(20S)-camptothecin derivatives and application thereof

A technology of camptothecin and its derivatives, applied in the field of pesticides, can solve problems such as great influence on the natural control ability of natural enemies, threats to human health, and destruction of ecological balance, and achieve excellent contact activity

Active Publication Date: 2015-07-08
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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  • (20S)-camptothecin derivatives and application thereof
  • (20S)-camptothecin derivatives and application thereof
  • (20S)-camptothecin derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Embodiment 1 camptothecin-20 (S)-O-2,2,3, the synthesis of 3-tetramethylcyclopropanyl carboxylate (a)

[0067] Describe the synthetic route of camptothecin-20(S)-O-2,2,3,3-tetramethylcyclopropanyl carboxylate (a) in detail below: add camptothecin (0.348g, 1mmol) and 4-dimethylaminopyridine (DMAP) (0.742g, 6mmol), pump out the air and replace it with N 2 Finally, 40 mL of dichloromethane and 2,2,3,3-tetramethylcyclopropanecarboxylic acid chloride (0.963 g, 6 mmol) were added, and the mixture was refluxed for 20 h under nitrogen protection. Add 80 mL of dichloromethane after the reaction, and then wash with 0.1 mol / L HCl. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated, and the solid was separated and purified by column chromatography (dichloromethane / methanol / petroleum ether=80 / 1 / 20), and finally 0.21 g of a light yellow solid was obtained. Yield 44.5%. 1 H NMR (DMSO-d 6 ,300MHz)δ0.94(6H,t,J=7.4Hz,H-18,CH 3 ),1.14(3H,s,CH 3 ),1....

Embodiment 2

[0069] Example 2 Synthesis of camptothecin-20 (S)-O-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanyl carboxylate (b)

[0070] The synthetic route of camptothecin-20(S)-O-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanyl carboxylate (b) is similar to a, and the column chromatography develops The agent is dichloromethane / methanol / petroleum ether=80 / 0.5 / 20), and finally 0.25 g of a light yellow solid was obtained, with a yield of 46.4%. 1 H NMR (DMSO-d 6 ,300MHz)δ0.96(3H,t,J=7.1Hz,H-18),1.12(3H,s,CH 3 ),1.20(3H,s,CH 3 ),1.31(1H,s,CHCOO),2.12(1H,s,CHCHCCl 2 ),2.21(2H,m,H-19),5.29(2H,s,H-5),5.49(2H,s,H-17),6.13(1H,m,CHCCl 2 ),6.99(1H,s,H-14),7.74(1H,t,J=7.0Hz,H-10),7.87(1H,t,H-11),8.13(each1H,t,J=7.5Hz ,H-12,H-7),8.67(1H,s,H-9); 13 C NMR (DMSO-d 6 ,75MHz)δ7.8(CH 3 ,C-18),20.1(CH 3 ,CH 3 ),20.2(CH 3 ,CH 3 ),21.9(C,C(CH 3 ) 2 ),22.0(CH,CHCHCCl 2 ), 30.2 (CH 2 ,C-19),33.0(C,CHCOO),50.5(CH 2 ,C-5),56.4(CH 2 ,C-17),76.3(C,C-20),94.8(CH,C-14),118.9(C,C-16),119.9(C,CHCCl 2...

Embodiment 3

[0072] Example 3 Camptothecin-20 (S)-O-3-(2-chloro-2-trifluoromethylvinyl)-2,2-dimethylcyclopropanyl carboxylate (c) synthesis

[0073] The synthetic route of camptothecin-20(S)-O-3-(2-chloro-2-trifluoromethylvinyl)-2,2-dimethylcyclopropanyl carboxylate (c) is similar to a, The developing solvent for column chromatography was ethyl acetate / petroleum ether=3 / 2, and finally 0.333 g of light yellow solid was obtained, with a yield of 58.1%. 1 H NMR (DMSO-d 6 ,300MHz)δ0.94(3H,t,J=7.4Hz,H-18),1.20(3H,s,CH 3 ),1.34(3H,s,CH 3 ),2.18(2H,m,H-19),2.37(1H,d,J=8.5Hz,CHCOO),2.56(1H,d,J=8.4Hz,CHCHC(CF 3 )Cl),5.28(2H,s,H-5),5.49(2H,s,H-17),6.59(1H,d,J=9.2Hz,CHC(CF 3)Cl),6.98(1H,s,H-14),7.73(1H,dd,J=8.0,1.0Hz,H-10),7.86(1H,t,J=1.4Hz,H-11),8.13 (each1H,t,J=8.1Hz,H-7,H-12),8.67(1H,s,H-9); 13 C NMR (CDCl 3 ,75MHz)δ7.2(CH 3 ,C-18),14.5(CH 3 ,CH 3 ), 18.8 (CH 3 ,CH 3 ),28.0(C,C(CH 3 ) 2 ),31.2(CH,CHCHC(CF 3 ) Cl), 31.6 (CH 2 ,C-19),32.0(CH,CHCOO),49.6(CH 2 ,C-5),66.8(CH 2 ,C-17),...

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Abstract

The invention relates to (20S)-camptothecin derivatives and an application thereof and belongs to the field of pesticides. In order to optimize the insecticidal activity of a plant source active substance (20S)-camptothecin, the camptothecin is spliced with active sites of a conventional chemical pesticide, namely a pyrethroid pesticide to obtain a series of pyrethroid-(20S)- camptothecine derivatives, so that the pyrethroid-(20S)-camptothecine derivatives maintain the original excellent antifeedant activity of the camptothecin to beet armyworms, can also be endowed with the excellent contact toxicity of the pyrethroid pesticide to the beet armyworms and have important research significance for the development of new high-efficiency low-toxicity pesticides with a unique targeting effect.

Description

technical field [0001] The invention relates to a (20S)-camptothecin derivative and application thereof, belonging to the field of pesticides. 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 have received widespread attention from all over the world. As an important means of production in the production of agricultural products - pesticides, therefore face There is a need to be both harmless to agricultural products and environmentally friendly while controlling pests. Therefore, the creation of "environmentally harmonious pesticides" or "biologically rational pesticides" with the advantages of high efficiency, low toxicity, low pollution, and high selectivity has become a general trend in the development of the pesticide industry in recent years. Plant-derived active su...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/22A01P7/04
Inventor 蒋红云邓丽张兰曹立东何伟志张燕宁
Owner INST OF PLANT PROTECTION CHINESE ACAD OF AGRI SCI
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