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WO2019022002A1 - Composé 1-hétérodiène et agent de lutte antiparasitaire - Google Patents

Composé 1-hétérodiène et agent de lutte antiparasitaire Download PDF

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WO2019022002A1
WO2019022002A1 PCT/JP2018/027487 JP2018027487W WO2019022002A1 WO 2019022002 A1 WO2019022002 A1 WO 2019022002A1 JP 2018027487 W JP2018027487 W JP 2018027487W WO 2019022002 A1 WO2019022002 A1 WO 2019022002A1
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耕太郎 柴山
寛人 鈴木
岩佐　孝男
隆太郎 清田
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日本曹達株式会社
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    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/382—Heterocyclic compounds having sulfur as a ring hetero atom having six-membered rings, e.g. thioxanthenes
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles 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
    • A61K31/435—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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines 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
    • A61K31/495—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
    • 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
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D411/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/02—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 two hetero rings
    • C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • Q 1 represents a substituted or unsubstituted C6 ⁇ 10 aryl group
  • Q 2 represents a substituted or unsubstituted C1 ⁇ 6 alkyl group, a substituted or unsubstituted C6 ⁇ 10 aryl group
  • R 5 represents a hydrogen atom
  • A represents an oxygen atom or a sulfur atom
  • B represents an oxygen atom or a sulfur atom
  • D represents a substituted or unsubstituted 5- to 10-membered heteroaryl group.
  • E represents an unsubstituted methylene group, a carbonyl group, or an oxygen atom
  • E represents a substituted or unsubstituted benzene ring.
  • Q 1 represents a substituted or unsubstituted C6-10 aryl group.
  • Examples of the “C 6-10 aryl group” in Q 1 include a phenyl group and a naphthyl group. Of these, phenyl is preferred.
  • C1 ⁇ 6 alkyl group in Q 2 are may be linear, may be branched as long as three or more carbon atoms.
  • alkyl group 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, t-butyl group And i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like. Of these, n-pentyl is preferred.
  • C1-6 alkyl group having a substituent Fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trifluoro Ethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1 -C1-6 haloalkyl group such as -trifluoromethylethyl group, perfluoropropan-2-yl group, (perfluorobutyl) methyl group, perfluorohexyl group, perchlorohexyl group, 2,4,6-trichlorohexyl group ;
  • Examples of the “C 6-10 aryl group” in Q 2 include the same as those specifically exemplified in Q 1 .
  • the salt of compound (I) is not particularly limited as long as it is an agronomically acceptable salt.
  • Examples of salts of the compound (I) 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; alkaline earths such as calcium and magnesium Salts of metalloids; salts of transition metals such as iron and copper; and salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine.
  • Hemiptera Brachysera (Archaeorrhyncha)
  • Pentatomidae Of the Pentatomidae (Pentatomidae), for example, of the Nezara species (Nezara spp.), Green-streated bug (Nezara antennata), South- American stink bug (Nezara viridula); , Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, and others, Dolycoris baccarum, Eurydema rugosum, and Bryophytes Halyomorpha halys), P. pipisodorus hybneri, P. japonicus (Plautia crossota), S.
  • the mealybug (Unaspis euonymi), the mealybug (Unaspis yanonensis); and the other mealybugs (Aonidiella aurantii), the mealworm (Comstockaspis perniciosa), the mealworm (Fiorinia theae); );
  • G of the family Aphididae (Phylloxeridae), for example, the grapevine aphid (Viteus vitifolii);
  • H of the family Pseudococcidae, for example, of the genus Planococcus sp.
  • Insect pests of the beetle order (a) For example, tobacco beetles (Lasioderma serricorne) of the family Anobiidae (Anobiidae); (B) of the family Attelabidae, for example, Byctiscus betulae, Rhynchichis heros; (C) of the family Bostrichidae, eg, Lyctus brunneus; (D) of the family Brentidae (Brentidae), for example, Cylas formicarius; (E) of the family Buprestidae (Buprestidae), for example, Agrillus sinuatus; (F) Of the family of Cerambycididae (Cerambycidae), for example, Anodlophora malasiaca, Pinus longicornus (Monochamus alternatus), Pterocarpus longiflorum (Psacothea hilaris), Grape
  • Mite mites Penthaleidae mites, such as, for example, Penthaleus erythrophalus of the genus Pentareus sp. (Penthaleus spp.), And green mites (Penthaleus major).
  • an insecticide / acaricide a nematocide
  • a soil insecticide / acaricide an insecticide, etc. that can be used in combination or in combination with the pest control agent of the present invention are shown below.
  • GABA-agonizing chloride ion channel antagonist acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprol, pyriprole; campechlor, heptachlor, dienochlor.
  • Mitotic proliferation inhibitors and cytostatics (A) ⁇ -tubulin polymerization inhibitor: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate methyl; dietofencarb, zoxamide, etaboxam; (B) cell division inhibitors: penciclone; (C) Delocalization inhibitors of spectrin-like protein: fluopicolide.
  • Signal transduction inhibitors (A) Signal transduction inhibitors: quinoxyfene, proquinazide; (B) MAP-histidine kinase inhibitors in osmotic signaling: fenpicronil, fludioxonil; clozolimate, iprodione, procymidone, vinclozoline.
  • Lipid and cell membrane synthesis inhibitors (A) Phospholipid biosynthesis, methyl transferase inhibitors: Edifenphos, iprovenphos, pyrazophos; (B) lipid peroxides: biphenyl, chloroneb, dichlorane, quindozen, technazen, tolclophos methyl; etordiazole; (C) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb bosecetate, prothiocarb; (D) Microorganisms that disrupt pathogen cell membranes: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain; (E) Agents that disrupt cell membranes: extracts of Goseika Jupte (tea tree).
  • Sterol biosynthesis inhibitor of cell membrane (A) Demethylation inhibitors at position C14 in sterol biosynthesis: Trifolin; pyriphenox, pilisoxazole; phenarimol, flulprimidol, nualimol; imazaryl, imazalil sulfate, oxosconazole, peflazoate, prochloraz, triflumisole , Biniconazole; Azaconazole, biteltanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinonazole, flusilazole, flutriaazole, fluconazole, fluconazole-cis , Hexaconazole, imibenconazole, ipconazole, metcon
  • Ectoparasites infect the body and skin of host animals, particularly warm-blooded animals and fish. More specifically, it infests the back of the host animal, underarms, lower abdomen, inner crotch, etc., and ingests and ingests nutrient sources such as blood and dandruff from the animal. As ectoparasites, ticks, lice, fleas, flies, lice and the like can be mentioned. Specific examples of ectoparasites that can be controlled by the ectoparasite control agent of the present invention are shown below.
  • Psoroptidae mites of the family Psoroptidae (Psoroptidae), such as Psoroptidae
  • the lice (Phthiraptera) of the lice (Anoplura) (a) lice of the family Haematopinidae, such as the lice (Haematopinus asini), the cow lice (Haematopinus eurysternus), the pig lice (Haematopinus suis) of the lice species (Haematopinus spp.); (b) Lice of the family Linognathidae (Linognathidae), for example, the species Linognathus spos. of the species Linognathus spp.
  • Linognathus pedalis (Linognathus pedalis), goat lice (Linognathus stenopsis); such as, for example, Solenopotes spp., Solenopotes capillatus; (2) Bugs of the order Amblycera (biting louse) (a) Hotheads of the family Tanopakidae (Menoponidae), for example, chicken fly flea (Menacanthus stramineus) of the species Genacantha sp.
  • fly fly (Calliphoridae) flies such as the fly fly species (Calliphora), the fly fly (Calliphora lata); for example the fly fly species (Lucilia spp.), the sheep fly fly (Lucilia (Phaenicia) cuprina) Phaenicia) sericata), green leaf fly (Lucilia illustris); such as the spiny fly (Chrysomya hominivorax), chrysomya chloropyga, chrysomya chloromyga, chrysomya veveana (Chrysomya sph.) (f) A fly of the sheep fly family (Oestridae), for example, a rabbit fly species (Cuterebra spp.) of the family of the family Flyfly Subfamily (Cuterebrinae); such as a fly of the genus Bovine fly (Hypoderma spp.); (Hypoderma spp.); (Hypoderma
  • 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 grinding to obtain a 10% suspension of the active ingredient.
  • 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 filter-sterilized with a sterilizing filter.
  • Formulation 9 Spot-on agent 10 to 15 parts of the compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol are uniformly mixed to obtain a spot-on agent.
  • Formulation 10 Spray
  • 10 parts of propylene glycol and 89 parts of isopropanol are uniformly mixed to obtain a spray.
  • the compounds of the numbers shown in Table 4 were tested for efficacy against Hessonia sinensis. Each of the compounds showed an insecticidal rate of 80% or more against the lotus cutlet.
  • Emulsion (I) was diluted with water to a concentration of the compound of the present invention of 125 ppm.
  • the cabbage leaves were immersed in the diluted solution for 30 seconds.
  • the cabbage leaves were air-dried and placed in a petri dish, and five P. moth larvae were released.
  • the petri dish was placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 60%.
  • life and death judgments were made and the insecticidal rate was calculated. The test was performed in duplicate.
  • Test Example 4 Efficacy test against cotton aphid (Aphis gossypii) Cucumber seeds were sown in a 3 inch bowl, and adult cotton aphid was released when 10 days had passed after germination. One day after the helminth, adults were removed, leaving only the 1st instar larvae delivered. The emulsion (I) was diluted with water to obtain a test solution adjusted to a predetermined concentration of the compound of the present invention. The test solution was sprayed on the cucumber. Thereafter, the cucumber was placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 60%. Six days after that, life and death of cotton aphid were examined, and the insecticidal rate was calculated. The test was performed in duplicate.
  • Emulsion (I) was diluted with water to a concentration of 125 ppm of the compound of the present invention. The diluted solution was sprayed on the beans. The beans were placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 65%. Three days after the application, the life and death of adult mite females were examined. The test was performed in duplicate.
  • Test Example 8 Contact Effect Test on Rhipicephalus microplus A DMSO solution of the compound of the present invention was diluted with water to obtain 100 ppm of a test solution. This drug solution was dropped into a container containing 20 larvae of bullfrog tick and incubated in a temperature-controlled room at a temperature of 28 ° C. and a humidity of 80%. Life and death of the larvae were judged 24 hours after the drug solution was dropped. The test was performed in duplicate.
  • Test Example 9 Contact Effect Test on Cat Flea (Ctenocephalides felis)
  • a DMSO solution of the compound of the present invention was diluted with water to obtain 100 ppm of a test solution.
  • This drug solution was dropped onto a filter paper in a container containing 10 adult cat fleas and incubated in a temperature-controlled room at a temperature of 28 ° C. and a humidity of 80%. Life and death of adults were determined 24 hours after the drug solution was dropped. The test was performed in duplicate.

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Abstract

L'invention concerne un composé représenté par la formule (I) ou un sel de celui-ci. (Dans la formule (I), Q1 représente un groupe aryle en C6-10 (non)substitué ; Q2 représente un groupe alkyle en C1-6 (non)substitué, un groupe aryle en C6-10 (non)substitué, ou un groupe hétéroaryle (non)substitué ayant de cinq à dix chaînons ; R1 représente un atome d'hydrogène ; A représente un atome d'oxygène ou de soufre ; B représente un atome d'oxygène ou un atome de soufre ; D représente un groupe méthylène (non)substitué, un groupe carbonyle ou un atome d'oxygène ; et E représente un cycle benzénique (non)substitué.)
PCT/JP2018/027487 2017-07-26 2018-07-23 Composé 1-hétérodiène et agent de lutte antiparasitaire WO2019022002A1 (fr)

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