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Molecules 2012, 17(10), 12140-12150; doi:10.3390/molecules171012140

Synthesis and Field Evaluation of the Sex Pheromone Analogues to Soybean Pod Borer Leguminivora glycinivorella

1,2,3,†,* , 1,†
,
1
,
1
and
1,*
1
Biorational Pesticide Research & Development Center, Northwest A&F University, Yangling 712100, Shaanxi, China
2
Shanxi Research Center of Biopesticide Engineering & Technology, Northwest A&F University, Yangling 712100, Shaanxi, China
3
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 / Revised: 17 September 2012 / Accepted: 21 September 2012 / Published: 16 October 2012
(This article belongs to the Section Organic Synthesis)
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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 Leguminivora glycinivorella; sex pheromone; synthesis; coupling reaction; attractive activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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