Applications of diphenylpropenone compounds in the preparation of animal feed additives.

Abstract

Applications of a diphenylpropenone compound of general formula (I), or a stereoisomer thereof, or a geometric isomer thereof, or a tautomer thereof, or a solvate thereof, or a salt acceptable for feed in the preparation of an animal feed additive or animal feed. Confirmed by animal breeding test, the diphenylpropenone compound, or the stereoisomer thereof, or the geometric isomer thereof, or the tautomer thereof, or the solvate thereof, or the salt acceptable for the feed can be used as the animal feed additive or the animal feed. Animal weight can be effectively increased, survival rates can be enhanced, and the compound has a good effect of improving animal production performance.

Description

Application of diphenylpropenone compounds in the preparation of animal feed additives or animal feed Technical Field

[0001] This invention relates to the field of animal feed technology, and in particular to the application of diphenylpropenone compounds in the preparation of animal feed additives or animal feed. Background Technology

[0002] Diphenylpropenone compounds are widely distributed in nature and are an important class of organic intermediates with a wide range of biological activities.

[0003] Feed additives refer to small or trace amounts of substances added during feed processing, preparation, and use, including nutritional feed additives and general feed additives. General feed additives are small or trace amounts of substances added to feed to ensure or improve feed quality and increase feed utilization. Currently, commonly used general feed additives that effectively and stably improve feed utilization and animal production performance mainly include high-dose copper agents, high-dose zinc agents, feed antibiotics, and chemically synthesized antibacterial agents. However, long-term use of these substances in animal husbandry has significant side effects, such as liver and kidney toxicity, growth inhibition, kidney damage, urinary tract disorders, teratogenicity, mutagenicity, drug resistance, drug residues, and environmental pollution. To ensure animal health and improve the production efficiency of animal husbandry, seeking effective, stable, and safe new feed additives, especially general feed additives, is an urgent problem to be solved in this field.

[0004] Currently, no studies have disclosed the application of diphenylpropenone compounds in feed additives or feed.

[0005] Summary of the Invention

[0006] Therefore, it is necessary to provide an application of diphenylpropenone compounds in the preparation of animal feed additives.

[0007] The use of a diphenylpropenone compound of general formula (I), or its stereoisomer, geometric isomer, tautomer, solvate, or feed-acceptable salt thereof, in the preparation of animal feed additives or animal feed:

[0008]

[0009] Wherein, R1 is selected from OH and Cl-C respectively. 20 Alkyl, OC1-C 20 Alkyl, C(=O)OH, C(=O)OC1-C 20 Alkyl or X; R2 is selected from OH, C1-C respectively. 20 Alkyl, OC1-C 20Alkyl or X; n and m are integers from 0 to 5, and X is F, Cl, Br or I.

[0010] In one embodiment, R1 is selected from OH, OC1-C5 alkyl, C1-C5 alkyl, C(=O)OH or C(=O)OC1-C5 alkyl, F, Cl or Br.

[0011] In one embodiment, R1 is selected from OH, C(=O)OH, OC1-C5 alkyl or Cl.

[0012] In one embodiment, R2 is selected from OH, OC1-C5 alkyl, C1-C5 alkyl, F, Cl or Br.

[0013] In one embodiment, R2 is optionally selected from C1-C5 alkyl, OC1-C5 alkyl or Cl.

[0014] In one embodiment, n≠0.

[0015] In one embodiment, R1 is selected from OH, C(=O)OH or Cl; R2 is selected from C1-C5 alkyl or Cl.

[0016] In one embodiment, the diphenylpropenone compound is selected from the following compounds:

[0017]

[0018]

[0019] The present invention also provides a feed composition comprising a diphenylpropenone compound of general formula (I) used in the above applications, or a stereoisomer, a geometric isomer, a tautomer, a solvate, or a feed-acceptable salt thereof, and one or more of feedable adjuvants, animal feed additives, and animal feed ingredients.

[0020] In one embodiment, the feedable excipient is selected from one or more of a carrier, diluent, excipient, and solvent.

[0021] In one embodiment, the animal feed additive is selected from one or more of nutritional feed additives, general feed additives, and medicated feed additives.

[0022] Compared with the prior art, the present invention has the following beneficial effects:

[0023] This invention demonstrates through animal breeding experiments that diphenylpropenone compounds, or their stereoisomers, geometric isomers, tautomers, solvates, or feed-acceptable salts, when used as animal feed additives or in animal feed, can effectively increase animal weight gain and survival rate, and have a good effect on improving animal production performance. Detailed Implementation

[0024] The application of the diphenylpropenone compounds of the present invention in the preparation of animal feed additives will be further described in detail below with reference to specific embodiments.

[0025] Certain embodiments of the invention will now be described in detail, examples of which are illustrated by the accompanying structural and chemical formulas. The invention is intended to encompass all alternatives, modifications, and equivalents, all of which are included within the scope of the invention as defined in the claims. Furthermore, certain technical features of the invention are clearly visible and are described separately in several independent embodiments, but may also be provided in combination or in any suitable sub-combination in a single embodiment.

[0026] Compounds:

[0027] This invention relates to the use of a diphenylpropenone compound with the structure shown in formula (I), or its stereoisomers, geometric isomers, tautomers, solvates or feed-acceptable salts, in the preparation of feed additives or feed.

[0028]

[0029] Where R1 represents any substituent at the 1-, 2-, 3-, 4-, or 5-position of the benzene ring, and R2 represents any substituent at the 1'-, 2'-, 3'-, 4'-, or 5'-position of the benzene ring. n and m represent the number of substituents of R1 and R2 on the benzene ring, respectively. R1 is OH, C1-C 20 Alkyl, OC1-C 20 Alkyl, C(=O)OH, C(=O)OC1-C 20 Alkyl or X, R2 is OH, C1-C 20 Alkyl, OC1-C 20 Alkyl or X, where n and m are integers from 0 to 5, and X is F, Cl, Br or I.

[0030] Generally, "substituted" means that one or more substituted hydrogen atoms in the given structure are replaced by a specific substituent. A substituted group can have one substituent at each substituted position of the group. When more than one position in the given structural formula can be replaced by one or more substituents of a specific group, the substituents can be substituted at each position in the same or different ways.

[0031] In this invention, "C" a -C b "Alkyl" refers to a straight-chain or branched saturated alkyl group containing a to b carbon atoms, such as methyl, ethyl, propyl, isopropyl, ..., while "C1-C5 alkyl" refers to a straight-chain or branched saturated alkyl group containing 1 to 5 carbon atoms.

[0032] In some embodiments, the number n and m of substituent groups R1 and R2 in diphenylpropenone and its derivatives represented by formula (I) are both 0.

[0033] In some embodiments, R1 of diphenylpropenone and its derivatives represented by formula (I) is OH.

[0034] In some embodiments, R1 of diphenylpropenone and its derivatives represented by formula (I) is OC1-C. 20 alkyl.

[0035] Furthermore, R1 is preferably an OC1-C5 alkyl group.

[0036] Optionally, R1 is an OC1-C5 straight-chain alkyl group, specifically methoxy (OCH3), ethoxy (OCH2CH3), propoxy (O(CH2)2CH3), butoxy (O(CH2)3CH3), or pentoxy (O(CH2)4CH3).

[0037] Alternatively, R1 may be an OC1-C5 branched alkyl group, including but not limited to isopropoxy (OCH2(CH3)2) and isobutoxy (OC(CH3)3).

[0038] In some embodiments, the R1 of diphenylpropenone and its derivatives represented by formula (I) is C1-C. 20 alkyl.

[0039] Furthermore, R1 is preferably a C1-C5 alkyl group.

[0040] Optionally, R1 is a C1-C5 straight-chain alkyl group, specifically methyl (CH3), ethyl (CH2CH3), propyl ((CH2)2CH3), butyl ((CH2)3CH3), or pentyl ((CH2)4CH3).

[0041] Alternatively, R1 may be a C1-C5 branched alkyl group, including but not limited to isopropyl (CH2(CH3)2) and isobutyl (C(CH3)3).

[0042] In some embodiments, R1 of diphenylpropenone and its derivatives represented by formula (I) is C(=O)OH or C(=O)OC1-C20 alkyl.

[0043] Furthermore, R1 is preferably C(=O)OH or C(=O)OC1-C5 alkyl.

[0044] Optionally, when R1 is a C(=O)OC1-C5 alkyl group, it is preferably a C(=O)OC1-C5 straight-chain alkyl group, specifically C(=O)OCH3, C(=O)OCH2CH3, C(=O)O(CH2)2CH3, C(=O)O(CH2)3CH3 or C(=O)O(CH2)3CH3.

[0045] Alternatively, when R1 is a C(=O)OC1-C5 alkyl group, it is preferably a C(=O)OC1-C5 branched alkyl group, including but not limited to C(=O)OCH2(CH3)2 and C(=O)OC(CH3)3.

[0046] In some embodiments, R1 of diphenylpropenone and its derivatives represented by formula (I) is a halogen X, specifically F, Cl, Br or I.

[0047] Furthermore, R1 is preferably Cl.

[0048] In some embodiments, R2 of diphenylpropenone and its derivatives represented by formula (I) is OH.

[0049] In some embodiments, R2 of diphenylpropenone and its derivatives represented by formula (I) is OC1-C. 20 alkyl.

[0050] Furthermore, the R2 is preferably an OC1-C5 alkyl group.

[0051] Optionally, R2 is an OC1-C5 straight-chain alkyl group, specifically methoxy (OCH3), ethoxy (OCH2CH3), propoxy (O(CH2)2CH3), butoxy (O(CH2)3CH3), or pentoxy (O(CH2)4CH3).

[0052] Alternatively, R2 may be an OC1-C5 branched alkyl group, including but not limited to isopropoxy (OCH2(CH3)2) and isobutoxy (OC(CH3)3).

[0053] In some embodiments, the R2 of diphenylpropenone and its derivatives represented by formula (I) is C1-C2. 20 alkyl.

[0054] Furthermore, the R2 is preferably a C1-C5 alkyl group.

[0055] Optionally, R2 is a C1-C5 straight-chain alkyl group, specifically methyl (CH3), ethyl (CH2CH3), propyl ((CH2)2CH3), butyl ((CH2)3CH3), or pentyl ((CH2)4CH3).

[0056] Alternatively, R2 may be a C1-C5 branched alkyl group, including but not limited to isopropyl (CH2(CH3)2) and isobutyl (C(CH3)3).

[0057] In some embodiments, R2 of diphenylpropenone and its derivatives represented by formula (I) is halogen X, specifically F, Cl, Br or I.

[0058] Furthermore, R2 is preferably Cl.

[0059] In some embodiments, the diphenylpropenone and its derivatives represented by formula (I) are multisubstituted derivatives of R1 and / or R2, and n and m are independently selected from 1, 2, 3, 4 or 5.

[0060] Optionally, n and m are the same and are selected from 1, 2, 3, 4 or 5.

[0061] Preparation and purification of compounds:

[0062] The preparation method of diphenylpropenone and its derivatives shown in formula (I) of this invention mainly involves the Claisen-Schmidt condensation reaction, which uses phenyl-substituted derivatives of acetophenone (abbreviated as AB) and phenyl-substituted derivatives of benzaldehyde (abbreviated as BZ) as starting materials to undergo alkaline conditions such as sodium hydroxide for aldol condensation reaction, and the reaction process is shown in formula (II).

[0063]

[0064] It should be clarified that NaOH in formula (Ⅱ) represents sodium hydroxide.

[0065] In some technical solutions, the target product (TM) generated by the reaction process shown in formula (II) above has a configurational transformation of the tautomer as shown in formula (III) under suitable conditions.

[0066]

[0067] When the reactants involved, phenyl-substituted derivatives of acetophenone (abbreviated as AB) and phenyl-substituted derivatives of benzaldehyde react to generate the corresponding diphenylpropenone and its derivatives with rigid structures, the reaction substrate can generate different geometric isomers during the reaction process.

[0068] The aforementioned geometric isomers and tautomers are also included within the scope of this invention.

[0069] The "geometric isomers" involved in this invention refer to compounds with the same chemical structure but different spatial arrangements of atoms or groups. They are stereoisomers, including enantiomers, diastereomers, conformational isomers, geometric isomers, and transisomers. "Enantiomers" are two non-overlapping but mirror-image isomers of a compound. "Diarrheomers" are stereoisomers with two or more chiral neutral molecules that are not mirror images of each other, possessing different physical properties such as melting point, boiling point, spectral properties, and reactivity. Mixtures of non-corresponding isomers can be separated by high-resolution analytical operations such as electrophoresis or chromatography. "Tautomers" are structural isomers with different energies that can interconvert through low energy barriers.

[0070] In some embodiments, the preparation process of diphenylpropenone and its derivatives provided by the present invention also involves the separation, purification, or recrystallization of the reaction products. The reaction products can be obtained as crude products from the reaction system by solvent removal. To obtain solid substances with higher chemical purity and lower impurity content, the crude products are dissolved, crystallized, precipitated, recrystallized, and separated in alcohol solvents, alcohol-water mixed solvents, or other organic solvents suitable for recrystallization under appropriate temperature, light, and mechanical vibration conditions to obtain diphenylpropenone and its derivatives with a specific crystalline state. The diphenylpropenone and its derivatives with a specific 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 hydrates of diphenylpropenone and its derivatives or ethanolic compounds of diphenylpropenone and its derivatives.

[0071] The "solvate" involved in this invention refers to a eutectic association formed by the binding of stoichiometric or non-stoichiometric amounts of solvent molecules through non-covalent intermolecular forces during the contact between the compound and solvent molecules, caused by external and internal conditions. Solvents forming solvates include, but are not limited to, water, acetone, ethanol, methanol, dimethyl sulfoxide, ethyl acetate, acetic acid, and isopropanol. "Hydrate" refers to an association or crystal formed where the solvent molecules are water, that is, a compound in which stoichiometric or non-stoichiometric amounts of water are bound together through non-covalent intermolecular forces.

[0072] The preparation of diphenylpropenone and its derivatives provided by this invention can be further processed by salting out to obtain solid substances with higher chemical purity and lower impurity content. The salting-out method utilizes the principles of acid-base neutralization, acid-base coordination, or acid-base chelation to precipitate amino acid derivatives with corresponding organic bases, inorganic bases, organic acids, or inorganic acids, obtaining feed-acceptable salts. The inorganic acids include, but are not limited to, hydrochlorides, hydrobroms, phosphates, sulfates, nitrates, or combinations thereof. The organic bases include, but are not limited to, ammonia or triethylamine. The inorganic bases include, but are not limited to, sodium hydroxide, potassium hydroxide, magnesium hydroxide, or calcium hydroxide.

[0073] The feed-acceptable salts are salts formed by diphenylpropenone and its derivatives of the present invention with organic bases, inorganic bases, organic acids, or inorganic acids that are non-toxic to animals. "Feed-acceptable" means that the substance or composition must be chemically or toxicologically appropriate in relation to the feed or the farmed animals to which it is consumed.

[0074] In some embodiments, diphenylpropenone and its derivatives are ester derivatives, and the post-treatment salting-out precipitation process forms acid-base coordination salts and / or acid-base chelate salts with inorganic or organic acids, including but not limited to acetates, maleates, succinates, mandelates, fumarates, malonates, malates, 2-hydroxypropionates, pyruvates, oxalates, glycolates, salicylates, glucurons, galactosylates, citrates, tartrates, aspartates, glutamates, benzoates, p-methylbenzoates, cinnamates, p-toluenesulfonates, benzenesulfonates, methanesulfonates, ethanesulfonates, trifluoromethanesulfonates, or combinations thereof.

[0075] This invention relates to the application of diphenylpropenone compounds:

[0076] The diphenylpropenone compounds, or their geometric isomers, tautomers, solvates, or feed-acceptable salts provided by this invention, are used in the preparation of animal feed additives or animal feed.

[0077] The term "animal" in this invention refers to a human or domesticated animal that cannot synthesize organic matter from inorganic matter, can only consume organic matter, and whose life activities include feeding, digestion, absorption, respiration, circulation, excretion, sensation, movement, and reproduction. "Domesticated animals" include poultry, livestock, aquatic animals, and other legally captured animals raised in captivity, including pets such as cats and dogs. The term "livestock" includes, for example, any of pigs, cattle, horses, goats, sheep, deer, and many useful rodents. The term "poultry" includes, for example, chickens, ducks, geese, quails, pigeons, etc. The term "aquatic animals" includes, for example, fish, shrimp, turtles, soft-shelled turtles, etc.

[0078] The diphenylpropenone compounds provided by this invention, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof, are used to prepare non-nutritive additives for improving animal production performance at various growth stages. These animals may be selected from livestock, poultry, aquaculture animals, or pets at various growth stages.

[0079] Furthermore, the livestock include, but are not limited to, pigs, cattle, sheep, horses, rabbits, minks, or donkeys; the poultry include, but are not limited to, chickens, turkeys, ducks, geese, quails, or pigeons; the aquatic animals include, but are not limited to, fish, shrimp, turtles, crabs, soft-shelled turtles, bullfrogs, eels, or loaches; and the pets include, but are not limited to, various subspecies of dogs or cats.

[0080] In one embodiment, a feed additive for improving the production performance of hogs is prepared using the diphenylpropenone compounds provided by the present invention, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof, which improves the average daily weight gain and feed conversion ratio of hogs.

[0081] In another embodiment, feed additives prepared using the diphenylpropenone compounds provided by the present invention, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof, can significantly improve the production performance of broilers or laying hens.

[0082] In another embodiment, the diphenylpropenone compounds provided by the present invention, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof, are used to prepare feed additives that improve the production performance of fish.

[0083] The feed-acceptable salt of the diphenylpropenone compounds provided by this invention, used in the preparation of animal feed additives, is a metal ion salt.

[0084] Optionally, the feed-acceptable salt of the diphenylpropenone compound is a metal ion salt of the diphenylpropenone compound with the structure shown in formula (I).

[0085] Furthermore, when the diphenylpropenone compound with the structure shown in formula (I) contains active H, the metal ion salt is a salt that meets the requirements for feed additive preparation or feed preparation, obtained by exchanging the active H of the diphenylpropenone compound with metal ions.

[0086] Specifically, the metal ions are selected from monovalent, divalent, or trivalent metal ions.

[0087] In some embodiments, the monovalent metal ion is sodium ion (Na(Ⅰ)), potassium ion (K(Ⅰ)) or lithium ion (Li(Ⅰ)).

[0088] In some embodiments, the divalent metal ions are calcium ions (Ca(II), magnesium ions (Mg(II), copper ions (Cu(II), zinc ions (Zn(II), ferrous ions (Fe(II), manganese ions (Mn(II)), cobalt ions (Co(II)) or nickel ions (Ni(II)).

[0089] In one embodiment, the metal ion salt of the diphenylpropenone compound used in the preparation of the animal feed additive is a zinc ion salt, wherein the animal feed additive is an animal organic zinc agent as a high-dose inorganic zinc substitute.

[0090] In one embodiment, the metal ion salt of the diphenylpropenone compound used in the preparation of animal feed additives is a copper ion salt, and the animal feed additive is an organic copper for animals as a substitute for high-dose inorganic copper for animals.

[0091] In one embodiment, the metal ion salt of the diphenylpropenone compound used in the preparation of animal feed additives is an iron ion salt, and the animal feed additive is an iron supplement for animals.

[0092] In some embodiments, the trivalent metal ions are aluminum ions (Al(III), chromium ions (Cr(III)) or iron ions (Fe(III)).

[0093] The feed composition involved in this invention:

[0094] The feed composition includes a diphenylpropenone compound of general formula (I), or a stereoisomer, a geometric isomer, a tautomer, a solvate, or a feed-acceptable salt thereof, as well as one or more of feedable adjuvants, animal feed additives, and animal feed ingredients.

[0095] Furthermore, the feedable excipient is selected from one or more of the following: carrier, diluent, excipient, and solvent.

[0096] The feed involved in this invention refers to products that are industrially processed and manufactured for animal consumption.

[0097] The “composition” involved in this invention refers to a group of compounds comprising one or more compounds as active ingredients.

[0098] The term "comprising" as used in this invention is an open-ended expression, encompassing both the content explicitly referred to in this invention and excluding other aspects.

[0099] The "carrier" involved in this invention refers to a feedable substance capable of carrying active ingredients, improving their dispersibility, and possessing good chemical stability and adsorption properties. This can be an organic or inorganic carrier. The organic carrier is a material rich in crude fiber, including but not limited to corn flour, corn cob flour, wheat bran, rice husk flour, defatted rice bran, rice bran, corn stalk flour, and peanut shell flour. The inorganic carrier is a mineral, mainly divided into calcium salts and silicon oxides, used in the production of trace element premixes, including but not limited to calcium carbonate, silicates, vermiculite, zeolite, and sepiolite.

[0100] The "diluent" involved in this invention refers to a substance that uniformly distributes additive raw materials in a material, diluting high-concentration additive raw materials into low-concentration premixes or premixes. It can separate trace components from each other, reduce interactions between active ingredients, and increase the stability of active ingredients without affecting the physicochemical properties of related substances. It can be either an organic or inorganic diluent. Organic diluents include, but are not limited to, corn flour, degermed corn flour, dextrose (glucose), sucrose, whole wheat flour with bran, roasted soybean flour, wheat middlings, and corn gluten meal; inorganic diluents include, but are not limited to, limestone, calcium dihydrogen phosphate, shell powder, kaolin (white clay), salt, and sodium sulfate.

[0101] The excipients mentioned are wetting agents that induce the inherent viscosity of the material itself, adhesives that bind the material together, disintegrants that break down the whole sheet of material into many fine particles, retention aids that reduce the friction between particles, or anti-adhesion agents that prevent materials from sticking together, including but not limited to magnesium stearate, talc, vegetable oil, magnesium lauryl sulfate, starch, starch paste, water, inorganic salts, dextrin, sugar powder, etc.

[0102] The "solvent" involved in this invention refers to the solvent required to dissolve or disperse solids, including but not limited to water, ethanol, glycerol, etc.

[0103] The animal feed additives mentioned are one or more of the following: nutritional feed additives, general feed additives, or medicated feed additives.

[0104] The aforementioned nutritional feed additives refer to small or trace amounts of substances added to compound feed to balance feed nutrients, improve feed utilization, and directly exert a nutritional effect on animals. These substances include amino acids, amino acid salts and their analogues, vitamins and vitamin-like substances, mineral elements and their complexes (chelates), microbial enzyme preparations, or non-protein nitrogen.

[0105] The aforementioned general feed additives, also known as non-nutritive additives, refer to non-nutritive substances added to feed to improve feed utilization, ensure feed quality and grade, and benefit animal health or metabolism. These include growth promoters, deworming and health care agents, flavoring and palatability enhancers, feed conditioners, feed formulations, feed storage agents, and traditional Chinese medicine additives.

[0106] More specifically, the non-nutritive additives are growth promoters, including but not limited to butyric acid, calcium butyrate, sodium butyrate, tannic acid, p-thymol, p-thymol ester, p-thymol salt, 2-hydroxybenzoic acid, β-acid, β-ester, β-acid salt, hexahydroβ-acid, hexahydroβ-ester, hexahydroβ-acid salt, benzoic acid or calcium benzoate, zinc oxide, zinc sulfate, and zinc chloride.

[0107] In one embodiment, the non-nutritive additive is calcium butyrate.

[0108] In another embodiment, the non-nutritive additive is tannic acid.

[0109] The medicated feed additives include, but are not limited to, veterinary drug premixes that have the effects of preventing animal diseases and promoting animal growth and can be added to feed for a long period of time and are incorporated into carriers or diluents.

[0110] Specifically, the medicated feed additive is a feed antibiotic, which includes, but is not limited to, polymyxin, salinomycin, avilamycin, bacitracin, virginiamycin, naringin, flavomycin, enramycin, kimarimycin, quinethol, oxytetracycline, or chlortetracycline.

[0111] The animal feed ingredients mentioned include grains and their processed products, oilseeds and their processed products, legume seeds and their processed products, tubers and roots and their processed products, other seeds and fruits and their processed products, forage and roughage and their processed products, other plants and algae and their processed products, dairy products and their by-products, terrestrial animal products and their by-products, fish and other aquatic organisms and their by-products, minerals, microbial fermentation products and by-products, and other feed ingredients, etc.

[0112] Uses of feed composition:

[0113] This invention relates to the use of the above-mentioned feed compositions comprising diphenylpropenone compounds, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof.

[0114] In some embodiments, the feed composition comprising a diphenylpropenone compound, or its geometric isomer, its tautomer, its solvate, or its feed-acceptable salt is used in the preparation of an animal feed additive.

[0115] Animal feed additives prepared from feed compositions comprising the aforementioned diphenylpropenone compounds, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof, are livestock feed additives, poultry feed additives, aquaculture animal feed additives, or pet feed additives.

[0116] Specifically, livestock feed additives are prepared using feed compositions comprising the aforementioned diphenylpropenone compounds, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof, wherein the livestock include, but are not limited to, pigs, cattle, sheep, horses, rabbits, mink, etc., at various growth stages.

[0117] Specifically, poultry feed additives are prepared using feed compositions comprising the aforementioned diphenylpropenone compounds, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof, wherein the poultry includes, but is not limited to, chickens, ducks, geese, pigeons, etc. at various growth stages.

[0118] Specifically, feed additives for aquaculture animals are prepared using feed compositions comprising the aforementioned diphenylpropenone compounds, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof. The aquaculture animals include, but are not limited to, fish, shrimp, crabs, turtles, eels, etc., at various growth stages.

[0119] Specifically, pet food additives are prepared using feed compositions comprising the aforementioned diphenylpropenone compounds, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof, wherein the pets include, but are not limited to, artificially bred dogs or cats.

[0120] In some embodiments, animal feed additives prepared from compositions of the diphenylpropenone compounds, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof, are premixes, compound premixes, aqueous solutions, or granules.

[0121] In some embodiments, a feed composition comprising the aforementioned diphenylpropenone compound, or its geometric isomer, its tautomer, its solvate, or its feed-acceptable salt is used in the preparation of animal feed.

[0122] Animal feed prepared using the feed composition comprising diphenylpropenone compounds, or their geometric isomers, tautomers, or solvates, or their feed-acceptable salts, is livestock feed, poultry feed, aquaculture animal feed, or pet feed.

[0123] Specifically, livestock feed is prepared using the feed composition comprising diphenylpropenone compounds, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof, including but not limited to pigs, cattle, sheep, horses, rabbits, mink, etc. at various growth stages.

[0124] Specifically, poultry feed is prepared using the feed composition comprising diphenylpropenone compounds, or their geometric isomers, or their tautomers, or their solvates, or their feed-acceptable salts, wherein the poultry includes, but is not limited to, chickens, ducks, geese, pigeons, etc. at various growth stages.

[0125] Specifically, the feed for aquaculture animals is prepared using the feed composition comprising diphenylpropenone compounds, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof. The aquaculture animals include, but are not limited to, fish, shrimp, crabs, turtles, eels, etc., at various growth stages.

[0126] Specifically, pet food is prepared using the feed composition comprising a diphenylpropenone compound, or its geometric isomer, or its tautomer, or its solvate, or its feed-acceptable salt, wherein the pets include, but are not limited to, artificially bred dogs or cats.

[0127] In some embodiments, feeds prepared from feed compositions comprising diphenylpropenone compounds, or their geometric isomers, tautomers, or solvates, or their feed-acceptable salts, are single feeds, concentrated feeds, compound feeds, compound premixes, or concentrate supplements.

[0128] Specifically, the compound feed mentioned is a complete compound feed.

[0129] Methods to improve the production performance of farmed animals:

[0130] In some feeding practices, farmers administer feed additives containing diphenylpropenone compounds, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof, to animals in combination with their feed, which can significantly improve animal production performance.

[0131] In some embodiments, the feed additive is a premix, compound premix, granules, or aqueous solution, which is mixed with animal feed and then consumed by the animals.

[0132] The animals mentioned are livestock, poultry, aquatic animals, or pets.

[0133] Specifically, the livestock include, but are not limited to, pigs, cattle, sheep, horses, rabbits, minks, etc. at various growth stages; the poultry include, but are not limited to, chickens, ducks, geese, pigeons, etc. at various growth stages; the aquatic animals include, but are not limited to, fish, shrimp, crabs, turtles, eels, etc. at various growth stages; and the pets include, but are not limited to, artificially raised dogs or cats.

[0134] In one embodiment, farmers feed weaned piglets a feed additive containing a diphenylpropenone compound, or its geometric isomer, or its tautomer, or its solvate, or its feed-acceptable salt, together with the feed, which significantly improves the average daily weight gain and feed conversion ratio of the weaned piglets.

[0135] In one embodiment, farmers feed broilers a feed additive containing a diphenylpropenone compound, or its geometric isomer, or its tautomer, or its solvate, or its feed-acceptable salt, to the feed, which significantly reduces the feed conversion ratio and improves the feed conversion rate of the broilers.

[0136] In one embodiment, fish farmers feed fish with a feed additive containing a diphenylpropenone compound, or its geometric isomer, or its tautomer, or its solvate, or its feed-acceptable salt.

[0137] In one embodiment, farmers feed puppies a feed additive containing a diphenylpropenone compound, or its geometric isomer, or its tautomer, or its solvate, or its feed-acceptable salt, together with their feed.

[0138] In other feeding practices, farmers feed animals a feed composition containing diphenylpropenone compounds, or their geometric isomers, tautomers, solvates, or feed-acceptable salts thereof, which can significantly improve animal production performance.

[0139] Optionally, the feed composition is a feed additive premix, a feed additive compound premix, a granule, or an aqueous solution, which is given to animals in combination with feed.

[0140] In one embodiment, the feed composition is a feed additive premix.

[0141] In one embodiment, the feed composition is a feed additive compound premix.

[0142] Optionally, the feed composition is a concentrated feed, compound feed, compound premix, or concentrate supplement, which is directly fed to animals as animal feed.

[0143] In one embodiment, the feed composition is a complete compound feed.

[0144] Aquaculture experiment:

[0145] The diphenylpropenone and its derivatives involved in the aquaculture trials are shown in Table 1.

[0146] Table 1 List of Diphenylpropenone and its Derivatives

[0147]

[0148] Example B1 Effects of diphenylpropenone and its derivatives on the production performance of hogs

[0149] Three hundred 65-day-old Duroc-Landrace-Large White crossbred lean-type piglets of similar weight were randomly divided into 10 treatment groups, with 3 replicates per group and 10 piglets per replicate, half male and half female. The pigpens and equipment were disinfected before the experiment. During the experiment, the pigs were housed separately in the same pen under the same feeding and management conditions. The pigs had free access to feed and water, and were fed twice daily. Each experimental group was divided into a control group and experimental groups II-II. The control group received only a basal diet, while experimental groups II-II received diets supplemented with 500 ppm of different diphenylpropenone and its derivatives, as shown in Table 2. No additional antioxidants or growth promoters were added to any experimental group throughout the feeding process. The experiment lasted 28 days. At 93 days of age, piglets were weighed after a 12-hour period without interruption of feeding and water supply, and the average daily feed intake (ADFI, g / d*piglets), average daily weight gain (ADG, g / d*piglets), and feed conversion ratio (FCR) were calculated for each experimental group. The calculation formula is as follows:

[0150] Average daily feed intake = (Total feed intake - Leftover feed) / (Number of days in the trial × Number of pigs per replicate);

[0151] Average daily weight gain = (average weight at the end of the trial - average weight at the beginning of the trial) / number of trial days;

[0152] Feed conversion ratio = average daily feed intake / average daily weight gain.

[0153] The experimental results are shown in Table 2. The effects of the test products on the production performance of the experimental pigs were assessed from three aspects: feed intake, weight gain, and feed conversion ratio. The results show that the test products had no significant effect on the feed intake of the experimental pigs; however, the average daily weight gain of each experimental group increased to varying degrees, regardless of whether the feed intake was less than that of the control group, with the most significant increase observed in experimental group VII; and the feed conversion ratio decreased by approximately 3% to 5% in each experimental group compared to the control group.

[0154] Table 2. Results of the effects of diphenylpropenone and its derivatives on the production performance of piglets.

[0155]

[0156] Example B2 Effects of diphenylpropenone and its derivatives on broiler production performance

[0157] The experiment employed a single-factor randomized design, selecting 600 one-day-old, yellow-feathered broiler chickens with similar average weights (50g) and randomly dividing them into 10 treatment groups, with 3 replicates per group, half male and half female, and 20 chickens per replicate. The chicken coop and equipment were disinfected before the experiment. During the experimental period, the chickens were cage-raised under the same conditions in the same coop. The basal diet consisted mainly of corn-soybean meal, with no additional antioxidants or growth promoters added throughout the feeding process. The experimental groups were designated as a control group and Experimental Groups I and II. Experimental Group I served as the control group, receiving only the basal diet. Experimental Groups I and II received 350 ppm of different diphenylpropenone and its derivatives added to their basal diets, as shown in Table 3. The experiment lasted 20 days, with the chickens having free access to water and feed, fed twice daily. For each replicate, chickens were weighed at 21 days of age (feed withheld for 12 hours, water supply continued). Feed consumption was recorded, and the average daily feed intake (ADFI, g / d*bird), average daily weight gain (ADG, g / d*bird), and feed conversion ratio (FCR) of each group were calculated using the following formulas:

[0158] Fertilizer ratio (FCR) = Average daily feed intake / Average daily weight gain.

[0159] The experimental results are shown in Table 3. The results show that the test product had no significant effect on the feed intake of the experimental chickens. Compared with the control group, the average daily weight gain of each experimental group increased by 4.6% to 19.5%, except for experimental group II. The test product improved the feed conversion ratio of each experimental group, which decreased by about 1.3% to 7.2% overall.

[0160] Table 3. Study on the application effects of diphenylpropenone and its derivatives in broiler feed.

[0161]

[0162] Example B4 Application of diphenylpropenone and its derivatives in fish feed

[0163] Grass carp were used in the experimental fish trials, conducted by the Guangzhou Yingsaite Experimental Aquaculture Farm. Healthy, lively, and uniformly sized grass carp fry were raised in large net cages for four weeks before being used in the formal aquaculture trial. The experimental system consisted of floating small net cages. Both the small net cages and the temporary holding net cages were placed in a 3500m² experimental area. 2In a pond with a depth of approximately 1.5m and fully aerated bottom water, 400 grass carp starved for 1 day were randomly divided into 10 groups, with 4 replicates per group and 10 fish per replicate. After weighing, the fish were randomly placed into 40 net cages and fed different experimental feeds. The experimental feeds were prepared in-house, with 250 ppm of different diphenylpropenone and its derivatives added to the basal feed for each group (see Table 4 for grouping). Artificial restricted feeding was used, with the feed amount adjusted weekly. The feeding levels (based on initial body weight) were identical for both groups, with feeding twice daily (7:30 and 15:00), totaling 580g. The experiment lasted for 8 weeks.

[0164] Parameter calculation:

[0165] Weight gain rate (%) = (average final weight - average initial weight) / average initial weight * 100

[0166] Feed conversion ratio = 580 / (average final weight - average initial weight)

[0167] Table 4 shows the results of the growth-promoting experiments on fish by different diphenylpropenone and its derivatives. The results showed that the experimental groups with added diphenylpropenone and its derivatives did not show significant improvement in weight gain and feed conversion rate compared with the control group, but the survival rate of the experimental fish in each experimental group was significantly higher than that of the control group.

[0168] Table 4. Application test groups and results of diphenylpropenone and its derivatives in grass carp feed

[0169]

[0170]

[0171] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0172] The embodiments described above are merely illustrative of several implementations of the present invention, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these all fall within the protection scope of the present invention. Therefore, the protection scope of this invention patent should be determined by the appended claims.

Claims

DEPCT6516 / 08 / 25641. The use of the compound diphenylpropenone, represented by the general formula (I), or stereoisomer, geometric isomer, totomer, solvate or salt acceptable for animal feed in the preparation of animal feed additives or animal feed, (chemical formula) (I), where R1 is chosen alternatively from each of OH, C1-C20 alkyl, OC1-C20 alkyl, C(=O)OH, C(=O)OC1-C20 alkyl or X; R2 is chosen alternatively from each of OH, C1-C20 alkyl, OC1-C20 alkyl or X; n and m are integers from 0 to 5, and X is 1. Use according to claim 1, where R1 is chosen alternatively from each of OH, OC1-C5 alkyl, C1-C5 alkyl, C(=O)OH or C(=O)OC1-C5 alkyl, F, Cl or Br.

3. Use according to claim 2, where R1 is chosen alternatively from each of OH, C(=O)OH, OC1-C5 alkyl or Cl.

4. Use according to claim 1, where R2 is chosen alternatively from each of OH, OC1-C5 alkyl, C1-C5 alkyl, F, Cl or Br.

5. Use according to claim 4, where R2 is chosen alternatively from each of C1-C5 alkyl, OC1-C5 alkyl or Cl. 6.Any use under one of Requisitions 1–5, where n is not equal to 0.

7. Any use under Requisition 6, where R1 is chosen alternatively from each of OH, C(=O)OH or Cl; R2 is chosen alternatively from each of C1–C5 alkyl or Cl8. Any use under one of Requisitions 1–5, where the diphenylpropenone compound is chosen from a group of the following compounds: (chemical formula), and (chemical formula).

9. A feed composition containing a diphenylpropenone compound represented by the general formula (I), or stereoisomer, geometric isomer, totomer, solvate or salt acceptable for the feed of that compound in any use under Requisitions 1–8, and one or more of the types in feedable additives, feed additives, and feed products.10.Animal feed components under claim 9, whereby one or more feed additives are selected from the group of carriers, diluents, pharmaceutical fillers, and solvents; and / or, one or more feed additives are selected from the group of nutritional feed additives, general feed additives, and pharmaceutical feed additives. ----------------------------------------------------------- 1. Use of a digenylpropenone compound represented by the general formula (I), or stereoisomer, geometric isomer, tutohmer, solvate or salt acceptable for animal feed of that compound in the preparation of the feed additive or animal feed, (chemical formula) Where R1 is chosen alternatively based on each of OH, C1-C20 alkyl, OC1-C20 alkyl, C(=O)OH, C(=O)OC1-C20 alkyl, or X; R2 is chosen alternatively based on each of OH, C1-C20 alkyl, OC1-C20 alkyl, or X; n and m are integers from 0 to 5, and X is F, CI, Br, or I2.

1. The use according to claim 1, where R1 is chosen alternatively from each of OH, OC1-C5 alkyl, C1-C5 alkyl, C(=O)OH or C(=O)OC1-C5 alkyl, F, Cl or Br.

2. The use according to claim 2, where R1 is chosen alternatively from each of OH, C(=O)OH, OC1-C5 alkyl or Cl.

3. The use according to claim 1, where R2 is chosen alternatively from each of OH, OC1-C5 alkyl, C1-C5 alkyl, F, Cl or Br.

4. The use according to claim 4, where R2 is chosen alternatively from each of C1-C5 alkyl, OC1-C5 alkyl or Cl.

5. The use according to any one of claims 1 through 5, where n is not equal to 0.

7. The use under Recourse 6, where R is chosen alternatively from each of OH, C(=O)OH or Cl; R2 is chosen alternatively from each of C1-C5 alkyl or Cl.

8. The use under any of Recourses 1 through 5, where a diphenylpropenone compound is chosen from a group comprising the following compounds: (chemical formula) (chemical formula) and (chemical formula). 9.

10. Feed compositions under Reservience 9, where one or more of the feed additives are selected from the group of carriers, diluents, medicated fillers, and solvents; and / or, one or more of the feed additives are selected from the group of nutritional feed additives, general feed additives, and medicinal feed additives;