Insecticidal 1-(alkynylalkyl)-3-cyano-2,6,7-trioxabicyclo [2.2.2.]octanes
1993
Smith, I.H. | Budd, T.C. | Sills, J. | Cassida, J.E.
The high insecticidal activity and potency at the insect GABA-gated chloride channel of 4-alkyl-3-cyano-2,6,7-trioxabicyclo[2.2.2]octanes with the 1-(4-ethynylphenyl) substituent is also achieved with the corresponding 1-(hex-5-ynyl) analogs. Conceptually the four-methylene linkage resembles the spatial characteristics of a phenyl ring and shows the ethynyl group to occupy the same area of receptor space as when attached at the 4-position of an aryl moiety. This is the finest example of chloride channel blockers with the ability to replace a phenyl group by a conformationally flexible alkyl linkage and retain a significant portion of the activity.
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