WO2006118267A1 - Anthranylamide compound, process for producing the same and pest control agent containing the compound - Google Patents

Abstract

For years, a vast variety of pest control agents have been employed, which to no small extent have problems, such as poor efficacy. Thus, there is a demand on the development of pest control agents relieved in such problems. There are provided anthranylamide compounds of the formula: (I) wherein R1 is a halogen or an alkyl; R2 is hydrogen, a halogen, an alkyl, etc.; each of R3, R4 and R5 is hydrogen, a halogen, an alkyl, etc.; R6 is a halogen, an alkyl or a haloalkyl; A is hydrogen, an alkyl, an alkylthioalkyl, a haloalkylthioalkyl, an alkylsulfinylalkyl, a haloalkylsulfinylalkyl, an alkylsulfonylalkyl, a haloalkylsulfonylalkyl, or a substitutable C3-C4 cycloalkyl-alkyl; and X is CR7 or nitrogen.

Description

 Specification

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

 Technical field

 [0001] WO03Z24222 and WO01Z70671 (Patent Documents 1 and 2) each disclose an anthramide compound having a certain chemical structure. However, it has an alkyl substituted with C cycloalkyl as a substituent corresponding to A in the following formula (I).

 3-4

 No compound is described anywhere. WO04Z67528 (Patent Document 3) discloses a compound in which the acyl group bonded to the amino moiety of the anthranylamide is a pyrazole carbonyl group, and the nitrogen substituent of the amide moiety is cyclopropylmethyl. On the other hand, in the compound of the present invention, the substituent bonded to anthralamide is pyrrole, and the chemical structures of the two are different.

[0002] Patent Document 1: International Publication WO03Z24222

 Patent Document 2: International Publication WO01Z70671

 Patent Document 3: International Publication WO04Z67528

 Disclosure of the invention

 Problems to be solved by the invention

[0003] A number of pest control agents have been used for many years, but many have various problems such as insufficient efficacy, pests gaining resistance and limiting their use. Therefore, it is desired to develop a new pest control agent with few disadvantages, for example, a pest control agent capable of controlling various pests that are problematic in the field of agriculture and horticulture, and pests parasitic on animals.

 Means for solving the problem

 [0004] The present inventors have made various studies on anthranilamide compounds in order to find better pest control agents. As a result, the present inventors have found that a novel anthra-amide compound has an extremely high control effect against pests at a low dose, and completed the present invention.

[0005] That is, the present invention provides a compound of formula (I): [0006] [Chemical 1]

(Wherein R ¹ is halogen or alkyl, R ² is a hydrogen atom, halogen, alkyl, haloalkyl, cyano or methoxycarbon, and each of R ³ , R ⁴ and R ⁵ is Halogen; alkyl; haloalkyl; alkoxy; haloalkoxy; formyl; alkoxyalkyloxymethyl; cycloalkylcarbonyl; haloalkylcarbonyl; substituted with alkoxy, alkylamino or dialkylamino, or iminoalkyl; or An alkyl substituted with 1 or 2 cyanos; R ⁶ is a halogen, alkyl or haloalkyl; A is a hydrogen atom; alkyl; alkylthioalkyl; haloalkylthioalkyl; alkylsulfinylalkyl; haloalkylsulfinylalkyl; Sulfonylalkyl Haloalkylsulfonyl alkyl; or halogen, O be substituted with at least one substituent selected group force consisting completion alkyl and haloalkyl, C cycloalkyl - alkyl, X is CR ⁷ or nitrogen atom, R ⁷ is water

 3-4

Element A, halogen, alkyl or haloalkyl, provided that (1) when A is a hydrogen atom, alkyl, alkylthioalkyl, alkylsulfinylalkyl or alkylsulfonylalkyl, any of R ³ , R ⁴ or R ⁵ 1 One is formyl; alkoxyalkyloxymethyl; cycloalkylcarbonyl; haloalkylcarbonyl; iminoalkyl optionally substituted with alkoxy, alkylamino or dialkylamino; or an alkyl substituted with 1 or 2 cyanos; ) When R ³ and R ⁵ are hydrogen atoms and R ^{4 is} halogen, haloalkyl or haloalkoxy, A is not haloalkylthioalkyl, haloalkylsulfuralkyl or haloalkylsulfoalkyl. Anthra-amide compounds, N-oxide or a salt thereof, a production method thereof, a pest control agent containing the same, and the like. The invention's effect

 [0008] A pest control agent comprising the novel anthranilamido compound of formula (I) as an active ingredient is

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

 BEST MODE FOR CARRYING OUT THE INVENTION

R⁶、 R⁷又は A中のハロゲン又は置換基としてのハロゲンとして は、フッ素、塩素、臭素又はヨウ素の各原子が挙げられる。置換基としてのハロゲンの 数は 1又は 2以上であってよぐ 2以上の場合、各ハロゲンは同一でも相異なってもよ い。また、ハロゲンの置換位置はいずれの位置でもよい。[0009]

Examples of the halogen in R ⁶ , R ⁷ or A or the halogen as a substituent include each atom of fluorine, chlorine, bromine or iodine. The number of halogens as substituents is 1 or 2 or more. When 2 or more, each halogen may be the same or different. Further, the halogen substitution position may be any position.

R⁶、 R⁷又は A中のアルキル又はアルキル部分としては、メチ ル、ェチル、プロピル、イソプロピル、ブチル、 tert-ブチル、ペンチル、へキシルのよう な、直鎖又は分枝状の C のアルキルが挙げられる。

Alkyl or alkyl moieties in R ⁶ , R ⁷ or A include linear or branched C alkyl such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl. Can be mentioned.

 1-6

Examples of the cycloalkyl part of the cycloalkyl carbonyl of R ³ , R ⁴ or R ⁵ include C alkyl such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

 3-6

 I can get lost.

Examples of R ³ , IT or R ⁵ alkalis include linear or branched C alkalis such as bur, aryl, 1-probe and iso-probe.

 2-6

 The cycloalkyl part of C cycloalkyl-alkyl of A includes cyclopropyl

3-4

 Or cyclobutyl is mentioned. Of these, cyclopropyl is desirable.

 Halogen, alkyl or haloalkyl which is a C cycloalkyl-alkyl substituent of A

3-4

 The number of substitutions of alkyl is 1 or 2 or more. When it is 2 or more, each substituent may be the same or different. In addition, the substitution position of each substituent may be a shift position. A C

 3-4 Chloalkyl-alkyl is preferably unsubstituted or has 1 to 5 substituents if it has the above-mentioned substituents.

[0010] The salt of the anthracamide compound of the formula (I) includes any salt that is agriculturally acceptable. For example, alkali metal salts such as sodium salt and potassium salt; alkaline earth metal salts such as magnesium salt and calcium salt; ammonium salt such as dimethyl ammonium salt and triethyl ammonium salt; hydrochloride salt Inorganic salts such as perchlorate, sulfate, nitrate; organic acid salts such as acetate, methanesulfonate, etc. It is done.

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

 [0012] The anthracamide compound of the formula (I), its N-oxide or a salt thereof (hereinafter abbreviated as the present invention compound) is prepared by the following reactions [A] to [B] and production of ordinary salts: It can be manufactured according to the method.

 [0013] [Chemical 2]

(I) The reaction [A] can usually be carried out in the presence of a base when Z is a chlorine atom. Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydride, water Alkali metal hydrides such as potassium iodide; trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylviridine, 4 pyrrolidinopyridine, N-methyl Tertiary amines such as morpholine, Ν, Ν dimethylaniline, Ν, Ν jetylaniline, Νethyl-Ν-methylaniline, 1,8 diazabicyclo [5.4.0] 7undecene, 1,4-diazabicyclo [2.2.2] octane One type or two or more types can be appropriately selected from the class. The base can be used in an amount of 1 to 5 times mol, preferably 1 to 2.5 times mol, of the compound of formula (II).

 The reaction [Α] can be carried out in the presence of a solvent if desired when Ζ is a chlorine atom. Any solvent may be used as long as it is inert to the reaction. For example, etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; halogenated compounds such as black benzene, dichlorobenzene, dichloromethane, chlorophenol, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene Hydrocarbons; aromatic hydrocarbons such as benzene, toluene, xylene; acetonitryl, propio-tolyl, Ν, ジ メ チ ル dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, Ν —Polar aprotic solvents such as methylpyrrolidone; esters such as methyl acetate, ethyl acetate, propyl acetate; acetone, jetyl ketone, methyl ethyl ketone, methyl isobutyl ketone, etc. It can be appropriately selected one or more from such tons class.

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

 Reaction [A] can usually be carried out in the presence of a dehydrating condensing agent and a solvent when Z is —OH.

Dehydrating condensation agents include carbodiimides such as Ν, Ν'-dicyclohexylcarbodiimide, 1,3 diisopropylcarbodiimide, 1-ethyl 3- (3 dimethylaminopropyl) carbodiimide hydrochloride; 1,1, -carbohydrate -Rubis 1H-imidazole, phosphoric acid diester ester phosphate, Jetylphosphorus Russia-Dart 1,3,5 Triaza 2,4,6-Triphospholine 2,2,4,4,6,6 Hexachloride, cyanuric Chloride, isobuty chloroformate Chlorosulfuryl isocyanate, trifluoroacetic anhydride and the like. Any solvent may be used as long as it is inert to the reaction. For example, etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; halogenated compounds such as black benzene, dichlorobenzene, dichloromethane, chlorophenol, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene Hydrocarbons; aromatic hydrocarbons such as benzene, toluene, xylene; acetonitryl, propio-tolyl, Ν, ジ メ チ ル dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, Ν —Polar aprotic solvents such as methylpyrrolidone; esters such as methyl acetate, ethyl acetate, propyl acetate; acetone, jetyl ketone, methyl ethyl ketone, methyl isobutyl ketone, etc. Ton class; pentane, hexane, heptane, octane, can be appropriately selected one or more kinds of such aliphatic hydrocarbons such as cyclohexane.

 The reaction [Α] can usually be carried out at 20 to 60 ° C, preferably 0 to 30 ° C, when Ζ is ΟΗ. The reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours.

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

 1-4

be able to.

 Bases include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; trimethylamine, triethylamine and triisopropyl. Amines, Diisopropylethylamine, Pyridine, 4-Dimethylaminopyridine, 2,6 Dimethylviridine, 4-Pyrrolidinopyridine, N-methylmorpholine, Ν, Ν Dimethylaniline, Ν, Ν Jetylaniline, Ν Ethanolet レ ー -Metinorealine One or two or more tertiary amines such as 1,8 diazabicyclo [5.4.0] 17 undecene and 1,4 diazabicyclo [2.2.2] octane can be appropriately selected. The base can be used in an amount of 1 to 5 times mol, preferably 1 to 2.5 times mol, of the compound of formula (II).

Any solvent may be used as long as it is inert to the reaction. For example, diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxy ester Ethers such as tan; aromatic hydrocarbons such as benzene, toluene and xylene; acetonitrile, propio-tolyl, Ν, Ν-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethyla One or more polar aprotic solvents such as cetamide and メ チ ル -methylpyrrolidone; alcohols such as methanol, ethanol, propanol, normal butanol, and tert-butanol can be appropriately selected.

 Reaction [A] is usually 0 to 120 ° C, preferably 20 to 80 when Z is C alkoxy.

 1-4

 Can be performed at ° C. The reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours.

 [0017] Each of the compounds of formula (II) or formula (III) is a known compound, or can be prepared according to known materials. For example, the compound of formula (II) can be prepared according to the method described in Synthesis, 1980, page 505 or a modification thereof, and the compound of formula (III) is described in schemes 9-22 in WO 03Z24222 Can be produced according to the method described above.

 [0018] [Chemical 3]

[0019] 反応〔B〕は、通常、溶媒の存在下で行うことができる。

[0019] The reaction [B] can usually be carried out in the presence of a solvent.

 Any solvent may be used as long as it is inert to the reaction. For example, etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; halogenated compounds such as black benzene, dichlorobenzene, dichloromethane, chlorophenol, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene Hydrocarbons; aromatic hydrocarbons such as benzene, toluene, xylene; acetonitryl, propio-tolyl, Ν, Ν-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, One or more kinds can be appropriately selected from polar aprotic solvents such as メ チ ル -methylpyrrolidone. The reaction can be carried out usually at 0 to 120 ° C, preferably 20 to 80 ° C. The reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours.

 [0020] The compound of the formula (IV) can be produced according to a known compound or a known document. For example, the compound of the formula (IV) can be prepared by the method described in Org. Prep. Proceed. Int., 1993, 25, 585, the method described in schemes 8 to 10 in WO03Z24222 or the like. Can be manufactured.

In addition, among the compounds of the formula (III), the compound (Ilia) in which any one of R ³ , R ⁴ or R ⁵ is a halogen, X is a nitrogen atom, and Z is —OH. It can be produced by the following reaction [C] (wherein J is a halogen).

[0022] [Chemical 4]

 (IX) (ma) In the step 1-1 of the reaction [C], the compound (VII) is obtained by converting pyrrole and a 2-chloropyridine derivative (VI), for example, when J is a chlorine atom, Usually, it can manufacture by making it react in presence of a base. Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene, toluene, and xylene, acetonitrile, propio-tolyl, Ν, Ν-dimethylformamide, dimethylsulfoxide, and hexamethylphosphoric triamide. Polar aprotic solvents and mixtures thereof. As the base used in the reaction, for example, one or more kinds of alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydrides such as sodium hydride and potassium hydride, and the like are appropriately used. You can choose. The base can be used in an amount of 1 to 2 moles, preferably 1 to 1.2 moles per mole of pyrrole.

 The reaction temperature in step 1-1 of reaction [C] is usually 20 to 100 ° C, preferably 40 to 70 ° C. The reaction time is usually about 2 to 12 hours, preferably about 3 to 6 hours. After completion of the reaction, the compound (VII) can be isolated, for example, by performing a post-treatment operation by the following method (1) or (2).

 (1) A method in which the reaction mixture is extracted with an organic solvent, and the organic layer is dried and concentrated.

 (2) A method in which the reaction mixture is filtered and concentrated.

Further, the isolated compound (VII) can be further purified by operations such as chromatography and recrystallization. It can be refined.

 [0024] In step 12 of reaction [C], compound (VIII) is produced by carrying out a Vilsmeier reaction with respect to compound (VII) and introducing a formyl group at the 2-position of pyrrole. This comes out.

[0025] In step 1-3 of reaction [C], compound (IX) can be produced by reacting compound (VIII) with a halogenating agent. In this reaction, when an equimolar amount of the compound (VIII) is used as the halogenating agent, a compound in which any one of R ³ , R ⁴ or R ⁵ is halogen is obtained. On the other hand, when the halogenating agent is used in an amount twice or more the amount of Compound (VIII), a compound in which any two of R ³ , R ^{4 and} R ⁵ are halogens is formed.

 Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, acetonitrile, propio-tolyl, Ν, ジ メ チ ル dimethylformamide, dimethyl sulfoxide, and hexamethylphosphoric triamide. Polar aprotic solvents such as and mixtures thereof. In the step 1-3 of reaction [C], examples of the halogenating agent used in the reaction include N-nitrocarboxylic acid amides such as N-chlorosuccinimide, N-bromosuccinimide, and N-dosuccinimide. The reaction temperature in step 1-3 of reaction [C] is usually 0 to 100 ° C, preferably 30 to 70 ° C. The reaction time is usually about 2 to 48 hours, preferably about 3 to 12 hours.

 [0026] In step 1-4 of reaction [C], compound (Ilia) can be produced by reacting compound (IX) with an oxidizing agent. The reaction is usually performed in the presence of water and an organic solvent. Examples of the solvent used in the step 1-4 of the reaction [C] include ethers such as tetrahydrofuran, ethyleneglycolinoresmethinoleatenore, tert-butinoremethinoleatenore; alcohols such as tert-butanol Polar aprotic solvents such as acetonitrile, propio-tolyl, Ν, Ν-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, and mixtures thereof.

Further, examples of the oxidizing agent used in step 1-4 of the reaction [C] include metal oxidizing agents such as chromic anhydride and potassium permanganate, and halohalates such as sodium chlorite. When halite salts are used as oxidizing agents, Do not use halogen scavengers such as chilly 2-butene! In some cases, the halo of 5-position of pyrrole occurs simultaneously with the acid of aldehyde to carboxylic acid. The reaction temperature is usually 0 to 80 ° C, preferably 20 to 40 ° C. The reaction time is usually about 10 to 96 hours.

 In addition, among the compounds of the formula (III), a compound (II lb) in which X is a nitrogen atom and Z is —OH can be produced by the following reaction [D] (wherein , J is a halogen).

 [0028] [Chemical 5]

 (1Mb)

 (XIII)

[0029] The compound of substituted pyrrole (X), which is a starting material for reaction [D], is described in Journal of Fluorine Chemistry, 1991, 53, 61, and Chemische Berichte, 122, 169. It is known. Steps 2-1, 2-2, 2-3, and 2-4 of Reaction [D] are the same as the corresponding Steps 1-1, 1-2, 1-3, and 1-4 of Reaction [C], respectively. It can be carried out under reaction conditions.

[0030] Among the compounds (III), compound (IIIc) in which X is CR ⁷ and Z is -OH can be produced by the following reaction [E].

[0031] [Chemical 6] [E]

 (XVII) (lllc)

[0032] In step 3-1 of reaction [E], compound (XV) is produced by reacting an aline derivative (XIV) with 2,5 dimethoxytetrahydrofuran usually in the presence of a solvent. Can do. Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene, toluene and xylene; alcohols such as methanol and ethanol; organic acids such as acetic acid and propionic acid; acetonitrile, propio-tolyl, Ν, Ν— And polar aprotic solvents such as dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, and mixtures thereof. 2,5-Dimethoxytetrahydrofuran can be usually used in an amount of 1.5 to 2 moles compared to the phosline derivative (XIV). The reaction temperature is usually 20 to 150 ° C, preferably 70 to 100 ° C. The reaction time is usually about 2 to 12 hours, preferably about 3 to 6 hours.

 [0033] In step 3-2 of reaction [E], compound (XVI) is reacted by using compound (XV) in place of compound (VII) in the same manner as in step 12 of reaction [C]. Can be manufactured.

 [0034] In step 3-3 of reaction [E], compound (XVII) is reacted in the same manner as in step 13 of reaction [C] using compound (XVI) instead of compound (VIII). Can be manufactured.

[0035] In step 3-4 of reaction [E], compound (IIIc) is prepared in the same manner as in step 1-4 of reaction [C], except that compound (XVII) is used instead of compound (IX). Produced by reacting It can be done.

[0036] Further, among the compounds of the formula (III), R ³ may be substituted with formyl or alkoxy !, iminoalkyl, alkylamino, or may be substituted with dialkylamino, iminoalkyl or The compound (Illd), which is an alkenyl substituted with 1 or 2 cyano groups, X is a nitrogen atom, and Z is —OH, can be produced by the following reaction [F] (wherein Hal is a halogen, and each of R and R ⁸ is a hydrogen atom or C alkyl).

 1-6

 [0037] [Chemical 7]

 (Hid)

[0038] In step 41 of reaction [F], compound (XVIII) is reacted in the same manner as in step 13 of reaction [C] using compound (VII) instead of compound (VIII). Can be manufactured.

[0039] In step 4-2 of reaction [F], when R ⁸ is a hydrogen atom, compound (XIX) is replaced with compound (VII) in the same manner as in step 12 of reaction [C]. It can be produced by reacting with compound (XVIII). And when R ⁸ is C alkyl,

 1-6

Compound (XVIII) is mixed with an appropriate acid chloride or acid anhydride under the Friede Crafts reaction conditions. It can be produced from a kit that can be reacted with a salt.

 [0040] In step 43 of the reaction [F], the compound (XX) is obtained by converting the compound (XIX) into a tertiary amine as a scavenger for carbon monoxide, alcohol as a nucleophile and acid generated in the system. In the presence of an alkoxy carbonyl group using a transition metal catalyst such as palladium or cobalt and a phosphine ligand. As the alcohol to be used, methanol, which includes methanol, ethanol, propanol and the like, is desirable. The tertiary amines used are trimethylamine, triethylamine, triisopropylamine, diisopropylpropylamine, pyridine, 4 dimethylaminopyridine, 2,6 dimethylviridine, 4-pyrrolidinopyridine, N-methylmorpholine, Ν,ジ メ チ ル Dimethylaniline, Ν, ジ ェ Jetyl-Arine, チ ル -Ethyl Ν-Methyl-Arine, 1,8 Diazabicyclo [5.4.0] 1-7 Decene, 1,4 Diazabicyclo [2.2.2] Octane . Examples of the solvent used in the reaction include polar aprotic solvents such as Ν, ジ メ チ ル dimethylformamide, dimethyl sulfoxide, and Ν-methylpyrrolidone. As the catalyst system used for the reaction, a combination of palladium acetate and diphenylphosphinopropane is desirable. The reaction is usually carried out at 25 to 120 ° C, preferably 50 to 70 ° C. The reaction time is usually about 1 to 24 hours, preferably about 3 to 7 hours.

 The compound of the formula (XX) can be produced according to known literature. For example, the compound (XX) can be produced according to the method described in Tetrahedron Letters, 1992, page 33, pages 1959-1962, or the like.

[0041] In step 4-4 of reaction [F], when R ³ is an iminoalkyl group optionally substituted with alkoxy, it can be produced by the following reaction [G] (wherein R and R ⁸ Each is a hydrogen atom or C alkyl, R ⁹ is C alkyl, and J is halogen)

[0042] [Chemical 8]

 (XXIII)

[0043] The compound (XXII) can be produced by reacting the compound (XX) with a 0-alkylhydroxylamine mineral salt in the presence of a base group, usually using a solvent. Examples of the base include one or more of alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal acetates such as sodium acetate; tertiary amines such as trimethylamine and triethylamine. Can be appropriately selected. The base can be used in an amount of 1 to 4 moles, preferably 1.1 to 2.2 moles to the compound (XX). As the solvent, any solvent inert to the reaction may be used. For example, ethers such as jetyl ether, butinoreethinoreethenole, tetrahydrofuran, dixanthane, dimethoxyethane; Halogenated hydrocarbons such as mouth benzene, dichlorobenzene, dichloromethane, black mouth form, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; aromatic hydrocarbons such as benzene, toluene, xylene; methanol, ethanol One or more alcohols can be appropriately selected from such alcohols. The reaction temperature is usually 25 to 120 ° C, preferably 50 to 80 ° C. The reaction time is usually about 1 to 12 hours, preferably about 3 to 7 hours.

[0044] In step 4-4 of reaction [F], when R ³ is an iminoalkyl group which may be substituted with alkylamino or dialkylamino, it can be produced by the following reaction: Each of R and R ⁸ is a hydrogen atom or C alkyl, and R ⁹ is C alkyl.

1-6 1-6 and R ^1Q is a hydrogen atom or C alkyl). [0045] [Chemical 9]

[0046] Compound (XXIV) is the above compound (XX) and alkyl hydrazine! / Can be produced by reacting N, N dialkylhydrazine in a solvent, usually in the presence of an acid catalyst. . Examples of the acid catalyst to be used include inorganic acids such as hydrochloric acid and sulfuric acid; organic acids such as acetic acid and p-toluenesulfonic acid. As the solvent, any solvent inert to the reaction may be used. For example, ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; aromatic hydrocarbons such as benzene, toluene and xylene; alcohols such as methanol and ethanol One type or two or more types can be appropriately selected. The reaction temperature is usually 10 to 120 ° C, preferably 50 to 80 ° C. The reaction time is usually about 30 minutes to 8 hours, preferably about 1 to 4 hours.

[0047] In step 44 of reaction [F], when R ³ is an alkenyl group substituted with one cyano group, it can be produced by the following reaction [I] (wherein R And each of R ⁸ is a hydrogen atom or C alkyl).

 1-6

[0048] [Chemical 10]

 (XXVII) Compound (XXVI) is the compound (XX), phospho-um salt (Ph P + CH CNCf) and base

 3 2

Or Wittig reaction with alkyl, or alkyl phosphite ((EtO) P (= 0) CH CN) and

This can be produced by carrying out the Horner-Wadsworth-Emmons reaction using a 2 base in an ordinary solvent. Bases used include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydride and potassium hydride and the like. Alkali metal hydrides: trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6 dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, Ν, Ν Tertiary amines such as dimethylaniline, Ν, Ν jetylaniline, Νethyl Ν-methylaniline, 1,8 diazabicyclo [5.4.0] 7 undecene, 1,4-diazabicyclo [2.2.2] octane; η-butyllithium One or more kinds of alkyllithiums can be appropriately selected. Any solvent may be used as long as it is inert to the reaction. For example, ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane and dimethoxyethane; benzene, toluene, Aromatic hydrocarbons such as xylene; 1 or 2 from halogenated hydrocarbons such as black benzene, dichlorobenzene, dichloromethane, black mouth form, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene, etc. More than one species can be selected as appropriate. The reaction temperature is usually −10 to 100 ° C., desirably 20 to 50 ° C. The reaction time is Usually, it is about 1 to 36 hours, preferably about 5 to 12 hours.

[0050] In step 44 of reaction [F], when R ³ is an alkenyl group substituted with two cyano groups, it can be prepared by the following reaction CF] (wherein R and R Each of R ⁸ is a hydrogen atom or C alkyl).

 1-6

 [0051] [Chemical 11]

 (XXIX)

[0052] Compound (XXVIII) can be produced by reacting the compound (XX) and malononitrile with a solvent in the presence of a base. Bases used include piperidine, trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6 dimethylviridine, 4 pyrrolidinopyridine, Ν— Organic bases such as methyl morpholine, Ν, ジ メ チ ル dimethylaniline, Ν, チ ル cetylaniline, Ν ethyl ー -methylaline; ammonium acetate, acetic acid salts such as sodium acetate; sodium methoxide, It can be appropriately selected from sodium alkoxides such as sodium ethoxide. Any solvent may be used as long as it is inert to the reaction. For example, ethers such as jetinoreethenore, butinoreethinoreatenore, tetrahydrofuran, dioxane, dimethoxyethane; benzene; 1 type or 2 or more types can be suitably selected from aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol and propanol; carboxylic acids such as formic acid and acetic acid. The reaction temperature is usually −10 to 100 ° C., desirably 20 to 50 ° C. Reaction time is usually 1 The time is about 36 hours, preferably about 5-12 hours.

 [0053] In step 45 of reaction [F] (or steps 45a to 45d of reaction [G] to i), compound (Hid) is obtained by mixing compound (XXI) in an ordinary solvent. It can be produced by hydrolysis using potassium trimethylsilanolate. Any solvent may be used as long as it is inert to the reaction. For example, ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, and dimethoxyethane; benzene, toluene In addition, one or more aromatic hydrocarbons such as xylene can be appropriately selected. The reaction temperature is usually 10 to 80 ° C, preferably 20 to 40 ° C. The reaction time is usually about 3 to 48 hours, preferably about 8 to 15 hours.

 [0054] Desirable embodiments of the pest control agent containing the compound of the present invention will be described below. The pest control agent containing the compound of the present invention includes, for example, various pest control agents that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural pest control agents, and pest control agents parasitic on animals, that is, animals. It is particularly useful as a parasite control agent.

[0055] Pesticides for agricultural and horticultural use include, for example, power useful as insecticides, acaricides, nematicides, and soil-killing insecticides. Specifically, Namihada, -Senamihada, Kanzahadada, Mikanhada Plant parasites such as apple hada, chinodokorida, mandarin orange, mite, etc .; koga, weevil, lotus root, codling moth, ball worm, tobacco bad worm, maiiga, kono noiga, chinokokakumon hamaki, apple kokukakumon amaki , Momoshin Taiga, Nashihime Shinchii, Tamanayaga, Power Braga, Colorado potato beetle, Urihamushi, Ballui bilville, Aphids, Pruners, leafhoppers, scale insects, stink bugs, whiteflies, thrips, beetles, beetles Such as moss, ants, and clams Agricultural insect pests; plant parasitic nematodes such as root-knot sentin, cyst-scented, Nesare sentinu, rice singale-scented, strawberry sentinu, pine-nosed sentry, etc .; slugs, maimai, etc. Stomach pests such as gastropods, isopods such as bark beetles, staghorns, etc .; Sanitary pests such as house dust mites, house flies, mosquito power, cockroaches, etc .; Bataga, Azuki beetle, Kokunosutomodoki, Goomushimodashi Stored pests such as moss; clothing, house pests such as Iga, Himekatsubushimushi, termites, etc .; It is effective for controlling ticks. Among them, the agricultural and horticultural pest control agent containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. In addition, the agricultural and horticultural 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, and wire can be obtained by treating the soil with an agricultural and horticultural pesticide containing the compound of the present invention. At the same time as controlling insects, gastropods, and isopoda, it can also control pests on the foliage.

 Another desirable aspect of the pest control agent containing the compound of the present invention is to comprehensively control the plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. Agricultural and 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 adjuvants. Used in various forms such as suspensions, aqueous solvents, emulsions, solutions, pastes, aerosols, and microdispersions. Needless to say, the present invention can be applied to any formulation form commonly used in the art as long as it meets the purpose of the present invention. Adjuvants used in the formulation include diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch, etc. Solid carrier: water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, black benzene, cyclohexane, dimethyl sulfoxide, Ν, Ν-dimethylformamide, dimethylacetamide, Ν— Methyl-2-pyrrolidone, alcohol and other solvents; fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkylaryl sulfates, alkyl disulfates Glycol ether sulfate , Alcohol sulfate, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignite sulfonate, alkyl diether ether disulfonate, polystyrene sulfonate, alkyl phosphate ester salt, Alkyl aryl phosphate, styryl aryl phosphate, polyoxyethylene alkyl ether sulfate Salt, polyoxyethylene alkylaryl ether sulfate, polyoxyethylene alkylaryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkylaryl phosphate, naphthalenesulfonic acid formalin condensate Anionic surfactant spreader such as salt of sorbitan; sorbitan fatty acid ester, glycerin fatty acid ester, fatty acid polydaricelide, fatty acid alcohol polydaryl alcohol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer , Polyoxyethylene alkyl ether, polyoxyethylene alkyl ether, polyoxyethylene styryl ether, polyoxyethylene glycol alkyl ether, polyester Nonionic surfactants such as lenglycol, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid ester Agents: Olive oil, Kapok oil, castor oil, palm oil, straw oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, cut oil, liquid paraffin and other vegetable and mineral oils And so on. Each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. In addition to the above-mentioned adjuvants, they can be appropriately selected from those known in the art, for example, extenders, thickeners, anti-settling agents, antifreeze agents, dispersion stabilizers, phytotoxicity reductions. Various commonly used adjuvants such as agents and fungicides can also be used. The compounding ratio of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10. In actual use of these preparations, use them as they are, or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. It can be added and used.

The application of 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, application time, application location, pest type and occurrence. However, it is generally carried out at an active ingredient concentration of 0.05 to 800,000 ppm, preferably 0.5 to 500,000 ppm, and the application amount per unit area is 0.05 to 50000 g, preferably 1 to 30000 g, of the present compound per hectare. In addition, pest control containing the compound of the present invention The application of the pest control agent for agricultural and horticultural use, which is another desirable embodiment of the pesticide, is performed according to the application of the pest control agent. The present invention also includes a method for controlling harmful organisms by such an application method, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.

 [0058] Various formulations of agricultural and horticultural pesticides containing the compounds of the present invention, or their dilutions, are usually applied by a commonly used application method, ie, spraying (eg spraying, spraying, misting, Atomizing, dusting, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.), immersion poison bait, etc. It is also possible to give livestock a mixture of the above-mentioned active ingredients in feed to inhibit the occurrence and growth of harmful insects, particularly harmful insects, in their excreta. It can also be applied by the ultra-low volume method. In this method, it is possible to contain 100% of the active ingredient.

 [0059] The pesticide for agricultural and horticultural use containing the compound of the present invention can be used in combination with or combined with other agricultural chemicals, fertilizers, safeners, etc. May show sex. Other pesticides include herbicides, insecticides, acaricides, nematicides, soil pesticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. It is done. In particular, a mixed pest control composition in which the compound of the present invention and one or more active compound compounds of other agricultural chemicals are used in combination or in combination is preferred in terms of application range, timing of chemical treatment, control activity, etc. It is possible to improve. The compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be used separately by mixing them at the time of spraying, or may be used by preparing both together. The present invention also includes such a mixed pest control composition.

The mixing ratio between the compound of the present invention and the active ingredient compound of other agricultural chemicals cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, pest type and occurrence, etc. 300 to 300: 1, preferably 1: 100 to 100: 1. The appropriate amount to be applied is 0.1 to 50000 g, preferably 1 to 30000 g as the total amount of active ingredient compounds per hectal. The present invention also includes a method for controlling pests by a method for applying such a mixed pest control composition. In the above-mentioned other agricultural chemicals, as an active ingredient compound (generic name; including some pending applications) of insecticides, acaricides, nematicides or soil insecticides, that is, pest control agents, for example, profenofos ( Profenofos, Cyclonorevos, Dichlorvos, Fenamithion, Fenitrothion, EPN, Diazinon, Chlorpyrif os-methyl, Acephate, Prothiofos, Phostiazate Fosth iazate), Phosphocarb, Phosphocarb, Cadusafos, Disulfoton, Chlorpyrifos, Demeton-S-methyl, Dimethoate, Memethamidophos (Methamidophos) Phosphate ester compounds; Power barbaryl, Propoxur, Aldicarb, Carboforan Carno carbs such as Thiodicarb, Methomyl, Oxamyl, Ethiofencarb, Pirimicarb, Fenob ucarb, Carbosulfan, Benforacarb Compounds: Nereistoxin derivatives such as Cartap, Thiocyclam and Bens ultap; Organochlorine compounds such as Dicofol and Tetradifon; Fenbutatin Oxide Organometallic compounds such as: Fenvalerate, Permethrin, Cypermethrin, Deltamethrin, Cyhalothrin, Tefluthrin, Etofenprox, Fenpropa Fenpropathrin, bifenthrin (Bife pyrethroids such as nthrin; diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenenuron, nonoronone Benzoylurea compounds such as: Methoprene, Pyriproxyfen, Fenoxycarb-like compounds; Pyridazinone compounds such as Pyridaben; Fenpyroximate, fipro-l Pyrazoprido compounds such as (Fi pronil), Tebufenpyrad, Ethiprole, Tolfenpyrad, Acetoprole, Pyrafluprole, Pyriprole; Imidacloprid), -Ten Lamb (Nitenpyram), Asetamipurido (Acetamiprid), thiacloprid (Thiacloprid), Chiametoki Neo-cotinoids such as Thiamethoxam, Clothianidin, Dinoteforan; Hydrazine compounds such as Tebufenozide, Methoxyfenozide, Chromafenozide; Di-tro compounds Organic sulfur compounds; urea compounds; triazine compounds; hydrazone compounds; other compounds include Flonicamid, Buprofezin, Hexythiazox, Amitraz, Chlorimeform (Chlordimeform), Silafluofen, Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr, Indoxacarb, Indoxacarb, Aceto ), Cyromazine, 1,3-di 1,3-dichloropropene, Diafenthiuron, Benclothiaz, Flufenerim, Pyridalyl, Spirodiclofen, Bifenazate, Spiromesifene (Spiromesifen), Propargite, Clofentezine, Fluacr ypyrim, Metaflumizone, Flubendiamide, Cyflumetofen, and the like. Furthermore, microbial pesticides such as BT agents, entomopathogenic virus agents, entomopathogenic fungi agents, nematode pathogenic fungi agents, avermectin, emamectin-benzoate, minolebemectin ( Milbemectin), Spinosad, Ivermectin, Lepimectin, and other natural products such as Azadirachtin can be mixed and used together.

In the above-mentioned other agricultural chemicals, the active ingredient compound (generic name; including some pending) or Japan Plant Protection Association test code) includes, for example, mepa-pyrim (Mepanipyrim), pyrimesaal (Pyrimethanil), pyrimidinamine compounds such as Cyprodinil; pyridinamine compounds such as Fluazinam; triadimefon, bitertanol, triflumizole, etaconazole (Eta) conazole) ゝ Propiconazole, Penconazo Monole (Penconazole), Funole Silazole (Flusilazole), Microbutanil (Myclobutanil), Cyproconazole (Cypro conazole), Ta '~~ Buconan ~~ Nore (Terouconazole) ), To = γ-Saconazo ~~ Nore (Hexaconazole), Fakonazo one Noreshisu (Furconazole- cis), prochloraz (Prochloraz), Metokonazonore (Metconazole, Eho ³ r Shikonan one Honoré (Epoxiconazole), Tetofukonaso one Honoré (Tetraconazol e), O kiss Poco Nazo Honoré sulfate (Oxpoconazole fumarate) Shipukonazonore (Sipconazo le), Prothioconazole, Triadimenol, Flutriafol, Difenoconazole, Fluquinconazole, Fenbuconazoie, Bromuconan ~~ Azole compounds such as Bromuc onazole and Diniconazole; Quinoxaline compounds such as Quinomethionate; Maneb, Zineb, Mancozeb, Polycarbamate , Metiram, Propineb Dithiocarbamate compounds; organochlorine compounds such as Fthalide, Chlorothalonil and Quintozene; Benomyl, Thiophanate-Methyl, Car bendazim (Car bendazim) ), Imidazole compounds such as Cyazofamid; Cyanoxamide compounds such as Cymoxanil; Metalaxyl, Metalaxyl M, Oxadixyl, Oforace ), Benalaxyl, Furalaxyl, Cyproforam, phenylamide compounds; Dichlorfluanid, sulfenic acid compounds; Cuprichydroxide , Copper compounds such as Oxine Copper; isoxazoles such as Hymexazol Compounds: fosetyl aluminum (Fosetyl-Al), Turkish phosmethyl (Tolcofos- Methyl), S-benzyl O, O-diisopropylphos holothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate Organic phosphorus compounds such as N-halogenoalkyl compounds such as Captan, Captafol and Folpet; Procymidone, Iprodione, Vinclozolin Dicarboximide compounds such as: Flutolanil, Mepronil, Zoxamid, benzazide compounds such as Tiadinil; such as Triforine Piperazine compounds; pyridin compounds such as Pyrifenox; Fenarimol), such as Furutoriafuoru (Flutriafol) Karubino Piperidine compounds such as Fenpropidine; morpholine compounds such as Fenpropimorph; organic compounds such as Fentin Hydroxide and Fentin Acetate Tin compounds; urea compounds such as Pencycuron; cinnamate compounds such as Dimethom orph and Flumorph; and phenol carbamate compounds such as Diethofencarb Cyanobiol compounds such as Fludioxonil and Fenpiclonil; Azoxystrobin, Kresoxim-Methyl, Metominofen, Trifloxystrobin (Trifloxystrobin), Picoxystrobin, Oriza Streptobilin compounds such as Oryzastrobin, Dimoxystrobin, Fluoxastrobin, and Fluacrypyrin; Oxazolidinone compounds such as Famoxadone; ethaboxam Thiazolecarboxamide compounds such as Ethaboxam; Silamide compounds such as Silthiopham; Aminoacid amide carbamate compounds such as Iprovalicarb and Benthiavali carb; Fenamidone Imidazolidine compounds such as Fenhexamid Hydoxyxylide compounds; benzenesulfonamide compounds such as Flusulfamid; oxime ethers such as Cyflufenamid Compounds; phenoxyamide compounds such as Fenoxanil; triazole compounds such as Simeconazole; antibiotics such as polyoxins; other compounds such as isoprothiolane and tricyclazole ( Tricyclazole, Pyroquilon, Diclomezine, Probenazole, Quinoxyfen, Propamocarb Hydrochloride, Spiroxamine Chloropicrin, Dazomet D Examples include sodium sodium (Metam-sodium), -Nobibifen (Metrafenone), MTF-753 (Pentiopyrad), UBF-307, Diclocymet, Proquinazid.

In addition, as an agrochemical that can be mixed or used together with the compound of the present invention, for example, There are active compounds of herbicides as described in Farm Chemicals Handbook (2002 edition), especially those of soil treatment type.

 [0063] Examples of the animal parasite control agent 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, intestine, lungs, It is effective for the control of endoparasites parasitic on the heart, liver, blood vessels, subcutaneous, lymphoid tissue, etc., but it is particularly effective for the control of ectoparasites.

 [0064] Examples of ectoparasites include animal parasitic mites and fleas. These types are very difficult to list, so here are some examples.

 [0065] Examples of animal parasitic mites include Boophilus microplus, Rnipicephalus sanguineus, Haemaphvsalis longicorni s, and Tematani (Haemaphvsalis flava) campanula ta, chair power (Haemaphvsalis concinna), hamatophvsalis iap onica, sinker "Haemaphvsalis ias, mite (Ixodes ovatus, tick) Ticked ticks (Ixodes persulcatus), Takasago Kiraramagii (Amblvomma testudinarium), gifted Togenamatani (Haemaphvsalis megaspinosa), Amamikakumaguji (Dermacentor r eticulatus); Trisanta-(Ornithonvssus no, Na Trisanta- (

Ornithonvssus bursa, such as: Eutrombicula wic hmanni, Leptotrombidium akamushi, Leptotrom bidium pallidum, Leptotrombidium luii, Nepto autumnalis), American claw beetle (Eutrombicula alfreddugesi), crested moths of Heelenicula mivagawai: Insid ticks (Chevletiella vasguri), Ragwort ticks (Chevletiella m rasitivorax), ev Rotifer mite (Psoroptes cuniculi), Cyprioptes bovis, Otodectes cvnotis, Hydra mite (Sarcoptes scabiei), Rotifer mite (Notoedres cati) canis ) Like There are two types of Bida. Among them, the animal parasite control agent containing the compound of the present invention is particularly effective for controlling ticks and the like.

 [0066] Examples of fleas include ectoparasite worms belonging to the order Flea (Siphonaptera), more specifically fleas belonging to the family Flea (Pulicidae), Cleaphyllus (Ceratephyllus), etc. . Examples of fleas belonging to the family Fleas include: Fleafish (CtenoceDhalides cams), Catnocephalides (Ctenocephalides felis), Humanfish (Pulex irritans), -Echidnoph aga gallinacea, Examples include animal worms (Leptopsvl la segnis), Nosopsyllus fasciatus, Monopsvll us mik, etc. Among them, animal parasite control agents containing the compounds of the present invention. Is effective for the control of fleas belonging to the family Flea, especially ini fleas and cat fleas.

 [0067] Other ectoparasites include, for example, lice such as white lice, white lice, hedge lice, white lice, white lice; white lice such as white lice; blood sucking such as Usiab, Uinu power, and Thmetgebu Diptera pests. Examples of endophytic organisms include nematodes such as lungworms, bench beetles, tuberous worms, gastric parasites, roundworms, and filamentous worms; Crustacea, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms; Japanese schistosomiasis, fluke-like fluke; kokujimu, malaria parasite, intestinal floriformus, toxoplasma Protozoa such as Cryptosporidium.

 [0068] Examples of host animals include various pet animals, livestock, poultry, and the like, and more specifically, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (for example, , Pigeons, omme, nine-birds, wild birds, parakeets, pine pine, canary, etc.), sushi, horses, butter, hidge, ducks, etc. Among these, the animal parasite control agent containing the compound of the present invention is effective for the control of pests parasitic on pet animals or livestock, particularly ectoparasites. It is especially effective for dogs, cats, ushi or horses in pets or livestock.

[0069] When the compound of the present invention is used as an animal parasite control agent, it may be used as it is. Also, powders, granules, tablets, powders, capsules, liquid agents, emulsions, aquatic compounds with appropriate adjuvants. It can also be formulated and used in various forms such as a suspension and an oily suspension. The above In addition to the dosage form, any conventional dosage form used in the art can be used as long as it is suitable for the purpose of the present invention. Examples of the adjuvant used in the preparation include anionic surfactants and nonionic surfactants exemplified as the aforementioned preparation adjuvants for agricultural and horticultural pest control agents such as cetyltrimethylammonium bromide. Cationic surfactants: water, acetone, acetonitrile, monomethylacetamide, dimethylacetamide, dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol , Benzenoreanoleconole, Ethylene glycol, Propylene glycol, Polyethylene glycol, Liquid polyoxyethylene glycol nore, Butinoresin glycol nore, Ethylene glycol nole monomethinoatenore, Ethyleneglycoleno monoethylenoatenore, Diethylene glycol Solvents such as ricinole monoethylenoate, diethylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; butylhydroxyl-sol, butyhydroxytoluene, ascorbic acid, sodium metabisulfite, Anti-oxidizing agents such as propyl gallate and sodium thiosulfate; film forming agents such as polybulurpyrrolidone, polybular alcohol, and a copolymer of buryl acetate and burpyrrolidone; the agricultural and horticultural pest control agents described above And vegetable oils and mineral oils exemplified as supplements for pharmaceutical preparations; lactose, sucrose, glucose, starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other carriers such as commercially available feed ingredients. Each component of these adjuvants can be used by appropriately selecting one or more types without departing from the object of the present invention. In addition to the above-mentioned auxiliary agents, it can be used by appropriately selecting from those known in the field, and further, selected from various auxiliary agents used in the above-mentioned agricultural and horticultural fields. You can also

 [0070] The compounding ratio of the compound of the present invention and various adjuvants is usually about 0.1: 99.9 to 90:10. In actual use of these preparations, use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. It can be used as a supplement.

[0071] Administration of the compound of the present invention to a host animal is performed orally or parenterally. Examples of oral administration methods include tablets, liquids, capsules, and drugs containing the compound of the present invention. Examples include methods of administering hearth, biscuits, minced meat, and other feeds. As a parenteral administration method, for example, the compound of the present invention is prepared in an appropriate formulation and then taken into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on

(spot-on) treatment, pour-on treatment, spraying treatment, etc .; a method of administering to the body surface;

 [0072] Although the dose of the compound of the present invention to the host animal varies depending on the administration method, administration purpose, disease symptoms, etc., it is usually O.Olmg to: L00g to the body weight lKg of the host animal, preferably 0.1 It is appropriate to administer at a rate of mg to 1 Og.

 [0073] 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.

 [0074] 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. Thus, the present invention includes a prophylactic or therapeutic agent for parasite-derived animal diseases comprising the compound of the present invention as an active ingredient, and a method for preventing or treating parasite-derived animal diseases.

 [0075] When the compound of the present invention is used as an animal parasite control agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretic agents, sedatives, anti-inflammatory agents, bactericides, and coloring agents together with adjuvants. , Fragrances, preservatives and the like can be mixed or used together. If necessary, mix with or use other animal drugs and pesticides such as anthelmintics, anti-coxime, insecticides, acaricides, fleas, nematicides, bactericides, and antibacterials. In this case, the effect may be even better. The present invention includes a mixed pest control composition in which various components as described above are mixed or used together, and a pest control method using the composition, particularly control of ectoparasites or endoparasites. A method is also included.

 Example

 [0076] Examples of the present invention will be described below, but the present invention is not limited thereto. First, synthesis examples of the compound of the present invention will be described.

[0077] Synthesis Example 1 N— [4-Chloro-2-methyl-6-[[α-methyl- (cyclopropylmethyl) [Mino] carbol] -Phenol] 4 Bromo 1— (3—Black mouth 2 Pyridyl) -Pyrolulu 2-—Carboxamide (Compound No. 2)

 [0078] (1) Sodium hydride (60% oil suspension) 2. To a suspension of 8 g and dimethylformamide 300 ml, slowly add a mixed solution of pyrrole 4.7 g and dimethylformamide 20 ml under ice-cooling. Then, the mixture was stirred at room temperature for 30 minutes. Next, a mixed solution of 8.6 g of 2,3 dichroic pyridine and 30 ml of dimethylformamide was gradually added dropwise. After completion of the dropwise addition, the mixed solution was heated to 80 ° C. and reacted for 3 hours. After completion of the reaction, the mixed solution was ice-cooled, and 500 ml of water was added little by little. After extraction three times with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n hexane Z ethyl acetate = 1/1) to obtain 1 (3 chloro-2-pyridyl) pyrrole 10.2 g (Yield 99%) was obtained as a colorless oil.

 [0079] (2) 5.4 ml of phosphorus oxychloride was gradually added dropwise to 16.9 ml of dimethylformamide under ice cooling, followed by stirring at room temperature for 20 minutes. Next, a mixed solution of 10.5 g of the target product obtained in the step (1) and 20 ml of dichloromethane was gradually added dropwise under ice cooling. After completion of the dropwise addition, the mixed solution was heated to 40 ° C. and reacted for 2 hours. Next, a mixed solution of 9.4 g sodium hydroxide and 30 ml water was added dropwise under ice cooling. After completion of the dropwise addition, the mixed solution was heated to 40 ° C. and reacted for 2 hours. After completion of the reaction, the mixed solution was ice-cooled and extracted by adding water and dichloromethane. The organic layer was washed with saturated Japanese salt water, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n-hexane Z ethyl acetate = 2Z 1), and 1- (3 black mouth 2 pyridyl) with a melting point of 93-94 ° C. ) Pyrrole-2-carbaldehyde 9.7 g (yield 79%) was obtained as a white solid.

[0080] (3) N-bromosuccinimide 7. lg was added little by little to a mixed solution of 7.5 g of the target product obtained in the above step (2) and 100 ml of dimethylformamide, and then heated to 70 ° C. Reacted for hours. After completion of the reaction, the mixed solution was ice-cooled and a saturated aqueous sodium hydrogen carbonate solution was added. After extraction twice with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n-hexane Z ethyl acetate = 3Z 1). The crude product was recrystallized from ethyl acetate hexane to obtain 4-bromo-1- (3 chloro-2-pyridine having a melting point of 128-129 ° C. Di-l) pyro-roux 2 carbaldehyde 7. lg (69% yield) was obtained as white crystals.

[0081] (4) 4.35 g of sodium chlorite, sodium dihydrogen phosphate · 2 hydrate in a mixed solution of 30 ml of the target product obtained in step (3) 1.06 gt-butanol and 30 ml of 2-methyl-2-butene A mixed solution of 4.5 g of product and 30 ml of water was gradually added dropwise, followed by stirring at room temperature for 38 hours. After completion of the reaction, 100 ml of water was added and extracted three times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1.lg (yield 100%) of 4-bromo 1- (3-chloro-2-pyridyl) pyrrole-2-carboxylic acid with a melting point of 218-220 ° C as white crystals. It was.

[0082] (5) To a mixed solution of 243 mg of methanesulfuryl chloride and 4 ml of acetonitrile, a mixed solution of 580 mg, 195 mg of triethylamine and 4 ml of acetonitrile was gradually added dropwise under ice cooling. Thereafter, the mixture was stirred at 0 ° C for 20 minutes. 5 Chloro 3-methylanthranilic acid (357 mg) was added little by little, and the mixture was stirred at 0 ° C for 5 minutes. Next, 389 mg of triethylamine was added dropwise, and the mixture was stirred at 0 ° C for 45 minutes, and then 243 mg of methanesulfonyl chloride was added dropwise. After completion of the dropwise addition, the mixed solution was reacted at room temperature for 15 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was extracted with ethyl acetate and water. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane Z ethyl acetate = 131) to give 2- [4 bromo 1- (3-chloro 2 pyridi-). 1-pyro 2-y]-6-black mouth 8-methyl 4H- 3,1-benzoxazine 4-one 125 mg (yield 15%) was obtained as white crystals.

[0083] (6) A mixed solution of 97 mg α-methyl-cyclopropylmethylamine 90 mg and 5 ml of tetrahydrofuran obtained in the step (5) was reacted for 5 hours under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was extracted with ethyl acetate and water. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-xane Z-ethyl acetate = 3Zl) to obtain the target N— [4 2 —Methyl-6 a-methyl- (cyclopropylmethyl) amino] carbol] —phenol] — 4 Bromo 1— (3-chloro-2-pyridyl) -pyrrole-2-carboxamide Compound No. 2) 99 mg (yield 86%) was obtained as white crystals. 1H NMR (400MHz, CDC1):

 3 δ ppm = 0.25-0.30 (m, 1H), 0.32-0.37 (m, 1H), 0.42-0.45 (m, 1H), 0.5 0-0.58 (m, 1H), 0.81−0.87 (m, 1H), 1.25 (t, 3H, J = 6.8Hz), 2.19 (s, 3H), 3.47 (q, 1H, J = 6.8Hz), 6.11 (d, 1H, J = 8.4Hz, NH), 7.03 (d, 1H , J = 1.6Hz), 7.08 (d, 1H, J = 1.6 Hz), 7.21 (d, 1H, J = 2.4Hz), 7.23 (d, 1H, J = 2.0Hz), 7.30 (dd, 1H, J = 4.8, 7.6Hz), 7.78 (dd, 1H, J = 4.8, 7.6Hz), 8.41 (dd, 1H, J = 1.6, 7.6Hz), 9.69 (s, 1H, NH).

 [0084] Synthesis Example 2 N— [4-Chloro-2-methyl-6] [[α-Methyl- (cyclopropylmethyl) amino] carbol] -phenol] 1— (3—Black mouth 2 Pyridyl )-Synthesis of 5-methoxyiminomethylrubyrol 2 carboxamide (compound Νο.19)

 [0085] (1) To a mixed solution of 2 g of the desired product obtained in the step (1) of Synthesis Example 1 and 30 ml of dimethylformamide, 3.77 g of N-odosuccinimide was added little by little, and then at room temperature. Reacted. After completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added. After extraction twice with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n-hexane Z ethyl acetate = 5Zl), 1- (3 black mouth 2 pyridyl) -4 odo-pyrrole 3. 4 g (99% yield) were obtained as a brown oil.

 [0086] (2) 1.3 ml of phosphorus oxychloride was gradually added dropwise to 3.8 ml of dimethylformamide under ice cooling, followed by stirring at room temperature for 20 minutes. Subsequently, a mixed solution of 3.4 g of the target product obtained in the step (1) and 15 ml of dichloromethane was gradually added dropwise under ice cooling. After completion of the dropwise addition, the mixed solution was heated to 40 ° C. and reacted for 1 hour. Under ice-cooling, a mixed solution of 2.Og sodium hydroxide and 10 ml of water was added dropwise under ice-cooling. After completion of the dropwise addition, the mixed solution was heated to 40 ° C. and reacted for 1 hour. After completion of the reaction, the mixed solution was ice-cooled and extracted by adding water and dichloromethane. The organic layer was washed with saturated Japanese salt water, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n-hexane Z ethyl acetate = 5Z2) to give 1— (3—black 2 pyridyl) —2 odopyrrole—5 —Carbaldehyde 3. Og (81% yield) was obtained as a brown solid.

[0087] (3) Target product obtained by performing step (2) several times 4.5 g Dimethyl sulfoxide 70 ml The solution was dissolved in 182 mg of palladium acetate, 335 mg of diphenylphosphinopropane, 3.4 ml of triethylamine and 6.8 ml of methanol. This mixed solution was heated to 70 ° C under a carbon monoxide atmosphere of 1 atm and reacted for 7 hours. After completion of the reaction, 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 was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n-hexane Z ethyl acetate = 3Z2), and 1- (3-chloro 2 pyridyl) 2-methoxycarbo- 2. 16 g of rubirol 5 carbaldehyde (yield 60%) were obtained as light amber crystals.

 [0088] (4) In a mixed solution of 160 mg of the target product obtained in the above step (3) and 10 ml of methanol, 76 mg of O-methylhydroxylamine hydrochloride and 74 mg of sodium acetate were added and reacted for 1 hour under reflux. It was. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: n-hexane Z-ethyl acetate = 2Z 1) and 1 (3-chloro-2-pyridyl) 5 109 mg (yield 61%) of methyl methoxyiminomethylpyrrole 2 carboxylate were obtained as a white wax-like substance.

 [0089] (5) A mixed solution of 58 mg of potassium trimethylsilanolate and anhydrous tetrahydrofuran was mixed with 108 mg of the target product obtained in the above step (4) and 1 ml of anhydrous tetrahydrofuran, and stirred at room temperature for 1 hour. After completion of the reaction, 5 ml of water was added and extracted twice with jetyl ether. The aqueous layer was adjusted to pH = 2 with 2N hydrochloric acid and extracted twice with ethyl acetate, and then the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1- (3 chloro-2-pyridyl) 5-methoxyiminomethyl bilol-2-carboxylic acid 7 2 mg (yield 70%) as a white solid.

[0090] (6) To a mixed solution of 107 mg of methanesulfuryl chloride and 5 ml of acetonitrile, a mixed solution of 238 mg of the target product obtained in the above step (5), 86 mg of triethylamine and 5 ml of acetonitrile was gradually added dropwise under ice cooling. Thereafter, the mixture was stirred at 0 ° C for 20 minutes. 5 Black mouth 1-Methyl phthalate 158 mg was added little by little, and the mixture was stirred at 0 ° C for 5 minutes. Next, 2 mg of triethylamine 17 was added dropwise and stirred at 0 ° C. for 45 minutes, and then 107 mg of methanesulfuryl chloride was added dropwise. After completion of the dropwise addition, the mixed solution was reacted at room temperature for 15 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was extracted with ethyl acetate and water. Organic layer with water and saturated saline Washed and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane Z ethyl acetate = 3/1) to give 2- [1— (3- -L) 5-Methoxyiminomethylbilol 2-yl] — 6 Black mouth 8-Methyl 4H— 3, 1-Benzoxazin 1-one 87 mg (24% yield) was obtained as a white wax-like substance. .

(7) A mixed solution of 86 mg of the target product obtained in the step (6), 9 Omg of a-methyl-cyclopropylmethylamine and 10 ml of tetrahydrofuran was reacted for 10 hours under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was extracted with ethyl acetate and water. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane Z ethyl acetate = 2Zl) to obtain the target N— [4-chloro-2-methyl-6- [ [α-Methyl (cyclopropylmethyl) amino] carbol] -phenol] — 1— (3-Chromium 1-Pyridine) -5-Methoxyiminomethylpyrrole 2 Carboxamide ( The following compound Νο.19) 28 mg (yield 27%) was obtained as a white amorphous substance. ¹ H NMR (400MHz, CDC1):

 3 δ ppm = 0.25-0.30 (m, 1H), 0.32-0.37 (m, 1H), 0.42-0.45 (m, 1H), 0.50 -0.58 (m, 1H), 0.81-0.87 (m, 1H), 1.25 (d, 3H, J = 6.8Hz), 2.13 (s, 3H), 3.47 (q, 1H, J = 6.8Hz), 3.72 (s, 3H), 6.00 (d, 1H, J = 8.0Hz, NH) , 6.76 (d, 1H, J = 4.4Hz), 7.14 (d, 1H, J = 2.8 Hz), 7.16 (s, 1H), 7.18 (d, 1H, J = 3.6Hz), 7.33 (dd, 1H, J = 3.2, 7.6Hz), 7.63 (s, 1H), 7.78 (dd, 1H, J = 2.0, 7.6Hz), 8.42 (dd, 1H, J = 1.6, 4.8Hz), 9.64 (s, 1H, NH ).

 Next, typical examples of the compound of the present invention represented by the formula (I) are listed in Table 1. These compounds can be synthesized based on the above synthesis examples or various production methods of the compound of the present invention described above. In Table 1, No. indicates the compound number. In Table 1, Me is methyl, Et is ethyl, Pr is isopropyl, c-CH is cyclopropyl, and A1 is -CH (Me) -cycl.

 3 5

 Mouth propyl, A2 — CH (Me) CH SCH CF, A3 — CH CH SCHF, A4 — CH-

2 2 3 2 2 2 2

2,2-dichloro-1-methylcyclopropyl.

[0093] [Table 1] First

2] (第 1表のつづき）

2] (Continued from Table 1)

次に試験例を記載する。

Next, test examples are described.

Test example 1 Effectiveness test for Lotus monto

Cabbage leaf pieces were dipped in a chemical solution prepared so that the concentration of the compound of the present invention was 50 ppm or 12.5 ppm for about 10 seconds and air-dried. A wet filter paper was laid on a petri dish with a diameter of 9 cm, and air-dried cabbage leaves were placed on it. There, 10 larvae of 2 to 3 years old were released, and then they were covered and left in a constant temperature room at 25 ° C. On the 5th day after release, mortality was determined, and the mortality rate was calculated using the following formula. Abnormal insects were also considered dead. The compound Nos. 2 to 9, 11 to 14, 16 to 21, 24 to 26 and 43 were determined to have a mortality rate of 50 ppm, and all compounds showed a high control effect of 90% or more. When the death rate was determined at 12.5 ppm for Compound No.l, it showed a high control effect of 90% or more. It was.

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

 [0096] Test Example 2 Medicinal efficacy test against Phytophthora tick

 On the inner surface of a 9 cm diameter petri dish, 1 ml of an acetone solution of the compound of the present invention (concentration: 10 gZml) is dropped with a micropipette. On the other hand, as a control, add 1 ml of acetone in the same manner. After the inside of the petri dish has dried, put about 100 young ticks, cover with a polyethylene sheet and seal with a rubber band. Then, leave the petri dish at 25 ° C constant temperature, 100% relative humidity, and constant conditions, except during observation. Observe 24 hours after placing the ticks in the petri dish, and record the number of rollover (knockdown) ticks after drug contact. Repeat the above operation twice.

 The rollover rate obtained from the following formula is corrected by Abbott's correction formula.

 Corrected rollover rate (%) = [(Non-rollover rate of control zone Non-rollover rate of treatment zone) Non-rollover rate of Z zone] X 100

 Treatment with the compounds of the present invention overturns most juvenile ticks.

 [0097] Test Example 3 Drug efficacy test on cat fleas

0.5 ml of an acetone solution of the compound of the present invention prepared to 10.6 ppm is dropped into a glass tube (inner diameter 2.6 cm, bottom area 5.3 cm ² , height 12 cm) with a smooth bottom. Acetone is evaporated at room temperature to form a dry film containing the compound of the present invention on the bottom surface. Ten cat fleas (C tenocephalides felis) adults (non-blood-sucking adults within 5 days after emergence) are placed therein and the compound of the present invention is exposed. The test will be conducted in triplicate.

 After 48 hours of exposure, determine whether the flea is alive or not, and determine the mortality rate in the same manner as in Test Example 1. Treatment with the compounds of the present invention kills most fleas.

 [0098] Next, formulation examples are described.

 Formulation Example 1

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

 (2) Clay 72 parts by weight

 (3) 8 parts by weight of sodium lignin sulfonate

The above is uniformly mixed to obtain a wettable powder. Formulation Example 2

 (1) Compound of the present invention

 (2) Talc

The above is uniformly mixed to form a powder.

Formulation Example 3

 (1) Compound of the present invention

 (2) N, N —Dimethylacetamide Isobe

 (3) Polyoxyethylene alkylphenol 10 layers! I

 50 parts by weight

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

Formulation Example 4

 (1) Clay 68 heavy I

 (2) Sodium sulfonate sulfonate

 (3) Polyoxyethylene alkyl aryl sulfate I

 (4) Fine silica 25 parts by weight

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

Formulation Example 5

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

 (2) Oxidated polyalkylphenyl phosphate triethanolamine

 2 parts by weight

 (3) Silicone 0.2 parts by weight

 (4) Water 47.8 parts by weight

In addition to the stock solution uniformly mixed and crushed

 (5) Sodium polycarboxylate 5 parts by weight

 (6) Anhydrous sodium sulfate 42.8 parts by weight

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

Formulation Example 6 (1) Compound of the present invention 5 parts by weight

 (2) 1 part by weight of polyoxyethylene octyl ether

 (3) Polyoxyethylene phosphate ester 0.1 parts by weight

 (4) Granular calcium carbonate 93.9 parts by weight

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

Formulation Example 7

 (1) Compound of the present invention 2.5 parts by weight

 (2) N-methyl-2-pyrrolidone 2.5 parts by weight

 (3) Soybean oil 95.0 parts by weight

Formulation example 8

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

 (2) Oxidated polyalkylphenyl phosphate triethanolamine

 2 parts by weight

 (3) Silicone 0.2 parts by weight

 (4) Xanthan Gum 0.1 parts by weight

 (5) 5 parts by weight of ethylene glycol

 (6) 52.7 parts by weight of water

The above is uniformly mixed and pulverized to obtain an aqueous suspension.

Formulation Example 9

 (1) Compound of the present invention 10 parts by weight

 (2) Diethylene glycol monoethyl ether 90 parts by weight

The above ingredients are mixed uniformly to form a solution.

Industrial applicability

The novel anthranilamides have been found to have a very high control effect against pests at a low dose, and pest control agents containing these compounds are, for example, agricultural products. It can be used as a control agent for various pests that are problematic in the horticulture field, that is, a pesticide for agricultural and horticultural use, and a pest control agent that parasitizes animals, that is, an animal parasite. The specifications, claims, and abstract of Japanese Patent Application 2005-134582 filed on May 2, 2005 and Japanese Patent Application 2006-069614 filed March 14, 2006 Is hereby incorporated by reference as a disclosure of the specification of the present invention.

Claims

(Wherein R ¹ is halogen or alkyl, R ² is a hydrogen atom, halogen, alkyl, haloalkyl, cyano or methoxycarbon, and each of R ³ , R ⁴ and R ⁵ is a hydrogen atom; Halogen; alkyl; haloalkyl; alkoxy; haloalkoxy; formyl; alkoxyalkyloxymethyl; cycloalkylcarbonyl; haloalkylcarbonyl; substituted with alkoxy, alkylamino, or dialkylamino, iminoalkyl; or 1 or 2 R ⁶ is halogen, alkyl or haloalkyl, A is a hydrogen atom; alkyl; alkylthioalkyl; haloalkylthioalkyl; alkylsulfinylalkyl; haloalkylsulfinylalkyl; alkylsulfonylalkyl; Halo Alkylsulfonylsulfonyl; or group power consisting of halogen, alkyl and haloalkyl, optionally substituted with at least one substituent selected from C cycloalkyl-alkyl, X is CR ⁷ or a nitrogen atom, R ⁷ is water  3-4 Element A, halogen, alkyl or haloalkyl, provided that (1) when A is a hydrogen atom, alkyl, alkylthioalkyl, alkylsulfinylalkyl or alkylsulfonylalkyl, any of R ³ , R ⁴ or R ⁵ 1 One is formyl; alkoxyalkyloxymethyl; cycloalkylcarbonyl; haloalkylcarbonyl; iminoalkyl optionally substituted with alkoxy, alkylamino or dialkylamino; or an alkyl substituted with 1 or 2 cyanos; ) When R ³ and R ⁵ are hydrogen atoms and R ^{4 is} halogen, haloalkyl or haloalkoxy, A is not haloalkylthioalkyl, haloalkylsulfuralkyl or haloalkylsulfonylalkyl. ) Anthranilamide-based compound represented by the following formula, its N-oxide or a salt thereof.

(Wherein IT is a halogen or alkyl, R ² is a hydrogen atom, halogen, alkyl, haloalkyl, cyano or methoxycarbon, and each of R ³ , R ⁴ and R ⁵ is a hydrogen atom; halogen Alkyl; haloalkyl; alkoxy; haloalkoxy; formyl; alkoxyalkyloxymethyl; cycloalkylcarbonyl; haloalkylcarbonyl; substituted with alkoxy, alkylamino, or dialkylamino; iminoalkyl; or 1 or 2; Aruke substituted with Shiano - a le, R ⁶ is halogen, alkyl or haloalkyl, a is a hydrogen atom, alkyl, alkylthioalkyl; Haroaruki thio alkyl; alkylsulfinylalkyl; haloalkylsulfinyl alkyl; alkylsulfonylalkyl; halo Le Kill sulfonyl alkyl; or halogen, O be substituted with at least one substituent selected group force consisting completion alkyl and haloalkyl, C cycloalkyl - alkyl, X is CR ⁷ or nitrogen atom, R ⁷ is water  3-4 Element A, halogen, alkyl or haloalkyl, provided that (1) when A is a hydrogen atom, alkyl, alkylthioalkyl, alkylsulfinylalkyl or alkylsulfonylalkyl, any of R ³ , R ⁴ or R ⁵ 1 One is formyl; alkoxyalkyloxymethyl; cycloalkylcarbonyl; haloalkylcarbonyl; iminoalkyl optionally substituted with alkoxy, alkylamino or dialkylamino; or an alkyl substituted with 1 or 2 cyanos; ) When R ³ and R ⁵ are hydrogen atoms and R ^{4 is} halogen, haloalkyl or haloalkoxy, A is not haloalkylthioalkyl, haloalkylsulfuralkyl or haloalkylsulfonylalkyl. ) Anthranilamide compound represented by the following formula (1) Formula (Π): [Chemical 3]

(Where

R and A are as described above) and the formula (III): [Chemical 4]

(In the formula, Z is a chlorine atom, —OH or C alkoxy, R, R, R ⁵ , R and X are  1-4 Force to react with a compound represented by formula (IV): [Chemical 5]

(Where

R ⁶ and X are as described above) and a compound represented by the formula (V): A-NH (wherein A is as described above) Feature method.  [3] A pest control agent comprising as an active ingredient the anthranilamido compound of claim 1, its N-talide oxide or a salt thereof.  [4] An agricultural and horticultural pest control agent comprising the anthranilamide compound of claim 1, its N-oxide or a salt thereof as an active ingredient. [5] An animal parasite control agent comprising the anthranilamide compound of claim 1, its N-oxide or a salt thereof as an active ingredient. [6] A method for controlling pests by applying an effective amount of the anthranilamide compound of claim 1, its N-oxide or a salt thereof.