ABSTRACT
This work describes the structural elucidation of the sex pheromone of the soybean stink bug, Pallantia macunaima. The biological activity of the synthetic pheromone was demonstrated by behavioral and EAD experiments. Furthermore, the absolute configuration of the natural pheromone was determined as (6R,10S)-6,10,13-trimethyltetradecan-2-one. This is the first ketone identified as a male-produced sex pheromone in Pentatomidae, and the trivial name, pallantione, was assigned to this novel pheromone molecule.
Subject(s)
Decanoates/isolation & purification , Hemiptera/chemistry , Sex Attractants/isolation & purification , Animals , Decanoates/chemistry , Decanoates/metabolism , Hemiptera/physiology , Male , Molecular Structure , Pheromones/chemistry , Sex Attractants/chemistry , Sex Attractants/metabolism , StereoisomerismABSTRACT
Olfactometer bioassays showed that odors from mature Thyanta perditor males attracted females but not males. Furthermore, odors from females did not attract either sex, indicating that like other phytophagous pentatomid bugs, the males produce a sex pheromone. Attraction appeared to peak in late afternoon to evening. The headspace volatiles collected from male and female T. perditor were analyzed by GC-MS and HPLC. A male-specific compound, methyl (2E,4Z,6Z)-decatrienoate (2E,4Z,6Z-10:COOMe), was identified along with a number of other compounds found in extracts from both sexes. Bioassays carried out with 2E,4Z,6Z-10:COOMe showed it was as attractive to females as the crude extract of male volatiles, suggesting that the male-produced sex pheromone consists of 2E,4Z,6Z-10:COOMe as a single component. Consecutive volatiles collections from males showed that 2E,4Z,6Z-10:COOMe began appearing in extracts from males about 9 d after the final molt, as the males became sexually mature.