KR102555135B1 - Use of acyclic picolinamide compounds as fungicides for control of plant pathogenic fungi in vegetables - Google Patents

Abstract

The present disclosure relates to the field of agrochemistry, including COMPOUND I and its use for controlling fungal diseases in agriculturally useful vegetable crops.

Description

Use of acyclic picolinamide compounds as fungicides for control of plant pathogenic fungi in vegetables

CROSS REFERENCES TO RELATED APPLICATIONS

This application claims the benefit of US Provisional Patent Application Serial No. 62/500172, filed May 2, 2017, expressly incorporated herein by reference.

technology field

The present disclosure relates to ( S )-1,1-bis(4-fluorophenyl)propan-2-yl (3-acetoxy-4-methoxypicolinoyl) -L- for controlling fungal disease in vegetables. It relates to the field of use of alaninate.

Fungicides are compounds of natural or synthetic origin that act to protect and heal plants against damage caused by agriculturally related fungi. Generally, no single fungicide is useful in all situations. As a result, research is ongoing to produce fungicides that may have better performance, are easier to use, and are less expensive.

The present disclosure provides ( S )-1,1-bis(4-fluorophenyl)propan-2-yl(3-acetoxy-4-methoxypicolinoyl) -L -alaninate (Compound I) as a fungicide. and its uses. Compound I can provide protection against ascomycetes, basidiomycetes and deuteromycetes.

One embodiment of the present disclosure includes a method of controlling a pathogen-induced disease in a plant at risk from a pathogen comprising contacting the plant or an area adjacent to the plant with a composition comprising Compound I.

Another embodiment of the present disclosure is the protection of plants against attack by phytopathogenic organisms, comprising applying Compound I, or a composition comprising Compound I, to soil, plants, plant parts, leaves and/or seeds. or the use of compounds I for the treatment of plants infected by phytopathogenic organisms.

Additionally, another embodiment of the present disclosure is a composition useful for protecting plants against attack by phytopathogenic organisms and/or treating plants infected by phytopathogenic organisms comprising Compound I and a botanically acceptable carrier material. am.

One exemplary embodiment of the present disclosure includes a mixture for controlling the growth of fungi, wherein the mixture comprises Compound I:

Compound I of the present disclosure can be applied as Compound I or a formulation comprising Compound I by any of a variety of known techniques. For example, Compound I can be applied to the roots, stems, seeds, flowers or leaves of plants for the control of various fungi without damaging the commercial value of the plants. Compound I can also be applied as a foliar spray, soil spray, soil input, chemical solution irrigation, soil drench, soil injection or seed treatment. The substances may be applied in the form of any commonly used formulation type, for example, as a solution, dust, wettable powder, flowable concentrate, or emulsifiable concentrate.

Preferably, Compound I of the present disclosure is applied in the form of a formulation comprising Compound I together with a botanically acceptable carrier. Concentrated formulations can be dispersed in water or other liquids for application, or formulations can be in dust or granular form and then applied without further treatment. The formulation can be prepared according to procedures conventional in the field of agricultural chemistry.

The present disclosure contemplates all vehicles in which Compound I may be formulated for delivery and use as fungicides. Typically, the formulations are applied as aqueous suspensions or emulsions. Such suspensions or emulsions include solids commonly known as wettable powders; or from water-soluble, water-suspension, or emulsifiable formulations, which are liquids commonly known as emulsifiable concentrates, aqueous suspensions, or suspension concentrates. As can be readily appreciated, any substance to which Compound I can be added may be used provided that it does not significantly interfere with the activity of Compound I as an antifungal agent and produces the desired utility.

Wettable powders, which can be compressed to form water-dispersible granules, comprise an intimate mixture of Compound I, an inert carrier and a surfactant. The concentration of Compound I in the wettable powder may be from about 10% to about 90% by weight, more preferably from about 25% to about 75% by weight based on the total weight of the wettable powder. In the preparation of wettable powder formulations, Compound I may be used in combination with any finely divided solid such as propylite, talc, chalk, gypsum, Fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clay, diatomaceous earth, It can be compounded with purified silicates and the like. In this operation, finely divided carriers and surfactants are usually combined with Compound I and milled.

Emulsifiable concentrates of Compound I may contain, in a suitable liquid, an approximate concentration of Compound I, such as from about 10% to about 50% by weight, based on the total weight of the concentrate. Compound I can be dissolved in an inert carrier which is a mixture of a water-miscible solvent or a water-immiscible organic solvent and an emulsifier. The concentrate can be diluted with water and oil to form a spray mixture in the form of an oil-in-water emulsion. Useful organic solvents include aromatics, particularly the high-boiling naphthalene and olefinic portions of petroleum, such as heavy aromatic naphtha. Other organic solvents such as terpene solvents including rosin derivatives, aliphatic ketones such as cyclohexanone, and complex alcohols such as 2-ethoxyethanol may also be used.

Emulsifiers that can be advantageously used herein can be readily determined by one skilled in the art and include various nonionic, anionic, cationic and amphoteric emulsifiers, or combinations of two or more emulsifiers. Examples of nonionic emulsifiers useful for preparing 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 oxide, such as ethoxylated alkyl phenols and carboxylic esters solubilized with polyols or polyoxyalkylenes. Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include oil-soluble salts of alkylaryl sulfonic acids (eg, calcium), oil-soluble salts of sulfated polyglycol ethers, and suitable salts of phosphorylated polyglycol ethers.

Representative organic liquids that can be used to prepare emulsifiable concentrates of Compound I of the present invention include aromatic liquids such as xylenes, propyl benzene fractions; or substituted aromatic organic liquids such as mixed naphthalene fraction, mineral oil, dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, especially 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 may also be used to prepare emulsifiable concentrates. Organic liquids include xylene and propyl benzene fractions, with xylene being most preferred in some cases. Surface active dispersants are usually used in liquid formulations in an amount of 0.1 to 20% by weight based on the combined weight of compound I and dispersant. The formulations may also contain other compatible additives, such as plant growth regulators and other biologically active compounds used in agriculture.

Aqueous suspensions comprising 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 into a vehicle consisting of water and a surfactant selected from the same types as described above. Other ingredients, such as inorganic salts and synthetic or natural gums, may also be added to increase the density and viscosity of the aqueous vehicle.

Compound I can also be applied as a granular formulation which is particularly useful for soil application. Granular formulations generally contain from about 0.5 to about 10%, based on the total weight of the granular formulation, dispersed in an inert carrier consisting wholly or predominantly of coarsely divided inert materials, such as attapulgite, bentonite, diatomaceous earth, clay, or similar inexpensive materials. % by weight of compound I. Such formulations are usually prepared by dissolving Compound I in a suitable solvent and applying it to a pre-formed granular carrier to a suitable particle size ranging from about 0.5 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 preparing a dough or paste of the carrier and Compound I and solvent, milling and drying to obtain the desired granular particle size.

Dust containing Compound I can be prepared by intimately mixing Compound I in powdered form with a suitable dusty agricultural carrier such as kaolin clay, ground volcanic rock, and the like. The dust may contain from about 1 to about 10 weight percent of Compound I, based on the total weight of the dust.

The formulations may further contain auxiliary surfactants to enhance the deposition, wetting and penetration of Compound I onto target crops and organisms. These auxiliary surfactants may optionally be used as a component of a formulation or as a tank mixture. The amount of auxiliary surfactant will vary from 0.01 to 1.0% by volume, preferably from 0.05 to 0.5% by volume based on the spray-volume of water. Suitable auxiliary surfactants include ethoxylated nonylphenols, ethoxylated synthetic or natural alcohols, esters or salts of sulfosuccinic acid, ethoxylated organosilicones, ethoxylated fatty amines, or combinations of surfactants with mineral or vegetable oils. However, it is not limited thereto. The formulation may also include an oil-in-water emulsion as disclosed in US Patent Application Serial No. 11/495,228, the disclosure of which is incorporated herein by reference.

In certain instances, formulations of Compound I may be advantageously nebulized via aerial application using an aircraft or helicopter. The exact composition of these aerial applications depends on the crop being treated. Aerial applications for vegetables are standard surfactants, wetting, tacky, diffusing or penetrating additives such as non-ionic surfactants, organosilicon, preferably 0.05 to 15%, preferably based on the spray volume of water. , or spray volumes of 15 to 50 L/ha with crop oil concentrates.

Formulations may optionally include combinations containing other pesticide compounds. Such additional pesticide compounds are compatible with fungicides, insecticides, herbicides, nematocides, acaricides, arthropods, bactericides, compounds of the present invention in the medium selected for application and are active of the present compounds. additives, such as non-ionic surfactants, organosilicones, or crop oil concentrates, or combinations thereof. Thus, in these embodiments, other pesticide compounds are used as supplemental toxicants for the same or different pesticide applications. Compound I and the pesticide compound in the combination may generally be present in a weight ratio of 1:100 to 100:1.

Compound I of the present disclosure can also be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof. Compound I of the present disclosure is often applied in combination with one or more other fungicides to control a wider variety of undesirable diseases. When used in conjunction with other fungicide(s), Compound I as claimed herein may be formulated with the other fungicide(s), tank-mixed with the other fungicide(s), or applied sequentially with the other fungicide(s). can Other such fungicides include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, amethoxtradine, amisulbromine, antimycin, Amphelomyces quiscu Alis ( Ampelomyces quisqualis ), azaconazole, azoxystrobin, Bacillus subtilis ( Bacillus subtilis ), Bacillus subtilis ( Bacillus subtilis ) strain QST713, benalaxyl, benomyl, benthiavalicarb-isopropyl, benzylamino Benzene-sulfonate (BABS) salt, bicarbonate, biphenyl, bismerthiazole, bitertanol, bixafen, blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole, buprimate, calcium Polysulfide, captafol, captan, carbendazim, carboxin, carpropamide, carvone, clazaphenone, chloroneb, chlorothalonil, clozolinate, Coniothyrium minitans , copper hydroxide , copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide, cyazopamide, cyflufenamide, simoxanil, ciproconazole, ciprodinil, dazomet, debacarb, diammonium Ethylenebis-(dithiocarbamate), dichlorofluanid, dichlorophen, diclosymet, diclomezine, dicloran, diethofencarb, diphenoconazole, difenzoquat ion, diflume torim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine, dodine free base, eddy Fenfos, Enestrobin, Enestroburine, Epoxyconazole, Ethaboxam, Ethoxyquin, Etridiazole, Famoxadone, Fenamidone, Fenarimol, Fenbuconazole, Fenfuram, Fenhexamid, Fenoxa nil, fenpiclonil, fenpropidine, fenpropimorph, fenpyrazamine, fentin, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph, flu opicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flucilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapiroxad, folfet, form Aldehyde, fosetyl, fosetyl-aluminum, puberidazole, furalaxyl, furamepyr, guazatine, guazatin acetate, GY-81, hexachlorobenzene, hexaconazole, hymexazole, imazalil, imazalil Sulfate, Imibenconazole, Iminoctadine, Iminoctadine Triacetate, Iminoctadine Tris (Albesilate), Iodocarb, Ifconazole, Iiffenpyrazolone, Iprobenfos, Iprodione, Ipro Balicarb, isoprothiolane, isopyrazam, isotianil, kasugamycin, kasugamycin hydrochloride hydrate, cresoxim-methyl, laminarin, mancopher, mancozeb, mandipropamide, maneb, Mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercuric chloride, mercuric oxide, mercuric chloride, metalaxyl, metalaxyl-M, metam, metam-ammonium, metam-potassium, metam- sodium, metconazole, metasulfocarb, methyl iodide, methyl isothiocyanate, metiram, methominostrobin, metrafenone, mildiomycin, miclobutanil, nabam, nitrothal-isopropyl , Nuarimol, Octylinone, Ofurace, Oleic Acid (Fatty Acid), Orysastrobin, Oxadixyl, Auxine-Copper, Oxfoconazole Fumarate, Oxycarboxin, Fefurazoate, Fenconazole, Pensicurone, Fenflufen, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercuric acetate, phosphonic acid, phthalide, picoxystrobin, polyoxin B, polyoxin, polyoxolim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazide, prothioconazole, pyraclostrobin, blood Rametostrobin, Pyraoxystrobin, Pyrazophos, Pyribencarb, Pyributicarb, Pyrifenox, Pyrimethanil, Pyriophenone, Pyroquilon, Quinoclamine, Quinoxifen, Quintogen, Ray Reynoutria sachalinensis extract, sedakic acid, silthiofam, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, tar oil , tebuconazole, tebufloquine, tecnazen, tetraconazole, thiabendazole, tifluzamide, thiophanate-methyl, thiram, thiadinyl, tolclofos-methyl, tolylfluanid, triadi Mepon, Triadimenol, Triazoxide, Tricyclazole, Tridemorph, Trifloxystrobin, Triflumizole, Tripoline, Triphenyltin Hydroxide, Triticonazole, Validamycin, Valifenalate, Vali Phenal, Vinclzoline, Zineb, Ziram, Zoxamide, Candida oleophila, Fusarium oxysporum, Gliocladium species, Phlebiopsis gigantea ), Streptomyces griseoviridis ( Streptomyces griseoviridis ), Trichoderma species, ( 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-hepta Decyl-2-imidazolin-1-yl)ethanol, 2,3-dihydro-5-phenyl-1,4-dithy-in 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 thiocyanate tem , aminopyrifene, ampropylphos, anilazine, azitiram, barium polysulfide, Bayer 32394, benodanil, benquinox, bentaluron, benzamacryl; Benjamacryl-isobutyl, benzamorph, benzovindiflupyr, binapacryl, bis(methylmercury) sulfate, bis(tributyltin) oxide, butiobate, cadmium calcium copper zinc chromate sulfate, char Vamorph, CECA, cloventiazone, chloraniformethane, chlorphenazole, chlorquinox, climbazole, copper bis(3-phenylsalicylate), copper zinc chromate, coumoxystrobin, cupraneb , cupric hydrazinium sulfate, cuprobam, cyclapuramide, cypendazole, cipropuram, decafentine, diclobentiazox, diclon, diclozoline, diclobutrazole, dimethylrimole, Dinoctone, Dinosulfone, Dinoterbone, Dipimethytron, Dipyrithione, Ditalymphos, Dodicin, Drazoxolone, EBP, Enoxastrobin, ESBP, Etaconazole, Etem, Etirim, Phenaminosulf , phenaminestrobin, phenafanil, phenitrophan, fenpicosamide, fluidafil, fluopimomid, fluotrimazole, fluphenoxystrobin, furcarbanil, furconazole, furconazole-cis, purume Cyclox, Furophanate, Gliodin, Griseofulvin, Halacrine, Hercules 3944, Hexylthiophos, ICIA0858, Influxam, Ipfentrifluconazole, Ipflufenoquin, Isopetamide, Isoflusif Ram, Isofamphos, Isovaledione, Mandestrobin, Mebenil, Mecarbingide, Mefentrifluconazole, Metazoxolone, Metfuroxam, Methylmercuric Dicyandiamide, Metsulfovax, Methyltetraprole, Milneb, Mucochloric anhydride, miclozoline, N -3,5-dichlorophenyl-succinimide, N -3-nitrophenylitaconimide, natamycin, N -ethylmercurio-4-toluenesulfoanilide, nickel bis( dimethyldithiocarbamate), OCH, oxathiapiproline, phenylmercury dimethyldithiocarbamate, phenylmercury nitrate, phosdiphene, picabutrazox, prothiocarb; Prothiocarb hydrochloride, pidiflumetofen, piracarbolide, pirapropoin, pirajiflumid, pyridaclomethyl, pyridinitrile, pyrisoxazole, pyroxychlor, piroxypur, quinacetol, Quinacetol sulfate, quinazamide, quinconazole, quinopmelin, labenzazole, salicylanilide, SSF-109, sultropen, tecoram, thiadifluor, tisiophen, thiochlorfenfim, thiophanate, thioquinox, thioximide, triamiphos, triarimol, triazbutyl, triclamide, triclopycarb, triflumezopyrim, urbaside, xarylamide, and any combination thereof. can

In addition, compound I of the present invention is compatible with the compound of the present invention in the medium selected for application and is not antagonistic to the activity of compound I as an insecticide, nematicide, acaricide, acaricide, acaricide It may be combined with other pesticides, including bacterial agents or combinations thereof, to form pesticide mixtures and synergistic mixtures thereof. Compound I of the present disclosure can be applied in combination with one or more other pesticides to control a wider variety of undesirable pests. When used in conjunction with other pesticides, Compound I as claimed herein may be formulated with the other pesticide(s), tank-mixed with the other pesticide(s), or applied sequentially with the other pesticide(s). Common insecticides include, but are not limited to: antibiotic insecticides such as allosamidine and thuringiensine; macrocyclic lactone insecticides such as spinosad and spinetoram; abamectin insecticides such as abamectin, doramectin, emamectin, eprinomectin, ivermectin and selamectin; milbemycin insecticides such as lepimectin, milbemectin, milbemycin oxime and moxidectin; carbamate insecticides such as bendicarb and carbaril; benzofuranyl methylcarbamate insecticides such as benfuracarb, carbofuran, carbosulfan, decarbofuran and furatiocarb; dimethylcarbamate insecticides dimitan, dimethylane, hyquincarb and pyrimicarb; Oxime carbamate insecticides such as alanicarb, aldicarb, aldoxycarb, butocarboxime, butoxycarboxim, methomyl, nitrilacarb, oxamil, tazimcarb, thiocarboxime, thiodicarb and thiophanox; Phenyl methylcarbamate insecticides such as alixicarb, aminocarb, bufencarb, butacarb, carbanolate, chlorotocarb, dicresyl, dioxacarb, EMPC, ethiophencarb , penetacarb, phenobucarb, isoprocarb, methiocarb, metolcarb, mexacarbate, promasil, promecarb, propoxur, trimetacarb, XMC and xylylcarb ; desiccant insecticides such as boric acid, diatomaceous earth and silica gel; Diamide insecticides such as broflanilide, chlorantraniliprole, cyanthraniliprole, cyclaniliprole, cyhalodiamide, flubendiamide, tetrachlorantraniliprole, and tetranil leaf roll; diarylisoxazoline insecticides such as fluxamethamide; dinitrophenol insecticides such as Dinex, Dinoprop, Dinosam and DNOC; fluorine insecticides such as barium hexafluorosilicate, cryolite, sodium fluoride, sodium hexafluorosilicate and sulfuramide; formamidine insecticides such as amitraz, chlordimeform, formethanate and formparanate; Fumigants 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, mercury chloride, potassium thiocyanate and sodium thiocyanate; Chitin synthesis inhibitors such as bistrifluron, buprofezin, chlorfluazuron, cyromazine, diflubenzuron, flucyclozuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, nobiflumuron, fenflu ron, teflubenzuron and triflumuron; juvenile hormone mimics such as epofenonane, phenoxycarb, hydroprene, kinoprene, 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; shedding inhibitors such as diophenolane; precocenes such as precocene I, precocene II and precocene III; unclassified insect growth regulators such as dicyclanil; Nereistoxin-like insecticides such as bensultap, cartap, thiocyclam and thiosultap; pyridylpyrazole insecticides such as ticlopyrazoflor; nicotinoid insecticides such as flunicamide; nitroguanidine insecticides such as clothianidin, dinotefuran, imidacloprid and thiamethoxam; nitromethylene insecticides such as nitenpyram and nithiazine; pyridylmethyl-amine insecticides such as acetamiprid, cycloxaprid, imidacloprid, nitenpyram and thiacloprid; organochlorine insecticides such as bromo-DDT, campeflor, DDT, pp'-DDT, ethyl-DDD, HCH, gamma-HCH, lindane, methoxychlor, pentachlorophenol and TDE; Cyclodiene insecticides such as aldrin, bromocyclen, chlorbicyclen, chlordane, chlorodecone, dieldrin, dilor, endosulfan, alpha-endosulfan, endrin, HEOD, heptachlor, HHDN, isobenzene, Isodrine, Kelevan and Mirex; Organophosphate insecticides such as bromfenvinphos, chlorfenvinphos, crotoxyphos, dichlorvos, dicrotophos, dimethylvinphos, phospyrates, heptenophos, metocrotophos, mebinphos, monocrotophos, nalled, naphthalophos, phosphamidon, propafos, TEPP and tetrachlorvinphos; organothiophosphoric acid insecticides such as dioxabenzophos, fosmethylane and pentoate; Aliphatic organothiophosphate insecticides such as acethion, amitone, cadusaphos, chlorethoxyphos, chlormephos, demepion, demepion-O, demepion-S, demetone, demeton-O , demeton-S, demeton-methyl, demeton-O-methyl, demeton-S-methyl, demeton-S-methylsulfone, disulfotone, ethione, etoprophos, IPSP, isothioate, mala thione, methacryphos, oxydemeton-methyl, oxydeprophos, oxydisulfotone, phorate, sulfothep, terbufos and thiometone; aliphatic amide organothiophosphate insecticides such as amidithione, cyanthoate, dimethoate, ethoate-methyl, formothion, mecarbam, omethoate, protoate, sofamid and bamidothion; oxime organothiophosphate insecticides such as chlorphoxim, phoxim and phoxim-methyl; Heterocyclic organothiophosphate insecticides such as azametifos, coumaphos, coumitoate, dioxathion, endothione, menazone, morphothione, fosalone, pyraclopos, pyridapenthione and quinothione ; benzothiopyran organothiophosphate insecticides such as diticrofos and ticrofos; benzotriazine organothiophosphate insecticides such as azinphos-ethyl and azinphos-methyl; isoindole organothiophosphate insecticides such as diallipos and fosmet; isoxazole organothiophosphate insecticides such as isoxathion and zolapropos; pyrazolopyrimidine organothiophosphate insecticides such as chlorprazophos and pyrazophos; pyridine organothiophosphate insecticides such as chlorpyrifos and chlorpyrifos-methyl; pyrimidine organothiophosphate insecticides such as butathiophos, diazinon, etrimphos, lirimphos, pyrimiphos-ethyl, pyrimiphos-methyl, primidophos, pyrimitate and tebupirimphos; quinoxaline organothiophosphate insecticides such as quinalphos and quinalphos-methyl; thiadiazole organothiophosphate insecticides such as atidathione, lithathione, methidathione and protidathione; triazole organothiophosphate insecticides such as isazophos and triazophos; Phenyl organothiophosphate insecticides such as azotoate, bromophos, bromophos-ethyl, carbafenothione, chlorthiophos, cyanophos, cythioate, dicaptone, diclofenthion, etaphos, Famphur, fenchlorphos, fenitrothion, phensulfothion, fenthion, fenthion-ethyl, heterophos, jodfenphos, mesulfenphos, parathion, parathion-methyl, phencaptone, fosnichlor, propenophos , prothiophos, sulprophos, temephos, trichlormetaphos-3 and tryphenophos; phosphonic acid insecticides such as butonate and trichlorphone; phosphonothionic acid insecticides such as mecarfone; phenyl ethylphosphonothionic acid insecticides such as phonofos and trichloronath; phenyl phenylphosphonothionic acid insecticides such as cyanophenphos, EPN and leptophos; phosphoaminate insecticides such as croformate, phenamiphos, fostiethane, mephosfolian, phospholan and pyrimetaphos; phosphoamidothionic acid insecticides such as acephate, isocarbophos, isofenphos, isopenphos-methyl, metaamidophos and propetamphos; phosphorodiamide insecticides such as dimepox, majidox, mipafox and shiradan; oxadiazine insecticides such as indoxacarb; oxadiazoline insecticides such as methoxadiazone; phthalimide insecticides such as diallipos, phosmet and tetramethrin; pyrazole insecticides such as tebufenpyrad, tolefenpyrad; phenylpyrazole insecticides such as acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole and vaniliprole; Pyrethroid ester insecticides such as acrinathrin, allethrin, bioallethrin, barthrin, bifenthrin, kappa-bifenthrin, bioethanomethrin, chloropralethrin, cycloethrin, cycloprothrin, Cyfluthrin, beta-cypermethrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cy Permethrin Cyphenothrine, Deltamethrin, Dimefluthrin, Dimethrin, Amfenthrin, Fenfluthrin, Fenpyrithrin, Fenpropatrine, Fenvalerate, Espenvalerate, Flucitrinate, Fluvali nate, tau-fluvalinate, purethrin, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, epsilon-methoflutrin, mofluorothrin, epsilon-momfluorothrin, permethrin, Biopermethrin, transfermethrin, phenothrine, pralethrin, profluthrin, pyresmethrin, resmethrin, bioresmethrin, cismetrin, tefluthrin, kappa-tefluthrin, teralethrin, tetra methrin, tetramethylfluthrin, tralomethrin and transfluthrin; pyrethroid ether insecticides such as Etofenprox, Flufenprox, Halfenprox, Protrifenbut and Silafluofen; pyrimidineamine insecticides such as flufenerim and pyrimidifen; pyrrole insecticides such as chlorfenapyr; tetramic acid insecticides such as spiropidione and spirotetramat; tetronic acid insecticides such as spiromesifen; thiourea insecticides such as diafenthiuron; urea insecticides such as flucofuron and sulcofuron; unclassified nematicides such as fluazaindolizine and thioxazafen; and unclassified insecticides such as benpyrimoxane, closantel, copper naphthenate, crotamiton, EXD, fenazaflor, fenoxacrim, fluhexaphone, flupyrimine, hydramethylnon, isoprothiolane, malonovene , metaflumizone, nifluridide, oxazolesulfil, plefenate, pyridaben, pyridalyl, pyrifluquinazone, rafoxanide, sulfoxaflor, triaraten and triazamate, and any combination thereof includes

Additionally, Compound I of the present invention is compatible with the compound of the present invention in the medium selected for application and can be combined with herbicides that are not antagonistic to the activity of Compound I to form pesticide mixtures and synergistic mixtures thereof. The fungicidal compounds I of the present disclosure can be applied in combination with one or more herbicides to control a wider variety of undesirable plants. When used in conjunction with a herbicide, 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). Common herbicides include, but are not limited to: amide herbicides such as alidochlor, beflubutamide, benzadox, benzipram, bromobutide, carpenstrol, CDEA, ciprazole, dimethenamide, di Methenamide-P, dipentamide, epronaz, etnipromid, fentrazamide, flupoxam, fomesafen, halosafen, isocarbamide, isoxaben, napropamide, naptalam, fetoxamide , propizamide, quinonamide, tebutam and thiafenacil; Anilide herbicides such as chloranocril, cisanilide, clomeprop, cypromid, diflufenican, etobenzanid, fenasulam, flufenacet, flufenican, mefenacet, mefluidide, metamifop, monalide, naproanilide, pentanochlor, picolinafen and propanil; arylalanine herbicides such as Benzoylprop, Flamprop and Flamprop-M; Chloroacetanilide herbicides such as acetochlor, alachlor, butachlor, butenachlor, delachlor, dietathyl, dimethachlor, metazachlor, metolachlor, S-metolachlor, pretilachlor, propachlor, propisochlor, prinachlor, tebuchlor, tenylchlor and xylachlor; sulfonanilide herbicides such as benzofluor, perfluidone, pyrimisulfan and profluazole; sulfonamide herbicides such as asulam, carbasulam, penasulam and oryzalin; thioamide herbicides such as chlorthiamid; antibiotic herbicides such as vilanafos; benzoic acid herbicides such as chloramben, dicamba, 2,3,6-TBA and tricamba; pyrimidinyloxybenzoic acid herbicides such as bispyribac and pyriminobac; pyrimidinylthiobenzoic acid herbicides such as pyrithiobac; phthalic acid herbicides such as chlorthal; picolinic acid herbicides such as aminopyralid, clopyralid, flopyrauxifen, halauxifen, and picloram; quinolinecarboxylic acid herbicides 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 fenquinotrione, lancotrione, mesotrione, sulcotrione, tefuryltrione and tembotrione; benzofuranyl alkylsulfonate herbicides such as benfuresate and etofumesate; benzothiazole herbicides such as benzazolines; carbamate herbicides such as asulam, carboxazole chlorprocarb, dichlormate, penasulam, carbutyrate and terbucarb; Carvanylate herbicides such as barban, BCPC, carbasulam, carbetamide, CEPC, chlorbufam, chlorpropham, CPPC, decimedipham, penisopharm, penmedipharm, penmedipham-ethyl, propham and sweb ; cyclohexene oxime herbicides such as alloxydim, butoxydim, clethodim, cloproxydim, cycloxydim, propoxydim, setoxydim, tepraloxydim and tralkoxydim; cyclopropyllisoxazole herbicides such as isoxachlortol and isoxaflutol; dicarboximide herbicides such as cinidon-ethyl, flumezin, flumiclorac, flumioxazine and flumipropine; Dinitroaniline herbicides such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, isopropalin, metalpropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin and triple luralin; dinitrophenol herbicides such as dinophenate, dinoprop, dinosam, dinoceb, dinoteb, DNOC, ethinophen and medinoterb; diphenyl ether herbicides such as ethoxyphene; Nitrophenyl ether herbicides such as acidoflurfen, aclonifen, bifenox, clomethoxyfen, chlornitrofen, etnipromid, fluorodifen, fluoroglycopene, fluoronitrofen, formesafen, furyloxy pen, halosaphene, lactofen, nitrophene, nitrofluorphene and oxyfluorphene; dithiocarbamate herbicides such as dazomet and metam; halogenated aliphatic herbicides such as allolac, chloropon, dalapon, flupropanate, hexachloroacetone, iodomethane, methyl bromide, monochloroacetic acid, SMA and TCA; imidazolinone herbicides such as imazamethabenz, imazamox, imazapic, imazapir, imazaquin and imazetapyr; inorganic herbicides such as ammonium sulfamate, borax, calcium chlorate, copper sulfate, iron sulfate, potassium azide, potassium cyanide, sodium azide, sodium chlorate and sulfuric acid; nitrile herbicides such as bromobonil, bromoxynil, chloroxynil, cyclopyranil, diclobenil, iodobonil, ioxinil and pyraclonil; Organophosphorus herbicides such as amiprofos-methyl, anilofos, bensulide, bilanafos, butamifos, 2,4-DEP, DMPA, EBEP, fosamine, glufosinate, glufosinate-P, glypho sate and piperophos; phenoxy herbicides such as bromofenoxime, clomeprop, 2,4-DEB, 2,4-DEP, diphenopenten, disul, erbon, etnipromid, penteracol and triphoxime; oxadiazoline herbicides such as methazole, oxadiargyl, oxadiazone; oxazole herbicides such as phenoxasulfone; phenoxyacetic acid herbicides such as 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl and 2,4,5-T; phenoxybutyric acid herbicides such as 4-CPB, 2,4-DB, 3,4-DB, MCPB and 2,4,5-TB; phenoxypropionic acid herbicides such as cloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop and mecoprop-P; Aryloxyphenoxypropionic acid herbicides such as chlorazifop, clodinafop, clofop, chalofop, diclofop, fenoxaprop, fenoxaprop-P, pentiaprop, fluazifop, fluazifop -P, haloxyfop, haloxyfop-P, isoxapirifop, metaamifop, propaquizafop, quizalofop, quizalofop-P and tripop; phenylenediamine herbicides such as dinitramine and prodiamine; pyrazole herbicides such as pyroxasulfone; benzoylpyrazole herbicides such as benzofenaf, pyrasulfotole, pyrazolinate, pyrazoxifen, tolpyralate, and topramezone; phenylpyrazole herbicides such as fluazolate, nipyraclofen, pioxaden and pyraflufen; pyridazine herbicides such as credazine, cyclopyrimolate, pyridafol and pyridate; pyridazinone herbicides such as brompyrazone, chloridazone, dimidazone, flufenpyr, metflurazone, norflurazone, oxapirazone and pidanone; Pyridine herbicides such as aminopyralid, cliodinate, clopyralid, dithiopyr, florpyrauxifene, fluroxypyr, halauxifen, haloxydine, picloram, picolinafen, pyrchlor, thia zopyr and triclopyr; pyrimidinediamine herbicides such as iprimidam and thiochlorim; quaternary ammonium herbicides such as cyperquat, dietamquat, difenzoquat, diquat, morphamquat and paraquat; Thiocarbamate herbicides such as butyrate, cycloate, di-alate, EPTC, esprocarb, ethiolate, isopolynate, methiobencarb, molinate, orbencarb, febulate, pro sulfocarb, pyributicarb, sulfalate, thiobencarb, thiocarbazil, tri-alate and vernolate; thiocarbonate herbicides such as dimexano, EXD and proxane; thiourea herbicides such as methiuron; triazine herbicides such as dipropetrin, indaziflam, triaziflam and trihydroxytriazine; Chlorotriazine herbicides such as atrazine, chlorazine, cyanazine, ciprazine, eglinazine, ipazine, mesoprazine, procyazine, proglinazine, proparzine, cebutylazine, simrazine, terbutylazine and tri etaazine; methoxytriazine herbicides such as atratone, metometon, prometon, secbumeton, symeton and terbumeton; methylthiotriazine herbicides such as amethrin, aziprothrin, cyanathrin, desmetrin, dimetamathrin, metoprothrin, promethrin, cimetrin and terbutrin; triazinone herbicides such as ametridione, amibuzin, hexazinone, isomethiozine, metamitron, metribuzin, and trifludimoxin; triazole herbicides such as amitrol, carpenstrol, epranaz and flupoxam triazolone herbicides such as amicarbazone, bencarbazone, carfentrazone, flucarbazone, ipfencarbazone, propoxycarbazone, sulfentrazone and thiencarbazone-methyl; triazolopyrimidine herbicides such as cloransulam, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam and pyroxsulam; uracil herbicides such as benzfendizone, bromacil, butafenacil, flupropacil, isocil, lenacil, saflufenacil, thiafenacil, and terbacil; urea herbicides such as benzthiazuron, cumyluron, cycloron, dichloralurea, diflufenzopyr, isonoruron, isouron, metabenzthiazuron, monisouron and noruron; Phenylurea herbicides such as anisuron, buturon, chlorbromuron, chloreturon, chlorotoluron, chloroxuron, dimuron, diphenoxuron, dimepuron, diuron, phenururon, fluomethuron, Fluorothiuron, isoprothuron, linuron, methyuron, methyldymron, methobenzuron, methobromuron, methoxuron, monolinuron, monuron, neburon, parafluuron, phenobenzuron, sidu uron, tetraphlon and tidiazuron; Pyrimidinesulfonylurea herbicides such as amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, cyclosulfamuron, ethoxysulfuron, plazasulfuron, flucetosulfuron, flupyrsulfuron, forramsulfuron, halosulon Furon, imazosulfuron, mesosulfuron, metazosulfuron, nicosulfuron, orthosulfuron, oxasulfuron, premisulfuron, propyrisulfuron, pyrazosulfuron, rimsulfuron, sulfomethuron, sulfosulfuron and triprooxysulfuron; Triazinylsulfonylurea herbicides such as chlorosulfuron, cinosulfuron, ethanemethsulfuron, iodosulfuron, iophensulfuron, metsulfuron, prosulfuron, thifensulfuron, triasulfuron, tribenuron, triflusulon furon and tritosulfuron; thiadiazolylurea herbicides such as buthiuron, ethidimuron, tebuthiuron, thiazafluron and tidiazuron; and unclassified herbicides such as acrolein, allyl alcohol, aminocyclopyrachlor, azafenidine, bentazone, benzobicyclone, bicyclopyrone, butidazole, calcium cyanomid, cambendichlor, chlorfenac, chlorfenprop, Chlorflurazole, Chlorfluenol, Cinmethylin, Clomazone, CPMF, Cresol, Cyanamide, Cyclopyrimorate, Ortho -Dichlorobenzene, Dimepiperate, Endothal, Fluoromidine, Fluridone , flurochloridone, flutamone, fluthiacet, indanophan, methyl isothiocyanate, OCH, oxaziclomefone, pentachlorophenol, pentoxazone, phenylmercury acetate, prosulfaline, pyribenzoxime, pyrip thalide, quinocylamine, rodetanil, sulglycapine, thidiazimine, tridiphane, trimeturon, triprofindan and tritac.

Compounds I of the present invention may also contain or be applied concurrently and/or sequentially with further active compounds. These additional compounds may be plant health stimulants, such as organic compounds, inorganic fertilizers, or micronutrient donors or other preparations that affect plant growth, such as inoculum.

In another embodiment, Compound I may also include or be applied together with and/or sequentially with other biological organisms, such as Bacillus strains, such as Bacillus subtilis strains. Amyloiquefaciens FZB24 ( ^TAEGRP® ) and Bacillus amyloiquefaciens FZB42 ( ^RHIZOVITAL® ), VotiVo™ Bacillus firmus, Clariva™ (Pasteuria nishizawae) ), Bacillus thuringiensis, Trichoderma species, and/or mutants and metabolites of each strain exhibiting activity against insects, mites, nematodes and/or plant pathogens, but hereby Not limited.

One embodiment of the present disclosure is a method for controlling or preventing fungal attack. This method involves the application of a fungicidally effective amount of formula I to soil, plants, roots, leaves, seeds or loci of fungi, or to loci in which infestation is to be prevented (e.g. to cereal or grape plants). include Compound I, while exhibiting low phytotoxicity, is suitable for the treatment of various plants at the level of fungicides. Compound I may be useful in both a protective and/or exterminator mode.

The compounds of formula I have been found to have a significant fungicidal effect, especially for agricultural use. The compounds of formula I are particularly effective for use with agricultural crops and horticultural plants. Additional benefits may include, but are not limited to: improving plant health; improving the yield of plants (eg increased biomass and/or increased content of valuable components); improving plant vigor (eg improved plant growth and/or greener leaves); improving the quality of plants (eg improved content or composition of certain ingredients); and improving the tolerance of plants to abiotic and/or biotic stresses.

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

Above cucurbits: powdery mildew ( Erysiphe cichoracearum , Sphaerotheca fuliginea ), ring spot ( Mycosphaerella brassicicola ), blackleg ( 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. ), Fusarium wilt ( Fusarium oxysporum ), belly rot ( Rhizoctonia solani ), Corynespora blight / target spot ( 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 );

On tomatoes: powdery mildew ( Leveillula taurica ), Septoria leaf spot ( Septoria lycopersici ), white mold ( Sclerotinia sclerotiorum, Sclerotinia minor ), target spot ( Corynespora cassiicola ), southern blight ( Sclerotium rolfsii ), gray mold ( Botrytis cinerea ), gray leaf spot ( Stemphylium spp.), Fusarium blight, Fusarium tree and root rot ( Fusarium wilt, Fusarium crown and root rot) ( Fusarium oxysporum ), anthrax ( Colletotrichum coccodes, Colletotrichum dematium, Colletotrichum gloeosporioides, Glomerella cingulate ), Alternaria stem canker and black mold ( Alternaria alternata ), Black root rot ( Chalara elegans ), Cercospora leaf mold ( Cercospora fuligena ), charcoal rot ( Macrophomina phaseolina ), corky root rot ( Pyrenochaeta lycopersici ), Didymella stem rot ( Didymella lycopersici ), early blight ( Alternaria solani ), leaf mold ( Passalora fulva, Mycovellosiella fulva ), poma rot ( Phoma destructiva ), and sour rot ( Geotrichum candidum );

On leafy vegetables: Cercospora leaf mold ( Cercospora longissimi , Cercospora spp. ), gray mold/Botrytis rot ( Botrytis cinerea ), Alternaria leaf spot and blight ( 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. ), southern blight ( Sclerotium rolfsii ), basal rot ( Phoma exigua ), Rhizoctonia bottom rot ( Rhizoctonia solani ), Sclerotinia scleroderma (Sclerotinia drop) ( Sclerotinia minor , Sclerotinia sclerotiorum ), and Stemphylium leaf spot ( Stemphylium botryosum );

On potatoes: anthracnose or black dot ( Colletotrichum coccodes ), brown spot and black pit ( Alternaria alternata ), Cercospora leaf blotch ( Cercospora concors ), charcoal Charcoal rot ( Macrophomina phaseolina ), common rust ( Puccinia pittieriana ), deforming rust ( Aecidium cantensis ), early blight ( Alternaria solani ), Fusarium dry rot and Fusarium Fusarium dry rot and Fusarium wilt ( Fusarium spp. ), gangrene ( Phoma exigua f. sp. foveata ), gray mold ( Botrytis cinerea ), black blight or poma leaf spot or Phoma leaf spot) ( Stagonosporopsis andigena , Phoma andigena var. andinai ), powdery mildew ( Erysiphe cichoracearum ), Rhizoctonia canker and black scurf ( Rhizoctonia solani ), Rosellinia black rot (Rosellinia black rot) ( Roselliniaspp .), Septoria leaf spot ( Septoria lycopersici var. malagutil ), silver scurf ( Helminthosporium solani ), skin spot ( Polyscytalum pustulans ), vein rot ( stem rot) ( Sclerotium rolfsii ), Thecaphora smut ( Thecaphora solani ), Ulocladium blight ( Ulocladium atrum ), Verticillium wilt ( Verticillium albo-atrum ) , and white mold ( Sclerotinia sclerotiorum );

On peppers: southern blight ( Sclerotium rolfsii ), powdery mildew ( Leveillula taurica ), anthracnose ( Colletotrichum capsici , Colletorichum acutatum , Colletorichum spp. ), Cercospora (frogeye) leaf spot ( Cercospora capsici , Cercospora spp. ), charcoal rot ( Macrophomina phaseolina ), damping-off and root rot ( Rhizoctonia solani ), Fusarium stem rot ( Fusarium solani ) , Fusarium wilt ( Fusarium oxysporum f. sp. capsici ), gray leaf spot ( Stemphylium spp. ), gray mold ( gray mold) ( Botrytis cinerea ), verticillium foot blight ( Verticillium wilt ( Verticillium albo-atrum ), and white mold ( Sclerotinia sclerotiorum );

On cole crops: Alternaria leaf spot and blight ( Alternaria brassicicola, Alternaria spp. ), anthracnose ( Colletotrichum spp. ), black leg ( Leptosphaeria maculans , Phoma lingam ), Cercospora leaf spot ( Cercopsora spp. ), Fusarium yellows and other diseases (Fusarium spp. ), Gray mold/Botrytis blight ( Botrytis cinerea ), Powdery mildew ( Erysiphe polygoni ), Rhizoctonia rot and blight ( Rhizoctonia solani ), ring spot ( Mycosphaerella brassicicola ), Sclerotinia rot ( Sclerotinia spp. ), white leaf spot ( Pseudocercosporella capsellae ).

Compound I was found to have a significant fungicidal effect against phytopathogenic fungi of agriculturally useful vegetable crops. These diseases include Alternaria brassicicola , which causes black leaf spot on cabbage; Alternaria brassicicola , which causes tomato early blight; Sclerotinia sclerotiorum, which causes Sclerotinia rot of lettuce; Colletotrichum capsici , which causes pepper anthrax; Erysiphe cichoracearum, which causes cucumber powdery mildew; Mycobellosiella fulva , which causes leaf mold on tomatoes; Stagonosporopsis cucurbitacearum, which causes watermelon vine blight; and Botrytis cinerea , which causes broad bean gray mold, especially for agricultural use. Compound I is particularly effective for use with agricultural crops and horticultural plants.

Compound I has broad efficacy as a fungicide. The exact amount of active substance to be applied depends not only on the particular active substance applied, but also on the particular measures desired, the fungal species to be controlled, and their stage of growth, as well as the part of the plant or other product that will come into contact with the compound. Thus, Compound I, and formulations containing it, may not be equally effective at similar concentrations or against the same fungal species.

Compound I is effective in inhibiting disease and for use in plants in botanically acceptable amounts. The term "disease inhibiting and botanically acceptable amount" refers to an amount of a compound that kills or inhibits the plant disease for which control is desired, but is not significantly toxic to the plant. This amount is generally from about 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm being preferred. The exact concentration of compound required depends on the fungal disease to be controlled, the type of formulation used, the method of application, the particular plant species, climatic conditions, and the like. A suitable application rate is typically about 0.10 to about 4 pounds per acre (about 0.01 to 0.45 grams per square meter, g/m ² ).

As will be apparent to those skilled in the art for understanding the teachings herein, any range or desired value given herein may be extended or changed without losing the effect sought.

yes:

Field assessment of Alternaria brassicicola (ALTEBI) on cabbage:

Cabbage plants (BRSOL) were head sprayed three times with a fungicide treatment containing Compound I applied in a 5% EC formulation and tank-mixed with an adjuvant (Trycol, 0.2% v/v to 50% w/w), cabbage was applied once in the 10-12 LF step of The following applications were carried out at 7-day intervals, and all applications were sprayed at rates of 50, 100 and 150 active ingredients per hectare (g ai/ha). Two days after the single application, the experimental plots were inoculated with the black leaf spot pathogen. The treatment was part of an experimental trial designed as a random complete block with 4 replicates and a plot of approximately 2 x 1 m, Compound I was applied at a water volume of 800 L/ha.

Disease severity was assessed as the percentage of diseased areas of cabbage bottom leaves (6 plants per plot at random). Gross infection was assessed in triplicate during testing on day 7 after each application. The area under the translational progression curve (AUDPC) was calculated for each plot using the recorded severity data set. Relative AUDPC (% control based on AUDPC) was calculated as percent of untreated control. Results are given in Table 1.

Field evaluation of Sclerotinia sclerotiorum (SCLESC) on lettuce:

A fungicide treatment containing a 5% EC formulation of compound I plus an adjuvant (Trycol, 50% w/w at 0.2% v/v) was head sprayed to lettuce plants (LACSC) twice, with one application At the heading stage after 36 days of planting, the second application was after 7 days. Formulations of Compound I were applied at active ingredient rates of 50, 100 and 150 grams per hectare (g ai/ha). Experimental plots were inoculated with Sclerotinia rot pathogens 2 days after one application. The treatment was part of an experimental trial designed as a random complete block with 4 replicates and a plot of approximately 2 x 1 m, and the formulation of Compound I was applied in a water volume of 800 L/ha.

Percentage of disease infection was calculated per plant by the equation (stem lesion length)/(total stem length) x 100% (6 plants per plot at random). Scleroonia rot infection was assessed 4 times, 7 days after application A (DAAA) + 7, 14 and 21 DAAB. The area under the translational progression curve (AUDPC) was calculated for each plot using the recorded macroscopic infection data set. Relative AUDPC (% control based on AUDPC) was calculated as percent of untreated control. Results are given in Table 1.

Field Assessment of Colletotrichum capsici (COLLCA) on Pepper:

The evaluation of COLLCA's compound I on capsicum, as a protective and therapeutic modality, was conducted in two separate field trials. A fungicide treatment containing a 5% EC formulation of compound I plus an adjuvant (Trycol, 0.2% v/v to 50% w/w) was applied to pepper plants (CPSAN) 3 times for a 2-day protective test. It was sprayed, and the first application was performed at 43 days after planting during the flowering and fruiting periods, and the next application was performed at 7-day intervals. Formulations of Compound I were applied at active ingredient rates of 50, 100 and 150 grams per hectare (g ai/ha). Experimental plots were inoculated with the anthracnose pathogen 2 days after the single application. The treatment was part of an experimental trial designed as a random complete block with 4 replicates and a plot of approximately 2 x 1 m, and the formulation of Compound I was applied in a water volume of 1000 L/ha.

Disease severity was assessed as the proportion of diseased fruit areas per plant (6 plants per plot at random). Anthrax infection was assessed 4 times, 7 days after application A (DAAA), 7 DAAB + 7 and 14 DAAC. The area under the translational progression curve (AUDPC) was calculated for each plot using the recorded macroscopic infection data set. Relative AUDPC (% control based on AUDPC) was calculated as percent of untreated control. Results are given in Table 1.

For a 4-day therapeutic trial, a fungicide treatment containing a 5% EC formulation of Compound I plus an adjuvant (Trycol, 0.2% v/v to 50% w/w) was applied to pepper plants (CPSAN) in 2 It was sprayed once, and the first application was applied 59 days after planting during the flowering and fruiting periods, and the second application was applied 7 days later. Formulations of Compound I were applied at active ingredient rates of 50, 100, 150 and 200 grams per hectare (g ai/ha). Experimental plots were inoculated with the anthracnose pathogen 4 days prior to single application (for treatment). The treatment was part of an experimental trial designed as a random complete block with 4 replicates and a plot of approximately 2 x 1 m, and the formulation of Compound I was applied in a water volume of 1200 L/ha.

Disease severity was assessed as the proportion of diseased fruit areas per plant (6 plants per plot at random). Anthrax infection was assessed 4 times, 7 days after application A (DAAA), +7, 14 and 21 DAAB. The area under the translational progression curve (AUDPC) was calculated for each plot using the recorded macroscopic infection data set. Relative AUDPC (% control based on AUDPC) was calculated as percent of untreated control. Results are given in Table 1.

Field evaluation of Erysiphe cichoracearum (ERYSCI) on cucumber:

The evaluation of ERYSCI's Compound I on cucumber, both as a protective and as a therapeutic modality, was conducted in two separate field trials. For the 2-day protection test (2DP), a fungicide treatment containing a 5% EC formulation of Compound I plus an adjuvant (Trycol, 50% w/w at 0.2% v/v) was applied to cucumber plants (CUMSA). was sprayed twice, the first application was applied 41 days after planting, during the fruiting period, and the next application was applied 7 days later. Formulations of Compound I were applied at active ingredient rates of 50, 100 and 150 grams per hectare (g ai/ha). Two days after the first application, the experimental plots were inoculated with a powdery mildew pathogen. The treatment was part of an experimental trial designed as a randomized complete block with 4 replicates and a plot of approximately 2 x 1 m, and the formulation of Compound I was applied at a water volume of 1200 L/ha based on seedling size.

Disease severity was assessed as the proportion of diseased areas on cucumber leaves per plant (6 plants per plot at random). Cucumber powdery mildew infection was assessed three times, 7 days after application A (DAAA), and 7 and 14 DAAB. The area under the translational progression curve (AUDPC) was calculated for each plot using the recorded macroscopic infection data set. Relative AUDPC (% control based on AUDPC) was calculated as percent of untreated control. Results are given in Table 1.

For therapeutic trials, a fungicide treatment containing a 5% EC formulation of Compound I plus an adjuvant (Trycol, 0.2% v/v to 50% w/w) was sprayed twice on cucumber plants (CUMSA). , The first application was applied 29 days after planting, during the fruiting period, and the second application was applied 7 days after planting. Formulations of Compound I were applied at active ingredient rates of 50, 100 and 150 grams per hectare (g ai/ha). Experimental plots were inoculated with a powdery mildew pathogen 2 days prior to single application (for treatment). The treatment was part of an experimental trial designed in randomized complete blocks with 4 replicates and a plot of approximately 2 x 1 m, and the formulation of Compound I was applied at a water volume of 1200 L/ha based on seedling size.

Disease severity was assessed as the proportion of diseased areas on cucumber leaves per plant (6 plants per plot at random). Powdery mildew infection was assessed 4 times, 7 days after application A (DAAA), + 7, 14 and 21 DAAB. The area under the translational progression curve (AUDPC) was calculated for each plot using the recorded macroscopic infection data set. Relative AUDPC (% control based on AUDPC) was calculated as percent of untreated control. Results are given in Table 1.

Field evaluation of Alternaria solani (ALTESO) on tomatoes:

Evaluation of ALTESO's compound I on tomatoes was conducted in two separate field trials. In a first trial, a fungicide treatment containing Compound I applied in a 5% EC and 10% SC formulation and tank-mixed with an adjuvant (Agnique BP420, 0.3% v/v to 50% w/w), 100 per hectare and at a rate of 200 grams of active ingredient (g ai/ha), sprayed onto tomato plants (LYPES) at approximately 60-70 cm height. The test was based on 5 foliar applications at 7-day intervals, and the early blight pathogen was inoculated 2 days after one application. The treatment was part of an experimental trial designed as a random complete block with 4 replicates and a plot of approximately 1.5 x 4m. Compound I was applied at a water volume of 1000 L/ha with an AZO backpack sprayer using compressed air.

Disease severity was recorded as the percentage of diseased areas by randomly selecting 20 leaves and 20 fruits per plot. Between 0-35 days after the first application, control was assessed using 6 evaluations performed by DAA1. The area under the translational progression curve (AUDPC) was calculated for each plot using the recorded severity data set. Relative AUDPC (% control based on AUDPC) was calculated as percent of untreated control. Results are given in Table 2.

In a replicated trial, a fungicide treatment containing Compound I applied in a 5% EC and 10% SC formulation and tank-mixed with an adjuvant (Agnique BP420, 50% w/w at 0.3% v/v) was applied in a 5% EC and 10% SC formulation, after planting approximately On day 21, tomato plants (LYPES, cultivar Taylor) were sprayed. Formulations of Compound I were applied at rates of 100 and 200 grams of active ingredient per hectare (g ai/ha). The test was based on 6 foliar applications at 10-day intervals under natural disease pressure of tomato early blight. The treatment was part of an experimental trial designed as a random complete block with 4 replicates and a plot of approximately 2 x 4m. The formulation of Compound I was applied at a water volume of 800 L/ha using a backpack float sprayer (BKPCKENG, Solo 443; HCSOLID - Albutz ATR80 Orange nozzle) and pressurized at 300 psi. Disease severity (control) was recorded as percent visual leaf infection per plot and evaluated 10 days after the last application. Results are given in Table 2.

Field evaluation of Mycovellosiella fulva (FULVFU) on tomatoes:

A 10% SC formulation of Compound I was tank mixed with four different adjuvants: Agnique BP420 (50% w/w at 0.3% v/v); Trycol (0.1% v/v to 50% w/w); Ethomeen T18H (50% w/w at 0.2% v/v); and phase II (50% w/w at 0.2% v/v). The fungicide treatment containing the formulation of Compound I, alone or together with an adjuvant, was sprayed on tomato plants 4 times, with the first application about 3 months after planting and the next 3 applications at 7-10 day intervals. Formulations of Compound I were applied at active ingredient rates of 50, 100, 150 and 200 grams per hectare (g ai/ha). The experimental plots were inoculated with leaf mold pathogens 7 days prior to one application (for treatment). The treatment was part of an experimental trial designed as a random complete block with 4 replicates and a plot of approximately 2.5 x 1.4 m. The formulation of Compound I was applied to a water volume of 675 L/ha.

Disease severity was recorded as percentage of visually diseased leaves (6 random plants per plot). Tomato leaf fungal infection was evaluated 5 times on day 7 after one application (7 DAAA), 7 DAAB, 5 DAAC, followed by 7 and 12 DAAD. The area under the translational progression curve (AUDPC) was calculated for each plot using the recorded severity data set. Relative AUDPC (% control based on AUDPC) was calculated as percent of untreated control. Results are given in Table 3.

Field evaluation of Stagonosporopsis cucurbitacearum (DIDYBR) on watermelon:

A 10% SC formulation of Compound I was tank mixed with four different adjuvants: Agnique BP420 (50% w/w at 0.3% v/v); Trycol (0.1% v/v to 50% w/w); Ethomeen T18H (50% w/w at 0.2% v/v); and phase II (50% w/w at 0.2% v/v). The fungicide treatment containing the formulation of Compound I, alone or together with an adjuvant, was sprayed on watermelon plants 4 times, with one application about 2 months after planting and the next 3 applications at 7-10 day intervals. Formulations of Compound I were applied at active ingredient rates of 50, 100, 150 and 200 grams per hectare (g ai/ha). Experimental plots were inoculated with the gummy stem blight pathogen 2 days after one application. The treatment was part of an experimental trial designed as a random complete block with 4 replicates and a plot of approximately 2.5 x 1.4 m. The formulation of Compound I was applied to a water volume of 675 L/ha.

Disease severity was recorded as length of stem lesions and as percentage of diseased leaves (3 random plants per plot). Watermelon vine blight infection was assessed twice, on day 6 after one application (6 DAAA) followed by 19 DAAD (19 DAAD). The area under the translational progression curve (AUDPC) was calculated for each plot using the recorded severity data set. Relative AUDPC (% control based on AUDPC) was calculated as percent of untreated control. Results are given in Table 4.

Greenhouse evaluation of Botrytis cinerea (BOTRCI) on broad beans:

Technical grade material was dissolved in acetone and then mixed with 9 parts of water containing 100 ppm of Triton X-100. The fungicide formulation was applied onto the seedling plants by runoff using an automated booth sprayer. All sprayed plants were dried 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 areas of the plants was evaluated on a 0-100% disease severity scale. Disease control was calculated using the ratio of disease severity on treated plants compared to untreated plants. Results are given in Table 5.

In each case of Tables 1-5, the rating scale for control rates based on AUDPC is as follows:

Table 1: Control rate by compound I ^a against fungal diseases of vegetables based on area under the translational progression curve (AUDPC) in protective and therapeutic trials. ALTEBI ^b SCLESC ^c COLLCA ^d ERYSCI ^e ratio
(g ai/ha) ^f 2 ^DPg 2DP 2DP 4 DC ^h 2DP 2 DC 50 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 applied as a 5% EC formulation with Trycol adjuvant (50% w/w at 0.2% v/v)

^b Black leaf spots of cabbage - Alternaria brassicicola

^c Lettuce Scleroonia Rot - Sclerotinia Sclerotiorum ( Sclerotinia sclerotiorum )

^d Pepper Anthrax - Colletotrichum capsici

^e Cucumber powdery mildew - Erysiphe cichoracearum

^f grams of active ingredient per hectare

^g 2-day protective test

^h 4-day therapeutic trial

Table 2: Efficacy of compound I ^a against early blight (ALTESO, Alternariasolani ) on tomato leaves and fruits in EC and SC formulations. leaf ^b
try 1 fruit ^c
try 1 leaf ^b
try 2 ratio
(g ai/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 with Agnique BP420 (0.3% v/v to 50% w/w) as adjuvant

^b Disease control rate on tomato leaves based on area under the translational progression curve (AUDPC)

^c Disease control rate for tomato fruit based on area under the translational progression curve (AUDPC)

grams of active ingredient per ^d hectare

Table 3: Efficacy of Compound I against tomato leaf mold (FULVFU, Mycovellosiella fulva ) in 10% SC formulations with and without adjuvant ^a . reinforcer ratio
(g ai/ha) ^b I ^c II ^d III ^e IV ^{f Vg} 50 C A NT NT NT 100 C A A B A 150 NT A NT NT NT 200 NT A NT NT NT

^a Control rate based on area under the translational progression curve (AUDPC)

^b grams of active ingredient per hectare

^c I - no adjuvant

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

^e III - Trycol (50% w/w in 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 of Compound I on watermelon vine blight (DIDYBR, Stagonosporopsis cucurbitacearum ) in 10% SC formulations with and without adjuvant ^a . reinforcer ratio
(g ai/ha) ^b I ^c II ^d III ^e IV ^f V ^g 50 NT A NT NT NT 100 B A B B B 150 NT A NT NT NT 200 NT A NT NT NT

^a Control rate based on area under the translational progression curve (AUDPC)

^b grams of active ingredient per hectare

^c I - no adjuvant

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

^e III - Trycol (50% w/w in 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 broad bean gray mold (BOTRCI, Botrytis cinerea ). ratio
(ppm) ^a Control % ^b 400 A 100 A 25 A 6.25 B

^a parts per million

^b Control rate calculated using the ratio of disease severity on treated plants compared to untreated plants

Field Assessment of Corynespora cassiicola (CORYCA) in Tomatoes:

Fungicide treatment containing compound I applied in SC formulation (with MSO) and tank-mixed with reinforcing agent (Agnique BP-420, 0.2% v/v to 50% w/w or Adsee C80W 80%), 50 per hectare , 75, 100 and 150 grams of active ingredient (g ai/ha) were sprayed on tomato plants (LYPES, Charger cultivar) at the growth stage BBCH64 (fourth flowering). Experimental plots were inoculated with target spot pathogens 1 day after initial application. The treatment was part of an experimental trial designed as a random complete block (RCB) with 4 replicates and a plot of approximately 6 x 25 ft. Compound I was applied at a water volume of 100 gal/acre using a tractor sprayer (SCDISC D1 nozzle) and pressurized at 200 psi.

Disease severity (percentage of visually diseased leaves on the entire plot) was assessed 4 times during the test (days 1-20 after application, DAA). The area under the translational progression curve (AUDPC) was calculated for each plot using the recorded severity data set. Relative AUDPC (% control based on AUDPC) was calculated as percent of untreated control. Results are given in Table 6.

Field evaluation of Colletotrichum coccodes (COLLCA) in tomatoes:

A fungicide treatment containing compound I applied in SC formulations (with MSO) and tank-mixed (Agnique BP-420, 0.2% v/v to 50% w/w or Adsee C80W 80%) with an adjuvant, 50 per hectare , 75, 100 and 150 grams of active ingredient (g ai/ha) were sprayed on tomato plants (LYPES, Roma VS Saladette type cultivars) at growth stage 12 of the vegetable growth stage. Experimental plots were run with natural infestation of the anthrax pathogen, supplemented with booster inoculum approximately 1 day after single application. The treatment was part of an experimental trial designed as a random complete block (RCB) with 4 replicates and a plot of approximately 6.67 x 30 ft. Compound I was applied using a backpack sprayer (carbon dioxide (CO ₂ ), 8004VS FF nozzle) at a water volume of 40 gal/acre and pressurized at 38 psi.

Leaf severity rates were evaluated 3 times during the test (0-23 days after application 1). The area under the translational progression curve (AUDPC) was calculated for each plot using the recorded leaf severity data. Relative AUDPC (% control based on AUDPC) was calculated as percent of untreated control. Results are given in Table 7.

Table 6: Comparison of formulations of compound I tank-mixed with MSO retention or Agnique BP-420 for calculated control of target spots (CORYCA, Corynespora cassiicola ) in tomatoes. Compound I ^a Reinforcement ^{a or b} CORYCA Control % (AUDPC) 50 MSO, 100 ^a 55.2 75 MSO, 150 ^a 56.1 100 MSO, 200 ^a 71.6 150 MSO, 300 ^a 84.0 50 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 g/ha unit rate

^b mL/ha unit rate

Table 7: Comparison of formulations of compound I tank-mixed with MSO retention or Agnique BP-420 for calculated control of anthrax (CORYCA, Colletotrichum coccodes ) in tomatoes. Compound I ^a Reinforcement ^{a or b} COLLCA Control % (AUDPC) 50 MSO, 100 ^a 46.0 75 MSO, 150 ^a 75.5 100 MSO, 200 ^a 92.6 150 MSO, 300 ^a 95.3 50 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 g/ha unit rate

^b mL/ha unit rate

Claims (6)

The risk of contracting a disease, selected from cucurbits, tomatoes, leafy vegetables, potatoes, peppers and broad beans, comprising the step of contacting at least a portion of a plant and/or an area adjacent to the plant with Compound I or a composition comprising Compound I. As a method for controlling fungal diseases in vegetable crops

wherein said compound I is effective against fungal pathogens,
Here, the fungal pathogen is black leaf spot of cabbage ( Alternaria brassicicola ), Sclerotinia rot of lettuce (Sclerotinia sclerotiorum ), and anthracnose of pepper (Cholerotinia sclerotiorum). Colletotrichum capsici ), tomato leaf mold ( Mycobellosiella fulva ), watermelon vine blight ( Stagonosporopsis cucurbitacearum ), broad bean gray A group consisting of pathogens, which are mold ( Botrytis cinerea ), target spot on tomatoes ( Corynespora cassiicola ) and anthracnose on tomatoes ( Colletotrichum coccodes ) Which method is selected from. The method of claim 1 , wherein the composition further comprises at least one additional agriculturally active ingredient selected from the group consisting of insecticides, herbicides, and fungicides. delete delete delete delete