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Triazine compound and application thereof in chicken coccidiosis disease control
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A triazine compound and the technology of the compound are applied to the triazine compound and its application field in controlling chicken coccidiosis, and can solve the problems of increasing the difficulty of preparation preparation, high concentration of use, and easy generation of drug resistance, etc. Good preventive and therapeutic effects
Active Publication Date: 2013-07-03
SHANGHAI VETERINARY RES INST CHINESE ACAD OF AGRI SCI
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In terms of application, diclazuril is mainly used for the prevention of coccidiosis; it can also be used for treatment, but it is easy to produce drug resistance; In the treatment of coccidiosis, it is also prone to drug resistance
[0008] In terms of physical and chemical properties, diclazuril is almost insoluble in common solvents such as water and ethanol (edited by the Chinese Veterinary Pharmacopoeia Committee, the 2005 edition of the Veterinary Pharmacopoeia of the People's Republic of China, China Agricultural Press, 2006:68; Yao Weimin et al., Dike Research and development of Zhuli drinking water agent, Animal and Poultry Industry, 1999, 4:21-22; Ouyang Yan et al., Research and quality inspection of diclazuril nanoemulsion, Heilongjiang Animal Husbandry and Veterinary Medicine, 2007, 11:92-93); Toltrazuril is also almost insoluble in most solvents such as ethanol; the characteristics of these triazine compounds greatly increase the difficulty of preparation preparation and the inconvenience during use
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Embodiment 1
[0033] 2-{3-methyl-4-(4'-nitrophenoxy)phenyl}-1,2,4-triazine-3,5(2H,4H)-dione (compound of formula (I) ) preparation
[0034] Add compound Ⅱ (15 grams, 0.068mol), anhydroussodiumcarbonate (7.9 grams, 0.075mol), p-chloronitrobenzene (11.8 grams, 0.075mol) and DMF (150ml) into a four-neck flask and heat to 120°C After reacting for 10 hours, after cooling down to room temperature, the reaction solution was poured into 1000ml of water, adjusted to pH=3 with 10% dilute hydrochloric acid, and a pale yellow solid was precipitated, filtered, washed with water, and dried to obtain the compound of formula (I) (16.2 g, 69.5%)
[0037] 2-{3-methyl-4-(4'-nitrophenoxy)phenyl}-1,2,4-triazine-3,5(2H,4H)-dione (compound of formula (I) ) preparation
[0038] Compound II (15 g, 0.068 mol), anhydrouspotassiumcarbonate (10.4 g, 0.075 mol), p-chloronitrobenzene (11.8 g, 0.075 mol) and DMSO (100 ml), were added to a four-necked flask and heated to 130°C After reacting for 8 hours, after cooling down to room temperature, the reaction solution was poured into 1000ml of water, adjusted to pH=3 with 10% dilute sulfuric acid, and a pale yellow solid was precipitated, filtered, washed with water, and dried to obtain the compound of formula (I) (15 g, 64.3%).
Embodiment 3
[0040] Preparation of 2-(3-methyl-4-hydroxyphenyl)-1,2,4-triazine-3,5(2H,4H)-diketonol sodium salt
[0041] Compound Ⅱ (150 g, 0.68 mol), 500 g toluene, heated to dissolve, 30% sodium methoxide solution was added dropwise, a yellow powder was precipitated, filtered, washed with methanol, and dried to obtain 2-(3-methyl-4-hydroxybenzene base)-1,2,4-triazine-3,5(2H,4H)-diketonesodium salt (147.5 g, 90%).
[0042] ESI-MS (m / z): 218.1(M-Na) - .
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Abstract
Disclosed are a compound of Formula (I) and use thereof in control of chicken coccidiosis. The compound of Formula (I) is prepared from a compound of Formula (II) or a phenolic sodium salt thereof and a compound of Formula (III) through condensation at a basic condition, wherein in the compound of Formula (III), the substituent x is a halogen. The compound of Formula (I) according to the present invention functions in both prevention and treatment of chicken coccidiosis, with desirable activity against chicken coccidia at a concentration of 0.5 to 20 mg / kg.
Description
technical field [0001] The present invention relates to compound and the application of compound, especially a kind of new triazine compound and its application in controlling chicken coccidiosis, and the synthesis method of the compound. Background technique [0002] Chicken coccidiosis is an intracellularparasitic disease mainly caused by intestinal lesions caused by one or several Eimeria chickens. It is a highly contagious parasitic disease that can cause chicken growth rate and The reduction of feed conversion rate and the decline of meat and egg quality. In severe cases, it can cause death of chickens. According to statistics, the incidence of coccidiosis in chickens is 50-70%, and the outbreakmortality rate reaches 20-30%. The economic loss caused by chicken coccidiosis in the world reaches 5 billion US dollars every year. my country is a big chicken raising country, accounting for 10% of the world's total chicken raising, and the direct and indirect economic loss...
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