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J Agric Food Chem

Title:		New analogues of (E)-beta-farnesene with insecticidal activity and binding affinity to aphid odorant-binding proteins
Author(s):		Sun Y; Qiao H; Ling Y; Yang S; Rui C; Pelosi P; Yang X;
Address:		"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"
Journal Title:		J Agric Food Chem
Year:		2011
Volume:		20110222
Issue:		6
Page Number:		2456 - 2461
DOI:		10.1021/jf104712c
ISSN/ISBN:		1520-5118 (Electronic) 0021-8561 (Linking)
Abstract:		"(E)-beta-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)-beta-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)-beta-farnesene. Several derivatives were shown both to bind to A. pisum OBPs with a specificity similar to that of (E)-beta-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)-beta-farnesene endowed with both insecticidal and repellent activity for aphids"
Keywords:		"Animals Aphids/chemistry/*drug effects Insect Proteins/*chemistry Insecticides/chemical synthesis/chemistry/*pharmacology Protein Binding Receptors, Odorant/*chemistry Sesquiterpenes/chemical synthesis/chemistry/*pharmacology Structure-Activity Relationsh;"
Notes:		"MedlineSun, Yufeng Qiao, Huili Ling, Yun Yang, Shaoxiang Rui, Changhui Pelosi, Paolo Yang, Xinling eng Research Support, Non-U.S. Gov't 2011/02/24 J Agric Food Chem. 2011 Mar 23; 59(6):2456-61. doi: 10.1021/jf104712c. Epub 2011 Feb 22"