title: Novel (E)-β-Farnesene Analogues Containing 2-Nitroiminohexahydro-1,3,5-triazine: Synthesis and Biological Activity Evaluation.
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, (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 EβF analogues.
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. qyg@cau.edu.cn.
authors.forename: Yaoguo
authors.initials: Y
authors.lastname: Qin
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. jpzhang@cau.edu.cn.
authors.forename: Jingpeng
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Department of Entomology, College of Plant Protection, China Agricultural University, Beijing 100193, China. songdl@cau.edu.cn.
authors.forename: Dunlun
authors.initials: D
authors.lastname: Song
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. hxduan@cau.edu.cn.
authors.forename: Hongxia
authors.initials: H
authors.lastname: Duan
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. oliverlwh@cau.edu.cn.
authors.forename: Wenhao
authors.initials: W
authors.lastname: Li
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. yangxl@cau.edu.cn.
authors.forename: Xinling
authors.initials: X
authors.lastname: Yang
mesh_terms: D000818:Animals; D001042:Aphids / Q000187:drug effects; D015195:Drug Design; D007302:Insect Repellents / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014227:Triazines / Q000737:chemistry*
chemical_list: D007302:Insect Repellents; D012717:Sesquiterpenes; D014227:Triazines; C062671:beta-farnesene
keywords: (E)-β-farnesene analogues; 2-nitroiminohexahydro-1,3,5-triazine; bioactivity; structure-activity relationship; synthesis