TWI774762B - Use of an acyclic picolinamide compound as a fungicide for control of phytopathogenic fungi in vegetables - Google Patents

Abstract

The present disclosure is related to the field of agrochemicals, including compound I and its use to control fungal diseases in agriculturally useful vegetable crops.

Description

Use of acyclic pyridamides as a fungicide for the control of phytopathogenic fungi in vegetables Cross-references to related applications

This application claims the benefit of US Provisional Patent Application No. 62/500,172, filed on May 2, 2017, the entire contents of which are expressly incorporated herein by reference.

The disclosure of this case is related to ( S )-1,1-bis(4-fluorophenyl)propan-2-yl(3-acetoxy-4-methoxypicolinyl) -L -alanine acid Field of the use of salt for the control of fungal diseases in vegetables.

Fungicides are compounds of natural or synthetic origin that act to protect and treat plants against damage caused by fungi associated with agriculture. In general, there is no single fungicide that can be used in all situations. Therefore, research has continued to produce fungicides with better efficacy, easier use, and lower cost.

The disclosure of this case is related to ( S )-1,1-bis(4-fluorophenyl)propan-2-yl(3-acetoxy-4-methoxypicolinyl) -L -alanine acid Salts (Compound I) and their use as fungicides. Compound I may provide protection against Ascomycetes, Basidiomycetes and Deuteromycetes.

One embodiment of the present disclosure includes a method of controlling a disease in a plant caused by a pathogen, wherein the plant is at risk for disease due to the pathogen, the method comprising contacting the plant or an adjacent area of the plant with a compound comprising Compound I composition.

Another embodiment of the present disclosure is the use of compound I for protecting plants from phytopathogenic organisms, or treating plants infected by phytopathogenic organisms, comprising compound I or a composition comprising compound I are applied to soil, plants, parts of plants, foliage and/or seeds.

In addition, another embodiment of the present disclosure is a composition suitable for protecting plants from phytopathogenic organisms and/or treating plants infected by phytopathogenic organisms, comprising compound I and a botanical acceptable carrier material.

An exemplary embodiment of the present disclosure includes a mixture for controlling fungal growth, the mixture comprising Compound I:

Compound 1 of the present disclosure can be administered by any of a variety of well-known techniques, whether as Compound 1 or in a formulation comprising Compound 1. For example, Compound I can be applied to the roots, stems, seeds, flowers or foliage of plants to control a variety of fungi without harming the commercial value of the plants. Compound I can also be applied by foliar spray, soil spray, soil mix, chemical irrigation, soil irrigation, soil injection or seed treatment. The material may be applied in any of the commonly used formulation types, eg, as a solution, dust, wettable powder, suspendable concentrate or emulsion.

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

The present disclosure contemplates the use of all carriers by which Compound 1 can be formulated for administration and use as a fungicide. Generally, formulations are administered as aqueous suspensions or emulsions. Such suspensions or emulsions can be produced from water-soluble, water-suspendable or emulsifiable preparations, commonly referred to as wettable powders when they are solid; or emulsions, aqueous suspensions when they are liquids. liquid or suspension. It should be readily understood that any material to which Compound 1 can be added can be used provided that it produces the desired effect without significantly interfering with the activity of Compound 1 as an antifungal agent.

Wettable powders which can be compressed into water dispersible granules comprise an intimate mixture comprising Compound I, an inert carrier and a surfactant. The concentration of Compound I in the wettable powder can be from about 10 weight percent to about 90 weight percent, preferably about 25 weight percent to about 75 weight percent, based on the total weight of the wettable powder. In the preparation of wettable powder formulations, Compound I can be compounded with any finely divided solid such as pyrophyllite, talc, chalk, gypsum, fuller's earth, bentonite, magnesia bentonite, starch, cheese Protein, gluten, montmorillonite clay, diatomaceous earth, purified silicate or the like. In this operation, the finely divided carrier and surfactant are typically blended with Compound I and ground.

Emulsions of Compound I may contain a conventional concentration of Compound I in a suitable liquid, such as from about 10 weight percent to about 50 weight percent of Compound I, based on the total weight of the emulsion. Compound I can be dissolved in an inert carrier, which is a water-miscible solvent or a mixture of a water-immiscible organic solvent and an emulsifier. The concentrates can be diluted in water as well as in oils to form spray mixtures in the form of oil-in-water emulsions. Suitable organic solvents include aromatics, especially 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 can also be used.

The emulsifiers that can be advantageously employed herein, can be readily determined by those skilled in the art, and include various nonionic, anionic, cationic and amphoteric emulsifiers, or a blend of two or more emulsifiers thing. Examples of nonionic emulsifiers useful for preparing emulsions include polyolefin glycol ethers, and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines, or fatty acids with ethylene oxides, propylene oxides, such as ethoxylates Alkylated alkylphenols and carboxylates dissolved with polyols or polyoxymethylenes. 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 polyethylene glycol ethers, and suitable salts of phosphated polyethylene glycol ethers.

Representative organic liquids that can be used to prepare the emulsions of Compound I of the present invention are aromatic liquids such as xylene, propylbenzene fractions; or mixed naphthalene fractions, mineral oil, substituted aromatic organic liquids such as dioctyl phthalate ; kerosene; dialkylamides of various fatty acids, especially fatty diols and dimethylamides of ethylene glycol derivatives, such as n -butyl, ethyl or methyl ethers of diethylene glycol, And the methyl ether of triethylene glycol and the like, and so on. Mixtures of two or more organic liquids can also be used to prepare emulsions. Organic liquids include xylene and propylbenzene fractions, with xylene being the best in some cases. Surface-active dispersants are generally used in liquid formulations in dosages from 0.1 to 20 weight percent, based on the weight of the dispersant combined with Compound I. The formulations may also contain other compatible additives such as plant growth regulators and other biologically active compounds used in agriculture.

Aqueous suspensions of Compound I are included, dispersible in aqueous vehicles, in concentrations ranging from about 5 to about 50 weight percent, based on the total weight of the aqueous suspension. Suspensions are prepared by grinding Compound I finely and vigorously mixing the ground material in a carrier comprising water and a surfactant selected from the same types described above. Other ingredients such as inorganic salts and synthetic or natural gums can also be added to increase the density and viscosity of the aqueous carrier.

Compound I can also be applied in the form of a granular formulation which is particularly suitable for application to soil. Granular formulations typically contain from about 0.5 to about 10 percent by weight (based on the total weight of the granular formulation of Compound I) dispersed in an inert carrier composed in whole or in large part of coarsely divided inert materials, Inexpensive substances such as magnesia bentonite, bentonite, diatomaceous earth, clay or similar. Such formulations are generally prepared by dissolving Compound I in a suitable solvent and applying it to a particulate carrier which has been preformed in a suitable particle size (in the range from about 0.5 to about 3 mm). Suitable solvents are solvents in which Compound I is substantially or completely soluble. Such formulations can also be prepared by forming the carrier and Compound I and solvent into a paste or paste, and crushing and drying to obtain the desired granular particles.

Preparation of Powders Containing Compound I Compound I in powder form can be mixed intimately with a suitable powdered agricultural carrier such as, for example, kaolin, 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.

The formulations may additionally contain co-surfactants to enhance the deposition, wetting and penetration of Compound I on target crops and organisms. These co-surfactants can optionally be used as a formulation component or as a keg mix. The dosage of cosurfactant generally varies from 0.01 to 1.0 volume percent, preferably 0.05 to 0.5 volume percent (based on the spray volume of water). Suitable co-surfactants include, but are not limited to, ethoxylated nonylphenols, ethoxylated synthetic or natural alcohols, esters or salts of sulfosuccinic acid, ethoxylated organosilicones, ethoxylated fats Amines and blends of surfactants with mineral or vegetable oils. The formulations may also include oil-in-water emulsions, such as those disclosed in US Patent Application No. 11/495,228, the disclosure of which is expressly incorporated herein by reference.

In certain instances, it may be beneficial to spray the formulation of Compound I by aerial application using an airplane or helicopter. The exact composition of these aerial applications depends on the crop being treated. The spray volume to be used for aerial application of vegetables, preferably from 15 to 50 liters per hectare (L/ha), with addition of standard surfactant, wettability, adhesion, spreading or penetrating types Compounds such as non-ionic surfactants, silicones or crop oil concentrates, preferably from 0.05 to 15 percent, based on the spray volume of water.

The formulation may optionally include combinations with other pesticide compounds. Such additional pesticide compounds may be fungicides, insecticides, herbicides, nematicides, acaricides, arthropodicides, bactericides, additives such as nonionic surfactants, organosilicones or Crop oil concentrates, or combinations thereof, are compatible with the compounds of the present invention in the medium chosen for application and are not antagonistic to the activity of the compounds of the present invention. Thus, in such embodiments, the other pesticidal compounds are used as supplemental poisons for the same or a different pesticidal use. The combination of Compound I and the pesticide compound can generally be present in a weight ratio of from 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 combination with other fungicides, the compounds I as claimed in the present invention can be formulated with other fungicides, mixed with other fungicides in a jar, or applied sequentially with other fungicides. Such other fungicides may include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenol, 8-hydroxyquinyl sulfate, ametoctradin, amisulbrom ), antimycin, Ampelomyces quisqualis , azaconazole, azoxystrobin, Bacillus subtilis , Bacillus subtilis strain QST713, benalaxyl, Benomyl, benthiavalicarb-isopropyl, benzylaminobenzene-sulfonic acid (BABS) salt, bicarbonate, biphenyl, bismerthiazol, bitertanol, Bixafen, blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole, bupirimate, calcium polysulfide), captatol, captan, carbendazim, carboxin, carpropamid, carvone, clomethano (chlazafenone), chloroneb, chlorothalonil, chlozolinate, Coniothyrium minitans , copper hydroxide, copper octoate, copper oxychloride ), copper sulfate, copper sulfate (ternary), cuprous oxide, cyazofamid, cyflufenamid, cvmoxanil, cyproconazole, cyprodinil , dazomet, debacarb, diammonium ethylenebis-(dithiocarbamate), dichlofluanid, dichlorophen, diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole, difenzoqua t ion), diflumetorim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, white powder ( dinocap), diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine, dodidine free base, edifenphos, instazobine ( enestrobin, enestroburin, epoxiconazole, ethaboxam, ethoxyquin, etridiazole, famoxadone, imidazole fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, benzene fenpropidin, fenpropimorph, fenpyrazamine, fentin, fentin acetate, fentin hydroxide, dimethylamine Ferric methylthiocarboxylate (ferbam), ferimzone, fluazinam, fludioxonil, flumorph, fluopicolide, fluopyram (fluopyram), fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, Flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl, fosetyl-aluminium, wheat ears Fuberidazole, furalaxyl, furametpyr, guazatine, guazatine acetate, GY-81, hexachlorobenzene, hexaconazole, sterilization Ning (hymexazol), Equatorial (imazalil), imibenconazole, iminoctadine, triacetate, albesilate, albesilate iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalicarb, isoprothiolane, napypyr Amine (isopyrazam), isotianil, kasugamycin, kasugamycin hydrochloride, kresoxim-methyl, laminarin, mancopper ), mancozeb, mandipropamid, maneb, mefenoxam, mepanipyrim, mepronil, meptyl -dinocap), mercuric chloride, mercuric oxide, mercurous chloride, metalaxyl, metalaxyl-M, metam, metam-ammonium, metam- Potassium, Sodium, Metconazole, Methasulfocarb, Iodomethane, Methyl Isothiocyanate, Metiram, Metominostrobin, Methophen Metrafenone, mildiomycin, myclobutanil, nabam, nitrothal-isopropyl, nuarimol, octhilinone, Ofurace, oleic acid (fatty acids), orysastrobin, oxadixyl, oxine-copper, oxpoconazole fumarate, Oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad (penthiopyrad), phenylmercuric acetate, phosphonic acid, phthalide, picoxystrobin, Granomycin (A) (polyoxin B), granulomycin (polyoxins), granulomycin (D) (polyoxorim), potassium bicarbonate (potassium bicarbonate), potassium hydroxyquinoline sulfate (potassium hydroxyquinoline sulfate), culling Probenazole, prochloraz, procymidone, propamocarb, propiconazole, propiconazole, propineb, proquinazid, Prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriofenone, pyroquilon, quinoclamine, quinoxyfen, quintozene ), Polygonum (Reynoutria sachalinensis) extract, sedaxane, silthiofam, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, pentachlorobenzene oxide Sodium, spiroxamine, sulfur, SYP-Z048, tars, tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, methyl efalin (tolylfluanid), triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, Triforine, Triphenyltin Hydroxide ltin hydroxide), triticonazole, validamycin, valifenalate, valiphenal, vinclozolin, zineb, fome Zinc (ziram), zoxamide, Candida oleophila , Fusarium oxysporum , Gliocladium species, Phlebiopsis gigantea , 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-nitro propane, 2-(2-heptadecyl-2-imidazolin-1-yl)ethanol, 2,3-dihydro-5-phenyl-1,4-dithi1,1,4,4- Tetraoxide, 2-methoxyethylmercury acetate, 2-methoxyethylmercury chloride, 2-methoxyethylmercury silicate (2-methoxyethylmercury chloride) methoxyethylmercury silicate), 3-(4-chlorophenyl)-5-methylrhodamine, 4-(2-nitroprop-1-enyl)phenyl thiocyanate, aminopyrifen ), ampropylfos, anilazine, azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox, benzothiazine Bentaluron, benzamacril; benzamacril-isobutyl, benzamorf, benzovindiflupyr, binapacryl, bisulfate (methyl mercury), bis(tributyltin oxide), butiobate, cadmium calcium copper zinc zinc chromate sulfate, carbamorph, CECA, gram chloride ( chlobenthiazone), diamine (chlor) aniformethan), chlorfenazole, chlorquinox, climbazole, bis(3-phenylsalicylic acid) copper, copper-zinc chromate, coumoxystrobin, sulfur Cufraneb, cupric hydrazinium sulfate, cuprobam, cyclafuramid, cypendazole, cyprofuram, decafentin, Dichlobentiazox, dichlone, dichlozoline, diclobutrazol, dimethirimol, dinocton , dinosulfon, dinoterbon, dipymetitrone, dipyrithione, ditalimfos, dodicin, hydrazide ( drazoxolon), EBP, enoxastrobin, ESBP, etaconazole, etem, ethirim, fenaminosulf, fenaminstrobin , Fenapanil, Fenitropan, Fenpicoxamid, Fluindapyr, Fluopimide, Fluotrimazole , flufenoxystrobin, furcarbanil, furconazole, cis-fuconazole, furmecyclox, furophanate (glyodine), griseofulvin, halacrinate, Hercules 3944, hexylthiofos, ICIA0858, inpyrfluxam, ipfentrifluconazole, ipflufenoquin, isofetamid, isoflucypram , isopamphos, isovaledione, mandestrobin, mebenil, mecarbinzid, mefentrifluconazole, Metazoxolon, methfuroxam, methylmercury dicyamdiamide, metsulfovax, metyltetraprole, milneb, viscose Mucochloric anhydride, myclozolin, N -3,5-dichlorophenyl-succinimide, N -3-nitrophenylitaconimide, natamycin (natamycin), N -ethylmercury-4-toluenesulfoaniline, nickel bis(dimethyldithiocarbamate), OCH, oxathiapiprolin, dimethyldithioamine Phenylmercury formate, phenylmercury nitrate, phosdiphen, picarbutrazox, prothiocarb; thiocarbamate hydrochloride, pydiflumetofen, pyran ( pyracarbolid, pyrapropoyne, pyraziflumid, pyridachlometyl, pyridinitril, pyrisoxazole, chloromethoxypyridine ( pyroxychlor, pyroxyfur, quinacetol, quinocetone sulfate, quinazamid, quinconazole, quinofumelin, rabenzazole, Salicylanilide, SSF-109, sultropen, tecoram, thiadifluor, thicyofen, thiochlorfenphim , thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trichlamide ), chlorpyrifos triclopyricarb, triflumezopyrim, urbacid, zarilamid and any combination thereof.

In addition, Compound I of the present invention can be combined with other pesticides to form pesticide mixtures and synergistic mixtures thereof, wherein the other pesticides are compatible with Compound I of the present invention without antagonizing the activity of Compound I, including in the medium of choice for application insecticides, nematicides, acaricides, arthropodicides, fungicides or combinations thereof. Compound I of the present disclosure can be applied in combination with one or more other pesticides to control a wider variety of unwanted pests. When used in combination with other pesticides, the compound I claimed in this case can be formulated with other pesticides, mixed with other pesticides in a medicine drum, or applied sequentially with other pesticides. Representative insecticides include, but are not limited to: antibiotic insecticides such as allosamidin and thuringiensin; macrolide insecticides such as spinosad and spinetoram; avermectin insecticides such as abamectin, doramectin, emamectin, eprinomectin ), ivermectin and selamectin; milbermycin insecticides such as lepimectin, milbemectin, milbemycin oxime) moxidectin; carbamate insecticides such as bendiocarb and carbaryl; benzofuran methyl carbamate insecticides such as bendiocarb Benfuracarb, carbofuran, carbofuran, decarbofuran and furathiocarb; dimethylcarbamate ) Dimitan, dimetilan, hyquincarb and pirimicarb; oxime carbamate insecticides such as alanycarb, aldicarb, aldoxycarb, butocarboxim, butoxycarboxim, methomyl, nitrilacarb, oxamyl, tazimcarb ), thiocarboxime, thiodicarb and thiofanox; benzoic carbamic acid insecticides , such as allyxycarb, aminocarb, co-kill Bufencarb, butacarb, carbanolate, cloethocarb, dicresyl, dioxacarb, EMPC, ethiofencarb, Fenethacarb, Fenobucarb, Isoprocarb, Methiocarb, Methicarb Metolcarb, mexacarbate, promacyl, promecarb, propoxur, trimethacarb, XMC and xylylcarb; desiccant Insecticides such as boric acid, diatomaceous earth and silica gel; diamine insecticides such as broflanilide, chlorantraniliprole, cyanogen cyantraniliprole, cyclaniliprole, cyhalodiamide, flubendiamide, tetrachlorantraniliprole and tetraniliprole; two Diarylisoxazoline insecticides such as fluxametamide; dinitrophenol insecticides such as dinex, dinoprop, dinosam ) and DNOC; Fluorine insecticides such as bariurm hexafluorosilicate, cryolite, sodium fluoride, sodium hexafluorosilicate and sulfluramid; formamidine insecticides , Amitraz, chlordimeform, formetanate and forrnparanate; fumigant insecticides , such as acrylonitrile, carbon disulfide, tetrachloride Carbon (carbon tetrachloride), chloroform, chloropicrin (chloropicrin), p-dichlorobenzene, 1,2-dichloropropane, ethyl formate (ethyl formate), ethylene dibromide (ethylene dibromide), dichloroethane ( ethylene dichloride), ethylene oxide (ethylene oxide), hydrogen cyanide (hydrogen cyanide), iodomethane (iodomethane), methyl bromide (methyl bromide), methyl chloroform (methylchloroform), methylene chloride (methylene chloride), naphthalene ( naphthalene), phosphine (phosphine), sulfuryl fluoride (sulfuryl fluoride) and tetrachloroethane (tetrachlor oethane); inorganic pesticides such as borax, calcium polysulfide, copper oleate, mercurous chloride, potassium thiocyanate, and sodium thiocyanate ; Chitin synthesis inhibitors , such as bistrifluron, buprofezin, chlorfluazuron, cyromazine, diflubenzuron, fluorocyclamide ( flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron ) and triflumuron; youth hormone analogs such as epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene ( methoprene, pyriproxyfen, and triprene; juvenile hormones , such as juvenile hormone I, juvenile hormone II, and juvenile hormone III; mesoionic insecticides, such as dicloromezotiaz and triflumezopyrim; ecdysteroid binding agents such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide ); moulting hormones such as alpha-ecdysone and ecdysterone; moulting inhibitors such as diofenolan; precocenes such as precocenes I, Precogenin II and Precogenin III; unclassified insect growth regulators such as dicyclanil; nereistoxin analogue insecticides such as bensultap ), cartap, thiocyclam and thiosultap; pyridyloyrazole insecticides such as tyclopyrazoflor; nicotine insecticides such as flonicamid; nitroguanidines Insecticides such as clothianidin, dinotefuran, imidacloprid and thiamethoxam; nitromethylene insecticides such as nitenpyram ( nitenpyram and nithiazine; aminopicoline insecticides such as acetamiprid, cycloxaprid, imidacloprid, nitenpyram and thiacloprid; organochlorine pesticides such as bromo-DDT, camphechlor, DDT, pp'-DDT, ethyl-DDD, HCH, gamma-HCH (gamma-HCH), lindane (lindane), methoxychlor (methoxychlor), pentachlorophenol (pentachlorophenol) and TDE; cyclodiene insecticides such as aldrin, bromocyclen, chlorbicyclen, chlorine chlordane, chlordecone, dieldrin, dilor, endosulfan, alpha-endosulfan, endrin, HEOD, heptachlor, HHDN, isobenzan, isodrin, kelevan and mirex; organophosphorus pesticides such as bromophenylene Phosphorus (bromfenvinfos), chlorfenvinphos, crotoxyphos, dichlorvos, dicrotophos, dimethylvinphos, fospirate, Heptenophos, Methocrotophos, Mevinphos, Monocrotophos, Naled, Naftalofos, Phosphamidon, Propionate Propaphos, TEPP and tetrachlorvinphos ; Organothiophosphate insecticides such as dioxabenzofos, fosmethilan and phenthoate; linear alkane organothiophosphate insecticides such as acethion ), amiton, cadusafos, chlorethoxyfos, chlormephos, demephion, tianle phosphorus-O, tianle phosphorus-S, Phosphorus (demeton), Phosphorus-O, Phosphorus-S, Phosphorus-Methyl, Phosphorus-O-methyl, Phosphorus-S-methyl, Phosphorus-S-methyl Base sulfur, disulfoton, ethion, ethopropos, IPSP, isothioate, malathion, methacrifos, methacrifos oxydemeton-methyl, oxydeprofos, oxydisulfoton, phorate, sulfotep, terbufos and thiometon; straight chain Amine organothiophosphate insecticides such as amidithion, cyanthoate, dimethoate, ethoate-methyl, formothion, Mecarbam, omethoate, prothoate, sophamide, and vamidothion; oxime-based organothiophosphates such as chlorphoxim ), phoxim, and phoxim-methyl; heterocyclic organothiophosphate insecticides , such as azamethiphos, coumaphos, worms Phosphorus (coumithoate), Dioxathion, Endothion, Menazon, Morphos, Phosalone, Pyraclofos, Bifensone pyridaphenthion and quinothion; benzothiopyran organothiophosphate insecticides Insecticides such as dithicrofos and thicrofos; benzotriazole Azinphos-organothiophosphate insecticides such as azinphos-ethyl and azinphos-ethyl Phosphorus (azinphos-methyl); isoindole organothiophosphate insecticides such as dialifos and phosmet; isoxazole organothiophosphate insecticides such as isoxathion and zolaprofos; pyrazolopyrimidine organothiophosphates such as chlorprazophos and pyrazophos; pyridine organothiophosphates Insecticides such as chlorpyrifos and chlorpyrifos-methyl; pyrimidine organothiophosphates such as butathiofos, diazinon, ethoxypyr Phosphorus (etrimfos), pyrimiphos (lirimfos), pirimiphos-ethyl (pirimiphos-ethyl), pyrimiphos-methyl, primidophos (primidophos), pyrimitate and butylpyrimidine Phosphorus (tebupirimfos); benzopyrazine organothiophosphate hydrochloride insecticides , such as quinalphos and quinalphos-methyl; thiadiazole organothiophosphate insecticides , such as moxa Athidathion, lythidathion, methidathion, and prothidathion; triazole organothiophosphate insecticides , such as isazofos and triazophos ); Phenylorganothiophosphate insecticides such as azothoate, bromophos, bromophos-ethyl, carbophenothion, chlorthiophos , cyanophos, cythioate, dicapthon, dichlofenthion, etaphos, famphur, fenchlorphos, Fenitrothion, fensulfothion, fenthion, fenthion-ethyl, heterophos, jodfenphos, fenthion Mesulfenfos, parathion, parathion-methyl, phenkapton, phosnichlor, profenofos, thiophanate Prothiofos, sulprofos, temephos, trichlormetaphos-3 and trifenofos; phosphonate insecticides such as Butonate and trichlorfon; thiophosphate insecticides , such as mecarphon; phenylethyl thiophosphate insecticides , such as terresin ( fonofos and trichloronat; phenylphenyl thiophosphate insecticides such as cyanofenphos, EPN and leptophos aminophosphate insecticides such as gram Crufomate, fenamiphos, fosthietan, mephosfolan, phosfolan, and pirimetaphos; thionamides Insecticides such as acephate, isocarbophos, isofenphos, isofenphos-methyl, methamidophos and pamiphos ( propetamphos); phosphamide insecticides , such as dimefox , mazidox, mipafox, and schradan; oxadiazines, such as Indoxacarb; oxadrazoline insecticides such as metoxadiazone; phthalimide insecticides such as dialifos, phosmet ) and tetramethrin; pyrazole-type insecticides such as tebufenpyrad, tolefenpyrad; phenpyrazole -type insecticides such as acetoprole, acetaminophen Ethiprole, fipronil, pyrafluprole, pyriprole and vaniliprole; pyrethroid insecticides such as acrinathrin, Allethrin, bioallethrin, barthrin, bifenthrin, kappa-bifenthrin, bioethanomethrin, dextran Permethrin (chlor oprallethrin), cyclethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyfluthrin ( gamma-cyhalothrin), λ-cyhalothrin (lambda-cyhalothrin), cypermethrin, α-cyhalothrin, β-cyhalothrin, θ-cyhalothrin, ζ-cyhalothrin, cyphenin (cyphenothrin), deltamethrin, dimefluthrin, dimethrin, empenthrin, fenfluthrin, fenpirithrin, Fenpropathrin, fenvalerate, esfenvalerate, flucythrinate, fluvalinate, tau-fluvalinate, furfural (furethrin), heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, ε-Metofluthrin Epsilon-metofluthrin, momfluorothrin, epsilon-momfluorothrin, permethrin, biopermethrin, transpermethrin, phenothrin, prallethrin, profluthrin, pyresmethrin, resmethrin, bioresmethrin, cis cismethrin, tefluthrin, kappa-tefluthrin, terallethrin, tetramethrin, tetrafluthrin tetramethylfluthrin, tralomethrin, and transfluthrin; pyrethrin insecticides such as etofenprox, fluthrin fenprox, halfenprox, protrifenbute and silafluofen; pyrimidinamine insecticides such as flufenerim and pyrimidifen; pyrrole insecticides pesticides such as chlorfenapyr; tetramic acid pesticides such as spiropidion and spirotetramat; ketobutyrolactone pesticides such as spiro spiromesifen; thiourea insecticides , such as diafenthiuron; urea insecticides , such as flucofuron and sulcofuron; unclassified unclassified nematicides , such as fluazaindolizine and tioxazafen; and unclassified insecticides , such as benzpyrimoxan, closantel , Copper naphthenate, Crotamiton, EXD, Fenazaflor, Fenoxacrim, Fluhexafon, Fowler Reason name (flupyrimin), hydramethylnon, isoprothiolane, malonoben, metaflumizone, nifluridide, oxazolsulfyl, Plifenate, pyridaben, pyridalyl, pyrifluquinazon, rafoxanide, sulfoxaflor, benzene Triarathene and triazamate and any combination thereof.

In addition, Compound I of the present invention can be combined with other herbicides to form pesticide mixtures and synergistic mixtures thereof, wherein the other herbicide is compatible with Compound I of the present invention without antagonizing the activity of Compound I in the medium in which it is selected for application . The fungicidal Compound I of the present disclosure can be applied in combination with one or more herbicides to control a wider variety of unwanted plants. When used in combination with other herbicides, Compound I claimed herein can be formulated with the other herbicides, mixed with the other herbicides in a pail, or applied sequentially with the other herbicides. Representative herbicides include, but are not limited to: amide herbicides such as allidochlor, beflubutamid, benzadox, benzipram, bromobutamid Bromobutide, cafenstrole, CDEA, cyprazole, dimethenamid, dimethenamid-P, diphenamid, three Epronaz, etnipromid, fentrazamide, flupoxam, fomesafen, halosafen, butamidamide (isocarbamid), isoxaben, napropamide, naptalam, pethoxamid, propyzamide, quinonamid, amichlor (tebutam) and tiafenacil; benzalkonium herbicides such as chloranocryl, cisanilide, clomeprop, cypromid, pyridoxine diflufenican, etobenzanid, fenasulam, flufenacet, flufenican, mefenacet, fomefenacet Mefluidide, metamifop, monalide, naproanilide, pentanochlor, picolinafen and propanil; Phenylalanine herbicides , such as benzoylprop, flamprop, and flamprop-M; chloroacetanilide herbicides , such as acetochlor, alachlor , Butachlor, Butenachlor, Delachlor, Diethatyl, Dimethachlor, Metazachlor, Mo Metolachlor, S-metolachlor, Pretilachlor, Propachlor, propisochlor, prynachlor, terbuchlor, thenylchlor and xylachlor; thiobenzyl Amide herbicides such as benzofluor, perfluidone, pyrimisulfan and profluazol; sulfonamide herbicides such as asulam, carba Carbasulam, fenasulam and oryzalin; thioamide herbicides such as chlorthiamid; antibiotic herbicides such as bilanafos; Benzoic acid herbicides , such as chloramben, dicamba, 2,3,6-TBA, and tricamba; pyrimoxybenzoic acid herbicides, such as bispyribac ) and pyriminobac; pyrimidine thiobenzoic acid herbicides such as pyrithiobac; phthalic acid herbicides such as chlorthal; pyridine formate herbicides such as chloramines aminopyrald, clopyralid, florpyrauxifen, halauxifen and piclorarm; quinoline carboxylic acid herbicides such as quinclorac ) and quinmerac; arsenic herbicides such as cacodylic acid, CMA, DSMA, hexaflurate, MAA, MAMA, MSMA, potassium arsenite and Sodium arsenite; benzalkonium cyclohexanedione herbicides such as fenquinotrione, lancotrione, mesotrione, sulcotrione ), tefuryltrione and tembotrione; benzofuran alkyl sulfonate herbicides, such as benfuresate and ethofumesate; benzothiazole herbicides, such as benzazolin; carbamate herbicides such as asulam, carboxazoe, chlrprocarb, di chlormate), fenasulam, karbutilate, and terbucarb; phenylcarbamate herbicides such as barban, BCPC, carbasulam , carbetamide, CEPC, chlorbufam, chlorpropham, CPPC, desmedipham, phenisopham, phenmedipham, betaine-ethyl phenmedipham-ethyl, propham, swep; cyclohexenoxime herbicides, such as alloxydim, butroxydim, clethodim, Cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, and tralkoxydim; cyclopropylisoxin azole herbicides such as isoxachlortole and isoxaflutole; dimethylimide herbicides such as cinidon-ethyl, flumezin , flumiclorac, flumioxazin and flumipropyn; dinitroaniline herbicides such as benfluralin, butralin, taran Dinitramine, ethalfluralin, fluchloralin, isopropalin, methalpropalin, nitralin, oryzalin, Pendimethalin, prodiamine, profluralin and trifluralin; dinitrophenol herbicides such as dinofenate, dinoprop, amylose dinosam, dinoseb, dinoterb, DNOC, etinofen and medinoterb; diphenyl ether herbicides such as ethoxyfen ); nitrophenyl ether herbicides such as acifluorfen, aclon ifen), bifenox, chlomethoxyfen, chlornitrofen, etnipromid, fluorodifen, fluoroglycofen, Fluoronitrofen, fomesafen, furyloxyfen, halosafen, lactofen, nitrofen, trifluorfen nitrofluorfen and oxyfluorfen; dithiocarbamate herbicides such as dazomet and metam; halogenated alkane herbicides such as alorac ), chloropon, dalapon, flupropanate, hexachloroacetone, iodomethane, methyl bromide, monochloroacetic acid, SMA and TCA ; Imidazolinone herbicides such as imazamethabenz, imazamox, imazapic, imazapyr, imazaquin and imazethapyr ); inorganic herbicides such as ammonium sulfamate, borax, calcium chlorate, copper sulfate, ferrous sulfate, potassium azide, cyanide Potassium cyanate, sodium azide, sodium chlorate and sulfuric acid; nitrile herbicides such as bromobonil, bromoxynil, Chloroxynil, cyclopyranil, dichlobenil, iodobonil, ioxynil and pyraclonil; organophosphorus herbicides agents such as amiprofos-methyl, anilofos, bensulide, bilanafos, butamifos, 2,4-DEP, DMPA, EBEP, regulated phosphine (fosami ne), glufosinate, glufosinate-P, glyphosate and piperophos; phenoxy herbicides such as bromofenoxim, barnyardgrass Clomeprop, 2,4-DEB, 2,4-DEP, difenopenten, disul, erbon, etnipromid, phenth fenteracol and trifopsime; oxadiazoline herbicides such as methazole, oxadiargyl, oxadiazon; oxadiazoline azole herbicides , such as fenoxasulfone; 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, 2,4-dichlorprop, 2,4-dichlorprop-P, 3,4-DP, 2,4,5-dichlorprop Fenoprop, mecoprop, and mecoprop-P; aryloxyphenoxypropionic herbicides , such as chlorazifop, clodinafop, chlorine Clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop ), fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, Metamifop, propaquizafop, quizalofop, quizalofop-P and trifop; phenylenediamine herbicides such as taranil (dinitramine) and aniline (prodiamine); pyrazole herbicides such as pyroxasulfone; benzopyrazole herbicides such as benzofenap, pyrazol rasulfotole), pyrazolynate, pyrazoxyfen, tolpyralate, and topramezone; tonpyrazole herbicides such as fluazolate ), nipyraclofen, pioxaden and pyraflufen; pyridazine herbicides such as credazine, cyclopyrimorate, pyridazine pyridafol and pyridate; pyridazinone herbicides such as brompyrazon, chloridazon, dimidazon, flufenpyr, metflurazon, norflurazon, oxapyrazon, and pydanon; pyridine herbicides such as aminopyralid, cliodinate ), clopyralid, dithiopyr, florpyrauxifen, fluroxypyr, halauxifen, haloxydine, bik picloram, picolinafen, pyriclor, thiazopyr and triclopyr; diaminopyrimidine herbicides such as iprymidam ) and tioclorim; quaternary amine herbicides such as cyperquat, diethamquat, difenzoquat, diquat, morfamquat and paraquat; thiocarbamate herbicides such as butylate, cycloate, di-allate, EPTC, esprocarb, Ethiolate, isopolinate, methiobencarb, molinate, orbencarb, pebulate, prosulfocarb, pyributicarb, sulfalate, thiobencarb, zhongcaodan tiocarbazil, tri-allate and vernolate; thiocarbonate herbicides such as dimexano, EXD and proxan; thiourea herbicides such as Methiuron; triazine herbicides such as dipropetryn, indaziflam, triaziflarm and trihydroxytriazine; chlorotriazine herbicides such as atrazine, chlorazine, cyanazine, cyprazine, eglinazine, ipazine, meprazine ( mesoprazine, procyazine, proglinazine, propazine, sebuthylazine, simazine, terbuthylazine, and oxalazine ( trietazine); methoxytriazine herbicides such as atraton, metometon, prometon, secbumeton, simeton and methometon terbumeton; methylthiotriazine herbicides such as ametryn, aziprotryn, cyanatryn, desmetryn, dimethametryn, Meprotryne, prometryn, simetryn, and terbutryn; triazinone herbicides such as ametridione, amibuzin, phenanthrene Hexazinone, isomethiozin, metamitron, metribuzin, and trifludimoxazin; triazole herbicides such as amitrole , cafenstrole, epronaz, and flupoxam; triazolone herbicides , such as amicarbazone, bencarbazone, flufenoxam (carfentrazone), flucarbazone, triazole aniline (ipfencarbazone), propoxy propoxycarbazone, sulfentrazone, and thiencarbazone-methyl; triazole pyrimidine herbicides , such as cloransulam, diclofenac ( diclosulam), florasulam, flumetsulam, metosulam, penoxsulam and pyroxsulam; uracil herbicides , such as benzfendizone, bromacil, butafenacil, flupropacil, isocil, lenacil, sofloxacin Saflufenacil and terbacil; urea herbicides such as benzthiazuron, cumyluron, cycluron, dichloralurea, dichloralurea (diflufenzopyr), isonoruron, isouron, methabenzthiazuron, monisouron and noruron; }phenylurea herbicides , such as anisuron, buturon, chiorbromuron, chloreturon, chlorotoluron, chloroxuron, daimuron, Difenoxuron, dimefuron, diuron, fenuron, fluometuron, fluothiuron, isoproturon, There are linuron, methiuron, methyldymron, metobehzuron, metobromuron, metoxuron, monolinuron, monuron, neburon, parafluron, phenobenzuron, siduron, tetrafluron and thidiazuron; pyrimidine Thiourea herbicides such as sulfonamides Amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron , Flucetosulfuron, Flupyrsulfuron, Foramsulfuron, Halosulfuron, Imazosulfuron, Mesosulfuron ), metazosulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron ( propyrisulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, and trifloxysulfuron; triazine thioureas Herbicides such as chlorsulfuron, cinosulfuron, ethametsulfuron, iodosulfuron, iofensulfuron, metsulfuron, flusulfuron Prosulfuron, thifensulfuron, triasulfuron, tribenuron, triflusulfuron, and tritosulfuron; thiazide herbicides , such as buthiuron, ethidimuron, tebuthiuron, thiazafluron and thidiazuron; and unclassified herbicides such as acrolein, allyl alcohol (allyl alcohol), aminocyclopyrachlor, azafenidin, bentazone, benzobicyclon, bicyclopyrone, buthidazole, cyanide calcium amide (calcium cyanide) amide), cambendichlor, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, cinmethylin, clomazone ( clomazone), CPMF, cresol, cyanamide, cyclopyrimorate, o -dichlorobenzene, dimepiperate, endothal, fluoromidine , fluridone, flurochloridone, flurtamone, fluthiacet, indanofan, methyl isothiocyanate, OCH , oxaziclomefone, pentachlorophenol, pentoxazone, phenylmercury acetate, prosulfalin, pyribenzoxim , pyriftalid, quinoclamine, rhodethanil, sulglycapin, thidiazimin, tridiphane, trimeturon ), tripropindan and tritac.

The compounds I according to the invention may also comprise further active compounds, or be administered jointly and/or sequentially with other active compounds. These other compounds can be plant health stimulants, such as organic compounds, inorganic fertilizers, or micronutrient donors, or other preparations that can affect plant growth, such as inoculants.

In another embodiment, Compound I may also comprise other biological organisms, or may be administered together and/or sequentially with other biological organisms, such as, but not limited to, by Bacillus strains , such as Bacillus subtiis var. amyloliquefaciens FZB24 (TAEGRP ^® ) and Bacillus amyloiquefaciens FZB42 (RHIZOVITAL ^® ), VotiVo ^TM Bacillus firmus (Bacillus firmus), Clariva ^TM (Pasteur ® ) Pasteuria nishizawae), Bacillus thuringiensis, Trichoderma species, and/or mutants and metabolites of each strain exhibiting activity against insects, mites, nematodes and/or phytopathogens formed groups.

One embodiment of the present disclosure is a method for controlling or preventing fungal attack. This method comprises applying a fungicidally effective amount of Compound I to the soil, plant, roots, foliage, seeds or the locus of the fungus, or the locus where infection is to be prevented (eg, to cereals or grape plants). Compound I is suitable for the treatment of a variety of plants at the fungal level while exhibiting low phytotoxicity. Compound I is suitable for use as a protective or therapeutic agent.

Compound I has been found to have significant fungicidal action, especially in agricultural applications. 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, improved plant health; improved plant yield ( eg, increased biomass and/or increased levels of valuable components); improved plant vigor ( eg , improved plant growth and/or greener leaves); improved Plant qualities ( eg, improving the content or composition of certain ingredients); and improving plant tolerance to abiotic and/or biotic stress.

In particular, the composition is effective against a variety of unwanted fungi that infect useful vegetable crops. The composition can be used against various Ascomycete and Basidiomycete fungi, including, for example, the following representative fungal species: On cucurbits: powdery mildew (Powdery mildew) Erysiphe cichoracearum , Sphaerotheca fuliginea) , ring spot (Mycosphaerella brassicicola) , blackleg (Mycosphaerella brassicicola ) (Plenodomus lingam) , anthracnose (Colletotrichum higginsianum) , Colletotrichum obiculare , Colletotrichum species , Cucurbits (Glomerella lagenarium) , gummy stem blight (Mycosphaerella melonis , Didymella bryoniae , Stagonosporopsis cucurbitacearum) ; Alternaria Alternaria leaf spot and blight (Alternaria cucumerina , Alternaria alternate f.sp. cucurbitae) , Alternaria (Alternaria alternate f.sp. cucurbitae) Alternaria species) , Cercospora leaf spot (Cercospora citrullina , Cercospora species ), Fusarium wilt ( Fusarium oxytocin) Fusarium oxysporum) , belly rot (Rhizoctonia solani) , Corynespora blight/target spot ( Corynespora blight/target spot) Corynespora cassiicola ) , scab ( Cladosporium cucumerinum ) , Verticillium wilt ( large Verticillium dahliae, Verticillium albo-atrum) , black root rot (Thielaviopsis basicola) , blue mold rot ( Penicillium species), charcoal rot (Macrophomina phaseolina ), and Craterrot (fruit) (Myrothecium roridum ); in On tomatoes: powdery mildew (Leveillula taurica) , Septoria leaf spot (Septoria lycopersici) , white mold ( rape core ) Sclerotinia sclerotiorum, Sclerotinia minor) , target spot (Corynespora cassiicola) , southern blight (Sclerotium rolfsii ) ) ), gray mold (Botrytis cinerea) , gray leaf spot (Stemphylium species), Fusarium wilt ), Fusarium crown and root rot (Fusarium oxysporum) , anhtracnose (Colletotrichum coccodes), black cotton Colletotrichum dematium, Colletotrichum gloeosporioides, Glomerella cingulate) , Alternaria stem canker and Alternaria stem canker and black mold) ( Alternaria alternata) , black root rot (Chalara elegans) , Cercospora leaf mold (Ce rcospora leaf mold) ( Cercospora fuligena) , charcoal rot (Maciophomina phaseolina ), corky root rot ( Acanthospora tomato ) (pyrenochaeta lycopersici) , Didymella stem rot (Didymella lycopersici) , early blight (Alternaria solani) , leaf leaf mold (passalora fulva, Mycovellosiella fulva) , phoma rot (Phoma destructive) , and acid sour rot (Geotrichum candidum) ; on leafy vegetables: Cercospora leaf spot (Cercospora longissima , Cercospora ) species ), gray mold/Botrytis rot (Botrytis cnerea) , Alternaria leaf spot and blight ( Alternaria sonchi , Alternaria species ), Powdery mildew (Erysiphe cichoracearum , Golovinomyces cichoracearum , Uncinula ) species ), rust (Puccinia dioicae) , Septoria leaf spot (Septoria lactucae, Septoria lactucae) (Septoria species ), southern blight (Sclerotium rolfsii) , basal rot (Phoma exigua) , Rhizoctonia bottom rot) (Rhizoctonia solan i) ), 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 ( alternating Alternaria alternata) , Cercospora leaf blotch (Cercospora concors) , charcoal rot (Macrophomina phaseolina) ), common rust (Puccinia pittieriana) , deforming rust ( Aecidium cantensis ), early blight ( Aecidium cantensis) Alternaria solani) , Fusarium dry rot and Fusarium wilt (Fusarium species), gangrene (P. Phoma exigua f.sp. foveata) , gray mold (Botrytis cinerea) , black blight or Phoma leaf spot ( Stagonosporopsis andigena , Phoma andigena var.andinai ), powdery mildew (Erysiphe cichoracearum) , Rhizoctonia canker and black Rhizoctonia canker and black scurf (Rhizoctonia solani) , Roselinia black rot (Rosellinia species ), scabies Septoria leaf spot (Septoria lycopersici var. malagutil) , silver scurf (Helminthosporium solani) , skin spot (Skin spot) ( Polyscytalum pustulans) , stem rot (Sclerotium rolfsii) , Thecaphora smut ( Potato smut (Thecaphora solani) , Ulocladium blight (Ulocladium atrum) , Verticillium wilt ( Verticillium wilt) albo-atrum) , and white mold (Sclerotinia sclerotiorum ); on peppers: southern blight (Sclerotium rolfsii) , powdery mildew ( Leveillula taurica ) , anthracnose (Colletotrichum capsici , Colletorichum acutatum , Colletorichum ) species ), Cercospora ( frogeye ) leaf spot (Cercospora capsici , Cercospora species ), charcoal rot (Cercospora capsici) (Macrophomina phaseolina ), damping-off and root rot (Rhizoctonia solani) , Fusarium stem rot (Fusarium solani ) (Fusarium solani) , Fusarium wilt (Fusarium oxysporum f.sp. capsici) , gray leaf spot (Stophyta ( Stemphyliu m) species ), gray mold (Botrytis cinerea) , Verticillium wilt (Verticillium albo-atrum) , and white mold (white mold) ( Sclerotinia sclerotiorum ); on cole crops: Alternarialeaf spot and blight ( Alternarialeaf spot and blight) Alternaria brassicicola), Alternaria sp. ), anthracnose (Colletotrichum sp. ), black leg (Leptosphaeria cruciferae ) maculans) , Phoma lingam) , Cercospora leaf spot (Cercopsora species ), Fusarium yellows and other diseases other diseases) (Fusarium species ), gray mold/ Botrytis blight (Botrytis cinerea) , powdery mildew (Erysiphepolygoni) ), Rhizoctoniarot and blight (Rhizoctonia solani) , ring spot (Mycosphaerella brassicicola) , Sclerotinia Sclerotinia rot (Sclerotinia species ), white leaf spot (Pseudocercosporella capsellae ).

Compound I has been found to have a significant fungicidal effect on phytopathogenic fungi of agriculturally useful vegetable crops. These diseases include Alternaria brassicicola , which causes black leaf spot of cabbage; Alternaria solani , which causes tomato early blight; Sclerotinia sclerotiorum of Sclerotinia rot of lettuce; Colletotrichum capsici which causes anthracnose of hot pepper; Colletotrichum capsici which causes cucumber powdery mildew ( Erysiphe cichoracearum of powdery mildew of cucumber; Mycovellosiella fulva that causes leaf mold of tomato; melons that cause gummy stem blight of watermelon Stagonosporopsis cucurbitacearum ; and Botrytis cinerea, which causes gray mold of broad bean, especially for agricultural use. Compound I is particularly effective for the use of agricultural crops and horticultural plants.

Compound I has a wide range of effects as fungicides. The exact amount of active material applied depends not only on the particular active material applied, but also on the specific effect desired, the fungal species to be controlled and its stage of growth, and the plant part or other product to be contacted with the compound. Therefore, Compound I and formulations containing Compound I may not be equally effective at similar concentrations or against the same species of fungi.

Compound I is effective when applied to plants in disease-inhibiting and phytologically acceptable amounts. The term "disease-inhibiting and phytologically acceptable amount" refers to a dose of a compound that kills or inhibits the plant disease it is intended to control, but is not significantly toxic to the plant. This dosage 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 will vary with the fungal disease to be controlled, the type of formulation employed, the method of application, the particular plant species, climatic conditions, and the like. Suitable application rates generally range from about 0.10 to about 4 pounds per acre (about 0.01 to 0.45 grams per square meter, g/m ² ).

Any range or desired value given herein may be extended or changed without losing the effect sought, as will be apparent to those skilled in the art from the understanding of the teachings herein.

Example:

Field evaluation of Alternaria brassicicola (ALTEBI) on cabbage :

A fungicidal treatment containing Compound I in a 5% EC formulation mixed with an adjuvant (Trycol, 50% w/w in 0.2% v/v) in a pail, sprayed Three times on head cabbage plants (BRSOL), the first application was made at the 10-12 LF cabbage growth stage. Subsequent applications were carried out at 7-day intervals, all at application rates of 50, 100 and 150 grams of active ingredient per hectare (gai/ha). The experimental plots were inoculated with the black leaf spot pathogen 2 days after the first application. This treatment was part of an experimental trial, which was a randomized complete block design with four replicates and a plot of approximately 2 x 1 meter in size, where Compound I was applied at 800 L/ha of water.

Disease severity was assessed as the percentage of diseased area in the bottom leaves of cabbage (6 plants randomly per plot). The area under the disease development curve (AUDPC) was calculated for each plot using the recorded severity dataset for three assessments of visual infection during the trial period 7 days after each application. Relative AUDPC (% control rate based on AUDPC), calculated as the percentage of untreated control group. The results are given in Table 1.

Field evaluation of Sclerotinia sclerotiorum (SCLESC) on lettuce:

A fungicidal treatment containing 5% of an EC formulation of Compound I, plus an adjuvant (Trycol, 50% w/w of 0.2% v/v), was sprayed on head lettuce plants ( LACSC) twice, the first application was at the heading stage 36 days after planting and the second application was 7 days later. Compound I formulations were applied at rates of 50, 100 and 150 grams of active ingredient per hectare (g ai/ha). The experimental plots were inoculated with the sclerotinia rot pathogen 2 days after the first application. This treatment was part of an experimental trial with a randomized complete block design with four replicates and a plot of approximately 2 x 1 meter in size, and the Compound I formulation was applied at 800 L/ha of water.

The percent disease infection was calculated by the formula of (length of stem damage)/(total stem length) x 100% for each plant (6 random plants per plot). Four sclerotinia rot infections were assessed 7 days after A's application (DAAA), plus 7, 14, 21 DAAB. Using the recorded visual infection dataset, the area under the disease development curve (AUPC) was calculated for each plot. Relative AUDPC (% control rate based on AUDPC), calculated as a percentage of untreated control. The results are given in Table 1.

Colletotrichum capsici (COLLCA) field assessment on hot peppers :

Evaluation of Compound I for COLLCA on peppers as both a protective and therapeutic agent was conducted in two separate field trials. In the 2-day protectant test, a fungicidal treatment containing 5% of an EC formulation of Compound I, plus an adjuvant (Trycol, 50% w/w of 0.2% v/v), The pepper plants (CPSAN) were sprayed three times with the first application at the flowering and fruiting period 43 days after planting, followed by 7-day intervals. Compound I formulations were applied at rates of 50, 100 and 150 grams of active ingredient per hectare (g ai/ha). The experimental plots were inoculated with anthracnose pathogen 2 days after the first application. This treatment was part of an experimental trial, which was a randomized complete block design with four replicates and a plot of approximately 2 x 1 meter in size, and the formulation of Compound I was applied at 1000 L/ha of water.

Disease severity was assessed as the percentage of fruit diseased area per plant (6 plants randomly per plot). Four anthracnose infections were assessed 7 days after administration of A (DAAA), 7DAAB, plus 7 and 14 DAAC. Using the recorded visual infection dataset, the area under the disease development curve (AUPC) was calculated for each plot. Relative AUDPC (% control rate based on AUDPC), calculated as the percentage of untreated control group. The results are given in Table 1.

In a 4-day therapeutic trial, a fungicidal treatment containing 5% of an EC formulation of Compound I, plus an adjuvant (Trycol, 50% w/w of 0.2% v/v), The pepper plants (CPSAN) were sprayed twice, the first application was 59 days after planting during the flowering and fruiting period, and the second application was 7 days later. Compound I formulations were applied at rates of 50, 100, 150 and 200 grams of active ingredient per hectare (gai/ha). The experimental plots were inoculated with the anthracnose pathogen (therapeutic agent) 4 days before the first application. This treatment was part of an experimental trial, which was a randomized complete block design with four replicates and a plot of approximately 2 x 1 meter in size, and the formulation of Compound I was applied at 1200 L/ha of water.

Disease severity was assessed as the percentage of fruit diseased area per plant (6 plants randomly per plot). Four days after administration of A (DAAA), plus 7, 14 and 21 DAAB, were assessed for four anthracnose infections. Using the recorded visual infection dataset, the area under the disease development curve (AUPC) was calculated for each plot. Relative AUDPC (% control rate based on AUDPC), calculated as the percentage of untreated control group. The results are given in Table 1.

Field assessment of Erysiphe cichoracearum (ERYSCI) on cucumber:

Evaluation of Compound I for ERYSCI on cucumber as a protective and therapeutic agent was performed in two separate field trials. In a two-day protective agent test (2DP), a fungicidal treatment containing 5% of an EC formulation of Compound I, plus an adjuvant (Trycol, 50% w/ of 0.2% v/v) w), sprayed twice on cucumber plants (CUMSA), the first application was in the fruiting period 41 days after planting and the next application was 7 days later. Compound I formulations were applied at rates of 50, 100 and 150 grams of active ingredient per hectare (g ai/ha). The experimental plots were inoculated with powdery mildew pathogen 2 days after the first application. This treatment was part of an experimental trial with a randomized complete block design with four replicates and a plot of approximately 2 x 1 m in size. The formulation of Compound I was applied at 1200 L/ha of water depending on the size of the seedlings.

Disease severity was assessed as the percentage of diseased area of cucumber leaves per plant (6 plants randomly per plot). Three cucumber powdery mildew infections were assessed 7 days after A (DAAA), and 7 and 14 DAAB. Using the recorded visual infection dataset, the area under the disease development curve (AUPC) was calculated for each plot. Relative AUDPC (% control rate based on AUDPC), calculated as the percentage of untreated control group. The results are given in Table 1.

In the therapeutic test, a fungicidal treatment containing 5% of an EC formulation of Compound I plus an adjuvant (Trycol, 50% w/w at 0.2% v/v) was sprayed on cucumber plants (CUMSA). ) twice, the first application was in the fruiting period 29 days after planting and the second application was 7 days later. The formulation application rates of Compound I were 50, 100 and 150 grams of active ingredient per hectare (g ai/ha). The experimental plots were inoculated with powdery mildew pathogens (therapeutic agents) 2 days before the first application. This treatment was part of an experimental trial with a randomized complete block design with four replicates and a plot size of approximately 2 x 1 m. The formulation of Compound I was applied at a water rate of 1200 L/ha, depending on the size of the seedlings.

Disease severity was assessed as the percentage of diseased area of cucumber leaves per plant (6 plants randomly per plot). Four times the disease severity of powdery mildew was assessed at 7 days after administration of A (DAAA), plus 7, 14 and 21 DAAB. Using the recorded visual infection dataset, the area under the disease development curve (AUPC) was calculated for each plot. Relative AUDPC (% control rate based on AUDPC), calculated as the percentage of untreated control group. The results are given in Table 1.

Field assessment of Alternaria solani (ALTESO) on tomatoes:

Evaluation of Compound I for ALTESO on tomato was carried out in two separate field experiments. In the first trial, a fungicidal treatment containing Compound I was used in a 5% EC and 10% SC formulation in a keg with an adjuvant (Agnique BP420, 0.3% v 50% w/w of /v) and sprayed on tomato plants (LYPES) approximately 60-70 cm in height at application rates of 100 and 200 grams of active ingredient per hectare (g ai/ha). The test was based on 5 foliar applications at 7 day intervals, with the early blight pathogen inoculation 2 days after the first application. This treatment was part of an experimental trial with a randomized complete block design with four replicates and a plot of approximately 1.5 x 4 meters in size. Compound I was applied at 1000 L/ha water with an AZO back sprayer using compressed air.

Disease severity was recorded as the percentage of diseased area on 20 randomly selected leaves and 20 fruits per plot. Percentage control was assessed as 6 assessments made between 0-35 days after the first application (DAA1). Using the recorded severity dataset, the area under the disease development curve (AUPC) was calculated for each plot. Relative AUDPC (% control rate based on AUDPC), calculated as the percentage of untreated control group. The results are given in Table 2.

In a replicate experiment, a fungicidal treatment containing Compound I was used in a 5% EC and 10% SC formulation with an adjuvant (Agnique BP420, 0.3% v 50% w/w of /v) and sprayed on tomato plants (LYPES, Taylor varietal) about 21 days after planting. The formulation application rates of Compound I were 100 and 200 grams of active ingredient per hectare (g ai/ha). The test was established with 6 foliar applications at 10 day intervals under the natural disease pressure of tomato early blight. This treatment was part of an experimental trial with a randomized complete block design with four replicates and a plot of approximately 2 x 4 meters in size. The Compound I formulation was applied with a water volume of 800 L/ha at a spray pressure of 300 kPa using a back ground sprayer (BKPCKENG, Solo 443; HCSOLID-Albutz ATR80 Orange nozzle). Disease severity (percent control) was recorded as visual leaf infection percentage for each plot and assessed 10 days after the last application. The results are given in Table 2.

Field evaluation of Mycovellosiella fulva (FULVFU) on tomatoes:

A 10% SC formulation of Compound I was mixed in a medicine keg with four different adjuvants: Agnique BP420 (50% w/w in 0.3% v/v); Trycol (in 0.1% v/v) of 50% w/w); Ethomeen T18H (50% w/w of 0.2% v/v); and Phase II (50% w/w of 0.2% v/v). Tomato plants were sprayed four times with a fungicidal treatment containing a formulation of Compound I (applied alone or with adjuvant), the first application being about 3 months after planting, followed by 7 to 10 days. interval for the next three applications. Compound I formulations were applied at rates of 50, 100, 150 and 200 grams of active ingredient per hectare (gai/ha). The experimental plots were inoculated with leaf mold pathogen (therapeutic agent) 7 days before the first application. This treatment was part of an experimental trial with a randomized complete block design with four replicates and a plot of approximately 2.5 x 1.4 meters in size. The formulation of Compound I was applied at a water level of 675 L/ha.

Disease severity was recorded as a visual percentage of diseased leaves (6 random plants per plot). Five tomato leaf mold infections were assessed 7 days after the first application (7 DAAA), 7 DAAB, 5 DAAC, followed by 7 and 12 DAAD. Using the recorded severity dataset, the area under the disease development curve (AUPC) was calculated for each plot. Relative AUDPC (% control rate based on AUDPC), calculated as the percentage of untreated control group. The results are given in Table 3.

Field assessment of Stagonosporopsis cucurbitacearum (DIDYBR) on watermelons:

A 10% SC formulation of Compound I was mixed in a medicine bucket with four different adjuvants: Agnique BP420 (50% w/w in 0.3% v/v); Trycol (in 0.1% v/v) of 50% w/w); Ethomeen T18H (50% w/w of 0.2% v/v); and Phase II (50% w/w of 0.2% v/v). A fungicidal treatment containing a formulation of Compound I (applied alone or with adjuvant) was sprayed on watermelon plants four times, the first application being about 2 months after planting, followed by 7 to 10 days. interval for the next three applications. Compound I formulations were applied at rates of 50, 100, 150 and 200 grams of active ingredient per hectare (gai/ha). Experimental plots were inoculated with gummy stem blight pathogen 2 days after the first application. This treatment was part of an experimental trial with a randomized complete block design with four replicates and a plot of approximately 2.5 x 1.4 meters in size. The formulation of Compound I was applied at a water level of 675 L/ha.

Disease severity was recorded as length of stem damage and percentage of leaf diseased area (random 3 plants per plot). Watermelon stemblight infection was assessed twice, first at 6 days after the first application (6 DAAA) and then at 19 DAAD. Using the recorded severity dataset, the area under the disease development curve (AUPC) was calculated for each plot. Relative AUDPC (% control rate based on AUDPC), calculated as the percentage of untreated control group. The results are given in Table 4.

Greenhouse Assessment of Botrytis cinerea (BOTRCI) on Broad Beans:

The technical grade material was dissolved in acetone and mixed with 9 volumes of water containing 100 ppm Triton X-100. The fungicide formulation was applied to the seedlings to overflow using an automatic compartment sprayer. Allow all sprayed plants to dry before proceeding further. Test plants were inoculated with Botrytis cinerea one day after application. When disease symptoms were fully present on untreated plants, the percentage of diseased area of the plants was assessed on a scale of 0 to 100 percent disease severity. Percent disease control was calculated using the ratio of disease severity on treated plants relative to untreated plants. The results are given in Table 5.

In each case in Tables 1 to 5, the rating scale based on the percentage of control by AUDPC is as follows:

Field assessment of Corynespora cassiicola (CORYCA) in tomatoes:

A fungicidal treatment containing Compound I in a SC formulation (built-in MSO) in a keg with an adjuvant (Agnique BP-420, 50% w/w in 0.2% v/v) , or mixed with Adsee C80W 80%) and sprayed on tomato plants (LYPES, Charger varietal) during the growth stage of BBCH64 (4th flowering) at application rates of 50, 75, 100, and 150 grams of active ingredient per hectare ( g ai/ha). One day after initial application, experimental plots were inoculated with target spot pathogens. This treatment was part of an experimental trial that was a randomized complete block (RCB) design with four replicates and a plot of approximately 6 x 25 feet (ft) size. Compound I was applied at 100 gallons per acre (gal/acre) of water at 200 psi using a trailed sprinkler (SCDISC D1 nozzle).

During the test period (1-20 days after application, DAA), disease severity (percentage of visually diseased foliage (leaves) on the entire plot) was assessed four times. Using the recorded severity dataset, the area under the disease development curve (AUPC) was calculated for each plot. Relative AUDPC (% control rate based on AUDPC), calculated as the percentage of untreated control group. The results are given in Table 6.

Field assessment of Colletotrichum coccodes (COLLCA) in tomatoes:

A fungicidal treatment containing a compound I formulation in a SC formulation (built-in MSO) in a pail with an adjuvant (Agnique BP-420, 50% w/ in 0.2% v/v) w, or mixed with Adsee C80W 80%) and sprayed on tomato plants (LYPES, Roma VS Saladette type variety) at vegetative growth stage 12 at application rates of 50, 75, 100 and 150 grams of active ingredient per hectare ( g ai/ha). The experimental plots were run with natural infection with the anthracnose pathogen and supplemented with additional inoculum approximately 1 day after the first application. This treatment was part of an experimental trial of a randomized complete block (RCB) design with four replicates and a plot of approximately 6.67 x 30 feet in size. Compound I was applied at 40 gal/acre of water at 38 psi using a back spray (carbon dioxide (CO ₂ ), 8004 VSFF nozzle).

During the test period (0-23 days after application 1), the percentage of leaf severity was assessed three times. Using the recorded leaf severity dataset, the area under the disease development curve (AUDPC) was calculated for each plot. Relative AUDPC (% control rate based on AUDPC), calculated as the percentage of untreated control group. The results are given in Table 7.

Claims (2)

A method of preventing and treating fungal diseases in vegetable crops at risk of disease selected from the group consisting of melons, tomatoes, leafy vegetables, potatoes, peppers and fava beans, comprising the steps of: contacting compound I or a composition comprising compound I at least a part of the plant and/or an area adjacent to the plant,

wherein the compound is effective against a phytopathogen, and wherein the fungal disease is selected from the group consisting of: blaclk leaf spot of cabbage (cabbage Alternaria brassicicola ), Sclerotinia rot of lettuce ( Sclerotinia sclerotiorum ), anthracnose of hot pepper (Sclerotinia sclerotiorum) ( Colletotrichum capsici ), leaf mold of tomato ( Mycovellosiella fulva ), gummy stem blight of watermelon ( Stagonosporopsis cucurbitacearum ) ), gray mold of broad bean ( Botrytis cinerea ), target spot of tomato ( Corynespora cassiicola ), and tomato anthracnose (anthracnose of tomato) ( Colletotrichum coccodes ). The method of claim 1, wherein the composition further comprises at least one additional agriculturally active ingredient selected from the group consisting of a pesticide, a herbicide, and a fungicide.