DK2654455T3 - Anvendelse af organiske nitrooxymolekyler i foder for at reducere methanemission fra drøvtyggere - Google Patents

Anvendelse af organiske nitrooxymolekyler i foder for at reducere methanemission fra drøvtyggere Download PDF

Info

Publication number
DK2654455T3
DK2654455T3 DK11819164.2T DK11819164T DK2654455T3 DK 2654455 T3 DK2654455 T3 DK 2654455T3 DK 11819164 T DK11819164 T DK 11819164T DK 2654455 T3 DK2654455 T3 DK 2654455T3
Authority
DK
Denmark
Prior art keywords
nitrooxy
formula
organic molecule
methane
cyclic
Prior art date
Application number
DK11819164.2T
Other languages
English (en)
Inventor
Stephane Duval
Maik Kindermann
Original Assignee
Dsm Ip Assets Bv
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dsm Ip Assets Bv filed Critical Dsm Ip Assets Bv
Application granted granted Critical
Publication of DK2654455T3 publication Critical patent/DK2654455T3/da

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C203/00—Esters of nitric or nitrous acid
    • C07C203/02—Esters of nitric acid
    • C07C203/04—Esters of nitric acid having nitrate groups bound to acyclic carbon atoms
    • 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
    • A23K20/111—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • 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
    • A23K20/116—Heterocyclic compounds
    • A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/04—Nitro compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/075—Ethers or acetals
    • A61K31/08—Ethers or acetals acyclic, e.g. paraformaldehyde
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/275—Nitriles; Isonitriles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/345—Nitrofurans
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C207/00—Compounds containing nitroso groups bound to a carbon skeleton
    • C07C207/02—Compounds containing nitroso groups bound to a carbon skeleton the carbon skeleton not being further substituted
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C207/00—Compounds containing nitroso groups bound to a carbon skeleton
    • C07C207/04—Compounds containing nitroso groups bound to a carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/23—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
    • C07C311/24—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Polymers & Plastics (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Animal Husbandry (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Fodder In General (AREA)
  • Feed For Specific Animals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)

Claims (18)

1. Anvendelse af mindst et organisk molekyle, der er substitueret i en hvilken som helst position med mindst en nitrooxygruppe, eller et salt deraf, som defineret af formlen (I)
hvor Y er et organisk molekyle med følgende sammensætning: CaHbOdNeSg, hvor a ligger på mellem 1 og 25, b ligger på mellem 2 og 51, d ligger på mellem 0 og 8, e ligger på mellem 0 og 5, g ligger på mellem 0 og 3, som en aktiv forbindelse i dyrefoder for at reducere dannelsen af methan, som fremkommer ved drøvtyggeres fordøjelsesaktiviteter, hvor nitrooxyalkansyre, og/eller derivater deraf, som defineret af formlen (II) er udelukket,
hvor u ligger på mellem 0 og 23, og hvor carbonkæden, hvis u + 0, er en lineær, cyklisk eller forgrenet lineær eller cyklisk alifatisk carbonkæde, som kan være mono- eller polyumættet og på en hvilken som helst isomerform, Z uafhængigt er O, NH eller N-R3, hvor Z-Rl-, hvis RI + H, betegner en ester eller et sekundært amidderivat, RI uafhængigt er hydrogen eller en mættet lige, cyklisk eller forgrenet kæde af en alkyl- eller alkenylgruppe, som indeholder 1 til 10 carbonatomer, R2 uafhængigt er hydrogen eller en mættet lige eller forgrenet kæde af en alkyl- eller alkenylgruppe, som indeholder 1 til 23 carbonatomer, og R3 uafhængigt er hydrogen eller en mættet lige, cyklisk eller forgrenet kæde af en alkyl- eller alkenylgruppe, som
indeholder 1 til 10 carbonatomer.
2. Anvendelse ifølge krav 1, hvor a ligger på mellem 1 og 10, b ligger på mellem 2 og 21, d ligger på mellem 0 og 6, e ligger på mellem 0 og 3, g ligger på mellem 0 og 1.
3. Anvendelse ifølge krav 1, hvor det mindst ene organiske molekyle
med formlen (I) er en forbindelse med formlen (III), hvor n ligger på mellem 0 og 12, fortrinsvis på mellem 0 og 6, og hvor carbonkæden, hvis n + 0, er en lineær, cyklisk eller forgrenet alifatisk carbonkæde, som kan være ikke-substitueret eller substitueret med op til tre hydroxy-, alkoxy-, amino-, alkylamino-, dialkylamino- eller nitrooxygrupper, eller en mono- eller polyumættet alkenyl- eller alkynylcarbonkæde på en hvilken som helst isomerform, R4 uafhængigt er hydrogen eller en mættet lige, cyklisk eller forgrenet kæde af en alkyl- eller alkenylgruppe, som indeholder 1 til 12, fortrinsvis 1 til 6 carbonatomer. X er hydrogen, R5, R5=n, -OR5, -OCOR5, -NR5R6, -ONO2, -COOR5, -CONR5R6, -NHSO2R5 eller -SO2NHR5, R5 og R6 uafhængigt er hydrogen, lige, forgrenet eller cyklisk Cl-C12-alkylkæde, der kan være ikke-substitueret eller substitueret med op til tre hydroxy-, alkoxy-, amino-, alkylamino-, dialkylamino- eller nitrooxygrupper, mono- eller polyumættet alkenyl- eller alkynylcarbonkæde på en hvilken som helst isomerform.
4. Anvendelse ifølge et hvilket som helst af kravene 1 til 3, hvor det mindst ene organiske molekyle med formlen (I), eller et salt deraf, er valgt blandt 3-nitrooxypropanol, racemat-4-phenylbutan-l,2-diyldinitrat, 2-(hydroxymethyl)-2-
(nitrooxymethyl)-1,3-propandiol, N-ethyl-3-nitrooxy- propionsulfonylamid, 5-nitrooxy-pentannitril, 5-nitrooxy- pentan, 3-nitrooxy-propylpropionat, 1,3-bis-nitrooxypropan, 1,4-bis-nitrooxybutan, 1,5-bis-nitrooxypentan, 3-nitrooxy-propylbenzoat, 3-nitrooxy-propylhexanoat, 3-nitrooxy-propyl- 5-nitrooxy-hexanoat, benzylnitrat, isosorbid-dinitrat og N-[2-(nitrooxy)ethyl]-3-pyridincarboxamid, 2-nitro-5- nitrooxymethyl-furan og bis-(2-nitrooxyethyl)ether .
5. Anvendelse ifølge et hvilket som helst af kravene 1 til 4, hvor det mindst ene organiske molekyle med formlen (I), eller et salt deraf, er valgt blandt 3-nitrooxypropanol, 5-nitrooxy-pentannitril, 5-nitrooxy-pentan, 3-nitrooxy- propylpropionat, 1,3-bis-nitrooxypropan, 1,4-bis- nitrooxybutan, 1,5-bis-nitrooxypentan, 3-nitrooxy- propylbenzoat, 3-nitrooxy-propylhexanoat, 3-nitrooxy-propyl-5-nitrooxy-hexanoat, isosorbid-dinitrat og N-[2-(nitrooxy)ethyl]-3-pyridincarboxamid og bis-(2- nitrooxyethyl) ether.
6. Anvendelse ifølge et hvilket som helst af kravene 1 til 5, hvor det mindst ene organiske molekyle med formlen (I) er en blanding af 3-nitrooxypropanol og 1,3-bis-nitrooxypropan.
7. Anvendelse ifølge et hvilket som helst af kravene 1 til 6, hvor det mindst ene organiske molekyle med formlen (I), eller et salt deraf, kombineres med mindst et yderligere aktivt stof, der er valgt fra gruppen bestående af diallyldisulfid, hvidløgsolie, allylisothiocyanat, deoxycholsyre, chenodeoxycholsyre og derivater deraf.
8. Anvendelse ifølge et hvilket som helst af kravene 1 til 7, hvor det drøvtyggende dyr er valgt fra gruppen bestående af: kvæg, geder, får, giraffer, amerikanske bisoner, europæiske bisoner, yakokser, vandbøfler, hjorte, kameler, alpakaer, lamaer, gnuer, antiloper, gaffelbukke og nilgaiantiloper.
9. Anvendelse ifølge et hvilket som helst af kravene 1 til 8, hvor methanproduktionen hos drøvtyggere beregnet i liter pr. kilogram tørstofindtag reduceres med mindst 10 % ved måling i metaboliske kamre.
10. Anvendelse ifølge et hvilket som helst af kravene 1 til 9, hvor mængden af den mindst ene aktive forbindelse som defineret i formlen (I), der indgives til det drøvtyggende dyr, er fra 1 mg til 10 g pr. kg foder.
11. Fodersammensætning eller foderadditiv til drøvtyggere, der omfatter mindst et organisk molekyle med formlen (I) ifølge et hvilket som helst af kravene 2 til 6.
12. Fodersammensætning eller foderadditiv til drøvtyggere ifølge krav 11, der endvidere omfatter en ingrediens valgt fra gruppen bestående af calciumcarbonater, elektrolytter, proteiner, bønnekager, hvede, stivelse, solsikkekager, majs, kød- og benmel, aminosyrer, animalsk fedt, vitaminer og spormineraler.
13. Sammensætning ifølge krav 11, som er en mineralforblanding, en vitaminforblanding eller en forblanding, der indbefatter vitaminer og mineraler, eller en bolus.
14. Fremgangsmåde til reducering af produktionen af methan, som fremkommer ved drøvtyggeres fordøjelsesaktiviteter, hvilken fremgangsmåde omfatter oral indgivelse til dyret af en tilstrækkelig mængde af mindst et organisk molekyle, som er substitueret i en hvilken som helst position med mindst en nitrooxygruppe, eller et salt deraf, som defineret af formlen
forme! (!) hvor Y er et organisk molekyle med følgende sammensætning: CaHbOdNeSg, hvor a ligger på mellem 1 og 25,
b ligger på mellem 2 og 51, d ligger på mellem 0 og 8, e ligger på mellem 0 og 5, g ligger på mellem 0 og 3, hvor nitrooxyalkansyre, og/eller derivat deraf, som defineret af formlen (II) er udelukket,
forme! (I!) hvor u ligger på mellem 0 og 23, og hvor carbonkæden, hvis u + 0, er en lineær, cyklisk eller forgrenet lineær eller cyklisk alifatisk carbonkæde, som kan være mono- eller polyumættet og på en hvilken som helst isomerform, Z uafhængigt er O, NH eller N-R3, hvor Z-Rl, hvis RI + H, betegner en ester eller et sekundært amidderivat, RI uafhængigt er hydrogen eller en mættet lige, cyklisk eller forgrenet kæde af en alkyl- eller alkenylgruppe, som indeholder 1 til 10 carbonatomer, R2 uafhængigt er hydrogen eller en mættet lige eller forgrenet kæde af en alkyl- eller alkenylgruppe, som indeholder 1 til 23 carbonatomer, og R3 uafhængigt er hydrogen eller en mættet lige, cyklisk eller forgrenet kæde af en alkyl- eller alkenylgruppe, som indeholder 1 til 10 carbonatomer.
15. Fremgangsmåde ifølge krav 14, hvor det mindst ene organiske molekyle indgives til dyret i kombination med mindst et yderligere aktivt stof, der er valgt fra gruppen bestående af diallyldisulfid, hvidløgsolie, allylisothiocyanat, deoxycholsyre, chenodeoxycholsyre og derivater deraf.
16. Fremgangsmåde ifølge krav 14 eller 15, hvor det drøvtyggende dyr er valgt fra gruppen bestående af: kvæg, geder, får, giraffer, amerikanske bisoner, europæiske bisoner, yakokser, vandbøfler, hjorte, kameler, alpakaer, lamaer, gnuer, antiloper, gaffelbukke og nilgaiantiloper.
17. Fremgangsmåde ifølge et hvilket som helst af kravene 14 til 16, hvor mængden af det mindst ene organiske molekyle som defineret i formlen (I), der indgives til det drøvtyggende dyr, er fra 1 mg til 10 g pr. kg foder.
18. Fremgangsmåde ifølge et hvilket som helst af kravene 14 til 17, hvor methanproduktionen hos drøvtyggere beregnet i liter pr. kilogram tørstofindtag reduceres med mindst 10 % ved måling i metaboliske kamre.
DK11819164.2T 2010-12-20 2011-12-20 Anvendelse af organiske nitrooxymolekyler i foder for at reducere methanemission fra drøvtyggere DK2654455T3 (da)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP10195857 2010-12-20
EP11178994 2011-08-26
PCT/EP2011/072707 WO2012084629A1 (en) 2010-12-20 2011-12-20 Use of nitrooxy organic molecules in feed for reducing methane emission in ruminants, and/or to improve ruminant performance

Publications (1)

Publication Number Publication Date
DK2654455T3 true DK2654455T3 (da) 2019-02-18

Family

ID=45722564

Family Applications (1)

Application Number Title Priority Date Filing Date
DK11819164.2T DK2654455T3 (da) 2010-12-20 2011-12-20 Anvendelse af organiske nitrooxymolekyler i foder for at reducere methanemission fra drøvtyggere

Country Status (13)

Country Link
US (2) US9266814B2 (da)
EP (1) EP2654455B1 (da)
JP (1) JP5984189B2 (da)
KR (1) KR101927553B1 (da)
CN (1) CN103260424B (da)
AU (1) AU2011347802B2 (da)
BR (1) BR112013015569B1 (da)
DK (1) DK2654455T3 (da)
ES (1) ES2707876T3 (da)
NZ (1) NZ610031A (da)
PL (1) PL2654455T3 (da)
RU (1) RU2578485C2 (da)
WO (1) WO2012084629A1 (da)

Families Citing this family (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2011347802B2 (en) * 2010-12-20 2015-05-07 Dsm Ip Assets B.V. Use of nitrooxy organic molecules in feed for reducing methane emission in ruminants, and/or to improve ruminant performance
EP2713766B1 (en) 2011-05-26 2015-06-24 DSM IP Assets B.V. Use of a feed composition for reducing methane emission in ruminants, and/or to improve ruminant performance
CN103070299B (zh) * 2012-12-20 2014-05-14 西北农林科技大学 一种牦牛专用免疫营养舔砖
WO2015018726A1 (en) * 2013-08-07 2015-02-12 Dsm Ip Assets B.V. Use of a feed composition for reducing methane emission in ru-minants, and/or to improve ruminant performance
KR101656929B1 (ko) 2014-06-02 2016-09-13 씨제이제일제당 (주) 반추동물의 메탄 생성 저감용 사료 첨가제 조성물
WO2017137489A1 (en) 2016-02-12 2017-08-17 Dsm Ip Assets B.V. Anti-methanogenic compositions and uses thereof
EP3238720A1 (en) 2016-04-29 2017-11-01 DSM IP Assets B.V. Anti-methanogenic compositions and uses thereof
CN106165771A (zh) * 2016-07-20 2016-11-30 南京农业大学 2,2双甲基‑3‑(硝基氧基)丙酸的应用
CN106173339A (zh) * 2016-07-20 2016-12-07 南京农业大学 三***酯的应用
EP3541200A1 (en) * 2016-11-18 2019-09-25 DSM IP Assets B.V. Powderous formulations
US11013245B2 (en) 2017-02-14 2021-05-25 Dsm Ip Assets B.V. Water dispersible formulations
WO2018149756A1 (en) 2017-02-14 2018-08-23 Dsm Ip Assets B.V. Storage-stable formulations
WO2018153702A1 (en) * 2017-02-21 2018-08-30 Dsm Ip Assets B.V. Use of a feed composition for reducing methane emission in rumi-nants, and/or to improve ruminant performance
KR20190112329A (ko) 2017-02-21 2019-10-04 디에스엠 아이피 어셋츠 비.브이. 반추동물에서의 메탄 배출의 감소 및/또는 반추동물 성능의 개선을 위한 사료 조성물의 용도
AU2018296712B2 (en) * 2017-07-07 2023-11-02 Dsm Ip Assets B.V. Compressed tablets
EP3727356A1 (en) 2017-12-18 2020-10-28 DSM IP Assets B.V. Storage stable mixtures
US20210161849A1 (en) * 2017-12-18 2021-06-03 Dsm Ip Assets B.V. Storage stable mixtures, method of improving retention of a compound and use of rice hulls and/or rice bran to enhance retention of a compound
US20210084938A1 (en) 2017-12-18 2021-03-25 Dsm Ip Assets B.V. Storage stable mixtures
BR112020012070A2 (pt) 2017-12-18 2020-11-24 Dsm Ip Assets B.V. misturas estáveis para armazenamento
AU2018387109A1 (en) * 2017-12-18 2020-06-11 Dsm Ip Assets B.V. Storage stable mixtures
CA3087308A1 (en) 2017-12-31 2019-07-04 Dsm Ip Assets B.V. Selective production of 1,3-propanediol monoacetate
WO2019129506A1 (en) 2017-12-31 2019-07-04 Dsm Ip Assets B.V. Denitrifying enzymes
US11793768B2 (en) 2018-01-24 2023-10-24 Dsm Ip Assets B.V. Methods for the non-therapeutic alleviation or prophylaxis of symptoms of oxidative stress, reduced immune system or cartilage damage of ruminants
AU2019212738A1 (en) 2018-01-24 2020-07-23 Dsm Ip Assets B.V. Novel use
EP3784647B1 (en) 2018-04-25 2022-05-11 DSM IP Assets B.V. Novel dicarboxylic acid diesters
WO2020011992A1 (en) 2018-07-12 2020-01-16 Dsm Ip Assets B.V. Continuous production of an adsorption product of a nitrooxy-functional organic compound
ES2960721T3 (es) * 2018-09-14 2024-03-06 Dsm Ip Assets Bv Proceso de fabricación de omega nitrooxi-1-alcanoles
EP3849340B1 (en) 2018-09-14 2023-12-13 DSM IP Assets B.V. Process for the manufacture of omega nitrooxy-1-alkanols
EP3628169A1 (en) 2018-09-25 2020-04-01 DSM IP Assets B.V. 3h-1,2-dithiol-derivatives for reducing methane emission in ruminants
AU2019369157A1 (en) 2018-10-25 2021-05-06 Dsm Ip Assets B.V. Aqueous compositions comprising omega nitrooxy-1-alkanols
DK3662761T3 (da) * 2018-12-04 2021-07-26 Dsm Ip Assets Bv Opbevaringsstabile adsorbater af nitrooxyforbindelser
EP3669663A1 (en) 2018-12-17 2020-06-24 DSM IP Assets B.V. Novel beadlets
EP3718411A1 (en) 2019-04-04 2020-10-07 DSM IP Assets B.V. Novel beadlets
EP3718412A1 (en) 2019-04-04 2020-10-07 DSM IP Assets B.V. Novel beadlets
AU2020257976A1 (en) * 2019-04-16 2021-10-28 Dsm Ip Assets B.V. Early life nutrition
WO2020221805A1 (en) * 2019-04-30 2020-11-05 Dsm Ip Assets B.V. Novel fatty acid esters
WO2021116395A1 (en) 2019-12-11 2021-06-17 Dsm Ip Assets B.V. New slow-release delivery composition
WO2021116396A1 (en) 2019-12-11 2021-06-17 Dsm Ip Assets B.V. Compressed tablets
EP4140981A4 (en) 2020-04-21 2024-01-24 Kumiai Chemical Industry Co., Ltd. METHANE PRODUCTION INHIBITOR COMPOSITION AND METHOD FOR INHIBITING METHANE PRODUCTION
US20230167047A1 (en) 2020-04-22 2023-06-01 Dsm Ip Assets B.V. Process for the acylation of an alpha, omega-alkandiol
DK4037666T3 (da) 2020-12-08 2024-06-24 Ruminant Biotech Corp Ltd Forbedring af anordninger og fremgangsmåder til indgivelse af substanser til dyr
EP4323764A1 (en) 2021-04-13 2024-02-21 DSM IP Assets B.V. Method for monitoring the use of a methane inhibitor
AU2022256747A1 (en) 2021-04-15 2023-10-12 Dsm Ip Assets B.V. Use of propandiol mononitrate and limonene for reducing the formation of methane emanating and for improving the digestibility
US20240207203A1 (en) 2021-04-15 2024-06-27 Dsm Ip Assets B.V. Novel use
WO2022218967A1 (en) * 2021-04-15 2022-10-20 Dsm Ip Assets B.V. Use of gossypol and a methane inhibitor for reducing the formation of methane emanating from the digestive activities of ruminants
CN117241677A (zh) * 2021-04-15 2023-12-15 帝斯曼知识产权资产管理有限公司 新颖用途
CN113575773A (zh) * 2021-06-23 2021-11-02 中国农业科学院北京畜牧兽医研究所 用于改善反刍动物瘤胃发酵的组合物及其用途
WO2023275152A1 (en) 2021-06-29 2023-01-05 Vilofoss A/S Feed additive comprising iodoform for use in a method of reducing methane production in and/or for improving performance of a ruminant
EP4201222A1 (en) 2021-12-21 2023-06-28 Société des Produits Nestlé S.A. Combination of bornyl acetate and citral for decreasing enteric methane production in ruminants
WO2024006531A1 (en) * 2022-07-01 2024-01-04 Arkea Bio Corp. Compositions and methods for reducing deleterious atmospheric gas emissions from flooded ecosystems
KR20240070303A (ko) * 2022-11-14 2024-05-21 대한민국(농촌진흥청장) 티아민 삼인산을 포함하는 반추동물의 메탄 생성 저감용 조성물
WO2024126430A1 (en) 2022-12-14 2024-06-20 Dsm Ip Assets B.V. New method for sustainable manure management
WO2024133548A1 (en) 2022-12-21 2024-06-27 Dansk Landbrugs Grovvareselskab A.M.B.A. Method for reduction of methane production in and/or for improving performance of a ruminant

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3608087A (en) * 1968-06-21 1971-09-21 Merck & Co Inc Feed compositions
SU890961A3 (ru) * 1976-01-20 1981-12-15 Циба-Гейги Аг (Фирма) Ростстимулирующее средство дл животных
EP0223811A1 (en) 1985-05-22 1987-06-03 Beecham Group Plc Use of nicorandil or pinacidil for the treatment of peripheral vascular disease
SU1687216A1 (ru) * 1989-04-24 1991-10-30 Московская сельскохозяйственная академия им.К.А.Тимирязева Способ кормлени крупного рогатого скота
NZ242592A (en) * 1991-05-13 1993-12-23 Merck & Co Inc PROCESS FOR CONVERTING 13#a# HYDROXY AVERMECTIN AGLYCONES TO THE 13#B#
JP3232193B2 (ja) * 1994-06-02 2001-11-26 潤一 高橋 反すう動物給与用組成物及び反すう動物の飼料効率向上方法
US20050137191A1 (en) 1996-06-04 2005-06-23 Thatcher Gregory R. Nitrate esters and their use for mitigating cellular damage
KR20020042866A (ko) * 1999-10-14 2002-06-07 마크 제이. 건더슨 반추 동물에서 메탄 생성의 상승효과적 감소를 위한폴리시클릭 퀴논 및 이오노포어 조성물
JP4783512B2 (ja) * 2001-03-27 2011-09-28 社団法人農林水産先端技術産業振興センター 反芻動物のメタン生成を抑制する飼料組成物
JP3680167B2 (ja) * 2001-07-11 2005-08-10 エーザイ株式会社 味識別装置及び識別方法
JP5192108B2 (ja) * 2001-09-19 2013-05-08 株式会社ヤクルト本社 反芻動物用のメタン生成抑制用組成物及び飼料用組成物
CA2611140C (en) 2005-06-09 2013-11-19 University Of Manitoba Compositions and methods for enhancing nitric oxide delivery
US20070098796A1 (en) * 2005-10-31 2007-05-03 Rekhi Gurvinder S Controlled release compositions comprising a combination of isosorbide dinitrate and hydralazine hydrochrloride
WO2009007230A1 (en) 2007-07-09 2009-01-15 Nicox S.A. Use of nitric oxide releasing compounds in the treatment of chronic pain
ES2332859B1 (es) 2008-06-12 2010-09-22 Carotenoid Technologies, S.A. Procedimiento para mejorar el estado general de los rumiantes.
FR2933191B1 (fr) 2008-06-25 2010-06-25 Valorisation Par Extrusion Procede d'evaluation de la quantite de methane produite par un ruminant laitier et procede pour diminuer et controler cette quantite.
WO2010072584A1 (en) 2008-12-23 2010-07-01 Dsm Ip Assets B.V. Bile acids in feed for reducing methane production emanating from the digestive activities of ruminants
JP2010200730A (ja) * 2009-02-27 2010-09-16 Ajinomoto Co Inc 反芻動物用のメタン生成抑制剤および飼料組成物
CN101611762B (zh) * 2009-07-23 2011-12-28 中国农业大学 一种复合产甲烷速效抑制剂及其制备方法和用途
UY32802A (es) 2009-07-23 2011-01-31 Provimi Holding B V Composiciones para reducir la metanogénesis gastrointestinal en rumiantes
AU2011347802B2 (en) * 2010-12-20 2015-05-07 Dsm Ip Assets B.V. Use of nitrooxy organic molecules in feed for reducing methane emission in ruminants, and/or to improve ruminant performance
EP2713766B1 (en) * 2011-05-26 2015-06-24 DSM IP Assets B.V. Use of a feed composition for reducing methane emission in ruminants, and/or to improve ruminant performance

Also Published As

Publication number Publication date
US20140147529A1 (en) 2014-05-29
CN103260424B (zh) 2016-05-11
BR112013015569B1 (pt) 2020-03-03
US9266814B2 (en) 2016-02-23
PL2654455T3 (pl) 2019-05-31
KR101927553B1 (ko) 2018-12-10
CN103260424A (zh) 2013-08-21
BR112013015569A2 (pt) 2016-07-19
ES2707876T3 (es) 2019-04-05
JP5984189B2 (ja) 2016-09-06
US9902685B2 (en) 2018-02-27
AU2011347802B2 (en) 2015-05-07
AU2011347802A8 (en) 2013-06-06
NZ610031A (en) 2015-01-30
RU2578485C2 (ru) 2016-03-27
AU2011347802A1 (en) 2013-05-09
RU2013133968A (ru) 2015-01-27
EP2654455A1 (en) 2013-10-30
EP2654455B1 (en) 2018-10-24
WO2012084629A1 (en) 2012-06-28
US20150376113A1 (en) 2015-12-31
JP2013545485A (ja) 2013-12-26
KR20130126642A (ko) 2013-11-20

Similar Documents

Publication Publication Date Title
DK2654455T3 (da) Anvendelse af organiske nitrooxymolekyler i foder for at reducere methanemission fra drøvtyggere
DK2713766T3 (da) Anvendelse af en fodersammensætning til reduktion af methanudslip fra drøvtyggere og/eller til forbedring af drøvtyggerfunktionen
EP2509435B1 (en) Nitrooxy alkanoic acids and derivatives thereof in feed for reducing methane emission in ruminants, and/or to improve ruminant performance
AU2012260799A1 (en) Use of a feed composition for reducing methane emission in ruminants, and/or to improve ruminant performance
EP3041365B1 (en) Use of a feed composition for reducing methane emission in ru-minants, and/or to improve ruminant performance
EP2830434B1 (en) Use of para nitro amino derivatives in feed for reducing me-thane emission in ruminants
NZ617849B2 (en) Use of a feed composition for reducing methane emission in ruminants, and/or to improve ruminant performance