JP2008024697A - Pest control agent comprising new pyridyl-methanamine derivative or salt thereof - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new pest control agent having ultrahigh control effects on pests with a small dose. <P>SOLUTION: The pest control agent comprises a pyridyl-methanamine derivative or a salt thereof as an active ingredient. The pyridyl-methanamine derivative is represented by formula of figure (wherein, R<SP>1</SP>is a hydrogen atom, an alkyl, a heterocyclic group or the like; R<SP>2</SP>and R<SP>3</SP>are each independently a hydrogen atom, a halogen, a cyano, a heterocyclic group or the like; R<SP>4</SP>is a trifluoromethyl or a chlorodifluoromethyl; R<SP>5</SP>is a hydrogen atom, a halogen, a cyano, a nitro, an alkyl or the like; R<SP>6</SP>and R<SP>7</SP>are each independently a hydrogen atom, a cyano, an alkyl, a haloalkyl or the like; R<SP>8</SP>is an alkyl, a cycloalkyl, a halogen, a haloalkyl, a cyano, a nitro or the like; and n is an integer of 0-4). <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a novel pyridyl-methanamine derivative or a salt thereof, and a pest control agent containing the same as an active ingredient.

Patent Documents 1 to 3 disclose pyridine derivatives each having a certain chemical structure. However, the compound described in Patent Document 1 and the compound described in Patent Document 2 are different from the pyridyl-methanamine derivative of the present invention in the R ⁴ part and R ⁵ part in the following formula (I), respectively. Patent Document 3 does not specifically disclose the pyridyl-methanamine derivative of the present invention. Furthermore, all the compounds described in Patent Documents 1 to 3 are compounds for pharmaceutical use, not compounds for pest control use.
Non-Patent Document 1 discloses N- (2-pyridylmethyl) -3,5,6-trichloro-4- (trifluoromethyl) -2-pyridylamine, which is a compound included in the formula (I) described later. Although described, a pest control agent containing this compound as an active ingredient is not described.

International Publication No. WO01 / 62233 International Publication WO02 / 66470 International Publication No. WO04 / 91518 Chemistry Express, 7,473-476 (1992)

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

  The present inventors have made various studies on pyridyl-methanamine derivatives in order to find better pest control agents. As a result, it was found that the novel pyridyl-methanamine derivative has an extremely high control effect against pests at a low dosage, and also has safety against crops, pest natural enemies or mammals. Completed the invention.

  That is, the present invention relates to the formula (I):

[Wherein, R ¹ is a hydrogen atom, alkyl ^optionally substituted with R ^b , alkenyl optionally substituted with R ^b , alkynyl optionally substituted with R ^b , aryl, cyano, N═CHR ^c , OR ^c , S (O) _p R ^c , COSR ^c , COOR ^c or COR ^c , or R ¹ is a heterocyclic group optionally substituted with alkyl or haloalkyl; R ² and R ³ are each independently Hydrogen atom, halogen, cyano, nitro, alkyl optionally substituted with R ⁸ , cycloalkyl, alkenyl, alkynyl, aryl, heterocyclic group, NR ^a R ^c , OR ^a , SR ^a , COR ^a , COOR ^a , CONR ^a R ^c , CH═NOR ^a , SO ₂ R ^a or SOR ^a ; R ⁴ is trifluoromethyl or chlorodifluoromethyl; R ⁵ is substituted with a hydrogen atom, halogen, cyano, nitro, R ⁸ Moyo Alkyl, alkenyl which may be substituted by R ^8, which may be substituted by R ^{8 alkynyl, OR a, SR a, NR} a R c, be a COOR ^a or COR ^a; R ⁶ and R ⁷ are each independently , A hydrogen atom, cyano, alkyl, haloalkyl or cycloalkyl, or R ⁶ and R ⁷ together may form a cycloalkyl having 3 to 6 carbon atoms which may be substituted with halogen; R ⁸ Is alkyl, cycloalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, halogen, haloalkyl, cyano, nitro, aryl optionally substituted with halogen, heterocyclic group optionally substituted with halogen, halogen substituted Good heterocyclic oxy, CONR ^a R ^c , COR ^c , COOR ^c , NR ^a R ^c or OR ^a ; R ^a is a hydrogen atom, alkyl, Black alkyl, haloalkyl or a heterocyclic alkyl; R ^b is halogen, may be substituted by R ⁸ aryl, which may be substituted by R ⁸ heterocyclic group, which may be substituted by R ⁸ heterocyclyloxy, Heterocyclic thio, cyano, NR ^a R ^c , NHCOOR ^a , COR ^c , COOR ^c , CONR ^a R ^c , alkoxyalkoxy, OR ^a or S (O) _p R ^a optionally substituted by R ⁸ ; R ^c is a hydrogen atom, alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, hydroxyalkyl, aryl optionally substituted with halogen or heterocyclic group optionally substituted with haloalkyl; n is an integer of 0-4; p is an integer of 0 to 2, and the NR ^a R ^c moiety in each substituent described above is a 5- or 6-membered heterocyclic ring together with the nitrogen atom to which R ^a and R ^c are bonded together. Shape Pyridyl represented by may also] be - methanamine derivative or its salt, as well as pesticide them as an active ingredient.

  The pest control agent containing the pyridyl-methanamine derivative represented by the formula (I) as an active ingredient has a very high control effect against pests at a low dose.

Examples of the halogen in the formula (I) or the halogen as a substituent include fluorine, chlorine, bromine and iodine atoms. The number of halogens as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen may be the same or different. Further, the halogen substitution position may be any position.
The alkyl in formula (I) or the alkyl moiety in alkoxy may be linear or branched, and specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, Examples thereof include those of C _1-6 such as hexyl.
Examples of cycloalkyl in formula (I) include C _3-6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The alkenyl in the formula (I) may be linear or branched, and specific examples thereof include vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3-butadienyl, 1 - like those of _{C 2-6,} such as hexenyl.
The alkynyl in the formula (I) may be linear or branched, and specific examples thereof include ethynyl, 2-butynyl, 2-pentynyl, 3-methyl-1-butynyl, 2-pentene- Examples include C _2-6 such as 4-ynyl and 3-hexynyl.
Examples of the aryl in the formula (I) include C _6-10 aryl such as phenyl and naphthyl.

  The heterocyclic group moiety in the heterocyclic group, heterocyclic alkyl, heterocyclic oxy or heterocyclic thio in the formula (I) includes a condensed heterocyclic group in addition to a monocyclic heterocyclic group. Examples of monocyclic heterocyclic groups include 3-membered heterocyclic groups such as oxiranyl; furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl, oxazolyl, isoxazolyl, dihydroisoxazolyl, thiazolyl, isothiazolyl, imidazolyl 5-membered heterocyclic groups such as imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, 1,3-dioxolanyl, 1,3-oxathiolanyl, 1,3-oxathiolanyl-3-oxide; Pyridyl, piperidinyl, dioxanyl, oxazinyl, morpholinyl, thiazinyl, pyridazinyl, pyrimidinyl, pyrazinyl, piperazinyl, triazinyl, 1,3-dioxanyl, teto Hidoropiraniru, 2H-1,4 Okisachiiniru include 6-membered heterocyclic group such as 1,3-dithiolanyl. Among these monocyclic heterocyclic groups, a 5- or 6-membered heterocyclic group containing 1 to 4 of at least one atom selected from the group consisting of O, S and N is desirable. Examples of the condensed heterocyclic group include benzofuranyl, isobenzofuranyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, benzothienyl, isobenzothienyl, dihydrobenzothienyl, dihydroisobenzothienyl, tetrahydrobenzothienyl, indolyl, isoindolyl, Benzoxazolyl, benzothiazolyl, indazolyl, benzimidazolyl, benzodioxolanyl, benzodioxanyl, chromenyl, chromanyl, isochromanyl, chromonyl, chromanonyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizylyl , Naphthyridinyl, pteridinyl, dihydrobenzoxazinyl, dihydrobenzoxazolinonyl, dihydride Benzoxadiazoles nonyl, benzothiadiazole oxa sulfonyl, etc. imidazopyridinyl and the like. Among these condensed heterocyclic groups, an 8 to 10-membered condensed heterocyclic group containing 1 to 4 of at least one atom selected from the group consisting of O, S and N is desirable.

The NR ^a R ^c moiety contained in each substituent in formula (I) may be formed by combining R ^a and R ^c together with the nitrogen atom to which they are bonded to form a 5- or 6-membered heterocyclic ring. Good. The 5-membered or 6-membered heterocyclic ring may further include one or more heteroatoms in addition to the nitrogen atom to which R ^a and R ^c are bonded. Such heterocycles include pyrrolidinyl, pyrazolidinyl, piperazinyl, morpholinyl and the like. Examples of the cycloalkyl having 3 to 6 carbon atoms formed by R ⁶ and R ⁷ in the formula (I) together include cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. It may be substituted with an atom.

  The salt of the pyridyl-methanamine derivative represented by the formula (I) includes any agriculturally acceptable salt, for example, alkali metal salts such as sodium salt and potassium salt; magnesium salt Alkaline earth metal salts such as calcium salts; ammonium salts such as dimethylammonium salts and triethylammonium salts; inorganic acid salts such as hydrochlorides, perchlorates, sulfates and nitrates; acetates and methanesulfonic acid Examples thereof include organic acid salts such as salts.

  In the pyridyl-methanamine derivative represented by the formula (I), there may be an isomer such as an optical isomer or a geometric isomer. In the present invention, both of the isomers and isomer mixtures are present. included. In the present specification, unless otherwise specified, isomers are described as a mixture. The present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field. Depending on the type of isomer, there may be a chemical structure different from that of the formula (I). However, since those skilled in the art can fully recognize that they are related to isomers, the scope of the present invention. It is clear that it is within.

The pyridyl-methanamine derivative represented by the formula (I) or a salt thereof can be produced according to the following production methods [1] to [10] and a usual salt production method.
Manufacturing method [1]

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and n are as described above; X is a halogen, and the halogen is fluorine, chlorine, bromine or iodine. Atom.
The reaction of the production method [1] can be performed in the presence of a solvent.
Any solvent may be used as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane and heptane Aliphatic ethers such as petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as methyl acetate and ethyl acetate; acetonitrile and propionitrile Nitriles such as; acid amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; phosphoric acid amides such as hexamethylphosphoramide; chloroform Dichloromethane, carbon tetrachloride, halogenated hydrocarbons such as 1,2-dichloroethane; can mixtures of these solvents.

  In the reaction of the production method [1], the reaction can be carried out in the presence of a base as necessary in order to carry out the reaction efficiently. Examples of the base include organic bases such as triethylamine and pyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate; lithium hydrogen carbonate and carbonate Alkali metal hydrogen carbonates such as sodium hydride and potassium hydrogen carbonate; Alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride; Alkalis such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide And metal alkoxides.

In the reaction of the production method [1], the compound of the formula (III) is used in a ratio of 0.8 to 5 equivalents, preferably 1 to 2.5 equivalents per 1 mol of the compound of the formula (II). it can.
The reaction of the production method [1] is usually performed at a reaction temperature of 0 to 150 ° C, preferably 0 to 100 ° C. The reaction time is usually 0.5 to 100 hours.

Reaction conditions in the production method [1] can be combined with each other as appropriate. Further, some of these reaction conditions have a normal range of reaction conditions and a desired range of reaction conditions, and these can also be appropriately selected and combined with each other.
Manufacturing method [2]

R ^1a is optionally substituted by R ^b alkyl, alkenyl which may be substituted with R ^b, which may be substituted by R ^b alkynyl, aryl which may be substituted by alkyl or haloalkyl heterocyclic group, N = CHR ^c , OR ^c , S (O) _p R ^c , COSR ^c , COOR ^c or COR ^c , R ^b, R ^c , p, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , n and X are as described above.
The reaction of the production process [2] can be carried out in the presence of a base and a solvent.
Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide Alkali metal alkoxides such as sodium ethoxide, potassium tertiary butoxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; triethylamine; And organic bases such as pyridine. The base can be used in an amount of 1 to 3 equivalents, preferably 1 to 1.5 equivalents, relative to the compound of formula (V-1).

  Any solvent may be used as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane and heptane Aliphatic ethers such as petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as methyl acetate and ethyl acetate; acetonitrile and propionitrile Nitriles such as; acid amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; phosphoric acid amides such as hexamethylphosphoramide; chloroform Dichloromethane, carbon tetrachloride, halogenated hydrocarbons such as 1,2-dichloroethane; can mixtures of these solvents.

In the reaction of the production method [2], the compound of the formula (VI) can be used at a ratio of 0.8 to 2 equivalents with respect to 1 mol of the compound of the formula (V-1).
The reaction of the production process [2] is usually performed at a reaction temperature of 0 to 100 ° C, preferably 0 to 50 ° C. The reaction time is usually 0.5 to 24 hours, preferably 0.5 to 5 hours.

The reaction conditions in the production method [2] can be combined with each other as appropriate. Further, some of these reaction conditions have a normal range of reaction conditions and a desired range of reaction conditions, and these can also be appropriately selected and combined with each other.
Manufacturing method [3]

R ^1a , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , n and X are as described above.
The reaction of the production method [3] can be performed in the presence of a base and a solvent.
Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide Alkali metal alkoxides such as sodium ethoxide, potassium tertiary butoxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; triethylamine; And organic bases such as pyridine. The base can be used in an amount of 1 to 3 equivalents, preferably 1 to 1.5 equivalents, relative to the compound of formula (I-1).

  Any solvent may be used as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane and heptane Aliphatic ethers such as petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as methyl acetate and ethyl acetate; acetonitrile and propionitrile Nitriles such as; acid amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; phosphoric acid amides such as hexamethylphosphoramide; chloroform Dichloromethane, carbon tetrachloride, halogenated hydrocarbons such as 1,2-dichloroethane; can mixtures of these solvents.

In the reaction of the production method [3], the compound of the formula (VII) can be used at a ratio of 0.8 to 2 equivalents per 1 mol of the compound of the formula (I-1).
The reaction of the production method [3] is usually performed at a reaction temperature of 0 to 100 ° C, preferably 0 to 50 ° C. The reaction time is usually 0.5 to 24 hours, preferably 0.5 to 5 hours.

Reaction conditions in the production method [3] can be combined with each other as appropriate. Further, some of these reaction conditions have a normal range of reaction conditions and a desired range of reaction conditions, and these can also be appropriately selected and combined with each other.
Manufacturing method [4]

R ^1a , R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , n and X are as described above.
The halogenation reaction of the production method [4] can be performed using a halogenating agent in the presence of a solvent.
Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, and the like. The halogenating agent is used in an amount of 1 to 2 equivalents, preferably 1 to 1.5 equivalents, relative to 1 mol of each compound of formula (V-2), formula (I-3) and formula (I-4). it can.

The solvent may be any solvent inert to the reaction, for example, acid amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile, propionitrile, and acrylonitrile; chloroform, dichloromethane, tetrachloride Halogenated hydrocarbons such as carbon and 1,2-dichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene; esters such as methyl acetate and ethyl acetate; organic acids such as acetic acid; Can be mentioned.
The halogenation reaction is usually carried out at a reaction temperature of 0 to 150 ° C., preferably 20 to 100 ° C. The reaction time is usually 0.5 to 24 hours, preferably 0.5 to 12 hours.

The reaction of the compound of formula (V-3) in the production method [4] and the compound of formula (VI) can be carried out in the same manner as in the production method [2].
The reaction of the compound of formula (I-5) in the production method [4] and the compound of formula (VII) can be carried out in the same manner as in the production method [3].
Manufacturing method [5]

R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , n and X are as described above, and R ^2a is alkyl, cycloalkyl, alkenyl, alkynyl optionally substituted with R ^8. , Aryl or a heterocyclic group, and M is a leaving group that generates R ^2a such as copper, boron, zinc, magnesium, lithium, tin, and silicon.

The reaction for the production process [5] can be carried out using a compound represented by the formula ^{MR 2a} in the presence of a base.
Examples of the compound represented by the formula M-R ^2a include organic copper compounds, organic boron compounds, organic zinc compounds, organic magnesium compounds, organic lithium compounds, organic tin compounds, and organic silicon compounds. The compound can be used in an amount of 1 to 3 equivalents, preferably 1 to 1.5 equivalents, per 1 mol of the compound of formula (I-7).
Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; sodium methoxide, sodium ethoxide and potassium tertiary. Alkali metal alkoxides such as butoxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; organic bases such as triethylamine and pyridine; be able to.

  In the reaction of the production method [5], a catalyst such as a palladium compound or a nickel compound can be used as necessary in order to carry out the reaction efficiently.

  The reaction of the production process [5] can be carried out in the presence of a solvent, if necessary. The solvent may be any solvent as long as it is inert to the reaction, for example, alcohols such as methanol, ethanol, propanol and butanol; ketones such as acetone, methyl ethyl ketone, dimethyl ketone, diethyl ketone and methyl isobutyl ketone; Aromatic hydrocarbons such as benzene, toluene and xylene; Aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane Esters such as methyl acetate and ethyl acetate; Nitriles such as acetonitrile and propionitrile; Acid amides such as dimethylformamide and dimethylacetamide; Sulfur such as dimethyl sulfoxide Sulfones such as sulfolane; Phosphoric amides such as hexamethylphosphoramide; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; Water; be able to.

The reaction of the production process [5] is usually carried out at a reaction temperature of 0 to 200 ° C, preferably 20 to 120 ° C. The reaction time is usually 0.5 to 24 hours.
The reaction conditions in the production method [5] can be combined with each other as appropriate. Further, some of these reaction conditions have a normal range of reaction conditions and a desired range of reaction conditions, and these can also be appropriately selected and combined with each other.
Manufacturing method [6]

R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , n and X are as described above, and R ^2b is NR ^a R ^c , OR ^a or SR ^a .
The nucleophilic substitution reaction in the production method [6] can be performed using a nucleophilic reagent in the presence of a solvent.
Examples of nucleophiles include alkali metal alkoxides such as sodium methoxide and sodium ethoxide; alkali metal mercaptides such as sodium methyl mercaptan; primary and secondary amines such as methylamine, dimethylamine and piperidine; Can be mentioned. The nucleophile can be used in an amount of 1 to 5 equivalents, preferably 1 to 3 equivalents, per 1 mol of the compound of formula (I-7).

  The solvent may be any solvent as long as it is inert to the reaction, for example, alcohols such as methanol, ethanol, propanol and butanol; ketones such as acetone, methyl ethyl ketone, dimethyl ketone, diethyl ketone and methyl isobutyl ketone; Aromatic hydrocarbons such as benzene, toluene and xylene; Aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane Esters such as methyl acetate and ethyl acetate; Nitriles such as acetonitrile and propionitrile; Acid amides such as dimethylformamide and dimethylacetamide; Sulfur such as dimethyl sulfoxide Sulfones such as sulfolane; Phosphoric amides such as hexamethylphosphoramide; Halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; Water; be able to.

The nucleophilic substitution reaction in the production process [6] is usually performed at a reaction temperature of 0 to 200 ° C, preferably 0 to 100 ° C. The reaction time is usually 0.5 to 24 hours.
Reaction conditions in the production method [6] can be combined with each other as appropriate. Further, some of these reaction conditions have a normal range of reaction conditions and a desired range of reaction conditions, and these can also be appropriately selected and combined with each other.
Manufacturing method [7]

A and A ′ are each independently a hydrogen atom, cyano, alkyl, haloalkyl, cycloalkyl, aryl or a heterocyclic group optionally substituted with R ⁸ , and A ″ is alkyl, alkenyl, haloalkyl, cycloalkyl or cyano. And M ^a is ^a leaving group that generates magnesium halide, metal, or CN ⁻ , and R ² , R ³ , R ⁴ , R ^5, and R ⁸ are as described above.

The compound of formula (IX) can be produced by subjecting a compound of formula (V-4) and a compound of formula (VIII) to a condensation reaction in a solvent.
The solvent may be any solvent as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane, Aliphatic hydrocarbons such as heptane, petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as ethyl acetate and methyl acetate; dimethylformamide and dimethylacetamide Acid amides such as; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane; Phosphoric amides such as hexamethylphosphoramide; Chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane Halogenated hydrocarbons such as; can mixtures of these solvents.

In order to efficiently perform the condensation reaction, an acid catalyst can be used as necessary. Examples of the acid catalyst include inorganic acids such as hydrochloric acid and sulfuric acid; organic acids such as acetic acid, camphorsulfonic acid, p-toluenesulfonic acid, and pyridinium p-toluenesulfonate;
In the condensation reaction, the compound of the formula (VIII) can be used in an amount of 1 to 2 equivalents, preferably 1.2 to 1.5 equivalents, relative to 1 mol of the compound of the formula (V-4).
The condensation reaction is usually performed at a reaction temperature of 0 to 150 ° C, preferably 50 to 100 ° C. The reaction time is usually 5 to 100 hours.

  The condensation reaction conditions can be combined with each other as appropriate. Further, some of these reaction conditions have a normal range of reaction conditions and a desired range of reaction conditions, and these can also be appropriately selected and combined with each other.

The compound of formula (X) can be produced by reacting the compound of formula (IX) with a reducing agent in a solvent.
Examples of the reducing agent include metal hydrides such as lithium aluminum hydride, sodium borohydride and sodium cyanoborohydride; hydrosilanes such as triethylsilane and trichlorosilane. Further, catalytic reduction, a method using ammonium formate as a reducing agent in the Leuckart-Wallach reaction, and the like can also be selected.

  The solvent may be any solvent as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane, Aliphatic hydrocarbons such as heptane, petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; acid amides such as dimethylformamide and dimethylacetamide; dimethyl sulfoxide and the like Sulfoxides; sulfones such as sulfolane; phosphoric acid amides such as hexamethylphosphoramide; esters such as ethyl acetate and methyl acetate; chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane Halogenated hydrocarbons such as; can mixtures of these solvents.

The reduction reaction is usually performed at a reaction temperature of 0 to 100 ° C, desirably 0 to 40 ° C. The reaction time is usually 1 to 40 hours.
The reduction reaction conditions can be combined with each other as appropriate. Further, some of these reaction conditions have a normal range of reaction conditions and a desired range of reaction conditions, and these can also be appropriately selected and combined with each other.

The compound of the formula (XII) can be produced by reacting the compound of the formula (IX) and the compound of the formula (XI) in a solvent and then hydrolyzing it by a usual method.
The compound of formula (XI) is an alkylmagnesium halide such as methylmagnesium bromide or isopropylmagnesium chloride, an alkenylmagnesium halide such as allylmagnesium bromide, trifluoromethyl when A ″ is alkyl, alkenyl, haloalkyl or cycloalkyl. Grignard reagents such as haloalkylmagnesium halides such as magnesium bromide and cycloalkylmagnesium halides such as cyclopropylmagnesium bromide; alkyllithiums such as methyllithium and butyllithium; alkylzinc or dialkyl such as methylzinc, ethylzinc and diethylzinc In addition, when A ″ is cyano, hydrogen cyanide, trimethylsilyl cyanide, cyanide Cyanide compounds such as Ribuchirusuzu can be mentioned. The compound of the formula (XI) can be used in an amount of usually 1 to 4 equivalents, preferably 1.2 to 1.5 equivalents, per 1 mol of the compound of the formula (IX).

  The solvent may be any solvent as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane, Aliphatic hydrocarbons such as heptane, petroleum ether, ligroin, petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane; phosphoric acid amides such as hexamethylphosphoramide; chloroform, dichloromethane , Halogenated hydrocarbons such as carbon tetrachloride and 1,2-dichloroethane; and mixed solvents thereof.

This reaction is usually carried out at a reaction temperature of 0 to 100 ° C, preferably 0 to 40 ° C. The reaction time is usually 1 to 50 hours.
Manufacturing method [8]

R ¹ , R ² , R ³ , R ⁴ , R ⁵ and X are as described above.
The reaction of the production process [8] can be carried out in the presence of a solvent.
Examples of the solvent include alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin and petroleum benzine; Ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as methyl acetate and ethyl acetate; nitriles such as acetonitrile and propionitrile; acid amides such as dimethylformamide and dimethylacetamide; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane; Phosphoric amides such as hexamethylphosphoramide; Chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane Halogenated hydrocarbons; can mixtures of these solvents.

  In the reaction of the production process [8], the reaction can be carried out in the presence of a base as necessary in order to carry out the reaction efficiently. Examples of the base include organic bases such as triethylamine and pyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate and potassium carbonate; lithium hydrogen carbonate and carbonate Alkali metal hydrogen carbonates such as sodium hydride and potassium hydrogen carbonate; Alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride; Alkalis such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide And metal alkoxides.

In the reaction of the production method [8], the compound of the formula (IV) is used in a ratio of 0.8 to 5 equivalents, preferably 1 to 2.5 equivalents per 1 mol of the compound of the formula (II). it can.
The reaction of the production process [8] is usually performed at a reaction temperature of 0 to 150 ° C, preferably 0 to 100 ° C. The reaction time is usually 0.5 to 100 hours.
Reaction conditions in the production method [8] can be combined with each other as appropriate. Further, some of these reaction conditions have a normal range of reaction conditions and a desired range of reaction conditions, and these can also be appropriately selected and combined with each other.
Manufacturing method [9]

R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , n and X are as described above.
The reaction of the production process [9] can be carried out in the presence of a base and a solvent.
Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide Alkali metal alkoxides such as sodium ethoxide, potassium tertiary butoxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; triethylamine; And organic bases such as pyridine. The base can be used in an amount of 1 to 3 equivalents per mole of the compound of formula (V-4). In order to obtain a compound of formula (I-1), it is desirable to use 1 to 1.5 equivalents of a base, and in order to obtain a compound of formula (XIII), 2 to 2.5 equivalents of a base are used. Is desirable.

  Any solvent may be used as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane and heptane Aliphatic ethers such as petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as methyl acetate and ethyl acetate; acetonitrile and propionitrile Nitriles such as; acid amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; phosphoric acid amides such as hexamethylphosphoramide; chloroform Dichloromethane, carbon tetrachloride, halogenated hydrocarbons such as 1,2-dichloroethane; can mixtures of these solvents.

In the reaction of the production method [9], the compound of the formula (VI) can be used at a ratio of 0.8 to 2.5 equivalents relative to 1 mol of the compound of the formula (V-4). In order to obtain the compound of the formula (I-1), it is desirable to use 0.8 to 1.5 equivalents of the compound of the formula (VI), and in order to obtain the compound of the formula (XIII) It is desirable to use 2 to 2.5 equivalents of the compound of
The reaction of the production process [9] is usually carried out at a reaction temperature of 0 to 100 ° C, preferably 0 to 50 ° C. The reaction time is usually 0.5 to 24 hours.

Reaction conditions in the production method [9] can be combined with each other as appropriate. Further, some of these reaction conditions have a normal range of reaction conditions and a desired range of reaction conditions, and these can also be appropriately selected and combined with each other.
Manufacturing method [10]

R ² , R ⁴ , R ⁵ and X are as described above.
The reaction of the production process [10] can be carried out using a cyanating agent in the presence of a solvent.
Examples of the cyanating agent include copper cyanide, zinc cyanide, sodium cyanide, trimethylsilyl cyanide, tributyltin cyanide, etc., but copper cyanide is preferable.

  Examples of the solvent include alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin and petroleum benzine; Ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as methyl acetate and ethyl acetate; nitriles such as acetonitrile and propionitrile; acid amides such as dimethylformamide and dimethylacetamide; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane; Phosphate amides such as hexamethylphosphoramide; Chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane Halogenated hydrocarbons; can mixtures of these solvents.

In the reaction of the production method [10], the cyanating agent may be used in a proportion of 0.8 to 5 equivalents, preferably 1 to 2.5 equivalents, relative to 1 mol of the compound of the formula (V-3). it can.
The reaction of the production process [10] is usually performed at a reaction temperature of 80 to 200 ° C, preferably 100 to 150 ° C. The reaction time is usually 1 to 24 hours.
Reaction conditions in the production method [10] can be combined with each other as appropriate. Further, some of these reaction conditions have a normal range of reaction conditions and a desired range of reaction conditions, and these can also be appropriately selected and combined with each other.

  Hereinafter, desirable embodiments of the pest control agent containing the compound of the present invention (hereinafter, meaning all compounds represented by the formula (I) unless otherwise specified) will be described. The pest control agent containing the compound of the present invention includes, for example, various pest control agents that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural pest control agents, and pest control agents that parasitize animals, that is, animal parasitics. It is particularly useful as a biocontrol agent.

  Pesticides for agricultural and horticultural use are useful as, for example, insecticides, acaricides, nematicides, and soil-killing insecticides. Specifically, urticae, spider mites, kanzawa spider mites, citrus spider mites, apple spider mites, citrus dust mites, mandarin oranges Plant parasitic mites such as rust mites and mites; aphids such as peach aphids and cotton aphids; diamondback moths, weevil, scallops, codling moths, ball worms, tobacco worms, mai moths, yellow moths, prickly pears, Colorado Agricultural pests such as leaf beetle, cucumber beetle, ball weevil, leafhoppers, leafhoppers, scale insects, stink bugs, whitefly, thrips, grasshoppers, fly flies, scarab beetles, tamanayaga, kaburagaga, ants, etc .; , Plant parasitic nematodes such as cyst nematodes, nematode nematodes, rice scented nematodes, strawberry nematodes, pine wood nematodes, etc .; gastropods such as slugs, maimai, etc .; Pests such as mosquitoes; hygiene pests such as house dust mites, cockroaches, house flies, and mosquitoes; storage pests such as bark moths, azuki beetles, bark beetles, bark beetles, bark beetles, etc .; It is effective for controlling indoor pests such as clothing, house pests, indoor dust mites, such as Scarlet mite, Scarlet mite, Southern mite. Among them, the agricultural and horticultural pest control agent containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. Moreover, the agricultural and horticultural pesticide containing the compound of the present invention is also effective for controlling various resistant pests against drugs such as organic phosphorus agents, carbamate agents, and synthetic pyrethroid agents. Furthermore, since the compound of the present invention has excellent osmotic transfer properties, soil harmful insects, mites, nematodes by treating agricultural and horticultural pesticides containing the compound of the present invention on the soil It is possible to control pests on the foliage at the same time as the control of gastropods and isopods.

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

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

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

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

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

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

  In the above-mentioned other pesticides, the active ingredient compounds (generic name; including those currently in application) of insecticides, acaricides, nematicides or soil pesticides include, for example, profenofos, dichlorvos ), Fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos-methyl, acephate, prothiofos, fosthiazate, phosphocarb, usa ), Disulfoton, chlorpyrifos, demeton-S-methyl, dimethoate, metamidophos, imicyafos, isoxathion, isofenphos, isofenphos, Etion, etrimphos (e trimfos, quinalphos, dimethylvinphos, sulprofos, thiometon, vamidothion, pyraclofos, pyridaphenthion, pyrimiphos-methyl, propaphos ), Posalone, formothion, malathion, tetrachlovinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion, phentoate ( phenthoate, ESP, azinphos-methyl, fenthion, heptenophos, methoxychlor, parathion, monocrotophos, parathion-methyl, terbufos ), Phosphamide (Phospamidon), phosmet (phosmet), organic phosphoric acid ester compounds such as folate (phorate);

Carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, fenobucarb Carbamates such as carbosulfan, benfuracarb, bendiocarb, furathiocab, isoprocarb, metolcarb, xylylcarb, XMC, fenothiocarb Compound;
Nereistoxin derivatives such as cartap, thiocyclam, bensultap, sodium thiosultap-sodium;
Organochlorine compounds such as dicophor, tetradifon, endosulfan, dienochlor, dieldrin;
Organometallic compounds such as fenbutatin oxide and cyhexatin;

Fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, etofenprox, fenpropathrin, bifenthrin (bifenthrin) , Cyfluthrin, flucythrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrin, esfenvalerate, tetramethrin ( tetramethrin, resmethrin, protrifenbute, zeta-cypermethrin, acrinathrin, alpha-cypermethrin, allethrin, ga Masihalothrin (gamma-cyhalothrin), theta-cypermethrin (theta-cypermethrin), tau-fluvalinate, tralomethrin, profluthrin, beta-cypermethrin, beta-cyfluthrin (beta-) pyrethroid compounds such as cyfluthrin), mettofluthrin;
Diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, flufluuron, flufluuron ), Bistrifluron, benzoylurea compounds such as fluazuron;
Juvenile hormone-like compounds such as metoprene, pyriproxyfen, fenoxycarb, diofenolan;
Pyridazinone compounds such as pyridaben;

Pyrazole compounds such as fenpyroximate, fipronil, tebufenpyrad, ethiprole, tolfenpyrad, acetoprole, pyrafluprole, pyriprole;
Neonicochioids such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, dinotefuran, nithiazine;
Hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, halofenozide;

  Other compounds include flonicamid, buprofezin, hexythiazox, amitraz, chlordimeform, silafluofen, triazamate, pymetrozine, rimidi Chlorfenapyr, indoxacarb, acequinocyl, etoxazole, cyromazine, 1,3-dichloropropene, diafenthiuron, benclothiaz (Benclothiaz), flufenerim, pyridalyl, spirodiclofen, bifenazate, spiromesifen, spirotetramat Propargite, clofentezine, fluacrypyrim, metaflumizone, flubendiamide, chlorantraniliprole, cyflumetofen, cyenofluazone, pyenofluafen Compounds like fenazaquin, pyridaben, amidoflumet, chlorobenzoate, sulfluramid, hydramethylnon, metaldehyde, ryanodine Can be mentioned.

  Furthermore, Bacillus thuringienses aizawai, Bacillus thuringienses kurstaki, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses tenebrionis or crystalline protein toxins produced by Bacillus thuringienses, entomopathogenic fungi, nematode pathogenic fungi, etc. Microbial pesticides such as: avermectin, emamectin-benzooate, milbemectin, spinosad, ivermectin, lepimectin, spinetoram, abamectin, abamectin Antibiotics such as (emamectin) or semi-synthetic substances thereof; natural products such as Azadirachtin and Rotenone; repellents such as deet.

In the above-mentioned other agricultural chemicals, the bactericidal active ingredient compounds (generic name; including those for which application has been filed, or Japan Plant Protection Association test code) include, for example, mepanipyrim, pyrimethanil, cyprodinil ( anilinopyrimidine compounds such as cyprodinil);
Pyridinamine compounds such as fluazinam;
Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, o Oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol, flutriafol, difenoconazole ), Fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, probenazole, cimeconazole, pefurazoate, ipconazole ipconazole), azole compounds such as imibenconazole;

Quinoxaline compounds such as quinomethionate;
Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, thiram;
Organochlorine compounds such as fthalide, chlorothalonil, quintozene;
Imidazole compounds such as benomyl, thiophanate-Methyl, carbendazim, thiabendazole, fuberiazole, cyazofamid;
Cyanoacetamide compounds such as cymoxanil;
Metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, offurace, benalaxyl, benalaxyl-M, also known as kiralaxyl, chiax ), Phenylamide compounds such as furalaxyl, cyprofuram;

Sulfenic acid compounds such as dichlofluanid;
Copper-based compounds such as cupric hydroxide and oxine copper;
Isoxazole compounds such as hymexazol;
Fosetyl aluminum (fosetyl-Al), Turkish phosmethyl (tolcofos-methyl), S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate, edifenphos, Organophosphorus compounds such as iprobenfos;
N-halogenothioalkyl compounds such as captan, captafol, folpet;
Dicarboximide compounds such as procymidone, iprodione, vinclozolin;

Benzanilide compounds such as flutolanil, mepronil, zoxamid, tiadinil;
Anilide compounds such as carboxin, oxycarboxin, thifluzamide, penthiopyrad, boscalid;
Piperazine compounds such as triforine;
Pyridine compounds such as pyrifenox;
Carbinol compounds such as fenarimol, flutriafol;
Piperidine compounds such as fenpropidine;
Morpholine compounds such as fenpropimorph and tridemorph;

Organotin compounds such as fentin hydroxide and fentin acetate;
Urea-based compounds such as pencycuron;
Synamic acid compounds such as dimethomorph, flumorph;
Phenyl carbamate compounds such as dietofencarb;
Cyanopyrrole compounds such as fludioxonil and fenpiclonil;
Azoxystrobin, kresoxim-Methyl, metminomino, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin Strobilurin-based compounds such as pyraclostrobin, fluoxastrobin, fluacrypyrin;

Oxazolidinone compounds such as famoxadone;
Thiazole carboxamide compounds such as ethaboxam;
Silylamide compounds such as silthiopham;
Amino acid amide carbamate compounds such as iprovalicarb, benchthiavalicarb-isopropyl;
Imidazolidine compounds such as fenamidone;
Hydroxyanilide compounds such as fenhexamid;
Benzenesulfonamide compounds such as flusulfamide;
Oxime ether compounds such as cyflufenamid;
Phenoxyamide compounds such as fenoxanil;
Antibiotics such as validamycin, kasugamycin, polyoxins;
Guanidine compounds such as iminoctadine;

  Other compounds include isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, spiroxamine, chloropicrin, dazomet, Metam-sodium, nicobifen, metrafenone, UBF-307, diclocymet, proquinazid, amisulbrom (aka amibromdole), KIF-7767 (KUF-1204, pyribencarb methyl, mepyricarb), Syngenta 446510 (mandipropamid, dipromandamid), fluopicolide, carpropamid, BCF051, BCM061, BCM062, and the like.

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

  Examples of animal parasite control agents include ectoparasites that parasitize on the body surface of the host animal (back, armpit, lower abdomen, inner thigh, etc.) and the host animal body (stomach, intestinal tract, lung, heart, liver). It is effective for the control of endoparasites parasitizing blood vessels, subcutaneous tissues, lymphoid tissues, etc., among which it is effective for the control of ectoparasites.

  Examples of ectoparasites include animal parasitic mites and fleas. There are so many of these types that it is difficult to list them all.

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

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

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

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

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

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

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

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

Desirable embodiments of the compound represented by the formula (I) are as follows. However, the present invention is not limited to these.
(1) Formula (I):

〔式中、Ｒ¹は水素原子、Ｒ^bで置換されてもよいアルキル、Ｒ^bで置換されてもよいアルケニル、Ｒ^bで置換されてもよいアルキニル、アリール、シアノ、Ｎ＝ＣＨＲ^c、ＯＲ^c、Ｓ(Ｏ)_pＲ^c、ＣＯＳＲ^c、ＣＯＯＲ^c又はＣＯＲ^cであるか、Ｒ¹はアルキル若しくはハロアルキルで置換されてもよい複素環基であり；Ｒ²及びＲ³は各々独立に、水素原子、ハロゲン、シアノ、ニトロ、Ｒ⁸で置換されてもよいアルキル、シクロアルキル、アルケニル、アルキニル、アリール、複素環基、ＮＲ^aＲ^c、ＯＲ^a、ＳＲ^a、ＣＯＲ^a、ＣＯＯＲ^a、ＣＯＮＲ^aＲ^c、ＣＨ＝ＮＯＲ^a、ＳＯ₂Ｒ^a又はＳＯＲ^aであり；Ｒ⁴はトリフルオロメチル又はクロロジフルオロメチルであり；Ｒ⁵は水素原子、ハロゲン、シアノ、ニトロ、Ｒ⁸で置換されてもよいアルキル、Ｒ⁸で置換されてもよいアルケニル、Ｒ⁸で置換されてもよいアルキニル、ＯＲ^a、ＳＲ^a、ＮＲ^aＲ^c、ＣＯＯＲ^a又はＣＯＲ^aであり；Ｒ⁶及びＲ⁷は各々独立に、水素原子、シアノ、アルキル、ハロアルキル又はシクロアルキルであるか、Ｒ⁶とＲ⁷が一緒になってハロゲンで置換されてもよい炭素数３〜６のシクロアルキルを形成してもよく；Ｒ⁸はアルキル、シクロアルキル、アルコキシアルキル、アルコキシアルコキシアルキル、ヒドロキシアルキル、ハロゲン、ハロアルキル、シアノ、ニトロ、ハロゲンで置換されてもよいアリール、ハロゲンで置換されてもよい複素環基、ハロゲンで置換されてもよい複素環オキシ、ＣＯＮＲ^aＲ^c、ＣＯＲ^c、ＣＯＯＲ^c、ＮＲ^aＲ^c又はＯＲ^aであり；Ｒ^aは水素原子、アルキル、シクロアルキル、ハロアルキル又は複素環アルキルであり；Ｒ^bはハロゲン、Ｒ⁸で置換されてもよいアリール、Ｒ⁸で置換されてもよい複素環基、Ｒ⁸で置換されてもよい複素環オキシ、Ｒ⁸で置換されてもよい複素環チオ、シアノ、ＮＲ^aＲ^c、ＮＨＣＯＯＲ^a、ＣＯＲ^c、ＣＯＯＲ^c、ＣＯＮＲ^aＲ^c、アルコキシアルコキシ、ＯＲ^a又はＳ(Ｏ)_pＲ^aであり；Ｒ^cは水素原子、アルキル、ハロアルキル、シクロアルキル、アルコキシアルキル、ヒドロキシアルキル、ハロゲンで置換されてもよいアリール又はハロアルキルで置換されてもよい複素環基であり；ｎは０〜４の整数であり、ｐは０〜２の整数であり、前述した各置換基中のＮＲ^aＲ^c部分は、Ｒ^aとＲ^cが一緒になって、両者が結合する窒素原子とともに５員又は６員の複素環を形成してもよい。但し、N-(2-ピリジルメチル）-3,5,6-トリクロロ-4-(トリフルオロメチル）-2-ピリジルアミンを除く〕で表されるピリジル−メタナミン誘導体又はその塩。

[Wherein, R ¹ is a hydrogen atom, alkyl ^optionally substituted with R ^b , alkenyl optionally substituted with R ^b , alkynyl optionally substituted with R ^b , aryl, cyano, N═CHR ^c , OR ^c , S (O) _p R ^c , COSR ^c , COOR ^c or COR ^c , or R ¹ is a heterocyclic group optionally substituted with alkyl or haloalkyl; R ² and R ³ are each independently Hydrogen atom, halogen, cyano, nitro, alkyl optionally substituted with R ⁸ , cycloalkyl, alkenyl, alkynyl, aryl, heterocyclic group, NR ^a R ^c , OR ^a , SR ^a , COR ^a , COOR ^a , CONR ^a R ^c , CH═NOR ^a , SO ₂ R ^a or SOR ^a ; R ⁴ is trifluoromethyl or chlorodifluoromethyl; R ⁵ is substituted with a hydrogen atom, halogen, cyano, nitro, R ⁸ Moyo Alkyl, alkenyl which may be substituted by R ^8, which may be substituted by R ^{8 alkynyl, OR a, SR a, NR} a R c, be a COOR ^a or COR ^a; R ⁶ and R ⁷ are each independently , A hydrogen atom, cyano, alkyl, haloalkyl or cycloalkyl, or R ⁶ and R ⁷ together may form a cycloalkyl having 3 to 6 carbon atoms which may be substituted with halogen; R ⁸ Is alkyl, cycloalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, halogen, haloalkyl, cyano, nitro, aryl optionally substituted with halogen, heterocyclic group optionally substituted with halogen, halogen substituted Good heterocyclic oxy, CONR ^a R ^c , COR ^c , COOR ^c , NR ^a R ^c or OR ^a ; R ^a is a hydrogen atom, alkyl, Black alkyl, haloalkyl or a heterocyclic alkyl; R ^b is halogen, may be substituted by R ⁸ aryl, which may be substituted by R ⁸ heterocyclic group, which may be substituted by R ⁸ heterocyclyloxy, Heterocyclic thio, cyano, NR ^a R ^c , NHCOOR ^a , COR ^c , COOR ^c , CONR ^a R ^c , alkoxyalkoxy, OR ^a or S (O) _p R ^a optionally substituted by R ⁸ ; R ^c is a hydrogen atom, alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, hydroxyalkyl, aryl optionally substituted with halogen or heterocyclic group optionally substituted with haloalkyl; n is an integer of 0-4; p is an integer of 0 to 2, and the NR ^a R ^c moiety in each substituent described above is a 5- or 6-membered heterocyclic ring together with the nitrogen atom to which R ^a and R ^c are bonded together. Shape It may be. Provided that N- (2-pyridylmethyl) -3,5,6-trichloro-4- (trifluoromethyl) -2-pyridylamine is excluded], or a salt thereof.

(2) R ¹ is a hydrogen atom, alkyl ^optionally substituted with R ^b , alkenyl optionally substituted with R ^b , alkynyl optionally substituted with R ^b , aryl, heterocycle optionally substituted with haloalkyl A group N═CHR ^c , OR ^c , COSR ^c or COR ^c ; R ² and R ³ are each independently a hydrogen atom, halogen, cyano, nitro, alkyl optionally substituted with R ⁸ , cycloalkyl, Alkenyl, alkynyl, aryl, heterocyclic group, NR ^a R ^c , OR ^a , SR ^a , COR ^a , COOR ^a , CONR ^a R ^c , SO ₂ R ^a or SOR ^a ; R ⁵ is a hydrogen atom, halogen, cyano, nitro, optionally substituted by R ⁸ alkyl, COOR ^a or COR ^a; to R ⁶ and R ⁷ are each independently a hydrogen atom, cyano, alkyl, haloalkyl or cycloalkyl; R ⁸ there Kill, cycloalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, halogen, haloalkyl, cyano, nitro, NR ^a R ^c or OR ^a; R ^a is a hydrogen atom, an alkyl, cycloalkyl, or haloalkyl; R ^b There halogen, which may be substituted by R ⁸ aryl, heterocyclic group which may be substituted by R ^{8, cyano, NR a R c, NHCOOR a} , be oR ^a or SR ^a; R ^c is a hydrogen atom, an alkyl , A pyridyl-methanamine derivative or a salt thereof according to (1), which is a heterocyclic group which may be substituted with cycloalkyl, aryl or haloalkyl.

(3) R ² and R ³ are each independently a hydrogen atom, halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, alkynyl, aryl, heterocyclic group, NR ^a R ^c , OR ^a , SR ^a , COR ^a or It is a SOR ^a; R ⁵ is a hydrogen atom, halogen or COR ^a; R ⁸ is alkyl, halogen, haloalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, cyano, NR ^a R ^c or oR ^a; R ^a is hydrogen An atom, alkyl or haloalkyl; R ^b is halogen, aryl, a heterocyclic group optionally substituted by R ⁸ , cyano, NR ^a R ^c , OR ^a or SR ^a ; R ^c is a hydrogen atom, alkyl, The pyridyl-methanamine derivative or a salt thereof according to (2), which is an aryl or heterocyclic group.

(4) R ¹ is a hydrogen atom, alkyl ^optionally substituted with R ^b , alkenyl optionally substituted with R ^b , alkynyl, aryl, heterocyclic group optionally substituted with haloalkyl, OR ^c or COR ^c Yes; R ² is a hydrogen atom, halogen, cyano, alkyl, haloalkyl, alkynyl, aryl, NR ^a R ^c , OR ^a or SR ^a ; R ³ is a hydrogen atom, halogen, cyano, nitro, haloalkyl, aryl, NR ^a R ^c , SR ^a or COR ^a ; R ⁴ is trifluoromethyl; R ⁵ is a hydrogen atom, halogen or COR ^a ; R ⁶ and R ⁷ are each independently a hydrogen atom, alkyl or cyclo R ⁸ is alkyl, halogen, haloalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, cyano or OR ^a ; R ^a is a hydrogen atom or an alkyl; R ^b is halogen, aryl, a heterocyclic group optionally substituted with R ⁸ , OR ^a or NR ^a R ^c ; R ^c is a hydrogen atom, alkyl, aryl or heterocyclic group (2 Pyridyl-methanamine derivatives or salts thereof.

(5) R ¹ is a hydrogen atom, alkyl ^optionally substituted with R ^{b ′} , alkenyl optionally substituted with R ^{b ″} , alkynyl optionally substituted with R ^b , aryl, OR ^c or COR ^c ; R b ^'is halogen, which may be substituted by R ⁸ aryl, cyano, oR ^a or SR ^a; R ^{b "is} halogen, it may be substituted by R ⁸ aryl, optionally substituted by R ⁸ The pyridyl-methanamine derivative or a salt thereof according to (2), which is ^a good heterocyclic group, cyano, OR ^a or SR ^a .

  The pyridyl-methanamine derivative (1) described above or a salt thereof is a novel compound, and the production method [1], production method [2], production method [3], production method [4], production method [5], production method [6], It can manufacture with the manufacturing method containing at least 1 method among the manufacturing methods of the pyridyl-methanamine derivative shown to manufacturing method [7], manufacturing method [8], manufacturing method [9], and manufacturing method [10]. For example, it can manufacture with the manufacturing method containing at least 1 method among the said manufacturing method [1], manufacturing method [2], and manufacturing method [3].

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 Synthesis of N- (2-pyridylmethyl) -6-chloro-4- (trifluoromethyl) -2-pyridylamine (Compound No. 128) 2,6-Dichloro-4- (trifluoromethyl) pyridine 10 g of 2-picolylamine was added to 10 g of ethanol in 50 ml, and the mixture was stirred at room temperature for 24 hours, followed by reaction at 60 ° C. for 16 hours and at 80 ° C. for 24 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, ethyl acetate was added to the residue, and the ethyl acetate solution was washed with saturated brine and dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure. The obtained solid residue was recrystallized from hexane to obtain 9.55 g of the desired product.

Synthesis Example 2 Synthesis of N- (2-pyridylmethyl) -5,6-dichloro-4- (trifluoromethyl) -2-pyridylamine (Compound No. 118) N- (2-pyridylmethyl) -6-chloro To a solution of 5.0 g of -4- (trifluoromethyl) -2-pyridylamine in 50 ml of dimethylformamide, 2.4 g of N-chlorosuccinimide was added at room temperature and gradually heated to 50 ° C. After 3 hours, 0.2 g of N-chlorosuccinimide was added and reacted for 1 hour, and then 0.2 g was added and reacted for 45 minutes. After allowing to cool, water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 2.8 g of the desired product.

Synthesis Example 3 Synthesis of N-allyl-N- (2-pyridylmethyl) -5,6-dichloro-4- (trifluoromethyl) -2-pyridylamine (Compound No. 55) N- (2-pyridylmethyl) To a solution of 300 mg of -5,6-dichloro-4- (trifluoromethyl) -2-pyridylamine in 4 ml of dimethylformamide, 40 mg of sodium hydride was added and stirred at room temperature. After 10 minutes, 110 mg of allyl bromide was added dropwise and stirred at room temperature for 2.5 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 3/1) to obtain 150 mg of the desired product.

Synthesis Example 4 Synthesis of N, N-bis (2-pyridylmethyl) -5-nitro-4- (trifluoromethyl) -2-pyridylamine (Compound No. 9) (1) To 5 ml of 97% sulfuric acid under ice-cooling 1.0 g of 2-amino-4- (trifluoromethyl) pyridine was added in portions and stirred at room temperature until dissolved. The reaction solution was cooled to −10 ° C., and a mixed solution of cooled 69% nitric acid 0.8 ml and 97% sulfuric acid 0.6 ml was added dropwise and reacted at −10 ° C. for 30 minutes. The reaction solution was poured into 40 g of ice and neutralized by adding 28% aqueous ammonia. After stirring, the precipitated crystals were collected by filtration and dried. The obtained colorless powder was added to 5.5 ml of 97% sulfuric acid under ice cooling and stirred for 30 minutes. Furthermore, after stirring at room temperature for 1 hour, it was made to react at 50 degreeC for 1 hour. After cooling, the reaction solution was poured into 40 g of ice, neutralized by adding 28% aqueous ammonia, and stirred under ice cooling. The precipitated crystals were collected by filtration, washed with cold water, and dried to obtain 0.41 g of 2-amino-5-nitro-4- (trifluoromethyl) pyridine having a melting point of 138-140 ° C.

(2) To a solution of 260 mg of 2-amino-5-nitro-4- (trifluoromethyl) pyridine and 350 mg of (2-bromomethyl) pyridine hydrobromide in 6 ml of dimethyl sulfoxide, 0.38 ml of 10M sodium hydroxide aqueous solution was added dropwise. And allowed to react for 16 hours at room temperature. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/2) to obtain 130 mg of the desired product.

Synthesis Example 5 Synthesis of N, N-bis (2-pyridylmethyl) -6-bromo-4- (trifluoromethyl) -2-pyridylamine (Compound No. 90) (1) 2,6-Dichloro-4- To 5.0 g of (trifluoromethyl) pyridine, 25 ml of a hydrogen bromide saturated acetic acid solution (about 30%) was added and reacted under reflux. After 3 hours, 10 ml of a hydrogen bromide saturated acetic acid solution (about 30%) was added, and the mixture was refluxed for 2 hours. Further, 10 ml of a hydrogen bromide saturated acetic acid solution (about 30%) was added, and after refluxing for 2 hours, 10 ml of a hydrogen bromide saturated acetic acid solution (about 30%) was added and refluxed for 1 hour. After cooling the reaction solution to room temperature, it was added to 200 ml of a 10% aqueous sodium hydroxide solution under ice cooling, and sodium hydroxide (solid) was added to the resulting solution to make it basic. Extraction was performed twice with diethyl ether, the extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 6.9 g of oily 2,6-dibromo-4- (trifluoromethyl) pyridine.

(2) To a solution of 1.0 g of 2,6-dibromo-4- (trifluoromethyl) pyridine in 10 ml of dimethylformamide, 0.72 g of 2,2′-dipicolylamine and 0.33 g of sodium hydrogen carbonate were added, and 90 ° C. For 19 hours. After allowing to cool, water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/3) to obtain 1.1 g of the desired product.

Synthesis Example 6 Synthesis of N, N-bis (2-pyridylmethyl) -6-bromo-5-chloro-4- (trifluoromethyl) -2-pyridylamine (Compound No. 92) N, N-bis (2 -Pyridylmethyl) -6-bromo-4- (trifluoromethyl) -2-pyridylamine (500 mg) in dimethylformamide (5 ml) was added with 170 mg of N-chlorosuccinimide and reacted at 60 ° C. for 7 hours. After allowing to cool, water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/3) to obtain 500 mg of the desired product.

Synthesis Example 7 Synthesis of N, N-bis (2-pyridylmethyl) -5-chloro-6-ethynyl-4- (trifluoromethyl) -2-pyridylamine (Compound No. 94) N, N-bis (2 -Pyridylmethyl) -6-bromo-5-chloro-4- (trifluoromethyl) -2-pyridylamine 370 mg, trimethylsilylacetylene 95 mg, trans-dichlorobistriphenylphosphine palladium 20 mg, copper iodide 10 mg and triethylamine 4 ml for 4 hours Refluxed. Triethylamine was distilled off under reduced pressure, water was added, and the mixture was filtered through celite. The filtrate was extracted twice with diethyl ether, and the extraction solvent was distilled off under reduced pressure. 2 ml of methanol and 4 ml of 1N aqueous sodium hydroxide solution were added to the residue, and the mixture was stirred at room temperature for 2 hours and acidified with 10% hydrochloric acid. Methanol was distilled off under reduced pressure, and the mixture was basified with sodium carbonate, extracted twice with diethyl ether, the extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/3) to obtain 250 mg of the desired product.

Synthesis Example 8 Synthesis of N- (1- (3-pyridyl) ethyl) -N- (2-pyridylmethyl) -5,6-dichloro-4-trifluoromethyl-2-pyridylamine (Compound No. 97) 1) After adding 3.4 g of N-chlorosuccinimide to a mixed solution of 4.56 g of 2-amino-6-chloro-4-trifluoromethylpyridine and 30 ml of dimethylformamide, the mixed solution was heated to 80 ° C. for 2 hours. Reacted. After completion of the reaction, the mixed solution was ice-cooled and a saturated aqueous sodium hydrogen carbonate solution was added. After extracting twice with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent of the organic layer was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 3/1) to give 6-amino-2,3- 3.8 g of dichloro-4-trifluoromethylpyridine was obtained.

(2) 557 mg of 3-pyridinealdehyde, 3 g of molecular sieves and 0.5 ml of acetic acid were added to a mixed solution of 800 mg of 6-amino-2,3-dichloro-4-trifluoromethylpyridine and 20 ml of ethanol, and reacted for 3 days under reflux. It was. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in 50 ml of ether, and 4.6 ml of methylmagnesium bromide solution (3M, ether solution) was added dropwise under ice cooling. After completion of dropping, the mixture was stirred overnight at room temperature. The mixed solution was ice-cooled, and 20 ml of water was added. After extraction twice with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent of the organic layer was distilled off under reduced pressure, the residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/1), and the resulting crude crystals were recrystallized from ethyl acetate-hexane. As a result, 308 mg of N- (1- (3-pyridyl) ethyl) -5,6-dichloro-4-trifluoromethyl-2-pyridylamine having a melting point of 159 to 161 ° C. was obtained.

(3) N- (1- (3-pyridyl) ethyl) -5,6-dichloro-4-trifluoromethyl-2-pyridylamine was added to a suspension of 19 mg of sodium hydride and 10 ml of dimethylformamide under ice cooling. A mixed solution of 133 mg and 1 ml of dimethylformamide was gradually added dropwise, followed by stirring at 0 ° C. for 30 minutes. Subsequently, a mixed solution of 136 mg of 2-bromomethylpyridine and 2 ml of dimethylformamide was gradually added dropwise. After completion of dropping, the mixed solution was reacted at room temperature for 2 hours. After completion of the reaction, the mixed solution was ice-cooled, 10 ml of water was added, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent of the organic layer was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 111 mg of the desired product as a colorless oil.

Synthesis Example 9 Synthesis of N, N-bis (2-pyridylmethyl) -5-chloro-4,6-bis (trifluoromethyl) -2-pyridylamine (Compound No. 103) (1) 2-Amino-4 After adding 870 mg of N-chlorosuccinimide to 5 ml of dimethylformamide in 1.5 g of 1,6-bis (trifluoromethyl) pyridine, the mixed solution was heated to 40 ° C. and reacted for 1 hour. After allowing to cool, water was added and the mixture was stirred and extracted twice with ethyl acetate, and then the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent of the organic layer was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 7/3), and 2-amino-5-chloro-4, melting point 97 ° C. 1.1 g of 6-bis (trifluoromethyl) pyridine was obtained.

(2) 0.2 ml of 10M aqueous sodium hydroxide solution in 150 ml of 2-amino-5-chloro-4,6-bis (trifluoromethyl) pyridine and 260 mg of 2-bromomethylpyridine hydrobromide in 4 ml of dimethyl sulfoxide Was added dropwise and reacted at room temperature for 2.5 hours. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/3) to obtain 110 mg of the desired product.

Synthesis Example 10 Synthesis of N- (1- (2-pyridyl) -2-methyl) propyl-5,6-dichloro-4-trifluoromethyl-2-pyridylamine (Compound No. 75) 6-amino-2, A catalytic amount of acetic acid was added to a mixed solution of 313 mg of 3-dichloro-4- (trifluoromethyl) pyridine, 160 mg of 2-pyridinealdehyde and 10 ml of methanol, and reacted under reflux. After 6 hours, the solvent was distilled off under reduced pressure, and 30 ml of ether was added to the resulting oily residue. To this solution, 2.7 ml of an ether solution of isopropylmagnesium chloride (2M) was added dropwise under ice-cooling. After completion of the dropwise addition, the mixture was warmed to room temperature and stirred overnight. Water was added to the reaction solution, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/4) to obtain 182 mg of the desired product having a melting point of 165-168 ° C.

Synthesis Example 11 Synthesis of N- (2-pyridylmethyl) -5-cyano-4,6-bis (trifluoromethyl) -2-pyridylamine (Compound No. 286) (1) 6-amino-3-bromo- To a solution of 1.4 g of 2,4-bis (trifluoromethyl) pyridine in 3 ml of hexamethylphosphoric triamide, 1.0 g of copper cyanide was added and reacted at 140 ° C. for 4 hours under microwave irradiation. After allowing to cool, water and ethyl acetate were added to the reaction solution, and the insoluble solid was filtered through Celite. The organic layer was separated and the aqueous layer was further extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: n-hexane / ethyl acetate = 1/2) and 690 mg of 6-amino-3-cyano-2,4-bis (trifluoromethyl) pyridine having a melting point of 158-160 ° C. Got.

(2) To a mixed solution of 350 mg of 6-amino-3-cyano-2,4-bis (trifluoromethyl) pyridine and 4 ml of ethanol, 150 mg of 2-pyridinealdehyde, 0.4 g of molecular sieve and 0.1 ml of acetic acid were added, The reaction was carried out for 40 hours under reflux. After completion of the reaction, the mixture was filtered and the solvent was distilled off under reduced pressure. The residue was dissolved in 4 ml of ethanol, 52 mg of sodium borohydride was added under ice cooling, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 20 ml of water was added and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent of the organic layer was distilled off under reduced pressure, and the residue was purified by silica gel flash chromatography to obtain 82 mg of the desired product having a melting point of 122-123 ° C.

Synthesis Example 12 Synthesis of N, N-bis (2-pyridylmethyl) -6-chloro-5-cyano-4- (trifluoromethyl) -2-pyridylamine hydrochloride (Compound No. 330) N, N-bis To a solution of 350 mg of (2-pyridylmethyl) -6-chloro-5-cyano-4- (trifluoromethyl) -2-pyridylamine (Compound No. 24) in 7 ml of ethanol, 1.5 ml of concentrated hydrochloric acid was added dropwise. After stirring at room temperature for 1 hour, the solvent was distilled off under reduced pressure, and the resulting white solid was repulped with ethanol to obtain 410 mg of the desired product having a melting point of 144-146 ° C.

Next, typical examples of the compound represented by the formula (I) are listed in Table 1. These compounds can be synthesized based on various production methods of the compounds represented by the above Synthesis Examples 1 to 12 or the aforementioned formula (I). In Table 1, No. indicates compound No., Me is methyl, Et is ethyl, Pr (i) is isopropyl, Bu (t) is tertiary butyl, CO is carbonyl, COO is carboxyl, Ph is phenyl, pyridyl represents pyridyl, pyridyloxy represents pyridyloxy, piperidino represents piperidino, and morpholinyl represents morpholinyl. The temperature indicated as a physical property is the melting point, oil indicates an oily substance, amorphous indicates an amorphous substance, and gummy oil indicates a sticky oily substance. ND represents a refractive index. For those for which the melting point or refractive index is not shown, ¹ H-NMR is shown in Table 2.

Next, test examples are described.
Test Example 1 Effect test on peach aphid Japanese radish leaves were inserted into a test tube containing water, and about 20 first-instar larvae were released on the leaves. The next day, after counting the number of larvae parasitic on the radish leaves, the parasitic radish leaves were immersed in a chemical solution adjusted to a concentration of 800 ppm of the present compound for about 10 seconds. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Five days after the treatment, the viability of the peach aphid was determined, and the mortality rate was determined by the following formula. The detached insects and abnormal insects were regarded as dead insects. Compound No. 1, 2, 4, 6, 9, 10, 13, 16, 17, 18, 19, 20, 22, 24, 27, 32, 34, 35, 38, 40, 42, 43, 45, 48, 53-55, 57, 62-64, 68, 70, 71, 73, 74, 77-81, 83, 86-107, 112, 114, 116-118, 121, 123, 124, 128, 133, 134, 136, 137, 139-142, 145-149, 151, 152, 154, 155, 157, 161, 162, 164, 165, 167, 168, 173-175, 177, 178, 182-186, 191, 192, 200-206, 208, 210, 211, 213-215, 217-220, 222, 223, 225-230, 231, 233-235, 239, 240, 24 2, 248, 255-264, 270, 271, 280, 284, 287, 288, 290-293, 295, 297-300, 303, 304, 306-314, 316-321, 329, 331 and 332 As a result, all compounds showed a death rate of 90% or more.
Death rate (%) = (1− (number of surviving insects / number of treated insects)) × 100

Test Example 2 Effect test on Japanese pearl moth A cabbage leaf piece was immersed for about 10 seconds in a chemical solution prepared so that the concentration of the compound of the present invention was 800 ppm and air-dried. A moist filter paper was laid on a petri dish having a diameter of 9 cm, and an air-dried piece of cabbage was placed on the filter paper. There, 10 larvae of 2 to 3 years old were released, covered and left in a constant temperature room at 25 ° C. On the 5th day after the release, the mortality was determined, and the mortality was determined by the following formula. Abnormal insects were considered dead. Compound No. 1, 2, 4, 6, 9-11, 16, 17, 19, 20, 22-24, 42, 43, 45, 48, 50, 53-57, 59, 63, 64, 67- 71, 73, 74, 76, 77, 79, 80, 83, 86, 89, 92, 93, 95-100, 102, 103, 105, 106, 109, 112, 114, 116-118, 121, 124, 125, 133, 135, 137, 139, 140, 142, 145-149, 151, 154, 155, 157, 161, 162, 164-168, 173-180, 182-186, 191, 192, 194, 198, 201, 202, 204-208, 210, 211, 213, 214, 217-225, 228, 229, 231-235, 238-240, 242, 248, 250, 251, 252, 255-257, 259-263, 266, 270, 277, 280, 285, 287-293, 295, 297-300, 303-306, 308-314, 316-321, 326, 327, 329, When 331 and 332 were tested, all the compounds showed a death rate of 90% or more.
Death rate (%) = (Number of dead insects / Number of dead insects) × 100

Test Example 3 Nile spider mite insecticide test A drug solution prepared so that the concentration of the compound of the present invention was 800 ppm was prepared. Only one primary kidney bean leaf was left and transplanted to a pot (diameter 8 cm, height 7 cm), and 20 adult nymph spider mites were released. This was dipped in the above chemical solution together with green beans, air-dried, and left in a constant temperature room at 25 ° C. with illumination. Life or death was determined on the second or third day after the treatment, and the killing rate was determined by the following formula. The detached adults and abnormal insects were regarded as dead. Compound Nos. 1-4, 6, 9, 10, 13, 16-19, 24, 27, 35, 42, 43, 45, 48, 53-55, 57, 62-64, 68, 70-74, 77-80, 83, 86-90, 92-107, 109, 110, 112, 114, 116, 118, 121, 133-135, 137, 139, 140, 141, 142, 146-149, 151, 152, 154, 155, 157, 161, 162, 164-168, 171, 173-176, 180-187, 191-193, 196, 198, 199-201, 204-206, 208, 210, 211, 213-215, 217-223, 225-228, 230, 231, 234-236, 240-242, 248, 255-263, 270, 271, 272, 279, When 280, 284, 285, 287-293, 295, 297-300, 303-306, 308-314, 316-321, 324-326, 329, 331 and 332 were tested, all the compounds were 90% or more. The rate of adult worms was shown.
Morbidity rate (%) = (number of dead ticks / number of treated ticks) × 100

Test Example 4 Medicinal Efficacy Test for Phytophthora tick 1 ml (concentration: 10 μg / ml) of an acetone solution of the compound of the present invention is dropped on the inner surface of a 9 cm petri dish with a micropipette. After the petri dish inner surface is dried, 60 to 180 juvenile mites are put, covered with a polyethylene sheet and sealed with a rubber band. When the number of rollover (knockdown) ticks after drug contact is observed, the compound of the present invention rolls over most of the ticklet ticks.

Test Example 5 Medicinal effect test using dogs against winged tick 50 young ticks of winged tick are released into the ears of dogs (beagle, 8 months old) and artificially parasitized. After counting mites that have settled 2 days after the infestation, the compound of the present invention formulated on the back of the neck is spot-on at a dose of 10 mg / kg. Observation is carried out until the fifth day after drug administration, and the number of infestations, the number of drops, and the life and death of the fallen spider mites are observed. Dogs are kept individually in cages, tap water is freely taken, and a predetermined amount of feed for dogs is given once a day. As a result, the compound of the present invention drops or kills the parasitic spider mite.

Test Example 6 Medicinal Efficacy Test Using Dogs for Cat Fleas 100 cat flea non-blood-sucking adults within 3 days after emergence were released on the back coat of dogs (beagle, 8 months old), artificially infested, and formulated into the back of the neck Inventive compounds are spotted on at a dose of 10 mg / kg. On the third day after drug administration, collect the cat fleas using a flea comb and examine the number of colonies. Dogs are kept individually in cages, tap water is freely taken, and a predetermined amount of feed for dogs is given once a day. As a result, the compound of the present invention suppresses the establishment of cat fleas.

Next, formulation examples are described.
Formulation Example 1
(1) Compound of the present invention 20 parts by weight (2) Clay 70 parts by weight (3) White carbon 5 parts by weight (4) Sodium polycarboxylate 3 parts by weight (5) Sodium alkylnaphthalene sulfonate 2 parts by weight or more To make a wettable powder.
Formulation Example 2
(1) Compound of the present invention 5 parts by weight (2) Talc 60 parts by weight (3) Calcium carbonate 34.5 parts by weight (4) Liquid paraffin 0.5 parts by weight or more are uniformly mixed to obtain a powder.
Formulation Example 3
(1) Compound of the present invention 20 parts by weight (2) N, N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene tristyryl phenyl ether 10 parts by weight (4) Calcium dodecylbenzenesulfonate 2 parts by weight (5) Xylene 48 A mixture of more than parts by weight is uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 4
(1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight A mixture of each component and the present compound Mix at a weight ratio of 4: 1 to make a wettable powder.
Formulation Example 5
(1) Compound of the present invention 50 parts by weight (2) Sodium alkylnaphthalene sulfonate formaldehyde condensate 2 parts by weight (3) Silicone oil 0.2 parts by weight (4) Water 47.8 parts by weight or more uniformly mixed (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are further added to the crushed stock solution, and the mixture is uniformly mixed, granulated and dried to obtain a granulated wettable powder.

Formulation Example 6
(1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene alkyl ether phosphate 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1 ) To (3) are uniformly mixed in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove acetone and form granules.
Formulation Example 7
(1) Compound of the present invention 2.5 parts by weight (2) N, N-dimethylacetamide 2.5 parts by weight (3) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved to give a trace amount of spray ( ultra low volume formulation).

Formulation Example 8
(1) Compound of the present invention 40 parts by weight (2) Polyoxyethylene tristyryl phenyl ether potassium phosphate 4 parts by weight (3) Silicone oil 0.2 part by weight (4) Xanthan gum 0.1 part by weight (5) Ethylene glycol 5 Part by weight (6) Water 50.7 parts by weight or more are uniformly mixed and pulverized to obtain an aqueous suspension.
Formulation Example 9
(1) Compound of the present invention 10 parts by weight (2) 80 parts by weight of diethylene glycol monoethyl ether (3) Polyoxyethylene alkyl ether 10 parts by weight or more of ingredients are mixed uniformly to obtain an aqueous solution.

Claims (10)

Formula (I):

[Wherein, R ¹ is a hydrogen atom, alkyl ^optionally substituted with R ^b , alkenyl optionally substituted with R ^b , alkynyl optionally substituted with R ^b , aryl, cyano, N═CHR ^c , OR ^c , S (O) _p R ^c , COSR ^c , COOR ^c or COR ^c , or R ¹ is a heterocyclic group optionally substituted with alkyl or haloalkyl; R ² and R ³ are each independently Hydrogen atom, halogen, cyano, nitro, alkyl optionally substituted with R ⁸ , cycloalkyl, alkenyl, alkynyl, aryl, heterocyclic group, NR ^a R ^c , OR ^a , SR ^a , COR ^a , COOR ^a , CONR ^a R ^c , CH═NOR ^a , SO ₂ R ^a or SOR ^a ; R ⁴ is trifluoromethyl or chlorodifluoromethyl; R ⁵ is substituted with a hydrogen atom, halogen, cyano, nitro, R ⁸ Moyo Alkyl, alkenyl which may be substituted by R ^8, which may be substituted by R ^{8 alkynyl, OR a, SR a, NR} a R c, be a COOR ^a or COR ^a; R ⁶ and R ⁷ are each independently , A hydrogen atom, cyano, alkyl, haloalkyl or cycloalkyl, or R ⁶ and R ⁷ together may form a cycloalkyl having 3 to 6 carbon atoms which may be substituted with halogen; R ⁸ Is alkyl, cycloalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, halogen, haloalkyl, cyano, nitro, aryl optionally substituted with halogen, heterocyclic group optionally substituted with halogen, halogen substituted Good heterocyclic oxy, CONR ^a R ^c , COR ^c , COOR ^c , NR ^a R ^c or OR ^a ; R ^a is a hydrogen atom, alkyl, Black alkyl, haloalkyl or a heterocyclic alkyl; R ^b is halogen, may be substituted by R ⁸ aryl, which may be substituted by R ⁸ heterocyclic group, which may be substituted by R ⁸ heterocyclyloxy, Heterocyclic thio, cyano, NR ^a R ^c , NHCOOR ^a , COR ^c , COOR ^c , CONR ^a R ^c , alkoxyalkoxy, OR ^a or S (O) _p R ^a optionally substituted by R ⁸ ; R ^c is a hydrogen atom, alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, hydroxyalkyl, aryl optionally substituted with halogen or heterocyclic group optionally substituted with haloalkyl; n is an integer of 0-4; p is an integer of 0 to 2, and the NR ^a R ^c moiety in each substituent described above is a 5- or 6-membered heterocyclic ring together with the nitrogen atom to which R ^a and R ^c are bonded together. Shape It may be. Provided that N- (2-pyridylmethyl) -3,5,6-trichloro-4- (trifluoromethyl) -2-pyridylamine is excluded], or a salt thereof. R ¹ is a hydrogen atom, alkyl ^optionally substituted with R ^b , alkenyl optionally substituted with R ^b , alkynyl optionally substituted with R ^b , aryl, heterocyclic group optionally substituted with haloalkyl, N = CHR ^c , OR ^c , COSR ^c or COR ^c ; R ² and R ³ are each independently a hydrogen atom, halogen, cyano, nitro, alkyl optionally substituted with R ⁸ , cycloalkyl, alkenyl, alkynyl , Aryl, heterocyclic group, NR ^a R ^c , OR ^a , SR ^a , COR ^a , COOR ^a , CONR ^a R ^c , SO ₂ R ^a or SOR ^a ; R ⁵ is a hydrogen atom, halogen, cyano, nitro , which may be substituted by R ⁸ alkyl, COOR ^a or COR ^a; R ⁶ and independently R ⁷ are each a hydrogen atom, cyano, alkyl, haloalkyl or cycloalkyl; R ⁸ is alkyl Cycloalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, halogen, haloalkyl, cyano, nitro, NR ^a R ^c or OR ^a; R ^a is a hydrogen atom, an alkyl, cycloalkyl, or haloalkyl; R ^b is halogen , which may be substituted by R ⁸ aryl, heterocyclic group which may be substituted by R ^8, cyano, ^{NR a R c, NHCOOR a,} oR a or SR ^a; R ^c is a hydrogen atom, an alkyl, cycloalkyl The pyridyl-methanamine derivative or a salt thereof according to claim 1, which is a heterocyclic group which may be substituted with alkyl, aryl or haloalkyl. R ² and R ³ are each independently a hydrogen atom, halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, alkynyl, aryl, heterocyclic group, NR ^a R ^c , OR ^a , SR ^a , COR ^a or SOR ^a R ⁵ is a hydrogen atom, halogen or COR ^a ; R ⁸ is alkyl, halogen, haloalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, cyano, NR ^a R ^c or OR ^a ; R ^a is a hydrogen atom, alkyl Or R ^b is halogen, aryl, a heterocyclic group optionally substituted with R ⁸ , cyano, NR ^a R ^c , OR ^a or SR ^a ; R ^c is a hydrogen atom, alkyl, aryl or hetero The pyridyl-methanamine derivative or a salt thereof according to claim 2, which is a cyclic group. R ¹ is a hydrogen atom, alkyl ^optionally substituted with R ^b , alkenyl optionally substituted with R ^b , alkynyl, aryl, heterocyclic group optionally substituted with haloalkyl, OR ^c or COR ^c ; R ² is a hydrogen atom, halogen, cyano, alkyl, haloalkyl, alkynyl, aryl, NR ^a R ^c , OR ^a or SR ^a ; R ³ is a hydrogen atom, halogen, cyano, nitro, haloalkyl, aryl, NR ^a R ^c , be a SR ^a or COR ^a; R ⁴ is trifluoromethyl; R ⁵ is a hydrogen atom, a halogen or be a COR ^a; to R ⁶ and R ⁷ are each independently hydrogen atom, alkyl or cycloalkyl R ⁸ is alkyl, halogen, haloalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, cyano or OR ^a ; R ^a is a hydrogen atom or alkyl; There; R ^b is halogen, aryl, optionally substituted heterocyclic group R ^8, be a OR ^a, or NR ^a R ^c; R ^c is a hydrogen atom, an alkyl, in claim 2 is an aryl or heterocyclic group The pyridyl-methanamine derivative or a salt thereof described. Formula (I):

[Wherein, R ¹ is a hydrogen atom, alkyl ^optionally substituted with R ^b , alkenyl optionally substituted with R ^b , alkynyl optionally substituted with R ^b , aryl, cyano, N═CHR ^c , OR ^c , S (O) _p R ^c , COSR ^c , COOR ^c or COR ^c , or R ¹ is a heterocyclic group optionally substituted with alkyl or haloalkyl; R ² and R ³ are each independently Hydrogen atom, halogen, cyano, nitro, alkyl optionally substituted with R ⁸ , cycloalkyl, alkenyl, alkynyl, aryl, heterocyclic group, NR ^a R ^c , OR ^a , SR ^a , COR ^a , COOR ^a , CONR ^a R ^c , CH═NOR ^a , SO ₂ R ^a or SOR ^a ; R ⁴ is trifluoromethyl or chlorodifluoromethyl; R ⁵ is substituted with a hydrogen atom, halogen, cyano, nitro, R ⁸ Moyo Alkyl, alkenyl which may be substituted by R ^8, which may be substituted by R ^{8 alkynyl, OR a, SR a, NR} a R c, be a COOR ^a or COR ^a; R ⁶ and R ⁷ are each independently , A hydrogen atom, cyano, alkyl, haloalkyl or cycloalkyl, or R ⁶ and R ⁷ together may form a cycloalkyl having 3 to 6 carbon atoms which may be substituted with halogen; R ⁸ Is alkyl, cycloalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, halogen, haloalkyl, cyano, nitro, aryl optionally substituted with halogen, heterocyclic group optionally substituted with halogen, halogen substituted Good heterocyclic oxy, CONR ^a R ^c , COR ^c , COOR ^c , NR ^a R ^c or OR ^a ; R ^a is a hydrogen atom, alkyl, Black alkyl, haloalkyl or a heterocyclic alkyl; R ^b is halogen, may be substituted by R ⁸ aryl, which may be substituted by R ⁸ heterocyclic group, which may be substituted by R ⁸ heterocyclyloxy, Heterocyclic thio, cyano, NR ^a R ^c , NHCOOR ^a , COR ^c , COOR ^c , CONR ^a R ^c , alkoxyalkoxy, OR ^a or S (O) _p R ^a optionally substituted by R ⁸ ; R ^c is a hydrogen atom, alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, hydroxyalkyl, aryl optionally substituted with halogen or heterocyclic group optionally substituted with haloalkyl; n is an integer of 0-4; p is an integer of 0 to 2, and the NR ^a R ^c moiety in each substituent described above is a 5- or 6-membered heterocyclic ring together with the nitrogen atom to which R ^a and R ^c are bonded together. Shape It may be. However, N- (2-pyridylmethyl) -3,5,6-trichloro-4- (trifluoromethyl) -2-pyridylamine is excluded]. (1) Formula (II):

Wherein R ² , R ³ , R ⁴ and R ⁵ are as described above and X is a halogen, and the formula (III):

(Wherein R ¹ , R ⁶ , R ⁷ , R ⁸ and n are as defined above) or (2) Formula (V-1):

(Wherein, R ^1a is optionally substituted by R ^b alkyl, alkenyl which may be substituted with R ^b, alkynyl which may be substituted by R ^b, aryl, optionally substituted with alkyl or haloalkyl complex A cyclic group, N = CHR ^c , OR ^c , S (O) _p R ^c , COSR ^c , COOR ^c or COR ^c , wherein R ^b, R ^c , p, R ² , R ³ , R ⁴ and R ⁵ are A compound represented by formula (VI):

(Wherein R ⁶ , R ⁷ , R ⁸ , X and n are as described above) or (3) Formula (I-1):

(Wherein R ² , R ³ , R ^4, R ⁵ , R ⁶ , R ⁷ , R ⁸ and n are as defined above) and the formula (VII): R ^1a -X ( Wherein R ^1a and X are the same as defined above). Formula (I):

[Wherein, R ¹ is a hydrogen atom, alkyl ^optionally substituted with R ^b , alkenyl optionally substituted with R ^b , alkynyl optionally substituted with R ^b , aryl, cyano, N═CHR ^c , OR ^c , S (O) _p R ^c , COSR ^c , COOR ^c or COR ^c , or R ¹ is a heterocyclic group optionally substituted with alkyl or haloalkyl; R ² and R ³ are each independently Hydrogen atom, halogen, cyano, nitro, alkyl optionally substituted with R ⁸ , cycloalkyl, alkenyl, alkynyl, aryl, heterocyclic group, NR ^a R ^c , OR ^a , SR ^a , COR ^a , COOR ^a , CONR ^a R ^c , CH═NOR ^a , SO ₂ R ^a or SOR ^a ; R ⁴ is trifluoromethyl or chlorodifluoromethyl; R ⁵ is substituted with a hydrogen atom, halogen, cyano, nitro, R ⁸ Moyo Alkyl, alkenyl which may be substituted by R ^8, which may be substituted by R ^{8 alkynyl, OR a, SR a, NR} a R c, be a COOR ^a or COR ^a; R ⁶ and R ⁷ are each independently , A hydrogen atom, cyano, alkyl, haloalkyl or cycloalkyl, or R ⁶ and R ⁷ together may form a cycloalkyl having 3 to 6 carbon atoms which may be substituted with halogen; R ⁸ Is alkyl, cycloalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, halogen, haloalkyl, cyano, nitro, aryl optionally substituted with halogen, heterocyclic group optionally substituted with halogen, halogen substituted Good heterocyclic oxy, CONR ^a R ^c , COR ^c , COOR ^c , NR ^a R ^c or OR ^a ; R ^a is a hydrogen atom, alkyl, Black alkyl, haloalkyl or a heterocyclic alkyl; R ^b is halogen, may be substituted by R ⁸ aryl, which may be substituted by R ⁸ heterocyclic group, which may be substituted by R ⁸ heterocyclyloxy, Heterocyclic thio, cyano, NR ^a R ^c , NHCOOR ^a , COR ^c , COOR ^c , CONR ^a R ^c , alkoxyalkoxy, OR ^a or S (O) _p R ^a optionally substituted by R ⁸ ; R ^c is a hydrogen atom, alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, hydroxyalkyl, aryl optionally substituted with halogen or heterocyclic group optionally substituted with haloalkyl; n is an integer of 0-4; p is an integer of 0 to 2, and the NR ^a R ^c moiety in each substituent described above is a 5- or 6-membered heterocyclic ring together with the nitrogen atom to which R ^a and R ^c are bonded together. Shape Pesticide with methanamine derivative or a salt thereof as an active ingredient - pyridyl represented by and may be]. R ¹ is a hydrogen atom, alkyl ^optionally substituted with R ^b , alkenyl optionally substituted with R ^b , alkynyl optionally substituted with R ^b , aryl, heterocyclic group optionally substituted with haloalkyl, N = CHR ^c , OR ^c , COSR ^c or COR ^c ; R ² and R ³ are each independently a hydrogen atom, halogen, cyano, nitro, alkyl optionally substituted with R ⁸ , cycloalkyl, alkenyl, alkynyl , Aryl, heterocyclic group, NR ^a R ^c , OR ^a , SR ^a , COR ^a , COOR ^a , CONR ^a R ^c , SO ₂ R ^a or SOR ^a ; R ⁵ is a hydrogen atom, halogen, cyano, nitro , which may be substituted by R ⁸ alkyl, COOR ^a or COR ^a; R ⁶ and independently R ⁷ are each a hydrogen atom, cyano, alkyl, haloalkyl or cycloalkyl; R ⁸ is alkyl Substituted with R ^b is halogen, aryl which may be substituted with R ^8, R ^8; cycloalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, hydroxyalkyl, halogen, haloalkyl, cyano, nitro, NR ^a R be ^c or OR ^a An optionally substituted heterocyclic group, cyano, NR ^a R ^c , NHCOOR ^a , OR ^a or SR ^a ; wherein R ^c is ^a heterocyclic group optionally substituted by a hydrogen atom, alkyl, cycloalkyl, aryl or haloalkyl The pest control agent according to claim 6.   A pesticide for agricultural and horticultural use containing the pyridyl-methanamine derivative represented by the formula (I) according to claim 6 or a salt thereof as an active ingredient.   An insecticide, acaricide or nematicide containing a pyridyl-methanamine derivative represented by the formula (I) according to claim 6 or a salt thereof as an active ingredient.   A method for controlling pests by applying an effective amount of a pyridyl-methanamine derivative represented by the formula (I) according to claim 6 or a salt thereof.