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Female Sex Pheromone of the Yunnan Pine Caterpillar Moth Dendrolimus Houi: First (E,Z)-Isomers in Pheromone Components of Dendrolimus spp

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Abstract

The Yunnan pine caterpillar Dendrolimus houi Lajonquière is a serious defoliator of coniferous forests in southwestern China. Gas chromatography–electroantennography (GC–EAG) analyses of extracts of female sex pheromone glands of D. houi moths revealed the presence of three compounds eliciting antennal responses. These were identified as (5E,7Z)-5,7-dodecadien-1-ol (E5,Z7-12:OH), (5E,7Z)-5,7-dodecadien-1-yl acetate (E5,Z7-12:OAc), and (5E,7Z)-5,7-dodecadienal (E5,Z7-12:Ald) by comparison of their GC retention indices, mass spectra, and EAG activities with those of synthetic standards. Average amounts of E5,Z7-12:OH, E5,Z7-12:OAc, and E5,Z7-12:Ald per calling virgin D. houi female were 14.7 ± 12.9 ng (± SD), 5.8 ± 5.4 ng, and 0.8 ± 1.4 ng, respectively, in a ratio of 100:39.7:5.6. These three components were also collected from the headspace of calling virgin female moths by solid-phase microextraction (SPME). In addition, trace quantities of (Z)-5-dodecen-1-ol (Z5-12:OH), (5Z,7E)-5,7-dodecadien-1-ol (Z5,E7-12:OH), (5E,7E)-5,7-dodecadien-1-ol (E5,E7-12:OH), (5Z,7E)-5,7-dodecadien-1-yl acetate (Z5,E7-12:OAc), (5Z,7Z)-5,7-dodecadien-1-yl acetate (Z5,Z7-12:OAc), and (5E,7E)-5,7-dodecadien-1-yl acetate (E5,E7-12:OAc) were tentatively identified in female pheromone gland extracts by selected ion monitoring GC-MS. Field trapping experiments showed that E5,Z7-12:OH, E5,Z7-12:OAc, and E5,Z7-12:Ald were essential for attraction of male D. houi moths. Traps baited with a 20:1:1 blend (alcohol/acetate/aldehyde) loaded on gray rubber septa were as effective as traps baited with virgin female moths. The optimum ratio of acetate to aldehyde was 1:1, and this ratio was more critical than the ratio of either compound to the alcohol. This represents the first example of (E,Z)-isomers in pheromone blends of Dendrolimus species.

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Acknowledgments

The authors thank Lou Yong-gen for his critical review of the manuscript. We are also grateful to John A. Byers and Blanka Kalinová for their constructive comments and revision of the manuscript. Thanks are also due to Jocelyn G. Millar for technical assistance and advice. We are indebted to Liu Hong-ping, Tong Qing, and Mao Jia-ying and their staffs for assistance with field experiments. This work was supported by the National Natural Science Foundation of China (Grant No. 30300275).

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Authors and Affiliations

  1. Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Beijing, 100091, China

    Xiang Bo Kong, Zhen Zhang & Hong Bin Wang

  2. The Key Laboratory of Forest Ecology and Environment, State Forestry Administration, Beijing, 100091, China

    Xiang Bo Kong, Zhen Zhang & Hong Bin Wang

  3. Institute of Zoology, Chinese Academy of Sciences, Beijing, 100080, China

    Cheng Hua Zhao

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  1. Xiang Bo Kong
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Correspondence to Xiang Bo Kong.

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Kong, X.B., Zhang, Z., Zhao, C.H. et al. Female Sex Pheromone of the Yunnan Pine Caterpillar Moth Dendrolimus Houi: First (E,Z)-Isomers in Pheromone Components of Dendrolimus spp. J Chem Ecol 33, 1316–1327 (2007). https://doi.org/10.1007/s10886-007-9313-2

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  • DOI: https://doi.org/10.1007/s10886-007-9313-2

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