Synthetic method of emamectin benzoate crude product

A synthetic method, the technology of emamectin benzoate, which is applied in the direction of chemical instruments and methods, organic chemistry, sugar derivatives, etc., can solve the problems of high consumption, high production cost and high price of emamectin benzoate, and achieve simplified synthesis process steps, The advantages of production cost are obvious, and the effect of being easy to recycle and reuse

Active Publication Date: 2019-12-13
NINGXIA TAIYICIN BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007]1 takes avermectin as the initial raw material, and obtains formazan through synthetic steps such as hydroxyl protection, oxidation, ammoniation, hydrogenation reduction, deprotection reaction and salt-forming reaction. Crude vitamin salt, the synthetic route is more complicated
[0008]2 A variety of raw materials are involved in the synthesis of emamectin emamectin salt. Due to the high price and high consumption, the production cost of emamectin emamectin salt is high and the economic benefit is high. Low
[0009]3 This production process uses many kinds of organic reagents, a

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Abamectin B1a lkg (1.14mol), dissolved in 10L dimethylformamide.

[0048] Oxidation reaction: first add 0.02 kg of silver carbonate catalyst, then add 0.6 L of 5% dilute hydrochloric acid solution, stir for 5 min, and add 0.2 kg of oxidant di-tert-butyl peroxide at a solution temperature of 0°C, and react for 40 min. After the reaction, add 0.4L of 10% sodium bicarbonate solution and 40ml of 40% sodium sulfite solution, stir for 20min, filter to obtain a compound A solution, concentrate and dry under reduced pressure to obtain 0.953kg of solid compound A, then add 9.5L of purified water, wash with water Once and dried, 0.951 kg (1.09 mol) of solid compound A was obtained, and the yield was 95.1%.

[0049]Amination reaction: Dissolve the solid compound A obtained from the oxidation reaction and 0.23kg (1.31mol) of heptamethyldisilazane in 10L of reaction solvent dimethylformamide, control the solution temperature at 20°C, and add 0.006kg of sodium methoxide ( 0.11mol), ...

Embodiment 2

[0053] Abamectin B1a lkg (1.14mol), dissolved in 11L dimethylformamide.

[0054] Oxidation reaction: first add 0.04 kg of silver carbonate catalyst, then add 0.9 L of 7.5% dilute hydrochloric acid solution, stir for 10 min, and add 0.23 kg of oxidant di-tert-butyl peroxide at a solution temperature of 3°C, and react for 50 min. After the reaction, add 0.6L of 15% sodium bicarbonate solution and 58ml of 45% sodium sulfite solution, stir for 30min, filter to obtain a compound A solution, concentrate and dry under reduced pressure to obtain 0.964kg of solid compound A, then add 14.5L of purified water, wash with water Once and dried, 0.962 kg (1.10 mol) of solid compound A was obtained, and the yield was 95.7%.

[0055] Amination reaction: Dissolve the solid compound A obtained from the oxidation reaction and 0.30kg (1.54mol) of heptamethyldisilazane in 11L of reaction solvent dimethylformamide, control the solution temperature at 25°C, and add 0.009kg of sodium methoxide ( 0.16...

Embodiment 3

[0059] Abamectin B1a lkg (1.14mol), dissolved in 12L dimethylformamide.

[0060] Oxidation reaction: firstly add 0.06kg of catalyst silver carbonate, then add 1.2L of 10% dilute hydrochloric acid solution, stir for 15min, and add 0.27kg of oxidant di-tert-butyl peroxide at a solution temperature of 5°C, and react for 60min. After the reaction, add 0.8L of 20% sodium bicarbonate solution and 81ml of 50% sodium sulfite solution, stir for 40min, filter to obtain a compound A solution, concentrate and dry under reduced pressure to obtain 0.953kg of solid compound A, then add 19L of purified water, wash with water for 1 and dried to obtain 0.948kg (1.09mol) of solid compound A with a yield of 94.8%.

[0061] Amination reaction: Dissolve the solid compound A obtained from the oxidation reaction and 0.305kg (1.744mol) of heptamethyldisilazane in 12L of reaction solvent dimethylformamide, control the temperature of the solution at 30°C, and add 0.012kg of sodium methoxide ( 0.22mol),...

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PUM

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Abstract

The invention relates to a synthetic method of an emamectin benzoate crude product, which is characterized in that: avermectin B1a is used as an initial raw material, and is subjected to an oxidationreaction, an ammoniation reaction, a reduction reaction and a salification reaction to obtain the emamectin benzoate crude product, and the reactions are carried out in a reaction system using dimethylformamide, tetrahydrofuran or tetrahydropyrane as a reaction solvent. According to the invention, the abamectin B1a is directly used as an initial synthesis raw material; the emamectin benzoate is synthesized by adopting a four-step method instead of a six-step method, so that the synthesis process steps are simplified, the production period is shortened, the production cost advantage is obvious,only one reaction solvent is used in the whole synthesis process, the recycling is convenient, the discharge amount of byproducts is very low, and the environmental pollution is not easily caused.

Description

technical field [0001] The invention belongs to the technical field of antibiotic synthesis, in particular to a method for synthesizing crude emamectin emamectin by using abamectin B1a. Background technique [0002] Emamectin benzoate, also known as emamectin benzoate, is a high-efficiency, low-toxicity, low-residue, green and environment-friendly biological source insecticide developed and marketed by Novartis. Emamectin benzoate is a derivative of abamectin, a biological fermentation product, and its biological activity is higher than that of abamectin compared with the parent. Emamectin emamectin has a wide insecticidal spectrum, and has a good poisonous effect on cotton bollworm, beet armyworm, gray winged armyworm, tobacco armyworm, etc., especially for Lepidoptera pests, the insecticidal effect is excellent, It is widely used in cabbage, cabbage and other vegetables, soybeans, tobacco, rice and other crops and fruit trees. Therefore, the unique insecticidal mode of e...

Claims

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Application Information

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IPC IPC(8): C07H17/08C07H1/00
CPCC07H17/08C07H1/00Y02P20/55
Inventor 任勇徐淑芬
Owner NINGXIA TAIYICIN BIOTECH CO LTD
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