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Molecules

Title:		"Novel (E)-beta-Farnesene Analogues Containing 2-Nitroiminohexahydro-1,3,5-triazine: Synthesis and Biological Activity Evaluation"
Author(s):		Qin Y; Zhang J; Song D; Duan H; Li W; Yang X;
Address:		"Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. qyg@cau.edu.cn. Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. jpzhang@cau.edu.cn. Department of Entomology, College of Plant Protection, China Agricultural University, Beijing 100193, China. songdl@cau.edu.cn. Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. hxduan@cau.edu.cn. Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. oliverlwh@cau.edu.cn. Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. yangxl@cau.edu.cn"
Journal Title:		Molecules
Year:		2016
Volume:		20160624
Issue:		7
Page Number:		-
DOI:		10.3390/molecules21070825
ISSN/ISBN:		1420-3049 (Electronic) 1420-3049 (Linking)
Abstract:		"In order to discover novel eco-friendly compounds with good activity for aphid control, (E)-beta-farnesene (EbetaF), the main component of the aphid alarm pheromone, was chosen as the lead compound. By introducing a 2-nitroimino-hexahydro-1,3,5-triazine moiety (abbreviated NHT) to replace the unstable conjugated double bond system of EbetaF, a series of novel EbetaF analogues containing the NHT moiety were synthesized via the reaction of substituted NHT rings with (E)-1-chloro-3,7-dimethylocta-2,6-diene. All the compounds were characterized by (1)H-NMR, (13)C-NMR, IR, and high resolution mass spectroscopy (HRMS). The bioassay results showed that all the analogues displayed different repellent and aphicidal activities against green peach aphid (Myzus persicae). Particularly, the analogue 4r exhibited obvious repellent activity (repellent proportion: 78.43%) and similar aphicidal activity against M. persicae (mortality: 82.05%) as the commercial compound pymetrozine (80.07%). A preliminary structure-activity relationship (SAR) study was also performed, which offered valuable clues for the design of further new EbetaF analogues"
Keywords:		"Animals Aphids/drug effects Drug Design Insect Repellents/chemistry/pharmacology Models, Molecular Molecular Structure Sesquiterpenes/*chemical synthesis/chemistry/*pharmacology Structure-Activity Relationship Triazines/*chemistry (E)-beta-farnesene analo;"
Notes:		"MedlineQin, Yaoguo Zhang, Jingpeng Song, Dunlun Duan, Hongxia Li, Wenhao Yang, Xinling eng Switzerland 2016/06/28 Molecules. 2016 Jun 24; 21(7):825. doi: 10.3390/molecules21070825"