Sex pheromone produced by the female Japanese beetle: specificity of male response to enantiomers

摘要

(Z)-5-(1-decenyl)dihydro-2(3H)-furanone, isolated from virgin female Japanese beetles, Popilla Japonica, attracted males of the species in field bioassays. However, the synthesized racemic mixture of this compound did not attract male Japanese beetles. The Z- and E-isomers and the saturated analog of both enantiomers of this compound were synthesized stereospecifically. Pure synthetic (R,Z)-5-(1-decenyl)dihydro- 2(3H)-furanone was competitive with live females and with the pheromone isolated from live females in attracting males. Male response was strongly inhibited by small amounts of the (S,Z)-isomer.