Houseflies reduction

Tillman-Wall J. A., Vanderwel D., Kuenzli M. E., Reitz R. C. and Blomquist G. J. (1992) Regulation of sex pheromone biosynthesis in the housefly, Musca domestica relative contribution of the elongation and reductive step. Arch. Biochem. Biophys. 299, 92-... 

Examination of the data shows that the first entry in the Table 1 had exceptionally high activity on aphids and mites with TI values of 1750 and 3192, respectively. For houseflies and corn earworms this compound was less active than the standard parathion. Increases in size of the substituent R significantly reduced the activity against all insects except the corn earworm where a major reduction only occurred when the hydrogen was replaced by ethyl and larger groups. 

The housefly (Musca domestica) uses the hydrocarbon (Z)-9-tricosene (318 in Scheme 58) as the major component of its sex pheromone. Simple syntheses involve Wittig coupling 153, 154) or alkylation of a terminal alkyne and subsequent reduction 155, 156) to afford the desired Z-isomer in ca. 95% purity. Erucic acid 157, 158) or oleic acid 159, 160) have served as starting material of known Z stereochemistry. The transition metal-catalyzed olefin cross-metathesis reaction has been applied by Rossi 161) to synthesize (318) as a mixture of /Z-isomers together with the other possible Cis and C28 olefins (Scheme 58). 

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