WO2006080311A1 - Anthranilamide compound, method for producing same and pest control agent containing same - Google Patents

Abstract

Disclosed is a novel pest control agent. Specifically disclosed is an anthranilamide compound represented by the formula (I) below or a salt thereof. (I) (In the formula, R1 represents a halogen, an alkyl or the like; R2 represents a hydrogen atom, a halogen, an alkyl or the like; R3 represents a halogen, an alkyl or the like; A represents an alkyl substituted by Y; Y represents a C3-4 cycloalkyl which may be substituted by at least one substituent selected from the group consisting of halogens, alkyls and haloalkyls; m represents a number of 0-4; and w represents a number of 0-5.)

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, as a substituent corresponding to A in the following formula (I), C

 3-4 Compounds with alkyl substituted with alkyl are described anywhere.

 WO04Z67528 discloses compounds in which pyridyl is substituted at the 1-position of the pyrazole ring. On the other hand, a phenol is substituted at the 1-position of the pyrazole ring of the formula (I) described later, and the chemical structures of the two are different.

[0002] Patent Document 1: International Publication WO01Z70671

 Patent Document 2: 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]

[Wherein, R ¹ is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, trialkylsilylethynyl, hydroxy, alkoxy, haloanoloxy, honoleminore, anorequinole Canoleboninole, haloanorequinolecanoleboninole, force noreboxinole, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cyano, nitro, amino, alkylamino, dialkylamino, even substituted A good phenoxy, an optionally substituted pyridyloxy, an optionally substituted phenoxycarbon or an optionally substituted pyridyloxycarbon, and R ² is a hydrogen atom, halogen, alkyl, haloalkyl, alkoxy , Halo Arco Shi, Shianoarukokishi, alkylsulfonyl O carboxymethyl, a Xia input nitro, Amino, alkylamino or dialkylamino § amino, R ³ is halogen, alkyl, haloalkyl, alkoxy, Ha Roarukokishi, Shianoarukokishi, alkylsulfonyl O alkoxy, A nitro, ami alkylamino or dialkylamino, A is alkyl substituted with Y, Y may be substituted with at least one substituent selected from the group consisting of halogen, alkyl and haloalkyl , C cycloalkyl, m is 0-4, w is 0-5)

 3-4

 The present invention provides an anthracamide compound or a salt thereof, a production method thereof, a pest control agent containing them, and the like.

 [0007] Examples of desirable embodiments of the compound of the present invention are as follows.

(1) In the above formula (I), R ¹ is halogen, alkyl, haloalkyl, alkyl, trialkylsilylether, hydroxy, formyl, carboxyl, alkoxycarbole, aminocarbol, alkylaminocarbol, R ² is a hydrogen atom, halogen, haloalkyl, haloalkoxy or alkylsulfoxy, R ³ is halogen, alkyl, haloalkyl, alkoxy or -tro, and A is substituted with Y Y is C cycloalkyl optionally substituted with at least one substituent selected from the group consisting of halogen, alkyl and haloalkyl, and m is 0-4

 3-4

 Wherein w is 0 to 5, or a salt thereof.

(2) 1 ^ is halogen, alkyl, haloalkyl, alkyl, formyl, carboxyl, alkoxycarbonyl, § amino carbonyl, alkyl amino carbonyl, Shiano or nits port, R ² is a hydrogen atom, halogen, haloalkyl or haloalkoxy The compound or a salt thereof according to the above (1), wherein R ³ is a norogen, alkyl, haloalkyl or -tro.

 (3) The above formula (I) is converted to formula (I a):

[0008] [Chemical 2]

R is a hydrogen atom, halogen, alkyl, haloalkyl, alkyl, haloalkenyl, alkyl, haloalkynyl, hydroxy, alkoxy, nitro-containing amino, or R ¹² and R ¹⁴ are R ¹³ is a hydrogen atom, R ¹³ is a hydrogen atom, halogen, alkyl, haloalkyl, alkyl, trialkylsilyl ether, hydroxy, alkoxy, haloalkoxy, formyl, alkylcarbole, haloalkylcarbole, carboxyl, alkyl Coxoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbol, cyano-substituted nitro, ami-substituted alkylamino, dialkyla-substituted phenoxy, optionally substituted pyridyloxy, substituted Anyway, phenoxycarbon or Conversion to be Yo, pyridyl O propoxycarbonyl - a le, R ² is a hydrogen atom, a halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, shea Anoarukokishi, alkylsulfonyl O carboxymethyl, Shiano, nitro, Amino, alkylamino or R ³¹ is a hydrogen atom, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyanalkoxy, alkylsulfo-oxy, nitro-nitro R ³² and R ³⁴ are hydrogen atoms, R 3 ³ is a hydrogen atom or halogen, R ³⁵ is a hydrogen atom, halogen or alkyl, and A is Y Substituted alkyl, and Y is C cycloalkyl optionally substituted with at least one substituent selected from the group consisting of halogen, alkyl and haloalkyl.

 3-4

 Or a salt thereof.

(4) R ¹¹ is a hydrogen atom, halogen, alkyl, hydroxy, nitro or amino, R ¹² and R ¹⁴ are hydrogen atoms, R ¹³ is a hydrogen atom, halogen, alkyl, haloalkyl, alkyl, trialkyl Silylethynyl, hydroxy, formyl, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbol, cyano or -tro, and R ² is a hydrogen atom, halogen, haloalkyl, haloalkoxy or alkylsulfoxy. R ³¹ is a hydrogen atom, halogen, alkyl, haloalkyl, alkoxy or -tro, R ³² and R ³⁴ are hydrogen atoms, R ³³ is a hydrogen atom or halogen, R ³⁵ is a hydrogen atom, halogen or Alkyl, A is alkyl substituted with C cycloalkyl

 3-4

 The compound or a salt thereof according to (3), wherein

(5) R ¹¹ is halogen or alkyl, R ¹² and R ¹⁴ are hydrogen atoms, R ¹³ is a hydrogen atom, halogen, alkyl, haloalkyl, alkyl, carboxyl, alkoxycarbonyl, aminocarbonyl, R ² is a hydrogen atom, halogen or haloalkyl, R ³¹ is a hydrogen atom, halogen, alkyl, haloalkyl or -tro, and R ³² and R ³⁴ are hydrogen atoms. Wherein R ³³ is a hydrogen atom or a halogen, and R ³⁵ is a hydrogen atom, halogen or alkyl, or the compound or salt thereof according to (3) above.

 (6) The compound or a salt thereof according to (3), wherein A is alkyl substituted with cyclopropyl.

 The invention's effect

 [0010] The pest control agent comprising the novel anthranilamido compound of formula (I) as an active ingredient has a very high control effect against pests at a low dose.

 BEST MODE FOR CARRYING OUT THE INVENTION

[0011] optionally substituted phenoxy in R ¹ , optionally substituted pyridyloxy, optionally substituted For example, the substituents of phenoxycarbol or substituted pyridyloxycarbol include, for example, halogen, alkyl, haloalkyl, hydroxy, alkoxy, haloanalkoxy, anolequinoles norephenol, no, loa Norequinoles Norefuenore, Anolequinores Norefininore, Noroanorequinores Nolefininore, Anolequinores Norehoninore, No, Roanorequinoles Norehoninore, Ciano, Nitro, Ami Alkylamino And dialkylamino. The number of substitutions of these substituents is 1 or 2 or more, and when it is 2 or more, each substituent may be the same or different. Moreover, the position of each substituent may be any position.

 The number of substitutions of substituent Y in A is 1 or 2 or more, and when it is 2 or more, each substituent Y may be the same or different. Further, the substitution position of the substituent Y may be any position. The number of substituents Y in A is preferably 1.

 Of halogen, alkyl or haloalkyl which is a substituent of C cycloalkyl in Y

3-4

The number of substitutions is 1 or 2 or more. When the number is 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.

Examples of the halogen in R ² , R ³ or Y or the halogen as a substituent include each atom of fluorine, chlorine, bromine or iodine. The number of halogens as substituents is 1 or 2 or more. When 2 or more, each halogen may be the same or different. Also, the position of halogen substitution may be the position of displacement.

The alkyl or alkyl moiety in R \ R ² , R ³ , A or Y may be linear or branched! /, Specific examples of which are methyl, ethyl, propyl, isopropyl, butyl, Examples include C-types such as tertiary butinore, pentinore, and hexinore.

 1-6

Specific examples of the alkenyl or alkenyl moiety in R ¹ may be linear or branched. Examples of the alkellyl or alkenyl moiety include bulle, 1-probe, allyl, iso-probe, 1-tuttle, 1, 3—Butageninore, 1 C such as Hexeninore.

 2-6

The alkyl or alkyl moiety in R ¹ may be linear or branched, and specific examples thereof include ethur, 2-butul, 2-pentyl, and 3-hexynyl. And so on. Specific examples of c cycloalkyl or cycloalkyl moiety in Y include cyclopropyl.

3-4

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

 [0013] The salt of the anthracamide compound of the formula (I) includes any one that is agriculturally acceptable, and examples thereof include alkali metal salts such as sodium salt and potassium salt. 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.

 [0014] 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.

 [0015] The anthranilamido compound of the formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) can be produced according to the following reactions [A] to [0] and a usual salt production method. it can.

[0016] [Chemical 3]

 )

[0017] Al

 It is Koxy.

 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, Νethyl-Ν-methylaniline, 1,8 diazabicyclo [5.4.0] 7 undecene, 1,4-diazabicyclo [2.2.2] octane; and normal butyllithium, Alkyllithiums such as tertiary butanol It can be appropriately selected one or more from. 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 reaction [Α] can be carried out in the presence of a solvent if desired when Ζ 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, 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: acetonitol, propio-tolyl, Ν, Ν dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, Ν-methylpyrrolidone Solvents; Esters such as methyl acetate, ethyl acetate, and propyl acetate; and ketones such as acetone, jetyl ketone, methyl ethyl ketone, and methyl isobutyl ketone can be appropriately selected. .

[0019] When Α is a chlorine atom, the reaction [Α] can be carried out usually at 20 to + 60 ° C, preferably 0 to 30 ° C, and the reaction time is usually about 1 to 24 hours, Desirably, the time can be about 2 to 12 hours.

 [0020] The reaction [A] is usually carried out in the presence of a dehydration condensing agent and a solvent when Z is —OH.

 Examples of the dehydrating condensing agent include carbodiimides such as Ν, Ν′-dicyclohexylcarbodiimide, 1,3 diisopropylcarbodiimide, and 1-ethyl 3- (3 dimethylaminopropyl) carbodiimide hydrochloride. In addition, 1,1'-carbo-rubis 1H imidazole, dichloride phosphate ester, jetyl phosphoric acid dart, 1, 3,5-triaza 1,2,4,6 triphosphorin 1,2,4,4 , 6,6 hexachloride, cyanuric chloride, isobutyl chloroformate, chlorosulfol isocyanate, trifluoroacetic anhydride and the like.

[0021] The solvent may be any solvent inert to the reaction. For example, etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene , Dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene, etc .; aromatic hydrocarbons such as benzene, toluene, xylene; , Propio-tolyl, Ν, Ν dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, Ν-methylpyrrolidone, polar aprotic solvents; methyl acetate, ethyl acetate, acetic acid Esters such as propyl; ketones such as acetone, jetyl ketone, methyl ethyl ketone, and methyl isobutyl ketone; and aliphatic hydrocarbons such as pentane, hexane, heptane, octane, and cyclohexane One type or two or more types can be appropriately selected.

[0022] The reaction [Α] can usually be carried out at 20 to + 60 ° C, preferably 0 to 30 ° C, when the moth is ー, and the reaction time is usually about 0.5 to 24 hours. Desirably, it can be about 1 to 12 hours.

 [0023] 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 carbonates such as sodium carbonate and potassium carbonate; alkali metals such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide Alkoxides; and trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6 dimethylpyridine, 4 pyrrolidinopyridine, N-methylmorpholine, Ν , Ν Dimethylaniline, Ν, Ν Jetylaniline, ェ Ethyl Ν -Methyl lin, 1,8 Diazabicyclo [5.4.0] 1-7 Undecene, 1,4-Diazabicyclo [2.2.2] Octanes like tertiary amines From the above, one or more can be selected as appropriate. 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).

[0024] 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, hexame Polar aprotic solvents such as til phosphoric triamide, sulfolane, dimethylacetamide, N-methylpyrrolidone; and alcohols such as methanol, ethanol, propanol, normal butanol, tertiary butanol, etc. Two or more types can be selected as appropriate.

[0025] The reaction [A] is usually 0 to 120 ° C, preferably 5 to 80 ° C when Z is C alkoxy.

 1-4

 The reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours.

[0026] [Chemical 4]

 (D

[0027] R ² , R ³ , A, m and w are as described above.

 The reaction] can usually be performed 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 chlorophenol, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; aromatic hydrocarbons such as benzene, toluene, xylene; pentane, Aliphatic hydrocarbons such as hexane, heptane, octane, cyclohexane; and acetonitrile, propio-tolyl, Ν, Ν-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethyla One or two or more kinds of polar aprotic solvents such as cetamide and メ チ ル -methylpyrrolidone can be appropriately selected.

 The reaction] 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.

[0028] [Chemical 5]

[0029] A, m and w are as described above, and R ^2a is a hydrogen atom, a fluorine atom, a chlorine atom, an odor atom, an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, a cyanalkoxy, an alkylsulfonyloxy, R ^3a is a fluorine atom, a chlorine atom, a bromine atom, an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, a cyanalkoxy, an alkylsulfo-loxy, a cyano-containing nitro, an amino X is an bromine atom or an iodine atom. Examples of the metal cyanide in the reaction [C] include cyanogen copper, zinc cyanide, cyanide. One type or two or more types can be appropriately selected from potassium fluoride 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 (1-1).

 The reaction] can usually be carried out in the presence of a solvent. As the solvent, any solvent inert to the reaction may be used. For example, ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; and acetonitrile, propio-tolyl,適宜, Ν-Dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, Ν-methylpyrrolidone and other polar aprotic solvents, etc. I can do it.

 [0030] The reaction [C] can be carried out in the presence of a palladium catalyst, if desired. As the palladium catalyst, for example, one or more of tetrakistriphenylphosphine palladium and bistriphenylphosphine palladium dichloride can be appropriately selected. The reaction can be carried out in the presence of a metal iodide if desired. As the metal iodide, one or more kinds can be appropriately selected from, for example, copper iodide, zinc iodide, potassium iodide and the like.

 The reaction can be carried out usually at 0 to 150 ° C, preferably 10 to: LOO ° C, and the reaction time can be usually about 0.1 to 24 hours, preferably about 0.5 to 12 hours. .

[0031] [Chemical 6]

[0032] R ^2a , R ^3a , A, m, w and X 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 (1-1).

 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 moles, preferably 1 to 1.5 moles relative to the compound of the formula (1-1).

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

[0033] The reaction [D] can be usually performed in the presence of a solvent. As the solvent, any solvent inert to the reaction may be used.For example, aromatic hydrocarbons such as benzene, toluene, xylene; pentane, hexane, heptane, octane, cyclohexane, etc. Aliphatic hydrocarbons; ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; and acetonitrile, propio-tolyl, Ν, Ν-dimethylformamide, dimethyl sulfoxide, hexamethyl Phosphoric tri One or more kinds can be appropriately selected from polar aprotic solvents such as amide, sulfolane, dimethylacetamide and N-methylpyrrolidone.

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

 [0034] [Chemical 7]

[0035] R ² , RA, m and w are as described above, R ^la is halogen, alkyl, haloalkyl, anorekeninore, haloanorekeninore, anorequininore, haloanorequininore, trianolenoquinoline reethinyl, Hydroxy, alkoxy, haloalkoxy, alkylcarbonyl, haloalkyl force carbonyl, carboxyl, alkoxycarbonyl, haloalkoxycarbon, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cyano, nitro, aminoalkylamino, dialkylamino, An optionally substituted phenoxy, optionally substituted, pyridyloxy, optionally substituted, phenoxycarbon or optionally substituted !, pyridyloxycarbonyl.

Examples of the fluorinating agent in the reaction] include cetylfluoride trifluoride, [bis (2-methoxyethyl) amino] sulfur trifluoride, xenon fluoride, 2,2-difluoro-1,3 dimethylimidazolidine, tetrafluoride. One or more types can be appropriately selected from sulfur fluoride. Fluorine glaze is 1 to 10 moles, preferably 1 to 4 moles relative to the compound of formula (1-4). Double moles can be used.

 [0036] 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, Aromatic hydrocarbons such as silene; halogenated hydrocarbons such as black benzene, dichlorobenzene, dichloromethane, black mouth form, carbon tetrachloride, chlorotrichloromethane, dichloroethane, trichloroethane, and dichloroethylene. And one or more kinds of ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane, 2-methoxyethyl ether, and the like can be appropriately selected. The reaction can be carried out in an inert gas atmosphere if desired. Examples of the inert gas include nitrogen, helium, and argon.

 The reaction can be carried out usually at -78 ° C to 40 ° C, preferably at 40 ° C to 25 ° C, and the reaction time is usually about 2 to 24 hours, preferably about 5 to 15 hours. Can be

[0037] [8]

R 1, R 2, A, m, w and X are as described above, Q is alkyl or trialkylsilyl, L is a chlorine atom, bromine atom or iodine atom, and R ^A is alkyl.

 In the reaction [F], as a method for producing the compound of the formula (1-6), as shown in the above flow, the compound of the formula (1-1), the formula (VI-1), the formula (VI-2) ) Or a compound of formula (VI-3) may be reacted in the presence of a palladium catalyst and a base. For the compound of formula (1-1), the compound of formula (VI-1), the compound of formula (VI-2) or the compound of formula (VI-3) is usually 1.0 to 10 equivalents, preferably 1.0 to Used at a rate of 3.0 equivalents.

In the reaction [F], a solvent can be used in some cases. Any solvent can be used as long as it does not inhibit the progress of this reaction, for example, ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, dichloromethane. Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; aromatic hydrocarbons such as benzene, toluene, xylene; acetonitrile, propio-tolyl, Ν, Ν-dimethylform Polar aprotic solvents such as amide, dimethyl sulfoxide, dimethylacetamide, N-methylpyrrolidone; esters such as methyl acetate, ethyl acetate, propyl acetate; acetone, jetyl ketone, methyl ethyl ketone, methyl isobutyl ketone 1 type or 2 types or more can be appropriately selected from ketones such as: amines such as dimethylamine and triethylamine; and water.

 [0039] Examples of the base used in the reaction [F] include inorganic salts such as sodium carbonate and potassium carbonate; propylamine, butylamine, jetylamine, diisopropylamine, triethylamine, tributylamine, diisopropylethylamine, Examples thereof include organic amines such as pyrrolidine and piperidine, and are usually used in a proportion of 1.0 to 30 equivalents, preferably 1.0 to 15.0 equivalents, relative to the compound of formula (1-1).

 Examples of the palladium catalyst used in the reaction [F] include tetrakistriphenylphosphine palladium, dichlorobis (triphenylphosphine) palladium, palladium acetate-triphenylphosphine, and the like. Used in a ratio of 0.001 to 0.1 equivalents. When using a palladium catalyst, 0.001 to 0.1 equivalent to the compound of formula (1-1) in which tertiary phosphine such as triphenylphosphine and tri-(.- tolyl) phosphine may coexist. Used at a rate of

 [0040] In the reaction [F], catalysts that may be used include copper halides such as copper (I) iodide, and ammonium salts such as tetraptylammobromide. The compound (1-1) is used in a proportion of 0.001 to 0.3 equivalent.

 The reaction temperature for reaction (F) is usually 0 ° C to 150 ° C, preferably 10 ° C to 100 ° C, usually about 0.1 to 72 hours, preferably 0.3 to 24 hours. Can be about.

[0041] [Chemical 9] [G]

[0042] R ² , R ³ , R ^A , A, m, and w are as defined above, and R ^lb is halogen, alkyl, haloalkino, anoreke-nore, haloanoreke-nore, anorequino-nore, noroanore-nore , Hydroxy, anolecoxy, haloanorecoxy, honoreminore, anorequinolecanoleboninole, noroanorequinolecanonolenore, force ruboxyl, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cyano Nitro, amino, alkylamino, dialkylamino, optionally substituted phenoxy, optionally substituted pyridyloxy, optionally substituted phenoxycarbon or optionally substituted pyridyloxycarbonyl.

 [0043] Examples of the fluorine compound in the reaction [G] include inorganic fluorides such as lithium fluoride, sodium fluoride, potassium fluoride, cesium fluoride, silver fluoride, and tetrabutyl ammonium fluoride. 1 type or 2 types or more can be appropriately selected. The fluorine compound can be used in an amount of 1 to 30 times mol, preferably 1 to 15 times mol for the compound of formula (I-7). When an inorganic fluoride is used, a crown ether such as 18-crown 1-ether may be used.

[0044] The reaction [G] can usually be carried out in the presence of a solvent. As the solvent, any solvent inert to the reaction may be used. For example, jetyl ether, butyl ether. Ethers such as monotel, tetrahydrofuran, dioxane and dimethoxyethane; halogenated hydrocarbons such as black benzene, dichlorobenzene, dichloromethane, black mouth form, carbon tetrachloride, dichloroethane, trichloroethane and dichloroethylene; Aromatic hydrocarbons such as benzene, toluene, xylene; and polar aprotic solvents such as acetonitrile, propio-tolyl, Ν, Ν-dimethylformamide, dimethylsulfoxide, dimethylacetamide, Ν-methylpyrrolidone, etc. 1 type or 2 types or more can be appropriately selected.

 [0045] The reaction can usually be carried out at 10 to 150 ° C, preferably 0 to 100 ° C, and the reaction time is usually about 0.1 to 24 hours, preferably about 0.2 to 12 hours. Can do.

[0046] [Chemical 10]

 (1-10)

R ² , R ³ , A, R ^A , m and w are as described above, and R ^le is halogen, alkyl, haloalquinole, anorekeninore, haloanorekeninore, anorequininore, noroanorequininore, trianorequinoresinole lechur , Hydroxy, alkoxy, haloalkoxy, formyl, alkyl carbonyl, haloalkyl carbonyl, carboxyl, aminocarbonyl, alkylamino carbonyl, dialkylaminocarbonyl, nitro-containing nitro, ami-containing alkylamino, dialkyl-amino They are optionally substituted phenoxy, optionally substituted pyridyloxy, optionally substituted phenoxycarbol or optionally substituted pyridyloxycarbol.

 [0048] Examples of the base in the reaction [H] include potassium trimethylsilanolate, lithium thiomethoxide, sodium phenol selenide and the like, and preferably 1 to 30 times mol, preferably the compound of the formula (1-9) 1 to 5 times mol can be used.

 The reaction] can usually be carried out in the presence of a solvent. As the solvent, any solvent inert to the reaction may be used. For example, ethers such as jetyl ether, butyl ether ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; and acetonitrile, propio-tolyl, Ν, Ν-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric One or more kinds can be appropriately selected from polar non-protonic solvents such as triamide, dimethylacetamide, and メ チ ル -methylpyrrolidone.

 [0049] The reaction [Η] can usually be carried out at 0 to 150 ° C, preferably 10 to 100 ° C, and the reaction time is usually about 0.1 to 72 hours, preferably about 0.5 to 48 hours. can do.

[0050] [Chemical 11]

[0051] A, m, and w are as described above, and R is a fluorine atom, a chlorine atom, an alkyl, a halo anoquinolole, a hydroxy, an alkoxy, a haloalkoxy, a honoreminore, an alkyl carbonyl, a noro anorecanole bonenore , Force noreboxinole, anorecoxicanoleboninole, ro, roanorexoxy decanoyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, amidoalkylamido dialkylamido, optionally substituted phenoxy, substituted V, pyridyloxy, substituted, phenoxycarbol or may be substituted !, pyridyloxycarbon, R ^2b is a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl, a haloalkyl, an alkoxy, Haloalkoxy, cyanalkoxy, alkylsulfuroxy, Mi is input alkylamino or dialkylamino § amino, R ^3b is a fluorine atom, a chlorine atom, alkyl, haloalkyl, alkoxy, haloalkoxy, Shianoarukokishi, Arukirusu sulfo - a Ruokishi Ammi input alkylamino or dialkylamino § amino, R ^B is a hydrogen atom or alkyl.

[0052] Reaction [I] is carried out by reacting the compound of formula (1-11) with hydrogen gas in the presence of a catalyst. Examples of catalysts that can be used include noradium carbon, platinum oxide, and Raney nickel. It can be selected appropriately. The catalyst can be used in an amount of 0.001 to 1.0 times, preferably 0.01 to 0.3 times the weight of the compound of formula (1-11).

 Reaction [I] 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 jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, dichloromethane. Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; alcohols such as methanol, ethanol, propanol, normal butanol, tertiary butanol; benzene, toluene, xylene Aromatic hydrocarbons; polar aprotic solvents such as acetonitrile, propiotolyl, Ν, Ν-dimethylformamide, dimethylacetamide, Ν-methylpyrrolidone; such as methyl acetate, ethyl acetate, propyl acetate 1 type or 2 or more types can be suitably selected from such esters; ketones such as acetone, jetyl ketone, methyl ethyl ketone, and methyl isobutyl ketone; acetic acid; and water.

 Reaction [I] can be usually carried out at 0 to 150 ° C, preferably 10 to: L00 ° C, and the reaction time is usually about 0.1 to 72 hours, preferably about 0.5 to 48 hours. Can do.

[Chemical 12]

^{[0054] R \ R 2a,} R 3a, A, m, w and X are as defined above, R ⁴ is hydrogen atom or alkyl.

 Carbon monoxide in the reaction Ci] can be used in an amount of 1 to 200-fold mol, preferably 1 to 50-fold mol based on the compound of the formula (1-1).

Examples of R ⁴ —NH in the reaction (i) include ammonia, methylamine, and ethylamine.

 2

Can be used. R ⁴ —NH is 1 to 50 times mol, preferably 1

 2

 Up to 10 times mol can be used.

 Reaction ω can usually be carried out in the presence of a palladium catalyst. Examples of the palladium catalyst include tetrakistriphenylphosphine palladium, bistriphenylphosphine palladium dichloride, palladium acetate, palladium acetate monotriphosphine, palladium acetate 1,4-bis (diphenylphosphino) butane, palladium chloride, chloride Palladium tritertiary butylphosphine and the like can be mentioned, and one or more can be selected as appropriate. It is used in a proportion of 0.001 to 0.1 equivalents relative to the compound of formula (g 1). When a palladium catalyst is used, tertiary phosphines such as triphenylphosphine and tri- (0-tolyl) phosphine may coexist, and 0.001-0.1 against the compound of formula (1-1) Used in equivalent proportions.

 Examples of the base used in the reaction ω include inorganic bases such as sodium carbonate and potassium carbonate; organic amines such as triethylamine, tributylamine and diisopropylamine. The amount of the compound of formula (1-1) is usually 1.0 to 30 equivalents, desirably 1.0 to 15 equivalents.

[0055] The reaction Ci] can usually be performed in the presence of a solvent. The solvent may be any solvent that is inert to the reaction.For example, aromatic hydrocarbons such as benzene, toluene and xylene; fats such as hexane, heptane, octane and cyclohexane. Hydrocarbons; ethers such as jetinoreethenole, butinoleethinoleethenole, tetrahydrofuran, dioxane, dimethoxyethane; and acetonitrile, propio-tolyl, Ν, Ν-dimethylformamide, dimethylsulfoxide, One or more polar aprotic solvents such as oxamethylphosphoric triamide, sulfolane, dimethylacetamide and メ チ ル -methylpyrrolidone can be appropriately selected. The reaction Ci] can be usually carried out at 0 to 150 ° C, preferably 10 to: LOO ° C, and the reaction time is usually about 0.1 to 24 hours, preferably about 0.5 to 12 hours. it can.

[Chemical 13]

[]

RR ² R ^3a A, m, w and X are as described above, and R ⁵ is alkyl.

 Carbon monoxide in the reaction [K] can be used in an amount of 1 to 200 times mol, preferably 1 to 50 times mol, of the compound of the formula (1-1).

As R ⁵ —OH in the reaction [Κ], for example, methanol, ethanol, propanol, isopropyl alcohol, butanol and the like can be used. R ⁵ —OH can be used in an amount of 1 to 50 times mol, preferably 1 to 10 times mol, of the compound.

Reaction [K] can be normally performed in presence of a palladium catalyst. Examples of the palladium catalyst include tetrakistriphenylphosphine palladium, bistriphenylphosphine, << radium dichloride, palladium acetate, palladium acetate-triphenylphosphine, palladium acetate-1,4-bis (diphenylphosphino). Butane, palladium chloride, palladium chloride-tritertiary butylphosphine, etc. Can. It is used in a proportion of 0.001 to 0.1 equivalent relative to the compound of formula (ii). When a palladium catalyst is used, 0.001 to 0.1 equivalents to the compound of formula (1-1) in which tertiary phosphines such as triphenylphosphine and tri (0-tolyl) phosphine may coexist Used in percentage.

 Examples of the base used in the reaction [κ] include inorganic bases such as sodium carbonate and potassium carbonate; organic amines such as triethylamine, tributylamine and diisopropylamine. The amount of the compound of formula (1-1) is usually 1.0 to 30 equivalents, preferably 1.0 to 15 equivalents.

 [0058] The reaction [ii] can usually be carried out in the presence of a solvent. The solvent may be any solvent inert to the reaction.For example, aromatic hydrocarbons such as benzene, toluene and xylene; aliphatics such as hexane, heptane, octane and cyclohexane Hydrocarbons; ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; and acetonitrile, propio-tolyl, Ν, Ν —dimethylformamide, dimethyl sulfoxide, hexamethylphos One or more kinds can be appropriately selected from polar aprotic solvents such as holic triamide, sulfolane, dimethylacetamide, and メ チ ル -methylpyrrolidone.

 The reaction [Κ] is usually 0 to 150 ° C, preferably 10 to: LOO ° C, and the reaction time is usually about 0.1 to 24 hours, preferably about 0.5 to 12 hours. Can do.

[0059] [Chemical 14]

 (16)

[0060] A, m, and w are as described above, and R is halogen, alkyl, haloalkyl, alkyne nynore, haloanorekeninore, anorequininore, haloanorequininore, trianolenoquinosylinoretininore, hydroxy , Alkoxy, haloalkoxy, formyl, alkylcarbonyl, haloalkylcarbonyl, carboxyl, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cyano, amino, alkylamino, dialkylamino, substituted R may be a hydrogen atom, a halogen atom, an alkyl, a haloalkyl, an alkoxy, an optionally substituted pyridine, an optionally substituted pyridoxy, an optionally substituted !, a phenoxycarbon or an optionally substituted! Haloalkoxy, Shianoarukokishi, alkylsulfonyl O carboxymethyl, Shiano, Amino, alkylamino or dialkylamino § amino, R ^3e is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, Shianoarukokishi, alkylsulfonyl O alkoxy, ShiaIri Ami-containing alkylamino or dialkylamino.

[0061] In the reaction [L], the compound of the formula (1-15) is usually catalytically hydrogenated with a metal catalyst in a hydrogen atmosphere at normal pressure to several atmospheres in the presence of a solvent, or in an acidic solvent. Reduction can be achieved by the action of a metal catalyst. Examples of the metal catalyst include nodium carbon, acid white, and the like. One or more kinds can be appropriately selected from gold, Raney nickel, iron, salt stannic acid, and the like.

 [L] Hydrogen in the reaction can be used in an amount of 1 to 200 times mol, preferably 1 to 50 times mol for the compound of formula (1-15).

 As the solvent, any solvent inert to the reaction may be used, for example, water; acetic acid; ethyl acetate; alcohols such as methanol, ethanol, propanol, normal butanol and tertiary butanol; Ethers such as butyl ether, tetrahydrofuran, dioxane and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene and xylene; and pentane, hexane, heptane, octane and cyclohexane. One or more of these aliphatic hydrocarbons can be appropriately selected.

 The reaction [L] can usually be carried out at −10 to 100 ° C., preferably 0 to 80 ° C. The reaction time is usually about 0.5 to 24 hours, preferably about 2 to 12 hours. it can.

 [0062] The compound of formula (II) or formula (III) of the reaction [A] is a known compound, or can be produced according to known materials. For example, the compound of the formula (II) can be produced according to the method described in Synthesis, 1 980, page 505 or a method similar thereto, and the compound of the formula (III) is described in US 5082949, WO03Z24222. It can be produced according to the methods described in Schemes 9 to 22 or in accordance therewith.

 [0063] The compound of formula (III) includes a novel compound. The compound can be produced, for example, according to the following reaction [M].

[0064] [Chemical 15]

 (K)

[0065] In the above formula, V is halogen.

 The compound of formula (VIII) can be synthesized by allowing an equimolar amount of hydrazine to act on the compound of formula (VII) in the presence of a solvent.

 Any solvent can be used as long as it is inert to the reaction. For example, water; acetic acid; alcohols such as methanol, ethanol, propanol, normal butanol, and tertiary butanol; jetyl ether, butyl Ethers such as ethyl ether, tetrahydrofuran, dioxane and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene and xylene; and pentane, hexane, heptane, octane and cyclohexane One or more of aliphatic hydrocarbons can be selected as appropriate.

 The first step of the reaction [ii] is usually performed in the presence of a base. As the base, one or more kinds can be appropriately selected from potassium carbonate, sodium carbonate, sodium acetate, sodium hydride, sodium alkoxide, sodium thioalkoxide and the like. The amount used is 0.8 to 4 times mol, preferably 1 to 2 times mol for the compound of formula (VII).

[0066] The first step of the reaction [ii] can be usually performed at 0 to 140 ° C, preferably 20 to 100 ° C, The reaction time is usually about 0.5 to 24 hours, preferably about 2 to 12 hours.

 [0067] The second step of the reaction [M] can be performed by allowing a base to act on the compound of the formula (VIII) in the presence of a normal solvent. As the base, for example, one or more kinds can be appropriately selected from potassium carbonate, sodium carbonate, sodium hydride, sodium alkoxide, sodium thioalkoxide and the like. Usually, the base is used in an amount of 0.8 to 4 times mol, preferably 1 to 2 times mol for the compound of formula (VIII).

 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, dimethoxyethane; and acetonitrile, propio-tolyl, Ν One or two or more types can be appropriately selected from polar aprotic solvents such as Ν-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, and Ν-methylpyrrolidone.

[0068] The second step of the reaction [v] can be usually carried out at 0 to 150 ° C, preferably 50 to 110 ° C, and the reaction time is usually about 0.5 to 24 hours, preferably 1 to 12 hours. It can be about hours.

 [0069] The third step of the reaction [M] can usually be carried out by oxidizing the compound of the formula (IX) with an oxidizing agent in the presence of a solvent. The oxidizing agent can be appropriately selected from, for example, power permanganate, sodium chlorite and the like. The oxidizing agent can be used in an amount of 1 to 20 times mol, preferably 2 to 10 times mol for the compound of formula (IX). When sodium chlorite is used as the oxidizing agent, sodium dihydrogen phosphate is used in an amount of 1 to 20 times mol, preferably 2 to 10 times mol, of the compound of formula (IX).

 As the solvent, one or more can be appropriately selected from water, acetonitrile, propiotolyl, acetone and the like. The third step of the reaction [M] can usually be carried out at −10 to 100 ° C., preferably 0 to 80 ° C., and the reaction time is usually about 0.5 to 24 hours, preferably about 2 to 20 hours. It can be.

[0070] The compound of the formula (IV) in the reaction [B] is a known compound, or can be produced according to known materials. For example, the compound of formula (IV) is Org. Prep. Proceed. Int., 199 It can be produced according to the method described in 3 years, 25%, page 585, the method described in schemes 8 to 10 in WO03Z24222, or the like.

[0071] The compound of formula (V) in the reaction [B] includes a novel compound. The compound is Gabrie

Force that can be produced by one method For example, it can be produced according to the following reaction [N].

[0072] [Chemical 16]

[0073] 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 may be substituted with C alkyl such as methyl and ethyl, and C alkyl.

 1 -6 1-6

 Examples include ferrules.

 [0074] In the first step of reaction [N], T is halogen or —OSO G, and M is sodium or

 2

 When is 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, ethers such as diethyl ether, butyl ether, tetrahydrofuran, dioxane and dimethoxyethane; aromatics such as benzene, toluene and xylene. Aromatic hydrocarbons; polar aprotic solvents such as acetonitrile, propio-tolyl, Ν, Ν dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, メ チ ル methylpyrrolidone; and One or more kinds can be appropriately selected from alcohols such as methanol, ethanol, propanol, normal butanol, and tertiary butanol. [0075] In the first step of the reaction [N], T 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.

 [0076] The first step of the reaction [N] is usually a force that can be performed according to the Mitsunobu method when T is -OH and M is a hydrogen atom. It can be carried out using luazodicarboxylate and triphenylphosphine. The dialkylazodicarboxylate and triphenylphosphine can be used in an equimolar amount with respect to the compound of formula (X). Examples of the dialkylazodicarboxylate include jetinoreazodicanoloxylate, diisopropinoreazodicanoloxylate, and the like.

 [0077] 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 dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; and aromatic hydrocarbons such as benzene, toluene, xylene, etc. It can be selected appropriately.

 The first step of the reaction [N] 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, and the reaction time is Usually, about 0.5 to 24 hours, preferably about 1 to 16 hours can be used.

 [0078] The second step of the reaction [N] can usually be performed by decomposing the compound of the formula (XII) using hydrazine in the presence of a solvent. The hydrazine can be usually used in an equimolar amount with respect to the compound of the formula (XII).

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 [N] 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.

 [0079] The compound of the formula (V) can also be produced according to the following reaction [0].

[0080] [Chemical 17]

[O]

[0081] Β is a hydrogen atom or alkyl, J is — ΟΗ or — OG ¹ (G ¹ is an ether residue), n is 1 or 2, and examples of G ¹ include, for example, methyl, ethyl Like C Archi

 Examples thereof include 1-6 and fur optionally substituted with C alkyl.

 1 -6

 [0082] The first step of the reaction [0] 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, etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, dichloromethane, Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; aromatic hydrocarbons such as benzene, toluene, xylene; acetonitryl, propio-tolyl, Ν, ア ミ ド -dimethylformamide , Dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, polar aprotic solvents such as methyl pyrrolidone; methanol, ethanol, propanol, normal butanol, tertiary rib Alcohols such as Nord; and water one or more of such may be appropriately selected.

 The first step of the reaction [0] can usually be carried out 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. can do.

[0083] In the second step of reaction [0], the compound of formula (XV) is usually used in the presence of a solvent using a reducing agent. It can be done more than anything. As the reducing agent, for example, one or more of lithium aluminum hydride and sodium borohydride can be appropriately selected.

 As the solvent in this case, any solvent that is inert to the reaction may be used. Examples include ethers such as jetinoreethenore, butinoreethinoreethenole, tetrahydrofuran, dioxane, and dimethoxyethane. 1 type or 2 types or more can be appropriately selected.

 [0084] In the second step of reaction [0], the compound of formula (XV) is usually reduced by catalytic hydrogenation with a metal catalyst in a hydrogen atmosphere at atmospheric pressure to several atmospheres in the presence of a solvent. be able to. As the metal catalyst, one or more kinds can be appropriately selected from, for example, noradium carbon, platinum oxide, Raney nickel and the like.

 As the solvent in this case, any solvent that is inert to the reaction may be used. For example, water; acetic acid; ethyl acetate; alcohols such as methanol, ethanol, propanol, normal butanol, and tertiary butanol; Ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; halogenated compounds such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene Hydrocarbons; 1 or 2 aromatic hydrocarbons such as benzene, toluene, xylene; and aliphatic hydrocarbons such as pentane, hexane, heptane, otatan, cyclohexane, etc. The above can be selected as appropriate.

 [0085] The second step of the reaction [0] can usually be carried out at −10 to 100 ° C., preferably 0 to 80 ° C., and the reaction time is usually about 0.5 to 24 hours, preferably 2 to It can be about 12 hours.

 The compound of formula (V) can be removed as a salt by adding an acid to the reaction solution in the production process.

 [0086] 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 is, for example, each problematic in the field of agriculture and horticulture. It is particularly useful as a species pest control agent, that is, an agricultural and horticultural pest control agent, or a pest control agent that parasitizes animals, that is, an animal parasite control agent.

 [0087] 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 .; Stored pests such as moss; clothing, house pests such as Iga, Himekatsubushimushi, termites, etc .; effective for the control of indoor dust mites such as Pterodactylidae, Scarlet Mite, Southern Mite . Among them, the agricultural and horticultural harmful organism 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 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, by treating the soil with a pesticide for agricultural and horticultural use containing the compound of the present invention, soil harmful insects, mites, nematodes In addition, it can control pests in the foliage at the same time as the control of gastropods and isopods.

[0088] Another desirable aspect of the pest control agent containing the compound of the present invention is that the above-mentioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. And pesticides for agricultural and horticultural use. 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 adjuvants. 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 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, dimethylacetamide, Ν-methyl-2 — Solvents such as pyrrolidone and alcohol; fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylates, alkylsulfate esters, alkylsulfates, alkylaryl sulfates, alkyldiglycols Ether sulfate , Alcohol sulfate, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignite sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester salt , Alkylaryl phosphate, styryl aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether ether sulfate, polyoxyethylene alkyl ether Anionic surfactants such as phosphates, polyoxyethylene alkylaryl phosphate esters, naphthalene sulfonate formalin condensate salts; sorbitan fatty acid esters, glycerin fatty acid esters, fatty acids LIDALICELIDE, FATTY ACID ALCOHOL POLYDALYL ETHER, ACETYLENE GLYCOL, ACETYLENE ALCOHOL, OXYANOLECYLENE BLOCK POLYMER, POLYoxyethylene Alkyl Ether, Polyoxyethylene Alkyl Reel Ether, Polyoxyethylene Styryl Alyl Ether, Polyoxyethylene Glycol Alkyl ether, polyethylene glycol, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid ester Nonionic surfactants such as tellurium spreading agents; olive oil, kapok oil, castor oil, palm oil, coconut oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, large Examples include bean oil, rapeseed oil, linseed oil, drill oil, liquid oil, vegetable oils and mineral oils. 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 auxiliary agents, they can be appropriately selected from those known in the art. For example, various commonly used adjuvants such as extenders, thickeners, anti-settling agents, antifreeze agents, dispersion stabilizers, safeners, and antifungal agents. The compounding ratio of the compound of the present invention and various adjuvants is 0.001: 99.9 99 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 prescribed concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.

[0090] The application of the agricultural and horticultural pesticide containing the compound of the present invention cannot be generally specified due to differences in weather conditions, formulation, application time, application location, pest type and occurrence, etc. In general, the active ingredient concentration is 0.05 to 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. In addition, application of the agricultural and horticultural pest control agent, which is another preferred embodiment of the pest control agent containing the compound of the present invention, 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.

[0091] Various formulations of the agricultural and horticultural pesticide containing the compound of the present invention, or a diluted product thereof, 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. [0092] In addition, the agricultural and horticultural pesticide containing the compound of the present invention can be used in combination with or combined 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.

 [0093] The mixing ratio of the compound of the present invention and the active ingredient compound of other agricultural chemicals cannot be specified 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.

[0094] 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, Profenofos, Cyclonorevos, Dichlorvos, Fenitrothion, EPN, Diazinon, Chlorpyrif os-methyl, Acephate, Prothiofos , Phosthiazate (Fosth iazate), Phosphocarb (Chosphofos), Cadusafos, Disulfoton (Chlorpyrifos), Demeton-S-methyl, Dimethoate, Dimethoate, Methidophos (Metidophos) Organophosphate compounds such as Parathion; Carbaryl, Propoxur, Aldicarb ), Carboforan, Thiodicarb, Methomyl, Oxamyl, Ethiofencarb, Pirimicarb, Fenobucarb, Carbosulfan, B carbamate compounds such as acarb); nereistoxin derivatives such as Cartap, Thiocyclam, Bensultap;

Organochlorine compounds such as Dicofol, Tetradifon, Endosulfan; Organometallic compounds such as Fenbutatin Oxide; Fenvalerate, Permethrin, Pyrethroid compounds such as Cypermet hrin, Deltamethrin, Cyhalothrin, Tefluthrin, Etofenprox, Fenpropathrin, Bifenthrin; Diflubenzuron, Chlorfluazuron, Teflubenzuron, Flufenoxuron, Lufenuron, Novaluron, Bistrifluron, Noviflumuron Nabenzo Lurea system Juvenile hormone-like compounds such as Methoprene, Pyriproxyfen, Fenoxycarb; Pyridazinone compounds such as Pyridaben; Fenpyroximate, Fipronil, Tebufenpyrad Pyrazole compounds such as Tebufe npyrad, Ethiprole, Tolfenpyrad, Acetoprole, Pyrafluprole, Pyriprole; Imidacloprid, Tenpyram Ni , Acetamiprid, thiacloprid, thiamethoxam, clothiaidin, dinoteforan, and other neo-cotinoids; Tebufenozide, And hydrazine compounds such as dihydro compounds, organosulfur compounds, urea compounds, triazine compounds, and hydrazone compounds. Other compounds include Flonicamid, Buprofezin, Hexythiazox, Amitraz, Chlordimefor m, Silafluofen, Triazamate ), Pymetrozin e, Pyrimidifen, Chlorfenapyr, Ind oxacarb, Acequinocyl, Etoxazole, Cyrom azine, 1,3- (1,3-dichloropropene), Diafenthiur on), Benclothiaz, Flufenerim, Pyridalyl, Spirodiclofen, Bifenazate, Spiromesifen, Propargite, Clofentez, Clofentez Examples of such compounds include Fluacrypyrim, Flubendiamide, Cyflu metofen, 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, minolemectin, Antibiotics such as Spinosad, Ivermectin and Lepimectin; natural products such as Azadirachtin and Rotenone can 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, Triflumizole, Etaconazole, Propiconazole, Penconazole, Penoleazole (Flusilazole), Microbutanol (Myclobutanil), Cyproconazole, Cybuconazole, Terbuconazole, Hexaconazole, Furcon azole-cis, Prochloraz, M, Prochloraz, M Epoxyconazo nore (Epoxiconazole), Atofconan nore (Tetraconazole), Yayoshokonazo Azole compounds such as Oxpocona zole and Sipconazole; Quinoxaline compounds such as Quinomethionate; Maneb, Zineb, Mancozeb, Polycarbamate Dithiocarbamate compounds such as Propineb; Organochlorine compounds such as Fthalide, Chlorothalonil and Quintozene; Benomyl and Thiophanate Methinore -Imidazole compounds such as Methyl, Carbendazim, Cyazofamid; Pyridinamine compounds such as Fluazinam; Cyanoacetamide compounds such as Cymoxanil; Metalaxyl ( Metala xyl), oxadixyl, offorace (Oforace), benalaxyl, furaxyl (Furalaxyl), phenolic compounds such as Cyproforam; sulfenic acids such as dichlofluanid Compounds; Copper-based compounds such as cupric hydroxide and organic copper; Isoxazole-based compounds such as hydroxyisoxazole; Fosety aluminum, Organophosphorous compounds such as Tolclofos-Methyl, S-benzyl Ο, Ο-diisopropyl phosphorothioate, Ο-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate; N-halogenoalkyl compounds such as Captan), Captafol, Folpet; Dicarboximide compounds such as Procymidone, Iprodione and Vinclozolin; benzalide compounds such as Flutolanil, Mepronil and Z oxamide Piperazine compounds such as Triforine; Pyridine compounds such as Pyrifenox; Carbinol compounds such as Fenarimol and Flutriafol; Fenpropi dine ) Piperidine compounds such as Fenpropimorph; Morphine compounds such as Fenpropimorph; Organotin compounds such as Fentin Hydroxide and Fentin Acetate; Pencicuron (Pencycuron) ) Urea compounds such as); Synamic acid compounds such as Dimethomorph Phenol carbamate compounds such as Diethofen carb; Cyanopirol compounds such as Flud ioxonil; Azoxystrobin, Taresoxime methylol ( Streptocylvirin compounds such as Kresoxim- Methyl, Metominofen, Trifloxystrobin, Picoxystrobin, Pyraclostrobin; such as Famoxad one Oxazolidinone compounds; thiazole carboxamide compounds such as ethaboxam; silylamide compounds such as silthiopham; aminoacid amide carbamate compounds such as Iprovalicarb; like Fenamidone Nasty lizard System compound; Hyde port as Kisamido to Fen (Fenhexamid) Kishia - Lido compounds; Furusurufuamido (Flusulfamide) base such as Nze Sulfonamide compounds; atraquinone compounds; crotonic acid compounds; antibiotics. Other compounds include Isoprothiolane, Tricyclazole, Pyroquilon, Diclomezine, Probenazole, Quinoxyfen, Propamocarbole hydrochloride, and Propamocarb Hydrochloride. Examples thereof include spiroxamine, chloropicrin, dazomet, and metam-sodium.

 [0096] Other pesticides that can be used in combination with or combined with the compounds of the present invention include, for example, active compounds of herbicides such as those described in the Farm Chemicals Handbook (2002 edition), particularly those treated with soil. There are things.

 [0097] 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 parasitic on the heart, liver, blood vessels, subcutaneous, lymphoid tissue, etc., but it 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.

[0098] Animal parasitic mites include, for example, Boophilus microplus, Rnipicephalus sanguineus, Haemaphvsalis longicorni s, and Tematani (Haemaphvsalis flava) campanula ta, chair power (Haemaphvsalis concinna), hamatophvsalis iap onica, sinker "Haemaphvsalis ias, mite (Ixodes ovatus, tick) Ticked ticks (Ixodes persulcatus), Takasago Kiraramagini (Amblvomma testudinarium), gifted Togenamatani (Haemaphvsalis megaspinosa), Aminakakumaguji (Dermacentor r eticulatus); Trisanta-(Ornithonvssus svlviarum, Na Trisantani (Ornith avian mites such as onvssus bursa: Eutrombicula wic hmanni, Leptotrombidium akamushi, Leptotrom bidium pallidum., LeDjtotrombidium iuji, Tosat mbidium tosa), European Akida-(Neotrombicula autumnalis), American crest beetle (Eutrombicula alfreddugesi), cave beetle such as Helenicula mivagawai: Larvae such as (Chevletiella blakei); Psoroptes cuniculi, Chorioptes bovis, Otodectes cvnotis, Sarcoptes scabiei, cattle Hymenids: Nibibididae such as Demodex canis. Among them, the animal parasite control agent containing the compound of the present invention is particularly effective for controlling ticks and the like.

[0099] As fleas, for example, ectoparasite worms belonging to the order Flea (Siphonaotera), more specifically fleas belonging to the family Flea (Pulicidae), Nagano (CerateDhyllus), etc. . Examples of fleas belonging to the family Fleas include: Fleafish (CtenoceDhalides canis), Nekono (CtenoceDhalides felis), Humanfish (Pulex irritans), Nite trout flea (Echidnoph aga gallinacea), Examples include fleas (Leptopsvl la seenis), yosokuchinonosuno (Nosopsyllus fasciatus), and Yamatonezuno (Monopsvll us ank). Among them, the animal parasite control agent containing the compound of the present invention is effective for controlling fleas belonging to the family flea family, especially cynomolgus, cat flea and the like.

[0100] 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 Thometgebu Diptera pests. Examples of endophytic organisms include nematodes such as lungworms, bench beetles, tuberous worms, gastric parasites, roundworms, and filamentous worms; Crustacea, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms; Japanese schistosomiasis, fluke-like fluke; kokujimu, malaria parasite, intestinal floriformus, toxoplasma Protozoa such as Cryptosporidium.

 [0101] Examples of host animals include various pets, livestock, poultry, and the like.

, Inu, Cat, Mouse, Rat, Hamster, Guinea pig, Squirrel, Usagi, Ferret, Bird (eg, Pigeon, Worm, Nine-bird, Bird of Bird, Parakeet, Giant Pinus, Canary, etc.), Usi, Horse, Bud Tae, Hidge, Ducks, -Toritori 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.

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, liquids, emulsions, aqueous suspensions together with appropriate auxiliary agents. In addition, it can be used in various forms such as 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, dimethylacetamide, dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol , Benzenoreanoleconole, Ethylene glycol, Propylene glycol, Polyethylene glycol, Liquid polyoxyethylene glycol nore, Butinoresin glycol nore, Ethylene glycol nole monomethinoatenore, Ethyleneglycoleno monoethylenoatenore, Diethylene glycol Solvents such as ricinole monoethylenoate, diethylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; butylhydroxyl-sol, butyhydroxytoluene, ascorbic acid, sodium metabisulfite, Anti-oxidizing agents such as propyl gallate and sodium thiosulfate; film forming agents such as polybulurpyrrolidone, polybular alcohol, and a copolymer of buryl acetate and burpyrrolidone; the agricultural and horticultural pest control agents described above And vegetable oils and mineral oils exemplified as supplements for pharmaceutical preparations; lactose, sucrose, glucose, starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other carriers such as commercially available feed ingredients. Each component of these adjuvants can be used by appropriately selecting one or more types without departing from the object of the present invention. In addition to the above-mentioned adjuvants, they can be used by appropriately selecting from those known in the field, and moreover, various adjuvants used in the above-mentioned agricultural and horticultural fields as appropriate. You can also select and use.

 [0103] The compounding ratio of the compound of the present invention to 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.

 [0104] The compound of the present invention is administered to the host animal 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.

 [0105] 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 generally O.Olmg to: L00g relative 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 includes a prophylactic or therapeutic agent for parasite-derived animal diseases comprising the compound of the present invention as an active ingredient, and a method for preventing or treating parasite-derived animal diseases.

[0106] When the compound of the present invention is used as an animal parasite control agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretic agents, sedatives, anti-inflammatory agents, 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. Can be one in this case The layer may show an excellent effect. 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 Methyl phenol] 1— (2 Black mouth phenol) 3 (Trifluoromethyl) 1H Pyrazole 5 Synthesis of Luboxamide (Compound No. 10 below)

 To a mixed solution of 0.24 g of 1-cyclopropylethylamine hydrochloride and 5 ml of tetrahydrofuran, 0.40 g of triethylamine was gradually added dropwise, followed by stirring at room temperature for 1 hour. There, 6 chloro 1- [1— (2 black mouth phenol) 3 (trifluoromethyl) 1H pyrazole 5 -yl] 8 methyl 4H— 3, 1 benzoxazine 4 on 0.30 g and tetrahydro mouth furan 5 ml of the mixture was gradually added dropwise. After completion of dropping, the mixture was reacted under reflux for 1 hour. 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-xan Z-ethyl acetate = 9Z 1 8 Z2) to obtain 0.09 g of the desired product having a melting point of 226 228 ° C.

[0108] Synthesis Example 2

 1— (2—Black mouth) N— [2— [[(1-Cyclopropylethyl) amino] carbol] -4-formyl-6 methylphenol] 3 (trifluoromethyl) 1H Synthesis of pyrazole 5-carboxamide (Compound No. 14 below)

1— (2 Black mouth) N— [2— [[(1-Cyclopropylethyl) amino] carbol] — 4 Rhodo 6-methylphenol] 3 (Trifluoromethyl) 1H Pyrazole 5 —Tetrakistriphenylphosphine palladium (0.06 g) was placed in a mixed solution of carboxamide (0.71 g) and tetrahydrofuran (10 ml), and the atmosphere in the flask was changed to a carbon monoxide atmosphere. There, the reaction was carried out while gradually dropping a mixed solution of 0.36 g of tributyltin hydride and 30 ml of tetrahydrofuran over 3.5 hours under reflux. After completion of the reaction, dilute the reaction solution with 50 ml of ether. After adding 50 ml of saturated aqueous potassium fluoride solution, the mixture was stirred overnight. The organic layer was separated, washed with water and saturated brine, and dried over anhydrous sodium 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 = 1Z0-: LZD to obtain 0.29 g of the desired product having a melting point of 169 ° C. .

[0109] Synthesis Example 3

 N— [2 Black mouth 6] [[(1 Cyclopropylethyl) amino] carbol]-4—Edophenol 1— (2 Black mouth) 3 (Trifluoromethyl) 1H Pyrazole Synthesis of 5-force ruboxamide (Compound No. 19 below)

 To a mixed solution of 0.69 g of 1-cyclopropylethylamine hydrochloride and 5 ml of tetrahydrofuran, triethylamine l.Og was gradually added dropwise under ice cooling, followed by stirring at room temperature for 1 hour. There, 8 Chromium 1 2- [1— (2 Chromium Methyl) 3 (Trifluoromethyl) 1H Pyrazolu 5—yl] -6 Codo 4H— 3,1—Benzoxazine 4 on l. A mixed solution of Og and tetrahydrofuran 5 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, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane Z ethyl acetate = 1 Z0 to 3Z 1) to obtain 0.93 g of the desired product having a melting point of 170 ° C. Got.

[0110] Synthesis Example 4

 N— [2 Black mouth 4 Cyan 6 — [[(1 Cyclopropylethyl) amino] Carbool] 1— (2 Black mouth phenol) 3 (Trifluoromethyl) 1H Pyrazole 5 Synthesis of Ruboxamide (Compound No. 20 below)

N— [2 Black mouth 1] 6- [[(1 Cyclopropylethyl) amino] carbo] 4 [Chodophor] 1— (2 Black mouth) 3 (Trifluoromethyl) 1H Pyrazole 5 — A mixture of 0.10 g of carboxamide and 2 ml of tetrahydrofuran was charged with 0.017 g of cuprous iodide, 0.022 g of tetrakistriphenylphosphine palladium and 0.16 g of cuprous cyanide. The mixture was reacted under reflux for 2.5 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 brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: n-hexane Z ethyl acetate = 1Z0-1 Purification by ZD gave 0.058 g of the desired product having a melting point of 165 to 167 ° C.

[0111] Synthesis Example 5

 1— (2—Black mouth phenyl) N— [2— [[(1-Cyclopropylethyl) amino] carbol] -4 difluoromethyl 6 methylphenyl] 3 (trifluoromethyl) -1H-pyrazo Synthesis of roux 5-carboxamide (compound No. 39 below)

 1— (2—Black mouth) N— [2— [[(1-Cyclopropylethyl) amino] carbol] — 4 Formyl-6 methylphenol] 3 (Trifluoromethyl) 1H Pyrazole A mixture of 5-carboxamide 0.15 g and dichloromethane 5 ml was cooled to 78 ° C. in an acetone-dry ice bath. Thereto, 0.19 g of cetylaminosulfur trifluoride was gradually added dropwise, and the temperature was raised to room temperature over 4 hours, followed by reaction for 6 hours. After completion of the reaction, the reaction solution was gradually added to ice water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium 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 = 1Z0-3Z1) to obtain 0.12 g of the desired product with a melting point of 165 ° C. It was.

[0112] Synthesis Example 6

 1— (2—Black mouth) N— [2— [[(1-Cyclopropylethyl) amino] carbol]-4 Methoxycarbonyl 6 methylphenyl] 3 (Trifluoromethyl)-1H -Vilazol-5 Carboxamide (Compound No. 40)

 1— (2 Black mouth) N— [2— [[(1-Cyclopropylethyl) amino] carbol] — 4 Rhodo 6-methylphenol] 3 (Trifluoromethyl) 1H Pyrazole 5 To a mixed solution of carboxamide 0.42 g, dimethyl sulfoxide 10 ml, methanol 2 ml, triethylamine 0.5 ml, palladium acetate 0.05 g and 1,4-bis (diphenylphosphino) butane O.lg are added, and the inside of the flask is mixed with monoacid. After changing to a carbon atmosphere, it reacted at 70 ° C for 2.5 hours. The reaction mixture was added to water and extracted with ether. The organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n-hexane Z ethyl acetate = 8Z2-6Z4) to obtain 0.24 g of the desired product having a melting point of 178-180 ° C. It was.

[0113] Synthesis Example 7 4 -Force Nolevoxinole 1— (2—Black mouth phenyl) N— [2— [[((1 Cyclopropylethyl) amino] carbol]-6 Methylphenol] 3 (Trifluoromethyl) 1H Pyrazol Synthesis of roux 5 carboxamide (compound No. 42 below)

 1— (2—Black mouth) N— [2— [[(1—Cyclopropylethyl) amino] carbol] — 4 Methoxycarboru 6 Methylphenol] 3 (Trifluoromethyl) A mixture of 1H pyrazole-5 carboxamide Ol lg and 5 ml of tetrahydrofuran was added to a mixture of 0.10 g of potassium trimethylsilanolate and 5 ml of tetrahydrofuran at room temperature, and the mixture was stirred at room temperature for 2 days. Water and aqueous sodium hydroxide solution were added, and the mixture was extracted with ethyl acetate. The aqueous layer was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the precipitated crystals were washed with hexane to obtain 0.05 g of the desired product having a melting point of 227 to 232 ° C.

[0114] Synthesis Example 8

 1— (2—Black mouth) N— [2— [[(1-Cyclopropylethyl) amino] carbole] -6-methyl-4- (2-trimethylsilylethyl) — 3— (Trifluoromethyl) 1H Pyrazole-5 Carboxamide (Compound No. 184)

 1— (2—Black mouth) N— [2— [[(1—Cyclopropylethyl) amino] carbol] — 4 Rhodo 6-methyl phenol] 3 (Trifluoromethyl) 1H Pyrazole 5-Carboxamide 1. Add 0.24 g of trimethylsilylacetylene, 3 ml of triethylamine, and 56 mg of bis (triphenylphosphine) palladium (II) to 10 ml of tetrahydrofuran and stir for 10 minutes. 60 mg of copper was added. The mixture was reacted at room temperature for 30 minutes. 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 Z ethyl acetate = 9Z 1-7Z3) to obtain 0.93 g of the desired product having a melting point of 278-281 ° C.

[0115] Synthesis Example 9

 1— (2—Black mouth) N— [2— [[(1-Cyclopropylethyl) amino] carbol]-4 -Ethur-6 Methylphenol] 3 (Trifluoromethyl) 1H Synthesis of pyrazole 5 —carboxamide (Compound No. 185 below)

1— (2—Black mouth) N— [2— [[(1-Cyclopropylethyl) amino] carbol] —6—Methyl—4— (2-trimethylsilylethyl) phenol] — 3— (trifluoromethyl) -1H pyrazole-5 carboxamide 0. 86 g and dimethoxyethane 10 ml in a mixture of potassium fluoride 87 mg, 18 mg of Crown 1-6 was stirred at room temperature for 2 hours. In addition, 1.5 ml of a 1M tetrahydrofuran solution of tetraptyl ammonium fluoride was added to the reaction solution and reacted for 5 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane Z ethyl acetate = 8Z 2-0Zl) to obtain 0.18 g of the desired product having a melting point of 234-238 ° C.

[0116] Synthesis Example 10

 1— (2—Black mouth) N— [2— [[(1—Cyclopropylethyl) amino] carbol] -4-ethyl 6 methylphenol] 3 (trifluoromethyl) 1H pyrazole 5-—Synthesis of carboxamide (Compound No. 186)

 1— (2—Black mouth) N— [2— [[(1—Cyclopropylethyl) amino] carbol] — 4 Etul-6 methylphenyl] 3 (Trifluoromethyl) -1H-pyrazole A mixture of —5-carboxamide 0.1 l lg and 10% palladium-carbon 0.03 g and ethyl acetate 20 ml was stirred at room temperature for 2.5 hours under a hydrogen atmosphere. The reaction solution was filtered through Celite, and the filtrate was concentrated to obtain 0.10 g of the desired product having a melting point of 193-195 ° C.

[0117] Synthesis Example 11

 N— [4 Aminocarbole 2— [[(1 Cyclopropylethyl) amino] carbole]-6 —Methylphenol] 1— (2—Clorophenyl) 3 (Trifluoromethyl) 1H Pyrazo Iru 5 Synthesis of carboxamide (compound No. 85)

1— (2 Black mouth) N— [2— [[(1-Cyclopropylethyl) amino] carbol] — 4 Rhodo 6-methylphenol] 3 (Trifluoromethyl) 1H Pyrazole 5 — Add 0.08 g of palladium acetate and 1,4-bis (diphenylphosphino) butane O.lg to 6 ml of (1: 1) mixed solution of carboxamide 0.3 g and dimethyl sulfoxide and triethylamine. A carbon oxide atmosphere was used. To this was added dropwise 8 ml of a 0.5 M dioxane solution of ammonia, and then heated to 80 ° C. After stirring for 1 hour, the reaction solution was added to water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. solvent Was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane Z ethyl acetate = lZl to OZl) to obtain 0.02 g of the desired product having a melting point of 159 ° C.

[0118] Synthesis Example 12

 N— [2 amino 6 — [[(1 cyclopropylethyl) amino] carbol] phenol] 1—phenol 3 (trifluoromethyl) 1 H pyrazole 5 carboxamide (compound no. 195)

 N— [2— [[(1 Cyclopropylethyl) amino] carbol]-6 Nitrophenyl] 1— (2—Clorophenyl) 3 (trifluoromethyl)-1H-pyrazole 5 Carboxamide 0.13 g Then, 0.5 g of 5% palladium-carbon was placed in a mixed solution of 10 ml of methanol and the inside of the flask was replaced with hydrogen. After stirring at room temperature for 20 hours, the nodium-carbon was suction filtered through celite. The filtrate was washed with methanol and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane Z ethyl acetate = 3/1 to 0Z 1) to obtain 0.06 g of the desired product having a melting point of 23 C.

[0119] Reference Example 1

 Synthesis of N- (1-cyclopropylethyl) -3-methyl-2-trobenzamide

 0.54 g of triethylamine is gradually added dropwise to a mixture of 0.41 g of 1-cyclopropylethylamine hydrochloride and 5 ml of tetrahydrofuran, and then stirred for 35 minutes at room temperature. Benzoyl chloride (prepared in the following way: 3-methyl-2-trobenzoic acid 0.5 g and methylene chloride 6 ml in a mixed solution of 0.7 ml of sodium oxalyl and 2 drops of dimethylformamide at room temperature 1 After stirring for 5 hours, a mixture of 5 ml of tetrahydrofuran and 5 ml of tetrahydrofuran was added dropwise under ice-cooling. After reacting for 30 minutes under ice cooling, the reaction was performed for 30 minutes at room temperature. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium 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 = 8Z2-6Z4), mp 125-127. 0.40 g of the target product of C was obtained.

[0120] Reference Example 2

Synthesis of 2-amino-N- (1-cyclopropylethyl) -3-methylbenzamide Add 0.12 g of 10% palladium on carbon to a mixture of 0.66 g of N— (1-cyclopropylethyl) -3-methyl-2-trobensamide and 12 ml of ethanol, and place the flask in a hydrogen atmosphere. Reacted for 3 hours. After completion of the reaction, water was added to the reaction solution, followed by Celite filtration, and the cake was washed with ethyl acetate. After concentration under reduced pressure, extraction with ethyl acetate was performed. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane Z ethyl acetate = 8Z2-6Z4) to obtain 0.29 g of the desired product having a melting point of 117-119.

[0121] Reference Example 3

 2 Amino-5 Black mouth N- (1-Cyclopropylethyl) 3-Methylbenzamide synthesis

 2 0.18 g of N chlorosuccinimide was added to a mixed solution of 0.29 g of 2-amino-N- (1-cyclopropylethyl) -3-methylbenzamide and 5 ml of dimethylformamide, and reacted at 90 ° C. for 2 hours. After completion of the reaction, water was added to the reaction solution and stirred for 30 minutes, followed by filtration. The obtained crystals were dissolved in ethyl acetate, dried over anhydrous sodium 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 = 9Zl to 75Z25) to obtain 0.24 g of the desired product having a melting point of 155 to 157 ° C. .

[0122] Reference Example 4

 Synthesis of 1-cyclobutylethylamine hydrochloride

 After adding 9.6 g of hydroxylammonium chloride and 6.3 g of sodium carbonate to 40 ml of an aqueous solution of 10 g of cycloptylmethylketone, the mixture was refluxed for 4 hours. After cooling, the mixture was extracted with ether. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 11.5 g of crude cyclobutylmethyloxime.

Under a nitrogen atmosphere, 6.8 g of lithium aluminum hydride and 80 ml of anhydrous ether were added to a 500 ml triple flask equipped with a reflux tube and a dropping funnel. To this was slowly added dropwise a mixed solution of 11.5 g of crude cyclobutylmethyloxime and 50 ml of ether. After the dropwise addition, the mixture was refluxed for 7 hours. 300 ml of ether was added to the reaction mixture and cooled to 0 ° C. After mounting the dry ice capacitor, a 20% aqueous sodium hydroxide solution was slowly added dropwise. After dripping, the mixture was stirred for 1 hour, and the precipitate was suction filtered. The organic layer was separated and the aqueous layer was extracted with ether. Yes The machine layer was washed with saturated brine, 15 ml of concentrated hydrochloric acid was added, and the solvent was distilled off under reduced pressure. The precipitated crystals were washed with acetonitrile, suction filtered and dried to obtain 7.8 g of 1-cyclobutylethylamine hydrochloride.

[0123] Reference Example 5

 1- (2 Black mouth 6 Nitrophenol) 3 (Trifluoromethyl) 1H Pyrazole 5

 1st process

 Synthesis of 5- (furan-2-yl) 3 (trifluoromethyl) 1H pyrazole

 2 6.25 g of sodium acetate was added to an acetic acid solution (15 gZ30 ml) of furoyltrifluoroacetone and stirred. To this, 3.65 g of hydrazine hydrate was dripped and held. After dropping, the mixture was heated to 80 ° C. After reaction for 2 hours, heating was stopped and the mixture was allowed to cool. To the reaction mixture was added 250 ml of methylene chloride, and the organic layer was washed with water, saturated aqueous sodium carbonate solution and saturated brine. The extract was dried over sodium sulfate, and the solvent was concentrated to obtain 13.5 g of a crude product.

 [0124] Second step

 1— (2 Black mouth 6 2 Trophe) 1 5 — (Fran 1 2-yl) 3 (Trifluoromethyl) 1H— Pyrazole

0.88 g of the crude product of Step 1 was dissolved in 3 ml of DMF, 0.76 g of 3-chloro-2 fluoro-mouth-trobenzene and l.lg of potassium carbonate were added, and the mixture was heated to 90 ° C. After reacting for 1 hour, the mixture was allowed to cool to room temperature, and the reaction mixture was added to 50 ml of water and extracted with ether. The organic layer was washed with saturated brine and dried over sodium 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 = 1Z0-3Z1) to obtain 0.77 g of the desired product. ¹ ! "I-NMR (300MHz CDC1) δ 8.09 (dd, J = 1.5 and

 Three

 6.9Hz, 1H), 7.85 (dd, J = 1.5 and 6.9Hz, 1H), 7.69 (t, J = 8.3Hz, 1H), 7.34 (dd, J = 0.6 and 1.2Hz, 1H), 6.96 (s, lH), 6.36 (dd, J = 1.5 and 1.8Hz, 1H), 6.13 (dd, J = 0.6 and 2.7Hz, 1H)

[0125] Third step

1- (2 Black mouth 6 Nitrophenol) 3 (Trifluoromethyl) 1H Pyrazole 5 1— (2 Black mouth 6-trofe-nor) 1 5-— (Furan 2- 2-ole) 3 (Trifanololome) 1H Pyrazole 0.76 g and Acetonitrile 5 ml in a mixture of sodium dihydrogen phosphate 1.73 g was cooled and cooled to 0 ° C. A mixed solution of 2.9 g of sodium chlorite and 7 ml of water was gradually added dropwise thereto, and after reacting at room temperature for 19 hours, 3 ml of concentrated hydrochloric acid was added to adjust the pH to 1 or less. The mixed solution was extracted twice with 30 ml of ethyl acetate, and the organic layer was slowly added to a mixed solution of 4 g of sodium disulfite and 50 ml of water at 20 ° C. or lower with stirring. The organic layer was separated, and the aqueous layer was extracted with 30 ml of ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The produced crystal was recrystallized from methylene chloride and hexane to obtain 0.67 g of the desired product. ¹ H-NMR (300MHz CDC1) δ 9.54 (broad s, 1H), 8.11 (d

 Three

 d, J = 1.5 and 6.9Hz, 1H), 7.84 (dd, J = 1.5 and 6.9Hz, 1H), 7.68 (t, J = 8.4Hz, 1H), 7.31 (s, lH)

[0126] Next, typical examples of the compound of the present invention represented by the formula (I) are listed in Table 1. These compounds can be synthesized based on the above synthesis examples or various production methods of the compound of the present invention described above.

 [0127] In Table 1, No. represents the compound number. In Table 1, A1 is -CH- [c-Pr], A2 is -C

 2

 H (Me)-[c-Pr], A3 is -CH- [c-Pr (2-Me)], A4 is -CH- [c-Pr (2,2-CI-1-Me)] The

 2 2 2

 A5 represents -CH- [c-Pr (l-Me)], and A6 represents -CH (Me)-[c-Bu]. In Table 1, M

 2

 e is a methyl group, Et is an ethyl group, Pr is a propyl group, i_Pr is an isopropyl group, c-Pr is a cyclopropyl group, c-Bu is a cyclobutyl group, Ph is a phenyl group, Py Each 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 OPh (4-F) is a phenyl group. The 4-phenyoxy group is substituted with a fluorine atom at the 4-position, and 2-OPy (5-Cl) is a 2-pyridyloxy group substituted with a chlorine atom at the 5-position of the pyridyl group. The description also applies to this.

[0128] [Table 1]

Table 1 (continued)

3] Table 1 (continued)

Four] Table 1 (continued)

Five] Table 1 (continued)

6] Table 1 (continued)

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. Place a damp filter paper on a petri dish with a diameter of 9 cm and air-dry it on it. Placed cabbage leaf pieces. 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 No.l, 10, 12-14, 16-25, 30, 31, 34, 39, 40, 42, 58, 60, 62, 64, 75, 77, 85, 128, 153, 165, 179 185, 186, 188, 190-192, 194, 196-201, 203, 205 and 224 were all determined to have a high insecticidal effect of 90% or more.

 Death rate (%) = (Number of dead insects Z Number of dead insects) X loo

 [0135] Test Example 2 Effect test on silver leaf whitefly

 Leave the first true leaf and let the adult silver-flying moss lay eggs in the pot planted cucumber with the other leaves excised for about 8 hours. Then, leave it in a constant temperature room at 25 ° C for 7-: L0 days, and investigate the number of hatched larvae. Thereafter, the parasitic leaves are immersed for about 10 seconds in a chemical solution prepared so that the concentration of the compound of the present invention is 50 ppm, and then air-dried. 10 to 14 days after treatment After leaving in a constant temperature room at 25 ° C, investigate the number of old larvae and the number of pupae and calculate the control value by the following formula. The compound of the present invention exhibits a high control effect.

 Control value (%) = (l-((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

[0136] Test Example 3 Efficacy Test on Bean Flyfly

 The leaves of green beans that have been uniformly laid with the eggplant sprouts are soaked in a chemical solution prepared so that the concentration of the compound of the present invention is 50 ppm, and air-dried. Place a damp filter paper on a plastic cup 9 cm in diameter and 4 cm in height, and place an air-dried leaf bean leaf on it. Then, close the lid and leave it in a constant temperature room at 25 ° C. After 6 to 8 days of treatment, the number of old larvae and the number of pupae is investigated, and the control value is obtained by the following formula. The compound of the present invention exhibits a high control effect.

Control value (%) = (1 ((Number of old larvae in treated area + number of pupae) Z (Number of old larvae in untreated area + 蛹))) X 100

 [0137] Next, formulation examples are described.

 Formulation Example 1

 (1) Compound of the present invention

 (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) Compound of the present invention

 (2) Talc

 The above is uniformly mixed to form a powder.

[0138] Formulation Example 3

 (1) 20 parts by weight of the compound of the present invention

 (2) N, N-dimethylacetamide 20 parts by weight

 (3) Polyoxyethylene alkylphenol ether 10 layers! I

 (4) Xylene 50 parts by weight

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

 Formulation Example 4

 (1) Clay 68 heavy I

 (2) Sodium sulfonate sulfonate

 (3) Polyoxyethylene alkyl aryl sulfate

 (4) Fine silica 25 parts by weight

 The 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.

 [0139] Formulation Example 5

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

(2) Oxidated polyalkylphenyl phosphate triethanolamine (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.

 [0140] Formulation Example 6

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

 (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 and dilute with an appropriate amount of acetone, and spray onto (4) to remove the acetone to form 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 an ultra low volume formulation.

 [0141] Formulation Example 8

 (1) 40 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) 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-based compound of the present invention has a low dosage and has a very high control effect against pests, and can be used as an agricultural and horticultural pest control agent and animal parasite control agent. The entire contents of the specification, claims, and abstract of Japanese Patent Application 2005-017358 filed on January 25, 2005 are hereby incorporated by reference. It is something that is incorporated.

Claims

The scope of the claims

 Formula (I)

 [Chemical 1]

(Wherein R ¹ is halogen, alkyl, haloalkyl, alkyl, haloalkenyl, alkynyl, haloalkynyl, trialkylsilylethynyl, hydroxy, alkoxy, haloanoloxy, honoreminore, anorequinolenoboninole , Haloanolequinolecanolboninore, force noreboxinole, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cyanide-containing nitro, amine-containing alkylamino, diolalkylamino, optionally substituted phenoxy, Optionally substituted pyridyloxy, optionally substituted, phenoxycarbol or optionally substituted pyridyloxycarbon, R ² is a hydrogen atom, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy , Shi Noarukokishi, alkylsulfonyl O carboxymethyl, a Xia input nitro, Amino, alkylamino or dialkylamino § amino, R ³ is halogen, alkyl, haloalkyl, alkoxy, Bruno, Roarukokishi, Shianoarukokishi, alkylsulfonyl O alkoxy, ShiaIri Nitro, ami-substituted alkylamino or dialkylamino, wherein A is alkyl substituted with Y, Y may be substituted with at least one substituent selected from the group consisting of halogen, alkyl and haloalkyl, C Cycloalkyl, m is 0-4, w is 0-5)

 3-4

 An anthracamide compound or a salt thereof represented.

 [2] Formula (I):

[Chemical 2]

(Wherein R ¹ is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, trialkylsilylethynyl, hydroxy, alkoxy, haloanoloxy, honoreminore, anorequinolecanoleno , Haloanorequinolecanonoboninore, force noreboxinole, alkoxycarbonyl, haloalkoxycarbonyl, aminoamino, alkylaminocarbonyl, dialkylaminocarbonyl, cyano, nitro, amino, alkylamino, dialkylamino, optionally substituted phenoxy, Optionally substituted pyridyloxy, optionally substituted, phenoxycarbol or optionally substituted pyridyloxycarbon, R ² is a hydrogen atom, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy , Cyanoalkoxy, alkylsulfonyloxy, cyano-containing nitro, amino, alkylamino or dialkylamino, R ³ is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyanoalkoxy, alkylsulfonyloxy, cyano-containing Nitro, amino-containing alkylamino or dialkylamino, wherein A is alkyl substituted with Y, Y may be substituted with at least one substituent selected from the group consisting of halogen, alkyl and haloalkyl, C Cycloalkyl, m is 0-4, w is 0-5)

 3-4

A process for producing an anthracamide compound or a salt thereof represented by:

 Equation (1) (Π):

[Chemical 3]

(Wherein RA and m are as defined above) and formula (III):

 (Wherein R, R and w are as defined above, Z is a chlorine atom,

Or a compound represented by

(2) Formula (IV):

[Chemical 5]

(Where

R ² , R ³ , m and w are as defined above) and a compound represented by the formula (V): A-NH (wherein A is as defined above) React or

 2

 Equation (3) (G):

[Chemical 6]

(Wherein R m and w are as defined above, R ^2a is hydrogen, fluorine atom, chlorine atom, bromine atom, alkyl, haloalkyl, alkoxy, haloalkoxy, cyanalkoxy, alkylsulfonyloxy, Nitro, amino, alkylamino or dialkylamino, R ^3a is fluorine atom, chlorine atom, bromine atom, alkyl, haloalkyl, alkoxy, haloalkoxy, cyanoalkoxy, alkylsulfonyloxy, nitro-containing nitro, amino, alkyl Amino or dialkylamino, X is a bromine atom or iodine atom) and a metal cyanide, or

(4) Formula (1-1):

[Chemical 7]

(Where

R ^2a , R ^3a , m, w and X are as described above), a carbon monoxide and a hydrogen donor, or

Equation (5) (G):

[Chemical 8]

(In the formula, R ² , R ³ , m, w and X are as described above, and R ^la is halogen, alkyl, haloalquinole, anorekeninore, haloanorekeninore, anorequininore, noroanorequininore, trianorequinoresinole Ethininore, hydroxy, anorecoxy, haloanorecoxi, anorequinolecanole poninore, haloanorenoreboninore, force norexinore, anorecoxinoreboninore, haloanorecocinoreboninore, aminocarbonyl, alkylaminocarbonyldialkyl Carbonyl, cyano, nitrogen, amino alkylamino, dialkylamino, optionally substituted phenoxy, optionally substituted, pyridyloxy, optionally substituted, phenoxycarbon or optionally substituted V, pyridylo It is a xyball) A compound, or reacting a fluorinating agent,

 (6) Equation (1-1):

[Chemical 9]

(Wherein, RR ^2a , R ^3a , X, m and w are as defined above), and the formula (VI-1):

[Chemical 10]

■ Q (VI-1)

(Wherein Q is alkyl or trialkylsilyl),

Formula (V 2):

[Chemical 11] Shiichi Zn Q (VI-2) (Wherein Q is as defined above, L is a chlorine atom, bromine atom or iodine atom),

Or formula (VI-3):

[Chemical 12]

(VI-3)

(Wherein Q is as defined above, R ^A is alkyl), or any one of the compounds represented by

Equation (1) (1-7):

[Chemical 13]

(In the formula, R ² , R ³ , A, R ^A , m and w are as defined above, and R ^lb is halogen, alkyl, Noanorequinole, Anoleke-nore, Haloanoreke-nore, Anolequino-nore, Haloanoreno-Nore , Hydroxy, anorecoxy, halo anorecoxy, honoreminore, anorequinole decanolole, haloanorequinololebonyl, carboxyl, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, nitro-nitro, amino Including alkylamino, dialkylamino, optionally substituted phenoxy, optionally substituted pyridyloxy, optionally substituted !, phenoxycarbon or optionally substituted, pyridyloxycarbonyl)) With fluorine compound , Equation (1) (1-9):

[Chemical 14]

-9)

(In the formula, R ² , R ³ , A, R ^A , m and w are as defined above, and R ^lc is halogen, alkyl, nitroalkenole, anoreke-nore, haloanoreke-nore, anorequino-re, haloanoleo-nore. , Triolequinolyl silylethynyl, hydroxy, alkoxy, haloalkoxy, formyl, alkylcarbonyl, haloalkylcarbonyl, carboxyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cyano-containing nitro, ami-alkylated alkylamino, dialkylayl-substituted A good phenoxy, an optionally substituted pyridyloxy, an optionally substituted phenoxycarbol or an optionally substituted pyridyloxycarbol) and a base, or

Equation (9) (1-11):

[Chemical 15]

-11)

(Wherein, A, m and w are as defined above, R is fluorine atom, chlorine atom, alkyl, alkyl alkyl, hydroxy, alkoxy, haloalkoxy, formyl, alkylcarbole, haloanorequinolecanevo Ninore, force noreboxinore, anorecoxicanoleboninole, haloanalkoxy force norebonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminoalkylamino, dialkylamino, optionally substituted phenoxy, optionally substituted, Pyridyloxy, may be substituted, phenoxycarbol or may be substituted !, pyridyloxycarbole, and R ^2b is a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, a Noalkoxy, alkylsulfo-loxy, amino An alkylamino or dialkylamino § amino, R ^3b is a fluorine atom, a chlorine atom, alkyl, haloalkyl, alkoxy, haloalkoxy, Shianoarukokishi, Arukirusu sulfo - a Ruokishi Ammi input alkylamino or dialkylamino § amino, R ^B is hydrogen Or a hydrogenated reaction of the compound represented by

(10) Equation (1-1):

[Chemical 16]

(Wherein RR ^2a , R ^3a , A, m, w and X are as defined above), carbon monoxide and R ⁴ — NH (where R ⁴ is a hydrogen atom or alkyl Power to react with

 2

 (11) Formula (1-1):

[Chemical 17]

R ^2a , R ^3a , A, m, w and X are as described above), carbon monoxide, R ⁵ — OH (where R ⁵ is alkyl) and a base Or (12) formula (g 15):

[Chemical 18]

(Wherein, A, m and w are as defined above, R is halogen, alkyl, haloalkyl, anorekeninore, haloanorekeninore, anorequininore, haloanorequininore, trianolenoquinoline-nore, hydroxy, Anolecoxy, haloanorecoxy, honoreminore, anorequinolecanoleponore, nitroalkylcarbonyl, carboxyl, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cyanided alkylamidialkyl Amino-substituted phenoxy, optionally substituted, pyridyloxy, optionally substituted !, phenoxycarbon or optionally substituted pyridyloxycarbon, R ^2e is a hydrogen atom, halogen , Alkyl, haloalkyl , Alkoxy, haloalkoxy, Shianoarukokishi, alkylsulfonyl - Ruokishi a Xia incoming amino input alkylamino or dialkylamino § amino, R represents halogen, alkyl, halo A compound represented by the following formula: alkyl, alkoxy, haloalkoxy, cyanalkoxy, alkylsulfo-loxy, cyanided alkylamino or dialkylamino.

 [3] A pest control agent comprising the anthracamide compound according to claim 1 or a salt thereof as an active ingredient.

 [4] An agricultural and horticultural pest control agent comprising the anthracamide compound or a salt thereof according to claim 1 as an active ingredient.

[5] An insecticide, acaricide or nematicide containing the anthracamide compound or the salt thereof according to claim 1 as an active ingredient.

[6] An animal parasite control agent comprising the anthralamide compound or a salt thereof according to claim 1 as an active ingredient.

[7] An animal ectoparasite-controlling agent comprising the anthra-amide compound or a salt thereof according to claim 1 as an active ingredient.

[8] A prophylactic or therapeutic agent for parasite-derived animal diseases comprising the anthra-amide compound or the salt thereof according to claim 1 as an active ingredient

[9] A method for controlling pests by applying an effective amount of the anthranilamide compound or the salt thereof according to claim 1.