Japanese beetle

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

Bacillus popilliae Bacteria Japanese beetle larvae in soil... 

In insect control, PEA has been considered as a mosquito repeUant (68), and its acetate has been used as an ingredient in Japanese beetle bait (69). The alcohol also has bacteriostatic action and antiflmgicidal properties (70—73), and it has been claimed as a surface-active agent (74). 

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. 

Japanese beetle, Popillla japonica from chlordane-treated lawn total chlordane-related compounds Up to 15,600 FW (may be a chlordane-resistant strain) 106... 

Sometimes the inactive isomer may interfere with the active isomer and significantly lower its activity. For example, when the ( /-derivative of the sex pheromone of a Japanese beetle is contaminated with only 2% of its enantiomer, the mixture is three times less active than the optically pure pheromone. The pheromone with as little as 0.5% of the (.S )-enantiomer already shows a significant decrease of activity.3... 

Glaser RW, Farrell CC. (1935) Field experiments with the Japanese beetle and its nematode parasite. J NY Entom Soc 43 345. 

Glaser RW. A pathogenic nematode of the Japanese beetle. J Parasitol. 1932 18 199. 

Fig. 10 TLC plate showing degradation of (R)- and (S)-japonilure (upper spots) by esterases from the legs (Leg) and antennae (Ant) of the Japanese beetle. The corresponding hydroxy-acids appear as lower bands. Note the slower degradation of the behavioral antagonist, (S)-japonilure, by sensillar esterase(s) from the antennae. Neither (R)- nor (S)-japonilure is degraded in control experiments (data not shown) under the same conditions, i.e., with the compounds incubated in buffer without Japanese beetle tissue extracts...

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... 

Currently, other minor applications include treatment of felled logs for bark beetles, termite control, control of wax moths in beehives, spot treatment of milling machinery, Japanese beetle control in ornamental plants, and as a chemical intermediate for dyes, resins, waxes, and gums (HSDB 1989). 

All creatures, whatever their size, risk attack by pests and diseases. They are part of a great food chain. Ladybugs prey on aphids, robins eat Japanese beetles, and toads devour slugs. 

Adult Japanese beetles are chunky, metallic blue-green, l -in (1-cm) beetles with bronze wing covers, long legs, and fine hairs covering their bodies. They emerge in midsummer and lay eggs in... 

Pheromone traps are mechanical devices containing scents that attract a specific insect species. Pheromone traps are available for Japanese beetles and a wide range of other insects. The insects are enticed into the trap by the scent and are unable to get out. These traps attract pests from a considerable distance, but do not immediately catch all the insects they attract. They are best used some distance from the garden to attract the insects away from, not into. 

Another bacterium, ""Bacillus papillae", causes milky spore disease in grubs of Japanese beetles. This product is commercially available as Doom or Japademic but may be very hard to locate. The powder is applied to the grotttrd and, in time, infects the grabs over large areas. Once established, the bacteria may sttrvive in the soil for several years. 

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. 

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. 

Asymmetric reduction of Myny ketones. The (Reform of the complex (1) reduces alkynyl ketones to optically active propargylic alcohols (usually R) in 65-85% chemical yield and in 85-95% optical yield use of the (S)-form of 1, as expected, results in the epimeric alcohol. This reduction was used in a synthesis of the natural Japanese beetle pheromone (2, equation I).1... 

Chiral y-iactones (10, 321). Midland3 has extended his synthesis of chiral y-lactones to an efficient synthesis of the sex pheromone (2) of the Japanese beetle. The overall optical yield of (2) from optically pure a-pinene is 97%. 

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. 

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. 

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