Abstract
The biological activity of the Matsucoccus spp. sex pheromones and diene modified analogs has been tested in forests of Israel and Portugal in order to explore the structure-activity relationship of the pine bast scale pheromone/kairomone system. The response of the adult predatory bugs, Elatophilus hebraicus and E. crassicornis and of the brown lacewing, Hemerobius stigma is more selective than that of the conspecific Matsucoccus males. The removal of the terminal methyl group from the diene terminus of both pheromones 1 and 2 eliminates all kairomonal activity but retains moderate pheromonal activity. Addition of a methyl group to the diene terminus of pheromones 1 and 2 sustains full pheromonal and kairomonal activities of the Elatophilus spp. but eliminates entirely the kairomonal activity of H. stigma. Subtle designed alterations in the structure of the diene group, typical of all Matsucoccus pheromones, change the mode of the kairomonal activity markedly.
References
Barrett AGM, Pena M, Willardsen JA (1996) Total synthesis and structural elucidation of the antifungal agent Papulacandin D. J Org Chem 61:1082–1100
Boo KS, Chung IB, Han KS, Pickett JA, Wadhams LJ (1998) Response of the lacewing Chrysopa cognata to pheromones of its aphid prey. J Chem Ecol 24:631–643
Branco M, Franco JC, Carvalho CJ, Mendel Z (2001) Occurrence of Hemerobius stigma Stephens in pine bast scale (Matsucoccus josephi) populations: opportunistic predation or obligatory association. Boll Zool Agric Bachic Ser II 33:397–407
Dunkelblum E (1999) Scale insects. In Hardie J, Minks A (eds) Pheromones of non-lepidopteran insects in agriculture. CABI Publishing, Wallingford, Oxon, pp 251–276
Dunkelblum E, Mendel Z, Gries G, Gries R, Zegelman L, Hassner A, Mori K (1996) Antennal response and field attraction of the predator Elatophilus hebraicus (Hemiptera: Anthocoridae) to sex pheromones and analogues of three Matsucoccus spp. (Homoptera: Matsucoccidae). Bioorg Med Chem 4:489–494
Dunkelblum E, Harel M, Assael F, Mori K, Mendel Z (2000) Specificity of pheromonal and kairomonal response of the Israeli pine bast scale Matsucoccus josephi (Homoptera: Matsucoccidae) and its predator Elatophilus hebraicus (Hemiptera: Anthocoridae). J Chem Ecol 26:1649–1657
Hooper AM, Donato B, Woodcock CM, Park JH, Paul RL, Boo KS, Hardie J, Pickett JA (2002) Characterization of (1R, 4S, 4aR, 7S, 7aR)-dihydronepetalactol as a semiochemical for lacewings, including Chrysopa spp. and Peyerimhoffina gracilis. J Chem Ecol 28:849–864
Kurosawa S, Takenaka M, Dunkelblum E, Mendel Z, Mori K (2000) Pheromonal and kairomonal activities can be separated: synthesis and bioactivity studies of pine bast scale sex pheromones and their analogs. ChemBioChem 1:56–66
Lin GQ, Xu WC (1996) Enzymatic synthesis of (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale. Bioorg Med Chem 4:375–380
Mendel Z, Zegelman L, Hassner A, Assael F, Harel M, Tam S, Dunkelblum E (1995) Outdoor attractancy of males of Matsucoccus josephi (Homoptera: Matsuccocidae) and Elatophilus hebraicus (Hemiptera: Anthocoridae) to synthetic female sex pheromone of Matsucoccus josephi. J Chem Ecol 21:331–341
Mendel Z, Adar K, Nestel D, Dunkelblum E (1997) Sex pheromone traps as a tool for the study of population trends of the predator of a scale insect and for the identification of potential predators for biological control. IOBC/WPRS Bull 20:231–240
Nahm S, Weinreb SM (1981) N-methoxy-N-methylamides as effective acylating agents. Tetrahedron Lett 22:3815–3818
Stowe MK, Turlings TCJ, Loughrin JH, Lewis WJ, Tumlinson JH (1995) The chemistry of eavesdropping, alarm and deceit. Proc Natl Acad Sci USA 92:23–28
Thomas EJ, Whitehead JWF (1989) Cytochalasan synthesis: total synthesis of cytochalasin H. J Chem Soc Perkin Trans 1, 507–518
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This research was supported by the Forest Department of the Jewish National Fund Grant No. 137-0471 and by the EU–FAIR grant no. CT97 3440.
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Mendel, Z., Dunkelblum, E., Branco, M. et al. Synthesis and structure-activity relationship of diene modified analogs of Matsucoccus sex pheromones. Naturwissenschaften 90, 313–317 (2003). https://doi.org/10.1007/s00114-003-0429-0
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DOI: https://doi.org/10.1007/s00114-003-0429-0