JPH0432043B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula (In the formula, X represents a methyl group, a chloro atom, or a bromo atom, and R represents a hydrogen atom or a cyano group.) and 2-isopropylphenyl-N- The present invention relates to an insecticide for heat fumigation characterized by containing methyl carbamate as an active ingredient in a composition ratio of 9 to 2:1 to 8. Pyrethroid compounds represented by the general formula () exhibit extremely excellent insecticidal effects against various sanitary pests and agricultural and horticultural pests, while their toxicity to warm-blooded animals is low, and they have already been used as household, epidemic prevention, and agricultural insecticides. It is widely used in practical applications. Until now, it has been considered difficult to develop resistance to these pyrethroids, and in fact, there have been no problems in terms of control in Japan, but houseflies in Northern Europe and diamondback moths in Southeast Asia have pyrethroid resistance. Considering the emergence of new strains and the tenacity shown by living organisms to ensure the survival of their species, it is considered appropriate to take measures based on the possibility of resistance development in Japan as well.
Moreover, the development of these pyrethroid resistances is not dependent on the metabolic system, but involves a mechanism based on decreased neurosensitivity, and as a result, the phenomenon of pyrethroid cross-resistance has appeared, and as a solution to this phenomenon, organophosphate It has become important to develop applications including the mixed use of pyrethroids and drugs with different physiological effects, such as carbamate agents. Therefore, the present inventors
We started this research by focusing on carbamate agents rather than organic phosphorus agents, which have many problems in terms of stability and toxicity. Incidentally, alkyl-substituted phenyl-N-methylcarbamates are widely used as insecticides against agricultural pests, but are mostly limited to spraying, and mixtures with pyrethroids in spraying insecticides do not necessarily have a synergistic effect. It wasn't satisfying. Therefore, the present inventors attempted to apply an alkyl-substituted phenyl-N-methyl carbamate agent to fumigation, and further investigated a mixture with a pyrethroid agent. As a result, among the various alkyl-substituted phenyl-N-methyl carbamates, especially 2
A mixture of -isopropylphenyl-N-methyl carbamate and a pyrethroid of the general formula () is
We have completed the present invention by discovering that when used for heat fumigation, it is extremely superior not only in its synergistic effect but also in terms of volatilization rate and resistance measures. That is, the combination of 2-isopropylphenyl-N-methyl carbamate and pyrethroid is
Specifically, the discovery that it more than complements the traditional efficacy of carbamates' lethality and pyrethroids' fast-acting properties, and is extremely effective against resistant insect pests, is a major challenge for traditional spray insecticides. This is completely unpredictable in terms of effectiveness. The pyrethroid of general formula () used as an active ingredient in the present invention is known and is solid or liquid at room temperature. Typical examples thereof are as follows, but the present invention is not limited thereto. In addition, all pyrethroids have two inhospitable carbons in the acid moiety, and if R is a cyano group, one in addition, and there are optical isomers based on these, but each isomer or Naturally, mixtures thereof are also included in the present invention. (1) 3'-Phenoxybenzyl chrysanthemate (2) 3'-Phenoxy-α'-cyanobenzyl chrysanthemate (3) 3'-Phenoxybenzyl 2,2-dimethyl-3-(2,2- dichlorovinyl) dichloropropane carboxylate (4) 3'-phenoxy-α'-cyanobenzyl 2,
2-dimethyl-3-(2,2-dichlorovinyl)
Cyclopropanecarboxylate (5) 3'-phenoxy-α'-cyanobenzyl 2,
2-dimethyl-3-(2,2-dibromovinyl)
Cyclopropanecarboxylate On the other hand, 2-isopropylphenyl-N-methylcarbamate used in the present invention is solid at room temperature (m.
p.89-91°C), and can be easily produced by reacting 2-isopropylphenyl with methyl isocyanate or methylcarbamic acid chloride according to the general method for producing carbamates. When using this as an insecticide for heat fumigation,
The above pyrethroid and carbamate in a ratio of 9 to 2:1
A mixture containing a composition ratio of ~8 can be used as it is or after being made into a solution with a suitable solvent, mixed with wood flour or other suitable base material and used as a dosage form such as a mosquito coil. Furthermore, there is a method of mixing the active ingredient with a combustion agent and using it as a so-called smoking agent in which the chemical is released by the combustion heat and smoke of the combustion agent, and a method of mixing the active ingredient with an organic foaming agent and encapsulating it,
It is also possible to heat the mixture indirectly to thermally decompose the organic blowing agent without combustion, and to effectively fumigate the agent by the action of the thermally decomposed gas.
Further, as a heating fumigant, the active ingredient solution can be applied to a form such as an electric mosquito repellent described later. In addition, the above composition contains N-octylbicycloheptenedicarboximide (trade name).
MGK-264), mixture of N-octylbicycloheptenedicarboximide and arylsulfonate (trade name MGK-5026), octachlorodipropyl ether, piperonyl butoxide, cinepirin 500, β-butoxy-β- Addition of a pyrethroid synergist such as thiocyanodiethyl ether (trade name Riesen 384) or Sesamex can further enhance its insecticidal efficacy. Furthermore, BHT
Adding antioxidants such as DBHQ, BHA, and Yoshinox 425 is effective in improving stability. Also other active ingredients such as fenitrothion,
Organic phosphorus agents such as DDVP, diazinon, propaphos, and pyridafenethione, carbamate agents such as Sevin, Meovar, and Sancide, insecticides such as Cartap, chlorphenamidine, and methomyl, acaricides, fungicides, and green insecticides. A highly effective multipurpose composition can also be obtained by mixing pesticides, herbicides, plant growth regulators, fertilizers and other agricultural chemicals. The composition of the present invention can be used not only for susceptible pests, but also for organic phosphorus agent-, carbamate-resistant, or KDR-based pests such as flies, mosquitoes, cockroaches, and other sanitary pests, as well as leafhoppers, planthoppers, stinkbugs, and stink bugs. It is extremely useful for controlling agricultural pests such as leafhoppers, aphids, scale insects, armyworms, bean weevils, etc., husk pests such as black elephants, and mites. Next, the results of an insecticidal test when the above composition was used as an insecticide for heat fumigation will be shown. (1) 3′-phenoxy-α′-cyanobenzyl chrysansemate (compound (A)) as an insecticidal ingredient: 0.15
% and mosquito coil containing 0.15% of 2-isopropylphenyl-N-methyl carbamate (compound (B)) and 0.3% of compound (A) as a control, respectively.
Compound (B) 0.3%, compound (A) 0.15% and 2-ethylphenyl-N-methylcarbamate (compound
(C)) 0.15%, compound (C) 0.3%, allethrin 0.3%
We made six types of mosquito coils, including the following, and tested their effectiveness in making adult Culex mosquitoes fall and turn upside down. This experiment was conducted using the method of Nagasawa, Katsuta, et al. described in "Insect Control Science", Vol. 16 (1951), p. 176, and the relative effectiveness of the above incense sticks was calculated using this method. However, the following results were obtained. Furthermore, the volatilization rate of the active ingredient was also measured for each incense stick.

[Table] As a result of the test, the carbamate agent of compound (B)
When used as a fumigant, it exhibits greater efficacy than allethrin, which is generally in practical use, and when mixed with compound (A), it exhibits a remarkable synergistic effect that is not observed with other carbamates, such as compound (C). Ta. (2) 3′-phenoxybenzyl d as an insecticidal ingredient
-cis,trans-chrysanthemate (trade name: Sumitrin, compound (D)) and 2-isopropylphenyl-N-methylcarbamate (compound (B))
and mixing of compound (D) and 3-methylphenyl-N
- Mix methyl carbamate (compound (E)) and acetone solution of allethrin in a 30 mm x 60
Adsorb it onto a mm x 1.5 mm pulp board and air dry. This pulp board was placed on a heating element at 160°C, and an electric mosquito repellent method was used to heat and evaporate, and an effectiveness test was conducted using adult house flies. i.e. ^25m3
In a room, a stainless steel cage in which 30 house flies were released was hung at a height of 50 cm from the ceiling, and the relative effectiveness of the drug was calculated from the number of adult house flies that fell and turned upside down after 4 hours of exposure. When I looked into the ratio, it was as follows. As test house flies, we used both susceptible and kdr strains that had been selected over many generations at the laboratory level.

[Table] As a result of the test, the compositions of the present invention (Samples 2 to 5) showed a remarkable synergistic effect against susceptible house flies, while they were not effective against conventional pyrethroid single agents or other carbamate agents against KDR house flies. It was found to be extremely effective compared to the mixture of (3) 3′-Phenoxybenzyl as an insecticidal ingredient
Contains a predetermined amount of 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate (permethrin, compound (F)) and 2-isopropylphenyl-N-methylcarbamate (compound (B)). A fumigation agent was prepared and tested against cotton aphids in a greenhouse using the following method. Cultivation required Kiyuuri variety Kurume H type Plant height at test 1.3 to 1.5 m Distinction, area House capacity 400 m ³ Survey date and method Divide the house into 9 equal parts and height 1.0 to 1.5 m
One location and one leaf of M were selected and the number of parasitic cotton aphids was investigated. The number of surviving insects was investigated 24 hours after fumigation.

【table】

[Table] Examples of the present invention are shown below. Example 1 0.15 g of 3'-phenoxy-α'-cyanobenzyl chrysanthemate and 2-isopropylphenyl-
A mosquito coil containing 0.3% of the active ingredient was prepared by uniformly mixing 0.15 g of N-methyl carbamate with 99.7 g of a base material for mosquito coils such as pyrethrum extract powder, wood flour, and starch. Obtain an incense stick. Example 2 3'-phenoxybenzyl 2,2-dimethyl-
0.12 g of 3-(2,2-dibromovinyl)cyclopropanecarboxylate, 0.20 g of 2-isopropylphenyl-N-methylcarbamate, and 1.0 g of β-butoxy-β'-thiocyanodiethyl ether were mixed with pyrethrum extract powder, wood A mosquito coil was prepared by a conventional method by uniformly mixing with 98.7 g of a base material for a mosquito coil such as powder or starch. Example 3 3'-phenoxybenzyl d-cis, trans-chrysansemate 7g, 2-isopropylphenyl-N-methylcarbamate 3g, DBHQ10
g, add aceone to 10 g of piperonyl butoxide to make 100 ml. Spread 1ml of this insecticidal solution into 30mm x 60mm
The pulp soaked into a mm x 1.5 mm pulp board is placed on an electric heating element and heated to approximately 160°C to evaporate. Example 4 3'-phenoxybenzyl 2,2-dimethyl-3
-(2,2-dichlorovinyl)cyclopropanecarboxylate 20g, 2-isopropylphenyl-N-methylcarbamate 20g, chestnut flour 25g, raw ash 7g, wood flour 11g, diatomaceous earth 11g and manganese dioxide 1.5g uniformly Mix this with potassium chlorate 4.5
Add an aqueous solution prepared by adding 100 ml of water to g, knead well, form into a cylindrical shape, and dry to obtain a heated fumigant. Example 5 (S)-3'-phenoxy-α'-cyanobenzyl d-cis-2,2-dimethyl-3-(2,2-
dibromovinyl) cyclopropane carboxylate (decamethrin) 5g, 3'-phenoxy-α'-
Cyanobenzyl 2,2-dimethyl-3-(2,
2-dichlorovinyl)cyclopropanecarboxylate 5g, 2-isopropylphenyl-N-methylcarbamate 15g, azodicarboxylic acid amide
Add 70g and 5g of CMC, mix uniformly, and form into granules to obtain a heated fumigant.

Claims (1)

[Claims] 1. General formula (In the formula, X represents a methyl group, a chloro atom, or a bromo atom, and R represents a hydrogen atom or a cyano group.)
A heat fumigation product containing as active ingredients one or two of the pyrethroid compounds represented by: and 2-isopropylphenyl-N-methyl carbamate in a composition ratio of 9 to 2:1 to 8. Insecticide.