APPLICATIONS OF DIPHENYLPROPENONE COMPOUNDS IN THE PREPARATION OF ANIMAL FEED ADDITIVES OR ANIMAL FEED
Patent Information
- Authority / Receiving Office
- MX · MX
- Patent Type
- Patents
- Current Assignee / Owner
- XIANFENG PENG
- Filing Date
- 2021-05-14
- Publication Date
- 2026-06-12
AI Technical Summary
Current animal feed additives, such as high levels of copper and zinc agents, antibiotics, and chemically synthesized antimicrobial agents, have significant side effects like toxicity, growth inhibition, and environmental contamination, necessitating the development of a safe and effective alternative.
Utilization of diphenylpropenone compounds, their stereoisomers, tautomers, solvates, or feed-acceptable salts, in the preparation of animal feed additives to enhance animal production performance.
Diphenylpropenone compounds improve animal weight gain, survival rate, and feed conversion efficiency without the adverse effects associated with traditional additives.
Abstract
Description
APPLICATIONS OF DIPHENYLPROPENONE COMPOUNDS IN THE PREPARATION OF FEED ADDITIVES ANIMAL OR ANIMAL FEED TECHNICAL FIELD This disclosure relates to a technical field of animal nutrition, in particular the use of diphenylpropenone compounds in the preparation of animal feed additives or animal feed. BACKGROUND OF THE INVENTION Diphenylpropenone compounds are widely distributed in nature and are an important type of organic intermediate with a wide range of biological activities. Animal feed additives refer to small or trace amounts of substances added during the processing, production, and use of animal feed, including nutritive and general feed additives. General feed additives refer to small or trace amounts of substances mixed with feed to ensure or improve feed quality and increase feed utilization efficiency. Commonly used general feed additives in this field can efficiently and reliably increase feed utilization efficiency and improve animal production performance. These additives primarily include high levels of copper agents, high levels of zinc agents, antibiotics for animal feed, chemically synthesized antimicrobial agents, and so on.However, prolonged use of these substances in the animal husbandry industry has significant side effects, such as hepatic and renal toxicity in animals, growth inhibition, impaired kidney function, urinary tract disorders, teratogenicity, mutagenesis, drug resistance development, drug residues, and environmental pollution, among others. To protect animal health and improve the efficiency of animal husbandry production, finding a new, effective, stable, and safe animal feed additive, especially a general-purpose feed additive, is an urgent problem to be solved in this field. Currently, there is no research that reveals the use of diphenylpropenone compounds in animal feed additives or animal feed. BRIEF DESCRIPTION OF THE INVENTION Based on this, it is necessary to provide a use for a diphenylpropenone compound in the preparation of animal feed additives. This disclosure provides for the use of a diphenylpropenone compound represented by General Formula (I), or an acceptable stereoisomer, geometric isomer, tautomer, solvate, or salt thereof in animal feed preparation of animal feed additives or animal feed, zwcnn / Lznz / E / YiAi wherein each Ri is optionally selected from OH, C1-C20 alkyl, C1-C20 Oalkyl, C(=O)OH, C(=O)O-C1-C20 alkyl or X; each R2 is optionally selected from OH, C1-C20 alkyl, C1-C20 Oalkyl or X; nym are integers from 0 to 5, and X is F, Cl, Br or I. In one embodiment, each Ri is optionally selected from OH, C1-C5 O-alkyl, C1-C5 alkyl, C(=O)OH or C(=O)C1-C5 C(=O)O-alkyl, F, Cl or Br. In one embodiment, each R1 is optionally selected from OH, C(=O)OH, C1-C5 O-alkyl 5 or Cl. In one embodiment, each R2 is optionally selected from OH, C1-C5 O-alkyl, C1-C5 alkyl, F, Cl or Br. In one embodiment, each R2 is optionally selected from C1-C5 alkyl, C1-C5 O-alkyl or Cl. In one realization, n#0. In one embodiment, each R1 is optionally selected from OH, C(=O)OH, or Cl; each R2 is optionally selected from C1-C5 alkyl or Cl. In one embodiment, the diphenylpropenone compound is selected from the group consisting of the following compounds: zwcnn / Lznz / E / YiAi This disclosure further provides a feed composition comprising the diphenylpropenone compound represented by General Formula (I), or the stereoisomer, geometric isomer, tautomer, solvate or feedable salt thereof in the above use, and one or more of a suitable feed accessory, feed additive and feed product. In one embodiment, the appropriate animal feed accessory is one or more selected from the group consisting of a carrier, a diluent, an excipient, and a solvent. In one embodiment, the animal feed additive is one or more selected from the group consisting of a nutritive feed additive, a general feed additive, and a medicated feed additive. Compared to the previous technique, the present disclosure has the following beneficial effects: This disclosure has demonstrated through animal breeding trials that using diphenylpropenone compounds, or stereoisomers, geometric isomers, tautomers, solvates, or acceptable animal feed salts thereof as animal feed additives or animal feed additives, can effectively increase animal weight, improve survival rate, and have a good effect on improving animal production performance. DETAILED DESCRIPTION OF THE ACHIEVEMENTS The use of the diphenylpropenone compounds of this disclosure in the preparation of animal feed additives will be further described in detail below with reference to specific examples. Some embodiments of this disclosure are described in detail herein, with examples illustrated by the accompanying structural and chemical formulas. This disclosure is intended to cover all substituted, modified, and equivalent technical solutions, all of which fall within the scope of this disclosure as defined by the claims. Furthermore, certain technical features of this disclosure are described separately in multiple independent embodiments for clarity, but may also be provided in combination or any suitable subcombination in a single example. Compound: This disclosure relates to the use of a diphenylpropenone compound represented by Formula (I), or an acceptable stereoisomer, geometric isomer, tautomer, solvate or salt thereof in animal feed preparation of feed additives or feed. Formula (I) zwcnn / Lznz / E / YiAi Where, Ri represents any substituent group in position 1, position 2, position 3, position 4 or position 5 of the corresponding benzene ring, R2 represents any substituent group at position 1', position 2', position 3', position 4' or position 5' of the corresponding benzene ring, and nym represent the number of groups substituted by R1 and R2 on the benzene ring, respectively. R1 is OH, CI-C20 alkyl, C1-C20 O-alkyl, C(=O)OH, C(=O)O-C1-C20 alkyl or X, R2 is OH, C1-C20 alkyl, C1-C20 O-alkyl or X, nym are integers from 0 to 5, and X is F, Cl, Bro I. Generally, substituted means that one or more of the replaceable hydrogen atoms in the given structure are replaced by specific substituents. A substituted group can be formed by replacing each replaceable position with a substituent group. When more than one position in the given structural formula can be substituted by one or more specific substituents, the substituent groups at each position may be the same or different. In this disclosure, Ca-Cb alkyl means a linear or branched saturated alkyl containing from a to b carbon atoms, such as methyl, ethyl, propyl, isopropyl, etc. For example, C1-C5 alkyl means a linear or branched saturated alkyl containing from 1 to 5 carbon atoms. In some embodiments, the nym numbers of the R1 and R2 substituent groups in the diphenylpropenone represented by Formula (I) and derivatives thereof are simultaneously 0. In some embodiments, R1 in diphenylpropenone represented by Formula (I) and derivatives thereof is OH. In some embodiments, R1 in diphenylpropenone represented by Formula (I) and derivatives thereof is C1-C20 O-alkyl. In further embodiments, said R1 is preferably C1-C5 O-alkyl. zb / cnn / i ζηζ / Β / γίΛΐ Optionally, said Ri is linear C1-C5 O-alkyl, specifically a methoxy group (OCH3), an ethoxy group (OCH2CH3), a propoxy group (O(CH2)2CH3), a butoxy group (O(CH2)3CH3), or a pentyloxy group (O(CH2)4CH3). Optionally, in addition, said R1 is a branched C1-C5 O-alkyl, including, but not limited to, an isopropoxy group (OCH2(CH3)2), and an isobutoxy group (OC(CH3)3). In some embodiments, R1 in diphenylpropenone represented by Formula (I) and derivatives thereof is C1-C20 alkyl. In further embodiments, said R1 is preferably C1-C5 alkyl. Optionally, said R1 is linear C1-C5 alkyl, specifically methyl (CH3), ethyl (CH2CH3), propyl ((CH2)2CH3), butyl ((CH2)3CH3), or pentyl ((CH2)4CH3). Optionally, in addition, said R1 is a branched C1-C5 alkyl, including, but not limited to, an isopropyl group (CH2(CH3)2), and an isobutyl group (C(CH3)3). In some embodiments, R1 in diphenylpropenone represented by Formula (I) and derivatives thereof is C(=O)OH or C(=O)O-C1-C20 alkyl. In further embodiments, said R1 is preferably C(=O)OH or C(=O)O C1-C5 alkyl. Optionally, when said R1 is C(=O)O-C1-C5 alkyl, it is preferably linear C(=O)O-C1-C5 alkyl, specifically, C(=O)OCH3, C(=O))OCH2CH3, C(=O)O(CH2)2CH3, C(=O)O(CH2)3CH3 or C(=O)O(CH2)4CH3. Optionally, when said R1 is C(=O)O-C1-C5 alkyl, it is preferably branched C(=O)O-C1-C5 alkyl, including, but not limited to, C(=O)OCH2(CH3)2 and C(=O)OC(CH3)3. In some embodiments, R1 in diphenylpropenone represented by Formula (I) and derivatives thereof is halogen X, specifically, F, Cl, Br or I. In further embodiments, said R1 is preferably Cl. zwcnn / Lznz / E / YiAi In some embodiments, R2 in diphenylpropenone represented by Formula (I) and derivatives thereof is OH. In some embodiments, R2 in diphenylpropenone represented by Formula (I) and derivatives thereof is C1-C20 O-alkyl. In further embodiments, said R2 is preferably C1-C5 O-alkyl. Optionally, said R2 is linear C1-C5 O-alkyl, specifically, a methoxy group (OCH3), an ethoxy group (OCH2CH3), a propoxy group (O(CH2)2CH3), a butoxy group (O(OH2)3OH3), or a pentyloxy group (O(CH2)4CH3). Optionally, said R2 is a branched C1-C5 O-alkyl, including, but not limited to, an isopropoxy group (OCH2(CH3)2), and an isobutoxy group (OC(CH3)3). In some embodiments, R2 in diphenylpropenone represented by Formula (I) and derivatives thereof is C1-C20 alkyl. In further embodiments, said R2 is preferably C1-C5 alkyl. Optionally, said R2 is linear C1-C5 alkyl, specifically, methyl (CH3), ethyl (CH2CH3), propyl ((OH2)2OH3), butyl ((OH2)3OH3), or pentyl ((OH2)4OH3). Optionally, in addition, said R2 is a branched C1-C5 alkyl, including, but not limited to, an isopropyl group (CH2(CH3)2), and an isobutyl group (C(CH3)3). In some embodiments, R2 in diphenylpropenone represented by Formula (I) and derivatives thereof is halogen X, specifically, F, OI, Br or I. In further embodiments, said R2 is preferably OI. In some embodiments, the diphenylpropenone represented by Formula (I) and derivatives thereof are polysubstituted derivatives of R1 and / or R2, and each nym is selected from 1, 2, 3, 4 or 5. Optionally, nym are equal, and are selected from 1, 2, 3, 4 or 5. Preparation and purification of the compounds: The preparation process for diphenylpropenone represented by zwcnn / Lznz / E / YiAi Formula (I) and derivatives thereof in this disclosure primarily involve the Claisen-Schmidt condensation reaction. In the Claisen-Schmidt condensation reaction, the phenyl-substituted acetophenone derivative (abbreviated AB) and the phenyl-substituted benzaldehyde derivative (abbreviated BZ) are used as starting materials to carry out an aldol condensation reaction under alkaline conditions such as sodium hydroxide. The reaction procedure is as shown in Equation (II). Equation (II) TM zwcnn / Lznz / E / YiAi To be clear, NaOH in Equation (II) represents sodium hydroxide. In some technical solutions, the target material (TM) generated by the reaction procedure shown in Equation (II) above has a tautomer configuration transformation shown in Equation (III) under suitable conditions. TM' Equation (III) When the corresponding diphenylpropenone and derivatives thereof generated from the reaction of the reactive materials involved, the phenyl-substituted acetophenone derivative (abbreviated as AB) and the phenyl-substituted benzaldehyde derivative have a rigid structure, the reaction substrate can generate different geometric isomer products during the reaction. The aforementioned geometric isomer and tautomer are also included within the scope of implementation of this disclosure. The geometric isomer involved in this disclosure refers to a compound that has the same chemical structure but a different arrangement of atoms or groups in space, including one of the stereoisomers, such as an enantiomer, a diastereomer, a conformational isomer, a geometric isomer, and an atropisomer, and the like. An enantiomer refers to two isomers of a compound that are non-overlapping but are mirror images of each other. A diastereomer refers to a stereoisomer that has two or more chiral centers and whose molecules are not mirror images of each other, and has different physical properties, such as melting point, boiling point, spectral properties, and reactivity. Diastereomeric mixtures can be separated by high-resolution analytical operations such as electrophoresis or chromatography.A tautomer refers to constitutional isomers that have different energies that can be interconverted across a low-energy barrier. In some embodiments, the process for preparing diphenylpropenone and its derivatives provided in this disclosure also involves a process for separating, purifying, or recrystallizing the reaction products. The reaction products can be obtained as crude products from the reaction system by an elimination process. 7b / cnn / i ζηζ / Β / γίΛΐ of the solvent. To obtain solid substances with greater chemical purity and a lower impurity content, the crude products are dissolved, crystallized, precipitated, or recrystallized and separated in alcoholic solvent, mixed alcohol-water solvent, or other organic solvents that can be used for recrystallization of the product under suitable conditions of temperature, light, and mechanical vibration, to obtain diphenylpropenone and its derivatives in a specified crystalline state. Diphenylpropenone and its derivatives in a specified crystalline state are crystals of diphenylpropenone and its derivatives or solvates of diphenylpropenone and its derivatives. The solvates of diphenylpropenone and its derivatives can be selected from diphenylpropenone hydrates and their derivatives or diphenylpropenone ethanolates and their derivatives. The solvate referred to in this disclosure means a eutectic association compound formed by the bonding of solvent molecules chemically equivalent or not chemically equivalent to the compound of this disclosure through non-covalent intermolecular forces under external and internal conditions during contact between the compound of this disclosure and the solvent molecules. Solvents for forming solvates include, but are not limited to, solvents such as water, acetone, ethanol, methanol, dimethyl sulfoxide, ethyl acetate, acetic acid, and isopropanol, or similar solvents. The hydrate refers to an association compound or crystal formed when the solvent molecule is water; that is, a compound formed by the bonding of chemically equivalent or not chemically equivalent water through non-covalent intermolecular forces. To obtain solid substances with greater chemical purity and a lower impurity content, the preparation of diphenylpropenone and its derivatives provided by this disclosure may further involve a salting process. The salting process is a salt precipitation process of amino acid derivatives and the corresponding organic bases, inorganic bases, organic or inorganic acids using the principle of the acid-base neutralization process, the acid-base coordination process, or the acid-base chelation process, to obtain salts acceptable for animal feed. Inorganic acids include, but are not limited to, hydrochloride, hydrobromide, phosphate, sulfate, nitrate, or a combination thereof. Organic bases include, but are not limited to, ammonia or triethylamine.Inorganic bases include, but are not limited to, sodium hydroxide, potassium hydroxide, magnesium hydroxide, or calcium hydroxide. Acceptable salts for animal feed are salts formed from diphenylpropenone and its derivatives as described in this disclosure and an organic base, an inorganic base, an organic acid, or an inorganic acid that is non-toxic to animals. "Acceptable for animal feed" means that the substance or composition must be chemically or toxicologically suitable and is related to the feed being formulated or the farm animals that consume it. In some embodiments, diphenylpropenone and its derivatives are ester derivatives that form an acid-base coordination salt and / or an acid-base chelated salt with an inorganic or organic acid in the subsequent salt precipitation procedure. Organic acids include, but are not limited to, acetate, maleate, succinate, mandelate, fumarate, malonate, malate, 2-hydroxypropionate, pyruvate, oxalate, glycolate, salicylate, glucuronate, galactitolate, citrate, tartrate, aspartate, glutamate, benzoate, p-methylbenzoate, cinnamate, p-toluenesulfonate, benzenesulfonate, methanesulfonate, ethanesulfonate, triflate, or a combination thereof. Use of the diphenylpropenone compound involved in this disclosure: zwcnn / Lznz / E / YiAi The diphenylpropenone compound or the geometric isomer, tautomer, solvate or feed-acceptable salt thereof provided by this disclosure is used in the preparation of animal feed additives or animal feed. The animal involved in this disclosure refers to a person or farm animal that cannot synthesize inorganic substances into organic substances and can only use organic substances as food for vital activities such as ingestion, digestion, absorption, respiration, circulation, excretion, sensation, movement, and reproduction. Farm animal includes poultry, cattle, aquaculture animals, and other animals that are artificially fed and legally captured, including pets such as cats and dogs. The term livestock includes any of, for example, a pig, cattle, horses, goats, sheep, deer, and many useful rodents. The term poultry includes, for example, chickens, ducks, geese, quail, pigeons, and the like. The term aquaculture animal includes, for example, fish, shrimp, turtles, arachnos, and the like. The diphenylpropenone compound, or its geometric isomer, tautomer, solvate, or feed-acceptable salt provided herein, is used to prepare non-nutritive feed additives to enhance the production performance of animals at various growth stages. The animals may be selected from cattle, poultry, aquaculture animals, or pets at various growth stages. Likewise, livestock includes, but is not limited to, pigs, cattle, sheep, horses, rabbits, minks or donkeys; poultry includes, but is not limited to, chickens, turkeys, ducks, geese, quail or pigeons; and aquaculture animals include, but are not limited to, fish, shrimp, turtles, crabs, amphibians, bullfrogs, eels or loaches; and pets include, but are not limited to, dogs or cats of various subspecies. In one embodiment, the diphenylpropenone compound, or the geometric isomer, tautomer, solvate, or feed-acceptable salt thereof provided herein, is used to prepare feed additives intended to improve the production performance of fattening pigs, having an enhancing effect on daily weight gain and feed conversion efficiency of fattening pigs. In another embodiment, the diphenylpropenone compound, or the geometric isomer, tautomer, solvate, or feed-acceptable salt thereof provided herein, is used to prepare feed additives that can significantly improve the production performance of broiler chickens or laying hens. In one embodiment, the diphenylpropenone compound, or the geometric isomer, tautomer, solvate, or feed-acceptable salt thereof provided herein is used to prepare feed additives intended to enhance fish production performance. The acceptable animal feed salt of the diphenylpropenone compound provided by this disclosure used in the preparation of animal feed additives is a salt of a metal ion. Optionally, the acceptable animal feed salt of the diphenylpropenone compound is a metal ion salt of the diphenylpropenone compound having the structure represented by Formula (I). Likewise, when the diphenylpropenone compound having the structure represented by Formula (I) contains active H, the metal ion salt is a salt obtained by exchanging the active H of the diphenylpropenone compound with metal zwcnn / Lznz / E / YiAi ions that meet the requirements for the preparation of animal feed additives or feedstuffs. Specifically, the metal ion salt is selected from a monovalent metal ion, a divalent metal ion, or a trivalent metal ion. In some embodiments, the monovalent metal ion is a sodium ion (Na(l)), a potassium ion (K(l)) or a lithium ion (Li(l)). In some embodiments, the divalent metal ion is a calcium ion Ca(ll), a magnesium ion Mg(ll), a copper ion Cu(ll), a zinc ion Zn(ll), a ferrous ion Fe(ll), a manganese ion Mn(ll), a cobalt ion Co(ll) or a nickel ion Ni(ll). In one embodiment, the metal ion salt of the diphenylpropenone compound used in the preparation of the animal feed additives is a zinc ion salt, and the animal feed additive is an organic zinc agent for animals as an alternative to a high level of inorganic zinc. In one embodiment, the metal ion salt of the diphenylpropenone compound used in the preparation of the animal feed additives is a salt of a copper ion, and the animal feed additive is an organic copper agent for animals as an alternative to a high level of inorganic copper. In one embodiment, the metal ion salt of the diphenylpropenone compound used in the preparation of the animal feed additives is a salt of an iron ion, and the animal feed additive is an iron supplement for animals. In some embodiments, the trivalent metal ion is an aluminum ion Al(l11), a chromium ion Cr(lll) or an iron ion Fe(lll). Feed composition involved in this disclosure: The feed composition comprises the diphenylpropenone compound represented by General Formula (I), or the stereoisomer, geometric isomer, tautomer, solvate or feedable salt thereof, and one or more of a suitable feed accessory, feed additive and feed product. Likewise, the appropriate accessory for animal feeding is one or more selected from the group consisting of a carrier, a diluent, an excipient, and a solvent. The feed involved in this disclosure refers to a product that is industrially processed and manufactured for animal consumption. The composition involved in this disclosure refers to a set of compounds comprising one or more compounds as effective ingredients. The term "comprising" mentioned in this disclosure is an open-ended expression that includes the content explicitly stated in this disclosure, but does not exclude other content. The carrier referred to in this disclosure is a substance suitable for animal feed that can transport active ingredients, improving their dispersibility, and that has good stability and chemical adsorption, including an organic carrier and an inorganic carrier. The organic carrier is a material containing a batch of crude fiber, including, but not limited to, cornmeal, corn cob meal, wheat bran, rice hull meal, defatted rice bran, rice bran and hulls, corn stalk meal, peanut shell meal, and similar materials. The inorganic carrier is a mineral, primarily composed of calcium salts and silicon oxides, used in the production of a trace element premix, including, but not limited to, calcium carbonate, silicates, vermiculite, zeolite, sepiolite, and similar materials. The diluent referred to in this disclosure means a substance that evenly distributes the additive raw materials in the material, dilutes high concentrations of the additive raw materials in a premixed agent or low-concentration premix, which can separate trace components from each other and reduce the interaction between active ingredients to increase the stability of the active ingredients without altering the physical and chemical properties of the related substances, including an organic diluent or an inorganic diluent. Organic diluents include, but are not limited to, corn flour, degerminated corn flour, dextrose (glucose), sucrose, manna-crup with bran, fried soybean meal, middlings, corn gluten meal, and similar substances.The inorganic thinner includes, but is not limited to, limestone, calcium dihydrogen phosphate, shell powder, kaolin (porcelainite), table salt, and sodium sulfate. An excipient is a wetting agent that induces the inherent viscosity of a substance, a binder that binds substances together, a disintegrant that breaks the entire sheet of a substance into many fine particles, a retention aid that reduces friction between particles, or an antiblocking agent that prevents the adhesion of the material, including, but not limited to, magnesium stearate, talc, vegetable oil, magnesium lauryl sulfate, starch, starch slurry, water, inorganic salt, dextrin, powdered sugars, and the like. The solvent involved in this disclosure refers to a solvent necessary to dissolve or disperse solids, including, but not limited to, water, ethanol, glycerin, and the like. An animal feed additive is one or more of a nutritive feed additive, a general feed additive, or a medicated feed additive. A feed nutrient additive refers to small amounts of substances or trace substances that are added to compound feeds to balance the nutrients in the feed, improve feed utilization and directly exert nutritional effects on animals, including amino acids, amino acid salts and analogues thereof, a vitamin and vitamins, a mineral element and complexes (chelates) thereof, a microbial enzyme preparation or a non-protein nitrogen. The general feed additive is also called a non-nutritive additive, which refers to some non-nutritive substances that are added to feed to improve feed utilization, ensure feed quality, and are beneficial to animal health or metabolism, including growth promoters, insect repellents and health care agents, flavoring and attractant agents, feed texturizer, feed modulator, feed storage agent, and Chinese herbal medicine additive. More specifically, the non-nutritive additive is a growth promoter, including, but not limited to, butyric acid, calcium butyrate, sodium butyrate, tannic acid, p-thymol, p-thymol ester, p-thymol salt, 2-dihydroxybenzoic acid, β-acid, β-acid ester, β-acid salt, hexahydro-β-acid, hexahydro-β-acid ester, hexahydro-β-acid salt, benzoic acid or calcium benzoate, zinc oxide, zinc sulfate, and zinc chloride. In one embodiment, the non-nutritive additive is calcium butyrate. In another embodiment, the non-nutritive additive is tannic acid. Medicated feed additives include, but are not limited to, premixed materials for veterinary drugs that have the functions of preventing animal diseases and promoting animal growth, and can be added to feed for an extended period of time and can be incorporated with carriers or diluents. Specifically, the medicated feed additive is an antibiotic for animal feed, including, but not limited to, polymyxin, salinomycin, avilamycin, bacitracin, virginiamycin, nosiheptide, flavomycin, enramycin, kitasimicin, olaquindox, oxytetracycline, or aureomycin. Animal food product is a food substance such as cereals and processed cereal products, oilseeds and processed oilseed products, pulses and processed pulse products, tubers, tuberous roots and processed tuberous root products, other seeds and fruit products and processed fruit products, fodder grass, coarse fodder and processed coarse fodder products, other vegetables, algae and processed algae products, dairy products and by-products thereof, terrestrial animal products and by-products thereof, fish, other aquatic organisms and by-products thereof, minerals, products and by-products of microbial fermentation, and other food products. Use of feed composition: This disclosure relates to a use of the aforementioned feed composition comprising the diphenylpropenone compound, or the geometric isomer, tautomer, solvate, or salt acceptable in animal feed thereof. In some embodiments, the feed composition comprising the diphenylpropenone compound, or the geometric isomer, tautomer, solvate, or feed-acceptable salt thereof, is used in the preparation of animal feed additives. Animal feed additives prepared using the feed composition comprising the diphenylpropenone compound, or the geometric isomer, tautomer, solvate or salt acceptable in animal feed thereof are animal feed additives for livestock, animal feed additives for poultry, animal feed additives for aquaculture animals or pet food additives. Specifically, the feed composition comprising the diphenylpropenone compound, or its geometric isomer, tautomer, solvate, or feed-acceptable salt, is used in the preparation of animal feed additives for livestock. Livestock includes, but is not limited to, pigs, cattle, sheep, horses, rabbits, mink, and similar animals at various growth stages. Specifically, the feed composition comprising the diphenylpropenone compound, or its geometric isomer, tautomer, solvate, or feed-acceptable salt, is used in the preparation of animal feed additives for poultry. Livestock includes, but is not limited to, chickens, ducks, geese, pigeons, and similar birds at various growth stages. Specifically, the feed composition comprising the diphenylpropenone compound, or its geometric isomer, tautomer, solvate, or feed-acceptable salt, is used in the preparation of animal feed additives for aquaculture. Aquaculture animals include, but are not limited to, fish, shrimp, crabs, scorpionfish, eels, and similar animals at various growth stages. Specifically, feed compositions comprising the diphenylpropenone compound, or its geometric isomer, tautomer, solvate, or feed-acceptable salt, are used in the preparation of feed additives for pets. Pets include, but are not limited to, artificial dog and cat food. In some embodiments, the animal feed additives prepared with the composition comprising the diphenylpropenone compound, or the geometric isomer zwcnn / Lznz / E / YiAi, the tautomer, the solvate or the feed-acceptable salt thereof are premix, multiple premix, trace water or granules. In some embodiments, the feed composition comprising the diphenylpropenone compound, or the geometric isomer, tautomer, solvate, or feed-acceptable salt thereof, is used in the preparation of animal feed. Animal feed additives prepared using the feed composition comprising the diphenylpropenone compound, or the geometric isomer, tautomer, solvate or acceptable animal feed salt thereof are feed for livestock, feed for poultry, feed for aquaculture animals or pet food. Specifically, the feed composition comprising the diphenylpropenone compound, or its geometric isomer, tautomer, solvate, or feed-acceptable salt, is used to prepare feed for livestock. Livestock includes, but is not limited to, pigs, cattle, sheep, horses, rabbits, mink, and similar animals at various growth stages. Specifically, the feed composition comprising the diphenylpropenone compound, or its geometric isomer, tautomer, solvate, or feed-acceptable salt, is used to prepare feed for poultry. Poultry includes, but is not limited to, chickens, ducks, geese, pigeons, and similar birds at various growth stages. Specifically, the feed composition comprising the diphenylpropenone compound, or its geometric isomer, tautomer, solvate, or feed-acceptable salt, is used to prepare feed for aquaculture animals. Aquaculture animals include, but are not limited to, fish, shrimp, crabs, scorpionfish, eels, and similar animals at various growth stages. Specifically, feed compositions comprising the diphenylpropenone compound, or its geometric isomer, tautomer, solvate, or feed-acceptable salt, are used to prepare pet feed. Pet feed includes, but is not limited to, artificial dog and cat food. In some embodiments, feeds prepared using the feed composition comprising the diphenylpropenone compound, or the geometric isomer, tautomer, solvate or feed-acceptable salt thereof are single feeds, concentrated feeds, formula feeds, multiple premixes or concentrated supplements. Specifically, compound feed is a complete formula feed. Procedure to improve the production performance of farm animals: In some embodiments of the feed, the farmer feeds the animals with animal feed additives comprising the diphenylpropenone compound, or the geometric isomer, tautomer, solvate, or feed-acceptable salt thereof along with the feed, which can significantly improve the production performance of the animals. In some embodiments, animal feed additives are a premix, multiple premix, granules, or traces of water, which are mixed with animal feed to feed animals. The animal is livestock, poultry, aquaculture animals, or pets. Specifically, livestock includes, but is not limited to, pigs, cattle, sheep, horses, rabbits, mink, and similar animals at various stages of growth. Poultry includes, but is not limited to, chickens, ducks, geese, pigeons, and similar animals at various stages of growth. Aquaculture animals include, but are not limited to, fish, shrimp, crabs, scorpionfish, eels, and similar animals at various stages of growth. And pets include, but are not limited to, pet food for dogs and cats. In one embodiment, the farmer feeds weaned pigs with animal feed additives comprising the compound diphenylpropenone, or the geometric isomer, tautomer, solvate, or feed-acceptable salt thereof along with the feed, thereby significantly increasing the weight gain rate for average daily gain and feed conversion efficiency of the weaned pigs. In one embodiment, the farmer feeds broiler chickens with animal feed additives comprising the diphenylpropenone compound, or the geometric isomer, tautomer, solvate, or feed-acceptable salt thereof along with the feed, thereby significantly reducing the feed conversion ratio of the broiler chickens and increasing the feed conversion efficiency. In one embodiment, the farmer feeds the fish with animal feed additives comprising the diphenylpropenone compound, or the geometric isomer, tautomer, solvate or feed-acceptable salt thereof along with the feed. In one embodiment, the farmer feeds the puppies with animal feed additives comprising the diphenylpropenone compound, or the geometric isomer, tautomer, solvate or feed-acceptable salt thereof along with the feed. In other embodiments of the feed, the farmer feeds the animals with feed compositions comprising the diphenylpropenone compound, or the zwcnn / Lznz / E / YiAi geometric isomer, tautomer, solvate, or animal feed acceptable salt thereof, which can significantly improve the production performance of the animals. Optionally, the feed composition is a premix of animal feed additives, a multiple premix of animal feed additives, granules or traces of water, which are fed to the animals along with the feed. In one embodiment, the feed composition is a premix of animal feed additives. In one embodiment, the feed composition is a multiple premix of animal feed additives. Optionally, the feed composition is a concentrated feed, a formula feed, a multiple premix or a concentrated supplement, with which the animals are fed directly as animal feed. In one embodiment, the feed composition is a complete formula feed. Breeding trial: Table 1 shows the diphenylpropenone and its derivatives involved in the breeding trial. zwcnn / Lznz / E / YiAi zwcnn / Lznz / E / YiAi Table 1 List of diphenylpropenone and its derivatives 5 z(Ri)n 3' ΓΊ -.Ó 2 ¿ (R2)m Compound ns R1 R2 Compound 1 n=0 m=0 Compound 2 n=0 4'-CH3 Compound 3 3-OH m=0 Compound 4 2-OH 3'-CH3 Compound 5 3-OH, 5-OH 3'-CH3 Compound 6 4-COOH m=0 Compound 7 4-OCH3 4'-OCH3 Compound 8 4-O(CH2)4CH3 4'-O(CH2)4CH3 Compound 9 4-CI 4'-CI Example B1. Effect of diphenylpropenone and its derivatives on the production performance of fattening pigs Three hundred lean piglets of a crossbreed (Duroc, Landrace, and Large Yorkshire), 65 days old and of similar body weight, were randomly divided into 10 treatment groups. Each group had three replicates, and each replicate consisted of 10 piglets, half male and half female. The pens and equipment were sterilized before the trial. During the trial, the piglets were fed in separate pens under the same feed and management conditions. The pigs had free access to food and water and were fed twice daily. Each trial group was designated as a control group and trial groups II through X, respectively. The control group was fed only a basal diet, while the trial groups II through X were fed a basal diet. Groups II to X were fed diets supplemented with 500 ppm of various diphenylpropenones and their derivatives, based on the basal diet, as shown in Table 2. No additional antioxidants or growth promoters were added to any of the trial groups during the feeding procedure. The trial period was 28 days, with each replicate being one unit. Pigs were weighed at 93 days of age without water withdrawal but withholding feed for 12 hours to calculate average daily feed intake (ADFI, g / d*head), average daily gain (ADG, g / d*head), and feed conversion ratio (FOR) for each trial group. The calculation formulas are as follows: Average daily feed intake = (total amount of feed-remaining amount of feed) / (days of trial × number of pigs per replicate); Average daily gain = (average weight at the end of the trial - average weight at the beginning of the trial) / days of trial; Feed conversion ratio = average daily feed intake / average daily gain. Table 2 shows the trial results. The effects of the trial samples used in this experiment on the production performance of the trial pigs were evaluated for three aspects: feed intake, weight gain, and feed conversion efficiency. The results show that the trial samples did not have significant effects on the feed intake of the trial pigs. However, the average daily weight gain of each trial group increased to varying degrees, regardless of whether feed intake was lower than that of the control group. This increase was most significant for trial group VII. The feed conversion ratio decreased by approximately 3% to 5% for each trial group compared to the control group. zb / cnn / i ζηζ / Β / γίΛΐ Table 2 Results of the effect of diphenylpropenone and its derivatives on piglet production performance zwcnn / Lznz / E / YiAi Test Group Test Sample ADFI (g / d*head) ADG (g / d*head) FCR Group I - 1601 586 2.733 Group II Compound 1 1584 596 2.658 Group III Compound 2 1597 605 2.64 Group IV Compound 3 1622 621 2.613 Group V Compound 4 1639 626 2.619 Group VI Compound 5 1641 632 2.596 Group VII Compound 6 1635 632 2.588 Group VIII Compound 7 1576 598 2.636 Group IX Compound 8 1608 612 2.627 Group X Compound 9 1585 607 2.611 Example B2. Effect of diphenylpropenone and its derivatives on broiler chicken production performance A single-factor randomized design was adopted for the trial. 600 one-day-old Chinese three-yellow-feather broiler chicks of similar weight (averaging 50 g) were randomly divided into 10 treatment groups. Each group had 3 replicates, half male and half female, with each replicate containing 20 Chinese three-yellow-feather broiler chicks. The poultry house and equipment were sterilized before the trial. During the trial, cage rearing was carried out in the same poultry house under the same feeding and management conditions. The basal diet was primarily coarsely ground corn-soybean meal, and no additional antioxidants or growth promoters were added during the feeding procedure. Each trial group was designated as a control group and trial groups I to X, respectively.In this study, trial group I was the control group fed only the basal diet, while trial groups I to X were fed diets supplemented with 350 ppm of various diphenylpropenones and their derivatives, based on the basal diet. The grouping is shown in Table 3. The trial period was 20 days in total. Broiler chickens in the trial had free access to water and feed and were fed twice daily, with each replicate being one unit. Broiler chickens in the trial were weighed at 21 days of age (with feeding stopped for 12 hours, but water continued) to account for feed intake. Average daily feed intake (ADFI, g / d*number of broiler chickens), average daily gain (ADG, g / d*number of broiler chickens), and feed conversion ratio (FCR) were calculated for each group of broiler chickens in the trial. The calculation formulas are as follows:. Feed conversion ratio (FCR) = average daily feed intake / average daily gain. Table 3 shows the trial results. The results indicate that the trial samples did not have a significant effect on feed intake in the broiler chickens. Regarding the effect on average daily gain, compared to the control group, the average daily gain of each trial group increased by 4.6% to 19.5%, except for trial group II. The trial samples had an improving effect on the feed conversion ratio of each trial group, with an overall decrease of approximately 1.3% to 7.2%. 7b / cnn / l 7Π7 / Β / ΥΙΛΙ zwcnn / Lznz / E / YiAi Table 3. Study of the effects of applying diphenylpropenone and its derivatives to feed for broiler chickens Test sample ADFI (g / d*number of broiler chickens) ADG (g / d*number of broiler chickens) FCR Group I - 30.3 12.8 2.36 Group II Compound 1 30.1 12.9 2.33 Group III Compound 2 32.4 14.1 2.30 Group IV Compound 3 33.8 15.3 2.21 Group V Compound 4 29.5 13.4 2.2 Group VI Compound 5 30.0 13.6 2.2 Group VII Compound 6 31.1 14.2 2.19 Group VIII Compound 7 31.7 13.9 2.28 Group IX Compound 8 30.9 13.6 2.27 Group X Compound 9 32.3 14.5 2.22 Example B4. Use of diphenylpropenone and its derivatives in fish feed The test fish used was grass carp, and the trial was conducted at an aquaculture farm on the test site of Guangzhou Insighter 10 Biotechnology Co., Ltd. Healthy, lively grass carp of similar size were stocked and reared in a large net cage for 4 weeks prior to the formal rearing trial. The experimental system was a small floating net cage. Both the floating net cage and the temporary net cage were placed in a 3500 m² pond on the test site. The pond was approximately 1.5 m deep and the water was fully aerated. During the trial, 400 grass carp that had not been fed for 1 day were randomly divided into 10 groups, with each group having 4 replicates, and each replicate having 10 grass carp. After weighing the total, they were randomly placed in 40 net cages and fed different test feeds.The trial feeds were self-prepared, and 250 ppm of different diphenylpropenones and their derivatives were added to the basic feeds for different trial groups. The groupings are shown in Table 4. An artificial feed restriction was implemented in the trial, and the amount of feed was adjusted once a week. The feeding level (based on initial body weight) for both groups was exactly the same: twice daily (7:30 and 15:00), with a total of 580 g. The trial was conducted for 8 weeks. Calculation of parameters: Rate of weight gain (%) = (average final weight - average initial weight) / average initial weight * 100 Feeding coefficient = 580 / (average final weight - average initial weight) Table 4 shows the results of the growth-promoting trial of different diphenylpropenones and their derivatives on fish. The results show that, compared to the control group, the trial group to which the diphenylpropenones and their derivatives were added did not show significant improvements in weight gain and feed conversion efficiency, but the survival rate of the fish in each trial group was significantly higher than that of the control group. zwcnn / Lznz / E / YiAi zwcnn / Lznz / E / YiAi Table 4 Grouping and results of the trial of application of diphenylpropenones and their derivatives in feed for herbivorous carp Trial Sample Average Initial Weight (g) Average Final Weight (g) Weight Gain Rate (%) Feeding Coefficient Survival Rate (%) Group I - 400 705 76.32 1.90 68 Group II Composite 1 405 714 76.18 1.88 81 Group III Composite 2 411 718 74.67 1.89 83 Group IV Composite 3 392 706 79.98 1.85 89 Group V Composite 4 403 715 77.38 1.86 90 Group VI Composite 5 398 717 80.07 1.82 96 Group VII Composite 6 401 711 77.35 1.87 90 Group VIII Composite 7 397 711 78.97 1.85 88 Group IX Composite 8 409 724 77.07 1.84 87 Group X Composite 9 733 733 77.59 1.81 92 Each of the technical features of the aforementioned embodiments can be combined arbitrarily. To simplify the description, not all possible combinations of each technical feature in the above embodiments are described. However, all combinations of these 10 technical features should be considered as falling within the scope of this disclosure, provided that such combinations do not contradict each other. The realizations mentioned above are merely illustrative of some combinations of the present disclosure, which are specifically and in detail described, but cannot be understood to limit the scope of the present disclosure. It should be noted that, for those generally skilled in the art, some variations and improvements may be made without departing from the concept of this disclosure, and all of these fall within the scope of protection of this disclosure. Therefore, the scope of protection of this disclosure shall be defined in the appended claims.
Claims
1. Use of a diphenylpropenone compound represented by General Formula (I), or a stereoisomer, geometric isomer, tautomer, solvate or feedable salt thereof in the preparation of feed additives or animal feed, zwcnn / Lznz / E / YiAi wherein, each Ri is optionally selected from OH, C1-C20 alkyl, C1-C20 O-alkyl, C(=O)OH, C(=O)O-C1-C20 alkyl or X; each R2 is optionally selected from OH, C1-C20 alkyl, C1-C20 O-alkyl or X; nym are integers from 0 to 5, and X is F, Cl, Br or I.
2. The use according to claim 1, wherein each R1 is optionally selected from OH, C1-C5 O-alkyl, C1-C5 alkyl, C(=O)OH or C(=O)C1-C5 C(=O)O-alkyl, F, Cl or Br.
3. The use according to claim 2, wherein each R1 is optionally selected from OH, C(=O)OH, C1-C5 O-alkyl or Cl.
4. The use according to claim 1, wherein each R2 is optionally selected from OH, C1-C5 O-alkyl, C1-C5 alkyl, F, Cl or Br.
5. The use according to claim 4, wherein each R2 is optionally selected from C1-C5 alkyl, C1-C5 O-alkyl or Cl.
6. Use in accordance with any one of claims 1 to 5, wherein, n^O.
7. The use according to claim 6, wherein each R1 is optionally selected from OH, C(=O)OH or Cl; each R2 is optionally selected from C1-C5 alkyl or Cl.
8. The use according to any one of claims 1 to 5, wherein the diphenylpropenone compound is selected from the group consisting of the following compounds: zwcnn / Lznz / E / YiAi OH O H3C(H2C)40. .O(CH2)4CH; 9. A feed composition comprising the diphenylpropenone compound represented by General Formula (I), or the stereoisomer, geometric isomer, tautomer, solvate or feedable salt thereof for use in any one of claims 1 to 8, and one or more of a suitable feed accessory, feed additive and feed product.
10. The feed composition according to claim 9, wherein the suitable feeding accessory is one or more selected from the group consisting of a carrier, a diluent, an excipient, and a solvent; and / or, the feed additive is one or more selected from the group consisting of a nutritive feed additive, a general feed additive, and a medicated feed additive.