WO2011045418A1 - Acides azidoalcanoïques et leurs dérivés dans l'alimentation pour réduire une émanation de formation de méthane à partir des activités digestives de ruminants - Google Patents

Acides azidoalcanoïques et leurs dérivés dans l'alimentation pour réduire une émanation de formation de méthane à partir des activités digestives de ruminants Download PDF

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Publication number
WO2011045418A1
WO2011045418A1 PCT/EP2010/065533 EP2010065533W WO2011045418A1 WO 2011045418 A1 WO2011045418 A1 WO 2011045418A1 EP 2010065533 W EP2010065533 W EP 2010065533W WO 2011045418 A1 WO2011045418 A1 WO 2011045418A1
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azido
ethyl
acid
feed
use according
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PCT/EP2010/065533
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English (en)
Inventor
Stephane Duval
Maik Kindermann
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Dsm Ip Assets B.V.
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Publication of WO2011045418A1 publication Critical patent/WO2011045418A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/105—Aliphatic or alicyclic compounds
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
    • Y02P60/20—Reduction of greenhouse gas [GHG] emissions in agriculture, e.g. CO2
    • Y02P60/22—Methane [CH4], e.g. from rice paddies

Definitions

  • the present invention relates to the use of at least one azido alkanoic acid and/or derivative thereof for reducing the production of methane emanating from the digestive activities of ruminants.
  • the present invention also relates to animal feed or animal feed composition and feed additives comprising these active compounds.
  • feed or feed composi- tion means any compound, preparation, mixture, or composition suitable for, or intended for intake by an animal.
  • a ruminant is a mammal of the order Artiodactyla that digests plant-based food by initially softening it within the animal's first stomach, known as the rumen, then regurgitating the semi-digested mass, now known as cud, and chewing it again.
  • the process of again chewing the cud to further break down plant matter and stimulate digestion is called "ruminating". Ruminating mammals include cattle, goats, sheep, giraffes, American Bison, European bison, yaks, water buffalo, deer, camels, alpacas, llamas, wildebeest, antelope, pronghorn, and nilgai.
  • domestic cattle are the most preferred species.
  • the term includes all races of domestic cattle, and all production kinds of cattle, in particular dairy cows and beef cattle.
  • Rumen fermentation brings some disadvantages. Methane is produced as a natural consequence of the anaerobic fermentation, which represents an energy loss to the host animal. Carbohydrate makes up 70 to 80 % of the dry matter in a typical dairy cattle ration and in spite of this the absorption of carbohydrates from the gastrointestinal tract is normally very limited. The reason for this is the extensive fermentation of carbohydrates in the rumen resulting in production of acetate, propionate and butyrate as the main products. These products are part of the so called volatile fatty acids, VFA.
  • methane is also a greenhouse gas, which is many times more potent than CO2. Its concentration in the atmosphere has doubled over the last century and continues to increase alarmingly. Ruminants are the major contributors to the biogenic methane formation, and it has been estimated that the prevention of methane formation from ruminants would almost stabilize atmospheric methane concentrations. Furthermore, the assessment of the Kyoto protocol places increased priority in decreasing methane emissions as part of a multi-gas strategy. The most effective additives currently used for reducing the formation of methane contain antibiotics which diminish the proliferation of microorganisms providing hydrogen (H 2 ) to the methanogenes. However, the effect of antibiotics on the formation of methane has some disadvantages because of rapid adaptation of the microflora and/or resistance development leading to a complete loss of the intended effect.
  • the present inventors surprisingly found that the compounds specified herein after have a great potential for use in animal feed in order to essentially reduce the for- mation of methane without affecting microbial fermentation in a way that would be detrimental to the host animal.
  • the present invention provides the use of at least one azido alkanoic acid and/or derivative thereof for suppressing methane formation in ruminants.
  • the invention further provides a method for reducing the production of methane emanating from the digestive activities of ruminants comprising orally administering a sufficient amount of at least one azido alkanoic acid and/or derivative thereof to the animal.
  • Azido alkanoic acids and/or derivatives thereof according to the invention are defined by the following formula (I)
  • n signifies 0,1 , 2, 3, 4, or 5, preferably 0, 1 , 2 or 3
  • X is independently O or NH, wherein if R1 ⁇ H, X-R1 - represents an ester or a secondary amide group of the compound,
  • R1 is independently, hydrogen or a saturated straight or branched chain of an al- kyl or alkenyl group containing 1 to 10, preferably 1 to 8 carbon atoms
  • R2 is independently, hydrogen or a saturated straight or branched chain of an alkyi or alkenyl group containing 1 to 8, preferably 1 to 3 carbon atoms.
  • a preferred alkyl group is methyl, ethyl, propyl, isopropyl, butyl, sec. butyl, isobutyl, pentyl, neopentyl, hexyl, 2- ethyl-hexyl and octyl.
  • any alkyl or alkenyl group containing three or more carbon atoms can be straight chain or branched.
  • preferred esters according to the present invention are methyl, ethyl, propyl, isopropyl, butyl, sec. butyl, isobutyl, pentyl, neopentyl, hexyl, 2- ethyl-hexyl and octyl.
  • preferred amide derivatives are ethyl-amides, pro- pyl-amides, butyl-amides and pentyl-amides.
  • More preferred compounds of formula (I) in accordance with the present invention are compounds in which the R2 group is a hydrogen. These compounds comprise the following azido alkanoic acids, and esters thereof: 2-azido ethanonic acid, 3- azido propionic acid, 4-azido butanoic acid, 5-azido pentanoic acid, ethyl-2-azido ethanonate, ethyl-3-azido propionate, ethyl-4-azido butanoate, and ethyl-5-azido pentanoate.
  • preferred amide derivatives according to the present invention are 2-azido-N-ethyl ethanoic-amide, 3-azido-N- ethyl-propionic amide, 4-azido-N-ethyl-butanoic amide and 5-azido-N-ethyl- pentanoic amide.
  • the compounds 4-azido butanoic acid, 5- azido pentanoic acid, ethyl-3-azido propionate, ethyl-4-azido butanoate, and ethyl-5-azido pentanoate which are disclosed in table 1 , are especially preferred compounds in view of their properties in decreasing methane formation.
  • more preferred compounds of formula (I) in accordance with the present invention are compounds in which the R2 group is a methyl, ethyl, propyl, or isopropyl.
  • These compounds comprise the following azido alkanoic acids, and esters thereof: 2-azido propionic acid, 2-azido butanoic acid, 2-azido pentanoic acid, 2-azido-2-isopropyl ethanoic acid, 3-azido butanoic acid, 3-azido pentanoic acid, 3-azido n-hexanoic acid, 3-azido-3-isopropyl propanoic acid, 4-azido pentanoic acid, ethyl-2-azido propionate, ethyl-2-azido butanoate, ethyl-2-azido pentanoate, ethyl-2-azido-2-isopropy
  • preferred amides according to the present invention are 2-azido-N-ethyl propionic-amide, 2-azido-N-ethyl-butanoic amide, 3-azido-N-ethyl-butanoic amide and 4-azido-N-ethyl-pentanoic amide.
  • the term "a derivative thereof as herein also comprises salts of the azido alkanoic acids.
  • Preferred cations for salt preparation may be selected from the group consisting of sodium (Na+), potassium (K+), lithium (Li+), magnesium (Mg2+), calcium (Ca2+), barium (Ba2+), strontium (Sr2+), and ammonium (NH4+). Salts may also be prepared from an alkali metal or an alkaline earth metal.
  • the compounds of the present invention can be manufactured in principle according to synthetic methods known per se for azido alkanoic acids, and derivatives thereof.
  • the reaction is generally conducted as described in examples 1 to 3.
  • the product i.e. the compound of formula I
  • the product can be isolated and purified by methods known per se, e.g. by adding a solvent such as diethyl-ether or ethyl acetate to induce the separation of the crude product from the mixture after re- action, and drying over Na 2 SO 4 of the collected crude product.
  • a solvent such as diethyl-ether or ethyl acetate
  • the compounds of the present invention are useful as compounds for feed additives and animal feed compositions for ruminants, and accordingly are useful as the active ingredients in such feed to reduce methane formation in the digestive tract of the animal.
  • the compounds may be incorporated in the feed by methods known per se in the art of feed formulation and processing. Further aspects of the present invention are therefore formulations, i.e. feed additives and animal feed compositions containing compounds as herein above defined.
  • the normal daily dosage of a compound according to the invention provided to an animal by feed intake depends upon the kind of animal and its condition. Normally this dosage should be in the range of from about 50 to about 1000 mg, preferably from about 100 to about 500 mg compound per kg of feed.
  • azido alkanoic acids and derivatives thereof need not be that pure; it may e.g. include other compounds and derivatives.
  • the at least one azido alkanoic acid and/or derivative thereof may be used in combination with conventional ingredients present in an animal feed composition (diet) such as calcium carbonates, electrolytes such as ammonium chloride, proteins such as soya bean meal, wheat, starch, sunflower meal, corn, meat and bone meal, amino acids, animal fat, vitamins and trace minerals.
  • animal feed composition such as calcium carbonates, electrolytes such as ammonium chloride, proteins such as soya bean meal, wheat, starch, sunflower meal, corn, meat and bone meal, amino acids, animal fat, vitamins and trace minerals.
  • compositions of the invention are the following:
  • An animal feed additive comprising (a) at least one compound selected from table 1 (b) at least one fat-soluble vitamin, (c) at least one water-soluble vitamin, (d) at least one trace mineral, and/or (e) at least one macro mineral;
  • An animal feed composition comprising at least one compound selected from table 1 and a crude protein content of 50 to 800 g/kg feed.
  • premixes are examples of animal feed additives of the invention.
  • a premix designates a preferably uniform mixture of one or more micro-ingredients with diluent and/or carrier. Premixes are used to facilitate uniform dispersion of micro-ingredients in a larger mix.
  • the premix of the invention contains at least one fat-soluble vitamin, and/or at least one water soluble vitamin, and/or at least one trace mineral, and/or at least one macro mineral.
  • the premix of the invention comprises the at least one compound according to the invention together with at least one additional component selected from the group consisting of fat-soluble vitamins, water-soluble vitamins, trace minerals, and macro minerals. Macro minerals may be separately added to the feed. Therefore, in a particular embodiment, the premix comprises the active ingredients of the invention together with at least one additional component selected from the group consisting of fat- soluble vitamins, water-soluble vitamins, and trace-minerals.
  • the premix comprises the active ingredients of the invention together with at least one additional component selected from the group consist
  • fat-soluble vitamins are vitamin A, vitamin D3, vitamin E, and vitamin K, e.g. vitamin K3.
  • water-soluble vitamins are vitamin B12, biotin and choline, vitamin B1 , vitamin B2, vitamin B6, niacin, folic acid and panthothenate, e.g. Ca-D- panthothenate.
  • trace minerals are manganese, zinc, iron, copper, iodine, selenium, and cobalt.
  • macro minerals are calcium, phosphorus and sodium.
  • the ruminant diet is usually composed of an easily degradable fraction (named concentrate) and a fibre-rich less readily degradable fraction (named hay, forage, or roughage).
  • Hay is made of dried grass, legume or whole cereals.
  • Grasses include among others timothy, ryegrasses, fescues.
  • Legumes include among others clover, lucerne or alfalfa, peas, beans and vetches.
  • Whole cereals include among others barley, maize (corn), oat, sorghum.
  • Forage crops include sugarcane, kales, rapes, and cabbages.
  • root crops such as turnips, swedes, alias, fodder beet, and sugar beet (including sugar beet pulp and beet molasses) are used to feed ruminants.
  • tubers such as potatoes, cassava and sweet potato.
  • Silage is an ensiled version of the fibre-rich fraction (e.g. from grasses, legumes or whole cereals) whereby material with a high water content is treated with a controlled anaerobic fermentation process (naturally-fermented or additive treated).
  • Concentrate is largely made up of cereals (such as barley including brewers grain and distillers grain, maize, wheat, sorghum), but also often contain protein-rich feed ingredients such as soybean, rapeseed, palm kernel, cotton seed and sunflower.
  • Cows may also be fed total mixed rations (TMR), where all the dietary components, e.g. forage, silage and concentrate, are mixed before serving.
  • TMR total mixed rations
  • a premix is an example of a feed additive which may comprise the active compounds according to the invention. It is understood that the compounds may be administered to the animal in different other forms. For example the compounds can also be included in a bolus that would be placed in the rumen and that would release a defined amount of the active compounds continuously in well defined dosages over a specific period of time.
  • the present invention also relates to the use of azido alkanoic acids and derivatives thereof in combination with at least one additional active substance which shows similar effects with regard to methane formation in the rumen and which is selected from the group consisting of diallyl disulfide, garlic oil, allyl isothiocyanate, deoxy- cholic acid, chenodeoxycholic acid and derivatives thereof.
  • yeasts and ionophores like Monensin, Rumensin.
  • diallyl disulfide, garlic oil, allyl isothiocyanate deoxycholic acid, chenodeoxycholic acid and derivatives thereof are independently administered in dosage ranges of for example 0.01 -500 mg active substance per kg feed (ppm).
  • ppm active substance per kg feed
  • Feed is given into a syringe with a composition of rumen liquor and an appropriate mixture of buffers.
  • the solution is incubated at 39 °C. After 24 hours the quantity (and composition) of methane produced is measured and put into a formula for conversion.
  • the feed stuff is sieved to 1 mm - usually TMR (44 % concentrate, 6 % hay, 37 % maize silage and 13 % grass silage) - and weighed exactly into 64 syringes.
  • 4 of these syringes are the substrate controls, which display the gas production without the effect of the tested compounds.
  • 4 other syringes are positive control, in which bromoethane sulfonate has been added to 0.1 mM.
  • 4 syringes contain a carrier control (if the test compounds need a carrier).
  • the remaining syringes contain the test substances, by groups of 4 syringes.
  • the components are mixed in a Woulff bottle in following order:
  • the completed solution is warmed up to 39 °C followed by the addition of 1 .83 ml sodium salt solution and the addition of reduction solution at 36 °C.
  • the rumen liquor is added, when the indicator turns colourless. Extraction of the rumen liquor:
  • the diluted rumen fluid (24 ml) is added to the glass syringe.
  • the syringes are then incubated for 8 hours at 39 °C under gentle agitation. After 8 hours, the volume of gas produced is measured, and the percentage of methane in the gas phase is determined by gas chromatography.
  • the food fermented was artificial TMR (44 % concentrate, 6 % hay, 37 % maize silage and 13 % grass silage).
  • Example 1 Effect of ethyl-3-azido propionate in an in vitro continuous rumen simulation system: "Rusitec”. In vitro system and experimental diets:
  • NDF Neutral detergent fibre
  • the fermenters were filled with 100 ml pre-warmed buffer and 900 ml strained ruminal fluid. Thereafter, two nylon bags were administered whereby the first one was filled with solid ruminal content (about 40 g fresh matter) and the second one with the respective experimental diet. On the second experimental day the bag containing the solid ruminal content was exchanged with another bag contain- ing the experimental diet. Each feed bag was incubated for 48 h. To maintain an- aerobic conditions the system was flushed with gaseous nitrogen for 3 min after exchanging the feed bags. The incubation temperature was kept constant at 39.5 °C.
  • Buffer flow to the fermenters was continuous and averaged 397 ml/d, resulting in a dilution rate of about 40 % per day.
  • the resulting incubation fluid outflow was col- lected in bottles chilled at -20 °C.
  • Incubation fluid samples collected directly from the fermenters via a three-way valve using a syringe equipped with a plastic tube 3 hours before exchanging the feed bags, were analysed daily for redox potential and pH using the respective electrodes connected to a pH meter (model 634; Methrom AG, Herisau, Switzerland).
  • the fermentation gases produced during 24 h were collected in gas-tight aluminium bags (TECOBAG 8 litres, PETP/AL/ PE - 12/12/75 quality; Tesserau Container GmbH, Burstadt, Germany). Gas was analysed daily for concentrations of CH , CO2 and H 2 with a GC (model 5890 Series II; Hewlett Packard, Avondale, PA, USA) equipped with a flame ionisation detector (to determine CH ), a thermal conductivity detector (to determine CO2 and H 2 ) and a 2-34m x 2-3mm column, 80/100 mesh (Porapak Q; Fluka Chemie AG, Buchs, Switzerland). The total amount of gas produced was quantified by water displacement.
  • Entodiniomorphs (x10 3 /ml) 2.37 7.75 0.603

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  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Animal Husbandry (AREA)
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Abstract

La présente invention porte sur un procédé de réduction de la production de méthane émanant des activités digestives d'un ruminant, à l'aide, comme composé actif, d'au moins un acide azidoalcanoïque et/ou d'un dérivé de celui-ci, qui est administré à l'animal conjointement avec l'alimentation. L'invention porte également sur l'utilisation de ces ingrédients dans l'alimentation pour animal et les additifs d'aliment pour animaux tels que des prémélanges, des concentrés et une ration totale mélangée (TMR) ou sous la forme d'un bolus.
PCT/EP2010/065533 2009-10-16 2010-10-15 Acides azidoalcanoïques et leurs dérivés dans l'alimentation pour réduire une émanation de formation de méthane à partir des activités digestives de ruminants WO2011045418A1 (fr)

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EP09013129.3 2009-10-16

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2644038A1 (fr) * 2012-03-26 2013-10-02 DSM IP Assets B.V. Utilisation de dérivés para nitro aminés dans des aliments pour réduire l'émission de méthane chez les ruminants
CN103518965A (zh) * 2013-10-11 2014-01-22 中国农业科学院饲料研究所 可降低牛羊甲烷排放量的预混合饲料
JP2014515930A (ja) * 2011-05-26 2014-07-07 ディーエスエム アイピー アセッツ ビー．ブイ． 反芻動物のメタン排出を低減するため、および／または反芻動物の能力を改善するための飼料組成物の使用
JP2016526917A (ja) * 2013-08-07 2016-09-08 ディーエスエム アイピー アセッツ ビー．ブイ． 反芻動物からのメタン排出を削減するため、および／または反芻動物のパフォーマンスを改善するための飼料組成物の使用
US11191288B2 (en) * 2017-02-21 2021-12-07 Dsm Ip Assets B.V. Use of a feed composition for reducing methane emission in ruminants, and/or to improve ruminant performance

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014515930A (ja) * 2011-05-26 2014-07-07 ディーエスエム アイピー アセッツ ビー．ブイ． 反芻動物のメタン排出を低減するため、および／または反芻動物の能力を改善するための飼料組成物の使用
US20170105958A1 (en) * 2011-05-26 2017-04-20 Dsm Ip Assets B.V. Use of a feed composition for reducing methane emission in ruminants, and/or to improve ruminant performance
US10154981B2 (en) 2011-05-26 2018-12-18 Dsm Ip Assets B.V. Use of a feed composition for reducing methane emission in ruminants, and/or to improve ruminant performance
EP2644038A1 (fr) * 2012-03-26 2013-10-02 DSM IP Assets B.V. Utilisation de dérivés para nitro aminés dans des aliments pour réduire l'émission de méthane chez les ruminants
WO2013144786A1 (fr) * 2012-03-26 2013-10-03 Dsm Ip Assets B.V. Utilisation de dérivés de para nitro amino dans l'alimentation pour réduire les émissions de méthane chez les ruminants
RU2615390C2 (ru) * 2012-03-26 2017-04-04 ДСМ АйПи АССЕТС Б.В. Применение пара-нитроаминопроизводных в корме для снижения выделения метана у жвачных животных
JP2016526917A (ja) * 2013-08-07 2016-09-08 ディーエスエム アイピー アセッツ ビー．ブイ． 反芻動物からのメタン排出を削減するため、および／または反芻動物のパフォーマンスを改善するための飼料組成物の使用
CN103518965A (zh) * 2013-10-11 2014-01-22 中国农业科学院饲料研究所 可降低牛羊甲烷排放量的预混合饲料
CN103518965B (zh) * 2013-10-11 2015-04-01 中国农业科学院饲料研究所 可降低牛羊甲烷排放量的预混合饲料
US11191288B2 (en) * 2017-02-21 2021-12-07 Dsm Ip Assets B.V. Use of a feed composition for reducing methane emission in ruminants, and/or to improve ruminant performance

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