WO2001090075A1

WO2001090075A1 - Compositions for controlling animal ectoparasites

Info

Publication number: WO2001090075A1
Application number: PCT/JP2001/004330
Authority: WO
Inventors: Sadanori Mizukoshi; Masayuki Morita
Original assignee: Ishihara Sangyo Kaisha, Ltd.
Priority date: 2000-05-25
Filing date: 2001-05-23
Publication date: 2001-11-29
Also published as: AU5882201A

Abstract

Compositions for controlling animal ectoparasites, characterized by containing as the active ingredient pyridine compounds of the general formula (I) or salts thereof in said formula (&) wherein Y is haloalkyl; m is 0 or 1; and Q is a group of the general formula (II) or an optionally substituted heterocyclic group.

Description

Specification

Animal ectoparasite control composition

Technical field

The present invention relates to a composition for controlling ectoparasites of animals, which contains a specific pyridine compound or a salt thereof as an active ingredient.

Background art

Conventionally, various pest control agents, insecticides, and the like have been used for ectoparasites of animals such as livestock and poultry animals. For example, the use of pyrethroid-based insecticides as a main component is widely used to control fleas that mainly invade the body of animals such as mammals and birds, and ingest the blood to produce nutrients. Have been. Further, the specific pyridine compound or a salt thereof which is an active ingredient of the composition for controlling ectoparasites of the present invention is described in Japanese Patent No. 2994182, JP-A-10-195072, JP-A-11-180957, Known compounds described in WO 98/57969, WO 00/35285, WO 00/35912, WO 00/35913, WO 01/9104, WO 2001/14373, and the like.

In general, flea adults are parasitized in mammals and birds, especially pets such as cats, and inhabit by sucking their blood for nutrients. When fleas infest a pet, irritation and itching can make the pet frustrated, and may cause allergic dermatitis and anemia. It can also transmit a variety of pathogens. In addition, it can also parasitize the owner, causing redness and rashes, with severe itching, and may cause allergies such as atopic dermatitis. Therefore, the present invention aims to provide a composition for controlling animal ectoparasites such as fleas.o

Disclosure of the invention

The present inventors have enthusiastically searched for compounds capable of controlling animal ectoparasites. As a result, the present inventors have specifically found that a specific pyridine-based compound which has been found to be used for agrochemicals has a particularly excellent ectoparasite control effect on animals, and completed the present invention. (I):

Wherein Y is a haloalkyl group, m is 0 or 1, and Q is

(X is an oxygen atom or a sulfur atom, and R ^{1 and} R ² are each independently a hydrogen atom

, An optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl ^{group, -! (W 1) ^} 3 group, -OR ⁴ group, - S (0) _n R ⁵ units, 1 NHR ⁶ units,

One C ⁽⁸⁾ two NO- or is R ⁹ groups or an optionally substituted Ariru group, were or R ¹ and R ² together two C (R ^10)! ^ ¹ group or, It may form a 5- or 6-membered heterocyclic group having 4 to 5 carbon atoms which may contain a nitrogen atom or an oxygen atom together with an adjacent nitrogen atom, and R ³ is an alkyl group which may be substituted, A good alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, an alkoxy group, an alkylthio group or a mono- or dialkylamino group, wherein R ⁴ is a hydrogen atom, An optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, an optionally substituted heterocyclic group Also - a C 0 R ³ group, R ⁵ is an alkyl or Jiarukirua amino group, R ⁶ is an alkyl group or Ariru group, Z is N or a C-R ⁷ radical, R ⁷ is a hydrogen atom , A halogen atom, an optionally substituted alkyl group, an alkoxy group, an alkylthio group or a nitro group, and R ⁸ and R ⁹ are each independently a hydrogen atom, an optionally substituted alkyl group, or an optionally substituted Alkenyl group, optionally substituted alkynyl group, optionally substituted aryl group or substituted R ^{1 G} and R ¹¹ are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted heterocyclic group

, -N- (R ¹² ) R ¹³ , an optionally substituted alkoxy group, and an optionally substituted alkylthio group, wherein R ¹² and R ¹³ are each independently a hydrogen atom, an optionally substituted alkyl A alkenyl group which may be substituted, an alkynyl group which may be substituted, an aryl group which may be substituted or a heterocyclic group which may be substituted;

¹ is an oxygen atom or a sulfur atom, and n is 1 or 2) or a heterocyclic group which may be substituted]] or a salt thereof as an active ingredient. The present invention relates to a composition for controlling ectoparasites in animals.

In the formula (I), the Y CF _3, CHF There _{_{CH 2 F, CF 2 C 1}} , CFC 1 2,

CC 1 _3, or a haloalkyl group such as CH _₂ CF _3, CF ₂ CF have CHB r There CH ₂ B r, are included. Among them, a haloalkyl group having 1 to 2 carbon atoms and 1 to 5 halogen atoms is desirable, and a trifluoromethyl group is more desirable.

The substituent represented by Q in the general formula (I):

RR ² , RR ⁴ , ⁷ R ⁸⁰ contained in the group (hereinafter referred to as Q ¹ group)

An optionally substituted alkyl group defined as R ⁹ , R 1, R ", R ¹² or R ¹³ ; RR ² , R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹⁰ , R", R ¹² Or an optionally substituted alkenyl group defined as R ¹³ ; an optionally substituted alkynyl group defined as RR ² , R ³ , R ⁴ , R ⁸ , R ⁹ , R ¹² or R ¹³ ; ^{As the} secondary substituent of the optionally substituted cycloalkyl group defined as ² , R ³ or R ⁴ , a halogen atom; an alkoxy group; an alkylthio group; a trialkylsilyl group; a phenyl group; A phenyl group substituted with nitro or haloalkyl; a phenyl group substituted with phenoxy which may be substituted with alkoxy or alkylthio; a phenoxy group; a phenylthio group; an amino group; Cyclic amino group C ₂ _ _6;; amino group morpholino group; a morpholino group substituted with alkyl le; 1-piperazinyl, alkyl, phenyl, 1 Piperajiniru group substituted with pyrid Le or triflate Ruo Russia methyl pyridyl; halo Gen, alkyl, alkoxy, haloalkoxy, alkylthio, phenyl (phenyl may be further substituted with halogen, alkyl, alkoxy, nitro, haloalkyl or phenoxy, phenoxy, phenylthio, cycloalkyl or cycloalkoxy A heterocyclic group which may be substituted with: a hydroxy group; a cyano group

A cycloalkyl group; an imino group; —C (W ² ) R ¹⁴ group (W ² is an oxygen atom or a sulfur atom, and R ¹⁴ is a hydrogen atom; an amino group; an amino group substituted with one or two alkyl groups; An alkyl group; an alkoxy group; an alkylthio group; or an aryl group)

An OC (W ² ) R ¹⁵ group (R ¹⁵ is an aryl group substituted with an alkyl or haloalkyl); or an alkylsulfonyl group. When the above substituent is an imino group, it may form an amidino group or an imidate group together with an amino group or an alkoxy group.

Other examples of the substituent of the optionally substituted alkyl group defined as R ¹ or R ² included in the group Q ¹ in the general formula (I) include, for example, 4-haloalkyl-1-pyridinecarboxamido. Group, N-methyl-4-haloalkyl-13-pyridine lipoxamide group, 4-haloalkyl-13-pyridinecarboxamide N-alkylenoxy group, etc. are also included. The chemical structural formulas of the general formula (I) containing these substituents are exemplified.

(Wherein, R ² is as described above, A is — (CH ₂ ), one group or one (CH ₂ ) _q -0- (CH ₂ ) _q group, and 1 is an integer of 1 to 4. And q is 1 or 2)

That is, the above compound is a dimer of the compound of the general formula (I) linked by an alkylene chain or the like. In addition, the active ingredient of the composition of the present invention includes a trimer based on such an idea.

Two of the optionally substituted aryl groups defined as R ¹ R ² , R ³ , R ⁴ , R ⁸ , R ⁹ , R ^{] 2} or R ¹³ included in the Q ¹ group in the general formula (I) As the next substituent, c Alkyl group; Haloalkyl group; Alkoxy group; Haloalkoxy group; Alkylthio group; Cycloalkyl group; Cycloalkoxy group; Alkoxycarbonyl group; Alkylcarbonyl group; Alkylcarbonyloxy group; Arylthio group; amino group; amino group substituted with one or two alkyl groups; cyano group; nitro group; and hydroxy group.

^{Two of the} optionally substituted heterocyclic groups defined as R ⁴ , R ⁸ , R ⁹ , R ¹⁰ , R ″, R ¹² or R ¹³ included in the Q ¹ group in the general formula (I) The following substituents include a halogen atom; an alkyl group; an alkoxy group; a haloalkoxy group; an alkylthio group; a phenyl group which may be substituted with halogen, alkyl, alkoxy, nitro, haloalkyl or phenoxy; a phenoxy group; Groups; cycloalkyl groups; cycloalkoxy groups and the like.

The alkyl group or alkyl moiety contained in the group Q ¹ in the general formula (I) has 1 to 6 carbon atoms, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group Those having 3 or more carbon atoms may be straight-chain or branched-chain structural isomers. The alkenyl group contained in the Q ¹ group in the general formula (I) includes those having 2 to 6 carbon atoms, such as ethenyl, propenyl, butenyl, pentenyl, and hexenyl groups. And those having 3 or more carbon atoms may be linear or branched structural isomers. Examples of the alkynyl group contained in the Q ¹ group in the general formula (I) include those having 2 to 6 carbon atoms, such as an ethynyl group, a propynyl group, a petynyl group, a pentynyl group, and a hexynyl group. Those having 4 or more carbon atoms may be straight-chain or branched-chain structural isomers. Examples of the cycloalkyl group included in the Q ¹ group in the general formula (I) include those having 3 to 8 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group.

R ¹ and R ² contained in the Q ¹ group in the general formula (I) may be joined together to contain a nitrogen atom or an oxygen atom together with an adjacent nitrogen atom. A 5- or 6-membered heterocyclic ring having 4 to 5 carbon atoms. Examples of the group include a morpholino group, a pyrrolidino group, a piperidino group, an 11-imidazolidinyl group, a 2-cyanoiminone 3-methyl-11-imidazolidinyl group, a 1-piperazinyl group, and a 4-methyl-1-piperazinyl group. Examples of the aryl group included in the Q ^] group of the formula (I) include a phenyl group, a phenyl group, a furanyl group, a pyridyl group, a naphthyl group, a benzochenyl group, a benzofuranyl group, and a quinolinyl group. The heterocyclic moiety of the optionally substituted heterocyclic group included in the Q ¹ group in the general formula (I) includes a pyridyl group, a cyenyl group, a furyl group, a pyrazinyl group, a pyrimidinyl group, a tetrahydrofuranyl group, a thiazolyl group Group containing 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur such as isooxazolyl, quinolyl, pyrazolyl, oxazolyl, oxdiazolyl, thiadiazolyl, and triazolyl And a 7-membered monocyclic group or a phenyl-fused cyclic group. The heterocyclic moiety of the optionally substituted heterocyclic group represented by Q in the general formula (I) includes 2 to 3 hetero atoms selected from a nitrogen atom, an oxygen atom and a sulfur atom. Preferred is a 7-membered monocyclic group, specifically, a bilazolyl group, an oxazolyl group

5-membered monocyclic groups such as thiazolyl, oxaziazolyl, thiadiazolyl, and triazolyl;

And a 6-membered monocyclic group.

—The secondary substituent of the optionally substituted heterocyclic group represented by Q in the general formula (I) includes a halogen atom, a nitro group, an optionally substituted alkyl group, an optionally substituted alkenyl group An optionally substituted alkynyl group, an optionally substituted aryl group, an optionally substituted heterocyclic group, an optionally substituted cycloalkyl group, a hydroxyl group, an optionally substituted alkoxy group, and an optionally substituted Alkenyloxy group, optionally substituted alkynyloxy group, optionally substituted aryloxy group, optionally substituted heterocyclic oxy group, optionally substituted cycloalkoxy group, mercapto group, optionally substituted Good alkylthio group, optionally substituted arylthio group, optionally substituted arylthio group, optionally substituted alkynylthio group, optionally substituted Riruchio group, a substituted heterocyclic ring which may Chio group, an optionally substituted Shikuroa alkylthio group, an optionally substituted carbonyl group, an alkoxy force be substituted Rubonyl group, optionally substituted arylcarbonyl group, optionally substituted carbonyloxy group, formyl group, optionally substituted ester group, optionally substituted acyl group, optionally substituted sulfonyl group, substituted Optionally substituted sulfyl group, optionally substituted sulfonyloxy group, optionally substituted alkylsulfyl group, optionally substituted sulfonylalkyl group, optionally substituted amino group, optionally substituted Examples include an isocyanato group, an optionally substituted arylalkyl group, and an optionally substituted heterocyclic alkyl group.

Of these secondary substituents, those that may be substituted include halogen atoms; cyano groups; halogen groups that may be substituted with halogen, haloalkyl, cyano, alkoxy, aryl, and alkoxy groups that may be substituted with halogen and aryl. An amino group which may be substituted with an alkylsulfonyl, an arylalkyl, a heterocyclic alkyl, an alkyl, an aryl, a 7alkylaryl, an alkylhydroxy, a cyanoalkyl, an alkynyl, an alkenyl, a cycloalkyl; an alkoxy, an alkylamino or Carbonyl group which may be substituted with alkyl; alkylthio group; aryloxy group; arylthio group; aryl group which may be substituted with halogen, haloalkoxy, alkyl or aryl; nitro group; Replace with Arylalkylcarbonyl group; cycloalkyl group; alkylsulfonyloxy group; alkylcarbonyloxy group; alkyl, haloalkyl, alkenyl, alkynyl, heterocyclic alkyl, aryloxy, aryloxyalkyl, alkoxy Alkoxycarbonylalkyl, hydroxyalkyl, cyanoalkyl, alkoxyalkyl, alkenyl, arylalkoxy, alkoxyl force isocyanato group which may be substituted by ruponylalkyl; arylalkyl, halogen, alkyl, alkoxy which may be substituted Arylalkylisocyanato group; cycloalkylcarbonyloxy group; cycloalkylisocyanato group which may be substituted with haloalkyl; alkynylalkylisocyanato group; Coxy, alkylthio, halogen, hydroxyl, haloalkoxy, nitro, or aryloxy substituted with aryloxy or arylisocyanato optionally substituted with aryloxy; heterocyclic ring optionally substituted with alkyl, alkoxy, aryl or ester Group; further substituted by a tertiary substituent such as an alkoxyisocyano group. Can be replaced by

The secondary or tertiary substituent of the optionally substituted heterocyclic group represented by Q in the general formula (I) has an alkyl group or an alkyl moiety having 1 to 6 carbon atoms, for example, Examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group and a hexyl group, and those having 3 or more carbon atoms may be those having a linear or branched structural isomer. Examples of the alkenyl group include those having 2 to 6 carbon atoms, such as ethenyl group, propyl group, butenyl group, pentenyl group, and hexenyl group, and those having 3 or more carbon atoms are straight or branched. It may have a structural isomer of the chain. Alkynyl groups include those having 2 to 6 carbon atoms, for example, ethynyl group, propynyl group, butynyl group, pentynyl group and hexynyl group, and those having 3 or more carbon atoms are linear or branched. May be structural isomers of Examples of the cycloalkyl group include those having 3 to 8 carbon atoms, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group. Examples of the aryl group include a phenyl group, a phenyl group, a furanyl group, a pyridyl group, a naphthyl group, a benzophenyl group, a benzofuranyl group, and a quinolinyl group. Examples of the heterocyclic group include 1 to 3 hetero atoms selected from nitrogen, oxygen and sulfur such as pyridyl, phenyl, phenyl, virazinyl, thiazolyl, isoxazolyl, and quinolyl. And a 5- or 6-membered monocyclic group or a phenyl-fused cyclic group. The compound of the general formula (I) may form a salt with an acidic substance or a basic substance, and the salt with the acidic substance may be a salt such as hydrochloride, hydrobromide, phosphate, sulfate, or nitrate. The salt with a basic substance may be an inorganic or organic base salt such as a sodium salt, a potassium salt, a calcium salt, an ammonium salt or a dimethylamine salt.

The compound of the general formula (I) or a salt thereof is described in Japanese Patent No. 2994182, JP-A-10-195072, JP-A-11-180957, W098 / 57969, W00 / 35285, W00 / 35912, W00 It can be manufactured according to the method described in / 35 913, W01 / 9104, TO01 / 14373 and the like.

The composition of the present invention includes: fleas; mites; lice such as lice, lice, lice, and lice; lice such as lice and lice; and lice such as lice. Although it is effective for those living on the body surface of succulent host animals, it is particularly effective in controlling fleas and mites. It is also effective against blood-sucking dipteran pests such as flies, brassicae, buyo, and sand flies.

Host animals for which the composition of the present invention is effective include dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, egrets, ferrets, and birds (e.g., pigeons, horses, myna birds, fowls, parakeets, parakeets, And pets such as black pine, canary, etc .; livestock such as porcupines, pomas, pigs and higgies; and poultry such as ducks and chickens. However, the compositions of the present invention are particularly effective on pets, especially dogs and cats. External parasites inhabit the host animal in the back, armpits, lower abdomen, inner thighs, etc.o

The above-mentioned fleas refer to ectoparasitic wingless insects belonging to the order Flea (Siphonaptera), specifically fleas belonging to the family Flea (Pulliedae), the family Flea (Ceratephyl lus) and the like. The fleas belonging to the flea family include the flea (Ctenocephal i des can is), the non-flea (Ctenocephal ides lei is), the flea (Pulex irritans), the newt flea (Echidnophaga gal l inacera), and the noptosyl noche is), Yamato flea flea (Monosyl lus anisus), 一一口ヽヽ ° flea flea (Nosopsvl lus fasciatus) and the like. The composition of the present invention is excellent in controlling fleas belonging to the family Flea among fleas, and particularly excellent in controlling fleas mainly parasitic on dogs and cats such as fleas and cats. The composition of the present invention includes, among the above-mentioned mites, Haemaphvsal is longicornis, Haemaphvsal is longicornis, Haemaphysa l is i apon i ca), Dermacentor ret iculatus, Dermacentor taiwanesi tick, It is especially good at controlling ticks such as Haemaphvsal is f lava), Ixodes ovatus, Ixodes persuicatus and Boophi lus micro lus.

The compound of the general formula (I) may be used as it is, but it can be used in the form of powders, granules, tablets, powders, capsules, premixes, liquids, emulsions, etc. together with a suitable carrier. . Suitable carriers include those normally used in feed drugs, such as lactose, sucrose, glucose, starch, wheat flour, corn flour, Examples include soybean meal, defatted rice bran, calcium carbonate, and other commercially available feed ingredients. In addition, the compound of the general formula (I) may be used together with a carrier together with various vitamins and minerals.

It can also be used in combination with amino acids, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, fragrances, preservatives and the like. Further, the compound of the general formula (I) can be mixed with or used in combination with other animal drugs such as antibacterial agents, nutritional agents, anthelmintic agents, fungicides, anticoccidial agents, etc., if necessary. In some cases, it has excellent effects. The following are preferred as other animal drugs that can be used in combination or in combination.

(A) phosphoric acid or phosphate ester

(A-1) Diethyl 0- (8-quinolyl) phenyl monothiophosphate

[Generic name: Quinchophos]

(A-2) 0, 0—Jetyl 0— (3-Clo-4-1-Methyl-1-7-coumaryl) Thiophosphate [Generic name: Coumaphos]

(A-3) 0, 0 _ getyl 0 _ phenylglyoxylonitrile oxime chohophosphate [generic name: phoxime]

(A-4) 0, 0—Jetil 0—Cyanocrotonic Benzaldoxime Thiophosphate [Generic Name: Chloroxime]

(A-5) 0, 0—Jetyl 0— (4-Bromo-1,5-dichlorophenyl) phosphorothioate [Generic name: bromophosphoethyl]

(A-6) 0, 0, 0,, 0, 1-tetraethyl-S, S, 1-methylene di (phosphorodithioate) [generic name: ethione]

(A-7) 2- (2-, 4-dichlorophenyl) -vinyl getyl phosphate. [Generic name: clovin fenvinphos]

(A-8) 〇, 0-dimethyl ◦-1 (3-methyl-4-methylthiophenyl) thionophosphate [generic name: phenthion]

(B) Carbamate compound

(B-1) 2-isopropoxyphenyl methyl carbamate [generic name: propox

(B-2) 1-Naphthyl N-methylcarbamate [Generic name: Rivalvalyl] (C) Pyrethroids ■

(C-1) (<ί-Cyan-4-fluoro-3-phenoxy) monobenzyl 3- [2- (4-chlorophenyl) 1-2-chlorovinyl] 1,2,2-dimethyl-1-cyclopropanecarboxylate [Generic name: Fulmeslik]

(C-2) N-Cyano (4-fluoro-3-phenoxy) 1-benzyl-1,2,2-dimethyl-13- (2,2-dichlorovinyl) cyclopropanecarpoxylate

[Generic name: cyfluthulin] and its enantiomers and stereoisomers (C-3) «—cyano 3-phenoxybenzyl (earth) one cis, trans one 3- (2,2-dibromovinyl) one 2,2- Dimethyl-cyclopropanecarboxylate

[Generic name: Deltamethrin]

(C-4) _α -cyano 3-phenoxybenzyl 2,2-dimethyl-3- (2,2-dichroic vinyl) monocyclopropanecarboxylate

[Generic name: cypermethrin]

(C-5) 3-phenoxybenzyl 3-cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethyl-cyclopropanecarboxylate

[Generic name: Permethrin]

(C-6) 2-cyano 3-phenoxybenzyl 2- (2-chloro-1-, α-trifluoro-ρ_toluidino) 1-3-methylbutyrate

[Generic name: Furuno linate]

(D) Amidines

(D-1) 3-Methyl-2- [2,4-dimethyl-phenylimino] -thiazolidine (D-2) 2 -— (4-chloro-2-methylphenylimino) 1-3-methylthiazolidin

(D-3) 2- (4-chloro-2-methylphenylimino) 1-3- (1-isobutylenyl) monothiazolidine

(D-4) 1,5-bis- (2,4-dimethylphenyl) -1-methyl-1,3,5-triazantamine 1,4-gen [generic name: amitraz]

(Ε) Benzoylpereas

(Ε-1) Ν- (2,6-difluorobenzoyl) 1Ν, 1 [3,5-dichloro- 4- (3-chloro-5-trifluoromethyl_2-pyridyloxy) phenyl] ゥ rea [generic name: clomouth fluazuron]

(E-2) 1— (4-phenyl phenyl) 1-3— (2,6-dibenzo benzoyl) urea [generic name: difluvenzuron]

(E-3) 1- [2,5-dichloro-4-1 (1,1,2,3,3,3-hexafluoropropoxy) phenyl] -1-3- (2,6-difluorobenzoyl) [Generic name: Rufanuron]

(E-4) 1- (2-chlorobenzoyl) 1-3- (4-trifluoromethylphenyl) ゥ rare [generic name: triflumuron]

(E-5) 1 [«— (4-chloro-<< — cyclopropylbenzylideneaminooxy) _p-tolyl] — 3— (2,6-difluorobenzoyl) ゥ rea

[Generic name: Flucycloxuron]

(E-6) 1- [1- (2-chloro-4-1-trifluoromethylphenoxy) -1-2-fluorophenyl] —3 -— (2,6-difluorobenzoyl)

[Generic name: Flufenoxuron]

(E-7) 1- [3,5-dichloro-1-4- (1,1,2,2-tetrafluoroethoxy) phenyl] -1_ (2,6-difluorobenzoyl)

[Generic name: Hexaflumuron]

(E-8) 1— (3,5-dichloro-2,4-difluorophenyl) 1 3— (2, 6-difluorobenzoyl) perea

[Generic name: Tefulvenzuron]

(F) Neonicotinoids '' (F-1) 1-(6-chloro-3-pyridylmethyl) 1 N-2 troimitazolidinyl 2- 2-iridenamine [generic name: imidacloprid]

(F-2) Nitenvilam

(F-3) Acetamiprid

(F-4) Thiome Toxam

(G) arylpyrazoles

(G-1) fipronil (G-2) arylpyrazole

(G-3) acetopyrrole

(G-4) ethipyrrole

(H) Other

(H-1) Ethyl (2 E, 4 E) — 3,7,1 1-Trimethyl-24-decadienoate [Generic name: hydroprene]

(H-2) Isopropyl (2E, 4E) — 11—Methoxy 3,7 1 1-Trimethyl 2,4 decadedienoate [generic name: mesoprene]

(H-3) 4-Phenoxyphenyl 2- (2-pyridyloxy) propyl ether [generic name: pyriproxyphen]

(H-4) (2 RS, 4 SR) — 4- (2-ethyl-1,3-dioxolan-1-ylmethoxy) 50-80% of phenyl ether (2RS, 4 SR) — 4— (2-Ethyl-1,3-dioxolan-1-41-methoxy) A mixture of 50 to 20% of phenyl-phenyl ether [common name: diofenolan] (H-5) Ethyl = 2— (4-phenoxy) Shifenoxy) ethyl carbamate

[Generic name: Phanoxycalp]

(H-6) N-cyclopropyl-1,3,5-triazine-1,2,4,6-triamine [generic name: cyromazine]

(H-7) Avermectin

(H-8) Ivermectin

(H-9) Milbemycin

(H-10) Spinosad

(H-11) valinomycin

(H-12) Monensin-

(H-13), Salinomycin

(H-14) oxytetracycline

(H-15) Levamisole

(H-16) azadirachtin

(H-17) kinoprene (H-18) Tetrahydroazadirachtin [H-19] Tebuf enozide

Among other animal drugs that can be mixed with or used in combination with the compound of the general formula (I), it is preferable to mix and use with benzoyl ureas. This is because the composition for controlling ectoparasites in animals containing the compound of the general formula (I) and benzoyl pereas as active ingredients is a ectoparasite that can be theoretically expected when each active ingredient is mixed and used together. This is because not only does it exhibit a controlling effect (additive effect), but it also exhibits an external parasite controlling effect (synergistic effect) that cannot be predicted theoretically at a specific compounding ratio. In this case, the compounding ratio of the compound of the general formula (I) to the benzoyl pereas is generally 1:60 to 60: 1, preferably 1:20 to 20: 1, more preferably 10: 1 to 1:10, Most preferably, the ratio is 5: 1 to 1: 5, and particularly preferably, the ratio is 2: 1 to 1: 2. Further, among the benzoyl perreas which can be used in combination with or used in combination with the compound of the general formula (I), it is more preferable to use them in combination with or in combination with the benzoyl pereas listed in the above (E). Nzoyl) 1 N, 1 [3,5-dichloro 1-41 (3-chloro 1-5-trifluoromethyl-2-pyridyloxy) phenyl] ゥ Rarely mixed and used most preferably. N— (2,6-dibenzo benzoyl) 1 N, 1 [3,5-dichloro mouth 4 −1 (3—chloro mouth 5—trifluoromethyl-1 2 _pyridyloxy) phenyl] It may be mixed with or used in combination with the compound of the general formula (I). However, a formulation having improved absorption properties, for example, an amorphous benzoyl urea as described in JP-A-11-92311, It is desirable to use them together.

The dose of the compound of the general formula (I) varies depending on the administration method, administration purpose, disease symptoms, etc., but is usually from 0.01 mg to 100 g, preferably from 0. 1 mg to 1 kg body weight of the host animal. It is appropriate to administer at a rate of lmg to 10g. Administration to the host is performed orally or parenterally. Examples of the oral administration method include a method in which the compound of the general formula (I) is mixed with the host animal and administered together with the feed, or a tablet, solution, capsule containing the compound of the general formula (I) , Wafers, biscuits, minced meat and the like.

For parenteral administration, for example, a compound of the formula (I) may be formulated into an appropriate formulation, and then administered intravenously, intramuscularly, intradermally, subcutaneously, or treated with spot-on. Examples thereof include a method in which the compound is taken into the body by treatment or the like, and a method in which a resin piece containing the compound of the general formula (I) is implanted under the host animal.

Next, some preferred embodiments of the composition for controlling ectoparasites in animals according to the present invention will be exemplified below, but the present invention is not limited thereto.

(1) General formula (I)

[Wherein Y, m and Q are as defined above], a composition for controlling ectoparasites in animals, comprising a pyridine compound or a salt thereof as an active ingredient.

(2) Q is

(X is an oxygen atom or a sulfur atom, and R ¹ and R ² are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, A cycloalkyl group, -C (W R ³ groups, -S (0) _n R ⁵ groups, 1 NHR ⁶ groups,

, One C (R ⁸ ) ^ ΝΟ—R ⁹ group, or R ¹ and R ² together form = C (R ^{1 Q} ) R ¹¹ group, or a nitrogen atom or oxygen together with an adjacent nitrogen atom may form a 5-membered or 6-membered heterocyclic group may 4-5 carbon atoms include atoms, R ^3,

Wherein R ⁵ , R ⁶ , Z, R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , ¹¹ , W ¹ and n are as described above).

(3) Q is. X

II

One ^C — <2

FT

Wherein X is an oxygen atom or a sulfur atom, and R ¹ and R ² are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group, -C (W Li R ³ groups, - S (0) force \ or R ¹ and R ² is a _n R ⁵ group or a NHR ⁶ group is Te summer together = C (R ^1G) R ⁿ based on, or may form a 5-membered or 6-membered heterocyclic group of the adjacent nitrogen atom a nitrogen atom or carbon atoms include an acid atom 4 with 5, R ^3, R ⁵ , R ⁶ , W ¹ and n are as described above, and R ^1Q and R ¹¹ are each independently an alkoxy group or an alkylthio group.) The ectoparasite control composition according to (1) above.

(4) Q is ヽ OR ⁴

(In the formula, X is an oxygen atom or a sulfur atom, and R ¹ is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, or an optionally substituted A cycloalkyl group, an aryl group which may be substituted, or -C (wherein R ³ is a R ³ group, and R ³ , R ⁴ and W ¹ are as described above). Composition.

(5) The composition for controlling ectoparasites according to the above (2) or (3), wherein X is an oxygen atom.

(6) R ¹ and R ² are each independently a hydrogen atom, an optionally substituted alkyl group or a C ^(W]) or a R ³ groups, or R ¹ and R ² together such connexion = C, (R ¹ ⁰⁾ to form an R "group, is an oxygen atom or a sulfur atom, an optionally R ³ is substituted alkyl group, an optionally substituted Ariru group or an alkoxy group, R ¹⁰ and R ¹¹ (3) The composition for controlling ectoparasites according to the above (3), wherein each is independently an alkoxy group or an alkylthio group.

(7) R ¹ is a hydrogen atom, R ^{2 is a} —C (R ⁸ ) 2 NO—R ⁹ group, and R ⁸ and R ⁹ are as described above. object.

(8) R ¹ and R ² are linked to form a 2 C (R ¹⁰ ) 1 N (R ¹² ) R ¹³ group, R ^{) 0} is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted heterocyclic group, and R ¹² and R ¹³ are as defined above (2) A composition for controlling ectoparasites.

(9) R ¹ is a hydrogen atom, and

(Wherein Z and R ⁷ are as defined above). The composition for controlling ectoparasites according to the above (2), wherein

(10) X is an oxygen atom, R ¹ and R ² are each independently a hydrogen atom, alkyl group, alkoxyalkyl group, alkylaminoalkyl group, C ₂ _ ₆ cyclic Aminoa alkyl group, hydroxyalkyl group, Shianoarukiru group A thiocarbamoylalkyl group, an alkylcarbonyloxyalkyl group, an alkylcarbonyl group, an arylcarbonyl group, a trifluoromethyl-substituted arylcarbonyl group, an alkoxythiocarbonyl group or an alkoxycarbonyl group, or R ¹ And R ² together form a 2 C (R ¹ "! ^ ¹ group, and R ^1G and R ¹¹ are an alkoxy group and an alkylthio group, respectively.

(11) The compound represented by the general formula (I) is N-cyanomethyl-41-trifluoromethyl-13-pyridinecarboxamide (Compound No. 1), N-ethyl-41-trifluoromethyl-13-pyridinepyridine (Compound No. 2), 4-Trifluoromethyl-13-pyridinecarboxamide 1-oxide (Compound No.3), 4-Trifluoromethyl-3-pyridinecarboxamide (Compound No.4), N-thiocarbamoylmethyl-4 1-trifluoromethyl-3-pyridinecarboxamide, N-ethoxymethyl-4 monotrifluoromethyl-3-pyridinecarboxamide, N-isopropylaminomethyl-14-trifluoromethyl-3-pyridinepyridine N-cyanomethyl-N, N-bis (4-trifluoromethylnicotinol) amine, N-acetyl-N-cyanomethyl-41 Rifluoromethyl-3-pyridincarboxamide, N-cyanomethyl-N-methyl-4-1-trifluoromethylpyridine-13-caproloxamide, 0-methyl N- (4-trifluoromethylnicotinol) thiocarbamate, N-methyl One 4-trifluoromethylpyridine —3—Carboxamide, N— (Ν ', Ν'-dimethylaminomethyl) -1-4-trifluoromethylpyridine 1-3-Carboxamide, Ν— (1-piperidylmethyl) — 4-Trifluoromethylpyridine 1 3 _carboxamide, Ν-cyanomethyl Ν— (4-trifluoromethylnicotinoyl) aminomethylpivalate, 0, S-dimethyl Ν— (4 trifluoromethylnicotinol) iminoformate, Ν-hydroxymethyl One 4-trifluoromethyl-3-pyridinepyridine, p-acetyl-41-trifluoromethyl-3-pyridinecarboxamide and methyl- (4-trifluoromethylnicotinol) ylbamate or one of them The composition for controlling an ectoparasite according to the above (1), which is at least one selected from the group consisting of oxides.

(12) The compound represented by the general formula (I) is 、 -cyanomethyl-4-1-trifluoromethyl-13-pyridine lipoxamide, Ν-ethyl-14-trifluoromethyl-3-pyridincarboxamide, 4-trifluoro Oromethyl-1-pyridinecarboxamide

The composition for controlling ectoparasites according to the above (1), which is at least one selected from the group consisting of 1-oxide and 4-trifluoromethyl-3-pyridinepyruboxamide.

(13) The compound represented by the above general formula (I), wherein the compound of formula (I) is Ν-cyanomethyl-4-trifluoromethyl—3-pyridinepyridine and / or 4-trifluoromethyl-13-pyridinepyridinecarboxamide. 1) A composition for controlling ectoparasites.

(1) The composition for controlling ectoparasites according to the above (1), wherein the compound of the general formula (I) is Ν-cyanomethyl-14-trifluoromethyl-3-pyridinepyridine.

(15) The composition for controlling ectoparasites according to the above (1), wherein the compound of the general formula (I) is 4-trifluoromethyl-3-pyridinecarboxamide.

(16) The composition for controlling ectoparasites according to the above (1), wherein Q is a heterocyclic group which may be substituted.

(17) The ectoparasite control of (16), wherein the heterocyclic group is a 5- to 7-membered monocyclic group containing 2 to 3 hetero atoms selected from a nitrogen atom, an oxygen atom and a sulfur atom. Exclusion composition.

(18) The heterocyclic group moiety is selected from a nitrogen atom, an oxygen atom, and a sulfur atom. The composition for controlling ectoparasites according to the above (16), which is a 5-membered monocyclic group containing three hetero atoms.

(19) The composition for controlling ectoparasites according to (18), wherein the 5-membered monocyclic group is a pyrazolyl group, an oxazolyl group, a thiazolyl group, an oxdiazolyl group, a thiaziazolyl group, or a triazolyl group.

(20) The heterocyclic group moiety is selected from a nitrogen atom, an oxygen atom and a sulfur atom.

The composition for controlling ectoparasites according to the above (16), which is a 6-membered monocyclic group containing three hetero atoms.

(21) a 6-membered monocyclic group,

O

0 NR ¹⁶

(In the formula, R ¹⁶ is an alkyl group.) The composition for controlling ectoparasites according to the above (20), wherein

(22) The composition for controlling ectoparasites according to (21), wherein R ¹⁶ is a methyl group or an isopropyl group.

(23) —A composition for controlling ectoparasites in animals, comprising a compound of the formula (I) and another animal drug as active ingredients.

(24) Other animal drugs include (A) phosphate or phosphate ester, (B) carbamate compounds, (C) pyrethroids, (D) amidines, (E) benzoylureas, (F) Neonicotinoids (G) The composition for controlling ectoparasites of animals according to (23), which is at least one animal drug selected from the group consisting of arylpyrazoles.

(25) The composition for controlling ectoparasites of an animal according to (23), wherein the other animal drug is a benzoylperrea.

(26) Benzoylpereas are N- (2,6-difluorobenzoyl) -1-N, 1- [3,5-dichloro-14- (3_chloro-5-trifluoromethyl-2-pyridyloxy) phenyl ] ゥ Rare, 1- (4-chlorophenyl) -3- (2,6-difluorobenzoyl) urea, 1- [2,5-dichloro-1- 4- (1,1,2,3) , 3,3-hexafluoropropoxy) phenyl] —3— (2,6-difluorobenzoyl) ゥ rea, 1 _ (2-chlorobenzoyl) 1-3— (4-trifluoromethoxyphenyl)ゥ rea, 1 [α- (4-chloro-1-cyclopropylbenzylideneaminooxy) 1 ρ-tolyl] 1 3- (2,6-difluorobenzoyl) ゥ rea, 1-[4-( 2-Chloro-4-trifluoromethylphenoxy) 1 2-fluorophenyl] _ 3— (2,6-difluorobenzoyl) perea, 1 [3,5-dichloro mouth 1 4 1 (1 , 1,2,2-tetrafluoroethoxy) phenyl] 1-3- (2,6-difluorobenzoyl) 1- (3,5-dichloro-2,4-difluorophenyl) 1-3 — (2,6-difluo benzoyl) 前記 at least one member selected from the group consisting of rare (25) The composition for controlling ectoparasites in animals.

(27) Benzoylpereas are Ν— (2,6-difluorobenzoyl) — Ν, 1- [3,5-dichloro-4 _ (3 chloro-5-trifluoromethyl-2-pyridyloxy) phenyl] (4) The composition for controlling ectoparasites of an animal according to the above (25), which is rare.

(28) A method for controlling ectoparasites, wherein the composition according to (1) or (23) acts on ectoparasites of animals.

(29) The method according to the above (28), wherein the ectoparasite is a flea.

(30) The method according to the above (29), wherein the flea is a flea belonging to the family Flealaceae or the Family Fragidae.

(31) The method according to the above (29), wherein the fleas are fleas belonging to the family Flea family.

(32) ′ The method according to the above (31), wherein the fleas belonging to the family Flea are flea, cat flea, human flea, nit lift flea, capto flea, flea flea, or European flea.

(33) The method according to the above (31), wherein the fleas belonging to the family Flea are fleas or cat fleas.

(34) The method according to (28), wherein the ectoparasite is a mite.

(35) The method according to (28), wherein the ectoparasite is a tick.

(3 6) The ticks are the ticks of the tick, the tick, the tick, The method according to the above (35), which is Ivan ticks, Tick ticks, Ixodid ticks, Schulce ticks, or Tick ticks.

(37) The method according to (28), wherein the animal is a domestic animal or a cat.

(38) The method according to (28), wherein the animal is a cut.

(39) Pets are dogs, cats, mice, rats, hamsters, guinea pigs, squirrels

(38) The method according to the above (38), which is a heron, a heron, a ferret, a note, a worm, a mysterious bird, a sparrow, a parakeet, a pine tree, or a canary.

(40) The method according to (38), wherein the pet is a dog or cat.

(41) The orally administered composition of (1) or (23) to an animal to control ectoparasites that infest the animal's back, armpits, lower abdomen, inner thighs, etc.

8) Method. Example '

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

Test example 1

Within 100 days after emergence, 100 cat flea unblooded adults were released on the back coat of a dog (beagle male, 8 months old, weighing 9.0 kg) and parasitized. Four days after the first artificial flea parasitism, the fleas were collected using a flea picking comb and the number of fleas colonized was examined. Flea infestation was performed twice at weekly intervals.

At the same time as the start of the second artificial infestation of fleas, the test conjugate (Compound No. 1 or Compound No. 4) 1 OragZkg was filled into a gelatin capsule and administered once by oral gavage with about 10 ml of water. The dose was calculated from the body weight immediately before administration. The dogs were bred in cages, fed tap water freely, and fed a predetermined amount of dog feed (DEQ, Oriental Yeast Co., Ltd.) once a day.

Four days after the second artificial flea parasitism, fleas were collected using a flea comb and the number of settled fleas was examined. I asked. As a result, the rate of inhibition of flea fixation of Compound No. 1 and Compound No. 4 was 98.2% and 87.2%, respectively. Test example 2

The cat flea non-blood-sucking adults within 3 days after emergence are released on the back coat of dogs (beagle male, 8 months old, weighing 9.0 kg) and parasitized. Four days after the first parasitism of the first fleas, collect the fleas using a flea comb and check the number of fleas colonized. Flea infestation is performed twice at weekly intervals.

The test compound (compound No. 1 or compound No. 4) and N— (2,6-difluorobenzoyl) -N,-[3, 5] at the start of the second artificial flea parasitism —Diclo 一 1-41 (3-—1-5-5-trifluoromethyl-2-pyridyloxy) phenyl] ゥ Areas prepared in amorphous form are each filled into gelatin capsules by 15 mgZkg, and about 10 ml of water With a single oral gavage. The dose can be calculated from the body weight immediately before administration. Dogs are kept in cages, fed with tap water freely, and given a predetermined amount of dog feed (DEQU, Oriental Yeast Co., Ltd.) once a day. Four days after the second artificial flea parasitism, fleas were collected using a flea comb, and the number of fleas settled was checked. Is obtained.

In addition, 14 or 21 days after drug administration, flea adults are released to dogs and parasitized. After releasing the eggs born 4 days after release, transfer them to a petri dish. After collection, the hatchability of the eggs is examined and found to have excellent residual efficacy.

Test example 3

Release adult, young or juvenile mites of Dermatophagoides farinae to the egret and establish it. The test compound (compound Νο · 1 or compound No. 4) 3 O mg / kg is orally administered to investigate the status of mite colonization and blood sucking. After that, the condition of molting, spawning and hatching will be investigated. It can be seen that each of the survey items has an excellent acaricidal effect as compared to the non-administered group.

Test example

Release adult, young or young mites of the ticks, Haemaphysalis longicornis, to the egret. Test compound (Compound No. 1 or Compound No. 4) and N— (2,6-difluorobenzoyl) -N, 1- [3,5-dichloro-4-1 (3-chloro-5-trifluoromethyl-2-) Pyridyloxy) phenyl] urea was formulated as amorphous Each of them is orally administered at a dose of 3 O mg / kg, and the status of mite colonization and blood sucking are investigated. After that, the condition of molting, spawning and hatching will be investigated. It can be seen that each of the survey items has an excellent acaricidal effect compared to the non-medicated group. Industrial applicability

According to the present invention, a specific pyridine compound can be provided as an animal ectoparasite control agent.

Claims

The scope of the claims

-General formula (I)

Wherein Υ is a haloalkyl group, m is 0 or 1, and Q is

(X is an oxygen atom or a sulfur atom, and R ¹ and R ² are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, Good cycloalkyl group,-CiW R ³ group, -OR ⁴ group, -S (0) _n R ⁵ group, — NHR ⁶ group,

Is a C (R ⁸ ) 2 NO—R ⁹ group or an aryl group which may be substituted, or R ¹ and R ² together form = C (R ¹⁰ )! ^ ¹¹ group, Alternatively, it may form a 5- or 6-membered heterocyclic group having 4 to 5 carbon atoms which may contain a nitrogen atom or an oxygen atom together with an adjacent nitrogen atom, and R ³ is an alkyl group which may be substituted, also an alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group, an optionally substituted Ariru group, an alkoxy group, or an alkylthio radical is a mono- or dialkylamino group, R ⁴ is atom An optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, an optionally substituted heterocycle Group or C 0 is R ³ group, R ⁵ is an alkyl or Jiarukirua amino group, R ⁶ is an alkyl group or Ariru group, Zeta is Ν or a C-R ⁷ radical, R ⁷ is a hydrogen atom, R ⁸ and R ⁹ are each a halogen atom, an optionally substituted alkyl group, an alkoxy group, an alkylthio group or a nitro group. A hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group or an optionally substituted heterocyclic group, R ^{1 G} and R ¹¹ each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted heterocyclic group, one N— (R ¹² ) R ¹³ group, R ¹² and R ¹³ each independently represent a hydrogen atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, or an alkyl group which may be substituted; An optionally substituted alkynyl group, an optionally substituted aryl group or an optionally substituted heterocyclic group, W ¹ is an oxygen atom or a sulfur atom, and n is 1 or 2, or Good heterocycle The composition for controlling ectoparasites in animals, comprising, as an active ingredient, a pyridine compound represented by the formula:

2. Q

ί

I C1 ₂

(In the formula, X is an oxygen atom or a sulfur atom, and R ^] and R ² are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, a substituted or unsubstituted cycloalkyl ^{group, -! (^ W 1)} ^ 3 groups, - S (0) or is a _n R ⁵ group or a NHR ⁶ group or R ¹ and R ^2, the summer together two C a (R ^{1 G)} R group, or may form a 5-membered or 6-membered heterocyclic group adjacent nitrogen atom with or the number of carbon atoms including the nitrogen atom or oxygen radicals 4-5 Te, R ³ is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, an alkoxy group, an alkylthio group or a monoalkyl group. Or a dialkylamino group; R ⁵ is R ⁶ is an alkyl group or an aryl group; R ^{1 G} and R ^{] 1} are each independently an alkoxy group or an alkylthio group; W ¹ is an oxygen atom or sulfur 2. The composition for controlling ectoparasites in animals according to claim 1, wherein n is 1 or 2.

3. The composition for controlling ectoparasites of an animal according to claim 1, comprising a compound of the general formula (I) or a salt thereof and another animal drug as active ingredients.

4. The composition for controlling an animal parasite according to claim 3, wherein the other animal drug is a benzoylurea.

5. Benzoylpereas are N- (2,6-difluorobenzoyl) -1-N, 1- [3,5-dichloro mouth_4-1-1 (3_chloro-5-trifluoromethyl-12-pyridyloxy) phenyl] peryl 5. The composition for controlling ectoparasites in animals according to claim 4, wherein the composition is:

6. A method for controlling ectoparasites, which comprises causing the composition according to claim 1 or 3 to act on ectoparasites of animals.

7. The method according to claim 6, wherein the ectoparasite is a flea.

8. The method according to claim 6, wherein the ectoparasite is a mite.