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WO1993001720A1 - Traitement a la natamycine de grains de cereales complets seches - Google Patents

Traitement a la natamycine de grains de cereales complets seches Download PDF

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Publication number
WO1993001720A1
WO1993001720A1 PCT/US1992/005792 US9205792W WO9301720A1 WO 1993001720 A1 WO1993001720 A1 WO 1993001720A1 US 9205792 W US9205792 W US 9205792W WO 9301720 A1 WO9301720 A1 WO 9301720A1
Authority
WO
WIPO (PCT)
Prior art keywords
grain
polyene
natamycin
fungi
whole kernel
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US1992/005792
Other languages
English (en)
Inventor
Bruce Dexter King
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Conagra Brands Inc
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Conagra Inc
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.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co, Conagra Inc filed Critical EI Du Pont de Nemours and Co
Priority to CA002114102A priority Critical patent/CA2114102C/fr
Publication of WO1993001720A1 publication Critical patent/WO1993001720A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B9/00—Preservation of edible seeds, e.g. cereals
    • A23B9/16—Preserving with chemicals
    • A23B9/24—Preserving with chemicals in the form of liquids or solids
    • A23B9/26—Organic compounds; Microorganisms; Enzymes
    • A23B9/28—Microorganisms; Enzymes ; Antibiotics
    • 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
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K30/00—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs
    • A23K30/10—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs of green fodder
    • A23K30/15—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs of green fodder using chemicals or microorganisms for ensilaging

Definitions

  • the invention relates to a process for treating dried whole kernel grains with natamycin to control and/or prevent the growth of yeasts, molds and other fungi. It is desirable to store whole driedkernel grain under conditions of minimal microorganism attack, with its attendant formation of toxins. Fungi attack is particularly troublesome because of the high propensity of fungi to attack grain and the toxic nature of mycotoxins that certain fungi may generate. Perhaps the most prevalent and mycotoxin-producing organisms that attack grain are molds; particularly Fusarium, Penicillium andAspergillus molds.
  • Silo storage has not been wholly successful in long term grain or ensilage storage where mycotoxin production must be limited.
  • the conventional practice of ensiling is the storage of high moisture content fodder which is fermented to increase the acidity of the fodder wherein the acidity controls but does not prevent the formation of significant quantities of toxins (i.e., toxins which are released by the metabolic activities of certain fungi). Fermentation has the disadvantage in that it decreases the food nutrient value of the stored fodder.
  • the use of antibiotics to control organism growth on ensilage stored in a silo is not generally practiced because relatively high concentrations of antibiotics normally would be required for the prolonged periods associated with the conventional high moisture environment of silo storage.
  • Natamycin is known generally to be useful as an antifungal agent.
  • Natamycin is a member of the polyene family of antimycotics. This family is characterized by a macrolide ring of carbon atoms closed by lactonization and possesses a series of conjugated double bonds. Members of this family can be classified by the number of double bonds and whether or ' not the compound contains a glycosidically linked carbohydrate.
  • the compound natamycin is a tetraene with a molecular weight of about 666, an empirical formula corresponding generally to C33H47NO13, and contains a glycosidically-linked carbohydrate moiety, mycosamine. Natamycin has an isoelectric point of pH 6.5. The structure of natamycin exists in two configurations: the enol-structure and the keto- structure.
  • the invention relates to a process for treating grain with a polyene to reduce the damage associated with a fungi attack.
  • the present invention is intended to encompass using any member of the polyene family which is effective in controlling and/or reducing fungal contamination during storage of the dried whole kernel grain.
  • the present invention relates to a process and a product produced thereby which is obtained by using a polyene antibiotic, particuraUy natamycin, to control and/or protect dried whole kernal grain from fungi contamination.
  • the invention also controls and/or prevents contamination of the whole kernal grain from mycotoxins which may be released by the fungi.
  • the invention permits dried whole kernal grain to be stored for prolonged periods of time while remaining substantially free from fungal contamination.
  • the polyene may be sprayed, admixed, etc., with the dried whole kernal grain by any technique which is adequate to provide the polyene to the whole kernal grain in an effective manner.
  • the present invention relates to the treatment of stored dried whole kernel grain with small quantities of an antibiotic from the polyene family, such as natamycin.
  • an antibiotic from the polyene family such as natamycin.
  • the presence of a polyene inhibits fungi attack such as the growth of fungi, mold, yeast, etc., and possible resultant mycotoxin contamination.
  • the invention also permits grain to be stored for longer periods of time and improves the quality of the grain which is eventually removed from storage (e.g., the removed grain is substantially free of fungal contamination).
  • polyene antibiotic defines and refers to one or more members of the recognized class of antibiotics, released by fermentation of a species of the Streptomyces genus, that are particularly effective against fungi. Also encompassed are the equivalent polyene derivates, such as esters, salts, and the like. Further, other pharmaceutically acceptable derivatives of natamycin may used to practice the invention which are effective to control and/or prevent contamination by the fungi.
  • the preferred polyene for use in the present invention comprises natamycin because natamycin will typically give prolonged antifungal protection at a relatively low non-toxic dosage, and accordingly, natamycm is economical for prolonged grain storage.
  • Bioly effective amount defines that the polyene antibiotic is present in a sufficient quantity and will remain active for a time sufficient to give adequate antifungal control for the contemplated usage of the stored grain; that is control to adequately preserve the grain against fungi, mold, yeast, etc., growth and mycotoxin contamination over the entire storage period.
  • Gram defines and refers to one or more species of grain that is to be stored dry for a prolonged time, such as from harvest until spring, for seed grain, or from harvest to harvest for continuous cereal manufacture. Particularly contemplated are monocots grains for use in human food products and animal feed such as cereal grains, seeds, etc., including corn, popcorn, oats, barley, rice, rye, wheat, grass seeds, canola and sunflower seeds, soy beans, etc.
  • “Whole kernel” grain defines and refers to grain that has not been substantially crushed or otherwise fractured, and that has its hull generally intact encompassing the grain.
  • whole kernal grain defines and includes grains, such as corn, that is on its growth substrate such as a corn cob, and/or individual kernels. However, this term does not include grain, such as many conventional animal feeds (e.g., poultry feed), where the individual kernels have been crushed or fractured to break open the protective kernel hulls.
  • Storage defines any technique whereby the grain is kept in its dried whole kernel form for a prolonged period of time, namely 1 to 2 weeks, months or more. Storage may be in elevators, bins, bags, etc. An important aspect of the invention is that the storage is for the purpose of substantially retaining the grain in its initial as-stored condition, without significant change or contamination by microorganism attack.
  • “Dried” defines that the grain, either sun dried or heat dried, has had its initial moisture content of at least about 30% by weight decreased to about 15% or lower, normally about 7%.
  • Non-toxic defines the concentration of the polyene and substances used therewith in accordance with the invention for effective biological protection of the grain. Non-toxic does not include unacceptable quantities of either toxic chemicals from the polyene or mycotoxins from fungi infestation.
  • the polyene e.g.,natamycin
  • the polyene is useful at quantities of only about 5g through at least about 50g per ton, at which quantities it is biologically effective in controlling fungi attack or infestation while being non-toxic in food products (e.g.,animal feed), which are to be ingested by animals and/or humans.
  • Concentrations of natamycin of about 5.5 ppm through at least about 55 ppm based on the weight of the dried grain to be treated are non-toxic and biologically effective, for protecting the grain for 2 months or longer against significant fungal infestation and/or mycotoxin contaimnation.
  • the exact dosage which is sufficient to be effective against the fungi is dependent upon the specific storage conditions.
  • the storage conditions are favorable for the metabolic activities of the fungi, a relatively large amount of the polyene will be required.
  • Storage conditions which are warm, moist, possesses a neutral pH, contain oxygen, include a metabolizable substrate, etc. would require a relatively large dosage of the polyene to be effective against the attacking fungi.
  • the amount of the polyene which is necessary to prevent growth and/or possible toxin contamination by the fungi is less than the amount which is necessary to treat an existing fungal outbreak. Therefore, it is advantageous to treat the whole kernel grain immediately after drying.
  • the fungi tend to attack any imperfection in the whole kernel grain which permits the fungi to penetrate into the internal regions of the kernel (e.g., the interior of the kernel contains starches and sugars which may be consumed by the fungi).
  • the kernel may be damaged during drying, transport, etc., in a manner that renders the kernel susceptible to attack by a fungi.
  • the dried whole kernel may contain or develop a crack in the hull which is sufficient to permit entry of the fungi.
  • the eye of the kernel is especially susceptible to damage and consequently attack by fungi even though the hull may not be cracked. Should the fungal attack of stored grain be extensive it may be necessary to dispose of the entire contents of a storage vessel (e.g., the presence of fungi and toxins thereof may render all of the kernels of grain in an elevator unsuitable for any purpose).
  • the preferred morphology of the polyene is crystalline; however, any morphological state is acceptable in practice of the invention which is effective against the fungi.
  • the polyene used in the invention may be present in one or more hydrate forms (e.g., mono-, and tri-hydrates).
  • the tri-hydrate form is advantageous in some aspects of the invention due to its stability.
  • Natamycin is an acceptable polyene for practicing the present invention which per se is essentially insoluble in water. Certain non-toxic biologically equivalent derivatives of natamycin may be water soluble. Natamycin and/or a water-soluble biologically equivalent derivative can be supplied to the grain in any convenient way which provides the desired polyene to the dried whole kernels in a manner sufficient to be biologically effective against the fungi.
  • the polyene(s) can be applied (e.g.,sprayed, admixed, coated, etc.), onto the grain as an aerosol, a fog, mist, powder, aqueous suspension, solution, etc. Excessive wetting of the dried. grain is to be avoided (e.g., moisture enhances the growth rate of the attacking fungi).
  • the polyene is supplied while the grain is being delivered or transported to the storage facility, such as when it is being conveyed into an elevator, bin, bag, etc. Care must be taken to achieve a polyene application that is distributed (e.g., uniformly), and remains throughout the grain during storage.
  • the polyene is suspended within a non-toxic carrier liquid and sprayed upon the dried whole kernel grain.
  • the carrier liquid should generally not be a solvent for the polyene.
  • certain biologically effective and/or pharmaceutically acceptable derivatives of the polyene which may be soluble within the non-toxic carrier liquid may be used alone and/or in conjunction with natamycin to practice the invention.
  • Suitable non-toxic carrier liquids comprise at least one member of the following group: alcohols such as methanol, w,ater, etc.
  • the polyene may be comminuted or ground into a powder to increase its surface area.
  • the increased surface area may enhance the effectiveness and ability of the polyene to be distributed uniformly throughout the dried whole kernel grain (e.g., relatively small particles of natamycin may be readily directly admixed with whole kernal grain for storage).
  • the length of protected storage is relatively independent of the treatment concentration. For example, if an amount of natamycin is applied to the whole kernal grain that will give adequate antifungal protection to the grain stored in a dark and dry environment for about 2 months, it normally is not necessary to increase the amount of natamycin to be used even for significantly longer storage times (e.g., from harvest to harvest). For example, it would be expected that a suspension comprising natamycin, a non-toxic carrier liquid and a wetting agent which is sprayed onto grain, that is to be stored in a dark and dry environment for at least about 2 weeks, is effective to reduce if not prevent any fungal attack. This, of course, is premised on the natamycin being chemically stable under the conditions of storage.
  • the polyene suspension discussed above may include other substances such that a plurality of dried grain treatments may be implemented simultaneously.
  • the polyene treatment of the invention does not preclude using the treated whole kernel grain in any subsequent process or end product (e.g., whole kernels of grain treated in accordance with the invention may be removed from storage and processed subsequently into flakes, grist, etc.). While not wishing to be bound by any theory or explanation, it is believed that the polyene is active or effective against the fungi, but not against bacteria. One explanation may be that fungi (but not bacteria) contain ergosterol in their membranes.
  • the fungi will grow, if the environment is appropriate, until contacting the natamycin.
  • the theorized mechanism of the polyene action is a binding of the polyene molecule and ergosterol present in the cell membrane of the fungi, mold, yeast, etc.
  • the complexing with ergosterol is substantiated by the neutralizing effects of ergosterol addition on the antifungal activities of the polyene against the fungi.
  • a complex between the polyene and the cell membrane of the fungi is believed to alter membrane permeability since the polyene is a relatively large molecule which creates an increased surface pressure which may tend to induce a reorientation of the ergosterol present in the membrane, thus altering permeability of the cell and resulting in osmotic shock.
  • This osmotic shock is typically sufficient to interrupt, if not halt, the metabolic activities of the fungi (e.g., the polyene may cause irregular fungi growth, sporulation, etc.).
  • a significant aspect of this invention is that very small amounts of a polyene such as natamycin are effective in preventing the excessive contamination of the whole kernel grain by mycotoxins during storage. This is of particular importance where the grain is to be used in food products, particularly in human food products such as cereal, where the polyene compound must be compatible with consumption by the human and/or animal.
  • the polyenes used in accordance with the invention are non-toxic to humans and animals. Generally any polyene which is consumed by an animal (e.g., cattle, poultry, swine, etc.) is normally not retained within the flesh of the animal. As a result, the polyene does not adversely affect human consumption of any animal which has consumed a feed containing the polyene.
  • one aspect of the invention permits controlling and/or preventing fungal attack to whole kernel grain which may be fed to animals such that any processed animal is not contaminated with fungi, toxins thereof and/or antifungal agents.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Polymers & Plastics (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Food Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Environmental Sciences (AREA)
  • Animal Husbandry (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Beans For Foods Or Fodder (AREA)
  • Catching Or Destruction (AREA)
  • Fodder In General (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)

Abstract

Des antibiotiques au polyène, en particulier la natamycine, sont utilisés pour protéger des grains de céréales complets séchés contre la croissance de moisissures et contre toute contamination associée par des mycotoxines.
PCT/US1992/005792 1991-07-25 1992-07-10 Traitement a la natamycine de grains de cereales complets seches Ceased WO1993001720A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002114102A CA2114102C (fr) 1991-07-25 1992-07-10 Traitement de grains entiers seches par la natamycine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US73597791A 1991-07-25 1991-07-25
US735,977 1991-07-25

Publications (1)

Publication Number Publication Date
WO1993001720A1 true WO1993001720A1 (fr) 1993-02-04

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ID=24957962

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1992/005792 Ceased WO1993001720A1 (fr) 1991-07-25 1992-07-10 Traitement a la natamycine de grains de cereales complets seches

Country Status (6)

Country Link
JP (1) JP2714483B2 (fr)
CN (1) CN1068704A (fr)
AU (1) AU2397792A (fr)
CA (1) CA2114102C (fr)
MX (1) MX9204345A (fr)
WO (1) WO1993001720A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995014395A1 (fr) * 1992-01-28 1995-06-01 Ducoa L.P. Compositions d'alimentation pour le betail a base de biomasse antibiotique
US5902579A (en) * 1991-08-05 1999-05-11 Bio-Technical Resources Natamycin-containing streptomyces biomass and its use in animal feed
EP1068809A3 (fr) * 1999-07-16 2002-01-02 International Fiber Corporation Composition anti-mycotique
WO2002081717A3 (fr) * 2001-04-06 2002-12-12 Asa Spezialenzyme Gmbh Production de pimaricine et de derives de pimaricine et leur utilisation pour la protection phytosanitaire
WO2007039572A1 (fr) * 2005-10-04 2007-04-12 Dsm Ip Assets B.V. Préparation antifongique améliorée
WO2014085565A1 (fr) * 2012-11-29 2014-06-05 Bayer Cropscience Lp Procédés de contrôle de pathogènes fongiques à l'aide de fongicides polyène
WO2014191449A1 (fr) * 2013-05-31 2014-12-04 Dsm Ip Assets B.V. Agriculture microbienne
WO2014191450A1 (fr) * 2013-05-31 2014-12-04 Dsm Ip Assets B.V. Agriculture microbienne

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MXPA05010103A (es) * 2003-03-21 2005-11-23 Dsm Ip Assets Bv Solucion acuosa estable de un polieno funguicida.
CN105219819A (zh) * 2015-09-29 2016-01-06 山东西王糖业有限公司 一种控制微生物染菌的淀粉及淀粉糖生产工艺

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3892850A (en) * 1956-03-13 1975-07-01 Gist Brocades Nv Pimaricin and process of producing same
DE2530903A1 (de) * 1974-07-10 1976-01-29 Procida Verwendung von gegenueber fungi wirksamen substanzen zum schutz von samen
GB1470005A (en) * 1974-07-03 1977-04-14 Gist Brocades Nv Anti-fungal preparations
US4536494A (en) * 1983-11-17 1985-08-20 Carter A Franklin Animal feed method employing natamycin
US4600706A (en) * 1983-11-17 1986-07-15 Carter A F Anti-fungal feed compositions containing natamycin

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5443057B2 (ja) 2009-05-29 2014-03-19 オルガノ株式会社 嫌気性生物処理方法及び嫌気性生物処理装置

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3892850A (en) * 1956-03-13 1975-07-01 Gist Brocades Nv Pimaricin and process of producing same
GB1470005A (en) * 1974-07-03 1977-04-14 Gist Brocades Nv Anti-fungal preparations
DE2530903A1 (de) * 1974-07-10 1976-01-29 Procida Verwendung von gegenueber fungi wirksamen substanzen zum schutz von samen
US4536494A (en) * 1983-11-17 1985-08-20 Carter A Franklin Animal feed method employing natamycin
US4600706A (en) * 1983-11-17 1986-07-15 Carter A F Anti-fungal feed compositions containing natamycin

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
R. Wegler"Chemie der Pflanzenschutz-und Sch{dlings-bek{mpfungsmittel", 1981, Springer-Verlag,, *
STN International, File CABA, STN accession no. 91:90066, D'Urso, G. et al.: "Effects of adding Na-bentonite, formic acid and pimaricin on the fermentation characteristics and aerobic deteri- oration of triticale silage", & Zootecnica e Nutri- zione Animale, (1990) 16(2) 99-106 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5902579A (en) * 1991-08-05 1999-05-11 Bio-Technical Resources Natamycin-containing streptomyces biomass and its use in animal feed
WO1995014395A1 (fr) * 1992-01-28 1995-06-01 Ducoa L.P. Compositions d'alimentation pour le betail a base de biomasse antibiotique
EP1068809A3 (fr) * 1999-07-16 2002-01-02 International Fiber Corporation Composition anti-mycotique
US6576617B2 (en) 1999-07-16 2003-06-10 International Fiber Corporation Direct action anti-mycotic
WO2002081717A3 (fr) * 2001-04-06 2002-12-12 Asa Spezialenzyme Gmbh Production de pimaricine et de derives de pimaricine et leur utilisation pour la protection phytosanitaire
EP2260706A3 (fr) * 2005-10-04 2011-05-04 DSM IP Assets B.V. Composition anti-fungicide ameliorée
WO2007039572A1 (fr) * 2005-10-04 2007-04-12 Dsm Ip Assets B.V. Préparation antifongique améliorée
US8187844B2 (en) 2005-10-04 2012-05-29 Dsm Ip Assets B.V. Anti-fungal composition
US8536144B2 (en) 2005-10-04 2013-09-17 Dsm Ip Assets B.V. Anti-fungal composition
WO2014085565A1 (fr) * 2012-11-29 2014-06-05 Bayer Cropscience Lp Procédés de contrôle de pathogènes fongiques à l'aide de fongicides polyène
CN104837343A (zh) * 2012-11-29 2015-08-12 拜尔农作物科学有限合伙人公司 使用多烯杀真菌剂防治真菌病原体的方法
WO2014191449A1 (fr) * 2013-05-31 2014-12-04 Dsm Ip Assets B.V. Agriculture microbienne
WO2014191450A1 (fr) * 2013-05-31 2014-12-04 Dsm Ip Assets B.V. Agriculture microbienne

Also Published As

Publication number Publication date
JPH07500243A (ja) 1995-01-12
MX9204345A (es) 1994-05-31
CN1068704A (zh) 1993-02-10
AU2397792A (en) 1993-02-23
JP2714483B2 (ja) 1998-02-16
CA2114102A1 (fr) 1993-02-04
CA2114102C (fr) 2002-09-17

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