WO2018204432A1 - Utilisation d'un composé picolinamide acyclique comme fongicide pour lutter contre des champignons phytopathogènes dans des légumes - Google Patents

Utilisation d'un composé picolinamide acyclique comme fongicide pour lutter contre des champignons phytopathogènes dans des légumes Download PDF

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Publication number
WO2018204432A1
WO2018204432A1 PCT/US2018/030554 US2018030554W WO2018204432A1 WO 2018204432 A1 WO2018204432 A1 WO 2018204432A1 US 2018030554 W US2018030554 W US 2018030554W WO 2018204432 A1 WO2018204432 A1 WO 2018204432A1
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WIPO (PCT)
Prior art keywords
compound
tomato
herbicides
insecticides
plant
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PCT/US2018/030554
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English (en)
Inventor
Courtney Gallup
Valentino BOSCO
Chenglin Yao
Alisa Ye YU
Alejandro CALIXTO
Marsha Martin
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Dow Agrosciences Llc
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Priority to KR1020197035461A priority Critical patent/KR102555135B1/ko
Priority to IL270322A priority patent/IL270322B/en
Application filed by Dow Agrosciences Llc filed Critical Dow Agrosciences Llc
Priority to BR112019023042A priority patent/BR112019023042B8/pt
Priority to EP18793804.8A priority patent/EP3618621A4/fr
Priority to RU2019138680A priority patent/RU2769764C2/ru
Priority to AU2018261338A priority patent/AU2018261338B2/en
Priority to JP2019560356A priority patent/JP7189889B2/ja
Priority to US16/610,100 priority patent/US20200085047A1/en
Priority to CA3062162A priority patent/CA3062162A1/fr
Priority to MX2019013081A priority patent/MX2019013081A/es
Priority to CN201880042484.2A priority patent/CN111182791B/zh
Priority to CN202111426587.9A priority patent/CN114451413A/zh
Publication of WO2018204432A1 publication Critical patent/WO2018204432A1/fr
Priority to ZA2019/07338A priority patent/ZA201907338B/en
Priority to CONC2019/0013326A priority patent/CO2019013326A2/es
Priority to JP2022193699A priority patent/JP2023022261A/ja

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides

Definitions

  • This present disclosure is related to the field of the use of (S)-l,l-bis(4- fluorophenyl)propan-2-yl (3-acetoxy-4-methoxypicolinoyl)-L-alaninate to control fungal diseases in vegetables.
  • Fungicides are compounds, of natural or synthetic origin, which act to protect and cure plants against damage caused by agriculturally-relevant fungi. Generally, no single fungicide is useful in all situations. Consequently, research is ongoing to produce fungicides that may have better performance, are easier to use, and cost less.
  • the present disclosure relates to (S)-l,l-bis(4-fluorophenyl)propan-2-yl
  • Compound I (3-acetoxy-4-methoxypicolinoyl)-L-alaninate (compound I) and its use as a fungicide.
  • Compound I may offer protection against ascomycetes, basidiomycetes, and
  • One embodiment of the present disclosure includes a method of controlling a pathogen-induced disease in a plant that is at risk of being diseased from the pathogen comprising contacting the plant or an area adjacent to the plant with a composition including compound I.
  • Another embodiment of the present disclosure is a use of compound I for protection of a plant against attack by a phytopathogenic organism or the treatment of a plant infested by a phytopathogenic organism, comprising the application of compound I, or a composition including compound I to soil, a plant, a part of a plant, foliage, and/or seeds.
  • another embodiment of the present disclosure is a composition useful for protecting a plant against attack by a phytopathogenic organism and/or treatment of a plant infested by a phytopathogenic organism comprising compound I and a phytologically acceptable carrier material.
  • One exemplary embodiment of the present disclosure includes mixtures for controlling the growth of fungi, the mixture including compound I:
  • Compound I of the present disclosure may be applied by any of a variety of known techniques, either as compound I or as formulations comprising compound I.
  • compound I may be applied to the roots, stems, seeds, flowers, or foliage of plants for the control of various fungi, without damaging the commercial value of the plants.
  • Compound I may also be applied as a foliar spray, soil spray, soil incorporation, chemigation, soil drench, soil injection, or seed treatment.
  • the material may be applied in the form of any of the generally used formulation types, for example, as solutions, dusts, wettable powders, flowable concentrates, or emulsifiable concentrates.
  • compound I of the present disclosure is applied in the form of a formulation, including compound I with a phytologically acceptable carrier.
  • Concentrated formulations may be dispersed in water or other liquids for application, or formulations may be dust-like or granular, which may then be applied without further treatment.
  • the formulations can be prepared according to procedures that are conventional in the agricultural chemical art.
  • the present disclosure contemplates all vehicles by which compound I may be formulated for delivery and use as a fungicide.
  • formulations are applied as aqueous suspensions or emulsions.
  • Such suspensions or emulsions may be produced from water-soluble, water-suspendible, or emulsifiable formulations which are solids, usually known as wettable powders; or liquids, usually known as emulsifiable concentrates, aqueous suspensions, or suspension concentrates.
  • any material to which compound I may be added may be used, provided it yields the desired utility without significant interference with the activity of compound I as an antifungal agent.
  • Wettable powders which may be compacted to form water-dispersible granules, comprise an intimate mixture including compound I, an inert carrier and surfactants.
  • concentration of compound I in the wettable powder may be from about 10 percent to about 90 percent by weight based on the total weight of the wettable powder, more preferably about 25 weight percent to about 75 weight percent.
  • compound I may be compounded with any finely divided solid, such as prophyllite, talc, chalk, gypsum, Fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clays, diatomaceous earths, purified silicates or the like.
  • the finely divided carrier and surfactants are typically blended with compound I and milled.
  • Emulsifiable concentrates of compound I may comprise a convenient concentration, such as from about 10 weight percent to about 50 weight percent of compound I, in a suitable liquid, based on the total weight of the concentrate.
  • Compound I may be dissolved in an inert carrier, which is either a water-miscible solvent or a mixture of water-immiscible organic solvents, and emulsifiers.
  • the concentrates may be diluted with water and oil to form spray mixtures in the form of oil-in- water emulsions.
  • Useful organic solvents include aromatics, especially the high-boiling naphthalenic and olefinic portions of petroleum, such as heavy aromatic naphtha. Other organic solvents may also be used, for example, terpenic solvents, including rosin derivatives, aliphatic ketones, such as cyclohexanone, and complex alcohols, such as 2-ethoxyethanol.
  • Emulsifiers which may be advantageously employed herein may 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.
  • nonionic emulsifiers useful in preparing the emulsifiable concentrates include the polyalkylene glycol ethers and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as the ethoxylated alkyl phenols and carboxylic esters solubilized with the polyol or
  • Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts.
  • Anionic emulsifiers include the oil-soluble salts (e.g., calcium) of alkylaryl sulphonic acids, oil-soluble salts or sulfated polyglycol ethers and appropriate salts of phosphated polyglycol ether.
  • Representative organic liquids which may be employed in preparing the emulsifiable concentrates of compound I of the present invention are the aromatic liquids such as xylene, propyl benzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, particularly the dimethyl amides of fatty glycols and glycol derivatives such as the n-butyl ether, ethyl ether or methyl ether of diethylene glycol, and the methyl ether of triethylene glycol and the like.
  • aromatic liquids such as xylene, propyl benzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, particularly the dimethyl amides of fatty glycols and glycol derivatives such
  • Organic liquids include xylene, and propyl benzene fractions, with xylene being most preferred in some cases.
  • Surface-active dispersing agents are typically employed in liquid
  • formulations and in an amount of from 0.1 to 20 percent by weight based on the combined weight of the dispersing agent with compound I.
  • the formulations can also contain other compatible additives, for example, plant growth regulators and other biologically active compounds used in agriculture.
  • Aqueous suspensions including compound I may be dispersed in an aqueous vehicle at a concentration in the range 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 comprised of water and surfactants chosen from the same types discussed above.
  • Other components 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 may also be applied as a granular formulation, which is particularly useful for applications to the soil.
  • Granular formulations generally contain from about 0.5 to about 10 weight percent, based on the total weight of the granular formulation of compound I, dispersed in an inert carrier which consists entirely or in large part of coarsely divided inert material such as attapulgite, bentonite, diatomite, clay or a similar inexpensive substance.
  • Such formulations are usually prepared by dissolving compound I in a suitable solvent and applying it to a granular carrier which has been preformed to the appropriate particle size, in the range of from about 0.5 to about 3 mm.
  • a suitable solvent is a solvent in which compound I is substantially or completely soluble.
  • Such formulations may also be prepared by making a dough or paste of the carrier and compound I and solvent, and crushing and drying to obtain the desired granular particle.
  • Dusts containing compound I may be prepared by intimately mixing compound I in powdered form with a suitable dusty agricultural carrier, such as, for example, kaolin clay, ground volcanic rock, and the like. Dusts can suitably contain from about 1 to about 10 weight percent of compound I, based on the total weight of the dust.
  • a suitable dusty agricultural carrier such as, for example, kaolin clay, ground volcanic rock, and the like. Dusts can suitably contain from about 1 to about 10 weight percent of compound I, based on the total weight of the dust.
  • the formulations may additionally contain adjuvant surfactants to enhance deposition, wetting and penetration of compound I onto the target crop and organism.
  • adjuvant surfactants may optionally be employed as a component of the formulation or as a tank mix.
  • the amount of adjuvant surfactant will typically vary from 0.01 to 1.0 percent by volume, based on a spray-volume of water, preferably 0.05 to 0.5 volume percent.
  • Suitable adjuvant surfactants include, but are not limited to ethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols, salts of the esters or
  • formulations may also include oil-in-water emulsions such as those disclosed in U.S. Patent Application Serial No. 11/495,228, the disclosure of which is expressly incorporated by reference herein.
  • Aerial applications for vegetables utilize spray volumes preferably from 15 to 50 liters per hectare (L/ha) with standard surfactant, wetting, sticking, spreading or penetrating type additives such as non-ionic surfactants, organosilicones, or crop oil concentrates, preferably from 0.05 to 15 percent, based on a spray volume of water.
  • the formulations may optionally include combinations that contain other pesticidal compounds.
  • additional pesticidal compounds may be fungicides, insecticides, herbicides, nematocides, miticides, arthropodicides, bactericides, additives such as non-ionic surfactants, organosilicones, or crop oil concentrates, or combinations thereof that are compatible with the compounds of the present invention in the medium selected for application, and not antagonistic to the activity of the present compounds.
  • the other pesticidal compound is employed as a supplemental toxicant for the same or for a different pesticidal use.
  • Compound I and the pesticidal compound in the combination can generally be present in a weight ratio of from 1: 100 to 100: 1.
  • Compound I of the present disclosure may also be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof.
  • Compound I of the present disclosure is often applied in conjunction with one or more other fungicides to control a wider variety of undesirable diseases.
  • the presently claimed compound I may be formulated with the other fungicide(s), tank-mixed with the other fungicide(s) or applied sequentially with the other fungicide(s).
  • Such other fungicides may include 2-(thiocyanatomethylthio)- benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, ametoctradin, amisulbrom, antimycin, Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis, Bacillus subtilis strain QST713, benalaxyl, benomyl, benthiavalicarb-isopropyl, benzylaminobenzene- sulfonate (BABS) salt, bicarbonates, biphenyl, bismerthiazol, bitertanol, bixafen, blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole, bupirimate, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, carvone, chlazafenone, chloroneb, chlor
  • metconazole methasulfocarb, methyl iodide, methyl isothiocyanate, metiram, metominostrobin, 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, phenylmercury acetate, phosphonic acid, phthalide, picoxystrobin, polyoxin B, polyoxins, polyoxorim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymid
  • compound I of the present invention may be combined with other pesticides, including insecticides, nematicides, miticides, arthropodicides, bactericides or combinations thereof that are compatible with compound I of the present invention in the medium selected for application, and not antagonistic to the activity of compound I, to form pesticidal mixtures and synergistic mixtures thereof.
  • Compound I of the present disclosure may be applied in conjunction with one or more other pesticides to control a wider variety of undesirable pests.
  • the presently claimed compound I may be formulated with the other pesticide(s), tank mixed with the other pesticide(s) or applied sequentially with the other pesticide(s).
  • Typical insecticides include, but are not limited to: antibiotic insecticides such as allosamidin and thuringiensin; macrocyclic lactone insecticides such as spinosad and spinetoram; avermectin insecticides such as abamectin, doramectin, emamectin, eprinomectin, ivermectin and selamectin; milbemycin insecticides such as lepimectin, milbemectin, milbemycin oxime and moxidectin; carbamate insecticides such as bendiocarb and carbaryl; benzofuranyl methylcarbamate insecticides such as benfuracarb, carbofuran, carbosulfan, decarbofuran and furathiocarb; dimethylcarbamate insecticides dimitan, dimetilan, hyquincarb and pirimicarb; oxime carbamate insecticides such as al
  • moulting hormone agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide; moulting hormones such as a-ecdysone and ecdysterone; moulting inhibitors such as diofenolan; precocenes such as precocene I, precocene II and precocene III; unclassified insect growth regulators such as dicyclanil; nereistoxin analogue insecticides such as bensultap, cartap, thiocyclam and thiosultap;
  • pyridylpyrazole insecticides such as tyclopyrazoflor; nicotinoid insecticides such as flonicamid; 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, camphechlor, DDT, pp'-DDT, ethyl-DDD, HCH, gamma-HCH, lindane, methoxychlor, pentachlorophenol and TDE
  • cyclodiene insecticides such as aldrin, bromocyclen, chlorbicyclen, chlordane, chlordecone, dieldrin, dilor, endosulfan, alpha-endosulfan, endrin, HEOD, heptachlor, HHDN, isobenzan, isodrin, kelevan and mirex;
  • organophosphate insecticides such as bromfenvinfos, chlorfenvinphos, crotoxyphos, dichlorvos, dicrotophos, dimethylvinphos, fospirate, heptenophos, methocrotophos, mevinphos, monocrotophos, naled, naftalofos, phosphamidon, propaphos, TEPP and tetrachlorvinphos; organothiophosphate insecticides such as dioxabenzofos, fosmethilan and phenthoate; aliphatic organothiophosphate insecticides such as acethion, amiton, cadusafos, chlorethoxyfos, chlormephos, demephion, demephion-O, demephion-S, demeton, demeton-O, demeton-S, demeton-methyl, demeton-O-methyl, demeton-S- methyl, demeton-
  • organothiophosphate insecticides such as azamethiphos, coumaphos, coumithoate, dioxathion, endothion, menazon, morphothion, phosalone, pyraclofos, pyridaphenthion and quinothion; henzothiopyran organothiophosphate insecticides such as dithicrofos and thicrofos; benzotriazine organothiophosphate insecticides such as azinphos-ethyl and azinphos -methyl; isoindole organothiophosphate insecticides such as dialifos and phosmet; isoxazole organothiophosphate insecticides such as isoxathion and zolaprofos; pyrazolopyrimidine organothiophosphate insecticides such as chlorprazophos and pyrazophos; pyridine organothiophosphate insecticides such as chlorpyrif
  • phenylphosphonothioate insecticides such as cyanofenphos, EPN and leptophos;
  • phosphor amidate insecticides such as crufomate, fenamiphos, fosthietan, mephosfolan, phosfolan and pirimetaphos; phosphoramidothioate insecticides such as acephate, isocarbophos, isofenphos, isofenphos-methyl, methamidophos and propetamphos;
  • phosphorodiamide insecticides such as dimefox, mazidox, mipafox and schradan;
  • oxadiazine insecticides such as indoxacarb
  • oxadiazoline insecticides such as
  • phthalimide insecticides such as dialifos, 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, chloroprallethrin, cyclethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethr
  • compound I of the present invention may be combined with herbicides that are compatible with compound I of the present invention in the medium selected for application, and not antagonistic to the activity of compound I to form pesticidal mixtures and synergistic mixtures thereof.
  • the fungicidal compound I of the present disclosure may be applied in conjunction with one or more herbicides to control a wide variety of undesirable plants.
  • the presently claimed compound I may be formulated with the herbicide(s), tank mixed with the herbicide(s) or applied sequentially with the herbicide(s).
  • Typical herbicides include, but are not limited to: amide herbicides such as allidochlor, beflubutamid, benzadox, benzipram, bromobutide, cafenstrole, CDEA, cyprazole, dimethenamid, dimethenamid-P, diphenamid, epronaz, etnipromid, fentrazamide, flupoxam, fomesafen, halosafen, isocarbamid, isoxaben, napropamide, naptalam, pethoxamid, propyzamide, quinonamid, tebutam and tiafenacil; anilide herbicides such as chloranocryl, cisanilide, clomeprop, cypromid, diflufenican, etobenzanid, fenasulam, flufenacet, flufenican, mefenacet, mefluidide, metam
  • chloroacetanilide herbicides such as acetochlor, alachlor, butachlor, butenachlor, delachlor, diethatyl, dimethachlor, metazachlor, metolachlor, S-metolachlor, pretilachlor, propachlor, propisochlor, prynachlor, terbuchlor, thenylchlor and xylachlor; sulfonanilide herbicides such as benzofluor, perfluidone, pyrimisulfan and profluazol; sulfonamide herbicides such as asulam, 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; pyrimidinyloxybenzoic acid herbicides such as bispyribac and pyrimin
  • quinolinecarboxylic acid herbicides such as quinclorac and quinmerac
  • arsenical herbicides such as cacodylic acid, CMA, DSMA, hexaflurate, MAA, MAMA, MSMA, potassium arsenite and sodium arsenite
  • benzoylcyclohexanedione herbicides such as fenquinotrione, lancotrione, mesotrione, sulcotrione, tefuryltrione and tembotrione;
  • benzofuranyl alkylsulfonate herbicides such as benfuresate and ethofumesate
  • benzothiazole herbicides such as benzazolin
  • carbamate herbicides such as asulam, carboxazole chlorprocarb, dichlormate, fenasulam, karbutilate and terbucarb
  • carbanilate herbicides such as barban, BCPC, carbasulam, carbetamide, CEPC, chlorbufam, chlorpropham, CPPC, desmedipham, phenisopham, phenmedipham, phenmedipham- ethyl, propham and swep
  • cyclohexene oxime herbicides such as alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim and tralkoxydim
  • methoxytriazine herbicides such as atraton, methometon, prometon, secbumeton, simeton and terbumeton; methylthiotriazine herbicides such as ametryn, aziprotryne, cyanatryn, desmetryn, dimethametryn, methoprotryne, prometryn, simetryn and terbutryn; triazinone herbicides such as ametridione, amibuzin, hexazinone, isomethiozin, metamitron, metribuzin, and trifludimoxazin; triazole herbicides such as amitrole, cafenstrole, epronaz and flupoxam; triazolone herbicides such as amicarbazone, bencarbazone, carfentrazone, flucarbazone, ipfencarbazone, propoxycarbazone, sulfentrazone and thi
  • methabenzthiazuron, monisouron and noruron phenylurea herbicides such as anisuron, buturon, chlorbromuron, chloreturon, chlorotoluron, chloroxuron, daimuron,
  • metazosulfuron metazosulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron,
  • propyrisulfuron pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron and
  • trifloxysulfuron triazinylsulfonylurea herbicides such as chlorsulfuron, cinosulfuron, ethametsulfuron, iodosulfuron, iofensulfuron, metsulfuron, prosulfuron, thifensulfuron, triasulfuron, tribenuron, triflusulfuron and tritosulfuron; thiadiazolylurea herbicides such as buthiuron, ethidimuron, tebuthiuron, thiazafluron and thidiazuron; and unclassified herbicides such as acrolein, allyl alcohol, aminocyclopyrachlor, azafenidin, bentazone, benzobicyclon, bicyclopyrone, buthidazole, calcium cyanamide, cambendichlor, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, cin
  • Compound I of the present invention can also comprise or may be applied together and/or sequentially with further active compounds.
  • These further compounds can be plant health stimulants, such as organic compounds, inorganic fertilizers, or micronutrient donors or other preparations that influence plant growth, such as inoculants.
  • Compound I can also comprise or may be applied together and/or sequentially with other biological organisms, such as, but not limited to the group consisting of Bacillus strains, for example Bacillus subtilis var. amyloliquefaciens FZB24 (TAEGRP ® ) and Bacillus amyloliquefaciens FZB42 (RHIZO VITAL ® ) , VotiVoTM Bacillus firmus, ClarivaTM (Pasteuria nishizawae), Bacillus thuringiensis, Trichoderma spp., and/or mutants and metabolites of the respective strains that exhibit activity against insects, mites, nematodaes, and/or phytopathogens.
  • Bacillus strains for example Bacillus subtilis var. amyloliquefaciens FZB24 (TAEGRP ® ) and Bacillus amyloliquefaciens FZB42 (RHIZO VITAL ® )
  • One embodiment of the present disclosure is a method for the control or prevention of fungal attack.
  • This method comprises applying to the soil, plant, roots, foliage, seed or locus of the fungus, or to a locus in which the infestation is to be prevented (for example applying to cereal or grape plants), a fungicidal effective amount of compound I.
  • Compound I is suitable for treatment of various plants at fungicidal levels, while exhibiting low phy to toxicity. Compound I may be useful both in a protectant and/or an eradicant fashion.
  • the compound of Formula I has been found to have significant fungicidal effects particularly for agricultural use.
  • the compound of Formula I is particularly effective for use with agricultural crops and horticultural plants. Additional benefits may include, but are not limited to, improving the health of a plant; improving the yield of a plant (e.g. increased biomass and/or increased content of valuable ingredients);
  • improving the vigor of a plant e.g. improved plant growth and/or greener leaves
  • the composition is effective in controlling a variety of undesirable fungi that infect useful vegetable crops.
  • the composition maybe used against a variety of Ascomycete and Basidiomycete fungi, including, for example, the following representative fungi species:
  • Cercospora spp. gray mold/Botrytis rot ⁇ Botrytis cinerea), Alternaria leaf spot and blight ⁇ Alternaria sonchi, Alternaria spp.), powdery mildew ⁇ Erysiphe dehor acearum, 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 drop
  • Alternaria spp. 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
  • Compound I has been found to have significant fungicidal effects 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, which causes Sclerotinia rot of lettuce; Colletotrichum capsici, which causes anthracnose of hot pepper; Erysiphe dehor acearum, which causes powdery mildew of cucumber; Mycovellosiella fulva, which causes leaf mold of tomato; Stagonosporopsis cucurbitacearum, which causes gummy stem blight of watermelon; and Botrytis cinerea, which causes broad bean grey mold, particularly for agricultural use. Compound I is particularly effective for use with agricultural crops and horticultural plants.
  • Compound I has a broad range of efficacy as a fungicide.
  • the exact amount of the active material to be applied is dependent not only on the specific active material being applied, but also on the particular action desired, the fungal species to be controlled, and the stage of growth thereof, as well as the part of the plant or other product to be contacted with the compound.
  • compound I, and formulations containing the same may not be equally effective at similar concentrations or against the same fungal species.
  • Compound I is effective in use with plants in a disease-inhibiting and phytologically acceptable amount.
  • the term "disease-inhibiting and phytologically acceptable amount” refers to an amount of a compound that kills or inhibits the plant disease for which control is desired, but is not significantly toxic to the plant. This amount will generally be from about 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm being preferred.
  • the exact concentration of compound required varies with the fungal disease to be controlled, the type of formulation employed, the method of application, the particular plant species, climate conditions, and the like.
  • a suitable application rate is typically in the range from about 0.10 to about 4 pounds/acre (about 0.01 to 0.45 grams per square meter, g/m 2 ).
  • Formulations of compound I were applied at rates of 50, 100, and 150 grams of active ingredient per hectare (g ai/ha).
  • the experimental plots were inoculated with sclerotinia rot pathogen 2 days after the first application.
  • the treatment was part of an experimental trial designed as a randomized complete block with four replications and a plot of approximately 2 x 1 m, with formulations of compound I being applied at water volume of 800 L/ha.
  • a fungicidal treatment containing a 5% EC formulation of compound I plus an adjuvant (Trycol, 50% w/w at 0.2% v/v) was sprayed on hot pepper plants (CPSAN) twice, the first application at the flowering and fruiting stage 59 days after planting, with the second application after 7 days.
  • Formulations of compound I were applied at rates of 50, 100, 150 and 200 grams of active ingredient per hectare (g ai/ha).
  • the experimental plots were inoculated with the anthracnose pathogen 4 days before the first application (curative).
  • the treatment was part of an experimental trial designed as a randomized complete block with four replications and a plot of approximately 2 x 1 m, with formulations of compound I being applied at water volume of 1200 L/ha.
  • a fungicidal treatment containing a 5% EC formulation of compound I plus an adjuvant was sprayed on cucumber plants (CUMSA) twice, the first application at the fruiting stage 29 days after planting, with the second application after 7 days.
  • Formulations of compound I 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 powdery mildew pathogen 2 days before the first application (curative).
  • the treatment was part of an experimental trial designed as a randomized complete block with four replications and a plot of approximately 2 x 1 m, with formulations of compound I being applied at water volume of 1200 L/ha based on seedling sizes.
  • Formulations of compound I were applied at water volume of 800 L/ha, using a backpack plot sprayer (BKPCKENG, Solo 443; HCSOLID - Albutz ATR80 Orange Nozzle) and pressurized at 300 kPa. Disease severity (percent control) was recorded as percent visual leaf infection per plot and was assessed at 10 days after the last application. Results are given in Table 2.
  • a 10% SC formulation of compound I was tanked mixed with four different adjuvants: Agnique BP420 (50% w/w at 0.3% v/v); Trycol (50% w/w at 0.1% v/v);
  • Ethomeen T18H (50% w/w at 0.2% v/v); and Phase ⁇ (50% w/w at 0.2% v/v).
  • Formulations of compound I were applied at rates of 50, 100, 150 and 200 grams of active ingredient per hectare (g ai/ha).
  • the experimental plots were inoculated with the leaf mold pathogen 7 days before the first application (curative).
  • the treatment was part of an experimental trial designed as a randomized complete block with four replications and a plot of approximately 2.5 x 1.4 m.
  • Formulations of compound I were applied at water volume of 675 L/ha.
  • DIDYBR Stagonosporopsis cucurbitacearum
  • Ethomeen T18H (50% w/w at 0.2% v/v); and Phase ⁇ (50% w/w at 0.2% v/v).
  • Formulations of compound I were applied at rates of 50, 100, 150 and 200 grams of active ingredient per hectare (g ai/ha).
  • the experimental plots were inoculated with the gummy stem blight pathogen 2 days after the first application.
  • the treatment was part of an experimental trial designed as a randomized complete block with four replications and a plot of approximately 2.5 x 1.4 m.
  • Formulations of compound I were applied at water volume of 675 L/ha.
  • AUDPC is as follows:
  • Table 1 Percent Control by Compound I a on Fungal Diseases of Vegetables Based on Area Under Disease Progression Curve (AUDPC) in Protectant and Curative Tests.
  • Table 2 Efficacy of Compound I a against Early Blight (ALTESO, Alternariasolani) on Leaves and Fruits of Tomato in EC and SC Formulations.
  • Table 4 Efficacy a of Compound I against Watermelon Gummy Stem Blight (DIDYBR, Stagonosporopsis cucurbitacearum) in a 10% SC Formulation with or without
  • a fungicidal treatment containing Compound I applied in an SC formulation (MSO built-in) and tank mixed with an adjuvant (Agnique BP-420, 50% w/w at 0.2% v/v or Adsee C80W 80%), was sprayed on tomato plants (LYPES, Charger variety) at growth stage BBCH64 (4 th flower open) at rates of 50, 75, 100, and 150 grams of active ingredient per hectare (g ai/ha).
  • the experimental plots were inoculated with the target spot pathogen one day after initial application.
  • the treatment was part of an experimental trial designed as a randomized complete block (RCB) with four replications and a plot of approximately 6 x 25 feet (ft).
  • Compound I was applied at water volume of 100 gallons per acre (gal/acre), using a tractor sprayer (SCDISC Dl Nozzles) and pressurized at 200 psi.
  • a fungicidal treatment containing Compound I applied in an SC formulation (MSO built-in) and tank mixed with an adjuvant (Agnique BP-420, 50% w/w at 0.2% v/v or Adsee C80W 80%), was sprayed on tomato plants (LYPES, Roma VS Saladette type variety) at growth stage 12 in vegetative growth at rates of 50, 75, 100, and 150 grams of active ingredient per hectare (g ai/ha).
  • the experimental plots were run with natural infestation of the anthracnose pathogen and supplemented with additional inoculum about one day after the 1 st application.
  • the treatment was part of an experimental trial designed as a randomized complete block (RCB) with four replications and a plot of approximately 6.67 x 30 ft.
  • Compound I was applied at water volume of 40 gal/acre, using a backpack sprayer (carbon dioxide (C0 2 ), 8004VS FF nozzles) and pressurized at 38 psi.
  • Table 7 Formulation Comparison of Compound I with MSO or Tank- Mixed with Agnique BP-420 of Calculated Percent Control of Anthracnose of Tomato (COLLCA, Colletotrichum coccodes)

Abstract

La présente invention concerne le domaine des produits agrochimiques, notamment le composé (I) et son utilisation pour lutter contre des maladies fongiques dans des cultures légumières utiles en agriculture.
PCT/US2018/030554 2017-05-02 2018-05-02 Utilisation d'un composé picolinamide acyclique comme fongicide pour lutter contre des champignons phytopathogènes dans des légumes WO2018204432A1 (fr)

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CA3062162A CA3062162A1 (fr) 2017-05-02 2018-05-02 Utilisation d'un compose picolinamide acyclique comme fongicide pour lutter contre des champignons phytopathogenes dans des legumes
US16/610,100 US20200085047A1 (en) 2017-05-02 2018-05-02 Use of an Acyclic Picolinamide Compound as a Fungicide for Control of Phytopathogenic Fungi in Vegetables
BR112019023042A BR112019023042B8 (pt) 2017-05-02 2018-05-02 Método para controle de doenças fúngicas em culturas vegetais
IL270322A IL270322B (en) 2017-05-02 2018-05-02 Use of an acyclic picolinamide compound as a fungicide to control phytopathogenic fungi in vegetables
RU2019138680A RU2769764C2 (ru) 2017-05-02 2018-05-02 Применение ациклического пиколинамидного соединения в качестве фунгицида для контроля фитопатогенных грибов в овощных культурах
AU2018261338A AU2018261338B2 (en) 2017-05-02 2018-05-02 Use of an acyclic picolinamide compound as a fungicide for control of phytopathogenic fungi in vegetables
MX2019013081A MX2019013081A (es) 2017-05-02 2018-05-02 Uso de un compuesto de picolinamida aciclica como un fungicida para el control de hongos fitopatogenos en verduras.
KR1020197035461A KR102555135B1 (ko) 2017-05-02 2018-05-02 채소류에서의 식물병원 진균 방제를 위한 살진균제로서의 비고리형 피콜린아미드 화합물의 용도
EP18793804.8A EP3618621A4 (fr) 2017-05-02 2018-05-02 Utilisation d'un composé picolinamide acyclique comme fongicide pour lutter contre des champignons phytopathogènes dans des légumes
JP2019560356A JP7189889B2 (ja) 2017-05-02 2018-05-02 野菜における植物病原性真菌を制御するための殺真菌剤としての非環式ピコリンアミド化合物の使用
CN201880042484.2A CN111182791B (zh) 2017-05-02 2018-05-02 无环吡啶酰胺化合物作为用于防治蔬菜中的植物病原性真菌的杀真菌剂的用途
CN202111426587.9A CN114451413A (zh) 2017-05-02 2018-05-02 无环吡啶酰胺化合物作为用于防治蔬菜中的植物病原性真菌的杀真菌剂的用途
ZA2019/07338A ZA201907338B (en) 2017-05-02 2019-11-05 Use of an acyclic picolinamide compound as a fungicide for control of phytopathogenic fungi in vegetables
CONC2019/0013326A CO2019013326A2 (es) 2017-05-02 2019-11-27 Uso de un compuesto de picolinamida acíclica como fungicida para el control de hongos fitopatógenos en verduras
JP2022193699A JP2023022261A (ja) 2017-05-02 2022-12-02 野菜における植物病原性真菌を制御するための殺真菌剤としての非環式ピコリンアミド化合物の使用

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TW201902357A (zh) * 2017-05-02 2019-01-16 美商陶氏農業科學公司 用作種子處理之無環吡啶醯胺
TWI801381B (zh) * 2017-05-02 2023-05-11 美商科迪華農業科技有限責任公司 非環狀吡啶醯胺化合物作為殺真菌劑以防治行栽作物中具植物病原性的真菌之用途

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RU2019138680A (ru) 2021-06-03
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IL270322B (en) 2022-06-01
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TWI774762B (zh) 2022-08-21
CL2019003111A1 (es) 2020-02-21
CN111182791B (zh) 2021-12-21
BR112019023042A2 (pt) 2020-06-02
JP7189889B2 (ja) 2022-12-14
TW201842850A (zh) 2018-12-16
KR20200011948A (ko) 2020-02-04
CO2019013326A2 (es) 2020-01-17
EP3618621A1 (fr) 2020-03-11
CN114451413A (zh) 2022-05-10
RU2019138680A3 (fr) 2021-10-01
BR112019023042B1 (pt) 2023-12-26
ECSP19085003A (es) 2019-12-27
AR111745A1 (es) 2019-08-14
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JP2020518634A (ja) 2020-06-25
KR102555135B1 (ko) 2023-07-13
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