Crystals of 2-[5-cyclopropyl-3-(ethanesulfonyl)pyridin-2-yl]-5-(trifluoromethanesulfonyl)-1,3-benzoxazole, pest control agent containing said crystals, and methods for using same

Abstract

The present invention addresses the problem of providing: novel crystals of a compound represented by formula (1); a pest control agent (for example, an agricultural / horticultural pest control agent) containing said crystals; and methods for using the same. Provided are crystals of a compound represented by formula (1), the crystals having diffraction peaks at diffraction angles (2θ) of 9.4 ± 0.2°, 13.4 ± 0.2°, 16.1 ± 0.2°, 18.6 ± 0.2°, and 22.5 ± 0.2° in a powder X-ray diffraction spectrum.

Description

Crystals of 2-[5-cyclopropyl-3-(ethanesulfonyl)pyridine-2-yl]-5-(trifluoromethanesulfinyl)-1,3-benzoxazole, insecticides containing the crystals, and methods for using the same.

[0001] The present invention relates to crystals of 2-[5-cyclopropyl-3-(ethanesulfonyl)pyridine-2-yl]-5-(trifluoromethanesulfinyl)-1,3-benzoxazole (hereinafter referred to as compound (1)), and pest control agents containing these crystals (for example, pest control agents for agricultural and horticultural use), as well as methods for using them. The present invention also relates to a method for producing these crystals.

[0002] 2-[5-cyclopropyl-3-(ethanesulfonyl)pyridine-2-yl]-5-(trifluoromethanesulfinyl)-1,3-benzoxazole (compound (1)) is known as cybenzoxasulfyl (see Non-Patent Document 1). Patent Document 1 describes that compound (1) is useful as an insecticide for agricultural and horticultural pests, and Patent Documents 2 and 3 describe methods for producing compound (1). Furthermore, Patent Document 4 describes one of the crystals that compound (1) can produce (hereinafter referred to as type A crystal) and a method for producing said crystal. However, none of these documents disclose the crystal of the present invention described below or its production method.

[0003] International Publication No. 2017 / 146226 Pamphlet, International Publication No. 2019 / 009387 Pamphlet, Japanese Patent Publication No. 2020-172469, International Publication No. 2024 / 085225 Pamphlet

[0004] Compendium of Pesticide Common Names, "Index of New ISO Common Names," [Accessed September 25, 2024], Internet <URL: http: / / www.bcpcpesticidecompendium.org / index_new_frame.html>

[0005] The present invention aims to provide a novel crystal (hereinafter sometimes referred to as a B-type crystal) of compound (1) represented by the following formula (1), which has excellent control effects against pests in the fields of agriculture and horticulture, and a method for producing the same.

[0006] The inventors of this invention have diligently conducted research to develop a compound that has excellent control effects against pests in the fields of agriculture and horticulture, and as a result have discovered a novel B-type crystal of compound (1) represented by the following formula (1) of the present invention, thereby completing the present invention.

[0007] That is, the present invention is [1] Formula (1): A crystal of the compound represented by [1], wherein in a powder X-ray diffraction spectrum, the (B-type) crystal has diffraction peaks at diffraction angles (2θ) of at least 9.4±0.2°, 13.4±0.2°, 16.1±0.2°, 18.6±0.2° and 22.5±0.2°; [2] The (B-type) crystal according to [1], which is shown to have a melting point of 123-135°C in differential scanning calorimetry (DSC) (i.e., the melting point measured by DSC is 123-135°C); [3] In an infrared absorption spectrum, the wavenumber is 1312±4 cm －１ , 1174±4cm －１ , 1135±4cm －１ , 1073±4cm －１ , 845±4cm －１ , 818±4cm －１ 725±4cm －１ and 670±4cm －１ A (Type B) crystal according to [1] or [2] having a peak at the position of [4] formula (1): A method for producing (Type B) crystals of a compound represented by formula (1), characterized by suspending the compound represented by formula (1) in a solvent containing at least one halogenated hydrocarbon (for example, a solvent containing at least one halogenated hydrocarbon), and stirring the resulting slurry (including the step of stirring the resulting slurry), as described in any one of [1] to [3], [5] Formula (1): A method for producing (Type B) crystals of a compound represented by formula (1), characterized by dissolving the compound represented by formula (1) in a solvent containing at least one selected from the group consisting of aromatic hydrocarbons and esters (for example, at least one solvent selected from the group consisting of aromatic hydrocarbons and esters), and precipitating crystals from the obtained solution (including a step of precipitating crystals from the obtained solution), wherein seed crystals may be added in the step of precipitating the crystals, a method for producing (Type B) crystals according to any one of [1] to [3], a pest control agent (for example, an agricultural and horticultural pest control agent) characterized by containing the crystals according to any one of [6] [1] to [3] as an active ingredient, a method for using a pest control agent (for example, an agricultural and horticultural pest control agent) characterized by treating a target plant or soil with an effective amount of the pest control agent (for example, an agricultural and horticultural pest control agent) according to [7] [6], The present invention relates to a method for controlling (e.g., killing) pests (e.g., agricultural and horticultural pests), characterized by applying an effective amount of the pest control agent described in [8] and [6] (e.g., a pest control agent for agricultural and horticultural use) to a target plant or soil.

[0008] The B-type crystal of compound (1) represented by formula (1) of the present invention has a control (e.g., insecticidal) effect against pests in the fields of agriculture and horticulture. In particular, the B-type crystal of compound (1) represented by formula (1) of the present invention not only has an excellent effect as a pest control agent for agriculture and horticulture, but also has an effect (control effect) against pests that parasitize pets other than humans, such as dogs and cats, or livestock such as cattle and sheep.

[0009] This graph shows the powder X-ray diffraction spectrum of the B-type crystal of compound (1) produced in Manufacturing Example 1. This graph shows the differential scanning calorimetry (DSC) results of the B-type crystal of compound (1) produced in Manufacturing Example 1. This graph shows the infrared absorption spectrum of the B-type crystal of compound (1) produced in Manufacturing Example 1. This graph shows the powder X-ray diffraction spectrum of the B-type crystal of compound (1) produced in Manufacturing Example 2. This graph shows the differential scanning calorimetry (DSC) results of the B-type crystal of compound (1) produced in Manufacturing Example 2. This graph shows the powder X-ray diffraction spectrum of the B-type crystal of compound (1) produced in Manufacturing Example 3. This graph shows the differential scanning calorimetry (DSC) results of the B-type crystal of compound (1) produced in Manufacturing Example 3.

[0010] In this specification, unless otherwise specified, "crystal" refers to a solid formed by the regular arrangement of constituent atoms, ions, molecules, etc., in three dimensions, and is not an amorphous solid that does not have a regular internal structure.

[0011] The B-type crystals of compound (1) of the present invention can be produced, for example, by crystallization methods well known in related fields, such as slurry methods and crystallization methods. Specifically, they can be produced by the following methods, but the methods for producing the crystals are not limited to these.

[0012] Method 1 for producing type B crystals of compound (1): By suspending compound (1), synthesized according to the method described in Patent Documents 1, 2, 3, or 4, in a solvent and stirring the resulting slurry, type B crystals can be produced.

[0013] The amount of solvent used in this manufacturing method should be sufficient to suspend compound (1), and can be appropriately selected from the range of 0.1 L to 5 L per mole of compound (1).

[0014] In this manufacturing method, stirring should normally be performed within a range of 10°C to 80°C, and the stirring time should be appropriately selected from a range of 1 hour to 350 hours.

[0015] The solvents used in this manufacturing method include, for example, aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; nitrated aromatic hydrocarbons such as nitrobenzene; linear or cyclic aliphatic hydrocarbons such as pentane, hexane, heptane, cyclopentane, and cyclohexane; linear or cyclic ketones such as acetone, 2-butanone, and cyclohexanone; linear or cyclic ethers such as diethyl ether, tert-butyl methyl ether, tetrahydrofuran, and dioxane; methanol, ethanol, and 1-butyl ether. Examples of suitable solvents include linear or cyclic alcohols such as ropanol, 2-propanol, and cyclohexanol; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, and 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; esters such as methyl acetate, ethyl acetate, and butyl acetate; amides such as formamide, N,N-dimethylformamide, and N,N-dimethylacetamide; dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and water. These solvents can be used individually or in combination of two or more. Among these solvents, halogenated hydrocarbons are preferred, and chloroform is more preferred.

[0016] Method 2 for producing type B crystals of compound (1): By dissolving compound (1), synthesized according to the method described in Patent Documents 1, 2, 3, or 4, in a solvent, cooling the resulting solution, and adding seed crystals as needed and stirring, type B crystals can be produced.

[0017] The amount of solvent used in this manufacturing method should be sufficient to dissolve compound (1), and can usually be appropriately selected from the range of 0.1 L to 5 L per mole of compound (1). The dissolution temperature can also be appropriately selected from the range of room temperature to 100°C.

[0018] In this manufacturing method, stirring should normally be performed within a range of 10°C to 50°C, and the stirring time should be appropriately selected from a range of 1 hour to 48 hours.

[0019] In this production method, a seed crystal of the B-form crystal of compound (1) can be added as necessary. When adding the seed crystal of the B-form crystal of compound (1), the temperature can usually be appropriately selected from the range of 10°C to 50°C, and the amount of the seed crystal can be appropriately selected from the range of 0.001 to 10% by weight based on compound (1). The seed crystal may be separately prepared in advance using the production method of the present invention.

[0020] Examples of the solvent used in this production method include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; nitrated aromatic hydrocarbons such as nitrobenzene; linear or cyclic aliphatic hydrocarbons such as pentane, hexane, heptane, cyclopentane, and cyclohexane; linear or cyclic ketones such as acetone, 2-butanone, and cyclohexanone; linear or cyclic ethers such as diethyl ether, tert-butyl methyl ether, tetrahydrofuran, and dioxane; linear or cyclic alcohols such as methanol, ethanol, 1-propanol, 2-propanol, and cyclohexanol; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, and 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; esters such as methyl acetate, ethyl acetate, and butyl acetate; amides such as formamide, N,N-dimethylformamide, and N,N-dimethylacetamide; dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, water, etc. These solvents can be used alone or in combination of two or more. Among these solvents, aromatic hydrocarbons or esters are preferred, and toluene or ethyl acetate is more preferred.

[0021] The B-form crystal of compound (1) obtained according to the above method has diffraction peaks at least at diffraction angles (2θ) of 9.4 ± 0.2°, 13.4 ± 0.2°, 16.1 ± 0.2°, 18.6 ± 0.2°, and 22.5 ± 0.2° in the powder X-ray diffraction spectrum. The B-form crystal of compound (1) obtained according to the above method shows a melting point of 123 to 135°C in differential scanning calorimetry (DSC), and / or in the infrared absorption spectrum, the wave number is 1312 ± 4 cm －１, 1174±4cm －１ , 1135±4cm －１ , 1073±4cm －１ , 845±4cm －１ , 818±4cm －１ 725±4cm －１ and 670±4cm －１ It has a peak at this position.

[0022] In the present invention, powder X-ray diffraction, differential scanning calorimetry, infrared spectroscopy, and the like are effective for identifying crystals, but the invention is not limited to these.

[0023] In this specification, powder X-ray diffraction was measured under the following conditions: Instrument name: Mini Flex (manufactured by Rigaku Corporation) X-ray: Cu-Kα (40kV, 15mA) Scanning range: 5-90° Sampling width: 0.01° Scanning speed: 5° / min

[0024] In this specification, differential scanning calorimetry (DSC) was performed under the following conditions: Instrument name: DSC25 (manufactured by TA Instruments Inc.) Sample cell: SUS gold plated Temperature range: 30°C to 200°C (heating rate: 10°C / min)

[0025] In this specification, Fourier transform infrared spectroscopy (FT-IR) was measured under the following conditions: Instrument name: NICOLET iS20 (manufactured by thermo scientific) Measurement method: ATR method Number of integrations: 16 Resolution: 4 cm －１

[0026] A pest control agent (for example, an agricultural and horticultural pest control agent) containing type B crystals of the compound represented by formula (1) of the present invention as an active ingredient can be applied to the control of various agricultural and forestry pests, horticultural pests, forest pests, stored grain pests, household pests, sanitary pests, nematodes, and other pests that damage rice, fruit trees, vegetables, other crops, and flowers.

[0027] Examples of the above-mentioned pests, nematodes, etc. include the following: Lepidopteran (butterfly) pests include, for example, the green stinging moth (Parasa consocia), the red cutworm (Anomis mesogona), the swallowtail butterfly (Papilio xuthus), the adzuki bean pod moth (Matsumuraeses azukivora), the adzuki bean leafroller (Ostrinia scapulalis), the African armyworm (Spodoptera exempta), the fall webworm (Hyphantria cunea), the corn borer (Ostrinia furnacalis), the millet moth (Pseudaletia separata), the clothes moth (Tinea translucens), the rush weed moth (Bactra furfurana), the common skipper butterfly (Parnara guttata), the rice leaf roller moth (Marasmia exigua), the rice leaf roller (Parnara guttata), and the rice armyworm (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, Archips (Xylosteanus), turnip moth (Agrotis segetum), sweet potato leafroller moth (Tetramoera schistaceana), swallowtail butterfly (Papilio machaon hippocrates), yellow-spotted bat (Endoclyta)(sinensis), silver leaf miner (Lyonetia prunifoliella), golden leaf miner (Phyllonorycter ringoneella), chestnut moth (Cydia kurokoi), chestnut green leaf miner (Eucoenogenes aestuosa), grapeberry moss (Lobesia botrana), black-skinned green stinging moth (Latoia sinica), black two-spotted leaf moth (Euzophera batangensis), mulberry leaf roller (Phalonidia mesotypa), mulberry spotted moth (Spilosoma imparilis), mulberry leaf roller (Glyphodes pyloalis), mulberry leaf roller (Olethreutes mori), clothes moth (Tineola bisselliella), bat moth (Endoclyta excrescens), black moth (Nemapogon) granellus), clearwing moth (Synanthedon hector), codling moth (Cydia pomonella), diamondback moth (Plutella xylostella), rice leaf roller (Cnaphalocrocis medinalis), southern pink borer (Sesamia calamistis), sun leaf roller (Scirpophaga incertulas), sod web moth (Pediasia teterrellus), potato moth (Phthorimaea operculella), notodontid moth (Stauropus fagi persimilis), white spotted rice leaf roller (Etiella zinckenella), white spotted armyworm (Spodoptera exigua), white spotted bat (Palpifer sexnotata), white armyworm (Spodoptera mauritia), rice white leaf roller (Scirpophaga (innotata), White-spotted moth (Xestia c-nigrum), Striped cutworm (Spodoptera depravata), Striped rice moth (Ephestia kuehniella), Plum moth (Angerona prunaria), Black-backed prominent moth (Clostera anastomosis), Soybean looper (Pseudoplusia(includens), soybean pod moth (Matsumuraeses falcana), tobacco moth (Helicoverpa assulta), cabbage leafroller (Autographa nigrisigna), cabbage cutworm (Agrotis ipsilon), tea tortrix moth (Euproctis pseudoconspersa), tea leafroller moth (Adoxophyes orana), tea leafroller moth (Caloptilia theivora), tea leafroller moth (Homona magnanima), tea leaf moth (Ephestia elutella), tea bagworm moth (Eumeta minuscula), red-spotted moth (Clostera anachoreta), cudweed moth (Heliothis maritima), long-nosed leafroller moth (Sparganothis pilleriana), corn moth (Busseola fusca), tussock moth (Euproctis subflava), large geometrid moth (Biston) (robustum), tomato leaf moth (Tuta absoluta), tomato fruit worm (Heliothis zea), white-backed moth (Aedia leucomelas), pear slug moth (Narosoideus flavidorsalis), pear worm (Viminia rumicis), pear dwarf moth (Bucculatrix pyrivorella), pear leaf moth (Grapholita molesta), pear leaf moth (Spulerina astaurota), pear leaf moth (Ectomyelois pyrivorella), rice leaf moth (Chilo suppressalis), onion moth (Acrolepiopsis sapporensis), Indian meal moth (Plodia interpunctella), diamondback moth (Hellula undalis), bakuga (Sitotroga cerealella), beet armyworm (Spodoptera (litura), a species of leafroller (Eucosma aporema), rose leafroller (Acleris comariana), small black stinging moth (Scopelodes contractus), small white tussock moth (Orgyia)thyellina), fall army worm (Spodoptera frugiperda), peanut leafroller (Ostrinia zaguliaevi), two-banded leafroller (Naranga aenescens), two-spotted hook-winged moth (Andraca bipunctata), grape clearwing moth (Paranthrene regalis), grape hawk moth (Acosmeryx castanea), grape leafminer (Phyllocnistis toparcha), grape leaf tortrix (Endopiza viteana), grape leaf tortrix (Eupoecillia ambiguella), velvet bean caterpillar (Anticarsia gemmatalis), narrow-winged gray leaf tortrix (Cnephasia cinereipalpana), gypsy moth (Lymantria dispar), pine processionary moth (Dendrolimus spectabilis), bean pod borer (Leguminivora glycinivorella), bean leafminer (Maruca testulalis), bean pod moth (Matsumuraeses phaseoli), bean leaf moth (Caloptilia soyella), citrus leafminer (Phyllocnistis citrella), citrus leafminer (Omiodes indicate), variegated leafroller (Archips fuscocupreanus), three-spotted golden moth (Acanthoplusia agnata), bagworm moth (Bambalina sp.), peach fruit moth (Carposina niponensis), peach leafminer (Conogethes punctiferalis), peach clearwing moths (Synanthedon sp.), peach leafminer (Lyonetia clerkella), swallowtail butterfly (Papilio helenus), clouded yellow butterfly (Colias erate) White butterflies such as Pieris rapae crucivora, Pieris rapae, Euproctis similis, and AcrolepiopsisSuzukiella, European corn borer (Ostrinia nubilalis), armyworm (Mamestra brassicae), mugwort geometrid moth (Ascotis selenaria), mugwort leaf roller (Phtheochroides clandestina), apple leaf roller (Hoshinoa adumbratana), apple dwarf moth (Odonestis pruni japonensis), apple scolyte moth (Triaena intermedia), apple corn leaf roller (Adoxophyes orana fasciata), apple fruit moth (Grapholita inopinata), apple white leaf roller (Spilonota ocellana), apple gray leaf roller (Spilonota lechriaspis), apple leaf roller moth (Illiberis pruni), apple fruit moth (Argyresthia conjugella), apple leaf roller (Caloptilia) Examples include the cactus zachrysa, the apple leafroller (Archips breviplicanus), the cotton leaf cutter (Anomis flava), the cotton earworm (Pectinophora gossypiella), the cotton leaf moth (Notarcha derogata), the cotton leaf moth (Diaphania indica), the false tobacco budworm (Heliothis virescens), and the cotton moth (Earias cupreoviridis).

[0028] Examples of Hemiptera (true bug) pests include the green stink bug (Nezara antennata), the red-striped stink bug (Stenotus rubrovittatus), the red-striped stink bug (Graphosoma rubrolineatum), the red-bearded green stink bug (Trigonotylus coelestialium), the red-legged stink bug (Aeschynteles maculatus), the red-spotted stink bug (Creontiades pallidifer), the red-spotted stink bug (Dysdercus cingulatus), the red-spotted scale insect (Chrysomphalus ficus), the red-spotted scale insect (Aonidiella aurantii), and the cicada (Graptopsaltria). nigrofuscata), American stink bug (Blissusleucopterus), Icerya scale insect (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's stink bug (Stariodes iwasakii), pale round scale insect (Aspidiotus destructor), pale green stink bug (Taylorilygus pallidulus), plum aphid (Myzus mumecola), plum white scale insect (Pseudaulacaspis) Prunicola, pea aphid (Acyrthosiphon pisum), large spider bug (Anacanthocoris striicornis), large black stink bug (Ectometopterus micantulus), large spiny white-spotted bug (Eysarcoris lewisi), large stink bug (Molipteryx fuliginosa), large leafhopper (Cicadella viridis), land aphid (Rhopalosophum)rufiabdominalis), olive scale insect (Saissetia oleate), greenhouse whitefly (Trialeurodes vaporariorum), oak leafhopper (Aguriahana quercus), mirid bugs (Lygus spp.), chaff aphid (Euceraphis punctipennis), citrus scale insect (Andaspis kashicola), citrus scale insect (Coccus pseudomagnoliarum), citrus long-winged stink bug (Cavelerius saccharivorus), chrysanthemum lace bug (Galeatus spinifrons), chrysanthemum long-horned aphid (Macrosiphoniella sanborni), yellow scale insect (Aonidiella citrina), brown marmorated stink bug (Halyomorpha Mista), Stephanitis fasciicarina, Trioza camphorae, Leptocorisa chinensis, Trioza quercicola, Uhlerites latius, Erythroneura comes, Paromius exiguus, Dulappidiotus claviger, Nephotettix nigropictus, Halticiellus insularis, Perkinsiella saccharicida, Psylla malivorella, Anomomeura Mori), Mulberry scale insect (Pseudococcus longispinis), Mulberry white scale insect (Pseudaulacaspis pentagona), Mulberry cottony scale insect (Pulvinaria kuwacola), Small green stink bug (Apolygus lucorum), Small gourd-shaped stink bug (Togohemipterus), citrus aphid (Toxoptera aurantii), sugarcane mealybug (Saccharicoccus sacchari), sugarcane woolly aphid (Geoica lucifuga), sugar planthopper (Numata muiri), San Jose scale insect (Comstockaspis perniciosa), citrus snow scale insect (Unaspis citri), potato longhorn aphid (Aulacorthum solani), white-spotted stink bug (Eysarcoris ventralis), silverleaf whitefly (Bemisia argentifolii), white leafhopper (Cicadella spectra), white round scale insect (Aspidiotus hederae), clear-spotted stink bug (Liorhyssus) hyalinus), black-backed psyllid (Calophya nigridorsalis), white-backed planthopper (Sogatella furcifera), broad bean aphid (Megoura crassicauda), radish aphid (Brevicoryne brassicae), soybean aphid (Aphis glycines), Taiwanese spider bug (Leptocorisa oratorius), Taiwanese leafhopper (Nephotettix virescens), Taiwanese long-horned aphid (Uroeucon formosanum), tobacco bug (Cyrtopeltis tennuis), tobacco whitefly (Bemisia tabaci), tea scale insect (Lecanium persicae), tea black-spotted scale insect (Parlatoria theae), tea round scale insect (Pseudaonidia) Paeoniae), Empoasca onukii, Plautia stali, Dysaphis tulipae, Macrosiphum euphorbiae, Stephanitis pyrioides, Ceroplastesceriferus), camellia scale insect (Parlatoria camelliae), green leafhopper (Apolygus spinolai), leafhopper (Nephotettix cincticeps), stink bug (Glaucias subpunctatus), sugar beet leafhopper (Orthotylus flavosparsus), corn aphid (Rhopalosiphum maidis), corn planthopper (Peregrinus maidis), spiny white-spotted stink bug (Eysarcoris parvus), bed bug (Cimex lectularius), fir psyllid (Psylla abieti), brown planthopper (Nilaparvata lugens), pittosporum psyllid (Psylla tobirae), long-tailed stink bug (Eurydema rugosum), pear aphid (Schizaphis) Pyricola, pear psyllid (Psylla pyricola), pear black-spotted scale insect (Parlatoreopsis pyri), pear lace bug (Stephanitis nashi), pear mealybug (Dysmicoccus wistariae), pear white scale insect (Lepholeucaspis japonica), pear round aphid (Sappaphis piri), false radish aphid (Lipaphis erysimi), onion aphid (Neotoxoptera formosana), rhombic aphid (Rhopalosophum nymphaeae), rose leafhopper (Edwardsianarosae), rose leafhopper (Pinnaspisaspidistrae), alder psyllid (Psylla alni), alder leafhopper (Speusotettix subfusculus), Alnetoidia alneti, Sogatella panicicola, Adelphocoris lineolatus, Dysdercus poecilus, Parlatoria ziziphi, Uhlerites(debile), small planthopper (Laodelphax striatellus), small long-horned bug (Eurydema pulchrum), small stink bug (Cletus trigonus), small two-spotted froghopper (Clovia punctata), small leafhoppers (Empoasca sp.), flat scale insect (Coccus hesperidum), flat gourd-shaped long-horned bug (Pachybrachius luridus), Fuji mealybug (Planococcus kraunhiae), two-striped stink bug (Stenotus binotatus), two-spotted leafhopper (Arboridia apicalis), two-spotted leafhopper (Macrosteles fascifrons), spotted stink bug (Dolycoris baccarum), spotted black stink bug (Adelphocoris) Triannulatus), grape aphid (Viteus vitifolii), physalis stink bug (Acanthocoris sordidus), slender stink bug (Leptocorisa acuta), slender long-winged stink bug (Macropes obnubilus), slender needle bug (Cletus punctiger), slender stink bug (Riptortus clavatus), potato pistil (Paratrioza cockerelli), froghopper (Aphrophora costalis), pine leafhopper (Lygus disponsi), spotted leafhopper (Lygus saundersi), pine mealybug (Crisicoccus pini), pine leafhopper (Empoasca abietis), pine mealybug (Crisicoccus matsumotoi), bean aphid (Aphis craccivora), round stink bug (Megacopta punctatissimum), white-spotted stink bug (Eysarcoris guttiger), citrus scale insect (Lepidosaphes beckii), citrus psyllid (Diaphorina citri), citrus black aphid (Toxoptera citricidus), citrus mealybug (PlanococcusCitrus whitefly (Dialeurodes citri), citrus spiny whitefly (Aleurocanthus spiniferus), citrus mealybug (Pseudococcus citriculus), citrus leafhopper (Zyginella citri), citrus cottony scale (Pulvinaria citricola), citrus flat scale (Coccus discrepans), citrus round scale (Pseudaonidia duplex), citrus cottony scale (Pulvinaria aurantii), dogwood scale (Lecanium corni), southern green stink bug (Nezara viridula), wheat stink bug (Stenodema calcaratum), wheat aphid (Rhopalosiphum padi), wheat long-horned aphid (Sitobion) akebiae), wheat aphid (Schizaphis graminum), wheat leafhopper (Sorhoanus tritici), straw chrysanthemum aphid (Brachycaudus helichrysi), purple stink bug (Carpocoris purpureipennis), peach aphid (Myzus persicae), peach powder aphid (Hyalopterus pruni), willow aphid (Aphis farinose yanagicola), willow lace bug (Metasalis populi), willow scale insect (Unaspis yanonensis), mountain whitefly (Mesohomotoma camphorae), willow aphid (Aphis spiraecola), apple aphid (Aphis pomi), apple persimmon scale insect (Lepidosaphes Apple psyllid (Psylla mali), apple black stink bug (Heterocordylus flavipes), apple gall aphid (Myzus malisuctus), apple root aphid (Aphidonuguis mali), apple leafhopper (Orientus ishidai), apple green aphid (OvatusExamples include the malicolens, apple mealybug (Eriosoma lanigerum), ruby ​​scale insect (Ceroplastes rubens), and cotton aphid (Aphis gossypii).

[0029] Examples of Coleoptera (beetle) pests include the blue-striped longhorn beetle (Xystrocera globosa), the green-leaved rove beetle (Paederus fuscipes), the green flower beetle (Eucetonia roelofsi), the adzuki bean weevil (Callosobruchus chinensis), the false ant weevil (Cylas formicarius), the alfalfa tadpole weevil (Hypera postica), the rice weevil (Echinocnemus squameus), the rice leaf beetle (Oulema oryzae), the rice leaf beetle (Donacia provosti), the rice water weevil (Lissorhoptrus oryzophilus), the sweet potato leaf beetle (Colasposoma dauricum), and the sweet potato weevil (Euscepes (postfasciatus), bean ladybug (Epilachna varivestis), bean weevil (Acanthoscelides obtectus), Western corn root worm (Diabrotica virgifera virgifera), plum weevil (Involvulus cupreus), cucumber beetle (Aulacophora femoralis), pea weevil (Bruchus pisorum), large 28-spotted ladybug (Epilachna vigintioctomaculata), sea cucumber beetle (Carpophilus dimidiatus), tortoise 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, chestnut weevil (Curculio sikkimensis), chestnut sap beetle (Carpophilus hemipterus), small green flower beetle (Oxycetonia jucunda), corn root worms (Diabrotica spp.), scarab beetle (Mimela)Splendens), rice weevil (Sitophilus zeamais), confused flour beetle (Tribolium castaneum), small rice weevil (Sitophilus oryzae), small confused flour beetle (Palorus subdepressus), powdered beetle (Melolontha japonica), spotted longhorn beetle (Anoplophora malasiaca), darkling beetle (Neatus picipes), Colorado leaf beetle (Leptinotarsa ​​decemlineata), Southern corn root worm (Diabrotica undecimpunctata howardi), grass weevil (Sphenophorus venatus), fourteen-spotted long-necked leaf beetle (Crioceris quatuordecimpunctata), plum weevil (Conotrachelus nenuphar), radish weevil (Ceuthorhynchidius) albosuturalis), radish beetle (Phaedon brassicae), cigarette beetle (Lasioderma serricorne), small powder weevil (Sitona japonicus), brown beetle (Adoretus tenuimaculatus), brown darkling beetle (Tenebrio molitor), brown leaf beetle (Basilepta balyi), clover weevil (Hypera nigrirostris), dwarf beetle (Chaetocnema concinna), golden beetle (Anomala cuprea), long-horned beetle (Heptophylla picea), 28-spotted ladybug (Epilachna vigintioctopunctata), northern corn root worm (Diabrotica longicornis), flower beetle (Eucetonia pilifera), horsehair worms (Agriotes) spp. ), carpet beetle (Attagenus unicolor japonicus), leaf beetle (Pagria signata), scarab beetle (Anomala rufocuprea), false flour beetle (Palorusratzeburgii), darkling beetle (Alphitobius laevigatus), varied carpet beetle (Anthrenus verbasci), flat bark beetle (Lyctus brunneus), flat grain beetle (Tribolium confusum), two-striped leaf beetle (Medythia nigrobilineata), grape longhorn beetle (Xylotrechus pyrrhoderus), potato free beetle (Epitrix cucumeris), pine bark beetle (Tomicus piniperda), Japanese pine sawyer beetle (Monochamus alternatus), bean beetle (Popillia japonica), bean blister beetle (Epicauta gorhami), maze weevil (Sitophilus zeamais), peach weevil (Rhynchites) Examples include the weevil *Heroes*, the vegetable weevil (Listroderes costirostris), the four-spotted bean weevil (Callosobruchus maculatus), the apple powder weevil (Phyllobius armatus), the apple flower weevil (Anthonomus pomorum), the blue leaf beetle (Linaeidea aenea), and the cotton weevil (Anthonomus grandis).

[0030] Diptera (flies) pests include, for example, Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, Hydrellia sasakii, Agromyza oryzae, Hydrellia griseola, Hydrellia griseola, Ophiomyia phaseoli, Dacus cucurbitae, and Drosophila. Phorid flies such as *Suzukii*, *Rhacochlaena japonica*, *Muscina stabulans*, *Megaselia spiracularis*, *Clogmia albipunctata*, *Tipula aino*, *Phormia regina*, *Culex tritaeniorhynchus*, *Anopheles sinensis*, *Hylemya brassicae*, *Asphondylia sp.*, *Delia platura*, *Delia antiqua*, *Rhagoletis cerasi*, and *Culex pipiens molestus*. Forskal), Mediterranean fruit fly (Ceratitis capitata), small black fungus gnat (Bradysia agrestis), sugar beet leafminer (Pegomya cunicularia), tomato leafminer (Liriomyza sativae), eggplant leafminer (Liriomyza bryoniae), green onion leafminer (Chromatomyia horticola), onion leafminer (Liriomyza chinensis), tropical house mosquito (Culex)Examples include *Aedes quinquefasciatus*, *Aedes aegypti*, *Aedes albopictus*, *Liriomyza trifolii*, *Liriomyza sativae*, *Dacus dorsalis*, *Dacus tsuneonis*, *Sitodiplosis mosellana*, *Meromuza nigriventris*, *Anastrepha ludens*, and *Rhagoletis pomonella*.

[0031] Examples of Hymenoptera (bee and wasp) pests include the reticulated ant (Pristomyrmex pungens), parasitic wasps, house ant (Monomorium pharaohnis), big-headed ant (Pheidole noda), turnip sawfly (Athalia rosae), chestnut gall wasp (Dryocosmus kuriphilus), black ant (Formica fusca japonica), hornets, black turnip sawfly (Athalia infumata infumata), rose sawfly (Arge pagana), Japanese turnip sawfly (Athalia japonica), leafcutter ant (Acromyrmex spp.), fire ant (Solenopsis spp.), apple sawfly (Arge mali), and blue ant (Ochetellus glaber).

[0032] Examples of orthopteran (grasshopper) pests include the grasshopper (Homorocoryphus lineosus), mole cricket (Gryllotalpa sp.), small grasshopper (Oxya hyla intricata), short-winged grasshopper (Oxya yezoensis), migratory locust (Locusta migratoria), long-winged grasshopper (Oxya japonica), small grasshopper (Homorocoryphus jezoensis), and field cricket (Teleogryllus emma).

[0033] Examples of thrips include the red-banded thrips (Selenothrips rubrocinctus), the rice thrips (Stenchaetothrips biformis), the rice tube thrips (Haplothrips aculeatus), the oak tube thrips (Ponticulothrips diospyrosi), the yellow flower thrips (Thrips flavus), the grass yellow thrips (Anaphothrips obscurus), the black tube thrips (Liothrips floridensis), the gladiolus thrips (Thrips simplex), the black flower thrips (Thrips nigropilosus), the croton thrips (Heliothrips haemorrhoidalis), and the mulberry thrips (Pseudodendrothrips). mori), cosmos thrips (Microcephalothrips abdominalis), long-tailed thrips (Leeuwenia pasanii), round thrips (Litotetothrips pasaniae), citrus thrips (Scirtothrips citri), Chinese thrips (Haplothrips chinensis), soybean thrips (Mycterothrips glycines), soybean thrips (Thrips setosus), tea yellow thrips (Scirtothrips dorsalis), tea black thrips (Dendrothrips minowai), clover thrips (Haplothrips niger), onion thrips (Thrips tabaci), onion black thrips (Thrips Thrips alliorum), flower thrips (Thrips hawaiiensis), flower thrips (Haplothrips kurdjumovi), thick-bearded thrips (Chirothrips manicatus), flat-headed flower thrips (Frankliniella intonsa), loquat flower thrips (Thrips coloratus), orange yellow thrips (Franklinella occidentalis), southern yellow thrips (Thripssuch as Thrips palmi, Frankliniella lilivora, Liothrips vaneeckei, etc.

[0034] Examples of tick-related pests 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 the redback spider (*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), Southern spider mite (Brevipalpus phoenicis), Ear mite (Octodectes cynotis), House dust mite (Dermatophagoides ptrenyssnus), Japanese tick (Haemaphysalis flava), Japanese tick (Ixodes)Examples include *Phyllocoptruta citri*, *Aculus schlechtendali*, *Panonychus ulmi*, *Amblyomma americanum*, and *Dermanyssus gallinae*, *Rhyzoglyphus robini*, and a species of *Sancassania sp.*.

[0035] Examples of termite pests include the Amami termite (Reticulitermes miyatakei), the American drywood termite (Incisitermes minor), the Formosanus termite (Coptotermes formosanus), the Japanese white termite (Hodotermopsis japonica), the Kanmon termite (Reticulitermes sp.), the yellow-legged termite (Reticulitermes flaviceps amamianus), the Glyptotermes kushimensis, the Koshu termite (Coptotermes guangzhoensis), the Koshun termite (Neotermes koshunensis), the Kodama termite (Glyptotermes kodamai), the Satsuma termite (Glyptotermes satsumensis), the Daikoku termite (Cryptotermes domesticus), and the Taiwanese termite (Odontotermes) Examples include *Formosanus*, *Glyptotermes nakajimai*, *Pericapritermes nitobei*, and *Reticulitermes speratus*.

[0036] As cockroach pests, for example, black cockroach (Periplaneta fuliginosa), German cockroach (Blattella germanica), oriental cockroach (Blatta orientalis), brown cockroach (Periplaneta brunnea), smoky brown cockroach (Blattella lituricollis), Japanese cockroach (Periplaneta japonica), American cockroach (Periplaneta americana), etc. can be mentioned.

[0037] As nematodes, for example, stubby root nematode (Nothotylenchus acris), rice white tip nematode (Aphelenchoides besseyi), root-lesion nematode (Pratylenchus penetrans), northern root-knot nematode (Meloidogyne hapla), southern root-knot nematode (Meloidogyne incognita), potato cyst nematode (Globodera rostochiensis), Javanese root-knot nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), coffee root-lesion nematode (Pratylenchus coffeae), wheat root-lesion nematode (Pratylenchus neglectus), citrus nematode (Tylenchus semipenetrans), etc. can be mentioned.

[0038] As mollusks, for example, golden apple snail (Pomacea canaliculata), African giant snail (Achatina fulica), slug (Meghimatium bilineatum), Lehmann's glass slug (Lehmannina valentiana), tawny garden slug (Limax flavus), Japanese forest slug (Acusta despecta sieboldiana), etc. can be mentioned.

[0039] Furthermore, the pest control agent of the present invention (for example, a pest control agent for agricultural and horticultural use) also has a strong insecticidal effect against other pests, such as the tomato leafminer (Tuta absoluta).

[0040] In addition, animal-parasitic mites that are one of the targets of control include, for example, *Boophilus microplus*, *Rhipicephalus sanguineus*, *Haemaphysalis longicornis*, *Haemaphysalis flava*, *Haemaphysalis campanulata*, *Haemaphysalis concinna*, *Haemaphysalis japonica*, *Haemaphysalis kitaokai*, *Haemaphysalis ias*, *Ixodes ovatus*, *Ixodes nipponensis*, *Ixodes persulcatus*, *Amblyomma testudinarium*, and *Haemaphysalis*. Ticks such as megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis; mites such as Dermanyssus gallinae, Ornithonyssus sylviarum, and Ornithonyssus bursa; Leptotrombidium wichmanni, Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, Neotrombicula autumnalis, Eutrombicula alfreddugesi, and Helenicula Scrub mites such as *miyagawai*;Examples include Cheyletiella yasguri, Cheyletiella parasitivorax, and Cheyletiella blakei; Sarcoptes scabiei, such as Psoroptes cuniculi, Chorioptes bovis, Otodectes cynotis, Sarcoptes scabiei, and Notoedres cati; and Demodex mites, such as Demodex canis.

[0041] Other fleas that are targets for control include, for example, wingless ectoparasitic insects belonging to the order Siphonaptera, more specifically, fleas belonging to the families Pulicidae and Ceratephyllus. Examples of fleas belonging to the family Ceratephyllus include the dog flea (Ctenocephalides canis), cat flea (Ctenocephalides felis), human flea (Pulex irritans), chicken flea (Ceratophyllus gallinae), chicken flea (Echidnophaga gallinacea), cheops' mouse flea (Xenopsylla cheopis), blind mouse flea (Leptopsylla segnis), European mouse flea (Nosopsyllus fasciatus), and Japanese mouse flea (Monopsyllus anisus).

[0042] Furthermore, other ectoparasites that are targets for control include, for example, lice such as the cattle louse (Haematopinus eurysternus), horse louse (Haematopinus asini), sheep louse (Dalmalinia ovis), cow louse (Linognathus vituli), pig louse (Haematopinus suis), pubic louse (Phthirus pubis), and head louse (Pediculuscapitis); chewing lice such as the dog louse (Trichodectes canis); and blood-sucking diptera pests such as the horsefly (Tabanus trigonus), the Japanese gnat (Culicoides schultzei), and the black fly (Simulium ornatum). Other examples of endoparasites include nematodes such as lungworms, mites, nodular worms, gastric parasites, roundworms, and filarial worms; tapeworms such as Diphyllobothrium mansoni, Diphyllobothrium latum, Dipylidium caninum, Dipylidium multicephalum, Dipylidium lamellarum, and Dipylidium multilocularis; trematodes such as Schistosoma japonicum and Liver fluke; and protozoa such as Coccidia, malaria parasites, Sarcoma intestinalis, Toxoplasma, and Cryptosporidium.

[0043] The pest control agent (for example, an agricultural and horticultural pest control agent) containing the crystals of the present invention as an active ingredient has a remarkable control effect against the aforementioned pests that damage paddy field crops, field crops, fruit trees, vegetables, other crops, and flowers. Therefore, the intended effect of the agricultural and horticultural pest control agent of the present invention can be achieved by treating seedling facilities, paddy fields, fields, seeds of fruit trees, vegetables, other crops, flowers, etc., paddy field water, stems and leaves, or soil, etc., before or after the occurrence of pests is confirmed, in accordance with the time when the occurrence of pests is predicted. Furthermore, it can also be used in a form that utilizes so-called systemic properties, by treating the soil used for raising seedlings of crops and flowers, the soil in planting holes during transplanting, the base of plants, irrigation water, cultivation water in hydroponics, etc., and allowing the compound of the present invention to be absorbed by the roots, with or without the soil.

[0044] The useful plants on which the pest control agent of the present invention (e.g., pest control agent for agricultural and horticultural use) can be used are not particularly limited, but include, for example, grains (e.g., rice, barley, wheat, rye, oats, corn, etc.), legumes (soybeans, adzuki beans, broad beans, peas, green beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leafy and fruiting vegetables (cabbage, tomatoes, spinach, broccoli, lettuce, onions, leeks (chives, scallions), bell peppers, eggplants, strawberries, peppers, okra, chives, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, radishes, turnips, lotus roots, burdock, etc.). Examples of plants include garlic, shallots, etc.), processing crops (cotton, hemp, beets, hops, sugarcane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), gourds (pumpkins, cucumbers, watermelons, cantaloupes, melons, etc.), pasture grasses (orchardgrass, sorghum, timothy, clover, alfalfa, etc.), turfgrasses (Korean grass, bentgrass, etc.), ornamental crops such as lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemums, roses, carnations, orchids, tulips, lilies, etc.), garden trees (ginkgo, cherry trees, Japanese laurel, etc.), and forest trees (fir trees, spruce trees, pine trees, cypress, cedar, hinoki, eucalyptus, etc.).

[0045] The above-mentioned useful plants include plants that have been conferred resistance to HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, acetyl-CoA carboxylase inhibitors such as cethoxydim, and herbicides such as bromoxynil, dicamba, and 2,4-D through classical breeding methods or genetic modification technology.

[0046] Examples of useful plants that have been given resistance through classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone-based ALS inhibitor herbicides such as imazetapyr, and are already sold under the trade name Clearfield (registered trademark). Similarly, there are soybeans that are resistant to sulfonylurea-based ALS inhibitor herbicides such as thifensulfuron-methyl through classical breeding methods, and 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 through classical breeding methods include SR corn.

[0047] Furthermore, plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors are described in the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), Vol. 87, pp. 7175-7179 (1990), among other publications. Furthermore, mutant acetyl-CoA carboxylase resistant to acetyl-CoA carboxylase inhibitors has been reported in Weed Science, Vol. 53, pp. 728-746 (2005), etc. By introducing such mutant acetyl-CoA carboxylase genes into plants using genetic engineering technology, or by introducing mutations related to resistance conferral into plant acetyl-CoA carboxylase, it is possible to create plants resistant to acetyl-CoA carboxylase inhibitors. In addition, chimeric plasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science) is also being considered. By introducing site-directed amino acid substitution mutations into plant cells using nucleic acids with base substitution mutations, such as those represented in 285:316-318, it is possible to create plants resistant to acetyl-CoA carboxylase inhibitors and ALS inhibitors, and the pest control agents of the present invention (for example, pest control agents for agricultural and horticultural use) can be used on these plants as well.

[0048] Furthermore, toxins expressed in genetically modified plants include: insecticidal proteins derived from Bacillus cereus and Bacillus popillie; δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis; insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion venom, spider venom, wasp venom or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; aglutinin; trypsin inhibitors, serine protease inhibitors, patatin, cystatin Examples include protease inhibitors such as papain inhibitors; ribosome inactivating proteins (RIPs) such as lysine, maize-RIP, abrin, rufin, saporin, and briodin; 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 receptors; stilbenzyl synthase; bibenzyl synthase; chitinase; and glucanase.

[0049] Furthermore, toxins expressed in such genetically modified plants include hybrid toxins of δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, and insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A, as well as toxins with partial deletions and modified toxins. Hybrid toxins are created using recombinant technology by novel combinations of different domains of these proteins. Among toxins with partial deletions, Cry1Ab, which has a partial deletion in its amino acid sequence, is known. Modified toxins have one or more amino acids substituted in the naturally occurring toxin. Examples of these toxins and recombinant plants capable of synthesizing them are described in EP0374753, WO93 / 07278, WO95 / 34656, EP0427529, EP0451878, WO03 / 052073, etc.

[0050] The toxins contained in these genetically modified plants confer resistance to various insects, particularly beetle pests, hemipteran pests, dipteran pests, lepidopteran pests, and nematodes. The pest control agents of the present invention (e.g., pest control agents for agricultural and horticultural use) can also be used in combination with or as part of these technologies.

[0051] The pest control agent of the present invention (for example, a pest control agent for agricultural and horticultural use) can be used as is, or diluted or suspended with water, in an amount effective for pest control, on the target (for example, plants) where the pest is expected to occur. For example, for pests that occur in fruit trees, grains, vegetables, etc., in addition to spraying on the stems and leaves, it can also be used by treating the soil, etc., such as by soaking seeds in the agent, coating seeds with powder, or treating with Calper, or by mixing it into the entire soil layer, applying it in furrows, mixing it into the bedding soil, treating cell seedlings, treating planting holes, treating the base of plants, top dressing, treating rice boxes, or applying it to the water surface, so that it can be absorbed by the roots. In addition, it can also be used by applying it to nutrient solutions in hydroponic cultivation, or by fumigation or injection into tree trunks.

[0052] Furthermore, the pest control agent of the present invention (for example, a pest control agent for agricultural and horticultural use) can be used as is, or diluted appropriately with water or the like, or suspended in an amount effective for pest control in places where the occurrence of the pest is expected. For example, it can be sprayed on stored grain pests, household pests, sanitary pests, forest pests, etc., and can also be used as a coating on building materials, a fumigation agent, a bait, etc.

[0053] Methods of seed treatment include, for example, immersing seeds in a liquid or solid formulation (either diluted or undiluted) to allow the agent to penetrate; mixing a solid or liquid formulation with the seeds, coating them with a powder to adhere to the surface; coating the seeds with an adhesive carrier such as a resin or polymer; and scattering the agent near the seeds at the same time as planting. The "seeds" to be treated in this manner refer to plant bodies in the early stages of cultivation used for plant propagation, and include, for example, seeds, bulbs, tubers, seed potatoes, buds, bulbils, or plant bodies used for vegetative propagation by cuttings.

[0054] When implementing the method of use of the present invention, the "soil" or "cultivation support" for plants refers to a support for cultivating crops, particularly a support for root growth. The material is not particularly limited, but any material on which plants can grow is acceptable, and may be so-called soil, seedling mats, water, etc. Specific materials may include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, polymer substances, rock wool, glass wool, wood chips, bark, etc.

[0055] Methods of application to crop stems and leaves or to stored grain pests, household pests, sanitary pests, or forest pests include diluting liquid formulations such as emulsions and flowable formulations, or solid formulations such as wettable powders or granular wettable powders with water and spraying them, spraying powders, or fumigation. Methods of application to soil include, for example, applying liquid formulations diluted with water or undiluted to the base of plants or seedling beds, scattering granules to the base of plants or seedling beds, scattering powders, wettable powders, granular wettable powders, or granules before sowing or transplanting and mixing them with the entire soil, or scattering powders, wettable powders, granular wettable powders, or granules to planting holes, furrows, etc. before sowing or planting plants.

[0056] For application to rice seedling trays, the formulation may vary depending on the application timing, such as application at sowing, greening, or transplanting, but it is acceptable to apply it in powder, wettable granule, or granular form. It can also be applied by mixing with the growing medium, such as mixing the growing medium with the powder, wettable granule, or granules, for example, mixing with the seedbed soil, covering soil, or mixing into the entire growing medium. Alternatively, the growing medium and various formulations can be applied in alternating layers. For application to paddy fields, solid formulations such as jumbo formulations, pack formulations, granules, and wettable granules, as well as liquid formulations such as flowable and emulsion formulations, are usually scattered onto flooded paddy fields. In addition, at the time of rice planting, a suitable formulation can be applied directly or mixed with fertilizer and scattered or injected into the soil. Furthermore, by using liquid formulations such as emulsions or flowables at the water inflow points into the paddy field, such as water inlets or irrigation systems, application can be carried out in a labor-saving manner in conjunction with the water supply.

[0057] For field crops, the treatment can be applied to the seeds or cultivation carriers near the plant body during the sowing and seedling stages. For plants sown directly in the field, in addition to direct application to the seeds, application to the base of the plants during cultivation is also preferable. The treatment can be applied by spraying granules or by drenching with the liquid agent, either diluted in water or undiluted. Mixing the granules with the cultivation carrier before sowing is also a preferred treatment. For plants to be transplanted, in addition to direct application to the seeds, drenching with the liquid agent or spraying with granules on the seedling bed is preferred. Furthermore, applying the granules to the planting hole at the time of transplanting or mixing them with the cultivation carrier near the transplanting site is also a preferred treatment.

[0058] The pest control agent of the present invention (for example, a pest control agent for agricultural and horticultural use) is generally used in a form convenient for use, in accordance with the conventional methods for formulating agricultural chemicals. That is, the B-type crystals of compound (1) of the present invention can be dissolved, separated, suspended, mixed, impregnated, adsorbed, or attached to a suitable inert carrier, or together with auxiliary agents in appropriate proportions as needed, and then formulated into an appropriate dosage form, such as a suspension, emulsion, liquid, wettable powder, granular wettable powder, granules, powder, tablet, pack, etc., for use.

[0059] The pest control agent of the present invention (for example, a pest control agent for agricultural and horticultural use) may contain, in addition to the active ingredient, additive components commonly used in agricultural chemical formulations as needed. Examples of such additive components include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, adsorbents, antifreeze agents, anticaking agents, disintegrants, and decomposition inhibitors. In addition, preservatives, plant fragments, etc., may be used as additive components as needed. These additive components may be used individually or in combination of two or more.

[0060] 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 husk, corn cob, tobacco stalk, etc.); 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 individually or in combination of two or more.

[0061] 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; and n-paraffin, na Examples include aliphatic hydrocarbons such as phthenes, isoparaffins, kerosene, and mineral oil; aromatic 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 dimethyl sulfoxide; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil; and water. These may be used individually or in combination of two or more.

[0062] 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 condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene block copolymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzylphenyl ether, polyoxyalkylene styrylphenyl ether, acetylenediol, polyoxyalkylene-added acetylenediol, polyoxyethylene ether-type silicone, ester-type silicone, and fluorine. Nonionic surfactants such as polyoxyethylene castor oil and hydrogenated polyoxyethylene castor oil; alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates, polyoxyethylene styrylphenyl ether sulfates, alkylbenzene sulfonates, alkylaryl sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkylnaphthalene sulfonic acid, fatty acid salts, polycarboxylates, polyacrylates, N-methyl fatty acid sarcosinates, resin salts, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkylphenyl ether phosphates; cationic surfactants such as alkylamine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, and alkyldimethylbenzalkonium chloride;Examples include amphoteric surfactants such as amino acid-type or betaine-type surfactants. These surfactants may be used individually or in combination of two or more types.

[0063] 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 with an average molecular weight of 6,000 to 20,000, polyethylene oxide with 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 made of polyhydric alcohols and dicarboxylic acid anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffin, terpenes, polyamide resins, polyacrylates, polyoxyethylene, waxes, polyvinyl alkyl ethers, alkylphenol formalin condensates, and synthetic resin emulsions.

[0064] Examples of thickening agents include water-soluble polymers such as xanthan gum, guar gum, tung 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).

[0065] Examples of colorants include inorganic pigments such as iron oxide, titanium dioxide, and Prussian blue, as well as organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.

[0066] Examples of antifreeze agents include ethylene glycol, diethylene glycol, propylene glycol, and polyhydric alcohols such as glycerin.

[0067] Examples of auxiliary agents 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 stearate, cellulose powder, dextrin, copolymers of methacrylate esters, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers, and starch-polyacrylonitrile graft copolymers.

[0068] Examples of decomposition inhibitors 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.

[0069] Examples of preservatives include potassium sorbate and 1,2-benzothiazolin-3-one. Furthermore, if necessary, functional spreading agents, activity enhancers such as metabolic degradation inhibitors like piperonyl butoxide, antifreezes such as propylene glycol, antioxidants such as BHT, and other auxiliary agents such as UV absorbers may also be used.

[0070] The proportion of the active ingredient compound can be adjusted as needed. It can be appropriately selected and used in an amount ranging from 0.01 to 90 parts by mass per 100 parts by mass of the pest control agent of the present invention (e.g., pest control agent for agricultural and horticultural use). For example, when using a powder, granules, emulsion, or wettable powder, 0.01 to 50 parts by mass [0.01 to 50% by mass relative to the total mass of the pest control agent (e.g., pest control agent for agricultural and horticultural use)] is appropriate.

[0071] The amount of the pest control agent of the present invention (for example, a pest control agent for agricultural and horticultural use) used will vary depending on various factors such as purpose, target pest, crop growth status, pest occurrence trend, weather, environmental conditions, formulation, application method, application location, and application timing. However, the amount of the active ingredient compound can be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 ares, depending on the purpose.

[0072] The pest control agent of the present invention (for example, a pest control agent for agricultural and horticultural use) can be used in combination with other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, biological pesticides, etc., in order to expand the range of pests and diseases that can be controlled, the optimal timing for control, or to reduce the amount of chemicals used. It can also be used in combination with herbicides, plant growth regulators, fertilizers, etc., depending on the application.

[0073] Other agricultural and horticultural insecticides, acaricides, and nematicides used for this purpose 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 acynonapyr. Azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, aldrin drin), alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isoamidofos, isoxathion, isocycloseram, isofenphos, isoflualanam, isoprocarb (MIPC), epsilon-metofluthrin,Epsilon-momfluorothrin, ivermectin, imicyafos, imidacloprid, imiprothrin, indazapyoxamet, indoxacarb, vadescana, esfenvalerate, ethiofencarb, ethion, ethiprole, etoxazole, etofenprox hofenprox), etoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfendazole, potassium oleate oleate), sodium oleate, cadusaphos, kappa-bifenthrin, cartap, carbaryl, carbosulfan, carbofuryl, gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionate, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole,Chlorethoxyfos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, kelthane (dicofol): Diclofenthion (dichl), salition, cyanophos (CYAP), diafenthiuron, diamidaphos, cyantraniliprole, theta-cypermethrin, cyetpyrafen, dienochlor, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, diclofenthion (dichl) ofenthion (ECP), cyclobutrifluram, cycloprothrin, dichlorvos (DDVP), dichloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofen, cyproflanilide, diflovidazin,Cyhexatin, Cypermethrin, Dimethylvinphos, Dimethoate, Dimpropyridaz, Cybenzoxasulfyl, Dimefluthrin, Silafluofen, Cyromazine, Spidoxamat, Spinetram oram), spinosad, spirodiclofen, spirotetramat, spirobudifen, spiropidion, spiromesifen, sulfiflumin, sulfindoflufen, sulfluramid, sulprofos, sulfoxaf Sulfoxaflor, sulfoxamyl, zeta-cypermethrin, diazinon, tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, tiapyrachlor, tioxazafen, thiodicarb, thia Ocyclam, thiosultap, thiosultap-sodium, thionazin, thiometon, thiorantraniliprole, 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, trioxyflanilide, trichlamide, trichlorphon (DEP), trifluenfuronate, triflumezopyrium, triflumuron, tolfenpyrad, naled: BRP), nicofluprole, nithiazine, nitenpyram, novaluron, nobiflumulon, hydroprene, vaniliprole, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, pioxaniliprole, bistrifluron, bisultap, bisulflufen, hydramethylnon, hydroxypropyl starch,Binapacryl, vinylfluthrin, pyflubumide, bifenazate, bifemetstrobin, bifenthrin, piperflanilide, pymetrozine, pyraclorfos, pyrafluprole, pyridafenthion, pyridaben (pyridaben), pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins, fipronil, fenazaquin, fena Fenamiphos, fenargimine, phenisobromolate, fenitrothion (MEP), fenoxycarb, fenothiocarb, phenothrin, fensulfothion, fentiazoluron, fenthion (MPP), phenthoate (PAP) ), fenvalerate, fenpyroximate, fenpropathrin, fenbendazole, fenmezoditiaz, fosthiazate, formetanate, butathiofos, buprofezin, furathiocarb, prallethrin,Fluacrypyrim, fluazaindolizine, fluazinam, fluazuron, fluensulfone, fluxametamide, fluchlordiniliprole, flucycloxuron, flucythrinate, fluvalinate, flupimezothiaz (fl upymezotiaz), flupyradifurone, flufiprole, flupyrazofos, flupyrimin, flupyroxystrobin, flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenoprox, Fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flupentiofenox, flumetnicam, flumethrin, flurimfen, prothiofos, protrifenbute, flonicamid, propafo Propaphos, propargite (BPPS), profenofos, broflanilide, profluthrin, propoxur (PHC), flometoquin, alpha-bromadiolone, bromopropylate, beta-cyfluthrin, hexaflumuron,Hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiaz, bendiocarb, bentiocarb, bentiolumin, 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, metamidophos, metam-ammonium, metam-sodium, methiocarb (methiocarb), methidathion (DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, metoxadiazone, methoxychlor, methoxyfenozide, metofluthrin, methoprene, metolcarb,Meperfluthrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin, ryanodine, lufenuron, rescalure, resmethrin, ledprona, lepimectin, rotenone, levamisol hydrochloride, fenbutatin oxide, morantel tartarate, methyl bromide, tricyclohexyl tin hydroxide, calcium cyanamide, calcium sulfur mixture Examples include polysulfide, sulfur, and nicotine sulfate, or salts thereof.

[0074] Examples of compounds with bactericidal activity (bactericides) include aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, aminotipyr, aminopyrifen, ampropylfos, ametoctradin, and allyl alcohol. alcohol), aldimorph, amobam, isotianil, isovaledione, isopyrazam, isofetamide, isoflucypram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine iminoctadine, iminoctadine albesilate, iminoctadine triacetate, imibenconazole, inpyrfluxam, uniconazole, uniconazole-P, eclomezole, edifenphos, etaconazole, etaboxam, ethirimol, etem, ethoxyquin, etridiazole,Enestrobrin, enoxastrobin, epoxyconazole, enprocymid, oxadixyl, oxathiapiprolin, oxycarboxin, copper-8-quinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate, oxolinic acid Acid, octhilinone, ofurace, orysastrobin, metam-sodium, kasugamycin, galquin, carmeconazole, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamide, quinacetol, quinaminoprole, quinoxyfen, quinofumerine Lin), chinomethionate (quinomethionate), captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine, cufraneb, cuprobam, coumoxystrobin, glyodin, griseofulvin, climbazole, cresol, kresoxim-methyl, chlozolinate,Clotrimazole, clobenthiazone, chloraniformethan, chloranil, chlorquinox, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, chloroneb, salicylanilide, zarilamid, cyazofamid, diethyl pyroppacarbonate pyrocarbonate, diethofencarb, cyclafuramid, diclocymet, dichlozoline, cyclobunofen, diclobutrazol, dichlofluanid, cycloheximide, diclobentiazox, diclomezine, dichloran, dichlorophen, dichlone, disulfiram ), ditalimfos, dithianon, diniconazole, diniconazole-m, zineb, dinocap, dinocton, dinosulfon, dinoterbon, dinobuton, dinopenton, dipymetitrone, dipyrithione, diphenylamine, difenoconazole, cyflufenamid,Diflumetrim, cyproconazole, cyprodinil, cyprofuram, cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, seboctylamine, zoxamide, dazomet, thiadiazine iazin, tiadinil, thiadifluor, thiabendazole, tioxymid, thioquinox, thiochlorfenphim, thiophanate, thiophanate-methyl, thifluzamide, thicyofen, thioquinox, thiram, decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid acid), tebuconazole, tebufloquin, dodicin, dodine, bisethylenediamine copper complex (II) dodecylbenzenesulfonate (DBEDC), dodemorph, drazoxolon, triadimenol, triadimefon, triazbutyl,Triazoxide, triamiphos, triarimol, trichlamide, triclopyricarb, tricyclazole, triticonazole, tridemorph, tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb, natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, copper nonylphenol sulfonate sulfonate, halacrinate, validamycin, valifenalate, harpin protein protein), picarbutrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroisoxazole-potassium, binapacryl, biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyraziflumid, pyrazophos,Pyrapropoyne, pyrametostrobin, pyriophenone, pyridinitril, pyridflumetofen, pyrisoxazole, pyridaclomethyl, pyrifenox, pyribencarb, pyriminostrobin, pyrimethanil (pyr imethanil, pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, ferbam, famoxadone, fenapanil, fenamidone, fenaminosulf, fenaminstrobin, fenarimol, fenitropan ), fenoxanil, feneptamidoquin, fenopyramid, ferimzone, ferbam, fentin, fenpiclonil, fenpicoxamide, fenpyrazamine, fenbuconazole, fenfuram, fenpropidine n) fenpropimorph, fenhexamide, phthalide, butthiobate, butylamine, bupirimate, fuberidazole, blasticidin-s, furametpyr, furalaxyl, fluacrypyrim, fluazinam,Fluindapyr, fluoxastrobin, fluoxapiprolin, fluoxytioconazole, fluotrimazole, fluopicolide, fluopimomide, fluopyram, fluoroimide, furcarbanil, fl uxapyroxad), fluquinconazole, furconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, flufenoxadiazam, flufenox flufenoxystrobin, furfural, flubeneteram, furmecyclox, flumetylsulforiim, flumetover, flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole thioconazole), pronitridine, propamocarb, propiconazole, propineb, furophanate, probenazole, bromuconazole, florylpicoxamid, hexachlorobutadiene, hexaconazole,Hexylthiofos, bethoxazin, benalaxyl, benalaxyl-m, benodanil, benomyl, pefurazoate, benquinox, penconazole, benzamorf, pencycuron, benzohydroxamic acid 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, metazoxolon, metam, metam-sodium, metalaxyl, metalaxyl-m, metarylpicoxamid, metiram, methyl isothiocyanate,Meptyldinocap, methyltetraprole, metcyclofenstrobin, metconazole, metsulfovax, metofloxam, metominostrobin, metrafenone, mepanipyrim, mefenoxam, mefentrifluconazole, meptyldinocap, mepronil, mebenil, iodomethane, rabenzazole, methyl bromide, benzalkonium chloride, basic copper chloride, basic copper sulfate Examples include inorganic disinfectants such as sulfate and metallic silver, sodium hypochlorite, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, inorganic sulfur, anhydrous copper sulfate anhydride, nickel dimethyldithiocarbamate, copper compounds such as 8-hydroxyquinoline copper, zinc sulfate, and copper sulfate pentahydrate, or salts thereof.

[0075] Examples of compounds with herbicidal activity (herbicides) and plant growth regulators 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, icafolin, and Acroni. Aclonifen, azaphenidin, acifluorfen, aziprotryne, azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, abiglycine, abscisic acid acid), amicarbazone, amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor, alloxydim, allo Alorac, Iofensulfuron, Isouron, Isocarbamid, Isoxachlortole, Isoxapyrifop, Isoxafenacil, Isoxaflutole, Isoxaben, Isocil, Isonoruron, Isoproturon, Isopropalin,Isopolinate, isomethiozin, inabenfide, ipazine, iptriazopyrid, ipfencarbazone, iprymidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazametabenz Methabenz, imazametabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolauxipyr, indolauxipyr-cyanomethyl, indolebutyric acid acid), uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron-methyl, ethalfluralin, ethiolate, etychlozate, ethidimuron, etinofen, etephon, ethoxysulfuron lfuron), ethoxyfen, etnipromid, ethofumesate, etobenzanid, epirifenacil, epronaz, erbon, endothal, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron, oxapyrazon,Oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, cafenstrole, cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, carbutilate, carbeta mide), carboxazole, quizalofop, quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron, clacyfos, cliodinate, glyc Glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop, clodinafop-propargyl, chlorotoluron, clopyralid, cloproxydim, cloprop op), chlorbromuron, clofop, clomazone, chlomethoxynil, chlomethoxyfen, clomeprop, chlorazifop, chlorazine, cloransulam, chloranocryl, chloramben, cloransulam,Chloransulam-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlortoluron, chlornitrofen, chlorfenac, chlorfenprop, chlorbufam, chlorphthalim, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil, chloroxuron, chlorotoluro n) chloropon, cypyrafluone, saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat, dioxopyritrione, dicamba, cycluron, cycloate, cyclooxydim, diclo Diclosulam, cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlorprop, dichlorprop-P, diclobenil, diclobenz-methyl, diclofop, diclofop-methyl, dichlormate,Dichloralurea, Diquat, Cisanilide, Disul, Siduron, Dithiopyr, Dinitramine, Cinidon-ethyl, Dinosam, Cinosulfuron, Dinoseb, Dinoterb, Dinophenate, Dinoprop, Cyhalopho Cyhalofop-butyl, diphenamid, difenoxuron, difenopenten, difenzoquat, cybutryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperco Cyperquat, gibberellin, simazine, dimexano, dimesulfazet, dimethachlor, dimidazon, dimethametryn, dimethenamid, simetryn, simeton, dimepiperate, dimepyrolimet, dimeflon (dimefuron), cinflubrolin, cinmethylin, swep, sulglycapin, sulcotrione, sulffallate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton,Setoxydim, sebuthylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr, tiafenacil, thiencarbazone, thiencarbazone-methyl, tiocarbazil, thio Tioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet, tetrafluron, thenylchlor ), tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delachlor, terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, toxapizone ( toxapyzone, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone, tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron,Tripyrasulfone, trifludimoxazin, triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, trippropindan, tribenuron, tribenuron-methyl, triphop (tr iFOP, trifopsime, trimeturon, tolpyralate, naptalam, naproanilide, nappropamide, nicosulfuron, nitralin, nitrofen, nitrofluorfen, nipyraclofen, neburon, norflurazone (norflurazon), noruron, barban, paclobutrazol, paraquat, parafluron, haloxydine, haloxifen, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron ), halosulfuron-methyl, bilanafos, bixlozone, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, pydanon, pinoxaden, bipyrazone, bifenox,Piperophos, hymexazol, pyraquinate, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, bilanafos, pyrafulfen ethyl (py Pyrifluben-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyriflubenzoxim, pyribenzoxim, pyrimisulfan fan), primisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop Phenothiol, fenoprop, phenobenzuron, feproxydim, fenquinotrione, fendioxypyracil, fenthiaprop, fenteracol, fentrazamide, phenmedipham, phenmedipham-ethyl,Fenpyrazone, butachlor, butafenacil, butamifos, buthiuron, buthidazole, butyrate, buturon, butenachlor, butoxydim, butralin, butroxydim, flazasulfuron, flampro Flamprop, furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop-butyl, fluazolate, fluchloraminopyr, fluchloraminopyr-tefuryl, fluochi fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium, fluquinometoate, fluchlora Phosphorus (fluchloralin), flusulfinam, flucetosulfuron, fluthiacet, fluthiacet-methyl, flupyrsulfuron, flufenauxirim, flufenauxirim-metotyl, flufenacet, flufenazopyr,Flufenican, flufenoximacil, flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn, flumezin, flumethoslam (f Lumetsulam, fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proglinazine, broclozone, prochlorosulfone, procyazine, prodiamine, prosulfalin, prosulfuron ron), prosulfocarb, propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin luralin, prohexadione-calcium, propoxycarbazone, propoxycarbazone-sodium, profoxydim, bromacil, brompyrazon, prometryn, prometon, bromoxynil, bromofenoximBromobutide, bromobonil, florasulam, florpyrauxifen, hexachloroacetone, hexazinone, petoxamide, benazolin, penoxsulam, pebulate, beflubutamide, beflubutamide-M, vernolate, perfluidone, bencarbazone, benquitrione, benzadox, benzipram, benzylaminopurine, benzthi azuron), benzfendizone, bensulide, bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleate hydrazide hydrazide), mecoprop, mecoprop-P, medinoterb, mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprazine,Mesoprotryne, metazachlor, methazole, metazosulfuron, metabenzthiazuron, metamitron, metamifop, metam, metalpropalin, methiuron, methiozolin, methiobencarb, methyldymron, metoxuron, metosulam, metosulfuron n) Methosulfuron-methyl, metoflazon, metproxybicyclone, metobromuron, metobenzuron, methometon, metolachlor, metribuzin, mepiquat-chloride, mefenacet, mefluidide, monalide, monisouron, monuron, monochloroacetic acid acid), monolinuron, molinate, morfamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, lancotrione, rimisoxafen, linuron, rimsulfuron, lenacil, rhodethanil, calcium peroxide,Examples include methyl bromide, or salts thereof.

[0076] Examples of biopesticides include Agrobacterium radiobacter (e.g., Galltrol-A (registered trademark) from AgBioChem, CA using strain K84, and Nogall (registered trademark) from Becker Underwood, US using strain K1026), Agrobacterium radiobacter (e.g., Bacterose (registered trademark) from Nippon Soda Co., Ltd. using strain 84), Ampelomyces quisqualis (e.g., AQ10 (registered trademark) from IntrachemBio Italia & Co. KG using strain AQ10), and Aspergillus flavus (e.g., Afla-Guard (registered trademark) from Syngenta, and Arizona Cotton Research and Protection using strain AF36). Examples of products containing fertilizers include "AF36 (registered trademark)" from Council, US, "Afla-Guard" from Syngenta using NRRL 21882, Aureobasidium pullulans (for example, "Botector (registered trademark)" from bio-ferm, GmbH, which is a mixture of budding spores from strain DSM14940 and strain DSM14941), Bacillus amyloliquefaciens (for example, "Impression Clear (registered trademark)" from Idemitsu Agri Co., Ltd. using strain AT-332, and "Avogreen (registered trademark)" from University of Pretoria using strain B246), and strain D747 (for example, "Bacstar (registered trademark)" from Etec Crop Solutions, NZ, and "Dagutat" using strain DB101). "Shelter®" manufactured by Biolab, ZA; "Artemis®" manufactured by Dagutat Bio lab, ZA using strain DB102; "RhizoVital®" manufactured by ABiTEP, DE using strain FZB42; and "Bayer Crop" using strain GB03."Kodiak®" manufactured by Science AG, DE, "Subtilex®" manufactured by Becker Underwood, US using strain MBI600, "Amplitude" manufactured by Marrone Bio Innovations, Inc. using strain F727, Bacillus cepacia (e.g., "Deny Stine®" manufactured by Microbial Products), Bacillus cereus (e.g., "Mepichlor®" manufactured by Arysta, US using strain BP01), Bacillus firmus (e.g., "BioNeem®" manufactured by AgoGreen using strain I-1582), Bacillus lacticola (e.g., manufactured by Micro Flo Company), Bacillus lactimorbus (e.g., manufactured by Micro Flo Company) Bacillus lactis (e.g., manufactured by Micro Flo Company), Bacillus laterosporus (e.g., Bio-Tode® manufactured by Agro-Organics, SA), Bacillus licheniformis (e.g., EcoGuard Biofungicide® manufactured by Novozymes using strain SB3086), Bacillus maroccanus (e.g., manufactured by Micro Flo Company), Bacillus megaterium (e.g., Bioarc® manufactured by Bio Arc using strain YFM3.25), Bacillus metiens (e.g., manufactured by Micro Flo Company), Bacillus mojavensis (Bacillus mojavensis) (for example, "Probelte, Sa" using strain SR11), Bacillus mycoides (Bacillusmycoides) (for example, "BmJ®" manufactured by "Certis USA" using isolate J.), Bacillus nigrificans (for example, manufactured by "Micro Flo Company"), Bacillus popilliae (for example, "Cronox®" manufactured by "Bio Crop, CO"), Bacillus pumilus (for example, "Integral F-33®" manufactured by "Becker Underwood, US" using strain BUF-33, "Yield Shield®" manufactured by "Bayer Crop Science AG, DE" using strain GB34, and "Bayer Crop Science" using strain QST2808) "Sonata®" manufactured by LP, US; Bacillus simplex (e.g., "Momihope Wettable Powder®" manufactured by Arista LifeSciences, Inc. using strain CGF2856); Bacillus sphaericus (e.g., "VectoLex®" manufactured by Valent BioSciences, US using antigen type H5a5b strain 2362); Bacillus subtilis (e.g., "Botkiller Wettable Powder®" manufactured by Idemitsu Agri Co., Ltd., "Taegro®" manufactured by Novozyme Biologicals, Inc. US using strain FZB24, and "SERENADE" manufactured by Bayer CropScienceLP, US using strain QST713 / AQ713) "MAX (registered trademark)", "Serenade-DPZ (registered trademark)" using AQ30002, "Eco Shot (registered trademark)" manufactured by Kumiai Chemical Co., Ltd. using D747, "Agrocare Wettable Powder (registered trademark)" manufactured by Nisso Green Co., Ltd. using HAI-0404, "Botpica Wettable Powder (registered trademark)" manufactured by Idemitsu Kosan Co., Ltd. using MBI600, "Batistar Wettable Powder (registered trademark)" manufactured by Arista Life Sciences Inc. using Y1336, and "Companion Biological" manufactured by Growth Products Ltd. using GB03Fungicide Wettable Powder), Bacillus thuringiensis (e.g., "VectoBac®" from Valent BioSciences, US using strain AM65-52), Bacillus thuringienses aizawai (e.g., "XenTari®" from Bayer Crop Science AG, DE using strain ABTS-1857, "Florbac WG®" from Valent BioSciences, US using antigen type H-7, and "Agree WG Biological Insecticide" from Certis USA using strain GC-91), Bacillus thuringiensis subspecies. Aegypti) (e.g., "Agerin®"), Bacillus thuringienses israelensis (e.g., "Aquabac®" manufactured by "Becker Microbial Products IL" using strain BMP144), Bacillus thuringienses kurstaki (e.g., "Dipel ES®" manufactured by "Becker Microbial Products, IL" using strain BMP 123, "BMP 123" manufactured by "Becker Microbial Products" using strain HD-1, "BMP 123" manufactured by "Becker Microbial Products" using strain BMP123, "BMP144 / Aquabac" manufactured by "Becker Microbial Products" using strain BMP144, "Dipel" manufactured by "Valent U.S.A. LLC." using strain ABTS-351) "10G", "Condor Wettable Powder" manufactured by "Certis USA" using strain EG2348, "Crymax Bioinsecticide" manufactured by "Certis USA" using strain EG7841, "Certis" using strain SA-12"Deliver Biological Insecticide" from the USA, "Bioprotec PLUS" from AEF Global using strain EVB-113-19), Bacillus thuringiensis galleriae (for example, "beetleGONE!" from Phyllom BioProducts, and "boreGONE!" from Phyllom BioProducts using strain SDS-502), Bacillus thuringiensis var. Colmeri (for example, "TianBaoBTc(registered trademark)" from Changzhou Jianghai Chemical Factory), Bacillus thuringienses tenebrionis (for example, "Novodor" from BioFa DE using strain NB176) FC (registered trademark)), Bacillus thuringiensis var. san diego (for example, "M-One (registered trademark)" made from "Bacillus thuringiensis var. san diego"), Beauveria bassiana (for example, "Naturalis (registered trademark)" made by "Intrachem Bio Italia", "Bove Max (registered trademark)" made by "Novozymes" using strain CG716, "Biolisa Madara (registered trademark)" made by "Idemitsu Kosan Co., Ltd." using strain F-263, "BotaniGard Wettable Powder (registered trademark)" made by "ARYSTA" using strain GHA, "balEnce" made by "Terragena, Inc." using strain HF23, "BotaniGard ES" made by "BioWorks Inc." using strain GHA, "BioCeres" made by "BioSafe Systems" using strain ANT-03) WP), Beauveria brongniartii (for example, "Andermatt Biocontrol")AG's "Beaupro(registered trademark)", Bradyrhizobium japonicum (e.g., Novozymes' "Optimize(registered trademark)"), Burkholderia spp. (e.g., Marrone Bio Innovations' "MBI-206 TGAI(registered trademark)" using strain A396), Candida oleophila (e.g., Ecogen Inc., US's "Aspire(registered trademark)" using strain I-82, and BioNext's "Nexy(registered trademark)" using strain O), Candida saitoana (e.g., Micro Flo Company, US (BASF SE)'s "BIOCURE(registered trademark)"), Chaetomium cupreum (e.g., AgriLife's "BIOKUPRUM TM (registered trademark)), Chaetomium globosum (e.g., "Rivadiom (registered trademark)" manufactured by "Rivale"), Chromobacterium subtsugae (e.g., "Grandevo (registered trademark)" manufactured by "Marrone Bio Innovations" using strain PRAA4-1T), Cladosporium cladosporioides (e.g., manufactured by "Cladosporium cladosporioides"), Clonostachys rosea f. catenulate (e.g., "PRESTOP (registered trademark)" manufactured by "Verdera, Finland" using strain J1446), Colletotrichum gloeosporioides (e.g., manufactured by "Agriultural Research") "Collego®" manufactured by "Initiatives", Coniothyrium minitans (for example, using strain CON / M / 91-08)Contans® (manufactured by Technologies, LLC), Cryptococcus albidus (e.g., YieldPlus® (manufactured by Anchor Bio Technologies, ZA)), Delftia acidovorans (e.g., BioBoost® (manufactured by Brett Young Seeds) using strain RAY209), Dilophosphora alopecuri (e.g., Twist Fungus®), Drecsrela monoceras (e.g., Tasmart Herbicide® (manufactured by Mitsui Chemicals Agro, Inc.) using strain MTB-951), Entomophthora virlenta Virulenta) (e.g., "Vektor®" manufactured by "Ecomic"), Fusarium oxysporum (e.g., "Marukalite" manufactured by "Eisai Bio-tech Research Co., Ltd." using strain 101-2), Fusarium oxysporum (e.g., "Fusaclean®" manufactured by "Natural Plant Protection" using strain Fo47), Gliocladium spp. (e.g., "Prestop®" manufactured by "AgBio Inc." using strain J1446, and manufactured by "W.F. Stoneman Company LLC" using strain 321U), Hirsutella thompsonii (e.g., "Mycohit®" manufactured by "Agro Bio tech Research Centre, IN"), Lactobacillus acidophilus acidophilus) (for example, "Fruitsan®" manufactured by "Inagrosa Industrias Agrobiologicas, S.A."), Lactobacillus plantarum (for example, "Meiji Seika" using strain BY)Pharma Co., Ltd.'s "LactGuard Wettable Powder", Lecanicillium lecanii (for example, "Mycotal®" manufactured by Koppert / Arysta using conidia of strain KV01), Metarhizium anisopliae (for example, "BIO 1020®" manufactured by Bayer CropScience using strain F52, "Pirates Granules®" manufactured by Arista LifeScience Co., Ltd. using strain SMZ-2000, and "Bio-Blast" manufactured by LidoChem Inc. using strain ESC1), Metarhizium anisopliae var. acridum (for example, "Green Muscle®" manufactured by Biological Control Products, and "Becker GreenGuard (registered trademark) manufactured by Underwood, US; Metschnikowia fructicola (e.g., Shemer (registered trademark) manufactured by Bayer CropScience); Microdochium dimerum (e.g., ANTIBOT (registered trademark) manufactured by Agrauxine, France); Microsphaeropsis ochracea (e.g., Microx (registered trademark) manufactured by Prophyta); Monacrosporium phymatopagum (e.g., Nemahiton (registered trademark) manufactured by Tomoe Chemical Industry Co., Ltd.); Mucor haemelis (e.g., BioAvard (registered trademark) manufactured by Indore Biotech Inputs & Research); Muscodor albus albus) (for example, "Arabesque" from Bayer Crop Science using strain QST 20799), Myrothecium verrucaria (for example, "Valent" using strain AARC-0255)"DiTera™" manufactured by Biosciences, Paecilomyces fumosoroseus (for example, "PreFeRal® WG" manufactured by Biobest using strain apopka 97, "Preferred Wettable Powder" manufactured by Tokai Bussan Co., Ltd., and "No Fly®" manufactured by Natural Industries Inc. (Novozymes company) using strain FE9901), Paecilomyces lilacinus (for example, "BioAct WG®" manufactured by Prophyta using strain 251), Paecilomyces tenuipes (for example, "Gottsu A®" manufactured by Idemitsu Kosan Co., Ltd. using strain T1), Paecilomyces bariothii Paenibacillus variotii (for example, "Nemaquim®" manufactured by "Quimia, MX" using strain Q-09), Paenibacillus polymyxa (for example, "Topseed®" manufactured by "Green Biotech Company Ltd." using strain AC-1), Paenibacillus poppiliae (for example, "Milky spore disease®" manufactured by "St. Gabriel Laboratories"), Pasteuria nishizawae (for example, "oyacystLF / ST®" manufactured by "Pasteuria Bioscience" and "Clariva pn" manufactured by "Syngenta" using strain Pn1), Pasteuria penetrans (for example, "Pasteuria Pasteuria® (manufactured by Bioscience), Pasteuria usagae (e.g., Econem® (manufactured by Pasteuria Bioscience)), Pantoea agglomerans (e.g., Bloomtime (manufactured by Nufarm US) using strain E325)Biological FD Biopesticide), Pectobacterium carotovorum (e.g., BioKeeper® manufactured by Nissan Chemical Corporation, and Ecomate® manufactured by Kumiai Chemical using strain CGE234M403), Phoma macrostroma (e.g., Phoma H® manufactured by Scotts, US using strain 94-44B), Penicillium bilaii (e.g., Jump Start® manufactured by Novozymes), Phlebiopsis gigantea (e.g., ROTSOP® manufactured by Verdera, Finland using strain FOC PG B22 / SP1190 / 3.2), Pochonia chlamydosporia catenulata Chlamydosporia var. catenulata (e.g., "KlamiC®" manufactured by "The National Center of Animal and Plant Health (CENSA); CU"), Pseudomonas aureofaciens (e.g., "Spot-Less Biofungicide®" manufactured by "Eco Soils Systems, CA" using strain TX-1), Pseudomonas chlororaphis (e.g., "ATEze®" manufactured by "EcoSoil Systems" using strain 63-28, and "Cedomon®" manufactured by "Bioagri, S" using strain MA342), Pseudomonas fluorescens (e.g., "Frostban" manufactured by "Frost Technology Corp" using strain 1629RS)D(registered trademark), "Blightban(registered trademark)" manufactured by "Blightban" using strain A506, "Small Seedling Soil(registered trademark)" manufactured by "Taki Chemical Co., Ltd." using strain FPT-9601, "Cell Seedling Genki(registered trademark)" manufactured by "Taki Chemical Co., Ltd." which is a mixture of strains FPT-9601 and FPH-9601, "Veggie Keeper(registered trademark)" manufactured by "Arista Life Science Co., Ltd." using strain G7090), Pseudomonas proradix (e.g., "Proradix(registered trademark)" manufactured by "Sourcon Padena"), Pseudomonas resinovorans (e.g., "Solanacure(registered trademark)" manufactured by "Agricultural Research Council, SA"), Pseudomonas syringae (Pseudomonas Pseudomonas spp. (e.g., Biosave® manufactured by EcoScience, US using strain MA-4, Frost Technology Corp® manufactured by Frostban C using strain 742RS, Bio-save 10LP Biological Fungicide manufactured by Jet Harvest Systems using strain ESC10, and Bio-Save 11 LP Biological Fungicide manufactured by Jet Harvest Systems using strain ESC11), Pseudomonas spp. (e.g., Masterpiece Wettable Powder® manufactured by Nippon Soda Co., Ltd. using strain HAI-0804, and Momigenki Wettable Powder manufactured by Nissan Chemical Industries, Ltd. using strain CAB-02), Pseudozyma aphidis (e.g., Yissum Research Development Company of the Hebrew University of (Manufactured by Jerusalem), Pseudozyma flocculosa (for example, "Sporodex L®" manufactured by Plant Products Co. Ltd, CA using strain PF-A22 UL), Pythium oligandiol* oligandrum* (e.g., "Polyversum®" manufactured by "Bioprepraty, CZ" using strain DV74 or M1), * Reynoutria sachlinensis* (e.g., "REGALIA®" manufactured by "Marrone BioInnovations, US"), * Rhizopogon amylopogon* (e.g., "Myco-Sol®" manufactured by "Helena Chemical Company"), * Rhizopogon fulvigleba* (e.g., "Myco-Sol®" manufactured by "Helena Chemical Company"), * Saccharomyces cerevisiae* (e.g., manufactured by "Lesaffre et Compagnie, FR"), * Sclerotinia minor* (e.g., "Agrium Advanced Sarritor (registered trademark) from Technologies, Serratia entomophila (e.g., Invade (registered trademark) from Wrightson Seeds), Sporothrix insectorum (e.g., Sporothrix Es (registered trademark) from Biocerto;BR), Steinernema carpocapsae (e.g., Biosafe (registered trademark) from SDS Biotech Co., Ltd.), Steinernema kushidai (e.g., Shibaichi Nema from Kubota Corporation), Steinernema glaseri (e.g., Biotopia (registered trademark) from Arista LifeScience Co., Ltd.), Streptomyces assisiscabies acidiscabies (for example, "MBI-005EP®" manufactured by "Marrone Bioinnovations, CA" using strain RL-110T), Streptomyces candidusStreptomyces candidus (e.g., BioBac® manufactured by Biotech, TW using strain Y21007-2), Streptomyces galbus (e.g., Mycostop® manufactured by Verdera using strain K61), Streptomyces lydicus (e.g., ACTINOVATE® manufactured by Natural Industries, US using strain WYEC108), Streptomyces saraceticus (e.g., Clanda® manufactured by A&A Group (Agro Chemical Corp.)), Talaromyces flavus flavus) (for example, "Momikeeper (registered trademark)" manufactured by "Central Glass Co., Ltd." using strain B-422, "Toughblock (registered trademark)" manufactured by "Idemitsu Kosan Co., Ltd." using strain SAY-Y-94-01, and "PROTUS (registered trademark) WG" manufactured by "Prophyta, DE" using strain V117b), Trichoderma asperellum (for example, "Isagro" using strain ICC 012, "T34 Biocontrol (registered trademark)" manufactured by "Bioncontrol Technologies, ES" using strain T34, and "ECO-HOPE (registered trademark)" manufactured by "Kumiai Chemical Industry Co., Ltd." using strain SKT-1), Trichoderma atroviride (for example, "Esquive (registered trademark) WP" manufactured by "Agrauxine, FR" and "Agrimm Technologies" using strain LC52) "Tenet®" or "SENTINEL®" manufactured by Ltd, NZ, "Ecohope DJ®" manufactured by Kumiai Chemical Industry Co., Ltd. using strain SKT-1), Trichoderma gamsii (e.g., "BIO-TAM™" manufactured by Bayer CropScienceLP, US), Trichoderma harzianum (e.g., "Dagutat" using strain DB103)"T-Gro 7456 (registered trademark)" from Biolab, "Trianum-P (registered trademark)" from Koppert using strain ITEM908, "Trichoplus (registered trademark)" from Biological Control Products, SA using strain KD, "ROOT PRO (registered trademark)" from Mycontrol Ltd. using strain TH-35), Trichoderma harzianum rifai (for example, "PLANTSHIELD T-22G (registered trademark)" from Firma BioWorks Inc. US using strain T-22, and "TRICHODEX (registered trademark)" from Makhteshim Ltd, US using strain T-39), Trichoderma lignorum (for example, "Mycotric (registered trademark)" from Futureco Bioscience, ES using strain TL-0601), Trichoderma polysporum 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), Trichoderma viride (e.g., "REMEDIER® WP" from "Isagro Ricerca, ITALIA" using strain ICC080, and "Trianum-P®" from "Koppert" using strain TV1), Tsukamurella paulometabola paurometabola) (for example, "HeberNem®" using strain C-924), Ulocladium oudemansii (for example, "Botry-Zen®" manufactured by "Botry-Zen Ltd, NZ" using strain HRU3, and "BioWorks" using strain U3)"BotryStop" manufactured by "Inc.", Variovorax paradoxus (for example, "Fieldkeeper Wettable Powder (registered trademark)" manufactured by "Central Glass" using strain CGF4526), ​​VA (Vesicular-Arbuscular Mycorrhiza) mycorrhizal fungi (for example, "Dr. Kincon (registered trademark)" manufactured by "Idemitsu Agri"), Verticillium alboatrum (for example, "Dutch Trig (registered trademark)" manufactured by "Tree Care Innovations" using strain WCS850), Verticillium lecanii (for example, "Vertarec (registered trademark)" manufactured by "Arista LifeSciences Inc." using strain IMI 179172, and strain IMI Mycotar (registered trademark) manufactured by Arista LifeScience Co., Ltd. using 263817, Xanthomonas 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 scapterisi Examples include insecticidal / fungicidal strains selected from mutant strains of these strains that possess all the distinguishing characteristics of each strain, or metabolites produced by each strain that exhibit activity against plant pathogenic fungi.

[0077] The following are representative embodiments of the present invention, but the present invention is not limited to these.

[0078] Manufacturing Example 1: Production of B-type crystals of 2-[5-cyclopropyl-3-(ethanesulfonyl)pyridine-2-yl]-5-(trifluoromethanesulfinyl)-1,3-benzoxazole. 4.5 g of compound (1), synthesized according to the method described in Example 1 of Patent Document 4, was added to 5.0 g of chloroform and suspended. After stirring this suspension at room temperature for two weeks, the solid was filtered by suction, and the resulting solid was dried under reduced pressure to obtain 1.7 g of B-type crystals of compound (1). Physical properties: １ H-NMR (CDCl ３ / TMS, ppm) δ 8.77 (d, 1H), 8.32 (s, 1H), 8.13 (d, 1H), 7.91–7.85 (m, 2H), 4.01 (q, 2H), 2.16–2.10 (m, 1H), 1.43 (t, 3H), 1.32–1.27 (m, 2H), 1.00–0.96 (m, 2H) Powder X-ray diffraction measurement: Results are shown in Figure 1. Differential scanning calorimetry: Results are shown in Figure 2. Fourier transform infrared spectroscopy: Results are shown in Figure 3.

[0079] Manufacturing Example 2 Production of B-type crystals of 2-[5-cyclopropyl-3-(ethanesulfonyl)pyridine-2-yl]-5-(trifluoromethanesulfinyl)-1,3-benzoxazole 1.5 g of compound (1), synthesized according to the method described in Patent Document 2, was mixed with 3.0 mL of ethyl acetate and heated to 60°C to dissolve. After cooling the solution to 37°C, a seed crystal of the B-type crystal of compound (1) was added and stirred overnight. 0.7 g of B-type crystals of compound (1) were obtained by filtering the precipitated solid. Powder X-ray diffraction measurement: The results are shown in Figure 4. Differential scanning calorimetry: The results are shown in Figure 5.

[0080] Manufacturing Example 3 Production of B-type crystals of 2-[5-cyclopropyl-3-(ethanesulfonyl)pyridine-2-yl]-5-(trifluoromethanesulfinyl)-1,3-benzoxazole 1.5 g of compound (1), synthesized according to the method described in Patent Document 2, was mixed with 3.0 mL of toluene and heated to 60°C to dissolve. After cooling the solution to 37°C, a seed crystal of the B-type crystal of compound (1) was added and stirred overnight. 1.1 g of B-type crystals of compound (1) was obtained by filtering the precipitated solid. Powder X-ray diffraction measurement: The results are shown in Figure 6. Differential scanning calorimetry: The results are shown in Figure 7.

[0081] Examples of formulations containing the crystals of the present invention are shown below, but the present invention is not limited to these. In the examples of formulations, parts refer to parts by weight.

[0082] Formulation Example 1: Mix and dissolve 10 parts xylene, 70 parts N-methylpyrrolidone, and 10 parts or more of a mixture of polyoxyethylene nonylphenyl ether and alkylbenzene sulfonate calcium to form an emulsion.

[0083] Formulation Example 2. Mix 3 parts of the crystal of the present invention, clay powder, 82 parts of diatomaceous earth powder, and 15 parts or more uniformly and grind to obtain a powder.

[0084] Formulation Example 3. The crystals of the present invention: 5 parts mixed powder of bentonite and clay, 90 parts calcium ligninsulfonate. Mix 5 parts or more of these uniformly, add an appropriate amount of water and knead, then granulate and dry to obtain granules.

[0085] Formulation Example 4. Mix 20 parts of the crystal of the present invention with kaolin, 75 parts of synthetic highly dispersed silicic acid, and 5 parts or more of a mixture of polyoxyethylene nonylphenyl ether and alkylbenzene sulfonate calcium to form a wettable powder by uniformly mixing and grinding them.

[0086] Formulation Example 5. The crystal of the present invention: 10 parts of sodium alkylnaphthalene sulfonate formalin condensate, 1.5 parts of a mixture of dialkyl sulfosuccinate salt, propylene glycol, and water, 1 part of propylene glycol, 10 parts of amorphous silica, 1 part of a mixture of 1,2-benzisothiazolin-3-one, dipropylene glycol, and water, 0.2 parts of water. Mix 76.3 parts or more uniformly and wet grind to obtain a flowable formulation.

[0087] Examples of tests are shown below, but the present invention is not limited to these.

[0088] Test Example 1. Control Value Test against Green Peach Aphid (Myzus persicae) Chinese cabbage was planted in plastic pots 8 cm in diameter and 8 cm in height, and green peach aphids were allowed to breed. The number of parasites in each pot was then investigated. The crystal of the present invention (Type B crystal of compound (1)) was dispersed in water and diluted to a 500 ppm solution. This solution was sprayed onto the stems and leaves of the Chinese cabbage plants in the pots, air-dried, and the pots were stored in a greenhouse. Six days after application, the number of green peach aphids infesting each Chinese cabbage was investigated, and the control value was calculated using the following formula.

[0089]

[0090] Ta: Number of parasites in the treated area before spraying T: Number of parasites in the treated area after spraying Ca: Number of parasites in the untreated area before spraying C: Number of parasites in the untreated area after spraying

[0091] As a result, the crystals of the present invention showed excellent efficacy against the peach aphid.

[0092] Test Example 2. Insecticidal test against Laodelphax striatella. The crystal of the present invention (type B crystal of compound (1)) was dispersed in water and diluted to a 500 ppm solution. Rice seedlings (variety: Nipponbare) were immersed in the solution for 30 seconds, air-dried, and then placed in glass test tubes. Ten third-instar Laodelphax striatella insects were inoculated into each test tube, and cotton plugs were used to check the number of live and dead insects 8 days after inoculation. The corrected mortality rate was calculated using the following formula.

[0093]

[0094] As a result, the crystals of the present invention showed excellent efficacy against the brown planthopper.

[0095] Test Example 3. Insecticide test against diamondback moth (Plutella xylostella) Adult diamondback moths were released into Chinese cabbage seedlings to lay eggs. Two days after release, the seedlings with laid eggs were immersed for approximately 30 seconds in a solution of the present invention (type B crystal of compound (1)) diluted with water to 500 ppm. After air drying, the seedlings were left to stand in a constant temperature room at 25°C. Six days after immersion in the solution, the number of hatched insects was investigated, and the corrected mortality rate was calculated using the following formula.

[0096]

[0097] As a result, the crystals of the present invention showed excellent efficacy against diamondback moths.

[0098] Test Example 4. Insecticidal Test 2 against Diamondback Moth (Plutella xylostella) A solution containing the crystal of the present invention (Type B crystal of compound (1)) as the active ingredient was diluted to 0.1 ppm with water. Cabbage leaf pieces were immersed in this solution for approximately 30 seconds, air-dried, and then placed in a plastic petri dish. Five third-instar diamondback moth larvae were inoculated into the petri dish, and the dish was covered and left undisturbed in a constant temperature room at 25°C. Four days after inoculation, the number of surviving insects was investigated, and the corrected mortality rate was calculated using the following formula. The determination was made according to the following criteria. In determining viability, individuals that could not walk normally were treated as dead.

[0099] Criteria for evaluation: A... Corrected mortality rate of 99% or higher B... Corrected mortality rate of 80-98% C... Corrected mortality rate of 70-79% D... Corrected mortality rate of 50-69% E... Corrected mortality rate of less than 50%

[0100] The results of this test showed that the crystals of the present invention were effective against diamondback moths, receiving an A rating.

[0101] Test Example 5. Insecticidal test against Spodoptera litura. Cabbage leaf fragments were immersed for approximately 30 seconds in a solution prepared by diluting the active ingredient of the present invention's crystal (Type B crystal of compound (1)) with water to 1 ppm. After air drying, the fragments were placed in a plastic petri dish, and five third-instar larvae of Spodoptera litura were inoculated. The dish was then covered and left undisturbed in a constant temperature room at 25°C. Four days after inoculation, the number of surviving insects was investigated, and the corrected mortality rate was calculated using the following formula. The determination was made according to the following criteria. In determining viability, individuals unable to walk normally were treated as dead.

[0102] Criteria for evaluation: A... Corrected mortality rate of 99% or higher B... Corrected mortality rate of 80-98% C... Corrected mortality rate of 70-79% D... Corrected mortality rate of 50-69% E... Corrected mortality rate of less than 50%

[0103] The results of this test showed that the crystals of the present invention were effective against the beet armyworm, receiving an A rating.

[0104] Test Example 6. Insecticidal test against Helicoverpa armigera. Cabbage leaf fragments were immersed for approximately 30 seconds in a solution prepared by diluting the active ingredient of the crystal of the present invention (type B crystal of compound (1)) with water to 0.1 ppm. After air drying, the fragments were placed in a plastic petri dish, and three fourth-instar larvae of Helicoverpa armigera were inoculated. The dish was then covered and left undisturbed in a constant temperature room at 25°C. Four days after inoculation, the number of surviving insects was investigated, and the corrected mortality rate was calculated using the following formula. The determination was made according to the following criteria. In determining viability, individuals that could not walk normally were treated as dead.

[0105] Criteria for evaluation: A... Corrected mortality rate of 99% or higher B... Corrected mortality rate of 80-98% C... Corrected mortality rate of 70-79% D... Corrected mortality rate of 50-69% E... Corrected mortality rate of less than 50%

[0106] The results of this test showed that the crystals of the present invention demonstrated an A-grade effectiveness against the tobacco budworm.

[0107] Test Example 7. Insecticidal test against Homona magnanima Two hardened tea leaves were immersed for approximately 30 seconds in a solution of the active ingredient crystal of the present invention (Type B crystal of compound (1)) diluted with water to 10 ppm, and after air drying, placed in a plastic petri dish. Five fourth-instar larvae of the tea leaf roller were inoculated, and the dish was covered and left undisturbed in a constant temperature room at 25°C. Four days after inoculation, the number of surviving insects was investigated, and the corrected mortality rate was calculated using the following formula. The determination was made according to the following criteria. In determining viability, individuals that could not walk normally were treated as dead.

[0108] Criteria for evaluation: A... Corrected mortality rate of 99% or higher B... Corrected mortality rate of 80-98% C... Corrected mortality rate of 70-79% D... Corrected mortality rate of 50-69% E... Corrected mortality rate of less than 50%

[0109] The results of this test showed that the crystal of the present invention demonstrated an A-grade effect against tea tortrix.

[0110] Test Example 8. Insecticidal test against cucumber beetle (Aulacophora femoralis) Cucumber leaf fragments were immersed for approximately 30 seconds in a solution of the active ingredient crystal of the present invention (Type B crystal of compound (1)) diluted with water to 1 ppm, and after air drying, placed in a plastic petri dish. Three adult cucumber beetles were inoculated, the dish was covered, and left undisturbed in a constant temperature room at 25°C. Four days after inoculation, the number of surviving insects was investigated, and the corrected mortality rate was calculated using the following formula. The determination was made according to the following criteria. In determining viability, individuals that could not walk normally were treated as dead.

[0111] Criteria for evaluation: A... Corrected mortality rate of 99% or higher B... Corrected mortality rate of 80-98% C... Corrected mortality rate of 70-79% D... Corrected mortality rate of 50-69% E... Corrected mortality rate of less than 50%

[0112] The results of this test showed that the crystals of the present invention were effective against cucumber beetles, receiving an A rating.

[0113] Test Example 9. Insecticidal test against cotton aphid (Aphis gossypii) Cucumber leaf pieces were immersed for approximately 30 seconds in a 1 ppm solution of the active ingredient crystal of the present invention (type B crystal of compound (1)), air-dried, placed in a plastic petri dish, inoculated with 8 adult cotton aphids, and left to stand in a constant temperature room at 25°C. Four days after inoculation, the number of surviving insects was investigated, the control efficacy was calculated using the following formula, and the evaluation was made according to the following criteria. The same test was performed on type A crystal of compound (1), and the control efficacy was calculated and evaluated.

[0114] Ta: Number of parasites in the treated area before spraying T: Number of parasites in the treated area after spraying Ca: Number of parasites in the untreated area before spraying C: Number of parasites in the untreated area after spraying

[0115] Evaluation Criteria A: Control value of 99 or higher B: Control value of 80-98 C: Control value of 70-79 D: Control value of 50-69 E: Control value of less than 50

[0116] The results of this test showed that the crystals of the present invention exhibited an A rating for control against cotton aphids. On the other hand, the A-type crystals of compound (1) exhibited a C rating for control against cotton aphids.

[0117] Test Example 10. Insecticidal test against the peach aphid (Myzus persicae) (systemic action test) 5 mL of a solution containing the crystal of the present invention (type B crystal of compound (1)) as the active ingredient was diluted to 1 ppm with water and placed in a plastic cup. The roots of Chinese cabbage seedlings were then immersed in the solution. Subsequently, 20 peach aphids were inoculated into the stems and leaves, and the plants were left to stand in a constant temperature room at 25°C. Five days after inoculation, the number of surviving insects was investigated, and the control efficacy was calculated using the following formula and judged according to the following criteria.

[0118] Ta: Number of parasites in the treated area before spraying T: Number of parasites in the treated area after spraying Ca: Number of parasites in the untreated area before spraying C: Number of parasites in the untreated area after spraying

[0119] Evaluation Criteria A: Control value of 99 or higher B: Control value of 80-98 C: Control value of 70-79 D: Control value of 50-69 E: Control value of less than 50

[0120] The results of this test showed that the crystals of the present invention exhibited a pest control efficacy rating of A.

[0121] Test Example 11. Insecticidal test against Spodoptera litura (systemic action test) 5 mL of a solution containing the crystal of the present invention (type B crystal of compound (1)) as the active ingredient, diluted to 0.1 ppm with water, was placed in a plastic cup, and the roots of Chinese cabbage seedlings were immersed in it. Then, five first-instar larvae of Spodoptera litura were inoculated into the stems and leaves, and the plants were left standing in a constant temperature room at 25°C. Five days after inoculation, the number of surviving insects was investigated, and the corrected mortality rate was calculated using the following formula, with evaluation performed according to the following criteria. In addition, an observation survey was conducted to evaluate the area of ​​feeding damage. In determining survival, individuals that could not walk normally were treated as dead. The same test was performed for type A crystal of compound (1), and the corrected mortality rate and feeding damage area were calculated and evaluated.

[0122] Criteria for evaluation: A... Corrected mortality rate of 99% or higher B... Corrected mortality rate of 80-98% C... Corrected mortality rate of 70-79% D... Corrected mortality rate of 50-69% E... Corrected mortality rate of less than 50%

[0123] The results of this test showed that the crystals of the present invention were rated A, and the area damaged by insects decreased by 88% compared to the untreated area. On the other hand, the A-type crystals of compound (1) were rated C, and no reduction in the area damaged by insects was observed compared to the untreated area.

[0124] The crystals of the present invention have excellent efficacy as a pest control agent (for example, a pest control agent for agricultural and horticultural use).

Claims

1. Compound represented by formula (1): A crystal of the compound represented by the formula, having diffraction peaks at diffraction angles (2θ) of 9.4 ± 0.2°, 13.4 ± 0.2°, 16.1 ± 0.2°, 18.6 ± 0.2° and 22.5 ± 0.2° in the powder X-ray diffraction spectrum.

2. The crystal according to claim 1, which is shown to have a melting point of 123 to 135°C by differential scanning calorimetry (DSC).

3. In the infrared absorption spectrum, the wavenumber is 1312 ± 4 cm⁻¹. －１ , 1174±4cm －１ , 1135±4cm －１ , 1073±4cm －１ , 845±4cm －１ , 818±4cm －１ 725±4cm －１ and 670±4cm －１ The crystal according to claim 1, having a peak at the position.

4. Formula (1): A method for producing crystals of a compound represented by formula (1), comprising the steps of suspending the compound represented by formula (1) in a solvent containing at least one halogenated hydrocarbon, and stirring the resulting slurry, as described in any one of claims 1 to 3.

5. Formula (1): A method for producing crystals of a compound represented by formula (1), comprising the steps of dissolving the compound represented by formula (1) in a solvent containing at least one selected from the group consisting of aromatic hydrocarbons and esters, and precipitating crystals from the resulting solution, wherein seed crystals may be added in the step of precipitating the crystals, as described in any one of claims 1 to 3.

6. A pest control agent characterized by containing the crystal described in any one of claims 1 to 3 as an active ingredient.

7. A method for using an insecticide, characterized by applying an effective amount of the insecticide described in claim 6 to a target plant or soil.

8. A method for controlling pests, characterized by applying an effective amount of the pest control agent described in claim 6 to a target plant or soil.

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