JPS61118367A - Alkanesulfonate derivative, and insecticidal, miticidal and nematocidal composition containing said derivative as active component - Google Patents

Abstract

NEW MATERIAL:The alkanesulfonate derivative of formula I (R<1> is 1-12C alkyl; R<2> if R<1> or halogen-substituted 1-4C alkyl; x is 0-2). EXAMPLE:6-N-propylthio-20pyridylmethanesulfonate. USE:Insecticidal, miticidal and nematocidal agent effective to the larva of green rice leafhopper and common gnat and imago of two-spotted spider mite, etc. Vermin on the leaf can be controlled by applying the agent to the base of the plant as well as by contacting with the vermin. It can be used also as a systemic insecticide having extremely low phytotoxicity to the host crop. It can be applied in paddy field, plowed land, orchard, forest, etc. PREPARATION:The compound of formula I can be prepared by reacting the compound of formula II (Y is H, alkali metal or alkaline earth metal) with sulfonyl chloride of formula III or sulfonic anhydride of an acid acceptor, at -10-+100 deg.C, preferably 0-40 deg.C for 0.5-10 hr.

Description

[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to a novel alkanesulfonate compound and proboscis. It can be used as a drug.

[Conventional technology]

It is known that certain alkanesulfonate derivatives are useful as active ingredients in insecticides and nematicides.

For example, 3-n-phylthiophenyl methanesulfonate is disclosed in Japanese Patent Publication No. 3898/1973, and 3-ethylsulfonylphenyl methanesulfonate is disclosed in Japanese Patent Publication No. 1977-3898.
In Publication No. 98025.

Dilmethane sulfonate has been reported to have nematicidal activity.

[Problem that the invention seeks to solve]

Conventional alkanesulfonate derivatives do not have sufficient insecticidal effects against insects that have acquired resistance to insecticides such as organophosphate agents and covermate agents, as well as highly susceptible insects, and cannot be used to control the above insects at low doses. A compound that can do this has been desired.

[Means for solving problems]

As shown in (1) below, the present inventor has introduced an alkylthio, alkylsulfinyl, or alkylsulfonyl group into the 6-position of the pyridine ring and an alkanesulfonylox 7 group into the 2-position, thereby killing insecticidal, acaricidal, or sterilizing substances. It was discovered that a compound with high nematode activity can be obtained.

(In the formula, Bt represents an alkyl group of 01 to C1□, and R
2 represents a C1-C1□ alkyl group or an 01-C4 alkyl group substituted with a halogeno atom, and X is 0.1 or 2; ) The compound of formula (1) of the present invention is a compound of formula (wherein R1 and X have the same meanings as above, and Y represents a hydrogen atom, an alkali or alkaline earth metal atom, etc.); Sulfonyl chloride represented by the formula % formula % () (wherein R2 has the same meaning as above) or the formula (R”802)2
0 (rV) (wherein R2 has the same meaning as above) in a solvent at -10° in the presence of an acid binder if necessary.
C~100℃, preferably 0.5~1 at 00C~40℃
It can be produced by reacting for 0 hours.

Examples of solvents include water, aromatic hydrocarbons such as benzene, toluene, and xylene, aliphatic hydrocarbons such as hexane, heptane, and petroleum benzine, halogenated hydrocarbons such as chloroform and dichloromethane, and aprotons such as dimethylformamide and dimethyl sulfoxide. Donating polar solvents, lower alcohols such as methanol and ethanol,
Diinoprobyl ether, diethyl ether, 1.2-
Ethers such as dimethoxyethane, tetrahydrofuran and dioxane, nitriles such as acetonitrile and propionitrile, and ketones such as acetone, diisopropyl ketone' and methyl ethyl ketone 7 can be used. As acid binders, bases include alkali metal hydroxides (NaOH, KOH, etc.), alkaline earth metal hydroxides (Ca(OH)2, Mg(OH)2, etc.)
Alkali metal hydride, alkali metal alcolade (sodium alcolade, etc.) alkali metal oxide (Na2
O, R20, etc.) Alkali metal carbonates (soda ash, etc.)
, aliphatic and aromatic tertiary amines such as sodium amide, triethylamine, dialkylaniline, and pyridine.

Silver oxide can also be used as the acid binder.

Furthermore, the desired alkanesulfonate derivative can also be obtained in good yield by using a phase transfer catalyst such as tetra-n-butylammonium gromide or triethylbenzylammonium chloride as a catalyst.

Moreover, the compound of formula (1) where x=1 or 2 can be obtained by obtaining the compound of x=Q by the above-mentioned method and then treating the compound with an oxidizing agent such as hydrogen peroxide.

That is, when reacted for 3 to 7 hours at 0°C to 50°C in acetic acid containing 1.0 to 2.0 times the mole of hydrogen peroxide, r = 1.
can be obtained, whereas when reacted in acetic acid containing 2.0 to 3.0 times molar hydrogen peroxide at 0°C to 100°C, preferably at 60°C to 100°C for 2 to 5 hours, x =
Compound 2 can be obtained in good yield.

In addition to hydrogen peroxide, examples of oxidizing agents for converting the compound of x = Q to x = 1 in formula (I) include organic peroxides, logogenides, periodates, nitrogen oxides, ozone, and metal oxides. It can also be obtained by air oxidation or anodic oxidation.

In (1), x = Q or the compound where x = 1 is
In addition to hydrogen peroxide, as an oxidizing agent to convert to the compound of = 2,
For example, peracids, hydroperoxides.

・・・Rogen, ・Rogenating agent, ozone, oxygen and transition metal catalyst, potassium peroxysulfate, potassium permanganate, dinitrogen tetroxide, sodium metaperiodate, osmium oxide (monovalent), ruthenium oxide (monovalent) ), sodium dichromate, nitric acid, etc. Oxidation using an electrode is also possible.

The starting material viridinol derivatives of the formula (former) are prepared by known methods (e.g. U.S. Pat. No. 3,335,146), namely by reacting 6-logenoviridinol with an alkyl mercaptan.

In the compound of formula (I) of the present invention, C2 of R1 and R2
Examples of the alkyl group of ~CI□ include methyl, ethyl, n-7", a, n-
Butyl, 5ec-butyl, 1so-butyl, n-amino,
・L, 1so-amyl, 5ee-amyl, rhohexyl, n-octyl, n-lauryl, etc.
Examples of the C1-C, alkyl group substituted with a logen atom include chloromethyl, trifluoromethyl or 2-chloroethyl group, 3-bromopropyl group, and 4-raabutyl group.

When the compound of the present invention is actually used, it is common to mix the agents to be used and prepare a preparation, which is then used directly or diluted as necessary. No special conditions are required to formulate the compound of the present invention, and powders,
Granules, fine granules, irrigation agents, flowable agents, emulsions, microcapsules, oil agents, aerosols, heating fumigants (mosquito coils, electric mosquito repellents, etc.), fumigants such as Phonoking, non-heating fumigants, poison baits, etc. It can be used in any formulation form.

The agrochemical auxiliaries mentioned herein include carriers (diluents) and other auxiliaries such as spreading agents, emulsifiers, wetting agents, dispersants, fixing agents, and disintegrants. As a liquid carrier.

Aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetono, amides such as dimethylformamide,
Sulfoxides such as dimethyl sulfoxide, methylnaphthalene, cyclohexane, animal and vegetable oils, fatty acids.

Examples include fatty acid esters, and petroleum fractions such as kerosene and light oil.

Solid carriers include clay, kaolin, and talc.

Diatomaceous earth, 7 Lika, calcium carbonate, montmorillonite,
Examples include indianite, 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, polyoxine ethylene alkylphenyl ether, lauryl betaine, and cationic surfactants. , nonionic surfactants, and amphoteric surfactants.

Spreading agents include polyoxyethylene nonylphenyl ether and holoxyethylene lauryl ether, wetting agents include hapolyoxyethylene nonylphenyl ether dialkyl sulfosuccinate, and fixing agents include carboxymethyl cellulose, Polyvinyl alcohol fx is used as a disintegrant, and disintegrants include sodium chloride 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-7ano-3-phenoxybenzyl 2,2
- Pyrethroids and various isomers such as dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carboxylate, organophosphorus insecticides such as Chrysanthemum extract, DDVP, phenitrothion, diazino/, and temephos,
Carbamate insecticides such as NAC, MTMC, BPMC, Bilimar, other insecticides, acaricides or fungicides, nematicides, herbicides, plant growth regulators, fertilizers, BT agents, insect hormone agents, and other agricultural chemicals By mixing with other substances, a multipurpose composition with even greater efficacy can be created, and synergistic effects can also be expected.

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

The compound of the present invention has high stability against light, heat, oxidation, etc., but if necessary, antioxidants or ultraviolet absorbers, such as phenols such as BHT and BHA, α-su7
By appropriately adding arylamines such as thylamine or 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, only the active ingredient compound may be used, but it is usually 0.2 to 95 cm (weight), preferably 0.5 to 80 cm. (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, agricultural and horticultural agents, forest pest control agents, and pasture pest control agents are usually used in an amount of 10 to 300 g of active ingredient per 10 ares, preferably 15 to 200 g, and sanitary pest control agents are used. Usually 2 to 2 active ingredients per serving
001n9, preferably 5-1oOrn9 is used. For example, for powders, the active ingredient is 15 to 1 per 10 ares.
20g of the active ingredient, 30 to 240g of the active ingredient for granules, and 40 to 250g of the active ingredient for emulsions and wettable powders. However, in special cases it is possible, and sometimes even necessary, to exceed or fall below these ranges.

Specific pest insects to which the insecticidal, acaricidal, and nematicidal compositions of the present invention can be applied are listed below.

From the order Hem1ptera, for example, the leafhopper (Nephotettix cinctice)
ps), white-legged planthopper (Sogatella fu)
rcifera), brown planthopper (Ni1ap)
arvata lugens), brown-bottomed planthopper (L.
ao-delphax 5triatel Ius)
, Rip-tortus cl.
avatus), Minamia Okamemun (Ne-zar)
a viridula), Nasigunbai (5teph
anitisnashi), Onji y-t nashi (
Trialeurodesvaporariorum
), cotton aphid (Aphis goss-ypii
), peach aphid (Myzus persica
e), Unaspis yano
nensis), Lepidoptera (Lepidoptera
) to ft:, Toeha jr 7% / Hosoga (
Phyllonorycter ringoneell
a), diamondback moth (Plutella xyloste)
lla), cotton moth (Promalact isi)
nonisema) , :I Kakumon Hamaki (Ado
xophyesorana), Mameshinkuiga (Le
guminivora glyci-nivorell
a) , :I Cnaphalocroc
is medi-nalis), Chil
o 5uppressal is), American foxtail moth (
Ostrinia furnacalis), armyworm (Mamestra brassicae), fall armyworm (Pseudale-tia 5eparata)
), Hasmoa Spodoptera (5pOdOptera1itu
ra), rice throat beetle (Parnara gutt)
ata), Mont 70 butterfly (P 1eris rap)
ae crucivora), Coleoptera (Coleoptera)
ptera) to Doganepuipui (Ano).
mala cuprea),? Mekogane (Popi)
llia japo-nica), rice oum/(Ec
hinocnemus soqameus), Li5sorhoptrus oryzop
hilus), rice beetle (Oulema o.
ryzae), Himemarukatsuopsimun (Anth
renus verbasci), Kocnust (Te
nebroides mauritanicus),
Weevil (S 1tophi lus zeama)
is ), Nijuyaho7te/tou (Henosepi
lachna vigintioctopunctat
a), Adzuki bean weevil (Ca1losobruchu)
s chinensis ),? Monochamus alternatus,
Au1acophora femora
is) As a member of the order Hymenoptera, for example, Athal ia ro
sae japonensis ), Arge japonensis ( Arge 51m1 is ), Diptera (
For example, Diptera:]
Cu1ex pipiens fatigans),
Aedes aegypti, Asphondyl ia sp,
), Hylemya platura
), house fly (Musca domestica vi
cina), Urimino (engineering), Dacus cucu
rbitae), rice leaflet fly (Agromyz
a oryzae), Hymenoptera (Aphaniptera)
a) as human flea (Pulex 1rritans)
), Xenopsyl la
cheopis), dog flea (Cteno-+-ce
phal 1des canis), Hymenoptera (Thy
sanoptera) as tea thrips (Cirtothrips dor-salis),
Thrips tabaci, rice thrips? (Ba1iothrips bifor
mis ), '/Anoplura, for example, the body lice (Pediculus hum).
anus corporis), pubic louse (Pth-
irus pubis), Psoc
For example, cochatate (Tro optera)
gium pulsato-rium), Liposcel is bostrycb-weak part, Orthoptera
ta migratoria), Kobanei Locust (0x
ya -j-al-←1S-), German cockroach (Blattel la ge
rmanica), Kurogokifisu (Periplan)
eta fuliginosa), Acariformes (Acan
For example, Tetrany mites
chus urticae), orange spider mite (Pan
Ony-Needani (Rhizoglyphus echi)
nopus).

Among nematodes, TYLENCHIDA
For example, soybean cyst nematode (Hetero-
(Meloidogyne incognita)
, Pratylenchu
s neglectus), Aphelenchoides besseyi
, eight phelenchoides
ritzemabosi), Matsunozaisencheu (
Bursa phelenchus l 1gn1co
lus).

The compound of the present invention can not only control pests by contact, but also control pests on the leaves by applying the chemical to the base of the plant. It is an excellent insecticide, acaricide, and nematocide with almost no chemical damage to the human body.

=Example] The present invention will be explained below with reference to Examples.

Synthesis Example Synthesis Example 1. 6-N-propylthio-'l-
pyridyl methane sulfonate
(NcLl)6-n-propylthis-
3.4 g of 2-pyridinol and 22 g of anhydrous sodium carbonate were added to 25 ml of N,N-dimethylif
Suspend in ormamide and stir. Met at 100C
hanesulfonyl chloride 2.4
After dropping, remove the bath and leave to warm to room temperature. The mixture was then heated to 50'C and stirring continued for 2.5 hours.

The reaction solution was poured into 200 ml of cold water and extracted twice with ether. The ether layer is washed with 50% sodium chloride solution, water, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent was purified by silica gel column chromatography (toluene
? 7) to purify the desired 6-n-propy
lthio-2-pyridylmethanes
3.9 g (yield 78.8%) of ulfonate was obtained as a pale yellow oil.

nD” 1.5465°PMR (CCV, ), 6: 100 (t, 3
H), 1.78 (q, 2H), 3.07 (t, 2H),
3.34 (s, 3H), 6.73 (d, IH), 7
．． 09 (d, LH), 7.58 (d, LH) ppm
.

Synthesis example 2. 6-1so-propylsuefon
yl-2-pyridylmethanesulf
Synthesis of onate (Nn 22 ).

6-iso-propylsulfonyl-2
-pyridinol 2.2 g and methane
esulfonyl chloride 1.48 g
is dissolved in 3Qml of methylene chloride, and 1.65g of triethylamine is added dropwise at below 10°C. Then at room temperature 2
The reaction is completed after stirring for 2 hours at 50-60°C. Pour the contents into 100 ml of cold water and separate the methylene chloride layer. The aqueous layer is further extracted with methylene chloride, and the organic layers are combined. This was washed with water, the solvent was distilled off, and the resulting residue was purified using silica gel column chromatography (acetic acid ethyl n-hexane) to obtain the desired 6-i5o-propyls.
ulfony, l-2-pycidyl meth
nesulfonate2.4g (yield 76.0%
) was obtained as colorless crystals.

m, p, 70.5-71.5°C PMR (CCI,), 6: 1.40 (d,
3H), 3.69 (s, 3H), 3.51-3.88
(m, IH), 7.57-7.74 (m, IH), 8
．． 30-8.57 (m, 2H) Synthesis Example 3. 6-I
so -butylhio -2-pyridyl t
riflusromethane 5ulfonate
Synthesis of (N11139): 5-iso-butylthis-2-pyr
A mixture of 6.5 g of idiool and 50 ml of pyridine is stirred and cooled to below 10°C. here trifluorome'□ne sul fonic
anhydr'? Add 1 lreI Q g dropwise.
After that, gradually return to room temperature, and leave at room temperature for 2 hours at 50~60℃.
The reaction is complete after stirring for 1 hour at 0°C.

The contents are poured into 200 ml of cold water and extracted twice with benzene. When the residue obtained by distilling off benzene is purified by chromatography (toluene-〇-hexane), the desired 5
- i5o -butyl de hio -2-pyidy
l trifluoromethane 5ulfon
ate 9.3g (yield 84.3%) was obtained as a colorless oil.

nD” 1.4827 PMR (CDCI,) δ: 1.04 (d, 6
H), 1.98 (m, IH), 3.04 (d, 2H)
, 6.76 (d, IH), 7.20 (d, IH),
7.59 (t, IH) Synthesis Example 4. 6-N-Pr
opylsulfinyl-2-pyridyl m
Synthesis of ethanesulfonate (N112.)゛6-n-propulthis-2-py
ridyl methanesul -fonate
(NcLl) 2.83 g was dissolved in 20 ml of acetic acid, and 1.7 ml of 35% hydrogen peroxide solution was added dropwise to the solution at room temperature. After stirring for 3.5 hours, 1 ml of 35% hydrogen peroxide solution was further added and the reaction was continued for 3 hours.

The reaction solution was poured into 50 ml of cold water and extracted twice with toluene. The toluene layer was washed with 5% NaOH until neutralized.
Wash further with water. After drying with anhydrous sodium sulfate and distilling off the solvent, the desired 6-n-propylthios
ulfinyl-2-pyridylmethane
e5ulfonate 2.2 g (yield 73.3%
) is obtained as colorless crystals.

m, ri, 51-53°C PMR (CDCI3) σ: 1.06 (t, 3
Hl 1.7!5 (m, 2H), 2.94 (m,
2H), 3.47 (s, 3H), 7.19 (t
, zH), 7.88~8.15 (m, 2
H) ppm synthesis example 5. 6-N-propylsu
lforyl-2-pyridyl methane
Synthesis of sulfonate (Nn3): 6-n
-propylthio -2-pyridyl m
ethanesu[-fonate (tII+11
) Dissolve 2.2 g in 3Qml of acetic acid, and add 35g to this.
% Add 2.6 ml of hydrogen peroxide solution at room temperature. 80-9
The reaction is complete after stirring at 0°C for 4 hours. The reaction solution is poured into water, extracted twice with methylene chloride, and the extract is washed with 5% caustic soda solution until neutral.

Further wash with water and dry with anhydrous sulfuric acid (IJum). When the solvent is completely distilled off, the target 6-0-5propylsulfonyl-2-pyrLe-4
yl methanesulfonatel, 6g
(yield 68.3%) is obtained as a pale brown oil.

nD251.5237 PMR (CDCl3) δ: 1.03 (t,
3H), 1.77 (m, 2H), 3.33 (m,
2H), 3.58 (s, 3H), 7.46 (d,
IH), 8.06-8.34 (m, 2H) pp
Compounds of the present invention were further synthesized by m-synthesis synthesis-1 to 5 methods.

Representative ones are shown in Table 1.

l'ujiang formulation example 1. Emulsion 65 parts of a mixed solution of xylene-methylnaphthalene was added to 20 parts of the compound of the present invention and dissolved, and then in step (a), 15 parts of a mixture (8:2) of alkylphenol oxide ethylene condensate calcium toalkylbenzenesulfonate was mixed therein. Make it into an emulsion. The main rule is to dilute it with water and use it as a spray solution.

Formulation example 2. irrigation agent 35 parts of kaolin to 20 parts of the compound of the present invention.

30 parts of clay and ±7.5 parts of diatoms are mixed, and further 7.5 parts of a mixture of sodium laurate and sodium dinaphthyl methanesulfonate (1:1) is 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 97 parts of a mixture of talc and calcium carbonate (1:1) was added to 1 part of the compound of the present invention Th, mixed and ground to sufficiently evenly disperse and blend, and then 2 parts of silicic anhydride was added, mixed and ground to form a powder. shall be. The main rule is to scatter and use as is.

Formulation Example 4 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 lignin sulfonic acid, 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 wit.

The main rule is to use it by directly scattering it on the paddy field and soil surface.

Formulation example 5. Oil agent: 0.1 part of the compound of the present invention and 0.5 parts of piperonyl butoxide.
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 0.4 parts of the compound of the present invention, 20 parts of piperonyl gtoxide, 6 parts of xylene, and 7.6 parts of deodorized kerosene are mixed and dissolved, filled into an aerosol container, and a pulp section is attached. If the part is processed and exposed to light, it becomes an aerosol.

Formulation example 7. Heating fiber fumigation insecticidal composition: 0.05 g of the compound of the present invention is dissolved in an appropriate amount of chloroform and evenly adsorbed on the surface of asbestos of 2.5 cm x 1.5 m (0.3 m thick), heated on a hot plate. It becomes a fiber fumigation insecticidal composition.

Formulation example 8. Mosquito coil Dissolve 0.5 g of the present compound in 20 ml of methanol, and uniformly stir and mix with 99.5 parts of incense coil carrier (mixing tab powder: lees powder: wood flour at a ratio of 3:5:1). After evaporating the methanol, 150 ml of water was added and the mixture was thoroughly kneaded, molded and dried to produce mosquito coils.

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

Comparative compounds (5), (g), and (q) shown below were used for the test in the same manner as the compounds of the present invention.

5o2C2I(.

Test Example Test Example 1. Effect on resistant black leafhopper and susceptible black leafhopper Regarding the compounds of the present invention and comparative compounds, if the drug substance is a crystal, a 20-chi wettable powder is prepared, and if the drug substance is an oily substance, a 20-chi emulsion is prepared according to Formulation Examples 1 and 2. and as the test drug,
Furthermore, as control drugs, BPMC (2-see-butylphenylmethylcarbamate) 50% emulsion, diazinon (diethyl 2-i3°-propyl-4-methyl-6-
A 40% emulsion of 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 200 ppm.

After air-drying, it was placed in a glass cylinder with a diameter of 4.5 CrrL and a height of 151 cm, and a susceptible leafhopper (from Ageo) and a leafhopper (from the mid-periphery and water flow) resistant to both organic phosphorus and carbamate agents were placed. Ten female adults were released, covered with a wire mesh lid, and left in a glass greenhouse. After 48 hours of treatment, the number of live and dead vehicles was investigated and the mortality rate was calculated. The results are the average values of two series and are shown in Table 2.

Table 2 Test Example 2. Effect on brown planthopper 20% aquariums or 20% emulsions of the compounds of the present invention and comparative compounds were prepared according to Formulation Examples 1 and 2 and used as test drugs.

Test method: Conducted in the same manner as in Test Example 1, 10 female adult brown planthoppers were released, and 48 hours after treatment, the number of live and dead vehicles was investigated, and the mortality rate was calculated. The results are shown in Table 3 as the average value of two series.

Furthermore, this brown planthopper is Passive lines from Kaseda and Lining agent and carbamate agent The amount of water resistant to water flow was used.

Table 3 Test Example 3. Effect on Mo. larvae A 0.1% acetate/solution of the compound of the present invention and a comparative compound was prepared and used as a test drug.

Test method: Well water 19 in a plastic container with a diameter of 9 crIL
9.8 ml of the test agent was added, 20 3rd to 4th instar larvae of Chicae mosquito (from Ageo) were released, and 0.2 ml of the test agent was applied dropwise with a pipette. The concentration of the chemical solution at this time is 1 ppm. After 24 hours, the number of dead and alive cars was investigated and the mortality rate was calculated.

The results are shown in Table 4.

Table 4 Test Example 4. Effect on adult mites 20% hydrated powders or 20% emulsions of the compounds of the present invention and comparative compounds were prepared according to Formulation 1 and 2 and used as test drugs.

Test method: First leaves of green beans planted on a clay pot with a diameter of 9 (m) were shaped into a size of approximately 3crIL x 3cIrL, and 15 female adults of an organic phosphorus-sensitive strain were carefully collected on each leaf using a small brush. Inoculate. Leave in a greenhouse controlled at 25°C for 1 day. 1 day after inoculating adults.

Remove dead and unhealthy insects.

The active ingredient of each test drug is 400 Dilute with water to make ppm It was immersed in the treatment solution for 10 seconds.

After treatment, the traps were left in the greenhouse.

After 48 hours, the cells were examined under a stereomicroscope. Investigate the number of live and dead mites, and The insect rate was calculated.

The results are shown in Table 5.

Test example 5. 201 aquarium or 20ti emulsion of the compound of the present invention and the comparative compound were prepared according to Formulation Examples 1 and 2, used as test drugs, and diazinon (diethyl 2-1So-propyl-4-methyl- 6-pyrimidinyl phosphorothioate) 40% emulsion was used.

Test method: 30 to 50 germinated rice grains were immersed for 15 seconds in a treatment solution diluted with water so that the active ingredient of each test chemical was 200 ppm.

After air-drying, place in a glass cup with a diameter of 9.0 cIrL and a height of 6.03 mm, release 10 3rd instar larvae of Nica meichu, cover with a glass lid, and keep at constant temperature and humidity (temperature 25°C ± 2°C, humidity 80%). ±10%). 24 hours after the execution, the number of dead and alive vehicles was investigated, and the mortality rate was calculated. The results are shown in Table 6 as the average value of two series.

Test example 6. Effect on tomato root-knot nematode disease Tomato root-knot nematode (Meloidogyne inco.
1,400 g of soil contaminated with
40 rng of each of the compounds of the present invention and comparative compounds produced according to Formulation Example 3, and 1 powder of DCIP (bis(2-chloromethylethyl)ether) as a control agent were mixed into the entire layer in a plastic cup.

15 tomato seeds (product: Ponterosa) were sown in each pot.

On the 40th day after the chemical treatment, the test tomatoes were dug up and examined for chemical damage and root gall index. The results are shown in Table 7. The root knot index is calculated as follows.

A: A certain number of bacteria with 31 or more root galls growing on the roots of Nidomad B: #21-30 C: 1 11-20 D 1-10 or more root galls growing on the roots of Nidomad Table 7: Number of bacteria present [Effects of the invention]

Claims (2)

[Claims] (1) Formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) (In the formula, R^1 represents an alkyl group of C_1 to C_1_2, and R_2 is an alkyl group of C_1 to C_1_2 or C_1 substituted with a halogen atom. ~C_4 alkyl group, x represents 0, 1 or 2). (2) Formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) (In the formula, R^1 represents an alkyl group of C_1 to C_1_2, and R^2 is substituted with an alkyl group of C_1 to C_1_2 or a halogen atom. An insecticidal, acaricidal, or nematocidal composition comprising an alkanesulfonate derivative represented by C_1 to C_4 alkyl group, and x represents 0, 1, or 2 as an active ingredient.