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

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, 13&...

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Main Authors:	Yao-Guo Qin, Zhao-Kai Yang, Jia Fan, Xin Jiang, Xin-Ling Yang, Ju-Lian Chen
Format:	Article
Language:	English
Published:	MDPI AG 2020-03-01
Series:	Crystals
Subjects:	synthesis crystal structure nitramide aphicidal activity antifungal activity
Online Access:	https://www.mdpi.com/2073-4352/10/4/245

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spelling	doaj-5c46a160498c44fc8a5ed6655e32d3b32020-11-25T00:44:43ZengMDPI AGCrystals2073-43522020-03-0110424510.3390/cryst10040245cryst10040245Synthesis, Crystal Structure and Bioactivities of <i>N</i>-(5-(4-chlorobenzyl)-1,3,5-Triazinan-2-Ylidene)NitramideYao-Guo Qin0Zhao-Kai Yang1Jia Fan2Xin Jiang3Xin-Ling Yang4Ju-Lian Chen5State Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, ChinaDepartment of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, ChinaState Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, ChinaState Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, ChinaDepartment of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, ChinaState Key Laboratory for Biology of Plant Diseases and Insect Pests, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, ChinaThe 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.https://www.mdpi.com/2073-4352/10/4/245synthesiscrystal structurenitramideaphicidal activityantifungal activity
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Yao-Guo Qin Zhao-Kai Yang Jia Fan Xin Jiang Xin-Ling Yang Ju-Lian Chen
spellingShingle	Yao-Guo Qin Zhao-Kai Yang Jia Fan Xin Jiang Xin-Ling Yang Ju-Lian Chen Synthesis, Crystal Structure and Bioactivities of <i>N</i>-(5-(4-chlorobenzyl)-1,3,5-Triazinan-2-Ylidene)Nitramide Crystals synthesis crystal structure nitramide aphicidal activity antifungal activity
author_facet	Yao-Guo Qin Zhao-Kai Yang Jia Fan Xin Jiang Xin-Ling Yang Ju-Lian Chen
author_sort	Yao-Guo Qin
title	Synthesis, Crystal Structure and Bioactivities of <i>N</i>-(5-(4-chlorobenzyl)-1,3,5-Triazinan-2-Ylidene)Nitramide
title_short	Synthesis, Crystal Structure and Bioactivities of <i>N</i>-(5-(4-chlorobenzyl)-1,3,5-Triazinan-2-Ylidene)Nitramide
title_full	Synthesis, Crystal Structure and Bioactivities of <i>N</i>-(5-(4-chlorobenzyl)-1,3,5-Triazinan-2-Ylidene)Nitramide
title_fullStr	Synthesis, Crystal Structure and Bioactivities of <i>N</i>-(5-(4-chlorobenzyl)-1,3,5-Triazinan-2-Ylidene)Nitramide
title_full_unstemmed	Synthesis, Crystal Structure and Bioactivities of <i>N</i>-(5-(4-chlorobenzyl)-1,3,5-Triazinan-2-Ylidene)Nitramide
title_sort	synthesis, crystal structure and bioactivities of <i>n</i>-(5-(4-chlorobenzyl)-1,3,5-triazinan-2-ylidene)nitramide
publisher	MDPI AG
series	Crystals
issn	2073-4352
publishDate	2020-03-01
description	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.
topic	synthesis crystal structure nitramide aphicidal activity antifungal activity
url	https://www.mdpi.com/2073-4352/10/4/245
work_keys_str_mv	AT yaoguoqin synthesiscrystalstructureandbioactivitiesofini54chlorobenzyl135triazinan2ylidenenitramide AT zhaokaiyang synthesiscrystalstructureandbioactivitiesofini54chlorobenzyl135triazinan2ylidenenitramide AT jiafan synthesiscrystalstructureandbioactivitiesofini54chlorobenzyl135triazinan2ylidenenitramide AT xinjiang synthesiscrystalstructureandbioactivitiesofini54chlorobenzyl135triazinan2ylidenenitramide AT xinlingyang synthesiscrystalstructureandbioactivitiesofini54chlorobenzyl135triazinan2ylidenenitramide AT julianchen synthesiscrystalstructureandbioactivitiesofini54chlorobenzyl135triazinan2ylidenenitramide
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Synthesis, Crystal Structure and Bioactivities of <i>N</i>-(5-(4-chlorobenzyl)-1,3,5-Triazinan-2-Ylidene)Nitramide

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