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Synthesis method of bisamide insecticide

A synthesis method and bisamide technology are applied in the directions of biocides, biocides, botanical equipment and methods, etc., which can solve the problems of cumbersome reaction steps, low product yield, and many side reactions, and achieve high purity and yield. Good and pollution-reducing effect

Active Publication Date: 2021-10-26
SHANDONG ACADEMY OF PESTICIDE SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] For this reason, the present invention provides a kind of synthesis method of bisamide insecticides, to solve the existing synthesis method of bisamide insecticides with complex reaction steps, many side reactions, low product yield, easy to produce acidic acids such as hydrogen chloride, etc. Gas will corrode equipment and other problems

Method used

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  • Synthesis method of bisamide insecticide
  • Synthesis method of bisamide insecticide
  • Synthesis method of bisamide insecticide

Examples

Experimental program
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Effect test

Embodiment 1

[0039] A kind of synthetic method of bisamide insecticide, described reaction formula is specifically as follows:

[0040]

[0041] The specific steps of the synthetic method are as follows:

[0042] To a 100mL reaction flask, add 3-bromo-1-(3,5-dichloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid (3.57g, 95%, 10 mmol) and acetonitrile (15 mL), the mixture was cooled to -5 °C, and then methanesulfonyl chloride (2.78 g, 99%, 24 mmol) was added dropwise to the reaction flask at -5 °C to 0 °C. After the dropwise addition was completed, stir at room temperature for 10 min, then slowly heat to 50° C., and keep warm for 10 h to obtain a reaction mixture.

[0043] The resulting reaction mixture was cooled to 25°C, 2-amino-3,5-dichlorobenzamide (2.40g, 97%, 10.5mmol) and pyridine (2.24g, 99%, 28mmol) were added, and at this temperature After stirring at low temperature for 3 h, water (5 mL) was added dropwise, and the mixture was stirred at room temperature for 1 h to ob...

Embodiment 2

[0053] To a 100mL reaction flask, add 3-bromo-1-(3,5-dichloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid (3.57g, 95%, 10 mmol) and toluene (15 mL), the mixture was cooled to -5 °C, and then methanesulfonyl chloride (2.78 g, 99%, 24 mmol) was added dropwise to the reaction flask at -5 °C to 0 °C. After the dropwise addition was completed, stir at room temperature for 10 min, then slowly heat to 50° C., and keep warm for 10 h to obtain a reaction mixture.

[0054] The resulting reaction mixture was cooled to 25°C, 2-amino-3,5-dichlorobenzamide (2.40g, 97%, 10.5mmol) and pyridine (2.24g, 99%, 28mmol) were added, and at this temperature After stirring at low temperature for 3 h, water (5 mL) was added dropwise, and the mixture was stirred at room temperature for 1 h to obtain the crude product.

[0055] The crude product was filtered, and the solid was washed with 3:1 toluene-water (2×3 mL) and then with toluene (3 mL), and the solid was filtered and dried to obtain the...

Embodiment 3

[0059] To a 100mL reaction flask, add 3-bromo-1-(3,5-dichloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid (3.57g, 95%, 10 mmol) and acetonitrile (15 mL), the mixture was cooled to -5 °C, and then methanesulfonyl chloride (2.78 g, 99%, 24 mmol) was added dropwise to the reaction flask at -5 °C to 0 °C. After the dropwise addition was completed, stir at room temperature for 10 min, then slowly heat to 50° C., and keep warm for 10 h to obtain a reaction mixture.

[0060] The resulting reaction mixture was cooled to 25°C, and 2-amino-3,5-dichlorobenzamide (2.40g, 97%, 10.5mmol) and triethylamine (2.86g, 99%, 28mmol) were added. After stirring at this temperature for 3 h, water (5 mL) was added dropwise, and the mixture was stirred at room temperature for 1 h to obtain a crude product.

[0061] The crude product was filtered, and the solid was washed with 3:1 acetonitrile-water (2×3 mL) and then with acetonitrile (3 mL), the solid was filtered and dried to obtain a bisami...

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Abstract

The invention discloses a synthesis method of a bisamide insecticide, which relates to the technical field of organic synthesis. The synthesis method comprises the steps that a pyrazoline carboxylic acid compound shown in the general formula (III) and an anthranilamide compound shown in the general formula (II) serve as raw materials; methanesulfonyl chloride is used as an oxidizing agent and a condensing agent to synthesize the bisamide insecticide as shown in the general formula (I) in one step. According to the synthesis method, a pyrazoline carboxylic acid compound and an anthranilamide compound are used as raw materials, methylsulfonyl chloride is used as an oxidizing agent and a condensing agent, a coupling reaction and an oxidation reaction are carried out at the same time under the action of certain tertiary amine, in the coupling reaction process, pyrazoline can be epoxidized into a pyrazole ring at the same time, the bisamide insecticide with high purity and high yield is prepared by adopting the method, the traditional oxidation reaction carried out by adopting an oxidizing agent is successfully replaced, the reaction steps are simplified, the pollution to the environment is reduced, and the reaction safety is improved.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing bisamide insecticides. Background technique [0002] Bisamide insecticides are a hot topic in the field of insecticide research in recent years. They act on the ryanodine receptors of insects. They have a novel mechanism of action, high efficiency, no cross-resistance with traditional pesticides, and are harmful to non-target biological safety and the environment. Good compatibility and other characteristics have attracted people's attention and become a hot spot in the research and development of insecticides. [0003] The well-known bisamide insecticides in the existing market include chlorantraniliprole developed by DuPont and tetrachlorantraniliprole developed by Shenyang Research Institute of Chemical Industry Co., Ltd. [0004] Chlorantraniliprole, developed by DuPont, first uses potassium persulfate and concentrated sulfuric acid as oxi...

Claims

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Application Information

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IPC IPC(8): C07D401/04A01N43/80A01P7/00
CPCC07D401/04A01N43/80Y02A50/30
Inventor 丛云波韩金涛蒋爱忠刘军解银萍王滢秀郝泽生江忠萍
Owner SHANDONG ACADEMY OF PESTICIDE SCI
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