(1) is shown by its synthesis to be the major component of the maleproduced aggregation pheromone of the broad-horned flour beetle (Gnatocerus cornutus).
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.
New syntheses were achieved to secure matsuone (1), the pheromone of the pine scale Matsucoccus matsumurae, that of M. feytaudi (2), and that of M. josephi (3). Five analogues (4-8) of 1, 2, and 3 were synthesized and their bioactivities studied. The pheromone analogue 7 showed relatively strong pheromonal activity toward M. josephi, while it was inactive as a kairomone toward the predator Elatophilus hebraicus. Similarly, analogue 8 acted as a pheromone for M. feytaudi, but it did not attract any of its local predators. The M. feytaudi pheromone 2 exhibited strong kairomonal activity toward E. hebraicus, but was not active as a pheromone mimic to attract M. josephi.
Both the enantiomers of 9‐methylgermacrene‐B (1) were synthesized from the enantiomers of methyl 3‐hydroxy‐2‐methylpropanoate (2). The male‐produced sex pheromone of the sandfly Lutzomyia longipalpis (the vector of the protozoan parasite Leishmania chagasi) from Lapinha, Brazil, was identified as (S)‐1 by GC comparison.
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