WO2015130893A1 - Oligoglucosamines synthétiques pour l'amélioration de la croissance et du rendement de végétaux - Google Patents

Oligoglucosamines synthétiques pour l'amélioration de la croissance et du rendement de végétaux Download PDF

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Publication number
WO2015130893A1
WO2015130893A1 PCT/US2015/017666 US2015017666W WO2015130893A1 WO 2015130893 A1 WO2015130893 A1 WO 2015130893A1 US 2015017666 W US2015017666 W US 2015017666W WO 2015130893 A1 WO2015130893 A1 WO 2015130893A1
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agricultural composition
product
seed
substantially pure
plant
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PCT/US2015/017666
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English (en)
Inventor
Shane Francis KENDRA
Subramaniam Sabesan
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E. I. Du Pont De Nemours And Company
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical

Definitions

  • the present disclosure relates to formulations and methods of use of synthetic oligoglucosamines for improving plant growth and crop yield.
  • the present disclosure provides compositions and methods for improving plant growth and crop yield. More specifically, the present disclosure relates to agricultural compositions comprising synthetic oligoglucosamines of Structure A. These agricultural compositions may be applied to propagating materials, including seeds and other materials.
  • regenerate plant parts including cuttings, bulbs, rhizomes and tubers. They may also be applied to foliage, or soil either prior to or following planting of propagating materials. Such applications may be made alone or in combination with fungicides, insecticides, nematicides and other agricultural agents used to improve plant growth and crop yield.
  • compositions comprising a substantiall pure compound represented by Structure A;
  • n 0, 1 or 2;
  • XR 1 is an azide group or X is O or S and R 1 is hydrogen, a linear or branched, saturated or unsaturated hydrocarbon containing from 1 to 20 carbon atoms, aryl, or substituted aryl; each R 2 and R 3 are independently hydrogen, an alkyl group having in the range of from 1 to 20 carbon atoms.
  • the agricultural composition comprises Product 13 and/or Product 14;
  • any one or more of the agricultural compositions may be used, wherein the above substantially pure compounds of Structure A are present at a concentration in the range of from 10 "3 moles/liter (M) to 10 "12 M, or present in the composition at a concentration of about 10 "7 M.
  • the substantially pure compounds of Structure A are present in the agricultural composition in the range of from 10 "3 M to 10 "4 M.
  • the substantially pure compounds of Structure A are present in the agricultural composition in the range of from 10 "4 M to 10 "5 M.
  • the substantially pure compounds of Structure A are present in the agricultural composition in the range of from 10 "5 M to 10 "6 M.
  • the substantially pure compounds of Structure A are present in the agricultural composition in the range of from 10 "6 M to 10 "7 M.
  • the substantially pure compounds of Structure A are present in the agricultural composition in the range of from 10 "7 M to 10 "8 M.
  • the substantially pure compounds of Structure A are present in the agricultural composition in the range of from 10 "8 M to 10 "9 M.
  • the substantially pure compounds of Structure A are present in the agricultural composition in the range of from 10 "9 M to 10 "10 M. In other embodiments, the substantially pure compounds of
  • Structure A are present in the agricultural composition in the range of from 10 "10 M to 10 "1 1 M.
  • Structure A are present in the agricultural composition in the range of from 10 "1 1 M to 10 "12 M.
  • the agricultural composition can further comprise one or more signal molecules.
  • the signal molecule can be a
  • the agricultural composition is applied to propagating material of a plant.
  • the propagating material is a seed.
  • the propagating material is corn or soybean or a seed potato.
  • the agricultural composition is applied to the seed as a seed coating to increase rate of germination, seedling
  • the agricultural composition is applied to foliage.
  • the agricultural composition is applied to soil either prior to or following planting plant propagating material.
  • the present disclosure relates to a method for treating a plant, propagating materials, foliage or soil, comprising applying the agricultural composition to the plant, propagating materials, foliage or soil.
  • the method utilizes an agricultural composition comprising one or both of Products 13 and/or 14.
  • any one or more of the foregoing compositions may be applied to a legume, such as soybean, or to a non- legume, such as corn.
  • agricultural composition as used herein comprises one or more substances formulated for at least one agricultural application.
  • Agricultural applications are understood to include, but not be limited to, yield improvement, pest control, disease control and resistance to abiotic environmental stress.
  • biologically effective amount refers to that amount of a substance required to produce the desired effect on a plant, plant propagating material and/or plant part, such as, for example, germination improvement, growth improvement, yield improvement, pest control, disease control and resistance to abiotic environmental stress. Effective amounts of the composition will depend on several factors, including treatment method, plant species, propagating material type and environmental conditions.
  • Foliage as defined in the present application includes all aerial plant organs, that is, the leaves, stems, flowers and fruit.
  • percent germination refers the percentage of seeds that germinate after planting or being placed under conditions otherwise suitable for germination.
  • accelerate the rate of germination and its equivalents refer to an increase in the percent germination of experimentally treated seeds compared to seeds
  • seed germination rates were determined with laboratory-based germination assays conducted under optimum conditions for germination wherein germination percentages were determined at a specified time following initiation of the experiment. General descriptions of seed germination tests can be found in the Handbook of Seed
  • Plant “growth” as used herein is defined by, but not limited to, measurements of seedling emergence, standability, radicle growth, early growth, plant height, time to flowering, tillering (for grasses), days to maturity, vigor, biomass and yield.
  • propagating material means a seed or regenerable plant part.
  • the term “regenerable plant part” means a part of the plant other than a seed from which a whole plant may be grown or regenerated when the plant part is placed in agricultural or horticultural growing media such as moistened soil, peat moss, sand, vermiculite, perlite, rock wool, fiberglass, coconut husk fiber, tree fern fiber, and the like, or even a completely liquid medium such as water.
  • Regenerable plant parts commonly include rhizomes, tubers (including seed potatoes), bulbs and corms of such geophytic plant species as potato, sweet potato, yam, onion, dahlia, tulip, narcissus, etc.
  • Regenerable plant parts include plant parts that are divided (e.g., cut) to preserve their ability to grow into a new plant. Therefore regenerable plant parts include viable divisions of rhizomes, tubers, bulbs and corms which retain meristematic tissue, such as an eye. Regenerable plant parts can also include other plant parts such as cut or separated stems and leaves from which some species of plants can be grown using horticultural or agricultural growing media.
  • seed includes both unsprouted seeds and seeds in which the testa (seed coat) still surrounds part of the emerging shoot and root.
  • rhizosphere refers to the area of soil that immediately surrounds and is affected by the plant's roots.
  • treating means applying a biologically effective amount of a substantially pure Structure A compound, or a composition containing a substantially pure Structure A compound, to a seed or other propagating material, foliage or plant rhizosphere; related terms such as “treatment” are defined analogously.
  • yield refers to the return of crop material per unit area obtained after harvesting a plant crop.
  • An increase in crop yield refers to an increase in crop yield relative to an untreated control treatment.
  • Crop materials include, but are not limited to, seeds, fruits, roots, tubers, leaves and types of crop biomass. Descriptions of field-plot techniques used to evaluate crop yield may be found in W.R. Fehr, Principles of Cultivar Development, McGraw-Hill, Inc., New York, NY, 1987, pp. 261 -286 and references incorporated therein.
  • Insect resistant trait is used herein to refer to a plant containing a toxin that has toxic acitivity against one or more pests, including, but not limited to, members of the Lepidoptera, Diptera, Hemiptera and
  • Pesticidal proteins have been purified from organisms including, for example, Bacillus sp., Pseudomonas sp., Photorhabdus sp., Xenorhabdus sp., Clostridium bifermentans and Paenibacillus popilliae. Pesticidal proteins include but are not limited to: insecticidal proteins from Pseudomonas sp. such as PSEEN3174 (Monalysin; (201 1 ) PLoS
  • the present disclosure provides an agricultural com osition comprising substantially pure compounds of Structure A;
  • Structure A is Product 13
  • the substantially pure compound of Structure A is roduct 14;
  • the agricultural composition comprises the substantially pure compound of Structure A at a concentration of about 10 "5 M to 10 "12 M.
  • the agricultural composition is applied to propagating material.
  • the propagating material is a seed of wheat, durum wheat, barley, oat, rye, maize (corn), sorghum, rice, wild rice, cotton, flax, sunflower, soybean, garden bean, lima bean, broad bean, garden pea, peanut, alfalfa, beet, garden lettuce, rapeseed, cole crop, turnip, leaf mustard, black mustard, tomato, potato, pepper, eggplant, tobacco, cucumber, muskmelon, watermelon, squash, carrot, zinnia, cosmos, chrysanthemum, sweet scabious, snapdragon, gerbera, babys- breath, statice, blazing star, lisianthus, yarrow, marigold, pansy, impatiens, petunia, geranium and coleus.
  • the agricultural composition is applied to seed to accelerate the rate of germination, seedling emergence, radicle growth, early growth, plant height, vigor, biomass and/or yield.
  • the agricultural composition further comprises one or more insecticides, fungicides, nematocides, bactericides, acaricides, entomopathogenic bacteria, viruses or fungi, plant growth regulators, rooting stimulant, chemosterilant, repellent, attractant, pheromone, feeding stimulant, apocarotenoid, flavonoid, jasmonate or strigolactone.
  • the agricultural composition can be applied to foliage.
  • the agricultural composition is applied to soil either prior to or following the planting of propagating material.
  • the present disclosure relates to a method for treating a plant, propagating materials, foliage or soil, comprising applying the agricultural composition to the plant, propagating materials, foliage or soil.
  • the agricultural composition comprises a substantially pure compound having a structure of Product 13;
  • the agricultural composition comprises a substantially pure compound having a structure of Product 14
  • the agricultural composition is applied as a seed coating.
  • the agricultural composition is applied to foliage.
  • the agricultural composition is applied to soil either prior to or following the planting of the propagating material.
  • the agricultural composition is applied to a dicot.
  • the agricultural composition is applied to soybean.
  • the agricultural composition is applied to a monocot.
  • the agricultural composition is applied to corn.
  • US Patent Number 7,485,7108 describes an efficient chain extension coupling of single glucosamine monomers, providing compounds having a defined chain length. This process allows the efficient construction of compounds of Structure A wherein n is a known whole number.
  • the substantially pure compounds of Structure A are synthetic compounds produced via a step-wise polymerization from a glucosamine monomer or a monomeric glucosamine derivative.
  • Structure A and “substantially pure Structure A compound” mean that the disclosed composition contains less than 10 percent by weight of compounds of Structure A wherein n is greater than or equal to 3, based on the total weight of the compounds of Structure A in the composition. In some embodiments, the disclosed composition contains less than 5 percent by weight of compounds of Structure A wherein n is greater than or equal to 3, and in other embodiments, contains less than 2 percent by weight of compounds of Structure A wherein n is greater than or equal to 3. It should be noted that the phrase "substantially pure” when used to describe compounds of Structure A refers only to those compounds represented by Structure A and having a value of n that is greater than or equal to 0. As one of ordinary skill in the art would know, other reaction impurities (i.e., compounds not having a structure represented by
  • Structure A) may be present and this phrase does not exclude the possibility of other reaction impurities being present in the disclosed compositions.
  • compound of Structure A can be applied as a seed treatment formulation, as a seed coating composition, as a foliar formulation, as a sprayable foliar formulation or as a formulation suitable for treating the growing medium.
  • Such formulations typically contain from about 10 "3 M to 10 "12 M of a substantially pure compound of Structure A. In other embodiments, formulations contain from about 10 "6 M to 10 "10 M of a substantially pure Structure A compound.
  • the locus of the propagating materials can be treated with a substantially pure Structure A compound by many different methods. All that is needed is for a biologically effective amount of a substantially pure Structure A compound to be applied on or sufficiently close to the propagating material so that it can be absorbed by the propagating material.
  • the substantially pure Structure A compound can be applied by such methods as drenching the growing medium including a propagating material with a solution or dispersion of a substantially pure Structure A compound, mixing a substantially pure Structure A compound with growing medium and planting a propagating material in the treated growing medium (e.g., nursery box treatments), or various forms of propagating material treatments whereby a substantially pure Structure A compound is applied to a propagating material before it is planted in a growing medium.
  • the agricultural can provide increased plant growth, an increased rate of germination, an increased rate of seedling emergence, an increased rate of radicle growth, an increased rate of early growth, increased pest control, increased disease control, increased plant height, increased vigor, increased resistance to abiotic environmental stress, and increased biomass and/or yield when compared to an untreated control.
  • the substantially pure compound of Structure A can be used as a seed treatment formulation with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant.
  • an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant.
  • liquids such as solutions (including emulsifiable concentrates),
  • Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible (“wettable”) or water-soluble.
  • wettable water-dispersible
  • Structure A can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation comprising the substantially pure compound of Structure A can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the substantially pure compound of Structure A.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare.
  • High-strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of the substantially pure compound of Structure A, diluent and surfactant within the following approximate ranges that add up to 100 percent by weight.
  • Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Emulsifiers and Detergents and McCutcheon's Functional Materials (North America and International Editions, 2001 ), The Manufacturing Confection Publ. Co., Glen Rock, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
  • Surfactants include, for example, ethoxylated alcohols, ethoxylated alkylphenols, ethoxylated sorbitan fatty acid esters, ethoxylated amines, ethoxylated fatty acids, esters and oils, dialkyl sulfosuccinates, alkyl sulfates, alkylaryl sulfonates, organosilicones, ⁇ /,/V-dialkyltaurates, glycol esters, phosphate esters, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and block polymers including polyoxyethylene/polyoxypropylene block copolymers.
  • Solid diluents can include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Liquid diluents can include, for example, water, or an organic diluent, for example, ⁇ /,/V-dimethylformamide, dimethyl sulfoxide, ethyl acetate, diethyl ether, formamide, 2-pyrrolidone, N-methylpyrrolidone, /V-alkylpyrrolidone, ethylene glycol, polypropylene glycol, 1 ,3-propane diol, 1 ,3-propane diol polyethers, alkyl and dialkyl ethers of 1 ,3-propane diol, alkyl and dialkyl ethers of 1 ,3-propane diol polyethers, diethylene glycol, diethylene glycol ethers, dipropylene glycol ethers, diglyme, hexamethylene glycol, pentamethylene glycol,
  • polyethylene glycol poly hydroxy I ated alkanes, propylene glycol ethers, tetramethylene glycol, tetramethylene glycol ethers, triethylene glycol, triethylene glycol ethers, tripropylene glycol, tripropylene glycol ethers, 1 ,3- butylene glycol, 1 ,3-butylene glycol ethers, butylene carbonate, glycerol, thiodiglycol, propylene carbonate, dibasic esters, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as, for example, acetone, gamma-butyrolactone, methyl ethyl ketone, cyclohexanone, 2-heptanone, isophorone and 4-hydroxy
  • tetrahydrofurfuryl alcohol polyethylene glycol ether, isopropanol, propanol, methanol, cyclohexanol, decanol, benzyl and tetrahydrofurfuryl alcohol, phosphoric acid esters, sulfolane, tetrahydrofuran or a combination thereof.
  • the agricultural composition can comprise in the range of 80 to 100 percent by weight of water, based on the total weight of the liquid diluent.
  • the liquid diluent can comprise in the range of from 90 to 100 percent water, and, in still further embodiments, in the range of from 95 to 100 percent water, wherein the percentages by weight are based on the total amount of the liquid diluent.
  • the remaining amount of liquid diluent can be one or more of the organic diluents listed above.
  • Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill.
  • Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084.
  • Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp. 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pp. 8-57 and following, and PCT
  • Pellets can be prepared as described in U.S. 4,172,714.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493.
  • Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030.
  • Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
  • biocides can include, for example, 5-chloro-2- methyl-3(2H)-isothiazolone , o-phenylphenol, sodium-o-phenylphenate, cis-1 -(chloroallyl)-3,5,7-triaza-1 -azoniaadamantane chloride, 7-ethyl bicyclooxazolidine, 2,2-dibromo-3-nitrilopropionamide, bronopol, glutaraldehyde, copper hydroxide, cresol, dichlorophen, dipyrithione, fenaminosulf, formaldehyde, hydrargaphen, 8-hydroxyquinoline sulfate, kasugamycin, nitrapyrin, octhilinone, oxolinic acid, oxytetracycline, probenazole, streptomycin, tecloftalam,
  • the agricultural compositions used for treating propagating materials, or plants grown therefrom, according to this disclosure can also comprise (besides the substantially pure Structure A compound) an effective amount of one or more other biologically active compounds or agents.
  • Suitable biologically active compounds or agents include, but are not limited to, insecticides, fungicides, nematocides, bactericides, acaricides, entomopathogenic bacteria, viruses or fungi, plant growth regulators such as rooting stimulants, chemosterilants, repellents, attractants, pheromones, feeding stimulants and other signal compounds including, but not limited to, apocarotenoids, flavonoids, jasmonates and strigolactones (Akiyama, et al., in Nature, 435:824-827 (2005); Harrison, in Ann.
  • Biologically active agents can also comprise
  • microorganisms that stimulate plant growth.
  • Such microorganisms include, but are not limited to, biologically active species within the bacterial genera Azorhizobium, Bacillus, Bradyrhizobium, Mesorhizobium, Paenibacillus and Rhizobium (Khan, et al., in Bioresource Technology, 99(8): 3016-3023 (2008); Plant Growth and Health Promoting Bacteria (Microbiology
  • microorganisms also include, but are not limited to, plant growth promoting species within the fungal genera Cladosporum, Corvularia, Fusarium, Gliocladium, Metarhizium, Penicilliunn and Trichoderma (Kim, et al. in BMC Microbiology, 8:231 (2008); Khan, et al., in World Journal of Microbiology and Biotechnology, 28(4): 1483-1494 (2012), Biotechnology of Microbes and Sustainable Utilization, R. C. Rajak, Ed., Scientific Publishers,
  • insecticides such as abamectin, acephate, acetamiprid, amidoflumet (S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos- methyl, chromafenozide, clothianidin, cyantraniliprole, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, em
  • methamidophos methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, noviflumuron (XDE-007), oxamyl, parathion, parath ion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, spiromesifin (BSN 2060), sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos,
  • fungicides such as acibenzolar, azoxystrobin, benomyl, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), bromuconazole, carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, (S)-3,5-dichloro-/V-(3- chloro-1 -ethyl-1 -methyl-2-oxopropyl)-4-methylbenzamide (RH 7281 ), diclocymet (S-2900), diclomezine,
  • metominostrobin/fenominostrobin SSF-126
  • metrafenone AC 375839
  • myclobutanil neo-asozin (ferric methanearsonate), nicobifen (BAS 510), orysastrobin, oxadixyl, oxathiapiprolin, penconazole, pencycuron, penflufen, penthiopyrad, picoxystrobin, probenazole, prochloraz, propamocarb, propiconazole, proquinazid, prothioconazole (JAU 6476), pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, sedaxane, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, t
  • nematocides such as aldicarb, oxamyl and fenamiphos
  • bactericides such as streptomycin
  • acaricides such as amitraz, chinomethionat
  • chlorobenzilate cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and biological agents including Bacillus thuringiensis (including ssp.
  • Bacillus amyloliquifaciens 22CP1 ATCC PTA-65008
  • Bacillus amyloliquifaciens 15AP4 ATCC PTA-6507
  • amyloliquifaciens 22CP1 was deposited at the American Type Culture Collection (ATCC), 10801 University Boulevard., Manassas, Virginia 201 10- 2209 and given accession number PTA-6508. The deposits were made under the provisions of the Budapest Treaty on the International
  • the agricultural composition can comprise the substantially pure compounds of Structure A and Bacillus
  • the agricultural composition can comprise at least one of the substantially pure
  • the anthranilamide insecticides which includes chlorantraniliprole and cyantraniliprole, comprises a large class of compounds having insecticidal activity.
  • the agricultural composition can further comprise and one of the compounds of Structure 1 , including N-oxides or salts therefrom;
  • X is N, CF, CCI, CBr or CI
  • R 7 is CH 3 , CI, Br or F
  • R 8 is H, F, CI, Br or -CN
  • R 9 is F, CI, Br, C1 to C4 haloalkyl, C1 to C4 haloalkoxy or Q;
  • R 11 is H, F, CI or Br
  • R 12 is H, F, CI or Br
  • each R 13 and R 14 is independently H, C1 to C6 alkyl, C3 to C6 cycloalkyl, cyclopropyl methyl or 1 -cyclopropylethyl;
  • Q is a -CH 2 -tetrazole radical.
  • Suitable embodiments for Q can include any structure having a formula according to Q-1 to Q-1 1 ;
  • the agricultural composition can further comprise any of the known anthranilic diamide insecticides, for example, those described in US 6,747,047, US 8,324,390, US 2010/0048640, WO 2007/006670, WO 2013/024009, WO 2013/024010,
  • the plant growth regulators for mixing with the substantially pure Structure A compounds used in compositions for treating stem cuttings are 1 H-indole-3-acetic acid, 1 H-indole-3-butanoic acid and 1 -naphthaleneacetic acid and their agriculturally suitable salt, ester and amide derivatives, such as 1 -napthaleneacetamide.
  • Preferred fungicides for mixing with the substantially pure Structure A compounds include fungicides useful as seed treatments such as thiram, maneb, mancozeb and captan.
  • microorganisms can be added to the agricultural composition.
  • Suitable examples of microorganisms can include, for example, a phosphate solubilizing microorganism.
  • phosphate solubilizing microorganism is a microorganism that is able to increase the amount of phosphorous available for a plant.
  • Phosphate solubilizing microorganisms include fungal and bacterial strains.
  • the phosphate solubilizing microorganism is a spore forming microorganism.
  • the phosphate solubilizing microorganisms can include, for example, species from a genus selected from the group consisting of Acinetobacter, Arthrobacter, Arthrobotrys, Aspergillus, Azospirillum, Bacillus, Burkholderia, Candida Chryseomonas,
  • Streptosporangium Swaminathania, Thiobacillus, Torulospora, Vibrio, Xanthobacter, and Xanthomonas.
  • the phosphate solubilizing microorganisms can include, for example, Acinetobacter calcoaceticus, Acinetobacter sp, Arthrobacter sp., Arthrobotrys oligospora, Aspergillus niger, Aspergillus sp., Azospirillum halopraeferans, Bacillus amyloliquefaciens, Bacillus atrophaeus, Bacillus circulans,Bacillus licheniformis, Bacillus subtilis, Burkholderia cepacia, Burkholderia vietnamiensis, Candida krissii,
  • Chryseomonas luteola Enterobacter aerogenes, Enterobacter asburiae, Enterobacter sp., Enterobacter taylorae, Eupenicillium parvum,
  • Exiguobacterium sp. Klebsiella sp., Kluyvera cryocrescens, Microbacterium sp., Mucor ramosissimus, Paecilomyces hepialid,
  • Paecilomyces marquandii Paenibacillus macerans, Paenibacillus mucilaginosus, Pantoea aglomerans, Penicillium expansum,
  • microorganism is a strain of the fungus Penicillium. Strains of the fungus Penicillium that may be useful in the practice of the present disclosure include P. bilaiae (formerly known as P. bilaii), P. albidum, P.
  • aurantiogriseum P. chrysogenum, P. citreonigrum, P. citrinum, P.
  • griseofulvum P. implicatum, P. janthinellum, P. Iilacinum, P. minioluteum, P. montanense, P. nigricans, P. oxalicum, P. pinetorum, P. pinophilum, P. purpurogenum, P. radicans, P. radicum, P. raistrickii, P. rugulosum, P. simplicissimum, P. solitum, P. variabile, P. velutinum, P. viridicatum, P. glaucum, P. fussiporus, and P. expansum.
  • the Penicillium species is P.
  • the P. bilaiae strains are selected from the group consisting of American Type Culture Collection (ATCC) ATCC 20851 , Northern Regional Research Laboratory (NRRL) NRRL 50169, ATCC 22348, ATCC 18309, NRRL 50162 (Wakelin, et al., 2004. Biol Fertil Soils 40:36-43).
  • ATCC American Type Culture Collection
  • NRRL Northern Regional Research Laboratory
  • NRRL 50169 ATCC 223408
  • ATCC 18309 ATCC 223408
  • NRRL 50162 Altschul, et al., 2004. Biol Fertil Soils 40:36-43
  • the Penicillium species is P. gaestrivorus, e.g., NRRL 50170 (see, Wakelin, supra.).
  • more than one phosphate solubilizing microorganism is used, for example, at least two, at least three, at least four, at least five, at least 6, including, for example, any combination of the Acinetobacter, Arthrobacter, Arthrobotrys, Aspergillus, Azospirillum, Bacillus, Burkholderia, Candida Chryseomonas, Enterobacter,
  • Paecilomyces hepialid Paecilomyces marquandii, Paenibacillus macerans, Paenibacillus mucilaginosus, Pantoea aglomerans, Penicillium expansum, Pseudomonas corrugate, Pseudomonas fluorescens,
  • Pseudomonas stutzeri Pseudomonas trivialis, Serratia marcescens, Stenotrophomonas maltophilia, Streptomyces sp., Streptosporangium sp., Swaminathania salitolerans, Thiobacillus ferrooxidans, Torulospora globosa, Vibrio proteolytics, Xanthobacter agilis, and Xanthomonas campestris.
  • two different strains of the same species may also be combined, for example, at least two different strains of Penicillium are used.
  • the use of a combination of at least two different Penicillium strains has the following advantages. When applied to soil already containing insoluble (or sparingly soluble) phosphates, the use of the combined fungal strains will result in an increase in the amount of phosphorus available for plant uptake compared to the use of only one Penicillium strain. This in turn may result in an increase in phosphate uptake and/or an increase in yield of plants grown in the soil compared to use of individual strains alone.
  • the combination of strains also enables insoluble rock phosphates to be used as an effective fertilizer for soils which have inadequate amounts of available phosphorus.
  • one strain of P. bilaiae and one strain of P. gaestrivorus are used.
  • the two strains are NRRL 50169 and NRRL 50162.
  • the at least two strains are NRRL 50169 and NRRL 50170.
  • the at least two strains are NRRL 50162 and NRRL 50170.
  • the phosphate solubilizing microorganisms may be prepared using any suitable method known to the person skilled in the art, such as, solid state or liquid fermentation using a suitable carbon source. These culture methods may be used in the preparation of an inoculum of Penicillium spp. for treating seeds and/or application to an agrononnically acceptable carrier to be applied to soil.
  • the term "inoculum” as used in this specification is intended to mean any form of phosphate solubilizing microorganism, fungus cells, mycelium or spores, bacterial cells or bacterial spores, which is capable of propagating on or in the soil, including on or in the vicinity of plant roots when the conditions of temperature, moisture, etc., are favorable for fungal growth.
  • the phosphate solubilizing microorganism is preferably prepared in the form of a stable spore.
  • Solid state production of Penicillium spores may be achieved by inoculating a solid medium such as a peat or vermiculite-based substrate, seeds or grains including, but not limited to, corn, soy, potato, oats, wheat, barley, or rice.
  • the sterilized medium (achieved through autoclaving or irradiation) is inoculated with a spore suspension comprising in the range of from 1 x10 2 -1 x10 7 colony forming units per milliliter (cfu/ml) of the appropriate Penicillium spp. and the moisture adjusted to 20 to 50%, depending on the substrate.
  • the inoculated medium is incubated for 2 to 8 weeks at room temperature.
  • the spores may also be produced by liquid fermentation (Cunningham et ai, 1990. Can J Bot. 68:2270-2274). Liquid production may be achieved by cultivating the fungus in any suitable media, such as potato dextrose broth or sucrose yeast extract media, under appropriate pH and temperature conditions that may be determined in accordance with standard procedures in the art.
  • the resulting material may be used directly, or the spores may be harvested, concentrated by centrifugation, formulated, and then dried using air drying, freeze drying, or fluid bed drying techniques (Friesen, et a/., 2005, Appl. Microbiol. Biotechnol. 68:397-404) to produce a wettable powder.
  • the wettable powder is then suspended in water, applied to the surface of seeds, and allowed to dry prior to planting.
  • the wettable powder may be used in conjunction with other seed treatments, such as, but not limited to, chemical seed treatments, carriers (for example, talc, clay, kaolin, silica gel, kaolinite) or polymers (for example, methylcellulose, polyvinylpyrrolidone).
  • a spore suspension of the appropriate Penicillium spp. may be applied to a suitable soil-compatible carrier (for example, peat-based powder or granule) to appropriate final moisture content.
  • a suitable soil-compatible carrier for example, peat-based powder or granule
  • the material may be incubated at room temperature, typically for about 1 day to about 8 weeks, prior to use.
  • the amount of the at least one phosphate solubilizing microorganism varies depending on the type of seed or soil, the type of plant material, the amounts of the source of phosphorus and/or micronutrients present in the soil or added thereto, etc. A suitable amount can be found by simple trial and error experiments for each particular case. Normally, for Penicillium, for example, the application amount falls into the range of from 0.001 to 1 .0 Kg fungal spores and mycelium (fresh weight) per hectare, or 10 2 -10 6 colony forming units (cfu) per seed (when coated seeds are used), or on a granular carrier applying between 1 x10 6 and 1 x10 11 colony forming units per hectare.
  • the fungal cells in the form of e.g., spores and the carrier can be added to a seed row of the soil at the root level or can be used to coat seeds prior to planting.
  • Diazotrophs are bacteria and archaea that fix atmospheric nitrogen gas into a more usable form such as ammonia.
  • Examples of diazotrophs include bacteria from the genera Rhizobium spp. (e.g., R. cellulosilyticum, R. daejeonense, R. etli, R. galegae, R. gallicum, R. giardinii, R.
  • loessense loessense, R. lupini, R. lusitanum, R. meliloti, R. mongolense, R.
  • miluonense R. sullae, R. tropici, R. undicola, and/or R. yanglingense
  • Bradyrhizobium spp. e.g., B. bete, B. canariense, B. elkanii, B.
  • iriomotense B. japonicum, B. jicamae, B. liaoningense, B. pachyrhizi, and/or B. yuanmingense
  • Azorhizobium spp. e.g., A. caulinodans and/or A. doebereinerae
  • Sinorhizobium spp. e.g., S. abri, S. adhaerens, S. americanum, S. aborts, S. fredii, S. indiaense, S. kostiense, S. kummerowiae, S. medicae, S. meliloti, S. mexicanus, S.
  • the diazotroph is selected from the group consisting of B. japonicum, R leguminosarum, R meliloti, S. meliloti, and combinations thereof.
  • the diazotroph is B. japonicum. In another embodiment, the diazotroph is R leguminosarum. In another embodiment, the diazotroph is R meliloti. In another embodiment, the diazotroph is S. meliloti.
  • Mycorrhizal fungi form symbiotic associations with the roots of a vascular plant, and provide, e.g., absorptive capacity for water and mineral nutrients due to the comparatively large surface area of mycelium.
  • Mycorrhizal fungi include endomycorrhizal fungi (also called vesicular arbuscular mycorrhizae, VAMs, arbuscular mycorrhizae, or AMs), an ectomycorrhizal fungi, or a combination thereof.
  • the mycorrhizal fungi is an endomycorrhizae of the phylum Glomeromycota and genera Glomus and Gigaspora.
  • the endomycorrhizae is a strain of Glomus aggregatum, Glomus brasilianum, Glomus clarum, Glomus deserticola, Glomus etunicatum, Glomus fasciculatum, Glomus intraradices, Glomus monosporum, or Glomus mosseae, Gigaspora margarita, or a combination thereof.
  • mycorrhizal fungi examples include ectomycorrhizae of the phylum Basidiomycota, Ascomycota, and Zygomycota.
  • Other examples include a strain of Laccaria bicolor, Laccaria laccata, Pisolithus tinctorius,
  • Rhizopogon amylopogon Rhizopogon fulvigleba, Rhizopogon luteolus, Rhizopogon villosuli, Scleroderma cepa, Scleroderma citrinum, or a combination thereof.
  • the mycorrhizal fungi include ecroid mycorrhizae, arbutoid
  • mycorrhizae or monotropoid mycorrhizae. Arbuscular and
  • the mycorrhiza may be an ericoid mycorrhiza, preferably of the phylum Ascomycota, such as
  • the mycorrhiza also may be an arbutoid mycorrhiza, preferably of the phylum Basidiomycota.
  • the mycorrhiza may be a monotripoid mycorrhiza, preferably of the phylum Basidiomycota.
  • the mycorrhiza may be an orchid mycorrhiza, preferably of the genus Rhizoctonia.
  • the agricultural compositions can comprise combinations of any of the above listed components.
  • the agricultural composition can comprise a combination of two different insecticides, a fungicide and any one or more of the above listed bacterial or fungal strains.
  • the agricultural composition can comprise the substantially pure compounds of Structure A and
  • chlorantraniliprole cyantraniliprole or a combination of chlorantraniliprole and cyantraniliprole and one or more of the ingredients in Table 1 of rows 1 , 2 or 3.
  • the agricultural composition can be applied by such methods as drenching the growing medium including a propagating material with a solution or dispersion of the agricultural composition, mixing the agricultural composition with growing medium and planting a propagating material in the treated growing medium (e.g., nursery box treatments), or various methods of propagating material treatment whereby the agricultural composition is applied to a propagating material before it is planted in a growing medium.
  • the formulation needs to provide the substantially pure Structure A compound, generally after dilution with water, in solution or as particles small enough to remain dispersed in the liquid.
  • Water-dispersible or soluble powders, granules, tablets, emulsifiable concentrates, aqueous suspension concentrates and the like are formulations suitable for aqueous drenches of growing media.
  • Drenches are most satisfactory for treating growing media that have relatively high porosity, such as light soils or artificial growing medium comprising porous materials such as peat moss, perlite, vermiculite and the like.
  • the drench liquid comprising the substantially pure Structure A compound can also be added to a liquid growing medium (i.e.
  • substantially pure Structure A compound which causes the substantially pure Structure A compound to become part of the liquid growing medium.
  • amount of substantially pure Structure A compound needed in the drench liquid for efficacy i.e. biologically effective amount
  • plant species i.e. plant species, propagating material type and environmental conditions.
  • concentration of substantially pure Structure A compound in the drench liquid is generally between about 10 "3 M to 10 "12 M of the composition, more typically between about 10 "6 M to 10 "10 M.
  • concentration of substantially pure Structure A compound in the drench liquid is generally between about 10 "3 M to 10 "12 M of the composition, more typically between about 10 "6 M to 10 "10 M.
  • One skilled in the art can easily determine the biologically effective concentration necessary for the desired level of efficacy.
  • a substantially pure Structure A compound can also be applied by mixing it as a dry powder or granule formulation with the growing medium. Because this method of application does not require first dispersing or dissolving in water, the dry powder or granule formulations need not be highly dispersible or soluble. While in a nursery box the entire body of growing medium may be treated, in an agricultural field only the soil in the vicinity of the propagating material is typically treated for environmental and cost reasons. To minimize application effort and expense, a formulation comprising the substantially pure Structure A compound is most efficiently applied concurrently with propagating material planting (e.g., seeding). For in-furrow application, the substantially pure Structure A formulation (most conveniently a granule formulation) is applied directly behind the planter shoe.
  • the substantially pure Structure A formulation is applied in a band over the row behind the planter shoe and behind or usually in front of the press wheel.
  • amount of substantially pure Structure A compound needed in the growing medium locus for efficacy i.e. biologically effective amount
  • concentration of substantially pure Structure A compound in the growing medium locus is generally between about 10 "3 M to 10 "12 M of the composition, more typically between about 10 "6 M to 10 "10 M.
  • biologically effective amount necessary for the desired level efficacy.
  • a propagating material can be directly treated by soaking it in a solution or dispersion of the substantially pure Structure A compound.
  • this application method is useful for propagating materials of all types, treatment of large seeds (e.g., having a mean diameter of at least 3 mm) is more effective than treatment of small seeds for providing efficacy.
  • Treatment of propagating materials such as tubers, bulbs, corms, rhizomes and stem and leaf cuttings can also provide effective treatment of the developing plant in addition to the propagating material.
  • the formulations useful for growing-medium drenches are generally also useful for soaking treatments.
  • the soaking medium comprises a nonphytotoxic liquid, generally water-based although it may contain nonphytotoxic amounts of other solvents such as methanol, ethanol, isopropanol, ethylene glycol, propylene glycol, propylene carbonate, benzyl alcohol, dibasic esters, acetone, methyl acetate, ethyl acetate, cyclohexanone, dimethylsulfoxide and /V-methylpyrrolidone, which may be useful for enhancing solubility of the substantially pure Structure A compound and penetration into the propagating material.
  • a surfactant can facilitate wetting of the propagating material and penetration of the substantially pure Structure A compound.
  • substantially pure Structure A compound needed in the soaking medium for efficacy i.e. biologically effective amount
  • the concentration of substantially pure Structure A compound in the soaking liquid is generally between about 10 "5 M to10 "12 M of the composition, more typically between about 10 "6 M to 10 "10 M.
  • the soaking time can vary from one minute to one day or even longer. Indeed, the propagating material can remain in the treatment liquid while it is germinating or sprouting (e.g., sprouting of rice seeds prior to direct seeding).
  • a propagating material can also be coated with a coating
  • composition comprising a biologically effective amount of the substantially pure Structure A compound.
  • the coatings of the disclosure are capable of affecting a slow release of the substantially pure Structure A compound by diffusion into the propagating material and surrounding medium.
  • Coatings include dry dusts or powders adhering to the propagating material by action of an adhesive agent such as methylcellulose or gum arabic.
  • Coatings can also be prepared from suspension concentrates, water- dispersible powders or emulsions that are suspended in water, sprayed on the propagating material in a tumbling device and then dried.
  • Substantially pure Structure A compounds that are dissolved in the solvent can be sprayed on the tumbling propagating material and the solvent then evaporated.
  • Such compositions preferably include ingredients promoting adhesion of the coating to the propagating material.
  • the compositions may also contain surfactants promoting wetting of the propagating material.
  • Solvents used must not be phytotoxic to the propagating material; generally water is used, but other volatile solvents with low phytotoxicity such as methanol, ethanol, methyl acetate, ethyl acetate, acetone, etc. may be employed alone or in combination. Volatile solvents are those with a normal boiling point less than about 100 °C. Drying must be conducted in a way not to injure the propagating material or induce premature germination or sprouting.
  • the thickness of coatings can vary from adhering dusts to thin films to pellet layers about 0.5 to 5 mm thick.
  • Propagating material coatings can comprise more than one adhering layer, only one of which need comprise the substantially pure Structure A compound.
  • pellets are most satisfactory for small seeds, because their ability to provide a biologically effective amount of the substantially pure Structure A compound is not limited by the surface area of the seed, and pelleting small seeds also facilitates seed transfer and planting operations. Because of their larger size and surface area, large seeds and bulbs, tubers, corms and rhizomes and their viable cuttings are generally not pelleted, but instead coated with powders or thin films.
  • Propagating materials contacted with agricultural compositions comprising substantially pure compounds of Structure A in accordance to this disclosure include seeds.
  • the application of the agricultural composition to seeds can accelerate the rate of germination.
  • Suitable seeds include seeds of wheat, durum wheat, barley, oat, rye, maize (corn), sorghum, rice, wild rice, cotton, flax, sunflower, soybean, garden bean, lima bean, broad bean, garden pea, peanut, alfalfa, beet, garden lettuce, rapeseed, cole crop, turnip, leaf mustard, black mustard, tomato, potato, pepper, eggplant, tobacco, cucumber, muskmelon, watermelon, squash, carrot, zinnia, cosmos, chrysanthemum, sweet scabious, snapdragon, gerbera, babys-breath, statice, blazing star, lisianthus, yarrow, marigold, pansy, impatiens, petunia, geranium and cole
  • Propagating materials contacted with substantially pure compounds of Structure A in accordance to this disclosure also include, for example, rhizomes, tubers, bulbs or corms, or viable divisions thereof.
  • Suitable rhizomes, tubers, bulbs and corms, or viable divisions thereof include those of potato, sweet potato, yam, garden onion, tulip, gladiolus, lily, narcissus, dahlia, iris, crocus, anemone, hyacinth, grape-hyacinth, freesia, ornamental onion, wood-sorrel, squill, cyclamen, glory-of-the-snow, striped squill, calla lily, gloxinia and tuberous begonia.
  • Propagating materials contacted with substantially pure compounds of Structure A can also include stems and leaf cuttings.
  • a propagating material is contacted with a coating composition comprising the substantially pure Structure A
  • compositions which comprise a biologically effective amount of the substantially pure compound of Structure A and a film former or adhesive agent, can further comprise an effective amount of at least one of the previously mentioned biologically active compounds or agents.
  • compositions comprising (in addition to the substantially pure Structure A compound and the film former or adhesive agent) arthropodicides of the group
  • pyrethroids such as cypermethrin, cyhalothrin, cyfluthrin and beta- cyfluthrin, esfenvalerate, fenvalerate and tralomethrin; carbamates such as fenothicarb, methomyl, oxamyl and thiodicarb; neonicotinoids such as clothianidin, imidacloprid and thiacloprid; neuronal sodium channel blockers such as indoxacarb; insecticidal macrocyclic lactones such as spinosad, abamectin, avermectin and emamectin; ⁇ -aminobutyric acid (GABA) antagonists such as endosulfan, ethiprole and fipronil; insecticidal ureas such as flufenoxuron and triflumuron; and juvenile hormone mimics such as diofenolan and pyr
  • the coating composition may further comprise formulation aids such as a dispersant, a surfactant, a carrier and optionally an antifoam agent and a dye.
  • formulation aids such as a dispersant, a surfactant, a carrier and optionally an antifoam agent and a dye.
  • the film former or adhesive agent component of the propagating material coating is composed preferably of an adhesive polymer that may be natural or synthetic and is without phytotoxic effect on the propagating material to be coated.
  • the film former or sticking agent may be selected from polyvinyl acetates, polyvinyl acetate copolymers, hydrolyzed polyvinyl acetates, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers, polyvinyl methyl ether, polyvinyl methyl ether-maleic anhydride copolymer, waxes, latex polymers, celluloses including ethylcelluloses and methylcelluloses, hydroxymethylcelluloses, hydroxypropylcellulose, hydroxymethylpropylcelluloses, polyvinylpyrrolidones, alginates, dextrins, malto-dextrins, polysaccharides, fats, oils, proteins, karaya gum, jagu
  • lignosulfonates acrylic copolymers, starches, polyvinylacrylates, zeins, gelatin, carboxymethylcellulose, chitosan, polyethylene oxide, acrylimide polymers and copolymers, polyhydroxyethyl acrylate, methylacrylimide monomers, alginate, ethylcellulose, polychloroprene and syrups or mixtures thereof.
  • Preferred film formers and adhesive agents include polymers and copolymers of vinyl acetate, polyvinylpyrrolidone-vinyl acetate copolymer and water-soluble waxes. Particularly preferred are polyvinylpyrrolidone-vinyl acetate copolymers and water-soluble waxes.
  • the above-identified polymers include those known in the art and for example some are identified as AGRIMER ® VA 6 (Vinylpyrrolidone/vinyl acetate copolymers available from Ashland, Inc., Covington, KY) and LICOWAX ® KST (an ester of montanic acids with multifunctional alcohols available from Clariant International Ltd., Muttenz, Switzerland).
  • the amount of film former or adhesive agent in the formulation is generally in the range of about 0.001 to 100% of the weight of the propagating material. For large seeds the amount of film former or adhesive agent is typically in the range of about 0.05 to 5% of the seed weight; for small seeds the amount is typically in the range of about 1 to 100%, but can be greater than 100% of seed weight in pelleting. For other propagating materials the amount of film former or adhesive agent is typically in the range of 0.001 to 2% of the propagating material weight.
  • formulation aids may also be used in propagating material treatment coatings are well known to those skilled in the art.
  • Formulation aids assist in the production or process of propagating material treatment and include, but are not limited, to dispersants, surfactants, carriers, antifoams and dyes.
  • Useful dispersants can include highly water-soluble anionic surfactants like BORRESPERSETM CA (a spray dried calcium lignosulphonate available from Borregaard
  • Useful surfactants can include highly water-soluble nonionic surfactants like PLURONIC ® F108 (a difunctional block copolymer surfactant available from BASF, Florham Park, NJ), BRIJ ® 78
  • Useful carriers can include liquids like water and oils which are water-soluble such as alcohols. Useful carriers can also include fillers like woodflours, clays, activated carbon, diatomaceous earth, fine-grain inorganic solids, calcium carbonate and the like. Clays and inorganic solids which may be used include calcium bentonite, kaolin, china clay, talc, perlite, mica, vermiculite, silicas, quartz powder, montmorillonite and mixtures thereof.
  • Antifoam agnets can include water dispersible liquids comprising polyorganic siloxanes like RHODORSIL ® 416 (mixture of silicone-polyether block copolymer and free polyether available from Rhodia Inc., Cranbury, NJ).
  • Dyes can include water dispersible liquid colorant compositions like PRO-IZED ® Colorant Red (liquid seed colorant available from Gustafson LLC, Piano, TX).
  • formulation aids include those listed herein and those listed in
  • the amount of formulation aids used may vary, but generally the weight of the components will be in the range of about 0.001 to 10000% of the propagating material weight, with the percentages above 100% being mainly used for pelleting small seed.
  • the amount of formulating aids is about 0.01 to 45% of the seed weight and typically about 0.1 to 15% of the seed weight.
  • the amount of formulation aids generally is about 0.001 to 10% of the propagating material weight.
  • Dusts or powders may be applied by tumbling the propagating material with a formulation comprising the substantially pure Structure A compound and a sticking agent to cause the dust or powder to adhere to the propagating material and not fall off during packaging or transportation. Dusts or powders can also be applied by adding the dust or powder directly to the tumbling bed of propagating materials, followed by spraying a carrier liquid onto the seed and drying. Dusts and powders comprising the substantially pure Structure A compound can also be applied by treating (e.g., dipping) at least a portion of the propagating material with a solvent such as water, optionally comprising a sticking agent, and dipping the treated portion into a supply of the dry dust or powder.
  • a solvent such as water
  • Propagating materials can also be dipped into compositions comprising Structure A formulations of wetted powders, solutions, suspoemulsions, emulfiable concentrates and emulsions in water, and then dried or directly planted in the growing medium.
  • Propagating materials such as bulbs, tubers, corms and rhizomes typically need only a single coating layer to provide a biologically effective amount of the substantially pure Structure A compound.
  • Propagating materials may also be coated by spraying a suspension concentrate directly into a tumbling bed of propagating materials and then drying the propagating materials.
  • other formulation types like wetted powders, solutions, suspoemulsions, emulsifiable concentrates and emulsions in water may be sprayed on the propagating materials. This process is particularly useful for applying film coatings to seeds.
  • Various coating machines and processes are available to one skilled in the art. Suitable processes include those listed in P. Kosters et al., Seed
  • Propagating materials such as seeds may be presized prior to coating. After coating the propagating materials are dried and then optionally sized by transfer to a sizing machine. These machines are known in the art for example, as a typical machine used when sizing corn (maize) seed in the industry.
  • the seed and coating material are mixed in any variety of conventional seed coating apparatus.
  • the rate of rolling and coating application depends upon the seed.
  • a satisfactory seed coating apparatus comprises a rotating type pan with lifting vanes turned at sufficient rpm to maintain a rolling action of the seed, facilitating uniform coverage.
  • the seed coating must be applied over sufficient time to allow drying to minimize clumping of the seed.
  • forced air or heated forced air can facilitate an increased rate of application.
  • this process may be a batch or continuous process. As the name implies, a continuous process allows the seeds to flow continuously throughout the product run. New seeds enter the pan in a steady stream to replace coated seeds exiting the pan.
  • the seed coating process of the present disclosure is not limited to thin film coating and may also include seed pelleting.
  • the pelleting process typically increases the seed weight from 2 to 100 times and can be used to also improve the shape of the seed for use in mechanical seeders.
  • Pelleting compositions generally contain a solid diluent, which is typically an insoluble particulate material, such as clay, ground limestone, powdered silica, etc., to provide bulk in addition to the film former such as one or more of those previously mentioned. After sufficient layers have been built up, the coat is dried and the pellets graded. A method for producing pellets is described in Agrow, The Seed Treatment Market, Chapter 3, PJB Publications Ltd., 1994.
  • Seed varieties and seeds with specific transgenic traits may be tested to determine which seed treatment options and application rates may complement such varieties and transgenic traits in order to increase rate of germination, increase rate of seedling emergence, increase rate of radicle growth, increase rate of early growth, increase pest control, increase disease control, increase plant height, increase vigor, increase resistance to abiotic environmental stress, and increase biomass and/or yield. Further, the good root establishment and early emergence that results from the proper use of the substantially pure compound of
  • Structure A seed treatment may result in more efficient nitrogen use, a better ability to withstand drought and an overall increase in yield potential of a variety or varieties containing a certain trait when combined with a seed treatment comprising the substantially pure compound of Structure A.
  • the agricultural composition is a foliar formulation.
  • Such formulations will generally include at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serve as a carrier.
  • the formulation ingredients are selected to be consistent with the physical properties of the substantially pure compound of Structure A, mode of application and environmental factors such as soil type, moisture and temperature.
  • Liquid compositions include solutions (including emulsifiable
  • aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion and suspoemulsion.
  • nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
  • solid formulations are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible (“wettable”) or water-soluble.
  • Substantially pure compounds of Structure A can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the substantially pure compound of
  • An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation.
  • High-strength compositions are primarily used as intermediates for further formulation.
  • Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water. Spray volumes can range from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry
  • formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.
  • Liquid and solid formulations can be applied onto seeds of crops and other desirable vegetation as seed treatments before planting to protect developing roots and other
  • Effective foliar formulations will typically contain from about 10 "5 M to 10 "12 M of the substantially pure compound of Structure A. In a preferred embodiment, formulations contain from about 10 "6 M to 10 "10 M of the substantially pure compound of Structure A.
  • the composition is applied to soil either prior to or following planting of propagating materials.
  • compositions can be applied as a soil drench of a liquid formulation, a granular formulation to the soil, a nursery box treatment or a dip of transplants.
  • the composition comprising the substantially pure compound of Structure A is applied to the soil in the form of a soil drench liquid formulation.
  • Other methods of contact include application of a compound or the agricultural composition by direct and residual sprays, aerial sprays, gels, seed coatings, microencapsulations, systemic uptake, foggers, fumigants, aerosols, dusts and many others.
  • One embodiment of a method of contact is a dimensionally stable fertilizer granule, stick or tablet comprising the substantially pure compound of Structure A.
  • Effective soil formulations will typically contain from about 10 " 5 M to 10 "12 M of the substantially pure compound of Structure A. In a preferred embodiment, formulations contain from about 10 "6 M to 10 "10 M of the substantially pure compound of Structure A.
  • Seeds that can be treated include, for example, wheat (Triticum aestivum L), durum wheat (Triticum durum Desf.), barley (Hordeum vulgare L), oat (Avena sativa L), rye (Secale cereale L), maize (Zea mays L), sorghum (Sorghum vulgare Pers.), rice (Oryza sativa L), wild rice (Zizania aquatica L), millet
  • cole crops such as cabbage, cauliflower and broccoli (Brassica oleracea L), turnip (Brassica rapa L), leaf (oriental) mustard (Brassica juncea Coss.), black mustard (Brassica nigra Koch), tomato (Lycopersicon esculentum Mill.), potato (Solanum tuberosum L), pepper (Capsicum frutescens L), eggplant (Solanum melongena L), tobacco (Nicotiana tabacum), cucumber
  • blazing star e.g., Liatris spicata Willd., L. pycnostachya Michx., L. scariosa Willd.
  • lisianthus e.g., Eustoma grandiflorum (Raf.) Shinn
  • yarrow e.g., Achillea filipendulina Lam., A. millefolium L
  • marigold e.g., Tagetes patula L, T. erecta L
  • pansy e.g., Viola cornuta L, V.
  • impatiens e.g., Impatiens balsamina L.
  • petunia Petunia spp.
  • geranium Geranium spp.
  • coleus e.g., Solenostemon scutellarioides (L.) Codd.
  • Gymnosperm seeds that can be treated include, for example, pine (Pinus spp.), fir (Abies, spp.), Hemlock (Tsuga spp.) cypress (Cupressus spp.) and Douglas-fir (Pseudotsuga spp.).
  • seeds, but also rhizomes, tubers, bulbs or corms, including viable cuttings thereof, can be treated according to the dislcosure from, for example, potato (Solanum tuberosum L), sweet potato (Ipomoea batatas L), yam (Dioscorea cayenensis Lam. and D.
  • crocus Crocus spp.
  • anemone Anemone spp.
  • hyacinth Hyacinth spp.
  • grape-hyacinth Muscari spp.
  • freesia e.g., Freesia refracta Klatt., F. armstrongii ⁇ N .
  • Wats ornamental onion (Allium spp.), wood-sorrel (Oxalis spp.), squill (Scilla peruviana L. and other species), cyclamen (Cyclamen persicum Mill, and other species), glory-of-the-snow (Chionodoxa luciliae Boiss. and other species), striped squill (Puschkinia scilloides Adams), calla lily (Zantedeschia aethiopica Spreng., Z. elliottiana Engler and other species), gloxinia (Sinnigia speciosa Benth. & Hook.) and tuberous begonia
  • Stem cuttings can include those from such plants as sugarcane (Saccharum officinarum L.), carnation (Dianthus caryophyllus L.), florists chrysanthemum (Chrysanthemum mortifolium Ramat.), begonia (Begonia spp.), geranium (Geranium spp.), coleus (e.g., Solenostemon scutellarioides (L.) Codd) and poinsettia (Euphorbia pulcherrima Willd.).
  • Leaf cuttings which can include those from begonia (Begonia spp.), african-violet (e.g., Saintpaulia ionantha Wendl.) and sedum (Sedum spp.).
  • preferred embodiments can include wheat, rice, maize, barley, sorghum, oats, rye, millet, soybeans, peanuts, beans, rapeseed, canola, sunflower, sugar cane, potatoes, sweet potatoes, cassava, sugar beets, tomatoes, plantains and bananas, and alfalfa.
  • D-Glucosamine hydrochloride (Product 1 , 1 .0 kg) was suspended in methanol (5.0 L) and vigorously stirred. NaOH (184.8 g) was dissolved in minimum deionized water and added to the D-glucosamine/methanol (MeOH) suspension. The suspension was stirred for 15 min and the insoluble material (sodium chloride) was filtered off by vacuum filtration.
  • phthalic anhydride (342 g) was added and the solution was stirred until most of the solid dissolved (about 30 min). This was then followed by addition of triethylamine (468 g) and stirring for 10 to 15 min. To the resulting clear solution, another portion of phthalic anhydride (342 g) was added and the mixture was allowed to stir overnight at room temperature. Product began to precipitate out after two hours. The precipitated product was filtered and the residue was washed with minimum ice cold methanol so as to remove the yellow color from the product. The residue was then washed three times with acetonitrile, with enough solvent added to the filter to completely immerse the solid, and dried at room temperature under high vacuum.
  • the weight of the white solid, Product 2 was 954 g.
  • the Product 2 from above (1 .01 Kg, made from two batches) was placed in a 10 L 3-neck round bottom flask set up with an overhead electric stirrer, an N 2 inlet and an addition funnel.
  • Acetic anhydride (3 L) and N,N-dimethylaminopyridine (1 .0 g) were added to the flask and stirred vigorously.
  • Pyridine (2.8 L) was added slowly and the reaction mixture was stirred for 2 days at room temperature.
  • the reaction mixture was quenched with ice-water (4 L) and the product was extracted with methylene chloride (CH2CI2).
  • CH2CI2CI2 methylene chloride
  • the organic layer was repeatedly washed with aqueous hydrochloric acid solution, and then with saturated sodium bicarbonate solution.
  • Product 3 (464 g) was dissolved in toluene and the solvent was evaporated. This was repeated and the remaining solid was placed on a high vacuum line overnight.
  • Product 4 (350 g) was suspended in nearly 4 L of dry methanol. To this, 35 ml of 0.5 M sodium methoxide solution was added and the solution immediately turned basic. The suspension was left stirring at room temperature overnight. The solid deposited was filtered and washed with dichloromethane, giving pure Product 5 (232 g). The filtrate was neutralized with sulfonic acid resin and concentrated to dryness. The dry solid was washed with CH 2 CI 2 and dried, giving impure Product 5 (43.8 g).
  • Product 5 (295 g; 638 mmol) was suspended in dry toluene (1 L) and evaporated under vacuum. This procedure was repeated once more to ensure the removal of methanol contaminant that is detrimental to the reaction. 265 grams total product was recovered. The residue after toluene evaporation was suspended in CH2CI2 (3 L) in a 3-neck flask fitted with an overhead stirrer and the suspension was stirred under dry nitrogen atmosphere. The flask was cooled in an ice bath and the following reagents were added: 126g pyridine, 500mg N,N-dimethylaminopyridine; and 171 g benzoyl chloride (slowly added by means of an addition funnel in drops over 60 min).
  • the reaction mixture was milky white, but began to clear when all of the benzoyl chloride was added.
  • the reaction was allowed to stir for 18 h at room temperature.
  • the reaction was diluted with CH2CI2 and was washed with water (2x), 1 M aqueous HCI (2x), then saturated NaHCO 3 and dried with MgSO .
  • Product 8 (crude; 105.3), after being evaporated with toluene-DMF, was suspended in CH 2 CI 2 (500 ml). Pyridine (61 .8 g; 782 mmol; 2.5 eq.) was added first, followed by the drop-wise addition of benzoyl chloride (88 g; 626 mmol; 2.0 eq.) to the mixture. The reaction mixture was allowed to stir at room temperature for 24 h. It was then diluted with CH 2 CI 2 and washed sequentially with H 2 O,1 M HCI (2X), then aqueous saturated sodium bicarbonate solution, dried with MgSO ⁇ filtered, and concentrated.
  • Pyridine 61 .8 g; 782 mmol; 2.5 eq.
  • benzoyl chloride 88 g; 626 mmol; 2.0 eq.
  • the product was purified by chromatography on silica gel, using 3:8 EtOAc-hexane as the eluant.
  • the weight of the purified product was 1 16.1 g.
  • the product was about 90% pure as determined by NMR.
  • a portion (21 .1 g) of this product was crystallized from diethylether-hexane to obtain pure crystalline material (13.8 g) of Monomer B.
  • Monomer A (80.6 g, 109.3 mmol, 1 .2 eq.) and Monomer B (48.4 g, 91 .1 mmol), both previously evaporated with toluene once, were dissolved in CH 2 CI 2 (150 ml_) in a 3-necked, 500 ml flask. 4A Molecular sieve was added (5 g). The mixture was cooled to -60° C under nitrogen atmosphere with vigorous stirring.
  • N-lodosuccinimide N-lodosuccinimide (NIS; 44.3 g; 196.7 mmol; 2.2 eq.) was added as a dry powder, followed by the dropwise addition of a solution of triflic acid (TfOH; 13.7 g, 91 .1 mmol, 1 .0 eq.) and methyltriflate (14.9 g, 54.8 mmol, 1 .0 eq.) in CH 2 CI 2 . The reaction mixture was left at -55° C for an additional 4 hr. An additional 100 ml of the triflic acid/methyltriflate solution was added to the reaction mixture dropwise to reduce of the viscosity.
  • TfOH triflic acid
  • methyltriflate 14.9 g, 54.8 mmol, 1 .0 eq.
  • reaction mixture was filtered cold over a celite pad into a filter flask containing 1 :1 saturated sodium thiosulfate-sodium bicarbonate solution that was stirred thoroughly during filtration.
  • the flask and residue on the filter were rinsed with CH 2 CI 2 and the combined filtrate was worked up as follows.
  • Product 9 (1 1 1 .1 g) was dissolved in THF (350 ml). To this solution, a 1 M solution of acetic acid (1 10 ml) and a 1 M solution of n- tetrabutylammonium fluoride in THF (1 10 ml) were added and the reaction mixture was stirred at room temperature for 3 days. Completion of the reaction was ascertained by TLC using EtOAC-HexEtOH (4:8:1 ) as a solvent, which indicated that the reaction was complete. The solvent of the reaction was evaporated on high vacuum (without heat) and the residue was dissolved in CH2CI2, washed sequentially with water, 1 M aqueous
  • Fraction B product had about 5% silicon impurity (peak around 0 ppm) along with the major desired disaccharide.
  • Fraction A was contaminated about 10% with tBDMS impurities and a tetrabutylammonium derivative. Therefore, Fraction A was resuspended in 600 ml of ether, mixed for about 10 minutes, filtered and the process was repeated once more (weight of the solid recovered was 77.3 g). This solid was purified once more by dissolving the product in EtOAc and precipitating the product with the aid of hexane (weight of the product recovered was 71 .7 g).
  • reaction mixture was poured over saturated NaHCOs and saturated sodium thiosulfate aqueous solution (1 :1 , 400 ml) contained in an Erlenmeyer flask and thoroughly stirred. Additional CH 2 CI 2 (200 ml) was added and the contents were thoroughly mixed for 10 min, the aqueous solution separated, and the organic layer washed with 0.6% aqueous bleach solution, deionized water, and aqueous saturated CH 2 CI 2 solution. The solution was then dried with MgS04, filtered and concentrated.
  • Product 1 1 was dissolved in minimum THF (500 ml). To this solution, 1 M solution of acetic acid (150 ml) and a 1 M solution of n- tetrabutylammonium fluoride in THF (150 ml) were added and the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was evaporated to dryness, the residue redissolved in CH 2 CI 2 , washed sequentially with deionized water, 1 M HCI, 1 % aqueous bleach solution (to remove the dark brown color), and saturated CH 2 CI 2 solution, then concentrated to dryness.
  • Polystyrene-ethylenediamine resin (26.0 g) was added and the slurry was heated to 105° C with stirring for 24 h. It was then filtered, concentrated to dryness, and the resulting material was redissolved in water and washed with CH 2 CI 2 . The aqueous layer was concentrated to dryness.
  • the trisaccharide Product 12 (6.1 g) was suspended in MeOH (300 ml), then NaOMe (0.5 M, 7 ml) was added and stirred at room temperature for 2 days. The mixture was then heated to 65° C for 24 h. Examination of the reaction mixture by proton NMR indicated that all benzoate groups had been removed. A white precipitate appeared in the reaction flask. The flask was cooled in an ice bath for 15 min and filtered. The filtrate was neutralized with acidic resin, and concentrated to dryness (Fraction B). The residue in the filter was washed with hot DMF and concentrated to dryness (Fraction A).
  • reaction mixture from Fraction B was filtered, washed and concentrated to dryness.
  • the yellow solid was dissolved in water and the aqueous layer was extracted twice with CH 2 CI 2 to remove the byproduct methyl benzoate. Finally, the aqueous layer was concentrated to dryness, the residue redissolved in water, and lyophilized (Fraction E).
  • NMR analysis of the Fraction E product indicated incomplete phthalimide removal.
  • the solid was suspended in n-butanol (100 ml) and heated to 104° C.
  • MR-Ethylenediamine resin (9 g) was added and the reaction was continued for two days.
  • Fraction F The NMR spectrum of Fraction F showed that though the major product was the desired triglucosamine Product 14, it was contaminated with some incompletely deprotected trisaccharide.
  • test compounds 25 ml_, 10 "7 M in Dl-water
  • a fungicide solution was added to each of the aqueous solutions of the test compounds.
  • Five Petri dishes and 100 seeds were used to test one composition. The seeds were inspected for uniformity and lack of cracks in the seed prior to use.
  • a piece of filter paper was used to cover the inner side of each Petri dish to allow uniform distribution of testing solution. Twenty seeds were placed on the filter paper area of one Petri dish. Each corn seed of examples 10 and 1 1 was placed on the filter paper with the flat side of the corn seed facing upwards.
  • the seeds were placed on the filter paper so that the seeds were not touching each other. 5 ml_ of the test compound solution was carefully poured in the Petri dish. Control experiments were set up the same way with 20 seeds and 5 ml_ of deionized water per dish without any active species. The lid was placed on the Petri dish and was sealed with Para-film. Five dishes with repeat experiments were stacked. Each stack of dishes was wrapped twice with aluminum foil to prevent the seeds receiving any light and the stacks were germinated in dark at the ambient laboratory conditions. The stacks were inspected after 24, 36, 48 and 60 hours. The number of germinated seeds was counted and the percent of germination on each dish was calculated. Radicle emergence was used as the germination indicator.
  • the dishes were placed unwrapped at room temperature for one day and the number of germinated seeds was counted to assure seeds were able to germinate and difference in germination yields were not caused by poor seed quality.
  • Statistical analyses were performed by calculating the standard deviation of the five repetitions for each
  • a seed coating composition was prepared comprising fungicide, insecticide, film forming binder, colorant, Product 14 (3 x 10 "7 M) and water.
  • a control coating was also prepared using the identical ingredients, but excluding Product 14.
  • Corn seeds were coated with the seed coating composition using spray treatment method. Five petri dishes and 100 seeds were used to test each seed coating composition. Each corn seed was inspected for uniformity and lack of cracks in the seeds prior to use. A piece of filter paper was used to cover the inner side of each petri dish to allow uniform distribution of water. Twenty corn seeds were placed on the filter paper area of one petri dish with the flat side of the corn seed facing upwards. The seeds were placed one the filter paper so that the corn seeds were not touching each other. 5 ml_ of water was added to each petri dish.
  • the dishes were sealed, stacked and placed in an incubator set to 10°C.
  • the dishes were examined twice per day at the times indicated in Table 3. During the observation period, one stack was removed from the incubator and observed for germination. The dishes were then rotated within the stack and placed back into the incubator before removing another treatment stack.
  • Table 1 shows the percent germination of corn seeds treated with diglucosamine Product 13 vs. control treatment maintained at room temperature at selected time points.
  • Corn seeds treated with aqueous solutions of Product 13 exhibited statistically significant increases in percent germination at 48 and 60 hours following treatment initiation compared to the control treatment (Table 1 ). Results were deemed statistically significant when the standard deviations (indicated in brackets) of the treatment averages do not overlap.
  • Table 2 shows the percent germination of corn seeds treated with triglucosamine Product 14 vs. control treatment maintained at room temperature at selected time points.
  • Corn seeds treated with aqueous solutions of Product 14 exhibited statistically significant increases in percent germination at 48 and 60 hours compared the control treatment (Table 2). Results were deemed statistically significant when the standard deviations (indicated in brackets) of the treatment averages do not overlap.
  • Table 4 shows the percent increase in percent germination of corn seed treated with triglucosamine Product 14 vs. control treatment and maintained under cold stress (10°C) at selected time points.
  • Soybean seeds treated with aqueous solutions of Product 13 and Product 14 exhibited statistically significant increases in percent

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Abstract

La présente invention concerne des formulations comprenant des oligoglucosamines synthétiques, et des procédés qui utilisent ces formulations pour améliorer la croissance des végétaux et le rendement des cultures. Ces formulations peuvent être appliquées sur du matériel de propagation de végétaux, y compris sur de la semence et sur d'autres parties de végétaux pouvant être régénérées, y compris des boutures, des bulbes, des rhizomes et des tubercules. Elles peuvent également être appliquées sur le feuillage ou sur le sol, avant ou après la plantation du matériel de propagation. De telles applications peuvent s'effectuer seules ou en combinaison avec des fongicides, des insecticides, des nématicides et d'autres agents agricoles utilisés pour améliorer la croissance des végétaux et le rendement des cultures.
PCT/US2015/017666 2014-02-28 2015-02-26 Oligoglucosamines synthétiques pour l'amélioration de la croissance et du rendement de végétaux WO2015130893A1 (fr)

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WO2016144688A1 (fr) * 2015-03-11 2016-09-15 Pioneer Hi Bred International Inc Combinaisons de pip-72 insecticides et procédés d'utilisation
US10667524B2 (en) 2013-09-13 2020-06-02 Pioneer Hi-Bred International, Inc. Insecticidal proteins and methods for their use

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US10667524B2 (en) 2013-09-13 2020-06-02 Pioneer Hi-Bred International, Inc. Insecticidal proteins and methods for their use
US11325949B2 (en) 2013-09-13 2022-05-10 Pioneer Hi-Bred International, Inc. Insecticidal proteins and methods for their use
WO2016144688A1 (fr) * 2015-03-11 2016-09-15 Pioneer Hi Bred International Inc Combinaisons de pip-72 insecticides et procédés d'utilisation
US10876132B2 (en) 2015-03-11 2020-12-29 Pioneer Hi-Bred International, Inc. Insecticidal combinations of PIP-72 and methods of use
EA038923B1 (ru) * 2015-03-11 2021-11-10 Пайонир Хай-Бред Интернэшнл, Инк. Инсектицидная днк-конструкция и способы её применения

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