JPS624295A - Organic phosphorus based compound and insecticide, acaricide and nematocide containing said compound - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I [X is formula II (X1 is H, alkyl or alkoxycarbonyl; X2 is O or S; Y is O or -CH2-), formula III (X3 is -CH2-, O or S) or formula IV; R1 and R2 are alkyl; Z is O or S]. EXAMPLE:O-Ethyl S-sec-butyl(2-oxo-1-pyrrolidinyl)phosphonothiolate. USE:An insecticide, acaricide and nematocide. PREPARATION:A compound expressed by the formula XH, e.g. tetrahydro-1,3- thiazin-2-one, is reacted with a phosphoric acid diester chloride based compound expressed by formula V, e.g. O-ethyl S-sec-butylthiophosphoryl chloride, in the presence of an acid acceptor, e.g. n-butyl lithium, and a solvent, e.g. THF, preferably at -80 deg.C - room temperature.

Description

Detailed Description of the Invention (Field of Industrial Application) The present invention relates to novel organophosphorus compounds that exhibit effective control action against harmful insects, mites, and nematodes, methods for producing them, and This invention relates to insecticides, acaricides, and nematicides containing nuclear compounds as active ingredients.

(Disclosure of the Invention) The compound of the present invention is represented by the following general formula (I), and is an alkyl group or an alkoxycarbonyl group, X is an oxygen atom or a sulfur atom, Y is an oxygen radical, and 2 is an alkyl group or an alkoxycarbonyl group. In the general formula (I), the alkyl group represented by XI and the alkyl moiety of the alkoxycarbonyl group, and the alkyl group represented by ya and ya include methyl, ethyl, propyl, pudelle, etc. can be mentioned.

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

(X) (m) (I) (wherein, X
The reaction is usually carried out at a temperature range of -100 to 50°C, preferably 0°C to room temperature.

In addition, this reaction is carried out in the presence of an acid acceptor, and acid acceptors include organic lithium compounds such as n-butyllithium, tert-butyllithium, and phenyllithium, sodium hydroxide, potassium hydroxide, and hydrogenated Examples include inorganic bases such as sodium and potassium hydride, and organic bases such as triethylamine and pyridine. Furthermore,
These reactions are preferably carried out in the presence of a solvent,
Examples of solvents include aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; cyclic or acyclic aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as diethyl ether, dioxane, and tetrahydrofuran; niacetonitrile, propionitrile; , aa
Examples include nitrites such as crylonitrile, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide, sulfolane, and hexamethylphosphoric triamide.

Among the starting materials represented by the general formula (11), Xs
is a hydrogen atom, for example, by the following method,
Can be adjusted.

2-Pyrrolidino/Perichte, Volume 22, Page 3338ζ
In the two described methods, 2-pyrrolidine-thione is converted into Belihif. 38 volume, p. 1592, 3-isoxazolidinone was prepared by the method described in Journal Opu Chemical Society, vol. 22, p. 76 (1957), and 2-piperidinone was prepared by the method described in Berichte, vol. 21, p.
Page 2240: In the two described methods, the cabbage blocktum can be synthesized by Organic Synthesis Collective Volume,! , 371, tetrahydro-1,3-oxadi/-2-one is prepared in German Patent No. 858
, 402 (2) by the method described in Tetrahydro-1
, 3-thiazin-2-one is disclosed in JP-A-57-175180.
No., JP-A-58-29775, JP-A-58-2977
It can be easily synthesized by the method described in No. 6.

Compounds in which XI is an alkyl group or an alkoxycarbonyl group can be easily prepared by introducing a substituent into the compound obtained by the above method using a conventional method.

Examples of specific compounds of the present invention are listed below.

Compound A1, 0-ethyl 5-sec-butyl (2-oxo-1-pyrrolidinyl)phosphonothiolet)
n”p=
1.5050 compounds 42.0-1ti/l/5-
sec-butyl(5-methyl-2-oxo-1-pyrrolidinyl)phosphonothiolate 82 = 1.4940 compounds & 3.0-ff-thkS-sec-butyl(2-oxo-1-piperidinyl)phosphonotiolate v −)
n2: Ij1 = 1.5016 Compound 44.0-Ethyl S -5ec-butyl (3-ethoxycarbonyl-2-okino-1-bi-periflu)phosphonothiolate Oil Compound 45
．． 0-ethyl 5-n-propyl (2-thioxo-1
-pyrrolidinyl)phosphonothiolate
n3B"= 1.5506 compound store 6.0-ethyl
S-5ec-butyl(3-oxo-2-ynoxazolidinyl)phosphonothiolet) n”7
58 = 1.4928 Compound A7.0-Ethyl S -
5ec-butyl(tetrahydro-2-oxo-3-oxazinyl)phosphonothiole) n”1)0=
1.5055 compound &8.0-ethyl 8-5ec-
Butyl (tetrahydro-2-oxo-3-thiazinyl)
Phosphonothiolate n2 i0 = 1.5315 Compound A9.0-Ethyl S -5ec-butyl (2-oxo-1-hexahydroazepinyl) phosphonothiole)
n236-1.4978 compound l610.
O-ethyl S-propyl (3-oxo-2-isoxazolidinyl)phosphonof-)
n"fi'-1,4940 Next, a synthesis example related to the compound of the present invention will be described.

Synthesis Example 1. Synthesis of 0-ethyl S-5ec-butyl (tetrahydro-2-oxo-3-thiazinyl)phosphonothiolate.

1.72 of tetrahydro-1,3-thiazin-2-one was dissolved in 30 ml of tetrahydrofuran and then cooled to -78°C. Thereto, 11.2 m (1.55 molar concentration) of a hexane solution of (2n-butyllithium) was gradually added dropwise, followed by continued stirring at the same temperature for 15 minutes. Next (20-ethyl S -5ec- A 10-liter solution of tetrahydrofuran containing 3.5 f of butylthiophosphoric acid chloride was gradually added dropwise, and the mixture was allowed to react for 2 hours while gradually returning to room temperature.

After the reaction was completed, the reaction product was poured into ice water, and ethyl acetate was added to perform extraction. The extracted layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel chromatography to give a refractive index (n2, 3.0) of 1.5315.
0-ethyl 5-sec-butyl (tetrahydro-2-
Oxo-3-thiazinyl)phosphonothiole)2.7F
I got it.

Synthesis Example 2. Synthesis of 0-ethyl S -5ee-butyl (2-oquino-1-pyrrolidinyl)phosphonothiolate.

2-pyrrolidone 1. Of was diluted with tetrahydrofuran in 1-screw H, -78°C (=after cooling, n-butyllithium n
7.2 d of -hexane solution (1.65 molar concentration) was added dropwise and stirred for 15 minutes while maintaining the temperature at -78°C. Subsequently, 2.65 t of 0-ethyl S-5ec-butylthiophosphoric acid chloride was dissolved in tetrahydrofuran 5- and added dropwise at the same temperature, and the mixture was gradually warmed to room temperature and reacted at room temperature for 2 hours.

After the reaction was completed, the reaction product was poured into saturated brine and extracted with ethyl acetate. The extract was dried with anhydrous sodium sulfate,
After distilling off the ethyl acetate, it was purified by silica gel chromatography, and the refractive index (n132) was 1.5050+7.
)O-:! -f8-sec-butyl(2-oxo-1
-pyrrolidinyl)phosphonothiolate 1. I got Of.

The compound of the present invention exhibits excellent activity as an active ingredient of insecticides, insecticides, acaricides, and nematicides as shown in the test examples described below. For example, plant parasitic mites such as two-spotted spider mite, false red spider mite, citrus spider mite, etc., diamondback moth, fall armyworm, fall armyworm, cordling moth, ballworm (no Japanese name),
Tobacco batworm (no Japanese name), gypsy moth, Colorado potato beetle, poleweed beetle (Japanese name sushi), aphids, planthoppers, leafhoppers, scale insects, stink bugs, mealybugs, thrips, grasshoppers, wasp flies, Agricultural pests such as scarab beetles, red beetles, capryal moths, etc., house dust mites, roaches, house flies,
Public sanitary pests such as Culex pipiens, thrips, grain storage pests such as cornstarch, clothing and house pests such as burs, cutworms, termites, etc.
Other humans, livestock, etc.: parasitic fleas, lice,
It is also effective against flies, etc.
It is also effective against plant-parasitic nematodes such as the pine-nosed beetle. Also, Dicofol (Dicofol)
) and are also effective against pests such as organophosphate-resistant plant parasitic mites, organophosphate-resistant aphids, and houseflies. Furthermore, since the compound of the present invention has excellent permeability, it is possible to simultaneously control soil pests and nematodes by treating the soil with the compound of the present invention.
It can also control pests on the two stem and leaf parts.

When using the compound of the present invention as an active ingredient in insecticides, acaricides, and nematocides, it can be used in emulsions, powders, granules, wettable powders, solutions, etc. together with pesticide adjuvants, as in the case of conventional pesticide formulations.
It can be formulated into various forms such as aerosols and pastes. These compounding ratios are usually active ingredients 05~
The agricultural chemical adjuvant is 10 to 99.5 parts by weight in 90 parts by weight.

When these preparations are actually used, they can be used as they are, or they can be diluted to a predetermined concentration with a diluent such as water.

The agrochemical auxiliary agents mentioned herein include carriers, emulsifiers, suspending agents, dispersants, spreading agents, penetrants, wetting agents, thickeners, stabilizers, etc., and may be added as appropriate if necessary. The carriers are divided into solid carriers and liquid carriers (solid carriers include starch, activated carbon, soybean flour, wheat flour, wood flour, fish meal,
Examples include animal and vegetable powders such as powdered milk, mineral powders such as Merck, kaolin, bentonite, calcium carbonate, zeolite, diatomaceous earth, white carbon, clay, alumina, sulfur powder, etc. Liquid carriers include water, methyl alcohol, and ethylene. Alcohols such as glycols, keto/groups such as acetone and methyl ethyl ketone, ethers such as dioxane and tetrahydrofuran, aliphatic hydrocarbons such as kerosene and kerosene, aromas such as xylene, trimethylbenzene, tetramethylbenzene, cyclohexane, and solvent naphtha. group hydrocarbons, halogenated hydrocarbons such as chloroform and chlorobenzene, acid amides such as dimethylformamide, esters such as ethyl acetate and glycerin ester of fatty acids, nitriles such as acetonitrile, and sulfur-containing compounds such as dimethyl sulfoxide. Examples include the following.

In addition, other agricultural chemicals such as insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, herbicides,
It can be mixed or used in combination with plant growth regulators, etc., and in this case (sometimes even more excellent effects may be shown).

For example, as an insecticide, acaricide, or nematocide, 0-(4-promo-2-chlorophenyl)0-ethyl
S-propyl phosphorothioate, dimethyl 2.2-
Dichlorovinyl phosphate, ethyl-3-methyl-4
-(methylthio)phenyl(isopropyl)phosphoramidate, 0.0-dimethyl 0-(4-nitro-m-
) lyl) phosphorothioate, 0-ethyl 0-4-nitrophenyl phenylphosphonothioate, 0,O-diethyl 0-(2-isopropyl-6-methyl-pyrimidin-4-yl)phosphorothioate, 0.0-dimethyl O -(3,5,6-Dolichlor 2
, -pyridyl) phosphorothioate, 0,S-dimethyl acetyl phosphoramidothioate, 0-(2,4-dichlorophenyl)〇-ethyl S-propyl phosphorodithioate, 1 -naphthyl
Methyl carbamate, 2-(1-impropoxy)phenyl methyl carbamate, 2-methyl-2-(methylthio)probionaldehy)
'O-(methylcarbamoyl)oxime, 2,3-dihydro-2,2-dimethylbenzofuran-7
-yl methyl carbamate, bisC(N-(1-methylthio)ethylideneaminooxycarbonyl)-N-methylaminocosulfide, S-methyl N-C(methylcarbamoyl)oxycothioacetimidate, N,N-dimethyl -2-methylcarbamoyloxyimino-2-(methylthio)acetamide, 2-C(ethylthio)methyl]phenyl methylcarbamate, 2-dimethylamino-5,6-dimethylpyrimidine-4
-yl-dimethylcarbamate, 2.2.2-) dichloro-1,1-bis(4-chlorophenyl)ethanol, 4-chlorophenyl-2,4,5-) IJ dichloroenyl sulfone, organochlorine compounds such as tricyclohexyltine hydroxide;・Trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane
Carboxylate, (±) α-cyano-3-phenoxybenzyl (±) cis-trans 3-(2,2-dichloroviny)-2*2-dimethylcyclopropane Carboxylate, (S)-α-cyano-m -Phenoxybenzyl (1 & 3
R)-3-(2,2-dibromonovinyl)-2,2-
Dimethylcyclopropane carboxylate, (RS)-α-cyano-3-phenoxybenzyl (I
RS)-cis-5-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropane carboxylate, pyrethroid compounds such as 1-(4-chlorophenyl)-3- (2,6-difluorobenzoyl)urea, 1-(3,5-dichloro-4-(5-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)-
3-(2,6-difluorobenzoyl)urea, 1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea, 2 -tert-butylimino-3-isopropyl-5
-Phenyl-3,4,5,6-titrahydro2H-
1,3,5-thiadiazin-4-one, 4-methyl-3
-(4-chlorophenyl)-3-cyclohexyl-carbamoyl-2-thiazolidone, N-methylbis(2,4-xylyliminomethyl)amine, isopropyl(2B,4E)-11-methoxy-3° 7.11-) dimethyl-2,4-dodecadienoate, a juvenile hormone-like compound, and other compounds such as dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, etc. It will be done. Furthermore, it can also be used in combination with biological pesticides such as BT agents.

For example, the fungicides include S-benzyl 0,0, sopropyl phosphorothiolate, and ethyl S.

S-diphenylphosphorodithioate, aluminum
Organophosphorus compounds such as ethyl hydrogen phosphonate; Organochlorine compounds such as 4.5,6.7-7'''trachlorophthalide, tetrachloroinphthalonitrile; Manganese ethylene bis(dithiocarbamate) , zinc ethylene bis(dithiocarbamate)
, complex compound of zinc and maneb, zinc polymer of didizinc bis(dimethyldithiocarbamate) ethylene bis(dithiocarbamate), propylene bis(dithiocarbamate), N-(dichloromethylthio)cyclohexene-1,2-dicarboximide, N
-(1,1,2,2-tetrachloroethylthio)-4
-cyclohexene-1,2-dicarboximide, N-(
) Dichloromethylthio)phthalimide Yorina N-71
0 Genothioalkyl compound: 3-(3,5-dichlorophenyl)-N-iapropyl-2,4-dioxoimidazolidine-1-carboxamide, 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine -2,4-dione, N-(3,5-dichlorophenyl) -1,2-dimethyl-cyclopropane-1,2-
Dicarboximide compounds such as dicarboxylate;
Benzimidazole-based compounds such as methyl 1-(butylcarbamoyl)-2-benzimidazole carbamate, dimethyl 4.4'-(0-phenylene)bis(3-thioallophane-); 1-(4-chlorophenoxy)- 3,3-C) f-1-(IH-1,2,4-
) riazol-1-yl)butanone, 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(IH-
1,2,4-)riazol-1-yl)butan-2-ol, 1(N-(4-chloro-2-trifluoromethyrophenyl)-4-ethyl-1,3-dioxolane-2
-ylmethyl) -1H-1,2,4-triazole,
1-(2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl) -1H
-1,2,4-) lyazole, 1-(2-(2,4-dichlorophenyl)penal]-II(-1,2,4-)
Azole compounds such as lyazole; (±) −2,
4'-dichloro-α-(pyrimidin-5-yl)benzhydryl alcohol, (±)-2,4'-difluoro
-a-(l H-1.

2.4-) Carbinol compounds such as lyazol-1-ylmethyl)benzhydryl alcohol; 3'-
Benzanilide-based compounds such as isopropoxy-2-methylbenzanilide, 3'-isopropoxy(α,α-trifluoro-〇-)ylanilide; methyl N-(2-
methoxyacetyl)-N-(2,6-xylyl)-DL
-alaninate, dimethyl-N-acylanilide-based compounds, 3-chloro-N-(3-chloro-2,6-sinitro-4-αZcL, α-trifluorotolyl) 5-trifluoromethyl-2-pyridinamine, etc. Other aniline compounds include m-piperazine compounds; mole 7-olin compounds; anthraquinone compounds; quinoxaline compounds; crotonic acid compounds; sulfenic acid compounds; urea compounds; and antibiotics.

□ The insecticide, acaricide, and nematicide of the present invention are effective in controlling various harmful insects, harmful mites, and harmful nematodes,
Application is generally (-1 to 20,000 ppm, preferably 2
Active ingredient concentrations of 0 to 2,000 ppm are dangerous.

The concentration of these active ingredients can be changed as appropriate depending on the form of the preparation, the method of application, purpose, timing, location, pest outbreak status, etc. For example, in the case of harmful aquatic insects, the concentration range of the active ingredient in water is below the above range, since it is possible to control aquatic pests by spraying a chemical solution with the above concentration range to the place of occurrence. The application amount per unit area is 101 equivalents, and the active ingredient compound is about 0.1 to 5 poor, preferably 10 to 1,000
f is used. However, in special cases it is also possible to depart from these ranges.

Various formulations containing the compounds of the present invention or dilutions thereof can be applied by commonly used application methods, such as scattering (e.g., scattering, spraying, misting, atomizing, dusting, water surface application, etc.); It can be applied by soil application (mixing, irrigation, etc.), surface application (painting, dusting, coating, etc.), dipped bait, etc. Furthermore, it is also possible to mix the above-mentioned active ingredients in the feed of livestock to keep them alive and to control the emergence and growth of harmful insects, especially harmful insects, in their excrement. In addition, the so-called ultra-high concentration small amount spraying method (ultra low-v
olume) can also be applied. In this way it is possible to contain ioo % of active ingredient.

Test Example 1゜Each formulation of active ingredient compounds A1 to 10 was added to water (=
It was dispersed and adjusted to a concentration of soo ppm.

Cup of kidney bean with only one first leaf left (
They were transplanted into 7 wounds in diameter and 4 cm in height, and about 30 young adult two-spotted spider mites were inoculated into these. This product was immersed in the chemical solution adjusted to the predetermined concentration for about 10 seconds, and after air drying,
Two devices were placed in a thermostatic chamber with lighting at ℃. The survival rate was determined on the second day after the insects were released, and the mortality rate was calculated using the following calculation formula (2).
Met.

Number of insects released test example 2゜ Each formulation of active ingredient compounds 1 to 3 and 6 to 7 was dispersed in water, and cabbage leaf pieces were immersed for about 10 seconds in each drug solution adjusted to a concentration of soo ppm. ,
Air dried. Diameter 9c! An f1 Petri dish was lined with moist filter paper, and air-dried leaf pieces were placed on top of it. 2nd to 3rd instar diamondback moth larvae were released there, the lid was placed, and the container was left in a lighted incubator at 26°C. The survival rate was determined on the second day after the insects were released, and the mortality rate was determined in the same manner as in Test Example 1.
%Met.

Test Example 3゜For active ingredient compounds &1 to 3, 7 and 8, concentration 80
Rice seedlings were immersed in a chemical solution adjusted to 0 ppm for 10 seconds, air-dried, wrapped around the roots with absorbent cotton, and placed in a test tube. Next, 10 adult brown planthoppers were released into the tube, and the tube was covered with gauze. Two days later, the insects were examined to see if they were alive or dead, and the mortality rate was determined in the same manner as in Test Example 1. All of the insects were found to be Zoo%.

Test example 4゜115,000 sweet potato cob centimeter contaminated soil
A R pot was filled, and a predetermined amount of each drug solution adjusted to have an active ingredient compound A1-4, 5, and 7 at 250 f/a was irrigated. Two days after the chemical solution treatment, the entire layer of the ζyu-treated soil was mixed, and tomato seedlings at the 3rd to 4th drug stage were transplanted. 20 days after the chemical solution treatment (the degree of Ninecop settlement was investigated, and the results shown in Table 1 were obtained).

The degree of Nekobu settlement was determined according to the following criteria.

0 No catopsis 1 L small 2 〃 Medium 3 〃 Large 4 〃 Very large Table 1 Test example 5゜ Active ingredient compound A Each formulation of 1, 3, 4.7 and 9 was dispersed in water and the prescribed concentration was To the chemical solution adjusted to
Cabbage leaf pieces were soaked for about 10 seconds and air dried. Diameter 9
A Petri dish (2) with moist filter paper and air-dried leaf pieces placed on top of it. Release the wingless viviparous females of the green peach aphid into the Petri dish, cover with a lid, and keep in a thermostatic chamber with lighting at 26°C. The insects were left to stand. The survival rate was determined on the second day after the insects were released, and the mortality rate was determined in the same manner as in Test Example 1. All of them were 100%.

Test Example 6 The respective formulations of active ingredient compounds A1.2 and 5 to 7 were dispersed in water and adjusted to a predetermined concentration. One primary leaf of common bean with a stubble left was transplanted into a cup (diameter 7, height 4 crs), and about 30 larvae of two-spotted spider mites resistant to dicofol and organophosphorus were inoculated into the cup.

This product was immersed in the chemical solution adjusted to the predetermined concentration for about 10 seconds, air-dried, and then placed in an illuminated constant temperature chamber at 26°C.

On the second day after the insects were released, the insects were determined to be alive or dead, and the mortality rate was determined in the same manner as in Test Example 1. The results shown in Table 2 were obtained.

Test Example 7゜Each formulation of active ingredient compound &2 and 5 was added to water;
The concentration (=adjusted) was 1001) pm. A seedling of two primary leaves of common bean was transplanted into a cup (diameter 73, height 4 cm), and the drug solution 1O- was added to the prescribed concentration (2 adjusted). The soil was irrigated. Two days after the treatment, about 30 young adult two-spotted spider mites resistant to dicofol and organophosphorus were inoculated in the eastern part and left in a lighted incubator at 26°C.

The insects were monitored on the second day after release to determine whether they were alive or dead, and the mortality rate was determined in the same manner as in Test Example 1.0, and all were found to be Zoo%.

Next, formulation examples of the compounds of the present invention will be described below.

Formulation example 1゜(a) Compound A1 20 parts by weight (b)
72 parts by weight of N,N'-dimethylformamide (c) phosphoryoxyethylene alkylphenyl ether
8 parts by weight or more were uniformly mixed and dissolved to form an emulsion.

Formulation example B (a) Compound &2 50 parts by weight (b)
Tetramethylbenzene 38 parts by weight (c) Mixed emulsifier of alkylbenzene sulfonate, polyoxyethylene alkylphenol ether and polyoxyethylene phenylphenol ether (trade name Agelisil P
-311° Kao Soap (manufactured by Kao Soap ■) 12 parts by weight or more were homogeneously mixed and dissolved to form an emulsion.

Formulation example 3゜(a) Compound shop 3 85 parts by weight (b)
15 parts by weight or more of the mixed emulsifier used in Formulation Example 2 was uniformly mixed to form a high concentration emulsion.

Formulation example 4゜(a) Compound 45 5 parts by weight (b)
Merck 95 parts by weight or more were uniformly mixed to make a powder.

Formulation Example 5゜(a) Compound Jf & 7 5 parts by weight (b) Bentonite 45 parts by weight (c) 150 parts by weight or more of Kaori with a small amount of water (mixture, extrusion molded into granules, dried to form granules) And so.

Formulation example 6゜(a) Compound M3 0.50 parts by weight (
b) Pholioxyethyle/octylphenyl ether
0.15 parts by weight (c) Polyoxyethylene phosphoric acid ester 0.10 parts by weight (d) Granular calcium carbonate 99.25 parts by weight (
A) - (Han) were mixed uniformly in advance, diluted with an appropriate amount of acetone, and then sprayed on (d) to remove acetate and form granules.

Formulation example 7゜(a) Compound A6 50 parts by weight (b)
Fine powder silica 15 parts by weight (c) Fine powder clay 25 parts by weight (d) Naphthalene sulfonic acid soda formalin condensate
2 parts by weight (E) 3 parts by weight of dialkyl sulfosuccinate (H) Polyoxyethylene alkyl allyl ether sulfate 5 parts by weight or more
Up to = mixed and pulverized to make a wettable powder.

Formulation example 8゜(a) Compound A7 5 parts by weight (b)
Glycerin 5 parts by weight (c) powder
Milk 3 parts by weight (2 parts fish powder)
87 parts by weight or more were mixed uniformly to form a paste.

Formulation example 9゜(a) Compound A8 10!it part (b) Polyoxyethylene octylphenyl ether
3 parts by weight (c) Kerosene
87 parts by weight or more were uniformly mixed and dissolved to form a spray that can be atomized 1* with compressed air.

Claims (1)

[Claims] 1. General formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Group (X
_1 is a hydrogen atom, an alkyl group, or an alkoxycarbonyl group, X_2 is an oxygen atom or a sulfur atom, and Y is an oxygen atom or a -CH_2- group) is as described above, and
_3 is -CH_2- group, oxygen atom or sulfur atom)
or an organic phosphorus compound represented by a ▲ group (where X_1 is as described above), R_1 and R_2 are an alkyl group, and Z is an oxygen atom or a sulfur atom]. . 2. General formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Group (X
_1 is a hydrogen atom, an alkyl group, or an alkoxycarbonyl group, X_2 is an oxygen atom or a sulfur atom, and Y is an oxygen atom or a -CH_2- group) is as described above, and
_3 is -CH_2- group, oxygen atom or sulfur atom)
or an organic phosphorus compound represented by a ▲ group (where X_1 is as described above), R_1 and R_2 are an alkyl group, and Z is an oxygen atom or a sulfur atom]. An insecticide, acaricide, or nematocide containing at least one of the following as an active ingredient. 3. General formula: XH [In the formula,
_1 is a hydrogen atom, an alkyl group, or an alkoxycarbonyl group, X_2 is an oxygen atom or a sulfur atom, and Y is an oxygen atom or a -CH_2- group) is as described above, and
_3 is -CH_2- group, oxygen atom or sulfur atom)
or ▲There are mathematical formulas, chemical formulas, tables, etc.▼groups (X_1 is as described above)] and general formulas: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R_1 and R_2 is an alkyl group, and Z is an oxygen atom or a sulfur atom. Z, R_1 and R_2 are as described above.