WO2007020877A1 - Anthranilamide compounds, process for producing these, and pest control agent comprising any of these - Google Patents

Abstract

A novel pest control agent. Also provided are: an anthranilamide compound represented by the formula (I): (I) (wherein A is Y-substituted alkyl or D-substituted carbonyl; Q is optionally R5-substituted 3-pyridyl or optionally R5-substituted 4-pyridyl; R1 is halogeno, optionally X-substituted alkyl, etc.; R2 and R5 each is halogeno, optionally X-substituted alkyl, etc.; R3 and R4 each is hydrogen or alkyl; X is halogeno, optionally halogenated alkoxy, etc.; Y is C3-4 cycloalkyl, etc.; D is alkenyl, etc.; m is an integer of 0-4; and n is 1 or 2); an N-oxide of the compound; and a salt of the compound.

Description

 Specification

 Anthranilamides, production methods thereof, and pest control agents containing them

 Technical field

 [0001] WO01Z70671 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. .

 WO03Z16284 discloses a compound in which 2-pyridyl or phenyl is substituted at the 1-position of the pyrazole ring, while WO04Z67528 discloses a compound in which 2-pyridyl is substituted at the 1-position of the pyrazole ring. ing. 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).

 [0002] Patent Document 1: International Publication WO01Z70671

 Patent Document 2: International Publication WO03Z16284

 Patent Document 3: International Publication WO04Z67528

 Disclosure of the invention

 Problems to be solved by the invention

[0003] A number of pest control agents have been used for many years, but many have various problems such as insufficient efficacy, pests gaining resistance and limiting their use. Therefore, it is desired to develop a new pest control agent with few 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.

 Means for solving the problem

[0004] 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 anthra-amide compound has an extremely high control effect against pests at a low dose, and completed the present invention. That is, the present invention provides a compound of formula (I):

[0005] [Chemical 1]

[0006] wherein A is alkyl substituted with Y or carbo substituted with D, Q may be substituted with R, 3-pyridyl or R ⁵ ! , 4-pyridyl, R ¹ is halogen, alkyl optionally substituted with X, alkenyl optionally substituted with X, alkyl optionally substituted with X, hydroxy, substituted with X Alkoxy, formyl, alkyl carbonyl optionally substituted with X, carboxyl, alkoxy carbonyl optionally substituted with X, alkyl sulfonyl optionally substituted with X, substituted with X Alkylsulfuriel, alkylsulfol optionally substituted with X, optionally substituted with X !, alkylsulfuroxy, optionally substituted with X !, alkylsulfieroxy, X Alkylsulfo-luoxy, which may be substituted with Alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxyiminoalkyl optionally substituted with halogen, cyano or -tro, and R ² and R ⁵ are each substituted with halogen, X Alkyl optionally substituted with X, alkylsulfur optionally substituted with X, alkylsulfuryl optionally substituted with X, alkylsulfol optionally substituted with X , Alkylsulfuroxy which may be substituted with X, alkylsulferoxy which may be substituted with X, alkylsulfoloxy which may be substituted with X, amide-containing alkylamino, dialkylamino, formyl, Shiano or - Toro, R ³ and R ⁴ are each hydrogen atom or alkyl, X is c androgenic, halogen Alkyl which may be substituted with alkyl, alkylsulfur which may be substituted with halogen, alkylsulfuryl which may be substituted with halogen, alkylsulfol which may be substituted with halogen or cyano, Y is halogen A group consisting of alkyl, haloalkyl and C cycloalkyl optionally substituted with at least one selected substituent Roanorequinole; Noroanorequinoles Norefuenole; Noroanorequinoles Nolefininore or Noroanorequinoleolol, D is an alkenyl which may be substituted with halogen, may be substituted with halogen Alkyloxy, substituted with halogen, alkyl or alkyloxy optionally substituted with halogen, m is an integer of 0-4, and n is an integer of 1-2) The present invention relates to an anthracamide compound represented by the formula, an N-oxide thereof, or a salt thereof, a production method thereof, a pest control agent containing them, and the like.

 The invention's effect

 [0007] A pest control agent comprising a novel anthranilamido compound of the formula (I) as an active ingredient is

It has a very high control effect against pests at a low dose.

 BEST MODE FOR CARRYING OUT THE INVENTION

[0008] The number of substitutions of the substituent Y in A, the substituent R ^{5 in} Q, or the substituent X in R ¹ R ² or R ⁵ is

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 number of substituents Y in A is preferably 1. The number of substituents R ^{5 in} Q is preferably 1 to 2.

 The number of substitutions of halogen as a substituent in X, Y or D is 1 or 2 or more. When 2 or more, each halogen may be the same or different. Also, the substitution position of each halogen is! /.

 Of C cycloalkyl in Y

 3-4 The number of substituents of halogen, alkyl or haloalkyl as a substituent may be 1 or 2 or more. When 2 or more, each substituent may be the same or different. In addition, the substitution position of each substituent may be a shift position. C cycloa in Y

 3-4 Alkyl is preferably unsubstituted or has 1 to 5 substituents when it has the above-mentioned substituents.

[0009] The halogen in R ² , R ⁵ , X, Y or D or the halogen as a substituent includes each atom of fluorine, chlorine, bromine or iodine.

The alkyl or alkyl moiety in A, R \ R ² , R ³ , R ⁴ , R ⁵ , X or Y may be either linear or branched. Specific examples thereof include methyl, ethyl, propyl, C, such as isopropyl, n-butyl, tert-butyl, pentyl, hexyl and the like. The alkenyl or alkenyl moiety in R ¹ or D may be straight or branched! /, And examples include bulle, 1-probe, allyl, iso-probe. 1-Butyl, 1,3-Butagel, and 1C Hexane.

 2-6

The alkyl or alkyl moiety in R ¹ or D may be straight-chain or branched! /, And examples thereof include ethynyl, 2-butulyl, 2-pentyl, 3 —C, such as Hekishur.

 2- 6

 Specific examples of C cycloalkyl or cycloalkyl moiety in Y include cyclopropyl.

3- 4

 Or cyclobutyl, with cyclopropyl being the most desirable! /.

 [0010] The salt of the anthracamide compound of the formula (I) includes any one that is agriculturally acceptable. For example, an alkali metal salt such as a sodium salt or a potassium salt is used. Alkaline earth metal salts such as magnesium salts and calcium salts; ammonium salts such as dimethyl ammonium salts and triethyl ammonium salts; such as hydrochlorides, perchlorates, sulfates and nitrates; Inorganic acid salts; organic acid salts such as acetate and methanesulfonate.

 [0011] The anthranilamide-based compound of the formula (I) may have different isomers such as optical isomers and geometric isomers. In the present invention, both isomers and isomer mixtures are present. Is included. The present invention includes various isomers other than those described above within the scope of common technical knowledge in the technical field. In addition, depending on the type of isomer, there may be a chemical structure different from that of the above formula (I). However, since those skilled in the art can sufficiently recognize that they are related to isomers, Obviously, it is within range.

 The anthracamide compound of the formula (I), its N-oxide, or a salt thereof (hereinafter abbreviated as the present compound) is reacted as follows: [A], [B], [C], [D] And [E] can be produced according to the usual production method of N-oxide or salt.

[0012] [Chemical 2]

 (I)

[0013] A, Q,

R ² , R ³ , R ⁴ , m and n are as described above, and Z is a chlorine atom, OH or C aranoloxy.

 -Four

 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 metals such as sodium hydride and potassium hydride. Hydrides: trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, Ν, Ν dimethylaniline, Tertiary amines such as Ν, Ν Jetylaniline, Ν Ethyl-Ν-Methylaniline, 1,8 Diazabicyclo [5.4.0] 7 Undecene, 1,4-Diazabicyclo [2.2.2] octane; η butyllithium, tert butyl Alkyl lithiums such as lithium, etc. It is possible. 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 (II).

[0014] 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, etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, dichloromethane, Chlorohonore Halogenated hydrocarbons such as benzene, toluene, xylene; pentane, hexane, heptane, octane, cyclohexane Non-polar hydrocarbons such as acetonitrile, propio-tolyl, Ν, Ν dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, Ν, Ν dimethylacetamide, Ν-methylpyrrolidone Protic solvents; esters such as methyl acetate, ethyl acetate, propyl acetate; ketones such as acetone, jetyl ketone, methyl ethyl ketone, methyl isobutyl ketone, etc. may be appropriately selected. it can.

 The reaction [Α] can be carried out usually at 20 to + 60 ° C, preferably 0 to 30 ° C when Ζ is a chlorine atom, and the reaction time is usually about 1 to 24 hours, preferably 2 It can be about ~ 12 hours.

 [0015] The reaction [A] can usually be carried out in the presence of a dehydration condensing agent and a solvent when Z is —OH.

 Examples of dehydrating condensing agents include carbodiimides such as Ν, Ν'-dicyclohexylcarbodiimide, 1,3 diisopropylcarbodiimide, 1-ethyl 3- (3 dimethylaminopropyl) carbodiimide hydrochloride; , —Carbo-Rubis—1H—Imidazole, phosphoric acid diester, Jetylphosphorus Dart 1,3,5 Triaza 1,2,4,6 Triphosphorin 2,2,4,4,6, 6 Hexachloride, cyanuric chloride, black isobutyl formate, chlorosulfol isocyanate, trifluoroacetic anhydride and the like.

[0016] The solvent may be any solvent that is inert to the reaction. For example, etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene , Dichloromethane, Chlorophenol, Carbon tetrachloride, Dichloroethane, Trichloroethane, Dichloroethylene, Halogenated hydrocarbons; Benzene, Toluene, Xylene, Aromatic hydrocarbons; Acetonitrile, Propio-tolyl, Ν, Ν Polar aprotic solvents such as dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulfolane, Ν, Ν dimethylacetamide, Ν-methylpyrrolidone; ES such as methyl acetate, ethyl acetate, propyl acetate Tells; Ketones such as acetone, jetyl ketone, methyl ethyl ketone, methyl isobutyl ketone; one or more from aliphatic hydrocarbons such as pentane, hexane, heptane, octane, cyclohexane, etc. Can be appropriately selected.

 Reaction [A] can be carried out usually at 20 to + 60 ° C, preferably 0 to 30 ° C when Z is --OH, and the reaction time is usually about 0.5 to 24 hours, preferably It can be about 1 to 12 hours.

 [0017] The reaction [A] is usually performed in the presence of a base and a solvent when Z is C alkoxy.

 1-4

 be able to.

 Bases include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; trimethylamine, triethylamine, triisopropyl Amines, diisopropylethylamine, pyridine, 4 dimethylaminopyridine, 2,6 dimethylviridine, 4 pyrrolidinopyridine, N-methylmorpholine, Ν, Ν dimethylamine, Ν, Ν jettilin, Ν-ethynole Ν- It is possible to select one or more as appropriate from tertiary amines such as methenorea-phosphorus, 1,8 diazabicyclo [5.4.0] -7 undecene, 1,4 diazabicyclo [2.2.2] octane, etc. it can. 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 (II).

[0018] The solvent may be any solvent that is inert to the reaction. For example, etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene Halogenated hydrocarbons such as benzene, toluene, xylene; pentane, hexane, heptane, octane, cyclohexane, halogenated hydrocarbons such as dichloromethane, chlorophenol, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; Aliphatic hydrocarbons such as hexane; acetonitrile, propio-tolyl, Ν, Ν dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, Ν, Ν dimethylacetamide, Ν-methylpyrrolidone Non polar Ru can be like a protic solvent appropriately selecting one type or two or more types.

The reaction [Α] is usually 0 to 120 ° C, preferably 20 to 80 when Ζ is C alkoxy. The reaction time can be usually about 0.5 to 24 hours, preferably about 1 to 12 hours.

 [Chemical 3]

[B]

[0020] A, Q, R \ R 2, R 4, m and n are as defined above.

 Reaction [B] can usually be carried out in the presence of a solvent.

 Any solvent may be used as long as it is inert to the reaction. For example, etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, dichloromethane, Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, trichloroethane, and dichloroethylene; aromatic hydrocarbons such as benzene, toluene, and xylene; pentane, hexane, heptane, octane, and cyclohexane Aliphatic hydrocarbons such as: acetonitrile, propio-tolyl, Ν, Ν-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, Ν, Ν-dimethylacetamide, Ν-methylpyrrolidone Polar polarity Such as from tons solvent Ru can be appropriately selecting one type or two or more types.

[0021] Reaction [B1 can be carried out in the presence of a base when Α is a carbo substituted with D. it can. As the base, for example, one or more kinds can be appropriately selected from alkali metal hydrides such as sodium hydride and potassium hydride. 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 usually be 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. .

[0022] [Chemical 4]

[0023] A, R ³ , R ⁴ , m and n are as described above, Q ¹ is 3 pyridyl which may be substituted with or 4 pyridyl which may be substituted with R ^5a , and R ^la is fluorine Atom, chlorine atom, bromine atom, alkyl optionally substituted with X, alkaryl optionally substituted with X, alkyl optionally substituted with X, hydroxy, alkoxy optionally substituted with X , Formyl, alkyl carbonyl optionally substituted with X, carboxyl, alkoxy carb optionally substituted with X, alkyl sulfonyl optionally substituted with X, optionally substituted with X Alkylsulfifer, alkylsulfole optionally substituted with X, alkylsulfoxyloxy optionally substituted with X, alkylsulfieroxy optionally substituted with X, optionally substituted with X Alkylsulfo-luoxy, amino Kiruamino, dialkyla Mino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxyiminoalkyl optionally substituted with halogen, cyano or -tro, R ^2a and R

^5a is a fluorine atom, chlorine atom, bromine atom, alkyl optionally substituted with X, alkoxy optionally substituted with X, alkylsulfuryl optionally substituted with X, and optionally substituted with X Alkylsulfuriel, alkylsulfol optionally substituted with X, substituted with X, alkylsulfuroxy, substituted with X, alkylsulfuroxy, substituted with X Alkylsulfo-oxy, amino-containing alkylamino, dialkylamino, formyl, cyano or -toro (X is as described above), and U is a bromine atom or an iodine atom.

[0024] As the metal cyanide in the reaction [C], one or more can be appropriately selected from, for example, copper cyanide, cyanogen zinc, potassium cyanide and the like. 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 (1-2).

 Reaction [C] can usually be carried out in the presence of a solvent. Any solvent may be used as long as it is inert to the reaction.For example, ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; acetonitryl, propio-tolyl, Ν, Ν-Dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, 非, Ν-dimethylacetamide, Ν-methylpyrrolidone and other polar aprotic solvents, etc. can do

[0025] The reaction [C] can be carried out in the presence of a palladium catalyst, if desired. As the palladium catalyst, for example, one kind or two or more kinds can be appropriately selected from tetrakistriphenylphosphine palladium, bistriphenylphosphine palladium dichloride, and the like. Reaction [C] can be carried out in the presence of a metal iodide, if desired. As the metal iodide, for example, one or more kinds can be appropriately selected from copper iodide, zinc iodide, potassium iodide and the like.

Reaction [C] is usually 0 to 150 ° C, preferably 10 to: LOO ° C. The reaction time is usually about 0.1 to 24 hours, preferably about 0.5 to 12 hours. Can do. [0026] [Chemical 5]

[0027] A, Q \ R, R, R, R, m, n, and U are as described above.

 The carbon monoxide in the reaction [D] can be used in an amount of 1 to 200 times mol, preferably 1 to 50 times mol for the compound of the formula (1-2).

 As the hydrogen donor in the reaction [D], one or two or more kinds can be appropriately selected from, for example, tryptyl tin hydride, poly (methylhydrosiloxane), trioctylsilyl hydride and the like. The hydrogen donor can be used in an amount of 1 to 2 times, preferably 1 to 1.5 times the amount of the compound of the formula (1-2).

 Reaction [D] can usually be carried out in the presence of a palladium catalyst. As the radium catalyst, for example, one or more kinds can be appropriately selected from those mentioned in the above reaction [C].

[0028] The reaction [D] can be usually performed in the 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; like pentane, hexane, heptane, octane and cyclohexane. Aliphatic hydrocarbons; jetyl ether, butyl ether, tetrahydrofuran, di Ethers such as dioxane and dimethoxyethane; acetonitrile, propio-tolyl, Ν, Ν — dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, Ν, Ν dimethylacetamide, Ν-methylpyrrolidone One or two or more kinds of polar aprotic solvents can be appropriately selected.

 Reaction [D] is usually 0 to 150 ° C, preferably 10 to: LOO ° C. The reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours. Can do.

[0029] [Chemical 6]

^{[0030] A, R 3,} R 4, m and n are as defined above, Q ² is 4-pyridyl which may be substituted with may be 3-pyridyl or R ^5b is substituted with R ^5b, R ^lb Is a fluorine atom, a chlorine atom, a bromine atom, an alkyl which may be substituted with X, an alkyl which may be substituted with X, an alkyl which may be substituted with X, a hydroxy, which may be substituted with X Good alkoxy, alkyl carbo optionally substituted with X, carboxyl, alkoxy carbo optionally substituted with X, alkyl sulf optionally substituted with X, alkyl sulf optionally substituted with X -Alkyl, alkylsulfol optionally substituted with X, alkylsulfuroxy optionally substituted with X, alkylsulferoxy optionally substituted with X, alkylsulfo optionally substituted with X -Luoxy, Ami-containing alkylami , Dialkylamino, halogen Or an alkoxyiminoalkyl, cyano or -tro (wherein X is as described above), R ^2b and R ^5b are each halogen, alkyl optionally substituted with X, substituted with X Alkoxy, optionally substituted with X, alkylsulfur, optionally substituted with X, alkylsulfur, optionally substituted with X, substituted with X !, alkyl Sulfuroxy, optionally substituted with X !, alkylsulferoxy, optionally substituted alkylsulfooxy, amide-containing alkylamino, dialkylaminate-ciano or nitro.

 [0031] As the fluorine-containing agent in the reaction [E], for example, cetylaminosulfur trifluoride, [bis (2-methoxyethyl) monoamino] sulfur trifluoride, xenon fluoride, 2,2-difluoro-1, 3 One or more of dimethylimidazolidine and sulfur tetrafluoride can be selected as appropriate. The fluorine-containing agent can be used in an amount of 1 to 10 times mol, preferably 1 to 4 times mol for the compound of formula (1-5).

 [0032] The reaction [E] can usually be carried out in the presence of a solvent. The solvent may be any solvent inert to the reaction.For example, aliphatic hydrocarbons such as pentane, hexane, heptane, octane, isooctane, and cyclohexane; benzene, toluene, xylene Aromatic hydrocarbons such as: Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, halogenated trichloromethane, dichloroethane, trichloroethane, dichloroethylene; halogenated hydrocarbons; In addition, one or more kinds can be appropriately selected from ethers such as butyl ether, tetrahydrofuran, dioxane and dimethoxyethane.

 The reaction [E] can be carried out under an inert gas atmosphere if desired. Examples of the inert gas include nitrogen, helium, and argon.

 Reaction [E] can usually be carried out at −78 to 40 ° C., preferably −40 to 25 ° C. The reaction time is usually about 2 to 24 hours, preferably about 5 to 15 hours. Can do.

 [0033] The compound of the 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, p.

Most of the compounds of the formula (III) are known compounds or according to known materials. Can be manufactured. The compound of the formula (III) can be produced, for example, according to the method described in Schemes 9 to 22 in WO03Z24222 or a modification thereof. 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].

 [0034] [Chemical 7]

[0035] QR ² and n are as described above, and B is halogen. Halogen includes 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 metals such as sodium hydride and potassium hydride. Hydrides; sodium methoxide, sodium ethoxide, alkali metal alkoxides such as potassium tert-butoxide; trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminoviridine, 2, 6 Dimethylviridine, 4 Pyrrolidinopyridine, N-Methylmorpholine, Ν, ジ メ チ ル Dimethylaniline, Ν, Ν Jetylaniline, ェ EthyruΝ-Methylaniline, 1,8 Diazabicyclo [5.4.0] 1 7 2.2.2] Tertiary amin like Otatan Η Alkyls such as butyl lithium and tert butyl lithium One or more types can be appropriately selected from rutiles. The base can be used in an amount of 1 to 10 moles, preferably 1.2 to 5 moles based on the compound of the formula (VI).

[0036] The solvent may be any solvent inert to the reaction. For example, aceto-tolyl, propio-tolyl, Ν, ジ メ チ ル -dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide One or two or more polar aprotic solvents such as sulfolane, Ν, Ν-dimethylacetamide, and 、 -methylbicycloidone can be appropriately selected.

 The first step of the reaction [F] can be carried out under an inert gas atmosphere if desired. Examples of inert gases include 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.

 [0037] The oxidizing agent in the second step of the reaction [F] includes, for example, alkali metal salts of nitrous acid such as sodium chlorite, strong chlorite, sodium bromate; permanganic acid One or more kinds of alkali metal salts or ammonium salts of permanganate such as potassium, barium permanganate, and ammonium permanganate can be appropriately selected. 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).

 [0038] The second step of the reaction [F] can be usually performed in the presence of a solvent. Any solvent may be used as long as it is inert to the reaction.For example, acetonitrile, propio-tolyl, Ν, Ν-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, Ν, Ν -Polar aprotic solvents such as dimethylacetamide and Ν-methylpyrrolidone; Alcohols such as methanol, ethanol and tert-butanol; Ketones such as acetone and ethylmethylketone; Methylene chloride and black mouth One or two or more of halogenated hydrocarbons such as form and dichloroethylene; water and the like can be appropriately selected.

The second step of reaction [F] can be carried out in the presence of a pH adjusting agent if desired. Examples of the pH adjuster include sodium acetate and sodium dihydrogen phosphate dihydrate. The

 The second step of 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 2 to 15 It can be about hours.

 [0039] The compound of the above formula (IV) can be produced according to a known compound or a known document. For example, the compound of the formula (IV) can be prepared by the method described in Org. Prep. Proceed. Int., 1993, 25, page 589, the method described in schemes 8 to 10 in WO03Z24222, or the like. Can be manufactured.

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].

 [0040] [Chemical 8]

[0041] A is as described above, T is halogen, —OSO G (G is a sulfonic acid ester residue) or

 2

 Is OH and when T is halogen or OSO G, M is sodium or potassium.

 2

 When T is — OH, M is a hydrogen atom. Examples of the sulfonate residue include C alkyl such as methyl and ethyl;

 1-6 1-6

 Well, for example.

 [0042] In the first step of the reaction (G), T is halogen or —OSO G, and M is sodium or

 2

 In the case of potassium, it can usually be carried out in the presence of a solvent.

Any solvent may be used as long as it is inert to the reaction. For example, jet ether, butyl ether, tetrahydrofuran, dioxane, dimethoxy ester. Ethers such as tan; aromatic hydrocarbons such as benzene, toluene, xylene; acetonitrile, propio-tolyl, Ν, Ν-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, Ν, Polar aprotic solvents such as Ν-dimethylacetamide and Ν-methylpyrrolidone; one or more selected from alcohols such as methanol, ethanol, propanol, normal butanol, and tertiary butanol can do.

 In the first step of the reaction [G], Τ is halogen or —OSO G, and M is sodium or

 2

 In the case of potassium, it can be carried out usually at 0 to 150 ° C, preferably 30 to 110 ° C, and the reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours. it can.

 [0043] The first step of the reaction [G] is a force that can usually be performed according to the Mitsunobu method when T is —OH and M is a hydrogen atom. For example, in the presence of a solvent, a dialkylazo It can be carried out using dicarboxylate and triphenylphosphine. The dialkylazodicarboxylate and triphenylphosphine can be used in an equimolar amount with respect to the compound of formula (VIII). As the dialkylazodicarboxylate,

Examples thereof include jetylazodicarboxylate and diisopropylazodicarboxylate.

 Any solvent may be used as long as it is inert to the reaction. For example, etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, dichloromethane, One or more kinds of halogenated hydrocarbons such as chlorophenol, dichloroethane, trichloroethane, and dichloroethylene; aromatic hydrocarbons such as benzene, toluene, and xylene can be appropriately selected.

 [0044] 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 reaction time is usually about 0.5 to 24 hours, preferably about 1 to 16 hours.

[0045] The second step of the reaction [G] can be usually performed by decomposing the compound of the formula (X) with hydrazine in the presence of a solvent. The hydrazine is usually against the compound of formula (X). About equimolar amounts.

 Any solvent may be used as long as it is inert to the reaction. For example, ethers such as diethyl ether, butyl ether, tetrahydrofuran, dioxane and dimethoxyethane; aromatics such as benzene, toluene and xylene. One or two or more types can be appropriately selected from group hydrocarbons; alcohols such as methanol, ethanol, propanol, nonolemanolebutanol and tertiary butanol.

 The second step of the reaction [G] can be usually carried out 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.

 [0046] Desirable embodiments of the pest control agent containing the compound of the present invention will be 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 parasitic on animals, that is, animals. It is particularly useful as a parasite control agent.

[0047] Pesticides for agricultural and horticultural use include, for example, power useful as insecticides, acaricides, nematicides, and soil-killing insecticides. Specifically, Namihada, -Senamihada, Kanzahadada, Mikanhada Plant parasitic mites such as apple hada, chiyanokorida, mandarin orange, mite, etc .; diamondback moth, weevil, lotus root, codling moth, ball worm, cigarette budworm, maiiga, kono noiga, chinokokakumonhamaki , Momoshin Taiga, Nashihime Shinchii, Tamanayaga, Power Braga, Colorado potato beetle, Urihamushi, Ballui bilbil, Aphids, Pruners, leafhoppers, scale insects, stink bugs, whiteflies, thrips, beetles, beetles Such as moss, ants, and clams Agricultural insect pests; plant parasitic nematodes such as root-knot sentin, cyst-scented, Nesare sentinu, rice singale-scented, strawberry sentinu, pine-nosed sentry, etc .; slugs, maimai, etc. Stomach pests such as gastropods, isopods such as stag beetle, bark beetle, hygiene pests such as house dust mites, house flies, cayenne powers, cockroaches, etc .; Bataga, Azuki beetle, Kokunosutomodoki, Goomushimodashi Stored pests such as moss; clothing, house pests such as Iga, Himekatsubushimushi, termites, etc .; It is effective for controlling 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. In addition, the agricultural and horticultural pest control agent containing the compound of the present invention is also effective in controlling various pests resistant to 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, it is possible to treat soil harmful insects, ticks, and the like by treating the soil with an agricultural and horticultural pesticide containing the compound of the present invention. At the same time as controlling nematodes, gastropods and isopods, it can also control pests on the foliage.

 [0048] Another desirable aspect of the pest control agent containing the compound of the present invention is that the plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. And pesticides for agricultural and horticultural use.

[0049] 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 obtained by mixing the compound and various agricultural adjuvants. , Oily suspension, water solvent, emulsion, liquid, paste, aerosol, microspray, etc. Any formulation used in the field can be used. Adjuvants used in the formulation include diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, mixture of olinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium nitrate, zeolite, starch, etc. Mold carrier: water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, black benzene, cyclohexane, dimethyl sulfoxide, Ν, Ν-dimethylformamide, Ν, Ν-dimethylacetamide,溶 剤 -Methyl-2-pyrrolidone, alcohol and other solvents; fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkylaryl sulfates, Alkyl diglycol ether Sulfates, alcohol sulfates, alkyl sulfonates, alkyl aryl sulfonates, aryl sulfonates, lignite sulfonates, alkyl diphenyl ether disulfonates, polystyrene sulfonates, alkyl phosphates Ester salt, alkylaryl phosphate, styryl aryl phosphate, polyoxyethylene alkyl ether sulfate Salt, polyoxyethylene alkylaryl ether sulfate, polyoxyethylene alkylaryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkylaryl phosphate, naphthalenesulfonic acid formalin condensate Anionic surfactant spreader such as salt of sorbitan; sorbitan fatty acid ester, glycerin fatty acid ester, fatty acid polydaricelide, fatty acid alcohol polydaryl alcohol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer , Polyoxyethylene alkyl ether, polyoxyethylene alkyl ether, polyoxyethylene styryl ether, polyoxyethylene glycol alkyl ether, polyester Nonionic surfactants such as lenglycol, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid ester Agents: olive oil, kapok oil, castor oil, palm oil, straw oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, cut oil, liquid oil, vegetable oil and mineral oil And so on. 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, they can be appropriately selected from those known in the art, for example, extenders, thickeners, anti-settling agents, antifreeze agents, dispersion stabilizers, phytotoxicity reductions. Various commonly used adjuvants such as agents and fungicides 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. It can be added and used.

The application of agricultural and horticultural pesticides containing the compounds of the present invention cannot be defined unconditionally due to differences in weather conditions, formulation, application time, application location, pest type and occurrence, etc. The active ingredient concentration is ˜800,000 ppm, preferably 0.5 to 500,000 ppm. The application amount per unit area is 0.05 to 50 000 g, preferably 1 to 30000 g, of the present compound per hectare. Moreover, the pest control agent containing this invention compound The application of the pest control agent for agricultural and horticultural use, which is another desirable embodiment of the above, is performed in accordance with 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.

 [0051] Various formulations of agricultural and horticultural pesticides containing the compound of the present invention, or their dilutions, are usually applied by a commonly used application method, ie, spraying (eg spraying, spraying, misting, Atomizing, dusting, 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 give livestock a mixture of the above-mentioned active ingredients in feed to inhibit the occurrence and growth of harmful insects, particularly harmful insects, in their excreta. It can also be applied by the ultra-low volume method. In this method, it is possible to contain 100% of the active ingredient.

 [0052] In addition, the agricultural and horticultural pesticide containing the compound of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners, etc. May show sex. Other pesticides include herbicides, insecticides, acaricides, nematicides, soil pesticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. It is done. 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 preferred in terms of application range, timing of chemical treatment, control activity, etc. It is possible to improve. The compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be used separately by mixing them at the time of spraying, or may be used by preparing both together. The present invention also includes such a mixed pest control composition.

[0053] 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, pest type and occurrence, etc. Generally, it is 1: 300 to 300: 1, preferably 1: 100 to 100: 1. The appropriate amount to be applied is 0.1 to 50000 g, preferably 1 to 30000 g as the total amount of active ingredient compounds per hectal. 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 ( Profenofos, Cyclonorevos, Dichlorvos, Fenamithion, Fenitrothion, EPN, Diazinon, Chlorpyrif os-methyl, Acephate, Prothiofos, Phostiazate Fosth iazate), Phosphocarb, Cadusafos, Dislfoton, Chlorpyrifos, Demeton-S-methyl, Dimethoate, Methamidophos, AKD- Organophosphate compounds such as Parathion;

 Power Barbaryl, Propoxur, Aldicarb, Carboforan, Thiodicarb, Methomyl, Oxamyl, Ethiofencarb, Pirimicarb, Pirimicarb Carnomate compounds such as Fenob ucarb, Carbosulfan, Benforacarb;

 Nereistoxin derivatives such as Cartap, Thiocyclam, Bensultap;

 Organochlorine compounds such as Dicofol, Tetradifon, Endosulfan;

 Organometallic compounds such as Fenbutatin Oxide;

 Fenvalerate, Penoremethrin (Permethrin), Cypermethrin (Cypermethr in), Deltamethrin, Deltahalothrin (Cyhalothrin), Tefluthrin, Etofenprox, Fenpropathrin, Fenpropathrin Pyrethroid compounds such as (Bifenthrin);

 Diflubenzuron, Chlorfluazuron, Teflubenzuron, Flufenoxuron, Lufenuron, Novaluron, Bistrifluron, Novifluron Benzo Lurea compounds such as

Metohoprene, Pyriproxyfen, Phenoxycarb (Fenox) juvenile hormone-like compounds such as ycarb);

 Pyridazinone compounds such as Pyridaben;

 Fenpyroximate, Fipronil, Tebu fenpyrad, Ethiprole, Tolfenpyrad, Acetoprole, Pyrafluprole, Pyriprozole, Pyriprole

 Neo-cotinoids such as Imidacloprid, Nitenpyram, Acetamiprid, Thiacloprid, Thiamethoxam, Clothia nidin, Dinoteforan;

 Hydrazine compounds such as Tebufenozide, Methoxyfenozide, Chromafenozide, and Halofenozide;

Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazine compounds, and other compounds include Flonicamid, Buprofezin, Hexythiazox, Amitraz ( Amitraz), Chlordimeform (Ch lordimeform), Silafrofen (Silafluofen), Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr, Indquinocolyl, Indoxaoc Etoxazole), cyromazine, 1,3-dichloropropene, 1,3-dichloropropene, diafenthiuron, Benclothiaz, Flufenerim, pyridylyl, spirodiclo Firo (Spirodiclofen), Bifenazate (Bifenazate) Spiromesifen, Spirotetramat, Propargite, Clofentezine, Fluacrypyrim, Flubendiamide, DPX-E2Y45, Cyflumetofen (Cyflumetofen) (Cyenopyrafen), NNI-0101, compounds such as fenazaquin, Metaflumizone, Amidoflumet; and the like. In addition, microbial agents such as BT agents, entomopathogenic virus agents, entomopathogenic fungi agents, nematode pathogenic fungi agents, etc .; Avenoremectin (Avermectin), Emamectin- Benzoate, Milbemectin ( Milbemectin), Spinosad, Ivermectin, Antibiotics such as pimectin (Lepimectin) or semi-synthetic substances thereof; natural products such as azadirachtin and rotenone can also be mixed and used together.

 In the above-mentioned other agricultural chemicals, as an active ingredient compound (generic name; including some applications), for example, mepa-pyrim (Mepanipyrim), pyrimethanil, cyprodil (Cy prodinil) ) Pyrimidinamine compounds such as

Triadimefon, Bitertanol, Triflumizol _e , Etaconazole, Propiconazole, Penconazole, Flusilazole, Micros Butaninole (Myclobutanil), Cyproconazonole (Cyproconazole), Terbuconazole (Terbuconazole), Hexaconazole (Hexaconazole), Fa ~~ Conan ~~ Norens (Furconazole—cis), Prochloraz (Metconazonole) ), Epoxideconazonore (Epoxiconazole), tetraconazonore (Tetraconazole), azole compounds such as sipconazole (Sipconazole);

 Quinoxaline compounds such as quinomethionate;

 Dithiocarbamate compounds such as Maneb, Zineb, Mancozeb, Polycarba mate, Propineb;

 Organochlorine compounds such as Fthalide, Chlorothalonil, Quintozene;

 Imidazole compounds such as Benomyl, Thiophanate-Methyl, Carbendazim, Cyazofamid;

 Pyridinamine compounds such as Fluazinam;

 Cyanoacetamide compounds such as Cymoxanil;

 Phenolic compounds such as Metalaxyl, Oxadixyl, Offorace, Benalaxyl, Furalaxyl, Cyproforam;

 Sulfenic acid compounds such as dichlofluanid;

Copper-based compounds such as cupric hydroxide and organic copper (Oxine Copper); Isoxazole compounds such as hydroxyisoxazole; Fosety 卜 Al, Torclofos-Methyl, S-Benzyl Ο, Ο-diisopropylphosphorothioate, O-Ethyl S, S—Organic phosphorus compounds such as diphenylphosphlodithioate and aluminium hydrogen phosphonate;

 N-halogenoalkyl compounds such as Captan, Captafol, Folpet;

_{Dicarboximide} compounds such as procymidone, Iprodione, Vinclozolin;

Benth anilide compounds such as Flutol (Flut ₀ lanil), Meprol (Mepronil), Zoxamide;

 Piperazine compounds such as Triforine;

 Pyridine compounds such as Pyrifenox;

 Carbinol compounds such as Fenarimol and Flutriafol Piperidine compounds such as Fenpropidine;

 Morpholine compounds such as Fenpropimorph;

 Organotin compounds such as Fentin Hydroxide and Fentin Acetate;

 Urea-based compounds such as Pencycuron;

 Synamic acid compounds such as Dimethomorph;

 Fercarbamate compounds such as Dietophencarb; Cyanpyrrole compounds such as Fludioxonil and Fenpiclonil;

Oxazolidinone compounds such as Azoxystrobin, Kresoxim-Methyl, Metominofen, Trifloxystrobin, Picoxystrobin (Picoxys Famoxadone); Thiazole carboxamide compounds such as ethaboxam; silylamide compounds such as silthiopham;

 Aminoacid amide carbamate compounds such as Iprovalicarb; Imidazolidine compounds such as Fenamidone;

 Hydoxyxanilide compounds such as fenhexamid;

Benzenesulfonamide compounds such as Flusulfamide; Atolaquinone compounds; Crotonic acid compounds; Antibiotics and other compounds such as I _so prothiolane, Tricyclazole, Pyroquilon, Dichromemidine ( Diclomezine), Purobe mystery one / LES (Probenazole), quinoxyfen (Quinoxyf en), Puropamokanorebu hydrochloride (Propamocarb hydrochloride), spiroxamine (Spiroxami n _e), chloropicrin (chloropicrin), dazomet (dazomet), meta beam sodium salt ( Metam- sodi um);

[0056] Other pesticides that can be mixed or used in combination with the compounds of the present invention include, for example, active ingredients of herbicides such as those described in the Farm Chemicals Handbook (2002 edition), particularly those of soil treatment type. There are things.

[0057] 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, It is effective for the control of endoparasites that parasitize the heart, liver, blood vessels, subcutaneous, lymphatic thread, and the like, and is particularly effective for the control of ectoparasites.

 Examples of ectoparasites include animal parasitic mite fleas. These types are very difficult to list, so here are some examples.

[0058] Animal parasitic mites include, for example, Boophilus microplus, Rhipicephalus sanguineus, Phytophthora, eu (Haemaphvsalis longicorni s), Kitani tick (Haemaphvsalis flava), burdock mite ph , Chair power zima, 'e (Haemaphvsalis concinna), yamato chimata-(Haemaphvsalis ja ^ onica), Haemaphvsalis kitaokai, Haemaphvsalis ias, tick (Ixodes ovatus) Ixodes nipponensis), sur zuemata, ii (Ixodes persulcatus), Takasago Kiramata (Amblvomma testudinarium) Ticks, such as the genius Tematani (Haemaphvsalis megaspinosa), Acarid tick (Dermacentor r eticulatus), Dermacentor taiwanesis; Duck (Dermanvssus gallinae): Trisanta Birds such as Eustrombicula wic hmanni, Leptotrombidium akamushi, Leptotrom bidium pallidum, Leptotrombidium luii, trosaula, trosaula mtro Cuckoo beetle (Eutrombicula alfreddugesi), crested reptile of Helenicula mivagawai: Chinlet tick (Chevletiella m rasitivorax); Hymenidic towns such as Psoroptes cuniculi, Chorioptes bovis, Otodectes cvnotis, Sarcoptes scabiei, Notoedres cati: Demodex canis Among them, the animal parasite control agent containing the compound of the present invention is particularly effective for controlling ticks.

[0059] Examples of fleas include ectoparasite worms belonging to the order Flea (Siphonaotera), and more specifically fleas belonging to the family Flea (Pulicidae), Nagano (CerateDhyllus), etc. . Examples of fleas belonging to the family Fleas include: Flea (Ctenoce Dhalides canis), Cono (Ctenocephalides felis), Human flea (Pulex irritans), -Echidnoph aga gallinacea, Xenopsvlla cheopis, Examples include fleas (Leptopsvl la segnis), yosoku tsuno ヽ nozuno (Nosopsyllus fasciatus), yamanoshino (Monopsvll us mik), etc. Among them, animal parasite control agents containing the compounds of the present invention include: It is effective for controlling fleas belonging to the family Flea family, especially cynos and cat fleas.

[0060] Other ectoparasites include, for example, lice such as white lice, white lice, white lice, white lice, head lice; white lice such as white lice; blood sucking such as Usiab, Uinu power, and Thmetgebu Diptera pests. Examples of endophytic organisms include nematodes such as lungworms, bench beetles, tuberous worms, gastric parasites, roundworms, and filamentous worms; , Persimmon tapeworm, multi-headed tapeworm, single Tapeworms, tapeworms such as polychaete, Japanese schistosomiasis, fluke such as liver cirrhosis; protozoa such as coccidium, malaria parasite, intestinal granulocyst, toxoplasma, cryptosporidium Etc.

 [0061] Examples of host animals include various pet animals, livestock, poultry, and the like, and more specifically, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (for example, , Pigeons, omme, nine-birds, wild birds, parakeets, pine pine, canary, etc.), sushi, horses, butter, hidge, ducks, etc. Among these, the animal parasite control agent containing the compound of the present invention is effective for the control of pests parasitic on pet animals or livestock, particularly ectoparasites. It is especially effective for dogs, cats, ushi or horses in pets or livestock.

[0062] When the compound of the present invention is used as an animal parasite control agent, it may be used as it is. Also, powders, granules, tablets, powders, capsules, liquid agents, emulsions, aquatic compounds with appropriate adjuvants. It can also be formulated and used in various forms such as a suspension and an oily suspension. In addition to the above-mentioned preparation form, any preparation form that is generally used in this field can be used as long as it is suitable for the purpose of the present invention. Examples of the adjuvant used in the preparation include anionic surfactants and nonionic surfactants exemplified as the aforementioned preparation adjuvants for agricultural and horticultural pest control agents such as cetyltrimethylammonium bromide. Cationic surfactants: water, acetone, acetonitrile, monomethylacetamide, Ν, Ν-dimethylacetamide, Ν, Ν-dimethylformamide, 2-pyrrolidone, Ν-methyl-2-pyrrolidone, kerosene, triacetin, Methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol nore, butinoresin glycol nore, ethylene glycol nole monomethylenoatenore, ethylene glycolenolemonochinenoatenoate, Diethylene Solvents such as ricono-remonomethino-reinotenole, diethyleneglycolenorenoremanolebutenoreatenore, dipropyleneglycololemonomethinoreate, dipropyleneglycolnormalbutylether; butylhydroxyl-sol, butylhydroxytoluene , Anticorrosive agents such as ascorbic acid, sodium metabisulfite, pour pill gallate, sodium thiosulfate; film formation such as polybulurpyrrolidone, polyvinyl alcohol, copolymer of bull pyrrolidone acetate and bull pyrrolidone Agent; Vegetable oils and mineral oils exemplified as the above-mentioned adjuvants for formulation of agricultural and horticultural pesticides; lactose, sucrose, glucose, starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other commercially available feed materials And the like. Each component of these adjuvants

As long as the object power of the present invention is not deviated, one or more kinds can be appropriately selected and used. In addition to the above-mentioned auxiliary agents, they can be appropriately selected from those known in the field, and further, the various auxiliary agents used in the above-mentioned agricultural and horticultural fields are appropriately selected. Can also be used.

[0063] 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. It can be used as a supplement.

 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 in an appropriate formulation and then taken into the body by intravenous injection, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on ) Treatment, pour-on treatment, spray treatment, and the like; and a method of embedding a fat slice containing the compound of the present invention under the skin of a host animal.

 [0064] The dose of the compound of the present invention to the host animal varies depending on the administration method, purpose of administration, disease symptoms, etc., but is usually O.Olmg to: L00g to the body weight lKg of the host animal, preferably 0.1 It is appropriate to administer at a rate of mg to 1 Og.

 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, it may be possible to prevent or treat various diseases of host animals caused by them. Thus, the present invention also includes a prophylactic or therapeutic agent for parasite-derived animal diseases containing the compound of the present invention as an active ingredient, and a method for preventing or treating parasite-derived animal diseases. included.

 [0065] 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, antiphlogistics, bactericides, and coloring agents together with adjuvants. , Fragrances, preservatives and the like can be mixed or used together. If necessary, mix with or use other animal drugs and pesticides such as anthelmintics, anti-coxime, insecticides, acaricides, fleas, nematicides, bactericides, and antibacterials. In this case, the effect may be even better. The present invention includes a mixed pest control composition in which various components as described above are mixed or used together, and a pest control method using the composition, particularly control of ectoparasites or endoparasites. A method is also included.

 Example

 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 Black mouth 2— [[(1-Cyclopropylethyl) amino] carbol]-6 Methylphenol] 1— (3,5 Dichloro-4-pyridyl) 3 (Trifluoromethyl)-1H -Synthesis of Pyrazolu 5 Carboxamide (Compound No. 1 below)

 (1) 5- (2 furyl) 1-3 trifluoromethylpyrazole 5.0 g, 3,4,5 trichloro-orthopyridin 4.5 g, potassium carbonate 6.8 g and Ν, Ν dimethylformamide 50 ml mixed with nitrogen stream The reaction was carried out at 110 ° C for 48 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 anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: n-hexane Z-ethyl acetate = 3Z 1) to give oily 1 (3, 5 dicloate — 4 pyridyl) 5— ( 5.5 g of 2-furyl) 3 (trifluoromethyl) -1H-pyrazole was obtained. The NMR vector data of this product are as follows.

 NMR S ppm (Solvent: CDC1 / 300MHz)

 Three

 8.72 (s, 2H), 7.37 (d, lH, J = 1.5Hz) ゝ 6.96 (s, lH), 6.40 (dd, lH, J = 1.8Hz), 6.1 7 (d, lH ゝ J = 3.6Hz)

[0067] (2) 1— (3,5 Dichloro-4-pyridyl) 5— (2-Furyl) 3— (Trifluoromethyl) -1H pyrazole 5.5g, sodium dihydrogen phosphate dihydrate 14.9g and acetonitrile 7Oml stirred at room temperature for 30 minutes and then cooled to 0 ° C, while sodium chlorite 2 1.5g and water 70ml The mixed solution was gradually added dropwise. After completion of the dropwise addition, the reaction was continued for 12 hours while gradually returning the solution temperature to room temperature. After completion of the reaction, the reaction solution was adjusted to pH 1.0 with concentrated hydrochloric acid, 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 for 15 minutes at the same temperature, the organic layer was extracted. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 1— (3,5 dichloro-4-pyridyl) 3 (trifluoromethyl) 1H pyrazol-5-carboxylic acid with a melting point of 1 27.9 ° C. 4.7g was obtained.

[0068] (3) 1— (3,5 Dichloro-4-pyridyl) 3 (trifluoromethyl) 1H pyrazole

 0.3 ml of methanesulfuryl chloride was gradually added dropwise to a mixed solution of 1.0 g of 5-strong rubonic acid, 0.42 ml of pyridine and 20 ml of acetonitrile in a nitrogen stream at 0 ° C. After completion of the dropwise addition, stirring was continued for 15 minutes at the same temperature, to which 0.57 g of 2 amino-5 black mouth 3-methylbenzoic acid was added, 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 while gradually returning the solution 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. 6 2 2 [1— (3,5 dichloro 1 -4-pyridyl) 1 3 (trifluoromethyl) 1 H pyrazole 5 yl] 8 Methyl 4H-3,1 benzoxazine-4-one l.Og was obtained. The NMR vector data of this product are as follows.

 NMR S ppm (Solvent: CDC1 / 300MHz)

 Three

 9.05 (s, 2H) ゝ 8.05 (s, lH), 7.92 (s, lH), 7.81 (s, lH), 1.70 (s, 3H)

[0069] (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 — black mouth 2— [1— (3,5 dichloro 1 4 pyridyl) 3 (trifluoromethyl) 1H— pyrazole 5 yl] 8 methyl 4H— 3, 1 benzoxazin 4-one 1.30 g and A mixture of 15 ml of tetrahydrofuran was gradually added dropwise. After completion of the dropwise addition, the mixture was reacted for 30 minutes under reflux. After completion of the reaction, silica gel is added to the reaction solution and the solvent is removed under reduced pressure. Distilled off. The residue was purified by silica gel column chromatography (eluent: n-hexane Z ethyl acetate = 1Z2) to obtain 0.60 g of the desired product having a melting point of 275.1 ° C.

[0070] Synthesis Example 2

 N— [6— [[(1 Cyclopropylethyl) amino] carbol] 4 — 2-methylphenyl] 1— (3, 5 dichloro4-pyridyl) 3 (trifluoromethyl) 1H pyrazo Synthesis of 5-carboxamide (Compound No. 7 below)

 To a mixed solution of 2.7 g of 50% ether solution of 1-cyclopropylethylamine and 25 ml of tetrahydrofuran, add 2- [1- (3,5 dichloro-4-pyridyl) 3 (trifluoromethyl)-1 H -pyrazole 5 yl] 6-odd 8-methyl 4H-3,1 benzoxazin-4-one 1.3 g and tetrahydrofuran 5 ml were gradually added dropwise. After completion of dropping, 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 Z ethyl acetate = 3Zl) to obtain 0.15 g of the desired product having a melting point of 273.1 ° C. It was.

[0071] Synthesis Example 3

 N— [4 Cyan 6— [[(1-Cyclopropylethyl) amino] carbol] -2 methylphenyl] 1— (3,5 dichloro 4 pyridyl) 3 (trifluoromethyl)-1H- Synthesis of Pyrazo Iru 5-Carboxamide (Compound No. 8 below)

 N— [6— [[((1 Cyclopropylethyl) amino] carbol] 4) 2-methylphenyl] 1— (3,5 dichloro 4-pyridyl) 3 (trifluoromethyl) 1H pyrazole To a mixture of 1.2 g of 1-carboxamide and 30 ml of tetrahydrofuran, 0.06 g of cuprous iodide, 0.15 g of tetrakistriphenylphosphine palladium 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 thoroughly washed with ethyl acetate. The filtrate was washed with saturated aqueous sodium hydrogen carbonate solution and saturated Japanese 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 Z ethyl acetate = 2Z1-: LZD) to obtain 0.7 g of the desired product having a melting point of 246.3 ° C.

[0072] Synthesis Example 4

N— [4 Black mouth 2— [[(1-Cyclopropylethyl) amino] carbole] -6 methyl 1] (4—Black 1-Pyridyl) 3 (Trifluoromethyl) -1H-pyrazole 5 Carboxamide (Compound No. 22 below)

 (1) 3 ml of 30% aqueous hydrogen peroxide was gradually added dropwise to a mixed solution of 25 g of pyridine and 15 ml of acetic acid under cooling at 0 ° C. After completion of the dropwise addition, 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. Subsequently, extraction was carried out 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 vector data of this product are as follows.

 NMR S ppm (Solvent: CDC1 / 300MHz)

 Three

 8.22 (t, lH ゝ J = 1.2Hz) ゝ 8.09 (td, lH, J = 1.2, 6.4Hz), 7.25 (m, lH) ゝ 7.19 (m, l H)

 [0073] (2) 30 ml of concentrated sulfuric acid was gradually added dropwise to 13 g of 3-chloropyridine-N-oxide under cooling at 0 ° C. Next, 25.5 ml of fuming nitric acid was gradually added dropwise and 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, extraction was performed with ethyl acetate, and the organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The resulting solid was washed with jetyl ether to obtain 9.65 g of 3-chlorodibutyl 4-ditropyridine N-oxide. The NMR vector data of this product are as follows.

 NMR S ppm (Solvent: CDC1 / 300MHz)

 Three

 8.30 (s, lH), 8.11 (d, lH ゝ J = 7.2Hz), 7.98 (d, lH ゝ J = 7.6Hz)

[0074] (3) 5— (2 Furyl) -3 Trifluoromethylpyrazole 10. lg, 3 Black mouth 4-Nitropyridine—N-oxide 8.78 g, Potassium carbonate 13.8 g, Ν, Ν Dimethylformamide 30 m A mixed solution of 1 and 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 dried over sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography (eluent: n-hexane Z ethyl acetate = 2Z 1-1 Z 1), with a melting point of 115—120 ° C 3— [5 — (2-Furyl) 3 (trifluoromethyl) 1H-villazolyl] — 4-ditropyridine N-oxide 5.88 g was obtained. NMR ^ vector vector of this thing The data is as follows.

 NMR S ppm (Solvent: CDC1 / 300MHz)

 Three

 8.34 (s, lH), 8.33 (dd, lH ゝ J = 1.6, 8.8Hz), 8.10 (d, lH ゝ J = 6.8Hz), 7.33 (d, lH, J = 2.4Hz), 6.89 (s, lH ), 6.54 (d, lH, J = 3.6 Hz), 6.45 (dd, lH, J = 2.0, 3.6 Hz)

 [0075] (4) 3— [5— (2-Furyl) 3 (trifluoromethyl) 1H pyrazolyl]-4 Nitropyridine N-oxide 3.89 g, dichloromethane 30 ml and phosphorus trichloride 4 ml 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 the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (eluent: n-hexane Z ethyl acetate = 2Z 1-1 / 1) to give oily 1- (4 Pyridyl) 5- (2 furyl) 1-3 (trifluoromethyl) 1H pyrazole 2.99 g was obtained. The NMR ^ vector data of this is as follows.

 NMR S ppm (Solvent: CDC1 / 300MHz)

 Three

 8.73 (s, lH) ゝ 8.69 (d, lH ゝ J = 5.2Hz), 7.56 (d, lH ゝ J = 5.2Hz), 7.35 (t, lH, J = 1.2Hz), 6.94 (s, lH) ゝ6.35 (dd, lH, J = 1.6, 3.6Hz), 6.05 (d, lH, J = 3.6Hz

)

 [0076] (5) 1— (4 Chlo-one 3-pyridyl) 5— (2-Furyl) 3 (trifluoromethyl) 1H —Pyrazole 2.99 g, Sodium dihydrogen phosphate dihydrate 7.4 g and Acetonitrile 100 ml After the mixture solution was stirred at room temperature for 30 minutes, a solution mixture 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 solution was allowed to react for 12 hours while gradually returning the solution temperature to room temperature. After completion of the reaction, the reaction solution was adjusted to pHl.O with concentrated hydrochloric acid, and ethyl acetate was added for repeated extraction. 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 for 15 minutes at the same temperature, the organic layer was extracted. After drying over sodium sulfate, the solvent is distilled off under reduced pressure, melting point 130—135 ° C 1 — (4 Kuroguchi 1-3 pyridyl) 3 (trifluoromethyl) -1H-pyrazole 5 carboxylic acid 1.5 g Got. The NMR spectrum data of this product are as follows.

NMR S ppm (Solvent: DMSO / 300MHz) 8.86 (s, lH), 8.73 (d, lH ゝ J = 5.6Hz), 7.85 (d, lH ゝ J = 5.2Hz), 7.63 (s, lH) [0077] (6) 0.064 ml of methanesulfuryl chloride and In a mixed solution of 3 ml of acetonitrile, 0 ° C, 1— (4-chlorodiethyl 3-pyridyl) 3— (trifluoromethyl) -1H-pyrazole 5-force rubonic acid 0.23 g, triethylamine 0.1 lml and acetonitrile 3 ml Was added dropwise. After completion of the dropwise addition, stirring was continued for 30 minutes at the same temperature, and 0.15 g of 2-amino-5-chloro-3-methylbenzoic acid was added thereto, followed by 0.22 ml of triethylamine. After stirring at 0 ° C for 1.5 hours, 0.064 ml of methanesulfur chloride was further added, and the reaction was allowed to proceed overnight while gradually returning the liquid temperature to room temperature. After completion of the reaction, the reaction solution was extracted by adding ethyl acetate and water. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: n-hexane Z ethyl acetate = 4Zl). 0.15 g of pyridyl) 3 (trifluoromethyl) -1H-pyrazole 5yl] 8 methyl 4H-3,1 benzoxazine 1 4 on was obtained. The NMR spectrum data of this product is as follows

NMR S ppm (Solvent: CDC1 / 300MHz)

 Three

 8.74 (s, lH), 8.68 (d, lH, J = 5.2Hz), 7.99 (d, lH, J = 2.4Hz), 7.55 (d, lH, J = 5.2Hz), 7.52 (s, lH), 7.50 (d, lH, J = 2.4Hz), 1.82 (s, 3H)

 (7) 0.15 ml of triethylamine was gradually added dropwise to a mixed solution of 0.064 g of 1-cyclopropylethylamine hydrochloride and 2 ml of tetrahydrofuran, followed by stirring at room temperature for 1 hour. There, 6 Black mouth 2— [1— (4— Black mouth 3 Pyridinole) 1 3 (Trifunoleolomethinole) 1 1H-Vilasol-5-yl] -8-Methyl-4H— 3, 1 A mixture of benzoxazine-4-one 0.077 g and tetrahydrofuran 2 ml 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 removed under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane Z ethyl acetate = 2Zl) to obtain 0.090 g of the desired product having a melting point of 162-164 ° C.

Next, representative examples of the compounds of the present invention represented by the formula (I) are shown in Table 1, and their physical properties are shown in Table 2. These compounds can be synthesized based on the above synthesis examples or various production methods of the above-described compounds of the present invention. In Table 1, No. indicates the compound No., and the position indicates the position at which pyrazole is bonded to the carbocycle. In Table 1, A1 is -CH- [c-Pr], A2 is -CH (Me)-[c-Pr], A3 is -C

 2

 H-[c-Pr (2-Me)], A4 is -CH- [c-Pr (2,2-CI-1-Me)], A5 is -CH- [c-Pr (l-Me) )]

2 2 2 2

A6—CH (Me) — [c—Bu], A7—CH (Me) —CH SCHF, A8— (CH) —SCHF

 2 2 2 2 2

, A9 — (CH) — SOCHF, A10 — (CH) —SO CHF, Al l — CH CH (Me) — SCH

 2 2 2 2 2 2 2 2

F, A12—CHO, A13—CH— [c—Pr (2—CF)], A14—CH (Me) —CH SCH C

2 2 3 2 2

F and A15 each represent —CO—CH═CH. In Table 1, Me is methyl group, c-Pr is

3 2

A chloropropyl 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 A 4-pyridyl group substituted with a chlorine atom at the 3-position and 5-position of the pyridyl group is shown, and other similar descriptions also apply to this.

[table 1]

Z98STC / 900Zdf / X3d ζε ..80Z0 / .00Z OAV Table 1 (continued)

3] Table 1 (continued)

Four] Table 1 (continued)

Five] Table 2

Next, test examples are described.

Test example 1 Effectiveness test for Lotus monto

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 wet filter paper was laid on a petri dish with a diameter of 9 cm, and an air-dried piece of cabbage was placed on top of it. To that end, we released 10 larvae of 2 to 3 years old, and capped them and left them in a constant temperature room at 25 ° C. On the 5th day after the release, the mortality was determined and the mortality rate was calculated by the following formula. Abnormal insects were also considered dead. Compound Nos. 1 to 10, 12 to 26, 28 to 30, 32, 34, 40, 81, 119, 121, 130, 131, and 133 to 149 This compound showed a high control effect of 90% or more. Death rate (%) = (Number of dead insects Z Number of dead insects) X loo

 [0086] Test Example 2 Effect test on silver leaf whitefly

 Silver leaf whitefly adults were allowed to lay eggs for about 8 to 24 hours in a pot-planted cucumber with one leaf left and the other leaves removed. After that, it was left in a constant temperature room at 25 ° C for 7-10 days. After investigating the number of hatched larvae, the chemical solution prepared so that the concentration of the compound of the present invention was 50 ppm was sprayed at a ratio of about 3 ml Z strain and air-dried. After the treatment, the sample was left in a constant temperature room at 25 ° C for 10 to 14 days. Then, the number of old larvae and the number of pupae was examined, and the control value was calculated by the following formula. 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. High control effect was shown.

 Control value (%) = (1— ((Ta X Cb) / (Tb X Ca))) X 100

 Ta: Number of old larvae after treatment in the treatment area + number of pupae

 Tb: Number of hatching larvae before treatment in the treated area

 Ca: Number of old larvae + number of pupae after treatment in untreated section

 Cb: Number of hatched larvae before treatment in the untreated area

[0087] Test Example 3 Effect test on termites

 A filter paper was placed in a glass petri dish having a diameter of 9 cm, and treated with 1 ml of a chemical solution prepared so that the concentration of the compound of the present invention was 500 ppm. After that, we released 10 termite worker ants and 1 soldier ant, covered them, and left them in a constant temperature room at 25 ° C. Six days after the treatment, the number of ant mortality was investigated, and the death rate was calculated using the following formula. Abnormal insects were also considered dead. When the mortality was determined for the compounds No. 1, 6 and 8, all the compounds showed a high control effect of 80% or more.

 Death rate (%) = (Number of dead worms Z10) X 100

[0088] Test Example 4 Medicinal efficacy test against Phytophthora tick

On the inner surface of a 9 cm diameter petri dish, 1 ml of an acetone solution of the compound of the present invention (concentration: 10 gZml) is dropped with a micropipette. After the inside of the petri dish has dried, put about 100 juvenile ticks and cover with a polyethylene sheet. When the number of tickling (knockdown) ticks after drug contact is observed, the compound of the present invention rolls over most of the ticklet tick. [0089] Test Example 5 Drug efficacy test against cat fleas

0.5 ml of an acetone solution of the compound of the present invention prepared at 5.3 ppm is dropped into a glass tube (inner diameter 2.6 cm, bottom area 5.3 cm ² , height 12 cm) having a smooth bottom surface. Acetone is evaporated at room temperature to form a dry film containing the compound of the present invention on the bottom surface. When 10 cat fleas (Cte nocephalides felis) adults (non-blood-sucking adults within 5 days after emergence) were placed and the compounds of the present invention were exposed, most of the cat fleas showed high control effects.

 [0090] Next, formulation examples are described.

 Formulation Example 1

 (1) Invention compound I

 (2) Clay 72 parts by weight

 (3) Ligated sulfonic acid soda

 The above is uniformly mixed to obtain a wettable powder.

 Formulation Example 2

 (1) Invention compound I

 (2) Talc

 The above is uniformly mixed to form a powder.

 Formulation Example 3

 (1) Compound of the present invention

 (2) Ν, Ν-dimethylacetamide part

 (3) Polyoxyethylene alkyl ether 10fold:!

 (4) xylene 50!

 The above is uniformly mixed and dissolved to obtain an emulsion.

 [0091] Formulation Example 4

 (1) 68 parts by weight of clay

 (2) 2 parts by weight of sodium lignin sulfonate

 (3) Polyoxyethylene alkyl aryl sulfate 5 layers

 (4) Fine silica 25 parts by weight

A mixture of the above components and the compound of the present invention are mixed at a weight ratio of 4: 1 to obtain a wettable powder. The

Formulation Example 5

 (1) 50 parts by weight of the compound of the present invention

 (2) Oxidated polyalkylphenyl phosphate triethanolamine

 2 parts by weight

 (3) Silicone 0.2 parts by weight

 (4) Water 47.8 parts by weight

 In addition to the stock solution uniformly mixed and crushed

 (5) Sodium polycarboxylate 5 parts by weight

 (6) Anhydrous sodium sulfate 42.8 parts by weight

 And uniformly mixed, granulated, and dried to obtain a wettable powder.

Formulation Example 6

 (1) 5 parts by weight of the compound of the present invention

 (2) 1 part by weight of polyoxyethylene octyl ether

 (3) Polyoxyethylene phosphate ester 0.1 parts by weight

 (4) Granular calcium carbonate 93.9 parts by weight

 Mix (1) to (3) uniformly in advance, dilute with an appropriate amount of acetone, and spray onto (4) to remove the acetone and make granules.

Formulation Example 7

 (1) 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

 The above is mixed and dissolved uniformly to make a ultra low volume formulation.

Formulation Example 8

 (1) 40 parts by weight of the compound of the present invention

(2) Oxidated polyalkylphenyl phosphate triethanolamine (3) Silicone 0.2 parts by weight

 (4) Xanthan Gum 0.1 parts by weight

 (5) 5 parts by weight of ethylene glycol

 (6) 52.7 parts by weight of water

 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 ingredients are mixed uniformly to form a solution.

Industrial applicability

 The novel anthranilamide compound of the present invention has a very low control amount and has a very high control effect against pests. For example, it controls various pests that are problematic in the field of agriculture and horticulture and pests that are parasitic on animals It can be widely used as a pest control agent. It should be noted that the entire contents of the specification, claims, drawings and abstract of Japanese Patent Application No. 2005-234214 filed on August 12, 2005 are cited here as disclosure of the specification of the present invention. Incorporate.

Claims

Claims Formula (I) wherein A is alkyl substituted with Y or carbo substituted with D, Q may be substituted with R5, substituted with 3-pyridyl or R5 4-Pyridyl, R1 is halogen, alkyl optionally substituted with X, alkaryl optionally substituted with X, alkyl optionally substituted with X, hydroxy, X An optionally substituted alkoxy, formyl, an alkyl carbonyl optionally substituted with X, carboxyl, an alkoxy carbonyl optionally substituted with X, an alkyl sulfate optionally substituted with X, Alkylsulfuryl which may be substituted, alkylsulfol which may be substituted with X, may be substituted with X !, alkylsulfuroxy, may be substituted with X !, alkylsulfuroxyl , Alkylsulfo-luo optionally substituted with X Ci, amino-containing alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxyiminoalkyl optionally substituted with halogen, cyano or -tro, R2 and R5 are each halogen, X Alkyl which may be substituted, alkoxy which may be substituted with X, alkylsulfuric which may be substituted with X, alkylsulfuric which may be substituted with X, alkylsulfo which may be substituted with X -Alkyl, alkyl sulferoxy optionally substituted with X, alkylsulfieroxy optionally substituted with X, alkylsulfoloxy optionally substituted with X, amino-substituted alkylamino, dialkylamino, formal Mil, cyan or -toro, R3 and R4 are each a hydrogen atom or alkyl, and X is a halogen. Y is an alkoxy optionally substituted with halogen, an alkylsulfuryl optionally substituted with halogen, an alkylsulfuriel optionally substituted with halogen, an alkylsulfol optionally substituted with halogen, or cyan. Group power consisting of halogen, alkyl and haloalkyl may be substituted with at least one selected substituent C 3-4 Roanorequinole; Noroanorequinoles Norefuenore; Nooanorequinoles Norefininore or Noo Roanolequinolesulfol, D is an optionally substituted alkyl, substituted with halogen, alkalkoxy, substituted with halogen, substituted with alkyl or halogen A good alkyloxyl, m is an integer from 0 to 4 and n is an integer from 1 to 2) Bromide compounds, their N- Okishido or a salt thereof. (Wherein A is alkyl substituted with Y or carbo substituted with D, Q may be substituted with IT, 3-pyridyl or R5 !, 4-pyridyl R1 is halogen, alkyl which may be substituted with X, alkyl which may be substituted with X, alkyl which may be substituted with X, hydroxy, alkoxy which may be substituted with X, Formyl, alkyl carbonyl optionally substituted with X, carboxyl, alkoxy carbonyl optionally substituted with X, alkyl sulfonyl optionally substituted with X, alkyl sulfonyl optionally substituted with X Fier, alkylsulfol optionally substituted with X, optionally substituted with X !, alkylsulfuroxy, optionally substituted with X !, alkylsulfieroxy, optionally substituted with X Good alkylsulfo-luoxy, amino Ramino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxyiminoalkyl optionally substituted with halogen, cyano or -tro, and R2 and R5 may be substituted with halogen, X, respectively. A good alkyl, an alkoxy optionally substituted with X, an alkylsulfur optionally substituted with X, an alkylsulfide optionally substituted with X, an alkylsulfole optionally substituted with X, X Alkylsulfuroxy, which may be substituted with X, Alkylsulferoxy, which may be substituted with X, Alkylsulfo-oxy, which may be substituted with X, Amylated alkylamino, Dialkylamino, Formyl, Siano or -Toro, R3 and R4 are each a hydrogen atom or alkyl, and X is substituted with halogen or halogen. Alkyl which may be substituted with alkyl, alkylsulfur which may be substituted with halogen, alkylsulfuryl which may be substituted with halogen, alkylsulfol which may be substituted with halogen or cyano, Y is halogen, alkyl And C3-4 cycloanolequinole; haloanorequinoles norefurenore; haloanorequinolesnorefininore or haloanoresulfol which may be substituted with at least one substituent selected from haloalkyl, and D is an alkyl which may be substituted with a halogen, an alkyl which may be substituted with a halogen, an alkyloxy, which may be substituted with a halogen !, an alkyloxy which may be substituted with an alkyl or a halogen; M is an integer of 0 to 4, n is an integer of 1 to 2, and an anthracamide compound represented by N— A Kishido or manufacturing method of a salt thereof,

Equation (1) (Π):

[Chemical 3]

(Wherein A, R \ R ³ , R ⁴ and m are as defined above), and a compound of formula (III)

(Wherein Q, R ² and n are as defined above, Z is a chlorine atom, —OH or C alkoxy

 1-4) or a compound represented by

(2) Formula (IV): [Chemical 5]

(Wherein, Q, R \ R ² m and n are as defined above) and the formula (V): A—N HR ⁴ (where A and R ⁴ are as defined above) Or a compound represented by (3) Formula (1-2):

[Chemical 6]

^{(Wherein, A, R 3, R 4} , m and n are as defined above, Q ¹ is an is 4 may be pyridyl substituted with substituted with may be 3-pin lysyl or R ^5a with R ^5a , R ^la is a fluorine atom, a chlorine atom, a bromine atom, an alkyl which may be substituted with X, an alkyl which may be substituted with X, an alkyl which may be substituted with X, a hydroxy, and a substitution with X Alkoxy, formyl, alkyl carbonyl optionally substituted with X, carboxyl, alkoxy carbonyl optionally substituted with X, alkyl sulfonyl optionally substituted with X, substituted with X Alkylsulfuriel, alkylsulfol optionally substituted with X, optionally substituted with X !, alkylsulfuroxy, optionally substituted with X !, alkylsulfieroxy, An alkylsulfo-luoxy, which may be substituted with X, A substituted alkylamino, dialkylamino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxyiminoalkyl optionally substituted with halogen, cyano or -toro, and R ^2a and R ^5a are each a fluorine atom, chlorine Atom, bromine atom, alkyl optionally substituted with X, alkoxy optionally substituted with, alkylsulfuryl optionally substituted with X, substituted with X Alkylsulfuriel, optionally substituted with alkylsulfol, optionally substituted with X, optionally substituted with alkylsulfuroxy, optionally substituted with X, substituted with alkylsulfuroxy, substituted with X Alkylsulfo-loxy, amide-containing alkylamido-dialkylamino, formyl, cyano or -toro (X is as described above), and U is a bromine atom or iodine atom; React with metal cyanides,

(4) Formula (1-2):

[Chemical 7]

It is reacted with a compound represented by ^{(wherein, A, Q \ R la,} R 2a, RR 4, m, n and U are as defined above), and carbon monoxide, and a hydrogen donor ,

(5) Equation (1-5):

[Chemical 8]

(Wherein, A, R ^3, R m and n are as defined above, or a 4-pyridyl which may be substituted with has been or 3-pyridyl, or R ^5b substituted with R ^5b, R ^lb is Fluorine atom, chlorine atom, fluorine atom, alkyl optionally substituted with X, alkaryl optionally substituted with X, alkyl optionally substituted with X, hydroxy, optionally substituted with X Alkoxy, alkyl carbo optionally substituted with X, carboxyl, alkoxy carbo optionally substituted with X -Alkyl, an alkylsulfuryl optionally substituted with X, an alkylsulfuriel optionally substituted with X, an alkylsulfol optionally substituted with X, an alkylsulfuroxy optionally substituted with X, Alkylsulferoxy which may be substituted with X, alkylsulfo-oxy which may be substituted with X, amide-containing alkylamino, dialkylamino, alkoxyiminoalkyl which may be substituted with halogen, cyano or -tro R ^2b and R ^5b are each halogen, alkyl optionally substituted with X, alkoxy optionally substituted with X, alkylsulfuryl optionally substituted with X, X Alkylsulfuriel optionally substituted with X, alkylsulfol optionally substituted with X, optionally substituted with X, alkylsulfuroxy, substituted with X And a fluorinating agent are reacted with an alkylsulfuroxy, an alkylsulfo-alkyloxy optionally substituted with X, an amide-containing alkylamino, an alkylamido-containing cyano, or -toro. A method characterized by letting go.

 [3] A pest control agent comprising the anthra-amide compound according to claim 1, its N-oxide or a salt thereof as an active ingredient.

[4] An agricultural and horticultural pest control agent comprising the anthra-amide compound according to claim 1, its N-talide oxide or a salt thereof as an active ingredient.

[5] An insecticide, acaricide or nematicide containing the anthra-amide compound according to claim 1, its N-aged oxide or a salt thereof as an active ingredient.

[6] An animal parasite control agent comprising the anthra-amide compound according to claim 1, its N-xoxide or a salt thereof as an active ingredient.

[7] An animal ectoparasite control agent comprising the anthralamide compound according to claim 1, its N-aged oxide or a salt thereof as an active ingredient.

[8] A prophylactic or therapeutic agent for animal diseases caused by parasites, comprising as an active ingredient the anthralamide compound according to claim 1, its N-aged oxide or a salt thereof.

[9] A method for controlling pests by applying an effective amount of the anthralamide-based compound according to claim 1, its N-oxide or its salt.