Unlock instant, AI-driven research and patent intelligence for your innovation.

Avermectin benzoate compounds and synthetic method thereof

A technology of abamectin and benzoate, applied in the field of abamectin benzoate compound and its synthesis, can solve the problems of no practical use value, no insecticidal efficacy and high cost, and achieve reliable prevention and control. Effective, good insecticidal effect, high efficacy

Active Publication Date: 2014-02-05
DAQING JEFENE BIO CHEM
View PDF2 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although other various modification schemes are often seen in journals, they either have high cost, low yield, and no practical value; or have no insecticidal effect

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Avermectin benzoate compounds and synthetic method thereof
  • Avermectin benzoate compounds and synthetic method thereof
  • Avermectin benzoate compounds and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1. Synthesis of HO-C 5 -AVM-C 4 - Benzoate Abamectin B 2a (A is a single bond, R 1 is OH, 4, 5, 22 and 23 are the serial numbers of carbons in the compound structure)

[0030] Reaction formula:

[0031]

[0032] 2. HO-C 5 -AVM-C 4 - Benzoate Abamectin B 2a The preparation method:

[0033] A, the fine powder of Abamectin B2a of 40g93.6% is dissolved in the organic solvent methylene chloride of 200g, until fully dissolving.

[0034] B. Cool the above solution to -25~-5°C, first add 7g allyl chloroformate, after stirring for half an hour, add 5g allyl chloroformate and 7g tetramethylethylenediamine dropwise at the same time, control the reaction temperature to -25~-15°C, continue to stir and react for 15 minutes after the dropwise addition is completed; after the reaction is qualified, use a phosphoric acid solution with a mass fraction of 12% to terminate, extract the organic phase with a saturated sodium bicarbonate solution after layering, and then extract th...

Embodiment 2

[0038] 1. Synthesis of HO-C 5 -AVM-C 4 - Benzoate Abamectin B 2a (A is a single bond, R 1 is OH, 4, 5, 22 and 23 are the serial numbers of carbons in the compound structure)

[0039] Reaction formula:

[0040]

[0041] 2. HO-C 5 -AVM-C 4 - Benzoate Abamectin B 2a The preparation method:

[0042] A, the fine powder of Abamectin B2a of 40g93.6% is dissolved in the organic solvent methylene chloride of 200g, until fully dissolving.

[0043]B. Cool the above solution to -25~-5°C, first add 6g allyl chloroformate, after stirring for half an hour, add 4g allyl chloroformate and 6g tetramethylethylenediamine dropwise at the same time, control the reaction temperature to -25~-15°C, continue to stir and react for 15 minutes after the dropwise addition is completed; after the reaction is qualified, use a phosphoric acid solution with a mass fraction of 12% to terminate, extract the organic phase with a saturated sodium bicarbonate solution after layering, and then extract the...

Embodiment 3

[0047] 1. Synthesis of CH 2 C(CH 3 )OCOO-C 5 -AVM-C 4 - Benzoate Abamectin B 1a (A is a single bond, R 1 is OH, 4, 5, 22 and 23 are the serial numbers of carbons in the compound structure)

[0048] Reaction formula:

[0049]

[0050] 2. CH 2 C(CH 3 )OCOO-C 5 -AVM-C 4 - Benzoate Abamectin B 1a The preparation method:

[0051] A, the fine powder of Abamectin B1a of 40g90.9% is dissolved in the organic solvent methylene chloride of 200g, until fully dissolving.

[0052] B. Cool the above solution to -25~-5°C, first add 7g allyl chloroformate, after stirring for half an hour, add 5g allyl chloroformate and 7g tetramethylethylenediamine dropwise at the same time, control the reaction temperature to -25~-15°C, continue to stir and react for 15 minutes after the dropwise addition is completed; after the reaction is qualified, use a phosphoric acid solution with a mass fraction of 12% to terminate, extract the organic phase with a saturated sodium bicarbonate solution a...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to avermectin benzoate compounds and a synthetic method thereof. The method comprises the following steps of (A) dissolving avermectin in an organic solvent; (B) reducing the temperature, adding a protective agent, dripping an acid-binding agent, ending after the reaction is qualified, extracting and drying; (C) dissolving a dried material in the organic solvent, reducing the temperature, adding an acid-binding agent and a catalyst, and dripping benzoyl chloride; (D-1) adding a hydrochloric acid solution, standing for layering, adding a sodium bicarbonate solution for extracting, standing for layering, and performing vacuum drying on an organic phase, thereby obtaining a product containing a protecting group in a C5 position; (D-2) adding a mixed solution of sodium borohydride and methanol into the solution in the step (C), adding tetra(triphenyl phosphate) palladium, adding an acetic acid solution into the reaction solution and ending after the reaction is ended, standing, regulating a pH value to be 8 by using sodium hydroxide, standing for layering, and performing vacuum drying on the organic phase, thereby obtaining a product without the protecting group in the C5 position. The avermectin benzoate compound has the advantages of high pesticide effect, wide insecticidal spectrum, high persistence, no residue, no pollution, high effect taking speed and no resistance. Common insect pests such as red and white spiders, plutella xylostella, rice leaf folder, rice stem borers and the like are prevented and controlled.

Description

technical field [0001] The invention relates to abamectin insecticides, in particular to a class of abamectin benzoate compounds and a synthesis 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. T...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D493/22A01P7/04
CPCA01N43/90A01N47/06C07H1/00C07H17/08Y02P20/55
Inventor 徐继民
Owner DAQING JEFENE BIO CHEM