JP2007051105A - Difluoroalkane amide-based compound, method for producing the same, and noxious organism exterminating agent containing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new noxious organism exterminating agent scarcely having such defects that efficacy of conventional noxious organism exterminating agents is not enough and use thereof is restricted because the noxious organism acquires resistance thereto, while many of the conventional agents which are used for a long period cause the above problems and have various other problems to be solved. <P>SOLUTION: This noxious organism exterminating agent contains a difluoroalkane amide-based compound expressed formula (I) [X<SP>1</SP>and X<SP>2</SP>are each H, a halogen or the like; Y is an alkyl; G<SP>1</SP>and G<SP>2</SP>are each H, Q (Q is an alkyl which may be substituted, a cycloalkyl which may be substituted or the like) or the like; A is O or S; and n is 1 to 10] or a salt thereof as an active ingredient. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a novel difluoroalkanamide compound useful as an active ingredient of a pest control agent.

  EP 661289 and EP 428661 disclose difluoroalkane ester compounds. However, there is no description of difluoroalkanamide compounds of the formula (I) described later.

European Publication No. 661289 European Publication No. 432861

  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 difluoroalkanamide compounds in order to find a better pest control agent. As a result, it has been found that the novel difluoroalkanamide compound has a very high control effect against pests at a low dosage, and also has safety against crops, pest natural enemies or mammals, The present invention has been completed.
That is, the present invention relates to the formula (I):

Wherein X ¹ and X ² are each a hydrogen atom, halogen, alkoxy, alkylthio, hydroxy or cyano; Y is alkyl; n is 1 to 10; G ¹ and G ² are each a hydrogen atom, Q, -C (= B) Q , -C (= B) DQ, -C (= B) N (L) Q, -SQ, -SO 2 Q, -SN (L) Q, -SN (L) C (= B) DQ or —SO ₂ N (L) Q; L is a hydrogen atom, alkyl, haloalkyl, phenylalkyl, alkenyl, haloalkenyl, phenylalkenyl, alkynyl, haloalkynyl or phenylalkynyl; A, B and D are each an oxygen atom or a sulfur atom; Q is an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted ring Hydrocarbon group or acid A difluoroalkanamide-based compound represented by a 5- to 12-membered heterocyclic group containing an arbitrary heteroatom selected from an atom, a sulfur atom and a nitrogen atom (the heterocyclic group may be substituted) The present invention also relates to a salt thereof, a production method thereof, and a pest control agent containing the same.

  A pest control agent comprising a novel difluoroalkanamide compound of the formula (I) as an active ingredient has an extremely high control effect against pests at a low dosage, and is a natural enemy or mammal of crops, pests. Combined safety for animals.

Alkyl which may be substituted represented by Q, cycloalkyl which may be substituted, alkenyl which may be substituted, alkynyl which may be substituted, cyclic hydrocarbon group which may be substituted or oxygen atom, sulfur atom And a 5- to 12-membered heterocyclic group (which may be substituted) containing any heteroatom selected from nitrogen atom and substituted with halogen, nitro, cyano or K An optionally substituted alkyl, a cycloalkyl optionally substituted with K, an alkenyl optionally substituted with K, an alkynyl optionally substituted with K, a cyclic hydrocarbon group optionally substituted with M ¹ , an oxygen atom, 5- to 12-membered heterocyclic group containing an arbitrary hetero atom selected from a sulfur atom and a nitrogen atom (the heterocyclic group may be substituted with M ¹ ), —OR ¹ , —SR ¹ , —NR ¹ R ² , —COR ¹ , —CO ₂ R ¹ , —COSR ¹ , —CSOR ¹ , —CS ₂ R ¹ , —SO ₂ NR ¹ R ² , —CONR ¹ R ² , —CSNR ¹ R ² , —C ^{(= NOV) R 1, -N} (R 1) COR 3, -N (R 1) CO 2 R 3, -N (R 1) COSR 3, -N (R 1) CSOR 3, -N (R 1 ^{_{) CS 2 R 3, -N (}} R 1) SO 2 R 3, -SOR 3, -SO 2 R 3, -CSR 3, -OCOR 3, -OCSR 3, -SCOR 3, -SCSR 3, trialkylsilyl , Trialkylsilyloxy and the like, and the number of substitutions may be 1 or 2 or more, and in the case of 2 or more, they may be the same or different.

The K, halogen, nitro, cyano, optionally substituted cyclic hydrocarbon group M ^1, an oxygen atom, 5- to 12-membered heterocyclic ring, optionally containing heteroatoms selected from sulfur atom and a nitrogen atom group (the heterocyclic group may be substituted by ^{M 1), - OM 2,} -SM 2, -NM 2 M 3, -COM 2, -CO 2 M 2, -COSM 2, -CSOM 2, - _{^{CS 2 M 2, -SO 2 NM}} 2 M 3, -CONM 2 M 3, -CSNM 2 M 3, -C (= NOV) M 2, -N (M 2) COM 4, -N (M 2) CO _{^{2 M 4, -N (M 2}} ) COSM 4, -N (M 2) CSOM 4, -N (M 2) CS 2 M 4, -N (M 2) SO 2 M 4, -SOM 4, -SO _{^{2 M 4, -CSM 4, -OCOM}} 4, -OCSM 4, -SCOM 4, a -SCSM ⁴ And the like. The number of substitution of K may be 1 or 2 or more, and in the case of 2 or more, they may be the same or different.

M ¹ is halogen, nitro, cyano, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, —OR ⁴ , —SR ⁴ , —NR ⁴ R ⁵ , —COR ⁴ , _{^{-CO 2 R 4, -COSR 4,}} -CSOR 4, -CS 2 R 4, -SO 2 NR 4 R 5, -CONR 4 R 5, -CSNR 4 R 5, -C (= NOV) R 4, - ^{N (R 4) COR 6,} -N (R 4) CO 2 R 6, -N (R 4) COSR 6, -N (R 4) CSOR 6, -N (R 4) CS 2 R 6, -N (R ⁴ ) SO ₂ R ⁶ , —SOR ⁶ , —SO ₂ R ⁶ , —CSR ⁶ , —OCOR ⁶ , —OCSR ⁶ , —SCOR ⁶ , —SCSR ^{6 and the} like can be mentioned. The number of substitution of M ¹ may be 1 or 2 or more, and in the case of 2 or more, they may be the same or different.

The M ² and M ^3, each represents a hydrogen atom, alkyl which may be substituted by M ^5, cycloalkyl which may be substituted by M ^5, alkenyl which may be substituted with M ^5, which may be substituted by M ⁵ A good alkynyl, a cyclic hydrocarbon group optionally substituted with M ¹ , a 5- to 12-membered heterocyclic group containing any heteroatom selected from an oxygen atom, a sulfur atom and a nitrogen atom (the heterocyclic group is M ^And may be substituted with ¹ ). M ¹ is as described above.
The M ^4, alkyl which may be substituted by M ^5, M cycloalkyl which may be substituted with ^5, M ⁵ alkenyl which may be substituted with, which may be alkynyl substituted by M ^5, substituted by M ¹ A 5- to 12-membered heterocyclic group containing any heteroatom selected from a cyclic hydrocarbon group, an oxygen atom, a sulfur atom and a nitrogen atom (which may be substituted with M ¹⁾ Good). M ¹ is as described above.

The M ^5, halogen, which may be alkoxy substituted by M ^1, M alkylthio optionally substituted with ^1, alkyl sulfates be substituted by M ¹ alkylsulfinyl, optionally substituted by M ^{1 alkylsulfonyl,} -M ^6, -OM ^6, and the like -SM ^6. The number of substitution of M ⁵ may be 1 or 2 or more, and when it is 2 or more, they may be the same or different. M ¹ is as described above.
M ⁶ is a cyclic hydrocarbon group which may be substituted with M ¹ , a 5- to 12-membered heterocyclic group containing any hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom (heterocyclic group) May be substituted with M ¹ ). M ¹ is as described above.

The R ¹ and R ^2, each a hydrogen atom, alkyl which may be substituted by M ^7, cycloalkyl which may be substituted by M ^7, alkenyl which may be substituted with M ^7, which may be substituted by M ⁷ A good alkynyl, a cyclic hydrocarbon group optionally substituted with M ¹ , a 5- to 12-membered heterocyclic group containing any heteroatom selected from an oxygen atom, a sulfur atom and a nitrogen atom (the heterocyclic group is M ^And may be substituted with ¹ ). M ¹ is as described above.
The R ^3, alkyl which may be substituted by M ^7, cycloalkyl which may be substituted by M ^7, alkenyl which may be substituted with M ^7, which may be substituted by M ⁷ alkynyl, substituted by M ¹ A 5- to 12-membered heterocyclic group containing any heteroatom selected from a cyclic hydrocarbon group, an oxygen atom, a sulfur atom and a nitrogen atom (which may be substituted with M ¹⁾ Good). M ¹ is as described above.

M ⁷ is a halogen, a cyclic hydrocarbon group which may be substituted with M ¹ , a 5- to 12-membered heterocyclic group containing any hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom (hetero ring radical may be substituted by ^{M 1), - OM 8,} -SM 8, -NM 8 M 9, -COM 8, -CO 2 M 8, -COSM 8, -CSOM 8, -CS 2 M _{^{8, -SO 2 NM 8 M 9}} , -CONM 8 M 9, -CSNM 8 M 9, -C (= NOV) M 8, -N (M 8) COM 10, -N (M 8) CO 2 M 10 ^{, -N (M 8) COSM 10} , -N (M 8) CSOM 10, -N (M 8) CS 2 M 10, -N (M 8) SO 2 M 10, -SOM 10, -SO 2 M 10 , -CSM ¹⁰ , -OCOM ¹⁰ , -OCSM ¹⁰ , -SCOM ¹⁰ , -SCSM ^{10 and the} like. The number of substitution of M ⁷ may be 1 or 2 or more, and when it is 2 or more, they may be the same or different. M ¹ is as described above.

The M ⁸ and M ^9, each a hydrogen atom, alkyl which may be substituted by M ^1, cycloalkyl which may be substituted by M ^1, alkenyl which may be substituted by M ^1, be substituted by M ¹ A good alkynyl, a cyclic hydrocarbon group optionally substituted with M ¹ , a 5- to 12-membered heterocyclic group containing any heteroatom selected from an oxygen atom, a sulfur atom and a nitrogen atom (the heterocyclic group is M ^And may be substituted with ¹ ). M ¹ is as described above.
The M ^10, alkyl which may be substituted by M ^1, cycloalkyl which may be substituted by M ^1, alkenyl which may be substituted by M ^1, which may be substituted by M ¹ alkynyl, substituted by M ¹ A 5- to 12-membered heterocyclic group containing any heteroatom selected from a cyclic hydrocarbon group, an oxygen atom, a sulfur atom and a nitrogen atom (which may be substituted with M ¹⁾ Good). M ¹ is as described above.

As of V, hydrogen atom, alkyl which may be substituted by M ^1, cycloalkyl which may be substituted by M ^1, which may be alkenyl substituted by M ^1, which may be alkynyl substituted by M ^1, M ¹ A 5- to 12-membered heterocyclic group containing any heteroatom selected from a cyclic hydrocarbon group, an oxygen atom, a sulfur atom and a nitrogen atom which may be substituted with (the heterocyclic group is substituted with M ¹⁾ May be included). M ¹ is as described above.

Examples of R ⁴ and R ⁵ include a hydrogen atom, alkyl, haloalkyl, arylalkyl, heteroarylalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl, heteroaryl and the like.
R ⁶ includes alkyl, haloalkyl, arylalkyl, heteroarylalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl, heteroaryl and the like.
Examples of halogen or halogen as a substituent include fluorine, chlorine, bromine or 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 or alkyl moiety may be linear or branched, and specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl And C _1-12 such as dodecyl.
The alkenyl or alkenyl moiety may be linear or branched, and specific examples thereof are vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3-butadienyl, 1-hexenyl, 1-heptenyl. , 4-octenyl, 2-decenyl, C _2-12 such as 2-dodecenyl, and the like.
The alkynyl or alkynyl moiety may be either linear or branched, and specific examples thereof include ethynyl, 2-butynyl, 2-pentynyl, 3-hexynyl, 4,4-dimethyl-2-pentynyl, 4-octynyl, Examples include C _2-12 such as 2-decynyl and 2-dodecynyl.

  The cyclic hydrocarbon group may be monocyclic or condensed polycyclic, and may be saturated or may have an unsaturated moiety. Specific examples of the monocyclic hydrocarbon group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclooctenyl, cyclohexadienyl, cyclooctadienyl, cyclooctynyl, phenyl and the like. Specific examples of the condensed polycyclic hydrocarbon group include naphthyl, anthryl, phenanthryl, indenyl, indanyl and the like.

  Examples of the 5- to 12-membered heterocyclic group containing an arbitrary hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom include a monocyclic or condensed polycyclic group containing 1 to 4 hetero atoms. Of the heterocyclic group. The heterocyclic group may be saturated or may have an unsaturated moiety, the methylene moiety may be converted to oxo or thioxo, and an N-oxide such as N-oxypyridyl. It may be. Preferred examples include 1) thienyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl, triazolyl, tetrazolyl, dithiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, thiazinyl, Pyranyl, benzothienyl, benzofuranyl, indolyl, isoindolyl, benzothiazolyl, benzoisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, indazolyl, cyclopentapyrazolyl, benzothiadiazolyl, benzotriazolyl, quinolyl, isoquinolyl , Phthalazinyl, cinnolinyl, quinazolinyl, quinoxalinyl, benzotriazinyl, na Heterocyclic groups selected from the group consisting of thylidinyl, thiazolopyridyl, benzodioxolyl, benzodioxinyl, pyrazolopyrimidinyl, triazolopyrimidinyl, purinyl, etc. 2) Some of these heterocyclic groups were hydrogenated Partially saturated heterocyclic group, 3) saturated heterocyclic group in which these heterocyclic groups are completely hydrogenated, or 4) dithiazolyl, oxazinyl, thiazinyl, pyranyl, cyclopentapyrazolyl, benzodioxolyl, partially saturated heterocyclic ring And an oxo or thioxo heterocyclic group in which a methylene moiety in the group or saturated heterocyclic group is converted to oxo or thioxo.

  Although some combinations may exist in the above-mentioned heterocyclic group depending on the position of the hetero atom or the difference in the condensation site, these are all included in the present invention. For example, thiadiazolyl includes 1,2,3-thiadiazolyl, 1,3,4-thiadiazolyl, triazolyl includes 1,2,3-triazolyl, 1,2,4-triazolyl, and triazinyl includes 1 , 2,4-triazinyl, 1,3,5-triazinyl, benzothienyl includes benzo [b] thienyl, benzo [c] thienyl, benzofuranyl includes benzo [b] furanyl, benzo [c] Furanyl is included, benzoisothiazolyl includes 1,2-benzisothiazolyl, 2,1-benzisothiazolyl, and benzisoxazolyl includes 1,2-benzisoxazolyl, 2 1,1-benzisoxazolyl, and benzothiadiazolyl includes 1,2,3-benzothiadiazolyl and 2,1,3-benzothiadiazolyl. The same applies to a partially saturated heterocyclic group, a saturated heterocyclic group, or an oxo or thioxo heterocyclic group.

The partially saturated heterocyclic group described above is one in which a part of the heterocyclic group is hydrogenated. For example, 4,5-dihydrothiazolyl, 4,5-dihydrooxazolyl, 4,5-dihydroisoxazolyl, 4,5-dihydro-1H-imidazolyl, 4,5-dihydro-1H-pyrazolyl, 3,4,5,6-tetrahydropyridinyl, 1,4,5,6-tetrahydropyrimidinyl, 2,3-dihydrobenzofuranyl, 4a, 5,6,7,8,8a-hexahydroquinoxalinyl Etc.
Examples of the saturated heterocyclic group include those in which the heterocyclic group is completely hydrogenated. For example, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl and the like can be mentioned.

  The aforementioned oxo or thiooxo heterocyclic group is a dithiazolyl, oxazinyl, thiazinyl, pyranyl, cyclopentapyrazolyl, benzodioxolyl, partially saturated heterocyclic group or a methylene moiety in a saturated heterocyclic group converted to oxo or thioxo. Etc. For example, 2-oxotetrahydrothienyl, 2-thioxotetrahydrothienyl, 2-oxotetrahydrofuranyl, 2-thioxotetrahydrofuranyl, 2-oxopyrrolidinyl, 2,5-dioxopyrrolidinyl, 2,4-di Oxothiazolidinyl, 4-oxo-4,5-dihydrooxazolyl, 4-oxo-4,5-dihydro-1H-imidazol-2-yl, 5-oxo-4,5-dihydro-1H-pyrazolyl 3-oxo-2,3-dihydro-1H-pyrazolyl, 5-thioxo-5H- [1,2,4] dithiazolyl, 6-oxo-1,6-dihydropyridinyl, 6-oxo-1,6 -Dihydropyridazinyl, 2,6-dioxo-1,2,3,6-tetrahydropyrimidinyl, 3-oxo-3H- [1,2,4] triazinyl, 2-oxo-1,2-dihydroquinoli Le, such as 1,3-dioxo-1,3-dihydroisoindol-2-yl.

Cycloalkyl or cycloalkyl moieties include those of C _3-8 such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like.
Aryl or aryl moieties include phenyl, naphthyl, anthryl, phenanthryl, indenyl, indanyl and the like.
Examples of the heteroaryl or heteroaryl moiety include those similar to the above heterocyclic group.

  Examples of the salt of the difluoroalkanamide compound of the formula (I) include any agriculturally acceptable salt. Examples thereof include alkali metal salts such as sodium salt and potassium salt; magnesium salt and calcium. Alkaline earth metal salts such as salts; ammonium salts such as dimethylamine salts and triethylamine salts; inorganic acid salts such as hydrochlorides, perchlorates, sulfates and nitrates; such as acetates and methanesulfonates Organic acid salts and the like.

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

In the reaction [A], X ¹ , X ² , Y, n, A, G ¹ and G ² are as described above. Examples of the salt of the compound of formula (III) include a salt with an organic acid or an inorganic acid, such as hydrochloride, sulfate, oxalate, methanesulfonate, and the like.

Reaction [A] can be performed in the presence of a base, if necessary. Examples of the base include trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, N, N-dimethylaniline, N, N-diethylaniline, N-ethyl-N-methylaniline, 1,8-diazabicyclo [5.4.0] -7-undecene, 1,4-diazabicyclo [2.2.2] octane and the like. Tertiary amines; alkali metals such as sodium and potassium; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; sodium hydride and potassium hydride Alkali metal hydrides such as sodium bicarbonate,
One kind or two or more kinds can be appropriately selected from alkali metal bicarbonates such as potassium bicarbonate; alkyllithiums such as butyllithium. The base can be used in an amount of 1 to 5 moles, preferably 1 to 2.5 moles based on the compound of the formula (II).

  Reaction [A] can be performed in presence of a solvent as needed. The solvent may be any solvent that is inert to the reaction. For example, aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; aromatics such as benzene, toluene, xylene and pyridine. Hydrocarbons; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, and trichloroethane; ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and anisole; Esters such as methyl acetate, ethyl acetate, propyl acetate; ketones such as acetone, diethyl ketone, methyl ethyl ketone, methyl isobutyl ketone; acetonitrile, propionitrile, N, N-dimethylformamide One or two or more kinds of polar aprotic solvents such as dimethylsulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, and N-methylpyrrolidone can be appropriately selected.

The reaction [A] can be carried out in an inert gas atmosphere if necessary. Examples of the inert gas include gases such as nitrogen, helium, and argon.
The reaction [A] can be carried out usually at −78 to + 250 ° C., preferably −78 to + 150 ° C., and the reaction time is usually about 0.1 to 72 hours, preferably about 0.1 to 24 hours. .

In the reaction [B], X ¹ , X ² , Y, n, A, G ¹ and G ² are as described above, and T is an oxygen atom or a sulfur atom. Moreover, as a salt of the compound represented by Formula (III), the thing similar to what was illustrated by said reaction [A], etc. are mentioned.
Reaction [B] can be azeotropically dehydrated in the presence of a solvent or can be carried out in the presence of a condensing agent.
The solvent used in the azeotropic dehydration may be any solvent as long as it is inert to the reaction. For example, one or two or more kinds can be appropriately selected from those exemplified in the reaction [A]. . In addition, when the reaction is performed in the presence of a condensing agent, a solvent may be used as necessary. However, the solvent used here may be any solvent as long as it is inert to the reaction. 1 type (s) or 2 or more types can be selected as appropriate from those exemplified in [A].

Examples of the condensing agent used in the reaction [B] include carbodiimides such as 1,3-dicyclohexylcarbodiimide, 1,3-diisopropylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride; And phosphoric acid dichloride phenyl ester, diethyl phosphorocyanidate, 1,3,5-triaza-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride, cyanuric chloride, Isobutyl chloroformate, chlorosulfonyl isocyanate, N, N′-carbonyldiimidazole,
Examples thereof include trifluoroacetic anhydride. The condensing agent can be used in an amount of 1 to 5 mol, desirably 1 to 2 mol per mol of the compound of formula (IV).

  Reaction [B] can be performed in presence of a base as needed. Examples of the base include trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, N, N-dimethylaniline, One or more kinds can be appropriately selected from tertiary amines such as N, N-diethylaniline and N-ethyl-N-methylaniline. The base can be used in an amount of 0.1 to 5 moles, preferably 0.1 to 2.5 moles relative to the compound of formula (IV).

The reaction [B] can be carried out in an inert gas atmosphere if necessary. Examples of the inert gas include nitrogen, helium, and argon.
The reaction [B] can be carried out usually at −78 to + 250 ° C., preferably 0 to 150 ° C., and the reaction time is usually about 0.1 to 72 hours, preferably about 0.1 to 24 hours.

In the reaction [C], X ¹ , X ² , Y, n, A, G ¹ , G ² and T are as described above, and Z is C _1-4 alkyl. Moreover, as a salt of the compound represented by Formula (III), the thing similar to what was illustrated by said reaction [A], etc. are mentioned.
Reaction [C] can be carried out in the presence of a base, if necessary. One or more bases can be appropriately selected from those exemplified in the above reaction [A] and alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium butoxide. The base can be used in an amount of 0.01 to 5 times mol, preferably 0.01 to 2.5 times mol, of the compound of formula (V).

Reaction [C] can be performed in presence of a solvent as needed. The solvent may be any solvent as long as it is inert to the reaction. For example, one or two or more solvents can be appropriately selected from those exemplified in the above reaction [A].
The reaction [C] can be carried out in an inert gas atmosphere if necessary. Examples of the inert gas include gases such as nitrogen, helium, and argon.
The reaction [C] can be carried out usually at −78 to + 250 ° C., preferably 0 to 150 ° C., and the reaction time is usually about 0.1 to 72 hours, preferably about 0.1 to 24 hours.

In the reaction [D], X ¹ , X ² , Y, n, A and G ¹ are as described above, and G ^2a is Q, -C (= B) Q, -C (= B) DQ, -C (= B) N (L) Q, -SQ, a -SO 2 Q, -SN (L) Q, -SN (L) C (= B) DQ or _{-SO 2 N (L) Q,} X 3 Is halogen, and Q, B, D and L are as described above.
Reaction [D] can be performed in presence of a base as needed. One or more bases can be appropriately selected from those exemplified in the above reaction [A]. The base can be used in an amount of 0.01 to 10 times mol, preferably 0.01 to 5 times mol for the compound of formula (I-1).

  The reaction [D] can be carried out in the presence of N-trialkylsilyl-alkyl carbamates as necessary. N-trialkylsilyl-alkyl carbamates can be appropriately selected from one or more of N-trimethylsilyl-ethyl carbamate, N-triethylsilyl-methyl carbamate, and the like. N-trialkylsilyl-alkyl carbamates can be used in an amount of 0.01 to 10 times mol, preferably 0.01 to 5 times mol for the compound of formula (I-1).

Reaction [D] can be performed in presence of a solvent as needed. The solvent may be any solvent as long as it is inert to the reaction. For example, one or two or more solvents can be appropriately selected from those exemplified in the above reaction [A].
Reaction [D] can be performed in the atmosphere of an inert gas as needed. Examples of the inert gas include nitrogen, helium, and argon.
The reaction [D] can be carried out usually at −78 to + 250 ° C., preferably 0 to 150 ° C., and the reaction time is usually about 0.1 to 72 hours, preferably about 0.1 to 24 hours.

In the reaction [E], X ¹ , X ² , Y, n, A and G ¹ are as described above, G ^2b is alkyl, U is phenyl substituted with alkyl, haloalkyl, alkoxy, phenyl, halogen. Or phenyl substituted with alkyl.
Reaction [E] can be performed in the presence of a base, if necessary. One or more bases can be appropriately selected from those exemplified in the above reaction [A]. The base can be used in an amount of 0.01 to 10 times mol, preferably 0.01 to 5 times mol for the compound of formula (I-1).

Reaction [E] can be performed 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, one or two or more solvents can be appropriately selected from those exemplified in the above reaction [A].
The reaction [E] can be carried out under an inert gas atmosphere if necessary. Examples of the inert gas include gases such as nitrogen, helium, and argon.
The reaction [E] can be carried out usually at −78 to + 250 ° C., preferably 0 to 150 ° C., and the reaction time is usually about 0.1 to 72 hours, preferably about 0.1 to 24 hours.

In the reaction [F], X ¹ , X ² , Y, n, G ¹ and G ² are as described above.
Examples of the thioning agent used in the reaction [F] include phosphorus pentasulfide and Lawesson's reagent. The thioning agent can be used in an amount of 1 to 10 times mol, preferably 1 to 4 times mol for the compound of formula (I-2).

  Reaction [F] can be performed in presence of a solvent as needed. The solvent may be any solvent that is inert to the reaction. For example, aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; aromatics such as benzene, toluene, xylene and pyridine. Hydrocarbons; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, and trichloroethane; ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and anisole; Esters such as methyl acetate, ethyl acetate, and propyl acetate; one or more polar aprotic solvents such as acetonitrile, propionitrile, dimethyl sulfoxide, and sulfolane can be appropriately selected.

The reaction [F] can be carried out in an inert gas atmosphere if necessary. Examples of the inert gas include gases such as nitrogen, helium, and argon.
The reaction [F] can be carried out usually at −78 to + 250 ° C., preferably 0 to 150 ° C., and the reaction time is usually about 0.1 to 72 hours, preferably about 0.1 to 24 hours.

In the reaction [G], X ¹ , X ² , Y, n, A, G ¹ and G ² are as described above.
Reaction [G] can be performed in presence of a solvent as needed. The solvent may be any solvent inert to the reaction, for example, aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; aromatic hydrocarbons such as pyridine; chlorobenzene, Halogenated hydrocarbons such as dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, and trichloroethane; ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and anisole; methyl acetate, ethyl acetate, One type or two or more types can be appropriately selected from esters such as propyl acetate; polar aprotic solvents such as acetonitrile, propionitrile, dimethyl sulfoxide, and sulfolane.

Reaction [G] can be performed in the atmosphere of an inert gas as needed. Examples of the inert gas include gases such as nitrogen, helium, and argon.
The reaction [G] can usually be carried out at −78 to + 250 ° C., preferably −78 to 150 ° C., and the reaction time is usually about 0.1 to 72 hours, preferably about 0.1 to 24 hours. .

In the reaction [H], X ² , Y, n, A, G ¹ and G ² are as described above, and R is alkyl.
Reaction [H] can be performed in presence of a solvent as needed. The solvent may be any solvent inert to the reaction, for example, aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; aromatic hydrocarbons such as pyridine; chlorobenzene, Halogenated hydrocarbons such as dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, and trichloroethane; ethers such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and anisole; methyl acetate, ethyl acetate, One type or two or more types can be appropriately selected from esters such as propyl acetate; polar aprotic solvents such as acetonitrile, propionitrile, dimethyl sulfoxide, and sulfolane.

The reaction [H] can be carried out in an inert gas atmosphere if necessary. Examples of the inert gas include gases such as nitrogen, helium, and argon.
The reaction [H] can be carried out usually at −78 to + 250 ° C., preferably −78 to 150 ° C., and the reaction time is usually about 0.1 to 72 hours, preferably about 0.1 to 24 hours. .

Each starting material of formula (II), formula (IV) or formula (V) in the reactions [A] to [C] and formula (VIII) in the reaction [G] or [H] is (1) It is a known compound, (2) it can be produced according to the synthesis examples described later or in accordance with it, or (3) it is produced by the method described in WO92 / 15555, EP661289 or EP432861, or a method according to them. Can do.
The above (3) will be described more specifically. A) The method described on page 15 line 16 to page 16 line 3 of WO 92/15555, a method of appropriately performing normal chlorination or esterification subsequently, Synthesis Example 16, 22, 28 or 42 of the same publication Or a method according to them. B) The method described in EP 661289, page 13, line 25 to page 14, line 37, the method described in Synthesis Example Z1, Z2 or Z3 of the same, or a method according to them. C) The method described in EP 432861, page 4, line 22 to page 8, line 45, the method described in Synthesis Example 3, 4, 8, 9, 10, 16, 20 or 21 of the same publication, or Similar method.

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

  Pesticides for agricultural and horticultural use are useful as, for example, insecticides, acaricides, nematicides, and soil-killing insecticides. Plant parasitic mites such as rustic mites, mites, aphids such as peach aphids, cotton aphids, diamondback moths, weevil, scallops, codling moths, ball worms, tobacco worms, mai moths, staghorn moths, prickly beetles, 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, mosquito moths, bark beetles; It is effective for control of clothes such as clothes, house pests, and indoor dust mites such as Scarlet mite, Scarlet mite, Scarlet 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, as an active ingredient compound (generic name; including some pending applications) of insecticide, acaricide, nematicide or soil insecticide, that is, pest control agent, for example, Profenofos (Profenofos) ), Dichlorvos, Fenamiphos, Fenitrothion, EPN, Diazinon, Chlorpyrifos-methyl, Acephate, Prothiofos, Phosthiazate, phosphocarb ), Cadusafos, Disulfoton, Chlorpyrifos, Demeton-S-methyl, Dimethoate, Methhamidophos, Parathion, AKD-3088 [( 2-Cyanoimino-3-ethylimidazolidin-1-yl) -O-ethyl-S-propyl-phosphonothi Organic phosphate compounds such as Oate]; Carbaryl, Propoxur, Aldicarb, Carbofuran, Thiodicarb, Methomyl, Oxamyl, Ethiofencarb ), Pirimicarb, Fenobucarb, Carbosulfan, Carbamate compounds such as Benfuracarb; Nereistoxins such as Cartap, Thiocyclam, Bensultap Derivatives; Organochlorine compounds such as Dicofol, Tetradifon, Endosulfan; Organometallic compounds such as Fenbutatin Oxide; Fenvalerate, Permethrin, Si Permethrin, deltametry Pyrethroid compounds such as Deltamethrin, Cyhalothrin, Tefluthrin, Ethofenprox, Fenpropathrin, Bifenthrin; Diflubenzuron, Chlorfluazuron Benzoylurea compounds such as Chlorfluazuron, Teflubenzuron, Flufenoxuron, Lufenuron, Novaluron, Bistrifluron, Noviflumuron; Methoprene Juvenile hormone-like compounds such as Pyriproxyfen and Fenoxycarb; pyridazinone compounds such as Pyridaben; Fenpyroximate, Fipronil, Tebufenpyrad, Etipro Pyrazole compounds such as Ethiprole, Tolfenpyrad, Acetoprole, Pyrafluprole, Pyriprole; Imidacloprid, Nitenpyram, Atenamiprid, Acetamiprid, Neonicotinoids such as Thiacloprid, Thiamethoxam, Clothianidin, Dinotefuran; Tebufenozide, Methoxyfenozide, Chromafenozide, Halofenozide Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazone compounds, and other compounds include flonicamid (Flonicamid), buprofezin (Huprofezin), hexithiazox (Hexythiazox) Amitraz, Chlordimeform, Silafluofen, Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr, Indoxacarb, Equinol ), Cyromazine, 1,3-dichloropropene, Diafenthiuron, Benclothiaz, Flufenerim, Pyridalyl, Spirodiclofen , Bifenazate, spiromesifen, propargite, clofentezine, etoxazole, fluacrypyrim, metaflumizone, flubendiamide (Flubendiam) ide), compounds such as cyflumetofen, amideflumet, and the like. Furthermore, microbial agents such as BT agents, entomopathogenic virus agents, entomopathogenic fungi agents, nematode pathogenic fungi agents, avermectin, emamectin-benzoate, milbemectin, spinosad ( Spinosad), Ivermectin, Lepimectin, and other antibiotics, Azadirachtin, and natural products such as rotenone can be used in combination.

  In the above-mentioned other agricultural chemicals, as an active ingredient compound of a fungicide (generic name; including partial application, or Japan Plant Protection Association test code), for example, mepanipyrim, pyrimethanil, cyprodinil Pyridinamine compounds such as Cyprodinil; pyridinamine compounds such as Fluazinam; triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, Penconazole (Penconazole), Flucilazole (Flusilazole), Microbutanil (Myclobutanil), Cyproconazole (Terbuconazole), Hexaconazole (Hexaconazole), Farconazole-cis (Furconazole-cis), Prochloraz ( Prochloraz), Metco Metconazole, Epoxyconazole, Tetraconazole, Oxpoconazole sulfate, Sipconazole, Prothioconazole, Triadimenol, Full Azolic compounds such as Flutriafol, Difenoconazole, Fluquinconazole, Fenbuconazole, Bromuconazole, Diniconazole; Quinomethionate Quinoxaline compounds; dithiocarbamate compounds such as Maneb, Zineb, Mancozeb, Polycarbamate, Metiram, Propineb; Fthalide Organochlorine compounds such as Chlorothalonil and Quintozene; imidazole compounds such as Benomyl, Thiophanate-Methyl, Carbendazim and Cyazofamid; Cymoxanil Cyanoacetamide compounds such as: Metalaxyl, Metalaxyl M, Oxadixyl, Offurace, Benalaxyl, Furalaxyl, Cyprofuram Compound; sulfenic acid type compound such as Dichlofluanid; copper type compound such as cuprichydroxide and organic copper (Oxine Copper); isoxazole type compound such as hymexazol; Organophosphorus compounds such as luminium (Fosetyl-Al), Turkish phosmethyl (Tolcofos-Methyl), S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate N-halogenoalkyl compounds such as Captan, Captafol and Folpet; dicarboximide compounds such as Procymidone, Iprodione and Vinclozolin; Benzanilide compounds such as Flutolanil, Mepronil, Zoxamid, Tiadinil; Piperazine compounds such as Triforine; Pyridine compounds such as Pyrifenox; Carbinol compounds such as Fenarimol and Flutriafol; Piperidine compounds such as Fenpropidine; Morpholine compounds such as Fenpropimorph; Fentine hydroxide (Fentin Hydroxide), organotin compounds such as Fentin Acetate; urea compounds such as Pencycuron; dimethomorphs, cinnamic acid compounds such as Flumorph; dietofencarb ( Phenylcarbamate compounds such as Diethofencarb; Cyanopyrrole compounds such as Fludioxonil and Fenpiclonil; Azoxystrobin, Kresoxim-Methyl, Metominophen (Metomi) nofen), Trifloxystrobin, Picoxystrobin, Oryzastrobin, Dimoxystrobin, Fluoxastrobin, Fluacrypyrin and other strobilurins Compounds; oxazolidinone compounds such as Famoxadone; thiazole carboxamide compounds such as Ethaboxam; silylamide compounds such as Silthiopham; Iprovalicarb, Benthiavalicarb Amino acid amide carbamate compounds such as; imidazolidine compounds such as Fenamidone; hydroxyanilide compounds such as Fenhexamid; benzenesulfonamide-based compounds such as famid); oxime ether-based compounds such as Cyflufenamid; phenoxyamide-based compounds such as Fenoxanil; triazole-based compounds such as Simeconazole; polyoxins And other compounds such as Isoprothiolane, Tricyclazole, Pyroquilon, Diclomezine, Probenazole, Quinoxyfen, Propamocarb Hydrochloride , Spiroxamine, Chloropicrin, Dazomet, Carbam sodium salt (Metam-sodium), Nicobifen, Metrafenone, MTF-753 (Pen) Opirado, Pentiopyrad), UBF-307, diclocymet (Diclocymet), and the like Purokin'ajido (Proquinazid).

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

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

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

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

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

  Other ectoparasites include, for example, lice such as bovine lice, foal lice, sheep lice, bovine white lice, head lice; lice such as dog lice; blood-sucking dipterous pests such as bovine abs, quail sharks, . In addition, examples of endoparasites include nematodes such as lungworms, benthic worms, tuberous worms, gastric parasites, roundworms, and filamentous worms; tapeworms; flukes; coccidium, malaria parasites, and intestinal granulocysts Protozoa such as Toxoplasma and Cryptosporidium.

  Examples of host animals include pets such as dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (eg, pigeons, parrots, nine-birds, wild birds, parakeets, juvenile pine, canary); Domestic animals such as pigs and sheep; poultry such as 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, it is particularly effective for dogs and cats. Among domestic animals, it is particularly effective for cows and 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.

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

Next, some are illustrated as desirable embodiments of the compound of the present invention. However, the present invention is not limited to these.
(1) The compound of the above formula (I), wherein X ¹ and X ² are both bromine atoms.
(2) The compound of the above formula (I), wherein A is an oxygen atom.
(3) The compound of the above formula (I), wherein G ¹ is Q.
(4) The compound of the above formula (I), wherein G ¹ is —C (═B) Q.
(5) The compound of the above formula (I), wherein G ² is a hydrogen atom.
(6) The compound of the above formula (I), wherein B is an oxygen atom.
(7) The above formula (I) wherein Q is a 5- to 12-membered heterocyclic group containing any heteroatom selected from an oxygen atom, a sulfur atom and a nitrogen atom (the heterocyclic group may be substituted) ).

(8) The compound of the above formula (I), wherein Q is a cyclic hydrocarbon group which may be substituted with W. Here, W is halogen, nitro, cyano, alkyl optionally substituted with K, alkenyl optionally substituted with K, alkynyl optionally substituted with K, or cyclic hydrocarbon optionally substituted with M ¹ A 5- to 12-membered heterocyclic group containing an arbitrary heteroatom selected from a group, an oxygen atom, a sulfur atom and a nitrogen atom (the heterocyclic group may be substituted with M ¹ ), —OR ¹ , — ^{SR 1, -NR 1 R 2,} -COR 1, -CO 2 R 1, -COSR 1, -CSOR 1, -CS 2 R 1, -SO 2 NR 1 R 2, -CONR 1 R 2, -CSNR 1 ^{R 2, -C (= NOV)} R 1, -N (R 1) COR 3, -N (R 1) CO 2 R 3, -N (R 1) COSR 3, -N (R 1) CSOR 3, _{^{-N (R 1) CS 2 R}} 3, -N (R 1) SO 2 R 3, -SOR 3 _{^{, -SO 2 R 3, -CSR 3}} , -OCOR 3, -OCSR 3, -SCOR 3, -SCSR 3, trialkylsilyl or trialkylsilyloxy. K, M ¹ , R ¹ , R ² , R ³ and V are as described above. The number of substitution of W may be 1 or 2 or more, and when it is 2 or more, they may be the same or different.
(9) A compound in which X ¹ , X ² , A, B, G ¹ , G ² and Q in (1) to (8) above are appropriately combined.

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-pyridyl) -7-bromo-7- (bromodifluoromethyl) nonanoic acid amide (compound No. 64 described later)
0.7 g of N- (2-pyridyl) 7-ethyl-8,8-difluoro-7-octenamide is dissolved in 15 ml of dry diethyl ether, and a mixture of 260 μl of bromine and 5 ml of dichloromethane is added dropwise at 0 ° C. in a nitrogen atmosphere. did. After completion of the dropwise addition, the mixture was refluxed for 4 hours, poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and ethyl acetate was removed under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 9/1) to obtain 0.937 g of the oily desired product.

Synthesis example 2
Synthesis of N- (2-pyridyl) 7-bromo-7- [difluoro (methoxy) methyl] nonanoic acid amide (compound No. 261 described later)
2.5 g of N- (2-pyridyl) 7-ethyl-8,8-difluoro-7-octenoic acid amide was dissolved in 50 ml of methanol, and a mixture of 930 μl of bromine and 20 ml of dichloromethane was added dropwise. After completion of the dropwise addition, the mixture was refluxed for 1 hour, poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and ethyl acetate was removed under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 9/1 to 8/2) to obtain 0.261 g of the oily desired product.

Synthesis example 3
Synthesis of N- (7-bromo-7- (bromodifluoromethyl) nonanoyl) 2-methylbenzamide (Compound No. 184 described later) N- (7-ethyl-8,8-difluoro-7-octenoyl) 2-methylbenzamide 0.3 g was dissolved in 7 ml of dry diethyl ether, and a mixture of 57 μl of bromine and 2 ml of dichloromethane was added dropwise at 0 ° C. in a nitrogen atmosphere. After stirring at the same temperature for 30 minutes, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and ethyl acetate was removed under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 8.5 / 1.5-8 / 2) to obtain 0.136 g of the desired product having a melting point of 65-72.5 ° C.

Next, typical examples of the compounds of the present invention represented by the formula (I) are listed in Tables 1 to 3, and their NMR spectrum data are listed in Table 4. These compounds can be synthesized based on the above-described synthesis examples or various production methods of the compound of the present invention described above. In Tables 1 to 3, No. represents Compound No. In Tables 1 to 3, Me is a methyl group, Et is an ethyl group, n-Pr is a normal propyl group, i-Pr is an isopropyl group, t-Bu is a tertiary butyl group, c-Pr represents a cyclopropyl group, c-Bu represents a cyclobutyl group, and Ph represents a phenyl group. In Tables 1 to 3, Ph (2-Cl) is a phenyl group substituted with a chlorine atom at the 2-position, and is Ph (4-Ph (4-CF ₃ )). Represents a phenyl group substituted with a phenyl group at the 4-position (with a CF ₃ group substituted at the 4-position of the phenyl group), and other similar descriptions are also based thereon.

Next, test examples are described.
Test Example 1 Nile spider mite insecticide test A chemical solution was prepared so that the concentration of the compound of the present invention was 50 ppm. Only one primary bean leaf was left and transplanted to a pot (diameter: 8 cm, height: 7 cm), and 20 adult 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 were considered dead. When the insecticidal rate was calculated | required about the said compound No. 51, 53, 64, 65, 184, and 261, all the compounds showed the high control effect of 80% or more.
Insecticidal rate (%) = (Number of dead insects / number of worms) × 100

Test Example 2 Medicinal effect test for Phytophthora tick 1 ml (concentration: 10 μmg / ml) of an acetone solution of the compound of the present invention is dropped on a 9 cm petri dish inner surface with a micropipette. After the petri dish inner surface is dried, 60 to 180 young 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 3 Medicinal Efficacy Test Using Dogs Against Phytophthora Tick 50 young mites of Phytophthora ticks are released into the ears of dogs (beagle, 8 months old) and artificially infested. 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 4 Drug efficacy test using a dog against a cat flea 100 books of a cat flea non-blood-sucking adult within 3 days after emergence were released on the back coat of a dog (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 check 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) 72 parts by weight of clay (3) Sodium lignin sulfonate 8 parts by weight or more is uniformly mixed to obtain a wettable powder.
Formulation Example 2
(1) Compound of the present invention 5 parts by weight (2) Talc 95 parts by weight or more is 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 alkylphenyl ether 10 parts by weight (4) Xylene 50 parts by weight or more are uniformly mixed and dissolved To make an emulsion.

Formulation Example 4
(1) Clay 68 parts by weight (2) Lignin sulfonic acid soda 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) Fine powder silica A mixture of each component of 25 parts by weight or more and the compound of the present invention 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) Oxidated polyalkylphenyl phosphate-triethanolamine 2 parts by weight (3) Silicone 0.2 parts by weight (4) Water 47.8 parts by weight or more uniform (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are added to the stock solution mixed and pulverized, and mixed uniformly, granulated, and dried to obtain a granulated wettable powder.
Formulation Example 6
(1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octyl phenyl ether 1 part by weight (3) Polyoxyethylene phosphate ester 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1)- (3) is mixed uniformly 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-methyl-2-pyrrolidone 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) Oxidated polyalkylphenyl phosphate-triethanolamine 2 parts by weight (3) Silicone 0.2 part by weight (4) Xanthan gum 0.1 part by weight (5) Ethylene glycol 5 parts by weight (6) Water 52.7 parts by weight 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) Diethylene glycol monoethyl ether 90 parts by weight or more of components are mixed uniformly to obtain a solution.

Claims (6)

Formula (I):

Wherein X ¹ and X ² are each a hydrogen atom, halogen, alkoxy, alkylthio, hydroxy or cyano; Y is alkyl; n is 1 to 10; G ¹ and G ² are each a hydrogen atom, Q, -C (= B) Q , -C (= B) DQ, -C (= B) N (L) Q, -SQ, -SO 2 Q, -SN (L) Q, -SN (L) C (= B) DQ or —SO ₂ N (L) Q; L is a hydrogen atom, alkyl, haloalkyl, phenylalkyl, alkenyl, haloalkenyl, phenylalkenyl, alkynyl, haloalkynyl or phenylalkynyl; A, B and D are each an oxygen atom or a sulfur atom; Q is an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted ring Hydrocarbon group or acid A difluoroalkanamide-based compound represented by a 5- to 12-membered heterocyclic group containing an arbitrary heteroatom selected from an atom, a sulfur atom and a nitrogen atom (the heterocyclic group may be substituted) Or a salt thereof. Formula (I):

Wherein X ¹ and X ² are each a hydrogen atom, halogen, alkoxy, alkylthio, hydroxy or cyano; Y is alkyl; n is 1 to 10; G ¹ and G ² are each a hydrogen atom, Q, -C (= B) Q , -C (= B) DQ, -C (= B) N (L) Q, -SQ, -SO 2 Q, -SN (L) Q, -SN (L) C (= B) DQ or —SO ₂ N (L) Q; L is a hydrogen atom, alkyl, haloalkyl, phenylalkyl, alkenyl, haloalkenyl, phenylalkenyl, alkynyl, haloalkynyl or phenylalkynyl; A, B and D are each an oxygen atom or a sulfur atom; Q is an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted ring Hydrocarbon group or acid A difluoroalkanamide-based compound represented by a 5- to 12-membered heterocyclic group containing an arbitrary heteroatom selected from an atom, a sulfur atom and a nitrogen atom (the heterocyclic group may be substituted) Or a method of producing a salt thereof,
(1) Formula (II):

(Wherein, X ¹ , X ² , Y, n and A are as described above), and the formula (III):

(Wherein, G ¹ and G ² are as described above) or a salt thereof, or (2) Formula (IV):

(Wherein, X ¹ , X ² , Y, n and A are as defined above, and T is an oxygen atom or a sulfur atom), and a formula (III):

(Wherein, G ¹ and G ² are as described above) or a salt thereof, or (3) Formula (V):

Wherein X ¹ , X ² , Y, n, A and T are as described above, and Z is C _1-4 alkyl, and the formula (III):

(Wherein, G ¹ and G ² are as described above) or a salt thereof, or (4) Formula (I-1):

(Wherein, X ¹ , X ² , Y, n, A and G ¹ are as described above) and the formula (VI):

(In the formula, G ^2a is Q, -C (= B) Q, -C (= B) DQ, -C (= B) N (L) Q, -SQ, -SO ₂ Q, -SN (L) Q, -SN (L) C (= B) DQ or -SO ₂ N (L) Q, X ³ is halogen, and Q, B, D and L are as described above. React with compound or (5) Formula (I-1):

(Wherein X ¹ , X ² , Y, n, A and G ¹ are as described above) and formula (VII):

^Wherein G ^2b is alkyl and U is alkyl, haloalkyl, alkoxy, phenyl, phenyl substituted with halogen or phenyl substituted with alkyl, or (6) Formula (I-2):

(Wherein X ¹ , X ² , Y, n, G ¹ and G ² are as described above) or a thionation agent, or (7) Formula (VIII) :

(Wherein Y, n, A, G ¹ and G ² are as described above) and formula (IX):

(Wherein, X ¹ and X ² are as defined above) or (8) Formula (VIII):

(Wherein Y, n, A, G ¹ and G ² are as described above), a compound represented by formula (X):

(Wherein X ² is as described above) and formula (XI):

(Wherein R is alkyl), and a compound represented by the following reaction. A pest control agent comprising the difluoroalkanamide compound or salt thereof according to claim 1 as an active ingredient. An agricultural and horticultural pest control agent comprising the difluoroalkanamide compound or a salt thereof according to claim 1 as an active ingredient. An insecticide, acaricide or nematicide containing the difluoroalkanamide compound or salt thereof of claim 1 as an active ingredient. A method for controlling pests by applying an effective amount of the difluoroalkanamide compound or a salt thereof according to claim 1.