JPH0940643A - Cyanoalkyl heterocyclic compound and insecticide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound having potent insecticidal activity on insect pests and harmful animal parasites, etc., without bringing raised plants to chemical injuries, thus useful as an insecticide. SOLUTION: This new compound, a cyanoalkyl heterocyclic compound, is expressed by formula I [R is a 1-5C alkyl-bearing cyanoalkyl; A is an (alkyl- substituted) 2-3C saturated hydrocarbon chain divalent group, etc.; a lone bond between A and X (indicated as →) is monovalent or divalent; X is NH, N, O, S, CH or CH2 ; Y is nitro; where, when X is NH, A is an (alkyl-substituted) 2-3C unsaturated hydrocarbon chain divalent group, while, when X is N, A is an (alkyl-substituted) 2-3C unsaturated hydrocarbon chain trivalent group and the lone bond is divalent], e.g. 3-(2-cyanoethyl)-2-cyanoiminotetrahydro-1,3- thiazine. The compound of formula I is obtained, for example, by reaction between a compound of formula II and a compound of the formula R-Hal (Hal is a halogen).

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to cyanoalkyl-
The present invention relates to a heterocyclic compound, a method for producing the same and use thereof as an insecticide.

[0002]

2. Description of the Related Art Japanese Unexamined Patent Publication (Kokai) No. 48-910 disclosed before the filing date of the present application
JP-A-64 discloses a compound represented by the following general formula, which is useful as an intermediate in the production of bactericidal, antidiabetic, virus-sedative and diuretic active substances, Has been described.

Embedded image (In the formulae, the groups R ₁ and R ₂ are each a hydrogen atom or 1 to 4
A straight-chain or branched lower alkyl group having 4 carbon atoms, ..., R ₃ and R ₄ are hydrogen atoms, a straight-chain or branched lower alkyl group having 1 to 4 carbon atoms Lower alkyl group, ..., R ₅ is a hydrogen atom, a linear or branched lower alkyl group having 1 to 6 carbon atoms, a hydroxyalkyl group having 2 to 3 carbon atoms, Optionally mono- by a halogen atom, a lower alkyl or alkoxy group having 1 or 2 carbon atoms
Or a di-substituted phenyl group, a benzyl or phenethyl group optionally mono-substituted by a halogen atom ... X is an oxygen or sulfur atom or a nitrogen atom thereof having 1 to 4 carbon atoms, A linear or branched lower alkyl group or benzyl or an optionally substituted imino group, and n equals 0 or 1)

Similarly, British Patent Application Publication No. 2,055,
No. 796-A describes that the compound represented by the following formula has insecticidal activity.

Embedded image (In the formula, X, NH -, - N (alkyl) -, - S- or -CH ₂ -, R is hydrogen, alkyl or alkylcarbonyl and n represents 2 or 3, R is hydrogen or X is - N
H-has its tautomerism)

[0004]

The present inventors have now found a cyanoalkyl-heterocyclic compound of formula (I) below. formula:

Embedded image In the formula, R represents a cyanoalkyl group, A represents a divalent group of a saturated hydrocarbon chain having 2 to 3 carbon atoms which may be optionally substituted, or a carbon number which may be optionally substituted. Two
~ 3 represents a divalent or trivalent group of an unsaturated hydrocarbon chain,
The bond “→” between X and N is monovalent or divalent, and X is N
H, N, O, S, CH or CH ₂ is shown, and Y is a cyano group or a nitro group. Here, when X represents NH, A represents a divalent group of an optionally substituted unsaturated hydrocarbon chain having 2 to 3 carbon atoms, and when X represents N, A is optional. Represents a trivalent group of an unsaturated hydrocarbon chain having 2 to 3 carbon atoms which may be substituted with, and the bond “→” between A and X represents divalent.

The compound of the formula (I) of the present invention can be synthesized, for example, by the following method. Production method a): Formula

[Chemical 6] In the formula, A, X and Y are the same as the above, and a compound represented by the formula R-Hal (III), wherein R is the same as the above and Hal represents a halogen atom. The method for producing a cyanoalkyl-heterocyclic compound of the above formula (I), characterized in that

Process b): [In the formula (I), A represents a divalent group of an optionally substituted saturated hydrocarbon chain having 2 to 3 carbon atoms, and X represents O or S. , A is A ¹ ,
X is X ¹ ] Formula: R—NH—A ¹ —X ¹ H (IV) In the formula, R, A ¹ and X ¹ are the same as the above, and a compound represented by the formula:

[Chemical 7] Wherein Y is the same as above, and B is a methylthio group or an amino group.

Embedded image In the formula, R, A ¹ , X ¹ and Y are the same as defined above, and a process for producing a cyanoalkyl-heterocyclic compound.

The cyanoalkyl-heterocyclic compounds of formula (I) according to the invention show a strong insecticidal action. According to the invention, the cyanoalkyl-heterocyclic compounds of the formula (I) surprisingly and surprisingly have a substantially very excellent insecticidal action compared to, for example, the compounds described in the publications cited above. Reveal

In the compound of the formula (I) of the present invention, R is preferably cyanoalkyl having 1 to 5 carbon atoms, and A is optionally alkyl substituted 2 to 3 carbon atoms. A divalent group of a saturated hydrocarbon chain or a divalent or trivalent group of an optionally substituted alkyl-unsaturated hydrocarbon chain having 2 to 3 carbon atoms is shown, and a bond between A and X is "→". Is monovalent or divalent, and X is NH, N, O, S,
CH or CH ₂ and Y represents cyano or nitro, and when X represents NH, A is a divalent group of an optionally substituted unsaturated hydrocarbon chain having 2 to 3 carbon atoms. When X represents N, A represents a trivalent group of an unsaturated hydrocarbon chain having 2 to 3 carbon atoms which may be alkyl-substituted.

Further, in the formula (I), it is particularly preferable that R represents cyanoalkyl having alkyl having 1 to 3 carbon atoms, and A represents 2 to 2 carbon atoms which may be methyl-substituted.
3 represents a divalent group of a saturated hydrocarbon chain of 3 or a divalent or trivalent group of an unsaturated hydrocarbon chain of 2 to 3 carbon atoms which may be methyl-substituted, and represents a bond between A and X. → "indicates monovalent or divalent, and X is NH, N, O, S, CH or CH ₂
And Y represents cyano or nitro, where X
When NH represents NH, A represents a divalent group of an unsaturated hydrocarbon chain having 2 to 3 carbon atoms which may be methyl-substituted, and X
When N represents N, A represents a trivalent group of an unsaturated hydrocarbon chain having 2 to 3 carbon atoms which may be methyl-substituted.

Specific examples of the compound of the formula (I) of the present invention include the following compounds. 3- (2-
Cyanoethyl) -2-cyanoiminotetrahydro-1,
3-thiazine, 3- (2-cyanoethyl) -2-cyanoiminothiazolidine, 3- (2-cyanoethyl) -2-
Nitroiminotetrahydro-1,3-thiazine, 3-
(2-cyanoethyl) -2-cyanoiminooxazolidine, 3- (2-cyanoethyl) -2-cyanoiminotetrahydro-1,3-oxazine, 1- (2-cyanoethyl) -2-nitroimino-1,2-dihydropyridine,
1- (2-cyanoethyl) -2-cyanoimino-1,2
-Dihydropyridine, 3- (2-cyanoethyl) -2-
Cyanoiminothiazolidine, 3- (3-cyanopropyl) -2-cyanoiminotetrahydro-1,3-thiazine, 1- (3-cyanopropyl) -2-nitroiminopyrrolidine, 1- (3-cyanopropyl) -2 -Nitroimino-1,2-dihydropyrimidine.

In the production method a), as raw materials, for example,
2-cyanoiminotetrahydro-1,3-thiazine,
When 3-chloropropionitrile is used, it is represented by the following reaction formula.

Embedded image

In the production method b), as a raw material, for example, 3
When-(2-hydroxyethyl) aminopropionitrile and dimethyl N-cyanodithioiminocarbonate are used, they are represented by the following reaction formula.

Embedded image

In the above production method a), the raw material of the formula (I
The compounds of I) are based on the above definitions of A, X and Y. In formula (II), A, X and Y preferably have the same meanings as defined above. The compound of the formula (II) is already known in the literature in the field of organic chemistry, and specific examples thereof include 2-cyanoiminotetrahydro-1,3-thiazine and 2-cyanoiminotetrahydro-1,3-. Oxazine, 2-nitroiminotetrahydro-1,3-thiazine, 2-nitroiminothiazolidine,
Examples thereof include 2-cyanoiminothiazolidine, 2-cyanoiminopyrrolidine, 2-cyanoiminopiperidine, 2-nitroiminopyrrolidine, 2-nitroiminopiperidine, 2-cyanoaminothiazoline, and 2-nitroaminopyridine.

Similarly, the compound of the formula (III) which is a raw material of the production method a) means a compound based on the above definitions of R and Hal. In formula (III), R preferably has the same meaning as defined above, and Hal preferably represents chlorine or bromine. The compound of formula (III) is well known in the field of organic chemistry, and specific examples thereof include:
2-chloroacetonitrile, 2-chloropropionitrile, etc. can be illustrated.

In the above production method b), the raw material of the formula (I
The compound V) means the compound based on the definitions of R, A ¹ and X ¹ above. In the formula (IV), R, for the A ¹ and X ¹ is preferably R, shows a preferred definition synonymous with the, for A ¹ and X ^1, respectively, in the preferred definitions of the A and X The same definition and definition are shown. Compounds of formula (IV) are described, for example, in J. Am. Chem.
Soc. (Journal of American Chemical Society), Volume 72, pp. 1814-1815, or J.P.
ham. Sci. (Journal of Pharmaceutical Sciences), Volume 59, pages 1350 to 1352 and the like. Specific examples thereof include 3- (2-mercaptoethyl) aminopropionitrile and 3- (2-hydroxyethyl) aminopropionitrile. In the production method b), the compound of the formula (V) which is also a raw material is a known compound,
Specific examples thereof include dimethyl N-cyanoiminodithiocarbonate, nitroguanidine, and N-nitro S-methylisothiourea.

In carrying out the process a) mentioned above, use may be made, as suitable diluent, of any inert solvent. Examples of such diluents are water; aliphatic, cycloaliphatic and aromatic hydrocarbons (which may optionally be chlorinated) such as hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, Methylene chloride, chloroform, carbon tetrachloride, ethylene chloride and trichloroethylene, chlorobenzene; other ethers such as diethyl ether, methyl ethyl ether, di-iso-propyl ether, dibutyl ether, propylene oxide, dioxane,
Tetrahydrofuran; Nitriles such as acetonitrile, propionitrile, acrylonitrile; Alcohols such as methanol, ethanol, iso-propanol, butanol, ethylene glycol; Acid amides such as dimethylformamide, dimethylacetamide; Sulfone, sulfoxides such as dimethyl sulfoxide , Sulfolane; and bases, for example, hydrides such as sodium hydride and potassium hydride, hydroxides and carbonates of alkali metals, and tertiary amines such as triethylamine.

The above-mentioned production method a) can be carried out within a wide temperature range, and is generally about 0 ° C to about 100 ° C.
It can be preferably carried out at a temperature between about 10 ° C and about 80 ° C. Further, the reaction is preferably carried out under normal pressure, but it may be carried out under pressure or reduced pressure. Manufacturing method a)
In carrying out, for example, compound 1 of formula (II)
Sodium hydride as a base for mol
About 1.1 times to 1.2 times the molar amount, the compound of the formula (III) is equimolar amount to about 1.2 times the molar amount, preferably the equimolar amount to about 1.
The desired compound can be obtained by reacting a 1-fold molar amount in an inert solvent such as dimethylformamide.

In carrying out the process b) above, suitable inert diluents include all inert solvents similar to those exemplified in the process a). The above-mentioned production method b) can be carried out within a wide temperature range, for example, about 0
C. to about 100.degree. C., preferably about 30.degree. C. to about 80.degree. Further, the reaction is preferably carried out under normal pressure, but it may be carried out under pressure or reduced pressure. In carrying out the above-mentioned production method b), for example, 1 mol of the compound of the formula (IV) is equimolar to about 1.2 times the molar amount of the compound of the formula (V), preferably the equimolar amount to about 1.
A 1-fold molar amount, an inert solvent such as an alcohol (eg,
The desired novel compound can be obtained by reacting in a (methanol, ethanol) solvent until generation of mercaptan and / or ammonia stops.

The compounds of formula (I) according to the invention exhibit a strong insecticidal action. Therefore, they can be used as pesticides. Then, the active compound of formula (I) of the present invention exerts a proper controlling effect against harmful insects without giving phytotoxicity to cultivated plants. In addition, the compounds of the present invention can be used for controlling a wide variety of pests, harmful sucking insects, biting insects and other plant parasitic pests, storage pests, sanitary pests, and the like, and can be applied for their eradication.

Examples of such pests include the following pests. As insects, pests of the order Coleoptera, such as the weevil Weevil (Callosobruchus chine)
nsis), stag beetle (Sitophilus zeamais), stag beetle (Tribolium castaneum), stag beetle (Epilachna vigintioctomaculata), flying squirrel (Agriotes fuscicollis), stag beetle (Anomala rufocup)
(Leptinotarsa decemlineata), Diablotheca (Diab
rotica spp.), pine wood chafer (Monochamus alt)
ernatus), rice weevil (Lissorhoptrus oryzophi)
lus), flat beetle (Lyctus bruneus); Lepidoptera, such as gypsy moth (Lymantria dispar), plum bug (Malacosoma neustria), caterpillar (Pieris rapa)
e), Spodoptera litura, Spodoptera litura (M)
amestrabrassicae), Nikameichu (Chilo suppressor
alis), Awanomega (Pyrausta nubilalis), Aedes aegypti (Ephestia cautella), Scutellaria palustris
(Adoxophyes orana), Codling moth (Carpocapsa pomone
lla), Kaburagaga (Agrotis fucosa), Honey honey (G)
alleria mellonella), diamondback moth (Plutella maculipenni)
s), citrus fruit moth (Phyllocnistis citrella);

Hemiptera, for example leafhopper (Neph)
otettix cincticeps), brown planthopper (Nilaparvatal)
ugens), scale insect (Pseudococcus comsto)
cki), the scale insect (Unaspis yanonensis),
Green peach aphid (Myzus persicae), apple aphid (Aphis pomi), cotton aphid (Aphis gossypi)
i), Rhopalosiphum pseudob
rassicas), nasi gumbai (Stephanitis nashi), green bug (Nezara spp.), bed bug (Cimex lectular)
ius), Whitefly (Trialeurodes vaporarioru)
m), Psyllidae (Psylla spp.); Orthoptera, for example, German cockroach (Blatella germanica), American cockroach
(Periplaneta americana), Kera (Gryllotalpa africa
na), grasshopper (Locusta migratoria migratoriodes);
Isoptera, for example, the termite (Deucotermes sper)
atus), house termite (Coptotermes formosanus); Diptera, such as house flies (Musca domestica), Aedes aegypti, and fly fly (Hylemia platur)
a), Culex pipiens, Culex pipiens
opheles slnensis), Culex tritae
niorhynchus), and the like.

Furthermore, in the field of veterinary medicine, the novel compounds of the present invention are effective for use against various harmful animal parasites (internal and ectoparasites) such as insects and helminths. . Examples of such animal parasites include the following pests. Examples of insects include the fruit fly (Gastrophilus spp.), The sand fly (Stomoxys spp.), The lice (Trichodectes spp.),
Common tortoise (Rhodnius spp.), Dog flea (Ctenocephalide)
s canis) and the like. In the present invention, a substance having an insecticidal action against insects including all of them may be called an insecticide.

The active compounds of formula (I) according to the invention can be in the usual pharmaceutical forms. And as such a form,
Liquids, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active compound infiltrations-natural and synthetic, microcapsules, seed coatings, formulations with a combustion device (e.g. as a combustion device, Fumigation and fumes cartridges, cans and coils), and ULV (cold mist, warm mist)
Can be mentioned. These formulations can be manufactured by a known method. Such a method comprises, for example, applying the active compound to a developing agent, ie a liquid diluent; a liquefied gas diluent;
Solid diluents or carriers, optionally surfactants, ie emulsifiers and / or dispersants and / or foam formers, can be used by mixing. When water is used as the developing agent, for example, organic solvents can also be used as auxiliary solvents.

Examples of liquid diluents or carriers are, for example, aromatic hydrocarbons (eg xylene, toluene,
Alkylnaphthalene etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg chlorobenzenes, ethylene chloride, methylene chloride etc.), aliphatic hydrocarbons [eg cyclohexane etc., paraffins (eg mineral oil fractions Etc.]], alcohols (eg, butanol, glycol and their ethers, esters, etc.), ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), strong polar solvents (eg, dimethylformamide, dimethyl sulfoxide, etc.) )
And we can mention water. The liquefied gas diluent or carrier is a gas at normal temperature and pressure, and examples thereof include butane, propane, nitrogen gas, carbon dioxide, and aerosol propellants such as halogenated hydrocarbons. . As the solid diluent, soil natural minerals (for example, kaolin, clay, talc, chalk, quartz, attapal guide, montmorillonite, diatomaceous earth, etc.), soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.) Can be mentioned. Solid carriers for granules include crushed and fractionated rock (eg,
Calcite, marble, pumice, sepiolite, dolomite, etc., synthetic particles of inorganic and organic powders, and fine particles or organic substances (eg sawdust, coconut fruit, corn cobs and tobacco stems, etc.) ) Can be mentioned.

Examples of the emulsifier and / or foaming agent include nonionic and anionic emulsifiers [eg polyoxyethylene fatty acid ester, polyoxyethylene fatty acid alcohol ether (eg alkylaryl polyglycol ether, alkyl sulfonate, alkyl sulfate). , Aryl sulfonates, etc.)], and albumin hydrolysis products. Dispersants include, for example, lignin sulfite waste liquor and methylcellulose.
Adhesives can also be used in the formulation (powder, granules, emulsions), such adhesives including carboxymethylcellulose and natural and synthetic polymers (eg gum arabic, polyvinyl alcohol and polyvinyl acetate). You can A colorant can also be used, and as such a colorant, an inorganic pigment (for example, iron oxide,
Titanium oxide and Prussian blue), and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes and also trace elements such as their salts of iron, manganese, boron, copper, cobalt, molybdenum, zinc. You can

The preparation contains, for example, 0.1% of the active ingredient.
˜95 wt%, preferably 0.5 to 90 wt%. The formula (I) active compounds of the present invention are in their commercially useful formulations and in the use forms prepared by these formulations other active compounds such as insecticides, poison baits, fungicides, acaricides, It can also be used as a mixture with a sentinicide, a fungicide, a growth regulator or a herbicide. Here, examples of the insecticide include organic phosphorus agents, carbamate agents, carboxylate agents, chlorinated hydrocarbon agents, and insecticidal substances produced by microorganisms. Furthermore, the active compounds of formula (I) according to the invention can also be used as admixtures with synergists,
Examples of such formulations and use forms include those that are commercially useful. The synergist is a compound which amplifies the action of the active compound, which need not be active in and of itself. The content of the formula (I) active compounds of the invention in the commercially useful use forms can be varied within wide limits. The use concentration of the active compound of formula (I) of the present invention is, for example, 0.00
00001-100% by weight, preferably 0.00011-
It is 1% by weight. The compound of formula (I) of the present invention can be used by a usual method adapted to the use form. When used in hygiene pests, pests on stored matter, the active compounds are distinguished by a good stability against alkali on lime substances, as well as by a good residual effect in wood and soil.

[0027]

BEST MODE FOR CARRYING OUT THE INVENTION Next, the contents of the present invention will be described in detail with reference to Examples, but the present invention should not be limited thereto.

Manufacturing Example: Example 1

Embedded image 2-cyanoiminotetrahydro-1,3-thiazine (1.4 g), 3-chloropropionitrile (0.9
g), potassium carbonate (1.4 g), acetonitrile (3
The mixture (0 ml) is refluxed for 4 hours with stirring. After the reaction, acetonitrile is distilled off under reduced pressure, dichloromethane is added to the residue, and the mixture is washed with water and 1% sodium hydroxide aqueous solution. If the dichloromethane layer is dried and then concentrated, the target substance becomes crystals and precipitates. Therefore, the target substance is filtered, washed with a small amount of ether and dried to obtain the target 3- (2-cyanoethyl) -2-cyanoiminotetrahydro-1,3. -Thiazine (1.2
g) is obtained. mp. 85-88 ° C

Embodiment 2

[Chemical 12] 2-Nitroaminopyridine (2.8 g), 3-chloropropionitrile (1.8 g), triethylamine (2.
2g), while stirring a solution of ethanol (50 ml),
Reflux for 3 hours. After ethanol is distilled off under reduced pressure, water is added to the residue and the mixture is extracted with dichloromethane. The dichloromethane layer is washed with water and 1% hydrochloric acid and then dried. After concentration of dichloromethane, the residue was purified by silica gel column chromatography to obtain the desired 1- (2-cyanoethyl) -2.
-Nitroimino-1,2-dihydropyridine (0.8
g) is obtained. mp. 136-140 ° C

Example 3

Embedded image A solution of 3- (2-hydroxyethyl) aminopropionitrile (1.1 g) and dimethyl N-cyanodithioiminocarbonate (1.5 g) in ethanol (25 ml) was added 3 times.
Reflux for days. Then, depressurize the ethanol to about 2/3.
When concentrated and allowed to cool, the target substance precipitates as crystals, so the target 3- (2-cyanoethyl) -2-cyanoiminooxazolidine (0.7 g) is obtained by filtering, washing with a small amount of ethanol and drying. . mp. 100 ~
102 ° C

The compounds of formula (I) of the present invention produced by the same method as in Examples 1 to 3 are shown in Table 1 below together with the compounds of Examples 1 to 3.

[0032]

[Table 1]

[0033]

[Table 2]

[0034]

[Table 3]

Biological test example: Comparative compound

Embedded image

Example 4 (Biological test) Test against organophosphorus-drug-resistant leafhoppers Preparation of reagent solution Solvent: 3 parts by weight of xylol Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether To make a suitable active compound formulation 1 part by weight of the active compound was mixed with the above amount of solvent containing the above amount of emulsifier and the mixture was diluted with water to the given concentration. Test method: To a rice plant having a plant height of about 10 cm planted in a pot having a diameter of 12 cm, 10 ml of a diluted solution of the active compound prepared as above at a predetermined concentration was sprayed per pot. After spraying the chemical solution, cover it with a wire net with a diameter of 7 cm and a height of 14 cm. Release 30 female adults of the leafhopper leafhopper, which is a strain that is resistant to organophosphorus agents, and place it in a temperature-controlled room for 2 days. Insect kill rates were calculated. The results are shown in Table 2 with a representative example.

[0037]

[Table 4]

Example 5 Test for Organic Phosphorus Agent and Carbamate-Resistant Green Aphid Test Method: Organophosphorus agent raised in eggplant seedlings (genuine long eggplant) having a height of about 20 cm planted in a clay pot having a diameter of 15 cm, and About 20 peach aphids resistant to carbamate per seedling
0 head was inoculated, and one day after the inoculation, a sufficient amount of a diluted solution of the active compound in water prepared in the same manner as in Example 4 was sprayed using a spray gun. After spraying, it was left in a greenhouse at 28 ° C., and 24 hours after spraying, the insecticidal rate was calculated. The test was repeated twice. Table 3 shows the results.

[0039]

[Table 5]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location A01N 43/76 A01N 43/76 43/78 43/78 F 43/86 102 43/86 102 C07D 211 / 72 C07D 211/72 211/84 211/84 213/76 213/76 233/88 233/88 239/18 239/18 239/22 239/22 263/28 263/28 263/48 263/48 265 / 08 265/08 277/18 277/18 277/38 277/38 279/06 279/06 (72) Inventor Yumi Hattori 598 Obiki-cho, Hachioji-shi, Tokyo (72) Inventor Katsuhiko Shibuya Namiki-machi, Hachioji-shi, Tokyo 39-15

Claims (3)

[Claims] 1. The formula: In the formula, R represents cyanoalkyl having alkyl having 1 to 5 carbons, and A is a divalent group of a saturated hydrocarbon chain having 2 to 3 carbons which may be alkyl substituted, or alkyl substituted. Optionally represents a divalent or trivalent group of an unsaturated hydrocarbon chain having 2 to 3 carbon atoms, the bond “→” between A and X is monovalent or divalent, and X is N
H, N, O, S, CH or CH ₂ is shown, and Y is nitro, and when X is NH, A is an optionally substituted unsaturated hydrocarbon having 2 to 3 carbon atoms. Represents a divalent group of a chain, and when X represents N, A represents a trivalent group of an unsaturated hydrocarbon chain having 2 to 3 carbon atoms which may be alkyl-substituted, and A and X Is a cyanoalkyl-heterocyclic compound represented by. 2. R represents cyanoalkyl having alkyl of 1 to 3 carbons, and A is a divalent group of a saturated hydrocarbon chain of 2 to 3 carbons which may be methyl substituted, or methyl substituted. Optionally represents a divalent or trivalent group of an unsaturated hydrocarbon chain having 2 to 3 carbon atoms, the bond “→” between A and X is monovalent or divalent, and X is N
When H, N, O, S, CH or CH ₂ is shown and Y is nitro, and X is NH, A is an optionally substituted unsaturated hydrocarbon having 2 to 3 carbon atoms. A divalent group in the chain, and when X represents N, A is 3 of an unsaturated hydrocarbon chain having 2 to 3 carbon atoms which may be methyl-substituted.
The compound according to claim 1, which represents a valent group. 3. The formula: In the formula, R represents cyanoalkyl having alkyl having 1 to 5 carbons, and A is a divalent group of a saturated hydrocarbon chain having 2 to 3 carbons which may be alkyl substituted, or alkyl substituted. Optionally represents a divalent or trivalent group of an unsaturated hydrocarbon chain having 2 to 3 carbon atoms, the bond “→” between A and X is monovalent or divalent, and X is N
H, N, O, S, CH or CH ₂ is shown, and Y is nitro, and when X is NH, A is an optionally substituted unsaturated hydrocarbon having 2 to 3 carbon atoms. Represents a divalent group of a chain, and when X represents N, A represents a trivalent group of an unsaturated hydrocarbon chain having 2 to 3 carbon atoms which may be alkyl-substituted, and A and X The pesticide containing a cyanoalkyl-heterocyclic compound represented by, as the active ingredient, has a bond “→” of 2 as the active ingredient.