US20180000082A1 - 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one as a seed treatment - Google Patents

5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one as a seed treatment Download PDF

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US20180000082A1
US20180000082A1 US15/537,940 US201515537940A US2018000082A1 US 20180000082 A1 US20180000082 A1 US 20180000082A1 US 201515537940 A US201515537940 A US 201515537940A US 2018000082 A1 US2018000082 A1 US 2018000082A1
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Prior art keywords
seedling
seed
plant
plant seed
compound
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Carla J.R. Klittich
Chenglin Yao
W. John OWEN
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Adama Makhteshim Ltd
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Adama Makhteshim Ltd
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Priority to US15/537,940 priority Critical patent/US20180000082A1/en
Publication of US20180000082A1 publication Critical patent/US20180000082A1/en
Assigned to DOW AGROSCIENCES LLC reassignment DOW AGROSCIENCES LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KLITTICH, CARLA R., YAO, CHENGLIN, OWEN, W. JOHN
Assigned to ADAMA MAKHTESHIM, LTD. reassignment ADAMA MAKHTESHIM, LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DOW AGROSCIENCES LLC
Abandoned legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01CPLANTING; SOWING; FERTILISING
    • A01C1/00Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
    • A01C1/06Coating or dressing seed
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/541,3-Diazines; Hydrogenated 1,3-diazines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine

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.
  • One aspect 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, wherein: R 1 is selected from H, C 1 -C 6 alkyl, and C 1 -C 6 alkoxy, and R 2 is selected from C 1 -C 6 alkyl, phenyl, benzyl, and —CH 3 -thiophenyl.
  • a method of treating a plant seed to produce a plant resistant to fungal attack wherein the plant seed is treated with a compound of Formula I.
  • R 1 and R 2 are independently selected from C 1 -C 6 alkyl.
  • R 1 and R 2 are each —CH 3 .
  • the compound of Formula I is applied at a rate from about 0.5 to about 500 grams per 100 kilograms of seed.
  • the seed being treated is a wheat seed ( Triticum sp.; TRZSS).
  • the fungal pathogen is selected from the group consisting of the causal agent of wheat leaf blotch ( Zymoseptoria tritici ), leaf spot of sugar beets ( Cercospora beticola ), and leaf spot of peanut ( Cercospora arachidicola and Cercosporidium personatum ).
  • a plant seed adapted to produce a plant resistant to fungal and insect attack is provided.
  • the plant seed is treated with a compound of Formula I and one or more insecticides.
  • R 1 and R 2 are each —CH 3 .
  • a plant seed adapted to produce a plant resistant to fungal and insect attack is provided.
  • the plant seed is treated with a compound of Formula I and one or more fungicides.
  • R 1 and R 2 are each —CH 3 .
  • a plant seed adapted to produce a plant resistant to fungal and insect attack is provided.
  • the plant seed is treated with a compound of Formula I and one or more insecticides.
  • R 1 and R 2 are each —CH 3 .
  • a plant seed adapted to produce a plant resistant to fungal attack is provided.
  • the plant seed is treated with a compound of Formula I and one or more additional health stimulators selected from the group consisting of organic compounds, inorganic fertilizers or micronutrient donors, biocontrol agents and inoculants.
  • R 1 and R 2 are each —CH 3 .
  • a method of treating a plant seedling to produce a plant resistant to fungal attack is provided.
  • the plant seedling is treated with a compound of Formula I.
  • R 1 and R 2 are each —CH 3 .
  • the seedling is a seedling of wheat ( Triticum sp.; TRZSS).
  • the fungal pathogen is selected from the group consisting of the causal agent of wheat leaf blotch ( Zymoseptoria tritici ), leaf spot of sugar beets ( Cercospora beticola ), and leaf spot of peanut ( Cercospora arachidicola and Cercosporidium personatum ).
  • a plant seedling adapted to produce a plant resistant to fungal and insect attack is provided.
  • the plant seedling is treated with a compound of Formula I and one or more insecticides.
  • R 1 and R 2 are each —CH 3 .
  • a plant seedling adapted to produce a plant resistant to fungal and insect attack is provided.
  • the plant seedling is treated with a compound of Formula I and one or more fungicides.
  • R 1 and R 2 are each —CH 3 .
  • a plant seedling adapted to produce a plant resistant to fungal and insect attack is provided.
  • the plant seedling is treated with a compound of Formula I and one or more insecticides.
  • R 1 and R 2 are each —CH 3 .
  • a plant seedling adapted to produce a plant resistant to fungal attack is provided.
  • the plant seedling is treated with a compound of Formula I and one or more additional health stimulators selected from the group consisting of organic compounds, inorganic fertilizers or micronutrient donors, biocontrol agents and inoculants.
  • R 1 and R 2 are each —CH 3 .
  • a plant seedling adapted to produce a plant resistant to fungal attack.
  • the plant seedling is treated with a compound of Formula I.
  • R 1 and R 2 are each —CH 3 .
  • a method of protecting a plant from fungal attack comprises applying a compound of Formula I to the seedling environment.
  • the compound of Formula I is provided as a liquid formulation.
  • the compound of Formula I is provided as a solid formulation.
  • 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.
  • the present disclosure contemplates all vehicles by which a compound of 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.
  • 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 dimethyl 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, particularly the dimethyl
  • 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 Ser. 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.
  • 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): poly(methylmethacrylate); poly(lactic acid) (Chronopols 50, 95, and 100) and copolymers such as poly(lactic acid-glycolic acid) copolymers (Lactel BP-400) and combinations with polystyrene, for example; cellulose acetate butyrate; poly(styrene); hydroxybutyric acid-hydroxyvaleric acid copolymers (Biopol D400G); styrene maleic anhydride copolymers (SMA 1440 A Resin, Sartomer Co.); poly(methylvinyl ether-maleic acid); poly(caprolactone); poly(n-amylmethacrylate); wood rosin; polyanhydrides, e.g., poly(sebacic anhydride), poly(valeric anhydride), poly(trimethylene carbonate
  • 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), poly(vinylpyrrolidone), acetylated mono-, di-, and trigylcerides, poly(phosphazene), chlorinated natural rubber, vinyl polymers, polyvinyl chloride, hydroxyalky
  • Preferred polymers include poly(methylmethacrylate), poly(lactic acid) (Chronopols 50, 95, or 100), and combinations with polystyrene, poly(lactic acid-glycolic acid) copolymers (Lactel BP-400), cellulose acetate butyrate, and poly(styrene).
  • 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 fungicidal 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, fenari
  • 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
  • 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,
  • the seed treatment mixture 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.
  • 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 (RHIZOVITAL®), 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 (RHIZOVITAL®
  • 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 plants 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.
  • Compounds of Formula I have broad ranges of activity against fungal pathogens.
  • exemplary pathogens may include, but are not limited to, wheat leaf blotch ( Zymoseptoria trilici ), leaf spot of sugar beets ( Cercospora beticola ), leaf spot of peanut ( Cercospora arachidicola and Cercosporidium personatum ).
  • the exact amount of the active material to be applied is dependent not only on the specific formulation 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.
  • Control of foliar diseases with these seed treatment applications demonstrates that the experimental compound is 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 compound 1, even at the highest rates tested. Excellent disease control without phytotoxicity indicates that the classes of chemistry represented by compounds of Formula I have potential utility as seed treatments.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Pretreatment Of Seeds And Plants (AREA)
US15/537,940 2014-12-23 2015-12-18 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one as a seed treatment Abandoned US20180000082A1 (en)

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US201462096301P 2014-12-23 2014-12-23
PCT/US2015/066756 WO2016106138A1 (en) 2014-12-23 2015-12-18 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one as a seed treatment
US15/537,940 US20180000082A1 (en) 2014-12-23 2015-12-18 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one as a seed treatment

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US10059703B2 (en) 2012-12-31 2018-08-28 Adama Makhteshim Ltd. 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides
WO2020095181A1 (en) 2018-11-05 2020-05-14 Adama Makhteshim Ltd. Mixtures and compositions comprising 5-fluoro-4-imino-3- methyl-1-tosyl-3,4-dihydropyrimidin-2-one, and methods of use thereof
WO2021014346A1 (en) 2019-07-22 2021-01-28 Adama Makhteshim Ltd. Fungicidal combinations, mixtures and compositions and uses thereof
US10919864B2 (en) 2013-12-31 2021-02-16 Adama Makhteshim Ltd. 5-fluoro-4-imino-3(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation
WO2021224802A1 (en) 2020-05-04 2021-11-11 Adama Makhteshim Ltd. Mixtures and compositions comprising 5-fluoro-4-imino-3- methyl-1-tosyl-3,4-dihydropyrimidin-2-one, and methods of use thereof
WO2022162591A1 (en) 2021-01-27 2022-08-04 Adama Makhteshim Ltd. 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1 h)-one for controlling plant diseases
WO2022234487A1 (en) 2021-05-04 2022-11-10 Adama Makhteshim Ltd. Crystalline forms of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4- dihydropyrimidin-2-one, and mixtures, compositions and methods of use thereof
US11632954B2 (en) 2017-07-17 2023-04-25 Adama Makhteshim Ltd. Polymorphs of 5-fluoro-4-imino-3-methyl-1 -tosyl-3,4-dihydropyrimidin-2-one
WO2023166485A1 (en) 2022-03-03 2023-09-07 Adama Makhteshim Ltd. Fungicidal combinations, mixtures and compositions and uses thereof
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WO2017221092A1 (en) 2016-06-20 2017-12-28 Novartis Ag Triazolopyridine compounds and uses thereof
WO2017221100A1 (en) 2016-06-20 2017-12-28 Novartis Ag Imidazopyrimidine compounds useful for the treatment of cancer
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TWI774762B (zh) * 2017-05-02 2022-08-21 美商科迪華農業科技有限責任公司 非環狀吡啶醯胺作為一種殺真菌劑以防治蔬菜中植物病原性真菌的用途
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
TWI801380B (zh) * 2017-05-02 2023-05-11 美商科迪華農業科技有限責任公司 一種非環狀吡啶醯胺化合物作為殺真菌劑以防治在果園、葡萄藤園及農園作物中的植物病原性真菌之用途
KR102659552B1 (ko) * 2017-05-02 2024-04-23 코르테바 애그리사이언스 엘엘씨 잔디풀 상의 진균 질환에 대한 살진균제로서의 비고리형 피콜린아미드 화합물의 용도
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Cited By (16)

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US10059703B2 (en) 2012-12-31 2018-08-28 Adama Makhteshim Ltd. 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides
US10045534B2 (en) 2013-12-31 2018-08-14 Adama Makhteshim Ltd. Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control
US10051862B2 (en) 2013-12-31 2018-08-21 Adama Makhteshim Ltd. Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control
US10426167B2 (en) 2013-12-31 2019-10-01 Adama Makhteshim Ltd. Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control
US10426165B2 (en) 2013-12-31 2019-10-01 Adama Makhteshim Ltd. Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control
US10426166B2 (en) 2013-12-31 2019-10-01 Adama Makhteshim Ltd. Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control
US10045533B2 (en) 2013-12-31 2018-08-14 Adama Makhteshim Ltd. Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control
US10919864B2 (en) 2013-12-31 2021-02-16 Adama Makhteshim Ltd. 5-fluoro-4-imino-3(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation
US11632954B2 (en) 2017-07-17 2023-04-25 Adama Makhteshim Ltd. Polymorphs of 5-fluoro-4-imino-3-methyl-1 -tosyl-3,4-dihydropyrimidin-2-one
WO2020095181A1 (en) 2018-11-05 2020-05-14 Adama Makhteshim Ltd. Mixtures and compositions comprising 5-fluoro-4-imino-3- methyl-1-tosyl-3,4-dihydropyrimidin-2-one, and methods of use thereof
WO2021014346A1 (en) 2019-07-22 2021-01-28 Adama Makhteshim Ltd. Fungicidal combinations, mixtures and compositions and uses thereof
WO2021224802A1 (en) 2020-05-04 2021-11-11 Adama Makhteshim Ltd. Mixtures and compositions comprising 5-fluoro-4-imino-3- methyl-1-tosyl-3,4-dihydropyrimidin-2-one, and methods of use thereof
WO2022162591A1 (en) 2021-01-27 2022-08-04 Adama Makhteshim Ltd. 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1 h)-one for controlling plant diseases
WO2022234487A1 (en) 2021-05-04 2022-11-10 Adama Makhteshim Ltd. Crystalline forms of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4- dihydropyrimidin-2-one, and mixtures, compositions and methods of use thereof
WO2023166485A1 (en) 2022-03-03 2023-09-07 Adama Makhteshim Ltd. Fungicidal combinations, mixtures and compositions and uses thereof
WO2023228148A1 (en) 2022-05-26 2023-11-30 Adama Makhteshim Ltd. Fungicidal combinations, mixtures and compositions and uses thereof

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ZA201704838B (en) 2020-11-25
BR122020000183B1 (pt) 2022-04-26
AU2015369906A8 (en) 2017-08-03
KR20170105527A (ko) 2017-09-19
BR112017013733B1 (pt) 2021-08-10
MX2017008370A (es) 2018-04-30
PE20171098A1 (es) 2017-08-07
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AU2015369906A1 (en) 2017-07-27
CO2017007059A2 (es) 2017-10-10
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