Pyrimidinyltriazole compound or its salt, and pest control agent and pest control method containing said compound as an active ingredient

Abstract

The present invention addresses the problem of providing a novel agricultural / horticultural pest control agent that is safe for honeybees and is effective for the control of pests. Provided is a compound represented by formula (I) or a salt thereof.

Description

[Technical field]

[0001] The present invention relates to a pyrimidinyltriazole compound or a salt thereof, and a pest control agent and a pest control method each containing the compound as an active ingredient. [Background technology]

[0002] Patent Document 1 describes that certain pyrimidinyl triazole compounds are useful as ectoparasite control agents for animals. Patent Document 2 describes that the pyrimidinyl triazole compounds are useful as agricultural and horticultural pest control agents. Patent Documents 3 to 24 describe that other pyrimidinyl triazole compounds are useful as agricultural and horticultural pest control agents or ectoparasite control agents for animals. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2017 / 192385 Brochure [Patent Document 2] International Publication No. 2019 / 170626 Brochure [Patent Document 3] International Publication No. 2019 / 197468 Brochure [Patent Document 4] International Publication No. 2019 / 201835 Brochure [Patent Document 5] International Publication No. 2019 / 202077 Brochure [Patent Document 6] International Publication No. 2019 / 206799 Brochure [Patent Document 7] International Publication No. 2019 / 215198 Brochure [Patent Document 8] International Publication No. 2020 / 002563 Brochure [Patent Document 9] International Publication No. 2020 / 053365 Brochure [Patent Document 10] International Publication No. 2020 / 079198 Brochure [Patent Document 11] International Publication No. 2020 / 094363 Brochure [Patent Document 12] International Publication No. 2020 / 182649 Brochure [Patent Document 13] International Publication No. 2020 / 188014 Brochure [Patent Document 14] International Publication No. 2020 / 188027 Brochure [Patent Document 15] International Publication No. 2020 / 193341 Brochure [Patent Document 16] International Publication No. 2020 / 212235 Brochure [Patent Document 17] International Publication No. 2021 / 013719 Brochure [Patent Document 18] International Publication No. 2021 / 013720 Brochure [Patent Document 19] International Publication No. 2021 / 069567 Brochure [Patent Document 20] International Publication No. 2021 / 069569 Brochure [Patent Document 21] International Publication No. 2021 / 083936 Brochure [Patent Document 22] International Publication No. 2021 / 099303 Brochure [Patent Document 23] International Publication No. 2021 / 110891 Brochure [Patent Document 24] International Publication No. 2021 / 122645 Brochure Summary of the Invention [Problem to be solved by the invention]

[0004] In the production of useful crops in the agricultural and horticultural fields, damage caused by pests is severe, and many agricultural and horticultural pest control agents that are effective against this are on the market. However, due to the emergence of pests resistant to existing drugs and the demand for drugs with properties suitable for various labor-saving application methods, the development of new agricultural and horticultural pest control agents remains one of the important issues in the agricultural and horticultural fields. Furthermore, in recent years, safety for useful insects, especially honeybees, has become a major issue to be resolved, and there is a demand for pest control agents that are safe for honeybees and effective against agricultural and horticultural pests. [Means for solving the problem]

[0005] Means for Solving the Problems The present inventors have conducted intensive research to develop a novel agricultural and horticultural pest control agent that is safe for honeybees, and as a result have found that the novel pyrimidinyltriazole compound or a salt thereof of the present invention is safe for honeybees and effective as an agricultural and horticultural pest control agent, thereby completing the present invention.

[0006] That is, the present invention is [1] Formula (I) [ka] or a salt thereof, [2] An agricultural and horticultural pest control agent comprising the compound or a salt thereof according to [1] as an active ingredient. [3] A method for using the agricultural and horticultural pest control agent according to [2], comprising applying an effective amount of the agricultural and horticultural pest control agent to a target plant or soil; [4] The present invention relates to a method for controlling agricultural and horticultural pests, which comprises applying an effective amount of the agricultural and horticultural pest control agent according to [2] to a target plant or soil. Effect of the Invention

[0007] The present invention provides a pyrimidinyltriazole compound or a salt thereof which is safe to honeybees and has an excellent effect as an agricultural and horticultural pest control agent. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] The pyrimidinyltriazole compound represented by formula (I) of the present invention can be produced in accordance with the production method described in Patent Document 1, for example, by the production method described below, but the production method of the compound of the present invention is not limited thereto.

[0009] Manufacturing method [ka]

[0010] As described in Patent Document 1, a compound represented by formula (II) is reacted with dimethylformamide dimethylacetal represented by formula (III) in the presence of an inert solvent to obtain a compound represented by formula (IV) (Step 1), and the compound is then reacted with a hydrazinopyrimidine compound represented by formula (V) in the presence of an acid catalyst and an inert solvent (Step 2) to produce the compound of the present invention represented by formula (I).

[0011] <Process 1> The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples of such inert solvents include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, toluene, and xylene, amides such as dimethylformamide, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, and hexamethylphosphoramide, halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride, and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, and halogenated hydrocarbons are particularly preferred. These inert solvents may be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited, and may be an amount that can dissolve the compound represented by formula (II), and may be appropriately selected within the range of 0.01 mol / L to 100 mol / L relative to the compound represented by formula (II).

[0012] The reaction temperature may be selected from the range of about -20 to 150°C, and preferably from 20°C to 100°C. The reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected from the range of several minutes to about 48 hours. After the reaction is completed, the target product is isolated from the reaction solution containing the compound represented by formula (IV) by a conventional method, and if necessary, purified using an appropriate purification method such as recrystallization, distillation, column chromatography, etc., to produce the compound represented by formula (IV). The compound represented by formula (IV) can also be subjected to step 2 without being isolated. In addition, since this reaction is an equimolar reaction, the respective reactants may be used in equimolar amounts, but any of the reactants may be used in excess.

[0013] <Process 2> The acid catalyst that can be used in this reaction may be any that promotes this reaction, and examples of the acid catalyst include organic acids such as formic acid, acetic acid, and propionic acid, and inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid. The amount of the acid catalyst used may be appropriately selected within a range of about 0.5 to 5 times the molar amount of the compound represented by formula (IV), and the acid catalyst may also be used as a solvent.

[0014] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, toluene, and xylene, amides such as dimethylformamide, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, and hexamethylphosphoramide, nitriles such as acetonitrile and propionitrile, organic acids such as formic acid, acetic acid, and propionic acid, halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride, and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, and cyclic ethers or organic acids are particularly preferred. These inert solvents may be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited, and may be an amount that can dissolve the compound represented by formula (IV), and may be appropriately selected within the range of 0.01 mol / L to 100 mol / L relative to the compound represented by formula (IV).

[0015] The reaction temperature may be selected from the range of about -20 to 150°C, and preferably from 20°C to 100°C. The reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected from the range of several minutes to about 48 hours. After the reaction is completed, the target product is isolated from the reaction system containing the compound of the present invention represented by formula (I) by a conventional method, and if necessary, purified by an appropriate purification method such as recrystallization, distillation, column chromatography, etc., to produce the compound of the present invention represented by formula (I). In addition, since this reaction is an equimolar reaction, each reactant may be used in equimolar amounts, but any of the reactants may be used in excess.

[0016] The salt of the compound represented by formula (I) of the present invention may be Inorganic acid salts such as hydrochlorides, sulfates, nitrates, and phosphates; Organic acid salts such as acetates, fumarates, maleates, oxalates, methanesulfonates, benzenesulfonates, and paratoluenesulfonates; and Salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium Examples include:

[0017] The compound represented by formula (I) or its salt of the present invention can be used as an agricultural and horticultural pest control agent. The pests that can be controlled include various agricultural and forestry pests, horticulture pests, grain storage pests, and sanitary pests that damage rice, fruit trees, vegetables, other crops, and ornamental plants. The above pests include insects, as well as mites and nematodes, and the following pests are specifically exemplified. Lepidoptera (Lepidoptera) pests include, for example, Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, Spodoptera exempta, Hyphantria cunea, Ostrinia furnacalis, Pseudaletia separata, Tinea translucens, Bactra furfurana, Parnara guttata, Marasmia exigua, Parnara guttata, Sesamia inferens, Brachmia triannulella, Monema flavescens, Trichoplusia ni, Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Cephonodes hylas, Helicoverpa armigera, Phalerodonta manleyi, Eumeta japonica, Pieris brassicae, Malacosoma neustria testacea, Stathmopoda masinissa, Cuphodes diospyrosella, Archipelago tortrix xylosteanus), Agrotis segetum, Tetramoera schistaceana, Papilio machaon hippocrates,

[0018] Endoclyta sinensis, Lyonetia prunifoliella, Phyllonorycter ringoneella, Cydia kurokoi, Eucoenogenes aestuosa, Lobesia botrana, Latoia sinica, Euzophera batangensis, Phalonidia mesotypa, Spilosoma imparilis, Glyphodes pyloalis, Olethreutes mori, Tineola bisselliella, Endoclyta excrescens, Nemapogon granellus, Synanthedon hector, Codling moth, Diamondback moth, Rice leaf borer, Southern pink borer, Scirpophaga incertulas, Grassland moth, Potato tuber moth, Potato leaf moth, Bead moth, Bead leaf moth, Rice leaf borer ... innotata), Xestia c-nigrum, Spodoptera depravata, Ephestia kuehniella, Angerona prunaria, Closteraanastomosis), soybean looper (Pseudoplusia includens), soybean pod moth (Matsumuraeses falcana), tobacco budworm (Helicoverpa assulta), silver moth (Autographa nigrisigna),

[0019] Agrotis ipsilon, Euproctis pseudoconspersa, Adoxophyes orana, Caloptilia theivora, Homona magnanima, Ephestia elutella, Eumeta minuscula, Clostera anachoreta, Heliothis maritima, Sparaganothis pilleriana, Busseola fusca, Euproctis subflava, Biston robustum, Tuta absoluta, Heliothis zea, Aedia leucomelas, Japanese pear moth (Narosoideus flavidorsalis), Japanese pear moth (Viminia rumicis), Japanese pear short moth (Bucculatrix pyrivorella), Japanese pear fruit moth (Grapholita molesta), Japanese pear leaf moth (Spulerina astaurota), Japanese pear meal moth (Ectomyelois pyrivorella), Japanese chilo borer moth (Chilo suppressalis), Japanese onion leaf moth (Acrolepiopsis sapporensis), Japanese meal moth (Plodia interpunctella), Japanese yellow meal moth (Hellula undalis), Japanese white moth (Sitotroga cerealella), Japanese cutworm moth (Spodoptera litura), Japanese tortrix moth (Eucosma aporema), Japanese rose moth (Acleris comariana), Japanese black moth (Scopelodes contractus), Orgyia thyellina, Spodoptera frugiperda, Ostrinia zaguliaevi, Naranga aenescens, Andracabipunctata), Grape moth (Paranthrene regalis), Grape wasp (Acosmeryx castanea), Grape leafminer moth (Phyllocnistis toparcha), Grape shrike moth (Endopiza viteana), Grape narrow-leaved moth (Eupoecillia ambiguella), Velvet bean caterpillar (Anticarsia gemmatalis), Narrow-leaved gray moth (Cnephasia cinereipalpana), Gypsy moth (Lymantria dispar), Pine moth (Dendrolimus spectabilis), Bean root moth (Leguminivora glycinivorella), Bean mealybug (Maruca testulalis), Bean pea leafminer moth (Matsumuraeses phaseoli),

[0020] Caloptilia soyella, citrus leafminer (Phyllocnistis citrella), Omiodes indicate, Archips fuscocupreanus, Acanthoplusia agnata, Bambalina sp., Carposina niponensis, Conogethes punctiferalis, Synanthedon sp.), peach leafminer moth (Lyonetia clerkella), common swallowtail butterfly (Papilio helenus), common yellow butterfly (Colias erate poliographus), black orca moth (Phalera flavescens), cabbage white butterfly (Pieris rapae crucivora), cabbage white butterfly (Pieris rapae), white tussock moth (Euproctis similis), mountain potato moth (Acrolepiopsis suzukiella), European corn borer (Ostrinia nubilalis), armyworm moth (Mamestra brassicae), mugwort geometries (Ascotis selenaria), mugwort spur moth (Phtheochroides clandestina), apple moth (Hoshinoa adumbratana), apple moth (Odonestis pruni japonensis, Triaena intermedia, Adoxophyes orana fasciata, Grapholita inopinata, Spironota ocellana, Spironota lechriaspis, Illiberis pruni, Argyresthia conjugella, Caloptilia zachrysa, Archips breviplicanus, Anomis flava, Pectinophora gossypiella, Notarcha derogata, Diaphania indica, Heliothis virescens, and Earias cupreoviridis) and others.

[0021] Hemiptera (Hemiptera) pests include, for example, Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, Aeschynteles maculatus, Creontiades pallidifer, Dysdercus cingulatus, Chrysomphalus ficus, Aonidiella aurantii, Graptopsaltria nigrofuscata, American long-horned stink bug (Blissusleucopterus), Icerya scale bug (Icerya purchasi), striped stink bug (Piezodorus hybneri), rice stink bug (Lagynotomus elongatus), rice leafhopper (Thaia subrufa), rice black stink bug (Scotinophara lurida), thorny long-horned aphid (Sitobion ibarae), Iwasaki stink bug (Stariodes iwasakii), pale scale insect (Aspidiotus destructor), pale-brown rice bug (Taylorilygus pallidulus), plum horn aphid (Myzus mumecola), plum white scale insect (Pseudaulacaspis prunicola), pea aphid (Acyrthosiphon pisum), spider bug (Anacanthocoris striicornis), black-spotted stink bug (Ectometopterus micantulus), large spurred spotted bug (Eysarcoris lewisi), large stink bug (Molipteryx fuliginosa), leafhopper (Cicadella viridis), red-veined aphid (Rhopalosophumrufiabdominalis), Olive scale (Saissetia oleate),

[0022] Trialeurodes vaporariorum, Aguriahana quercus, Lygus spp., Euceraphis punctipennis, Andaspis kashicola, Coccus pseudomagnoliarum, Cavelerius saccharivorus, Galeatus spinifrons, Macrosiphoniella sanborni, Aonidiella citrina, Halyomorpha mista, Stephanitis fasciicarina, Trioza camphorae), spider bug (Leptocorisa chinensis), chestnut psyllid (Trioza quercicola), walnut tail bug (Uhlerites latius), grape leaf hopper (Erythroneura comes), black legged stink bug (Paromius exiguus), black scale insect (Duplaspidiotus claviger), black leafhopper (Nephotettix nigropictus), black dust lizard (Halticiellus insularis), black planthopper (Perkinsiella saccharicida), black apple psylla (Psylla malivorella), mulberry psyllid (Anomomeura mori), mulberry mealybug (Pseudococcus longispinis), mulberry white scale (Pseudaulacaspis pentagona), mulberry cotton scale (Pulvinaria kuwacola), green grass bug (Apolygus lucorum), rice gourd long-horned bug (Togo hemipterus), cane aphid (Toxoptera aurantii), sugarcane mealybug (Saccharicoccussacchari), sugarcane aphid (Geoica lucifuga), sugarcane planthopper (Numata muiri), San Jose scale (Comstockaspis perniciosa), citrus snow scale (Unaspis citri),

[0023] Potato long-horned aphid (Aulacorthum solani), white spotted stink bug (Eysarcoris ventralis), silverleaf whitefly (Bemisia argentifolii), white leaf hopper (Cicadella spectra), white-spotted scale bug (Aspidiotus hederae), white-spotted stink bug (Liorhyssus hyalinus), white-backed psyllid (Calophya nigridorsalis), white-backed planthopper (Sogatella furcifera), broad bean long-horned aphid (Megoura crassicauda), radish aphid (Brevicoryne brassicae), soybean aphid (Aphis glycines), Taiwan spider bug (Leptocorisa oratorius), Taiwan green leafhopper (Nephotettix virescens, Taiwan long-horned aphid (Uroeucon formosanum), tobacco leaf beetle (Cyrtopeltis tennuis), tobacco whitefly (Bemisia tabaci), tea scaly scale (Lecanium persicae), black tea spotted scale (Parlatoria theae), tea leaf scale (Pseudaonidia paeoniae), tea green leafhopper (Empoasca onukii), German winged green bug (Plautia stali), tulip aphid (Dysaphis tulipae), tulip long-horned aphid (Macrosiphum euphorbiae), azalea leafhopper (Stephanitis pyrioides), horned grasshopper (Ceroplastes ceriferus), camellia black spotted scale (Parlatoria camelliae), Apolygus spinolai, Nephotettix cincticeps, Glaucia subpunctatus, Orthotylus flavosparsus, Rhopalosiphummaidis, corn planthopper (Peregrinus maidis), spiny spotted stink bug (Eysarcoris parvus), bedbug (Cimex lectularius), brown planthopper (Psylla abieti), brown planthopper (Nilaparvata lugens), Japanese pitbug (Psylla tobirae), long-legged bug (Eurydema rugosum), pear aphid (Schizaphis piricola), pear psylla (Psylla pyricola), pear spotted scale (Parlatoreopsis pyri), pear earworm (Stephanitis nashi), pear mealybug (Dysmicoccus wistariae), pear long-legged scale (Lepholeucaspis japonica), pear aphid (Sappaphis piri), false radish aphid (Lipaphis erysimi), onion aphid (Neotoxoptera formosana), husk beetle aphid (Rhopalosophum nymphaeae),

[0024] Edwardianarosae, Pinnaspisaspidistrae, Psylla alni, Speuotettix subfusculus, Alnetoidia alneti, Sogatella panicicola, Adelphocoris lineolatus, Dysdercus poecilus, Parlatoria ziziphi, Uhlerites debile, Laodelphax striatellus, Eurydema pulchrum, Cletus trigonus, Clovia punctata), leafhoppers (Empoasca sp.), Coccus hesperidum, Pachybrachius luridus, Planococcus kraunhiae, Stenotus binotatus, Arboridia apicalis, Macrosteles fascifrons, Dolycoris baccarum, Adelphocoris triannulatus, Viteus vitifolii, Acanthocoris sordidus, Leptocorisa acuta, Macropes obnubilus, Cletus punctiger, Riptortus clavatus, Paratrioza cockerelli, Aphrophora costalis, Lygus disponsi, Lygus saundersi, Crisicoccus pini, Empoasca abietis, Crisicoccus matsumotoi, Aphis craccivora, Megacopta punctatissimum, Eysarcoris guttiger, Lepidosaphes beckii,.

[0025] Diaphorina citri, Toxoptera citricidus, Planococcus citri, Dialeurodes citri, Aleurocanthus spiniferus, Pseudococcus citriculus, Zyginella citri, Pulvinaria citricola, Coccus discrepans, Pseudaonidia duplex, Pulvinaria aurantii, Lecanium corni, Nezara green stink bug viridula), wheat leafhopper (Stenodema calcaratum), wheat curl aphid (Rhopalosiphum padi), wheat long-horn aphid (Sitobion akebiae), wheat green aphid (Schizaphis graminum), wheat leafhopper (Sorhoanus tritici), wheat straw aphid (Brachycaudus helichrysi), purple stink bug (Carpocoris purpureipennis), peach aphid (Myzus persicae), peach butterbur aphid (Hyalopterus pruni), willow aphid (Aphis farinose yanagicola), willow tail bug (Metasalis populi), Yanon scale (Unaspis yanonensis), Mesohomotoma camphorae, Aphis spiraecola, Aphis pomi, Lepidosaphes ulmi, Psylla mali, Heterocordylus flavipes, Myzus aphidmalisuctus, Aphidonuguis mali, Orientus ishidai, Ovatus malicolens, Eriosoma lanigerum, Ceroplastes rubens, and Aphis gossypii.

[0026] Coleoptera pests include, for example, the Japanese longhorn beetle (Xystrocera globosa), the green leaf rove beetle (Paederus fuscipes), the green flower beetle (Eucetonia roelofsi), the azuki bean weevil (Callosobruchus chinensis), the sweet potato weevil (Cylas formicarius), the alfalfa weevil (Hypera postica), the rice weevil (Echinocnemus squameus), the rice leaf beetle (Oulema oryzae), the rice leaf beetle (Oulema oryzae), the rice leaf beetle (Donacia provosti), the rice water weevil (Lissorhoptrus oryzophilus), the potato leaf beetle (Colasposoma dauricum), the potato weevil (Euscepes postfasciatus, green beetle (Epilachna varivestis), bean weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), plum weevil (Involvulus cupreus), cucumber leaf beetle (Aulacophora femoralis), pea weevil (Bruchus pisorum), large 24-spotted ladybird (Epilachna vigintioctomaculata), turtle leaf beetle (Carpophilus dimidiatus), turtle leaf beetle (Cassida nebulosa), yellow-legged flea beetle (Luperomorpha tunebrosa), striped flea beetle (Phyllotreta striolata), yellow-spotted longhorn beetle (Psacothea hilaris), yellow spotted longhorn beetle (Aeolesthes chrysothrix, Curculio sikkimensis, Carpophilus hemipterus, Oxycetonia jucunda,

[0027] Corn rootworms (Diabrotica spp.), scarab beetles (Mimela splendens), rice weevils (Sitophilus zeamais), red flour beetles (Tribolium castaneum), rice weevils (Sitophilus oryzae), lesser red flour beetles (Palorus subdepressus), cockle beetles (Melolontha japonica), longhorn beetles (Anoplophora malasiaca), mealworms (Neatus picipes), Colorado beetles (Leptinotarsa ​​decemlineata), southern corn rootworms (Diabrotica undecimpunctata howardi), grass-lined weevils (Sphenophorus venatus), yellow long-necked beetles (Crioceris quatuordecimpunctata, plum weevil (Conotrachelus nenuphar), radish weevil (Ceuthorhynchidius albosuturalis), radish leaf beetle (Phaedon brassicae), cigarette beetle (Lasioderma serricorne), small leaf beetle (Sitona japonicus), brown scarab beetle (Adoretus tenuimaculatus), brown mealworm beetle (Tenebrio molitor), brown monkey beetle (Basilepta balyi), nail weevil (Hypera nigrirostris), tench leaf beetle (Chaetocnema concinna), cuprea beetle (Anomala cuprea), long-legged ladybird beetle (Heptophylla picea), 24-spotted ladybird beetle (Epilachna vigintioctopunctata), northern corn rootworm (Diabrotica longicornis), flower beetle (Eucetonia pilifera), wireworms (Agriotes spp.), Attagenus unicolor japonicus, Pagria signata, Anomala rufocuprea, Palorus ratzeburgii, Alphitobius laevigatus, Anthrenus verbasci, Lyctus brunneus, Tribolium confusum, Medythia nigrobilineata, Xylotrechus pyrrhoderus, Epitrix cucumeris, Tomicus piniperda, Monochamus alternatus alternatus, Japanese beetle (Popillia japonica), bean tiger beetle (Epicauta gorhami), maize weevil (Sitophilus zeamais), peach vest weevil (Rhynchites heros), vegetable weevil (Listroderes costirostris), cowpea weevil (Callosobruchus maculatus), apple weevil (Phyllobius armatus), apple blossom weevil (Anthonomus pomorum), blue leaf beetle (Linaeidea aenea), and boll weevil (Anthonomus grandis).

[0028] Dipteran (fly) pests include, for example, Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, Hydrellia sasakii, Agromyza oryzae, Hydrellia griseola, Ophiomyia phaseoli, Dacus cucurbitae, Drosophila suzukii, suzukii, Rhacochlaena japonica, Muscina stabulans, Megaselia spiracularis and other phorid flies, Clogmia albipunctata, Tipula aino, Phormia regina, Culex tritaeniorhynchus, Anopheles sinensis, Hylemya brassicae, Asphondylia sp.), seed fly (Delia platura), onion fly (Delia antiqua), European cherry fruit fly (Rhagoletis cerasi), Culex pipiens molestus Forskal, Mediterranean fruit fly (Ceratitis capitata), Siberian fungus fly (Bradysia agrestis), beet root fly (Pegomya cunicularia), tomato leafminer (Liriomyza sativae), eggplant leafminer (Liriomyza bryoniae), groundminer (Chromatomyia horticola), onion leafminer (Liriomyza chinensis), southern house mosquito (Culex quinquefasciatus), Aedes aegypti, Aedes albopictus albopictus, Liriomyza trifolii, Liriomyza sativae, Dacus dorsalis, Dacus tsuneonis, Sitodiplosis mosellana, Meromuza nigriventris, Anastrepha ludens, and Rhagoletis pomonella.

[0029] Examples of Hymenoptera (Hymenoptera) pests include Pristomyrmex pungens, ant wasps, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Dryocosmus kuriphilus, Formica fusca japonica, hornets, Athalia infumata infumata, Arge pagana, Athalia japonica, Acromyrmex spp., Solenopsis spp., Arge mali, and Ochetellus glaber.

[0030] Examples of Orthoptera (orthoptera) pests include Homorocoryphus lineosus, Gryllotalpa sp., Oxya hyla intricata, Oxya yezoensis, Locusta migratoria, Oxya japonica, Homorocoryphus jezoensis, and Teleogryllus emma.

[0031] Examples of pests of the order Thripida include Selenothrips rubrocinctus, Stenchaetothrips biformis, Haplothrips aculeatus, Ponticulothrips diospyrosi, Thrips flavus, Anaphothrips obscurus, Liothrips floridensis, Thrips simplex, Thrips nigropilosus, Heliothrips haemorrhoidalis, and Pseudodendrothrips mori), Microcephalothrips abdominalis, Leeuwenia pasanii, Litotetothrips pasaniae, Scirtothrips citri, Haplothrips chinensis, Mycterothrips glycines, Thrips setosus, Scirtothrips dorsalis, Dendrothrips minowai, Haplothrips niger, Thrips tabaci, Thrips alliorum), Thrips hawaiiensis, Haplothrips kurdjumovi, Chirothrips manicatus, Frankliniella intonsa, Thrips coloratus, Franklinella occidentalis, Thrips palmi,palmi, Frankliniella lilivora, and Liothrips vaneeckei.

[0032] Examples of pests of the order Acarina include ticks such as Leptotrombidium akamushi, Tetranychus ludeni, Dermacentor variabilis, Tetranychus truncatus, Ornithonyssus bacoti, Demodex canis, Tetranychus viennensis, Tetranychus kanzawai, and Rhipicephalus sanguineus, as well as mites such as Cheyletus malaccensis, Tyrophagus putrescentiae, Dermatophagoides farinae, and Latrodectus hasseltii, Dermacentor taiwanicus, Acaphylla theavagrans, Polyphagotarsonemus latus, Aculops lycopersici, Ornithonyssus sylvairum, Tetranychus urticae, Eriophyes chibaensis, Sarcoptes scabiei, Haemaphysalis longicornis, Ixodes scapularis, Tyrophagus similis, Cheyletus eruditus, Panonychus citri, Cheyletus moorei), Brown spider mite (Brevipalpus phoenicis), Ear mite (Octodectes cynotis), House dust mite (Dermatophagoides ptrenyssnus), Japanese mites (Haemaphysalis flava), Japanese ticks (Ixodesovatus, Ryukyu citrus rust mite (Phyllocoptruta citri), apple rust mite (Aculus schlechtendali), apple red mite (Panonychus ulmi), Lone star tick (Amblyomma americanum), as well as red mite (Dermanyssus gallinae), Robin's bulb mite (Rhyzoglyphus robini), and bulb mite (Sancassania sp.).

[0033] Examples of pests of the order Isoptera include Reticulitermes miyatakei, Incisitermes minor, Coptotermes formosanus, Hodotermopsis japonica, Reticulitermes sp., Reticulitermes flaviceps amamianus, Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus, Odontotermes formosanus, Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes speratus.

[0034] Examples of cockroach pests include the Siberian cockroach (Periplaneta fuliginosa), the German cockroach (Blattella germanica), the Oriental cockroach (Blatta orientalis), the Brown cockroach (Periplaneta brunnea), the Lesser German cockroach (Blattella lituricollis), the Japanese cockroach (Periplaneta japonica), and the American cockroach (Periplaneta americana).

[0035] Examples of nematodes include Nothotylenchus acris, Aphelenchoides besseyi, Pratylenchus penetrans, Meloidogyne hapla, Meloidogyne incognita, Globodera rostochiensis, Meloidogyne javanica, Heterodera glycines, Pratylenchus coffeae, Pratylenchus neglectus, and Tylenchus semipenetrans.

[0036] Examples of mollusks include the apple snail (Pomacea canaliculata), the African snail (Achatina fulica), the slug (Meghimatium bilineatum), the brown slug (Lehmannina valentiana), the red slug (Limax flavus), and the light blue snail (Acusta despecta sieboldiana).

[0037] The agricultural and horticultural pest control agent containing the compound represented by formula (I) or a salt thereof as an active ingredient has a remarkable control effect against pests that cause damage to paddy field crops, field crops, fruit trees, vegetables, other crops, and flowers, etc., and therefore the expected effect of the agricultural and horticultural pest control agent of the present invention can be achieved by treating the seedling facility, paddy field, field, fruit trees, vegetables, other crops, flowers, etc., paddy field water, foliage, or soil, etc., with the seedling soil of crops, flowers, etc., soil in a planting hole at the time of transplantation, the base of a plant, irrigation water, cultivation water in hydroponic cultivation, etc., with the compound of the present invention absorbed from the roots with or without the soil, utilizing the so-called systemic translocation.

[0038] Useful plants for which the agricultural and horticultural pest control agent of the present invention can be used are not particularly limited, and examples thereof include cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), beans (soybeans, adzuki beans, broad beans, peas, kidney beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leafy and fruit vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, green onion (chives, scallions), bell peppers, eggplant, strawberries, peppers, okra, Chinese chives, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, daikon radishes, turnips, lotus roots, burdock, garlic, shallots ... Examples of plants that can be used include crops for processing (cotton, hemp, beets, hops, sugar cane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), melons (pumpkin, cucumber, watermelon, Japanese gourd, melon, etc.), pasture grasses (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turf grasses (Korean grass, bentgrass, etc.), ornamental crops such as fragrances (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees (ginkgo, cherry trees, Japanese cypress, etc.), and forest trees (abarch firs, spruces, pines, Japanese cypress, cedar, cypress, eucalyptus, etc.).

[0039] The above-mentioned useful plants also include plants to which resistance to HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, acetyl-CoA carboxylase inhibitors such as sethoxydim, and herbicides such as bromoxynil, dicamba, and 2,4-D has been imparted by classical breeding methods or by genetic engineering technology.

[0040] Examples of useful plants that have been given resistance by classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone ALS inhibitor herbicides such as imazethapyr, which are already sold under the trade name Clearfield (registered trademark). Similarly, soybeans that have been resistant to sulfonylurea ALS inhibitor herbicides such as thifensulfuron methyl by classical breeding methods are already sold under the trade name STS soybeans. Similarly, examples of plants that have been given resistance to acetyl-CoA carboxylase inhibitors such as trione oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods include SR corn.

[0041] Furthermore, plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors are described in, for example, Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), vol. 87, pp. 7175-7179 (1990). In addition, mutant acetyl-CoA carboxylases resistant to acetyl-CoA carboxylase inhibitors have been reported in Weed Science, Vol. 53, pp. 728-746 (2005), and by introducing such mutant acetyl-CoA carboxylase genes into plants by genetic recombination technology or by introducing a mutation involved in imparting resistance into plant acetyl-CoA carboxylase, it is possible to produce plants resistant to acetyl-CoA carboxylase inhibitors. Furthermore, by introducing a nucleic acid with a base substitution mutation, as represented by the chimeraplasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.), into plant cells to introduce a site-specific amino acid substitution mutation into the acetyl-CoA carboxylase gene or ALS gene of a plant, it is possible to produce plants resistant to acetyl-CoA carboxylase inhibitors or ALS inhibitors, and the agricultural and horticultural pest control agent of the present invention can be used for such plants as well.

[0042] Further toxins expressed in transgenic plants include insecticidal proteins from Bacillus cereus and Bacillus popilia; δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C from Bacillus thuringiensis, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins or insect-specific neurotoxins; fungal toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors, patatins, cystatins; These include protease inhibitors such as ricin, maize-RIP, abrin, rufin, saporin, and bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; and glucanase.

[0043] Toxins expressed in such transgenic plants also include hybrid toxins, partially deleted toxins, and modified toxins of δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, or insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant technology. One example of a partially deleted toxin is Cry1Ab, which has a deleted portion of its amino acid sequence. Modified toxins have one or more amino acids substituted in the natural toxin. Examples of these toxins and recombinant plants capable of synthesizing these toxins are described in, for example, EP 0374753, WO 93 / 07278, WO 95 / 34656, EP 0427529, EP 0451878 and WO 03 / 052073.

[0044] The toxins contained in these recombinant plants confer resistance to Coleoptera, Hemiptera, Diptera, Lepidoptera, and Nematodes, among others. The agricultural and horticultural pest control agent of the present invention can be used in combination with or systematized with these techniques.

[0045] The agricultural and horticultural pest control agent of the present invention may be applied to plants where occurrence of various pests is predicted in an amount effective for pest control as it is, or in a form appropriately diluted or suspended in water, etc., in order to control various pests, and in addition to spraying on the stems and leaves for pests occurring in fruit trees, grains, vegetables, etc., it can also be applied to soil, etc. and absorbed through the roots, for example, by soaking seeds in the agent, seed dressing, seed treatment such as calper treatment, mixing in the whole soil layer, row application, mixing in bed soil, cell seedling treatment, planting hole treatment, plant base treatment, top dressing, rice box treatment, water surface application, etc. In addition, it can be applied to nutrient solution in nutrient solution (hydroponic) cultivation, smoked, or injected into tree trunks.

[0046] Furthermore, the agricultural and horticultural pest control agent of the present invention may be applied as is, or appropriately diluted or suspended in water or the like, in an amount effective for pest control in locations where occurrence of the pest is predicted. For example, it may be sprayed on grain storage pests, house pests, sanitary pests, forest pests, etc., and may also be used as a coating on building materials for houses, for smoking, as bait, etc.

[0047] Seed treatment methods include, for example, a method in which seeds are soaked in a liquid or solid formulation, either diluted or undiluted, to allow the agent to penetrate the seeds; a method in which a solid or liquid formulation is mixed with seeds and dusted to adhere to the seed surface; a method in which the formulation is mixed with an adhesive carrier such as a resin or polymer and then coated on the seeds; and a method in which the formulation is sprayed around the seeds at the same time as planting. The "seed" to be subjected to the seed treatment means a plant body in the early stage of cultivation used for plant propagation, and examples thereof include seeds, as well as bulbs, tubers, seed potatoes, sprouts, corms, bulbs, or plant bodies for vegetative propagation for cultivation by cuttings.

[0048] When carrying out the method of use of the present invention, the term "soil" or "cultivation carrier" for a plant refers to a support for cultivating crops, particularly a support for growing roots. The material is not particularly limited as long as it is a material in which plants can grow, and may be so-called soil, seedling mat, water, etc., and specific materials may be, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, polymeric substances, rock wool, glass wool, wood chips, bark, etc.

[0049] Methods for spraying on crop foliage or grain pests, house pests, sanitary pests or forest pests include a method in which a liquid formulation such as an emulsifiable concentrate or flowable concentrate, or a solid formulation such as a wettable powder or wettable granules is appropriately diluted with water and sprayed, a method in which a powder is sprayed, or fumigation. Methods for application to soil include, for example, applying a liquid formulation, with or without dilution, to the base of a plant or to a seedling bed; spraying a granule at the base of a plant or to a seedling bed; spraying a dust, wettable powder, water dispersible granule, granule, etc. and mixing it with the entire soil before sowing or transplanting; and spraying a dust, wettable powder, water dispersible granule, granule, etc. in planting holes, rows, etc. before sowing or planting plants.

[0050] For application to rice seedling boxes, the formulation may be in the form of a dust, water dispersible granule, granule, etc., depending on the application time, for example, application at the time of sowing, application during the greening period, application at the time of transplanting, etc. Application can also be by mixing with the culture soil, and the culture soil can be mixed with a dust, water dispersible granule, or granule, for example, by mixing with the bed soil, covering soil, or the entire culture soil. It may also be simply applied by layering the culture soil and various formulations alternately. For application to paddy fields, solid preparations such as jumbo, pack, granule, and granular water dispersible agent, or liquid preparations such as flowable and emulsion are usually sprayed on flooded paddy fields. In addition, at the time of rice planting, appropriate preparations can be sprayed or injected into the soil as they are or mixed with fertilizer. In addition, by using liquids such as emulsions and flowables at the water inlet and irrigation equipment, it is possible to apply them labor-savingly along with the water supply.

[0051] In field crops, the treatment can be applied to seeds or to cultivation carriers adjacent to the plant body during the sowing to seedling stage. In plants that are directly sown in the field, in addition to direct treatment to the seeds, treatment to the base of the plant during cultivation is preferred. Spraying treatment can be performed using granules, or irrigation treatment can be performed in liquid form with or without dilution in water. Another preferred treatment is to mix the granules with the cultivation carrier before sowing and then sowing. As treatments for cultivated plants to be transplanted during the sowing and seedling raising stage, in addition to direct treatment of seeds, it is preferable to irrigate liquid agents or spray granules on the seedling raising bed. It is also preferable to apply granules to the planting hole at the time of planting or to mix them with the cultivation carrier near the transplanting site.

[0052] The agricultural and horticultural pest control agent of the present invention is generally formulated into a convenient form according to the conventional method for pesticide formulation and used.That is, the compound represented by formula (I) of the present invention or its salt may be mixed in a suitable inert carrier or, if necessary, with an auxiliary in a suitable ratio, dissolved, separated, suspended, mixed, impregnated, adsorbed or attached to the compound, and used in a suitable form, such as a suspension, an emulsifiable concentrate, a liquid, a wettable powder, a wettable granule, a granule, a dust, a tablet, a pack, etc.

[0053] The agricultural and horticultural pest control agent of the present invention may contain, in addition to the active ingredient, additives that are commonly used in pesticide formulations as necessary. Examples of the additives include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, spreading agents, antifreezing agents, anticaking agents, disintegrants, and antidecomposition agents. If necessary, preservatives, plant pieces, and the like may be used as additives. These additives may be used alone or in combination of two or more.

[0054] Examples of solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride, organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose, and plant powders (e.g., sawdust, coconut shells, corn cobs, and tobacco stalks), plastic carriers such as polyethylene, polypropylene, and polyvinylidene chloride, urea, inorganic hollow bodies, plastic hollow bodies, and fumed silica (white carbon). These may be used alone or in combination of two or more.

[0055] Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin; polyhydric alcohol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; ethers such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, and tetrahydrofuran; normal paraffin, naphthenic acid, and the like; Examples of the solvent include aliphatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate, lactones such as γ-butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, and N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil, and water. These may be used alone or in combination of two or more.

[0056] Examples of surfactants used as dispersants or wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formalin condensates, polyoxyethylene polyoxypropylene block copolymers, polystyrene polyoxyethylene block polymers, alkyl polyoxyethylene polypropylene block copolymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bisphenyl ethers, polyalkylene benzyl phenyl ethers, polyoxyalkylene styryl phenyl ethers, acetylenic diols, polyoxyalkylene-added acetylenic diols, polyoxyethylene ether-type silicones, ester-type silicones, fluorine-based silicones, and the like. nonionic surfactants such as surfactants, polyoxyethylene castor oil, and polyoxyethylene hydrogenated castor oil; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, alkyl benzene sulfonates, alkyl aryl sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkyl naphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkyl naphthalene sulfonic acid, fatty acid salts, polycarboxylates, polyacrylates, N-methyl-fatty acid sarcosinates, resin salts, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkyl phenyl ether phosphates; cationic surfactants such as alkyl amine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyl trimethyl ammonium chloride, and alkyl dimethyl benzalkonium chloride;Amphoteric surfactants such as amino acid type or betaine type surfactants can be used. These surfactants can be used alone or in combination of two or more.

[0057] Examples of binders and tackifiers include carboxymethylcellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6,000 to 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipids (e.g., cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidone, copolymers of maleic acid and styrenes, (meth)acrylic acid copolymers, half esters of polymers composed of polyhydric alcohols and dicarboxylic acid anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffin, terpene, polyamide resins, polyacrylates, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, and synthetic resin emulsions.

[0058] Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, diutan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, and polysaccharides, and inorganic fine powders such as high-purity bentonite and fumed silica (white carbon).

[0059] Examples of colorants include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.

[0060] Examples of the antifreeze agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0061] Examples of adjuvants for preventing caking or promoting disintegration include polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, metal stearates, cellulose powder, dextrin, methacrylic acid ester copolymers, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers, and starch-polyacrylonitrile graft copolymers.

[0062] Examples of the decomposition inhibitor include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol compounds, amine compounds, sulfur compounds, and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.

[0063] Examples of preservatives include potassium sorbate, 1,2-benzothiazolin-3-one, etc. Furthermore, other auxiliary agents such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreeze agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers can also be used as necessary.

[0064] The blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by mass per 100 parts by mass of the agricultural and horticultural pest control agent of the present invention. For example, when used as a dust, granule, emulsion or wettable powder, 0.01 to 50 parts by mass (0.01 to 50% by mass relative to the total mass of the agricultural and horticultural pest control agent) is appropriate.

[0065] The amount of the agricultural and horticultural pest control agent of the present invention to be used will vary depending on various factors, such as the purpose, target pest, crop growth condition, pest occurrence tendency, weather, environmental conditions, formulation type, application method, application location, application time, etc., but may be appropriately selected depending on the purpose from a range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, of the active ingredient compound per 10 ares.

[0066] The agricultural and horticultural pest control agent of the present invention can be used in combination with other agricultural and horticultural insecticides, miticides, nematicides, fungicides, biological pesticides, etc. in order to expand the range of pests and diseases to be controlled and the optimal control period, or for the purpose of reducing the amount of drug used. It can also be used in combination with herbicides, plant growth regulators, fertilizers, etc. depending on the situation of use.

[0067] Other agricultural and horticultural insecticides, acaricides, and nematocides used for such purposes include, for example, 3,5-xylyl methylcarbamate (XMC), fenobucarb (BPMC), Bt toxin-based insecticides, CPCBS (chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1,3-dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, and acinonapyr. , azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanycarb, aldicarb ), aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isoamidofos, isoxathion, isocycloseram,

[0068] Isofenphos, isoprocarb (MIPC), epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin, imicyafos, imidacloprid, imiprothrin, indazapyoxamet, indoxacarb, esfenvalerate, ethiofencarb, ethion, ethiprole, etoxazole ... Fenprox, ethoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfendazole, potassium oleate oleate, sodium oleate, cadusafos, kappa-bifenthrin, cartap, carbaryl, carbosulfan, carbofuran, gamma-cyhalothrin,

[0069] xylylcarb, quinalphos, kinoprene, chinomethionat, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordimeform, chlordane (chlordane), chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, kelthane (dicofol: dicofol, salithion, cyhalodiamide, cyanophos (CYAP), diafenthiuron, diamidaphos, cyantraniliprole, theta-cypermethrin, cyetpyrafen, dienochlor, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole,

[0070] Diclofenthion (ECP), cyclobutrifluram, cycloprothrin, dichlorvos (DDVP), dichloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyphenothrin phenothrin, cyfluthrin, diflubenzuron, cyflumetofen, cyproflanilide, diflovidadin, cyhexatin, cypermethrin, dimethylvinphos, dimethoate, dimpropyridazur ridaz), dimefluthrin, silafluofen, cyromazine, spidoxamat, spinetoram, spinosad, spirodiclofen, spirotetramat, spirobudifen, spiropidione, spiromesifen romesifen, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, tioxazafen,

[0071] Thiodicarb, thiocyclam, thiosultap, thiosultap-sodium, thionazin, thiometon, thiolanthraniliprole, deet, dieldrin, tetrachlorantraniliprole, tyclopyrazoflor, tetrachlorvinphos, tetradifon, tetraniliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, Tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, doramectin, tralopyril, tralomethrin, transfluthrin, triazamate, triazuron, trichlamide, trichlorphon (DEP), trifluenfuronate, triflumezopyrium, triflumuron, tolfenpyrad, naled:BRP), nicofluprole, nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, vamidothion,

[0072] Parathion, parathion-methyl, halfenprox, halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxypropyl starch starch, binapacryl, pyflubumide, bifenazate, bifenthrin, pymetrozine, pyraclorfos, pyrafluprole, pyridaphenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins, fipronil iproni1), fenazaquin, fenamiphos, phenisobromorate, fenitrothion (MEP), fenoxycarb, fenothiocarb, fenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoate (PAP), fenvalerate, fenpyroximate, fenpropathrin, fenbendazole, phenmezoditiaz, fosthiazate,Formetanate, butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim, furazaindolizine, fluazinam, fluazuron, fluensulfone, fluxametamide,

[0073] Fluchlordiniliprole, flucycloxuron, flucythrinate, fluvalinate, flupyradifurone, flufiprole, flupyradifurone, flupyrazofos, flupyrimin, flupyroxystrobin, flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenprox, fluproxyfen, flubrocythrinate rinate, fluhexafon, flubendiamide, flupentiofenox, flumethrin, flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite (BPPS), profenofos, broflanilide, profluthrin, propoxur (PHC), flometoquin, alpha-bromadiolone, bromopropylate, beta-cyfluthrin,

[0074] Hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiaz, bendiocarb, benzpyrimoxan, bensultap, benzoximate, benfuracarb uracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (PMP), polynactins, formetanate, formothion, phorate, machine oil oil), malathion, milbemycin, milbemycin A, milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam-sodium, methiocarb,

[0075] Methidathion (DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, metoxadiazone, methoxychlor, methoxyfenozide, metofluthrin, methoprene, metolcarb, meperflusuri meperfluthrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin, ryanodine, lufenuron, rescalure, resmethrin, lepimectin, rotenone, levamisole hydrochloride Examples of suitable antihistamines include nicotine, nicotine sulfate, nicotine sulfate-1, nicotine sulfate-2, nicotine sulfate-3, nicotine sulfate-4, nicotine sulfate-5, nicotine sulfate-6, nicotine sulfate-7, nicotine sulfate-8, nicotine sulfate-9, nicotine sulfate-10, nicotine sulfate-11, nicotine sulfate-12, nicotine sulfate-13, nicotine sulfate-14, nicotine sulfate-15, nicotine sulfate-16, nicotine sulfate-17, nicotine sulfate-18, nicotine sulfate-19, nicotine sulfate-20, nicotine sulfate-21, nicotine sulfate-22, nicotine sulfate-23, nicotine sulfate-24, nicotine sulfate-25, nicotine sulfate-31, nicotine sulfate-32, nicotine sulfate-33, nicotine sulfate-34, nicotine sulfate-35, nicotine sulfate-36, nicotine sulfate-37, nicotine sulfate-38, nicotine sulfate-39, nicotine sulfate-39, nicotine sulfate-41, nicotine sulfate-51, nicotine sulfate-52, nicotine sulfate-53, nicotine sulfate-54, nicotine sulfate-5 ...

[0076] Examples of compounds (fungicides) having fungicidal activity include aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, aminopyrifen, ampropylfos, ametoctradin, and allyl alcohol. alcohol), aldimorph, amobam, isotianil, isovaledione, isopyrazam, isofetamide, isoflutipram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam,

[0077] iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, inpyrfluxam, uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole, ethaboxam, ethirimol, etem, ethoxyquin, etridiazole iazole, enestroburin, enoxastrobin, epoxiconazole, oxadixyl, oxathiapiprolin, oxycarboxin, copper-8-quinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate, oxolinic acid acid), octhilinone, ofurace, orysastrobin, metam-sodium, kasugamycin, carbamorph, carpropamid, carbendazim,

[0078] Carboxin, carvone, quinazamid, quinacetol, quinoxyfen, quinofumelin, chinomethionat, quinomethionate, captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine tine), cufraneb, cuprobam, coumoxystrobin, glyodin, griseofulvin, climbazole, cresol, kresoxim-methyl, chlozolinate, clotrimazole, chlobenthiazone, chloraniformethan,

[0079] Chloranil, chlorquinox, chloropicrin, chlorphenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, chloroneb, salicylanilide, zarilamid, cyazofamid, diethyl pyropate carbonate pyrocarbonate), diethofencarb, cyclafuramid, diclocymet, dichlozoline, diclobutrazol, dichlofluanid, cycloheximide, dichlobentiazox, diclomezine,

[0080] Dicloran, dichlorophen, dichlon, disulfiram, ditalimfos, dithianon, diniconazole, diniconazole-M, zineb, dinocap, dinocton, dinosulfon, dinoterbone, dinobuton, dinopenton, dipymetitrone, dipyrithione, diphenylamine, difenoconazole, Flufenamid, diflumetorim, cyproconazole, cyprodinil, cyprofuram, cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, seboctylamine,

[0081] Zoxamide, dazomet, thiadiazin, tiadinil, thiadifluor, thiabendazole, tioxymid, thioquinox, thiochlorfenphim, thiophanate, thiophanate-methyl, thifluzamide, thicyofen, thioquinox, thiram, decaphentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid acid), tebuconazole, tebufloquin, dodicin, dodine, dodecylbenzenesulfonic acid bisethylenediamine copper complex salt (II) (DBEDC), dodemorph,

[0082] Drazoxolon, triadimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol, trichlamide, triclopyricarb, tricyclazole, triticonazole, tridemorph, tributyltin oxide oxide), triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb, natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin, valifenalate, harpin proteinprotein), picarbutrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroxyisoxazole potassium, binapacryl, biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarbolid,

[0083] pyraclostrobin, pyraziflumid, pyrazophos, pyrapropoyne, pyrametostrobin, pyriophenone, pyridinitril, pyrifenox, pyridiflumetofen, pyrisoxazole, pyridaclomethyl, pyrifenox, pyribencarb, pyriminostrobin, pyrimethanil, pyroxychlor, pyroxyfur, pyroquilon, vinclozolin ozolin), ferbam, famoxadone, fenapanil, fenamidone, fenaminosulf, phenaminestrobin, fenarimol, fenitropan, fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpicoxamid, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid,

[0084] Phthalide, buthiobate, butylamine, bupirimate, fuberidazole, blasticidin-S, furametpyr, furalaxyl, fluacrypyrim, fluazinam, fluindapyr, fluoxastrobin, fluoxapiprolin, fluoxytioconazole, fluotrimazole trimazole), fluopicolide, fluopimomide, fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinconazole, fluconazole, fluconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil,

[0085] Flutriafol, flufenoxadiazam, flufenoxystrobin, furfural, flubeneteram, furmecyclox, flumetylsulforim, flumetover, flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole, pronitridine, propamocarb amocarb), propiconazole, propineb, furophanate, probenazole, bromuconazole, florylpicoxamid, hexachlorobutadiene, hexaconazole, hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox,

[0086] penconazole, benzamorf, pencycuron, benzohydroxamic acid, benzovindiflupyr, bentaluron, benthiazole, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl-aluminum, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil oil), maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, methasulfocarb, metazoxolone, metam, metam-sodium, metalaxyl,

[0087] Metalaxyl-M, metarylpicoxamid, metiram, methyl isothiocyanate isothiocyanate, methyl dinocap, methyl tetraprole, metconazole, metsulfovax, metfuroxam, metominostrobin, metrafenone, mepanipyrim, mefenoxam, mefentrifluconazole, meptyl dinocap, mepronil, mebenil, methyl iodide, rabenzazole, methyl bromide,

[0088] Examples of suitable germicides include inorganic germicides such as benzalkonium chloride, basic copper chloride, basic copper sulfate, and metallic silver; sodium hypochlorite, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, inorganic sulfur; copper-based compounds such as copper sulfate anhydride, nickel dimethyldithiocarbamate, and 8-hydroxyquinoline copper; zinc sulfate; and copper sulfate pentahydrate, or salts thereof.

[0089] Compounds (herbicides) with herbicidal activity include 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, asulam, acetochlor, atrazine, atraton,

[0090] Anisuron, anilofos, aviglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amivudine, amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor r), alloxydim, arorac, iofensulfuron, isouron, isocarbamide, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, isocyl, isonoruron, isoproturon,

[0091] Isopropalin, isopolinate, isomethiozin, inabenfide, ipazine, iptriazopyrid, ipfencarbazone, iprimidam, imazaquin, imazapic, imazapyr zapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutyric acid, uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron-methyl, ethalfluralin, ethiolate, ethychlozate-ethyl,

[0092] Ethidimuron, ethinofen, ethephon, ethoxysulfuron, ethoxyfen, etnipromid, ethofumesate, etobenzanid, epirifenacil, epronaz, erbon, endothal, oxadiazon, oxadiargyl adiargyl, oxaziclomefone, oxasulfuron, oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, cafenstrole, cambendichlor, carbasulam, carfentrazone,

[0093] carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop, quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron, clacyfos, clioginate (cliodinate), glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop, clodinafop-propargyl, clotoluron, clopyralid, cloproxydim, cloprop, clobromuron, clofop,

[0094] clomazone, chlomethoxynil, chlomethoxyfen, clomeprop, chlorazifop, chlorazine, chlorasulam, chloranocryl, chloramben, cloransulam, cloransulam-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlor chlortoluron, chlornitrofen, chlorfenac, chlorfenprop, chlorbufam, chlorphthalim, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil, chloroxuron, chlorotoluron, chloropon, cypyrafluone,

[0095] Saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat, dioxopyritrione, dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlorprop, dichlorprop-P, dichlobenil, dichlobenz-methyl, diclofop, diclofop-methyl, dichlormate, dichloralurea ( dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop , cyhalofop-butyl, diphenamid, difenoxuron, difenopenten, difenzoquat, cybutryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn,

[0096] Cypromid, cyperquat, gibberellin, simazine, dimexano, dimesulfazet, dimethachlor, dimidazon, dimethametryn, dimethenamid, simetryn, simeton, dimepiperate, dimefuron, cinmeth ylin), swep, sulglycapin, sulcotrione, sulfalate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton, sethoxydim, sebuthylazine, terbacil, daimuron,

[0097] Dazomet, dalapon, thiazafluron, thiazopyr, thiaphenacyl, thiencarbazone, thiencarbazone-methyl, thiocarbazil, thioclorim, thiobencarb, thidiazimin, thidiazuron thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet, tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton , tepraloxydim, tefuryltrione, tembotrione, delaclor, terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, triaziflame iaziflam, triasulfuron, triafamone, tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron, tripyrasulfone, trifludimoxazin,

[0098] Triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron, tribenuron-methyl, triphop, trifopsime, trimeturon, tolpyralate, naptalam, naproanilide, naproamide, nicosulfuron, nitralin, nitrofen, nitrofluorfen fluorfen, nipyraclofen, neburon, norflurazon, noruron, barban, paclobutrazol, paraquat, parafluron, haloxydine, haloxifene, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosaphene, halosulfuron, halosulfuron-methyl, bialafos, bixlozone, picloram,

[0099] Picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, pydanon, pinoxaden, bipyrazone, bifenox, piperophos, hymexazol, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron, pyrazosulfuron-ethyl -ethyl), pyrazolate, bilanafos, pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyriflubenzoxim, pyribenzoxim, pyrimisulfan, pyrimisulfuron,

[0100] pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, phenothiol, fenoprop, fenobenzuron ( phenobenzuron, fenquinotrione, fenthiaprop, fenteracol, fentrazamide, phenmedipham, phenmedipham-ethyl, fenpyrazone, butachlor, butafenacil, butamifos, buthiuron, buthidazole,

[0101] butyrate, buturon, butenachlor, butoxydim, butralin, butroxydim, flazasulfuron, flamprop, furyloxyfen, prinachlor, primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop-butyl, fluazolate, fluchloraminopry, fluchlora minopir-tefuryl, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium, fluchloralin, flusulfinam, flucetosulfuron,

[0102] Fluthiacet, fluthiacet-methyl, flupyrsulfuron, flufenacet, flufenican, flufenoximacil, flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac pentyl orac-pentyl, flumipropyn, flumezin, fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proglinazin, procyazine, prodiamine, prosulfalin, prosulfuron,

[0103] Prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin, prohexadione-calcium, propoxycarbazone, propoxycarbazone-sodium, profoxydim, bromacil ), brompyrazone, prometryn, prometon, bromoxynil, bromofenoxim, bromobutide, bromobonil, florasulam, florpyrauxifen, hexachloroacetone, hexazinone, petoxamid, benazolin, penoxsulam, pebulate, beflubutamid, beflubutamid-M, vernolate, perfluidone,

[0104] Bencarbazone, benquitrione, benzadox, benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine,

[0105] Fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazide, mecoprop, mecoprop-P, medinoterb, mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprazine, mesoprotryne, metazachlor, methazole, metazosulfuron, methabenzthiazuron, metamitron, metamifop, metham, methalpropa lin), methiuron, methiozolin, methiobencarb, methyldymron, metoxuron, metoslam, metsulfuron, metsulfuron-methyl, metflurazon, metobromuron, metobenzuron, metometon, metolachlor, metribuzin, mepiquat-chloride, mefenacet,

[0106] Mefluidide, monalide, monisouron, monuron, monochloroacetic acid, monolinuron, molinate, morphamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, lancotrione, rimisoxafen, linuron, rimsulfuron, lenacil, rhodethanil, calcium peroxide, methyl bromide bromide, or a salt thereof.

[0107] Examples of biological pesticides include Agrobacterium radiobacter (e.g., "Galltrol-A" manufactured by AgBioChem, CA using strain K84, and "Nogall" manufactured by Becker Underwood, US using strain K1026), Agrobacterium radiobacter (e.g., "Bacteroses" manufactured by Nippon Nohyaku Co., Ltd. using strain 84), Ampelomyces quisqualis (e.g., "AQ10" manufactured by IntrachemBio Italia & Co. KG using strain AQ10), Aspergillus flavus (e.g., "Afla-Guard" manufactured by Syngenta, and "Arizona Cotton Research and Protection AF36® from Council, US, Afla-Guard from Syngenta using NRRL 21882), Aureobasidium pullulans (e.g. Botector® from bio-ferm, GmbH, which is a mixture of blastospores of strain DSM 14940 and blastospores of strain DSM 14941),

[0108] Bacillus amyloliquefaciens (e.g. Impression Clear® from Idemitsu Agri Co., Ltd. using the strain AT-332, and Avogreen® from University of Pretoria using the strain B246), strain D747 (e.g. Bacstar® from Etec Crop Solutions, NZ, Shelter® from Dagutat Biolab, ZA using the strain DB101, Artemis® from Dagutat Bio lab, ZA using the strain DB102, RhizoVital® from ABiTEP, DE using the strain FZB42, Kodiak® from Bayer Crop Science AG, DE using the strain GB03, Becker® from Bayer Crop Science AG, DE using the strain MBI600, Subtilex® from Underwood, US, Amplitude from Marrone Bio Innovations, Inc. using strain F727), Bacillus cepacia (e.g., Deny Stine® from Microbial Products), Bacillus cereus (e.g., Mepichlor® from Arysta, US using strain BP01), Bacillus firmus (e.g., BioNeem® from AgoGreen using strain I-1582),

[0109] Bacillus lacticola (e.g., from Micro Flo Company), Bacillus lactimorbus (e.g., from Micro Flo Company), Bacillus lactis (e.g., from Micro Flo Company), Bacillus laterosporus (e.g., Bio-Tode® from Agro-Organics, SA), Bacillus licheniformis (e.g., EcoGuard Biofungicide® from Novozymes using strain SB3086), Bacillus maroccanus (e.g., from Micro Flo Company), Bacillus megaterium (e.g., Bio Fungicide® from Novozymes using strain YFM3.25), Bacillus lacticola (e.g., from Micro Flo Company), Bacillus lactimorbus (e.g., from Micro Flo Company), Bacillus lactis ... "Bioarc®" from "Arc"), Bacillus metiens (e.g., from "Micro Flo Company"), Bacillus mojavensis (e.g., from "Probelte,Sa" using strain SR11), Bacillus mycoides (e.g., "BmJ®" from "Certis USA" using isolate J.),

[0110] Bacillus nigrificans (e.g., manufactured by Micro Flo Company), Bacillus popilliae (e.g., Cronox® manufactured by Bio Crop, CO), Bacillus pumilus (e.g., Integral F-33® manufactured by Becker Underwood, US using strain BUF-33, Yield Shield® manufactured by Bayer Crop Science AG, DE using strain GB34, Sonata® manufactured by Bayer CropScience LP, US using strain QST2808), Bacillus simplex (e.g., Momihope® manufactured by Arista Life Sciences, Inc. using strain CGF2856), Bacillus sphaericus sphaericus (e.g., "VectoLex®" from Valent BioSciences, US, using serotype H5a5b strain 2362);

[0111] Bacillus subtilis (e.g., Botkiller hydrate (registered trademark) manufactured by Idemitsu Agri Co., Ltd., Taegro (registered trademark) manufactured by Novozyme Biologicals, Inc. US using the strain FZB24, SERENADE (registered trademark) manufactured by Bayer CropScience LP, US using the strain QST713 / AQ713) MAX®, Serenade-DPZ® using strain AQ30002, Ecoshot® from Kumiai Chemical Co., Ltd. using strain D747, Agrocare® from Nisso Green Co., Ltd. using strain HAI-0404, Botopica® from Idemitsu Kosan Co., Ltd. using strain MBI600, Batistar® from Arista Life Sciences Co., Ltd. using strain Y1336, Companion Biological Fungicide Wettable Powder from Growth Products Ltd using strain GB03), Bacillus thuringiensis (e.g. VectoBac® from Valent BioSciences, US using strain AM65-52), Bacillus thuringiensis aizawai aizawai) (e.g., "XenTari®" manufactured by "Bayer Crop Science AG, DE" using strain ABTS-1857, "Florbac WG®" manufactured by "Valent BioSciences, US" using serotype H-7, and "Agree WG Biological Insecticide" manufactured by "Certis USA" using strain GC-91), Bacillus thuringiensis aegypti (Bacillus thuringiensis subspecies.Aegypti (e.g., Agerin®), Bacillus thuringienses israelensis (e.g., Aquabac® from Becker Microbial Products IL using strain BMP144),

[0112] Bacillus thuringienses kurstaki (e.g., Dipel ES® from Becker Microbial Products, IL using strain BMP 123, Dipel ES® from Valent BioSciences, US using strain HD-1, BMP 123 from Becker Microbial Products using strain BMP123, BMP144 / Aquabac from Becker Microbial Products using strain BMP144, Dipel 10G from Valent USA LLC. using strain ABTS-351, Condor Wettable Powder from Certis USA using strain EG2348, Crymax Bioinsecticide from Certis USA using strain EG7841, Deliver Biological Insecticide from Certis USA using strain SA-12, AEF Insecticide from Certis USA using strain EVB-113-19, Global) (e.g., Bioprotec PLUS), Bacillus thuringiensis galleriae (e.g., beetleGONE! from Phyllom BioProducts and boreGONE! from Phyllom BioProducts using strain SDS-502),

[0113] Examples of suitable strains include Bacillus thuringiensis var. Colmeri (e.g. TianBaoBTc® from Changzhou Jianghai Chemical Factory), Bacillus thuringienses tenebrionis (e.g. Novodor FC® from BioFa DE using the strain NB176), Bacillus thuringiensis var. san diego (e.g. M-One® from Bacillus thuringiensis var. san diego), Beauveria bassiana (e.g. Naturalis® from Intrachem Bio Italia and Bove® from Novozymes using the strain CG716), Bacillus thuringiensis var. san diego (e.g. Naturalis® from Intrachem Bio Italia and Bove® from Novozymes using the strain CG716), Bacillus thuringiensis var. san diego (e.g. M-One® from Bacillus thuringiensis var. san diego ... M-One® from Bacillus thuringiensis var. san diego), Bacillus thuringiensis var. san diego (e.g. M-One® from "Max (registered trademark)" manufactured by "Idemitsu Kosan Co., Ltd." using strain F-263, "Biolisa Madara (registered trademark)" manufactured by "ARYSTA" using strain GHA, "balEnce" manufactured by "Terragena, Inc." using strain HF23, "BotaniGard ES" manufactured by "BioWorks Inc." using strain GHA, "BioCeres WP" manufactured by "BioSafe Systems" using strain ANT-03),

[0114] Beauveria brongniartii (e.g. Beaupro® from Andermatt Biocontrol AG), Bradyrhizobium japonicum (e.g. Optimize® from Novozymes), Burkholderia spp. (e.g. MBI-206 TGAI® from Marrone Bio Innovations using strain A396), Candida oleophila (e.g. Aspire® from Ecogen Inc., US using strain I-82 and Nexy® from BioNext using strain O), Candida saitoana (e.g. Micro Flo Company, US (BASF BIOCURE® from AgriLife), Chaetomium cupreum (e.g. BIOKUPRUM™ from AgriLife), Chaetomium globosum (e.g. Rivadiom® from Rivale), Chromobacterium subtsugae (e.g. Grandevo® from Marrone Bio Innovations using strain PRAA4-1T),

[0115] Cladosporium cladosporioides (e.g., from Cladosporium cladosporioides), Clonostachys rosea f. catenulate (e.g., from Verdera, Finland in PRESTOP® using strain J1446), Colletotrichum gloeosporioides (e.g., from Agriultural Research Initiatives in Collego®), Coniothyrium minitans (e.g., from Encore Technologies, LLC in Contans® using strain CON / M / 91-08), Cryptococcus albidus (e.g., from Anchor Bio Technologies, ZA), Delftia acidovorans (e.g. BioBoost® from Brett Young Seeds using strain RAY209), Dilophosphora alopecuri (e.g. Twist Fungus®), Drechsrela monoceras (e.g. Tasmart Herbicide® from Mitsui Chemicals Agro using strain MTB-951), Entomophthora virulenta (e.g. Vektor® from Ecomic), Fusarium oxysporum oxysporum (e.g., "Marcalite" manufactured by Eisai Seikakensha using strain 101-2), Fusarium oxysporum (e.g., "Fusaclean" manufactured by Natural Plant Protection using strain Fo47),

[0116] Gliocladium spp. (e.g., Prestop® from AgBio Inc. using strain J1446 and from WF Stoneman Company LLC using strain 321U), Hirsutella thompsonii (e.g., Mycohit® from Agro Bio tech Research Centre, IN), Lactobacillus acidophilus (e.g., Fruitsan® from Inagrosa Industrias Agrobiologicas, SA), Lactobacillus plantarum (e.g., Lactoguard Wettable Powder from Meiji Seika Pharma Co., Ltd. using strain BY), Lecanicillium lecanii lecanii (e.g., Mycotal® from Koppert / Arysta using conidia of strain KV01), Metarhizium anisopliae (e.g., BIO 1020® from Bayer CropScience using strain F52, Pirate Granules® from Arysta LifeSciences using strain SMZ-2000, Bio-Blast from LidoChem Inc using strain ESC1),

[0117] Metarhizium anisopliae var. acridum (e.g. Green Muscle® from Biological Control Products and GreenGuard® from Becker Underwood, US), Metschnikowia fructicola (e.g. Shemer® from Bayer CropScience), Microdochium dimerum (e.g. ANTIBOT® from Agrauxine, France), Microsphaeropsis ochracea (e.g. Microx® from Prophyta), Monacrosporium phymatopagum (e.g. Phytophthora spp.), phymatopagum (e.g., Nemahiton® from Tomoe Chemical Industry Co., Ltd.), Mucor haemelis (e.g., BioAvard® from Indore Biotech Inputs & Research), Muscodor albus (e.g., Arabesque from Bayer Crop Science using strain QST 20799), Myrothecium verrucaria (e.g., DiTera™ from Valent Biosciences using strain AARC-0255), Paecilomyces fumosoroseus (e.g., strain apopka "PreFeRal (registered trademark) WG" manufactured by "Biobest" using 97, "Preferred wettable powder" manufactured by "Tokai Bussan Co., Ltd.", "Natural Industries Inc.(No Fly® from Novozymes company), Paecilomyces lilacinus (e.g. BioAct WG® from Prophyta using strain 251),

[0118] Paecilomyces tenuipes (e.g., Gotz A® from Idemitsu Kosan Co., Ltd. using strain T1), Paecilomyces variotii (e.g., Nemaquim® from Quimia,MX using strain Q-09), Paenibacillus polymyxa (e.g., Topseed® from Green Biotech Company Ltd. using strain AC-1), Paenibacillus poppiliae (e.g., Milky spore disease® from St. Gabriel Laboratories), Pasteuria nishizawae (e.g., Pasteuria "oyacystLF / ST (registered trademark)" from "Pasteuria Bioscience" and "Clariva pn" from "Syngenta" using strain Pn1), Pasteuria penetrans (e.g. "Pasteuria (registered trademark)" from "Pasteuria Bioscience"), Pasteuria usagae (e.g. "Econem (registered trademark)" from "Pasteuria Bioscience"),

[0119] Pantoea agglomerans (e.g., Bloomtime Biological FD Biopesticide from Nufarm US using strain E325), Pectobacterium carotovorum (e.g., Biokeeper from Nissan Chemical Co., Ltd. and Ecomate from Kumiai Chemical Co., Ltd. using strain CGE234M403), Phoma macrostroma (e.g., Phoma H from Scotts, US using strain 94-44B), Penicillium bilaii (e.g., Jump Start from Novozymes), Phlebiopsis gigantea (e.g., FOC PG ... "ROTSOP®" from "Verdera, Finland" using B22 / SP1190 / 3.2), Pochonia chlamydosporia var.catenulata (e.g., KlamiC® from The National Center of Animal and Plant Health (CENSA); CU), Pseudomonas aureofaciens (e.g., Spot-Less Biofungicide® from Eco Soils Systems, CA using strain TX-1), Pseudomonas chlororaphis (e.g., ATEze® from EcoSoil Systems using strain 63-28 and Cedomon® from Bioagri, S using strain MA342), Pseudomonas fluorescens (e.g., Frostban® from Frost Technology Corp using strain 1629RS), D (registered trademark), Blightban (registered trademark) manufactured by Blightban using strain A506, Konae Fukudo (registered trademark) manufactured by Taki Chemical Co., Ltd. using strain FPT-9601, Cellnae Genki (registered trademark) manufactured by Taki Chemical Co., Ltd., which is a mixture of strains FPT-9601 and FPH-9601, VegiKeeper (registered trademark) manufactured by Arysta Life Sciences Co., Ltd. using strain G7090), Pseudomonas proradix (e.g., [Proradix (registered trademark)] manufactured by Sourcon Padena), etc.

[0120] Pseudomonas resinovorans (e.g., Solanacure® from Agricultural Research Council, SA), Pseudomonas syringae (e.g., Biosave® from EcoScience, US using strain MA-4, Frostban C from Frost Technology Corp® using strain 742RS, Bio-save 10LP Biological Fungicide from Jet Harvest Systems using strain ESC10, and Bio-Save 11 LP Biological Fungicide from Jet Harvest Systems using strain ESC11), Pseudomonas spp. spp. (e.g., "Masterpiece hydrate" manufactured by Nippon Soda Co., Ltd. using the strain HAI-0804, and "Momigenki hydrate" manufactured by Nissan Chemical Industries, Ltd. using the strain CAB-02), Pseudozyma aphidis (e.g., manufactured by Yissum Research Development Company of the Hebrew University of Jerusalem), Pseudozyma flocculosa (e.g., "Sporodex L" manufactured by Plant Products Co. Ltd, CA using the strain PF-A22 UL), Pythium oligandrum (e.g., "Polyversum" manufactured by Bioprepraty, CZ using the strain DV74 or M1), Reynoutria sacrinensis (e.g., "Pythium sacrinensis" manufactured by Bioprepraty, CZ using the strain DV74 or M1), sachlinensis) (e.g., "REGALIA (registered trademark)" manufactured by Marrone BioInnovations, US),

[0121] Examples of suitable microbial strains include Rhizopogon amylopogon (e.g., Myco-Sol® from Helena Chemical Company), Rhizopogon fulvigleba (e.g., Myco-Sol® from Helena Chemical Company), Saccharomyces cerevisiae (e.g., Lesaffre et Compagnie, FR), Sclerotinia minor (e.g., Sarritor® from Agrium Advanced Technologies), Serratia entomophila (e.g., Invade® from Wrightson Seeds), Sporothrix insectorum (e.g., Sporothrix Es (registered trademark)), Steinernema carpocapsae (e.g., Biosafe (registered trademark) from SDS Biotech Co., Ltd.), Steinernema kushidai (e.g., Shibaichinema from Kubota Co., Ltd.), Steinernema glaseri (e.g., Biotopia (registered trademark) from Arista Life Sciences Co., Ltd.), Streptomyces acidiscabies (e.g., MBI-005EP (registered trademark) from Marrone Bioinnovations, CA using strain RL-110T), Streptomyces candidus (e.g., BioBac (registered trademark) from Biontech, TW using strain Y21007-2),

[0122] Streptomyces galbus (e.g., Mycostop® from Verdera, strain K61), Streptomyces lydicus (e.g., ACTINOVATE® from Natural Industries, US, using strain WYEC108), Streptomyces saraceticus (e.g., Clanda® from A&A Group (Agro Chemical Corp.)), Talaromyces flavus (e.g., FirKeeper® from Central Glass Co., Ltd., using strain B-422, TuffBlock® from Idemitsu Kosan Co., Ltd., using strain SAY-Y-94-01, PROTUS® from Prophyta, DE, using strain V117b, WG), Trichoderma asperellum (e.g., strain ICC 012 from Isagro, strain T34 from Bioncontrol Technologies, ES, strain T34 from ECO-HOPE from Kumiai Chemical Industry Co., Ltd., strain SKT-1), Trichoderma atroviride (e.g., Esquive WP from Agrauxine, FR, Tenet or SENTINEL from Agrimm Technologies Ltd, NZ, strain LC52 from EcoHOPE DJ from Kumiai Chemical Industry Co., Ltd., strain SKT-1), Trichoderma gamsii (e.g., Bayer "BIO-TAM™ (registered trademark)" manufactured by "CropScience LP, US"

[0123] Trichoderma harzianum (e.g., T-Gro 7456® from Dagutat Biolab using strain DB103, Trianum-P® from Koppert using strain ITEM908, Trichoplus® from Biological Control Products, SA using strain KD, ROOT PRO® from Mycontrol Ltd. using strain TH-35), Trichoderma harzianum rifai (e.g., PLANTSHIELD T-22G® from Firma BioWorks Inc. US using strain T-22 and TRICHODEX® from Makhteshim Ltd, US using strain T-39), Trichoderma lignorm lignorum (e.g., Mycotric® from Futureco Bioscience, ES using strain TL-0601), Trichoderma polysporum (e.g., Binab TF WP® from BINAB Bio-Innovation AB, Sweden), Trichoderma stromaticum (e.g., TRICOVAB® from Ceplac; Brazil), Trichoderma virens (e.g., SOILGARD® from Certis LLC, US using strain GL-21),

[0124] Trichoderma viride (e.g. REMEDIER® WP from Isagro Ricerca, ITALIA using strain ICC080 and Trianum-P® from Koppert using strain TV1), Tsukamurella paurometabola (e.g. HeberNem® using strain C-924), Ulocladium oudemansii (e.g. Botry-Zen® from Botry-Zen Ltd, NZ using strain HRU3 and BotryStop from BioWorks Inc. using strain U3), Variovorax paradoxus paradoxus (e.g., Field Keeper hydrated powder (registered trademark) manufactured by Central Glass using the strain CGF4526), ​​VA (Vesicular-Arbuscular Mycorrhiza) mycorrhizal fungi (e.g., Dr. Kinkon (registered trademark) manufactured by Idemitsu Agri), Verticillium alboatrum (e.g., Dutch Trig (registered trademark) manufactured by Tree Care Innovations using the strain WCS850), Verticillium lecanii (e.g., Vertalec (registered trademark) manufactured by Arysta Life Sciences using the strain IMI 179172 and Mycotar (registered trademark) manufactured by Arysta Life Sciences using the strain IMI 263817), Xanthomonas campestris (e.g., 1,2-dichlorophenyl 2,4 ... campestris) (for example, "Camperico Liquid (registered trademark)" manufactured by "Taki Chemical Co., Ltd."), Xanthomonas campestris pv.poae, Heterorhabditis bacteriophora, Steinernema feltiae, Steinernema kraussei, Steinernema riobrave, Steinernema scapterisci, or mutants of these strains having all of the identifying characteristics of the respective strains, or metabolites produced by the respective strains that exhibit activity against plant pathogenic fungi. EXAMPLES

[0125] As representative examples of the present invention, production examples, formulation examples and test examples are shown below, but the present invention is not limited to these. A production example is shown below.

[0126] Manufacturing Example Preparation of (S)-N-(1-(1-(6-trifluoromethylpyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide (the compound of the present invention) [ka] 400 mg (1.22 mmol) of (S)-N-(2-amino-1-methyl-2-oxoethyl)-3,5-bis(trifluoromethyl)benzamide was suspended in 10 mL of chloroform, 218 mg (1.82 mmol) of N,N-dimethylformamide dimethyl acetal was added, and the mixture was heated and stirred at 50°C for 1 hour. The solvent was distilled off from the reaction solution under reduced pressure to obtain a crude compound represented by formula (IV). 4 mL of dioxane and 4 mL of acetic acid were added to the crude compound represented by formula (IV) obtained and homogenized, and then 239 mg (1.34 mmol) of 4-hydrazino-6-(trifluoromethyl)pyrimidine was added in three portions at room temperature while stirring. The reaction solution was stirred at 50°C for 10 hours, and the solvent was distilled off under reduced pressure. 30 mL of ethyl acetate was added to the residue, washed with 10 mL of saturated sodium bicarbonate water, and the ethyl acetate layer was dried over magnesium sulfate. After filtering the drying agent, the solvent was distilled off from the filtrate under reduced pressure. 5mL of n-hexane / ethyl acetate mixed solvent (volume ratio 4 / 1) was added to the residue, and the precipitated crystals were filtered and washed with 5mL of n-hexane to obtain 516mg of the present compound (S)-N-(1-(1-(6-trifluoromethylpyrimidin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide. Yield: 85% Physical properties: Melting point 162~164℃

[0127] Reference manufacturing example Preparation of 4-hydrazino-6-(trifluoromethyl)pyrimidine The 4-hydrazino-6-(trifluoromethyl)pyrimidine used in the above Production Example 1 is a known compound, but was produced as follows. [ka] 3.29g (65.7mmol) of hydrazine hydrate was added to 10mL of ethanol with stirring, and the mixture was cooled to 0℃ in an ice bath. 4.00g (21.9mmol) of 4-chloro-6-(trifluoromethyl)pyrimidine was slowly added dropwise with stirring. After the addition was completed, the mixture was stirred at room temperature for 12 hours, and half of the ethanol was distilled off under reduced pressure. The precipitated solid was filtered and washed with 5mL of cold water and 5mL of cold ethanol in that order, to obtain 2.18g (yield 56%) of the desired 4-hydrazino-6-(trifluoromethyl)pyrimidine.

[0128] Formulation examples of agricultural and horticultural pest control agents are shown below. In the formulation examples, parts indicate parts by weight. Formulation example 1. Compound of the present invention 10 parts Xylene 70 parts N-Methylpyrrolidone 10 parts Polyoxyethylene nonylphenyl ether Mixed with calcium alkylbenzene sulfonate 10 parts The above ingredients are mixed and dissolved uniformly to prepare an emulsion.

[0129] Formulation example 2. Compound of the present invention Part 3 82 parts clay powder 15 parts diatomaceous earth powder The above ingredients are mixed and ground uniformly to obtain a powder.

[0130] Formulation example 3. Compound of the present invention 5 parts 90 parts of bentonite and clay powder mixture Calcium lignosulfonate 5 parts The above ingredients are mixed uniformly, an appropriate amount of water is added, the mixture is kneaded, granulated, and dried to give granules.

[0131] Formulation example 4. Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether Mixed with calcium alkylbenzene sulfonate 5 parts The above ingredients are mixed uniformly and pulverized to prepare a wettable powder.

[0132] Test examples are shown below. As a comparative compound, (S)-N-(1-(1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide was used. This compound is described as No. 66 in Patent Document 1 and as No. I-66 in Patent Document 2, and is represented by the following structural formula. [ka] Test example 1. Control value test against green peach aphid (Myzus persicae) Chinese cabbage was planted in plastic pots with a diameter of 8 cm and a height of 8 cm, and the number of parasites in each pot was counted. The compound of the present invention was dispersed in water and diluted to a 500 ppm drug solution, and the drug solution was sprayed on the stems and leaves of Chinese cabbage planted in the pots and dried in air. The pots were stored in a greenhouse, and the number of parasites of the green peach aphid infesting each Chinese cabbage was counted 6 days after the drug spraying, and the control value was calculated according to the following formula and judged according to the following criteria. The comparative test compounds were also tested in the same manner, and the control values ​​were calculated and evaluated. As a result of this test, the compounds of the present invention and the comparative compounds showed activity of B or higher.

[0133]

number

[0134] Ta: Number of parasites before spraying in the treated area T: Number of parasites in the treated area after spraying Ca: Number of parasites before spraying in untreated area C: Number of parasites after spraying in the untreated area

[0135] Judgment criteria A: Control value 100% B: Control value 99%~90% C: Control value 89%-80% D: Control value 79%~50%

[0136] Test Example 2. Insecticidal test against the small brown planthopper (Laodelphax striatellus) The compound of the present invention was dispersed in water and diluted to a 500 ppm solution. Rice seedlings (variety: Nipponbare) were immersed in the solution for 30 seconds and air-dried, then placed in glass test tubes and inoculated with 10 third-instar larvae of the striate brown planthopper, followed by cotton plugging. Eight days after inoculation, the number of dead and alive insects was counted, and the corrected mortality rate was calculated from the following formula and judged according to the following criteria. The comparative test compounds were also tested in the same manner, and the corrected mortality rate was calculated and evaluated. As a result of this test, the compounds of the present invention and the comparative compounds showed activity of B or higher.

number

[0137] Test Example 3. Insecticidal test against diamondback moth (Plutella xylostella) Adult diamondback moths were released onto Chinese cabbage seedlings to allow them to lay eggs, and two days after the release, the Chinese cabbage seedlings with the eggs were immersed for about 30 seconds in a drug solution containing the compound of the present invention as an active ingredient diluted to 500 ppm, and after air drying, were left to stand in a thermostatic chamber at 25°C. Six days after immersion in the drug solution, the number of surviving insects was counted, and the corrected insect mortality rate was calculated using the following formula and judged according to the following criteria. Triplicate run. The comparative test compounds were also tested in the same manner, and the corrected mortality rate was calculated and evaluated. As a result of this test, the compounds of the present invention and the comparative compounds showed activity of B or higher.

[0138]

number

[0139] Test Example 4. Insecticidal test against Spodoptera litura Cabbage leaf pieces (variety: Shikisaku) were immersed for about 30 seconds in a solution of a drug containing the compound of the present invention as an active ingredient diluted to 500 ppm, air-dried, then placed in a plastic petri dish with a diameter of 9 cm, inoculated with second-instar larvae of Spodoptera litura, covered, and allowed to stand in a thermostatic chamber at 25°C. Eight days after inoculation, the number of surviving insects was counted, the corrected insect mortality rate was calculated using the following formula, and the results were judged according to the following criteria. 10 insects per group, 3 replicates. The comparative test compounds were also tested in the same manner, and the corrected mortality rate was calculated and evaluated in the same manner. As a result of this test, the compounds of the present invention and the comparative compounds showed activity of B or higher.

number

[0140] Test Example 5. Safety test for honeybees (acute oral toxicity test) Seven to ten adult European honeybees (Apis mellifera) were released into a plastic insect cage (8cm x 12cm x 20cm) and after fasting for 2 hours, a 50% sucrose solution (20μl per bee) containing a given concentration of drug solution was administered to the bee using a 1.5ml microtube as drug bait. Four hours after administration, the drug bait was removed and the amount of drug ingested per bee was calculated from the remaining amount. At the same time, the bees were given a sufficient amount of 50% sucrose solution and kept under conditions of 25℃, H55-75%, and 16L8D. The number of dead and abnormal bees was counted 24, 48, and 96 hours later to determine the median lethal dose (LD 50 The untreated group was fed a 50% sucrose solution containing no drugs and reared under the same conditions as the drug-treated group. As a result of this test, the LD of the compound of the present invention for one adult honeybee after 96 hours was 50 The LD value of the comparative compound was 2.04 μg. 50 The values ​​were 0.007 to 0.01 μg. In the untreated area, there were no dead or abnormal insects even after 96 hours. The results of this test show that the compounds of the present invention are 200 times or more safer for honeybees than the comparative compounds.

[0141] From the results of the above Test Examples 1 to 5, it is evident that the compound of the present invention is safe to honeybees and has excellent effects against pests in the agricultural and horticultural fields. [Industrial Applicability]

[0142] The pyrimidinyltriazole compound or a salt thereof of the present invention can be used as an agricultural and horticultural pest control agent which is safe for honeybees.

Claims

1. Formula (I) 【Chemistry 1】 A compound represented by the formula:

2. 10. An agricultural and horticultural pest control agent comprising the compound or a salt thereof according to claim 1 as an active ingredient.

3. A method for using the agricultural and horticultural pest control agent according to claim 2, which comprises applying an effective amount of the agricultural and horticultural pest control agent to a target plant or soil.

4. 3. A method for controlling pests in the agricultural and horticultural fields, comprising applying an effective amount of the agricultural and horticultural pest control agent according to claim 2 to a target plant or soil.

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