JP2001302606A - Phenacyl derivative, method for producing the same and pest control agent containing thereof - Google Patents

Abstract

PROBLEM TO BE SOLVED: To solve problems that, though a large number of pest control agents are used, their effects are insufficient, their uses are limited as the pest acquire resistance, they have strong toxicity to humans, animals and fishes, they disturb an ecological system by their remaining and so forth, thus, develop a novel pest control agent high in safety with having little aforesaid defects. SOLUTION: This phenacylamine derivative is expressed by general formula I [A is an alkyl, cycloalkyl, (substituted) phenyl, pyridyl or pirazolyl; R1 and R2 express each an alkyl or together form a 3-6 membered carbon ring; R3 expresses H, an alkyl, alkoxyalkyl, alkylthioalkyl or COR4; X expresses a halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, nitro, cyano, (substituted) phenol, phenoxy, benzyloxy, pyridyloxy or the like; n expresses 0-5 integer]. Its salt is also claimed.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel phenacylamine derivative useful as an active ingredient of a pesticidal agent.

[0002]

2. Description of the Related Art Japanese Patent Publication No. 48-18222 discloses a method for producing an acylaminoketone derivative, but specific description relating to a phenacylamine derivative represented by the following formula (I) is found. Absent. Further, the publication does not disclose any usefulness as a pest controlling agent described later.

[0003]

Many pest control agents have been used for many years, but their efficacy is insufficient, and pests gain resistance and their use is restricted. There are many things that have various problems, such as high toxicity and disturbing ecosystems due to persistence. Therefore, development of a novel safe pesticide with few such defects is desired. Animal parasites include livestock,
Parasitic on the body surface of pets, stomach, intestinal tract, lung, heart, liver, blood vessels, subcutaneous, lymphatic tissues, etc., anemia, malnutrition, weakness,
Since various animal diseases such as weight loss and damage to the intestinal tract wall, various organs, and other tissues are caused, their control is desired.

[0004]

Means for Solving the Problems The present inventors have conducted various studies on phenacylamine derivatives in order to find a better pest control agent. As a result, they have found that the novel phenacylamine derivatives and salts thereof have a very high control effect on pests at a low dose and have almost no adverse effect on mammals, fish, and the like. Completed the invention. That is, the present invention provides a compound represented by the formula (I):

[0005]

Embedded image Wherein A is alkyl, cycloalkyl, phenyl optionally substituted with Y, pyridyl optionally substituted with Y or pyrazolyl optionally substituted with Y,
R ₁ and R ₂ are each alkyl, R ₁ and R ₂ may together form a 3- to 6-membered saturated carbocyclic ring, and R ₃ is a hydrogen atom, alkyl, alkoxyalkyl, alkylthioalkyl or A COR ₄ group, R ₄ is alkyl or alkoxy, X is halogen, alkyl, haloalkyl,
Alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio, alkynylthio,
Haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl optionally substituted with Y, phenoxy optionally substituted with Y, substituted with Y Benzyloxy or pyridyloxy optionally substituted with Y, wherein Y is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylamino Sulfonyl, nitro or cyano, n is an integer of 0 to 5, and when n is 2 or more,
Xs may be the same or different, provided that A is unsubstituted phenyl, R ₁ and R ₂ are each methyl or together form a 6-membered saturated carbocycle, and R ₃ is A hydrogen atom and n is 0), or a salt thereof, a method for producing them, and a pesticidal agent containing them.

The alkyl or alkyl moiety in A, R ₁ , R ₂ , R ₃ , R ₄ , X and Y is a straight-chain or branched one having 1 to 6 carbon atoms, for example, methyl, ethyl, Propyl, isopropyl, butyl, tert-butyl, pentyl,
Hexyl and the like.

The cycloalkyl in A has 3 carbon atoms.
~ 6, such as cyclopropyl, cyclopentyl,
Cyclohexyl and the like.

The alkenyl or alkenyl moiety in X is a straight or branched one having 2 to 7 carbon atoms, for example, vinyl, 1-propenyl, allyl, isopropenyl, 1-
Butenyl, 1,3-butadienyl, 1-hexenyl, 1
-Heptenyl and the like. The alkynyl or alkynyl moiety in X is a straight-chain or branched one having 2 to 7 carbon atoms, for example, ethynyl, 2-butynyl,
Pentynyl, 3-hexynyl, 4-dimethyl-2-pentynyl and the like.

Phenyl optionally substituted with Y in A, pyridyl optionally substituted with Y, pyrazolyl optionally substituted with Y, phenyl optionally substituted with Y in X, The number of substituents Y of phenoxy optionally substituted by Y, benzyloxy optionally substituted by Y and pyridyloxy optionally substituted by Y may be 1 or 2 or more, and In such a case, these substituents may be the same or different.

The halogen in X and Y or the halogen as a substituent includes each atom of fluorine, chlorine, bromine or iodine. The number of halogens as a substituent is 1 or 2
The number of halogens may be the same or different. The substitution position of halogen may be any position.

Salts of the phenacylamine derivative represented by the above formula (I) include all salts that are agriculturally acceptable, for example, alkali metal salts such as sodium salts and potassium salts; Alkaline earth metal salts such as magnesium salt and calcium salt; ammonium salts such as dimethylamine salt and triethylamine salt; inorganic acid salts such as hydrochloride, perchlorate, sulfate and nitrate; acetate, methanesulfone Organic acid salts such as acid salts. The phenacylamine derivative represented by the formula (I) has optical isomers, and the present invention includes both isomers and isomer mixtures.

The phenacylamine derivative represented by the above formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) is produced according to the following reaction [A] or [B] or a conventional method for producing a salt. be able to.

[0013]

Embedded image

In the reaction [A], A, R ₁ , R ₂ , X and n are as described above. Z is hydroxy, alkoxy or halogen, and examples of the halogen include fluorine, chlorine, bromine and iodine atoms. The reaction [A] is usually performed in the presence of a base and a solvent.

Examples of the base include alkali metals such as sodium and potassium; alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tertiary butyrate; carbonates such as sodium carbonate and potassium carbonate; Bicarbonates such as sodium carbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; monomethylamine, dimethylamine and triethylamine One or more amines are appropriately selected from pyridines such as pyridine and 4-dimethylaminopyridine. The base is
1 to 3 moles, preferably 1 mole, relative to the compound of the formula (II)
Use up to 2 times the mole.

The solvent may be any solvent as long as it is inert to the reaction, for example, benzene, toluene,
Aromatic hydrocarbons such as xylene and chlorobenzene;
Aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; dioxane;
Ethers such as tetrahydrofuran and diethyl ether; esters such as methyl acetate and ethyl acetate; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone, pyridine; acetonitrile, One or two or more of nitriles such as pionitrile and acrylonitrile; ketones such as acetone and methyl ethyl ketone are appropriately selected.

The reaction [A] is carried out in the presence of a dehydrating condensing agent, if necessary. Examples of the dehydrating condensing agent include N, N'-dicyclohexylcarbodiimide. Reaction [A]
Is usually 0 to 100 ° C., preferably 0 to 50 ° C., and the reaction time is usually 0.5 to 48 hours, preferably 1 to 2 hours.
4 hours.

[0018]

Embedded image

In the reaction (B), A, R ₁ , R ₂ , X and n are as described above, and R ₃ ′ is an alkyl, alkoxyalkyl, alkylthioalkyl or COR ₄ group (R ₄ is as described above)
W is halogen, and fluorine is fluorine,
Each atom of chlorine, bromine or iodine is mentioned.

The reaction [B] is usually performed in the presence of a base and a solvent. Examples of the base include alkali metals such as sodium and potassium; alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tertiary butyrate; carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate; Bicarbonates such as potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine and triethylamine Classes: One or more pyridines such as pyridine and 4-dimethylaminopyridine are appropriately selected. The base is used in an amount of 1 to 3 times, preferably 1 to 1.5 times the mole of the compound of the formula (I-1).

The solvent may be any solvent as long as it is inert to the reaction, for example, benzene, toluene,
Aromatic hydrocarbons such as xylene and chlorobenzene;
Aliphatic hydrocarbons such as carbon tetrachloride, methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; dioxane;
Ethers such as tetrahydrofuran and diethyl ether; esters such as methyl acetate and ethyl acetate; polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone, pyridine; acetonitrile, One or two or more of nitriles such as pionitrile and acrylonitrile; ketones such as acetone and methyl ethyl ketone are appropriately selected.

The reaction temperature of the reaction (B) is usually from 0 to 100.
° C, desirably from 0 to 50 ° C, and the reaction time is usually from 1 to
It is 300 hours, desirably 1 to 150 hours.

The compound of the formula (II) used in the reaction [A] is novel and can be produced according to the following reaction [C] or [D].

[0024]

Embedded image

In the reaction [C], R ₁ , R ₂ , X and n are as described above. In the reaction [C], a salt of the compound (II) can be produced according to post-treatment of the reaction or according to a usual salt formation reaction. Reaction [C] is usually performed in the presence of an oxidizing agent and a solvent. Examples of the oxidizing agent include potassium ferricyanide. The oxidizing agent is used in an amount of 1 to 10 times, preferably 1 to 5 times the mole of the compound of the formula (V).

The solvent may be any solvent as long as it is inert to the reaction, for example, ethers such as dioxane, tetrahydrofuran and diethyl ether; esters such as methyl acetate and ethyl acetate; dimethyl sulfoxide, sulfolane Polar aprotic solvents such as dimethylacetamide, dimethylformamide, N-methylpyrrolidone, and pyridine; nitriles such as acetonitrile, propionitrile, and acrylonitrile; ketones such as acetone and methyl ethyl ketone; Two or more are appropriately selected.

The reaction temperature of the reaction (C) is usually from 20 to 150
℃, desirably 50-100 ℃, the reaction time is usually 0.5
-30 hours, desirably 1-20 hours.

[0028]

Embedded image

In the reaction [D], R ₁ , R ₂ , X and n are as described above. In the reaction [D], a salt of the compound (II) can be produced according to post-treatment of the reaction or a conventional salt forming reaction. The cyclization reaction of the reaction [D] is usually performed in the presence of a base and a solvent.

Examples of the base include alkali metals such as sodium and potassium; alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tert-butylate; and metal hydrogen such as sodium hydride and potassium hydride. One or two or more compounds are appropriately selected from compounds and the like. The base is used in an amount of 1 to 3 times, preferably 1 to 1.5 times the mole of the compound of the formula (VI).

The solvent may be any solvent as long as it is inert to the reaction, for example, benzene, toluene,
Aromatic hydrocarbons such as xylene and chlorobenzene;
Ethers such as dioxane, tetrahydrofuran and diethyl ether; alcohols such as methanol, ethanol, propanol and tert-butanol; one or two or more types are appropriately selected from nitriles such as acetonitrile, propionitrile and acrylonitrile. Is done.

The reaction temperature of the cyclization reaction of the reaction [D] is usually 0 to 150 ° C., preferably 30 to 100 ° C., and the reaction time is as follows:
It is usually 0.5 to 24 hours, preferably 1 to 12 hours.

The hydrolysis reaction [D] may be performed according to a general hydrolysis reaction, and is usually performed in the presence of an acid or a base and a solvent.

Examples of the acid include hydrogen chloride and sulfuric acid. Examples of the base include metal hydroxides such as sodium hydroxide and potassium hydroxide.
As the solvent, any solvent may be used as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and tert-butanol; acetonitrile, propionitrile and nitriles such as acrylonitrile; acetone, One or more ketones such as methyl ethyl ketone; water and the like are appropriately selected.

The reaction temperature of the hydrolysis reaction of the reaction [D] is usually from 0 to 100 ° C., preferably from 20 to 80 ° C.
It is usually 0.1 to 12 hours, preferably 0.1 to 1 hour.

The compound of the formula (VI) used in the above reaction [D] is novel and can be produced according to the following reaction [E].

[0037]

Embedded image

In the reaction [E], R ₁ , R ₂ , X and n are as described above. Reaction [E] is 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, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane Aliphatic hydrocarbons such as cyclohexane and cyclohexane; ethers such as dioxane, tetrahydrofuran and diethyl ether; esters such as methyl acetate and ethyl acetate; alcohols such as methanol, ethanol, propanol and tert-butanol; acetonitrile , Propionitrile, nitriles such as acrylonitrile; acetone,
One or more of ketones such as methyl ethyl ketone are appropriately selected.

The methyl iodide of the reaction [E] is used in an amount of 1 to 10 times, preferably 1 to 3 times the mole of the compound of the formula (VII). Also, methyl iodide can double as a solvent if used in excess. The reaction temperature of the reaction (E) is usually 0 to 1
00 ° C, desirably 10 to 50 ° C, and the reaction time is usually 0.
It is 5 to 48 hours, desirably 1 to 24 hours.

The compound of the formula (VII) used in the reaction [E] is novel and can be produced according to the following reaction [F].

[0041]

Embedded image

In the reaction [F], R ₁ , R ₂ , X and n are as described above. The reaction [F] may be performed according to a general hydrazone synthesis reaction, and may be performed in the presence of a dehydrating agent and / or a catalyst as necessary.

Examples of the dehydrating agent include molecular sieves. The dehydrating agent is usually used 1 to 30 times, preferably 5 to 10 times the weight of the compound of the formula (V). Examples of the catalyst include titanium tetrachloride. The dimethylhydrazine of the reaction [F] is generally used in a molar amount of 1 to 30 times, preferably 5 to 10 times the molar amount of the compound of the formula (V).

The reaction temperature of the reaction (F) is usually 20 to 150
℃, desirably 50 to 120 ℃, the reaction time is usually 5 ~
200 hours, desirably 24-120 hours.

Preferred embodiments of the pesticidal composition containing the compound of the present invention are described below. The pesticidal agent containing the compound of the present invention is particularly useful as an insecticide, acaricide, nematicide, soil insecticide, for example, spider mite, spider mite, Kanzawa spider mite, mandarin spider mite, apple spider mite, Dermatophagoides farinae, mandarin mite. , Plant parasitic mites such as spider mite; aphids such as peach aphid, cotton aphid, cotton moth, armyworm, tobacco cutworm, codling moth, ball worm, tobacco bud worm, gypsum, mob beetle, chanokomakumamaki, colorado potato beetle Agricultural insect pests such as, beetles, ballweed, planthoppers, leafhoppers, scale insects, stink bugs, whiteflies, thrips, grasshoppers, flower flies, scarab beetles, tamanayaga, kaburayaga, ants, etc .; Plant-parasitic nematodes, such as mosquitoes, cyst nematodes, nematodes, rice shining nematodes, strawberry nematodes, pine wood nematodes; gastropods, such as slugs, snails, etc .; Soil pests such as legs; hygiene pests such as house dust mites, cockroaches, houseflies, mosquitoes; and storage pests such as bark moth, azuki weevil, skull, and beetles; termites, termites, termites It is effective for controlling clothing such as insects, house pests, and indoor dust mites such as Dermatophagoides farinae, Dermatophagoides farinae, and red mites. Among them, pest control agents containing the compound of the present invention are particularly effective for controlling agricultural pests, plant parasitic nematodes, and the like. The pesticidal composition containing the compound of the present invention is also effective for controlling various pests that are resistant to drugs such as organophosphorus agents, carbamate agents and synthetic pyrethroid agents. Further, since the compound of the present invention has excellent systemic migration properties, by treating a soil with a pest controlling agent containing the compound of the present invention, soil harmful insects, mites, nematodes, gastropods can be obtained. At the same time as controlling insects and isopods, pests in the foliage can be controlled.

As another desirable embodiment of the pesticidal composition containing the compound of the present invention, the above-mentioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests and the like are comprehensively used. A pest control agent for agriculture and horticulture to be controlled is included.

The pesticidal composition containing the compound of the present invention is usually prepared by mixing the compound with various agricultural auxiliaries to prepare powders, granules, wettable powders, wettable powders, aqueous suspensions, oils, etc. Suspensions, aqueous solvents, emulsions, solutions, pastes, aerosols,
It is used by being formulated in various forms such as micro-sprays,
As long as it meets the purpose of the present invention, it can be in any of the usual formulation forms used in the art. As auxiliary agents used in the preparation, solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, a mixture of 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, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, alcohol; fatty acid salts, benzoic acid Acid salt, alkyl sulfosuccinate, dialkyl sulfosuccinate, polycarboxylate, alkyl sulfate, alkyl sulfate, alkylaryl sulfate, alkyl diglycol ether sulfate, alcohol 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 Surfactants and spreading agents, such as salts of naphthalenesulfonic acid formalin condensate; sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerols , 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, polyoxyethylene fatty acid ester Nonionic surfactants and spreading agents such as polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hardened castor oil, polyoxypropylene fatty acid ester; olive oil, kapok oil, castor oil, palm oil Oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, cutting oil, liquid Vegetable oils such as paraffin and mineral oils are exemplified.
These adjuvants can be selected from those known in the art without departing from the purpose of the present invention. In addition, extenders, thickeners, anti-settling agents, anti-freezing agents,
Various auxiliary agents usually used such as a dispersion stabilizer, a safener, a fungicide and the like 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, they can be used as they are, or can be used after being diluted to a predetermined concentration with a diluent such as water and adding various spreading agents as necessary.

The application of the pesticidal composition containing the compound of the present invention cannot be specified unconditionally due to differences in weather conditions, preparation form, application time, place of application, types and occurrence of pests, etc., but generally 0.05 to 800,000 ppm, Desirably 0.5 to 5000
The concentration of the compound of the present invention is 0.05 to 5000 per hectare per unit area.
0 g, preferably 1-30000 g. Further, the application of the pesticidal composition for agricultural and horticultural use, which is another desirable embodiment of the pesticidal composition containing the compound of the present invention, is performed in accordance with the application of the pesticidal composition. The present invention also includes a method for controlling pests by such an application method, particularly a method for controlling agricultural pests and plant parasitic nematodes.

The application of various formulations of the pesticidal agent containing the compound of the present invention, or a dilution thereof, is carried out by a generally applied application method, that is, application (eg, application, spraying, misting, atomizing, atomizing, etc.). Granulation, surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, dressing, coating, etc.), immersion poison bait, etc. Further, the livestock is fed with the active ingredient mixed with feed,
It is also possible to inhibit the generation and growth of pests, especially pests, in the excrement. It can also be applied by the so-called ultra-low concentration small volume spraying method (ultra low volume). In this method, it is possible to contain 100% of the active ingredient.

The pesticidal composition containing the compound of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, chemical mitigation agents, etc., and in this case, it shows more excellent effect and action. There is. Other pesticides include herbicides, insecticides, acaricides, nematicides, soil pesticides, fungicides, antivirals, 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 kinds of active ingredient compounds of other pesticides are mixed or used in combination, the application range, the timing of chemical treatment, the control activity, etc. in a favorable direction. It is possible to improve. The compound of the present invention and the active ingredient compound of another pesticide may be separately prepared and used by mixing at the time of spraying, or both may be prepared and 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 another pesticide,
Although it cannot be specified unconditionally due to differences in weather conditions, formulation form, application time, application place, types of pests and outbreaks,
Generally, it is 1: 300 to 300: 1, preferably 1: 100 to 100: 1. The appropriate application amount is 0.1 to 50,000 g, preferably 1 to 30,000 g, as the total amount of the active ingredient compound per hectare. The present invention also includes a method for controlling pests by a method for applying such a mixed pest control composition.

Examples of the pesticides, acaricides, nematicides or soil pesticides in the other pesticides, that is, the active ingredient compounds of the pesticides (generic names; including some applications) include, for example, Profenofos, Dichlorvos (Dichl
orvos), Fenamiphos, Fenitrothion
(Fenitrothion), EPN, diazinon (Diazinon), chlorpyrifos-methyl (Chlorpyrifos-methyl), acephate (Acephate), prothiophos (Prothiofos), phosthiazate (Fosthiazate), phosphocarb (Phosphocarb), cassaphos (Cadusafos), disulphoton (Disfoton) Organic phosphate compounds;

Carbaryl, propoxur (Pro
poxur), Aldicarb, Carbofuran (Carbofuran)
furan), Thiodicarb, Methomyl (Methomy)
l), Oxamyl, Ethiophenecarb (Ethiofe
ncarb), pirimicarb (Pirimicarb), fenobucarb (F
carbamate compounds such as enobucarb), Carbosulfan, Benfuracarb;

Cartap, Thioclam (Thioc)
Nelyistoxin derivatives such as yclam); Dicofol (Dic
ofol), organochlorine-based compounds such as Tetradifon; organometallic-based compounds such as fenbutatin oxide (Fenbutatin Oxide); fenvalerate (Fenvalerat)
e), Permethrin, Cypermethrin (Cyper
pyrethroid compounds such as methrin), deltamethrin, cyhalothrin, tefluthrin, ethofenprox;

Diflubenzuron, chlorfluazuron, teflubenzuron (T
eflubenzuron), benzoylurea-based compounds such as Flufenoxuron; Methoprene (Methopr)
ene) like juvenile hormone-like compounds; Pyridabene (Pyrid
aben) pyridazinone-based compounds; fenpyroximate, fipronil, tebufenpyrad, ethiprole
le), pyrazole-based compounds such as Tolfenpyrad;

[0055] Imidacloprid, Nitenpyram, Acetamiprid,
Thiacloprid, Thiamethoxam (Thiame
neooxatinoids such as thoxam), clothianidin, and dinotefuran; Tebufenozide, methoxyfenozide
hydrazine-based compounds such as nozide) and chromafenozide;

As a dinitro compound, an organic sulfur compound, a urea compound, a triazine compound, a hydrazone compound and other compounds, buprofezin (Buprofezi
n), Hexythiazox, Amitraz (Amit
raz), Chlordimeform, Silafluofen, Triazamate,
Pymetrozine, Pyrimidifen
fen), chlorfenapyr (Chlorfenapyr), indoxacarb (Indoxacarb), acequinocyl (Acequinocyl), ethoxazole (Etoxazole), cyromazine (Cyromazine),
Compounds such as 1,3-dichloropropene; and the like. Furthermore, microbial pesticides such as BT agents, entomopathogenic virus agents, etc., avermectin
(Avermectin), milbemectin (Milbemectin), antibiotics such as spinosad (Spinosad) and the like can be mixed and used in combination.

Examples of the active ingredient compounds of the fungicides (generic names; partially included) in the other pesticides include, for example, mepanipyrim (Mepanipyrim) and pyrimethanil (Pyrimethani).
l), pyrimidinamine-based compounds such as cyprodinil;

[0058] Triadimefon, Bitertanol, Triflumizol
e), etaconazole, propiconazole
(Propiconazole), Penconazole (Penconazole), Flusilazole (Flusilazole), Microbutanyl (Myclobut
anil), cyproconazole, terbuconazole, hexaconazole
le), furconazole-cis, prochloraz (Prochloraz), metconazole (Metconazole),
Epoxiconazole, Tetraconazole, Oxpoconazole
le), azole compounds such as Sipconazole;

Quinoxaline-based compounds such as quinomethionate; Maneb, Zineb
(Zineb), Mancozeb, Polycarbamate (Polycarbamate)
dithiocarbamate compounds such as carbamate) and propineb; organic chlorinated compounds such as fthalide, chlorothalonil and quintozene; benomyl, thiophanate-methyl and carbendazim (Car
bendazim), an imidazole compound such as 4-chloro-2-cyano-1-dimethylsulfamoyl-5- (4-methylphenyl) imidazole;

Pyridinamine compounds such as Fluazinam; cyanoacetamide compounds such as Cymoxanil; Metalaxyl
l), Oxadixyl, Off-race (Ofurac
e), Benalaxyl, Furalaxyl
l), a phenylamide-based compound such as Cyprofuram; a sulfenic acid-based compound such as dichlofluanid; cupric hydroxid
e), copper-based compounds such as organic copper (Oxine Copper);

Hydroxyisoxaz
ole), isoxazole-based compounds such as fosetyl aluminum (Fosetyl-Al), and tulcofos-Meth.
yl), S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, organic phosphorous compounds such as aluminum ethyl hydrogen phosphonate; Captan (Capta)
n), N-halogenothioalkyl compounds such as Captafol and Folpet; dicarboximide compounds such as Procymidone, Iprodione and Vinclozolin;

Flutolanil, mepronil (M
epronil), benzanilide compounds such as Zoxamide; piperazine compounds such as Triforine; pyridine compounds such as Pyrifenox; fenarimol, Flutriafol Such carbinol compounds;
Piperidine compounds such as fenpropidine;

Morpholine compounds such as fenpropimorph; fentin hydroxide (F
entin Hydroxide), fentin acetate (FentinAceta
organotin-based compounds such as te);
urea compounds such as uron); Dimethomor (Dimethomor)
ph); phenyl carbamate-based compounds such as Diethofencarb;

Cyanopyrrole-based compounds such as Fludioxonil and Fenpiclonil; Azoxystrobin, Kresoxim-Methyl, Metominophen
fen), strobilurin-based compounds such as trifloxystrobin, picoxystrobin; oxazolidinone-based compounds such as famoxadone; thiazolecarboxamide-based compounds such as ethaboxam;

Silylamide compounds such as Silthiopham; Iprovalicarb
Amino acid amide carbamate compounds such as
Imidazolidine-based compounds such as phenamidone; hydroxyanilide-based compounds such as fenhexamid; Flusulfamid
benzenesulfonamide compounds such as e);

Atraquinone compounds; crotonic acid compounds; antibiotics and other compounds such as isoprothiolane, tricyclazol
e), Pyroquilon, Diclomezi
ne), probenazole (Pro.benazole), quinoxyfen
(Quinoxyfen), Propamocarb Hyd
rochloride), spiroxamine (Spiroxamine), chlorpicricin (Chloropicrin), dazomet (Dazomet), carbam sodium salt (Metam-sodium); and the like.

Other pesticides that can be mixed or used in combination with the compound of the present invention include, for example, Farm Chemicals
Active compounds of herbicides as described in the Handbook (1998 edition), especially those of the soil treatment type.

The pest controlling agent containing the compound of the present invention is useful as an agent for controlling an animal parasite, particularly as a controlling agent for an animal endoparasite or a controlling agent for an animal disease caused by a parasite. 1) Dermatophagoides mite, Mesostigmatide, scalpy, tsutsugamushi, Haemaphysalis longicornis,
Mites such as cattle tick; fleas such as cat flea, dog flea, rat flea, keoptone flea, human flea;
Louses such as bovine lice, horse lice, sheep lice, bovine lice and head lice; lice such as dog lice; lice such as blood sucking dipteran pests such as bovine pigeons, eucalyptium, and swordfish; (2) lung Nematodes such as insects, venturi, nodular worms, gastric parasites, roundworms, filamentous worms, etc .; It is effective in controlling parasites that infest the body of the host animal.

The compound of the present invention is usually used in the form of powders, granules, granules, tablets, powders, capsules, solutions, emulsions and the like together with a suitable carrier. Suitable carriers include those utilized in feed drugs and the like, such as lactose,
Examples include sucrose, glucose, starch, barley flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other commercially available feed materials. In addition, the compound of the present invention, together with a carrier, various vitamins, minerals, amino acids, enzyme preparations,
It can also be used in combination with antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, fragrances, preservatives and the like. The concentration of the compound of the present invention varies depending on the target parasite to be controlled, the method of administration, the purpose of administration, the disease symptoms, and the like. However, when the compound is administered in a feed, the concentration is usually 0.1 ppm or more. Is appropriate.

The compound of the present invention can be controlled against animal parasites such as fleas, coccidium and filamentous worms by tests according to the test methods described in, for example, JP-A-5-70350 and JP-T-11-500439. Show the effect.

Another preferred embodiment of the present invention is as follows. [1] In the above formula (I), X is halogen, alkyl,
Haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, alkylthio, haloalkylthio,
Haloalkenylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl optionally substituted with Y, phenoxy optionally substituted with Y or Y
A phenacylamine derivative which is pyridyloxy optionally substituted with or a salt thereof.

[2] In the above formula (I), X is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano A phenoxyamine derivative which is phenoxy optionally substituted with Y or pyridyloxy optionally substituted with Y, or a salt thereof.

[3] In the above formula (I), A is phenyl optionally substituted with Y, R ₁ and R ₂ are each alkyl, R ₃ is a hydrogen atom, X is halogen,
Haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, Y
Phenoxy or pyridyloxy optionally substituted with Y, Y is a halogen, alkyl, haloalkyl, haloalkoxy or haloalkylthio, and phenacylamine wherein n is an integer of 1 to 3 Derivatives or salts thereof.

[0074]

EXAMPLES Next, examples of the present invention will be described, but the present invention is not limited to these examples. First, a synthesis example of the compound of the present invention will be described.

Synthesis Example 1 Synthesis of 3,5-dichloro-N-[(4′-ethyl-1,1-dimethyl) phenacyl] benzamide (Compound No. 1-84) (1) 360 ml of water heated to 80 ° C. Potassium ferricyanide 41
g and then 5.5 g of 4-ethylisobutyrophenone 2
50 ml of 8% aqueous ammonia is added dropwise over 30 minutes, and at 85 to 90 ° C.
The reaction was performed for 16 hours. The reaction mixture was extracted with ethyl acetate and concentrated under reduced pressure. The residue was diluted with water, acidified with hydrochloric acid, and washed with ethyl acetate. The aqueous layer was neutralized with aqueous NaOH, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate.
After concentration under reduced pressure, 0.54 g of oily α-amino-4-ethylisobutyrophenone was obtained. The NMR spectrum data of this is as follows. ¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz) 1.24 (t, 3H), 1.53 (s, 6H), 2.66 (q, 2H), 7.22 (d, 2H), 7.87
(d, 2H),

(2) 0.13 g of triethylamine was added to a mixture of 0.16 g of α-amino-4-ethylisobutyrophenone and 4 ml of dichloroethane, and 0.18 g of 3,5-dichlorobenzoyl chloride was added under ice cooling, followed by 6 hours at room temperature. Reacted. The reaction mixture was poured into water, extracted with methylene chloride, and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 15/85).
0.12 g of the desired product having a melting point of 176-177 ° C. was obtained. NM of this thing
The R spectrum data is as follows. ¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz) 1.23 (t, 3H), 1.86 (s, 6H), 2.67 (q, 2H), 7.24 (dd, 2H), 7.38
(s, 1H), 7.46 (d, 2H), 7.59 (d, 2H), 7.89 (dd, 2H)

Synthesis Example 2 Synthesis of 2-chloro-N-[(4′-chloro-1,1-dimethyl) phenacyl] benzamide (Compound No. 1-54) (1) 5.92 g of 4-chloroisobutyrophenone, N A mixture of 19.5 g of N-dimethylhydrazine and 29.6 g of molecular sieve (3A) was reacted in an autoclave at 100 ° C. for 110 hours. The reaction mixture was diluted with methylene chloride and filtered. The filtrate was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give an oil.
5.82 g of 4-chloroisobutyrophenone dimethylhydrazone
I got The NMR spectrum data of this is as follows. ¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz) 1.05 (d, 6H), 2.31 (bs, 6H), 2.85 (m, 1H), 7.14 (d, 2H), 7.32
(d, 2H)

(2) 7.82 g of methyl iodide was added to a mixture of 5.82 g of 4-chloroisobutyrophenone dimethylhydrazone and 3.5 ml of absolute ethanol, and reacted at room temperature for 15 hours. Ether was added to the residue obtained by concentrating the reaction mixture under reduced pressure, and the mixture was stirred. The precipitated solid was collected by filtration, washed with ether, and dried to obtain 10.19 g of methyl 4-chloroisobutyrophenone dimethylhydrazine iodide having a melting point of 107 to 112 ° C. The NMR spectrum data of this is as follows. ¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz) 1.13 (d, 6H), 2.83 (m, 1H), 3.58 (s, 9H), 7.28 (d, 2H), 7.53
(d, 2H)

(3) 4-chloroisobutyrophenone dimethylhydrazine methyl iodide (10.19 g) and anhydrous methanol (35)
0.70 g of sodium and 15 m of anhydrous methanol
After the sodium methoxide solution prepared from l was added dropwise at room temperature, the mixture was reacted under reflux for 3 hours. The reaction mixture was concentrated under reduced pressure, and water and then hydrochloric acid were added to the residue to make it weakly acidic.
Stirred for minutes. The resulting solid was collected by filtration and dried to obtain 2.46 g of α-amino-4-chloroisobutyrophenone hydrochloride (melting point: 275 ° C./decomposition). On the other hand, the filtrate was washed with methylene chloride and then neutralized with aqueous NaOH. After extraction with methylene chloride, the extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 0.77 g of oily α-amino-4-chloroisobutyrophenone. The NMR spectrum data of this is as follows. ¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz) 1.58 (s, 6H), 7.41 (d, 2H), 7.96 (d, 2H)

(4) 0.47 g of triethylamine was added to a mixture of 0.77 g of α-amino-4-chloroisobutyrophenone and 22 ml of dichloroethane, and a mixture of 0.68 g of 2-chlorobenzoyl chloride and 3 ml of dichloroethane was added dropwise at room temperature. After the completion of the dropwise addition, the reaction was carried out at the same temperature for 15 hours. The reaction mixture was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 3/7) to obtain 1.05 g of the desired product having a melting point of 99 to 102 ° C. The NMR spectrum data of this is as follows. ^{1 H-NMR δppm (Solvent:} CDCl 3 / 400MHz) 1.76 (s, 6H), 6.98 (s, 1H), 7.26 (dd, 1H), 7.30~7.42 (m, 5
H), 7.97 (dd, 2H)

Synthesis Example 3 Synthesis of 3,5-dichloro-N-[(4′-chloro-1,1-dimethyl) phenacyl] benzamide (Compound No. 1-63) α-amino-4-chloroisobutyrophenone hydrochloride 0.47 g of triethylamine was added to a mixture of 0.49 g of salt and 14 ml of dichloroethane at room temperature, followed by 0.45 g of 3,5-dichlorobenzoyl chloride.
4 g was added and reacted at the same temperature for 15 hours. The reaction mixture was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure.
N-Hexane was added to the obtained residue, and the solid was collected by filtration and dried to obtain 0.46 g of the desired product having a melting point of 169 to 171 ° C. The NMR spectrum data of this is as follows. ^{1 H-NMR δppm (Solvent:} CDCl 3 / 400MHz) 1.79 (s, 6H), 7.04 (s, 1H), 7.36 (dd, 2H), 7.50 (s, 1H), 7.54
(d, 2H), 7.91 (dd, 2H)

Synthesis Example 4 Synthesis of 2-chloro-N-[(3 ′, 4′-dichloro-1,1-dimethyl) phenacyl] benzamide (Compound No. 1-78) α-amino-3,4-dichloro Isobutyrophenone 0.22 g, 2-
At room temperature, a mixture of 0.148 g of chlorobenzoic acid and 8 ml of dichloromethane was added with 0.215 g of N, N'-dicyclohexylcarbodiimide at room temperature.
g and 7 ml of dichloromethane were added dropwise at the same temperature.
Allowed to react for hours. The reaction mixture was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue is subjected to silica gel column chromatography (developing solvent: ethyl acetate
/ n-hexane = 3/7) to obtain 0.26 g of the desired product having a melting point of 116 to 120 ° C. The NMR spectrum data of this is as follows. ^{1 H-NMR δppm (Solvent:} CDCl 3 / 400MHz) 1.76 (s, 6H), 6.89 (s, 1H), 7.25~7.29 (m, 1H), 7.33~7.37
(m, 2H), 7.42-7.46 (m, 2H), 7.87 (dd, 2H), 8.15 (d, 2H)

Synthesis Example 5 Synthesis of N-methyl-N-[(1,1-dimethyl) phenacyl] -2-trifluoromethylbenzamide (Compound No. 1-27) N-[(1,1-dimethyl) phenacyl ] To a mixture of 0.33 g of 2-trifluoromethylbenzamide and 5 ml of tetrahydrofuran was added 38 mg of 60% sodium hydride at room temperature, and the mixture was stirred at the same temperature for 1 hour, then added with 0.28 g of methyl iodide, and reacted at the same temperature for 20 hours. Was. The reaction mixture was poured into water, washed with water, and dried over anhydrous sodium sulfate. The residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (developing solvent: ethyl acetate / n-hexane = 3/7) to obtain 0.30 g of the desired product having a melting point of 149 to 150 ° C. The NMR spectrum data of this is as follows. ¹ H-NMR δppm (Solvent: CDCl ₃ / 400MHz) 1.64 (s, 3H), 1.67 (s, 3H), 2.92 (s, 3H), 6.65 (dd, 1H), 7.40
~ 7.44 (m, 4H), 7.47 ~ 7.49 (m, 1H), 7.59 (dd, 1H), 7.92 (dd,
2H)

Next, typical examples of the compounds of the present invention represented by the above formula (I) are shown in Tables 1 to 4. These compounds can be used in the above synthesis examples or in the various methods for producing the compounds of the present invention. Can be combined based on The abbreviations used in the table are as follows. Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Ph: phenyl group, alll: allyl group

[0085]

Embedded image In the table, 4- [X-1] indicates that X-1 is substituted at the 4-position. The same applies to other descriptions.

[0086]

[Table 1]

[0087]

[Table 2]

[0088]

[Table 3]

[0089]

[Table 4]

[0090]

[Table 5]

[0091]

[Table 6]

[0092]

[Table 7]

[0093]

[Table 8]

[0094]

[Table 9]

[0095]

[Table 10]

Next, test examples will be described. Test Example 1 Effect test on sweet potato nematode After 300 ml of soil of sweet potato nematode contaminated with 7 ml of a drug solution prepared by adjusting the concentration of the compound of the present invention to 1600 ppm,
The drug was mixed so as to be evenly dispersed. After filling the treated soil in a pot (diameter 9 cm, height 8 cm), a two-leaf tomato seedling was transplanted and placed in a greenhouse. Three to four weeks after transplanting the tomatoes, the degree of root knot formation formed on the roots was determined according to the following gall index.

[0097]

[Table 11]

As a result, Compound Nos. 1-1, 1-4, 1-5,
1-17, 1-18, 1-19, 1-24, 1-27, 1-28, 1-31, 1-38, 1-
49, 1-50, 1-51, 1-54, 1-64, 1-65, 1-70, 1-77, 1-8
3, 1-84, 1-93, 1-95, 1-125, 1-126, 1-127, 1-128, 1
-130, 1-131, 1-132, 1-133, 1-134, 1-135, 1-136, 1-
138, 1-139, 1-140, 1-141, 1-142, 1-143, 1-147, 1-1
51, 1-155, 1-156, 1-157, 1-158, 1-159, 1-160, 1-16
1, 1-162, 1-163, 1-164, 1-166, 1-167, 1-168, 1-16
9, 1-171, 1-172, 1-173, 1-174, 1-175, 1-176, 1-17
7, 1-178, 1-179, 1-180, 1-211, 1-212, 1-213 and 2-2
Showed a high control effect with a root-knot index of 1 or less.

Test Example 2 Effect test on oocysts Aimeria tenella field strain was infected and propagated in chicken chicks to obtain fresh immature oocysts, which were sensitized with a solution of the present compound at a predetermined concentration for 10 or 30 minutes, and sensitized. The obtained immature oocysts are centrifuged, the supernatant is removed, a 2% aqueous potassium dichromate solution is added, and sporulation is performed at 25 ° C. for 4 days, whereby a good oocyst control effect is confirmed.

Test Example 3 Effect test on canine filamentous worms The compound of the present invention is orally administered to dogs subcutaneously infected with canine filamentous worms (Dirofilaria immitis). At the time of necropsy 200 days after the infection, by examining the number of parasites produced by the canine filamentous worms in the lungs and heart of the treated animals, a favorable control effect on the canine filamentous worms is confirmed.

Next, preparation examples will be described. Formulation Example 1 (1) 20 parts by weight of the compound of the present invention (2) 72 parts by weight of clay (3) 8 parts by weight of sodium ligninsulfonate The above ingredients are uniformly mixed to prepare a wettable powder.

Formulation Example 2 (1) 5 parts by weight of the compound of the present invention (2) 95 parts by weight of talc The above components are uniformly mixed to give a powder.

Formulation Example 3 (1) 20 parts by weight of the compound of the present invention (2) 20 parts by weight of N, N'-dimethylacetamide (3) 10 parts by weight of polyoxyethylene alkylphenyl ether (4) 50 parts by weight of xylene Are uniformly mixed and dissolved to form an emulsion.

Formulation Example 4 (1) 68 parts by weight of clay (2) 2 parts by weight of sodium ligninsulfonate (3) 5 parts by weight of polyoxyethylene alkylaryl sulfate (4) 25 parts by weight of finely divided silica A mixture of the above components And the compound of the present invention 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) 2 parts by weight of oxylatet polyalkylphenylphosphate-triethanolamine (3) 0.2 parts by weight of silicone (4) 47.8 parts by weight of water Part The above mixture was uniformly mixed and pulverized. Further, (5) 5 parts by weight of sodium polycarboxylate and (6) 42.8 parts by weight of anhydrous sodium sulfate were added, and the mixture was uniformly mixed, granulated, dried, and hydrated. Agent.

Formulation Example 6 (1) 5 parts by weight of the present compound (2) 1 part by weight of polyoxyethylene octyl phenyl ether (3) 0.1 part by weight of polyoxyethylene phosphate (4) 93.9 granular calcium carbonate The parts by weight (1) to (3) are uniformly mixed in advance, diluted with an appropriate amount of acetone, and then sprayed on (4) to remove the acetone to obtain granules.

Formulation Example 7 (1) 2.5 parts by weight of the compound of the present invention (2) 2.5 parts by weight of N-methyl-2-pyrrolidone (3) 95.0 parts by weight of soybean oil Dissolve and disperse a trace amount (ultra l
ow volume formulation).

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A01N 43/40 101 A01N 43/40 101G 101C 43/56 43/56 C C07C 233/81 C07C 233/81 235 / 46 235/46 235/60 235/60 317/32 317/32 317/44 317/44 323/42 323/42 323/62 323/62 C07D 213/64 C07D 213/64 213/82 213/82 231 / 14 231/14

Claims (13)

[Claims] 1. A compound of the formula (I): Wherein A is alkyl, cycloalkyl, phenyl optionally substituted with Y, pyridyl optionally substituted with Y or pyrazolyl optionally substituted with Y,
R ₁ and R ₂ are each alkyl, R ₁ and R ₂ may together form a 3- to 6-membered saturated carbocyclic ring, and R ₃ is a hydrogen atom, alkyl, alkoxyalkyl, alkylthioalkyl or A COR ₄ group, R ₄ is alkyl or alkoxy, X is halogen, alkyl, haloalkyl,
Alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio, alkynylthio,
Haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl optionally substituted with Y, phenoxy optionally substituted with Y, substituted with Y Benzyloxy or pyridyloxy optionally substituted with Y, wherein Y is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylamino Sulfonyl, nitro or cyano, n is an integer of 0 to 5, and when n is 2 or more,
Xs may be the same or different, provided that A is unsubstituted phenyl, R ₁ and R ₂ are each methyl or together form a 6-membered saturated carbocycle, and R ₃ is A hydrogen atom and n is 0], or a salt thereof. 2. X is halogen, alkyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, alkylthio, haloalkylthio, haloalkenylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl , Alkylsulfonyl,
The phenacy according to claim 1, which is haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl optionally substituted with Y, phenoxy optionally substituted with Y or pyridyloxy optionally substituted with Y. Luamine derivatives or salts thereof. 3. X is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano,
The phenacylamine derivative or a salt thereof according to claim 1, which is phenoxy optionally substituted with Y or pyridyloxy optionally substituted with Y. 4. A is phenyl optionally substituted by Y, R ₁ and R ₂ are each alkyl, R ₃ is a hydrogen atom, X is halogen, haloalkyl, haloalkoxy, haloalkylthio, Haloalkylsulfinyl, haloalkylsulfonyl, phenoxy optionally substituted with Y or pyridyloxy optionally substituted with Y, Y is halogen, alkyl, haloalkyl, haloalkoxy or haloalkylthio, and n is 1-3 The phenacylamine derivative or a salt thereof according to claim 1, which is an integer of 5. A compound of the formula (I) Wherein A is alkyl, cycloalkyl, phenyl optionally substituted with Y, pyridyl optionally substituted with Y or pyrazolyl optionally substituted with Y,
R ₁ and R ₂ are each alkyl, R ₁ and R ₂ may together form a 3- to 6-membered saturated carbocyclic ring, and R ₃ is a hydrogen atom, alkyl, alkoxyalkyl, alkylthioalkyl or A COR ₄ group, R ₄ is alkyl or alkoxy, X is halogen, alkyl, haloalkyl,
Alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio, alkynylthio,
Haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylaminosulfonyl, nitro, cyano, phenyl optionally substituted with Y, phenoxy optionally substituted with Y, substituted with Y Benzyloxy or pyridyloxy optionally substituted with Y, wherein Y is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, dialkylamino Sulfonyl, nitro or cyano, n is an integer of 0 to 5, and when n is 2 or more,
Xs may be the same or different, provided that A is unsubstituted phenyl, R ₁ and R ₂ are each methyl or together form a 6-membered saturated carbocycle, and R ₃ is A hydrogen atom, and n is 0, except when n is 0) or a salt thereof,
(1) Formula (II); (Wherein R ₁ , R ₂ , X and n are as described above), and a compound represented by the formula (III): Wherein A is as described above and Z is hydroxy, alkoxy or halogen, or (2) a compound of the formula (I-1); (Where A, R ₁ , R ₂ , X and n are as described above)
And a compound represented by the formula (IV): Wherein R ₃ ′ is an alkyl, alkoxyalkyl, alkylthioalkyl or COR ₄ group, R ₄ is as described above, and W is a halogen. A process for producing the compound of formula (I). 6. A pesticidal composition comprising the phenacylamine derivative of claim 1 or a salt thereof as an active ingredient. 7. An agricultural and horticultural pesticide comprising the phenacylamine derivative or a salt thereof according to claim 1 as an active ingredient. 8. An insecticide, acaricide or nematicide containing the phenacylamine derivative of claim 1 or a salt thereof as an active ingredient. 9. A nematicide containing the phenacylamine derivative of claim 1 or a salt thereof as an active ingredient. 10. An animal parasite control agent comprising the phenacylamine derivative of claim 1 or a salt thereof as an active ingredient. 11. An agent for controlling animal endoparasites, comprising the phenacylamine derivative of claim 1 or a salt thereof as an active ingredient. 12. An agent for controlling an animal disease caused by a parasite, comprising the phenacylamine derivative of claim 1 or a salt thereof as an active ingredient. 13. A method for controlling pests using the amount of the active ingredient of the phenacylamine derivative or a salt thereof according to claim 1.