WO2019208598A1 - Composé de pyrimidine et composition de lutte contre les arthropodes nuisibles le contenant - Google Patents

Composé de pyrimidine et composition de lutte contre les arthropodes nuisibles le contenant Download PDF

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Publication number
WO2019208598A1
WO2019208598A1 PCT/JP2019/017320 JP2019017320W WO2019208598A1 WO 2019208598 A1 WO2019208598 A1 WO 2019208598A1 JP 2019017320 W JP2019017320 W JP 2019017320W WO 2019208598 A1 WO2019208598 A1 WO 2019208598A1
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Prior art keywords
compound
methyl
virus
present
group
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PCT/JP2019/017320
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English (en)
Japanese (ja)
Inventor
康 片桐
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住友化学株式会社
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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
    • A01N43/48—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
    • 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
    • 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
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom

Definitions

  • the present invention relates to a pyrimidine compound and a harmful arthropod control composition containing the same.
  • Patent Document 1 describes that certain compounds have a pest control effect.
  • An object of the present invention is to provide a compound having an excellent control effect against harmful arthropods.
  • the present invention is as follows. [1] Formula (I) [Wherein, R represents a methyl group or an ethyl group. ] (Hereinafter referred to as the present compound). [2] A harmful arthropod control composition comprising the compound according to [1] and an inert carrier. [3] A method for controlling harmful arthropods, which comprises applying an effective amount of the compound according to [1] to harmful arthropods or habitats of harmful arthropods.
  • a composition comprising one or more components selected from the group consisting of group (a) and group (b), and the compound according to [1]: Group (a): a group consisting of an insecticidal active ingredient, an acaricidal active ingredient and a nematicidal active ingredient; Group (b): bactericidal active ingredient.
  • Group (a) a group consisting of an insecticidal active ingredient, an acaricidal active ingredient and a nematicidal active ingredient
  • Group (b) bactericidal active ingredient.
  • a method for controlling harmful arthropods which comprises applying an effective amount of the composition according to [4] to harmful arthropods or habitats of harmful arthropods.
  • a seed or vegetative organ holding an effective amount of the compound according to [1] or the effective amount of the composition according to [4].
  • harmful arthropods can be controlled.
  • the compound of the present invention is mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid or benzoic acid, thereby adding an acid addition salt such as hydrochloride, sulfate, nitrate, phosphate, acetate or benzoate. May form.
  • an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid or benzoic acid, thereby adding an acid addition salt such as hydrochloride, sulfate, nitrate, phosphate, acetate or benzoate. May form.
  • the compounds of the present invention include any active isomers and mixtures thereof.
  • the isomer is represented by the formula (IA) in which the relative configuration of the substituent at the 1-position and the substituent at the 4-position of the cyclohexane ring is cis-coordinate.
  • a compound of formula (IB) in which the relative configuration is trans coordination The compound shown by these is mentioned.
  • the relative configuration of the substituent at the 1-position and the substituent at the 4-position of the cyclohexane ring is preferably cis-coordinate.
  • Examples of the compound of the present invention include the following compounds.
  • a compound in which the relative configuration of the substituent at the 1-position and the substituent at the 4-position of the cyclohexane ring is cis-coordinate.
  • compounds wherein R is a methyl group hereinafter referred to as the present compound 1.
  • a compound wherein R is an ethyl group hereinafter referred to as the present compound 2.
  • compounds wherein R is a methyl group hereinafter referred to as the present compound 3).
  • the compound of the present invention comprises the following group (a), group (b), group (c), group (d), group (e), group (f), group (g), and group (h).
  • One or more selected components can be used in combination or in combination.
  • the mixed use or combination means that the compound of the present invention and the present component are used simultaneously, separately or at intervals.
  • the compound of the present invention and this component may be contained in separate preparations or may be contained in one preparation.
  • One aspect of the present invention is a composition (hereinafter referred to as composition A) containing one or more components selected from the group consisting of group (a) and group (b) and the compound of the present invention.
  • Group (a) includes acetylcholinesterase inhibitors (eg carbamate insecticides, organophosphorus insecticides), GABAergic chloride channel antagonists (eg phenylpyrazole insecticides), sodium channel modulators (eg pyrethroid insecticides) ), Nicotinic acetylcholine receptor antagonist modulators (eg neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamatergic chloride channel allosteric modulators (eg macrolide insecticides), juvenile hormone mimics , Multi-site inhibitor, chordal organ TRPV channel modulator, mite growth inhibitor, mitochondrial ATP biosynthesis enzyme inhibitor, oxidative phosphorylation uncoupler, nicotinic acetylcholine receptor Channel blockers (eg, nereistoxin insecticides), chitin synthesis inhibitors, molting inhibitors, ecdysone receptor agonists, oc
  • Group (b) includes nucleic acid synthesis inhibitors (eg, phenylamide fungicides, acylamino acid fungicides), cell division and cytoskeleton inhibitors (eg, MBC fungicides), respiratory inhibitors (eg, QoI fungicides) , QiI fungicides), amino acid synthesis and protein synthesis inhibitors (eg, anilinopyridine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (eg, triazole-based DMI) Bactericides), cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-acting contact active bactericides, microbial bactericides, and other bactericidal active ingredients. These are described in the classification based on the mechanism of action of FRAC.
  • nucleic acid synthesis inhibitors eg, phenylamide fungicides, acylamino acid fungicides
  • Group (c) is a group of plant growth regulating components (including mycorrhizal fungi and rhizobia).
  • Group (d) is a group of chemical damage reducing components.
  • Group (e) is a group of synergists.
  • Group (f) is a group of repellent components comprising bird repellent components, insect repellent components, and animal repellent components.
  • Group (g) is a group of mollusc component.
  • Group (h) is a group of insect pheromones.
  • alanycarb + SX means a combination of alanycarb and SX.
  • the abbreviation SX means any one of the compounds 1 to 6 of the present invention.
  • all of the components described below are known components and can be obtained from commercially available preparations or produced by known methods. If this component is a microorganism, it can also be obtained from a fungus depository.
  • the numbers in parentheses represent CAS RN (registered trademark).
  • Amyloliquefaciens FZB24 + SX Bacillus subtilis Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin J82 + SX, Burkholderia cepacia type Wisconsin M54 + SX, Octo Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans CGMCC8325 + SX, Coniothyrium minitans CON / M / 91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp.
  • the ratio of the compound of the present invention to this component is not particularly limited, but is 1000: 1 to 1: 1000, 500: 1 to 1: 500, 100: 1 in weight ratio (the compound of the present invention: this component). ⁇ 1: 100, 50: 1, 20: 1, 10: 1, 9: 1, 8: 1, 7: 1, 6: 1, 5: 1, 4: 1, 3: 1, 2: 1, 1 : 1, 1: 2, 1: 3, 1: 4, 1: 5, 1: 6, 1: 7, 1: 8, 1: 9, 1:10, 1:20, 1:50, etc. .
  • the compound of the present invention is effective against harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful molluscs.
  • harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful molluscs.
  • harmful arthropods, harmful nematodes, and harmful molluscs include the following.
  • Hemiptera Japanese green planthopper (Laodelphax striatellus), Japanese brown planthopper (Nilaparvata lugens), white-tailed planthopper (Sogatella furcifera), corn planter (Peregrinus maidis), yellow-spotted fish (Javesella pellucida), Perukinsiori Leafhopper (Delphacidae); Nephotettixepscincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Eaca Corn leaf hopper (Dalbulus maidis), leafhopper (Cicadellidae) such as Cofanaofspectra; Mahanarva posticata, Mahanarva fimbriolata, etc.
  • Bean aphids (Aphis fabae), soybean aphids (Aphis glycines), cotton aphids (Aphis gossypii), European apple aphids (Aphis pomi), snowy aphids (Aphis spiraecola), peach aphids (Myzus persicae), barley aphids helichrysi), radish aphids (Brevicoryne brassicae), Rosy apple aphid (Dysaphis plantaginea), black pea aphids (Lipaphis erysimi), tulip beetles (Macrosiphum euphorbiae), potato beetles Barley beetle (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus aphid (Toxoptera citricida), peach beetle (Hy
  • Troatomae Such as Giant Cicada (Quesada gigas); Cicadidae; Brazilian turtle (Triatoma infestans); Venezuelan turtle (Rhodonius prolixus) and other genus Reduviidae; Triatoma spp.).
  • Lepidoptera Green moth (Chilo suppressalis), Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Itteno moth (Scirpophaga incertulas), Rupela albina cis martialis cis Casino maiga (Marasmia exigua), cotton moth (Notarcha derogata), yellow corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), yellow-tailed moth (Hellula undalis), Monkikuro moth terrel Caseworms (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc.
  • Noctuidae Diantha (Grapholita dimorpha), Leguminivora ⁇ glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes nanima, Monakiki Archips fuscocupreanus), Cydia ⁇ ⁇ pomonella, Tetramoera schistaceana, Bean Shoot Borer (Epinotia aporema), Citrus fruit borer (Ecdytolopha aurantiana), etc.
  • Grapillariidae such as Phyllonorycter ⁇ ringoniella; Carposinidae such as Carposina sasakii; Coffee Leaf miner (Leucoptera coffeella), Lyonetiapella Lymantiidae; Lymantriidae such as Lymantria dispar, Euproctis spp. Such as Euproctis spp.
  • Lymantriidae Plutellidae (Plutellidae); American mosquitoes (Anarsia lineatella), Japanese moth (Helcystogramma triannulella), Cotton moth (Pectinophora gossypiella), Potato moth (Phthorimaea operculella), American horridae (Cu) Hi Arctiidae; Castiidae such as Giant Sugarcane borer (Telchin licus); Boletinaceae such as Cossus insularis; Cossus insularis; Limacodidae, such as Parasa lepida; Staphymopodidae, such as Stahmopoda persistssa; Sphingidae, such as Acherontia lachesis; hector), Sesiidae such as Synanthedon tenuis; Parsaraceae (Parnara guttata); He
  • Thysanoptera Citrus thrips (Frankliniella occidentalis), Thrips palmi, Scirtothrips dorsalis, Thrips Thripidae such as Echinothrips americanus; Thripidae such as Haplothrips aculeatus.
  • Diptera Anthomyiidae such as Dela platura, Delia antiqua, Pegomya cunicularia; Udidiidae such as sugar beet root mygot Agromyza oryzae, tomato leaffly (Liriomyza sativae), beetle leaflet (Liriomyza trifolii), leafhopper (Chromatomyia horticola), etc.
  • Bactrocera cucurbitae citrus fruit fly (Bactrocera ⁇ ⁇ dorsalis), nasal fly (Bactrocera ⁇ latifrons), olive fruit fly (Bactrocera oleae), quinceland fruit fly (Bactrocera tryoni), Ceratitis golet pomonella, Rhacochlaena japonica, etc.
  • Coleoptera Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm (Diabrotica virgifera zeae), Banded cub amber beetle balteata), Cucurbit Beetle (Diabrotica speciosa), Bean Leaf Beetle (Cerotoma trifurcata), Bark beetle beetle (Oulema melanopus), Root beetle (Aulacophora femoralis), Phyllotreta striolata a p flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado beetle (Leptinotarsa decemlineata), rice beetle (Oulema oryzae),
  • Orthoptera Iron grasshopper (Locusta migratoria),ixie grasshopper (Dociostaurus maroccanus), Australian flying grasshopper (Chortoicetes terminifera), Red-footed grasshopper (Nomadacris septemfasciata, Brown Locust (Locustana Pardal), Brown Locust (Locustana pardal) Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoula femurwing) ), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Cobainago (Oxya yezoensis), Species (Oxya japonica), Thai winged chinook (Patanga
  • Hymenoptera Tenthedinidae, such as Athalia rosae, Athalia japonica; Tenthredinidae, Solenopsis geminata, and other genus Toppisari (Solenopsis geminata) leaf-cutting ant (Atta capiguara) and other species of genus Atta spp., genus Acromyrmex spp., scorpionary (Paraponera clavata), rugliari (Ochetellus glaber), common ants (Monomorium pileonis), Argentina ), Black ants (Formica fusca japonica), red ants (Pristomyrmex punctutus), giant ants (Pheidole noda), crested ants (Pheidole megacephala), black ants (Camponotus japonicus), red-tailed ants (Camponotus Shu (Pogonomyrmex occidentalis) Pogonomyr
  • Cockroach (Blattodea): German cockroach (Blattellidae) such as Blattella germanica; Black cockroach (Periplaneta fuliginosa), Greater cockroach (Periplaneta americana), Greater cockroach (Periplaneta brunnea), ali (Blattidae); Yamato termite (Reticulitermes speratus), house termite (Coptotermes formosanus), American ant termite (Incisitermes ⁇ minor), daiko termite (Cryptotermes domesticus), taiwan termite (Odontotermes N ant hunter) Glyptotermes satsumensis), Glyptotermes nakajimai, Caterpillars (Glyptotermes fuscus), Termites (Hodotermopsis sjostedti), Coptotermes guangzhouensis , Amami Termites (Reticulitermes amamianus), Miya
  • Fleas Pulex genus such as human flea (Pulex irritans), Ctenocephalides genus such as cat flea (Ctenocephalides canis), Xenopsylla genus Xenopsyllaung such as Xenopsylla cheopis, Tunga genus, Echidnophaga genus such as chicken flea (Echidnophaga gallinacea), and Nosopsyllus genus such as European rat minnow (Nosopsyllus fasciatus).
  • Pulex genus such as human flea (Pulex irritans), Ctenocephalides genus such as cat flea (Ctenocephalides canis), Xenopsylla genus Xenopsyllaung such as Xenopsylla cheopis, Tunga genus, Echidnophaga genus such as chicken flea (Echidnophaga gallinacea), and Nosops
  • Psocodae genus Pediculus such as head lice (Pediculus humanus capitis); genus Phtirus such as pheasant lice (Pthirus pubis); Damalinia genus such as Damalinia bovis; Bovine white lice (Linognathus vituli), sheep trunk parasitic lice (Linognathus ovillus) genus Linognathus genus; Menopon genus; Trimenopon spp .; Trinoton spp .; Trichodectes genus such as dog lice (Trichodectes canis); Felicola genus such as cat lice (Felicola subrostratus); Men, such as the great wolf (Menacanthus stramineus) Acanthus; Werneckiella spp .; Lepikentron spp .; Liscelis subfuscas, Liposcelis bostrychophilus, Liposcelis simulans, Liposcelis
  • Thysanura Lepismatidae such as Ctenoepisma villosa, Lepisma saccharina.
  • Nite spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), honey spider mite (Tetranychus evansi), citrus spider mite (Panonychus citri), apple spider mite (Panonychus ulmi), Ony s genus (Opp.
  • Citrus mite (Aculops pelekassi), Ryu citrus rust mite (Phyllocoptruta citri), tomato rust mite (Aculops lycopersici), green rust mite (Calacarus carinatus), green moth mite (Acaphylla therio physis), tick (Eca Aculus convincedendali), Aceria ⁇ diospyri, Aceria tosichella, Sheevtchenkella sp., Etc., Eriophyidae; (Tenuipalpidae) such as (Brevipalpus phoenicis); Tuckerellidae; Ixodidae, for example, Haemaphysalis longicornis, Haemaphysalis flavs, tick Haemaphys American dock ticks (Dermacentor variabilis), Dermacentor taiwanicus, Dermacentor andersoni, etc.
  • Ornithodorus genus such as Ornithodorus turicata, Psoroptes ovis, Psoroptes genus Psoroptes cati), the genus Notoedres, such as the mud shrimp mite (Notoedres muris), the genus Sarcoptes, such as Sarcoptes scabiei, the genus Otodectes, such as the octodectes cynotis, and the genus Listrophorus girobus, etc.
  • Ornithodorus genus such as Ornithodorus turicata, Psoroptes ovis, Psoroptes genus Psoroptes cati
  • the genus Notoedres such as the mud shrimp mite (Notoedres muris)
  • the genus Sarcoptes such as Sarcoptes scabiei
  • the genus Otodectes such as the octode
  • Hymenoptera (Chorioptes spp.), Hypodectes spp., Pterolichus spp., Cytodites ⁇ spp., Laminosioptes spp., Dermanyssus gallinae, etc. Torisashi Ornithonyssus sylviarum, Ornithonyssus bacoti, etc., Varroa jacobsoni, Varroa, Cattle ticks (Ornitrocheyletia spp.), Inodex mite (Demodex canis), Feline mite (Demodex cati) and other Demodex genera, Myobia spp. (Trombicula pallida), Trombiculaascutellaris, etc.
  • Araneae Eutrichuridae such as Cheracanthium japonicum; Theridiidae such as Latrodectus hasseltii.
  • Polydesmida Paradoxosomatidae such as Oxidus gracilis and Nedyopus tambanus.
  • Isopoda Armadillidiidae, such as Armadillidium vulgare.
  • Chiropoda Scutigeridae, such as Thereuonema hilgendorfi; Scolopendridae, such as Scolopendra subspinipes;
  • Gastropoda Limax marginatus, Limax flavus, and other scallops (Limacidae); Ampullariidae; Austropepleaeollula, etc.
  • Aphelenchoididae such as Aphelenchoides besseyi; Pratylenchulus coffeae, Pratylenchus brachyurus, Pratilenchus simulis Pratylenenchidae (Pratylenchidae); Java root-knot nematode (Meloidogyne javanica); Heteroderidae such as Cyst nematode (Globodera pallida); Hoplolymidae (Hoplolaimidae) such as Rotilenchulus reniformis; Strawberry nematode (Nothotylenchus acris) Anguinidae such as Ditylenchus dipsaci; Tylenchulidae such as Tylenchulus semipenetrans; Longidoride such as Xiphinema index; Parasitaphelenchidae, such as pine wood nematode (Bursaphele
  • the compounds of the present invention are harmful arthropods such as harmful insects, harmful mites, harmful molluscs, and the like that have reduced sensitivity to insecticides, acaricides, molluscicides and nematicides, or have developed resistance. It can also be used against harmful nematodes.
  • the compound of the present invention can also be used to protect plants from plant diseases caused by insect-borne viruses or insect-borne bacteria.
  • insect-borne viruses examples include the following.
  • insect-borne bacteria examples include the following.
  • Rice yellow dwarf phytoplasma (Candidatus Phytoplasma oryzae), Candidatus Phytoplasma asteris, Maize bushy stunt phytoplasma, citrus greening fungus Asian type (Candidatus Liberbacter ⁇ asiaticus), citrus greening fungus African type (Candidatus cricket) Type (Candidatus Liberbacter americanus).
  • the harmful arthropod control composition of the present invention contains the compound or composition A of the present invention and an inert carrier.
  • the arthropod pest control composition of the present invention is usually prepared by mixing the compound of the present invention or the composition A with an inert carrier such as a solid carrier, liquid carrier, gaseous carrier, etc.
  • an inert carrier such as a solid carrier, liquid carrier, gaseous carrier, etc.
  • the harmful arthropod control composition of the present invention usually contains 0.0001 to 95% by weight of the compound or composition A of the present invention.
  • solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), dry silica, wet silica, talc, ceramic, and other inorganic minerals (sericite, quartz, Sulfur, activated carbon, calcium carbonate, etc.), fine powders and granules of chemical fertilizers (ammonium sulfate, phosphoric acid, ammonium nitrate, urea, ammonium chloride, etc.), etc., and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate) Polyester resins such as nylon-6, nylon-11, nylon-66, polyamide resin, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer, etc.).
  • liquid carrier examples include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), n
  • gaseous carrier examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.
  • surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.
  • adjuvants for preparation include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), acidic isopropyl phosphate, 2,6-di-tert-butyl-4-methylphenol, BHA (2-tert-butyl-4-methoxyphenol) And a mixture of 3-tert-butyl-4-methoxyphenol).
  • fixing agents such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), acidic isopropyl
  • the base material of the resin preparation examples include vinyl chloride polymers, polyurethanes, etc., and these base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.), adipic acid esters as necessary. Further, a plasticizer such as stearic acid may be added.
  • the resin formulation is obtained by kneading the compound in the base material using a normal kneading apparatus, and then molding by injection molding, extrusion molding, press molding, etc., and if necessary, through further steps such as molding, cutting, It can be processed into resin preparations such as plates, films, tapes, nets, and strings.
  • These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, attracting strings, or gardening supports.
  • Examples of the base material of the poison bait include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and further, if necessary, preservation of antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, dehydroacetic acid and the like
  • Ingredients, anti-fouling preventives for children and pets such as pepper powder, cheese flavoring, onion flavoring, pest-attracting flavoring such as peanut oil, and the like are added.
  • the method for controlling harmful arthropods according to the present invention comprises an effective amount of the compound or composition A of the present invention directly on the harmful arthropods and / or habitats of harmful arthropods (plants, soil, households, animals). Etc.). It can also be processed into seeds.
  • Examples of the method for controlling harmful arthropods of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, smoke treatment, water surface treatment and seed treatment.
  • examples of plants include whole plants, foliage, flowers, ears, fruits, trunks, branches, crowns, seeds, vegetative organs and seedlings.
  • Nutritional reproductive organ means plant roots, stems, leaves, etc. that have the ability to grow when their parts are separated from the body and placed in the soil.
  • vegetative reproductive organs include tuberous roots, creeping roots, bulbs, corms or solid bulbs, tubers, rhizomes, and stolons. , Rhizophore, cane-cuttings, propagule and vine-cutting.
  • a toothpick is sometimes called a runner, and a basket is also called a pearl bud, and is divided into a granule (broad bud) and a scale bud (bulbil).
  • the vine means shoots (a general term for leaves and stems, shoot) such as sweet potatoes and yams.
  • a bulb, a bulb, a tuber, a rhizome, a stem fragment, a root bearing body or a tuberous root is collectively called a bulb.
  • Potato cultivation begins with planting tubers in the soil, but the tubers used are commonly referred to as seed pods.
  • the seed or vegetative reproductive organ holding the present compound or composition A in the present invention means a state where the present compound or composition A is attached to the surface of the seed or vegetative reproductive organ. .
  • this invention compound or composition A adhering to the surface may osmose
  • composition A is attached to the surface of seeds or vegetative organs, a plurality of single active ingredient layers may be overlapped, or a single layer in which a plurality of active ingredients are mixed is formed. Alternatively, a single active ingredient layer and a plurality of active ingredient layers may overlap, or a plurality of active ingredient layers may overlap.
  • the seed or vegetative organ used for seed treatment may be used as it is, and materials other than the present compound or composition A may be attached before and after the present compound or composition A is treated. .
  • Examples of the seed treatment include a method in which a suspension of the compound or composition A of the present invention is atomized and sprayed on the seed surface or the surface of the vegetative reproductive organ, and the compound or composition A of the present invention is applied to the seed or the vegetative reproductive organ.
  • a method of immersing seeds or vegetative reproductive organs in a solution of the compound or composition A of the present invention for a certain period of time, coating seeds or vegetative reproductive organs with a carrier (film, pellet, etc.) containing the compound or composition A of the present invention The method of doing is mentioned.
  • the application amount is usually 1 to 10,000 g as the amount of the compound of the present invention per 10,000 m 2 .
  • the amount of the compound of the present invention is usually applied in the range of 0.001 to 100 g per 1 kg of seeds.
  • the harmful arthropod control composition of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually applied after diluting with water so that the active ingredient concentration is 0.01 to 10,000 ppm.
  • the granules, powders, etc. are usually applied as they are.
  • These preparations and water dilutions of these preparations may be sprayed directly onto harmful arthropods or plants such as crops to be protected from harmful arthropods, and also control pests that inhabit cultivated soil Therefore, the soil may be treated.
  • it can be treated by methods such as wrapping a resin preparation processed into a sheet or string around the crop, stretching it around the crop, or laying it on the stock soil.
  • the application amount is the amount of the compound of the present invention per 1 m 2 of treatment area when treated on the surface.
  • the amount of the compound of the present invention per 1 m 3 of treatment space is usually 0.001 to 500 mg when treated in a space.
  • the harmful arthropod control composition of the present invention is formulated into an emulsion, a wettable powder, a flowable, etc., it is usually diluted with water so that the active ingredient concentration is 0.01 to 10,000 ppm. Apply oil, aerosol, smoke, poison bait, etc. as they are.
  • the harmful arthropod control composition of the present invention is used for controlling ectoparasites of domestic animals such as cattle, horses, pigs, sheep, goats and chickens, and small animals such as dogs, cats, rats and mice, veterinary It can be used for animals by known methods.
  • veterinary can be used for animals by known methods.
  • systemic suppression for the purpose of systemic suppression, for example, administration by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is intended for non-systemic suppression.
  • an oil agent or an aqueous liquid is sprayed, a pour-on treatment or a spot-on treatment is performed, the animal is washed with a shampoo preparation, or a resin preparation is attached to the animal with a collar or ear tag.
  • the amount of the compound of the present invention is usually in the range of 0.1 to 1000 mg per kg of animal body weight.
  • the compound or composition A of the present invention can be used as a control agent for harmful arthropods in agricultural land such as fields, paddy fields, lawns, orchards.
  • the compound of the present invention can control harmful arthropods such as cultivated land in cultivated lands where the following plants are cultivated.
  • the above plants include plants that can be produced by natural mating, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops.
  • genetically modified crops include HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactic acid synthase) inhibitors such as imazetapyr and thifensulfuron methyl, EPSP (5 -Plants that have been given tolerance to herbicides such as enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or dicamba Plants capable of synthesizing selective toxins known in the genus Bacillus such as Bacillus thuringiensis; gene fragments that partially match endogenous genes derived from harmful insects, etc. It is synthesized by inducing gene silencing (RNAi
  • 4,5-dichloro-6-ethylpyrimidine, cis-4-methylcyclohexane-1-amine and cis-4-ethylcyclohexane-1-amine are commercially available compounds.
  • a part represents a weight part.
  • Formulation Example 1 10 parts of any one of the compounds SX of the present invention are mixed with a mixture of 35 parts of xylene and 35 parts of DMF, and 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added and mixed. A formulation is obtained.
  • Formulation Example 2 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of wet silica and 54 parts of diatomaceous earth are mixed, and 20 parts of any one of the compounds SX of the present invention are added and mixed to obtain a preparation.
  • Formulation Example 3 1 part of wet silica, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are mixed with 2 parts of any one of the compounds SX of the present invention. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated with a granulator, and dried by ventilation to obtain a preparation.
  • Formulation Example 4 1 part of any one of the compounds SX of the present invention is mixed with an appropriate amount of acetone, and 5 parts of wet silica, 0.3 part of isopropyl acid phosphate and 93.7 parts of kaolin clay are added, and the mixture is sufficiently stirred and mixed. Acetone is removed by evaporation to obtain a preparation.
  • Formulation Example 5 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and wet silica (weight ratio 1: 1), 20 parts of any one of the compounds SX of the present invention, and 45 parts of water are sufficiently mixed to obtain a preparation. .
  • Formulation Example 6 0.1 part of any one of the compounds SX of the present invention is mixed with a mixture of 5 parts of xylene and 5 parts of trichloroethane, and this is mixed with 89.9 parts of kerosene to obtain a preparation.
  • Formulation Example 7 10 mg of any one of the compounds SX of the present invention is mixed with 0.5 mL of acetone, and this solution is added dropwise to 5 g of animal solid feed powder (bred breeding solid feed powder CE-2, Nippon Claire Co., Ltd.), Mix evenly. The acetone is then evaporated to dryness to obtain a poisonous bait.
  • animal solid feed powder termed breeding solid feed powder CE-2, Nippon Claire Co., Ltd.
  • Formulation Example 8 0.1 part of any one of the compounds SX of the present invention and 49.9 parts of neothiozole (manufactured by Chuo Kasei Co., Ltd.) are placed in an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are filled and shaken. And an oil aerosol is obtained by mounting the actuator.
  • Formulation Example 9 0.6 part of any one of the compounds SX of the present invention, 0.01 part of 2,6-di-tert-butyl-4-methylphenol, 5 parts of xylene, 3.39 parts of kerosene and 1 part of rhodol (registered trademark) )
  • a mixture of MO-60 and 50 parts of distilled water are filled into an aerosol container, a valve is attached, and then 40 parts of LPG is filled through the valve to obtain an aqueous aerosol.
  • Formulation Example 10 0.1 g of any one of the compounds SX of the present invention is mixed with 2 mL of propylene glycol and impregnated into a ceramic plate having a size of 4.0 cm ⁇ 4.0 cm and a thickness of 1.2 cm to obtain a heating smoke.
  • Formulation Example 11 5 parts of any one of the compounds SX of the present invention and 95 parts of an ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate to the total weight of the copolymer: 10% by weight) are melt-kneaded, and the resulting kneading The product is extruded from an extrusion molding machine to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.
  • Formulation Example 12 5 parts of any one of the compounds SX of the present invention and 95 parts of a soft vinyl chloride resin are melt-kneaded, and the obtained kneaded product is extruded from an extrusion molding machine to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.
  • Formulation Example 13 100 mg of any one of the compounds SX of the present invention, 68.75 mg of lactose, 237.5 mg of corn starch, 43.75 mg of microcrystalline cellulose, 18.75 mg of polyvinylpyrrolidone, 28.75 mg of sodium carboxymethyl starch, and magnesium stearate 2. 5 mg is mixed and the resulting mixture is compressed to an appropriate size to obtain tablets.
  • Formulation Example 14 One of the compounds SX of the present invention, 25 mg, lactose 60 mg, corn starch 25 mg, carmellose calcium 6 mg, and 5% hydroxypropylmethylcellulose are mixed in an appropriate amount, and the resulting mixture is filled into a hard shell gelatin capsule or hydroxypropylmethylcellulose capsule And a capsule is obtained.
  • Formulation Example 15 Any one of the present compounds SX 100 mg, fumaric acid 500 mg, sodium chloride 2000 mg, methylparaben 150 mg, propylparaben 50 mg, granule sugar 25000 mg, sorbitol (70% solution) 13000 mg, Veegum (registered trademark) K100 mg, flavor 35 mg, and coloring Distilled water is added to 500 mg of the preparation so that the final volume becomes 100 mL, and mixed to obtain a suspension for oral administration.
  • Distilled water is added to 500 mg of the preparation so that the final volume becomes 100 mL, and mixed to obtain a suspension for oral administration.
  • Formulation Example 16 5 parts of any one of the compounds SX of the present invention are mixed with 5 parts of an emulsifier, 3 parts of benzyl alcohol, and 30 parts of propylene glycol, and the phosphate is adjusted so that the pH of this solution is 6.0 to 6.5. After adding a buffer solution, water is added as the balance to obtain a solution for oral administration.
  • Formulation Example 17 5 parts of aluminum distearate is added to 57 parts of fractionated coconut oil and 3 parts of polysorbate 85 and dispersed by heating. This is cooled to room temperature and 25 parts of saccharin is dispersed in the oily vehicle. To this, 10 parts of any one of the compounds SX of the present invention are allocated to obtain a paste preparation for oral administration.
  • Formulation Example 18 5 parts of any one of the compounds SX of the present invention are mixed with 95 parts of limestone powder to obtain granules for oral administration using a wet granulation method.
  • Formulation Example 19 5 parts of any one of the compounds SX of the present invention are mixed with 80 parts of diethylene glycol monoethyl ether, and 15 parts of propylene carbonate is mixed therewith to obtain a spot-on solution.
  • Formulation Example 20 10 parts of any one of the compounds SX of the present invention are mixed with 70 parts of diethylene glycol monoethyl ether, and 20 parts of 2-octyldodecanol is mixed with this to obtain a pour-on solution.
  • Formulation Example 21 0.1 part of any one of the compounds SX of the present invention, 40 parts of sodium polyoxyethylene lauryl ether sulfate (25% aqueous solution), 5 parts of amidopropyl betaine laurate, 5 parts of coconut oil fatty acid ethanolamide, carboxyvinyl polymer Add 5 parts and 49.4 parts of purified water and mix well to obtain a shampoo.
  • Formulation Example 22 0.15 part of any one of the compounds SX of the present invention, 95 parts of animal feed, and 4.85 parts of a mixture comprising calcium hydrogen phosphate, diatomaceous earth, Aerosil (registered trademark), and carbonate (or chalk) are sufficiently stirred. Mix to obtain animal feed premix.
  • Formulation Example 23 7.2 g of any one of the compounds SX of the present invention and 92.8 g of Phosco® S-55 are mixed at 100 ° C., poured into a suppository form, cooled and solidified to obtain a suppository.
  • test examples the efficacy of the compound of the present invention against harmful arthropods is shown by test examples.
  • the test was performed at 25 ° C.
  • Test method 1 A test compound is prepared in accordance with the method described in Formulation Example 5, and water containing 0.03% by volume of Cyndine (registered trademark) is added thereto to prepare a diluted solution containing the test compound at a predetermined concentration. Approximately 30 cotton aphids (all stages) are inoculated into Cucuis sativus seedlings (second true leaf development stage) planted in a container. After 1 day, the diluted solution is sprayed on the seedlings at a rate of 10 mL / seedling. After 5 days, the number of live insects is examined, and the control value is obtained by the following formula.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Tai Number of live insects at the time of survey in the treated group It means a group that operates in the same manner as the treatment group except that the test compound is not used.
  • Test Example 1-1 As a result of testing according to Test Method 1 using the following present compound as a test compound at a predetermined concentration of 500 ppm, all of the following present compounds exhibited a control value of 90% or more.
  • Test Example 1-2 As a result of performing the test according to Test Method 1 using the following present compound as a test compound at a predetermined concentration of 200 ppm, all of the following present compounds exhibited a control value of 90% or more.
  • Test method 2 A test compound is prepared in accordance with the method described in Formulation Example 5, and water containing 0.03% by volume of Cyndine (registered trademark) is added thereto to prepare a diluted solution containing the test compound at a predetermined concentration.
  • Test example 2 As a result of testing according to Test Method 2 using the following present compound as a test compound at a predetermined concentration of 500 ppm, the following present compound showed a mortality rate of 100%.
  • Compound of the present invention 2
  • Test example 3 As a result of testing according to Test Method 3 using the following present compound as a test compound at a predetermined concentration of 500 ppm, all of the following present compounds showed a mortality rate of 80% or more.
  • Test example 4 As a result of testing according to Test Method 4 using the following present compound as a test compound at a predetermined concentration of 500 ppm, all of the following present compounds showed a mortality rate of 90% or more.
  • Test method 5 A test compound is prepared in accordance with the method described in Formulation Example 5, and water containing 0.03% by volume of Cyndine (registered trademark) is added thereto to prepare a diluted solution containing the test compound at a predetermined concentration.
  • Tomato (Lycopersicon esculentum) seedlings planted in a container are allowed to lay eggs for about 24 hours by releasing adult tobacco whitefly. This seedling is stored for 8 days, and the larvae are hatched from the delivered eggs. The diluted solution is sprayed on the seedlings at a rate of 10 mL / seedling. After 7 days, the number of surviving insects is examined, and the control value is obtained by the following formula.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Tai number of live insects at the time of investigation in the treated group
  • Test Example 5 As a result of conducting the test according to Test Method 5 using the following present compound as a test compound at a predetermined concentration of 500 ppm, all of the following present compounds showed a control value of 90% or more.
  • Test Example 6 As a result of testing according to Test Method 6 using the following present compound as a test compound at a predetermined concentration of 500 ppm, all of the following present compounds showed a mortality rate of 90% or more.
  • Test method 7 A test compound is prepared in accordance with the method described in Formulation Example 5, and water containing 0.03% by volume of Cyndine (registered trademark) is added thereto to prepare a diluted solution containing the test compound at a predetermined concentration. About 40 adult spider mites are released on kidney bean (Phaseolus vulgaris) seedlings (first true leaf development stage) planted in a container. After 1 day, the diluted solution is sprayed on the seedlings at a rate of 10 mL / seedling. After 7 days, the number of live insects is examined, and the control value is calculated by the following formula.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Tai Number of live insects at the time of survey in the treated group It means a group that operates in the same manner as the treatment group except that the test compound is not used.
  • Test Example 7 As a result of conducting a test according to Test Method 7 using the following present compound as a test compound at a predetermined concentration of 500 ppm, the following present compound showed a control value of 90% or more.
  • Compound of the present invention 2
  • Test Example 8 As a result of testing according to Test Method 8 using the following present compound as a test compound at a predetermined concentration of 3.5 ppm, all of the following present compounds showed a mortality rate of 91% or more.
  • Test method 9 A test compound is prepared according to the method described in Formulation Example 5, water is added thereto, and a diluted solution containing the test compound at a predetermined concentration is prepared.
  • the predetermined concentration is either 500 ppm, 125 ppm, 31 ppm or 7.8 ppm.
  • Test Example 9 As a result of testing according to Test Method 9 using the following present compound as a test compound at a predetermined concentration of 500 ppm, all of the following present compounds showed a mortality rate of 80% or more.
  • Test method 10 A test compound is prepared according to the method described in Formulation Example 5, water is added thereto, and a diluted solution containing the test compound at a predetermined concentration is prepared.
  • the predetermined concentration is either 500 ppm, 125 ppm, 31 ppm or 7.8 ppm.
  • Test Example 10 As a result of testing according to Test Method 10 using the following present compound as a test compound at a predetermined concentration of 500 ppm, all of the following present compounds showed a mortality rate of 100%.
  • Test method 11 An acetone solution prepared so that the test compound is 200 ppm is poured into a container having an internal volume of 20 mL, and the inner surface of the container is uniformly coated so that the test compound has a predetermined concentration, and then dried.
  • the percentage of moribund insects (%) (number of moribund insects / number of test insects) x 100
  • Test Example 11 As a result of performing the test according to Test Method 11 using the following present compound as a test compound at a predetermined concentration of 10 mg / m 2 , all of the following present compounds showed a mortality rate of 80% or more.
  • Test method 12 An acetone solution prepared so that the test compound is 200 ppm is poured into a container having an internal volume of 20 mL, and the inner surface of the container is uniformly coated so that the test compound has a predetermined concentration, and then dried.
  • the percentage of moribund insects (%) (number of moribund insects / number of test insects) x 100
  • Test Example 12 As a result of conducting the test according to Test Method 12 using the following present compound as a test compound at a predetermined concentration of 10 mg / m 2 , all of the following present compounds showed a mortality rate of 80% or more.
  • the compound of the present invention exhibits an excellent control effect against harmful arthropods.

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Abstract

La présente invention concerne un composé ayant un excellent effet de lutte contre des arthropodes nuisibles. L'invention concerne un composé représenté par la formule (I) (dans la formule, R représente un groupe méthyle ou un groupe éthyle) ayant un excellent effet de lutte contre des arthropodes nuisibles.
PCT/JP2019/017320 2018-04-25 2019-04-24 Composé de pyrimidine et composition de lutte contre les arthropodes nuisibles le contenant WO2019208598A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07506347A (ja) * 1992-03-14 1995-07-13 ヘキスト・シェーリング・アグレボ・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 置換ピリミジン類，それらの製造方法およびそれらの害虫防除剤および殺菌剤としての用途
JPH08113564A (ja) * 1994-08-23 1996-05-07 Ube Ind Ltd ４−シクロヘキシルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤
JP2000508636A (ja) * 1996-04-03 2000-07-11 ヘキスト・シエーリング・アグレボ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング 置換されたピリジン／ピリミジン、その製法および殺虫剤としてのその使用
JP2002522424A (ja) * 1998-08-01 2002-07-23 アベンティス・クロップサイエンス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング 置換されたシクロへキシルアミノピリミジン類

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Publication number Priority date Publication date Assignee Title
JPH07506347A (ja) * 1992-03-14 1995-07-13 ヘキスト・シェーリング・アグレボ・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 置換ピリミジン類，それらの製造方法およびそれらの害虫防除剤および殺菌剤としての用途
JPH08113564A (ja) * 1994-08-23 1996-05-07 Ube Ind Ltd ４−シクロヘキシルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤
JP2000508636A (ja) * 1996-04-03 2000-07-11 ヘキスト・シエーリング・アグレボ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング 置換されたピリジン／ピリミジン、その製法および殺虫剤としてのその使用
JP2002522424A (ja) * 1998-08-01 2002-07-23 アベンティス・クロップサイエンス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング 置換されたシクロへキシルアミノピリミジン類

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Title
LÜMMEN, P.: "Biochemical aspects of N-heterocyclic complex-I inhibitors with insecticidal activity", BIOCHEMICAL SOCIETY TRANSACTIONS, vol. 27, no. 4, 1999, pages 602 - 606, XP055649853 *
OKUN, J. G.: "Three classes of inhibitors share a common binding domain in mitochondrial complex I (NADH:ubiquinone oxidoreductase", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 274, no. 5, 1999, pages 2625 - 2630, XP055055604, DOI: 10.1074/jbc.274.5.2625 *

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