WO2020193679A1 - Protection de culture contre une infection fongique - Google Patents

Protection de culture contre une infection fongique Download PDF

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Publication number
WO2020193679A1
WO2020193679A1 PCT/EP2020/058478 EP2020058478W WO2020193679A1 WO 2020193679 A1 WO2020193679 A1 WO 2020193679A1 EP 2020058478 W EP2020058478 W EP 2020058478W WO 2020193679 A1 WO2020193679 A1 WO 2020193679A1
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WIPO (PCT)
Prior art keywords
natamycin
composition
zinc oxide
acid
composition according
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PCT/EP2020/058478
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English (en)
Inventor
Albert-Jon Vis
Manoj Kumar
Gabriel Marinus Henricus Meesters
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Dsm Ip Assets B.V.
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Publication of WO2020193679A1 publication Critical patent/WO2020193679A1/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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention discloses a composition comprising natamycin and zinc oxide for protecting crop against fungal infection.
  • phenylpyrrole compounds such as fludioxonil and/or methionine biosynthesis inhibitors like cyprodinil or other agricultural fungicides.
  • Use of these synthetic products is however not sustainable. In many countries they are banned or expected to be banned soon.
  • several fungi have developed partial or even complete resistance to certain fungicides.
  • Naturally occurring polyene fungicides can be used to prevent fungal growth in a wide variety of applications.
  • An example of such a polyene fungicide is natamycin.
  • natamycin has been used to prevent fungal growth on food products such as cheese, sausages, yoghurt and, in some countries, juices and wine.
  • This natural preservative which is produced by fermentation using Streptomyces natalensis, is widely used throughout the world as a food preservative and has a long history of safe use in the food industry. It is very effective against all known food spoilage molds.
  • natamycin is applied for many years in e.g. the cheese industry, up to now development of resistant mold species was never observed.
  • Natamycin is preferable to many other preservatives as it is free from odor and color so that it causes no taste aversion and therefore does not adversely affect consumer acceptance.
  • Natamycin has a minimal inhibitory concentration of less than 5 ppm for most yeasts and of less than 10 ppm for most foodborne fungi.
  • the solubility of natamycin in water at neutral pH levels is 30 ppm (Brik, H.; "Natamycin” Analytical Profiles of Drug Substances 10, 513-561 (1981)). Therefore, for many applications, a treatment with a natamycin suspension is quite effective: the level of dissolved active natamycin is high enough to prevent the outgrowth of fungi while the undissolved fraction forms a depot.
  • Natamycin may also be used to prevent fungal growth on crop, as generally suggested in WO 2004/105491 , or specifically for banana plants in WO 2005/074687 or by treatment of strawberry plant roots in WO 2018/01 1046.
  • natamycin is sensitive to ultraviolet light which has a severe impact on the stability and, ostensibly, the efficacy of natamycin.
  • Natamycin is often added to the surface of food products e.g. cheeses to prolong their shelf life.
  • it can already be degraded on the food products by the time of purchase by consumers due to the exposure of the products to high-intensity supermarket fluorescent lighting commonly used in retail display cases.
  • full balanced spectrum lamps emitting much lower levels of ultraviolet light can prevent natamycin degradation due to ultraviolet light and consequently preserve the efficacy of natamycin.
  • the use specific packaging materials blocking destructive ultraviolet radiation was suggested to prevent natamycin degradation (see Koontz et al. (2003), J. Agric. Food Chem. 51 : 71 1 1 -71 14).
  • WO 2002/081717 describes that natamycin can be protected from the harmful influence of ultraviolet light when used on agricultural products by encapsulation in alginate or polyvinyl acetate or by producing derivatives of natamycin that have been chemically or enzymatically modified to become less sensitive to ultraviolet light.
  • a disadvantage of the use of encapsulated or modified forms of natamycin is often their lower activity towards fungi. Another disadvantage is that such solutions more often than not are expensive and thus not economically viable.
  • the present invention solves the problem by providing a new stable and long-term effective antifungal composition comprising natamycin.
  • wt.% refers to a weight percentage of a given component in a composition relative to the total weight of that composition.
  • natamycin including, but not limited to, salts or solvates of natamycin or modified forms of natamycin may also be applied in the compositions of the invention.
  • An example of a commercial product containing natamycin is the product with the brand name Delvocid ® . Delvocid ® is produced by DSM Food Specialties (The Netherlands) and contains 50% (w/w) natamycin. Said commercial products can be incorporated in the compositions of the invention.
  • transition metal oxides outperformed organic molecules when combined with natamycin.
  • presence of certain transition metal oxides in antifungal compositions has been disclosed e.g. in WO 2017/216722, the focus of this document is on synergistic antifungal activity between medium chain fatty acids and antifungal agents. The combination of natamycin with transition metal oxides is not disclosed, let alone the effect of transition metal oxides on the stability of natamycin.
  • natamycin with cinnamic acid-based antioxidants such as ferulic acid
  • sunscreens such as e.g. octocrylene
  • a cinnamic acid-based antioxidant like e.g. methoxy cinnamate
  • a transition metal oxide like titanium dioxide or zinc oxide does result in a formulation that has efficacy against Botrytis cinerea after three days under exposure to light.
  • natamycin with cinnamic acid-based antioxidants display phytotoxicity, for example in field studies on strawberry.
  • Phytotoxicity is a phenomenon that does not occur with the combination of natamycin with a transition metal oxide.
  • field studies on various crop such as strawberry i.e. cv. Fronteras, cv. Monterey, cv. Splendor
  • natamycin/ferulic acid mostly does not improve the efficacy in managing gray mold as compared to natamycin alone.
  • the invention provides a composition comprising natamycin and zinc oxide.
  • natamycin/zinc oxide not only additionally increases natamycin stability in in vitro studies, but also improves performance in field trials when compared to natamycin alone on inoculated fruit harvested 7 days after application of the natamycin formulation.
  • the antimicrobial composition according to the invention is stable due the presence of a transition metal oxide in the composition.
  • the composition according to the invention may comprise one or more ultraviolet absorbers. In other words, it may comprise a combination of absorbers. If more than one ultraviolet absorber is used, the absorbers preferably absorb ultraviolet light at different wavelengths, resulting in a wider range of wavelength of ultraviolet light blocked.
  • the term“ultraviolet absorber” refers to an agent that protects an active compound, such as a polyene antifungal agent e.g. natamycin, from inactivation through e.g. photodegradation by absorbing in the ultraviolet wavelength range, i.e. 200 to 400 nm.
  • the active compound in the composition according to the invention remains stable, i.e. maintains its antifungal activity.
  • the active compound has an excellent photostability in the compositions according to the invention.
  • the antifungal activity of the active compound in the composition according to the invention is at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 95% and preferably at least 97%, more preferably at least 98%, even more preferably at least 99% and particularly 100% of the initial activity of the active compound, i.e.
  • the composition according to the invention comprises the above residual antifungal activity when exposed to at least 2500 pW/cm 2 UV A and 200 pW/cm 2 UV B fluorescent lighting at 25°C for at least 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 75, 85, 95, 105, 125, 150, 175, 200, 225, 250, 275, 300, 325, 350 days.
  • the composition of the invention may be an aqueous composition.
  • Concentrations of the transition metal oxide like titanium dioxide or zinc oxide in such aqueous compositions are from 0.1 - 10 wt.%, or from 0.5 - 5 wt.%, relative to the total weight of the composition. While the higher end of the range leads to higher protection, the overall amount of additive should be chosen as low as possible for economic reasons. Also, favorable transition metal oxides are white compounds, a color which, at increasing concentration, may become visible on plant leaves. The skilled person in this respect will balance parameters and arrive at suitable concentrations. For example, suitable concentrations of zinc oxide are 0.5 ⁇ 0.3 wt.% or 0.5 ⁇ 0.2 wt.%.
  • Concentrations of natamycin in the above aqueous compositions are from 0.01 -1 wt.%. Since also concentrated solutions or suspensions, that may be diluted prior to use, are included in the invention, the amounts of natamycin and transition metal oxide may be defined as a ratio. Thus, suitable ratios in the aqueous composition are wherein the natamyci zinc oxide ratio is from 1 :5 to 1 :50, or from 1 :10 to 1 :25. Also, two or more transition metal oxides may be present in the composition. For example, both titanium dioxide and zinc oxide may be present in which case the sum of the two is as referred to in the above ranges.
  • composition of the invention when the composition of the invention is an aqueous composition it may have a pH of from 3.5 to 8, preferably of from 5 to 7.
  • the compositions of the present invention can be aqueous or non-aqueous ready-to-use compositions but may also be aqueous or non-aqueous concentrated compositions/suspensions or stock compositions, suspensions and/or solutions which before use must be diluted with a suitable diluent such as water or a buffer system.
  • the compositions of the invention can also be used to prepare coating emulsions.
  • the compositions of the present invention also include concentrated dry products such as e.g. powders, granulates and tablets. They can be used to prepare compositions for immersion or spraying of products such as agricultural products including plants, crops, vegetables and/or fruits.
  • Titanium dioxide is a compound that not only is inexpensive, but also has a favorable toxicity; the compound is established non-toxic to fish and thus there are no risks associated with contact to ground water, rivers, lakes or oceans. The compound also is well accepted as constituent of wall paint. Titanium dioxide or zinc oxide may be microparticulated.
  • microparticulated refers to a particle size from about 5 nm to about 200 nm, particularly from about 15 nm to about 100 nm.
  • the titanium dioxide or zinc oxide particles may also be coated by metal oxides such as e.g. aluminum or zirconium oxides or by organic coatings such as e.g. polyols, methicone, aluminum stearate, alkyl silane.
  • metal oxides such as e.g. aluminum or zirconium oxides
  • organic coatings such as e.g. polyols, methicone, aluminum stearate, alkyl silane.
  • composition of the invention may further comprise at least one additional compound selected from the group consisting of a sticking agent, a surfactant, an emulsifier, a detergent, a preservative, a stabilizer, a spreading agent, an antioxidant, an anti-foam- forming agent, a wetting agent, a thickening agent, a further antimicrobial agent, a filler, a spray oil, a dispersing agent, and a flow additive.
  • a sticking agent a surfactant, an emulsifier, a detergent, a preservative, a stabilizer, a spreading agent, an antioxidant, an anti-foam- forming agent, a wetting agent, a thickening agent, a further antimicrobial agent, a filler, a spray oil, a dispersing agent, and a flow additive.
  • sticking agents examples include, but are not limited to, latex based products like Prolong ® (Holland Fyto B.V., The Netherlands) and Bond ® (Loveland Industries Ltd), pilonene/terpene-based products like Nu-film ® (Hygrotech Saad) and Spray-Fast ® (Mandops) and long chain polysaccharides like xanthan gum, gellan gum and guar gum.
  • the sticking agent may be a polymer or co-polymer from a type of polymer such as polyacrylate and polyethylene e.g. Neocryl ® (DSM, The Netherlands).
  • the composition of the invention may also comprise two or more different sticking agents.
  • surfactants examples include, but are not limited to, anionic tensides such as sodium lauryl sulphate or polyethylene alkyl ethers or polyoxyethy I ethers, e.g. Tween ® 60, 61 or 65.
  • useful surfactants are organo silicones, sulfosuccinates, alcohol ethoxylates, fatty acid ethoxylates, fatty acid propoxylates and the commercial product Zipper ® (Asepta BV, The Netherlands).
  • the composition of the invention may also comprise two or more different of the above-mentioned agents.
  • suitable preservatives include, but are not limited to, weak acid preservatives such as sorbic acid, lactic acid, benzoic acid, propionic acid, citric acid, acetic acid, or an alkali metal or alkali earth metal salt thereof; inorganic acids such as hydrochloric acid; imidazoles such as imazalil or any antifungal compound known in the art as a preservative for food products, crop protection or after harvest treatment of fruits, vegetables or cereals; ethyl parabenzoate; borax; calcium bisulfite; calcium disodium EDTA; dehydroacetic acid; isothiazoles; and antimicrobials capable of preventing bacterial growth in the composition.
  • weak acid preservatives such as sorbic acid, lactic acid, benzoic acid, propionic acid, citric acid, acetic acid, or an alkali metal or alkali earth metal salt thereof
  • inorganic acids such as hydrochloric acid
  • imidazoles such as imazalil or
  • the invention further provides the presence of a metal salt of a carboxylic acid.
  • the metal which is part of the metal salt of a carboxylic acid is an alkali metal or an alkali earth metal, examples of which are calcium, lithium, magnesium, potassium, or sodium. Practically, good results are obtained when the metal is potassium or sodium.
  • the carboxylic acid comprises from 1 to 7 carbon atoms. Examples are acetic acid, benzoic acid, citric acid, formic acid, lactic acid, propionic acid, sorbic acid but also mixtures thereof. Good examples are carboxylic acids with 3 carbon atoms such as lactic acid and propionic acid and carboxylic acids with 6 carbon atoms such as citric acid and sorbic acid.
  • the stability of natamycin in the composition of the invention is high and the concentration of natamycin remains at high values, also after prolonged periods of time.
  • This effect is the most pronounced where the carboxylic acid is sorbic acid.
  • this effect is most pronounced when the metal is and alkali metal such as potassium.
  • the composition of the invention may also comprise two or more different preservatives.
  • Suitable stabilizers include, but are not limited to, agar, alginic acid, alginate, calcium lactobionate, carrageenan, gellan gum, and guar gum.
  • the composition of the invention may also comprise two or more different stabilizing agents.
  • antioxidants include, but are not limited to, amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazole (e.g. urocanic acid) and derivatives, peptides such as D,L-carnosine, D-carnosine, L-carnosine and derivatives (e.g. anserine), carotenoids, carotenes (e.g. a-carotene, b-carotene, lycopene) and derivatives, chlorogenic acid and derivatives, lipoic acid and derivatives (e.g.
  • amino acids e.g. glycine, histidine, tyrosine, tryptophan
  • imidazole e.g. urocanic acid
  • peptides such as D,L-carnosine, D-carnosine, L-carnosine and derivatives (e.g. anserine)
  • carotenoids e.g.
  • thiols e.g. thioredoxine, glutathione, cysteine, cystine, cystamine and its glycosyl-, N-acetyl-, methyl-, ethyl-, propyl-, amyl-, butyl- and lauryl-, palmitoyl-; oleyl-, y-linoleyl-, cholesteryl- and glycerylester
  • salts thereof dilaurylthiodipropionate, distearylthiodipropionate, thiodipropionic acid and its derivatives (ester, ether, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (such as buthioninsulfoximine, homocysteinesulfoximine, buthioninsul
  • chelators such as a-hydroxy fatty acids, palmic-, phytinic acid, lactoferrin, b-hydroxy acids (such as citric acid, lactic acid, malic acid), huminic acid, gallic acid, gallic extracts, bilirubin, biliverdin, EDTA, EGTA and its derivatives, unsaturated fatty acids and their derivatives (such as y-linoleic acid, linolic acid, oleic acid), folic acid and its derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (such as ascorbyl palmitate and ascorbyl tetraisopalmitate, magnesium ascorbyl phosphate, sodium ascorbyl phosphate, ascorbyl acetate), tocopherol and derivates (such as vitamin E acetate), mixtures of vitamin E, vitamin A and derivatives (vitamin A palmitate and
  • composition of the invention may also comprise two or more different antioxidants.
  • anti-foam forming agents include, but are not limited to, polyethylene glycol 8000, polymethylsiloxane, simethicone octanol, and silicone oils.
  • the composition of the invention may also comprise two or more different anti-foam forming agents.
  • suitable thickening agents include, but are not limited to, agar, alginic acid, alginate, xanthan gum, carrageenan, gellan gum, guar gum, acetylated distarch adipate, acetylated oxidized starch, arabinogalactan, ethyl cellulose, methyl cellulose, locust bean gum, starch sodium octenyl succinate, and triethyl citrate.
  • the composition of the invention may also comprise two or more different thickening agents.
  • suitable fillers include, but are not limited to, montmorillonite, kaolin, veegum, bentonite, and talcum.
  • the composition of the invention may also comprise two or more different fillers.
  • suitable dispersing agents include, but are not limited to, Morwet D-425, Pluronic P, and Silwet L-77.
  • the composition of the invention may also comprise two or more different dispersing agents.
  • Suitable spray oils include, but are not limited to, Banole ® , Banole ® W, Banole ® UBV, SprayTex M, Orchex 692, sunspray 1 1 E.
  • the composition of the invention may also comprise two or more different spray oils.
  • suitable flow additives include, but are not limited to, kaolin, talcum, Wacker- Belsil ® PMS MK, Wacker-Belsil ® TMS 803, magnesium trisilicate, sodium aluminosilicate, bentonite, and polydimethylsiloxane.
  • the composition of the invention may also comprise two or more different flow additives.
  • the composition of the present invention further comprises a diol having a boiling point of between 125°C and 300°C wherein the amount of said diol is from 50 g/kg to 950 g/kg of the total weight of said solution.
  • Suitable diols are diols having a boiling point such as from 125°C to 300°C or having a boiling point of between 150°C and 250°C. Examples are dipropylene glycol, ethylene glycol, polyethylene glycol, propylene glycol or mixtures thereof.
  • natamycin with a metal salt of an organic acid advantageously leads to increase in solubility of natamycin while retaining chemical stability. This is important since a well- known drawback of natamycin is its low solubility. Increase of natamycin concentration may be further positively influenced by the addition of a diol having a boiling point of between 125°C and 300°C.
  • excipients such as thickening agents, stabilizers and/or lubricants may be added.
  • a suitable thickening agent with stabilizing properties in the art is xanthan. Hydroxypropyl cellulose is found to be a suitable excipient as it facilitates film formation leading to better spread of the composition of the invention on fruit or leaves.
  • the present invention relates to use of the composition of the first aspect for the protection of crop against fungal spoilage.
  • Orders of fungi against which the composition of the invention may be applied are Erysiphales or Heliotiales.
  • genus’s that may be combated are Blumeria, Botrytis, Erysiphe, Leveillula, Microsphaera, and Podosphaera.
  • crop treatment with the composition of the invention may be used against Blumeria graminis (powdery mildew in grasses including cereals), Botrytis cinereal (gray mold in strawberry), Erysiphe berberidis (powdery mildew in grape), Erysiphe cichoracearum (powdery mildew in cucurbits), Erysiphe necator (powdery mildew in grape), Leveillula taurica (powdery mildew in onions and artichokes), Microsphaera diffusa (powdery mildew in soybean), Microsphaera syringa (powdery mildew in lilac), Podosphaera aphanis (powdery mildew in strawberry), Podosphaera leucotricha (powdery mildew in apples and pears), or Podosphaera xanthii (powdery mildew in gourds and me
  • composition of the instant invention may be used to combat various plant fungal diseases such as gray mold (caused by Botrytis cinerea) or powdery mildew (caused by species of fungi in the order Erysiphales), for example in strawberry, be it in the open field or in greenhouses.
  • gray mold caused by Botrytis cinerea
  • powdery mildew caused by species of fungi in the order Erysiphales
  • Greenhouse studies show that efficacy of natamycin against powdery mildew increases by the addition of zinc oxide, even up to the level of existing chemical antifungals such as azoxystrobin/difenoconazole and fluxapyroxad/pyraclostrobin.
  • composition of the invention may also be used to prevent mold/fungal growth and/or mold/fungal infection on stored agricultural products such as grain, maize, coffee, beans, cocoa beans, soy beans, berries such as e.g. strawberries, citrus fruits such as e.g. oranges, bananas, pineapples, grapefruits and lemons, grapes, peaches, plums and cherries.
  • stored agricultural products such as grain, maize, coffee, beans, cocoa beans, soy beans, berries such as e.g. strawberries, citrus fruits such as e.g. oranges, bananas, pineapples, grapefruits and lemons, grapes, peaches, plums and cherries.
  • the composition of the invention may also be used during the drying and/or fermentation process of coffee and cocoa beans.
  • composition of the present invention may also be used for the treatment of growing crops in the field including, but not limited to, cereal crops such as grain and maize, vegetables, coffee plants, cocoa plant, fruit trees, grape plants, strawberries, cucumber plants, banana plants, pineapple plants, and tomato plants.
  • cereal crops such as grain and maize, vegetables, coffee plants, cocoa plant, fruit trees, grape plants, strawberries, cucumber plants, banana plants, pineapple plants, and tomato plants.
  • a product that is treated with an effective amount of a composition according to the invention is a further aspect of the present invention.
  • the composition may be present on and/or in the product.
  • the product is normally susceptible to fungal spoilage such as e.g. a food product, feed product, agricultural product, a fabric, a leather, paper, fibers, a paint, and a coating.
  • Food and feed products include, but are not limited to, food and feed products for man or animals.
  • Food or feed product to which the compositions of the invention may typically be applied include, but are not limited to, cheese, cream cheese, shredded cheese, cottage cheese processed cheese, sour cream, dried fermented meat product including salamis and other sausages, wine, beer, yoghurt, juice and other beverages, salad dressing, cottage cheese dressing, dips, bakery products and bakery fillings, surface glazes and icing, spreads, pizza toppings, confectionery and confectionery fillings, olives, olive brine, olive oil, juices, tomato purees and paste, condiments, and fruit pulp and the like food products, as well as feed products, such as pet food, broiler feed fruits, and the like.
  • Agricultural products include, but are not limited to, plants, crops, vegetables and/or fruits. If applied on plants, the composition of the invention can be applied on leaves, the stem, flowers, offshoot of the plants, seeds or cultivars and even on fruits. So, these parts of the plants treated with a composition of the present invention are also included in the present invention.
  • the compositions of the invention may also be applied on bulbs, especially flower bulbs such as tulip, lily, narcissus, crocus or hyacinth; other bulbous crops such as e.g. onions; tubers, root-tubers and rootstocks, such as seed-potatoes and dahlia.
  • compositions of the present invention may be used on cuttings or grafts such as generally applied to multiply flower plants, indoor plants or crops; seeds for growing of new plants and treatment of seeds that are stored as feed or feed (e.g. maize and wheat).
  • cuttings or grafts are carnation, fuchsia, chrysanthemum, roses, fruit plants like tomato, melon, cucumber, and egg-plant and plants grown in greenhouses.
  • the invention relates to a method for treating a product comprising the step of incorporating into the product and/or applying onto the product a composition according to the present invention.
  • the storage life of the product is improved when treated with the composition according to the invention.
  • Treatment of the product with the composition according to the invention prevents mold and/or fungal growth in and/or on the product.
  • the product is an agricultural product.
  • composition of the invention can be applied on plants, crops, vegetables and/or fruits before, during and/or after harvesting.
  • the compositions of the present invention can be applied on fruit like bananas or pineapples or strawberries after harvesting.
  • the composition according to the invention is a liquid which can be applied by dipping, immersion, spraying or electrostatic spraying of products such as agricultural products.
  • the composition may also be added directly in case the substrate is a liquid or semi-liquid.
  • the products can also be treated by brushing using a paintbrush or e.g. by application of a pad of cotton wool or cellulose pads impregnated with the composition of the invention.
  • the composition of the invention can also be applied by using plaster-like carriers.
  • resin-like or wax-like compositions known in the art can be applied.
  • the composition may be applied by means of a coating. Examples of compounds applied as coating are xanthan gum, sugars, glycerides and waxes such as bee-wax. For all these treatments methods and equipment well-known to a person skilled in the art can be used.
  • Another aspect of the invention relates to a method for retaining the antifungal activity of natamycin in a composition upon storage of the composition and/or exposure of the composition to sunlight or ultraviolet light radiation, the method comprising the step of incorporating titanium dioxide or zinc oxide or mixtures thereof into the composition comprising natamycin.
  • Natamycin (0.4 wt.%), xanthan (1 .6 wt.%), potassium sorbate (0.0095 wt.%), propylene glycol (20 wt.%), tween 80 (4 wt.%) and ferulic acid (20.0 wt.%) were mixed with demineralized water in an amount to give the afore-mentioned concentrations.
  • Natamycin (0.4 wt.%), hydroxypropyl cellulose (6 wt.%), potassium sorbate (0.0095 wt.%), propylene glycol (20 wt.%), tween 80 (4 wt.%) and zinc oxide (12 wt.% of a 50 wt.% dispersion) were mixed with demineralized water in an amount to give the afore-mentioned concentrations.
  • Natamycin (0.4 wt.%), xanthan (1 .6 wt.%), potassium sorbate (0.0095 wt.%), propylene glycol (20 wt.%), tween 80 (4 wt.%), methoxy cinnamate (20 wt.%) and octocrylene (20 wt.%) were mixed with demineralized water in an amount to give the afore-mentioned concentrations.
  • natamycin, natamycin/ferulic acid, natamycin/zinc oxide, and natamycin/octocrylene/methoxy cinnamate were determined to inhibit mycelial growth of an isolate of Botrytis cinerea from strawberry by 50% (ECso values) using the spiral gradient dilution method. Amended agar plates were incubated for 3 days at 25°C either in the dark or under light (4300 Lux) before measurement. Solutions as described in Examples 1 -3 were used after 1 :4 dilution with water (i.e. 0.1 wt.% of natamycin).
  • Average ECso values for incubation in the dark were 0.65 pg/ml for natamycin, 0.48 pg/ml for natamycin/ferulic acid, 0.57 pg/ml for natamycin/ zinc oxide, and 0.51 pg/ml for natamycin/octocrylene/methoxy cinnamate. Under light conditions, only natamycin/ zinc oxide resulted in inhibition of growth, and the average ECso value was 6.15 pg/ml. Under the experimental conditions used, the other three formulations of natamycin were apparently degraded to a higher degree and ECso values could not be determined.
  • natamycin/zinc oxide performed significantly better than natamycin alone or natamycin/ferulic acid, and performed similarly well as Switch, reducing the incidence of gray mold to very low levels. Still, natamycin and natamycin/ferulic acid also significantly reduced gray mold as compared to the control. In contrast, for control of natural incidence that occurred at relatively low levels, only natamycin, natamycin/ferulic acid, and Switch resulted in significant reductions from the control on cv. Fronteras, and on cv. Monterey, only Switch was highly effective.
  • Panel A Fruit harvested 1 day after the fourth fungicide application (May 1).
  • Panel B Fruit harvested 7 days after the fourth fungicide application (May 8).
  • natamycin/octocrylene/methoxy cinnamate was compared to natamycin, each applied at 500 pg/ml, and to the industry standard Switch (fludioxonil + cyprodinil) at 14 oz/A.
  • Switch fludioxonil + cyprodinil
  • Fruits were harvested 1 day after the 3rd application and 7 days after the 4th application. Calyx browning, and leaf necrosis were prominent on fruit treated with natamycin/octocrylene/methoxy cinnamate, and an oily residue was noted on fruit.
  • natamycin/octocrylene/methoxy cinnamate was more effective than natamycin and was numerically the most effective treatment on both cultivars; on Fronteras it was significantly more effective than Switch (see below Table, panel B).
  • the natural incidence of gray mold was again effectively and significantly reduced in comparison to the control on both cultivars only by Switch.
  • Panel B Fruit harvested 7 days after the fourth fungicide application (May 29).
  • natamycin/zinc oxide was determined to be the best candidate.
  • Natamycin/ferulic acid and natamycin/octocrylene/methoxy cinnamate showed phytoxicity on plants and fruit calyxes, so they were deemed non-viable for commercial use.
  • natamycin at 500 pg/ml was mixed with two rates of zinc oxide (0.5% or 1 %), and efficacy was compared to natamycin itself and Switch. Two applications with each of these treatments were done on June 4 and June 8 (2016) before harvest. Zinc oxide at 1 % left visible residues on treated plants, whereas this was much less obvious when using zinc oxide at 0.5%.
  • the three natamycin treatments performed equally well, and the incidence of gray mold was significantly lower as compared to the untreated control and to Switch (see below Table, panel A).
  • natamycin- 1 % zinc oxide The natural incidence of decay was significantly reduced from the control by natamycin- 1 % zinc oxide and by Switch on cv. Fronteras and by natamycin-0.5% zinc oxide and Switch on cv. Monterey.
  • the addition of zinc oxide increased natamycin efficacy against natural incidence of gray mold.
  • natamycin and natamycin-1 % zinc oxide performed equally well on cv. Fronteras and were significantly more effective than Switch (see below Table, panel B).
  • natamycin-1 % zinc oxide resulted in numerally the lowest incidence of gray mold, but there was no significant difference to the other two natamycin treatments.
  • Panel A Fruit harvested 1 day after the second fungicide application (June 8).
  • Panel B Fruit harvested 7 days after the second fungicide application (June 14).
  • the treatments were as follows 1) Untreated control; 2) Quadris Top (difenoconazole + azoxystrobin, 14 fl. oz/A); 3) Merivon (fluxapyroxad + pyraclostrobin 1 1 fl. oz/A); 4) natamycin (1000 pg/ml); 5) natamycin (1000 pg/ml) + zinc oxide (1 %). Leaves were sprayed on both sides to run-off using a hand spray bottle.

Abstract

La présente invention concerne une composition comprenant de la natamycine et de l'oxyde de zinc pour protéger une culture contre une infection fongique.
PCT/EP2020/058478 2019-03-28 2020-03-26 Protection de culture contre une infection fongique WO2020193679A1 (fr)

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WO2017216722A2 (fr) 2016-06-13 2017-12-21 Vyome Biosciences Pvt. Ltd. Compositions antifongiques synergiques et leurs procédés
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WO2002081717A2 (fr) 2001-04-06 2002-10-17 Asa Spezialenzyme Gmbh Production de pimaricine et de derives de pimaricine et leur utilisation pour la protection phytosanitaire
WO2004105491A1 (fr) 2003-06-02 2004-12-09 Dsm Ip Assets B.V. Solution aqueuse stable d'un fongicide a base de natamycine
WO2005074687A1 (fr) 2004-02-05 2005-08-18 Dsm Ip Assets B.V. Antibiotique polyenique pour le controle de la proliferation fongique dans les cultures de bananes
WO2010094670A1 (fr) * 2009-02-17 2010-08-26 Dsm Ip Assets B.V. Compositions antifongiques de polyène
WO2017043972A1 (fr) * 2015-09-09 2017-03-16 Arec Crop Protection B.V. Composition antifongique comprenant de la natamycine et des acides gras c4-c22, des monoglycérides de ces acides gras et/ou des dérivés de ces acides gras
WO2017216722A2 (fr) 2016-06-13 2017-12-21 Vyome Biosciences Pvt. Ltd. Compositions antifongiques synergiques et leurs procédés
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