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WO2025052473A1 - Composition fongicide comprenant du valifénalate et du dithiocarbamate - Google Patents

Composition fongicide comprenant du valifénalate et du dithiocarbamate Download PDF

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Publication number
WO2025052473A1
WO2025052473A1 PCT/IN2024/051670 IN2024051670W WO2025052473A1 WO 2025052473 A1 WO2025052473 A1 WO 2025052473A1 IN 2024051670 W IN2024051670 W IN 2024051670W WO 2025052473 A1 WO2025052473 A1 WO 2025052473A1
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WO
WIPO (PCT)
Prior art keywords
composition
valifenalate
range
microns
parts
Prior art date
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Application number
PCT/IN2024/051670
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English (en)
Inventor
Rajiv Rathod
Ramdas Puthenveetil Kunjukrishna Menon
Jayprakash Rao
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Individual
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Individual
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Publication of WO2025052473A1 publication Critical patent/WO2025052473A1/fr
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    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring

Definitions

  • the present invention relates to a synergistic fungicidal composition
  • a synergistic fungicidal composition comprising an effective amount of Valifenalate or agriculturally acceptable salts thereof and an effective amount of a dithiocarbamate compound selected from Metiram and Propineb or their agriculturally acceptable salts and at least one agrochemically acceptable excipient.
  • the invention relates to a fungicidal composition
  • a fungicidal composition comprising: valifenalate or agriculturally acceptable salts thereof in the range of 0.1% w/w to 50% w/w of the total composition; a dithiocarbamate compound selected from propineb and metiram or their agriculturally acceptable salts, wherein the dithiocarbamate compound is present in the range 0.1% w/w to 70% w/w of the total composition; and, at least one agrochemically acceptable excipient.
  • the fungicidal composition comprises of particles in the size range of 0.1 micron to 50 microns.
  • the invention further relates to the process of preparing the fungicidal composition comprising an effective amount of Valifenalate or agriculturally acceptable salts thereof and an effective amount of a dithiocarbamate compound selected from propineb and metiram or their agriculturally acceptable salts.
  • the invention furthermore relates to a method of controlling fungal disease, crop protection or improving plant health or yield by treating a plant, crop, plant propagation material, locus or parts thereof, a seed, seedling or surrounding soil with the fungicidal composition of the present invention.
  • Valifenalate is an anti-peronosporic fungicide that controls various types of fungal infections in many crops, including grapes, potatoes, and tomatoes. It acts by inhibiting the cell metabolism, particularly the synthesis of the fungal cell wall.
  • Propineb is a polymeric zinc-containing dithiocarbamate compound, a contact fungicide with a broad spectrum activity against various diseases of rice, chilli, grapes, potato and other vegetables and fruits. Due to the release of zinc, the application of Propineb results in a greening effect on the crop and subsequent improvement in the quality of the produce. Propineb interferes at different locations in the metabolism of the fungi; at several points in the respiration chain; in the metabolism of carbohydrates and proteins and in the cell membranes.
  • Metiram is a broad spectrum contact fungicide from the dithiocarbamate group used for a wide range of crops. It provides broad-spectrum disease protection with a safe Zinc (14%) supplement, which helps in better crop health. Metiram is used to protect fruits, vegetables, field crops, and ornamentals from foliar diseases and damping off.
  • compositions which is known in the art comprising a specific composition of Valifenalate in combination with a dithiocarbamate compound selected from propineb and metiram; which is not only synergistic in nature, but can also be effectively used with a broad spectrum fungicidal activity at lower dosage and address the drawbacks discussed above with the known compositions.
  • the inventors have surprisingly found that the composition comprising an effective amount of Valifenalate or agrochemically acceptable salts thereof and an effective amount of dithiocarbamate compound selected from propineb and metiram or their agrochemically acceptable salts exhibits synergy.
  • the inventors have developed a stable synergistic fungicidal composition
  • a stable synergistic fungicidal composition comprising Valifenalate or agriculturally acceptable salts thereof in the range of 0.1% w/w to 50% w/w of the total composition and a dithiocarbamate compound selected from propineb and metiram or their agriculturally acceptable salts, wherein the dithiocarbamate compound is present in the range 0.1% w/w to 70% w/w of the total composition and at least one agrochemically acceptable excipient, where the composition acts as a superior crop-protectant, is non-phytotoxic, is effective at reduced dosages of application, helps in the resistance management observed with the old pesticide chemistry and also demonstrates increased yield on field application, while broadening the spectrum of crop protection in terms of fungus or disease control.
  • the fungicidal composition of the invention comprises of particles in the size range of 0.1 micron to 50 microns and thereby exhibits superior physical characteristics such as suspensibility, dispersibility, flowability and wettability.
  • the fungicidal composition exhibits an increased surface area coverage on application to the crops or the plants, which enhances adhesion and provides better penetration of the active moieties when applied to the foliage improving the efficacy and bioavailability of the composition.
  • the particle size range of 0.1-50 microns of the fungicidal composition was found to be significant not only in terms of ease of application but also in terms of efficacy.
  • the compositions of the present invention also demonstrated superior performance under accelerated storage and also surprisingly be used effectively in modern irrigation systems. 3.
  • the present invention relates to a synergistic fungicidal composition
  • a synergistic fungicidal composition comprising effective amount of Valifenalate or agriculturally acceptable salts thereof; a dithiocarbamate compound selected from Propineb and Metiram or their agriculturally acceptable salts and at least one agrochemically acceptable excipient; wherein the composition comprises particles in the size range of 0.1 micron to 50 microns.
  • valifenalate or agriculturally acceptable salts thereof is present in the range of 0.1% w/w to 50% w/w of the total composition and the dithiocarbamate compound or agriculturally acceptable salts thereof is present in the range 0.1% w/w to 70% w/w of the total composition.
  • the invention relates to a method of protection of the crop or improving its health or yield, by treating at least one of a plant or parts thereof, a plant propagation material, seed or seedling, with a fungicidal composition comprising an effective amount of valifenalate, an effective amount of dithiocarbamate compound selected from propineb and metiram or their agriculturally acceptable salts, wherein the composition comprises particles in the size range of 0.1 micron to 50 microns. 4.
  • a fungicidal composition comprising an effective amount of valifenalate, an effective amount of dithiocarbamate compound selected from propineb and metiram or their agriculturally acceptable salts, wherein the composition comprises particles in the size range of 0.1 micron to 50 microns.
  • the particle size of the composition is defined as the size of particles of the composition in the form of water dispersible granules (WG) or wettable powders (WP) or liquid suspension (SC) or oil dispersion (OD), as a whole comprising the active ingredients i.e. Valifenalate and the dithiocarbamate compound selected from Propineb or Metiram along with the agrochemically acceptable excipient/s.
  • D50 is the corresponding particle size when the cumulative percentage reaches 50%.
  • D50 is also called the median particle diameter or median particle size and represent an average 50% of the total particles to be smaller than the determined size.
  • D90 is used to indicate particle size distribution and represent average 90% of the total particles to be smaller than the determined size.
  • D90 is also the corresponding particle size when the cumulative percentage reaches
  • a mixture is defined as a combination of two or more substances that are not chemically united to each other.
  • a homogeneous mixture is defined as one whose composition is uniform throughout the mixture or the components that make up the mixture are distributed uniformly.
  • the present invention relates to a synergistic fungicidal composition comprising an effective amount of valifenalate, an effective amount of a dithiocarbamate compound selected from propineb and metiram and at least one agrochemically acceptable excipient.
  • the fungicidal composition comprising: valifenalate or agriculturally acceptable salts thereof in the range of 0.1% w/w to 50% w/w of the total composition; a dithiocarbamate compound selected from propineb and metiram or their agriculturally acceptable salts, wherein the dithiocarbamate compound is present in the range 0.1% w/w to 70% w/w of the total composition; and at least one agrochemically acceptable excipient, where the composition has a particle size range of 0.1 to 50 microns demonstrated synergistic pesticidal activity compared to the activity of the individual active ingredient alone.
  • Propineb is present in the range of 5% to 40% w/w of the total composition. According to an embodiment, Propineb is present in the range of 5% to 30% w/w of the total composition. According to an embodiment, Propineb is are present in the range of 5% to 20% w/w of the total composition. According to an embodiment, Propineb is present in the range of 5% to 10% w/w of the total composition. According to an embodiment, the fungicidal composition comprises valifenalate or agriculturally acceptable salts thereof in the range of 0.1% w/w to 50% w/w of the total composition and metiram or agriculturally acceptable salts thereof in the range 0.1% w/w to 70% w/w of the total composition.
  • Metiram is present in the range of 1% to 70% w/w of the total composition. According to an embodiment, Metiram is present in the range of 5% to 70% w/w of the total composition. According to an embodiment, Metiram is present in the range of 5% to 60% w/w of the total composition. According to an embodiment, Metiram is present in the range of 5% to 50% w/w of the total composition. According to an embodiment, Metiram is present in the range of 5% to 40% w/w of the total composition. According to an embodiment, Metiram is present in the range of 5% to 30% w/w of the total composition. According to an embodiment, Metiram is present in the range of 5% to 20% w/w of the total composition.
  • Metiram is present in the range of 5% to 10% w/w of the total composition.
  • the fungicidal composition is in the form of a solid, a liquid or a gel or a paste.
  • the solid composition is in the form of one of wettable powders, dispersible powders, broadcast granules, spheronized granules, extruded granules, water dispersible granules, water disintegrable granules, dry capsulated suspension and a dry ZC composition (combination of capsulated suspension and suspension concentrate).
  • the water disintegrable granular composition is in a size range of 0.05 mm to 4 mm.
  • the solid composition is preferably in the form of one of wettable powders and water dispersible granules.
  • the water dispersible granules are in a size range of 0.05 mm to 4 mm.
  • the water dispersible granules are preferably, in a size range of 0.05 mm to 3 mm.
  • the water dispersible granules are preferably, in a size range of 0.05 mm to 2 mm.
  • the water dispersible granules are preferably, in a size range of 0.05 mm to 1.5 mm.
  • the water dispersible granules are preferably, in a size range of 0.05 mm to 1 mm.
  • the solid composition comprises valifenalate or agriculturally acceptable salts thereof in the range of 0.1% w/w to 50% w/w of the total composition and the dithiocarbamate compound selected from metiram and propineb or their agriculturally acceptable salts in the range of 0.1% w/w to 70% w/w of the total composition.
  • the fungicidal composition in the form of granules and wettable powders comprise particles in the size range of 0.1 micron to 50 microns.
  • the fungicidal composition in the form of water dispersible granules and wettable powders preferably comprise particles in the size range of 0.1 micron to 40 microns.
  • the fungicidal composition in the form of water dispersible granules and wettable powders preferably comprise particles in the size range of 0.1 micron to 30 microns.
  • the fungicidal composition in the form of granules or wettable powders disperses into particles in the size range of 0.1 micron to 50 microns, on addition to water.
  • the fungicidal composition in the form of water dispersible granules or wettable powders disperses into particles in the size range of 0.1 micron to 30 microns, on addition to water.
  • the fungicidal composition in the form of water dispersible granules or wettable powders comprise particles having diameter distribution of D90 of about 30 microns.
  • the fungicidal composition in the form of water dispersible granules or wettable powders comprise particles having diameter distribution of D90 of about 20 microns.
  • the fungicidal composition in the form of water dispersible granules or wettable powders comprise particles having diameter distribution of D90 of about 10 microns.
  • the fungicidal composition in the form of water dispersible granules or wettable powders comprise particles having diameter distribution of D50 of about 20 microns.
  • the fungicidal composition in the form of water dispersible granules or wettable powders comprise particles having diameter distribution of D50 of about 10 microns.
  • the liquid composition is in the form of one of solutions, suspension, oil dispersion, liquid suspension, flowable concentrate, seed dressing, suspo- emulsion, capsulated suspension, combination of capsulated suspension and suspension concentrate (ZC).
  • the liquid composition is preferably, in the form of one of liquid suspension and oil dispersion.
  • the liquid composition comprises valifenalate or agriculturally acceptable salts thereof in the range of 0.1% w/w to 30% w/w of the total composition and the dithiocarbamate compound selected from metiram and propineb or their agriculturally acceptable salts in the range of 0.1% w/w to 45% w/w of the total composition.
  • the fungicidal composition in the form of liquid suspension or oil dispersion disperses into particles in the size range of 0.1 micron to 30 microns, on addition to water. According to an embodiment, the fungicidal composition in the form of liquid suspension or oil dispersion disperses into particles in the size range of 0.1 micron to 20 microns, on addition to water. According to another embodiment, the fungicidal composition of the invention in the form of liquid suspension or oil dispersion comprise particles having diameter distribution of D90 of about 20 microns. According to another embodiment, the fungicidal composition of the invention in the form of liquid suspension or oil dispersion comprise particles having diameter distribution of D90 of about 10 microns.
  • the dispersing agent is present in an amount of 0.1% to 40% by weight of the total composition. According to an embodiment, the dispersing agent is present in an amount of 0.1% to 30% by weight of the total composition. According to an embodiment, the dispersing agent is present in an amount of 0.1% to 20% by weight of the total composition.
  • the wetting agents used in the fungicidal composition include, but are not limited to one or more of phenol naphthalene sulphonates, alkyl naphthalene sulfonate, sodium alkyl naphthalene sulfonate, naphthalene sulphonate sodium salt, dibutylnaphthalene- sulfonic acid, alkylarylsulfonates, dioctyl sulfosuccinate, polyoxyethoxylated fatty alcohols, alkane sulfonates, alkylbenzene sulfonates, alkyl ether phosphates, alkyl ether sulphates and alkyl sulfosuccinic monoesters, salts, derivatives thereof.
  • the wetting agent is present in an amount of 0.1% to 30% by weight of the total composition. According to an embodiment, the wetting agent is present in an amount of 0.1% to 20% by weight of the total composition. According to an embodiment, the wetting agent is present in an amount of 0.1% to 10% by weight of the total composition.
  • the carriers that are used in the fungicidal composition of the present invention include, but are not limited to one or more of solid carriers or fillers or diluents. According to another embodiment, the carriers include mineral carriers, plant carriers, synthetic carriers, water-soluble carriers.
  • the solid carriers include natural minerals like clay such as china clay, acid clay, kaolin such as kaolinite, dickite, nacrite, and synthetic and diatomaceous silicas, micas, such as pyrophyllite, talc, silicas such as cristobalite and quartz, such as attapulgite and sepiolite, vermiculite, laponite, pumice, bauxite, hydrated aluminas, perlite, sodium bicarbonate, limestone, natural and synthetic silicates, silicas,surface-modified silicas, zeolite, diatomaceous earth, loess, mirabilite, white carbon, slaked lime, synthetic silicic acid, starch, modified starch, cellulose, plant carriers such as cellulose, chaff, wheat flour, wood flour, starch, rice bran, wheat bran, and soybean flour, casein sodium,
  • the carrier is present in an amount of 0.1% to 95% by weight of the composition. According to a further embodiment, the carrier is present in an amount of 0.1% to 80% by weight of the composition. According to a further embodiment, the carrier is present in an amount of 0.1% to 70% by weight of the composition. According to a further embodiment, the carrier is present in an amount of 0.1% to 50% by weight of the composition. According to an embodiment, solvent comprises water miscible solvents.
  • solvent comprises water immiscible solvents.
  • water immiscible solvents include aromatic and non-aromatic hydrocarbons, halogenated aromatic and non- aromatic hydrocarbons, petroleum distillates, aromatic and non-aromatic ethers, esters or amides, oils or mixtures thereof.
  • the oils can be one or more of a mineral oil, petroleum oil, vegetable oil or animal oil or derivatives or mixtures thereof.
  • the mineral oil or petroleum oil can be one or more of aliphatic or isoparaffinic series, and mixtures of aromatic and aliphatic hydrocarbons; halogenated aromatic or aliphatic hydrocarbons.
  • Paraffinic oil can be selected from linear or branched C8 to C30 paraffins for example such as octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, their mixtures, or mixtures thereof with higher boiling homologs, such as hepta-, octa-, nona- decane, eicosane, heneicosane, docosane, tricosane, tetracosane, pentacosane, and the branched chain isomers thereof, unsubstituted or substitutedaromatic or cycloaliphatic C7 to C18 hydrocarbon compounds such as mono- or
  • Esters which can be used in the oil dispersions of the invention are benzyl acetate, caproic acid ethyl ester, pelargonic acid ethyl ester, benzoic acid methyl or ethyl ester, salicylic acid methyl, propyl, or butyl ester, diesters of phthalic acid with saturated aliphatic or alicyclic Cl to C12 alcohols, such as phthalic acid dimethyl ester, dibutyl ester, diisooctyt ester, or liquid amides of C1-C3 amines, alkylamines or alkanolamines with C6 - C18 carboxylic acids or derivatives or mixtures thereof.
  • the vegetable oils can be one or more of seed oil.
  • the vegetable oils can also include one or more of soy bean oil, rape seed oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil, cotton seed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, kapok oil, papaya oil, camellia oil, rice bran oil, tung oil and the like; and esters of the above vegetable oils, or transesterification products thereof such as soy bean oilmethyl esters, ethyl esters, propyl esters, butyl esters or derivatives thereof.
  • the animal oil can be one or more of whale oil, cod-liver oil, or mink oil.
  • the petroleum distillates include one or more of aromatic hydrocarbons derived from benzene, such as toluene, xylenes, other alkylated benzenes and the like, and naphthalene derivatives, aliphatic hydrocarbons such as hexane, octane, cyclohexane, and the like, mineral oils from the aliphatic or isoparaffinic series, and mixtures of aromatic and aliphatic hydrocarbons; halogenated aromatic or aliphatic hydrocarbons; vegetable, seed or animal oils such as soybean oil, rape seed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cotton seed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil,
  • the composition includes organic solvents or cosolvents such as ethers like tetrahydrofuran and the like, alkylene glycol dialkyl ethers such as ethylene glycol diethyl ether and the like, amides such as dimethylformamide, dimethylacetamide or N-methylpyrrolidone and the like, ketones such as methyl ethyl ketone and the like, nitriles such as butyronitrile and the like, sulfoxides or sulfones such as dimethyl sulfoxide or sulfolane and the like, and alkylene carbonates such as propylene or butylene carbonate.
  • organic solvents or cosolvents such as ethers like tetrahydrofuran and the like, alkylene glycol dialkyl ethers such as ethylene glycol diethyl ether and the like, amides such as dimethylformamide, dimethylacetamide or N-methylpyrrolidone and the like, ketones such
  • the water immiscible solvent is present in the concentration of 0.1% to 90% by weight of total composition. According to an embodiment, the water immiscible solvent is present in the concentration of 0.1% to 80% by weight of total composition. According to an embodiment, the water immiscible solvent is present in the concentration of 0.1% to 70% by weight of total composition. According to an embodiment, the water immiscible solvent is present in the concentration of 0.1% to 60% by weight of total composition. According to an embodiment, the water immiscible solvent is present in the concentration of 0.1% to 50% by weight of total composition. According to an embodiment, the water immiscible solvent is present in the concentration of 0.1% to 40% by weight of total composition.
  • the water immiscible solvent is present in the concentration of 0.1% to 30% by weight of total composition.
  • the antifoaming agents or defoamers which are used in the fungicidal composition of the present invention include but are not limited to one or more of silica, siloxane, silicone dioxide, polydimethyl siloxane, alkyl polyacrylates, ethylene oxide/propylene oxide copolymers, silicone oils and magnesium stearate or derivatives thereof.
  • Preferred antifoaming agents include silicone emulsions (such as, e.g., Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, fluoro-organic compounds.
  • the organic acids include, but not limited to one or more of citric, malic, adipic, fumaric, maleic, succinic, and tartaric acids, or salts, derivatives thereof, and the mono-, di-, or tribasic salts of these acids or derivatives thereof.
  • the salts of inorganic acids include, but not limited to one or more of alkali metal salts such as, sodium chloride, sodium nitrate, potassium nitrate, sodium sulfate, potassium sulfate, sodium monohydrogen phosphate, potassium monohydrogen phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate and the like.
  • pH adjusters or buffers are present in an amount of 0.01% to 20% by weight of the total composition.
  • the anticaking agents which are used in the fungicidal composition include, but are not limited to one or more of polysaccharides, fumed and precipitated silica (white carbon), a petroleum resin, Foammaster® Soap L sodium stearate, Brij® 700 polyoxyethylene (100) stearylether, sodium acetate, sodium metasilicate, sodium alkylsulfosuccinates, or derivatives thereof.
  • the anticaking agent is present in an amount of 0.1% to 20% by weight of the total composition.
  • the spreading agents which are used in the composition include but are not limited to one or more of copolymer of maleic acid with a styrene compound, a (meth)acrylic acid copolymer, aliphatic alcohols, vegetable oils such as cottonseed or inorganic oils, petroleum distillates, trisiloxanes and modified trisiloxanes, or derivatives thereof.
  • the spreading agent is present in an amount of 0.01% to 20% w/w of the total composition.
  • the sticking agents which are used in the composition include, but not limited to one or more of paraffin, a polyamide resin, polyacrylate, polyoxyethylene, wax, latex, polyvinyl pyrrolidone, gums such as xanthan gum, vegetable oils such as cottonseed, or inorganic oils, petroleum distillates, modified trisiloxanes, polyglycol, a synthetic resin emulsion or salts or derivatives thereof.
  • the sticking agent is present in an amount of 0.01% to 30% w/w of the total composition.
  • the structuring agents that are used in the fungicidal composition include, but are not limited to one or more of thickeners, viscosity modifiers, tackifiers, suspension aids, rheological modifiers or anti-settling agents.
  • a structuring agent prevents sedimentation of the active ingredient particles after prolonged storage.
  • Preferred structuring agents include one or more of xanthan gum, aluminium silicate, Hydroxypropyl methylcellulose, carboxymethyl cellulose, methylcellulose, polysaccharide, alkaline earth metal silicate, clays, gelatin, and polyvinyl alcohol.
  • the structuring agent is present in an amount of 0.01% to 20% by weight of the composition.
  • the structuring agent is present in an amount of 0.01% to 10% by weight of the composition.
  • the structuring agent is present in 0.01% to 5% by weight of the composition.
  • the anti-freezing agents or freezing point depressants used in the composition include, but are not limited to one or more of polyhydric alcohols such as ethylene glycol, diethylene glycol, dipropylene glycol, propylene glycol, glycerol, monohydric or polyhydric alcohols, glycol ethers, glycerol,
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, dipropylene glycol, propylene glycol, glycerol, monohydric or polyhydric alcohols, glycol ethers, glycerol.
  • the anti-freezing agents or freezing point depressants is present in an amount of 0.01% to 30% by weight of the total composition.
  • the penetrant which is used in the composition include, but not limited to one or more of alcohol, glycol, glycol ether, ester, amine, alkanolamine, amine oxide, quaternary ammonium compound, triglyceride, fatty acid ester, fatty acid ether, N-methyl pyrrolidone, dimethyl formamide, dimethyl acetamide, or dimethyl sulfoxide, polyoxyethylenetrimethylolpropanemonooleate, polyoxyethylene sorbitan monooleate polyoxyethylenetrimethylolpropanedioleate, polyoxyethylene trimethylol propane trioleate, polyoxyethylene sorbitol hexaoleate.
  • the penetrant is present in an amount of 0.01% to 30% by weight of the total composition.
  • the humectant is selected from, but not limited to one or more of polyoxyethylene/polyoxypropylene copolymers, particularly block copolymers.
  • Other humectants are propylene glycol, monoethylene glycol, hexylene glycol, butylene glycol, ethylene glycol, diethylene glycol, poly (ethylene glycol), poly (propylene glycol), glycerol and the like; polyhydric alcohol compounds such as propylene glycol ether, derivatives thereof.
  • the humectant is present in the range of 0.1% to 40% by weight of the total composition.
  • the stabilizers which are used in the agricultural composition include, but not limited to one or more of peroxide compounds such as hydrogen peroxide and organic peroxides, zeolite, antioxidants such as phenol compounds, phosphoric acid compounds, EDTA, sodium sulphites, citric acid, citrates and the like.
  • peroxide compounds such as hydrogen peroxide and organic peroxides
  • zeolite such as phenol compounds, phosphoric acid compounds, EDTA, sodium sulphites, citric acid, citrates and the like.
  • antioxidants such as phenol compounds, phosphoric acid compounds, EDTA, sodium sulphites, citric acid, citrates and the like.
  • the stabilizer is present in the range of 1% to 30% by weight of the total composition.
  • preservative is selected from one or more of formic acid, and derivatives of 2H isothiazol-3-one (so-called isothiazolone derivatives) such as alkylisothiazolones (for example 2-methyl-2H-isothiazol-3-one, MIT; chloro-2-methyl- 2H-isothiazol-3-one, CIT), benzoisothiazolones (for example 1,2-benzoisothiazol-3(2H)- one, BIT, commercially available as Proxel® types from Arch Biocides Ltd.) or 2-methyl- 4,5-trimethylene-2H-isothiazol-3-one (MTIT), Proxel® from Arch Biocides Ltd.
  • 2H isothiazol-3-one such as alkylisothiazolones (for example 2-methyl-2H-isothiazol-3-one, MIT; chloro-2-methyl-
  • Antioxidants includes but not limited to one or more of imidazole and imidazole derivatives (e.g.
  • the preservative is present in the range of 0.01% to 2% by weight of the total composition.
  • the pigments and colorants are selected from but not limited to synthetic chemicals obtained from various manufacturers.
  • the pigments and colorants can be water soluble or water insoluble, in the form of lakes.
  • Dyes can be solvent dyes, acid dyes or basic dyes. Examples of such products include, but not limited, Unisperse Red 3855, Pigmosol Agro Red 3785, pigment 15.
  • the pigments and colorants are present in the range of 0.01% to 5% by weight of the total composition.
  • the disintegrating agents which are used in the agricultural composition include, but not limited to one or more of inorganic water soluble salts e.g.
  • the disintegrating agent is present in the range of 0.5% to 15% by weight of the total composition.
  • the binding agents or binders that are used in the agricultural composition include, but not limited to one or more of maltodextrin, carbohydrates such as monosaccharides, disaccharides, oligosaccharides and polysaccharides, complex organic substance, synthetic organic polymers or derivatives and combinations thereof.
  • the binder is present in the range of 0.1% to 10% by weight of the total composition.
  • the fungicidal composition includes at least one further active ingredient.
  • the further active ingredients include one or more of pesticidal active ingredients, macronutrients, organic acids, or mixtures thereof.
  • the pesticidal active ingredients is one or more of insecticides, fungicides, herbicides, miticides, acaricides, nematicides, pheromones, algicides, antifeedants, avicides, bactericides, bird repellents, biopesticides, insect repellents, ovicides, rodenticides, etc.
  • insecticides fungicides
  • fungicides herbicides
  • miticides miticides
  • acaricides nematicides
  • pheromones algicides
  • antifeedants avicides
  • bactericides bactericides
  • biopesticides biopesticides
  • insect repellents ovicides
  • rodenticides etc.
  • the fungicidal composition does not include micronutrients or fertilizers as further active ingredients.
  • the fungicidal composition has a viscosity at 25° C. of about 10 cps to about 2000 cps. According to an embodiment, the fungicidal composition has a viscosity at 25° C. of about 10 cps to about 1500 cps. According to an embodiment, the fungicidal composition has a viscosity at 25° C. of about 10 cps to about 1200 cps. According to an embodiment, the fungicidal composition has a viscosity at 25° C. of about 10 cps to about 1000 cps. According to an embodiment, the fungicidal composition has a viscosity at 25° C.
  • the fungicidal composition has a viscosity at 25° C. of about 10 cps to about 500 cps. According to an embodiment, the fungicidal composition has a viscosity at 25° C. of about 10 cps to about 400 cps. According to an embodiment, the fungicidal composition has a viscosity at 25° C. of about 10 cps to about 300 cps. According to an embodiment, the liquid suspension composition of the present invention is easily pourable. The pourability is the measure of percent of residue. According to an embodiment, the pourability of the fungicidal composition is determined as per CIPAC MT-148.1.
  • EXAMPLE 25 Valifenalate 0.1% + Propineb 45% oil dispersion 50 Parts of sodium laureth sulfate were added to 369.4 parts of aliphatic oil and homogenized by feeding them into a vessel provided with stirring facilities, to obtain a mixture. To the mixture obtained, 2 parts of oleic acid, 5 parts of a non-ionic surfactant prepared from reaction of C10 guerbet alcohol and ethylene oxide and 7.5 parts of alkyl polyethylene glycol ether were added and the material was homogenized. Finally, pre- ground technical including 1.1 part of Valifenalate and 565 parts of propineb were added to the homogenized blend and stirred continuously for 30 minutes until the total mixture was homogeneous.
  • composition had a particle size distribution as follows: D10: 1.8 microns; D50: 5.2 microns and D90: 7.2 microns, viscosity of 540 cps and a suspensibility of 79%.
  • the pourability rinsed residue was found to be 0.55%.
  • the composition exhibited a suspensibility of 75% under accelerated storage conditions.
  • EXAMPLE 26 Valifenalate 15% + Propineb 1% oil dispersion 10 Parts of alcohol ethoxylate were added to 790 parts of homogenized by feeding them into a vessel provided with stirring facilities. To the above mixture, 20 parts of alkyl polyethylene glycol ether were added and the material was homogenized.
  • the composition had a particle size distribution of D10: 1.3 microns; D50: 3.8 microns and D90: 7.2 microns, viscosity of 380 cps and a suspensibility of 76%.
  • the composition exhibited a suspensibility of 72% under accelerated storage conditions.
  • the composition had a particle size distribution as follows: D10: 1.1 microns; D50: 3.2 microns and D905.6 microns, viscosity of 472 cps and a suspensibility of 82%.
  • the composition exhibited a suspensibility of 78% under accelerated storage conditions.
  • the percentage disease reduction with the treatments T1 and T2 is also higher than the expected percentage disease reduction calculated by Colby’s method i.e. 57.3%.
  • the treatments T1 and T2 with the compositions as per the present invention demonstrated a synergistic effect compared to the application with individual actives i.e. treatments T3 and T4.
  • the compositions of Treatments T1 and T2 (based on the embodiments of the present invention) showed a 26.3% and 25.6%, increase in the yield of tomato, respectively, over the untreated control, as compared to the treatments T3 and T4 which only showed a yield increase of 9.1% and 11.4%, respectively, over the untreated control.
  • the yield with the Treatment T1 is higher than the expected yield of 19.5%.
  • Table 1B Table 1B:
  • the yield with the Treatment T1 is higher than the expected yield of 5.7%.
  • the enhancement in efficacy with the compositions, as per the present invention, as can be seen from the Tables 1A and 1B is surprising, as the dosages of Valifenalate and Metiram, applied in the individual treatments and in the compositions, as per the present invention are the same.
  • compositions as per the embodiment of the present invention can be attributed to the composition of Valifenalate and Metiram, where both the actives are present in a single composition in specific concentration and where the water dispersible granular composition includes particles in the size range of 0.1 micron to 50 microns and the liquid suspension composition includes particles in a size range of 0.1 micron to 30 microns.
  • Field trial 2 To study the effect of valifenalate and metiram or propineb for controlling late blight infestation in tomato. The field trials were carried out to study the effect of the composition of valifenalate and metiram or propineb, in tomato in Akola, Maharashtra. The trial was laid out during the Rabi season i.e.
  • the yield with the Treatments T1 and T2 is higher than the expected yield of 8.3%. Furthermore, it can be observed from table 2A that the Treatments T3 and T4, both as per the embodiments of the present invention, where the actives are applied at a reduced dosage as compared to the stand alone actives or as compared to the dosage applied in Treatments T1 or T2 also demonstrated a 78.56% and 76.76% disease control, respectively, and an enhanced yield, over the untreated control or as compared to the treatments T3 and T4 with individual actives. applied at higher dosages.
  • Table 2B Treat Composition Active ingredient % Late % Control at Yield in % Yield ment Blig 20 days after kg/ha increase No.
  • Control (%) [Damage in control plot –Damage in treated plot) /Damage in control plot]
  • X 100 Synergy factor was computed using the formula discussed in Field Trial – Experiment 1. The mean data on control against the downy mildew infestation along with the crop yield was recorded at harvest and is presented in the Table 3A: Table 3A:
  • PDI over incidence control
  • the yield with the Treatments T1 and T2 is higher than the expected yield of 17.4%.
  • the enhancement in efficacy with the composition as per the present invention is surprising, as the dosages of Valifenalate and Propineb, applied in the individual treatments and in the compositions as per the present invention, are the same.
  • the surprising synergistic results observed with the compositions as per the embodiment of the present invention as seen in Tables 3A and 3B are attributed to the composition of Valifenalate and Propineb, where both the actives are present in a single composition, in specific concentrations and where the composition includes particles in a specific size range as per the embodiment of the present invention.
  • Field trial 4 To study effect of valifenalate and propineb or metiram for controlling downy mildew infestation in grapes.
  • the field trials were carried out to study the effect of the composition of valifenalate and propineb in grapes, in Sangli, Maharashtra.
  • the trial was laid out during Rabi season i.e. October to January in Randomized Block Design (RBD) with ten treatments including untreated control, replicated five times, applied in two different plots.
  • RBD Randomized Block Design
  • the test product samples, valifenalate and propineb or metiram, alone and in combination with prescribed dose were applied as foliar application after planting of grape seedlings in the trial plot.
  • the grape crop in the trial field was raised following good agricultural practices.
  • Control (%) [Damage in control plot –Damage in treated plot) /Damage in control plot] X 100 Synergy factor was computed using the formula discussed in Field Trial – Experiment 1. The mean data on control against the downy mildew infestation along with the crop yield was recorded at harvest and is presented in the Table 4A: Table 4A: Treat Composition Active ingredient % downy % Control at Yield in % Yield ment mild 10 DA2S kg/ha increase No.
  • percentage disease reduction with the treatment T1 is also higher than the expected percentage disease reduction calculated by Colby’s method i.e.45.3%.
  • the treatment T1 with the composition as per the present invention demonstrated a synergistic effect compared to the application with individual actives i.e. treatments T3 and T4.
  • the composition of Treatment T1 (based on the embodiment of the present invention) showed a 20.7%, increase in the yield of grapes over the untreated control, as compared to the treatments T2 and T3, which only showed a yield increase of 8.3% and 6.2%, respectively, over the untreated control.
  • the yield with the Treatment T1 is higher than the expected yield of 14%.
  • percentage disease reduction with the treatment T1 is also higher than the expected percentage disease reduction calculated by Colby’s method i.e.72.6%.
  • the treatment T1 with the composition as per the embodiment of the present invention demonstrated a synergistic effect compared to the application with individual actives i.e. treatments T3 and T4.
  • the composition of Treatment T1 (based on the embodiment of the present invention) showed a 16.3%, increase in the yield of grapes over the untreated control, as compared to the treatments T2 and T3, which only showed a yield increase of 3.9% and 9.2%, respectively, over the untreated control.
  • the yield with the Treatment T1 is higher than the expected yield of 12.7%.
  • Randomized Block Design (RBD) with seven treatments including untreated control, replicated five times.
  • the test product samples, valifenalate and propineb or metiram, in combination with prescribed dose and varying particle size ranges were applied as foliar application after planting of potato in the trial plot.
  • the potato crop in the trial field was raised following good agricultural practices.
  • the tubers were planted in 60 cms row to row and 25 cms plant to plant spacing.
  • Control (%) [Damage in control plot –Damage in treated plot) /Damage in control plot] X 100 Synergy factor was computed using the formula discussed in Field Trial – Experiment 1. The mean data on control against the Phytophthora infestans incidence along with the crop yield was recorded at harvest and is presented in the Table 5 to enumerate the impact of the composition comprising valifenalate and metiram or propineb with specific particle size as compared to the compositions with the higher particle size ranges.
  • composition of Treatments T1 and T4 (as per the present invention) showed a 16.9% and 16.1% increase, in the yield of potatoes over the untreated control, as compared to the treatments T2, T3, T5 and T7, which only showed a yield increase of 8.8%, 5.5%, 6.1% and 3.3%, respectively, over the untreated control.
  • the results are all the more surprising as the dosages of the actives applied i.e Valifenalate and Metiram or propineb, applied in each of the treatments are the same.
  • the surprising results can be attributed to the form of the composition i.e.
  • Field trial 6 To study effect of valifenalate and metiram for controlling early blight infestation in potatoes. The field trials were carried out to study the effect of the composition of valifenalate and metiram, with varying particle sizes in potato. The trial was laid out during the Rabi season i.e. October to January in Randomized Block Design (RBD) with seven treatments including untreated control, replicated five times.
  • RBD Randomized Block Design

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Abstract

La présente invention concerne une composition fongicide comprenant du valifénalate ou des sels acceptables en agriculture de celui-ci dans la plage de 0,1 % p/p à 50 % p/p de la composition totale ; un composé dithiocarbamate choisi parmi le propinèbe et le métirame ou leurs sels acceptables en agriculture, le composé dithiocarbamate étant présent dans la plage de 0,1 % p/p à 70 % p/p de la composition totale ; et au moins un excipient agrochimiquement acceptable ; la composition comprenant des particules dans la plage de taille de 0,1 micron à 50 microns. L'invention concerne en outre un procédé de préparation de la composition fongicide et un procédé de traitement d'une plante, d'un matériel de propagation de plante, d'un locus ou de parties de plante associés, d'une graine, d'un semis ou d'un sol environnant avec la composition fongicide.
PCT/IN2024/051670 2023-09-06 2024-09-06 Composition fongicide comprenant du valifénalate et du dithiocarbamate Pending WO2025052473A1 (fr)

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IN202321060350 2023-09-06

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019186359A1 (fr) * 2018-03-26 2019-10-03 Upl Ltd Associations fongicides
WO2020261030A1 (fr) * 2019-06-24 2020-12-30 Upl Limited Composition fongicide synergique

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019186359A1 (fr) * 2018-03-26 2019-10-03 Upl Ltd Associations fongicides
WO2020261030A1 (fr) * 2019-06-24 2020-12-30 Upl Limited Composition fongicide synergique

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