Sex pheromone of the persimmon fruit moth, Stathmopoda masinissa: identification and laboratory bioassay of (4E, 6Z)-4,6-hexadecadien-1-ol derivatives.
Three electroantennogram (EAG)-active components were detected by gas chromatography coupled to an electroantennographic detector (GC-EAD) analysis of a hexane extract of the pheromone glands of the persimmon fruit moth, Stathmopoda masinissa. These compounds were identified as (4E,6Z)-4,6-hexadecadienal (E4,Z6-16:Ald) and the corresponding acetate (E4,Z6-16:OAc) and alcohol (E4,Z6-16:OH) by mass spectral, GC retention time (RT), and microchemical test data. The characteristic base peak of the aldehyde at m/z 84 provided a crucial piece of information suggesting the possibility of a 4,6-diene structure. The (4E,6Z)-isomer elicited the strongest EAG responses among the four geometrical isomers of each synthetic 4,6-hexadecadienyl compound. In a laboratory bioassay, only E4,Z6-16:OAc elicited male moth behavioral activity significantly different from the control; the activity of the acetate was not affected by addition of the aldehyde and alcohol. A preliminary field trial confirmed that E4,Z6-16:OAc as a single component attracted male moths. The possible roles of E4,Z6-16:Ald and E4,Z6-16:OH as components of lures for field use remain to be determined.
Naka
Hideshi
H
Laboratory of Applied Entomology, Faculty of Agriculture, Gifu University, Gifu 501-1193, Japan. chun@wakaba.com
Vang
Le Van
le V
Inomata
Shin-Ichi
S
Ando
Tetsu
T
Kimura
Takayoshi
T
Honda
Hiroshi
H
Tsuchida
Koji
K
Sakurai
Hironori
H
D000466:Alkadienes / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D004594:Electrophysiology; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D007536:Isomerism; D008297:Male; D009036:Moths / Q000502:physiology*; D009068:Movement; D012724:Sex Attractants / Q000302:isolation & purification* / Q000494:pharmacology*
C482757:(4E,6Z)-4,6-hexadecadien-1-ol; D000466:Alkadienes; D012724:Sex Attractants