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Synthesis and Field Evaluation of the Sex Pheromone Analogues to Soybean Pod Borer Leguminivora glycinivorella
Biorational Pesticide Research & Development Center, Northwest A&F University, Yangling 712100, Shaanxi, China
Shanxi Research Center of Biopesticide Engineering & Technology, Northwest A&F University, Yangling 712100, Shaanxi, China
School of Chemical & Environment Science, Shaanxi University of Technology, Hanzhong 723000, Shaanxi, China
These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 4 September 2012; in revised form: 17 September 2012 / Accepted: 21 September 2012 / Published: 16 October 2012
Abstract: In order to develop efficient lures for soybean pod borer Leguminivora glycinivorella (Matsumura) in China, (E,E)-8,10-dodecadienyl acetate (EE-8,10-12:Ac), the main component of the pheromone of L. glycinivorella, and 12 structurally-related compounds were synthesised in good overall yields, regiospecificities, and stereo-selectivities via coupling reactions catalysed by Li2CuCl4. The effect of different synthetic compounds, alone or in combination with EE-8,10-12:Ac, on numbers of captured L. glycinivorella males was evaluated. EE-8,10-12:Ac, (E)-10-dodecenyl acetate (E-10-12:Ac), (E)-8-dodecenol (E-8-12:OH), tetradecyl acetate (14:Ac), and (Z)-9-tetradecenyl acetate (Z-9-14:Ac) alone displayed different attractiveness to L. glycinivorella males. 14:Ac, E-8-12:OH, E-10-12:Ac, (E,E)-8,10-dodecadienal (EE-8,10-12:Ald), (E)-8-dodecenal (E-8-12:Ald), (E)-10-dodecenal (E-10-12:Ald) and Z-9-14:Ac all showed a synergistic effect to EE-8,10-12:Ac at certain dosages. The binary mixtures of EE-8,10-12:Ac and E-10-12:Ald, Z-9-14:Ac,14:Ac, E-8-12:Ald, EE-8,10-12:Ald, E-8-12:OH, or E-10-12:Ac in suitable ratios give 17.00-, 10.98-, 10.67-, 6.73-, 5.54-, 4.30- and 4.50-fold increases in trap catch, respectively, over the standard pheromone lure, and as novel pheromone blends, demonstrated potential use in pheromone traps to monitor or control L. glycinivorella populations in China.
Keywords: Leguminivora glycinivorella; sex pheromone; synthesis; coupling reaction; attractive activity
MDPI and ACS Style
Hu, D.-H.; He, J.; Zhou, Y.-W.; Feng, J.-T.; Zhang, X. Synthesis and Field Evaluation of the Sex Pheromone Analogues to Soybean Pod Borer Leguminivora glycinivorella. Molecules 2012, 17, 12140-12150.
Hu D-H, He J, Zhou Y-W, Feng J-T, Zhang X. Synthesis and Field Evaluation of the Sex Pheromone Analogues to Soybean Pod Borer Leguminivora glycinivorella. Molecules. 2012; 17(10):12140-12150.
Hu, Dai-Hua; He, Jun; Zhou, Yi-Wan; Feng, Jun-Tao; Zhang, Xing. 2012. "Synthesis and Field Evaluation of the Sex Pheromone Analogues to Soybean Pod Borer Leguminivora glycinivorella." Molecules 17, no. 10: 12140-12150.