A new pheromone of the silkworm moth Bombyx mori

The female silkmoth Bombyx mori L. emits a second pheromone component bombykal (E-10, Z-12-hexade-cadien-1-al) in addition to the well-known sexual attractant bombykol (E-10, Z-12-hexadecadien-1-ol). Bombykal stimulates its own specialized and highly sensitive olfactory cells of the male moth. Surprisingly, the aldehyde inhibits the release of the male's wing-fluttering response to bombykol.     

Benzoic acid, a stimulant of odorant receptors of Bombyx mori, is rapidly metabolized to N-benzoylserine on the antennae

Summary. Benzoic acid is a known stimulant of olfactory receptor cells in trichoid sensilla on the antennae of adult females of Bombyx mori. Exposure of freshly excised antennae, from B. mori females and males, to vapours of [¹⁴C]-benzoic acid revealed that the adsorbed acid is rapidly metabolized (15% conversion in 10 s), suggesting the presence of a highly active enzymatic system. The major product could be identified as N-benzoylserine by use of [²H₅]-benzoic acid, and mass spectrometry linked to a gas chromatograph (GC-MS) or a liquid chromatograph (LC-MS), for analysis of the metabolites. The conjugation of benzoic acid with an amino acid apparently represents a novel mode for the rapid deactivation of odorant molecules. Received 26 March 2001.     

Unusual pheromone chemistry in the navel orangeworm: novel sex attractants and a behavioral antagonist

Using molecular- and sensory physiology-based approaches, three novel natural products, a simple ester, and a behavioral antagonist have been identified from the pheromone gland of the navel orangeworm, Amyelois transitella Walker (Lepidoptera: Pyralidae). In addition to the previously identified (Z,Z)-11,13-hexadecadienal, the pheromone blend is composed of (Z,Z,Z,Z,Z)-3,6,9,12,15-tricosapentaene, (Z,Z,Z,Z,Z)-3,6,9,12,15-pentacosapentaene, ethyl palmitate, ethyl-(Z,Z)-11,13-hexadecadienoate, and (Z,Z)-11,13-hexadecadien-1-yl acetate. The C₂₃ and C₂₅ pentaenes are not only novel sex pheromones, but also new natural products. In field tests, catches of A. transitella males in traps baited with the full mixture of pheromones were as high as those in traps with virgin females, whereas control and traps baited only with the previously known constituent did not capture any moths at all. The navel orangeworm sex pheromone is also an attractant for the meal moth, Pyralis farinalis L. (Pyralidae), but (Z,Z)-11,13-hexadecadien-1-yl acetate is a behavioral antagonist. The new pheromone blend may be highly effective in mating disruption and monitoring programs.