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

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.

Transcriptomic and proteomic analyses of the mechanisms of overwintering diapause in soybean pod borer (Leguminivora glycinivorella)

“…However, the larvae within soybean pods under a closed canopy are not exposed to the applied insecticides. 2,5,7,8 Therefore, systemic pesticides are used to control L. glycinivorella. However, systemic insecticides have insidious effects on bee pollinators and the environment.…”

“…Insecticides have been used to control L. glycinivorella infestations over the past four decades. However, the larvae within soybean pods under a closed canopy are not exposed to the applied insecticides 2,5,7,8 . Therefore, systemic pesticides are used to control L. glycinivorella .…”

Monobromination of α,ω‐Diols: Highly Efficient Preparation of Synthetic Intermediates

“…This reaction between diols and hydrobromic acid (HBr) has been described as taking place in solvents with boiling points ranging from 80 to 110 °C, under reflux, using the Dean‐Stark apparatus to collect the water formed, although removal of water seems to be prejudicial to the monobromination, increasing dibromide formation . Benzene and toluene generally are the solvents of choice, this type of assay, however, is reportedly feasible in hexane as well . There are precedents of monobrominations of α,ω ‐diols conducted without the water collecting apparatus, but, even in these cases, reaction times were as high as the ones where the water was removed, needing up to 24 h to form the desired product with appreciable yields .…”

Phenotypic Plasticity of HSP70s Gene Expression during Diapause: Signs of Evolutionary Responses to Cold Stress among Soybean Pod Borer Populations (Leguminivora glycinivorella) in Northeast of China

“…Only one generation of L. glycinivorella lives in the northeast region of China, which is the main soybean production region, and its diapause stage lasts from October to July [35] , [36] . L. glycinivorella can cause severe losses in soybean yield and quality; the loss rate is from 10% to 30% in a general year and up to 50% for more severe situations in a typical year [37] , [38] . To date, research concerning L. glycinivorella has primarily focused on environmental ecology and physiology and has not focused on the genetic regulation of the diapause stage.…”