Rotenone oxime ether, preparation method and applications thereof

A technology for rotenone oxime ether and ketoxime ether, which is applied in the field of rotenone oxime ether and its preparation, can solve the problems of oxidative decomposition failure, unstable preparation concentration, and difficulty in standardization, and achieves improved stability, short reaction time and good stability. Effect

Inactive Publication Date: 2008-10-15
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 fail

Method used

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  • Rotenone oxime ether, preparation method and applications thereof
  • Rotenone oxime ether, preparation method and applications thereof
  • Rotenone oxime ether, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The synthesis of embodiment 1 rotenone oxime methyl ether (2)

[0019]

[0020] 25mL of acetone, 1.00g of rotenone oxime and 0.05g of tetramethylammonium bromide, 2mL of 50% sodium hydroxide solution, stirred for 30min. At 5°C, a solution of 0.38 g of dimethyl sulfate in 5 mL of acetone was added dropwise. After the dropwise addition was completed, the reaction was carried out at 0-5°C, followed by TLC, and the reaction was completed within 10 hours. After filtration, the filtrate was evaporated to dryness under reduced pressure, and the residue was poured into 50 mL of water. Solids were precipitated, filtered, washed with water, and dried to obtain 1.01 g of a light yellow solid with a yield of 98.06%. The melting point is 195-203°C. 1 H NMR (CDCl 3 ), δ: 1.75 (s, 3H, 8'CH 3 ), 2.99(dd, J=8.0Hz, J=16Hz, 1H, 4'-H), 3.28(dd, J=10.0Hz, J=16Hz, 1H, 4'-H), 3.75(s, 3H, OCH 3 ), 3.80 (s, 3H, OCH 3 ), 4.06 (s, 3H, NOCH 3 ), 4.23(d, J=12Hz, 1H, 6-H), 4.49(t, J=2.8Hz...

Embodiment 2

[0021] Example 2 1.5g of ketone oxime, 15ml of DMF, 0.2g of sodium hydroxide, stirred for 20min, 10ml of DMF solution containing 7.2mmol of iodomethane was added dropwise, reacted at room temperature for 3.0h, slowly added saturated saline to the reaction solution, and allowed to stand Separate the layers, filter, dry the filter cake, and recrystallize from ethanol to obtain 2 as a white solid.

Embodiment 3

[0022] Embodiment 3 The synthesis of rotenone oxime propyl ether (3)

[0023]

[0024] 20mL of acetone, 1.00g of rotenone oxime, 0.70g of potassium carbonate, 0.08g of potassium iodide and 0.90g of bromopropane were stirred and reacted under reflux, followed by TLC, and the reaction was completed in 18 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 1.02 g of a white solid, with a yield of 91.07%. The melting point is 209-214°C. 1 H NMR (CDCl 3 ), δ: 1.01 (t, J=4.4Hz, 3H, -CH 2 CH 3 ), 1.75 (m, 5H, 8'-CH 3 ,-CH 2 CH 3 ), 2.91(dd, J=8.0Hz, J=15.6Hz, 1H, 4'-H), 3.28(dd, J=10.0Hz, J=15.6Hz, 1H, 4'-H), 3.74(s, 3H, OCH 3 ), 3.80 (s, 3H, OCH 3 ), 4.22 (m, 3H, 6-H, OCH 2 ), 4.50(s, 1H, 12a-H), 4.59(dd, J=2.8Hz, J=12.4Hz, 1H, 6-H), 4.78(d, J=2.8Hz, 1H, 6a-H), 4.90(s, 1H, 7'-H), 5.05(s, 1H, 7'-H), 5.14...

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Abstract

The invention discloses a rotenone oxime-ether with chemical structural formula as showed on the right. The preparation method of rotenone oxime-ether I and II comprises the following steps of: allowing the rotenone oxime, catalyst, alkali and aldylating agent to react in solvent and to be filtered, washed and dried after the reaction; and the rotenone oxime-ether is obtained. New compounds of the rotenone oxime-ether can be used for preparing insecticide and fungicide.

Description

technical field [0001] The present invention relates to a new class of compound and its preparation method and application, specifically rotenone oxime ether 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 the c...

Claims

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Application Information

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IPC IPC(8): C07D493/14A01N43/90A01P7/00A01P3/00
Inventor 胡艾希王超邹孟欧晓明徐汉虹叶姣
Owner HUNAN UNIV
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