阅读说明：本技术 N-（2-溴-4-氟苯基）-2-（2-氯-4-氟苯氧基）乙酰胺及其用途 (N- (2-bromo-4-fluorophenyl) -2- (2-chloro-4-fluorophenoxy) acetamide and application thereof ) 是由 杜春华 刘胜芬 许洁 王菊 白玉兰 于 2020-06-17 设计创作，主要内容包括：公开了一种化合物N-(2-溴-4-氟苯基)-2-(2-氯-4-氟苯氧基)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-氯-4-氟苯酚、碳酸钾、乙腈、碘化钾,低温下滴加N-(2-溴-4-氟苯基)-2-氯乙酰胺的乙腈液,然后将反应液升温至回流继续反应,反应结束后,从滤液获取产物。该化合物对杂草种子和植物病原菌具有较高的抑制作用。(Discloses a compound N- (2-bromo-4-fluorophenyl) -2- (2-chloro-4-fluorophenoxy) acetamide, a preparation method and agricultural biological activity thereof. The preparation method comprises the steps of adding 2-chloro-4-fluorophenol, potassium carbonate, acetonitrile and potassium iodide into a reactor, dropwise adding acetonitrile liquid of N- (2-bromo-4-fluorophenyl) -2-chloroacetamide at low temperature, heating the reaction liquid to reflux for continuous reaction, and obtaining a product from the filtrate after the reaction is finished. The compound has high inhibition effect on weed seeds and plant pathogenic bacteria.)

1. A compound which: n- (2-bromo-4-fluorophenyl) -2- (2-chloro-4-fluorophenoxy) acetamide having the following structure:

。

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

the preparation method comprises the steps of adding 2-chloro-4-fluorophenol, potassium carbonate, acetonitrile and potassium iodide into a nitrogen replacement reactor, dropwise adding acetonitrile liquid of N- (2-bromo-4-fluorophenyl) -2-chloroacetamide at low temperature, heating the reaction liquid to reflux for continuous reaction, filtering after the reaction is finished, and concentrating the filtrate to obtain the product.

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

4. Use of a compound according to claim 1 for controlling weeds.

Technical Field

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

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-bromo-4-fluorophenyl) -2- (2-chloro-4-fluorophenoxy) acetamide is found to have high-efficiency herbicidal and bactericidal activity.

Disclosure of Invention

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

The scheme of the invention is as follows:

n- (2-bromo-4-fluorophenyl) -2- (2-chloro-4-fluorophenoxy) acetamide may be prepared by the following route:

the preparation method comprises the steps of adding 2-chloro-4-fluorophenol, potassium carbonate, acetic anhydride, acetonitrile and potassium iodide into a reactor, dropwise adding acetonitrile liquid of N- (2-bromo-4-fluorophenyl) -2-chloroacetamide at the temperature of 20-60 ℃, heating the reaction liquid to reflux for continuous reaction, filtering after the reaction is finished, and concentrating the filtrate to obtain the product.

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

The compound of the invention has high-efficiency bactericidal and herbicidal activity.

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

Example 1: 8.1 g of 2-chloro-4-fluorophenol, 13.8g of potassium carbonate, 120mL of acetonitrile and 0.75g of potassium iodide were added to a dry reaction flask replaced with nitrogen, and the mixture was stirred at 40 ℃ for 20 minutes, and a mixture of 13.3 g N- (2-bromo-4-fluorophenyl) -2-chloroacetamide and 15mL of acetonitrile was added dropwise over 2 hours, and the mixture was heated and reacted under reflux for about 20 hours. After the reaction is finished, filtering and concentrating to obtain a crude product N- (2-bromo-4-fluorophenyl) -2- (2-chloro-4-fluorophenoxy) acetamide, and recrystallizing to obtain 7.8g of a light yellow product.