CN112004794A - 新颖的二羧酸二酯 - Google Patents
新颖的二羧酸二酯 Download PDFInfo
- Publication number
- CN112004794A CN112004794A CN201980027750.9A CN201980027750A CN112004794A CN 112004794 A CN112004794 A CN 112004794A CN 201980027750 A CN201980027750 A CN 201980027750A CN 112004794 A CN112004794 A CN 112004794A
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- CN
- China
- Prior art keywords
- dicarboxylic acid
- acid diester
- formula
- feed
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
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- -1 dicarboxylic acid diesters Chemical class 0.000 title claims abstract description 56
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 62
- 241000282849 Ruminantia Species 0.000 claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 241001465754 Metazoa Species 0.000 claims description 15
- 241000283690 Bos taurus Species 0.000 claims description 13
- 229940088594 vitamin Drugs 0.000 claims description 13
- 229930003231 vitamin Natural products 0.000 claims description 13
- 235000013343 vitamin Nutrition 0.000 claims description 13
- 239000011782 vitamin Substances 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003674 animal food additive Substances 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
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- 125000002947 alkylene group Chemical group 0.000 claims description 4
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- YNGRGHODNDCZCC-UHFFFAOYSA-N nitro hydrogen sulfate Chemical compound OS(=O)(=O)O[N+]([O-])=O YNGRGHODNDCZCC-UHFFFAOYSA-N 0.000 claims description 4
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- FVMCNNRIVRMXCR-UHFFFAOYSA-N bis(3-nitrooxypropyl) propanedioate Chemical compound C(CC(=O)OCCCO[N+](=O)[O-])(=O)OCCCO[N+](=O)[O-] FVMCNNRIVRMXCR-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- A23K20/105—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
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
-
- 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
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Abstract
本发明涉及新颖的二羧酸二酯及其用于抑制反刍动物中的甲烷产生的用途。
Description
本发明涉及新颖的二羧酸二酯以及其用于抑制反刍动物的甲烷产生的用途。
地球周围空气的温度正在升高,该过程被称为全球变暖。减少这种变暖效应的主要焦点之一是减少排放到大气中的温室气体的量。温室气体从几个不同的天然和人工来源排放;然而,最重点的两个来源是农业产业和化石燃料工业。在农业中,反刍动物,特别是牛,是生物甲烷形成的主要贡献者,并且据估计,阻止由反刍动物形成甲烷几乎会稳定大气中的甲烷浓度。
来自反刍动物畜牧业的甲烷排放—来自植物生物质在反刍动物消化系统中的肠道发酵的副产物—是由产甲烷古细菌(methanogenic archaea)产生的。在过去的十年中已经进行了各种尝试来减轻来自反刍动物的甲烷产生。尽管方法不同,但是迄今为止最流行的方法是饲料添加剂,所述饲料添加剂通过降低或抑制产甲烷古细菌的甲烷产生而在瘤胃液中起作用。然而,已经发现许多甲烷还原剂(例如3-硝基氧基丙醇)具有相对较高的蒸气压,所述相对较高的蒸气压使所述甲烷还原剂极度存储不稳定,即活性物质易在存储时损失。因此,通常必须过量投加甲烷抑制剂,这是不希望的。
因此,持续需要表现出有效的甲烷还原效应的甲烷抑制剂。此外,此类化合物应在20℃下表现出低蒸气压(即小于0.01mbar的蒸气压)以增强其存储稳定性。
令人惊讶地,现已发现某些新颖的二羧酸二酯能够有效地抑制瘤胃液中的甲烷形成,同时表现出非常低的蒸气压,这使得它们更存储稳定。
因此,在第一实施方式中,本发明涉及式(I)的二羧酸二酯。
其中
n是选自1至15的范围的整数,并且
X是C1-24亚烷基基团、C2-24亚烯基基团或C6-24亚芳基基团,前提条件是当n>3时,所得烃链可被-O-或-NH-中断,
在一个优选实施方式中,本发明涉及式(I)的二羧酸二酯,其中n是选自1至15的范围的整数,并且X是C1-24亚烷基基团、C2-24亚烯基基团或C6-24亚芳基基团。
术语C1-24亚烷基基团是指具有1至24个碳原子的直链C1-24亚烷基基团或3至24个碳原子的环状C3-24亚烷基基团,所述基团可以任选地在任何碳原子处被C1-C26烷基基团取代。所述C1-C26烷基取代基优选地选自由以下项组成的组:甲基、辛烯基、壬烯基、癸烯基、十一碳烯基或十二碳烯基。在本发明的所有实施方式中优选的C1-24亚烷基基团是直链的(未取代的)C1-24亚烷基基团(即*-(CH2)m-*),其中m是选自1至24的范围的整数;以及未取代的环状C3-6亚烷基基团,例如但不限于亚乙基、亚乙基、亚丙基、亚丁基、亚戊基、亚己基、1,2-亚环戊基、1,2-亚环己基和1,4-亚环己基。在本发明的所有实施方式中特别优选的C1-24亚烷基基团是直链的(未取代的)C1-10亚烷基基团,甚至更优选的是直链(未取代的)C1-5亚烷基基团,例如特别是亚甲基、亚乙基和亚丙基。
如本文所用的术语C2-24亚烯基基团是指具有2至24个碳原子的直链C2-24烷基基团或3至24个碳原子的环状C3-24烷基基团,所述基团具有至少一个碳-碳双键,可以彼此独立地为(E)或(Z)构型,并且可以任选地在任何碳原子处被如上所定义的烷基基团(例如但不限于伸乙烯基(vinylene)(亚乙烯基)、亚丙烯基、亚丁烯基和亚环己烯基)取代。在本发明的所有实施方式中优选的C2-24亚烯基基团是直链的C2-24-亚烯基基团,即*-(CH2)o-(CH=CH)p-(CH2)q-*双自由基,其中o是选自0至22的范围的整数,p是选自1至12的范围的整数,并且q是选自0至22的范围的整数。在本发明的所有实施方式中特别优选的C2-24亚烯基基团是伸乙烯基((E)或(Z)构型)。
术语C6-24亚芳基基团是指可任选地在任何碳原子处被如上所定义的烷基基团取代的芳族芳基双自由基。优选地,在本发明的所有实施方式中,C6-24亚芳基基团未被取代或被一个甲基基团取代。在本发明的所有实施方式中特别优选的是C6-10亚芳基基团,例如特别是1,2-亚苯基、1,3-亚苯基、1,4-亚苯基、(甲基)-1,2-亚苯基和2,6-亚萘基。
在本发明的所有实施方式中,n优选地选自3至9的范围,更优选地选自3至6的范围。最优选地,在本发明的所有实施方式中,n是3。
在本发明的所有实施方式中,X优选地选自由C1-10亚烷基基团、C2-5亚烯基基团和C6-10亚芳基基团组成的组,更优选地选自由未取代的C1-10亚烷基基团、未取代的C2-5亚烯基基团和未取代的C6-10亚芳基基团组成的组,最优选地选自由未取代的C1-5亚烷基基团、未取代的C2-4亚烯基基团、1,2-亚苯基、1,3-亚苯基和1,4-亚苯基组成的组,例如特别是选自由未取代的C1-3亚烷基基团和伸乙烯基(即*-(CH=CH)-*))组成的组。此外优选的是如果所述亚烷基或亚烯基基团是直链亚烷基或亚烯基基团。
表1中列出了特别有利的式(I)的二羧酸二酯。
表1
可以根据本领域中已知用于制备硝基氧基有机分子以及酯的标准方法来制造本发明的化合物。硝基氧基团可以例如在相应的醇与硝基硫酸的反应中引入。二酯可以例如通过将相应的二羧酸或其对应的酰氯或(环状)酸酐用硝基氧基链烷醇或二醇进行酯化来制备。
因此,本发明还涉及一种用于制造式(I)的二酯的方法,所述方法包括使式(II)的二羧酸或其酰氯或(环状)酸酐与式(III)的硝基氧基醇反应的步骤。
另选地,在第一步骤中,可以使脂肪酸与相应的二醇反应以形成单酯,之后使所述相应的单酯与硝基硫酸反应。
因此,在另一个实施方式中,本发明涉及一种用于制备式(I)的二羧酸二酯的方法,所述方法包括使式(II)的脂肪酸或其酰氯或(环状)酸酐与式(IV)的醇反应的步骤,之后使获得的脂肪酸单酯(V)与硝基硫酸反应成式(I)的二酯。
众所周知的是,如本文所给出的所有定义和优选项也适用于根据本发明的方法。
合适的二羧酸的示例包括直链饱和二羧酸,例如特别是丙二酸、琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸和癸二酸;不饱和二羧酸,例如特别是马来酸、富马酸、戊烯二酸和中康酸;环状饱和二羧酸,例如1,2-环戊烷二羧酸、1,2-二环己烷二羧酸;以及环状不饱和二羧酸,例如反式-4-环己烯-1,2-二羧酸;以及芳族二羧酸,例如特别是邻苯二甲酸、间苯二甲酸、对苯二甲酸和2,6-萘二羧酸。
合适的环状酸酐的示例包括邻苯二甲酸酐、四氢邻苯二甲酸酐、萘二羧酸酐、六氢邻苯二甲酸酐、5-降冰片烯-2,3-二羧酸酐、降冰片烯-2,3-二羧酸酐、萘二羧酸酐、2-十二碳烯-1-基-琥珀酸酐、马来酸酐、偏苯三酸酐、(甲基、辛基或十二碳烯基)琥珀酸酐、戊二酸酐、4-甲基邻苯二甲酸酐、4-甲基六氢邻苯二甲酸酐和4-甲基四氢邻苯二甲酸酐。
在根据本发明的方法中优选的二羧酸选自由丙二酸、马来酸、富马酸、琥珀酸和戊二酸组成的组,最优选地选自由丙二酸、琥珀酸和富马酸组成的组。
在根据本发明的方法中,最优选的式(III)的醇或式(IV)的二醇是3-硝基氧基丙醇或1,3-丙二醇。
在另一个实施方式中,本发明涉及至少一种如由式(I)定义并且具有如本文所给出的所有定义和优选项的二羧酸二酯作为动物饲料中的活性化合物以减少源自反刍动物的消化活动的甲烷形成和/或改善反刍动物性能的用途。
本发明还提供了一种用于减少源自反刍动物的消化活动的甲烷产生和/或改善反刍动物的动物性能的方法,所述方法包括向所述动物口服施用足量的至少一种如由式(I)所定义并且具有如本文所给出的所有定义和优选项的二羧酸二酯。应当理解的是口服施用是指简单地喂食或手动施用大丸药(bolus)。
根据本发明的二羧酸二酯特别适合用于在延长的时间段内起作用,即在施用之后至少10小时,优选地至少16小时,最优选地至少20小时的时段内,例如在施用之后24小时的时间段内起作用。
因此,本发明还涉及根据本发明的用途或方法,其中各剂量在时间上彼此分开至少10小时,优选地至少16小时、更优选地至少20小时、最优选地至少24小时。
根据本发明的反刍哺乳动物包括牛、山羊、绵羊、长颈鹿、美洲野牛、欧洲野牛、牦牛、水牛、鹿、骆驼、羊驼、美洲驼、角马、羚羊、叉角羚和蓝牛羚。
对于本发明的所有实施方式,家牛、绵羊和山羊是更优选的物种。对于本发明的目的,最优选的物种是家牛。该术语包括家牛的所有种族,以及所有生产种类的牛,特别是奶牛和肉牛。
本发明还涉及至少一种如由式(I)定义并且具有如本文所给出的所有定义和优选项的二羧酸二酯的用途,其中当在代谢室中测量时,以升/千克干物质摄入量计算的反刍动物甲烷产生减少了至少10%。优选地,甲烷减少了至少15%,更优选地至少20%,甚至更优选地至少25%,最优选地至少30%。也可以使用替代的甲烷排放测量,如使用激光束或对于奶牛反刍动物,将甲烷产生与牛奶中的挥发性脂肪酸(VFA)组成相关联。
本发明还涉及至少一种如由式(I)定义并且具有如本文所给出的所有定义和优选项的二羧酸二酯的用途,其中向反刍动物施用的所述至少一种二羧酸二酯的量选自1mg/kg饲料至10g/kg饲料,优选地10mg/kg饲料至1g/kg饲料,更优选地50mg/kg饲料至500mg/kg饲料的范围。
如上所述,本发明的二羧酸二酯可用作用于反刍动物的饲料添加剂和动物饲料组合物的化合物,并且因此可用作此类饲料中的活性成分以减少所述动物的消化道中的甲烷形成和/或改善反刍动物性能。
为了实现它们作为反刍动物饲料的此类成分的用途,可以通过在饲料配制和加工领域中本身已知的方法将至少一种如由式(I)定义并且具有如本文所给出的所有定义和优选项的二羧酸二酯掺入饲料中。
因此,本发明的另外方面是制剂,即饲料添加剂和动物饲料组合物,所述制剂含有至少一种如由式(I)定义并且具有如本文所给出的所有定义和优选项的二羧酸二酯。
因此,本发明还涉及一种饲料组合物或饲料添加剂,所述饲料组合物或饲料添加剂包含至少一种如由式(I)定义并且具有如本文所给出的所有定义和优选项的二羧酸二酯。优选地,饲料组合物或饲料添加剂是反刍动物基料混合物。在优选的实施方式中,组合物是矿物质预混物、包含维生素和矿物质的维生素预混物、或大丸药。
通过饲料摄入提供给动物的根据本发明的二羧酸二酯的正常日剂量取决于动物的种类及其状况。通常该剂量应在约1mg化合物/kg饲料至约10g化合物/kg饲料,优选地约10mg化合物/kg饲料至约1g化合物/kg饲料,更优选地50mg化合物/kg饲料至500mg化合物/kg饲料的范围内。
所述至少一种如由式(I)定义并且具有如本文所给出的所有定义和优选项的二羧酸二酯可以与动物饲料组合物(饮食)中存在的常规成分(例如碳酸钙,电解质例如氯化铵,蛋白质例如豆粕粉、小麦、淀粉、葵籽饼粉、玉米、肉和骨粉,氨基酸,动物脂肪,维生素和微量矿物质)组合使用。
本发明的组合物的具体示例如下:
-动物饲料添加剂,所述动物饲料添加剂包含(a)至少一种选自表1的化合物,和(b)至少一种脂溶性维生素,(c)至少一种水溶性维生素,(d)至少一种微量矿物质,和/或(e)至少一种巨量矿物质;
-动物饲料组合物,所述动物饲料组合物包含至少一种选自表1的化合物和50g/kg饲料至800g/kg饲料的粗蛋白含量。
因此,在一个优选的实施方式中,本发明涉及一种反刍动物饲料组合物或饲料添加剂。
所谓的预混物是本发明的动物饲料添加剂的示例。预混物表示一种或多种微量成分与稀释剂和/或载体的优选均匀的混合物。预混物用于促进微量成分在较大混合物中的均匀分散。
除了本发明的二羧酸二酯之外,本发明的预混物优选地还含有至少一种脂溶性维生素和/或至少一种水溶性维生素和/或至少一种微量矿物质和/或至少一种巨量矿物质。换句话说,本发明的预混物包含根据本发明的至少一种化合物以及至少一种选自由脂溶性维生素、水溶性维生素、微量矿物质和巨量矿物质组成的组的附加组分。
可以将巨量矿物质单独添加到饲料中。因此,在一个特定实施方式中,预混物包含本发明的二羧酸二酯以及至少一种选自由脂溶性维生素、水溶性维生素和微量矿物质组成的组的附加组分。
以下是这些组分的示例的非排他性列表:
-脂溶性维生素的示例包括维生素A、维生素D3、维生素E和维生素K(例如维生素K3)。
-水溶性维生素的示例是维生素B12、生物素和胆碱、维生素B1、维生素B2、维生素B6、烟酸、叶酸和泛酸盐,例如D-泛酸钙。
-微量矿物质的示例是锰、锌、铁、铜、碘、硒和钴。
-巨量矿物质的示例是钙、磷和钠。
关于用于诸如牛等反刍动物的饲料组合物及其成分,反刍动物饮食通常由易于降解的部分(称为精饲料)和富含纤维的较不易降解的部分(称为干草、草料或粗饲料)组成。
干草由晒干的草、豆类或全谷物制成。所述草尤其包括梯牧草、黑麦草、羊茅草。豆类尤其包括三叶草、紫花苜蓿或苜蓿、豌豆、菜豆(bean)和巢菜(vetch)。全谷物尤其包括大麦、玉蜀黍(玉米)、燕麦、高粱。其他草料作物包括甘蔗、羽衣甘蓝、油菜和卷心菜。还使用块根作物来饲喂反刍动物,诸如萝卜、蕉青甘蓝、饲料甜菜(mangel)、饲用甜菜(fodder beet)和糖用甜菜(包括甜菜粕和甜菜糖蜜)。另外的作物是块茎类,诸如马铃薯、木薯和甘薯。青贮饲料是富含纤维的部分的青贮形式(例如,来自草、豆类或全谷物),其中将具有高水含量的材料用受控的厌氧发酵过程进行处理(天然发酵或用添加剂处理)。
精饲料主要由谷类(诸如大麦(包括啤酒粕和蒸馏酒粕)、玉蜀黍、小麦、高粱)组成,但通常也包含富含蛋白质的饲料成分,诸如大豆、油菜籽、棕榈仁、棉籽和向日葵。
牛也可以饲喂全混合日粮(TMR),其中在饲喂前将所有饮食组分(例如草料、青贮饲料和精饲料)混合。
如上所述,预混料是饲料添加剂的示例,所述预混料可以包含至少一种如由式(I)定义并且具有如本文所给出的所有定义和优选项的二羧酸二酯。应当理解的是,根据本发明的二羧酸二酯可以以不同的其他形式施用于动物。例如,二羧酸二酯还可以包含在大丸药中,所述大丸药将放置在瘤胃中并且将在特定的时间段内以明确剂量连续释放限定量的二羧酸二酯。
本发明还涉及一种用于减少源自反刍动物的消化活动的甲烷产生和/或用于改善反刍动物动物性能的方法,所述方法包括口服施用足量的至少一种如由式(I)定义并且具有如本文所给出的所有定义和优选项的二羧酸二酯。
此外,本发明还涉及如上所述的方法,其中向所述动物施用式(I)的二羧酸二酯与至少一种选自由二烯丙基二硫化物、大蒜油、异硫氰酸烯丙酯、脱氧胆酸、鹅脱氧胆酸以及它们的衍生物组成的组的附加活性物质的组合。
本发明还涉及如上所述的方法,其中所述反刍动物选自由牛、山羊、绵羊、长颈鹿、美洲野牛、欧洲野牛、牦牛、水牛、鹿、骆驼、羊驼、美洲驼、角马、羚羊、叉角羚和蓝牛羚组成的组,更优选地选自由牛、山羊和绵羊组成的组。
本发明还涉及如上所述的方法,其中施用于反刍动物的所述至少一种如由式(I)定义并且具有如本文所给出的所有定义和优选项的二羧酸二酯的量为约1mg化合物/kg饲料至约10g化合物/kg饲料,优选地约10mg化合物/kg饲料至约1g化合物/kg饲料,更优选地50mg化合物/kg饲料至500mg化合物/kg饲料。
本发明还涉及如上所述的方法,其中当在代谢室中测量时,以升/千克干物质摄入量计算的反刍动物甲烷产生减少了至少10%。优选地,甲烷减少至少15%,更优选地至少20%,甚至更优选地至少25%,最优选地至少30%。也可以使用替代的甲烷排放测量,如使用激光束或对于奶牛反刍动物,将甲烷产生与牛奶中的VFA组成相关联。
本发明还涉及如上所述的方法,其中当在常规性能试验中测量时,所述反刍动物饲料转化率降低了至少1%。优选地,饲料转化率降低了至少2%,更优选地至少2.5%,甚至更优选地至少3%,最优选地至少3.5%。
通过以下实施例进一步描述本发明,这些实施例不应解释为限制本发明的范围。
实施例1:3-硝基氧基-丙基二酯的合成
a.)丙二酸双(3-(硝基氧基)丙基)酯(I-a)的制备
将12.7g的3-硝基氧基丙醇、60ml的二氯甲烷和6.2ml的三乙胺放入三颈圆底烧瓶中,并将澄清溶液冷却至0℃。将7.3g的丙二酰氯溶于10ml二氯甲烷中,转移到滴液漏斗中,并在15分钟内滴加到3-硝基氧基丙醇溶液中,观察到有气体形成。将温度升至28℃。在完成添加后,将混合物在室温下搅拌20小时。然后加入5g无水碳酸钾(CO2形成),并将橙色悬浮液搅拌30分钟。滤出固体,并用20mL二氯甲烷洗涤。将澄清的橙色滤液在减压(10mbar,40℃浴温)下浓缩。获得了为橙色油状物的15.6g产物。将粗产物通过在50ml甲基叔丁基醚(MTBE)中稀释而纯化,并用50ml水洗涤十次,经硫酸钠干燥并减压浓缩。获得了14.2g纯产物(纯度:93%;蒸气压:0.00133mbar)。
b.)富马酸双(3-(硝基氧基)丙基)酯(I-b)的制备
将4.89g的3-硝基氧基丙醇、24.3ml的二氯甲烷和6.2ml的三乙胺放入三颈圆底烧瓶中,并将澄清溶液冷却至0℃。将富马酰氯(2.28ml)溶于10ml二氯甲烷中,转移到滴液漏斗中,并在15分钟内滴加到3-硝基氧基丙醇溶液中,保持温度低于5℃。颜色立即变为深棕色。最后,将混合物加温至24℃,并保持搅拌4小时。然后将粘性反应混合物用200ml乙酸乙酯稀释,并用200ml 2N盐酸萃取。然后将水相用100ml乙酸乙酯再萃取,并将合并的有机相用每次200mL的水洗涤三次(总共600mL)。将有机相经硫酸钠干燥,并在减压下(40℃/<0.1mbar)浓缩。获得了为深棕色油状物的5.2g产物。将粗产物通过柱色谱法(120g SiO2柱,洗脱剂为含有30%MTBE的环己烷)纯化。获得了2.32g纯产物(纯度:96%;蒸气压为0.00133mbar)。
c.)琥珀酸双(3-(硝基氧基)丙基)酯(I-c)的制备
将5.14g的3-硝基氧基丙醇溶解在20ml的二氯甲烷中,并加入2.319ml的琥珀酰二氯。将混合物在23℃下搅拌16小时。添加固体碳酸钾直至看不到二氧化碳的进一步散出,然后将混合物过滤,将滤渣用丙酮洗涤,并将滤液减压浓缩,得到6.35g几乎无色的液体。将粗产物溶解在50ml叔丁基甲基醚中,并用水洗涤10次(每次50ml)。将有机相用硫酸镁干燥并减压蒸发,得到了5.7g琥珀酸双(3-(硝基氧基)丙基)酯(产率:83%;纯度:94.7%,蒸气压:0.00133mbar)。
实施例2:用于甲烷生产的体外测试
使用改良版的“霍恩海姆饲用价值测试(Hohenheim Forage value Test,HFT)”来测试特定化合物对通过这种体外系统模仿的瘤胃功能的影响。
原理:将饲料(即TMR)(300mg)同瘤胃液与适当的缓冲液混合物的组合物(即瘤胃液缓冲液混合物:25ml)和浓度如表2所概述的待测物质(将待测抑制剂在乙醇中稀释至达到干物质的相应浓度为50μl)一起放入注射器中。将该溶液在39℃下孵育8小时。测量产生气体的量并将其代入用于转化的公式中。在孵育后,用GC测量气体的组成。
试剂:
大量元素溶液:
-6.2g磷酸二氢钾(KH2PO4)
-0.6g七水合硫酸镁(MgSO4*7H2O)
-9ml浓磷酸(1mol/l)
-溶于蒸馏水至1l(pH为约1.6)
缓冲溶液:
-35.0g碳酸氢钠(NaHCO3)
-4.0g碳酸氢铵((NH4)HCO3)
-溶于蒸馏水至1l
微量元素溶液:
-13.2g二水合氯化钙(CaCl2*2H2O)
-10.0g四水合氯化锰(II)(MnCl2*4H2O)
-1.0g六水合氯化钴(II)(CoCl2*6H2O)
-8.0g氯化铁(III)(FeCl3*6H2O)
-溶于蒸馏水至100ml
钠盐溶液:
-100mg钠盐
-溶于蒸馏水至100ml
还原溶液:
-首先将3ml氢氧化钠(c=1mol/l),然后427.5mg水合硫化钠(Na2S*H2O)添加到71.25ml的H2O中。
-溶液必须紧接在添加到培养基溶液中之前制备好
工序:
样品称量:
将TMR(44%的精饲料、6%的干草、37%的玉米青贮料和13%的牧草青贮料)过筛至1mm,并精确称量到注射器中。一次运行含有4个重复,每个重复使用16个注射器并且包括底物对照(其显示在没有测试化合物的影响的情况下的气体产生)、载体对照(其显示在仅有载体(溶剂)(即用于溶解测试化合物的EtOH)存在下的气体产生)和测试样品(在载体中)(其含有如表2所概述的不同浓度的测试物质)。
瘤胃液-缓冲液-混合物(培养基溶液)的制备:
将这些组分按以下次序在Woulff瓶中混合:
-711ml水
-0.18ml微量元素溶液
-355.5ml缓冲溶液
-355.5ml大量元素溶液
将完成的溶液加温至39℃,之后添加1.83ml钠盐溶液并在36℃下添加还原溶液。
当指示剂在持续搅拌和CO2充气下变为无色时,添加瘤胃液(750ml)。
填充注射器、孵育并确定气体体积:
将瘤胃液-缓冲液混合物添加到如上所述制备的含有TMR和待测试的活性物质的玻璃注射器中。然后将注射器在39℃下在温和搅动下孵育8小时。在8小时之后,测量产生的气体的体积,并通过气相色谱法测定气相中甲烷的百分比。
结果
表2概述了不同浓度的根据本发明的各种二羧酸二酯的甲烷抑制效应。
表2
*对比底物对照减少
如从表2可以取得的,根据本发明的二羧酸二酯是高效的产甲烷抑制剂,同时表现出非常低的蒸气压,从而使得它们存储特别稳定。
Claims (15)
2.根据权利要求1所述的二羧酸二酯,其中n是选自1至15的范围的整数,并且X是C1-24亚烷基基团、C2-24亚烯基基团或C6-24亚芳基基团。
3.根据权利要求1或2所述的二羧酸二酯,其中n选自3至9的范围,优选地选自3至6的范围,最优选地n为3。
4.根据权利要求1或3中任一项所述的二羧酸二酯,其中X选自由以下项组成的组:C1-10亚烷基基团、C2-5亚烯基基团和C6-10亚芳基基团。
5.根据权利要求1或3中任一项所述的二羧酸二酯,其中X选自由未取代的C1-5亚烷基基团、未取代的C2-4亚烯基基团、1,2-亚苯基、1,3-亚苯基和1,4-亚苯基组成的组,最优选地选自由未取代的直链C1-3亚烷基基团和伸乙烯基组成的组。
6.根据权利要求1或5中任一项所述的二羧酸二酯,所述二羧酸二酯为琥珀酸双(3-(硝基氧基)丙基)酯、丙二酸双(3-(硝基氧基)丙基)酯和富马酸双(3-(硝基氧基)丙基)酯。
9.至少一种根据权利要求1至6中任一项所述的二羧酸二酯作为动物饲料中的活性化合物以减少源自反刍动物的消化活动的甲烷形成和/或改善反刍动物性能的用途。
10.根据权利要求9所述的用途,其中所述反刍动物选自由牛、山羊、绵羊、长颈鹿、美洲野牛、欧洲野牛、牦牛、水牛、鹿、骆驼、羊驼、美洲驼、角马、羚羊、叉角羚和蓝牛羚组成的组。
11.根据权利要求9或10所述的用途,其中当在代谢室中测量时,以升/千克干物质摄入量计算的反刍动物甲烷产生减少了至少10%。
12.一种饲料组合物或饲料添加剂,所述饲料组合物或饲料添加剂包含至少一种根据权利要求1至6中任一项所述的式(I)的二羧酸二酯。
13.根据权利要求12所述的饲料组合物,所述组合物为矿物质预混物、维生素预混物,或包含维生素和矿物质的预混物或大丸药。
14.一种用于减少源自反刍动物的消化活动的甲烷产生和/或用于改善反刍动物性能的方法,所述方法包括向所述动物口服施用足量的至少一种根据权利要求1至6中任一项所述的式(I)的二羧酸二酯。
15.根据权利要求14所述的方法,其中施用于所述反刍动物的所述至少一种式(I)的二羧酸二酯的量为1mg/kg饲料至10g/kg饲料。
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