WO2018210872A1 - Stilbènes destinés au traitement post-récolte et à la conservation de produits alimentaires et/ou au prolongement de la durée de conservation - Google Patents

Stilbènes destinés au traitement post-récolte et à la conservation de produits alimentaires et/ou au prolongement de la durée de conservation Download PDF

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WO2018210872A1
WO2018210872A1 PCT/EP2018/062607 EP2018062607W WO2018210872A1 WO 2018210872 A1 WO2018210872 A1 WO 2018210872A1 EP 2018062607 W EP2018062607 W EP 2018062607W WO 2018210872 A1 WO2018210872 A1 WO 2018210872A1
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ppm
resveratrol
stilbene
composition
composition according
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PCT/EP2018/062607
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English (en)
Inventor
William Hamilton
Joseph SHERIDAN
Ernesto SIMON VECILLA
Angela TSETSIS
Gomathi V ARUNAN
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Evolva Sa
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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
    • A01N27/00—Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system

Definitions

  • the present invention relates to novel harvested crop protection against fungal and/or bacterial infections.
  • the active ingredients according to the invention are distinguished by particularly good tolerance by plants and favorable ecological properties.
  • Plants produce substances known as phytoaiexins that accumulate rapidly at areas of pathogen infection as a natural defense in response to stress and to fight infections.
  • Resveratrol and its derivatives are examples phytoaiexins found in grapes, peanuts, cranberries, blueberries, strawberries, Polygonum cuspidatum and some other botanical sources. These plants produce resveratrol, resveratrol glycosides and other phenylpropanoid derivatives as a natural defense in response to stress and to fight infections.
  • the content of resveratrol and resveratrol glycoside increases in grapes in grapes increases upon infection with Botrytis cinerea (Roldan 2003).
  • Resveratrol and its derivatives have wide ranging biological activities and consequently many different targets and mechanisms of action.
  • resveratrol has been associated with the prevention or slow the progression of several diseases, including cardiovascular, metabolic and neurodegenerative diseases.
  • Resveratrol also has human antiinflammatory, antioxidant and antimicrobial properties against human microbial pathogens including yeast such as Candida (reviewed in Paulo 2011).
  • compositions and methods of their use are effective natural compositions and methods of their use in protection and treatment against fungal and/or bacterial infections and/or contaminations.
  • microbially-produced stilbenes (such as resveratrol and derivatives thereof) are useful in the protection against and treatment of microbial infections and/or contaminations.
  • the invention provides a method of preventing, treating, or reducing an infection by phytopathogenic, facultative saprophytic or saprotrophic microbes in a surface or subject to be treated, comprising contacting the surface or subject with a composition comprising a stilbene or a methylated or glycosylated derivative thereof.
  • the composition comprising a stilbene or methylated or glycosylated derivative thereof further comprises nootkatone.
  • the invention provides a composition for preventing, treating or reducing an infection by phytopathogenic, facultative saprophytic or saprotrophic microbes in a surface or subject to be treated, comprising a stilbene or a methylated or glycosylated derivative thereof.
  • the composition further comprises at least one additional active ingredient that is a fungicide, fungistatin, bactericide, bacteriostatin, or pesticide.
  • Embodiment 17 The method according to any of embodiments 1-16, wherein the method of application is spraying, atomizing, dusting, scattering, brushing on, submerging, dipping, coating, pouring, or rubbing.
  • Embodiment 37 The composition according to any of embodiments 34-36, wherein the at least one additional active ingredient is active against a phytopathogenic, facultative saprophytic, or saprotrophic yeast.
  • Embodiment 38 The composition according to any of embodiments 34-37, wherein the at least one additional active ingredient is active against a phytopathogenic, facultative saprophytic, or saprotrophic bacteria.
  • Embodiment 48 The composition according to any of embodiments 40-47, comprising: (a) at least about 0.0001%, at least about 0.001%, at least about 0.01%, at least about 0.1%), at least about 1%, at least about 2%, at least about 5%, at least about 7.5%, at least about 10%, at least about 15%, at least about 20%, at least about 25%, or at least about 50%) by weight stilbene; or (b) at least about 1 ppm, or at least about 10 ppm, or at least about 20 ppm, or at least about 25 ppm, or at least about 50 ppm, or at least about 62.5 ppm, or at least about 100 ppm, or at least about 125 ppm, or at least about 150 ppm, or at least about 200 ppm, or at least about 250 ppm, or at least about 500 ppm, or at least about 1 ,000 ppm, or at least about 5,000 ppm of the stilbene, or about 10 pp
  • Embodiment 52 The composition according to embodiment 50 or 51 , wherein the at least one additional active ingredient is active against a phytopathogenic, facultative saprophytic, or saprotrophic filamentous fungus.
  • Embodiment 53 The composition according to any of embodiments 50-52, wherein the at least one additional active ingredient is active against a phytopathogenic, facultative saprophytic, or saprotrophic yeast.
  • Embodiment 57 Use of the composition according to any of embodiments 27-39 for preventing, treating, or reducing an infection by phytopathogenic, facultative saprophytic, or saprotrophic microbes on a surface or object.
  • FIG.l illustrates a biosynthetic pathway for resveratrol.
  • FIG.3 shows the shows the names, molecular weights and aqueous solubilities of various resveratrol glycoside molecules.
  • FIG.10 illustrates Alternaria sp. spore germination at 24 hours under control conditions (control; scale bar is 20 microns) and treated with resveratrol alone at 125 ppm (RESV@125ppm; scale bar is 50 microns), the combination of resveratrol and nootkatone each at 125 ppm (RESV+NKT@125ppm; scale bar is 20 microns), the combination of resveratrol and nootkatone 62.5 ppm each (RESV+NKT@62.5ppm; scale bar is 20 microns), and carbendazim at lOppm (Carbendazim@10ppm; scale bar is 20 microns).
  • FIG.13 shows that higher concentrations (250 -500 ppm) of resveratrol inhibit B. cinerea growth in vitro after seven days of incubation.
  • FIG.14 shows that combinations of resveratrol and nootkatone inhibit B. cinerea growth in vitro after five days of incubation.
  • FIG.19 shows that various concentrations of resveratrol inhibit Colletotrichum gloeosporoides growth in vitro after six days of incubation.
  • FIG.20 shows that various concentrations of resveratrol inhibit Colletotrichum gloeosporoides growth in vitro after nine days of incubation.
  • FIG.22 shows that various concentrations of resveratrol inhibit Fusarium oxysporium growth in vitro after eleven days of incubation.
  • FIG.23 shows that various concentrations of resveratrol inhibit Trichothecium roseum growth in vitro after ten days of incubation.
  • FIG.24 shows that 62.5 ppm resveratrol prevents spore germination of Trichothecium roseum growth in vitro.
  • FIG.25 shows images of Monilinia laxa conidia, conidia stained with blue lactophenol blue, M. laxa in cherry, and front and back side views of M. laxa on PDA plates.
  • FIG.26A shows mycelial growth inhibition of M. laxa by treatment with nootkatone (NKT), or treatment the combination of resveratrol and nootkatone (RESV+NKT) at the concentrations shown (ppm) on PDA plates.
  • NKT nootkatone
  • RV+NKT treatment the combination of resveratrol and nootkatone
  • FIG.26C shows mycelial growth inhibition of M. laxa by resveratrol alone.
  • FIG.26D shows mycelial growth inhibition of M. laxa by resveratrol alone.
  • FIG.28 shows post-harvest management of fungal diseases and pathogens in sweet cherries by treatment with control, treatment with the combination of resveratrol and nootkatone at 50ppm each (RESV+NKT), treatment with resveratrol alone at 150ppm (RESV), and treatment with Amistar TOP ® (yellow circles indicate dryness and shrunk regions of cherries induced by Amistar TOP ® ).
  • FIG.29A shows that resveratrol is effect in controlling mycelial growth of Magnaporthe grisea on plates at 50ppm and 250ppm.
  • FIG.31 shows preservation of texture of mutton treated with resveratrol.
  • FIG.32 shows preservation of color of mutton treated with resveratrol.
  • FIG.33A shows a photograph of spore germination of Uncinula necator in control after 20 hours.
  • the terms “or” and “and/or” are utilized to describe multiple components in combination or exclusive of one another.
  • “x, y, and/or z” can refer to “x” alone, “y” alone, “z” alone, “x, y, and z,” “(x and y) or z,” “x or (y and z),” or “x or y or z.”
  • active ingredient refers to a chemical compound or mixture of chemical compounds capable of treatment of phytopathogenic microbes from any propagated plant, propagated plant material, or other surface, materials and substances disclosed herein.
  • the active ingredient may have properties including but not limited to antimicrobial, antibacterial, and/or antifungal properties against microbes capable of infecting, growing and reproducing on consumable products, plants, portions thereof, or propagated plant materials.
  • the active ingredients may be effective against phytopathogenic microbes including but not limited to microorganisms from the following classes: Ascomycetes (for example Glomerella, Trichothecium, Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula, Leotiomyceta, Botryodiplodia, Lasiodiplodia, Magnaporthe, Fusarium, P en ic ilium, Aspergillus); Basidiomycetes (for example the genera Hemileia, Rhizoctonia, Puccinia); Fungi imperfecti (for example Botrytis, Helminthosporium, Rhynchosporium, Septoria, Cercospora, Altern
  • the term "antimicrobial” is understood as being effective in preventing or reducing infection or extending the shelf-life of consumable products, propagated plants or propagated plant materials, plant fruit or plant seed by microscopic organisms such as phytopathogenic microbes or facultative saprophytic microbes.
  • the active ingredients may have antifungal and/or antibacterial effects.
  • antifungal is understood as being effective in preventing or reducing a fungal infection and includes fungicides that kill fungi or fungal spores, and fungistatics that inhibit the growth and/or reproduction of fungi.
  • antibacterial is understood as being effective in preventing or reducing a bacterial infection and includes bactericides that kill bacteria and bacteriostatics that inhibit the reproduction of bacteria.
  • phytopathogenic or saprophytic microscopic organisms and phytopathogenic microbes are used interchangeably and encompass, but are not limited to, fungi, bacteria, oomycetes, and phytoplasma that infect, grow and reproduce on consumable products, propagated plants, portions thereof, or propagated plant material.
  • phytopathogenic microbes may be pathogenic to propagated plants, may be lysotrophic, or may be facultative saprophytic capable of infecting stressed or dying propagated plants, possibly in combination with plant pathogens.
  • phytopathogenic, facultative saprophytic or saprotrophic microbes include but are not limited to microorganisms from the following classes: Ascomycetes (for example Glomerella, Colletotrichum, Trichothecium, Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula, Leotiomyceta, Botryodiplodia, Lasiodiplodia, Magnaporthe); Basidiomycetes (for example the genera Hemileia, Rhizoctonia, Puccinia); Fungi imperfecti (for example Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyricularia and, Pseudocercosporella herpotrichoides); Oomycetes (for example Phytophthora, Peronospora, Bremia, Pythium, Plasmopara); Firmicutes
  • treatments include applying a composition including resveratrol or derivative thereof (such as a methylated and/or glycosylated derivative of resveratrol).
  • Treatment of phytopathogenic microbes may include a second or subsequent treatment to prevent recovery of the population of phytopathogenic microbes.
  • the terms "surface” or "object to be treated” interchangeably refer to any consumable product, any propagated plant, portion of a propagated plant, propagated plant material, plant fruit or plant seed surface area and/or material that phytopathogenic microbes may attempt to infect, meat products, or are surfaces and objects which could act as vectors for the transportation of phytopathogenic microbes between infected and uninfected host consumable products, propagated plants, or propagated plant material.
  • consumable product includes any product that is consumable by humans and/or animals (for example, horses, cows, sheep, goats, chickens, dogs, or cats).
  • consumable products can include, but are not limited to all food products, food additives, nutraceuticals, pharmaceuticals (i.e, any product placed in the mouth), cereal products, rice products, tapioca products, bread products, meat and meat products, jellies, jams, egg products, milk and dairy products, cheese products, butter and butter substitute products, milk substitute products, soy products, edible oils and fat products, beverages, carbonated beverages, fruit drinks, fruit juices, beverage powder, milk based beverage powder, food extracts, plant extracts, meat extracts, and combinations thereof.
  • consumable products can include propagated plant materials or parts thereof (for example, hay, flour, wood, cotton, linen).
  • propagated plant includes any crop or plant that is deliberately sown, planted, transplanted, cultivated or nurtured by humans. It may refer, for example, to whole plants, field crops, fruit or nut trees, seedlings, young plants or plant seeds.
  • propagated plant material encompasses “material to be harvested”, “harvested material”, and the "commercially relevant portion of a crop or plant” and refers, for example, to plant extracts, shoots, sprouts, leaves, cuttings, roots, tubers, bulbs, rhizomes, grain, fruits, seeds, nuts, and flowers or other plant parts of cosmetic, aesthetic, or commercial value (for example lumber products or cotton or other natural textiles).
  • contemplated crops include but are not limited to mushrooms, fruit trees and fruit plants (citrus fruit trees, lemon trees, lime trees, orange trees, grapefruit trees, apple trees, apricot trees, pear trees, plum trees, cherry trees, grape vines, nectarine trees, peach trees, tangerine trees, raspberry canes, blueberry bushes, pineapple plants, banana trees, strawberry plants, tomato plants, pepper plants, chili bushes), cereal crops (wheat, barley, rye, oats, hay, rice, quinoa, millet, sorghum and related species); beet (sugar and fodder beet); leguminous plants (beans, lentils, peas, soya beans); oil crops (oilseed rape, mustard, poppies, olive trees, sunflower plants, coconut trees, castor plants, cocoa trees, groundnuts, oil palms); cucurbits (pumpkin plants, cucumber plants, melon plants); fiber plants (cotton, flax, hemp, j
  • Such areas and environments include, but are not limited to, an agricultural field, a field of crops, an arable field, a greenhouse, an orchard, a polytunnel, an area for mushroom cultivation, an area of commercial flower cultivation, a commercial forest, a hydroponics facility, parks, gardens, flower shows, and indoor or outdoor storage areas for propagated plants or propagated plant material, plant fruit or plant seed, including but not limited to a granary, a flower shop, a potato shed, a food processing factory, a meat processing facility, a warehouse, or containers used to transport or store propagated plant material, including but not limited to bags, boxes, crates, nets, jars, tubs, sacks, silos, presses, Archimedes screws, hoppers, conveyor belts, trailers, storage bins, refrigerators, freezers, packaging material, or plastic wrap.
  • shelf-life is defined in the context of storage, at ambient or refrigerated temperature, and typically refers to the maximum time for which consumable products can be stored, during which the defined quality of a specified proportion of the goods remains acceptable under expected conditions of distribution, storage, and display.
  • ambient temperature means any temperature within a range commonly occurring in the interior of warehouse or storage facilities or retail settings, for example about 15°C to about 25°C.
  • refrigerated temperature means any temperature within a range commonly occurring in the interior of a refrigerator or freezer, for example about -20°C to about 15°C, typically about 4 °C in a refrigerator and typically about -20°C in a freezer.
  • Examples of the defined quality to be maintained during storage may include, but are not limited to, appearance (such as colour retention, reduced browning, limited visible signs of microbial growth, limited surface wrinkling), consistency (such as retention of firmness, lack of phase separation, limited drip-loss, no change in mouthfeel), flavour (such as freshness of flavours for which the consumable product is associated, limited development of bitter flavours or flavours associated with oxidation or microbial growth). It will be understood that storage at higher temperatures can be expected to shorten shelf-life and at lower temperatures to prolong shelf-life.
  • the methods and compositions disclosed herein can extend the shelf-life of a consumable product by about 1 day, about 2 days, about 3 days, about 4 days, about 5 days, about 6 days, about 7 days or more; or by about 1 week, about 2 weeks, about 3 weeks, about 4 weeks, about 5 weeks, about 6 weeks, about 7 weeks, about 8 weeks, about 9 weeks, about 10 weeks, about 11 weeks, about 12 weeks or more; or by about 1 month, about 2 months, about 3 months, about 4 months, about 5 months, about 6 months, about 7 months, about 8 months, about 9 months, about 10 months, about 11 months, about 12 months or more; or by about 1 year, about 2 years, about 3 years, about 4 years, or by about 5 years or more.
  • stilbene and “stilbenoid” are interchangeable and refer to compounds based on the compound of formula (I):
  • formula (I) may be substituted at one or more suitable positions.
  • substituents include, but are not limited to, halogen, cyano, nitro, Ci-C 6 alkyl, Ci- C 6 haloalkyl, Ci-C 6 hydroxyalkyl, hydroxy, Ci-C 6 alkoxy, thiol, Ci-C 6 alkylthio, amino, Ci- C 6 alkyl amino, di- Ci-C 6 alkyl amino, carboxyl, Ci-C 6 alkoxycarbonyl, amido, methyl, and glycosyl.
  • stilbenes including resveratrol, and flavonoids are produced in plants and yeast through the phenylpropanoid pathway as illustrated by the reactions shown in Figure 1.
  • phenylpropanoid refers to compounds based on a 3- phenylprop-2-enoate backbone. Examples of such compounds include, but are not limited to, cinnamic acid, coumaric acid, caffeic acid, ferulic acid, 5-hydroxyferu!ic acid, sinapinic acid. cinnamoyi-CoA, p-coumaroyl-CoA, and the like.
  • phenylpropanoid derivative refers to any compound derived from, synthesized from, or biosynthesized from, a phenylpropanoid; i.e. a phenylpropanoid derivative includes any compound for which a phenylpropanoid compound is a precursor or intermediate.
  • phenylpropanoid derivatives include, but are not limited to, stilbenoid compounds and chalcone compounds.
  • Specific examples of phenylpropanoid derivatives include, but are not limited to, resveratroi, pinosylvin, pinocembrin chalcone, and pinocembrin.
  • dihydrophenylpropanoid refers to compounds based on a phenyipropanoate backbone. Examples of such compounds include, but are not limited to, dihydrocinnamic acid, phioretic acid, 3,4-dihydroxyhydrocinnamic acid, hydro ferulic acid, dihydrocoumaroyl-CoA, dihydrocinnamoyl-CoA, and the like.
  • dihydropinosy!vin dihydropinosylvincarboxylate, 3 -O-methyldihydropinosylvincarboxylate, 4-isoprenyl-3 -O- methy!dihydropinosylv incarboxylate (amorfrutin 1), 3-O-methyldmydropinosylvin, 4- isoprenyl-3-O-methyldihydropinosylvin (amorfrutin 2), 5-hydroxy-iunularic acid, and dihy droresveratrol .
  • phenylpropanoid pathway As used herein, the terms “phenylpropanoid pathway,” “phenylpropanoid derivative pathway,” “phenylpropanoid derivative synthesis pathway,” and “phenylpropanoid derivative biosynthesis pathway” are interchangeable and refer to any biosynthesis pathway in which a phenylpropanoid is a precursor or intermediate.
  • stilbene or a derivative thereof can be hydroxylated derivatives of stilbene and are thus encompassed by the term “stilbene” as used herein.
  • the term “stilbene” includes but is not limited to at least one of resveratrol, dihydroresveratrol, and pinosilvin; a glycosylated stilbene comprising piceid (3 -resveratrol monoglucoside or 5-resverarol monoglucoside), resveratroloside (4'-resveratrol monoglucoside), Mulberroside E (3,4'- resveratrol diglucoside), 3,5- resveratrol diglucoside, and 3,5,4'-resveratrol triglucoside and their dihydro- reduced equivalents; a methylated stilbene comprising pterostilbene (3,5- dimethoxy-4'-hydroxy-trans-stilbene), 3 ,5 ,4'-trimethoxystilbene, pinostilbene,
  • resveratrol refers to a compound seen in Figure 1 that may be synthesized, isolated, and purified from of a mixture of products produced in a host modified to express enzymes of the resveratrol biosynthetic pathway or that can be produced from naturally occurring sources, such as grapes.
  • Resveratrol further refers to derivatives and analogs thereof, including but not limited to forms of methylated and/or glucosylated resveratrol.
  • the resveratrol compound contemplated for use herein may be produced in vivo through expression of one or more enzymes involved in the resveratrol biosynthetic pathway in a recombinant yeast or in vitro using isolated, purified enzymes involved in the resveratrol biosynthetic pathway, such as those described in WO2006/089898, WO2008/009728, WO2009/016108, WO2009/124879, WO2009/124967, WO201 1/147818, WO2016/180956, and WO2016/189121 , which are incorporated by reference in their entirety. Therefore, resveratrol as defined herein can differ chemically from other sources of resveratrol, such as extracts from plants and derivatives thereof, or may include such plant extracts and derivatives thereof.
  • modified resveratrol can be used interchangeably to refer to a compound that can be derived from resveratrol or a compound with a similar structure to resveratrol.
  • modified resveratrol can refer to resveratrol-like molecules such as to glycosylated resveratrol molecules, methylated resveratrol molecules, or resveratrol molecules that are glycosylated and methylated.
  • glycosylation comprises covalently attaching one or a plurality of sugar or saccharide residues at one or more of the 3, 4', or 5 hydroxyl groups of resveratrol.
  • the saccharide moiety in each position can be independently zero, one, two, three, or multiple sugar residues, wherein all the sugar residues can be the same sugar residues or different sugar residues.
  • nootkatone refers to a compound seen in Figure 4 that may be synthesized, isolated, and purified from of a mixture of products produced in a host modified to express enzymes of the nootkatone biosynthetic pathway or that can be produced from naturally occurring sources, such as citrus plants. "Nootkatone” further refers to derivatives and analogs thereof.
  • the nootkatone compound contemplated for use herein may be produced in vivo through expression of one or more enzymes involved in the nootkatone biosynthetic pathway in a recombinant yeast or in vitro using isolated, purified enzymes involved in the nootkatone biosynthetic pathway, such as those described in U.S. Patent Application Publication Nos. 2015/0007368 and 2012/0246767. Therefore, nootkatone as defined herein can differ chemically from other sources of nootkatone, such as extracts from plants and derivatives thereof, or may include such plant extracts and derivatives thereof.
  • stilbene-containing compositions and methods of using the compositions that are effective at treating and preventing infections of phytopathogenic or facultative saprophytic microbes, and/or extending the shelf-life of a consumable product.
  • Some embodiments of the current disclosure aim to prevent or treat phytopathogenic or facultative saprophytic microbial infections, or to reduce the frequency or prevalence of phytopathogenic or facultative saprophytic microbial infections of consumable products, propagated plants, trees, flowers, fruit, propagated plant material or agricultural produce for use in seed, food or feed, thus extending the shelf-life of any consumable product.
  • fields, flower beds, greenhouses, or other locations with high concentrations of propagated plant material susceptible to infection by phytopathogenic or facultative saprophytic microbes be treated with stilbene-containing compositions so as to reduce the frequency of infection or severity of damage to a consumable product, propagated plants, and propagated plant material.
  • the current disclosure provides methods and uses for a composition comprising stilbene suitable for treating a surface, a consumable product, a propagated plant or propagated plant material, an environment rich in propagated plant material, or locations with high concentrations of propagated plants or propagated plant parts susceptible to damage by phytopathogenic or facultative saprophytic microbial infections, for delaying the onset of or reducing the frequency of phytopathogenic or facultative saprophytic microbial-induced damage to consumable products, propagated plants or propagated plant material.
  • some embodiments of the current disclosure are useful for increasing or retaining the commercial value or extending the shelf-life of a consumable product, a propagated plant or propagated plant material by applying a stilbene-containing composition to the consumable product, the propagated plant or propagated plant material to at least one of either prevent infection of the consumable product, the propagated plant or propagated plant material with a population of phytopathogenic or facultative saprophytic microbes, or treat such an infection resulting in maintained and/or improved propagated plant health and/or aesthetic appearance of the consumable product, or the propagated plant.
  • Additional aspects of the current disclosure are useful for reducing or preventing the occurrence of transmission of microbial diseases, or preventing contamination by microbial organisms, in meat or meat products, and/or extend the shelf-life of any meat or meat product.
  • the disclosure aims to prevent or treat phytopathogenic or facultative saprophytic microbial infections, or to reduce the frequency or prevalence of phytopathogenic or facultative saprophytic microbial infections of seeds. Damage to seeds caused by phytopathogenic microorganisms can occur as early as storage of the seeds or when the seeds are introduced into the soil, or during and immediately after germination of the seeds. This phase is critical since the roots and shoots of the growing plants are particularly sensitive and even minor damage can lead to deformation or to the death of the whole plant.
  • the compositions of the disclosure can be applied to the seed, medium to be planted with the seed or both through, for example, irrigation water.
  • Additional aspects of the current disclosure are intended to reduce or prevent the occurrence of transmission of phytopathogenic or facultative saprophytic microbial diseases by sap-sucking insects in a population of propagated plants treated with a nootkatone- containing composition and a stilbene-containing composition, either sequentially or simultaneously.
  • a sap-sucking pesticide i.e., nootkatone
  • an antimicrobial i.e., resveratrol
  • the simultaneous action of two or more compounds can provide a benefit greater than the sum of the individual components (i.e., synergy).
  • synergy when the combination interacts synergistically, a high level of disease control can be achieved with less than label rates of each individual component.
  • MOA modes of action
  • Such double-target combination treatments can be desirable in preventing the rapid spread of disease in areas of intensive plant propogation, as often used by, for example, modern farming techniques in which large areas are almost exclusively populated by a single variety of a single species of propagated plant.
  • stilbene such as resveratrol and derivatives thereof
  • resveratrol provides a sustainable and biodegradable alternative to current active agents against phytopathogenic or facultative saprophytic microbes.
  • a stilbene (i) may be present in a formulation or kit with at least one additional (ii) active ingredient, pesticide, insecticide, fungicide or bactericide.
  • Such compositions may be formulated for separate, simultaneous or successive administration.
  • (i) and (ii) may, for example, be provided as a kit.
  • the second active ingredient may be, for example any suitable class of phytopathogenic pesticides such as azoxystrobin, myclobutanil, propiconazole, thiophanate methyl, ziram, hypochlorites, chloramines, dichloroisocyanurate and trichloroisocyanurate, wet chlorine, chlorine dioxide, peroxides, peracetic acid, potassium persulfate, sodium perborate, sodium percarbonate, and urea perhydrate, iodine, concentrated alcohols (such as ethanol, 1-propanol, called also n-propanol and 2-propanol, isopropanol and mixtures thereof), phenolic substances, hexachlorophene, triclosan, trichlorophenol, tribromophenol, pentachlorophenol, cationic surfactants, benzalkonium chloride, cetyl trimethylammonium bromide or chloride, didecyldimethylammoni
  • compositions comprising stilbene (such as resveratrol) or a derivative thereof may be administered in a sprayable composition.
  • compositions comprising stilbene (such as resveratrol) or a derivative thereof may be administered within water applied to a consumable product, or propagated plants, such as in water used for irrigation or utilized in a predominantly aqueous growth media for the plant, such as in hydroponic growth.
  • compositions comprising stilbene (such as resveratrol) or a derivative thereof may be administered as a preventative treatment to prevent "colour break” or other damage to a consumable product, propagated plants or propagated plant material.
  • compositions comprising stilbene may be administered to a surface on or within a vehicle including but not limited to an agricultural vehicle, forestry vehicle, or vehicle for transporting consumable products, propagated plants, propagated plant produce, or agricultural or forestry equipment.
  • Surfaces to be treated for phytopathogenic or facultative saprophytic microbes can be any part of a consumable product, a propagated plant, propagated plant material, agricultural area, vehicles, or any agricultural, forestry, horticultural, food processing or food industry work surface, food handler, equipment, tools or storage containers.
  • Such surfaces may comprise plant stems, shoots, buds, leaves, flowers, fruit, wood, metal, plastic, gloves, sheets of wrapping plastic, cotton, wool, silk, satin, or any fabric suitable for use in agriculture, forestry, floristry, food processing, food transport or food storage.
  • stilbene compositions may be combined with existing technologies to treat and/or prevent phytopathogenic or facultative saprophytic microbial infections.
  • a fabric suitable for wrapping propagated plant material for transport or storage may be contacted, impregnated or coated with a composition comprising a stilbene.
  • An example of such a fabric is a thin transparent sheet or film (typically about 12 ⁇ to 8 ⁇ thick), herein referred to as a "plastic film", such as but not limited to plastic wrap or food wrap, such as SARAN® wrap.
  • Such sheets may be made from polyvinyl chloride, low density polyethylene, or polymers of glucose, including thin transparent sheets made from regenerated cellulose.
  • stilbene composition-coated or -impregnated films can be formed into bags, such as zippered bags for transporting, storing, displaying, portioning, or selling products. Further, stilbene composition-coated or -impregnated films can be combined with foam-based, cellulose-based, or any other packaging item that itself can be coated or impregnated with a stilbene containing composition to form single-use or reusable packaging containers in which perishable food can be transported, stored, displayed in a store, or sold. In addition, non-coated or impregnated packaging can be treated with a stilbene-containing composition to render the packaging resistant to pests and/or microbial diseases disclosed herein. In another embodiment, a stilbene-containing packet or other reservoir from which the stilbene can emanate can be inserted into a closed storage or packaging container to render the packaging resistant to pests and/or microbial diseases disclosed herein.
  • the active ingredients contemplated herein are used in the form of compositions.
  • the active ingredients can be applied to the consumable product to be treated either before, simultaneously or after the harvest.
  • the active ingredients can be applied, if desired, together with other carriers conventionally used in the art of formulation, surfactants or other additives which aid application.
  • Suitable carriers and additives can be solid or liquid and are the substances expediently used in the art of formulation, for example natural or regenerated mineral materials, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers.
  • Stilbene-containing compositions contemplated herein can be formulated for direct application to a surface, a consumable product, a propagated plant, propagated plant material, or an environment rich in propagated plant material to reduce the population or as a prophylactic to prevent the growth of the population or spread of the population to other locations of phytopathogenic, facultative saprophytic or saprotrophic microbes, by exposing the subject to the stilbene-containing composition.
  • stilbene-containing compositions contemplated herein can be formulated for application as a dip, such as by dispensing into or onto a zone or area of water in which the articles to be treated may be immersed.
  • a further manner of application includes coating/impregnating surfaces and/or articles with stilbene-containing compositions.
  • compositions contemplated herein can be in the form of an aqueous liquid, an oil-based liquid, a concentrated liquid, a gel, a foam, an emulsion, a slurry, a paint, a clear coat, a wax, a block, a pellet, a puck, a granule, a powder, a capsule, a vesicle, an effervescent tablet, slow release tablet, an impregnated dissolvable sheet or film, an impregnated material, and combinations thereof.
  • a composition may be formulated as a liquid or aerosol formulation suitable for application in a spray, a roll on, a dip, detergents, carpet cleaner, durable water repellence formulations.
  • a composition may be formulated for application by dispensing into or onto an area of water suitable for use as an immersion dip or volume of washing water into which articles to be treated and/or plants may be at least partially submerged.
  • the composition can be provided as an aerosol, a solution, an emulsion, an oil, a spray, a gel, a powder, a foam, a block, a pellet, a puck, a granule, a vesicle, a powder, a capsule, and combinations thereof.
  • a composition may be formulated comprising a portion of material such as a tissue, pad, cloth, sponge or sheet impregnated, immersed or coated with a liquid composition comprising stilbene at a concentration of between 0.0001 - 5% by volume of the liquid composition.
  • the material can be impregnated, immersed and/or coated with a liquid composition including stilbene at a concentration of between 0.0001 - 5% by volume of the liquid composition.
  • the portion of material is a disposable thin sheet of material such as a tissue, a wet wipe, or a wet pad, similar to those sold under the Swiffer®, Pledge®, Windex®, Clorox® brands.
  • compositions contemplated herein can contain a carrier and at least about 0.0001%, or at least about 0.001%, or at least about 0.01%), or at least about 0.1%>, or at least about 1%>, or at least about 2%>, or at least about 5%>, or at least about 7.5%>, or at least about 10%>, , or at least about 15%>, or at least about 20%>, or at least about 25%, or at least about 50%> by weight stilbene.
  • stilbene can be present in an amount that is greater than about 60%, about 70%, about 80%, about 90%), about 95%o or about 99%> by weight of the composition.
  • the provided compositions contain stilbene in an amount at or about 0.0001 % to at or about 2%, or about 0.001 %) to at or about 5%>, or about 0.01 % to at or about 75%> by weight of the composition.
  • a composition may contain stilbene in an amount of from at or about 1% to at or about 50% by weight of the composition.
  • a composition may contain stilbene in an amount of from at or about 5% to at or about 40% by weight of the composition.
  • a composition may contain stilbene in an amount of from at or about 10% to at or about 30% by weight of the composition.
  • a composition may contain stilbene in an amount of from at or about 15% to at or about 25% by weight of the composition.
  • a composition may contain stilbene in an amount of from at or about 1% to at or about 90% by weight of the composition. In another example, a composition may contain stilbene in an amount of about 10%, or about 15%, or about 20%), or about 25%>, or about 30%>, or about 50%> by weight of the composition. In another example, a composition may contain stilbene in an amount of up to about 99% or more by weight of the composition.
  • compositions contemplated herein can contain a carrier and at least about 1 ppm to about 1 ,000 ppm of the stilbene (one ppm is equivalent to 1 milligram of something per litre of water (mg/1) or 1 milligram of something per kilogram soil (mg/kg)).
  • the compositions comprise at least about 1 ppm, or at least about 10 ppm, or at least about 20 ppm, or at least about 25 ppm, or at least about 50 ppm, or at least about 62.5 ppm, or at least about 100 ppm, or at least about 125 ppm, or at least about 150 ppm, or at least about 200 ppm, or at least about 250 ppm, or at least about 500 ppm, or at least about 1 ,000 ppm, or at least about 5,000 ppm of the stilbene.
  • the stilbene can be present in an amount that is about 10 ppm to about 25 ppm, or about 25 ppm to about 50 ppm, or about 50 ppm to about 62.5 ppm, or about 62.5 ppm to about 100 ppm, or about 100 ppm to about 125 ppm, or about 125 ppm to about 150 ppm, or about 150 ppm to about 200 ppm, or about 200 ppm to about 250 ppm, or about 250 ppm to about 500 ppm, or about 500 ppm to about 1 ,000 ppm, or about 1 ,000 ppm to about 5,000 ppm.
  • compositions contemplated herein can contain a carrier, a stilbene and further comprise at least about 1 ppm to about 1 ,000 ppm of nootkatone (one ppm is equivalent to 1 milligram of something per liter of water (mg/1) or 1 milligram of something per kilogram soil (mg/kg)).
  • the compositions comprise at least about 1 ppm, or at least about 10 ppm, or at least about 20 ppm, or at least about 25 ppm, or at least about 50 ppm, or at least about 62.5 ppm, or at least about 100 ppm, or at least about 125 ppm, or at least about 150 ppm, or at least about 200 ppm, or at least about 250 ppm, or at least about 500 ppm, or at least about 1 ,000 ppm, or at least about 5,000 ppm of nootkatone.
  • nootkatone can be present in an amount that is greater than about 10 ppm, or about 25 ppm, or about 50 ppm, or about 62.5 ppm, or about 100 ppm, or about 125 ppm, or about 150 ppm, or about 200 ppm, or about 250 ppm, or about 500 ppm, or about 1 ,000 ppm, or about 5,000 ppm of the composition.
  • nootkatone can be present in an amount that is about 10 ppm to about 25 ppm, or about 25 ppm to about 50 ppm, or about 50 ppm to about 62.5 ppm, or about 62.5 ppm to about 100 ppm, or about 100 ppm to about 125 ppm, or about 125 ppm to about 150 ppm, or about 150 ppm to about 200 ppm, or about 200 ppm to about 250 ppm, or about 250 ppm to about 500 ppm, or about 500 ppm to about 1,000 ppm, or about 1,000 ppm to about 5,000 ppm.
  • a contemplated stilbene-containing composition is provided as a concentrate.
  • a stilbene-containing composition may be provided as a 20X, or a 10X, or a 5X, or a 3X concentrate that can be diluted by an end user with an appropriate solvent to achieve a IX working concentration.
  • a stilbene- containing composition may be provided to an end user at a IX working concentration.
  • any concentration is contemplated for use herein.
  • compositions provided as concentrates can be used without dilution at all or may be diluted from a highly concentrated concentrate (e.g., about 20X to about 100X) to some multiple of concentration higher than IX, such as 2X, 2.5X, 3X, etc.
  • dilute concentration such as 1/2X, 1/4X, 1/lOX, etc. While concentrates are more preferred as commercially available goods, the industry and end consumers typically apply dilute compositions to a consumable product, or propagated plants, propagated plant material, materials and surfaces.
  • a contemplated composition may be seen in Table 1, where ingredients can be measured in percent volume per volume, percent weight per volume, or percent by weight.
  • compositions contemplated herein may include stilbene and one or more additional active ingredients.
  • the one or more additional active ingredients may be effective against at least one of pests of consumable products, propagated plants, phytopathogenic microbes, facultative saprophytic microbes, and/or saprophytic microbes.
  • the one or more additional active ingredient may have toxicity for insects, or bacteria or fungi.
  • the additional active ingredients may be a bactericide, bacteristatic, fungicide, fungistatic, microbicide, microbistatic, pesticide, herbicide, insecticide, and larvicide.
  • the additional active ingredients may have highly selective toxicity for a specific sap-sucking insect, such as aphids or thrips.
  • an additional active ingredient can be lipid-soluble so that it can be released over an extended period of time, such as, for example, approximately 2 months.
  • additional active ingredients include plant essential oil compounds or derivatives thereof.
  • examples include aldehyde C16 (pure), a-terpineol, amyl cinnamic aldehyde, amyl salicylate, anisic aldehyde, benzyl alcohol, benzyl acetate, cinnamaldehyde, cinnamic alcohol, carvacrol, carveol, citral, citronellal, citronellol, p- cymene, diethyl phthalate, dimethyl salicylate, dipropylene glycol, eucalyptol (cineole) eugenol, is-eugenol, galaxolide, geraniol, guaiacol, ionone, menthol, methyl salicylate, methyl anthranilate, methyl ionone, methyl salicylate, nootkatone, a-pheliandrene
  • a contemplated composition may include a stilbene to additional active ingredient ratio of about 1 : 10, or about 1 :8, or about 1 :6, or about 1 :4, or about 1 :2, or about 1 : 1 , or about 2: 1 , or about 4: 1 , or about 6: 1 , or about 8: 1 , or about 10: 1.
  • compositions contemplated herein can include a stilbene in combination with one or more additives, such as a fragrance, a preservative, a propellant, a pH buffering agent, a UV blocker, a pigment, a dye, a surfactant, an emulsifier, a solvent, a salt, an acid, a base, an emollient, a sugar, and combinations thereof.
  • additives include disinfectants, such as quaternary ammonium compounds, phenol-based antimicrobial agents, and botanical oils with disinfectant properties.
  • stilbene-containing compositions can include a carrier, such as an aqueous liquid carrier, water, a saline, a gel, an inert powder, a zeolite, a cellulosic material, a microcapsule, an alcohol such as ethanol, a hydrocarbon, a polymer, a wax, a fat, an oil, and the like.
  • a carrier such as an aqueous liquid carrier, water, a saline, a gel, an inert powder, a zeolite, a cellulosic material, a microcapsule, an alcohol such as ethanol, a hydrocarbon, a polymer, a wax, a fat, an oil, and the like.
  • carriers include agrotextiles and plastic film or food wrap.
  • Some carriers include time release materials where a stilbene-containing composition may be released over a period of hours, or days, or weeks.
  • Additional carriers include agricultural substances, such as, a natural fertilizer, a chemical fertilizer, mulch, compost, top soil, potting soil, vermiculite or other soil amendments, or agricultural waste products, and mixtures thereof.
  • Solid carriers which are used for example for dusts and dispersible powders are typically comprised of ground natural minerals, such as calcite, talc, kaolin, montmorillonite or attapulgite. To improve the physical properties, it is also possible to add highly-disperse silica or highly-disperse absorptive polymers.
  • Suitable paniculate adsorptive carriers for granules are porous types, for example pumice, brick grit, sepiolite or bentonite, and suitable non-sorptive carrier materials are, for example, calcite or sand.
  • suitable non-sorptive carrier materials are, for example, calcite or sand.
  • pregranulated materials of inorganic or organic nature can be used, such as, in particular, dolomite or comminuted plant residues.
  • Carriers may be added to a composition in an amount of about 10%, or about 15%, or about 20%, or about 25%, or about 30%, or about 50% by weight of the composition.
  • a carrier can be present in an amount that is at or greater than about 60%, about 70%, about 80%, about 90%, about 95%, or about 99% by weight of the composition.
  • Solvents suitable for incorporation into compositions according to some aspects of the current invention include but are not limited to aromatic hydrocarbons, preferably the fractions Cs to C 12 , for example xylene mixtures or substituted naphthalenes, phthalic esters, such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons, such as cyclohexane or paraffins, alcohols and glycols and also their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones, such as cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, and free or epoxidized vegetable oils, such as epoxidized coconut oil or soya oil; water or solvents derived from natural products.
  • aromatic hydrocarbons preferably the fractions Cs to C 12 ,
  • suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties.
  • surfactants are also to be understood as meaning mixtures of surfactants.
  • Additives which aid application of compositions according to some aspects of the invention include natural or synthetic phospholipids from the series of the cephalins and lecithins, for example phosphatidylethanolamine, phosphatidylserine, phosphatidylglycerine, or ly so lecithin.
  • the active ingredient is mixed thoroughly with the additives and the mixture is ground thoroughly in a suitable mill. This gives wettable powders which can be diluted with water to give suspensions of any desired concentration.
  • Emulsions of any desired dilution which can be employed in crop protection can be prepared from this concentrate by dilution with water.
  • Ready-to-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry seed treatment.
  • the active ingredient is mixed with the additives, ground and moistened with water. This mixture is extruded and subsequently dried in a stream of air.
  • the finely ground active ingredient is applied uniformly to the kaolin which has been moistened with polyethylene glycol. This gives dust-free coated granules.
  • suspension concentrate from which suspensions of any desired dilution can be prepared by dilution with water.
  • dilutions can be used for treating live plants and plant propagation material by means of spraying, pouring-on or immersion and for protecting them against microbial infection.
  • compositions comprising active ingredients may be applied once per day, once per week, twice per week, once per two weeks, once per month, once per two months, once per three months, or once per lifecycle of the object to which the composition is being applied.
  • Compositions according to aspects of the current invention may be employed as pure active ingredients or, preferably, together with the auxiliaries conventionally used in the art of formulation and are therefore processed in a known manner to give, for example, emulsion concentrates, spreadable pastes, ready-to-spray or ready-to-dilute solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, or encapsulations, for example in polymeric materials.
  • the methods of application such as spraying, atomizing, dusting, scattering, brushing on, submerging, dipping, coating, pouring or rubbing, and the type of composition are selected to suit the intended aims and prevailing circumstances.
  • a preferred method of applying a mixture of active ingredients comprising in each case at least one of the active ingredients and its application to the aerial parts of the plant, especially the foliage (foliar application). Number and rates of application depend on the biological and climatic environment of the pathogen.
  • the active compounds can also be applied to seed kernels, grains, fruits or harvested crops for the purposes of coating, either by soaking the roots, seed kernels, grains, fruits or harvested crops in succession with a liquid preparation of an active ingredient or by coating them with a moist or dry preparation which already comprises the active ingredients.
  • other types of application to plants are possible in specific cases, for example the targeted treatment of buds or fruit-bearing parts of the plant.
  • a consumable product, or a propagated plant material or propagated plants can be treated prior to harvest, concomitant with harvest, prior to transportation or during a period of quarantine.
  • a consumable product, or a propagated plant material or propagated plants can be treated in combination with a biocide, for example, when plant breeding to produce resistant varieties.
  • a consumable product, or a propagated plant material or propagated plants can be treated during a period of high humidity (e.g., about 70% or higher) and/or high temperature (e.g., about 20°C or higher).
  • high humidity e.g., about 70% or higher
  • high temperature e.g., about 20°C or higher
  • a consumable product, or a propagated plant material or propagated plants can be treated prior to harvest and then subjected to at least one subsequent treatment after harvest, prior to transportation or during a period of quarantine or storage.
  • treatment extends the shelf-life of the consumable product.
  • the subsequent treatment may be the same as the first, or may comprise a different treatment including but not restricted to any of refrigerating, freezing, heating to 30°C or higher, treatment with red light, treatment with ultra-violet light, treatment with a soap spray, applying a composition including, for example, organochlorides, organophosphates, carbamates, pyrethroids, neonicotinoids, ryanoids (such as DDT, methoxychlor, diazinon, oxamyl, carbofuran, methomyl, dinotefuran, cyfluthrin, tetramethrin, acetamiprid, thiamethoxam, chlorantraniliprole or flubendiamide), and combinations thereof.
  • a composition including, for example, organochlorides, organophosphates, carbamates, pyrethroids, neonicotinoids, ryanoids (such as DDT, methoxychlor, diazinon, ox
  • an agricultural area or environment rich in propagated plant material is treated with a composition comprising nootkatone or a derivative thereof, and is then subjected to a subsequent treatment with a composition comprising a stilbenoid (such as resveratrol) or a derivative thereof.
  • a composition comprising nootkatone or a derivative thereof, and is then subjected to a subsequent treatment with a composition comprising a stilbenoid (such as resveratrol) or a derivative thereof.
  • compositions comprising active ingredients are typically 1 g to 1 kg of a.i./ha, in particular 10 g to 100 g of a.i./ha, particularly preferably 15 g to 70 g of a.i./ha per application.
  • the rates of application are typically 0.0001 g - 100 g of a.i./Liter of solution, 0.001 g - 75 g of a.i./Liter of solution, 0.01 g - 50 g of a.i./Liter of solution, 0.1 g - 25 g of a.i./Liter of solution, 1.0 g - 10 g of a.i./Liter of solution, preferably 0.01 g - 1.0 g of a.i./Liter of solution, or 0.1 g - 10 g of a.i./Liter of solution or 0.0001 g - 100 g of a.i.
  • contemplated methods include treating agricultural or forestry areas, greenhouses or other artificial microclimates such as within human dwellings or under sheets of agrotextiles.
  • treatment with a composition including a stilbene may be performed at a temperature between 0 and 25 C, preferably between 5 C and 20 C.
  • treatment with a composition comprising a stilbene may be performed prior to the growing season, or in the first two months of the growing season, or once the minimum overnight temperature exceeds at least 7 C, preferably at least IO C.
  • Various methods according to some aspects of the current invention may be employed to contact a consumable product, or propagated plants, propagated plant material, surfaces, areas rich in propagated plant parts, agricultural areas susceptible to infection by phytopathogenic, facultative saprophytic or saprotrophic microbes with stilbene-containing compositions.
  • Such methods may include addition of resveratrol and stilbene-containing compositions to water in which the propagated plant material, surface or area to be treated may be rubbed, wiped, brushed, dipped or sprayed.
  • a stilbene can be applied, such as by directly pouring the composition into the water or placing a composition dispenser within a sink, rain collection receptacle, tank, irrigation channel, hand pump spray or any other appropriately sized receptacle such that the surface, plant, portion of a plant, object or environment to be treated comes into contact with the stilbene at an effective concentration of, for example, between 1 and 5,000 ppm.
  • the consumable product, or plant, portion of a plant, surface, object or environment to be treated may be exposed to any of the contemplated stilbene-including compositions for about 1 second to about 24 hours before rinsing or treatment with uv light, or the applied resveratrol and stilbene-containing composition may be left without active removal to degrade naturally.
  • the consumable product, or plant, portion of a plant, surface, object or environment to be treated is exposed to an effective amount of stilbene, such as, at concentration of 250 ppm, for 60 seconds.
  • methods of application to a subject, surface, a consumable product, or plant material of an effective concentration of a stilbene by liquid, spray, powder, or wash is preferably performed in a commercial or domestic area for growing plants such as an agricultural field, forest, flowerbed, a polytunnel, greenhouse, conservatory, office, home, and/or dwelling.
  • dispensers or applicators for dispensing or applying a composition contemplated herein are intended to be reused.
  • the dispenser or applicator upon dispensing a stilbene-containing composition, the dispenser or applicator can be refilled.
  • a dispenser or applicator is a single-use device or substance that functions as a stilbene composition carrier that is itself dispensed or degraded.
  • a dispenser or applicator i.e., carrier
  • Topical compositions disclosed herein may be dispensed using a dispenser or applicator including one or more of a spray bottle, a brush, a dropper, a sponge, a soft-tipped marking device with reservoir, pressurized dispenser, an aerosol can, a roll on bottle, a wipe, a tissue, a duster, and other devices suitable for application to surfaces, objects, propagated plants or areas rich in propagated plant material.
  • consumable products, propagated plants, propagated plant material, surfaces, areas rich in propagated plant parts, agricultural areas susceptible to infection by phytopathogenic, facultative saprophytic or saprotrophic microbes with stilbene-containing compositions may be sprayed, brushed, wiped, dipped, and/or soaked with a stilbene-containing composition.
  • compositions contemplated herein may be applied to one or more surfaces using an applicator having a reservoir for carrying a composition in a wet form and/or a dry form.
  • applicators that may be used include an aerosol container with a spray nozzle with or without a spray straw to focus delivery of the composition, a spray gun, an impregnated sheet, film, and/or matrix where the composition is released onto the surface by a releasing agent, such as water or other carrier.
  • a pump sprayer a trigger sprayer, a pressurized spraying device, a sponge, a squeegee, an airbrush, a brush, or a roller.
  • composition may alternatively be applied by spraying or dispersing over at least a portion of an agricultural area susceptible to infection phytopathogenic, facultative saprophytic or saprotrophic microbes, including but not limited to spraying from a tractor, irrigation spray, helicopter, or crop duster or airplane.
  • Another aspect of the current invention includes pretreatment of surfaces, objects, consumable products, propagated plants, propagated plant material, surfaces, areas rich in propagated plant parts, agricultural areas susceptible to infection by phytopathogenic, facultative saprophytic or saprotrophic microbes with stilbene-containing compositions to prevent said microbes from spreading and/or increasing in population size.
  • This may be accomplished by coating the surfaces or objects with compositions that resist removal from the surface and contain an amount of a stilbene, such as a paint, a clear coat, a wax, an oil, an adhesive, a resin, a cleaning solution, and combinations thereof.
  • Another approach includes lining the surfaces, objects, or areas rich in propagated plant material, with one or more stilbene-impregnated materials, such as thermoplastic or thermoset sheets, plastic wrap, paperboard, or cardboard impregnated with nootkatone.
  • a nootkatone- impregnated agrotextile may be used to at least partially enclose a plant growing area (including but not limited to a greenhouse or flower bed) or a transport container or receptacle, including boxes, bins, cartons, etc., or storage area for plants or portions of plants, such as barns, elevators, etc.
  • a propagated plant part or propagated plant material is pretreated by at least partially enclosing in a plastic container, plastic wrap or plastic film impregnated, coated or contacted with a stilbene-containing composition so as to reduce the susceptibility to infection by phytopathogenic, facultative saprophytic or saprotrophic microbes.
  • the plastic container, plastic wrap or plastic film or may be at least partially air and/or water permeable.
  • the plastic container, plastic wrap or plastic film may be a bioplastic or biodegradable plastic, preferably also comprising a biodegradable plasticizing agent.
  • the pretreatment or preventative composition comprising a biodegradable plastic, biodegradable plasticizer and a nature-identical stilbene (indistinguishable from a stilbene found in nature) is preferred in aspects of the invention relating to methods of farming, transportation and storage of propagated plants and/or propagated plant materials with the highest sustainability and minimal environmental impact of waste materials.
  • the dispenser when the dispenser is a disposable thin sheet of material such as a tissue, a wet wipe, or a wet pad, such dispensers may be used to treat individual consumable products, propagated plant parts or propagated plant materials by physically removing at least a portion of a population of phytopathogenic, facultative saprophytic or saprotrophic microbes, for example, by wiping.
  • a protective residue, layer, or film of stilbene-containing composition is deposited on the treated surface to prevent reinfection. In this way, treatment may be two-fold: physical removal and chemical disinfection and/or inhibition.
  • Such sheets of material may be prepackaged for use such as in resealable, liquid-impervious pouches.
  • a further treatment approach is to construct surfaces, objects, or storage or transport receptacles with stilbene-impregnated or stilbene-coated materials, such as plastics, wood, cloth, textiles, composites, or porous materials to prevent re-infection of propagated plants, propagated plant parts and agricultural equipment between harvests, plantings, or other suitable interval.
  • stilbene-impregnated or stilbene-coated materials such as plastics, wood, cloth, textiles, composites, or porous materials to prevent re-infection of propagated plants, propagated plant parts and agricultural equipment between harvests, plantings, or other suitable interval.
  • Such an approach is particularly suitable for construction of furniture, greenhouses, agrotextiles, gloves, crates, boxes, vases, pots or bags suitable for growing, transporting, handling, or displaying of propagated plants or propagated plant materials.
  • the approaches disclosed herein can be used alone or in any combination.
  • An antimicrobial effect is present if the action of the active ingredients show a significantly lower disease incidence, disease severity, or index of infection than the untreated surface or subject to be treated.
  • Colletotrichum gloeosporioides Colletotrichum gloeosporioides, Fusarium sp. Alternaria alternata apple pathotype mali (A. mali), Botrytis cinerea, Rhizopus sp, Mucor sp, Penicillium expansum, P. Digitatum, Monilinia laxa and Trichothecium roseum were all isolated from infected fruits.
  • mali - isolated from infected apple leaf, second isolate from infected apple; Botrytis cinerea - isolated from infected strawberry fruits; Trichothecium roseum - isolated from infected apple fruit. Monilinia laxa was isolated from infected sweet cherries. Rhizopus sp was isolated from mango. Mucor sp was isolated from tomato. Penicillium expansum and P. digitatum were isolated from infected oranges.
  • Example 1 Inhibition oi Alternaria sp. growth and spore generation by resveratrol.
  • Alternaria species can cause rot of fruits ⁇ e.g. pomes, apples, pears, mangoes, and stone fruits) and vegetables ⁇ e.g. curbits, tomato, eggplant, peppers, and brassica), and are the most common pathogen present in rotten apples ⁇ see FIG.6). Alternaria species can cause decay to most fresh fruit and vegetables pre- or post-harvest, and have become a significant disease for fresh fruit, causing an estimated yield loss of about 30% to about 60%. Additionally, Alternaria can produce many toxins ⁇ e.g. alternariol, altertoxins I, II, and III, tenuazonic acid), and these toxins can occur in juices and down-stream food and beverage products of infected crops ⁇ e.g. apple juice, cranberry juice, grape juice, prune nectar, raspberry juice, red wine, and lentils).
  • Pathogenic Alternaria was isolated from an infected apple leaf showing symptoms of blotch. Agar plates containing media and various concentrations of resveratrol were made and inoculated with Alternaria. After both 5 and 10 days of incubation, the results demonstrated that Alternaria mycelial growth was inhibited in plates containing resveratrol. Figure 5 demonstrates that resveratrol inhibited growth of Alternaria sp by 50% after ten days of incubation (see also Table 2).
  • the EC50 for resveratrol was determined to be 250 ppm (250 ⁇ / ⁇ 1), and the EC50 for resveratrol when combined with 120 ppm of nootkatone was determined to be 120 ppm (120 ⁇ / ⁇ 1).
  • Alternaria alternata isolated from infected sweet cherries displayed mycelial growth with a green color at both sides of a Potato Dextrose Agar (PDA) plate. After 24 hours of treatment, no conidia germination of Alternaria alternata was observed by treatment with 125 ppm and 250 ppm of resveratrol, but small germ tubes were observed with treatment of 62.5 ppm of resveratrol alone, or with 62.5 ppm of nootkatone alone. Surprisingly, the combination of nootkatone at 62.5 ppm (NKT) and resveratrol at 62.5 ppm (RESV) resulted in no conidia germination. Comparatively, carbendazin, a commercially available fungicide, was used as a control (at 10 ppm), and A. alternata condidial germination was observed ⁇ see FIG.10).
  • Example 2 Inhibition of Botryodiplodia theobromae growth by combination of resveratrol and nootkatone.
  • Botryodiplodia theobromae also referred to as Lasiodiplodia theobromae, causes damage at both pre- and post-harvest stages and affects more than 200 plant species.
  • Post-harvest diseases include stem end rot, fruit and tuber rots, which affect crops including mangoes, oranges, avocados, papayas, bananas, cocoa, and yams.
  • B. theobromae causes dieback, blights, and root rot in many plants and severely affects guava, coconut, and grapes.
  • B. theobromae was isolated from infected oranges and brought to pure culture by repeated sub-culturing by fungal tip isolation method. Conidia germination of B. theobromae was inhibited by 24 hours of treatment with the combination of resveratrol (RESV) and nootkatone (NKT), each at 250 ppm (tested by poisoned food plate method on PDA). Resveratrol alone at 250 ppm or nootkatone alone at 250 ppm did not effectively inhibit conidia germination. Comparatively, tebuconazole, a commercially available fungicide did not inhibit conidia germination at 10 ppm (see FIG. l 1).
  • Example 3 Inhibition of Botrytis cinerea growth by resveratrol.
  • Botrytis cinerea is a high-risk pathogen that can cause rot of fruits ⁇ e.g. strawberry, apples, pears, mangoes, and stone fruits) and vegetables ⁇ e.g. tomato, eggplant, peppers, legumes, brassica species, roses, gerbera, lisianthus and dendrobium species), and is quick to develop resistance against many fungicides.
  • Pathogenic B. cinerea was isolated from infected strawberry fruits showing symptoms of infection (the B. cinerea strain tested contained a mutation at amino acid 198 (Glu to Ala), which is known to cause resistance to Carbendazim).
  • Agar plates containing media and various concentrations of resveratrol (10-250 ppm) were made and innoculated with B. cinerea. After seven days of incubation, the results demonstrated that B. cinerea mycelial growth was inhibited in plates containing resveratrol.
  • Figure 12 demonstrates that resveratrol inhibited growth of B. cinerea by 74% after seven days of incubation ⁇ see also Table 3).
  • the EC 50 for resveratrol was determined to be 132 ppm (132 ⁇ g/ml).
  • ketoconazole - 10 ppm 24.28 0.14
  • Pathogenic B. cinerea was isolated from infected strawberry fruits showing symptoms of infection (the B. cinerea strain tested contained a mutation at amino acid 198 (Glu to Ala), which is known to cause resistance to Carbendazim).
  • Agar plates containing media and various concentrations of resveratrol (250 - 500 ppm) were made and inoculated with B. cinerea. After seven days of incubation, the results demonstrated that B. cinerea mycelial growth was inhibited in plates containing resveratrol.
  • Figure 12 demonstrates that resveratrol inhibited growth of B. cinerea by 87% after seven days of incubation ⁇ see also Table 4).
  • Pathogenic B. cinerea was isolated from infected strawberry fruits showing symptoms of infection (the B. cinerea strain tested contained a mutation at amino acid 198 (Glu to Ala), which is known to cause resistance to Carbendazim).
  • Agar plates containing media and various concentrations (mixed at a 1 : 1 ratio of resveratrol to nootkatone) of resveratrol (10 - 155 ppm) in combination with nootkatone (10 - 155 ppm) were made and inoculated with B. cinerea. After five days of incubation, the results demonstrated that B. cinerea mycelial growth was inhibited in plates containing the combination of resveratrol and nootkatone.
  • Figure 14 and Figure 15 demonstrate that the combination of resveratrol and nootkatone inhibited growth of B. cinerea by 90% after five days of incubation (see also Table 5 and Table 6).
  • the EC50 for the combination of resveratrol and nootkatone was determined to be 32 ppm (32 ⁇ / ⁇ 1; at a 1 :1 ratio, 32 ppm resveratrol and 32 ppm nootkatone).
  • Example 4 Inhibition of spore germination and mycelial growth of Botrytis cinerea by resveratrol and nootkatone.
  • Strawberry fruit was purchased off the shelf of an air-conditioned store and left on a table for two days for disease to progress.
  • the B. cinerea strawberry isolate was carbendazim resistant (due to a mutation at 198 AA from GAG (Glu) to GCG (Ala) in the tubulin beta chain).
  • Mycelial growth (growth rate in centimeters per day) of B. cinerea was measured for the first five days, and then from days five to ten. Treatment with the combination of nootkatone and resveratrol, each at 60 ppm, resulted in a reduction of mycelial growth rate from 0.3 cm/day on the 5 th day down to 0.07 cm/day on the 10 th day.
  • the growth-rate resulting from treatment with nootkatone alone at 60 ppm, or with resveratrol alone at 60 ppm was about 10-fold and 5-fold more, respectively, than the growth-rate resulting from treatment with the combination of nootkatone and resveratrol, each at 60 ppm, on the 10 th day ⁇ see FIG.18A and 18B).
  • Example 5 Inhibition of Colletotrichum gloeosporoides growth by resveratrol.
  • Example 6 Inhibition of Fusarium oxysporum growth by resveratrol.
  • Fusarium oxysporum is a pathogen that can cause rot of fruits (e.g. banana and pineapple) and vegetables (e.g. curbits, tomato, eggplant, peppers, asparagus, potatoes, corn, onions, and garlic). Additionally, F. oxysporum can produce many toxins (e.g. mycotoxins, fumonisin, zearalenone, and aflatoxin Bl), and these toxins are known carcinogenic metabolites.
  • fruits e.g. banana and pineapple
  • vegetables e.g. curbits, tomato, eggplant, peppers, asparagus, potatoes, corn, onions, and garlic.
  • F. oxysporum can produce many toxins (e.g. mycotoxins, fumonisin, zearalenone, and aflatoxin Bl), and these toxins are known carcinogenic metabolites.
  • Resveratrol also prevented spore germination in F. oxysporum. Resveratrol prevented spore germination (about 20% inhibition at 250 ppm), while healthy spores germinated in 98% of control samples after 16 hours.
  • Example 7 Inhibition of Trichothecium roseum growth and spore germination by resveratrol.
  • Trichothecium roseum is an emerging pathogen that can cause rot of fruits ⁇ e.g. grapes, oranges, apples, bananas, nectarines, peaches, and plums) and vegetables ⁇ e.g., tomato, corn, muskmelon, and watermelon). Additionally, T. roseum can produce many toxins ⁇ e.g. mycotoxins, trichothecenes, neosolaniol), and these toxins are known cytogenic metabolites that are slow to degrade.
  • Agar plates containing media and various concentrations of resveratrol (10-250 ppm) were made and innoculated with T. roseum (apple isolate). After ten days of incubation, the results demonstrated that T. roseum mycelial growth was inhibited in plates containing resveratrol.
  • Figure 23 demonstrates that resveratrol inhibited growth of T. roseum by more than 55% after ten days of incubation ⁇ see also Table 9).
  • the EC 50 for resveratrol was determined to be 88 ppm (88 ⁇ ).
  • Resveratrol also prevented spore germination in T. roseum. Resveratrol completely prevented spore germination at 125 ppm, while healthy spores germinated in 98% of control samples after 18 hours. Conidia (asexual spores) of T. roseum are heavily damaged by 62.5ppm of resveratrol ⁇ see Figure 24). Less than 1% of spores germinated, and with much shorter germ tubes compared to control. Malformation of spores was observed and there was no spore germination at 125 ppm of resveratrol, and only 20-30% spores germinated in 31.25 ppm of resveratrol.
  • Example 8 Inhibition of Monilinia laxa growth by resveratrol on harvested fruit.
  • M. laxa primarily infects apples, pears, plums, peaches, and cherries, and is commonly observed in cherries in Europe ⁇ see FIG.25).
  • M. fructicola by contrast, is a common cherry pathogen in the U.S. but not in Europe.
  • M. laxa was isolated from cherry fruit purchased off the shelf in an air-conditioned store and left on table for 2 days to allow the infection to progress.
  • Example 9 Inhibition of Colletotrichum gloeosporoides growth by resveratrol on harvested fruit.
  • Apples (variety Red Delicious) were procured from a local orchard. The apples did not have pesticide applications within the last 50 days and did not have a wax coating. Colletotrichum gloeosporoides was isolated from naturally infected mango fruits, and spores of C. gloeosporioides were harvested from PDA plate of a 10-15 days old culture. The fruit body of the cultures (acervuli) were picked and immersed in water for 15 minutes to get the mucilage dissolved. Spores were separated by filtering spore suspension through sterile cheese cloth to remove mycelial bits. Spore suspension of 10- 13x10 4 spores was prepared by counting in Hemocytometer. Infection was carried out by spraying spores on apples.
  • Apples were soaked for one minute in the solutions containing resveratrol or carbendazim, while control apples were either treated with water alone (after infected) or 2% ethanol in water (apple not infected).
  • apples were sprayed with C. gloeosporioides spores 48 hours after being dipped in treatment (resveratrol, carbendazim or control).
  • apples were sprayed with C. gloeosporioides spores and left for 48 hours (allowing spores to adhere and germinate) before being dipped in treatment (resveratrol, carbendazim or control).
  • Apples were then incubated at 95% humidity and 23°C on sterile filter paper in plastic trays and covered with aluminum foil. As shown in Figure 27, and Tables 10 and 11, resveratrol was able to both prevent and cure C. gloeosporioides infection in apples. Surprisingly, 250 ppm resveratrol was better than 500 ppm of the commercial fungicide carbendazim at preventing C. gloeosporioides infection.
  • Example 10 Preservation of cherries following treatment with compositions comprising resveratrol and/or nootkatone.
  • fungicides Efforts to reduce fruit loss have used a variety of fungicides to little effect. For example, iprodione was used extensively as a postharvest treatment of sweet cherries until March 1996. The manufacturer restricted applications to no fewer than 7 days before harvest. For post-harvest applications, captan and tebuconazole are used in the United States. However, captan is seldom used because residues on fruit are prohibited in several export markets. Tebuconazole, on the other hand, is considered a medium risk fungicide, but resistance to this fungicide develops quickly. For example, Monilinia spp. resistance to tebuconazole have been reported.
  • An essential oil (thyme oil diluted to 100 ⁇ /L in ethanol) was used as a second positive control representing a nature-derived alternative.
  • a negative control was also employed, consisting of the ethanol solution used to make the resveratrol and nootkatone stock solutions for this series of experiments.
  • Thyme oil (100 ⁇ /L) 5 77.27%
  • Amistar TOP® (500 ⁇ /L) 3 86.36%
  • the test results indicate a dosage-dependent antifungal effect following treatment of fruits with compositions comprising resveratrol.
  • the anti-spoilage effect of resveratrol was further enhanced by co-treatment with nootkatone, and it was further noted that fruits treated with a blend of resveratrol and nootkatone had a fresh appearance indicated by a tighter and shinier skin. Based on these results, it is believed that above 90% of cherries can be protected from spoilage with a pre-harvest treatment or an immediate post-harvest treatment of compositions comprising resveratrol, with or without nootkatone, leading to an extended shelf life.
  • Example 12 Preservation of meat by resveratrol.
  • Mutton was dipped in resveratrol for one minute and monitored for changes in texture and color.
  • Resveratrol preserved color in the meat for 12 hours when left at room temperature and for 24 hours when refrigerated. Twelve hours after treatment with resveratrol, the tensile strength of the meat was weak when pulled. Good texture retention was demonstrated in meat treated with 500 ppm of resveratrol, surprisingly, texture of meat treated with 500 ppm of resveratrol was not detectably different at 12 hours compared to at zero hours. Texture of meat treated with 125 ppm or 250 ppm resveratrol demonstrated a slight reduction in texture and was similar to the texture of meat treated with sodium nitrite.
  • Figure 31 and Figure 32 demonstrate preservation of texture and color of meat treated with resveratrol.
  • Example 13 Susceptibility of Uncinula necator to treatment with resveratrol.
  • Treatment Stock solutions of resveratrol were prepared by dissolving 50mg of resveratrol in 1ml of ethanol. Stock solutions of sulphur were prepared at 2mg/ml. A resveratrol test formulation was prepared at 10% active ingredient concentration and dissolved in milli Q water to get 50mg/ml. Sulphur was used as a positive control and prepared from Sultaf 80 WG diluted in milli Q, just before use. The final test concentrations for resveratrol were 500, 250, 125 and 62.5 ppm, and sulphur was 2000 ppm.
  • the spore germination assay was performed using a 96 well micro titre plate in a sterile environment. One hundred microliters of spore suspension were added to each well, followed by a test concentration of either resveratrol or sulphur. For negative controls, water alone was added and for solvent control, instead of test compounds, 5 ⁇ 1/ ⁇ 1 ethanol was added to the media. Compound control and media control without spores were also maintained. For each treatment, triplicate wells were maintained with about 1000 spores in each well. Plates were incubated at 25°C in a moist sterile chamber.
  • % inhibition ((% mean spore germination in control samples - % mean spore germination in treated samples)/ % mean spore germination in control) X 100
  • FIG.33A Photographs of spore germination of Uncinula necator control are shown in FIG.33A and resveratrol treatment (500 ppm) in FIG.33B.
  • Resveratrol moderately inhibited the spore germination of U. necator, but dose response was not observed.
  • Resveratrol at 63 and 125 ppm exhibited 53 and 48% inhibition respectively, compared to control.
  • Resveratrol at 250 and 500 ppm exhibited 70 and 62% inhibition respectively.
  • the commercial fungicide with Sulphur as active ingredient compound showed 44% inhibition at 2000ppm.
  • Resveratrol inhibited the spore germination of U. necator.
  • Resveratrol can be used to control powdery mildew of grapes in the fields.

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Abstract

L'invention concerne des compositions et des procédés de traitement et de prévention de toute infestation d'une surface ou d'un objet, tel qu'un produit de consommation, une plante issue d'une multiplication ou un matériel végétal issu d'une multiplication, par une population de microbes phytopathogènes ou éventuellement saprophytiques.
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CN113973818A (zh) * 2021-11-05 2022-01-28 陕西师范大学 白藜芦醇或白藜芦醇衍生物在抑制扩展青霉中的应用

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021072473A1 (fr) * 2019-10-14 2021-04-22 IRP Health Pty Ltd Agents antimicrobiens utilisés en tant que conservateurs alimentaires
CN113973818A (zh) * 2021-11-05 2022-01-28 陕西师范大学 白藜芦醇或白藜芦醇衍生物在抑制扩展青霉中的应用
CN113973818B (zh) * 2021-11-05 2023-08-11 陕西师范大学 白藜芦醇或白藜芦醇衍生物在抑制扩展青霉中的应用

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