WO2011017367A2 - Water and feed preservative - Google Patents

Water and feed preservative Download PDF

Info

Publication number
WO2011017367A2
WO2011017367A2 PCT/US2010/044305 US2010044305W WO2011017367A2 WO 2011017367 A2 WO2011017367 A2 WO 2011017367A2 US 2010044305 W US2010044305 W US 2010044305W WO 2011017367 A2 WO2011017367 A2 WO 2011017367A2
Authority
WO
WIPO (PCT)
Prior art keywords
acid
feed
polysorbate
span
water
Prior art date
Application number
PCT/US2010/044305
Other languages
French (fr)
Other versions
WO2011017367A3 (en
Inventor
Kurt Richardson
Julio Pimentel
James D. Wilson
Original Assignee
Anitox Corporation
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=43544912&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2011017367(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to KR1020127005718A priority Critical patent/KR101871002B1/en
Priority to CN2010800339148A priority patent/CN102469810B/en
Priority to EP10807056.6A priority patent/EP2461700B1/en
Priority to RU2012105054/13A priority patent/RU2516279C2/en
Priority to BR112012001880-9A priority patent/BR112012001880B1/en
Priority to AU2010279511A priority patent/AU2010279511B2/en
Priority to US13/388,449 priority patent/US10785975B2/en
Application filed by Anitox Corporation filed Critical Anitox Corporation
Priority to CA2770124A priority patent/CA2770124C/en
Priority to JP2012523716A priority patent/JP5655075B2/en
Priority to MX2012001525A priority patent/MX2012001525A/en
Priority to ES10807056.6T priority patent/ES2575217T3/en
Priority to UAA201201643A priority patent/UA104899C2/en
Publication of WO2011017367A2 publication Critical patent/WO2011017367A2/en
Publication of WO2011017367A3 publication Critical patent/WO2011017367A3/en
Priority to EG2012010112A priority patent/EG26433A/en
Priority to IL217811A priority patent/IL217811A/en
Priority to ZA2012/01502A priority patent/ZA201201502B/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, 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
    • A01N37/02Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K20/00Accessory food factors for animal feeding-stuffs
    • A23K20/10Organic substances
    • A23K20/105Aliphatic or alicyclic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K20/00Accessory food factors for animal feeding-stuffs
    • A23K20/10Organic substances
    • A23K20/111Aromatic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23KFODDER
    • A23K20/00Accessory food factors for animal feeding-stuffs
    • A23K20/10Organic substances
    • A23K20/116Heterocyclic compounds
    • A23K20/121Heterocyclic compounds containing oxygen or sulfur as hetero atom
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463Organic compounds; Microorganisms; Enzymes
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463Organic compounds; Microorganisms; Enzymes
    • A23L3/3472Compounds of undetermined constitution obtained from animals or plants
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463Organic compounds; Microorganisms; Enzymes
    • A23L3/3481Organic compounds containing oxygen
    • A23L3/3508Organic compounds containing oxygen containing carboxyl groups
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463Organic compounds; Microorganisms; Enzymes
    • A23L3/3535Organic compounds containing sulfur
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/90Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in food processing or handling, e.g. food conservation
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • a method to extend the shelf-life of water, feed and major feed ingredients by spray -treating or admixing a mixture of organic acids containing pelargonic acid.
  • Food borne illnesses are common problems for millions of people around the world. Food borne illnesses are caused by many different microorganisms, including infections by
  • Salmonella is a facultative, intracellular pathogen capable of infesting humans and animals resulting in infection. After ingestion, Salmonella can escape the confines of the intestine, can penetrate the intestine and can be transported by the blood to internal organs (Henderson, S. et. al., 1999, Early events in the pathogenesis of avian salmonellosis, Infec. Immun. 67(7): 3580- 3586).
  • Some factors present in eggs help to maintain lower Salmonella levels in freshly laid eggs (0.6% incidence) even though eggs from the oviduct of the same hen showed higher salmonella levels (29% incidence); these factors may include antibodies, antibacterial enzymes and iron-sequestering and bacterial protease-inhibiting proteins in yolk and albumen (Keller, L. H. et. al., 1995, Salmonella enteritidis colonization of the reproductive tract and forming and freshly laid eggs of chickens. Infec. Immun. 63(7): 2443- 2449)
  • the incidence of Salmonella, K coli and Enterococais varies depending on the type of ingredients used in animal feed manufacturing. There is higher incidence of Salmonella in rendered animal food (35%) than in plant-based food (5%). The incidence of E. coli is similar in both animals and plant derived foods (40%), but the incidence of Enferococcus is 80% in animal and 91% in plant-derived foods. The incidence of Salmonella contamination in animal feed is higher in mash form than in pellet form. Pelletization under high-temperature and high-pressure conditions reduces the number not only of Salmonella but also other bacteria. A problem with simple pelletization is that there is no protection against microbial recontami nation of the feed before it is consumed by the animal, such as in bagging, transport and feeders.
  • scours in calves has economic importance. More than 90% of scours in calves is produced by E. coli and Salmonella and Clostridia. Preventive methods are known, such as (1) vaccination of the mothers in order to passively transfer antibodies in colostrum; (2) use of immune supplements for milk replacers; (3) use of probiotics to create a healthy environment in the gastro-intestinal tract, and (4) changes in husbandry. None of these protective measures are 100% effective.
  • E. coli and Salmonella are the main microorganisms involved in diarrhea in swine.
  • SEW segregated early weaning
  • the basis of early weaning is that the earlier the piglets are weaned from the sow, the lesser the chances of crossover diseases between sow and piglets.
  • the preferred method of treatment is with antibiotics.
  • EU European Community
  • AU the states of the EU have banned the use of antibiotics as growth promoters, and this has been extended to all countries that export meat or its derivatives to the EU.
  • water additives such as quaternary ammonium products, chlorite-based products, chlorination, chlorine dioxide, and organic acids (acetic, sorbate, ascorbic, citric, formic).
  • Methods for preservation of feed include heat treatment, organic acids, formaldehyde, essential oils and irradiation.
  • Salmonella with organic acids requires high levels of treatment, which implies high cost to the animal industry. Irradiation of feed is not cost effective and not consumer friendly.
  • Sodium percabonate is a powerful oxidizer that is used as an antimicrobial in feed at levels of 1-2% of the diet.
  • Chlorate treatment is recommended for E coli and Salmonella since these bacteria have the enzyme nitrate reductase that reduces chlorate to chlorite, which has antimicrobial properties.
  • Salmonella-challenged pigs when administered chlorate ions through water before slaughter had reduced bacteria counts in the intestine contents and lymph tissue (Anderson, R C. et. al 2004, Effect of drinking-water administration of experimental chlorate ion preparations on Salmonella enterica serovar Typhhmirhim colonization in weaned and finished pigs, Vet. Res. Comm. 28(3): 179-189).
  • Organic acids have been a major additive to reduce the incidence of food borne infections.
  • the use of short-, medium- and long-chain fatty acids e.g., formic, propionic, butyric, lactic, citric, malic and others have been reported to be successful in some instances.
  • Short-chain fatty acids exert their antimicrobial activity because undissociated RCOOH (non-ionized) acid groups are lipid-permeable, and, therefore, can cross the microbial cell wall and dissociate in the more alkaline interior of the microorganism (RCOOH— > RCOO ' + H + ) making the cytoplasm unstable for survival.
  • the use of organic acids, especially formic and propionic acid are well documented in the art. But pelargonic acid is referred to only as a herbicide and a fungicide for plant uses, not for preservation of water and animal feed.
  • Pelargonic acid is a naturally occurring fatty acid found in almost all species of animals and plants. Because it contains nine carbon atoms, it is also called nonanoic acid has the chemical formula It is found at low levels in many common foods and is readily broken down in the environment. It is an oily colorless fluid that solidifies at lower temperatures. It has an unpleasant rancid odor and is almost insoluble in water.
  • Pelargonic acid is used as a non-selective herbicide. Scythe (57% pelargonic acid, 3% related fatty acids and 40% inert material) is a broad-spectrum post-emergence or burn-down herbicide produced by Mycogen/Dow Chemicals. The herbicidal mode of action of pelargonic acid is due first to membrane leakage in the dark or light, and second to peroxidation driven by radicals formed in the light by sensitized chlorophyll displaced from the thylakoid membrane (B. Lederer, T. Fujimori., Y. Tsujino, K. Wakabayashi and P Boger; Phyloloxic activity of middle- chain fatty acids II: peroxidation and membrane effects. Pesticide Biochemistry and Physiology 80: 151-156)
  • MTC minimum inhibitory concentration
  • Trichoderma hahianum a biocontrol for cacao plants, produces pelargonic acid as one of many chemicals, and was effective in controlling the germination and growth of cacao pathogens.
  • Trichoderma harzianum produces nonanoic acid, an inhibitor of spore germination and mycelial growth of two cacao pathogens. Physiological and Molecular Plant Pathology 67:304-307, 2005).
  • US Patent 5,366,995 discloses a method to eradicate fungal and bacterial infections in plants and to enhance the activity of fungicides and bactericides in plants by fatty acids and their derivatives with a formulation containing 80% pelargonic acid or its salts for the control of plants fungi.
  • the fatty acids used primarily have 9 to 18 carbon chains.
  • US Patent 5,342,630 discloses a pesticide for plant uses containing an inorganic salt which enhances the efficacy of 8- to 22-carbon chain fatty acids.
  • One of the examples shows a powder product with 2% pelargonic acid, 2% capric acid, 80% talc, 10% sodium carbonate and 5% potassium carbonate.
  • US Patent 5,093,124 discloses a fungicide and arthropodice for plants comprise of mono alpha carboxylic acids and their salts having a reduced phytotoxicity.
  • a fungicide with 9 to 10 carbons chain at least, partially neutralized by active alkali metal such as potassium.
  • the mixture comprises of 40% active ingredient dissolved in water and includes 10% pelargonic, 10% capric acid and 20% coconut fatty acids all of with are neutralized with potassium hydroxide.
  • US Patent 6,596,763 discloses a method to control skin infection comprised of 6- to 18- carbon chain fatty acids or their derivatives.
  • US Patent 6,103,768 and US Patent 6,136,856 disclose the unique utility of fatty acids and derivatives to eradicate existing fungal and bacterial infections in plants. This method is not preventive but showed effectiveness in established infections. Sharpshooter, a commercially available product, with 80% pelargonic acid, 2% emulsifier and 18% surfactant showed effectiveness against Penicilliutn and Boirytis spp.
  • US Patent 6,638,978 discloses an antimicrobial preservative composed of a glycerol fatty acid ester, a binary mixture of fatty acids (6 to 18 carbon chains) and a second fatty acid (6 to 18 carbon chains) wherein the second fatty acid is different from the first fatty acid, for preservation of food.
  • WO 01/97799 discloses the use of medium-chain fatty acids as antimicrobials agents. It shows that an increase in pH from 6.5 to 7.5 increased the MlC of the short-chain fatty acids containing 6 - 8 carbon chains.
  • Pelargonic acid is used as a component in food contact surface sanitizing solutions in food handling establishments.
  • a product from EcoLab contains 6.49% pelargonic acid as active ingredient to be use as a sanitizer for all food contact surfaces (12 CFR 178.1010 b).
  • the FDA has cleared pelargonic acid as a synthetic food flavoring agent (21 CFR 172.515), as an adjuvant, production aid and sanitizer to be used in contact food (12 CFR 178.1010 b) and in washing or to assist in lye peeling of fruits and vegetables (12 CFR 173.315).
  • Pelargonic acid is listed by the USDA under the USDA list of Authorized Substances, 1990, section 5.14, Fruit and Vegetable Washing Compounds. SUMMARY OF THE INVENTION
  • concentration of C9 acid is 2 to 20 wt.%, based on the total organic acid content.
  • An "organic acid” of the invention is a carboxylic acid compound having straight or branched Ci to Cis hydrocarbon chain, e.g., formic acid, acetic acid, propionic acid, butyric acid and pelargonic acid.
  • a "buffered solution” is one which resists changes in pH when small quantities of an acid or an alkali are added.
  • Buffer capacity is a quantitative measure of the resistance of a buffer solution to pH change on addition of hydroxide ions. Buffering systems of the invention include
  • An "antimicrobial terpene” of the invention may be allyl disulfide, citral, pinene, nerol, geraniol, carvacrol, eugenol, carvone, anethole, camphor, menthol, limonene, farnesol, carotene, thymol, borneol, myrcene, terpenene, linalool, or mixtures thereof.
  • Preferred terpenes are allyl disulfide, thymol, citral, eugenol, carvacrol, and carvone, or mixtures thereof.
  • an effective amount of a compound means that amount which is capable of performing the function of the compound or property for which the effective amount is expressed, such as a non-toxic but sufficient amount to provide an antimicrobial effect. Thus an effective amount may be determined by one of ordinary skill in the art using routine
  • Formulations can vary not only in the concentration of major components i.e. organic acids, but also in the type of terpenes, type of surfactant and water concentration used.
  • the invention can be modified by adding or deleting terpenes and surfactants from the formulations.
  • compositions of the present invention comprise organic acids having 1 to 18 carbons, containing an effective amount of a C 2 ICg or a Cy.Cy mixture, resulting in a synergistic preservative effect.
  • an aqueous solution of the short-chain acids is buffered to a pH between 1 and 5, preferably between pH 1 and 3, then the Cg (Pelargonic) acid is added in an amount from 2 to 20 wt.% along with optional terpenes and surfactants and other additives.
  • Antimicrobial terpenes, plant extracts or essential oils containing terpenes can be used in the invention as well as the more purified terpenes.
  • Terpenes are commercially available or can be produced by various methods known in the art, such as solvent extraction or steam
  • the surfactant can be non-ionic, cationic, or anionic.
  • surfactants include polysorbate 20, polysorbate 80, polysorbate 40, polysorbate 60, polyglyceryl ester, polyglyceryl monooleate, decaglyceryl monocaprylate, propylene glycol dicaprilate, triglycerol monostearate, TweenTM 20, SpanTM 20, SpanTM 40, SpanTM 60, SpanTM 80, ethoxylated castor oil surfactants or mixtures thereof.
  • the total composition can comprise 1% to 100% by weight organic acids, preferably 20 - 95%. Of the organic acid component, 2% to 20% by weight is pelargonic acid and the remaining 98% to 80% by weight is acetic acid, propionic acid or a mixture thereof.
  • the composition may contain 0 to 20% by weight terpenes, preferably 0.5 - 10%, and 0 to 20% by weight surfactant, preferably 0.5 - 5%.
  • the total composition may contain 0 to 99 wt.% water.
  • the present invention is effective against any of these classifications of infective agents present in water, feed and major feed ingredients, in particular, bacteria, mycoplasma, viruses and fungi.
  • compositions and methods of the present invention are effective in preventing many, if not all, of these infections in a great variety of subjects, including humans, other mammals and avians.
  • the present invention includes a method to disinfect water, feed and feed ingredients.
  • the method comprises administering the composition by a variety of means. For example, sprayed onto feed, sprayed onto water, mixed in drinking water, applied to surfaces where water and feed are stored for future uses or consumed daily, added drop wise through a standard medicator or water disinfector, for example in starter, grower and finisher animal houses.
  • composition of the present invention can be used safely and effectively as a preservative for water and feed for all commercially grown animals, for human consumption and external use, for companion animals, and other animals where a low microbial concentration is desired in the feed or water supply.
  • Propionic and acetic acids were buffered with ammonium hydroxide to pHs ranging from 1 to 7 Acid contents of the buffered solutions were determined by a weight to weight ratio calculation to obtain the same acid content in the test solutions. Solutions are added to sterile deionized water to provide a 0.025%, 0.05%, 0.075% and 0.1% acid solution. The pHs of the deionized water solutions were recorded and any problems with solubility noted.
  • ND - MIC can not be determined due to a lack of effect at the highest dose rate.
  • Pu ⁇ ose Of the long chain organic acids, pelargonic was observed to be the most effective based on prior studies. This experiment is to determine if there is a synergistic effect when buffered propionic or acetic acid is combined with pelargonic acid.
  • Acetic acid pelargonic acid (20:80: wt/wt)
  • Propionic and acetic acids were buffered with ammonium hydroxide to a pH of 3 and combined with pelargonic in the ratios listed. Acid content of the buffered solutions was determined by weight to weight ratio calculation (weight of acid/total weight of buffered solution) and adjusted to provide an equal acid value for each treatment. The treatments above were added to sterile deionized water to make at a 0.025% and 0.05% total acid solutions. The pHs of the deionized water solutions were recorded and any problems with solubility noted.
  • Propionic, acetic and pelargonic acids by themselves or in combination as listed were added to sterile deionized water to make at a 0.05%, 0.04%, 0.03%, 0.02% and 0.01% total acid solutions.
  • the pHs of the deionized water solutions were recorded and any problems with solubility noted.
  • 100 ul of a nutrient broth culture of Salmonella typhimurium (ATTC 14028) was added to each dilution tube. After addition, tubes were vortexed and allowed to stand. At 24 hours after addition of the inoculum, 100 ul of the solution was plated on Standard Plate agar (triplicate plates). Plates were incubated at 37°C for 24 hours prior to enumeration.
  • Capric acid (5%, 10% or 20%) diluted in acetic acid or propionic acid was tested to determine its effectiveness against salmonella in feed.
  • Myristic acid (5%, 10% and 20%) diluted in propionic acid was tested to determine its effectiveness against salmonella in feed. Myristic acid was not soluble in acetic acid.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nutrition Science (AREA)
  • Animal Husbandry (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Botany (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Fodder In General (AREA)
  • Medicinal Preparation (AREA)

Abstract

Antimicrobial compositions containing buffered propionic or acetic acid mixed with pelargonic acid.

Description

TITLE OF THE INVENTION
WATER AND FEED PRESERVATIVE BACKGROUND OF THE TNVENTION FIELD OF THE INVENTION
A method to extend the shelf-life of water, feed and major feed ingredients by spray -treating or admixing a mixture of organic acids containing pelargonic acid.
BACKGROUND
Food borne illnesses are common problems for millions of people around the world. Food borne illnesses are caused by many different microorganisms, including infections by
Campylobacter spp.. Shigella spp., Listeria monocytogenes, Yersenia enter olilica , Salmonella spp. and E. coli which are prevalent in many countries. CDC statistics in the United States suggest that 76 million people become sick each year due to consumption of undercooked meat, eggs, shellfish, unpasteurized dairy products, and unwashed vegetables. Food producing animals are the major reservoir of non-typhi serotypes of Salmonella enterica, which causes an estimated 1.4 million illnesses, 16,400 hospitalizations and 580 U.S. deaths/year.
Salmonella is a facultative, intracellular pathogen capable of infesting humans and animals resulting in infection. After ingestion, Salmonella can escape the confines of the intestine, can penetrate the intestine and can be transported by the blood to internal organs (Henderson, S. et. al., 1999, Early events in the pathogenesis of avian salmonellosis, Infec. Immun. 67(7): 3580- 3586).
The majority of salmonellosis cases in humans appear due to consumption of hen's eggs. Two days after hens are orally challenged with Salmonella, the bacteria can be detected in the spleen, liver, heart, gall bladder tissues, intestinal tissues and various sections of the oviduct (Humphrey, TJ. et. al, 1994, Contamination of egg shell and contents with Salmonella enteritidis, Int. J. Food Microbiol 21 (1-2): 31-40). Some factors present in eggs help to maintain lower Salmonella levels in freshly laid eggs (0.6% incidence) even though eggs from the oviduct of the same hen showed higher salmonella levels (29% incidence); these factors may include antibodies, antibacterial enzymes and iron-sequestering and bacterial protease-inhibiting proteins in yolk and albumen (Keller, L. H. et. al., 1995, Salmonella enteritidis colonization of the reproductive tract and forming and freshly laid eggs of chickens. Infec. Immun. 63(7): 2443- 2449)
The incidence of Salmonella, K coli and Enterococais varies depending on the type of ingredients used in animal feed manufacturing. There is higher incidence of Salmonella in rendered animal food (35%) than in plant-based food (5%). The incidence of E. coli is similar in both animals and plant derived foods (40%), but the incidence of Enferococcus is 80% in animal and 91% in plant-derived foods. The incidence of Salmonella contamination in animal feed is higher in mash form than in pellet form. Pelletization under high-temperature and high-pressure conditions reduces the number not only of Salmonella but also other bacteria. A problem with simple pelletization is that there is no protection against microbial recontami nation of the feed before it is consumed by the animal, such as in bagging, transport and feeders.
The presence of scours in calves has economic importance. More than 90% of scours in calves is produced by E. coli and Salmonella and Clostridia. Preventive methods are known, such as (1) vaccination of the mothers in order to passively transfer antibodies in colostrum; (2) use of immune supplements for milk replacers; (3) use of probiotics to create a healthy environment in the gastro-intestinal tract, and (4) changes in husbandry. None of these protective measures are 100% effective.
The incidence of diarrhea in neonates and weaned piglets is also very high. Again, E. coli and Salmonella are the main microorganisms involved in diarrhea in swine. One of the preferred methods for preventing this problem is segregated early weaning (SEW). The basis of early weaning is that the earlier the piglets are weaned from the sow, the lesser the chances of crossover diseases between sow and piglets. In both calf and piglet scours, the preferred method of treatment is with antibiotics.
The European Community (EU) has banned the use of five antibiotics and FDA in the United States is banning the use of fluoroquinolone in animals due to the development of resistance to this antibiotic. Bacterial resistance has encouraged the development of antibiotic-alternative products. AU the states of the EU have banned the use of antibiotics as growth promoters, and this has been extended to all countries that export meat or its derivatives to the EU.
Many products have been developed for the preservation of water and feed for animal uses, including water additives such as quaternary ammonium products, chlorite-based products, chlorination, chlorine dioxide, and organic acids (acetic, sorbate, ascorbic, citric, formic). Methods for preservation of feed include heat treatment, organic acids, formaldehyde, essential oils and irradiation. The elimination of Salmonella with organic acids requires high levels of treatment, which implies high cost to the animal industry. Irradiation of feed is not cost effective and not consumer friendly. Sodium percabonate is a powerful oxidizer that is used as an antimicrobial in feed at levels of 1-2% of the diet.
Chlorate treatment is recommended for E coli and Salmonella since these bacteria have the enzyme nitrate reductase that reduces chlorate to chlorite, which has antimicrobial properties. Salmonella-challenged pigs when administered chlorate ions through water before slaughter had reduced bacteria counts in the intestine contents and lymph tissue (Anderson, R C. et. al 2004, Effect of drinking-water administration of experimental chlorate ion preparations on Salmonella enterica serovar Typhhmirhim colonization in weaned and finished pigs, Vet. Res. Comm. 28(3): 179-189).
Organic acids have been a major additive to reduce the incidence of food borne infections. The use of short-, medium- and long-chain fatty acids, e.g., formic, propionic, butyric, lactic, citric, malic and others have been reported to be successful in some instances. Short-chain fatty acids exert their antimicrobial activity because undissociated RCOOH (non-ionized) acid groups are lipid-permeable, and, therefore, can cross the microbial cell wall and dissociate in the more alkaline interior of the microorganism (RCOOH— > RCOO' + H+) making the cytoplasm unstable for survival. The use of organic acids, especially formic and propionic acid, are well documented in the art. But pelargonic acid is referred to only as a herbicide and a fungicide for plant uses, not for preservation of water and animal feed.
Pelargonic acid is a naturally occurring fatty acid found in almost all species of animals and plants. Because it contains nine carbon atoms, it is also called nonanoic acid has the chemical formula
Figure imgf000004_0001
It is found at low levels in many common foods and is readily broken down in the environment. It is an oily colorless fluid that solidifies at lower temperatures. It has an unpleasant rancid odor and is almost insoluble in water.
Pelargonic acid is used as a non-selective herbicide. Scythe (57% pelargonic acid, 3% related fatty acids and 40% inert material) is a broad-spectrum post-emergence or burn-down herbicide produced by Mycogen/Dow Chemicals. The herbicidal mode of action of pelargonic acid is due first to membrane leakage in the dark or light, and second to peroxidation driven by radicals formed in the light by sensitized chlorophyll displaced from the thylakoid membrane (B. Lederer, T. Fujimori., Y. Tsujino, K. Wakabayashi and P Boger; Phyloloxic activity of middle- chain fatty acids II: peroxidation and membrane effects. Pesticide Biochemistry and Physiology 80: 151-156)
Chadeganipour and Haims [Antifungal activities of pelargonic and capric acid on
Microsporum gypseum Mycoses Vol. 44, Number 3-4 pp 109-112, 2001) showed that the minimum inhibitory concentration (MTC) to prevent growth of M gypseum on solid media was 0.02 mg/ml capric acid, and 0.04 mg/ml for pelargonic acid. In liquid media it was 0.075 mg/ml capric acid, and 0.05 mg/ml pelargonic. These acids were tested independently and not as a mixture.
N. Hirazawa, et al. (Antiparasitic effect of medium-chain fatty acids against ciliated
Crptocaryon irritans infestation in the red sea bream Pagrus major, Aquaculture, 198:219-228, 2001) found that nonanoic acid as well as Ce to Cio fatty acids were effective in controlling the growth of the parasite C. irritans and that Cs, Oj and Cio were the more potent.
It was found that Trichoderma hahianum, a biocontrol for cacao plants, produces pelargonic acid as one of many chemicals, and was effective in controlling the germination and growth of cacao pathogens. (M. Aneja, T. Gianfagna and P. Hebbar,. Trichoderma harzianum produces nonanoic acid, an inhibitor of spore germination and mycelial growth of two cacao pathogens. Physiological and Molecular Plant Pathology 67:304-307, 2005).
Published patent application US2004/0266852, discloses a fungicide for agricultural uses composed of one or more fatty acids and one or more organic acids different from the fatty acid. In the mixture of the organic acids with the fatty acid, the organic acid acts as a potent synergist for the fatty acid as a fungicide.
US Patent 5,366,995, discloses a method to eradicate fungal and bacterial infections in plants and to enhance the activity of fungicides and bactericides in plants by fatty acids and their derivatives with a formulation containing 80% pelargonic acid or its salts for the control of plants fungi. The fatty acids used primarily have 9 to 18 carbon chains.
US Patent 5,342,630 discloses a pesticide for plant uses containing an inorganic salt which enhances the efficacy of 8- to 22-carbon chain fatty acids. One of the examples shows a powder product with 2% pelargonic acid, 2% capric acid, 80% talc, 10% sodium carbonate and 5% potassium carbonate. US Patent 5,093,124 discloses a fungicide and arthropodice for plants comprise of mono alpha carboxylic acids and their salts having a reduced phytotoxicity. Preferably a fungicide with 9 to 10 carbons chain at least, partially neutralized by active alkali metal such as potassium. The mixture comprises of 40% active ingredient dissolved in water and includes 10% pelargonic, 10% capric acid and 20% coconut fatty acids all of with are neutralized with potassium hydroxide.
US Patent 6,596,763 discloses a method to control skin infection comprised of 6- to 18- carbon chain fatty acids or their derivatives.
US Patent 6,103,768 and US Patent 6,136,856 disclose the unique utility of fatty acids and derivatives to eradicate existing fungal and bacterial infections in plants. This method is not preventive but showed effectiveness in established infections. Sharpshooter, a commercially available product, with 80% pelargonic acid, 2% emulsifier and 18% surfactant showed effectiveness against Penicilliutn and Boirytis spp.
US Patent 6,638,978 discloses an antimicrobial preservative composed of a glycerol fatty acid ester, a binary mixture of fatty acids (6 to 18 carbon chains) and a second fatty acid (6 to 18 carbon chains) wherein the second fatty acid is different from the first fatty acid, for preservation of food.
WO 01/97799 discloses the use of medium-chain fatty acids as antimicrobials agents. It shows that an increase in pH from 6.5 to 7.5 increased the MlC of the short-chain fatty acids containing 6 - 8 carbon chains.
Pelargonic acid is used as a component in food contact surface sanitizing solutions in food handling establishments. A product from EcoLab contains 6.49% pelargonic acid as active ingredient to be use as a sanitizer for all food contact surfaces (12 CFR 178.1010 b).
The FDA has cleared pelargonic acid as a synthetic food flavoring agent (21 CFR 172.515), as an adjuvant, production aid and sanitizer to be used in contact food (12 CFR 178.1010 b) and in washing or to assist in lye peeling of fruits and vegetables (12 CFR 173.315).
Pelargonic acid is listed by the USDA under the USDA list of Authorized Substances, 1990, section 5.14, Fruit and Vegetable Washing Compounds. SUMMARY OF THE INVENTION
An object of the invention is to provide an antibacterial composition for extending the shelf-life of water, feed or feed ingredients, comprising: 1% to 99 wt. % of organic acids in aqueous solution, which is a C2.C9 or C3:C9 mixture of organic acids buffered to a pH = 1 - 5; 0 to 20% by weight terpenes, and 0.5 - 10% surfactants; wherein the concentration of C9 acid is 2 to 20 wt.%, based on the total organic acid content.
Another object of the invention is to provide a method for extending the shelf-life of water, feed or feed ingredients, comprising: spray-treating or admixing to water, feed or major feed ingredients, an effective amount of a composition comprising 1% to 99 wt. % of organic acids in aqueous solution, which is a C2.C9 or Cy.Cg mixture of organic acids buffered to a pH = 1 - 5; 0 to 20% by weight terpenes, and 0.5 - 10% surfactants;
wherein the concentration of C9 acid is 2 to 20 wt.%, based on the total organic acid content.
DETAILED DESCRIPTION OF THE INVENTION
Definitions:
An "organic acid" of the invention is a carboxylic acid compound having straight or branched Ci to Cis hydrocarbon chain, e.g., formic acid, acetic acid, propionic acid, butyric acid and pelargonic acid.
A "buffered solution" is one which resists changes in pH when small quantities of an acid or an alkali are added. Buffer capacity is a quantitative measure of the resistance of a buffer solution to pH change on addition of hydroxide ions. Buffering systems of the invention include
HCl, Sodium citrate pH = 1 - 5
Citric acid, Sodium citrate pH = 2.5 - 5.6
Acetic acid, Sodium acetate pH = 3.7 - 5.6
NH4Cl, NH4OH pH 1 to 11
An "antimicrobial terpene" of the invention may be allyl disulfide, citral, pinene, nerol, geraniol, carvacrol, eugenol, carvone, anethole, camphor, menthol, limonene, farnesol, carotene, thymol, borneol, myrcene, terpenene, linalool, or mixtures thereof. Preferred terpenes are allyl disulfide, thymol, citral, eugenol, carvacrol, and carvone, or mixtures thereof. The term "effective amount" of a compound means that amount which is capable of performing the function of the compound or property for which the effective amount is expressed, such as a non-toxic but sufficient amount to provide an antimicrobial effect. Thus an effective amount may be determined by one of ordinary skill in the art using routine
experimentation.
Formulations can vary not only in the concentration of major components i.e. organic acids, but also in the type of terpenes, type of surfactant and water concentration used. The invention can be modified by adding or deleting terpenes and surfactants from the formulations.
The term "synergistic effect" or "synergy" means an improved preservative effect when the ingredients are used as a mixture compared to the expected additive effect based on each component used alone.
Compositions of the present invention comprise organic acids having 1 to 18 carbons, containing an effective amount of a C2ICg or a Cy.Cy mixture, resulting in a synergistic preservative effect. In general, an aqueous solution of the short-chain acids is buffered to a pH between 1 and 5, preferably between pH 1 and 3, then the Cg (Pelargonic) acid is added in an amount from 2 to 20 wt.% along with optional terpenes and surfactants and other additives.
Antimicrobial terpenes, plant extracts or essential oils containing terpenes can be used in the invention as well as the more purified terpenes. Terpenes are commercially available or can be produced by various methods known in the art, such as solvent extraction or steam
extraction/distillation or chemically synthesized.
The surfactant can be non-ionic, cationic, or anionic. Examples of surfactants include polysorbate 20, polysorbate 80, polysorbate 40, polysorbate 60, polyglyceryl ester, polyglyceryl monooleate, decaglyceryl monocaprylate, propylene glycol dicaprilate, triglycerol monostearate, Tween™ 20, Span™ 20, Span™ 40, Span™ 60, Span™ 80, ethoxylated castor oil surfactants or mixtures thereof.
The total composition can comprise 1% to 100% by weight organic acids, preferably 20 - 95%. Of the organic acid component, 2% to 20% by weight is pelargonic acid and the remaining 98% to 80% by weight is acetic acid, propionic acid or a mixture thereof. The composition may contain 0 to 20% by weight terpenes, preferably 0.5 - 10%, and 0 to 20% by weight surfactant, preferably 0.5 - 5%. The total composition may contain 0 to 99 wt.% water. The present invention is effective against any of these classifications of infective agents present in water, feed and major feed ingredients, in particular, bacteria, mycoplasma, viruses and fungi. Examples of these infective agents are Staphylococcus aureus, Aspergillus fiimigatus. Mycoplasma iowae, Sclerotinta homeocarpa, Rhizoctonia solani, Colletolrichum graminicola, Peiiicillum sp., Mycoplasma pneumoniae, IL coli, Salmonella sp., Clostridia sp., Campylobacter sp. and others. The compositions and methods of the present invention are effective in preventing many, if not all, of these infections in a great variety of subjects, including humans, other mammals and avians.
The present invention includes a method to disinfect water, feed and feed ingredients. The method comprises administering the composition by a variety of means. For example, sprayed onto feed, sprayed onto water, mixed in drinking water, applied to surfaces where water and feed are stored for future uses or consumed daily, added drop wise through a standard medicator or water disinfector, for example in starter, grower and finisher animal houses.
The composition of the present invention can be used safely and effectively as a preservative for water and feed for all commercially grown animals, for human consumption and external use, for companion animals, and other animals where a low microbial concentration is desired in the feed or water supply.
Throughout this application, various publications are referenced. The disclosures of these publications are hereby incorporated by reference in their entireties into this application.
EXAMPLE 1 - Evaluation of Buffered Organic acids
Purpose: To determine the effect of pH on the antimicrobial activity of acetic and propionic acid
Treatments:
1) Control (negative control)
2) Formic acid : Propionic acid (90: 10 ratio, positive control)
3) Acetic acid (pH 1)
4) Acetic acid (pH 2)
5) Acetic acid (pH 3)
6) Acetic acid (pH 4)
7) Acetic acid (pH 5)
8) Acetic acid (pH 6)
9) Acetic acid (pH 7)
10) Propionic acid (pH 1)
1 1 ) Propionic acid (pH 2)
12) Propionic acid (pH 3)
13) Propionic acid (pH 4)
14) Propionic acid (pH 5)
15) Propionic acid (pH 6)
16) Propionic acid (pH 7)
Procedure:
Propionic and acetic acids were buffered with ammonium hydroxide to pHs ranging from 1 to 7 Acid contents of the buffered solutions were determined by a weight to weight ratio calculation to obtain the same acid content in the test solutions. Solutions are added to sterile deionized water to provide a 0.025%, 0.05%, 0.075% and 0.1% acid solution. The pHs of the deionized water solutions were recorded and any problems with solubility noted.
100 ul of a nutrient broth culture of Salmonella tvphimurium (ATTC 14028) was added to each dilution tube. After addition, tubes were vortexed and allowed to stand. At 4 and 24 hours after addition of the inoculum, 100 ul of the solution was plated on Standard Plate agar (triplicate plates). Plates were incubated at 37°C for 24 hours prior to enumeration. The minimum effective dose of each acid was determined by linear regression.
Results:
Figure imgf000011_0001
Figure imgf000012_0001
Figure imgf000013_0001
ND - MIC can not be determined due to a lack of effect at the highest dose rate.
Conclusions: Buffering of acetic or propionic acid with ammonia decreased the effectiveness of the product to Salmonella. The break point appears to be between a pH of 3-4.
EXAMPLE 2 - Evaluation of Individual Organic Acids
Purpose: To determine the effect of carbon chain length of organic acids on antimicrobial activity
Treatments:
1) Control
2) Formic acid : Propionic acid (90: 10 ratio; positive control)
3) Formic acid
4) Acetic acid
5) Propionic acid
6) Butyric acid
7) Valeric acid
8) Caproic acid
9) Oenanthic acid
10)Caprylic acid
l l) Pelargonic acid
12) Laurie acid
13) Potassium hydroxide Procedure:
In this experiment, the effect of free fatty acids was evaluated. Several long chain fatty acids (caprylic, pelargonic and lauric) were not soluble in water and KOH was used to get these acids into solution in water (final solution contained equal amounts by weights of acid and-KOH. Acid content of the solutions was determined by a weight to weight ratio calculation (weight of acid/total weight of buffered solution). Solutions are added to sterile deionized water to provide a 0.025%, 0.05%, 0.075% and 0.1% acid solutions. The pH of the deionized water solutions was recorded and any problems with solubility noted
100 ul of a nutrient broth culture of Salmonella tvphimurium (ATTC 14028) was added to each dilution tube. After addition, tubes were vortexed and allowed to stand. At 4 and 24 hours after addition of the inoculum, 100 ul of the solution was plated on agar (triplicate plates). Plates were incubated at 37°C for 24 hours prior to enumeration. The minimum effective dose of each acid was be determined by linear regression:
Figure imgf000015_0001
Figure imgf000016_0001
Figure imgf000017_0001
Conclusions: No direct relationship was observed to occur between the efficacy against Salmonella and organic acid chain length. This contrasts the effects reported for acid chain length and anti-fungal efficacy. The activity of caprylic, pelargonic and lauric can not be compared to the shorter chain acids due to the use of KOH.
EXAMPLE 3 - Buffered Organic Acids Mixtures
Puφose: Of the long chain organic acids, pelargonic was observed to be the most effective based on prior studies. This experiment is to determine if there is a synergistic effect when buffered propionic or acetic acid is combined with pelargonic acid.
Test Products:
1) Control
2) Formic acid . Propionic acid (90. 10 ratio, positive control)
3) Acetic acid
4) Acetic acid: pelargonic acid (80:20: wtΛvt)
5) Acetic acid: pelargonic acid (60:40: wt/wt)
6) Acetic acid: pelargonic acid (40:60: wt/wt)
7) Acetic acid: pelargonic acid (20:80: wt/wt)
8) Propionic acid
9) Propionic acid: pelargonic acid (80:20: wt/wt)
10) Propionic acid: pelargonic acid (60:40: wt/wt)
11) Propionic acid: pelargonic acid (40:60: wt/wt)
12) Propionic acid: pelargonic acid (20:80: wt/wt)
13) Pelargonic acid
Procedure: Propionic and acetic acids were buffered with ammonium hydroxide to a pH of 3 and combined with pelargonic in the ratios above. Acid content of the buffered solutions was determined by weight to weight ratio calculation (weight of acid/total weight of buffered solution) and adjusted to provide an equal acid value for each treatment. The treatments above were added to sterile deionized water to make at a 0.025%, 0.05%, 0.075% and 0.1% total acid solutions. The pHs of the deionized water solutions were recorded and any problems with solubility noted.
100 ul of a nutrient broth culture of Salmonella typhimurium (ATTC 14028) was added to each dilution tube. After addition, tubes were vortexed and allowed to stand. At 4 and 24 hours after addition of the inoculum, 100 ul of the solution was plated on Standard Plate agar (triplicate plates). Plates were incubated at 370C for 24 hours prior to enumeration. The minimum effective dose of each acid was determined by linear regression.
Figure imgf000019_0001
Figure imgf000020_0001
Figure imgf000020_0002
Conclusion: The addition of pelargonic acid to propionic or acetic acid resulted in an increase in efficacy.
STUDY 4
Propionic and acetic acids were buffered with ammonium hydroxide to a pH of 3 and combined with pelargonic in the ratios listed. Acid content of the buffered solutions was determined by weight to weight ratio calculation (weight of acid/total weight of buffered solution) and adjusted to provide an equal acid value for each treatment. The treatments above were added to sterile deionized water to make at a 0.025% and 0.05% total acid solutions. The pHs of the deionized water solutions were recorded and any problems with solubility noted.
100 ul of a nutrient broth culture of Salmonella tvphimurium (ATTC 14028) was added to each dilution tube. After addition, tubes were vortexed and allowed to stand. At 4 and 24 hours after addition of the inoculum, 100 ul of the solution was plated on Standard Plate agar (triplicate plates). Plates were incubated at 37°C for 24 hours prior to enumeration.
Figure imgf000022_0001
Conclusion: The addition of pelargonic acid (1 - 20%) to propionic or acetic acid resulted in an increase in efficacy against salmonella. STUDY 5
Propionic, acetic and pelargonic acids by themselves or in combination as listed were added to sterile deionized water to make at a 0.05%, 0.04%, 0.03%, 0.02% and 0.01% total acid solutions. The pHs of the deionized water solutions were recorded and any problems with solubility noted. 100 ul of a nutrient broth culture of Salmonella typhimurium (ATTC 14028) was added to each dilution tube. After addition, tubes were vortexed and allowed to stand. At 24 hours after addition of the inoculum, 100 ul of the solution was plated on Standard Plate agar (triplicate plates). Plates were incubated at 37°C for 24 hours prior to enumeration.
Figure imgf000023_0001
UD= Unable to determine
Conclusion: Test showed increased efficacy by mixing Propionic/Pelargonic (95/5) and
Acetic/Pelargonic (95/5) 24 hours after treatment.
STUDY 6
Capric acid (5%, 10% or 20%) diluted in acetic acid or propionic acid was tested to determine its effectiveness against salmonella in feed.
Commercial poultry feed amended with Salmonella typhimurium (ATTC 14028) was treated with 1 or 3 kg/MT of the solutions listed below. Twenty four hours after treatment, 10 gr of feed was added to 90 ml Butterfield buffer, mixed and then 100 ul of the solution was plated on
Standard Plate agar (triplicate plates). Plates were incubated at 370C for 24 hours prior to enumeration.
Figure imgf000024_0001
Addition of capric acid to acetic or propionic acid at concentrations of 5-20% did not appear to significantly improve the efficacy of the organic acid against Salmonella in feed. STUDY 7
Myristic acid (5%, 10% and 20%) diluted in propionic acid was tested to determine its effectiveness against salmonella in feed. Myristic acid was not soluble in acetic acid.
Commercial poultry feed amended with Salmonella typhimurium (ATTC 14028) was treated with 1 or 3 kg/MT of the solutions listed below. Twenty four hours after treatment, 10 gr of feed was added to 90 ml Butterfield buffer, mixed and then 100 ul of the solution was plated on Standard Plate agar (triplicate plates). Plates were incubated at 370C for 24 hours prior to enumeration.
Figure imgf000025_0001
No beneficial effect in efficacy was observed when myristic acid was added at 5-20% to propionic acid compared to the standard propionic acid combination.
STUDY 8
Laurie acid (5%, 10%, 20%) diluted with propionic acid was tested to determine its effectiveness against salmonella in feed.
Commercial poultry feed amended with Salmonella typhimurium (ATTC 14028) was treated with 1 or 2 kg/MT of the solutions listed below. Twenty four hours after treatment, 10 gr of feed was added to 90 ml Butterfield buffer, mixed and then 100 ul of the solution was plated on Standard Plate agar (triplicate plates). Plates were incubated at 37°C for 24 hours prior to enumeration.
Figure imgf000026_0001
No beneficial effect was observed when lauric acid (5-20%) was added to propionic acid compared to the standard propionic acid combination.
It will be apparent to those skilled in the art that a number of modifications and variations may be made in the present invention without departing from the scope of the invention. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the invention being indicated by the following claims.

Claims

1. An antimicrobial composition for extending the shelf-life of water, feed or feed
ingredients, comprising:
1% to 99 wt. % of organic acids in aqueous solution, which is a C2:C9 or C3:C9 mixture of organic acids, buffered to pH = 1 - 5;
0 to 20% by weight terpenes, and
0.5 - 10% surfactants;
wherein the C9 acid concentration is 2 to 20 wt.%, based on the total organic acid content.
2. The antimicrobial composition of claim 1, which is buffered to pH = 1 - 3.
3. The antimicrobial composition of claim 1, wherein the surfactant is polysorbate 20, polysorbate 80, polysorbate 40, polysorbate 60, polyglyceryl ester, polyglyceryl monooleate, decaglyceryl monocaprylate, propylene glycol dicaprilate, triglycerol monostearate, Tween™ 20, Span™ 20, Span™ 40, Span™ 60, Span™ 80, ethoxylated castor oil surfactants or mixtures thereof.
4. The antimicrobial composition of claim 1 , wherein the surfactant concentration is 0.5 to 5 wt.%.
5. The antimicrobial composition of claim 1, wherein the terpene is selected from the group consisting of allyl disulfide, citral, pinene, nerol, geraniol, carvacrol, eugenol, carvone, anethole, camphor, menthol, limonene, farnesol, carotene, thymol, bomeol, myrcene, terpenene, linalool, or mixtures thereof.
6. The antimicrobial composition of claim 1, wherein the terpene is selected from the group consisting of allyl disulfide, thymol, citral, eugenol, carvacrol, and carvone, or mixtures thereof.
7. The antimicrobial composition of claim 1, wherein the terpene content is 0.5 - 10 wt.%.
8. A method for extending the shelf-life of water, feed or feed ingredients, comprising: spray-treating or admixing to water, feed or feed ingredients, an effective amount of a composition comprising 1% to 99 wt.% of organic acids in aqueous solution, which is a C2:C9 or C3:C9 mixture of organic acids buffered to a pH = 1 - 5;
0 to 20% by weight terpenes, and
0.5 - 10% surfactants; wherein the concentration of C9 acid is 2 to 20 wt.%, based on the total organic acid content.
9. The method of claim 8, wherein the composition is buffered to pH = 1 - 3.
10. The method of claim 8, wherein the surfactant is polysorbate 20, polysorbate 80,
polysorbate 40, polysorbate 60, polyglyceryl ester, polyglyceryl monooleate, decaglyceryl monocaprylate, propylene glycol dicaprilate, triglycerol monostearate, Tween™ 20, Span™ 20, Span™ 40, Span™ 60, Span™ 80, ethoxylated castor oil surfactants or mixtures thereof.
11. The method of claim 8, wherein the surfactant concentration is 0.5 to 5 wt.%.
12. The method of claim 8, wherein the terpene is selected from the group consisting of allyl disulfide, citral, pinene, nerol, geraniol, carvacrol, eugenol, carvone, anethole, camphor, menthol, limonene, farnesol, carotene, thymol, bomeol, myrcene, terpenene, linalool, or mixtures thereof.
13. The method of claim 8, wherein the terpene is selected from the group consisting of allyl disulfide, thymol, citral, eugenol, carvacrol, and carvone, or mixtures thereof.
14. The method of claim 8, wherein the terpene content is 0.5 - 10 wt.%.
15. The method of claim 8, wherein the composition is effective against bacteria, viruses, mycoplasmas or fungi present in drinking water, feed and feed ingredients.
PCT/US2010/044305 2009-08-06 2010-08-03 Water and feed preservative WO2011017367A2 (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
CA2770124A CA2770124C (en) 2009-08-06 2010-08-03 Water and feed preservative
JP2012523716A JP5655075B2 (en) 2009-08-06 2010-08-03 Preservatives for water and feed
CN2010800339148A CN102469810B (en) 2009-08-06 2010-08-03 Water and feed preservative
MX2012001525A MX2012001525A (en) 2009-08-06 2010-08-03 Water and feed preservative.
BR112012001880-9A BR112012001880B1 (en) 2009-08-06 2010-08-03 antimicrobial composition containing pelargonic acid to extend the shelf life of water, feed and animal feed ingredients and method for employing said composition
AU2010279511A AU2010279511B2 (en) 2009-08-06 2010-08-03 Water and feed preservative
US13/388,449 US10785975B2 (en) 2009-08-06 2010-08-03 Water and feed antimicrobial preservative
KR1020127005718A KR101871002B1 (en) 2009-08-06 2010-08-03 Water and feed preservative
UAA201201643A UA104899C2 (en) 2009-08-06 2010-08-03 Preserving agent for water and feed
EP10807056.6A EP2461700B1 (en) 2009-08-06 2010-08-03 Water and feed preservative
RU2012105054/13A RU2516279C2 (en) 2009-08-06 2010-08-03 Water and food preservative
ES10807056.6T ES2575217T3 (en) 2009-08-06 2010-08-03 Water and feed preservatives
EG2012010112A EG26433A (en) 2009-08-06 2012-01-19 Water and feed preservative
IL217811A IL217811A (en) 2009-08-06 2012-01-29 Water and feed preservative
ZA2012/01502A ZA201201502B (en) 2009-08-06 2012-02-29 Water and feed preservative

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US23193009P 2009-08-06 2009-08-06
US61/231,930 2009-08-06

Publications (2)

Publication Number Publication Date
WO2011017367A2 true WO2011017367A2 (en) 2011-02-10
WO2011017367A3 WO2011017367A3 (en) 2011-06-16

Family

ID=43544912

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/044305 WO2011017367A2 (en) 2009-08-06 2010-08-03 Water and feed preservative

Country Status (23)

Country Link
US (1) US10785975B2 (en)
EP (2) EP2461700B1 (en)
JP (1) JP5655075B2 (en)
KR (1) KR101871002B1 (en)
CN (1) CN102469810B (en)
AU (1) AU2010279511B2 (en)
BR (1) BR112012001880B1 (en)
CA (1) CA2770124C (en)
CL (1) CL2012000181A1 (en)
EG (1) EG26433A (en)
ES (2) ES2575217T3 (en)
HU (2) HUE028283T2 (en)
IL (1) IL217811A (en)
LT (1) LT3023009T (en)
MX (1) MX2012001525A (en)
MY (1) MY174699A (en)
PL (2) PL2461700T3 (en)
PT (2) PT2461700E (en)
RU (1) RU2516279C2 (en)
TR (1) TR201201274T1 (en)
UA (1) UA104899C2 (en)
WO (1) WO2011017367A2 (en)
ZA (1) ZA201201502B (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013059012A1 (en) 2011-10-20 2013-04-25 Anitox Corporation Antimicrobial formulations with pelargonic acid
WO2013081777A1 (en) * 2011-11-30 2013-06-06 Anitox Corporation Antimicrobial mixture of aldehydes, organic acids and organic acid esters
WO2015036433A1 (en) 2013-09-13 2015-03-19 Sopura S.A. Antimicrobial composition
BE1021925B1 (en) * 2013-09-20 2016-01-27 Sopura S.A. ANTIMICROBIAL COMPOSITION.
WO2017138003A1 (en) * 2016-02-11 2017-08-17 Sharon Laboratories Ltd. Antimicrobial preservative compositions
US10785975B2 (en) 2009-08-06 2020-09-29 Anitox Corporation Water and feed antimicrobial preservative
WO2021001578A1 (en) * 2019-07-04 2021-01-07 Nutreco Ip Assets B.V. Feed additive
WO2021069572A1 (en) 2019-10-08 2021-04-15 Taminco Bvba Antimicrobial composition for animal feed
WO2021165436A1 (en) 2020-02-20 2021-08-26 Dsm Ip Assets B.V. Prevention of viral transmission through feed
WO2021214215A1 (en) * 2020-04-23 2021-10-28 Arch Uk Biocides Ltd Synergistic biocide composition with a polyglycerol ester
WO2024116186A1 (en) * 2022-11-30 2024-06-06 Adama Makhteshim Ltd. Stable allyl sulfide compositions

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103229830A (en) * 2013-04-03 2013-08-07 广东工业大学 Gas-phase sustained-release mildew-resistant antistaling agent, and preparation method and application thereof
CN103351031A (en) * 2013-05-10 2013-10-16 湖北中烟工业有限责任公司 Purification agent for prolonging use period of reconstituted tobacco production circulation water, and use method thereof
EP3220744A4 (en) 2014-11-19 2018-08-01 Kansas State University Research Foundation Chemical mitigants in animal feed and feed ingredients
SE539766C2 (en) * 2016-05-20 2017-11-21 Perstorp Ab Animal feed additive effective as broad-spectrum preservative
CN106036034A (en) * 2016-05-20 2016-10-26 四川爱客信生物科技有限公司 Mixed liquid additive for feed and preparation method of mixed liquid additive
WO2019055695A1 (en) * 2017-09-13 2019-03-21 Rrip, Llc Compositions and methods for antimicrobial and immune boosting activity
JP2020535197A (en) * 2017-09-29 2020-12-03 0903608 ビー シー リミテッド Method of delivering synergistic extermination composition and active ingredient
KR102156962B1 (en) * 2017-11-03 2020-09-16 신영근 Composition for domestic animal drinking water and Animal drinking water comprising the same
CN113286513A (en) 2018-09-27 2021-08-20 0903608Bc有限公司 Synergistic pesticide compositions and methods for delivering insecticidal active ingredients
KR20200142173A (en) 2019-06-12 2020-12-22 삼성전자주식회사 A semiconductor device and method of operation of the semiconductor device
WO2021155143A1 (en) * 2020-01-31 2021-08-05 Jeneil Biosurfactant Company, Llc Antimicrobial compositions for modulation of fruit and vegetable tissue necrosis

Family Cites Families (105)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE161131C (en)
CA553057A (en) * 1958-02-11 J. Ferlin Henry Production of bactericidal compositions
US2154449A (en) * 1938-06-15 1939-04-18 Ward Baking Co Process for inhibition of mold
US3615653A (en) 1969-09-24 1971-10-26 Elmer H Fults Treating grains and the like with acidic solution of lignosulfonate
US3682653A (en) 1970-03-02 1972-08-08 Loveland Ind Inc Grain conditioner-modifier chemical combination
IE44924B1 (en) * 1976-05-19 1982-05-19 Bp Chem Int Ltd Preservation process
DE2644351C3 (en) * 1976-10-01 1979-05-17 Basf Ag, 6700 Ludwigshafen Preservatives for animal feed
SU701631A1 (en) * 1978-05-03 1979-12-05 Казахский Филиал Всесоюзного Научно- Исследовательского Института Комбикормовой Промышленности Method of the preservation of feed
US4404040A (en) * 1981-07-01 1983-09-13 Economics Laboratory, Inc. Short chain fatty acid sanitizing composition and methods
US5139779A (en) 1984-09-26 1992-08-18 Sartec Corporation Feed grain conditioning composition and method of tempering feed grain
US5279838A (en) 1984-09-26 1994-01-18 Sartec Corporation Method for processing feed grains
US5240727A (en) 1984-09-26 1993-08-31 Sartec Corporation Feed grain conditioning composition and method of tempering feed grain
US4772481A (en) 1985-03-05 1988-09-20 Frontier Feeds, Inc. Ruminant feed preservative compositions
US4701331A (en) 1985-04-12 1987-10-20 Dox-Al Italia Spa Non-dusty blends of meals or flours with active principles for use in fodder production
GB8514243D0 (en) 1985-06-05 1985-07-10 Diversey Corp Water-dilutable disinfectant composition
GB8525061D0 (en) 1985-10-10 1985-11-13 Bp Chem Int Ltd Antimicrobial additives
CA1331559C (en) 1986-04-21 1994-08-23 Jon Joseph Kabara Antimicrobial preservative compositions and methods
IT1229930B (en) 1988-10-14 1991-09-16 Dox Al Italia Spa PROCEDURE FOR THE PREPARATION OF MIXTURES FOR FOOD AND FOOD USE INCLUDING ACTIVE SUBSTANCES UNIFORMLY DISTRIBUTED
US5198253A (en) 1989-09-28 1993-03-30 Cargill, Incorporated Composition and method for conditioning grains
US5093124A (en) 1989-11-20 1992-03-03 Safer, Inc. Fatty acid-based pesticide with reduced phytotoxicity
US5366995A (en) 1991-05-01 1994-11-22 Mycogen Corporation Fatty acid based compositions for the control of established plant infections
US6103768A (en) 1991-05-01 2000-08-15 Mycogen Corporation Fatty acid based compositions and methods for the control of plant infections and pests
US5260260A (en) 1992-05-11 1993-11-09 Cenex/Land O'lakes Agronomy Company Nonionic herbicidal and surfactant blend
US5342630A (en) 1992-07-01 1994-08-30 Church & Dwight Co., Inc. Environmentally safe pesticide compositions
WO1994006297A1 (en) * 1992-09-22 1994-03-31 Arda Technologies, Co. Antimicrobial composition and method of preparation
NZ256543A (en) * 1992-11-09 1997-10-24 West Agro Inc Sanitizer/biocidal dilutable concentrate comprising germicidal fatty acids
US5591467A (en) 1992-12-30 1997-01-07 Anitox Corporation Contamination-resistant animal feedstuffs
US5505976A (en) 1992-12-30 1996-04-09 Anitox Corporation Contamination-resistant animal feedstuffs
US20020009527A1 (en) 1992-12-30 2002-01-24 Bobby J Bland Contamination-resistant animal feedstuffs
US5547987A (en) 1993-07-19 1996-08-20 Anitox Corporation Pathogen inhibitor for animal feeds
SE502700C2 (en) 1994-04-14 1995-12-11 Berol Nobel Ab Methods of Preparing an Animal Feed Containing Castor Oil Ethoxylate, the Animal Feed Prepared and Its Use
US5587358A (en) 1994-05-09 1996-12-24 Asahi Kasei Kogyo Kabushiki Kaisha Potentiators of antimicrobial activity
CA2144021A1 (en) * 1994-05-10 1995-11-11 V. Gerold Luss Non-toxic, non-corrosive microbicidal composition
US6221381B1 (en) 1994-06-28 2001-04-24 The University Of British Columbia Enhancing milk production by adding to feed a nonionic surfactant coated on a carrier
SE9403484L (en) 1994-10-13 1996-04-14 Akzo Nobel Animal feed with improved nutritional value, process for its preparation and use of a polyethylene glycol compound
US5663152A (en) 1995-01-19 1997-09-02 Asahi Kasei Kogyo Kabushiki Kaisha Potentiators for aminoglycosides
FI100376B (en) 1995-02-06 1997-11-28 Kemira Oyj New preservative composition
DE19612340A1 (en) 1995-03-31 1996-11-07 Schuer Joerg Peter Prof Improving the stability and/or shelf life of perishable prods.
SE506040C2 (en) 1996-02-06 1997-11-03 Akzo Nobel Nv Stable, easy-flowing feed dispersion of molasses and fats and / or oils
US5698599A (en) 1996-03-04 1997-12-16 Rj Reynolds Tobacco Company Method of inhibiting mycotoxin production
WO1997042836A1 (en) 1996-05-10 1997-11-20 Aquatic Feeds Aps Dry fish feed and method of preparing same
FI103704B1 (en) 1996-07-19 1999-08-31 Kemira Chemicals Oy Antimicrobial composition, process for its preparation and its use
DE69739583D1 (en) 1996-11-14 2009-10-29 Lipomedica Ehf TOPICAL COMPOSITIONS CONTAIN AS A THERAPEUTICALLY ACTIVE AGENT A MONOGLYCERIDE FOR THE TREATMENT OF SLEW-TONE INFECTIONS
CZ329799A3 (en) * 1997-03-21 1999-12-15 Basf Aktiengesellschaft Solution and use thereof
US6436444B1 (en) * 1997-09-26 2002-08-20 Ecolab Inc. Acidic aqueous chlorite teat dip providing shelf life sanitizing capacity and tissue protection
US5911915A (en) 1997-12-12 1999-06-15 Colgate Palmolive Company Antimicrobial multi purpose microemulsion
CO5040174A1 (en) 1997-12-12 2001-05-29 Colgate Palmolive Co ANTIMICROBIAL COMPOSITIONS FOR MULTIPLE MICROEMULSION PURPOSES CONTAINING A CATIONIC TENSIOACTIVE
AUPP146598A0 (en) 1998-01-21 1998-02-12 Health And Hygiene International Pty Ltd Fruit and vegetable wash
WO1999041989A1 (en) 1998-02-23 1999-08-26 Monfort, Inc. Method and system for dehairing animals
SE512089C2 (en) 1998-05-26 2000-01-24 Akzo Nobel Surface Chem Ways to prepare a malted dry feed with predetermined water content
US6139890A (en) * 1998-07-21 2000-10-31 Bio-Tek Industries, Inc. Method of extending the shelf life and/or reducing level of bacterial contamination on fruits and vegetables
US6326032B1 (en) * 1998-11-18 2001-12-04 Ecolab Inc. Beverage manufacture and cold aseptic bottling using peroxyacid antimicrobial composition
US6201026B1 (en) 1999-03-09 2001-03-13 The Regents Of The University Of California Volatile aldehydes as pest control agents
JP2000325037A (en) 1999-05-24 2000-11-28 Toppan Printing Co Ltd Antimicrobial fragrance composition
US6130196A (en) 1999-06-29 2000-10-10 Colgate-Palmolive Co. Antimicrobial multi purpose containing a cationic surfactant
DE19931185A1 (en) 1999-07-07 2001-01-18 Joerg Peter Schuer Air disinfection process
US6218336B1 (en) * 1999-10-26 2001-04-17 Applied Carbochemicals Enhanced herbicides
NL1013448C2 (en) 1999-11-01 2001-05-09 Nl I Voor Zuivelonderzoek Use of nonanoic acid as an anti-fungal agent.
DE60039783D1 (en) * 1999-12-14 2008-09-18 Genentech Inc LFA-1 ANTAGONISTS AND TNF-ALPHA ANTAGONISTS FOR
BR0108734B1 (en) 2000-02-28 2013-04-24 stabilized, concentrated, acidic antimicrobial composition, its production process, as well as method of cleaning and / or reducing microorganisms in foods.
US6852340B1 (en) * 2000-03-21 2005-02-08 Preserve International Biocide composition containing propionic acid and iodine compounds
GB0011675D0 (en) * 2000-05-15 2000-07-05 Unilever Plc Ambient stable beverage
DE60107846T3 (en) 2000-06-20 2010-11-04 Nutrition Sciences MEDIUM-CHAINED FATTY ACIDS AND THEIR USE AS ANTIMICROBIAL AGENTS
US6468953B1 (en) * 2000-08-03 2002-10-22 Lynntech, Inc. Methods of preparing antimicrobial compositions comprising ozone
US6479454B1 (en) * 2000-10-05 2002-11-12 Ecolab Inc. Antimicrobial compositions and methods containing hydrogen peroxide and octyl amine oxide
GB0027245D0 (en) 2000-11-08 2000-12-27 Saitron Ltd Powder compositions and methodology for manufacturing same
JP2002179509A (en) 2000-12-12 2002-06-26 Takasago Internatl Corp Antifugal perfume composition
CA2357265C (en) 2001-04-24 2004-04-13 University Of British Columbia Improved additive for livestock feeds
US6479044B1 (en) 2001-06-05 2002-11-12 Colgate-Palmolive Company Antibacterial solution
US7060301B2 (en) * 2001-07-13 2006-06-13 Ecolab Inc. In situ mono-or diester dicarboxylate compositions
SE0102864D0 (en) * 2001-08-29 2001-08-29 Svenska Miljoebolaget Svv Ab Antimicrorobial agent
CA2464388C (en) 2001-10-25 2010-07-06 Laboratorios Miret, S.A. Use of cationic preservative in food products
US6472358B1 (en) 2001-11-15 2002-10-29 Ecolab Inc. Acid sanitizing and cleaning compositions containing protonated carboxylic acids
AU2002351602B2 (en) 2002-01-04 2007-08-30 University Of Guelph Compositions for the preservation of fruits and vegetables
WO2003059063A1 (en) 2002-01-09 2003-07-24 Summerdale, Inc. Fungicide compositions
US20030228402A1 (en) * 2002-02-19 2003-12-11 Franklin Lanny U. Compositions and methods for preservation of food
US6475976B1 (en) 2002-02-22 2002-11-05 Colgate-Palmolive Company Antibacterial cleaning wipe comprising polyhexamethylene-4-biguanide hydrochloride
WO2003096807A1 (en) 2002-05-14 2003-11-27 Huntsman Petrochemical Corporation Agricultural formulations containing enhanced surfactants
DK200200207U3 (en) 2002-06-28 2003-10-24 Ole Kaae Hansen Holding Aps Saponin and / or sapogenin-containing plant extract
EP1662873B1 (en) * 2003-09-09 2016-01-13 3M Innovative Properties Company Antimicrobial compositions and methods
US20050161636A1 (en) * 2004-01-09 2005-07-28 Ecolab Inc. Methods for washing and processing fruits, vegetables, and other produce with medium chain peroxycarboxylic acid compositions
US7771737B2 (en) * 2004-01-09 2010-08-10 Ecolab Inc. Medium chain peroxycarboxylic acid compositions
EP1561801A1 (en) * 2004-01-28 2005-08-10 JohnsonDiversey Inc. Sanitizing and cleaning composition and its use for sanitizing and/or cleaning hard surfaces
US20050170052A1 (en) * 2004-02-02 2005-08-04 Pimentel Julio L. Water and feed preservative for animal uses
US20050260243A1 (en) * 2004-04-26 2005-11-24 The Procter & Gamble Company Method of treating microbial plant diseases
WO2006024620A1 (en) 2004-08-31 2006-03-09 Akzo Nobel N.V. Method for pigment solubilisation, a pigment composition and its use
US20100204323A1 (en) 2004-12-09 2010-08-12 The Dial Corporation Antimicrobial compositions comprising organic acid esters and methods for reducing virus and bacterial populations using such compositions
RU2288592C1 (en) 2005-06-21 2006-12-10 Государственное научное учреждение Всероссийский научно-исследовательский институт орошаемого земледелия РАСХН Green feed preservation method
CN101232823B (en) * 2005-07-25 2012-12-12 埃科莱布有限公司 Antimicrobial compositions for use on food products
US20070027119A1 (en) * 2005-07-29 2007-02-01 Ahmed Fahim U Antibacterial composition and method of use
DK2086529T3 (en) 2006-09-08 2015-05-04 Delaval Holding Ab ANTIMICROBIAL COMPOSITIONS AND RELATED APPLICATIONS
US7652067B2 (en) 2006-09-08 2010-01-26 Millenium Specialty Chemicals, Inc. Aqueous compositions containing monoester salts
RU2321273C1 (en) 2006-12-22 2008-04-10 Общество с ограниченной ответственностью "Счастливые времена" Mayonnaise
US9271494B2 (en) * 2007-08-30 2016-03-01 Ecolab USA, Inc. Shelf stable, reduced corrosion, ready to use peroxycarboxylic acid antimicrobial compositions
US7973006B2 (en) 2007-09-17 2011-07-05 Purac Biochem B.V. Antibacterial agent based on fatty acid esters of hydroxy carboxylic acid acids
EP2200457A1 (en) 2007-09-17 2010-06-30 Purac Biochem N.V. Use of fatty acid esters of glycerol combined with polylysine against gram-negative bacteria
WO2009041981A1 (en) * 2007-09-28 2009-04-02 Anitox Corporation Mold control and odor prevention in production of pelletized feedstuffs
CN101233852B (en) * 2008-03-03 2011-04-27 上海龙蟒生物科技有限公司 Fatty acid composition
US20100056413A1 (en) * 2008-09-04 2010-03-04 Harry Jr David Ray high-temperature cleaning system, associated substrates, and associated methods
PL2461700T3 (en) 2009-08-06 2016-11-30 Water and feed preservative
US20120148718A1 (en) 2009-08-31 2012-06-14 Wilson James D Method for conditioning animal feed
PL2611310T3 (en) 2010-08-27 2017-12-29 Anitox Corporation Antimicrobial formulation
PL2768539T3 (en) 2011-10-20 2017-07-31 Anitox Corporation Antimicrobial formulations with pelargonic acid
CA2848761A1 (en) 2011-11-30 2013-06-06 Anitox Corporation Antimicrobial mixture of aldehydes, organic acids and organic acid esters
CA2878936A1 (en) 2012-07-14 2014-01-23 Anitox Corporation Improved application of liquids to solid particles

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP2461700A4 *

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10785975B2 (en) 2009-08-06 2020-09-29 Anitox Corporation Water and feed antimicrobial preservative
TWI548348B (en) * 2011-10-20 2016-09-11 安麗托克斯公司 Antimicrobial formulations with pelargonic acid
CN103889464A (en) * 2011-10-20 2014-06-25 阿尼托克斯公司 Antimicrobial formulations with pelargonic acid
US10736343B2 (en) 2011-10-20 2020-08-11 Anitox Corporation Antimicrobial formulations with pelargonic acid
JP2014534967A (en) * 2011-10-20 2014-12-25 アニトックス コーポレーション Antimicrobial formulation containing pelargonic acid
WO2013059012A1 (en) 2011-10-20 2013-04-25 Anitox Corporation Antimicrobial formulations with pelargonic acid
EP2768539B1 (en) 2011-10-20 2016-12-07 Anitox Corporation Antimicrobial formulations with pelargonic acid
JP2015504312A (en) * 2011-11-30 2015-02-12 アニトックス コーポレーション Antimicrobial mixtures of aldehydes, organic acids and organic acid esters
EP2785205A4 (en) * 2011-11-30 2015-05-06 Anitox Corp Antimicrobial mixture of aldehydes, organic acids and organic acid esters
US10021901B2 (en) 2011-11-30 2018-07-17 Anitox Corporation Antimicrobial mixture of aldehydes, organic acids and fatty acid esters
CN103957732A (en) * 2011-11-30 2014-07-30 阿尼托克斯公司 Antimicrobial mixture of aldehydes, organic acids and organic acid esters
WO2013081777A1 (en) * 2011-11-30 2013-06-06 Anitox Corporation Antimicrobial mixture of aldehydes, organic acids and organic acid esters
WO2015036433A1 (en) 2013-09-13 2015-03-19 Sopura S.A. Antimicrobial composition
BE1021925B1 (en) * 2013-09-20 2016-01-27 Sopura S.A. ANTIMICROBIAL COMPOSITION.
WO2017138003A1 (en) * 2016-02-11 2017-08-17 Sharon Laboratories Ltd. Antimicrobial preservative compositions
WO2021001578A1 (en) * 2019-07-04 2021-01-07 Nutreco Ip Assets B.V. Feed additive
WO2021069572A1 (en) 2019-10-08 2021-04-15 Taminco Bvba Antimicrobial composition for animal feed
WO2021165436A1 (en) 2020-02-20 2021-08-26 Dsm Ip Assets B.V. Prevention of viral transmission through feed
WO2021214215A1 (en) * 2020-04-23 2021-10-28 Arch Uk Biocides Ltd Synergistic biocide composition with a polyglycerol ester
WO2024116186A1 (en) * 2022-11-30 2024-06-06 Adama Makhteshim Ltd. Stable allyl sulfide compositions

Also Published As

Publication number Publication date
TR201201274T1 (en) 2012-06-21
PL2461700T3 (en) 2016-11-30
RU2516279C2 (en) 2014-05-20
CL2012000181A1 (en) 2012-10-12
RU2012105054A (en) 2013-08-20
AU2010279511A1 (en) 2012-03-08
HUE028283T2 (en) 2016-12-28
JP5655075B2 (en) 2015-01-14
US20120128843A1 (en) 2012-05-24
IL217811A (en) 2014-09-30
ES2575217T3 (en) 2016-06-27
ES2618566T3 (en) 2017-06-21
UA104899C2 (en) 2014-03-25
CA2770124A1 (en) 2011-02-10
CN102469810B (en) 2013-03-20
IL217811A0 (en) 2012-03-29
JP2013501066A (en) 2013-01-10
PL3023009T3 (en) 2017-07-31
PT3023009T (en) 2017-03-13
ZA201201502B (en) 2012-11-28
CA2770124C (en) 2014-01-07
CN102469810A (en) 2012-05-23
MY174699A (en) 2020-05-08
EP3023009A1 (en) 2016-05-25
MX2012001525A (en) 2012-06-01
EP2461700A4 (en) 2014-11-05
EG26433A (en) 2013-10-27
LT3023009T (en) 2017-04-10
BR112012001880A2 (en) 2017-10-03
AU2010279511B2 (en) 2014-08-14
WO2011017367A3 (en) 2011-06-16
BR112012001880B1 (en) 2020-11-03
PT2461700E (en) 2016-06-16
HUE031547T2 (en) 2017-07-28
EP3023009B1 (en) 2016-12-07
KR101871002B1 (en) 2018-06-25
US10785975B2 (en) 2020-09-29
EP2461700A2 (en) 2012-06-13
EP2461700B1 (en) 2016-04-20
KR20120055595A (en) 2012-05-31

Similar Documents

Publication Publication Date Title
AU2010279511B2 (en) Water and feed preservative
Wales et al. Chemical treatment of animal feed and water for the control of Salmonella
EP2611310B1 (en) Antimicrobial formulation
KR20140078680A (en) Antimicrobial formulations with pelargonic acid
US20060159727A1 (en) Prevention of Systemic Microbial Infection
AU2012274978B2 (en) Glycerol compositions and solutions
TWI526157B (en) Antimicrobial formulation

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201080033914.8

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10807056

Country of ref document: EP

Kind code of ref document: A2

WWE Wipo information: entry into national phase

Ref document number: 12012500127

Country of ref document: PH

WWE Wipo information: entry into national phase

Ref document number: 2012000181

Country of ref document: CL

WWE Wipo information: entry into national phase

Ref document number: 217811

Country of ref document: IL

WWE Wipo information: entry into national phase

Ref document number: 2010807056

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 13388449

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 2012523716

Country of ref document: JP

Ref document number: 2770124

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 2012/01274

Country of ref document: TR

Ref document number: MX/A/2012/001525

Country of ref document: MX

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 1201000255

Country of ref document: TH

WWE Wipo information: entry into national phase

Ref document number: 2012105054

Country of ref document: RU

Ref document number: A201201643

Country of ref document: UA

WWE Wipo information: entry into national phase

Ref document number: 2010279511

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 389/KOLNP/2012

Country of ref document: IN

ENP Entry into the national phase

Ref document number: 20127005718

Country of ref document: KR

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 2010279511

Country of ref document: AU

Date of ref document: 20100803

Kind code of ref document: A

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112012001880

Country of ref document: BR

REG Reference to national code

Ref country code: BR

Ref legal event code: B01E

Ref document number: 112012001880

Country of ref document: BR

ENP Entry into the national phase

Ref document number: 112012001880

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20120127