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Carboxylic acid rotenonoxime ester, method for preparing same and applications

A technology of rotenone oxime carboxylate and acid-binding agent, which is applied in the field of rotenone oxime carboxylate and its preparation, can solve the problems of difficult standardization, oxidative decomposition failure, and unstable preparation concentration, and achieve short reaction time and improved oxidation degradation , Synthetic operation is convenient

Inactive Publication Date: 2009-01-07
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still some problems in the use of rotenone, such as: rotenone is prone to oxidative decomposition and failure under natural conditions, so the concentration of the preparation is unstable, and it is not easy to standardize when used

Method used

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  • Carboxylic acid rotenonoxime ester, method for preparing same and applications
  • Carboxylic acid rotenonoxime ester, method for preparing same and applications
  • Carboxylic acid rotenonoxime ester, method for preparing same and applications

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Experimental program
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Effect test

Embodiment 1

[0018] The synthesis of embodiment 1 rotenone oxime propionate (1)

[0019]

[0020] 20mL of acetone, 1.00g of rotenone oxime, 0.70g of potassium carbonate, 0.05g of phase transfer catalyst tetramethylammonium bromide, stirred, 0.93g of propionic anhydride was added dropwise, stirred under ice water, followed by TLC, and the reaction was completed in 2 hours. The reaction solution was filtered, the filter cake was washed with acetone, the organic phases were combined, evaporated to dryness under reduced pressure to obtain a solid, washed with water, and dried to obtain 1.10 g of a white solid, with a yield of 96.5%. m.p.206~210℃; [α] D 25 +231.3 (AcOEt). 1 H NMR (CDCl 3 ), δ: 1.25 (t, J=7.6Hz, 1H, CH 3 ), 1.76 (s, 3H, 8'-CH 3 ), 2.53 (2×q, J=7.6Hz, 1H, COCH 2 ), 2.92(dd, J=8.0Hz, J=16Hz, 1H, 4'-H), 3.28(dd, J=10.0Hz, J=16Hz, 1H, 4'-H), 3.69(s, 3H, OCH 3 ), 3.81 (s, 3H, OCH 3 ), 4.28(d, J=12Hz, 1H, 6-H), 4.58(t, J=2.8Hz, 1H, 12a-H), 4.62(dd, J=12Hz, J=2.4Hz, 1H, 6- ...

Embodiment 2

[0021] The synthesis of embodiment 2 rotenone oxime propionate (1)

[0022] 20mL of N,N-dimethylformamide, 1.00g of rotenone oxime, 0.4g of pyridine, stirred for 30min, added dropwise 0.27g of propionic acid, stirred at 150°C, followed by TLC, and the reaction was completed in 2h. The reaction solution was filtered, the filter cake was washed with acetone, the organic phases were combined, evaporated to dryness under reduced pressure to obtain a solid, washed with water, and dried to obtain a white solid, m.p.206-209°C; [α] D 25 +231.3 (AcOEt), the spectrogram data is consistent with Example 1.

Embodiment 3

[0023] The synthesis of embodiment 3 rotenone oxime propionate (1)

[0024] 20mL chloroform, 1.00g rotenone oxime, 0.50g sodium carbonate, 0.05g phase transfer catalyst tetramethylammonium chloride, 0.93g propionic anhydride was added dropwise, stirred at 60°C, followed by TLC, and the reaction was completed in 2.5h. The reaction solution was filtered, the filter cake was washed with acetone, the organic phases were combined, evaporated to dryness under reduced pressure to obtain a solid, washed with water, and dried to obtain 8.8 g of a white solid, with a yield of 77.2%. m.p.206~210℃; [α] D 25 +231.3 (AcOEt), the spectrogram data is consistent with Example 1.

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Abstract

The invention discloses carboxylate elliptone oxime ester which has a following chemical structural formula. Carboxylate elliptone oxime ester 1 has a preparation method that elliptone oxime reacts with acylating agent through acid-binding agent and phase transfer catalyst, and carboxylate elliptone oxime ester is obtained through filtering, washing and drying after the reaction is completed. Carboxylate elliptone oxime ester which is a novel compound can be used for preparing pesticide.

Description

technical field [0001] The present invention relates to a new class of compound and its preparation method and application, specifically rotenone oxime carboxylate and its preparation method and application. Background technique [0002] Rotenone is a natural plant-based insecticide and acaricide. It is easy to degrade, accumulates in the environment with little toxicity, does not pollute the agricultural ecological environment and agricultural products, and is conducive to promoting ecological balance. However, there are still some problems in the use of rotenone, such as: rotenone is prone to oxidative decomposition and failure under natural conditions, so the concentration of the preparation is unstable, and it is difficult to standardize when used. Rotenone itself has good biological activity and is a very valuable compound. On the basis of mastering the relationship between the structure, stability and biological activity of rotenone, this project modified and modified...

Claims

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Application Information

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IPC IPC(8): C07D493/14A01N43/90A01P7/00
Inventor 胡艾希叶姣邹孟王超徐汉虹欧晓明
Owner HUNAN UNIV
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