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Synthesis method and application of avermectin B2-based emamectin benzoate

A technology of emamectin and avermectin, applied in the field of organic synthesis, can solve the problems of great difference in activity and failure to be effectively utilized, and achieve low raw material cost, significant market advantage, and insecticidal activity high effect

Inactive Publication Date: 2019-03-15
王泊理
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Abamectin B 2 Homologs also have certain insecticidal activity, but with abamectin B 1 In comparison, its activity is very different, and it has not been effectively utilized and promoted. Because its price is relatively cheap, if it can be based on avermectin B 2 Isomers, effectively modifying its structure, improving its insecticidal activity and reducing toxicity, based on its price advantage, its development and application have very practical significance

Method used

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  • Synthesis method and application of avermectin B2-based emamectin benzoate
  • Synthesis method and application of avermectin B2-based emamectin benzoate
  • Synthesis method and application of avermectin B2-based emamectin benzoate

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Embodiment 1

[0049] The present embodiment based on Abamectin B 2 The preparation method of emamectin benzoate, described method comprises the steps:

[0050] (1) Hydroxyl protection reaction

[0051] Abamectin B 2 As a raw material, the hydroxyl groups at the 5th and 23rd positions were selectively protected by allyl chloroformate to obtain the intermediate I (5-allyl carboxyl abamectin B 2 and 5,23-dicarboxylate abamectin B 2 ).

[0052] Concrete reaction steps are briefly described as: 1mol avermectin B 2 Dissolve in dichloromethane, under the protection of argon, add 12 mol of triethylamine, then dropwise add 2 mol of allyl chloroformate, continue to pass in argon for 1 hour after the dropwise addition, and react in a closed system for 48 hours. After the reaction was completed, the solvent was removed to obtain the crude product, which was washed with dichloromethane and acetone to obtain the intermediate I (5-allyl carboxyl abamectin B 2 and 5,23-dicarboxylate abamectin B 2 )....

Embodiment 2

[0068] The present embodiment based on Abamectin B 2 The preparation method of emamectin benzoate, described method comprises the steps:

[0069] (1) Hydroxyl protection reaction

[0070] Abamectin B 2 As a raw material, the 5-position and 23-position hydroxyl groups are selectively protected by allyl chloroformate to obtain intermediate I (5-allyl carboxyl abamectin B 2 and 5,23-dicarboxylate abamectin B 2 ).

[0071] Concrete reaction steps are briefly described as: 10mmol abamectin B 2 Dissolve in dichloromethane, under the protection of argon, add 120mmol of triethylamine, then dropwise add 20mmol of allyl chloroformate, after the dropwise addition, continue to flow argon for 1 hour, then close the system for reaction for 48 hours. After the reaction was completed, the solvent was removed to obtain the crude product, which was washed with dichloromethane and acetone to obtain the intermediate I (5-allyl carboxyl abamectin B 2 and 5,23-dicarboxylate abamectin B 2 ). ...

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Abstract

The invention relates to a synthesis method and application of avermectin B2-based emamectin benzoate (YAB), and belongs to the technical field of organic synthesis. The preparation method comprises the following specific steps: sequentially performing a hydroxyl protection reaction, a hydroxyl oxidation reaction, a carbonyl amination reaction, an imine reduction and hydroxyl deprotection reactionand a salt formation reaction on avermectin B2 to obtain a target product YAB. Compared with the currently and widely used avermectin B1-based emamectin benzoate, the product YAB prepared by the synthesis method provided by the invention has the advantages of higher insecticidal activity, lower toxicity and low raw material cost and has significant market advantages.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular, relates to a 2 The synthetic method and application of emamectin benzoate. Background technique [0002] Avermectins (Avermectins) is a class of 16-membered macrolide compounds with insecticidal, acaricidal and nematicidal activities firstly developed by Satoshi Omura of Kitasato University in Japan and Merck Company of the United States. Produced by fermentation of the mold Streptomyces avermitilis. Natural abamectin contains 8 components, mainly 4 kinds namely A 1a 、A 2a , B 1a and B 2a , its total content ≥ 80%; the corresponding 4 smaller homologues are A 1b 、A 2b , B 1b and B 2b , and its total content ≤ 20%. B 1 and B 2 Compounds (including B 1a , B 1b , B 2a , B 2b ) structure as shown in the following formula 1, B 1a Molecular formula is C 48 h 72 o 14 , the molecular weight is 873.1; B 1b Molecular formula is C 47 h 70 o 14 , the molecular...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08C07H1/00A01N43/90A01P7/04A01P7/02
CPCC07H17/08A01N43/90C07H1/00
Inventor 王泊理
Owner 王泊理
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