Ester compounds and uses thereof

Abstract

The present invention provides a compound having excellent control effect on harmful arthropods. The compound represented by formula (I) has excellent control effect on harmful arthropods. #imgabs0#

Description

Technical Field

[0001] This patent application claims the priority and benefits provided for by the Paris Convention based on Japanese Patent Application No. 2023-216471 (filed on December 22, 2023), the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to ester compounds and uses thereof. Background Art

[0003] Patent Document 1 describes an ester compound represented by formula (A) (hereinafter referred to as compound A) as a compound having excellent insecticidal activity.

[0004] [Chemical formula 1]

[0005]

[0006] Prior art literature

[0007] Patent Literature

[0008] Patent Document 1: Japanese Patent No. 3728967 Summary of the invention

[0009] Problems to be solved by the invention

[0010] An object of the present invention is to provide a compound having an excellent control effect on harmful arthropods.

[0011] Means for solving problems

[0012] The inventors of the present application have conducted studies to find a compound having an excellent control effect on harmful arthropods, and as a result, have found that a compound represented by the following formula (I) has an excellent control effect on harmful arthropods.

[0013] The present invention is as follows.

[0014] [1] A compound represented by formula (I) (hereinafter referred to as the compound of the present invention).

[0015] [Chemical formula 2]

[0016]

[0017] [2] A composition comprising the compound described in [1] and an inactive carrier.

[0018] [3] A method for controlling harmful arthropods, which is carried out by applying an effective amount of the compound described in [1] to the harmful arthropods or a habitat of the harmful arthropods.

[0019] [4] A composition comprising the compound according to [1] and one or more compounds selected from the group consisting of metofluthrin and transfluthrin.

[0020] [5] A composition comprising the compound described in [1] or the composition described in [4], and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils and vegetable oils.

[0021] [6] A composition comprising the compound described in [1] or the composition described in [4], and one or more surfactants selected from the group consisting of alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylene compounds of alkyl aryl ethers, polyethylene glycol ethers, polyol esters, and sugar alcohol derivatives.

[0022] [7] A composition comprising the compound described in [1] or the composition described in [4], and one or more thickeners selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite and synthetic water-soluble polymers.

[0023] [8] A composition comprising the compound described in [1] or the composition described in [4], and one or more antioxidants selected from the group consisting of BHT (2,6-di-tert-butyl-4-methylphenol) and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

[0024] [9] A composition obtained by supporting the compound according to [1] or the composition according to [4] on a plant powder.

[0025]

[10] A composition comprising the compound according to [1] or the composition according to [4], and a binder.

[0026]

[11] A composition obtained by supporting the compound according to [1] or the composition according to [4] on one or more substrates selected from the group consisting of cotton linters and pulp.

[0027]

[12] A composition obtained by supporting the compound according to [1] or the composition according to [4] on a thermoplastic resin or paper.

[0028]

[13] A preparation containing the compound described in [1] or the composition described in [4], wherein the preparation is selected from the group consisting of oil, emulsion, flowable, aerosol, heated transpiration agent, non-heated transpiration agent, mist and ULV agent.

[0029] Effects of the Invention

[0030] According to the present invention, harmful arthropods can be controlled. DETAILED DESCRIPTION

[0031] The compounds of the present invention may have one or more stereoisomers. Examples of stereoisomers include optical isomers and geometric isomers. The present invention includes each optical isomer, each geometric isomer, and a mixture of isomers in any ratio.

[0032] Examples of the optical isomers of the compound of the present invention include a compound represented by formula (II) and a compound represented by formula (III).

[0033] [Chemical formula 3]

[0034]

[0035] [Chemical formula 4]

[0036]

[0037] As the compound of the present invention, it is preferred to use an optical isomer represented by formula (II) or an isomer mixture containing a large amount of the optical isomer.

[0038] Examples of the geometrical isomers of the compound of the present invention include compounds represented by formula (IV).

[0039] [Chemical formula 5]

[0040]

[0041] Examples of the optical isomers of the compound represented by formula (IV) include a compound represented by formula (V) and a compound represented by formula (VI).

[0042] [Chemical formula 6]

[0043]

[0044] [Chemical formula 7]

[0045]

[0046] As the compound of the present invention, it is preferred to use a geometric isomer represented by formula (I) or an isomer mixture containing a large amount of the geometric isomer, and it is more preferred to use a geometric isomer represented by formula (V) or an isomer mixture containing a large amount of the geometric isomer.

[0047] As embodiments of the compound of the present invention, the following compounds can be mentioned.

[0048] A compound represented by formula (II).

[0049] A mixture comprising a compound represented by formula (II) and a compound represented by formula (III).

[0050] A mixture of optical isomers containing a large amount of the optical isomer represented by formula (II).

[0051] A mixture comprising a compound represented by formula (I) and a compound represented by formula (IV).

[0052] A mixture of geometric isomers containing a large number of geometric isomers represented by formula (I).

[0053] A mixture comprising a compound represented by formula (II) and a compound represented by formula (V).

[0054] A mixture of geometric isomers containing a large amount of the geometric isomer represented by formula (II).

[0055] The composition as one embodiment of the present invention is a composition containing the compound of the present invention and an inactive carrier. The aforementioned composition is usually a mixture of the compound of the present invention and an inactive carrier such as a solid carrier, a liquid carrier, a surfactant, and other preparation adjuvants as needed, and is formulated into emulsions, oils, powders, granules, wettable powders, water-dispersible granules, flowables, dry suspensions, microcapsules, etc.

[0056] The aforementioned composition usually contains 0.0001 to 95% by weight of the compound of the present invention based on the total weight of the composition.

[0057] Examples of the solid carrier used in formulation include clays (kaolin clay, diatomaceous earth, bentonite, acid clay, etc.), dry silica, wet silica, talc, ceramics, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), fine powders and granules, and synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, etc.).

[0058] Examples of the liquid carrier include water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (toluene, xylene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, etc.), ethers (diisopropyl ether, diethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), and vegetable oils (soybean oil, cottonseed oil, etc.).

[0059] Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether or salts thereof (polyoxyethylene alkyl ether ammonium sulfate), polyoxyethylene alkyl aryl ether or salts thereof, and polyethylene glycol fatty acid esters; and anionic surfactants such as alkyl sulfonates, alkylbenzene sulfonates, and alkyl sulfates.

[0060] Examples of other formulation adjuvants include fixatives, dispersants, colorants, stabilizers, and the like, and specific examples include casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, BHT (2,6-di-tert-butyl-4-methylphenol), and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

[0061] The compound of the present invention can control harmful arthropods such as harmful insects and harmful mites. Specifically, the following examples are given.

[0062] Hemiptera: Laodelphax striatellus, Nilaparvatalugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodesorizicolus, Stenocranus pacificus, etc. Delphacidae; Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Empoasca onukii, Empoasca fabae, Dalbulus nigropictus maidis), white-winged brown-veined leafhopper (Cofanaspectra), two-spotted green leafhopper (Amrasca biguttula biguttula), etc.; Aphrophoridae (Aphrophoridae) such as yellow-headed long-leaf hopper (Philaenus spumarius); Cercopidae (Cercopidae) such as bubble blower (Mahanarva posticata) and sugarcane hopper (Mahanarva fimbriolata);Beet aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), apple aphid (Aphis pomi), spiraea aphid (Aphis spiraecola), peach aphid (Myzus persicae), plum short-tailed aphid (Brachycaudus helichrysi), cabbage aphid (Brevicoryne brassicae), rose apple aphid (Dysaphis plantaginea), cabbage stalked aphid (Lipaphis erysimi), potato long-stalked aphid (Macrosiphum euphorbiae), eggplant ditch aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), cereal stalked aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus aphid (Toxoptera citricida), peach pink aphid (Hyalopterus pruni), sorghum aphid (Melanaphis sacchari, Tetraneura nigriabdominalis, Ceratovacuna lanigera, Eriosoma lanigerum, Sitobion avenae, etc. Aphididae; Daktulosphaira vitifoliae, Phylloxera devastatrix, Phylloxera notabilis, Phylloxera russelae, etc. Phylloxeridae; Adelgidae, Adelges tsugae, Adelges piceae, Aphrastasia pectinatae, etc.Scotinophara lurida, Scotinophara coarctata, Nezara antennata, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Eysarcoris annamita, Halyomorpha halys, Nezara viridula, Euschistus heros, Piezodorus guildinii, Oebalus pugnax, Dichelops melacanthus, Piezodorus hybneri, etc. Pentatomidae; Scaptocoris scaptocoris castanea) and other Cydnidae; Alydidae such as Riptortus clavatus, Leptocorisa chinensis and Leptocorisa acuta; Coreidae such as Cletus punctiger and Leptoglossus australis; Lygaeidae such as Cavelerius saccharivorus, Togohemipterus and Blissus leucopterus; Trigonotylus caelestialium, Stenotus rubrovittatus and Stenodema calcarata), Lygus lineolaris, etc.; Aleyrodidae, etc.;Tea long round scale (Abgrallaspis cyanophylli), red round scale (Aonidiella aurantii), pear round scale (Diaspidiotusperniciosus), mulberry white scale (Pseudaulacaspispentagona), arrow-pointed shield scale (Unaspis yanonensis), citrus sharp shield scale (Unaspis citri) and other shield scales (Diaspididae); red wax scale (Ceroplastes rubens) and other scales (Coccidae); blowing cotton scale (Icerya purchasi), silver-haired blowing cotton scale (Icerya seychellarum) and other cotton scales (Margarodidae); Lycoris powdery mildew scale (Phenacoccus solani), hibiscus powdery mildew scale (Phenacoccussolenopsis), Japanese hip-shaped powdery mildew scale (Planococcus Pseudococcidae, such as Pseudococcus kraunhiae, Pseudococcus comstocki, Planococcus citri, Pseudococcus calceolariae, Pseudococcus longispinus, Brevennia rehi; Psyllidae, such as Diaphorina citri, Trioza erytreae, Cacopsylla pyrisuga, Cacopsylla chinensis, Bactericera cockerelli, Cacopsylla pyricola; Corythucha ciliata, Corythucha chrysanthemum marmorata), Stephanitis nashi, Stephanitis pyrioides, etc.; Cimicidae, such as Cimex lectularius and Cimex hemipterus; Cicadidae, such as Quesada gigas;Triatoma infestans, Triatoma rubrofasciata, Triatoma dimidiata, Rhodonius prolixus and other Reduviidae bugs. ;

[0063] Lepidoptera: Chilo suppressalis, Chilopolychrysus, Scirpophaga innotata, Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis, Marasmia exigua, Notarcha derogata, Ostrinia furnacalis, Ostrinia nubilalis, Hellulaundalis, Herpetogramma luctuosale), bluegrass stem borer (Parapedia siateterrellus), rice borer (Nymphuladepunctalis), sugarcane borer (Diatraea saccharalis), eggplant borer (Leucinodes orbonalis) and other grass borers (Crambidae); small corn borer (Elasmopalpuslignosellus), Indian grain moth (Plodia interpunctella), leather dark moth (Euzophera batangensis), powdery moth (Cadra cautella) and other moths (Pyralidae);Spodoptera litura, Spodoptera exigua, Mythimna separata, Mamestrabrassicae, Sesamia inferens, Spodoptera mauritia, Naranga aenescens, Spodoptera frugiperda, Spodoptera exempta, Spodoptera cosmioides, Spodoptera eridania, Agrotis ipsilon, Agrotis segetum, Autographanigrisigna, Plusia festucae, Chrysodeixis includens, Trichoplusia spp., Heliothis virescens, Heliothis spp., Helicoverpa armigera, Helicoverpa zea, Anticarsia gemmatalis, Alabamaargillacea, Hydraecia immanis, etc.; Pieridae, Pierisrapae, etc.;Pear borer (Grapholita molesta), sand apple borer (Grapholita dimorpha), soybean borer (Leguminivora glycinivorella), Japanese bean moth (Matsumuraeses azukivora), apple leaf roller (Adoxophyesorana fasciata), tea leaf roller (Adoxophyes honmai), tea long moth (Homona magnanima), apple yellow moth (Archipsfuscocupreanus), apple leaf roller (Cydia pomonella), yellow borer (Tetramoera schistaceana), bean shoot borer (Epinotia aporema), citrus fruit fly (Citripestissagittiferella), grape flower wing moth (Lobesia botrana) and other moths (Tortricidae); tea moth (Caloptilia theivora), golden moth (Phyllonorycter ringoniella and other Gracilariidae; Carposinidae and other fruit borers Carposina sasakii; Lyonetiidae and other leafminers Leucoptera coffeella, Lyonetia clerkella, Lyonetia prunifoliella; Lymantriidae and other Lymantria spp., Lymantria dispar and other Lymantriidae; Plutellidae and other Plutella xylostella; Anarsialineatella, Helcystogramma triannulella, Pectinophoragossypiella, Phthorimaea spp. operculella), tomato moth (Tutaabsoluta) and other moths of the Gelechiidae family; American white moth (Hyphantria cunea) and other moths of the Arctiidae family; sugarcane borer (Telchin licus) and other moths of the Castniidae family;Cossidae, such as Cossus insularis; Geometridae, such as Ascotis selenaria; Limacodidae, such as Parasalepida; Stathmopodidae, such as Stathmopoda masinissa; Sphingidae, such as Acherontia lachesis; Sesiidae, such as Nokonaferalis, Synanthedon hector, Synanthedon tenuis; Hesperiidae, such as Parnara guttata; Tineidae, such as Tinea translucens, Tineola bisselliella.

[0064] Thysanoptera: Thripidae, including Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, Echinothrips americanus, and Scirtothrips perseae; Phlaeothripidae, including Haplothrips aculeatus.

[0065] Diptera: Anthomyiidae such as Delia platura, Delia antiqua, Pegomya cunicularia; Ulidiidae such as Tetanopsmyopaeformis; Agromyzidae such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, Chromatomyiahorticola; Chloropidae such as Chloropsoryzae; Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae), Bactroceratryoni, Ceratitis capitata, Rhagoletis pomonella, Rhacochlaena japonica, etc.; Ephydridae, Hydrelliagriseola, Hydrellia philippina, Hydrelliasasakii, etc.; Drosophilidae, Drosophila suzukii, Drosophilamelanogaster, etc.; Phoridae, Megaselia spiracularis, etc.; Psychodidae, Clogmia albipunctata, etc.; Bradysia difformis), Bradysia odoriphaga, etc.; Cecidomyiidae, etc.; Diopsidae, etc.;Glossinidae, such as Glossina palpalis and Glossina morsitans; Simuliidae, such as Simulium japonicum and Simulium damnosum; Phlebotominae; Tipulidae, such as Tipula aino, Tipula oleracea and Tipulapaludosa; Culex pipiens pallens, Culextritae niorhynchus, Culex pipiens f.molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, Aedes albopictus and Aedes aegypti. aegypti, Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles undaicus, Anopheles arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles minimus, etc.; Simulidae, such as Prosimulium yezoensis and Simulium ornatum; Tabanidae, such as Tabanus trigonus; Musca domestica, Muscina stabulans), Stomoxyscalcitrans, Haematobia irritans, etc.; Muscidae; Calliphoridae; Sarcophagidae;Chironomus plumosus, Chironomusyoshimatsui, Glyptotendipes tokunagai, etc. Chironomidae; Fannidae.

[0066] Coleoptera: Diabrotica spp. (e.g. Diabrotica virgifera virgifera, Diabrotica undecimpunctatahowardi, Diabrotica barberi, Diabrotica virgiferazeae, Diabrotica balteata, Diabrotica speciosa, etc.), Cerotoma trifurcata, Oulemamelanopus, Aulacophora femoralis, Phyllotreta striolata, Phyllotreta cruciferae, Phyllotreta pusilla, Psylliodes chrysocephala), Psylliodes punctulata, Leptinotarsa ​​decemlineata, Oulema oryzae, Colaspis brunnea, Chaetocnema pulicaria, Chaetocnema confinis, Epitrix cucumeris, Dicladispa armigera, Myochrous denticollis, Laccoptera quadrimaculata, Epitrix hirtipennis, Phaedon brassicae, Medythianigrobilineata, etc.; Seedcorn beetle (Stenolophus lecontei), corn seed beetle (Clivina impressifrons), etc. Carabidae;Scarabaeidae such as Anomala cuprea, Anomala rufocuprea, Anomala albopilosa, Popillia japonica, Heptophyllapicea, Rhizotrogus majalis, Tomarus gibbosus, Holotrichia spp., Phyllophaga crinita, Diloboderus abderus, etc.; Anthriiibidae such as Araecerus coffeae; Cylas ant beetle formicarius, Aponidae; Brazilian bean weevil (Zabrotessubfasciatus), Bruchidae; Scolytidae; Tomicus piniperda, Hypothenemus hampei; West Indian sweet potato weevil (Euscepespostfasciatus), alfalfa weevil (Hypera postica), corn weevil (Sitophilus zeamais), rice weevil (Sitophilus oryzae), grain weevil (Sitophilus granarius), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), palm weevil (Rhabdoscelus lineaticollis), cotton boll weevil (Anthonomus grandis), parasitic grain weevil (Sphenophorus venatus), southern corn long-beaked weevil (Sphenophorus callosus), soybean stem weevil (Sternechus subsignatus), sugarcane weevil (Sphenophorus levis), gourd rust weevil (Scepticus griseus), Scepticus uniformis, Aracanthus mourei, Aracanthus spp., cotton root borer (Eutinobothrus brasiliensis), etc.Tenebrionidae such as Tribolium castaneum, Tribolium confusum, and Alphitobius diaperinus; Coccinellidae such as Epilachna vigintioctopunctata; Bostrychidae such as Lyctus brunneus and Rhizopertha dominica; Ptinidae; Cerambycidae such as Anoplophora malasiaca, Migdolus fryanus, and Aromiabungii; Melanotus okinawensis, Agriotes fuscicollis, and Melanotus horned Elateridae, such as Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., and Aeolus spp.; Staphylinidae, such as Paederus fuscipes; Dermestidae, such as Anthrenus verbasci, Dermestes maculates, and Trogoderma granarium; Anobiidae, such as Lasioderma serricorne and Stegobium paniceum; Cryptolestes spp., such as Cryptolestes spp., and Aeolus spp. ferrugineus) and other flat grain beetles (Laemophloeidae); Suriname saw-toothed grain beetles (Oryzaephilus surinamensis) and other saw-toothed grain beetles (Silvanidae); rapeseed beetles (Brassicogethesaeneus) and other saw-toothed grain beetles (Nitidulidae).

[0067] Orthoptera: Migratory locust (Locusta migratoria), Moroccan halberd locust (Dociostaurus maroccanus), Australian plague locust (Chortoicetes terminifera), Red-winged locust (Nomadacrisseptemfasciata), Brown migratory locust (Locustana pardalina), Tree locust (Anacridium melanorhodon), Italian locust (Calliptamus italicus), Long-fronted locust (Melanoplus differentialis), Two-banded grasshopper (Melanoplus bivittatus), Migrant grasshopper (Melanoplus sanguinipes), Red-legged grasshopper (Melanoplus femurrubrum), Clear-winged earth locust (Camnula pellucida), Desert locust (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Small-winged rice grasshopper (Oxya yezoensis, Oxya japonica, Patanga succincta, etc.; Gryllotalpidae, such as Gryllotalpa orientalis, etc.; Gryllidae, such as Acheta domestica, Teleogryllus emma, etc.; Tettigoniidae, such as Anabrus simplex, etc.

[0068] Hymenoptera: Tenthredinidae, including Athalia rosae and Athalia japonica; Solenopsis spp., including Solenopsis invicta and Solenopsis geminata; Atta spp., including Brown leaf-cutting ants (Attacapiguara), Acromyrmex spp., Paraponera clavata, Ochetellus glaber, Monomoriumpharaonis, Linepithema humile, Formica japonica, Pristomyrmex punctutus, Pheidole spp. noda), Pheidolemegacephala, Camponotus japonicus, Camponotus obscuripes, Pogonomyrmex occidentalis, Wasmania auropunctata, Anoplolepis gracilipes, etc.; Vespidae; Urocerus spp.; Vespa simillima, Vespa analis, Vespavelutina, Polistes jokahamae; gigas) and other tree wasps (Siricidae); Bethylidae.

[0069] Blattodea: Blattella germanica and other Ectobiidae; Periplaneta fuliginosa, Periplaneta americana, Periplaneta australasiae, Periplaneta brunnea, Blattaorientalis and other Blattidae; Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, Neotermes koshunensis, Glyptotermes satsumensis), Nakajima termites, Glyptotermesnakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus, Reticulitermes miyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, Cornitermes cumulans, etc., belong to the Termitidae family.

[0070] Order Siphonaptera: Human flea (Pulex irritans), cat flea (Ctenoce phalides felis), dog flea (Ctenocephalides canis), rat flea (Xenopsylla cheopis), avian flea (Echidnophaga gallinacea) (Pulicidae); Tunga penetrans (Hectopsyllidae); European rat flea (Nosopsyllus fasciatus) (Ceratophyllidae).

[0071] Psocodae: Pediculus humanus capitis (Pediculidae); Pthirus pubis (Pthiridae); Haematopinus eurysternus (Haematopinus suis) (Haematopinidae); Linognathus vituli (Linognathus vituli), Linognathus ovillus (Linognathus ovillus), Solenopotescapillatus (Solenopotescapillatus) (Linognathidae); Bovicola bovis (Bovicola bovis), Bovicola breviceps (Bovicola breviceps), Damalinia forficula, Werneckiella spp. (Bovicoliidae); Trichodectes canis, Felicola subrostratus, etc.; Menoponidae, such as Menopon gallinae, Menacanthus stramineus, Trinoton spp.; Trimenoponidae, such as Cummingsia spp.; Trogiidae, such as Trogium pulsatorium; Liposcelidae or Liposcelididae, such as Liposcelis corrodens, Liposcelis bostrychophila, Liposcelis pearmani, Liposcelisentomophila.

[0072] Thysanura: Lepismatidae such as Ctenolepisma villosa and Lepismasaccharina.

[0073] Acari: Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligonychus spp., etc. Tetranychidae; Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculus schlechtendali, Aceria diospyri), Aceria tosichella, Shevtchenkella sp., etc. Eriophyidae; Polyphagotarsonemus latus, etc. Tarsonemidae; Brevipalpus phoenicis, etc. Tenuipalpidae; Tuckerellidae;Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Dermacentor andersoni, Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Ixodes pacificus, Ixodes holocyclus, Ixodes ricinus, Amblyomma americanum, Amblyomma maculatum, Rhipicephalus microplus, Rhipicephalus annulatus, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus decoloratus; Argasidae, Argas persicus, Ornithodoros hermsi, Ornithodorosturicata; Acaridae, Tyrophagus putrescentiae, Tyrophagus similis; Pyroglyphidae, Dermatophagoides farinae, Dermatophagoides pteronyssinus; Cheyletus eruditus, Cheyletus malaccus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, Cheyletus serratus, malaccensis), Chelacaropsis moorei, Cheyletiella yasguri, etc.Psoroptes ovis, Psoroptes equi, Knemidocoptes mutans, Otodectes cynotis, Chorioptes spp., etc. of the Psoroptidae family; Notoedres cati, Notoedres muris, Sarcoptes scabiei, etc. of the Sarcoptidae family; Listrophorus gibbus, etc. of the Listrophoridae family; Dermanyssus gallinae, etc. of the Dermanyssidae family; Ornithonyssus sylviarum, Ornithonyssus bacoti, etc. of the Macronyssidae family; Varroa jacobsoni) and other Varroidae; Demodicidae such as Demodex canis and Demodex cati; Trombiculidae such as Leptotrombidium akamushi, Leptotrombidium pallidum and Leptotrombidium scutellare. ;

[0074] Araneae: Cheiracanthium japonicum and other spiders of the family Eutichuridae; Latrodectus hasseltii and other spiders of the family Theridiidae.

[0075] Order Polydesmida: Greenhouse millipedes (Oxidus gracilis), Red millipedes (Nedyopustambanus), etc. Paradoxosomatidae.

[0076] Isopoda: Common beetle (Armadillidium vulgare), etc. Armadillidiidae.

[0077] Class Chilopoda: Scutigeridae such as Thereuonema hilgendorfi; Scolopendridae such as Scolopendra subspinipes; Ethopolyidae such as Bothropolys rugosus.

[0078] The harmful arthropods such as harmful insects and harmful mites may be those whose sensitivity to pesticides, miticides, etc. has been reduced or those that are highly resistant to pesticides.

[0079] The composition as one embodiment of the present invention is a composition containing the compound of the present invention and at least one compound selected from the group consisting of metofluthrin and dimefluthrin (hereinafter referred to as composition A). Metofluthrin and dimefluthrin may be used alone or in combination. In addition, there are one or more stereoisomers in each of metofluthrin and dimefluthrin, and the metofluthrin and dimefluthrin used in the present invention include stereoisomers and mixtures thereof.

[0080] In composition A, the ratio of the compound of the present invention to at least one compound selected from the group consisting of metofluthrin and transfluthrin is not particularly limited, and the ratio by mass ratio (compound of the present invention: at least one compound selected from the group consisting of metofluthrin and transfluthrin) may be 100000:1 to 1:100000, 50000:1 to 1:50000, 10000:1 to 1:10 ... :10000, 1000:1~1:1000, 500:1~1:500, 100:1~1:100, 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.

[0081] It is known that metofluthrin and transfluthrin each have excellent control effects on harmful arthropods such as harmful insects and harmful mites. Therefore, it is expected that the composition A containing at least one compound selected from the group consisting of metofluthrin and transfluthrin will have excellent control effects on harmful arthropods. Examples of harmful arthropods that can be controlled by the composition A include the aforementioned harmful arthropods.

[0082] As the method for controlling harmful arthropods of the present invention, an effective amount of the compound of the present invention or composition A can be directly applied to harmful arthropods and / or applied to the habitats of harmful arthropods (plants, soil, houses, animals, etc.). As the method for controlling harmful arthropods of the present invention, for example, stem and leaf treatment, soil treatment, root treatment, spray treatment, fumigation treatment, water surface treatment and seed treatment can be cited.

[0083] When the compound or composition A of the present invention is used for controlling harmful arthropods in agricultural fields, the application rate is 10000 m 2 The amount of the compound of the present invention is usually 1 to 10000 g. When the compound of the present invention or composition A is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water to a concentration of 0.01 to 10000 ppm (e.g., 1000 ppm) of the active ingredient and applied, and granules, powders, etc. are usually applied directly.

[0084] When the compound or composition A of the present invention is used to control harmful arthropods living in houses, the application amount is, when treating on the surface, 100% water per 1 m 2 The amount of the compound of the present invention applied to the treatment area is usually 0.01 to 1000 mg. When the treatment is carried out in space, the amount is 0.01 to 1000 mg per 1 m 3 The amount of the compound of the present invention to be treated in the space is usually 0.01 to 500 mg. When the compound of the present invention or composition A is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water to a concentration of 0.1 to 10000 ppm of the active ingredient and applied directly, or an oil, aerosol, fumigant, poison bait, etc.

[0085] The compound of the present invention or composition A is usually used in the form of a composition (hereinafter, referred to as composition B) that also contains an inactive carrier. For composition B, the compound of the present invention or composition A can usually be mixed with a liquid carrier, a surfactant, etc., and a thickener, a binder, a dispersant, a stabilizer, a gas, and other preparation adjuvants can be added as needed, and used for oils, emulsions, wettable powders, flowable agents (water suspensions, water emulsions, etc.), powders, granules, aerosols (direct spray type, space spray type, quantitative spray type, One push type, full spray type, intermittent spray type, etc.), sprays, electrosprays (ultrasonic vibration type, electrostatic spray type, etc.), heating transpiration agents (incense sticks, electric mosquito coils, liquid wick type heating transpiration agents, etc.), non-heating transpiration agents (resin transpiration agents, impregnated paper transpiration agents, mesh preparations, etc.), smoke agents (atomizers, etc.), ULV (Ultra Low Volume, ultra-low volume) agents, etc.

[0086] The preparation as one embodiment of the present invention is a preparation selected from the group consisting of oil, emulsion, flowable, aerosol, heated transpiration agent, non-heated transpiration agent, mist and ULV agent, containing the compound or composition A of the present invention.

[0087] These preparations usually contain 0.0001 to 99% by weight of the compound or composition A of the present invention relative to the total weight of the preparation.

[0088] Examples of the liquid carrier include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, phenylxylylethane, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, butyl acetate, methyl oleate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), amides (N,N-dimethylformamide, N,N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, chloroform, carbon tetrachloride, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), mineral oils (kerosene, lamp oil, light oil, etc.), and vegetable oils (soybean oil, cottonseed oil, etc.).

[0089] The composition as one embodiment of the present invention is a composition containing the compound of the present invention or composition A, and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils and vegetable oils. In addition, the preparation as one embodiment of the present invention is a preparation containing the composition, selected from the group consisting of oil, emulsion, flowable agent, aerosol agent, heating evaporative agent and ULV agent.

[0090] Examples of the surfactant include alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylene compounds of alkyl aryl ethers, polyethylene glycol ethers, polyol esters, and sugar alcohol derivatives.

[0091] The composition as one embodiment of the present invention is a composition containing the compound of the present invention or composition A, and one or more surfactants selected from the group consisting of alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylene compounds of alkyl aryl ethers, polyethylene glycol ethers, polyol esters, and sugar alcohol derivatives. In addition, the preparation as one embodiment of the present invention is a preparation selected from the group consisting of an emulsion, a flowable agent, and a heating transpiration agent containing the composition.

[0092] Examples of the thickener include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, and synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.).

[0093] The composition as one embodiment of the present invention is a composition containing the compound of the present invention or composition A, and one or more thickeners selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite and synthetic water-soluble polymers. In addition, the preparation as one embodiment of the present invention is a flowable agent containing the composition.

[0094] Examples of the antioxidant include BHT (2,6-di-tert-butyl-4-methylphenol) and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

[0095] The composition as one embodiment of the present invention is a composition containing the compound of the present invention or composition A and one or more antioxidants selected from the group consisting of BHT and BHA. In addition, the preparation as one embodiment of the present invention is a preparation selected from the group consisting of oil, emulsion, flowable agent, aerosol, heated transpiration agent, non-heated transpiration agent, mist and ULV agent containing the composition.

[0096] The composition as one embodiment of the present invention is a composition obtained by carrying the compound of the present invention or composition A on a plant powder (wood powder, meal powder, etc.). The plant powder can also be used by mixing the above-mentioned plant powder with a binder (red nan powder, starch, gluten, etc.). In addition, the preparation as one embodiment of the present invention is a heating transpiration agent containing the composition.

[0097] A composition as another embodiment of the present invention is a composition comprising the compound or composition A of the present invention and a binder. In addition, a preparation as one embodiment of the present invention is a heat transpiration agent comprising the composition.

[0098] The composition as one embodiment of the present invention is a composition obtained by supporting the compound of the present invention or composition A on one or more substrates selected from the group consisting of cotton linters and pulp. Specifically, the substrate includes, for example, a substrate obtained by solidifying cotton linters into a plate shape and a substrate obtained by solidifying fibers of a mixture of cotton linters and pulp into a plate shape. In addition, a preparation as one embodiment of the present invention is a heating transpiration agent containing the composition.

[0099] A composition as one embodiment of the present invention is a composition obtained by supporting the compound of the present invention or composition A on a thermoplastic resin or paper. In addition, a formulation as one embodiment of the present invention is a non-heating transpiration agent containing the composition.

[0100] Examples of the resin include polyethylene resins such as low-density polyethylene, linear low-density polyethylene, and high-density polyethylene; ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymers; ethylene-methacrylate copolymers such as ethylene-methyl methacrylate copolymers and ethylene-ethyl methacrylate copolymers; ethylene-acrylate copolymers such as ethylene-methyl acrylate copolymers and ethylene-ethyl acrylate copolymers; ethylene-vinyl carboxylic acid copolymers such as ethylene-acrylic acid copolymers; ethylene-tetracyclododecene copolymers; polypropylene resins such as propylene polymers and propylene-ethylene copolymers; poly-4-methyl-1-pentene, poly-1-butene, polybutadiene, polystyrene, acrylonitrile- Styrene resin; styrene elastomers such as acrylonitrile-butadiene-styrene resin, styrene-conjugated diene copolymer, styrene-conjugated diene block copolymer hydrogenate; fluororesin; acrylic resins such as polymethyl methacrylate; polyamide resins such as nylon 6 and nylon 66; polyester resins such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, and polycyclohexanedimethanol terephthalate; polycarbonate, polyacetal, polyacrylic sulfone, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride, and polyurethane. These resins can be used alone or in the form of a mixture of two or more. In these resins, plasticizers such as phthalates (dimethyl phthalate, dioctyl phthalate, etc.), adipic acid esters, and stearic acid can also be added as needed.

[0101] Examples of the paper include filter paper and Japanese paper.

[0102] A composition as another embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on a thermoplastic resin.

[0103] A composition as another embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on paper.

[0104] Example

[0105] Hereinafter, the present invention will be described in more detail using manufacturing examples and test examples, but the present invention is not limited to these examples.

[0106] First, production examples of the compounds of the present invention are shown.

[0107] Production Example 1

[0108] To a mixture of 1.10 g of (1R)-trans-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl ester, 10 mL of chloroform, and 1.36 mL of methanol, 15.3 mL of titanium tetrachloride (1.0 M toluene solution) was added, and the mixture was stirred at room temperature for 1 hour. A saturated sodium bicarbonate aqueous solution was added to the obtained mixture, and extraction was performed with tert-butyl methyl ether. The obtained organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 1.12 g of a compound represented by the following formula (II) (referred to as compound 1 of the present invention).

[0109] [Chemical formula 8]

[0110]

[0111] The following shows the compound 1 of the present invention. 1 H-NMR data.

[0112] 1 H-NMR(CDCl3)δ: 5.69(1H,dt),5.52(1H,dt),5.25(2H,s),4.59(2H,s),3.40( 3H,s),3.33(1H,d),2.11-2.03(2H,m),1.64(3H,s),1.59(3H,s),0.99(3H,t).

[0113] Next, the efficacy of the compound of the present invention against harmful arthropods is demonstrated using Test Examples.

[0114] Test Example 1

[0115] An acetone solution prepared so that the test compound becomes 12.5 ppm is poured into a 20 mL container so that the test compound becomes 0.63 mg / m 2 The coating is evenly applied to the inner surface of the container and then dried for 76 hours.

[0116] Ten female adults of the small yellow house ant were placed in the container and the lid was closed. After one hour, the status of the small yellow house ants was checked and the mortality rate was calculated. The mortality rate was calculated by the following formula.

[0117] Death rate (%) = (number of dead insects / number of test insects) × 100

[0118] The test was repeated 3 times and the average value of the mortality rate was calculated.

[0119] As a result, the insect death rate (average value of 3 replicates) when the present invention compound 1 was used as the test compound was 67%.

[0120] Comparative Example 1

[0121] The test was conducted in the same manner as in Test Example 1 using Compound A described in Japanese Patent No. 3728967 (Patent Document 1) as a test compound instead of Compound 1 of the present invention. As a result, the insect death rate (average value of 3 replicates) was 7%.

[0122] Industrial Applicability

[0123] The compound of the present invention exhibits an excellent control effect on harmful arthropods.

Claims

1. A compound represented by formula (II), 2. A composition comprising the compound according to claim 1 and an inactive carrier.

3. A method for controlling harmful arthropods, which is carried out by applying an effective amount of the compound according to claim 1 to harmful arthropods or a habitat of harmful arthropods. 4 . A composition comprising the compound according to claim 1 and one or more compounds selected from the group consisting of metofluthrin and transfluthrin.

5. A composition comprising the compound according to claim 1 or the composition according to claim 4, and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils and vegetable oils.

6. A composition comprising the compound according to claim 1 or the composition according to claim 4, and one or more surfactants selected from the group consisting of alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylene compounds of alkyl aryl ethers, polyethylene glycol ethers, polyol esters, and sugar alcohol derivatives.

7. A composition comprising the compound according to claim 1 or the composition according to claim 4, and at least one thickener selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite and synthetic water-soluble polymers.

8. A composition comprising the compound according to claim 1 or the composition according to claim 4, and one or more antioxidants selected from the group consisting of BHT (2,6-di-tert-butyl-4-methylphenol) and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

9. A composition obtained by supporting the compound according to claim 1 or the composition according to claim 4 on a plant powder.

10. A composition comprising the compound according to claim 1 or the composition according to claim 4, and a binder.

11. A composition obtained by supporting the compound according to claim 1 or the composition according to claim 4 on one or more substrates selected from the group consisting of cotton linters and pulp.

12. A composition obtained by supporting the compound according to claim 1 or the composition according to claim 4 on a thermoplastic resin or paper.

13. A preparation containing the compound of claim 1 or the composition of claim 4, wherein the preparation is selected from the group consisting of oil, emulsion, flowable, aerosol, heated transpiration, non-heated transpiration, mist and ULV.

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