Method for controlling harmful arthropods or harmful nematodes using zoanthamines

Abstract

The present invention provides a method for controlling harmful arthropods or harmful nematodes. A compound represented by formula (I) [wherein: R1 represents a hydrogen atom or a methyl group; and R2 and R3 each represent a hydrogen atom or R2 and R3 together form an oxo group] or N-oxide thereof can be used for controlling harmful arthropods or harmful nematodes.

Description

[Technical Field]

[0001] This application claims priority to and the benefit of Japanese Patent Application No. 2021-031870, filed on March 1, 2021, the entire contents of which are incorporated herein by reference. The present invention relates to a method for controlling harmful arthropods or harmful nematodes using zoanthamines. [Background technology]

[0002] Various compounds have been investigated so far for the purpose of controlling harmful arthropods or harmful nematodes (see, for example, Non-Patent Document 1). On the other hand, Non-Patent Document 2 describes that norzoanthamine inhibits the growth of P388 murine leukemia cells. Non-Patent Document 3 describes that zoanthamines and their salts suppress IL-6 production by osteoblasts and also suppress the loss of bone mass and bone strength due to osteoporosis. [Prior art documents] [Non-patent literature]

[0003] [Non-Patent Document 1] The Pesticide Manual - 17th edition (BCPC) ISBN 978-1-901396-88-1 [Non-patent document 2] Heterocyclic Communications, 1995, 1(2-3), 207-214. [Non-patent document 3] Bulletin of the Chemical Society of Japan, 1998, 71, 771-779. Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present invention is to provide a method for controlling harmful arthropods or harmful nematodes. [Means for solving the problem]

[0005] The present invention is as follows. [1] Formula (I) [ka] [During the ceremony, R 1 represents a hydrogen atom or a methyl group, R 2 and R 3 each represents a hydrogen atom, or R 2 and R 3 together represent an oxo group. A method for controlling harmful arthropods or harmful nematodes, which comprises applying an effective amount of a compound represented by formula (I), or an N-oxide or a salt thereof (hereinafter, the compound represented by formula (I), or the N-oxide or the salt thereof will be referred to as the present compound) to harmful arthropods or harmful nematodes, or to a habitat of the harmful arthropods or harmful nematodes. [2] In formula (I), R 2 and R 3 The method according to [1], wherein each of [3] Formula (I) [ka] [During the ceremony, R 1 represents a hydrogen atom or a methyl group, R 2 and R 3 each represents a hydrogen atom, or R 2 and R 3 together represent an oxo group. A composition for controlling harmful arthropods or harmful nematodes, comprising a compound represented by the following formula: [4] The composition according to [3], further comprising one or more components selected from the group consisting of group (a), group (b), group (c), group (d), and group (e): Group (a): A group consisting of insecticidal active ingredients, acaricidal active ingredients and nematocidal active ingredients; Group (b): Fungicidally active ingredients; Group (c): Plant growth regulating components; Group (d): repellent components; Group (e): Biological control materials. [5] A method for controlling harmful arthropods or harmful nematodes, which comprises applying an effective amount of the composition according to [4] to harmful arthropods or harmful nematodes or to habitats of harmful arthropods or harmful nematodes. [6] Formula (I) [ka] [During the ceremony, R 1 represents a hydrogen atom or a methyl group, R 2 and R 3 each represents a hydrogen atom, or R 2 and R 3 together represent an oxo group. A seed or vegetative reproductive organ carrying an effective amount of a compound represented by the formula (I), or an N-oxide or a salt thereof, or an effective amount of the composition according to [4]. [7] Formula (I) [ka] [During the ceremony, R 1 represents a hydrogen atom or a methyl group, R 2 and R 3 each represents a hydrogen atom, or R 2 and R 3 together represent an oxo group. A composition for controlling harmful arthropods or harmful nematodes, comprising a compound represented by the following formula (I): or an N-oxide or a salt thereof, and an inert carrier. [Effects of the Invention]

[0006] According to the present invention, harmful arthropods or harmful nematodes can be controlled. DETAILED DESCRIPTION OF THE INVENTION

[0007] In this specification, Me represents a methyl group.

[0008] The present compound has stereoisomers, and includes each stereoisomer and a mixture of stereoisomers in any ratio.

[0009] The salt of the compound represented by formula (I) means an acid addition salt. Examples of acids that form acid addition salts include inorganic acids such as hydrogen chloride, phosphoric acid, and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid. Examples of salts of the compound represented by formula (I) include compounds represented by the following formula: [ka] [where, X - represents an anion formed by the loss of a proton from an acid, and the other symbols have the same meanings as above.

[0010] The following compounds are examples of the present compound.

[0011] [Embodiment 1] A compound represented by formula (I) or a salt thereof. [Aspect 2] In the present compound, R 2 and R 3 A compound in which each is a hydrogen atom. [Aspect 3] In the compound represented by formula (I), R 2 and R 3 and each represent a hydrogen atom, or a salt thereof. [Embodiment 4] Formula (II) [ka] [wherein the symbols have the same meanings as defined above], or an N-oxide or a salt thereof. [Aspect 5] A compound represented by formula (II) or a salt thereof. [Aspect 6] In aspect 4, R 2 and R 3 A compound in which each is a hydrogen atom. [Aspect 7] In the compound represented by formula (II), R 2 and R 3 and each represent a hydrogen atom, or a salt thereof.

[0012] Examples of the present compound include the following compounds: In the compound represented by formula (II), R 1 , R 2 and R 3 and each represent a hydrogen atom (hereinafter referred to as Compound 1 or norzoanthamine). In the compound represented by formula (II), R 1 is a methyl group, and R 2 and R 3 are each a hydrogen atom (hereinafter referred to as Compound 2 or zoanthamin). In the compound represented by formula (II), R 1 is a hydrogen atom, and R 2 and R 3 A compound in which these taken together form an oxo group (hereinafter referred to as compound 3 or norzoantaminone). In the compound represented by formula (II), R 1 is a methyl group, and R 2 and R 3 A compound in which these together form an oxo group (hereinafter referred to as compound 4 or zoantaminon). The hydrochloride salt of Compound 1 (hereinafter referred to as Compound 5). The hydrochloride salt of Compound 2 (hereinafter referred to as Compound 6). The hydrochloride salt of Compound 3 (hereinafter referred to as Compound 7). The hydrochloride salt of Compound 4 (hereinafter referred to as Compound 8). Acetate salt of Compound 1 (hereinafter referred to as Compound 9). Acetate salt of Compound 2 (hereinafter referred to as Compound 10). Acetate salt of Compound 3 (hereinafter referred to as Compound 11). Acetate salt of Compound 4 (hereinafter referred to as Compound 12). Sulfate of Compound 1 (hereinafter referred to as Compound 13). Sulfate of Compound 2 (hereinafter referred to as Compound 14). Sulfate of Compound 3 (hereinafter referred to as Compound 15). Sulfate of Compound 4 (hereinafter referred to as Compound 16). N-oxide of Compound 1 (hereinafter referred to as Compound 17). N-oxide of Compound 2 (hereinafter referred to as Compound 18). N-oxide of Compound 3 (hereinafter referred to as Compound 19). N-oxide of the present compound 4 (hereinafter referred to as the present compound 20).

[0013] In the compound of formula (I), R 1 , R 2 and R 3 are each a hydrogen atom (hereinafter referred to as compound 21). In the compound of formula (I), R 1 is a methyl group, and R 2 and R 3 are each a hydrogen atom (hereinafter referred to as compound 22). In the compound of formula (I), R 1 is a hydrogen atom, and R 2 and R 3 A compound in which these together represent an oxo group (hereinafter referred to as compound 23). In the compound of formula (I), R 1 is a methyl group, and R 2 and R 3 A compound in which these together form an oxo group (hereinafter referred to as compound 24). The hydrochloride salt of Compound 21 (hereinafter referred to as Compound 25). The hydrochloride salt of Compound 22 (hereinafter referred to as Compound 26). The hydrochloride salt of Compound 23 (hereinafter referred to as Compound 27). The hydrochloride salt of Compound 24 (hereinafter referred to as Compound 28). Acetate salt of Compound 21 (hereinafter referred to as Compound 29). Acetate salt of Compound 22 (hereinafter referred to as Compound 30). Acetate salt of Compound 23 (hereinafter referred to as Compound 31). Acetate salt of Compound 24 (hereinafter referred to as Compound 32). Sulfate of Compound 21 (hereinafter referred to as Compound 33). Sulfate of Compound 22 (hereinafter referred to as Compound 34). Sulfate of Compound 23 (hereinafter referred to as Compound 35). Sulfate of Compound 24 (hereinafter referred to as Compound 36). N-oxide of the present compound 21 (hereinafter referred to as the present compound 37). N-oxide of the present compound 22 (hereinafter referred to as the present compound 38). N-oxide of Compound 23 (hereinafter referred to as Compound 39). N-oxide of compound 24 (hereinafter referred to as compound 40).

[0014] Next, the method for producing the present compound will be explained.

[0015] Manufacturing method 1 The compound represented by formula (IV) (hereinafter referred to as compound (IV)) can be produced by reacting a compound represented by formula (III) (hereinafter referred to as compound (III)) with an oxidizing agent. [ka] [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent, such as halogenated hydrocarbons such as dichloromethane and chloroform, nitriles such as acetonitrile, alcohols such as methanol and ethanol, acetic acid, water, or a mixture of two or more of these. The oxidizing agent may, for example, be m-chloroperbenzoic acid. In the reaction, the oxidizing agent is usually used in a ratio of 1 to 3 moles per mole of compound (III). The reaction temperature is usually in the range of −10 to 50° C. The reaction time is usually in the range of 0.1 to 12 hours. After the reaction is complete, water is added to the reaction mixture, which is then extracted with an organic solvent. The organic layer is washed with an aqueous solution of a reducing agent (e.g., sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (e.g., sodium bicarbonate) as needed. The organic layer is dried and concentrated to obtain compound (IV). Compound (III) can be produced, for example, according to the methods described in JP-A-10-53589 and Pure and Applied Chemistry, 2007, 79, 651-665. Norzoanthamin, zoanthamin, norzoantaminon, and zoantaminon can also be produced, for example, according to the methods described in JP-A-10-53589 and Heterocyclic Communications, 1995, 1(2-3), 207-214.

[0016] Manufacturing method 2 Salts of the present compound can be produced, for example, according to the methods described in JP-A-10-53589, Bulletin of the Chemical Society of Japan, 1998, 71, 771, Chemistry - An Asian Journal, 2011, 6, 922-931, and Pure and Applied Chemistry, 2007, 79, 651-665.

[0017] This compound can be mixed or used in combination with one or more components (hereinafter referred to as this component) selected from the group consisting of the following groups (a), (b), (c), (d), and (e): The term "mixed or combined use" means that the present compound and the present ingredient are used simultaneously, separately or with an interval of time. When the present compound and the present ingredient are used simultaneously, the present compound and the present ingredient may be contained in separate preparations or may be contained in a single preparation. One aspect of the present invention is a composition (hereinafter referred to as Composition A) containing one or more components selected from the group consisting of Group (a), Group (b), Group (c), Group (d), and Group (e), and the present compound.

[0018] Group (a) consists of acetylcholinesterase inhibitors (e.g., carbamate pesticides, organophosphorus pesticides), GABA-gated chloride ion channel blockers (e.g., phenylpyrazole pesticides), sodium channel modulators (e.g., pyrethroid pesticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid pesticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride ion channel allosteric modulators (e.g., macrolide pesticides), juvenile hormone mimics, multi-site inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial insect midgut intima disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin pesticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport system complexes I, II, III, and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide pesticides), chordotonal organ modulators, and other insecticidal active ingredients, acaricidal active ingredients, and nematicidal active ingredients. These are described in the classification based on the mode of action of IRAC.

[0019] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acylamino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiration inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact active fungicides, and other fungicidal active ingredients. These are described in the classification based on the mode of action of FRAC.

[0020] Group (c) is a group of plant growth regulating components.

[0021] Group (d) is a group of repellent components.

[0022] Group (e) is a group of biocontrol materials consisting of bacteria, fungi, yeasts, protists, viruses, products produced by organisms, plants, and plant extracts.

[0023] Examples of combinations of the present component and the present compound are described below. For example, alanycarb + SX means a combination of alanycarb and SX. The abbreviation SX means any one of the present compounds selected from the present compounds 1 to 40. Further, all of the present components described below are known components and can be obtained from commercially available preparations or produced by known methods. When the present component is a microorganism, it can also be obtained from a microorganism depository institution. The numbers in parentheses represent CAS RN (registered trademark).

[0024] Combinations of the present component and the present compound of the above group (a): Abamectin + SX, Acephate + SX, Acequinocyl + SX, Acetamiprid + SX, Acetoprole + SX, Acrinathrin + SX, Acynonapyr + SX, Afidopyropen + SX, Afoxolaner + SX, Alanycarb + SX, Aldicarb + SX, Allethrin + SX, Alpha-cypermethrin + SX, Alpha-endosulfan + SX, Aluminium phosphide + SX, Amitraz + SX, Azadirachtin + SX, Azamethiphos + SX, Azinphos-ethyl + SX, Azinphos-methyl + SX, Azocyclotin + SX, Bendiocarb + SX, Benfluthrin + SX, Benfuracarb + SX, Bensultap + SX, Benzoximate + SX, Benzpyrimoxan + SX, Beta-cyfluthrin + SX, Beta-cypermethrin + SX, Bifenazate + SX, Bifenthrin + SX, Bioallethrin + SX, Bioresmethrin + SX, Bistrifluron + SX, Borax + SX, Boric acid + SX,Broflanilide + SX, Bromopropylate + SX, Buprofezin + SX, Butocarboxim + SX, Butoxycarboxim + SX, Cadusafos + SX, Calcium phosphide + SX, Carbaryl + SX, Carbofuran + SX, Carbosulfan + SX, Cartap hydrochloride + SX, Cartap + SX, Chinomethionat + SX, Chlorantraniliprole + SX, Chlordane + SX, Chlorethoxyfos + SX, Chlorfenapyr + SX, Chlorfenvinphos + SX, Chlorfluazuron + SX, Chlormephos + SX, Chloropicrin + SX, Chlorpyrifos + SX, Chlorpyrifos-methyl + SX, Chromafenozide + SX, Clofentezine + SX, Clothianidin + SX, Coumaphos + SX, Cryolite + SX, Cyanophos + SX, Cyantraniliprole + SX, Cyclaniliprole + SX, Cyclobutrifluram + SX, Cycloprothrin + SX, Cycloxaprid + SX,Cyenopyrafen + SX, cyetpyrafen + SX, Cyflumetofen + SX, Cyfluthrin + SX, Cyhalodiamide + SX, Cyhalothrin + SX, Cyhexatin + SX, Cypermethrin + SX, Cyphenothrin + SX, Cyproflanilide + SX, Cyromazine + SX, Dazomet + SX, Deltamethrin + SX, Demeton-S-methyl + SX, Diafenthiuron + SX, Diazinon + SX, Dichlorvos + SX, Dicloromezotiaz + SX, Dicofol + SX, Dicrotophos + SX, Diflovidazin + SX, Diflubenzuron + SX, Dimefluthrin + SX, Dimethoate + SX, Dimethylvinphos + SX, Dimpropyridaz + SX, Dinotefuran + SX, Disodium octaborate + SX, Disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, Doramectin + SX, Emamectin-benzoate + SX, Empenthrin + SX, Endosulfan + SX,EPN (O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, epsilon-metofluthrin + SX, epsilon-momfluorothrin + SX, esfenvalerate + SX, ethifencarb + SX, ethion + SX, ethiprole + SX, ethoprophos + SX, etofenprox + SX, etoxazole + SX, famphur + SX, fenamiphos + SX, fenazaquin + SX, fenbutatin oxide + SX, Fenitrothion + SX, fenmezoditiaz + SX, fenobucarb + SX, fenoxycarb + SX, fenpropathrin + SX, fenpyroximate + SX, fenthion + SX, fenvalerate + SX, fipronil + SX, flometoquin + SX, flonicamid + SX, fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, flubendiamide + SX, Fluchlordiniliprole + SX, flucycloxuron + SX, flucythrinate + SX, fluensulfone + SX,Flufenprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX, formetanate + SX, fosthiazate + SX, furamethrin + SX, furathiocarb + SX, gamma-cyhalothrin + SX GS-omega / kappa HXTX-Hv1a peptide + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, potassium salt of hop beta acid + SX, hydramethylnon + SX, hydroprene + SX, imicyafos + SX, imidacloprid + SX, imidaclothiz + SX, Imiprothrin + SX, indazapyroxamet + SX, indoxacarb + SX, isocycloseram + SX, isofenphos + SX,Isoprocarb + SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappa-tefluthrin + SX, kappa-bifenthrin + SX, kinoprene + SX, lambda-cyhalothrin + SX, lenoremycin + SX, lepimectin + SX, lime sulfur + SX, lotilaner + SX, lufenuron + SX SX, machine oil + SX, malathion + SX, mecarbam + SX, meperfluthrin + SX, metaflumizone + SX, metam + SX, methamidophos + SX, methidathion + SX, methiocarb + SX, methomyl + SX, methoprene + SX, methoxychlor + SX, methoxyfenozide + SX, methyl bromide + SX, metofluthrin + SX, metolcarb + SX Methoxadiazone + SX, mevinphos + SX, milbemectin + SX, milbemycin oxime + SX,Momfluorothrin + SX, monocrotophos + SX, moxidectin + SX, naled + SX, nicofluprole + SX, nicotine + SX, nicotine sulfate + SX, nitenpyram + SX, novaluron + SX, noviflumuron + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX Permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX, phosalone + SX, phosmet + SX, phosphamidon + SX, phosphine + SX, phoxim + SX, pirimicarb + SX, pirimiphos-methyl + SX, prallethrin + SX, profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX, Propylene glycol alginate + SX, prothiofos + SX, pyflubumide + SX, pymetrozine + SX,Pyraclofos + SX, pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyriminostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX SX, silafluofen + SX, sodium borate + SX, sodium metaborate + SX, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirodiclofen + SX, spiromesifen + SX, spiropidione + SX, spirotetramat + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride + SX Tartar emetic + SX, tau-fluvalinate + SX, tebufenozide + SX, tebufenpyrad + SX, tebupirimfos + SX,Teflubenzuron + SX, Tefluthrin + SX, Temephos + SX, Terbufos + SX, Tetrachlorantraniliprole + SX, Tetrachlorvinphos + SX, Tetradifon + SX, Tetramethrin + SX, Tetramethylfluthrin + SX, Tetraniliprole + SX, C, Theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap disodium + SX, thiosultap monosodium + SX, tioxazafen + SX, tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX, triazamate + SX, triazophos + SX, Trichlorfon + SX, trifluenfuronate + SX, triflumezopyrim + SX, triflumuron + SX, trimethacarb + SX, tyclopyrazoflor + SX, vamidothion + SX, 3,5-dimethylphenyl N-methylcarbamate (XMC) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (1445683-71-5) + SX, (2Z)-2-({2-fluoro-4-methyl-5-[(R)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (2377084-09-6) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX, 3-(4'-fluoro-2,4-dimethyl[1,1'-biphenyl]-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one (1031385-91-7) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, 1,4-dimethyl-2-[2-(3-pyridinyl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX。,

[0025] 上記群(b)の本成分と本化合物との組合せ: acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, benthiavalicarb-isopropyl + SX, benzovindiflupyr + SX, binapacryl + SX, biphenyl + SX, bitertanol + SX, bixafen + SX, blasticidin-S + SX, Bordeaux mixture + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionat + SX, chloroinconazide + SX, chloroneb + SX, chlorothalonil + SX,Chlozolinate + SX, Copper(II) acetate + SX, Copper(II) hydroxide + SX, Copper oxychloride + SX, Copper(II) sulfate + SX, Coumoxystrobin + SX, Cyazofamid + SX, Cyflufenamid + SX, Cymoxanil + SX, Cyproconazole + SX, Cyprodinil + SX, Dichlobentiazox + SX, Dichlofluanid + SX, Diclocymet + SX, Diclomezine + SX, Dicloran + SX, Diethofencarb + SX, Difenoconazole + SX, Diflumetorim + SX, Dimethachlone + SX, Dimethirimol + SX, Dimethomorph + SX, Dimoxystrobin + SX, Diniconazole + SX, Diniconazole-M + SX, Dinocap + SX, Dipotassium hydrogenphosphite + SX, Dipymetitrone + SX, Dithianon + SX, Dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt + SX, Dodemorph + SX,Dodine + SX, Edifenphos + SX, Enoxastrobin + SX, Epoxiconazole + SX, Etaconazole + SX, Ethaboxam + SX, Ethirimol + SX, Etridiazole + SX, Famoxadone + SX, Fenamidone + SX, Fenaminstrobin + SX, Fenarimol + SX, Fenbuconazole + SX, Fenfuram + SX, Fenhexamid + SX, Fenoxanil + SX, Fenpiclonil + SX, Fenpicoxamid + SX, Fenpropidin + SX, Fenpropimorph + SX, Fenpyrazamine + SX, Fentin acetate + SX, Fentin chloride + SX, Fentin hydroxide + SX, Ferbam + SX, Ferimzone + SX, Florylpicoxamid + SX, Fluazinam + SX, Flubeneteram + SX, Fludioxonil + SX, Flufenoxadiazam + SX, Flufenoxystrobin + SX, Fluindapyr + SX, Flumetylsulforim + SX, Flumorph + SX,Fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, folpet + SX, fosetyl + SX, fosetylaluminium + SX, fuberidazole + SX, furalaxyl + SX, furametpyr + SX, guazatine + SX, hexaconazole + SX, hymexazole + SX, imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX, ipfentrifluconazole + SX SX, ipflufenoquin + SX, iprobenfos + SX, iprodione + SX, iprovalicarb + SX,Isofetamid + SX, Isoflucypram + SX, Isoprothiolane + SX, Isopyrazam + SX, Isotianil + SX, Kasugamycin + SX, Kresoxim-methyl + SX, Laminarin + SX, Mancozeb + SX, Mandestrobin + SX, Mandipropamid + SX, Maneb + SX, Mefentrifluconazole + SX, Mepanipyrim + SX, Mepronil + SX, Meptyldinocap + SX, Metalaxyl + SX, Metalaxyl-M + SX, Metarylpicoxamid + SX, Metconazole + SX, Methasulfocarb + SX, Metiram + SX, Metominostrobin + SX, Metrafenone + SX, Methyltetraprole + SX, Myclobutanil + SX, Naftifine + SX, Nuarimol + SX, Octhilinone + SX, Ofurace + SX, Orysastrobin + SX, Oxadixyl + SX, Oxathiapiprolin + SX, oxine-copper + SX, Oxolinic acid + SX, Oxpoconazole + SX,Oxpoconazole fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, penthiopyrad + SX, phenamacril + SX, phosphorous acid + SX, phthalide + SX, picarbutrazox + SX, picoxystrobin + SX, piperalin + SX, polyoxins + SX, potassium hydrogencarbonate + SX, Potassium dihydrogenphosphite + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, pyraclostrobin + SX, pyrametostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX,Pyribencarb + SX, pyributicarb + SX, pyridaclomethyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriophenone + SX, pyrisoxazole + SX, pyroquilon + SX, quinconazole + SX, quinofumelin + SX, quinoxyfen + SX, quintozene + SX, quinoa saponins + SX, seboctylamine + SX, Sedaxane + SX, silthiofam + SX, simeconazole + SX, sodium hydrogencarbonate + SX, spiroxamine + SX, streptomycin + SX, sulfur + SX, tebuconazole + SX, tebufloquin + SX, teclofthalam + SX, tecnazene + SX, terbinafine + SX, tetraconazole + SX, thiabendazole + SX, thifluzamide + SX, thiophanate + SX, Thiophanate-methyl + SX, thiram + SX, thymol + SX, tiadinil + SX, tolclofos-methyl + SX,Tolfenpyrad + SX, Tolprocarb + SX, Tolylfluanid + SX, Triadimefon + SX, Triadimenol + SX, Triazoxide + SX, Triclopyricarb + SX, Tricyclazole + SX, Tridemorph + SX, Trifloxystrobin + SX, Triflumizole + SX, Triforine + SX, Triticonazole + SX, Validamycin + SX, Valifenalate + SX, Vinclozolin + SX, Zinc thiazole + SX, Zineb + SX, Ziram + SX, Zoxamide + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX,N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro- 6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX,methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX,3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX,1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole- It seems there is some repetition and an incomplete part in the original text. The translation remains as per the rules: 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX。,

[0026] Combination of this component of group (c) and this compound: 1-methylcyclopropene + SX, 1,3,5-triazinane-2,4,6-trithione + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat-chloride + SX, chlorpropham + SX, choline chloride + SX, cloprop + SX, cyanamide + SX, cyclanilide + SX,Daminozide + SX, decan-1-ol + SX, dichlorprop + SX, dikegulac + SX, dimethipin + SX, diquat + SX, ethephon + SX, ethychlozate + SX, flumetralin + SX, flurprimidol + SX, forchlorfenuron + SX, formononetin + SX, gibberellin A + SX, gibberellin A3 + SX, inabenfide + SX, Kinetin + SX, lipochitooligosaccharide SP104 + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexadione calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, pyroglutamic acid + SX, sintophen + SX, sodium 1-naphthaleneacetate + SX SX, sodium cyanate + SX, thidiazuron + SX, titanium apatite + SX, triapenthenol + SX,Tribufos + SX, trinexapac-ethyl + SX, uniconazole-P + SX, 2-(naphthalen-1-yl)acetamide + SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid + SX, methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol + SX.

[0027] Combination of the present component and the present compound in group (d) above: Anthraquinone + SX, deet + SX, icaridin + SX.

[0028] Combinations of the present component and the present compound in group (e) above: Abbreviata caucasica + SX, Acuaria spp. + SX, Agamermis decaudata + SX, Agrobacterium radiobacter strain K1026 + SX, Agrobacterium radiobacter strain K84 + SX, Agrobacterium vitis strain VAR03-1 + SX, Allantonema spp. + SX, Alternaria destruens strain 59 + SX, Alternaria destruens + SX, Ampelomyces quisqualis strain AQ10 + SX, Amphimermis spp. + SX, Arthrobotrys dactyloides + SX, Arthrobotrys superba + SX, Aschersonia aleyrodis + SX, Aspergillus flavus strain AF36 + SX, Aspergillus flavus strain NRRL21882 + SX, Aureobasidium pullulans strain DSM14940 + SX, Aureobasidium pullulans strain DSM14941 + SX, Azorhizobium caulinodans strain ZB-SK-5 + SX, Azotobacter chroococcum strain H23 + SX, Azotobacter chroocuccum + SX, Azotobacter vinelandii strain ATCC12837 + SX, Azotobacter + SX, Bacillus acidocaldarius + SX, Bacillus acidoterrestris + SX, Bacillus Albolactis + SX, Bacillus alcalophilus + SX, Bacillus alvei + SX, Bacillus aminoglucosidicus + SX, Bacillus aminovorans + SX,Bacillus amyloliquefaciens strain PTA-4838 (Aveo (trademark) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. Plantarum strain D747 +SX, Bacillus amylolyticus + SX, Bacillus aneurinolyticus + SX, Bacillus agri + SX, Bacillus atrophaeus + SX, Bacillus atrophaeus strain Abi05 + SX, Bacillus azotoformans + SX, Bacillus badius + SX, Bacillus cereus strain BP01 + SX,Bacillus cereus CNCM strain I-1562 + SX, Bacillus chitinosporus strain AQ746 + SX, Bacillus chitinosporus strain CM-1 + SX, Bacillus circulans + SX, Bacillus coagulans strain TQ33 + SX, Bacillus fastidiosus + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus lacticola + SX, Bacillus lactimorbus + SX, Bacillus lactis + SX, Bacillus lautus + SX, Bacillus Lentimorbus + SX, Bacillus lentus + SX, Bacillus licheniformis strain FMCH001 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus maroccanus + SX, Bacillus medusa + SX, Bacillus megaterium strain YFM3.25 + SX, Bacillus methylotrophicus strain BAC-9912 + SX, Bacillus metiens + SX, Bacillus mojavensis strain SR11 + SX, Bacillus mycoides strain AQ726 + SX, Bacillus mycoides isolate J + SX, Bacillus nematocida + SX, Bacillus nigrificans + SX, Bacillus nigrum + SX, Bacillus popilliae + SX,Bacillus psychrosaccharolyticus + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus siamensis + SX, Bacillus simplex strain CGF2856 + SX, Bacillus smithii + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus subtilis strain AFS032321 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain B246 + SX, Bacillus subtilis strain C-3102 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain DB102 + SX, Bacillus subtilis strain FMCH002 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX,Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Bacillus subtillis subsp. natto + SX, Bacillus subtilis strain RTI477 + SX, Bacillus subtilis strain N5 NRRL B-50391 + SX, Bacillus subtilis strain DSM17231 + SX, Bacillus tequilensis strain NII-0943 + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Bacillus thuringiensis strain EX297512 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX, Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai Serotype H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX,Bacillus thuringiensis subsp. Kurstaki strain CCT1306 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2371 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7673 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain M-200 + SX, Bacillus thuringiensis subsp. Kurstaki strain NCIM2514 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Kurstaki strain VBTS-2546 + SX, Bacillus thuringiensis subsp. Kurstaki strain Z-52, serotype H-3a,3b + SX, Bacillus thuringiensis subsp. morrisoni + SX,Bacillus thuringiensis subsp. Tenebriosis strain NB 176 + SX, Bacillus thuringiensis subsp. tenebriosis strain SA-10 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. var. colmeri + SX, Bacillus thuringiensis subsp. var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis subsp. var. dendrolimus + SX, Bacillus thuringiensis subsp. var. galleriae + SX, Bacillus thuringiensis subsp. israelensis strain BMP144 + SX, Bacillus thuringiensis subsp. israelensis strain AM65-52 + SX, Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 + SX, Bacillus thuringiensis subsp. israelensis strain EG2215 + SX, Bacillus thuringiensis subsp. israelensis strain SA3A + SX, Bacillus thuringiensis subsp. israelensis strain SUM-6218 + SX, Bacillus thuringiensis subsp. israelensis strain VCRC B17 serotype 11-14 + SX, Bacillus thuringiensis subsp. var. japonensis strain buibui + SX, Bacillus thuringiensis subsp. var. aegypti + SX,Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. Sandiego strain M-7 + SX, Bacillus thuringiensis var. T36 + SX, Bacillus velezensis + SX, Bacillus velezensis strain RTI301 + SX, Bacillus velezensis strain FZB42 + SX, bacteriophage of Clavibacter michiganesis + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX, Beauveria bassiana strain GHA + SX, Beauveria bassiana strain PPRI 5339 + SX, Beauveria bassiana strain IMI389521 + SX, Beauveria brongniartii + SX, Deladenus siridicola + SX, Bovienema spp. + SX, Brevibacillus brevis strain 2904 + SX, Brevibacillus brevis strain SS86-3 + SX, Brevibacillus brevis strain SS86-4 + SX, Brevibacillus brevis strain SS86-5 + SX, Brevibacillus laterosporus strain ATCC64 + SX, Brevibacillus laterosporus strain BPM3 + SX, Brevibacillus laterosporus strain G4 + SX, Brevibacillus laterosporus strain NCIMB 41419 + SX, Brevibacillus laterosporus strain NRS1111 + SX,Brevibacillus laterosporus strain NRS1645 + SX, Brevibacillus laterosporus strain NRS1647 + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Burkholderia cepacia type BA-7 + SX, Burkholderia rhinogensis strain A396 + SX, Cameronia spp. + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Candida spp. + SX, Chaetomium cupreum + SX, Chitwoodiella ovofilamenta + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Cladosporium cladosporioides strain H39 + SX, Conidiobolus obscurus + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-08 + SX, Contortylenchus spp. + SX, Cryptococcus albidus + SX, Culicimermis spp. + SX, Dactyllela ellipsospora + SX, Dactylaria thaumasia + SX, Delftia acidovorans strain RAY209 + SX, Dilophosphora alopecuri + SX, Diplotriaena spp. + SX, Empidomermis spp. + SX, Entomophthora virulenta + SX,Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Filipjevimermis leipsandra + SX, Fusarium oxysporum strain Fo47 + SX, Fusarium oxysporum strain RS-21 + SX, Fusarium oxysporum strain RS-25 + SX, Fusariumproliferatum + SX, Gastromermis spp. + SX, Gliocladium catenulatum strain J1446 + SX, gluconacetobacter diazotrophicus + SX, Gongylonema spp. + SX, Gynopoecilia pseudovipara + SX, Harpin protein + SX, Heterorhabditis bacteriophora + SX, Heterorhabditis baujardi + SX, Heterorhabditis heliothidis + SX, Heterorhabditis indica + SX, Heterorhabditis marelatus + SX, Heterorhabditis megidis + SX, Heterorhabditis zealandica + SX, Hexamermis spp. + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Hydromermis spp. + SX, Isaria fumosorosea + SX, Isomermis spp. + SX, Lactobacillus acidophilus + SX, Lactobacillus brevis + SX, Lactobacillus plantarum + SX, Lactobacillus spp. + SX, Lagenidium giganteum + SX, Lecanicillium lecanii KV01 + SX,Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX, Limnomermis spp. + SX, Lysobacter antibioticus strain 13-1 + SX, Lysobacter enzymogenes strain C3 + SX, Maupasina weissi + SX, Mermis nigrescens + SX, Mesomermis spp. + SX, Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52 + SX, Metarhizi, um flavoviride + SX, Metschnikowia fructicola strain NRRLY-30752 + SX, Microsphaeropsis ochracea + SX, Monacrosporium phymatopagum + SX, Mucor hiemalis + SX, Muscodor albus strain 620 + SX, Muscodor albus strain QST 20799 + SX, Muscodor albus strain SA13 + SX, Muscodor roseus strain A3-5 + SX, Myrothecium verrucaria strain AARC-0255 + SX, Neomesomermis spp. + SX, Neoparasitylenchus rugulosi + SX, Nomuraea rileyi strain CG128 + SX, Nomuraea rileyi strain GU87401 + SX, Nomuraea rileyi strain SA86101 + SX, Nomuraea rileyi strain SR86151 + SX, Nomuraea rileyi strain VA9101 + SX, Nosema locustae + SX, Octomyomermis spp. + SX, Ophiostoma piliferum strain D97 + SX, Isaria fumosorosea Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paecilomyces variotii strain Q-09 + SX, Paenibacillus alvei strain 2771 + SX, Paenibacillus alvei strain 46C3 + SX, Paenibacillus alvei strain III2E + SX, Paenibacillus alvei strain III3DT-1A + SX,Paenibacillus alvei strain T36 + SX, Paenibacillus macerans + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Paenibacillus popilliae + SX, Pandora delphacis + SX, Pantoea agglomerans strain E325 + SX, Pantoea vagans strain C9-1 + SX, Parasitaphelenchus spp. + SX, Parasitorhabditis spp. + SX, Parasitylenchus spp. + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria ramose + SX, Pasteuria usgae + SX, Pectobacterium carotovorum + SX, Penicillium bilaiae strain ATCC22348 + SX, Penicillium citrinum strain VFI-51 + SX, Penicillium vermiculatum + SX, Perutilimermis culicis + SX, Pasteuria thornei + SX, Phasmarhabditis hermaphrodita + SX, phlebiopsis gigantea strain VRA1992 + SX, Physaloptera spp. + SX, phytophthora palmivora + SX, Pichia anomala strain WRL-076 + SX, pichia guilliermondii strain Z1 + SX, pichia guilliermondii strain Z8 + SX, Pochonia chlamydosporia isolate strain PC10 + SX, Pochonia chlamydosporia + SX,Protrellatus spp. + SX, Pseudomonas aeruginosa strain PN1 + SX, Pseudomonas aeruginosa strain WS-1 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas cepacia type Wisconsin strain J82 + SX, Pseudomonas cepacia type Wisconsin strain M54 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SX, pseudomonas fluorescens strain 1629RS + SX, pseudomonas fluorescens strain A506 + SX, pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas fluorescens biover B strain XJ3 + SX, Pseudomonas fluorescens biover B strain XS18 + SX, Pseudomonas fluorescens biover A strain LRS12 + SX, Pseudomonas proradix + SX, Pseudomonas putida + SX, Pseudomonas reactans + SX, Pseudomonas resinovorans + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX,Pseudozyma flocculosa strain PF-A22UL + SX, Pterygodermatitis spp. + SX, Puccinia thlaspeos strain woad + SX, Purpureocillium lilacinum + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Rhodococcus globerulus strain AQ719 + SX, Romanomermis spp. + SX, Saccharomyces cerevisiae strain LAS02 + SX, Saccharomyces cerevisiae strain DDSF623 + SX, Sclerotinia minor strain IMI34414 + SX, Serratia entomophila + SX, Serratia marcescens strain 35 + SX, Serratia marcescens strain SRM + SX,100. Seuratum cadarachense + SX, Sphaerulariopsis spp. + SX, Spirura guianensis + SX, Sporothrix insectorum + SX, Steinernema bibionis + SX, Steinernema carpocapsae + SX, Steinernema feltiae + SX, Steinernema glaseri + SX, Steinernema krausei + SX, Steinernema riobrave + SX, Steinernema scapterisci + SX, Steinernema scarabaei + SX, Steinernema siamkayai + SX, Steinernema thai + SX, Steinernema spp. + SX, Strelkovimermis peterseni + SX, Streptomyces acidiscabies strain RL-110T + SX,Streptomyces candidus strain Y21007-2 + SX, Streptomyces colombiensis + SX, Streptomyces galbus strain QST6047 + SX, Streptomyces goshikiensis + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lavendulae + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Streptomyces microflavus strain AQ6121 + SX, Streptomyces prasinus + SX, Streptomyces rimosus + SX, Streptomyces saraceticus + SX, Streptomyces sp. strain NRRL No.B-30145 + SX, Streptomyces sp. strain WYE20 + SX, Streptomyces sp. strain WYE 324 + SX, Streptomyces venezuelae + SX, Subulura spp. + SX, Sulphuretylenchus elongatus + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Tetrameres spp. + SX, Thelohania solenopsis + SX, Thiobacillus spp. + SX, Trichoderma album + SX, Trichoderma asperelloides strain JM41R + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum T25 + SX, Trichoderma asperellum strain T34 + SX,Trichoderma asperellum strain SKT-1 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB 104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma harzianum rifai + SX,Trichoderma harzianum strain K2 + SX, Trichoderma harzianum strain F11Bab + SX, Trichoderma harzianum strain RR17Bc + SX, Trichoderma koningii + SX, Trichoderma lignorum + SX, Trichoderma polysporum strain IMI206039 + SX, Trichoderma spp. + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21, formaly Gliocladium virens GL-21 + SX, Trichoderma viride + SX, Trichoderma viride strain K5 + SX, Trichoderma viride strain NRRL B-S0S20 + SX, Tsukamurella paurometabola + SX, Typhula phacorrhiza strain 94671 + SX, Ulocladium oudemansii strain HRU3 + SX, Vairimorpha spp. strain Q-09 + SX, Variovorax paradoxus strain GF4526 + SX, Verticillium alboatrum strain WCS850 + SX, Verticillium chlamydosporium + SX, Verticillium dahliae + SX, Verticillium lecani strain NCIM1312 + SX, Virgibacillus pantothenticus strain ATCC14576 + SX, Virgibacillus pantothenticus strain DSM491 + SX, Wolbachia pipientis + SX, Xanthomonas campestris pv poae + SX,Xanthomonas campestris + SX, Xenorhabdus luminescens + SX, Xenorhabdus nematophila + SX, Zoophtora radicans + SX, Acaulospora spp. + SX, Ambispora spp. + SX, Archaeospora spp. + SX, Claroideoglomus spp. + SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Diversispora spp. + SX, Entrophospora spp. + SX, Funneliformis spp. + SX, Funneliformis mosseae + SX, Geosiphon spp. + SX, Gigaspora spp. + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus spp. + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Pacispora spp. + SX, Paraglomus spp. + SX, Paraglomus brasilianum + SX, Racocetra spp. + SX, Rhizophagus spp. + SX, Rhizophagus clarus + SX, Rhizophagus intraradices + SX, Rhizophagus irregularis + SX, Rhizophagus irregularis strain DAOM 197198 + SX, Scutellospora spp. + SX, Azorhizobium spp. + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense + SX, Azospirillum brasilense strain XOH + SX,Azospirillum brasilense strain Ab-V5 + SX, Azospirillum brazilense strain Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium spp. + SX, Bradyrhizobium elkanii + SX, Bradyrhizobium elkanii strain SEMIA 587 + SX, Bradyrhizobium elkanii strain SEMIA 5019 + SX, Bradyrhizobium japonicum + SX, Bradyrhizobium japonicum strain TA-11 + SX, Bradyrhizobium japonicum strain USDA 110 + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Bradyrhizobium spp. (Arachis) + SX, Bradyrhizobium spp. (Vigna) + SX, Delftia acidovorans + SX, Delftia acidovorans strain RAY209 + SX, Metylobacterium spp. + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Mesorhizobium loti + SX, Mesorhizobium spp. + SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. Viciae + SX,Rhizobium trifolii + SX, Rhizobium tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, Arkansas Fungus 18 + SX, Beauveria bassiana strain ATP02 + SX, Beauveria bassiana strain CG716 + SX, Candida oleophila isolate I-182 + SX, Colletotrichum gloeosporioides + SX, Cryptococcus flavescens + SX, Gliocladium roseum + SX, Glomus etunicatum + SX, Glomus iranicum + SX, Laccaria bicolor + SX, Laccaria laccata + SX, Lecanicillium muscarium strain 1 / 1 + SX, Metarhizium anisopliae var. acridum isolate IMI 330189 + SX, Isaria fumosorosea strain FE9901 + SX, Phlebiopsis + SX, Phoma macrostroma strain94-44B + SX, Acaulospora longula + SX, Ambispora leptoticha + SX, cell walls of Saccharomyces cerevisiae strain LAS117 + SX, Claroideoglomus claroideum + SX, Claroideoglomus luteum + SX, Pisolithus tinctorius + SX, Rhizopogon amylopogon + SX, Rhizopogon fulvigleba + SX, Rhizopogon luteolus + SX, Rhizopogon villosullus + SX, Scleroderma cepa + SX, Scleroderma citrinum + SX,Suillus granulatus + SX, Suillus punctatapies + SX, Trichoderma asperellum strain kd + SX, Trichoderma atroviride strain LU132 + SX, Trichoderma atroviride strain 77B + SX, Trichoderma atroviride strain K4 + SX, Trichoderma atroviride strain WW10TC4 + SX, Trichoderma harmatum strain TH382 + SX, Trichoderma lignorum strain TL-0601 + SX, Trichoderma saturnisporiu, m strain PBP-TH-001 + SX, Tsukamurella paurometabola strain C-924 + SX, Gluconactobacter diazotrophicus strain IMI504853 + SX, Clonostachys rosea strain IDAC 040913-01 + SX, Bacillus cereus Bromelia strain NRRL B-50766 + SX, Bacillus cereus Peumo strain NRRL B-50767 + SX, Bacillus thuringiensis Anemophyla strain NRRL B-50765 + SX, Trichoderma harzianuna strain Gomorteka NRRL 67322 + SX, Bacillus licheniformis strain DSM17236 + SX, Bacillus licheniformis strain copihue NRRL B-67023 + SX, Trichoderma reesei + SX, Corynebacterium flavescens strain B2575 + SX, Chlorella + SX, Methylobacterium isolate ISO01 + SX, Methylobacterium isolate ISO02 (NRRL B-50930) + SX, Methylobacterium isolate ISO03 (NRRL B-50931) + SX, Methylobacterium isolate ISO04 (NRRL B-50932) + SX, Methylobacterium isolate ISO07 + SX, Methylobacterium isolate ISO09 (NRRL B-50937) + SX, Methylobacterium isolate ISO10 (NRRL B-50938) + SX, Methylobacterium isolate ISO11 (NRRL B- 50939) + SX, Klebsiella variicola 137 + SX,Adoxophyes orana granulosis virus strain BV-0001 + SX, Anticarsia gemmatalis mNPV + SX, Autographa californica mNPV + SX, Cydia pomonella GV strain V15 + SX, Cydia pomonella GV strain V22 + SX, Cryptophlebia leucotreta GV + SX, Cydia pomonella GV strain CP4 + SX, Cydia pomonella GV strain R5 + SX, Dendrolimus punctatus cypovirus + SX, Helicoverpa armigera NPV strain BV-0003 + SX, Helicoverpa zea NPV + SX, Lymantria dispar NPV + SX, Mamestra brassicae NPV + SX, Mamestra configurata NPV + SX, Neodiprion abietis NPV + SX, Neodiprion lecontei NPV + SX, Neodiprion sertifer NPV + SX,Nosema locustae + SX, Orgyia pseudotsugata NPV + SX, Pieris rapae GV + SX, Plodia interpunctella GV + SX, Spodoptera exigua mNPV + SX, Spodoptera littoralis mNPV + SX, Spodoptera litura NPV + SX, BT crop protein Cry1Ab + SX, BT crop protein Cry1Ac + SX SX, BT crop protein Cry1Fa (BT crop protein Cry1Fa) + SX, BT crop protein Cry1A.105 (BT crop protein Cry1A.105) + SX, BT crop protein Cry2Ab (BT crop protein Cry2Ab) + SX, BT crop protein Vip3A (BT crop protein Vip3A) + SX, BT crop protein mCry3A (BT crop protein mCry3A) + SX, BT crop protein Cry3Ab (BT crop protein Cry3Ab) + SX, BT crop protein Cry3Bb (BT crop protein Cry3Bb) + SX, BT crop protein Cry34Ab1 / Cry35Ab1 (BT crop protein Cry34Ab1 / Cry35Ab1) + SX, chitin + SX, colletochlorin B + SX, concanamycin A + SX, ryanodine + SX, cevadine + SX, veratridine + SX,Pyrethrin I + SX, pyrethrin II + SX, cinerin I + SX, cinerin II + SX, jasmolin I + SX, jasmolin II + SX, oak leaves and bark of Quercus + SX, dried leaves of Dryopteris filix-mas + SX, Artemisia absinthium extract + SX, Cassia nigricans extract + SX, Clitoria ternatea extract + SX, Symphytum officinale extract + SX, Chenopodium ambrosioides extract + SX, Tansy extract (Tanacetum vulgare extract) + SX, Stinging nettle extract (Urtica dioica extract) + SX, Mistletoe extract (Viscum album extract) + SX, Chenopodium anthelminticum seed oil (oil of the seeds of Chenopodium anthelminticum) + SX, Quassia amara wood extract + SX, Tea tree extract (Melaleuca alternifolia extract) + SX, Reynoutria sachalinensis extract + SX, Lupine seedling cotyledon extract (BLAD) + SX, Garlic extract (Allium sativum extract) + SXExtract of Equisetum arvense + SX, extract of Tropaeolum majus + SX, extract of Azadirachta indica + SX, Quillaja extract + SX, yellow mustard powder + SX, seed extract of Schoenocaulon spp. + SX, extract of Pyrethrum + SX, Gougerotin + SX, matrine + SX, ascaridole + SX, capsicin + SX, deguelin + SX, nootkatone + SX, pellitorine + SX, piperine + SX, extract from Swinglea glutinosa + SX, cytokinin + SX, N,N'-diformylurea + SX, salicylic acid + SX.,

[0029] The ratio of the present compound to the present component is not particularly limited, but examples of the weight ratio (present compound: present component) include 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc.

[0030] The present compound has efficacy against harmful arthropods such as harmful insects and harmful mites, and harmful nematodes. Examples of harmful arthropods and harmful nematodes include the following.

[0031] Hemiptera: Delphacidae such as Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodes orizicolus; Cicadellidae such as Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Empoasca onukii, Empoasca fabae, Dalbulus maidis, Cofana spectra, Amrasca biguttula biguttula; Aphrophoridae such as Philaenus spumarius; Cercopidae such as Mahanarva posticata, Mahanarva fimbriolata;Aphididae such as Aphis fabae, Aphis glycines, Aphis gossypii, Aphis pomi, Aphis spiraecola, Myzus persicae, Brachycaudus helichrysi, Brevicoryne brassicae, Dysaphis plantaginea (rosy apple aphid), Lipaphis erysimi, Macrosiphum euphorbiae, Aulacorthum solani, Nasonovia ribisnigri, Rhopalosiphum padi, Rhopalosiphum maidis, Toxoptera citricida, Hyalopterus pruni, Melanaphis sacchari, Tetraneura nigriabdominalis, Ceratovacuna lanigera, Eriosoma lanigerum, Sitobion avenae (English grain aphid), etc.; Phylloxeridae such as Daktulosphaira vitifoliae, Phylloxera devastatrix, Phylloxera notabilis, Phylloxera russelae, etc.Adelgidae such as Adelges tsugae, Adelges piceae, Aphrastasia pectinatae; Pentatomidae such as Scotinophara lurida, Scotinophara coarctata, Nezara antennata, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Eysarcoris annamita, Halyomorpha halys, Nezara viridula, Euschistus heros, Piezodorus guildinii, Oebalus pugnax, Dichelops melacanthus; Cydnidae such as Scaptocoris castanea; Alydidae such as Riptortus clavatus, Leptocorisa chinensis, Leptocorisa acuta; Coreidae such as Cletus punctiger, Leptoglossus australis; Lygaeidae such as Cavelerius saccharivorus, Togo hemipterus, Blissus leucopterus;Miridae such as Trigonotylus caelestialium, Stenotus rubrovittatus, Stenodema calcarata, and Lygus lineolaris; Aleyrodidae such as Trialeurodes vaporariorum, Bemisia tabaci, Dialeurodes citri, Aleurocanthus spiniferus, Aleurocanthus camelliae, and Pealius euryae; Diaspididae such as Abgrallaspis cyanophylli, Aonidiella aurantii, Diaspidiotus perniciosus, Pseudaulacaspis pentagona, Unaspis yanonensis, and Unaspis citri; Coccidae such as Ceroplastes rubens; Margarodidae such as Icerya purchasi and Icerya seychellarum;Pseudococcidae such as Phenacoccus solani, Phenacoccus solenopsis, Planococcus kraunhiae, Pseudococcus comstocki, Planococcus citri, Pseudococcus calceolariae, Pseudococcus longispinus, Brevennia rehi, etc.; Psyllidae such as Diaphorina citri, Trioza erytreae, Cacopsylla pyrisuga, Cacopsylla chinensis, Bactericera cockerelli, Cacopsylla pyricola, etc.; Tingidae such as Corythucha ciliata, Corythucha marmorata, Stephanitis nashi, Stephanitis pyrioides, etc.; Cimicidae such as Cimex lectularius, Cimex hemipterus, etc.; Cicadidae such as Quesada gigas, etc.; Reduviidae such as Triatoma infestans, Triatoma rubrofasciata, Triatoma dimidiata, Rhodonius prolixus, etc.

[0032] Lepidoptera: Chilo suppressalis, Dark-headed stem borer, Chilo polychrysus, White stem borer, Scirpophaga innotata, Scirpophaga incertulas, Rupela albina, Rice leaf borer, Cnaphalocrocis medinalis, Marasmia patnalis, Rice casino borer, Marasmia exigua, Cotton borer, Notarcha derogata, European corn borer, Ostrinia furnacalis, European corn borer, Hellula undalis, Black-spotted corn borer, Herpetogramma luctuosale, Rice stalk moth, Nymphula Crambidae, such as the Japanese corn moth (Elasmopalpus lignosellus), the Indian meal moth (Plodia interpunctella), the Japanese two-spotted moth (Euzophera batangensis), and the Japanese striped moth (Cadra cautella);Spodoptera litura, Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia, Naranga aenescens, Spodoptera frugiperda, Spodoptera exempta, Spodoptera cosmioides, Spodoptera eridania, Agrotis ipsilon, Autographa nigrisigna, Plusia festucae, Chrysodeixis includens, Trichoplusia spp., Heliothis spp. such as Heliothis virescens, Helicoverpa spp. such as Helicoverpa armigera and Helicoverpa zea, Anticarsia gemmatalis, Alabama argillacea, Noctuidae such as Hydraecia immanis; Pieridae such as Pieris rapae;Tortricidae such as Grapholita molesta, Grapholita dimorpha, Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, Cydia pomonella, Tetramoera schistaceana, Epinotia aporema, Citripestis sagittiferella, Lobesia botrana, etc.; Gracillariidae such as Caloptilia theivora, Phyllonorycter ringoniella, etc.; Carposinidae such as Carposina sasakii, etc.; Lyonetiidae such as Leucoptera coffeella, Lyonetia clerkella, Lyonetia prunifoliella, etc.; Lymantriidae such as Lymantria spp. including Lymantria dispar, Euproctis spp. including Euproctis pseudoconspersa, etc.; Plutellidae such as Plutella xylostella, etc.Gelechiidae (Gelechiidae) such as Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, and Tuta absoluta; Arctiidae (Arctiidae) such as Hyphantria cunea; Castniidae (Castniidae) such as Telchin licus; Cossidae (Cossus insularis); Geometridae (Geometridae) such as Ascotis selenaria; Limacodidae (Limaculidae) such as Parasa lepida; and Stathmopoda Stathmopodidae such as Acherontia masinissa; Sphingidae such as Acherontia lachesis; Sesiidae such as Nokona feralis, Synanthedon hector, and Synanthedon tenuis; Hesperiidae such as Parnara guttata; Tineidae such as Tinea translucens and Tineola bisselliella;

[0033] Order Thysanoptera: Thripidae such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, Echinothrips americanus, Scirtothrips perseae, etc.; Phlaeothripidae such as Haplothrips aculeatus, etc.

[0034] Diptera: Anthomyiidae such as Delia platura, Delia antiqua, Pegomya cunicularia, etc.; Ulidiidae such as Tetanops myopaeformis, etc.; Agromyzidae such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, Chromatomyia horticola, etc.; Chloropidae such as Chlorops oryzae, etc.; Tephritidae such as Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratitis capitata, Rhagoletis pomonella, Rhacochlaena japonica, etc.; Ephydridae such as Hydrellia griseola, Hydrellia philippina, Hydrellia sasakii, etc.; Drosophilidae such as Drosophila suzukii, Drosophila melanogaster, etc.; Phoridae such as Megaselia spiracularis, etc.; Psychodidae such as Clogmia albipunctata, etc.; Sciaridae such as Bradysia difformis, etc.;Cecidomyiidae such as Hessian fly (Mayetiola destructor) and rice gall midge (Orseolia oryzae); Diopsidae such as Diopsis macrophthalma; Glossinidae such as Glossina palpalis and Glossina morsitans; Simuliidae such as Simulium japonicum and Simulium damnosum; Phlebotominae; Tipulidae such as Tipula aino, common crane fly (Tipula oleracea), and European crane fly (Tipula paludosa); Culicidae such as Culex pipiens pallens, Culex tritaeniorhynchus, Culex pipiens f. molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, Aedes albopictus, Aedes aegypti, Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, and Anopheles minimus; Simuliidae such as Prosimulium yezoensis and Simulium ornatum; Tabanidae such as Tabanus trigonusMuscidae, such as the house fly (Musca domestica), the giant house fly (Muscina stabulans), the stable fly (Stomoxys calcitrans), and the horn fly (Haematobia irritans); Calliphoridae; Sarcophagidae; Chironomidae, such as the giant midge (Chironomus plumosus), the Japanese midge (Chironomus yoshimatsui), and the gray midge (Glyptotendipes tokunagai); Fannidae;

[0035] Coleoptera: Diabrotica spp. (e.g., Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded cucumber beetle (Diabrotica balteata), Cucumber beetle (Diabrotica speciosa), etc.), Bean leaf beetle (Cerotoma trifurcata), Cereal leaf beetle (Oulema melanopus), Striped flea beetle (Phyllotreta striolata), Crucifer flea beetle (Phyllotreta cruciferae), Western black flea beetle (Phyllotreta pusilla), Stem flea beetle (Psylliodes chrysocephala), Hop flea beetle (Psylliodes punctulata), Colorado potato beetle (Leptinotarsa decemlineata), Rice leaf beetle (Oulema oryzae), Grape colaspis (Colaspis brunnea), Corn flea beetle (Chaetocnema pulicaria), Sweet potato flea beetle (Chaetocnema confinis), Potato flea beetle (Epitrix cucumeris), Rice hispa (Dicladispa armigera), Southern corn leaf beetle (Myochrous denticollis), Four-spotted leaf beetle (Laccoptera quadrimaculata), Tobacco flea beetle (Epitrix hirtipennis), etc. of Chrysomelidae; Seed corn beetle (Stenolophus lecontei), Slender seed corn beetle (Clivina impressifrons), etc. of Carabidae;Scarabaeidae such as Anomala cuprea, Anomala rufocuprea, Anomala albopilosa, Popillia japonica, Heptophylla picea, Rhizotrogus majalis, Tomarus gibbosus, Holotrichia spp., Phyllophaga spp. such as Phyllophaga crinita, and Diloboderus spp. such as Diloboderus abderus; Anthriibidae such as Araecerus coffeae; Aponidae such as Cylas formicarius; Bruchidae such as Zabrotes subfasciatus; Scolytidae such as Tomicus piniperda and Hypothenemus hampei;Euscepes postfasciatus, Hypera postica, Sitophilus zeamais, Sitophilus oryzae, Sitophilus granarius, Echinocnemus squameus, Lissorhoptrus oryzophilus, Rhabdoscelus lineaticollis, Anthonomus grandis, Sphenophorus venatus, Sphenophorus callosus, Sternechus subsignatus, Sphenophorus levis, Scepticus griseus, Scepticus uniformis, Aracanthus spp. such as Aracanthus mourei, Curculionidae such as Eutinobothrus brasiliensis; Tenebrionidae such as Tribolium castaneum, Tribolium confusum, Alphitobius diaperinus; Coccinellidae such as Epilachna vigintioctopunctata; Bostrychidae such as Lyctus brunneus, Rhizopertha dominica; Ptinidae; Cerambycidae such as Anoplophora malasiaca, Migdolus fryanus, Aromia bungii;Click beetles (Elateridae) such as Melanotus okinawensis, Agriotes fuscicollis, Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., Aeolus spp., etc.; rove beetles (Staphylinidae) such as Paederus fuscipes, etc.; dermestid beetles (Dermestidae) such as Anthrenus verbasci, Dermestes maculates, Trogoderma granarium, etc.; anobiid beetles (Anobiidae) such as Lasioderma serricorne, Stegobium paniceum, etc.; flat bark beetles (Laemophloeidae) such as Cryptolestes ferrugineus, etc.; minute brown scavenger beetles (Silvanidae) such as Oryzaephilus surinamensis, etc., and sap beetles (Nitidulidae) such as Brassica gethes aeneus, etc.

[0036] Orthoptera: Acrididae such as Locusta migratoria, Dociostaurus maroccanus, Chortoicetes terminifera, Nomadacris septemfasciata, Locustana pardalina, Anacridium melanorhodon, Calliptamus italicus, Melanoplus differentialis, Melanoplus bivittatus, Melanoplus sanguinipes, Melanoplus femurrubrum, Camnula pellucida, Schistocerca gregaria, Gastrimargus musicus, Austracris guttulosa, Oxya yezoensis, Oxya japonica, Patanga succincta, etc.; Gryllotalpidae such as Gryllotalpa orientalis, etc.; Gryllidae such as Acheta domestica, Teleogryllus emma, etc.; Tettigoniidae such as Anabrus simplex, etc.

[0037] Hymenoptera: Tenthredinidae such as Athalia rosae and Athalia japonica; Solenopsis spp. such as Solenopsis invicta and Solenopsis geminata, Atta spp. such as Atta capiguara, Acromyrmex spp., Paraponera clavata, Ochetellus glaber, Monommorium pharaonis, Linepithema humile, Formica japonica, Pristomyrmex punctutus, Pheidole noda, Pheidole megacephala, Camponotus japonicus, Camponotus obscuripes, etc. of Camponotus spp., Pogonomyrmex spp. such as Pogonomyrmex occidentalis, Wasmania spp. such as Wasmania auropunctata, Formicidae such as Anoplolepis gracilipes; Vespidae such as Vespa mandarinia, Vespa simillima, Vespa analis, Vespa velutina, Polistes jokahamae, etc.; Siricidae such as Urocerus gigas; Bethylidae.

[0038] Order Blattodea: Family Ectobiidae such as Blattella germanica; Family Blattidae such as Periplaneta fuliginosa, Periplaneta americana, Periplaneta australasiae, Periplaneta brunnea, Blatta orientalis; Family Termitidae such as Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus, Reticulitermes miyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, Cornitermes cumulans.

[0039] Order Siphonaptera: Pulicidae such as Pulex irritans, Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Echidnophaga gallinacea, etc.; Hectopsyllidae such as Tunga penetrans, etc.; Ceratophyllidae such as Nosopsyllus fasciatus, etc.

[0040] Psocodea: Pediculidae such as Pediculus humanus capitis; Pthiridae such as Pthirus pubis; Haematopinidae such as Haematopinus eurysternus, Haematopinus suis; Linognathidae such as Linognathus vituli, Linognathus ovillus, Solenopotes capillatus; Bovicoliidae such as Bovicola bovis, Bovicola ovis, Bovicola breviceps, Damalinia forficula, Werneckiella spp.; Trichodectidae such as Trichodectes canis, Felicola subrostratus; Menoponidae such as Menopon gallinae, Menacanthus stramineus, Trinoton spp.; Trimenoponidae such as Cummingsia spp.; Trogiidae such as Trogium pulsatorium; Liposcelididae or Liposcelidae such as Liposcelis corrodens, Liposcelis bostrychophila, Liposcelis pearmani, Liposcelis entomophila.

[0041] Thysanura: Lepismatidae such as Ctenolepisma villosa and Lepisma saccharina.

[0042] Acari: Tetranychidae, such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, and Oligonychus spp.; Aculops pelekassi, Aculops citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, and Aculus spp. Eriophyidae, such as Aceria diospyri, Aceria tosichella, and Shevtchenkella sp.; Tarsonemidae, such as Polyphagotarsonemus latus; Tenuipalpidae, such as Brevipalpus phoenicis; Tuckerellidae;Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Dermacentor andersoni, Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Ixodes pacificus, Ixodes holocyclus, Ixodes ricinus, Amblyomma americanum, Amblyomma maculatum, Rhipicephalus microplus, Rhipicephalus annulatus, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus decoloratus, etc. of the family Ixodidae; Argas persicus, Ornithodoros hermsi, Ornithodoros turicata, etc. of the family Argasidae; Tyrophagus putrescentiae, Tyrophagus similis, etc. of the family Acaridae; Dermatophagoides farinae, Dermatophagoides pteronyssinus, etc. of the family Pyroglyphidae;Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Chelacaropsis moorei, Cheyletiella yasguri, etc.; Psoroptidae such as Psoroptes ovis, Psoroptes equi, Knemidocoptes mutans, Otodectes cynotis, Chorioptes spp., etc.; Sarcoptidae such as Notoedres cati, Notoedres muris, Sarcoptes scabiei, etc.; Listrophoridae such as Listrophorus gibbus, etc.; Dermanyssidae such as Dermanyssus gallinae, etc.; Macronyssidae such as Ornithonyssus sylviarum, Ornithonyssus bacoti, etc.; Varroidae such as Varroa jacobsoni, etc.; Demodicidae such as Demodex canis, Demodex cati, etc.; Trombiculidae such as Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium scutellare, etc.

[0043] Order Araneae: Eutichuridae such as Cheiracanthium japonicum, etc.; Theridiidae such as Latrodectus hasseltii, etc. Order Polydesmida: Family Paradoxosomatidae such as Oxidus gracilis and Nedyopus tambanus. Order Isopoda: Family Armadillidiidae such as Armadillidium vulgare. Class Chilopoda: Family Scutigeridae such as Thereuonema hilgendorfi; Family Scolopendridae such as Scolopendra subspinipes; Family Ethopolyidae such as Bothropolys rugosus.

[0044] Nematoda: Aphelenchoididae such as Aphelenchoides besseyi; Pratylenchidae such as Pratylenchus coffeae, Pratylenchus brachyurus, Pratylenchus neglectus, Radopholus similis; Heteroderidae such as Meloidogyne javanica, Meloidogyne incognita, guava root - knot nematodes (Meloidogyne enterolobii), Meloidogyne hapla, Heterodera glycines, Globodera rostochiensis, Globodera pallida; Hoplolaimidae such as Rotylenchulus reniformis; Anguinidae such as Nothotylenchus acris, Ditylenchus dipsaci; Tylenchulidae such as Tylenchulus semipenetrans; Longidoridae such as Xiphinema index; Trichodoridae; Parasitaphelenchidae such as Bursaphelenchus xylophilus; Trichuridae such as Trichuris suis, Trichuris ovis, Trichuris discolorCapillariidae such as Capillaria suis, Calodium hepaticum, Paracapillaria philippinensis, Pearsonema plica, Pearsibena spp.; Trichinellidae such as Trichinella spiralis, Trichinella britovi; Strongyloididae such as Strongyloides papillosus, Strongyloides planiceps, Strongyloides ransomi, Strongyloides stercoralis; Strongylidae such as Strongylus edentatus, Strongylus vulgaris, Triodontophorus spp., Oesophagodontus spp., Cylicostephanus spp.; Chabertiidae such as Oesophagostomum dentatum, Oesophagostomum radiatum, Chabertia ovina; Stephanuridae such as Stephanurus dentatus; Dioctophymatidae such as Dioctophyme renale; Ancylostomatidae such as Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma duodenale, Uncinaria stenocephala, Bunostomum phlebotomum, Bunostomum trigonocephalum, Globocephalus spp.; Syngamidae such as Syngamus skrjabinomorpha, Syngamus trachea, Cyathostoma bronchialis;Family Metastrongylidae such as Metastrongylus apri; Family Dictyocaulidae such as Dictyocaulus filaria, Dictyocaulus viviparus; Family Crenosomatidae such as Crenosoma aerophila, Crenosoma vulpis; Family Angiostrongylidae such as Angiostrongylus cantonensis, Angiostrongylus vasorum, Aelurostrongylus abstrusus; Family Filaroididae such as Filaroides hirthi, Filaroides osleri; Family Trichostrongylidae such as Trichostrongylus axei, Trichostrongylus colubriformis, Obeliscoides cuniculi; Family Haemonchidae such as Haemonchus contortus, Hyostrongylus rubidus, Mecistocirrus digitatus, Ostertagia ostertagi; Family Molineidae such as Nematodirus filicollis, Nematodirus spathiger; Family Oxyuridae such as Enterobius vermicularis, Oxyuris equi, Passalurus ambiguus; Family Heterakidae such as Heterakis gallinarum; Family Ascarididae such as Ascaris lumbricoides, Ascaris suum, Parascaris equorum; Family Toxocaridae such as Toxocara canis, Toxocara cati, Toxocara vitulorum; Family Anisakidae such as Anisakis spp.;Ascaridiidae such as Ascaridia galli; Gnathostomatidae such as Gnathostoma doloresi; Physalopteridae such as Physaloptera felidis and Physaloptera rara; Thelaziidae such as Thelazia callipaeda and Thelazia gulosa; Gongylonematidae such as Gongylonema pulchrum; Habronematidae such as Habronema majus, Habronema muscae, and Draschia megastoma; Dracunculidae such as Dracunculus medinensis; Spirocercidae such as Ascarops strongylina; Filariidae such as Stephanofilaria okinawaensis, Parafilaria multipapillosa, and Parafilaria bovicola; Setariidae such as Setaria digitata and Setaria equina; Onchocercidae such as Dirofilaria immitis, Brugia malayi, Onchocerca cervicalis, Onchocerca gibsoni, Dipetalonema reconditum, and Wuchereria bancrofti.;

[0045] Harmful arthropods such as harmful insects and harmful mites, and harmful nematodes may be harmful insects, harmful arthropods such as harmful mites, and harmful nematodes with reduced drug sensitivity or developed drug resistance to insecticides, acaricides, or nematicides.

[0046] As a method for controlling harmful arthropods or harmful nematodes of the present invention, an effective amount of the present compound or composition A is applied directly to the harmful arthropods or harmful nematodes and / or to the habitats (plants, soil, indoors, animals, etc.) of the harmful arthropods or harmful nematodes. Examples of the method for controlling harmful arthropods or harmful nematodes of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, fumigation treatment, water surface treatment, and seed treatment.

[0047] The present compound or composition A is usually mixed with an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc. and a surfactant, etc., and if necessary, formulation aids such as a binder, a dispersant, a stabilizer, etc. are added to prepare an aqueous suspension formulation, an oily suspension formulation, an oil formulation, an emulsion, an emulsion formulation, a microemulsion formulation, a microcapsule formulation, a wettable powder, a granular wettable powder, a dust, a granule, a tablet, an aerosol, a resin formulation, etc. It can be formulated and used not only in these formulations but also in the dosage forms described in Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers - 271~276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259 - 2517. These formulations usually contain the present compound or composition A in a weight ratio of 0.0001 to 99%.

[0048] Examples of the solid carrier include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powders and granules of chemical fertilizers (ammonium sulfate, superphosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0049] Examples of the liquid carrier include water, alcohols (such as ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (such as acetone, cyclohexanone, etc.), aromatic hydrocarbons (such as xylene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (such as hexane, cyclohexane, etc.), esters (such as ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (such as acetonitrile, etc.), ethers (such as ethylene glycol dimethyl ether, etc.), amides (such as N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (such as dimethyl sulfoxide, etc.), lactams (such as N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (such as oleic acid, etc.), and vegetable oils (such as soybean oil, etc.).

[0050] Examples of the gaseous carrier include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide gas.

[0051] Examples of the surfactant include nonionic surfactants (such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyethylene glycol fatty acid ester, etc.) and anionic surfactants (such as alkyl sulfonate, alkyl aryl sulfonate, alkyl sulfate, etc.).

[0052] Examples of other formulation adjuvants include binders, dispersants, colorants, stabilizers, etc. Specifically, for example, polysaccharides (such as starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (such as polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, and dibutylhydroxytoluene.

[0053] In the present invention, examples of the plant include the whole plant, stems and leaves, flowers, spikes, fruits, trunks, branches, canopies, seeds, vegetative reproductive organs, and seedlings.

[0054] The vegetative reproductive organ means an organ among the roots, stems, leaves, etc. of a plant that has the ability to grow when the part is separated from the main body and placed in the soil. Examples of vegetative reproductive organs include tuberous root, creeping root, bulb, corm (or solid bulb), tuber, rhizome, stolon, rhizophore, cane cuttings, propagule, and vine cutting. Note that stolons are sometimes called runners, propagules are also called bulbils, and are divided into broad buds and bulbils. Vine cutting means the shoots (a general term for leaves and stems) of sweet potatoes and yams, etc. Bulbs, corms, tubers, rhizomes, cane cuttings, rhizophores, or tuberous roots are collectively called bulbs. The cultivation of potatoes begins by planting tubers in the soil, and the tubers used are generally called seed potatoes.

[0055] As a method for controlling harmful arthropods or harmful nematodes by applying an effective amount of this compound or composition A to the soil, for example, there are methods such as applying an effective amount of this compound or composition A to the soil before or after planting plants, applying an effective amount of this compound or composition A to the rhizosphere of crops to be protected from damage such as feeding by harmful arthropods or harmful nematodes, and allowing an effective amount of this compound or composition A to penetrate and migrate into the plant body from the roots or the like to control harmful arthropods or harmful nematodes that feed on the plants. More specifically, for example, hole treatment (hole spraying, hole treatment soil mixing), base treatment (base spraying, base soil mixing, base perfusion, base treatment in the latter half of the seedling raising period), furrow treatment (furrow spraying, furrow soil mixing), ridging treatment (ridging spraying, ridging soil mixing, ridging spraying during the growth period), ridging treatment at sowing (ridging spraying at sowing, ridging soil mixing at sowing), overall treatment (overall soil spraying, overall soil mixing), side ridging treatment, water surface treatment (water surface application, water surface application after flooding), other soil spraying treatments (granule foliar spraying during the growth period, spraying under the canopy or around the main trunk, soil surface spraying, soil surface mixing, hole sowing spraying, surface spraying of the ridge part, inter-plant spraying), other perfusion treatments (soil perfusion, seedling raising period perfusion, chemical solution injection treatment, ground level perfusion, chemical drip irrigation, chemigation), seedling box treatment (seedling box spraying, seedling box perfusion, seedling box chemical solution flooding), seedling tray treatment (seedling tray spraying, seedling tray perfusion, seedling tray chemical solution flooding), seedbed treatment (seedbed spraying, seedbed perfusion, water seedling replacement seedbed spraying, seedling dipping), bed soil mixing treatment (bed soil mixing, bed soil mixing before sowing, spraying before covering soil at sowing, spraying after covering soil at sowing, covering soil mixing), and other treatments (hill soil mixing, hoeing in, topsoil mixing, soil mixing in the rainwater runoff part, planting position treatment, granule inflorescence spraying, paste fertilizer mixing).

[0056] Examples of seed treatment include treating the seeds or vegetative reproductive organs with the present compound or Composition A. Specifically, for example, a spraying treatment in which a suspension of the present compound or Composition A is atomized and sprayed onto the seed surface or the vegetative reproductive organ surface, a coating treatment in which the present compound or Composition A is applied to the seeds or vegetative reproductive organs, a dipping treatment in which the seeds or vegetative reproductive organs are immersed in a chemical solution of the present compound or Composition A for a certain period of time, and a method of coating the seeds or vegetative reproductive organs with a carrier containing the present compound or Composition A (film coating treatment, pellet coating treatment, etc.). Among the above-mentioned vegetative reproductive organs, seed tubers are particularly mentioned. When treating seeds or vegetative reproductive organs with Composition A, Composition A can be treated as a single formulation on the seeds or vegetative reproductive organs, or Composition A can be treated on the seeds or vegetative reproductive organs in multiple times as different multiple formulations. Examples of the method of treating Composition A in multiple times as different multiple formulations include, for example, treating with a formulation containing only the present compound as the active ingredient, air-drying the seeds or vegetative reproductive organs, and then treating with a formulation containing this component; and treating with a formulation containing the present compound and this component as the active ingredient, air-drying the seeds or vegetative reproductive organs, and then treating with a formulation containing this component other than the treated this component. The seeds or vegetative reproductive organs holding the present compound or Composition A in the present invention mean those in a state where the present compound or Composition A is attached to the surface of the seeds or vegetative reproductive organs. The above-mentioned seeds or vegetative reproductive organs holding the present compound or Composition A may have other materials attached before and after the present compound or Composition A is attached to the seeds or vegetative reproductive organs. In addition, when Composition A adheres to the surface of the seeds or vegetative reproductive organs as a layer, the layer may consist of one layer or multiple layers. When consisting of multiple layers, each layer may be a layer containing one or more active ingredients, or may consist of a layer containing one or more active ingredients and a layer not containing active ingredients. The seeds or vegetative reproductive organs holding the present compound or Composition A can be obtained, for example, by applying a formulation containing the present compound or Composition A to the seeds or vegetative reproductive organs by the above-mentioned seed treatment method.

[0057] When the present compound or composition A is used for controlling harmful arthropods or harmful nematodes in the agricultural field, the application rate is usually 1 to 10,000 g in terms of the amount of the present compound per 10,000 m 2 ². When treating seeds or vegetative reproductive organs, the amount of the present compound is usually applied in the range of 0.001 to 100 g per 1 kg of seeds or vegetative reproductive organs. When the present compound or composition A is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.01 to 10,000 ppm and then applied, while granules, powders, etc. are usually applied as they are.

[0058] In addition, the present compound or composition A can also be treated by methods such as winding a resin preparation processed into a sheet or string shape around a crop, stretching it near the crop, or laying it on the soil at the base of the plant.

[0059] When the present compound or composition A is used for controlling harmful arthropods inhabiting indoors, the application rate is usually 0.01 to 1000 mg in terms of the amount of the present compound per 1 m 2 ² of the treatment area when treating the surface, and usually 0.01 to 500 mg in terms of the amount of the present compound per 1 m 3 ³ of the treatment space when treating the space. When the present compound or composition A is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.1 to 10,000 ppm and then applied, while oil agents, aerosol agents, fumigants, bait agents, etc. are applied as they are.

[0060] When the present compound or composition A is used for controlling harmful arthropods or harmful nematodes parasitic on domestic animals such as cows, horses, pigs, sheep, goats, chickens, etc., or small animals such as dogs, cats, rats, mice, etc., it can be used on animals by a method known in veterinary medicine. Specific methods of use include, for example, oral administration by mixing into tablets, capsules, chewable tablets, feeds, etc., administration by suppositories and injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), spraying, coating, dripping treatment with oil agents, aqueous solutions, spot-on agents, pour-on agents, shampoos, lotions, pastes, etc., or a method of processing resin preparations into collars, ear tags, bracelets, and clothing for wearing. The amount of the present compound when administered to animals is usually in the range of 0.1 to 1000 mg per 1 kg of the animal's body weight.

[0061] Further, the present compound or composition A can be used as a control agent for harmful arthropods or harmful nematodes in agricultural fields such as fields, paddy fields, lawns, orchards, etc. Examples of plants include the following.

[0062] Maize (dent, flint, soft, pop, waxy, sweet, field corn), rice (long grain, short grain, medium grain, japonica, tropical japonica, indica, javanica, paddy, upland, floating, direct seeding, transplanting, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, each winter wheat type, spring wheat type), barley (two-row barley (= beer barley), six-row barley, naked barley, glutinous barley, each winter barley type, spring barley type), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oats type, spring oats type), sorghum, cotton (upland variety, pima variety), soybean (fully mature seed harvest variety, edamame variety, green forage variety, each indeterminate growth type, determinate growth type, semi-determinate growth type), peanut, buckwheat, sugar beet (for sugar production, for feed, root vegetable, leaf vegetable, fuel), rapeseed (winter rapeseed type, spring rapeseed type), sunflower (for oil extraction, for food, for ornamental), sugarcane, tobacco, camphor tree, mulberry, Solanaceae vegetables (eggplant, tomato, pepper, capsicum, potato, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard spinach, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, shungiku, artichoke, lettuce, etc.), Alliaceae vegetables (green onion, onion, garlic, asparagus, etc.), Apiaceae vegetables (carrot, parsley, celery, American lovage, etc.), Chenopodiaceae vegetables (spinach, lamb's quarters, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, pomaceous fruits (apple, pear, Japanese pear, Chinese pear, quince, membrillo, etc.), stone fruits (peach, plum, nectarine, apricot, almond, plumcot, prune, etc.), citrus fruits (satsuma mandarin, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashew nut, macadamia nut, etc.), berry fruits (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster mushroom, fig, olive, loquat, banana, coffee, date palm, coconut palm, ornamental plants, forest plants, grasses,Forage grasses.

[0063] The above plants are not particularly limited as long as they are commonly cultivated varieties. The above plants include plants that can be produced by natural crossing, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants imparted with resistance to HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazetapyr and thifensulfuron-methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, herbicides such as bromoxynil or dicamba; plants capable of synthesizing selective toxins such as those known in the genus Bacillus like Bacillus thuringiensis; plants that can synthesize gene fragments partially matching endogenous genes derived from harmful insects and impart specific insecticidal activity by inducing gene silencing (RNAi; RNA interference) in the target harmful insect body.

Example

[0064] Hereinafter, the present invention will be described in more detail by production examples, formulation examples, test examples, etc., but the present invention is not limited only to these examples.

[0065] Compounds 1 to 3 of the present invention were obtained according to the methods for obtaining norzomantamine, zomantamine, and norzomantaminone in Reference Example 1 of the Examples in the specification of JP-A-10-53589. Compound 4 of the present invention was isolated according to the method for obtaining zomantaminone described in Heterocyclic Communications, 1995, 1(2-3), 207-214.

[0066] Production Example 1 Compound 1 of the present invention was obtained according to Reference Example 1 of the Examples in the specification of JP-A-10-53589. The 1H-NMR data of the obtained Compound 1 is as follows. 1 is as follows. 1 1H-NMR (CDCl3) δ (ppm): 0.91 (3H, d, J = 6.6 Hz), 1.01 (6H, s), 1.09 (1H, dd, J = 13 Hz, 12 Hz), 1.16 (3H, s), 1.43 - 1.60 (3H, m), 1.66 - 1.79 (2H, m), 1.88 - 1.92 (1H, m), 1.92 (1H, d, J = 14 Hz), 2.02 (3H, s), 2.09 (1H, dd, J = 13 Hz, 4.7 Hz), 2.16 (1H, d, J = 14 Hz), 2.19 - 2.25 (4H, m), 2.37 (1H, d, J = 20 Hz), 2.51 (1H, dd, J = 14 Hz, 12 Hz), 2.64 - 2.72 (2H, m), 2.84 (1H, s), 3.23 (1H, t, J = 6.1 Hz), 3.28 (1H, d, J = 6.1 Hz), 3.67 (1H, d, J = 20 Hz), 4.55 - 4.56 (1H, m), 5.92 (1H, s).

[0067] Production Example 2 This Compound 2 was obtained according to Reference Example 1 in the Examples of the specification of JP-A-10-53589. The 1 1H-NMR data of the obtained Compound 2 are as follows. 1 1H-NMR (CDCl3) δ (ppm): 0.92 (3H, d, J = 6.4 Hz), 0.98 (3H, s), 1.00 (3H, s), 1.10 (1H, dd, J = 13 Hz, 12 Hz), 1.17 (3H, d, J = 6.9 Hz), 1.20 (3H, s), 1.47 - 1.59 (3H, m), 1.66 - 1.81 (2H, m), 1.87 - 1.91 (1H, m), 1.92 (1H, d, J = 14 Hz), 2.01 (3H, s), 2.10 (1H, dd, J = 13 Hz, 4.9 Hz), 2.17 (1H, d, J = 14 Hz), 2.17 - 2.30 (3H, m), 2.37 (1H, d, J = 20 Hz), 2.38 - 2.46 (1H, m), 2.66 (1H, dd, J = 13 Hz, 5.5 Hz), 2.99 - 3.04 (1H, m), 3.22 (1H, s), 3.25 (1H, d, J = 6.9 Hz), 3.29 (1H, d, J = 6.9 Hz), 3.67 (1H, d, J = 20 Hz), 4.54 - 4.57 (1H, m), 5.92 (1H, s).

[0068] Production Example 3 This Compound 3 was obtained according to Reference Example 1 of the Examples in the specification of JP-A-10-53589. The 1 1H-NMR data of the obtained Compound 3 are as follows. 1 1H-NMR (CDCl3) δ (ppm): 0.90 (3H, d, J = 6.4 Hz), 1.02 (3H, s), 1.07 (3H, s), 1.11 (1H, d, J = 12 Hz), 1.28 (3H, s), 1.41 - 1.48 (1H, m), 1.53 - 1.61 (2H, m), 1.76 - 1.88 (3H, m), 1.97 (1H, dd, J = 12 Hz, 5.2 Hz), 2.03 (3H, s), 2.21 - 2.32 (2H, m), 2.49 - 2.76 (4H, m), 2.55 (1H, d, J = 21 Hz), 2.97 (1H, s), 3.03 (1H, d, J = 8.4 Hz), 3.36 (1H, dd, J = 18 Hz, 3.4 Hz), 3.99 (1H, dd, J = 8.4 Hz, 6.8 Hz), 4.13 (1H, d, J = 21 Hz), 4.53 (1H, d, J = 6.8 Hz), 5.91 (1H, s).

[0069] Production Example 4 This Compound 4 was obtained according to the method for obtaining zoantamine described in Heterocyclic Communications, 1995, 1(2 - 3), 207 - 214. The 1 1H-NMR data of the obtained Compound 4 are as follows. 11H-NMR (CDCl3) δ (ppm): 0.90 (3H, d, J = 6.6 Hz), 0.99 (3H, s), 1.02 - 1.07 (1H, m), 1.10 (3H, s), 1.17 (3H, d, J = 6.8 Hz), 1.25 (3H, s), 1.45 - 1.89 (6H, m), 2.00 (1H, dd, J = 14 Hz, 4.8 Hz), 2.03 (3H, s), 2.14 (1H, dd, J = 18 Hz, 11 Hz), 2.26 - 2.32 (1H, m), 2.55 (1H, d, J = 20 Hz), 2.61 (1H, dd, J = 14 Hz, 5.4 Hz), 2.82 (1H, ddd, J = 14 Hz, 11 Hz, 3.9 Hz), 2.98 - 3.03 (2H, m), 3.27 (1H, dd, J = 18 Hz, 3.9 Hz), 3.36 (1H, s), 4.01 (1H, dd, J = 8.0 Hz, 7.0 Hz), 4.11 (1H, d, J = 20 Hz), 4.53 (1H, d, J = 7.0 Hz), 5.90 (1H, s).

[0070] Production Example 5 This compound 5 was obtained according to Reference Example 2 in the Examples of the specification of JP-A-10-53589. The 1 1H-NMR data of the obtained compound 5 are as follows. 1 1H-NMR (CD3OD) δ (ppm): 1.02 (3H, s), 1.03 (3H, d, J = 7.4 Hz), 1.36 (3H, s), 1.49 (3H, s), 1.49 (1H, t, J = 13 Hz), 1.64 - 1.71 (1H, m), 1.82 (1H, d, J = 15 Hz), 1.90 - 1.99 (3H, m), 2.03 (1H, d, J = 15 Hz), 2.07 (3H, s), 2.32 (1H, d, J = 14 Hz), 2.47 - 2.76 (8H, m), 2.92 (1H, d, J = 16 Hz), 3.16 (1H, d, J = 16 Hz), 3.33 (1H, d, J = 15 Hz), 3.34 (1H, s), 4.26 (1H, dd, J = 13 Hz, 6.5 Hz), 4.38 (1H, d, J = 13 Hz), 4.95 - 4.97 (1H, m), 5.93 (1H, s).

[0071] Production Example 6 This compound 6 was produced as follows. To a 2.5 mL methanol solution of 25.5 mg of zoantamine, 15 drops of 1.2 N hydrochloric acid were added, and the mixture was stirred at room temperature for 1 hour. The resulting solution was concentrated under reduced pressure to obtain 28.5 mg of Compound 6. The obtained Compound 6 1 The 1H-NMR data are as follows. 1 1H-NMR (CD3OD) δ (ppm): 1.01 (3H, s), 1.04 (3H, d, J = 6.3 Hz), 1.20 (3H, d, J = 7.0 Hz), 1.34 (3H, s), 1.53 (3H, s), 1.47 - 1.54 (1H, m), 1.68 (1H, ddd, J = 14 Hz, 12 Hz, 2.3 Hz), 1.84 (1H, dd, J = 15 Hz, 3.5 Hz), 1.81 - 2.03 (3H, m), 1.98 (1H, d, J = 15 Hz), 2.07 (3H, s), 2.33 (1H, dt, J = 14 Hz, 3.5 Hz), 2.43 - 2.46 (2H, m), 2.54 - 2.61 (2H, m), 2.73 (1H, dd, J = 14 Hz, 5.3 Hz), 2.90 - 2.97 (2H, m), 3.05 (1H, dq, J = 7.0 Hz, 5.3 Hz), 3.20 (1H, d, J = 15 Hz), 3.36 (1H, s), 3.39 (1H, d, J = 15 Hz), 4.29 (1H, dd, J = 13 Hz, 6.2 Hz), 4.38 (1H, d, J = 13 Hz), 4.96 - 4.97 (1H, m), 5.94 (1H, s).

[0072] Next, formulation examples of this compound are shown. Here, "parts" represent parts by weight. Also, Compound S represents the compounds of Compound 1 to Compound 40.

[0073] Formulation Example 1 A mixture of polyoxyethylene alkyl ether sulfate ammonium salt and silica (weight ratio 1:1), 35 parts, any one of Compound S, 10 parts, and water, 55 parts, are mixed and finely pulverized by a wet pulverization method to obtain a formulation.

[0074] Formulation Example 2 Any one of Compound S, 50 parts, calcium lignin sulfonate, 3 parts, sodium lauryl sulfate, 2 parts, and silica, 45 parts, are pulverized and mixed to obtain a formulation.

[0075] Formulation Example 3 A formulation is obtained by mixing 5 parts of any one of the present compounds S, 9 parts of polyoxyethylene styryl phenyl ether, 5 parts of polyoxyethylene decyl ether (number of added ethylene oxides: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene.

[0076] Formulation Example 4 A formulation is obtained by pulverizing and mixing 2 parts of any one of the present compounds S, 1 part of silica, 2 parts of calcium lignosulfonate, 30 parts of bentonite, and 65 parts of kaolin clay, adding an appropriate amount of water, kneading, granulating with a granulator, and then drying.

[0077] Formulation Example 5 10 parts of any one of the present compounds S is mixed with a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO, and 6.3 parts of GERONOL (registered trademark) TE250, 2.7 parts of Ethylan (registered trademark) NS-500LQ, and 54 parts of solvent naphtha are added thereto and mixed to obtain a formulation.

[0078] Formulation Example 6 0.1 part of any one of the present compounds S and 39.9 parts of kerosene are mixed and dissolved, placed in an aerosol container, and filled with 60 parts of liquefied petroleum gas (a mixture of propane, butane, and isobutane; saturated vapor pressure: 0.47 MPa (25 °C)) to obtain a formulation.

[0079] Formulation Example 7 0.2 part of any one of the present compounds S, 50 parts of pyrethrum extract meal powder, 30 parts of tab powder, and 19.8 parts of wood powder are mixed, an appropriate amount of water is added and kneaded, then extruded into a plate-shaped sheet and made into a spiral shape with a punching machine to obtain a formulation.

[0080] Next, the efficacy of the present compound against harmful arthropods and harmful nematodes is shown by test examples. In the following test examples, the tests were carried out at 25 °C. Also, the untreated plot means a plot where the same operations as the treated plot are carried out except that the test compound is not used.

[0081] Test method 1 The test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Sindain (registered trademark) is added thereto to prepare a dilution containing the test compound at a predetermined concentration. The dilution is sprayed onto cabbage (Brassicae oleracea) seedlings (at the stage of the 3rd - 4th true leaf expansion) planted in a container at a rate of 20 mL / seedling. Then, 10 third - instar larvae of Spodoptera litura are released. Six days later, the number of surviving insects is counted, and the mortality rate is calculated from the following formula. Mortality rate (%) = (1 - number of surviving insects / 10) × 100

[0082] Test Example 1 - 1 When the predetermined concentration was set at 200 ppm and the following compounds of the present invention were used as test compounds and the test was conducted according to Test Method 1, all of the following compounds of the present invention showed a mortality rate of 100%. Compounds of the present invention: 1, 2, 5, 6

[0083] Test method 2 The test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Sindain (registered trademark) is added thereto to prepare a dilution containing the test compound at a predetermined concentration. The dilution is sprayed onto cabbage (Brassicae oleracea) seedlings (at the stage of the 3rd - 4th true leaf expansion) planted in a container at a rate of 20 mL / seedling. Then, 10 third - instar larvae of Plutella xylostella are released. Six days later, the number of surviving insects is counted, and the mortality rate is calculated from the following formula. Mortality rate (%) = (1 - number of surviving insects / 10) × 100

[0084] Test Example 2 - 1 When the predetermined concentration was set at 200 ppm and the following compounds of the present invention were used as test compounds and the test was conducted according to Test Method 2, all of the following compounds of the present invention showed a mortality rate of 100%. Compounds of the present invention: 1, 2, 5, 6

[0085] Test Example 2 - 2 Instead of Preparation Example 5, Preparation Example 1 was used, the predetermined concentration was set at 500 ppm, and the following compound of the present invention was used as the test compound. As a result of conducting the test according to Test Method 2, the following compound of the present invention showed a mortality rate of 80%. Compound of the present invention: 4

[0086] Test Method 3 The test compound is formulated according to the method described in Preparation Example 5, and water containing 0.03% by volume of Sindain (registered trademark) is added thereto to prepare a dilution containing the test compound at a predetermined concentration. Approximately 30 aphids (all stages) are inoculated onto cucumber (Cucumis sativus) seedlings (second true leaf expansion stage) planted in a container. One day later, this dilution is sprayed onto the seedlings at a rate of 10 mL / seedling. After another 5 days, the number of surviving insects is investigated, and the control value is determined by the following formula. Control value (%) = {1 - (Cb × Tai) / (Cai × Tb)} × 100 In addition, the letters in the formula represent the following meanings. Cb: Number of test insects in the untreated plot Cai: Number of surviving insects at the time of investigation in the untreated plot Tb: Number of test insects in the treated plot Tai: Number of surviving insects at the time of investigation in the treated plot

[0087] Test Example 3-1 With the predetermined concentration set at 200 ppm and the following compounds of the present invention used as test compounds, and the test conducted according to Test Method 3, all of the following compounds of the present invention showed a control value of 90% or more. Compound of the present invention: 1, 2, 5, 6

[0088] Test Method 4 The test compound is formulated according to the method described in Preparation Example 5, and water is added thereto to prepare a dilution containing the test compound at a predetermined concentration. The dilution is perfusion-injected at the base of the plant at a rate of 5 mL / seedling onto cucumber seedlings (second true leaf expansion stage) planted in a container. Seven days later, approximately 30 aphids (all stages) are inoculated onto the leaf surface of this seedling. After another 6 days, the number of surviving insects is investigated, and the control value is determined by the following formula. Control value (%) = {1 - (Cb × Tai) / (Cai × Tb)} × 100 In addition, the characters in the formula represent the following meanings. Cb: Number of test insects in the untreated plot Cai: Number of surviving insects at the time of investigation in the untreated plot Tb: Number of test insects in the treated plot Tai: Number of surviving insects at the time of investigation in the treated plot

[0089] Test Example 4-1 With the predetermined concentration set at 200 ppm, using the following present compounds as test compounds and conducting tests according to Test Method 4, all of the following present compounds showed a control value of 90% or more. Present compounds: 1, 2, 5, 6

[0090] Test Method 5 Prepare the test compound as a formulation according to the method described in Formulation Example 5, add water containing 0.03% by volume of Sindain (registered trademark) thereto, and prepare a dilution containing the test compound at a predetermined concentration. Spray the dilution on rice (Oryza sativa) seedlings (at the second leaf unfolding stage) planted in a container at a rate of 10 mL / seedling. Then, release 20 third-instar larvae of the small brown planthopper. After 6 days, investigate the number of surviving insects and calculate the mortality rate according to the following formula. Mortality rate (%) = {1 - number of surviving insects / 20} × 100

[0091] Test Example 5-1 With the predetermined concentration set at 200 ppm, using the following present compounds as test compounds and conducting tests according to Test Method 5, all of the following present compounds showed a mortality rate of 100%. Present compounds: 1, 2, 5, 6

[0092] Test Method 6 Prepare the test compound as a formulation according to the method described in Formulation Example 5, add water thereto, and prepare a dilution containing the test compound at a predetermined concentration. Add 5 mL of the dilution to a container, and place rice (Oryza sativa) seedlings (at the second leaf unfolding stage) planted in a container with holes in the bottom into it. After 7 days, release 20 third-instar larvae of the small brown planthopper. After another 6 days, investigate the number of surviving insects and calculate the mortality rate according to the following formula. Mortality rate (%) = {1 - Number of surviving insects / 20} × 100

[0093] Test Example 6-1 With the specified concentration set at 200 ppm, when the following compounds of the present invention were used as test compounds and tested according to Test Method 6, all of the following compounds of the present invention showed a mortality rate of 90% or more. Compounds of the present invention: 1, 2, 5, 6

[0094] Test Method 7 The test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Sindain (registered trademark) is added thereto to prepare a dilution containing the test compound at a specified concentration. The dilution is sprayed onto cabbage (Brassicae oleracea) seedlings (at the second true leaf unfolding stage) planted in a container at a rate of 10 mL / seedling. Thereafter, the second true leaf is cut off and placed in the container, and about 20 larvae of the citrus red mite are released therein. After 6 days, the number of surviving insects is investigated, and the mortality rate is determined by the following formula. Mortality rate (%) = {1 - Number of surviving insects / 20} × 100

[0095] Test Example 7-1 With the specified concentration set at 200 ppm, when the following compounds of the present invention were used as test compounds and tested according to Test Method 7, all of the following compounds of the present invention showed a mortality rate of 90% or more. Compounds of the present invention: 1, 2, 5, 6

[0096] Test Method 8 The test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Sindain (registered trademark) is added thereto to prepare a dilution containing the test compound at a specified concentration. Adult tobacco whiteflies are released onto tomato (Lycopersicon esculentum) seedlings planted in a container to lay eggs for about 24 hours. The seedlings are stored for 8 days to hatch larvae from the laid eggs. The dilution is sprayed onto these seedlings at a rate of 10 mL / seedling. After 7 days, the number of surviving insects is investigated, and the control value is determined by the following formula. Control value (%) = {1 - (Cb × Tai) / (Cai × Tb)} × 100 Note that the characters in the formula represent the following meanings. Cb: Number of insects just before treatment in the untreated plot Cai: Number of surviving insects at the time of investigation in the untreated plot Tb: Number of insects just before treatment in the treated plot Tai: Number of surviving insects at the time of investigation in the treated plot

[0097] Test Example 8-1 With the predetermined concentration set at 200 ppm and the following compounds of the present invention used as test compounds, tests were conducted according to Test Method 8. As a result, all of the following compounds of the present invention showed a control value of 90% or more. Compounds of the present invention: 1, 2, 5, 6

[0098] Test Method 9 The test compound is formulated according to the method described in Formulation Example 1, water is added thereto, and a dilution containing the test compound at a predetermined concentration is prepared. Thirty last-instar larvae of Aedes aegypti are released into the dilution, and the state of the Aedes aegypti larvae is investigated after one day to determine the mortality rate. The mortality rate is calculated by the following formula. Mortality rate (%) = (Number of dead insects / Number of test insects) × 100

[0099] Test Example 9-1 With the predetermined concentration set at 3.5 ppm and the following compounds of the present invention used as test compounds, tests were conducted according to Test Method 9. As a result, all of the following compounds of the present invention showed a mortality rate of 100%. Compounds of the present invention: 1, 2, 3, 4

[0100] Test Method 10 The test compound is dissolved in acetone containing a surfactant and then poured into a container with an internal volume of 20 mL, and the inner surface of the container is uniformly coated so that the test compound is 10 mg / m 2 and the surfactant is 40 mg / m 2 and then dried. Five female adult Aedes aegypti are placed in the container and the lid is closed. After a predetermined time has elapsed, the state of the Aedes aegypti is investigated to determine the mortality rate. The mortality rate is calculated by the following formula. Mortality rate (%) = (Number of dead insects / Number of test insects) × 100

[0101] Test Example 10-1 The results of the test conducted according to Test Method 10 are shown below. Assuming the predetermined time is 1 day and using the following present compounds as test compounds, all of the following present compounds showed a 100% mortality rate. Present compounds: 1, 2, 5, 6

[0102] Test Method 11 After dissolving the test compound in acetone containing a surfactant, pour it into a container with an internal volume of 20 mL, and uniformly coat the inner surface of the container so that the test compound is 20 mg / m 2 and the surfactant is 40 mg / m 2 Then dry it. Put 10 adult cat fleas into the container and close the lid. After a predetermined time has elapsed, investigate the state of the cat fleas and determine the mortality rate. The mortality rate is calculated by the following formula. Mortality rate (%) = (Number of dead insects / Number of test insects) × 100

[0103] Test Example 11-1 The results of the test conducted according to Test Method 11 are shown below. Assuming the predetermined time is 2 days and using the following present compounds as test compounds, all of the following present compounds showed a 100% mortality rate. Present compounds: 1, 2

[0104] Test Example 12 After dissolving 60 mg of Present Compound 1 or 2 in 600 μL of acetone containing 5% Tween 20, add water to this to prepare a 60 mL solution. Mix 20 mL of this solution with 400 mL of soil contaminated with sweet potato white grubs, and transplant the roots of healthy tomato seedlings (3 - 4 leaf stage) into this soil. Immediately after transplantation, irrigate the remaining 40 mL of this solution into the soil of the tomato seedlings. After 28 days, pull out the roots from the soil, wash them with water, and investigate the root damage degree (root knot degree) according to Zeck's root knot index (Zeck, W. M. (1971): Pflanzenschutz-Nachichten. Bayer AG, 24, 141 - 144.). As a result, the root knot index in the treatment groups of Compounds 1 and 2 was "2". On the other hand, the root knot index in the non-treatment group was "5". From the above, Compounds 1 and 2 reduced root knot formation. Zeck's root knot index 0: No root knots are observed at all. 1: By careful observation, several small root knots can be recognized. 2: The same several small root knots as in 1 can be easily confirmed. 3: There are many small root knots, and some of them are fused. The root function is hardly impaired. 4: There are many small root knots and several large root knots. Most of the roots are functioning. 5: Root knots are significantly formed on 25% of the roots and are not functioning. 6: Root knots are significantly formed on 50% of the roots and are not functioning. 7: Root knots are significantly formed on 75% of the roots, and the root regeneration ability is also lost. 8: There are no healthy roots, and the nutrient absorption of the plant is inhibited. The stems and leaves are still green. 9: The root system completely covered with root knots is rotting. The plant is dying. 10: The plant and the roots are dead.

Industrial Applicability

[0105] This compound exhibits excellent control effects against harmful arthropods or harmful nematodes.

Claims

1. Formula (I) 【Chemical 1】 〔wherein, R １ represents a hydrogen atom or a methyl group, R ２ and R ３ each represents a hydrogen atom, or R ２ and R ３ together represent an oxo group. ]] A method for controlling harmful arthropods or harmful nematodes, which comprises applying an effective amount of the compound represented by, or an N-oxide thereof or a salt thereof, to the harmful arthropods or harmful nematodes or the habitats of harmful arthropods or harmful nematodes.

2. In formula (I), R ２ and R ３ are each a hydrogen atom, the method according to claim 1.

3. Formula (I) 【Chemical 2】 〔wherein, R １ represents a hydrogen atom or a methyl group, R ２ and R ３ each represents a hydrogen atom, or R ２ and R ３ together represent an oxo group.]] A composition for controlling harmful arthropods or harmful nematodes, which contains the compound represented by, or an N-oxide thereof or a salt thereof.

4. The composition according to claim 3, further comprising one or more components selected from the group consisting of group (a), group (b), group (c), group (d), and group (e): Group (a): a group consisting of an insecticidal active ingredient, a acaricidal active ingredient, and a nematicidal active ingredient; Group (b): a bactericidal active ingredient; Group (c): a plant growth regulating ingredient; Group (d): a repellent ingredient; Group (e): a biological control material.

5. A method for controlling harmful arthropods or harmful nematodes, which comprises applying an effective amount of the composition according to claim 4 to the harmful arthropods or harmful nematodes or the habitats of harmful arthropods or harmful nematodes.

6. Formula (I) 【Chemical Formula 3】 〔wherein, R １ represents a hydrogen atom or a methyl group, R ２ and R ３ each represents a hydrogen atom, or R ２ and R ３ together represent an oxo group.]] Seeds or vegetative reproductive organs holding an effective amount of the compound represented by, or an N-oxide thereof or a salt thereof, or an effective amount of the composition according to claim 4.

7. Formula (I) 【Chemical Formula 4】 〔wherein, R １ represents a hydrogen atom or a methyl group, R ２ and R ３ each represents a hydrogen atom, or R ２ and R ３ together represent an oxo group. ]] A composition for controlling harmful arthropods or harmful nematodes, which contains the compound represented by, or an N-oxide thereof or a salt thereof, and an inert carrier.

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