methyl 7-(benzyloxy)-6-butyl-4-oxo-1,4-dihydroquinoline-3-carboxylate
Nequinate
CAS: 13997-19-8
Molecular Formula: C22H23NO4
methyl 7-(benzyloxy)-6-butyl-4-oxo-1,4-dihydroquinoline-3-carboxylate - Names and Identifiers
| Name | Nequinate |
| Synonyms | Mequinate Nequinate Statoquate Methyl benzoquat methylbenzoquate nequinate Methylbenzoquate,Nequinate Statyl statil Statoquate Tranil methyl 7-(benzyloxy)-6-butyl-4-oxo-1,4-dihydroquinoline-3-carboxylate Methyl 7-(benzyloxy)-6-butyl-1,4-dihydro-4-oxo-3-quinolinecarboxylate 7-(Benzyloxy)-6-butyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid methyl ester 7-(Benzyloxy)-6-butyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid methyl ester 3-Quinolinecarboxylic acid, 7-(benzyloxy)-6-butyl-1,4-dihydro-4-oxo-, methyl ester 6-Butyl-1,4-Dihydro-4-Oxo-7-(Phenylmethoxy)-3-Quinolinecarboxylic Acid Methyl Ester 6-butyl-1,4-dihydro-4-oxo-7-(phenyl methoxy)-3-quinolinecarboxylic acid methyl ester 3-Quinolinecarboxylic acid, 6-butyl-1,4-dihydro-4-oxo-7-(phenylmethoxy)-, methyl ester |
| CAS | 13997-19-8 |
| EINECS | 237-796-6 |
| InChI | InChI=1/C22H23NO4/c1-3-4-10-16-11-17-19(23-13-18(21(17)24)22(25)26-2)12-20(16)27-14-15-8-6-5-7-9-15/h5-9,11-13H,3-4,10,14H2,1-2H3,(H,23,24) |
| InChIKey | NNOPDLNHPOLRRE-UHFFFAOYSA-N |
methyl 7-(benzyloxy)-6-butyl-4-oxo-1,4-dihydroquinoline-3-carboxylate - Physico-chemical Properties
| Molecular Formula | C22H23NO4 |
| Molar Mass | 365.42 |
| Density | 1.185±0.06 g/cm3(Predicted) |
| Melting Point | 287-288° |
| Boling Point | 520.7±50.0 °C(Predicted) |
| Flash Point | 268.7°C |
| Solubility | Acidic Methanol (Slightly, Heated, Sonicated) |
| Vapor Presure | 6.05E-11mmHg at 25°C |
| Appearance | neat |
| Color | White to Off-White |
| pKa | 1.06±0.70(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.579 |
| Physical and Chemical Properties | Light yellow or white crystalline powder, odorless, almost insoluble in water, ethanol, slightly soluble in chloroform, ether. FIG. 1 shows the chemical structural formula of benzylquinate. |
| Use | Coccidiostatic Drugs of Quinolines |
methyl 7-(benzyloxy)-6-butyl-4-oxo-1,4-dihydroquinoline-3-carboxylate - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| HS Code | 29334900 |
methyl 7-(benzyloxy)-6-butyl-4-oxo-1,4-dihydroquinoline-3-carboxylate - Reference Information
| application | quinoline anticoccidial drugs act on cystococcidial feres and schizonts of coccidia to inhibit the normal development of cystococcids and schizonts of the first generation. It is also reported that quinoline drugs play an anti-coccidial effect by inhibiting electron transfer in coccidia mitochondria. Many anticoccidial drugs, including methoxyquine, work by inhibiting the formation of cystic zygote, but the specific mechanism of this process is rarely reported. The mechanism of quinoline drugs against coccidia is that quinoline drugs can prevent the transport of mitochondrial electrons and have achieved the effect of inhibiting coccidia respiration, making coccidia unable to develop normally. The highest activity period of these compounds is the first day of the coccidia life cycle, that is, the child holding period, but they only play a role in inhibiting coccidia and cannot kill coccidia. |
| Broad-spectrum anti-coccidia drugs | Methoxyquine ester, also known as naphtoquinol ester, dicoquine ester, benzoxyquine methyl ester, Decoxyquinoline is a new type of quinoline broad-spectrum anti-coccidia drug, which is one of the stronger drugs. It plays a role in the asexual reproduction stage of coccidia. After entering the sporozoite cell, it prevents its development by interfering with DNA synthesis. It starts to play a role in the early life history of coccidia, thus avoiding damage to the intestinal tract of poultry. Except for the early-maturing Eimeria, the other 8 species of Eimeria have obvious anti-coccidia effect on the chicken, especially for the tender, toxic, giant, and heap Eimeria. The effect is significant, which is better than aminopyrine, chloropyridine, SQ and ballerin. This product 20 × 10-6~40 × 10-6 can completely control the infection of chicken coccidia, and the weight gain efficiency of the chickens is also significantly better than that of chloropyridine, dinitroamine, aminopyrine, butoxoquinoline and sulfaquinoxoline. It is a relatively new use in China and has no drug resistance. It is the most ideal rotation drug, and it can promote weight gain, improve coloring and other growth-promoting performance. Stable properties, under suitable temperature and humidity conditions, the product can maintain stable quality within 4 years. The European Union allows benzoxyquinyl methyl ester and chloropyridine to be mixed in a ratio of 8.35: 100, which has a synergistic effect. The mixture has high activity against tender and toxic Ehrlich, and is only 1/4 of the dose of chloropyridine alone. The metabolism is fast. After 3 days of drug withdrawal, the concentration of residual drugs in various tissues is lower than 1 × 10-6. It is the only chemical anticoccider approved by the governments of Japan, the European Union, the United States and China in the world. |
| preparation | preparation of A.3-(3-benzyloxy-4-butylanilinyl)-ethyl 2-cyanoacrylate (Ⅲ) is added to the reactor with 4-butyl-3-benzyloxyaniline (255g,1.0mol), 2-cyano-3-methoxyacrylate (186g,1.2mol), after stirring evenly, the temperature is raised to 30-35 ℃ for reaction, and the stirring reaction is continued for 8 hours. After the reaction is completed, the temperature is raised to 65 ℃ for distillation to remove the methanol generated by the reaction. The residue contains about 337.2g of 3-(3-benzyloxy-4-butyl aniline)-2-cyanoacrylate (Ⅲ), with a yield of about 89.2%, which can be directly used for the next reaction. Preparation of B .7-benzyloxy-6-butyl-4-cyano-3-cyanoquinoline (Ⅱ) Add 3-(3-benzyloxy-4-butylanilino)-2-Ethyl cyanoacrylate (Ⅲ)(378g,1.0mol), triethyl phosphate (3000g), after stirring evenly at room temperature, the temperature is raised to 120 ℃, and the stirring reaction is continued for 10 hours, after the reaction, cool to room temperature, first distill under normal pressure to remove the ethanol generated in the ring-closing reaction, and then distill under reduced pressure to remove the solvent triethyl phosphate, and the residue obtained is 7-benzyloxy-6-butyl-4-Cyano-3-cyanoquinoline (Ⅱ) crude product, recrystallized by ethanol to obtain 7-benzyloxy-6-butyl-4-cyano-3-cyanoquinoline (Ⅱ) boutique, it is 296.7g of off-white solid with a yield of about 89.4%. C. Preparation of trimethoxyquine (Ⅰ) Add 7-benzyloxy-6-butyl-4-cyano-3-cyanoquinoline (Ⅱ)(332g,1.0mol), methanol (3300g) and 15% hydrochloric acid (3300g) by weight in the reactor, stir evenly, heat to 45 ℃, stir for 5 hours, and then raise the temperature to reflux, continue to stir and react for 10 hours. After the reaction is finished, most of the solvent is removed by distillation, and the precipitated solid is filtered and collected. It is a crude product of trimethoprim (I). After recrystallization with methanol, trimethoprim (I) is obtained. The fine product is 312.5g of white or off-white solid, and the yield is about 85.6%,M.P.287.3-288.1 ℃. |
| Commonly used anti-coccidian agents | 1, naquine ester is also known as benzoxyquinyl methyl ester, benzoxyquinoline, trimethoxyquinoline, benzquinolate. It can prevent chicken poison, heap type, Brucella and other Eimeria coccidia, in quinolones anti coccidia effect is the best. 2. Aminopropylline hydrochloride is also known as Anbaoning and Aminopropyl pyridine. It has a significant effect on the soft and poisonous Ehrlich. It is the only anticoccidial drug that can be used in laying hens, and there is no requirement for withdrawal period. Use its two or three mixtures more. 3. Chloropyridine is also known as chloropyridine, dichlorodimethylpyridine, chloropyridine. The sporozoites of coccidia can remain undeveloped in epithelial cells or host macrophages for up to 60 days, which greatly exceeds the completion time of their normal reproductive cycle. If the drug is stopped during the period, the spores of the coccidiosis will develop again, so that the latent coccidiosis will attack again. It inhibits coccidia rather than kills coccidia. 4. Nicarbazine is also known as nitrourea pyrimidine and dinitrobenzenuril dimethylpyridol. It decomposes into monomers in the digestive tract of chickens and is absorbed by the intestines. Its absorption is faster, but its excretion is slower. It is mainly effective for Erydella soft, heaped Erydella, giant Erydella, toxic Erydella and Brucella. Its disadvantage is that when the amount is large, the chicken will be anorexic. When heavy-weight chickens use this drug under high temperature and high humidity conditions, the chickens will have reduced heat tolerance and a "heat stress response" will occur ". Some people think that nicarbazine has mutagenic and teratogenic effects. 5. Decaquine ester is also known as decaquine ester. It is effective against soft coccidia, giant coccidia, Brucella, toxic coccidia, heaped coccidia and variant coccidia. 6. Chlorphenanidine is also known as chlorphenanidine hydrochloride, robenidine, and diclofenidine. White crystalline powder. The biggest disadvantage of chlorobenzidine is that it has the peculiar odor of chloride. 7. Changshan ketone hydrobromide is also known as haloquinone, Changshan ketone, and Hailefu essence. It is less toxic, but toxic to ducks and geese. It has high coccidiocidal activity and is not easy to develop drug resistance. It is effective for chicken's soft Ehrlich, poisonous Ehrlich, translocated Ehrlich, heap Ehrlich, Brucella and giant Ehrlich. Toxic to fish and other aquatic animals. It is also irritating to the skin and eyes. |
| drug interaction | trimethoprim is combined with chloropyridine for synergy. |
| clinical application | is effective for 8 species of Eimeria coccidia. It is mainly used to prevent and control various coccidiosis in poultry (displacement, tenderness, giant, pile type, poison and Brinell, etc.). |
| usage and dosage | mixed feeding: 20-30 mg of poultry per kilogram of feed. |
| precautions | ① trimethoxazole has low toxicity, good tolerance, and is still safe to use 80 times the recommended amount. ② It is forbidden to start giving birth to backup hens and laying hens. ③ this product can inhibit the body's immunity to coccidia, and broilers should be used continuously during the whole growth process. ④ cannot be used in feed containing bentonite. The powder of this product should be about 1.8 microns in order to exert the anti-coccidia effect. |
| use | as a feed additive. |
Last Update：2024-04-09 18:58:34
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