WO2003086077A1

WO2003086077A1 - Compositions for animal tick or flea control

Info

Publication number: WO2003086077A1
Application number: PCT/JP2003/004836
Authority: WO
Inventors: Sadanori Mizukoshi; Toru Koyanagi; Masayuki Morita; Masashi Imamura
Original assignee: Ishihara Sangyo Kaisha, Ltd.
Priority date: 2002-04-16
Filing date: 2003-04-16
Publication date: 2003-10-23
Also published as: AU2003235186A1

Abstract

Compositions for the control of animal tick or flea, containing as the active ingredient pyrazole compounds represented by the general formula (I) or salt thereof: (I) wherein T is -CH= or nitrogen; R1 is hydrogen, halogeno, alkyl, alkoxy, linear alkoxycarbonyl, or t-butoxycarbonyl; X is oxygen, sulfur, -OCH2CO-, or alkylene; Y is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted 5- or 6-membered heteromonocycle-alkylene, optionally substituted phenyl, optionally substituted pyridyl, or optionally substituted pyrimidinyl; and R3 and R4 are each hydrogen, alkyl, or haloalkyl.

Description

Specification

Composition for controlling ticks or fleas parasitic on animals

"Technical field"

The present invention relates to a composition for controlling ticks or fleas parasitic on animals, which contains a specific pyrazole compound or a salt thereof as an active ingredient.

"Background technology"

Conventionally, various pest control agents and insecticides have been used for fleas parasitic on animals such as livestock, poultry and pets. For example, to control fleas parasitic on pets, pyrethroid insecticides and those based on benzoylphenylperyl insecticides are used.

Most of the specific pyrazole-based compound or a salt thereof which is an active ingredient of the composition of the present invention is described in JP-A-2-966568, JP-A-3-2277975, JP-B-5-4. Known compounds described in, for example, Japanese Patent No. 3700. However, there is no specific description in these documents that specific virazole compounds can control ticks or fleas parasitic on animals. In addition, there is no description that ticks, which are animal parasitic mites, can be controlled.

In general, flea adults are parasitized by mammals and birds, especially pets such as cats, and inhabit by sucking their blood for nutrients. When fleas parasitize pets, irritation and itching can make the pets irritated and cause allergic dermatitis and anemia. It can also transmit a variety of pathogens. In addition, it can be parasitic on the owner, causing redness and rash, which may cause severe itching and allergies such as atopic dermatitis. An object of the present invention is to provide a composition for controlling ectoparasites (anites and fleas) of animals. "Disclosure of the invention"

The present inventors have conducted intensive searches for compounds that can control animal ectoparasites. As a result, they have found that a specific pyrazole compound has a new excellent ectoparasite (mites, fleas) control effect on animals, and completed the present invention. It was also found that certain compounds were novel compounds not described in the literature. That is, the present invention provides a compound represented by the formula (I):

Wherein, T is an CH di- or nitrogen atom, R ¹ is hydrogen atom, a halogen atom, Al kill group, an alkoxy group, an alkylthio group, straight chain alkoxy force Ruponiru group or terpolymers Shah butoxide deer Lupo sulfonyl group, X Is an oxygen atom, a sulfur atom, —OCH ₂ CO— or an alkylene group, Y is an alkyl group optionally substituted with halogen, alkoxy, alkylthio or phenyl; an alkenyl group optionally substituted with halogen; halogen An alkynyl group optionally substituted with alkyl; a cycloalkyl group optionally substituted with alkyl, halogen or cyano; a cycloalkenyl group optionally substituted with alkyl, halogen or cyano;

{Wherein Q is an alkylene group, Cy is a 5- to 6-membered monocyclic heterocyclic group or phenyl group, and R ² is a hydrogen atom; a halogen atom; halogen, cyano, hydroxy, alkoxy or alkoxyl propyl. An alkyl group which may be substituted with halogen; an alkyl group which may be substituted with halogen; an alkylthio group which may be substituted with halogen; a cyano group; a nitro group; an alkoxyl-proponyl group; or it is also good cycloalkyl group substituted with Shiano, j is an integer of 1 ~ 5, j is 2 or more when R ² may be different from each other}; (in the formula, R ² is described above And k is an integer of 1 to 5);

A group represented by the following formula: wherein R ² 'is a hydrogen atom; a halogen atom; an alkyl group substituted with halogen, cyano, hydroxy, alkoxy or alkoxycarbonyl; An alkoxy group optionally substituted with halogen; an alkylthio group optionally substituted with halogen; a cyano group; a nitro group; an alkoxyl-propyl group; an alkylthiol-propyl group or an alkyl, halogen or cyano. A cycloalkyl group; m is an integer of 1 to 4) or

Wherein R ² is as described above, and n is an integer of 1 to ^3, and R ³ and R ⁴ are each independently a hydrogen atom, an alkyl group or a haloalkyl group. A composition for controlling ticks or fleas parasitic on animals, comprising the pyrazole-based compound represented by the formula or a salt thereof as an active ingredient, and a ticks or fleas parasitic on animals using an effective amount of the compound of the formula (I). And a method for controlling pests.

Further, the present invention provides a compound of the formula (I ′):

[Wherein T is one CH = is a nitrogen atom, R ¹ ′ is an alkoxy group or an alkylthio group, X is an oxygen atom, a sulfur atom, 〇CH ₂ CO— or an alkylene group, "Is a hydrogen atom; a halogen atom; an alkyl group substituted with a halogen, cyano, hydroxy, alkoxy or alkoxy group; an alkoxy group optionally substituted with a halogen; an alkylthio group optionally substituted with a halogen; a cyano group A nitro group; an alkoxyl group; an alkylthio group or a cycloalkyl group which may be substituted with alkyl, halogen or cyano, m is an integer of 1 to 4, and R ³ and R ⁴ are each independently A hydrogen atom, an alkyl group or an octaalkyl group] or a salt thereof, and a compound represented by the formula (I "):

[Wherein T is one CH = or a nitrogen atom, and R ¹ is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, a straight-chain alkoxyl ponyl group, or a Yuichi Sharybutoxycarponyl group, X ′ is an alkylene group; R ² is a hydrogen atom; a halogen atom; an alkyl group optionally substituted with halogen, cyano, hydroxy, alkoxy or alkoxycarbonyl; an alkoxy group optionally substituted with halogen; An alkylthio group which may be substituted; a cyano group; a nitro group; an alkoxyl group; an alkylthio group or a cycloalkyl group which may be substituted with alkyl, halogen or cyano, and k is an integer of 1 to 5; Table with a number, R ³ and R ⁴ are each independently a hydrogen atom, an alkyl group or a haloalkyl group} It is the pyrazole - le compound or a salt thereof.

The salt of the pyrazole compound is a salt of the pyrazole compound and an acidic substance, for example, an acid such as hydrochloric acid, sulfuric acid, or carbonic acid, and these can be produced by a conventional method. The compound of formula (I) may exist in E-form or Z-isomer depending on the C = N bond of the imino moiety. This geometric isomer is formed as a single substance or a mixed substance depending on the method for producing the compound of the formula (I) or its production process. Further, the compound of the formula (I) has an asymmetric carbon atom depending on the selection of each substituent, and thus may have an optical isomer.

Examples of the alkyl group or alkyl moiety in the formula include those having 1 to 6 carbon atoms, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, etc., which have a linear or branched aliphatic chain structure. Methyl, ethyl, propyl, and butyl are preferred, including isomers.

Examples of the alkylene group include those having 1 to 6 carbon atoms, such as methylene, ethylene, propylene, butylene, pentylene, and hexylene.

The alkenyl group or alkenyl moiety generally has 2 to 6 carbon atoms, for example, vinyl, probenyl, butenyl, pentenyl, hexenyl, etc., which have a linear or branched fatty chain structure. Although it includes isomers, propenyl or butenyl is preferred.

The alkynyl group or alkynyl moiety generally has 2 to 6 carbon atoms, for example, Examples include ethynyl, propynyl, butynyl, pentynyl, hexynyl and the like, including those having a structural isomer of a linear or branched aliphatic chain, but propynyl and butynyl are preferred.

Examples of the cycloalkyl group include those having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Examples of the cycloalkenyl group include those having 5 to 6 carbon atoms, such as cyclopentenyl and cyclohexenyl.

Examples of the halogen thickener or halogen include fluorine, chlorine, bromine, and iodine.

When each substituent in the formula has a secondary substituent, the number of secondary substituents is 1 to 2 or more, and when it is 2 or more, the secondary substituents are the same or different. You can. When these contain an alkyl moiety, examples of the alkyl moiety include those having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, and hexyl. In addition, methyl, ethyl, propyl, and butyl are preferable, including those having structural isomers of fatty chains.

Examples of the 5- to 6-membered monocyclic heterocyclic group represented by Cy include pyrrolyl, pyrrolinyl, pyrrolidinyl, furanyl, dihydrofuranyl, tetrahydrofuranyl, phenyl, dihydrothenyl, tetrahydrothenyl, pyrazolyl, 'birazolinyl, Pyrazolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxazolyl, isoxazolinyl, isoxazolidinyl, thiazolyl, thiazolinyl, thiazolinyl, isothiazolinyl, isothiazolinyl, isothiazolinyl, isothiazolinyl , Oxadiazolidinyl, thiadiazolyl, thiadiazolinyl, thiadiazolidinyl, triazolyl, triazolinyl, triazolidinyl, tet Zolyl, tetrazolinyl, tetrazolidinyl, dioxolyl, dioxolanyl, dithiolyl, dithiolanyl, pyridyl, dihydropyridyl, tetrahydropyridyl, piperidinyl, pyrimidyl, dihydropyrimidyl, tetrahydropyrimidyl, hexahydropyrimidyl, pyridazinyl, dihydro Pyridazinyl, tetrahydro Examples include pyridazinyl, hexahydropyridazinyl, pyrazinyl, dihydropyrazinyl, tetrahydrovirazinyl, piperazinyl, pyranyl, dihydroviranyl, tetrahydropyranyl, dioxinyl, dioxenyl, dioxanyl, dithianil, and morpholinyl. Of these, pyridyl, pyrimidinyl, pyridanyl, dioxolanyl, dithiolanyl, chenyl, and furanyl are preferred. The compound of the formula (I) or a salt thereof can be produced, for example, by the following method. Further, among the compounds of the formula (I), the compound of the formula () and the compound of the formula (Γ ′) are novel compounds.

(X, Y, T, RR ³ and R ⁴ are as described above, A is _CH = N0H group or -CHO group, B is a halogen atom or -CHO group, B is a halogen atom or -0N¾ a group, provided that, a is - CH = N0H group B is a halogen atom, a is - CH0 groups B - is 0 nH ₂ group)

(i) Production method (when A is -CH = N0H group and B is a halogen atom):

This reaction is usually carried out in the presence of a base and a solvent, and examples of the base include alkali metal hydrides such as sodium hydride and lithium hydride; alkalis such as sodium hydroxide and potassium hydroxide. Metal hydroxides; alkali metal carbonates such as sodium carbonate and lium carbonate; triethylamine, pyridine, organic bases such as 1,8-diazavic mouth [5.4.0] _7_ndecene Examples of the solvent include aprotic polar solvents such as dimethylformamide and hexamethylphosphoric triamide; ethers such as tetrahydrofuran and dioxane; and the reaction temperature is usually 0 to 100, preferably It is 10 to 60 ° C, and the reaction time is usually 0.5 to 12 hours, preferably 1 to 4 hours.

(ii) Production method (when A is -CH0 group and B is -0N¾ group):

This reaction is usually carried out in the presence of a solvent, such as methanol or ethanol. Alcohols such as ethanol and isopropanol; ethers such as tetrahydrofuran and dioxane; halogenated hydrocarbons such as methylene chloride and chloroform; aprotic electrodes such as dimethylformamide and hexamethylphosphoric triamide The reaction temperature is usually from 0 ° C to reflux temperature, preferably from 20 to 80 ° C, and the reaction time is usually from 0.5 to 6 hours, preferably from 1 to 4 hours. is there . In the above production method, the compound represented by the formula (II) can be produced, for example, by the following method. It can also be produced by the method described in JP-A-3-227975 or JP-B-5-43700.

[Ii] when X is an oxygen atom or —0C¾CO— group;

It can be produced via the following reaction steps [A] and [B], or via reaction steps [A], [B] and [C], respectively.

Reaction step (A)

(R ³ and R ⁴ are as described above, X ¹ is an oxygen atom or a —0CH ₂ C0— group, W is a halogen atom or a Hato C¾CO group (Hal is a halogen atom), Y is as described above 1

The above reaction is usually performed in the presence of a base and a solvent. Examples of the base include alkali metal hydrides such as sodium hydride and lithium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; n-butyllithium, tert-butyllithium Alkyl lithium; organic bases such as triethylamine, pyridine, and 1,8-diazabicyclo [5.4.0] -7-ndecene; and non-public solvents such as dimethylformamide and hexamethylphosphoric triamide as solvents. Polar solvents; ethers such as tetrahydrofuran and dioxane. The reaction temperature of the above reaction is usually 50 to 150 ° (: preferably 70 to 120 ° C, and the reaction time is usually 2 to 24 hours, preferably 4 to 10 hours. is there Reaction step (B)

(R ³ , RX ¹ and Y are as described above)

The above reaction is usually performed in the presence of a solvent. Examples of the solvent include aprotic polar solvents such as dimethylformamide and hexamethylphosphoric triamide; and ethers such as tetrahydrofuran and dioxane. The reaction temperature of the above reaction is usually 0 to 100 ° C, preferably 10 to 80 ° C, and the reaction time is usually 1 to 6 hours, preferably 1.5 to 4 hours.

Reaction step (C)

[The mineral of the _{NH 2 0H (Mineral ac id sal} t of NH 2 OH), include hydrochlorides or ^{^{sulfates, R 3, R 4, X}} 1 and Y are as defined above]

The above reaction is usually performed in the presence of a base and a solvent. Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and lithium carbonate, and triethylamine, organic bases such as pyridine, and the like. Examples of the solvent include alcohols such as methanol and ethanol; ethers such as tetrahydrofuran and dioxane; aprotic polar solvents such as acetate nitrile and dimethylformamide; and water. These can be used alone or as a mixture. The reaction temperature of the above reaction is usually 0 to 80 ° C, preferably 10 to 60 ° C, and the reaction time is usually 0.5 to 12 hours, preferably 1 to 6 hours.

(Mouth) when X is a sulfur atom; It can be produced via the following reaction step [D] or via reaction steps [D] and [E].

Reaction step (D)

(R ³ , R ⁴ , Y and Hal are as described above)

The above reaction is usually performed in the presence of a base and a solvent. As the base and the solvent, those similar to those in the above-mentioned reaction step [A] can be used. In addition, the reaction temperature of the above reaction is usually 110 to 150 ° C, preferably 0 to 100 ° C, and the reaction time is usually 0.5 to 24 hours, preferably 1 to 12 hours. It is.

Reaction step (E)

(R ³ , R ⁴ and Y are as described above)

In the above reaction, the reaction conditions such as the mineral acid salt of N¾OH (Mineral acid salt of NH ₂ OH), the base and the solvent, and the reaction temperature and the reaction time are the same as those in the reaction step (C). .

(8) X is an oxygen atom and Y is Y ¹ (Y ^] is an alkyl group, an alkenyl group or an alkynyl group,

(Where Q, Cy, R ² and j are as described above).

In the above case, in addition to the above-mentioned case (a), it can also be produced via the following reaction step [F] or via the reaction step [G].

Reaction step (F)

(R ³ , R ⁴ , Y ¹ and Hal are as described above)

In the above reaction, the base and solvent used, and the reaction conditions such as the reaction temperature and the reaction time are the same as those in the above reaction step [D].

Reaction step (G)

(R ³ , R ⁴ and Y ¹ are as described above)

In the above reaction, the reaction conditions such as the mineral acid salt of N¾OH (Mineral acid salt of NH ₂ OH), the base and the solvent, and the reaction temperature and the reaction time are the same as those in the reaction step (C). . In the above-mentioned production method, the halogen atom represented by B, W and Hal includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

The compound of the formula (I) is effective for controlling ticks or fleas that inhabit the body surface of a host animal, but is particularly effective in controlling ticks, fleas and cat fleas. Mites or fleas infest in the host animal's back, armpits, lower abdomen, and inner thighs. There are many types of mites or fleas, and it is difficult to list them all.

Examples of animal parasite mites include B. ticks (Boophi lus microplus), R. sylvestris (Rhipicephalus sanguineus), Ixodid ticks (Haem ap ysal is longicornis), Haemap ysal is f lava, and Hagripane emasima is Haemaphysal is cone inn a, Haemaphysal is japonica, Haemaph ysal is kitaokai, Haemaphysal is ias, Ides pons, ema, odes ova, ema Tick (I Dermanyssus galus (Dermanyssus gallinae); Dermanyssus gallinae; ); Trichoderma mites (Eutrombicula wic manni), Akatsugamushi (Leptotrombidium akamushi), Futteggamushi (Leptotromb idium pallidum), Leptotrombidium fun, Tosatsugamushi

(Le totrombidium tosa), European locust (Neotrombicula autumnal is), American stag beetle (Eutrombicula alfreddugesi), Miyagawa evening matsgamushi (Helenicula miyagawai), etc .; The cat mite

ッ (Cheyletiella blakei); メギゥ (Psoropt es cuniculi), ゥゥ (Chorioptes bovis), ゼンミ

(Otodectes cynotis), Scaroptes scabiei, and Scaropteridae (Notoedres cati); and Pimples (Demo dex canis). The compound of the formula (I) is suitable for controlling the above-mentioned ticks among animal parasitic mites.

The fleas include, for example, ectoparasitic wingless insects belonging to the order Flea (Siphonaptera), specifically, fleas belonging to the family Flea (Pulicidae), the family Flea (Ceratephyllus), and the like. Fleas belonging to the family Fleas include fleas

(Ctenocephalides canis), Cat flea (Ctenocephalides felis), Human flea (Pulex irritans), Niftrif flea (Ec idnop aga gallinacea), Capes nes, Fleas (Xenopsylla cheopis, Leptops ssia, Leptopssyla, Leptopssylla, Europe) And the flea of the family Flea family, especially the flea and flea of the flea family, and the compound of formula (I) is effective.

Host animals for which the compounds of formula (I) are effective include dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, egrets, ferrets, birds (eg, pigeons, birds). Pets, poultry such as horses, poultry, pigs, and sheep; and poultry such as ducks and chickens. Among these, the compound of the present invention is effective for mites or fleas parasitic on pets or domestic animals. It is particularly effective on dogs and cats among pet animals, and is especially effective on domestic animals and cats in livestock.

When the compound of the formula (I) is used as an animal mite or fleas control agent, it may be used as it is, and powders, granules, tablets, powders, capsules, liquids, emulsions, It can also be used after being formulated into various forms such as an aqueous suspension and an oil suspension. In addition, other than the above-mentioned preparation form, any preparation form commonly used in this field can be used as long as the object of the present invention is satisfied. Auxiliary agents used in the formulation include anionic surfactants and nonionic surfactants exemplified as auxiliary agents for agricultural chemicals described later; cationic surfactants such as cetyltrimethylammonium bromide. Activator: water, acetone, acetonitrile, monomethylacetamide, dimethylacetamide, dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol , Propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol normal monoethyl ether Solvents such as ter, diethylene glycol butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; such as butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium metabisulfite, propyl gallate, sodium thiosulfate Antioxidant

Film-forming agents such as polyvinylpyrrolidone, polyvinyl alcohol, copolymers of vinyl acetate and vinylpyrrolidone; vegetable oils and mineral oils exemplified as auxiliary agents for the formulation of agricultural chemicals described below; lactose, sucrose, glucose, starch, wheat flour, corn flour And soybean oil cake, defatted rice bran, calcium carbonate, and other carriers such as commercially available feed materials. Each component of these adjuvants may be used alone or in combination of two or more without departing from the purpose of the present invention. More than one species can be appropriately selected and used. In addition to the above-mentioned adjuvants, they can be appropriately selected from those known in the art, and can be appropriately selected from various adjuvants used in the agrochemical field described below. You can also.

The compounding ratio of the compound of the formula (I) and various auxiliaries is usually about 0.1: 99.9 to 90:10. In actual use of these preparations, they can be used as they are, or diluted to a predetermined concentration with a diluent such as water, and added with various spreading agents (surfactant, vegetable oil, mineral oil, etc.) as necessary. Can be used.

Compounds of formula (I) may be mixed with various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, fragrances, preservatives, etc. Or they can be used in combination. Also, if necessary, mix or use in combination with other animal and agricultural chemicals, such as anthelmintics, anticoccidials, insecticides, acaricides, fleasicides, nematicides, fungicides, antibacterials, etc. In this case, a better effect may be exhibited.

Administration of the compound of formula (I) to a host animal is effected orally or parenterally. Examples of the oral administration method include a method of administering a tablet, a liquid preparation, a capsule preparation, a wafer, a biscuit, minced meat, and other feeds containing the compound of the formula (I). Parenteral administration includes, for example, preparing a compound of formula (I) into an appropriate formulation and then injecting it into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; (Spot-on) treatment, pour-on treatment, spray treatment, etc .; administration to the body surface; embedding a resin piece containing the compound of formula (I) under the skin of a host animal; Can be

The dose of the compound of the formula (I) to the host animal varies depending on the administration method, purpose of administration, disease symptoms and the like, but is usually 0.1 mg / LOO g to 1 kg body weight of the host animal, preferably LOO g. It is appropriate to administer at a rate of 0.1 mg to 10 g.

The compound of the formula (（) and the compound of the formula (Γ ′) are also useful as an active ingredient of an agricultural chemical such as an insecticide, an acaricide, a nematicide, a soil insecticide, and a fungicide. These compounds include, for example, Nami-Nami, Nisenami-Nami, Kanza-Nami, Mika Plant-parasitic mites such as red mite, apple spider mite, cyanopodidae, citrus abaloneii, spider mite; aphids such as peach aphid, 、ァブラ、、、コココココ, Gypsy moth, Kobnomameiga, Anthracidae, Colora dohamushi, Periham beetle, Poleui building, Scarabaeidae, Leafhopper, Beetle, Stinkbugs, Whiteflies, Azamazuma, Bats, Butterfly Agricultural pests such as Tamana-yaga, Hiragura-aga, Araris, etc .; such as root-knot nematodes, cysts-centres, negusarecenti-yus, rice-singarecenti-yu, strawberry-medium-citrus, matsunoza-centiyu, etc. plant Gastropods such as slugs, scabies, etc .; soil pests such as isopods such as dung beetles and wallworms; sanitary pests such as house dust mites, cockroaches, house flies and scallops; Stored pests such as Azukizushi beetles, skull beetles, worms, and worms; garlic, house harmful insects such as swords, bark beetles, and termites; indoor dust mites such as mites mites, mites mites It is effective in controlling pests. Above all, it is effective for controlling agricultural pests and plant parasitic nematodes. It is also effective in controlling various pests that are resistant to chemicals such as organophosphates, carbamates, and synthetic pyrethroids. Furthermore, because of its excellent systemic translocation, the active ingredient can be applied to the soil to control soil harmful insects, mites, nematodes, gastropods, and isopods, and at the same time as foliage. Pests can also be controlled. Furthermore, these compounds are also effective in controlling diseases such as powdery mildew and downy mildew.

The compound of the formula (Γ) and the compound of the formula (Γ ′) are mixed with various agricultural auxiliaries to prepare powders, granules, water dispersible granules, wettable powders, aqueous suspensions, oil suspensions. It can be formulated and used in various forms such as water solvents, emulsions, liquids, pastes, aerosols, and micro-sprays. As an auxiliary, solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, a mixture of kaolinite and sericite, clay, sodium carbonate, baking soda, sodium sulfate, zeolite, silica, starch, and the like; Water, toluene, xylene, solvent naphtha, dioxane, Solvents such as acetone, isophorone, methyl isobutyl ketone, cyclobenzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, alcohol, and methylcellosolve; fatty acid salts, benzoic acid Salt, alkyl sulfosuccinate, dialkyl sulfosuccinate, polycarboxylate, alkyl sulfate, alkyl sulfate, alkyl aryl sulfate, alkyl diglycol ether sulfate, alcohol sulfate, alkyl sulfonate, alkyl sulfa Reel sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonic acid salt, polystyrene sulfonate, alkyl phosphate ester salt, alkyl aryl phosphate Styryl aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl sulfate, polyoxyethylene alkyl aryl sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl Anionic surfactants and spreading agents such as aryl phosphate salts and salts of formalin condensate of naphthalene sulfonic acid; sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides, fatty acid alcohol polydaricol ethers, acetylene Glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene Polystyrene glycol ether, polyoxyshethylene glycol alkyl ether, polyethylene glycol, polyoxyethylene fatty acid ester, polyoxyethylene sorbin fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, poly Nonionic surfactants and spreading agents such as oxypropylene fatty acid esters; olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil Vegetable oils such as soybean oil, rapeseed oil, linseed oil, cutting oil, and liquid paraffin, and mineral oils. These auxiliaries can be selected from those known in the art. In addition, various commonly used auxiliaries such as bulking agents, thickeners, anti-settling agents, anti-freezing agents, dispersion stabilizers, safeners, and fungicides can be used. You. The compounding ratio of the compound of the above formula (Γ) or the formula (Γ ′) and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10. When these preparations are actually used, they can be used as they are, or can be diluted with a diluent such as water to a predetermined concentration, and added with various spreading agents as necessary.

The application rate cannot be specified unconditionally due to differences in weather conditions, formulation, application time, application place, type of pest or occurrence, etc., but it is generally performed at an active ingredient concentration of 0.05 to 800 000 ΠΙ, preferably 0.5 to 500 000 ρρπι. The application rate per unit area is 0.05 to 50,000 g, preferably 1 to 30,000 g of the compound of the formula (Γ) or the formula (Γ ′) per hectare.

The method of application is to apply the preparation or a dilution thereof in a usual manner, ie, spraying (for example, spraying, spraying, misting, atomizing, spraying, water surface application, etc.), soil application (mixing, irrigation, etc.), It can be performed by surface application (coating, dressing, coating, etc.), immersion poison bait, etc. It can also be applied by the so-called ultra-low concentration small volume application method (ultra low volum e). In this method, it is possible to contain 100% of the active ingredient.

Some preferred embodiments of the compound as an active ingredient of the composition for controlling parasites (anites, fleas) of animals related to the present invention are illustrated below, but the present invention is not limited thereto. In addition, a compound in which the definitions of the substituents described in (1) to (3), (4) to (8), and (9) are mutually combined is also included in a desirable compound mode. Further, the compound represented by the formula (Γ '') described in (14) below can be produced by the same method as the compound of the formula (I).

(1) The compound of the formula (I) wherein X is an oxygen atom, a sulfur atom or an alkylene group.

(2) The compound of the formula (I) wherein X is an oxygen atom.

(3) The compound of the formula (I) wherein X is an alkylene group.

(4) Υ is an alkyl group optionally substituted with halogen, alkoxy, alkylthio or phenyl; an alkenyl group optionally substituted with halogen; an alkynyl group optionally substituted with halogen; an alkyl group optionally substituted with alkyl, halogen or cyano. A cycloalkyl group; (Wherein R ² and k are as described above);

(Wherein, R ² ′ and m are as described above) or

A compound of formula (I) which is a group wherein R ² and n are as defined above.

(5) Y is an alkyl group optionally substituted with halogen, alkoxy, alkylthio or phenyl; an alkenyl group optionally substituted with halogen; an alkynyl group optionally substituted with halogen, or an alkyl group optionally substituted with alkyl, halogen or cyano. The compound of (4), which is also a cycloalkyl group.

(6) Y

Le

Group (wherein R ² and k are as described above);

A group (wherein, R ² ′ and m are as described above); or

(Wherein R ² and n are as defined above).

{Wherein Q, Cy, R ² and] are as defined above}.

(8) The compound according to (7), wherein Cy is a pyridyl group, a dioxolar group, a cyenyl group, a furanyl group or a phenyl group.

(9) T is --CH =, and R ¹ is a 4-butoxycarbonyl group at position 4. Certain compounds of formula (I).

(10) The compound represented by the formula (I ′).

(11) T is -CH =; R ¹ 'is an alkoxy group; X is an oxygen atom; R ² ' is a halogen atom; and R ³ and R ⁴ are both alkyl groups. I

') Compound.

(12) A compound represented by the formula (Γ ′).

(13) The compound of the formula (Γ ′), wherein T is —CH =; R ¹ is a tertiary butoxycarbonyl group; and R ³ and R ⁴ are both alkyl groups.

(14) Equation (I ','):

Wherein, T is an CH di- or nitrogen atom, C0 ₂ Am) is a tertiary amyl Karuponiru group, X is an oxygen atom, a sulfur atom, One OCH ₂ CO- or alkylene down group, Y ' Is an alkyl group optionally substituted by halogen, alkoxy, alkylthio or phenyl; an alkenyl group optionally substituted by halogen; an alkynyl group optionally substituted by halogen; substituted by alkyl, halogen or cyano A cycloalkyl group which may be substituted with alkyl, halogen or cyano; a cycloalkenyl group;

{Wherein Q is an alkylene group, Cy is a 5- to 6-membered monocyclic heterocyclic group or phenyl group, and R ² is a hydrogen atom; a halogen atom; substituted with halogen, cyano, hydroxy, alkoxy or alkoxycarbonyl. An alkyl group which may be substituted; an alkoxy group which may be substituted with halogen; an alkylthio group which may be substituted with halogen; a cyano group; a nitro group; an alkoxycarbonyl group; an alkylthio group or an alkylthio group substituted with alkyl, halogen or cyano. Or a cycloalkyl group, and j is an integer of 1 to 5; (In the formula, R ² is as described above, and k is an integer of 1 to 5.)

(Wherein, R2 is as defined above, n represents an integer of 1 to 3) Birazo that is, represented by R ³ and R ⁴ are each independently a hydrogen atom, an alkyl group or a haloalkyl group - Compounds.

(15) Y ′ is an alkyl group optionally substituted with halogen, alkoxy, alkylthio or phenyl; an alkenyl group optionally substituted with halogen; an alkynyl group optionally substituted with halogen; substituted with alkyl, halogen or cyano (14) The compound according to (14), which is a cycloalkyl group or a cycloalkenyl group which may be substituted with alkyl, halogen or cyano.

Next, some preferred embodiments of the method for controlling ticks or fleas parasitic on animals according to the present invention will be exemplified below, but the present invention is not limited thereto.

(16) A method for controlling ticks or fleas parasitic on animals, comprising using an effective amount of the compound of the formula (I) or a salt thereof.

(17) The method of (16) for controlling ticks on animals.

(18) The method according to (17), wherein the mite is a tick.

(19) The tick is a red tick, a red tick, a red tick, a red tick, a red tick, a red tick, a red tick, a red tick, a red tick, a red tick, a red tick, a red tick, a red tick, a red tick, or a red tick.

(20) The method according to (18), wherein the ticks are Acarina ticks, Acarina ticks, Acarina ticks, Acarina ticks, Acarina ticks, Schulze ticks, Amino ticks, or Acarina ticks.

(21) The method according to (18), wherein the ticks are Haemaphysalis longicornis.

(22) The method of (16) for controlling fleas parasitic on animals.

(23) The method according to (22), wherein the flea is a flea belonging to the family Flealaceae or the Family Fleaceae. (24) The method according to (22), wherein the fleas are fleas belonging to the family Flea.

(25) The method according to (24), wherein the fleas belonging to the family Flea are fleas, fleas, fleas, nymphs, capps flea, flea flea, European flea or flea flea.

(26) The method according to (24), wherein the fleas belonging to the family Flea are fleas or cat fleas.

(27) The method according to (16), wherein the animal is a domestic animal or a companion animal.

(28) The method according to (27), wherein the animal is a pet animal.

(29) The method according to (28), wherein the companion animal is a dog, cat, mouse, rat, hamster, guinea pig, ris, peacock, ferret, pigeon, worm, mysterious bird, fowl, parakeet, zinus pine or canary.

(30) The method according to (28), wherein the pet animal is a dog or cat.

(31) The method according to (27), wherein the livestock is a peas or peas.

In order to describe the present invention in more detail, examples will be described below, but these do not limit the present invention.

[Synthesis Example 1] Synthesis of 4-tert-butoxy {1,3-dimethyl-5- (5-bromo-2-pyridyloxy) -pyrazole-4-yl} methyleneaminooxymethylpentene (Compound No. 31)

JP-A-2-96568 Synthesis Example 1 0.95 g of 4-hydroxyiminomethyl-1,3-dimethyl-5- (5-promo-1-pyridyloxy) -vinyl sol produced according to (1)-(2) After dissolving in 15 ml of N, N-dimethylformamide, 0.135 g of sodium hydride (60% nudiol mixture) was gradually added under ice-cooling. After the addition, stirring was continued at room temperature. After confirming that the generation of hydrogen gas had ceased, 5 ml of a solution of 4 g of tert-butoxybenzyl bromide in 1 g of N, N-dimethylformamide was added dropwise. After the reaction, the reaction solution was poured into ice water to stop the reaction. Next, ethyl acetate was added for extraction, and the organic layer was washed with water and saturated saline, and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was Column chromatography. The objective was purified (eluent Kisan'no acetate Echiru = 2 Bruno 1 to n-) (.. Compound N o 3 1; refractive index _{^{^{n D 1 8 '5 1 5}}} 8 6) 1 O lg I got

[Synthesis Example 2] Synthesis of 0- (4-ί-butoxycarbonyl benzyl) -5- (4-chlorobenzyl) -1,3-dimethyl-4-pyrazolecarbaldehyde oxime (Compound No. 59)

(1) 7.5 ml of ^ butyllithium was gradually added dropwise at _78 ° C to a mixed solution consisting of 80 ml of tetrahydrofuran and 5 ml of hexamethylphosphoric acid triamide containing 4 g of ethyl 3,3-dimethyl-4-pyrazolecarboxylate. Stirring was continued at the temperature for 20 minutes. Next, while maintaining the temperature, a solution of 4.9 g of 4-chlorobenzylbenzene in 10 ml of tetrahydrofuran was added dropwise, and the mixture was stirred for 30 minutes, and the reaction was continued for 1 hour while gradually returning to room temperature. After completion of the reaction, the reaction solution was poured into ice water, extracted with ethyl acetate, the organic layer was washed with water and saturated saline, and then dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (hexane / ethyl acetate = 2/1) to give 5-

1-3.5 g (4-ethyl benzyl) -1,3-dimethyl-4-pyrazolecarboxylate;

(2) To a solution of 0.3 g of lithium aluminum hydride suspended in 100 ml of ether, slowly add a solution of 3.4 g of the carboxylic acid ester obtained in (1) in 10 ml of ether, and then at room temperature for 1 hour, The reaction was performed for 3 hours under heating and reflux. After completion of the reaction, the solution was cooled to room temperature, 0.6 ml of water and 0.5 ml of a 10% aqueous sodium hydroxide solution were added, and the mixture was stirred at room temperature. The insoluble material was filtered off, and the filtrate was dried over anhydrous sodium sulfate. And dried. After evaporating the solvent, 1. lg of 5- (4-chlorobenzyl) -1,3-dimethyl-4-pyrazolylmethyl alcohol was obtained.

(3) To a solution of 1.05 g of the pyrazolylmethyl alcohol obtained in (2) in 40 ml of methylene chloride, 1.36 g of pyridinum chromate chromate was gradually added at room temperature, and the mixture was further stirred for 30 minutes. After completion of the reaction, 100 ml of ether was added and the insolubles were filtered off. The filtrate was purified by silica gel column chromatography (hexane / ethyl acetate = 2/1) to give 5-

0.6 g of (4-chloro mouth benzyl) -1,3-dimethyl-4-pyrazolcarbaldehyde was obtained. (4) A solution of 0.57 g of the catalyzed rubaldehyde obtained in (3) and 0.51 g of 0 to (4-butoxycarbonyl benzyl) -hydroxylamine in 10 ml of methanol was heated to reflux for 1.5 hours. After completion of the reaction, methanol was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane / ethyl acetate = 2/1) to obtain the target compound ^

(4 - Bok butoxide deer Lupo benzyl) -5- (4-black port benzyl) - 1, 3 - dimethyl - 4 - pyrazole carbaldehyde O oxime (Compound No. 59; refractive index _{^{^{n D 17 '8 1. 5445)}}} 0.54 g was obtained.

Table 1 below shows typical examples of the compound of the above formula (I). These compounds are produced according to the descriptions in the above Synthesis Examples and Synthesis Examples 1 to 3 of JP-A-2-96568. No. in each table represents the compound number; X, Y, T, R ¹ , R ³ and R ⁴ represent each substituent in the formula (I); Bu (t) represents a tertiary butyl group And Am (t) represents a tertiary amyl group. Further, the substitution position in the pyridyl group, pyrimidinyl group and pyridazinyl group in the substituent represented by Y is defined as follows for convenience, with the bonding position being 1 (Ar is a pyridyl group, pyrimidinyl group or pyridazinyl group). Represents a group).

Furthermore, the eta _eta ^iota according as a physical property representing the refractive index at t ° C.

Continued

XYTR ¹ R ³ R ⁴ Physical properties

0 4- CF ₃ - 6 - C Bok 2 - Pirishi "Le _{-CH = 4-C0 2 Bu (} t) CH 3 c¾ n D 33 - 0 1. 5164

0 3 -Methoxy-2-pyridyl-CH = 4-C0 ₂ Bu (t) CH ₃ CH ₃

0 3-Trifluoro D-methoxy- -CH = 4-C0 ₂ Bu (t) CH ₃ CH ₃

2—Pirishi ', Le

0 4 12 trough 2-Pisyl "-4-C0 ₂ Bu (t) CH ₃ CH ₃

0 3 -Recho, Trifolo- -CH = 4-C0 ₂ Bu (t) CH ₃ CH ₃

2-Pili ,, Le

0 4-C1- -CH = 4-C0 ₂ Bu (t) CH ₃ CH ₃

2,6-pyriminyl

0 4-CF ₃ --CH = 4-C0 ₂ Bu (t) CH ₃ CH ₃

2, 6—pyrimici "nil

0 3-C1- -CH = 4-C0 ₂ Bu (t) CH ₃ CH ₃

2, 4-pyrimici "nil

0 4-CH ₃ --CH = 4-C0 ₂ Bu (t) CH ₃ CH ₃

2,6-pyriminyl

0 2-Pyryl 3-N 4-CI CH ₃ CH ₃ Melting point 98 ~ 99

0 2 - Pirishi ,, le _{_{3-NH CH 3 c¾ n D}} 26 - ° 1. 5768

0 2—Piricil 2 -NH CH ₃ c¾ n _D ²⁶ '. 1. 5462

0 2—Pyridyl 2-N 4-C0 ₂ Bu (t) CH ₃ CH ₃

0 -CH (CF ₃ ) CH ₃ 2-N 4-C0 ₂ Bu (t) C¾ CH ₃ Continued

Continuation of Table 1

No. XYTR ¹ R ³ R 4 Physical properties

76 0 -CH (CH ₃ ) -C≡CH -CH = 4-C0 ₂ Am (t) c¾ CH ₃

77 0 -CH ₂ CH ₂ OC¾CH -CH = 4-C0 ₂ Am (t) CH ₃ CH ₃

78 0 2 -Chenylmethyl -CH = 4-C0 ₂ Am (t) CH ₃ CH ₃

79 0 3-C1- -CH = 4-C0 ₂ Am (t) CH ₃ CH ₃

2, 4-Ipirimici'nil

80 0 4-CH ₃ --CH = 4-C0 ₂ Am (t) CH ₃ CH ₃

2, 6-pyriminyl

81 0 2 -Pirishi ', methyl -CH = 4-C0 ₂ Am (t) CH ₃ C¾

82 0 2 -Fura :: Rmethyl -CH = 4-C0 ₂ Am (t) c¾ CH ₃

83 0 3-F-2_Piricyl -CH = 4-C0 ₂ Am (t) CH ₃ c¾

84 0 4 1 Br-2-pyridyl -CH = 4-C0 ₂ Am (t) CH ₃ CH ₃

85 0 4— C¾-2 -Piricyl -CH = 4-C0 ₂ Am (t) CH ₃ CH ₃

86 0 4- CF ₃ - 2 - Pirishi ', Le _{-CH = 4-C0 2 Am (} t) CH 3 c¾

87 0 2—Pirishiyl -CH = 4-C0 ₂ Am (t) CH ₃ CH ₃

88 s 2—Pili ,, -CH = 4-C0 ₂ Am (t) CH ₃ C¾

89 0 4,6 -Cycopene-2-pyridyl -CH = 4-C0 ₂ Am (t) c¾ CH ₃

90 0 4-Cyan-2-pyrri ,, -CH = 4-C0 ₂ Am (t) CH ₃ CH ₃

91 0 3-Methylthio-1-pyridyl -CH = 4-C0 ₂ Am (t) CH ₃ CH ₃

92 0 4-C0 ₂ CH ₃ -2-k ° Ris', -CH = 4-C0 ₂ Am (t) CH ₃ c¾

_{93 0 4- CF 3 - 6- C} 2- Pirishi "Le _{-CH = 4-C0 2 Am (} t) CH 3 CH 3

94 0 3 -Methoxy-2-pyridyl -CH = 4-C0 ₂ Am (t) CH ₃ CH ₃

95 0 4 12 trough 2 -Pirishi ', le -CH = 4-C0 ₂ Am (t) CH ₃ c¾ Test Example 1: Effect test on flea adults by the dry film method test 0.5 ml of acetone solution of the test compound at a predetermined concentration (6 concentrations, common ratio 2.5) was placed in a glass tube with a smooth bottom (2.6 cm inside diameter, bottom area 5. 3 cm ^2, dispensed height 12cm), evaporate the § acetone at room temperature, to form a dry film of the test substance on the bottom. The test compound was exposed to 10 cat fleas, Cteiwcephalides W adults (non-blood-sucking adults within 5 days after eclosion) per glass tube (1 concentration, 3 glass tubes, total 30). The test was performed three times for each concentration.

It determines life or death of fleas 24 hours and 48 hours after exposure, and calculates the median lethal concentration (LC _5.) From the concentration and mortality by probit method. The results are shown in Table 2.

Test Example 2: Drug efficacy test against Haemaphysalis longicornis

Lml (concentration: lg / niL 10g / ml) of an acetone solution of the test compound was dropped on the inner surface of a 9cm-dia petri dish with a micropipette. After the inner surface of the petri dish was dried, 60 to 180 larvae of mites were placed, covered with a polyethylene sheet and sealed with a rubber band. After that, the petri dish was left standing at a constant temperature of 25 ° C, a relative humidity of 100% and a constant darkness except for observation. Observations were made at regular intervals after the larvae were placed in petri dishes (gZml concentration: 5, 20, 30, 60 minutes, 2 hours, 4 hours, 24 hours, and 32 hours; concentration of 10 M gZml: 10 After 5 minutes from 30 minutes to 30 minutes, 45 minutes, 60 minutes, 2 hours, 4 hours, and 24 hours later), the number of overturning (knockdown) mites after drug contact was recorded. As a control, juvenile mites were put into a petri dish to which 1 ml of acetone was added dropwise and observed in the same manner. Do the above 2 Repeated times.

The survival rate was determined from the number of rollover mites at each observation, and the corrected mortality was calculated by the following Apot correction formula. Next, a probit-time line was drawn to determine the half-lethal time (KT5 _fl value), and the results are shown in Table 3.

Corrected mortality rate) = [(survival rate of control plot-survival rate of treated plot) Z viability of control plot] X 100 Test compound concentration (^ g / ml) τ ₅₀ ί (min)

1st time 2nd time

Compound No. 2 1 0 7 0 7 0

1 3 5 0 4 0 0

Compound No. 3 1 0 3 5 3 5

1 7 0 0 3 5 0

Compound No. 5 1 0 3 0 3 0

1 5 0 4 0

No. 10 1 0 6 0 3 5

1 7 0 0 6 0 0

No. I I 1 0 2 b 2 5

1 1 5 0 Upper 8 0

Fake shelf 0. [Δ 丄 (J U Z o

1 4 0 3 5

Compound No. 31 1 0 3 5 3 0

1 6 0 0 7 0 0

Compound No. 33 1 0 4 5 6 0

1

Compound No. 42 1 0 5 8 5 8

1 5 0 5 0

Compound No. 59 1 0 4 5 4 5

1 5 0 Test example 3: Drug efficacy test using dogs against ticks

50 young mites of phlebotophores ticks were released on the pinna of a dog (beagle, 8 months old) and artificially infested. After counting the number of mites colonized 2 days after the infestation, compound No. 3 formulated on the back of the neck was spot-on administered at a dose of 10 mg / kg. Observations were made up to 5 days after drug administration, and as a result of observing the number of parasites, the number of drops, and the life and death of the ticks, 100% of the ticks fell or died. The dogs were housed individually in cages, had free access to tap water, and were fed a predetermined amount of dog feed once a day. Similar results were obtained when Compound No. 3 was replaced with Compound No. 11.

Test Example 4: Drug efficacy test using dogs for fleas

The cat flea non-blood-sucking adults within 3 days after emergence were released on the back coat of dogs (beagle, 8 months old) and artificially parasitized, and compound No. 3 formulated on the back of the neck at 10 mg / kg The dose was administered spot-on. Three days after drug administration, fleas were collected using a flea comb and the number of fleas colonized was examined. As a result, the flea settlement inhibition rate was 100%. The dogs were individually bred in cages, fed tap water freely, and given a predetermined amount of dog feed once a day. Similar results were obtained when Compound No. 3 was replaced with Compound No. 11.

Test Example 5: Organophosphorus and Dicofol resistant insecticide tests

The formulation of Compound No. 31 was dispersed in water and adjusted to 80 ppm. The leaves of only the primary leaves of kidney beans were transplanted into cups (diameter: 7 cni, height: 4 cm), which were inoculated with an organophosphorus agent and about 30 adults of dicophor-resistant Namihadani. This was immersed for about 10 seconds in the chemical solution adjusted to the above-mentioned concentration together with kidney beans, and air-dried, and then left in a 26 ° C illuminated thermostat. On the second day after the release, survival was determined, and the mortality was calculated by the following formula. As a result, the dichophor-resistant Namihadaji showed a 100% mortality. Similar results were obtained when the preparations of Compound Nos. 59 and 60 were used instead of the preparation of Compound No. 31.

Mortality (%) = {(number of dead insects) z (number of released insects)} X 100

Test example 6: Oviposition test of two organic phosphorus agents and dichophor-resistant Nami-Nada

The formulation of Compound No. 31 was dispersed in water and adjusted to 80 ppm. Transplanted into a cup (diameter 7 cni, height 4 cm), and inoculated with an organophosphorus agent and dicofol-resistant adults, and allowed them to lay eggs for 24 hours. Was removed. This was immersed together with kidney leaves in the chemical solution adjusted to the above-mentioned concentration for about 10 seconds, air-dried, and allowed to stand in a thermostat with illumination at 26 ° C. On the 7th day of the treatment, the hatching status of the eggs was investigated, and the ovicidal rate was calculated by the following formula. As a result, dichophor-resistant Namihadaji showed an ovicidal rate of 100%. Similar results were obtained when the preparations of Compound Nos. 59 and 60 were used instead of the preparation of Compound No. 31.

Egg kill rate (%) = {(number of eggs killed) / (number of eggs laid)} X 100

Test Example 7: Insecticidal test

The preparation of compound No. 31 was dispersed in water, and rice seedlings were immersed in a chemical solution adjusted to 80 ppm for 10 seconds, air-dried, and the roots were wrapped with absorbent cotton and placed in test tubes. Then, 10 larvae of Hymetobinic force were released into this, and the mouth was covered with gauze. After 5 days, the survival of the insects was determined, and the mortality was determined in the same manner as in Test Example 3. As a result, Aedes albicans showed an insecticidal activity of 90% or more. Similar results were obtained when the preparations of Compound Nos. 59 and 60 were used instead of the preparation of Compound No. 31.

Test Example 8: Insecticidal test of Lotus cutworm

The preparation of Compound No. 31 was dispersed in water, and leaf pieces of cabbage were immersed in a chemical solution adjusted to 80 O ppm for about 10 seconds and air-dried. A wet filter paper was laid on a 9 cm diameter petri dish, and an air-dried piece was placed on it. Two or three-year-old larvae of the larvae of Spodoptera litura were released there, covered, and allowed to stand in an incubator with lighting at 26 ° C. On the 5th day after the release, survival was determined, and the mortality was determined in the same manner as in Test Example 1. As a result, the cutworm showed a mortality of 90% or more. Similar results were obtained when the preparations of Compounds N 0.59 and 60 were used instead of the preparation of Compound No. 31.

Next, formulation examples will be described.

Formulation Example 1

(1) 20 parts by weight of a compound of the formula (I) (2) N, N '—dimethylformamide

40 parts by weight

(4) Polyoxyethylene alkylphenol 8 parts by weight or more are uniformly mixed and dissolved to form an emulsion.

Formulation Example 2

(1) 5 parts by weight of a compound of the formula (I)

(2) 45 parts by weight of bentonite

(3) Kaolin 50 parts by weight or more kneaded with a small amount of water, extruded into granules, dried and granulated Formulation Example 3 '

(1) 30 parts by weight of a compound of the formula (I)

(2) 35 parts by weight of finely divided silica

(3) Fine clay 25 parts by weight

(4) Sodium formalin condensate of naphthrenesulfonic acid

(5) Dialkyl sulfosuccinate t-part

(6) Polyoxetylene alkylaryl ether sulfate 5 parts by weight or more is uniformly pulverized and mixed to obtain a wettable powder.

Formulation Example 4

(1) Compound of formula (I)

(2) Talc

The above ingredients are mixed uniformly to make a powder.

Formulation Example 5

(1) 50 parts by weight of a compound of the formula (I)

(2) 30 parts by weight of methyl sorb

(3) Polyoxetylene phenyl phenyl ether 20 parts by weight or more are uniformly mixed and dissolved to prepare a night agent.

Formulation Example 6 (1) 10 parts by weight of a compound of the formula (I)

(2) 2 parts by weight of polyvinyl alcohol

(3) 2 parts by weight of sodium alginate

(4) 86 parts by weight or more of water is uniformly stirred and mixed to form a flowable agent

Formulation Example 7

(1) 10 parts by weight of a compound of the formula (I)

(2) A mixture of 90 parts by weight or more of dimethylene glycol monoethyl ether is uniformly mixed to obtain a liquid agent.

"Industrial applicability"

According to the present invention, a composition containing a specific pyrazole compound or a salt thereof as an active ingredient, including a novel compound not described in the literature, having an excellent animal ectoparasite (mite, fleas) control effect, and A method for controlling parasites or fleas on animals using an effective amount of the compound is provided.

Claims

The scope of the claims

1. Formula (I)

[Wherein T is one CH = or a nitrogen atom, R ¹ is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, a linear alkoxy group or a tert-butoxycarponyl group, and X Is an oxygen atom, a sulfur atom, —OCH ₂ CO or an alkylene group, Y is an alkyl group optionally substituted with halogen, alkoxy, alkylthio or phenyl; an alkenyl group optionally substituted with halogen; halogen An alkynyl group optionally substituted with alkyl; a cycloalkyl group optionally substituted with alkyl, halogen or cyano; a cycloalkenyl group optionally substituted with alkyl, halogen or cyano;

{Wherein Q is an alkylene group, Cy is a 5- to 6-membered monocyclic heterocyclic group or phenyl group, and R ² is a hydrogen atom; a halogen atom; halogen, cyano, hydroxy, alkoxy or alkoxyl propyl. An alkyl group which may be substituted with halogen; an alkyl group which may be substituted with halogen; an alkylthio group which may be substituted with halogen; a cyano group; a nitro group; an alkoxyl-proponyl group; Or a cycloalkyl group optionally substituted by cyano, j is an integer of 1 to 5, and when j is 2 or more, R ² may be different from each other;

, ^ ~ ^{(R2) k}

A group (wherein R ² is as described above, and k is an integer of 1 to 5)

(Wherein R ² ′ is a hydrogen atom; a halogen atom; halogen, cyano, An alkyl group substituted with a hydroxy, alkoxy or alkoxy group; an alkoxy group optionally substituted with a halogen; an alkylthio group optionally substituted with a halogen; a cyano group; a nitro group; an alkoxycarbonyl group; A cycloalkyl group optionally substituted with alkyl, halogen or cyano; m is an integer of 1 to 4) or

(Wherein, R ² is as defined above, η is an integer of 1 to ^3, and R ³ and R ⁴ are each independently a hydrogen atom, an alkyl group or a haloalkyl group.) -A composition for controlling ticks or fleas parasitic on animals, which comprises a phenolic compound or a salt thereof as an active ingredient.

2. The composition for controlling ticks or fleas according to claim 1, wherein the animal is a companion animal, livestock or poultry.

3. A method for controlling ticks or fleas parasitic on animals, comprising using an effective amount of the compound of the formula (I) or a salt thereof according to claim 1.

4. The method according to claim 3, which controls fleas parasitic on animals.

5. The method according to claim 3, which controls ticks on animals.

6. The method according to claim 5, wherein the mite is a tick.

7. The ticks are Red ticks, Red ticks, Red ticks, Red ticks, Red ticks, Red ticks, Red ticks, Red ticks, Red ticks, Red ticks, Red ticks, Red ticks, Red ticks, Red ticks, Red ticks, Red cats 7. The method according to claim 6, wherein the method is Tiger ticks.

8. The method according to claim 7, wherein the ticks are Haemaphysalis longicornis.

9. Formula ():

[Wherein T is one CH = or a nitrogen atom, R ¹ ′ is an alkoxy group or an alkylthio group, X is an oxygen atom, a sulfur atom, 100 CH ₂ CO— or an alkylene group, and R ² ′ is a hydrogen atom; a halogen atom; an alkyl group substituted with a halogen, cyano, hydroxy, alkoxy or alkoxy group; an alkoxy group optionally substituted with a halogen; an alkylthio group optionally substituted with a halogen; A nitro group; an alkoxyl group; an alkylthiocarbonyl group or a cycloalkyl group which may be substituted with alkyl, halogen or cyano, m is an integer of 1 to 4, and R ³ and R ⁴ are each Independently a hydrogen atom, an alkyl group or a haloalkyl group], or a salt thereof.

10. T is -CH =; R ¹ 'is an alkoxy group; X is an oxygen atom; R ² ' is a halogen atom; and R ³ and R ⁴ are both alkyl groups. Or a salt thereof.

1 1. Formula (Γ '):

[Wherein T is one CH = or a nitrogen atom, and R ¹ is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, a straight-chain alkoxyl ponyl group, or a Yuichi Sharybutoxycarponyl group, X ′ is an alkylene group; R ² is a hydrogen atom; a halogen atom; an alkyl group optionally substituted with halogen, cyano, hydroxy, alkoxy or alkoxycarbonyl; an alkoxy group optionally substituted with halogen; An alkylthio group which may be substituted; a cyano group; a nitro group; an alkoxy group; an alkylthiocarbonyl group or a cycloalkyl group which may be substituted with alkyl, halogen or cyano, and k is an integer of 1 to 5; a number, R ³ and R ⁴ each independently represent a hydrogen atom, tables in an alkyl group or c port alkyl group The pyrazole - le compound or a salt thereof.

12. T is _CH =; R ¹ is a tertiary butoxycarbonyl group; 12. The pyrazole-based compound or a salt thereof according to claim 11, wherein R ³ and R ⁴ are both alkyl groups.

13. Use of a compound of formula (I) or a salt thereof according to claim 1 for the manufacture of a medicament for controlling ticks or fleas parasitic on animals.