WO2018210880A1 - Stilbènes pour le traitement pré-récolte et la protection de la récolte - Google Patents

Stilbènes pour le traitement pré-récolte et la protection de la récolte Download PDF

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Publication number
WO2018210880A1
WO2018210880A1 PCT/EP2018/062619 EP2018062619W WO2018210880A1 WO 2018210880 A1 WO2018210880 A1 WO 2018210880A1 EP 2018062619 W EP2018062619 W EP 2018062619W WO 2018210880 A1 WO2018210880 A1 WO 2018210880A1
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ppm
resveratrol
stilbene
composition
composition according
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PCT/EP2018/062619
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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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Publication of WO2018210880A1 publication Critical patent/WO2018210880A1/fr

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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
    • 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 pre-harvest 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.
  • Stilbenes are phenylpropanoids. Stilbenoids are hydroxylated derivatives of stilbene. Many stilbenes and stilbene derivatives are present in plants, for example resveratrol and pterostilbene.
  • Plants produce substances known as phytoaiexins that accumulate rapidly at areas of pathogen i fection 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).
  • microbially-produced stilbenes (such as resveratrol and derivatives thereof) are useful in the treatment of microbial infections of propagated plants and propagated plant material.
  • the invention provides a method of preventing, treating, or reducing an infection by phytopathogenic, facultative saprophytic or saprotrophic microbes in a propagated plant, or propagated plant part, comprising contacting the propagated plant or propagated plant part 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 propagated plant, or propagated plant part, 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.
  • the invention provides a composition for preventing, treating, or reducing an infection by phytopathogenic, facultative saprophytic or saprotrophic microbes in a propagated plant, or propagated plant part, comprising: a stilbene or a methylated or glycosylated derivative thereof; nootkatone; and a carrier.
  • Embodiment 1 A method of preventing, treating, or reducing an infection by phytopathogenic, facultative saprophytic or saprotrophic microbes in a propagated plant, or propagated plant part, comprising contacting the propagated plant or propagated plant part with a composition comprising a stilbene or a methylated or glycosylated derivative thereof.
  • Embodiment 2 The method according to embodiment 1 , wherein the stilbene is resveratrol, dihydroresveratrol or pinosylvin.
  • Embodiment 3 The method according to embodiment 1 or 2, wherein the glycosylated stilbene is piceid (3 -resveratrol monoglucoside or 5-resveratrol monoglucoside), resveratroloside (4'-resveratrol monoglucoside), Mulberroside E (3,4'-resveratrol diglucoside), 3,5- resveratrol diglucoside, or 3,5,4'-resveratrol triglucoside.
  • the glycosylated stilbene is piceid (3 -resveratrol monoglucoside or 5-resveratrol monoglucoside), resveratroloside (4'-resveratrol monoglucoside), Mulberroside E (3,4'-resveratrol diglucoside), 3,5- resveratrol diglucoside, or 3,5,4'-resveratrol triglucoside.
  • Embodiment 4 The method according to any of embodiments 1-3, wherein the glycosylated stilbene is a glycosylated dihydroresveratrol or glycosylated pinosylvin.
  • Embodiment 5 The method according to any of embodiments 1-4, wherein the methylated stilbene is pterostilbene (3,5-dimethoxy-4'-hydroxy-trans-stilbene), 3,5,4'- trimethoxystilbene, pinostilbene, tetramethoxystilbene, pentamethoxystilbene, or N-hydroxy- N- (trimethoxphenyl)-trimethoxy-benzamidine.
  • Embodiment 6 The method according to any of embodiments 1-5, wherein the methylated stilbene is a methylated dihydroresveratrol or methylated pinosylvin.
  • Embodiment 7 The method according to any of embodiments 1-6, wherein the propagated plant or part thereof is a root, a seed, a leaf, a seedling, a shoot, a bud, a fruit, a blossom, a flower, a nut or a mushroom.
  • Embodiment 8 The method according to any of embodiments 1-7, wherein the composition comprising a stilbene or a methylated or glycosylated derivative thereof further comprises: (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
  • Embodiment 9 The method according to any of embodiments 1-9, wherein the composition comprising a stilbene or methylated or glycosylated derivative thereof further comprises nootkatone.
  • Embodiment 10 The composition according to embodiment 9, 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% by weight nootkatone; 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 nootkatone, or about 10 ppm to about 25 ppm,
  • Embodiment 1 1. The method according to any of embodiments 1-10, wherein the composition comprising a stilbene or methylated or glycosylated derivative thereof further comprises at least one additional active ingredient that is a fungicide, fungistatin, bactericide, bacteriostatin, or pesticide.
  • Embodiment 12 The method according to embodiment 1 1 , wherein the at least one additional active ingredient is active against a phytopathogenic, facultative saprophytic, or saprotrophic fungus.
  • Embodiment 13 The method according to embodiment 1 1 or 12, wherein the at least one additional active ingredient is active against a phytopathogenic, facultative saprophytic, or saprotrophic filamentous fungus.
  • Embodiment 14 The method according to any of embodiments 1 1-13, wherein the at least one additional active ingredient is active against a phytopathogenic, facultative saprophytic, or saprotrophic yeast.
  • Embodiment 15 The method according to any of embodiments 1 1-14, wherein the at least one additional active ingredient is active against a phytopathogenic, facultative saprophytic, or saprotrophic bacteria.
  • Embodiment 16 The method according to any of embodiments 1-15, wherein the composition comprising a stilbene or a methylated or glycosylated derivative thereof is formulated in a solid form, a liquid form, a suspension, or an emulsion.
  • 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 18 The method according to any of embodiments 1-17, wherein the method of application is at least partially enclosing in a bag, net, container, or plastic wrap.
  • Embodiment 19 The method according to any of embodiments 1-18, wherein the composition is applied before sowing or planting.
  • Embodiment 20 The method according to any of embodiments 1-18, wherein the composition is applied before or during flowering.
  • Embodiment 21 The method according to any of embodiments 1-18, wherein the composition is applied before harvesting.
  • Embodiment 22 The method according to any of embodiments 1-18, wherein the composition is applied during harvest of the propagated plant or propagated plant part.
  • Embodiment 23 The method according to any of embodiments 1-18, wherein the composition is applied after the harvest, before transportation, or before storage of the propagated plant or propagated plant part.
  • Embodiment 24 The method according to any of embodiments 1-23, wherein the composition is applied during a period of quarantine.
  • Embodiment 25 The method according to any of embodiments 1-24, wherein the composition is applied during a period of high humidity (e.g., about 70% or higher) and/or high temperature (e.g., about 20°C or higher).
  • Embodiment 26 The method according to any of embodiments 1-25, wherein propagated plant material comes from a propagated plant that is a cereal, a beet, a leguminous plant, an oil crop, a cucurbit, a fibre plant, a citrus plant, a vegetable plant, a plant in the laurel family, maize, canola, tobacco, a nut tree, coffee, sugar cane, tea, grape, hop, a plantain, a latex plant, or an ornamental plant.
  • a propagated plant that is a cereal, a beet, a leguminous plant, an oil crop, a cucurbit, a fibre plant, a citrus plant, a vegetable plant, a plant in the laurel family, maize, canola, tobacco, a nut tree, coffee, sugar cane, tea, grape, hop, a plantain, a latex plant, or an ornamental plant.
  • Embodiment 27 A composition for preventing, treating or reducing an infection by phytopathogenic, facultative saprophytic or saprotrophic microbes in a propagated plant, or propagated plant part, comprising a stilbene or a methylated or glycosylated derivative thereof.
  • Embodiment 28 The composition according to embodiment 27, wherein the stilbene is resveratrol, dihydroresveratrol or pinosilvin.
  • Embodiment 29 The composition according to embodiment 27 or 28, wherein the glycosylated stilbene is piceid (3 -resveratrol monoglucoside or 5-resverarol monoglucoside), resveratroloside (4'-resveratrol monoglucoside), Mulberroside E (3,4'- resveratrol diglucoside), 3,5- resveratrol diglucoside, or 3,5,4'-resveratrol triglucoside.
  • the glycosylated stilbene is piceid (3 -resveratrol monoglucoside or 5-resverarol monoglucoside), resveratroloside (4'-resveratrol monoglucoside), Mulberroside E (3,4'- resveratrol diglucoside), 3,5- resveratrol diglucoside, or 3,5,4'-resveratrol triglucoside.
  • Embodiment 30 The composition according to any of embodiments 27-29, wherein the glycosylated stilbene is a glycosylated dihydroresveratrol or glycosylated pinosylvin.
  • Embodiment 31 The composition according to any of embodiments 27-30, wherein the methylated stilbene is pterostilbene (3,5-dimethoxy-4'-hydroxy-trans-stilbene), 3,5,4'-trimethoxystilbene, pinostilbene, tetramethoxystilbene, pentamethoxystilbene, or N- hydroxy-N- (trimethoxphenyl)-trimethoxy-benzamidine.
  • the methylated stilbene is pterostilbene (3,5-dimethoxy-4'-hydroxy-trans-stilbene), 3,5,4'-trimethoxystilbene, pinostilbene, tetramethoxystilbene, pentamethoxystilbene, or N- hydroxy-N- (trimethoxphenyl)-trimethoxy-benzamidine.
  • Embodiment 32 The composition according to any of embodiments 27-31 , wherein the methylated stilbene is a methylated dihydroresveratrol or methylated pinosylvin.
  • Embodiment 33 The composition according to any of embodiments 27-32, 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 1 ,000 ppm, or at least about 5,000 ppm of the stilbene, or about 10
  • Embodiment 34 The composition according to any of embodiments 27-33, further comprising at least one additional active ingredient that is a fungicide, fungistatin, bactericide, bacteriostatin, or pesticide.
  • Embodiment 35 The composition according to embodiment 34, wherein the at least one additional active ingredient is active against a phytopathogenic, facultative saprophytic, or saprotrophic fungus.
  • Embodiment 36 The composition according to embodiment 34 or 35, wherein the at least one additional active ingredient is active against a phytopathogenic, facultative saprophytic, or saprotrophic filamentous fungus.
  • 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 39 The composition according to any of embodiments 34-38, wherein the composition is formulated in a solid form, a liquid form, a suspension, or an emulsion.
  • Embodiment 40 A composition for preventing, treating, or reducing an infection by phytopathogenic, facultative saprophytic or saprotrophic microbes in a propagated plant, or propagated plant part, comprising: a) a stilbene or a methylated or glycosylated derivative thereof; b) nootkatone; and c) a carrier.
  • Embodiment 41 The composition according to embodiment 40, wherein the stilbene is resveratrol, dihydroresveratrol, or pinosylvin.
  • Embodiment 42 The composition according to embodiment 40 or 41 , wherein the glycosylated stilbene is at least one of 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.
  • Embodiment 43 The composition according to any of embodiments 40-42, wherein the glycosylated stilbene is a glycosylated dihydroresveratrol.
  • Embodiment 44 The composition according to any of embodiments 40-43, wherein the glycosylated stilbene is a glycosylated pinosylvin
  • Embodiment 45 The composition according to any of embodiments 40-44, wherein the methylated stilbene is pterostilbene (3,5-dimethoxy-4'-hydroxy-trans-stilbene), 3,5,4'-trimethoxystilbene, pinostilbene, tetramethoxystilbene, pentamethoxystilbene, or N- hydroxy-N- (trimethoxphenyl)-trimethoxy-benzamidine.
  • the methylated stilbene is pterostilbene (3,5-dimethoxy-4'-hydroxy-trans-stilbene), 3,5,4'-trimethoxystilbene, pinostilbene, tetramethoxystilbene, pentamethoxystilbene, or N- hydroxy-N- (trimethoxphenyl)-trimethoxy-benzamidine.
  • Embodiment 46 The composition according to any of embodiments 40-45, wherein the methylated stilbene is a methylated dihydroresveratrol.
  • Embodiment 47 The composition according to any of embodiments 40-46, wherein the methylated stilbene is a methylated pinosylvin.
  • 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 greater than 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 49 The composition according to any of embodiments 40-48, 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 greater by weight nootkatone; 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 nootkatone, or about 10
  • Embodiment 50 The composition according to any of embodiments 40-49, further comprising at least one additional active ingredient that is a fungicide, fungistatin, bactericide, bacteriostatin, or pesticide.
  • Embodiment 51 The composition according to embodiment 50, wherein the at least one additional active ingredient is active against a phytopathogenic, facultative saprophytic, or saprotrophic fungus.
  • 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 54 The composition according to any of embodiments 50-53, wherein the at least one additional active ingredient is active against a phytopathogenic, facultative saprophytic, or saprotrophic bacteria.
  • Embodiment 55 The composition according to any of embodiments 50-54, wherein the composition is formulated in a solid form, a liquid form, a suspension, or an emulsion.
  • Embodiment 56 Use of the composition according to any of embodiments 40-55 for preventing, treating, or reducing an infection by phytopathogenic, facultative saprophytic or saprotrophic microbes in a pre-harvest propagated plant or propagated plant material.
  • 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 in a pre-harvest propagated plant or propagated plant material.
  • FIG.l illustrates a biosynthetic pathway for resveratrol.
  • FIG.2 shows the structure and aqueous solubility of resveratrol 3,4'diglucoside.
  • FIG.3 shows the shows the names, molecular weights and aqueous solubilities of various resveratrol glycoside molecules.
  • FIG.4 shows the structure of nookatone.
  • FIG.5A-C show Alternaria sp. on cherry (FIG.5A), musk melon (FIG.5B), and apple (FIG.5C).
  • FIG.6 shows that various concentrations of resveratrol inhibit Alternaria sp.
  • FIG.7 shows that 250 ppm resveratrol inhibits Alternaria sp. mycelial growth.
  • FIG.8A shows mycelial growth inhibition of Alternaria sp. on Potato Dextrose Agar (PDA) plates compared to control following treatment with nootkatone (NKT at 240ppm) alone, resveratrol (RESV at 240ppm) alone, and the combination of resveratrol and nootkatone (NKT + RESV at 240ppm each of NKT and RESV).
  • PDA Potato Dextrose Agar
  • FIG.8B shows percent mycelial growth inhibition of Alternaria sp. compared to control following treatment with nootkatone (NKT) alone, resveratrol (RES) alone, and nootkatone plus resveratrol (NKT + RES) at the concentrations shown (ppm).
  • FIG.9 shows that 250 ppm resveratrol prevents spore germination of Alternaria alternata. The small beak-like germ tubes did not elongate (about 80-90% inhibition).
  • 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.ll shows spore germination of B. theobromae (BT) at 24 hours in a control plate (BT control; scale bar is 50 microns), and in plates treated with nootkatone (NKT at 500ppm and NKT at 250 ppm; scale bar is 50 microns), the combination of resveratrol and nootkatone (REVS+NKT at 500ppm each, and at 250 ppm each; scale bar is 50 microns), and 10 ppm Tebuconazole (lOppm Tebuconazole; scale bar is 50 microns).
  • BT control shows spore germination of B. theobromae (BT) at 24 hours in a control plate (BT control; scale bar is 50 microns), and in plates treated with nootkatone (NKT at 500ppm and NKT at 250 ppm; scale bar is 50 microns), the combination of resveratrol and nootkatone (REVS+NKT at 500ppm each, and
  • FIG.12 shows that various concentrations (10 - 250 ppm) of resveratrol inhibit B. cinerea growth in vitro after seven days of incubation.
  • 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.15 shows that combinations of resveratrol and nootkatone inhibit B. cinerea growth in vitro after five days of incubation.
  • FIG.16 shows Botryris cinerea spore germination inhibition at 18 hours under control conditions (Botrytis cinerea (strawberry); scale bar is 20 microns), and after nootkatone treatment at 62.5 ppm (NKT @62.5ppm), resveratrol treatment at 62.5ppm (RESV@62.5; scale bar is 20 microns), 125ppm (RESV@125; scale bar is 50 microns), 250ppm (RESV@250; scale bar is 50 microns), and treatment with a combination of nootkatone and resveratrol at 62.5ppm each (NKT+RESV @62.5ppm; scale bar is 20 microns).
  • FIG.17 shows B. cinerea mycelial percent growth inhibition by nootkatone (NKT), resveratrol (RES), or the combination of nootkatone and resveratrol mixed at a 1 : 1 ratio (RES+NKT) at the concentrations shown (ppm).
  • FIG.18A shows inhibition of mycelial growth rate in B. cinerea by nootkatone alone (NKT), resveratrol alone (RES), or the combination of nootkatone and resveratrol (NKT+RES), from Day 1 to Day 5.
  • FIG.18B shows inhibition of mycelial growth rate in B. cinerea by nootkatone alone (NKT), resveratrol alone (RES), or the combination of nootkatone and resveratrol (RES+NKT), from Day 5 to Day 10.
  • 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.21 shows that various concentrations of resveratrol inhibit Fusarium oxysporium growth in vitro after seven 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.
  • FIG.26B shows percent mycelial growth inhibition of M. laxa by treatment with nootkatone alone (NKT), resveratrol alone (RES), or treatment the combination of resveratrol and nootkatone (RES+NKT) at the concentrations shown (ppm).
  • FIGS. 26C shows mycelial growth inhibition of M. laxa by resveratrol alone.
  • FIGS. 26D shows mycelial growth inhibition of M. laxa by resveratrol alone.
  • FIG.27 shows that resveratrol can prevent and cure C. gloeosporioides in apples. Apples were washed in tap water and wiped with paper towel. The apple surface was sterilized in 0.2% mercuric chloride and rinsed in sterile distilled water three times to remove traces of HgCl 2 . Five spots of 1.5cm diameter were marked and gently pricked with needle of 2ml syringe, to create mechanical damage. In apples under natural conditions, pathogens from outside enter through mechanical damage.
  • 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.29B shows the percent mycelial growth inhibition of Magnaporthe grisea by treatment with resveratrol at the concentrations shown, or by treatment with carbendazim.
  • FIG.30A shows Magnaporthe grisea conidia germination inhibition following 24 hours of treatment with resveratrol (RESV) at the concentrations shown (ppm).
  • RESV resveratrol
  • FIG.30B shows Magnaporthe grisea conidia germination inhibition following 24 hours of treatment with the combination of resveratrol and nootkatone (RESV+NKT) at the concentrations shown (ppm).
  • FIG.31A shows a photograph of spore germination of Uncinula necator in control after 20 hours.
  • FIG.31B shows a photograph of spore germination of Uncinula necator with resveratrol treatment (500 ppm) after 20 hours.
  • 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.”
  • pre-harvest refers to a period of time prior to harvesting of a food material.
  • pre-harvest includes any time starting with when a seed is planted to when a fully mature crop is ready for harvest.
  • food material or “food materials” refers to pre-harvest and post-harvest propagated plants and propagated plant parts or materials, meats, dairy products, and derivatives thereof.
  • Food materials can include processed foods, prepared foods, and food ingredients.
  • food materials include flours, food additives, grain derivatives, sugars, amino acids, and the like.
  • Food materials are typically meant for consumption by humans or other animals.
  • One example of food materials is cultivated crops.
  • the term "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 propagated plants, portions thereof, or propagated plant material.
  • the active ingredients may be effective against phytopathogenic microbes including but 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, in particular, Pseudocercosporella herpotrichoides); Oomycetes (for example Phytophthora, Peronospora, Bremia, Pythium, Plasmopara); Firmicutes (Baci), Firm
  • the term "antimicrobial” is understood as being effective in preventing or reducing infection of propagated plants or propagated plant material, 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 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, Puce in ia) Fungi imperfecti (for example Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyricularia and, Pseudocercosporella herpotrichoides); Oomycetes (for example Phytophthora, Peronospora, Bremia, Pythium, Plasmopara); Firmi
  • prevention or treatment of phytopathogenic microbial infections is used interchangeably with “prevention or treatment of facultative saprophytic microbial infections” and refers to a process by which a population of microbes capable of infecting and damaging propagated plant material are at least one of: killed, growth- inhibited, or inhibited from reproducing, on an object, a surface, propagated plant, portion of a propagated plant, or propagated plant material or plant fruit or seed.
  • prevention or treatment of phytopathogenic microbes may include any manner of treatment performed to reduce the population of phytopathogenic microbes.
  • 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 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, or are surfaces and objects which could act as vectors for the transportation of phytopathogenic microbes between infected and uninfected host propagated plants or propagated plant material.
  • surfaces include, without limitation, work surfaces, conveyor belts, doors, wall moldings, walls, sheets of glass, or any surface of a vehicle, equipment, packaging material or tool used to handle or transport one or more propagated plants or propagated plant material, plant fruit or plant seed.
  • an environment rich in propagated plant material As used herein, the terms "an environment rich in propagated plant material,” “agricultural areas”, “forestry areas” and “locations with high concentrations of propagated plant material or crops or parts thereof susceptible to damage by phytopathogenic microbes” are used interchangeably and refer to one or more environments capable of harboring high concentrations of phytopathogenic microbes. These areas may be outdoors or at least partially enclosed as an indoor or sheltered environment capable of sustaining a different microclimate to the external environment.
  • 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, or containers used to transport or store propagated plant material, including but not limited to bags, boxes, crates, nets, jars, tubs, sacks, silos, conveyor belts, trailers, storage bins, refrigerators, freezers, packaging material, or plastic wrap.
  • 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
  • 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.
  • 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
  • the term "effective concentration” refers to a concentration of an active ingredient (such as resveratrol or a derivative thereof) within a composition such that when the composition is applied to a propagated plant or propagated plant material or to a relevant surface, a population of phytopathogenic microbes are at least one of killed, growth- inhibited, or inhibited from reproducing.
  • an active ingredient such as resveratrol or a derivative thereof
  • 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 -hydroxy ferulic acid, sinapinic acid, cinnamoyl-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, resveratrol, pinosylvin, pinocembrin chalcone, and pinocembrin.
  • dihydrophenylpropanoid refers to compounds based on a phenylpropanoate backbone. Examples of such compounds include, but are not limited to, diliydrocinnamic acid, phlo etic acid, 3,4-dihydroxyhydrocinnamic acid, hydroferulic acid, dihydrocoumaroyl-CoA, dihydrocinnamoyl-CoA, and the like.
  • dihydrophenylpropanoid derivative refers to any compound derived from, synthesized from, or biosynthesized from a dihydrophenylpropanoid; i.e. a dihydrophenylpropanoid derivative includes any compound for which a dihydrophenylpropanoid compound is a precursor or intermediate. Examples of dihydrophenylpropanoid derivatives include, but are not limited to, dihydrostilbenoid compounds and dihydrochalcone compounds.
  • dihydrophenylpropanoid derivatives include, but are not limited to, phloretin, phlorizin, dihydropinosylvin, dihydropinosylvincarboxylate, 3 -O-methyldihydropinosylvincarboxylate, 4-isoprenyl-3 -O- methyldihydropinosylvincarboxylate (amorfrutin 1), 3-O-methyldihydropinosylvin, 4- isoprenyl-3-O-methyldihydropinosylvin (amorfrutin 2), 5-hydroxy-lunularic acid, and dihydroresveratrol.
  • phloretin phlorizin
  • dihydropinosylvin dihydropinosylvincarboxylate
  • 3 -O-methyldihydropinosylvincarboxylate 4-isoprenyl-3 -O- methyldihydropinosylvincarboxylate
  • 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.
  • 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 propagated plants, trees, flowers, fruit, propagated plant material or agricultural produce for use in seed, food or feed.
  • 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 propagated plants and propagated plant material.
  • the current disclosure provides methods and uses for a composition comprising stilbene suitable for treating a surface, 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 propagated plants or propagated plant material.
  • some embodiments of the current disclosure are useful for increasing or retaining the commercial value of a propagated plant or propagated plant material by applying a stilbene-containing composition to the propagated plant or propagated plant material to at least one of either prevent infection of the propagated plant or propagated plant material with a population of phytopathogenic or facultative saprophytic microbes, or treat such an infection to result in a maintained and/or improved propagated plant health and/or aesthetic appearance of the propagated plant.
  • 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 propagation, 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 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 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 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 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.
  • Agrotextiles are used as a ground cover and typically applied after sowing or planting a crop or ornamental plant.
  • Agrotextiles can be air, water vapour, water, and/or light permeable and are effective at elevating ground temperature and retaining water content.
  • farmers, greenhouse owners and domestic users deploy agrotextiles to create a microclimate highly favourable for accelerated plant growth and for earlier planting or sowing with reduced risk of frost.
  • agrotextiles make the conventional use of pesticides problematic and the created microclimate conditions of higher temperature (e.g., about 20°C or higher) and higher humidity (e.g., about 70% or higher) may also encourage the growth of pests and in particular of phytopathogenic, facultative saprophytic or saprotrophic microbes.
  • higher temperature e.g., about 20°C or higher
  • higher humidity e.g., about 70% or higher
  • Examples of agrotextiles coated with or including stilbene may be at least a portion of a forcing cover, polytunnel, plant cover, fruit cover, insect screen, shade screen, blanching screen, ventilation screen, agro bag, crop net, fruit net, or nut bag.
  • a forcing cover polytunnel
  • plant cover fruit cover
  • insect screen shade screen
  • blanching screen ventilation screen
  • agro bag crop net, fruit net, or nut bag.
  • the provision of shade by a suspended agrotextile is beneficial for some propagated plants, but also for air drying some types of propagated plant material including but not limited to fruits (such as grapes, tomatoes, peppercorn, spices, herbs) and flowers (such as hops, lavender, sunflowers, roses and orchids).
  • Agro bags, fruit nets and plastic film coated with or impregnated with a composition including stilbene can also reduce the damage phytopathogenic, facultative saprophytic or saprotrophic microbes can cause to harvested crops or harvested propagated plant material.
  • an agrotextile or plastic film coated, contacted or impregnated with a composition comprising stilbene is suitable for use in agriculture, horticulture, forestry, gardens, greenhouses, areas used to store or transport propagated plant material, food processing or kitchens. Further combinations of resveratrol-containing compositions and agricultural or food industry devices and methods are contemplated as described herein elsewhere.
  • the active ingredients contemplated herein are used in the form of compositions.
  • the active ingredients can be applied to the propagated plant or to the propagated plant material 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 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%) 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.
  • stilbene 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.
  • 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 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 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.
  • 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.
  • propagated plant material or propagated plants can be treated prior to harvest, concomitant with harvest, prior to transportation or during a period of quarantine.
  • propagated plant material or propagated plants can be treated in combination with a biocide, for example, when plant breeding to produce resistant varieties.
  • propagated plant material or propagated plants can be treated during a period of high humidity and/or high temperature.
  • 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.
  • 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.
  • 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.
  • 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. In some embodiments, 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 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 1 ,000 ppm.
  • the 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 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 15 seconds.
  • methods of application to a subject, surface 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
  • Such agricultural substances may themselves be dispensed or applied by spreaders and other means as known in the art.
  • 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.
  • 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.
  • 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, 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 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 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.
  • treatment may be two-fold: physical removal and chemical disinfection and/or inhibition.
  • 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 plants.
  • the microbiological infection index of infection
  • Assessment of disease incidence can be suitable for determining early stage infection and can provide a general indication of the prevalence in a given population of plants.
  • Disease severity can be another way to represent a microbial infection and can be more appropriate in diseases like rusts, downy and powdery mildew, leaf spots or other similar diseases. Disease severity can be represented by the percentage of the plant covered by a symptom, lesion or damage caused by the disease (for example, 1, 5, 10, 20 or 50% of leaf area infected).
  • 6-week-old tobacco plants (cv. "Burley") are sprayed to drip point with a spray mixture prepared from a formulated active ingredient or a spray mixture not containing the active ingredient (control).
  • a spray mixture prepared from a formulated active ingredient or a spray mixture not containing the active ingredient (control).
  • the treated and untreated plants are infected with a spore suspension of Cercospora nicotianae (Ciba No. 295; max. 150,000 per ml), and subsequently incubated for 5 days at 20-22°C and a relative atmospheric humidity of 70- 90%). 10 days post-infection, the incidence and/or severity of fungal infestation is assessed and compared with the infestation on untreated plants.
  • the treated plants show a significant lower index of infection than the untreated plants.
  • 40 cucumbers (Cucumis sativus) are dipped in a liquid containing active ingredient or in a similar liquid not containing the active ingredient (control). After 24h, the treated and untreated cucumbers are infected with a conidia suspension of the Sphaerotheca fuliginea fungus. Treated and untreated cucumbers are subsequently incubated for 7 days at a relative atmospheric humidity of 90-100% and 20° C. 10 days post-infection, the incidence and/or severity of microbiological infestation is assessed. The treated plants show a significant lower index of infection than the untreated cucumbers.
  • Pyricularia oryzae fungus is measured 44 days post-application. The treated plants show a significant lower index of infection than the untreated plants.
  • 6-week-old tobacco plants (cv. "Burley") are sprayed to drip point with a spray mixture prepared from a formulated active ingredient or a spray mixture not containing the active ingredient (control).
  • a spray mixture prepared from a formulated active ingredient or a spray mixture not containing the active ingredient (control).
  • the treated and untreated plants are infected with a spore suspension of Cercospora nicotianae (Ciba No. 295; max. 150,000 per ml), and subsequently incubated for 5 days at 20-22°C and a relative atmospheric humidity of 70- 90%.
  • 10 days post-infection the incidence and/or severity of fungal infestation is assessed and compared with the infestation on untreated plants.
  • the treated plants show a significant lower index of infection than the untreated plants.
  • 16- to 19-day-old cucumber plants (“Wisconsin”) are sprayed to drip point with a spray mixture prepared from a formulated active ingredient or a spray mixture not containing the active ingredient (control).
  • the treated and untreated plants are infected with a sporangia of Pseudoperonospora cubensis (strain 365, Ciba; max. 5000 per ml), and the treated plants are subsequently incubated for 1-2 days at 18-20° C. 10 days postinfection, the incidence and/or severity of microbiological infestation is assessed.
  • the treated plants show a significant lower index of infection than the untreated plants.
  • aphids Twenty to thirty apterous adult aphids are introduced to 8-week-old tomato plants. Fourteen days after the aphids are introduced, the infested plants are sprayed to drip point with a spray mixture prepared from a formulated combination of active ingredients resveratrol and nootkatone or a spray mixture not containing the active ingredients (control). After 24 hours, the treated and untreated plants are infected with a spore suspension of Phytophythora infestans (max. 150,000 per ml), and subsequently incubated for 5 days at 20- 22°C and a relative atmospheric humidity of 70-90%. 10 days post-infection, the incidence and/or severity of fungal infestation is assessed and compared with the infestation on untreated plants. The treated plants show a significant lower index of infection than the untreated plants.
  • Colletotrichum gloeosporioides, Fusarium sp. Alternaria alternata apple pathotype mali (A. mali), Botrytis cinerea, and Trichothecium roseum were all isolated from infected fruits.
  • Potato Dextrose Agar (PDA) from Hi media (MH096-500G) was used throughout. Thirty-nine grams of PDA was dissolved in 900 ml of double distilled water and mixed well. Media pH was checked and pH was adjusted to 5.0-5.5 with IN NaOH and IN HC1.
  • 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.5). 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).
  • the EC 50 for resveratrol was determined to be 250 ppm (250 ⁇ g/ml), and the EC 50 for resveratrol when combined with 120 ppm of nootkatone was determined to be 120 ppm (120 ⁇ g/ml).
  • 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.
  • 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.
  • FIG. 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 ⁇ g/ml.
  • 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 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 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).
  • 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.
  • 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 ⁇ g/ml).
  • 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 observed and there was no spore germination at 125 ppm of resveratrol, and only 20-30% spores germinated in 31.25ppm of resveratrol. All the spores germinated at 10 ppm of carbendazim and tebuconazole, and germ tube length was reduced to 50%> to that of control.
  • Example 8 Inhibition of Monilini 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 of air-conditioned store and left on table for 2 days to allow disease 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 10-13xl0 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 ⁇ 7 ⁇ . 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.
  • 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 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.
  • Method of Testing 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
  • Results The results are shown in Table 16. Table No. 16. Effects of Resveratrol Treatment on spore germination of Uncinula necator.
  • FIG.31A Photographs of spore germination of Uncinula necator control are shown in FIG.31A and resveratrol treatment (500 ppm) in FIG.3 IB.
  • 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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  • Agronomy & Crop Science (AREA)
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Abstract

L'invention concerne des compositions et des procédés de traitement et de prévention d'infections d'une plante propagée ou d'une matière végétale propagée, par une population de microbes végétaux phytopathogènes ou saprophytes facultatifs.
PCT/EP2018/062619 2017-05-15 2018-05-15 Stilbènes pour le traitement pré-récolte et la protection de la récolte WO2018210880A1 (fr)

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CN108271780A (zh) * 2018-01-12 2018-07-13 临沂大学 虎杖浸膏及其主要成分白藜芦醇在农业中的应用

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108271780A (zh) * 2018-01-12 2018-07-13 临沂大学 虎杖浸膏及其主要成分白藜芦醇在农业中的应用

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