Synthesis and Larvicidal Activity against Culex pipiens pallens of New Triazole Derivatives of Phrymarolin from Phryma leptostachya L.

Ji-Wen Zhang,Zhao-Nong Hu,Zhan Hu,Peng Gao,Jun-Ru Wang,Wen-Jun Wu

doi:10.3390/ijms141224064

Ji-Wen Zhang, Zhao-Nong Hu + Show 4 more

Open Access

https://doi.org/10.3390/ijms141224064

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Abstract

Twelve new triazole derivatives of Phrymarolin were prepared from Phrymarolin I and the structures of all the derivatives were fully characterized by 1H-NMR, 13C-NMR and MS spectral data analyses. Larvicidal activities against 4rd instar larvae of Culex pipiens pallens of these Phrymarolin analogues were assayed. Although the triazole derivatives of Phrymarolin showed certain larvicidal activity, they showed lower activity than Phrymarolin I. The typical non-natural groups triazole substituents reduced the larvicidal activity of Phrymarolin derivatives.

Highlights

Mosquitoes are significant public health pests for humans and domesticated animals, responsible for spreading serious vector-borne diseases like malaria, filariasis, epidemic encephalitis, yellow fever, dengue, etc
As part of an ongoing effort to identify potential pesticide molecules derived from natural products it was shown that lignans including Haedoxane A, Phrymarolin B and Phrymarolins I are the main active components of P. leptostachya L. (Figure 1) [8,9,10]
In our previous study [11,12,13], we found that some of the C-11 ether derivatives and dehydroxy Phrymarolin showed much higher activity than Phrymarolins I

Summary

Introduction

Mosquitoes are significant public health pests for humans and domesticated animals, responsible for spreading serious vector-borne diseases like malaria, filariasis, epidemic encephalitis, yellow fever, dengue, etc. Investigation of natural products with insecticidal activities from plant may lead to find novel insecticides as the prominent examples of pyrethroids. As part of an ongoing effort to identify potential pesticide molecules derived from natural products it was shown that lignans including Haedoxane A, Phrymarolin B and Phrymarolins I are the main active components of P. leptostachya L. The synthesis and larvicidal activity against Culex pipiens pallens that is the most common mosquito in houses of Northern China and the primary vector of filariasis and epidemic encephalitis of novel triazole derivatives of Phrymarolin I will be described.

Results and Discussion

General

Synthesis of Derivatives of Phrymarolins I

Bioassay for Larvicidal Activities

Conclusions