4'-desoxy-4'-alkylated or acylated amino avermectin B2a/2b derivative, and preparation method and application thereof

A technology of acylated amine group and avermectin, which can be used in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., and can solve problems such as unutilized B2a/2b

Inactive Publication Date: 2015-11-11
HEBEI VEYONG BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these compounds in published patents and non-patent literature are all in the avermectin B 1a / 1b researched and developed on the parent body, there is a large amount of B in the fermentation process of abamectin 2a / 2b has been unused

Method used

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  • 4'-desoxy-4'-alkylated or acylated amino avermectin B2a/2b derivative, and preparation method and application thereof
  • 4'-desoxy-4'-alkylated or acylated amino avermectin B2a/2b derivative, and preparation method and application thereof
  • 4'-desoxy-4'-alkylated or acylated amino avermectin B2a/2b derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0078] Example 14 "-deoxy-4"-methylamino-23-acetoxy abamectin B 2a / 2b preparation of

[0079] 10.0g 4”-carbonyl-5-protected abamectin B 2a / 2b Dissolve in 120g sec-butyl acetate, cool down to 10°C, add 3.0g triethylamine, add DMAP as catalyst, add dropwise acetic anhydride (1.5g acetic anhydride dissolved in 10g sec-butyl acetate), after 2h, heat up to 60-70°C, add 1g of zinc trifluoroacetate and 5g of heptamethyldisilazane, after 6h, lower the temperature of the reaction solution to -10°C, add methanol, and add 0.8g of NaBH in batches 4 , reacted for 1h, raised the temperature to 0-5°C, added 0.005g tetrakistriphenylphosphine palladium, added 1.0g sodium borohydride in batches, and reacted for 1h, removed the 5-position protecting group, and terminated the reaction with 20% acetic acid solution. Adjust PH=2-3, then adjust PH=7-8 with 10% sodium hydroxide solution, and separate layers. The aqueous phase was extracted twice with 20g of sec-butyl acetate, the organic phases we...

Embodiment 24

[0080] Example 24"-deoxy-4"-(N-acetylmethylamino)-23-acetoxy abamectin B 2a / 2b Preparation of (preferred compound)

[0081] 11.5g 4"-methylamino-5-protected abamectin B 2a / 2b Dissolve in 90g of dichloromethane, cool down to 0°C, add 4.0g of triethylamine, dropwise add 3.4g of acetic anhydride, react for 2h, cool down the reaction solution to 0-5°C, add 10g of methanol, 0.005g of tetrakistriphenylphosphine Palladium, add 1.0g sodium borohydride in batches, after 1 hour, stop the reaction with 20% acetic acid solution, adjust PH=2-3, then adjust PH=7-8 with 10% sodium hydroxide solution, and separate layers. The aqueous phase was extracted twice with 20g of dichloromethane, the organic phases were combined, heated and distilled under reduced pressure, and the vacuum degree was 0.09MPa for 1h to obtain 8.6g of white solid, namely: 4”-deoxy-4”-(N-acetylmethylamino) -23-Acetoxyabamectin B 2a / 2b , the content is 95.0%, and the yield is 83.4%.

[0082] l HNMR (CDCl 3 ,500Hz)σ8....

Embodiment 34

[0083] Example 34 "-deoxy-4"-methylamino-23-O(C=O)CH 2 NMe 2 Abamectin B 2a / 2b preparation of

[0084] 11.0g 4"-carbonyl-5-protected abamectin B 2a / 2b Dissolve in 100g isopropyl acetate, keep warm at 30°C, add 3.0g anhydrous sodium carbonate, add DMAP, drop Cl(C=O)CH 2 NMe 2 1.3g, after 2h, add heptamethyldisilazane and zinc trifluoroacetate, raise the temperature to 60°C, react for 6h, lower the temperature, lower the temperature of the reaction solution to -10°C, add methanol, add 0.8gNaBH4 in batches, and react 1h, heat up to 0-5°C, add 0.005g tetrakistriphenylphosphine palladium, add 1.0g sodium borohydride in batches, react for 1h, remove the 5-position protecting group, and terminate the reaction with 20% acetic acid solution after the reaction , adjust PH=2-3, then adjust PH=7-8 with 10% sodium hydroxide solution, and separate layers. The aqueous phase was extracted twice with 20 g of isopropyl acetate, the organic phases were combined, heated and distilled under ...

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Abstract

The invention provides a 4'-desoxy-4'-alkylated or acylated amino substituted avermectin B2a / 2b derivative which is an alkylated or acylated avermectin B2a / 2b amino derivative synthesized by using methylamino avermectin B2a / 2b as a matrix. The 4'-desoxy-4'-alkylated or acylated amino substituted avermectin B2a / 2b derivative widens the utilization range of avermectin B2a / 2b, enhances the disinsection effect of the avermectin B2a / 2b and effectively prolongs the duration time of the product. The invention also provides a preparation method of the 4'-desoxy-4'-alkylated or acylated amino substituted avermectin B2a / 2b derivative and application of the 4'-desoxy-4'-alkylated or acylated amino substituted avermectin B2a / 2b derivative in preparing preparations for controlling pests of plants and animals.

Description

technical field [0001] The invention belongs to the technical field of agricultural chemicals and their preparation, and relates to abamectin B substituted by 4"-deoxy-4" alkylated or acylated amino groups 2a / 2b Derivatives and methods for their preparation. Background technique [0002] Avermectin is produced by Sterptomycesavermitills, which is a kind of streptomycin and belongs to streptomycin griseus. Abamectin is a mixture of fermentation components, a total of 8 components: A 1a 、A 1b 、A 2a 、A 2b , B 1a , B 1b , B 2a , B 2b . The abamectin exists in the mycelium of the fermented liquid, the filtrate is removed by filtration, the filter cake is extracted with a solvent, desugared, concentrated and crystallized to obtain the abamectin fine product. [0003] Avermectin is a neurotoxin, its mechanism is to act on the GABAA receptors of insect neuron synapses or neuromuscular synapses, interfere with the information transmission of nerve endings in insects, that i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08C07H1/00A01P7/04A01P7/02
Inventor 田学芳刘洁崔占卫杨建云次素英贾成国
Owner HEBEI VEYONG BIO CHEM
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