Add time:08/02/2019         Source:sciencedirect.com

Propyl cyclohexaneacetate, a synthetic attractant to the German cockroach, Blattella germanica, appears to consist of a head (cyclohexane ring) and a tail (ester linkage). The tail was modified as regards a number of structural parameters, and the change in activity was interpreted in terms of the corresponding receptor site.Irrespective of the position and direction of the ester linkage, six atoms were optimum for the side chain. The activity increased when the terminal methyl group was replaced with chlorine, and decreased when changed into methylene. The methyl branch in the alcohol unit depressed the activity. The order of attraction among the esters with six atom side chain was as follows: propyl cyclohexaneacetate > cyclohexylmethyl butanoate ≧ ethyl 3-cyclohexylpropanoate ≧ cyclohexyl pentanoate > butyl cyclohexanecarboxylate = 2-cyclohexylethyl propanoate.Ethers, ketones and hydrocarbons which were derived from the esters with six atom side chains by replacing either or both of the carbonyl groups and ether oxygen with methylene(s) were inferior to the parent esters. Their relative activities were in the following order: pentyl cyclohexyl ether > propyl 2-cyclohexylethyl ether > butyl cyclohexyl-methyl ether = pentyl cyclohexyl ketone = butyl cyclohexylmethyl ketone = 6-cyclohexylhexane. The SAR in respect of the ester group resembled that in the muscarinic activity of acetylcholine.

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