JP2823376B2 - Phenylthiourea derivative and insecticidal and acaricidal composition containing the same as an active ingredient - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel phenylthiourea derivative which can be used as an insecticide or acaricide.

[0002]

2. Description of the Related Art A substituted phenylthiourea compound is disclosed in JP-A-53-31645 and JP-A-56-81558.
Discloses that substituted phenoxyphenylthiourea compounds are useful as insect control agents.
E-230620 describes that substituted phenylisothiourea compounds are useful, and JP-B-63-52627 describes that substituted phenoxyphenylisothiourea compounds are similarly useful as insect-controlling agents.

[0003]

However, these compounds are not always sufficient in insecticidal activity or safety. In addition, conventional insecticides such as organic phosphorus agents and carbamates have developed resistance to pests and have become difficult to control, and new types of agents have been desired.

[0004]

Means for Solving the Problems The present inventor has conducted intensive studies in order to solve the above-mentioned problems, and as a result of the general formula

[0005]

[Wherein R ¹ and R ² each independently represent a lower alkyl group, a C ₃ -C ₆ cycloalkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfenyl group or a lower alkoxycarbonyl group; , R ³ represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or an alkoxy group which may be substituted with a lower alkoxycarbonyl group, R ⁴ represents a lower alkyl group or a lower cycloalkyl group, and Z is- NH
CSNH- or -N = C (SR ⁵⁾ -NH- with a group represented, and R ⁵ represents a lower alkyl group or an allyl group. ] The phenylthiourea derivative represented by the formula (1) has an extremely high insecticidal and acaricidal effect, and the present invention has been completed.

The compound of the general formula (1) of the present invention can be produced by the following method. First, in the general formula (1), a thiourea compound represented by Z = —NHCSNH—

[0008]

Wherein R ¹ , R ² , R ³ and R ⁴ have the same meaning as described above. Is the general formula

[0010]

Wherein R ¹ , R ² and R ³ have the same meaning as described above. And an isothiocyanate represented by the general formula

H ₂ NR ⁴ (3)

Wherein R ⁴ has the same meaning as described above. ]
By reacting an amine represented by The reaction is carried out in an equimolar ratio or in an approximately equimolar ratio, but either component can be used in a large excess. Preferably, the amine of the general formula (3) is used in a large excess, i.e. in an amount of from 2 to 20 mol, per mol of the isothiocyanate of the general formula (2). The reaction can be carried out in the absence of a solvent or in the presence of a solvent inert to the reactants.

Examples of the solvent include aliphatic hydrocarbons such as hexane, heptane and petroleum benzine; aromatic hydrocarbons such as benzene, toluene and xylene; chloroform;
Halogenated hydrocarbons such as dichloromethane and chlorobenzene, ethers such as diethyl ether and tetrahydrofuran, acetonitrile, nitriles such as propionitrile, esters such as ethyl acetate, acetone,
Ketones such as methyl ethyl ketone, non-proton-donating polar solvents such as dimethylformamide and dimethyl sulfoxide, alcohols such as methanol and ethanol,
Or a mixed solvent thereof. The reaction temperature ranges from 0 ° C to 150 ° C, preferably from 10 ° C to 80 ° C. Next, in the general formula (1), Z = −N = C (S
R ⁵ ) —An isothiourea compound represented by —NH—

[0015]

Wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵
Has the same meaning as described above. ] Represents a thiourea compound represented by the general formula (1) a

R ⁵ -Hal (4)

[Wherein R ⁵ has the same meaning as described above;
l represents a halogen atom. With a halide represented by the formula (I) in the presence or absence of a suitable base (deoxidizing agent).

Suitable bases (deoxidizing agents) include, for example, alkali metal hydroxides (NaOH, KOH, etc.), alkaline earth metal hydroxides (Ca (OH) _2, Mg (OH) _2, etc.), and alkali hydroxides. Metals, alkyl lithium reagents, alkali metal alcoholates (such as sodium alcoholate), alkali metal oxides (such as Na ₂ O, K ₂ O),
Aliphatic and aromatic tertiary compounds such as alkali metal carbonates (such as soda ash), alkali metal amides (such as sodium amide), triethylamine, dialkylaniline, and pyridine
Grade amines and the like.

The reaction is usually carried out in an approximately equimolar ratio in the presence of an inert solvent, but it can also be carried out using either component in excess. Examples of the inert solvent include the above-mentioned solvents that can be used for obtaining the thiourea compound represented by the general formula (1) a. The reaction temperature is 0 ° C to 15
0 ° C., preferably in the range of 20 ° C. to 100 ° C. The isothiourea compound represented by the above formula (1) b has the following formula

[0021]

And tautomers thereof. The present invention includes the individual tautomers as well as mixtures of tautomers. To isolate the desired product from the reaction mixture obtained as described above, the solvent is distilled off under reduced pressure, or the reaction mixture is extracted with an organic solvent such as methylene chloride, chloroform, ethyl acetate or toluene. After washing and drying, the organic solvent may be simply distilled off under reduced pressure, if necessary. Further, if necessary, purification is carried out by recrystallization or column chromatography.

In the general formula (1) of the present invention, examples of the lower alkyl group include methyl, ethyl, n-propyl,
iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-amyl, sec-amyl, tert
-Amyl and n-hexyl groups.
Examples of the C ₃ -C ₆ cycloalkyl group include a cyclopropyl, cyclopentyl, cyclohexyl group and the like. Examples of the lower alkoxy group include methoxy, ethoxy, n-propoxy, iso-propoxy,
Examples include various butoxy groups. Examples of the lower alkylthio group include methylthio, ethylthio, n
-Propylthio, isopropylthio, n-butylthio,
Iso-butylthio, sec-butylthio, tert-butylthio groups and the like. Examples of the alkoxy group optionally substituted with an alkoxycarbonyl group include a methoxycarbonylmethoxy group and an ethoxycarbonylmethoxy group.

The lower alkylsulfenyl group includes, for example, methylsulfenyl, ethylsulfenyl, n-propylsulfenyl, iso-propylsulfenyl and the like. Examples of the alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, iso-butoxycarbonyl, sec-butoxycarbonyl, and tert-butoxycarbonyl group.

When the compound of the general formula (1) of the present invention is used, it is generally used in the field of agrochemical production according to the purpose of use, either as it is or by mixing an agrochemical adjuvant to promote or stabilize the effect. Depending on the method, powders, fine granules, granules, wettable powders, flowables, emulsions, microcapsules, oils, aerosols, fumigants such as fumigants (mosquito coils, electric mosquito coils, etc.), fogging, etc. , Unheated fumigants, bait and the like, and can be used as a composition in any pharmaceutical form.

In the actual use, 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. Examples of the liquid carrier include aromatic hydrocarbons such as toluene and xylene, butanol, octanol, alcohols such as glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethylsulfoxide, methylnaphthalene, cyclohexanone, Examples include animal and vegetable oils, fatty acids, fatty acid esters and the like, as well as petroleum fractions such as kerosene and light oil, and water. Examples of the solid carrier include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, 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. , Nonionic surfactants and zwitterionic surfactants.

Examples of the spreading agent include polyoxyethylene nonyl phenyl ether and polyoxyethylene lauryl ether, and examples of the wetting agent include polyoxyethylene nonyl phenyl ether and dialkyl sulfosuccinate. Examples thereof include carboxymethyl cellulose and 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. Other physiologically active substances such as arelesrin, phthalthrin, permethrin, decamesulin, fenvalerate, Pyrethroids and various isomers such as cycloprothrin, pyrethrum extract, organophosphorus pesticides such as DDVP, fenitrothion, diazinon, and temefos; carbamate pesticides such as NAC, MTMC, BPMC and pyrimer; other pesticides; Or fungicide, nematicide, herbicide, plant growth regulator, fertilizer, B
By mixing with T agents, insect hormonal agents and other pesticides, a multipurpose composition with even better efficacy can be produced, and a surplus effect can be expected.

If necessary, an antioxidant or an ultraviolet absorber, for example, a phenol such as BHT or BHA, an arylamine such as α-naphthylamine, or a benzophenone-based compound may be appropriately added to stabilize the effect. The resulting composition can be obtained. The content of the active ingredient in the composition of the present invention varies depending on the form of the preparation, the method of application and other conditions, and in some cases, the active ingredient compound alone may be used. % (Weight).

The amount of the composition of the present invention varies depending on the dosage form, method of application, timing, and other conditions. Agricultural and horticultural agents, forest pest agents and pastoral insect pests usually contain an active ingredient per 10 ares. 10 to 300 g, preferably 15 to 20
0 g is used, and the amount of the active ingredient for the sanitary insect pest is usually ² to 200 mg, preferably 5 to 100 mg, per m ² . For example, dust is 1 active ingredient per 10 ares.
The amount of the active ingredient ranges from 30 to 240 g, and that of the emulsion and the wettable powder ranges from 40 to 250 g. However, in special cases, it is possible, and sometimes even necessary, to exceed or fall below these ranges.

Specific pest names to which the insecticidal and acaricidal composition of the present invention can be applied are listed. From the order of the Hemiptera, for example, the leafhopper leafhopper (Nephotettix cincti-ceps)
, Japanese brown planthopper (Sogatella furcifera), brown planthopper (Nilaparv-ata lugens), brown planthopper (L
aodelphax striatellus), Rabbit bug (Riptort)
us clavatus), southern stink bug (Nezara viridul)
a), Stephanitis nashi, Trifolius vaporario-rum, Cotton aphid (Aphis gossypii), Peach aphid (Myz)
us pers-icae), the wild scale insect (Unaspis yanon)
ensis), lepidoptera (Lepidoptera) and, for example, Phyllonorycter ringoneella,
t-ella xylostella), cotton moth (Promalactis inonise)
ma), Kamakumamakimaki (Adoxophyes orana), Mameshinguiga (Leguminivora glycinivorella), Coleoptera (Cnaphalocrocis medinalis),

[0032] The Japanese squid (Chilo suppressalis), the Japanese squid (Ostrinia furnacalis) and the armyworm (Mame)
stra brassicae), armyworm (Pseudaletia separat)
a), Lotus armyworm (Spodoptera litura), rice beetle (Parnara guttata), cabbage butterfly (Pieris)
rapae crucivora), Heliothis (Heliothis spp.), Noctuid (Agrotis spp.), Coleoptera, for example, Anagala cuprea, Popillia japonica, and Echi-nocnem
us squameus), rice weevil (Lissorhoptrus ory)
zophilus), rice dwarf beetle (Oulemaoryzae), Japanese beetle beetle (Anthrenus verbas-ci), coconut (Tenebroides mauritanicus), coccinellidae (S
itophiluszeamais) and the Japanese ladybird (Henose
pilachna vigintioctopunctata), Adzuki beetle (Ca
llosobruchus chinensis), pine beetle (Mo)
no-chamus alternatus), beetle beetle (Aulacophora fe)
moralis), Leptinotarsa desemlineata (Leptin
otarsa decemlineata),

Phedon cocariae (Phaedon coc)
hleariae), Diabro-tica spp., Hymenoptera, for example,
thaliarosae japonensis), Rurichu range wasp (Arge similis), diptera (Di-ptera) such as Aedes aegypti (Culex pipiens fatigans), Aedes aegypti, and soybean flies (A
sphondylia sp.), fly (Hylemya platura), housefly (Musca domestica vicina), seafly (Dac)
us cucurbitae), rice leaf fly (Agromyza oryza)
e), Flies (Lu-cilia spp.),

[0034] Human fleas (Pulex irritana) and Coleoptera flea (Xenopsyll) as Aphaniptera
a cheopis), dog flea (Ctenocephaides canis), Thrips palmi (Scirtothrips dorsalis), and thrips (Thrip) as Th-ysanoptera
s tabaci), Thrips palmi (Thrips palm)
i), rice thrips (Baliothrips biformis), as lice (Anoplura), for example, white lice (Pedi)
culus humanus corporis), psyllium (Pthirus pubis)
, As the order Psocoptera, for example, Trogiumpulsatorium,

Hirata chatate (Liposcelis bostrychop)
ilus), as a Orthoptera (Gryllota)
lpa africana), Tonosama grasshopper (Locusta migrator)
ia), Red-bellied locust (Oxya yezonesis), German cockroach (Blattella germanica), Black cockroach (Peripl)
aneta fuliginosa), Isoptera, Reticulitermes speratus, Coptotermes fo-rmosanus, Acarina
As, for example, spider mites (Tetranychusurticae),
Red mite (Panonychus citri), Red mite (Tetranychuscinnabarinus), Red mite (Tetr)
anychus kanzawai), Apple spider mite (Panonychus ulmi)
, Red spider mite (Tetranychus viennensis), citrus red mite (Aculops pelekassi), Dermatophagoid mite (Polyphagotarsonemus latus),
onychus hondoensis) and the pear mite (Epitrimerus py)
-ri), Cyclamen dust mite (Steneotarsonemus pal)
lidus), Japanese red mite (Tenuipalpus zhizhilashvi)
liae), Red-bellied spider mite (Brevipalpus obovat-us)
, Clover spider mite (Bryobia praetiosa), grape rust mite (Calepitrim-erus vitis), Tyrophagus mite (Tyrophagus putrescenticae), spider mite (Rh-izogly)
phus echinopus), ox tick (Boophilus spp.),
Red tick (Rhipicephalus spp.), Ambrioma (Amblyomma spp.), Tick (Ixodex spp.).

[0036]

Industrial Applicability The phenylthiourea derivative of the present invention has excellent insecticidal activity against pests that have acquired resistance to organophosphorus agents, carbamates, etc., and also has excellent acaricidal activity against mites. Have.

[0037]

The present invention will be described below with reference to examples.
The present invention is not limited only to these. Production Example 1 N- (2,5-di-tert-butylphenyl) -N'-te
rt-Butylthiourea (Compound No. 1): To a solution of 3.2 g (13 mmol) of 2,5-di-tert-butylphenylisothiocyanate in 40 ml of toluene, 2.9 g (39 mmol) of tert-butylamine at room temperature. Was added and reacted at 50 ° C. for 5 hours.

The residue obtained by evaporating the solvent under reduced pressure is purified by silica gel column chromatography and then crystallized to give N- (2,5-di-tert-butylphenyl) -N'-tert. 3.5 g (yield 84.5%) of -butylthiourea was obtained. m. p. 130-131 ° C

Production Example 2 N- (5-tert-butyl-2-iso-propylphenyl) -N'-tert-butylthiourea (Compound No. 1)
0): 5-tert-butyl-2-is is added to a solution of 2.0 ml (19.3 mmol) of tert-butylamine in methylene chloride (30 ml).
o-Propylphenyl isothiocyanate 1.5 g
(6.4 mmol was added at room temperature, and the mixture was heated under reflux for 5 hours. After cooling, the reaction solution was poured into water and extracted with methylene chloride. The organic layer was dried over sodium sulfate, and methylene chloride was distilled off. The residue obtained was purified by silica gel column chromatography.

Thereafter, by crystallization, N- (2-
tert-butyl-5-iso-propylphenyl) -N'-
2.0 g (89% yield) of tert-butylthiourea was obtained. m. p. 127-128 ° C

Production Example 3 N- (2,5-tert-butylphenyl) -N'-tert-
Butyl-S-methylisothiourea (Compound No. 2
1): N- (2,5-di-tert-butylphenyl) -N′-te
1.56 g (4.9 mmol) of rt-butylthiourea was dissolved in 10 ml of N, N-dimethylformamide, and 96%
1.1 g (7.4 mmol) of methyl iodide was added dropwise at room temperature. After further stirring at room temperature for 3 hours, the reaction solution was added for 5 hours.
% Aqueous sodium carbonate and the solution was extracted with ethyl acetate.

The organic layer was washed with water and sodium sulfate (anhydrous)
After drying with ethyl acetate, the residue obtained by evaporating ethyl acetate was purified by silica gel column chromatography to give N-
(2,5-di-tert-butylphenyl) -N′-tert-
1.5 g of butyl-S-methylisothiourea (yield 9
2.1%). Refractive index (25 ° C) 1.5400

Production Example 4 N- (4-chloro-2,5-di-tert-butylphenyl) -N'-tert-butyl-S-methylisothiourea (Compound No. 24): N- (4-chloro) 1.39 g of (-2,5-di-tert-butylphenyl) -N'-tert-butylthiourea (3.
(9 mmol) was dissolved in 10 ml of N, N-dimethylformamide, and 0.9 g (5.9 mmol) of 96% methyl iodide and 0.54 g (3.9 mmol) of anhydrous potassium carbonate were added at room temperature. After further stirring at room temperature for 2 hours,
The reaction solution was poured into ice water, and the solution was extracted with ethyl acetate. After the organic layer was washed with water and dried over anhydrous sodium sulfate, the residue obtained by distilling off ethyl acetate was purified by silica gel column chromatography to give N- (4-chloro-2,5-di-tert- Butylphenyl) -N'-tert-
1.4 g of butyl-S-methylisothiourea (yield 9
7.0%).

Refractive index (25 ° C.) 1.5448 Tables 1 and 2 show typical examples of the compounds of the present invention, including the above Examples.

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

(In Tables 1 and 2, a ₁ = C (C
_{H 3) 3, a 2 =} CH (CH 3) 2, a 3 = cyclopropyl group, a ₄ = _{cyclohexyl, a 5 = 3-C (} C
H ₃ ) ₃ , a ₆ ＣC (CH ₃ ) ₂ C ₂ H ₅ , * = Refractive index preparation example)

Formulation Example 1 Emulsion 65 parts of a mixture of xylene-methylnaphthalene was added to and dissolved in 20 parts of the compound of Compound No. 8, and then 15 parts of a mixture of alkylphenol ethylene oxide condensate and calcium alkylbenzenesulfonate (8: 2) were mixed. An emulsion was prepared. The drug is diluted with water and used as a spray liquid.

Formulation Example 2 Wettable powder 35 parts of kaolin, 30 parts of clay, and 7.5 parts of diatomaceous earth are mixed with 20 parts of compound No. 1 and 7.5 parts of a mixture (1: 1) of sodium laurate and sodium dinaphthylmethanesulfonate. Was mixed and pulverized to obtain a powder.
The drug is diluted with water and used as a spray liquid.

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

Formulation Example 4 Granules 2 parts of the compound of Compound No. 2 were 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 and 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 agent 0.5 part of piperonyl butoxide was added to 0.1 part of compound No. 6 and dissolved in white kerosene to make the whole 100 parts to obtain an oil agent. Use this drug as is.

Formulation Example 6 Aerosol 0.4 part of the compound of compound No. 6, 20 parts of piperonyl butoxide, 6 parts of xylene, 7.6 parts of deodorized kerosene are mixed and dissolved, filled into an aerosol container, and a valve part is attached. 86 parts of Freon was filled under pressure to obtain an aerosol. Formulation Example 7. Heated fiber-fumigated insect composition Dissolve 0.05 g of compound No. 1 in an appropriate amount of chloroform and evenly adsorb to the surface of asbestos of 2.5 cm × 1.5 cm thickness 0.3 mm and heat-fumigated insects on a hot plate A composition was obtained.

Formulation Example 8 Mosquito coil: 0.5 g of compound No. 5 is dissolved in 20 ml of methanol, and a carrier for incense sticks (tab flour: lees flour: wood flour 3: 5: 1)
Was mixed uniformly with 99.5 g, and methanol was evaporated. Then, 150 ml of water was added, and the mixture was sufficiently kneaded to obtain a mosquito coil. Next, the effects of the present invention will be specifically described with reference to test examples.

Test Example 1 Effect on brown planthopper 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. BPMC 50% emulsion and diazinon 40% emulsion were used as control drugs.

Test method: Eight rice plants in the 3-4 leaf stage were 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, put into a glass cylinder of 4.5 cm in diameter and 15 cm in height. 10 larvae of the third-instar larvae of brown planthopper (Kayada) susceptible to this and susceptible to both organic phosphorus and carbamate And cover it with a wire mesh lid,
It was left still in a constant temperature room at 25 ° C. Six days after the treatment, the live and dead insect rates were investigated, and the dead insect rates were calculated. The result is the average of duplicates and the third
It is shown in the table.

[0061]

* Compound A: (Compounds described in JP-A-53-31645)

Test Example 2 Effect on Conaga 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. MEP 50% emulsion and cypermethrin 6% emulsion were used as control drugs.

Test method: The middle leaves of cabbage grown to about 10 cabbage leaves were cut off, and treated with a treatment solution diluted with water so that the active ingredient of each reagent was 200 ppm.
Dipped for 0 seconds. After air-drying, it was placed in a 9 cm-diameter plastic container, and 10 larvae of the 3rd instar were released. The container was covered with a lid having 5 or 6 small holes, and allowed to stand in a constant 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 4 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.

[0066]

Test Example 3 Effect on Lotus armyworm 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 leaf of cabbage grown to about 10 cabbage leaves was cut off, and treated with a treatment solution diluted with water so that the active ingredient of each reagent was 200 ppm.
Dipped for 0 seconds. After air drying, put 2 treated leaves in a 9cm diameter plastic container,

Five third-instar larvae of Spodoptera litura were released into a container. Cover the container with 5 or 6 small holes and cover with 2
It was left still in a constant temperature room at 5 ° 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 5 as an average of triplicates.

[0070]

* Compound B; (Compounds described in DE-2730620)

Test Example 4 Effect on adult spider mite, Tetranychus kanzaii 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. A fenbutatin oxide 25% wettable powder was used as a control drug.

Test Method: The primary leaves of kidney beans planted in a 6 cm diameter unglazed pot were shaped into a size of about 3 cm × 3 cm, and 15 adult female spider mites were inoculated on each leaf. 24 hours at 25 ° C
After leaving still in a greenhouse, dead insects and unhealthy insects were removed, and the resultant was immersed for 10 seconds in a treatment solution diluted with water so that the active ingredient of each reagent agent was 200 ppm.

48 hours after the treatment, the number of live and dead spider mites was examined, and the mortality was calculated. The results are shown in Table 6. In addition,
The spider mites used were susceptible strains from Sapporo and resistant strains from Aomori.

[0075]

Test Example 5 Effect on termites A 20% wettable powder or a 20% emulsion of the compound of the present invention was produced according to Production Examples 1 and 2, and used as a reagent. Chlorpyrifos 25% wettable powder was used as a control drug.

Test method: The active ingredient of each reagent was 200
1 ml of the treatment solution diluted to a ppm was applied to a filter paper having a diameter of 9 cm. The filter paper was placed in a plastic Petri dish, and ten house termites and one soldier were released. One day after releasing the insects, the life and death of the ant was investigated, and the mortality was calculated. The results are shown in Table 7 as the average of duplicates.

[0078]

Continuation of the front page (58) Field surveyed (Int. Cl. ⁶ , DB name) C07C 335/16 A01N 47/30 A01N 47/42 C07C 335/36 CA (STN)

Claims (2)

(57) [Claims] (1) General formula [Wherein R ¹ and R ² each independently represent a lower alkyl group, C ₃ -C ₆ cycloalkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfenyl group, or a lower alkoxycarbonyl group, R ³ Represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy group which may be substituted with a halogen atom or an alkoxycarbonyl group, R ⁴ represents a lower alkyl group or a cycloalkyl group, and Z represents -NHCSNH- or-.
N = C (SR ⁵⁾ indicates -NH-, a group represented by and R ⁵ represents a lower alkyl group or an allyl group. ] The phenylthiourea derivative represented by these. 2. An insecticidal and acaricidal composition comprising the thiourea derivative represented by the general formula (1) according to claim 1 as an active ingredient.