Classifications

• • 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
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/647—Triazoles; Hydrogenated triazoles
  • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • 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
  • A01N43/74—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 1,3
  • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• • 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
  • A01N43/74—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 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • 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
  • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P7/00—Arthropodicides
  • A01P7/02—Acaricides
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P7/00—Arthropodicides
  • A01P7/04—Insecticides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
  • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
  • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
  • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
  • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
  • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
  • A61K31/5375—1,4-Oxazines, e.g. morpholine
  • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/10—Anthelmintics
• • 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
• • 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
  • C07D401/14—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 three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
• • 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
  • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

• the present invention relates to heteroaryl compounds and pest control agents.
• This application claims priority based on Japanese Patent Application No. 2022-099256 filed in Japan on June 20, 2022, the contents of which are incorporated herein.
• Patent Document 1 states that the compound represented by formula (A) etc. can be used to suppress ectoparasites in animals.
• Patent Document 2 states that compounds represented by formula (B) etc. can be used for controlling pests.
• An object of the present invention is to provide a heteroaryl compound that has excellent pest control activity, particularly insecticidal and/or acaricidal activity, is excellent in safety, and can be synthesized industrially advantageously.
• Another object of the present invention is to provide a pest control agent, an insecticide or acaricide, an ectoparasite control agent, or an endoparasite control or extermination agent containing the above-mentioned heteroaryl compound as an active ingredient.
• Z represents an oxygen atom or a sulfur atom
• R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group
• Y 1 and Y 2 each independently represent a nitrogen atom or a group represented by CR a , where R a is a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, or Represents a substituted or unsubstituted C3-6 cycloalkyl group
• Q 1 is a substituted or unsubstituted 5-membered heteroaryl group, a substituted or unsubstituted 6-membered heteroaryl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted fused bicyclic 9- to 10-membered heteroaryl group represents a group
• Q 2 represents a substituted or unsubstituted
• R c represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, or a cyano group.
• a pest control agent containing as an active ingredient at least one selected from the group consisting of the compounds described in [1] and salts thereof.
• An insecticide or acaricide containing as an active ingredient at least one selected from the group consisting of the compounds described in [1] and their salts.
• An ectoparasite control agent containing as an active ingredient at least one selected from the group consisting of the compounds described in [1] and salts thereof.
• the heteroaryl compound of the present invention can control pests that cause problems in agricultural crops and hygiene.
• the heteroaryl compounds of the present invention can effectively control agricultural pests and mites, especially at lower concentrations.
• the heteroaryl compounds of the present invention can further effectively control ectoparasites and endoparasites that harm humans and livestock.
• the heteroaryl compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)), a salt of compound (I), or a compound represented by formula (II) ( (Hereinafter, it may be referred to as compound (II).) or a salt of compound (II).
• the term "unsubstituted” means only the core group. When “substituted” is not mentioned and only the name of the core group is listed, it means “unsubstituted” unless otherwise specified.
• substituted means that any hydrogen atom of a group serving as a core is substituted with a group (substituent) having the same or different structure from the core. Therefore, a “substituent” is another group bonded to the core group.
• the number of substituents may be one, or two or more. Two or more substituents may be the same or different.
• a term such as "C1-6" indicates that the number of carbon atoms in the group serving as a core is 1 to 6.
• This number of carbon atoms does not include the number of carbon atoms present in substituents.
• 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 permissible and has the effects of the present invention.
• C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
• Alkyl group Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, etc.
• C2-6 alkenyl group C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group;
• C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; Phenyl group, naphthyl group; Phenyl C1-6 alkyl groups such as benzyl group and phenethyl group; 3-6 membered heterocyclyl group; 3-6 membered heterocyclyl C1-6 alkyl group;
• Hydroxyl group 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; C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group; C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group; Phenoxy group, naphthoxy group; Phenyl C1-6 alkoxy groups such as benzyloxy group and phenethyloxy group; 5- to 6-membered heteroaryloxy groups such as thiazolyloxy group and pyridyloxy group; 5- to 6-membered heteroaryl C1-6 alkyloxy group such as thiazolylmethyloxy group and pyridylmethyloxy group;
• Formyl group C1-6 alkylcarbonyl groups such as acetyl group and propionyl group; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy groups and propionyloxy groups; Benzoyl group; C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group; C1-6 alkoxycarbonyloxy groups such as methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, i-propoxycarbonyloxy group, n-butoxycarbonyloxy group, t-butoxycarbonyloxy group; carboxyl group;
• Halogeno groups such as fluoro group, chloro group, bromo group, iodo group; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group; C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group; C1-6 haloalkoxy groups such as trifluoromethoxy group, 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group; C2-6 haloalkenyloxy groups such as 2-chloropropeny
• Amino group C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group, diethylamino group; Anilino group, naphthylamino group; Phenyl C1-6 alkylamino groups such as benzylamino group and phenethylamino group; formylamino group; C1-6 alkylcarbonylamino groups such as acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group; An unsubstituted or substituted aminocarbonyl group such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group,
• C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group; C1-6 haloalkylthio groups such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group; Phenylthio group, naphthylthio group; 5- to 6-membered heteroarylthio groups such as thiazolylthio group and pyridylthio group;
• C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group; Phenylsulfinyl group; 5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl groups and pyridylsulfinyl groups;
• C1-6 alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group; phenylsulfonyl group; 5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl group and pyridylsulfonyl group; C1-6 alkylsulfonyloxy groups such as methylsulfonyloxy group, ethylsulfonyloxy group, t-butylsulfonyloxy group; C1-6 haloalkylsulfonyloxy groups such as trifluoromethylsulfonyloxy group and 2,2,2-trifluoroethy
• TriC1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group; triphenylsilyl group; Cyano group; Nitro group.
• any hydrogen atom in these "substituents” may be substituted with a group having a different structure.
• the "substituent” in this case include a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, a nitro group, and the like.
• the above-mentioned "3- to 6-membered heterocyclyl group” contains 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms as ring constituent atoms.
• the heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, as long as at least one ring is a heterocycle, the remaining rings may be any of a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring.
• Examples of the "3- to 6-membered heterocyclyl group” include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.
• Examples of the "3- to 6-membered saturated heterocyclyl group” include aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group, etc.
• Examples of the "5-membered heteroaryl group” include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc. can be mentioned.
• Examples of the "6-membered heteroaryl group” include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
• Examples of "5- to 6-membered partially unsaturated heterocyclyl group” include pyrrolinyl group, dihydrofuranyl group, dihydrothiophenyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group, thiazolinyl group, isothiazolinyl group, etc.
• a 5-membered partially unsaturated heterocyclyl group; a 6-membered partially unsaturated heterocyclyl group such as a dihydropyranyl group can be mentioned.
• [Z] Z in formula (I) represents an oxygen atom or a sulfur atom, preferably an oxygen atom.
• R 1 , R 2 , R 3 , R 4 ] R 1 , R 2 , R 3 and R 4 in formula (I) each independently represent a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
• the "C1-6 alkyl group" in R 1 , R 2 , R 3 and R 4 may be linear or branched.
• Examples of the "C1-6 alkyl group" for R 1 , R 2 , R 3 and R 4 include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i- Examples include propyl group, i-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, and i-hexyl group.
• Substituents on the "C1-6 alkyl group" in R 1 , R 2 , R 3 and R 4 include halogeno group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6R alkyl group, Any one of a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, a cyano group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group A phenyl group substituted with one or more substituents; with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group a substituted 5-membered heteroaryl group; or substituted with one or more substituents
• R 1 , R 2 , R 3 and R 4 are preferably a hydrogen atom or unsubstituted C1-6 alkyl, and more preferably a hydrogen atom or a methyl group.
• [Y 1 , Y 2 ] Y 1 and Y 2 in formula (I) each independently represent a nitrogen atom or a group represented by CR a .
• R a represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group.
• R a examples include the same groups as those shown in R 1 , R 2 , R 3 and R 4 .
• halogeno group examples include a fluoro group, a chloro group, a bromo group, an iodo group, and the like.
• Examples of the "C3-6 cycloalkyl group" for R a include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
• Substituents on the "C3-6 cycloalkyl group" in R a include halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 6-cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy a phenyl group substituted with one or more substituents; any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; A 5-membered heteroaryl group substituted with the above substituents; or any one or more of a C1-6 alkyl group, a C
• Y 1 and Y 2 in formula (I) are each independently preferably a nitrogen atom or CH, and more preferably Y 1 is CH and Y 2 is a nitrogen atom. .
• Q 1 in formula (I) is a substituted or unsubstituted 5-membered heteroaryl group, a substituted or unsubstituted 6-membered heteroaryl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted fused bicyclic group Indicates a 9- to 10-membered heteroaryl group.
• Q 2 in formula (I) represents a substituted or unsubstituted 5-membered heteroaryl group or a substituted or unsubstituted 6-membered heteroaryl group.
• Examples of the "5-membered heteroaryl group" in Q 1 and Q 2 include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, and a thiadiazolyl group. group, tetrazolyl group, etc.
• Examples of the "6-membered heteroaryl group" in Q 1 and Q 2 include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
• the "fused bicyclic 9-membered heteroaryl group" in Q 1 includes an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, an indazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzisoxazolyl group, and a benzothiazolyl group. and benzisothiazolyl group.
• Examples of the "fused bicyclic 10-membered heteroaryl group" in Q 1 include a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a phthalazinyl group, a quinazolinyl group, and a quinoxalinyl group.
• the substituents on the "fused bicyclic 9- to 10-membered heteroaryl group” and the substituents on the "5-membered heteroaryl group” or “6-membered heteroaryl group” in Q2 include a halogeno group, C1- 6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, C1-6 haloalkylthio group, C1-6 haloalkylsulfonyl group, phenyl group, 5 membered heteroaryl group, 6-membered heteroaryl group, cyano group, amino group, aminocarbonyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group A
• C1-6 haloalkylthio group examples include a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group.
• C1-6 haloalkylsulfonyl group examples include a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group.
• Q 1 in formula (I) preferably represents a substituted or unsubstituted phenyl group.
• the substituent on the phenyl group in Q 1 is selected from the group consisting of a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, a C1-6 haloalkylthio group, a C1-6 haloalkylsulfonyl group, and an amino group. It is preferable that at least one of them is selected.
• the number of substituents on the phenyl group in Q 1 is preferably 0 to 3, more preferably 2 or 3, and even more preferably 2.
• Q 2 in formula (I) preferably represents a substituted or unsubstituted 6-membered heteroaryl group, and more preferably represents a substituted or unsubstituted pyridyl group or a substituted or unsubstituted pyrimidinyl group.
• the substituent on the 6-membered heteroaryl group in Q 2 is preferably a halogeno group, a C1-6 haloalkoxy group, a cyano group, or an aminocarbonyl group; More preferred.
• the substituent on the pyridyl group in Q 2 is preferably a halogeno group, a cyano group, or an aminocarbonyl group, and more preferably a halogeno group or a cyano group.
• the substituent on the pyrimidinyl group in Q 2 is preferably a halogeno group or a C1-6 haloalkoxy group.
• a in formula (I) represents a single bond or a substituted or unsubstituted methylene group.
• R b is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkyl group Represents a carbonyl group or a substituted or unsubstituted C1-6 alkoxycarbonyl group.
• R b examples include the same groups as those for R 1 , R 2 , R 3 and R 4 .
• Examples of the "substituted or unsubstituted C3-6 cycloalkyl group" for R b include the same groups as those shown for R a .
• Examples of the "C1-6 alkoxy group" in R b include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group, etc. can be mentioned.
• C1-6 alkylcarbonyl group examples include acetyl group, propionyl, n-propylcarbonyl group, i-propylcarbonyl group, n-butylcarbonyl group, t-butylcarbonyl group, and the like.
• Examples of the "C1-6 alkoxycarbonyl group" in R b include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group, etc. can.
• Substituents on the "C1-6 alkyl group", “C1-6 alkoxy group”, “C1-6 alkylcarbonyl group”, or “C1-6 alkoxycarbonyl group” in R b include a halogeno group, a hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group; C1-6 alkyl group, C1-6 alkoxy group, A phenyl group substituted with one or more substituents of a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 A 5-membered heteroaryl group substituted with any one or more substituents of a haloalkyl group or a C1-6 haloal
• Substituents on the "C3-6 cycloalkyl group" in R b include halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3 ⁇ 6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 halo A phenyl group substituted with any one or more substituents of an alkoxy group; Any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group a 5-membered heteroaryl group substituted with three or more substituents; or one or more of a C1-6 alky
• R c represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, or a cyano group.
• R c examples include the same groups as those shown in R 1 , R 2 , R 3 and R 4 .
• R c examples include the same groups as those shown in R a .
• Substituents on the "C1-6 alkyl group" in R c include halogeno group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group; Substituted with one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group phenyl group; 5-membered heteroaryl substituted with one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group or a 6-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C
• Substituents on the "C3-6 cycloalkyl group” or "phenyl group” in R c include halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 Haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or a phenyl group substituted with any one or more substituents of a C1-6 haloalkoxy group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy a 5-membered heteroaryl group substituted with any one or more substituents; or a C1-6 alkyl group
• R c is preferably a hydrogen atom or a cyano group, and more preferably a hydrogen atom.
• Substituents on the "methylene group" in A or B include halogeno group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6 Member heteroaryl group, cyano group; Phenyl substituted with one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or A 6-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno
• A is a methylene group
• B is preferably an oxygen atom.
• the salt of compound (I) and the salt of compound (II) are not particularly limited as long as they are agriculturally and horticulturally acceptable salts.
• Examples of the salt of compound (I) and the salt of compound (II) include salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium, and potassium; Examples include salts of alkaline earth metals such as calcium and magnesium; salts of transition metals such as iron and copper; ammonia; salts of organic bases such as triethylamine, tributylamine, pyridine and hydrazine.
• the method for producing compound (I), the salt of compound (I), compound (II), and the salt of compound (II) is not particularly limited.
• Compound (I), a salt of Compound (I), Compound (II), and a salt of Compound (II) can be obtained by known production methods described in Examples and the like.
• the salt of compound (I) or the salt of compound (II) can be obtained from compound (I) or compound (II) by a known method.
• reaction scheme 1 For example, among compound (I), the method for preparing the compound represented by formula (Ia) (hereinafter sometimes referred to as the compound of formula (Ia)) can be shown in reaction scheme 1 below. .
• the compound of formula (Ia) is a compound represented by formula (III) (hereinafter sometimes referred to as a compound of formula (III)) and a compound represented by formula (IV) (hereinafter referred to as formula (IV)). ) in the presence of an organic base (eg, triethylamine, diisopropylethylamine, etc.) and reacting at a temperature within the range of 0 to 100°C. This compound can then be isolated and, if necessary, purified using techniques well known in the art, such as chromatography.
• an organic base eg, triethylamine, diisopropylethylamine, etc.
• This compound can then be isolated and, if necessary, purified using techniques well known in the art, such as chromatography.
• the symbols in formula (Ia), formula (III), and formula (IV) have the same meanings as those in formula (I).
• Compounds of formula (IV) are commercially available or can be synthesized by known methods. For
• Reaction scheme 2 Among compounds (I), a method for preparing a compound represented by formula (Ib) (hereinafter sometimes referred to as a compound of formula (Ib)) can be shown in Reaction Scheme 2 below.
• a compound of formula (Ib) can be prepared by reacting a compound of formula (Ia) in the presence of Lawesson's reagent at a temperature within the range of 0 to 100°C. This compound can then be isolated and, if necessary, purified using techniques well known in the art, such as chromatography.
• the symbols in formula (Ib) have the same meanings as those in formula (I).
• Reaction scheme 3 A method for preparing the compound of formula (III) can be shown in Reaction Scheme 3 below.
• the compound of formula (III) is a compound represented by formula (V) (hereinafter sometimes referred to as the compound of formula (V)) in the presence of an acid (for example, trifluoroacetic acid, hydrochloric acid, etc.), It can be prepared by deprotection at a temperature within the range of ⁇ 50°C. In this case, the resulting compound of formula (III) may be a salt. This compound can then be isolated and, if necessary, purified using techniques well known in the art, such as chromatography.
• the symbols in formula (V) have the same meanings as those in formula (I). Boc means tert-butoxycarbonyl group.
• Reaction scheme 4 A method for preparing compounds of formula (V) can be shown in Reaction Scheme 4 below.
• the compound of formula (V) is a compound represented by formula (VI) (hereinafter sometimes referred to as a compound of formula (VI)) and a compound represented by formula (VII) (hereinafter referred to as formula (VII)). ) under acidic conditions (for example, a mixed solvent of acetic acid and 1,4-dioxane) and reacting at a temperature in the range of about 20 to 100°C. This compound can then be isolated and, if necessary, purified using techniques well known in the art, such as chromatography.
• the symbols in formula (VI) and formula (VII) have the same meanings as those in formula (I).
• Compounds of formula (VII) are commercially available or can be synthesized by known methods. For example, it can be prepared using the method described in Cited Document 1 or Cited Document 2.
• Reaction scheme 5 A method for preparing compounds of formula (VI) can be shown in Reaction Scheme 5 below.
• the compound of formula (VI) is prepared by combining the compound of formula (VIII) (hereinafter sometimes referred to as the compound of formula (VIII)) with the compound of formula (IX) in a suitable solvent such as dichloromethane. It can be prepared by mixing compounds (hereinafter sometimes referred to as compounds of formula (IX)) and reacting at reflux temperature. This compound is preferably subjected to the next reaction without being isolated.
• the symbols in formula (VIII) and formula (IX) have the same meanings as those in formula (I).
• Compounds of formula (IX) are commercially available or can be synthesized by known methods. For example, it can be prepared using the method described in Cited Document 1 or Cited Document 2.
• Reaction scheme 6 A method for preparing the compound of formula (VIII) can be shown in Reaction Scheme 6 below.
• the compound of formula (VIII) can be prepared by amidating the compound represented by formula (X) (hereinafter sometimes referred to as the compound of formula (X)) using a compound that serves as a nitrogen source.
• a method can be mentioned in which the compound of formula (X) is induced into an acid halide and then amidated using ammonia as a nitrogen source.
• Other examples include a method of deriving the compound of formula (X) into an ester and amidating it using ammonia as a nitrogen source.
• a dehydration condensation reaction using a condensing agent which is a general method for preparing an amide bond, can also be mentioned.
• condensing agent examples include dicyclohexylcarbodiimide, diisopropylcarbodiimide, and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride.
• a condensation aid may also be added if necessary, and examples of the condensation aid include 1-hydroxybenzotriazole and 1-hydroxy-7-azabenzotriazole. This compound can then be isolated and, if necessary, purified using techniques well known in the art, such as chromatography.
• symbols in formula (X) have the same meanings as those in formula (I).
• Reaction scheme 7 A method for preparing compounds of formula (X) can be shown in Reaction Scheme 7 below.
• the compound of formula (X) is obtained by preparing a compound of formula (XI) (hereinafter sometimes referred to as the compound of formula (XI)) using di-t-butyl dicarbonate (Boc 2 O) or the like. It can be prepared by Boc protection. This compound can then be isolated and, if necessary, purified using techniques well known in the art, such as chromatography.
• the symbols in formula (XI) have the same meanings as those in formula (I).
• Compounds of formula (XI) are commercially available or can be synthesized by known methods. For example, it can be prepared using Reaction Scheme 8 or Reaction Scheme 9 shown below.
• reaction scheme 8 (Reaction scheme 8) Among compounds (XI), the method for preparing the compound represented by formula (XI-a) (hereinafter sometimes referred to as the compound of formula (XI-a)) is shown in reaction scheme 8 below. Can be done.
• the compound of formula (XI-a) is a compound of formula (XII-a) (hereinafter referred to as the compound of formula (XII-a)) in a suitable solvent such as ethanol, water, or aqueous ethanol. ) and the compound represented by formula (XIII-a) (hereinafter sometimes referred to as the compound of formula (XIII-a)) in the presence of an inorganic base (e.g., sodium hydroxide, sodium acetate, etc.) It can be prepared by pre-mixing and reacting at a temperature within the range of 0°C to room temperature. This compound can then be isolated and, if necessary, purified using techniques well known in the art, such as chromatography.
• an inorganic base e.g., sodium hydroxide, sodium acetate, etc.
• A' in formula (XI-a) and formula (XII-a) represents a single bond
• B' represents an oxygen atom or a sulfur atom
• other symbols are those in formula (I). Indicates the same meaning as .
• the symbols in formula (XIII-a) have the same meanings as those in formula (I).
• Compounds of formula (XII-a) are commercially available or can be synthesized by known methods.
• Compounds of formula (XIII-a) are commercially available or can be synthesized by known methods.
• reaction scheme 9 (Reaction scheme 9) Among compounds (XI), the method for preparing the compound represented by formula (XI-b) (hereinafter sometimes referred to as the compound of formula (XI-b)) is shown in reaction scheme 9 below. Can be done.
• the compound of formula (XI-b) is prepared by combining a compound of formula (XII-b) (hereinafter sometimes referred to as a compound of formula (XII-b)) with a compound of formula (XII-b) in a suitable solvent such as acetonitrile.
• XIII-b) (hereinafter sometimes referred to as the compound of formula (XIII-b)) are mixed in the presence of an inorganic base (e.g. potassium tert-butoxide) and reacted at reflux temperature. It can be prepared by letting Deprotection is then carried out in the presence of an acid (e.g.
• A" in formula (XI-b) and formula (XIII-b) represents a substituted or unsubstituted methylene group
• formula (XI-b), (XII-b), and formula (XIII-b B” in ) represents an oxygen atom or a sulfur atom
• R 6 in formula (XII-b) represents a C1-6 alkyl group
• other symbols have the same meanings as those in formula (I). show.
• Compounds of formula (XII-b) are commercially available or can be synthesized by known methods.
• Compounds of formula (XIII-b) are commercially available or can be synthesized by known methods.
• the heteroaryl compound of the present invention (hereinafter referred to as "the compound of the present invention”) has an excellent control effect on pests such as various agricultural pests and mites that affect the growth of plants. Furthermore, the compound of the present invention has little phytotoxicity to agricultural and horticultural crops, and has low toxicity to fish and warm-blooded animals, so it is a highly safe substance. Therefore, it is useful as an active ingredient in insecticides or acaricides. Furthermore, in recent years, many insect pests such as diamondback moths, planthoppers, leafhoppers, and aphids have developed resistance to various existing chemicals, resulting in the lack of efficacy of these chemicals.Therefore, there is a need for chemicals that are effective against resistant insect pests. ing. The compounds of the present invention exhibit excellent control effects not only on susceptible strains, but also on various resistant strains of insect pests, and furthermore against acaricide-resistant strains of mites.
• the compound of the present invention has an excellent control effect on ectoparasites and endoparasites that are harmful to humans and animals. It is also a highly safe substance as it has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient in agents for controlling ectoparasites and endoparasites.
• the compounds of the present invention exhibit efficacy at all developmental stages of organisms to be controlled, and exhibit excellent control effects against eggs, nymphs, larvae, pupae, and adults of mites and insects, for example.
• Pest control agent contains as an active ingredient at least one selected from the group consisting of the compound of the present invention and its salt.
• the amount of the compound of the present invention contained in the pest control agent of the present invention is not particularly limited as long as it exhibits a pest control effect.
• Pest control agents are agents for controlling harmful organisms, and include insecticides or acaricides, ectoparasite control agents, endoparasite control or exterminators, and the like.
• insecticide or acaricide of the present invention contains as an active ingredient at least one selected from the group consisting of the compound of the present invention and its salt.
• the amount of the compound of the present invention contained in the insecticidal or acaricidal agent of the present invention is not particularly limited as long as it exhibits an insecticidal or acaricidal effect.
• the pest control agent, insecticide or acaricide of the present invention can be applied to cereals; vegetables; root vegetables; tubers; flowers; fruit trees; ornamental plants, trees such as tea, coffee and cacao; grasses; Turf; preferably used for plants such as cotton.
• the pest control agent, insecticide or acaricide of the present invention can be applied to any plant such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings, etc. It may be used in the following areas.
• the pest control agent, insecticide or acaricide of the present invention is not particularly limited depending on the species of the plant to which it is applied.
• Examples of plant species include original species, varieties, improved varieties, cultivated varieties, mutants, hybrids, and genetically modified plants (GMOs).
• the pest control agent of the present invention can be used for seed treatment, foliage spraying, soil application, water surface application, etc. in order to control various agricultural pests and mites.
• Agrotis ipsilon, Agrotis segetum e.g., Helicoverpa spp., Helicoverpa armigera, Helicoverpa assulta, cotton ballworm (Helicoverpa zea); e.g., Helicoverpa spp.
• Thysanoptera pests (a) Phlaeothripidae, for example, Ponticulothrips diospyrosi; (b) Thripidae, such as Frankliniella spp., Frankliniella intonsa, and Frankliniella occidentalis; for example, Thrips spp. Thrips palmi, Thrips tabaci; others, Heliothrips haemorrhoidalis, Scirtothrips dorsalis.
• Phlaeothripidae for example, Ponticulothrips diospyrosi
• Thripidae such as Frankliniella spp., Frankliniella intonsa, and Frankliniella occidentalis
• Thrips spp. Thrips palmi Thrips tabaci
• others Heliothrips haemorrhoidalis, Scirtothrips dorsalis.
• Pests of the order Hemiptera A member of the family Delphacidae, for example, Laodelphax striatella , brown planthopper (Nilaparvata lugens), black-throated planthopper (Perkinsiella saccharicida), and white-bellied planthopper (Sogatella furcifera).
• B Clypeorrhyncha
• a Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca onukii, Empoasca spp. of the family Cicadellidae, for example Empoasca spp. Empoasca sakaii; Other leafhoppers: Arboridia apicalis, Balclutha saltuella, Epicanthus stramineus, Macrosteles striifrons, Nephotettix cinctinceps ).
• C Heteroptera
• Alydidae for example, Riptortus clavatus
• a member of the Coreidae family for example, Cletus punctiger , Leptocorisa chinensis
• Lygaeidae such as Blissus leucopterus, Cavelerius saccharivorus, Togo hemipterus
• Members of the Miridae family such as Halticus insularis, Lygus lineolaris, Cotton Free Hopper (Psuedatomoscelis seriatus), Stenodema sibiricum, and Stenotus rubrovitttatus. ), Trigonotylus caelestialium;
• Pentatomidae such as Nezara spp., Nezara antennata, Nezara viridula; for example, Eysarcoris spp. , Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, others, Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, and Eysarcoris ventralis.
• Halyomorpha halys Piezodorus hybneri, Plautia crossota, Scotinophora lurida;
• Pyrrhocoridae for example, Dysdercus cingulatus;
• Rhopalus musculatus of the family Rhopalidae for example;
• Scutelleridae for example, Eurygaster integriceps;
• Tingidae for example Stephanitis nashi.
• (D) Sternorrhyncha (a) Adelgidae, for example, the larch aphid (Adelges laricis); (b) Bemisia argentifolii, Bemisia tabaci of the family Aleyrodidae, such as Bemisia spp.; other, Aleurocanthus spiniferus, citrus whitefly; (Dialeurodes citri), whitefly (Trialeurodes vaporariorum); (c) Aphis craccivora, Aphis fabae, Aphis forbesi, and Aphis gossypii of the Aphidae family, such as Aphis spp.
• Rhopalosiphum spp. corn aphid (Rhopalosiphum maidis), wheat aphid (Rhopalosiphum padi)
• Dysaphis spp. Dysaphis plantaginea, Dysaphis radicola;
• Aphids Macrosiphum euphorbiae
• Myzus spp. Myzus cerasi, Myzus persicae, Myzus varians; other pea aphids (Macrosiphum euphorbiae); Acyrthosiphon pisum), Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Chaetosiphon fragaefolii, Hyalopterus pruni, Hyperomyzus lactuc ae ), Lipaphis erysimi, Megoura viciae, Metopolophium dirhodum, Nasonovia ribis-nigri, Phorodon humuli, Schizaphis graminum ), wheat aphid (Sitobion avenae), comic cane aphid (Toxoptera aurantii);
• Unaspis euonymi Unaspis yanonensis; others, Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, Pseudaonidia paeoniae ); (f) family Margarodidae, such as Drosicha diverenta, Icerya purchasi; (g) of the family Phylloxeridae, for example Viteus vitifolii; (h) Planococcus citri, Planococcus kuraunhiae of the Pseudococcidae family, such as Planococcus spp.; other Phenacoccus solani , Pseudococcus comstocki; (i) Psylla mali, Psylla pyrisuga of the family Psyllidae, such as Psylla spp.; and other, Diaphorina citri.
• Pests of the suborder Polyphaga (a) of the family Anobiidae, for example, the tobacco beetle (Lasioderma serricorne); (b) family Attelabidae, such as Byctiscus betulae, Rhynchites heros; (c) Bostrichidae, for example, Lyctus brunneus; (d) of the family Brentidae, for example, Cylas formicarius; (e) Buprestidae, for example, Agrilus sinuatus; (f) Cerambycidae, such as Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, and Xylotrechus pyrrhoderus; (g) Chrysomelidae, e.g.
• Bruchus spp. pea weevil (Bruchus pisorum), broad bean weevil (Bruchus rufimanus); e.g. Diabrotica spp., northern corn; rootworm (Diabrotica barberi), southern corn rootworm (Diabrotica undecimpunctata), western corn rootworm (Diabrotica virgifera); e.g., Phyllotreta spp.
• Coccinellidae for example, Epilachna spp., Epilachna varivestis, Epilachna vigintioctopunctata;
• Curculionidae e.g. Anthonomus spp., boll weevil (Anthonomus grandis), pear weevil (Anthonomus pomorum); e.g. of Sitophilus spp.
• Pests of Diptera Brachycera
• a family Agromyzidae, for example, Liriomyza spp., Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza trifolii; Others, Chromatomyia horticola, Agromyza oryzae;
• Anthomyiidae such as Delia spp., Delia platura, Delia radicum; other Pegomya cunicularia;
• Ephydridae for example, Hydrellia griseola
• Psilidae for example, Psila rosae
• Bactrocera cucurbitae Bactrocera dorsali
• Nematocera (a) Family Cecidomyiidae, such as Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor, and Sitodiplosis mosellana.
• Pests of the order Orthoptera (a) Acrididae, such as Schistocerca spp., Schistocerca americana, Schistocerca gregaria; other, Australian locust (Chortoicetes terminifera),ixie locust (Dociostaurus maroccanus), brown locust (Locusta migratoria), brown locust (Locustana pardalina), red kite locust (Nomadacris septemfasciata), brown locust (Oxya yezoensis); (b) Gryllidae, for example, European house cricket (Acheta domestica), Enma cricket (Teleogryllus emma); (c) Molecular family (Gryllotalpidae), for example, Molecular mole (Gryllotalpa orientalis); (d) Members of the family Tettigoniidae, such as Tachycines asynamorus.
• Acrididae such as Schisto
• Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus ludeni of Tetranychus spp. Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Tetranychus viennensis, Tetranychus evansi; for example, Aponychus corpuzae, Aponychus spp.
• Aponychus firmianae for example, Sasanychus akitanus, Sasanychus pusillus, of the genus Sasanychus spp.; for example, Aponychus firmianae, of the genus Shizotetranychus spp. Shizotetranychus celarius), Shizotetranychus longus, Shizotetranychus miscanthi, Shizotetranychus recki, Willow spider mite (Shizotetranychus schizopus); Others, Tetranychina harti, Tuckerella pavoniformis ), Caeus spider mite (Yezonychus sapporensis);
• Aceria paradianthi Aceria tiyingi, tulip rust mite, Aceria zoysiea; for example, Eriophyes spp., Eriophyes chibaensis, Eriophyes emarginatae); e.g. Aculops spp., tomato rust mite (Aculops lycopersici), orange rust mite (Aculops pelekassi); e.g. Aculus spp., peach rust mite (Aculus fockeui), apple rust mite (Aculus).
• the pest control agent of the present invention may contain other active ingredients such as fungicides, insecticides/acaricides, nematicides, soil insecticides, etc.; plant regulators, synergists, fertilizers, soil conditioners, and animals. It may be mixed or used in combination with feed etc.
• a combination of the compound of the present invention and other active ingredients can be expected to have a synergistic effect with respect to insecticidal, acaricidal, and nematocidal activities.
• the synergistic effect can be confirmed by Colby's formula (Colby. SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pp. 20-22, 1967) according to a standard method.
• Acetylcholinesterase (AChE) inhibitor organophosphorus
• Acephate Azamethiphos
• Azinphos-ethyl Azinphosmethyl
• Cadusafos Chlorethoxyfos
• Chlorfenvinphos Chlormephos
• Chlorpyrifos Chlorpyrifos-methyl
• Coumaphos Cyanophos
• Cyanophos Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoate ( Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate Fosthiazate), Heptenophos, Imicyafos, Isofenphos, Is
• GABAergic chloride ion (chloride ion) channel blockers Chlordane, Endosulfan; Ethiprole, Fipronil. Acetoprole, Camphechlor, Dienochlor, Heptachlor, Pyrafluprole, Pyriprole; Flufiprole.
• Kappa-Bifenthrin Biopermethrin, Chloroprallethrin, Dimefluthrin, Fenfluthrin, Fenpirithrin, Flufenprox, Heptaflu Heptafluthrin, Meperfluthrin, epsilon-Metofluthrin, Momfluorothrin, epsilon-Momfluorothrin, trans-Permethrin, Profluthrin , Protrifenbute, kappa-Tefluthrin, Terallethrin, Tetramethylfluthrin; Bioethanomethrin. (3B) Sodium channel modulators (DDTs) DDT, Methoxychlor.
• Nicotinic acetylcholine receptor (nAChR) competitive modulators Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam; Nicotine (Nicotine); Sulfoxaflor; Flupyradifurone; Triflumezopyrim. Nithiazine; Dicloromezotiaz, Flupyrimin.
• Nicotinic acetylcholine receptor (nAChR) allosteric modulators Spinetoram, Spinosad.
• Glutamatergic chloride ion channel (GluCl) allosteric modulator Abamectin, Emamectin, Emamectin-benzoate, Lepimectin, Milbemectin. Doramectin, Eprinomectin, Ivermectin, Moxidectin, Selamectin.
• Other non-specific (multisite) inhibitors Methyl bromide, alkyl halides; Chloropicrin; Sodium aluminum fluoride, sulfuryl fluoride ( Sulfuryl fluoride); Borax, Boric acid, Disodium octaborate, Sodium borate, Sodium metaborate; Tartar Dazomet, Metam, Metam Sodium, Metam Potassium.
• Mite growth inhibitors Clofentezine, Diflovidazin, Hexythiazox; Etoxazole.
• Bt crop proteins Microbial-derived insect midgut membrane disrupting agent Bt subsp. israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. tenebrionis; proteins contained in Bt crops (Bt crop proteins): Cry1Ab, Cry1Ac , Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1; Bacillus sphaericus.
• Chitin biosynthesis inhibitor type 0 Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron ), Noviflumuron, Teflubenzuron, Triflumuron. Fluazuron.
• Chitin biosynthesis inhibitor type 1 Buprofezin.
• Molting inhibitor Cyromazine Molting hormone (ecdysone) receptor agonists Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide.
• anthelmintic agents that can be mixed or used in combination with the pest control agent of the present invention are shown below.
• Salicylanilide series closantel, oxyclozanide, lafoxanide, niclosamide;
• Other anthelmintics
• fungicides that can be mixed or used in combination with the pest control agent of the present invention are shown below.
• A) Inhibitor of nucleic acid synthesis metabolism A1) RNA polymerase I inhibitor benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl ); ofurace.
• DNA/RNA biosynthesis inhibitors hymexazole, octhilinone A4) DNA topoisomerase type II inhibitor oxolinic acid.
• B Agents that act on the cytoskeleton and motor proteins B1) to B3) Inhibition of ⁇ -tubulin polymerization Benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate methyl (thiophanate-methyl), diethofencarb, zoxamide, ethaboxam. Chlorfenazole, debacarb, trichlamide, zarilamid. B4) Cell division (point of action unknown) pencycuron. B5) Delocalization of spectrin-like proteins Fluopicolide, fluopimomide. B6) Actin/myosin/fimbrin function phenamacryl, metrafenone, pyriofenone.
• C1 Respiratory inhibitor C1
• Complex I NADH oxidoreductase diflumetorim, tolfenpyrad, fenazaquin.
• Complex II Succinate dehydrogenase benodanil, flutolanil, mepronil; isofetamid; fluopyram; cyclobutrifluram; fenfuram; carboxy carboxin, oxycarboxin; thifluzamide; benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, impyr inpyrfluxam, isopyrazam, penflufen, penthiopyrad, sedaxane; isoflucypram; pydiflumetofen; boscalid; pyraziflumid .
• Furmecyclox. C3) Complex III Cytochrome bc1 (ubiquinol oxidase) Qo site (cyt b gene) azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; mandestrobin (mandestrobin); pyraclostrobin, pyrametostrobin, triclopyricarb; kresoxim-methyl, trifloxystrobin; dimoxystrobin, phenaminest fenaminstrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidone; pyribencarb; methyltetraprole.
• Cytochrome bc1 ubiquinol oxidase
• Qo site cyt b gene
• D Inhibitor of amino acid and protein synthesis
• Methionine biosynthesis cgs gene
• Cyprodinil mepanipyrim, pyrimethanil
• D2 Protein synthesis (ribosome translation termination stage) Blasticidin-S D3)
• D4 Protein synthesis (ribosome translation initiation stage) Kasugamycin, kasugamycin hydrochloride, streptomycin.
• D5) Protein synthesis (ribosome polypeptide elongation stage) Oxytetracycline.
• E Signal transduction inhibitor
• E1 Signal transduction (mechanism of action unknown) quinoxyfen, proquinazid.
• E2 MAP/histidine kinase (os-2, HOG1) in osmotic signal transduction
• E3 MAP/histidine kinases (os-1, Daf1) in osmotic signal transduction chlozolinate, dimethachlone, iprodione, procymidone, vinclozolin.
• F Agents that inhibit lipid biosynthesis or transport/cell membrane structure or function
• F2 Phospholipid biosynthesis, methyltransferases edifenphos, iprobenfos, pyrazophos; isoprothiolane.
• F3) Cellular peroxidation biphenyl, chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl; etridiazole.
• F4 Cell membrane permeability, fatty acids iodocarb, propamocarb, propamocarb hydrochloride, prothiocarb.
• (G) Inhibitor of sterol biosynthesis in cell membrane G1) Demethylase at position C14 of sterol biosynthesis (erg11/cyp51) triforine; pyrifenox, pyrisoxazole; fenarimol, nuarimol; imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole; azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, etaconazole ( etaconazole), fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, mefen trifluconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole
• H Inhibitor of cell wall biosynthesis H4) Chitin synthase polyoxin. Polyoxorim. H5) Cellulose synthase dimethomorph, flumorph, pyrimorph; benthiavalicarb, iprovalicarb, valifenalate; mandipropamid.
• I Inhibitor of cell wall melanin synthesis
• I1 Reductase of melanin biosynthesis fthalide; pyroquilon; tricyclazole.
• I2) Dehydratase of melanin biosynthesis carpropamid; diclocymet; fenoxanil.
• I3) Polyketide synthase tolprocarb for melanin biosynthesis.
• P Agents that induce host plant resistance P1 to P3) Salicylic acid signal transduction acibenzolar-S-methyl; probenazole; tiadinil, isotianil. P4) Polysaccharide elicitor laminarin. P5) Anthraquinone elicitor extract from Reynoutria sachalinensis. P6) Microbial elicitor Bacillus mycoides isolate J; cell walls of Saccharomyces cerevisiae strain LAS117. P7) Phosphonates fosetyl-Al; phosphorous acid and salts; fosetyl-K, fosetyl-Na. P8) Salicylic acid related dichlobentiazox
• (M) Agents that exhibit multi-site contact activity Copper (different salts), basic copper sulfate, Bordeaux mixture, copper hydroxide, copper Copper naphthenate, copper oxychloride, copper sulfate, cuprous oxide, oxine-copper; sulphur, lime sulfur; amobam, ferbam, mancozeb, maneb, metiram, propineb, thiram, zinc thiazole, zineb, ziram ); captan, captafol, folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, guazatine acetates, iminoctadine (iminoctadine), iminoctadine triacetate, iminoctadine trialbesilate; anilazine; dithianon; chinomethionat; fluorimide; methasulfocarb. dazomet, cufraneb, mancopper, polycarba
• BM01 Biopesticides with multiple mechanisms of action/Pesticides of biological origin Extract from the cotyledons of lupine plantlets; Extract from Swinglea glutinosa; Gosei Kayupte ( extract from Melaleuca alternifolia (tea treeoil); plant oils (mixtures): eugenol, geraniol, thymol.
• Trichoderma atroviride strain I-1237 Trichoderma atroviride strain LU132, Trichoderma atroviride strain SC1 ( Trichoderma atroviride strain SC1), Trichoderma atroviride strain SKT-1, Trichoderma atroviride strain 77B; Trichoderma asperellum strain T34, Trichoderma asperellum strain kd; Trichoderma harzianum strain T-22; Trichoderma virens strain G-41; Gliocladium catenulatum strain J1446; Clonostachys rosea strain CR-7; Coniothyrium minitans strain CON/M/91-08; Talaromyces flavus strain SAY-Y-94-01; Saccharomyces cerevisae strain LAS02; Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens strain F
• plant regulators that can be mixed or used in combination with the pest control agent of the present invention are shown below. Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as aviglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiol, 1 -Naphthylacetamide, etyclozate, chloroxyfonac, maleic hydrazide, 2,3,5-triiodobenzoic acid,
• the ectoparasiticide of the present invention contains as an active ingredient at least one selected from the group consisting of the compounds of the present invention and salts thereof.
• the amount of the compound of the present invention contained in the ectoparasite control agent of the present invention is not particularly limited as long as it exhibits an ectoparasite control effect.
• Host animals to be treated with the ectoparasite control agent of the present invention include humans, livestock mammals (e.g., cows, horses, pigs, sheep, goats, etc.), experimental animals (e.g., mice, rats, gerbils, etc.). ), companion animals (e.g.
• hamsters guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.
• wild and zoo mammals monkeys, foxes, deer, buffalo, etc.
• poultry turkeys, ducks, chickens, etc.
• warm-blooded animals such as quail, geese, etc.
• pet birds pigeons, parrots, mynahs, sparrows, parakeets, Japanese pine, canaries, etc.
• fish such as salmon, trout, and carp.
• Other examples include bees, stag beetles, and rhinoceros beetles.
• the ectoparasite control agent of the present invention can be applied by known veterinary techniques (topically, orally, parenterally, or subcutaneously). Methods include oral administration to animals using tablets, capsules, feed, etc.; administration to animals via immersion solutions, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); oil-based or A method of locally administering an aqueous solution by spraying, pour-on, spot-on, etc.; Knead the ectoparasiticide into resin, mold the kneaded product into a suitable shape such as a collar or ear tag, and apply it to the animal. Examples include a method of wearing the device and administering it locally;
• Ectoparasites live in and on host animals, especially warm-blooded animals. Specifically, they live by parasitizing the back, armpits, lower abdomen, inner thighs, etc. of host animals, and obtain nutrients such as blood and dander from the animals. Examples of external parasites include mites, lice, fleas, mosquitoes, stable flies, and black flies. Specific examples of ectoparasites that can be controlled by the ectoparasiticide of the present invention are shown below.
• Siphonaptera Fleas of the Pulicidae family e.g. Ctenocephalides spp., Ctenocephalides canis, Ctenocephalides felis; fleas of the Tungidae family, Ceratophyllidae fleas, Ceratophyllidae. (Leptopsyllidae) fleas.
• Hemiptera Hemiptera.
• the endoparasite controlling or exterminating agent of the present invention contains as an active ingredient at least one selected from the group consisting of the compounds of the present invention and salts thereof.
• the amount of the compound of the present invention contained in the endoparasite control or extermination agent of the present invention is not particularly limited as long as it exhibits an endoparasite control effect.
• the parasites targeted by the endoparasite control or extermination agent of the present invention parasitize host animals, particularly warm-blooded animals and fish (endoparasites).
• Host animals for which the endoparasite control or extermination agent of the present invention is effective include humans, livestock mammals (e.g., cows, horses, pigs, sheep, goats, etc.), and laboratory animals (e.g., mice, rats, gerbils, etc.).
• companion animals e.g.
• hamsters guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.
• wild and zoo mammals monkeys, foxes, deer, buffaloes, etc.
• poultry turkeys, ducks, chickens, quails, etc.
• warm-blooded animals such as pet birds (pigeons, parrots, mynahs, sparrows, parakeets, Japanese pine, canaries, etc.); and fish such as salmon, trout, and carp.
• Parasites to be controlled or exterminated include the following: (1) Nematodes of the order Dioctophymatida (a) Kidney worms of the family Dioctophymatidae, for example, Dioctophyma renale of the genus Dioctophyma spp.; (b) Kidney insects of the family Soboliphymatidae, such as Soboliphyme abei, Soboliphyme baturini of the Soboliphyme spp.
• Trichocephalida (a) Trichinella of the family Trichinellidae, for example, Trichinella spiralis of the Trichinella spp.; (b) Whipworms of the family Trichuridae, such as Capillaria spp., Capillaria annulata, Capillaria contorta, hepatic capillary nematodes ( Capillaria hepatica), Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris spp., Trichuris vulpis, cattle Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis.
• Capillaria spp. Capillaria annulata, Capillaria contorta, hepatic capillary nematodes ( Capillaria hepatica), Capillaria perforans, Capillaria plica, Capillaria suis; Trichuri
• Nematodes of the order Rhabditida Strongyloididae of the family Strongyloididae such as Strongyloides papillosus of the genus Strongyloides spp., cat feces Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti .
• Nematodes of the order Strongylida Hookworms of the family Ancylostomatidae such as Ancylostoma braziliense, Ancylostoma caninum, and Zubini hookworm of the Ancylostoma spp.
• Ancylostoma duodenale Ancylostoma tubaeforme
• Uncinaria stenocephala Uncinaria stenocephala
• Bunostomum spp. Bunostomum phlebotomum, sheep hookworm ( Bunostomum trigonocephalum).
• Nematodes of the order Strongylida (a) Nematodes of the family Angiostrongylidae, for example Aelurostrongylus abstrusus of the genus Aelurostrongylus spp.; Angiostrongylus vasorum, Angiostrongylus cantonesis of the genus Angiostrongylus spp.; (b) Nematodes of the family Crenosomatidae, such as Crenosoma spp., Crenosoma aerophila, Crenosoma vulpis; (c) nematodes of the family Filaroididae, such as Filaroides spp., canine lungworm (Filaroides hirthi), Filaroidesosleri; (d) Lungworms of the family Metastrongylidae, such as Metastrongylus spp., Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus pdendo
• Nematodes of the order Strongylida (a) Nematodes of the family Molineidae, such as Nematodirus filicollis of the genus Nematodirus spp., Nematodirus spa Tigger (Nematodirus spathiger); (b) Nematodes of the family Dictyocauridae, such as Dictyocaulus spp., filamentous lungworm (Dictyocaulus filaria), bovine lungworm (Dictyocaulus viviparus); (c) Nematodes of the family Haemonchidae, such as Haemonchus contortus of the genus Haemonchus spp.; bovine contortus of the genus Mecistocirrus spp.
• Nematodes of the order Strongylida (a) Nematodes of the family Chabertiidae, such as Chabertia ovina of Chabertia spp.; intestinal nodules Oesophagostomum brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, of the genus Oesophagostomum spp.
• Intestinal noduleworm (Oesophagostomum maplestonei), Intestinal noduleworm (pig) (Oesophagostomum quadrispinulatum), Bovine intestinal noduleworm (Oesophagostomum radiatum), Goat intestinal noduleworm (Oesophagostomum venulosum), Intestinal noduleworm (boar) (Oesophagostomum watanabei); (b) nematodes of the Stephanuridae family, such as Stephanurus dentatus of the Stephanurus spp.; (c) Nematodes of the strongyle family (Strongylidae), such as Strongylus spp., Strongylus asini, Strongylus edentatus, Strongylusequinus, Strongyle (Strongylus vulgaris).
• Nematodes of the order Oxyurida Nematodes of the family Oxyuridae, such as Enterobius spp., Enterobius anthropopitheci, Enterobius vermicularis; Oxyuris spp.), the horse pinworm (Oxyuris equi); the rabbit pinworm (Passalurus ambiguus), of the Passalurus spp.
• Nematodes of the order Ascaridida (a) Nematodes of the family Ascaridiidae, such as Ascarididae spp. spp.), chicken roundworm (Ascaridia galli); (b) Nematodes of the family Heterakidae, such as Heterakis spp., Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum; , Heterakis pusilla, Heterakis putaustralis; (c) nematodes of the family Anisakidae, such as Anisakis simplex of the genus Anisakis spp.; (d) Nematodes of the Ascarididae family, such as Ascaris lumbricoides of the Ascaris spp., Ascaris suum; horse roundworms of the Parascaris spp.
• Nematodes of the family Toxocaridae such as Toxocara spp., Toxocara canis, Toxocara leonina, Toxocarasuum, Toxocara vitulorum; ), Toxocara cati.
• Nematodes of the order Spirurida (a) Nematodes of the family Onchocercidae, such as Brugia spp., Brugia malayi, Brugia pahangii (Brugia pahangi), Brugia patei; Dipetalonema spp., Dipetalonema reconditum; Dirofilaria spp., Dirofilaria Filaria oculi; Onchocerca spp.; Cervical threadworm (Onchocerca cervicalis); Onchocerca gibsoni; Pharyngeal threadworm Insect (Onchocerca gutturosa); (b) Nematodes of the Setariidae family, such as Setaria digitata, Setaria equina, Setaria labiatopapillosa, of the Setaria spp.
• Nematodes of the family Filariidae such as Parafilaria multipapillosa of the genus Parafilaria spp.; Stephanofilaria assumum of the genus Stephanofilaria spp. Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.
• Nematodes of the order Spirurida (a) Nematodes of the family Gnathostomatidae, such as Gnathostoma doloresi of the genus Gnathostoma spp.
• Nematodes of the family Habronematidae such as Habronema majus, Habronema microstoma, Habronema muscae of the genus Habronema spp.; Draschia Draschia megastoma of the genus and species (Draschia spp.);
• Nematodes of the family Physalopteridae such as Physaloptera spp., Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera spp.
• Physaloptera felidis Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaloptera rara), Physaloptera sibirica, Physaloptera vulpineus;
• nematodes of the family Gongylonematidae such as Gongylonema pulchrum of the genus Gongylonema spp.
• nematodes of the Spirocercidae family such as Ascarops strongylina of the Ascarops species (Ascaropsspp.)
• Nematodes of the family Thelaziidae such as Thelazia spp., Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Rhodesian eye; worm (Thelazia rh
• the compounds of the present invention can also be applied to pests that have poisonous stingers and venom and cause damage to humans and animals, pests that transmit various pathogens and pathogens, and pests that cause discomfort to humans (toxic pests, sanitary pests, unpleasant pests). etc.) has excellent control effects.
• Pests of the order Hymenoptera wasps of the family Argidae, wasps of the family Cynipidae, wasps of the family Diprionidae, ants of the family Formicidae, wasps of the family Mutillidae, A wasp of the family Vespidae.
• Formulation 1 Hydrating agent 40 parts of the compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely ground to obtain a wettable powder containing 40% of the active ingredient.
• Formulation 3 Granules 5 parts of the compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are mixed uniformly, pulverized finely, and then granulated into particles with a diameter of 0.5 to 1.0 mm. Granules with 5% active ingredient are obtained.
• Formulation 4 Granules 5 parts of the compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate were thoroughly pulverized and mixed, water was added and the mixture was thoroughly kneaded, and then granulated and dried. Granules with 5% active ingredient are obtained.
• Formulation 5 Suspension agent 10 parts of the compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed to obtain a particle size of 3 microns or less. Wet milling to obtain a suspension containing 10% of the active ingredient.
• Formulation 6 Granules 5 parts of the compound of the invention are dissolved in an organic solvent to obtain a solution, the solution is sprayed onto 94 parts of kaolin and 1 part of white carbon, and the solvent is then evaporated under reduced pressure. Granules of this type can be mixed with animal feed.
• Formulation 7 Injection
• 0.1 to 1 part of the compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed, and then sterilized by filtration using a sterilizing filter.
• composition 8 pour-on agent
• a pour-on agent is obtained by uniformly mixing 5 parts of the compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol.
• a spot-on agent is obtained by uniformly mixing 10 to 15 parts of the compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol.
• Formulation 10 Spray
• a spray is obtained by uniformly mixing 1 part of the compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol.
• Step 1 From L-serine to (S)-3- ⁇ 3,5-bis(trifluoromethyl)benzoyl ⁇ oxazolidine-4-carboxylic acid (English name: (S)-3- ⁇ 3,5-bis(trifluoromethyl )benzoyl ⁇ oxazolidine-4-carboxylic acid)
• Step 2 Methyl (S)-3- ⁇ 3,5-bis(trifluoromethyl)benzoyl ⁇ oxazolidine-4-carboxylate (English name: methyl (S)-3- ⁇ 3,5-bis(trifluoromethyl) benzoyl ⁇ oxazolidine-4-carboxylate)
• Step 3 (S)-3- ⁇ 3,5-bis(trifluoromethyl)benzoyl ⁇ oxazolidine-4-carboxamide (English name: (S)-3-(3,5-bis(trifluoromethyl)benzoyl)oxazolidine- (conversion to 4-carboxamide)
• Step 4 (S)-3- ⁇ 3,5-bis(trifluoromethyl)benzoyl ⁇ -N- ⁇ (dimethylamino)methylene ⁇ oxazolidine-4-carboxamide (English name: (S)-3- ⁇ 3, Conversion to 5-bis(trifluoromethyl)benzoyl ⁇ -N- ⁇ (dimethylamino)methylene ⁇ oxazolidine-4-carboxamide)
• Step 5 (R)-6-(5-[3- ⁇ 3,5-bis(trifluoromethyl)benzoyl ⁇ oxazolidin-4-yl]-1H-1,2,4-triazol-1-yl) (conversion to nicotinonitrile)
• Step 1 (R)-3-(t-butoxycarbonyl)thiazolidine-4-carboxylic acid (English name: (R)-3-(tert-butoxycarbonyl)thiazolidine-4-carboxylic acid) to t-butyl (R) Conversion to -4-carbamoylthiazolidine-3-carboxylate (English name: tert-butyl (R)-4-carbamoylthiazolidine-3-carboxylate)
• Step 2 t-butyl (R)-4- ⁇ 1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl ⁇ thiazolidine-3-carboxylate (English name: tert-butyl (R)-4- ⁇ 1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl ⁇ thiazolidine-3-carboxylate)
• the obtained product was purified by silica gel column chromatography to obtain t-butyl (R)-4-(1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl)thiazolidine- 1.75 g of 3-carboxylate was obtained.
• the retention time in liquid chromatography mass spectrometry (LCMS) was 0.69 minutes.
• Step 3 (R)-4- ⁇ 1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl ⁇ thiazolidine dihydrochloride (English name: (R)-4- ⁇ 1- (pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl ⁇ thiazolidine dihydrochloride)
• Step 1 t-butyl (R)-2-carbamoylpyrrolidine-1-carboxylate (English name: tert-butyl (R)-2-carbamoylpyrrolidine-1-carboxylate) to t-butyl (R)-2-[ ⁇ Conversion to (dimethylamino)methylene ⁇ carbamoyl]pyrrolidine-1-carboxylate (English name: tert-butyl(R)-2-[ ⁇ (dimethylamino)methylene ⁇ carbamoyl]pyrrolidine-1-carboxylate)
• Step 2 t-butyl (R)-2- ⁇ 1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl ⁇ pyrrolidine-1-carboxylate (English name: tert-butyl (R)-2- ⁇ 1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl ⁇ pyrrolidine-1-carboxylate)
• Step 3 (R)-2- ⁇ 5-(pyrrolidin-2-yl)-1H-1,2,4-triazol-1-yl ⁇ pyrimidine dihydrochloride (English name: (R)-2- ⁇ 5- (pyrrolidin-2-yl)-1H-1,2,4-triazol-1-yl ⁇ pyrimidine dihydrochloride)
• Step 4 (R)- ⁇ 3,5-bis(trifluoromethyl)phenyl ⁇ [2- ⁇ 1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl ⁇ pyrrolidine -1-yl]methanone (English name: (R)- ⁇ 3,5-bis(trifluoromethyl)phenyl ⁇ [2- ⁇ 1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5- yl ⁇ pyrrolidin-1-yl]methanone)
• Example 5 In the following process, 6-(5-[4- ⁇ 3,5-bis(trifluoromethyl)benzoyl ⁇ morpholin-3-yl)]1H-1,2,4-triazol-1-yl)nicotino Nitrile (English name: 6-(5-[4- ⁇ 3,5-bis(trifluoromethyl)benzoyl ⁇ morpholin-3-yl)]1H-1,2,4-triazol-1-yl)nicotinitrile) was produced.
• Step 1 t-butyl 3-carbamoylmorpholine-4-carboxylate (English name: tert-butyl 3-carbamoylmorpholine-4-carboxylate) to t-butyl 3-[ ⁇ (dimethylamino)methylene ⁇ carbamoyl]morpholine-4- Conversion to carboxylate (English name: tert-butyl 3-[ ⁇ (dimethylamino)methylene ⁇ carbamoyl]morpholine-4-carboxylate)
• Step 2 t-butyl 3- ⁇ 1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl ⁇ morpholine-4-carboxylate (English name: tert-butyl 3 - ⁇ 1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl ⁇ morpholine-4-carboxylate)
• Step 3 6- ⁇ 5-(morpholin-3-yl)-1H-1,2,4-triazol-1-yl ⁇ nicotinonitrile hydrochloride (English name: 6- ⁇ 5-(morpholin-3-yl) )-1H-1,2,4-triazol-1-yl ⁇ nicotinitrile hydrogen chloride)
• Step 4 6-(5-[4- ⁇ 3,5-bis(trifluoromethyl)benzoyl ⁇ morpholin-3-yl)]1H-1,2,4-triazol-1-yl)nicotinonitrile ( English name: Conversion to 6-(5-[4- ⁇ 3,5-bis(trifluoromethyl)benzoyl ⁇ morpholin-3-yl)]1H-1,2,4-triazol-1-yl)nicotinitrile)
• LCMS retention time was determined by the following method.
• Ultra-high-performance high-resolution liquid chromatograph ACQUITY UPLC H-Class: manufactured by Waters
• ACQUITY UPLC photodiode array (PDA) e ⁇ detector manufactured by Waters
• ACQUITYQDa detector positive and negative ion electrospray mode
• UV A Waters CORTECS UPLC C18 column manufactured by Waters, 2.1 x 50 mm, 1.6 ⁇ m
• PDA detection manufactured by Waters
• Insect killing rate (%) (number of dead insects/number of tested insects) x 100
• Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm by mass to obtain a diluted solution (I).
• Emulsion (II) was diluted with water in an amount to give the same dilution ratio as diluted solution (I) to obtain diluted solution (II).
• Corn leaf pieces were immersed in each of diluted solution (I) and diluted solution (II) for 30 seconds. The corn leaf pieces after the soaking treatment were placed in a Petri dish, and five 2nd instar armyworm larvae were released therein. The petri dish was left in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%. Six days after the insects were released, the insects were judged to be alive or dead, and the killing rate was calculated. The test was performed in two replicates.
• Control rate ⁇ 1- (Nt)/(Nc) ⁇ 100
• Nt Number of parasites in the diluted solution (I) treated area
• Nc Number of parasites in the diluted solution (II) treated area
• the heteroaryl compounds of the present invention can be used for pest control, It can be understood that it is a compound that has particularly acaricidal and insecticidal effects. It can also be understood that the compound is effective against parasites that are harmful to humans and animals, such as ectoparasites and endoparasites.

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• 2023
  • 2023-06-13 WO PCT/JP2023/021894 patent/WO2023248871A1/ja not_active Ceased
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