A kind of triazine compound and its application in controlling chicken coccidiosis

Abstract

The invention discloses a compound represented by a formula (I) and application thereof to chicken coccidiosis disease control. The compound represented by the formula (I) is obtained by condensation of a compound represented by a formula (II) or sodium phenolate thereof with a compound represented by a formula (III) under the alkaline condition, wherein a substituent group x in the compound represented by the formula (III) is halogen. The compound represented by the formula (I) has the effects of preventing and treating a chicken coccidiosis disease, and has good chicken coccidiosis resisting activity when in concentration of 0.5-20mg / 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 intracellular parasitic 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 outbreak mortality 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...

Examples

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), anhydrous sodium carbonate (7.9 grams, 0.075mol), p-chloronitrobenzene (11.8 grams, 0.075mol) and DMF (150ml) into a four-necked 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%)

[0035] mp: 169 – 171.5°C. ESI-MS (m / z): 339.2(M-H) - , 1HNMR (CDCl 3): 2.25 (s, 3H), 7.00 (d, 2H), 7.09 (d, 1H), 7.44(d,1H), 7.50(s,1H), 7.60(s,1H), 8.22(d,2H) , 9.69 (s, 1H).

Embodiment 2

[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), anhydrous potassium carbonate (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)-diketone sodium salt (147.5 g, 90%).

[0042] ESI-MS (m / z): 218.1(M-Na) - .

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 intracellular parasitic 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 outbreak mortality 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...

Examples

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), anhydrous sodium carbonate (7.9 grams, 0.075mol), p-chloronitrobenzene (11.8 grams, 0.075mol) and DMF (150ml) into a four-necked 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%)

[0035] mp: 169 – 171.5°C. ESI-MS (m / z): 339.2(M-H) - , 1HNMR (CDCl 3): 2.25 (s, 3H), 7.00 (d, 2H), 7.09 (d, 1H), 7.44(d,1H), 7.50(s,1H), 7.60(s,1H), 8.22(d,2H) , 9.69 (s, 1H).

Embodiment 2

[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), anhydrous potassium carbonate (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)-diketone sodium salt (147.5 g, 90%).

[0042] ESI-MS (m / z): 218.1(M-Na) - .

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