Novel Avermectin derivative and preparation method thereof

A technology of abamectin and its derivatives, which is applied in the field of novel abamectin derivatives and its preparation, can solve the problems of small advantages and short duration of action, and achieve quick effect, long duration of effect, and insecticidal spectrum wide effect

Active Publication Date: 2013-12-04
DAQING JEFENE BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the popularity and promotion of abamectin and its downstream products in recent years, its drug resistance has become more and more obvious. In addition, abamec...

Method used

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  • Novel Avermectin derivative and preparation method thereof
  • Novel Avermectin derivative and preparation method thereof
  • Novel Avermectin derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 1. Synthesis of C 5 -O-Allyl Abamectin B Formic Acid 2a (A is a single bond, R 1 is OH, 5, 22 and 23 are the serial numbers of carbons in the compound structure)

[0028] Reaction formula:

[0029]

[0030] 2. C 5 -O-Allyl Abamectin B Formic Acid 2a The preparation method:

[0031] A. Take 40g, 93.6% Abamectin B 2a Fine powder, dissolved in 200g of organic solvent dichloromethane, dissolved completely.

[0032] B. Cool the above solution to -15°C, add 12g of allyl chloroformate as a substitution reagent, stir for 1 hour, add 5.2g of acid-binding agent tetramethylethylenediamine dropwise, and control the reaction temperature in the range of -10~-5°C After the dropwise addition was completed, stirring was continued for 2 hours.

[0033] C. Add the reaction solution to 200mL sulfuric acid solution with a mass fraction of 2%, adjust the pH to 1-2 with sulfuric acid with a mass fraction of 98% under stirring, let stand to separate layers, and extract the water lay...

Embodiment 2

[0036] 1. Synthesis of C 5 -O-tert-butyldimethylsilyl abamectin B 2a (A is a single bond, R 1 is OH, 5, 22 and 23 represent the serial number of carbon in the compound structure)

[0037] Reaction formula:

[0038]

[0039] 2. C 5 -O-tert-butyldimethylsilyl abamectin B 2a preparation method

[0040] A. Take 40g, 93.6% Abamectin B 2a Fine powder, dissolved in 220g of organic solvent dichloroethane, dissolved completely.

[0041] B. Cool down the above solution to -15°C, add 10.2g of substitution reagent tert-butyldimethylsilyl chloride, stir for 1 hour, add 4.4g of acid-binding agent triethylamine dropwise, control the reaction temperature at -15~-10°C Within the range, stirring was continued for 2 hours after the dropwise addition was completed.

[0042] C. Add the reaction solution to 200mL, 2% sulfuric acid solution, adjust the pH to 1-2 with sulfuric acid under stirring, let stand to separate layers, extract the water layer once with 20mL dichloromethane, combine...

Embodiment 3

[0045] 1. Synthesis of C 5 -O-Formic acid methyl abamectin B 1a (A is a double bond, R 1 is H, 5, 22 and 23 are the serial numbers of carbons in the compound structure)

[0046] Reaction formula:

[0047]

[0048] 2. C 5 -O-Formic acid methyl abamectin B 1a The preparation method:

[0049] A. Take 40g, 94.3% Abamectin B 1a Fine powder, dissolved in 270g of organic solvent chloroform, dissolved completely.

[0050] B. Cool the above solution to -25°C, add 4.5g of methyl chloroformate as a substitution reagent, stir for 1 hour, then add 5.0g of acid-binding agent tetramethylethylenediamine dropwise, and control the reaction temperature in the range of -20~-15°C After the dropwise addition was completed, stirring was continued for 2 hours.

[0051] C. Add the reaction solution to 200mL, 2% sulfuric acid solution, adjust the pH to 1-2 with sulfuric acid under stirring, let it stand for stratification, extract the water layer with 30mL chloroform once, and add the combined...

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PUM

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Abstract

The invention relates to a novel Avermectin derivative and a preparation method thereof. The preparation method comprises the following steps: A, dissolving Avermectin B1a or Avermectin B2a into an organic solvent; B, cooling down the solution, adding a substitution reagent and dripping an acid-capturer; C, adding the reaction solution into a sulfuric acid solution, regulating pH, stilling, layering, extracting, adding an organic phase into an ammonia solution, regulating pH to be neutral, stilling, layering, extracting and merging the organic phase; D, performing distillation of the organic phase under reduced pressure to obtain the product. According to the invention, on the basis of the Avermectin B2a or B1a, C5-OH is subject to further chemical modification, and compared with the common Avermectin product, the novel Avermectin derivative has the advantages of high drug effect, broad insecticidal spectrum, good persistence, no residues, no pollution, high efficiency and no resistance. The novel Avermectin derivative has extremely high activity on many pests and mite, has the function of not only stomach toxicity but also killing and has a very good insecticide effect at a very low dosage.

Description

technical field [0001] The invention relates to an abamectin insecticide, in particular to a novel abamectin derivative and a preparation method thereof. Background technique [0002] Avermectin (AVM for short) is a low-toxicity, high-efficiency, high-selection, green, environmental-friendly and biological source insecticide, which completely solves the high toxicity, resistance and environmental impact of traditional pesticides. The issue of influence is a key research project of China's "Seventh Five-Year Plan", "Eighth Five-Year Plan", "Ninth Five-Year Plan", "Tenth Five-Year Plan" and "Eleventh Five-Year Plan". However, with the popularity and promotion of abamectin and its downstream products in recent years, its drug resistance has become more and more obvious. In addition, abamectin itself is very serious in thermal degradation and photodegradation, and its duration is short. Compared with chemical pesticides, its advantages are getting smaller and smaller. Content...

Claims

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Application Information

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IPC IPC(8): C07H17/08C07H1/00A01P7/04A01P7/02
Inventor 徐继民沈学庆徐龙广于鑫鑫
Owner DAQING JEFENE BIO CHEM
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