot be used. Insufficient balance of insecticidal spectrum, insecticidal activity at the developmental stage of pests, fast-acting effect, residual effect, osmotic transferability, etc.Although excellent in insecticidal effect, it is toxic to fish or safe against useful insects and natural enemies. It can also be used in situations where use is restricted due to problems such as sex or phytotoxicity to crops.

The insecticidal composition of the present invention comprises leafhoppers such as leafhopper leafhoppers such as rice leafhoppers and leafhoppers such as rice leafhoppers, planthoppers such as brown planthoppers, white-tailed planthoppers, and brown leafhoppers, and lepidopteran insects such as Nikameichu and Cobnomeiga. , Pleurotus spp., Etc. and Coleoptera pests such as Weevil Weevil, Rice weevil, Inedrooimushi, etc., Lepidopteran pests of garden crops such as fruit trees, vegetables, tea, etc. Aphids, scale insects, whitefly, white leafhopper, etc., thrips pests such as Thrips palmiaceae, etc. It can be used for.

The insecticidal composition of the present invention is in the form of a mixed preparation which can be taken by general agricultural chemicals, such as emulsion, wettable powder, powder, granules,
It may be in the form of powder, tablet, water solution, flowable agent, spray agent, or the like.

Although the content ratio of the active ingredient in the insecticidal composition of the present invention varies depending on the purpose of use, the content of the emulsion, wettable powder, etc. is 5 to 7.
0% by weight is suitable, 0.1-15% by weight is suitable as the granule, and these concentrations may be appropriately changed depending on the purpose of specification. When using emulsions, wettable powders, etc.
For example, it is diluted with water or the like by a factor of 100 to 10,000 and sprayed.

The liquid carrier (solvent) used is, for example, water, alcohols, ketones, ethers, aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons,
Solvents such as acid amides and esters are suitable, and these can be appropriately used by mixing one kind or two or more kinds at a suitable ratio.

As the solid carrier, vegetable powder, mineral powder, diatomaceous earth, calcium carbonate, alumina, sulfur powder, activated carbon and the like are used, and these may be used alone or in admixture of two or more in an appropriate ratio. it can.

Examples of the surfactant used as an emulsifier, a spreading agent, a penetrating agent, a dispersant, etc. include, for example, sodium dodecylbenzene sulfonate, dialkyl sulfosuccinate, sodium dialkyl sulfosuccinate, sodium laurate and higher alcohol sulfate. sodium,
Sodium lignin sulfonate, polyoxyethylene alkylaryl ether sulfate, β-naphthalene sulfonate sodium formalin condensate, dinaphthalene methanesulfonate, alkylaryl sulfonate,
Anionic surfactants such as sodium alkylaryl sulfonate and sodium alkylnaphthalene sulfonate, polyoxyethylene nonylphenyl ether, polyoxyethylene oleyl ether, polyoxyethylene oleic acid ester, polyoxyethylene alkylaryl ether, polyoxyethylene Alkyl ether,
Polyoxyethylene sorbitan monolaurate, polyoxyethylene fatty acid ester, polyoxyethylene styryl phenyl ether, sorbitan monooleate, sorbitan monolaurate, sorbitan monostearate,
Examples thereof include nonionic surfactants such as sorbitan sesquioleate, sorbitan palmitate, acetylene glycol, diglycerin borate monostearate.

The insecticidal compositions according to the invention are in the form of use adjusted according to their formulation, with other active compounds such as the compound of formula (1) and N1-[(6-chloro-3-pyridyl) methyl]-. Insecticides, fungicides, acaricides, nematicides, fungicides other than at least one agent selected from N2-cyano-N1-methylacetamidine and Bacillus thuringiensis live spores and produced crystal toxins , Can be used as a mixture with a growth regulator. The insecticidal composition of the present invention thus obtained is less toxic, is a safe and excellent pesticide, can be used in the same manner as conventional insecticides, acaricides, as a result, compared to conventional products And can exert an excellent effect.

The insecticidal composition of the present invention can be used for target pests by, for example, spraying foliage of crops, spreading insect bodies, applying water to paddy fields, or treating soil. The application rate can be varied over a wide range depending on the application time, application place, application method, etc., but generally, the active ingredient (the compound of the formula (1) and N
1-[(6-chloro-3-pyridyl) methyl] -N2-
At least one drug selected from cyano-N1-methylacetamidine and live spores of Bacillus thuringiensis and crystalline toxins produced is used in an amount of 1 to 1,000 g, preferably 10 to 1,000 g. It is desirable to use.

[0038]

EXAMPLES Examples of the insecticidal composition of the present invention are shown below, but the present invention is not limited thereto. In the examples, "parts" means "parts by weight".

Formulation Example 1. Emulsion Emulsion was prepared by dissolving 5 parts of compound 1 and 5 parts of compound 16 in 80 parts of a mixed solution of dimethyl sulfoxide and xylene, and mixing an alkylphenol ethylene oxide condensate with calcium alkylbenzenesulfonate and polyoxyethylenated castor oil. And This product is diluted with water and used as a spray.

Formulation Example 2. Wettable powder 5 parts of compound 2 and 15 parts of compound 17 are mixed with 10 parts of white carbon, 20 parts of kaolin, 22.5 parts of clay and 20 parts of diatomaceous earth, and further a mixture of sodium laurate and sodium ligninsulfonate. 5 parts were mixed and finely pulverized to obtain a wettable powder. This product is diluted with water and used as a spray solution.

Formulation Example 3. Dust agent To 0.5 part of compound 4 and 0.5 part of compound 16, a mixture of 2 parts of white carbon, talc and calcium carbonate was added and mixed and ground to give a powder. Disperse this product as it is before use.

Formulation Example 4. Granules 1 part of compound 5 and 2 parts of compound 16 are mixed with 33 parts of bentonite fine powder, 64 parts of talc, and 2 parts of sodium lignin sulfonate, and then water is added and kneaded until uniform. Next, the mixture was granulated through an injection molding machine and passed through a granulator and a dryer screen to obtain granules having a grain size of 0.8 mm. This product is used by spraying it directly on the paddy field and soil surface.

Formulation Example 5. Oil agent 0.1 part of compound 2 and 0.1 part of compound 16 were dissolved in 5 parts of dimethyl sulfoxide and mixed with 0.5 part of piperonyl butoxide and white kerosene to obtain an oil agent. This product is used as it is.

Next, the fact that the insecticidal composition of the present invention exhibits excellent activity will be specifically described with reference to test examples.

The biological effects of the insecticidal composition of the present invention will be specifically described with reference to test examples.

Test Example 1. Insecticidal effect test against Spodoptera litura, the insecticidal composition of the present invention and each single agent were diluted to a predetermined concentration with water, and cabbage leaves were immersed for about 20 seconds. After air-drying, the third-instar larvae of Spodoptera litura in a 9 cm diameter plastic container
I put the lid on with 0 heads. 5-6 small holes were opened in the container. The number of live and dead insects was investigated 4 days after the release, and abnormal insects and dead insects were added, and the half-lethal concentration was calculated as the number of dead insects. The test was conducted in a two-district system. The results are shown in Table 1.

[0047]

[Table 1] Insecticidal effect against Spodoptera litura Hydrazine hydrazine hydrazine Compound compound (0.2ppm) Compound (0.2ppm) Compound concentration Mortality rate + Compound 16 (1ppm) + Compound 17 (1ppm) (ppm) (%) Dead insect Rate (%) Mortality rate (%) None − 0 0 0 Compound 1 0.2 30 100 100 Compound 2 0.2 20 20 100 100 Compound 3 3 0.2 15 100 100 Compound 4 4 0.2 20 100 100 100 Compound 5 0.2 15 100 100 compound 6 0.2 0 100 100 compound 7 0.2 5 100 100 compound 8 0.2 0 100 100 compound 9 0.2 0 100 100 100 compound 10 0.2 5 100 100

[0048]

The insecticidal composition of the present invention has an excellent synergistic effect, as is apparent from the above test.

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Shinji Yokoi 1041 Sansu Yasu-cho, Yasu-cho, Yasu-gun, Shiga In-house (72) Inventor Reiji Ichinose 1041 Yasu-machi Yasu-cho, Yasu-gun, Shiga In-house

Claims (1)

[Claims] Claims: Where A and B are the same or different, and O,
S, [Chemical formula 2] Or NR '(provided that Or in the case of NR ', a double bond can be formed with the adjacent carbon atom), R ₁ , R ₂ , R ₃ and R ₄ are the same or different hydrogen atom, halogen atom, (C _1-
C ₄₎ alkyl group, (C ₁ -C ₄₎ alkoxy (C ₁ -
C ₄₎ alkyl group or benzyloxy (C ₁ -C ₄₎
Represents an alkyl group, and R ₅ , R ₆ and R ₇ are each independently a hydrogen atom, a halogen atom, a (C ₁ -C ₄ ) alkyl group, a nitro group, an amino group, a cyano group, a hydroxyl group, a formyl group, ( C ₁ -C ₄₎ haloalkyl group, (C ₂ -
C ₄₎ alkenyl group, (C ₁ -C ₄₎ alkoxy group,
(C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkyl group,
A (C ₁ -C ₄ ) alkylthio (C ₁ -C ₄ ) alkyl group or a (C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkoxy group, wherein R ₈ , R ₉ and R ₁₀ are each independently A hydrogen atom, a halogen atom, a (C ₁ -C ₄ ) alkyl group, a tri (C ₁ -C ₄ ) alkylsilyloxy (C
₁ -C ₄₎ alkyl group, a nitro group, (C ₁ -C ₄₎ haloalkyl group, hydroxy (C ₁ -C ₄₎ alkyl group, a formyl group, (C ₁ -C ₄₎ alkoxy groups, (C ₂ -
C ₄₎ alkenyloxy group, (C ₂ -C ₄₎ alkynyloxy group, (C ₂ -C ₄₎ alkenyl, (C ₁ -
C ₄₎ haloalkoxy group, with a (C ₁ -C ₄₎ haloalkylthio group, (C ₁ -C ₄₎ alkoxy (C ₁ -C ₄₎ alkoxy group, a phenyl group optionally substituted by a halogen atom (C ₁ -C ₄₎ alkoxy group or CF _3,,
A (C ₁ -C ₄ ) alkoxy group having a phenoxy group which may be substituted with halogen or a (C ₁ -C ₂ ) alkyl group, and R ₁₁ represents a hydrogen atom, a cyano group or (C _1-
C ₄₎ haloalkylthio group, (C ₂ -C ₅₎ acyl group,
Di (C ₁ -C ₄ ) alkylcarbamoyl group, (C ₁ -C
₄₎ alkoxycarbonyl group, (C ₁ -C ₄₎ alkoxycarbonyl group, (C ₂ -C ₄₎ alkenyl group or a halogen atom,, (C ₁ -C ₄₎ alkoxy, (C ₁ -C ₆₎ alkyl A carbonyloxy group or a (C ₁ -C ₄ ) alkoxycarbonyl group which may be substituted with (C ₁ -C ₄ ) alkyl group, wherein R ₁₂ is (C ₃
Represents a branched alkyl group of —C ₁₀ ), and n represents 0 or 1. Here, R represents a hydrogen atom, (C ₁ -C ₄₎ alkyl or (C ₁ -C ₄₎ alkoxy group, R 'is a hydrogen atom, (C ₁ -C ₄₎ alkyl group, (C ₂ -C ₄ ) Acyl group or formula The R- and R'may form a dioxolane ring together with the carbon atom to which they are attached. ), N1-[(6-chloro-3-pyridyl) methyl] -N2-cyano-N1-methylacetamidine and Bacillus thuringiensis live spores and produced crystals. An insecticidal composition comprising one selected from toxins.