1-乙基-6,7-亚甲氧基-4-喹啉酮-3-羧酸
Oxolinic Acid
CAS: 14698-29-4
Molecular Formula: C13H11NO5
1-乙基-6,7-亚甲氧基-4-喹啉酮-3-羧酸 - Names and Identifiers
1-乙基-6,7-亚甲氧基-4-喹啉酮-3-羧酸 - Physico-chemical Properties
| Molecular Formula | C13H11NO5 |
| Molar Mass | 261.23 |
| Density | 1.3038 (rough estimate) |
| Melting Point | 314-316°C (dec.) |
| Boling Point | 473℃ |
| Flash Point | >110°(230°F) |
| Water Solubility | 3.214mg/L(temperature not stated) |
| Solubility | Almost insoluble in water and ethanol, soluble in acetic acid and sodium hydroxide solution. |
| Vapor Presure | 9.24E-10mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | White |
| Merck | 13,7014 |
| BRN | 620635 |
| pKa | 5.94±0.20(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable. Combustible. |
| Sensitive | Light Sensitive |
| Refractive Index | 1.5500 (estimate) |
| MDL | MFCD00056775 |
| Physical and Chemical Properties | This product is solid. m. P. 310 °c, relative density 1.55 (25 °c), vapor pressure <1.46 x 10-4Pa (100 °c). 25 degrees in acetone, ethyl acetate, methanol solubility <1.0%, water solubility 0.003mg/L. It can react with sodium hydroxide to form salt, and its salt is soluble in water. Stable to heat, humidity and light. |
| Use | Quinolinone fungicides, used in rice seed treatment, known as the refractory disease of rice disease disease of the Valley blight (seedling rot disease) with excellent effect of the first fungicides. Before sowing, the seed dressing treatment can inhibit the occurrence of the disease caused by the disease of the grain blight bacteria, and the occurrence of the disease can be prevented after transplanting the robust seedling to the red, and then the occurrence of the disease can be prevented. The mechanism of action is that it has a wide range of antibacterial activity against Gram-negative work, but it has weak activity against Gram-positive bacteria and no activity against fungi. By inhibiting the synthesis of DNA, it hinders the division and proliferation of bacteria. In the bacterial cell, the super coil structure of DNA is introduced into the reverse Super coil enzyme, and the agent can be combined with the subgroup A of this enzyme, as a result, its function is suppressed and DNA cannot be replicated, and death is caused soon. Soaking seeds at 1000g/mL for 24h,10 |
1-乙基-6,7-亚甲氧基-4-喹啉酮-3-羧酸 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S60 - This material and its container must be disposed of as hazardous waste. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | JI5075000 |
| FLUKA BRAND F CODES | 10 |
| HS Code | 29349990 |
| Toxicity | LD50 in mice, rats (mg/kg): >6000, >2000 orally (Turner) |
1-乙基-6,7-亚甲氧基-4-喹啉酮-3-羧酸 - Reference
| Reference Show more | 1. [IF=7.514] Bolong Fang et al."Glucose oxidase-induced colorimetric immunoassay for qualitative detection of danofloxacin based on iron (Ⅱ) chelation reaction with phenanthroline."Food Chem. 2020 Oct;328:127099 2. [IF=2.082] Qin Guo et al."Synergistic inhibition effects of tea polyphenols as adjuvant of oxytetracycline on Vibrio parahaemolyticus and enhancement of Vibriosis resistance of Exopalaemon carinicauda."Aquac Res. 2021 Aug;52(8):3900-3910 |
1-乙基-6,7-亚甲氧基-4-喹啉酮-3-羧酸 - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| quinolinone fungicides | oxoquinolinic acid, also known as oxoquinolinic acid, oxolinic acid, orinic acid, belongs to the second generation of quinolinone fungicides. It is white with yellow and white columnar crystals or crystalline powder at room temperature. It is odorless and tasteless. It has strong antibacterial effect against Gram-negative bacteria and some positive bacteria, and has no cross-resistance with antibiotics, however, it has no antibacterial effect on fungi and Mycobacterium tuberculosis. It has the advantages of low dosage and good antibacterial effect. It is mainly used to treat bacterial diseases of fish and shrimp. Aquaculture farmers believe that it is one of the ideal drugs for the treatment of aquatic animal diseases. It has quite strong antibacterial activity against fish pathogens such as Vibrio anguillarum and Aeromonas hydrophila. Therefore, eels and other aquatic animals in Japan and Taiwan Province are widely used. PH has a slight impact on them in mariculture, and the dosage should be increased in alkaline environment. Oxolinic acid has little toxicity, acute, toxicity test for carp oral median lethal dose (that is, under the influence of a certain concentration of the drug can make 50% individual death time) is more than 4000 mg/kg. The use of this drug must be stopped 25 days ago, otherwise the residual amount exceeds the standard. The Japanese market prohibits imports. Taiwan has updated the allowable amount of Oxolinic acid in the muscle, fat, liver and kidney of fish, shrimp, eggs, cattle, pigs, and chickens. There is an evolutionary process in the use of eel drugs in various countries. In September 1991, Japan's International Bureau of Veterinary Epidemic Affairs held a special meeting to discuss the use standards of aquatic medicine for Japanese eels and the issue of chemotherapy in aquaculture, involving therapies, drug toxicity, drug resistance, residues and other issues. The general trend is: fish diseases increase and therapeutic drugs increase, the increase of residual drugs in the environment is a new and important problem facing the breeding interface. Therefore, Japan revised the use standard of aquatic medicines three times from 1991 to 1992, and promulgated the "standard" for the use of eel aquatic medicines. The names and methods of use of drugs that can be used and those that cannot be used. Although oxolinic acid is listed as a drug that can be used within the scope of the use standard, and the oxolinic acid has a withdrawal period of 25 days, less than 20 mg/kg of fish/day, and the oral and pharmaceutical solvent is maintained for 6 hours, the China Food, Native Animal Import and Export Chamber of Commerce In order to make my country's export eel breeding scientific, its products meet the food hygiene requirements of the importing country, enhance the confidence of importers in purchasing Chinese eels, and stabilize the export market, on April 28, 1989, it issued a document promulgating the health management and medication management (interim) measures for China's export eel. It is clearly stipulated that oxolinic acid and malachite green methyl blue are prohibited drugs. |
| toxicity | the original drug has acute oral LD50630mg/kg (male) and 570 mg/kg (female) on rats. Acute oral LD502200mg/kg for male mice and 1450 mg/kg for female mice; Acute percutaneous LD50>2000 mg/kg in rats has no irritating effect on skin and mild irritating effect on eyes. No sensitization. The non-effective dose of rats fed for 2 years was 100~300 mg/kg. Animal experiments have no teratogenic, carcinogenic or mutagenic effects. According to the conventional method, it has no effect on fish, carp LC5010mg/L (48h). |
| Uses | Quinolinone fungicides, used for rice seed treatment, are called the first fungicide with outstanding effect on rice refractory disease (seedling corruption). Seed dressing with a medicament before sowing can inhibit the occurrence of bacterial disease caused by grain blight. After transplanting the robust seedlings to Honda, the occurrence of bacterial disease can be prevented. The mechanism of action is that it has a wide range of antibacterial activity against Gram-negative work, but its activity against Gram-positive bacteria is weak and has no activity against fungi. By inhibiting the synthesis of DNA, the division and proliferation of the bacteria are hindered. In the bacteria, the super-coiled structure of DNA is introduced into the reverse super-coiled enzyme. This agent can bind to subgroup A of this enzyme, so that its function is suppressed and the DNA cannot be replicated, which will soon cause death. Soaking seeds with 1000 g/mL for 24h,1000 g/mL for 10min, or 20% wettable powder for seed coating with seed quality 0.5%, the control effect reached more than 97%. This product can also be used to control rice grain rot, potato black cavity disease, soft rot, fire blight and similar diseases. If 300~600g active ingredient/hm2 foliar spraying at the heading stage of rice, rice grain rot can be controlled. Spraying 300~600g active ingredient/hm2 foliar can prevent fire blight and soft rot of apples and pears. It also has a good protective and therapeutic effect on cabbage soft rot. It is used to treat bacterial diseases of fish, shrimp and other aquatic animals. It has a good therapeutic effect on furuncle disease, Vibrio disease, nodule disease, red fin disease, red spot disease, ulcer disease, enteritis disease, etc. It has a strong broad-spectrum, has a strong antibacterial effect on Gram-negative bacteria and some positive bacteria, and has no cross-drug with antibiotics, but has no antibacterial effect on fungi and Mycobacterium tuberculosis, and has low dosage, Good antibacterial effect and other advantages, aquaculture farmers think he is one of the ideal drugs for the treatment of aquatic animal diseases. It has considerable antibacterial activity against fish pathogens such as Vibrio anguillarum and Aeromonas hydrophila. |
| Production method | Preparation of methylenedioxyaniline Methylenedioxyaniline is prepared by nitration and reduction of methylenedioxybenzene. Synthesis of quinone Methylenedioxyaniline and diethyl ethoxy methylene malonic acid are heated and reacted at 80~90 ℃ for 3h, then refluxed and cyclized in xylene, then N-alkylation reaction is carried out with iodide ethane in DMF solvent at 70~75 ℃ in the presence of sodium hydroxide, the mixture is diluted with water and refluxed for 3~4h, and the hydrolysate is acidified with hydrochloric acid to generate quinone. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:10
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