阅读说明：本技术 N-（2-氯-4-氟苯基）-2-（2,4,6-三氯苯氧基）乙酰胺及其用途 (N- (2-chloro-4-fluorophenyl) -2- (2, 4, 6-trichlorophenoxy) acetamide and application thereof ) 是由 杜春华 刘胜芬 王菊 吴现力 康武魁 于 2020-06-17 设计创作，主要内容包括：公开了一种化合物N-(2-氯-4-氟苯基)-2-(2,4,6-三氯苯氧基)乙酰胺及其制备方法和农用生物活性。制备方法是在反应器内加入2,4,6-三氯苯酚、碳酸钾、DMF、碘化钾,在60-80℃下滴加N-(2-氯-4-氟苯基)-2-氯乙酰胺的DMF液,将反应液升温到100℃继续反应,反应结束后,过滤,从滤液获得产物。该化合物对植物病原菌具有广谱的抑制作用。(A compound N- (2-chloro-4-fluorophenyl) -2- (2, 4, 6-trichlorophenoxy) acetamide, its preparing process and its agricultural bioactivity are disclosed. The preparation method comprises the steps of adding 2,4, 6-trichlorophenol, potassium carbonate, DMF and potassium iodide into a reactor, dropwise adding DMF solution of N- (2-chloro-4-fluorophenyl) -2-chloroacetamide at the temperature of 60-80 ℃, heating the reaction solution to 100 ℃ for continuous reaction, and filtering after the reaction is finished to obtain the product from the filtrate. The compound has broad-spectrum inhibitory effect on plant pathogenic bacteria.)

1. A compound which: n- (2-chloro-4-fluorophenyl) -2- (2, 4, 6-trichlorophenoxy) acetamide, which has the following structure:

2. the compound of claim 1 is prepared by the following route:

the preparation method comprises the steps of adding 2,4, 6-trichlorophenol, potassium carbonate, DMF and potassium iodide into a nitrogen replacement reactor, dropwise adding DMF solution of N- (2-chloro-4-fluorophenyl) -2-chloroacetamide at the temperature of 60-80 ℃, heating the reaction solution to 100 ℃ for continuous reaction, filtering after the reaction is finished, and obtaining a product from the filtrate.

3. Use of the compound of claim 1 for controlling plant diseases.

Technical Field

The invention relates to a compound N- (2-chloro-4-fluorophenyl) -2- (2, 4, 6-trichlorophenoxy) acetamide, a preparation method thereof and agricultural biological activity, and particularly relates to the fields of organic compounds, organic synthesis and agricultural sterilization.

Background

The pesticide plays a significant role in preventing and controlling pests in agriculture and forestry. At present, it can be said that there is no safety of plants without pesticides. With the development of resistance, the market is in urgent need for new pesticides, especially for new mechanisms of action. Because fluorine atoms have large electronegativity and small radius, the formed C-F bond energy is much larger than that of a C-H bond, so that the organic fluorine compound has good stability, and after a fluorine-containing group is introduced into an active compound, complex physiological activity is generated due to the synergistic effect of an electronic effect, a blocking effect, a pseudo effect and a permeation effect of a fluorine-containing substituent. The creation of fluorine-containing drugs has become an important direction for the development of new medicines and new pesticides. Based on this, we studied the synthesis and creation methods of fluorine-containing physiologically active compounds. Through synthesis and activity screening for many years, the compound N- (2-chloro-4-fluorophenyl) -2- (2, 4, 6-trichlorophenoxy) acetamide is found to have high-efficiency broad-spectrum bactericidal activity.

Disclosure of Invention

The invention aims to provide a compound N- (2-chloro-4-fluorophenyl) -2- (2, 4, 6-trichlorophenoxy) acetamide and a preparation method and application thereof.

The scheme of the invention is as follows:

n- (2-chloro-4-fluorophenyl) -2- (2, 4, 6-trichlorophenoxy) acetamide may be prepared by the following route:

the preparation method comprises the steps of adding 2,4, 6-trichlorophenol, potassium carbonate, DMF and potassium iodide into a reactor, dropwise adding DMF solution of N- (2-chloro-4-fluorophenyl) -2-chloroacetamide at the temperature of 60-80 ℃, heating the reaction solution to 100 ℃ for continuous reaction, filtering after the reaction is finished, and obtaining a product from the filtrate.

The synthesis method of the invention has the following characteristics: less reaction steps, good selectivity, cheap and easily obtained raw materials, simple operation and stable process.

The compound of the invention has high bactericidal activity.

The following examples are intended to further illustrate the invention but are not to be construed as limiting the invention thereto.

Example 1: in a dry nitrogen-substituted reaction flask, 3.2 g of 2,4, 6-trichlorophenol, 4.2 g of potassium carbonate, 30mL of DMF and 0.25g of potassium iodide are added, the mixture is heated to 60 ℃ and stirred for reaction for 20 min, a mixed solution of 3.3g of N- (2-chloro-4-fluorophenyl) -2-chloroacetamide and 10mL of DMF is uniformly added dropwise within 2 hours, and the temperature is raised to 100 ℃ for reaction for about 20 h. After the reaction is finished, the crude product N- (2-chloro-4-fluorophenyl) -2- (2, 4, 6-trichlorophenoxy) acetamide is obtained by filtering and vacuum concentration, and light yellow solid 2.25 g is obtained by silica gel column chromatography.