JPH0374356A - Hydrazone based compound, production thereof and insecticide containing same compound as active ingredient - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (R<1> is H, 1-8C alkyl, 3-8C alkenyl, 3-8C alkynyl, phenyl, etc.; R<2> is 1-8C alkyl, 3-8C alkenyl, 3-8C alkynyl, phenyl, etc.; R<1> may combine with R<2> to form a ring). USE:An insecticide. The compound expressed by formula I has excellent insecticidal effects against various kind of insect pests of Lepidoptera, Dileoptera, Coleoptera, Dictyoptera, Hymenoptera, etc., and exhibits further excellent insecticial effects by especially orally taking it in. PREPARATION:A compound expressed by formula II is reacted with an amine based compound expressed by formula III in the absence of a solvent or in a solvent such as benzene at -20 deg.C to 200 deg.C to provide the compound expressed by formula I. The compound expressed by formula II is also a new compound and obtained by reacting a compound expressed by formula IV with phosphorus pentachloride.

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a novel hydrazone compound, a method for producing the same, 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-5
It is described in Publication No. 6-45452 and the like. However, these compounds cannot necessarily be said to be sufficient in terms of insecticidal efficacy (6).

Means for Solving the Problems In view of the above circumstances, the present inventors have conducted various studies to develop a compound with excellent insecticidal efficacy, and as a result, have developed a novel compound represented by the following general formula (1). The present invention was based on the discovery that hydrazone compounds have excellent insecticidal efficacy.

That is, the present invention relates to the general formula [I) HB [wherein R1 is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms,
Alkyl group having 3 to 8 carbon atoms in total, optionally substituted cycloalkyl group, alkenyl group having 3 to 8 carbon atoms, alkynyl group having 3 to 8 carbon atoms, substituted unsubstituted group having 7 to 10 carbon atoms in total; represents an optionally substituted aralkyl group, an optionally substituted phenyl group, or an optionally substituted phenoxyalkyl group having 8 to 10 carbon atoms in total. R has 1 to 8 carbon atoms
an alkyl group having a total number of carbon atoms of 8 to 8, a cycloalkyl group which may be substituted with an alkyl group having a total number of carbon atoms of 8 to 8, an alkenyl group having a total of 8 to 8 carbon atoms, an alkynyl group having a total of 8 to 8 carbon atoms, a total number of carbon atoms of 7
~10 represents an optionally substituted aralkyl group, an optionally substituted phenyl group, or an optionally substituted phenoxyalkyl group having 8 to 10 carbon atoms in total. However, R'' and R2 do not represent a methyl group at the same time. In addition, R and R combine at the ends to form a ring, and the ring contains an oxygen atom, a sulfur atom, or a nitrogen atom. The present invention provides a hydrazone compound (hereinafter referred to as the compound of the present invention) represented by the following, a method for producing the same, 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 No. 56-45452, but there is no specific description of the compound of the present invention in the publication, and furthermore, it is clear from the test examples described later. As shown, the compound of the present invention has extremely high insecticidal efficacy compared to the related compounds described in the publication.

In the compound of the present invention represented by the general formula [■], the alkyl group having 1 to 8 carbon atoms represented by R1 and R2 is
For example, methyl group, ethyl group, n-propyl group, 1so
-propyl group, n-butyl group, 1so-butyl group, 5e
e-butyl group, tert-butyl group, n-pentyl group,
180-pentyl group, 8eC-pentyl group, 1-ethylpropyl group, neO-pentyl group, n-hexyl group, n
-hebutyl group, n-octyl group, etc., and the total number of carbon atoms is 8
The cycloalkyl group optionally substituted with an alkyl group of ~8 is, for example, a cyclopropyl group, a 1-methylcyclopropyl group, a cyclobutyl group, a 2-methylcyclopropyl group, a 1-methylcyclobutyl group, a cyclobengal group. , cyclohexyl group, 2-methylcyclohexyl group, 8
-Methylcyclohexyl group, 4-methylcyclohexyl group (
9) Alkenyl groups having 8 to 8 carbon atoms include, for example, 2-propynyl group, 1-methyl-2
-propenyl group, 2-methyl-2-propenyl group, 2-
Butenyl group, 3-butenyl group, 2-methyl-2-butenyl group, 8-methyl-2-butenyl group, 2-pentenyl group, 8-pentenyl group, 4-pentenyl group, 5-hexenyl group, 2- xenyl group, 2-octenyl group, etc.
Alkynyl groups having 8 to 8 carbon atoms include, for example, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 2-butynyl group, 2-pentynyl group, 2- The optionally substituted aralkyl group having 7 to 10 carbon atoms in total includes xynyl group, 2-hebutynyl group, 2-octenyl group, etc., and evabenzyl group, 2-octenyl group, etc.
-fluorobenzyl group, 3-fluorobenzyl group, 4-
Fluorobenzyl group, 4-chlorobenzyl group, 4-bromobenzyl group, 4-methylbenzyl group, 8-methylbe(
10) ndyl group, 4-ethylbenzyl group, 8,4-dimethylbenzyl group, 8,4-dichlorobenzyl group, 4-1so-
Propylbenzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 4-methylthiobenzyl group, 4-cyanobenzyl group, 2-phenylethyl group, 2-(4-chlorophenyl)ethyl group, 2-(4-) The phenyl group, which may be substituted, is such as lyl)ethyl group, 2-(4-bromophenyl)ethyl group, 8-phenylpropyl group, 1-phenylethyl group, 4-phenylbutyl group, etc.
For example, phenyl group, 2-tolyl group, 8-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-methylthio A phenyl group, a 4-benzyloxyphenyl group, a 4-phenoxyphenyl group, etc., and an optionally substituted phenoxyalkyl group having a total carbon number of 8 to 1o are, for example, a 2-phenoxyethyl group, a 2-(4 Fluorophenoxy)ethyl group, 2-(4-chlorophenoxy)ethyl! ,
2-(2-fluorophenoxy)ethyl M, 2-(2,
4-dichlorophenoxy)ethyl group, etc.

Examples of pests against which the compound of the present invention is effective include diamondback moth,
Nets of Lepidoptera such as Japanese and Japanese cockroaches, Knot borer moths, armyworms, Lepidopterans, cabbage moths, burrs, carp moths, Culex mosquitoes, Aedes aegypti, Anopheles mosquitoes, Striped mosquitoes, House flies and other Diptera, German cockroaches, black cockroaches, Japanese cockroaches, American cockroaches, etc. Ptera, Azuki weevils,
Southern corn rootworms, northern corn rootworms, coleopterans such as scarab beetles, Hymenoptera such as brown ants and black wood ants, their caterpillars, isoptera, orthoptera, etc., as well as existing insecticides. It is also effective against pests that have developed resistance.

The compound of the present invention exhibits high insecticidal efficacy against the above-mentioned insect pests when it comes into direct contact with the insect bodies, but exhibits even more excellent efficacy when ingested orally.

Therefore, the compound of the present invention can be used as a pre-meal insecticide (poison bait for pest control) against Lepidoptera pests, Diptera pests, Reticuloptera pests, Coleoptera pests, Hymenoptera pests, and various other pests.
1 Demonstrates particularly excellent efficacy.

Typical methods for producing the compounds of the present invention include, for example, the following methods.

Manufacturer: A compound represented by the formula (n) and the general formula [醊] [In the formula, R1 and R2 have the same meanings as above (13). ] By reacting with the amine compound shown in
A method for producing the compound of the present invention represented by general formula (1).

Production Method B A method for producing the compound of the present invention represented by formula (1) by reacting the compound represented by formula (W) with an amine compound represented by formula (W).

In manufacturing corporation and B, a solvent is not necessarily required during manufacturing, but when a solvent is used, for example, benzene, toluene, xylene, chlorobenzene, 0-
Aromatic hydrocarbons such as dichlorobenzene, (14) pyridines such as pyridine and picoline, halogenated hydrocarbons such as chloroform, carbon tetrachloride, If2-dichloroethane, 1,1,1-)dichloroethane, tetrachloroethylene, trichloroethylene, etc. [, aliphatic hydrocarbons such as n-hexane, n-hebutane, alicyclic hydrocarbons such as cyclohexane, water, etc., or a mixed solvent thereof are used, and the compound 1 represented by formula (n) is usually used. The amine compound represented by the general formula Cm) is used in an amount of 1 to 100 moles.

Further, the amine compound represented by the general formula (1) is used in a ratio of 1 to 100 moles per 1 mole of the compound represented by the formula (IV). The reaction temperature is usually -20 to 200
"C1 is preferably 0 to 100°C, and the reaction time is usually 5 minutes to 100 hours. After the reaction is completed, the desired compound of the present invention can be obtained by carrying out a usual post-treatment.

Compounds represented by formula (ff) and [■] are new compounds, and compounds represented by formula (If) are, for example, represented by formula (
V) It can be produced by reacting the compound represented by formula [■] with phosphorus pentachloride, and the compound represented by formula [■] is
For example, it can be produced by reacting a compound represented by formula M 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, 0-dichlorobenzene, chloroform, carbon tetrachloride, ．．
2-dichloroethane, 1,1.1-1-lichloroethane,
Halogenated hydrocarbons such as tetrachlorethylene and trichloroethylene, aliphatic hydrocarbons such as n-hexane and n-heptane, alicyclic hydrocarbons such as cyclohexane, or a mixed solvent thereof are used.

When producing a compound represented by formula (II) by reacting a compound represented by formula M with phosphorus pentachloride, the compound represented by formula [■
For 1 mole of the compound represented by
Used in molar proportions. The reaction temperature is usually room temperature to 25
The temperature is 0°C, preferably 100 to 180°C, and the reaction time is usually 5 minutes to 100 hours.

When the compound represented by the formula M is reacted with phosphorus oxychloride to produce the compound represented by the formula [■], usually 1 mole of the compound represented by the formula (V) is Phosphorus chloride is used in a proportion of 1 to 5 moles. The reaction temperature is usually 0 to 250°C, preferably 10 to 180°C.
°C, and the reaction time is usually 5 minutes to 100 hours.

After the reaction is completed, the formula (
11) or the compound represented by [■] can be obtained.

The compound represented by formula (n) or (b) produced by these methods can be used in the reaction of (17) Manufacturing Corporation or B, respectively, without isolation or purification.

The compound represented by 2M 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, and includes any of the geometric isomers and a mixture of the two types of geometric isomers,
Each of them can be used as an insecticide.

When using the compound of the present invention as an active ingredient of an insecticide,
You can use it as is without adding any other ingredients, but
Usually, it is mixed with a solid carrier, liquid carrier, gaseous carrier, feed, etc., and if necessary, surfactants and other formulation auxiliaries are added to form oils, emulsions, wettable powders, flowables, and granules. , powder, aerosol, smoke (fogging, etc.), poison bait, etc.

These preparations usually contain the compound of the present invention as an active ingredient! Contains 0.01% to 95% (18).

Solid carriers used in formulation include, for example, clays (kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (sericite, quartz,
Sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphorus, ammonium nitrate, urea, ammonium chloride, etc.), and other fine powders or granules.As liquid carriers, for example, water, alcohol, etc. (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.) 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, etc., and gaseous carriers, that is, propellants, include:
Examples include chlorofluorocarbon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas, and the like.

Examples of surfactants used for emulsification, dispersion, wetting, etc. include alkyl sulfate ester salts, alkyl (aryl) sulfonates, dialkyl sulfosuccinates,
Anionic surfactants such as polyoxyethylene alkylaryl ether phosphate ester salts, naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters Nonionic surfactants such as

Examples of formulation aids such as fixing agents and dispersants include casein, gelatin, polysaccharides (starch powder, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (polyvinyl alcohol, etc.) , polyvinylpyrrolidone, polyacrylic acids, etc.), and examples of stabilizers include PAP (
acidic isopropyl phosphate), BI(T(2,6-sheet t
ert-butyl-4-methylphenol), BHA (
2-tert-phthyl-4-methoxyphenol and 8-
(mixtures with teri-butyl-4-methoxyphenol), vegetable oils, mineral oils, surfactants, fatty acids or esters thereof, and the like.

Poison bait base materials include grain grains, plant flour, starch, vegetable essential oils, sugar, crystalline cellulose, fish meal, chicken eggs, dairy products, proteins, bait ingredients such as fatty acids, dibutylhydroxytoluene, butylhydroxyanisole, nordihydro Antioxidants such as guaiaretic acid, preservatives such as dehydroacetic acid, agents to prevent accidental ingestion such as chili pepper powder, cheese flavor (2
1) Attractive flavoring agents such as onion flavoring agents, onion flavoring agents, and peanut oil.

The preparation thus obtained is used as it is or diluted with water or the like. It may also be mixed with other insecticides, nematicides, acaricides, soil*pest control agents, pest control agents, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, etc. They can be used simultaneously or without mixing.

When the compound of the present invention is used as an agricultural insecticide, the application rate is usually 5F to 500F per 10 ares,
When emulsions, wettable powders, flowables, etc. are diluted with water and used, the applied concentration is tppm to 500 ppm, and granules, powders, etc. are applied as they are without any dilution. In addition, when used as an insecticide for epidemic prevention, emulsions, wettable powders, flowable agents, etc. should be used at a concentration of tppm to 500 in water.
I) Dilute to 1) m and apply. For oils, aerosols, fogs, and poison baits, apply as is.

The present invention (22) will be explained in more detail below using production examples, formulation examples, and test examples, but the present invention is not limited thereto.

First, let's look at the manufacturing side.

Production side 1 A solution of 4-chloro-4'-trifluoromethylsulfonyloxybenzophenone-N-(1-chloroethylidene)hydrazone 800m (0,687y+tno1) in benzene (5m/) was added to it while stirring vigorously. 10
At °C 5 m/m of methylamine (40% aqueous solution) was added in one portion. After stirring at room temperature for 2 hours, benzene 20m/! The mixture was diluted with water, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained oil was subjected to column chromatography using activated alumina to obtain the present compound (1) 260 fn9 as a yellow oil. n28” 1.
5985 Production side 2 4-chloro-4-trifluoromethylsulfonyloxybenzophenone-N'-(1-(dichlorophosphonyloxy)ethylidene)hydrazone 800IF (0.56m
m01) in toluene (6d) with vigorous stirring, add ethylamine (70% aqueous solution) at 5 to 10°C.
6d was added at once. After stirring at room temperature for 15 hours, the same post-treatment as in production side 1 was carried out to obtain the desired compound of the present invention (
2) 140 SIP was obtained as a yellow oil. n
22°91.5929 Production side 8 4-chloro-4-trifluoromethylsulfonyloxybenzophenone-N'-acetylhydrazone 800q (
0.71 mmol), phosphorus pentachloride 68M9CO, 78
A mixture of p-xylene (mmol) and p-xylene 5III/ was heated under reflux for 10 hours under a nitrogen atmosphere. After the reaction is complete,
The mixture was cooled to 5-10°C and with vigorous stirring was added 10 ml of N-methyl N-ethylamine (50% aqueous solution).
d was added all at once. After stirring at room temperature for 8 hours, the production side 1 and the other post-treatments were carried out to obtain the desired compound of the present invention (2).
265 was obtained as a yellow oil. n28・6 D 1.5980 Production side 4 4-chloro-4-trifluoromethylsulfonyloxybenzophenone = N'-acetylhydrazone 800! (
0.71 mmol), oxychloride: / 1201
A mixture of y (0.78 mmol) and 51 Il/toluene was heated under reflux for 10 hours under a nitrogen atmosphere. After the reaction was completed, the mixture was cooled to 5-10°C and 10 t of diethylamine (50% aqueous solution) was added to it with vigorous stirring.
t was added at once. After stirring at room temperature for 5 hours, the same post-treatment as in production side 1 was carried out to obtain the desired compound of the present invention (11
) 145 W was obtained as a yellow oil. n24°0
1.5920 The compounds of the present invention produced according to the above production method are shown in Table 1 below, but of course the present invention is not limited thereto.

General formula % formula %)) Formulation example 1 Compounds (1) to (4), (6), (7) +
Each oil agent is obtained by mixing 0.2 parts of each of (9) to (12) and (14), 2 parts of xylene, 2 parts of DM1i', and 95.8 parts of white kerosene.

Formulation Example 2 10 parts each of compounds (1) to (80), 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 85 parts of xylene, and D
15 parts of MF are thoroughly mixed to obtain each emulsion.

Formulation Example 8 Two parts each of compounds (1) to (80), 10 parts of fenitrothion, 8 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 65 parts of synthetic hydrated silicon oxide were thoroughly ground and mixed to form a hydrated product. get the agent.

Formulation Example 4 1 part of each of Compounds (1) to (80), 2 parts of Carbaryl, 87 parts of kaolin clay, and 10 parts of talc are thoroughly ground and mixed to obtain each powder.

Formulation Example 5 Compounds (su, (2), (4), (10),
(fl), (17).

To 5 parts each of (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 were added and mixed with vigorous stirring. Then, an appropriate amount of water is added to these mixtures, which are further stirred, granulated using a granulator, and dried through ventilation to obtain each 596 granule.

Formulation Example 6 Compounds (1) to (4) l (6) + (7) +
0.05 parts each of (9) to (12) and (14), 0.2 parts of tetramethrin, 0.06 parts of methrin (29), 7 parts of xylene, and 42 parts of deodorized kerosene.
．． After mixing and dissolving 7 parts, filling an aerosol container and attaching a valve part, 50 parts of a propellant (liquefied petroleum gas) was pressurized and filled through the valve part to obtain each aerosol.

Formulation Example 7 Compounds (1), (2), (4), (10)
, (11), (17), (18).

(20) and 1.20 parts each of sorbitan trioleate.
5 parts and 28 parts of an aqueous solution containing 2 parts of polyvinyl alcohol.
．． 5 parts and finely grind it with a sand grinder (particle size 8
μ or less), to this was added 40 parts of an aqueous solution containing 0.06 parts of xanthan gum and 0.1 part of aluminum magnesium silicate, and further 1 part of propylene glycol.
Add 0 parts and mix with stirring to obtain each 20% suspension in water.

Formulation Example 8 Compounds (1) to (7) t (9) to i'! 2) ,
1 part each of (17), (18), and (22) was mixed with 8 parts of sesame oil, and to this was added 0.08 part of bu(80) hydroxyanisole, and 0 part of dehydroacetic acid.
．． Add 1 part of brown sugar, 10 parts of crystalline cellulose, and 55.87 parts of potato starch, mix uniformly, apply a pressure of 15 IF/32, and prepare 1 tablet (about 4 FC diameter: about 801 M). The compounds used for comparison are indicated by the compound numbers in the table, and the compounds used for comparison are indicated by the compound symbols in Table 2.

Test Example 1 (Insecticidal test against Spodoptera trifoliata) An emulsion of the test compound obtained according to Formulation Example 2 was mixed with water for 20 minutes.
2- of 0 times diluted solution (5001m) with a diameter of 11? 13I artificial feed for Spodoptera japonica was soaked into a polyethylene cup. There are 4 Spodoptera spp.
Ten instar larvae were released, and 6 days later, their survival and death were investigated to determine the dead fish rate (2 repetitions)1. The results are shown in Table 8.

Test Example 2 (Insecticidal test against Culex mosquito) The emulsion of the test compound obtained according to Formulation Example 2 was diluted 200 times with water, and 0.7 wt of the solution was added to 100- ion-exchanged water (effective Component concentration 8.51)ri5m). Twenty last-instar larvae of A. larvae were released into the larvae, and the percentage of dead fish after one day was determined.

The effectiveness criteria are Dead fish rate a: 90% or more b: 10% or more but less than 90% C: Less than 10% And so. The results are shown in Table 4.

Table 4 (88) (84) Test Example 8 (Insecticidal test against Southern Corn Root Fume) A water diluted solution (50 ppm) of the emulsion of the test compound obtained according to Formulation Example 2 was added to a tube with a diameter of 5.5 mm. Pour the drop onto a filter paper of the same size placed at the bottom of a prepared polyethylene cup, then add Southern Corn Root "7-A (0 eggs, 20-80 eggs, and 1 kernel of corn sprouts) and cover the cup. After 3 to 8 days, the larvae will be removed. We investigated whether the fish were alive or dead and determined the dead rate.

The effectiveness criteria are Dead fish rate a: 100% b: 9096 or more but less than 100% C: Less than 90% And so. The results are shown in Table 5.

Table 1 Test Example 4 (Insecticidal test against K. chinensis) Formulation Example 2
An emulsion of the test compound obtained according to 20.
20 m of the 1:000 diluted solution (5p1) was sprayed onto rice plants planted in plastic cups with a diameter of 73 cm and a depth of 7 a, which had been inoculated with about 20 larvae of the 8th to 4th instar of the brown borer the previous day.

The survival or death of the larvae was examined 8 days after the drug treatment (2 repetitions).

The results are shown in Table 6.

Test Example 5 (Pre-meal test for German cockroaches) An acetone solution of the test compound was added to solid feed for mice and rats (
Solid feed CF for Japan Talea breeding! -2) Dropped at 0.5F to obtain 1% drug-treated bait (poisoned bait). Bottom diameter 11
In a polyethylene container with a height of cII11 and a height of 101aII, chemically treated bait and untreated bait in small cups (diameter 91411), water, and a paper shelter were placed, respectively. Twenty adult German cockroaches (10 male and female) were released into this container, and the rate of young dead insects was investigated after 8 days. The results are shown in Table 7.

(87) (88 Tiger) Test Example 6 (Pre-meal test against black wood ants) Dissolve 3 mg of the test compound in 0.3 d of acetone, process this solution into a mixture of 2 g of skim milk powder and tg of granulated sugar, and mix uniformly. After mixing, the acetone was air-dried to obtain 0.1% poison bait. Polyethylene cup (diameter 9.5 am, height 4
．． 5 cm) inside the plastic mounting cup (2 cm diameter).
0.3 g of the poisoned bait and a cotton ball (diameter 1 cm) soaked in water were placed in a container (1 cm, height 1 cm). Ten adult black wood ants were released into this cup, and the survival rate was determined by examining whether they were alive or dead after 11 days. The results are shown in Table 8.

Table 8 <Effects of the Invention> The compounds of the present invention are effective against Lepidoptera pests, Diptera pests, Coleoptera pests,
It has excellent insecticidal efficacy against various insect pests such as Aphidroptera and Hymenoptera, and exhibits even greater insecticidal efficacy when ingested orally.

Claims (5)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 is substituted with a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, or an alkyl group with a total of 3 to 8 carbon atoms. an optional cycloalkyl group, 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 total carbon atoms, an optionally substituted phenyl group, or Represents an optionally substituted phenoxyalkyl group having 8 to 10 carbon atoms in total. R^2 is an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group optionally substituted with an alkyl group having 3 to 8 carbon atoms in total, and 3 to 8 carbon atoms.
alkenyl group, an alkynyl group having 3 to 8 carbon atoms, an optionally substituted aralkyl group having 7 to 10 total carbon atoms, an optionally substituted phenyl group, or a total carbon number of 8 to 1
Represents a phenoxyalkyl group which may be substituted with 0. However, R^1 and R^2 do not represent a methyl group at the same time. Furthermore, R^1 and R^2 may be bonded at their terminals to form a ring, and the ring may contain an oxygen atom, a sulfur atom, or a nitrogen atom. ] (2) Compounds represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and general formulas ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 is 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 in total, an alkenyl group having 3 to 8 carbon atoms, an alkynyl group having 3 to 8 carbon atoms, a substituted cycloalkyl group having 7 to 10 carbon atoms in total; represents an optionally substituted aralkyl group, an optionally substituted phenyl group, or an optionally substituted phenoxyalkyl group having 8 to 10 carbon atoms in total. R^2 is an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group optionally substituted with an alkyl group having 3 to 8 carbon atoms in total, and 3 to 8 carbon atoms.
alkenyl group, an alkynyl group having 3 to 8 carbon atoms, an optionally substituted aralkyl group having 7 to 10 total carbon atoms, an optionally substituted phenyl group, or a total carbon number of 8 to 1
Represents a phenoxyalkyl group which may be substituted with 0. However, R^1 and R^2 do not represent a methyl group at the same time. Furthermore, R^1 and R^2 may be bonded at their terminals to form a ring, and the ring may contain an oxygen atom, a sulfur atom, or a nitrogen atom. ] The method for producing a hydrazone compound according to claim 1, characterized in that the hydrazone compound is reacted with an amine compound represented by the following. (3) Compounds represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and general formulas ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 is 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 in total, an alkenyl group having 3 to 8 carbon atoms, an alkynyl group having 3 to 8 carbon atoms, a substituted cycloalkyl group having 7 to 10 carbon atoms in total; represents an optionally substituted aralkyl group, an optionally substituted phenyl group, or an optionally substituted phenoxyalkyl group having 8 to 10 carbon atoms in total. R^2 is an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group optionally substituted with an alkyl group having 3 to 8 carbon atoms in total, and 3 to 8 carbon atoms.
alkenyl group, an alkynyl group having 3 to 8 carbon atoms, an optionally substituted aralkyl group having 7 to 10 total carbon atoms, an optionally substituted phenyl group, or a total carbon number of 8 to 1
Represents a phenoxyalkyl group which may be substituted with 0. However, R^1 and R^2 do not represent a methyl group at the same time. Furthermore, R^1 and R^2 may be bonded at their terminals to form a ring, and the ring may contain an oxygen atom, a sulfur atom, or a nitrogen atom. ] The method for producing a hydrazone compound according to claim 1, characterized in that the hydrazone compound is reacted with an amine compound represented by the following. (4) An insecticide containing the hydrazone compound according to claim 1 as an active ingredient. (5) The insecticide according to claim 4, wherein the insecticide is a food poison type insecticide.