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

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

1,2,3,†,* , 1,†
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Received: 4 September 2012; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA 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(10):12140-12150.

Chicago/Turabian Style

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.


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