JPH0254323B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a composite insecticide that exhibits excellent biological activity. More specifically, 2-methoxy-4-(2-methoxyphenyl)-1,3,4-oxadiazolin-5-one and one or two organic phosphorus compounds
The present invention relates to a composite insecticide characterized by containing more than one type of insecticide as an active ingredient. The active ingredient of the present invention, 2-methoxy-4-(2-
methoxyphenyl)-1,3,4-oxadiazolin-5-one (hereinafter referred to as compound A) is described in JP-A-51-101981 as an oxadiazolinone derivative having the following general formula, and that they are It is described as having insecticidal, acaricidal and nematocidal effects. [Wherein, R is an alkyl group having 1 to 4 carbon atoms,
R ₁ is an alkyl group having 2 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms in the alkyl portion, an alkylthio group having 1 to 4 carbon atoms in the alkyl portion, or a trifluoromethyl group. The organic phosphorus compound, which is an active ingredient, has an acetylcholine inhibitory effect, and is used as an agricultural insecticide or fungicide. In recent years, important pests of rice, such as planthoppers and leafhoppers, have become highly resistant to the organophosphorus compounds. This means that
This is because the above-mentioned organic phosphorous compounds have been widely used in large quantities for many years, and pest insects have developed resistance to these chemicals. It has been revealed that a major factor contributing to resistance is decreased sensitivity to cholinesterase organophosphorus compounds, which are the point of action. The present inventors aimed to develop a drug that exhibits excellent biological activity against a wide variety of pest insects and is capable of accurately controlling them, in order to solve the above-mentioned resistance problem and save labor in agricultural work. I did a lot of research. As a result, by mixing Compound A, which does not have a very remarkable inhibitory power on cholinesterase when used alone, with one or more specific organophosphorus compounds, it is possible to inhibit sap-sucking pests and other pests, such as Unexpected and extremely excellent control effect against planthoppers, leafhoppers, aphids, and stink bugs, especially against pests that have acquired resistance to them, such as resistant leafhoppers with reduced cholinesterase susceptibility. exhibiting a cooperative and synergistic insecticidal activity-enhancing effect that is unexpectedly superior to the effect exhibited when each of these active ingredients is applied alone;
Moreover, it was discovered that unexpectedly excellent residual effectiveness was exhibited. Furthermore, these unexpected and surprising effects such as activity, residual effect, resistance, and pest control activity can be exerted at lower doses than the usual doses of each single agent. It has been discovered that various benefits such as extension, stable control effect, labor saving, and economic efficiency can be achieved, and furthermore, advantages such as low toxicity and no phytotoxicity can be obtained. It is therefore an object of the present invention to provide new mixtures, especially complex insecticides. The organic phosphorus compound having an acetylcholine inhibitory effect used in the present invention is one or more of the following compounds. Dimethyl 4-methylthio-m-tolyl phosphorothionate (fenthion), S-[α-(ethoxycarbonyl)benzyl]dimethyl phosphorothiolothioate (phenthoate)
dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate (trichlorfon, abbreviated as trichlorfon), S-1,2-bis(ethoxycarbonyl)ethyldimethylphosphorothiolothionate (malathion) , malathion), S-2-ethylsulfinyl-1-methylethyldimethylphosphorothiolate (ESP), dimethyl S-(N-methylcarbamoylmethyl)
Phosphorothiorothionate (dimethoate, abbreviated as dimethoate), Ethyl P-nitrophenylphenylphosphonothionate (abbreviated as EPN), S-[2-methoxy-5-oxo-1,3,4
-diazolin-4-ylmethyl] dimethyl phosphorothiolothionate (methidathion, abbreviated as methidathion), diethyl 5-phenyl-3-isoxazolyl phosphorothionate (isoxathion, abbreviated as isoxathion), p-cyanoph enyldimethylphosphorothionate (abbreviated as CYAP), S-(N-ethoxycarbonyl-N-methylcarbamoylmethyl)diethylphosphorothiolothionate (mecarbam, abbreviated as mecarbam), 2-methoxy-4H-1, 3,2-Benzdioxaphosphorine 2-sulfide (salithion, abbreviated as salithion), dimethyl S-2-(1-methylcarbamoylethylthio)ethylphosphorothiolate (vamidothion, abbreviated as vamidothion), and O - Ethyl diphenyl phosphorodithiolate (edifenphos, abbreviated as edifenphos) As mentioned above, the composite insecticide of the present invention exhibits an excellent synergistic control effect at a dosage lower than the normally used dosage of each single agent. Furthermore, it has the advantages of expanding the insecticidal spectrum, extending the application period, achieving stable pest control effects, and saving labor and economic efficiency.
With many benefits. Furthermore, the composite insecticide of the present invention has low toxicity to warm-blooded animals and good affinity for higher plants, that is, it does not cause any chemical damage to cultivated plants at normal concentrations, so it is suitable for use in agriculture and horticulture. As a drug it can be used quite advantageously against damage to plants by pests. In the composite insecticide of the present invention, the ratio of compound A and the organophosphorus compound can be selected as appropriate, but preferably about 0.1 to about 10 parts by weight of the organophosphorus compound per 1 part by weight of compound A, more preferably about 10 parts by weight of the organophosphorus compound. ,
An example of a blending ratio is about 0.5 to about 5 parts by weight. Further, as an example of a mixed composition of three or four types, the total amount of the remaining two or three organic phosphorus compounds per 1 part by weight of compound A is about 0.1 to about 10 parts by weight, more preferably, in the case of three types. is about 1 to about 6
In the case of four types, it is desirable to mix about 3 to about 10 parts by weight. In addition, a mixed active ingredient compound depending on the target pest to be controlled may be appropriately contained in accordance with the above. When the active ingredient compound used in the present invention is used as an insecticide, it can be diluted directly with water and used, or it can be used in various ways using a pesticide auxiliary by a method commonly used in the field of pesticide manufacturing. It can be used in the form of a preparation. In actual use, these various formulations can be used directly or diluted with water to a desired concentration. Examples of pesticide auxiliaries mentioned here include diluents (solvents, extenders, carriers), surfactants (solubilizers, emulsifiers, dispersants, wetting agents), stabilizers, fixing agents, and aerosol sprays. agents, etc. Examples of solvents include water: organic solvents; hydrocarbons [e.g., n-hexane, petroleum ether, naphtha,
Petroleum fractions (paraffin wax, kerosene, light oil, middle oil, heavy oil), benzene, toluene, xylenes], halogenated hydrocarbons [e.g., chlormethylene, carbon tetrachloride, trichloroethylene, ethylene chloride, ethylene dibromide, chlorobenzene, chloroform], alcohols [e.g. methyl alcohol, ethyl alcohol, propyl alcohol, ethylene glycol], ethers [e.g. ethyl ether, ethylene oxide, dioxane],
Alcohol ethers [e.g. ethylene glycol monomethyl ether], ketones [e.g. acetone, isophorone], esters [e.g. ethyl acetate, amyl acetate], amides [e.g. dimethylformamide, dimethylacetamide], sulfoxides [e.g. dimethyl Sulfoxide]
etc. can be mentioned. Examples of fillers or carriers include inorganic powders; sulfur, slaked lime, magnesium lime, gypsum, calcium carbonate, silica, perlite, pumice, calcite, diatomaceous earth, amorphous silicon oxide, alumina, zeolite, clay minerals (e.g. pyrofluorite,
Talc, montmorillonite, beidellite, vermiculite, kaolinite, mica): Vegetable granules; Grain flour, starch, modified starch, sugar, glucose, crushed plant stems: Synthetic resin granules; Phenol resin, urea Examples include resin and vinyl chloride resin. Furthermore, examples of surfactants include anionic surfactants; alkyl sulfate esters [e.g. sodium lauryl sulfate], arylsulfonic acids [e.g. alkylaryl sulfonate, sodium alkylnaphthalene sulfonate],
Succinates, polyethylene glycol alkylaryl ether sulfate salts: cationic surfactants; alkylamines [e.g., laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride], polyoxyethylene alkylamines: Nonionic surfactants; polyoxyethylene glycol ethers [e.g.
polyoxyethylene alkylaryl ether,
and their condensates], polyoxyethylene glycol esters [e.g. polyoxyethylene fatty acid esters], polyhydric alcohol esters [e.g. polyoxyethylene sorbitan monolaurate]: amphoteric surfactants, etc. can. Examples of other additives include stabilizers, fixing agents [e.g., agricultural soap, caseinate lime, sodium alginate, polyvinyl alcohol (PVA), vinyl acetate adhesives, acrylic adhesives], aerosol propellants [e.g. , trichlorofluoromethane, dichlorofluoromethane, 1,2,2-trichloro-1,1,2-trifluoroethane, chlorobenzene, LNG, lower ether]: (for smoking agents)
Combustion modifiers [e.g. nitrite, zinc dust, dicyandiamide]: Oxygen supply agents [e.g. chlorate,
Dichromate]: Phytotoxicity reducer [e.g., zinc sulfate,
Ferrous chloride, copper sulfate]: Efficacy extenders: Dispersion stabilizers [eg, casein, tragacanth, carboxymethyl cellulose (CMC), polyvinyl alcohol (PVA)]: and the like. The active ingredient compound used in the present invention can be manufactured into various formulations by methods generally used in the agricultural chemical manufacturing field. Forms of preparations include emulsions, oils, wettable powders, aqueous solutions, suspensions, powders, granules, powders, smoking agents, tablets, aerosols, pastes, capsules, etc. can. The insecticidal composition of the present invention contains an active ingredient compound of about
0.1 to about 95% by weight, preferably about 0.5 to about 90% by weight
It can contain. In actual use, the various formulations and spray preparations described above (ready-to-use)
The content of the active ingredient compound in the preparation is, for example, about 0.0001 to about 20% by weight, preferably about 0.005% by weight.
A range of from about 10% by weight is suitable. The content of these active ingredient compounds can be changed depending on the form of the preparation, the method of application, purpose, timing, location, pest outbreak status, etc. The active ingredient compound used in the present invention may also be used, if necessary, with other agricultural chemicals, such as insecticides, fungicides, acaricides, nematicides, antiviral agents, herbicides, plant length regulators, and attractants. agents, [for example, organophosphate compounds, carbamate compounds, dithio (or thiol) carbamate compounds, organochlorine compounds, dinitro compounds, organosulfur or metal compounds, antibiotics, substituted diphenyl ether compounds, Urea-based compounds, triazine-based compounds]
Or/and fertilizer etc. can also be used together or together. Various formulations or spray preparations (ready-to-use) containing the active ingredient compounds of the present invention.
preparation) refers to the application methods commonly used in the agricultural chemical manufacturing field, such as spraying, spraying, misting,
atomizing, dusting, dusting,
Surface application (e.g., pouring); Smoking; Soil application (e.g., mixing, sprinkling, vaping, irrigating); Surface application (e.g., spreading, banding, dusting,
Coating): Immersion: This can be done by baiting, etc. It can also be used by what is called an ultra-low-volume spraying method. In this way it is possible to have 100% active ingredient content. The application amount per unit area can be, for example, about 0.03 to about 10 kg, preferably about 0.3 to about 6 kg of the active ingredient compound per hectare. However, in special cases it is possible, and sometimes even necessary, to exceed or fall below these ranges. According to the present invention, the active ingredient contains Compound A and one or more organic phosphorous compounds, and further includes a diluent (solvent and/or filler and/or carrier) and/or surfactant, if necessary. In this case, an insecticidal composition containing, for example, a stabilizer and a fixing agent can be provided. Furthermore, according to the present invention, Compound A and one or more of organophosphorus compounds are applied to pests and/or the growing area of the pests alone, or a diluent (solvent and/or filler and/or carrier) and A method for controlling plant pests can be provided in which a mixture of a surfactant and, if necessary, a stabilizer and a fixing agent is applied. EXAMPLES Next, the content of the present invention will be specifically explained with reference to Examples, but the present invention should not be limited thereto. Example 1 (hydrating powder) 15 parts of compound A, 20 parts of trichlorfon, 60 parts of a mixture of powdered diatomaceous earth and powdered clay (1:5), 2 parts of sodium alkylbenzenesulfonate, 3 parts of sodium alkylnaphthalenesulfonate formalin condensate Grind and mix to make a wettable powder. This is diluted with water and sprayed onto pests and/or their growing areas. Example 2 (hydrating powder) 20 parts of compound A, 10 parts of fenthion, 65 parts of a mixture (1:5) of white carbon (hydrated amorphous silicon oxide fine powder) and powdered clay, 2 parts of sodium alkylbenzenesulfonate, alkylnaphthalene Three parts of a sodium sulfonate formalin condensate are ground and mixed to prepare a wettable powder. This is diluted with water and sprayed onto pests and/or their growing areas. Example 3 (Emulsion) 20 parts of Compound A, 20 parts of fenitrothion, 45 parts of dimethylformamide, 8 parts of polyoxyethylene alkyl phenyl ether, and 7 parts of calcium alkylbenzenesulfonate are mixed and stirred to prepare an emulsion. Dilute this with water and remove pests and/or
Spray the areas where they grow. Example 4 (Powder) 1.5 parts of Compound A and 1.5 parts of an organic phosphorus compound are pulverized and mixed with 97 parts of powdered clay to prepare a powder. Sprinkle this on pests and/or their growing areas. As the organic phosphorus compound, fenthion, fenitrothion, diazinon, fentoate, trichlorfon, propafos, tetrachlorvinphos, dimethylvinphos, pyridafenthion, phosmet, chlorpyrifos-methyl, malathion, IBP, and edeifuenphos are used. Example 5 (Powder) 1.5 parts of Compound A, 1.5 parts of edeifuenphos, and 1.5 parts of fenthion are pulverized and mixed with 95.5 parts of powdered clay to prepare a powder. Sprinkle this on pests and/or their growing areas. Example 6 (granules) Compound A 3 parts, diazinon 2 parts, bentonite (montmorillonite), 35 parts, talc (talc)
Add water to a mixture of 58 parts and 2 parts of lignin sulfonate.
Add 25 parts of the mixture, mix well, make 10 to 40 mesh granules using an extrusion granulator, and dry at 40 to 50°C to make granules. Sprinkle this on pests and/or their growth areas. The mixed active compounds according to the invention are characterized by a substantially improved efficacy and by a very low toxicity towards warm-blooded animals, which makes them very useful. The unexpected superiority and remarkable effectiveness of the mixed active compounds of the present invention can be seen from the following test results against various pests. Test example 1 Test against carbamate and organophosphorus agent resistant black leafhopper Test method: Seedlings of rice (variety: Koganenishiki) (2~
2.5-leaf stage, plant height 15-17 cm) were transplanted with 3-5 plants per plant. 45 days after transplanting, 1 plot of 300 m ² in two rows
A predetermined amount of each concentration of powder prepared in the same manner as in Examples 4 and 5 was spread onto a paddy field at 30 kg/ha using a backpack-type power duster and a pipe duster with a length of 30 m. Before spraying, and on the 1st and 5th day after spraying, Nephotettix cincticeps was scooped out by shaking it with an insect net 30 times, anesthetized with ether, and the number of insects was counted after death. The control rate was calculated using the following formula. Control rate (%) = [1 - (number of insects after spraying in treated area / number of insects before spraying in treated area / number of insects after spraying in untreated area / number of insects before spraying in untreated area)] x 10
0 The results are shown in Table 1.

【table】

[Table] Test example 2 Test method for planthoppers: Seedlings of rice (variety: Koganenishiki) (2-
2.5 leaf stage, plant height 15 to 17 cm) were transplanted at a rate of 3 to 5 plants per plant. 45 days after transplanting, 1 plot of 300 m ² in two rows
A predetermined amount of each concentration of powder prepared in the same manner as in Examples 4 and 5 was applied to a paddy field at 30 kg/ha using a backpack-type power duster and a pipe duster with a length of 30 m. Before spraying and on the 1st and 7th day after spraying, the white-legged planthopper (Sogatella furcifera) and brown-throated planthopper (Laodelphax striatellus) were shaken 30 times with an insect net, scooped up, anesthetized with ether, and the total number of brown-legged planthoppers and brown-legged planthoppers was investigated after killing. did. The control rate was calculated using the following formula. Control rate (%) = [1 - (number of insects after spraying in treated area / number of insects before spraying in treated area / number of insects after spraying in untreated area / number of insects before spraying in untreated area)] x 10
0 The results are shown in Table 2.

[Table] Test example 3 Test against resistant peach aphid Eggplant (Group No. 2) was planted in a pot with a diameter of 15 cm.
When the plants were 15 cm tall (6-7 leaf stage), about 100 resistant green peach aphids (Myzus persicae) were inoculated per pot. Two days after inoculation, after counting the number of insects living on the eggplant leaves, a mixed emulsion of each drug prepared according to the method of Example 3 was diluted with water using a spray gun at a pressure of 2 kg/cm ² and spread. An appropriate amount of the drug was added and sprayed in sufficient amount to cause the drug solution to drip. Two days after spraying, the number of dead insects was counted and the killing rate was calculated. The results are shown in Table 3.

【table】

【table】

Claims (1)

[Claims] 1 Dimethyl 4-methylthio-m-tolyl phosphorothioate, S-[α-(ethoxycarbonyl)benzyl]dimethyl phosphorothiolothionate, dimethyl 2,2,2-trichloro-1-hydroxy Ethylphosphonate, S-1,2-bis(ethoxycarbonyl)ethyldimethylphosphorothiorate, S-2-ethylsulfinyl-1-methylethyldimethylphosphorothiolate, Dimethyl S-(N-methylcarbamoylmethyl Phosphorothiorothionate, Ethyl P-nitrophenyl phenylphosphonothionate, S-[2-methoxy-5-oxo-1,3,4
-diazolin-4-ylmethyl] dimethyl phosphorothiorothionate, diethyl 5-phenyl-3-isoxazolyl phosphorothioate, p-cyanophenyl dimethyl phosphorothioate, S-(N-ethoxycarbonyl-N -Methylcarbamoylmethyl)diethylphosphorothiorothionate, 2-Methoxy-4H-1,3,2-benzdioxaphosphorine 2-sulfide, DimethylS-2-(1-methylcarbamoylethylthio)ethylphosphorothio 2-methoxy-4-(2-methoxyphenyl)-1,3,4-oxadiazo A composite insecticide characterized by containing phosphorus-5-one as an active ingredient.