Pest control agents

Abstract

To provide a compound having high pest control activity and high practicability.SOLUTION: Compounds represented by a formula (1) or a formula (2) or a formula (3) or salts thereof or N-oxides thereof are provided.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a compound represented by formula (1), formula (2) or formula (3), or a salt thereof, or an N-oxide thereof, and a pest control agent comprising the compound represented by formula (1), formula (2) or formula (3) as an active ingredient. [Background technology]

[0002] Various compounds have been studied and put to practical use for the purpose of controlling harmful arthropods. For example, Patent Documents 1 and 2 disclose condensed heterocyclic compounds as pest control agents. Patent Documents 3 and 4 claim to include 2-(pyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyridine, but have not actually been synthesized. Patent Document 5 discloses a compound having a certain [1,2,4]triazolo[1,5-a]pyridine ring as a pest control agent. Patent Document 6 discloses a certain amide compound. However, no compound has been found that has high pest control activity and is highly practical. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2009 / 131237 [Patent Document 2] International Publication No. 2013 / 180194 [Patent Document 3] International Publication No. 2013 / 191113 [Patent Document 4] International Publication No. 2015 / 000715 [Patent Document 5] Patent Publication No. 2018-24657 [Patent Document 6] International Publication No. 2015 / 068719 Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present invention is to provide a novel compound exhibiting excellent control activity against various pests, and a pest control agent containing the compound as an active ingredient. [Means for solving the problem]

[0005] As a result of extensive research, the present inventors have found that the compounds represented by formula (1), (2) or (3) have high pest control activity, and have completed the present invention.

[0006] That is, the present invention relates to, but is not limited to, the following: <1> A compound represented by formula (1), (2), or (3), or a salt thereof, or an N-oxide thereof: [In formula (1), formula (2) and formula (3), [ka] G 1 is G 1 -1, G 1 -2, G 1 -3, G 1 -4 or G 1 -5 represents the structure represented by [ka] G 2 is G 2 -1, G 2 -2, G 2 -3, G 2 -4 or G 2 -5 represents the structure represented by [ka] R 1 , R 2 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, or C 1 ~C 6 Alkyl, halo(C 1 ~C 6) Alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 )Alkoxy, halo(C 1 ~C 6 ) Alkylthio, Halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) alkylsulfonyl, (C=O)NY 1 Y 2 Or -NY 1 Y 2 represents A 1 CR C or N, A 2 CR E or N, where A 1 , A 2 One of them is N and the other is CR C or CR E It is.) R A , R B , R C , R D and R E are each independently a hydrogen atom, a halogen atom, or C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 3 ~C 6 Cycloalkyl, substituted by U (C 3 ~C 6 ) Cycloalkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) alkoxy, a phenoxy group optionally substituted with up to five Z; 1 ~C 6 Alkylthio, halo(C 1 ~C 6 ) Alkylthio, C 1 ~C 6 Alkyl sulfinyl, halo(C 1 ~C 6 ) alkylsulfinyl, C1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylsulfonyl, (C=O)NY 3 Y 4 , -NY 3 Y 4 , cyano, nitro, a phenyl group which may be substituted with up to five Z's, a pyridyl group which may be substituted with up to four Z's, a pyrimidyl group which may be substituted with up to three Z's, a pyrazyl group which may be substituted with up to three substituents, a pyridazyl group which may be substituted with up to three Z's, a thienyl group which may be substituted with up to three Z's, a furanyl group which may be substituted with up to three Z's, or V; V represents a structure represented by V-1, V-2, V-3, V-4, V-5 or V-6; [ka] Z is independently a hydrogen atom, a halogen atom, or C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, halo(C 1 ~C 6 ) Alkylthio, C 1 ~C 6 Alkyl sulfinyl, halo(C 1 ~C 6 ) alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylsulfonyl, -NY 5 Y 6 , cyano or nitro; Q2, Q3 or Q4 represents the number of substituents of Z; Q2 represents an integer of 0, 1 or 2; Q3 represents an integer of 0, 1, 2 or 3; Q4 represents an integer of 0, 1, 2, 3 or 4; When Q2, Q3 or Q4 represents an integer of 2 or more, multiple Z's may be the same or different from each other; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 are each independently a hydrogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkylcarbonyl, halo(C 1 ~C 6 ) Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, halo(C 1 ~C 6 ) alkoxycarbonyl, C 1 ~C 6 Alkyl sulfonyl or halo(C 1 ~C 6 ) alkylsulfonyl; U is cyano, -C(O)OH or -C(O)NH 2 represents D is a hydrogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkyl carbonyl, C 3 ~C 6 Cycloalkylcarbonyl, halo(C 1 ~C 6 ) Alkylcarbonyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) Alkyl sulfonyl, C 1 ~C 3 Alkyloxycarbonyl, halo(C 1 ~C 3 ) alkyloxycarbonyl, benzenecarbonyl which may be substituted by up to five T; T is independently a hydrogen atom, a halogen atom, or C 1 ~C 3 Alkyl, halo(C 1 ~C 3 ) Alkyl, C 1 ~C 3 Alkoxy, halo(C 1 ~C 3 ) alkoxy, E is a hydrogen atom, C 1 ~C 6 Alkyl, cyclopropylmethyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkyl carbonyl, C 3 ~C 6 Cycloalkylcarbonyl, halo(C 1 ~C 6 ) Alkylcarbonyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl. <2> A compound represented by formula (1), (2), or (3), or a salt thereof, or an N-oxide thereof: [In formula (1), formula (2) and formula (3), [ka] G 1 is G 1 -1, G 1 -2, G 1 -3, G 1 -4 or G 1 -5 represents the structure represented by [ka] G 2 is G 2 -1, G 2 -2, G 2 -3, G 2 -4 or G 2-5 represents the structure represented by [ka] R 1 , R 2 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, or C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 )Alkoxy, halo(C 1 ~C 6 ) Alkylthio, Halo(C 1 ~C 6 ) alkylsulfinyl or halo(C 1 ~C 6 ) alkylsulfonyl; A 1 CR C or N, A 2 CR E or N, where A 1 , A 2 One of them is N and the other is CR C or CR E It is.) R A , R B , R C , R D and R E are each independently a hydrogen atom, a halogen atom, or C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 3 ~C 6 Cycloalkyl, substituted by U (C 3 ~C 6 ) Cycloalkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6Alkylthio, halo(C 1 ~C 6 ) Alkylthio, C 1 ~C 6 Alkyl sulfinyl, halo(C 1 ~C 6 ) alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylsulfonyl, -NY 3 Y 4 , cyano, nitro or V; V represents a structure represented by V-1, V-2, V-3, V-4, V-5 or V-6; [ka] Z is independently a hydrogen atom, a halogen atom, or C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkoxy, halo(C 1 ~C 6 ) Alkoxy, C 1 ~C 6 Alkylthio, halo(C 1 ~C 6 ) Alkylthio, C 1 ~C 6 Alkyl sulfinyl, halo(C 1 ~C 6 ) alkylsulfinyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylsulfonyl, -NY 5 Y 6 , cyano or nitro; Q2, Q3 or Q4 represents the number of substituents of Z; Q2 represents an integer of 0, 1 or 2; Q3 represents an integer of 0, 1, 2 or 3; Q4 represents an integer of 0, 1, 2, 3 or 4; When Q2, Q3 or Q4 represents an integer of 2 or more, multiple Z's may be the same or different from each other; Y 3 , Y 4 , Y 5 , Y 6 are each independently a hydrogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkylcarbonyl, halo(C 1 ~C 6 ) Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, halo(C 1 ~C 6 ) alkoxycarbonyl, C 1 ~C 6 Alkyl sulfonyl or halo(C 1 ~C 6 ) alkylsulfonyl; When there are two or more U's, each independently represents cyano, -C(O)OH, or -C(O)NH 2 represents D is a hydrogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkylcarbonyl, halo(C 1 ~C 6 ) Alkylcarbonyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylsulfonyl; E is a hydrogen atom, C 1 ~C 6 Alkyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkylcarbonyl, halo(C 1 ~C 6 ) Alkylcarbonyl, C 1 ~C 6Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylsulfonyl. <3> A 1 is N and A 2 CR E Represented by the formula (1): <1> or a salt thereof, or an N-oxide thereof. <4> A 1 CR C And A 2 is expressed by the formula (1) where N <1> or a salt thereof, or an N-oxide thereof. <5> G 1 G 1 -1, and A 1 is N and A 2 CR E Represented by the formula (1): <1> or a salt thereof, or an N-oxide thereof. <6> G 1 G 1 -1, and A 1 CR C And A 2 is expressed by the formula (1) where N <1> or a salt thereof, or an N-oxide thereof. <7> A 1 is N and A 2 CR E This is expressed by the formula (2). <1> or a salt thereof, or an N-oxide thereof. <8> A 1 CR C And A 2 is expressed by the formula (2) where N <1> or a salt thereof, or an N-oxide thereof. <9> G 2 G 2 -1, and A 1 is N and A 2 CR EThis is expressed by the formula (2). <1> or a salt thereof, or an N-oxide thereof. <10> G 2 G 2 -1, and A 1 CR C And A 2 is expressed by the formula (2) where N <1> or a salt thereof, or an N-oxide thereof. <11> G 2 G 2 -1, and A 1 CR C And A 2 is N and R A C 1 ~C 3 alkylsulfonyl, R B , R D is a hydrogen atom, and R C is a phenyl group optionally substituted with up to five Z's or V; <1> or a salt thereof, or an N-oxide thereof. <12> 2-(3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 180), 2-(3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 181), 2-(3-(ethylsulfonyl)-5-(2-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 174), 2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 175), 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 176), 2-(5-(2,4-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine, 2-(5-(3,5-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 178), 2-(3-(ethylsulfonyl)-5-(2-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine, 2-(3-(ethylsulfonyl)-5-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 214), 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 177) <13> A 1 is N and A 2 CR E This is expressed by the formula (3). <1> or a salt thereof, or an N-oxide thereof. <14> A 1 CR C And A 2 is expressed by the formula (3) where N <1> or a salt thereof, or an N-oxide thereof. <15> G 2 G 2 -1, and A 1 is N and A 2 CR EThis is expressed by the formula (3). <1> or a salt thereof, or an N-oxide thereof. <16> G 2 G 2 -1, and A 1 CR C And A 2 is expressed by the formula (3) where N <1> or a salt thereof, or an N-oxide thereof. <17> <1> ~ <16> or a salt thereof, or an N-oxide thereof, and at least one component selected from the group consisting of a surfactant, a solid carrier, and a liquid carrier. <18> further comprising at least one other pest control compound or agent; <17> The pest control composition according to claim 1. <19> The at least one pest control compound or agent is Aranicalb, Aldicarb, Bendicarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Phenobucarb, Formetanate, Flucythrinate, Isoprocarb, Methiocarb, Methomyl, Oxamyl, Pyrimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, Xylylcarb, Metolcarb, Phenothiocarb, Phenoxycarb, Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Ethylthiometon, Chlorethoxyfos, Kazusaphos, Chloretoxyfos, Chlorfenvinphos, Chloromephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanofenphos, Demeton-S-methyl, Diazinon, Dichlorvos, Dichlorothophos, Dimethoate, Dimethylvinphos, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Phosphamidon, Heptenophos, Imicyafos, Isofenphos, Isopropyl=O-(Methoxyaminothiophosphorylsalicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, PAP, Phorate, Phosalone, Phosphomethan, Phosphamidon, Hoxim, Pyrimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Trichlorfon, Bamidothion, Chlorpyrifos-ethyl, Disulfoton, Sulprofos, Flupyrazofos, Phenthoate, Honphos, Tribufos, Endosulfan, Alpha-endosulfan, Gamma-HCH, Dicofol, Chlordane, Dieldrin, Methoxychlor, Aceprol, Fipronil, Ethiprole, Pyrafluprole, Pyriprole, Flufiprole, Broflanilide, Afoxolaner, Fluralaner, Sarolaner, Fluxametamide, Lotilaner, Isocycloseram, Acrinathrin, Allethrin, d-cis-trans Allethrin, d-trans Allethrin, Bifenthrin,Kappa-bifenthrin, Bioallethrin S-cyclopentenyl, Bioresmethrin, Cycloprothrin, Cyfluthrin, Beta-cyfluthrin, Cyhalothrin, Lambda-cyhalothrin, Gamma-cyhalothrin, Cypermethrin, Alpha-cypermethrin, Beta-cypermethrin, Theta-cypermethrin, Zeta-cypermethrin, Cyphenothrin, Deltamethrin, Empenthrin, Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, Tau-fluvalinate, Halfenp Lox, imiprothrin, cadethrin, permethrin, fenothrin, prallethrin, pyrethrins, resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, phthalthrin, tetramethrin, tralomethrin, transfluthrin, methoxadiazone, metofluthrin, profluthrin, pyrethrum, terallethrin, monfluorothrin, heptafluthrin, meperfluthrin, tetramethylfluthrin, dimefluthrin, chloroparathrin, epsilon-metofluthrin, epsilon-monfluosrin, protrifenbut, acetofluthrin, Tamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, sulfoxaflor, flupyradifurone, triflumezopyrim, dichloromezothiaz, flupirimine, spinosad, spinetoram, abamectin, ivermectin, emamectin benzoate, milbemectin, lepimectin, hydroprene, kinoprene, diofenolan, methoprene, pyriproxyfen, pymetrozine, flonicamid, etoxazole, diafenthiuron, azocyclotine, cyhexatin, fenbutatin oxide, propane Lugit, tetradifon, chlorfenapyr, tralopyril, DNOC, bensultap, cartap, thiocyclam, thiosultap, thiosultap-sodium, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, bistrifluron, buprofezin, cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, amitraz, hydramethylnon, acequinocyl,Fluacrypyrim, pyriminostrobin, flufenoxystrobin, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, piflubumid, metaflumizone, spirodiclofen, spirotetramat, spiromesifen, spiropidione, cyflumetofen, cyenopyrafen, flubendiamide, chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, cyhalodiamide, tetrachlorantraniliprole, quinomethionate, hexythiazox, bifenazate, flufenerim, pyrifluquinazone, flometoquin, fluopyram, fluazaindolizine, amidoflumet, cyclopyrazoflor, thioxazafen, oxazosulfil, Nicotine, chloropicrin, sulfuryl fluoride, crilothier, clofentezine, diflovidazin, rotenone, indoxacarb, piperonyl butoxide, chlordimeform, pyridalyl, azadirachtin, benzoximate, afidopiropen, fluhexafon, fluensulfone, benclothiaz, carsol, insecticidal soap, dimehypo, nithiazine, borate, metaldehyde, ryanodine, sulfuramide, acinonapyr, benzpyrimoxane, 3-bromo-N-(2,4-dichloro-6-(methylcarbamoyl)phenylyl)-1-(3,5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxamide, Metalaxyl, metalaxyl-M, oxadixyl, ofurase, benalaxyl, benalaxyl-M, chiralaxyl, ofurase, furalaxyl, ciprofuran, buprimate, dimethirimol, ethirimol, hymexazole, hydroxyisoxazole, oxathiapiproline, octhilinone, oxolinic acid, benomyl, thiophanate methyl, carbendazim, fuberidazole, thiabendazole, debacarb, diethofencarb, zoxamide, ethaboxam, pencycuron, fluopicolide, fluopimomide, diflumetrim, bupirimate , benodanil, flutolanil, mepronil, isofetamide, fenfuram, oxycarboxin, carboxin, thifluzamide, fluxapyroxad, furametpyr, penflufen, penthiopyrad, benzovindiflupyr, bixafen, isopyrazam, sedaxane, inpirfluxam, fluindapyr, isoflucipram, pyrapropoin, boscalid, azoxystrobin, koumethoxystrobin, kresoxim-methyl, trifloxystrobin, picoxystrobin, pyraclostrobin, dimoxystrobin, metominostrobin, o Lisastrobin, Fluoxastrobin, Pyraoxystrobin, Pyramethostrobin, Flufenoxystrobin, Phenaminestrobin, Enoxastrobin, Cumoxystrobin, Mandestrobin, Triclopyricarb, Famoxadone, Fenamidone, Triclopyricarb, Pyribencarb, Cyazofamid, Amisulbrom, Binapacryl, Meptyldinocarb, Dinocap, Fluazinam, Ferimzone, Fentin Acetate, Fentin Chloride, Fentin Hydroxide, Triphenyltin Hydroxide, Triphenyltin Acetate, Oxine Copper, Silthio FAM, amethoctrazine, mepanipyrim, nitrapyrin, pyrimethanil, cyprodinil, blasticidin S, kasugamycin, kasugamycin hydrochloride hydrate, streptomycin, oxytetracycline, quinoxyfen, proquinazide, fludioxonil, fenpiclonil, fluoroimide, procymidone, iprodione, vinclozolin, edifenphos, iprobenfos, pyrazophos, isoprothiolane, propamocarb, propamocarb hydrochloride, gosei cajeput extract, triforine, pyrifenox, pyrisoxazole, fenarimol,Nuarimol, Azaconazole, Bromuconazole, Diniconazole, Diniconazole-M, Epoxiconazole, Fluquinconazole, Oxpoconazole, Pefurazoate, Difenoconazole, Fenbuconazole, Imibenconazole, Ipconazole, Metconazole, Tetraconazole, Triadimefon, Triadimenol, Triticonazole, Uniconazole, Imazalil, Bitertanol, Triflumizole, Etaconazole, Propiconazole, Penconazole, Flusilazole, Flutriafol, Myclobutanil, Paclobutrazol , prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, ipfentrifluconazole, aldimorph, dodemorph, dodemorph acetate, tridemorph, fenpropimorph, dimethomorph, flumorph, pyrimorph, piperalin, fenpropidin, spiroxamine, fenhexamid, fenpyrazamine, ferbam, metam, methasulfocarb, metiram, thiram, mancozeb, maneb, zineb, ziram, polycarbamate, probineb, thiuram, pyributicarb, validamycin, mil Geomycin, Polyoxin, Benthiavalicarb, Benthiavalicarb Isopropyl, Valifenalate, Iprovalicarb, Mandipropamid, Fenpicoxamide, Florylpicoxamide, Futhalide, Pyroquilon, Tricyclazole, Carpropamid, Diclocymet, Fenoxanil, Acibenzolar-S-methyl, Probenazole, Diclobenthiazox, Tiadinil, Isotianil, Cymoxanil, Fosetyl, Tecloftalam, Triazoxide, Flusulfamide, Diclomedine, Cyflufenamid, Metrafenone, Pyriophenone, Flu Tianil, tebufloquine, ipflufenoquine, fosetylaluminum, tolclofos-methyl, eclumezole, tolprocarb, mefentrifluconazole, quinofumelin, pydiflumetofen, Bordeaux mixture, copper acetate, basic copper sulfate, copper oxychloride, cupric hydroxide, copper oxyquinoline, copper, sulfur, captan, captafol, folpet, anilazine, chlorothalonil, dichlorophen, pentachlorophenol and its salts, hexachlorobenzene, quintozene, iminoctadine acetate, iminoctadine albesilate, guanidine, dodine,Dodine free base, guazatine, guazatine acetate, albesilate, dithianon, fluorimide, tolylfluanid, dichlofluanid, dinobuton, dazomet, pyraziflumide, aminopyrifen, methyltetraprole, pyridaclomethyl, Dipimethitron, Picarburazox, Tecnazene, Nitortal-isopropyl, Dicyclomet, Acibenzolar, Prohexadione-calcium, Bronopol, Diphenylamine, Flumetober, Bentoxazine, Biphenyl, Chloroneb, CNA, Iodocarb, Prothiocarb, and Bacillus genus and insecticidal proteins, bactericidal proteins produced therefrom, insecticidal proteins, bactericidal proteins produced by Bt crops, entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi, <18> The pest control composition according to claim 1. <20> The pest is an animal parasitic pest and is administered to an animal or bird. <18> The pest control composition according to claim 1. <21> pests or their environment <1> 13. A method for controlling pests, comprising contacting the pests with the compound according to claim 12, or a salt thereof, or an N-oxide thereof. <22> A method for increasing crop vigor, comprising administering to a crop or to a crop seed. <1> or a salt thereof, or an N-oxide thereof. <23> <1> or a salt thereof, or an N-oxide thereof, in an amount of about 0.0001 to about 50% by weight of the whole seed after treatment. <1> or a salt thereof, or an N-oxide thereof. <24> <1> 1. A method for producing seeds, comprising a step of treating seeds of a crop with a compound according to any one of claims 1 to 9, or a salt thereof, or an N-oxide thereof, After the treatment, the amount of the seeds is about 0.0001 to about 50% by weight of the whole seeds. <1> or a salt thereof, or an N-oxide thereof. Effect of the Invention

[0007] The compounds represented by formula (1), formula (2) or formula (3) according to the present invention, or salts thereof, or N-oxides thereof, exhibit extremely excellent pest control effects and are useful as pest control agents. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] In this specification, the following terms have the following definitions and meanings:

[0009] Furthermore, the compounds encompassed by the present invention may have optically active forms resulting from the presence of one or more asymmetric carbon atoms or sulfur atoms or axial chirality, and the present invention encompasses all optically active forms and racemic forms.

[0010] Furthermore, the compounds encompassed by the present invention may have tautomers depending on the type of substituent, and the present invention encompasses all tautomers or mixtures of tautomers containing any ratio.

[0011] Furthermore, the compounds included in the present invention may have geometric isomers due to the imino group, and the present invention includes all geometric isomers or a mixture of geometric isomers containing them in any ratio.

[0012] The geometric isomer resulting from the imino group indicates, for example, a bond represented by a wavy line between D in formula (1) and the nitrogen atom of the imino group, and is an isomer mixture containing E isomer, Z isomer, or E isomer and Z isomer in any ratio.

[0013] Among the compounds encompassed by the present invention, those which can be converted into salts by a conventional method include, for example, salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid; salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, and perchloric acid; salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid; salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, and citric acid; salts of amino acids such as glutamic acid and aspartic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium, barium, and magnesium; aluminum salts; and quaternary ammonium salts such as tetramethylammonium salts, tetrabutylammonium salts, and benzyltrimethylammonium salts.

[0014] In the compound of the present invention, the N-oxide is a compound in which a nitrogen atom constituting a ring on a heterocycle is oxidized. Examples of the heterocycle capable of forming an N-oxide include a condensed ring containing a pyridine ring.

[0015] Next, specific examples of the substituents shown in the present specification are shown below, where n- means normal, i- means iso, s- means secondary, tert- means tertiary, and c- means cyclo.

[0016] In the present specification, the term "halogen atom" includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In addition, the term "halo" in the present specification also represents these halogen atoms.

[0017] In this specification, "C a ~C bThe term "alkyl" refers to a linear or branched hydrocarbon group having a to b carbon atoms, and specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a tert-butyl group, an n-pentyl group, a 1,1-dimethylpropyl group, and an n-hexyl group, each of which is selected within the range of the number of carbon atoms specified.

[0018] As used herein, "halo(C a ~C bThe term "alkyl" refers to a linear or branched hydrocarbon group having a to b carbon atoms in which hydrogen atoms bonded to the carbon atoms are substituted with any number of halogen atoms, and in this case, when substituted with two or more halogen atoms, those halogen atoms may be the same or different. For example, a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a trichloromethyl group, a bromodifluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2-chloro-2,2-difluoroethyl group, a 2,2,2-trichloroethyl group, a 2-bromo-2,2-difluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 2-chloro-1,1,2-trifluoroethyl group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2 Specific examples include a 3,3,3-difluoropropyl group, a 3-bromo-3,3-difluoropropyl group, a 2,2,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,1,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group, a 2,2,2-trifluoro-1-(methyl)ethyl group, a 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl group, a 2,2,3,4,4,4-hexafluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, and a nonafluorobutyl group, each of which is selected within the range of the number of carbon atoms specified.

[0019] "C a ~C bThe term "cycloalkyl" refers to a cyclic hydrocarbon group having a to b carbon atoms, which can form a single ring or a compound ring structure having 3 to 6 members. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples include a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a 2,2-dimethylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group, each of which is selected within the range of the specified number of carbon atoms.

[0020] "C a ~C b The term "alkoxy" represents an alkyl-O- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include a methoxy group, an ethoxy group, an n-propyloxy group, an i-propyloxy group, an n-butyloxy group, an i-butyloxy group, an s-butyloxy group, a tert-butyloxy group, and a 2-ethylhexyloxy group, each of which is selected within the range of the number of carbon atoms specified.

[0021] "Haro (C a ~C b The notation of "alkoxy" represents a haloalkyl-O- group having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group, a 2-chloro-1,1,2-trifluoroethoxy group, and a 1,1,2,3,3,3-hexafluoropropyloxy group, each of which is selected within the range of the specified number of carbon atoms.

[0022] "C a ~C bThe term "alkylthio" represents an alkyl-S- group having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, and a tert-butylthio group, each of which is selected within the range of the number of carbon atoms specified.

[0023] As used herein, "halo(C a ~C b The notation of "(trifluoromethyl)thio)" represents a haloalkyl-S- group having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include a difluoromethylthio group, a trifluoromethylthio group, a chlorodifluoromethylthio group, a bromodifluoromethylthio group, a 2,2,2-trifluoroethylthio group, a 1,1,2,2-tetrafluoroethylthio group, a 2-chloro-1,1,2-trifluoroethylthio group, a pentafluoroethylthio group, a 1,1,2,3,3,3-hexafluoropropylthio group, a heptafluoropropylthio group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylthio group, and a nonafluorobutylthio group, and each is selected within the range of the specified number of carbon atoms.

[0024] "C a ~C b The notation of "alkylsulfinyl" represents an alkyl-S(O)- group having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include a methylsulfinyl group, an ethylsulfinyl group, an n-propylsulfinyl group, an i-propylsulfinyl group, an n-butylsulfinyl group, an i-butylsulfinyl group, an s-butylsulfinyl group, and a tert-butylsulfinyl group, each of which is selected within the specified range of the number of carbon atoms.

[0025] As used herein, "halo(C a ~C bThe notation of "(1-(trifluoromethyl)ethylsulfinyl)" represents a haloalkyl-S(O)- group having a to b carbon atoms as defined above. Specific examples thereof include a difluoromethylsulfinyl group, a trifluoromethylsulfinyl group, a chlorodifluoromethylsulfinyl group, a bromodifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylsulfinyl group, and a nonafluorobutylsulfinyl group, each of which is selected within the specified range of carbon atoms.

[0026] "C a ~C b The expression "alkylsulfonyl" means an alkyl-SO 3 having the above-mentioned meaning and containing a to b carbon atoms. 2 - group, and specific examples thereof include a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an i-propylsulfonyl group, an n-butylsulfonyl group, an i-butylsulfonyl group, an s-butylsulfonyl group, and a tert-butylsulfonyl group, each of which is selected within the range of the number of carbon atoms specified.

[0027] As used herein, "halo(C a ~C b The expression "alkylsulfonyl" refers to haloalkyl-SO having the above-mentioned meaning and containing a to b carbon atoms. 2 - group, and specific examples thereof include a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, a chlorodifluoromethylsulfonyl group, a bromodifluoromethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group, a 1,1,2,2-tetrafluoroethylsulfonyl group, and a 2-chloro-1,1,2-trifluoroethylsulfonyl group, and each of these is selected within the range of the number of carbon atoms specified.

[0028] "C a ~C bThe term "alkylcarbonyl" represents the above-mentioned alkyl-C(O)- group having a to b carbon atoms, and specific examples thereof include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a 2-methylbutanoyl group, a pivaloyl group, a hexanoyl group, and a heptanoyl group, each of which is selected within the range of the number of carbon atoms specified.

[0029] "Haro (C a ~C b The notation of "alkylcarbonyl" represents a haloalkyl-C(O)- group having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include a fluoroacetyl group, a chloroacetyl group, a difluoroacetyl group, a dichloroacetyl group, a trifluoroacetyl group, a chlorodifluoroacetyl group, a bromodifluoroacetyl group, a trichloroacetyl group, a pentafluoropropionyl group, a heptafluorobutanoyl group, and a 3-chloro-2,2-dimethylpropanoyl group, and the like, each of which is selected within the specified range of the number of carbon atoms.

[0030] "C a ~C b The term "alkoxycarbonyl" represents the above-mentioned alkyl-OC(O)- group having a to b carbon atoms, and specific examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propyloxycarbonyl group, an i-propyloxycarbonyl group, an n-butoxycarbonyl group, an i-butoxycarbonyl group, an s-butoxycarbonyl group, a tert-butoxycarbonyl group, and a 2-ethylhexyloxycarbonyl group, each of which is selected within the range of the specified number of carbon atoms.

[0031] "Haro (C a ~C bThe notation of "alkoxycarbonyl" represents the above-mentioned haloalkyl-OC(O)- group having a to b carbon atoms, and specific examples thereof include a chloromethoxycarbonyl group, a 2-chloroethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, and a 2,2,2-trichloroethoxycarbonyl group, and the like, each of which is selected within the range of the specified number of carbon atoms.

[0032] "U replaced by (C a ~C b The expression "cycloalkyl" refers to a cycloalkyl group having the above-mentioned meaning, in which the hydrogen atoms bonded to the carbon atoms are replaced by any number of U, and which has a to b carbon atoms, and is selected within the range of the number of carbon atoms specified for each group. a ~C b When there are two or more substituents U on the cycloalkyl group, each U may be the same or different.

[0033] In the compound represented by formula (1) of the present invention, a salt thereof, or an N-oxide thereof, preferably, G 1 is G 1 -1, R 1 , R 2 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, or a halo(C 1 ~C 6 ) alkyl, halo(C 1 ~C 6 ) Alkylthio, Halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) alkylsulfonyl, R A is C 1 ~C 3 Alkoxy, halo(C 1 ~C 3 ) Alkoxy, C 1 ~C 3 Alkylthio, halo(C 1 ~C 3 ) Alkylthio, C1 ~C 3 Alkyl sulfonyl, halo(C 1 ~C 3 ) alkylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, 1 CR C Or N and A 2 CR E or N, where A 1 , A 2 One of them is N and the other is CR C or CR E ), R B , R C , R D and R E are each independently a hydrogen atom, a halogen atom, or C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 alkylsulfonyl, phenyl each independently optionally substituted with up to five Z, V-2, V-4, V-5, V-6, D is a hydrogen atom, C 1 ~C 3 Alkyl, halo(C 1 ~C 3 ) Alkyl, C 1 ~C 6 Alkyl carbonyl, C 3 ~C 6 Cycloalkylcarbonyl, halo(C 1 ~C 6 ) Alkylcarbonyl, C 1 ~C 3 Alkyl sulfonyl, halo(C 1 ~C 3 ) Alkyl sulfonyl, C 1 ~C 3 Alkyloxycarbonyl, halo(C 1 ~C 3 ) alkyloxycarbonyl, benzenecarbonyl each independently optionally substituted with up to 5 T, where T is a hydrogen atom, a halogen atom, C 1 ~C3 Alkyl, halo(C 1 ~C 3 ) Alkyl, C 1 ~C 3 Alkoxy, halo(C 1 ~C 3 ) alkoxy, E is a hydrogen atom, C 1 ~C 6 Alkyl, cyclopropylmethyl, halo(C 1 ~C 6 ) Alkyl, C 1 ~C 6 Alkyl carbonyl, C 3 ~C 6 Cycloalkylcarbonyl, halo(C 1 ~C 6 ) Alkylcarbonyl, C 1 ~C 6 Alkyl sulfonyl, halo(C 1 ~C 6 ) alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl.

[0034] In the compound represented by formula (1) of the present invention, a salt thereof, or an N-oxide thereof, G 1 is G 1 -1, R 1 , R 2 , R 3 and R 4 is a hydrogen atom, halo (C 1 ~C 3 ) alkyl, R A is ethylthio, ethylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, and A is 1 CR C And A 2 is N and R B , R D is a hydrogen atom, and R Care each independently phenyl, 1H-pyrazol-1-yl, or 2H-1,2,3-triazol-2-yl, each of which may be substituted by up to two Z's, Z is hydrogen, fluorine, chlorine, trifluoromethyl, or trifluoromethoxy, D is a hydrogen atom, or acetyl, E is a hydrogen atom, or C 1 ~C 3 Alkyl, cyclopropylmethyl, halo(C 1 ~C 3 ) alkyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl.

[0035] In the compound represented by formula (1) of the present invention, a salt thereof, or an N-oxide thereof, G 1 is G 1 -1, R 1 , R 2 , R 3 and R 4 is a hydrogen atom, halo (C 1 ~C 3 ) alkyl, R A is ethylthio, ethylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, and A is 2 CR E And A 1 is N and R B , R D is a hydrogen atom, and R C are each independently phenyl, 1H-pyrazol-1-yl, or 2H-1,2,3-triazol-2-yl, each of which may be substituted by up to two Z's, Z is hydrogen, fluorine, chlorine, trifluoromethyl, or trifluoromethoxy, D is a hydrogen atom, or acetyl, E is a hydrogen atom, or C 1 ~C 3 Alkyl, cyclopropylmethyl, halo(C 1 ~C 3 ) alkyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl.

[0036] In the compound represented by formula (1) of the present invention, a salt thereof, or an N-oxide thereof, R A is ethylthio, ethylsulfonyl.

[0037] In the compound represented by formula (1) of the present invention, a salt thereof, or an N-oxide thereof is particularly preferably 3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 91), 3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 100), N-((3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)((4-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 101), 3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 103), 3-(ethylsulfonyl)-5-(1H-1,2,4-triazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 105), N-((3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 106), N-((3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 108), 3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)-N-(6-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 109), N-((3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)((6-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 110), N-((3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)-2,2,2-trifluoroacetamide (compound number 111), 3-(ethylsulfonyl)-5-(1H-1,2,3-triazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 120), 5-(Dimethylamino)-3-(ethylsulfonyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 125), 3-(ethylsulfonyl)-5-phenyl-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 127), 5-(4-chloromethyl)-3-(ethylsulfonyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 131), 5-(3,5-dichlorophenyl)-3-(ethylsulfonyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 133), 3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 137), 3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 139), N-((3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 140), 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 142), 5-(2,4-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 144), 5-(3,5-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 146), N-((3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)(methyl(5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 199), 3-(ethylsulfonyl)-5-(3-(trifluoromethoxy)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (compound number 200), N-((3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)(methyl(5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 204), N-((3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)(methyl(5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 205), N-((3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)((methoxymethyl)(5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 207), N-((3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)((methoxymethyl)(5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 209), N-(((ethoxymethyl)(5-(trifluoromethyl)pyridin-2-yl)amino)(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)methylene)acetamide (compound number 211), N-(((cyanomethyl)(5-(trifluoromethyl)pyridin-2-yl)amino)(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)methylene)acetamide (compound number 213), N-((3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 220), N-((ethyl(5-(trifluoromethyl)pyridin-2-yl)amino)(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)methylene)acetamide, N-((3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)(propyl(5-(trifluoromethoxy)pyridin-2-yl)amino)methylene)acetamide, N-(((2-cyanoethyl)(5-(trifluoromethyl)pyridin-2-yl)amino)(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)methylene)acetamide, N-((3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)(((methylsulfonyl)methyl)(5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide, It is.

[0038] In the compound represented by formula (2) of the present invention, a salt thereof, or an N-oxide thereof, preferably, G 2 is G 2 -1, R 1 , R 2 , R 3 and R 4are each independently a hydrogen atom, a halogen atom, or a halo(C 1 ~C 6 ) alkyl, halo(C 1 ~C 6 ) Alkylthio, Halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) alkylsulfonyl, R A is C 1 ~C 3 Alkoxy, halo(C 1 ~C 3 ) Alkoxy, C 1 ~C 3 Alkylthio, halo(C 1 ~C 3 ) Alkylthio, C 1 ~C 3 Alkyl sulfonyl, halo(C 1 ~C 3 ) alkylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, 1 CR C Or N and A 2 CR E or N, where A 1 , A 2 One of them is N and the other is CR C or CR E ), R B , R C , R D and R E are each independently a hydrogen atom, a halogen atom, or C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, , C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 alkylsulfonyl, phenyl each independently optionally substituted with up to five Z's, V-2, V-4, V-5 and V-6.

[0039] In the compound represented by formula (2) of the present invention, a salt thereof, or an N-oxide thereof, G 2 is G 2 -1, R 1 , R 2 , R 3 and R 4 is a hydrogen atom, halo (C 1 ~C 3 ) alkyl, R A is ethylthio, ethylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, and A is 1 CR C And A 2 is N and R B and R D is a hydrogen atom, and R C each independently represents phenyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, or dimethylamino, each of which may be substituted by up to two Z's, and Z represents hydrogen, fluorine, chlorine, trifluoromethyl, or trifluoromethoxy.

[0040] In the compound represented by formula (2) of the present invention, a salt thereof, or an N-oxide thereof, R A is ethylthio, ethylsulfonyl.

[0041] In the compound represented by formula (2) of the present invention, a salt thereof, or an N-oxide thereof, 2-(3-(1H-pyrazol-1-yl)pyridin-4-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 46), 2-(3-(2H-1,2,3-triazol-2yl)pyridin-4-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 48), 2-(3-(2H-1,2,3-triazol-2-yl)pyridin-4-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 170), 5-(Ethylsulfonyl)-N,N-dimethyl-6-(6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)pyridin-3-amine (Compound No. 173), 2-(3-(ethylsulfonyl)-5-(2-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 174), 2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 175), 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 176), 2-(5-(2,4-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine, 2-(3-(ethylsulfonyl)-5-(2-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine, 2-(3-(ethylsulfonyl)-5-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 214), 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 177), 2-(5-(3,5-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 178), 2-(3-(ethylsulfonyl)-5-(pyrimidin-5-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 179), 2-(3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 180), 2-(3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 181) It is.

[0042] The compound represented by formula (2) of the present invention, a salt thereof, or an N-oxide thereof is most preferably 2-(3-(ethylsulfonyl)-5-(2-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 174), 2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 175), 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 176), 2-(5-(2,4-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine, 2-(3-(ethylsulfonyl)-5-(2-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine, 2-(3-(ethylsulfonyl)-5-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 214), 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 177), 2-(5-(3,5-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 178), 2-(3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 180), 2-(3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 181) It is.

[0043] In the compound represented by formula (3) of the present invention, a salt thereof, or an N-oxide thereof, preferably, G 2 is G 2 -1, R 1 , R 2 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, or a halo(C 1 ~C 6 ) alkyl, halo(C 1 ~C 6 ) Alkylthio, Halo(C 1 ~C 6 ) alkylsulfinyl, halo(C 1 ~C 6 ) alkylsulfonyl, R A is C 1 ~C 3 Alkoxy, halo(C 1 ~C3 ) Alkoxy, C 1 ~C 3 Alkylthio, halo(C 1 ~C 3 ) Alkylthio, C 1 ~C 3 Alkyl sulfonyl, halo(C 1 ~C 3 ) alkylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, 1 CR C Or N and A 2 CR E or N, where A 1 , A 2 One of them is N and the other is CR C or CR E ), R B , R C , R D and R E are each independently a hydrogen atom, a halogen atom, or C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 alkylsulfonyl, phenyl each independently optionally substituted with up to five Z's, V-2, V-4, V-5 and V-6.

[0044] In the compound represented by formula (3) of the present invention, a salt thereof, or an N-oxide thereof, G 2 is G 2 -1, R 1 , R 2 , R 3 and R 4 is a hydrogen atom, halo (C 1 ~C 3 ) alkyl, R A is C 1 ~C 3 Alkylthio, C 1 ~C 3 is an alkylsulfonyl; A 1CR C And A 2 is N and R B and R D is a hydrogen atom, and R C each independently represents phenyl, 1H-pyrazol-1-yl, or 2H-1,2,3-triazol-2-yl, each of which may be substituted by up to two Z's, and Z represents hydrogen, fluorine, chlorine, trifluoromethyl, or trifluoromethoxy.

[0045] In the compound represented by formula (3) of the present invention, a salt thereof, or an N-oxide thereof, G 2 is G 2 -1, R 1 , R 2 , R 3 and R 4 is a hydrogen atom, halo (C 1 ~C 3 ) alkyl, R A is C 1 ~C 3 Alkylthio, C 1 ~C 3 is an alkylsulfonyl; A 2 CR E And A 1 is N and R B and R D is a hydrogen atom, and R C each independently represents phenyl, 1H-pyrazol-1-yl, or 2H-1,2,3-triazol-2-yl, each of which may be substituted by up to two Z's, and Z represents hydrogen, fluorine, chlorine, trifluoromethyl, or trifluoromethoxy.

[0046] In the compound represented by formula (3) of the present invention, a salt thereof, or an N-oxide thereof, R A is ethylthio, ethylsulfonyl.

[0047] In the compound represented by formula (3) of the present invention, a salt thereof, or an N-oxide thereof, 2-(3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1,3,5]triazin-4-one (Compound No. 193) 2-(3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1,3,5]triazin-4-one (compound number 215), 2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1,3,5]triazin-4-one (compound number 216), 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1,3,5]triazin-4-one (compound number 217), 2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1,3,5]triazin-4-one (compound number 218), 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxytrifluoromethoxytrifluoromethoxy)phenyl)pyridin-2-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1,3,5]triazin-4-one (compound number 219), It is.

[0048] The compounds represented by formula (1), (2), or (3) of the present invention, or salts thereof, or N-oxides thereof (hereinafter also referred to as compounds of the present invention) can be produced, for example, by the production methods described below, but the present invention is not limited thereto.

[0049] <Manufacturing method 1> [ka] {where, R A, R B , R D , A 1 , A 2 and G 1 indicates that it is the same as the above.}

[0050] Step a By reacting an amine compound represented by formula (4) and a cyano compound represented by formula (5) in the presence of a base and an inert solvent, an amidine compound represented by formula (1-1) can be produced. This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry, 2014, 79(10), p. 4687-4693).

[0051] Examples of the base that can be used in this reaction include alkali metal hydrides such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; normal butyllithium; sodium bis(trimethylsilyl)amide; lithium bis(trimethylsilyl)amide; potassium bis(trimethylsilyl)amide; and lithium diisopropylamine. However, the reactants that can be used in this reaction are not limited to these. The amount of the base used is usually in the range of about 1 to 3 moles per mole of the compound represented by formula (4).

[0052] The inert solvent that can be used in this reaction may be any that does not significantly inhibit this reaction. Examples include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolinone. These inert solvents can be used alone or in a mixture of two or more.

[0053] The reaction temperature in this reaction may be generally in the range of -78°C to the boiling point of the solvent used, and the reaction time may vary depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. The cyano compound represented by formula (5) is generally used in a range of about 1 / 3 to 1 mole or about 1 to 3 moles relative to the amino compound represented by formula (4). This reaction may also be carried out under an atmosphere of an inert gas such as nitrogen gas or argon gas. After the reaction is completed, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product may be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0054] Alternative to step a The amidine compound represented by formula (1-1) can be produced by reacting the amine compound represented by formula (4) with the cyano compound represented by formula (5) in the presence of a Lewis acid. This reaction can be carried out according to the method described in the literature (J. Med. Chem. 2002, 45, 21, 4655-4668).

[0055] Examples of Lewis acids that can be used in this reaction include, but are not limited to, trimethylaluminum, aluminum chloride, titanium tetrachloride, etc. The amount of Lewis acid used is usually in the range of about 1 to 3 times the molar amount of the compound represented by formula (4).

[0056] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction. Examples of the inert solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; and halogenated solvents such as dichloromethane and 1,2-dichloroethane. These inert solvents can be used alone or in combination of two or more.

[0057] The reaction temperature in this reaction may be generally in the range of 0°C to the boiling point of the solvent used, and the reaction time may vary depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. The cyano compound represented by formula (5) is generally used in a range of about 1 to 3 times by mole relative to the amino compound represented by formula (4). This reaction may also be carried out under an atmosphere of an inert gas such as nitrogen gas or argon gas. After the reaction is completed, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0058] Process b [ka] When D is not a hydrogen atom, the amidine compound represented by formula (1-2) can be produced by reacting the amidine compound represented by formula (1-1) with a reactant, optionally in the presence of a base and an inert solvent. {where, R A , R B , R D , A 1 , A 2 , G 1 and D are the same as above.}

[0059] Examples of the reactant that can be used in the present invention include acid chlorides such as acetyl chloride, trifluoroacetyl chloride, methyl chlorocarbonate, methanesulfonic acid chloride, and trifluoromethanesulfonic acid chloride, acid anhydrides such as acetic anhydride, trifluoroacetic anhydride, and trifluorosulfonic acid anhydride, and alkylating agents such as methyl iodide, ethyl iodide, 1,1,1-trifluoro-2-iodoethane, and dimethyl sulfate, but the reactant that can be used in the present reaction is not limited thereto. The amount of the reactant used may be appropriately selected from the range of about 1 to 3 times the molar amount of the compound represented by formula (1-1), and the reactant such as acetic anhydride can be reacted without a solvent by adding an excess amount.

[0060] Examples of the base that can be used in the present invention include triethylamine, N,N-diisopropylethylamine, pyridine, alkali metal hydrides such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride, normal butyllithium, sodium bis(trimethylsilyl)amide, lithium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, and lithium diisopropylamine. The amount of the base used may be appropriately selected usually within a range of about 1 to 5 times the molar amount of the compound represented by formula (8).

[0061] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone, etc. These inert solvents can be used alone or in combination of two or more kinds.

[0062] The reaction temperature in this reaction may be generally in the range of about -78°C to the boiling point of the solvent used, and the reaction time may vary depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. This reaction may also be carried out under an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0063] Process c [ka] When E is not a hydrogen atom, the amidine compound represented by formula (1) can be produced by reacting the amidine compound represented by formula (1-2) with a reactant in the presence of a base and an inert solvent. {where, R A , R B , RD , A 1 , A 2 , G 1 , D and E are the same as above.}

[0064] Examples of the reactant that can be used in the present invention include acid chlorides such as acetyl chloride, trifluoroacetyl chloride, methyl chlorocarbonate, methanesulfonic acid chloride, and trifluoromethanesulfonic acid chloride; acid anhydrides such as acetic anhydride, trifluoroacetic anhydride, and trifluorosulfonic acid anhydride; and alkylating agents such as methyl iodide, ethyl iodide, 1,1,1-trifluoro-2-iodoethane, and dimethyl sulfate, but the reactant that can be used in the present reaction is not limited thereto. The amount of the reactant used may be appropriately selected from the range of about 1 to 3 times the molar amount of the compound represented by formula (1-2).

[0065] Examples of the base that can be used in the present invention include triethylamine, N,N-diisopropylethylamine, pyridine, alkali metal hydrides such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride, normal butyllithium, sodium bis(trimethylsilyl)amide, lithium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, and lithium diisopropylamine. The amount of the base used may be appropriately selected usually within a range of about 1 to 5 times the molar amount of the compound represented by formula (1-2).

[0066] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone, etc. These inert solvents can be used alone or in combination of two or more kinds.

[0067] The reaction temperature in this reaction may be generally in the range of about -78°C to the boiling point of the solvent used, and the reaction time may vary depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. This reaction may also be carried out under an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0068] <Manufacturing method 2> Process d [ka] The amidine compound represented by formula (2) can be produced by reacting the amidine compound represented by formula (1-1) with a reactant in the presence of an inert solvent. This reaction can be carried out according to a method described in the literature (Journal of Organic Chemistry, 2014, 79(10), p. 4687-4693). {where, R A , R B , R D , A 1 , A 2 , G 1 and G 2 indicates the same as above.}

[0069] Examples of the reactant that can be used in the present invention include oxidizing agents such as iodobenzene diacetate, (bis(trifluoroacetoxy)iodo)benzene, iodosylbenzene, (hydroxy(tosyloxy)iodo)benzene, 2-iodoxybenzoic acid, and superatomic iodine compounds such as Dess-Martin periodinane, but the reactants that can be used in the present reaction are not limited thereto. The amount of the reactant used may be appropriately selected from the range of about 1 to 5 times the molar amount of the compound represented by formula (1-1).

[0070] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include halogenated solvents such as dichloromethane and 1,2-dichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene; alcohol solvents such as methanol, ethanol, propanol, 2,2,2-trifluoroethanol and hexafluoro-2-propanol; ethyl acetate; acetonitrile; and the like. These inert solvents can be used alone or in combination of two or more kinds.

[0071] The reaction temperature in this reaction may be generally in the range of about 0°C to the boiling point of the solvent used, and the reaction time may vary depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. This reaction may also be carried out under an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0072] <Manufacturing method 3> Process e [ka] The amidine compound represented by formula (3) can be produced by reacting the amidine compound represented by formula (1-1) with a reactant in the presence of a base and an inert solvent. {where, R A , R B , R D , A 1 , A 2 , G 1 and G 2 indicates the same as above.}

[0073] Examples of the reactant that can be used in the present invention include, but are not limited to, methyl chlorocarbonate, ethyl chlorocarbonate, phenyl chloroformate, 4-nitrophenyl chloroformate, 4-chlorophenyl chloroformate, phosgene, triphosgene, carbonyldiimidazole, etc. The amount of the reactant used may be appropriately selected from the range of usually about 1 to 5 times the molar amount of the compound represented by formula (1-1).

[0074] Examples of the base that can be used in the present invention include triethylamine, N,N-diisopropylethylamine, pyridine, etc., and the amount of the base used may be appropriately selected usually within the range of about 1 to 5 times the molar amount of the compound represented by formula (1-1).

[0075] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include halogenated solvents such as dichloromethane and 1,2-dichloroethane; aromatic hydrocarbons such as benzene, toluene and xylene; chain or cyclic ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene and xylene; polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide and 1,3-dimethyl-2-imidazolinone; ethyl acetate; acetonitrile; and the like. These inert solvents can be used alone or in combination of two or more.

[0076] The reaction temperature in this reaction may be generally in the range of about 0°C to the boiling point of the solvent used, and the reaction time may vary depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. This reaction may also be carried out under an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying it by recrystallization, column chromatography, etc. as necessary.

[0077] Control target The pests to be controlled in the present invention are not particularly limited, and the present invention can be used to control (including killing) a wide range of agricultural and horticultural pests, including mites, nematodes, and soil pests. These pests are defined as agricultural and horticultural pests in the present invention. Preferred examples of insect species to be controlled include the following: Lepidoptera pests {e.g. Chilo suppressalis, Darkheaded stem borer, Chilo polychrysus, White stem borer, Scirpophaga innotata, Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis, Marasmia exigua, Notarcha derogata, Ostrinia furnacalis, European corn borer, Hellula undalis, Herpetogramma luctuosale, Pediasia Crambidae, such as the rice case worm (Nymphula depunctalis), sugarcane borer (Diatraea saccharalis); Pyralidae, such as the corn moth (Elasmopalpus lignosellus) and the Indian meal moth (Plodia interpunctella);Common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), armyworm (Mythimna separata), armyworm moth (Mamestra brassicae), rice cutworm (Sesamia inferens), white armyworm (Spodoptera mauritia), two-banded cutworm moth (Naranga aenescens), leaf fall armyworm (Spodoptera frugiperda), African cutworm (Spodoptera exempta), cutworm moth (Agrotis ipsilon), rice silver looper (Autographa nigrisigna), rice yellow looper (Plusia festucae), soybean looper (Chrysodeixis includens), Trichoplusia spp., false tobacco budworm (Heliothis Heliothis spp. such as Helicoverpa virescens, Helicoverpa spp. such as Helicoverpa armigera and Helicoverpa zea, Noctuidae such as Velvetbean caterpillar (Anticarsia gemmatalis), Cotton leafworm (Alabama argillacea), and Hop vine borer (Hydraecia immanis); Pieridae such as Pieris rapae;Tortricidae, such as the pear fruit moth (Grapholita molesta), the plum fruit moth (Grapholita dimorpha), the bean fruit moth (Leguminivora glycinivorella), the azuki bean leaf moth (Matsumuraeses azukivora), the apple tortrix moth (Adoxophyes orana fasciata), the tea tortrix moth (Homona magnanima), the tea tortrix moth (Archips fuscocupreanus), the codling moth (Cydia pomonella), the tortrix moth (Tetramoera schistaceana), the bean shoot borer (Epinotia aporema), and the citrus fruit borer (Ecdytolopha aurantiana); theivora, Phyllonorycter ringoniella, and other members of the Gracilariidae; Carposinidae, such as Carposina sasakii; Lyonetiidae, such as Leucoptera coffeella, Lyonetia clerkella, and Lyonetia prunifoliella; Lymantriidae, such as Lymantria dispar, and Euproctis pseudoconspersa; Pluteliidae, such as Plutella xylostella;The Gelechiidae include Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, and Tuta absoluta; the Arctiidae include Hyphantria cunea; the Castniidae include Telchin licus; the Cossidae include Cossus insularis; the Geometridae include Ascotis selenaria; the Parasa Limacodidae (Limacodidae) such as Stathmopoda masinissa; Sphingidae (Sphingidae) such as Acherontia lachesis; Sesiidae (Sesiidae) such as Nokona feralis; Hesperiidae (Hesperiidae) such as Parnara guttata. Hemiptera (e.g., Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodes orizicolus, and other Delphacidae pests; Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Empoasca onukii, Empoasca fabae, Dalbulus maidis, Cofana spectra, etc.; Cercopidae, Mahanarva posticata, Mahanarva fimbriolata, etc.;Bean aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), willow aphid (Aphis spiraecola), peach aphid (Myzus persicae), wheat straw aphid (Brachycaudus helichrysi), radish aphid (Brevicoryne brassicae), rosy apple aphid (Dysaphis plantaginea), false radish aphid (Lipaphis erysimi), tulip aphid (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), wheat curl aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus black aphid (Toxoptera citricida), peach butterbur aphid (Hyalopterus pruni), barnyard millet aphid (Melanaphis sacchari), Japanese black aphid (Tetraneura nigriabdominalis), citrus cotton aphid (Ceratovacuna lanigera), apple cotton aphid (Eriosoma lanigerum), and other aphids (Aphididae); grape aphid (Daktulosphaira vitifoliae), pecan phylloxera (Phylloxera devastatrix), pecan leaf phylloxera (Phylloxera notabilis), southern pecan leaf phylloxera (Phylloxera Phylloxeridae, such as Adelges tsugae, Adelges piceae, Aphrastasia pectinatae, etc.; Adelgidae, such as Adelges tsugae, Adelges piceae, Aphrastasia pectinatae, etc.;Rice black bug (Scotinophara lurida), Malayan rice black bug (Scotinophara coarctata), green stink bug (Nezara antennata), spiny spotted bug (Eysarcoris aeneus), large spiny spotted bug (Eysarcoris lewisi), white spotted bug (Eysarcoris ventralis), purple spotted bug (Eysarcoris annamita), brown stink bug (Halyomorpha halys), southern green stink bug (Nezara viridula), brown stink bug (Euschistus heros), red banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelops Pentatomidae such as Scaptocoris melacanthus; Cydnidae such as Scaptocoris castanea (Burrower brown bug); Alydidae such as Riptortus pedestris, Leptocorisa chinensis, and Leptocorisa acuta; Coreidae such as Cletus punctiger and Leptoglossus australis; Caverelius saccharivorus, Togo hemipterus, and Blissus leucopterus; Miridae, including Trigonotylus caelestialium, Stenotus rubrovittatus, Stenodema calcarata, and Lygus lineolaris;Whiteflies of the Aleyrodidae family, such as Trialeurodes vaporariorum, Bemisia tabaci, Dialeurodes citri, Aleurocanthus spiniferus, Aleurocanthus camelliae, and Pealius euryae; scale insects such as Abgrallaspis cyanophylli, Aonidiella aurantii, Diaspidiotus perniciosus, Pseudaulacaspis pentagona, and Unaspis yanonensis; Diaspididae, such as Unaspis yanonensis and Unaspis citri; Coccidae, such as Ceroplastes rubens; Margarodidae, such as Icerya purchasi and Icerya seychellarum; Phenacoccus solani, Phenacoccus solenopsis, Planococcus kraunhiae, Pseudococcus comstocki, Planococcus citri, Pseudococcus calceolariae, long-legged mealybug (Pseudococcus longispinus), and tutle mealybug (Brevennia rehi);Psyllidae family such as Diaphorina citri, Trioza erytreae, Cacopsylla pyrisuga, Cacopsylla chinensis, Bactericera cockerelli, and Cacopsylla pyricola; Corythucha ciliata, Corythucha marmorata, Stephanitis nashi, and Stephanitis pyrioides; Cimicidae family such as Cimex lectularius and Giant Cicada (Quesada gigas) and other cicadas (Cicadidae). Coleoptera (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), Cucurbit beetle (Diabrotica speciosa), Bean leaf beetle (Cerotoma trifurcata), Red-necked leaf beetle (Oulema melanopus), Cucumber leaf beetle (Aulacophora femoralis), Striped flea beetle (Phyllotreta striolata), Cabbage flea beetle (Phyllotreta cruciferae), Western black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado beetle (Leptinotarsa ​​decemlineata), rice leaf beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn flare beetle (Chaetocnema pulicaria), sweet potato spur beetle (Chaetocnema confinis), potato flare beetle (Epitrix cucumeris), rice spur beetle (Dicladispa armigera), southern corn leaf beetle (Myochrous denticollis), four-legged tortoise beetle (Laccoptera quadrimaculata), tobacco flea beetle (Epitrix hirtipennis), etc.; seedcorn beetle (Stenolophus lecontei), slender seedcorn beetle (Clivina Carabidae, such as Carabidae (Impressifrons);Scarabaeidae, such as Anomala cuprea, Anomala rufocuprea, Anomala albopilosa, Popillia japonica, Heptophylla picea, European chafer (Rhizotrogus majalis), black beetle (Tomarus gibbosus), Phyllophaga spp., such as Holotrichia spp. and June beetle (Phyllophaga crinita), Diloboderus spp., such as Diloboderus abderus;Boll weevil (Araecerus coffeae), sweet potato weevil (Cylas formicarius), potato weevil (Euscepes postfasciatus), alfalfa weevil (Hypera postica), maize weevil (Sitophilus zeamais), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), white-spotted weevil (Rhabdoscelus lineatocollis), boll weevil (Anthonomus grandis), grass banded weevil (Sphenophorus venatus), Southern Corn Billbug (Sphenophorus callosus), Soybean stalk weevil (Sternechus subsignatus), Sugarcane weevil (Sphenophorus levis, Scepticus griseus, Scepticus uniformis, Zabrotes subfasciatus, Tomicus piniperda, Hypothenemus hampei, Aracanthus spp. such as Aracanthus mourei, and Eutinobothrus brasiliensis; the family Curculionidae, including Tribolium castaneum and Tribolium confusum; the family Tenebrionidae, including Epilachna vigintioctopunctata and other ladybird beetles (Coccinellidae); Lyctus brunneus and other long-horned wood beetles (Bostrychidae); Ptinidae;Cerambycidae, such as Anoplophora malasiaca and Migdolus fryanus; Elateridae, such as Melanotus okinawensis, Agriotes fuscicollis, Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., and Aeolus spp.; Staphylinidae, such as Paederus fuscipes. ; Thysanoptera (e.g., Thripidae such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, Echinothrips americanus, etc.); Phlaeothripidae such as Haplothrips aculeatus, etc.). Diptera (e.g., Anthomyiidae, such as Delia platura and Delia antiqua; Ulidiidae, such as Tetanops myopaeformis; Agromyzidae, such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, Chromatomyia horticola; Chloropidae, such as Chlorops oryzae; Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera Tephritidae (Fruit Flies) such as Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, and Ceratitis capitata; Ephydridae (Rice Leafminer) such as Hydrellia griseola, Hydrellia philippina, and Hydrellia sasakii; Drosophila suzukii (Drosophila melanogaster); Phoridae (Phoridae) such as Megaselia spiracularis; Clogmia albipunctata (Phosphodiidae); Bradysia Sciaridae (Sciaridae) such as Mayetiola destructor and Orseolia oryzae (Cecidomyiidae) such as Diopsis macrophthalma;Family Tipulidae, including the common cranefly (Tipula aino), the common cranefly (Tipula oleracea), and the European cranefly (Tipula paludosa). Hymenoptera pests {e.g., Tenthredinidae such as Athalia rosae and Athalia japonica; Formicidae such as Solenopsis spp. and Brown leaf-cutting ant Atta capiguara}. Orthoptera pests {e.g., Locusta migratoria, Dociostaurus maroccanus, Chortoicetes terminifera, Nomadacris septemfasciata, Brown Locust, Locustana pardalina, Tree Locust, Calliptamus italicus, Differential grasshopper, Melanoplus differentialis, Two striped grasshopper, Melanoplus bivittatus, Migratory grasshopper, Melanoplus sanguinipes, Red-Legged grasshopper, Melanoplus femurrubrum, Clearwinged grasshopper, Schistocerca the Acrididae, such as the common grasshopper (Gastrimargus musicus), the spur-throated locust (Austracris guttulosa), the oriental grasshopper (Oxya yezoensis), the long-winged grasshopper (Oxya japonica), and the Taiwan grasshopper (Patanga succincta); the Gryllotalpidae, such as the mole cricket (Gryllotalpa orientalis); the Gryllidae, such as the European house cricket (Acheta domestica) and the field cricket (Teleogryllus emma); and the Tettigoniidae, such as the Mormon cricket (Anabrus simplex). Blattodea (e.g., Blattella germanica and other Blattellidae; Periplaneta fuliginosa, Periplaneta americana, Periplaneta brunnea, Blatta orientalis, Periplaneta japonica, Periplaneta australasiae and other Blattidae; Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, 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, etc. (Termitidae). Acari (e.g., Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligonychus spp., and other Tetranychidae; Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculus spp., and other Tetranychidae; 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, Dermacentor taiwanensis, Dermacentor variabilis, Ixodes ovatus, Ixodes persulcatus, and Ixodes black-legged tick. Ixodidae, such as Amblyomma scapularis, Amblyomma americanum, Boophilus microplus, and Rhipicephalus sanguineus;Acaridae (Acarid mites) such as Tyrophagus putrescentiae and Tyrophagus similis; Pyroglyphidae (Pyroglyphidae) such as Dermatophagoides farinae and Dermatophagoides pteronyssinus; Cheyletidae (Cheyletus eruditus), Cheyletus malaccensis, Cheyletus moorei, and Cheyletiella yasguri; Sarcoptidae (Sarcoptes scabiei) and Otodectes cynotis; Demodex canis, etc.; Listrophoridae; Haplochthoniidae; Macronyssidae, such as Ornithonyssus bacoti and Ornithonyssus sylviarum; Dermanyssidae, such as Dermanyssus gallinae; Trombiculidae, such as Leptotrombidium akamushi. Plant parasitic nematodes (e.g., Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi, Bursaphelenchus xylophilus, and other Aphelenchida nematodes, Globodera pallida, Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, Meloidogyne nematode, Heterodera rostochiensis ... arenaria), Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne mali, Pratylenchus coffeae, Pratylenchus drenatus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus vulnus, Radopholus citrophilus, Radopholus mali similis, etc.}

[0078] The compound of the present invention can also be used to control pests such as sanitary pests, shell-storage pests, clothing pests, house pests, and parasitic insects. In particular, it is effective in controlling harmful invertebrates that are harmful to humans and animals, and these pests are defined as animal parasitic pests in the present invention. The animal parasitic pests to be controlled include those that parasitize the back, armpits, lower abdomen, inner thighs, etc. of a host animal and live by obtaining nutrition sources such as blood and dandruff from animals and birds, and those that fly to the back, buttocks, etc. of a host animal and live by obtaining nutrition sources such as blood and dandruff from animals and birds. Examples of animal parasitic pests include mites, lice, and fleas.

[0079] Host animals against which the control agent of the present invention is effective include humans, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, and ferrets; pet birds (e.g., pigeons, parrots, mynah birds, Java sparrows, parakeets, Bengalese finches, and canaries); cattle, horses, pigs, sheep, and goats; poultry (e.g., ducks, chickens, quails, and geese); and honeybees (e.g., European honeybees, Japanese honeybees).

[0080] That is, the pest control agent of the present invention is effective as an animal parasitic pest control agent targeting the above animals and birds.

[0081] The target mites (Acari) include the following pests: Mites of the order Mesostigmata {e.g., Dermanyssidae, such as Dermanyssus gallinae; mites of the genus Ornithonyssus, such as Ornithonyssus sylviarum, Ornithonyssus bursa, and Ornithonyssus bacoti; mites of the genus Laelaps, such as Laelaps echidninus, Laelaps jettmari, and Tropilaelaps clarae; mites of the genus Varroa spp.), Varroa destructor, Varroa jacobsoni, and Varroa underwoodi. Ticks of the order Metastigmata {e.g., Argas spp., Argas persicus, Argas reflexus, Ornithodoros spp., Ornithodoros moubata, Argasidae ticks; Haemaphysalis spp., Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, Haemaphysalis reatii, Haemaphysalis spp. ... leachi, Haemaphysalis longicornis, Haemaphysalis mageshimaensis, Haemaphysalis yeni, Haemaphysalis campanulata, Haemaphysalis pentalagi, Haemaphysalis flava, Haemaphysalis megaspinosa, Haemaphysalis japonica, Haemaphysalis douglasi, Amblyomma spp. such as Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Amblyomma testudinarium, Ixodes spp.) ticks, Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes ovatus, Ixodes persulcatus, Ixodes nipponensis, Boophilus Rhipicephalus spp. include Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) calceratus, and Rhipicephalus spp. include Rhipicephalus evertsi, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, and Rhipicephalus spp. include Rhipicephalus spp. include Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus sanguineus ... appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zambeziensis, Dermacentor spp.Mites of the family Ixodidae, including Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, and Dermacentor variabilis. Astigmata (Acaridida) (e.g. Psoroptidae spp. including Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes spp. including Chorioptes bovis, Otodectes spp. including Otodectes cynotis; Sarcoptes spp. including Sarcoptes scabiei, Sarcoptes spp. including ... canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae, Sarcoptes equi, Sarcoptes suis, Notoedres spp. (Notoedres cati); Knemidokoptidae (Knemidokoptes spp. (Knemidokoptes mutans)). Prostigmata, Actinedida {e.g. Demodex spp., Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Demodex cati; Trombiculidae, Trombicula spp., Trombicula alfreddugesi, Trombicula akamushi}. Lice (Phthiraptera) include the following pests: louse of the suborder Anoplura {e.g. Haematopinus spp., including the horse louse Haematopinus asini, the cow louse Haematopinus eurysternus, and the pig louse Haematopinus suis; Linognathus spp., including the dog louse Linognathus setosus, the cow louse Linognathus vituli, the cow louse Linognathus ovillus, the cow louse Linognathus oviformis, the cow louse Linognathus pedalis, the goat louse Linognathus stenopsis, Solenopotes spp. (Lys of the family Linognathidae) including the hairy cow lice Solenopotes capillatus. Biting louse of the suborder Amblycera (e.g. Menacanthus spp., such as the chicken biting louse (Menacanthus stramineus), the chicken horn biting louse (Menacanthus cornutus), the pale chicken biting louse (Menacanthus pallidulus), biting louse of the family Menoponidae, including Menopon spp., such as the chicken biting louse (Menopon gallinae)). Biting louse of the Ischnocera suborder {e.g. Columbicola spp. (Columbicola columbae), Cuclotogaster spp. (Cuclotogaster heterographus), Goniodes spp. (Goniodes dissimilis), Goniodes gigas, Goniodes gallinae, Lipeurus spp. (Lipeurus caponis) and other biting louse of the Philopteridae family; Bovicola spp. (Philopteridae) {Trichodectidae family including cattle louse (Bovicola bovis), sheep louse (Bovicola ovis), Bovicola limbata, goat louse (Bovicola caprae), horse louse (Bovicola equi), Trichodectes spp. (Trichodectes canis), and Felicola spp. (Felicola subrostrata). Fleas (Siphonaptera) include the following pests: For example, fleas of the family Tungidae, including the sand flea (Tunga penetrans) of the genus Tunga; the dog flea (Ctenocephalides canis) of the genus Ctenocephalides, the cat flea (Ctenocephalides felis), the hedgehog flea (Archaeopsylla erinacei) of the genus Archaeopsylla, the Asian rat flea (Xenopsylla cheopis) of the genus Xenopsylla, the human flea (Pulex irritans) of the genus Pulex, the chicken lift flea (Echidnophaga spp.) of the genus Echidnophaga. fleas of the family Pulicidae, including the human flea (Ceratophyllus gallinae), the Japanese rat flea (Ceratophyllus anisus), and the European mouse flea (Nosopsyllus fasciatus); fleas of the family Ceratophyllidae, including the European rat flea (Ceratophyllus gallinae), the Japanese rat flea (Ceratophyllus anisus), and the European mouse flea (Nosopsyllus fasciatus); fleas of the family Leptopsyllidae, including the blind rat flea (Leptopsylla segnis). Other target animal parasitic pests include pests of the order Hemiptera, such as insects of the family Cimicidae, including Cimex lectularius, and insects of the family Reduviidae, including Panstrongylus spp., Rhodnius prolixus, and Triatoma infestans. Other pests that are effective against Diptera pests are biting insects (chewing flies, adult blood-sucking flies, migratory Diptera larvae, and parasitic fly maggots). Diptera pests include: Nematocera {e.g. (a) Culex spp., Culex quinquefasciatus, Culex pipiens pallens, Culex tarsalis, Culex pipiens molestus, Culex pipiens fatigans, Culex tritaeniorhynchus summorosus, Armigeres spp., Armigeres subalbatus, Anopheles spp., Anopheles gambiae, Anopheles maculipennis, Anopheles (b) mosquitoes of the family Culicidae, including Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Aedes togoi, and Aedes vexans nipponii; (c) mosquitoes of the family Simulium spp., including Simulium reptans, Simulium ornatum, Simulium venustum, Simulium salopiense, Prosimulium Black flies of the family Simuliidae, including Prosimulium yezoense (Culiodes spp.);) Ceratopogonidae midges, including Culicoides arakawae, Culicoides pictimargo, Culicoides kibunensis, Culicoides homotomus, Culicoides oxystoma, Culicoides nipponensis, Culicoides punctatus, Culicoides maculatus, and Culicoides matsuzawai.} (a) the suborder Brachyceratopsis {e.g., (a) Tabanus spp. such as Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Tabanus trigonus, Tabanus chrysurus, Tabanus trigeminus, Tabanus fulvimedioides, Tabanus iyoensis, and Chrysops spp. such as Chrysops caecutiens, Chrysops relictus, Chrysops Tabanidae including Chrysops suavis and Chrysops japonicus; Muscina spp. including Musca domestica, Musca bezzii, Musca hervei, Musca conducens, Musca stabulans, Stomoxys spp. including Stomoxys calcitrans and Haematobia spp.Flies of the family Muscidae, including Haematobia irritans, Haematobia irritans exigua, Haematobia stimulans, Fannia spp., Fannia canisularis; Flies of the family Glossinidae, including Glossina spp.; Flies of the family Hippoboscidae, including Melophagus spp., Melophagus ovinus; Calliphora spp., Calliphora lata; Lucilia spp. Flies of the family Calliphoridae, including Lucilia (Phaenicia) cuprina, Lucilia (Phaenicia) sericata, Lucilia illustris, Chrysomyia. spp., Chrysomya hominivorax, Chrysomya chloropyga, and Chrysomya bezziana; flies of the subfamily Cuterebrinae, including Cuterebra spp., Hypodermatinae, and Hypoderma spp. bovis, Hypoderma lineatum, Gasterophilinae and even Gasterophilus spp.) bot flies (Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum, and flies of the Oestrinae family (including the Oestrus spp. bot flies, Oestrus ovis).

[0082] When the compound of the present invention is used as an agricultural and horticultural pest control agent, the compound of the present invention may be used as it is, or may be mixed with a suitable solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant, other formulation auxiliary, etc. to prepare an agrochemical formulation. As the agrochemical formulation, preferably, emulsifiable concentrate, EW agent, liquid agent, suspension, wettable powder, granular wettable powder, dust, DL dust, powder granule, granule, tablet, oil agent, aerosol, flowable agent, dry flowable agent, microcapsule agent, etc. can be mentioned. These agrochemical formulations can be used in any formulation type selected. In the present invention, the carrier refers to a solid carrier, liquid carrier, gaseous carrier, etc.

[0083] Examples of the solid carrier include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, acid clay, quartz sand, silica stone, zeolite, perlite, attapulgite, pumice, ammonium sulfate, sodium sulfate, and urea. Examples of the liquid carrier include alcohols such as methanol, ethanol, n-hexanol, ethylene glycol, and propylene glycol; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; aliphatic hydrocarbons such as n-hexane, kerosene, and kerosene; aromatic hydrocarbons such as toluene, xylene, and methylnaphthalene; ethers such as diethyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; nitriles such as acetonitrile and isobutyronitrile; acid amides such as dimethylformamide and dimethylacetamide; vegetable oils such as soybean oil and cottonseed oil; dimethyl sulfoxide; and water. Examples of the gaseous carrier include LPG, air, nitrogen, carbon dioxide, and dimethyl ether. Examples of the surfactant and dispersant include alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, lignin sulfonates, alkyl sulfosuccinates, formalin condensates of alkyl naphthalene sulfonates, polycarboxylates, POE polystyryl phenyl ether sulfates and phosphates, and POE·POP block polymers. Furthermore, examples of the formulation auxiliary include carboxymethyl cellulose, hydroxypropyl cellulose, polyvinyl alcohol, xanthan gum, pregelatinized starch, gum arabic, polyvinylpyrrolidone, ethylene-acrylic acid copolymer, ethylene-vinyl acetate copolymer, polyethylene glycol, liquid paraffin, calcium stearate, antifoaming agents, preservatives, and the like. The above-mentioned various carriers, surfactants, dispersants, and formulation auxiliary agents can be used either alone or in combination, as required.

[0084] The content of the compound of the present invention, which is an active ingredient, in the pesticide formulation is not particularly limited, but is preferably 1 to 75% by weight for emulsifiable concentrates, 0.3 to 25% by weight for dusts, 1 to 90% by weight for wettable powders, and 0.1 to 10% by weight for granules.

[0085] When the compound of the present invention is used as an agent for controlling mites that parasitize livestock such as cows and pigs, and pets such as dogs and cats, the amount used is not particularly limited, but can be, for example, an amount of 0.01 to 1000 mg of the active ingredient per 1 kg of the host animal. The compound of the present invention can be applied to a host animal by a known veterinary method. For example, when the purpose is systemic suppression, the compound can be administered to an animal by tablet, capsule, immersion solution, feeding, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), etc. When the purpose is non-systemic suppression, the compound can be administered by spraying, pouring, or spot-on with an oily or aqueous liquid, or the compound can be kneaded into a resin, and the kneaded product can be molded into a suitable shape such as a collar or ear tag, and the compound can be attached to an animal.

[0086] The pesticide according to the present invention can be used as it is or after dilution. The pesticide according to the present invention can be mixed or used in combination with other insecticides, nematicides, fungicides, acaricides, herbicides, plant growth regulators, fertilizers, etc. Examples of the pesticides that can be mixed or used in combination include those described in the Pesticide Manual (17th edition, published by The British Crop Protection Council), Shibuya Index (SHIBUYA INDEX 17th edition, 2014, published by SHIBUYA INDEX RESEARCH GROUP), and the IRAC Mode of Action Classification Scheme (Mode of Action Classification Scheme Version 8.2 edition, published by IRAC), and the FRAC Code List (FRAC Code List (C) * 2017: Fungicides sorted by mode of action, 2017 edition, published by FRAC), and those whose structures can be identified on the Internet (http: / / www.alanwood.net / pesticides / sitemap.html).

[0087] More specifically, the insecticide may be, for example, alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, ), carbamate compounds such as isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb, metolcarb, fenothiocarb, and fenoxycarb; Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, ethylthiometon, chlorethoxyfos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, EPN, ethion, etoprophos, famphur, fenamifos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos , isofenphos, isopropyl O-(methoxyaminothiophosphoryl)salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton ethyl, parathion, parathion-methyl, PAP, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos , organic phosphate ester compounds such as propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, chlorpyrifos-ethyl, disulfoton, sulprofos, flupyrazophos, phenthoate, fonofos, and tribufos; Organochlorines such as endosulfan, alpha-endosulfan, gamma-HCH, dicofol, chlordane, dieldrin, and methoxychlor; Phenylpyrazole compounds such as acetoprole, fipronil, ethiprole, pyrafluprole, pyriprole, and flufiprole; Metadiamide compounds such as broflanilide, isoxazoline compounds such as afoxolaner, fluralaner, sarolaner, fluxametamide, lotilaner, and isocycloseram; Acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin S-cyclopentenyl S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esphethrin esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin, prallethrin, pyrethrin, resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, phthalthrin,Pyrethroid compounds such as tetramethrin, tralomethrin, transfluthrin, metoxadiazone, metofluthrin, profluthrin, pyrethrum, terallethrin, momfluorothrin, heptafluthrin, meperfluthrin, tetramethylfluthrin, dimefluthrin, chloroprallethrin, ipsilon - metofluthrin, ipsilon - momfluorothrin, protrifenbut, Neonicotinoid compounds such as acetamiprid, chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, Sulfoximine compounds such as sulfoxaflor, Butenolide compounds such as flupyradifurone, Mesoionic compounds such as triflumezopyrim, dicloromezotiaz, 2 - Aminopyridine compounds such as flupyrimin Spinosyn compounds such as spinosad, spinetoram, Macrolides such as abamectin, ivermectin, emamectin benzoate, milbemectin, and lepimectin; Juvenile hormone-like compounds such as hydroprene, quinoprene, diofenolan, and methoprene; 4-phenoxyphenoxy compounds such as pyriproxyfene, Pyridine azomethine compounds such as pymetrozine, pyridinecarboxamide compounds such as flonicamid; Oxazole compounds such as ethoxazole, Bacillus thuringiensis and Bacillus sphaericus agents such as Bt subsp. israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. tenebrionis and the insecticidal proteins they produce; Insecticidal proteins produced by the Bt crops (genetically modified crops that have been engineered to resist pests by incorporating a gene that produces a Bacillus thuringiensis toxin) that fall under the above category, Thiourea compounds such as diafenthiuron, Organometallic compounds such as azocyclotin, cyhexatin, and fenbutatin oxide; Sulfite esters and diphenyl ether compounds such as propargite, Diphenylsulfone compounds such as tetradifon, Pyrrole compounds such as chlorfenapyr and tralopyril, Dinitro compounds such as DNOC, Nereistoxin analogues such as bensultap, cartap, thiocyclam, thiosultap, and thiosultap sodium; Benzoyl urea compounds such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, and bistrifluron; thiadiazine compounds such as buprofezin, Triazole compounds such as cyromazine, diacylhydrazine compounds such as chromafenozide, halofenozide, methoxyfenozide, and tebufenozide; Amidine compounds such as amitraz Amidinohydrazone compounds such as hydramethylnon, Naphthoquinone compounds such as acequinocyl, Strobilurin compounds such as fluacrypyrim, pyriminostrobin, and flufenoxystrobin; quinazoline compounds such as fenazaquin, phenoxypyrazole compounds such as fenpyroxymate; Phenoxyethylamine compounds such as pyrimidifen, Pyridazinone compounds such as pyridaben, pyrazolecarboxamide compounds such as tebufenpyrad, tolfenpyrad, and pyflubumide; hydrazinecarboxamide compounds such as metaflumizone; Tetronic and tetramic acid compounds such as spirodiclofen, spirotetramat, spiromesifen, and spiropidion; beta-ketonitrile compounds such as cyflumetofen and cyenopyrafen; Phthalic acid amide compounds such as flubendiamide, anthranilic acid amide compounds such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, cyhalodiamide, and tetrachlorantraniliprole; quinoxaline compounds such as quinomethionate; thiazolidinone compounds such as hexythiazox, hydrazine compounds such as bifenazate; Pyridinamine compounds such as flufenerim, Aminoquinazoline compounds such as pyrifluquinazon, 6-phenoxyquinoline compounds such as flometoquin, pyridinylethylbenzamide compounds such as fluopyram; Sulfonamide compounds such as fluazaindolizine and amidoflumet Pyridylpyrazole compounds such as tyclopyrazoflor oxadiazole compounds such as tioxazafen; Benzoxazole compounds such as oxazosulfyl It could be. Other insecticides include nicotine, chloropicrin, sulfuryl fluoride, crylotie, clofentezine, diflovidazin, rotenone, indoxacarb, piperonyl butoxide, and nicotine-based insecticides. butoxide, chlordimeform, pyridalyl, azadirachtin, benzoxymate, afidopyropen, fluhexafon, fluensulfone, benclothiaz, carzole, insecticidal soap, dimehypo, nithiazine, borate Examples of compounds include 3-bromo-N-(2,4-dichloro-6-(methylcarbamoyl)phenylyl)-1-(3,5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxamide. Furthermore, the pest control agent according to the present invention can be mixed or used in combination with a microbial pesticide such as an insect pathogenic bacterium, an insect pathogenic virus, or an insect pathogenic fungus.

[0088] The fungicides used include, for example, phenylamide compounds such as metalaxyl, metalaxyl-M, oxadixyl, ofurase, benalaxyl, benalaxyl-M, kiralaxyl, ofurase, furalaxyl, and cyprofuram; Hydroxypyrimidine compounds such as bupyrimate, dimethilimol, and ethilimol; Isoxazole compounds such as hymexazole and hydroxyisoxazole; piperidinyl thiazole isoxazoline compounds such as oxathiapiprolin; isothiazolone compounds such as octhilinone, Carboxylic acid compounds such as oxolinic acid, Benzimidazole-thiophanate compounds such as benomyl, thiophanate-methyl, carbendazim, fuberidazole, thiabendazole, and debacarb; N-phenylcarbamate compounds such as diethofencarb, Toluamide compounds such as zoxamide, Ethylaminothiazolecarboxamide compounds such as ethaboxam; Phenylurea compounds such as pencycuron, pyridinylmethylbenzamide compounds such as fluopicolide and fluopimomide; pyrimidineamine compounds such as diflumetorim and bupirimate; benzanilide compounds such as benodanil, flutolanil, and mepronil; Phenyloxoethylthiophene amide compounds such as isofetamide, pyridinylethylbenzamide compounds such as fluopyram; Furancarboxamide compounds such as fenfuram, Oxathiincarboxamide compounds such as oxycarboxin and carboxin; Thiazolecarboxamide compounds such as thifluzamide, pyrazole-4-carboxamide compounds such as fluxapyroxad, furametpyr, penflufen, penthiopyrad, benzovindiflupyr, bixafen, isopyrazam, sedaxane, inpyrfluxam, fluindapyr, isoflucipram, and pyrapropoyne; pyridinecarboxamide compounds such as boscalid, Strobilurin compounds such as azoxystrobin, coumetoxystrobin, kresoxym-methyl, trifloxystrobin, picoxystrobin, pyraclostrobin, dimoxystrobin, metominostrobin, orysastrobin, fluoxastrobin, pyraoxystrobin, pyrametostrobin, flufenoxystrobin, phenaminestrobin, enoxastrobin, coumoxystrobin, mandestrobin, and triclopyricarb; oxazolidinedione compounds such as famoxadone, Imidazolinone compounds such as fenamidone, benzyl carbamate compounds such as triclopyricarab and pyribencarb; cyanoimidazole compounds such as cyazofamid; Sulfamoyltriazole compounds such as amisulbrom; Dinitrophenyl croton compounds such as binapacryl, meptyldinocarb, and dinocap; 2,6-dinitroaniline compounds such as fluazinam, pyrimidinone hydrazone compounds such as ferimzone, Organic and inorganic metal compounds such as fentin acetate, fentin chloride, fentin hydroxide, triphenyltin hydroxide, triphenyltin acetate, and oxine copper; Thiophenecarboxamide compounds such as silthiofam, triazolopyrimidine amine compounds such as ametoctradin, Anilinopyrimidine compounds such as mepanipyrim, nitrapyrin, pyrimethanil, and cyprodinil; enopyranuronic acid antibiotics such as blasticidin-S; hexopyranosyl antibiotics such as kasugamycin and kasugamycin hydrochloride hydrate; glucopyranosyl antibiotics such as streptomycin, Tetracycline antibiotics such as oxytetracycline, aryloxyquinoline compounds such as quinoxyfen, quinazoline compounds such as proquinazid, cyanopyrrole compounds such as fludioxonil and fenpiclonil; dicarboximide compounds such as fluoroimide, procymidone, iprodione, and vinclozolin; Phosphorothiolate compounds such as edifenphos, iprobenfos, and pyrazophos; Dithiolane compounds such as isoprothiolane, Propylcarbamate compounds such as propamocarb and propamocarb hydrochloride; Bacillus species, such as Bacillus subtilis (strains QST713, FZB24, MBI600, D747) and the bactericidal proteins produced therefrom, and bactericidal proteins produced by said Bt crops; Terpene hydrocarbons and terpene alcohols, such as extracts of Gosei Kayputa, Piperazine compounds such as triforine, Pyridine compounds such as pyrifenox and pyrisoxazole, Pyrimidine compounds such as fenarimol and nuarimol, Azaconazole, bromuconazole, diniconazole, diniconazole-M, epoxyconazole, fluquinconazole, oxpoconazole, pefurazoate, difenoconazole, fenbuconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, imazalil azole compounds such as mazalil, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, flutriafol, myclobutanil, paclobutrazol, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, ipfentrifluconazole, and mefentrifluconazole; Morpholine compounds such as aldimorph, dodemorph, dodemorph acetate, tridemorph, fenpropimorph, dimethomorph, flumorph, and pyrimorph; piperidine compounds such as piperalin and fenpropidin; Spiroketalamine compounds such as spiroxamine, Hydroxyanilides such as fenhexamid, Aminopyrazolinone compounds such as fenpyrazamine, Thiocarbamate and dithiocarbamate compounds such as ferbam, metam, metasulphocarb, metiram, thiram, mancozeb, maneb, zineb, ziram, polycarbamate, propineb, thiuram, and pyributicarb; glucopyranosyl antibiotics such as validamycin, nucleoside antibiotics such as mildiomycin and polyoxin; Valinamide carbamate compounds such as benthiavalicarb, benthiavalicarb-isopropyl, valifenalate, and iprovalicarb; Mandelic acid amide compounds such as mandipropamid, Picolinamide compounds such as fenpicoxamid and florylpicoxamid; isobenzofuranone compounds such as fthalide, Pyrroloquinolinone compounds such as pyroquilone, triazolobenzothiazole compounds such as tricyclazole; Cyclopropanecarboxamide compounds such as carpropamid; Carboxamide compounds such as diclocymet, Propionamide compounds such as fenoxanil, Benzothiadiazole compounds such as acibenzolar-S-methyl, Benzisothiazole compounds such as probenazole and dichlobentiazox, Thiadiazole carboxamide compounds such as tiadinil, isothiazolecarboxamide compounds such as isotianil; Cyanoacetamide oxime compounds such as cymoxanil, Ethyl phosphonates such as fosetyl, Phthalamic acid compounds such as techlophthalam, Benzotriazine compounds such as triazoxide, benzenesulfonic acid compounds such as flusulfamide, Pyridazinone compounds such as diclomezine, Phenylacetamide compounds such as cyflufenamide, Benzophenone compounds such as metrafenopne, Benzoyl pyridine compounds such as pyriofenone, Cyano methylene thiazolidine compounds such as flutianil, 4 - Quinolyl acetic acid compounds such as tebufloquin, 3 - Phenoxyquinoline compounds such as ipflufenoquin, Organophosphorus compounds such as fosetyl - aluminium and tolclofos - methyl, 1,2,4 - Thiadiazole compounds such as echlomezole, Trifluoroethyl carbamate compounds such as tolprocarb, Pyrazole carboxamide compounds such as pydiflumetofen, Copper - based compounds such as Bordeaux mixture, copper acetate, basic copper sulfate, oxy copper chloride, copper hydroxide, and oxine - copper, Inorganic compounds such as copper and sulfur, N - halogenothioalkyl compounds such as captan, captafol, and folpet, Organochlorine compounds such as anilazine, chlorothalonil, dichlorophen, pentachlorophenol and its salts, hexachlorobenzene, and quintozene, guanidine compounds such as iminoctadine triacetate salt, iminoctadine albesilate, guanidine, dodine, dodine free base, guazatine, guazatine acetate salt, and albesilate; anthraquinone compounds such as dithianon, quinoxaline compounds such as quinomethionate; Maleimide compounds such as fluoroimide; Sulfenic acid compounds such as tolylfluanid and dichlofluanid; dinitrophenolic compounds such as dinobuton, Cyclic dithiocarbamate compounds such as dazomet Anilides such as pyraziflumid, Nicotinic acid ester compounds such as aminopyrifen, Tetrazolinone compounds such as methyltetraprole, Pyridazine compounds such as pyridachlometyl is possible. Other fungicides include quinofumelin, dipymetitrone, picarbutrazox, tecnazen, nitrthal-isopropyl, dicyclomet, acibenzolar, prohexadione-calcium, bronopol, diphenylamine, flumetover, bethoxazin, biphenyl, chloroneb, CNA, iodocarb, and prothiocarb.

[0089] The compound of the present invention or its agriculturally and horticulturally acceptable acid addition salt can be used for controlling the target pest by applying an effective amount to plants or soil. The amount of the active ingredient in the formulation is 0.01 to 90% by weight. The wettable powder, emulsifiable concentrate, suspension concentrate, flowable concentrate, water-soluble concentrate, and water-dispersible granule can be diluted with water to a desired concentration and sprayed on plants or soil in the form of a solution, suspension, or emulsion, while the dust or granule can be sprayed as it is. When the compound of the present invention or its agriculturally and horticulturally acceptable acid addition salt is used for quarantine purposes, the emulsifiable concentrate, wettable powder, flowable concentrate, etc. can be diluted with water to a desired concentration and applied, while the oil solution, aerosol, fog, poison bait, anti-mite sheet, etc. can be used as they are. In this specification, the term "crop" refers to cultivated plants in general, and specifically refers to food crops, forage crops, green manure crops, horticultural crops (including ornamental plants), and industrial crops. The invention also includes a method for enhancing the vigor of a crop, the method comprising contacting the crop or a seed of the crop with a compound of the invention.The invention also includes a method for producing a seed of the crop, the method comprising treating the seed of the crop with a compound of the invention. When the subject of treatment or contact is a seed, the amount of the compound of the present invention or its agriculturally and horticulturally acceptable acid addition salt is not limited, but it is preferable that the compound of the present invention or its agriculturally and horticulturally acceptable acid addition salt is contained in an amount of about 0.0001 to about 50% by weight, in terms of the active ingredient, based on the weight of the seed after treatment. The present invention further provides the use of the compound of the present invention or an acid addition salt thereof as an active ingredient in a composition for protecting animals or birds from animal parasitic pests. The composition contains the compound of the present invention or an acid addition salt thereof in an amount that is parasiticidally effective and does not harm the target animal or bird. The compound of the present invention or an acid addition salt thereof is contacted with the pest or its environment, such as animals or birds, crops, crop seeds, soil, etc., in a biologically effective amount to control the invertebrate pest.

[0090] Next, specific examples of the compound of the present invention are shown below. [ka]

[0091] G in Equation (1) 1 G 1 In formula (1-3), R 1 , R 2 , R 3 , R 4 , A 1 , A 2 is a substituent listed in Table 1, D is a substituent listed in Table 2, E is a substituent listed in Table 3, R A is a substituent as described in Table 4, and R B , R D , R E The compound of the present invention in which the substituents are as shown in Table 5.

[0092] [Table 1]

[0093] [Table 2]

[0094] [Table 3]

[0095] [Table 4]

[0096] [Table 5]

[0097] G in Equation (1) 1 G 1 In formula (1-3), R 1 , R 2 , R 3 , R 4 , A 1 , A 2 is a substituent listed in Table 6, D is a substituent listed in Table 2, E is a substituent listed in Table 3, R A is a substituent as described in Table 4, and R B , R C , R D The compound of the present invention in which the combination is a substituent as described in Table 7.

[0098] [Table 6]

[0099] [Table 7-1]

[0100] [Table 7-2]

[0101] G in Equation (2) 2 G 2 In formula (2-1), R 1 , R2 , R 3 , R 4 , A 1 , A 2 is a substituent as described in Table 1, and R A is a substituent as described in Table 4, and R B , R D , R E is a combination of the substituents shown in Table 5. [ka]

[0102] G in Equation (2) 2 G 2 In formula (2-1), R 1 , R 2 , R 3 , R 4 , A 1 , A 2 is a substituent as described in Table 6, and R A is a substituent as described in Table 4, and R B , R C , R D The compound of the present invention in which the combination is a substituent as described in Table 7.

[0103] G in Equation (3) 2 G 2 In formula (3-1), R 1 , R 2 , R 3 , R 4 , A 1 , A 2 is a substituent as described in Table 1, and R A is a substituent as described in Table 4, and R B , R D , R E is a combination of the substituents shown in Table 5. [ka]

[0104] G in Equation (3) 2 G 2 In formula (3-1), R 1, R 2 , R 3 , R 4 , A 1 , A 2 is a substituent as described in Table 6, and R A is a substituent as described in Table 4, and R B , R C , R D The compound of the present invention in which the combination is a substituent as described in Table 7.

[0105] <Synthesis Examples> The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. In the NMR data, "s" indicates singlet, "d" indicates doublet, "t" indicates triplet, "q" indicates quartet, "m" indicates multiplet, "broad" indicates broad line, and J indicates a coupling constant.

[0106] Synthesis Example 1-1-1: Preparation of 3-(1H-pyrazol-1-yl)isonicotinonitrile 3-Chloroisonicotinonitrile (1.00g, 7.22mmol) and 1H-pyrazole (0.52g, 7.94mmol) were dissolved in N,N-dimethylformamide (10ml), cooled in an ice bath, sodium hydride (0.35g, 7.94mmol) was added, and the mixture was stirred at room temperature for 1.5 hours. Water was added, and the mixture was extracted three times with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure using an evaporator. The crude product obtained was purified by silica gel chromatography to obtain the target product (0.79g, 64.2%, white solid). 1H NMR (CDCl 3 ) δ9.17(1H, s), 8.71(1H, s, J=5.1Hz), 8.17(1H, d, J=2.7Hz), 7.88(1H, d, J=1.5Hz), 7.65(1H, dd, J=5.1, 0.6Hz), 6.62(1H, dd, J=2.7, 0.6Hz)

[0107] Synthesis Example 1-1-2: Preparation of 3-(1H-pyrazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)isonicotinimidamide (Compound No. 5) 5-(trifluoromethyl)pyridin-2-amine (0.52 g, 3.23 mmol) was dissolved in N,N-dimethylformamide (15 mL), sodium hydride (content 55%, 0.14 g, 3.23 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. 3-(1H-pyrazol-1-yl)isonicotinonitrile (0.50 g, 2.94 mmol) prepared in Synthesis Example 1-1-1 was added thereto, and the mixture was stirred at the same temperature for one hour, and then sodium hydride (content 55%, 0.05 g, 1.15 mmol) was added, and the mixture was stirred at the same temperature for another 17 hours. Water was added, and the mixture was extracted three times with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the target product (0.57 g, 58.6%, white solid). 1H NMR (CDCl 3 ) δ10.36(1H, broad), 8.90-8.70(2H, m), 8.55(1H, s), 7.95-7.81(2H, m), 7.81-7.70(2H, m), 7.24(1H, d, J=9.0Hz), 6.49(1H, broad), 6.53(1H, t, J=2.1Hz)

[0108] Synthesis Example 1-1-3: Preparation of N-((3-(1H-pyrazol-1-yl)pyridin-4-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (Compound No. 14) Acetic anhydride (6 mL) was added to 3-(1H-pyrazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)isonicotinimidamide (0.30 g, 0.90 mmol) prepared in Synthesis Example 1-1-2, and the mixture was stirred under reflux for 15 minutes. Acetic anhydride was distilled off under reduced pressure at the same temperature, and the resulting crude product was purified by silica gel chromatography to obtain the target product (0.26 g, 76.9%, white viscous material). 1H NMR (CDCl 3) δ12.90(1H, s), 8.77(1H, s), 8.77-8.63(2H, m), 7.99(1H, d, J=7.8Hz), 7.76(1H, d, J=1.8Hz), 7.69(1H, s), 7.53(1H, d, J=4.8Hz), 7.38(1H, d, J=8.4Hz), 6.44(1H, s), 1.96(3H, s)

[0109] Synthesis Example 1-1-4: Preparation of N-((3-(1H-pyrazol-1-yl)pyridin-4-yl)(methyl(5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (Compound No. 17) N-((3-(1H-pyrazol-1-yl)pyridin-4-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (0.13 g, 0.35 mmol) prepared in Synthesis Example 1-1-3 was dissolved in N,N-dimethylformamide (2.6 mL), sodium hydride (content 55%, 0.02 g, 0.41 mmol) was added, and the mixture was stirred at room temperature for 10 minutes. Methyl iodide (25 μL, 0.40 mmol) was added thereto, and the mixture was stirred at the same temperature for 3 hours, after which water was added and the mixture was extracted twice with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the target product (8.8 mg, 6.5%, yellow viscous product). 1H NMR (CDCl 3 ) δ8.70(1H, s), 8.56(1H, s), 8.43(1H, s), 7.30-7.20(2H, m), 7.91(1H, d, J=2.7Hz), 7.74(1H, d, J=1.5Hz), 7.67(1H, dd, J=8.7, 2.4Hz), 6.49(1H, t, J=2.4Hz), 3.44(3H, s), 1.89(3H, s)

[0110] Synthesis Example 1-1-5: Preparation of N,N'-dimethyl-3-(1H-pyrazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)isonicotinimidamide (Compound No. 20) N-((3-(1H-pyrazol-1-yl)pyridin-4-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (0.15 g, 0.45 mmol) prepared in Synthesis Example 1-1-2 was dissolved in N,N-dimethylformamide (3 mL), sodium hydride (content 55%, 22 mg, 0.50 mmol) was added, and the mixture was stirred at room temperature for 10 minutes, after which methyl iodide (30 μL, 0.40 mmol) was added and stirred at the same temperature for 30 minutes. Further sodium hydride (content 55%, 22 mg, 0.50 mmol) was added, and the mixture was stirred at room temperature for 10 minutes, after which methyl iodide (30 μL, 0.40 mmol) was added and stirred at the same temperature for 2.5 hours. Water was added, and the mixture was extracted twice with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure with an evaporator. The resulting crude product was purified by silica gel chromatography to obtain the target product (31 mg, 18.8%, white solid). 8.90(1H, s), 8.45(1H, d, J=4.8Hz), 8.29(1H, d, J=2.4Hz), 8.16(1H, s), 7.78(1H, d, J=1.5Hz), 1H NMR(CDCl 3 ) δ7.59(1H, dd, J=8.4, 2.4Hz), 7.03(1H, d, J=4.8Hz), 6.78(1H, d, J=8.4Hz), 6.48(1H, t, J=2.1Hz), 3.12(3H, s), 2.57(3H, s)

[0111] Synthesis Example 1-1-6: Preparation of 3-(2H-1,2,3-triazol-2-yl)isonicotinonitrile 3-Chloroisonicotinitrile (1.50g, 7.22mmol) and 1H-1,2,3-triazole (1.50g, 14.44mmol) were dissolved in dimethylsulfoxide (20mL), cooled in a water bath, sodium hydride (0.98g, 21.77mmol) was added, and the mixture was stirred at 100°C for 2 hours. Water was added, and the mixture was extracted four times with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain 3-(2H-1,2,3-triazol-2-yl)isonicotinitrile (0.92g, 49.8%) and 3-(1H-1,2,3-triazol-1-yl)isonicotinitrile (0.92g, 9.6%). 3-(2H-1,2,3-triazol-2-yl)isonicolinonitrile 1H NMR (CDCl 3 ) δ9.50(1H, s), 8.77(1H, d, J=4.8Hz), 8.00(2H, s), 7.71(1H, d, J=5.1Hz) 3-(1H-1,2,3-triazol-1-yl)isonicotinonitrile 1H NMR (CDCl 3 ) δ9.25(1H, s), 8.92(1H, d, J=5.1Hz), 8.29(1H, d, J=1.2Hz), 7.98(1H, d, J=1.2Hz), 7,76(1H, d, 5,1Hz)

[0112] Synthesis Example 1-1-7: Preparation of 3-(2H-1,2,3-triazol-2-yl)-N-(5-trifluoromethyl)pyridin-2-yl)isonicotinimidamide (Compound No. 7) 5-(Trifluoromethyl)pyridin-2-amine (0.57 g, 3.51 mmol) was dissolved in N,N-dimethylformamide (12 mL), sodium hydride (content 55%, 0.17 g, 3.86 mmol) was added, and the mixture was stirred at room temperature for 1 hour. 3-(2H-1,2,3-Triazol-2-yl)isonicotinonitrile (0.60 g, 3.51 mmol) prepared in Synthesis Example 1-1-6 was added thereto, and the mixture was stirred at room temperature for 13 hours. Water was added, and the mixture was extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the target product (0.74 g, 63.3%). 1H NMR(CDCl 3 ) δ10.34(1H, broad), 9.08(1H, s), 8.80(1H, d, J=4.8Hz), 8.57(1H, s), 7.86(2H, s), 7.81(1H, dd, J=8.4, 2.4Hz), 7.54(1H, d, J=5.1Hz), 7.14(1H, d, J=8.7Hz), 6.23(1H, broad)

[0113] Synthesis Example 1-1-8: Preparation of N-((3-(2H-1,2,3-triazol-2-yl)pyridin-4-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (Compound No. 16) Acetic anhydride (7 mL) was added to 3-(2H-1,2,3-triazol-2-yl)-N-(5-trifluoromethyl)pyridin-2-yl)isonicotinimidamide (0.36 g, 1.08 mmol) prepared in Synthesis Example 1-1-7, and the mixture was stirred under reflux for 20 minutes. Acetic anhydride was distilled off under reduced pressure at the same temperature, and the obtained crude product was purified by silica gel chromatography to obtain the target product (0.26 g, 63.6%, white solid). 1H NMR(CDCl 3) δ13.33(1H, s), 9.34(1H, s), 8.76(1H, s), 8.71(1H, d, J=5.1Hz), 7.97(1H, d, J=6.9Hz), 7.78(2H, s), 7.43(1H, d, J=5.1Hz), 7.32(1H, d, J=8.4Hz), 2.09(3H, s)

[0114] Synthesis Example 1-2-1: Preparation of 2-(3-(1H-pyrazol-1-yl)pyridin-4-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 46) 3-(1H-pyrazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)isonicotinimidamide (0.20 g, 0.60 mmol) prepared in Synthesis Example 1-1-2 was dissolved in dichloromethane (10 mL), and iodobenzene diacetate (0.23 g, 0.72 mmol) was added and stirred at room temperature for 2 hours. Iodobenzene diacetate (0.23 g, 0.72 mmol) was further added and stirred at room temperature for 5 hours. After dichloromethane was distilled off under reduced pressure with an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the target product (0.12 g, 61.3%, white solid). 1H NMR (CDCl 3 ) δ8.88(1H, s), 8.86-8.77(2H, m), 8.07(1H, d, J=4.8Hz), 7.84(1H, d, J=9.3Hz), 7.75-7.64(3H, m), 6.49(1H, t, J=2.4Hz)

[0115] Synthesis Example 1-2-2: Preparation of 2-(3-(2H-1,2,3-triazol-2-yl)pyridin-4-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 48) 3-(2H-1,2,3-triazol-2-yl)-N-(5-trifluoromethyl)pyridin-2-yl)isonicotinimidamide (0.14 g, 0.75 mmol) prepared in Synthesis Example 1-1-7 was dissolved in dichloromethane (7 mL), and iodobenzene diacetate (0.16 g, 0.49 mmol) was added and stirred at room temperature for 45 minutes. Water was added, and the mixture was extracted twice with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the target product (0.10 g, 74.1%). 1H NMR (CDCl 3 ) δ9.03(1H, s), 8.89(1H, d, J=5.1Hz), 8.80(1H, s), 8.10(1H, d, J=5.1Hz), 7.85(2H, s), 7.82(1H, d, J=9.3Hz), 7.69(1H, dd, J=9.3, 1.8Hz)

[0116] Synthesis Example 1-3-1: Preparation of 2-(3-(1H-pyrazol-1-yl)pyridin-4-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1,3,5]triazin-4-one (Compound No. 61) 3-(1H-pyrazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)isonicotinimidamide (0.18 g, 0.54 mmol) prepared in Synthesis Example 1-1-2 was dissolved in dichloromethane (8 mL), 4-chlorophenyl chloroformate (200 μL, 1.45 mmol) was added, followed by triethylamine (400 μL, 5.42 mmol), and the mixture was stirred at room temperature for 1 hour. Thereafter, dichloromethane was distilled off with an evaporator, ethyl acetate (10 mL) was added, and the mixture was stirred under heating and reflux for 4 hours. After distilling off ethyl acetate under reduced pressure with an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the target product (0.16 g, 84.6%, white solid). 1H NMR (CDCl 3) δ9.37(1H, s), 8.87(1H, s), 8.11(1H, d, J=4.8Hz), 8.10(1H, dd, J=9.0, 2.4Hz), 7.94(1H, d, J=5.1Hz), 7.80(1H, d, J=2.4Hz), 7.58(1H, d, J=1.8Hz), 7.52(1H, d, J=9.3Hz), 6.46(1H, t, J=2.1Hz)

[0117] Synthesis Example 1-3-2: Preparation of 2-(3-(2H-1,2,3-triazol-2-yl)pyridin-4-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1,3,5]triazin-4-one (Compound No. 62) 3-(2H-1,2,3-triazol-2-yl)-N-(5-trifluoromethyl)pyridin-2-yl)isonicotinimidamide (0.16 g, 0.49 mmol) prepared in Synthesis Example 1-1-7 was dissolved in dichloromethane (10 mL), 4-chlorophenyl chloroformate (150 μL, 1.09 mmol) was added, followed by triethylamine (300 μL, 2.16 mL), and the mixture was stirred at room temperature for 12 hours. Then, dichloromethane was distilled off with an evaporator, ethyl acetate (15 mL) was added, and the mixture was stirred for 2 hours under heating and reflux. After ethyl acetate was distilled off under reduced pressure with an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the target product (0.13 g, 74.0%). 1H NMR (CDCl 3 ) δ9.39(1H, s), 9.19(1H, s), 8.85(1H, d, J=4.8Hz), 8.12(1H, dd, J=9.3, 2.4Hz), 7.92(1H, d, J=5.1Hz), 7.78(2H, s), 7.53(1H, d, J=9.0Hz)

[0118] Synthesis Example 2-1-1: Preparation of 3-(ethylthio)picolinonitrile 3-Chloropicolinonitrile (1.00g, 7.22mmol) and ethyl mercaptan (0.59mL, 7.98mmol) were dissolved in N,N-dimethylformamide (10mL), cooled in an ice bath, sodium hydride (0.35g, 8.02mmol) was added, and the mixture was stirred at room temperature for 1.5 hours. Water was added, and the mixture was extracted three times with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the target product (1.11g, 93.6%, pale yellow oil). 1H NMR (CDCl 3 ) δ8.49(1H, dd, J=4.5, 1.2Hz), 7.75(1H, dd, J=8.4, 1.5Hz), 7.43(1H, dd, J=8.1, 4.5Hz), 3.06(2H, q, J=7.5Hz), 1.38(1H, t, J=7.5Hz)

[0119] Synthesis Example 2-1-2: Preparation of 3-(ethylthio)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 36) 5-(trifluoromethyl)pyridin-2-amine (1.09 g, 6.72 mmol) was dissolved in N,N-dimethylformamide (16 mL), sodium hydride (content 55%, 0.33 g, 7.56 mmol) was added, and the mixture was stirred at room temperature for 15 minutes. 3-(ethylthio)picolinonitrile (1.11 g, 6.76 mol) prepared in Synthesis Example 2-1-1 was added thereto, and the mixture was stirred at the same temperature for 5 hours, after which water was added, and the mixture was extracted twice with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the target product (0.90 g, 41.0%, white solid). 1H NMR (CDCl 3) δ10.04(1H, broad), 8.63(1H, s), 8.35(1H, dd, J=4.5, 1.2Hz), 7.91(1H, broad), 7.84(1H, dd, J=8.4, 2.4Hz), 7.71(1H, dd, J=8.4, 1.2Hz), 7.43(1H, d, J=8.7Hz), 7.32(1H, dd, J=8.1, 4.5Hz), 2.92(2H, q, J=7.5Hz), 1.41(3H, t, J=7.5Hz)

[0120] Synthesis Example 2-1-3: Preparation of 3-(ethylthio)-5-(4-(trifluoromethyl)phenyl)picolinonitrile 5-Bromo-3-(ethylthio)picolinonitrile (0.48 g, 1.97 mmol) prepared by the method described in WO2017016922, p.57 was dissolved in 1,4-dioxane (25 mL), the inside of the system was degassed with a pump, replaced with nitrogen, dichlorobis(triphenylphosphine)palladium(II) (0.14 g, 0.20 mmol) was added, and the mixture was heated and stirred at 60 ° C. for 10 minutes under a nitrogen atmosphere. Then, (4-(trifluoromethyl)phenyl)boronic acid (0.45 g, 2.37 mmol) and 2M aqueous sodium carbonate solution (5 mL) were added, degassed again, replaced with nitrogen, and stirred under reflux for 2 hours. After cooling, ethyl acetate and water were added, and unnecessary substances were removed by filtration using a filter aid. Water was further added to the filtrate, and the mixture was extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure using an evaporator. The resulting crude product was purified by silica gel chromatography to obtain the desired product (0.60 g, 98.6%). 1H NMR (CDCl 3 ) δ8.69(1H, d, J=1.8Hz), 7.87(1H, d, J=2.1Hz), 7.80(2H, d, J=8.4Hz), 7.70(2H, d, J=8.4Hz), 3.13(1H, q, J=7.5Hz), 1.43(3H, t, J=7.5Hz)

[0121] Synthesis Example 2-1-4: Preparation of 3-(ethylthio)-5-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 138) 5-(trifluoromethyl)pyridin-2-amine (106 mg, 0.65 mmol) was dissolved in N,N-dimethylformamide (4 mL), sodium hydride (content 55%, 31 mg, 0.71 mmol) was added, and the mixture was stirred at room temperature for 15 minutes. 3-(ethylthio)-5-(4-(trifluoromethyl)picolinonitrile (200 mg, 6.49 mol) prepared in Synthesis Example 2-1-3 was added thereto, and the mixture was stirred at room temperature for 16 hours, after which water was added and the mixture was extracted twice with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure with an evaporator. The crude product obtained was purified by silica gel chromatography, and the product was suspended in a mixture of ethyl acetate and hexane, filtered, and the target product was obtained. 1H NMR (CDCl 3 ) δ10.07(1H, broad), 8.65(1H, s), 8.55(1H, d, J=1.8Hz), 7.86(1H, dd, J=8.4Hz, 2.4Hz), 7.84(1H, d, J=2.1Hz), 7.78(2H, d, J=8.1Hz), 7.72(2H, d, J=8.1Hz), 7.46(1H, d, J=8.4Hz), 2.97(2H, q, J=7.5Hz), 1.46(3H, t, J=7.5Hz)

[0122] Synthesis Example 2-1-5: Preparation of 3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 139) 3-(ethylthio)-5-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (0.27 g, 0.57 mmol) prepared in Synthesis Example 2-1-4 was dissolved in dichloromethane (5.5 mL), 3-chloroperbenzoic acid (65%, 0.31 g, 1.15 mmol) was added, and the mixture was stirred at room temperature for 18 hours. An aqueous solution of sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure using an evaporator. The crude product obtained was purified by silica gel chromatography to obtain the target product (0.26 g, 91.5%). 1H NMR (CDCl 3 ) δ10.17(1H, broad), 9.05(1H, d, J=2.1Hz), 8.71(1H, d, J=1.5Hz), 8.69(1H, s), 7.95-7.75(6H, m), 7.20(1H, d, J=2.4Hz), 4.05(2H, q, J=7.5Hz), 1.42(3H, t, J=7.5Hz)

[0123] Synthesis Example 2-1-6: Preparation of 3-(ethylthio)-5-(2H-1,2,3-triazol-2-yl)picolinonitrile 5-Bromo-3-(ethylthio)picolinonitrile (1.00 g, 4.11 mmol) prepared by the method described in WO2017016922, p.57 was dissolved in N,N-dimethylformamide (10 mL), 1H-1,2,3-triazole (0.31 g, 4.49 mmol) and potassium carbonate (0.85 g, 6.15 mmol) were added, and the mixture was stirred at 80 ° C. for 5 hours. After cooling, water was added, and the mixture was extracted twice with ethyl acetate and washed with saturated saline. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the target product (0.49 g, 51.5%). 1H NMR (CDCl 3) δ9.21(1H, d, J=2.4Hz), 8.36(1H, d, J=2.1Hz), 7.93(2H, s), 3.17(2H, q, J=7.5Hz), 1.47(3H, t, J=7.5Hz)

[0124] Synthesis Example 2-1-7: Preparation of 3-(ethylthio)-5-(2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 102) 5-(trifluoromethyl)pyridin-2-amine (130 mg, 0.80 mmol) was dissolved in N,N-dimethylformamide (4 mL), sodium hydride (content 55%, 35 mg, 0.89 mmol) was added, and the mixture was stirred at room temperature for 15 minutes. 3-(ethylthio)-5-(2H-1,2,3-triazol-2-yl)picolinonitrile (186 mg, 0.80 mol) prepared in Synthesis Example 2-1-6 was added thereto, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction product, extracted with ethyl acetate, washed with saturated saline, and the obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure with an evaporator. The obtained crude product was purified by silica gel chromatography, and the product was suspended in a mixture of ethyl acetate and hexane, filtered, and the target product (92 mg, 29.1%) was obtained. 1H NMR (CDCl 3 ) δ10.06(1H, broad), 9.08(1H, d, J=2.1Hz), 8.65(1H, s), 8.40(1H, d, J=2.1Hz), 7.90(2H, s), 7.86(1H, dd, J=8.7, 2.7Hz), 7.45(1H, d, J=8.4Hz), 3.02(2H, q, J=7.5Hz), 1.48(3H, t, J=7.5Hz)

[0125] Synthesis Example 2-1-8: Preparation of 3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 103) 3-(ethylthio)-5-(2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (62 mg, 0.16 mmol) prepared in Synthesis Example 2-1-7 was dissolved in dichloromethane (2.5 mL), 3-chloroperbenzoic acid (65%, 86 g, 0.32 mmol) was added, and the mixture was stirred at room temperature for 2 hours. An aqueous solution of sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure using an evaporator. The crude product obtained was purified by silica gel chromatography to obtain the target product (45 mg, 67.1%). 1H NMR (CDCl 3 ) δ9.55(1H, d, J=2.4Hz), 9.18(1H, d, J=1.8Hz), 8.68(1H, s), 8.05-7.92(3H, m), 7.88(1H, dd, J=8.7Hz, 2.1Hz), 7.20(1H, d, J=8.7Hz), 4.07(2H, q, J=7.5Hz), 1.44(3H, t, J=7.5Hz)

[0126] Synthesis Example 2-1-9: Preparation of 3-chloro-5-(dimethylamino)picolinonitrile 3,5-Dichloropicolinonitrile (1.00g, 5.78mmol) was dissolved in N,N-dimethylformamide (10mL), 50% dimethylamine aqueous solution (1.21mL, 11.56mmol) was added, and the mixture was stirred at room temperature for 20 hours. Water was added to the reaction product, which was then extracted twice with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure using an evaporator. The resulting crude product was purified by silica gel chromatography to obtain the target product (0.70g, 66.7%). 1H NMR (CDCl 3 ) δ8.01(1H, d, J=2.7Hz), 6.88(1H, d, J=2.7Hz), 3.10(3H, s)

[0127] Synthesis Example 2-1-10: Preparation of 5-(dimethylamino)-3-(ethylthio)picolinonitrile 3-Chloro-5-(dimethylamino)picolinonitrile (0.70 g, 3.85 mmol) prepared in Synthesis Example 2-1-9 was dissolved in N,N-dimethylformamide (14 mL), ethyl mercaptan (0.92 mL, 3.92 mmol) was added, and sodium hydride (55%, 0.19 g, 4.29 mmol) was added under ice cooling and stirred. After returning to room temperature and stirring at the same temperature for 3 hours, water was added to the reaction product, which was extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure with an evaporator to obtain the crude target product (0.81 g). 1H NMR (CDCl 3 ) δ7.94(1H, d, J=2.7Hz), 6.81(1H, d, J=3.0Hz), 3.09(6H, s), 3.03(2H, q, J=7.5Hz), 1.35(3H, t, J=7.5Hz)

[0128] Synthesis Example 2-1-11: Preparation of 5-(dimethylamino)-3-(ethylthio)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 124) 5-(dimethylamino)-3-(ethylthio)picolinonitrile (0.20 g, 0.96 mmol) prepared in Synthesis Example 2-1-10 was dissolved in toluene (10 mL), and trimethylaluminum (1.8 M toluene solution, 1.0 mL, 3.92 mmol) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. Then, 5-(trifluoromethyl)pyridin-2-amine (0.16 g, 0.96 mmol) was added, and the mixture was stirred at 70° C. for 6 hours. Water was added to the reaction product, and the mixture was extracted twice with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then distilled under reduced pressure with an evaporator to obtain the target product (73 mg, 21%). 1H NMR (CDCl 3) δ9.98(1H, broad), 8.58(1H, s), 7.89(1H, d, J=1.8Hz), 7.80(1H, dd, J=8.4Hz, 2.4Hz), 7.42(1H, broad), 6.82(1H, d, J=2.4Hz), 3.09(6H, s), 2.89(2H, q, J=7.5Hz), 1.44(3H, t, J=7.5Hz)

[0129] Synthesis Example 2-2-1: Preparation of 2-(3-(ethylthio)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 53) 3-(ethylthio)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (0.38 g, 1.16 mmol) prepared in Synthesis Example 2-1-2 was dissolved in dichloromethane (12 ml), and iodobenzene diacetate (0.39 g, 1.22 mmol) was added and stirred at room temperature for 10 hours. After distillation under reduced pressure with an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the target product (0.19 g, 49.1%). 1H NMR (CDCl 3 ) δ9.06(1H, s), 8.60(1H, dd, J=4.5, 1.2Hz), 7.98(1H, d, J=9.3Hz), 7.76(1H., d, J=8.1, 1.5Hz), 7.72(1H, dd, J=9.3, 1.8Hz), 7.37(1H, dd, J=8.1, 4.5Hz), 3.02(2H, q, J=7.5Hz), 1.40(3H, t, J=7.5Hz)

[0130] Synthesis Example 2-2-2: Preparation of 2-(3-(ethylsulfinyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 54) and 2-(3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 55) 2-(3-(ethylthio)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (0.13 g, 0.40 mmol) prepared in Synthesis Example 2-2-1 was dissolved in dichloromethane (10 mL), 3-chloroperbenzoic acid (65%, 0.16 g, 0.60 mmol) was added, and the mixture was stirred at room temperature for 20 minutes. After distilling off dichloromethane under reduced pressure using an evaporator, the resulting crude product was purified by silica gel chromatography to obtain 2-(3-(ethylsulfinyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (6.4 mg, 4.7%) and 2-(3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (95 mg, 66.5%). compound 54 1H NMR (CDCl 3 ) δ9.04(1H, s), 8.93(1H, s), 8.63(1H, dd, J=8.1, 1.5Hz), 7.98(1H, d, J=9.3Hz), 7.79(1H, dd, J=9.3, 1.8Hz), 7.70(1H, dd, J=8.1, 4.8Hz), 3.46(1H, m), 3.00(1H, m), 1.39(3H, t, J=7.5Hz) compound 55 1H NMR (CDCl 3 ) δ9.07-8.98(2H, m), 8.55(1H, dd, J=8.1, 1.8Hz), 7.94(1H, d, J=9.6Hz), 7.76(1H, dd, J=9.6, 1.8Hz), 7.68(1H, dd, J=7.8, 4.5Hz), 3.96(2H, q, J=7.5Hz), 1.41(3H, t, J=7.5Hz)

[0131] Synthesis Example 2-2-3: Preparation of 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 176) 3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (51 mg, 0.10 mmol) prepared in Synthesis Example 2-1-5 was dissolved in dichloromethane (2.5 mL), and iodobenzene diacetate (98 mg, 0.30 mmol) was added and stirred at room temperature for 18 hours. After distillation under reduced pressure with an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the target product (37 mg, 72.8%). 1H NMR (CDCl 3 ) δ9.23(1H, d, J=2.1Hz), 9.02(1H, s), 8.74(1H, d, J=2.1Hz), 7.96(1H, d, J=9.3Hz), 7.89-7.79(4H, m), 7.78(1H, dd, J=9.3Hz, 1.5Hz), 4.05(2H, q, J=7.5Hz), 1.46(3H, t, J=7.5Hz)

[0132] Synthesis Example 2-2-4: Preparation of 2-(3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 181) 3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (0.10 g, 0.24 mmol) prepared in Synthesis Example 2-1-8 was dissolved in dichloromethane (3 mL), and iodobenzene diacetate (0.23 g, 0.71 mmol) was added and stirred at room temperature for 16 hours. After distillation under reduced pressure with an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the target product (72 mg, 72.4%). 1H NMR (CDCl 3) δ9.74(1H, d, J=2.1Hz), 9.20(1H, d, J=2.1Hz), 9.02(1H,s), 8.01-7.92(3H, m), 7.78(1H, dd, J=9.3Hz, 1.5Hz), 4.06(2H, q, J=7.5Hz), 1.47(3H, t, J=7.5Hz)

[0133] The compounds of the present invention shown in Table 8, the compounds of the present invention shown in Table 9, the compounds of the present invention shown in Table 10, the compounds of the present invention shown in Table 11, the compounds of the present invention shown in Table 12, the compounds of the present invention shown in Table 13, the compounds of the present invention shown in Table 14, the compounds of the present invention shown in Table 15, the compounds of the present invention shown in Table 16, the compounds of the present invention shown in Table 17, the compounds of the present invention shown in Table 18, the compounds of the present invention shown in Table 19, the compounds of the present invention shown in Table 20, the compounds of the present invention shown in Table 21, the compounds of the present invention shown in Table 22, the compounds of the present invention shown in Table 23, the compounds of the present invention shown in Table 24, the compounds of the present invention shown in Table 25, the compounds of the present invention shown in Table 26, the compounds of the present invention shown in Table 1 The H-NMR data and melting points are shown in Table 14. Note that some of the NMR data does not detect amidine protons. [ka]

[0134] [Table 8-1]

[0135] [Table 8-2]

[0136] [ka]

[0137] [Table 9-1]

[0138] [Table 9-2]

[0139] [Table 9-3]

[0140]

Table 9-4

[0141]

change

[0142]

Table 10

[0143]

change

[0144]

Table 11

[0145]

change

[0146]

Table 12

[0147]

change

[0148]

Table 13

[0149]

Table 14-1

[0150]

Table 14-2

[0151]

Table 14-3

[0152]

Table 14-4

[0153]

Table 14-5

[0154]

Table 14-6

[0155]

Table 14-7

[0156]

Table 14-8

[0157]

Table 14-9

[0158]

Table 14-10

[0159]

Table 14-11

[0160]

Table 14-12

[0161]

Table 14-13

[0162]

Table 14-14

[0163]

Table 14-15

[0164]

Table 14-16

[0165]

Table 14-17

[0166]

Table 14-18

[0167]

Table 14-19

[0168]

Table 14-20

[0169]

Table 14-21

[0170] [Table 14-22]

[0171] [Table 14-23]

[0172] [Table 14-24]

[0173] [Table 14-25]

[0174] <Formulation examples> Examples of agricultural chemical formulations containing the compounds of the present invention as active ingredients are given below. Formulation Example 1 [Wettable powder] Compound 30% by weight Clay 30% by weight Diatomaceous earth 35% by weight Sanex P252 4% by weight (Calcium lignosulfonate: Trade name of Nippon Paper Industries Co., Ltd.) Solpol 8070 1% by weight (Sodium lauryl sulfate: trade name of Toho Chemical Industry Co., Ltd.) The above ingredients were mixed uniformly and pulverized to obtain wettable powders.

[0175] Formulation Example 2 [Powder] Compound 2% by weight Clay 90% by weight Talc 7% by weight Calcium stearate 1% by weight The ingredients were mixed uniformly to obtain a powder.

[0176] Formulation Example 3 [Emulsion] Compound 20% by weight N,N-Dimethylformamide 20% by weight T-SOL 150 50% by weight (Aromatic solvent: Product name of JXTG Energy Corporation) New Calgen CL-H 10% by weight (POE alkyl phenyl ether: Product name of Takemoto Yushi Co., Ltd.) The above components were uniformly mixed and dissolved to obtain an emulsion.

[0177] Formulation Example 4 [Emulsion 2] Compound 5% by weight Xylene 42.5% by weight DMSO 42.5% by weight New Calgen 2003 10% by weight (Mixture of POE allyl phenyl ether formaldehyde condensate and metal salt of alkyl benzene sulfonic acid: Product name of Takemoto Yushi Co., Ltd.) The above components were uniformly mixed and dissolved to obtain an emulsion. Formulation Example 5 [Granules] Compound 5% by weight Bentonite 40% by weight Talc 10% by weight Clay 43% by weight Sun Extract P252 2% by weight (Calcium lignosulfonate: Trade name of Nippon Paper Industries Co., Ltd.) The above components were uniformly pulverized and mixed, water was added and kneaded well, and then granulated and dried to obtain granules.

[0178] Formulation Example 6 [Flowable Agent] Compound 25% by weight Solpol 7556 5% by weight (POE styryl phenyl ether sulfate: Product name of Toho Chemical Industry Co., Ltd.) Propylene glycol 6% by weight Bentonite 1% by weight 1% aqueous solution of xanthan gum 3% by weight Water 60% by weight The entire amount of the above formulation, excluding the 1% xanthan gum aqueous solution and an appropriate amount of water, was premixed and then pulverized in a wet pulverizer. The 1% xanthan gum aqueous solution and the remaining water were then added to the pulverized mixture to obtain a 100% by weight flowable preparation.

[0179] Formulation Example 7 [Granules] Compound 5% by weight Bentonite 40% by weight Talc 10% by weight Clay 43% by weight Sanex P252 2% by weight (Calcium lignosulfonate: Trade name of Nippon Paper Industries Co., Ltd.) The above ingredients were uniformly pulverized and mixed, water was added, the mixture was thoroughly kneaded, and then the mixture was granulated and dried to obtain granules.

[0180] <Biological test example> The following tests demonstrate the control efficacy of the compounds of the present invention against certain pests. "Control efficacy" refers to the inhibition of development (including mortality) of invertebrate pests, which significantly reduces feeding. The pest control protection achieved by the compounds is not, however, limited to these species. Compound numbers refer to compounds in Tables 8-13.

[0181] Biological test example 1: Cotton aphid (Aphis gossypii) control test (leaf spray treatment) Cucumber leaves were cut into pieces 3.5 cm in diameter and placed on absorbent cotton moistened with water. Two adult cotton aphids were released onto the leaves and allowed to lay offspring for 24 hours, after which the adults were removed. 2 mL of a diluted solution of the test compound, diluted with water to 200 ppm, was sprayed onto the cucumber leaves using a spray tower. After air drying, the leaves were placed in a plastic cup together with the absorbent cotton, covered, and reared in a constant temperature room at 25°C. Five days after treatment, the animals were observed for survival and death, and the mortality rate was calculated. As a result, the compounds of the present invention 1, 2, 3, 4, 5, 7, 8, 9, 10, 11, 12, 14, 17, 18, 19, 20, 26, 27, 28, 29, 30, 31, 42, 43, 45, 46, 48, 49, 50, 51, 53, 54, 55, 59, 61, 62, 66, 80, 85, 86, 87, 91, 103, 10 5, 106, 108, 110, 111, 112, 114, 120, 123, 125, 127, 135, 148, 150, 152, 156, 160, 170, 173, 174, 175, 177, 180, 181, 199, 201, 204, 207, 209, 215, and 220 showed mortality rates of over 80%.

[0182] Biological test example 2: Cotton aphid (Aphis gossypii) control test (root immersion treatment) One cucumber seedling (cotyledon stage) was fixed with urethane so that the roots were immersed in a vial (inner diameter 2.7 cm x 6 cm) containing 10 mL of a 3.1 ppm solution diluted with water. One day after immersion, five first-instar cotton aphid larvae were released and reared in a constant temperature room at 25°C. Five to seven days after release, the insects were checked for survival and death, as well as for abnormalities. As a result, compounds 2, 3, 7, 14, 20, 29, 45, 46, 48, 51, 53, 55, 62, 85, 91, 103, 105, 106, 108, 111, 120, 170, 173, 180, and 199 of the present invention showed insect mortality rates of 80% or more.

[0183] Biological test example 3: Bemisia tabaci control test (foliage spray treatment) Cucumber leaves were cut to a diameter of 6.0 cm and placed on absorbent cotton moistened with water. 2 mL of a diluted solution of the test compound, diluted with water to 200 ppm, was sprayed onto the cucumber leaves using a spray tower. After air drying, the cucumber leaves were placed in plastic cups, and 20 adult female Bemisia tabaci were released into the cups. The cups were then covered and reared in a constant temperature room at 25°C. Five days after treatment, the number of live or dead insects was observed, and the mortality rate was calculated. As a result, compounds 13, 156, 196, 204, 209, and 215 showed mortality rates of over 80%.

[0184] Biological test example 4: Diamondback moth (Plutella xylostella) control test (leaf immersion treatment) Cabbage leaves were cut into pieces with a diameter of 7.0 cm, and the pieces were immersed in 20 mL of a diluted solution of the test compound diluted with water to 200 ppm, and then air-dried. After air-drying, the pieces were placed in plastic cups, and 10 third-instar larvae of the diamondback moth were released into them. The cups were then covered and reared in a constant temperature room at 25°C. Five days after treatment, the survival and death of the larvae was observed, and the mortality rate was calculated. As a result, compounds 7, 8, 37, 46, 48, 55, 61, 69, 78, 91, 100, 101, 103, 105, 106, 108, 109, 110, 111, 112, 113, 114, 120, 125, 127, 128, 129, 131, 137, 139, 140, 142, 152, 158, 161, 175, 176, 177, 178, 180, 181, 188, 191, 195, 199, 200, 201, 204, 205, 207, 209, 211, 213, 214, 215, 216, 217, 218, 219, and 220 of the present invention showed insect mortality rates of 80% or more.

[0185] Biological test example 5: Control test of brown planthopper (Nilaparvata lugens) (stems and leaves immersion treatment) Ten rice seedlings were taken, immersed in 20 mL of a solution of the test compound diluted with water to 200 ppm, and air-dried. After air-drying, the seedlings were held in a glass cylinder (inner diameter 4.5 cm x 14 cm) using urethane and placed in a plastic cup containing 40 mL of water. Third-instar larvae of the brown planthopper were released into the seedlings, covered with drug-wrapping paper, and reared in a constant temperature room at 25°C. Five days after treatment, the larvae were observed for survival and death, and the mortality rate was calculated. As a result, compounds 1, 2, 3, 4, 5, 7, 10, 11, 14, 16, 18, 19, 20, 26, 29, 31, 42, 43, 44, 45, 46, 48, 49, 50, 51, 53, 55, 59, 61, 85, 86, 90, 91, 98, 103, 106, 152, 170, 176, 181, and 215 of the present invention showed insect mortality rates of 80% or more.

[0186] Biological Test Example 6: White-backed planthopper (Sogatella furcifera) control test (root immersion treatment) Ten rice seedlings were taken and held in a glass cylinder (inner diameter 4.5 cm x 14 cm) using urethane, and placed in a plastic cup containing 40 mL of a drug solution diluted with water to a concentration of 3.1 ppm. Two days later, ten third-instar larvae of the white-backed planthopper were released into the glass cylinder, which was then covered with drug-wrapping paper and reared in a constant temperature room at 25°C. Seven days after treatment, the larvae were observed for survival and death, and the mortality rate was calculated. As a result, the compounds of the present invention 2, 3, 4, 16, 20, 29, 42, 47, 48, 53 and 55 showed a mortality rate of 80% or more.

[0187] Biological Test Example 7: Spodoptera litura control test (stems and leaves immersion treatment) Cabbage leaves were cut into pieces with a diameter of 5.0 cm, and the pieces were immersed in 20 mL of a diluted solution of the test compound diluted with water to 200 ppm, and air-dried. After air-drying, the pieces were placed in plastic cups, and five second-instar larvae of Spodoptera litura were released into them. The cups were then covered and reared in a constant temperature room at 25°C. Five days after treatment, the survival and death of the larvae was observed, and the mortality rate was calculated. As a result, compounds 91, 100, 103, 106, 120, 127, 131, 133, 137, 139, 140, 142, 148, 174, 175, 176, 177, 178, 180, 181, 200, 201, 204, 205, 207, 209, 211, 213, 214, 215, 216, 217, 219, and 220 of the present invention showed insect mortality rates of 80% or more.

[0188] Biological test example 8: Control test of Phyllotreta striolata (stems and leaves immersion treatment) Cabbage leaves were cut into pieces with a diameter of 2.8 cm, and the pieces were immersed in 20 mL of a diluted solution of the test compound diluted with water to 200 ppm, and then air-dried. After air-drying, the pieces were placed in plastic cups, and five adult striped flea beetles were released into them. The cups were then covered and reared in a constant temperature room at 25°C. Two days after treatment, the number of adults alive or dead was observed, and the mortality rate and the degree of feeding damage were calculated. As a result, compounds 91, 100, 101, 103, 106, 127, 131, 133, 137, 139, 140, 142, 148, 174, 175, 176, 177, 181, and 205 of the present invention showed an insect mortality rate of 80% or more or a feeding damage level of 10% or less.

Claims

1. A compound represented by formula (2), a salt thereof, or an N-oxide thereof: 【Chemistry 1】 [In formula (2), G ２ (G ２ -1), 【Chemistry 2】 R １ , R ２ , R ３ and R ４ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo(C １ ~C ６ ) alkoxy, halo (C １ ~C ６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl, halo(C １ ~C ６ ) alkylsulfonyl, (C=O)NY １ Y ２ Or -NY １ Y ２ represents A １ is C-R Ｃ or N, A ２ is C-R Ｅ or N, １ , A ２ One of them is N and the other is C-R Ｃ or C-R Ｅ It is.) R Ａ is a group selected from the group consisting of C1-C3 alkoxy, halo(C1-C3)alkoxy, C1-C3 alkylthio, halo(C1-C3)alkylthio, C1-C3 alkylsulfonyl, halo(C1-C3)alkylsulfonyl, 1H-pyrazol-1-yl, and 2H-1,2,3-triazol-2-yl; R Ｂ , R Ｃ , R Ｄ and R Ｅ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C ３ ~C ６ cycloalkyl, substituted by U (C ３ ~C ６ ) cycloalkyl, C １ ~C ６ Alkoxy, halo(C １ ~C ６ ) an alkoxy group, a phenoxy group optionally substituted with up to five Z groups; １ ~C ６ Alkylthio, halo(C １ ~C ６ ) alkylthio, C １ ~C ６ Alkyl sulfinyl, halo(C １ ~C ６ ) alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylsulfonyl, (C=O)NY ３ Y ４ , -NY ３ Y ４ , cyano, nitro, a phenyl group which may be substituted with up to five Z's, a pyridyl group which may be substituted with up to four Z's, a pyrimidyl group which may be substituted with up to three Z's, a pyrazyl group which may be substituted with up to three substituents, a pyridazyl group which may be substituted with up to three Z's, a thienyl group which may be substituted with up to three Z's, a furanyl group which may be substituted with up to three Z's, or V, V represents a structure represented by (V-1), (V-2), (V-3), (V-4), (V-5) or (V-6); 【Chemistry 3】 Z is independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo(C １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, halo(C １ ~C ６ ) alkylthio, C １ ~C ６ Alkyl sulfinyl, halo(C １ ~C ６ ) alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylsulfonyl, -NY ５ Y ６ , cyano or nitro; Q2, Q3 or Q4 represents the number of substituents of Z; Q2 represents an integer of 0, 1 or 2; Q3 represents an integer of 0, 1, 2 or 3; Q4 represents an integer of 0, 1, 2, 3 or 4; When Q2, Q3 or Q4 represents an integer of 2 or more, a plurality of Z's may be the same or different from each other; Y １ , Y ２ , Y ３ , Y ４ , Y ５ , Y ６ Each independently represents a hydrogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkylcarbonyl, halo(C １ ~C ６ ) alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, halo(C １ ~C ６ ) alkoxycarbonyl, C １ ~C ６ Alkyl sulfonyl or halo(C １ ~C ６ ) alkylsulfonyl; U is cyano, -C(O)OH or -C(O)NH ２ represents Here, R Ｂ , R Ｃ , R Ｄ and R Ｅ is such that at least one of them is a phenyl group which may each independently be substituted with up to 5 Z's, or a group represented by (V-2), (V-4), (V-5) or (V-6).]

2. In formula (2), R １ , R ２ , R ３ and R ４ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo(C １ ~C ６ ) alkoxy, halo (C １ ~C ６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl or halo(C １ ~C ６ ) alkylsulfonyl; R Ｂ , R Ｃ , R Ｄ and R Ｅ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C ３ ~C ６ cycloalkyl, substituted by U (C ３ ~C ６ ) cycloalkyl, C １ ~C ６ Alkoxy, halo(C １ ~C ６ ) an alkoxy group, a phenoxy group optionally substituted with up to five Z groups; １ ~C ６ Alkylthio, halo(C １ ~C ６ ) alkylthio, C １ ~C ６ Alkyl sulfinyl, halo(C １ ~C ６ ) alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) alkylsulfonyl, -NY ３ Y ４ , cyano, nitro or V, V represents a structure represented by (V-1), (V-2), (V-3), (V-4), (V-5) or (V-6); 【Chemistry 4】 The compound according to claim 1, or a salt thereof, or an N-oxide thereof.

3. A １ is N, and A ２ is C-R Ｅ 3. The compound according to claim 1 or 2, or a salt thereof, or an N-oxide thereof:

4. A １ is C-R Ｃ And A ２ The compound according to claim 1 or 2, or a salt thereof, or an N-oxide thereof, wherein

5. A １ is C-R Ｃ And A ２ is N and R Ａ C １ ~C ３ alkylsulfonyl, R Ｂ , R Ｄ is a hydrogen atom, R Ｃ is a phenyl group optionally substituted with up to five Z's, or a group represented by (V-2), (V-4), (V-5) or (V-6), or an N-oxide of the compound or salt thereof according to claim 1 or 2.

6. A compound selected from the group consisting of the following, or a salt thereof, or an N-oxide thereof: 2-(3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 180), 2-(3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 181), 2-(3-(ethylsulfonyl)-5-(2-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 174), 2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 175), 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 176), 2-(5-(2,4-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine, 2-(5-(3,5-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 178), 2-(3-(ethylsulfonyl)-5-(2-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine, 2-(3-(ethylsulfonyl)-5-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound number 214), and 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 177)

7. A pest control agent comprising the compound or a salt thereof, or an N-oxide thereof according to any one of claims 1 to 6 as an active ingredient.

8. The pesticide according to claim 7, further comprising at least one component selected from the group consisting of a surfactant, a solid carrier, and a liquid carrier.

9. 9. The pesticide of claim 7 or 8, further comprising at least one other pesticide compound or agent.

10. The pest control agent according to any one of claims 7 to 9, wherein the pest is an agricultural or horticultural pest.

11. The pest control agent according to any one of claims 7 to 9, wherein the pest is an animal parasitic pest and is administered to animals or birds.

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