Synthesis, Crystal Structure and Bioactivities of <i>N</i>-(5-(4-chlorobenzyl)-1,3,5-Triazinan-2-Ylidene)Nitramide
oleh: Yao-Guo Qin, Zhao-Kai Yang, Jia Fan, Xin Jiang, Xin-Ling Yang, Ju-Lian Chen
| Format: | Article |
|---|---|
| Diterbitkan: | MDPI AG 2020-03-01 |
Deskripsi
The compound <i>N</i>-(5-(4-chlorobenzyl)-1,3,5-triazinan-2-ylidene)nitramide (C<sub>10</sub>H<sub>12</sub>ClN<sub>5</sub>O<sub>2</sub>, M = 269.70) was synthesized and structurally confirmed by <sup>1</sup>H NMR, <sup>13</sup>C NMR, HRMS and single-crystal x-ray diffraction. The crystal belongs to the monoclinic system with space group <i>P</i>2<sub>1</sub>/<i>c</i>. 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 <i>Sitobion miscanthi</i> (inhibition rate: 74.1%) and <i>Schizaphis graminum</i> (77.5%), but also antifungal activities against <i>Pythium aphanidermatum</i> (62.0%). These results provide valuable guidelines for the design and synthesis of novel aphid control agents and fungicides.