WO2018206253A1 - Pesticide compositions - Google Patents

Pesticide compositions Download PDF

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Publication number
WO2018206253A1
WO2018206253A1 PCT/EP2018/060030 EP2018060030W WO2018206253A1 WO 2018206253 A1 WO2018206253 A1 WO 2018206253A1 EP 2018060030 W EP2018060030 W EP 2018060030W WO 2018206253 A1 WO2018206253 A1 WO 2018206253A1
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Prior art keywords
composition
seed
weight
seeds
concentration
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PCT/EP2018/060030
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French (fr)
Inventor
Doreen Evans HEATH
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Syngenta Participations AG
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Syngenta Participations AG
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Priority to JP2019561835A priority Critical patent/JP7488048B2/en
Publication of WO2018206253A1 publication Critical patent/WO2018206253A1/en
Anticipated expiration legal-status Critical
Priority to JP2022120228A priority patent/JP7504165B2/en
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    • 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests

Definitions

  • the present technology relates to seed treatments, and in particular seed treatment compositions that have improvements in drying times and plantability.
  • Pesticides can be applied directly to plant propagation materials (such as seeds) prior to sowing and/or are used in foliar or furrow applications.
  • a seed treatment is any material applied to a seed.
  • seed treatments include, inter alia, pesticides, non-pesticide formularies, and mixtures thereof.
  • Non-pesticide formularies generally include material such as surfactants, humectants, fillers, and polymers that influence the treated seed characteristics.
  • Seed treatments are generally used on a variety of crops to control a variety of pests. Seed treatments are commonly used to ensure uniform stand establishment by protecting against soilborne diseases and insects. Systemic seed treatments may provide an alternative to traditional broadcast sprays of foliar fungicides or insecticides for certain early season airborne diseases and insects.
  • Pesticide seed treatments come in a variety of formulations: dry flowables (DF), liquid flowables (LF), true liquids (TL), emulsifiable concentrates (EC), dusts (D), wettable powders (WP), suspoemulsions (SE), water-dispersible granules (WG) and others. Some are registered for use only by commercial applicators using closed application systems, others are readily available for on-farm use as dusts, slurries, water soluble bags, or liquid ready-to-apply formulations.
  • DF dry flowables
  • LF liquid flowables
  • TL true liquids
  • EC emulsifiable concentrates
  • D dusts
  • WP wettable powders
  • SE suspoemulsions
  • WG water-dispersible granules
  • Seed coating additives are seed treatments used to remedy problems such as low seed flowability and excessive dust-off.
  • selection of a seed coating additive to reduce dust-off will likely have the adverse effect of decreasing seed flowability.
  • selection of a seed coating to increase seed flowability will likely have the adverse effect of increasing dust-off.
  • the present technology provides for seed treatment compositions having improved adherence to plant propagation material with low dust-off.
  • the compositions of the present technology have particular application in the protection of plant propagation materials, such as seeds, against pests when combined with one or more pesticides.
  • the present technology thus provides an improved seed treatment suitable for applying to plant propagation materials.
  • the seed treatments of the present technology include propylene glycol and talc. Such additions drastically improve the drying time of the seed treatment compositions, thereby improving the adherence to the seed.
  • FIG. 1 is a chart providing the results of Example 2.
  • Propylene glycol also called propane- 1,2-diol
  • propane- 1,2-diol has the chemical formula C3H8O2.
  • the use of propylene glycol in the compositions of the present invention aid in the drying times of the composition after it has been used to treat seeds.
  • propylene glycol is sometimes utilized in seed treatment formulations, it is done so for its properties as an antifreeze component and not as a component for reducing drying times.
  • the amount of propylene glycol in the composition may be between about 2% and about 8% by weight of the composition.
  • the amount of propylene glycol in the composition may be between about 4% and about 6% by weight of the composition.
  • the amount of propylene glycol in the composition may be about 5% by weight of the composition.
  • talc is utilized to aid in the drying times of the compositions of the present invention.
  • certain amounts of talc may be necessary to ensure that the compositions of the present invention do not result in too much dust-off, forcing the composition off of the seed after treating.
  • talc is utilized in the composition in an amount less than or equal to about 10% by weight of the composition.
  • talc is utilized in the composition in an amount less than or equal to about 9% by weight of the composition, or an amount less than or equal to about
  • Talc suitable for the present invention may include SILVERLINE 002 (magnesium silicate) (Fitz Chem of Itasca, IL) and SILVERLINE 202 (magnesium silicate) (Imerys Corporation of Sylacauga, AL).
  • the talc may include magnesium silicate.
  • the propylene glycol and talc utilized in the compsositions of the present invention may also be expressed in the form of a ratio.
  • the ratio of propylene glycol to talc may be from about 2: l to about 1 :2, from about 1.5:1 to about 1 : 1.5, from about 1.2: 1 to about 1 :1.2 all by weight of the composition.
  • the propylene glycol to talc may be about 1 :1 ratio by weight of the composition.
  • compositions of the present invention may reduce drying times of the compositions once applied to seeds to less than 5 hours.
  • compositions of the present invention may reduce drying times of the composition once applied to seeds to less than 2 hours.
  • Seed treatment formulations applied to seeds generally comprise a pesticide, surfactants, film- forming polymers, carriers, antifreeze agents, and other formulary additives and when used together provide compositions that are storage stable and are suitable for use in normal seed treatment equipment, such as a slurry seed treater, direct treater, panogen treater or a mist-o-matic treater as well as on-farm hopper-box or planter-box treatments. Propagation materials treated with the compositions dry quickly, have good flowability, suitable coverage and have little or no dust-off.
  • the compositions are advantageously combined with a pesticidally effective amount of at least one pesticide.
  • Pesticides are intended to cover compounds active against pests which are intended to repel, kill, or control any species designated a pest including weeds, insects, rodents, fungi, bacteria, or other organisms.
  • pesticides include those selected from, for example and not for limitation, insecticides, acaricides, bactericides, fungicides, nematicides and molluscicides.
  • Suitable additions of insecticidally, acaricidally, nematicidally, or molluscicidally active ingredients are, for example and not for limitation, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenols and derivatives, formamidines, triazine derivatives, nitroenamine derivatives, nitro- and cyanoguanidine derivatives, ureas, benzoylureas, carbamates, pyrethroids, chlorinated hydrocarbons and Bacillus thuringiensis products.
  • the insecticides may include thiamethoxam, abamectin, cyanoimine, acetamiprid, thiodicarb, nitromethylene, nitenpyram, clothianidin, dinotefuran, fipronil, lufenuron, pyripfoxyfen, thiacloprid, fluxofenime; imidacloprid, Chloranthraniliprole, beta cyfiuthrin, lambda cyhalothrin, fenoxycarb, diafenthiuron, pymetrozine, diazinon, disulphoton; profenofos, furathiocarb, cyromazin, cypermethrin, tau-fiuvalinate, spinetoram, spinosad, sulfloxaflor, tefiuthrin or Bacillus thuringiensis products.
  • Suitable additions of fungicidally active ingredients are, for example and not for limitation, representatives of the following classes of active ingredients: strobilurins, triazoles, ortho-cyclopropyl-carboxanilide derivatives, phenylpyrroles, and systemic fungicides.
  • fungicidally active ingredients include, but are not limited to, the following compounds: azoxystrobin; bitertanol; carboxin; Cu 2 0; cymoxanil;
  • cyproconazole cyprodinil; dichlofluamid; difenoconazole; diniconazole; epoxiconazole;
  • fenpiclonil fludioxonil; fiuoxastrobin, fluquiconazole; fiusilazole; flutriafol; furalaxyl;
  • guazatin hexaconazole; hymexazol; imazalil; imibenconazole; ipconazole; kresoxim-methyl; mancozeb; metalaxyl; mefenoxam; metconazole; myclobutanil, oxadixyl, pefurazoate;
  • the pesticides of the present composition may include thiamethoxam, mefenoxam and fludioxonil.
  • the pesticidally active compound or compound mixture is present in the composition in an amount of from about 0.05 % to about 50 % by weight, more specifically, from 2 to about 30% by weight of the entire composition.
  • the pesticidally active compounds include between about 20 and 30% by weight of the composition.
  • Seed treatment application rates with respect to pesticidally active ingredients may be between about 0.5 to 1000 g of pesticidally active compound per 100 kg seed.
  • application rate ranges with respect to seed treatments include: 0.5 to 500 g of pesticidally active compound per 100 kg seed; 0.5 to 250 g of pesticidally active compound per 100 kg seed; 0.5 to 100 g of pesticidally active compound per 100 kg seed; 0.5 to 75 g of pesticidally active compound per 100 kg seed; and 0.5 to 55 g of pesticidally active compound per 100 kg seed.
  • Seed treatment compositions may also contain at least about 2% up to about 15% by weight of a surface-active agent.
  • Compositions may contain from 3% up to 7% by weight of a surface -active agent.
  • the surface-active agent may comprise at least one nonionic surfactant and may optionally further comprise one or more anionic surfactants.
  • nonionic surfactants include polyarylphenol polyethoxy ethers, polyalkylphenol polyethoxy ethers, polyglycol ether derivatives of saturated fatty acids, polyglycol ether derivatives of unsaturated fatty acids, polyglycol ether derivatives of aliphatic alcohols, polyglycol ether derivatives of cycloaliphatic alcohols, fatty acid esters of polyoxy ethylene sorbitan, alkoxylated vegetable oils, alkoxylated acetylenic diols, polyalkoxylated alkylphenols, fatty acid alkoxylates, sorbitan alkoxylates, sorbitol esters, C 8 - C22 alkyl or alkenyl polyglycosides, polyalkoxy styrylaryl ethers, alkylamine oxides, block copolymer ethers, polyalkoxylated fatty glyceride, polyalkylene glycol ethers
  • nonionic sufactants include: Genapol X-060 (Clariant) (ethoxylated fatty alcohol); Sorpohor BSU (Rhodia) (ethoxylated tristyrylphenol); Makon TD- 6 (Stepan) (ethoxylated fatty alcohol); BRIJ 30 (Uniqema) (ethoxylated lauryl alcohol);
  • Witconol CO-360 (Witco) (ethoxylated castor oil)
  • Toximul 8320 (Stepan) (polyethylene- polypropylene glycol monobutyl ether); and Witconol NP-60 (Witco) (ethoxylated
  • nonylphenol nonylphenol
  • Suitable nonionic surfactants can be prepared by methods known per se and also are commercially available.
  • the anionic surfactant may be any known in the art.
  • Anionic surfactants are in general oligomers and polymers, as well as polycondensates, which contain a sufficient number of anionic groups to ensure their water-solubility.
  • Anionic surfactants also include alcohol sulfates, alcohol ether sulfates, alkylaryl ether sulfates, alkylaryl sulfonates such as alkylbenzene sulfonates and alkylnaphthalene sulfonates and salts thereof, alkyl sulfonates, mono- or di-phosphate esters of polyalkoxylated alkyl alcohols or alkylphenols , mono- or di- sulfosuccinate esters of C12-C15 alkanols or polyalkoxylated C12-C15 alkanols, alcohol ether carboxylates, phenolic ether carboxylates, polybasic acid esters of ethoxylated polyoxyalkylene glycols consisting of oxybutylene or the residue of tetrahydrofuran, sulfoalkylamides and salts thereof such as N-methyl ⁇ N-oleoyltaurate Na
  • anionic surfactants include: Geropon T77 (Rhodia) (N- methyl--N-oleoyltaurate Na salt); Soprophor 4D384 (Rhodia) (tristyrylphenol sulphate); Reax 825 (Westvaco) (ethoxylated lignin sulfonate); Stepfac 8171 (Stepan) (ethoxylated
  • nonylphenol phosphate ester nonylphenol phosphate ester
  • Stepfac 8181 (tridecyl alcohol ethoxy late phosphate ester), Ninate 401-A (Stepan) (calcium alkylbenzene sulfonate); Emphos CS-131 (Witco) (ethoxylated nonylphenol phosphate ester); Ultrazine NA (sodium lignosulfonate); Ufoxane 3A, NA (sodium lignosulphonate); Morwet D-425 (sodium alkylnapthalenesulfonate), Reax 1425E (lignin sulfonate ethoxylate), and Atphos 3226 (Uniqema) (ethoxylated tridecylalcohol phosphate ester).
  • Suitable anionic surfactants can be prepared by methods known per se and also are commercially available.
  • certain cationic or zwitterionic surfactants also are suitable for use in the present invention such as alkanol amides of Cs-Cis fatty acids and Cs-Cis fatty amine polyalkoxylates, Cio-Cis alkyldimethylbenzylammonium chlorides, coconut alkyldimethylaminoacetic acids, and phosphate esters of Cs-is fatty amine polyalkoxylates.
  • zwitterionic surfactants may be employed as follows: (1) 0.5 - 4% by weight of a wetting agent selected from at least one anionic surfactant.
  • Anionic surfactant wetting agents include sulfoalkylamides and salts thereof such as N-methyl ⁇ N-oleoyltaurate Na salt, alkylaryl sulfonates such as alkylbenzene sulfonates and alkylnaphthalene sulfonates and salts thereof and salts of ligninsulfonic acid; (2) 1 - 4% by weight of a dispersing agent selected from at least one anionic surfactant.
  • Anionic surfactant dispersing agents include sulfate esters of styrylphenyl alkoxylates, and sulfonate esters of styrylphenyl alkoxylates and their
  • compositions may contain between about 1.5 and about 8 % by weight of surface active agents.
  • the compositions of the present invention may include about 1 to about 3 % by weight of an anionic surfactant and from about 0.5 to about 3 % by weight of a nonionic surfactant.
  • the anionic surfactant may be tridecyl alcohol ethoxylate phosphate ester and the nonionic surfactant may be polyethylene -polypropylene glycol monobutyl ether.
  • the compositions of the present invention may include about 1% by weight of the nonionic surfactant and may also include about 2% by weight of an anionic surfactant.
  • the composition may include the Morwet D-425 (sodium alkylnapthalenesulfonate) at about 0.2% by weight of the composition, Ultrazine NA (sodium lignosulfonate) at about 2.0% by weight of the composition, Stepfac 8181 (tridecyl alcohol ethoxylate phosphate ester) at about 2.0% by weight of the composition, Toximul 8320 (polyethylene -polypropylene glycol monobutyl ether) at about 1 .0% by weight of the composition, propylene glycol at about 5.0% by weight of the composition, and Silverline 002 (magnesium silicate) at about 5.0% by weight of the composition or at about 10.0% by weight of the composition.
  • Morwet D-425 sodium alkylnapthalenesulfonate
  • Ultrazine NA sodium lignosulfonate
  • Stepfac 8181 tridecyl alcohol ethoxylate phosphate ester
  • Toximul 8320 poly
  • Seed treatment compositions may also include a humectant.
  • a humectant is hygroscopic substance used to retain water.
  • the compositions generally contain from 1% to 30 % by weight of the composition.
  • commonly used formulation humectants include antifreezes, for example ethylene glycol, propylene glycol and glycerin. In examples where propylene glycol is utilized as a humectant the amount expressed above is in addition to the other amounts provided.
  • Film-forming Polymer [0038] Seed treatment composition may also include at least one polymer selected from water-soluble and water-dispersible film-forming polymers.
  • Suitable polymers generally have an average molecular weight of at least about 1 ,000 up to about 100,000; more specifically at least about 5,000, up to about 100,000.
  • the compositions generally contain from about 0.5% to about 10% by weight of the composition of polymer. In a specific embodiment, the compositions contain from about 1.0% up to about 5% by weight of a film- forming polymer.
  • Polymers are generally selected from alkyleneoxide random and block copolymers such as ethylene oxide -propylene oxide block copolymers (EO/PO block copolymers) including both EO-PO-EO and PO-EO-PO block copolymers, ethylene oxide -butylene oxide random and block copolymers, C2-6 alkyl adducts of ethylene oxide -propylene oxide random and block copolymers, C2-6 alkyl adducts of ethylene oxide -butylene oxide random and block copolymers.
  • alkyleneoxide random and block copolymers such as ethylene oxide -propylene oxide block copolymers (EO/PO block copolymers) including both EO-PO-EO and PO-EO-PO block copolymers, ethylene oxide -butylene oxide random and block copolymers, C2-6 alkyl adducts of ethylene oxide -propylene oxide random and block copolymers.
  • Prospective polymers further include polyoxyethylene-polyoxypropylene monoalkylethers such as methyl ether, ethyl ether, propyl ether, butyl ether or mixtures thereof; vinylacetate/vinylpyrrolidone copolymers; alkylated vinylpyrrolidone copolymers;
  • polyvinylpyrrolidone and polyalkyleneglycol including the polypropylene glycols and polyethylene glycols.
  • polymers include Pluronic PI 03 (BASF) (EO-PO-EO block copolymer), Pluronic P65 (BASF) (EO-PO-EO block copolymer), Pluronic PI 08 (BASF) (EO- PO-EO block copolymer), Vinamul 18160 (National Starch) (polyvinylacetate), Agrimer 30 (ISP) (polyvinylpyrrolidone), Agrimer VA7w (ISP) (vinyl acetate/vinylpyrrolidone
  • compositions and methods lack a film- forming polymer that are provided above. As illustrated in the Examples provided below, the absence of such a film-forming polymer may aid in plantability of the composition. [0042] Antifreeze
  • composition may also comprise an antifreeze from about 2 and up to about 30% by weight.
  • antifreezes include ethylene glycol, 1,2 -propylene glycol, 1,3- propylene glycol, 1,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 1 ,4-pentanediol, 3-methyl- 1,5-pentanediol, 2,3-dimethyl-2,3-butanediol, trimethylol propane, mannitol, sorbitol, glycerol, pentaerythritol, 1,4-cyclohexanedimethanol, xylenol, bisphenols such as bisphenol A or the like.
  • ether alcohols such as diethylene glycol, triethylene glycol, tetraethylene glycol, polyoxyethylene or polyoxypropylene glycols of molecular weight up to about 4000, diethylene glycol monomethylether, diethylene glycol monoethylether, triethylene glycol monomethylether, butoxyethanol, butylene glycol monobutylether, dipentaerythritol, tripentaerythritol, tetrapentaerythritol, diglycerol, triglycerol, tetraglycerol, pentaglycerol, hexaglycerol, heptaglycerol, octaglycerol and the like.
  • ethylene glycol propylene glycol
  • glycerin ethylene glycol
  • propylene glycol the amount expressed above is in addition to the other amounts provided.
  • the composition may also contain (e) at least one thickener.
  • the thickener is present in the aqueous composition in an amount from about 0.01% to about 25% by weight, more specifically from 0.02 to 10% by weight of the entire composition.
  • thickeners water-soluble polymers which exhibit pseudoplastic properties in an aqueous medium
  • gum arabic gum karaya
  • gum tragacanth gum tragacanth
  • guar gum locust bean gum
  • xanthan gum carrageenan
  • alginate salt casein, dextran, pectin, agar
  • 2- hydroxyethyl starch 2-aminoethyl starch
  • 2 -hydroxy ethyl cellulose methyl cellulose, carboxymethyl cellulose salt, cellulose sulfate salt
  • polyacrylamide alkali metal salts of the maleic anhydride copolymers, alkali metal salts of poly(meth)acrylate, and the like.
  • Attapulgite-type clay carrageenan, croscarmellose sodium, furcelleran, glycerol, hydroxypropyl methylcellulose, polystyrene, vinylpyrrolidone/styrene block copolymer, hydroxypropyl cellulose,
  • composition according to the invention can be employed together with the adjuvants customary in formulation technology, biocides, biostats, emulsifiers (lethicin, sorbitan, and the like), antifoam agents or application-promoting adjuvants customarily employed in the art of formulation.
  • adjuvants customary in formulation technology
  • biocides biostats
  • emulsifiers lethicin, sorbitan, and the like
  • antifoam agents customarily employed in the art of formulation.
  • inoculants and brighteners there may be mentioned inoculants and brighteners.
  • a coloring agent such as a dye or pigment (and the like such as described in the CFR 180.1001) is included in the seed coating so that an observer can immediately determine that the seeds are treated.
  • the dye is also useful to indicate to the user the degree of uniformity of the coating applied.
  • inventive compositions contain and/or may be applied together or sequentially with further active compounds.
  • further compounds can be fertilizers or micronutrient donors or other preparations that influence plant growth. They can also be selective herbicides, insecticides, fungicides, bactericides, insect growth regulators, plant growth regulators, nematicides, molluscicides or mixtures of several of these preparations.
  • the pesticidal compositions of the invention can be prepared by processes known in the art.
  • the compositions of the invention can be prepared by a process which comprises the steps: (a) forming a premix with at least one pesticidal compound, at least one surfactant, and water (b) forming a premix of a thickener and water, and (c) sequentially adding the premixes (a) and (b), talc, propylene glycol, the remaining ingredients, and water while stirring to form a homogeneous composition.
  • compositions of the invention can be prepared by combining commercially available seed treatment formulations with talc and propylene glycol.
  • Pesticidal compositions in accordance with the invention may take the form of aqueous solutions, dispersions, suspensions, emulsions or suspoemulsions.
  • aqueous solutions dispersions, suspensions, emulsions or suspoemulsions.
  • the composition is a ready for use suspension or suspoemulsion.
  • plant propagation material and seed encompass both true seeds and other types of plant propagation material from which plants grow. Plant propagation material itself is commonly referred to as a seed and is defined as such herein. Many seed treatments are applied to true seeds, which have a seed coat surrounding an embryo. Seed treatments are also applied to plant propagation materials such as rhizomes, bulbs, corms or tubers.
  • the amount of fungicide, insecticide or other ingredients used in the seed treatment are employed in amounts that do not inhibit generation of the seed or cause phytotoxic damage to the seed.
  • the total amount of active ingredients is generally in the range of from about 0.05 % to about 50 % by weight, more specifically, from 15 to about 28% by weight of the entire composition.
  • Suitable target seeds are especially those of corn, potatoes, cereals, (wheat, barley, rye, oats, rice), maize, sugar beet, cotton, millet varieties such as sorghum, sun flowers, beans, peas, oil plants such as canola, rape, soybeans, cabbages, tomatoes, eggplants (aubergines), pepper and other vegetables and spices as well as ornamental shrubs and flowers.
  • Suitable target seeds also include those of transgenic crop plants of the foregoing varieties.
  • Suitable application rates of talc and propylene glycol to plant seeds is between 0.05 to 10.0 g/500g seed; 0.1 to 5.0 g/500g seed; 0.1 to 2.5 g/500g seed; 0.1 to 1.0 g/500g seed; and also between 0.25 to 1.0 g/500 g seed.
  • compositions of the invention are applied to the seed as slurry or a soak. There also may be mentioned, e.g., film coating or encapsulation.
  • the coating processes are well known in the art, and employ, for seeds, the techniques of film coating or encapsulation, or for the other multiplication products, the techniques of immersion.
  • the method of application of the inventive compositions to the seed may be varied and the technology is intended to include any technique that is to be used.
  • the compositions of the present technology may be formulated or mixed in the seed treater tank or combined on the seed by overcoating with other seed treating agents.
  • the agents to be mixed with the compounds of this invention may be for the control of pests, nutrition, and the control of plant diseases.
  • a feature of the technology is that it provides for a treated seed with a reduction in drying times over conventional seed treatments while at the same time reducing excess dust. Accordingly, the formulation aids in reducing the associated health hazards to those who work with treated seeds, such as processing plant employees, truck drivers, warehouse workers, and farmers.
  • Still another feature of the technology is the uniform coating of-seeds with non- dusting seed treatment which will not interfere with germination and sprouting of the seed but which will protect the seed against seed-borne pathogens.
  • each formulation included thiamethoxam (22.62 % by weight), fludioxonil (1.12 % by weight), and mefenoxam (1.70 % by weight).
  • Formulation B also included propylene glycol (5.0 % by weight)
  • Formulation C included propylene glycol (5.0 % by weight) and talc (Silverline 002 5.0 % by weight).
  • Coating Evaluation - On Film Each of the formulations prior to being applied to seeds were placed on a plastic film and allowed to dry. The drying times of each formulation are provided in the Table below.
  • Formulation B Dry to the touch within 1 day
  • Formulation C Dry to the touch within 2 hours
  • Soybean seeds were then treated with each of the three different formulations (A, B, and C) to measure wet flow (g/sec), and dry flow (g/sec).
  • Wet flow Measurement Seeds are taken immediately from the treater and are weighed. The seeds are then placed in a Cox funnel having a 1 .25 inch opening at the stem. The funnel door is opened and a stopwatch concurrently started. The funnel may be tapped lightly if seeds begin to clump. The stopwatch is stopped when the last seed flows from the funnel. The seeds are poured back into the funnel two times and the above procedure repeated for a total of three measurements. The flow measurements are then calculated and averaged.
  • Dry flow Measurement Seeds are taken from the treater and allowed to dry completely (approximately 24 hours) and are then weighed. The seeds are then placed in a Cox funnel having a 1.25 inch opening at the stem. The funnel door is opened and a stopwatch concurrently started. The funnel may be tapped lightly if seeds begin to clump. The stopwatch is stopped when the last seed flows from the funnel. The seeds are poured back into the funnel two times and the above procedure repeated for a total of three measurements. The flow measurements are then calculated and averaged.
  • compositions (A, B, C, D and E shown in Table 3) were prepared and treated onto soybean seeds, and tested under various conditions to determine the plantability of the seed against untreated soybean seeds.
  • the four different compositions were treated on soybean seeds of the variety Waseguro. Once the seeds were treated with the appropriate composition, they were immediately placed in a plastic container. The seeds were then stored at various temperatures and different relative humidity (RH) and were allowed to dry at different intervals.
  • RH relative humidity
  • the drying times and conditions are provided: (1) seeds stored at 25 °C with RH of 60-70% for 30 mins; (2) seeds stored at 25°C with RH of 60-70% for 3 hours; (3) seeds stored at 25°C with RH of 60-70% for 24 hours; (4) seeds stored at 40°C with RH of 98% for 1 hour; and (5) seeds stored at 40°C with RH of 98% for 4 hours.
  • the seeds were placed in a roll-type seeder, which was run for two minutes and the discharged seeds were collected. The weight of the discharged seeds were recorded and each test was repeated three times. Each test was repeated three times (any seeds trapped in the holes were removed after each test). The machine was cleaned after evaluation of each sample and verified to be clean by running the test with untreated seeds in between samples.
  • Cruiser FS30 was included as a standard, because this is known to have good plantability
  • Toximul 8320 1.00 1.00 1.00 1.00 1.00 1.00 1.00
  • a falling seed weight less than 100% indicates impaired plantability compared with untreated seeds.
  • formulations A to E of the present invention all give better plantability compared with the CruiserMaxx or Cruiser FS30 commercial standards, especially under high humidity conditions.
  • Treatments without binder showed better plantability after 30 minutes drying in comparison with treatments containing the binder (formulations D and E); the presence of a film- forming polymer may inhibit flowability of seeds at certain temperatures and relative humidity. Such finding is of immense importance, as many seeds are planted under very hot and humid conditions.
  • CruiserMaxx seed treatment does not contain propylene glycol or talc.
  • Table 5 Dust-off and drying time of treated seeds CruiserMaxx (standard) 0.1 mg Remained wet/tacky after 2 weeks
  • Dust-off levels were similar for all formulations, and all within acceptable levels for seed treatment formulations.
  • the addition of propylene glycol was found to dramatically speed up drying time compared with glycerine in the CruiserMaxx standard. Further, the addition of 5% talc dramatically accelerated drying time without causing dust-off issues. The addition of 10% talc did not further improve drying time. The presence or absence of a binder has little effect on drying time but does marginally improve dusting properties.
  • an FT4 instrument was used to measure the resistance of seeds to flow while the seeds are in motion.
  • a precision 'blade', or impeller is rotated and moved downwards and upwards through the sample to establish a precise flow pattern.
  • This causes many particles/seeds to interact, or flow relative to one another, and the resistance experienced by the blade represents the difficulty of this relative particle movement, or the bulk flow properties.
  • This resistance is measured as the force required to move the seeds and presented as Down Energy or Up Energy. The less force, the better the flow properties of a treated seed. Resistance to flow can create issues with seed handling and plantability. Good flow properties related to the tackiness of the seeds not only immediately after treatment but after the drying process.

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  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
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  • Pest Control & Pesticides (AREA)
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Abstract

A composition for treating seeds that includes talc and propylene glycol to reduce drying times of the composition once applied to the seed.

Description

PESTICIDE COMPOSITIONS
TECHNICAL FIELD
[0001] The present technology relates to seed treatments, and in particular seed treatment compositions that have improvements in drying times and plantability.
BACKGROUND
[0002] The use of pesticides to control pests in crops is a wide spread practice. This practice has gained a high degree of commercial success because it has been shown that such control can increase crop yield. Pesticides can be applied directly to plant propagation materials (such as seeds) prior to sowing and/or are used in foliar or furrow applications.
[0003] A seed treatment is any material applied to a seed. Examples of seed treatments include, inter alia, pesticides, non-pesticide formularies, and mixtures thereof. Non-pesticide formularies generally include material such as surfactants, humectants, fillers, and polymers that influence the treated seed characteristics. Seed treatments are generally used on a variety of crops to control a variety of pests. Seed treatments are commonly used to ensure uniform stand establishment by protecting against soilborne diseases and insects. Systemic seed treatments may provide an alternative to traditional broadcast sprays of foliar fungicides or insecticides for certain early season airborne diseases and insects.
[0004] Pesticide seed treatments come in a variety of formulations: dry flowables (DF), liquid flowables (LF), true liquids (TL), emulsifiable concentrates (EC), dusts (D), wettable powders (WP), suspoemulsions (SE), water-dispersible granules (WG) and others. Some are registered for use only by commercial applicators using closed application systems, others are readily available for on-farm use as dusts, slurries, water soluble bags, or liquid ready-to-apply formulations.
[0005] Commercial seed treatment often requires specialized equipment to properly apply treatments or to treat large volumes of seed. For example, obtaining thorough seed coverage can be difficult when attempting to treat seed. For example, dry formulations can present unacceptable worker exposure to the fungicidal or insecticidal active ingredient. Problems can arise such as unacceptable drying times, material build-up in the seed treater, low seed flowability, poor seed coverage and dust-off of the pesticide from the seed prior to planting. As a result, handling is rendered difficult and the biological efficacy of the seed treatment may be reduced.
[0006] Seed coating additives are seed treatments used to remedy problems such as low seed flowability and excessive dust-off. However, it is well known that selection of a seed coating additive to reduce dust-off will likely have the adverse effect of decreasing seed flowability. Likewise, it is well known that selection of a seed coating to increase seed flowability will likely have the adverse effect of increasing dust-off.
SUMMARY [0007] The present technology provides for seed treatment compositions having improved adherence to plant propagation material with low dust-off. The compositions of the present technology have particular application in the protection of plant propagation materials, such as seeds, against pests when combined with one or more pesticides. [0008] The present technology thus provides an improved seed treatment suitable for applying to plant propagation materials. The seed treatments of the present technology include propylene glycol and talc. Such additions drastically improve the drying time of the seed treatment compositions, thereby improving the adherence to the seed. BRIEF DESCRIPTION OF THE DRAWINGS
[0009] FIG. 1 is a chart providing the results of Example 2. DETAILED DESCRIPTION
[0010] Propylene glycol, also called propane- 1,2-diol, has the chemical formula C3H8O2. As mentioned above, the use of propylene glycol in the compositions of the present invention aid in the drying times of the composition after it has been used to treat seeds. Although propylene glycol is sometimes utilized in seed treatment formulations, it is done so for its properties as an antifreeze component and not as a component for reducing drying times. In some embodiments, the amount of propylene glycol in the composition may be between about 2% and about 8% by weight of the composition. In additional embodiments, the amount of propylene glycol in the composition may be between about 4% and about 6% by weight of the composition. Still, in further embodiments, the amount of propylene glycol in the composition may be about 5% by weight of the composition.
[0011] In combination with the propylene glycol of the present invention, talc is utilized to aid in the drying times of the compositions of the present invention. However, certain amounts of talc may be necessary to ensure that the compositions of the present invention do not result in too much dust-off, forcing the composition off of the seed after treating. Accordingly, talc is utilized in the composition in an amount less than or equal to about 10% by weight of the composition. In further embodiments, talc is utilized in the composition in an amount less than or equal to about 9% by weight of the composition, or an amount less than or equal to about
8% by weight of the composition, or an amount less than or equal to about 7% by weight of the composition, or an amount less than or equal to about 6% by weight of the composition, or an amount less than or equal to about 5% by weight of the composition. Talc suitable for the present invention may include SILVERLINE 002 (magnesium silicate) (Fitz Chem of Itasca, IL) and SILVERLINE 202 (magnesium silicate) (Imerys Corporation of Sylacauga, AL). For example, in some embodiments, the talc may include magnesium silicate.
[0012] The propylene glycol and talc utilized in the compsositions of the present invention may also be expressed in the form of a ratio. For example, the ratio of propylene glycol to talc may be from about 2: l to about 1 :2, from about 1.5:1 to about 1 : 1.5, from about 1.2: 1 to about 1 :1.2 all by weight of the composition. Still, in further embodiments, the propylene glycol to talc may be about 1 :1 ratio by weight of the composition.
[0013] In some embodiments, the compositions of the present invention may reduce drying times of the compositions once applied to seeds to less than 5 hours. In additional
embodiments, the compositions of the present invention may reduce drying times of the composition once applied to seeds to less than 2 hours.
[0014] Seed treatment formulations applied to seeds generally comprise a pesticide, surfactants, film- forming polymers, carriers, antifreeze agents, and other formulary additives and when used together provide compositions that are storage stable and are suitable for use in normal seed treatment equipment, such as a slurry seed treater, direct treater, panogen treater or a mist-o-matic treater as well as on-farm hopper-box or planter-box treatments. Propagation materials treated with the compositions dry quickly, have good flowability, suitable coverage and have little or no dust-off. The compositions are advantageously combined with a pesticidally effective amount of at least one pesticide.
[0015] Pesticides [0016] The term "pesticide" as utilized herein is intended to cover compounds active against pests which are intended to repel, kill, or control any species designated a pest including weeds, insects, rodents, fungi, bacteria, or other organisms.
[0017] Examples of individual compounds of the above mentioned compound classes are listed below. Where known, the common name is used to designate the individual compounds (q.v. the Pesticide Manual, 12th edition, 2001, British Crop Protection Council).
[0018] Examples of pesticides include those selected from, for example and not for limitation, insecticides, acaricides, bactericides, fungicides, nematicides and molluscicides.
[0019] Suitable additions of insecticidally, acaricidally, nematicidally, or molluscicidally active ingredients are, for example and not for limitation, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenols and derivatives, formamidines, triazine derivatives, nitroenamine derivatives, nitro- and cyanoguanidine derivatives, ureas, benzoylureas, carbamates, pyrethroids, chlorinated hydrocarbons and Bacillus thuringiensis products. For example in some embodiments, the insecticides may include thiamethoxam, abamectin, cyanoimine, acetamiprid, thiodicarb, nitromethylene, nitenpyram, clothianidin, dinotefuran, fipronil, lufenuron, pyripfoxyfen, thiacloprid, fluxofenime; imidacloprid, Chloranthraniliprole, beta cyfiuthrin, lambda cyhalothrin, fenoxycarb, diafenthiuron, pymetrozine, diazinon, disulphoton; profenofos, furathiocarb, cyromazin, cypermethrin, tau-fiuvalinate, spinetoram, spinosad, sulfloxaflor, tefiuthrin or Bacillus thuringiensis products. In further embodiments, the pesticides of the present invention include thiamethoxam, mefenoxam and fludioxonil.
[0020] Suitable additions of fungicidally active ingredients are, for example and not for limitation, representatives of the following classes of active ingredients: strobilurins, triazoles, ortho-cyclopropyl-carboxanilide derivatives, phenylpyrroles, and systemic fungicides.
Examples of suitable additions of fungicidally active ingredients include, but are not limited to, the following compounds: azoxystrobin; bitertanol; carboxin; Cu20; cymoxanil;
cyproconazole; cyprodinil; dichlofluamid; difenoconazole; diniconazole; epoxiconazole;
fenpiclonil; fludioxonil; fiuoxastrobin, fluquiconazole; fiusilazole; flutriafol; furalaxyl;
guazatin; hexaconazole; hymexazol; imazalil; imibenconazole; ipconazole; kresoxim-methyl; mancozeb; metalaxyl; mefenoxam; metconazole; myclobutanil, oxadixyl, pefurazoate;
penconazole; pencycuron; prochloraz; propiconazole; pyroquilone; (±)-cz's-l-(4-chlorophenyl)-
2-(lH-l ,2,4-triazol-l -yl)cycloheptanol; sedaxane; spiroxamin; tebuconazole; thiabendazole; tolifluamide; triazoxide; triadimefon; triadimenol; trifioxystrobin, triflumizole; triticonazole and uniconazole.
[0021] In some embodiments, the pesticides of the present composition may include thiamethoxam, mefenoxam and fludioxonil.
[0022] In some embodiments, the pesticidally active compound or compound mixture is present in the composition in an amount of from about 0.05 % to about 50 % by weight, more specifically, from 2 to about 30% by weight of the entire composition. In further
embodiments, the pesticidally active compounds include between about 20 and 30% by weight of the composition.
[0023] Seed treatment application rates with respect to pesticidally active ingredients (compounds) may be between about 0.5 to 1000 g of pesticidally active compound per 100 kg seed. In further embodiments, application rate ranges with respect to seed treatments include: 0.5 to 500 g of pesticidally active compound per 100 kg seed; 0.5 to 250 g of pesticidally active compound per 100 kg seed; 0.5 to 100 g of pesticidally active compound per 100 kg seed; 0.5 to 75 g of pesticidally active compound per 100 kg seed; and 0.5 to 55 g of pesticidally active compound per 100 kg seed.
[0024] Surface Active Agent
[0025] Seed treatment compositions may also contain at least about 2% up to about 15% by weight of a surface-active agent. Compositions may contain from 3% up to 7% by weight of a surface -active agent. [0026] Generally the surface-active agent may comprise at least one nonionic surfactant and may optionally further comprise one or more anionic surfactants.
[0027] Exemplary nonionic surfactants include polyarylphenol polyethoxy ethers, polyalkylphenol polyethoxy ethers, polyglycol ether derivatives of saturated fatty acids, polyglycol ether derivatives of unsaturated fatty acids, polyglycol ether derivatives of aliphatic alcohols, polyglycol ether derivatives of cycloaliphatic alcohols, fatty acid esters of polyoxy ethylene sorbitan, alkoxylated vegetable oils, alkoxylated acetylenic diols, polyalkoxylated alkylphenols, fatty acid alkoxylates, sorbitan alkoxylates, sorbitol esters, C8- C22 alkyl or alkenyl polyglycosides, polyalkoxy styrylaryl ethers, alkylamine oxides, block copolymer ethers, polyalkoxylated fatty glyceride, polyalkylene glycol ethers, linear aliphatic or aromatic polyesters, organo silicones, polyaryl phenols, sorbitol ester alkoxylates, and mono- and diesters of ethylene glycol and mixtures thereof.
[0028] Specific examples of nonionic sufactants include: Genapol X-060 (Clariant) (ethoxylated fatty alcohol); Sorpohor BSU (Rhodia) (ethoxylated tristyrylphenol); Makon TD- 6 (Stepan) (ethoxylated fatty alcohol); BRIJ 30 (Uniqema) (ethoxylated lauryl alcohol);
Witconol CO-360 (Witco) (ethoxylated castor oil) Toximul 8320 (Stepan) (polyethylene- polypropylene glycol monobutyl ether); and Witconol NP-60 (Witco) (ethoxylated
nonylphenol). Suitable nonionic surfactants can be prepared by methods known per se and also are commercially available.
[0029] In general, the anionic surfactant may be any known in the art. Anionic surfactants are in general oligomers and polymers, as well as polycondensates, which contain a sufficient number of anionic groups to ensure their water-solubility. Anionic surfactants also include alcohol sulfates, alcohol ether sulfates, alkylaryl ether sulfates, alkylaryl sulfonates such as alkylbenzene sulfonates and alkylnaphthalene sulfonates and salts thereof, alkyl sulfonates, mono- or di-phosphate esters of polyalkoxylated alkyl alcohols or alkylphenols , mono- or di- sulfosuccinate esters of C12-C15 alkanols or polyalkoxylated C12-C15 alkanols, alcohol ether carboxylates, phenolic ether carboxylates, polybasic acid esters of ethoxylated polyoxyalkylene glycols consisting of oxybutylene or the residue of tetrahydrofuran, sulfoalkylamides and salts thereof such as N-methyl~N-oleoyltaurate Na salt, polyoxyalkylene alkylphenol carboxylates, polyoxyalkylene alcohol carboxylates alkyl polyglycoside/alkenyl succinic anhydride condensation products, alkyl ester sulfates, napthalene sulfonates, naphthalene formaldehyde condensates, alkyl sulfonamides, sulfonated aliphatic polyesters, sulfate esters of styrylphenyl alkoxylates, and sulfonate esters of styrylphenyl alkoxylates and their corresponding sodium, potassium, calcium, magnesium, zinc, ammonium, alkylammonium, diethanolammonium, or triethanolammonium salts, salts of ligninsulfonic acid such as the sodium, potassium, magnesium, calcium or ammonium salt, polyarylphenol polyalkoxyether sulfates and polyarylphenol polyalkoxyether phosphates, and sulfated alkyl phenol ethoxylates and phosphated alkyl phenol ethoxylates.
[0030] Specific examples of anionic surfactants include: Geropon T77 (Rhodia) (N- methyl--N-oleoyltaurate Na salt); Soprophor 4D384 (Rhodia) (tristyrylphenol sulphate); Reax 825 (Westvaco) (ethoxylated lignin sulfonate); Stepfac 8171 (Stepan) (ethoxylated
nonylphenol phosphate ester); Stepfac 8181 (Stepan) (tridecyl alcohol ethoxy late phosphate ester), Ninate 401-A (Stepan) (calcium alkylbenzene sulfonate); Emphos CS-131 (Witco) (ethoxylated nonylphenol phosphate ester); Ultrazine NA (sodium lignosulfonate); Ufoxane 3A, NA (sodium lignosulphonate); Morwet D-425 (sodium alkylnapthalenesulfonate), Reax 1425E (lignin sulfonate ethoxylate), and Atphos 3226 (Uniqema) (ethoxylated tridecylalcohol phosphate ester). Suitable anionic surfactants can be prepared by methods known per se and also are commercially available.
[0031] In addition to anionic and nonionic surfactants, certain cationic or zwitterionic surfactants also are suitable for use in the present invention such as alkanol amides of Cs-Cis fatty acids and Cs-Cis fatty amine polyalkoxylates, Cio-Cis alkyldimethylbenzylammonium chlorides, coconut alkyldimethylaminoacetic acids, and phosphate esters of Cs-is fatty amine polyalkoxylates.
[0032] Mixtures of non-ionic and anionic surfactants and optionally cationic or
zwitterionic surfactants may be employed as follows: (1) 0.5 - 4% by weight of a wetting agent selected from at least one anionic surfactant. Anionic surfactant wetting agents include sulfoalkylamides and salts thereof such as N-methyl~N-oleoyltaurate Na salt, alkylaryl sulfonates such as alkylbenzene sulfonates and alkylnaphthalene sulfonates and salts thereof and salts of ligninsulfonic acid; (2) 1 - 4% by weight of a dispersing agent selected from at least one anionic surfactant. Anionic surfactant dispersing agents include sulfate esters of styrylphenyl alkoxylates, and sulfonate esters of styrylphenyl alkoxylates and their
corresponding sodium, potassium, calcium, magnesium, zinc, ammonium, alkylammonium, diethanolammonium, or triethanolammonium salts; (3) 1 to 5% by weight of an emulsifying agent selected from at least one anionic surfactant, at least one nonionic surfactant and a mixture thereof. Suitable anionic/nonionic surfactant emulsifiers include salts of ethoxylated alkylphenols, polyoxyethylene-polyoxypropylene alkylphenols, (fatty) alcohol ethoxylates and ethoxylated tristyrylphenols. [0033] In some embodiments of the invention, the compositions may contain between about 1.5 and about 8 % by weight of surface active agents. In such embodiments, the compositions of the present invention may include about 1 to about 3 % by weight of an anionic surfactant and from about 0.5 to about 3 % by weight of a nonionic surfactant. Further, in such embodiments, the anionic surfactant may be tridecyl alcohol ethoxylate phosphate ester and the nonionic surfactant may be polyethylene -polypropylene glycol monobutyl ether. Even further, in such embodiments, the compositions of the present invention may include about 1% by weight of the nonionic surfactant and may also include about 2% by weight of an anionic surfactant.
[0034] In some embodiments, the composition may include the Morwet D-425 (sodium alkylnapthalenesulfonate) at about 0.2% by weight of the composition, Ultrazine NA (sodium lignosulfonate) at about 2.0% by weight of the composition, Stepfac 8181 (tridecyl alcohol ethoxylate phosphate ester) at about 2.0% by weight of the composition, Toximul 8320 (polyethylene -polypropylene glycol monobutyl ether) at about 1 .0% by weight of the composition, propylene glycol at about 5.0% by weight of the composition, and Silverline 002 (magnesium silicate) at about 5.0% by weight of the composition or at about 10.0% by weight of the composition.
[0035] Humectant
[0036] Seed treatment compositions may also include a humectant. A humectant is hygroscopic substance used to retain water. The compositions generally contain from 1% to 30 % by weight of the composition. By way of example, and not by limitation, commonly used formulation humectants include antifreezes, for example ethylene glycol, propylene glycol and glycerin. In examples where propylene glycol is utilized as a humectant the amount expressed above is in addition to the other amounts provided. [0037] Film-forming Polymer [0038] Seed treatment composition may also include at least one polymer selected from water-soluble and water-dispersible film-forming polymers. Suitable polymers generally have an average molecular weight of at least about 1 ,000 up to about 100,000; more specifically at least about 5,000, up to about 100,000. The compositions generally contain from about 0.5% to about 10% by weight of the composition of polymer. In a specific embodiment, the compositions contain from about 1.0% up to about 5% by weight of a film- forming polymer.
[0039] Polymers are generally selected from alkyleneoxide random and block copolymers such as ethylene oxide -propylene oxide block copolymers (EO/PO block copolymers) including both EO-PO-EO and PO-EO-PO block copolymers, ethylene oxide -butylene oxide random and block copolymers, C2-6 alkyl adducts of ethylene oxide -propylene oxide random and block copolymers, C2-6 alkyl adducts of ethylene oxide -butylene oxide random and block copolymers. Prospective polymers further include polyoxyethylene-polyoxypropylene monoalkylethers such as methyl ether, ethyl ether, propyl ether, butyl ether or mixtures thereof; vinylacetate/vinylpyrrolidone copolymers; alkylated vinylpyrrolidone copolymers;
polyvinylpyrrolidone; and polyalkyleneglycol including the polypropylene glycols and polyethylene glycols.
[0040] Specific examples of polymers include Pluronic PI 03 (BASF) (EO-PO-EO block copolymer), Pluronic P65 (BASF) (EO-PO-EO block copolymer), Pluronic PI 08 (BASF) (EO- PO-EO block copolymer), Vinamul 18160 (National Starch) (polyvinylacetate), Agrimer 30 (ISP) (polyvinylpyrrolidone), Agrimer VA7w (ISP) (vinyl acetate/vinylpyrrolidone
copolymer), Agrimer AL 10 (ISP) (alkylated vinylpyrrolidone copolymer), PEG 400
(Uniqema) (polyethylene glycol), Pluronic R 25R2 (BASF) (PO-EO-PO block copolymer), Pluronic R 31R1 (BASF) (PO-EO-PO block copolymer) and Witconol NS 500LQ (Witco) (butanol PO-EO copolymer).
[0041] In some embodiments of the invention, the compositions and methods lack a film- forming polymer that are provided above. As illustrated in the Examples provided below, the absence of such a film-forming polymer may aid in plantability of the composition. [0042] Antifreeze
[0043] The composition may also comprise an antifreeze from about 2 and up to about 30% by weight.
[0044] Specific examples of antifreezes include ethylene glycol, 1,2 -propylene glycol, 1,3- propylene glycol, 1,2-butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 1 ,4-pentanediol, 3-methyl- 1,5-pentanediol, 2,3-dimethyl-2,3-butanediol, trimethylol propane, mannitol, sorbitol, glycerol, pentaerythritol, 1,4-cyclohexanedimethanol, xylenol, bisphenols such as bisphenol A or the like. In addition, ether alcohols such as diethylene glycol, triethylene glycol, tetraethylene glycol, polyoxyethylene or polyoxypropylene glycols of molecular weight up to about 4000, diethylene glycol monomethylether, diethylene glycol monoethylether, triethylene glycol monomethylether, butoxyethanol, butylene glycol monobutylether, dipentaerythritol, tripentaerythritol, tetrapentaerythritol, diglycerol, triglycerol, tetraglycerol, pentaglycerol, hexaglycerol, heptaglycerol, octaglycerol and the like.
[0045] As a particular subset of suitable antifreeze materials there can be mentioned ethylene glycol, propylene glycol and glycerin. In examples where propylene glycol is utilized as an antifreeze, the amount expressed above is in addition to the other amounts provided.
[0046] Additional Components
[0047] The composition may also contain (e) at least one thickener. [0048] In one embodiment, the thickener is present in the aqueous composition in an amount from about 0.01% to about 25% by weight, more specifically from 0.02 to 10% by weight of the entire composition.
[0049] Illustrative of thickeners (water-soluble polymers which exhibit pseudoplastic properties in an aqueous medium) are gum arabic, gum karaya, gum tragacanth, guar gum, locust bean gum, xanthan gum, carrageenan, alginate salt, casein, dextran, pectin, agar, 2- hydroxyethyl starch, 2-aminoethyl starch, 2 -hydroxy ethyl cellulose, methyl cellulose, carboxymethyl cellulose salt, cellulose sulfate salt, polyacrylamide, alkali metal salts of the maleic anhydride copolymers, alkali metal salts of poly(meth)acrylate, and the like.
[0050] As suitable thickeners there may also be mentioned attapulgite-type clay, carrageenan, croscarmellose sodium, furcelleran, glycerol, hydroxypropyl methylcellulose, polystyrene, vinylpyrrolidone/styrene block copolymer, hydroxypropyl cellulose,
hydroxypropyl guar gum, and sodium carboxymethylcellulose.
[0051] The composition according to the invention can be employed together with the adjuvants customary in formulation technology, biocides, biostats, emulsifiers (lethicin, sorbitan, and the like), antifoam agents or application-promoting adjuvants customarily employed in the art of formulation. In addition, there may be mentioned inoculants and brighteners.
[0052] Additionally, a coloring agent, such as a dye or pigment (and the like such as described in the CFR 180.1001) is included in the seed coating so that an observer can immediately determine that the seeds are treated. The dye is also useful to indicate to the user the degree of uniformity of the coating applied.
[0053] The inventive compositions contain and/or may be applied together or sequentially with further active compounds. These further compounds can be fertilizers or micronutrient donors or other preparations that influence plant growth. They can also be selective herbicides, insecticides, fungicides, bactericides, insect growth regulators, plant growth regulators, nematicides, molluscicides or mixtures of several of these preparations.
[0054] Process
[0055] The pesticidal compositions of the invention can be prepared by processes known in the art.
[0056] In one embodiment, the compositions of the invention can be prepared by a process which comprises the steps: (a) forming a premix with at least one pesticidal compound, at least one surfactant, and water (b) forming a premix of a thickener and water, and (c) sequentially adding the premixes (a) and (b), talc, propylene glycol, the remaining ingredients, and water while stirring to form a homogeneous composition.
[0057] In another embodiment, the compositions of the invention can be prepared by combining commercially available seed treatment formulations with talc and propylene glycol.
[0058] Compositions
[0059] Pesticidal compositions in accordance with the invention may take the form of aqueous solutions, dispersions, suspensions, emulsions or suspoemulsions. In one
embodiment, the composition is a ready for use suspension or suspoemulsion.
[0060] Use [0061] The terms plant propagation material and seed, as defined herein, encompass both true seeds and other types of plant propagation material from which plants grow. Plant propagation material itself is commonly referred to as a seed and is defined as such herein. Many seed treatments are applied to true seeds, which have a seed coat surrounding an embryo. Seed treatments are also applied to plant propagation materials such as rhizomes, bulbs, corms or tubers.
[0062] In general, the amount of fungicide, insecticide or other ingredients used in the seed treatment are employed in amounts that do not inhibit generation of the seed or cause phytotoxic damage to the seed. The total amount of active ingredients is generally in the range of from about 0.05 % to about 50 % by weight, more specifically, from 15 to about 28% by weight of the entire composition. [0063] Suitable target seeds are especially those of corn, potatoes, cereals, (wheat, barley, rye, oats, rice), maize, sugar beet, cotton, millet varieties such as sorghum, sun flowers, beans, peas, oil plants such as canola, rape, soybeans, cabbages, tomatoes, eggplants (aubergines), pepper and other vegetables and spices as well as ornamental shrubs and flowers. Suitable target seeds also include those of transgenic crop plants of the foregoing varieties.
[0064] Suitable application rates of talc and propylene glycol to plant seeds is between 0.05 to 10.0 g/500g seed; 0.1 to 5.0 g/500g seed; 0.1 to 2.5 g/500g seed; 0.1 to 1.0 g/500g seed; and also between 0.25 to 1.0 g/500 g seed.
[0065] The techniques of seed treatment application are well known to those skilled in the art, and they may be used readily in the context of the present invention. The compositions of the invention are applied to the seed as slurry or a soak. There also may be mentioned, e.g., film coating or encapsulation. The coating processes are well known in the art, and employ, for seeds, the techniques of film coating or encapsulation, or for the other multiplication products, the techniques of immersion. The method of application of the inventive compositions to the seed may be varied and the technology is intended to include any technique that is to be used. [0066] As noted above, the compositions of the present technology may be formulated or mixed in the seed treater tank or combined on the seed by overcoating with other seed treating agents. The agents to be mixed with the compounds of this invention may be for the control of pests, nutrition, and the control of plant diseases. [0067] A feature of the technology is that it provides for a treated seed with a reduction in drying times over conventional seed treatments while at the same time reducing excess dust. Accordingly, the formulation aids in reducing the associated health hazards to those who work with treated seeds, such as processing plant employees, truck drivers, warehouse workers, and farmers.
[0068] Still another feature of the technology is the uniform coating of-seeds with non- dusting seed treatment which will not interfere with germination and sprouting of the seed but which will protect the seed against seed-borne pathogens.
[0069] EXAMPLES
[0070] In order that those skilled in the art will be better able to practice the technology, the following examples are given by way of illustration and not by way of limitation. In the following examples, as well as elsewhere in the specification and claims, temperatures are in degrees Celsius, the pressure is atmospheric and all parts are by weight, unless otherwise clearly indicated.
[0071] Example 1 -Testing of formulation concepts
[0072] Three different formulation were tested to determine effectiveness of the inventive concept provided above. Each formulation included thiamethoxam (22.62 % by weight), fludioxonil (1.12 % by weight), and mefenoxam (1.70 % by weight). Formulation B also included propylene glycol (5.0 % by weight) and Formulation C included propylene glycol (5.0 % by weight) and talc (Silverline 002 5.0 % by weight). [0073] Coating Evaluation - On Film - Each of the formulations prior to being applied to seeds were placed on a plastic film and allowed to dry. The drying times of each formulation are provided in the Table below.
[0074] Table 1
Drying time
Formulation A Very wet for 3 days, remained tack to
the touch after 1 month
Formulation B Dry to the touch within 1 day Formulation C Dry to the touch within 2 hours
[0075] Soybean seeds were then treated with each of the three different formulations (A, B, and C) to measure wet flow (g/sec), and dry flow (g/sec).
[0076] Wet flow Measurement - Seeds are taken immediately from the treater and are weighed. The seeds are then placed in a Cox funnel having a 1 .25 inch opening at the stem. The funnel door is opened and a stopwatch concurrently started. The funnel may be tapped lightly if seeds begin to clump. The stopwatch is stopped when the last seed flows from the funnel. The seeds are poured back into the funnel two times and the above procedure repeated for a total of three measurements. The flow measurements are then calculated and averaged.
[0077] Dry flow Measurement - Seeds are taken from the treater and allowed to dry completely (approximately 24 hours) and are then weighed. The seeds are then placed in a Cox funnel having a 1.25 inch opening at the stem. The funnel door is opened and a stopwatch concurrently started. The funnel may be tapped lightly if seeds begin to clump. The stopwatch is stopped when the last seed flows from the funnel. The seeds are poured back into the funnel two times and the above procedure repeated for a total of three measurements. The flow measurements are then calculated and averaged.
[0078] Table 2
Wet flow (g/sec) Dry flow (g/sec)
Formulation A 1 1.52 7.38
Formulation B 10.22 7.36
Formulation C 9.22 6.89 [0079] As shown in Tables 1 and 2, the combination of talc and propylene glycol provide advantages in drying times and in fiowability of the seed. [0080] Example 2A - Formulation Comparisons
[0081] Five different compositions (A, B, C, D and E shown in Table 3) were prepared and treated onto soybean seeds, and tested under various conditions to determine the plantability of the seed against untreated soybean seeds. The four different compositions were treated on soybean seeds of the variety Waseguro. Once the seeds were treated with the appropriate composition, they were immediately placed in a plastic container. The seeds were then stored at various temperatures and different relative humidity (RH) and were allowed to dry at different intervals. The drying times and conditions are provided: (1) seeds stored at 25 °C with RH of 60-70% for 30 mins; (2) seeds stored at 25°C with RH of 60-70% for 3 hours; (3) seeds stored at 25°C with RH of 60-70% for 24 hours; (4) seeds stored at 40°C with RH of 98% for 1 hour; and (5) seeds stored at 40°C with RH of 98% for 4 hours. Once the allotted time was completed, the seeds were placed in a roll-type seeder, which was run for two minutes and the discharged seeds were collected. The weight of the discharged seeds were recorded and each test was repeated three times. Each test was repeated three times (any seeds trapped in the holes were removed after each test). The machine was cleaned after evaluation of each sample and verified to be clean by running the test with untreated seeds in between samples. Cruiser FS30 was included as a standard, because this is known to have good plantability
characteristics.
[0082] Table 3
Figure imgf000018_0001
Morwet D-425 0.20 0.20 0.20 0.20 0.20
Ultrazine NA 2.00 2.00 2.00 2.00 2.00
Stepfac 8181 2.00 2.00 2.00 2.00 2.00
Toximul 8320 1.00 1.00 1.00 1.00 1.00
Propylene 5.00 5.00 5.00 5.00 5.00 Glycol
Vinamul 18462 ~ ~ ~ 2.00 2.00
Silverline 002 5.00 10.00 5.00 5.00 10.00
Additional 59.36 54.36 59.36 57.36 52.36 Components
[0083] The only difference between formulations A and C is the specific acticide used.
[0084] The findings of the falling seed weight vs. seed weight of untreated seeds (as a percentage) is provided in Table 4 and Figure 1.
[0085] Table 4
Figure imgf000019_0001
[0086] A falling seed weight less than 100% indicates impaired plantability compared with untreated seeds. The results show that formulations A to E of the present invention all give better plantability compared with the CruiserMaxx or Cruiser FS30 commercial standards, especially under high humidity conditions. Treatments without binder (formulations A,B,C) showed better plantability after 30 minutes drying in comparison with treatments containing the binder (formulations D and E); the presence of a film- forming polymer may inhibit flowability of seeds at certain temperatures and relative humidity. Such finding is of immense importance, as many seeds are planted under very hot and humid conditions.
[0087] Formulations A to E in Table 3 were further compared against a standard
CruiserMaxx seed treatment; CruiserMaxx does not contain propylene glycol or talc.
[0088] Example 2B - Peeling test
[0089] A test was conducted to evaluate peeling of the seed treatment off the treated seeds. lOOg of treated seeds were placed in a sealed plastic bottle, and the bottle placed into the oven at 60°C for 2hr. The bottle was set on a ball mill (dew drop is generated inside of the bottle from the seed moisture), and rotated for 5min at 28rpm at 25°C. The appearance was then assessed visually for peeling. Less peeling was observed for seeds treated with CruiserMaxx and either polymer or talc. The results show that both polymer and talc prevented peeling off of CruiserMaxx from the coated seeds.
[0090] Example 2C - Dust off and drying time
[0091] Drying time was assessed at regular time intervals after seed treatment, and dust-off was measured using industry standard methods. The results are presented in Table 5.
[0092] Table 5: Dust-off and drying time of treated seeds
Figure imgf000020_0001
CruiserMaxx (standard) 0.1 mg Remained wet/tacky after 2 weeks
Formulation A 0.4 mg Dry to the touch after 1 hour
Formulation B 0.5 mg Dry to the touch after 30 minutes
Formulation C 0.4 mg Dry to the touch after 1 hour
Formulation D 0.2 mg Dry to the touch after 1 hour
Formulation E 0.2 mg Dry to the touch after 30 minutes
[0093] Dust-off levels were similar for all formulations, and all within acceptable levels for seed treatment formulations. The addition of propylene glycol was found to dramatically speed up drying time compared with glycerine in the CruiserMaxx standard. Further, the addition of 5% talc dramatically accelerated drying time without causing dust-off issues. The addition of 10% talc did not further improve drying time. The presence or absence of a binder has little effect on drying time but does marginally improve dusting properties.
[0094] Example 2D - Dry flow
[0095] A funnel flow test was carried out to determine fiowability of treated soybean seeds after storage for 3 hours at 25°C and 75% relative humidity: a funnel was set on a stand with a poly beaker beneath. A plastic plate was set between the funnel and the poly beaker. 400g of coated seeds were placed in the funnel. The plastic plate was removed quickly, and the time until all seeds are fallen measured by stop watch (n=6).
[0096] Additionally, an FT4 instrument was used to measure the resistance of seeds to flow while the seeds are in motion. A precision 'blade', or impeller, is rotated and moved downwards and upwards through the sample to establish a precise flow pattern. This causes many particles/seeds to interact, or flow relative to one another, and the resistance experienced by the blade represents the difficulty of this relative particle movement, or the bulk flow properties. The more the particles resist motion and the harder it is to get the powder to flow, the more difficult it is to move the blade. This resistance is measured as the force required to move the seeds and presented as Down Energy or Up Energy. The less force, the better the flow properties of a treated seed. Resistance to flow can create issues with seed handling and plantability. Good flow properties related to the tackiness of the seeds not only immediately after treatment but after the drying process.
[0097] The results are presented in Table 6 as a mean of 6 replicates.
[0098] Table 6: Dry flow time of 400g treated soybean seed
Figure imgf000022_0001
[0099] Seeds treated with propylene glycol and talc (formulation A to E) exhibited faster dry flow times than the CruiserMaxx standard.

Claims

What is claimed is:
1. A composition comprising:
a pesticidally active ingredient in a concentration between about 20 and about 30% by weight of the composition;
propylene glycol in a concentration between about 1 and about 10% by weight of the composition; and
talc in a concentration less than about 10% by weight of the composition, and wherein the ratio of propylene glycol to talc is from about 1.5: 1 to about 1 : 1.5.
2. The composition of claim 1 , wherein the talc is less than about 7% by weight of the composition.
3. The composition of claim 1 , wherein the talc is about 5% by weight of the composition.
4. The composition of claim 1 , wherein the pesticidally active ingredients include
thiamethoxam, mefenoxam, and fiudioxonil.
5. The composition of claim 4, wherein:
thiamethoxam is in a concentration of between about 21 and about 24% by weight of the composition;
fiudioxonil is in a concentration of between about 0.5 and about 2% by weight of the composition; and
mefenoxam is in a concentration of between about 0.5 and 2.5% by weight of the composition.
6. The composition of claim 1 , wherein the propylene glycol is about 5% by weight of the composition.
7. The composition of claim 1, wherein the composition further comprises an anionic and a nonionic surfactant that in total are in a concentration between about 1.5 and about 8% by weight of the composition.
8. The composition of claim 7, wherein the anionic surfactant and the nonionic surfactant are each in a concentration from about 0.5 to about 3% by weight of the total concentration.
9. The composition of claim 7, wherein the anionic surfactant is tridecyl alcohol ethoxylate phosphate ester and wherein the anoionic surfactant is in a concentration of about 2% by weight of the composition.
10. The composition of claim 7, wherein the nonionic surfactant is polyethylene- polypropylene glycol monobutyl ether and wherein the nonionic surfactant is in a concentration of about 1% by weight of the composition.
1 1. The composition of claim 1 , wherein the composition does not include a film- forming polymer.
12. A method of reducing the time for a seed treatment composition to dry after applying to a seed comprising:
treating a seed with the composition of claim 1 , wherein the seed is dry to the touch within 5 hours of treating the seed.
13. The method of claim 12, wherein the seed is dry to the touch within 2 hours of treating the seed.
PCT/EP2018/060030 2017-05-12 2018-04-19 Pesticide compositions Ceased WO2018206253A1 (en)

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