title: New analogues of (E)-β-farnesene with insecticidal activity and binding affinity to aphid odorant-binding proteins.
abstract: (E)-β-farnesene is a strong and efficient alarm pheromone in most aphid species. However, applications in agriculture are prevented by its relatively high volatility, its susceptibility to oxidation and its complex and expensive synthesis. To develop novel compounds for aphid control, we have designed and synthesized analogues of (E)-β-farnesene, containing a pyrazole moiety present in several insecticides. Their structures have been confirmed by 1H NMR, elemental analysis, high-resolution mass spectroscopy and IR. Binding activities to three odorant-binding proteins (OBPs) of the pea aphid Acythosiphon pisum have been evaluated and correlated with their structures with reference to (E)-β-farnesene. Several derivatives were shown both to bind to A. pisum OBPs with a specificity similar to that of (E)-β-farnesene and to have aphicidal activity comparable to that of thiacloprid, a commercial insecticide. The compounds synthesized in this work represent new potential agents for aphid population control and provide guidelines to design analogues of (E)-β-farnesene endowed with both insecticidal and repellent activity for aphids.
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Beijing 100193, People's Republic of China.
authors.forename: Yufeng
authors.initials: Y
authors.lastname: Sun
authors.forename: Huili
authors.initials: H
authors.lastname: Qiao
authors.forename: Yun
authors.initials: Y
authors.lastname: Ling
authors.forename: Shaoxiang
authors.initials: S
authors.lastname: Yang
authors.forename: Changhui
authors.initials: C
authors.lastname: Rui
authors.forename: Paolo
authors.initials: P
authors.lastname: Pelosi
authors.forename: Xinling
authors.initials: X
authors.lastname: Yang
mesh_terms: D000818:Animals; D001042:Aphids / Q000737:chemistry / Q000187:drug effects*; D019476:Insect Proteins / Q000737:chemistry*; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011485:Protein Binding; D018035:Receptors, Odorant / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D019476:Insect Proteins; D007306:Insecticides; D018035:Receptors, Odorant; D012717:Sesquiterpenes; C045648:odorant-binding protein; C062671:beta-farnesene