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Journal of Chemical Ecology

, Volume 15, Issue 2, pp 685–695 | Cite as

Structure-activity studies on aggregation pheromone components ofPityogenes chalcographus (Coleoptera: Scolytidae)

All stereoisomers of chalcogran and methyl 2,4-decadienoate
  • John A. Byers
  • Hans-Erik Högberg
  • C. Rikard Unelius
  • Göran Birgersson
  • Jan Löfqvist
Article

Abstract

Syntheses of all four Stereoisomers (2S,5S; 2S,5R;2R,5R; and2R,5S) of chalcogran, a major component of the aggregation pheromone ofPityogenes chalcographus, and of all four isomers (2Z,4Z; 2Z,4E; 2E,4E; and 2E,4Z) of methyl 2,4-decadienoate (MD), the second major pheromone component, are briefly described. Attraction responses of walking beetles of both sexes were tested to mixtures of the synergistic pheromone components or analogs. These bioassays showed that theE,Z isomer of MD is the most active when tested with chalcogran. When tested with (E,Z)-MD, (2S,5R)-chalcogran was the most active stereoisomer, while 2R,5R and 2R,5S isomers had intermediate activities, and the 2S,5S isomer was inactive. There was no evidence that the relatively less active Stereoisomers of chalcogran inhibited or promoted attraction to (2S,5R)-chalcogran with (E,Z)-MD. Male beetles only produce the activeE,Z isomer of MD (inactive alone) and their hindguts contain the most active (2S,5R)- and least active (2S,5S)-chalcogran. A mixture of all MD isomers with racemic chalcogran was not significantly different in attractivity compared to (E,Z)-MD with racemic chalcogran, indicating no synergistic or inhibitory effects of the inactive isomers of MD.

Key words

Synergism aggregation pheromone Pityogenes chalcographus Coleoptera Scolytidae chalcogran methyl (2E,4Z)-2,4-decadienoate enantiomers isomers stereoisomers synthesis bioassay structure-activity 

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Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • John A. Byers
    • 1
  • Hans-Erik Högberg
    • 2
  • C. Rikard Unelius
    • 3
  • Göran Birgersson
    • 4
  • Jan Löfqvist
    • 1
  1. 1.Department of EcologyUniversity of LundLundSweden
  2. 2.University College of Sundsvall/HärnösandSundsvallSweden
  3. 3.Department of Organic ChemistryRoyal Institute of TechnologyStockholmSweden
  4. 4.Department of Chemical EcologyGöteborg UniversityGöteborgSweden

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