JP2715583B2 - Hydrazone compounds and insecticides containing the same as active ingredients - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a novel hydrazone compound and an insecticide containing the same as an active ingredient.

<Prior Art> Compounds having a structure similar to the hydrazone compound of the present invention are disclosed in JP-A-54-122261 and JP-A-56-4545.
It is described in Japanese Patent Publication No. 2 and the like. However, these compounds are not necessarily sufficient in terms of insecticidal efficacy.

<Means for Solving the Problems> In view of such circumstances, the present inventors have conducted various studies in order to develop compounds having excellent insecticidal efficacy.
The present inventors have found that a novel hydrazone compound represented by the following general formula [I] has an excellent insecticidal effect, and have reached the present invention.

That is, the present invention provides a compound represented by the general formula [I]: [Wherein, R ¹ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group which may be substituted with an alkyl group having 3 to 8 carbon atoms, an alkenyl group having 3 to 8 carbon atoms, An alkynyl group having 3 to 8 carbon atoms, an optionally substituted aralkyl group having 7 to 10 carbon atoms, a phenyl group which may be substituted, or a phenoxyalkyl having 8 to 10 carbon atoms which may be substituted; Represents a group. R ² is an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group which may be substituted by an alkyl group having 3 to 8 carbon atoms, an alkenyl group having 3 to 8 carbon atoms, an alkynyl group having 3 to 8 carbon atoms Or an optionally substituted aralkyl group having 7 to 10 carbon atoms, a phenyl group which may be substituted or an optionally substituted phenoxyalkyl group having 8 to 10 carbon atoms. Where R ¹ and
R ² does not simultaneously represent a methyl group. Also, R ¹
R ² may form a ring by bonding at the terminal, and the ring may contain an oxygen atom, a sulfur atom or a nitrogen atom. ] (Hereinafter, referred to as the compound of the present invention) and an insecticide containing the same as an active ingredient.

The compound of the present invention is included in the general formula described in JP-A-56-45452, but there is no specific description of the compound of the present invention, and it is clear from later test examples. As described above, the compounds of the present invention have extremely high insecticidal activity as compared with the related compounds described in the publication.

In the compound of the present invention represented by the general formula [I], the alkyl group having 1 to 8 carbon atoms represented by R ¹ and R ² is, for example, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, -Butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, iso-pentyl group, sec-pentyl group, 1-ethylpropyl group, neo-pentyl group, n-hexyl group, The cycloalkyl group which may be substituted with an alkyl group having 3 to 8 carbon atoms, such as an n-heptyl group and an n-octyl group, is, for example, a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group , 2-methylcyclopropyl, 1-methylcyclobutyl, cyclopentyl, cyclohexyl, 2
-Methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, cycloheptyl group,
Examples thereof include a 4-ethylcyclohexyl group and a cyclooctyl group, and the alkenyl group having 3 to 8 carbon atoms includes, for example, a 2-propynyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 2-methyl-2-propenyl group. Butenyl group, 3-butenyl group, 2-methyl-2-butenyl group, 3-methyl-2-butenyl group, 2-pentenyl group, 3-pentenyl group, 4-
Pentenyl group, 5-hexenyl group, 2-hexenyl group,
An alkynyl group having 3 to 8 carbon atoms such as a 2-octenyl group and the like means, for example, a 2-propynyl group, a 1-methyl-2-
Propynyl group, 1,1-dimethyl-2-propynyl group, 2
-Butynyl group, 2-pentynyl group, 2-hexynyl group,
2-Heptynyl group, 2-octynyl group and the like, and the aralkyl group having 7 to 10 carbon atoms which may be substituted,
For example, benzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 4-chlorobenzyl, 4-bromobenzyl, 4-methylbenzyl, 3-methylbenzyl, 4-ethylbenzyl Group, 3,4-dimethylbenzyl group, 3,4-dichlorobenzyl group, 4-iso-propylbenzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 4-methylthiobenzyl group, 4-cyanobenzyl group, 2-phenylethyl group, 2- (4-chlorophenyl) ethyl group, 2- (4-
Tolyl) ethyl group, 2- (4-bromophenyl) ethyl group, 3-phenylpropyl group, 1-phenylethyl group,
A phenyl group which may be substituted, for example, a phenyl group, a 2-tolyl group,
3-tolyl group, 4-tolyl group, 2-fluorophenyl group, 4-fluorophenyl group, 4-chlorophenyl group,
4-bromophenyl group, 4-trifluoromethylphenyl group, 4-methoxyphenyl group, 4-ethoxyphenyl group, 4-methylthiophenyl group, 4-benzyloxyphenyl group, 4-phenoxyphenyl group, etc. Examples of the optionally substituted phenoxyalkyl group having 8 to 10 groups include a 2-phenoxyethyl group and a 2- (4-
A fluorophenoxy) ethyl group, a 2- (4-chlorophenoxy) ethyl group, a 2- (2-fluorophenoxy) ethyl group, and a 2- (2,4-dichlorophenoxy) ethyl group.

The pests against which the compound of the present invention is effective include, for example, Japanese moth moth, Japanese mulberry, Japanese moth moth, armyworm, lingua,
Lepidoptera such as cabbage butterflies, locusts and moths, diptera such as Culex pipiens, Aedes aegypti, anopheles, houseflies, etc .; , Northern corn root worms, Coleoptera such as scarab beetles, Hymenoptera such as brown ants, black ants, etc., other Panoptera, Isoptera,
Orthoptera and the like, and are also effective against pests that have developed resistance to existing insecticides.

The compound of the present invention exhibits high insecticidal activity against the above-mentioned pests by direct contact with the insect body, but expresses more excellent efficacy when fed orally.

Therefore, the compound of the present invention is a poisonous insecticide (poison bait for controlling pests) against lepidopteran pests, dipteran pests, lepidopteran pests, coleoptera pests, hymenoptera pests and other various pests. Exerts particularly good efficacy.

Typical production methods of the compound of the present invention include, for example, the following methods.

Production method A Formula [II] And a compound represented by the general formula (III) [Wherein, R ¹ and R ² represent the same meaning as described above. By reacting with an amine compound represented by
A method for producing the compound of the present invention represented by the general formula [I].

Production method B Formula [IV] A method for producing the compound of the present invention represented by the general formula [I] by reacting the compound represented by the general formula [III] with the amine compound represented by the general formula [III].

In the production methods A and B, a solvent is not necessarily required for production, but when a solvent is used, for example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, o-dichlorobenzene, and pyridine , Pyridines such as picoline, chloroform, carbon tetrachloride, 1,2
-Dichloroethane, 1,1,1-trichloroethane, tetrachloroethylene, halogenated hydrocarbons such as trichloroethylene, n-hexane, aliphatic hydrocarbons such as n-heptane, alicyclic hydrocarbons such as cyclohexane, water and the like or These mixed solvents are used, and the amine compound represented by the general formula [III] is usually used in a proportion of 1 to 100 mol per 1 mol of the compound represented by the formula [II]. Further, based on 1 mol of the compound represented by the formula [IV],
The amine compound represented by the general formula [III] is used in a proportion of 1 to 100 mol. The reaction temperature is usually -20 to 200 ° C,
It is preferably 0 to 100 ° C, and the reaction time is usually 5 minutes to 100 ° C.
Time. After completion of the reaction, the desired compound of the present invention can be obtained by performing ordinary post-treatment.

The compounds represented by the formulas (II) and (IV) are novel compounds, and the compound represented by the formula (II) is, for example, a compound represented by the formula (V) Can be produced by reacting a compound represented by the formula with phosphorus pentachloride, the compound represented by the formula (IV) is
For example, it can be produced by reacting a compound represented by the formula [V] with phosphorus oxychloride.

In these production methods, a solvent is not necessarily required, but when a solvent is used, for example, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, o-dichlorobenzene, chloroform, carbon tetrachloride, ,
Halogenated hydrocarbons such as 2-dichloroethane, 1,1,1-trichloroethane, tetrachloroethylene and trichloroethylene; aliphatic hydrocarbons such as n-hexane and n-heptane; alicyclic hydrocarbons such as cyclohexane and the like; A mixed solvent is used.

When a compound represented by the formula [V] is reacted with phosphorus pentachloride to produce a compound represented by the formula [II], usually, 1 mol of the compound represented by the formula [V] is used, and It is used in a proportion of 1 to 5 mol. The reaction temperature is usually room temperature to 250 ° C, preferably 100 to 180 ° C, and the reaction time is
Usually 5 minutes to 100 hours.

When a compound represented by the formula [V] is reacted with phosphorus oxychloride to produce a compound represented by the formula [IV], the oxychloride is usually added to 1 mol of the compound represented by the formula [V]. Phosphorus is used in a proportion of 1 to 5 mol. The reaction temperature is generally 0 to 250 ° C, preferably 10 to 180 ° C, and the reaction time is generally 5 minutes to 100 hours.

After completion of the reaction, the compound represented by the formula [II] or [IV] can be obtained by performing ordinary post-treatment.

Formula (II) or (IV) produced by these methods
Can also be used for the reaction of Production Method A or B, respectively, without isolation and purification.

The compound represented by the formula [V] is a known compound and can be produced, for example, by the method described in JP-A-56-45452.

The compound of the present invention has two types of geometric isomers depending on the configuration of the double bond of the hydrazone, including both geometric isomers and a mixture of the two geometric isomers, each of which is an insecticide. It can be used as an agent.

When the compound of the present invention is used as an active ingredient of an insecticide, it may be used as it is without adding any other components, but it is usually mixed with a solid carrier, a liquid carrier, a gaseous carrier, a bait, and the like. If necessary, add surfactants and other formulation auxiliaries, oils, emulsions, wettable powders, flowables, granules, powders, aerosols, aerosols (fogging etc.),
It is used as a poison bait.

In these preparations, the compound of the present invention as an active ingredient,
Usually, it is contained in an amount of 0.01% to 95% by weight.

Examples of solid carriers used in the formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide,
Bentonite, fubasami clay, acid clay, etc.), talc, ceramics, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc.),
Fine powders or granular materials such as chemical fertilizers (ammonium sulfate, phosphorous ammonium, ammonium nitrate, urea, salt ammonium, etc.) are listed.
For example, water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.),
Aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, kerosene, light oil, etc.), alicyclic hydrocarbons (cyclohexane, etc.), esters (ethyl acetate, Butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.),
Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide, vegetable oils such as soybean oil, cottonseed oil and the like. Examples of the gaseous carrier, that is, the propellant include Freon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas and the like.

Examples of the surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl sulfates, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphates, and naphthalene. Examples include anionic surfactants such as sulfonic acid formalin condensate, and nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester.

Examples of pharmaceutical auxiliaries such as fixatives and dispersants include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (polyvinyl alcohol) , Polyvinylpyrrolidone, polyacrylic acids and the like), and examples of the stabilizer include PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), and BHA (2-tert-butylphenol). -Butyl-
A mixture of 4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, surfactant, fatty acid or ester thereof, and the like.

As a bait bait, for example, cereal flour, vegetable flour, starch, vegetable essential oil, sugar, crystalline cellulose, fish meal, chicken eggs, dairy products, proteins, fatty acid sugar, bait components, dibutylhydroxytoluene, butylhydroxyanisole, nordihydro Antioxidants such as guaiaretic acid, preservatives such as dehydroacetic acid, ingestion inhibitors such as pepper powder, cheese flavor,
Examples include attracting flavors such as onion flavors and peanut oil.

The preparation thus obtained is used as it is or diluted with water or the like. Also, other insecticides, nematicides,
It can be used with or without mixing with acaricides, soil pesticides, pesticides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil improvers, and the like.

When the compound of the present invention is used as an agricultural pesticide, the application rate is usually 5 g to 500 g per 10 ares, an emulsion,
When using wettable powders, flowables, etc. diluted with water,
The application concentration is 1 ppm to 500 ppm, and granules, powders and the like are applied as they are without dilution. When used as an insecticide for epidemics, emulsions, wettable powders, flowables, etc. are diluted with water to 1 ppm to 500 ppm and applied, and oils,
Aerosols, aerosols and poison baits are applied as they are.

Hereinafter, the present invention will be described in more detail with reference to Production Examples, Formulation Examples, and Test Examples, but the present invention is not limited thereto.

 First, a production example will be described.

Production Example 1 4-Chloro-4'-trifluoromethylsulfonyloxybenzophenone-N '-(1-chloroethylidene)
A solution of 300 mg (0.68 mmol) of hydrazone in benzene (5 ml) was added at once at 5-10 ° C. while stirring vigorously with 5 ml of methylamine (40% aqueous solution). After stirring at room temperature for 2 hours, the mixture was diluted with 20 ml of benzene, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting oil was subjected to column chromatography using activated alumina,
260 mg of the present compound (1) was obtained as a yellow oil. ▲ n
^23.1 _D ▼ 1.5935 Production Example 2 4-chloro-4'-trifluoromethylsulfonyloxybenzophenone-N '-[1- (dichlorophosphonyloxy) ethylidene] hydrazone 300 mg (0.56 mmol)
Of toluene (5 ml) was vigorously stirred while 5 ml of ethylamine (70% aqueous solution) was added in one portion at 5-10 ° C. After stirring at room temperature for 15 hours, the same post-treatment as in Production Example 1 was performed to obtain 140 mg of the desired present compound (2) as a yellow oil. ▲ n ^22.9 _D ▼ 1.5929 Production Example 3 300 mg of 4-chloro-4′-trifluoromethylsulfonyloxybenzophenone-N′-acetylhydrazone
(0.71 mmol), 68 mg (0.78 mmol) of phosphorus pentachloride and p-
A mixture of 5 ml of xylene was heated to reflux under a nitrogen atmosphere for 10 hours. After the completion of the reaction, the mixture was cooled to 5 to 10 ° C., and 10 ml of N-methyl N-ethylamine (50% aqueous solution) was added thereto all at once with vigorous stirring. After stirring at room temperature for 3 hours, the same post-treatment as in Production Example 1 was carried out to obtain 265 mg of the desired present compound (10) as a yellow oil. ▲
n ^23.6 _D ▼ 1.5930 Production Example 4 300 mg of 4-chloro-4′-trifluoromethylsulfonyloxybenzophenone-N′-acetylhydrazone
(0.71 mmol), a mixture of 120 mg (0.78 mmol) of phosphorus oxychloride and 5 ml of toluene were heated to reflux under a nitrogen atmosphere for 10 hours. After the completion of the reaction, the mixture was cooled to 5 to 10 ° C., and 10 ml of diethylamine (50% aqueous solution) was added thereto at once with vigorous stirring. After stirring at room temperature for 5 hours, the same post-treatment as in Production Example 1 was performed to obtain 145 mg of the desired present compound (11) as a yellow oil. ▲ n ^24.0 _D ▼
1.5920 The compound of the present invention produced according to the above production method was converted to the following
Although shown in the table, of course, the present invention is not limited to these.

Next, formulation examples are shown. Parts are parts by weight, and the tested compounds of the present invention are indicated by the compound numbers in Table 1.

Formulation Example 1 Compounds (1) to (4), (6), (7), (9)
0.2 parts of each of (12) and (14), 2 parts of xylene, 2 parts of DMF and 95.8 parts of white kerosene are mixed to obtain respective oils.

Formulation Example 2 10 parts of each of compounds (1) to (30), 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene and 35 parts of DMF are mixed well to obtain each emulsion.

Formulation Example 3 20 parts of each of compounds (1) to (30), fenitrothion
10 parts, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 65 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain each wettable powder.

Formulation Example 4 1 part of each of compounds (1) to (30), carbaryl 2
Parts, 87 parts of kaolin clay and 10 parts of talc are thoroughly pulverized and mixed to obtain each powder.

Formulation Example 5 Compounds (1), (2), (4), (10), (11),
To 5 parts of each of (17), (18), and (20), 5 parts of synthetic hydrous silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite, and 55 parts of clay are added and sufficiently stirred and mixed. Then, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and air-dried to obtain 5% granules of each.

Formulation Example 6 Compounds (1) to (4), (6), (7), (9)
(12), 0.05 part of each (14), tetramethrin 0.2 part,
Resmethrin 0.05 parts, xylene 7 parts and deodorized kerosene 42.7
After mixing and dissolving the parts, filling into an aerosol container and attaching a valve part, 50 parts of a propellant (liquefied petroleum gas) is filled under pressure through the valve part to obtain each aerosol.

Formulation Example 7 Compounds (1), (2), (4), (10), (11),
20 parts of (17), (18) and (20) and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and then finely pulverized with a sand grinder (with a particle size of 3 μ or less). In this, xanthan gum 0.
Add 40 parts of an aqueous solution containing 05 parts and 0.1 part of aluminum magnesium silicate, and further add propylene glycol.
Add 10 parts and stir and mix to obtain each 20% suspension in water.

Formulation Example 8 Compounds (1) to (7), (9) to (12), (17),
One part of each of (18) and (22) was mixed with 3 parts of sesame oil, and 0.03 part of butylhydroxyanisole and 0.2 part of dehydroacetic acid were added thereto.
1 part, 10 parts of brown sugar, 30 parts of crystalline cellulose and 55.87 parts of potato starch were added, and after uniform mixing, 15 kg / cm
Apply the pressure of ² , press-mold into 1 tablet about 4g (diameter about 30mm),
Obtain each bait.

Next, test examples will be described. The tested compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison were:
It is shown by the compound symbol in Table 2.

Test Example 1 (Insecticidal test against Spodoptera litura) For 13 g of Spodoptera litura, 2 ml of a 200-fold diluted solution (500 ppm) of a test compound emulsion obtained in accordance with Formulation Example 2 with water was prepared in a polyethylene cup having a diameter of 11 cm. Soaked in artificial feed. Among them, the fourth cutworm of the cutworm, Spodoptera litura, 10
The heads were released and their mortality was determined 6 days later to determine the mortality (2 replicates). Table 3 shows the results.

Test Example 2 (Insecticidal test against Culex pipiens) An emulsion of the test compound obtained according to Formulation Example 2 was washed with water for 20 minutes.
The solution was diluted 0-fold, and 0.7 ml of the solution was added to 100 ml of ion-exchanged water (active ingredient concentration: 3.5 ppm). Twenty last larvae of Culex pipiens were released therein, and the mortality after one day was determined.

 The efficacy criteria were mortality a: 90% or more b: 10% or more and less than 90% c: less than 10%. Table 4 shows the results.

Test Example 3 (Insecticidal test against southern corn rootworm) 1 ml of a water dilution (50 ppm) of an emulsion of the test compound obtained according to Formulation Example 2 was placed on the bottom of a polyethylene cup having a diameter of 5.5 cm and the same size. After dripping on paper, 20-30 eggs of southern corn rootworm and one corn sprout were put in and capped. Eight days later, the larvae were examined for life and death, and the mortality was determined.

 The criterion for effectiveness was mortality a: 100% b: 90% or more and less than 100% c: less than 90%. Table 5 shows the results.

Test Example 4 (Insecticidal test on Kobumemeiga) 20 ml of a 20,000-fold diluted solution (5 ppm) of water of an emulsion of the test compound obtained in accordance with Formulation Example 2 was inoculated with about 20 larvae of the third to fourth instar larvae the day before. The rice was planted in plastic cups of 7 cm in diameter and 7 cm in depth. Three days after the drug treatment, the larvae were examined for survival or death (2 replicates).

 Table 6 shows the results.

Test Example 5 (Food Poisoning Test for German Cockroach) Acetone solution of a test compound was dropped into 0.5 g of solid feed for mouth and mouth (solid feed for breeding and breeding of Japanese CLEA CE-2), and 1% drug-treated feed (poisonous feed) ) Got. A small cup (diameter) is placed in a polyethylene container with a bottom diameter of 11 cm and a height of 10.5 cm.
3 cm), a drug-treated bait and an untreated bait, water, and a paper shelter were installed. Twenty adult German cockroaches (10 males and 10 females) were released into this container, and the mortality of the three days later was examined. The results are shown in Table 7.

Test Example 6 (Food Poisoning Test for Black Ants) 3 mg of the test compound was dissolved in 0.3 ml of acetone, and this solution was treated with a mixture of 2 g of skim milk powder and 1 g of granulated sugar, mixed uniformly, and then air-dried with acetone. 0.1% poison bait was obtained.
In a polyethylene cup (9.5 cm in diameter, 4.5 cm in height), 0.3 g of the poison bait put in a small plastic cup (2 cm in diameter, 1 cm in height) and a cotton ball (1 cm in diameter) soaked in water were placed. In this cup, 10 black ant adults were released and 11
Survival and death after days were investigated to determine the mortality. The results are shown in Table 8.

<Effects of the Invention> The compound of the present invention has excellent insecticidal activity against various pests such as lepidopteran pests, dipteran pests, coleoptera pests, lepidopteran pests, and hymenoptera pests, and especially is orally consumed. By being done
Shows even better insecticidal efficacy.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Yoko Torisu 4-2-1 Takashi Takarazuka-shi, Hyogo Prefecture Inside Sumitomo Chemical Co., Ltd. (72) Inventor Kenichi Mikitani 4-2-1 Takashi Takarazuka-shi Hyogo Prefecture Sumitomo Chemical Co., Ltd. (56) References JP-A-2-138246 (JP, A) JP-A-56-45452 (JP, A)

Claims (3)

(57) [Claims] (1) General formula [Wherein, R ¹ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group which may be substituted with an alkyl group having 3 to 8 carbon atoms, an alkenyl group having 3 to 8 carbon atoms, An alkynyl group having 3 to 8 carbon atoms, an optionally substituted aralkyl group having 7 to 10 carbon atoms, a phenyl group which may be substituted, or a phenoxyalkyl having 8 to 10 carbon atoms which may be substituted; Represents a group. R ² is an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group which may be substituted by an alkyl group having 3 to 8 carbon atoms, an alkenyl group having 3 to 8 carbon atoms, an alkynyl group having 3 to 8 carbon atoms Or an optionally substituted aralkyl group having 7 to 10 carbon atoms, a phenyl group which may be substituted or an optionally substituted phenoxyalkyl group having 8 to 10 carbon atoms. Where R ¹ and
R ² does not simultaneously represent a methyl group. Also, R ¹
R ² may form a ring by bonding at the terminal, and the ring may contain an oxygen atom, a sulfur atom or a nitrogen atom. ] The hydrazone type compound shown by these. 2. An insecticide comprising the hydrazone compound according to claim 1 as an active ingredient. 3. The insecticide according to claim 2, wherein the insecticide is a poisonous insecticide.