Grain beetles

Lipases also catalyze the intramolecular transesterification (lactonization) of hydroxy esters. Macrolactonization of a racemic hydroxy ester in the presence of PSL provided the corresponding (R)-lactone (Figure 6.22). This compound is the naturally occurring enantiomer of the pheromone produced by the merchant grain beetle [70]. Chemical macrolactonizations require high dilution to minimize... 

Collins, PJ. 1985. Resistance to grain protectants in field populations of the sawtoothed grain beetle in southern Queensland. Austral. Jour. Exp. Agric. 25 683-686. 

Lord, J.C. 2001. Desiccant dusts synergize the effect of Beauveria bassiana (Hyphomycetes Moniliales) on stored-grain beetles. J. Econ. Entomol. 94, 367-372. 

Loschiavo, S.R. and Smith, L.B. 1970. Distribution of the merchant grain beetle, Oryzaephilus mercator (Silvanidae Coloeptera) in Canada. Can. Entomol. 102, 1041-1047. 

Mowery, S.V., Mullen, M.A., Campbell, J.F., and Broce, A.B. 2002. Mechanisms underlying sawtoothed grain beetle (Oryzaephilus surinamensis [L.]) (Coleoptera Silvanidae) infestation of consumer food packaging materials. J. Econ. Entomol. 95, 1333-1336. 

Cucujidae.Silvanidae/Laemophloeidae (Flat Bark Beetles, Grain Beetles). 125... 

The male-produced aggregation pheromone of the square-necked grain beetle, Cathartus quadricollis has been identified to be (3R,6 )-3-acetoxy-7-methylnon-6-ene 157 [297]. The compound, termed quadrilure, is attractive to both sexes, however, females are more sensitive at low concentrations. The (S)-enantiomer is biologically inactive. 

Advent of ring-closing olefin metathesis reaction has influenced the synthetic strategy of pheromones very much. For example, the racemate of a macrolide pheromone such as (5Z,13S)-5-tetradecen-13-olide (29) (aggregation pheromone of the flat grain beetle, Cryptolestes pusillus) could readily be synthesized as shown in Scheme 42 [67]. Unfortunately, ( )-29 prepared by this method was a mixture of c/s, trans-isomers (Z/E=69 31). (S)-5-Hexadecanolide (27) was also synthesized by means of ring-closing olefin metathesis as shown in Scheme 43 [68]. 

One of the most efficient methods to fight lice and thereby to contain and eliminate typhus—but also to kill other vermin like grain beetles, bugs, cockroaches, termites, mice, rats and many more—is their poisoning with highly volatile hydrogen cyanide. 

The biosynthesis of the cucujolides was examined in the merchant grain beetle, O. mercator Fauvel, and the rusty grain beetle, C. ferrugineus (Stephens), using radio- and stable isotope-labeled precursors (Vanderwel et al., 1990,1992b). 

Pierce A. M., Pierce H. D., Jr, Johnston B. D., Oehlschlager A. C. and Borden J. H. (1988) Aggregation pheromone of square necked grain beetle, Cathartus quadricollis (GUER). J. Chem. Ecol. 14, 2169-2184. 

Vanderwel D., Johnston B. and Oehlschlager A. C. (1992b) Cucujolide biosynthesis in the merchant and rusty grain beetles. Insect Biochem. Molec. Biol. 22, 875-883. 

White P. R., Chambers J., Walter C. M., Wilkins J. P. G. and Millar J. G. (1989) Sawtoothed grain beetle Oryzaephilus surinamensis (L.) (Coleoptera, Silvanidae) collection, identification, and bioassay of attractive volatiles from beetles and oats. J. Chem. Ecol. 15, 999-1013. 

Z.13S)-5- Tetradecen-13- olide S Flat grain beetle Cryptnlestes pusiUus) A Grubbs Olefin methatesis [155]... 

Conyers, S.T. and Bell, C.H. (1997) The effect of modified atmospheres on the juvenile stages of six grain beetles. Proceedings of the International Conference on Controlled Atmosphere and Fumigation in Stored Products, Nicosia, Cyprus, April 1996, Dona-haye, E.J., Navarro, S. and Vamava, A., pp. 73-81. 

Evans, D.E. (1983) The influence of relative humidity and thermal acclimation on the survival of adult grain beetles in cooled grain. Journal of Stored Products Research 19, 173-180. 

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