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.

Highlights

  • Leguminivora glycinivorella is one of the most destructive soybean pests in North China

  • Our goal is to develop efficient lures for monitoring and controlling soybean pod borer population in China

  • Our results show that E-8-12:Ac is one of the inhibitors of the sex pheromone EE-8,10-12:Ac to L. glycinivorella in Heilongjiang Province, China

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Summary

Introduction

Leguminivora glycinivorella is one of the most destructive soybean pests in North China. In 2008 Wu reported the synthesis of EE-8,10-12:Ac by the use of Suzuki-Miyaura cross-coupling reaction between potassium (E)-1-propenyl trifluoroborate and (E)-9-iodo-1-(2-tetrahydropyranyloxy)8-nonene in the presence of PdCl2(dppf), CH2Cl2 and Cs2CO3 [2]. This method suffers from high cost and difficulties associated with industrial scale-up. A strong attraction to male moths by a mixture of EE-8,10-12:Ac and E10-12:Ac in a ratio of 2:5 was observed. This reported pheromone lure does not work well in Heilongjiang Province, China. This discrepancy may attribute to the different habitats of L. glycinivorella in Heilongjiang and

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