WO2016002595A1 - Pest control composition and use for same - Google Patents

Abstract

A pest control composition containing a compound expressed in formula (1) (in which the symbols are as defined in the specification), and a 2,4-dioxo-1-(5-pyrimidinylmethyl)-3-[3-(trifluoromethyl)phenyl]-2H-pyrid[1, 2-a] pyrimidinium inner salt has exceptional control efficacy against pests. Provided is a pest control composition having exceptional control efficacy against pests.

Description

Pest control composition and use thereof

The present invention relates to a pest control composition and a pest control method.

Conventionally, many compounds are known as active ingredients of pest control compositions (see, for example, Non-Patent Document 1).

International Publication No. 2013/018928 International Publication No. 2012/092115 International Publication No. 2014/104407

An object of the present invention is to provide a pest control composition having an excellent control effect against pests.

As a result of studies to find a pest control composition having an excellent control effect against pests, the present inventor has found that a compound represented by the following formula (1) and 2,4-dioxo-1- (5-pyrimidinylmethyl) ) -3- [3- (trifluoromethyl) phenyl] -2H-pyrido [1,2-a] pyrimidinium inner salt (hereinafter referred to as Triflumezopyrim) is harmful It has been found that it has an excellent control effect on organisms.

The present invention is as follows.
Item 1. Formula (1):

[Where:
A ¹ represents —NR ⁷ —, an oxygen atom or a sulfur atom, A ² represents ═N—, ═N (→ O) — or ═CR ⁸ —, and Q represents ═N— or ═N (→ O). R ¹ represents a C1-C6 alkyl group optionally having one or more atoms or groups selected from Group X, and R ² , R ³ and R ⁴ are the same or different, A C1-C6 alkyl group optionally having one or more atoms or groups selected from the group: —OR ¹⁰ , —S (O) _m R ¹⁰ , —S (O) ₂ NR ¹⁰ R ¹¹ , —NR ¹⁰ R ¹¹ , —NR ¹⁰ CO ₂ R ¹¹ , —NR ¹⁰ C (O) R ¹¹ , —CO ₂ R ¹⁰ , —C (O) R ¹⁰ , —C (O) NR ¹⁰ R ¹¹ , —SF ₅ , cyano Group, nitro group, halogen atom or hydrogen atom, R ⁵ and R ⁶ are the same or different and selected from group X A C1-C6 alkyl group optionally having one or more atoms or groups, —OR ¹⁰ , —S (O) _m R ¹⁰ , —S (O) ₂ NR ¹⁰ R ¹¹ , —NR ¹⁰ R ¹¹ , —NR ¹⁰ CO ₂ R ¹¹ , —NR ¹⁰ C (O) R ¹¹ , —CO ₂ R ¹⁰ , —C (O) R ¹⁰ , —C (O) NR ¹⁰ R ¹¹ , —OC (O) R ¹⁰ , —SF ₅ , a cyano group, a nitro group, a halogen atom or a hydrogen atom (provided that R ⁵ and R ⁶ do not simultaneously represent a hydrogen atom), R ⁷ represents one or more atoms selected from the group W Or an optionally substituted C1-C6 alkyl group, —CO ₂ R ¹⁰ , —C (O) R ¹⁰ , —CH ₂ CO ₂ R ¹⁰ , a C3-C6 cycloalkyl group or a hydrogen atom; ⁸ may have one or more halogen atoms C -C6 alkyl ^{group, -OR 10, -S (O)} m R 10, -NR 10 R 11, -CO 2 R 10, -C (O) R 10, a cyano group, a nitro group, a halogen atom or a hydrogen atom R ¹⁰ and R ¹¹ are the same or different and each represents a C1-C6 alkyl group or a hydrogen atom which may have one or more atoms or groups selected from Group X (provided that —S (O) _{m In} R ¹⁰ , when m is 1 or 2, R ¹⁰ does not represent a hydrogen atom), m independently represents 0, 1 or 2, and n represents 0, 1 or 2 To express. Group X: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 cycloalkyl optionally having one or more halogen atoms or one or more C1-C3 alkyl groups A group consisting of a group, a cyano group, a hydroxy group and a halogen atom.
Group W: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 cycloalkyl group optionally having one or more halogen atoms, hydroxy group, halogen atom and cyano group A group consisting of And a 2,4-dioxo-1- (5-pyrimidinylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H-pyrido [1,2-a] pyrimidinium inner salt ( Pest control composition containing triflumezopyrine) (hereinafter referred to as the present composition).
Item 2. A ¹ is —NMe—, an oxygen atom or a sulfur atom, A ² is ═N—, ═N (→ O) — or ═CH—, and R ¹ has one or more halogen atoms. A C1-C6 alkyl group, R ² and R ⁴ are hydrogen atoms, R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms or a hydrogen atom, and R ⁵ Is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR ¹⁰ , or —S (O) _m R ¹⁰ , R ⁶ is —NR ¹⁰ R ¹¹ or a hydrogen atom, Item 2. The pest control composition according to Item 1, wherein R ¹⁰ and R ¹¹ are each independently a C1-C3 alkyl group optionally having one or more halogen atoms.
Item 3. Item 3. The pest control composition according to Item 1 or 2, wherein A ¹ is -NMe-.
Item 4. Item 3. The pest control composition according to Item 1 or 2, wherein A ¹ is an oxygen atom.
Item 5. A compound represented by the formula (1) and a 2,4-dioxo-1- (5-pyrimidinylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H-pyrido [1,2-a] pyrimidinium molecule Item 5. The pest control composition according to any one of Items 1 to 4, wherein the content ratio with the inner salt is 100: 1 to 1: 100 by weight.
Item 6. A compound represented by the formula (1) and a 2,4-dioxo-1- (5-pyrimidinylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H-pyrido [1,2-a] pyrimidinium molecule The pesticidal composition according to any one of claims 1 to 4, wherein the content ratio with the inner salt is 10: 1 to 1:10 by weight.
Item 7. Item 7. A pest control method comprising a step of applying an effective amount of the pest control composition according to any one of Items 1 to 6 to a pest or a habitat of the pest.
Item 8. Item 7. A method for controlling pests, comprising a step of applying an effective amount of the pest control composition according to any one of Items 1 to 6 to a plant, plant seeds, bulbs, or soil in which plants are grown.
Item 9. Item 7. A plant seed or bulb to which an effective amount of the pesticidal composition according to any one of Items 1 to 6 is attached.

According to the present invention, pests can be controlled.

The pest control composition of the present invention contains a compound represented by the above formula (1) (hereinafter sometimes referred to as the present compound) and triflumezopyrim.

The groups used in the description of this specification will be described below.

The notation of a Ca—Cb alkyl group in the present specification represents a linear or branched hydrocarbon group having a carbon number of a to b,
The notation of the Ca—Cb haloalkyl group represents a linear or branched hydrocarbon group having a carbon number of a to b in which one or more hydrogen atoms bonded to a carbon atom are substituted with a halogen atom, At this time, when having two or more halogen atoms, those halogen atoms may be the same or different from each other,
The notation of the Ca—Cb alkoxy group represents a linear or branched alkyl-O— group having a carbon number of a to b,
The notation of Ca—Cb cycloalkyl group represents a cyclic saturated hydrocarbon group having a to b carbon atoms.

In the present specification, the expression “which may have one or more atoms or groups selected from group X” means that when it has two or more atoms or groups selected from group X, those The atoms or groups selected from group X may be the same as or different from each other.
In the present specification, the expression “which may have one or more atoms or groups selected from group W” has two or more atoms or groups selected from group W. The atoms or groups selected from group W may be the same as or different from each other.
In the present specification, the expression “may have one or more halogen atoms” means that when two or more halogen atoms are present, the halogen atoms may be the same as or different from each other. May be.

In this compound, “halogen atom” means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

In the present compound, the notation of “C1-C6 alkyl group optionally having one or more atoms or groups selected from group X” refers to a hydrogen atom bonded to a carbon atom depending on an atom or group selected from group X. An optionally substituted linear or branched saturated hydrocarbon group having 1 to 6 carbon atoms, and having two or more atoms or groups selected from group X The atoms or groups selected from the group X may be the same as or different from each other.
Examples of the “C1-C6 alkyl group optionally having one or more atoms or groups selected from group X” include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec- Butyl, tert-butyl, pentyl, neopentyl, hexyl, methoxymethyl, ethoxymethyl, propyloxymethyl, isopropyloxymethyl, butyloxymethyl, sec-butyloxymethyl, tert- Butyloxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-propyloxyethyl group, 2-isopropyloxyethyl group, 2-butyloxyethyl group, 2-sec-butyloxyethyl group, 2-tert -Butyloxyethyl group, trifluoromethyl group, trichloromethyl group, 2-fluoro Oroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group and pentafluoroethyl group, 2-hydroxyethyl group, cyclopropylmethyl group, 1-methylcyclopropylmethyl group, 2,2- C1-C6 alkyl group which may have one or more atoms or groups selected from group X such as difluorocyclopropylmethyl group, trimethoxymethyl group, triethoxymethyl group, etc. It is selected in the range of the number of atoms.

In the present compound, the notation of “C1-C6 alkyl group optionally having one or more halogen atoms” means that a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom and the number of carbon atoms is 1 to Represents a straight-chain or branched-chain hydrocarbon group consisting of six, and in this case, when having two or more halogen atoms, these halogen atoms may be the same or different from each other Good.
Examples of the “C1-C6 alkyl group optionally having one or more halogen atoms” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Group, pentyl group, neopentyl group, hexyl group, trifluoromethyl group, trichloromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group and pentafluoroethyl group, Examples thereof include C1-C6 alkyl groups which may have one or more halogen atoms such as heptafluoroisopropyl group, and each is selected within the range of the designated number of carbon atoms.

In the present compound, examples of the “C1-C6 alkyl group optionally having one or more atoms or groups selected from group W” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group. , Sec-butyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, trifluoromethyl group, trichloromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-tri Fluoroethyl group, pentafluoroethyl group, methoxymethyl group, ethoxymethyl group, propyloxymethyl group, isopropyloxymethyl group, butyloxymethyl group, sec-butyloxymethyl group, isobutyloxymethyl group, tert-butyloxymethyl group , Methoxyethyl group, ethoxyethyl group, propyloxye Having one or more atoms or groups selected from the group W such as a thiol group, isopropyloxyethyl group, butyloxyethyl group, sec-butyloxyethyl group, isobutyloxyethyl group, tert-butyloxyethyl group, etc. C2-C6 alkyl group may be mentioned. At this time, when it has two or more atoms or groups selected from the group W, the atoms or groups selected from the group W may be the same as or different from each other.

In this compound, examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” include methoxy group, trifluoromethoxy group, ethoxy group, 2,2,2-trifluoroethoxy group, propyl group Examples thereof include an oxy group, isopropyloxy group, butyloxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, pentyloxy group and hexyloxy group.

In the present compound, examples of the “C3-C6 cycloalkyl group optionally having one or more halogen atoms” include a cyclopropyl group, a 2,2-difluorocyclopropyl group, a 2,2-dichlorocyclopropyl group, Examples include 2,2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group.

In this compound, examples of the “C3-C6 cycloalkyl group optionally having one or more halogen atoms or one or more C1-C3 alkyl groups” include a cyclopropyl group, a 1-methylcyclopropyl group, 2 -Methylcyclopropyl group, 1-fluorocyclopropyl group, 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group It is done.

In this compound, the expression “C1-C3 haloalkyl group” refers to a linear or branched chain having 1 to 3 carbon atoms in which one or more hydrogen atoms bonded to carbon atoms are substituted with halogen atoms. Represents a hydrocarbon group, and when it has two or more halogen atoms, these halogen atoms may be the same as or different from each other.
Examples of the “C1-C3 haloalkyl group” include a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, and trichloromethyl. Group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, heptafluoropropyl group and heptafluoroisopropyl Groups and the like.

In the present compound, examples of the “C1-C3 alkyl group” include a methyl group, an ethyl group, a propyl group, and an isopropyl group.

In the present compound, examples of the “C1-C3 perfluoroalkyl group” include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a heptafluoroisopropyl group.

Examples of the present compound include compounds represented by the formula (1) shown in the following [Table 1] to [Table 20].

　

　　　　　　　

　
　

Here, the description of “*” in the present compounds in the above Tables [Table 1] to [Table 20] means N-oxide. Specifically, it is the following compound.

Compound 22 Compound 36 Compound 37

Compound 47 Compound 48 Compound 51

The present compound 70 The present compound 400 The present compound 401

Compound 409 Compound 410

This compound 456 This compound 457 This compound 458

This compound 459 This compound 460 This compound 461

In the above [Table 1] to [Table 20], Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, Bu represents a butyl group, tBu represents a tertiary butyl group, iPr represents an isopropyl group, CycPr represents a cyclopropyl group, and CycBu represents a cyclobutyl group.

These compounds can be produced by a method described in International Publication No. 2013/018928 or International Publication No. 2014/104407. For some compounds, the production methods are described below.

Production Example 1 (1)
2- (3-Ethylsulfanyl-pyridin-2-yl) -6-iodo-3-methyl-3H-imidazo [4,5-b] pyridine 1.1 g, copper iodide 160 mg, sodium sulfide nonahydrate 2 A mixture of 0.7 g and 10 mL of N, N-dimethylformamide (hereinafter referred to as DMF) was stirred at 110 ° C. for 5 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

710 mg of the compound represented by the following (hereinafter referred to as compound (1-1)) was obtained.
¹ H-NMR (DMSO-D ₆ ) δ: 8.56-8.55 (2H, m), 8.53-8.50 (2H, m), 8.38-8.36 (2H, m) , 8.04 (2H, d), 7.61-7.56 (2H, m), 3.87 (6H, brs), 3.00 (4H, q), 1.23-1.16 (6H) , M).

Production Example 1 (2)
A mixture of 710 mg of compound (1-1) and 12 mL of DMF was cooled to −60 ° C., and 10 g of trifluoroiodomethane was added. To this mixture, 1.2 mL of tetrakis (dimethylamino) ethylene was added dropwise at −40 ° C. The temperature was raised to −10 ° C., and the mixture was stirred at −10 ° C. for 5 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 2- (3-ethylsulfanyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine (hereinafter, This is referred to as the present compound 13.) 530 mg was obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.67 (1H, d), 8.52 (1H, dd), 8.46 (1H, d), 7.79 (1H, dd), 7.39 ( 1H, dd), 4.03 (3H, s), 2.97 (2H, q), 1.36 (3H, t).

Production Example 2
A mixture of this compound 13 (200 mg), m-chloroperbenzoic acid (purity 65% or more) 230 mg, and chloroform 10 mL was stirred for 5 hours under ice cooling. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfinyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine (hereinafter, This compound is referred to as compound 14.) 89 mg and 2- (3-ethylsulfonyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present compound) It is described as Compound 15.) 130 mg was obtained.
Compound 14

¹ H-NMR (CDCl ₃ ) δ: 8.87-8.83 (1H, m), 8.73-8.64 (2H, m), 8.41 (1H, d), 7.72-7 .66 (1H, m), 4.34 (3H, s), 3.72-3.62 (1H, m), 3.17-3.05 (1H, m), 1.47 (3H, t ).
Compound 15

¹ H-NMR (CDCl ₃ ) δ: 9.01-8.98 (1H, m), 8.71 (1H, d), 8.55-8.52 (1H, m), 8.39 (1H , D), 7.72 (1H, dd), 3.90-3.81 (5H, m), 1.36 (3H, t).

Production Example 3 (1)
To a mixture of 1.39 g of 3-chloro-2-cyanopyridine, 0.9 ml of ethyl mercaptan and 10 ml of DMF, 0.52 g of sodium hydride (60%, oily) was added under ice cooling, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.52 g of 2-cyano-3-ethylsulfanylpyridine.

¹ H-NMR (CDCl ₃ ) δ: 8.49 (1H, dd), 7.75 (1H, dd), 7.43 (1H, dd), 3.06 (2H, q), 1.38 ( 3H, t).

Production Example 3 (2)
To a mixture of 15 ml of concentrated sulfuric acid and 5 ml of water, 1.4 g of 2-cyano-3-ethylsulfanylpyridine was added and stirred at 130 ° C. for 2 hours. To the reaction mixture allowed to cool to room temperature, an aqueous potassium hydroxide solution was added, and the mixture was extracted with ethyl acetate. Concentrated hydrochloric acid was added to the resulting aqueous layer, and the mixture was extracted with chloroform, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 1.15 g of 3-ethylsulfanylpicolinic acid.

¹ H-NMR (CDCl ₃ ) δ: 8.31 (1H, d), 7.75 (1H, d), 7.49 (1H, dd), 2.97 (2H, q), 1.44 ( 3H, t).

Production Example 3 (3)
1.0 g of 2-amino-4- (trifluoromethylsulfanyl) phenol (synthesized by the method described in WO2009 / 131237), 0.87 g of 3-ethylsulfanylpicolinic acid, 1-ethyl-3- (3 A mixture of 1.10 g of (dimethylaminopropyl) carbodiimide hydrochloride and 10 ml of chloroform was stirred for 30 minutes at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 1.32 g of 3-ethylsulfanyl-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] picolinamide (hereinafter referred to as compound 3-3) Got.
Compound 3-3

¹ H-NMR (CDCl ₃ ) δ: 10.40 (1H, brs), 9.63 (1H, s), 8.36 (1H, dd), 7.75 (1H, dd), 7.53 ( 1H, d), 7.45 (1H, dd), 7.41 (1H, dd), 7.08 (1H, d), 2.97 (2H, q), 1.44 (3H, t).

Production Example 3 (4)
A mixture of 1.23 g of compound 3-3, 1.28 g of di-2-methoxyethyl azodicarboxylate, 1.39 g of triphenylphosphine and 30 ml of tetrahydrofuran was stirred at room temperature for 1 hour and at 50 ° C. for 1 hour. The reaction mixture allowed to cool to room temperature was concentrated under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.21 g of 2- (3-ethylsulfanylpyridin-2-yl) -5- (trifluoromethylsulfanyl) benzoxazole (hereinafter referred to as the present compound 441). Obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.59 (1H, dd), 8.27 (1H, s), 7.78 (1H, dd), 7.75-7.69 (2H, m), 7.42 (1H, dd), 3.07 (2H, q), 1.47 (3H, t).

Production Example 4
1.47 g of m-chloroperbenzoic acid (purity 65% or more) was added to a mixture of this compound 441 (1.06 g) and 30 ml of chloroform under ice cooling, and the mixture was stirred at room temperature for 6 hours. A 10% aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 0.87 g of 2- (3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethylsulfanyl) benzoxazole (hereinafter referred to as the present compound 443) and 0.17 g of 2- (3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethylsulfinyl) benzoxazole (hereinafter referred to as the present compound 444) was obtained.
Compound 443

¹ H-NMR (CDCl ₃ ) δ: 9.03 (1H, dd), 8.60 (1H, dd), 8.19 (1H, d), 7.80-7.71 (3H, m), 4.02 (2H, q), 1.43 (3H, t).
Compound 444

¹ H-NMR (CDCl ₃ ) δ: 9.04 (1H, dd), 8.61 (1H, dd), 8.35 (1H, d), 7.96-7.86 (2H, m), 7.77 (1H, dd), 4.01 (2H, q), 1.44 (3H, t).

Production Example 5
To a mixture of 0.35 g of this compound 443 and 8 ml of chloroform, 0.43 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice-cooling, followed by stirring at 40 ° C. for 6 hours. A 10% aqueous sodium sulfite solution was added to the reaction mixture allowed to cool to room temperature, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the obtained residue were added 4 ml of acetonitrile, 30 mg of sodium tungstate dihydrate and 4 ml of aqueous hydrogen peroxide (30%), and the mixture was stirred at 80 ° C. for 6 hours. Water was added to the reaction mixture allowed to cool to room temperature, the precipitated solid was collected by filtration, 10% aqueous sodium sulfite solution was added to the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.35 g of 2- (3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethylsulfonyl) benzoxazole (hereinafter referred to as the present compound 445).
Compound 445

¹ H-NMR (CDCl ₃ ) δ: 9.05 (1H, dd), 8.61 (1H, dd), 8.59 (1H, d), 8.17 (1H, dd), 7.96 ( 1H, d), 7.80 (1H, dd), 3.98 (2H, q), 1.45 (3H, t).

Triflumezopyrine used in the present invention is a mesoionic inner salt and is represented by six structural formulas as shown in the following formula (2A).

Triflumezopyrine can be produced by a method described in International Publication No. 2012/092115. In this document, 2-hydroxy-4-oxo-1- (5-pyrimidinylmethyl) -3- [ It is described as 3- (trifluoromethyl) phenyl] -4H-pyrido [1,2-a] pyrimidinium inner salt.

Examples of the aspect of the composition of the present invention include the following.

In formula (1), A ¹ is —NMe—, an oxygen atom or a sulfur atom, A ² is ═N—, ═N (→ O) — or ═CH—, and R ¹ is one or more halogen atoms A C1-C6 alkyl group optionally having atoms, R ² and R ⁴ are hydrogen atoms, and R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms or hydrogen An atom, R ⁵ is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR ¹⁰ , or —S (O) _m R ¹⁰ , and R ⁶ is —NR ¹⁰ R ¹¹ Or a pest control composition comprising a compound which is a hydrogen atom and R ¹⁰ and R ¹¹ are each independently a C1-C3 alkyl group optionally having one or more halogen atoms, and triflumezopyrine object.

In Formula (1), A ¹ is —NMe— or an oxygen atom, A ² is ═N—, ═N (→ O) — or ═CH—, and R ¹ represents one or more halogen atoms. An optionally substituted C1-C6 alkyl group, R ² and R ⁴ are hydrogen atoms, and R ³ is an optionally substituted C1-C3 alkyl group or hydrogen atom. R ⁵ is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR ¹⁰ , or —S (O) _m R ¹⁰ , and R ⁶ is —NR ¹⁰ R ¹¹ or hydrogen. A pest control composition comprising a compound which is an atom and each of R ¹⁰ and R ¹¹ is independently a C1-C3 alkyl group optionally having one or more halogen atoms, and triflumezopyrine.

In Formula (1), A ¹ is —NMe— or an oxygen atom, A ² is ═N—, ═N (→ O) — or ═CH—, and R ¹ is a C1-C6 alkyl group. , R ² , R ⁴ and R ⁶ are hydrogen atoms, R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms or a hydrogen atom, and R ⁵ is one or more halogen atoms. A C1-C3 alkyl group which may have an atom, —OR ¹⁰ , or —S (O) _m R ¹⁰ , wherein R ¹⁰ may have one or more halogen atoms A pest control composition comprising a compound as a group and triflumezopyrine.

In Formula (1), A ¹ is —NMe—, A ² is ═N—, or ═N (→ O) —, R ¹ is a C1-C6 alkyl group, R ² , R ⁴ and R ⁶ is a hydrogen atom, R ³ is a C1-C3 alkyl group which may have one or more halogen atoms or a hydrogen atom, and R ⁵ may have one or more halogen atoms. A compound having a good C1-C3 alkyl group or —S (O) _m R ¹⁰ , wherein R ¹⁰ is a C1-C3 alkyl group optionally having one or more halogen atoms, and triflumezopyrine A pest control composition to contain.

In the formula (1), A ¹ is an oxygen atom, A ² is ═N—, ═N (→ O) — or ═CH—, R ¹ is a C1-C6 alkyl group, R ² , R ⁴ and R ⁶ are hydrogen atoms, R ³ is a C1-C3 alkyl group which may have one or more halogen atoms or a hydrogen atom, and R ⁵ has one or more halogen atoms. An optionally substituted C1-C3 alkyl group, —OR ¹⁰ , or —S (O) _m R ¹⁰ , wherein R ¹⁰ is a C1-C3 alkyl group optionally having one or more halogen atoms; And a pest control composition containing triflumezopyrine.

In Formula (1), A ¹ is an oxygen atom, A ² is ═N—, or ═N (→ O) —, and R ¹ may have one or more halogen atoms. A C6 alkyl group, R ² , R ³ , R ⁴ and R ⁶ are hydrogen atoms, and R ⁵ may be a C1-C3 alkyl group optionally having one or more halogen atoms, or —S (O ) A pest control composition comprising _m R ¹⁰ and a compound in which R ¹⁰ is a C1-C3 alkyl group optionally having one or more halogen atoms, and triflumezopyrine.

In formula (1), A ¹ is an oxygen atom, A ² is ═N—, R ¹ is a C1-C6 alkyl group, and R ² , R ³ , R ⁴ and R ⁶ are hydrogen atoms. R ⁵ is a C1-C3 alkyl group which may have one or more halogen atoms, or —S (O) _m R ¹⁰ , and R ¹⁰ may have one or more halogen atoms. A pest control composition comprising a compound having a good C1-C3 alkyl group and triflumezopyrine.

In formula (1), A ¹ is an oxygen atom, A ² is ═CH—, R ¹ is a C1-C6 alkyl group optionally having one or more halogen atoms, R ² , R ³ , R ⁴ and R ⁶ are a hydrogen atom, and R ⁵ is a C1-C3 alkyl group optionally having one or more halogen atoms, or —S (O) _m R ¹⁰ , and R ¹⁰ A pest control composition comprising a compound wherein C1 is a C1-C3 alkyl group optionally having one or more halogen atoms and trifluoromesopyrine.

In the formula (1), A ¹ is an oxygen atom, A ² is ═CH—, R ¹ is a C1-C6 alkyl group, R ² , R ³ , R ⁴ and R ⁶ are hydrogen atoms. R ⁵ is a C1-C3 alkyl group which may have one or more halogen atoms, or —S (O) _m R ¹⁰ , and R ¹⁰ may have one or more halogen atoms. A pest control composition comprising a compound having a good C1-C3 alkyl group and triflumezopyrine.

In the formula (1), R ¹ may have one or more atoms or groups selected from group Y (group Y: may have one or more halogen atoms). A group consisting of a C3-C6 cycloalkyl group and a halogen atom)), R ² and R ⁴ are hydrogen atoms, and R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ may have one or more halogen atoms, a C1-C3 alkyl group, —OR ¹⁰ , —S (O) _m R ¹⁰ , —CO ₂ R ¹⁰ , —SF ₅ or a halogen atom, and R ⁶ is —OR ¹⁰ , —NR ¹⁰ R ¹¹ , —CO ₂ R ¹⁰ , —C (O) NR ¹⁰ R ¹¹ , —OC (O) R ^10, a cyano group, Oh halogen atom or a hydrogen atom , ^{R 7} is one or more halogen atoms optionally may C1-C6 alkyl group optionally having _{a ^{-CH 2 CO 2 R 10, C3}} -C6 cycloalkyl group or a hydrogen atom, ^{R 8} is 1 or more A C1-C3 alkyl group optionally having a halogen atom, —OR ¹⁰ , —S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ¹⁰ and R ¹¹ are each independently 1 A C1-C3 alkyl group or a hydrogen atom which may have the above halogen atoms (provided that in -S (O) _m R ¹⁰ , when m is 1 or 2, R ¹⁰ represents a hydrogen atom) A pest control composition comprising a compound which is) and triflumezopyrine.

In formula (1), R ¹ is a C1-C3 alkyl group which may have one or more halogen atoms, R ² and R ⁴ are hydrogen atoms, and R ³ is one or more halogen atoms. A C1-C3 alkyl group optionally having —, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ being a C1-C3 alkyl group optionally having one or more halogen atoms , —OR ¹⁰ , —S (O) _m R ¹⁰ or a halogen atom, R ⁶ is a cyano group, —NR ¹⁰ R ¹¹ , a halogen atom or a hydrogen atom, and R ⁷ has one or more halogen atoms. An optionally substituted C1-C6 alkyl group, R ⁸ is —S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ¹⁰ and R ¹¹ are independently one or more halogen atoms. C1-C3 al optionally having an atom A compound which is a group, pesticidal composition containing the tri full meso pilin.

In formula (1), R ¹ is an ethyl group, R ² and R ⁴ are hydrogen atoms, and R ³ may be a C1-C3 alkyl group optionally having one or more halogen atoms, —C ( OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom,
R ⁵ is a C1-C3 haloalkyl group, —OR ²⁰ , —S (O) _m R ²⁰ or a halogen atom (R ²⁰ represents a C1-C3 haloalkyl group), R ⁶ is a cyano group, —NR ¹⁰ R ¹¹ Are a halogen atom or a hydrogen atom, R ⁷ is a C1-C6 alkyl group optionally having one or more halogen atoms, R ⁸ is —S (O) _m R ¹⁰ , a cyano group, a halogen atom Or a pest control composition comprising a compound which is a hydrogen atom, and R ¹⁰ and R ¹¹ are each independently a C1-C3 alkyl group optionally having one or more halogen atoms, and triflumezopyrine .

A pest control composition comprising a compound of the formula (1) wherein A ¹ is —NR ⁷ — and triflumezopyrine.

A pest control composition comprising a compound wherein A ¹ is an oxygen atom in formula (1) and triflumezopyrine.

In Formula (1), A ¹ is —NR ⁷ —, R ¹ is a C1-C3 alkyl group, R ² and R ⁴ are hydrogen atoms, and R ³ has one or more halogen atoms. An optionally substituted C1-C3 alkyl group, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ is a C1-C3 haloalkyl group, —OR ²⁰ , —S (O) _m R ²⁰ or a halogen atom R ⁶ is a cyano group, —NR ¹⁰ R ¹¹ , a halogen atom or a hydrogen atom, R ⁷ is a C1-C6 alkyl group optionally having one or more halogen atoms, and R ⁸ is -S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ¹⁰ and R ¹¹ are each independently a C1-C3 alkyl group optionally having one or more halogen atoms, R ²⁰ is a C1-C3 haloalkyl group And a pest control composition comprising triflumezopyrine.

In Formula (1), A ¹ is an oxygen atom, R ¹ is an ethyl group, R ² , R ⁴ and R ⁶ are hydrogen atoms, and R ³ has one or more halogen atoms. A C1-C3 alkyl group, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ is a C1-C3 haloalkyl group, —OR ²⁰ , —S (O) _m R ²⁰ or a halogen atom. , R ⁸ is —S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, R ¹⁰ is a C1-C3 alkyl group optionally having one or more halogen atoms, and R ²⁰ A pest control composition comprising a compound wherein is a C1-C3 haloalkyl group and triflumezopyrine.

In Formula (1), A ¹ is an oxygen atom, R ¹ is an ethyl group, R ² , R ^4, and R ⁶ are hydrogen atoms, R ³ is a halogen atom or a hydrogen atom, and R ⁵ is A compound having a C1-C3 perfluoroalkyl group, —OR ³⁰ or —S (O) _m R ³⁰ , R ³⁰ is a C1-C3 perfluoroalkyl group, and R ⁸ is a halogen atom or a hydrogen atom; A pest control composition containing mesopilin.

The composition of the present invention may be a mixture of the present compound and triflumezopyrine, but usually, the present compound, triflumezopyrine and an inert carrier are mixed, and if necessary, a surfactant or other Addition of adjuvants for preparations and preparations formulated into oils, emulsions, flowables, wettable powders, granular wettable powders, powders, granules and the like are used.
The formulated pest control composition can be used as it is or with other inactive ingredients added.
The total amount of the present compound and triflumezopyrine in the composition of the present invention is usually in the range of 0.1% to 100% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80% by weight.

Examples of the inert carrier used for formulation include a solid carrier and a liquid carrier. Examples of such solid carriers include clays (kaolin clay, diatomite, bentonite, fusami clay, acid clay), synthetic hydrous silicon oxide, talc, ceramic, and other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, Hydrated silica, etc.), fine powders and granules of chemical fertilizers (ammonium sulfate, phosphorous, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, etc.) Resin, nylon resin such as nylon-6, nylon-11, nylon-66, polyamide resin, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer).

Examples of such liquid carriers 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 carbonization, and the like. Hydrogen (toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), 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, Butyronitrile, etc.), 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 (Soybean oil, cottonseed oil, etc.).

Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyethylene glycol fatty acid ester, and the like, and alkyl sulfonates, alkyl benzene sulfonates, alkyl sulfates, and the like. An ionic surfactant is mentioned.

Other formulation adjuvants include sticking agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), bentonite, synthetic water-soluble Polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4 -Methoxyphenol and 3-tert-butyl-4-methoxyphenol).

The pest control method of the present invention is carried out by applying an effective amount of the composition of the present invention to pests or pest habitats (plants, soil, etc.). The pest control method of the present invention is usually used in the form of a pest control agent in which the composition of the present invention is formulated.

Specifically, the application method of the composition of the present invention includes, for example, application to plant stems and leaves, flower vases, seedlings or ears (plants), soil before planting or after planting (cultivate plants) Application to soil), seed disinfection, seed soaking, application to plant seeds such as seed coats or bulbs such as seed pods. In addition, this compound and triflumezopyrine may be applied separately, and seeds or bulbs to which either this compound or triflumezopyrine is attached are applied to plants, plant seeds, bulbs or soil where plants are grown. The remaining one may be applied before and after.

As application to the foliage, flower vase, seedling or ear (plant) of the plant, specifically, application methods applied to the surface of the plant such as foliage spray, trunk spray, etc., and before flowering, during flowering, Examples include a method of spraying the entire vase or the whole plant at the flowering time including after flowering, and a method of spraying the head or the whole plant at the heading time for cereals.

In addition, the application method to the soil before planting or after planting (soil for cultivating plants) is, for example, the composition of the present invention in the rhizosphere of a crop to be protected from damage such as feeding by pests. It is a method for directly controlling pests by applying a product, or a method for controlling pests that feed plants by osmotically transferring the composition of the present invention from the root or the like into the plant body.
Specifically, for example, planting treatment (planting hole spraying, planting hole treatment soil mixing), plant source processing (stock source spraying, strain source soil mixing, strain source irrigation, late seedling stage plant source processing), planting groove processing (Groove spraying, grooving soil admixture), cropping treatment (growing sprinkling, cropping soil blending, growing season cropping spraying), sowing cropping treatment (sowing cropping spraying, sowing cropping soil blending) , Whole surface treatment (overall soil spraying, whole surface soil mixing), side strip treatment, water surface treatment (water surface application, water surface application after flooding), other soil spraying treatment (growth season foliar leaf surface spraying, under the crown or around the trunk, Soil surface spraying, soil surface mixing, sowing hole spraying, buttocks ground surface spraying, inter-strain spraying), and other irrigation treatments (soil irrigation, seedling irrigation, chemical solution injection treatment, local irrigation, chemical drip irrigation, chemical ligation), Nursery box processing (nursery box spraying, seedling box irrigation, seedling box chemical solution watering), seedling tray processing Nursery tray spraying, seedling tray irrigation, seedling tray chemical solution flooding), nursery treatment (seedbed spraying, nursery bed irrigation, water seedling surrogate nursery spraying, seedling immersion), floor soil mixing treatment (floor soil mixing, bed soil mixing before sowing, seeding) Application before soil covering, after soil covering after seeding, mixing with soil covering) and other treatments (mixing soil, mixing, topsoil mixing, rain soil mixing, planting position treatment, granule inflorescence spraying, paste fertilizer mixing).

Application to plant seeds or bulbs can also be carried out by applying the composition of the present invention to plant seeds or bulbs. In the present invention, the plant seed means the seed of the plant in a state before being sown in the soil or the culture medium, and the bulb is a bulb, a bulb of the plant in a state before being planted in the soil or the culture medium. It means tubers, rhizomes, stem fragments, seed pods and tuberous roots. The method of applying the composition of the present invention to plant seeds or bulbs is, for example, a method of controlling pests by directly applying to plant seeds or bulbs of crops to be protected from damage such as feeding by pests; A method for controlling pests that feed on seeds or the like by applying the composition of the present invention in the vicinity of seeds or bulbs; or by osmotically transferring the composition of the present invention from plant seeds or bulbs into the plant body This is a method for controlling pests that feed plants, and specific examples include spraying, smearing, dipping, impregnation, coating, film coating, and pellet coating. .

When the composition of the present invention is used for pest control, the application amount can vary widely depending on the application time, application location, application method, etc., but in general, the present compound and triflumezopyrine The total amount of is usually 1 to 10,000 g per 10,000 m ² . When the composition of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., the present compound and triflumezopyrine are usually adjusted so that the total concentration thereof is 0.01 to 10,000 ppm. It is diluted with water and applied, and granules, powders and the like are usually applied as they are.

Also, when the composition of the present invention is applied to rice, it may be used in a seedling box treatment. The time for treating the seedling box of the composition of the present invention may be from the time of sowing rice to the time of transplanting. The composition of the present invention may be used in direct seeding or transplantation cultivation of rice. When the composition of the present invention is used for direct sowing cultivation rice, it may be applied before direct sowing, after direct sowing, before direct sowing or after direct sowing, and from before sowing to 21 days after sowing. Also good. When the composition of the present invention is used for transplanted rice, it may be rice after transplanting, and the time of application may be from before transplanting to 21 days after transplanting.

The pests for which the composition of the present invention is effective include harmful arthropods such as harmful insects and harmful ticks, and specific examples of such pests include the following.

Hemiptera: small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), planthoppers such as Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), tea Roh green leafhopper (Empoasca onukii) such as Leafhoppers, cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), radish aphids (Brevicorine brassicae), aphid spiraecola, tulip beetle aphids Macrosiphum euphorbiae, potato beetle aphids (Aulacorthum solani), wheat beetle aphids (Rhopalosiphum aphids), citrus aphids (Toxoptera citricidus), peach beetles Stink bugs such as stink bugs (Riptortus clavetus), spider helicopter bugs (Leptocorisa chinensis), bark beetle bugs (Eysarcoris parvus), wing beetle bugs (Halyomorpha mista) es vaporariorum), sweetpotato whitefly (Bemisia tabaci), mandarin orange whitefly (Dialeurodes citri), whiteflies such as mandarin orange spiny whitefly (Aleurocanthus spiniferus).

Lepidoptera: rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Japanese medusa such as Shibata toga (Pediasia teterrellus), Spodoptera litura, Spodoptera exigua, Ayuyotoga (Pseudaletia sepata), Atoga assicae), Agrotis ipsilon, Tamanaginawaba (Plusia nigrisigna), Trichopulsia, Heliotis, Helicoberpa, etc. , Atsukiyamamushiga (Matsumuraeses azukivivora), Apple wolfberry (Adoxophyes orana fascita), Chanokokumonmonami (Adoxophyces honmai), Chamonamaki (Homomonakimaki) Upperus, Cyperpomonella, and other species, Caloptilia theivoria, Phyllonarycter lingoneis, etc. Species of the genus Kutis, Suga such as Plutella xylostella, Cotton worm (Pectinophora)
gossypiella potatoes (Phythromea operculella) and other yellow moths, Hyphantoria cunea and other tigers, and iga (Tinea translucens).

Thrips of the order Thrips thrips (Franklinella occidentalis), Thrips palmi, etc.

Diptera: insect fly (Delia platera), onion fly (Delia antiqua), etc.
trifoliii), leafworms such as Chlamatomyia horticola, leafworms such as Chlorops oryzae, fruit fly of Dacus cucurbita

Coleoptera pests: Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Weevil (Sitophilus zeamais), Rice weevil (Lissohoptrus oryzophilus), Bone weevil (Echinocnemus squameus), Cotton weevil (Anthonomus grandis) nophorus venatus) weevils such as, Chai loco Meno mealworm (Tenebrio molitor), red flour beetle (Tribolium castaneum) Tenebrionidae such as, Inedorooimushi (Oulema oryzae), cucurbit leaf beetle (Aulacophora femoralis), Kisujinomihamushi (Phyllotreta striolata), Colorado potato beetle (Leptinotarsa potato beetles such as decemlineata, epilacunas such as Epilachna vigintioctopuncta, Lyctus brunneus, pine wood beetle (Tomicus piniperk), etc. Insects, Naga Shinkuimushi acids, Hyouhonmushi acids, Gomadarakamikiri (Anoplophora malasiaca) beetles such as, click beetles such (Agriotes spp., Limonius spp.), And Aoba ants backlash Staphylinidae (Paederus fuscipes).

The above-mentioned pests include populations that have acquired resistance to existing agents, and the composition of the present invention is also effective against such resistant populations.

As a plant which can use this invention composition, the following are mentioned, for example.
Agricultural crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, oilseed rape, sunflower, sugarcane, tobacco, etc., vegetables: solanaceous vegetables (eggplants, tomatoes, peppers, peppers, Potato, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, squash, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (Burdock, shungiku, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), sericaceae vegetables (carrot, parsley, celery, American burdock etc.), red crustacean vegetables (spinach, chard, etc.), Lamiaceae vegetables (Perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
Bridegroom,
Foliage plant,
Shiva,
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, etc.
Trees other than fruit trees: Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.

The above-mentioned plant may be a plant bred by hybrid technology.

That is, a plant bred by hybrid technology is a plant having the characteristics of hybrid stress (generally resulting in increased yield potential, improved resistance to biological and abiotic stress factors, etc.).

The above-mentioned plant may be a plant imparted with resistance by genetic recombination technology.

For example, the above-mentioned plants are resistant to HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors, glutamine synthase inhibitors, and herbicides such as bromoxynil and dicamba. However, plants that have been imparted by classical breeding methods or genetic engineering techniques are also included.

The above-mentioned plants include plants that can synthesize, for example, selective toxins known in the genus Bacillus using genetic recombination technology.

In addition, the above-mentioned plants are provided with two or more kinds of traits related to herbicide resistance, pest resistance, disease resistance, etc., as described above, using classical breeding techniques or genetic recombination techniques, and the like Alternatively, a line to which two or more kinds of properties possessed by the parent line are given by crossing genetically modified plants having different characteristics is also included. Examples of such plants include Smart stax (registered trademark).

In the composition of the present invention, the content ratio of the present compound and triflumezopyrine is usually 100: 1 to 1: 100, preferably 10: 1 to 1:10, by weight.

The composition of the present invention may further contain one or more compounds selected from the following group (A).
Group (A):
Clothianidin, dinotefuran, thiamethoxam, imidacloprid, ethenrome, fenroyl, fenroyl ), Chlorantraniliprole, cyantraniliprole, cartap, flupiradifurone, pymetrozine, iso Anil (isotiilil), azoxystrobin (oryastrostrobin), probenazole (probenazole), thiazinyl (tiadinil), tricyclazole (e), ciromone (etrozil) phthalide), kasugamycin hydrochloride, tebufloquin, pencycuron, validamycin, hexaconazole, fluconazolole tolanil, carpropamide, furamethpyr, penflufen, and tolprocarb
The group which consists of a compound shown by these.

Examples of such a combination include the following.
A combination of “any one of Compounds 1 to 481” with triflumezopyrine and isothianyl;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and orisatrobin;
A combination of “any one of Compounds 1 to 481” with triflumezopyrine and probenazole;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and tricyclazole;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and diclosimet;
A combination of “any one of the present compounds 1 to 481”, triflumezopyrine and carpropamide;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and thiazinyl;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and pyrokilone;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and tolprocarb;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and flametopyr;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine and penflufen;

A combination of “any one of the present compounds 1 to 481” with triflumezopyrine, isotianil and flametopyr;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine, isotianil and penflufen;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine, probenazole, and flametopir;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine, probenazole and penflufen;

A combination of “any one of the present compounds 1 to 481” with triflumezopyrine, tricyclazole and flametopyr;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine, tricyclazole and penflufen;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine, thiazinyl and furametopyl;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine, thiazinyl and penflufen;

A combination of “any one of the present compounds 1 to 481” with triflumezopyrine, pyrokilone and flametopyr;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine, pyrokilone and penflufen;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine, toluprocarb and furametopir;
A combination of “any one of the present compounds 1 to 481” with triflumezopyrine, tolprocarb and penflufen;

Hereinafter, the present invention will be described in more detail with formulation examples and test examples, but the present invention is not limited to the following examples. In the following examples, parts represent parts by weight unless otherwise specified.

First, formulation examples are shown.

Formulation Example 1
5 parts of any one of the present compounds 1 to 481, 10 parts of triflumezopyrine, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water are mixed to give a total amount. Each of the preparations is obtained by finely pulverizing with 100 parts by a wet pulverization method.

Formulation Example 2
Any one of the present compounds 1 to 481 was mixed with 10 parts of an aqueous solution containing 10 parts of triflumezopyrine, 1.5 parts of sorbitan trioleate, and 2 parts of polyvinyl alcohol, and pulverized by a wet pulverization method. Thereafter, an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto to make a total amount of 90 parts, and further 10 parts of propylene glycol is added and mixed by stirring to obtain each preparation.

Formulation Example 3
By thoroughly pulverizing and mixing 10 parts of any one of the present compounds 1 to 481, 10 parts of triflumezopyrine, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and the remainder of the synthetic silicon hydroxide, 100 parts of wettable powder are obtained.

Formulation Example 4
1 part of any one of the present compounds 1-481, 0.5 part of triflumezopyrine, 1 part of synthetic silicon hydrous powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and the remainder of kaolin clay are mixed. . Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated with a granulator, and dried by ventilation to obtain 100 parts of each granule.

Formulation Example 5
2 parts of any one of the present compounds 1 to 481, 0.75 parts of triflumezopyrine, 2 parts of isotianil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and the remainder of kaolin clay 100 parts of the mixture is pulverized and mixed well, water is added and kneaded well, and then granulated and dried to obtain 100 parts of granules.

Formulation Examples 6-15
In Formulation Example 5, in place of 2 parts of isotianil, the same operations as in Formulation Example 5 are carried out except that the respective compounds and amounts used described in [Table A] are used to obtain respective granules.

[Table A]

Next, application examples of the composition of the present invention to plant seeds will be shown.
Application example 1
Each treated seed was smeared on 200 kg of each preparation prepared according to Preparation Example 1 or 2 using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH) on 100 kg of dried sorghum seeds. Get.
Alternatively, each treated seed can also be obtained by adding 180 grams of oxabetrinyl or 40 grams of floxophenim to 200 ml of each preparation and applying a smear treatment.

Application example 2
Each dried seed of corn is treated with a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH) by applying 40 ml of each preparation prepared according to Preparation Example 1 or 2, to each treated seed. Get.

Application example 3
Treated seeds are obtained by applying 50 g of each wettable powder prepared according to Formulation Example 3 to 10 kg of dried corn seeds.

Application example 4
Each dried seed is treated with a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH) using 20 ml of each preparation prepared according to Preparation Example 1 or 2, and each treated seed is then smeared. Get.

Application example 5
10 kg of dried soybean seeds were treated with 30 g of each wettable powder prepared according to Formulation Example 3 using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH). Get seeds.

Application Example 6
Each dried seed is treated with a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH) using 50 ml of each formulation prepared according to Formulation Example 1 or 2, and each treated seed is smeared. Get.

Application example 7
By subjecting 10 kg of dried oilseed rape seeds to 150 kg of each of the preparations prepared according to Preparation Example 1 or 2, using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH) Get seeds.

Application example 8
For each 10 kg of dried rice seed, 20 ml of each preparation prepared according to Preparation Example 1 or 2 was smeared using a rotary seed processing machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH). Get seeds.

Application example 9
For each 10 kg of dried rice seeds, 60 g of each wettable powder prepared according to Formulation Example 3 was dressed with a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH). Get seeds.

Next, the effect of the present invention will be shown by test examples.

Test example 1
This compound 3, 15, 19, 20, 48, 50, 72, 81, 85, 99, 130, 421, 444, 445, 464, 467, and triflumezopyrine per mg, xylene: dimethylformamide: surfactant After dissolving using 10 μL of a mixed solvent (trade name: Solpol (registered trademark) 3005X, manufactured by Toho Chemical Co., Ltd.) = 4: 4: 1 (volume ratio), the concentrations described in [Table 21] to [Table 22] Each test chemical solution was prepared by diluting with 0.02% by volume of a spreading agent (trade name: Cindyne (registered trademark), manufactured by Sumitomo Chemical Co., Ltd.).
Cucumber (Cucumis sativus) cotyledon leaf pieces (1.5 cm in length) are housed in each well of a 24-well microplate (Becton Dickinson), 2 cotton aphids (Aphis gossypii) adults and 8 larvae per well Was released and sprayed with 20 μL of the test drug solution per well. This was designated as a treatment zone.
In addition, the well which sprayed 20 microliters of water containing 0.02 volume% of spreading agents (brand name: Cyndine (trademark), Sumitomo Chemical) instead of the chemical | medical solution for a test was made into the no-treatment group.
After air drying, the upper part of the microplate was covered with a gas-permeable film sheet (trade name: AeraSeal, manufactured by Excel Scientific Inc.), and the number of live insects in each well was observed after 5 days of release.
The control value of the treated area and the untreated area was calculated from the following formula (1).
Formula (1) Control value (%) = {1− (Tai) / (Cai)} × 100
In addition, the character in a formula represents the following meaning.
Cai: Number of surviving insects at the time of observation of the untreated group Tai: Number of surviving insects at the time of observation of the treated group As a result, as shown in [Table 21] to [Table 22], the present compounds 3, 15, 19, 20, All of the compositions of the present invention containing 48, 50, 72, 81, 85, 99, 130, 421, 444, 445, 464, or 467 and triflumezopyrine showed excellent control efficacy.
In addition, the control value of triflumezopyrine and the present compound alone observed in a test conducted in accordance with the above-described test is 4 (concentration 0.1 ppm), 30 (concentration 1 ppm), and the present compound 15 Is 28 (concentration 1 ppm), the present compound 20 is 12 (concentration 0.01 ppm), the present compound 72 is 32 (concentration 10 ppm), the present compound 444 is 32 (concentration 1 ppm), and the present compound 445 is 30 (concentration 0.1 ppm) This compound 445 was 37 (concentration 1 ppm).

According to the present invention, pests can be controlled.

Claims (9)

1. Formula (1):
   

   

   [Where:
   A ¹ represents —NR ⁷ —, an oxygen atom or a sulfur atom,
   A ² is = N -, = N (→ O) - , or = CR ⁸ - represents,
   Q represents = N- or = N (→ O)-
   R ¹ represents a C1-C6 alkyl group optionally having one or more atoms or groups selected from group X;
   R ² , R ³ and R ⁴ are the same or different and are a C1-C6 alkyl group optionally having one or more atoms or groups selected from group X, —OR ¹⁰ , —S (O) _m R ¹⁰ , —S (O) ₂ NR ¹⁰ R ¹¹ , —NR ¹⁰ R ¹¹ , —NR ¹⁰ CO ₂ R ¹¹ , —NR ¹⁰ C (O) R ¹¹ , —CO ₂ R ¹⁰ , —C (O) R ¹⁰ , -C (O) NR ¹⁰ R ¹¹ , -SF ₅ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
   R ⁵ and R ⁶ are the same or different and are a C1-C6 alkyl group optionally having one or more atoms or groups selected from Group X, —OR ¹⁰ , —S (O) _m R ¹⁰ , — S (O) ₂ NR ¹⁰ R ¹¹ , —NR ¹⁰ R ¹¹ , —NR ¹⁰ CO ₂ R ¹¹ , —NR ¹⁰ C (O) R ¹¹ , —CO ₂ R ¹⁰ , —C (O) R ¹⁰ , —C (O) NR ¹⁰ R ¹¹ , —OC (O) R ¹⁰ , —SF ₅ , a cyano group, a nitro group, a halogen atom or a hydrogen atom (provided that R ⁵ and R ⁶ do not represent a hydrogen atom at the same time) ),
   R ⁷ is a C1-C6 alkyl group optionally having one or more atoms or groups selected from group W, —CO ₂ R ¹⁰ , —C (O) R ¹⁰ , —CH ₂ CO ₂ R ¹⁰ , Represents a C3-C6 cycloalkyl group or a hydrogen atom,
   R ⁸ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹⁰ , —S (O) _m R ¹⁰ , —NR ¹⁰ R ¹¹ , —CO ₂ R ¹⁰ , —C ( O) represents R ¹⁰ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
   R ¹⁰ and R ¹¹ are the same or different and each represents a C1-C6 alkyl group or a hydrogen atom which may have one or more atoms or groups selected from group X (provided that —S (O) _m R ¹⁰ , when m is 1 or 2, R ¹⁰ does not represent a hydrogen atom)
   m independently represents 0, 1 or 2, and n represents 0, 1 or 2.
   Group X: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 cycloalkyl optionally having one or more halogen atoms or one or more C1-C3 alkyl groups A group consisting of a group, a cyano group, a hydroxy group and a halogen atom.
   Group W: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 cycloalkyl group optionally having one or more halogen atoms, hydroxy group, halogen atom and cyano group A group consisting of And a 2,4-dioxo-1- (5-pyrimidinylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H-pyrido [1,2-a] pyrimidinium inner salt, A pest control composition comprising:
2. A ¹ is -NMe-, an oxygen atom or a sulfur atom,
   A ² is = N-, = N (→ O)-or = CH-,
   R ¹ is a C1-C6 alkyl group optionally having one or more halogen atoms,
   R ² and R ⁴ are hydrogen atoms,
   R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms or a hydrogen atom,
   R ⁵ is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR ¹⁰ , or —S (O) _m R ¹⁰ ;
   R ⁶ is —NR ¹⁰ R ¹¹ or a hydrogen atom,
   R ¹⁰ and R ¹¹ are each independently a C1-C3 alkyl group optionally having one or more halogen atoms.
   The pest control composition according to claim 1.
3. The pest control composition according to claim 1 or 2, wherein A ¹ is -NMe-.
4. Pesticidal composition according to claim 1 or claim 2 A ¹ is an oxygen atom.
5. A compound represented by the formula (1) and a 2,4-dioxo-1- (5-pyrimidinylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H-pyrido [1,2-a] pyrimidinium molecule The pest control composition according to any one of claims 1 to 4, wherein the content ratio with the inner salt is 100: 1 to 1: 100 by weight.
6. A compound represented by the formula (1) and a 2,4-dioxo-1- (5-pyrimidinylmethyl) -3- [3- (trifluoromethyl) phenyl] -2H-pyrido [1,2-a] pyrimidinium molecule The pesticidal composition according to any one of claims 1 to 4, wherein the content ratio with the inner salt is 10: 1 to 1:10 by weight.
7. A method for controlling pests comprising a step of applying an effective amount of the pest control composition according to any one of claims 1 to 6 to pests or habitats of pests.
8. A method for controlling pests, comprising a step of applying an effective amount of the pest control composition according to any one of claims 1 to 6 to a plant, plant seeds, bulbs or soil for cultivating plants.
9. A plant seed or bulb to which an effective amount of the pesticidal composition according to any one of claims 1 to 6 is attached.