Substituted biphenyl oxazoline derivative and method for controlling pests using same

Abstract

[Problem] To provide a new compound having a sufficient effect on pests which have developed resistance and are difficult to control and on which a known compound does not exhibit any effects. [Solution] A substituted biphenyl oxazoline derivative represented by formula (1). [In the formula: R1 represents a C1-C6 perfluoroalkyl group in which one fluorine atom is unsubstituted or substituted with a hydrogen atom or a C1-C6 alkoxy group; R2 represents a halogen atom, a C1-C6 alkoxy group, a trifluoromethyl group, or a trifluoromethanesulfonyloxy group; and X represents a fluorine atom or a chlorine atom.]

Description

Substituted biphenyloxazoline derivatives and methods for controlling their pests

[0001] This invention relates to substituted biphenyloxazoline derivatives and the use of these compounds as pest control agents.

[0002] Pesticides are useful materials for protecting crops from diseases and pests, and for reducing labor in farming and improving agricultural productivity. Among these pesticides, compounds with an oxazoline ring structure have been studied and put into practical use for the purpose of controlling harmful organisms. For example, the disclosures in Patent Documents 1 to 13 are relevant. On the other hand, reports on the development of insecticide resistance in harmful organisms are continuously increasing. For example, thrips are known as difficult-to-control pests, and many populations that have developed further resistance to pesticides have been reported. Therefore, in agriculture, there is a constant need for the development of pesticides that are highly effective against resistant pests that existing pesticides are ineffective against. Although several oxazoline derivative compounds have been disclosed with the aim of being effective against resistant pests, their effectiveness against current resistant pests is not sufficient. In agriculture, there is a constant need for novel compounds that are highly effective against pests resistant to existing pesticides.

[0003] JP-A-3-232867, JP-A-6-048907, JP-A-7-330518, Special Publication No. 10-512859, Special Publication No. 2001-521930, Publication No. 2004-536828, Chinese Patent CN10 2952056 Special Table of Contents No. 9-501426 Publication of Japanese Patent Application Publication No. 9-059115 Publication of Special Publication No. 2002-540194 United States Patent US6573286 Publication of Special Publication No. 2009-506084 International Publication WO 2013 / 169599

[0004] The problem that this invention aims to solve is to provide a novel compound that has sufficient effect against difficult-to-control pests that have developed resistance, to which known compounds are ineffective.

[0005] As a result of intensive studies to solve the above problems, the present inventors have newly found that a biphenyloxazoline derivative having a specific structure has a remarkable insecticidal / enmiticidal effect on individuals that have developed high resistance to multiple types of chemicals in various pests, and based on such findings, the present invention has been completed. The main aspects of the present invention are as follows. [1] Formula (1): [In the formula, ２ , ２ R represents a C1-C6 perfluoroalkyl group in which one fluorine atom is substituted with a hydrogen atom or a C1-C6 alkoxy group, or is unsubstituted, ２ R represents a halogen atom, a C1-C6 alkoxy group, a trifluoromethyl group or a trifluoromethanesulfonyloxy group, ２ X represents a fluorine atom or a chlorine atom. ] A substituted biphenyloxazoline derivative represented by the formula. [2] The compound according to [1], wherein X is a fluorine atom. [3] The compound according to any one of [1] to [*2], wherein R ２ is a halogen atom or a C1-C4 alkoxy group. [5] The compound according to [1], wherein R<00,00005> is a fluorine atom, a chlorine atom or a C1-C4 alkoxy group. [6] The compound according to [1], wherein R ２ is a C1-C4 alkoxy group. [7] The compound according to [1], wherein R ２ is a halogen atom. [8] The compound according to [1], wherein R ２ is a fluorine atom or a chlorine atom. [9] The compound according to [1], wherein R １ is a C1-C6 perfluoroalkyl group.

[10] The compound according to [1], wherein R １ is a C1-C4 perfluoroalkyl group in which one fluorine atom is substituted with a hydrogen atom or a methoxy group, or is unsubstituted.

[11] The compound according to [9], wherein R １ is a C1-C4 perfluoroalkyl group.

[12] R<000001*2>The compound according to

[10] , wherein one fluorine atom is substituted with a hydrogen atom or a methoxy group, or is an unsubstituted C3-C4 perfluoroalkyl group.

[13] R １ The compound according to

[11] , wherein the compound is a C3-C4 perfluoroalkyl group.

[14] A pest control agent containing the compound according to any one of [1] to

[13] and an auxiliary agent.

[15] A method for controlling pests by applying an effective amount of the compound according to any one of [1] to

[13] .

[16] The method according to

[15] , comprising applying an effective amount of the compound according to any one of [1] to

[13] to a pest or a plant inhabited by a pest or soil in which the plant is cultivated.

[0006] The compounds of the present invention have excellent control activity against harmful organisms. These compounds also exhibit excellent control activity against highly resistant and difficult-to-control harmful organisms that cannot be controlled by known compounds.

[0007] In this specification, expressions such as "Ca to Cb" preceding each substituent mean that the corresponding group contains a to b carbon atoms. "Halogen atoms" include fluorine, chlorine, bromine, and iodine atoms. "Alkyl" as used in the group itself or in part of the group can be linear or branched, and is not limited to these, but examples include methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n-pentyl, and n-hexyl, each selected within the specified range of carbon atoms. "Perfluoroalkyl" means that the alkyl portion has the meaning described above, and all hydrogen atoms bonded to carbon atoms are replaced by fluorine atoms. Examples include trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-iso-propyl, nonafluoro-n-butyl, nonafluoro-iso-butyl, nonafluoro-sec-butyl, nonafluoro-tert-butyl, undecafluoro-n-pentyl, and tridecafluoro-n-hexyl, each selected within the specified range of carbon atoms. "Alkoxy" means an alkyl-O- group where the alkyl portion has the meaning described above. Examples include methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy, n-pentyloxy, and n-hexyloxy, each selected within the specified range of carbon atoms.

[0008] The compounds of formula (I) included in the present invention have optically active forms due to the presence of one or more chiral carbon atoms, but the present invention includes all optically active forms or racemic mixtures.

[0009] In a compound of formula (I) encompassed by the present invention, R １Substituents represented by include C1-C6 perfluoroalkyl groups in which one fluorine atom is substituted with a hydrogen atom or a C1-C6 alkoxy group, or is unsubstituted. Of these, C1-C4 perfluoroalkyl groups in which one fluorine atom is substituted with a hydrogen atom or a methoxy group, or is unsubstituted, are preferred, C3-C4 perfluoroalkyl groups in which one fluorine atom is substituted with a hydrogen atom or a methoxy group, or is unsubstituted, are more preferred, and C3-C4 perfluoroalkyl groups are particularly preferred. In the compound of formula (I) encompassed by the present invention, R ２ Substituents represented by include halogen atoms, C1-C6 alkoxy groups, trifluoromethyl groups, or trifluoromethanesulfonyloxy groups, of which fluorine atoms, chlorine atoms, or C1-C4 alkoxy groups are preferred, and fluorine atoms or chlorine atoms are particularly preferred. In the compounds encompassed by the present invention, substituents represented by X include fluorine atoms or chlorine atoms, of which fluorine atoms are preferred. Compounds of formula (I) encompassed by the present invention include R １ The substituent represented by is a C1-C6 perfluoroalkyl group in which one fluorine atom is substituted with a hydrogen atom or a C1-C6 alkoxy group, or is unsubstituted. ２ Examples of compounds in which the substituent represented by is a halogen atom, a C1-C6 alkoxy group, a trifluoromethyl group, or a trifluoromethanesulfonyloxy group, and the substituent represented by X is a fluorine atom or a chlorine atom, among these, R １ The substituent represented by is a C1-C4 perfluoroalkyl group in which one fluorine atom is substituted with a hydrogen atom or a methoxy group, or is unsubstituted, and R ２ A compound in which the substituent represented by is a fluorine atom, a chlorine atom, or a C1-C4 alkoxy group, and the substituent represented by X is a fluorine atom, is preferred. １ The substituent represented by is a C3-C4 perfluoroalkyl group in which one fluorine atom is substituted with a hydrogen atom or a methoxy group, or is unsubstituted, and R ２Compounds in which the substituent represented by is a fluorine atom or a chlorine atom, and the substituent represented by X is a fluorine atom, are more preferably R １ The substituent represented is a C3-C4 perfluoroalkyl group, and R ２ Compounds in which the substituent represented by is a fluorine atom or a chlorine atom, and the substituent represented by X is a fluorine atom, are particularly preferred.

[0010] Next, a method for producing the compound of the present invention will be described.

[0011] The compounds of the present invention can be produced, for example, by the following manufacturing method.

[0012] In all of the following formulas, substituents and symbols have the same meanings as defined above for formula (1), unless otherwise defined.

[0013] <Method for producing biphenyloxazoline derivative (1)> The compound of formula (1) provided by the present invention can be produced by either method (A1) or (A2).

[0014] Method (A1): A method for producing the compound of formula (1), characterized by cyclizing a benzamide derivative represented by formula (2) in the presence of a base to obtain an oxazoline derivative of formula (3), and then carrying out a Suzuki-Miyaura coupling reaction with a substituted phenylboronic acid (4) or its pinacol ester (5). This reaction can be carried out by referring to known reaction conditions (see, for example, Japanese Patent Publication No. 11-513663, Chem. Rev. 1995, 95, 2457-2483, and US20110071150). (In the formula, Y represents a bromine atom or an iodine atom, and L represents a chlorine atom or a methanesulfonyloxy group.)

[0015] Method (A2): A method for producing the compound of formula (1), characterized by reacting a substituted biphenyl represented by formula (6) with a benzamide derivative represented by formula (7) in the presence of an acid to produce the compound of formula (8), and then cyclizing the compound in the presence of a base. This reaction can be carried out by referring to known reaction conditions (for example, see Russ. J. Org. Chem. 2003, 39(12), 1753-1759, Japanese Patent Publication No. 11-513663). (In the formula, L represents a chlorine atom.)

[0016] The compound of formula (6) used as a starting material in method (A2) is commercially available or can be easily produced by known methods such as the Suzuki-Miyaura coupling reaction between a substituted halogenobenzene and a substituted phenylboronic acid. The other starting material, compound of formula (7), can be easily produced by known methods described in the literature (for example, Japanese Patent Application Publication No. 6-135916) and the literature cited therein.

[0017] <Method for producing benzamide derivative (2)> The benzamide derivative of formula (2) used as a starting material in method (A1) can be produced by any of the following methods (B1), (B2), or (B3).

[0018] Method (B1): A method for producing the compound of formula (2), characterized by reacting a commercially available substituted phenol represented by formula (9) with a benzamide derivative represented by formula (7) in the presence of an acid to produce an intermediate of formula (10), and further etherifying or trifluoromethanesulfonyling the hydroxyl group in the presence of a base. This reaction can be carried out by referring to known reaction conditions (see, for example, Japanese Patent Publication No. 11-513663, Synthesis, 2005, (4), 547-550). (In the formula, L represents a chlorine atom, and R ２ (This represents a C1-C6 alkoxy group or a trifluoromethanesulfonyloxy group.)

[0019] Method (B2): A method for producing the compound of formula (2), characterized by reducing the oxime ester derivative shown in formula (11) to the amino alcohol derivative of formula (12), then reacting it with a commercially available substituted benzoyl chloride shown in formula (13) in the presence of a base to produce the amide alcohol compound of formula (14), and further reacting it with methanesulfonyl chloride. This reaction can be carried out by referring to known reaction conditions (for example, see Japanese Patent Publication No. 11-513663, WO9741091). (In the formula, R ３(where represents a methyl or ethyl group, and L represents a methanesulfonyloxy group.)

[0020] Method (B3): A method for producing the compound of formula (2), characterized by first converting a commercially available substituted benzaldehyde represented by formula (15) into an epoxide of formula (16), then reacting it with sodium azide to produce an azide alcohol of formula (17), and then reacting it with an amino alcohol of formula (12) produced by a Staudinger reaction in the same manner as in method (B2). This reaction can be carried out by referring to known reaction conditions (see, for example, Tetrahedron, 2009, 65(39), 8199-8205, J. Org. Chem. 2008, 73(6), 2270-2274). (In the formula, L represents a methanesulfonyloxy group.)

[0021] <Method for producing oxime ester derivative (11)> The oxime ester derivative of formula (11) used as a starting material in method (B2) can be produced by any of the following methods (C1), (C2), or (C3).

[0022] Method (C1): A method for producing the compound of formula (11), characterized by reacting a commercially available substituted benzene represented by formula (18) with a chloroglyoxylate ester in the presence of a Lewis acid to obtain the ketoester of formula (19), and then reacting it with hydroxylamine hydrochloride. This reaction can be carried out by referring to known reaction conditions (for example, see Japanese Patent Publication No. 11-513663).

[0023] Method (C2): A method for producing the compound of formula (11), characterized by alkylating a commercially available substituted phenylacetic acid represented by the following formula (20) to obtain the ester of formula (21), and then reacting it with a nitrite ester in the presence of a base. This reaction can be carried out by referring to known reaction conditions (see, for example, Japanese Patent Publication No. 11-513663 and Japanese Patent Publication No. 2008-524333).

[0024] Production method (C3): A commercially available substituted aniline represented by the following formula (22) is iodinated by the Sandmeyer reaction to obtain formula (23), an aryl Grignard reagent is prepared and reacted with chloroglyoxylic acid ester to obtain a ketoester form of formula (21), and then it is reacted with hydroxylamine hydrochloride in the same manner as in production method (C1). A method for producing a compound of formula (11), characterized by reacting the compound with hydroxylamine hydrochloride. This reaction can be carried out by referring to reaction conditions known per se (for example, see Chem. Rev. 1947, 40, 251-@ -277, WO2007034282, Org. Chem. Front. 2018, 5(18), 2723-2727). (In the formula, Y represents a bromine atom.)

[0025] <Production method of phenylboronic acid (4) and phenylboronic acid pinacol ester (5)> The compounds of formula (4) and formula (5) used in production method (A1) are commercially available or can be produced from the substituted aniline shown in formula (24) via a substituted halogenobenzene (25) or directly from the substituted aniline (24) by known methods described in the literature (for example, Angew. Chem., Int. Ed. 2010, 49(10), 1846-1849, J. Org. Chem. 1995, 60, 7508-7510, Org. Lett. 2011, 13(17), 4479-4481) and the literature cited therein.

[0026] <Production method of substituted aniline (24)> The substituted aniline of formula (24) can be produced by any of the following production methods (D1), (D2), or by production method (D3) after any of production methods (D1), (D2).

[0027] Production method D1: A method for producing a compound of formula (24), characterized by reacting aniline with perfluoroalkyl iodide This reaction can be carried out by referring to reaction conditions known per se (for example, see EP1006102).

[0028] Production Method D2: A method for producing a compound of formula (24), characterized by reacting 4-iodoaniline with a perfluoroalkyl iodide in the presence of a copper catalyst. The reaction can be carried out by referring to reaction conditions known per se (see, for example, New J. Chem. 2013, 37(12), 4140 - 4147).

[0029] Production Method D3: When R in formula (4) or formula (5) is a perfluoroalkyl group in which one fluorine atom is substituted with a hydrogen atom or a C1 - C6 alkoxy group, after carrying out either of Production Methods (D1) and (D2), a reduction reaction or a reaction with sodium alkoxide is carried out. A method for producing a compound of formula (24), characterized by this. The reaction can be carried out by referring to reaction conditions known per se (see, for example, WO2002094765, WO2008099820). １

[0030] Pests against which the compound of the present invention and the pest control agent of the present invention have a control effect include, for example, pests such as harmful insects and harmful mites. Specific examples of such pests include the following.

[0031] ​Pests of the order Hemiptera: Planthoppers such as Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, and Peregrinus maidis; leafhoppers such as Nephotettix cincticeps, Nephotettix virescens, Rice green leafhopper (Nephotettix nigropictus), Recilia dorsalis, and Empoasca Leafhoppers such as onukii, potato leaf hopper (Empoasca fabae), corn leaf hopper (Dalbulus maidis), sugarcane froghopper (Mahanarva posticata), sugarcane root spittles (Mahanarva fimbriota), white leafhopper (Cofana spectra), black-striped leafhopper (Nephotettix nigropictus), cotton aphid (Aphis gossypii), peach aphid (Myzus persicae), and radish aphid (Brevicoryne) Brassicae, Spiraea aphid (Aphis spiraecola), Tulip aphid (Macrosiphum euphorbiae), Potato aphid (Aulacorthum solani), Wheat aphid (Rhopalosiphum padi), Citrus aphid (Toxoptera citricidus), Peach aphid (Hyalopterus pruni), Soybean aphid (Aphis gycynes matsumura), Corn aphid (Rhopalosiphum maidis), Rhopalosiphum tetraneura nigriabdominalis), grape aphid (Viteus v. jpgoliae), Grape Phylloxera (Daktulosphaira v. jpgoliae),Aphids such as Pecan phylloxera (Phylloxera devastatrix Pergande), Pecan leaf phylloxera (Phylloxera notabilis Pergande), Southern pecan leaf phylloxera (Phylloxera russellae Stoetzel), rice black bug (Scotinophara lurida), Malayan rice black bug (Scotinophara coarctata), and green stink bug (Nezara) antennata), Eysarcoris parvus, Halyomorpha mista, Nezara viridula, Brown stink bug (Euschistus heroes), Southern green stink bug (Nezara viridula), Red banded stink bug (Piezodorus guildinii), Burrower brown bug (Scaptocoris castanea), Oebalus pugnax, Dichelops Stink bugs such as Melacanthus, Reptortus clavetus, Leptocorisa chinensis, Leptocorisa acuta, Leptocorisa species, Trigonotylus caelestialium, Stenotus rubrovittatus, Lygus lineararius, and Chinchi bug (Blissus leucopterus) Miridae such as Leucopterus, greenhouse whiteflies (Trialeurodes vaporariorum), tobacco whiteflies (Bemisia tabaci), citrus whiteflies (Dialeurodes citri), citrus spiny whiteflies (Aleurocanthus spiniferus), and other whiteflies.Red scale insect (Aonidilla aurantii), San Jose scale insect (Comstoccaspis perniciosa), Citrus snow scale insect (Unaspis citri), Ruby scale insect (Ceroplastes rubens), Icerya scale insect (Icerya purchasi), Fuji scale insect (Planococcus kraunhiae), Mulberry scale insect (Pseudaucoccus longispinis), Mulberry white scale insect (Pseudaulacaspis pentagona), Tuttlemee bug (Brevennia) Scale insects such as *rehi*, psyllids such as *Diaphorina citri*, *Psylla pyrisuga*, and *Bactericerca cockerelli*, lace bugs such as *Stephanitis nasi*, bed bugs such as *Cimex lectularius*, and giant cicada (Quesada gigas).

[0032] Lepidopteran pests: Chilo suppressalis, Darkheaded stem bore (Chillo polychrysus), Triporyza incertulas, Tropical stem borer (Chillo polychrysus), White stem borer (Scirpophaga innotata), Yellow stem bore (Scirpophaga incertulas), Pink bore (Sesamia inferens), Rupela albinella, Rumex rotundifolius (Cnaphalocrocis medinalis), Marasmia Patnalis, Marasmia exigna, Cotton borer (Notarcha derogata), Indian meal moth (Plodia interpunctella), Corn borer (Ostrinia furnacalis), Diamondback moth (Hellula undalis), Sod web moth (Pediasia teterrellus), Rice case worm (Nymphula depunctalis), Marasmia genus, Hop vine bore (Hydraecia immanis), European corn bore (Ostrinia nubilalis), Lesser cornstalk Moths such as bore (Elasmopalpus lignosellus), Bean Shoot Borer (Epinotia aporema), Sugarcane Borer (Diatraea saccharalis), Giant Sugarcane Borer (Telchin licus), beet armyworm (Spodoptera litura), white-striped armyworm (Spodoptera exigua), foxtail armyworm (Pseudaletia separata), cutworm (Mamestrata brassicae), and rice armyworm (Sesamia) inferens), Spodoptera mauritia, Spodoptera frugiperda, Spodoptera exceptta, Agrotis ipsilon,Plusia nigrisigna, Soybean looper (Pseudoplusia includens), Trichoprusia, Heliothys virescences and other Heliothys species, Helicoverpa armigera and other Helicoverpa species, Velvetbean caterpillar (Anticarsia gammatalis), Cotton leafworm (Alabama argillacea) and other noctuid moths, Pieris rapae and other white butterflies, Adoxophies species, Pear leaf moth (Grapholita) Tortricidal moths such as molesta, bean pod moth (Leguminivora gycinivorella), adzuki bean pod moth (Matsumuraeses azukivora), apple tortrix moth (Adoxophyes orana fasciata), tea tortrix moth (Adoxophyes honmai.), tea tortrix moth (Homona magnanima), variegated tortrix moth (Archips fuscocupreanus), codling moth (Cydia pomonella), tea leaf roller moth (Caloptilia theivora), golden leaf roller moth (Phyllonorecter) Narrow-legged moths such as ringoneella, fruit moths such as Carposina niponensis and Citrus fruit bore (Ecdytolopha aurantiana), leaf miners such as coffee leaf miner (Leucoptera coffeela) and Lyonetia, poisonous moths such as Limantria and Euplocthys, diamondback moths such as Plutella xylostella, cotton beetles such as Pectinophora gossypierla and potato moth (Phyromaea operculella), and fall webworms (Hyphantria) Tribatid species such as *Cunea*.

[0033] Thrips pests: Thrips species such as the citrus yellow thrips (Frankliniella occidentalis), southern yellow thrips (Thrips parmi), tea yellow thrips (Scirtothrips dorsalis), onion thrips (Thrips tabaci), flat-headed flower thrips (Frankliniella intonsa), Western flower thrips (Frankliniella occidentalis), rice thrips (Haplothrips aculeatus), and rice thrips (Stenchaetothrips biformis).Diptera pests: Culex pipiens pallens, Culex tritaeniorhynchus, Culex quinquefasciatus and other house mosquitoes; Aedes species such as Aedes aegypti and Aedes albopictus; Anopheles species such as Anopheles sinensis; midges; houseflies such as Musca domestica and Muscina stabulans; seed flies (Delia platura), onion flies (Delia Flower flies such as *Antiqua*, sugar beetroot maggot (Tetanops myopaeformis), leafminers such as rice leafminer (Agromyza oryzae), rice leafminer (Hydrellia griseola), tomato leafminer (Liriomyza sativae), bean leafminer (Liriomyza trifolii), and leafminer (Chromatomyia horticola), leafminers such as rice leafminer (Chlorops oryzae), melon flies (Dacus cucurbitae), Mediterranean fruit flies (Ceratitis) Fruit flies such as *Capitata*, shore flies such as *Hydrellia philippina* and *Hydrellia sasakii*, fruit flies, phorid flies such as *Megaselia spiracularis*, drain flies such as *Clogmia albipunctata*, fungus gnats, gall midges such as *Mayetiola destroyer* and *Orseolia oryzae*, hammerhead flies such as *Diopsis macrophthalma*, Common Crane flies such as the common crane fly (Tipula oleracea) and the European crane fly (Tipula paludosa).

[0034] Coleopteran pests: 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 LeConte), San Antonio beetle (Diabrotica speciosa), Cucurbit beetle (Diabrotica speciosa), Bean leaf beetle (Cerotoma) trifurcata, cereal leaf beetle (Oulema melanopus), cucumber beetle (Aulacophora femoralis), striped flea beetle (Phyllotreta striolata), Colorado leaf beetle (Leptinotarsa ​​decemlineata), rice leaf beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn flare beetle (Chaetocnema pulicalia), potato flare beetle (Epitrix cucumeris), rice spine beetle (Dicladispa armigera), seedcorn beetle (Stenolophus) Leaf beetles such as *lecontei*, Slender seedcorn beetle (Clivinia impressifrons), Japanese beetle (Anomala cuprea), Japanese dung beetle (Anomala rufocuprea), Japanese beetle (Popillia japonica), European chafer (Rhizotrogus majalis), carrot beetle (Bothynus gibbosus), Grape Colaspis (Colaspis brunnea), southern corn leaf beetle (Myochrous) Scarab beetles such as *Denticollis*, *Holotricia*, and *Phyllophaga* species including the June beetle (*Phyllophaga crinita*),Rice weevils such as Sitophilus zeamais, Echinocnemus squameus, Lissorhoptrus oryzophilus, and Sphenophorus venatus, as well as cotton weevils (Anthonomus grandis), Southern Corn Billbug (Sphenophorus callosus), Soybean stick weevil (Sternechus subsignatus), and Sphenophorus Weevils such as Levis and other species of the genus Sphenophorus, Epilachna species such as the 28-spotted ladybug (Epilachna vigintioctopunctata), bark beetles such as Lyctus brunneus and Tomicus piniperda, longhorn beetles, leaf beetles, longhorn beetles such as Anoplophora malasiaca and Migdolus fryanus, Okinawa click beetles (Melanotus okinawensis) and brown-brown click beetles (Agriotes ogurae) Click beetles such as *Fuscicollis*, *Melanotus legatus*, *Agriotes sp.*, *Aelous sp.*, *Anchastus sp.*, *Melanotus sp.*, *Limonius sp.*, *Conoderus sp.*, *Ctenicera sp.*, *Paederus fuscipes*, and other rove beetles, as well as the Coffee Barry Borer (Hypothenemus hampei).

[0035] Grasshopper pests: Migratory locust (Locusta migratoria), mole cricket (Gryllotalpa africana), Moroccan grasshopper (Dociostaurus maroccanus), Australian grasshopper (Chortoicetes terminifera), Red grasshopper (Nomadacris septemfasciata), Brown grasshopper (Locusta na pardalina), Tree grasshopper (Anacridium melanorhodon), Italian grasshopper (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Twostripped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus femurrubrum), Clearwinged grasshopper (Camnula Yellow-winged locust (Gastrimargus), Yellow-winged locust (Schistocerca gregaria), Crickets such as *musicus*, *Spur-throated locust* (Austracris guttulosa), *Oxya yezoensis*, *Oxya japonica*, *Patanga succincta*, *Acheta domesticus*, and *Teleogryllus emma*, *Anabrus simplex*, and other types of crickets. Hymenoptera pests: Sawflies such as the cabbage sawfly (Athalia rosae) and the Japanese cabbage wasp (Athalia japonica), fire ants, and leafcutter ants such as the brown leaf-cutting ant (Atta capiguara).

[0036] Cockroach pests: German cockroach (Blattella germanica), Oriental cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta amelicana), Brown cockroach (Periplaneta brunnea), Eastern cockroach (Blatta orientalis). Termite pests: Japanese subterranean termite (Reticulitemes speratus), Formosanus subterranean termite (Coptotermes formosanaus), Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanaus, Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, and Coptotermes species. fuscus), Kodama termite (Glyptotermes kodamai), Kushimoto termite (Glyptotermes kushimensis), Large termite (Hodotermopsis sjostedti), Koshu termite (Coptotermes guangzhoensis), Amami termite (Reticulitermes amamianus), Miyatake termite (Reticulitermes miyatakei), Kanmon termite (Reticulitermes kanmonensis.), Takasago termite (Nasutitermes takasagoensis), Nitobe termite (Pericapritermes) Examples include *Cornite nitobei*, *Sinocapritermes mushae*, and *Cornitermes cumulans*.

[0037] Acari pests: Spider mites such as Tetranychus urticae, Tetranychus kanzawai, Panonychus citri, Panonychus ulmi, Oligonicus species and Southern Turkey spider mites (Brevipalpus phoenicis), citrus rust mite (Aculops pelekassi), Ryukyu citrus rust mite (Phyllocoptruta citri), tomato rust mite (Aculops lycopersici), and tea rust mite (Calacarus) Gall mites such as *Carinatus*, *Acapylella theavagrans*, *Eriophyes chibaensis*, and *Aculus schlechtendali*; dust mites such as *Polyphagotarsonemus latus*; small spider mites such as *Brevipalpus phoenicis*; long-haired spider mites; *Haemaphysalis longicornis*, *Haemaphysalis flava*, and *Dermacenter*. Ticks such as *Ixodes taiwanicus*, *Dermacenter variabilis*, *Ixodes ovatus*, *Ixodes persulcatus*, *Ixodes scapularis*, *Amblyoma americanum*, *Boophilus microplus*, *Rhipicephalus sanguineus*, *Tyrophagus putrescentiae*, and *Tyrophagus* Dust mites such as *Dermatophthosis similis*, house dust mites such as *Dermatophthosis farinae* and *Dermatophthosis ptrenyssnus*,Cheyletus eruditus, Cheyletus malaccensis, Cheyletus morei, Cheyletiella yasguri, and other Cheyletiella mites; Octodectes cynotis, Sarcoptes scabiei, and other Sarcoptes scabiei mites; Demodex canis and other Demodex mites; Head mites; Oribatid mites; House mites (Ornithonyssus bacoti), and Bird mites (Ornithonyssus) Mice such as *Sylvairum*, *Dermanyssus gallinae*, and other types of mite mite species, and scrub mites such as *Leptotrombidium akamushi*. Spiders: *Chiracanthium japonicum*, *Latrodectus hasseltii*, etc. Chilopoda: *Thereuonema hilgendorfi*, *Scolopendra subsp. nipes*, etc. Diplopoda: Millipedes (Oxidus gracilis), Millipedes (Nedyopus tambanus), etc. Isopoda: Pill bugs (Armadillidium vulgare), etc. Gastropoda: Brown slugs (Limax marginatus), Yellow slugs (Limax flavus), Apple snails (Pomacea canaliculata), etc.

[0038] Examples of harmful nematodes include the following:

[0039] Harmful nematodes: Aphelenchoides sp. such as rice stem nematode (Aphelenchoides basseyi), root-knot nematodes such as southern root-knot nematode (Pratilenchus coffeae), Pratylenchus brachyurus, wheat root-knot nematode (Pratilenchus negregtus), Javan root-knot nematode (Meloidogyne javanica), sweet potato root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne) Root-knot nematodes such as Meloidogyne sp. (hapla), Heterodera sp. (soybean cyst nematodes such as Heterodera gycynes), Globodera sp. (potato cyst nematodes such as Globodera rostochiensis), Rotylenchulus reniformis, Strawberry nematode (Nottylenchus acris), Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans This includes species such as semipenetrans, Longidorus sp., Xiphinema sp., Trichodorus sp., and Bursaphelenchus sp., including the pine wood nematode (Bursaphelenchus xylophilus).

[0040] The compound of formula (1) of the present invention can be used alone, but it is usually preferable to formulate it into any dosage form, such as powder, emulsion, oil, solubilizer, sposomal emulsion, fine granules, spray, DL powder, fine granules F, fine granules F, granules, wettable powder, granular wettable powder, flowable powder, tablet, paste, oily suspension, water-soluble powder, granular water-soluble powder, liquid, microcapsule, etc., according to conventional methods. The pest control agent of the present invention usually contains 0.01 to 95% by weight of the compound of the present invention.

[0041] Potential additives that can be used in formulation include, but are not limited to, solid carriers, liquid carriers, binders, thickeners, surfactants, antifreezes, preservatives, and defoamers.

[0042] The solid carriers used in formulation are not limited to talc, but examples include talc, bentonite, montmorillonite, clay, kaolin, calcium carbonate, sodium carbonate, baking soda, Glauber's salt, zeolite, starch, acid clay, diatomaceous earth, white carbon, vermiculite, slaked lime, vegetable powder, alumina, activated carbon, sugars, hollow glass, silica sand, ammonium sulfate, and urea.

[0043] The liquid carriers used in formulation are not limited to these, but examples include hydrocarbons (kerosene, mineral oil, etc.), aromatic hydrocarbons (toluene, xylene, dimethylnaphthalene, phenylxylethane, etc.), halogenated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters (ethyl acetate, ethylene glycol acetate, dibutyl maleate, etc.), alcohols (methanol, n-hexanol, ethylene glycol, etc.), acid amides (DMF, dimethylacetamide, etc.), sulfoxides (DMSO, etc.), propylene carbonate, and vegetable oils (soybean oil, cottonseed oil, etc.), and water.

[0044] The surfactants are not limited to these, but examples include fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkylaryl sulfates, alkyl diglycol ether sulfates, alcohol sulfates, alkyl sulfonates, alkylaryl sulfonates, aryl sulfonates, lignin sulfonates, alkyl diphenyl ether disulfonates, polystyrene sulfonates, alkyl phosphates, alkylaryl phosphates, styrylaryl phosphates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylaryl ether sulfates, and polyoxyethylene alkyl ether phosphates. Examples include anionic surfactants such as polyoxyethylene alkylaryl phosphate salts and naphthalene sulfonic acid formalin condensate salts, and nonionic surfactants such as sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides, fatty acid alcohol polyglycol ethers, acetylene glycol, acetylene alcohol, oxyalkylene block polymers, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylaryl ethers, polyoxyethylene glycol alkyl ethers, polyoxyethylene fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene hydrogenated castor oil, and polyoxypropylene fatty acid esters.

[0045] Examples of binders and thickeners, though not limited to them, include dextrin, pregelatinized starch, sodium salt of carboxymethylcellulose, polycarboxylic acid polymers, polyvinylpyrrolidone, polyvinyl alcohol, sodium ligninsulfonate, calcium ligninsulfonate, sodium polyacrylate, gum arabic, sodium alginate, mannitol, sorbitol, bentonite-based minerals, polyacrylic acid and its derivatives, white carbon, and natural sugar derivatives (e.g., xanthan gum, guar gum, etc.).

[0046] Examples of antifreeze agents, though not limited to them, include ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0047] Examples of preservatives, though not limited to them, include benzoic acid, sodium benzoate, methyl parahydroxybenzoate, butyl parahydroxybenzoate, isopropylmethylphenol, benzalkonium chloride, chlorhexidine hydrochloride, hydrogen peroxide, chlorhexidine gluconate, salicylic acid, sodium salicylate, zinc pyrithione, sorbic acid, potassium sorbate, dehydroacetic acid, sodium dehydroacetate, phenoxyethanol, isothiazolin derivatives such as 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one, 2-bromo-2-nitropropane-1,3-diol, and salicylic acid derivatives.

[0048] Examples of defoaming agents include silicone-based defoaming agents, although these are not limited to any specific type.

[0049] The solid carriers, liquid carriers, binders, thickeners, surfactants, antifreezes, preservatives, and defoamers described above can be used individually or in appropriate combinations depending on the intended use.

[0050] These formulations can be used for various purposes by diluting them to an appropriate concentration as needed and spraying them on or directly applying them to pests or their habitats (plants, soil in which plants are grown, inside houses, and animal bodies, etc.).

[0051] The dosage of the compound of formula (1) of the present invention can be varied over a wide range depending on the type of compound, the type of target plant, the time of application, the location of application, the properties of the desired effect, etc. However, as a general guideline, an example can be given of about 0.01 to 100 g, preferably about 0.1 to 10 g, of the active compound per are.

[0052] The pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention directly to the pest and / or to the habitat of the pest. Examples of habitats for pests include plants, soil in which plants are cultivated, inside houses, and animal bodies.

[0053] Methods for applying an effective amount of the compound of the present invention to plants or the soil in which plants are cultivated include, for example, applying an effective amount of the compound of the present invention to the stems and leaves, flower stalks, seedlings or ears of plants; applying an effective amount of the compound of the present invention to seeds or bulbs such as seed potatoes through seed disinfection, seed soaking, or seed coating; and applying an effective amount of the compound of the present invention to the soil before or after planting plants.

[0054] Methods for applying an effective amount of the compound of the present invention to the stems, leaves, flower stalks, seedlings, or ears of plants include, specifically, applying an effective amount of the compound of the present invention or the pest control agent of the present invention to the surface of the plant, such as by foliar spraying or trunk spraying; spraying an effective amount of the compound of the present invention onto the flower stalks or the entire plant during the flowering period, including before, during, and after flowering; and, in the case of grains, spraying an effective amount of the compound of the present invention onto the ears or the entire plant at the heading stage.

[0055] Furthermore, methods for controlling harmful organisms by applying an effective amount of the compound of the present invention to the soil before or after planting plants include, for example, a method of directly controlling harmful organisms by applying an effective amount of the compound of the present invention to the rhizosphere of crops that are to be protected from damage such as feeding by harmful organisms, or a method of controlling harmful organisms that feed on plants by allowing an effective amount of the compound of the present invention to permeate and move into the plant body from the roots or other parts.

[0056] Methods for applying an effective amount of the compound of the present invention to the soil before or after planting plants include, for example, planting hole treatment (spraying in planting holes, mixing into planting hole treatment soil), base treatment (spraying around the base of the plant, mixing into the base of the plant soil, drenching around the base of the plant, base treatment in the latter half of the seedling stage), furrow treatment (spraying in planting furrows, mixing into planting furrow soil), furrowing treatment (spraying in furrows, mixing into furrow soil, spraying in furrows during the growing season), furrowing treatment at sowing (spraying in furrows at sowing, mixing into furrows at sowing), overall treatment (spraying in the overall soil, mixing into the overall soil), side-dressing treatment, water surface treatment (application to the water surface, application to the water surface after flooding), and other soil application treatments (foliar application of granular material during the growing season, application under the tree canopy or around the main trunk, application to the soil surface, mixing into the soil surface, sowing Examples of treatments include hole application, surface application on ridges, interplant application), other drenching treatments (soil drenching, seedling stage drenching, chemical injection treatment, base drenching, chemical drip irrigation, chemigation), seedling tray treatments (seedling tray application, seedling tray drenching, seedling tray watering), seedling tray treatments (seedling tray application, seedling tray drenching, seedling tray watering), seedling bed treatments (seedling bed application, seedling bed drenching, watered seedling bed application, seedling soaking), bed soil mixing treatments (bed soil mixing, bed soil mixing before sowing, application before covering with soil at sowing, application after covering with soil at sowing, covering with soil mixing), and other treatments (growing soil mixing, tilling, topsoil mixing, soil mixing at rainwater drainage points, planting location treatment, granular flower cluster application, paste fertilizer mixing).

[0057] In the process of applying the compound to seeds or bulbs, "seeds" refers to plant seeds before sowing in soil or a growing medium, and "bulbs" refers to plant bulbs, corms, tubers, rhizomes, stem fragments, seed potatoes, or tuberous roots before planting in soil or a growing medium. Methods for controlling pests by applying an effective amount of the compound of the present invention to seeds or bulbs include, for example, a method of directly applying an effective amount of the compound of the present invention to the seeds or bulbs of a plant that you want to protect from damage such as feeding by pests to control pests; a method of applying an effective amount of the compound of the present invention near the seeds or bulbs to control pests that feed on seeds, etc.; or a method of allowing an effective amount of the compound of the present invention to permeate and move from the seeds or bulbs into the plant body to control pests that feed on plants. Methods for applying an effective amount of the compound of the present invention to seeds or bulbs include, for example, spraying, coating, dipping, impregnation, coating, film coating, and pellet coating. These methods can be used to prepare seeds or bulbs that retain an effective amount of the compound of the present invention on their surface and / or internally.

[0058] When the compound of the present invention is applied to seeds or bulbs, the effective amount of the compound of the present invention is usually 0.001 to 100 g, preferably 0.02 to 20 g, per 1 kg of seeds or bulbs.

[0059] The following are examples of plants in which the compounds and pest control agents of the present invention can be used: Agricultural crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beets, rapeseed, sunflowers, sugarcane, tobacco, etc. Vegetables: Solanaceae vegetables (eggplant, tomato, bell pepper, chili pepper, potato, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (leek, onion, garlic, asparagus), Apiaceae vegetables (carrot, parsley, celery, angelica tree, etc.), Amaranthaceae vegetables (spinach, Swiss chard, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yams, taro, etc. Fruit trees: Pome fruits (apples, European pears, Japanese pears, quince, marzipan, etc.), drupes (peaches, plums, nectarines, apricots, cherries, prunes, etc.), citrus fruits (Unshu mandarins, oranges, lemons, limes, grapefruit, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, olives, loquats, bananas, coffee, dates, coconuts, oil palms, etc.; Trees other than fruit trees: Tea, mulberry, flowering trees (azalea, camellia, hydrangea, sasanqua, Japanese star anise, cherry, tulip tree, crape myrtle, osmanthus, etc.), street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, Judas tree, sweetgum, plane tree, zelkova, Japanese cypress, fir, hemlock, juniper, pine, spruce, yew, elm, horse chestnut, etc.), coralberry, Japanese yew, cedar, cypress, croton, Japanese spindle tree, photinia, etc.;Lawns: Zoysia grasses (Zoysia japonica, Zoysia japonica, etc.), Bermuda grasses (Zoysia japonica, etc.), Bentgrasses (Poa annua, Poa arvensis, Poa crus-galli, etc.), Bluegrasses (Poa annua, Poa maximowiczii, Poa japonica, etc.), Fescues (Poa annua, Poa crus-galli, Poa japonica, etc.), Ryegrasses (Ryegrass, Ryegrass, etc.), Timothy grass, Oriental grass, etc. Others: Flowering plants (roses, carnations, chrysanthemums, lisianthus, baby's breath, gerberas, marigolds, salvias, petunias, verbenas, tulips, asters, gentians, lilies, pansies, cyclamen, orchids, lilies of the valley, lavender, stocks, ornamental cabbages, primroses, poinsettias, gladiolus, cattleyas, daisies, cymbidiums, begonias, etc.), biofuel plants (jatropha, safflower, thuja species, switchgrass, miscanthus, reeds, giant bamboo, kenaf, cassava, willow, etc.), ornamental plants, etc.

[0060] The aforementioned plants include genetically modified plants.

[0061] The present invention will be described in more detail below with reference to manufacturing examples, formulation examples, and test examples, but the present invention is not limited to these examples. <Manufacturing Examples>

[0062] Preparation Example 1 - 1. Method of preparing ethyl acetate 2-fluoro-4-iodo-α-oxobenzene A mixture of 181.4 g (1324.3 mmol) of aluminum chloride and 1.1 L of dichloromethane was mixed with 168.6 g (1214.0 mmol) of ethyl chloroglyoxylate at room temperature while stirring. After stirring at room temperature for 1 hour, 250.0 g (1103.6 mmol) of 1-fluoro-3-iodobenzene was added and the mixture was stirred at room temperature for 1 day. After the reaction was complete, the reaction mixture was carefully poured onto ice and extracted with ethyl acetate. The organic layer was washed with saturated sodium thiosulfate aqueous solution and saline solution, dried over sodium sulfate, and the solvent was removed by vacuum distillation. The resulting pale yellowish-brown solid (298.9 g) was used in the next reaction without purification.

[0063] Preparation Example 1-2. Method for producing 2-fluoro-4-iodo-α-(hydroxyimino)benzene ethyl acetate. 298.9 g (927.9 mmol) of crude 2-fluoro-4-iodo-α-oxobenzene ethyl acetate obtained in Preparation Example 1-1 was dissolved in ethanol (900 mL) and stirred at room temperature. 78.2 g (1113.5 mmol) of hydroxylamine hydrochloride was added and refluxed for 6 hours. After the reaction was complete, the solvent was removed by vacuum distillation, and the mixture was diluted with ethyl acetate. The diluted solution was washed with water and saturated saline solution, dried over sodium sulfate, and the solvent was removed by vacuum distillation. The crude product obtained was purified by silica gel column chromatography (hexane / ethyl acetate = 4 / 1) to obtain the target product (191.9 g) as a white solid.

[0064] Preparation Example 1-3. Method for producing β-amino-2-fluoro-4-iodobenzeneethanol 191.9 g (569.4 mmol) of ethyl 2-fluoro-4-iodo-α-(hydroxyimino)benzene obtained in Preparation Example 1-2 was dissolved in tetrahydrofuran (600 mL) and stirred under ice cooling. 72.5 g (1822.1 mmol) of sodium borohydride was added, and then 233.3 g (911.0 mmol) of iodine dissolved in tetrahydrofuran (600 mL) was slowly added dropwise and refluxed for 5 hours. The reaction mixture was cooled on ice, water (300 mL) was carefully added dropwise, and then 88.2 g (2019.8 mmol) of sodium hydroxide and water (300 mL) were added and refluxed for a further 5 hours. After removing the solvent under reduced pressure, the sample was extracted with ethyl acetate and dried with sodium sulfate. The solvent was then removed under reduced pressure, and the resulting solid was washed with ethyl acetate to obtain the target product (54.7 g) as a pale yellowish-white solid.

[0065] Preparation Example 1-4. Method for producing N-{1-(2-fluoro-4-iodophenyl)-2-[(methylsulfonyl)oxy]ethyl}-2,6-difluorobenzamide. 73.0 g (259.8 mmol) of β-amino-2-fluoro-4-iodobenzeneethanol obtained in Preparation Example 1-3 was dissolved in tetrahydrofuran (520 mL), and 79.7 g (779.4 mmol) of triethylamine was added and the mixture was stirred under ice cooling. 46.4 g (259.8 mmol) of 2,6-difluorobenzoyl chloride dissolved in tetrahydrofuran (130 mL) was slowly added dropwise and the mixture was stirred at room temperature for 1 hour. After the amidation was complete, the reaction mixture was cooled on ice, and 35.9 g (311.8 mmol) of methanesulfonyl chloride dissolved in tetrahydrofuran (130 mL) was slowly added dropwise and the mixture was stirred at room temperature for 1 hour. After the reaction was complete, the precipitated solid was filtered off and washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure to obtain a yellow oil (129.8 g), which was used in the next reaction without further purification.

[0066] Preparation Example 1-5. Method for producing 2-(2,6-difluorophenyl)-4-(2-fluoro-4-iodophenyl)-4,5-dihydroxazole Crude N-{1-(2-fluoro-4-iodophenyl)-2-[(methylsulfonyl)oxy]ethyl}-2,6-difluorobenzamide obtained in Preparation Example 1-4 was dissolved in methanol (520 mL), and 28.0 g (649.5 mmol) of sodium hydroxide was added and the mixture was stirred at room temperature for 1 hour. After the reaction was complete, water was added to the reaction mixture, the solvent was removed by vacuum distillation, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over sodium sulfate. The solvent was then removed by vacuum distillation, and the crude product obtained was purified by silica gel column chromatography (hexane / ethyl acetate = 4 / 1) to obtain the target product (64.0 g) as a white solid.

[0067] Preparation Example 1-6. Method for preparing 2-(2,6-difluorophenyl)-4-[3-fluoro-4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-4,5-dihydroxazole (Compound 1) 20.2 g (50.0 mmol) of 2-(2,6-difluorophenyl)-4-(2-fluoro-4-iodophenyl)-4,5-dihydroxazole obtained in Preparation Example 1-5, 11.6 g (60.0 mmol) of 4-(trifluoromethyl)phenylboronic acid, 17.4 g (125.0 mmol) of potassium carbonate, and 0.2 g (1.0 mmol) of palladium acetate were dissolved in acetone / water = 1 / 1 mixed solvent (150 mL) and refluxed for 5 hours. After the reaction was complete, water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 3 / 1) to obtain the target product (15.0 g) as a white solid.

[0068] Preparation Example 2-1. Method for 3-chloro-4'-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-1,1'-biphenyl A mixture of 29.3 g (90.0 mmol) of 1-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzene, 18.9 g (117.0 mmol) of 3-chlorophenylboronic acid, 28.6 g (270.0 mmol) of sodium carbonate, and 300 mL of a 1,2-dimethoxyethane / water = 3 / 1 mixed solvent was degassed, and 5.3 g (4.5 mmol) of tetrakis(triphenylphosphine)palladium was added and the mixture was refluxed for 3 hours. After the reaction was complete, the organic layer was extracted with diisopropyl ether, washed with saturated brine, dried over sodium sulfate, and the solvent was removed by vacuum distillation. The crude product obtained was filtered through a glass filter and the solid was washed with hexane. The solvent was removed by vacuum distillation to obtain a colorless, transparent liquid. This liquid was purified by column chromatography (hexane) and subsequent vacuum distillation to obtain the target product (20.1 g) as a colorless, transparent oil.

[0069] Preparation Example 2-2. Method for producing N-[2-chloro-1-{3-chloro-4'-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl][1,1'-biphenyl]-4-yl}ethyl]-2,6-difluorobenzamide. 0.78 g (2.2 mmol) of 3-chloro-4'-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-1,1'-biphenyl obtained in Preparation Example 2-1 was mixed with 1.72 g (11.2 mmol) of trifluoromethanesulfonic acid and stirred under ice cooling. 0.50 g (2.0 mol) of N-(2-chloro-1-methoxyethyl)-2,6-difluorobenzamide was added and stirred for 30 minutes. After the reaction was complete, water was added and the mixture was extracted with diisopropyl ether. The organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine, then dried over sodium sulfate. The solvent was removed under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 3 / 1) to obtain the target product (0.59 g) as a white solid.

[0070] Preparation Example 2-3. Method for preparing 4-(3-chloro-4'-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl[1,1'-biphenyl]-4-yl)-2-(2,6-difluorophenyl)-4,5-dihydroxazole (Compound 57) 0.29 g (0.5 mmol) of N-[2-chloro-1-{3-chloro-4'-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl][1,1'-biphenyl]-4-yl}ethyl]-2,6-difluorobenzamide obtained in Preparation Example 2-2 and 1.6 mg (0.01 mmol) of tetrabutylammonium bromide were dissolved in dichloromethane (2 mL). Under ice-cold stirring, 66.0 mg (1.6 mmol) of sodium hydroxide dissolved in water (0.8 mL) was added, and the reaction mixture was heated to room temperature and stirred for 1 day. After the reaction was complete, the organic layer was extracted with dichloromethane, washed with saturated brine, and dried over sodium sulfate. The solvent was then removed under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 4 / 1) to obtain the target product (0.29 g) as a white solid.

[0071] Preparation Example 3-1. Method for preparing N-[1-(4-bromo-2-hydroxyphenyl)-2-chloroethyl]-2,6-difluorobenzamide 34.1 g (136.4 mmol) of N-(2-chloro-1-methoxyethyl)-2,6-difluorobenzamide and 26.5 g (150.0 mmol) of 3-bromophenol were dissolved in dichloromethane (200 mL) and stirred under ice cooling. 22.5 g (163.7 mmol) of aluminum chloride was added in small amounts, and after the addition was complete, the mixture was stirred at room temperature for 1 day. After the reaction was complete, the reaction mixture was carefully poured onto ice and extracted with dichloromethane. The organic layer was washed with water and saturated brine and dried over sodium sulfate. The solvent was then removed under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 1 / 1) to obtain the target product (12.2 g) as a white solid.

[0072] Preparation Example 3-2. Method for producing 5-bromo-2-[1-(2,6-difluorobenzoylamino)-2-chloroethyl]phenyl 1,1,1-trifluoromethanesulfonic acid. 6.0 g (15.4 mmol) of N-[1-(4-bromo-2-hydroxyphenyl)-2-chloroethyl]-2,6-difluorobenzamide obtained in Preparation Example 3-1 was dissolved in pyridine (30 mL) and stirred under ice cooling. 6.6 g (23.0 mmol) of trifluoromethanesulfonic anhydride was added in small increments, and after the addition was complete, the mixture was stirred at room temperature for 2 hours. After the reaction was complete, the pyridine was removed by vacuum distillation and the mixture was diluted with ethyl acetate. The diluted solution was washed with water and saturated saline solution, dried over sodium sulfate, and the solvent was removed by vacuum distillation to obtain an ochre solid (8.0 g). This ochre solid was used in the next reaction without purification.

[0073] Preparation Example 3-3. Method for producing 5-bromo-2-[2-(2,6-difluorophenyl)-4,5-dihydro-4-oxazolyl]phenyl 1,1,1-trifluoromethanesulfonic acid. 7.6 g (14.5 mmol) of crude 5-bromo-2-[1-(2,6-difluorobenzoylamino)-2-chloroethyl]phenyl 1,1,1-trifluoromethanesulfonic acid obtained in Preparation Example 3-2 and a catalytic amount of tetrabutylammonium bromide were dissolved in dichloromethane (20 mL) and stirred at room temperature. 1.3 g (29.0 mmol) of sodium hydroxide dissolved in water (5 mL) was added, and the mixture was stirred at room temperature for 1 day. After the reaction was complete, water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over sodium sulfate. The solvent was then removed under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 1 / 1) to obtain the target product (3.4 g) as a light brown solid.

[0074] Preparation Example 4-1. Method of 2-(4-bromo-2-chlorophenyl)oxirane Under stirring, 36.3 g (460.0 mmol) of dimethyl sulfoxide was heated to 100°C, and 44.4 g (345.0 mmol) of dimethyl sulfate was added and the mixture was stirred for 2 hours to generate trimethylsulfoxonium ions. This solution was dissolved in toluene (177 mL), and 1.5 g (4.6 mmol) of tetrabutylammonium bromide, 50.1 g (759 mmol) of potassium hydroxide, and 50.5 g (230.0 mmol) of 4-bromo-2-chlorobenzaldehyde were added and the mixture was stirred at room temperature. After the reaction was complete, the reaction mixture was washed with water and dried over sodium sulfate, and the solvent was removed by vacuum distillation. The crude product obtained was purified by silica gel column chromatography (hexane / ethyl acetate = 95 / 5) to obtain the target product (11.3 g) as a yellow oil.

[0075] Preparation Example 4-2. Method for producing β-azido-4-bromo-2-chlorobenzeneethanol. 11.2 g (48.0 mmol) of 2-(4-bromo-2-chlorophenyl)oxirane obtained in Preparation Example 4-1 was dissolved in water (96 mL), and 10.4 g (144.0 mmol) of sodium azide was added and the mixture was heated at 80°C. After the reaction was complete, the mixture was extracted with diisopropyl ether, the organic layer was washed with water and saturated saline solution, and dried with sodium sulfate. The solvent was then removed by vacuum distillation to obtain the target product (11.5 g) as a pale yellow solid.

[0076] Preparation Example 4-3. Method for producing β-amino-4-bromo-2-chlorobenzeneethanol 11.5 g (41.6 mmol) of β-azide-4-bromo-2-chlorobenzeneethanol obtained in Preparation Example 4-2 was dissolved in tetrahydrofuran (240 mL), and 19.9 g (72.0 mmol) of triphenylphosphine and 17.3 g (960 mmol) of water were added and the mixture was heated at 70°C. After the reaction was complete, the solvent was removed by distillation under reduced pressure, and methanol (173 mL) and 2 M hydrochloric acid (34.6 mL) were added and the mixture was stirred at room temperature for 2 hours. The aqueous layer was separated and organic impurities were removed by extraction with chloroform, and 9.6 g of sodium hydroxide was added to the aqueous layer and the mixture was stirred at room temperature for 30 minutes, followed by extraction with chloroform. The organic layer was dried over sodium sulfate, and the solvent was removed by distillation under reduced pressure to obtain the target product (9.5 g) as a pale yellow solid.

[0077] Preparation Example 5-1. Method for preparing methyl 4-bromo-2-chlorobenzeneacetate 100.4 g (394.3 mmol) of 4-bromo-2-chlorobenzeneacetic acid was dissolved in methanol (800 mL) and stirred at room temperature. 40.7 g (394.3 mmol) of concentrated sulfuric acid was added and refluxed for 7 hours. After the reaction was complete, the reaction mixture was cooled on ice, and 400 mL of saturated sodium bicarbonate aqueous solution was carefully added dropwise. The solvent was removed by vacuum distillation and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was then removed by vacuum distillation to obtain a pale yellowish-brown oil (99.7 g), which was used in the next reaction without purification.

[0078] Preparation Example 5-2. Method for producing 4-bromo-2-chloro-α-(hydroxyimino)benzenemethyl acetate. 89.2 g (338.4 mmol) of crude 4-bromo-2-chlorobenzenemethyl acetate obtained in Preparation Example 5-1 was dissolved in tetrahydrofuran (700 mL) and stirred at room temperature. 50.1 g (406.1 mmol) of isoamyl nitrite dissolved in tetrahydrofuran (300 mL) and sodium methoxide (5M methanol solution, 507.6 mmol) were added, and the mixture was stirred under a nitrogen atmosphere for 1 day. After the reaction was complete, the solvent was removed by vacuum distillation, and 10% hydrochloric acid was added dropwise until the precipitated solid was completely dissolved, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and then the solvent was removed by vacuum distillation to obtain the target product (97.1 g) as a yellow-orange oil.

[0079] Preparation Example 6-1. Method for preparing 4-bromo-1-iodo-2-(trifluoromethyl)benzene 49.5 g (206.2 mmol) of 4-bromo-2-(trifluoromethyl)aniline was dissolved in water (54 mL), and concentrated hydrochloric acid (54 mL) was added while vigorously stirring. The reaction mixture was heated to 60°C and stirred for 1 hour. The reaction mixture was cooled with ice, and while taking care to maintain the internal temperature at 0-5°C, 17.1 g (247.4 mmol) of sodium nitrite dissolved in water (28 mL) was added dropwise, followed by 37.7 g (226.8 mmol) of potassium iodide dissolved in water (28 mL). Once the generation of nitrogen gas had almost subsided, the reaction mixture was heated to 60°C and stirred for 2 hours, then allowed to cool to room temperature and diluted with hexane. The organic layer was washed with saturated sodium thiosulfate aqueous solution and saturated brine, then dried over sodium sulfate. The solvent was removed under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (hexane) to obtain the target product (62.0 g) as a yellow solid.

[0080] Preparation Example 6-2. Method for preparing 4-bromo-2-(trifluoromethyl)-α-oxobenzene ethyl acetate 16.0 g (45.5 mmol) of 4-bromo-1-iodo-2-(trifluoromethyl)benzene obtained in Preparation Example 6-1 and 1.3 g (9.1 mmol) of copper(I) bromide were dissolved in anhydrous tetrahydrofuran (90 mL) and cooled to -15°C to -12°C. 25 mL of isopropyl magnesium chloride (2 M tetrahydrofuran solution, 50.1 mmol) was added dropwise to the reaction mixture to maintain a temperature below -10°C. 6.8 g (50.1 mmol) of ethyl chloroglyoxylate was dissolved in anhydrous tetrahydrofuran (45 mL) and cooled to -15°C. This solution was added dropwise, ensuring the internal temperature did not exceed -10°C, and the mixture was vigorously stirred for 30 minutes. A 10% aqueous ammonium chloride solution was added. The reaction mixture was heated to 20°C to 25°C and stirred for 20 minutes. The aqueous layer was removed, and the solvent was removed by vacuum distillation. The crude product obtained was purified by silica gel column chromatography (hexane / ethyl acetate = 5 / 1) to obtain the target product (6.8 g) as a brown oil.

[0081] Preparation Example 7-1.4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzeneamine Method 50.3 g (540.0 mmol) of aniline, 141.0 g (648.0 mmol) of 85% sodium dithionite, 55.0 g (648.0 mmol) of sodium bicarbonate, and 18.7 g (54.0 mmol) of tetrabutylammonium bisulfate were added to a mixed solvent (1000 mL) of t-butyl methyl ether / water = 1 / 1 and stirred at room temperature. 201.9 g (648.0 mmol) of heptafluoroisopropyl iodide was added dropwise at room temperature and stirred for 1 day. After the reaction was complete, the solvent was removed by vacuum distillation, ethyl acetate was added to the reaction solution, washed with water and saturated brine, dried with sodium sulfate, and the solvent was removed by vacuum distillation. The crude product obtained was then distilled under reduced pressure to obtain the target product (122.9 g) as a pale yellow oil.

[0082] Preparation Example 7-2. Method for producing 4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]benzeneamine 13.1 g (50.0 mmol) of 4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzeneamine obtained in Preparation Example 7-1 was dissolved in methanol (50 mL) and stirred at room temperature, and sodium methoxide (5 M methanol solution, 200.0 mmol) was added. After refluxing the reaction mixture for 8 hours, it was cooled to room temperature, water was added, and it was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over sodium sulfate, and the solvent was removed by vacuum distillation. The resulting brown solid (11.7 g) was used in the next reaction without purification.

[0083] Preparation Example 7-3. Method for producing 1-iodo-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]benzene. 6.4 g (23.5 mmol) of crude 4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]benzeneamine obtained in Preparation Example 7-2 was dissolved in N,N-dimethylformamide (30 mL) and stirred under ice cooling. 11.8 mL (70.5 mmol) of 6 M hydrochloric acid and 20 mL (25.9 mmol) of aqueous sodium nitrite solution were added dropwise to the reaction mixture and stirred for 30 minutes. Then, 4.3 g (25.9 mmol) of potassium iodide was added, and the reaction mixture was heated to room temperature and stirred for 1 day. After the reaction was complete, the mixture was extracted with diisopropyl ether, and the organic layer was washed with saturated sodium thiosulfate aqueous solution, water, and saturated brine. After drying with sodium sulfate, the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane) to obtain the target product (5.6 g) as a yellow oil.

[0084] Preparation Example 7-4. Method for producing 2-{4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. 1.2 g (3.0 mmol) of 1-iodo-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]benzene obtained in Preparation Example 7-3, 0.9 g (3.6 mmol) of bis(pinacolato)diborone, 0.6 g (6.0 mmol) of potassium acetate, and 0.2 g (0.3 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (T) were dissolved in dimethyl sulfoxide (10 mL) and stirred at 100°C for 7 hours under a nitrogen atmosphere. After the reaction was complete, the reaction mixture was diluted with ethyl acetate and filtered by Celite. The resulting filtrate was washed with water and saturated brine, dried over sodium sulfate, and the solvent was removed by reduced pressure. The crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 3 / 1) to obtain the target product (1.0 g) as a white solid.

[0085] Preparation Example 8.2-{4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Preparation Example 7-1 129.1 g (494.5 mmol) of 4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzeneamine, 128.1 g (484.5 mmol) of bis(pinacolato)diborone, and 3.2 g (9.9 mmol) of benzoyl peroxide were dissolved in acetonitrile (700 mL) and stirred at room temperature. 85.0 g (741.7 mmol) of tert-butyl nitrite dissolved in acetonitrile (500 mL) was added and stirred for 1 day. After the reaction was complete, water was added to the reaction mixture to remove the solvent under reduced pressure and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane) to obtain the target product (73.8 g) as an orange solid.

[0086] Preparation Example 9. Method of preparing 4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]benzeneamine A reactor containing 0.5 g (10.0 mmol) of lithium aluminum hydride and tetrahydrofuran (5 mL) was purged with nitrogen and stirred under ice cooling. 1.3 g (5.0 mmol) of 4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzeneamine dissolved in tetrahydrofuran (5 mL) was added dropwise, and the reaction mixture was raised to room temperature and refluxed for 2 hours. After the reaction was complete, the reaction mixture was cooled with ice, and water (0.5 mL), 15% sodium hydroxide aqueous solution (0.5 mL), and water (1.5 mL) were carefully added dropwise. The reaction mixture was filtered through Celite, and the solvent was removed from the resulting filtrate under reduced pressure, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 3 / 1) to obtain the target product (0.5 g) as an orange oil.

[0087] Preparation Example 10.4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)benzeneamine Method 200.0 g (800.0 mmol) of copper sulfate pentahydrate was dissolved in warm water (700 mL) and the reaction mixture was allowed to cool to room temperature. Zinc powder was added until the color of the reaction mixture changed from blue transparent to colorless transparent. The supernatant was removed by decantation, the precipitated copper was washed with water, and 5% hydrochloric acid was added to remove excess zinc, and the mixture was stirred until no more hydrogen gas was generated. The activated copper was filtered, washed in water, ethanol, and diethyl ether in that order, and dried under vacuum to obtain activated copper. 6.7 g (30.0 mmol) of 4-iodoaniline, 12.7 g (36.0 mmol) of 1,1,2,2,3,3,4,4,4-nonafluorobutyliodide, 5.7 g (90.0 mmol) of activated copper, and 25 mL of dimethyl sulfoxide were added to a pressure-resistant tube. The tube was sealed with nitrogen gas and stirred at 100°C for 35 hours. After the reaction was complete, the solid in the reaction solution was filtered off and washed with dichloromethane. Water was added to the filtrate and extracted with dichloromethane. The organic layer was then washed with water and saturated brine and dried over sodium sulfate. The solvent was removed by reduced pressure, and the resulting crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 3 / 1) to obtain the target product (7.8 g) as a dark reddish-brown oil.

[0088] The example compounds listed in Table 1 below were prepared in the same manner as described above, or obtained in the same manner as described above.

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] <Examples of Formulations>

[0095] 1. A powder is obtained by mixing 10 parts by weight of the powder compound (1) with 90 parts by weight of talc and finely grinding it with a hammer mill.

[0096] 2. A wettable powder is obtained by mixing 10 parts by weight of the compound of wettable powder formula (1), 22.5 parts by weight of polyoxyethylene alkylaryl ether sulfate, and 67.5 parts by weight of clay, and then finely grinding this mixture with a hammer mill.

[0097] 3. Compound of flowable formulation (1) A flowable formulation is obtained by mixing 10 parts by weight of polyoxyethylene allylphenyl ether phosphate, 4 parts by weight of bentonite, 5 parts by weight of propylene glycol, 6 parts by weight of silicone-based defoaming agent, 0.5 parts by weight of 1,2-benzoisothiazolin-3-one, 0.2 parts by weight of water, and grinding the mixture using a wet grinder.

[0098] 4. An emulsion is obtained by mixing 10 parts by weight of the emulsion formula (1) compound, 15 parts by weight of polyoxyethylene tristilphenyl ether, and 75 parts by weight of xylene.

[0099] 5. Compound of granular formulation (1): Mix 5 parts by weight of calcium ligninsulfonate, 3 parts by weight of polycarboxylate, 3 parts by weight of calcium carbonate, and 89 parts by weight. Add water and knead, then extrude to granulate. After drying and sizing, granules are obtained. <Example of biological test>

[0100] Test Example 1-1 Existing Agent-Susceptible Diamondback Moth Control Test Leaf discs with a diameter of 5.0 cm were prepared from pot-grown radishes, and the active compound diluted to 1 ppm was sprayed on them (0.05% tween20 added). After air drying, first-instar larvae were released onto them. Then, they were left in a constant temperature room at 25°C (16 hours light period - 8 hours dark period). After 4 days of release, the viability of the insects was observed, and the mortality rate was calculated according to the following formula: Mortality rate (%) = {Number of dead insects / (Number of surviving insects + Number of dead insects)} × 100 The results are shown in Table 2. The compound of the present invention and comparative controls 1, 2, 3, 4, 5, and 6 showed high control performance. On the other hand, comparative control 7 had a mortality rate of 30% or less, indicating insufficient control performance. Control agent 1 (described in Japanese Patent Publication No. 3-232867) Control agent 2 (as described in Japanese Patent Publication No. 7-330518) Control agent 3 (described in Japanese Patent Publication No. 10-512859) Control agent 4 (described in Japanese Patent Publication No. 10-512859) Control agent 5 (described in Japanese Patent Publication No. 2001-521930) Control agent 6 (described in Japanese Patent Publication No. 2004-536828) Control agent 7 (described in Chinese patent CN102952056)

[0101] Test Example 1-2 Control Test for Existing Agent-Resistant Diamondback Moth Leaf discs with a diameter of 5.0 cm were prepared from pot-grown radishes, and an active compound diluted to 1 ppm was sprayed on them (with the addition of 0.05% tween20). After air drying, first-instar diamondback moth larvae resistant to diamide insecticides and IGR insecticides were released onto them. Subsequently, these were left in a constant temperature chamber at 25°C (16 hours light - 8 hours dark). After 4 days of release, the survival of the insects was observed, and the mortality rate was calculated according to the following formula: Mortality rate (%) = {Number of dead insects / (Number of surviving insects + Number of dead insects)} × 100 The results are shown in Table 2. The compound of the present invention showed high control performance. On the other hand, comparative controls 1, 2, 3, 4, 5, 6, and 7 had mortality rates of 30% or less, indicating insufficient control performance.

[0102]

[0103]

[0104] Test Example 1-3 Control Test for Citrus Thrips Susceptible to Existing Agents Circular leaf discs with a diameter of 3.0 cm were prepared from pot-grown green beans, and the active compound diluted to a predetermined concentration was sprayed onto them (0.05% tween20 added). After air drying, first-instar larvae were released onto them. Subsequently, these were left in a constant temperature room at 25°C (16 hours light period - 8 hours dark period). After 4 days of release, the viability of the insects was observed, and the mortality rate was calculated according to the following formula: Mortality rate (%) = {Number of dead insects / (Number of surviving insects + Number of dead insects)} × 100 The results are shown in Table 3. The compound of the present invention and comparative controls 1, 2, 3, 4, 5, and 6 showed high control performance. On the other hand, comparative control 7 had a mortality rate of less than 30% even at 100 ppm, indicating insufficient control performance.

[0105] Test Example 1-4 Control Test for Citrus Thrips Resistant to Existing Insecticides Circular leaf discs with a diameter of 3.0 cm were prepared from pot-grown green beans, and an active compound diluted to a predetermined concentration was sprayed onto them (0.05% tween20 added). After air drying, first-instar larvae of the citrus thrips, which are resistant to IGR insecticides, neonicotinoid insecticides, organophosphate insecticides, and synthetic pyrethroid insecticides, were released onto them. Subsequently, these were left in a constant temperature chamber at 25°C (16 hours light period - 8 hours dark period). After 4 days of release, the viability of the insects was observed, and the mortality rate was calculated according to the following formula: Mortality rate (%) = {Number of dead insects / (Number of surviving insects + Number of dead insects)} × 100 The results are shown in Table 3. The compound of the present invention showed high control performance. On the other hand, control groups 1, 2, 3, 4, 5, 6, and 7 had a mortality rate of less than 30% even at 100 ppm, indicating insufficient pest control performance.

[0106]

[0107] Test Example 1-5 Control Test for Existing Agent-Susceptible Spider Mites Leaf discs with a diameter of 3.0 cm were prepared from pot-grown green beans and inoculated with adult female mites. After 24 hours, the adult female mites were removed, the laid eggs were counted, and the active compound diluted to 100 ppm was sprayed on them (0.05% tween20 added). After air drying, the discs were left in a constant temperature room at 25°C (16 hours light - 8 hours dark). Seven days after release, the viability of the mites was observed, and the mortality rate was calculated according to the following formula: Mortality rate (%) = {(Number of unhatched eggs + Number of dead mites) / Number of laid eggs} × 100 The results are shown in Table 4.

[0108] Test Example 1-6 Control Test for Existing Agent-Resistant Spider Mites Leaf discs with a diameter of 3.0 cm were prepared from pot-grown green beans and inoculated with adult female spider mites resistant to IGR-type acaricides, mitochondrial electron transport chain complex I inhibitors, mitochondrial electron transport chain complex 3 inhibitors, organophosphate acaricides, and synthetic pyrethroid acaricides. After 24 hours, the adult females were removed, the laid eggs were counted, and the active compound diluted to 100 ppm was sprayed on them (with the addition of 0.05% tween20). After air drying, the discs were left in a constant temperature room at 25°C (16 hours light - 8 hours dark). After 7 days of release, the viability of the insects was observed, and the mortality rate was calculated according to the following formula: Mortality rate (%) = {(Number of unhatched eggs + Number of dead insects) / Number of laid eggs} × 100 The results are shown in Table 4. The compound of the present invention showed high control performance. On the other hand, control groups 1, 2, 3, 4, 5, 6, and 7 had mortality rates of 20% or less, indicating insufficient pest control performance.

[0109]

[0110]

[0111] Test Example 1-7 Control Test for Existing Agent-Resistant Rhinogobius rhizome Two leaf discs with a diameter of 3.0 cm were prepared from pot-grown radishes, and an active compound diluted to 1 ppm was sprayed on them (with the addition of 0.05% tween20). After air drying, third-instar larvae of Rhinogobius rhizome, which are resistant to diamide insecticides and IGRs, were released onto them. Subsequently, these were left in a constant temperature chamber at 25°C (16 hours light - 8 hours dark). Six days after release, the survival of the insects was observed, and the mortality rate was calculated according to the following formula: Mortality rate (%) = {Number of dead insects / (Number of surviving insects + Number of dead insects)} × 100 The results are shown in Table 5. The compound of the present invention showed high control performance. On the other hand, comparative controls 1-7 had mortality rates of 30% or less, indicating insufficient control performance.

[0112]

[0113] The compounds of the present invention have control efficacy against harmful organisms and are useful as active ingredients in pest control agents.

Claims

Equation (1): [In the formula, R １ This represents a C1-C6 perfluoroalkyl group in which one fluorine atom is substituted with a hydrogen atom or a C1-C6 alkoxy group, or is unsubstituted. R ２ represents a halogen atom, a C1-C6 alkoxy group, a trifluoromethyl group, or a trifluoromethanesulfonyloxy group. X represents a fluorine atom or a chlorine atom. A substituted biphenyloxazoline derivative compound represented by [the symbol shown]. The compound according to claim 1, wherein X is a fluorine atom. R ２ The compound according to claim 1, wherein is a halogen atom or a C1-C6 alkoxy group. R ２ The compound according to claim 1, wherein is a halogen atom or a C1-C4 alkoxy group. R ２ The compound according to claim 1, wherein is a fluorine atom, a chlorine atom, or a C1-C4 alkoxy group. R ２ The compound according to claim 1, wherein is a C1-C4 alkoxy group. R ２ The compound according to claim 1, wherein is a halogen atom. R ２ The compound according to claim 1, wherein is a fluorine atom or a chlorine atom. R １ The compound according to claim 1, wherein R is a C1-C6 perfluoroalkyl group. R １ The compound according to claim 1, wherein one fluorine atom is substituted with a hydrogen atom or a methoxy group, or is an unsubstituted C1-C4 perfluoroalkyl group. R １ The compound according to claim 9, wherein the compound is a C1-C4 perfluoroalkyl group. R １ The compound according to claim 10, wherein one fluorine atom is substituted with a hydrogen atom or a methoxy group, or is an unsubstituted C3-C4 perfluoroalkyl group. R １ The compound according to claim 11, wherein is a C3-C4 perfluoroalkyl group. 　 A pest control agent containing the compound and auxiliary agent described in any one of claims 1 to 13. 　 A method for controlling pests, comprising applying an effective amount of the compound described in any one of claims 1 to 13. 　 The method according to claim 15, comprising applying an effective amount of the compound described in any one of claims 1 to 13 to a harmful organism or a plant inhabited by a harmful organism or soil in which the plant is cultivated.

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