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European corn borer sex pheromone : Structure-activity relationships.

M Schwarz1, J A Klun, G L Fritz

  • 1Insect Chemical Ecology Laboratory Agricultural Research Service, USDA, 20705, Beltsville, Maryland.

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|November 26, 2013
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Structural modifications of European corn borer pheromones reveal specific requirements for male moth attraction. Different analogs showed varied activity, highlighting distinct receptor mechanisms between European corn borer strains and the redbanded leafroller.

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Area of Science:

  • Chemical Ecology
  • Insect Behavior
  • Molecular Biology

Background:

  • The European corn borer (Ostrinia nubilalis) uses specific isomers of 11-tetradecen-1-ol acetate as sex pheromones.
  • Male moths exhibit behavioral responses to pheromones at different activity levels: short-range stimulation, flight tunnel activation, and field response.

Purpose of the Study:

  • To investigate the biological activity of modified pheromone analogs in European corn borer.
  • To determine the structural requirements for pheromonal activity at different behavioral response levels.
  • To compare the pheromone perception mechanisms between European corn borer and the redbanded leafroller (Argyrotaenia velutinana).

Main Methods:

  • Synthesis and testing of novel analogs of (Z)- and (E)-11-tetradecen-1-ol acetate with modifications in the terminal alkyl chain.
  • Evaluation of analog activity in flight tunnel bioassays using different pheromonal types of O. nubilalis.
  • Testing of active analogs against Argyrotaenia velutinana to assess cross-species receptor differences.

Main Results:

  • Flight tunnel activity required specific chain lengths (13-14 carbons) and limited branching (methyl or cyclopropyl at C13).
  • Three new analogs, including (Z)-13-methyl-11-tetradecen-1-ol acetate and (Z)-12-cyclopropyl-11-dodecen-1-ol acetate, showed flight tunnel activity.
  • The cyclopropyl analog was highly active against the ZZ pheromone type, while its E isomer acted as an antagonist in the EE type, suggesting strain-specific receptor differences.
  • Argyrotaenia velutinana exhibited different pheromone reception, with only marginal response to one analog, indicating distinct acceptor systems.

Conclusions:

  • Pheromone reception in O. nubilalis involves increasingly restrictive structural requirements for different behavioral responses.
  • Structural variations in pheromone analogs can lead to differential activity and even antagonistic effects, underscoring receptor specificity.
  • Despite using similar pheromone components, O. nubilalis and A. velutinana possess distinct pheromone perception mechanisms.