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Molecules 2016, 21(7), 825; doi:10.3390/molecules21070825

Novel (E)-β-Farnesene Analogues Containing 2-Nitroiminohexahydro-1,3,5-triazine: Synthesis and Biological Activity Evaluation

1
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
2
Department of Entomology, College of Plant Protection, China Agricultural University, Beijing 100193, China
*
Author to whom correspondence should be addressed.
Academic Editor: Wei-Zhu Zhong
Received: 15 March 2016 / Revised: 18 June 2016 / Accepted: 20 June 2016 / Published: 24 June 2016
(This article belongs to the Special Issue Drug Design and Discovery: Principles and Applications)
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Abstract

In order to discover novel eco-friendly compounds with good activity for aphid control, (E)-β-farnesene (EβF), 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 EβF, a series of novel EβF 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 1H-NMR, 13C-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 EβF analogues. View Full-Text
Keywords: (E)-β-farnesene analogues; 2-nitroiminohexahydro-1,3,5-triazine; synthesis; bioactivity; structure-activity relationship (E)-β-farnesene analogues; 2-nitroiminohexahydro-1,3,5-triazine; synthesis; bioactivity; structure-activity relationship
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Qin, Y.; Zhang, J.; Song, D.; Duan, H.; Li, W.; Yang, X. Novel (E)-β-Farnesene Analogues Containing 2-Nitroiminohexahydro-1,3,5-triazine: Synthesis and Biological Activity Evaluation. Molecules 2016, 21, 825.

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