Sex pheromone of the soybean pod borer, Leguminivora glycinivorella (Lepidoptera: Tortricidae): Identification and field evaluation

Abstract

With reference to the data of synthetic standards, GC-EAD and GC-MS analyses of a pheromone gland extract of the soybean pod borer, Leguminivora glycinivorella (Lepidoptera: Tortricidae), resulted in three acetates [dodecyl acetate, (8E,10E)-8,10-dodecadienyl acetate (E8,E10-12:OAc), and its (8E,10Z)-isomer] at a ratio of 10 : 100 : 2.5 as a candidate of the pheromone. While the contents in the glands were low and even the titer of the major pheromonal component was ca. 0.5 ng/female, the positions of the two double bonds were confirmed by a mass spectrum of the adduct with 4-methyl-1,2,4-triazoline-3,5-dione. In a soybean field, synthetic E8,E10-12:OAc successfully attracted male moths of L. glycinivorella, and highly selective attraction was observed for E8,E10-12:OAc among the geometrical isomers of the 8,10-diene. Neither of the two minor components showed a synergistic effect on field attraction by E8,E10-12:OAc, and their roles were unclear. A binary lure of E8,E10-12:OAc and (E)-8-dodecenyl acetate (E8-12:OAc) was necessary to attract the male moths of Matsumuraeses falcana, the soybean pod worm, but E8-12:OAc strongly inhibited the attraction of L. glycinivorella by E8,E10-12:OAc, indicating that E8-12:OAc secreted by M. falcana is one of the most important factors in the reproductive isolation of these two species.

Up the Hill: Selective Double‐Bond Isomerization of Terminal 1,3‐Dienes towards Z‐1,3‐Dienes or 2Z,4E‐Dienes

“…Of note, some long-chained 2Z,4E-configured dienes have been found in nature, mostly as pheromones or as part of more complex natural products, such as product 6 a or a compound related to product 6 g. [9] Accordingly, applications of this new method in natural product synthesis can be envisaged.…”

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

“…The effect on catch when other synthetic compounds were combined with EE -8,10-12:Ac varied with the compound and dose. In 2006, it has been reported that E- 8-12:Ac strongly inhibited the attractiveness of EE- 8,10-12:Ac to L. glycinivorella in Japan [ 1 ]. When tested as a single compound, E -8-12:Ac was not attractive to L. glycinivorella males ( Table 1 ).…”

“…Compound 12:Ac has been detected in a gland extract of L. glycinivorella pheromone, and the GC-EAD showed that it was antennally active [ 1 ]. When tested as a single compound, 12:Ac alone was not attractive to L. glycinivorella males ( Table 1 ), and significantly decreased mean catch when added to traps baited with EE- 8,10-12:Ac at doses of 0.01 and 0.5 mg per septum ( Figure 3 ).…”

“…Larvae feed mainly on the pod hulls, especially of young beans, severely reducing crop yield and quality. ( E,E )-8,10-Dodecadienyl acetate ( EE- 8,10-12:Ac) is the main sex pheromone of L. glycinivorella [ 1 ]. 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 PdCl 2 (dppf), CH 2 Cl 2 and Cs 2 CO 3 [ 2 ].…”

Suitability of Chinese oak silkworm eggs for the multigenerational rearing of the parasitoid Trichogramma leucaniae

“…However, the somewhat conservative polices and legal obstacles to transgenic crops in many countries limited the applications of this procedure in soybean [13]. Similarly, certain sex pheromones have also been chemically identified and used to monitor population dynamics and control SPB by mating disruption [14]. The use of resistant cultivars is also an effective way for reducing insect pest damage in combination with other non-chemical control measures [15].…”