JP7538380B1 - Ester compounds and their uses - Google Patents

Abstract

で示される化合物は、有害節足動物に対して優れた防除効力を有する。 The present invention provides a compound having excellent control activity against harmful arthropods, represented by formula (I).

The compound represented by the formula (I) has excellent control activity against harmful arthropods.

Description

This patent application claims priority under the Paris Convention based on Japanese Patent Application No. 2023-216471 (filed on December 22, 2023), and the benefit thereof, the entire contents of which are incorporated herein by reference.
The present invention relates to an ester compound and its use.

で示されるエステル化合物（以下、化合物Ａと記す）が記載されている。 In Patent Document 1, a compound represented by the formula (A) is disclosed as having excellent insecticidal activity.

An ester compound represented by the formula (hereinafter referred to as compound A) is described.

Patent No. 3728967

The objective of the present invention is to provide a compound that has excellent control activity against harmful arthropods.

で示される化合物（以下、本発明化合物と記す）。
［２］ ［１］に記載の化合物と、不活性担体とを含有する組成物。
［３］ ［１］に記載の化合物の有効量を有害節足動物又は有害節足動物の生息場所に施用することによる、有害節足動物の防除方法。
［４］ ［１］に記載の化合物と、メトフルトリン及びジメフルトリンからなる群より選ばれる１以上の化合物とを含有する組成物。
［５］ ［１］に記載の化合物又は［４］に記載の組成物と、水、アルコール類、ケトン類、芳香族炭化水素類、脂肪族炭化水素類、エステル類、ニトリル類、エーテル類、アミド類、ハロゲン化炭化水素類、スルホキシド類、鉱物油類及び植物油類からなる群より選ばれる１以上の液体担体とを含有する組成物。
［６］ ［１］に記載の化合物又は［４］に記載の組成物と、アルキル硫酸エステル塩、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アルキルアリールエーテル類、アルキルアリールエーテル類のポリオキシエチレン化物、ポリエチレングリコールエーテル類、多価アルコールエステル類及び糖アルコール誘導体からなる群より選ばれる１以上の界面活性剤とを含有する組成物。
［７］ ［１］に記載の化合物又は［４］に記載の組成物と、カゼイン、ゼラチン、多糖類、リグニン誘導体、ベントナイト、及び合成水溶性高分子からなる群より選ばれる１以上の増粘剤とを含有する組成物。
［８］ ［１］に記載の化合物又は［４］に記載の組成物と、ＢＨＴ（２，６－ジ－ｔ－ブチル－４－メチルフェノール）及びＢＨＡ（２－ｔ－ブチル－４－メトキシフェノールと３－ｔ－ブチル－４－メトキシフェノールとの混合物）からなる群より選ばれる１以上の酸化防止剤とを含有する組成物。
［９］ ［１］に記載の化合物又は［４］に記載の組成物を、植物性粉末に担持させた組成物。
［１０］ ［１］に記載の化合物又は［４］に記載の組成物と、結合剤とを含有する組成物。
［１１］ ［１］に記載の化合物又は［４］に記載の組成物を、コットンリンター及びパルプからなる群より選ばれる１以上の基材に担持させた組成物。
［１２］ ［１］に記載の化合物又は［４］に記載の組成物を、熱可塑性樹脂又は紙に担持させた組成物。
［１３］ ［１］に記載の化合物又は［４］に記載の組成物を含有する、油剤、乳剤、フロアブル剤、エアゾール剤、加熱蒸散剤、非加熱蒸散剤、煙霧剤、及びＵＬＶ剤からなる群より選ばれる製剤。 The present inventors have conducted studies to find a compound having excellent control activity against harmful arthropods, and as a result, have found that the compound represented by the following formula (I) has excellent control activity against harmful arthropods.
The present invention is as follows.
[1] Formula (I):

(hereinafter, referred to as the compound of the present invention).
[2] A 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 the harmful arthropods or to a habitat of the harmful arthropods.
[4] A composition comprising the compound according to [1] and one or more compounds selected from the group consisting of metofluthrin and dimefluthrin.
[5] A composition comprising the compound according to [1] or the composition according to [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 [1] or the composition according to [4], and one or more surfactants selected from the group consisting of alkyl sulfate salts, alkyl sulfonate salts, alkylaryl sulfonate salts, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
[7] A composition comprising the compound according to [1] or the composition according to [4] and one or more thickeners 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 [1] or the composition according to [4], and one or more antioxidants selected from the group consisting of BHT (2,6-di-t-butyl-4-methylphenol) and BHA (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol).
[9] A composition comprising the compound according to [1] or the composition according to [4] supported on a plant powder.
[10] A composition comprising the compound according to [1] or the composition according to [4] and a binder.
[11] A composition comprising the compound according to [1] or the composition according to [4] supported on one or more substrates selected from the group consisting of cotton linters and pulp.
[12] A composition in which the compound according to [1] or the composition according to [4] is supported on a thermoplastic resin or paper.
[13] A preparation containing the compound according to [1] or the composition according to [4], the preparation being selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heated evaporation preparations, non-heated evaporation preparations, aerosols, and ULV preparations.

The present invention makes it possible to control harmful arthropods.

The compound of the present invention has one or more stereoisomers. 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.

で示される化合物及び式（ＩＩＩ）：

で示される化合物が挙げられる。 The optical isomer of the compound of the present invention includes, for example, a compound represented by the formula (II):

and a compound of formula (III):

Examples of the compound include those represented by the following formula:

As the compound of the present invention, it is preferable to use the optical isomer represented by formula (II) or a mixture of isomers rich in said optical isomer.

The geometric isomer of the compound of the present invention includes, for example, the compound represented by formula (IV).

で示される化合物及び式（ＶＩ）：

で示される化合物が挙げられる。 As the optical isomer of the compound represented by formula (IV), for example, the compound represented by formula (V):

and compounds of formula (VI):

Examples of the compound include those represented by the following formula:

As the compound of the present invention, it is preferable to use a geometric isomer represented by formula (I) or a mixture of isomers rich in said geometric isomer, and it is even more preferable to use a geometric isomer represented by formula (V) or a mixture of isomers rich in said geometric isomer.

The embodiments of the compound of the present invention include the following compounds.
A compound represented by formula (II):
A mixture comprising a compound represented by formula (II) and a compound represented by formula (III).
A mixture of optical isomers enriched in the optical isomer represented by formula (II).
A mixture comprising a compound represented by formula (I) and a compound represented by formula (IV).
A mixture of geometric isomers containing an enriched amount of the geometric isomer represented by formula (I).
A mixture comprising a compound represented by formula (II) and a compound represented by formula (V).
A mixture of geometric isomers containing an enriched geometric isomer represented by formula (II).

The composition according to one embodiment of the present invention is a composition containing the compound of the present invention and an inert carrier. The composition is usually prepared by mixing the compound of the present invention with an inert carrier such as a solid carrier or a liquid carrier, and adding a surfactant or other formulation auxiliary as necessary to prepare an emulsion, oil, powder, granule, wettable powder, wettable granule, flowable, dry flowable, microcapsule, etc.
The composition generally contains the compound of the present invention in an amount of 0.0001 to 95% by weight based on the total weight of the composition.

Examples of solid carriers used in formulation include fine powders and granules of 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.), and synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethylmethacrylate, polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, etc.).

Examples of liquid carriers 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.).

Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers or their salts (polyoxyethylene alkyl ether sulfate ammonium salts), polyoxyethylene alkyl aryl ethers or their salts, and polyethylene glycol fatty acid esters, as well as anionic surfactants such as alkyl sulfonates, alkyl benzene sulfonates, and alkyl sulfates.

Other formulation adjuvants include adhesives, dispersants, colorants and stabilizers, such as casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, 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).

The compound of the present invention can control harmful arthropods such as harmful insects and harmful mites. Specific examples include the following.

Hemiptera: Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodes orizicolus, Stenocranus pacificus, and other Delphacidae; Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Empoasca onukii, Empoasca fabae, Dalbulus maidis, Cofana spectra, Amrasca biguttula biguttula, and other Cicadellidae; Aphrophoridae, such as Philaenus spumarius; Cercopidae, such as Mahanarva posticata and Mahanarva fimbriolata; Aphis fabae, Aphis glycines, Aphis gossypii, Aphis pomi, Aphis spiraecola, Myzus myzus, and other aphids. persicae, wheat straw aphid (Brachycaudus helichrysi), radish aphid (Brevicoryne brassicae), rosy apple aphid (Dysaphis plantaginea), false radish aphid (Lipaphis erysimi), tulip aphid (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), wheat curl aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus black aphid (Toxoptera citricida), peach butterbur aphid (Hyalopterus pruni), barnyard millet aphid (Melanaphis sacchari, Tetraneura nigriabdominalis, Ceratovacuna lanigera, Eriosoma lanigerum, English grain aphid (Sitobion avenae), etc. Aphididae; Daktulosphaira vitifoliae, Phylloxera devastatrix, Phylloxera notabilis, Phylloxera russelae, etc. Phylloxeridae; Adelges tsugae, Adelges piceae, Aphrastasia Adelgidae, such as 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 Pentatomidae, such as Piezodorus melacanthus and Piezodorus hybneri; Cydnidae, such as Scaptocoris castanea; Alydidae, such as Riptortus clavatus, Leptocorisa chinensis and Leptocorisa acuta; Coreidae, such as Cletus punctiger and Leptoglossus australis; Cavelius saccharivorus, Togo Lygaeidae family such as Blissus leucopterus, Trigonotylus caelestialium, Stenotus rubrovittatus, Stenodema calcarata, Lygus lineolaris, Miridae family such as Trialeurodes vaporariorum, Bemisia tabaci, Dialeurodes citri, Aleurocanthus spiniferus, Aleurocanthus Aleyrodidae, such as Pealius euryae, Abgrallaspis cyanophylli, Aonidiella aurantii, Diaspidiotus perniciosus, Pseudaulacaspis pentagona, Unaspis yanonensis, Unaspis citri, Coccidae, Ceroplastes rubens, Icerya purchasi, Icerya seychellarum and other Margarodidae; Phenacoccus solani, Phenacoccus solenopsis, Planococcus kraunhiae, Pseudococcus comstocki, Planococcus citri, Pseudococcus calceolariae, Pseudococcus longispinus, Brevennia rehi and other Pseudococcidae; Diaphorina citri, Trioza erytreae, Cacopsylla Psyllidae, such as Cacopsylla pyrisuga, Cacopsylla chinensis, Bactericera cockerelli, and Cacopsylla pyricola; Tingidae, such as Corythucha ciliata, Corythucha marmorata, Stephanitis nashi, and Stephanitis pyrioides; Cimicidae, such as Cimex lectularius and Cimex hemipterus; Cicadidae, such as Quesada gigas; Triatoma infestans, Triatoma The family Reduviidae includes the Assassin Bug (Rhodonius prolixus), Triatoma dimidiata, and the Venezuelan Assassin Bug (Rhodonius rubrofasciata).

Lepidoptera: Chilo suppressalis, Chilo polychrysus, Scirpophaga innotata, Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis, Marasmia exigua, Notarcha derogata, Ostrinia furnacalis, Ostrinia nubilalis, Hellula undalis, Herpetogramma luctuosale, Parapediasia Crambidae, such as Nymphula depunctalis, Diatraea saccharalis, and Leucinodes orbonalis; Pyralidae, such as Elasmopalpus lignosellus, Plodia interpunctella, Euzophera batangensis, and Cadra cautella; Spodoptera litura, Spodoptera exigua, Mythimna separata, Mamestra brassicae, and Sesamia inferens, Spodoptera mauritia, Naranga aenescens, Spodoptera frugiperda, Spodoptera exempta, Spodoptera cosmioides, Spodoptera eridania, Agrotis ipsilon, Agrotis segetum, Autographa nigrisigna, Plusia festucae, Soybean looper, Trichoplusia spp., Heliothis spp. such as Heliothis virescens, Helicoverpa armigera, Helicoverpa spp. such as corn earworm (Helicoverpa zea), Noctuidae such as velvet bean caterpillar (Anticarsia gemmatalis), cotton leafworm (Alabama argillacea), hop wine borer (Hydraecia immanis), Pieridae such as cabbage white butterfly (Pieris rapae), pear fruit moth (Grapholita molesta), plum fruit moth (Grapholita dimorpha), bean fruit moth (Leguminivora glycinivorella), adzuki bean pea moth (Matsumuraeses azukivora), apple smaller tortrix moth (Adoxophyes orana fasciata), tea smaller tortrix moth (Adoxophyes honmai), tea tortrix moth (Homona Tortricidae such as Archips fuscocupreanus, Cydia pomonella, Tetramoera schistaceana, Epinotia aporema, Citrus fruit borer, Lobesia botrana; Gracilariae such as Caloptilia theivora and Phyllonorycter ringoniella; Carposinidae such as Carposina sasakii; Coffee leaf miner, Lyonetia clerkella, Lyonetia Lyonetiidae such as Lymantria dispar and Euproctis pseudoconspersa; Plutellidae such as Plutella xylostella; Gelechiidae such as Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, Tuta absoluta; Hyphantria Arctiidae such as Telchin licus (Giant sugar cane borer); Cossidae such as Cossus insularis (Cossus insularis); Geometridae such as Ascotis selenaria (Ascotis selenaria); Limacodidae such as Parasa lepida (Parasa lepida); Stathmopodidae such as Stathmopoda masinissa (Stathmopoda masinissa); Sphingidae such as Acherontia lachesis (Acherontia lachesis); Nokona feralis (Nokona feralis), Synanthedon hector (Synanthedon tenuis; Hesperiidae, such as Parnara guttata; Tineidae, such as Tinea translucens and Tineola bisselliella.

Thysanoptera: Thripidae, such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, Echinothrips americanus, Scirtothrips perseae; Phlaeothripidae, such as Haplothrips aculeatus.

Diptera: Anthomyiidae, such as Delia platura, Delia antiqua, and Pegomya cunicularia; Ulidiidae, such as Tetanops myopaeformis; Agromyzidae, such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticola; Chloropidae, such as Chlorops oryzae; Bactrocera Tephritidae, such as Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratitis capitata, Rhagoletis pomonella, and Rhacochlaena japonica; Ephydridae, such as Hydrellia griseola, Hydrellia philippina, and Hydrellia sasakii; Drosophila suzukii, Drosophila japonica ... Drosophilidae, such as Drosophila melanogaster and Drosophila suzukii; Phoridae, such as Megaselia spiracularis; Psychodidae, such as Clogmia albipunctata; Sciaridae, such as Bradysia difformis and Bradysia odoriphaga; Cecidomyiidae, such as Mayetiola destructor and Orseolia oryzae; Diopsidae, such as Diopsis macrophthalma; Tsetse flies, such as Glossina palpalis and Glossina morsitans. (Glossinidae); Simuliidae such as Simulium japonicum and Simulium damnosum; Phlebotominae; Tipulidae such as Tipula aino, Tipula oleracea, and Tipula paludosa; Culex pipiens pallens, Culex tritaeniorhynchus, Culex pipiens f. molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, and Aedes albopictus. Culicidae such as Aedes aegypti, Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles minimus; Simulidae such as Prosimulium yezoensis and Simulium ornatum; Tabanidae such as Tabanus trigonus; Musca domestica, Muscina The family Muscidae, such as Stomoxys stabulans, Stomoxys calcitrans, and Haematobia irritans; the family Calliphoridae; the family Sarcophagidae; the family Chironomidae, such as Chironomus plumosus, Chironomus yoshimatsui, and Glyptotendipes tokunagai; the family Fannidae.

Coleoptera: Diabrotica spp. (e.g., Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded cucumber beetle (Diabrotica balteata), Cucumber beetle (Diabrotica speciosa), etc.), Bean leaf beetle (Cerotoma trifurcata), Red-necked leaf beetle (Oulema melanopus), Cucumber leaf beetle (Aulacophora femoralis), Striped flea beetle (Phyllotreta striolata), Cabbage free beetle (Phyllotreta cruciferae), Western black free beetle (Phyllotreta pusilla, Cabbage stem free beetle (Psylliodes chrysocephala), Hop free beetle (Psylliodes punctulata), Colorado potato beetle (Leptinotarsa decemlineata), Rice leaf beetle (Oulema oryzae), Grape colaspis (Colaspis brunnea), Corn free beetle (Chaetocnema pulicaria), Sweet potato spur beetle (Chaetocnema confinis), Potato free beetle (Epitrix cucumeris), Rice spur beetle (Dicladispa armigera), Southern corn leaf beetle (Myochrous denticollis), Four-legged tortoise beetle (Laccoptera quadrimaculata), Tobacco flea beetle (Epitrix hirtipennis), Radish beetle (Phaedon The family Chrysomelidae, such as the seed corn beetle (Stenolophus lecontei) and the slender seed corn beetle (Clivina impressifrons); the family Carabidae, such as the beetle Anomala cuprea, the beetle Anomala rufocuprea, the beetle Anomala albopilosa, the beetle Popillia japonica, the beetle Heptophylla picea, the European chafer (Rhizotrogus majalis), the beetle Tomarus gibbosus, the beetle Holotrichia spp., and the beetle Phyllophaga crinita. Scarabaeidae, such as Diloboderus spp., Diloboderus abderus, etc.; Anthriibidae, such as Araecerus coffeae; Aponidae, such as Cylas formicarius; Bruchidae, such as Zabrotes subfasciatus; Scolytidae, such as Tomicus piniperda, Coffee berry borer (Hypothenemus hampei); Euscepes postfasciatus, Hypera postica, Sitophilus zeamais, rice weevil (Sitophilus oryzae), granarian rice weevil (Sitophilus granarius), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), white-spotted weevil (Rhabdoscelus lineaticollis), boll weevil (Anthonomus grandis), grass striped weevil (Sphenophorus venatus), southern cornbill bug (Sphenophorus callosus), soybean stalk weevil (Sternechus subsignatus), sugarcane weevil (Sphenophorus levis), rust gourd weevil (Scepticus griseus), brown gourd weevil (Scepticus uniformis), Aracanthus mourei, and other Aracanthus spp., and the cotton root borer (Eutinobothrus brasiliensis), etc.; Tenebrionidae, such as Tribolium castaneum, Tribolium confusum, and Alphitobius diaperinus; Coccinellidae, such as Epilachna vigintioctopunctata, etc.; Bostrychidae, such as Lyctus brunneus and Rhizopertha dominica, etc.; Ptinidae; Anoplophora Cerambycidae, such as Aromia bungii, Migdolus fryanus, Melanotus okinawensis, Agriotes fuscicollis, Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., Aeolus spp., Elateridae, such as Paederus fuscipes and other Staphylinidae; Dermestidae such as Anthrenus verbasci, Dermestes maculates, and Trogoderma granarium; Anobiidae such as Lasioderma serricorne and Stegobium paniceum; Laemophloeidae such as Cryptolestes ferrugineus; Silvanidae such as Oryzaephilus surinamensis; Blossom beetle Brassicogethes Nitidulidae family, such as Nitidulidus aeneus.

Orthoptera: Migratory locust (Locusta migratoria), Moroccan grasshopper (Dociostaurus maroccanus), Australian grasshopper (Chortoicetes terminifera), Red grasshopper (Nomadacris septemfasciata), Brown locust (Locustana pardalina), Tree locust (Anacridium melanorhodon), Italian locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two-striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-legged grasshopper (Melanoplus femurrubrum), Clear-winged grasshopper (Camnula pellucida), Desert grasshopper (Schistocerca The grasshopper family (Acrididae) includes the common grasshopper (Austracris guttulosa), the yellow-winged locust (Gastrimargus musicus), the sparse-throated locust (Austracris guttulosa), the oriental grasshopper (Oxya yezoensis), the long-winged grasshopper (Oxya japonica), and the Taiwan grasshopper (Patanga succincta); the mole cricket family (Gryllotalpidae) includes the mole cricket (Gryllotalpa orientalis); the field cricket family (Gryllidae) includes the European house cricket (Acheta domestica) and the field cricket (Teleogryllus emma); and the katydid family (Tettigoniidae) includes the Mormon cricket (Anabrus simplex).

Hymenoptera: Tenthredinidae, such as Athalia rosae and Athalia japonica; Solenopsis spp., such as Solenopsis invicta and Solenopsis geminata; Atta spp., such as Atta capiguara, Acromyrmex spp., Paraponera clavata, Ochetellus glaber, Monomorium pharaonis, Linepithema humile, Formica japonica, Pristomyrmex punctutus, Pheidole noda, Pheidole megacephala, Camponotus japonicus, Camponotus obscuripes, and other Camponotus spp., Pogonomyrmex spp., Pogonomyrmex occidentalis, Wasmania spp., Wasmania auropunctata, and other Formicidae, Anoplolepis gracilipes, and other Formicidae; Vespa mandarinia, Vespa simillima, Vespa analis, Vespa Vespidae, such as Polistes velutina and Polistes jokahamae; Siricidae, such as Urocerus gigas; Bethylidae.

Order of Cockroaches (Blattodea): Family Ectobiidae such as the German cockroach (Blattella germanica); Family Blattidae such as the American cockroach (Periplaneta fuliginosa), the American cockroach (Periplaneta americana), the American cockroach (Periplaneta australasiae), the brown cockroach (Periplaneta brunnea), and the Asian cockroach (Blatta orientalis); Family Reticulitermes speratus, Formosanus formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, Neotermes Termites of the family Termitidae, such as Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus, Reticulitermes miyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, and Cornitermes cumulans.

Order Siphonaptera: Family Pulicidae such as the human flea (Pulex irritans), cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis), rat flea (Xenopsylla cheopis), and chicken flea (Echidnophaga gallinacea); Family Hectopsyllidae such as the sand flea (Tunga penetrans); Family Ceratophyllidae such as the European rat flea (Nosopsyllus fasciatus).

Order Psocodae: Pediculidae, such as the head louse (Pediculus humanus capitis); Pthiridae, such as the human pubic louse (Pthirus pubis); Haematopinidae, such as the cow louse (Haematopinus eurysternus) and the pig louse (Haematopinus suis); Linognathidae, such as the cow louse (Linognathus vituli), the sheep trunk louse (Linognathus ovillus), and the cow louse (Solenopotes capillatus); Bovicola bovis, sheep louse (Bovicola ovis), Bovicola breviceps, Damalinia Bovicoliidae, such as Trichodectes canis and Felicola subrostratus; Menoponidae, such as Menopon gallinae, Menacanthus stramineus, and Trinoton spp.; Trimenoponidae, such as Cummingsia spp.; Trogiidae, such as Trogium pulsatorium; Liposcelis corrodens, Liposcelis Liposcelididae (also called Liposcelididae) such as Liposcelis bostrychophila, Liposcelis pearmani, and Liposcelis entomophila.

Thysanura: Family Lepismatidae, including the Japanese silverfish (Ctenolepisma villosa) and the European silverfish (Lepisma saccharina).

Acari: Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligonychus spp. and other Tetranychidae; Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculus spp. Eriophyidae, such as Aceria diospyri, Aceria tosichella, and Shevtchenkella sp.; Tarsonemidae, such as Polyphagotarsonemus latus; Tenuipalpidae, such as Brevipalpus phoenicis; Tuckerellidae; Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Rocky Mountain Wood Tick (Dermacentor andersoni), Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Black-legged Tick (Ixodes scapularis), Western Black-legged Tick (Ixodes pacificus), Ixodes holocyclus, Ixodes ricinus, Lone Star Tick (Amblyomma americanum), Gulf Coast Tick (Amblyomma maculatum), Rhipicephalus microplus, Cattle Tick (Rhipicephalus annulatus), Brown Dog Tick (Rhipicephalus sanguineus), Rhipicephalus appendiculatus, Rhipicephalus Ixodidae such as Argas persicus, Ornithodoros hermsi, Ornithodoros turicata; Acaridae such as Tyrophagus putrescentiae and Tyrophagus similis; Pyroglyphidae such as Dermatophagoides farinae and Dermatophagoides pteronyssinus; Cheyletus eruditus, Cheyletus malaccensis, Chelacaropsis moorei, Cheyletiella Cheyletidae such as Psoroptes ovis, Psoroptes equi, Knemidocoptes mutans, Otodectes cynotis, Chorioptes spp. and other Psoroptidae; Sarcoptidae such as Notoedres cati, Notoedres muris, Sarcoptes scabiei and other Sarcoptidae; Listrophorus gibbus and other Listrophoridae; Dermanyssus Dermanyssidae such as Ornithonyssus gallinae; Macronyssidae such as Ornithonyssus sylviarum and Ornithonyssus bacoti; Varroidae such as Varroa jacobsoni; Demodex canis and Demodex cati; Trombiculidae such as Leptotrombidium akamushi, Leptotrombidium pallidum, and Leptotrombidium scutellare.

Order Araneae: Family Eutichuridae such as Cheiracanthium japonicum; Family Theridiidae such as Latrodectus hasseltii.
Polydesmida: Paradoxosomatidae, including Oxidus gracilis, Nedyopus tambanus, etc.
Isopoda: Family Armadillidiidae, including Armadillidium vulgare.
Chilopoda: Scutigeridae such as Thereuonema hilgendorfi; Scolopendridae such as Scolopendra subspinipes; Ethopolyidae such as Bothropolys rugosus.

Harmful arthropods such as harmful insects and harmful mites may be harmful arthropods such as harmful insects and harmful mites that have reduced sensitivity to insecticides, acaricides, etc. or have developed resistance to such drugs.

A composition according to one embodiment of the present invention is a composition (hereinafter referred to as composition A) containing the compound of the present invention and at least one compound selected from the group consisting of metofluthrin and dimefluthrin. Metofluthrin and dimefluthrin can be used alone or in combination of two types. In addition, metofluthrin and dimefluthrin each have one or more stereoisomers, and the metofluthrin and dimefluthrin used in the present invention include stereoisomers and mixtures thereof.
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 dimefluthrin is not particularly limited, but may be, in terms of mass ratio (compound of the present invention:at least one compound selected from the group consisting of metofluthrin and dimefluthrin), 100,000:1 to 1:100,000, 50,000:1 to 1:50,000, , 10,000:1 to 1:10,000, 1,000:1 to 1:1000, 500:1 to 1:500, 100:1 to 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, and the like.

Metofluthrin and dimefluthrin are known to have excellent control effects against harmful arthropods such as harmful insects and harmful mites. Therefore, composition A containing at least one compound selected from the group consisting of metofluthrin and dimefluthrin is expected to have excellent control effects against harmful arthropods. Examples of harmful arthropods that can be controlled by composition A include those mentioned above.

The method for controlling harmful arthropods of the present invention is carried out by applying an effective amount of the compound of the present invention or composition A directly to the harmful arthropods and/or to the habitat of the harmful arthropods (plants, soil, inside a house, animals, etc.). Examples of the method for controlling harmful arthropods of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, fumigation treatment, water surface treatment, and seed treatment.

When the compound of the present invention or composition A is used for controlling harmful arthropods in the agricultural field, the application amount is usually 1 to 10,000 g of the compound of the present invention per 10,000 m ^2. When the compound of the present invention or composition A is formulated as an emulsifiable concentrate, wettable powder, flowable agent or the like, it is usually applied after diluting with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm (for example, 1,000 ppm), and granules, dusts, etc. are usually applied as they are.

When the compound of the present invention or composition A is used for controlling harmful arthropods living in houses, the application amount is usually 0.01 to 1000 mg of the compound of the present invention per ^m2 of treatment area when applied on a surface, and usually 0.01 to 500 mg of the compound of the present invention per ^m3 of treatment space when applied in a space. When the compound of the present invention or composition A is formulated as an emulsifiable concentrate, wettable powder, flowable agent, etc., it is usually applied after diluting with water so that the active ingredient concentration is 0.1 to 10000 ppm, and oil solutions, aerosols, fumigants, poison baits, etc. are applied as they are.

The compound of the present invention or composition A is usually used as a composition further containing an inert carrier (hereinafter referred to as composition B). Composition B is usually prepared by mixing the compound of the present invention or composition A with a liquid carrier, a surfactant, etc., and adding formulation auxiliaries such as a thickener, a binder, a dispersant, a stabilizer, and a gas, if necessary, to be used as an oil solution, an emulsion, a wettable powder, a flowable agent (suspension in water, emulsion in water, etc.), a powder, a granule, an aerosol agent (direct spray type, space spray type, metered spray type, one-push type, total spray type, intermittent spray type, etc.), a spray, an electric spray (ultrasonic vibration type, electrostatic spray type, etc.), a heated transpiration agent (incense stick, electric mat, liquid-absorbing wick type heated transpiration agent, etc.), a non-heated transpiration agent (resin transpiration agent, impregnated paper transpiration agent, net preparation, etc.), a fog agent (fogging, etc.), ULV (Ultra Low Volume) agent, etc.
A formulation that is one embodiment of the present invention is a formulation containing the compound of the present invention or Composition A, which is selected from the group consisting of an oil solution, an emulsion, a flowable agent, an aerosol agent, a heated evaporation agent, a non-heated evaporation agent, a fog agent, and a ULV agent.
These preparations usually contain the compound of the present invention or composition A in an amount of 0.0001 to 99% by weight based on the total weight of the preparation.

Examples of liquid carriers 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, trichloromethane, carbon tetrachloride, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), mineral oils (kerosene, kerosene, diesel, etc.), and vegetable oils (soybean oil, cottonseed oil, etc.).
A composition according to 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. A formulation according to one embodiment of the present invention is a formulation containing the composition and selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heat evaporation agents, and ULV agents.

Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
The composition according to 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 sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives. Also, the formulation according to one embodiment of the present invention is a formulation containing the composition and selected from the group consisting of emulsions, flowables, and heat-transferables.

Examples of thickeners include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, and synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.).
A composition according to 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. A formulation according to one embodiment of the present invention is a flowable preparation containing the composition.

Antioxidants include, for example, BHT (2,6-di-tert-butyl-4-methylphenol) and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
A composition which is 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. Also, a formulation which is one embodiment of the present invention is a formulation which contains the composition and is selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heated transpiration agents, non-heated transpiration agents, aerosols, and ULV agents.

The composition according to one embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on a vegetable powder (wood flour, meal powder, etc.). The vegetable powder may be used by mixing the vegetable powder with a binder (tab flour, starch, gluten, etc.). The preparation according to one embodiment of the present invention is a heat-transpirable agent containing the composition.
A composition according to another embodiment of the present invention is a composition containing the compound of the present invention or composition A and a binder. A preparation according to one embodiment of the present invention is a heat-transferable agent containing the composition.

The composition according to one embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on one or more substrates selected from the group consisting of cotton linters and pulp. Specific examples of the substrate include cotton linters solidified into a plate shape and fibers of a mixture of cotton linters and pulp solidified into a plate shape. The formulation according to one embodiment of the present invention is a heat-transpirable agent containing the composition.

The composition according to one 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 or paper. Also, the preparation according to one embodiment of the present invention is a non-heated evaporative agent containing the composition.
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 copolymer; ethylene-methacrylic acid ester copolymers such as ethylene-methyl methacrylate copolymer and ethylene-ethyl methacrylate copolymer; ethylene-acrylic acid ester copolymers such as ethylene-methyl acrylate copolymer and ethylene-ethyl acrylate copolymer; ethylene-vinyl carboxylic acid copolymers such as ethylene-acrylic acid copolymer; ethylene-tetracyclododecene copolymer; polypropylene resins such as propylene polymers and propylene-ethylene copolymers; poly-4-methylpentene-1, polybutene-1, polybutadiene, polystyrene, and acrylonitrile-styrene resins; acrylonitrile-styrene resins such as ethylene-vinyl carboxylic acid copolymers; Examples of the resin include styrene-based elastomers such as styrene-conjugated diene copolymers and hydrogenated styrene-conjugated diene block copolymers; fluororesins; 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 polycyclohexylene dimethylene terephthalate; polycarbonate, polyacetal, polyacrylsulfone, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride, and polyurethane. These resins may be used alone or in combination of two or more. If necessary, plasticizers such as phthalates (dimethyl phthalate, dioctyl phthalate, and the like), adipic acid esters, and stearic acid may be added to these resins.
Examples of the paper include filter paper and Japanese paper.
The composition which is 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.
A composition which is yet another embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on paper.

The present invention will be explained in more detail below with reference to manufacturing examples and test examples, but the present invention is not limited to these examples.

First, a production example of the compound of the present invention will be shown.

Production Example 1
To a mixture of 1.10 g of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylate (1.10 g) produced by the method described in Production Example 1 of JP-A-2004-269507, 10 mL of chloroform, and 1.36 mL of methanol, 15.3 mL of titanium tetrachloride (1.0 M toluene solution) was added and stirred at room temperature for 1 hour. A saturated aqueous solution of sodium bicarbonate was added to the resulting mixture, and the mixture was extracted with tert-butyl methyl ether. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting 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).

The ¹ H-NMR data of the compound 1 of the present invention is shown below.
¹ H-NMR (CDCl ₃ ) 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).

Next, the efficacy of the compound of the present invention against harmful arthropods is demonstrated by test examples.

Test Example 1
An acetone solution prepared so that the test compound was 12.5 ppm was poured into a 20 mL container, and the test compound was uniformly coated on the inner surface of the container so that the test compound was 0.63 mg/m ² , and then dried for 76 hours.
Ten adult females of the house ant were placed in the container, and the lid was closed. After one hour, the condition of the house ant was examined and the mortality rate was calculated by the following formula.
Mortality rate (%) = (Number of dead insects/Number of tested insects) x 100
The test was repeated three times, and the average mortality rate was calculated.
As a result, when the compound 1 of the present invention was used as the test compound, the mortality rate (average value of three repetitions) was 67%.

Comparative Example 1
Instead of the compound 1 of the present invention, compound A described in Japanese Patent No. 3728967 (Patent Document 1) was used as a test compound, and the test was carried out in the same manner as in Test Example 1. The mortality rate (average value of three repetitions) was 7%.

The compound of the present invention exhibits excellent control effects against harmful arthropods.

Claims (13)

Formula (I):

A compound represented by the formula: A composition comprising the compound of claim 1 and an inert carrier. A method for controlling arthropod pests by applying an effective amount of the compound described in claim 1 to the arthropod pests or to the habitat of the arthropod pests. A composition comprising the compound according to claim 1 and one or more compounds selected from the group consisting of metofluthrin and dimefluthrin. 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. 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 sulfonate salts, alkylaryl sulfonate salts, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives. A composition comprising the compound according to claim 1 or the composition according to claim 4 and one or more thickeners selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite, and synthetic water-soluble polymers. 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-t-butyl-4-methylphenol) and BHA (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol). A composition comprising the compound according to claim 1 or the composition according to claim 4 supported on a plant powder. A composition comprising the compound according to claim 1 or the composition according to claim 4 and a binder. A composition comprising the compound according to claim 1 or the composition according to claim 4 supported on one or more substrates selected from the group consisting of cotton linters and pulp. A composition comprising the compound according to claim 1 or the composition according to claim 4 supported on a thermoplastic resin or paper. A preparation containing the compound according to claim 1 or the composition according to claim 4, the preparation being selected from the group consisting of an oil solution, an emulsion, a flowable agent, an aerosol, a heated vaporization agent, a non-heated vaporization agent, a fog agent, and an ULV agent.