WO2018102345A1 - Utilisation de l'auréobasidine antifongique en agriculture - Google Patents

Utilisation de l'auréobasidine antifongique en agriculture Download PDF

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Publication number
WO2018102345A1
WO2018102345A1 PCT/US2017/063599 US2017063599W WO2018102345A1 WO 2018102345 A1 WO2018102345 A1 WO 2018102345A1 US 2017063599 W US2017063599 W US 2017063599W WO 2018102345 A1 WO2018102345 A1 WO 2018102345A1
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WO
WIPO (PCT)
Prior art keywords
infection
agricultural product
aureobasidin
composition according
agricultural
Prior art date
Application number
PCT/US2017/063599
Other languages
English (en)
Inventor
Jon D. Polishook
Daniel P. RING
Sheo B. Singh
James Frederic Walter
Original Assignee
Agrobiologics Llc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Application filed by Agrobiologics Llc filed Critical Agrobiologics Llc
Publication of WO2018102345A1 publication Critical patent/WO2018102345A1/fr

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Classifications

    • 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
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • 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
    • A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
    • A01N63/30—Microbial fungi; Substances produced thereby or obtained therefrom

Definitions

  • the present invention is concerned with the use of the natural product aureobasidin A (AbA) as an agricultural fungicide.
  • the invention is also concerned with compositions comprising aureobasidin A (AbA), their preparation, and methods of using such compositions to control agricultural pests including, but not limited to, fungi selected from the group consisting of Magnaporthe oryzae, Alternaria solani, Septoria triticum, Fusarium oxysporum, and Rhizoctonia solani.
  • Aureobasidin A-R are antifungal cyclic depsipeptide antibiotics produced by Aureobasidium pullulans (Takesako et al, Journal of Antibiotics, 1991, 44, 919-924).
  • Aureobasidin A is the most prominent, potent and studied member of this class of depsipeptides (Takesako et al, Journal of Antibiotics, 1991, 44, 919-924; Ikai et al, Journal of Antibiotics, 1991, 44, 925-933; and Takesako et al, Journal of Antibiotics, 1993, 46, 1414-1420). It was shown to have excellent activity against Candida, Aspergillus and Cryptococcus (U.S. Patent No. 5,698,670; Takesako et al, Journal of Antibiotics, 1993, 46, 1414-1420).
  • AbA targets the inositol phophorylceramide (IPC) synthase, a key enzyme catalyzing sphingolipid synthesis in fungi (Cerantola et al., Molecular Microbiology 2009, 71, 1523-1537) but which is absent in mammals.
  • IPC inositol phophorylceramide
  • Magnaporthe oryzae is a hemibiotrophic fungal pathogen that causes rice (Oryza sativa) blast, the most damaging disease on rice.
  • Alternaria solani is a fungal pathogen that produces a disease in tomato and potato plants called early blight that is extremely destructive.
  • Septoria tritici blotch (STB) caused by the ascomycete fungus Mycosphaerella graminicola (asexual stage: Septoria tritici), is one of the most important foliar diseases of wheat. Fusarium oxysporum is a pathogenic fungus common in soils around the world, and the cause of fusarium wilt, a deadly vascular wilting syndrome in plants.
  • Fusarium oxysporum comprises over 120 known strains or "special forms" (formae speciales; f. sp.), each of which is specific to a unique plant host in which it causes disease.
  • special forms formae speciales; f. sp.
  • These F. oxysporum strains infect and kill a large host range including many commercially harvested crops such as species in the Solenaceae family (tomatoes, peppers, potatoes, eggplant), watermelon, lettuce, legumes, beets, basil, strawberries, chrysanthemum, sugarcane, bananas, and multiple other species.
  • Rhizoctonia solani causes a wide range of commercially significant plant diseases.
  • Brown patch a turfgrass disease
  • damping off e.g., in soybean seedlings
  • black scurf of potatoes bare patch of cereals
  • root rot of sugar beets a turfgrass disease
  • belly rot of cucumber a turfgrass disease
  • sheath blight of rice a turfgrass disease
  • aureobasidin A is useful as an agricultural fungicide to treat, prevent, or control fungal infections in agricultural products, such as plants and seeds. Plants will include fruits and vegetables.
  • aureobasidin A has been found to be effective in treating, preventing, or controlling infections in agricultural products caused by the following fungi: Magnaporthe oryzae, Alternaria solani, Septoria triticum, Fusarium
  • a second aspect of the present invention is concerned with agricultural compositions of aureobasidin A comprising an effective amount of the antifungal compound and an agriculturally acceptable carrier.
  • Such compositions may additionally comprise one or more excipients selected from the group consisting of (a) one or more diluents, (b) one or more binders or binding agents, (c) one or more dispersing agents, (d) one or more emulsifying agents, (e) one or more surfactants or wetting agents, (f) one or more sticking agents, (g) one or more thickening agents, and (h) a pH adjuster.
  • the surfactant is an anionic surfactant.
  • the surfactant is a non-ionic surfactant.
  • Aureobasidin A and agricultural compositions of aureobasidin A of the present invention may also be used in combination with one or more other agents useful to treat, prevent, or control agricultural pests in the field.
  • the compositions of the present invention and other active agents may be administered separately or in conjunction.
  • the administration of one element may be prior to, concurrent to, or subsequent to the
  • compositions of the present invention examples include, but are not limited to:
  • antifungal agents such as Ilicicolin H, azoxystrobin and myclobutanil;
  • plant growth regulators such as dikegulac-sodium and trinexapac-ethyl
  • herbicides such as prodiamine and glyphosate
  • insecticides such as bifenthrin and malathion
  • acaricides such as avermectin and kelthane.
  • the agricultural compositions of the present invention may contain about 0.1 to 95 percent by weight of aureobasidin A.
  • compositions of aureobasidin A may be applied using a variety of methodologies, including soil drench, seed treatment, granular and foliar spray. With regard to the treatment of seeds, the compositions may alternatively be applied directly to the seed before planting of the seed or applied to the locus or soil in which the seeds are sown prior to the planting of the seed.
  • the concentration of aureobasidin A to be applied to the agricultural product is about 0.001 to 1 percent by weight. In a class of this method the concentration of aureobasidin A to be applied to the agricultural product is about 0.001 to 0.01 percent by weight.
  • Another aspect of the present invention relates to the total amount of aureobasidin A to be applied per area of the field.
  • about 2 to about 1000 grams of aureobasidin A are to be applied per acre.
  • about 5 to 500 grams of aureobasidin A are to be applied per acre.
  • about 0.025 kilograms to about 5 kilograms of aureobasidin A are to be applied per hectare.
  • about 0.05 kilograms to about 1 kilogram of aureobasidin A are to be applied per hectare.
  • Another aspect of the present invention relates to the use of aureobasidin A and the compositions of the present invention to treat, control, or prevent fungal infections on an agricultural product.
  • the present invention also relates to a food, feed, or agricultural product treated with a composition of the present invention.
  • the present invention also relates to a process for the treatment of an agricultural product which comprises applying a composition of the present invention to such agricultural product or plant.
  • the present invention also relates to the use of a fermentation broth derived from strains of Aureobasidium pullulans as a live cell or cell suspension to treat, control, or prevent a fungal infection on an agricultural product.
  • Such fermentation broths contain the antifungal agent aureobasidin A, which need not be isolated, purified, and re-formulated for use as an agricultural fungicide.
  • the present invention is concerned with the use of the naturally occurring antifungal aureobasisin A (AbA) to control the growth of agricultural pests including, but not limited to, Magnaporthe oryzae, Alternaria solani, Septoria triticum, Fusarium Oxysporum, and Rhizoctonia solani.
  • ABSA antifungal aureobasisin A
  • Aureobasidin A can be used to control a variety of plant diseases and can be applied in a variety of methodologies, including soil drench, seed treatment, granular and foliar spray. It can be readily formulated into a variety of compositions, including, but not limited to, emulsifiable concentrates, inverse emulsions, microemulsions, dispersible granules, wettable powders, dusts, and granules.
  • Aureobasidin A offers several advantages over existing synthetic fungicides. Since it is derived from natural sources, it already occurs in the environment and biological processes to degrade the compound are already present in the environment. Unlike many conventional fungicides, aureobasidin A does not contain any heavy metals or halogens and therefore is totally biologically degradable. Moreover, aureobasidin A has a different mechanism of action from existing commercial fungicides and therefore can be used to reduce fungicide resistance found in certain plant diseases.
  • agricultural product as used herein is to be understood in a very broad sense and includes, but is not limited to, cereals, e.g., wheat, barley, rye, oats, rice, sorghum, and the like; beets, e.g. sugar beet and fodder beet; pome and stone fruit and berries, e.g. apples, pears, plums, apricots, peaches, almonds, cherries, strawberries, raspberries and blackberries; leguminous plants, e.g. beans, lentils, peas, and soybeans; oleaginous plants, e.g.
  • rape mustard, poppy, olive, sunflower, coconut, castor-oil plant, cocoa, and ground-nuts
  • cucurbitaceae e.g. pumpkins, gherkins, melons, cucumbers, squashes, and aubergines
  • fibrous plants e.g. cotton, flax, hemp, and jute
  • citrus fruit e.g. oranges, lemons, grapefruits, mandarins, and limes
  • tropical fruit e.g. papayas, passion fruit, mangos, carambolas, pineapples, bananas, and kiwis
  • vegetables e.g. spinach, lettuce, asparagus
  • brassicaceae such as cabbage and turnips, carrots, onions, tomatoes, potatoes, seed potatoes, hot and sweet peppers
  • laurel-like plants e.g. avocado, cinnamon, camphor tree
  • products such as maize, tobacco, nuts, coffee, sugarcane, tea, grapevines, hops, rubber plants, as well as ornamental plants, e.g.
  • cut flowers roses, tulips, lilies, Narcissus, crocuses, hyacinths, dahlias, Gerbia, carnations, fuchsias, chrysanthemums, and flower bulbs, shrubs, deciduous trees and evergreen trees such as conifers, plants and trees in greenhouses. It includes, but is not limited to, plants and their parts, fruits, seeds, cuttings, cultivars, grafts, bulbs, tubers, root-tubers, rootstocks, cut flowers and vegetables.
  • Aureobasidium pullulans is grown and cultivated as described in Takesako et al., "Aureobasidins, New antifungal antibiotics taxonomy, fermentation, isolation and properties" Journal of Antibiotics 1991, 44, 919-924.
  • Aureobasidium pullulans is inoculated in 100 mL of liquid medium composed of yeast nitrogen base (Difco) 0.67% and glucose (2%) in a 500 mL Erlenmeyer flask. The flask is shaken at 25°C for two days to give a seed culture.
  • One-liter seed culture is transferred into 200-liter fermenter containing 100 liters of medium consisting of glucose 2%, ammonium sulfate 0.5%, potassium hydrogen phosphate sodium chloride 0.01%, microgram/mL, and microgram/mL. Twenty liters of a medium containing glucose 10%, ammonium sulfate 2.5%, polypepton 5%, potassium hydrogen phosphate sodium chloride
  • microgram/mL, and microgram/mL is supplemented to the culture.
  • the fermentation is further continued at 25°C for 78 hours with 120-liters/minute aeration and 100 rpm agitation.
  • the fermentation broth from producer strains can be processed in several different ways depending on the utility. In one method, the mycelia are separated and extracted by ethanol, methanol, acetone or ethyl acetate. The extract is concentrated and aureobasidin A is purified by standard chromatographic methods as described by Takesako et al, Journal of Antibiotics, 1991, 44, 919-924. In a second method, the fermentation broth is lyophilized to remove water to afford a dry powder.
  • the cells in the fermentation broth are broken if necessary by addition of organic solvent, such as methanol, ethanol, acetone, and the like, and then evaporated to dryness to afford a powder.
  • organic solvent such as methanol, ethanol, acetone, and the like
  • the fermentation broth obtained directly or after breaking the cells with solvent is sprayed onto the plant by foliar treatment, mixed with seeds, or used as a soil inoculant.
  • broth powders generated using either of the two methods is mixed with appropriate agent(s) and sprayed by foliar treatment, mixed with seeds, or used as a soil inoculant.

Abstract

La présente invention concerne l'utilisation du produit naturel de l'auréobasidine A (AbA) en tant que fongicide agricole, des compositions comprenant de l'auréobasidine A, et l'utilisation de telles compositions pour traiter, contrôler ou prévenir une infection fongique dans des produits agricoles, en particulier, les champignons étant choisis dans le groupe constitué de Magnaporthe oryzae, Alternaria solani, Septoria triticum, Fusarium oxysporum, et Rhizoctonia solani.
PCT/US2017/063599 2016-11-30 2017-11-29 Utilisation de l'auréobasidine antifongique en agriculture WO2018102345A1 (fr)

Applications Claiming Priority (2)

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US201662427855P 2016-11-30 2016-11-30
US62/427,855 2016-11-30

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WO2018102345A1 true WO2018102345A1 (fr) 2018-06-07

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110183521A (zh) * 2019-05-23 2019-08-30 华南农业大学 稻瘟菌基因MoRMD1在调控稻瘟菌致病力中的应用
WO2021245100A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245104A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245105A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245103A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245102A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245106A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2023089007A1 (fr) 2021-11-19 2023-05-25 Syngenta Crop Protection Ag Compositions fongicides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0500264A1 (fr) * 1991-02-19 1992-08-26 Takara Shuzo Co. Ltd. Fongicides agricoles et horticoles
EP0670166A2 (fr) * 1994-03-01 1995-09-06 Eli Lilly And Company Compositions pharmaceutiques administrables par voie buccale
US20140024578A1 (en) * 2011-04-01 2014-01-23 AureoGen Biosciences ,Inc. Aureobasidin derivatives and methods of synthesis

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0500264A1 (fr) * 1991-02-19 1992-08-26 Takara Shuzo Co. Ltd. Fongicides agricoles et horticoles
EP0670166A2 (fr) * 1994-03-01 1995-09-06 Eli Lilly And Company Compositions pharmaceutiques administrables par voie buccale
US20140024578A1 (en) * 2011-04-01 2014-01-23 AureoGen Biosciences ,Inc. Aureobasidin derivatives and methods of synthesis

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LIU ET AL.: "In vitro inhibition of postharvest pathogens of fruit and control of gray mold of strawberry and green mold of citrus by aureobasidin A.", INTERNATIONAL JOURNAL OF FOOD MICROBIOLOGY, vol. 119, no. 3, November 2007 (2007-11-01), pages 223 - 229, XP022336528 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110183521A (zh) * 2019-05-23 2019-08-30 华南农业大学 稻瘟菌基因MoRMD1在调控稻瘟菌致病力中的应用
WO2021245100A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245104A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245105A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245103A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245102A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2021245106A1 (fr) 2020-06-04 2021-12-09 Syngenta Crop Protection Ag Compositions fongicides
WO2023089007A1 (fr) 2021-11-19 2023-05-25 Syngenta Crop Protection Ag Compositions fongicides

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