Structurally Hybridized Compounds between the Aggregation and Alarm Pheromones of Mite Triggering Conflicted Behavior of <i>Carpoglyphus lactis</i>

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Six structurally hybridized compounds between the mite alarm pheromone neryl formate [(Z)-3,7-dimethyl-2,6-octadienyl formate] and the aggregation pheromone lardolure [1R,3R, 5R,7R-1,3,5,7-tetramethyldecyl formate] were prepared by inserting a methyl residue to 3,7-dimethyloctyl formate skeleton. Compounds possessing allylic Z-double bond in the molecule demonstrated strong repellent activity against the dried fruit mite Carpoglyphus lactis, whereas ones possessing no allylic double bonds behaved as the aggregation kairomone against the same species. Compounds with allylic E-double bond indicated no peculiar activity. As the simplified compound, six 1-methylalkyl formates were prepared. All compounds at 10,000 ppm doses reproduced a state of conflict; motivation for escape at the center and for aggregation at the periphery while the same compounds at 1000, 100 and 10 ppm doses manifested aggregation kairomone activity exclusively.