WO2012086462A1 - Composé isoxazoline et agent de lutte contre les parasites - Google Patents

Composé isoxazoline et agent de lutte contre les parasites Download PDF

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WO2012086462A1
WO2012086462A1 PCT/JP2011/078766 JP2011078766W WO2012086462A1 WO 2012086462 A1 WO2012086462 A1 WO 2012086462A1 JP 2011078766 W JP2011078766 W JP 2011078766W WO 2012086462 A1 WO2012086462 A1 WO 2012086462A1
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group
substituted
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isoxazoline compound
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PCT/JP2011/078766
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Japanese (ja)
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久保田　靖
真也 明石
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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
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides

Definitions

  • the present invention relates to crystals of isoxazoline compounds consisting of a single diastereomer, optically active isoxazoline compounds, and pest control agents.
  • This application claims priority based on Japanese Patent Application No. 2010-283357 filed in Japan on December 20, 2010 and Japanese Patent Application No. 2011-024462 filed on February 7, 2011 in Japan. , The contents of which are incorporated herein.
  • Patent Document 1 describes a compound having the same skeleton as the compound of the present invention.
  • the present invention consists of a single diastereomer that can be synthesized industrially advantageously, has a certain effect, can be an active ingredient of a pest control agent that can be used particularly safely, and can be stably formulated. It is an object of the present invention to provide a crystal of an isoxazoline compound, an optically active isoxazoline compound or a salt thereof, and a pest control agent containing these compounds as active ingredients.
  • the inventors of the present invention have conducted an extensive search in order to solve the above problems. And the present inventors paid attention to the isoxazoline compound or its salt known in Patent Document 1 as an active ingredient of a drug for assisting the growth of agricultural crops, and repeated studies. As a result, it was found that the specific optically active isoxazoline compound or salt thereof obtained by optical resolution of the isoxazoline compound or salt thereof described in Patent Document 1 can achieve both efficacy and safety. Moreover, the crystal
  • the present invention includes the following.
  • Formula (I) (In the formula (I), X represents a halogen atom, an unsubstituted or substituted C1-6 alkyl 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.
  • X ′ represents a halogen atom, an unsubstituted or substituted C1-6 alkyl 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 ′ and is an integer from 0 to 6. When m is 2 or more, X ′ may be the same as or different from each other.
  • R 1 represents a C1-6 haloalkyl 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.
  • R 3 is 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.
  • a single diastereomer of the isoxazoline compound represented by the formula (I) is represented by the formula (I-1) (In the formula (I-1), X, n, X ′, m, R 1 , R 2 , R 3 , and p have the same meaning as in the formula (I)).
  • 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.
  • X ′ represents a halogen atom, an unsubstituted or substituted C1-6 alkyl 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 ′ and is an integer from 0 to 6. When m is 2 or more, X ′ may be the same as or different from each other.
  • R 1 represents a C1-6 haloalkyl 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.
  • R 3 is 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.
  • the optically active isoxazoline compound represented by the formula (II) is represented by the formula (II-1) (In formula (II-1), X, n, X ′, m, R 1 , R 2 , R 3 , and p have the same meaning as in formula (II)).
  • a pest control agent comprising the crystal according to [1] or [2] or the optically active isoxazoline compound or salt thereof according to [3] or [4] as an active ingredient.
  • An insecticide containing, as an active ingredient, the crystal according to [1] or [2], or the optically active isoxazoline compound or salt thereof according to [3] or [4].
  • An animal ectoparasite control agent comprising the crystal according to [1] or [2], or the optically active isoxazoline compound according to [3] or [4] or a salt thereof as an active ingredient.
  • Formula (I) (In the formula (I), X represents a halogen atom, an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group. Show. 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.
  • X ′ represents a halogen atom, an unsubstituted or substituted C1-6 alkyl 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 ′ and is an integer from 0 to 6. When m is 2 or more, X ′ may be the same as or different from each other.
  • R 1 represents a C1-6 haloalkyl 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.
  • R 3 is 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.
  • p represents the number of repeating methylene groups in parentheses and is an integer of either 1 or 2.
  • the diastereomer mixture of the isoxazoline compound represented by the above formula) is dissolved in a solvent in which any two or more of an ether solvent, an ester solvent, a halogen solvent, or a hydrocarbon solvent are mixed, and then crystallized.
  • X represents a halogen atom, an unsubstituted or substituted C1-6 alkyl 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.
  • X ′ represents a halogen atom, an unsubstituted or substituted C1-6 alkyl 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 ′ and is an integer from 0 to 6. When m is 2 or more, X ′ may be the same as or different from each other.
  • R 1 represents a C1-6 haloalkyl 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.
  • R 3 is 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.
  • p represents the number of repeating methylene groups in parentheses and is an integer of either 1 or 2.
  • the diastereomer mixture of the isoxazoline compound represented by the above formula) is dissolved in a solvent in which any two or more of an ether solvent, an ester solvent, a halogen solvent, or a hydrocarbon solvent are mixed, and then crystallized.
  • a solvent in which any two or more of an ether solvent, an ester solvent, a halogen solvent, or a hydrocarbon solvent are mixed, and then crystallized.
  • an optically active isoxazoline compound or a salt thereof that can be advantageously synthesized industrially, has a certain effect, and can be an active ingredient of a pest control agent that can be used particularly safely.
  • crystallization of the isoxazoline compound which consists of a single diastereomer which can be stabilized, and its manufacturing method are provided.
  • These isoxazoline compounds or salts thereof are effective as insecticides, acaricides, sanitary pest control agents, animal ectoparasite control agents, and the like.
  • the crystal of the isoxazoline compound consisting of a single diastereomer of the isoxazoline compound represented by the formula has a relatively high melting point and a narrow temperature range at the start and end points of the melting, and exhibits stable properties as a substance. It is characterized by excellent stability during preparation and in preparation. This is because the mixture of diastereomers is often amorphous, has a low melting point, or is poor in reproducibility of crystallization even when obtained as crystals, and contains a lot of impurities. In contrast to being unsuitable for formulation.
  • the term “unsubstituted” means that the group is only a parent 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 alkylthio group such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group; vinylthio group, allylthio C2-6 alkenylthio groups such as groups; C2-6 alkynylthio groups such as ethynylthio groups and propargylthio groups; C6-10 arylthio groups such as phenylthio groups and naphthylthio groups; heteroarylthio groups such as thiazolylthio groups and pyridylthio groups;
  • 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 heterocyclyl groups such as aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group; trimethylsilyl group, triethylsilyl And a tri-C1-6 alkyl-substituted silyl group such as a t-butyldimethylsilyl group;
  • substituted may be those in which any hydrogen atom in the group is further substituted with another “substituent”.
  • X in the formula (I) represents a halogen atom, an unsubstituted or substituted C1-6 alkyl 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.
  • 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
  • acyloxy C1-6 alkyl group C1-6 alkyl group substituted by imino group such as iminomethyl group, (1-imino) ethyl group, (1-imino) propyl group; hydroxyiminomethyl group, (1-hydroxyimino A C1-6 alkyl group substituted with a hydroxyimino group or an alkoxyimino group such as an ethyl group, a (1-hydroxyimino) -n-propyl group, a methoxyiminomethyl group, a (1-methoxyimino) ethyl group; Benzyl group having one or more substituents, unsubstituted or having substituents C7 ⁇ 11 aralkyl group having unsubstituted or substituted group, such that a phenethyl 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 can be mentioned.
  • 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.
  • X ′ in the formula (I) represents a halogen atom, an unsubstituted or substituted C1-6 alkyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a nitro group, or a cyano group.
  • Show. m represents the number of substitutions of X ′ and is an integer from 0 to 6. When m is 2 or more, X ′ may be the same as or different from each other.
  • R 1 ) R 1 in the formula (I) represents a C1-6 haloalkyl group.
  • R 1 a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a trifluoromethyl group, a trichloromethyl group, a 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, Examples include 2,2-trifluoro-1-trifluoromethylethyl group, perfluorohexyl group, perchlorohexyl group, 2,4,6-trichlorohexyl group, and the like. Of these, R 1 is preferably a trifluoromethyl group.
  • R 2 ) R 2 in formula (I) has a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-7 acyl group, or an unsubstituted or substituted group C1-6 alkoxycarbonyl group.
  • Examples of the “C1-7 acyl group” in R 2 include formyl group, acetyl group, propionyl group, benzoyl group and the like.
  • Examples of the “substituted C1-7 acyl group” in R 2 include halogen-substituted C1-7 acyl groups such as a chloroacetyl group, a trifluoroacetyl group, a trichloroacetyl group, and a 4-chlorobenzoyl group.
  • C1 ⁇ 6 alkoxycarbonyl group in R 2 is a methoxycarbonyl group, an ethoxycarbonyl group, n- propoxycarbonyl group, and the like i- propoxycarbonyl group.
  • Examples of the “substituted C1-6 alkoxycarbonyl group” in 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
  • R 3 in formula (I) is 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, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C2-6 alkenyloxy group, A substituted or substituted C2-6 alkynyloxy group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heterocyclic group is shown.
  • Examples of the “C1-6 alkyl group” and the “C1-6 alkoxy group” in R 3 include the same groups as those described above for X.
  • C2-6 alkenyl group 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” for R 3 include C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group;
  • Examples of the “C2-6 alkynyl group” in R 3 include 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 And a 1,1-dimethyl-2-butynyl group.
  • Examples of the “substituted C2-6 alkynyl group” in R 3 include C2-6 such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group and the like. Haloalkynyl group; and the like.
  • Examples of the “C3-8 cycloalkyl group” in R 3 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • Examples of the “cycloalkyl group having a substituent” 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, 1-propenyloxy group, 2-propenyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 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, And 2-hexenyloxy group.
  • Examples of the “substituted C2-6 alkenyloxy group” for R 3 include C2-6 haloalkenyloxy groups such as 2-chloro-1-propenyloxy group and 2-fluoro-1-butenyloxy group; Can do.
  • 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- A hexynyloxy group can be exemplified.
  • 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.
  • a C2-6 haloalkynyloxy group such as;
  • the “C6-10 aryl group” for R 3 may be monocyclic or polycyclic. In the polycyclic aryl group, if 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; be able to.
  • 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 C 1-6 alkyl group, a C 1-6 alkoxy C 1-6 alkyl group, or a C 1-6 alkoxy C 1-6 alkoxy C 1-6 alkyl group.
  • (P) p represents the number of repeating methylene groups in parentheses and is an integer of either 1 or 2. p is preferably 1. The part of the ring containing p is a cyclopentane ring when p is 1 and a cyclohexane ring when p is 2. In the formula (I), it preferably has an indane ring.
  • the carbon attached with * on the isoxazoline and the carbon attached with ** on the saturated ring in the following formula (1) are asymmetric carbons.
  • X, n, X ′, m, R 1 , R 2 , R 3 , and p have the same meaning as in formula (I).
  • the isoxazoline compound represented by the formula (I) has at least four stereoisomers.
  • a single diastereomer is a crystal having a relatively high melting point and a narrow temperature range at the start and end points of the melting.
  • a single diastereomer particularly includes an isoxazoline compound represented by the following formula (I-1) (hereinafter sometimes referred to as (S, S) form), and a formula (I It is preferably a combination of stereoisomers of the isoxazoline compound represented by -2) (hereinafter sometimes referred to as (R, R) form).
  • (I-1) hereinafter sometimes referred to as (S, S) form
  • (I It is preferably a combination of stereoisomers of the isoxazoline compound represented by -2) (hereinafter sometimes referred to as (R, R) form).
  • the isoxazoline compound represented by the formula (I) As the isoxazoline compound represented by the formula (I), the isoxazoline compound described in WO2009 / 022746 is applicable. A mixture of diastereomers of the isoxazoline compound represented by the formula (I) can be produced by a production method described in WO2009 / 022746. Then, the obtained mixture of diastereomers of the isoxazoline compound is dissolved in a solvent obtained by mixing any two or more of an ether solvent, an ester solvent, a halogen solvent, or a hydrocarbon solvent, and then crystallized. Crystallization of an isoxazoline compound consisting of a single diastereomer can be produced by analyzing.
  • ether solvents that can be used for the production include diethyl ether, tetrahydrofuran, 1,4-dioxane, methyl t-butyl ether, dimethoxyethane, and the like.
  • ester solvent include ethyl acetate, n-propyl acetate, and t-butyl acetate.
  • halogen solvent include methylene chloride, chloroform, 1,1,1-trichloroethane and the like.
  • hydrocarbon solvent include hexane, heptane, cyclohexane, benzene, toluene and the like.
  • a mixed solvent of an ester solvent and a hydrocarbon solvent is preferable.
  • isooxazoline compound represented by the formula (I) include the following compounds.
  • a combination of the (S, S) isomer and the corresponding (R, R) isomer constitutes a crystal of the isoxazoline compound comprising the single diastereomer of the present invention.
  • the combination of the (S, S) body and the corresponding (R, R) body forms a crystal having a relatively high melting point and a narrow temperature range at the melting start point and end point, and the (S, S) body is included. Since it has the highest activity among the four stereoisomers, this crystal is effective as the main component of the pest control agent.
  • optically active isoxazoline compound The optically active isoxazoline compound of the present invention is a compound represented by the formula (II).
  • X, n, X ′, m, R 1 , R 2 , R 3 , and p have the same meanings as in the formula (I).
  • (*, **) * And ** indicate that the attached carbon atom is optically active, meaning that the abundance of a specific isomer for that carbon atom is greater than 50%.
  • the abundance of the one particular isomer is 90% or more, more preferably 95% or more, and even more preferably 98% or more.
  • optically active isoxazoline compound in addition to the (S, S) isomer and (R, R) isomer described above, (S, R) isomer and (R, S) isomer which are diastereomers different from these are used. Can be mentioned.
  • optically active isoxazoline compound represented by the formula (II) the optically active form of the isoxazoline compound described in WO2009 / 022746 is applicable.
  • the optically active isoxazoline compound represented by the formula (II) can be obtained by obtaining an isoxazoline compound by a production method described in WO2009 / 022746 and dividing it by a known optical resolution method. Further, it can be obtained by synthesis by a known asymmetric synthesis method.
  • optically active isoxazoline compound examples include the following compounds. N-((R) -5-((S) -5- (3,5-dichloro-phenyl) -5- (trifluoromethyl) -4,5- (dihydroisoxazol-3-yl) -2 , 3-Dihydro-1H-inden-1-yl) propanamide [English: N-((R) -5-((S) -5- (3,5-Dichloro-phenyl) -5- (trifluoromethyl)- 4,5-dihydroisoxazol-3-yl) -2,3-dihydro-1H-inden-1-yl) propanamide], N-((R) -5-((R) -5- (3,5-dichloro) -Phenyl) -5- (trifluoromethyl) -4,5- (dihydroisoxazol-3-yl) -2,3-dihydro-1H-in-y
  • the salt of the compound represented by the formula (II) includes inorganic acid salts such as hydrochloride, nitrate, sulfate and phosphate; organic salts such as acetate, lactate, propionate and benzoate.
  • inorganic acid salts such as hydrochloride, nitrate, sulfate and phosphate
  • organic salts such as acetate, lactate, propionate and benzoate.
  • the pest control agent of the present invention contains the optically active isoxazoline compound of the present invention or a salt thereof as an active ingredient.
  • Control targets include pests such as pests and ticks on crops, fruit trees, flower buds, or trees. That is, the pest control agent of the present invention is effective as an insecticide and acaricide that protects the above-mentioned crops and the like. Examples of target pests and mites are shown below.
  • Lepidoptera pests such as Spodoptera litura, Mamestra brassicae, Agrotis ypsilon, Autographa nigrisigna, Plutella xylostella, Adeno hon, mai, hon Homona magnanima), peach sigai (Carposina sasakii), pear tiger squirrel (Grapholitha molesta), mandarin moth (Phyllocnistis citrella), chanohosoga (Caloptilia theivora), kinmonhosoga (Phyllonorycter ringoniella), maiparigai (Lymanttis quaga) suppressalis, Cnaphalocrocis medinalis, European corn borer (Ostrinia nubilalis), Hyphantria cunea, Cadra cautella, Heliothis spp., Heliothis spp.
  • Hemiptera pests for example, Myzus persicae, cotton aphids (Aphis gossypii), black-headed aphids (Lipaphis erysimi), barley beetles (Rhopalosiphum padi), Rasptortus clava Crocodile bug (Acrosternum hilare), billworm (Unaspis yanonensis), stag beetle (Pseudococcus comstocki), whitefly (Trialeurodes vaporariorum), tobacco whitefly (Bemisia tabaci), genti olila Nashigumbai (Stephanitis nashi), brown planthopper (Nilaparvata ⁇ lugens), brown planthopper (Laodelphax ⁇ stratella), white-tailed planthopper (Sogatella furcifera), leafhopper leafhopper (Nephotettix cincticeps), etc .;
  • Coleoptera pests for example, Phyllotreta striolata, Aulacophora indica, Colorado potato beetle (Leptinotarsa decemlineata), rice weevil (Lissorhoptrus oryzophilus), Sweeophilus osooryza (Sitophilus osooryza) japonica, Anomala rufocuprea, Diabrotica spp., Tobacco beetle (Lasioderma serricorne), Lyctus brunneus, Monochamus alternatca (Monochamus alternatca), Monochamus alternatca Agriotes spp.), Epilachna vigintioctomaculata, Tenebroides mauritanicus, cotton weevil (Anthonomus grandis), etc .;
  • Diptera pests for example, Bactrocera cucurbitae, Bactrocera dorsalis, Delia platura, Hydrellia griseola, Drosophila melanogaster, etc .; (5) Thripidae pests, for example, Thrips palmi, Scirtothrips dorsalis, etc .; (6) Hymenoptera pests, for example, Monomorium pharaonis, Vespa simillima, Athalia rosae, etc .; (7) Diptera pests, such as Locusta migratoria;
  • Cockroach (Blattodea) pests such as German cockroach (Blattella germanica), Black cockroach (Periplaneta fuligginosa), Japanese cockroach (Periplaneta japonica), American cockroach (Periplaneta americana), Black cockroach (Periplaneta australasiae); (9) Termite pests such as termites (Coptotermes formosanus), termites (Reticulitermes speratus), (10) Plant parasitic nematodes, for example, sweet potato nematode (Meloidogyne incognita), Negusale nematodes, soybean cyst nematode (Heterodera glycines), rice scented nematode (Aphelenchoides besseyi), pine wood nematode (Bursaphelenchus xylophil;
  • Astigmata (A) Acaridae mites, for example, Rhizoglyphus echinopus, Rhizoglyphus robini; Rhizoglyphus robini; Tyrophagus spp., Tyrophagus spp. Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus similis; Others, Acarus siro, Mysticus (Aleuroglyphus cetus)
  • Prostigmata mite (Actinedida) (A) mites of the Tetranychidae family, for example of the genus Bryobia spp., Clover spider mite (Bryobia praetiosa), fake clover spider mite (Bryobia rubrioculus); Aid spider mite (Eotetranychus sidani) (Eotetranychus seidu) (Eotetranychus shii) ), White spider mite (Eotetranychus asiaticus), Eotetranychus kankitus; eg Oligonychus mangiferus, Oligonychus perseae, ulosus Spider mite (Oligonychus karamatus), Sugino spider mite (Oligonychus hondoensis), Crimson spider mite (Oligonychus ununguis), Rice spider mite (Oligonychus shinkajii), sugarcane spider mite
  • the green spider mite (Sasanychus spp.), The green spider mite (Sasanychus akitanus), the Japanese spider mite (Sasanychus pusillus); ), Spider spider mite (Shizotetranychus longus), Spider spider mite (Shizotetranychus schizopus), Shizotetranychus recki;
  • Tenuipalpidae ticks for example, Brevipalpus spp., Brevipalpus lewsulus, Brevipalpus russulus, Brevipalpus obovatus, Penis phoeni );
  • Tenuipalpus spp. Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; and others, Dolichotetranychus floridanus;
  • C Eriophyidae mites such as Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Carnation mite (Aceria paradianthi), black spider mite (Aceria tiyingi), tulip spider mite (Aceria tulipae), Shibahamaki fushi mite (Aceria zoysiea); for example, Eriophyes spp., Eriophyes chibaensis, For example,
  • the pest control agent of the present invention can be further used to control pests such as sanitary pests, storage shell pests, clothing pests, house pests, and parasites.
  • pests such as sanitary pests, storage shell pests, clothing pests, house pests, and parasites.
  • the ectoparasites that are subject to control include those that inhabit the back, underarms, lower abdomen, and inner crotch of the host animal and obtain nutrients such as blood and dandruff from the animal, and the back of the host animal. Including those that fly to the buttocks, etc., and inhabit by obtaining nutrients such as blood and dandruff from animals.
  • ectoparasites include ticks, lice and fleas.
  • Examples of host animals in which the 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 bees); That is, the pest control agent of the present invention is effective as an ectoparasite control agent for animals that protects the above animals.
  • Acari The following pests are listed as target mites (Acari).
  • mite (A) Dermanyssidae mites, for example, Dermanyssus gallinae from the genus Dermanyssus spp .; (B) mites of the family Mronyssidae, for example, Ornithonyssus spp., Ornithonyssus sylviarum, Ornithonyssus bursa, Ornithonyssus bacoti; (C) Mites from the family Laelapidae, such as Laelaps echidninus, Laelaps jettmari; Tropilaelaps clarae (D) Varroidae mites, for example, Varroa spp., Varroa destructor, Varroa jacobsoni, Varroa underwoodi;
  • 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;
  • Ischnocera subs (biting louse)
  • Philopteridae lice for example, Columbicola spp., Columbicola columbae; for example, Cuclotogaster spp., Cuclotogaster spp. heterographus
  • Goniodes spp. Goniodes dissimilis
  • Goniodes gigas Goniodes gallinae
  • Lipeurus spp eg, Lipeurus spp.
  • Trichodectidae such as Bovicola spp., Bovicola bovis, Bovicola ovis, Bovicola limbata, Bovicola e, Bovicola capra Bovicola equi; for example, Trichodectes spis., Trichodectes canis; for example, Felicola spp., Felicola subrostrata;
  • 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, Leptopsyllidae, for
  • target ectoparasites include bugs of the order of stink bugs.
  • insects of the order of the Hemiptera insects of the order of the Hemiptera.
  • 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
  • Triatoma infestans from the genus Triatoma spp .
  • A 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
  • Triatoma infestans from the genus Triatoma spp .
  • Triatoma infestans from the genus Triatom
  • insects of the order Diptera which are biting insects (chewable flies, blood-sucking adult flies, migratory dipterous larvae, parasitic flies).
  • Nematocera 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
  • 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);
  • the pest control agent of the present invention may be used in combination with or in combination with other active ingredients such as fungicides, other insecticides / miticides, nematicides, soil insecticides, plant regulators and the like. Typical examples of fungicides, other insecticides / acaricides, nematicides, soil insecticides, and plant growth regulators that can be used in combination with the pest control agent of the present invention are shown below.
  • Insecticides, acaricides, nematicides, soil insecticides (1) 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, dis
  • 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) Organochlorine; camfechlor, chlordane, endosulfan, HCH, ⁇ -HCH, heptachlor, methoxychlor (7) macrocyclic lactone insecticide: abamectin, emamectin benzoate, milbemectin, lepimectin, spinosad, ivermectin, selamectin, doramectin, Epinomectin, moxidectin, (8) ME
  • Oxidative phosphorylation inhibitor compounds cyhexatin, diafenthiuron, phenbutatin oxide, propargite, azocyclotin; (12) molting disruptor: cyromazine; (13) Mixed function oxidase inhibitor compound: piperonyl butoxide; (14) Sodium channel blocker compounds: indoxacarb, metaflumizone; (15) Microbial pesticides: BT agent, entomopathogenic virus agent, entomopathogenic fungus agent, nematode pathogenic fungus agent; Bacillus spp.
  • Latrophilin receptor agonist depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;
  • Octopaminergic agent Amitraz;
  • Ryanodine derivative agonist fulvendiamide, chlorantraniliprole, cyantraliniprol
  • Inhibitor of magnesium-stimulated ATPase thiocyclam, thiosultap, nereistoxin;
  • Antifeedant Pymetrozine; (21) Tick growth inhibitor: clofentezin, etoxazole;
  • Others Benclothiaz, Bifenazate, Pyridalyl, Sulfur, Sienopyraphene, Ciflumethofene, Amidoflumet, Tetradiphone, Chlordimeform, 1,3-Dichloropropene, DCIP, Phenisobromolate, Benzomate, Metaalde
  • Fungicide (1) benzimidazole series: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate methyl, etc .; (2) Dicarboximide type: Clozolinate, iprodione, procymidone, vinclozolin and the like; (3) DMI-bactericidal system: imazalyl, oxpoconazole, pefazoate, prochloraz, triflumizole, triphorin, pyrifenox, fenarimol, nuarimol, azaconazole, viteltanol, bromconazole, cyproconazole, difenoconazole, diniconazole, Epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafor, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propicon
  • Phenylamide Benalaxyl, furaxyl, metalaxyl, metalaxyl-M, oxadixyl, ophthalse, etc .; (5) Amine type: aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine and the like; (6) phosphorothiolate type: EDDP, iprobenphos, pyrazophos, etc .; (7) Dithiolane type: isoprothiolane and the like; (8) Carboxamide: benodanyl, boscalid, carboxin, fenfuran, flutolanyl, furamethopyl, mepronil, oxycarboxin, pentiopyrad, tifluzamide and the like; (9) Hydroxy- (2-amino) pyrimidine series: bupyrimeto, dimethylolymol, ethylimole
  • AP fungicide anilinopyrimidine type: cyprodinil, mepanipyrim, pyrimethanil, etc .
  • QoI-bactericidal (Qo inhibitor) system azoxystrobin, picoxystrobin, pyraclostrobin, cresoxime-methyl, trifloxystrobin, dimoxystrobin, metminostrobin, orizastrobin, Famoxadone, floxastrobin, phenamidon, metminophen, etc .
  • PP fungicide phenylpyrrole
  • Quinoline series quinoxyphene, etc .;
  • AH fungicide (aromatic hydrocarbon) series biphenyl, chloronebu, dichlorane, kintozen, technazen, tortofos-methyl, etc .
  • MBI-R series fusaride, pyrokilone, tricyclazole, etc .
  • MBI-D system carpropamide, diclocimet, phenoxanyl, etc .
  • SBI agents fenhexamide, pyributicarb, terbinafine, etc .
  • Phenylurea Pencyclon, etc .
  • QiI-bactericides (Qi inhibitors) cyazofamide, etc .
  • (21) Benzamide series Zoxamide and the like
  • (22) Enopyranuron series blastcidin, mildiomycin, etc .
  • Hexopyranosyl Kasugamycin, etc.
  • Phosphate ester phosphorous acid, tolcrofosmethyl, fosetyl and the like;
  • Phthalamic acid type Teclophthalam, etc .;
  • Benzotriazine series triazoxide and the like;
  • Benzenesulfonamide series fullsulfamide and the like;
  • Pyridazinone Dichromedin and the like;
  • Tetracycline oxytetracycline, etc .;
  • Thiocarbamate type metasulfocarb, etc.
  • Plant growth regulator Abscisic acid, indole butyric acid, uniconazole, etiquelozate, etephone, cloxiphonac, chlormecote, chlorella extract, calcium peroxide, cyanamide, dichlorprop, gibberellin, daminozide, decyl alcohol, trinexapac ethyl, mepicoat chloride, pack Lobutrazole, paraffin wax, piperonyl butoxide, pyraflufenethyl, flurprimidol, prohydrojasmon, prohexadione calcium salt, benzylaminopurine, pendimethalin, forchlorphenuron, potassium maleate hydrazide, 1-naphthyl Acetamide, 4-CPA, MCPB, choline, oxyquinoline sulfate, ethiclozeate, butorualine, 1-methylcyclopropene, abiglycine hydrochloride;
  • the pest control agent of the present invention may contain only an active ingredient, but may contain a carrier such as a solid carrier, a liquid carrier or a gaseous carrier. Moreover, the pest 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. Furthermore, a surfactant and other auxiliary agents may be added as necessary.
  • the pest control agent of the present invention is in a form that can be taken by general agricultural chemicals, that is, wettable powder, granule, powder, emulsion, aqueous solvent, suspension, granular wettable powder, flowable, microcapsule, aerosol, fumes.
  • general agricultural chemicals that is, wettable powder, granule, powder, emulsion, aqueous solvent, suspension, granular wettable powder, flowable, microcapsule, aerosol, fumes.
  • an agent a heat transpiration agent, a smoke agent, and an acaricide
  • it can be formulated into a form such as a bait agent.
  • Additives and carriers used in formulation into solid dosage forms include vegetable powders such as soybean flour and wheat flour, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite and clay And organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate.
  • Solvents used in formulating liquid dosage forms include kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil , Vegetable oil, water and the like.
  • gaseous carriers used when formulating into a propellant include butane gas, LPG, dimethyl ether, carbon dioxide gas, and the like.
  • food ingredients such as cereal flour, vegetable oil, sugar and crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, 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 as necessary.
  • the surfactant that can be added is not particularly limited.
  • alkyl phenyl ether added with polyoxyethylene alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, sorbitan higher fatty acid ester added with polyoxyethylene, tristyryl added with polyoxyethylene
  • Nonionic surfactants such as phenyl ether, sulfates of alkylphenyl ethers added with polyoxyethylene, alkylbenzene sulfonates, sulfates of higher alcohols, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfones Acid salt, formaldehyde condensate of alkyl naphthalene sulfonate, and isobutylene-maleic anhydride copolymer.
  • the content of the active ingredient in the preparation is usually preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, based on the whole preparation.
  • the wettable powder, emulsion, flowable powder, aqueous solvent, and granular wettable powder thus obtained are diluted with water to a predetermined concentration to obtain a solution, suspension or emulsion.
  • Granules can be sprayed on plants or soil as they are.
  • preparations supplied in the form of oils, aerosols, fumes, poison baits, mite-proof sheets, etc. can be used as they are.
  • the pest control agent of the present invention when used as an acaricide for controlling mites parasitic on livestock such as cattle and pigs, and pet animals such as dogs and cats,
  • the active ingredient can be used in an amount of 0.01 to 1000 mg.
  • the acaricide for control can be applied by a known veterinary technique.
  • animals such as tablets, capsules, soaking solutions, feed mixing, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.)
  • administration by spraying, pour-on, dropping (spot-on), etc. with oily or aqueous solutions
  • optical resolution was performed by a known method using chiral HPLC.
  • the analytical test results of the obtained optically active isoxazoline compounds (optically active compounds A to D) and the [ ⁇ ] D value of each optically active compound are shown below.
  • Flow rate 1.0 mL / min.
  • Step 1 Synthesis of (R) -5-bromo-indan-1-ol (hereinafter sometimes referred to as compound [(R) -2]) 200 ml glass neck set with three-way cock and bubbler Into the flask was placed a fluororesin-coated stir bar, 40 g (190 mmol) of 5-bromo-indan-1-one, 47 ml of N, N-dimethylformamide and 94 ml of formic acid-triethylamine (5: 2 azeotrope). Ultrasonic deaeration was performed while replacing.
  • the analytical conditions for chiral HPLC are as follows.
  • the measurement temperature was 20 ° C.
  • DAICEL CHIRALPACK AD-3 25 cm ⁇ ⁇ 4.6 mm
  • a 1 ml / min UV (220 nm) detector was used.
  • the retention time of S-form was 8.0 minutes
  • the retention time of R-form was 9.9 minutes.
  • Step 2 Synthesis of (S) -5-bromo-indan-1-ylamine (hereinafter sometimes referred to as compound [(S) -3])
  • Compound [(R ) -2] (8.52 g, 40 mmol) in 30 ml of toluene solution at a temperature range of ⁇ 5 to 0 ° C., 30 ml of (PhO) 2 P (O) N 3 (13.2 g, 48 mmol) in toluene solution and 30 ml of a toluene solution of diazabicycloundecene (7.31 g, 48 mmol) was added and stirred for 1 hour in the same temperature range. Then it was warmed to room temperature.
  • Kiriyama funnel was filled with celite and diamine silica for heavy metal removal, and the organic layer was poured into it and suction filtered. The solvent was distilled off to obtain a crude azide product.
  • the Kiriyama funnel was filled with silica gel, and the azide crude product was put therein and eluted with a 97/3 mixed solution of n-hexane / ethyl acetate. The eluate was distilled off.
  • Step 3 Synthesis of (S) -N- (5-bromo-indan-1-yl) -3-methoxy-propionamide (hereinafter sometimes referred to as compound [(S) -4]).
  • Step 4 Synthesis of (S) -N-5-acetyl-indan-1-yl) -3-methoxy-propionamide (hereinafter sometimes referred to as compound [(S) -5])
  • compound [(S) -5] Three-way cock and argon
  • a fluororesin-coated stirrer 6.68 g (22.4 mmol) of the above compound [(S) -4], 5.6 g (553.9 mmol) of n-butyl vinyl ether, Potassium carbonate (3.72 g, 26.9 mmol), N, N-dimethylformamide (75 ml) and water (19 ml) were added, and the inside of the flask was ultrasonically deaerated while replacing with argon.
  • Step 6 3-methoxy-N- (5- (5- (trifluoromethyl) -5- (3- (trifluoromethyl) phenyl) -4,5-dihydroisoxazol-3-yl) -2 , 3-Dihydro-1H-inden-1-yl) propanamide (hereinafter sometimes referred to as compound [(S) -7]) 48.5 mg (0 0.1 mmol), 20 mg (0.3 mmol) of 50% aqueous hydroxylamine solution and 2 mL of a chloroform solution of N-3,5-trifluoromethylbenzylquinidinium bromide (6.3 mg, 10 mol%) were cooled to 0 ° C. and stirred.
  • compound [(S) -7] 3-methoxy-N- (5- (5- (trifluoromethyl) -5- (3- (trifluoromethyl) phenyl) -4,5-dihydroisoxazol-3-yl) -2 , 3-Dihydro-1H
  • optically active compounds can be produced by a method similar to the above method.
  • the precipitated crystals were filtered, and the obtained crystals were further recrystallized with a mixed solvent of ethyl acetate-hexane to obtain crystals consisting of a single diastereomer (1.85 g, 37%).
  • the melting point of the obtained crystal was 129 to 130 ° C.
  • the precipitated crystals were filtered, and the obtained crystals were further recrystallized with a mixed solvent of ethyl acetate-hexane to obtain crystals consisting of a single diastereomer (70 mg, 33%).
  • the melting point of the obtained crystal was 208-209 ° C.
  • formulation examples of the pest control agent of the present invention are shown, the additives and addition ratios should not be limited to these examples, and can be varied in a wide range.
  • the part in a formulation example shows a weight part. Examples of preparations for agriculture and horticulture are shown below.
  • Formulation Example 1 (wettable powder) Active ingredient 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate 4 parts Alkyl naphthalene sulfonate 3 parts The above ingredients were mixed uniformly and finely pulverized to obtain a wettable powder with 40% active ingredient.
  • Formulation Example 2 Active ingredient 30 parts Xylene 33 parts Dimethylformamide 30 parts Polyoxyethylene alkyl allyl ether 7 parts The above components were mixed and dissolved to obtain an emulsion containing 30% active ingredient.
  • Formulation Example 3 Active ingredient 5 parts Kaolin 94 parts White carbon 1 part An active ingredient 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 Example 4 Active ingredient 0.1-1 part peanut oil After balance preparation, filter sterilize with a sterilization filter.
  • Test examples of the pest control agent of the present invention obtained as described above are shown below.
  • Test Example 1 Efficacy Confirmation Test for Ayayoto An emulsion was obtained according to the formulation shown in Formulation Example 2. It was diluted with water so that the optically active compound concentration was 0.49 ppm. Corn leaves were immersed in the diluted solution for 30 seconds. Corn leaves were air-dried and then placed in plastic containers with filter paper. It was inoculated with 5 second-instar larvae. The plastic container was covered and placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 65%. After 6 days, the life-and-death of Ayayotou was examined, and the insecticidal rate was determined. The test was performed in duplicate. As a result, an insecticidal rate of 100% was shown in corn leaves in which an emulsion using the optically active compound B ((S, S) form) was immersed.
  • optically active compound B ((S, S) form
  • FIG. 1 shows an HPLC chart of a mixture of diastereomers.
  • FIG. 2 shows an HPLC chart of the crystals obtained after crystallization.
  • FIG. 3 shows an HPLC chart of a mixture of diastereomers.
  • FIG. 4 shows an HPLC chart of crystals obtained after crystallization.
  • Example of (3) FIG. 5 shows an HPLC chart of a mixture of diastereomers.
  • FIG. 6 shows an HPLC chart of crystals obtained after crystallization.
  • an optically active isoxazoline compound or a salt thereof that can be synthesized industrially advantageously, has a certain effect, and can be an active ingredient of a pest control agent that can be used safely.
  • crystallization of the isoxazoline compound which consists of a single diastereomer which can be stabilized, and its manufacturing method are provided.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Public Health (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne: un composé ayant un excellent effet de lutte contre les organismes parasitaires externes tels que les tiques et les puces ; des cristaux d'un composé isoxazoline représenté par la formule (I), lesdits cristaux étant composés d'un diastéréomère individuel du composé isoxazoline ; et un agent de lutte contre les organismes parasitaires externes pour des animaux, ledit agent de lutte contre les organismes parasitaires externes comprenant le composé précédemment mentionné en tant qu'ingrédient actif. Selon la présente invention, une préparation stable du composé précédemment mentionné peut être obtenue par cristallisation de celui-ci en tant que diastéréomère individuel. [Dans la formule (I) : X représente un atome d'halogène, etc. ; n, qui représente le nombre de substituant(s) X(s), est un entier de 0-5 ; X' représente un atome d'halogène ; m, qui représente le nombre de substituant(s) X'(s), est un entier de 0-6 ; R1 représente un groupe haloalkyle en C1-6 ; R2 représente un atome d'hydrogène, etc. ; R3 représente un atome d'hydrogène, un groupe alkyle en C1-6 substitué ou non substitué, etc. ; et p, qui représente le nombre de répétitions de groupe(s) méthylène dans les parenthèses, est en entier de 1 ou 2].
PCT/JP2011/078766 2010-12-20 2011-12-13 Composé isoxazoline et agent de lutte contre les parasites WO2012086462A1 (fr)

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013119442A1 (fr) 2012-02-06 2013-08-15 Merial Limited Compositions vétérinaires orales parasiticides comprenant des agents actifs à action systémique, procédés et utilisation associés
WO2013126694A1 (fr) 2012-02-23 2013-08-29 Merial Limited Composition topique comprenant du fipronil et de la perméthrine et ses méthodes d'utilisation
WO2013087710A3 (fr) * 2011-12-14 2013-11-07 Syngenta Participations Ag Mélanges pesticides
WO2014019957A3 (fr) * 2012-08-03 2014-04-17 Syngenta Participations Ag Procédés de lutte antiparasitaire dans du soja
GB2509361A (en) * 2012-11-01 2014-07-02 Sumitomo Chemical Co Isoxazoline compound for use in controlling an animal ectoparasite
WO2015066277A1 (fr) 2013-11-01 2015-05-07 Merial Limited Composés d'isoxazoline antiparasitaires et pesticides
JP2015526522A (ja) * 2012-08-31 2015-09-10 ゾエティス・エルエルシー １−（５’−（５−（３，５−ジクロロ−４−フルオロフェニル）−５−（トリフルオロメチル）−４，５−ジヒドロイソオキサゾール−３−イル）−３’ｈ−スピロ［アゼチジン−３，１’−イソベンゾフラン］−１−イル）−２−（メチルスルホニル）エタノンの結晶形態
WO2015161224A1 (fr) 2014-04-17 2015-10-22 Merial, Inc. Utilisation de composés de malononitrile pour protéger des animaux contre les parasites
WO2016138339A1 (fr) 2015-02-26 2016-09-01 Merial, Inc. Formulations injectables à action prolongée comprenant un agent actif à base d'isoxazoline, méthodes et utilisations de celles-ci
WO2016187534A1 (fr) 2015-05-20 2016-11-24 Merial, Inc. Composés depsipeptidiques anthelminthiques
WO2018071535A1 (fr) 2016-10-14 2018-04-19 Merial, Inc. Composés de vinyl-isoxazoline pesticides et parasiticides
WO2018093920A1 (fr) 2016-11-16 2018-05-24 Merial, Inc. Composés depsipeptidiques anthelminthiques
WO2019036407A1 (fr) 2017-08-14 2019-02-21 Merial, Inc. Composés de pyrazole-isoxazoline à activité pesticide et parasiticide
WO2020014068A1 (fr) 2018-07-09 2020-01-16 Boehringer Ingelheim Animal Health USA Inc. Composés hétérocycliques anthelminthiques
WO2020112374A1 (fr) 2018-11-20 2020-06-04 Boehringer Ingelheim Animal Health USA Inc. Composé indazolylcyanoéthylamino, compositions associées, procédé de fabrication et procédés d'utilisation de celui-ci
WO2020191091A1 (fr) 2019-03-19 2020-09-24 Boehringer Ingelheim Animal Health USA Inc. Composés d'aza-benzothiophène et d'aza-benzofurane anthelminthiques
WO2021242581A1 (fr) 2020-05-29 2021-12-02 Boehringer Ingelheim Animal Health USA Inc. Composés hétérocycliques anthelminthiques
WO2022162016A1 (fr) 2021-01-27 2022-08-04 Intervet International B.V. Composés de cyclopropylamide contre des parasites chez les poissons
WO2022162001A1 (fr) 2021-01-27 2022-08-04 Intervet International B.V. Composés de cyclopropylamide contre des parasites chez les poissons
WO2023156938A1 (fr) 2022-02-17 2023-08-24 Boehringer Ingelheim Vetmedica Gmbh Procédé et système pour fournir un dispositif d'expédition de produit fluide

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
JP2009286773A (ja) * 2008-03-14 2009-12-10 Bayer Cropscience Ag 殺虫性縮環式アリール類
WO2010027051A1 (fr) * 2008-09-04 2010-03-11 日産化学工業株式会社 Composé acétophénone substitué, son procédé de production, et son utilisation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
JP2009286773A (ja) * 2008-03-14 2009-12-10 Bayer Cropscience Ag 殺虫性縮環式アリール類
WO2010027051A1 (fr) * 2008-09-04 2010-03-11 日産化学工業株式会社 Composé acétophénone substitué, son procédé de production, et son utilisation

Cited By (26)

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Publication number Priority date Publication date Assignee Title
WO2013087710A3 (fr) * 2011-12-14 2013-11-07 Syngenta Participations Ag Mélanges pesticides
US9456606B2 (en) 2011-12-14 2016-10-04 Syngenta Participations Ag Pesticidal mixtures
WO2013119442A1 (fr) 2012-02-06 2013-08-15 Merial Limited Compositions vétérinaires orales parasiticides comprenant des agents actifs à action systémique, procédés et utilisation associés
EP3061454A1 (fr) 2012-02-06 2016-08-31 Merial, Inc. Compositions vétérinaires orales parasiticides comprenant des agents actifs à action systémique, procédés et utilisations de celles-ci
EP3766491A1 (fr) 2012-02-06 2021-01-20 Boehringer Ingelheim Animal Health USA Inc. Compositions vétérinaires orales parasiticides comprenant des agents actifs à action systémique, procédés et leurs utilisations
EP3659439A1 (fr) 2012-02-23 2020-06-03 Boehringer Ingelheim Animal Health USA Inc. Composition topique comprenant du fipronil et de la perméthrine et ses procédés d'utilisation
WO2013126694A1 (fr) 2012-02-23 2013-08-29 Merial Limited Composition topique comprenant du fipronil et de la perméthrine et ses méthodes d'utilisation
WO2014019957A3 (fr) * 2012-08-03 2014-04-17 Syngenta Participations Ag Procédés de lutte antiparasitaire dans du soja
JP2015526522A (ja) * 2012-08-31 2015-09-10 ゾエティス・エルエルシー １−（５’−（５−（３，５−ジクロロ−４−フルオロフェニル）−５−（トリフルオロメチル）−４，５−ジヒドロイソオキサゾール−３−イル）−３’ｈ−スピロ［アゼチジン−３，１’−イソベンゾフラン］−１−イル）−２−（メチルスルホニル）エタノンの結晶形態
GB2509361A (en) * 2012-11-01 2014-07-02 Sumitomo Chemical Co Isoxazoline compound for use in controlling an animal ectoparasite
WO2015066277A1 (fr) 2013-11-01 2015-05-07 Merial Limited Composés d'isoxazoline antiparasitaires et pesticides
EP3733664A1 (fr) 2013-11-01 2020-11-04 Boehringer Ingelheim Animal Health USA Inc. Composés d'isoxazoline antiparasitaires et pesticides
WO2015161224A1 (fr) 2014-04-17 2015-10-22 Merial, Inc. Utilisation de composés de malononitrile pour protéger des animaux contre les parasites
WO2016138339A1 (fr) 2015-02-26 2016-09-01 Merial, Inc. Formulations injectables à action prolongée comprenant un agent actif à base d'isoxazoline, méthodes et utilisations de celles-ci
WO2016187534A1 (fr) 2015-05-20 2016-11-24 Merial, Inc. Composés depsipeptidiques anthelminthiques
EP3922639A1 (fr) 2015-05-20 2021-12-15 Boehringer Ingelheim Animal Health USA Inc. Composés depsipeptidiques anthelminthiques
WO2018071535A1 (fr) 2016-10-14 2018-04-19 Merial, Inc. Composés de vinyl-isoxazoline pesticides et parasiticides
WO2018093920A1 (fr) 2016-11-16 2018-05-24 Merial, Inc. Composés depsipeptidiques anthelminthiques
WO2019036407A1 (fr) 2017-08-14 2019-02-21 Merial, Inc. Composés de pyrazole-isoxazoline à activité pesticide et parasiticide
WO2020014068A1 (fr) 2018-07-09 2020-01-16 Boehringer Ingelheim Animal Health USA Inc. Composés hétérocycliques anthelminthiques
WO2020112374A1 (fr) 2018-11-20 2020-06-04 Boehringer Ingelheim Animal Health USA Inc. Composé indazolylcyanoéthylamino, compositions associées, procédé de fabrication et procédés d'utilisation de celui-ci
WO2020191091A1 (fr) 2019-03-19 2020-09-24 Boehringer Ingelheim Animal Health USA Inc. Composés d'aza-benzothiophène et d'aza-benzofurane anthelminthiques
WO2021242581A1 (fr) 2020-05-29 2021-12-02 Boehringer Ingelheim Animal Health USA Inc. Composés hétérocycliques anthelminthiques
WO2022162016A1 (fr) 2021-01-27 2022-08-04 Intervet International B.V. Composés de cyclopropylamide contre des parasites chez les poissons
WO2022162001A1 (fr) 2021-01-27 2022-08-04 Intervet International B.V. Composés de cyclopropylamide contre des parasites chez les poissons
WO2023156938A1 (fr) 2022-02-17 2023-08-24 Boehringer Ingelheim Vetmedica Gmbh Procédé et système pour fournir un dispositif d'expédition de produit fluide

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