Camptothecin derivative and preparation method thereof

A derivative, camptothecin technology, applied in the field of pesticides, can solve the problems of great influence on the natural control ability of natural enemies, environmental pollution, unreasonable use of chemical pesticides, etc., and achieve the effect of excellent contact activity and simple synthesis method

Inactive Publication Date: 2015-03-04
INST OF PLANT PROTECTION CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But for a long time, due to the large and unreasonable use of chemical pesticides, the beet armyworm has developed resistance to it rapidly, and the level of resistance is also increasing
According to reports, the beet armyworm has produced varying degrees of resistance to organochlorine, carbamate, organophosphorus, pyrethroids and other chemical pesticides, as well as Bacillus thuringiensis and abamectin, which have caused farmers to struggle in the control process. The continuous increase in the dosage of pesticides has a great impact on natural enemies and the natural control ability of the agricultural ecosystem, polluting the environment, threatening human health, and destroying the ecological balance.

Method used

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  • Camptothecin derivative and preparation method thereof
  • Camptothecin derivative and preparation method thereof
  • Camptothecin derivative and preparation method thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0034] The present invention also provides a preparation method of the camptothecin derivative, and its synthetic route is as follows:

[0035]

[0036] Wherein, R is selected from one of C1-C8 linear alkanes and monohalogenated C1-C8 linear alkanes.

Embodiment 1

[0037] Example 1 (Preparation method of compound 27)

[0038] synthetic route

[0039]

[0040] Dissolve 364mg (1mmol) of 10-hydroxycamptothecin in 120ml of anhydrous tetrahydrofuran (THF), add 0.5ml of triethylamine, take out the air and change into N 2 Then, 430 mg (6 mmol) of propyl isocyanate was slowly added dropwise, and the reaction was carried out at room temperature for 24 hours. After the reaction is over, add 80mL of dichloromethane, dry the organic phase with anhydrous sodium sulfate, then filter, rotary evaporation and concentrate the organic layer to obtain a solid. Finally, the concentrated solid is separated and purified by silica gel column chromatography (the elution machine is two Methyl chloride / methanol / petroleum ether=80 / 1 / 20) to obtain 0.17 g of a light yellow solid.

[0041] The structural formula of the resulting product is:

[0042]

[0043] NMR data: 1 H NMR (DMSO-d6, 300MHz) δ 0.89 (6H, m, H-18), 1.53 (2H, m), 1.87 (2H, m, H-19), 3.09 (2H, m), 5.30 (2H , ...

Embodiment 2

[0044] Example 2 (Preparation method of compound 134)

[0045] synthetic route

[0046]

[0047] Dissolve 364mg (1mmol) of 10-hydroxycamptothecin in 120ml of anhydrous tetrahydrofuran (THF), add 0.5ml of triethylamine, take out the air and change into N 2 Then, 723 mg (6 mmol) of ethyl chloroisocyanate was slowly added dropwise, and the reaction was carried out at room temperature for 24 hours. After the reaction is over, add 80mL of dichloromethane, dry the organic phase with anhydrous sodium sulfate, then filter, rotary evaporation and concentrate the organic layer to obtain a solid. Finally, the concentrated solid is separated and purified by silica gel column chromatography (the elution machine is two Methyl chloride / methanol / petroleum ether=80 / 1 / 20) to obtain 0.22 g of light yellow solid.

[0048] The structural formula of the resulting product is:

[0049]

[0050] NMR data: 1 H NMR (DMSO-d6, 300MHz) δ 0.87 (3H, m, H-18), 1.88 (2H, m, H-19), 3.58 (2H, m), 3.71 (2H, m), 5.29 (2H...

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Abstract

The invention discloses a camptothecin derivative as well as a preparation method and an application thereof. The structural formula of the camptothecin derivative is shown in the specification, wherein R is one of C1-C8 straight-chain paraffin and halogenated C1-C8 straight-chain paraffin. According to the preparation method disclosed by the invention, 10-camptothecin is taken as a lead compound and is structured to synthesize a novel camptothecin derivative; the synthesis method is simple and convenient; due to structural modification, the camptothecin derivative can maintain the original excellent antifeedant activity of the camptothecin for asparagus caterpillar and can also have the excellent contact toxicity for asparagus caterpillar; therefore, the camptothecin derivative has an important research significance in development of a novel high-efficiency and low-toxin pesticide which has a unique acting target, and has an important practical value in the field of pesticides.

Description

Technical field [0001] The invention relates to the field of pesticides, in particular to camptothecin derivatives and a preparation method thereof. Background technique [0002] With the continuous improvement of people’s quality of life and the pursuit of a better living environment, the production of green and pollution-free agricultural products and the protection of the environment from pollution damage have received universal attention from all over the world. As an important means of production in the production of agricultural products, pesticides face While controlling pests, it must be harmless to agricultural products and environmentally friendly. Therefore, the preparation of "environmentally harmonious pesticides" or "biologically reasonable pesticides" with the advantages of high efficiency, low toxicity, low pollution, and high selectivity has become the general trend of the development of the pesticide industry in recent years. Plant-derived active substances are ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/22A01P7/04
CPCC07D491/22
Inventor 梅向东蒋红云张兰张燕宁张兰祥宁君
Owner INST OF PLANT PROTECTION CHINESE ACAD OF AGRI SCI
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