JPH0113445B2 - - Google Patents

Description

[Detailed description of the invention]

3'-phenoxy-α-cyanobenzyl 1-(4
-ethoxyphenyl)-2,2-dichlorocyclopropanecarboxylate (hereinafter referred to as "Compound A")
It is abbreviated as. ) and dl-3-allyl-2-methyl-4-oxo-2-cyclopentenyl dl-cis/
trans-chrysanthemate (hereinafter referred to as "Compound B")
It is abbreviated as. )dl-3-allyl-2-methyl-
4-oxo-2-cyclopentenyl d-cis/trans-chrysanthemate (hereinafter referred to as "Compound C")
It is abbreviated as. ) d-3-allyl-2-methyl-
4-oxo-2-cyclopentenyl d-trans-chrysanthemate (hereinafter abbreviated as "Compound D"), (1,3,4,5,7,6,-hexahydro-1,3-dioxo- 2-isoindolyl)methyl dl-cis/trans-chrysanthemate (hereinafter abbreviated as "Compound E"), (5-
(benzyl-3-furyl)methyl dl-cis/trans-chrysanthemate (hereinafter abbreviated as "Compound F"), (5-benzyl-3-furyl)methyl d-cis/trans-chrysanthemate (hereinafter abbreviated as "Compound F") , abbreviated as "Compound G"), [5-(2-propynyl)-2-furyl]methyl dl-cis/trans-chrysanthemate (hereinafter abbreviated as "Compound H"), [5- (2-propynyl)-2-furyl]methyl d-cis/trans-chrysanthemate (hereinafter abbreviated as "Compound I"), 3-
Phenoxybenzyl dl-cis/trans-3-
(2,2-dichlorovinyl)-2,2-dimethyl-
1-cyclopropanecarboxylate (hereinafter referred to as
It will be abbreviated as "Compound K". ), [1R−[1α(S ^* ),
3β]-2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl 2,2
-dimethyl-3-(2-methyl-1-propenyl)
Cyclopropane carboxylate (hereinafter abbreviated as "Compound L") and 5-benzyl-3-
Furylmethyl (1R, cis(E))-2,2-dimethyl-3-(2'-oxo-3'-thiocyclopentylidenemethyl)-1-cyclopropanecarboxylate (hereinafter abbreviated as "Compound M") This invention relates to an insecticidal composition containing as an active ingredient at least one compound selected from the group consisting of: Today, as a result of repeated spraying of chemicals for the purpose of controlling various pests such as sanitary pests, forest pests, pasture pests, and agricultural and horticultural pests, strains of each pest with reduced chemical susceptibility have appeared in various places, and control techniques and This has become a major problem in farm management. Therefore, it shows remarkable insecticidal efficacy, fast-acting insecticidal efficacy, and long-term sustained efficacy against these insect pests, especially strains with reduced drug susceptibility, and reduces the number of times and dosage of chemical spraying. However, there is a strong desire for a pest control agent that is highly safe for humans and livestock and causes less environmental pollution. As a result of intensive research, the present inventors have found that a composition containing at least one compound selected from the group consisting of Compound A and Compounds B to P as an active ingredient is effective against sanitary pests, other forest pests, and pasture pests. Or, as a result of further research based on the discovery that it has a reliable control effect against agricultural and horticultural pests, etc.
completed this invention. The insecticidal composition of the present invention has a surprising control effect that cannot be estimated from the efficacy of each single agent in terms of insecticidal efficacy, rapid fall-off efficacy, flushing efficacy, insecticidal efficacy, and sustained insecticidal efficacy against drug-resistant pests, i.e. The characteristic properties of single agents are not merely additive, but exhibit a remarkable synergistic effect. As a result, the range of uses has been expanded, more reliable control effects have been obtained, the number of times the chemical has been sprayed has been reduced, and the amount of spraying has been approximately 1/1/1 of the amount normally sprayed with each single agent.
It can be reduced by 2 to 1/3, ensuring safety for humans and animals and reducing environmental pollution. In addition to the house fly, German cockroach, etc., pests to which the composition of the present invention can be applied are the Japanese cockroach, the brown borer moth, the Japanese white cockroach, the Japanese cockroach, the black cockroach, the American cockroach, the Culex pipiens, the Culex pipiens, the Aedes aegypti mosquito, the black weevil, the Japanese white borer, the Japanese white borer moth, and the Japanese azuki bean. Weevils, black leafhoppers, white planthoppers, brown planthoppers, brown planthoppers, snowy green aphids, white snails, black-bellied flycatchers, small-breasted beetles, red-spotted beetles, burrs, aedes albopictus, rice fall armyworms, cotton aphids, black flies, midges, midges, yellow-throated beetles, two-legged spider mites, two-legged flycatchers moth, cypress moth, rice leafminer fly, Rice leafminer fly, rice carabfly, rice leaf beetle, rice water weevil, rice weevil, diamondback moth, armyworm, fall armyworm,
Japanese white flycatcher, Japanese corn borer moth, Japanese bean moth, white-spotted moth, Japanese white bean moth, green peach aphid, false radish aphid, orange black aphid, rosemary aphid, whitefly, American white flycatcher, gypsy moth, pine currant moth, short-tailed white moth, peach moth, Japanese white moth , Citrus leafminer moth, Chinese yellow thrips, Korean leafminer, Gomadara leafminer,
It can also be applied to various pests such as the snail moth and the striped armyworm. When using the above-mentioned composition of the present invention, depending on the purpose of use, it may be used as it is by diluting it directly with water, or it may be used as a sanitary pest control agent, a forest pest control agent, a pasture pest control agent, or an agricultural and horticultural pest control agent. Emulsions, wettable powders, powders, granules, oils, aerosols, flowables, microcapsules, and high-density powders are prepared by using auxiliary agents for pest control agents and by methods commonly used in the field of formulations such as sanitary pest control agents. It can be used in the form of a formulation such as a small concentration spray. In actual use, these various preparations can be used directly or diluted with water to a desired concentration. The adjuvants referred to here include inert solvents and/or solid diluents, as well as various surfactants and/or solid diluents.
Alternatively, organic raw materials can be mentioned. Insoluble solvents include petroleum fractions such as kerosene and light oil, aromatic hydrocarbons such as toluene and xylene, alcohols such as methylnaphthalene, cyclohexane, methanol, butanol, and glycol, amides such as acetone and dimethylformamide, and dimethyl sulfoxide. Examples include sulfoxides such as, animal and vegetable oils, fatty acid esters, etc. Examples of solid diluents include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, and the like. Examples of the surfactant include anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkyl phenyl ether, lauryl betaine, cationic surfactants, nonionic surfactants, Examples include zwitterionic surfactants. In addition to the above-mentioned auxiliary agents, auxiliary agents such as spreading agents, emulsifiers, wetting agents, dispersants, fixing agents, and disintegrants can be appropriately mixed as necessary to ensure the insecticidal effect. In the insecticidal composition of the present invention, the concentration of the mixture of Compound A and other active ingredients in the formulation is 0.005 to 95%.
(by weight), preferably 0.01 to 50% (by weight), more preferably 0.1 to 10% (by weight). The blending ratio of compound A and other active ingredients is
Other active ingredients for 1 part by weight of compound A
It can be contained in a range of 0.005 to 5.0 parts by weight, preferably 0.01 to 3.0 parts by weight, more preferably 0.02 to 2.0 parts by weight. The amount of the composition of the present invention to be used varies depending on the dosage form, method of application, timing, and other conditions, but for sanitary pest control agents, this agent is usually used at an amount of ² active ingredients per 1 m2.
~200mg, preferably 5 to 100mg is used, and in agricultural and horticultural pest control agents, forest pest control agents, and pasture pest control agents, this agent is usually used at an amount of 20 mg of active ingredient per 10 ares.
~300g, preferably 30-200g is used. For example, powders contain 30 to 120 g of active ingredient per 10 ares.
Powders have an active ingredient content of 120 to 240 g, and emulsions and wettable powders have an active ingredient content of 40 to 250 g. However, in special cases it is possible, and sometimes even necessary, to exceed or fall below these ranges. All formulations can be used alone, or mixed with fungicides, herbicides, plant growth regulators, agricultural and horticultural fungicides, soil fungicides, soil improvers, nematicides, or acaricides. It can also be mixed with fertilizers and other pesticides. Next, formulation examples of the present invention will be explained in more detail in the following examples, but the types and mixing ratios of additives are not limited to these and can be used in a wide range. Note that "part" means "weight part"
means. Example 1 Emulsion 10 parts of compound A and 3-phenoxybenzyl dl-cis/trans-3-(2,2-dichlorovinyl)-
55 parts of a xylene-methylnaphthalene mixture (1:1) was added to 20 parts of 2,2-dimel-1-cyclopropanecarboxylate (compound K) and dissolved, and then alkylphenol oxide ethylene condensate and alkylbenzene sulfone were added to the solution. Add 15 parts of a calcium acid mixture (8:2) to form an emulsion. This agent is diluted 1000 to 3000 times with water and used as a spray solution. Note that emulsions can be obtained in the same manner for compounds A to M other than compound K. Example 2 Wettable powder 10 parts of compound A and dl-3-allyl-2-methyl-
10 parts of 4-oxo-2-cyclopentenyl d-cis/trans-chrysanthemate (compound C) was mixed with 72.5 parts of synthetic fine silicic acid powder, and a mixture of sodium laurate and sodium dinaphthyl methanesulfonate (1: 1) Mix 7.5 parts and pulverize to obtain a powder. This agent is diluted 1,000 to 4,000 times with water and used as a spray liquid as a hydrating agent. Example 3 Powder 1 part of compound A and (5-benzyl-3-furyl)
Add 95 parts of a mixture of talc and calcium carbonate (1:1) to 2 parts of methyl dl-cis/trans-chrysanthemate (compound F), mix and grind to thoroughly disperse and blend, and then add a small amount of synthetic silicic acid. Add 2 parts of powder and mix and crush to make a powder. This agent can be used as is by spraying. Example 4 Powder 2.5 parts of compound A and (1,3,4,5,6,7-
2.5 parts of hexahydro-1,3-dioxo-2-isoindolyl)methyl dl-cis/trans-chrysanthemate (compound E) was added to fine bentonite powder.
After mixing with 47 parts of talc, 46 parts of talc, and 2 parts of sodium ligninsulfonate, water is added and kneaded until uniform. Next, the mixture is granulated using an injection molding machine, and then passed through a sieve, a dryer, and a sieve to form granules with a particle size of 0.6 to 1.0 mm. This agent is used by directly scattering it on the paddy field and soil surface. Example 5 Oil agent 0.125 parts of compound A and dl-3-allyl-2-methyl-4-oxo-2-cyclopentenyl dl-cis/trans-chrysanthemate (compound B)
An oil agent is obtained by mixing and dissolving 99.5 parts of xylene in 0.375 parts. This agent can be directly sprayed or applied. Example 6 Aerosol agent 0.2 parts of compound A and 5-benzyl-3-furylmethyl (1R, cis(E))-2,2-dimethyl-3-
0.5 parts of (2'-oxo-3'-thiocyclopentylidenemethyl)-1-cyclopropanecarboxylate (compound M) was dissolved in 49.7 parts of a mixture of methylnaphthalene and cyclohexane (1:1), and further 50 parts of freon. An aerosol can be obtained by mixing the mixture into a homogeneous solution and processing it into an aerosol form. This agent can be used as is by spraying. As is clear from various experimental examples as described below, the insecticidal composition of the present invention has superior drug-resistant pest insecticidal efficacy, fast-acting supine fall efficacy, flushing efficacy, and insecticidal efficacy as compared to each single agent. It shows sustained insecticidal efficacy and also shows excellent control effect in model tests (semi-field). Experimental example 1 House fly adult insecticidal test (according to the Nagasawa spray drop test method) Emerging into a glass pot (B) with a diameter of 13 cm and a height of 15 cm 2
After ~4 days, 20 adult female houseflies resistant to phosphorus were released and covered with 16 meshes of gold thread. diameter 20
0.5 ml of an acetone diluted solution of each specimen was sprayed from a glass spray nozzle at a pressure of 1.0 to 1.5 Kg/cm ³ through the upper hole of a glass cylinder (A) measuring cm×height 42 cm. After 10 seconds A.
B Remove the glass plate placed between both glass cylinders,
The spray was allowed to come into contact with adult house flies. 1
The test was carried out in two consecutive sections, and the number of insects turning upside down was investigated at predetermined intervals after the glass plate was removed. The supine insect rate obtained from this was plotted on logarithmic probability paper, and the 50% supine turning time (KT-50) was determined. The results are shown in Table 1.

【table】

[Table] Experimental example 2 House fly adult insecticidal test Each emulsion was diluted with well water to the specified concentration and 1 m ² of the chemical solution was used.
50 ml per volume was added uniformly onto Toyoro paper No. 2 using a measuring pipette. After air-drying, a glass shear with a diameter of 9 cm and a height of 2 cm containing 20 adult female house flies, 2 to 4 days after emergence, was placed on the same paper and brought into contact with the chemical. The number of insects turning upside down at predetermined intervals after contact with the drug and the number of dead insects 24 hours later were investigated. The test was carried out in two consecutive sessions in each section, and the rate of insects turning over at each specified time was plotted on log probability paper.
The 50% supine rotation time (KT-50) was determined. Similarly, sustained insecticidal efficacy was examined 3 and 15 days after treatment. The results are shown in Table 2.

[Table] Experimental example 3 House fly adult insecticidal test 50 female house fly adults 2-4 days after emergence were released into a semi-field device (width 1 m x 0.9 m x height 2 m), and 2 ml of each oil solution was applied at a pressure of 1.0 to 1.5 kg. /m ² with a glass spray nozzle. The number of insects turning upside down was investigated at predetermined intervals after spraying. Furthermore, 30 minutes after spraying, supine insects were placed in a 200 ml ice cream cup, and the number of dead insects and whether or not they had been resuscitated were examined 24 hours later. Ward 1 3
It was carried out in tandem. The results are shown in Table 3.

[Table] Experimental Example 4 German Cockroach Adult Insect Killing Test Each emulsion was diluted with well water to a predetermined concentration, and 50 ml of the chemical solution was uniformly dropped onto ^each square meter of plywood using a measuring pipette. After air-drying, the container was covered with a glass jar measuring 9 cm in diameter and 6 cm in height, and 10 adult male German cockroaches were released inside, and the number of dead insects was counted 24 hours later. The sustained insecticidal efficacy was investigated using the same method on the 10th and 30th day after chemical treatment. It was conducted in two consecutive sessions in each ward. The results are shown in Table 4.

[Table] Experimental example 5 German cockroach adult insecticidal test 10×10 in a glass pot with a diameter of 21 cm and a height of 11 cm.
A shelter made of 3 cm-sized plywood boards stacked 1 cm apart was placed, and 10 male and female German cockroaches were released into the shelter. After the cockroaches are stationary inside the shelter, a semi-field device (width 1m x width 0.9m x
The pot was placed on a small table (height 60 cm) in a glass pot (height 2 m), and 1 ml of each oil agent was sprayed from a glass spray nozzle at a pressure of 1.0 to 1.5 kg/cm ² from 60 cm directly above the glass pot. After spraying, the number of insects flying out from the shelter (flushing effect) and the number of turning insects were measured over time, and
Thirty minutes after spraying, all the German cockroaches were placed in ice cream cups, and the number of dead insects was counted 24 hours later. In addition, the glass pots and shelters in which the cockroaches were collected were again released with male and female adult German cockroaches on the 20th day after spraying, and the number of dead insects was investigated 24 hours later. It was carried out in three consecutive districts. 50% flying insect rate (FT-50) and 50 for each specified time
The % supine insect rate (KT-50) was determined by plotting on log probability paper. The results are shown in Table 5.

【table】

Claims (1)

[Claims] 1 3'-phenoxy-α-cyanobenzyl 1-
(4-ethoxyphenyl)-2,2-dichlorocyclopropanecarboxylate and dl-3-allyl-2-methyl-4-oxo-2-cyclopentenyl-dl-cis/trans-chrysanthemate,
dl-3-allyl-2-methyl-4-oxo-2-
Cyclopentenyl d-cis/trans-chrysanthemate, d-3-allyl-2-methyl-4-
Oxo-2-cyclopentenyl d-trans-chrysanthemate, (1,3,4,5,6,7-
Hexahydro-1,3-dioxo-2-isoindolylmethyl dl-cis/trans-chrysanthemate, (5-benzyl-3-furyl)methyl dl
-cis/trans-chrysanthemate, (5benzyl-3-furyl)methyl d-cis/trans-chrysanthemate, [5-(2-propynyl)
-2-furyl]methyl dl-cis/trans-chrysanthemate, [5-(2-propynyl)-2-
furyl] methyl d-cis/trans-chrysanthemate, 3-phenoxybenzyl dl-cis/trans-3-(2,2-dichlorovinyl)-2,2
-dimethyl-1-cyclopropanecarboxylate, [1R-[1α(S ^* ),3β]]-2-methyl-4
-oxo-3-(2-propenyl)-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-
Methyl-1-propenyl)cyclopropanecarboxylate and 5-benzyl-3-furylmethyl (1R, cis(E))-2,2-dimethyl-3-
An insecticidal composition containing as an active ingredient at least one compound selected from the group consisting of (2'-oxo-3'-thiocyclopentylidenemethyl)-1-cyclopropanecarboxylate. thing.