JPH066598B2 - Organophosphorus compounds and insecticides, acaricides, nematicides, and soil insecticides containing them - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial field of application) The present invention relates to novel organophosphorus compounds having an effective control action against harmful insects, mites, nematodes, and soil pests. And a pesticide, an acaricide, a nematicide, and a soil pesticide containing the compound as an active ingredient.

(Disclosure of the Invention) The compound of the present invention is a novel organophosphorus compound represented by the following general formula (I).

General formula: (In the formula, R ₁ and R ₂ are alkyl groups, R ₃ is an alkyl group which may be substituted with a hydrogen atom or a halogen atom, and n is an integer of 2 to 6).

In the general formula (I), the alkyl group represented by R ₁ , R ₂ and R ₃ is a methyl group, an ethyl group, a propyl group,
Examples thereof include a butyl group, and examples of the halogen atom contained in R ₃ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

The compound of the present invention can be produced, for example, by the following method. [A] (In the formula, R ₁ , R ₂ , R ₃ and n are as described above,
Hal is a halogen atom) The above reaction [A] is generally carried out in a temperature range of -100 to 50 ° C, preferably -80 ° C to room temperature.

Further, this reaction is carried out in the presence of an acid acceptor, and as the acid acceptor, organic lithium compounds such as n-butyllithium, tert-butyllithium, phenyllithium, sodium hydroxide, potassium hydroxide, hydrogenation Examples thereof include inorganic bases such as sodium and potassium hydride, organic bases such as triethylamine and pyridine. Furthermore, these reactions are preferably carried out in the presence of a solvent, and as the solvent, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene: cyclic or non-cyclic aliphatic hydrocarbons such as hexane and cyclohexane. Kinds: Ethers such as diethyl ether, methyl ethyl ether, dioxane and tetrahydrofuran: Nitriles such as acetonitrile, propionitrile and acrylonitrile: Aprotic polar solvents such as dimethylformamide, dimethyl sulfoxide, sulfolane and hexamethylphosphoric triamide And so on.

The compound of the present invention can also be synthesized, for example, by the following method.

[B]

(In the formula, R ₁ , R ₂ , R ₃ and n are as described above,
X is a halogen atom, Basis or The reaction [B] is usually -10 to 80 ° C, preferably 0.
It is carried out in the temperature range of ℃ to room temperature.

This reaction is carried out in the presence of an acid acceptor, and examples of the acid acceptor include those similar to those used in the above reaction [A]. Further, these reactions are preferably carried out in the presence of a solvent, and examples of the solvent include alcohols such as methanol and ethanol in addition to the same ones used in the above reaction [A].

The starting compound represented by the general formula (II) has the general formula: (Wherein R ₄ is an alkyl group which may be substituted with a halogen atom, and n is as described above), and the compound represented by the general formula (IV) is a compound of the Journal of the
Chemical Society, p. 1177 (1922)
The compound represented by the general formula (V) can be easily synthesized by the method described in (1) above, for example, the following method.

[C]

(In the formula, R ₄ and n are as described above.) Table 1 shows typical examples of the compound represented by the general formula (V) according to the production method [C].

Next, specific synthesis examples of the compound of the present invention will be described.

Synthesis example 1. Synthesis of S-sec-butyl O-ethyl (5-cyclopropanespiro-2,4-dioxo-1-imidazolidinyl) phosphonothiolate (Compound NO.1) 2.5 g of 5-cyclopropanespirohydantoin and 50 ml of tetrahydrofuran After dissolving in a mixed solvent consisting of 5 ml of hexamethylphosphoric triamide, 1.67 g of sodium hydride (60%) was gradually added under water cooling. After the addition was completed, the liquid temperature was gradually returned to room temperature and stirred for 1 hour and a half.

Next, the reaction solution was cooled with ice, and 10 ml of a tetrahydrofuran solution containing 4.7 g of S-sec-butyl O-ethyl and phosphoric acid ester chloride was gradually added dropwise. After the completion of dropping, the reaction was completed by stirring for 2 hours while gradually returning the liquid temperature to room temperature.

After the reaction was completed, the reaction mixture was poured into 200 ml of ice water, and 10
It was neutralized with% hydrochloric acid. Next, 200 ml of ethyl acetate was added for extraction, the organic layer was washed with brine and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, ethyl acetate was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 4.6 g of the desired product having a melting point of 95 to 97 ° C.

Synthesis example 2. Synthesis of S-sec-butyl O-ethyl (5-cyclobutanespiro-2,4-dioxo-1-imidazolidinyl) phosphonothiolate (Compound NO.2).

2-cyclobutane spirohydantoin 2g tetrahydrofuran 50ml, hexamethylphosphoric triamide 5ml
After dissolving in a mixed solvent consisting of and, 1.17 g of sodium hydride (60%) was gradually added under water cooling. After the addition was completed, the liquid temperature was gradually returned to room temperature and stirred for one and a half hours.

Next, the reaction solution was ice-cooled, and 10 ml of a tetrahydrofuran solution containing 3.4 g of S-sec-butyl O-ethyl phosphate ester chloride was gradually added dropwise. After completion of the dropping, the reaction was completed by stirring for 2 hours while gradually returning the liquid temperature to room temperature.

After the reaction was completed, the reaction mixture was poured into 200 ml of ice water, and 10
The aqueous solution was neutralized with% hydrochloric acid. Next, 200 ml of ethyl acetate was added and extraction was performed. The organic layer was washed with brine and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, ethyl acetate was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give a melting point of 1
2.2 g of the desired product having a temperature of 10 to 112 ° C. was obtained.

Synthesis example 3. S-sec-butyl O-ethyl (5-cyclobutane spiro-3-methyl-2,4-dioxo-1-
Imidazolidinyl) phosphonothiolate (Compound NO.
Synthesis of 3) [I] 5-Cyclobutane spirohydantoin 1.77 g
Was dissolved in 30 ml of methanol, and 1.05 g of sodium methoxide was gradually added at room temperature. Next, 6 ml of methyl iodide was added, and the mixture was reacted at 50 ° C. for 6 hours.

After the reaction was completed, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: ethyl acetate: n-
Purification with hexane = 2: 1) gave 1.36 g of 5-cyclobutanespiro-3-methyl-2,4-dioxo-imidazolidine having a melting point of 135-141 ° C.

[II] 1.36 g of 5-cyclobutanespiro-3-methyl-2,4-dioxo-imidazolidine obtained in the above step [I] was dissolved in 50 ml of tetrahydrofuran and then hydrogenated at 60% under ice cooling. 390 mg of sodium were added slowly.

After the addition was completed, the liquid temperature was gradually returned to room temperature and stirred for 1 hour. The solution is then ice-cooled again and S-sec-butyl O
10 ml of a tetrahydrofuran solution containing 2.1 g of ethyl chlorophosphorothiolate was gradually added dropwise. After completion of dropping, the solution was stirred for 2 hours while gradually returning the temperature to room temperature.

After completion of the reaction, the reaction solution was poured into ice water and ethyl acetate was added for extraction. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate: n-hexane = 1: 3) to obtain a refractive index n _D ^26.4 1.5084. 2.1 g of the product was obtained.

Synthesis example 4. S-sec-butyl O-ethyl (5-cyclopropanespiro-3-methyl-2,4-dioxo-1-
Imidazolidinyl) phosphonothiolate (Compound NO.
Synthesis of 4).

After 820 mg of S-sec-butyl O-ethyl (5-cyclopropanespiro-2,4-dioxo-1-imidazolidinyl) phosphonothiolate was dissolved in 30 ml of tetrahydrofuran, 120 mg of sodium hydride (60%) was added under ice cooling. Gradually added. After completing the addition, gradually return the liquid temperature to room temperature, and
Stir for hours. Next, the reaction solution was ice-cooled, and 0.4 ml of trifluoromethanesulfonic acid methyl ester was gradually added dropwise. After completion of the dropping, the reaction was completed by stirring for 2 hours while gradually returning the liquid temperature to room temperature. After the reaction is completed, the reaction mixture is
The mixture was poured into 100 ml of ice water and ethyl acetate was added for extraction.
After extraction, the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel chromatography (eluent ethyl acetate: n-hexane = 1: 2) to obtain a refractive index n _D ^28.6 1. 640 mg of the target product of 5058 was obtained.

Table 2 lists representative specific compounds included in the present invention.

The compound of the present invention exhibits excellent activity as an active ingredient of pest control agents such as insecticides, acaricides, nematicides and soil pesticides.

For example, spider mites, spider mites, mandarin mites,
Plant parasitic mites such as mite, diamondback moth, weevil, Lotus japonicum, codling moth, ball worm, tobacco bud worm, gypsy moth, Colorado potato beetle, syrup beetle, ballweville, aphids, planthoppers,
Hygiene such as agricultural pests such as leafhoppers, scale insects, stink bugs, whitefly, thrips, grasshoppers, grass flies, scarab beetles, Tamanayaga, Kaburagaga, ants, etc., house dust mites, cockroaches, house flies Storage insects such as pests, Bakuga, Azuki bean weevils, Astragalus vulgaris, Tenebrionidae, etc., clothing such as squid, Pleurotus corridor, termites, house pests, fleas parasitic on other livestock, lice, It is also effective against flies and more, and against plant parasitic nematodes such as root-knot nematodes, cyst nematodes, negusare nematodes, rice pine nematodes, strawberry nematodes, and pine wood nematodes. Is also effective. It is also effective against soil pests. Examples of soil pests referred to here include gastropods such as slugs and snails, and isopods such as pill bugs and wallworms. Further, it is also effective against pests such as dicofol and organophosphorus-resistant plant parasitic mites, organophosphorus-resistant aphids, houseflies and the like. Furthermore, since the compound of the present invention has an excellent osmotic migration property, soil harmful insects, mites, nematodes, gastropods, by treating the compound of the present invention in soil,
It is possible to control the pests on the foliage at the same time as controlling the isopods.

When the compound of the present invention is used as an active ingredient of insecticidal, acaricidal, nematicidal, and soil pesticidal compositions, emulsions, powders, granules and hydrates together with pesticide adjuvants as in the case of conventional pesticide formulations. It can be formulated into various forms such as an agent, a liquid agent, an aerosol agent and a paste agent. The compounding ratio of these is usually 0.5 to 90 parts by weight of the active ingredient and 10 to 9 pesticide adjuvants.
It is 9.5 parts by weight. In the actual use of these preparations, they can be used as they are or diluted with a diluent such as water to a predetermined concentration and used.

Examples of the agrochemical adjuvant include a carrier, an emulsifier, a suspending agent, a dispersing agent, a spreading agent, a penetrating agent, a wetting agent, a thickener, a stabilizer, and the like, which may be appropriately added if necessary. The carrier is divided into a solid carrier and a liquid carrier, and the solid carrier includes starch, activated carbon, soybean flour, wheat flour, wood flour, fish meal,
Animal and plant powders such as milk powder, talc, kaolin, bentonite, calcium carbonate, zeolite, diatomaceous earth, white carbon, clay, alumina, mineral powders such as sulfur powder, and the like, and the liquid carrier includes water, methyl alcohol, ethylene. Alcohols such as glycols, ketones such as acetone and methyl ethyl ketone, ethers such as dioxane and tetrahydrofuran, kerosene,
Kerosene and other aliphatic hydrocarbons, xylene, trimethylbenzene, tetramethylbenzene, cyclohexane, solvent naphtha and other aromatic hydrocarbons, chloroform,
Halogenated hydrocarbons such as chlorobenzene, acid amides such as dimethylformamide, ethyl acetate,
Examples thereof include esters such as glycerin esters of fatty acids, nitriles such as acetonitrile, and sulfur-containing compounds such as dimethyl sulfoxide.

In addition, if necessary, other pesticides, such as insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, herbicides, plant growth regulators, etc., can be mixed and used in combination,
In this case, a more excellent effect may be exhibited.

For example, as an insecticide, acaricide, or nematicide,
O- (4-bromo-2-chlorophenyl) O-ethyl
S-propyl phosphorothioate, 2,2-dichlorovinyl dimethyl phosphate, ethyl 3-methyl-
4- (methylthio) phenylisopropyl phosphoramidate, O, O-dimethyl O-4-nitro-m-tolyl phosphorothioate, O-ethyl O-4-nitrophenyl phenylphosphonothioate, O, O-diethyl O-2 -Isopropyl-6-methylpyrimidine-
4-ylphosphorothioate, O, O-dimethyl O-
Organic such as (3,5,6-trichloro-2-pyridyl) phosphorothioate, O, S-dimethyl acetylphosphoramidothioate, O- (2,4-dichlorophenyl) O-ethyl S-propyl phosphorodithioate Phosphate ester compounds; 1-naphthyl methyl carbamate, 2-isopropoxyphenyl methyl carbamate, 2-methyl-2- (methylthio) propionaldehyde O-methylcarbamoyl oxime, 2,
3-Dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamate, dimethyl N, N '-[thiobis [(methylimino) carbonyloxy]] bisethaneimidothioate, S-methyl-N- (methylcarbamoyloxy) Thioacetimidate, N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide, 2- (ethylthiomethyl) phenyl methylcarbamate, 2-dimethylamino-5,
Carbamate compounds such as 6-dimethylpyridin-4-yl dimethylcarbamate and S, S'-2-dimethylaminotrimethylenebis (thiocarbamate);
2,2,2-trichloro-1,1 bis (4-chlorophenyl) ethanol, 4-chlorophenyl 2,4,5-
Organochlorine compounds such as trichlorophenyl sulfone; Organometallic compounds such as tricyclohexyltin hydroxide; (RS) -α-cyano-3-phenoxybenzyl (RS) -2- (4-chlorophenyl) 3
-Methyl butyrate, 3-phenoxybenzyl (1R
S) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, (RS) -α-cyano-3-phenoxybenzyl
(1RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, (S) -α-cyano-3-phenoxybenzyl (1R) -cis-3- ( 2,2-dibromovinyl)-
2,2-dimethylcyclopropanecarboxylate,
(RS) -α-cyano-3-phenoxybenzyl (1
RS) -cis, trans-3- (2-chloro-3,3,3
3-trifluoropropenyl) -2,2-dimethylcyclopropanecarboxylate, 4-methyl-2,3
5,6-Tetrafluorobenzyl-3- (2-chloro-
3,3,3-trifluoro-1-propen-1-yl)
A pyrethroid-based compound such as -2,2-dimethylcyclopropanecarboxylate; 1- (4-chlorophenyl) -3- (2,6-difluorobenzoyl) urea,
1- [3,5-dichloro-4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenyl] -3
-(2,6-difluorobenzoyl) urea, 1-
(3,5-dichloro-2,4-difluorophenyl)-
Benzoyl urea compounds such as 3- (2,6-difluorobenzoyl) urea; 2-tert-butylimino-
3-Isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-1,3,5-thiadiazin-4-one, trans-5- (4-chlorophenyl) -N-cyclohexyl-4-methyl- 2-oxothiazolidinone-
Compounds such as 3-carboxamide, N-methylbis (2,4-xylyliminomethyl) amine, N '-(4-chloro-o-tolyl) -N, N-dimethylformamidine; isopropyl (2E, 4E) -11-methoxy-
Juvenile hormone-like compounds such as 3,7,11-trimethyl-2,4-dodecadienoate; Other compounds include dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, and the like. To be Furthermore,
It is also possible to mix and use together with microbial pesticides such as BT agents and insect pathogenic virus agents.

For example, germicides include S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S.
-Organophosphorus compounds such as diphenylphosphorodithioate and aluminum ethyl hydrogen phosphonate; organochlorine compounds such as 4,5,6,7-tetrachlorophthalide and tetrachloroisophthalonitrile;
Manganese ethylene bis (dithiocarbamate) polymer, zinc ethylene bis (dithiocarbamate)
, A complex of zinc and manneb, a dithiocarbamate compound such as a polymer of dizinc bis (dimethyldithiocarbamate) ethylene bis (dithiocarbamate), zinc propylenebis (dithiocarbamate); 3a, 4, 7, 7a -Tetrahydro-N- (trichloromethanesulfenyl) phthalimide, 3a, 4
N-such as 7,7a-tetrahydro-N- (1,1,2,2-tetrachloroethanesphenyl) phthalimide, N- (trichloromethylsulfenyl) phthalimide
Halogenothioalkyl compounds; 3- (3,5-dichlorophenyl) -N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide, (RS) -3-
(3,5-Dichlorophenyl) -5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione, N-
Dicarboximide compounds such as (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide; methyl 1- (butylcarbamoyl) benzimidazol-2-yl carbamate, dimethyl 4, Benzimidazole compounds such as 4 '-(o-phenylene) bis (3-thioallophanate);
1- (4-chlorophenoxy) -3,3-dimethyl-1
-(1H-1,2,4-triazol-1-yl) butanone, 1- (biphenyl-4-yloxy) -3,3-
Dimethyl-1- (1H-1,2,4-triazole-1
-Yl) butan-2-ol, 1- [N- (4-chloro-2-trifluoromethylphenyl) -2-propoxyacetimidoyl] imidazole, 1- [2- (2,4
-Dichlorophenyl) -4-ethyl-1,3-dioxolan-2-ylmethyl] -1H-1,2,4-triazole, 1- [2- (2,4-dichlorophenyl) -4-
Propyl-1,3-dioxolan-2-ylmethyl]-
1H-1,2,4-triazole, 1- [2- (2,4
-Dichlorophenyl) pentyl] -1H-1,2,4-
Azole compounds such as triazole; 2,4'-dichloro-α- (pyrimidin-5-yl) benzhydryl alcohol, (±) -2,4'-difluoro-α- (1
Carbinol compounds such as H-1,2,4-triazol-1-ylmethyl) benzhydryl alcohol;
3'-isopropoxy-o-toluanilide, α, α, α
Benzanilide compounds such as -trifluoro-3'-isopropoxy-o-toluanilide; methyl N-
(2-Methoxyacetyl) -N- (2,6-xylyl)
An acylalanine-based compound such as -DL-alaninate; 3-chloro-N- (3-chloro-2,6-dinitro-4-α, α, α-trifluorotolyl) -5-trifluoromethyl-2- Pyridinamine compounds such as pyridinamine; Other compounds include piperazine compounds, morpholine compounds, anthraquinone compounds, quinoxaline compounds, crotonic acid compounds, sulfenic acid compounds, urea compounds, antibiotics, etc. To be

The insecticidal, acaricidal, nematicidal, and soil-pesticidal composition of the present invention is effective for controlling various harmful insects, harmful mites, harmful nematodes, harmful soil pests, and its application is generally 1 to 20000.
ppm The concentration of the active ingredient is preferably 20 to 2000 ppm. The concentrations of these active ingredients can be appropriately changed depending on the form of the preparation, the method of application, the purpose, the time, the place, the state of occurrence of harmful insects and the like. For example, in the case of aquatic pests, it can be controlled even by spraying a drug solution having the above-mentioned concentration range to the place of occurrence, and therefore the active ingredient concentration range in water is below the above. The amount applied per unit area is about 0.1 to 5000 g, preferably 10 to 1000 g as an active ingredient compound per 10 a.
Is used. However, it is possible to deviate from these ranges in special cases.

Application of various formulations containing the compound of the present invention, or a dilution thereof, is a generally applied application method, that is, spraying (for example, spraying, spraying, misting, atomizing, granulation, water surface application, etc.), It can be performed by soil application (mixing, irrigation, etc.), surface application (application, dressing, coating, etc.), immersion poison bait and the like. It is also possible to feed livestock by mixing the above-mentioned active ingredient with feed to control the development and growth of harmful insects, especially harmful insects, in the excrement. It can also be applied by a so-called ultra low volume small amount application method (ultra low volume). In this way it is possible to contain 100% of the active ingredient.

Test Example 1 Each formulation of active ingredient compound was dispersed in water, and
The concentration was adjusted to 00 ppm. What left only one primary leaf of common bean was transplanted into a cup (7 cm in diameter, 4 cm in height), and about 30 larvae of Nymphalid mite were inoculated into this.
This is immersed in the chemical solution of the predetermined concentration for about 10 seconds,
After air-drying, it was left to stand in a 26 ° C. illuminated thermostat. On the second day after the treatment, life or death was judged, and the miticidal rate was calculated by the following calculation formula, all the active ingredient compounds NO.1 to 4 were 100%.
Met.

Test Example 2 Each formulation of the active ingredient compound was dispersed in water to prepare 8
The leaf pieces of cabbage were soaked in a chemical solution adjusted to a concentration of 00 ppm for about 10 seconds and air-dried. A wet filter paper was laid on a Petri dish with a diameter of 9 cm, and air-dried leaf pieces were placed on it. Two to three instar larvae of Plutella xylostella were released there, covered with a lid, and allowed to stand in a 26 ° C illuminated thermostat. On the second day after the insect was released, it was judged whether it was alive or dead,
The mortality was calculated by the following formula, and the results shown in Table 3 were obtained.

Test Example 3 A test was conducted in the same manner as in Test Example 2 except that the 2nd to 3rd-aged diamondback moth was replaced with the 2nd to 3rd-old Monascus, and the results shown in Table 4 were obtained.

Test Example 4 Rice seedlings were dipped in a chemical solution adjusted to have an active ingredient concentration of 800 ppm for about 10 seconds, air-dried, and the roots were wrapped with moistened absorbent cotton and placed in a test tube. Then, 10 adult brown planthoppers were released into this, the tube mouth was covered with gauze, and 26
It was left in an incubator with illumination at ℃. On the second day after the release of the insects, life or death was determined, and the mortality rate was calculated in the same manner as in Test Example 2, and the results shown in Table 5 were obtained.

Test Example 5 Sweetpotato rootworm nematode contaminated soil 1/14000
It was filled in an R pot and a chemical solution adjusted to have an active ingredient of 250 g / a was irrigated. On the second day after the treatment, all layers of the treated soil were mixed and tomato seedlings at the 3-4 leaf stage were transplanted. When 20 days after the treatment with the chemical solution, the degree of fecal growth of cats was investigated, all the active ingredient compounds NO. 1 to 4 completely suppressed the cattle colonization.

Test Example 6 Each formulation of the active ingredient compound was dispersed in water, and cabbage leaf pieces were immersed in a drug solution adjusted to a predetermined concentration for about 10 seconds and air dried. A wet filter paper was laid on a Petri dish with a diameter of 9 cm, and air-dried leaf pieces were placed on it. The peach moss aphid wingless nymphs were released there, and the lid was covered and left in a 26 ° C. illuminated incubator. On the 2nd day after the release of insects, life or death was determined, and the mortality rate was obtained in the same manner as in the case of Test Example 2, and the results shown in Table 6 were obtained.

Test Example 7 Each formulation of the active ingredient compound was dispersed in water and adjusted to a predetermined concentration. Transplanting only one primary leaf of kidney bean into a cup (7 cm in diameter, 4 cm in height),
This was inoculated with about 30 larvae of Dicofol- and organophosphorus drug-resistant flesh mites. This was immersed in the chemical solution adjusted to the above predetermined concentration for about 10 seconds, air-dried, and then left in a constant temperature oven with lighting at 26 ° C. Life or death was determined on the second day after the release, and the acaricidal rate was determined in the same manner as in Test Example 1 above.
The results shown in Table 7 were obtained.

Test Example 8 Each formulation of the active ingredient compound was dispersed in water to give 8
The concentration was adjusted to 00 ppm. Seedlings of two primary leaves of common bean were transplanted to a cup (diameter 7 cm, height 4 cm), and 10 ml of the chemical solution adjusted to the predetermined concentration was soil-irrigated. Two days after the treatment, about 30 larvae of Dicofol- and organophosphorus-drug-resistant spider mites were inoculated on the leaves and left in a 26 ° C. illuminated thermostat. On the second day after the insect was released, it was judged whether it was alive or dead,
The acaricidal rate was calculated in the same manner as in Test Example 1,
The results in the table were obtained.

Test Example 9 40 g of air-dried soil was placed in an ice cream cup, and 10 ml of a chemical solution adjusted to a concentration of 500 ppm was poured into the cup and mixed uniformly. After 24 hours of mixing, onion pieces were embedded in the soil as baits, and 10 third-instar larvae of the onion fly were released therein and left in a lighted thermostat at 26 ° C. After 7 days from the release of insects, life and death were investigated, and the mortality rate was calculated in the same manner as in the case of Test Example 2. All of the active ingredients NO.

Next, formulation examples of the compound of the present invention are described below.

Formulation Example 1. (A) Compound No. 1 20 parts by weight (b) N. N'-dimethylformamide 72 parts by weight (c) Polyoxyethylene alkyl phenyl ether 8 parts by weight The above components are uniformly mixed and dissolved to obtain an emulsion.

Formulation example 2. (A) 5 parts by weight of compound NO.2 (b) 95 parts by weight of talc The above ingredients are uniformly mixed to obtain a powder.

Formulation example 3. (B) Compound NO.4 ^- 0.50 parts by weight (b) polyoxyethylene octylphenyl ether 0.15 parts by weight (c) phosphoric acid esters of polyoxyethylene 0.10 parts by weight (d) particulate calcium carbonate 99.25 By weight, (a) to (c) are uniformly mixed in advance, diluted with an appropriate amount of acetone, and then sprayed on (d) to remove acetone to obtain a granule.

Formulation example 4. (A) Compound NO.3 50 parts by weight (b) Fine silica 15 parts by weight (c) Fine clay 25 parts by weight (d) Sodium naphthalene sulfonate formalin condensate 2 parts by weight (e) Dialkylsulfosuccinate 3 parts by weight ( F) Polyoxyethylene alkyl allyl ether sulphate 5 parts by weight The above ingredients are uniformly mixed and pulverized to obtain a wettable powder.

Formulation example 5. (A) 5 parts by weight of compound NO.4 (b) 5 parts by weight of glycerin (c) 3 parts by weight of milk powder (d) 87 parts by weight of fish meal The above ingredients are uniformly kneaded to obtain a paste.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kiyomi Yoshida 2-3-1 Nishishibukawa, Kusatsu City, Shiga Ishihara Sangyo Co., Ltd. Central Research Institute (72) Inventor Osamu Imai 2-3 Shibukawa, Kusatsu City, Shiga Prefecture Number 1 Ishihara Sangyo Co., Ltd. Central Research Institute Examiner Reiko Imamura

Claims (3)

[Claims] 1. A general formula: (In the formula, R ₁ and R ₂ are alkyl groups, R ₃ is an alkyl group which may be substituted with a hydrogen atom or a halogen atom, and n is an integer of 2 to 6) Compound. 2. A general formula: (In the formula, R ₁ and R ₂ are alkyl groups, R ₃ is an alkyl group which may be substituted with a hydrogen atom or a halogen atom, and n is an integer of 2 to 6) An insecticidal, acaricidal, nematicidal, and soil-killing pesticide, which comprises at least one compound as an active ingredient. 3. A general formula: (Wherein R ₃ is a hydrogen atom or an alkyl group which may be substituted with a halogen atom, and n is an integer of 2 to 6), and a general formula: (Wherein Hal is a halogen atom and R ₁ and R ₂ are alkyl groups) are reacted with a compound represented by the general formula: (In the formula, R ₁ , R ₂ , R ₃ and n are as described above)
A method for producing an organophosphorus compound represented by: