Efficient Synthesis and Bioactivity of Novel Triazole Derivatives.

Boyang Hu,Wenting Zhao,Jianzhuang Zhao,Chen Xu,Zili Chen,Hanqing Zhao

doi:10.3390/molecules23040709

Boyang Hu, Wenting Zhao + Show 4 more

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https://doi.org/10.3390/molecules23040709

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Abstract

Triazole pesticides are organic nitrogen-containing heterocyclic compounds, which contain 1,2,3-triazole ring. In order to develop potential glucosamine-6-phosphate synthase (GlmS) inhibitor fungicides, forty compounds of triazole derivatives were synthesized in an efficient way, thirty nine of them were new compounds. The structures of all the compounds were confirmed by high resolution mass spectrometer (HRMS), 1H-NMR and 13C-NMR. The fungicidal activities results based on means of mycelium growth rate method indicated that some of the compounds exhibited good fungicidal activities against P. CapasiciLeonian, Sclerotinia sclerotiorum (Lib.) de Bary, Pyricularia oryzae Cav. and Fusarium oxysporum Schl. F.sp. vasinfectum (Atk.) Snyd. & Hans. at the concentration of 50 µg/mL, especially the inhibitory rates of compounds 1-d and 1-f were over 80%. At the same time, the preliminary studies based on the Elson-Morgan method indicated that the compounds exhibited some inhibitory activity toward glucosamine-6-phosphate synthase (GlmS). These compounds will be further studied as potential antifungal lead compounds. The structure-activity relationships (SAR) were discussed in terms of the effects of the substituents on both the benzene and the sugar ring.

Highlights

Carbohydrates play an important role in the field of pesticide investigation, and many natural carbohydrate products used as pesticides have shown great vitality [1]
The new fungicides, which were developed based on carbohydrate compounds, have advantages of safety, high efficiency, low residue and not easy to generate insecticide resistance [4,5], ensuring the high yield of vegetables and other agricultural products [6], and solve the problem of pesticide residues
Optical rotations were recorded using a Perkin-Elmer 241 polarimeter (Perkin-Elmer, Waltham, MA, USA). 1 H-NMR (400 MHz) and 13 C-NMR (100 MHz) spectra was recorded in CDCl3, Meth-d4 or DMSO-d6 with a Bruker DPX400 spectrometer (Brook (Beijing) science and Technology Co., Ltd., Beijing, China), using Tetramethyl silane (TMS) as internal standard; Mass spectra were obtained with Agilent 1100 series LC/MSD mass spectrometer (Agilent Technologies Inc., Beijing, China)

Summary

Introduction

Carbohydrates play an important role in the field of pesticide investigation, and many natural carbohydrate products used as pesticides have shown great vitality [1]. Triazole pesticides are the most widely used variety of fungicides in agricultural production, which are mainly divided into fungicides, herbicides, pesticides and plant growth regulators [7]. In addition to a strong internal fungicidal activity, triazole compounds have a regulatory role in the growth of plant [12], herbicidal [13], insecticidal [14] and antifungal [15,16]. Because of these multiple effect of the triazole structure, the research of these compounds have been in the ascendant so far. In order to obtain more efficient derivatives, the chemical structure modification of Molecules 2018, 23, 709; doi:10.3390/molecules23040709 www.mdpi.com/journal/molecules

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