RU2769764C2 - Use of an acyclic picolinamide compound as a fungicide for controlling phytopathogenic fungi in vegetable crops - Google Patents

Abstract

FIELD: agriculture.

SUBSTANCE: method of controlling fungal diseases in vegetable crops selected from pumpkin plants, tomatoes, leafy vegetables, potatoes, pepper plants and garden beans, includes the steps of bringing at least a part of the plant and/or the area adjacent to the plant into contact with a compound I or a composition containing a compound I:

EFFECT: proposed method of controlling fungal diseases in vegetable crops is effective against fungal pathogens selected from a group, consisting of agents of black spotted cabbage leaves (Alternaria brassicicola), lettuce Sclerotinia (Sclerotinia sclerotiorum), hot pepper anthracnose (Colletotrichum capsici), tomato leaf mold (Mycovellosiella fulva), watermelon black rot (Stagonosporopsis cucurbitacearum), garden bean gray rot (Botrytis cinerea), tomato target spot (Corynespora cassiicola) and tomato anthracnose (Colletotrichum coccodes).

1 cl, 7 tbl

Description

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims priority under U.S. Provisional Application No. 62/500172, filed May 2, 2017, which is expressly incorporated herein by reference.

FIELD OF THE INVENTION

[0002] The present invention relates to the use of ( S )-1,1-bis(4-fluorophenyl)propan-2-yl-(3-acetoxy-4-methoxypicolinoyl) -L -alaninate for the control of fungal diseases in vegetable crops.

BACKGROUND AND BRIEF DESCRIPTION OF THE INVENTION

[0003] Fungicides are compounds of natural or synthetic origin that act to protect and treat plants from damage caused by agriculturally important fungi. In general, there is no one fungicide suitable for all situations. Consequently, research is ongoing to obtain fungicides that may have improved performance, are easier to apply, and cost less.

[0004] The present invention relates to ( S )-1,1-bis(4-fluorophenyl)propan-2-yl-(3-acetoxy-4-methoxypicolinoyl) -L -alaninate (compound I) and its use as a fungicide . Compound I can provide protection against ascomycetes, basidiomycetes and deuteromycetes.

[0005] One embodiment of the present invention includes a method of controlling disease caused by a pathogen in a plant that is at risk of disease from the pathogen, comprising contacting the plant, or an area adjacent to the plant, with a composition containing Compound I.

[0006] Another embodiment of the present invention is the use of Compound I for protecting a plant from being attacked by a phytopathogenic organism or treating a plant infected with a phytopathogenic organism, comprising applying Compound I or a composition containing Compound I to soil, plant, plant part, foliage and /or seeds.

[0007] In addition, another embodiment of the present invention is a composition useful for protecting a plant from attack by a phytopathogenic organism and/or treating a plant infected with a phytopathogenic organism, comprising Compound I and a plant-acceptable carrier material.

DETAILED DESCRIPTION

[0008] One illustrative embodiment of the present invention includes a mixture for controlling the growth of fungi, and the mixture contains compound I:

[0009] The Compound I of the present invention can be applied using any of a number of known techniques either as Compound I or as formulations containing Compound I. For example, Compound I can be applied to roots, stems, seeds, flowers, or foliage of plants for the control of various fungi without compromising the industrial value of plants. Compound I can also be used as a foliar spray, soil spray, soil dressing, irrigation water application, soil irrigation, soil injection or seed treatment. The material can be used in the form of any of the commonly used formulation types, for example, solutions, powdered formulations, wettable powders, flowable concentrates, or emulsifiable concentrates.

[0010] Preferably, Compound I of the present invention is used in the form of a formulation comprising Compound I with a plant-acceptable carrier. Concentrated formulations may be dispersed in water or other liquids for use, or the formulations may be dusted or granular and may then be applied without further processing. The compositions can be obtained according to procedures that are conventional in the field of agrochemicals.

[0011] The present invention contemplates all media with which Compound I can be formulated for delivery and use as a fungicide. Typically, the formulations are used in the form of aqueous suspensions or emulsions. Such suspensions or emulsions can be prepared from water-soluble, water-suspendable or emulsifiable formulations, which are solids commonly known as wettable powders; or liquids commonly known as emulsifiable concentrates, aqueous suspensions or suspension concentrates. It is readily understood that any material to which Compound I can be added can be used, as long as it provides the desired benefit without significantly impairing Compound I's antifungal activity.

[0012] Wettable powders that can be compressed into water-dispersible granules contain a thoroughly mixed mixture containing Compound I, an inert carrier, and surfactants. The concentration of Compound I in the wettable powder may be from about 10 percent to about 90 percent by weight, based on the total weight of the wettable powder, more preferably from about 25 percent to about 75 percent by weight. When formulated as wettable powders, Compound I may be formulated with any fine solid such as prophyllite, talc, chalk, gypsum, fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clays, diatomaceous earth, purified silicates, or similar. In such operations, the finely dispersed carrier and surfactants are usually mixed with compound I and crushed.

[0013] Compound I emulsifiable concentrates may contain a suitable concentration, such as from about 10 weight percent to about 50 weight percent Compound I, in a suitable liquid, based on the total weight of the concentrate. Compound I can be dissolved in an inert carrier which is either a water-miscible solvent or a mixture of water-immiscible organic solvents and emulsifiers. The concentrates can be diluted with water and oil to give spray mixtures in the form of oil-in-water emulsions. Suitable organic solvents include aromatics, in particular high boiling naphthalene and olefinic petroleum fractions such as heavy aromatic naphtha. Other organic solvents may also be used, for example terpene solvents including rosin derivatives, aliphatic ketones such as cyclohexanone, and complex alcohols such as 2-ethoxyethanol.

[0014] Emulsifiers that can be preferably used herein can be easily determined by those skilled in the art and include various nonionic, anionic, cationic, and amphoteric emulsifiers, or a mixture of two or more emulsifiers. Examples of nonionic emulsifiers useful in the preparation of emulsifiable concentrates include polyalkylene glycol ethers and condensation products of alkyl and arylphenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as ethoxylated alkylphenols and carboxylic acid esters solubilized with a polyol or polyoxyalkylene. . Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include oil-soluble salts (eg, calcium) of alkylarylsulfonic acids, oil-soluble salts or sulfated polyglycol ethers, and the corresponding salts of a phosphated polyglycol ether.

[0015] Typical organic liquids that can be used in the preparation of the emulsifiable concentrates of Compound I of the present invention are aromatic liquids such as xylene, propylbenzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; various fatty acid dialkylamides, in particular fatty glycol dimethylamides and glycol derivatives such as n- butyl ether, diethylene glycol ethyl ether or methyl ether and triethylene glycol methyl ether and the like. Mixtures of two or more organic liquids may also be used in the preparation of an emulsifiable concentrate. Organic liquids include xylene and propylbenzene fractions, with xylene being most preferred in some instances. Surface active dispersants are typically used in liquid formulations and in amounts of 0.1 to 20 percent by weight, based on the total weight of the dispersant with Compound I. The formulations may also contain other compatible additives such as plant growth regulators and other biologically active agents. compounds used in agriculture.

[0016] Aqueous suspensions containing compound I can be dispersed in an aqueous medium at a concentration in the range of from about 5 to about 50 percent by weight, based on the total weight of the aqueous suspension. Suspensions are prepared by finely grinding Compound I and vigorously mixing the ground material with a medium of water and surfactants selected from the same types discussed above. Other components such as inorganic salts and synthetic or natural gums can also be added to increase the density and viscosity of the aqueous medium.

[0017] Compound I can also be applied as a granular formulation, which is particularly suitable for soil application. Granular formulations typically contain from about 0.5 to about 10 percent by weight, based on the total weight of the Compound I granular formulation, dispersed in an inert carrier that consists entirely or in large part of coarse inert material such as attapulgite, bentonite, diatomite, clay , or a similar inexpensive substance. Such formulations are typically prepared by dissolving Compound I in a suitable solvent and applying it to a granular carrier that has been preformed into appropriately sized particles ranging from about 0.5 mm to about 3 mm. A suitable solvent is one in which Compound I is substantially or completely soluble. Such formulations can also be prepared by making a dough or paste from the carrier, compound I and solvent, and then crushing and drying to obtain the desired granular particle size.

[0018] Pulverized formulations containing Compound I can be prepared by intimately mixing Compound I in powder form with a suitable pulverized agricultural carrier such as, for example, kaolin clay, ground vulcanite, and the like. Pulverized formulations may suitably contain from about 1 to about 10 percent by weight of Compound I, based on the total weight of the pulverulent formulation.

[0019] the Formulations may additionally contain auxiliary surfactants to enhance the deposition, wetting and penetration of the compound I into the target culture and organism. These co-surfactants may optionally be used as a formulation component or as a tank mix. The amount of co-surfactant will typically range from 0.01 to 1.0 percent by volume, based on the volume of water sprayed, preferably from 0.05 to 0.5 percent by volume. Suitable co-surfactants include, without limitation, ethoxylated nonylphenols, ethoxylated synthetic or natural alcohols, ester or sulfosuccinic acid salts, ethoxylated organosilicones, ethoxylated fatty amines, and mixtures of surfactants with mineral or vegetable oils. The formulations may also contain oil-in-water emulsions such as those disclosed in US Patent Application Serial No. 11/495,228, the disclosure of which is specifically incorporated herein by reference.

[0020] In some instances, it will be advantageous to spray Compound I formulations via aerial application using airplanes or helicopters. The specific components of these aerial formulations depend on the crop being treated. Aerial application formulations for vegetable crops are applied with a spray volume of preferably 15 to 50 liters per hectare (l/ha) with standard types of wetting, sticking, spreading or penetrating surfactants such as non-ionic surfactants , organosilicones or crop oil concentrates, preferably 0.05 to 15 percent based on the volume of water to be sprayed.

[0021] The compositions may optionally contain combinations that contain other pesticidal compounds. Such additional pesticidal compounds may be fungicides, insecticides, herbicides, nematicides, miticides, arthropodicides, bactericides, additives such as nonionic surfactants, organosilicones and crop oils, or combinations thereof, which are compatible with the compounds of the present invention in the media. selected for use and do not interfere with the activity of the compounds of the present invention. Therefore, in such embodiments, another pesticidal compound is used as an additional toxicant for the same or different pesticidal application. The compound I and the pesticidal compound in combination may generally be in a weight ratio of from 1:100 to 100:1.

[0022] the Compound I of the present invention can also be combined with other fungicides to obtain fungicidal mixtures and synergistic mixtures based on them. Compound I of the present invention is often used in conjunction with one or more other fungicides to control a wider range of undesirable diseases. When used in conjunction with other fungicide(s), Compound I herein claimed can be formulated with other fungicide(s), tank mixed with other fungicide(s), or applied sequentially with other fungicide(s). Such other fungicides may include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, amethoctradin, amisulbrom, antimycin,Ampelomyces quisqualis, aconazole, azoxystrobin,Bacillus subtilis,Bacillus subtilis, strain QST713, benalaxyl, benomyl, benthiavalicarb-isopropyl, benzyl aminobenzenesulfonate salt (BABS), bicarbonates, biphenyl, bismertiazole, bitertanol, bixafen, blasticidin-S, borax, Bordeaux liquid, boscalid, bromuconazole, bupirimate, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamide, carvone, chlazafenone, chloroneb, chlorthalonil, chlosolinate,Coniothyrium minitans, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), copper (I) oxide, cyazofamide, cyflufenamide, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, ethylene bis-(dithiocarbamate) diammonium, dichlofluanid, dichlorophen, diclocimet, diclomesin, dichloran, dietofencarb, difenoconazole, diphenzoquat ion, diflumetorim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, diphenylamine, dithianone, dodemorph, dodemorphacetate, dodin, dodine free base, edifenphos, enestrobin, enestroburin, epoxiconazole, ethoboxam, ethoxyquin, etridiasol, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidine, fenpropimorph, fenpyrazamine, fentin, fentinacetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph, fluopicolide, fluopyram, fluorimide, fluoxastrobin, fluquinconazole, fluzilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapiroxad, folpet, formaldehyde, fosetil, fosetil-aluminum furametpyr, guasatin, guasatin acetates, GY-81, hexachlorobenzene, hexaconazole, hymexazole, imazalil, imazalyl sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine-tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalilane, isopyrazamylcarb, isoprothiolan , kasugamycin, kasugamycin hydrochloride hydrate, kresoxim-methyl, laminarin, mancopper, mancose b, mandipropamide, maneb, mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercuric dichloride, mercuric oxide, mercuric chloride, metalaxyl, metalaxyl-M, metam, metam-ammonium, metam-potassium, metam-sodium, metconazole, metasulfocarb, methyl iodide , methylisothiocyanate, metiram, methominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrotal-isopropyl, nuarimol, octilinone, ofuras, butyric acid (fatty acids), orysastrobin, oxadixyl, oxin-copper, oxpoconazole fumarate, oxycarboxine, pefurazoate, penconazole, pencicuron, penflufen, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercuric acetate, phosphonic acid, phthalide, picoxystrobin, polyoxin B, polyoxins, polyoxorim, sodium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriophenone, pyroquilon, quinoc lamin, quinoxifene, quintozen, extractReynoutria sachalinensis, sedaxan, silthiopham, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, tar oils, tebuconazole, tebufloquine, teknazen, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, thiadinil, tolclofos -methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizol, triforin, triphenyltin hydroxide, triticonazole, validamycin, valifenalate, valifenal, vinclozolin, zineb, ziram, zoxamide,candida oleophila,Fusarium oxysporum,Gliocladium spp.,Phlebiopsis gigantea,Streptomyces griseoviridis,Trichoderma spp., (RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide, 1,2-dichloropropane, 1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate, 1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitropropane, 2-(2-heptadecyl-2-imidazolin-1-yl)ethanol, 2,3-dihydro-5-phenyl-1,4-dithiine 1,1,4,4-tetraoxide, 2-methoxyethylmercury acetate, 2-methoxyethylmercury chloride, 2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop-1-enyl)phenylthiocyanatem, aminopyrifene, ampropylphos, anilazine, azithiram, barium polysulfide , Bayer 32394, benodanil, benquinox, bentaluron, benzamacryl; benzamacryl isobutyl, benzamorph, benzovindiflupyr, binapacryl, bis(methylmercury)sulfate, bis(tributyltin)oxide, butiobate, cadmium-calcium-copper-zinc chromate-sulfate, carbamorph, CECA, chlobentiazone, chloraniformmethane, chlorphenazole, chlorquinox, climbazole, bis (3-phenylsalicylate) copper, copper-zinc chromate, cumoxystrobin, kufraneb, copper hydrazinium sulfate, cuprobam, cyclafuramide, cypendazole, cyprofuram, decafentine, dichlobentiazox, dichlon, dichlozoline, diclobutrazol, dimethirimol, dinoctone, dinosulfone, dinoterbone, dipimethitron, dipyrithione, dithalymphos, dodicin, drazoxolone, EBP, enoxastrobin, ESBP, etaconazole, etem, etirim, phenaminosulf, fenaminstrobin, fenapanil, fenitropan, fenpicoxamide, fluindapir, fluopimomide, fluotrimazole, flufenoxystrobin, furcarbanil, furconazole, furconazole-cis, furmecyclox, furmecyclox, griseofulvin, galacrinate, Hercules 3944, hexylthiophos, ICIA0858, inpirfluxam, ipfentrifluconazole, ipflufenoquin, isofetamide, isoflucypram, isopamphos, isovaledion, mandestrobin, m ebenil, mecarbinzid, mefentrifluconazole, metazoxolone, metfuroxam, methylmercury dicyandiamide, metsulfowax, methyltetraprol, milneb, mucochlorous anhydride, myclozolin,N-3,5-dichlorophenylsuccinimide,N-3-nitrophenylitaconimide, natamycin,N-ethylmercury-4-toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), OCH, oxathiapiproline, phenylmercury dimethyldithiocarbamate, phenylmercury nitrate, phosdifene, picarbutrazox, prothiocarb; hydrochloride protiokarba, pidiflumetofen, pirakarbolid, pirapropoin, piraziflumid, piridahlometil, piridinitril, pirizoksazol, piroksihlor, piroksifur, kvinatsetol, kvinatsetolsulfat, kvinazamid, kvinkonazol, kvinofumelin, rabenzazol, salicylanilide, SSF-109, sultropen, Tekor, tiadifluor, titsiofen, tiohlorfenfim, thiophanate , thioquinox, thioximide, triamiphos, triarimol, triazbutyl, trichlamide, triclopyricarb, triflumesopyrim, urbacid, sarilamide, and any combination thereof.

[0023] In addition, the compound I of the present invention can be combined with other pesticides, including insecticides, nematocides, miticides, arthropodicides, bactericides, or combinations thereof, which are compatible with the compound I of the present invention in the medium chosen for application and do not interfere with the activity compounds I, to obtain pesticide mixtures and their synergistic mixtures. Compound I of the present invention can be used in conjunction with one or more other pesticides to control a wider range of unwanted pests. When used in conjunction with other pesticides, Compound I as claimed herein may be formulated with other pesticide(s), tank mixed with other pesticide(s), or applied sequentially with other pesticide(s). (s). Exemplary insecticides include, but are not limited to, antibiotic-based insecticides such as allosamidin and thuringiensin; insecticides based on macrocyclic lactones , such as spinosad and spinetoram; avermectin-based insecticides such as abamectin, doramectin, emamectin, eprinomectin, ivermectin and selamectin; milbemycin insecticides such as lepimectin, milbemectin, milbemycin oxime and moxidectin; carbamate-based insecticides such as bendiocarb and carbaryl; benzofuranylmethylcarbamate insecticides such as benfuracarb, carbofuran, carbosulfan, decarbofuran and furatiocarb; insecticides based on dimethylcarbamates : dimitan, dimethylan, hiquincarb and pyrimicarb; oximcarbamate insecticides such as alanicarb, aldicarb, aldoxycarb, butocarboxym, butoxycarboxym, methomyl, nitrilacarb, oxamyl, tazimcarb, thiocarboxym, thiodicarb and thiophanox; phenylmethylcarbamate-based insecticides such as allixicarb, aminocarb, bufencarb, butacarb, carbanolate, cloetocarb, dicrezyl, dioxacarb, EMPC, ethiofencarb, fenetacarb, fenobucarb, isoprocarb, methiocarb, metolacarb, mexacarbate, promacyl, promecarb, propoxylcarb, xylmethacarb, trimethocarb ; drying insecticides such as boric acid, diatomaceous earth and silica gel; diamide -based insecticides such as broflanilide, chloranthraniliprole, cyantraniliprole, cyclaniliprole, cyhalodiamide, flubendiamide, tetrachloranthraniliprole and tetraniliprole; diarylisoxazoline-based insecticides such as fluxametamide; dinitrophenol-based insecticides : dinex, dinoprop, dinosam and DNOC; fluorine-containing insecticides such as barium hexafluorosilicate, cryolite, sodium fluoride, sodium hexafluorosilicate and sulfluramide; formamidine-based insecticides such as amitraz, chlordimeform, formetanate and formparanate; respiratory insecticides such as acrylonitrile, carbon disulfide, carbon tetrachloride, chloroform, chloropicrin, para-dichlorobenzene, 1,2-dichloropropane, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, hydrogen cyanide, iodomethane, methyl bromide, methyl chloroform, methylene chloride, naphthalene, phosphine, sulfuryl fluoride and tetrachloroethane; inorganic insecticides such as borax, calcium polysulfide, copper oleate, mercury(I) chloride, potassium thiocyanate, and sodium thiocyanate; chitin synthesis inhibitors such as bistrifluron, buprofezin, chlorfluazuron, cyromazine, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron and triflumuron; juvenile hormone mimics such as epofenonan, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxyfen, and triprene; juvenile hormones such as juvenile hormone I, juvenile hormone II, and juvenile hormone III; mesoionic insecticides such as dichloromesothiasis and triflumesopyrim; moulting hormone agonists such as cromafenoside, halofenoside, methoxyfenoside and tebufenoside; moulting hormones such as α-ecdysone and ecdysterone; shedding inhibitors such as diofenolan; precocenes , such as precocene I, precocene II, and precocene III; unclassified insect growth regulators such as dicyclanil; non-reistoxin analog insecticides such as bensultap, cartap, thiocyclam and thiosultap; pyridylpyrazole -based insecticides such as ticlopirazoflor; nicotinoid-based insecticides , such as flonicamid; nitroguanidine-based insecticides such as clothianidin, dinotefuran, imidacloprid and thiamethoxam; nitromethylene-based insecticides , such as nitenpyram and nithiazine; pyridylmethylamine insecticides such as acetamiprid, cycloxapride, imidacloprid, nitenpyram and thiacloprid; organochlorine insecticides such as bromine-DDT, camphechlor, DDT, pp′-DDT, ethyl-DDD, HCH, gamma-HCH, lindane, methoxychlor, pentachlorophenol, and TDE; cyclodiene insecticides such as aldrin, bromocyclene, chlorbicyclene, chlordane, chlordecone, dieldrin, dilor, endosulfan, alpha-endosulfan, endrin, HEOD, heptachlor, HHDN, isobenzane, isodrin, kelevan and mirex; organophosphorus insecticides such as bromfenvinphos, chlorphenvinphos, crotoxyphos, dichlorvos, dicrotophos, dimethylvinphos, fospirate, heptenophos, methocrotophos, mevinphos, monocrotophos, naled, naphtalophos, phosphamidon, propafos, TEPP, and tetrachlorvinphos; organothiophosphorus insecticides such as dioxabenzophos, phosmethylan and phentoate; aliphatic organothiophosphorus insecticides such as acetion, amiton, cadusafos, chlorethoxyphos, chlormephos, demefion, demefion-O, demefion-S, demeton, demeton-O, demeton-S, demeton-methyl, demeton-O-methyl, demeton-S- methyl, demetone-S-methylsulfone, disulfotone, ethion, etoprofos, IPSP, isothioate, malathion, methacryphos, oxydemeton-methyl, oxydeprofos, oxydisulfotone, phorate, sulfotep, terbuphos and thiometon; aliphatic amide-based thiophosphorus insecticides such as amidithione, cyantoate, dimethoate, etoate-methyl, formotion, mecarbam, omethoate, protoate, sofamide, and vamidothione; oxime-based thiophosphorus insecticides such as chlorfoxim, phoxim and phoxim-methyl; heterocyclic organothiophosphorus insecticides such as azamethifos, coumaphos, cumitoate, dioxathion, endothion, menason, morphothion, phosalone, pyraclophos, pyridafenthion and quinothion; benzothiopyran-based thiophosphorus insecticides such as ditycrophos and tycrophos; benzotriazine-based organophosphorus insecticides such as azinphos-ethyl and azinphos-methyl; thiophosphorus-organic insecticides based on isoindoles , such as dialyphos and phosmet; thiophosphorus organic insecticides based on isoxazoles , such as isoxathion and zolaprofos; pyrazolopyrimidine-based organophosphorus insecticides such as chlorprazophos and pyrazophos; pyridine-based organophosphorus insecticides such as chlorpyrifos and chlorpyrifos-methyl; pyrimidine-based organophosphorus insecticides such as butathiophos, diazinon, etrymphos, lyrimphos, pyrimiphos-ethyl, pyrimiphos-methyl, primidophos, pyrimitate and tebupyrimphos; quinoxaline-based organophosphorus insecticides such as quinalphos and quinalphos-methyl; thiadiazole-based thiophosphorus insecticides such as atidation, lithidation, metidathione, and protidathione; triazole-based organophosphorus insecticides , such as isazophos and triazophos; organothiophosphorus insecticides based on phenyls , such as azotoate, bromophos, bromophos-ethyl, carbofenotion, chlorthiophos, cyanophos, cythioate, dicaptone, dichlofenthion, ethaphos, famfur, fenchlorvos, fenitrothion, fensulfothion, fenthion, fenthion-ethyl, heterophos, iodophenphos, mesulfenphos, parathion, parathion-methyl, phenkapton, fosnichlor, profenofos, prothiophos, sulprofos, temephos, trichlormetaphos-3 and tryfenofos; phosphonate-based insecticides , such as butonate and trichlorfon; thiophosphonate-based insecticides , such as mecarfon; insecticides based on phenylethylthiophosphonates , such as fonofos and trichloronate; insecticides based on phenyl-phenylthiophosphonates such as cyanofenphos, EPN and leptophos; phosphoramidate-based insecticides such as crufomat, fenamiphos, fostyethane, mephospholane, phospholane and pyrimetaphos; amidothiophosphate insecticides such as acephate, isocarbophos, isofenphos, isofenphos-methyl, methamidophos and propetamphos; phosphorus diamide insecticides such as dimefox, mazidox, mipafox and shradan; oxydiazine insecticides such as indoxacarb; oxadiazoline-based insecticides , such as methoxadiazone; phthalimide-based insecticides such as dialyphos, phosmet and tetramethrin; pyrazole-based insecticides such as tebufenpyrad, tolefenpyrad; phenylpyrazole-based insecticides such as acetoprol, ethiprole, fipronil, pyrafluprole, pyriprol and vaniliprole; pyrethroid ester insecticides such as acrinathrin, allethrin, bioallethrin, bartrin, bifenthrin, kappa bifenthrin, bioethanometrin, chloropralletrin, cyclothrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha -cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyfenotrin, deltamethrin, dimefluthrin, dimethrin, empentrin, fenfluthrin, fenpyrythrin, fenpropatrine, fenvalerate, esfenvalerate, flucitrinate, fluvalinate, tau-fluvalinate, furethrin, heptafluthrin, meperfluthrin , metofluthrin, epsilon-methofluthrin, momfluorothrin, epsilon-momfluorothrin, permethrin, biopermethrin, transpermethrin, phenothrin, pralletrin, profluthrin, pyresmethrin, resmethrin, bioresmethrin, cismetrin, tefluthrin, kappa-tefluthrin, teralletrin, tetramethrin, tetramethylfluthrin and transflumethrin; pyrethroid ether insecticides such as etofenprox, flufenprox, halfenprox, protrifenbut and silafluofen; pyrimidinamine-based insecticides such as flufenerim and pyrimidifen; pyrrole-based insecticides such as chlorfenapyr; tetramic acid insecticides , such as spiropidion and spirotetramat; tetronic acid insecticides such as spiromesifen; thiourea-based insecticides such as diafenthiuron; urea-based insecticides such as flucofuron and sulcofuron; unclassified nematicides such as fluazaindolizine and thioxazafen; and unclassified insecticides such as benzpyrimoxane, closantel, copper naphthenate, crotamiton, EXD, fenazaflor, fenoxacrim, fluhexafon, flupyrimine, hydramethylnon, isoprothiolane, malonobene, metaflumizone, nifluridide, oxazolsulphyl, plifenate, pyridaben, pyridalyl, pyrifluxanone, sulfoxaratenazonide, rafoxaratenazonide and triazamate; and any combinations thereof.

[0024] In addition, the compound I of the present invention can be combined with herbicides that are compatible with the compound I of the present invention in the environment selected for use and do not interfere with the activity of the compound I, to obtain pesticide mixtures and synergistic mixtures thereof. The fungicidal compound I of the present invention can be used in conjunction with one or more herbicides to control a wide range of undesirable plants. When used in conjunction with herbicides, Compound I as claimed herein may be formulated with the herbicide(s), tank-mixed with the herbicide(s), or applied sequentially with the herbicide(s). Exemplary herbicides include, without limitation:amide herbicides, such as allidochlor, beflubutamide, benzadox, benzipram, bromobutide, cafenstrole, CDEA, ciprazole, dimethenamid, dimethenamid-P, diphenamide, epronase, ethnipromide, fentrazamide, flupoxam, fomesafen, halosafen, isocarbamide, isoxaben, napropamide, naptalam, petoxamide, protoxamide, quinonamide, tebutam and thiafenacil;anilide herbicides, such as chloranocryl, cisanilide, clomeprop, cypromide, diflufenican, etobenzanide, fenasulam, flufenacet, flufenican, mefenacet, mefluidide, methamifop, monalide, naproanilide, pentanochlor, picolinafen and propanil;arylalanine herbicides, such as benzoylprop, flamprop and flamprop-M;chloroacetanilide herbicides,such as the acetochlor, alachlor, butachlor, butenachlor, delachlor, dietanil, dimethachlor, metazachlor, metolachlor, S-metolachlor, pretilachlor, propachlor, propisochlor, prinachlor, terbuchlor, tenichlor, and xylachlor;sulphonanilide herbicides,such as benzofluor, perfluidone, pyrimisulfan and profluazole;sulfonamide herbicides, such as asulam, carbasulam, fenasulam and oryzalin;thioamide herbicides, such as chlorothiamide;antibiotic herbicides, such as bilanaphos;herbicides based on benzoic acid, such as chloramben, dicamba, 2,3,6-TBA and tricamba; based herbicidespyrimidinyloxybenzoic acid,such as bispyribac and pyriminobac;herbicides based on pyrimidinylthiobenzoic acid, such as pyrithiobac;phthalic acid herbicides, such as chlorthal;herbicides based on picolinic acid, such as aminopyralid, clopyralid, florpyrauxifen, galauxifen and picloram;herbicides based on quinolinecarboxylic acid, such as quinclorac and quinmerac;arsenic herbicides, such as cacodylic acid, CMA, DSMA, hexaflurate, MAA, MAMA, MSMA, potassium arsenite and sodium arsenite;benzoylcyclohexanedione herbicides, such as fenquinotrion, lancotrione, mesotrione, sulcotrione, tefuryltrione and tembotrione;benzofuranylalkylsulfonate herbicides,such as benfuresate and etofumesate;benzothiazole herbicides, such as benzoline;carbamate herbicides, such as asulam, carboxazole chlorprocarb, dichlormate, fenasulam, carbutylate and terbucarb;carbanylate herbicides, such as barban, BCPC, carbasulam, carbetamide, CEPC, chlorbufam, chlorprofam, CPPC, desmedifam, fenizofam, phenmedifam, phenmedipham-ethyl, profam and swep;cyclohexenoxime herbicides,such as alloxydim, butroxydim, clethodim, cloproxidim, cyclooxydim, profoxydim, sethoxydim, tepraloxydim and tralkoxydim;cyclopropylisoxazole herbicides, such as isoxachlorotol and isoxaflutol;dicarboximide herbicides, such as cynidone-ethyl, flumezine, flumiclorac, flumioxazine and flumipropine;dinitroaniline herbicides, such as benfluranil, butralin, dinitramine, ethalfluralin, fluchloralin, isopropalin, metalpropalin, nitraline, oryzalin, pendimethalin, prodiamine, profluralin and trifluralin;dinitrophenol herbicides,such as dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etinophen and medinoterb;herbicides based on diphenyl ether,such as ethoxifen;herbicides based on nitrophenyl ether,such as acifluorfen, aclonifen, bifenox, chlomethoxifen, chlornitrophen, ethnipromide, fluorodifen, fluoroglycofen, fluoronitrofen, fomesafen, furyloxifen, halosafen, lactofen, nitrofen, nitrofluorfen and oxyfluorfen;dithiocarbamate herbicides,such as dazomet and metam;halogenated aliphatic herbicides, such as alorac, chloropon, dalapon, flupropanate, hexachloroacetone, iodomethane, methyl bromide, monochloroacetic acid, SMA and TCA;imidazolinone herbicides, such as imazametabenz, imazamox, imazapic, imazapyr, imazaquin and imazethapyr;inorganic herbicides,such as ammonium sulfamate, borax, calcium chlorate, copper sulfate, ferrous sulfate, potassium azide, potassium cyanate, sodium azide, sodium chlorate and sulfuric acid;nitrile herbicides, such as bromobonil, bromoxynil, chlorxynil, cyclopyranil, dichlobenil, iodobonil, ioxynil and pyraclonil;organophosphorus herbicides, such as amiprofos-methyl, anilophos, bensulide, bilanaphos, butamiphos, 2,4-DEP, DMPA, EBEP, fosamine, glufosinate, glufosinate-P, glyphosate and piperophos;phenoxy herbicides, such as bromfenoxime, clomeprop, 2,4-DEB, 2,4-DEP, diphenopentene, disul, erbon, ethnipromide, fenteracol and triphosme;oxadiazolinic herbicides, such as methazol, oxadiargyl, oxadiazon;oxazole herbicides, such as phenoxasulfone;phenoxyacetic herbicides,such as 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl and 2,4,5-T;phenoxy oil herbicides, such as 4-CPB, 2,4-DB, 3,4-DB, MCPB and 2,4,5-TB;phenoxypropionic herbicides, such as cloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop and mecoprop-P;aryloxyphenoxypropionic herbicides, such as chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fentiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapirifop, methamifop, propaquizafop, quizalofop, quizalofop-P and tripfop;phenylenediamine herbicides, such as dinitramine and prodiamine;pyrazole herbicides, such as pyroxasulfone;benzoylpyrazole herbicides, such as benzofenap, pyrasulfotol, pyrazolinate, pyrazoxifene, tolpyralate and topramesone;phenylpyrazole herbicides,such as fluazolate, nipiraclofen, pyoxaden and pyraflufen;pyridazine herbicides,such as credazine, cyclopyrimorate, pyridafol and pyridate;pyridazinone herbicides, such as bromopyrazone, chloridazone, dimidazone, flufenpyr, metflurazone, norflurazone, oxapirazone and pidanone;pyridine herbicides,such as aminopyralid, cliodinat, clopyralid, dithiopyr, florpyrauxifen, fluroxypyr, galauxifen, haloxydin, picloram, picolinafen, pyriclor, thiazopyr and triclopyr;pyrimidindiamine herbicides, such as iprimidam and thioclorim;quaternary ammonium herbicides, such as cyperquat, dietamquat, difenzoquat, diquat, morphamquat and paraquat;thiocarbamate herbicides,such as butylate, cycloate, diallate, EPTC, esprocarb, etiolate, isopolynate, methiobencarb, molinate, orbencarb, pebulate, prosulfocarb, puributicarb, sulfallate, thiobencarb, thiocarbazil, triallate and vernolate;thiocarbonate herbicides, such as dimexano, EXD and proxan;thiourea herbicides, such as methiuron;triazine herbicides, such as dipropetrin, indaziflam, triaziflam and trihydroxytriazine;chlortriazine herbicides, such as atrazine, chlorazine, cyanazine, ciprazine, eglinazine, ipazine, mesoprazine, procyazine, proglinazine, propazine, sebutylazine, simazine, terbutylazine and trietazine;methoxytriazine herbicides, such as atratone, methometon, promethone, secbumeton, simeton and terbumeton;methylthiotriazine herbicides, such as ametrin, aziprothrin, cyanathrin, desmetrin, dimethamethrin, metoprotrin, promethrin, symetrin and terbutrin;triazinon herbicides,such as ametridione, amibusin, hexazinon, isomethiosin, metamitron, metribuzin and trifludimoxazine;triazole herbicides,such as amitrol, cafenstrol, epronase and flupoxam;triazolone herbicides, such as amicarbazone, bencarbazone, carfentrazone, flucarbazone, ipfencarbazone, propoxycarbazone, sulfentrazone and thiencarbazone-methyl;triazolopyrimidine herbicides,such as cloransulam, diclosulam, florasulam, flumetsulam, methosulam, penoxulam and pyroxulam;uracil herbicides,such as benzfendison, bromacil, butafenacil, flupropacil, isocyl, lenacil, saflufenacil and terbacil;urea-based herbicidessuch as benzthiazuron, cumiluron, cycluron, dichloralurea, diflufenzopyr, isonoruron, isouron, metabenzthiazuron, monisouron and noruron;phenylurea herbicidessuch as anizuron, buturon, chlorbromuron, chlorethuron, chlorotoluron, chloroxuron, daimuron, difenoxuron, dimefuron, diuron, fenuron, fluometuron, fluothiuron, isoproturon, linuron, methiuron, methyldymron, methobenzuron, methobromuron, methoxuron, monolinuron, paralunuron , fenobenzuron, siduron, tetrafluron and thidiazuron;pyrimidinylsulfonylurea herbicidesSuch as amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flusetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, mesosulfuron, metazosulfuron, nicosulfuron, ortosulfamuron, oxasulfuron, primisulfuron, propirisulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron and trifloxysulfuron ;herbicides based on triazinylsulfonylureas, such as chlorsulfuron, cinosulfuron, etametsulfuron, iodosulfuron, iofensulfuron, metsulfuron, prosulfuron, thifensulfuron, triasulfuron, tribenuron, triflusulfuron and tritosulfuron;thiadiazolyl urea herbicidessuch as buthiuron, etidimuron, tebuthiuron, thiazafluron and thidiazuron; andunclassified herbicidessuch as acrolein, allyl alcohol, aminocyclopyrachlor, azaphenidine, bentazon, benzobicyclone, bicyclopyrone, butidazole, calcium cyanamide, cambendichlor, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, cinmethylin, clomazone, CPMF, cresol, cyanamide, cyclopyrimorate,orthodichlorobenzene, dimepiperate, endothal, fluoromidin, fluridone, flurochloridone, flurtamone, fluthiacet, indanophane, methylisothiocyanate, OCH, oxaziclomefon, pentachlorophenol, pentoxazone, phenylmercuracetate, prosulfalin, pyribenzoxime, pyrifthalide, quinoclamin, rodetanil, sulglycapine, thidiazimin, tridifan, trimethane, trimethane and tritak.

[0025] Compound I of the present invention may also contain or may be used together and/or sequentially with other active compounds. These additional compounds may be plant health promoters, such as organic compounds, inorganic fertilizers, or micronutrient donors, or other preparations that affect plant growth, such as inoculants.

[0026] In another embodiment, compound I may also contain or may be used together and/or sequentially with other biological organisms, such as, without limitation, organisms from the group consisting of Bacillus strains, for example, Bacillus subtilis var. amyloliquefaciens FZB24 (TAEGRP ^® ) and Bacillus amyloliquefaciens FZB42 (RHIZOVITAL ^® ), VotiVo™ Bacillus firmus , Clariva™ (Pasteuria nishizawae), Bacillus thuringiensis, Trichoderma spp., and/or mutants and metabolites of the respective strains that are active against insects, mites , nematodes and/or phytopathogens.

[0027] One embodiment of the present invention is a method for controlling or preventing fungal infestation. This method comprises applying to the soil, plant, roots, foliage, seed, or fungal site or location where infection is to be prevented (e.g., applying to crops or vine plants) a fungicidally effective amount of Compound I. Compound I is suitable for treatment various plants at fungicidal levels, while being characterized by low phytotoxicity. Compound I may be useful for pest control and/or pest control.

[0028] The compound of formula I has been found to have significant fungicidal effects, especially for agricultural use. The compound of formula I is particularly effective for use with crops and horticultural plants. Additional benefits may include, without limitation, improved plant health; improvement in plant yield (eg, increased biomass and/or increased content of valuable ingredients); improved plant vigor ( eg improved plant growth and/or greener leaves); improving the quality of the plant ( for example , improved content or composition of certain ingredients); and improving the resistance of the plant to abiotic and/or biotic stress.

[0029] In particular, the composition is effective in controlling a number of undesirable fungi that infect useful vegetable crops. The composition can be used against a number of ascomycetes and basidiomycetes , including, for example, the following typical fungal species.

[0030] On cucurbits: powdery mildew ( Erysiphe cichoracearum , Sphaerotheca fuliginea ), ring spot ( Mycosphaerella brassicicola ), blackleg ( Plenodomus lingam ), anthracnose ( Colletotrichum higginsianum , Colletotrichum obiculare , Colletotrichum spp. , Glomerella lagenarium ), black rot ( Mycosphaerella melonis , Didymella bryoniae , Stagonosporopsis cucurbitacearum ); leaf spot and leaf damage caused by members of the genus Alternaria ( Alternaria cucumerina , Alternaria alternata f. sp. cucurbitae , Alternaria spp. ), leaf spot caused by members of the genus Cercospora ( Cercospora citrullina , Cercospora spp. ), fusarium wilt ( Fusarium oxysporum ), Rhizoctonia rot ( Rhizoctonia solani ), Corynespora/target spot disease ( Corynespora cassiicola ), Cladosporiosis ( Cladosporium cucumerinum ), Verticillium wilt ( Verticillium dahliae, Verticillium albo-atrum ), Black root rot ( Thielaviopsis basicola ), Blue rot ( Penicillium spp.), sclerocial rot ( Macrophomina phaseolina ) and rhizoctonia (fruit) ( Myrothecium roridum ).

[0031] On Tomato: Powdery mildew ( Leveillula taurica ), Septoria leaf spot ( Septoria lycopersici ), white rot ( Sclerotinia sclerotiorum, Sclerotinia minor ), target spot ( Corynespora cassiicola ), southern sclerotium rot ( Sclerotium rolfsii ) , gray mold ( Botrytis cinerea ), gray leaf spot ( Stemphylium spp.), fusarium wilt, Fusarium collar and root rot ( Fusarium oxysporum ), anthracnose ( Colletotrichum coccodes, Colletotrichum dematium, Colletotrichum gloeosporioides, Glomerella cingulate ), stem cancer and black rot caused by members of the genus Alternaria ( Alternaria alternata ), black root rot ( Chalara elegans ), leaf mold caused by members of the genus Cercospora ( Cercospora fuligena ), sclerocial rot ( Macrophomina phaseolina ), cork root rot ( Pyrenochaeta lycopersici ), stem rot caused by members of the genus Didymella ( Didymella lycopersici ), dry spot ( Alternaria solani ), leaf mold ( Passalora fulva, Mycovellosiella fulva ), phomosis rot ( Phoma destructiva ) and acid rot ( Geotrichum candidum ).

[0032] On leafy vegetables: leaf spot caused by members of the genus Cercospora ( Cercospora longissimi , Cercospora spp. ), gray mold/rot caused by members of the genus Botrytis ( Botrytis cinerea ), leaf spot and leaf damage caused by members of the genus Alternaria ( Alternaria sonchi , Alternaria spp. ), powdery mildew ( Erysiphe cichoracearum , Golovinomyces cichoracearum , Uncinula spp. ), rust ( Puccinia dioicae ), leaf spot caused by members of the genus Septoria ( Septoria lactucae, Septoria spp. ), southern sclerotial rot ( Sclerotium rolfsii ) , button rot ( Phoma exigua ), white stalk ( Rhizoctonia solani ), sclerotial rot ( Sclerotinia minor , Sclerotinia sclerotiorum ), and leaf spot caused by members of the genus Stemphylium ( Stemphylium botryosum ).

[0033] On potatoes: anthracnose or black dot (Colletotrichum coccodes), brown spotting and black pitting (Alternaria alternata), leaf cercosporiosis (Cercospora concors), sclerocial rot (Macrophomina phaseolina), brown rust (Puccinia pittieriana), deforming rust (Aecidium cantensis), dry spotting (Alternaria solani), dry fusarium rot and fusarium wilt (Fusarium spp.), gangrene (Phoma exiguaf. sp.foveata), gray mold (Botrytis cinerea), black spot or fomosa leaf spot (Stagonosporopsis andigena,Phoma andigena var. andinai), powdery mildew (Erysiphe cichoracearum), cancer and black scab caused by members of the genus Rhizoctonia (Rhizoctonia solani), black rot caused by representatives of the genus Rosellinia (Rosellinia spp.), leaf spot caused by representatives of the genus Septoria (Septoria lycopersici var. malagutil), silver scab (Helminthosporium solani), tuberous scab (Polyscytalum pustulans), stem rot. (Sclerotium rolfsii), smut caused by representatives of the genus Thecaphora (Thecaphora solani), a rot caused by members of the genus Ulocladium (Ulocladium atrum), verticillium wilt (Verticillium albo-atrum) and white rot (Sclerotinia sclerotiorum).

[0034] On pepper plants: southern sclerotial rot ( Sclerotium rolfsii ), powdery mildew ( Leveillula taurica ), anthracnose ( Colletotrichum capsici , Colletorichum acutatum , Colletorichum spp. ), leaf spot caused by members of the genus Cercospora (ring spot) ( Cercospora capsici , Cercospora spp. ), sclerocial rot ( Macrophomina phaseolina ), rhizoctiniosis and root rot ( Rhizoctonia solani ), stem rot of the genus Fusarium ( Fusarium solani ), Fusarium wilt ( Fusarium oxysporum f. sp. capsici ), gray leaf spot ( Stemphylium spp. ), gray mold ( Botrytis cinerea ), verticillium wilt ( Verticillium albo-atrum ) and white mold ( Sclerotinia sclerotiorum ).

[0035] On cabbage crops: leaf spot and leaf damage caused by members of the genus Alternaria (Alternaria brassicicola, Alternaria spp.), anthracnose (Colletotrichum spp.), black leg (Leptosphaeria maculans,Phoma lingam), leaf spot caused by members of the genus Cercospora (Cercopsora spp.), jaundice and other diseases caused by representatives of the genus Fusarium(Fusarium spp.), gray mold/blotch caused by members of the genus Botrytis (Botrytis cinerea), powdery mildew (Erysiphe polygoni), rot and spot caused by members of the genus Rhizoctonia (Rhizoctonia solani), ring spotting (Mycosphaerella brassicicola), sclerocial rot (Sclerotinia spp.), white leaf spot (Pseudocercosporella capsellae).

[0036] Compound I has been found to have significant fungicidal effects against phytopathogenic fungi of agriculturally beneficial vegetable crops. These diseases include Alternaria brassicicola , which causes black spot on cabbage leaves; Alternaria solani , which causes dry spotting of tomatoes; Sclerotinia sclerotiorum, which causes sclerocial rot in lettuce; Colletotrichum capsici , which causes anthracnose in hot peppers; Erysiphe cichoracearum , which causes cucumber powdery mildew; Mycovellosiella fulva , which causes tomato leaf mold; Stagonosporopsis cucurbitacearum , which causes mycospherella black rot in watermelon; and Botrytis cinerea , which causes gray mold of the horticultural bean, in particular for agricultural use. Compound I is particularly effective for use with crops and horticultural plants.

[0037] Compound I has a wide range of efficacy as a fungicide. The exact amount of active material to be used depends not only on the particular active material being used, but also on the particular action required, the fungus species being controlled and its growth stage, and the part of the plant or other product being contacts the connection. Thus, Compound I and formulations containing it may not be equally effective at comparable concentrations or against the same species of fungus.

[0038] Compound I is effective when applied to plants in an amount that suppresses disease and is acceptable to the plant. The term "disease-inhibiting amount and acceptable to the plant" refers to an amount of a compound that eliminates or inhibits a plant disease, control of which is desirable but is not highly toxic to the plant. This amount will typically be from about 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm being preferred. The exact concentration of the compound required will vary depending on the fungal disease being controlled, the type of formulation used, method of application, specific plant species, climatic conditions, and so forth. A suitable application rate is typically in the range of about 0.10 to about 4 pounds/acre (about 0.01 to 0.45 grams per square meter, g/m ² ).

[0039] Any range or desired value specified herein can be increased or changed without losing the intended effects, which is obvious to a person skilled in the art to understand the ideas of this document.

Examples

Field evaluation of Alternaria brassicicola (ALTEBI) on cabbage

[0040] A fungicidal treatment containing Compound I applied as a 5% EC formulation and tank-mixed with adjuvant (Trycol, 50% w/w at 0.2% v/v) was sprayed onto the plants head cabbage (BRSOL) three times, with the first application being at the cabbage plant development stage 10-12 LF. The following applications were made at 7 day intervals, with all applications being sprayed at rates of 50, 100 and 150 grams of active ingredient per hectare (g a.i./ha). Experimental test plots were inoculated with black leaf pathogen 2 days after the first application. The application was part of an experimental trial designed in a randomized full block design with four repetitions and an experimental plot of approximately 2×1 m, while compound I was applied at a water volume of 800 l/ha.

[0041] Disease severity was assessed as a percentage of the area affected by lower cabbage foliage (6 plants per plot, randomly). Visual assessment of infection damage was performed three times during the test 7 days after each application. The area under the disease course curve (AUDPC) was calculated for each test site using the severity datasets. Relative AUDPC (% effectiveness of control based on AUDPC) was calculated as a percentage of the untreated control. The results are shown in table 1.

Field evaluation of Sclerotinia sclerotiorum (SCLESC) on lettuce

[0042] A fungicide containing 5% EC formulation based on Compound I plus an excipient (Trycol, 50% w/w at 0.2% v/v) was sprayed on head lettuce plants (LACSC) twice : The first application was carried out at the heading stage 36 days after planting and the second application was carried out 7 days later. Compound I formulations were applied at rates of 50, 100 and 150 grams active ingredient per hectare (g a.i./ha). Experimental test plots were inoculated with sclerotial rot pathogen 2 days after the first application. The treatment was part of an experimental trial designed in a randomized full block design with four repetitions and a test plot of approximately 2×1 m, with Compound I formulations applied at a water volume of 800 l/ha.

[0043] The percentage infection rate for the disease was calculated using the equation (stem damage length values)/(stem length sum) x 100% per plant (6 plants per plot randomly). Sclerotial rot infection was assessed four times: 7 days after application of A (DAAA), plus 7, 14 and 21 DAAB. The area under the curve describing the course of the disease (AUDPC) was calculated for each experimental site using the sets of recorded data on visual assessment of infection. Relative AUDPC (% effectiveness of control based on AUDPC) was calculated as a percentage of the untreated control. The results are shown in table 1.

Field evaluation of Colletotrichum capsici (COLLCA) on hot pepper plants

[0044] Compound I was evaluated for COLLCA in hot pepper plants, both in protection and treatment formats, in two separate field trials. During a 2-day protection test, a fungicidal treatment containing 5% EC formulation based on Compound I plus an excipient (Trycol, 50% w/w at 0.2% v/v) was sprayed onto the plants hot pepper (CPSAN) three times: the first application was carried out during flowering and fruiting 43 days after planting, and subsequent applications at 7-day intervals. Compound I formulations were applied at rates of 50, 100 and 150 grams active ingredient per hectare (g a.i./ha). Experimental test plots were inoculated with an anthracnose pathogen 2 days after the first application. The treatment was part of an experimental trial designed in a randomized full block design with four repetitions and an experimental plot of approximately 2×1 m, while the compositions based on compound I were applied at a water volume of 1000 l/ha.

[0045] Disease severity was assessed as the percentage of fruit area affected by disease per plant (6 plants per plot, random). Anthracnose infection was assessed four times: 7 days after application of A (DAAA), 7 DAAB plus 7 and 14 DAAC. The area under the curve describing the course of the disease (AUDPC) was calculated for each experimental site using the sets of recorded data on visual assessment of infection. Relative AUDPC (% effectiveness of control based on AUDPC) was calculated as a percentage of the untreated control. The results are shown in table 1.

[0046] During a 4-day treatment-providing test, a fungicidal treatment containing 5% Compound I EC formulation plus excipient (Trycol, 50% w/w at 0.2% v/v) sprayed on hot pepper plants (CPSAN) twice: the first application was carried out during flowering and fruiting 59 days after planting, while the second application - after 7 days. Compound I formulations were applied at rates of 50, 100, 150 and 200 grams active ingredient per hectare (g a.i./ha). Experimental test plots were inoculated with an anthracnose pathogen 4 days before the first application (with provision of treatment). The treatment was part of an experimental trial designed in a randomized full block design with four repetitions and an experimental plot of approximately 2×1 m, while the compositions based on compound I were applied at a water volume of 1200 l/ha.

[0047] Disease severity was assessed as the percentage of fruit area affected by disease per plant (6 plants per plot, random). Anthracnose infection was assessed four times: 7 days after application of A (DAAA), plus 7, 14 and 21 DAAB. The area under the curve describing the course of the disease (AUDPC) was calculated for each experimental site using the sets of recorded data on visual assessment of infection. Relative AUDPC (% effectiveness of control based on AUDPC) was calculated as a percentage of the untreated control. The results are shown in table 1.

Field evaluation of Erysiphe cichoracearum (ERYSCI) on cucumber

[0048] Compound I was evaluated for ERYSCI in cucumber plants, in both protection and treatment formats, in two separate field trials. During a 2 day protection test (2DP), a fungicidal treatment containing 5% EC formulation based on Compound I plus an excipient (Trycol, 50% w/w at 0.2% v/v) was sprayed onto cucumber plants (CUMSA) twice: the first application was carried out at the fruiting stage 41 days after planting, and the subsequent application after 7 days. Compound I formulations were applied at rates of 50, 100 and 150 grams active ingredient per hectare (g a.i./ha). Experimental plots were inoculated with powdery mildew pathogen 2 days after the first application. The treatment was part of a pilot trial designed in a randomized full block design with four repetitions and a trial plot of approximately 2×1 m, with compounds based on compound I applied at a water volume of 1200 l/ha based on the size of the seedlings.

[0049] Disease severity was assessed as the percentage of cucumber foliage area affected by disease per plant (6 plants per plot, random). Powdery mildew infection of cucumbers was evaluated three times: 7 days after application of A (DAAA), and 7 and 14 DAAB. The area under the curve describing the course of the disease (AUDPC) was calculated for each experimental site using the sets of recorded data on visual assessment of infection. Relative AUDPC (% effectiveness of control based on AUDPC) was calculated as a percentage of the untreated control. The results are shown in table 1.

[0050] In a treatment trial, a fungicidal treatment containing 5% Compound I EC formulation plus an excipient (Trycol, 50% w/w at 0.2% v/v) was sprayed onto plants cucumber (CUMSA) twice: the first application was carried out at the fruiting stage 29 days after planting, while the second application was carried out after 7 days. Compound I formulations were applied at rates of 50, 100 and 150 grams active ingredient per hectare (g a.i./ha). Experimental test plots were inoculated with powdery mildew pathogen 2 days before the first application (with provision of treatment). The treatment was part of a pilot trial designed in a randomized full block design with four repetitions and a trial plot of approximately 2×1 m, with compounds based on compound I applied at a water volume of 1200 l/ha based on the size of the seedlings.

[0051] Disease severity was assessed as the percentage of cucumber foliage area affected by disease per plant (6 plants per plot, random). Powdery mildew disease severity was assessed four times: 7 days after application of A (DAAA) plus 7, 14 and 21 DAAB. The area under the curve describing the course of the disease (AUDPC) was calculated for each experimental site using the sets of recorded data on visual assessment of infection. Relative AUDPC (% effectiveness of control based on AUDPC) was calculated as a percentage of the untreated control. The results are shown in table 1.

Field evaluation of Alternaria solani (ALTESO) on tomato

[0052] Compound I was evaluated for ALTESO in tomato in two separate field trials. In the first test, a fungicidal treatment containing Compound I, applied both as a 5% EC formulation and as a 10% SC formulation, was mixed in an adjuvant tank (Agnique BP420, 50% w/w at 0 3% v/v) were sprayed onto tomato plants (LYPES) at a height of about 60-70 cm at rates of 100 and 200 grams of active ingredient per hectare (g a.i./ha). The test was based on five foliar applications at 7 day intervals, inoculated with dry spot pathogen 2 days after the first application. The treatment was part of an experimental trial designed in a randomized full block design with four repetitions and an experimental plot of approximately 1.5 x 4 m. Compound I was applied at a water volume of 1000 l/ha using an AZO backpack sprayer using compressed air.

[0053] Disease severity was recorded as the percentage of area affected by the disease on a random sample of 20 leaves and 20 fruits per test plot. Percent control efficacy was assessed using 6 evaluations performed between 0-35 days after the first application, DAA1. The area under the disease course curve (AUDPC) was calculated for each test site using the severity datasets. Relative AUDPC (% effectiveness of control based on AUDPC) was calculated as a percentage of the untreated control. The results are shown in table 2.

[0054] In a repeat test, a fungicidal treatment containing Compound I, used both as a 5% EC formulation and as a 10% SC formulation, and mixed in an adjuvant tank (Agnique BP420, 50% wt/ wt at 0.3% v/v) were sprayed on tomato plants (LYPES, cv. Taylor) about 21 days after planting. Compound I formulations were applied at rates of 100 and 200 grams of active ingredient per hectare (g a.i./ha). The test was based on six foliar applications at 10 day intervals under natural pressure exerted by the tomato dry spot pathogen. The treatment was part of an experimental trial designed in a randomized full block design with four repetitions and a trial plot of approximately 2×4 m. Compound I formulations were applied at a water volume of 800 L/ha using a knapsack sprayer for trial plots (BKPCKENG, Solo 443; HCSOLID - Albutz ATR80 Orange Nozzle), and at a pressure of 300 kPa. The disease severity (percent control efficiency) was recorded as the percentage infection of the leaves obtained by visual assessment in the test plot and was evaluated 10 days after the last application. The results are shown in table 2.

Field evaluation of Mycovellosiella fulva (FULVFU) on tomato

[0055] A 10% SC formulation based on Compound I was tank mixed with four different excipients: Agnique BP420 (50% w/w at 0.3% v/v); Trycol (50% w/w at 0.1% v/v); Ethomeen T18H (50% w/w at 0.2% v/v); and Phase II (50% w/w at 0.2% v/v). A fungicidal treatment containing formulations based on compound I, either alone or with excipients, was sprayed on tomato plants four times: the first application was carried out approximately 3 months after planting, and the subsequent three applications at 7-10 day intervals. Compound I formulations were applied at rates of 50, 100, 150 and 200 grams active ingredient per hectare (g a.i./ha). Experimental test plots were inoculated with leaf mold pathogen 7 days prior to first application (with treatment provided). The treatment was part of an experimental trial designed in a randomized full block design with four repetitions and an experimental plot of approximately 2.5 x 1.4 m. Formulations based on Compound I were applied with a water volume of 675 l/ha.

[0056] Disease severity was recorded as the percentage of diseased foliage obtained by visual assessment (6 plants per plot, random). Tomato leaf mold infection was assessed five times: 7 days after the first application (7 DAAA), 7 DAAB, 5 DAAC, followed by 7 and 12 DAAD. The area under the disease course curve (AUDPC) was calculated for each test site using the severity datasets. Relative AUDPC (% effectiveness of control based on AUDPC) was calculated as a percentage of the untreated control. The results are shown in table 3.

Field evaluation of Stagonosporopsis cucurbitacearum (DIDYBR) on watermelon

[0057] A 10% SC formulation based on Compound I was tank mixed with four different excipients: Agnique BP420 (50% w/w at 0.3% v/v); Trycol (50% w/w at 0.1% v/v); Ethomeen T18H (50% w/w at 0.2% v/v); and Phase II (50% w/w at 0.2% v/v). A fungicidal treatment containing formulations based on Compound I, either alone or with excipients, was sprayed on watermelon plants four times: the first application was carried out approximately 2 months after planting, and the subsequent three applications at 7-10 day intervals. Compound I formulations were applied at rates of 50, 100, 150 and 200 grams active ingredient per hectare (g a.i./ha). Experimental test plots were inoculated with a pathogen causing mycospherella black rot 2 days after the first application. The treatment was part of an experimental trial designed in a randomized full block design with four repetitions and an experimental plot of approximately 2.5 x 1.4 m. Formulations based on Compound I were applied with a water volume of 675 l/ha.

[0058] Disease severity was recorded as stem damage length and as percentage of foliage area affected by disease (3 plants per plot, random). Watermelon black rot infection was assessed twice: the first time 6 days after the first application (6 DAAA), followed by 19 DAAD. The area under the disease course curve (AUDPC) was calculated for each test site using the severity datasets. Relative AUDPC (% effectiveness of control based on AUDPC) was calculated as a percentage of the untreated control. The results are shown in table 4.

Greenhouse assessment of Botrytis cinerea (BOTRCI) on a garden bean

[0059] Technical grade materials were dissolved in acetone, then mixed with nine volumes of water containing 100 ppm Triton X-100. Fungicide formulations were applied to plant seedlings using an automatic spray booth to carry out the outflow. All sprayed plants were allowed to dry before further treatment. The test plants were inoculated with Botrytis cinerea 1 day after application. When the untreated plants showed full symptoms of the disease, the percentage of plant area affected by the disease was evaluated on a scale from 0 to 100 percent of the severity of the disease. The percentage control efficiency of the disease was calculated using the ratio of disease severity of treated plants to untreated plants. The results are shown in table 5.

[0060] For each Table 1-5, the AUDPC-based control effectiveness rating scale is as follows:

Control efficiency, % Grade 76-100 A 51-75 B 26-50 C 1-25 D Haven't experienced E

Table 1. Percentage control efficacy provided by Compound ^Ia against fungal diseases of vegetables, based on the area under the curve describing the course of the disease (AUDPC) in the protective and curative tests.

ALTEBI ^b SCLESC ^c COLLCA ^d ERYSCI ^e Norm
(g a.i./ha) ^f 2DP ^g 2DP 2DP 4 DC ^h 2DP 2 DC fifty C B A C A A 100 B A A B A B 150 B A A B A C 200 E E E B E E

^a Compound I was used as a 5% EC formulation with Trycol excipient (50% w/w at 0.2% v/v)

^b Black leaf spot of cabbage - Alternaria brassicicola

^c Lettuce sclerotial rot - Sclerotinia sclerotiorum

^d Hot pepper anthracnose - Colletotrichum capsici

^e Powdery mildew of cucumber - Erysiphe cichoracearum

^f Grams of active ingredient per hectare

^g 2-day protection

^h 4 days with treatment

Table 2 Efficacy of Compound I ^a against dry spot (ALTESO, Alternaria solani ) on tomato leaves and fruit in EC and SC formulations.

leaves ^b
Trial 1 fruits ^c
Trial 1 leaves ^b
Trial 2 Norm
(g a.i./ha) ^d 5%EC 10% SC 5%EC 10% SC 5%EC 10% SC 100 A A A A A A 200 A A A A A A

^a Compound I was used with the excipient Agnique BP420 (50% w/w at 0.3% v/v).

^b Percentage disease control efficiency in tomato leaves based on area under the disease course curve (AUDPC)

^c Percentage disease control efficiency in tomato fruits, based on the area under the curve describing the course of the disease (AUDPC)

^d Grams of active ingredient per hectare

Table 3 Efficacy ^a of Compound I against tomato leaf mold (FULVFU, Mycovellosiella fulva ) at 10% SC formulation with or without auxiliary agent.

Excipient Norm
(g a.i./ha) ^{b Ic} II ^d III ^e IV ^{f Vg} fifty C A NT NT NT 100 C A A B A 150 NT A NT NT NT 200 NT A NT NT NT

^a Percentage of control effectiveness based on the area under the curve describing the course of the disease (AUDPC)

^b Grams of active ingredient per hectare

^c I - Without excipient

^d II - Agnique BP420 (50% w/w at 0.3% v/v)

^e III - Trycol (50% w/w at 0.1% v/v)

^f IV - Ethomeen T18H (50% w/w at 0.2% v/v)

^g V - Phase II (50% w/w at 0.2% v/v)

Table 4 Efficacy ^a of compound I against mycospherella black rot of watermelon (DIDYBR, Stagonosporopsis cucurbitacearum ) in 10% SC formulation with or without excipient

Excipient Norm
(g a.i./ha) ^b I ^c II ^d III ^e IV ^{f Vg} fifty NT A NT NT NT 100 B A B B B 150 NT A NT NT NT 200 NT A NT NT NT

^a Percentage of control effectiveness based on the area under the curve describing the course of the disease (AUDPC)

^b Grams of active ingredient per hectare

^c I - Without excipient

^d II - Agnique BP420 (50% w/w at 0.3% v/v)

^e III - Trycol (50% w/w at 0.1% v/v)

^f IV - Ethomeen T18H (50% w/w at 0.2% v/v)

^g V - Phase II (50% w/w at 0.2% v/v)

Table 5 Efficacy of Compound I against Orchard Bean Gray Rot (BOTRCI, Botrytis cinerea ).

Norm
(ppm) ^a Control efficiency, % ^b 400 A 100 A 25 A 6.25 B

^a Parts per million

^b Percentage control efficiency, calculated by the ratio of disease severity of treated plants to untreated plants

Field evaluation of Corynespora cassiicola (CORYCA) on tomato

[0061] A fungicidal treatment containing Compound I applied as an SC formulation (MSO based) and tank-mixed with adjuvant (Agnique BP-420, 50% w/w at 0.2% v/v or Adsee C80W 80%), sprayed on tomato plants (LYPES, cultivar Charger) at the growth stage of BBCH64 (4th open flower) at rates of 50, 75, 100 and 150 grams of active ingredient per hectare (g a.i./ha). The experimental test plots were inoculated with the target spotting pathogen one day after the initial application. The treatment was part of an experimental trial designed in a randomized full block design (RCB) with four repetitions and an experimental plot of approximately 6×25 Nm (ft). Compound I was applied at a water volume of 100 gallons per acre (gallons/acre) using a tractor sprayer (SCDISC D1 nozzles) and at a pressure of 200 psi. inch.

[0062] Disease severity (percentage of diseased foliage (leaf) obtained by visual assessment in the entire experimental plot) was assessed four times during the test (1-20 days after application, DAA). The area under the curve describing the course of the disease (AUDPC) was calculated for each experimental site using the severity data sets. Relative AUDPC (control efficiency in % based on AUDPC) was calculated as a percentage of the untreated control. The results are shown in table 6.

Field evaluation of Colletotrichum coccodes (COLLCA) on tomato

[0063] A fungicidal treatment containing Compound I applied as an SC formulation (MSO based) and tank-mixed with adjuvant (Agnique BP-420, 50% w/w at 0.2% v/v or Adsee C80W 80%), sprayed on tomato plants (LYPES, cultivar type Roma VS Saladette) at growth stage 12 of vegetative growth at rates of 50, 75, 100 and 150 grams of active ingredient per hectare (g a.i./ha) Experimental test plots were subjected to natural infection with an anthracnose pathogen and supplemented with a second inoculation approximately one day after the 1st applications. The treatment was part of an experimental trial designed in a randomized full block design (RCB) with four repetitions and an experimental area of approximately 6.67×30 feet. Compound I was applied at a water volume of 40 gal/acre using a knapsack sprayer (carbon dioxide (CO₂), 8004VS FF nozzles) and 38 psi. inch.

[0064] The severity of leaf damage in percent was assessed three times during the test (0-23 days after application 1). The area under the curve describing the course of the disease (AUDPC) was calculated for each experimental plot using the recorded data on the severity of leaf damage. Relative AUDPC (control efficiency in % based on AUDPC) was calculated as a percentage of the untreated control. The results are shown in table 7.

Table 6 Comparison of formulations based on Compound I with MSO or tank-blended with Agnique BP-420 based on the calculated percentage control effectiveness against tomato target spot (CORYCA, Corynespora cassiicola )

Compound I ^a Excipient ^{a or b} Percent CORYCA Control Efficiency (AUDPC) fifty MSO, ^100a 55.2 75 MSO, ^150a 56.1 100 MSO, ^200a 71.6 150 MSO, ^300a 84.0 fifty Agnique ^BP420 , 200b 53.1 75 Agnique BP420, ^300b 56.9 100 Agnique BP420, ^400b 74.1 150 Agnique BP420, ^600b 83.9 100 Adsee C80W 80%, 250 ^a 61.4

^a Norm in g/ha

^b Norm in ml/ha

Table 7 Comparison of formulations based on Compound I with MSO or tank-mixed with Agnique BP-420 based on the calculated percentage control efficiency against tomato anthracnose (COLLCA, Colletotrichum coccodes )

Compound I ^a Excipient ^{a or b} Percent COLLCA Control Efficiency (AUDPC) fifty MSO, ^100a 46.0 75 MSO, ^150a 75.5 100 MSO, ^200a 92.6 150 MSO, ^300a 95.3 fifty Agnique ^BP420 , 200b 67 75 Agnique BP420, ^2300b 91.1 100 Agnique BP420, ^400b 91.0 150 Agnique BP420, ^600b 95.7 100 Adsee C80W 80%, 250 ^a 57.3

^a Norm in g / ha.

^b Norm in ml/ha.

Claims (4)

1. A method for controlling fungal diseases in vegetable crops selected from cucurbits, tomatoes, leafy vegetables, potatoes, pepper plants and horticultural beans that are at risk of disease, comprising the steps of bringing into contact at least a part of the plant and/or an area adjacent to plant, with compound I or with a composition containing compound I:

wherein said compound is effective against a plant pathogen, and wherein the fungal pathogen is selected from the group consisting of cabbage black spot (Alternaria brassicicola), lettuce sclerotia rot (Sclerotinia sclerotiorum), hot pepper anthracnose (Colletotrichum capsici), tomato leaf mold ( Mycovellosiella fulva), mycospherella black rot of watermelon (Stagonosporopsis cucurbitacearum), gray bean rot (Botrytis cinerea), tomato target spot (Corynespora cassiicola) and tomato anthracnose (Colletotrichum coccodes). 2. The method of claim 1, wherein the composition further comprises at least one additional agriculturally active ingredient selected from the group consisting of insecticide, herbicide and fungicide.