Identification of Sex Pheromone Components of Blueberry Spanworm Itame argillacearia (Lepidoptera: Geometridae)

Abstract

Blueberry spanworm, Itame argillacearia (Packard), is an important defoliator of lowbush (syn. 'wild') blueberry, Vaccinium angustifolium Aiton, in north-eastern North America. The goal of the present study was to identify the female I. argillacearia sex pheromone, which could be used in traps for monitoring or mass-trapping this pest. Gas chromatography/mass spectrometry (GC/MS) and electroantennogram (EAG) recordings of sex pheromone gland extracts, in combination with chemical synthesis, a Y-tube olfactometer study and field experiments confirmed (2R,3S)-2-ethyl-3-((Z,Z)-tridecadi-2,5-enyl) oxirane (hereafter (Z,Z)-(3R,4S)-3,4-epoxy-6,9-heptadecadiene) and (Z,Z,Z)-3,6,9-heptadecatriene as female-produced sex pheromone components. (Z,Z)-(3R,4S)-3,4-Epoxy-6,9-heptadecadiene elicited a response from male I. argillacearia antennae during EAG recording, and in the Y-tube olfactometer tests males did not discriminate between a live female and (Z,Z)-(3R,4S)-3,4-epoxy-6,9-heptadecadiene. Field-trapping experiments showed that a blend of (Z,Z)-(3R,4S)-3,4-epoxy-6,9-heptadecadiene and (Z,Z,Z)-3,6,9-heptadecatriene was more attractive to male moths than (Z,Z)-(3R,4S)-3,4-epoxy-6,9-heptadecadiene alone.

Identification and characterisation of two general odourant‐binding proteins from the litchi fruit borer, Conopomorpha sinensis Bradley

“…Components such as β ‐caryophyllene could not displace 1‐NPN from 1‐NPN‐ Cs GOBPs in the competitive binding assay, but could attract C. sinensis moths in the Y‐tube assay (data not shown). A feasible explanation for this non‐correspondence is that the Y‐tube olfactometer assay may not be perfectly suited to examining the olfactory response of flying insects . To corroborate this possibility, more thorough investigations of flying insect olfactory orientation behaviour are required, with an improvement in the bioassay set‐up.…”

“…A feasible explanation for this non-correspondence is that the Y-tube olfactometer assay may not be perfectly suited to examining the olfactory response of flying insects. 33,50 To corroborate this possibility, more thorough investigations of flying insect olfactory orientation behaviour are required, with an improvement in the bioassay set-up.…”

“…In order to study C. sinensis moth olfactory orientation behaviour, a Y‐tube olfactometer (one 20 cm arm and two 16 cm branched arms, diameter 1.5 cm) was used in this study that was similar to the dynamic set‐up previously described by Silva et al Air that entered the glass jars was pumped in at a flow rate of 300 mL min −1 , charcoal filtered and humidified with doubly distilled water . Prior to the bioassays with plant odours, a blank test was conducted, and the C. sinensis moth showed no side preference.…”

Semiochemical attractants for the beech leaf‐mining weevil,Orchestes fagi

“…fagi to host compounds and plant material were assayed separately in a Y‐tube olfactometer (1 cm diameter) using methods adapted from De Silva et al. (). Incoming air was charcoal filtered and passed through a two‐channel air delivery system (Analytical Research Systems, Micanopy, FL, USA) to be subsequently split and humidified in two adjoining distilled water bubblers.…”

Synthesis of Functionalized α‐Vinyl Aldehydes from Enaminones

“…The formyl group could also be oxidized selectively by Jones’ reagent to the α‐vinyl acid (Scheme b). Furthermore, the formyl group could selectively undergo olefination with ethyl‐2‐(diethoxyphosphoryl)acetate to give the highly unsaturated ethyl‐( E )‐4‐(2‐oxo‐2‐phenylethyl)‐6,6‐diphenylhexa‐2,5‐dienoate ( 6 ) in 85 % yield (Scheme c) . Highly substituted pyrrole derivatives could be obtained through Paal–Knorr reactions (Scheme d) .…”