JP2004285054A - Harmful arthropod-controlling agent - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain an excellent harmful arthropod-controlling agent and to provide a method for controlling the harmful arthropodes. <P>SOLUTION: The harmful arthropod-controlling agent contains an oxadiazine compound expressed by formula (A) [hereinafter described as the compound (A)] and an ester compound expressed by formula (B) as active ingredients. The method for controlling the harmful arthropodes is provided by using effective amounts of the oxadiazine compound expressed by formula (A) and the ester compound expressed by formula (B) over the harmful arthropodes or at living places of the harmful arthropodes. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to an arthropod pest control agent and a method for controlling arthropod pests.

で示されるオキサジアジン化合物が有害節足動物防除活性を有することが知られている（例えば、特許文献１参照）。
また、式（Ｂ）

で示されるエステル化合物が有害節足動物防除活性を有することも知られている（例えば、特許文献２参照）。 Formula (A)

It is known that the oxadiazine compound represented by the formula (1) has a harmful arthropod control activity (for example, see Patent Document 1).
Equation (B)

It is also known that the ester compound represented by has a harmful arthropod control activity (for example, see Patent Document 2).

Japanese Patent Publication No. 6-504777 JP-A-54-9269

  However, since the arthropod pest control activity of these compounds may not always be sufficient, development of a more excellent arthropod pest control agent is desired.

  The present inventors have conducted intensive studies under such circumstances, and as a result, a harmful arthropod controlling agent containing, as active ingredients, an oxadiazine compound represented by the formula (A) and an ester compound represented by the formula (B), It has been found that when the compound is used alone, it is possible to effectively control pest species having an insufficient control effect, and furthermore, it is possible to reduce the amount of each treatment drug by exerting a synergistic synergistic effect. completed.

で示されるオキサジアジン化合物（以下、化合物（Ａ）と記す。）と、式（Ｂ）

で示されるエステル化合物とを有効成分として含有することを特徴とする有害節足動物防除剤、及び式（Ａ）で示されるオキサジアジン化合物と、式（Ｂ）で示されるエステル化合物との有効量を有害節足動物又は有害節足動物の生息場所に施用することを特徴とする有害節足動物の防除方法を提供する。 That is, the present invention relates to formula (A)

(Hereinafter referred to as compound (A)) represented by the formula (B):

And an oxadiazine compound represented by the formula (A), and an effective amount of the ester compound represented by the formula (B), which comprises an ester compound represented by the formula (B): A method for controlling arthropod pests, which is applied to arthropod pests or habitats of arthropod pests.

  The arthropod pest control agent of the present invention has an excellent arthropod pest control effect.

  The arthropod pest control agent of the present invention is characterized by containing an oxadiazine compound represented by the formula (A) and an ester compound represented by the formula (B) as active ingredients.

The compound represented by the formula (A) constituting the harmful arthropod controlling agent of the present invention (methyl 7-chloro-2,5-dihydro-2-[[(methoxycarbonyl) [4- (trifluoromethoxy) phenyl]] Amino] carbonyl] indeno [1,2-e] [1,3,4] oxadiazine-4a (3H) carboxylate) is a compound described in JP-A-6-504777, which is described in the publication. It can be manufactured according to a given method. Also, (S) -methyl 7-chloro-2,5-dihydro-2-[[(methoxycarbonyl) [4- (trifluoromethoxy) phenyl] amino] carbonyl] indeno [1,2-e] [1, [3,4] oxadiazine-4a (3H) carboxylate has the generic name of indoxacarb. I. Provided by DuPont. Furthermore, (RS) -methyl 7-chloro-2,5-dihydro-2-[[(methoxycarbonyl) [4- (trifluoromethoxy) phenyl] amino] carbonyl] indeno [1,2-e] [1, A flowable preparation of [3,4] oxadiazine-4a (3H) carboxylate (indoxacarb MP) is provided by Kumiai Chemical Industry Co., Ltd. under the trade name “Tornado 10FL”.
The absolute configuration of the asymmetric carbon present in the compound represented by the formula (A) is preferably an S configuration from the viewpoint of the harmful arthropod composition controlling effect. That is, among the compounds represented by the formula (A), S-forms or those rich in S-forms are preferably used.

  Further, the compound represented by the formula (B), which constitutes the arthropod pest control agent of the present invention, is a compound described in JP-A-54-9269, and is produced according to the method described therein. be able to.

Examples of the arthropod pests to which the arthropod pest control agent of the present invention exhibits a controlling effect include, for example, pests and pests, specifically, for example, the following.
Hemiptera: Insects such as the brown planthopper (Laodelphax striatellus), the brown planthopper (Nilaparvata lugens), the brown planthopper (Sogatella furcifera), the leafhopper (Nephotettix cincticeps), the leafhopper (Nephotettix aphi), choppers, etc. , Aphid such as peach aphid (Myzus persicae), stink bugs such as Nezara antennata, Riptortus clavetus, sting bugs such as Trialeurodes vaporariorum, and Bemisia argentoli such as silver leaf whitefly (Trialeurodes vaporariorum) , Mosquitoes such as Aonidiella aurantii, Arnidiella aurantii, San Jose scale insects (Comstockaspis perniciosa), citrus snow scale (Unaspis citri), ruby beetle (Ceroplastes rubens), Icerya purchasi Grasshoppers, hornworms, lice, etc.

Lepidoptera: Pests such as Chilo suppressalis, Cnaphalocrocis medinalis, Notarcha derogata, and Plodia interpunctella, Spodoptera litura, Pseudosia, parataia, and Pseudaia sp. Noctuids such as Heliotis, Helicoverpa, etc., white butterflies such as Pieris rapae, Adoxophyes spp. Genus Lepidoptera, Limantria, Euproctis, etc., Scutellaria such as Plutella xylostella,
Kibaga such as cotton beetle (Pectinophora gossypiella), Triggers such as Hyphantria cunea, and Hirozkoga such as Iga (Tinea translucens) and Koiga (Tineola bisselliella).

  Diptera: Pests such as Culex pipiens pallens, Culex tritaeniorhynchus, Culex quinquefasciatus, Culex quinquefasciatus, Aedes aegypti; House flies such as anopheles, midges, houseflies (Musca domestica) and house flies (Muscina stabulans); , Drosophila, Drosophila, Blackflies, Tabby, Dermatophagoids, Lepidoptera, etc.

  Coleoptera: Pests such as corn rootworms such as Western corn worm (Diabrotica virgifera virgifera) and Southern corn root worm (Diabrotica undecimpunctata howardi); Weevils such as Sitophilus zeamais, rice weevil (Lissorhoptrus oryzophilus) and azuki weevil (Callosobruchuys chienensis), tenebrio molitor; striolata), leaf beetles such as colorado potato beetle (Leptinotarsa decemlineata), etc., epilacunas such as Epilachna vigintioctopunctata, etc., leaf beetles, etc. Shi acids, Cerambycidae such, Aoba ants backlash Staphylinidae (Paederus fuscipes), and the like.

Cockroach pests: German cockroaches (Blattella germanica), black cockroaches (Periplaneta fuliginosa), brown cockroaches (Periplaneta americana), brown cockroaches (Periplaneta brunnea), black cockroaches (Blatta orientalis) and the like.
Thripidae pests: Thrips palmi (Thrips palmi), Thrips tabaci (Thrips tabaci) and the like.

Hymenopteran pests: Ants such as ants, hornets, wasps, and wasps such as Japanese wasps (Athalia japonica).
Orthoptera pests: Kera, grasshoppers and the like.
Laminariae pests: cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis), human flea (Pulex irritans), keops murine flea (Xenopsylla cheopis) and the like.
Louse pests: white lice (Pediculus humanus corporis), lice (Phthirus pubis), bovine lice (Haematopinus eurysternus), sheep lice (Dalmalinia ovis) and the like.
Termite pests: Yamato termites (Reticulitermes speratus), house termites (Coptotermes formosanus) and the like.

  Acarid pests: Tetranychus urticae, red mites (Panonychus citri), spider mites such as Oligonicus spp. Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus, Boophilus microplusne, etc. , Dermatophagoides farinae (Dermatophagoides farinae), Dermatophagoides pternyssnus (Dermatophagoides ptrenyssnus), Dermatophagoid mites (Tyrophagus putrescentiae), Dermatophagoid mites (Cheyletus eruditus) ensis) and mites (Cheyletus moorei), mites and mites.

  In the arthropod pest control agent of the present invention, the weight ratio of the oxadiazine compound represented by the formula (A) to the ester compound represented by the formula (B) is usually 50: 1 to 1:10, preferably 20: 1 to 1: 4.

  The arthropod pest control agent of the present invention may be a mixture itself of the oxadiazine compound represented by the formula (A) and the ester compound represented by the formula (B), but is usually further a solid carrier and a liquid carrier. , And / or a gaseous carrier and the like, and if necessary, a surfactant and other pharmaceutical auxiliaries are added, and emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, pastes are prepared. It is formulated into preparations, foams, aerosols, carbon dioxide preparations, sheet preparations, resin preparations, smokers, poison baits and the like.

  These preparations usually contain 0.005 to 90% by weight in total of the oxadiazine compound represented by the formula (A) and the ester compound represented by the formula (B).

  Examples of the solid carrier used in the formulation include clays (kaolin clay, diatomaceous earth, bentonite, fubasami clay, acid clay, etc.), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur) , Activated carbon, calcium carbonate, hydrated silica, etc.) and fine powders and granules of chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, salt ammonium, etc.).

  Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (E.g., toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate) Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyro) Ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc.) ), Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), propylene carbonate and vegetable oil (Soy oil, cottonseed oil, etc.).

  Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

  Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyethylene glycol fatty acid esters, and the like, and salts such as alkyl sulfonates, alkyl benzene sulfonates, and alkyl sulfates. Ionic surfactants.

  Other adjuvants for pharmaceuticals include fixing agents, dispersants, coloring agents and stabilizers, specifically, casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymer (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- A mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), iron oxide, titanium oxide, Prussian blue, alizarin dye, azo dye, and phthalocyanine dye.

  The arthropod pest control agent of the present invention is obtained by mixing a formulation of an oxadiazine compound represented by the formula (A) with a formulation of an ester compound represented by the formula (B) depending on the formulation. Can also be prepared, and can be mixed at the time of application.

  In the method for controlling harmful arthropods of the present invention, the agent for controlling harmful arthropods of the present invention is usually applied to harmful arthropods or habitats of harmful arthropods (plants, soil, houses, animals, etc.). It is carried out by application, but without mixing the oxadiazine compound represented by the formula (A) or the preparation thereof and the ester compound represented by the formula (B) or the preparation thereof at the same time, the harmful arthropod or harmful It can also be applied to arthropod habitats. In this case, the ratio of the oxadiazine compound represented by the formula (A) and the ester compound represented by the formula (B) is usually 50: 1 to 1:10 by weight, preferably 20: 1 to 1: 1. 1: 4 ratio.

When the arthropod pest controlling agent of the present invention is used for controlling arthropod pests in the agricultural field, the application rate is the oxadiazine compound represented by the formula (A) and the ester compound represented by the formula (B) per 10,000 m ^2. Is usually 1 to 10,000 g. When the arthropod pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, and the like, it is usually diluted with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm, and applied. Granules, powders and the like are usually applied as they are.
These preparations and aqueous dilutions of these preparations may be applied directly to plants such as harmful arthropods or crops to be protected from harmful arthropods, or harmful arthropods that inhabit cultivated soil. The soil may be treated to control it.
Alternatively, the resin preparation processed into a sheet or a string can be treated by a method such as wrapping it around a crop, spreading it around a crop, or laying it on a stock soil.

When the arthropod pest control agent of the present invention is used for controlling arthropod pests (for example, flies, mosquitoes, cockroaches) living in homes, the application rate is 1 m ² when treated on a surface. is usually 0.01~1000mg a total amount of the ester compound represented by the oxadiazine compounds represented by the formula formula per (a) (B), formula per processing space 1 m ³ if the process in the space (a )) And the ester compound represented by the formula (B) in a total amount of usually 0.01 to 500 mg. When the arthropod pest control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable or the like, it is usually diluted with water so that the active ingredient concentration becomes 0.1 to 1000 ppm, and applied. Oils, aerosols, smokers, poison baits, sheet preparations, etc. are applied as they are.

When the harmful arthropod controlling agent of the present invention is used for controlling harmful arthropods (for example, termites) that damage woody materials, the harmful arthropod controlling agent of the present invention is used for controlling harmful arthropods that damage woody materials. It is applied to woody materials such as habitats of arthropod pests that inflict materials or building materials. At the time of application, it is applied (usually 0.01 to 30 g / m ² in the total amount of the oxadiazine compound represented by the formula (A) and the ester compound represented by the formula (B)), and sprayed (represented by the formula (A)). The total amount of the oxadiazine compound and the ester compound represented by the formula (B) is usually 0.1 to 300 g / m ² ), and the mixture with an adhesive (the oxadiazine compound represented by the formula (A) and the formula (B)) Usually, a method such as 0.1 to 100 g / m ³ ) in total amount with the ester compound is employed.

  When the arthropod pest control agent of the present invention is used for ectoparasitic pest control of animals (pets such as dogs and cats; livestock such as cattle and sheep), the arthropod pest control agent of the present invention is applied to animals. It is applied by a method such as washing an animal with the pest control agent of the present invention. In this case, the application rate is usually 0.1 to 1000 mg in terms of the total amount of the oxadiazine compound represented by the formula (A) and the ester compound represented by the formula (B) per 1 kg of the body weight of the animal.

  The arthropod pest control agent of the present invention can be used together with other pesticidal active ingredients and / or synergists such as PBO, S-421, MGK-264, IBTA, and sinepirin 500.

  Hereinafter, the present invention will be described in more detail with reference to formulation examples and test examples, but the present invention is not limited to these examples.

First, formulation examples are shown. Parts represent parts by weight.
Formulation Example 1
An emulsion is obtained by mixing 2.5 parts of compound (A); 2.5 parts of compound (B); 8 parts of polyoxyethylene styryl phenyl ether; 2 parts of calcium dodecylbenzenesulfonate; and 85 parts of xylene.

Formulation Example 2
10 parts of compound (A); 10 parts of compound (B); 3 parts of sodium dodecylbenzenesulfonate; 3 parts of sodium ligninsulfonate; and 74 parts of diatomaceous earth are uniformly mixed and pulverized by a jet air mill to obtain a wettable powder.

Formulation Example 3
A powder is obtained by uniformly mixing and stirring 1 part of compound (A); 1 part of compound (B); 48 parts of talc; and 50 parts of clay.

Formulation Example 4
To 10 parts of the compound (A) and 5 parts of the compound (B), 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 50 parts of clay are added and sufficiently stirred and mixed. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain granules.

Formulation Example 5
5 parts of polyoxyethylene styryl phenyl ether sulfate, 20 parts of a 1% xanthan gum aqueous solution, 3 parts of smectite mineral and 57 parts of water are uniformly mixed, and 10 parts of compound (A) and 5 parts of compound (B) are added thereto. After stirring well, wet pulverization is performed with a sand mill to obtain a flowable agent.

Formulation Example 6
0.2 part of the compound (A) and 0.1 part of the compound (B) are dissolved in 59.7 parts of deodorized kerosene and placed in an aerosol container. A valve is attached to the aerosol container, and 40 parts of liquefied petroleum gas (LPG) is filled under pressure through the valve portion to obtain an oily aerosol.

Formulation Example 7
0.1 part of compound (A); 0.2 part of compound (B); 5 parts of xylene; and 5 parts of trichloroethane are mixed, and 89.7 parts of deodorized kerosene is added to the mixture to obtain an oil agent.

Next, the efficacy of the arthropod pest control agent of the present invention is shown by test examples.
Test example 1
Indoxacarb MP (hereinafter, referred to as a first component), imiprothrin (hereinafter, referred to as a second component), 2 g each, and xylene / solpol SM200X (surfactant; Toho Chemical Industry Co., Ltd.) = 85/15 The mixture was mixed with 98 g of the mixture to obtain a preparation of the first component and a preparation of the second component. The preparation of the first component and the preparation of the second component were mixed at a predetermined ratio to obtain a test preparation. This test preparation was diluted to a predetermined concentration with water to prepare a test drug solution.
On the other hand, a wooden triangular prism container (3.5 cm square, 15 cm high) is placed vertically in the center of the lower part of a cubic glass box with a side of 70 cm, and 10 German cockroaches (5 males and 5 females) are placed in this container. I put it. This glass box was sprayed with 4.2 ml of the test solution using a spray gun. Ten minutes after the treatment, the German cockroach was transferred to a plastic container containing food and water, and left for 4 days. Thereafter, the life and death of German cockroaches were observed, and the mortality was determined. Table 1 shows the results.

Test example 2
Twenty adult houseflies (10 males and 10 females) were released into a cubic glass box having a side of 70 cm. Into this glass box, 2.1 ml of a test drug solution prepared in the same manner as in Test Example 1 was sprayed using a spray gun. Ten minutes after the treatment, the house flies were transferred to a plastic container containing food and water and allowed to stand for 2 days. Then, the survival of the house fly was observed, and the mortality was determined. Table 2 shows the results.

Test example 3
Twenty adult female Culex pipiens were released into a cubic glass box 70 cm on a side. Into this glass box, 2.1 ml of a test drug solution prepared in the same manner as in Test Example 1 was sprayed using a spray gun. Ten minutes after the treatment, Culex pipiens was transferred to a plastic container containing food and water and left for 1 day. Thereafter, the life and death of Culex pipiens was observed, and the mortality was determined. Table 3 shows the results.

Test example 4
10 ml of a test drug solution having a predetermined concentration prepared in the same manner as in Test Example 1 and 200 g of sterilized soil were mixed and allowed to stand for 24 hours. The soil was transferred to a petri dish having a diameter of 9 cm, and ten termite termites were released there and left for 3 days. Thereafter, the termites were observed for life and death, and the mortality was determined. Table 4 shows the results.

Test example 5
0.05 g of the first component and 0.05 g of the second component were dissolved in 49.9 g of deodorized kerosene and placed in an aerosol container. A valve was attached to the aerosol container, and 50 g of dimethyl ether was charged under pressure through the valve to obtain a test aerosol.
On the other hand, 50 g of soil was placed in a plastic container having a diameter of 10 cm and a height of 4.6 cm, and 10 ants were released on the soil. From above 60 cm of the plastic container, 0.2 g of the test aerosol was sprayed. After the treatment, the food was put in a plastic container and left for 3 days. Thereafter, when the life and death of the ant was observed, the mortality was 100%.

  The arthropod pest control agent of the present invention has an excellent arthropod pest control effect and is therefore useful for controlling arthropod pests.

Claims (4)

Formula (A)

An oxadiazine compound represented by the formula (B):

A harmful arthropod controlling agent comprising an ester compound represented by the formula (1) as an active ingredient. The harmful arthropod controlling agent according to claim 1, wherein the weight ratio of the oxadiazine compound represented by the formula (A) to the ester compound represented by the formula (B) is in the range of 50: 1 to 1:10. Formula (A)

An oxadiazine compound represented by the formula (B):

A method for controlling harmful arthropods, which comprises applying an effective amount of the harmful arthropods to the harmful arthropods or the habitats of the harmful arthropods. The method for controlling arthropod pests according to claim 3, wherein the weight ratio of the oxadiazine compound represented by the formula (A) to the ester compound represented by the formula (B) is in the range of 50: 1 to 1:10.