Acrylic acid derivative and use thereof

Abstract

The present invention provides a compound having excellent plant disease control efficacy. The compound represented by formula (A) can be used for plant disease control.

Description

Acrylic acid derivatives and their uses

[0001] This application claims priority to and the benefit of Japanese Patent Application No. 2023-117361, filed on July 19, 2023, the entire contents of which are incorporated herein by reference. The present invention relates to an acrylic acid derivative and uses thereof.

[0002] Non-Patent Document 1 describes compounds that exhibit plant disease control effects.

[0003] The Pesticide Manual-18th Edition (BCPC); ISBN 978-1-9998966-1-4

[0004] An object of the present invention is to provide a compound having excellent plant disease control activity.

[0005] As a result of investigations into the above-mentioned problems, the present inventors have found that a compound represented by the following formula (A) has excellent plant disease control activity, and have arrived at the present invention. That is, the present invention is as follows: [1] Formula (A) (hereinafter referred to as the compound of the present invention). [2] A composition for controlling plant diseases, which contains the compound according to [1] and an inert carrier (hereinafter referred to as the plant disease control composition of the present invention). [3] A composition containing one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and the compound according to [1]: Group (a): a group consisting of an insecticidal active component, an acaricidal active component, and a nematicidal active component; Group (b): a fungicidal active component; Group (c): a plant growth regulator component; Group (d): a repellent component. [4] A method for controlling plant diseases, which comprises applying an effective amount of the compound according to [1], an effective amount of the plant disease control composition according to [2], or an effective amount of the composition according to [3] to a plant or soil in which the plant is grown (hereinafter referred to as the plant disease control method of the present invention). [5] Use of the compound according to [1], the plant disease control composition according to [2], or the composition according to [3] for controlling plant diseases. [6] A seed or a vegetative reproductive organ carrying an effective amount of the compound according to [1], an effective amount of the plant disease control composition according to [2], or an effective amount of the composition according to [3].

[0006] The compound of the present invention has excellent plant disease control activity and is effective as an active ingredient of a composition for controlling plant diseases.

[0007] The compound of the present invention exists in two stereoisomers. Types of stereoisomers include diastereomers. The compound of the present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.

[0008] As a stereoisomer, the formula (1) and a compound represented by formula (2) The compound represented by formula (1) and the compound represented by formula (2) are diastereomers of each other.

[0009] The following compounds are examples of the compound of the present invention: A compound represented by formula (1). A compound represented by formula (2). A stereoisomeric mixture containing more of the compound represented by formula (1) than the compound represented by formula (2). A stereoisomeric mixture containing more of the compound represented by formula (2) than the compound represented by formula (1). A stereoisomeric mixture containing the compound represented by formula (1) and the compound represented by formula (2) in a 1:1 ratio.

[0010] The compound of the present invention can be mixed or used in combination with one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) below (hereinafter referred to as the present component). The term "mixed or used in combination" means that the compound of the present invention and the present component are used simultaneously, separately, or with a time interval. When the compound of the present invention and the present component are used simultaneously, the compound of the present invention and the present component may be contained in separate preparations or in a single preparation. One aspect of the present invention is a composition (hereinafter referred to as Composition A) containing one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) (i.e., the present component) and the compound of the present invention.

[0011] Group (a) includes acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABAergic chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, multisite inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial insect midgut membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complexes I and II, The group consisting of inhibitors of classes III and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal organ modulators, microbial insecticides, and other insecticidal, acaricidal, and nematicidal active ingredients, which are described in the IRAC mechanism-based classification.

[0012] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acylamino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multisite contact-active fungicides, microbial fungicides, and other fungicidal active ingredients. These are listed in the FRAC classification based on the mechanism of action.

[0013] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).

[0014] Group (d) is a group of repellent ingredients.

[0015] Examples of combinations of the present component and the compound of the present invention are described below. For example, alanycarb + SX refers to a combination of alanycarb and SX. The abbreviation SX refers to the compound of the present invention. All of the present components described below are known components and can be obtained from commercially available preparations or produced by known methods. When the present component is a microorganism, it can also be obtained from a bacterial depository. The number in parentheses indicates the CAS RN (registered trademark).

[0016] Combinations of the present ingredient of the above group (a) with the compound of the present invention: abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acinonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide + SX, Amitraz + SX, azadirachtin + SX, azamethiphos + SX, azinphos-ethyl + SX, azinphos-methyl + SX, azocyclotin + SX, Celastrus angulatus bark + SX, bendiocarb + SX, benfluthrin + SX, benfuracarb + SX, bensultap + SX, benzoximate + SX, benzpyrimoxan + SX, beta-cyfluthrin + SX, beta-cypermethrin + SX, bifenazate + SX, bifenthrin + SX, bioallethrin + SX,Bioresmethrin + SX, bistrifluron + SX, borax + SX, boric acid + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphide + SX, carbaryl + SX, carbofuran + SX, carbosulfan + SX, cartap hydrochloride + SX, cartap + SX Chinomethionate + SX, chlorantraniliprole + SX, chlordane + SX, chlorethoxyfos + SX, chlorfenapyr + SX, chlorfenvinphos + SX, chlorfluazuron + SX, chlormephos + SX, chloropicrin + SX, chlorpyrifos + SX, chlorpyrifos-methyl + SX, chromafenozide + SX, clofentezine + SX, clothianidin + SX, concanamycin A A) + SX, coumaphos + SX, cryolite + SX, cyanophos + SX, cyantraniliprole + SX,Cyclaniliprole + SX, cyclobutrifluram + SX, cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyetpyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, cyphenothrin + SX, cyproflanilide + SX, cyromazine + SX, Dazomet + SX, deltamethrin + SX, demeton-S-methyl + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, dichloromezotiaz + SX, dicofol + SX, dicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, Dinotefuran + SX, disodium octaborate + SX, disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, doramectin + SX,Dried leaves of Dryopteris filix (mas) + SX, emamectin benzoate + SX, empenthrin + SX, endosulfan + SX, EPN (O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, epsilon-metofluthrin + SX, epsilon-momfluorothrin + SX, esfenvalerate + SX, ethifencarb + SX, ethion + SX, ethiprole + SX, ethoprophos + SX, etofenprox + SX. Etoxazole + SX, Artemisia absinthium extract + SX, Azadirachta indica extract + SX, Cassia nigricans extract + SX, Clitoria ternatea extract + SX, Symphytum officinale extract + SX, Chenopodium ambrosioides extract + SX, Tansy extract + SX, Urtica dioica extract + SX, Viscum album extract + SX, Famphur + SX, Fenamiphos + SX Fenazaquin + SX,Fenbutatin oxide + SX, fenitrothion + SX, fenmezoditiaz + SX, fenobucarb + SX, fenoxycarb + SX, fenpropathrin + SX, fenpyroximate + SX, fenthion + SX, fenvalerate + SX, fipronil + SX, flometoquin + SX, flonicamid + SX, fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, Flubendiamide + SX, fluchlordiniliprole + SX, flucycloxuron + SX, flucythrinate + SX, fluensulfone + SX, flufenprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, flupyroxystrobin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX, formetanate + SX, fosthiazate + SX, furamethrin + SX,Furathiocarb + SX, gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, potassium salt of hop beta acid + SX, hydramethylnon + SX, hydroprene + SX, imicyafos + SX, Imidacloprid + SX, imidaclothiz + SX, imiprothrin + SX, indazapyroxamet + SX, indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoprocarb + SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappa-tefluthrin + SX Kappa-bifenthrin + SX, kinoprene + SX, lambda-cyhalothrin + SX, ledprona + SX, lenoremycin + SX,Lepimectin + SX, lime sulfur + SX, lotilaner + SX, lufenuron + SX, machine oil + SX, malathion + SX, mecarbam + SX, meperfluthrin + SX, metaflumizone + SX, metam + SX, methamidophos + SX, methidathion + SX, methiocarb + SX, methomyl + SX, methoprene + SX, methoxychlor + SX, methoxyfenozide + SX, Methyl bromide + SX, metofluthrin + SX, metolcarb + SX, metoxadiazone + SX, mevinphos + SX, milbemectin + SX, milbemycin oxime + SX, mivorilaner + SX, modoflaner + SX, momfluorothrin + SX, monocrotophos + SX, moxidectin + SX, naled + SX, nicofluprole + SX, nicotine + SX, nicotine sulfate + SX, Nitenpyram + SX, Novaluron + SX, Noviflumuron + SX,Chenopodium anthelminticum seed oil + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX, permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX, phosalone + SX, phosmet + SX, phosphamidon + SX, phosphine + SX, phoxim + SX Pirimicarb + SX, pirimiphos-methyl + SX, prallethrin + SX, profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX, propylene glycol alginate + SX, prothiofos + SX, pyflubumide + SX, pymetrozine + SX, pyraclofos + SX, pyrethrins + SX, pyridaben + SX, pyridalyl + SX, Pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX,Pyriminostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate + SX, sodium metaborate + SX, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidione + SX, spirotetramat + SX, sulfiflumin + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride + SX, tartar emetic + SX, tau-fluvalinate + SX, tebufenozide + SX, Tebufenpyrad + SX, Tebupirimfos + SX, Teflubenzuron + SX, Tefluthrin + SX, Temephos + SX, Terbufos + SX,Terpene constituents of the extract of Chenopodium ambrosioides near ambrosioides + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, tetraniliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, Thiometon + SX, thiosultap disodium + SX, thiosultap monosodium + SX, tigolaner + SX, thioantraniliprole + SX, tioxazafen + SX, tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX, triazamate + SX, triazophos + SX, trichlorfon + SX, trifluenfuronate + SX, triflumezopyrim + SX, Triflumuron + SX, trimethacarb + SX,Tyclopyrazoflor + SX, umifoxolaner + SX, vamidothion + SX, Quassia amara wood extract + SX, 3,5-dimethylphenyl N-methylcarbamate (XMC) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methanesulfonyl)propanamide + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX,2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX, BT crop protein Cry1Ab (BT crop protein Cry1Ab) + SX, BT crop protein Cry1Ac (BT crop protein Cry1Ac) + SX, BT crop protein Cry1Fa (BT crop protein Cry1Fa) + SX, BT crop protein Cry1A.105 (BT crop protein Cry1A.105) + SX, BT crop protein Cry2Ab (BT crop protein Cry2Ab) + SX,BT crop protein Vip3A + SX, BT crop protein mCry3A + SX, BT crop protein Cry3Ab + SX, BT crop protein Cry3Bb + SX, BT crop protein Cry34Ab1 / Cry35Ab1 + SX, Adoxophyes orana granulovirus BV-0001 + SX, Anticarsia gemmatalis MNPV (multiple nucleocapsid nucleopolyhedrovirus) + SX, Autographa californica MNPV + SX, Cydia pomonella GV strain V15 + SX, Cydia pomonella GV strain V22 + SX, Cryptophlebia leucotreta GV + SX, Dendrolimus punctatus cypovirus + SX, Helicoverpa armigera nucleopolyhedrovirus BV-0003 + SX, Helicoverpa zea ... NPV) + SX, Lymantria dispar NPV + SX, Mamestra brassicae NPV + SX,Mamestra configurata nucleopolyhedrosis virus (NPV) + SX, Neodiprion abietis nucleopolyhedrosis virus (NPV) + SX, Neodiprion lecontei nucleopolyhedrosis virus (NPV) + SX, Neodiprion sertifer nucleopolyhedrosis virus (NPV) + SX, Nosema locustae + SX, Orgyia pseudotsugata nucleopolyhedrosis virus (NPV) + SX, Pieris rapae granulosis virus (GV) + SX, Plodia interpunctella granulosis virus (GV) + SX, Spodoptera exigua MNPV + SX, Spodoptera littoralis MNPV + SX, Spodoptera littoralis NPV + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b+ SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus thuringiensis strain AQ52 + SX,Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX, Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX,Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. dendrolimus + SX, Bacillus thuringiensis var. galleriae + SX, Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var. japonensis strain buibui + SX, Bacillus thuringiensis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var. T36 + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX, Beauveria bassiana strain GHA + SX, Beauveria brongniartii + SX, Burkholderia rinogensis strain A396 + SX,Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dectylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii strain KV01 + SX, Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX, Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX,Wolbachia pipientis + SX。,

[0017] Combinations of the present ingredient of the above group (b) with the compound of the present invention: acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, Benthiavalicarb-isopropyl + SX, benzovindiflupyr + SX, binapacryl + SX, biphenyl + SX, bitertanol + SX, bixafen + SX, blasticidin S + SX, Bordeaux mixture + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionate + SX, chitin + SX, chloroinconazide + SX, chloroneb + ​​SX,Chlorothalonil + SX, chlozolinate + SX, colletochlorin B + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, copper oxychloride + SX, copper(II) sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + SX, cyproconazole + SX, cyprodinil + SX, dichlobentiazox + SX, Dichlofluanid + SX, diclocymet + SX, diclomezine + SX, dicloran + SX, diethofencarb + SX, difenoconazole + SX, diflumetorim + SX, dimethachlone + SX, dimethirimol + SX, dimethomorph + SX, dimoxystrobin + SX, diniconazole + SX, diniconazole-M + SX, dinocap + SX, dipotassium hydrogenphosphite + SX, dipymetitrone + SX, dithianon + SX,Dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt + SX, dodemorph + SX, dodine + SX, edifenphos + SX, enoxastrobin + SX, epoxiconazole + SX, etaconazole + SX, ethaboxam + SX, ethirimol + SX, etridiazole + SX, garlic extract (Allium sativum) + SX, extract of the cotyledons of lupine plantlets (BLAD) + SX, horsetail extract (Equisetum arvense) + SX SX, tea tree extract (Melaleuca alternifolia) + SX, giant knotweed extract (Reynoutria sachalinensis) + SX, nasturtium extract (Tropaeolus majus) + SX, famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fenarimol + SX, fenbuconazole + SX, fenfuram + SX, fenhexamid + SX, fenoxanil + SX, fenpiclonil + SX, fenpicoxamid + SX Fenpropidin + SX, Fenpropimorph + SX,Fenpyrazamine + SX, triphenyltin acetate + SX, triphenyltin chloride + SX, fentin hydroxide + SX, ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, flufenoxadiazam + SX, flufenoxystrobin + SX, fluindapyr + SX, flumetylsulforim + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, folpet + SX, Fosetyl + SX, fosetyl-aluminium + SX, fuberidazole + SX, furalaxyl + SX, furametpyr + SX,Guazatine + SX, hexaconazole + SX, hymexazole + SX, imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX, ipfentrifluconazole + SX, ipflufenoquin + SX, iprobenfos + SX, iprodione + SX, iprovalicarb + SX Isofetamide + SX, isoflucipram + SX, isoprothiolane + SX, isopyrazam + SX, isotianil + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX, oak leaves and bark of quercus + SX, mancozeb + SX, mandestrobin + SX, mandipropamid + SX, maneb + ​​SX, mefentrifluconazole + SX, mepanipyrim + SX, Mepronil + SX, meptyldinocap + SX, metalaxyl + SX, metalaxyl-M + SX, metarylpicoxamid + SX,Metconazole + SX, methasulfocarb + SX, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, octhilinone + SX, ofurace + SX, orysastrobin + SX, oxadixyl + SX, oxathiapiprolin + SX, oxine-copper + SX, oxolinic acid + SX, Oxpoconazole + SX, oxpoconazole fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, penthiopyrad + SX, phenamacril + SX, phosphorous acid + SX, phthalide + SX, picarbutrazox + SX, picoxystrobin + SX, piperalin + SX, polyoxins + SX, Potassium hydrogencarbonate + SX, potassium dihydrogenphosphite + SX,Methyl 3-methoxy-2-((4-methyl-[1,1'-biphenyl]-3-yl)oxy)acrylate + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + ​​SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, pyraclostrobin + SX, pyrametostrobin + SX, pyraoxystrobin + SX SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridaclomethyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriophenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SX, quinconazole + SX, quinofumelin + SX, Quinoxyfen + SX, Quintozene + SX, Saponins of Chenopodium quinoa + SX, Seboctylamine + SX,Sedaxane + SX, silthiofam + SX, simeconazole + SX, sodium hydrogencarbonate + SX, spiroxamine + SX, streptomycin + SX, sulfur + SX, tebuconazole + SX, tebufloquin + SX, teclofthalam + SX, tecnazene + SX, terbinafine + SX, tetraconazole + SX, thiabendazole + SX, thifluzamide + SX, thiophanate + SX, Thiophanate-methyl + SX, thiram + SX, thymol + SX, tiadinil + SX, tolclofos-methyl + SX, tolfenpyrad + SX, tolprocarb + SX, tolylfluanid + SX, triadimefon + SX, triadimenol + SX, triazoxide + SX, triclopyricarb + SX, tricyclazole + SX, tridemorph + SX, trifloxystrobin + SX, triflumizole + SX, Triforine + SX, triticonazole + SX, validamycin + SX, valifenalate + SX,ビンクロゾリン(vinclozolin) + SX, マスタードパウダー(yellow mustard powder) + SX, zinc thiazole + SX, ジネブ(zineb) + SX, ジラム(ziram) + SX, ゾキサミド(zoxamide) + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX,N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S,5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX,2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX,N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX,N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxetan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxolan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxan-4-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX,5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX,(5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, methyl ({5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate + SX, methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate + SX,methyl (Z)-2-[(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenoxy]-3-methoxyprop-2-enoate + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinolin-4(3H)-one + SX, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo(Trademark) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX,Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002 + SX,Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX,Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SX, Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX,Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX,Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX。,

[0018] Combinations of the present ingredient in group (c) above with the compound of the present invention: 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, (1H-indol-3-yl)acetic acid (IAA) + SX, 4-(1H-indol-3-yl)butyric acid (IBA) + SX, 2-(4-chloro-2-methylphenoxy)acetic acid (MCPA) + SX, 4-(4-chloro-2-methylphenoxy)butyric acid (MCPB) + SX, 4-chlorophenoxyacetic acid (4-CPA) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat chloride + SX, chlorpropham + SX, choline chloride + SX, cloprop + SX, cyanamide + SX, Cyclanilide + SX,Daminozide + SX, decan-1-ol + SX, dichlorprop + SX, dikegulac + SX, dimethipin + SX, diquat + SX, ethephon + SX, ethychlozate + SX, flumetralin + SX, flurprimidol + SX, forchlorfenuron + SX, formononetin + SX, gibberellin A + SX, gibberellin A3 + SX, inabenfide + SX, Kinetin + SX, lipochitooligosaccharide SP104 + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexadione calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, sintophen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate + SX, Thidiazuron + SX, triapenthenol + SX, tribufos + SX, trinexapac-ethyl + SX,Uniconazole-P + SX, 2-(naphthalen-1-yl)acetamide + SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid + SX, Methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol + SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 197198 + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense XOH + SX, Azospirillum brasilense Ab-V5 + SX, Azospirillum brasilense Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium elkanii SEMIA 5019 + SX, Bradyrhizobium japonicum TA-11 + SX,Bradyrhizobium japonicum USDA 110 + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Mesorhizobium loti + SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. Viciae + SX, Rhizobium trifolii + SX, Rhizobium tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, Zucchini Yellow Mosaik Virus weak strain + SX. ,

[0019] Combinations of the present component of the above group (d) with the compound of the present invention: anthraquinone + SX, deet + SX, icaridin + SX.

[0020] The ratio of the compound of the present invention to the present component is not particularly limited, and examples thereof include a weight ratio (compound of the present invention:present component) of 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, and the like.

[0021] The compound of the present invention can control plant diseases caused by plant pathogenic microorganisms such as fungi, oomycetes, Phytomyxea, and bacteria. Examples of fungi include Ascomycota, Basidiomycota, Blastocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specific examples include the following: The scientific name of the plant pathogenic microorganism that causes each disease is shown in parentheses.

[0022] Diseases of rice: blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), yellowing and withering disease (Sclerophthora macrospora), false blast and panicle blight (Epicoccum nigrum), seedling blight (Trichoderma viride, Rhizopus oryzae), sheath blight-like symptoms (red sclerotium pathogen (Waitea circinata), brown sclerotium pathogen (Ceratobasidium setariae), brown sheath blight pathogen (Thanatephorus cucumeris)), false smut (Ustilaginoidea virens), black kernel smut (Tilletia horrida, Tilletia barclayana);Wheat diseases: Powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia recondita), pink snow blight (Microdochium nivale, Microdochium majus), small snow blight (Typhula incarnata, Typhula ishikariensis), large snow blight (Sclerotinia borealis), brown snow blight (Pythium spp.), naked smut (Ustilago tritici), grass smut (Tilletia caries, Tilletia controversa), eyespot (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), rotten blight (Stagonospora nodorum), yellow spot (Pyrenophora tritici-repentis), seedling damping off caused by Rhizoctonia fungi (Rhizoctonia solani), damping off (Gaeumannomyces graminis), rice blast (Pyricularia graminis-tritici);Barley diseases: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), small rust (Puccinia hordei), ear bunt (Ustilago nuda), scald (Rhynchosporium secalis), net blotch (Pyrenophora teres), leaf spot (Cochliobolus sativus), leaf spot (Pyrenophora graminea), leaf spot (Ramularia collo-cygni), seedling damping-off (Rhizoctonia solani); corn diseases: rust (Puccinia sorghi), southern rust (Puccinia polysora), sooty blight (Setosphaeria turcica), tropical rust (Physopella zeae), southern leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (Cercospora zeae-maydis), brown spot (Kabatiella zeae), Phaeosphaeria leaf spot (Phaeosphaeria maydis), Diplodia disease (Stenocarpella maydis, Stenocarpella macrospora), stalk rot (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis), Physoderma maydis, tar spot (Phyllachora maydis);Cotton diseases: anthracnose (Colletotrichum gossypii), white mold (Ramularia areola), black spot (Alternaria macrospora, Alternaria gossypii), black root rot (Thielaviopsis basicola); coffee diseases: rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola); rapeseed diseases: sclerotinia sclerotiorum, black spot (Alternaria brassicae), root rot (Phoma lingam), light leaf spot (Pyrenopeziza brassicae); sugarcane diseases: rust (Puccinia melanocephela, Puccinia kuehnii), smut (Ustilago scitaminea); sunflower diseases: rust (Puccinia helianthi), downy mildew (Plasmopara Citrus diseases: black spot (Diaporthe citri), scab (Elsinoe fawcetti), green mold (Penicillium digitatum), blue mold (Penicillium italicum), late blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillus niger;Apple diseases: Monilinia mali, canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), leaf spot (Alternaria alternata apple pathotype), black spot (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring spot (Botryosphaeria berengeriana), late blight (Phytophtora cactorum), red spot (Gymnosporangium juniperi-virginianae, Gymnosporangium yamadae); Pear diseases: black spot (Venturia nashicola, Venturia pirina), black spot (Alternaria alternata Japanese pear pathotype), red spot (Gymnosporangium haraeanum); Peach diseases: brown rot (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis rot (Phomopsis sp.), leaf crinkle (Taphrina deformans), powdery mildew (Podosphaera leucotricha); grape diseases: black rot (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Neophysopella sp.), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola), brown spot (Pseudocercospora vitis), white rot (Coniella castaneicola); persimmon diseases: anthracnose (Gloeosporium kaki, Colletotrichum acutatum), leaf drop (Cercospora kaki, Mycosphaerella nawae), powdery mildew (Phyllactinia kakicola);Fig diseases: Rust (Phakopsora nishidana); Cucurbit diseases: Anthracnose (Colletotrichum lagenarium), Powdery mildew (Sphaerotheca fuliginea), Blight (Didymella bryoniae), Brown spot (Corynespora cassiicola), Blight (Fusarium oxysporum), Downy mildew (Pseudoperonospora cubensis), Late blight (Phytophthora capsici), Damping-off (Pythium sp.), Root rot (Phomopsis sp.); Tomato diseases: Ring spot (Alternaria solani), Leaf mold (Cladosporium fulvum), Leaf mold (Pseudocercospora fuligena), Late blight (Phytophthora infestans), Powdery mildew (Leveillula taurica); Diseases of eggplant: brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum), black blight (Corynespora melongenae), sooty mold (Mycovellosiella nattrassii), brown spot (Thanatephorus cucumeris); diseases of cruciferous vegetables: black spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), white rust (Albugo candida), sooty mold (Alternaria brassicicola); diseases of leeks: rust (Puccinia allii), black spot (Alternaria porri), black rot (Sclerotium cepivorum), small sclerotial rot (Botrytis squamosa), leaf blight (Stemphylium vesicarium, Stemphylium botryosum), white silk disease (Sclerotium rolfsii), white spot leaf blight (Botrytis squamosa);Soybean diseases: Purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), brown ring spot (Corynespora cassiicola), anthracnose (Colletotrichum glycines, Colletotrichum truncatum), leaf rot (Rhizoctonia solani), brown spot (Septoria glycines), leaf spot (Cercospora sojina), sclerotinia sclerotiorum, powdery mildew (Microsphaera diffusa), stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme), black root rot (Calonectria ilicicola), Diaporthe / Phomopsis Diseases of common beans: Sclerotinia sclerotiorum, rust (Uromyces appendiculatus), angular spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), root rot (Fusarium solani); Diseases of peanuts: black spot (Cercospora personata), brown spot (Cercospora arachidicola), southern blight (Sclerotium rolfsii), black root rot (Calonectria ilicicola); Diseases of peas: powdery mildew (Erysiphe pisi), root rot (Fusarium solani);Potato diseases: summer blight (Alternaria solani), late blight (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery scab (Spongospora subterranea f. sp. subterranea), verticillium wilt (Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens), dry rot (Fusarium solani), canker (Synchytrium endobioticum); strawberry diseases: powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella cingulata, Colletotrichum acutatum); tea diseases: net blight (Exobasidium reticulatum), white spot (Elsinoe leucospila), ring spot (Pestalotiopsis Diseases of tobacco: red spot (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae); Diseases of sugar beet: brown spot (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root rot (Aphanomyces cochlioides), rust (Uromyces betae); Diseases of rose: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); Diseases of chrysanthemum: brown spot (Septoria chrysanthemi indici), white rust (Puccinia horiana); Onion diseases: white spotted leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), small sclerotial rot (Botrytis squamosa);Diseases of various crops: gray mold (Botrytis cinerea), sclerotinia sclerotiorum, black rot (Sclerotium cepivorum), southern blight (Sclerotium rolfsii), damping-off (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum); diseases of radish: black spot (Alternaria brassicicola); diseases of sweet potato: fusarium wilt (Fusarium oxysporum f. sp. batatas), root rot (Diaporthe destruens), black spot (Ceratocystis fimbriata); diseases of turfgrass: dollar spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), red blight (Pythium aphanidermatum), anthracnose (Colletotrichum caudatum); banana disease: Sigatoka (Mycosphaerella fijiensis, Mycosphaerella musicola); lentil disease: Ascochyta (Ascochyta lentis); chickpea disease: Ascochyta (Ascochyta rabiei); bell pepper disease: anthracnose (Colletotrichum scovillei), powdery mildew (Leveillula taurica), southern blight (Sclerotium rolfsii); mango disease: anthracnose (Colletotrichum acutatum); sweet potato disease: root rot (Diaporthe destruens); fruit tree diseases: white root rot (Rosellinia necatrix), purple root rot (Helicobasidium mompa); post-harvest fruit diseases of apples, pears, etc.: mucor rot (Mucor piriformis);Seed diseases or diseases in the early stages of growth caused by species of the genera Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, Diplodia, etc.; viral diseases: big vein disease of lettuce transmitted by Olpidium brassicae, viral diseases of various crops transmitted by the genus Polymyxa (e.g., Polymyxa betae and Polymyxa graminis); diseases caused by bacteria: bacterial seedling blight of rice (Burkholderia plantarii), inner gluten browning of rice (Pantoea ananatis), bacterial leaf blight of rice (Xanthomonas oryzae pv. oryzae.), bacterial spot of cucumber (Pseudomonas syringae pv. lachrymans), eggplant bacterial wilt (Ralstonia solanacearum), citrus canker (Xanthomonas citri), Chinese cabbage soft rot (Erwinia carotovora), potato common scab (Streptomyces scabiei), potato black leg disease (Pectobacterium carotovorum, Dickeia sp.), peach bacterial hole (Pseudomona syringae, Erwinia nigrifluens, Xanthomonas campestris), plum canker (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), corn Goss's wilt (Clavibacter michiganensis), Pierce's disease of grapes, olives, peaches, etc. (Xylella fastidiosa), and crown gall disease of Rosaceae plants such as apples, peaches, and cherries (Agrobacterium tumefaciens). ;

[0023] The method for controlling plant diseases of the present invention is carried out by applying an effective amount of the compound of the present invention or Composition A to plants or the soil in which the plants are grown. Examples of the application method include foliage application, soil application, and seed application.

[0024] The compound of the present invention or Composition A is typically formulated into aqueous suspensions, oil suspensions, oil solutions, emulsifiable concentrates, emulsions, microemulsions, microcapsule formulations, wettable powders, water dispersible granules, dusts, granules, tablets, aerosols, resin formulations, etc. by mixing an inert carrier such as a solid carrier, liquid carrier, or gaseous carrier with a surfactant, and optionally adding formulation adjuvants such as binders, dispersants, and stabilizers. In addition to these formulations, the compound of the present invention or Composition A can also be formulated into dosage forms described in the Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271 to 276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517. These formulations typically contain 0.0001 to 99% by weight of the compound of the present invention or Composition A.

[0025] Examples of solid carriers include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powder and granular chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0026] Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide (hereinafter referred to as DMSO), etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).

[0027] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide gas.

[0028] Examples of surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkyl sulfonates, alkylaryl sulfonates, alkyl sulfates, etc.).

[0029] Other formulation adjuvants include, for example, binders, dispersants, colorants, and stabilizers, and specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acid isopropyl phosphate, and dibutylhydroxytoluene.

[0030] In addition, adjuvants can be used as components that enhance or support the efficacy of the compound of the present invention. Specific examples include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).

[0031] In the present invention, the plant includes the whole plant, stems and leaves, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs, and seedlings.

[0032] Vegetative reproductive organs refer to plant roots, stems, leaves, and other parts that can grow when separated from the main body and placed in soil. Examples of vegetative reproductive organs include tuberous roots, creeping roots, bulbs, corms (or solid bulbs), tubers, rhizomes, stolons, rhizophores, cane cuttings, propagules, and vine cuttings. Stolons are sometimes called runners, and propagules are also called bulbils and are divided into broad buds and bulbils. Vines refer to shoots (a collective term for leaves and stems) of plants such as sweet potatoes and Japanese yams. Bulbs, corms, tubers, rhizomes, stem fragments, rhizophores, and tuberous roots are collectively called bulbils. Potato cultivation begins by planting tubers in the soil, and the tubers used are generally called seed potatoes.

[0033] Examples of the method for controlling plant diseases by applying an effective amount of the compound of the present invention or composition A to soil include a method of applying an effective amount of the compound of the present invention or composition A to soil before or after planting a plant. More specifically, for example, planting hole treatment (spraying in planting holes, mixing in planting hole treatment soil), plant base treatment (spraying in planting holes, mixing in plant base soil, plant base irrigation, plant base treatment in the latter half of the seedling raising period), planting furrow treatment (spraying in planting furrows, mixing in planting furrow soil), row treatment (row spraying, row soil mixing, row spraying in the growing season), row treatment at sowing (row spraying at sowing, mixing in row soil at sowing), overall treatment (overall soil spraying, overall soil mixing), side row treatment, water surface treatment (water surface application, water surface application after flooding), other soil spray treatments (foliar spraying of granules during the growing season, spraying under the crown or around the main trunk, soil surface spraying, soil surface mixing, seeding hole spraying, furrow surface spraying, spraying between plants), and others. Other irrigation treatments include soil irrigation, seedling irrigation, chemical injection treatment, ground level irrigation, chemical drip irrigation, chemigation), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding), seedling bed treatments (seedling bed spraying, seedling bed irrigation, water seedling bed spraying, seedling immersion), bed soil mixing treatments (bed soil mixing, bed soil mixing before sowing, spraying before soil covering at sowing, spraying after soil covering at sowing, covering soil mixing), and other treatments (hilling soil mixing, plowing in, topsoil mixing, rain-drop soil mixing, planting position treatment, granular inflorescence spraying, paste fertilizer mixing).

[0034] Seed treatments include, for example, treatment of seeds or vegetative reproductive organs with the compound of the present invention or Composition A. More specifically, examples include spray treatments in which a suspension of the compound of the present invention or Composition A is sprayed onto the surface of seeds or vegetative reproductive organs in a mist; smear treatments in which the compound of the present invention or Composition A is applied to seeds or vegetative reproductive organs; immersion treatments in which seeds or vegetative reproductive organs are immersed in a solution of the compound of the present invention or Composition A for a certain period of time; and methods of coating seeds or vegetative reproductive organs with a carrier containing the compound of the present invention or Composition A (film coating treatment, pellet coating treatment, etc.). Seed potatoes are particularly examples of the vegetative reproductive organs mentioned above. When applying Composition A to seeds or vegetative reproductive organs, Composition A can be applied to the seeds or vegetative reproductive organs as a single formulation, or different formulations of Composition A can be applied to the seeds or vegetative reproductive organs in multiple separate applications. Examples of methods for treating seeds or vegetative reproductive organs with multiple different formulations of Composition A include a method of treating seeds or vegetative reproductive organs with a formulation containing only the compound of the present invention as an active ingredient, air-drying the seeds or vegetative reproductive organs, and then treating with a formulation containing this ingredient; and a method of treating seeds or vegetative reproductive organs with a formulation containing both the compound of the present invention and this ingredient as active ingredients, air-drying the seeds or vegetative reproductive organs, and then treating with a formulation containing a component other than the component already treated. In the present invention, "seeds or vegetative reproductive organs carrying the compound of the present invention or Composition A" refers to seeds or vegetative reproductive organs to which the compound of the present invention or Composition A is attached. The seeds or vegetative reproductive organs carrying the compound of the present invention or Composition A may have materials other than the compound of the present invention or Composition A attached to them before or after the compound of the present invention or Composition A is attached to the seeds or vegetative reproductive organs. Furthermore, when Composition A is attached to the surface of the seeds or vegetative reproductive organs in layers, the layers may consist of one layer or multiple layers. Furthermore, when the layer consists of multiple layers, each layer may contain one or more active ingredients, or may consist of a layer containing one or more active ingredients and a layer containing no active ingredients. Seeds or vegetative reproductive organs carrying the compound of the present invention or composition A can be obtained, for example, by applying a formulation containing the compound of the present invention or composition A to seeds or vegetative reproductive organs by the seed treatment method described above.

[0035] The application rate of the compound of the present invention or Composition A varies depending on weather conditions, formulation, application time, application method, application location, target disease, target crop, etc., but in the case of foliage application or soil application, it is 2 The amount of the compound of the present invention or composition A is usually 1 g to 500 g per kg of seeds. In the case of seed treatment, the amount of the compound of the present invention or composition A is usually 0.001 g to 100 g per kg of seeds. When the compound of the present invention or composition A is formulated as an emulsifiable concentrate, wettable powder, flowable concentrate or the like, it is usually applied after being diluted with water so that the active ingredient concentration is 0.01 ppm to 10,000 ppm, and dusts, granules and the like are usually applied as they are.

[0036] The compound of the present invention or Composition A can be used as an agent for controlling plant diseases in agricultural lands such as fields, paddy fields, lawns, orchards, etc. Examples of plants include the following.

[0037] Corn (horse-tooth, hard grain, soft grain, explosive, glutinous, sweet, field corn), rice (long grain, short grain, medium grain, japonica, tropical japonica, indica, javanica, paddy rice, upland rice, floating rice, direct-seeded rice, transplanted rice, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, each winter wheat type, spring wheat type), barley (two-row barley (= beer barley), six-row barley, naked barley, waxy barley, each winter barley type, spring barley type), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (upland type, pima type), soybean (fully harvested seed varieties, edamame varieties, green-harvested varieties, indeterminate, determinate, semi-determinate types), peanuts, buckwheat, sugar beet (sugar production, animal feed, root vegetable, leafy vegetable, fuel), rapeseed (winter rapeseed type, spring rapeseed type), canola (winter canola type, spring canola type), sunflower (oil production, food, ornamental), sugarcane, tobacco, tea plant, mulberry, solanaceous vegetables (eggplant, tomato, bell pepper, chili pepper) , potatoes, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (leeks, onions, garlic, asparagus, etc.), Umbelliferae vegetables (carrots, parsley, celery, parsley, etc.), Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yams, scallions, Sweet potatoes, pome fruits (apples, European pears, Japanese pears, Chinese pears, quince, quince, etc.), stone fruits (peaches, plums, nectarines, plums, cherries, apricots, prunes, etc.), citrus fruits (Satsuma mandarins, oranges, lemons, limes, grapefruits, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates, coconuts, ornamental plants, forest plants,Turfgrass, pasture grass,

[0038] The above-mentioned plants are not particularly limited as long as they are varieties that are commonly cultivated, and include plants that can be produced by natural crossbreeding, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants that have been conferred resistance to herbicides such as HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or dicamba; plants that are capable of synthesizing selective toxins known to be found in the genus Bacillus, such as Bacillus thuringiensis; and plants that can be conferred specific insecticidal activity by synthesizing gene fragments that partially match endogenous genes derived from harmful insects and inducing gene silencing (RNAi; RNA interference) in the target harmful insect.

[0039] The present invention will be explained in more detail below with reference to production examples, formulation examples and test examples, but the present invention is not limited to these examples.

[0040] First, examples of the preparation of the compounds of the present invention are shown below.

[0041] 2-Methyl-[1,1'-biphenyl]-3-ol can be produced by the method described in U.S. Application Publication No. 2019 / 0016681.

[0042] Reference manufacturing example 1 To a mixture of 1.5 g of N,N-dimethylformamide, 0.50 g of 2-methyl-[1,1'-biphenyl]-3-ol, and 0.60 g of potassium carbonate, 0.40 g of methyl chloroacetate was added at room temperature, and the mixture was stirred at 50°C for 3 hours. At the same temperature, 2.0 g of xylene and 2.5 g of water were added to the resulting mixture, and the mixture was stirred and then separated. The resulting organic layer was cooled to room temperature, and 1.0 g of water was added, followed by separation. The resulting organic layer was concentrated under reduced pressure to obtain 0.62 g of methyl 2-((2-methyl-[1,1'-biphenyl]-3-yl)oxy)acetate (retention time 5.5 minutes under high-performance liquid chromatography analysis condition 1 below) as an oily substance.

[0043] [High-Performance Liquid Chromatography Analysis Condition 1] Mobile phase: Solution A: 0.1% trifluoroacetic acid aqueous solution, Solution B: acetonitrile Column: Shim-pack (registered trademark) XR-ODSII, 3.0 mm ID × 75 mm (Shimadzu Corporation) UV measurement wavelength: 254 nm Flow rate: 1.0 mL / min Column oven: 30°C Pump: LC-20AD (Shimadzu Corporation) x 2 (high-pressure gradient) Gradient conditions: Solution was delivered at the concentration gradient shown in [Table LC1].

[0044]

[0045] Reference manufacturing example 2 To a mixture of 3.00 g of xylene and 1.30 g of sodium methoxide, a mixture of 3.00 g of methyl 2-((2-methyl-[1,1'-biphenyl]-3-yl)oxy)acetate produced in accordance with the method described in Reference Production Example 1, 1.50 g of methyl formate, 6.00 g of tetrahydrofuran, and 3.00 g of xylene was added dropwise at 30°C over 1 hour. The resulting mixture was cooled to 10°C, and 9.00 g of water was added. 0.80 g of 35 wt% hydrochloric acid was added to the resulting mixture, and the mixture was separated to obtain 19.7 g of an aqueous layer containing sodium 3-methoxy-2-((2-methyl-[1,1'-biphenyl]-3-yl)oxy)-3-oxoprop-1-en-1-olate.

[0046] Production Example 1 To a mixture of 51.0 g of an aqueous layer containing sodium 3-methoxy-2-((2-methyl-[1,1'-biphenyl]-3-yl)oxy)-3-oxoprop-1-en-1-olate produced in accordance with the method described in Reference Production Example 2, 21.6 g of xylene, and 0.65 g of tetrabutylammonium bromide, 1.23 g of dimethyl sulfate was added at 25°C, and the mixture was stirred at 80°C for 20 hours. The resulting mixture was separated to obtain an organic layer containing the compound represented by formula (1) and the compound represented by formula (2). The resulting organic layer was concentrated under reduced pressure, and the concentrated mixture was purified by silica gel column chromatography (hexane / ethyl acetate solvent system) to obtain 1.42 g of the compound represented by formula (1) as a solid (retention time: 38.9 minutes under high performance liquid chromatography analysis condition 2 described below).

[0047] [High-performance liquid chromatography analysis conditions 2] Mobile phase: Solution A: 0.5 mM ammonium carbonate aqueous solution, Solution B: acetonitrile Column: XBridge™ Phenyl, particle size 3.5 μm, 4.6 mm I.D. × 150 mm (Waters) UV measurement wavelength: 250 nm Flow rate: 1.0 mL / min Column oven: 30°C Pump: LC-20AD (Shimadzu Corporation) x 2 (high-pressure gradient) Gradient conditions: Solution was delivered at the concentration gradient shown in [Table LC2].

[0048] The compound of formula (1) 1 The H-NMR values ​​are shown below. 1 H-NMR (DMSO-d6) δ: 7.54 (d, 2H), 7.44 (t, 2H), 7.36-7.33 (m, 2H), 7.27 (d, 1H), 7.19 (dd, 1H), 6.94 (d, 1H), 3.88 (s, 3H), 3.62 (s, 3H), 2.27 (s, 3H).

[0049] Next, examples of formulations of the compound of the present invention are shown below, where parts are by weight.

[0050] Formulation Example 1 20 parts of the compound of the present invention, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1:1), and 45 parts of water are mixed and processed using a pulverizer to obtain a formulation.

[0051] Formulation Example 2 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and silica (weight ratio 1:1), 10 parts of the compound of the present invention, and 55 parts of water are mixed and finely pulverized by wet pulverization to obtain a formulation.

[0052] Formulation Example 3 50 parts of the compound of the present invention, 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silica are ground and mixed to obtain a formulation.

[0053] Formulation Example 4 5 parts of the compound of the present invention, 9 parts of polyoxyethylene styrylphenyl ether, 5 parts of polyoxyethylene decyl ether (number of ethylene oxide added: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene are mixed to obtain a formulation.

[0054] Formulation Example 5 2 parts of the compound of the present invention, 1 part of silica, 2 parts of calcium lignosulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are pulverized and mixed, an appropriate amount of water is added, the mixture is kneaded, granulated in a granulator, and then dried to obtain a formulation.

[0055] Formulation Example 6 10 parts of the compound of the present invention is mixed with a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO, and 6.3 parts of GERONOL (registered trademark) TE250, 2.7 parts of Ethylan (registered trademark) NS-500LQ, and 54 parts of solvent naphtha are added thereto and mixed to obtain a formulation.

[0056] Furthermore, the plant disease control efficacy of the compound of the present invention is demonstrated by test examples. In Test Examples 1 to 9, the untreated plots refer to test plots conducted under the same conditions as those described in each test example, except that DMSO was dispensed instead of the DMSO dilution containing the compound of the present invention. In Test Examples 10 to 19, the untreated plots refer to plots in which foliage sprays of a water dilution of a formulation containing the compound of the present invention were not performed. In Test Examples 10 to 19, the formulated compound of the present invention refers to a formulation obtained by mixing 20 parts of the compound of the present invention, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1:1), and water to a total volume of 100 parts, and then processing the mixture using a grinder. In Test Examples 1 to 19, the compound of the present invention refers to the compound represented by formula (1) prepared according to the preparation method described in Preparation Example 1.

[0057] The YB liquid medium in Test Examples 2, 6, 7, 8 and 9 refers to a medium prepared by dissolving 10 g of yeast extract, 10 g of polypeptone and 20 g of sodium acetate (anhydrous) in 1 L of water and sterilizing the mixture.

[0058] Test Example 1: Control test against wheat leaf spot fungus (Septoria tritici) The compound of the present invention was diluted with DMSO to contain 150 ppm, and 1 μL was dispensed into a titer plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium) previously inoculated with spores of Septoria tritici was dispensed. The plate was incubated at 18°C ​​for 5 days to allow the wheat leaf spot fungus to grow. The absorbance at 550 nm in each well of the titer plate was measured, and this value was used as the growth rate of the wheat leaf spot fungus. As a result, the growth rate in the plots treated with the compound of the present invention was 50% or less of that in the untreated plot.

[0059] Test Example 2: Control test against cucumber Botrytis cinerea The compound of the present invention was diluted with DMSO to contain 150 ppm, and 1 μL of the diluted solution was dispensed into a titer plate (96 wells), followed by 150 μL of YB liquid medium inoculated with spores of Botrytis cinerea. The plate was incubated at 18° C. for 4 days to allow the Botrytis cinerea to grow, after which the absorbance at 550 nm of each well of the titer plate was measured, and this value was taken as the growth rate of Botrytis cinerea. As a result, the growth rate in the plots treated with the compound of the present invention was 50% or less of that in the untreated plot.

[0060] Test Example 3: Control test against Ustilago maydis The compound of the present invention was diluted with DMSO to a concentration of 150 ppm, and 1 μL was dispensed into a titer plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium) previously inoculated with spores of Ustilago maydis was dispensed. The plate was incubated at 18°C ​​for 4 days to allow the Ustilago maydis to grow. The absorbance at 550 nm of each well of the titer plate was then measured, and this value was used as the growth rate of Ustilago maydis. As a result, the growth rate in the plots treated with the compound of the present invention was 50% or less of that in the untreated plot.

[0061] Test Example 4: Control test against barley scald fungus (Rhynchosporium secalis) The compound of the present invention was diluted with DMSO to contain 150 ppm, and 1 μL was dispensed into a titer plate (96 wells), followed by 150 μL of potato decoction liquid medium (PDB medium) previously inoculated with spores of barley scald fungus. The plate was incubated at 18° C. for 7 days to allow the barley scald fungus to grow, and the absorbance at 550 nm of each well of the titer plate was measured, and this value was taken as the growth rate of the barley scald fungus. As a result, the growth rate in the plots treated with the compound of the present invention was 50% or less of the growth rate in the untreated plot.

[0062] Test Example 5: Control test against Pythium ultimum The compound of the present invention was diluted with DMSO to contain 150 ppm, and 1 μL was dispensed into a titer plate (96 wells), followed by 150 μL of potato decoction liquid medium (PDB medium) previously inoculated with spores of Pythium ultimum. The plate was incubated at 23° C. for 5 days to allow the Pythium ultimum to grow, after which the absorbance at 550 nm of each well of the titer plate was measured, and this value was taken as the growth rate of Pythium ultimum. As a result, the growth rate in the plots treated with the compound of the present invention was 50% or less of that in the untreated plot.

[0063] Test Example 6: Control test against peach scab fungus (Cladosporium carpophilum) The compound of the present invention was diluted with DMSO to contain 1500 ppm, and 1 μL of the diluted solution was dispensed into a titer plate (96 wells), followed by 150 μL of YB liquid medium inoculated with spores of peach scab fungus. The plate was incubated at 18° C. for 5 days to allow the peach scab fungus to grow, and the absorbance at 550 nm of each well of the titer plate was measured, and this value was taken as the growth rate of the peach scab fungus. As a result, the growth rate in the plots treated with the compound of the present invention was 50% or less of that in the untreated plot.

[0064] Test Example 7: Control test against peach scab fungus (Cladosporium carpophilum) The compound of the present invention was diluted with DMSO to contain 150 ppm, and 1 μL of the diluted solution was dispensed into a titer plate (96 wells), followed by 150 μL of YB liquid medium inoculated with spores of peach scab fungus. The plate was incubated at 18° C. for 5 days to allow the peach scab fungus to grow, and the absorbance at 550 nm of each well of the titer plate was measured, and this value was taken as the growth rate of the peach scab fungus. As a result, the growth rate in the plots treated with the compound of the present invention was 50% or less of that in the untreated plot.

[0065] Test Example 8: Control test against Cochliobolus miyabeanus The compound of the present invention was diluted with DMSO to a concentration of 1500 ppm, and 1 μL of the diluted solution was dispensed into a titer plate (96 wells), followed by 150 μL of YB liquid medium inoculated with spores of Cochliobolus miyabeanus. The plate was incubated at 23° C. for 3 days to allow the Cochliobolus miyabeanus to grow. The absorbance at 550 nm in each well of the titer plate was then measured, and this value was taken as the growth rate of the Cochliobolus miyabeanus. As a result, the growth rate in the plots treated with the compound of the present invention was 50% or less of that in the untreated plot.

[0066] Test Example 9: Control test against Cochliobolus miyabeanus The compound of the present invention was diluted with DMSO to contain 150 ppm, and 1 μL of the diluted solution was dispensed into a titer plate (96 wells), followed by 150 μL of YB liquid medium inoculated with spores of Cochliobolus miyabeanus. The plate was incubated at 23° C. for 3 days to allow the Cochliobolus miyabeanus to grow. The absorbance at 550 nm in each well of the titer plate was then measured, and this value was taken as the growth rate of the Cochliobolus miyabeanus. As a result, the growth rate in the plots treated with the compound of the present invention was 50% or less of that in the untreated plot.

[0067] Test Example 10: Control test against wheat leaf blight (Septoria tritici) Plastic pots were filled with soil, and wheat (cultivar: Apogee) was sown therein and cultivated in a greenhouse for 10 days. A formulated compound of the present invention was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the foliage of the wheat so that sufficient adhesion was achieved on the leaf surfaces. After spraying, the wheat was air-dried, and four days later, an aqueous suspension containing spores of the wheat leaf blight fungus was sprayed and inoculated. After inoculation, the wheat was placed under humid conditions at 18°C ​​for three days, and then cultivated under light for 14 to 18 days, after which the lesion area was examined. As a result, the lesion area on the wheat treated with the compound of the present invention was 30% or less of that on the untreated wheat.

[0068] Test Example 11: Control test against wheat leaf blight (Septoria tritici) Soil was filled into plastic pots, wheat (cultivar: Apogee) was sown therein, and the plants were grown in a greenhouse for 10 days. An aqueous suspension of spores of the wheat leaf blight fungus was sprayed and inoculated. After inoculation, the wheat plants were placed under humid conditions at 18°C ​​for 3 days. A formulated compound of the present invention was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the stems and foliage of the wheat plants so that the compound adhered sufficiently to the leaf surfaces. After spraying, the wheat plants were air-dried and placed under light for 14 to 18 days, after which the lesion area was examined. As a result, the lesion area on the wheat plants treated with the compound of the present invention was 30% or less of that on the untreated wheat plants.

[0069] Test Example 12: Control test against wheat rust (Puccinia recondita) Plastic pots were filled with soil, and wheat (cultivar: Shirogane) was sown therein and cultivated in a greenhouse for 9 days. The formulated compound of the present invention was mixed with water to a concentration of 800 ppm, and the resulting mixture was sprayed on the stems and foliage of the wheat so that it adhered well to the leaf surface. After spraying, the wheat was air-dried and cultivated at 20°C under illumination for 5 to 7 days, after which it was inoculated with wheat rust spores by sprinkling. After inoculation, the wheat was placed at 23°C under dark and humid conditions for 1 day, and then cultivated at 20°C under illumination for 8 days, and the lesion area was examined. As a result, the lesion area in the wheat treated with the compound of the present invention was 30% or less of that in the untreated wheat.

[0070] Test Example 13: Control test against wheat rust (Puccinia recondita) Plastic pots were filled with soil, and wheat (cultivar: Shirogane) was sown therein and cultivated in a greenhouse for 9 days. A formulated compound of the present invention was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the foliage of the wheat so that sufficient adhesion was achieved on the leaf surface. After spraying, the wheat was air-dried and cultivated at 20°C under illumination for 5 to 7 days, after which spores of wheat rust fungus were sprinkled on and inoculated. After inoculation, the wheat was placed at 23°C under dark and humid conditions for 1 day, and then cultivated at 20°C under illumination for 8 days, and the lesion area was examined. As a result, the lesion area on the wheat treated with the compound of the present invention was 30% or less of that on the untreated wheat.

[0071] Test Example 14: Control test against barley net blotch (Pyrenophora teres) Plastic pots were filled with soil, and barley (variety: Nishinohoshi) was sown therein and cultivated in a greenhouse for 7 days. A formulated compound of the present invention was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the foliage of the barley so that sufficient adhesion was achieved on the leaf surfaces. After spraying, the barley was air-dried, and one day later, an aqueous suspension of spores of Pyrenophora teres pv. hordei was sprayed and inoculated. After inoculation, the barley was placed under humid conditions in a greenhouse at 23°C during the day and 20°C at night for 3 days, and then cultivated in the greenhouse for 7 days, after which the lesion area was examined. As a result, the lesion area in the barley treated with the compound of the present invention was 30% or less of that in the untreated barley.

[0072] Test Example 15: Control test against tomato ring rot (Alternaria solani) Soil was filled into plastic pots, tomatoes (variety: Patio) were sown therein, and the plants were cultivated and grown in a greenhouse for 20 days. A formulated compound of the present invention was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the stems and leaves of the tomatoes so that sufficient adhesion was achieved on the leaf surfaces. After spraying, the tomatoes were air-dried, and one day later, they were inoculated by spraying with an aqueous suspension of spores of the tomato ring rot fungus. After inoculation, the tomatoes were kept at 18°C ​​under humid conditions for 6 days, and the lesion area was then examined. As a result, the lesion area on the tomatoes treated with the compound of the present invention was 30% or less of that on the untreated tomatoes.

[0073] Test Example 16: Control test against soybean rust (Phakopsora pachyrhizi) Soil was filled into plastic pots, and soybeans (cultivar: Kurosengoku) were sown and grown in a greenhouse for 10 to 14 days. A formulated compound of the present invention was mixed with water to a concentration of 800 ppm, and the resulting mixture was sprayed on the stems and foliage of the soybeans so that sufficient adhesion was achieved on the leaf surface. After spraying, the soybeans were air-dried, and 2 to 5 days later, they were inoculated by spraying with an aqueous suspension of soybean rust spores. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under humid conditions for 1 to 2 days, and then cultivated in the greenhouse for 10 to 14 days, after which the lesion area was examined. As a result, the lesion area on soybeans treated with the compound of the present invention was less than 30% of that on untreated soybeans.

[0074] Test Example 17: Control test against soybean rust (Phakopsora pachyrhizi) Soil was filled into plastic pots, and soybeans (cultivar: Kurosengoku) were sown and grown in a greenhouse for 10 to 14 days. A formulated compound of the present invention was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the stems and foliage of the soybeans so that sufficient adhesion was achieved on the leaf surface. After spraying, the soybeans were air-dried, and 2 to 5 days later, they were inoculated by spraying with an aqueous suspension of soybean rust spores. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under humid conditions for 1 to 2 days, and then cultivated in the greenhouse for 10 to 14 days, after which the lesion area was examined. As a result, the lesion area on soybeans treated with the compound of the present invention was less than 30% of that on untreated soybeans.

[0075] Test Example 18: Control test against soybean rust (Phakopsora pachyrhizi) Soil was filled into plastic pots, soybeans (cultivar: Kurosengoku) were sown therein, and the plants were cultivated in a greenhouse for 10 days. An aqueous suspension containing soybean rust spores was then sprayed and inoculated. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under humid conditions for 1 day, and then cultivated in the greenhouse for 2 days. After that, the formulated compound of the present invention was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the stems and leaves of the soybeans so that it adhered well to the leaf surface. After spraying, the soybeans were air-dried and cultivated in a greenhouse for 8 days, and the lesion area was then examined. As a result, the lesion area on the soybeans treated with the compound of the present invention was less than 30% of that on the untreated soybeans.

[0076] Test Example 19: Control test against soybean spot disease (Cercospora sojina) Soybeans (variety: Tachinagaha) were filled into plastic pots with soil, sown therein, and cultivated in a greenhouse for 13 days. An aqueous suspension of Cercospora sojina spores was then sprayed and inoculated. After inoculation, the soybeans were placed in a humid greenhouse at 23°C for 4 days and then cultivated in a greenhouse at 23°C for 1 day. After that, the formulated compound of the present invention was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed on the stems and leaves of the soybeans so that it adhered well to the leaf surface. After spraying, the soybeans were air-dried and cultivated in a greenhouse at 24°C during the day and 20°C at night for 21 days, and then the lesion area was examined. As a result, the lesion area on the soybeans treated with the compound of the present invention was 30% or less of that on the untreated soybeans.

[0077] The compound of the present invention has an excellent controlling effect against plant diseases and is useful as an active ingredient of a composition for controlling plant diseases.

Claims

1. Formula (A) A compound represented by the formula:

2. A composition for controlling plant diseases, comprising the compound according to claim 1 and an inert carrier.

3. A composition containing one or more components selected from the group consisting of groups (a), (b), (c) and (d), and the compound described in claim 1: Group (a): a group consisting of insecticidal active components, acaricidal active components and nematicidal active components; Group (b): fungicidal active components; Group (c): plant growth regulator components; Group (d): repellent components.

4. A method for controlling plant diseases by applying an effective amount of the compound described in claim 1, an effective amount of the composition for controlling plant diseases described in claim 2, or an effective amount of the composition described in claim 3 to a plant or the soil in which the plant is grown.

5. Use of the compound according to claim 1, the composition for controlling plant diseases according to claim 2, or the composition according to claim 3 for controlling plant diseases.

6. A seed or vegetative reproductive organ carrying an effective amount of the compound according to claim 1, an effective amount of the composition for controlling plant diseases according to claim 2, or an effective amount of the composition according to claim 3.

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