JP3068846B2 - Novel hydrazine derivative and insecticidal composition containing the same as active ingredient - Google Patents

Description

The present invention relates to a novel hydrazine derivative, which can be used as a pesticide in paddy fields, uplands, orchards, forests or environmental hygiene situations. . In addition, the derivative can be used as a parasite control agent for protecting humans or animals from parasite damage.

[Conventional technology]

JP-A-62-167747 discloses that N'-substituted-N, N'-diacylhydrazine derivatives have insecticidal activity, and JP-A-62-263150 discloses N-substituted-N'-substituted. It is described that -N, N'-diacylhydrazine derivatives have insecticidal activity. However, these patents do not specifically describe the derivatives of the present invention described below.

[Problems to be solved by the invention]

In pest control scenes in paddy fields, uplands, orchards, forests, or environmental hygiene scenes, there is a demand for compounds that have greater insecticidal activity and properties that do not harm the beneficial insects and the environment, and that have low toxicity. I have. In addition, recently, pests exhibiting resistance to known insecticides such as organophosphorus agents, carbamate agents, pyrethroid agents and the like have increased, making it difficult to control, and new types of agents have been required.

The present invention provides a new type of insecticidal compound that does not substantially harm beneficial insects, the environment, etc., has low toxicity and is also effective against drug-resistant pests, and an insecticidal composition containing the same as an active ingredient. It is intended to be.

[Means for solving the problem]

As a result of intensive research to achieve the above objective, the general formula [Wherein X ₁ and X ₂ are the same or different and are O, S or NR, and R ₁ represents a (C ₁ -C ₄ ) alkyl group, and R ₂ , R ₃ , R ₄ and
R ₅ is independently a hydrogen atom, a halogen atom, (C ₁ to
C ₄₎ alkyl group, (C ₂ ~C ₅₎ alkenyl, (C ₂ ~C ₅₎
Alkynyl group, (C ₁ ~C ₄₎ haloalkoxy group, (C ₁ ~
C ₄ ) represents an alkoxy group, a cyano group or a nitro group. And R ₆ is a hydrogen atom, a cyano group, SR ₁₀ (where R ₁₀ represents a halomethyl group) or a halogen atom, OR ₁₁ (where R ₁₁ is a hydrogen atom, a (C ₁ -C ₄ ) alkyl group, _{1 ~C 4)}
(C ₁ -C ₄ ) alkyl group, (C ₂ -C ₄ ) alkynyl group or (C ₂ -C ₄ ) alkenyl group which may be substituted. R ₇ is an unsubstituted (C ₄
〜C ₁₀ ) alkyl or a (C ₁ -C ₄ ) linear alkyl group substituted by one or two same or different (C ₃ -C ₆ ) cycloalkyl, wherein R ⁸ and R ⁹ are the same. A hydrogen atom, a (C ₁ -C ₄ ) lower alkyl group or a fluorine atom which may be different. The present inventors have found that the novel hydrazine derivative represented by the formula (1) has excellent insecticidal activity and completed the present invention.

The compound of the general formula (I) of the present invention can be produced by the following method. That is, it is represented by the general formula (II).

With hydrazide [Wherein, X ₁ , R ₁ , R ₂ , R ₇ , R ₈ , and R ₉ have the same meaning as described above. A benzoyl halide represented by the general formula (III) Wherein X ₂ , R ₃ , R ₄ and R ₅ have the same meaning as described above,
X represents a halogen atom. To give a compound of the general formula (I) (R ₆ is a hydrogen atom).

In the reaction, the compound of the general formula (II) and the compound of the general formula (III) can be used in any ratio, but preferably in an equimolar ratio or an approximately equimolar ratio. As the solvent, a solvent inert to the reactants can be used. For example, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons such as benzene, toluene and xylene,
Examples include halogenated hydrocarbons such as chloroform, dichloromethane, and chlorobenzene, ethers such as diethyl ether and tetrahydrofuran, and nitriles such as acetonitrile and propionitrile. A mixed solvent of these and a mixed solvent of these and water can also be used. As the base, for example, an inorganic base such as potassium hydroxide or sodium hydroxide, or an organic base such as triethylamine or pyridine can be used. When an organic base such as triethylamine or pyridine is used, it can be used as a solvent in a large excess. The amount of the base can be used in a stoichiometric amount or in excess, but preferably an amount in which the stoichiometric amount is in excess of 1.0 to 5.0 times is used. The reaction can be carried out in a temperature range from -20 ° C to the boiling point of the solvent, and preferably in the range of 0 ° C to 50 ° C. N, N ′
-A catalyst such as dimethylaminopyridine may be added to the reaction system.

In the compound of the general formula (I), R ₆ is a cyano group, SR
₁₀ (however, R ₁₀ represents a halomethyl group) or a halogen atom, OR ₁₁ (where R ₁₁ represents a hydrogen atom, a (C ₁ -C ₄ ) alkyl group, or a (C ₁ -C ₄ ) acyl group) Compounds of an alkyl group, an alkynyl group, and an alkenyl group which may be reacted with a compound in which R ₆ is a hydrogen atom in the presence of a base such as sodium hydride in an inert solvent such as tetrahydrofuran, N,
It can be obtained by reacting with a corresponding halide such as cyanogen bromide propyl bromide propargyl bromide, aryl bromide halogenosulfenyl halide in N'-dimethylformamide or the like.

The compound of the general formula (II) used for producing the compound of the general formula (I) is represented by the general formula (IV) corresponding to the compound of the formula (V). It can be obtained by reacting with benzoyl halide. The reaction is illustrated below.

[Wherein X ₁ , R ₁ , R ₂ , R ₇ , R ₈ , R ₉ and X have the same meanings as described above. The conditions for the reaction, such as the solvent and the reaction temperature, are the same as those used for the reaction between the compound of the general formula (II) and the compound of the general formula (III).

Compounds of the general formula (II) are represented by the formulas (VI) and (VII)
With the ketone or aldehyde of the intermediate product (VI
II) is obtained. Then, it can be obtained by reacting this with a reducing agent in an inert solvent.

[Wherein, X ₁ , R ₁ , R ₂ , R ₈ , and R ₉ represent the same meaning as described above, and R ₁₁ and R ₁₂ represent a hydrogen atom or a C ₁ -C ₁₀ alkyl group.] I) The compound can be obtained by reacting a benzoyl halide represented by the general formula (IV) with a hydrazide represented by the general formula (IX). The reaction is illustrated below.

Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and X have the same meaning as described above. The conditions for the reaction, such as the solvent and the reaction temperature, are the same as those used for the reaction between the compound of the general formula (II) and the compound of the general formula (III).

The reaction mixture at the time of producing the compound of the general formula (I) or the compound of the general formula (II) is stirred for a sufficient time, and the desired product is recovered by a usual post-treatment such as extraction, washing, drying and solvent distillation. You. Although simple solvent washing is often sufficient, purification can be performed by recrystallization or column chromatography if necessary.

When the compound of the general formula (I) of the present invention is used, a method generally used in the field of agrochemical production may be used as it is according to the purpose of use or by mixing an agrochemical auxiliary for promoting or stabilizing the effect. Powders, fine granules,
Granules, wettable powders, flowables, emulsions, microcapsules, oils, aerosols, heated fumigants (mosquito coils, electric mosquito coils, etc.), fogging agents such as foking, non-heated fumigants, and bait It can be used as a composition in a pharmaceutical form.

These various preparations can be used directly as they are, or can be used after being diluted with water to a desired concentration.

Examples of the pesticidal auxiliary herein include a carrier (diluent) and other auxiliary agents such as a spreading agent, an emulsifier, a wetting agent, a dispersant, a fixing agent, and a disintegrant. As the liquid carrier, aromatic hydrocarbons such as toluene and xylene,
Alcohols such as butanol, octanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethylsulfoxide, methylnaphthalene, cyclohexanone, animal and vegetable oils,
Fatty acids, fatty acid esters and the like, as well as water of petroleum fractions such as kerosene and light oil, and the like can be mentioned.

Examples of the solid carrier include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, monomorillonite, bentonite, feldspar, quartz, alumina, sawdust and the like.

Surfactants are usually used as emulsifiers or dispersants, for example, anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine, and cationic surfactants. Agent,
Nonionic surfactants and zwitterionic surfactants are exemplified.

Examples of the spreading agent include polyoxyethylene nonylphenyl ether and polyoxyethylene lauryl ether. Examples of the wetting agent include polyoxyethylene nonylphenyl ether dialkyl sulfosuccinate. Methyl cellulose,
Examples thereof include polyvinyl alcohol, and examples of the disintegrant include sodium ligninsulfonate and sodium lauryl sulfate.

Further, these compounds of the present invention can exhibit more excellent insecticidal activity when used in combination of two or more kinds thereof, and can also exhibit other physiologically active substances such as arethrin, phthalthrin, permethrin, decamesulin, fenvalerate, and cyclopro- Pyrethroids and various isomers such as Trin, Pyrethrum extract, DDVP, Fenitrothion, Diazinon, Temefos and other organophosphate insecticides, NAC, MTM
Carbamate insecticides such as C, BPMC, and pyrimer, other insecticides, acaricides or fungicides, nematicides, herbicides, plant growth regulators, fertilizers, BT agents, insect hormones, and other pesticides. By mixing, a multipurpose composition having more excellent effects can be produced, and a surplus effect can be expected.

In addition, the efficacy can be multiplied by adding those known as synergists for pyrethroids, such as, for example, piperonyl butoxide, sulfoxide, safloxane.

The compound of the present invention has high stability to light, heat, oxidation and the like, but if necessary, an antioxidant or an ultraviolet absorber, for example, phenols such as BHT and BHA, arylamines such as α-naphthylamine or By adding a benzophenone-based compound as a stabilizer as appropriate, a more effective composition can be obtained.

The active ingredient content in the composition of the present invention is in the form of a formulation,
It depends on the method of application and other conditions. In some cases, only the active ingredient compound may be used, but usually 0.2 to 95% (weight)
Preferably, it is in the range of 0.5 to 80% (weight).

The amount of the composition of the present invention varies depending on the dosage form, the method of application, the timing, and other conditions.Agricultural and horticultural agents, agents for forest pests and agents for pastoral insect pests usually have an active ingredient amount of 10 per are. 300300 g, preferably 15-200 g, and the amount of the active ingredient for the sanitary insect-controlling insect is usually ² to 200 mg, preferably 5 to 100 mg, per m ² . For example, powder is 15-120 g of active ingredient per 10 ares, and granule is 30-240 g of active ingredient.
g, the emulsion and the wettable powder are the active ingredients in the range of 40 to 250 g. However, in special cases, it is possible, and sometimes even necessary, to exceed or fall below these ranges.

In order to control parasites, the compound represented by the general formula (I)
When using a compound of 0.1 to 200 mg / kg per body weight
Can be used. The exact dosage for a given condition can be determined routinely and depends on a variety of factors, including the substance used, the type of parasite, the formulation used and the condition of the human or animal affected by the parasite. Dependent.

Specific pest names to which the insecticidal composition of the present invention can be applied are listed.

From the order of the Hemiptera, for example, the leafhopper (Nephotettix cincticeps), the brown planthopper (Sogatell)
a furcifera), brown planthopper (Nilaparvata lugen)
s), Groundhopper, Laodelphax striatellus, Riptortus clavatus, Southern stink bug (Nezara viridula), Nashigumbai (Stephanit)
is nashi), Whiteflies (Trialeurodes vapor)
ariorum), cotton aphids (Aphis gossypii), peach moth aphids (Myzus persicae), wild scabies (Unasqis yanonensis), lepidoptera (Lepidopters), for example, Phyllonorycter ringoneell
a), Konaga (Plutella xylostella), Cotton moth (Prom
alactis inonisema) and Scarlet Monamaki (Adoxophyes)
orana), legume squirt (Leguminivora glycinivorel)
la), Coleoptera (Cnaphalocrocis medinalis), Coleoptera (Chilo supperessalis), Awanomeiga (Ost)
rinia furnacalis, armyworm (Mamestra brassica)
e), armyworm (Pseudletia separata), lotus armyworm (Spodoptera litura), rice beetle (Parnara g)
uttata), cabbage butterfly (Pieris rapae crucivor)
a), Heliothis (Heliothis spp.), Noctuid (Agrotis s)
pp.), from the order Coleoptera, e.g., Douganebuui (Anomala cuprea), Mamekogane (Popillia jap.)
onica), rice weevil (Echinocnemus soqameus), rice weevil (Lissorhoptrus oryzophilus), rice dwarf beetle (Oulema oryzae), beetle beetle (Anthrenus verbasic), cochnusto (Tenebroide)
s mauritaicus, weevil (Sitophilus zeamai)
s), the scorpion ladybird (Henosepilachna vigint)
ioctopunctata), Adzuki beetle (Callosobruchus ch)
inensis), Monochamus alternatus (Monochamus altern)
atus), cricket beetle (Aulacophora femoralis), Leptinotarsa decemlineata (Leptinotarsa decemline)
ata), Phedon cochleari
ae), Diabrotica (Diabrotica spp.), Hymenoptera [Hym
enoptera], for example, a wasp (Athalis ro
sae japonensis), Lulich Range bee (Arge sim)
ilis), as Diptera, for example, Culex pipiens fatigans, Aedes aegypti (Ae
des aegypti), soybean flies (Asphondylis s)
p.), fly (Hylemya platura), housefly (Musca)
domestica vicina) and sea fly (Dacus cucurbita)
e), rice leaf flies (Agromyza oryzae), flies (Lucilia spp.), human mines (Pulex irritans) as the order Aphaniptera, Xenops flea (Xenops)
ylla cheopis, dog flea (Ctenocephalides cani)
s), Thrips palmi (Scirtothrips dorsalis), Negi (Thysanoptera) as Thysanoptera
hrips tabaci), Thrips palmi (Thrips pal)
mi), rice thrips (Baliothrips biformis) and lice (Anoplura), for example, white lice (Pedi
culus humanus corporis, psyllium (Pthirus pubi)
s), as the order Psocoptera, for example, Tropium pulsatorium, Lipocelis bostrychophilus, orthoptera [Orthopter]
a) as mushrooms (Gryllotalpaafricana), locust migratoria (Locusta migratoria),
nsis), German cockroach (Blattella germanica),
Black cockroach (Periplaneta fuliginosa).

The most important parasites afflicting humans to which the insecticidal composition of the present invention can be applied and the diseases caused thereby are summarized below, but not limited thereto.

[Examples] Hereinafter, the present invention will be described with reference to Examples, but the present invention is not limited thereto.

Production Example 1. 2-Methyl-3,4-methylenedioxybenzoyl chloride (synthesis example of the compound represented by the general formula (IV)): 17.4 g of chromium (VI) oxide is dissolved in 19 ml of concentrated sulfuric acid and 87 ml of water. To a solution of 5.73 g of -methyl-3,4-methylenedioxybenzaldehyde in 200 ml of acetone is added dropwise at 0 ° C with vigorous stirring. After completion of the dropwise addition, the mixture was stirred at 0 ° C. for 1 hour, returned to room temperature, and further stirred for 6 hours. The temperature was returned to 0 ° C again, and 25 ml of isopropanol was added dropwise. After returning to room temperature, the mixture was stirred for 30 minutes, and decanted four times using an appropriate amount of acetone. The solvent was distilled off under reduced pressure, and water and ethyl acetate were added for extraction. The organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. A 10% aqueous sodium hydroxide solution and diethyl ether were added for extraction, and the aqueous layer was acidified with hydrochloric acid. The precipitated crystals were dissolved in ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to give 2-methyl-3,
4.76 g of 4-methylenedioxybenzoic acid were obtained. (Yield 76
%) Then 2-methyl-3,4-methylenedioxybenzoic acid
2.97 g of thionyl chloride (3.6 ml) was added to chloroform (40 ml), and the mixture was heated under reflux for 6 hours. Excess thionyl chloride and the solvent were distilled off to obtain 3.06 g (yield: 93%) of the desired 2-methyl-3,4-methylenedioxybenzoyl chloride.

Production Example 2. N- (2-methyl-3,4-methylenedioxy) benzoyl-N'-tert-butylhydrazide (Synthesis example of compound represented by general formula (II)): tert-butylhydrazine hydrochloride 3.08 g and a 10% aqueous sodium hydroxide solution (19.8 g) were added to methylene chloride (20 ml), and 2-methyl-3,4-methylenedioxybenzoyl chloride (3.06 g) was added dropwise in an ice water bath. After stirring overnight, water and ethyl acetate were added for extraction. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and N- (2-methyl-3,4-methylenedioxy) benzoyl-N'-tert-butylhydrazide was obtained in an amount of 3.25 g.
(84% yield).

Production Example 3. N- (2-methyl-3,4-methylenedioxy) benzoyl-N'-tert-butyl N'-benzoylhydrazine (Compound No. 1); N- (2-methyl-3,4-) 0.666 g of methylenedioxy) benzoyl-N'-tert-butylhydrazide in pyridine
It was dissolved in 13 ml and a catalytic amount of dimethylaminopyridine was added. Under an ice-water bath, benzoyl chloride (0.39 g) was added dropwise, and the mixture was returned to room temperature and stirred with ugliness. Ethyl acetate and 5% hydrochloric acid were added for extraction. The organic layer was further washed with 5% hydrochloric acid, dried over anhydrous magnesium sulfate washed with water, filtered, and the solvent was distilled off under reduced pressure. The obtained crystals were washed with a mixed solvent of n-hexane and diethyl ether and dried. Target N
-(2-methyl-3,4-methylenedioxy) benzoyl-N'-tert-butyl-N'-benzoylhydrazine
81 g (88% yield, mp 219-222 ° C.) were obtained.

Production Example 4. N- (2-methyl-3,4-methylenedioxy) benzoyl-N'-tert-butyl-N '-(3'-methyl) benzoylhydrazine (Compound No. 3); N- (2 0.45 g of -methyl-3,4-methylenedioxy) benzoyl-N'-tert-butyl-hydrazide was dissolved in 10 ml of pyridine and extracted with a catalytic amount of dimethylaminopyridine. Further, the organic layer was washed with 5% hydrochloric acid and washed with water.

After drying over anhydrous magnesium sulfate and filtration, the solvent was distilled off under reduced pressure. The obtained crystals were washed with a mixed solvent of n-hexane and diethyl ether and dried. Target N-
(2-methyl-3,4-methylenedioxy) benzoyl-
5.68 g (85% yield) of N'-tert-butyl-N '-(3', 5'-dimethyl) henzoylhydrazine were obtained. Melting point 189
-191 ° C.

Next, Table 1 shows typical examples of the compound represented by the general formula (I) according to the present invention.

Next, the insecticidal composition will be specifically described using formulation examples.

Formulation Example 1. Emulsion To 20 parts of Compound No. 1 were added and dissolved 65 parts of a mixture of xylene-methylphthalene, and then a mixture of alkylphenol ethylene oxide condensate and calcium alkylbenzene sulfonate (8: 2) 15 Parts were mixed to form an emulsion. The present invention is diluted with water and used as a spray liquid.

Formulation Example 2. Wettable powder 20 parts of compound No. 1 and 35 parts of carion and 30 clay
And sodium laurate and sodium dinaphthylmethanesulfonate (1: 1).
1) 7.5 parts were mixed and pulverized to obtain a powder. The drug is diluted with water and used as a spray liquid.

Formulation Example 3 Dust A 97 parts mixture of talc and calcium carbonate (1: 1) is added to 1 part of the compound of Compound No. 8, and the mixture is ground and thoroughly dispersed and blended. Then, 2 parts of silicic anhydride is further added. It was mixed and pulverized to obtain a powder. Spray this agent as it is.

Formulation Example 4. Granules Compound No. 8 (2 parts) was mixed with bentonite fine powder 48
Parts, 48 parts of talc and 2 parts of sodium ligninsulfonate, and then water is added and kneaded until uniform. Next, the mixture was granulated through an injection molding machine, passed through a granulator and a dryer sieve to obtain granules having a particle size of 0.6 to 1 mm. The drug is used by directly dispersing it on paddy and soil surfaces.

Formulation Example 5. Oil solution To 0.1 part of the compound of Compound No. 1 was added 0.5 part of piperonibutoxide and dissolved in white kerosene to make the whole 100 parts to obtain an oil solution. Use this drug as is.

Next, the biological effect of the compound represented by the general formula (I) according to the present invention will be specifically described by test examples.

Test Example 1. Effect on Japanese moth (Foliage dipping method) A 20% wettable powder or a 20% emulsion of the compound of the present invention was produced according to Formulation Examples 1 and 2, and was used as a test drug. MEP 50% emulsion and cypermethrin 6% emulsion were used as control drugs.

Test method: The middle leaves of cabbage grown to about 10 cabbage true leaves were cut off and immersed for 20 seconds in a treatment solution diluted with water so that the active ingredient of each reagent was 200 ppm. After air-drying, place in a 9 cm diameter plastic container,
0 animals were released. The container was covered with a lid having 5 to 6 small holes, and allowed to stand in a low-temperature room at 25 ° C. Four days after the treatment and release, the number of live and dead insects was examined, and the mortality was calculated. The results are shown in Table 2 as an average of duplicates. In addition, this Konaga was used from Ageo, a susceptible strain, and from Kagoshima, which is resistant to organophosphates, carbamates, pyrethroids and the like.

Test Example 2 Effect on Spodoptera litura A 20% wettable powder or a 20% emulsion of the compound of the present invention was produced according to Formulation Examples 1 and 2, and used as a reagent.

Test method: The middle leaves of cabbage grown to about 10 cabbage true leaves were cut off and immersed for 20 seconds in a treatment solution diluted with water so that the active ingredient of each reagent was 200 ppm. After air-drying, two treated leaves were placed in a plastic container having a diameter of 9 cm, and five third-instar larvae of Spodoptera litura were released into the container. The container was covered with a lid having five or six small holes, and allowed to stand in a low-temperature room at 25 ° C. Four days after the treatment and release, the number of live and dead insects was examined, and the mortality was calculated. The results are shown in Table 3 as the average of triplicates.

Test Example 3 Effect on Kobumemeiga 20% wettable powder or 20% emulsion of the compound of the present invention was produced according to Formulation Examples 1 and 2, and used as a reagent.

Test method: 10 rice plants in the 3 leaf stage were treated with the active ingredient of each reagent.
It was immersed in a treatment solution diluted with water to 200 ppm for 20 seconds. After air drying, the rice is rolled with urethane and the glass inner cylinder (44
mm, 140mm in height)
After the head was released, the upper part of the glass cylinder was covered with a paper envelope. The glass cylinder was allowed to stand at 25 ° C. in a constant temperature room for 16 hours in the light period. Five days after the treatment and release, the number of live and dead insects was investigated.
The mortality was calculated. In addition, the test was performed in a two-consecutive manner. The results are shown in Table 4.

Test Example 4. Effect on Anopheles serrata A 20% wettable powder or a 20% emulsion of the compound of the present invention was produced according to Formulation Examples 1 and 2, and used as a reagent.

Test method: Seven tea leaves having a length of about 5 cm were immersed for 20 seconds in a treatment solution diluted with water so that the active ingredient of the reagent was 200 ppm. After air-drying, they were placed in a plastic container (inner diameter 70 mm, height 40 mm), and five third instars of the Anemone brassicae were released. Cover the container with 5 or 6 small holes,
It was left still in a constant temperature room at 25 ° C for 16 hours in the light period. Five days after the treatment and release, the number of live and dead insects was examined, and the mortality was calculated.
In addition, the test was performed in a two-consecutive manner. The results are shown in Table 5.

[Effects of the Invention] The present invention is configured as described above with reference to the embodiments, and has the following effects.

The hydrazine derivative of the present invention has an excellent insecticidal effect against pests that are resistant to known insecticides such as organophosphates, pyrethroids, etc., and can be used in paddy fields, uplands, orchards, forests, or environmental sanitation. It is effective in controlling scenes.

──────────────────────────────────────────────────続 き Continuation of front page (56) References JP-A-62-167747 (JP, A) JP-A-62-175451 (JP, A) JP-A-3-5446 (JP, A) JP-A-3-3 141245 (JP, A) JP-A-4-89471 (JP, A) US Pat. No. 4,814,349 (US, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C07D 317/00-317/72 A01N 43/28-43/30 CA (STN) REGISTRY (STN)

Claims (4)

(57) [Claims] (1) General formula [Wherein X ₁ and X ₂ are the same or different and are O, S or NR, R ₁ represents a (C ₁ -C ₄ ) alkyl group, and R ₂ , R ₃ , R ₄ and R ₅
Are independently a hydrogen atom, a halogen atom, (C ₁ -C ₄ )
Alkyl group, (C ₂ -C ₅ ) alkenyl group, (C ₂ -C ₅ ) alkynyl group, (C ₁ -C ₄ ) haloalkoxy group, (C ₁ -C ₄ ) haloalkyl group, (C ₁ -C ₄₎ ) Represents an alkoxy group, a cyano group or a nitro group. And R ₆ is a hydrogen atom, a cyano group, SR
₁₀ (however, R ₁₀ represents a halomethyl group) or a halogen atom, OR ₁₁ (where R ₁₁ represents a hydrogen atom, a (C ₁ -C ₄ ) alkyl group, or a (C ₁ -C ₄ ) acyl group) And (C ₁ -C ₄ ) alkyl, (C ₂ -C ₄ ) alkynyl and (C ₂ -C ₄ ) alkenyl. R ₇ is substituted with an unsubstituted (C ₄ -C ₁₀ ) alkyl group having a tertiary carbon atom or with one or two identical or different (C ₃ -C ₆ ) cycloalkyl (C ₁ -C ₄ ) Represents a linear alkyl group, R ₈
And R ₉ represent a hydrogen atom, a lower alkyl group or a fluorine atom which may be the same or different. ] The hydrazine derivative represented by these. 2. X ₁ and X ₂ may be the same or different O or S
R ₁ represents a (C ₁ -C ₂ ) alkyl group substituted at the 2-position, R ₂ represents a hydrogen atom, and R ₃ , R ₄ and R ₅ each independently represent a hydrogen atom, a halogen atom, ( C ₁ -C ₄ ) represents an alkyl group or a nitro group, R ₆ represents a hydrogen atom, a cyano group or SR ₁₀ (where R ₁₀ represents a halomethyl group), and R ₇ represents a tertiary carbon atom. Represents a substituted (C ₄ -C ₁₀ ) alkyl group;
The hydrazine derivative according to claim 1, wherein ₈ and R ₉ represent a hydrogen atom. (3) wherein X ₁ and X ₂ represent O or S which may be the same or different, R ₁ represents a methyl group substituted at the 2-position, R ₂ represents a hydrogen atom, R ₃ , R _{3 4} and R ₅ each independently represent a hydrogen atom, a halogen atom, a (C ₁ -C ₄ ) alkyl group or a nitro group, and R ₆ represents a hydrogen atom, a cyano group or SR ₁₀ (where R ₁₀
Represents a halomethyl group. R ₇ represents an unsubstituted (C ₄ -C ₁₀ ) alkyl group having a tertiary carbon atom, and R ₈ and R
The hydrazine derivative according to claim 1, wherein ₉ represents a hydrogen atom. 4. An insecticidal composition comprising a hydrazine derivative represented by the general formula (I) according to any one of claims (1) to (3) as an active ingredient. Stuff.