Figure 7
From: Nematicidal and insecticidal activities of halogenated indoles

Proposed chemistry based model for induction of methousis. (A) Iodine-indole complex appears to play a crucial role in inducing methuosis. Iodine in 5-iodoindole and 7-iodoindole appears to induce multiple vacuoles in the body surfaces of M. incognita and B. xylophilus. Subsequent fusion to form giant vacuoles resulted in methuosis (a non-apoptotic type of cell death). (B) The vacuolar phenotypic was not observed in 5F4IPP or 7-fluoro-5-iodoindole treated nematodes, presumably because the fluorine acted as an iodine antagonist. Arrowheads (Red) indicate giant vacuoles, and (C) inductive effect induced by the electronegativity of fluorine in 5F4IPP and its biological effects.