WO2016007525A1 - Picolinamides macrocycliques utilisés pour le traitement des semences - Google Patents

Picolinamides macrocycliques utilisés pour le traitement des semences Download PDF

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Publication number
WO2016007525A1
WO2016007525A1 PCT/US2015/039401 US2015039401W WO2016007525A1 WO 2016007525 A1 WO2016007525 A1 WO 2016007525A1 US 2015039401 W US2015039401 W US 2015039401W WO 2016007525 A1 WO2016007525 A1 WO 2016007525A1
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WIPO (PCT)
Prior art keywords
plant
compound
formula
seed
treated
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PCT/US2015/039401
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English (en)
Inventor
Carla J.R. Klittich
Chenglin Yao
Fangzheng LI
Kevin G. Meyer
Benjamin Nugent
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Dow Agrosciences Llc
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Publication of WO2016007525A1 publication Critical patent/WO2016007525A1/fr

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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present disclosure relates to methods of controlling phytopathogenic fungi by treating seeds with a novel seed treatment fungicide.
  • seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed imbibition (soaking), seed foaming (i.e. covering in foam) and seed pelleting, and refers preferably to the application of a fungicidally active compound(s) directly to the seeds themselves, prior to planting, and/or in their immediate vicinity during planting.
  • An embodiment of the present disclosure may include a method for the control or prevention of fungal attack on a plant, the method including the steps of applying a fungicidally effective amount of a compound of Formula I to a seed adapted to produce the plant.
  • Some aspects of the invention include methods of treating a plant seed to produce a plant resistant to fungal attack, compiring the step of treating a plant seed is treated with a compound of Formula I.
  • X is O or CH 2 ;
  • Ri is CH 2 CH(CH 3 ) 2 , or Ph;
  • R 2 is CH 2 Ph, OCH 2 CH(CH 3 ); or OCH 2 CH(CH 3 ) 2 ;
  • R 3 is CH 2 OC(0)CH 3 or C(0)CH 3 .
  • the compound of Formula I used in the method is at least one compound selected from the group consisting of compounds: 1 wherein: X is O, Rl is CH2CH(CH3)2; R2 is CH2Ph; and R3 is CH20C(0)CH3; 2 wherein: X is CH2, Rl is Ph; R2 is OCH2CH2CH3; and R3 is C(0)CH3; 3 wherein: X is O, Rl is CH2CH(CH3)2; R2 is
  • OCH2CH(CH3)2 and R3 is CH20C(0)CH3; and 4 wherein: X is CH2, Rl is CH2CH(CH3)2; R2 is CH2Ph; and R3 is CH20C(0)CH3.
  • the compound of Formula I is applied at a rate from about
  • te fungal pathogen is at least pathogen selected from the group consisting of the causal agent of wheat leaf blotch (Septoria tritici), wheat glume blotch (Leptosphaeria nodorum), wheat brown rust (Puccinia triticina), and wheat powdery mildew (Blumeria graminis f. sp. tritici).
  • Some aspects of the invention include plant seeds adapted to produce a plant resistant to fungal and insect attack, wherein the plant seed is treated with a compound of Formula I and one or more insecticides.
  • the plant seed is adapted to produce a plant resistant to fungal attack, wherein the plant seed is treated with a compound of Formula I and one or more fungicides.
  • the plant seed is adapted to produce a plant resistant to fungal attack and eradicate undesirable vegetation, wherein the plant seed is treated with a compound of Formula I and one or more herbicides.
  • the plant seed is adapted to produce plants resistant to fungal attack, wherein the plant seed is treated with a compound of Formula I and one or more additional plant health stimulators selected from the group consisting of organic compounds, inorganic fertilizers or micronutrient donors and inoculants.
  • Some aspects of the inventin include methods of treating a plant seedling to produce a plant resistant to fungal attack, wherein the plant seedling is treated with a compound of Formula I:
  • X is O or CH 2 ;
  • Ri is CH 2 CH(CH 3 ) 2 , or Ph;
  • R 2 is CH 2 Ph, OCH 2 CH(CH 3 ); or OCH 2 CH(CH 3 ) 2 ;
  • R 3 is CH 2 OC(0)CH 3 or C(0)CH 3 .
  • the compound of Formula I used in the method is at least one compound selected from the group of compounds consisting of: 1 wherein: X is O, Ri is CH 2 CH(CH 3 ) 2 ; R 2 is CH 2 Ph; and R 3 is CH 2 OC(0)CH 3 ; 2 wherein: X is CH 2 , Rj is Ph; R 2 is OCH 2 CH 2 CH 3 ; and R 3 is C(0)CH 3 ; 3 wherein: X is O, Ri is CH 2 CH(CH 3 ) 2 ; R 2 is
  • OCH 2 CH(CH 3 ) 2 and R 3 is CH 2 OC(0)CH 3 ; and 4 wherein: X is CH 2 , Ri is CH 2 CH(CH 3 ) 2 ; R 2 is CH 2 Ph; and R 3 is CH 2 OC(0)CH 3 .
  • the seedling being treated is a seedling of wheat
  • the fungal pathogen is selected from the group consisting of the causal agent of wheat leaf blotch (Septoria tritici), wheat glume blotch
  • Some embodiments include treating a plant seedling adapted to produce a plant resistant to fungal and insect attack, wherein the plant seed is treated with a compound of Formula I and one or more insecticides.
  • the plant seedling is adapted to produce a plant resistant to fungal attack, wherein the plant seed is treated with a compound of Formula I and one or more fungicides.
  • Some embodiments include a plant seedling adapted to produce a plant resistant to fungal attack and eradicate undesirable vegetation, wherein the plant seed is treated with a compound of Formula I and one or more herbicides.
  • Some embodiments include plant seedlings adapted to produce plants resistant to fungal attack, wherein the plant seed is treated with a compound of Formula I and one or more additional plant health stimulators selected from the group consisting of organic compounds, inorganic fertilizers or micronutrient donors and inoculants.
  • the plant seedling is adapted to produce a plant resistant to fungal attack, wherein the plant seedling is treated with a compound of Formula I.
  • Some aspects include a method method of protecting a plant from fungal attack comprising the application of at least one compound of Formula I, as a liquid or solid
  • Some aspects of the present disclosure is a method for controlling
  • phytopathogenic fungi in and/or on a plant wherein the seeds, from which the plant is expected to grow, before sowing and/or after pregermination, are treated with a compound of Formula I.
  • Seed treatment can independently include application of a compound of Formula I directly to the seed as a coating or application to the seed environment as a liquid or solid formulation. Additionally, a compound of Formula I may be applied as a liquid or solid formulation to a seedling environment.
  • a seed is broadly interpreted to include anything that can be sown and can potentially be set in place (soil) to grow a crop.
  • the term "seed” embraces seeds and plant propagules of all kinds including, but not limited to, true seeds, seed pieces, grains, suckers, corms, bulbs, fruit, tubers, cuttings, cut shoots and similar forms, and preferably means a true seed.
  • a seedling is a germinated seed.
  • a seedling environment is the soil or other growth medium surrounding the seedling.
  • Formula I can be formulated for delivery and use as a seed treatment fungicide
  • Conventional seed treatment formulations include for example flowable concentrates, solutions, powders for dry treatment, water dispersible powders for slurry treatment, water-soluble powders and emulsion and gel formulations. These formulations can be applied diluted or undiluted.
  • formulations are applied following dilution of the concentrated formulation with water as aqueous solutions, suspensions or emulsions, or combinations thereof.
  • solutions, suspensions or emulsions may be produced from water-soluble, water- suspendible, or emulsifiable formulations or combinations thereof, which are solids, including and usually known as wettable powders or water dispersible granules; or liquids including and usually known as emulsifiable concentrates, aqueous suspensions or suspension concentrates, and aqueous emulsions or emulsions in water, or mixtures thereof such as suspension-emulsions.
  • any material to which this composition can be added may be used, provided it yields the desired utility without significant interference with the desired activity of the pesticidally active ingredients as pesticidal agents, improves residual lifetime, or decreases the effective concentration required to achieve the pesticidal effect.
  • Wettable powders which may be compacted to form water dispersible granules, comprise an intimate mixture of one or more of the pesticidally active ingredients, an inert carrier and surfactants.
  • concentration of the pesticidally active ingredient in the wettable powder is usually 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.
  • the pesticidally active ingredients can 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 the compound(s) and milled.
  • Emulsifiable concentrates of the pesticidally active ingredient comprise a convenient concentration, such as from about 10 weight percent to about 50 weight percent of the pesticidally active ingredient, in a suitable liquid, based on the total weight of the concentrate.
  • the pesticidally active ingredients are 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, such as, for example, terpenic solvents, including rosin derivatives, aliphatic ketones, such as cyclohexanone, and complex alcohols, such as 2-ethoxyethanol.
  • Emulsifiers which 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.
  • 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 esterified with the polyol or polyoxyalkylene.
  • Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts.
  • Anionic emulsifiers include the oil-soluble salts (e.g., calcium) of alkylaryl sulfonic acids, oil-soluble salts of sulfated polyglycol ethers and appropriate salts of phosphated polyglycol ether.
  • Representative organic liquids which can be employed in preparing emulsifiable concentrates 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 dim-ethyl amides; and glycol ethers such as the n-butyl ether, ethyl ether or methyl ether of diethylene glycol, and the methyl ether of triethylene glycol and the like. Mixtures of two or more organic liquids may also be employed in the preparation of the emulsifiable concentrate.
  • 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,
  • 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 emulsifying agents.
  • the formulations can also contain other compatible additives, for example, plant growth regulators and other biologically active compounds used in agriculture.
  • Aqueous suspensions comprise suspensions of one or more water-insoluble pesticidally active ingredients 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 one or more of the pesticidally active ingredients, 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. It is often most effective to grind and mix at the same time by preparing the aqueous mixture and homogenizing it in an implement such as a sand mill, ball mill, or piston-type homogenizer.
  • Aqueous emulsions comprise emulsions of one or more water-insoluble pesticidally active ingredients emulsified in an aqueous vehicle at a concentration typically in the range from about 5 to about 50 weight percent, based on the total weight of the aqueous emulsion. If the pesticidally active ingredient is a solid it must be dissolved in a suitable water- immiscible solvent prior to the preparation of the aqueous emulsion.
  • Emulsions are prepared by emulsifying the liquid pesticidally active ingredient or water-immiscible solution thereof into an aqueous medium typically with inclusion of surfactants that aid in the formation and stabilization of the emulsion as described above. This is often accomplished with the aid of vigorous mixing provided by high shear mixers or homogenizers.
  • compositions of the present disclosure can also be granular formulations, which are particularly useful for applications to the soil.
  • Granular formulations usually contain from about 0.5 to about 10 weight percent, based on the total weight of the granular formulation of the pesticidally active ingredient(s), 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 the pesticidally active ingredients 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 the compound is substantially or completely soluble.
  • Such formulations may also be prepared by making a dough or paste of the carrier and the compound and solvent, and crushing and drying to obtain the desired granular particle.
  • Dusts may be prepared by intimately mixing one or more of the pesticidally active ingredients in powdered form with a suitable dusty agricultural carrier, such as, for example, kaolin clay, ground volcanic rock, talc, ground bark, and the like. Dusts can suitably contain from about 1 to about 10 weight percent of the compounds, based on the total weight of the dust.
  • a suitable dusty agricultural carrier such as, for example, kaolin clay, ground volcanic rock, talc, ground bark, and the like. Dusts can suitably contain from about 1 to about 10 weight percent of the compounds, based on the total weight of the dust.
  • the formulations may additionally contain adjuvant surfactants and polymers to enhance adhesion and flowability and decrease dust-off of active ingredients. These adjuvants 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 of sulfosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines and blends of surfactants with mineral or vegetable oils.
  • the formulations may also include oil-in- water emulsions such as those disclosed in U.S. Patent Application Serial No. 11/495,228, the disclosure of which is expressly incorporated by reference herein.
  • the formulations may optionally include combinations that contain other pesticidal compounds, fertilizers, micronutrients, growth stimulants, and biological organisms.
  • additional pesticidal compounds may be fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides or combinations thereof that are compatible with the mixtures of the disclosure described herein in the medium selected for application and not antagonistic to the activity of the present mixtures.
  • the other pesticidal compound is employed as a supplemental toxicant for the same or for a different pesticidal use.
  • the mixtures of the present disclosure and the pesticidal compound in the combination can generally be present in a weight ratio of from 1 : 100 to 100: 1.
  • polymer or "polymeric material” as used in this disclosure is taken to mean either a single polymer or a combination of different polymers or a copolymer.
  • the particle comprises from about 50% to about 99% by weight of the polymeric material, preferably from about 50% to about 90% by weight.
  • suitable polymers for the practice of this disclosure include but are not limited to the following non-exhaustive list of polymers (and copolymers and mixtures thereof): polymethylmethacrylate); poly(lactic acid) (Chronopols 50, 95, and 100) and copolymers such as poly(lactic acid-glycolic acid) copolymers (Lactel BP-400) and
  • polystyrene for example; cellulose acetate butyrate; poly(styrene);
  • polyorthoesters poly(cyanoacrylates); poly(dioxanone); ethyl cellulose; ethyl vinyl acetate polymers and copolymers; poly(ethylene glycol); poly(vinylpyrrolidone); acetylated mono-, di-, and triglycerides; poly(phosphazene); chlorinated natural rubber; vinyl polymers and
  • copolymers polyvinyl chloride; hydroxyalkylcelluloses; polybutadiene; polyurethane;
  • vinylidene chloride polymers and copolymers styrene-butadiene copolymers; styrene-acrylic copolymers; vinyl acetate polymers and copolymers (e.g., vinyl acetate-ethylene copolymers (Vinumuls) and vinyl acetate -vinylpyrrolidone copolymers; alkylvinylether polymers and copolymers; cellulose acetate phthalates; ethyl vinyl pthalates; cellulose triacetate;
  • polyanhydrides polyglutamates; polyhydroxy butyrates; acrylic polymers (Rhoplexes); alkyl acrylate polymers and copolymers; aryl acrylate polymers and copolymers; aryl methacrylate polymers and copolymers; poly(caprolactams) (i.e., the nitrogen-containing counterparts to caprolactones); epoxy/polyamine epoxy/polyamides; polyvinyl alcohol polymers and
  • the polymer used in the compositions of the present disclosure is selected from the group consisting of poly(methylmethacrylate), poly(lactic acid), poly(lactic acid-glycolic acid) copolymers, cellulose acetate butyrate, poly(styrene),
  • hydroxybutyric acid-hydroxyvaleric acid copolymers styrene maleic anhydride copolymers, poly(methylvinyl ether-maleic acid), poly(caprolactone), poly(n-amylmethacrylate), wood rosin, polyanhydrides, polyorthoesters, poly(cyanoacrylates), poly(dioxanone), ethyl cellulose, ethyl vinyl acetate polymers, poly(ethylene glycol), polyvinylpyrrolidone), acetylated mono-, di-, and trigylcerides, poly(phosphazene), chlorinated natural rubber, vinyl polymers, polyvinyl chloride, hydroxyalkylcelluloses, polybutadiene, polyurethane, vinylidene chloride polymers, styrene- butadiene copolymers, styrene-acrylic copolymers, alkylvinylether polymers, cellulose acetate phthal
  • Preferred polymers include poly(methylmethacrylate), poly(lactic acid)
  • Compounds of Formula I are 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 0.5 to about 500 g ai/100 kg seed.
  • the exact amount of a compound of Formula I required varies with the fungal disease to be controlled, the type of formulation employed, the method of application, the timing of the application, the particular plant species, climate conditions, and the like. The dilution and rate of application will depend upon the type of equipment employed, the method and frequency of application desired and diseases to be controlled.
  • a compound of Formula I may also be combined with agricultural fungicides to form fungicidal mixtures and synergistic mixtures thereof and be applied to a seed.
  • the fungi- cidal mixtures are often applied to control a wider variety of undesirable diseases.
  • a compound of Formula I can be formulated with the other fungicide(s), tank mixed with the other fungicide(s) or applied sequentially with the other fungicide(s) to a seed.
  • Such other fungicides include, ametoctradin, azoxystrobin, Bacillus subtilis, benalaxyl, benomyl, benthiavalicarb-isopropyl, bitertanol, bixafen, boscalid, captan, carbendazim, carboxin, carpropamid, chlorothalonil, Coniothyrium minitans, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide, cyazofamid, cyflufenamid, cyproconazole, cyprodinil, diethofencarb, difenoconazole, dimethomorph, dimoxystrobin, enestrobin, epoxiconazole, ethaboxam, famoxadone, fenamidone, fenarimol,
  • imibenconazole iminoctadine, iminoctadine triacetate, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalicarb, isopyrazam, isotianil, mancozeb, mandipropamid, maneb, metalaxyl, mefenoxam, metalaxyl-M, metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate, metiram, metominostrobin, metrafenone, myclobutanil, ofurace, orysastrobin, oxadixyl, oxine- copper, penconazole, penflufen, penthiopyrad, picoxystrobin, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, proquinazi
  • a compound of Formula I may be combined with other pesticides, including insecticides, nematocides, miticides, arthropodicides, bactericides or combinations thereof that are compatible with the compound of Formula I in the medium selected for application, and not antagonistic to the activity of the compound of Formula I to form pesticidal mixtures and synergistic mixtures thereof.
  • a compound of Formula I can be applied in conjunction with one or more other pesticides to control a wider variety of undesirable pests.
  • the compound of Formula I can be formulated with the other pesticide(s), tank mixed with the other pesticide(s) or applied sequentially with the other pesticide(s) to a seed.
  • 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
  • juvenile hormones such as juvenile hormone I, juvenile hormone II and juvenile hormone III; 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; nicotinoid insecticides such as flonicamid; nitroguanidine insecticides such as clothianidin, dinotefuran, imidacloprid and thiamethoxam; nitromethylene insecticides such as nitenpyram and nithiazine;
  • 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
  • quinoxaline organothiophosphate insecticides such as quinalphos and quinalphos-methyl
  • thiadiazole organothiophosphate insecticides such as athidathion, lythidathion, methidathion and prothidathion; triazole organothiophosphate insecticides such as isazofos and triazophos; phenyl organothiophosphate insecticides such as azothoate, bromophos, bromophos-ethyl,
  • phenylphosphonothioate insecticides such as cyanofenphos, EPN and leptophos;
  • phosphoramidate insecticides such as crufomate, fenamiphos, fosthietan, mephosfolan, phosfolan and pirimetaphos; phosphor amidothioate 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 metoxadiazone; phthalimide insecticides such as dialifos, phosmet and tetramethrin; pyrazole insecticides such as tebufenpyrad, tolefenpyrad; phenylpyrazole insecticides such as acetoprole, ethiprole, fipronil, pyraflupro
  • tetronic acid insecticides such as spiromesifen; thiourea insecticides such as diafenthiuron; urea insecticides such as flucofuron and sulcofuron; and unclassified insecticides such as closantel, copper naphthenate, crotamiton, EXD, fenazaflor, fenoxacrim, hydramethylnon, isoprothiolane, malonoben, metaflumizone, nifluridide, plifenate, pyridaben, pyridalyl, pyrifluquinazon, rafoxanide, sulfoxaflor, triarathene and triazamate, and any combinations thereof.
  • a compound of Formula I may be combined with herbicides that are compatible with the compound of Formula I in the medium selected for application and not antagonistic to the activity of the compound of Formula I to form pesticidal mixtures and synergistic mixtures thereof.
  • the compound of Formula I may be applied in conjunction with one or more herbicides to control a wide variety of undesirable plants.
  • a compound of Formula I may be formulated with the herbicide(s), tank mixed with the herbicide(s) or applied sequentially with the herbicide(s).
  • Typical herbicides may 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 and tebutam; anilide herbicides such as chloranocryl, cisanilide, clomeprop, cypromid, diflufenican, etobenzanid, fenasulam, flufenacet, flufenican, mefenacet, mefluidide, metamifop, monalide,
  • 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 pyriminobac; pyrimidinylthiobenzoic acid herbicides such as pyrithiobac; phthalic acid herbicides such as chlorthal; picolinic acid herbicides such as aminopyralid, clopyralid and picloram; quinolinecarboxylic acid herbicides such as quinclorac and quinmerac; arsenical herbicides such as cacodylic acid, CMA, DSMA, hexaflurate, MAA, MAMA, MSMA, potassium arsenite and sodium arsenite; benzoy
  • cyclohexene oxime herbicides such as alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim and tralkoxydim
  • cyclopropylisoxazole herbicides such as isoxachlortole and isoxaflutole
  • dicarboximide herbicides such as cinidon-ethyl, fiumezin, flumiclorac, fiumioxazin and fiumipropyn; dinitroaniline herbicides such as benfiuralin, butralin, dinitramine, ethalfluralin, fiuchloralin, isopropalin, methalpropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin and trifiuralin; dinitrophenol herbicides such as dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etinofen and medinoterb; diphenyl ether herbicides such as ethoxyfen; nitrophenyl ether herbicides such as acifluorfen, aclonifen, bifenox, chlomethoxyfen, chlornitrofen, etnipromid, fluorodifen
  • pyridine herbicides such as aminopyralid, cliodinate, clopyralid, dithiopyr, fluroxypyr, haloxydine, picloram, picolinafen, pyriclor, thiazopyr and triclopyr; pyrimidinediamine herbicides such as iprymidam and tioclorim; quaternary ammonium 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, prosulfo
  • methylthiotriazine herbicides such as ametryn, aziprotryne, cyanatryn, desmetryn,
  • triazinone herbicides such as ametridione, amibuzin, hexazinone, isomethiozin, metamitron and metribuzin
  • triazole herbicides such as amitrole, cafenstrole, epronaz and flupoxam
  • triazolone herbicides such as amicarbazone, bencarbazone, carfentrazone, flucarbazone, ipfencarbazone, propoxycarbazone, sulfentrazone and thiencarbazone-methyl
  • triazolopyrimidine herbicides such as cloransulam, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam and pyroxsulam
  • uracil herbicides such as benzfendizone, bromacil, butafenacil, flupropacil, isoci
  • diflufenzopyr isonoruron, isouron, methabenzthiazuron, monisouron and noruron
  • phenylurea herbicides such as anisuron, buturon, chlorbromuron, chloreturon, chlorotoluron, chloroxuron, daimuron, difenoxuron, dimefuron, diuron, fenuron, fluometuron, fluothiuron, isoproturon, linuron, methiuron, methyldymron, metobenzuron, metobromuron, metoxuron, monolinuron, monuron, neburon, parafluron, phenobenzuron, siduron, tetrafluron and thidiazuron;
  • pyrimidinylsulfonylurea herbicides such as amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, mesosulfuron, metazosulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, propyrisulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron and trifloxysulfuron; triazinylsulfonylurea herbicides such as chlorsulfuron, cinosulfuron, ethametsulfuron, iodosulfuron, metsul
  • 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 seed treatment mixture can also comprise or may be applied together and/or sequentially with further active compounds.
  • further active 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.
  • the seed treatment mixture 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. amyloiquefaciens FZB24 (TAEGRP ® ) and Bacillus amyloiquefaciens FZB42 (RHIZO VITAL ® ), 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. amyloiquefaciens FZB24 (TAEGRP ® ) and Bacillus amyloiquefaciens FZB42 (RHIZO VITAL ®
  • mutants and metabolites of the respective strains that exhibit activity against insects, mites, nematodaes, and/or phytopathogens.
  • Another embodiment of the present disclosure is a method for the control or prevention of fungal attack. This method comprises applying to the seed a fungicidally effective amount of a compound of Formula I.
  • a compound of Formula I is suitable for treatment of various seeds at fungicidal levels, while exhibiting low phytotoxicity. The compound may be useful both in a protectant and/or an eradicant fashion.
  • Compounds of Formula I have been found to have significant fungicidal effects particularly for agricultural use. Compounds of Formula I are particularly effective for use with agricultural crops and horticultural plants. Additional benefits may include, but are not limited to, improving 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); improving the quality of a plant (e.g. improved content or composition of certain ingredients); and improving the tolerance to abiotic and/or biotic stress of the plant.
  • 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); improving the quality of a plant (e.g. improved content or composition of certain ingredients); and improving the tolerance to abiotic and/or biotic stress of the plant.
  • Formula I for the following fungi establish the general utility of the compounds as fungicides.
  • Compounds of Formula I have broad ranges of activity against fungal pathogens.
  • exemplary pathogens may include, but are not limited to, wheat leaf blotch (Septoria tritici; teliomorph: Mycosphaerella graminicola), leaf spot of sugar beets (Cercospora beticola), leaf spots of peanut (Cercospora arachidicola and Cercosporidium personatum) and other crops, Asian soybean rust (Phakopsora pachyrhizi), Barley scald (Rhynchosporium secalis), wheat glume blotch (Leptosphaeria nodorum), wheat brown rust (Puccinia triticina), and wheat powdery mildew (Blumeria graminis f.
  • Method A Seeds of wheat cultivar 'Yuma' were treated with seed dye and a 10% suspension concentrate formulation of either compound 1 or compound 3 (Table 1) at rates of 50, 12.5, 3.1, and 0 grams active ingredient /100 kilograms seeds (g ai/100 kg seeds) and allowed to dry overnight in a fume hood.
  • the treated seeds were planted in pots containing 50% mineral soil/50%) soil-less Metro mix 5 days after treatment, with 10 seeds per pot, and grown in a greenhouse at 20°C.
  • Four pots of the seedlings were then inoculated with each of the pathogens as described below:
  • ERYSGT The 7-day old seedlings were inoculated with B. graminis by dusting with spores from infected stock plants and after inoculation were kept in the greenhouse at 20°C for disease to develop;
  • SEPTTR The 9-day old seedlings were inoculated with an aqueous spore suspension of S. tritici and after inoculation the plants were kept in 100% relative humidity (1 day in a dark dew chamber followed by 2 - 3 days in a lighted dew chamber at 20 °C) to permit spores to germinate and infect the leaf. The plants were then transferred to a greenhouse set at 20 °C for disease to develop;
  • LEPTNO The 9-day old seedlings were inoculated by spraying leaves with an aqueous spore suspension of L. nodorum and after inoculation the plants were kept in 100%) relative humidity (1 day in a dark dew chamber followed by 2 days in a lighted dew chamber at 20 °C) to permit spores to germinate and infect the leaf. The plants were then transferred to a greenhouse set at 20 °C for disease to develop;
  • PUCCRT The 14-day old seedlings were inoculated by spraying leaves with an aqueous spore suspension of P. triticina and after inoculation the plants were kept in 100% relative humidity (1 day in a dark dew chamber at 20 °C) to permit spores to germinate and infect the leaf. The plants were then transferred to a greenhouse set at 24 °C for disease to develop.
  • Method B Seeds of wheat cultivar 'Yuma' were treated with seed polymer, seed dye, and a 10% suspension concentrate formulation of either compound 2 or compound 4 (Table 1) at rates of 300, 100, 33.3, 11, 3.7, and 0 g ai/100 kg seeds and allowed to dry overnight in a fume hood.
  • the treated seeds were planted in pots containing 50%> mineral soil/50%) soil-less metro mix 12 days after treatment, with 10 seeds per pot, and grown in a greenhouse at 20°C.
  • Four pots of 7-day-old seedlings were then inoculated with each of the pathogens as described above.
  • test results from Method A indicated: 1) Compounds 1 and 3 were very active against S. tritici at the lowest test rate of 3.1 g ai/100 kg seeds; 2) Compounds 1 and 3 also showed moderate disease control against the three other pathogens.
  • Control of foliar diseases with these seed treatment applications demonstrates that the experimental compounds are taken up into the xylem and redistributed to leaves in an amount sufficient to provide protectant disease control from a seed treatment. Further, there was no evidence of stunting or phytotoxicity from applications of compounds 1 - 4, even at the highest rates tested. Excellent disease control without phytotoxicity indicates that the classes of chemistry represented by these compounds have potential utility as seed treatments.

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Abstract

L'invention concerne l'utilisation d'un composé de formule I pour traiter des semences afin de prévenir ou de lutter contre les maladies des plantes.
PCT/US2015/039401 2014-07-08 2015-07-07 Picolinamides macrocycliques utilisés pour le traitement des semences WO2016007525A1 (fr)

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EP3052489A4 (fr) * 2013-10-01 2017-05-17 Dow AgroSciences LLC Utilisation de picolinamides macrocycliques en tant que fongicides
US9974304B2 (en) 2013-12-26 2018-05-22 Dow Agrosciences Llc Use of macrocyclic picolinamides as fungicides
US10172354B2 (en) 2012-12-28 2019-01-08 Dow Agrosciences Llc Synergistic fungicidal mixtures for fungal control in cereals
US10173982B2 (en) 2016-08-30 2019-01-08 Dow Agrosciences Llc Picolinamides as fungicides
US10172358B2 (en) 2016-08-30 2019-01-08 Dow Agrosciences Llc Thiopicolinamide compounds with fungicidal activity
US10173971B2 (en) 2014-12-30 2019-01-08 Dow Agrosciences Llc Picolinamides with fungicidal activity
US10173981B2 (en) 2014-12-30 2019-01-08 Dow Agrosciences Llc Picolinamides as fungicides
US10182568B2 (en) 2014-12-30 2019-01-22 Dow Agrosciences Llc Use of picolinamide compounds as fungicides
US10188109B2 (en) 2014-12-30 2019-01-29 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
US10246417B2 (en) 2017-01-05 2019-04-02 Dow Agrosciences Llc Picolinamides as fungicides
US10244754B2 (en) 2016-08-30 2019-04-02 Dow Agrosciences Llc Picolinamide N-oxide compounds with fungicidal activity
US10334852B2 (en) 2016-08-30 2019-07-02 Dow Agrosciences Llc Pyrido-1,3-oxazine-2,4-dione compounds with fungicidal activity
US10433555B2 (en) 2014-12-30 2019-10-08 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
US11155520B2 (en) 2018-03-08 2021-10-26 Dow Agrosciences Llc Picolinamides as fungicides
US11191269B2 (en) 2017-05-02 2021-12-07 Dow Agrosciences Llc Use of an acyclic picolinamide compound as a fungicide for fungal diseases on turfgrasses
US11206828B2 (en) 2017-05-02 2021-12-28 Corteva Agriscience Llc Synergistic mixtures for fungal controls in cereals
US11639334B2 (en) 2018-10-15 2023-05-02 Corteva Agriscience Llc Methods for synthesis of oxypicolinamides
US11771085B2 (en) 2017-05-02 2023-10-03 Corteva Agriscience Llc Synergistic mixtures for fungal control in cereals

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US20130152233A1 (en) * 2011-06-09 2013-06-13 Dow Agrosciences Llc 5-fluorocytosine as a seed treatment agent to control plant disease
US20140187588A1 (en) * 2012-12-31 2014-07-03 Dow Agrosciences Llc Macrocyclic picolinamides as fungicides

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EP1013169A1 (fr) * 1997-08-29 2000-06-28 Meiji Seika Kaisha Ltd. Agent de lutte contre la piriculariose du riz et agent de lutte contre la tavelure du ble
US20040192924A1 (en) * 2001-10-23 2004-09-30 Meyer Kevin Gerald Derivatives of uk-2a
US20130152233A1 (en) * 2011-06-09 2013-06-13 Dow Agrosciences Llc 5-fluorocytosine as a seed treatment agent to control plant disease
US20140187588A1 (en) * 2012-12-31 2014-07-03 Dow Agrosciences Llc Macrocyclic picolinamides as fungicides

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10172354B2 (en) 2012-12-28 2019-01-08 Dow Agrosciences Llc Synergistic fungicidal mixtures for fungal control in cereals
EP3052489A4 (fr) * 2013-10-01 2017-05-17 Dow AgroSciences LLC Utilisation de picolinamides macrocycliques en tant que fongicides
EP3052488A4 (fr) * 2013-10-01 2017-05-24 Dow AgroSciences LLC Composés de picolinamide macrocycliques à activité fongicide
US9974304B2 (en) 2013-12-26 2018-05-22 Dow Agrosciences Llc Use of macrocyclic picolinamides as fungicides
US10595531B2 (en) 2014-12-30 2020-03-24 Dow Agrosciences Llc Use of picolinamide compounds as fungicides
US10252989B2 (en) 2014-12-30 2019-04-09 Dow Agrosciences Llc Picolinamides with fungicidal activity
US10173971B2 (en) 2014-12-30 2019-01-08 Dow Agrosciences Llc Picolinamides with fungicidal activity
US10173981B2 (en) 2014-12-30 2019-01-08 Dow Agrosciences Llc Picolinamides as fungicides
US10182568B2 (en) 2014-12-30 2019-01-22 Dow Agrosciences Llc Use of picolinamide compounds as fungicides
US10188109B2 (en) 2014-12-30 2019-01-29 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
US11751568B2 (en) 2014-12-30 2023-09-12 Corteva Agriscience Llc Picolinamide compounds with fungicidal activity
US10588318B2 (en) 2014-12-30 2020-03-17 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
US10433555B2 (en) 2014-12-30 2019-10-08 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
US10334852B2 (en) 2016-08-30 2019-07-02 Dow Agrosciences Llc Pyrido-1,3-oxazine-2,4-dione compounds with fungicidal activity
US10244754B2 (en) 2016-08-30 2019-04-02 Dow Agrosciences Llc Picolinamide N-oxide compounds with fungicidal activity
US10172358B2 (en) 2016-08-30 2019-01-08 Dow Agrosciences Llc Thiopicolinamide compounds with fungicidal activity
US10231452B2 (en) 2016-08-30 2019-03-19 Dow Agrosciences Llc Thiopicolinamide compounds with fungicidal activity
US10173982B2 (en) 2016-08-30 2019-01-08 Dow Agrosciences Llc Picolinamides as fungicides
US10214490B2 (en) 2016-08-30 2019-02-26 Dow Agrosciences Llc Picolinamides as fungicides
US10246417B2 (en) 2017-01-05 2019-04-02 Dow Agrosciences Llc Picolinamides as fungicides
US11191269B2 (en) 2017-05-02 2021-12-07 Dow Agrosciences Llc Use of an acyclic picolinamide compound as a fungicide for fungal diseases on turfgrasses
US11206828B2 (en) 2017-05-02 2021-12-28 Corteva Agriscience Llc Synergistic mixtures for fungal controls in cereals
US11771085B2 (en) 2017-05-02 2023-10-03 Corteva Agriscience Llc Synergistic mixtures for fungal control in cereals
US11155520B2 (en) 2018-03-08 2021-10-26 Dow Agrosciences Llc Picolinamides as fungicides
US11639334B2 (en) 2018-10-15 2023-05-02 Corteva Agriscience Llc Methods for synthesis of oxypicolinamides

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