WO2001014340A1

WO2001014340A1 - Agents for controlling animal diseases caused by endoparasites

Info

Publication number: WO2001014340A1
Application number: PCT/JP2000/005567
Authority: WO
Inventors: Kyuya Morino; Shuichi Yotsuya; Masayuki Morita
Original assignee: Ishihara Sangyo Kaisha, Ltd.
Priority date: 1999-08-19
Filing date: 2000-08-18
Publication date: 2001-03-01
Also published as: AU6597300A

Abstract

Agents for controlling diseases caused by endoparasites which contain as the active ingredient compounds represented by general formula (I) wherein Y represents haloalkyl; m is 0 or 1; and Q represents formula (II) wherein X is O or S; R1 and R2 represent each H, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, -C(W1)R3, -S(O), R4, -NHR5, formula (III), -C(R7) or =NO-R8, or R1 and R2 may together form =C(R9)R10 or, together with the nitrogen atom adjacent thereto, a 5- or 6-membered heterocycle (wherein R3 represents optionally substituted alkyl, etc.; R4 represents alkyl, etc.; R5 represents alkyl, etc.; Z is N or -C-R6 (wherein R6 represents H, halogeno, optionally substituted alkyl, etc.); R7 and R8 independently represent each H, optionally substituted alkyl, etc.; R9 and R10 independently represent each H, optionally substituted alkyl, etc.; W1 represents O or S; and n is 1 or 2) or an optionally substituted heterocycle.

Description

Specification

Control agent for animal diseases caused by endoparasites

"Technical field"

The present invention relates to an agent for controlling animal diseases caused by internal parasites, which contains a specific pyridine compound or a salt thereof as an active ingredient. The animal disease controlling agent is useful, for example, as an agent for controlling a parasite such as coccididium which is parasitic on the body of an animal.

"Background technology"

Conventionally, various pest control agents and insecticides have been used for endoparasites of animals such as livestock, poultry and pets. For example, it is an endoparasitic protozoan belonging to the genus Eimeria and is widely used in various livestock and poultry such as chickens for controlling coccididium. For example, a sulfa agent; a quinoline agent; an antithiamine agent; And polyether antibiotics such as salinomycin, lasalocid, etc .;

Further, specific pyridine compounds or salts thereof which are active ingredients of the animal disease controlling agent of the present invention are described in JP-A-6-321903, JP-A-10-195072, JP-A-11-180957, WO98 And known compounds described in WO 0/359 9 12, WO 00/359 21, WO 00/35991, and the like. However, it has not been known to use these compounds as animal disease controlling agents.

"Disclosure of the invention"

Generally, animal diseases caused by endoparasites are caused by parasites parasitizing the body of an animal host. Endoparasites that cause animal diseases often infest livestock, poultry, and pets in the stomach, intestinal tract, lungs, heart, liver, blood vessels, subcutaneous, and lymphoid tissues, causing serious conditions. Animal diseases caused by endoparasites cause anemia, malnutrition, weakness, weight loss, damage to the intestinal tract wall and other tissues and organs, and if left untreated, hosts infected with endoparasites will die.

In addition, coccidiosis, one of the animal diseases caused by endoparasites, causes enormous economic loss, especially in the poultry industry. In addition to chickens, it is one of the diseases that causes problems when raising cattle, sheep, rabbits, dogs and cats. Therefore, coccidiosis Control can have tremendous benefits in the poultry industry, the livestock industry, and pet care. Then, based on such a concept, the present invention provides an agent for controlling animal diseases caused by endoparasites.

The present inventors have enthusiastically searched for compounds that can control animal diseases caused by endoparasites, particularly coccidiosis. As a result, they have found that a specific pyridine compound or a salt thereof, which has been found to be used for agricultural chemicals, has an effect of controlling animal diseases caused by endoparasites, and completed the present invention.

That is, the present invention provides a compound represented by the general formula (I):

M is 0 or 1, and Q is

(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, Good cycloalkyl group,-(UW ¹ )! ^ Group, -S (O)

R ⁵ groups,

, — C (R ⁷ ) = N〇—R ⁸ group, or R ¹ and R ² together form = C (R ⁹ ) R ^{1 D} group, or a nitrogen atom with an adjacent nitrogen atom or It may form a 5- or 6-membered heterocyclic group having 4 to 5 carbon atoms which may contain an oxygen atom, and R ³ may be an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted good § Rukiniru group, an optionally substituted cycloalkyl group, an optionally substituted Ariru group, an alkoxy group, an alkylthio group or a mono- or dialkylamino group, R ⁴ is an alkyl or dialkylamino group, R ⁵ Is an alkyl group or a An aryl group, Z is N or - C-R ⁶ group, R ⁶ is a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkoxy group, an alkylthio group or a nitro group, R ⁷ and R ⁸ is each independently 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 And

R ⁹ and R ^ID are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted heterocyclic group, —N— (R ^M ) R ¹² group, R ^u and R ¹² are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkylthio group; Alkynyl group, optionally substituted aryl

— Is an oxygen atom or a sulfur atom, and n is 1 or 2) or an optionally substituted heterocyclic group. The present invention relates to an agent for controlling animal diseases caused by internal parasites, which comprises a compound or a salt thereof as an active ingredient.

In the general formula (I), Y represents CF ₃ , CHF ₂ , CH ₂ F, CF ₂ C 1, CFC 1 ₂ ,

_{_{_{CC 1 3, CH 2 CF 3}}} , CF 2 CF 3, includes a haloalkyl group such as CHB r _2, C HB r. 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 contained in the group (hereinafter referred to as Q ¹ ^{^{group), R 3, R 6 R}} 7, R 8, R 9, R, R u or alkyl group which may be substituted is defined as R ^12; R ^{^{', R 2, R 3,}} R 7, R 8, R 9, R' °, R u or defined which may be substituted an alkenyl group as ^{^{R 12; R ', R 2}} , R 3, R 7 As the secondary substituent of the optionally substituted alkynyl group defined as, R ⁸ , R ¹¹ or R ¹² and the optionally substituted cycloalkyl group defined as R ¹ , R ² or R ³ , halogen may be used. Atom; alkoxy group; alkylthio group; trialkylsilyl group; phenyl group; halogen atom, alkyl group A phenyl group substituted with an alkoxy group, a nitro group or a haloalkyl group; a phenyl group substituted with a phenoxy group which may be substituted with an alkoxy group or an alkylthio group; a phenoxy group; a phenylthio group; an amino group; amino group substituted 1 pc or 2 pcs; C ₂ - ₆ cyclic amino group; a morpholino group; alkyl groups substituted morpholino group; 1 Piperajiniru group, alkyl group, phenyl group, pyridyl group or Torifuruoro Chirupirijiru group 1-piperazinyl group substituted with: a heterocyclic group which may be substituted; hydroxy group; cyano group; cycloalkyl group; imino group; —C (W ² ) R ¹³ group (W ² is an oxygen atom or a sulfur atom in and, R ¹³ is a hydrogen atom, an amino group, an alkyl group of 1 to case or two positions substituted amino group, an alkyl group, alkoxy group, alkylthio Group or Ariru a group) or a -OC (W ²⁾ R ¹⁴ group (R ¹⁴ is Ariru group substituted with an alkyl group or a haloalkyl group) or alkyl Rusuruhoniru 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. In addition, as a substituent of an alkyl group which may be substituted and defined as R ′ or R ² contained in the group Q ¹ in the general formula (I), for example, 4-haloalkyl-3-pyridinyl lipoxamide Groups, N-methyl-4-haloalkyl-l-pyridinecarboxamide groups, 4-haloalkyl-3-pyridinecarboxamide-N-alkyleneoxy groups, and the like. The chemical structural formula of the general formula (I) containing these substituents is shown below.

(Wherein, R ² are as defined above, A is - (CH _2), - group or _{_{- (CH 2) q -0 -}} (CH 2) q - group wherein 1 is an integer from 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 animal disease controlling agent of the present invention includes a trimer based on such a concept.

Defined as ^{^{^{R 3, R 7, R 8}}} , R u or R ¹² included in the Q ¹ group in the general formula (I) Examples of the secondary substituent of the substituted aryl group include a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, a cycloalkyl group, a cycloalkoxy group, an alkoxycarbonyl group, and an alkyl group. Examples thereof include a sulfonyl group, an alkylcarbonyloxy group, an aryl group, an aryloxy group, an arylthio group, an amino group, an amino group substituted with one or two alkyl groups, a cyano group, a nitro group, and a hydroxy group.

A secondary substituent of an optionally substituted heterocyclic group defined as R ⁷ , R ⁸ , R ⁹ , R ′ ° R ¹ ′ or R ¹² included in the group Q ¹ in the general formula (I) And the tertiary substituent of the optionally substituted heterocyclic group defined as the secondary substituent in the Q ¹ group includes a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, a phenyl group. (The phenyl group may be substituted with a halogen atom, an alkyl group, an alkoxy group, a nitro group, a haloalkyl group or a phenoxy group), a phenoxy group, a phenylthio group, a cycloalkyl group, a cycloalkoxy group and the like. Can be The alkyl group or alkyl moiety contained in the Q ¹ group in the general formula (I) includes those having 1 to 6 carbon atoms, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. Those having 3 or more carbon atoms may be straight-chain or branched-chain structural isomers. The alkenyl group contained in R ¹ or R ² has 2 to 6 carbon atoms, for example, ethenyl group, propenyl group, butenyl group, pentenyl group, hexenyl group, and has 3 or more carbon atoms. May be straight-chain or branched-chain structural isomers. The alkynyl group contained in R ¹ or R ² has 2 to 6 carbon atoms, for example, ethynyl group, propynyl group, butyl group, pentynyl group, hexynyl group, and has 3 or more carbon atoms. It may be straight or branched structural isomerism. Examples of the cycloalkyl group contained in R ¹ or R ² include those having 3 to 8 carbon atoms, for example, 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 taken together and may contain a nitrogen atom or an oxygen atom together with an adjacent nitrogen atom. A 5- or 6-membered complex having 4 to 5 carbon atoms. Examples of the ring group include a morpholino group, a pyrrolidino group, a piperidino group, Examples thereof include a midazolidinyl group, 2-cyanoimino-3-methyl-1-imidazolidinyl group, 1-piperazinyl group and 4-methyl-1-piperazinyl group.

Examples of the aryl group included in the Q ¹ group in the general formula (I) 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.

The heterocyclic moiety of the optionally substituted heterocyclic group contained in the Q ¹ group in the general formula (I) includes a pyridyl group, a phenyl group, a furyl group, a virazinyl group, a thiazolyl group, an isooxazolyl group, and a quinolyl group A 5- or 6-membered monocyclic group containing 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, such as pyrazolyl, oxazolyl, oxaziazolyl, thiadiazolyl, and triazolyl, or And phenyl-fused cyclic groups.

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. A monocyclic group is preferably a membered member, and specific examples include a pyrazolyl group, an oxazolyl group, a thiazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a triazolyl 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, Alkynyl group which may be substituted, aryl group which may be substituted, heterocyclic group which may be substituted, cycloalkyl group which may be substituted, hydroxyl group, alkoxy group which may be substituted, alkenyl which may be substituted Oxy group, optionally substituted alkynyloxy group, optionally substituted aryloxy group, optionally substituted heterocyclic oxy group, optionally substituted cycloalkoxy group, mercapto group, optionally substituted Alkylthio group, optionally substituted arylthio group, optionally substituted alkoxylthio group, optionally substituted alkynylthio group, optionally substituted An optionally substituted heterocyclic thio group, an optionally substituted cycloalkylthio group, an optionally substituted carbonyl group, an optionally substituted alkoxy group, a carbonyl group, an optionally substituted arylcarbonyl group, Carbo that may be substituted Niloxy group, formyl group, ester group which may be substituted, acyl group which may be substituted, sulfonyl group which may be substituted, sulfyl group which may be substituted, sulfonyloxy group which may be substituted, substitution Alkylsulfyl group which may be substituted, sulfonylalkyl group which may be substituted, amino group which may be substituted, isocyanato group which may be substituted, arylalkyl group which may be substituted, complex which may be substituted And a ring alkyl group.

Of these secondary substituents, those which may be substituted are halogen atoms; cyano groups; alkyl groups which may be substituted with halogen atoms, haloalkyl groups, cyano groups, alkoxy groups, aryl groups; halogen atoms, aryl groups. An alkoxy group optionally substituted with: a hydroxyl group; an alkylsulfonyl group, an arylalkyl group, a heterocyclic alkyl group, an alkyl group, an aryl group, an alkylaryl group, an alkylhydroxy group, a cyanoalkyl group, an alkynyl group, and an alkenyl group An amino group optionally substituted with a cycloalkyl group; an alkoxy group, an alkylamino group, a carbonyl group optionally substituted with an alkyl group; an alkylthio group; an aryloxy group; an arylthio group; a halogen atom, a haloalkoxy group, or an alkyl Or aryl which may be substituted with aryl group A nitro group; an arylcarboxy group optionally substituted by a halogen atom or a nitro group; a cycloalkyl group; an alkylsulfonyloxy group; an alkylcarbonyloxy group; an alkyl group, a haloalkyl group, an alkenyl group, an alkynyl group , A heterocyclic alkyl group, an aryloxy group, an aryloxyalkyl group, an alkoxy group, an alkoxycarbonylalkyl group, a hydroxyalkyl group, a cyanoalkyl group, an alkoxyalkyl group, an alkenyl group, an arylalkoxy group, and an alkoxyl group. An arylalkyl group, a halogen atom, an alkyl group, or an aryl group which may be substituted with an alkoxy group; a cycloalkylcarbonyloxy group; a haloalkyl group. A cycloalkyl isocyanato group; an alkynylalkyl isocyanate group; an alkyl group, an alkoxy group, an alkylthio group, a halogen atom, a hydroxyl group, a haloalkoxy group, a nitro group, a halogen-substituted aryloxy group, or an aryloxy group. An aryl isocyanato group which may be substituted; an alkyl group, an alkoxy group, A heterocyclic group which may be substituted by an aryl group or an ester group; which may be substituted by a tertiary substituent such as an alkoxyisocyano group.

The secondary substituent of the optionally substituted heterocyclic group represented by Q in the general formula (I), the alkyl group or the alkyl moiety in the tertiary substituent are those 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 straight-chain or branched-chain structural isomers. 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 heteroatoms 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.

"Best mode for carrying out the invention"

Some pyridine compounds or salts thereof which are desirable as the active ingredient of the agent for controlling endoparasite-induced animal diseases of the present invention are illustrated below, but the present invention is not limited thereto. (1) Q is

X

II

One c-

(X is an oxygen atom or a sulfur atom, and R ¹ and R ^z are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, Cycloalkyl group, -C (W ³ R group, -S (〇) group,

, — C (R ⁷ ) = NO—R ⁸ groups, or R ¹ and R ² together form a C (R ⁹ ) R ^ie group, or a nitrogen or oxygen atom with an adjacent nitrogen atom May form a 5- or 6-membered heterocyclic group having 4 to 5 carbon atoms, wherein R ³ is an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted A alkynyl group, a cycloalkyl group which may be substituted, an aryl group which may be substituted, an alkoxy group, an alkylthio group or a mono- or dialkylamino group, R ⁴ is an alkyl group or a dialkylamino group, and R ⁵ is an alkyl group Z is an N or —C—R ⁶ group, R ⁶ is a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkoxy group, an alkylthio group or a nitro group, R ⁷ and R ⁸ is each independently 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. Yes,

R ⁹ and R ^{1 Q} each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted heterocyclic group, — N _ (R ^M ) R ¹² group R ¹¹ and R ¹² are each independently 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. A compound of the above general formula (I) or a salt thereof. (2) In the compound of the general formula (I), Q is

X

II

— ^C- one

(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, cycloalkyl group which may be substituted,-(UW ¹ )! ^ Group, -S (0) _n R ⁴ group or —NHR ⁵ group, or R ¹ and R ² are taken together as = C (R ⁹⁾ R ^ie based on, or may form a 5-membered or 6-membered heterocyclic group together with the adjacent nitrogen atom a nitrogen atom or oxygen atom which may contain carbon atoms. 4 to 5, R ³ is location Alkyl group which may be substituted, alkenyl group which may be substituted, alkynyl group which may be substituted, cycloalkyl group which may be substituted, aryl group which may be substituted, alkoxy group, alkylthio group or mono- or dialkyl amino groups der Ri, R ⁴ is an alkyl group Other is a dialkylamino group, R ⁵ is an alkyl or Ariru group, R ⁹ and R ^{1 fl} are each independently an alkoxy group or an alkyl Chio group, W ¹ is an oxygen atom or a sulfur atom, n Is 1 or 2.) or a salt thereof according to the above (1).

(3) The compound of the above-mentioned (1), wherein X is an oxygen atom, or a salt thereof.

(4) R ¹ and R ² are each independently a hydrogen atom, an alkyl group which may be substituted, or —C (W is a R ³ group, or R ¹ and R ² are-緖(R ⁶ ) forms a R ⁷ group, W ¹ is an oxygen atom or a sulfur atom, R ³ is an optionally substituted alkyl group, an optionally substituted aryl group or an alkoxy group, R ⁶ and The compound of the above (1), (2) or (3), wherein R ⁷ is independently an alkoxy group or an alkylthio group, or a salt thereof.

(5) The above-mentioned (1) or wherein R ¹ is a hydrogen atom and R ^{2 is a} —C (R ⁷ ) NO—R ⁸ group.

The compound of (3) or a salt thereof.

(6) R ¹ and R ² together form a = C (R ⁹ ) N (R ") R ¹² group, wherein R ⁹ , R ¹¹ and R ' ² are the same or different, a hydrogen atom, An optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, The compound of the above-mentioned (1) or (3), which is an aryl group or an optionally substituted heterocyclic group, or a salt thereof.

(7) R ¹ is a hydrogen atom, and R ² is

Wherein Z is an N or —C—R ⁶ group, and R ⁶ is a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkoxy group, an alkylthio group or a nitro group. Or the compound of (3) or a salt thereof.

(8) X is an oxygen atom, and R ¹ and R ² are each independently a hydrogen atom, an alkyl group, an alkoxyalkyl group, an alkylaminoalkyl group, a C ₂ _ ₆ cyclic aminoalkyl group, a hydroxyalkyl group, a cyanoalkyl 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 The compound of the above-mentioned (1), wherein R ⁹ and R ″ are an alkoxy group and an alkylthio group, respectively, or a salt thereof, wherein the compound forms a == C (R ⁹ ) R ^lfl group.

(9) a 5-membered monocyclic ring in which the heterocyclic group portion of the optionally substituted heterocyclic group represented by Q contains 2 to 3 hetero atoms selected from a nitrogen atom, an oxygen atom and a sulfur atom A compound of the above general formula (I) or a salt thereof, which is a group represented by the formula:

(10) a 5-membered monocyclic group containing 2 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom is a pyrazolyl group, an oxazolyl group, a thiazolyl group, an oxazidiazolyl group, a thiadiazolyl group or The compound of (9), which is a triazolyl group, or a salt thereof.

Among the compounds of the above (8), more desirable compounds are N-cyanomethyl-14-trifluoromethyl-3-pyridinepyridine (compound No. 1), N-ethyl-4-trifluoromethyl-3 —Pyridine power Lupoxamide (Compound No.2), 4-Trifluoromethyl—3-Pyridinecarboxamide 1-oxide (Compound No.3), 4-Trifluoromethyl-13-pyridinecarboxamide, N-thiocal Bamoylmethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-ethoxymethyl-4-trifluoromethyl-3-pyridinepyridine, lipoxamide N-isopropylaminomethyl-4-trifluoromethyl-3-pyridinecarbo Oxamide, N-cyanomethyl-N, N-bis (4-trifluoromethylnicotinoyl) amine, N-acetyl-N-cyanomethyl- 4-trifluoromethyl-3-Pyridinecarboxamide, N-cyanomethyl-N- Methyl-4-trifluoromethylpyridine-3-carboxamide, O-methyl N- (4-trifluoromethylnicotinoyl) thiocarbamate, N-methyl-4-trifluoromethylpyridin-3-carboxamide, N— (Ν ', N '—Dimethylaminomethyl) —4-Trifluoromethylpyridine—3-Carpoxa De, Ν- (1 over piperidyl) -4-triflate Ruo Russia methylpyridine - 3-carboxamide, Nyu- Shianomechiru

Ν— (4-trifluoromethylnicotinol) aminomethylpivalate, 0, S-dimethyl Ν— (4-trifluoromethylnicotinol) iminoformate, Ν—hydroxymethyl—4-trifluoromethyl-3 —Pyridinecarboxamide, Ν-acetyl-4-trifluorotrifluoromethyl-3-pyridinepyridinecarboxamide or methyl Ν- (4-trifluoromethylnicotinol) Can be

WO 00/35912. WO 00/35912. WO 00/35912. WO 00/35912. WO 00/35912. WO 00/35912. WO 00/35912. WO 00/35912. WO 00/35912. It can be manufactured by the method described in, for example.

The agent for controlling an animal disease caused by an endoparasite of the present invention includes nematodes such as lungworm, benthic, nodular worm, stomach parasite, roundworm, and filamentous worm; tapeworm; fluke; It is effective against parasites in the host animal, such as protozoa such as endospores, toxoplasma, and cryptosporidium. Among these endoparasites, they are effective on protozoa, and especially effective on coccidiatum. Furthermore, it is most effective for coccidium that infests poultry (chicken, ducks, geese, turkeys, etc.). Examples of coccidium parasitizing poultry For example, Eimeria tenella, Eimer acervulina, Eimeria brunetti, Eimeria maxima, Eimeria mitis, Eimeria nevice ) And Eimeria praecox.

The compound of the general formula (I) may be used as it is, but it should be used in the form of powders, granules, tablets, powders, capsules, premixes, solutions, emulsions, etc. together with a suitable carrier. Can also. Suitable carriers are those usually used in feed drugs, such as lactose, sucrose, glucose, starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other commercially available feed ingredients And the like. The compound of the present invention may be used in combination with a carrier together with various vitamins, minerals, amino acids, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, fragrances, preservatives, and the like. You can also. The concentration of the compound of formula (I) varies depending on the method of administration, the purpose of the administration, the disease symptoms, etc., but it is usually advisable to formulate the compound in a feed so that the concentration is at least 0.1 ppm. Appropriate.

`` Example J

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

A field strain of Eimeria tenella was infected and propagated in chicken chicks to obtain fresh immature oocysts. A solution of each test substance at a predetermined concentration was sensitized to the obtained fresh immature oocysts for 10 or 30 minutes. Immature Oshisuto sensitized separated center lSOOmin- ¹ 5 min Centrifuge, the supernatant removed ^ and heavy with chromic acid potassium solution was added 25 4 days Suporu Reshiyon, mature for observation Oshisuto number Oshisuto (sporulation O one cyst) Was calculated. The mortality rate was calculated using the following formula, and the results are shown in Table 1. Oocyst rate = {1-(sporulation rate of test substance sensitized) / (sporulation rate of test substance unsensitized)} X 100

Note) * indicates that only the solvent ο dimethyl sulfoxide) is used.

"Possibility of industrial use"

According to the present invention, a specific pyridine compound can be provided as an agent for controlling animal diseases caused by endoparasites.

Claims

The scope of the claims

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, Good cycloalkyl group, -C (W R ³ groups, -S (O) _nR ⁴ groups, — NH R ⁵ groups,

A C (R ⁷ ) = NO—R ⁸ group, or R ′ and R ² together form a C (R ⁹ ) R ^IQ group, or a nitrogen or oxygen atom with an adjacent nitrogen atom May form a 5- or 6-membered heterocyclic group having 4 to 5 carbon atoms, wherein R ³ is an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted A alkynyl group, a cycloalkyl group which may be substituted, an aryl group which may be substituted, an alkoxy group, an alkylthio group or a mono- or dialkylamino group, R ⁴ is an alkyl group or a dialkylamino group, and R ⁵ is an alkyl group Z is an N or —C—R ⁶ group, R ⁶ is a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkoxy group, an alkylthio group or a nitro group, R ⁷ and R ⁸ is each independently 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 And R ⁹ and R ^{1 (1} each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted heterocyclic group, — N— (R ¹¹ ) R ^{1 2} groups, an optionally substituted alkoxy group, and an optionally substituted alkylthio group, wherein R ¹¹ and R ¹² are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group Or an optionally substituted alkynyl group, an optionally substituted aryl group or an optionally substituted heterocyclic group, W is an oxygen atom or a sulfur atom, and n is 1 or 2) or Which is a heterocyclic group which may be substituted], or a salt thereof, as an active ingredient.

2. Q

(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, cycloalkyl group which may be substituted, -CW ¹ )! ^ ³ group, -S (0) „R ⁴ group or —NH R ⁵ group, or R ′ and R ² are taken together = C (R ⁹ ) R ^ie group or together with an adjacent nitrogen atom 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, and R ³ is An alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, an alkoxy group, an alkylthio group or a mono or Ri dialkylamino group der, R ⁴ is an alkyl Or a dialkylamino group, R ⁵ is an alkyl or Ariru group, R ⁹ and R ^{1 0} are each independently an alkoxy group or an alkyl Chio group, W ¹ is an oxygen atom or a sulfur atom, n represents The agent for controlling an endoparasite-induced animal disease according to claim 1, wherein the agent is 1 or 2.

3. The animal disease controlling agent according to claim 1, wherein the endoparasite is a protozoan.

4. The animal disease controlling agent according to claim 3, wherein the protozoa is coccidium.

5. The animal disease controlling agent according to claim 4, wherein the coccidium is poultry coccidia.