Nitrooxy alkanoic acids and derivatives thereof in feed for reducing methane emission in ruminants, and/or to improve ruminant performance

Patent metadata

Field	Value
Publication number	US-9365489-B2
Application number	US-201414159576-A
Country	US
Kind code	B2
Filing date	Jan 21, 2014
Priority date	Dec 11, 2009
Publication date	Jun 14, 2016
Grant date	Jun 14, 2016

Abstract

The present invention relates to a method for reducing the production of methane emanating from the digestive activities of a ruminant and or for improving ruminant animal performance by using, as active compound at least one nitrooxy alkanoic acid and/or derivative thereof, which is administrated to the animal together with the feed. The invention also relates to the use of these compounds in feed and feed additives such as premix, concentrates and total mixed ration (TMR) or in the form of a bolus.

First claim

The invention claimed is:

1. A feed composition or feed additive comprising at least one nitrooxy alkanoic acid and derivative thereof as defined by formula (I);

as an active compound in the animal feed composition or feed additive for reducing the formation of methane emanating from the digestive activities of ruminants, and/or for improving ruminant performance, wherein
n is a number between 0 and 23 and, wherein if n≈0, then the carbon chain is a linear, a cyclic, or branched linear or cyclic aliphatic carbon chain which may be mono- or polyunsaturated and in any isomeric form,
X is independently O, NH, or N—R3, wherein if R1≠H, then X—R1-represents an ester or a secondary amide derivative,
R1 is independently, hydrogen or a saturated straight, cyclic or branched chain of an alkyl or alkenyl group containing 1 to 10 carbon atoms,
R2 is independently, hydrogen or a saturated straight or branched chain of an alkyl or alkenyl group containing 1 to 23 carbon atoms, and
R3 is independently, hydrogen or a saturated straight, cyclic or branched chain of an alkyl or alkenyl group containing 1 to 10 carbon atoms, and wherein
the feed composition or feed additive is a mineral premix, a vitamin premix, or a premix including vitamins and minerals.

2. The feed composition or feed additive of claim 1 , wherein
n is a number between 0 and 9, and wherein, if n≠0, then the carbon chain is a linear, a cyclic, or branched linear or cyclic aliphatic carbon chain in any isomeric form,
X is independently O, NH, or N—R3, wherein if R1≠H, then X—R1-represents an ester or a secondary amide derivative,
R1 is independently, hydrogen or a saturated straight or branched chain of an alkyl or alkenyl group containing 1 to 5 carbon atoms,
R2 is independently, hydrogen or a saturated straight or branched chain of an alkyl or alkenyl group containing 1 to 9 carbon atoms, and
R3 is independently, hydrogen or a saturated straight or branched chain of an alkyl or alkenyl group containing 1 to 5 carbon atoms.

3. The feed composition or feed additive of claim 1 , wherein
R1 is selected from the group consisting of hydrogen (H), methyl, and ethyl,
R2 is independently selected from the group consisting of hydrogen (H), methyl, and ethyl,
R3 is independently selected from the group consisting of hydrogen (H), methyl, and ethyl.

4. The feed composition or feed additive of claim 1 , wherein
R1 is selected from the group consisting of hydrogen (H), methyl, and ethyl,
R2 is a hydrogen (H),
R3 is independently selected from the group consisting of hydrogen (H), methyl, and ethyl.

5. The feed composition or feed additive of claim 1 , wherein
X is oxygen (O), wherein if R1≠H, then X—R1- represents an ester, and
R2 is a hydrogen (H).

6. A feed composition or feed additive comprising at least one nitrooxy alkanoic acid and/or derivative thereof which is selected from the group consisting of 3-nitrooxy propionic acid, methyl-3-nitrooxy propionate, ethyl-3-nitrooxy propionate, ethyl-4-nitrooxy-butanoate, ethyl-3-nitrooxy-butanoate, 5-nitrooxy pentanoic acid, ethyl-5-nitrooxy pentanoate, 6-nitrooxy hexanoic acid, ethyl-6-nitrooxy hexanoate, ethyl-4-nitrooxy-cyclohexylcarboxylate, 8-nitrooxy octanoic acid, ethyl-8-nitrooxy octanoate, 11-nitrooxy undecanoic acid, ethyl-11-nitrooxy undecanoate, 5-nitrooxy-N-pentanoic amide, and 5-nitrooxy-N-methyl-pentanoic amide.

7. The feed composition or feed additive of claim 6 , which further comprises at least one additional active substance selected from the group consisting of diallyl disulfide, garlic oil, allyl isothiocyanate, deoxycholic acid, chenodeoxycholic acid and derivatives thereof.

8. The feed composition or feed additive of claim 1 , wherein the ruminant animal is selected from the group consisting of: cattle, goats, sheep, giraffes, American Bison, European bison, yaks, water buffalo, deer, camels, alpacas, llamas, wildebeest, antelope, pronghorn, and nilgai.

9. The feed composition or feed additive of claim 1 , wherein the at least one active compound is present in an amount sufficient to reduce methane production in ruminants calculated in liters per kilogram of dry matter intake by at least 10% when measured in metabolic chambers.

10. The feed composition or feed additive of claim 1 , wherein the at least one active compound is present in an amount from 1 mg to 10 g per kg feed.

11. The feed composition or feed additive of claim 1 , wherein R1 is a saturated straight, cyclic or branched chain of an alkyl or alkenyl group containing 1 to 5 carbon atoms.

12. The feed composition or feed additive of claim 1 , wherein R2 is a saturated straight, cyclic or branched chain of an alkyl or alkenyl group group containing 1 to 9 carbon atoms.

13. The feed composition or feed additive of claim 1 , wherein R3 is a saturated straight, cyclic or branched chain of an alkyl or alkenyl group group containing 1 to 5 carbon atoms.

14. A feed composition or feed additive comprising at least one nitrooxy alkanoic acid and derivative thereof as defined by formula (I):

as an active compound in the animal feed composition or feed additive for reducing the formation of methane emanating from the digestive activities of ruminants, and/or for improving ruminant performance, wherein
n is a number between 0 and 23 and, wherein if n≠0, then the carbon chain is a linear, a cyclic, or branched linear or cyclic aliphatic carbon chain which may be mono- or polyunsaturated and in any isomeric form,
X is independently O, NH, or N—R3, wherein if R1≠H, then X—R1-represents an ester or a secondary amide derivative,
R1 is independently, hydrogen or a saturated straight, cyclic or branched chain of an alkyl or alkenyl group containing 1 to 10 carbon atoms,
R2 is independently, hydrogen or a saturated straight or branched chain of an alkyl or alkenyl group containing 1 to 23 carbon atoms, and
R3 is independently, hydrogen or a saturated straight, cyclic or branched chain of an alkyl or alkenyl group containing 1 to 10 carbon atoms, and wherein
the feed composition or feed additive further comprises at least one additional active substance selected from the group consisting of diallyl disulfide, garlic oil, allyl isothiocyanate, deoxycholic acid, chenodeoxycholic acid and derivatives thereof.

Assignees

• Dsm Ip Assets Bv

Inventors

• Duval Stephane
• Kindermann Maik

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P3/00

  Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00) · CPC title

• A61P3/02

  Nutrients, e.g. vitamins, minerals · CPC title

• C07C203/04 Primary

  having nitrate groups bound to acyclic carbon atoms · CPC title

• A23K50/10 Primary

  for ruminants · CPC title