1. Synthesis, Crystal Structure and Bioactivities of N-(5-(4-chlorobenzyl)-1,3,5-Triazinan-2-Ylidene)Nitramide
- Author
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Ju-Lian Chen, Xin Jiang, Zhaokai Yang, Jia Fan, Yaoguo Qin, and Xin-Ling Yang
- Subjects
crystal structure ,synthesis ,General Chemical Engineering ,Crystal structure ,Nitramide ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Medicinal chemistry ,Inorganic Chemistry ,chemistry.chemical_compound ,lcsh:QD901-999 ,General Materials Science ,010405 organic chemistry ,Hydrogen bond ,antifungal activity ,nitramide ,aphicidal activity ,Carbon-13 NMR ,Condensed Matter Physics ,0104 chemical sciences ,chemistry ,Intramolecular force ,Proton NMR ,lcsh:Crystallography ,Monoclinic crystal system - 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&ndash, C5&ndash, C10 and C7&ndash, C8&ndash, 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)&ndash, H(3)·, ·, O(2) and three intermolecular hydrogen bonding interactions, N(2)&ndash, H(2)·, O(1), N(2)&ndash, N(4) and N(3)&ndash, 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.
- Published
- 2020
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