JPS60158162A - Methanesulfonate derivative and insecticidal composition containing same as active constituent - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (R<1> is H, Cl or methyl; R<2> is halogen-substituted lower alkyl and lower alkenyl, etc.; X is 0, 1 or 2). EXAMPLE:3-[n-(3'-Fluoropropyl)thio]phenylmethanesulfonate. USE:An insecticide without giving phytotoxicity to useful crops including rice plants. PREPARATION:A compound expressed by formula II (Y is H, alkali or alkaline earth metal) is reacted with a methanesulfonyl halide or methanesulfonic acid anhydride or a compound expressed by formula II (X is 0) is reacted with the methanesulfonyl halide or methanesulfonic acid anhydride to afford the aimed compound expressed by formula I (X is 0), which is oxidized with an oxidizing agent to give the compounds expressed by formula I (X is 1 and 2).

Description

Detailed Description of the Invention The present invention is based on the formula (wherein J" represents a hydrogen atom, a chlorine atom, or a methyl group, and R2 is a lower alkyl group substituted with a halogen atom, a lower alkenyl group substituted with a halogen atom, or a halogen atom). represents a cyclopropylmethyl group substituted with an atom,
represents 0.1 or 2. ) and an insecticidal composition containing the derivative as an active ingredient.

In recent years, important pests of paddy rice, such as the black leafhopper and brown planthopper, have begun to show resistance to organic phosphates, carbamates, and methanesulfonate compounds, which are conventionally widely used insecticides. Ta.

Therefore, how to control these resistant pests has become a major problem, especially in rice-growing areas. Surprisingly, the compounds of the present invention are significantly more effective against both susceptible and resistant insect pest systems than conventional organophosphate agents, carbamate agents, and even the methanesulfonate derivatives of Japanese Patent Publication No. 43-3898 and Japanese Patent Publication No. 48-98025. It was found to have high insecticidal oiliness. On the other hand, it has been found that the compound of the present invention has little phytotoxicity against various useful crops including rice, and is also a practical insecticide.

(In the formula, R2 and X each have the above meanings, and Y represents a hydrogen atom or an alkali or alkaline earth metal atom.

A compound represented by methanesulfonic acid or anhydride is reacted with methanesulfonic acid or anhydride, or a compound of formula (I) with x = O is reacted with methanesulfonyl halide or methanesulfonic anhydride, and a compound of the formula (Il with x = O Synthesize the compound x using an oxidizing agent
= 1 and x = 2 can be synthesized.

That is, when reacting the phenol derivative of formula (2) (when Y is a hydrogen atom in formula (III)) with methanesulfonyl halide or methanesulfonic anhydride, - 10℃~
The desired methanesulfonate derivative can be obtained by reacting at 100°C, preferably 0°C to 40°C for 0.5 to 10 hours. The bases mentioned here include, for example, alkali metal hydroxides (NaOH, KOH, etc.), hydroxides 7
/l/potassic earth metal (Ca (OH)29Mg (O
H)2, etc.) Alkali metal hydrides, alkali metal alcolades (sodium alcolades, etc.) alkali metal oxides (Na2O, K20, etc.) alkali metal carbonates (soda ash, etc.), sodium amide, triethylamine,
Examples include aliphatic and aromatic tertiary amines such as dialkylaniline and pyridine.

Silver oxide can also be used as the acid binder.

In addition, solvents include water, aromatic hydrocarbons such as benzene, toluene, and xylene, aliphatic hydrocarbons such as hexane, heptane, and petroleum benzene, halogenated hydrocarbons such as chloroform and dichloromethane, and non-containing solvents such as dimethylformamide and dimethyl sulfoxide. Proton-donating polar solvents, lower alcohols such as methanol and ethanol, diisopropyl ether, diethyl ether, 1,
Ethers such as 2-dimethoxyethane, tetrahydrofuran and dioxane, nitriles such as acetonitrile and propionitrile, acetone, diisopropyl ketone,
Ketones such as methyl ethyl ketone can be used. Furthermore, the desired methanesulfonate derivative can be obtained in good yield by using a phase transfer catalyst such as tetra-n-butyl-ammonium bromide or triethylbenzylammonium chloride as a catalyst. When reacting the phenoxyto derivative of formula I (where Y is an alkali or alkaline earth metal atom in formula I) with methanesulfonyl chloride, the reaction temperature is 10°C to 100°C, preferably 0°C to 40°C, in the above solvent. The desired methanesulfonate derivative can be obtained in good yield by reacting at a temperature of 0.5 to 5 hours.

Compounds with x = 1 or 2 in Wenmu (11) can be obtained by obtaining the x = 00 compound by the method described above and then treating it with an oxidizing agent such as hydrogen peroxide, i.e. 1.0-2. When reacted in acetic acid containing .0 times the mole of hydrogen peroxide at 0°C to 30°C for 3 to 5 hours, x =
1 can be obtained, and when reacted in acetic acid containing 2.0 to 3.0 times the mole of hydrogen peroxide at 0°C to 100°C, preferably at 60°C to 100°C for 3 to 5 hours. x =
Compound 2 can be obtained in good yield.

In the compound of the formula (Jl) of the present invention, examples of the lower alkyl group substituted with a halogen atom include a methyl group, an ethyl group, an n-propyl group, an isobutyl group, and an n-butyl group substituted with a fluorine, chlorine, or bromine atom. Examples of lower alkenyl groups substituted with halogen atoms include allyl groups or butenyl groups substituted with fluorine, chlorine, or bromine atoms. Examples of the substituted cyclopropylmethyl group include a cyclopropylmethyl group substituted with two fluorine, chlorine, or bromine atoms.

In addition to hydrogen peroxide, the oxidizing agent for x = 1 in the compound of x = Q in formula (11) includes organic peroxides, halides, periodates, nitrogen oxides, ozone, metal oxides, - It includes heavy ring oxygen and can also be obtained by air oxidation and anodic oxidation.

In addition to hydrogen peroxide, as an oxidizing agent for converting the compound of x = Q or x = l to the compound of X = 2 in formula (11),
peracid, hydroperoxide, halogen, halogenating agent,
Ozone, oxygen and transition metal catalysts, potassium peroxysulfate, potassium permanganate, dinitrogen tetroxide, sodium metaperiodate, osmium oxide (■ valence), ruthenium oxide (■ valence), sodium dichromate, nitric acid, etc. can be,
Oxidation using electrodes is also possible.

When the starting phenol derivative of formula I is X--O, the phenol derivative of formula I can be prepared using known methods (for example, Japanese Patent Publication No.
87), and the phenol derivatives with the formula l where x = l and x = 2 can be easily oxidized by oxidizing the phenol derivative where x = O with the above-mentioned oxidizing agent under similar conditions. Moreover, it is produced with good yield.

Next, the method for producing the novel methanesulfonate derivative of the present invention will be described in more detail with reference to Examples.

Example 1. Synthesis of 3-(n-(3'-fluoropropyl)thio]phenylmethanesulfonate (compound N[L21) 3-(n-(3'-fluoropropyl)thio]phenol 7.4f, methanesulfonyl chloride 4.6 Cool 40 ml of a solution of P in ether to below 5°C. Add 4.0 ml of triethylamine dropwise over 10 minutes while stirring. Then, continue stirring at room temperature for 5 hours and pour into 100 ml of water. Add 5% caustic soda to the ether layer. The solution was washed with 5% hydrochloric acid and water, dried over anhydrous sodium sulfate, the solvent was distilled off, and the resulting residue was vacuum distilled to obtain the desired 3-[n-
(3'-Fluoropropyl)thio]phenylmethanesulfonate 10.07 was obtained as a pale yellow oil. Yield 95
%.

bp193~194°G/3 mmHg 0 elemental analysis value CIOHI3 FOa Calculated value as S 2 C
:45.44:H:4.96 Actual value C:45.41:
H: 5.00 Example 2. Synthesis of 3-[n-(3'-fluoropropyl)s,Q/finyl]phenylmethanesulfonate (compound N22) 3-(: n-(3'-fluoropropyl)thio]phenylmethane obtained in Example 1 Dissolve sulfonate 3.51 in 20 rnl of methanol and cool to 0°C. Add dropwise a solution of sodium periodate 4.31 in 20 ml of water. Then stir at room temperature for 5 hours and pour into water. Extract with methylene chloride. and dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent was purified by silica gel column chromatography (developing solvent: ethyl acetate-ether 4:1). fluoropropyl)
sulfinyl phenylmethane sulfone) 2.69
This was obtained as a yellow oil. Yield 73% On, g51
．． 5407゜Elemental analysis value C8゜H+a Calculated value as FO482 C:42.84:H:4.67 Actual value C
:42.83:H:4.70 Example 3. 3-(n-(
Synthesis of 3-fluoropropyl)sulfonyl]phenylmethanesulfonate (compound Nn23) 3.21 of 3-[n-(3-fluoropropyl)thio]phenylmethanesulfonate obtained in Example 1 was added to 15 #l of acetic acid.
1, and add 35% hydrogen peroxide solution 6.6 to this at room temperature.
Drop ml. Thereafter, the mixture was stirred at 80-90°C for 1.5 hours, cooled, and then poured into water. After extraction with methylene chloride, the organic layer was washed with 5% caustic soda solution, 5% aqueous hydrochloric acid, and water, and dried over sodium sulfate. - Hexane l:1) to purify the desired 3-(
n-(3-fluoropropyl)sulfonyl]phenylmethanesulfonate 3.469- was obtained as a pale yellow oil. Yield 96.4% on J, 5233° elemental analysis value
Calculated value as C1o H+3F Os S 2 C:4
0.53:H:4.42 Actual value C:40°53;I
-I: 4.39 Example 4. Synthesis of 3-CC2,2-dichloropropyl)methylsulfinyl]phenylmethanesulfonate (compound IV4IL17) 3-[(2
,2-dichlorocyclopropylenemethylsulfinyl]
2.6 g of phenol was dissolved in 10 ml of 30% caustic soda, and 0.0 g of triethylbenzylammonium chloride was added thereto. Add IP, cool to below 5°C, and remove 1.7P of methanesulfonyl chloride. The reaction is then completed by stirring at room temperature for 2 hours. Extract the contents with methylene chloride,
After washing with 5% caustic soda solution, 5% aqueous hydrochloric acid, and water and drying over anhydrous sodium sulfate, the solvent was distilled off and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate-ether 4:1). The targeted 3-[(2,
2.71 of 2-dichlorocyclopropyl]methylsulfinyl]phenylmethanesulfonate was obtained as a pale yellow oil. Yield 78.7%011D1.5589゜Elemental analysis value CIIHI□CI204 Calculated value as S2 C: 38.49; H: 3.53 Actual value C:
38.45; H: 3.55 Example 5. 3-[n-
Synthesis of (3'-bromopropyl)sulfonyl-4-methylphenylmethanesulfonate (compound N125) 3-(n-(3-bromopropyl)sulfonyl-4-
Methylphenol 2.95” 1r95% caustic soda 0
．． Change 10 to a solution of 51 dissolved in methanol 10a6
Stir for a minute. After distilling off the solvent, 10 ml of N,N-dimethylacetamide was added and stirred for 10 minutes.

Next, this was cooled to 10° C. or lower, 1.7 P of methanesulfonyl chloride was added, the temperature was returned to room temperature, and the mixture was stirred for 2 hours to complete the reaction. The contents were extracted with methylene chloride, washed with 5% caustic soda solution, 5% aqueous hydrochloric acid, and water, and dried over anhydrous sodium sulfate. The solvent was distilled off and the resulting residue was subjected to silica gel chromatography (developing solvent: The desired product 3-[n-(3-bromopropyl)sulfonyl]-4-methylphenylmethanesulfone) 2.951- was obtained as a pale yellow oil.

Yield 78.1%. n, 61.5502゜Elemental analysis value C
Calculated value as 1+ ILs Br Os 82 C:
35.59: H: 4.07 Actual value C: 35.
62:H: 4.07 Further compounds of the present invention were synthesized by the methods of Examples 1 to 5. Representative ones are shown in Table 1.

Next, specific insect pests to which the insecticidal and acaricidal composition of the present invention can be applied are listed.

From Hem1ptera, for example, Nephotettix cinctice
ps), white-legged planthopper (Sogatella fur)
cifera), brown planthopper (Ni1apa-r)
vata lugens), brown-bottomed planthopper (La
oderphax 5tria-tellus), Hon-heli stink bug (T(, 1ptortus clava)
tus ), southern stink bug (Nezara vi
ridula), Nasigunbai (5tephanit)
is nashi ), whitefly (Tria
leurodes vaporariorum),
Cotton aphid (Aphis gossypii),
Green peach aphid (Myzus Persicae),
Unaspis yanone
nsis), from the Lepidoptera, for example, Phyllonoryct
er ringoniella), diamondback moth (plu
ttela xylostella), cotton moth (P
romalactisinonisema), Adoxophyes orara, Leguminivora glyci
nivorella), Cnapha
locrocis medinalis), Chilo 5uppressalis, Qstrinia furnacalis
), armyworm (Mamestra brassicae)
), Pseudaletia 5ep
arata), Spodoptera japonica (8podopte)
ra Jitura), Inet beetle (Parnar)
aguttata), cabbage butterfly (Pieris)
rapae crucivora), Coleoptera [Co1
eoptera] to, for example, Doganepuipui (A
nomala cnprea), Pop.
illiajaponica), rice weevil (Ec
hinocnemus squameus, rice weevil (Li5sorhoptrus oryzoph)
Hus), Oulema or″
'yzae), Hime r7+z cutlet beetle (An
threnus verbasci), Kocnust (
Tenebrioides mauritanicus
), weevil (5ito-philus z
eamais), Heno
sepilachna vigintroctopun
ctata), adzuki bean weevil (Ca1losobr
uchus chinensis), Monochamus alternat
us), Au1acophora fe
moralis) Hymenoptera
), for example, Kabrabavachi (Athalia r
osae japonensis ), Arge 51mlis ), Diptera [ Pipt
era], for example, Culex aegypti (Cu1e
x pipiens catigans), Aedes aegyoti, Asphondylia sp., Hylemya pla-tura, Musca domestica vici
na ), Dacus cucurbi
tae), Agremyza o.
ryzae), Cryptera [Aphani ptera]
] as the human flea (Pulex 1rritans)
, Xenopsylla ch.
eopis), dog flea (Ctenocephali)
-des canis), Thysanoptera
tera ] as tea thrips (5 cir
tothrips dorsalis), Thrips tabaci (Thrips tabaci), Ba1iothrips biformis
), as part of the order Anoplura, for example, the body lice (pediculus humanus).
corporis), pubic louse (Phthirus
pubis), Psocoptera
a), for example, Trogi
u+n pulsatorium), Liposcelis bostrychophi
lus), Qryllotalpa africana as Orthoptera [:0rthopte-ra]
), Locusta migrat
oria), Kobanei Locust (OX'/a japon)
ica), German cockroach (Blattellage)
rmanica), black cockroach (Periplan
eta fuliginosa), Acariformes [Acar
ina], for example, Nami...Dani (Tetra
nychus urticae), citrus urticae (
Panonychuscitri), Tetranychus telarius, Tetranychus Kanzaw
ai), Rhizoglyphus ec
hinopus).

When the compound of the present invention is actually used, it can be used alone as it is depending on the purpose of use, but in order to enhance or stabilize the effect, it may be mixed with a pesticide adjuvant to form a formulation and then used directly, but as necessary. It is generally applied after dilution. The compounds of the present invention can be formulated into powders, granules, fine granules, water-containing agents, flowable agents, emulsions, and microcapsules by methods commonly used in the agricultural chemical manufacturing field without requiring any special conditions. , oil,
Aerosols, heated fumigants (mosquito coils, electric mosquito repellents, etc.),
It can be used in any formulation form, including fogging agents, non-thermal fumigants, and poison baits.

The agrochemical auxiliaries mentioned herein include carriers (diluents) and other auxiliaries such as spreading agents, emulsifiers, wetting agents, dispersants, fixing agents, and disintegrants. Examples of liquid carriers include aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol, and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, methylnaphthalene, cyclohexane, Examples include animal and vegetable oils, fatty acids, fatty acid esters, and petroleum fractions such as kerosene and light oil.

Solid carriers include clay, kaolin, talc, diatomaceous earth,
Examples include silica, calcium carbonate, montmorillonite, bentonite, -feldspar, quartz, alumina, and sawdust.

In addition, surfactants are usually used as emulsifiers or dispersants, such as anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine, and cationic surfactants. agent,
Examples include nonionic surfactants and amphoteric surfactants.

Spreading agents include polyoxyethylene nonylphenyl ether and polyoxyethylene lauryl ether, wetting agents include polyoxyethylene nonylphenyl ether dialkyl sulfosuccinate, and fixing agents include carboxymethyl cellulose. ,
Examples include polyvinyl alcohol, and disintegrants include sodium pyrogenin sulfonate and sodium lauryl sulfate.

Furthermore, by using two or more of these compounds of the present invention in combination, it is possible to express superior insecticidal and acaricidal activity, and it is also possible to express superior insecticidal and acaricidal properties, and to use other physiologically active substances such as allethrin,
Phthalthrin, permethrin, techamethrin, fenvalerate, α-cyano-3-phenoxybenzyl 2.2
- Pyrethroid and various isomers such as dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carboxylate, pyrethrum extract, organophosphorus insecticides such as DDVP, fenitrothion, diazinon, temephos, NAC, MTMC, BPMC, Bilimar etc. (1) Carbamate insecticides, other insecticides, acaricides or fungicides, nematicides, herbicides, plant growth regulators, fertilizers,
By mixing it with BT agents, insect hormone agents, and other agricultural chemicals, it is possible to create a multipurpose composition with even greater efficacy, and a synergistic effect can also be expected.

Furthermore, the efficacy can be increased several times by adding known synergists for pyrethroids, such as piperonyl butoxide, sulfoxide, safroxane, etc.

The compounds of the present invention have high stability against light, heat, oxidation, etc., but if necessary, antioxidants or ultraviolet absorbers, such as phenols such as BHT and BHA, arylamines such as α-naphthylamine, and alkaline Or by adding benzophenone compounds 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. In some cases, it may be only the active ingredient compound, but it is usually 0.2 to 95% (by weight), preferably 0.5 to 80%. % (weight) range.

The amount of the composition of the present invention to be used depends on the dosage form, method of application, timing,
Although it varies depending on other conditions, good gardening agents, forest pest control agents, and pasture pest control agents usually have an active ingredient amount of 10 to 300 per 10 are. , preferably 15 to 200 tons, and the sanitary pest control agent is usually 1W? 2 in terms of active ingredient amount per unit
~200 mg, preferably 5-1100 In is used. For example, powders have an active ingredient of 15~10 are.
1201, the active ingredient for granules is 30-240F, and the active ingredient for emulsions and water preparations is 40-250? is within the range of However, in special cases it is possible, and sometimes even necessary, to exceed or fall below these ranges.

Next, formulation examples of the present invention will be explained in more detail in the following examples, but the types and mixing ratios of additives are not limited to these and can be used in a wide range.

Note that "parts" means "parts by weight."

Formulation example 1. Emulsion Compound of the present invention (each compound of Examples 1 to 8, the same applies hereinafter)
65 parts of a xylene-methylnaphthalene mixture was added to 20 parts and dissolved, and then 15 parts of a mixture (8:2) of alkylphenol oxidized ethylene condensate and calcium alkylbenzenesulfonate was mixed thereto to form an emulsion. The main rule is to dilute it with water and use it as a spray solution.

Formulation example 2. Irrigation agent 10 parts of the compound of the present invention, 745 parts of kaori, 30 parts of clay,
Mix 7.5 parts of diatomaceous earth, and then add a mixture of sodium laurate and sodium dinaphthyl methanesulfonate (1:1).
) and 7.5 parts were mixed and pulverized to obtain a powder. The main rule is to dilute it with water and use it as a spray solution.

Formulation example 3. Powder One part of the compound of the present invention is mixed with a mixture of talc and calcium carbonate (
After adding 97 parts of 1:1) and mixing and grinding to sufficiently evenly disperse and blend, 2 parts of silicic anhydride are further added, and the mixture is mixed and ground to form a powder. The main rule is to scatter and use as is.

Formulation Example 49 Granules 2 parts of the compound of the present invention are mixed with 48 parts of bentonite fine powder, 48 parts of talc, and 2 parts of sodium ligninsulfonate, and then water is added and kneaded until uniform. Next, the mixture is granulated through an injection molding machine, and passed through a sieve and dryer to obtain granules with a particle size of 0.6 to 1+m. The main rule is to use it by directly scattering it on the paddy field and soil surface.

Formulation Example 5, Oil: 0.1 part of the compound of the present invention and 0.5 parts of piperonylbutyroside
Add 1 part to 100 parts and dissolve in white kerosene to make an oil solution. The basic rules will be used as is.

Formulation example 6. Aerosol Mix and dissolve 0.4 parts of the compound of the present invention, 20 parts of piveronyl butoxide, 6 parts of xylene, and 7.6 parts of deodorized kerosene, fill it into an aerosol container, attach the Tsukuru part, and then the Nogrug part. If 86 parts of Freon is processed into an aerosol, it will become an aerosol.

Formulation example 7. Heated fiber fumigation insecticidal composition When 0.05P of the compound of the present invention is dissolved in an appropriate amount of chloroform and evenly adsorbed onto the surface of asbestos measuring 2.5 crn x 15 cIn and 0.3 m thick, a heated fiber fumigation insecticidal composition on a hot plate is obtained. becomes.

Formulation example 8. Mosquito coil Dissolve 0.51 of the compound of the present invention in 20 ml of methanol, and uniformly stir and mix with 995 parts of incense coil carrier (mixing tab powder: lees powder: wood flour in a ratio of 3=5=1), and then dissolve in methanol. After evaporating, add 150 ml of water, mix well, mold and dry to make mosquito coil.

Next, the effects of the present invention will be specifically explained using test examples.

Comparative compounds (A) and (B) shown below were used as control compounds and were tested in the same manner as the compounds of the present invention.

Test example 1. Effect on resistant leafhopper and susceptible leafhopper A 20% emulsion of the compound of the present invention and a comparative compound was prepared according to Formulation Example 1 and used as a test drug, and B as a control drug.
PMC (2-5ee-butylphenylmethylcarbamate) 50% emulsion, diazinon (diethyl 2-iso-
A 40% emulsion of propyl-4-methyl-6-pyrimidinyl phosphorothionate was used.

Test method: 5 to 6 rice plants at the 3- to 4-leaf stage were immersed for 15 seconds in a treatment solution diluted with water so that the active ingredient of each test chemical was 4001) pm.

After air-drying, place in a glass cylinder with a diameter of 4.5 cr71 and a height of 15 crn, and place 10 female adult insects of susceptible leafhopper (superood) and leafhopper resistant to organic phosphorus and carbamate agents (intercultivation origin and water flow). The head was released, covered with a wire mesh lid, and left in a glass greenhouse. Forty-eight hours after the treatment, the number of live and dead bundles was investigated, and the mortality rate was calculated. The results are shown in Table 1 as the average value of two series.

Table 1 Test Example 2. Effect on brown planthopper A 10% aquarium containing the compound of the present invention and a comparative compound was prepared according to Formulation Example 2 and used as a test drug.

Test method: The test was carried out in the same manner as in Test Example 1, and 10 adult female brown planthoppers were released. After 48 hours of treatment, the number of live and dead insects was investigated, and the mortality rate was calculated. The results are shown in Table 2 as the average value of two series.

This brown planthopper is organic phosphorus. Addition of resistance to agents and carbamates The Seda amount was used.

Table 2 Test Example 3. Effect on Culex Culex larvae 0.1% acetone solutions of the compounds of the present invention and comparative compounds were prepared and used as test agents.

Test method: 195ml of well water in a plastic container with a diameter of 9.
20 3rd to 4th instar larvae of Culex pipiens (from Ageo) were released, and 5 ml of the test agent was applied dropwise with a pipette. The concentration of the chemical solution at this time is 11) pm. After 24 hours, the number of live and dead insects was investigated and the mortality rate was calculated.

The results are shown in Table 3.

Table 3 Test Example 4. Effect on adult two-spotted spider mites A 20% emulsion of the compound of the present invention and a comparative compound was prepared according to Formulation Example 1,
It was used as a test drug.

Test method: The first leaves of green beans grown in a clay pot with a diameter of 9 cm are shaped into a size of approximately 3 crn x 3 cm, and each leaf is carefully inoculated with 15 female adults of an organic phosphorus-sensitive line using a small brush. . Leave it in a greenhouse controlled at 25°C for one day. One day after inoculation of adult insects, dead and unhealthy insects were removed, and 10% of each test drug was added to the treatment solution diluted with water so that the active ingredient was 400 ppm.
Immersed for seconds.

After the treatment, it was left still in the above greenhouse. 48 Life and death of spider mites under a stereomicroscope after hours The number of insects was investigated and the mortality rate was calculated.

The results are shown in Table 4.

Table 4 Patent applicant: Nippon Kayaku Co., Ltd.

Claims (1)

[Claims] (In the formula, R1 represents a hydrogen atom, a chlorine atom, or a methyl group, and R2 is) - A lower alkyl group substituted with a rogene atom, - A lower alkenyl group substituted with a gen atom, or -・Represents a saletacyclopropylmethyl group substituted with a rogene atom, and X represents 01 or 2. ) Methanesulfonate derivatives represented by R, 2S (0)
represents a lower alkenyl group substituted with a halogen atom or a cyclopropylmethyl group substituted with a halogen atom,
X represents 0.1 or 2. ) An insecticidal composition containing a methanesulfonate derivative represented by the following as an active ingredient.