Pheromone of female Japanese beetle

Z) 5 Tetradecen 4 olide (sex pheromone of female Japanese beetle)... 

Females of several species use (R)-5-[(lZ)-l-octenyl]oxacyclopentan-2-one, buibuilactone 69 [ 140-144]. The first y-lactone identified from a scarab beetle was (R)-5-[(Z)-l-decenyl]oxacyclopentan-2-one, japonilure 70, the female produced sex pheromone of the Japanese beetle Popillia japonica [145]. Both 69 and 70 are components of specific blends of several species [140-143]. The Japanese beetle is extremely sensitive to the non-natural enantiomer of his pheromone as little as 1% of the (S)-enantiomer inhibits the attractiveness of the pheromone [ 145]. With respect to species discrimination, this is particularly... 

The sex pheromone of the Japanese beetle, also given off by the females, has been made by chemists. As little as 5 pg (micrograms, note ) was more effective than four virgin females in attracting the males. 

Japonilure R), the sex pheromone of the female Japanese beetle. Papilla japonica and its enantiomer, (5)-(+)-(5Z )-tetradecen-4-olide, which is the pheromone of the Osaka beetle, Anomala osakana have been synthesized using a highly convergent procedure and in satisfactory overall yields. 

Tumlinson J. H., Klein M. G., Doolittle R. E., Ladd T. L. and Proveaux A. T. (1977) Identification of the female Japanese beetle sex pheromone inhibition of male response by an enantiomer. Science 197, 789-792. 

In particular, the importance of chirality in diverse pheromone systems has been reviewed recently (Mori, 1998). For example, olive fruit flies (Bactrocera oleae) emit racemic 2 the males detect the R enantiomer, while females detect the S (Haniotakis et al., 1986). The sex pheromone of the Osaka beetle (Anomala osakana) is 4a, while the closely related Japanese beetle (Popilia japonica) uses 4b (Table 16.1). Interestingly, 4a is a powerful behavioral antagonist in P. japonica (Tumlinson et al., 1977). The hemlock looper, Lambdina fiscellaria, responds only to (5R, 1 S)-5,I I -dimethylheptadecane. The enantiomer or the R/R or S/S diastereomers do not elicit electrophysiological or behavioral responses (Li et al., 1993). Table 16.1 gives an overview of those species where proteins from the pheromone olfactory system have been identified. 

Females of the Japanese beetle, Popilla japonica, synthesize one of the few lactonic sex pheromones that have been identified in insects (52). Tumlinson et aK (52) have recently identified the powerful sex pheromone of this insect as (R.ZJ-5-(1-decenyl)dihydro-2(3H)-furanone (X). In addition to the Z-isomer, the -isomer is also present as well as the saturated... 

The sex attractant of the female Japanese beetle, Popillia japonica, which attracts males, is (Z)-5-(l-decenyl)dihydro-2(3//)-furanone (73). The pure synthetic R,Z-isomer (144, Scheme 27) was competitive with females, and male response was strongly inhibited by small amounts of the 5,Z-isomer. The enantiomeric composition of the natural product has not been determined. The female also produces minor amounts of both the -isomer and the saturated analog but the roles of these compounds has not been established. Females of the California red scale, Aonidiella aurantii, emit a pheromone that attracts males (331). Two compounds have recently been identified and synthesized 3-methyl-6-isopropenyl-9-decen-l-yl acetate (332 a) and (Z)-3-methyl-6-isopropenyl-3,9-decadien-1-yl acetate (333, Scheme 50) (75). The four enantiomers of the latter compound were synthesized and only the R,Z-isomer proved to be attractive to male red scale. 

There are two other factors worth noting in regard to the Japanese beetle pheromone. A single compound apparently possesses all the activity of the pheromone. This is even more surprising when we note that the material obtained from females contained about 15% of the (E) Isomer and 3% of the analog with a saturated side chain. However, these other two compounds had no effect on the activity of the (R)(Z)-isomer when added in the appropriate ratios whether the racemic or the pure enantiomeric forms were used. 

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