Popillia japonica, Japanese beetle

Beetle, Japanese Popillia japonica) Beetle, lady Ceratomegilla fuscilabrus) Mealworm, yellow (Tenebrio nwlitor) Weevil, bean (Acanthoscelides obtectus) (196-276) (83-180) (176-222) m 114 f 146 13.1 m(2.9-6.8) f(2.8-8.3)... 

Enantiomerically pure japonilure [(4JR,5Z)-5-tetradecen-4-olide, 26] is commercially important to attract the Japanese beetle (Popillia japonica), because only pure (4.R,5Z)-26 is bioactive, while ( )-26 is totally inactive. Synthesis of (4 ,5Z)-26 via enzymatic resolution of racemic intermediates was first reported by Sugai [63], and then further studied by Fukusaki [64] to establish the process as summarized in Scheme 39. Lipase PS (Amano) from Pseudomonas sp. and lipase OF (Meito) from Candida cylindracea were shown to be the enzymes of choice. 

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... 

Japanese beetle, Popillia japonica from chlordane-treated lawn total chlordane-related compounds June beetle, Phyllophaga sp. found in stomach of chlordane-polsoned screech owl (Otus asio)... 

Loughrin, J. H., Potter, D. A. and Hamiltonkemp, T. R. (1995b). Volative compounds induced by herbivory act as aggregation kairomones for the japanese-beetle (Popillia japonica Newman). Journal of Chemical Ecology 21 1457-1467. 

Nikonov A. A. and Leal W. S. (2002) Peripheral coding of sex pheromone and a behavioral antagonist in the Japanese beetle, Popillia japonica. J. Chem. Ecol. 28, 1075-1089. 

Japanese beetle (Popillia japonica) Bacillus popilliae... 

A mixture of geraniol and eugenol is more attractive to the Japanese beetle Popillia japonica Newman) than either chemical alone 42y 13). This might be called odor synergism. Very little work has been done along this line. 

Popillia japonica. See Japanese beetles Poplar. See Populus... 

Tumlinson et al. (1977) were the first to demonstrate inhibition of response to a pheromone by its enantiomer. They synthesised stereospecifically the Z- and f-isomers of both enantiomers of (Z)-5-(l-decenyl)dihydro-2(3H)-furanone, the sex pheromone of the Japanese beetle, Popillia japonica. The purely synthetic (R, Z)-5-(l-decenyl)dihydro-2(3H)-furanone (18) was as effective as the natural isolated pheromone, but male response was strongly inhibited by small amounts of the S- and Z-isomer. 

Treatment of the 1,5-diene (Z,Z)-CHD=CHCH2CH2CH=CHD with potassium permanganate results in stereospecific oxidative cycloaddition to give 40% of the tetrahydrofuran (25), which possesses four chiral centres the (E,E)-isomer behaves in an analogous fashion. " 2,2-Dialkoxytetrahydrofurans are formed from epoxides and keten acetals thus epichlorhydrin reacts with MeCH=C(OMe)2 in the presence of zinc chloride to afford compound (26). The chloro-furanone (27) is obtained as a mixture of cis- and trans-isomers from styrene and trimethylsilyl dichloroacetate in the presence of bis(triphenylphos-phine)ruthenium(ii) chloride. Total syntheses of both enantiomers of the pheromone (28) of the Japanese beetle [Popillia japonica) and of chalcogran (29), the principal pheromone of Pityogenes chalcographus (L.), have been described. 

The Japanese beetle (Popillia japonica) sex pheromone (144) is a lactone with an unsaturated side chain (Scheme 27). Optically active (7 )-(-)-glutamic acid (140 a) served as the starting material in the synthesis by Tumlinson et al 73) shown in Scheme 27. After ring closure with retention of configuration and formation of the aldehyde, inverse addition of the Wittig reagent afforded the desired R,Z configuration. 

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. 

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