WO2012060317A1 - Agent de lutte contre les ectoparasites des animaux - Google Patents

Agent de lutte contre les ectoparasites des animaux Download PDF

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WO2012060317A1
WO2012060317A1 PCT/JP2011/075049 JP2011075049W WO2012060317A1 WO 2012060317 A1 WO2012060317 A1 WO 2012060317A1 JP 2011075049 W JP2011075049 W JP 2011075049W WO 2012060317 A1 WO2012060317 A1 WO 2012060317A1
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岩佐　孝男
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日本曹達株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to an animal ectoparasite control agent, a method for treating an animal suffering from an infection caused by an ectoparasite, and a method for preventing an animal from suffering from an infection caused by an ectoparasite.
  • Parasites that are parasitic on the outside of the skin and coat of animals such as livestock, poultry, and pets and that use blood and dandruff as nutrients are known.
  • Representative examples of the parasites include fleas, lice, lice, ticks, acaras, ear scabies (ear mites), scabies (hymenids), claw mites, lung mites, and acne mites (hair follicles).
  • Representative examples of the pest include diptera pests such as flies, abs and mosquitoes.
  • ectoparasites parasites and pests using nutrients such as animal blood and dandruff as described above are referred to as ectoparasites.
  • the animals When such ectoparasites infest animals, the animals may be affected by infections such as skin diseases. The infection may also infect humans.
  • ectoparasite control agents various compounds containing various compounds as active ingredients have been developed.
  • Patent Document 1, Patent Document 2, and Patent Document 7 have proposed pyrethroid compounds, pyridine compounds, arylpyrazole compounds, isoxazoline compounds, and the like as active ingredients.
  • Patent Document 3 proposes a nitrogen-containing heterocyclic compound represented by the following formula and the use of the compound as a pest control agent.
  • R 0 represents a halogen atom
  • Z represents an aryl group
  • A represents a carbon atom or a nitrogen atom
  • Y represents a nitro group
  • D1 represents a 5- to 8-membered hydrocarbon group.
  • X1 represents —NR 1 R 2 (R 1 is —C ( ⁇ W) R 130 (W represents an oxygen atom or a sulfur atom, R 130 represents an organic group, etc.), etc.
  • R 2 represents a hydrogen atom, etc.
  • n1 represents an integer of 0 to 2
  • n2 represents an integer of 0 to 3.
  • Patent Document 6 proposes a nitrogen-containing heterocyclic compound represented by the following formula and the use of the compound as a pest control agent.
  • the dotted line represents a single bond or a double bond. However, one of the two bonds indicated by the dotted line is a single bond, and the other is a double bond.
  • a 1 to A 4 represent a carbon atom or a nitrogen atom
  • Y 1 represents a halogen atom or the like
  • n 3 represents an integer of 0 to 4
  • D 2 represents a methylene group or the like
  • R 3 represents a haloalkyl group or the like
  • 1 and R 2 represent a group represented by —C ( ⁇ W) R 13 (W represents an oxygen atom, R 13 represents an alkyl group, a phenyl group, etc.), etc.
  • Z1 has a substituent.
  • An optionally substituted phenyl group or the like is shown.
  • Patent Document 4 proposes a nitrogen-containing heterocyclic compound represented by the following formula and the use of the compound as a pest control agent.
  • X2 represents a carbon atom or an oxygen atom
  • Z2 represents an unsubstituted or substituted phenyl group or heterocyclic group
  • Q represents a hydrogen atom, a halogen atom, or the like
  • q1 represents an integer of 0 to 7 S represents 0 or 1
  • a 1 to A 4 represent a carbon atom or a nitrogen atom
  • Y 2 represents a halogen atom or the like
  • n 4 represents an integer of 0 to 4
  • W represents an oxygen atom or a sulfur atom
  • R1 and R2 each independently represent a hydrogen atom or the like.
  • Patent Document 5 proposes a nitrogen-containing heterocyclic compound represented by the following formula and the use of the compound as a pest control agent.
  • D3 represents a haloalkyl group
  • Z3 represents a phenyl group which may have a substituent
  • X3 represents CH, CH 2 , NH or the like
  • Y3 represents a methyl group or the like
  • n5 represents an integer of 0 to 4
  • a 1 to A 4 each independently represents a carbon atom or a nitrogen atom
  • W represents an oxygen atom or a sulfur atom
  • R 5 and R 6 each independently represents a hydrogen atom, pyridylmethyl Indicates a group or the like.
  • JP 2002-201133 A JP 2007-529497 A WO2009 / 022746 Pamphlet JP 2008-110971 A JP 2008-133273 A JP 2009-062354 A JP 2010-536733 A
  • the present invention includes the following.
  • An ectoparasite control agent for animals comprising as an active ingredient at least one compound selected from the heterocyclic compounds represented by formula (I) and salts thereof.
  • X is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2 Represents a -6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
  • n represents the number of substitutions of X and is an integer of 0 to 5. When n is 2 or more, Xs may be the same as or different from each other.
  • a 1 and A 2 each independently represent a carbon atom or a nitrogen atom.
  • B 1 and B 2 each independently represent a carbon atom or a nitrogen atom.
  • B 1 is a carbon atom and B 2 is a nitrogen atom, the bond between B 1 and B 2 may be a double bond.
  • B 3 represents a carbon atom or an oxygen atom.
  • R 1 represents a hydrogen atom, a halogen atom, or an unsubstituted or substituted C1-6 alkyl group.
  • X 0 is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group Represents an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
  • m1 represents the number of substitutions of X 0 and is an integer from 0 to 3. When m1 is 2 or more, X 0 each other may be the same or different from each other.
  • R 11 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted amino group, or an unsubstituted or substituted group
  • R 12 represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C1-6 alkoxy group, or a halogen atom. Show.
  • R 11 and R 12 together with the carbon atom bonded, 5-8-membered having a hydrocarbon ring or a substituent R 20 5-8 membered ring having a substituent R 20
  • a ring heterocycle may be formed.
  • R 20 represents a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group An unsubstituted or substituted C1-6 alkoxy group, a nitro group, a cyano group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group , An amino group, or a substituent represented by —N (R 2 ) COR 3 .
  • R 2 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-7 acyl group, or an unsubstituted or substituted C1-6 alkoxycarbonyl group Indicates.
  • R 3 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C2-6 alkenyloxy group, an unsubstituted or substituted group; And a C2-6 alkynyloxy group having an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heterocyclic group.
  • E represents a carbon atom or a nitrogen atom.
  • An ectoparasite control agent for animals comprising as an active ingredient at least one compound selected from the heterocyclic compounds represented by formula (II) and salts thereof.
  • D represents a 5- to 8-membered hydrocarbon ring or a 5- to 8-membered heterocyclic ring.
  • R 21 is a substituent bonded to D and is an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group, an amino group, or —N ( R 2 ) represents a substituent represented by COR 3 .
  • X 1 is a substituent bonded to the condensed ring containing D and is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, unsubstituted Or a substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
  • m represents the number of substitutions of X 1 and is an integer from 0 to 6. When m is 2 or more, X 1 may be the same as or different from each other. X 1 may be substituted on the condensed ring containing D.
  • X, n, A 1 , A 2 , R 1 , E, R 2 and R 3 have the same meaning as in formula (I). )
  • An ectoparasite control agent for animals comprising as an active ingredient at least one compound selected from the heterocyclic compounds represented by formula (III) and salts thereof.
  • p represents the number of repeating methylene groups in parentheses and is either 1 or 2.
  • X, n, A 1 , A 2 , R 1 , X 1 , m, R 2 , R 3 and E have the same meaning as in formula (II).
  • An ectoparasite control agent for animals comprising as an active ingredient at least one compound selected from the heterocyclic compounds represented by formula (IV) and salts thereof.
  • the ectoparasite control agent for animals of the present invention can control ectoparasites such as ticks from animals with high effects, has a long duration of effect, has a wide action spectrum, and is low in toxicity. There are few restrictions on mixed use.
  • By administering the animal ectoparasite control agent of the present invention to an animal it is possible to prevent the animal from suffering from an ectoparasite-derived infection.
  • An infectious disease can be treated by administering the animal ectoparasite control agent of the present invention to an animal suffering from an ectoparasite-derived infection.
  • the present inventor has found that a control agent containing a specific heterocyclic compound as an active ingredient has a particularly excellent ectoparasite control effect.
  • the present invention has been completed based on these findings.
  • the animal ectoparasite control agent of the present invention is at least one compound selected from heterocyclic compounds represented by the formula (I), formula (II), formula (III) or formula (IV) and salts thereof Is contained as an active ingredient.
  • X is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2 Represents a -6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
  • n represents the number of substitutions of X and is an integer of 0 to 5. When n is 2 or more, Xs may be the same as or different from each other.
  • a 1 and A 2 each independently represent a carbon atom or a nitrogen atom.
  • B 1 and B 2 each independently represent a carbon atom or a nitrogen atom.
  • B 1 is a carbon atom and B 2 is a nitrogen atom, the bond between B 1 and B 2 may be a double bond.
  • B 3 represents a carbon atom or an oxygen atom.
  • R 1 represents a hydrogen atom, a halogen atom, or an unsubstituted or substituted C1-6 alkyl group.
  • X 0 is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group Represents an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
  • m1 represents the number of substitutions of X 0 and is an integer from 0 to 3. When m1 is 2 or more, X 0 each other may be the same or different from each other.
  • R 11 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted amino group, or an unsubstituted or substituted group
  • R 12 represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C1-6 alkoxy group, or a halogen atom. Show.
  • R 11 and R 12 together with the carbon atoms to which they are attached a 5-8 membered having a hydrocarbon ring or a substituent R 20 5-8 membered having a substituent R 20
  • a heterocycle may be formed.
  • R 20 represents a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group An unsubstituted or substituted C1-6 alkoxy group, a nitro group, a cyano group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group , An amino group, or a substituent represented by —N (R 2 ) COR 3 .
  • R 2 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-7 acyl group, or an unsubstituted or substituted C1-6 alkoxycarbonyl group Indicates.
  • R 3 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C2-6 alkenyloxy group, an unsubstituted or substituted group; And a C2-6 alkynyloxy group having an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heterocyclic group.
  • E represents a carbon atom or a nitrogen atom.
  • D represents a 5- to 8-membered hydrocarbon ring or a 5- to 8-membered heterocycle.
  • R 21 is a substituent bonded to D and is an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group, an amino group, or —N ( R 2 ) represents a substituent represented by COR 3 .
  • X 1 is a substituent bonded to the condensed ring containing D and is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, unsubstituted Or a substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
  • m represents the number of substitutions of X 1 and is an integer from 0 to 6. When m is 2 or more, X 1 may be the same as or different from each other.
  • X, n, A 1 , A 2 , R 1 , E, R 2 and R 3 have the same meaning as in formula (I). )
  • p represents the number of repeating methylene groups in parentheses and is either 1 or 2.
  • X, n, A 1 , A 2 , R 1 , X 1 , m, R 2 , R 3 and E have the same meaning as in formula (II).
  • the animal ectoparasite control agent of the present invention comprises at least one compound selected from the heterocyclic compounds represented by the formula (I) or salts thereof, preferably the heterocyclic compounds represented by the formula (II) or the compounds thereof At least one compound selected from salts, more preferably a heterocyclic compound represented by formula (III) or at least one compound selected from salts thereof, more preferably a heterocyclic compound represented by formula (IV) Or at least 1 type of compound chosen from the salt is included as an active ingredient.
  • the term “unsubstituted” means only the group that is the mother nucleus. When there is no description of “having a substituent” and only the name of the group serving as a mother nucleus is used, it means “unsubstituted” unless otherwise specified.
  • the term “having a substituent” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having the same or different structure from the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus. The number of substituents may be one, or two or more.
  • C1-6 indicate that the group serving as the mother nucleus has 1 to 6 carbon atoms. This number of carbon atoms does not include the number of carbon atoms present in the substituent.
  • a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.
  • the “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
  • the group that can be a “substituent” include halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl C1-6 alkyl groups such as a group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; C3-8 such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group A cycloalkyl group; a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-
  • C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; vinyloxy group, allyloxy group, propenyl C2-6 alkenyloxy groups such as oxy and butenyloxy groups; C2-6 alkynyloxy groups such as ethynyloxy and propargyloxy groups; C6-10 aryl groups such as phenyl and naphthyl groups; phenoxy groups and 1-naphthoxy groups C7-10 aryloxy group such as benzyl group, phenethyl group, etc .; C7-11 aralkyloxy group such as benzyloxy group, phenethyloxy group; formyl group, acetyl group, propionyl group, benzoyl group, Such as cyclohexylcarbonyl group 1-7
  • C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C2-6 alkenylsulfinyl groups such as allylsulfinyl group; C2-6 alkynylsulfinyl groups such as propargylsulfinyl group; phenylsulfinyl group, etc.
  • a C6-10 arylsulfinyl group such as: thiazolylsulfinyl group, heteroarylsulfinyl group such as pyridylsulfinyl group; C7-11 aralkylsulfinyl group such as benzylsulfinyl group, phenethylsulfinyl group; methylsulfonyl group, ethylsulfonyl group, t- C1-6 alkylsulfonyl groups such as butylsulfonyl group; C2-6 alkenylsulfonyl groups such as allylsulfonyl group; propargylsulfonyl group C2-6 alkynylsulfonyl groups of C6-10 arylsulfonyl groups such as phenylsulfonyl groups; heteroarylsulfonyl groups such as thiazolylsulfonyl
  • 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; pyridyl, pyrazinyl Groups, 6-membered heteroaryl groups such as pyrimidinyl group, pyridanidyl group, triazinyl group; saturated heterocyclic groups such as aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group; trimethylsilyl group, triethyl Examples thereof include tri-C1-6 alkyl-substituted silyl groups such as silyl group and t-butyldimethylsilyl group; trip
  • substituted may be those in which any hydrogen atom in the group is further substituted with another “substituent”.
  • X is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group, An unsubstituted or substituted C1-6 alkoxy group, nitro group, or cyano group is shown.
  • n represents the number of substitutions of X and is an integer of 0 to 5. When n is 2 or more, Xs may be the same as or different from each other.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the “C1-6 alkyl group” in X may be a straight chain or a branched chain.
  • Examples of the alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group.
  • Examples of the “C1-6 alkyl group having a substituent” in X include C3-8 cyclohexane such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, 2-cyclooctylethyl group, etc.
  • Alkyl C1-6 alkyl group fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2- Trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro -1-trifluoromethylethyl group, perfluorohexyl group, perchlor Hexyl group, C1 ⁇ 6 haloalkyl group such as 2,4,6-trichloro-hexyl group;
  • Hydroxy C1-6 alkyl groups such as hydroxymethyl group, 2-hydroxyethyl group; methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, n-propoxymethyl group, i-propoxy group C1-6 alkoxy C1-6 alkyl groups such as ethyl group, s-butoxymethyl group, t-butoxyethyl group; methoxymethoxymethyl group, 1-methoxyethoxymethyl group, 2-methoxyethoxymethyl group, 2- (1- C1-6 alkoxy C1-6 alkoxy C1-6 alkyl groups such as methoxyethoxy) ethyl group, 2- (2-methoxyethoxy) ethyl group; dimethoxymethyl group, diethoxymethyl group, 2,2-dimethoxyethyl group, 1 , 2-Dimethoxyethyl group, 3,3-dimethoxyn-propyl Di-C
  • Examples of the “C2-6 alkenyl group” in X include a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2 -Methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
  • Examples of the “substituted C2-6 alkenyl group” in X include C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group;
  • the “C2-6 alkynyl group” in X is an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2 -Methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group 1,1-dimethyl-2-butynyl group and the like.
  • Examples of the “substituted C2-6 alkynyl group” in X include C2-6 halo such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group, etc. Alkynyl group; and the like.
  • Examples of the “C1-6 alkoxy group” in X include a methoxy group, an ethoxy group, an i-propoxy group, an n-butoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, an n-pentyloxy group, i -Pentyloxy group, n-hexyloxy group and the like.
  • C1-6 alkoxy group having a substituent” in X examples include a fluoromethoxy group, a chloromethoxy group, a bromomethoxy group, a difluoromethoxy group, a dichloromethoxy group, a dibromomethoxy group, a trifluoromethoxy group, a trichloromethoxy group, Bromomethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, pentafluoroethoxy group, 4-fluorobutoxy group, 3,3,3-trifluoropropoxy group, 2,2 , 2-trifluoro-1-trifluoromethylethoxy group, perfluorohexyloxy group and other C1-6 haloalkoxy groups; methoxymethoxy group, 1-methoxyethoxy group, 2-methoxyethoxy group, ethoxymethoxy group, 1- Ethoxyethoxy group, 2-ethoxyethoxy group, 1-
  • X is preferably a halogen atom or a C1-6 haloalkyl group.
  • a 1 and A 2 each independently represent a carbon atom or a nitrogen atom.
  • the aromatic ring containing this represents a benzene ring.
  • the aromatic ring containing it represents a pyrimidine ring.
  • the aromatic ring containing it represents a pyridine ring.
  • both A 1 and A 2 are preferably carbon atoms.
  • B 1 and B 2 each independently represent a carbon atom or a nitrogen atom. It is preferred that one of B 1 or B 2 is a nitrogen atom. B 3 represents a carbon atom or an oxygen atom. When B 1 is a carbon atom and B 2 is a nitrogen atom, the bond between B 1 and B 2 may be a double bond. When B 1 is a nitrogen atom and B 2 and B 3 are both carbon atoms, the heterocycle containing the same represents a pyrrolidine ring. When B 2 is a nitrogen atom and both B 1 and B 3 are carbon atoms, the heterocycle containing the same represents a pyrroline ring (also known as 3,4-dihydro-2H-pyrrole ring).
  • B 1 is a carbon atom
  • B 2 is a nitrogen atom
  • B 3 is an oxygen atom
  • the heterocycle containing this is an isoxazoline ring (also known as a 4,5-dihydroisoxazole ring).
  • R 1 represents a hydrogen atom, a halogen atom, or an unsubstituted or substituted C1-6 alkyl group.
  • R 1 is preferably a C1-6 haloalkyl group.
  • X 0 is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group Represents an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
  • m1 represents the number of substitutions of X 0 and is an integer from 0 to 3. When m1 is 2 or more, X 0 each other may be the same or different from each other.
  • halogen atom in 0, C2 having "unsubstituted or C1 ⁇ 6 alkyl group having a substituent", "C2 ⁇ 6 alkenyl groups having an unsubstituted or substituted group”, "unsubstituted or substituted Examples of the “ ⁇ 6 alkynyl group” and the “unsubstituted or substituted C1-6 alkoxy group” include those exemplified in the above X.
  • R 11 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted amino group, or an unsubstituted or substituted group
  • C1-6 alkyl group having a substituent in addition to those exemplified in the above X, a formylaminomethyl group, an acetylaminomethyl group, a 2-acetylaminoethyl group, a propionylaminomethyl group, a propionylamino group
  • a formylaminomethyl group such as a methyl group
  • Examples of the “substituted amino group” in R 11 include a C1-6 alkylamino group such as a methylamino group, an ethylamino group, and a dimethylamino group; a C2-6 alkenylamino group such as a vinylamino group and an allylamino group; And N′-substituted hydrazino groups such as a hydrazino group, an N ′, N′-dimethylhydrazino group, and an N′-methylenehydrazino group.
  • C1-6 alkylaminocarbonyl group examples include a methylaminocarbonyl group, ethylaminocarbonyl group, n-propylaminocarbonyl group and the like.
  • substituted C1-6 alkylaminocarbonyl group examples include a C1-6 haloalkylaminocarbonyl group such as a trifluoromethylaminocarbonyl group or a 2,2,2-trifluoroethylaminocarbonyl group; C1-6 alkoxy C1-6 alkylaminocarbonyl groups such as aminocarbonyl group and methoxyethylaminocarbonyl group; heteroaryl group substitution C1-6 such as pyridylmethylaminocarbonyl group, pyridylethylaminocarbonyl, pyrimidylmethylaminocarbonyl group Alkylaminocarbonyl group; and the like.
  • R 12 represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C1-6 alkoxy group, or a halogen atom. Show. “Unsubstituted or substituted C1-6 alkyl group”, “Unsubstituted or substituted C2-6 alkenyl group”, “Unsubstituted or substituted C1-6 alkoxy group” in R 12 , And “halogen atom” may be the same as those exemplified in X above.
  • R 11 and R 12 are connected, closed together with the carbon atoms to which they are attached a hydrocarbon ring of 5 to 8-membered ring having a substituent R 20, or, the substituents R 20 And a 5- to 8-membered heterocycle containing at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom may be formed.
  • R 20 represents a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group An unsubstituted or substituted C1-6 alkoxy group, a nitro group, a cyano group; an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group , An amino group, or a substituent represented by —N (R 2 ) COR 3 .
  • a C5-8 cycloalkene ring such as a cyclopentene ring or a cycloheptane ring
  • a C6-8 aryl ring such as a benzene ring
  • heterocyclic rings such as a dihydrofuran ring, a pyrrole ring, a pyrazole ring, and a 3,4-dihydro-2H-pyran ring;
  • Halogen atom in R 20, with the "unsubstituted or C1 ⁇ 6 alkyl group having a substituent", "C2 ⁇ 6 alkenyl groups having an unsubstituted or substituted group”, "unsubstituted or substituted C2
  • Examples of the “ ⁇ 6 alkynyl group” and the “unsubstituted or substituted C1-6 alkoxy group” include those exemplified in the above X.
  • Examples of the “unsubstituted or substituted C1-6 alkylaminocarbonyl group” for R 20 include the same groups as those exemplified for R 11 above.
  • Examples of the “C1-7 acyl group” in R 20 include formyl group, acetyl group, propionyl group, benzoyl group and the like.
  • Examples of the “substituted C1-7 acyl group” in R 20 include halogen-substituted C1-7 acyl groups such as a chloroacetyl group, a trifluoroacetyl group, a trichloroacetyl group, and a 4-chlorobenzoyl group. .
  • R 2 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-7 acyl group, or an unsubstituted or substituted C1-6 alkoxycarbonyl group Indicates.
  • Examples of the “unsubstituted or substituted C1-6 alkyl group” for R 2 include the same as those exemplified for X above.
  • Examples of the “unsubstituted or substituted C1-7 acyl group” in R 2 include the same as those exemplified for R 20 above.
  • Examples of the “C1-6 alkoxycarbonyl group” for R 2 include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and the like.
  • Examples of the “substituted C1-6 alkoxycarbonyl group” for R 2 include a cyclopropylmethoxycarbonyl group, a cyclobutylmethoxycarbonyl group, a cyclopentylmethoxycarbonyl group, a cyclohexylmethoxycarbonyl group, a 2-methylcyclopropylmethoxycarbonyl group, 2 , 3-dimethylcyclopropylmethoxycarbonyl group, 2-chlorocyclopropylmethoxycarbonyl group, 2-cyclopropylethoxycarbonyl group and the like C3-8 cycloalkyl C1-6 alkoxycarbonyl group; fluoromethoxycarbonyl group, chloromethoxycarbonyl group, Bromomethoxycarbonyl group, difluoromethoxycarbonyl group, dichloromethoxycarbonyl group, dibromomethoxycarbonyl group, trifluoromethoxycarbonyl group Trichloromethoxycarbon
  • R 3 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, A substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C2-6 alkenyloxy group, an unsubstituted or substituted group; And a C2-6 alkynyloxy group having an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heterocyclic group.
  • Examples of the “C3-8 cycloalkyl group” in R 3 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like.
  • Examples of the “substituted C3-8 cycloalkyl group” for R 3 include a chlorocyclohexyl group, a bromocyclohexyl group, a 2-methylcyclopropyl group, and a 2,3-dimethylcyclopropyl group.
  • Examples of the “C2-6 alkenyloxy group” in R 3 include a vinyloxy group, a 1-propenyloxy group, a 2-propenyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, a 3-butenyloxy group, and a 1-methyl-2- Propenyloxy group, 2-methyl-2-propenyloxy group, 1-pentenyloxy group, 2-pentenyloxy group, 1-methyl-2-butenyloxy group, 2-methyl-2-butenyloxy group, 1-hexenyloxy group, Examples include 2-hexenyloxy group.
  • Examples of the “substituted C2-6 alkenyloxy group” in R 3 include C2-6 haloalkenyloxy groups such as 2-chloro-1-propenyloxy group, 2-fluoro-1-butenyloxy group; .
  • Examples of the “C2-6 alkynyloxy group” in R 3 include ethynyloxy group, 1-propynyloxy group, 2-propynyloxy group, 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-methyl-2 -Propynyloxy group, 2-methyl-3-butynyloxy group, 1-pentynyloxy group, 2-pentynyloxy group, 1-methyl-2-butynyloxy group, 2-methyl-3-pentynyloxy group, 1- Examples include hexynyloxy group.
  • Examples of the “substituted C2-6 alkynyloxy group” for R 3 include a 4,4-dichloro-1-butynyloxy group, a 4-fluoro-1-pentynyloxy group, and a 5-bromo-2-pentynyloxy group.
  • C2-6 haloalkynyloxy groups such as and the like;
  • the “C6-10 aryl group” in R 3 may be monocyclic or polycyclic. In the polycyclic aryl group, as long as at least one ring is an aromatic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the C6-10 aryl group include a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, and a tetralinyl group.
  • the “heterocyclic group” in R 3 includes 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom as atoms constituting the ring.
  • the heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic group include a 5-membered heteroaryl group, a 6-membered heteroaryl group, a condensed heteroaryl group, a saturated heterocyclic group, and a partially unsaturated heterocyclic group.
  • 5-membered heteroaryl groups include: pyrrolyl groups such as pyrrol-1-yl, pyrrol-2-yl, and pyrrol-3-yl; furyl groups such as furan-2-yl and furan-3-yl ; Thienyl groups such as thiophen-2-yl group and thiophen-3-yl group; imidazolyl groups such as imidazol-1-yl group, imidazol-2-yl group, imidazol-4-yl group and imidazol-5-yl group A pyrazolyl group such as a pyrazol-1-yl group, a pyrazol-3-yl group, a pyrazol-4-yl group, a pyrazol-5-yl group; an oxazol-2-yl group, an oxazol-4-yl group, an oxazole-5 -Oxazolyl groups such as yl groups; isoxazol-3-yl groups, isox
  • the 6-membered heteroaryl group includes pyridyl groups such as pyridin-2-yl group, pyridin-3-yl group and pyridin-4-yl group; pyrazinyl groups such as pyrazin-2-yl group and pyrazin-3-yl group A pyrimidinyl group such as a pyrimidin-2-yl group, a pyrimidin-4-yl group and a pyrimidin-5-yl group; a pyridazinyl group such as a pyridazin-3-yl group and a pyridazin-4-yl group; a triazinyl group; It is done.
  • heterocyclic groups include: aziridin-1-yl group, aziridin-2-yl group, epoxy group; pyrrolidin-1-yl group, pyrrolidin-2-yl group, pyrrolidin-3-yl group, tetrahydrofuran-2- Yl group, tetrahydrofuran-3-yl group; piperidin-1-yl group, piperidin-2-yl group, piperidin-3-yl group, piperidin-4-yl group, piperazin-1-yl group, piperazin-2-yl Group, morpholin-2-yl group, morpholin-3-yl group, morpholin-4-yl group; 1,3-benzodioxol-4-yl group, 1,3-benzodioxol-5-yl group 1,4-benzodioxan-5-yl group, 1,4-benzodioxan-6-yl group, 3,4-dihydro-2H-1,5-benzodiox
  • R 3 is preferably a C1-6 alkyl group, a C1-6 alkoxy C1-6 alkyl group, or a C1-6 alkoxy C1-6 alkoxy C1-6 alkyl group.
  • (E) E represents a carbon atom or a nitrogen atom. Of these, E is preferably a carbon atom.
  • heterocyclic compound represented by formula (II) In the heterocyclic compound represented by the formula (II), in the formula (I), B 1 is a carbon atom, B 2 is a nitrogen atom, B 3 is an oxygen atom, and a bond between B 1 and B 2 is a double bond It is what has become. That is, the heterocyclic compound represented by the formula (II) has an isoxazoline ring (4,5-dihydroisoxazole ring). Furthermore, the heterocyclic compound represented by the formula (II) has a substituent R 21 in which R 11 and R 12 in the formula (I) are linked together with the carbon atom to which they are bonded.
  • D in the formula (II) represents a 5- to 8-membered hydrocarbon ring or a 5- to 8-membered heterocycle containing at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom.
  • R 21 is a substituent bonded to D and is an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkylaminocarbonyl group, an amino group, or —N ( R 2 ) represents a substituent represented by COR 3 .
  • X 1 is a substituent bonded to the condensed ring containing D and is a halogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, unsubstituted Or a substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
  • m represents the number of substitutions of X 1 and is an integer from 0 to 6. When m is 2 or more, X 1 may be the same as or different from each other.
  • Heterocyclic compound represented by formula (III) In the heterocyclic compound represented by the formula (III), D is a 5- or 6-membered hydrocarbon ring in the formula (II), and R 21 is a substituent represented by —N (R 2 ) COR 3. It is what has become. That is, p represents the number of repeating methylene groups in parentheses and is either 1 or 2. p is preferably 1. That is, the heterocyclic compound represented by the formula (III) preferably has an indane ring (also known as a 2,3-dihydroindene ring).
  • X, n, A 1 , A 2 , R 1 , X 1 , m, R 2 , R 3 and E in formula (III) have the same meaning as in formula (II).
  • Heterocyclic compound represented by formula (IV) The heterocyclic compound represented by the formula (IV) is one in which both A 1 and A 2 in the formula (III) are carbon atoms.
  • X, n, R 1 , X 1 , m, E, R 2 , R 3 and p in formula (IV) have the same meaning as in formula (III).
  • the salt of the heterocyclic compound represented by the formula (I) to the formula (IV) is not particularly limited as long as it is veterinary acceptable, but such as hydrochloride, nitrate, sulfate, phosphate, etc. And salts of inorganic acids; salts of organic acids such as acetate, lactate, propionate and benzoate.
  • Heterocyclic compounds represented by the formulas (I) to (IV) or salts thereof are produced by referring to the methods described in Patent Document 3, Patent Document 4, Patent Document 5, Patent Document 6, and the like. Or you can get it.
  • the compound represented by the formula (II) can be produced by the method shown below.
  • the compound represented by the formula (2) is obtained by allowing a halogenating agent to act on the compound represented by the formula (1).
  • the halogenating agent is not particularly limited, and N-halogenosuccinic imides, alkali metal hypohalites, hypohalites, carrier halogens and the like can be used.
  • the amount of the halogenating agent to be used is generally 1 to 10 equivalents relative to the compound represented by the formula (1).
  • This reaction is preferably carried out in a solvent.
  • the solvent to be used is not particularly limited as long as it is inert to the reaction.
  • aromatic hydrocarbons such as benzene, aliphatic hydrocarbons such as hexane, alicyclic hydrocarbons such as cyclohexane, chlorobenzene, and the like.
  • Aromatic halogenated hydrocarbons such as dichloromethane, aliphatic halogenated hydrocarbons such as dichloromethane, ethers such as diethyl ether, esters such as ethyl acetate, amides such as N, N-dimethylformamide, alcohols such as methanol , Carboxylic acids such as acetic acid, acetonitrile, water and the like may be used alone or in admixture of two or more.
  • the reaction temperature is not limited, but is usually in the temperature range from ⁇ 60 ° C. to the reflux temperature of the reaction mixture.
  • the compound represented by the formula (2) thus obtained can usually be subjected to the next reaction without isolation.
  • the compound represented by the formula (II) can be obtained by allowing the compound represented by the formula (3) to act. it can.
  • the base to be used is not particularly limited, and examples thereof include alkali metal hydroxides such as sodium hydroxide, alkali metal carbonates such as sodium carbonate, alkali metal bicarbonates such as sodium bicarbonate, and organic bases such as triethylamine.
  • the amount of the base used is usually 1 to 5 equivalents relative to the compound represented by the formula (2). This reaction is preferably carried out in a solvent.
  • the solvent to be used is not particularly limited as long as it is inert to the reaction.
  • the same solvent as used in the reaction for obtaining the compound represented by the formula (2) can be used.
  • the reaction temperature is not limited, but is usually in the temperature range from ⁇ 60 ° C. to the reflux temperature of the reaction mixture.
  • the salts of the heterocyclic compounds represented by the formulas (I) to (IV) can be obtained, for example, by reacting the heterocyclic compounds represented by the formulas (I) to (IV) with an inorganic acid or an organic acid. Can be manufactured.
  • any reaction after completion of the reaction, it can be purified by a purification means such as distillation, recrystallization or column chromatography, if necessary, after a usual post-treatment operation.
  • a purification means such as distillation, recrystallization or column chromatography, if necessary, after a usual post-treatment operation.
  • the structure of the target product can be identified and confirmed by analytical means such as elemental analysis, NMR spectrum, IR spectrum, and mass spectrum.
  • the animal ectoparasite control agent of the present invention may contain components other than the above active ingredients. For example, various vitamins, minerals, hormones, amino acids, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, anticancer agents, antibiotics, endoparasite control agents, antibacterial agents, bactericides, coloring agents, fragrances , Preservatives, vaccines and the like. Further, it may contain a compound having biological activity such as insecticidal, acaricidal, anthelmintic, fungicidal, nematicidal, antiprotozoal, bactericidal and antiviral.
  • the animal ectoparasite control agent of the present invention is not particularly limited by the dosage form.
  • the dosage form include powders, granules, tablets, powders, capsules, premixes, solutions, emulsions, suspensions, wafers, biscuits, minced meat and the like.
  • the animal ectoparasite control agent of the present invention contains a carrier such as a liquid carrier, a gaseous carrier, a solid carrier, etc., depending on the dosage form, and if necessary, contains a surfactant and other auxiliary agents for use. You may formulate according to it. Further, the animal ectoparasite control agent of the present invention may be obtained by impregnating a base material such as a porous ceramic plate or a nonwoven fabric with an active ingredient.
  • Liquid carriers used in formulating liquid preparations include kerosene, xylene; petroleum fractions such as solvent naphtha; cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, NMP, alcohol, acetone, methyl isobutyl ketone, mineral oil , Vegetable oil, water and the like.
  • gaseous carrier used in formulating a propellant include butane gas, LPG, dimethyl ether, carbon dioxide gas and the like.
  • Solid carriers used when formulating into solid formulations include lactose, sucrose, glucose, starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, soybean powder, wheat flour and other vegetable powders; other commercially available feed ingredients Mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, and clay; organic and inorganic compounds such as calcium carbonate, sodium benzoate, urea, and mirabilite.
  • Adjuncts used in formulating poison baits include food ingredients such as cereal flour, vegetable oil, sugar and crystalline cellulose, antioxidants such as dibutylhydroxytoluene, preservatives such as dehydroacetic acid, children such as pepper Pest-attracting fragrances such as anti-fouling agents for pets, cheese fragrances, and onion fragrances.
  • a surfactant can be added so that a uniform and stable form can be obtained in formulation.
  • Non-ionic surfactants such as alkyl ethers added with polyoxyethylene, higher fatty acid esters added with polyoxyethylene, sorbitan higher fatty acid esters added with polyoxyethylene, and tristyryl phenyl ether added with polyoxyethylene
  • Surfactants sulfates of alkylphenyl ethers with addition of polyoxyethylene, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, isobutylene-maleic anhydride And the like.
  • pour-on or spot-on formulations are suitably carriers that facilitate rapid dispersion on the skin surface of the host animal or in the fur and are generally considered as spreading agents Containing.
  • Preferred carriers are, for example, alcohols such as isopropanol, 2-octyldodecanol, oleyl alcohol, benzyl alcohol; glycols such as diethylene glycol, ethyl carbitol; isopropyl myristate, isopropyl palmitate, decyl oleate, hexyl laurate , Long chain fatty acid esters such as oleyl oleate, decyl oleate, capric acid ester of C12-18 alkanol; dicarboxylic acid esters such as dibutyl phthalate, diisopropyl isophthalate, diisopropyl adipate, di-n-butyl adipate And cyclic amides such as pyrroli
  • the animal ectoparasite control agent of the present invention can be administered to an animal alone.
  • other animal drugs such as antibacterial agents, nutrients, anthelmintics, fungicides, anticoccidial agents, insecticides, acaricides, fungicides, nematicides, antiprotozoal agents, antiviral agents It can be administered together with vaccines, hormonal agents, anticancer agents, antibiotics, antipyretics, sedatives, anti-inflammatory agents, endoparasite control agents, and the like.
  • animal drugs that can be mixed or used in combination with the animal ectoparasite control agent of the present invention are not particularly limited. For example, the following are mentioned.
  • Organic (thio) phosphates acephate, azamethiphos, azinephos methyl, azinephos ethyl, bromophos ethyl, bromfenbinphos, BRP, chlorpyrifos, chlorpyrifos methyl, chlorpyrifos ethyl, chlorfenvinphos, kazusafos, Carbophenothione, chloroethoxyphos, chlormefos, coumaphos, cyanophenphos, cyanophos, CYAP, diazinon, dichlorvos, dicrotophos, dimethoate, disulfotone, dimeton-S-methyl, dimethylvinphos, dimeton-S-methylsulfone, diariphos, diazinon , Diclofenthion, dioxabenzophos, disulfoton, ethion, etoprophos, etrimphos, E
  • Nicotine receptor agonist / antagonist compounds acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, nithiazine, nicotine, bensultap, cartap; (6) GABA antagonist compound: (A) acetoprole, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole; (B) Organic chlorine-based: camfechlor, chlordane, endosulfan, HCH, ⁇ -HCH, heptachlor, methoxychlor;
  • Macrocyclic lactone insecticides abamectin, emamectin benzoate, milbemectin, lepimectin, spinosad, ivermectin, selamectin, doramectin, epinomectin, moxidectin;
  • METI I compounds phenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, hydramethylnon, fenpyroximate, pyrimidifen, dicophor;
  • METI II and III compounds acequinosyl, fluacrylpyrim, rotenone;
  • Uncoupler compounds chlorfenapyr, binapacryl, dinobutone, dinocup, DNOC;
  • Oxidative phosphorylation inhibitor compounds cyhexatin, diafenthiuron, phenbutatin oxide, propargite, azocyclotin;
  • molting disrupting compound cyromazine;
  • Mixed function oxidase inhibitor compound piperonyl butoxide;
  • Sodium channel blocker compounds indoxacarb, metaflumizone;
  • Microbial pesticides BT agent, entomopathogenic virus agent, entomopathogenic fungus agent, nematode pathogenic fungus agent; Bacillus spp. Lilium species;
  • Latrophilin receptor agonist depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;
  • Octopaminergic agent Amitraz
  • Ryanodine derivative agonist fulbenzamide, chlorantraniliprole, cyantraliniprol
  • Inhibitors of magnesium-stimulated ATPase thiocyclam, thiosultap, nereistoxin
  • antifeedant pymetrozine
  • Tick growth inhibitor clofentezin, etoxazole
  • Others Benclothiaz, Bifenazate, Pyridalyl, Sulfur, Sienopyraphene, Ciflumethofene, Amidoflumet, Tetradiphone, Chlordimeform, 1,3-Dichloropropene, DCIP, Phenisobromolate, Benzomate, Metaaldehyde, Spinetram, Pyrifluquinazone, Benzo Ximate, bromopropyrate, quinomethionate, chlorbenzilate, chloropicrin, cloth
  • Anthelmintic (A) benzimidazole series: fenbendazole, albendazole, triclabendazole, oxybendazole; (B) Salicylanilide series: closantel, oxyclozanide; (C) substituted phenol type: nitroxinyl; (D) pyrimidine series: pyrantel; (E) imidazothiazole series: levamisole; (F) tetrahydropyrimidine: praziquantel; (G) Other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazo.
  • the use ratio of the animal ectoparasite control agent of the present invention to other animal drugs is not particularly limited, but is usually 100: 0 to 1:99 (weight ratio).
  • Examples of host animals in which the animal ectoparasite control agent of the present invention is effective include dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets; Cattle, horses, pigs, sheep, goats; poultry (eg, ducks, chickens, quails, geese); bees (eg, honey bees, Japanese honey bees);
  • ectoparasites that are targets of the animal ectoparasite control agent of the present invention, obtain nutrients such as blood and dandruff from animals that parasitize the back, armpit, lower abdomen, and inner crotch of the host animal. It includes those that inhabit, and those that fly to the back and buttocks of the host animal to obtain nutrients such as blood and dandruff from the animal. Examples of ectoparasites include ticks, lice and fleas.
  • mites Acari that are the targets of the control agent.
  • mite A) Dermanyssidae mites, for example, Dermanyssus gallinae from the genus Dermanyssus spp .;
  • mites of the family Mronyssidae for example, Ornithonyssus spp., Ornithonyssus sylviarum, Ornithonyssus bursa, Ornithonyssus bacoti;
  • C Mites of the family Laelapidae, for example Laelaps echidninus, Laelaps jettmari, Tropilaelaps clarae of the species of the genus Laelaps spp .;
  • Varroidae mites for example, Varroa spp., Varroa destructor, V
  • Astigmata (Acaridida)
  • A Mites of the family Psoroptidae (Psoroptidae), for example Psoroptidae spp., Psoroptes ovis, rabbits Psoroptes cuniculi, Psoroptes equi; Psoroptes equi Chorioptes spp., Chorioptes bovis; Otodectes spp., Otodectes cynotis;
  • B Scaroptidae mites, for example, Sarcoptes spabi., Sarcoptes canis, Sarcoptes bovis, Sarcoptes spis.
  • Prostigmata mites Actinedida
  • A Acaridaceae (Demodixidae) mites, for example, Demodex spp., Demodex canis, Demodex bovis, Demodex ovis, Demodex ovis, Demodex caprae, Democratic mites (Demodex equi), Demodex caballi (Demodex caballi), Scarlet mites (Demodex suis), Caterpillar mites (Demodex cati);
  • B Trombiculidae ticks, for example, Troombicula spp., Trombicula alfreddugesi, Trombicula akamushi;
  • Examples of lice include the following pests.
  • Louse of Anoplura (A) lice of the family Haematopinidae, such as the Haematopinus asini, the Haematopinus eurysternus, the Haematopinus suis of the Haematopinus spp .; (B) Linognathidae lice, for example, Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus ovillus, Linognathus ovillus Linognathus pedalis, Linognathus stenopsis; for example, Solenopotes spp., Solenopotes capillatus;
  • Amblycera subs (A) Mennoponidae larvae, for example, Menacanthus stramineus, Menacanthus cornutus, Menacanthus cornutus, Menacanthus cornutus, Menacanthus corp. Chick gallinae of the genus species (Menopon spp.);
  • Ischnocera Biting louse: (A) Philopteridae lice, for example, Columbicola spp., Columbicola columbae; for example, Cuclotogaster spp., Cuclotogaster spp. heterographus); eg, Goniodes spp., Goniodes dissimilis, Goniodes gigas, Goniodes gallinae; eg, Lipeurus spp.
  • Trichodectidae such as Bovicola spp., Bovicola bovis, Bovicola ovis, Bovicola limbata, Bovicola e, Bovicola capra Boccola equi; for example, Trichodectes canis of Trichodectes spp .; for example, Felicola subrostrata of Felicola spp.
  • the fleas include the following pests.
  • A fleas from the family Tungidae, for example from the genus Tunga spp., Tunga penetrans
  • B Pulicidae fleas, for example, Ctenocephalides canis, Fleas of Ctenocephalides felis; for example, Hedgehog );
  • Xenopsylla spp. For example, Xenopsylla cheopis; for example, for Pulex irritans; Flea (Echidnophaga gallinacea);
  • C fleas of the family Ceratophyllidae, for example Ceratophyllus gallinae, Ceratophyllus anisus, for example Ceratophyllus anisus; for example, Nosopsyllus spp. (Nosopsyllus fasciatus),
  • D Fleas of the family Leptopsyllidae, for example,
  • insects of the order of the Hemiptera insects of the family Cimicidae, for example Cimex lectularius, of the genus Cimex spp .;
  • insects of the family Cimicidae for example Cimex lectularius, of the genus Cimex spp .
  • Insects of Reduviidae and also of Triatominae, for example Panstrongylus spp .
  • Rhodnius spp. Rhodnius prolixus
  • the ectoparasite-controlling agent of the present invention is also effective against insect pests (Diptera) that are biting insects (chewing flies, adult sucking flies, migratory dipterous larvae, parasitic fly maggots) It is.
  • insect pests Biting insects (chewing flies, adult sucking flies, migratory dipterous larvae, parasitic fly maggots) It is.
  • the following pests can be mentioned as pests of flies (Diptera).
  • Nematocera (A) Culicidae mosquitoes, such as Culex spp., Culex quinquefasciatus, Culex pipiens pallens, Culex tarsalis, Culex pipiens molestus , Culex pipiens fatigans, Culex tritaeniorhynchus summorosus; eg, Armigeres subalbatus; eg, Anopheles spp. Ele, g.
  • Simuliidae such as Simulium spp., Simulium reptans, Simulium ornatum, Simulium venustum, Simulium salopiense
  • Prosimulium spp Prosimulium yezoense
  • C Ceratopogonidae, such as the Culiodes spp., Culicoides arakawae, Culicoides pictimargo, Culicoides kibunensis, musul, C oxystoma), Nipponukaka
  • Muscidae flies such as Muscina spp., Musca domestica, Musca bezzii, Musca hervei, Musca conducens, Musca conducens Musca stabulans); for example, Stomoxys spp., For Stomoxys calcitrans; , Haematobia stimulans; Fannia spis., Fannia canisularis;
  • C Glossina spp.
  • Hypoderma bovis Hypoderma lineatum; for example, Gasterophilus spp., Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gastrophilus Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum; eg from the Oestrinae family, and also from the genus Oestrus spp. Oestrus ovis).
  • fleas and ticks are preferred as the target of the animal ectoparasite control agent of the present invention.
  • the animal ectoparasite control agent of the present invention is administered to an animal, and the above ectoparasites are suppressed, thereby partially or completely inhibiting the occurrence of parasitic diseases in animals susceptible to parasitic diseases. Can reduce or eliminate disease symptoms and partially or completely cure and treat parasitic diseases.
  • Diseases transmitted through ectoparasites are, for example, bacterial diseases, viral diseases, and protozoan-borne diseases. Like flies, there are those that cause pathogens to adhere to sticky legs and transport them to other places, and those that develop and multiply in the body of sanitary pests, which become the source of infection. Specific examples are given below.
  • Viral diseases (a) Akabane disease infected by Culicoides oxystoma via Akabane virus of Bunyaviridae; Ainovirus infection infected via Aino virus Infectious disease: Ibaraki disease infecting via Reoviridae Ibaraki virus; Chuzan disease infecting via Chuzan virus; Via Bluetongue virus of Orbivirus Bluetongue disease to infect; Arbos that are transmitted through other arboviruses such as Peaton virus, Sathuperi virus, D'Aguilar virus and Shamonda virus Viral disease; (B) Porcine cholera which Culex quinquefasciatus infects via swine cholera virus of Flaviviridae; (C) Japanese encephalitis infected by Culex tritaeniorhynchus summorosus and Culex pipiens pallens via Japanese encephalitis virus of Flaviviridae; (D) Avian Newcastle
  • Bacterial diseases (a) Japanese red fever, rickettsia, etc. in dogs infected with Haemaphysalis longicornis via Japanese Rickettsia spp, Rickettsia japonica; (B) Barbarian disease infected by the tick (Haemaphysalis flava) via the wild moss (Francisella tularensis); (C) Cat infectious anemia which is transmitted by Candidatus Mycoplasma haemominutum by Ixodes ovatus; (D) Anaplasmosis in which a tick (Rhipicephalus (Boophilus) microplus) is infected via Anaplasma marginale; (E) Canine anaplasmosis infected via Anaplasma platys by Rhipicephalus sanguineus; Canine hemobartonellosis infected via Haemobartonella canis.
  • a Japanese red fever, rickettsia, etc.
  • Protozoan-borne disease Cattle large piroplasmosis infected by Haemaphysalis longicornis through large piroplasma (Babesia ovata); Dogs infected through Gibson dog Babesia (Babesia gibsoni) Piroplasmosis;
  • B Babesiosis, such as bovine Q fever, infected by the tick (Rhipicephalus (Boophilus) microplus) through Futago Babesia (Babesia bigemia), Bovine Babesia (Babesia bovis);
  • C Canine babesiosis infected via Rabicephalus sanguineus via the canine Babesia, Gibson dog Babesia; the canine infecting the canine hepatozoon canis Hepatozonosis;
  • D chicken leucocytozoonosis in which chickens (Culicoides arakawae) are
  • hygienic pests are internally parasitic on the host. For example, cattle fly larvae infested with cows, horsefly larvae in the stomach wall of horses, and sheep fly larvae in the nasal cavity of sheep. In addition, cattle fly larvae parasitize under the back of cattle and make holes in the skin, greatly reducing the value of leather products. Specific examples are given below.
  • A Cattle fly larvae caused by Hypoderma bovis larvae, Hypoderma lineatum larvae;
  • B the larvae of Gasterophilus intestinalis, the larvae of the Gasterophilus nasalis, the larvae of the fountains caused by the larvae of the Atoll frog (Gasterophilus haemorroidalis);
  • C Flies (myiasis) caused by larvae of Lucilia illustris.
  • Injuries caused by parasitism or bites When a bite by a mite such as a mite or a claw mite, or an insect such as a mosquito, ab, or a lice, it causes severe itching or pain due to physical injury or injection of a poisonous substance, resulting in large damage to the host. Give stress. Furthermore, secondary infection is caused by the animal scratching the affected area. For this reason, animals suffer from insomnia and loss of appetite, and in livestock, milk production, body weight gain and egg production decline, production efficiency drops, and sometimes death. Specific examples are given below.
  • A Strong sense of sensation caused by cattle flies (Stomoxys calcitrans) and flies (Haematobia irritans);
  • B Strong sensation caused by pig lice (Haematopinus suis) in pigs;
  • C The sensation caused by dog fleas (Ctenocephalides canis) in dogs and cats;
  • D The sensation caused by chicken hawk (Culicoides arakawae); The strong sensation caused by chicken lice (Menopon gallinae).
  • A cattle, horses, sheep scabies caused by genus genus genus, genus cuspidaceae; pigs, canine scabies caused by genus genus genus; cat scabies caused by cat genus genus; , Cat ear scabies;
  • B flea allergic dermatitis caused by a cat flea;
  • C folliculosis caused by acarid mites;
  • D Papules, blisters, and edema caused by flyfish.
  • the animal ectoparasite control agent of the present invention When used for domestic animals such as cattle and pigs, pets such as dogs and cats, it varies depending on the administration method, administration purpose, disease symptoms, etc.
  • the ratio is 0.01 mg or more and 100 g or less, desirably 0.1 mg or more and 10 g or less, per 1 kg body weight of the host animal.
  • the animal ectoparasite control agent of the present invention can be applied by a known veterinary technique (topical, oral, parenteral or subcutaneous administration).
  • a known veterinary technique topical, oral, parenteral or subcutaneous administration
  • tablets, capsules, soaking solution, feed mixing, suppositories, injection injection (intramuscular, subcutaneous, intravenous, abdominal cavity)
  • injection injection
  • non-systemic control the oily or aqueous solution is administered by spraying, pour-on, spot-on, etc., resin And the like, and kneading an ectoparasite control agent, forming the kneaded product into an appropriate shape such as a collar and an ear tag, and attaching it to an animal.
  • oral administration such as buccal administration and sublingual administration, or parenteral administration such as intravenous administration, intramuscular administration, subcutaneous administration, transdermal administration, nasal administration, and pulmonary administration are performed.
  • oral administration include a method of feeding an animal with the control agent of the present invention in the form of tablets, liquids, capsules, wafers, biscuits, minced meat, etc .; mixing the control agent of the present invention into animal feed Let me give it to the animal.
  • parenteral administration include intramuscular, intradermal, subcutaneous injection or infusion; spot-on, po-on, etc .; spray, shampoo, etc .; The method of attaching it to an animal is mentioned.
  • the pharmaceutical formulation of the animal drug ectoparasite control agent of the present invention is shown slightly, but the additives and addition ratios are not limited to these descriptions, and can be varied in a wide range.
  • the part in a formulation example shows a weight part (%). The following are prescriptions for prevention and control of animals.
  • Formulation 1 (granule) Compound of the present invention 5% Kaolin 94% 1% white carbon
  • the compound of the present invention is dissolved in an organic solvent, sprayed onto a carrier, and then the solvent is evaporated under reduced pressure. This type of granule can be mixed with animal food.
  • Formulation 2 (granule) Compound of the present invention 10% Attapulgite 90%
  • Formulation 3 (Granule) Compound of the present invention 3% Polyethylene glycol 3% Kaolin 94% Kaolin previously wetted with polyethylene glycol and a finely pulverized product of the compound of the present invention are mixed to obtain a preparation having the granule surface coated with the compound of the present invention.
  • Formulation 4 (Injection) Compound of the present invention 0.1-1% Peanut oil Balance After preparation, filter sterilize with a sterilization filter.
  • Formulation 5 (Injection) Compound of the present invention 0.1-1% Sesame oil balance
  • Formulation 6 (Pour-on agent) Compound of the present invention 5% Myristic acid ester 10% Isopropanol balance
  • Formulation 7 (Pour-on agent) The compound of the present invention 2% Medium chain triglycerides 15% Ethanol balance
  • Formulation 8 (Pour-on agent) The compound of the present invention 2% Oleic acid ester 5% NMP 40% Isopropanol balance
  • Formulation 10 Compound of the present invention 10-15% Palmitic acid ester 10% Isopropanol balance
  • Formulation 11 Compound of the present invention 10-15% Isopropanol 20% Benzyl alcohol balance
  • Formulation 12 (spray-on agent) Compound of the present invention 1% Isopropanol 40% Propylene carbonate balance
  • Formulation 13 (spray-on agent) Compound of the present invention 1% Propylene glycol 10% Isopropanol balance
  • Test Example 1 Insecticidal test against Haemaphysalis longicornis 0.1175 ml of an acetone solution having an active ingredient concentration of 400 ppm was applied to the inner wall of a 20 mL glass vial. Acetone was volatilized to produce a thin film on the inner wall of the vial. Since the surface area of the inner wall of the used vial is 47 cm 2 , the treatment drug amount is 1 ⁇ g / cm 2 . Twenty to fifty ticks of the spider mite were released into the vial, and the lid was closed and housed in a thermostatic chamber (25 ° C., dark). The number of dead insects was counted after 1 day and after 2 days, and the death rate was calculated from the following formula.
  • test was conducted in a two-run system. Further, in a similar manner, the application dose, 0.1 ⁇ g / cm 2, 0.01 ⁇ g / cm 2, 0.001 ⁇ g / cm 2, and 0.0001 / cm 2, even test was changed to Been.
  • the animal ectoparasite control agent according to the present invention containing Compound 1-1 or Compound 1-2 as an active ingredient is more effective against ectoparasites than the control agent containing the existing compound fipronil. It turns out that it is excellent in immediate effect and low concentration activity.
  • Test Example 2 Insecticidal test (immersion) against Boophilus microplus 10 mg of the active ingredient was dissolved in 0.5 mL of dimethyl sulfoxide. This solution was diluted with water to obtain an aqueous solution adjusted to a predetermined concentration. In a perforated plastic beaker, 8 to 10 adult females of the tick were fed, and the beaker was immersed in the aqueous solution for 1 minute. The mites dipped in the aqueous solution were transferred onto the filter paper laid on the plastic tray. After a certain period, tick mortality was calculated. A mortality rate of 100% means that all ticks have died. A mortality rate of 0% means that all mites have survived.
  • Test Example 3 Insecticidal test for Boophilus microplus (injection) 10 mg of the active ingredient was dissolved in 0.5 mL of dimethyl sulfoxide. This solution was diluted with water to obtain an aqueous solution adjusted to a predetermined concentration. The above aqueous solution was injected into the abdomen of 15 adult females of mites that were completely fed. Mites were transferred to replication plates and incubated for a period of time in a climate chamber. After a certain period of time, the egg-laying rate of infertile eggs was measured. 100% means that all eggs are sterilized eggs. 0% means that all eggs are fertilized eggs.
  • Test Example 4 Insecticidal test against Rhipicephalus sanguineus (contact) The active ingredient was dissolved in acetone to prepare an acetone solution having a concentration of 900 ppm. 250 ⁇ L of an acetone solution diluted to a specified concentration was poured into a glass vial, the vial was fixed to a lock-type roller, rotated at 10 rpm, and acetone was volatilized over 2 hours. Five adult ticks that were cut off were placed in the vial, and the vial was covered with a perforated cover. After 2 days, tick mortality was measured. A mortality rate of 100% means that all ticks have died. A mortality rate of 0% means that all mites have survived.
  • Test Example 5 Insecticidal test against cat flea (Ctenocephalides felis) The active ingredient was dissolved in acetone to prepare an acetone solution having a concentration of 900 ppm. 250 ⁇ L of an acetone solution diluted to a specified concentration was poured into a glass vial, the vial was fixed to a lock-type roller, rotated at 10 rpm, and acetone was volatilized over 2 hours. Ten adult cat fleas that were cut off were placed in the vial, and the vial was covered with a perforated cover. After 2 days, flea mortality was measured. A mortality rate of 100% means that all the fleas have died. A mortality rate of 0% means that all fleas have survived.
  • Test Example 6 Insecticidal test against cat flea (Ctenocephalides felis) (oral) 10 mg of the active ingredient was dissolved in 0.5 mL of dimethyl sulfoxide. This solution was diluted with livestock blood to prepare a compound solution with a specified concentration. About 10-15 adult fasted cat fleas were placed in a flea chamber. The bottom of the blood chamber was sealed with parafilm. The compound solution was filled into the blood chamber. Cat fleas can suck blood through paraffin. The blood chamber was kept at 37 ° C. and the flea chamber was kept at room temperature. After a certain period of time, cat mortality was measured. A mortality rate of 100% means that all cat fleas have died. A mortality rate of 0% means that all cat fleas have survived.
  • Test Example 7 Test on sheep flies (Lucillia cuprina) 10 mg of active ingredient was dissolved in 0.5 mL of dimethyl sulfoxide. This solution was diluted with water to obtain an aqueous solution having a predetermined concentration. A test tube was charged with 1 cm 3 of ground horse meat and 0.5 mL of the above aqueous solution. About 20-30 sheep larvae were placed on this. After a certain period of time, fly mortality was measured. A mortality rate of 100% means that all flies have died. A mortality rate of 0% means that all flies have survived.
  • Test Example 8 Test on Housefly (Musca domestica) 10 mg of the active ingredient was dissolved in 0.5 mL of dimethyl sulfoxide. This solution was diluted with water to obtain an aqueous solution having a predetermined concentration. 0.3 ml of the aqueous solution was mixed with 0.2 ml of 40% by weight sugar aqueous solution. This mixed solution was absorbed into a sponge of a predetermined size. A sponge was placed in the test container. Ten adult house flies were released into the test container and the container was covered with a perforated cover. After a certain period of time, fly mortality was measured. A mortality rate of 100% means that all flies have died. A mortality rate of 0% means that all flies have survived.
  • Test Example 9 Test for Cat Fleas in Cats (Ctenocephalides felis) A drug solution prepared to have an active ingredient of 15 mg per kg body weight of cats was dropped onto the skin behind the neck of the cat (between the scapulae). Six such cats were prepared. One day after the chemical treatment, 7 non-fed adult cat fleas per cat were infested around the neck of the cat. The number of surviving cat fleas was counted one day after the day of infestation. Six days after the chemical treatment, 7 non-feeding adult cat fleas per cat were infested around the neck of the cat. The number of surviving cat fleas was counted one day after the day of infestation. Similarly, cat flea infestation was performed after 13 days, 20 days, 27 days, 34 days, 41 days, and 48 days after the chemical treatment, and 1 day from the day of infestation. Later, the number of surviving cat fleas was counted.
  • Test Example 10 Test on tick (Ixodes ricinus) in cats Five non-feeding adult ticks per cat were infested around the neck of the cat. Six such cats were prepared. Two days after the day of infestation, a drug solution prepared so that the active ingredient was 15 mg per kg body weight of the cat was dropped on the skin behind the neck of the cat (between the scapula). The number of surviving ticks was counted two days after the chemical treatment. Five days after the chemical treatment, 5 non-feeding adult ticks per cat were infested around the neck of the cat. The number of surviving ticks was counted after 2 days from the day of infestation. Similarly, tick infestation was performed after 12 days, 19 days, 26 days, and 33 days from the day of chemical treatment, and after 2 days from the day of infestation, The number was measured.
  • a mortality rate of 100% means that all ticks have died.
  • a mortality rate of 0% means that all ticks have survived.
  • the above test was conducted using compounds 1-1, 1-4, 1-5, 1-8 and 1-9 shown in Table 1 as active ingredients. All the compounds showed excellent activity with a mortality rate of 90% or more as measured after 14 days from the day of chemical treatment. Compound 1-8 was measured 21 days after the chemical treatment, compound 1-9 was measured 28 days after the chemical treatment, and compounds 1-1 and 1-5 were treated with chemical. Even after 35 days from the date of measurement, the activity was particularly excellent with a mortality rate of 90% or more.
  • the ectoparasite control agent for animals of the present invention can control ectoparasites such as ticks from animals with high effects, has a long duration of effect, has a wide action spectrum, and is low in toxicity. There are few restrictions on mixed use.
  • By administering the animal ectoparasite control agent of the present invention to an animal it is possible to prevent the animal from suffering from an ectoparasite-derived infection.
  • An infectious disease can be treated by administering the animal ectoparasite control agent of the present invention to an animal suffering from an ectoparasite-derived infection.

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Abstract

La présente invention concerne un agent de lutte contre les ectoparasites étant très efficace dans la lutte contre les poux, les puces, les moustiques, les moucherons, les mouches et autres ectoparasites. Ledit agent contient, en tant qu'ingrédient actif, au moins un composé choisi parmi les composés hétérocycliques représentés par la formule (IV) ou une autre formule, et leurs sels. (Dans la formule (IV), X et X1 représentent des atomes d'halogène ou des groupes haloalkyle en C1-6 ou analogues ; R1 représente un groupe haloalkyle en C1-6 ou analogue ; R2 représente un atome d'hydrogène ou analogue ; R3 représente un groupe haloalkyle en C1-6 ou analogue ; n est un entier valant de 0 à 5, m est un entier valant de 0 à 6, E représente un atome de carbone ou un atome d'azote ; et p est un entier valant 1 ou 2.)
PCT/JP2011/075049 2010-11-04 2011-10-31 Agent de lutte contre les ectoparasites des animaux WO2012060317A1 (fr)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013087710A3 (fr) * 2011-12-14 2013-11-07 Syngenta Participations Ag Mélanges pesticides
WO2014039475A1 (fr) * 2012-09-07 2014-03-13 Zoetis Llc Combinaisons antiparasitaires d'isoxazoline spirocyclique
WO2014039422A1 (fr) * 2012-09-04 2014-03-13 Zoetis Llc Dérivés d'isoxazoline spirocyclique pour le traitement des poux de mer
US8735362B2 (en) 2009-12-01 2014-05-27 Syngenta Crop Protection, Llc Insecticidal compounds based on isoxazoline derivatives
JP2015003900A (ja) * 2013-05-23 2015-01-08 宮崎みどり製薬株式会社 ワクモ防除剤
US11034669B2 (en) 2018-11-30 2021-06-15 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof
WO2022003610A1 (fr) 2020-07-02 2022-01-06 Pi Industries Ltd. Dérivés de 2-(4,5-dihydroisoxazol-3-yl) isoindoline-5-carboxamide et composés similaires utilisés comme pesticides pour la protection des cultures
WO2023037253A1 (fr) 2021-09-08 2023-03-16 Pi Industries Ltd Composés d'isoxazoline et leur utilisation en tant qu'agents de lutte contre les nuisibles

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005085216A1 (fr) * 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. Composé benzamide substitué par de l’isoxazoline et agent de contrôle d’organisme nocif
JP2008110971A (ja) * 2006-10-06 2008-05-15 Nippon Soda Co Ltd 含窒素複素環化合物および有害生物防除剤
JP2008133273A (ja) * 2006-11-01 2008-06-12 Nippon Soda Co Ltd 含窒素へテロ環化合物および有害生物防除剤
WO2009022746A1 (fr) * 2007-08-10 2009-02-19 Nippon Soda Co., Ltd. Composé hétérocyclique contenant de l'azote et agent de lutte contre les animaux nuisibles
WO2009024541A2 (fr) * 2007-08-17 2009-02-26 Intervet International B.V. Compostions d'isoxazoline et leur utilisation en tant qu'antiparasitaires
JP2009062354A (ja) * 2007-08-10 2009-03-26 Nippon Soda Co Ltd 含窒素複素環化合物および有害生物防除剤
JP2010116389A (ja) * 2008-10-17 2010-05-27 Bayer Cropscience Ag 殺虫性アリールピロリジン類
JP2011136928A (ja) * 2009-12-28 2011-07-14 Bayer Cropscience Ag 殺虫性アリールピロリジン類
JP2011178673A (ja) * 2010-02-26 2011-09-15 Nissan Chem Ind Ltd 非農園芸害虫の防除方法

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005085216A1 (fr) * 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. Composé benzamide substitué par de l’isoxazoline et agent de contrôle d’organisme nocif
JP2008110971A (ja) * 2006-10-06 2008-05-15 Nippon Soda Co Ltd 含窒素複素環化合物および有害生物防除剤
JP2008133273A (ja) * 2006-11-01 2008-06-12 Nippon Soda Co Ltd 含窒素へテロ環化合物および有害生物防除剤
WO2009022746A1 (fr) * 2007-08-10 2009-02-19 Nippon Soda Co., Ltd. Composé hétérocyclique contenant de l'azote et agent de lutte contre les animaux nuisibles
JP2009062354A (ja) * 2007-08-10 2009-03-26 Nippon Soda Co Ltd 含窒素複素環化合物および有害生物防除剤
WO2009024541A2 (fr) * 2007-08-17 2009-02-26 Intervet International B.V. Compostions d'isoxazoline et leur utilisation en tant qu'antiparasitaires
JP2010116389A (ja) * 2008-10-17 2010-05-27 Bayer Cropscience Ag 殺虫性アリールピロリジン類
JP2011136928A (ja) * 2009-12-28 2011-07-14 Bayer Cropscience Ag 殺虫性アリールピロリジン類
JP2011178673A (ja) * 2010-02-26 2011-09-15 Nissan Chem Ind Ltd 非農園芸害虫の防除方法

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Publication number Priority date Publication date Assignee Title
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US8735362B2 (en) 2009-12-01 2014-05-27 Syngenta Crop Protection, Llc Insecticidal compounds based on isoxazoline derivatives
US10750745B2 (en) 2009-12-01 2020-08-25 Syngenta Crop Protection, Llc Insecticidal compounds based on isoxazoline derivatives
US10206400B2 (en) 2009-12-01 2019-02-19 Syngenta Participations Ag Insecticidal compounds based on isoxazoline derivatives
US9609869B2 (en) 2009-12-01 2017-04-04 Syngenta Crop Protection, Llc Insecticidal compounds based on isoxazoline derivatives
US9456606B2 (en) 2011-12-14 2016-10-04 Syngenta Participations Ag Pesticidal mixtures
JP2015500316A (ja) * 2011-12-14 2015-01-05 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 有害生物防除混合物
WO2013087710A3 (fr) * 2011-12-14 2013-11-07 Syngenta Participations Ag Mélanges pesticides
WO2014039422A1 (fr) * 2012-09-04 2014-03-13 Zoetis Llc Dérivés d'isoxazoline spirocyclique pour le traitement des poux de mer
US9226928B2 (en) 2012-09-07 2016-01-05 Zoetis Services Llc Spirocyclic isoxazoline parasiticidal combinations
CN104602529B (zh) * 2012-09-07 2016-11-02 硕腾服务有限责任公司 螺环异噁唑啉杀寄生虫组合
AU2013312882B2 (en) * 2012-09-07 2015-11-05 Zoetis Services Llc Spirocyclic isoxazoline parasiticidal combinations
KR101792370B1 (ko) 2012-09-07 2017-11-01 조에티스 서비시즈 엘엘씨 스피로환식 아이소옥사졸린 구충제 조합물
CN104602529A (zh) * 2012-09-07 2015-05-06 佐蒂斯有限责任公司 螺环异噁唑啉杀寄生虫组合
WO2014039475A1 (fr) * 2012-09-07 2014-03-13 Zoetis Llc Combinaisons antiparasitaires d'isoxazoline spirocyclique
JP2015003900A (ja) * 2013-05-23 2015-01-08 宮崎みどり製薬株式会社 ワクモ防除剤
US11034669B2 (en) 2018-11-30 2021-06-15 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof
WO2022003610A1 (fr) 2020-07-02 2022-01-06 Pi Industries Ltd. Dérivés de 2-(4,5-dihydroisoxazol-3-yl) isoindoline-5-carboxamide et composés similaires utilisés comme pesticides pour la protection des cultures
WO2023037253A1 (fr) 2021-09-08 2023-03-16 Pi Industries Ltd Composés d'isoxazoline et leur utilisation en tant qu'agents de lutte contre les nuisibles

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