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Carbamic tubatoxin oxime ester, preparation and application thereof

A technology for rotenone oxime carbamate and aryl ester, which is applied to the field of new compounds and their preparation, can solve problems such as difficulty in standardization, oxidative decomposition failure, unstable preparation concentration, etc., and achieves short reaction time, improved biological activity, and improved synthesis Easy-to-use effects

Inactive Publication Date: 2009-01-14
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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  • Carbamic tubatoxin oxime ester, preparation and application thereof
  • Carbamic tubatoxin oxime ester, preparation and application thereof
  • Carbamic tubatoxin oxime ester, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0019]

[0020] Stir 1.0 g of rotenone oxime with 10.0 ml of acetone or benzene, dissolve, add dropwise 10 ml of acetone solution containing methyl isocyanate, and reflux for 1 hour. TLC monitors the reaction process. The reaction solution was filtered, the filtrate was rotary evaporated to remove the solvent, and the obtained white solid was washed with water. 1 H-NMR (CDCl 3 , 400MHz) δ: 2.75 (s, 3H, CH 3 ), 2.93(dd, J=8.0Hz, J=15.6Hz, 1H, 4'-H), 3.28(dd, J=10.0Hz, J=15.6Hz, 1H, 4'-H), 3.71(s, 3H, OCH 3 ), 3.80 (s, 3H, OCH 3 ), 4.22 (d, J=12Hz, 1H, 6-H), 4.56 (d, J=2.8Hz, 1H, 12a-H), 4.60 (dd, J=12Hz, J=2.8Hz, 1H, 6- H), 4.92(s, 2H, 6a-H, 7'-H), 5.06(s, 1H, 7'-H), 5.17(t, J=8.8Hz, 1H, 5'-H), 6.35( d, J=8.0Hz, 1H, NH), 6.41(s, 1H, 4-H), 6.41(s, 1H, 1-H), 6.48(d, J=8.8Hz, 1H, 10-H), 7.76 (d, J = 8.4 Hz, 1H, 11-H).

Embodiment 2

[0021] The synthesis of embodiment 2 cyclohexylcarbamate rotenone oxime ester (2)

[0022]

[0023] Rotenone oxime 1.0g, acetone or tetrahydrofuran 10.0ml, stir, dissolve, add 10ml acetone solution containing 0.3g cyclohexyl isocyanate, reflux reaction for 7h, add 0.3g cyclohexyl isocyanate, continue reaction for 2h, TLC monitoring reaction process. The reaction liquid was filtered, the filtrate was rotary evaporated to remove the solvent, the white solid obtained was washed with water, and recrystallized from ethanol to obtain 1.0 g of white powder with a melting point of 185-188°C and a yield of 77.0%. 1 H-NMR (CDCl 3 , 400MHz) δ: 1.24~1.44 (m, 4H, c-C 6 h 11 ), 1.64 (m, 4H, c-C 6 h 11 ), 1.76 (s, 3H, 8'-CH 3 ), 1.78 (m, 1H, c-C 6 h 11 ), 2.06(m, 2H, c-C 6 h 11 ), 2.93(dd, J=8.0Hz, J=15.6Hz, 1H, 4'-H), 3.28(dd, J=10.0Hz, J=15.6Hz, 1H, 4'-H), 3.71(s, 3H, OCH 3 ), 3.80 (s, 3H, OCH 3 ), 4.22 (d, J=12Hz, 1H, 6-H), 4.56 (d, J=2.8Hz, 1H, 12a-H), 4.60 (dd, J=12Hz, J...

Embodiment 3

[0024] The synthesis of embodiment 3 octylcarbamic acid rotenone oxime ester (3)

[0025]

[0026] Stir 0.8g of rotenone oxime, 30.0ml of acetone or N-methylpyrrolidone, dissolve, add 0.3g of octyl isocyanate, reflux for 5 hours, add 0.15g of octyl isocyanate, continue the reaction for 10 hours, and monitor the reaction process by TLC. The reaction solution was filtered, the filtrate was rotary evaporated to remove the solvent, the white solid obtained was washed with water, and recrystallized from ethanol to obtain 0.96 g of white powder with a melting point of 140-143° C. and a yield of 86.8%. 1 H-NMR (CDCl 3 , 400MHz) δ: 0.89 (t, J=6.8Hz, 3H, CH 3 ), 1.30(m, 10H, 5×CH 2 ), 1.65 (m, 2H, CH 2 ), 1.76 (s, 3H, 8'-CH 3 ), 2.93(dd, J=8.0Hz, J=16Hz, 1H, 4'-H), 3.29(dd, J=9.6.Hz, J=16Hz, 1H, 4'-H), 3.37(q, J =6.8Hz, 2H, NCH 2 ), 3.71 (s, 3H, OCH 3 ), 3.80 (s, 3H, OCH 3 ), 4.23 (d, J=12Hz, 1H, 6-H), 4.57 (d, J=2.4Hz, 1H, 12a-H), 4.60 (dd, J=12Hz, J=2.4Hz, 1H, 6- H), 4.92...

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Abstract

The invention discloses a carbamic acid rotenone oxime ester having a chemical structural formula and a stereoscopic structural formula as shown in a formula I, and a preparation method of carbamic acid rotenone oxime ester I comprises the reaction between rotenone oxime and isocyanate in the presence of a phase-transfer catalyst or an acid binding agent. The carbamic acid rotenone oxime ester is obtained through filtration, washing and drying after the reaction is finished. The new carbamic acid rotenone oxime ester compound can be used for preparing pesticides and bactericides.

Description

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

Claims

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Application Information

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IPC IPC(8): C07D493/14A01N43/24A01P7/00A01P3/00
Inventor 胡艾希王超叶姣徐汉虹欧晓明
Owner HUNAN UNIV
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