WO2024126430A1 - New method for sustainable manure management - Google Patents
New method for sustainable manure management Download PDFInfo
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- WO2024126430A1 WO2024126430A1 PCT/EP2023/085221 EP2023085221W WO2024126430A1 WO 2024126430 A1 WO2024126430 A1 WO 2024126430A1 EP 2023085221 W EP2023085221 W EP 2023085221W WO 2024126430 A1 WO2024126430 A1 WO 2024126430A1
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- Prior art keywords
- nitrooxy
- manure
- comprised
- animal
- bis
- Prior art date
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- 239000010871 livestock manure Substances 0.000 title claims abstract description 33
- 210000003608 fece Anatomy 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 11
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 44
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- -1 nitrooxy organic compound Chemical class 0.000 claims abstract description 10
- 239000002002 slurry Substances 0.000 claims abstract description 10
- 244000144972 livestock Species 0.000 claims abstract description 7
- 241000282898 Sus scrofa Species 0.000 claims abstract description 6
- 241001465754 Metazoa Species 0.000 claims description 17
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 claims description 13
- PTMLFFXFTRSBJW-UHFFFAOYSA-N 3-hydroxypropyl nitrate Chemical compound OCCCO[N+]([O-])=O PTMLFFXFTRSBJW-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- 241000287828 Gallus gallus Species 0.000 claims description 4
- 241000282887 Suidae Species 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- IZUDEUAXDJRXOA-UHFFFAOYSA-N (5-nitrofuran-2-yl)methyl nitrate Chemical compound [O-][N+](=O)OCC1=CC=C([N+]([O-])=O)O1 IZUDEUAXDJRXOA-UHFFFAOYSA-N 0.000 claims description 2
- ZJQALFNKACFZLG-UHFFFAOYSA-N 3-nitrooxypropyl 5-nitrooxyhexanoate Chemical compound [O-][N+](=O)OC(C)CCCC(=O)OCCCO[N+]([O-])=O ZJQALFNKACFZLG-UHFFFAOYSA-N 0.000 claims description 2
- SDZZXXPQUWQAAG-UHFFFAOYSA-N 3-nitrooxypropyl benzoate Chemical compound [O-][N+](=O)OCCCOC(=O)C1=CC=CC=C1 SDZZXXPQUWQAAG-UHFFFAOYSA-N 0.000 claims description 2
- ZJGPXHOHSQJTSR-UHFFFAOYSA-N 3-nitrooxypropyl hexanoate Chemical compound CCCCCC(=O)OCCCO[N+]([O-])=O ZJGPXHOHSQJTSR-UHFFFAOYSA-N 0.000 claims description 2
- KOSAMXZBGUIISK-UHFFFAOYSA-N 3-nitrooxypropyl nitrate Chemical compound [O-][N+](=O)OCCCO[N+]([O-])=O KOSAMXZBGUIISK-UHFFFAOYSA-N 0.000 claims description 2
- WFBIGGUXTFTIOF-UHFFFAOYSA-N 3-nitrooxypropyl propanoate Chemical compound CCC(=O)OCCCO[N+]([O-])=O WFBIGGUXTFTIOF-UHFFFAOYSA-N 0.000 claims description 2
- UCGQVEKERMOHEL-UHFFFAOYSA-N 4-cyanobutyl nitrate Chemical compound [O-][N+](=O)OCCCCC#N UCGQVEKERMOHEL-UHFFFAOYSA-N 0.000 claims description 2
- QELUAJBXJAWSRC-UHFFFAOYSA-N 4-nitrooxybutyl nitrate Chemical compound [O-][N+](=O)OCCCCO[N+]([O-])=O QELUAJBXJAWSRC-UHFFFAOYSA-N 0.000 claims description 2
- MIYIEPHJPVBSEV-UHFFFAOYSA-N 5-nitrooxypentyl nitrate Chemical compound [O-][N+](=O)OCCCCCO[N+]([O-])=O MIYIEPHJPVBSEV-UHFFFAOYSA-N 0.000 claims description 2
- 241000286209 Phasianidae Species 0.000 claims description 2
- 241000282849 Ruminantia Species 0.000 claims description 2
- RHVYBZNTBGYKKV-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] nitrate Chemical compound OCC(CO)(CO)CO[N+]([O-])=O RHVYBZNTBGYKKV-UHFFFAOYSA-N 0.000 claims description 2
- HSNWZBCBUUSSQD-UHFFFAOYSA-N amyl nitrate Chemical compound CCCCCO[N+]([O-])=O HSNWZBCBUUSSQD-UHFFFAOYSA-N 0.000 claims description 2
- 239000010828 animal waste Substances 0.000 claims description 2
- WOIVNLSVAKYSKX-UHFFFAOYSA-N benzyl nitrate Chemical compound [O-][N+](=O)OCC1=CC=CC=C1 WOIVNLSVAKYSKX-UHFFFAOYSA-N 0.000 claims description 2
- 235000013330 chicken meat Nutrition 0.000 claims description 2
- LYAGTVMJGHTIDH-UHFFFAOYSA-N diethylene glycol dinitrate Chemical compound [O-][N+](=O)OCCOCCO[N+]([O-])=O LYAGTVMJGHTIDH-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- LBHIOVVIQHSOQN-UHFFFAOYSA-N nicorandil Chemical compound [O-][N+](=O)OCCNC(=O)C1=CC=CN=C1 LBHIOVVIQHSOQN-UHFFFAOYSA-N 0.000 claims description 2
- 244000144977 poultry Species 0.000 claims description 2
- 235000013594 poultry meat Nutrition 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000002085 persistent effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910004679 ONO2 Inorganic materials 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000012872 agrochemical composition Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000009406 nutrient management Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000003911 water pollution Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05F—ORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C, e.g. FERTILISERS FROM WASTE OR REFUSE
- C05F3/00—Fertilisers from human or animal excrements, e.g. manure
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01C—PLANTING; SOWING; FERTILISING
- A01C3/00—Treating manure; Manuring
Definitions
- the present invention relates to a method to reduce emissions of methane originating from the manure management of livestock production. More particularly, it relates to the use of a nitrooxy organic compound to reduce methane emission from livestock manure.
- Methane is the most abundant organic chemical in the earth’s atmosphere, and its abundance is increasing with time and has reached levels not seen in recent geological history. Methane is produced both naturally and anthropogenically. One of the sources of anthropogenic methane is manure from domesticated animal.
- Nitrooxy organic molecules are very efficient in reducing methane emissions from manure originating from livestock production.
- Nitrooxy organic molecules as described below are very efficient in reducing methane emissions from manure management systems, they provide a persistent methane reduction, and are safe for the environment as well as for human.
- Manure management system means any way/system of managing the manure originating from livestock production. It refers to capture, storage, treatment, and utilization of animal manures in an environmentally sustainable manner. It can be retained in various holding facilities (for example swine pits). Animal manure (also referred to as animal waste) can occur in a liquid, slurry, or solid form. It is utilized by distribution on fields in amounts that enrich soils without causing water pollution or unacceptably high levels of nutrient enrichment. Manure management is a component of nutrient management.
- the term “animal” in connection with the present invention refers to any farm animal.
- farm animals are ruminants and monogastric animals, including but not limited to pigs or swine (including, but not limited to, piglets, growing pigs, and sows); poultry such as turkeys, and chicken (including but not limited to broiler chickens, chicks, layer hens.
- the problem to be solved by the present invention is to provide a method to reduce methane emissions from the manure generated by livestock production systems.
- the present inventors now surprisingly found that the compounds specified herein after, have a great potential for use in livestock manure management in order to reduce the formation of methane without affecting the environment. Said compounds are also more stable than those described in the prior art, safer for the environment and human using it, lead to persistent methane reduction effect, they do not affect the overall manure management systems, they can be produced at industrial scale at a cost compatible with the agrochemical industry, and they are active at very low concentration.
- the present invention provides the use of at least one organic molecule substituted at any position with at least one nitrooxy group, or a salt thereof as defined by formula (I) as an active compound for reducing the formation of methane emanating from livestock manure management systems.
- the invention further provides a method for reducing the production of methane emanating from the livestock manure management systems, comprising applying a sufficient amount of at least one organic molecule substituted at any position with at least one nitrooxy group, or a salt thereof as defined by formula (I) to the manure management system.
- organic molecules substituted at any position with at least one nitrooxy group, or salts thereof are defined by the following compound of formula (I)
- Y is an organic molecule of the following composition: C a HbOdN e S g , wherein a is comprised between 1 and 25, preferably between 1 and 10 b is comprised between 2 and 51 , preferably between 2 and 21 d is comprised between 0 and 8, preferably between 0 and 6 e is comprised between 0 and 5, preferably between 0 and 3 g is comprised between 0 and 3, preferably between 0 and 1.
- preferred compounds of formula (I) according to the present invention are compounds, wherein a is comprised between 1 and 10, preferably, a is comprised between 3 and 8.
- preferred compounds of formula (I) are compounds of formula (II), formula (II), wherein n is comprised between 0 and 12, preferably comprised between 0 and 6 and, wherein, if n 0, the carbon chain is a linear, a cyclic, or branched aliphatic carbon chain which may be non-substituted or substituted with up to 3 hydroxyl-, alkoxy-, amino-, alkylamino-, dialkylamino- or nitrooxy groups, or an alkenyl, or an alkynyl carbon chain mono- or polyunsaturated and in any isomeric form,
- R4 is independently, hydrogen or a saturated straight, cyclic or branched chain of an alkyl or alkenyl group containing 1 to 12, preferably 1 to 6 carbon atoms,
- X is hydrogen, R5, R5 N, -OR5, -OCOR5, -NR5R6, -ONO2, -COOR5, - CONR5R6, -NHSO2R5, or -SO2NHR5,
- R5 and R6 are independently, hydrogen, C1 -C12 straight, branched or cyclic alkyl chain, non substituted or substituted with up to 3 hydroxyl-, alkoxy-, amino-, alkylamino-, dialkylamino- or nitrooxy groups, alkenyl, or alkynyl carbon chain which may be mono or polyunsaturated, and in any isomeric form.
- the carbon chain when n > 2, can be linear or branched at any position along the carbon chain. In addition, the carbon chain can be branched by multiple branches at different positions along the carbon chain. Moreover, when n > 3, the aliphatic carbon chain may form a cyclic moiety. This cyclic moiety can carry the nitrooxy moiety at any position (2, 3, 4), and it can also be branched at multiple positions by any aliphatic groups. The branched aliphatic groups are preferably, methyl, ethyl or propyl. Moreover, the carbon chain may be further substituted with up to 3 hydroxyl- , alkoxy-, amino-, alkylamino-, dialkylamino- or nitrooxy groups.
- a preferred alkyl group is methyl, ethyl, propyl, isopropyl, butyl, sec. butyl, isobutyl, pentyl, neopentyl, hexyl, cyclohexyl, and 2-ethyl-hexyl and octyl.
- any alkyl or alkenyl group containing three or more carbon atoms can be straight chain, branched, or cyclic.
- more preferred compounds of formula (I) according to the present invention are selected from the list of compounds, and salts thereof comprising: 3-Nitrooxypropanol, racemate-4-Phenylbutane-1 ,2-diyl dinitrate, 2- (Hydroxymethyl)-2-(nitrooxymethyl)-1 ,3-propanediol, N-Ethyl-3-nitrooxy-propionic sulfonyl amide, 5-Nitrooxy-pentanenitrile, 5-Nitrooxy-pentane, 3-Nitrooxy-propyl propionate, 1 ,3-bis-Nitrooxypropane, 1 ,4-bis-Nitrooxybutane, 1 ,5-bis- Nitrooxypentane, 3-Nitrooxy-propyl benzoate, 3-Nitrooxy-propyl hexanoate, 3- Nitrooxy-propyl 5-nitrooxy-hexanoate, Benz
- the nitrooxy organic molecule is preferably applied as an agrochemical composition further comprising an agrochemical adjuvant.
- a preferred nitrooxy organic compound is 3 Nitrooxypropanol (CAS-No: 100502-66-7). It is a known compound which can e.g. be manufactured as outlined in WO-2004043898 or WO-2012084629. Suitable formulations thereof are e.g. disclosed in WO-2018149755, WO-2018149756, WO-2018091643 or WO- 2019007740.
- the nitrooxyorgan ic compound can be administered once or in regular intervals to the slurry or manure of the farm animals. More preferably, the administration of the nitrooxyorgan ic compound is such that it reaches a concentration of between 10 and 2000 mg nitrooxy organic compound / kg animal manure or slurry.
- Methane concentration can be measured from manure by standard methods.
- Swine pit has been treated with 3 Nitrooxypropanol formulated as described in WO-2018149755.
- the nitrooxy organic compound has been administered such that it reaches a concentration of 500, 1000 and 2000 mg nitrooxy organic compound / kg animal slurry.
- Methane concentration in the slurry i.e. methane production of the slurry, has been measured over a period of about 120 hours and compered with untreated slurry.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The present invention relates to a method to reduce emissions of methane originating from the manure management of livestock production. More particularly, it relates to the use of a nitrooxy organic compound to reduce methane emission from livestock manure, in particular from swine manure slurry.
Description
NEW METHOD FOR SUSTAINABLE MANURE MANAGEMENT
Technical Field
The present invention relates to a method to reduce emissions of methane originating from the manure management of livestock production. More particularly, it relates to the use of a nitrooxy organic compound to reduce methane emission from livestock manure.
Background of the invention
Methane is the most abundant organic chemical in the earth’s atmosphere, and its abundance is increasing with time and has reached levels not seen in recent geological history. Methane is produced both naturally and anthropogenically. One of the sources of anthropogenic methane is manure from domesticated animal.
Thus, in view of the greenhouse gas global warming challenge, there is an urgent need to find new solutions to significantly reduce methane emissions from the manure generated by livestock production. The present inventors surprisingly found that Nitrooxy organic molecules are very efficient in reducing methane emissions from manure originating from livestock production. Thus Nitrooxy organic molecules as described below are very efficient in reducing methane emissions from manure management systems, they provide a persistent methane reduction, and are safe for the environment as well as for human.
“Manure management system” means any way/system of managing the manure originating from livestock production. It refers to capture, storage, treatment, and utilization of animal manures in an environmentally sustainable manner. It can be retained in various holding facilities (for example swine pits). Animal manure (also referred to as animal waste) can occur in a liquid, slurry, or solid form. It is utilized by distribution on fields in amounts that enrich soils without causing water pollution or unacceptably high levels of nutrient enrichment. Manure management is a component of nutrient management.
The term “animal” in connection with the present invention refers to any farm animal. Examples of farm animals are ruminants and monogastric animals, including but not limited to pigs or swine (including, but not limited to, piglets, growing pigs, and sows); poultry such as turkeys, and chicken (including but not limited to broiler chickens, chicks, layer hens.
Summary of the invention
Therefore, the problem to be solved by the present invention is to provide a method to reduce methane emissions from the manure generated by livestock production systems.
Further aspects of the invention are subject of further independent claims. Particularly preferred embodiments are subject of dependent claims.
Detailed description of the invention
The present inventors now surprisingly found that the compounds specified herein after, have a great potential for use in livestock manure management in order to reduce the formation of methane without affecting the environment. Said compounds are also more stable than those described in the prior art, safer for the environment and human using it, lead to persistent methane reduction effect, they do not affect the overall manure management systems, they can be produced at industrial scale at a cost compatible with the agrochemical industry, and they are active at very low concentration.
Therefore, the present invention provides the use of at least one organic molecule substituted at any position with at least one nitrooxy group, or a salt thereof as defined by formula (I) as an active compound for reducing the formation of methane emanating from livestock manure management systems.
The invention further provides a method for reducing the production of methane emanating from the livestock manure management systems, comprising
applying a sufficient amount of at least one organic molecule substituted at any position with at least one nitrooxy group, or a salt thereof as defined by formula (I) to the manure management system.
In all embodiments of the present invention, organic molecules substituted at any position with at least one nitrooxy group, or salts thereof are defined by the following compound of formula (I)
O2N._Y u formula (I) wherein Y is an organic molecule of the following composition: CaHbOdNeSg, wherein a is comprised between 1 and 25, preferably between 1 and 10 b is comprised between 2 and 51 , preferably between 2 and 21 d is comprised between 0 and 8, preferably between 0 and 6 e is comprised between 0 and 5, preferably between 0 and 3 g is comprised between 0 and 3, preferably between 0 and 1.
In another embodiment, preferred compounds of formula (I) according to the present invention are compounds, wherein a is comprised between 1 and 10, preferably, a is comprised between 3 and 8.
In another embodiment, preferred compounds of formula (I) according to the present invention are compounds of formula (II),
formula (II), wherein n is comprised between 0 and 12, preferably comprised between 0 and 6 and, wherein, if n 0, the carbon chain is a linear, a cyclic, or branched aliphatic carbon chain which may be non-substituted or substituted with up to 3 hydroxyl-, alkoxy-, amino-, alkylamino-, dialkylamino- or nitrooxy groups, or an alkenyl, or an alkynyl carbon chain mono- or polyunsaturated and in any isomeric form,
R4 is independently, hydrogen or a saturated straight, cyclic or branched chain of an alkyl or alkenyl group containing 1 to 12, preferably 1 to 6 carbon atoms,
X is hydrogen, R5, R5 N, -OR5, -OCOR5, -NR5R6, -ONO2, -COOR5, - CONR5R6, -NHSO2R5, or -SO2NHR5,
R5 and R6 are independently, hydrogen, C1 -C12 straight, branched or cyclic alkyl chain, non substituted or substituted with up to 3 hydroxyl-, alkoxy-, amino-, alkylamino-, dialkylamino- or nitrooxy groups, alkenyl, or alkynyl carbon chain which may be mono or polyunsaturated, and in any isomeric form.
For all embodiments of the present invention, it is to be understood that compounds of formula (I) and compounds of formula (II) can be in any isomeric form.
It is to be understood in the above definition of compounds of formula (II) that when n > 2, the carbon chain can be linear or branched at any position along the carbon chain. In addition, the carbon chain can be branched by multiple branches at different positions along the carbon chain. Moreover, when n > 3, the aliphatic
carbon chain may form a cyclic moiety. This cyclic moiety can carry the nitrooxy moiety at any position (2, 3, 4), and it can also be branched at multiple positions by any aliphatic groups. The branched aliphatic groups are preferably, methyl, ethyl or propyl. Moreover, the carbon chain may be further substituted with up to 3 hydroxyl- , alkoxy-, amino-, alkylamino-, dialkylamino- or nitrooxy groups.
In the above definition of derivatives of the formula (II) a preferred alkyl group is methyl, ethyl, propyl, isopropyl, butyl, sec. butyl, isobutyl, pentyl, neopentyl, hexyl, cyclohexyl, and 2-ethyl-hexyl and octyl. Furthermore any alkyl or alkenyl group containing three or more carbon atoms can be straight chain, branched, or cyclic. In addition for the straight chain or branched C2-C -alkenylene group, this is understood to encompass alkenylene groups with one or (from C4) more double bonds; examples of such alkenylene groups are those of the formulae -CH=CH-, - CH=CH-CH2-, -CH=CH-(CH2)3- and -(CH=CH)2-.
In another embodiment, more preferred compounds of formula (I) according to the present invention are selected from the list of compounds, and salts thereof comprising: 3-Nitrooxypropanol, racemate-4-Phenylbutane-1 ,2-diyl dinitrate, 2- (Hydroxymethyl)-2-(nitrooxymethyl)-1 ,3-propanediol, N-Ethyl-3-nitrooxy-propionic sulfonyl amide, 5-Nitrooxy-pentanenitrile, 5-Nitrooxy-pentane, 3-Nitrooxy-propyl propionate, 1 ,3-bis-Nitrooxypropane, 1 ,4-bis-Nitrooxybutane, 1 ,5-bis- Nitrooxypentane, 3-Nitrooxy-propyl benzoate, 3-Nitrooxy-propyl hexanoate, 3- Nitrooxy-propyl 5-nitrooxy-hexanoate, Benzylnitrate, isosorbid-dinitrate, and N-[2- (Nitrooxy)ethyl]-3-pyridinecarboxamide, 2-Nitro-5-nitrooxymethyl-furan, and Bis-(2- nitrooxyethyl) ether as listed in Table 1 :
Table 1 : Preferred compounds of formula (I) according to the present invention
The nitrooxy organic molecule is preferably applied as an agrochemical composition further comprising an agrochemical adjuvant.
A preferred nitrooxy organic compound is 3 Nitrooxypropanol (CAS-No: 100502-66-7). It is a known compound which can e.g. be manufactured as outlined in WO-2004043898 or WO-2012084629. Suitable formulations thereof are e.g. disclosed in WO-2018149755, WO-2018149756, WO-2018091643 or WO- 2019007740.
The nitrooxyorgan ic compound can be administered once or in regular intervals to the slurry or manure of the farm animals. More preferably, the administration of the nitrooxyorgan ic compound is such that it reaches a concentration of between 10 and 2000 mg nitrooxy organic compound / kg animal manure or slurry.
Methane concentration can be measured from manure by standard methods.
Example
Treatment of slurry in Swin pit with 3 Nitrooxypropanol
Swine pit has been treated with 3 Nitrooxypropanol formulated as described in WO-2018149755. In three parallel test series, the nitrooxy organic compound has been administered such that it reaches a concentration of 500, 1000 and 2000 mg nitrooxy organic compound / kg animal slurry.
Methane concentration in the slurry, i.e. methane production of the slurry, has been measured over a period of about 120 hours and compered with untreated slurry.
The results (Figure 1 ) show a clear response that the treatment of animal manure with a nitrooxy organic compound according to the invention decreases methane product and thus provides a significant reduction of methane emissions from manure management systems (swine pit).
Claims
1 . Method for reducing the production of methane emanating from livestock manure management systems, comprising applying a sufficient amount of at least one organic molecule substituted at any position with at least one nitrooxy group, or a salt thereof as defined by formula (I) to the manure management system,
formula (I), wherein Y is an organic molecule of the following composition: CaHbOdNeSg, wherein a is comprised between 1 and 25, b is comprised between 2 and 51 , d is comprised between 0 and 8, e is comprised between 0 and 5, g is comprised between 0 and 3.
2. Method according to claim 1 wherein the at least one organic molecule substituted at any position with at least one nitrooxy group is selected from: 3-Nitrooxypropanol, racemate-4-Phenylbutane-1 ,2-diyl dinitrate, 2- (Hydroxymethyl)-2-(nitrooxymethyl)-1 ,3-propanediol, N-Ethyl-3-nitrooxy- propionic sulfonyl amide, 5-Nitrooxy-pentanenitrile, 5-Nitrooxy-pentane, 3- Nitrooxy-propyl propionate, 1 ,3-bis-Nitrooxypropane, 1 ,4-bis- Nitrooxybutane, 1 ,5-bis-Nitrooxypentane, 3-Nitrooxy-propyl benzoate, 3- Nitrooxy-propyl hexanoate, 3-Nitrooxy-propyl 5-nitrooxy-hexanoate, Benzylnitrate, isosorbid-dinitrate, and N-[2-(Nitrooxy)ethyl]-3- pyridinecarboxamide, 2-Nitro-5-nitrooxymethyl-furan, and Bis-(2- nitrooxyethyl) ether.
Method according to claim 1 wherein the at least one organic molecule substituted at any position with at least one nitrooxy group is selected from: 3- Nitrooxypropanol. Method according to any of claims 1 to 3, wherein manure management system means any way/system of managing the manure originating from livestock production, it refers to capture, storage, treatment, and utilization of animal manures in an environmentally sustainable manner and wherein animal manure (also referred to as animal waste) can occur in a liquid, slurry, or solid form. Method according to any of claims 1 to 4, wherein the term animal refers to any farm animal, examples of farm animals are ruminants and monogastric animals, including but not limited to pigs or swine (including, but not limited to, piglets, growing pigs, and sows); poultry such as turkeys, and chicken (including but not limited to broiler chickens, chicks, layer hens.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP22213514 | 2022-12-14 | ||
| EP22213514.7 | 2022-12-14 |
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| WO2024126430A1 true WO2024126430A1 (en) | 2024-06-20 |
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| Application Number | Title | Priority Date | Filing Date |
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| PCT/EP2023/085221 WO2024126430A1 (en) | 2022-12-14 | 2023-12-11 | New method for sustainable manure management |
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| WO (1) | WO2024126430A1 (en) |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004043898A1 (en) | 2002-11-14 | 2004-05-27 | Dipharma S.P.A. | A process for the mononitration of alkanediols |
| WO2012084629A1 (en) | 2010-12-20 | 2012-06-28 | Dsm Ip Assets B.V. | Use of nitrooxy organic molecules in feed for reducing methane emission in ruminants, and/or to improve ruminant performance |
| WO2018091643A1 (en) | 2016-11-18 | 2018-05-24 | Dsm Ip Assets B.V. | Powderous formulations |
| WO2018149755A1 (en) | 2017-02-14 | 2018-08-23 | Dsm Ip Assets B.V. | Water dispersible formulations |
| WO2018149756A1 (en) | 2017-02-14 | 2018-08-23 | Dsm Ip Assets B.V. | Storage-stable formulations |
| WO2019007740A1 (en) | 2017-07-07 | 2019-01-10 | Dsm Ip Assets B.V. | Compressed tablets |
| WO2022015950A1 (en) * | 2020-07-15 | 2022-01-20 | Locus Ip Company, Llc | Improved methods and compositions for processing manure |
| CN114632411A (en) * | 2022-03-30 | 2022-06-17 | 江苏省农业科学院 | Carbon nitrogen emission reduction method applied to urine, excrement and sewage in pig farm |
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2023
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|---|---|---|---|---|
| WO2004043898A1 (en) | 2002-11-14 | 2004-05-27 | Dipharma S.P.A. | A process for the mononitration of alkanediols |
| WO2012084629A1 (en) | 2010-12-20 | 2012-06-28 | Dsm Ip Assets B.V. | Use of nitrooxy organic molecules in feed for reducing methane emission in ruminants, and/or to improve ruminant performance |
| WO2018091643A1 (en) | 2016-11-18 | 2018-05-24 | Dsm Ip Assets B.V. | Powderous formulations |
| WO2018149755A1 (en) | 2017-02-14 | 2018-08-23 | Dsm Ip Assets B.V. | Water dispersible formulations |
| WO2018149756A1 (en) | 2017-02-14 | 2018-08-23 | Dsm Ip Assets B.V. | Storage-stable formulations |
| WO2019007740A1 (en) | 2017-07-07 | 2019-01-10 | Dsm Ip Assets B.V. | Compressed tablets |
| WO2022015950A1 (en) * | 2020-07-15 | 2022-01-20 | Locus Ip Company, Llc | Improved methods and compositions for processing manure |
| CN114632411A (en) * | 2022-03-30 | 2022-06-17 | 江苏省农业科学院 | Carbon nitrogen emission reduction method applied to urine, excrement and sewage in pig farm |
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| Title |
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| DATABASE WPI Week 2022006, Derwent World Patents Index; AN 2022-84470K, XP002809306 * |
| no. 100502-66-7 |
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