JP2020152642A - Urea compound and arthropod pest control agent containing the same - Google Patents

Urea compound and arthropod pest control agent containing the same Download PDF

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JP2020152642A
JP2020152642A JP2017138805A JP2017138805A JP2020152642A JP 2020152642 A JP2020152642 A JP 2020152642A JP 2017138805 A JP2017138805 A JP 2017138805A JP 2017138805 A JP2017138805 A JP 2017138805A JP 2020152642 A JP2020152642 A JP 2020152642A
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beetle
compound
aphid
psyllidae
whitefly
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達也 鳥海
Tatsuya Toriumi
達也 鳥海
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Priority to JP2017138805A priority Critical patent/JP2020152642A/en
Priority to ARP180101976 priority patent/AR112453A1/en
Priority to PCT/JP2018/026636 priority patent/WO2019017313A1/en
Publication of JP2020152642A publication Critical patent/JP2020152642A/en
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62Oxygen or sulfur atoms
    • C07D213/69Two or more oxygen atoms

Abstract

To provide a composition exhibiting an excellent effect of controlling arthropod pests.SOLUTION: The compound represented by the formula (1) in the figure has an excellent effect of controlling arthropod pests.SELECTED DRAWING: None

Description

本発明は尿素化合物及びその有害節足動物防除剤に関する。 The present invention relates to urea compounds and their harmful arthropod control agents.

これまでに有害節足動物の防除を目的として、様々な化合物が検討されており、実用に供されている(非特許文献1参照)。 So far, various compounds have been studied for the purpose of controlling harmful arthropods and are put into practical use (see Non-Patent Document 1).

The Pesticide Manual − 16th edition (BCPC刊) ISBN 978−1−901396−86−7The Pesticide Manual-16th edition (published by BCPC) ISBN 978-1-901396-86-7

本発明は、有害節足動物に対して優れた防除効力を有する化合物を提供することを課題とする。 An object of the present invention is to provide a compound having an excellent control effect on harmful arthropods.

本発明は、以下のとおりである。
[1] 式(1)

Figure 2020152642
で示される化合物(以下、化合物A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生物又は有害生物の生息場所に施用する有害生物の防除方法。 The present invention is as follows.
[1] Equation (1)
Figure 2020152642
(Hereinafter referred to as compound A).
[2] A composition containing the compound according to [1] and an inert carrier.
[3] A method for controlling pests by applying an effective amount of the compound according to [1] to a pest or a habitat of the pest.

本発明により、有害節足動物を防除することができる。 According to the present invention, harmful arthropods can be controlled.

本発明の組成物は、化合物Aと不活性担体とを含有する。本発明の組成物は、通常、化合物Aと固体担体、液体担体等の不活性担体とを混合し、必要に応じて界面活性剤、その他の製剤用補助剤を添加して、乳剤、油剤、粉剤、粒剤、水和剤、顆粒水和剤、フロアブル剤、ドライフロアブル剤、マイクロカプセル剤等に製剤化される。 The composition of the present invention contains compound A and an inert carrier. In the composition of the present invention, the compound A is usually mixed with an inert carrier such as a solid carrier or a liquid carrier, and if necessary, a surfactant or other formulation auxiliary is added to form an emulsion, an oil agent, or the like. It is formulated into powders, granules, wettable powders, granule wettable powders, flowable agents, dry flowable agents, microcapsules and the like.

製剤化の際に用いられる固体担体としては、例えば粘土類(カオリンクレー、珪藻土、ベントナイト、フバサミクレー、酸性白土等)、乾式シリカ、湿式シリカ、タルク、セラミック、その他の無機鉱物(セリサイト、石英、硫黄、活性炭、炭酸カルシウム等)、化学肥料(硫安、燐安、硝安、尿素、塩安等)等の微粉末及び粒状物等、並びに合成樹脂(ポリプロピレン、ポリアクリロニトリル、ポリメタクリル酸メチル、ポリエチレンテレフタレート等のポリエステル樹脂、ナイロン−6、ナイロン−11、ナイロン−66等のナイロン樹脂、ポリアミド樹脂、ポリ塩化ビニル、ポリ塩化ビニリデン、塩化ビニル−プロピレン共重合体等)が挙げられる。 Examples of the solid carrier used in the formulation include clays (kaolinkley, diatomaceous earth, bentonite, fubasami clay, acidic white clay, etc.), dry silica, wet silica, talc, ceramics, and other inorganic minerals (serisite, quartz, etc.). Fine powders and granules such as sulfur, activated charcoal, calcium carbonate, etc.), chemical fertilizers (sulfur, phosphorus, diatomaceous earth, urea, salt, etc.), and synthetic resins (polypropylene, polyacrylonitrile, polymethylmethacrylate, polyethylene terephthalate, etc.) Such as polyester resin, nylon-6, nylon-11, nylon-66 and the like, polyamide resin, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer and the like).

液体担体としては、例えば水、アルコール類(メタノール、エタノール等)、ケトン類(アセトン、メチルエチルケトン等)、芳香族炭化水素類(トルエン、キシレン等)、脂肪族炭化水素類(ヘキサン、シクロヘキサン等)、エステル類(酢酸エチル、酢酸ブチル等)、ニトリル類(アセトニトリル等)、エーテル類(ジイソプロピルエーテル、ジエチレングリコールジメチルエーテル等)、アミド類(N,N−ジメチルホルムアミド等)、スルホキシド類(ジメチルスルホキシド等)、及び植物油(大豆油、綿実油等)が挙げられる。 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 (dimethylsulfoxide, etc.), and Examples include vegetable oils (soybean oil, cottonseed oil, etc.).

界面活性剤としては、例えばポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリエチレングリコール脂肪酸エステル等の非イオン界面活性剤、及びアルキルスルホン酸塩、アルキルベンゼンスルホン酸塩、アルキル硫酸塩等の陰イオン界面活性剤が挙げられる。 Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate and alkyl sulfate. Surfactants can be mentioned.

その他の製剤用補助剤としては、固着剤、分散剤、着色剤及び安定剤等、具体的には例えばカゼイン、ゼラチン、糖類(でんぷん、アラビアガム、セルロース誘導体、アルギン酸等)、リグニン誘導体、ベントナイト、合成水溶性高分子(ポリビニルアルコール、ポリビニルピロリドン、ポリアクリル酸類等)、酸性リン酸イソプロピル、2,6−ジ−tert−ブチル−4−メチルフェノール、BHA(2−tert−ブチル−4−メトキシフェノールと3−tert−ブチル−4−メトキシフェノールとの混合物)が挙げられる。 Other pharmaceutical auxiliary agents include fixing agents, dispersants, coloring agents, stabilizers, etc., specifically, for example, casein, gelatin, saccharides (phenols, arabic gum, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, etc. Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acidic isopropyl phosphate, 2,6-di-tert-butyl-4-methylphenol, BHA (2-tert-butyl-4-methoxyphenol) And 3-tert-butyl-4-methoxyphenol).

化合物Aが効力を有する有害生物としては、例えば、以下のものが挙げられる。 Examples of pests for which compound A is effective include the following.

半翅目害虫(Hemiptera):ヒメトビウンカ(Laodelphax striatellus)、トビイロウンカ(Nilaparvata lugens)、セジロウンカ(Sogatella furcifera)、トウモロコシウンカ(Peregrinus maidis)、キタウンカ(Javesella pellucida)、クロフツノウンカ(Perkinsiella saccharicida)、Tagosodes orizicolus等のウンカ科(Delphacidae);ツマグロヨコバイ(Nephotettix cincticeps)、タイワンツマグロヨコバイ(Nephotettix virescens)、クロスジツマグロヨコバイ(Nephotettix nigropictus)、イナズマヨコバイ(Recilia dorsalis)、チャノミドリヒメヨコバイ(Empoasca onukii)、ジャガイモヒメヨコバイ(Empoasca fabae)、コーンリーフホッパー(Dalbulus maidis)、シロオオヨコバイ(Cofana spectra)等のヨコバイ科(Cicadellidae);Mahanarva posticata、Mahanarva fimbriolata等のコガシラアワフキムシ科(Cercopidae);マメクロアブラムシ(Aphis fabae)、ダイズアブラムシ(Aphis glycines)、ワタアブラムシ(Aphis gossypii)、ヨーロッパリンゴアブラムシ(Aphis pomi)、ユキヤナギアブラムシ(Aphis spiraecola)、モモアカアブラムシ(Myzus persicae)、ムギワラギクオマルアブラムシ(Brachycaudus helichrysi)、ダイコンアブラムシ(Brevicoryne brassicae)、Rosy apple aphid(Dysaphis plantaginea)、ニセダイコンアブラムシ(Lipaphis erysimi)、チューリップヒゲナガアブラムシ(Macrosiphum euphorbiae)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、レタスヒゲナガアブラムシ(Nasonovia ribisnigri)、ムギクビレアブラムシ(Rhopalosiphum padi)、トウモロコシアブラムシ(Rhopalosiphum maidis)、ミカンクロアブラムシ(Toxoptera citricida)、モモコフキアブラムシ(Hyalopterus pruni)、ヒエノアブラムシ(Melanaphis sacchari)、オカボノクロアブラムシ(Tetraneura nigriabdominalis)、カンシャワタアブラムシ(Ceratovacuna lanigera)、リンゴワタムシ(Eriosoma lanigerum)等のアブラムシ科(Aphididae);ブドウネアブラムシ(Daktulosphaira vitifoliae)、Pecan phylloxera(Phylloxera devastatrix)、Pecan leaf phylloxera(Phylloxera notabilis)、Southern pecan leaf phylloxera(Phylloxera russellae)等のネアブラムシ科(Phylloxeridae);ツガカサアブラムシ(Adelges tsugae)、Adelges piceae、ヒメカサアブラムシ(Aphrastasia pectinatae)等のカサアブラムシ科(Adelgidae);イネクロカメムシ(Scotinophara lurida)、Malayan rice black bug(Scotinophara coarctata)、アオクサカメムシ(Nezara antennata)、トゲシラホシカメムシ(Eysarcoris aeneus)、オオトゲシラホシカメムシ(Eysarcoris lewisi)、シラホシカメムシ(Eysarcoris ventralis)、ムラサキシラホシカメムシ(Eysarcoris annamita)、クサギカメムシ(Halyomorpha halys)、ミナミアオカメムシ(Nezara viridula)、Brown stink bug(Euschistus heros)、Red banded stink bug(Piezodorus guildinii)、Oebalus pugnax、Dichelops melacanthus等のカメムシ科(Pentatomidae);Burrower brown bug(Scaptocoris castanea)等のツチカメムシ科(Cydnidae);ホソヘリカメムシ(Riptortus pedestris)、クモヘリカメムシ(Leptocorisa chinensis)、ホソクモヘリカメムシ(Leptocorisa acuta)等のホソヘリカメムシ科(Alydidae);ホソハリカメムシ(Cletus punctiger)、アシビロヘリカメムシ(Leptoglossus australis)等のヘリカメムシ科(Coreidae);カンシャコバネナガカメムシ(Caverelius saccharivorus)、コバネヒョウタンナガカメムシ(Togo hemipterus)、アメリカコバネナガカメムシ(Blissus leucopterus)等のナガカメムシ科(Lygaeidae);アカヒゲホソミドリカスミカメ(Trigonotylus caelestialium)、アカスジカスミカメ(Stenotus rubrovittatus)、フタトゲムギカスミカメ(Stenodema calcarata)、サビイロカスミカメ(Lygus lineolaris)等のカスミカメムシ科(Miridae);オンシツコナジラミ(Trialeurodes vaporariorum)、タバココナジラミ(Bemisia tabaci)、ミカンコナジラミ(Dialeurodes citri)、ミカントゲコナジラミ(Aleurocanthus spiniferus)、チャトゲコナジラミ(Aleurocanthus camelliae)、ヒサカキワタフキコナジラミ(Pealius euryae)等のコナジラミ科(Aleyrodidae);シュロマルカイガラムシ(Abgrallaspis cyanophylli)、アカマルカイガラムシ(Aonidiella aurantii)、ナシマルカイガラムシ(Diaspidiotus perniciosus)、クワシロカイガラムシ(Pseudaulacaspis pentagona)、ヤノネカイガラムシ(Unaspis yanonensis)、ニセヤノネカイガラムシ(Unaspis citri)、等のマルカイガラムシ科(Diaspididae);ルビーロウムシ(Ceroplastes rubens)等のカタカイガラムシ科(Coccidae);イセリアカイガラムシ(Icerya purchasi)、キイロワタフキカイガラムシ(Icerya seychellarum)等のワタフキカイガラムシ科(Margarodidae);ナスコナガイガラムシ(Phenacoccus solani)、クロテンコナカイガラムシ(Phenacoccus solenopsis)、フジコナカイガラムシ(Planococcus kraunhiae)、クワコナカイガラムシ(Pseudococcus comstocki)、ミカンコナカイガラムシ(Planococcus citri)、ガハニコナカイガラムシ(Pseudococcus calceolariae)、ナガオコナカイガラムシ(Pseudococcus longispinus)、タトルミーリーバグ(Brevennia rehi)等のコナカイガラムシ科(Pseudococcidae);ミカンキジラミ(Diaphorina citri)、ミカントガリキジラミ(Trioza erytreae)、ナシキジラミ(Cacopsylla pyrisuga)、チュウゴクナシキジラミ(Cacopsylla chinensis)、ジャガイモトガリキジラミ(Bactericera cockerelli)、Pear psylla(Cacopsylla pyricola)等のキジラミ科(Psyllidae);プラタナスグンバイ(Corythucha ciliata)、アワダチソウグンバイ(Corythucha marmorata)、ナシグンバイ(Stephanitis nashi)、ツツジグンバイ(Stephanitis pyrioides)等のグンバイムシ科(Tingidae);トコジラミ(Cimex lectularius)等のトコジラミ科(Cimicidae)及びGiant Cicada(Quesada gigas)等のセミ科(Cicadidae)。 Aphids (Hemiptera): Himetobiunka (Laodelphax striatellus), Tobiirounka (Nilaparvata lugens), Segatella furcifera, Cornunka (Peregrinus maidis), Kitachoka (Javesella pellucida), Kitownka (Javesella pellucida) Aphididae (Delphacidae); Aphid aphid (Nephotettix cincticeps), Aphid aphid (Nephotettix virescens), Aphid aphid (Nephotettix nigropictus), Aphid aphid (Recilia dorsalis), Aphid aphid (Recilia dorsalis), Aphid aphid ), Cicadellidae such as Dalbulus maidis and Cofana spectra; Cercopidae such as Mahanarva posticata and Mahanarva fimbriolata; Aphis aphid, Aphis fabae (Aphis glycines), Wata aphid (Aphis gossypii), European apple aphid (Aphis pomi), Yukiyanagi aphid (Aphis spiraecola), Momoka aphid (Myzus persicae), Wheat aphid (Brachycaudus helichrysi) Rosy apple aphid (Dysaphis plantaginea), fake aphid (Lipaphis erysimi), tulip aphid (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), lettuce aphid (Nasonovia ribisnigri) padi), corn aphididae (Rhopalosiphum maidis), brown marmorated stink bug (Toxoptera citricida), momokofuki aphididae (Hyalopterus pruni), hyeno aphididae (Melanaphis sacchari), stink bug aphididae (Tetraneura nigriabdominalis) Aphididae, such as the brown marmorated stink bug (Eriosoma lanigerum); Daktulosphaira vitifoliae, Pecan phylloxera (Phylloxera devastatrix), Pecan leaf phylloxera (Phylloxera notabilis), Southern pecan leaf phylla (Phylloxeridae); Adelgidae (Adelgidae) such as Adelges tsugae, Adelges piceae, Aphrastasia pectinatae; Scotinophara lurida, Malayan rice black bug (Scotinophara) Stink bug (Nezara antennata), spiny stink bug (Eysarcoris aeneus), stink bug (Eysarcoris lewisi), stink bug (Eysarcoris ventralis), purple stink bug (Eysarcoris aeneus), purple stink bug (Eysarcoris annamita), brown marmorated stink bug (Eysarcoris annamita) Viridula), Brown stink bug (Euschistus heros), Red banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelops melacanthus and other Aphididae (Pentatomidae); Burrower brown bug (Scaptocoris) Whitefly family (Cydnidae) such as castanea; Whitefly family (Alydidae); Whitefly family (Alydidae) such as whitefly (Riptortus pedestris), whitefly (Leptocorisa chinensis), whitefly (Leptocorisa acuta) ), Whitefly (Leptoglossus australis) and other whiteflies (Coreidae); Whitefly (Caverelius saccharivorus), Whitefly (Togo hemipterus), American whitefly (Blissus leuc) Lygaeidae); Redfly whitefly (Trigonotylus caelestialium), Whitefly (Stenotus rubrovittatus), Whitefly (Stenodema calcarata), Sabiirokasumi turtle (Lygus lineolaris) and other whiteflies (Miridae) Whiteflies (Bemisia tabaci), whiteflies (Dialeurodes citri), whiteflies (Aleurocanthus spiniferus), whiteflies (Aleurocanthus camelliae), whiteflies (Pealius euryae), whiteflies (Pealius euryae), etc. Abgrallaspis cyanophylli), whitefly (Aonidiella aurantii), whitefly (Diaspidiotus perniciosus), whitefly (Pseudaulacaspis pentagona), whitefly (Unaspis yanonensis), whitefly (Unaspis yanonensis), whitefly (Unaspis yanonensis) Diaspididae); Whitefly family (Coccidae) such as the whitefly (Ceroplastes rubens); Iseri Psyllidae (Icerya purchasi), Psyllidae (Icerya seychellarum) and other Psyllidae (Phenacoccus solani), Psyllidae (Phenacoccus solenopsis), Psyllidae (Phenacoccus solenopsis), Psyllidae (Phenacoccus solenopsis) Psyllidae scale insect (Pseudococcus comstocki), Psyllidae scale insect (Planococcus citri), Gahaniko scale insect (Pseudococcus calceolariae), Psyllidae scale insect (Pseudococcus longispinus), Psyllidae Psyllidae (Brevennia rehi) Diaphorina citri), scale insect (Trioza erytreae), psyllidae (Cacopsylla pyrisuga), scale insect (Cacopsylla chinensis), scale insect (Bactericera cockerelli), Psyllidae (Psyllidae), Psyllidae (Psyllidae), Psyllidae (Psyllidae) (Corythucha ciliata), Awadachisougunbai (Corythucha marmorata), Nashigunbai (Stephanitis nashi), Tsutsujigunbai (Stephanitis pyrioides) and other Psyllidae (Tingidae); Psyllidae (Cimex lectularius) and other Psyllidae (Cimex lectularius) ) Etc. (Cicadidae).

鱗翅目害虫(Lepidoptera):ニカメイガ(Chilo suppressalis)、Darkheaded stem borer(Chilo polychrysus)、White stem borer(Scirpophaga innotata)、イッテンオオメイガ(Scirpophaga incertulas)、Rupela albina、コブノメイガ(Cnaphalocrocis medinalis)、Marasmia patnalis、イネハカジノメイガ(Marasmia exigua)、ワタノメイガ(Notarcha derogata)、アワノメイガ(Ostrinia furnacalis)、European corn borer(Ostrinia nubilalis)、ハイマダラノメイガ(Hellula undalis)、モンキクロノメイガ(Herpetogramma luctuosale)、シバツトガ(Pediasia teterrellus)、ライスケースワーム(Nymphula depunctalis)、Sugarcane borer(Diatraea saccharalis)等のツトガ科(Crambidae);モロコシマダラメイガ(Elasmopalpus lignosellus)、ノシメマダラメイガ(Plodia interpunctella)等のメイガ科(Pyralidae);ハスモンヨトウ(Spodoptera litura)、シロイチモジヨトウ(Spodoptera exigua)、アワヨトウ(Mythimna separata)、ヨトウガ(Mamestra brassicae)、イネヨトウ(Sesamia inferens)、シロナヨトウ(Spodoptera mauritia)、フタオビコヤガ(Naranga aenescens)、ツマジロクサヨトウ(Spodoptera frugiperda)、アフリカシロナヨトウ(Spodoptera exempta)、タマナヤガ(Agrotis ipsilon)、タマナギンウワバ(Autographa nigrisigna)、イネキンウワバ(Plusia festucae)、Soybean looper(Chrysodeixis includens)、トリコプルシア属(Trichoplusia spp.)、ニセアメリカタバコガ(Heliothis virescens)等のヘリオティス属(Heliothis spp.)、オオタバコガ(Helicoverpa armigera)、アメリカタバコガ(Helicoverpa zea)等のヘリコベルパ属(Helicoverpa spp.)、Velvetbean caterpillar(Anticarsia gemmatalis)、Cotton leafworm(Alabama argillacea)、Hop vine borer(Hydraecia immanis)等のヤガ科(Noctuidae);モンシロチョウ(Pieris rapae)等のシロチョウ科(Pieridae);ナシヒメシンクイ(Grapholita molesta)、スモモヒメシンクイ(Grapholita dimorpha)、マメシンクイガ(Leguminivora glycinivorella)、アズキサヤムシガ(Matsumuraeses azukivora)、リンゴコカクモンハマキ(Adoxophyes orana fasciata)、チャノコカクモンハマキ(Adoxophyes honmai)、チャハマキ(Homona magnanima)、ミダレカクモンハマキ(Archips fuscocupreanus)、コドリンガ(Cydia pomonella)、カンシャシンクイハマキ(Tetramoera schistaceana)、Bean Shoot Borer(Epinotia aporema)、Citrus fruit borer(Ecdytolopha aurantiana)等のハマキガ科(Tortricidae);チャノホソガ(Caloptilia theivora)、キンモンホソガ(Phyllonorycter ringoniella)等のホソガ科(Gracillariidae);モモシンクイガ(Carposina sasakii)等のシンクイガ科(Carposinidae);Coffee Leaf miner(Leucoptera coffeella)、モモハモグリガ(Lyonetia clerkella)、ギンモンハモグリガ(Lyonetia prunifoliella)等のハモグリガ科(Lyonetiidae);マイマイガ(Lymantria dispar)等のリマントリア属(Lymantria spp.)、チャドクガ(Euproctis pseudoconspersa)等のユープロクティス属(Euproctis spp.)等のドクガ科(Lymantriidae);コナガ(Plutella xylostella)等のコナガ科(Plutellidae);モモキバガ(Anarsia lineatella)、イモキバガ(Helcystogramma triannulella)、ワタアカミムシガ(Pectinophora gossypiella)、ジャガイモガ(Phthorimaea operculella)、Tuta absoluta等のキバガ科(Gelechiidae);アメリカシロヒトリ(Hyphantria cunea)等のヒトリガ科(Arctiidae);Giant Sugarcane borer(Telchin licus)等のカストニアガ科(Castniidae);ヒメボクトウ(Cossus insularis)等のボクトウガ科(Cossidae);ヨモギエダシャク(Ascotis selenaria)等のシャクガ科(Geometridae);ヒロヘリアオイラガ(Parasa lepida)等のイラガ科(Limacodidae);カキノヘタムシガ(Stathmopoda masinissa)等のニセマイコガ科(Stathmopodidae);クロメンガタスズメ(Acherontia lachesis)等のスズメガ科(Sphingidae);キクビスカシバ(Nokona feralis)等のスカシバガ科(Sesiidae);イネツトムシ(Parnara guttata)等のセセリチョウ科(Hesperiidae)。 Lepidoptera: Nikameiga (Chilo suppressalis), Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Ittenoomeiga (Scirpophaga incertulas), Rupela albina, Kobunomeiga (Cnaphalocrocis medinal) Snout moth (Marasmia exigua), Watanomeiga (Notarcha derogata), Awanomeiga (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Hymadalanomeiga (Hellula undalis), Monki chronomeiga (Herpetogramma luctuos) Rice case worm (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis) and other snout moths (Crambidae); Morokoshimadarameiga (Elasmopalpus lignosellus), Noshimemadarameiga (Plodia interpunctella) and other snout moths (Pyralidae) , Spodoptera exigua, Awayoto (Mythimna separata), Yotoga (Mamestra brassicae), Rice yoto (Sesamia inferens), Shirona yoto (Spodoptera mauritia), Futaobikoyaga (Naranga aenescens), Crambid snout moth (Naranga aenescens) Spodoptera exempta), Tamanayaga (Agrotis ipsilon), Tamanagin uwaba (Autographa nigrisigna), Inekin uwaba (Plusia festucae), Soybean looper (Chrysodeixis includens), Trichoplusia Heliothis spp., Helliothis virescens, Heliothis spp., Helicoverpa armigera, Helicoverpa zea, Helicoverpa spp., Velvetbean caterpillar, Anticarsia gemmatalis, Noctuidae such as Cotton leafworm (Alabama argillacea) and Hop vine borer (Hydraecia immanis); Pieridae such as Pieris rapae; Nashihimeshinkui (Grapholita molesta), Sumomohimeshinkui (Grapholita dimorpha) Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes honmai, Homona magnanima, Homona magnanima, Homona magnanima, codling moth, codling moth, codling moth, codling moth, codling moth, codling moth, codling moth ), Kansha Sinkuihamaki (Tetramoera schistaceana), Bean Shoot Borer (Epinotia aporema), Citrus fruit borer (Ecdytolopha aurantiana), etc. Tortrix moth (Tortricidae); Chanohosoga (Caloptilia theivora), Kinmonhosoga (Phyllonoryc) Gracillariidae); Codling moth (Carposina sasakii), etc. (Carposinidae); Coffee Leaf miner (Leucoptera coffeella), Momohamogriga (Lyonetia clerkella), Ginmon Hamogriga (Lyonetia prunifoliella), etc. Lymantriidae such as ymantria dispar, Lymantriidae such as Euproctis pseudoconspersa, and Plutellidae such as Plutella xylostella; Tea tussock moth (Anarsia lineatella), gypsy moth (Helcystogramma triannulella), gypsy moth (Pectinophora gossypiella), gypsy moth (Phthorimaea operculella), Tuta absoluta, etc. Twirler moth (Gelechiidae); American white tussock moth (Hyphantria) Gypsy moth (Castniidae) such as Sugarcane borer (Telchin licus); Twirler moth (Cossidae) such as Cossus insularis; Tea tussock moth (Geometridae) such as Ascotis selenaria; Limacodidae; Stahmopoda masinissa and other gypsy mopodidae; Acherontia lachesis and other Sphingidae; Twirler moth (Nokona feralis) and other gypsy moths (Sesiara feralis) Gypsy moth (Hesperiidae) such as guttata).

総翅目害虫(Thysanoptera):ミカンキイロアザミウマ(Frankliniella occidentalis)、ミナミキイロアザミウマ(Thrips palmi)、チャノキイロアザミウマ(Scirtothrips dorsalis)、ネギアザミウマ(Thrips tabaci)、ヒラズハナアザミウマ(Frankliniella intonsa)、イネアザミウマ(Stenchaetothrips biformis)、モトジロアザミウマ(Echinothrips americanus)等のアザミウマ科(Thripidae);イネクダアザミウマ(Haplothrips aculeatus)等のクダアザミウマ科(Phlaeothripidae)。 Thrips palmi (Thysanoptera): Mikankiiro thrips (Frankliniella occidentalis), Minamikiiro thrips (Thrips palmi), Chanokiiro thrips (Scirtothrips dorsalis), Negia thrips (Thrips tabaci) ), Thripidae (Thripidae) such as Thrips palmi Karny (Echinothrips americanus); Thripidae (Phlaeothripidae) such as Thrips aculeatus.

鞘翅目害虫(Coleoptera):ウエスタンコーンルートワーム(Diabrotica virgifera virgifera)、サザンコーンルートワーム(Diabrotica undecimpunctata howardi)、ノザンコーンルートワーム(Diabrotica barberi)、メキシカンコーンルートワーム(Diabrotica virgifera zeae)、バンデッドキューカンバービートル(Diabrotica balteata)、Cucurbit Beetle(Diabrotica speciosa)、ビーンリーフビートル(Cerotoma trifurcata)、クビアカクビホソハムシ(Oulema melanopus)、ウリハムシ(Aulacophora femoralis)、キスジノミハムシ(Phyllotreta striolata)、Cabbage flea beetle(Phyllotreta cruciferae)、Western black flea beetle(Phyllotreta pusilla)、Cabbage stem flea beetle(Psylliodes chrysocephala)、コロラドハムシ(Leptinotarsa decemlineata)、イネドロオイムシ(Oulema oryzae)、グレープ・コラスピス(Colaspis brunnea)、コーン・フレアビートル(Chaetocnema pulicaria)、サツマイモヒサゴトビハムシ(Chaetocnema confinis)、ポテト・フレアビートル(Epitrix cucumeris)、イネトゲハムシ(Dicladispa armigera)、southern corn leaf beetle(Myochrous denticollis)、ヨツモンカメノコハムシ(Laccoptera quadrimaculata)、タバコノミハムシ(Epitrix hirtipennis)等のハムシ科(Chrysomelidae);Seedcorn beetle(Stenolophus lecontei)、Slender seedcorn beetle(Clivina impressifrons)等のオサムシ科(Carabidae);ドウガネブイブイ(Anomala cuprea)、ヒメコガネ(Anomala rufocuprea)、アオドウガネ(Anomala albopilosa)、マメコガネ(Popillia japonica)、ナガチャコガネ(Heptophylla picea)、European Chafer(Rhizotrogus majalis)、クロマルコガネ(Tomarus gibbosus)、Holotrichia属(Holotrichia spp.)、ジューン・ビートル(Phyllophaga crinita)等のPhyllophaga属(Phyllophaga spp.)、Diloboderus abderus等のDiloboderus属(Diloboderus spp.)等のコガネムシ科(Scarabaeidae);ワタミヒゲナガゾウムシ(Araecerus coffeae)、アリモドキゾウムシ(Cylas formicarius)、イモゾウムシ(Euscepes postfasciatus)、アルファルファタコゾウムシ(Hypera postica)、コクゾウムシ(Sitophilus zeamais)、イネゾウムシ(Echinocnemus squameus)、イネミズゾウムシ(Lissorhoptrus oryzophilus)、シロスジオサゾウムシ(Rhabdoscelus lineatocollis)、ワタミハナゾウムシ(Anthonomus grandis)、シバオサゾウムシ(Sphenophorus venatus)、Southern Corn Billbug(Sphenophorus callosus)、Soybean stalk weevil(Sternechus subsignatus)、Sugarcane weevil(Sphenophorus levis)、サビヒョウタンゾウムシ(Scepticus griseus)、トビイロヒョウタンゾウムシ(Scepticus uniformis)、ブラジルマメゾウムシ(Zabrotes subfasciatus)、マツノキクイムシ(Tomicus piniperda)、Coffee Berry Borer(Hypothenemus hampei)、Aracanthus mourei等のAracanthus属(Aracanthus spp.)、cotton root borer(Eutinobothrus brasiliensis)等のゾウムシ科(Curculionidae);コクヌストモドキ(Tribolium castaneum)、ヒラタコクヌストモドキ(Tribolium confusum)等のゴミムシダマシ科(Tenebrionidae);ニジュウヤホシテントウ(Epilachna vigintioctopunctata)等のテントウムシ科(Coccinellidae);ヒラタキクイムシ(Lyctus brunneus)等のナガシンクイムシ科(Bostrychidae);ヒョウホンムシ科(Ptinidae);ゴマダラカミキリ(Anoplophora malasiaca)、Migdolus fryanus等のカミキリムシ科(Cerambycidae);オキナワカンシャクシコメツキ(Melanotus okinawensis)、トビイロムナボソコメツキ(Agriotes fuscicollis)、クシコメツキ(Melanotus legatus)、アシブトコメツキ属(Anchastus spp.)、コノデルス属(Conoderus spp.)、クテニセラ属(Ctenicera spp.)、リモニウス属(Limonius spp.)、Aeolus属(Aeolus spp.)等のコメツキムシ科(Elateridae);アオバアリガタハネカクシ(Paederus fuscipes)等のハネカクシ科(Staphylinidae)。 Coleoptera: Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm (Diabrotica virgifera zeae), Banded cue. Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), Bean Leaf Beetle (Cerotoma trifurcata), Coleoptera beetle (Oulema melanopus), Urihamushi (Aulacophora femoralis), Chrysanthemum beetle (Phyllotreta striolata) black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado beetle (Leptinotarsa decemlineata), Inedro worm (Oulema oryzae), Grape Collaspis (Colaspis brunnea), Grape Collaspis (Colaspis brunnea), Corn flare Beetle (Chaetocnema confinis), potato flare beetle (Epitrix cucumeris), beetle beetle (Dicladispa armigera), south corn leaf beetle (Myochrous denticollis), beetle beetle (Laccoptera quadrimaculata), beetle (Laccoptera quadrimaculata) Chrysomelidae); Seedcorn beetle (Stenolophus lecontei), Slender seedcorn beetle (Clivina impressifrons) and other Coleoptera (Carabidae); Douganebuibui (A) nomala cuprea), Himekogane (Anomala rufocuprea), Anomala albopilosa, Japanese beetle (Popillia japonica), Nagachakogane (Heptophylla picea), European Chafer (Rhizotrogus majalis), Holotrichia (Rhizotrogus majalis), Holotrichia (Tomarus gib) Phyllophaga genus (Phyllophaga spp.) Such as June beetle (Phyllophaga crinita), Diloboderus genus (Diloboderus spp.) Such as Diloboderus abderus, etc. Holotrichia (Scarabaeidae); Watamihigenagazoumushi (Araecerus coffeae) ), Anomala albopilosa (Euscepes postfasciatus), Anomala albopilosa (Hypera postica), Japanese beetle (Sitophilus zeamais), Japanese beetle (Echinocnemus squameus), Japanese beetle (Lissorhoptrus oryzophilus), Japanese beetle (Lissorhoptrus oryzophilus), Japanese beetle Anomala albopilosa (Sphenophorus venatus), Southern Corn Billbug (Sphenophorus callosus), Soybean stalk weevil (Sternechus subsignatus), Sugarcane weevil (Sphenophorus levis), Sabi leopard elephant (Scepticus griseus), Scepticus griseus, Scepticus griseus (Zabrotes subfasciatus), Japanese beetle (Tomicus piniperda), Coffee Berry Borer (Hypothenemus hampei), Aracanthus mourei, etc. s spp.), Cotton root borer (Eutinobothrus brasiliensis), etc. Curculionidae; Click beetle (Tribolium castaneum), Hiratakokunustomodoki (Tribolium confusum), etc. Click beetle family (Tenebrionidae); Nijuyaho Curculionidae (Coccinellidae); Longhorn beetle (Lyctus brunneus), etc. (Bostrychidae); Leopard beetle (Ptinidae); Click beetle (Anoplophora malasiaca), Click beetle (Anoplophora malasiaca), Migdolus fryanus, etc. (Melanotus okinawensis), Click beetle (Agriotes fuscicollis), Longhorn beetle (Melanotus legatus), Click beetle (Anchastus spp.), Conoderus spp., Ctenicera spp. Limonius spp.), Aeolus spp. (Aeolus spp.) And other click beetles (Elateridae);

本発明の有害節足動物の防除方法は、化合物Aの有効量を有害節足動物に直接、及び/又は、有害生物の生息場所(植物、土壌、家屋内等)に施用することにより行われる。 The method for controlling harmful arthropods of the present invention is carried out by applying an effective amount of Compound A directly to harmful arthropods and / or to habitats of harmful organisms (plants, soil, homes, etc.). ..

化合物Aの施用量は、10000m2あたり通常1〜10000gである。化合物Aが乳剤、水和剤、フロアブル剤等に製剤化されている場合は、通常、有効成分濃度が0.01〜10000ppmとなるように水で希釈して施用し、粒剤、粉剤等は、通常、そのまま施用する。 The application rate of Compound A is usually 1 to 10000 g per 10000 m 2 . When compound A is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water so that the concentration of the active ingredient is 0.01 to 10,000 ppm, and the granules, powders, etc. are used. , Usually, apply as it is.

これらの製剤や製剤の水希釈液は、有害節足動物又は有害節足動物から保護すべき作物等の植物に直接散布処理してもよく、また耕作地の土壌に生息する有害生物を防除するために、該土壌に処理してもよい。 These formulations and water dilutions of the formulations may be sprayed directly onto plants such as pest arthropods or crops that should be protected from pest arthropods, and to control pests inhabiting cultivated soil. Therefore, the soil may be treated.

また、本発明の組成物は、畑、水田、芝生、果樹園等の農耕地における有害節足動物の防除剤として使用することができる。 In addition, the composition of the present invention can be used as a control agent for harmful arthropods in agricultural lands such as fields, paddy fields, lawns and orchards.

化合物の製造例を示す。 An example of manufacturing the compound is shown.

4−クロロ−2−フルオロ−5−{[2−(エトキシカルボニル)メトキシピリジン−3−イル]オキシ}アニリン1.02g、トリエチルアミン0.35g及びクロロベンゼン3.20gの混合物に、氷冷下、トリホスゲン0.17gを加え、室温で3時間撹拌した。得られた混合物に水を加え、クロロホルムで抽出した。得られた有機層を飽和炭酸水素ナトリウム水溶液及び水で順次洗浄し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、化合物Aを0.19g得た。
1H-NMR (CDCl3) δ(ppm): 8.06-8.02 (2H, m), 7.78 (2H, dd, J = 4.9, 1.5 Hz), 7.74 (2H, d, J = 7.5 Hz), 7.08 (2H, d, J = 10.4 Hz), 6.87 (2H, dd, J = 7.8, 1.5 Hz), 6.79 (2H, dd, J = 7.8, 4.9 Hz), 5.01 (4H, s), 4.29 (4H, q, J = 7.1 Hz), 1.29 (6H, t, J = 7.1 Hz).
4-Chloro-2-fluoro-5-{[2- (ethoxycarbonyl) methoxypyridin-3-yl] oxy} aniline 1.02 g, triethylamine 0.35 g and chlorobenzene 3.20 g in a mixture under ice-cooling, triphosgene 0.17 g was added, and the mixture was stirred at room temperature for 3 hours. Water was added to the obtained mixture, and the mixture was extracted with chloroform. The obtained organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and water, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.19 g of Compound A.
1 1 H-NMR (CDCl 3 ) δ (ppm): 8.06-8.02 (2H, m), 7.78 (2H, dd, J = 4.9, 1.5 Hz), 7.74 (2H, d, J = 7.5 Hz), 7.08 ( 2H, d, J = 10.4 Hz), 6.87 (2H, dd, J = 7.8, 1.5 Hz), 6.79 (2H, dd, J = 7.8, 4.9 Hz), 5.01 (4H, s), 4.29 (4H, q) , J = 7.1 Hz), 1.29 (6H, t, J = 7.1 Hz).

次に化合物の製剤例を示す。なお、部は重量部を表す。 Next, a formulation example of the compound is shown. The part represents a weight part.

製剤例1
10部の化合物Aを、キシレン35部とDMF35部との混合物に混合し、そこにポリオキシエチレンスチリルフェニルエーテル14部及びドデシルベンゼンスルホン酸カルシウム6部を加え、混合して製剤を得る。
Formulation Example 1
10 parts of compound A is mixed with 35 parts of xylene and 35 parts of DMF, 14 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added thereto, and the mixture is mixed to obtain a preparation.

製剤例2
ラウリル硫酸ナトリウム4部、リグニンスルホン酸カルシウム2部、湿式シリカ20部及び珪藻土54部を混合し、更に20部の化合物Aを加え、混合して製剤を得る。
Formulation Example 2
4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of wet silica and 54 parts of diatomaceous earth are mixed, and 20 parts of compound A is further added and mixed to obtain a preparation.

製剤例3
2部の化合物Aに、湿式シリカ1部、リグニンスルホン酸カルシウム2部、ベントナイト30部及びカオリンクレー65部を加え混合する。ついで、この混合物に適当量の水を加え、さらに撹拌し、造粒機で造粒し、通風乾燥して製剤を得る。
Formulation Example 3
To 2 parts of compound A, 1 part of wet silica, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are added and mixed. Then, an appropriate amount of water is added to this mixture, the mixture is further stirred, granulated by a granulator, and air-dried to obtain a preparation.

製剤例4
1部の化合物Aを適当量のアセトンに混合し、これに湿式シリカ5部、酸性リン酸イソプロピル0.3部及びカオリンクレー93.7部を加え、充分撹拌混合し、アセトンを蒸発除去して製剤を得る。
Formulation Example 4
1 part of Compound A is mixed with an appropriate amount of acetone, 5 parts of wet silica, 0.3 part of acidic isopropyl phosphate and 93.7 parts of kaolin clay are added thereto, and the mixture is sufficiently stirred and mixed to evaporate and remove acetone. Get the formulation.

製剤例5
ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩及び湿式シリカの混合物(重量比1:1)35部と、化合物A20部と、水45部とを十分に混合し、製剤を得る。
Formulation Example 5
A preparation is obtained by thoroughly mixing 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and wet silica (weight ratio 1: 1), 20 parts of compound A, and 45 parts of water.

次に、化合物Aの有害節足動物に対する効力を試験例により示す。下記試験例において、試験は25℃で行った。 Next, the efficacy of Compound A on harmful arthropods will be shown by Test Examples. In the following test example, the test was performed at 25 ° C.

試験例1
化合物Aを製剤例5に記載の方法に準じて製剤とし、これに展着剤0.03容量%含有する水を加え、化合物Aを500ppm含有する希釈液を得た。
容器に植えたキュウリ(Cucumis sativus)苗(第2本葉展開期)にワタアブラムシ(全ステージ)約30頭を接種した。1日後、この苗に該希釈液を10mL/苗の割合で散布した。更に5日後、生存虫数を調査し、以下の式により防除価を求めた。
防除価(%)={1−(Cb×Tai)/(Cai×Tb)}×100
なお、式中の文字は以下の意味を表す。
Cb:無処理区の供試虫数
Cai:無処理区の調査時の生存虫数
Tb:処理区の供試虫数
Tai:処理区の調査時の生存虫数
ここで無処理区とは、化合物Aを使用しないこと以外は処理区と同じ操作をした区を意味する。
その結果、化合物Aの処理区は防除価90%以上であった。
Test Example 1
Compound A was prepared according to the method described in Formulation Example 5, and water containing 0.03% by volume of the spreading agent was added thereto to obtain a diluted solution containing 500 ppm of Compound A.
About 30 cotton aphids (all stages) were inoculated into the cucumber (Cucumis sativus) seedlings (second true leaf development stage) planted in the container. One day later, the seedlings were sprayed with the diluent at a ratio of 10 mL / seedling. After another 5 days, the number of surviving insects was investigated, and the control value was calculated by the following formula.
Control value (%) = {1- (Cb x Tai) / (Cai x Tb)} x 100
The characters in the formula have the following meanings.
Cb: Number of test insects in the untreated plot Cai: Number of surviving insects in the untreated plot Tb: Number of test insects in the treated plot Tai: Number of surviving insects in the treated plot It means a section in which the same operation as the treatment section is performed except that compound A is not used.
As a result, the treatment group of compound A had a control value of 90% or more.

化合物Aは、有害節足動物に対して優れた防除効果を示す。 Compound A exhibits an excellent control effect on harmful arthropods.

Claims (3)

式(1)
Figure 2020152642
で示される化合物。
Equation (1)
Figure 2020152642
The compound indicated by.
請求項1に記載の化合物と、不活性担体とを含有する組成物。 A composition containing the compound according to claim 1 and an inert carrier. 請求項1に記載の化合物の有効量を有害生物又は有害生物の生息場所に施用する有害生物の防除方法。 A method for controlling a pest or a pest by applying an effective amount of the compound according to claim 1 to a pest or a habitat of the pest.
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