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A new class of compounds with 5-oxime ester b2a structure and their preparation methods and applications

A compound and reaction technology, applied in the field of compounds with 5-oxime ester B2a structure, can solve the problems of low application value, waste of resources, environmental pollution and the like

Active Publication Date: 2019-08-20
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, B2 (B2a ≥ 95%, B2b ≤ 5%), which accounts for more than one-third of the total amount in the production of abamectin, has long been used as an auxiliary material for B1 in the form of "ointment" because of its low application value. Pushing to the market, causing environmental pollution and serious waste of resources

Method used

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  • A new class of compounds with 5-oxime ester b2a structure and their preparation methods and applications
  • A new class of compounds with 5-oxime ester b2a structure and their preparation methods and applications
  • A new class of compounds with 5-oxime ester b2a structure and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Example 1. Preparation and structure identification of compound CAU-AVM-01 (R=phenyl in formula I)

[0093] according to figure 1 The synthetic route shown is the synthesis of compound CAU-AVM-01.

[0094] (1) Add B2a (6g, 6.7mmol) in a 250ml round bottom flask, dissolve in 45ml of anhydrous dichloromethane, then add triethylamine (1.0g, 10mmol), and slowly Add allyl chloroformate (0.97g, 8mmol) dropwise, continue the reaction for 40min after the drop, TLC monitors that the reaction is complete, add 1ml of methanol to quench, extract with dichloromethane, wash with 1N hydrochloric acid, saturated sodium chloride solution, and water successively The organic phase was dried over anhydrous sodium sulfate, dichloromethane was distilled off, and purified by column chromatography to obtain 6.1 g of light yellow solid 5-O-Alloc avermectin B2a with a yield of 93%. Dissolve 5-O-Alloc avermectin B2a (6.0g, 6.2mmol) in 40ml DMF, add triethylamine (4.4g, 43mmol), place the reacti...

Embodiment 2

[0103] Example 2. Preparation and structural identification of compound CAU-AVM-18 (R=phenyl in formula II)

[0104] according to figure 2 The synthetic route shown shows the synthesis of compound CAU-AVM-18.

[0105] (1) Dissolve 5-O avermectin B2a (4g, 3.6mmol) in 3% sulfuric acid methanol solution, react at -5°C for 24h, neutralize with triethylamine, concentrate, extract with dichloromethane, anhydrous sodium sulfate After drying, filtering and concentrating, column chromatography gave 2.3 g of light yellow solid 5-O avermectin B2a monosaccharide, with a yield of 85%.

[0106] (2) Dissolve 5-O avermectin B2a monosaccharide (1.7g, 2.3mmol) in 10ml MeOH and 10ml 1,4-dioxane solution; dissolve hydroxylamine hydrochloride (0.94g, 13mmol) in 8ml water, and then It was added dropwise into the reaction system, TLC detected that the reaction was complete, concentrated, diluted with dichloromethane, washed with water, the aqueous layer was extracted twice with dichloromethane, t...

Embodiment 3

[0112] Example 3, Preparation and Structure Identification of Compound CAU-AVM-35 (R=Phenyl in Formula III)

[0113] according to image 3 The synthetic route shown is the synthesis of compound CAU-AVM-35.

[0114] (1) Dissolve 5-O avermectin B2a (4g, 3.6mmol) in 5% sulfuric acid methanol solution, react at -5°C for 24h, neutralize with triethylamine, concentrate, extract with dichloromethane, anhydrous sodium sulfate After drying, filtering and concentrating, column chromatography gave 2.0 g of light yellow solid 5-O avermectin B2a aglycone with a yield of 93%.

[0115] (2) Dissolve 5-O avermectin B2a aglycone (1.4g, 2.3mmol) in 10ml MeOH and 10ml 1,4-dioxane solution; dissolve hydroxylamine hydrochloride (0.94g, 13mmol) in 8ml water, and then It was added dropwise into the reaction system, TLC detected that the reaction was complete, concentrated, diluted with dichloromethane, washed with water, the aqueous layer was extracted twice with dichloromethane, the organic phase ...

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Abstract

The invention provides a class of compounds with novel 5-oxime ester B2a structures, preparation methods of the compounds and applications that the compounds are used as insecticides, acaricides and nematicides. Structural formulae of the compounds are represented as a formula I, a formula II or a formula III. According to the invention, the structure of B2a, a byproduct of avermectin productive process, is optimized; a series of 5-oxime ester B2a compounds with novel structures is designed and synthesized; comprehensive insecticidal activity determination is performed on the compounds; and compounds with good pesticide effects are found. The reaction route is simple; the products have good insecticidal activity; the biological activity ratio of most compounds surpasses a control insecticide avermectin; and the biological activity increases obviously, and therefore, the compounds provided by the invention have very high pesticide researching value.

Description

technical field [0001] The invention relates to a novel compound of 5-oxime ester B2a structure, its preparation method and its application as insecticide, acaricide and nematicide. Background technique [0002] Abamectin is a group of sixteen-membered macrolide compounds fermented by Streptomyces avermitilis, which consists of 8 homologues with similar structures (A1a, A1b, A2a, A2b, B1a, B1b, B2a, B2b). Abamectin has good insecticidal, acaricidal and antiparasitic activities, and is safe for mammals. Its mechanism of action is to stimulate the release of γ-aminobutyric acid (GA-BA) from nerve endings and regulate glutamate gating Chloride ion channels promote the opening of GABA-gated chloride ion channels and glutamate-gated chloride ion channels, and the influx of a large amount of chloride ions causes the neural membrane potential to be supercharged, causing the neural membrane to be in a state of inhibition, paralyzing and killing insects. [0003] my country is a bi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/08C07H1/00A01N43/90A01P7/04A01P7/02A01P5/00
CPCA01N43/90C07H1/00C07H17/08Y02A40/70Y02P20/55
Inventor 张建军孙国绍金淑惠徐鑫王道全
Owner CHINA AGRI UNIV
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