JP2007070346A - Anthranylamide-based compound, its production method and pest-controlling agent containing it - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new pest-controlling agent, for example, a pest-controlling agent that can repel various pests rampant in agriculture and gardening and parasitic pests on animals. <P>SOLUTION: The anthranylamide-based compound, its N-oxide or its salt are represented by formula (I): (wherein, A is an alkyl substituted by Y or a carbonyl substituted by D; Q is a 3-pyridyl that may be substituted by R<SP>5</SP>or a 4-pyridyl that may be substituted by R<SP>5</SP>; R<SP>1</SP>is a halogen, an alkyl or the like that may be substituted by X; R<SP>2</SP>and R<SP>5</SP>are each a halogen, an alkyl or the like that may be substituted by X; R<SP>3</SP>and R<SP>4</SP>are each a hydrogen atom or an alkyl; X is a halogen, an alkoxy or the like that may be substituted by a halogen; Y is a 3-4C cycloalkyl or the like; D is an alkenyl or the like; m is an integer of 0 to 4; and n is an integer of 1 to 2). <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

WO 01/70671 discloses anthranilamide compounds having a certain chemical structure. However, no compound having an alkyl substituted with C3-4 cycloalkyl or a carbonyl substituted with D as a substituent corresponding to A in the following formula (I) is described.
WO 03/16284 discloses a compound in which 2-pyridyl or phenyl is substituted at the 1-position of the pyrazole ring, while WO 04/67528 discloses a compound in which 2-pyridyl is substituted at the 1-position of the pyrazole ring. Is disclosed. On the other hand, the chemical structure is different because 3-pyridyl or 4-pyridyl is substituted at the 1-position of the pyrazole ring of the following formula (I).

International Publication WO01 / 70671 International Publication WO03 / 16284 International Publication No. WO04 / 67528

  Many pest control agents have been used for many years, but many have various problems such as insufficient efficacy, pests gaining resistance and their use being restricted. Therefore, development of a new pest control agent with few such disadvantages, for example, a pest control agent capable of controlling various pests that are problematic in the field of agriculture and horticulture and pests parasitic on animals is desired.

The present inventors have made various studies on anthranilamide compounds in order to find better pest control agents. As a result, the present inventors have found that a novel anthranilamido compound has a very high control effect against pests at a low dose, and completed the present invention.
That is, the present invention relates to the formula (I):

(Wherein, A is a carbonyl substituted with alkyl or D-substituted with Y, Q is has been or 4-pyridyl substituted with or 3-pyridyl, or R ⁵ to be substituted with R ^5, R ¹ is halogen, alkyl optionally substituted with X, alkenyl optionally substituted with X, alkynyl optionally substituted with X, hydroxy, alkoxy optionally substituted with X, formyl, substituted with X May be alkylcarbonyl, carboxyl, alkoxycarbonyl optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, alkylsulfonyl optionally substituted with X, X Alkylsulfenyloxy which may be substituted, alkylsulfinyloxy which may be substituted with X, alkyls which may be substituted with X Honiruokishi, substituted amino, alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, halogen optionally substituted alkoxyiminoalkyl, cyano or nitro, each of R ² and R ⁵ are halogen, X Alkyl, optionally substituted with X, alkoxy optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, alkylsulfonyl optionally substituted with X, substituted with X Alkylsulfenyloxy optionally substituted with alkylsulfinyloxy optionally substituted with X, alkylsulfonyloxy optionally substituted with X, amino, alkylamino, dialkylamino, formyl, cyano or nitro, R ³ and R ⁴ each hydrogen atom Is alkyl, X is halogen, alkoxy optionally substituted with halogen, alkylsulfenyl optionally substituted with halogen, alkylsulfinyl optionally substituted with halogen, alkylsulfonyl optionally substituted with halogen, or cyano Y is C3-4 cycloalkyl optionally substituted with at least one substituent selected from the group consisting of halogen, alkyl and haloalkyl; haloalkylsulfenyl; haloalkylsulfinyl or haloalkylsulfonyl; D is substituted with halogen Alkenyl optionally substituted with halogen, alkynyloxy optionally substituted with halogen, alkynyl optionally substituted with halogen or alkynyloxy optionally substituted with halogen, m is an integer of 0 to 4, and n is 1 Is an integer of ~ 2) Anthranilamide compounds, their N- oxides or salts, such as their preparation and pesticides containing them.

  The pest control agent comprising the novel anthranilamido compound of formula (I) as an active ingredient has a very high control effect against pests with a low dose.

The number of substituents Y in the substituent Y in A, the substituent R ⁵ in Q, or the substituent X in R ¹ , R ² or R ⁵ may be 1 or 2 or more. The groups may be the same or different. Moreover, the position of each substituent may be any position.
The number of substituents Y in A is preferably 1. The number of substituents R ^{5 in} Q is desirably 1 to 2.
The number of substitutions of halogen as a substituent in R ¹ , X, Y or D may be 1 or 2 or more, and in the case of 2 or more, each halogen may be the same or different. In addition, each halogen may be substituted at any position.
The number of substitution of halogen, alkyl or haloalkyl which is a substituent of C3-4 cycloalkyl in Y may be 1 or 2 or more, and in the case of 2 or more, each substituent may be the same or different. Moreover, the position of each substituent may be any position. The C3-4 cycloalkyl in Y is preferably unsubstituted, or when it has the aforementioned substituent, the number of substitution is preferably 1-5.

Examples of the halogen in R ¹ , R ² , R ⁵ , X, Y or D or the halogen as a substituent include each atom of fluorine, chlorine, bromine or iodine.
The alkyl or alkyl moiety in A, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X or Y may be either linear or branched, and specific examples thereof include methyl, ethyl, propyl , Isopropyl, butyl, tertiary butyl, pentyl, hexyl, and the like.
The alkenyl or alkenyl moiety in R ¹ or D may be linear or branched, and specific examples thereof include vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3-butadienyl, Examples thereof include C2-6 such as 1-hexenyl.
The alkynyl or alkynyl moiety in R ¹ or D may be linear or branched, and specific examples thereof include those of C 2-6 such as ethynyl, 2-butynyl, 2-pentynyl, 3-hexynyl. Etc.
Specific examples of the C3-4 cycloalkyl or cycloalkyl moiety in Y include cyclopropyl and cyclobutyl, with cyclopropyl being particularly preferred.

  Examples of the salt of the anthranilamide compound of the formula (I) include any agriculturally acceptable salt, for example, alkali metal salts such as sodium salt and potassium salt; magnesium salt and calcium salt Alkaline earth metal salts such as: ammonium salts such as dimethylammonium salts and triethylammonium salts; inorganic acid salts such as hydrochlorides, perchlorates, sulfates and nitrates; such as acetates and methanesulfonates Organic acid salts and the like.

The anthranilamido compound of the formula (I) may have isomers such as optical isomers and geometric isomers, and the present invention includes both isomers and isomer mixtures. The present invention includes various isomers other than those described above within the scope of technical common sense in the technical field. In addition, depending on the type of isomer, the chemical structure may be different from that of the formula (I). However, since those skilled in the art can sufficiently recognize that they are related to isomers, the scope of the present invention It is clear that it is within.
The anthranilamide compound of the above formula (I) or a salt thereof (hereinafter abbreviated as the present compound) can be produced according to the following reactions [A] to [E] and a usual salt production method.

A, Q, R ¹ , R ² , R ³ , R ⁴ , m and n are as described above, and Z is a chlorine atom, —OH or C _1-4 alkoxy.
Reaction [A] can usually be carried out in the presence of a base when Z is a chlorine atom.
Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrides such as sodium hydride and potassium hydride; Trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, N, N-dimethylaniline, N, N-diethylaniline , Tertiary amines such as N-ethyl-N-methylaniline, 1,8-diazabicyclo [5.4.0] -7-undecene, 1,4-diazabicyclo [2.2.2] octane; -From alkyl lithiums such as butyl lithium and tert-butyl lithium It can be appropriately selected species or two or more. The base can be used in an amount of 1 to 5 moles, preferably 1 to 2.5 moles based on the compound of the formula (II).

The reaction [A] can be carried out in the presence of a solvent, if desired, when Z is a chlorine atom. Any solvent may be used as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, and dimethoxyethane; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, four Halogenated hydrocarbons such as carbon chloride, dichloroethane, trichloroethane and dichloroethylene; aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; acetonitrile Polar propylene such as propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, N, N-dimethylacetamide, N-methylpyrrolidone Ton solvents; methyl acetate, ethyl acetate, esters such as propyl acetate; acetone, diethyl ketone, methyl ethyl ketone, can be appropriately selected one or more kinds of such ketones such as methyl isobutyl ketone.
When Z is a chlorine atom, the reaction [A] can usually be carried out at -20 to + 60 ° C, preferably 0 to 30 ° C, and the reaction time is usually about 1 to 24 hours, preferably 2 to 12 hours. It can be about hours.

Reaction [A] can usually be carried out in the presence of a dehydrating condensing agent and a solvent when Z is —OH.
Examples of the dehydrating condensing agent include carbodiimides such as N, N′-dicyclohexylcarbodiimide, 1,3-diisopropylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride; -Carbonyl-bis-1H-imidazole, phosphoric acid dichloride phenyl ester, diethyl phosphorocyanidate, 1,3,5-triaza-2,4,6-triphosphorin-2,2,4,4,6,6-hexa Examples include chloride, cyanuric chloride, isobutyl chloroformate, chlorosulfonyl isocyanate, and trifluoroacetic anhydride.

Any solvent may be used as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, and dimethoxyethane; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, four Halogenated hydrocarbons such as carbon chloride, dichloroethane, trichloroethane and dichloroethylene; aromatic hydrocarbons such as benzene, toluene and xylene; acetonitrile, propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphos Polar aprotic solvents such as holic triamide, sulfolane, N, N-dimethylacetamide, N-methylpyrrolidone; esters such as methyl acetate, ethyl acetate, propyl acetate; acetone, Ethyl ketone, methyl ethyl ketone, ketones such as methyl isobutyl ketone; pentane, hexane, heptane, octane, may be appropriately selected aliphatic hydrocarbon such as cyclohexane or the like one or more.
When Z is —OH, the reaction [A] can usually be carried out at −20 to + 60 ° C., preferably 0 to 30 ° C., and the reaction time is usually about 0.5 to 24 hours, preferably 1 It can be about ~ 12 hours.

Reaction [A] can be normally performed in presence of a base and a solvent, when Z is _C1-4 alkoxy.
Bases include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, Pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, N, N-dimethylaniline, N, N-diethylaniline, N-ethyl-N-methylaniline, 1 , 8-diazabicyclo [5.4.0] -7-undecene, one or more selected from tertiary amines such as 1,4-diazabicyclo [2.2.2] octane Can do. The base can be used in an amount of 1 to 5 moles, preferably 1 to 2.5 moles based on the compound of the formula (II).

Any solvent may be used as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, and dimethoxyethane; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, four Halogenated hydrocarbons such as carbon chloride, dichloroethane, trichloroethane and dichloroethylene; aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; acetonitrile Polar propylene such as propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, N, N-dimethylacetamide, N-methylpyrrolidone It can be selected as appropriate one or more of tons of solvent.
When Z is C _1-4 alkoxy, the reaction [A] can usually be carried out at 0 to 120 ° C., preferably 20 to 80 ° C., and the reaction time is usually about 0.5 to 24 hours, preferably Can be about 1 to 12 hours.

A, Q, R ¹ , R ² , R ⁴ , m and n are as described above.
Reaction [B] can be normally performed in presence of a solvent.
Any solvent may be used as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, and dimethoxyethane; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, four Halogenated hydrocarbons such as carbon chloride, dichloroethane, trichloroethane and dichloroethylene; aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; acetonitrile Polar propylene such as propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, N, N-dimethylacetamide, N-methylpyrrolidone It can be selected as appropriate one or more of tons of solvent.

Reaction [B] can be carried out in the presence of a base when A is carbonyl substituted with D. As a base, 1 type (s) or 2 or more types can be suitably selected from alkali metal hydrides, such as sodium hydride and potassium hydride, etc., for example. The base can be used in an amount of 1 to 5 times mol, preferably 1 to 2.5 times mol, of the compound of formula (V).
The reaction [B] can be usually carried out at 0 to 120 ° C., preferably 20 to 80 ° C., and the reaction time is usually about 0.1 to 24 hours, preferably about 0.5 to 12 hours. Can do.

^{A, R 3, R 4,} m and n are as defined above, ^{Q 1} is has been or 4-pyridyl substituted with may also be 3-pyridyl or ^{R 5a} which is substituted with ^{R 5a,} R ^1a is Fluorine atom, chlorine atom, bromine atom, alkyl optionally substituted with X, alkenyl optionally substituted with X, alkynyl optionally substituted with X, hydroxy, alkoxy optionally substituted with X, formyl, X Alkylcarbonyl optionally substituted with carboxyl, alkoxycarbonyl optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, alkyl optionally substituted with X Sulfonyl, alkylsulfenyloxy optionally substituted with X, alkylsulfinyloxy optionally substituted with X, alkyl optionally substituted with X Le sulfonyloxy, amino, alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, optionally substituted by halogen alkoxyiminoalkyl, cyano or nitro, R ^2a and R ^5a are each fluorine atom, Chlorine atom, bromine atom, alkyl optionally substituted with X, alkoxy optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, substituted with X Alkylsulfonyl which may be substituted with X, alkylsulfenyloxy which may be substituted with X, alkylsulfinyloxy which may be substituted with X, alkylsulfonyloxy which may be substituted with X, amino, alkylamino, dialkylamino, formyl, cyano Or nitro (X Is as described above, and U is a bromine atom or an iodine atom.

As a metal cyanide in reaction [C], 1 type (s) or 2 or more types can be suitably selected from copper cyanide, zinc cyanide, potassium cyanide, etc., for example. The metal cyanide can be used in an amount of 1 to 30 times mol, preferably 1 to 15 times mol for the compound of formula (I-2).
Reaction [C] can be normally performed in presence of a solvent. The solvent may be any solvent as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, dimethoxyethane; acetonitrile, propionitrile, N, N- One or two or more kinds can be appropriately selected from polar aprotic solvents such as dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, N, N-dimethylacetamide, and N-methylpyrrolidone.

The reaction [C] can be carried out in the presence of a palladium catalyst if desired. As a palladium catalyst, 1 type (s) or 2 or more types can be suitably selected from tetrakis triphenylphosphine palladium, bistriphenylphosphine palladium dichloride, etc., for example.
The reaction [C] can be carried out in the presence of a metal iodide if desired. As a metal iodide, 1 type (s) or 2 or more types can be suitably selected from copper iodide, zinc iodide, potassium iodide etc., for example.
The reaction [C] can be usually carried out at 0 to 150 ° C., preferably 10 to 100 ° C., and the reaction time is usually about 0.1 to 24 hours, preferably about 0.5 to 12 hours. Can do.

A, Q ¹ , R ^1a , R ^2a , R ³ , R ⁴ , m, n, and U are as described above.
Carbon monoxide in the reaction [D] can be used in an amount of 1 to 200 times mol, preferably 1 to 50 times mol, of the compound of the formula (I-2).
As a hydrogen donor in reaction [D], 1 type (s) or 2 or more types can be suitably selected from a tributyltin hydride, a poly (methylhydrosiloxane), a trioctyl silyl hydride etc., for example. The hydrogen donor can be used in an amount of 1 to 2 moles, preferably 1 to 1.5 moles relative to the compound of formula (I-2).
Reaction [D] can be normally performed in presence of a palladium catalyst. As a palladium catalyst, 1 type (s) or 2 or more types can be suitably selected from what was mentioned by the said reaction [C] etc., for example.

Reaction [D] can be normally performed in presence of a solvent. Any solvent may be used as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic carbon such as pentane, hexane, heptane, octane and cyclohexane. Hydrogen; ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, dimethoxyethane; acetonitrile, propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, N, N 1 type (s) or 2 or more types can be appropriately selected from polar aprotic solvents such as dimethylacetamide and N-methylpyrrolidone.
The reaction [D] can be usually carried out at 0 to 150 ° C., preferably 10 to 100 ° C., and the reaction time can be usually about 0.5 to 24 hours, preferably about 1 to 12 hours. .

^{A, R 3, R 4,} m and n are as defined above, ^{Q 2} is has been or 4-pyridyl substituted with may also be 3-pyridyl or R ^5b which is substituted with R ^5b, R ^1b is Fluorine atom, chlorine atom, bromine atom, alkyl optionally substituted with X, alkenyl optionally substituted with X, alkynyl optionally substituted with X, hydroxy, alkoxy optionally substituted with X, substituted with X Alkylcarbonyl which may be substituted, carboxyl, alkoxycarbonyl which may be substituted with X, alkylsulfenyl which may be substituted with X, alkylsulfinyl which may be substituted with X, alkylsulfonyl which may be substituted with X, Alkylsulfenyloxy which may be substituted with X, alkylsulfinyloxy which may be substituted with X, alkylsulfonyloxy which may be substituted with X Shi, amino, alkylamino, dialkylamino, halogen may be substituted by alkoxyiminoalkyl, cyano or nitro (X is as defined above), R ^2b and R ^5b are each halogen, may be substituted by X Alkyl, alkoxy optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, alkylsulfonyl optionally substituted with X, alkyl optionally substituted with X Sulphenyloxy, alkylsulfinyloxy optionally substituted with X, alkylsulfonyloxy optionally substituted with X, amino, alkylamino, dialkylamino, cyano or nitro.

  Examples of the fluorinating agent in the reaction [E] include diethylaminosulfur trifluoride, [bis (2-methoxyethyl) -amino] sulfur trifluoride, xenon fluoride, and 2,2-difluoro-1,3-dimethyl. One type or two or more types can be appropriately selected from imidazolidine, sulfur tetrafluoride and the like. The fluorinating agent can be used in an amount of 1 to 10 times mol, preferably 1 to 4 times mol, of the compound of formula (I-5).

Reaction [E] can be normally performed in presence of a solvent. As the solvent, any solvent inert to the reaction may be used. For example, aliphatic hydrocarbons such as pentane, hexane, heptane, octane, isooctane and cyclohexane; aromatics such as benzene, toluene and xylene Group hydrocarbons: halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, fluorinated trichloromethane, dichloroethane, trichloroethane, dichloroethylene; diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, dimethoxyethane 1 type, or 2 or more types can be suitably selected from such ethers.
The reaction [E] can be carried out under an inert gas atmosphere if desired. Examples of the inert gas include gases such as nitrogen, helium, and argon.
The reaction [E] can usually be carried out at −78 to 40 ° C., preferably −40 to 25 ° C., and the reaction time is usually about 2 to 24 hours, preferably about 5 to 15 hours. .

The compound of the above formula (II) is a known compound or can be produced according to known materials. The compound of the formula (II) can be produced, for example, according to the method described in Synthesis, 1980, page 505 or a modification thereof.
Many of the compounds of formula (III) are known compounds or can be prepared according to known materials. The compound of Formula (III) can be manufactured, for example according to the method described in the schemes 9-22 in WO03 / 24222, or it according to it. In the compound of formula (III), a compound in which -COOH is substituted at the 5-position of the pyrazole ring can be produced, for example, according to the following reaction [F].

Q, R ² and n are as described above, and B is halogen. Examples of the halogen include fluorine, chlorine, bromine, and iodine atoms. The compound of formula (VI) is a known compound.
The first step of reaction [F] can usually be carried out in the presence of a base and a solvent.
Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrides such as sodium hydride and potassium hydride; Alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tertiary butoxide; trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidino Pyridine, N-methylmorpholine, N, N-dimethylaniline, N, N-diethylaniline, N-ethyl-N-methylaniline, 1,8-diazabicyclo [5.4.0] -7-undecene, 1,4 -Diazabicyclo [2.2.2] o Tertiary amines such as Tan; n-butyl lithium, can be appropriately selected one or more kinds of such alkyl lithium, such as tert- butyl lithium. The base can be used in an amount of 1 to 10 times mol, preferably 1.2 to 5 times mol for the compound of formula (VI).

The solvent may be any solvent that is inert to the reaction. For example, acetonitrile, propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, N, N— One or two or more types can be appropriately selected from polar aprotic solvents such as dimethylacetamide and N-methylpyrrolidone.
The first step of the reaction [F] can be carried out under an inert gas atmosphere if desired. Examples of the inert gas include gases such as nitrogen, helium, and argon.
The first step of the reaction [F] can usually be carried out at 0 to 160 ° C., preferably 10 to 130 ° C., and the reaction time is usually about 1 to 72 hours, preferably about 2 to 60 hours. Can do.

  Examples of the oxidizing agent in the second step of the reaction [F] include alkali metal salts of halous acids such as sodium chlorite, potassium chlorite, and sodium bromate; potassium permanganate, permanganate One or two or more kinds can be appropriately selected from alkali metal salts or ammonium salts of permanganic acid such as barium and ammonium permanganate. The oxidizing agent can be used in an amount of 1 to 10 times mol, preferably 2 to 8 times mol, of the compound of formula (VII).

The 2nd process of reaction [F] can be normally performed in presence of a solvent. The solvent may be any solvent that is inert to the reaction. For example, acetonitrile, propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, N, N— Polar aprotic solvents such as dimethylacetamide and N-methylpyrrolidone; alcohols such as methanol, ethanol and t-butanol; ketones such as acetone and ethylmethylketone; halogens such as methylene chloride, chloroform and dichloroethylene 1 type or 2 types or more can be suitably selected from hydrocarbons; water etc.
The second step of the reaction [F] can be performed in the presence of a pH adjusting agent if desired. Examples of the pH adjuster include sodium acetate and sodium dihydrogen phosphate dihydrate.
The second step of the reaction [F] can usually be carried out at -20 to 130 ° C, preferably -5 to 110 ° C, and the reaction time is usually about 1 to 24 hours, preferably about 2 to 15 hours. can do.

The compound of the above formula (IV) is a known compound or can be produced according to known materials. For example, the compound of the formula (IV) can be prepared by the method described in Org. Prep. Proceed. Int., 1993, Vol. 25, page 589, the method described in Schemes 8 to 10 in WO 03/24222, or the like. It can be manufactured similarly.
The compound of the formula (V) includes a novel compound. The compound can be produced by the Gabriel method, but those in which R ⁴ is a hydrogen atom can be produced, for example, according to the following reaction [G].

A is as described above, T is halogen, —OSO ₂ G (G is a sulfonic acid ester residue) or —OH, and when T is halogen or —OSO ₂ G, M is sodium or potassium, When T is —OH, M is a hydrogen atom. Examples of the sulfonic acid ester residue include C _1-6 alkyl such as methyl and ethyl; phenyl optionally substituted with C _1-6 alkyl, and the like.

The first step in reaction (G) is, T is halogen or -OSO 2 _G, and M is sodium or potassium, can be carried out usually in the presence of a solvent.
The solvent may be any solvent as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane and dimethoxyethane; aromatics such as benzene, toluene and xylene Hydrocarbons; polar aprotic solvents such as acetonitrile, propionitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, N, N-dimethylacetamide, N-methylpyrrolidone; methanol , Ethanol, propanol, normal butanol, alcohols such as tertiary butanol, and the like can be appropriately selected from one or more.
The first step of the reaction [G] is usually 0 to 150 ° C., preferably 30 to 110 ° C. when T is halogen or —OSO ₂ G and M is sodium or potassium. The reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours.

The first step of the reaction [G] can be usually carried out according to the Mitsunobu method when T is —OH and M is a hydrogen atom. For example, in the presence of a solvent, a dialkylazodicarboxylate and This can be done using triphenylphosphine. The dialkylazodicarboxylate and triphenylphosphine can be used in an equimolar amount with respect to the compound of formula (VIII). Examples of the dialkyl azodicarboxylate include diethyl azodicarboxylate and diisopropyl azodicarboxylate.
The solvent may be any solvent as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, dimethoxyethane; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, dichloroethane 1 type, or 2 or more types can be appropriately selected from halogenated hydrocarbons such as trichloroethane and dichloroethylene; aromatic hydrocarbons such as benzene, toluene and xylene.

  The first step of the reaction [G] can be carried out usually at 0 to 80 ° C., preferably 20 to 60 ° C. when T is —OH and M is a hydrogen atom. The time can be about 0.5 to 24 hours, preferably about 1 to 16 hours.

The 2nd process of reaction [G] can be normally performed by decomposing | disassembling the compound of Formula (X) using a hydrazine in presence of a solvent. The hydrazine can be generally used in an equimolar amount with respect to the compound of the formula (X).
The solvent may be any solvent as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane and dimethoxyethane; aromatics such as benzene, toluene and xylene Hydrocarbons: One or two or more kinds can be appropriately selected from alcohols such as methanol, ethanol, propanol, normal butanol, and tertiary butanol.
The second step of the reaction [G] can be carried out usually at 0 to 140 ° C., preferably 30 to 100 ° C., and the reaction time is usually about 0.5 to 24 hours, preferably about 2 to 12 hours. can do.

  The desirable aspect of the pest control agent containing this invention compound is described below. The pest control agent containing the compound of the present invention includes, for example, various pest control agents that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural pest control agents, and pest control agents that parasitize animals, that is, animal parasitics. It is particularly useful as a biocontrol agent.

  Pesticides for agricultural and horticultural use are useful as, for example, insecticides, acaricides, nematicides, and soil-killing insecticides. Plant parasitic mites such as rustic mites, mites, coral, weevil, lotus moth, codling moth, ball worm, cigarette bud worm, maiiga, kobonomeiga, chanokokakumonhamaki, apple kokumonmonmakaki, peach sinking moth, ashhimeshinki, tamanayaga, kaburaya Colorado potato beetle, cucumber beetle, ball weevil, aphids, leafhoppers, leafhoppers, scale insects, stink bugs, whitefly, thrips, grasshoppers, fly flies, scarabs, ants, leafworms, etc. Agricultural pests; plant parasitic nematodes such as root-knot nematodes, cyst nematodes, nectar nematodes, rice shinga nematodes, strawberry nematodes, pine wood nematodes; gastropods such as slugs and maimai; , Soil pests such as isopods such as brackish beetles; hygiene pests such as house dust mites, house flies, mosquitoes, cockroaches, etc .; It is effective for controlling clothes, house pests such as moths, chickworms, termites, etc .; indoor dust mites, such as mosquito mites, white leopard mites, and southern ticks. Among them, the agricultural and horticultural pest control agent containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. Moreover, the agricultural and horticultural pesticide containing the compound of the present invention is also effective for controlling various resistant pests against drugs such as organic phosphorus agents, carbamate agents, and synthetic pyrethroid agents. Furthermore, since the compound of the present invention has excellent osmotic transfer properties, soil harmful insects, mites, nematodes by treating agricultural and horticultural pesticides containing the compound of the present invention on the soil It is possible to control pests on the foliage at the same time as the control of gastropods and isopods.

  Another desirable embodiment of the pest control agent containing the compound of the present invention is a farm that comprehensively controls the aforementioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. Examples include horticultural pest control agents.

  The agricultural and horticultural pest control agent containing the compound of the present invention is usually a powder, granule, granule wettable powder, wettable powder, aqueous suspension, oily mixture of the compound and various agricultural auxiliary agents. It is used in various forms such as suspensions, aqueous solvents, emulsions, solutions, pastes, aerosols, microdispersions, etc. It can be in any formulation form. Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch, etc. Water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol Solvents such as: fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkylaryl sulfates, alkyl diglycol ether sulfates Salt, alcohol sulfate ester salt, alkyl sulfonate salt, alkyl aryl sulfonate salt, aryl sulfonate salt, lignin sulfonate salt, alkyl diphenyl ether disulfonate salt, polystyrene sulfonate salt, alkyl phosphate ester salt, alkyl aryl phosphate salt , Styryl aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl aryl phosphorus Anionic surfactants and spreading agents such as acid ester salts, naphthalenesulfonic acid formalin condensate salts; sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polymers Liglyceride, fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, Nonionic surfactants and spreading agents such as polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid ester; olive oil, kapok Oil, castor oil, palm oil, straw oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, Oil, rapeseed oil, linseed oil, tung oil, vegetable oils, and the like or a mineral oil such as liquid paraffin. Each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. In addition to the above-mentioned adjuvants, it can be used by appropriately selecting from those known in the art. For example, a bulking agent, a thickening agent, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a phytotoxicity reduction. Various commonly used adjuvants such as agents and antifungal agents can also be used. The compounding ratio of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10. In actual use of these preparations, use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.

  The application of the agricultural and horticultural pest control agent containing the compound of the present invention cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, type of pests and occurrence status, but generally 0.05 to 800,000 ppm, The active ingredient concentration is preferably 0.5 to 500,000 ppm, and the application amount per unit area is 0.05 to 50,000 g, preferably 1 to 30,000 g, of the present compound per hectare. In addition, application of the agricultural and horticultural pest control agent, which is another desirable embodiment of the pest control agent containing the compound of the present invention, is performed according to the application of the pest control agent. The present invention also includes a method for controlling pests by such an application method, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.

  The application of various preparations or dilutions of agricultural and horticultural pesticides containing the compound of the present invention is usually carried out by a commonly used application method, that is, spraying (eg spraying, spraying, misting, atomizing, spraying). Granule, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.), immersion poison bait, etc. It is also possible to feed livestock with the above-mentioned active ingredient mixed with feed to inhibit the occurrence and growth of harmful insects, particularly harmful insects, in the excreta. It can also be applied by the so-called ultra low volume spray method. In this method, it is possible to contain 100% of the active ingredient.

  In addition, the agricultural and horticultural pest control agent containing the compound of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners, etc. There is. Other pesticides include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. . In particular, a mixed pest control composition in which the compound of the present invention and one or more active compound compounds of other agricultural chemicals are used in combination or in combination is preferable in terms of application range, timing of chemical treatment, control activity and the like. It is possible to improve. The compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be prepared separately and mixed at the time of spraying, or both may be used together. The present invention also includes such a mixed pest control composition.

  The mixing ratio between the compound of the present invention and the active ingredient compound of other agricultural chemicals cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, type of pests and occurrence, but generally 1: 300 to 300: 1, preferably 1: 100 to 100: 1. In addition, the appropriate amount to be applied is 0.1 to 50000 g, preferably 1 to 30000 g as the total active ingredient compound amount per hectare. The present invention also includes a method for controlling pests by a method for applying such a mixed pest control composition.

In the above-mentioned other agricultural chemicals, as an active ingredient compound (generic name; including some pending applications) of insecticides, acaricides, nematicides or soil insecticides, that is, pest control agents, for example, Profenofos ), Dichlorvos, Fenamiphos, Fenitrothion, EPN, Diazinon, Chlorpyrifos-methyl, Acephate, Prothiofos, Phosthiazate, phosphocarb ), Cadusafos, Disulfoton, Chlorpyrifos, Demeton-S-methyl, Dimethoate, Methamidophos, AKD-3088, Parathion An organophosphate compound;
Carbaryl (Carbaryl), Propoxur, Aldicarb, Carbofuran, Thiodicarb, Methomyl, Oxamyl, Ethiofencarb, Pirimicarb, Fenobucarb Carbamate compounds such as Carbosulfan, Benfuracarb;
Nereistoxin derivatives such as Cartap, Thiocyclam, Bensultap;
Organochlorine compounds such as Dicofol, Tetradifon, Endosulfan;
Organometallic compounds such as Fenbutatin Oxide;
Fenvalerate, Permethrin, Cypermethrin, Deltamethrin, Cyhalothrin, Tefluthrin, Etofenprox, Fenpropathrin, ifenthrin B Pyrethroid compounds such as
Diflubenzuron, Chlorfluazuron, Teflubenzuron, Flufenoxuron, Lufenuron, Novaluron, Bistrifluron, Nobiflumuron (Noviflumuron) Urea compounds;
Juvenile hormone-like compounds such as methoprene, Pyriproxyfen, and Fenoxycarb;
Pyridazinone compounds such as Pyridaben;
Fenpyroximate, Fipronil, Tebufenpyrad, Ethiprole, Tolfenpyrad, Acetoprole, Pyrafluprole, Pyriprole, Pyriprole compounds;
Neonicotinoids such as Imidacloprid, Nitenpyram, Acetamiprid, Thiacloprid, Thiamethoxam, Clothianidin, Dinotefuran;
Hydrazine compounds such as Tebufenozide, Methoxyfenozide, Chromafenozide, and Halofenozide;
Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazone compounds, and other compounds such as flonicamid (Flonicamid), buprofezin (Huprofezin), hexithiazox (Hexythiazox), amitraz, chlordimeform Silafluofen, Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr, Indoxacarb, Acequinocyl, Etoxazine, Rox 3-Dichloropropene (1,3-dichloropropene), Diafenthiuron, Benclothiaz, Flufenerim, Pyridalyl, Spirodiclofen, Bifenazate, Spiromesi Fen (Spiromesifen), Spirotetramat, Propargite, Clofentezine, Fluacrypyrim, Flubendiamide, DPX-E2Y45, Cyflumetofen, Cyenopyen, C -0101, compounds such as fenazaquin, metaflumizone, Amidoflumet; and the like. In addition, microbial pesticides such as BT agents, entomopathogenic virus agents, entomopathogenic fungi agents, nematode pathogenic fungi agents; avermectin, emamectin-benzoate, milbemectin, spinosad ( Spinosad), Ivermectin, Lepimectin, and other antibiotics or semi-synthetic substances thereof; natural products such as Azadirachtin and Rotenone can also be used in combination.

In the above-mentioned other agricultural chemicals, as an active ingredient compound of a fungicide (generic name; including some applications), for example, pyrimidinamine compounds such as mepanipyrim, pyrimethanil, and cyprodinil;
Triadimefon, Bitertanol, Triflumizole, Etaconazole, Propiconazole, Penconazole, Flusilazole, Microbutanil, Cyproconazole Cyproconazole), terbuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole Azole compounds such as Oxpoconazole, Sipconazole;
Quinoxaline compounds such as quinomethionate;
Dithiocarbamate compounds such as Maneb, Zineb, Mancozeb, Polycarbamate, Propineb;
Organochlorine compounds such as Fthalide, Chlorothalonil, Quintozene;
Imidazole compounds such as Benomyl, Thiophanate-Methyl, Carbendazim, Cyazofamid;
Pyridinamine compounds such as Fluazinam;
Cyanoacetamide-based compounds such as cymoxanil;
Phenylamide compounds such as Metalaxyl, Oxadixyl, Offace, Benalaxyl, Furalaxyl, Cyprofuram;
Sulfenic acid-based compounds such as dichlofluanid;
Copper-based compounds such as cupric hydroxide and organic copper (Oxine Copper);
Isoxazole-based compounds such as hydroxyisoxazole;
Organophosphorous compounds such as fosetyl-Al, tolclofos-Methyl, S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate ;
N-halogenothioalkyl compounds such as Captan, Captafol, Folpet;
Dicarboximide compounds such as Procymidone, Iprodione, Vinclozolin;
Benzanilide compounds such as Flutolanil, Mepronil, Zoxamide;
Piperazine compounds such as Triforine;
Pyridine compounds such as Pyrifenox;
Carbinol compounds such as Fenarimol and Flutriafol;
Piperidine-based compounds such as Fenpropidine;
Morpholine compounds such as Fenpropimorph;
Organotin compounds such as Fentin Hydroxide and Fentin Acetate;
Urea compounds such as Pencycuron;
Synamic acid compounds such as Dimethomorph;
Phenyl carbamate compounds such as Dietofencarb;
Cyanopyrrole compounds such as fludioxonil and fenpiclonil;
Strobilurin-based compounds such as Azoxystrobin, Kresoxim-Methyl, Metominofen, Trifloxystrobin, Picoxystrobin, Pyraclostrobin;
Oxazolidinone compounds such as Famoxadone;
Thiazole carboxamide compounds such as ethaboxam;
Silylamide compounds such as Silthiopham;
Amino acid amide carbamate compounds such as Iprovalicarb;
An imidazolidine-based compound such as Fenamidone;
Hydroxyanilide compounds such as Fenhexamid;
Benzenesulfonamide compounds such as Flusulfamide;
Atolaquinone compounds; crotonic acid compounds; antibiotics and other compounds such as Isoprothiolane, Tricyclazole, Pyroquilon, Diclomezine, Probenazole, Quinoxyfen, Propamocarb hydrochloride (Propamocarb Hydrochloride), Spiroxamine, Chloropicrin, Dazomet, Metam-sodium; and the like.

  Other pesticides that can be used in combination with or combined with the compounds of the present invention include, for example, active ingredient compounds of herbicides such as those described in the Farm Chemicals Handbook (2002 edition), especially those of soil treatment type. is there.

Examples of animal parasite control agents include ectoparasites that parasitize on the body surface of the host animal (back, armpit, lower abdomen, inner thigh, etc.) and the host animal body (stomach, intestinal tract, lung, heart, liver). It is effective for the control of endoparasites parasitizing blood vessels, subcutaneous tissues, lymphoid tissues, etc., among which it is effective for the control of ectoparasites.
Examples of ectoparasites include animal parasitic mites and fleas. There are so many of these types that it is difficult to list them all.

The animal parasitic mites, for example Boophilus microplus (Boophilus microplus), Rhipicephalus sanguineus (Rhipicephalus sanguineus), Haemaphysalis longicornis (Haemaphysalis longicornis), Haemaphysalis flava (Haemaphysalis flava), Adenophora chima tick (Haemaphysalis campanulata), Isukachimadani (Haemaphysalis concinna), Yamatochimadani (Haemaphysalis japonica), H. kitaokai (Haemaphysalis kitaokai), Iyasuchimadani (Haemaphysalis ias), Ixodes ovatus (Ixodes ovatus), I. nipponensis (Ixodes nipponensis), Schulze ticks (Ixodes persulcatus), Takasago testudinarium (Amblyomma testudinarium), Ootogechimadani (Haemaphysalis megaspinosa ), tick such as Dermacentor reticulatus , Dermacentor taiwanesis ; duck ( Dermanyssus gallinae ); Shidani (Ornithonyssus sylviarum), Torisashidani, such as Southern tri sand mite (Ornithonyssus bursa); Nan iodine tsutsugamushi (Eutrombicula wichmanni), red mites (Leptotrombidium akamushi), L. pallidum (Leptotrombidium pallidum), Fuji chiggers (Leptotrombidium fuji), Tosa mites ( Leptotrombidium tosa), Europe Aki mites (Neotrombicula autumnalis), the United States chiggers (Eutrombicula alfreddugesi), chiggers, such as Miyagawa Tama chiggers (Helenicula miyagawai); Inutsumedani (Cheyletiella yasguri), rabbit Tsumedani (Cheyletiella parasitivorax), Nekotsumedani (Cheyletiella blakei) Tsumedani, such as; rabbits 9,000 mite (Psoroptes cuniculi), Ushishokuhidani (Chorioptes bovis), dog ear mites (Otodectes cynotis), mange mites (Sar coptes scabiei ), mite mites like Notoedres cati ; mite mites like Demodex canis , and the like. Among them, the animal parasite control agent containing the compound of the present invention is particularly effective for controlling ticks.

Examples of fleas include ectoparasite worms belonging to the order Flea ( Siphonaptera ), and more specifically fleas belonging to the family Flea family ( Pulicidae ), Nagano family ( Ceratephyllus ) and the like. Examples of fleas belonging to the family flea family include, for example, dog fleas ( Ctenocephalides canis ), cat fleas ( Ctenocephalides felis ), human fleas ( Purex irritans ), elephant fleas ( Echidnophaga gallinacea ), keops mouse fleas ( Xenopsylla cheopis ) Leptopsylla segnis ), European mouse minnow ( Nosopsyllus fasciatus ), and Yamato mouse minnow ( Monopsyllus anisus ). Among them, the animal parasite control agent containing the compound of the present invention is effective for controlling fleas belonging to the family Flea, particularly dog fleas, cat fleas and the like.

  Other ectoparasites include, for example, lice such as bovine lice, foal lice, sheep lice, bovine white lice, head lice; lice such as dog lice; blood-sucking dipterous pests such as bovine abs, quail sharks, . In addition, examples of endoparasites include nematodes such as lungworms, benthic worms, tuberous worms, gastric parasites, roundworms, and filamentous worms; Tapeworms, such as real tapeworms, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms; Japanese schistosomiasis, fluke such as liver cirrhosis; Examples include protozoa such as Ptosporidium.

  Examples of host animals include various pet animals, livestock, poultry, etc., and more specifically dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (eg, pigeons, parrots, (E.g., nine-bird, bird, parakeet, juvenile pine, canary, etc.), cattle, horses, pigs, sheep, ducks, and chickens. Among them, the animal parasite control agent containing the compound of the present invention is effective for controlling pests parasitic on pet animals or livestock, particularly ectoparasites. Among pet animals or domestic animals, it is particularly effective for dogs, cats, cows or horses.

  When the compound of the present invention is used as an animal parasite control agent, it may be used as it is, and together with suitable adjuvants, powders, granules, tablets, powders, capsules, liquid agents, emulsions, aquatic suspensions, It can also be used in various forms such as an oily suspension. In addition to the above-mentioned preparation forms, any preparation forms used in the normal field can be used as long as the object of the present invention is met. Examples of the adjuvant used in the preparation include anionic surfactants and nonionic surfactants exemplified as the above-mentioned preparation adjuvants for agricultural and horticultural pest control agents; positive agents such as cetyltrimethylammonium bromide. Ionic surfactants: water, acetone, acetonitrile, monomethylacetamide, N, N-dimethylacetamide, N, N-dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, Isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl Solvents such as ether, diethylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; oxidations such as butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium metabisulfite, propyl gallate, sodium thiosulfate Inhibitors; Film forming agents such as polyvinylpyrrolidone, polyvinyl alcohol, vinyl acetate and vinylpyrrolidone copolymers; vegetable oils and mineral oils exemplified as preparations for the aforementioned agricultural and horticultural pest control agents; lactose, sucrose, glucose , Starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other carriers such as commercially available feed materials. Each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. In addition to the above-mentioned adjuvants, it can be used by appropriately selecting from those known in the field, and further, selected from various adjuvants used in the above-mentioned agricultural and horticultural fields. You can also

The compounding ratio of the compound of the present invention and various adjuvants is usually about 0.1: 99.9 to 90:10. In actual use of these preparations, use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.
Administration of the compound of the present invention to the host animal is performed orally or parenterally. Examples of the oral administration method include a method of administering tablets, liquid agents, capsules, wafers, biscuits, minced meat, and other feeds containing the compound of the present invention. As a parenteral administration method, for example, the compound of the present invention is prepared into an appropriate preparation and then taken into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on For example, a method of administering to the body surface by treatment, pour-on treatment, spray treatment, etc .; a method of embedding a resin piece containing the compound of the present invention under the skin of a host animal, and the like.

The dose of the compound of the present invention to the host animal varies depending on the administration method, administration purpose, disease symptoms, etc., but is usually 0.01 mg to 100 g, preferably 0.1 mg to 10 g, relative to 1 kg body weight of the host animal. Is suitable for administration.
The present invention also includes a method for controlling pests by the administration method or dosage as described above, particularly a method for controlling ectoparasites or endoparasites.
Further, in the present invention, by controlling animal parasitic pests as described above, there are cases where various diseases of host animals caused by them can be prevented or treated. As described above, the present invention includes a prophylactic or therapeutic agent for parasitic animal diseases containing the compound of the present invention as an active ingredient, and a method for preventing or treating parasitic animal diseases.

  When the compound of the present invention is used as an animal parasite control agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, fragrances, It can be mixed with or used in combination with preservatives and the like. Also, if necessary, mix or use with other animal drugs and pesticides such as anthelmintics, anticoccidials, insecticides, acaricides, fleas, nematicides, fungicides, antibacterials, etc. In this case, a more excellent effect may be exhibited. The present invention includes a mixed pest control composition in which various components as described above are mixed or used together, and there is also a method for controlling pests using the composition, particularly a method for controlling ectoparasites or endoparasites. included.

Next, examples of the present invention will be described, but the present invention is not limited thereto. First, synthesis examples of the compound of the present invention will be described.
Synthesis example 1
N- [4-Chloro-2-[[(1-cyclopropylethyl) amino] carbonyl] -6-methylphenyl] -1- (3,5-dichloro-4-pyridyl) -3- (trifluoromethyl) Synthesis of -1H-pyrazole-5-carboxamide (compound No. 1 described later) 1) 5.0 g of 5- (2-furyl) -3-trifluoromethylpyrazole, 4.5 g of 3,4,5-trichloropyridine, carbonic acid A mixed solution of 6.8 g of potassium and 50 ml of N, N-dimethylformamide was reacted at 110 ° C. for 48 hours under a nitrogen stream. After completion of the reaction, the reaction solution was cooled and extracted by adding ethyl acetate and water. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 3/1) to give oily 1- (3,5-dichloro-4-pyridyl). 5.5 g of -5- (2-furyl) -3- (trifluoromethyl) -1H-pyrazole was obtained. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
8.72 (s, 2H), 7.37 (d, 1H, J = 1.5 Hz), 6.96 (s, 1H), 6.40 (dd, 1H, J = 1.8 Hz), 6. 17 (d, 1H, J = 3.6Hz)

2) 5.5 g of 1- (3,5-dichloro-4-pyridyl) -5- (2-furyl) -3- (trifluoromethyl) -1H-pyrazole, sodium dihydrogen phosphate dihydrate 14. A mixed solution of 9 g and 70 ml of acetonitrile was stirred at room temperature for 30 minutes, and then a mixed solution of 21.5 g of sodium chlorite and 70 ml of water was gradually added dropwise while cooling to 0 ° C. After completion of the dropwise addition, the reaction was continued for 12 hours while gradually returning the liquid temperature to room temperature. After completion of the reaction, the reaction solution was adjusted to pH 1.0 with concentrated hydrochloric acid, and extracted repeatedly by adding ethyl acetate. The organic layer was gradually added dropwise to a mixed solution of 32 g of sodium bisulfite and 400 ml of water at 20 ° C. or lower. After stirring at the same temperature for 15 minutes, the organic layer was extracted. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 1- (3,5-dichloro-4-pyridyl) -3- (trifluoromethyl) -1H-pyrazole-5 having a melting point of 127.9 ° C. -4.7 g of carboxylic acid was obtained.

3) A nitrogen stream was added to a mixed solution of 1.0 g of 1- (3,5-dichloro-4-pyridyl) -3- (trifluoromethyl) -1H-pyrazole-5-carboxylic acid, 0.42 ml of pyridine and 20 ml of acetonitrile. Under 0 ° C., 0.3 ml of methanesulfonyl chloride was gradually added dropwise. After completion of the dropwise addition, stirring was continued for 15 minutes at the same temperature, 0.57 g of 2-amino-5-chloro-3-methylbenzoic acid was added thereto, and then 0.87 ml of pyridine was added. After stirring at 0 ° C. for 15 minutes, 0.3 ml of methanesulfonyl chloride was added, and the mixture was allowed to react overnight while gradually returning the liquid temperature to room temperature. After completion of the reaction, the reaction solution was poured into 200 ml of ice water, and the precipitated crystals were collected by filtration. Wash with a mixed solution of 20 ml of acetonitrile and 10 ml of water to give 6-chloro-2- [1- (3,5-dichloro-4-pyridyl) -3- (trifluoromethyl) -1H-pyrazol-5-yl]. 1.0 g of -8-methyl-4H-3,1-benzoxazin-4-one was obtained. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
9.05 (s, 2H), 8.05 (s, 1H), 7.92 (s, 1H), 7.81 (s, 1H), 1.70 (s, 3H)

4) 1.30 g of triethylamine was gradually added dropwise to a mixed solution of 0.77 g of 1-cyclopropylethylamine hydrochloride and 20 ml of tetrahydrofuran, followed by stirring at room temperature for 1 hour. There, 6-chloro-2- [1- (3,5-dichloro-4-pyridyl) -3- (trifluoromethyl) -1H-pyrazol-5-yl] -8-methyl-4H-3,1 -A mixed solution of 1.30 g of benzoxazin-4-one and 15 ml of tetrahydrofuran was gradually added dropwise. After completion of the dropwise addition, the mixed solution was reacted for 30 minutes under reflux. After completion of the reaction, silica gel was added to the reaction solution, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/2) to obtain 0.60 g of the desired product having a melting point of 275.1 ° C.

Synthesis example 2
N- [6-[[(1-Cyclopropylethyl) amino] carbonyl] -4-iodo-2-methylphenyl] -1- (3,5-dichloro-4-pyridyl) -3- (trifluoromethyl) Synthesis of -1H-pyrazole-5-carboxamide (Compound No. 7 described later) To a mixture of 2.7 g of a 50% ether solution of 1-cyclopropylethylamine and 25 ml of tetrahydrofuran was added 2- [1- (3,5-dichloro- 4-pyridyl) -3- (trifluoromethyl) -1H-pyrazol-5-yl] -6-iodo-8-methyl-4H-3,1-benzoxazin-4-one 1.3 g and tetrahydrofuran 5 ml The liquid was gradually added dropwise. After completion of the dropwise addition, the mixture was reacted for 1 hour under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 3/1) to give 0.15 g of the desired product having a melting point of 273.1 ° C. Got.

Synthesis example 3
N- [4-cyano-6-[[(1-cyclopropylethyl) amino] carbonyl] -2-methylphenyl] -1- (3,5-dichloro-4-pyridyl) -3- (trifluoromethyl) Synthesis of -1H-pyrazole-5-carboxamide (Compound No. 8 below) N- [6-[[(1-cyclopropylethyl) amino] carbonyl] -4-iodo-2-methylphenyl] -1- (3 , 5-dichloro-4-pyridyl) -3- (trifluoromethyl) -1H-pyrazole-5-carboxamide in a mixed solution of 1.2 g and tetrahydrofuran 30 ml, cuprous iodide 0.06 g, tetrakistriphenylphosphine palladium 0.15 g and 1.65 g of cuprous cyanide were added. The mixture was reacted under reflux for 5 hours. After completion of the reaction, the reaction solution was filtered through celite and washed thoroughly with ethyl acetate. The filtrate was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 2/1 to 1/1) to obtain 0.7 g of the desired product having a melting point of 246.3 ° C. Got.

Synthesis example 4
N- [4-Chloro-2-[[(1-cyclopropylethyl) amino] carbonyl] -6-methylphenyl] -1- (4-chloro-3-pyridyl) -3- (trifluoromethyl) -1H -Synthesis of pyrazole-5-carboxamide (compound No. 22 described later) 1) To a mixed solution of 25 g of 3-chloropyridine and 15 ml of acetic acid, 50 ml of 30% aqueous hydrogen peroxide was gradually added dropwise at 0 ° C. After completion of dropping, the mixture was reacted at 50 ° C. for 40 minutes, and then reacted at 120 ° C. for 22 hours. After completion of the reaction, the reaction solution was cooled to room temperature, neutralized with potassium carbonate, and 100 ml of water was added. Next, the mixture was extracted 11 times with ethyl acetate and 7 times with dichloromethane, and dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 29.64 g of 3-chloropyridine-N-oxide. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
8.22 (t, 1H, J = 1.2Hz), 8.09 (td, 1H, J = 1.2, 6.4Hz), 7.25 (m, 1H), 7.19 (m, 1H) )

2) 30 ml of concentrated sulfuric acid was gradually added dropwise to 13 g of 3-chloropyridine-N-oxide while cooling at 0 ° C. Next, 22.5 ml of fuming nitric acid was gradually added dropwise, reacted at room temperature for 10 minutes, and then reacted at 100 ° C. for 3 hours. After completion of the reaction, the reaction solution was poured into 500 ml of ice water and neutralized with sodium bicarbonate. Next, the mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over sodium sulfate. The produced solid was washed with diethyl ether to obtain 9.65 g of 3-chloro-4-nitropyridine-N-oxide. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
8.30 (s, 1H), 8.11 (d, 1H, J = 7.2Hz), 7.98 (d, 1H, J = 7.6Hz)

3) 10.1 g of 5- (2-furyl) -3-trifluoromethylpyrazole, 8.78 g of 3-chloro-4-nitropyridine-N-oxide, 13.8 g of potassium carbonate, 30 ml of N, N-dimethylformamide and A mixed solution of 30 ml of tetrahydrofuran was reacted at 80 ° C. for 2 hours. After completion of the reaction, the reaction solution was cooled and extracted by adding ethyl acetate and water. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 2/1 to 1/1) to obtain 3- [5- 5.88 g of (2-furyl) -3- (trifluoromethyl) -1H-pyrazolyl] -4-nitropyridine N-oxide was obtained. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
8.34 (s, 1H), 8.33 (dd, 1H, J = 1.6, 8.8Hz), 8.10 (d, 1H, J = 6.8Hz), 7.33 (d, 1H) , J = 2.4 Hz), 6.89 (s, 1 H), 6.54 (d, 1 H, J = 3.6 Hz), 6.45 (dd, 1 H, J = 2.0, 3.6 Hz)

4) 3- [5- (2-furyl) -3- (trifluoromethyl) -1H-pyrazolyl] -4-nitropyridine 3.89 g of N-oxide, 30 ml of dichloromethane and 4 ml of phosphorus trichloride are reacted at room temperature for 2 hours. I let you. After completion of the reaction, the reaction solution was extracted with dichloromethane and water. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 2/1 to 1/1) to give oily 1- (4-chloro-3- 2.99 g of pyridyl) -5- (2-furyl) -3- (trifluoromethyl) -1H-pyrazole was obtained. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
8.73 (s, 1H), 8.69 (d, 1H, J = 5.2 Hz), 7.56 (d, 1H, J = 5.2 Hz), 7.35 (t, 1H, J = 1) .2 Hz), 6.94 (s, 1 H), 6.35 (dd, 1 H, J = 1.6, 3.6 Hz), 6.05 (d, 1 H, J = 3.6 Hz)

5) 1.99 g of 1- (4-chloro-3-pyridyl) -5- (2-furyl) -3- (trifluoromethyl) -1H-pyrazole, 7.4 g of sodium dihydrogen phosphate dihydrate and After stirring a mixed solution of 100 ml of acetonitrile at room temperature for 30 minutes, a mixed solution of 16 g of sodium chlorite and 50 ml of water was gradually added dropwise while cooling to 0 ° C. After completion of the dropwise addition, the reaction was continued for 12 hours while gradually returning the liquid temperature to room temperature. After completion of the reaction, the reaction solution was adjusted to pH 1.0 with concentrated hydrochloric acid, and extracted repeatedly by adding ethyl acetate. The organic layer was gradually added dropwise to a mixed solution of 30 g of sodium bisulfite and 200 ml of water at 20 ° C. or lower. After stirring at the same temperature for 15 minutes, the organic layer was extracted. After drying over sodium sulfate, the solvent was distilled off under reduced pressure to give 1- (4-chloro-3-pyridyl) -3- (trifluoromethyl) -1H-pyrazole-5-carboxylic acid having a melting point of 130-135 ° C. 1.5 g was obtained. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: DMSO / 300 MHz)
8.86 (s, 1H), 8.73 (d, 1H, J = 5.6 Hz), 7.85 (d, 1H, J = 5.2 Hz), 7.63 (s, 1H)

6) 1- (4-Chloro-3-pyridyl) -3- (trifluoromethyl) -1H-pyrazole-5-carboxylic acid was added to a mixed solution of 0.064 ml of methanesulfonyl chloride and 3 ml of acetonitrile at 0 ° C. A mixed solution of 23 g, 0.11 ml of triethylamine and 3 ml of acetonitrile was added dropwise. After completion of the dropwise addition, stirring was continued at the same temperature for 30 minutes, and 0.15 g of 2-amino-5-chloro-3-methylbenzoic acid was added thereto, and then 0.22 ml of triethylamine was added. After stirring at 0 ° C. for 1.5 hours, 0.064 ml of methanesulfonyl chloride was further added, and the mixture was allowed to react overnight while gradually returning the liquid temperature to room temperature. After completion of the reaction, the reaction solution was extracted with ethyl acetate and water. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 4/1) to give 6-chloro-2- [1- (4-chloro-3 -Pyridyl) -3- (trifluoromethyl) -1H-pyrazol-5-yl] -8-methyl-4H-3,1-benzoxazin-4-one 0.15 g was obtained. The NMR spectrum data of this product is as follows.
¹ H-NMR δppm (Solvent: CDCl ₃ / 300MHz)
8.74 (s, 1H), 8.68 (d, 1H, J = 5.2 Hz), 7.99 (d, 1H, J = 2.4 Hz), 7.55 (d, 1H, J = 5) .2 Hz), 7.52 (s, 1 H), 7.50 (d, 1 H, J = 2.4 Hz), 1.82 (s, 3 H)

7) 0.15 ml of triethylamine was gradually added dropwise to a mixture of 0.064 g of 1-cyclopropylethylamine hydrochloride and 2 ml of tetrahydrofuran, followed by stirring at room temperature for 1 hour. There, 6-chloro-2- [1- (4-chloro-3-pyridyl) -3- (trifluoromethyl) -1H-pyrazol-5-yl] -8-methyl-4H-3,1-benzo A mixture of 0.077 g of oxazin-4-one and 2 ml of tetrahydrofuran was gradually added dropwise. After completion of the dropwise addition, the mixture was reacted for 1 hour under reflux. After completion of the reaction, silica gel was added to the reaction solution, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 2/1) to obtain 0.090 g of the desired product having a melting point of 162-164 ° C.

Next, typical examples of the compounds of the present invention represented by the formula (I) are listed in Table 1, and their physical properties are listed in Table 2. These compounds can be synthesized based on the above-described synthesis examples or various production methods of the compound of the present invention described above.
In Table 1, No. represents compound No., and the position represents the position at which pyrazole is bonded to carbonyl. Further, in Table 1, A1 is -CH ₂ - and [c-Pr], A2 is -CH (Me) - [c- Pr] a, A3 is _{-CH 2 - [c-Pr (} 2-Me) ], A4 represents —CH ₂ — [c-Pr (2,2-Cl ₂ -1-Me)], A5 represents —CH ₂ — [c-Pr (1-Me)], and A6 represents —CH 2. the [c-Bu], A7 and is _{-CH (Me) -CH 2 SCHF 2} , A8 is - - (Me) a (CH _{2) 2} -SCHF _2, the A9 - a (CH _{2) 2} -SOCHF ₂ , A10 is - the _{(CH 2) 2 -SO 2 CHF} 2, A11 is a _{-CH 2 CH (Me) -SCHF 2} , A12 is a -CHO, A13 is _{-CH 2 - [c-Pr (} 2-CF ₃ )], A14 represents —CH (Me) —CH ₂ SCH ₂ CF ₃ , and A15 represents —CO—CH═CH ₂ . In Table 1, Me represents a methyl group, c-Pr represents a cyclopropyl group, c-Bu represents a cyclobutyl group, and Py represents a pyridyl group.
In Table 1, c-Pr (2-Me) is a cyclopropyl group substituted with a methyl group at the 2-position, and 4-Py (3-Cl, 5-Cl) is pyridyl. A 4-pyridyl group substituted with a chlorine atom at each of the 3-position and 5-position of the group is shown, and other similar descriptions are also based thereon.

Next, test examples are described.
Test Example 1 Effect test on Japanese pearl moth Cabbage leaf pieces were immersed for about 10 seconds in a chemical solution prepared so that the concentration of the compound of the present invention was 50 ppm, and air-dried. A moist filter paper was laid on a petri dish having a diameter of 9 cm, and an air-dried piece of cabbage was placed on the filter paper. There, 10 larvae of 2 to 3 years old were released, covered and left in a constant temperature room at 25 ° C. On the 5th day after the release, the mortality was determined, and the mortality was determined by the following formula. Abnormal insects were also considered dead. When the mortality was determined for the compound Nos. 1 to 10, 12 to 26, 28 to 30, 32, 34, 40, 81, 119, 121, 130, 131 and 133 to 149, 90% of all the compounds were obtained. The above high control effect was shown.
Death rate (%) = (Number of dead insects / Number of dead insects) × 100

Test Example 2 Effect test on silver leaf whitefly A pot of cucumber from which one leaf was left and the other leaves were excised was allowed to lay eggs for about 8 to 24 hours by releasing adult silver leaf whitefly. Then, it was left for 7 to 10 days in a constant temperature room with illumination at 25 ° C. After investigating the number of hatched larvae, a chemical solution prepared so that the concentration of the compound of the present invention was 50 ppm was sprayed at a rate of about 3 ml / strain and air-dried. After being left in a constant temperature room at 25 ° C. for 10 to 14 days after the treatment, the number of old larvae and the number of pupae was investigated, and the control value was determined by the following formula. The compound No. 1, 9, 12, 13, 22, 34, 40, 121, 133, 136, 142 and 144 were determined to have a control value of 50 ppm, and all the compounds showed a high control effect of 80% or more. It was.
Control value (%) = (1 − ((Ta × Cb) / (Tb × Ca))) × 100
Ta: Number of old larvae after treatment in the treated area + number of pups Tb: Number of hatched larvae before treatment in the treated group Ca: Number of old larvae after treatment in the untreated group + number of pups Cb: Hatching before treatment in the untreated group Number of larvae

Test Example 3 Effect test on termites A filter paper was placed in a glass petri dish having a diameter of 9 cm, and 1 ml of a chemical solution prepared so that the concentration of the compound of the present invention was 500 ppm was treated. After that, 10 termite ants and 1 soldier ant were released, covered and left in a constant temperature room with illumination at 25 ° C. Six days after the treatment, the number of deaths of craft ants was investigated, and the death rate was determined by the following formula. Abnormal insects were also considered dead. When the death rate was calculated | required about the said compound No. 1, 6, and 8, all the compounds showed the high control effect of 80% or more.
Death rate (%) = (Number of dead craft ants / 10) x 100

Test Example 4 Medicinal Efficacy Test for Phytophthora tick 1 ml (concentration: 10 μg / ml) of an acetone solution of the compound of the present invention is dropped onto a 9 cm diameter petri dish with a micropipette. After the petri dish inner surface is dried, about 100 young ticks are put and covered with a polyethylene sheet and sealed. When the number of rollover (knockdown) ticks after drug contact is observed, the compound of the present invention rolls over most of the ticklet ticks.

Test Example 5 Medicinal Efficacy Test for Cat Fleas 0.5 ml of an acetone solution of the compound of the present invention prepared at 5.3 ppm was dropped into a glass tube (inner diameter 2.6 cm, bottom area 5.3 cm ² , height 12 cm) having a smooth bottom surface. To do. Acetone is evaporated at room temperature to form a dry film containing the compound of the present invention on the bottom surface. When 10 adult cat fleas ( Ctenocephalides felis ) adults (non-blood-sucking adults within 5 days after emergence) are placed and exposed to the compound of the present invention, most cat fleas have a high control effect.

Next, formulation examples are described.
Formulation Example 1
(1) Compound of the present invention 20 parts by weight (2) 72 parts by weight of clay (3) 8 parts by weight of lignin sulfonate 8 parts by weight The above is uniformly mixed to obtain a wettable powder.
Formulation Example 2
(1) Compound of the present invention 5 parts by weight (2) 95 parts by weight of talc The above components are uniformly mixed to form a powder.
Formulation Example 3
(1) Compound of the present invention 20 parts by weight (2) N, N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene alkylphenyl ether 10 parts by weight (4) Xylene 50 parts by weight To make an emulsion.

Formulation Example 4
(1) Clay 68 parts by weight (2) Lignin sulfonic acid soda 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) Fine powder silica 25 parts by weight A mixture of the above components and the present compound 4 : 1 to make a wettable powder.
Formulation Example 5
(1) Compound of the present invention 50 parts by weight (2) Oxidated polyalkylphenyl phosphate-triethanolamine 2 parts by weight (3) Silicone 0.2 parts by weight (4) Water 47.8 parts by weight (5) 5 parts by weight of sodium polycarboxylate and (6) 42.8 parts by weight of anhydrous sodium sulfate are added to the stock solution mixed and pulverized, and the mixture is uniformly mixed, granulated and dried to obtain a granulated wettable powder.
Formulation Example 6
(1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene phosphate ester 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1) to (3) is uniformly mixed in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove the acetone and form granules.

Formulation Example 7
(1) The compound of the present invention 2.5 parts by weight (2) N-methyl-2-pyrrolidone 2.5 parts by weight (3) soybean oil 95.0 parts by weight (ultra low volume formulation).
Formulation Example 8
(1) Compound of the present invention 40 parts by weight (2) Oxidated polyalkylphenyl phosphate-triethanolamine 2 parts by weight (3) Silicone 0.2 part by weight (4) Xanthan gum 0.1 part by weight (5) Ethylene glycol 5 parts by weight (6) Water 52.7 parts by weight The above is uniformly mixed and pulverized to obtain an aqueous suspension.
Formulation Example 9
(1) Compound of the present invention 10 parts by weight (2) Diethylene glycol monoethyl ether 90 parts by weight The above components are uniformly mixed to form a solution.

Claims (9)

Formula (I):

(Wherein, A is a carbonyl substituted with alkyl or D-substituted with Y, Q is has been or 4-pyridyl substituted with or 3-pyridyl, or R ⁵ to be substituted with R ^5, R ¹ is halogen, alkyl optionally substituted with X, alkenyl optionally substituted with X, alkynyl optionally substituted with X, hydroxy, alkoxy optionally substituted with X, formyl, substituted with X May be alkylcarbonyl, carboxyl, alkoxycarbonyl optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, alkylsulfonyl optionally substituted with X, X Alkylsulfenyloxy which may be substituted, alkylsulfinyloxy which may be substituted with X, alkyls which may be substituted with X Honiruokishi, substituted amino, alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, halogen optionally substituted alkoxyiminoalkyl, cyano or nitro, each of R ² and R ⁵ are halogen, X Alkyl, optionally substituted with X, alkoxy optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, alkylsulfonyl optionally substituted with X, substituted with X Alkylsulfenyloxy optionally substituted with alkylsulfinyloxy optionally substituted with X, alkylsulfonyloxy optionally substituted with X, amino, alkylamino, dialkylamino, formyl, cyano or nitro, R ³ and R ⁴ each represent a hydrogen atom Is alkyl, X is halogen, alkoxy optionally substituted with halogen, alkylsulfenyl optionally substituted with halogen, alkylsulfinyl optionally substituted with halogen, alkylsulfonyl optionally substituted with halogen, or cyano Y is C3-4 cycloalkyl optionally substituted with at least one substituent selected from the group consisting of halogen, alkyl and haloalkyl; haloalkylsulfenyl; haloalkylsulfinyl or haloalkylsulfonyl; D is substituted with halogen Alkenyl optionally substituted with halogen, alkynyloxy optionally substituted with halogen, alkynyl optionally substituted with halogen or alkynyloxy optionally substituted with halogen, m is an integer of 0 to 4, and n is 1 Is an integer of ~ 2) Anthranilamide compounds, their N- oxide or salt thereof. Formula (I):

(Wherein, A is a carbonyl substituted with alkyl or D-substituted with Y, Q is has been or 4-pyridyl substituted with or 3-pyridyl, or R ⁵ to be substituted with R ^5, R ¹ is halogen, alkyl optionally substituted with X, alkenyl optionally substituted with X, alkynyl optionally substituted with X, hydroxy, alkoxy optionally substituted with X, formyl, substituted with X May be alkylcarbonyl, carboxyl, alkoxycarbonyl optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, alkylsulfonyl optionally substituted with X, X Alkylsulfenyloxy which may be substituted, alkylsulfinyloxy which may be substituted with X, alkyls which may be substituted with X Honiruokishi, substituted amino, alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, halogen optionally substituted alkoxyiminoalkyl, cyano or nitro, each of R ² and R ⁵ are halogen, X Alkyl, optionally substituted with X, alkoxy optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, alkylsulfonyl optionally substituted with X, substituted with X Alkylsulfenyloxy optionally substituted with alkylsulfinyloxy optionally substituted with X, alkylsulfonyloxy optionally substituted with X, amino, alkylamino, dialkylamino, formyl, cyano or nitro, R ³ and R ⁴ each represent a hydrogen atom Is alkyl, X is halogen, alkoxy optionally substituted with halogen, alkylsulfenyl optionally substituted with halogen, alkylsulfinyl optionally substituted with halogen, alkylsulfonyl optionally substituted with halogen, or cyano Y is C3-4 cycloalkyl optionally substituted with at least one substituent selected from the group consisting of halogen, alkyl and haloalkyl; haloalkylsulfenyl; haloalkylsulfinyl or haloalkylsulfonyl; D is substituted with halogen Alkenyl optionally substituted with halogen, alkynyloxy optionally substituted with halogen, alkynyl optionally substituted with halogen or alkynyloxy optionally substituted with halogen, m is an integer of 0 to 4, and n is 1 Is an integer of ~ 2) Anthranilamide compounds, a process for the preparation of the N- oxide or a salt thereof,
(1) Formula (II):

(Wherein A, R ¹ , R ³ , R ⁴ and m are as described above), and the formula (III):

(Wherein, Q, R ² and n are as defined above, and Z is a chlorine atom, —OH or C _1-4 alkoxy), or
(2) Formula (IV):

(Wherein, Q, R ¹ , R ² m and n are as described above) and formula (V): A-NHR ⁴ (wherein A and R ⁴ are as described above). Or a compound represented by
(3) Formula (I-2):

^{(Wherein, A, R 3, R 4} , m and n are as defined above, ^{Q 1} is an has been or 4-pyridyl substituted with 3-pyridyl which may be or ^{R 5a} substituted with ^{R 5a} , R ^1a is a fluorine atom, a chlorine atom, a bromine atom, an alkyl optionally substituted with X, an alkenyl optionally substituted with X, an alkynyl optionally substituted with X, a hydroxy, an alkoxy optionally substituted with X , Formyl, alkylcarbonyl optionally substituted with X, carboxyl, alkoxycarbonyl optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, substituted with X Alkylsulfonyl which may be substituted, alkylsulfenyloxy which may be substituted with X, alkylsulfinyloxy which may be substituted with X, There alkylsulfonyloxy, amino, alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, halogen may be substituted by alkoxyiminoalkyl, cyano or nitro, R ^2a and R ^5a are each fluorine atom , Chlorine atom, bromine atom, alkyl optionally substituted with X, alkoxy optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, substituted with X Alkylsulfonyl which may be substituted, alkylsulfenyloxy which may be substituted with X, alkylsulfinyloxy which may be substituted with X, alkylsulfonyloxy which may be substituted with X, amino, alkylamino, dialkylamino, formyl, Cyano or di A compound represented by Toro (X is as described above and U is a bromine atom or an iodine atom) and a metal cyanide, or
(4) Formula (I-2):

(Wherein, A, Q ¹ , R ^1a , R ^2a , R ³ , R ⁴ , m, n and U are as described above), carbon monoxide, and a hydrogen donor. React or
(5) Formula (I-5):

^{(Wherein, A, R 3, R 4} , m and n are as defined above, ^{Q 2} is an has been or 4-pyridyl substituted with 3-pyridyl which may be or R ^5b substituted with R ^5b , R ^1b is a fluorine atom, a chlorine atom, a bromine atom, an alkyl optionally substituted with X, an alkenyl optionally substituted with X, an alkynyl optionally substituted with X, a hydroxy, an alkoxy optionally substituted with X , Alkylcarbonyl optionally substituted with X, carboxyl, alkoxycarbonyl optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, optionally substituted with X A good alkylsulfonyl, an alkylsulfenyloxy optionally substituted with X, an alkylsulfinyloxy optionally substituted with X, an alkylsulfuryl optionally substituted with X Niruokishi, amino, alkylamino, dialkylamino, halogen may be substituted by alkoxyiminoalkyl, cyano or nitro (X is as defined above), R ^2b and R ^5b are each halogen, may be substituted by X Alkyl, alkoxy optionally substituted with X, alkylsulfenyl optionally substituted with X, alkylsulfinyl optionally substituted with X, alkylsulfonyl optionally substituted with X, alkyl optionally substituted with X A sulfenyloxy, an alkylsulfinyloxy optionally substituted with X, an alkylsulfonyloxy optionally substituted with X, amino, alkylamino, dialkylamino, cyano or nitro) and a fluorinating agent And reacting.   A pest control agent comprising the anthranilamido compound of claim 1, its N-oxide or a salt thereof as an active ingredient.   An agricultural and horticultural pest control agent comprising the anthranilamido compound of claim 1, its N-oxide or a salt thereof as an active ingredient.   An insecticide, acaricide or nematicide containing the anthranilamido compound of claim 1, its N-oxide or a salt thereof as an active ingredient.   An animal parasite control agent comprising the anthranilamido compound of claim 1, its N-oxide or a salt thereof as an active ingredient.   A control agent for animal ectoparasites comprising the anthranilamido compound of claim 1, its N-oxide or a salt thereof as an active ingredient.   A prophylactic or therapeutic agent for animal diseases caused by parasites, comprising as an active ingredient the anthranilamido compound, its N-oxide or a salt thereof according to claim 1. A method for controlling pests by applying an effective amount of the anthranilamido compound, its N-oxide or its salt of claim 1.