Substituted alpha-(phenylhydrazono)phenylacetonitrile derivatives. Part 1: A new class of uncoupler of oxidative phosphorylation.

Substituted alpha-(phenylhydrazono)phenylacetonitrile derivatives have been discovered which constitute a series of potent uncouplers of oxidative phosphorylation. Systematic variation of substituents on both benzene rings has clearly demonstrated the importance of steric congestion around the ionisation site and delocalisation of negative charge in the anionic form. Replacement of the cyano group by other electron-withdrawing groups leads to a dramatic decrease in uncoupling activity.

Substituted alpha-(phenylhydrazono)phenylacetonitrile derivatives. Part 2: Synthesis and biological activity of pro-pesticides.

Pro-pesticides of alpha-(2,6-dichloro-4-trifluoromethylphenylhydrazono)-4-nitrophenylacetonitrile have been prepared and tested against mite and insect pests. Variations in potency and spectrum were observed depending on the choice of cleavable pro-moiety. Cleavage of the pro-moiety was demonstrated in one case by measuring the rate of increase in the uncoupling activity using a mitochondrial preparation.