Communication Disruption of Guava Moth (Coscinoptycha improbana) Using a Pheromone Analog Based on Chain Length

Abstract

The guava moth, Coscinoptycha improbana, an Australian species that infests fruit crops in commercial and home orchards, was first detected in New Zealand in 1997. A four-component pheromone blend was identified but is not yet commercially available. Using single sensillum recordings from male antennae, we established that the same olfactory receptor neurons responded to two guava moth sex pheromone components, (Z)-11-octadecen-8-one and (Z)-12-nonadecen-9-one, and to a chain length analog, (Z)-13-eicosen-10-one, the sex pheromone of the related peach fruit moth, Carposina sasakii. We then field tested whether this non-specificity of the olfactory neurons might enable disruption of sexual communication by the commercially available analog, using male catch to synthetic lures in traps in single-tree, nine-tree and 2-ha plots. A disruptive pheromone analog, based on chain length, is reported for the first time. Trap catches for guava moth were disrupted by three polyethylene tubing dispensers releasing the analog in single-tree plots (86% disruption of control catches) and in a plots of nine trees (99% disruption). Where peach fruit moth pheromone dispensers were deployed at a density of 1000/ha in two 2-ha areas, pheromone traps for guava moth were completely disrupted for an extended period (up to 470 days in peri-urban gardens in Mangonui and 422 days in macadamia nut orchards in Kerikeri). In contrast, traps in untreated areas over 100 m away caught 302.8 ± 128.1 moths/trap in Mangonui and 327.5 ± 78.5 moths/ trap in Kerikeri. The longer chain length in the pheromone analog has greater longevity than the natural pheromone due to its lower volatility. Chain length analogs may warrant further investigation for mating disruption in Lepidoptera, and screening using single-sensillum recording is recommended.

Structural and biochemical evaluation of Ceratitiscapitata odorant‐binding protein 22 affinity for odorants involved in intersex communication

“…The analysis of the unusual features of the CcapOBP22 binding pocket will also be useful for future structure-based design, for in silico ligand identification as well as optimization of chemical scaffolds that can be exploited as new tools to interfere with medfly olfaction (Carey and Carlson, 2011;Suckling et al, 2013;Pelosi et al, 2014), or to improve the efficacy of trapping systems (Tan et al, 2014). Given its sequence divergence from other OBPs characterized using structural biology, the molecular structure of CcapOBP22 will be a useful starting point to investigate the molecular architecture of the numerous as-yet-uncharacterized OBP molecules from C. capitata and from other insects.…”

“…Given its sequence divergence from other OBPs characterized using structural biology, the molecular structure of CcapOBP22 will be a useful starting point to investigate the molecular architecture of the numerous as-yet-uncharacterized OBP molecules from C. capitata and from other insects. The analysis of the unusual features of the CcapOBP22 binding pocket will also be useful for future structure-based design, for in silico ligand identification as well as optimization of chemical scaffolds that can be exploited as new tools to interfere with medfly olfaction (Carey and Carlson, 2011;Suckling et al, 2013;Pelosi et al, 2014), or to improve the efficacy of trapping systems (Tan et al, 2014).…”

Synthesis and Electrophysiological Testing of Carbonyl Pheromone Analogues for Carposinid Moths

“…9 For the carposinid moths, Suckling et al investigated chain length variants using the peach fruit moth pheromone to disrupt guava moth. 10 More recently, Twidle et al have shown that the ester analogue (Z)-heptyl undec-4-enoate has an inhibitory effect on raspberry bud moth, 11 similar to that of the formate analogues of Type I aldehyde pheromones. 12 The aim of this work was to build on that knowledge and investigate changes directly to the carbonyl group of (7Z)-alken-11-ones of the carposinids, focusing on (Z)-nonadec-12-en-9-one (1) (or as it is historically known, (7Z)-nonadecen-11-one) which is common to the three known carposinid pheromone blends.…”

“…Rigorous degassing of the solvents reduced the unwanted disulfide formation, allowing the target compound (Z)-dec-3-enyl(octyl)sulfane ( 9) to be produced with a satisfactory yield of 54%. The final step of the synthesis was the oxidation of the thioether (9) to the target sulfoxide (Z)-1-(octylsulfinyl)-dec-3-ene (10). This was achieved using the TeO 2 −H 2 O 2 system of Kwan et al, 15 giving the sulfoxide (10) in 87% yield.…”

“…The combined organic extracts were then dried (MgSO 4 ) and the solvent removed under vacuum. The crude thioether was then purified by column chromatography (silica gel, hexane) to give the title product (Z)-dec-3enyl(octyl)sulfane (9) (Z)-1-(Octylsulfinyl)-dec-3-ene (10). To a solution of thioether (9) (284 mg, 1.00 mmol), TeO 2 (16 mg, 0.10 mmol), and HCl (cat.)…”