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10-hydroxycamptothecine derivatives and applications thereof

A technology of hydroxycamptothecin and derivatives, applied in the field of pesticides, can solve the problems of the great influence of natural enemies' natural control ability, increase the dosage of drugs, environmental pollution, etc., and achieve the effect of excellent contact killing activity

Active Publication Date: 2013-09-04
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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  • 10-hydroxycamptothecine derivatives and applications thereof
  • 10-hydroxycamptothecine derivatives and applications thereof
  • 10-hydroxycamptothecine derivatives and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] 10-[(2,2,3,3-Tetramethylcyclopropanyl)carboxylate]-(20S)-camptothecin (a) synthetic route: In a 250mL flask, add 10-hydroxycamptothecin ( 0.364g, 1mmol), the reaction bottle was pumped out of the air into the N 2 After that, 120 mL of tetrahydrofuran (THF), fenchromoyl chloride (0.96 g, 6 mmol) and triethylamine (Et 3 N) 0.9 mL. N 2 The reaction was stopped after reflux under protection for 4 hours. The reaction solution was transferred to a 500mL separatory funnel, 180mL ethyl acetate was added, and the mixture was evenly shaken. Then add 40 mL of distilled water, oscillate and mix completely, let stand to separate the liquid, take the upper organic phase, and repeat three times. The organic phase was transferred into a 500mL Erlenmeyer flask, and anhydrous sodium sulfate was added for shaking, left to stand, filtered, and the solution was rotary evaporated to obtain a light yellow solid. Add 20 mL of anhydrous diethyl ether to the solid, stir magnetically for 10 ...

Embodiment 2

[0064] 10-[[3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanyl]carboxylate]-(20S)-camptothecin (b) synthetic route: in a 250mL flask , added 10-hydroxycamptothecin (0.36g, 1mmol), the reaction flask was pumped out the air into N 2 Then, 120 mL of tetrahydrofuran, chrysanthemum acid chloride (1.35 g, 6 mmol) and 0.9 mL of triethylamine were added. N 2 The reaction was stopped after reflux under protection for 6 hours. The reaction solution was transferred to a 500mL separatory funnel, 180mL ethyl acetate was added, and the mixture was evenly shaken. Then add 40 mL of distilled water, oscillate and mix completely, let stand to separate the liquid, take the upper organic phase, and repeat three times. The organic phase was transferred into a 500mL Erlenmeyer flask, added anhydrous sodium sulfate to remove water, filtered and evaporated to dryness, and then passed through a silica gel column (dichloromethane / methanol / petroleum ether=70 / 0.5 / 30) to obtain 0.28g of a light yellow sol...

Embodiment 3

[0066] 10-[[3-(2-Chloro-2-trifluoromethylvinyl)-2,2-dimethylcyclopropanyl]formyl]-(20S)-camptothecin (c) synthetic route Similar to b, the column chromatography developing solvent is dichloromethane / methanol / petroleum ether=100 / 0.5 / 80), and finally 0.32 g of light yellow solid was obtained, with a yield of 55.1%. 1 H NMR (CDCl 3 ,300MHz)δ1.00(3H,t,J=7.4Hz,H-18),1.42,1.46(each3H,s,CH 3 ),1.89(2H,m,H-19),2.32(1H,d,J=8.3Hz,CHCOO),2.41(1H,t,J=8.7Hz,CHCHC(CF 3 )Cl), 4.39(1H,s,OH), 5.26(2H,s,H-5), 5.30(2H,s,H-17), 5.70(1H,d,CHC(CF 3 )Cl),6.95(1H,d,H-14),7.63(1H,s,H-11),7.71(1H,s,H-9),8.23(1H,d,J=9.2Hz,H- 12),8.30(1H,d,J=2.9Hz,H-7); 13 C NMR (CDCl 3 ,75MHz)δ7.7(CH 3 ,C-18),14.8(CH 3 ,2CH 3 ),28.3(C,C(CH 3 ) 2 ),28.8(CH 2 ,C-19),31.7(CH,CHCHC(CF 3 )Cl), 32.6(CH,CHCOO), 50.0(CH 2 ,C-5),66.2(CH 2 ,C-17),72.8(C,C-20),98.3(CH,C-14),114.9(CH,C-9),122.6(C,C-16,CHC(CF 3 ) Cl), 125.8, 128.4, 129.2, 130.5 (CH, C-7, 11, 12, CHC (CF 3 )Cl;C,C-6,8,CHC(CF 3) Cl), 146.0 (C, C-3), 1...

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Abstract

The invention relates to 10-hydroxycamptothecine derivatives and applications thereof and belongs to the field of pesticides. The 10-hydroxycamptothecine is spliced with active sites of a conventional chemical pesticide, namely, a pyrethroid pesticide to obtain a series of pyrethroid-10-hydroxycamptothecine derivatives, so that the pyrethroid-10-hydroxycamptothecine derivatives maintain the original excellent antifeedant activity of the 10-hydroxycamptothecine 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 derivative of 10-hydroxycamptothecin 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 ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/22A01N43/90A01P7/04
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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