Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Abamectin B2 derivatives as well as preparation method and application thereof

A technology of abamectin and derivatives, applied in the field of abamectin B2 derivatives and preparation thereof, can solve problems such as pollution, waste of resources, environment and the like

Active Publication Date: 2021-10-29
HEBEI VEYONG BIO CHEM
View PDF13 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After the abamectin B1 is extracted from the fermentation broth, more than 20% of the abamectin B2 contained therein will be shelved or discarded in large quantities, resulting in a huge waste of resources and environmental pollution

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
  • Abamectin B2 derivatives as well as preparation method and application thereof
  • Abamectin B2 derivatives as well as preparation method and application thereof
  • Abamectin B2 derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] The present embodiment provides a kind of preparation method of the compound shown in formula (II):

[0085] When R2 is a hydroxyl group, it may comprise the following steps:

[0086] Take 10g of Abamectin B2a / 2b raw material and add it to 50g of dichloromethane, stir to dissolve, then add 1.7g of tetramethylethylenediamine, cool down to -15℃~-10℃, slowly add 1.6g of allyl chloroformate dropwise ester, after the dropwise addition, keep warm for 30min, then add 2.6g dimethyl sulfoxide, then slowly add 2.0g phenyl phosphate dichloride dropwise, keep warm for 1h, add 50mL water, stir at room temperature for 30min, then separate the phases, and separate the organic phase After drying over anhydrous magnesium sulfate, it was concentrated to dryness to obtain 10.3 g of light yellow solid;

[0087] Add the solid obtained in the previous step into 50mL of isopropyl acetate, stir to dissolve, add 0.5g of zinc acetate and 3.0g of hexamethyldisilazane, heat up and reflux for 6 ho...

Embodiment 2

[0095] A preparation method of Abamectin B2 derivatives, comprising the following steps:

[0096] Step 1, the preparation of 4"-acetylamino-5-allyloxycarbonyl abamectin B2a / B2b:

[0097] 39.2g (40.8mmol) 4"-amino-5-allyloxycarbonyl Abamectin B2a / B2b (4"--amino-5-allyloxycarbonyl Abamectin B2a content greater than 95%) was added to In 120g of dichloromethane, cool the reaction solution to 0°C, add 5.2g (44.7mmol) tetramethylethylenediamine, under the protection of nitrogen, slowly add 3.5g of acetyl chloride (44.7mmol), and react at 0°C after the dropwise addition 2h, get the reaction solution containing 4"-acetylamino-5-allyloxycarbonyl abamectin B2a / B2b;

[0098] Take a small amount of the above reaction solution and confirm its structure after concentration and drying:

[0099] MS[M+H + ] (m / z): 1003.55.

[0100] 1 H NMR (500MHz, CDCl 3 )δ6.77(s,1H),5.96(ddt,J=16.6,10.4,6.2Hz,1H),5.78–5.70(m,2H),5.42(p,J=7.0Hz,1H),5.32–5.19 (m,4H),5.20–5.12(m,2H),5.03–4.95(m,3H),4.92–4....

Embodiment 3

[0111] A preparation method of Abamectin B2 derivative (5-hydroxylamine subunit-4 "-acetamido Abamectin B2a / B2b), comprising the following steps:

[0112] Step 1, 49.3g (0.05mol) 5-allyloxyimino-4 "-aminoabamectin B2a / B2b (5-allyloxyimino-4"-aminoabamectin B2a content Not less than 95%) was added to 446g of dichloromethane, the reaction solution was cooled to -5°C, 5.8g (0.05mol) of tetramethylethylenediamine was added, and 12.6g of trifluoroacetic anhydride (0.06mol) was slowly added, After the dropwise addition, the reaction was incubated and stirred for 30 minutes, and the remaining amount of 5-allyloxyimino-4"-aminoabamectin B2a / B2b was detected by high-performance liquid chromatography. The remaining amount of B2a / B2b was less than 1%. The reaction solution of hydroxylamine subunit-4"-acetamidoabamectin B2a / B2b;

[0113] Step 2. Cool the reaction solution containing 5-allyloxyhydroxylamine subunit-4"-acetamidoabamectin B2a / B2b in step 1 to 0°C, add 13g of methanol (0.4mo...

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

PropertyMeasurementUnit
Wavelengthaaaaaaaaaa
Login to View More

Abstract

The invention provides abamectin B2 derivatives as well as a preparation method and application thereof. The structure of the abamectin B2 derivatives is shown as a formula (I). The abamectin B2 with low availability in the abamectin production process is subjected to structure optimization, a series of abamectin B2 derivatives with brand-new structures are designed and synthesized, and the abamectin B2 derivatives have stable chemical properties, higher insecticidal activity and more excellent insecticidal persistence, can effectively prevent and treat various in-vivo and in-vitro parasites such as parasites, lice, mites and flies of livestock, especially have a special effect on cow nematode diseases, are a novel and efficient abamectin biopesticide, have a very high pesticide research value, and have a wide application prospect in agriculture and livestock industry.

Description

technical field [0001] The invention relates to the field of agricultural chemicals and preparation technology, in particular to a derivative of avermectin B2 and its preparation method and application. Background technique [0002] Severe pests are often encountered in the production process of animal husbandry. The pests take the nutrition of the animal body through parasitism and other means. Or the excrement is toxic to livestock, causing malnutrition, emaciation, weakness and even death. Currently the most commonly used method of effectively controlling livestock pests and diseases is the use of insecticides or repellents. [0003] Acetaminobamectin is the first broad-spectrum antiparasitic drug developed by Merck in 1997 that can be applied to dairy and beef cattle without drug withdrawal period. On the basis of the structure of Abamectin B1, acetyl Abamectin was obtained by modifying its 4” position with acetyl group. Acetyl Abamectin is an efficient, broad-spectrum...

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): C07H1/00C07H17/08A61K31/7048A61P33/14A61P33/00
CPCC07H1/00C07H17/08A61P33/14A61P33/00Y02A40/70Y02P20/55
Inventor 王博高永民杨锦蓉张庆李志峰范朝辉李立华田学芳贾成国
Owner HEBEI VEYONG BIO CHEM
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com