Sex pheromone of the larch caterpillar moth, Dendrolimus superans, from northeastern China

Abstract

The larch caterpillar moth, Dendrolimus superans Butler (Lepidoptera: Lasiocampidae), is a serious pest in the northeastern part of China. In order to develop an effective method for monitoring D . superans , we began a project to identify the sex pheromone of D . superans and preliminary results were published in a note in 2001. Here we report complete laboratory and field results to support the identification. ( Z , E )-5,7-Dodecadienal, ( Z , E )-5,7-dodecadienol, ( Z )-5-dodecenol, and ( Z )-5-dodecenal (100:95:75:71) were identified by gas chromatography (GC) and coupled GC-mass spectrometry in extracts of pheromone glands of female D . superans . However, only ( Z , E )-5,7-dodecadienal elicited strong responses from conspecific male antennae in coupled GC-electroantennography studies. Field tests with synthetic compounds indicated that baits containing ( Z , E )-5,7-dodecadienal as a single component attracted male D . superans moths, whereas addition of one, two, or all three of the possible minor components did not increase the attractiveness of lures. ( Z , E )-5,7-Dodecadienyl acetate, one of the pheromone components in sympatric Dendrolimus species, was antagonistic, but the analog ( Z , E )-5,7-dodecadienyl propionate, another pheromone component in sympatric Dendrolimus species, was not. Since 2005, pheromone traps baited with ( Z , E )-5,7-dodecadienal have been used effectively for monitoring populations of D . superans in various areas of northeastern China.

Identification and Behavioral Evaluation of Sex Pheromone Components of the Chinese Pine Caterpillar Moth, Dendrolimus tabulaeformis

“…In addition, the antennae of male D. tabulaeformis responded to synthetic Z 5, E 7-12:Ald and E 5, Z 7-12:Ald in our GC-EAD analyses, but the two compounds were not detected in pheromone gland extracts. It has been reported that the sex pheromones of D. superans and D. houi consist of Z 5, E 7-12:Ald [7] and E 5, Z 7-12:Ald [9] , respectively. Dendrolimus tabulaeformis is broadly sympatric with D. superans in Inner Mongolia, He'bei, and Liao'ning, and sympatric with D. houi in Shăn'xi and Chongqing.…”

Synthesis and bioactivity of (13Z,15E)‐octadecadienal: A sex pheromone component from Micromelalopha siversi Staudinger (Lepidoptera: Notodontidae)

“…For instance, the derivatives of (5Z,7E)-and (5E,7Z)-dodecadienol are the active sex pheromone components of pine caterpillars. [30][31][32][33] In addition, (11Z,13Z)-hexadecadienal, together with related derivatives, are the critical sex pheromones and attractants in Notodonfidae. 18,34 (8E,10E)dodecadienyl acetate synergizes the codlemone attraction to male Cydia pomonella, and it is also the sex pheromone of Cydia toreuta (Grote) and Melissopus latiferreanus.…”

Identification of Components of the Female Sex Pheromone of the Simao Pine Caterpillar Moth, Dendrolimus kikuchii Matsumura

“…Preparation of Samples Pheromone extracts were prepared as described previously (Kong et al, 2007a, b). Briefly, individual female sex pheromone glands were excised during the peak period of calling (0-2 d-old, 4-7 h into the scotophase) and extracted about 30 min in redistilled hexane (10 μl per gland).…”

“…So far, sex pheromones have been reported for the masson pine caterpillar moth, D. punctatus (Zhao et al, 1993), the pine moth, D. spectabilis (Ando et al, 1982;Kong et al, 2003), the larch caterpillar moth, D. superans (Klun et al, 2000;Kong et al, 2007a), the Yunnan pine caterpillar moth, D. houi (Kong et al, 2007b), and the European pine moth D. pini (Priesner et al, 1984;Kovalev et al, 1993). Sex pheromones components that have been identified from Dendrolimus species are all (5Z,7E)-5,7-dodecadienes with different terminal functional groups (alcohol, acetate, propionate, and aldehyde), except for the sex pheromone of D. houi, which was reported as a mixture of (5E,7Z)-5,7-dodecadien-1-yl acetate (E5,Z7-12:OAc), (5E,7Z)-5,7-dodecadien-1-ol (E5,Z7-12:OH), and (5E,7Z)-5,7-dodecadienal (E5,Z7-12:Ald) (Kong et al, 2007b).…”