BR112019023042B1 - USE OF AN ACYCLIC PICOLINAMIDE COMPOUND AS A FUNGICIDE FOR CONTROL OF PHYTOPATHOGENIC FUNGI ON VEGETABLES - Google Patents

Abstract

The present description refers to the field of agrochemicals, including compound i and its uses to control fungal diseases in vegetables useful in agriculture.

Description

CROSS REFERENCE TO RELATED ORDERS

[0001] This application claims the benefit of US Provisional Patent Application 62/500,172, filed on May 2, 2017, which is expressly incorporated herein by reference.

FIELD

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

BACKGROUND AND SUMMARY

[0003] Fungicides are compounds of natural or synthetic origin that act to protect and cure plants against damage caused by agriculturally relevant fungi. Generally, no single fungicide is useful in all situations. Consequently, research is underway to produce fungicides that can perform better, are easier to use, and are less expensive.

[0004] The present description refers 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 may offer protection against ascomycetes, basidiomycetes and deuteromycetes.

[0005] An embodiment of the present disclosure includes a method for controlling a pathogen-induced disease in a plant that is at risk of becoming ill from a pathogen that comprises placing the plant or an area adjacent to the plant in contact with a composition that includes Compound I.

[0006] Another embodiment of the present description is a use of Compound I for protecting a plant against attack by a phytopathogenic organism or for treating a plant infested by a phytopathogenic organism, comprising the application of Compound I, or a composition that includes Compound I to the soil, a plant, a part of the plant, the foliage and/or the roots.

[0007] Additionally, another embodiment of the present description is a composition useful for protecting a plant against attack by a phytopathogenic organism and/or for treating a plant infested by a phytopathogenic organism comprising Compound I and a phytologically acceptable carrier material.

DETAILED DESCRIPTION

[0008] An exemplary embodiment of the present description includes mixtures for controlling the growth of fungi, the mixture including Compound I:

[0009] Compound I of the present description can be applied by any variety of known techniques, either as Compound I or as formulations comprising Compound I. For example, Compound I can be applied to roots, stems, seeds, flowers, or foliage of plants to control various fungi, without damaging the commercial value of the plants. Compound I can also be applied as a foliar spray, soil spray, soil incorporation, chemigation, soil drench, soil injection or seed treatment. The material can be applied in the form of any generally used type of formulation, for example, as solutions, powders, soluble powders, dispersible concentrates or emulsifiable concentrates.

[0010] Preferably, Compound I of the present description is applied in the form of a formulation, including Compound I with a phytologically acceptable carrier. Concentrated formulations can be dispersed in water or other liquids for application or formulations can be powder-like or granular, which can be applied without further treatment. The formulations can be prepared according to procedures that are conventional in the art of agricultural chemistry.

[0011] The present description contemplates all vehicles by which Compound I can be formulated for administration and use as a fungicide. Typically, formulations are applied as aqueous suspensions or emulsions. These suspensions or emulsions can be produced from water-soluble, water-suspended or emulsifiable formulations that are solid, generally known as soluble powders; or liquids generally known as emulsifiable concentrates, aqueous suspensions or suspension concentrates. As will be readily appreciated, it is possible to use any material to which Compound I can be added, as long as it results in the desired utility without significant interference with the activity of Compound I as an antifungal agent.

[0012] Soluble powders, which can be compacted to form water-dispersible granules, comprise an integral mixture including Compound I, an inert carrier and surfactants. The concentration of Compound I in the soluble powder can be from about 10 percent by weight to about 90 percent by weight based on the total weight of the soluble powder, more preferably, about 25 percent by weight to about 75 percent by weight. Weight. In preparing soluble powder formulations, Compound I may be combined with any finely divided solid, such as prophyllite, talc, chalk, gypsum, Fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clay, diatomaceous earth , purified silicates or similar. In these operations, the finely divided carrier and surfactants are typically mixed with Compound I and ground.

[0013] Emulsifiable concentrates of Compound I may comprise a convenient concentration, such as from about 10 weight percent to about 50 weight percent of Compound I, in a suitable liquid, based on the total weight of the concentrate. Compound I can be dissolved in an inert vehicle that is a water-miscible solvent or a mixture of water-immiscible organic solvents and emulsifiers. Concentrates can be diluted with water and oil to form spray mixtures in the form of oil-in-water emulsions. Useful organic solvents include aromatics, especially the high boiling naphthalene and olefinic portions of petroleum, such as heavy aromatic naphtha. Other organic solvents can 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 used advantageously herein can be readily 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 aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as alkyl phenols. ethoxylated and carboxylic esters solubilized with polyol or polyoxyalkylene. Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include the oil-soluble salts (e.g., calcium) of alkylaryl sulfonic acids, oil-soluble salts or sulfated polyglycol ethers, and appropriate salts of phosphate polyglycol ether.

[0015] Representative organic liquids that can be used in the preparation of 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; dialkyl amides of various fatty acids, particularly, dimethyl amides of fatty glycols and glycol derivatives such as n-butyl ether, ethyl ether or methyl ether of diethylene glycol and methyl ether of triethylene glycol and the like. Mixtures of two or more organic liquids can also be used in preparing the emulsifiable concentrate. Organic liquids include xylene and propyl benzene fractions with xylene being most preferred in some cases. Dispersing surfactants are typically employed in liquid formulations and in an amount of 0.1 to 20 weight percent based on the combined weight of the dispersing agent and Compound I. The formulations may also contain other compatible additives, e.g., water regulators. plant growth and other biologically active compounds used in agriculture.

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

[0017] Compound I can also be applied as a granular formulation which is particularly useful for soil applications. Granular formulations generally contain from about 0.5 to about 10 weight percent based on the total weight of the granular formulation of Compound I dispersed in an inert vehicle consisting entirely or largely of coarsely divided inert material such as attapulgite, bentonite, diatomite, clay or a similar cheap substance. These formulations are generally prepared by dissolving Compound I in a suitable solvent and applying them to a granular carrier that has been preformed to the appropriate particle size in the range of about 0.5 to about 3 mm. A suitable solvent is a solvent in which Compound I is substantially or completely soluble. Such formulations can also be prepared by making a mass or paste of the vehicle and Compound I and solvent and crushing and drying to obtain the desired granular particle.

[0018] Powders containing Compound I can be prepared by thoroughly mixing Compound I in powder form with a suitable powdered agricultural vehicle, such as, for example, kaolin clay, ground volcanic rock and the like. Powders may suitably contain from about 1 to about 10 weight percent of Compound I based on the total weight of the powder.

[0019] The formulations may also contain adjuvant surfactants to enhance the deposition, wetting and penetration of Compound I in the target organism or culture. These surfactant adjuvants can optionally be used as a component of the formulation or as a tank mix. The amount of surfactant adjuvant will typically range from 0.01 to 1.0 volume percent based on the water spray volume, preferably 0.05 to 0.5 volume percent. Suitable adjuvant surfactants may include, but are not limited to, ethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols, salts of esters or sulfosuccinic acids, ethoxylated organosilicons, ethoxylated fatty amines or mixtures of surfactants with mineral or vegetable oils. The formulations may also include oil-in-water emulsions such as those disclosed in U.S. Patent Application Serial No. 11/495,228, the disclosure of which is expressly incorporated by reference herein.

[0020] In certain cases, it would be beneficial for Compound I formulations to be sprayed through an aerial application using aircraft or helicopters. The exact components of these aerial applications depend on the crop being treated. Aerial applications for vegetables use spray volumes preferably from 15 to 50 liters per hectare (L/ha) with the standard surfactant, wetting, adhering, spreading penetrating type additives such as non-ionic surfactants, organosilicones or oil plantation concentrates, preferably from 0.05 to 15 percent, based on a water spray volume.

[0021] The formulations may optionally include combinations that contain other pesticide compounds. These additional pesticidal compounds may be fungicides, insecticides, herbicides, nematocides, miticides, arthropodicides, bactericides, additives, such as non-ionic surfactants, organosilicons or crop oil concentrates or combinations thereof that are compatible with the compounds of the present invention in the medium. selected for application, and not antagonistic to the activity of the present compounds. Accordingly, in such embodiments, the other pesticide compound is used as a supplemental toxicant for the same pesticide or for a different pesticide use. Compound I and the pesticide compound in the combination may be present generally in a weight ratio of 1:100 to 100:1.

[0022] Compound I of the present description can also be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof. Compound I of the present disclosure is generally applied in conjunction with one or more other fungicides to control a wider variety of undesirable diseases. When used in conjunction with other fungicide(s), the currently claimed Compound I may be formulated with the other fungicide(s), tank mixed with the other fungicide(s). s) or applied sequentially with the other fungicide(s). These other fungicides may include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, ametoctradine, amisulbrom, antimycin, Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis, Bacillus subtilis strain QST713, benalaxyl, benomyl, bentiavalicarb isopropyl, benzylaminobenzene sulfonate salt (BABS), bicarbonates, biphenyl, bismerthiazole, bitertanol, bixafem, blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole, bupirimate, calcium polysulfide, Captafol, Captan, carbendazim, carboxine, carpropamide , carvone, clazafenone, chloroneb, chlorothalonil, clozolinate, Coniothyrium minitans, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), copper oxide, cyazofamide, cyflufenamide, cymoxanil, cyproconazole, cyprodinil , dazomet, debacarb, diammonium ethylenebis-(dithiocarbamate), diclofluanid, dichlorophene, diclocimet, diclomezine, dichlorane, diethofencarb, difenoconazole, diphenzoquat ion, diflumetrim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobutone, dinocape, diphenylamine, dithianone, dodemorph, dodemorph acetate, dodine, free base dodine, edifenfos, enestrobin, enestroburin, epoxiconazole, etaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fembuconazole, fenfuran, fenhexamide, fenoxanil, fempiclonil, fenpropidine, fenpropimorph, fenpyrazamine, fentin , fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph, fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl, fosetyl-aluminum , fuberidazole, furalaxyl, furametpyr, guazatine, guazatine acetates, GY-81, hexachlorobenzene, hexaconazole, himexazole, imazalil, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone, ipro benfos , iprodione, iprovalicarb, isoprothiolane, isopyrazam, isotianil, kasugamycin, kasugamycin hydrochloric hydrate, cresoxim-methyl, laminarin, mancobre, mancozeb, mandipropamide, maneb, mefenoxam, mepanipyrim, mepronil, meptil-dinocape, mercuric chloride, mercuric oxide, mercury chloride, metalaxyl, metalaxyl-M, metam, metam-ammonium, metam-potassium, metam-hodium, metconazole, metasulfocarb, methyl iodide, methyl isothiocyanate, metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrotal- isopropyl, nuarimol, octilinone, ofurace, oleic acid (fatty acids), orisastrobin, oxadixyl, oxina-copper, oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufem, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercury acetate, acid phosphonine, phthalide, picoxystrobin, polyoxin B, polyoxins, polyoxorim, potassium bicarbonate, hydroxyquinoline potassium sulfate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin, pyramethostrobin, pyraoxystrobin, pyrazophos, piribencarb, piributicarb, pyrifenoxy, pyrimethanil, pyriophenone, pyroquilone, quinoclamine, quinoxifene, quintazene, Reynoutria sachalinensis extract, sedaxan, sithiofame, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048 , tar oils, tebuconazole, tebufloquine, technazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolylfluanide, triadimephone, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triporin, triphenyl hydroxide tin, 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)phenyl thiocyanateme, aminopyrifem, ampropylphos, anilazine, azitiram, barium polysulfide , Bayer 32394, benodanil, benquinoxy, bentalurone, benzamacryl; benzamacril-isobutyl, benzamorph, benzovindiflupyr, binapacril, bis(methylmercury) sulfate, bis(tributyltin) oxide, butiobate, cadmium sulfate, calcium copper zinc chromate, carbamorph, CECA, clobenthiazone, chloraniformetane, chlorphenazole, chlorquinox, climbazole, bis( copper 3-phenylsalicylate), copper zinc chromate, coumoxystrobin, cufraneb, cupric hydrazinium sulfate, cuprobam, cyclafuramide, cipendazole, ciprofuram, decafentin, diclobentiazoxy, diclone, diclozoline, diclobutrazol, dimetirimol, dinoctom, dinosulfon, dinoterbom, dipimetitron, dipyrithione , dithalimphos, dodicine, drazoloxone, EBP, enoxastrobin, ESBP, etaconazole, etem, etirim, fenaminosulfe, fenaminstrobin, fenapanil, phenitropane, fenpicoxamide, fluindapyr, fluopimomide, fluotrimazole, fluphenoxystrobin, furcarbanil, furconazole, furconazole-cis, furmecycloxy, furophanate, gliodin , griseofulvin, halacrinate, Hercules 3944, hexylthiophos, ICIA0858, inpirfluxam, ipfentrifluconazole, ipflufenoquine, isofetamid, isoflucipram, isopamphos, isovaledione, mandestrobin, mebenil, mecarbinzid, mefentrifluconazole, metazoxolon, metfuroxam, methylmercury dicyandiamide , metsulfovax, methyltetraprol, milneb, mucochloric anhydride, myclozolin, N-3,5-dichlorophenyl-succinimide, N-3-nitrophenylitaconimide, natamycin, N-ethylmercury-4-toluenesulfonanilide, nickel bis(dimethydithiocarbamate), OCH, oxathiapiproline, phenylmercury dimethyldithiocarbamate, phenylmercury nitrate, phosdiphene, picarbutrazox, prothiocarb ; prothiocarb hydrochloride, pidiflumetofen, pyracarbolide, pyrapropoin, pyraziflumide, pyridaclomethyl, pyridinitrile, pyrisoxazole, pyroxychlor, piroxifur, quinacetol, quinacetol sulfate, quinazamide, quinconazole, quinofumeline, rabenzazole, salicylanilide, SSF-109, sultropene, tecoram, thiadifluor, titium hay, thiochlorfenfim, thiophanate, thioquinox, thioximide, triamiphos, triarimol, triazbutyl, triclamide, triclopiricarb, triflumezopyrim, urbacide, zarilamide and any combinations thereof.

[0023] Additionally, Compound I of the present invention can be combined with other pesticides, including insecticides, nematocides, miticides, arthropodicides, bactericides or combinations thereof, that are compatible with Compound I of the present invention in the medium selected for application, and non-antagonistic to the activity of Compound I to form mixtures of pesticides and synergistic mixtures thereof. Compound I of the present disclosure can be applied in conjunction with one or more other pesticides to control a wider variety of undesirable pests. When used in conjunction with other pesticides, the currently claimed Compound I may be formulated with the other pesticide(s), tank mixed with the other pesticide(s), or applied sequentially with the other pesticide(s). Typical insecticides include, but are not limited to: antibiotic insecticides such as alosamidine and thuringiensin; macrocyclic lactone insecticides such as spinosad and spinetoram; avermectin insecticides such as abamectin, doramectin, emamectin, eprinomectin, ivermectin and selamectin; milbemycin insecticides such as lepimectin, milbemectin, milbemycin oxime and moxidectin; carbamate insecticides such as bendiocarb and carbaryl; benzofuranyl methylcarbamate insecticides such as benfuracarb, carbofuran, carbosulfan, decarbofuran and furatiocarb; dimethylcarbamate insecticides such as dimitan, dimethylan, hiquincarb and pirimicarb; oxime carbamate insecticides such as alanicarb, aldicarb, aldoxycarb, butocarboxim, butoxycarboxim, methomyl, nitrilacarb, oxamyl, tazimcarb, thiocarboxime, thiodicarb and thiophanox; phenyl methylcarbamate insecticides such as allyloxycarb, aminocarb, bufencarb, butacarb, carbanolate, cloetocarb, dicresyl, dioxacarb, EMPC, ethiofencarb, fenetacarb, fenobucarb, isoprocarb, methiocarb, metolcarb, mexacarb, promacil, promecarb, propoxur, trimetacarb, XMC and xylylcarb ; desiccant insecticides such as boric acid, diatomaceous earth and silica gel; diamide insecticides such as broflanilide, chlorantraniliprole, cyantraniliprole, cyclaniliprole, cyalodiamide, flubendiamide, tetrachlorantraniliprole and tetraniliprole; diarylisoxazoline insecticides such as fluxametamide; dinitrophenol insecticides such as dinex, dinoprop, dinosam and DNOC; fluorine insecticides such as barium hexafluorosilicate, cryolite, sodium fluoride, sodium hexafluorosilicate and sulfluramide; formamidine insecticides such as amitraz, chloroform, formetanate and formparanate; fumigant 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, methylchloroform, methylene chloride, naphthalene, phosphine, sulfuryl fluoride and tetrachloroethane; inorganic insecticides such as borax, calcium polysulfide, copper oleate, mercurous chloride, potassium thiocyanate and sodium thiocyanate; chitin synthesis inhibitors such as bistrifluron, buprofezin, chlorfluazuron, cyromazine, diflubenzuron, flucicoxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron and triflumuron; juvenile hormone mimetics such as epofenonan, fenoxycarb, hydroprene, cynoprene, methoprene, pyriproxyfen and triprene; juvenile hormones such as juvenile hormone I, juvenile hormone II and juvenile hormone III; mesoionic insecticides such as dichloromezothiaz and triflumezopyrim; molting hormone agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide; molting hormones such as α-ecdysone and ecdysterone; molting inhibitors such as diophenolan; preconos such as precono I, precono II and precono III; unclassified insect growth regulators such as dicyclanil; nereistoxin analogue insecticides such as bensultap, cartap, thiocyclam and tiosultap; pyridylpyrazole insecticides such as ticlopyrazoflor; nicotinoid insecticides such as flonicamid; nitroguanidine insecticides such as clothianidin, dinotefuran, imidacloprid and thiamethoxam; nitromethylene insecticides such as nitempyram and nitazine; pyridimethylamine insecticides such as acetamiprid, cycloxaprid, imidacloprid, nitempram and thiacloprid; organochlorine insecticides such as bromo-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, isobenzan, isodrin, kelevan and mirex; organophosphate insecticides such as bromfenvinphos, chlorfenvinphos, crotoxiphos, dichlorvos, dicrotophos, dimethylvinphos, fospirate, heptenopes, methocrotophos, mevinphos, monocrotophos, naled, naphthalophos, fosamidon, propaphos, TEPP and tetrachlorvinphos; organothiophosphate insecticides such as dioxabenzophos, phosmethylylane and phenoate; aliphatic organothiophosphate insecticides such as acethione, amiton, cadusafos, chlorethoxyphos, chlormephos, demefione, demefione-O, demefione-S, demeton, demeton-O, demeton-S, demeton-methyl, demeton-O-methyl, demeton-S- methyl, demeton-S-methylsulfon, disulfoton, ethion, etoprophos, IPSP, isothioate, malathion, methacryphos, oxidemeton-methyl, oxideprophos, oxidisulfoton, phorate, sulfotep, terbufos and thiometon; aliphatic amide organothiophosphate insecticides such as amidithione, cyantoate, dimethoate, methyl ethoate, formotionin, mecarbam, omethoate, protoate, sofamide and vamidothion; oxime organothiophosphate insecticides such as chlorphoxim, phoxim and phoxim-methyl; heterocyclic organothiophosphate insecticides such as azamethiphos, coumaphos, coumitoate, dioxathione, endothione, menazon, morphothione, fossalone, pyraclophos, pyridafenthion and quinothione; benzothiopyrian organothiophosphate insecticides such as diticrophos and ticrophos; benzotriazine organothiophosphate insecticides such as azinphos-ethyl and azinphos-methyl; isoindole organothiophosphate insecticides such as dialyphos and phosmet; isoxazole organothiophosphate insecticides such as isoxathione and zolaprophos; pyrazolopyrimidine organothiophosphate insecticides such as chlorprazopes and pyrazophos; pyridine organothiophosphate insecticides such as chlorpyrifos and chlorpyrifos-methyl; pyrimidine organothiophosphate insecticides such as butathiofos, diazinon, ethrymphos, lyrinphos, pirimiphos-ethyl, pirimiphos-methyl, primidophos, pyrimitate and tebupirinphos; quinoxaline organothiophosphate insecticides such as quinalphos and quinalphos-methyl; thiadiazole organothiophosphate insecticides such as atidathione, litidathione, methidathione and protidathione; triazole organothiophosphate insecticides such as isazophos and triazophos; phenyl organothiophosphate insecticides such as nitrogenate, bromophos, bromophos-ethyl, carbophenothione, chlorthiophos, cyanophos, cythioate, dicapton, diclofenthion, etaphos, famfur, fenchlorphos, fenitrothion, fensulfothione, phenthion, phenthion-ethyl, heterophos, jodfenphos, mesulfenphos, parathion , parathion-methyl, fencapton, fosnichlor, profenofos, prothiophos, sulprophos, temephos, trichlormetaphos-3 and tripenophos; phosphonate insecticides such as butonate and trichlorfon; phosphonothioate insecticides such as mecarfon; phenyl ethylphosphonothioate insecticides such as phonofos and trichloronat; phenyl phenylphosphonothioate insecticides such as cyanofenphos, EPN and leptophos; phosphoramidate insecticides such as crufomate, fenamiphos, fosthiethane, mephospholane, phospholane and pyrimetaphos; phosphoramidothioate insecticides such as acephate, isocarbophos, isofenphos, isofenphosmethyl, methamidophos and propetanphos; phosphorodiamide insecticides such as dimefox, mazidox, mipafox and schradan; oxadiazine insecticides such as indoxacarb; oxadiazoline insecticides such as methexadiazone; phthalimide insecticides such as dialyphos, phosmet and tetramethrin; pyrazol insecticides such as tebufenpyrad, tolefenpyrad; phenylpyrazol insecticides such as acetoprol, etiprol, fipronil, pyrafluprole, pyriprole and vaniliprole; pyrethroid ester insecticides such as acrinatin, allethrin, bioalethrin, barthrin, bifenthrin, kappa-fifenthrin, bioethanometrin, chloropralethrin, cyclethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin , beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, dimefluthrin, dimethrin, empentrin, fenfluthrin, fenpyrithrin, fenpropathrin, fenvalerate, esfenvalerate, flucitrinate, fluvalinate, tau-fluvalinate, furethrin, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin , epsilon-metofluthrin, momfluorothrin, epsilon-momfluorothrin, permethrin, biopermethrin, transpermethrin, phenothrin, pralethrin, profluthrin, piresmethrin, resmethrin, bioresmethrin, cismethrin, tefluthrin, capatefluthrin, teralethrin, tetramethine, tetramethylfluthrin, tralomethrin and transfluthrin; pyrethroid ether insecticides such as etofenprox, flufenprox, halfenprox, protrifenbut and silafluofen; pyrimidine insecticides such as flufenerim and pyrimidifen; pyrrole insecticides such as chlorfenapyr; tetramic acid insecticides such as spiropidion and spiroetramat; tetronic acid insecticides such as spiromesiphene; thiourea insecticides such as diafenthiuron; urea insecticides such as flucofuron and sulcofuron; unclassified nematicides such as fluazaindolizine and thioxazafen; and unclassified insecticides such as benzpyrimozane, closantel, copper naphthalenate, crotamiton, EXD, fenazaflor, fenoxacrim, fluhexafon, flupirimin, hydramethylnon, isoprothiolane, malonobene, metaflumizone, nifluridede, oxazolsulfil, plifenate, pyridaben, pyridalyl, pyrifluquinazon, rafoxanide, sulfoxaflor, triaratene and triazamate and any combinations thereof.

[0024] Additionally, Compound I of the present invention can be combined with herbicides that are compatible with Compound I of the present invention in the medium selected for application, and not antagonistic to the activity of Compound I to form mixtures of pesticides and synergistic mixtures thereof . The fungicidal Compound I of the present disclosure can be applied in conjunction with one or more herbicides to control a wide variety of undesirable plants. When used in conjunction with herbicides, the currently claimed Compound I may be formulated with the herbicide(s), tank-mixed with the herbicide(s), or applied sequentially with the herbicide(s). Common herbicides include, but are not limited to: amide herbicides such as alidochlor, beflubutamide, benzadoxy, benzipram, bromobutide, cafenstrol, CDEA, ciprazole, dimethenamid, dimethenamid-P, diphenamide, epronaz, etnipromide, fentrazamide, flupoxam, falesafene, halosafen , isocarbamide, isoxaben, napropamide, naptalam, petoxamide, propyzamide, quinonamide, tebutam and thiafenacil; anilide herbicides such as chloranocril, cisanilide, clomeprop, cypromide, diflufenican, etobenzanide, fenasulam, flufenacet, flufenican, mefenacet, mefluidide, metamifop, monalide, naproanilide, pentanochlor, picolinaphene and propanil; arylalanine herbicides such as benzoylprope, flamprope and flamprope-M; chloroacetanilide herbicides such as acetochlor, alachlor, butachlor, butenachlor, delachlor, diethyl, dimethachlor, metazachlor, metolachlor, S-metolachlor, prethylachlor, propachlor, propisochlor, prenachlor, terbuchlor, tenylchlor and xylchlor; sulfonanilide herbicides such as benzofluoro, perfluidone, pyrimisulfan and profluazole; sulfonamide herbicides such as asulam, carbasulam, fenasulam and oryzalin; thioamide herbicides such as chlorthiamide; antibiotic herbicides such as bilanaphos; benzoic acid herbicides such as chlorambene, dicamba, 2,3,6-TBA and tricamba; pyrimidinyloxybenzoic acid herbicides such as bispiribac and piriminobac; pyrimidinylthiobenzoic acid herbicides such as prithiobac; phthalic acid herbicides such as chlorthal; picolinic acid herbicides such as aminopyralid, clopyralid, florpyraxifen, halauxifen and picloram; quinolinecarboxylic acid herbicides such as quinclorac and quinmerac; arsenical herbicides such as cacodylic acid, CMA, DSMA, hexaflurate, MAA, MAMA, MSMA, potassium arsenite and sodium arsenite; benzoylcyclohexanedione herbicides such as phenquinotrione, lancotrione, mesotrione, sulcotrione, tefuryltrione and tembotrione; benzofuranyl alkylsulfonate herbicides such as benfuresate and etofumesate; benzothiazole herbicides such as benzazoline; carbamate herbicides such as asulam, carboxazole chlorprocarb, dichlormate, fenasulam, carbylate and terbucarb; carbanylate herbicides such as barbano, BCPC, carbasulam, carbetamide, CEPC, chlorbufam, chlorpropam, CPPC, desmedifam, phenisofam, phenmedifam, phenmedifam-ethyl, profam and swep; cyclohexene oxime herbicides such as aloxidim, butroxydim, clethodim, cloproxidim, cycloxidim, profoxidim, sethoxydim, tepraloxidim and tralkoxidim; cyclopropyl isoxazole herbicides such as isoxachlortol and isoxaflutole; dicarboximide herbicides such as ethyl cynidone, flumezin, flumiclorac, flumioxazine and flumipropine; dinitroaniline herbicides such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, isopropaline, metalpropaline, nitralin, oryzalin, pendimethalin, prodiamine, profluralin and trifluralin; dinitrophenol herbicides such as dinofenate, dinoprope, dinosam, dinoseb, dinoterb, DNOC, etinophen and medinoterb; diphenyl ether herbicides such as ethoxyfen; nitrophenyl ether herbicides such as acifluorfen, aclonifen, bifenoxy, clomethoxyfen, chlornitrophen, etnipromide, fluorodifen, fluoroglycophene, fluoronitrophen, famasafene, furyloxifene, halosaphene, lactofen, nitrophene, nitrofluorfen and oxyfluorfen; dithiocarbamate herbicides such as dazomet and metam; halogenated aliphatic herbicides such as alorac, chloropone, dalapone, flupropanate, hexachloroacetone, iodomethane, methyl bromide, monochloroacetic acid, SMA and TCA; imidazolinone herbicides such as imazametabenz, imazamoxi, imazapic, imazapyr, imazaquine 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, chloroxynil, cyclopyranil, diclobenil, iodobonil, ioxynil and pyraclonil; organophosphate herbicides such as methyl amiprophos, anilophos, bensulide, bilanaphos, butamiphos, 2,4-DEP, DMPA, EBEP, fosamine, glufosinate, P-glufosinate, glyphosate and piperophos; phenoxy herbicides such as bromophenoxim, clomeprop, 2,4-DEB, 2,4-DEP, diphenopenten, disul, erbone, etnipromide, fenteracol and triphopsime; oxadiazoline herbicides such as methazol, oxadiargyl, oxadiazone; oxazole herbicides such as fenoxasulfone; phenoxyacetic herbicides such as 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl and 2,4,5-T; phenoxybutyric 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 clorazifop, clodinafop, clofop, cialofop, diclofop, fenoxaprop, fenoxaprop-P, fentiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapirifop, metamifop, propaquizafop, quizalofop, quizalofop-P and trifop; phenylenediamine herbicides such as dinitramine and prodiamine; pyrazole herbicides such as pyroxasulfone; benzoylpyrazole herbicides such as benzofenap, pyrasulfotol, pyrazolinate, pyrazoxifen, tolpiralate, and topramezone; phenylpyrazole herbicides such as fluazolate, niporaclofen, pioxadem and pyraflufen; pyridazine herbicides such as credazine, cyclopyrimorate, pyridafol and pyridate; pyridazinone herbicides such as brompyrazone, chloridazone, dimidazone, flufenpyr, metflurazone, norflurazone, oxapyrazone and pidanone; pyridine herbicides such as aminopyralid, cliodinate, clopyralid, dithiopyr, florpyrauxifem, fluroxypyr, halauxifem, haloxidine, picloram, picolinafen, pyrichlor, thiazopyr and triclopyr; pyrimidinediamine herbicides such as iprimidam and tioclorim; quaternary ammonium herbicides such as cyperquat, diethquat, diphenzoquat, diquat, morphamquat and paraquat; thiocarbamate herbicides such as butylate, cycloate, dialate, EPTC, esprocarb, ethiolate, isopolinate, methiobencarb, molinate, orbencarb, pebulate, prosulfocarb, pyributicarb, sulfate, thiobencarb, thiocarbazil, triallate and vernolate; thiocarbonate herbicides such as dimexane, EXD and proxane; thiourea herbicides such as methiurone; triazine herbicides such as dipropetrin, indaziflam, triaziflam and trihydroxytriazine; chlorotriazine herbicides such as atrazine, chlorazine, cyanazine, cyrazine, eglinazine, ipazine, mesoprazine, procyazine, proglinazine, propazine, sebuthylazine, simazine, terbuthylazine and triethazine; methoxytriazine herbicides such as atratone, metometone, prometone, secbumetone, simetone and terbumetone; methylthiotriazine herbicides such as ametrine, aziprothrin, cyanatrin, desmethrin, dimethethrin, metoprothrin, promethrin, simethrin and terbutrin; triazinone herbicides such as ametridione, amibuzin, hexazinone, isomethiozin, metamitrone, metribuzin, and trifludimoxazin; triazole herbicides such as amitrol, cafenstrol, epronaz and flupoxam; triazolone herbicides such as amicarbazone, bencarbazone, carfentrazone, flucarbazone, ipfencarbazone, propoxycarbazone, sulfentrazone and methyl thiencarbazone; triazolopyrimidine herbicides such as cloransulam, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam and piroxsulam; uracil herbicides such as benzfendizone, bromacil, butafenacil, flupropacil, isocil, lenacil, saflufenacil and terbacil; urea herbicides such as benzthiazurone, cumylurone, cyclolurea, dichloralurea, diflufenzopyr, isonorurone, isourone, metabenzthiazurone, monisourone and norurone; phenylurea herbicides such as anisuron, buturone, chlorbromurone, chlorethurone, chlorotolurone, chloroxurone, daimurone, difenoxuron, dimefurone, diuron, fenurone, fluometurone, fluothiurone, isoproturone, linurone, methiurone, methyldimrone, methobenzuron, metobromurone, methoxurone, monolinuron, monuro na, neburone , paraflurone, phenobenzurone, sidurone, tetraflurone and thidiazurone; azimsulfuron, bensulfurone, ethoxysulfuron, flazasulfuron, foramsulfuron, halosulfuron, metazosulfuron, nicosulfuron, primisulfuron, propyrysulfuron, sulfometurone, sulfosulfuron and triazinylsulfonylurea herbicides such as etametsulfuron, iodosulfuron, amidosulfuron, chlorimuron, cyclosulfamurone, flucetosulfuron na, flupyrsulfuron, imazosulfuron, mesosulfuron, orthosulfamurone, oxasulfuron , pyrazosulfuron, rimsulfuron, trifloxysulfuron; herbicides of chlorsulfuron, cinosulfuron, iofensulfuron, metsulfuron, prosulfuron, thifensulfuron, triasulfuron, tribenurone, triflusulfuron and tritosulfuron; thiadiazolylurea herbicides such as butyurone, ethydimurone, tebuthiurone, thiazaflurone and thidiazurone; and unclassified herbicides such as acrolein, allyl alcohol, aminocyclopyrachlor, azafenidine, bentazone, benzobicyclone, biciclopyrone, butidazole, calcium cyanamide, cambendichlor, chlorfenac, chlorfenprop, chlorflurazol, chlorflurenol, cinmethylin, clomazone, CPMF, cresol, cyanamide, cyclopyrimorate, ortho-dichlorobenzene, dimepiperate, endothal, fluoromidine, fluridone, flurochloridone, flurtamone, fluthiacet, indanofam, methyl isothiocyanate, OCH, oxaziclomephone, pentachlorophenol, pentoxazone, phenylmercury acetate, prosulfalin, pyribenzoxim, pyrifthalide, quinoclamine, rodetanil, sulglicapine, thidiazi mine, tridiphane, trimeturone, tripropyndan and tritac.

[0025] Compound I of the present invention can also comprise or can be applied together and/or sequentially with more active compounds. These additional compounds may be plant health stimulants, such as organic compounds, inorganic fertilizers, or micronutrient donors or other preparations that influence plant growth, such as inoculants.

[0026] In another embodiment, Compound I may also comprise or may be applied together and/or sequentially with other biological organisms, such as, but not limited to, 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 exhibited activity against insects, mites , nematodes, and/or phytopathogens.

[0027] One embodiment of the present description is a method of controlling or preventing fungal attack. This method comprises applying to the soil, plant, roots, foliage, seed or site of the fungus, or to a site at which infestation is to be prevented (e.g., application to cereals or vines), an effective fungicidal amount of Compound I. Compound I is suitable for treating various plants at fungicidal levels, while having low phytotoxicity. Compound I may be useful in both a protective and/or eradicant manner.

[0028] Compound I was found to have a significant fungicidal effect particularly for agricultural use. The Formula I compound is particularly effective for use with agricultural crops and horticultural plants. Additional benefits may include, but are not limited to: improving the health of a plant; improve the yield of a plant (e.g. greater biomass and/or higher content of valuable ingredients); improve the vigor of a plant (e.g., better plant growth and/or greener leaves); improve the quality of a plant (for example, better content or composition of certain ingredients); and improve the plant's tolerance to abiotic and/or biotic stress.

[0029] In particular, the composition is effective in controlling a variety of undesirable fungi that infect useful vegetables. The composition can be used against a variety of Ascomycete and Basidiomycete fungi, including, for example, the following representative fungal species:

[0030] In cucurbits: powdery mildew (Erysiphe cichoracearum, Esfinqueca fulignea), circular spot (Mycosphaerella brassicicola), black foot (Plenodomus lingam), anthracnose (Colletotrichum higginsianum, Colletotrichum obiculare, Colletotrichum spp., Glomerella lagenarium), gummy stem blight ( Mycosphaerella melonis, Didymella bryoniae, Stagonosporopsis cucurbitacearum); Alternaria leaf spot and blight (Alternaria cucumerina, Alternaria alternata f. sp. cucurbitae, Alternaria spp.), Cercospora leaf spot (Cercospora citrullina, Cercospora spp.), fusariosis (Fusarium oxysporum), root rot (Rhizoctonia solani), Corynespora target/blight (Corynespora cassiicola), scab (Cladosporium cucumerinum), Verticillium wilt (Verticillium dahliae, Verticillium albo-atrum), black root rot (Thielaviopsis basicola), blue mold rot (Penicillium spp.), charcoal rot (Macrophomina phaseolina), and crater rot (fruit) (Myrothecium roridum);

[0031] In tomatoes: powdery mildew (Leveillula taurica), Septoria leaf spot (Septoria lycopersici), white mold (Sclerotinia sclerotiorum, Sclerotinia minor), target spot (Corynespora cassiicola), neck rot (Sclerotium rolfsii), gray mold (Botrytis cinerea), gray leaf spot (Stemphylium spp.), fusariosis, Fusarium root and crown rot (Fusarium oxysporum), anthracnose (Colletotrichum coccodes, Colletotrichum dematium, Colletotrichum gloeosporioides, Glomerella cingulate), stem canker and Alternaria black mold ( Alternaria alternata), black root rot (Chalara elegans), Cercospora leaf mold (Cercospora fuligena), charcoal rot (Macrophomina phaseolina), root suberosis (Pyrenochaeta lycopersici), Didymella stem rot (Didymella lycopersici), black spot (Alternaria solani), leaf mold (Passalora fulva, Mycovellosiella fulva), phoma rot (Phoma destructiva) and acid rot (Geotrichum candidum);

[0032] In leafy vegetables: Cercospora leaf spot (Cercospora longissimi, Cercospora spp.), gray mold/botrytis rot (Botrytis cinerea), Alternaria leaf spot and blight (Alternaria sonchi, Alternaria spp.), powdery mildew (Erysiphe cichoracearum , Golovinomyces cichoracearum, Uncinula spp.), rust (Puccinia dioicae), Septoria leaf spot (Septoria lactucae, Septoria spp.), collar rot (Sclerotium rolfsii), basal rot (Phoma exigua), Rhizoctonia bottom rot (Rhizoctonia solani ), Sclerotinia drop (Sclerotinia minor, Sclerotinia sclerotiorum) and Stemphylium leaf spot (Stemphylium botryosum);

[0033] On potatoes: anthracnose or black spot (Colletotrichum coccodes), brown spot and dark hole (Alternaria alternata), Cercospora leaf spot (Cercospora concors), charcoal rot (Macrophomina phaseolina), common rust (Puccinia pittieriana), rust deformation (Aecidium cantensis), black spot (Alternaria solani), Fusarium and fusariouse dry rot (Fusarium spp.), gangrene (Phoma exigua f. sp. foveata), gray mold (Botrytis cinerea), black spot or Phoma leaf spot (Stagonosporopsis andigena, Phoma andigena var. andinai), powdery mildew (Erysiphe cichoracearum), Rhizoctonia canker and black scab (Rhizoctonia solani), Rosellinia black rot (Rosellinia spp), Septoria leaf spot (Septoria lycopersici var. malagutil), scab silvery blight (Helminthosporium solani), bark spot (Polissittalum pustulans), stem rot (Sclerotium rolfsii), potato smut (Thecaphora smut) (Tecaphora solani), Ulocladium blight (Ulocladium atrum), Verticillium wilt (Verticillium albo-atrum ) and white mold (Sclerotinia sclerotiorum);

[0034] In peppers: collar rot (Sclerotium rolfsii), powdery mildew (Leveillula taurica), anthracnose (Colletotrichum capsici, Colletorichum acutatum, Colletorichum spp.), Cercospora leaf spot (frog eye) (Cercospora capsici, Cercospora spp.) , charcoal rot (Macrophomina phaseolina), damping-off and root rot (Rhizoctonia solani), Fusarium stem rot (Fusarium solani), fusariouse (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] In Brassica crops: leaf spot and black spot of Alternaria (Alternaria brassicicola, Alternaria spp.), Anthracnose (Colletotrichum spp.), black cinnamon (Leptosphaeria maculans, Phoma lingam), leaf spot of Cercospora (Cercopsora spp.) , Fusarium yellowing and other diseases (Fusarium spp.), Botrytis gray mold/spot (Botrytis cinerea), powdery mildew (Erysiphe polygoni), Rhizoctonia rot and spot (Rhizoctonia solani), ring spot (Mycosphaerella brassicicola), Sclerotinia rot (Sclerotinia spp.), white leaf spot (Pseudocercosporella capselare).

[0036] It was found that Compound I has significant fungicidal effects on phytopathogenic fungi of agriculturally useful vegetables. These diseases include Alternaria brassicicola, which causes black leaf spot on cabbage; Alternaria solani, which causes large black spot on tomatoes; Sclerotinia sclerotiorum, which causes sclerotinia rot of lettuce; Colletotrichum capsici, which causes pepper anthracnose; Erysiphe cichoracearum, which causes cucumber powdery mildew; Mycovellosiella fulva, which causes tomato leaf mold; Stagonosporopsis cucurbitacearum, which causes gummy blight on watermelons; and Botrytis cinerea, which causes gray mold on broad beans, particularly for agricultural use. Compound I is particularly effective for use on agricultural crops and horticultural plants.

[0037] Compound I has a wide range of effectiveness as a fungicide. The exact amount of active material to be applied depends not only on the specific active material being applied, but also on the specific action desired, the fungal species that must be controlled and the stage of their growth, as well as the part of the plant or of another product that must come into contact with the compound. Therefore, Compound I and formulations containing it may not be equally effective in similar concentrations or against the same fungal species.

[0038] Compound I is effective for use on plants in a disease-inhibiting and phytologically acceptable amount. The term "disease-inhibiting and phytologically acceptable amount" refers to an amount of a compound that kills or inhibits the plant disease for which control is desired, but that is not significantly toxic to the plant. This amount will generally be from about 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm being preferred. The exact concentration of compound required varies with the fungal disease being controlled, the type of formulation used, the method of application, the specific plant species, weather conditions, and the like. An appropriate application rate typically ranges from about 0.10 to about 4 pounds/acre (about 0.01 to 0.45 grams per square meter, g/m2).

[0039] Any desired range or value mentioned in this document can be extended or changed without losing the intended effects, as is evident to those skilled in the art to understand the teachings contained in this document. Examples:

Field evaluation of Alternaria brassicicola (ALTEBI) in cabbage:

[0040] A fungicidal treatment containing Compound I, applied in a 5% EC formulation and tank-mixed with an adjuvant (Trycol, 50% w/w to 0.2% v/v) was sprayed three times on cabbage plants (BRSOL) with the first application during cabbage LF stage 10-12. The following applications were made at 7-day intervals, all applications being sprayed at rates of 50, 100 and 150 grams of active ingredient per hectare (g ai/ha). The experimental batches were inoculated with black leaf spot pathogen 2 days after the first application. The treatment was part of an experimental trial designed as a randomized complete block with four replications and a batch size of approximately 2 x 1 m, with Compound I being applied to a water volume of 800 L/ha.

[0041] Disease severity was assessed as the percentage of diseased area of cabbage base foliage infected (6 plants per batch randomly). Visual infection was assessed three times during the trial within 7 days after each application. The area under the disease progress curve (AUDPC) was calculated for each batch using the recorded severity datasets. Relative AUDPC (% control based on AUDPC) was calculated as percentage of untreated control. The results are provided in Table 1.

Field evaluation of Sclerotinia sclerotiorum (SCLESC) in lettuce:

[0042] A fungicidal treatment containing a 5% EC formulation of Compound I plus an adjuvant (Trycol, 50% w/w in 0.2% v/v), was sprayed on cabbage lettuce plants (LACSC) twice , the first application during head formation 36 days after planting, and the second application 7 days later. Compound I formulations were applied at rates of 50, 100 and 150 grams of active ingredient per hectare (g ai/ha). Experimental batches were inoculated with sclerotinia rot pathogen 2 days after the first application. The treatment was part of an experimental trial designed as a randomized complete block with four replications and a batch size of approximately 2 x 1 m, with Compound I formulations being applied to a water volume of 800 L/ha.

[0043] The percentage of disease infection was calculated by the equation (stem lesion lengths)/(total stem lengths) x 100% per plant (6 plants per batch randomly). Sclerotinia infection was assessed four times, 7 days after application A (DAAA) plus 7, 14 and 21 DAAB. The area under the disease progress curve (AUDPC) was calculated for each batch using the recorded visual infection datasets. Relative AUDPC (% control based on AUDPC) was calculated as percentage of untreated control. The results are provided in Table 1.

Field assessment of Colletotrichum capsici (COLLCA) in peppers:

[0044] The evaluation of COLLCA Compound I in peppers, both protectively and curatively, was carried out in two separate field trials. For the 2-day protection test, a fungicidal treatment containing a 5% EC formulation of Compound I plus an adjuvant (Trycol, 50% w/w to 0.2% v/v) was sprayed on pepper plants (CPSAN ) three times, the first application during flowering and fruiting 43 days after planting, with subsequent applications at intervals of 7 days. Compound I formulations were applied at rates of 50, 100 and 150 grams of active ingredient per hectare (g ai/ha). The experimental batches were inoculated with the anthracnose pathogen 2 days after the first application. The treatment was part of an experimental trial designed as a randomized complete block with four replications and a batch size of approximately 2 x 1 m, with Compound I formulations being applied to a water volume of 1000 L/ha.

[0045] The severity of the disease was evaluated as a percentage of the diseased area of the fruits per plant (6 plants per batch randomly). Anthracnose infection was assessed four times, 7 days after application A (DAAA), 7 DAAB, plus 7 and 14 DAAC. The area under the disease progress curve (AUDPC) was calculated for each batch using the recorded visual infection datasets. Relative AUDPC (% control based on AUDPC) was calculated as percentage of untreated control. The results are provided in Table 1.

[0046] For the 4-day curative trial, a fungicidal treatment containing a 5% EC formulation of Compound I plus an adjuvant (Trycol, 50% w/w to 0.2% v/v) was sprayed on pepper plants (CPSAN) twice, the first application during flowering and fruiting 59 days after planting, with the second application after 7 days. Compound I formulations were applied at rates of 50, 100, 150 and 200 grams of active ingredient per hectare (g ai/ha). The experimental batches were inoculated with the anthracnose pathogen 4 days before the first application (curative). The treatment was part of an experimental trial designed as a randomized complete block with four replications and a batch size of approximately 2 x 1 m, with Compound I formulations being applied to a water volume of 1200 L/ha.

[0047] The severity of the disease was evaluated as a percentage of the diseased area of the fruits per plant (6 plants per batch randomly). Anthracnose infection was assessed four times, 7 days after application A (DAAA), plus 7, 14 and 21 DAAB. The area under the disease progress curve (AUDPC) was calculated for each batch using the recorded visual infection datasets. Relative AUDPC (% control based on AUDPC) was calculated as percentage of untreated control. The results are provided in Table 1.

Field evaluation of Erysiphe cichoracearum (ERYSCI) in cucumber:

[0048] The evaluation of ERYSCI Compound I in cucumbers, in a protective and curative manner, was carried out in two separate field trials. For the two-day protection test (2DP), a fungicidal treatment containing a 5% EC formulation of Compound I plus an adjuvant (Trycol, 50% w/w to 0.2% v/v) was sprayed on crop plants. cucumber (CUMSA) twice, the first application during fruiting 41 days after planting, with the next application after 7 days. Compound I formulations were applied at rates of 50, 100 and 150 grams of active ingredient per hectare (g ai/ha). The experimental batches were inoculated with the powdery mildew pathogen 2 days after the first application. The treatment was part of an experimental trial designed as a randomized complete block with four replications and a plot size of approximately 2 x 1 m, with Compound I formulations being applied to a water volume of 1200 L/ha based on seedling size. .

[0049] Disease severity was assessed as a percentage of the diseased area of infected cucumber foliage per plant (6 plants per batch randomly). Cucumber powdery mildew infection was assessed three times, 7 days after application A (DAAA) and 7 and 14 DAAB. The area under the disease progress curve (AUDPC) was calculated for each batch using the recorded visual infection datasets. Relative AUDPC (% control based on AUDPC) was calculated as percentage of untreated control. The results are provided in Table 1.

[0050] In the curative trial, a fungicidal treatment containing a 5% EC formulation of Compound I plus an adjuvant (Trycol, 50% w/w to 0.2% v/v) was sprayed on cucumber plants (CUMSA) two times, the first application during fruiting 29 days after planting, with the second application after 7 days. Compound I formulations were applied at rates of 50, 100 and 150 grams of active ingredient per hectare (g ai/ha). The experimental batches were inoculated with the powdery mildew pathogen 2 days before the first application (curative). The treatment was part of an experimental trial designed as a randomized complete block with four replications and a plot size of approximately 2 x 1 m, with Compound I formulations being applied to a water volume of 1200 L/ha based on seedling size. .

[0051] Disease severity was assessed as a percentage of the diseased area of infected cucumber foliage per plant (6 plants per batch randomly). Powdery mildew disease severity was assessed four times, 7 days after application A (DAAA), plus 7, 14 and 21 DAAB. The area under the disease progress curve (AUDPC) was calculated for each batch using the recorded visual infection datasets. Relative AUDPC (% control based on AUDPC) was calculated as percentage of untreated control. The results are provided in Table 1.

Field evaluation of Alternaria solani (ALTESO) in tomato:

[0052] The evaluation of ALTESO Compound I in tomato was carried out in two separate field trials. In the first trial, a fungicidal treatment containing Compound I, applied in a 5% and 10% SC formulation and tank-mixed with an adjuvant (Agnique BP420, 50% w/w to 0.3% v/v) was sprayed on tomato plants (LYPES) approximately 60-70 cm high at rates of 100 and 200 grams of active ingredient per hectare (g ai/ha). The trial was based on five foliar applications at 7-day intervals with inoculation with large black spot pathogen 2 days after the first application. The treatment was part of an experimental trial designed as a randomized complete block with four replications and a plot size of approximately 1.5 x 4 m. Compound I was applied to a water volume of 1000 L/ha with an AZO backpack sprayer using compressed air.

[0053] The severity of the disease was recorded as a percentage of the diseased area in a random selection of 20 leaves and 20 fruits per batch. The percentage of control was evaluated with 6 assessments made between 0-35 days after the first application, DAA1. The area under the disease progress curve (AUDPC) was calculated for each batch using the recorded severity datasets. Relative AUDPC (% control based on AUDPC) was calculated as percentage of untreated control. The results are provided in Table 2.

[0054] In a replicated trial, a fungicidal treatment containing Compound I, applied in a 5% and 10% SC formulation and tank mixed with an adjuvant (Agnique BP420, 50% w/w to 0.3% v/v ) was sprayed on tomato plants (LYPES, Taylor variety) approximately 21 days after planting. Compound I formulations were applied at rates of 100 and 200 grams of active ingredient per hectare (g ai/ha). The trial was based on six foliar applications at 10-day intervals under natural tomato early blight disease pressure. The treatment was part of an experimental trial designed as a randomized complete block with four replications and a plot size of approximately 2 x 4 m. Compound I formulations were applied to a water volume of 800 L/ha using a backpack batch sprayer (BKPCKENG, Solo 443; HCSOLID - Albutz ATR80 Orange Nozzle) and pressurized to 300 kPa. Disease severity (percent control) was recorded as percentage of visual leaf infection per batch and was assessed at 10 days after the last application. The results are provided in Table 2.

Field evaluation of Mycovellosiella fulva (FULVFU) in tomato:

[0055] A 10% SC formulation of Compound I was mixed with four different adjuvants: BP420 Agnique (50% w/w to 0.3% v/v); Trycol (50% w/w to 0.1% v/v); Etomeen T18H (50% w/w to 0.2% v/v); and Phase II (50% w/w to 0.2% v/v). A fungicide treatment containing formulations of Compound I, alone or with adjuvants, was sprayed on tomato plants four times, the first application approximately 3 months after planting, with the following three applications at 7-10 day intervals. Compound I formulations were applied at rates of 50, 100, 150 and 200 grams of active ingredient per hectare (g ai/ha). The experimental batches were inoculated with leaf mold pathogen 7 days before the first application (curative). The treatment was part of an experimental trial designed as a randomized complete block with four replications and a plot size of approximately 2.5 x 1.4 m. Compound I formulations were applied to a water volume of 675 L/ha.

[0056] Disease severity was recorded as a percentage of visibly diseased foliage (6 random plants per batch). Tomato leaf mold infection was assessed five times within 7 days after the first application (7 DAAA), 7 DAAB, 5 DAAC, followed by 7 and 12 DAAD. The area under the disease progress curve (AUDPC) was calculated for each batch using the recorded severity datasets. Relative AUDPC (% control based on AUDPC) was calculated as percentage of untreated control. The results are provided in Table 3.

Field evaluation of Stagonosporopsis cucurbitacearum (DIDYBR) in watermelon:

[0057] A 10% SC formulation of Compound I was mixed with four different adjuvants: BP420 Agnique (50% w/w to 0.3% v/v); Trycol (50% w/w to 0.1% v/v); Etomeen T18H (50% w/w to 0.2% v/v); and Phase II (50% w/w to 0.2% v/v). A fungicide treatment containing formulations of Compound I, alone or with adjuvants, was sprayed on watermelon plants four times, the first application approximately 2 months after planting, with the following three applications at 7-10 day intervals. Compound I formulations were applied at rates of 50, 100, 150 and 200 grams of active ingredient per hectare (g ai/ha). The experimental batches were inoculated with the gummy stem blight pathogen 2 days after the first application. The treatment was part of an experimental trial designed as a randomized complete block with four replications and a plot size of approximately 2.5 x 1.4 m. Compound I formulations were applied to a water volume of 675 L/ha.

[0058] Disease severity was recorded by the length of the stem lesion and as a percentage of diseased foliage (3 random plants per batch). Watermelon stem gummy blight infection was assessed twice, the first at 6 days after the first application (6 DAAA), followed by 19 DAAD. The area under the disease progress curve (AUDPC) was calculated for each batch using the recorded severity datasets. Relative AUDPC (% control based on AUDPC) was calculated as percentage of untreated control. The results are provided in Table 4.

Greenhouse assessment of Botrytis cinerea (BOTRCI) in broad bean:

[0059] The technical grades of the materials were dissolved in acetone, and were then mixed with nine volumes of water containing 100 ppm of Triton X-100. Fungicide formulations were applied to plant seedlings using an automated run-off booth sprayer. All sprayed plants were allowed to dry before further handling. Test plants were inoculated with Botrytis cinerea 1 day after application. When disease symptoms were fully expressed in untreated plants, the percentage of diseased area of the plant was rated on a scale of 0 to 100 percent disease severity. The percentage of disease control was calculated using the ratio of disease severity in treated plants to untreated plants. The results are provided in Table 5.

[0060] In each case of Tables 1-5 the control percentage rating scale based on AUDPC is as follows: Table 1: Percentage of control by Compound Ia on Fungal Diseases of Plants Based on Area Under the Disease Progression Curve (AUDPC) in Protective and Curative Trials. aCompound I applied as a 5% EC formulation with Trycol adjuvant (50% w/pa 0.2% v/v) bBlack leaf spot of cabbage - Alternaria brassicicola cSclerotinia rot of lettuce - Sclerotinia sclerotiorum dAnthracnose of pepper - Colletotrichum capsici and Cucumber powdery mildew - Erysiphe cichoracearum fGrams of active ingredient per hectare g2 days of protection h4 days of cure Table 2: Efficacy of Compound Ia against Large Black Spot (ALTESO, Alternariasolani) on Tomato Leaves and Fruits in EC and SC Formulations . aCompound I applied with Agnique BP420 (50% w/pa 0.3% v/v) as an adjuvant bPercentage of disease control on tomato leaves based on Area Under the Disease Progression Curve (AUDPC) cPercentage of disease control disease in tomato fruits based on Area Under the Disease Progression Curve (AUDPC) dGrams of active ingredient per hectare Table 3: Efficacya of Compound I against Tomato Leaf Mold (FULVFU, Mycovellosiella fulva) in a SC Formulation at 10% with or without Adjuvants. aPercentage of control based on Area Under the Disease Progression Curve (AUDPC) bGrams of active ingredient per hectare cI - No adjuvant dII - Agnique BP420 (50% w/pa 0.3% v/v) eIII - Trycol (50 % w/pa 0.1% v/v) fIV - Etomeen T18H (50% w/pa 0.2% v/v) gV - Phase II (50% w/pa 0.2% v/v) Table 4 : Efficacy of Compound I against gummy blight of watermelon stem (DIDYBR, Stagonosporopsis cucurbitacearum) in a 10% SC formulation with or without adjuvants. aPercentage of control based on Area Under the Disease Progression Curve (AUDPC) bGrams of active ingredient per hectare cI - No adjuvant dII - Agnique BP420 (50% w/pa 0.3% v/v) eIII - Trycol (50 % w/pa 0.1% v/v) fIV - Etomeen T18H (50% w/pa 0.2% v/v) gV - Phase II (50% w/pa 0.2% v/v) Table 5 : Efficacy of Compound I against Fava Bean Gray Mold (BOTRCI, Botrytis cinerea). aParts per million bPercentage of control calculated using the ratio of disease severity in treated plants to untreated plants

Field assessment of Corynespora cassiicola (CORYCA) in tomato:

[0061] A fungicidal treatment containing Compound I applied in a SC formulation (embedded MSO) and tank mixed with an adjuvant (Agnique BP-420, 50% w/w in 0.2% v/v or Adsee C80W 80% ), was sprayed on tomato plants (LYPES, Charger variety) at the BBCH64 growth stage (4th flower opening) at rates of 50, 75, 100 and 150 grams of active ingredient per hectare (g ai/ha) in two trials. Experimental batches were inoculated with the target spot pathogen one day after initial application. The treatment was part of an experimental trial designed as a randomized complete block (RCB) with four replications and an approximately 6 x 25 foot (ft) plot. Compound I was applied in a water volume of 100 gallons per acre (gal/acre), using a tractor sprayer (SCDISC D1 Nozzles) and was pressurized to 200 psi.

[0062] Disease severity (percentage of visibly diseased foliage (leaf) in the entire batch) was assessed four times during the trial (1-20 days after application, DAA). The area under the disease progress curve (AUDPC) was calculated for each batch using the recorded severity datasets. Relative AUDPC (% control based on AUDPC) was calculated as percentage of untreated control. The results are provided in Table 6.

Field Assessment of Colletotrichum Coccodes (COLLCA) on Tomato:

[0063] A fungicidal treatment containing Compound I applied in a SC formulation (embedded MSO) and tank mixed with an adjuvant (Agnique BP-420, 50% w/w in 0.2% v/v or Adsee C80W 80% ), was sprayed on tomato plants (LYPES, variety Roma VS type Saladette) at growth stage 12 in vegetative growth at rates of 50, 75, 100 and 150 grams of active ingredient per hectare (g ai/ha) in two trials . The experimental batches were run with natural infestation of the anthracnose pathogen and supplemented with additional inoculum approximately one day after the 1st application. The treatment was part of a trial designed as a randomized complete block (RCB) with four replications and a plot size of approximately 6.67 x 30 feet. Compound I was applied to 40 gal/acre water volume using a carbon dioxide (CO2) backpack sprayer (Nozzles 8004VS FF) and pressurized to 38 psi.

[0064] The percentage of leaf severity was evaluated three times during the test (0-23 days after application 1). The area under the disease progress curve (AUDPC) was calculated for each batch using the recorded leaf severity data. Relative AUDPC (% control based on AUDPC) was calculated as percentage of untreated control. The results are provided in Table 7. Table 6: Comparison of Compound I Formulation with MSO or Tank Mixed with Agnique BP-420 of the Calculated Percent Control of Tomato Target Spot (CORYCA, Corynespora cassiicola) aRate in g/ha bRate in mL/ha Table 7: Comparison of the Formulation of Compound I with MSO or Tank Mixed with Agnique BP-420 of the Calculated Percent Control of Tomato Anthracnose (COLLCA, Colletotrichum coccodes) aRate in g/ha bRate in mL/ha

Claims (2)

1. Method for controlling fungal diseases in vegetable crops selected from cucurbits, tomatoes, leaf vegetables, potatoes, peppers and broad beans, which are at risk of presenting the disease, characterized by the fact that it comprises the steps of: contacting at least one part of a plant and/or an area adjacent to a plant with compound I or with a composition comprising compound I wherein said compound is effective against a plant pathogen and wherein said fungal pathogen is selected from the group consisting of the causal agents of: dark leaf spot on cabbage (Alternaria brassicicola), lettuce rot caused by Sclerotinia (Sclerotinia sclerotiorum) , anthracnose of hot peppers (Colletotrichum capsici), tomato leaf mold (Mycovellosiella fulva), gummy stem blight on watermelon (Stagonosporopsis cucurbitacearum) and gray mold on faba bean (Botrytis cinerea), target spot/Corynespora blight (Corynespora cassiicola), and Tomato Anthracnose (Colletotrichum coccodes). 2. Method according to claim 1, characterized in that the composition further comprises at least one additional agriculturally active ingredient selected from the group consisting of: an insecticide, a herbicide and a fungicide.