Mandibular gland secretions of the male beewolvesPhilanthus crabroniformis, P. barbatus, andP. pulcher (Hymenoptera: Sphecidae)

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Abstract
The composition of the territorial marking pheromones from mandibular glands of males of the beewolvesPhilanthus crabroniformis, P. barbatus, andP. pulcher have been determined. The structures of the components were elucidated by gas chromatography-mass spectrometry and gas chromatography-Fourier transform infrared spectroscopy. The major compound ofP. crabroniformis is isopropyl tetradecanoate, with somewhat lesser amounts of 2-tridecanone, 3-methyl-3-butenyl tetradecanoate, and 92∶8 (Z)∶(E)-11-eicosen-1-ol. The major compounds ofP. barbatus are ethyl tetradecanoate and hexadecanal, which are present in approximately a 60∶40 ratio. These two compounds comprise over 95% of the neutral lipids. Also present in lesser amounts are ethyl dodecanoate, tetradecanal, hexadecan-1-ol, a Δ x -octadecen-1-ol, and octadecan-1-ol. The major compounds ofP. pulcher are ethyl (Z)-7-hexadecenoate and geranylgeraniol acetate, which comprise nearly 90% of the neutral lipid fraction, with smaller amounts of tetradecanal, pentadecanal, and ethyl hexadecanoate; trace amounts of Δ x hexadecenal, hexadecanal, and octadecanal are also present.