Synthesis, Crystal Structure and Bioactivities of N-(5-(4-chlorobenzyl)-1,3,5-Triazinan-2-Ylidene)Nitramide

Yao-Guo Qin,Xin Jiang,Zhao-Kai Yang,Ju-Lian Chen,Xin-Ling Yang,Jia Fan

doi:10.3390/cryst10040245

Abstract

The compound N-(5-(4-chlorobenzyl)-1,3,5-triazinan-2-ylidene)nitramide (C10H12ClN5O2, M = 269.70) was synthesized and structurally confirmed by 1H NMR, 13C NMR, HRMS and single-crystal x-ray diffraction. The crystal belongs to the monoclinic system with space group P21/c. The title compound consisted of a benzene ring and a 1,3,5-triazine ring. All carbon atoms in the benzene ring were nearly coplanar with a dihedral (C6–C5–C10 and C7–C8–C9) angle of 1.71°and all non-hydrogen atoms of the 1,3,5-triazine ring were not planar, but exhibited a half-chair conformation. The crystal structure was stabilized by a strong intramolecular hydrogen bonding interaction N(3)–H(3)···O(2) and three intermolecular hydrogen bonding interactions, N(2)–H(2)···O(1), N(2)–H(2)···N(4) and N(3)–H(3)···Cl(1). The preliminary bioassay showed that the title compound showed not only aphicidal activity against Sitobion miscanthi (inhibition rate: 74.1%) and Schizaphis graminum (77.5%), but also antifungal activities against Pythium aphanidermatum (62.0%). These results provide valuable guidelines for the design and synthesis of novel aphid control agents and fungicides.

Highlights

Substituted triazine compounds have attracted more and more attention in recent years for their use as medicines [1,2,3] and agrochemicals [4,5,6], such as adenosine A antagonists, anticonvulsants, antimicrobials, anticancer agents, bactericides, herbicides and insecticides
As part of our ongoing work in exploring triazine active chemical structures, we noticed that a type of 2-nitroimino-hexahydro-1,3,5-triazine (NHT) derivatives displayed biological activity against the apterous adult aphids of M. persicae [21,22] and Acyrthosiphon pisum [23]
In the view of these facts and in order to further search for NHT derivatives with high bioactivity and broad-spectrum, the titled compound N-(5-(4-chlorobenzyl)-1,3,5-triazinan-2-ylidene)nitramide (1), was designed by introducing benzyl group active substructure into NHT scaffold

Summary

Introduction

Substituted triazine compounds have attracted more and more attention in recent years for their use as medicines [1,2,3] and agrochemicals [4,5,6], such as adenosine A antagonists, anticonvulsants, antimicrobials, anticancer agents, bactericides, herbicides and insecticides. Among these triazines, hexahydro-1,3,5-triazine, is endowed with simple structure and very important pharmaceutical activities, such as insecticidal [7], antifungal [8], herbicidal [9] and antiviral [10] activities.

Methods

Results

Conclusion