JP2004137259A - Vermin-controlling composition and method for controlling vermin - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a horticulturally useful vermin-controlling composition. <P>SOLUTION: This vermin-controlling composition contains (a) at least one kind of a hydrazone-based compound expressed by formula (I) or its salt, and (b) 2-methylbiphenyl-3-ylmethyl=(Z)-(1RS, 3RS)-3-(2-chloro-3, 3, 3-trifluoroprope-1-enyl)-2, 2-dimethylcyclopropane carboxylate and/or a BT agent as active ingredients. <P>COPYRIGHT: (C)2004,JPO

Description

The present invention relates to an agricultural and horticulturally useful pest controlling composition comprising (a) a combination of a hydrazone compound represented by the following formula (I) or a salt thereof and (b) bifenthrin and / or a specific BT agent. . The present invention also relates to a method for controlling pests, which comprises causing each of the active ingredients (a) and (b) to act on pests.

The hydrazone-based compound represented by the following formula (I) or a salt thereof is a compound useful as an insecticide, and is described in US Pat. No. 5,288,727. Japanese Patent No. 3071962 describes a pest controlling composition containing a compound of the formula (I) described below and another active ingredient. However, they do not disclose the pest controlling composition of the present invention.

U.S. Pat. No. 5,288,727 Patent No. 3071962

Conventional pesticides have characteristics in terms of spectrum and effect, however, on the other hand, on the other hand, the effect is not sufficient for specific pests, or the residual effect is short and the effect for a certain period cannot be expected. Therefore, depending on the application scene, practically sufficient control effect may not be exhibited. Further, even if they have excellent control effects, improvements are required from the viewpoint of safety against fish, crustaceans and livestock, and high control effects are required with a small amount of treatment chemicals. Furthermore, some insecticides induce resurgence (outbreak after application) of specific pests, and improvement is required.

The present inventors have conducted various studies to solve these problems, and as a result, by combining a hydrazone-based compound represented by the following formula (I) or a salt thereof with a known pest control agent, the occurrence of the hydrazone-based compound in a certain scene is considered. It is possible to control the pests at once, or to reduce the amount of drug used compared to the case where each active ingredient compound is used alone, the knowledge that more than expected effect is obtained, The present invention has been completed. That is, the present invention relates to (a) the formula (I)

（式中、Ｒ^１、Ｒ^２及びＲ^４は各々独立して、水素原子、ハロゲン原子、ハロゲン原子で置換されてもよいアルキル基又はハロゲン原子で置換されてもよいアルコキシ基であり；Ｒ^３はハロゲン原子、ハロゲン原子で置換されてもよいアルキル基又はハロゲン原子で置換されてもよいアルコキシ基であり；Ｒ^５は水素原子又はアルキル基であり；Ｒ^６はＸ^７ＣＯ−基（Ｘ^７は水素原子又はアルキル基である）又はＸ^８ＯＣＯ−基（Ｘ^８はアルキル基である）であるか又はＲ^５とＲ^６が一緒になって、＝ＣＲ^７Ｒ^８基を形成してもよく；
Ｒ^７は水素原子又はアルキル基であり；Ｒ^８はアルキル基で置換されてもよいアミノ基又はアルコキシ基である）で表わされるヒドラゾン系化合物又はそれらの塩の少なくとも１種と、(b)（b-1）２−メチルビフェニル−３−イルメチル＝（Ｚ）−（１ＲＳ，３ＲＳ）−３−（２−クロロ−３，３，３−トリフルオロプロペ−１−エニル）−２，２−ジメチルシクロプロパンカルボキシラート及び／又は(b-2)クルスターキ菌の死菌、クルスターキ菌の生菌、アイザワイ菌の死菌、アイザワイ菌の生菌及びクルスターキ菌とアイザワイ菌が接合した変異株（生菌）から成る群から選択される少なくとも1種のＢＴ剤とを有効成分として含有することを特徴とする有害生物防除用組成物に関する。

(Wherein R ¹ , R ² and R ⁴ are each independently a hydrogen atom, a halogen atom, an alkyl group optionally substituted with a halogen atom or an alkoxy group optionally substituted with a halogen atom; R ³ Is a halogen atom, an alkyl group optionally substituted with a halogen atom or an alkoxy group optionally substituted with a halogen atom; R ⁵ is a hydrogen atom or an alkyl group; R ⁶ is an X ⁷ CO— group (X ⁷ Is a hydrogen atom or an alkyl group) or an X ⁸ OCO— group (X ⁸ is an alkyl group), or R ⁵ and R ⁶ together form a ＣＲCR ⁷ R ⁸ group Often;
R ⁷ is a hydrogen atom or an alkyl group; R ⁸ is an amino group or an alkoxy group which may be substituted with an alkyl group), or at least one of salts thereof, and (b) ( b-1) 2-Methylbiphenyl-3-ylmethyl = (Z)-(1RS, 3RS) -3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethyl Cyclopropane carboxylate and / or (b-2) killed bacteria of C. crustarch, viable bacteria of C. lucifera, killed bacteria of I. bacillus, and viable strains of C. bacterium and bacterium of I. C. cruzi (live bacteria) A pest control composition comprising as an active ingredient at least one BT agent selected from the group consisting of:

The alkyl group or alkyl moiety contained in the formula (I) has 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and the like, and is an alkenyl group or an alkenyl group. The moiety has 2 to 6 carbon atoms, for example, a vinyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group and the like, and the alkynyl group or the alkynyl moiety has 2 to 6 carbon atoms, for example, an ethynyl group, Examples thereof include a propynyl group, a butynyl group, a pentynyl group, and a hexynyl group, and the above-mentioned groups or parts include those having linear or branched aliphatic chains having structural isomerism. Further, examples of the halogen atom contained in the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

The following compounds are most desirable among the compounds represented by the formula (I).
[4'-chloro-2- (4-trifluoromethylphenyl) acetophenone] N '-[1- (dimethylamino) ethylidene] hydrazone (compound No. 1),
[4'-fluoro-2- (4-trifluoromethylphenyl) acetophenone] N '-[1- (dimethylamino) ethylidene] hydrazone (compound No. 2),
Ethyl 3- [1- (4-chlorophenyl) -2- (4-trifluoromethylphenyl) ethylidene] carbazate (Compound No. 3),
[4'-chloro-2- (4-tert-butylphenyl) acetophenone] N '-[1- (dimethylamino) ethylidene] hydrazone (compound No. 4),
[4'-fluoro-2- (4-tert-butylphenyl) acetophenone] N '-[1- (dimethylamino) ethylidene] hydrazone (compound No. 5),
[4'-methyl-2- (4-tert-butylphenyl) acetophenone] N '-[1- (dimethylamino) ethylidene] hydrazone (compound No. 6),
[4'-chloro-2- (4-trifluoromethylphenyl) acetophenone] N '-[1-aminoethylidene] hydrazone (Compound No. 7),
[4'-Fluoro-2- (4-trifluoromethylphenyl) acetophenone] N '-[1-aminoethylidene] hydrazone (Compound No. 8)

化合物 The compound represented by the formula (I) can take a salt with an acidic substance or a basic substance. Examples of the salt with the acidic substance include inorganic salts such as hydrochloride and sulfate, and examples of the salt with the basic substance include sodium salt, potassium salt, calcium salt, ammonium salt and dimethylamine salt. And a salt with an inorganic base or an organic base.

Further, in the compound represented by the formula (I), since a hydrazone has a double bond, geometric isomers of E-form and Z-form exist, and each of these isomers and a mixture of each isomer are represented by Included in the invention.

The hydrazone compound represented by the formula (I) or a salt thereof can be produced according to the method described in US Pat. No. 5,288,727.

As the active ingredient (b) of the pest controlling composition of the present invention, (b-1) 2-methylbiphenyl-3-ylmethyl = (Z)-(1RS, 3RS) -3- (2-chloro-3) , 3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate [generic name: bifenthrin, trade name: Talstar] and / or (b-2) At least one BT agent selected from the group consisting of killed bacteria, live bacteria of Klustarki, killed bacteria of Aisai fungus, live bacteria of Aisai fungus, and mutants (live bacteria) in which Klustarki and Aisawai are conjugated. Can be

The BT agent is an insecticide containing as an active ingredient a crystal toxin produced in a bacterium belonging to Bacillus thuringiensis Berliner. Specific examples of dead bacteria of Kurstaki bacteria include trade name trade arrow and trade name guard jet. Specific examples of viable bacteria of Klustarki include dipole, trade name Thulicide, trade name Delfin, trade name Esmarck, trade name tune-up, and the like. Specific examples of killed bacteria of Aizawai include trade name Repetitum. Specific examples of the viable bacteria of the Isaiwai bacterium include Select Gin, trade name Zentari, trade name Quark, trade name Flowback, and the like. Specific examples of mutant strains (live bacteria) obtained by conjugation of Klestarki bacteria and Aisawai bacteria include trade name Basilex, trade name Biosh, trade name Two Bit, and the like. Among these BT agents, it is most desirable to use dead bacteria of Klusterki.

混合 The mixing ratio of the active ingredient (a) and the active ingredient (b) in the present invention is 1: 100 to 100: 1, preferably 1:50 to 50: 1. In the composition for controlling pests of the present invention, 2-methylbiphenyl-3-ylmethyl = (Z)-(1RS, 3RS) -3- (2-chloro-3,3,3-triethyl) is used as the active ingredient (b). In the case of using (fluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate, an emulsion, a powder, a granule, a wettable powder, and a granule water are used together with the pesticide auxiliary in the same manner as in the case of the conventional pesticide formulation. It can be formulated in various forms such as a sump, suspension, liquid, aerosol, paste and the like. When a BT agent is used as the active ingredient (b), it can be formulated in the form of a wettable powder, a water-dispersible granule, an aqueous suspension and the like. The mixing ratio of these active ingredients is usually 0.1 to 90 parts by weight, preferably 0.5 to 90 parts by weight, more preferably 0.5 to 80 parts by weight, and 10 to 99.9 parts by weight of the pesticide adjuvant, preferably 0.5 to 80 parts by weight. Is 10 to 99.5 parts by weight, more preferably 20 to 99.5 parts by weight. When these preparations are actually used, they can be used as they are or diluted to a predetermined concentration with a diluent such as water.

Examples of the pesticide auxiliary herein include a carrier, an emulsifier, a suspending agent, a dispersing agent, a spreading agent, a penetrating agent, a wetting agent, a thickener, an antifoaming agent, a stabilizer, an antifreezing agent, and the like. May be added as appropriate. The carrier is divided into a solid carrier and a liquid carrier, and as the solid carrier, starch, activated carbon, soybean flour, wheat flour, wood flour, fish flour, animal and plant powders such as milk powder, talc, kaolin, bentonite, calcium carbonate, zeolite, Mineral powders such as diatomaceous earth, white carbon, clay, and alumina, sulfur powders, anhydrous sodium sulfate, and the like. Examples of liquid carriers include water, alcohols such as methyl alcohol and ethylene glycol, acetone, methyl ethyl ketone, and N-methyl-. Ketones such as 2-pyrrolidone, ethers such as dioxane and tetrahydrofuran, kerosene, aliphatic hydrocarbons such as kerosene, xylene, trimethylbenzene, tetramethylbenzene, cyclohexane, aromatic hydrocarbons such as solvent naphtha, chloroform, Chlorobenzene Halogenated hydrocarbons, acid amides such as dimethylformamide, ethyl acetate, esters such as glycerin ester of fatty acid, nitriles such as acetonitrile, sulfur-containing compounds such as dimethyl sulfoxide, soybean oil, corn oil and the like. Vegetable oils and the like.

The composition for controlling pests of the present invention may be prepared by mixing active ingredients, or may be prepared by mixing each active ingredient in advance. The composition for controlling pests of the present invention has a controlling effect on insects, mites and nematodes which are harmful on agricultural and horticultural purposes. In particular, for the control of lepidopteran pests, such as squid, moth flies, awanomeiga, konaga, tosuminomito, shirochimojiyoto, and locusts; Hemiptera pests such as aphids and leafhoppers; beetle pests such as leaf beetles; It is valid.

When the pest controlling composition of the present invention is applied, the active ingredient (a) is generally used in an amount of 1 to 100,000 ppm, preferably 1 to 50,000 ppm, more preferably 10 to 20,000 ppm, and the active ingredient (b). Is generally carried out at a concentration of each active ingredient of 1 to 100,000 ppm, preferably 1 to 50,000 ppm, more preferably 10 to 20,000 ppm. The concentration of these active ingredients may deviate from these ranges depending on the form of the preparation, the method of application, the purpose, the time, the place and the occurrence of pests. For example, in the case of aquatic pests, even if a chemical solution having the above concentration range is sprayed on the place of occurrence, control can be carried out. Therefore, the concentration range of the active ingredient in water is as follows. The application rate per unit area is such that the active ingredient (a) is used in an amount of about 1 to 50,000 g, preferably 10 to 10,000 g, and the active ingredient (b) is used in an amount of about 1 to 50,000 g, preferably 1 ha. Is used in an amount of 10 to 10,000 g. However, in special cases, it is possible to deviate from these ranges. In addition, the application is carried out by a generally used method, that is, spraying (eg, spraying, spraying, misting, atomizing, granulation, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application) , Dressing, coating, etc.), immersion poison bait and the like. In addition, it is also possible to feed the livestock with the above-mentioned active ingredient mixed with the feed to control the development and growth of harmful insects, especially harmful insects, in the excrement. It can also be applied by the so-called ultra low volume method. In this method, it is possible to contain 100% of the active ingredient.

製 剤 Formulation examples of the pest controlling composition of the present invention will be described, but the types, blending ratios, dosage forms, etc. of the active ingredient compound and the pesticide auxiliary are not limited to the description examples only.

<Formulation Example 1>
(A) Compound No. 23 parts by weight (b) 1.5% by weight of bifenthrin (c) 95.5 parts by weight or more of talc are uniformly mixed to form a powder.

<Formulation Example 2>
(A) Compound No. 5 20 parts by weight (b) Bifenthrin 10 parts by weight (c) Oxylated polyalkylphenol phosphatotriethanolamine 2 parts by weight (d) Silicone 0.2 parts by weight (e) Xanthan gum 0.1 parts by weight (f) Ethylene Glycol 5 parts by weight (g) Water 62.7 parts by weight or more are uniformly mixed and pulverized to obtain an aqueous suspension.

<Formulation Example 3>
(A) Compound No. 25 parts by weight (b) 5 parts by weight of bifenthrin (c) 33 parts by weight of bentonite (d) 52 parts by weight of kaolin (e) 5 parts by weight of sodium ligninsulfonate An appropriate amount of required granulation water is added to each component and mixed. Granulation is performed to obtain granules.

<Formulation Example 4>
(A) Compound No. 52 2 parts by weight (b) Bifenthrin 0.5 parts by weight (c) N-methyl-2-pyrrolidone 2.5 parts by weight (d) Soybean oil 95.0 parts by weight or more uniformly mixed, dissolved and trace amount Spray (ultra low volume formulation).

<Formulation Example 5>
(A) Compound No. 8 10 parts by weight (b) Bifenthrin 10 parts by weight (c) Corn oil 67 parts by weight (d) Polyoxyethylene hydrogenated castor oil 12 parts by weight (e) Organic bentonite 1 part by weight or more is uniformly mixed and pulverized. A suspension is obtained.

<Formulation Example 6>
(A) Compound No. 13 parts by weight (b) Bifenthrin 2 parts by weight (c) Talc 95 parts by weight or more are uniformly mixed to form a powder.

<Formulation Example 7>
(A) Compound No. 53 parts by weight (b) 0.5 parts by weight of bifenthrin (c) 96.5 parts by weight or more of talc are uniformly mixed to prepare a powder.

<Formulation Example 8>
(A) Compound No. 83 parts by weight (b) Bifenthrin 2 parts by weight (c) Clay 95 parts by weight or more are uniformly mixed to give a powder.

<Formulation Example 9>
(A) Compound No. 13 parts by weight
(B) 0.3 parts by weight of bifenthrin (c) 96.7 parts by weight or more of talc are uniformly mixed to obtain a powder.

Next, test examples will be described.

<Test Example 1 (Ponifera insecticidal test)>
To a pot-planted Chinese cabbage (variety: Muso), a sufficient amount of the chemical solution adjusted to a predetermined concentration is sprayed with foliage using an automatic sprayer, and after 7 days, the treated pot-planted Chinese cabbage is placed in a cylindrical wire netting, and then 3rd-year-old Konaga Twenty terminal larvae were released, covered and managed in a greenhouse. Six days after the release, the number of dead insects was examined. Each test was performed twice, and the mortality was calculated as the average value, and the results are shown in Table 1.
The theoretical value (%) of the mortality can be calculated by the following Colby's formula. When the mortality (%) is higher than the theoretical value (%) according to Colby's formula, the pest controlling composition of the present invention has a synergistic effect with respect to the control of agricultural pests. The theoretical value (%) according to Colby's equation in such a case is also shown in parentheses in Table 1.
Theoretical value (%) = 100− (X × Y) / 100
X: 100-[Death rate when only hydrazone compound is treated]
Y: 100-[Death rate when only bifenthrin is treated]

<Test Example 2 (Spodoptera litura insecticidal test)>
A pot of cabbage (cultivar: Okina) was sprayed with foliage in an amount sufficient to adjust the concentration to a predetermined concentration using an automatic sprayer and managed in a greenhouse. Three days after spraying, the cabbage leaves were cut and placed in a plastic petri dish with a diameter of 9 cm covered with moist filter paper. Ten larvae of the third stage of the cutworm, Spodoptera litura, were released, capped, and placed in a constant temperature room at 26 ° C. Four days after the release, the number of dead insects was examined. Each test was performed twice, and the mortality was calculated as the average value, and the results are shown in Table 2.
The theoretical value (%) of the mortality can be calculated by the following Colby's formula. When the mortality (%) is higher than the theoretical value (%) according to Colby's formula, the pest controlling composition of the present invention has a synergistic effect with respect to the control of agricultural pests. The theoretical value (%) according to Colby's equation in such a case is also shown in parentheses in Table 2.
Theoretical value (%) = 100− (X × Y) / 100
X: 100-[Death rate when only hydrazone compound is treated]
Y: 100-[Death rate when only bifenthrin is treated]

<Test Example 3 (Spodoptera litura insecticidal test)>
A pot of cabbage (cultivar: Okina) was sprayed with foliage in an amount sufficient to adjust the concentration to a predetermined concentration using an automatic sprayer and managed in a greenhouse. Three days after spraying, the cabbage leaves were cut and placed in a plastic petri dish with a diameter of 9 cm covered with moist filter paper. Ten larvae of the third stage of the cutworm, Spodoptera litura, were released, capped, and placed in a constant temperature room at 26 ° C. Four days after the release, the number of dead insects was examined. Each test was performed twice, and the mortality was calculated as the average value, and the results are shown in Table 3.
The theoretical value (%) of the mortality can be calculated by the following Colby's formula. When the mortality (%) is higher than the theoretical value (%) according to Colby's formula, the pest controlling composition of the present invention has a synergistic effect with respect to the control of agricultural pests. The theoretical value (%) according to Colby's equation in such a case is also shown in parentheses in Table 3.
Theoretical value (%) = 100− (X × Y) / 100
X: 100-[Death rate when only hydrazone compound is treated]
Y: 100-[Death rate when only Torow CT WP is treated]

<Test Example 4 (Effect of controlling damage to Spodoptera litura)>
To a cabbage (variety: Okina) planted in a transparent plastic pot with a diameter of 13 cm, a sufficient amount of the chemical solution (20 ml / strain) adjusted to a predetermined concentration is sprayed with foliage using an automatic sprayer, air-dried, and then treated in a cylindrical wire net. The cabbage was put into the cabbage, and ten larvae of the third generation of the cutworm, Spodoptera litura, were released, covered, and placed in a breeding room at 25 ° C. Five days after the release, the cabbage was examined for food damage, and the food damage inhibitory effect (index) was calculated by the following formula. The test was performed in a two-part system.
Eating control effect (index) = 100-(index when untreated area is set to 100)
In addition, the theoretical value (index) of the feeding damage suppressing effect can be calculated by Colby's formula. When the food damage control effect (index) is higher than the theoretical value (index) according to Colby's formula, the pest control composition of the present invention has a synergistic effect with respect to the control of agricultural pests. The theoretical value (index) based on Colby's equation in such a case is also shown in parentheses in Table 4.

Claims (5)

(a) Formula (I):

(Wherein R ¹ , R ² and R ⁴ are each independently a hydrogen atom, a halogen atom, an alkyl group optionally substituted with a halogen atom or an alkoxy group optionally substituted with a halogen atom; R ³ Is a halogen atom, an alkyl group optionally substituted with a halogen atom or an alkoxy group optionally substituted with a halogen atom; R ⁵ is a hydrogen atom or an alkyl group; R ⁶ is an X ⁷ CO— group (X ⁷ Is a hydrogen atom or an alkyl group) or an X ⁸ OCO— group (X ⁸ is an alkyl group), or R ⁵ and R ⁶ together form a ＣＲCR ⁷ R ⁸ group well; R ⁷ is a hydrogen atom or an alkyl group; R ⁸ is at least one hydrazone compound or salts thereof represented by the alkyl is an amino group or an alkoxy group which may be substituted with group), (b ) (B-1 2-methylbiphenyl-3-ylmethyl = (Z)-(1RS, 3RS) -3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate And / or (b-2) a group consisting of dead bacteria of Klustarki bacteria, live bacteria of Klustarki bacteria, killed bacteria of Izawai bacteria, live bacteria of Izawai bacteria, and mutants (live bacteria) in which Klustarki and Izawai bacteria are conjugated. A pesticidal composition comprising at least one selected BT agent as an active ingredient. When the active ingredient (a) is [4′-chloro-2- (4-trifluoromethylphenyl) acetophenone] N ′-[1- (dimethylamino) ethylidene] hydrazone, [4′-fluoro-2- (4- [Trifluoromethylphenyl) acetophenone] N '-[1- (dimethylamino) ethylidene] hydrazone, ethyl 3- [1- (4-chlorophenyl) -2- (4-trifluoromethylphenyl) ethylidene] carbazate, [4' -Chloro-2- (4-tert-butylphenyl) acetophenone] N '-[1- (dimethylamino) ethylidene] hydrazone, [4'-fluoro-2- (4-tert-butylphenyl) acetophenone] N'- [1- (Dimethylamino) ethylidene] hydrazone, [4′-methyl-2- (4-tert-butylphenyl) Acetophenone] N '-[1- (dimethylamino) ethylidene] hydrazone, [4'-chloro-2- (4-trifluoromethylphenyl) acetophenone] N'-[1-aminoethylidene] hydrazone and [4 ' The pest according to claim 1, which is at least one hydrazone compound selected from the group consisting of -fluoro-2- (4-trifluoromethylphenyl) acetophenone] N '-[1-aminoethylidene] hydrazone or a salt thereof. A composition for controlling. When the active ingredient (b) is 2-methylbiphenyl-3-ylmethyl = (Z)-(1RS, 3RS) -3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2,2 The composition for controlling pests according to claim 1, which is -dimethylcyclopropanecarboxylate. The pest controlling composition according to claim 4, wherein the active ingredient (b) is a killed bacterium of Klusterki. A method for controlling pests, comprising causing an effective amount of the active ingredient (a) and the active ingredient (b) according to claim 1 to act on pests.