JPH0539252A - N, n'-dibenzoyl-butylhydrazine derivative and insecticidal composition comprising the same derivative as active ingredient - Google Patents

Abstract

PURPOSE:To obtain an N,N'-dibenzoyl-t-butylhydrazine derivative, showing excellent effects on a chemical-resistant insect pests, not damaging environment, having low toxicity to humans and animals and insecticidal activity of new type. CONSTITUTION:A compound shown by formula I {R<1> to R<4> are H, halogen, nitro, cyano, 1-4C (halo) alkyl, 2-4C alkenyl, 2-4C alkynyl, 1-4C (halo) alkoxy [when two adjoining positions are replaced with (halo) alkoxy, groups may be bonded to form 5- to 6-membered dioxolano or dioxano]; R<5> is 1-4C alkyl or 2-4C alkenyl; R<6> is H, 1-4C alkyl, 2-4C alkenyl or 2-4C alkynyl} such as N'-t-butyl-N'-(6-fluoro-3-methylbenzoyl)-N-2,3dimethylbenzoylhydrazine. The compound shown by formula I, for example, is obtained by reacting a compound shown by formula II with a compound shown by formula III (X is halogen) in a solvent in the presence of a base.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel N, N'-dibenzoyl-tert-butylhydrazine derivative which is used as an insecticide in paddy fields, uplands, orchards, forests or environmental hygiene scenes. be able to.
Further, the derivative can be used as a parasite control agent for protecting humans or animals from parasite damage.

[0002]

2. Description of the Prior Art Japanese Patent Laid-Open No. 62-167747 discloses N'-
Substituted-N, N'-diacylhydrazine compounds are also disclosed in JP-A-62-263150, N-substituted-N'-substituted-.
It is described that N, N'-diacylhydrazine compounds are useful as insecticides. However, the above patent does not specifically describe the derivative of the present invention.

[0003]

In recent years, resistance of insect pests to conventional insecticides such as organic phosphorus agents, carbamate agents and pyrethroid agents has been developed, resulting in paddy fields, uplands, orchards, forests or environmental hygiene. It has become difficult to control them in the scene. In addition, the environmental impact of these insecticides and the toxicity to humans and livestock have become major social problems, and new types of agents are required.

The present invention shows a new type of compound having an insecticidal activity which is effective against drug-resistant pests, does not harm the environment, and has low toxicity to humans and livestock, and an active ingredient thereof. It aims at providing the insecticidal composition.

[0005]

[Means for Solving the Problems] As a result of earnest research to solve the above problems, the general formula

[0006]

[Chemical 2]

[Wherein R ¹ , R ² , R ³ and R ⁴ are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a (C ₁ -C ₄ ) alkyl group, or (C ₁ -C ₄ ). haloalkyl, (C ₂ ~C ₄₎ alkenyl, (C ₂ ~
C ₄₎ alkynyl, (C ₁ ~C ₄₎ alkoxy group,
(C ₁ -C ₄ ) haloalkoxy group (when two adjacent positions are substituted with an alkoxy group or a haloalkoxy group, these substituents are bonded to form a 5- or 6-membered dioxolano or dioxano ring. May be formed).
R ⁵ represents a (C ₁ -C ₄ ) alkyl group, a (C ₂ -C ₄ ) alkenyl group, R ⁶ represents a hydrogen atom, a (C ₁ -C ₄ ) alkyl group, a (C ₂ -C ₄ ) alkenyl group , (C _{2 to} C ₄ )
The present invention has been completed by finding that the N, N'-dibenzoyl-tert-butylhydrazine derivative represented by [showing an alkynyl group] has an extremely high insecticidal effect.

The compound of the general formula (1) of the present invention can be produced by the following method. That is, the general formula (2)

[0009]

[Chemical 3]

[Wherein R ¹ , R ² and R ³ have the same meaning as described above. ] N-benzoyl-N'-te represented by
rt-Butylhydrazine and general formula (3)

[0011]

[Chemical 4]

[In the formula, R ⁴ and R ⁵ have the same meanings as described above, and X represents a halogen atom. ] It is obtained by reacting with a benzoyl halide represented by the following in the presence of a solvent and a base. The reactions are carried out in equimolar or nearly equimolar ratios, although it is possible to use either component in excess.

Examples of the solvent include aliphatic hydrocarbons such as hexane, heptane and petroleum benzine, halogenated hydrocarbons such as chloroform, dichloromethane and chlorobenzene, ethers such as diethyl ether and tetrahydrofuran.
Examples thereof include ters, nitriles such as acetonitrile and propionitrile, esters such as ethyl acetate, aproton-donating polar solvents such as dimethylformamide and dimethylsulfoxide, water, or a mixed solvent thereof.

Examples of the base include inorganic bases such as sodium hydroxide and potassium carbonate, and organic bases such as triethylamine and pyridine. The organic bases may be used in excess and used as a solvent. The base can be used in stoichiometric amount or in excess. The reaction temperature is -20 ° C to 100 ° C, preferably 0 ° C to 50 ° C. Further, 4-N, N-dimethylaminopyridine or the like can be added to the reaction system as a catalyst.

In the compound of the general formula (1), when R ⁶ represents a (C ₁ -C ₄ ) alkyl group, a (C ₂ -C ₄ ) alkenyl group or a (C ₂ -C ₄ ) alkynyl group, It can be manufactured by a method. That is, the general formula (4)

[0016]

[Chemical 5]

A compound represented by the formula [wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ have the same meanings as described above] and the general formula (5)

R ⁶ -X (5)

An alkyl halide represented by the formula: wherein R ⁶ has the same meaning as above and X represents a halogen atom,
It can be obtained by reacting an alkenyl halide and an alkynyl halide in the presence of a solvent and a base. The reactions are carried out in equimolar or nearly equimolar ratios, but the halide can also be used in excess.

Examples of the solvent include inert solvents such as dimethylformamide and tetrahydrofuran, which can be obtained by reacting a hydride such as propylpromide, allylpromide and propargylpromide in the presence of a base such as sodium hydride. it can. General formula (1)
The compound of the general formula (2) used for producing the compound of the above can be obtained by reacting t-butylhydrazine hydrochloride with the corresponding benzoyl halide represented by the general formula (6). The reaction is illustrated below.

[0021]

[Chemical 6]

[In the formula, R ¹ , R ² , R ³ and X have the same meanings as described above. Conditions for various reactions such as a solvent and a reaction temperature are the same as those used for the reaction between the compound of the general formula (2) and the compound of the general formula (3).

The reaction mixture during the production of the compound of the general formula (1) or the compound of the general formula (2) is stirred for a sufficient time and subjected to the usual post-treatments such as extraction, washing with water, drying, distilling off the solvent and the like. Is recovered. In many cases, a simple solvent washing is sufficient, but if necessary, purification can be performed by recrystallization or column chromography.

When the compound of the general formula (1) of the present invention is used, it is generally carried out in the field of pesticide production, either as it is or according to the purpose of use, or an agrochemical auxiliary is mixed in order to stabilize the effect. According to the method,
Fine granules, granules, wettable powders, flowables, emulsions, microcapsules, oils, aerosols, fumigants for heating (mosquito coils, electric mosquito coils, etc.), fuming agents for focking, etc. It can be used as a composition in any pharmaceutical form such as an agent or poison bait. In actual use, these various formulations can be used directly as they are or diluted with water to a desired concentration for use.

Examples of the agricultural chemicals auxiliary agent include carriers (diluents) and other auxiliary agents such as spreading agent, emulsifying agent, wetting agent, dispersing agent, fixing agent and disintegrating agent.
Examples of liquid carriers include aromatic hydrocarbons such as toluene and xylene, alcohols such as butanol, octanole, and glycol, ketones such as acetone, amides such as dimethylformamide, and dimethyl sulfoxide. Examples thereof include sulfoxides, methylnaphthalene, cyclohexanone, animal and vegetable oils, fatty acids, fatty acid esters, petroleum fractions such as kerosene and light oil, and water. Examples of solid carriers include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz,
Examples include alumina and sawdust.

A surfactant is usually used as the emulsifier or dispersant, and examples thereof include higher alcohol sodium sulfate, stearyl trimethyl ammonium chloride,
Examples thereof include anionic surfactants such as polyoxyethylene alkylphenyl ether and lauryl betaine, cationic surfactants, nonionic surfactants and zwitterionic surfactants. Examples of the spreading agent include polyoxyethylene nonylphenyl ether and polyoxyethylene lauryl ether, and examples of the wetting agent include polyoxyethylene nonylphenyl ether dialkyl sulfosuccinate. Examples of the fixing agent include carboxymethyl cellulose and polyvinyl alcohol, and examples of the disintegrating agent include sodium ligninsulfonate and sodium lauryl sulfate.

Furthermore, these compounds of the present invention can express more excellent insecticidal activity by using two or more kinds of them in combination, and other physiologically active substances such as allethrin, phthalthrin, permethrin, decamethrin, fuenvalere. -Pyrethroids such as cycloprotoline and various isomers, pyrethrum extract, DDVP, fenitrothion, diazinon, organophosphorus insecticides such as temephos, NAC, MTMC, BPMC, carina such as pirima
Bamate insecticides, other insecticides, acaricides or fungicides, nematicides, herbicides, plant growth regulators, fertilizers, B
By mixing with T agent, insect hormone agent and other agricultural chemicals, it is possible to prepare a multipurpose composition having more excellent efficacy, and it is also expected to have a synergistic effect. Furthermore, this effect can be increased several times by adding, for example, those known as synergists for pyrethroids such as piperonyl butoxide, sulphoxide and safroxan.

Further, the compound of the present invention is highly stable to light, heat, oxidation, etc., but if necessary, an antioxidant or an ultraviolet absorber, for example, phenols such as BHT and BHA, α-naphthylamine, etc. By appropriately adding the arylamines or benzophenone compounds described above as a stabilizer, a composition with more stable effects can be obtained. The content of the active ingredient in the composition of the present invention varies depending on the formulation form, method of application and other conditions, but in some cases, only the active ingredient compound is necessary, but usually 0.2 to 95%
(Weight) It is preferably in the range of 0.5 to 80% (weight).

The amount of the composition of the present invention to be used varies depending on the dosage form, the method of application, the time of application, and other conditions, but the agricultural and horticultural agent, the agent for forest pests and the agent for pests in the field are usually per 10 aal. The amount of active ingredient is 10 to 300 g, preferably 15 to 2
The amount of the active ingredient is ² to 200 mg, preferably 5 to 100 mg per 1 m2. For example, powder is 1 active ingredient per 10 aal.
5 to 120 g, granules are 30 to 240 g as an active ingredient, and emulsions and wettable powders are 40 to 250 g as an active ingredient. However, in special cases it is possible, and sometimes even necessary, to exceed or fall below these ranges.

When the compound of the general formula (1) of the present invention is used for controlling parasites, 0.1
It can be used in doses equivalent to ~ 200 mg / kg. The exact dosage for a given condition can be routinely determined and depends on various factors such as the quality used, the type of parasite, the formulation used and the condition of the human or animal affected by the parasite. Dependent.

Examples of specific pest names to which the insecticidal composition of the present invention can be applied are given below. From Hemiptere, for example, the leafhopper (Nephotettix cinctic-eps), the white-bellied planthopper (Sogatella furcifera), the brown planthopper (Nilaparva-talugens), and the brown planthopper (Laodelphax).
striatellus), the stink bug, R-iptortus clava
tus), Southern green stink bug (Nezaraviridula), Nashigumbai (Stephanitis nashi), White-flying whitefly (Tri
aleurodes vaperariorum), cotton aphid (Aphis go)
ssypii), green peach aphid (Myzus persicae), scale insect (Unasqis yanonensis), Lepidoptera (Lepi)
doptera] from, for example, Kimmon Hosoga (Phyllonoryct)
er ringoneella), diamondback moth (Plutella xylostella), cotton boll moth (Promalactis inonisema), and red beetle (A)
doxophyes orana), bean moth (Leguminivora glyc)
inivorella), Cobb Nomeiga (Cnaphalocr-ocis medinal)
is), Nikameiga (Chilo supperessalis), Awanomeiga (Ostrin-ia furnacalis), Spodoptera litura (Mamestra brassassic)
ae),

River armyworm (Pseudaletia separata), Lotus worm (Spodoptera litura), rice beetle (Par)
nara guttata), Pieris rapae cruciv
ora), Heliothis spp., Yaga (Agrotis spp.)
p.), from the order Coleoptera, for example, Dunebu buoy (Anomala cuprea), Japanese beetle (Popillia japonic)
a), rice weevil (Echinocnamus soqameus), rice weevil (Lissorhoptrus oryzophilus), rice dwarf beetle (Oulema oryzae), stag beetle (An-thre)
nus verbasci),

Coconut (Tenebroides mauritanicus)
, Sitophilus zeamais, Henosepilachna vigintioctopunctata, Red weevil, Callosobruchus chinensis, Pine beetle, Monochahamus alterna-tus, Beetle, Aul
acophora femoralis), Leptinotarsa decemlineata, Phaedon cochlear-iae, Diabrotica
ica spp.), as a Hymenoptera, for example, a turnip bee (Athalia rosaejaponensis), a Rurichu range bee (Argesi-milis), and as a diptera (Diptera), for example, Culex pipiens fatigans.
, Aedes aegypti, Soybean fly, Asphondylis sp., Fly fly, Hylemya platura
, Housefly (Musca domestica vicina),

Sea urchin fly (Dacus cucurbitae), rice leaf fly (Agromyza oryzae), fruit fly (Lucilia sp.
p.), as an Aphaniptera, a human flea (Pulex i
rritans), Keobusunezumimino (Xenopsylla cheopis)
, Flea (Ctenocephalidescanis), Thysanoptera
ptera] as a Thrips Thrips (Scirtothripsd
orsalis), Thrips tabaci, Thrips tabaci, Thrips palmi, Rice thrips (B
aliothrips biformis), as lice (Anoplura),
For example, white lice (Pediculus humanus corpois),
Lice (Pthirus pubis), Psocoptera (Psocopter)
a], for example, cochate (Trogium pulsatoriu
m), Hiratachate (Liposcelis bostrychophilus), and Orchid (Ortho-ptera) as kerula (Gryllotalpaaf rica)
na), locust locusts (Locusta migrat-oria), cobainago (Oxya yezoensis), German cockroach (Blattella)
germ-anica), Black cockroach (Periplaneta fuliginos)
a).

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

Disease product Bilharziosis or Schistosoma mansoni Schistosomiasis S. japonicum S. Haematobium (schistosome fluke, fluke worm or nematode) malayi (Nematode) Onchoceriasis or Onchocerca volvulus river blindness (Nematode) Loiasis Loa loa (Eye filamentous nematode)

[0037]

EXAMPLES The present invention will be described below with reference to examples.
The present invention is not limited to these. Production Example 1. N'-tert-butyl-N '(6-fluoro-
Preparation of 3-methylbenzoyl) -N-2,3-dimethylbenzoylhydrazine (Compound No. 1): N'-tert-butyl-N-2,3-dimethylbenzoylhydrazine (0.
54% of pyridine solution (5 ml) in catalytic amount of 4-N, N-
2-Fluoro-5-methylbenzoyl chloride (0.5 g) was added under ice-cooling in the presence of dimethylaminopyridine. After stirring overnight, the reaction mixture was poured into water and extracted with dichloromethane. The organic layer is 10% HCl
The extract was washed with water, water and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude crystals were recrystallized from n-hexane / acetic acid ethyl ester to give N'-tert-butyl-N '-(2-fluoro-5-
Methylbenzoyl) -N-2,3-dimethylhydrazine
0.54 g (yield 61.9%) was obtained.

Production Example 2. N'-tert-butyl-N '(4
Preparation of -Fluoro-3-methylbenzoyl) N-2,3-dimethylbenzoylhydrazine (Compound No. 6):
N'-tert-butyl-N-2,3-dimethylbenzoylhydrazine (0.8 g) in pyridine solution (10 ml) was added with a catalytic amount of 4
In the presence of -N, N-dimethylaminopyridine, 4-fluoro-3-methylbenzoyl chloride (0.
7g) was added. After stirring overnight, the reaction mixture was poured into water and extracted with dichloromethane. 10% organic layer
It was washed with HCl water, water and saturated saline, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained crude crystals were recrystallized from n-hexane / acetic acid ethyl ester to give N'-tert-butyl-N '-(4-fluoro-
1.19 g (yield 92.2%) of 3-methylbenzoyl) -N-2,3-dimethylhydrazine was obtained. Next, Table 1 shows typical examples of the compound represented by the general formula (1) according to the present invention.

[0039]

[Chemical 7]

[0040]

[0041]

[0042]

Next, the insecticidal composition will be specifically described with reference to formulation examples. Formulation Example 1. Emulsion 65 parts of a mixed solution of xylene-methylnaphthalene was added to 20 parts of the compound No. 1 and dissolved, and then 15 parts of a mixture of alkylphenol ethylene oxide condensate and calcium alkylbenzene sulfonate (8: 2) was mixed. To give an emulsion. This product is diluted with water and used as a spray solution.

Formulation Example 2. Wettable powder 20 parts of compound No. 1 with 35 parts of kaolin, clay
30 parts of diatomaceous earth and 7.5 parts of lauric acid
7.5 parts of a mixture of da and sodium dinaphthylmethanesulfonate (1: 1) were mixed and finely pulverized to obtain a powder. This product is diluted with water and used as a spray solution.

Formulation Example 3. Dust agent: 97 parts of a mixture of talc and calcium carbonate (1: 1) was added to 1 part of the compound of Compound No. 2, mixed and ground to sufficiently evenly disperse and mix, and then 2 parts of silicic anhydride was further added, mixed and pulverized, and powdered And Disperse this product as it is before use.

Formulation Example 4. Granules 2 parts of compound No. 2 bentonite fine powder 48
Part, talc 48 parts, and sodium lignin sulfonate 2 parts, and then add water and knead until uniform. Then, the mixture was granulated through an injection molding machine and passed through a granulator and a dryer to obtain granules having a particle size of 0.6 to 1 mm. This product is used by directly sprinkling it on the surface of paddy fields and the surface of soil.

Formulation Example 5. Oil agent Compound No. 1 (0.1 part) with piperonyl butoxide
0.5 part was added and dissolved in white kerosene to make 100 parts as a whole to obtain an oil solution. This product is used as it is.

Formulation Example 6. Azole Compound No. 6 compound 0.4 parts, Pipelor butoxide 2
After mixing and dissolving 0 part, 6 parts of xylene, and 7.6 parts of deodorized kerosene, and filling it in an aerosol container and attaching the valve part,
86 parts of Freon was pressure-filled through the valve portion to obtain an aerosol.

Formulation Example 7. Fumigated insecticidal composition of heated fiber: Dissolve 0.05 g of the compound of Compound No. 1 in an appropriate amount of chloroform and evenly adhere it to the surface of asbestos 2.5 cm x 1.5 cm 0.3 mm thick to obtain a fumigated insecticidal composition of heated fiber on a hot plate. It was

Formulation Example 8. Mosquito coil Incense Compound No. 1 (0.5 g) was dissolved in 20 ml of methanol, and 99.5 g of incense carrier (tab powder: meal powder: wood powder mixed at a ratio of 3: 5: 1) was stirred uniformly. After mixing and evaporating the methanol, 150 ml of water was added, and the mixture was thoroughly kneaded and molded and dried to obtain a mosquito coil. Next, the biological effects of the compound represented by the general formula (1) according to the present invention will be specifically described with reference to test examples.

Test Example 1. Effect on diamondback moth (Stem and leaf dipping method) A 20% wettable powder or 20% emulsion of the compound of the present invention was produced according to Formulation Examples 1 and 2 to give a reagent. MEP 50% emulsion and cypa-methrin 6% emulsion were used as control agents. Test method: The middle leaf of cabbage grown to about 10 cabbage true leaves is cut off, and the active ingredient of each reagent is 200 p
It was immersed for 20 seconds in a treatment liquid diluted with water so as to have pm. After air-drying, it was placed in a plastic container having a diameter of 9 cm, and 10 third-instar larvae of diamondback moth 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. The number of live and dead insects was investigated 4 days after the treatment and release, and the death rate was calculated. The results are shown in Table 2 as the average value of duplicates. As for this diamondback moth, a product from Ageo and a product from Kagoshima, which is resistant to organophosphorus agents, carbamate agents, pyrethroid agents and the like, were used.

[0052]

[0053]

Test Example 2. Effect on Spodoptera litura A 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: The middle leaf of cabbage grown to about 10 cabbage true leaves was cut off, diluted with water so that the active ingredient of each reagent was 200 ppm, and the solution was treated with 2
It was immersed for 0 seconds. After air-drying, two treated leaves were placed in a plastic container having a diameter of 9 cm, and 5 third-instar larvae of Spodoptera litura were released into the container. The container was covered with a lid having 5 to 6 small holes and allowed to stand in a constant temperature room at 25 ° C. The number of live and dead insects was investigated 4 days after the treatment and release, and the death rate was calculated. The results are shown in Table 3 as an average value of triplicates.

[0056]

Test Example 3. Effect on Cobb Noumea 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 trifoliate rice grains were added to the treatment liquid diluted with water so that the active ingredient of each reagent was 200 ppm.
Soaked for seconds. After air-drying, the rice was wrapped with urethane and fixed in a glass cylinder (inner diameter 44 mm, height 140 mm), and 5 third instar insects of Cobbnomaiga were released, and the upper part of the glass cylinder was covered with a medicine wrapping paper. The glass cylinder was allowed to stand in a constant temperature room at 25 ° C. for 16 hours in the light period. The number of live and dead insects was investigated 4 days after the treatment and release, and the death rate was calculated. In addition, the test was conducted in a double system, and Cobno meiga used the acceptability line. The results are shown in Table 4.

[0058]

Test Example 4. Results for Spodoptera litura Foliar 20% wettable powder or 20% emulsion of the compound of the present invention was prepared 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 in a treatment liquid diluted with water so that the active ingredient of the reagent was 200 ppm for 20 seconds. After air-drying, plastic container (inner diameter 7
0 mm, height 40 mm)
Five instars were released. The container was covered with a lid having 5 to 6 small holes and allowed to stand in a constant temperature room at 25 ° C. for 16 hours in the light period. The number of live and dead insects was investigated 4 days after the treatment and release, and the death rate was calculated. In addition, the test was conducted in a double-consecutive manner, and the susceptibility strain was used as the tea squirrel. The fifth result
Shown in the table.

[0060]

[0061]

Since the present invention is configured as described above with reference to the embodiments, it has the following effects. N, N'-dibenzoyl-tert- of the present invention
The butylhydrazine derivative has an excellent insecticidal effect against harmful insects which are resistant to known insecticides such as organic phosphorus agents and pyrethroids, and is a pest control scene in paddy fields, uplands, orchards, forests or environmental hygiene scenes. Is effective in.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Office reference number FI technical display location C07C 255/57 8519-4H C07D 317/62 7729-4C 319/08 7729-4C (72) Inventor Kazuo Asahina 2-13-4 Nakamachi, Ageo-shi, Saitama 311 Forstheim 311 (72) Inventor Mikio Yanagi 4265-3 Kawataya, Okegawa, Saitama

Claims (2)

[Claims] 1. A general formula: [Wherein R ¹ , R ² , R ³ and R ⁴ are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, or (C ₁ -C _1
4 ) alkyl group, (C ₁ -C ₄ ) haloalkyl group, (C
₂ -C ₄₎ alkenyl group, (C ₂ -C ₄₎ alkynyl, (C ₁ -C ₄₎ alkoxy, (C ₁ -C ₄₎ haloalkoxy group (two adjacent positions alkoxy groups, haloalkoxy When substituted with a group, these substituents may be bonded to form a 5-membered or 6-membered dioxolano or dioxano ring, and R ⁵ is (C _1- ).
C ₄₎ alkyl group, a (C ₂ ~C ₄₎ alkenyl group, R ⁶ is a hydrogen atom, (C ₁ ~C ₄₎ alkyl group, (C
_{2 to} C ₄ ) alkenyl, (C _{2 to} C ₄ ) alkynyl group], or an N, N′-dibenzoyl-tert-butylhydrazine derivative. 2. An insecticidal composition comprising an N, N′-dibenzoyl-tert-butylhydrazine derivative represented by the general formula (1) according to claim (1) as an active ingredient.