Synthesis of Farnesyloxy- and Drimanyloxy-Arene Scaffold-Based Hybrid Molecules as Antifungals against Botrytis cinerea

Abstract

There is an increasing interest in the use of biopesticides, which implies the use of living microorganisms, plant and microbial extracts, and natural products isolated from the above-mentioned sources or closely related derivatives. In this regard, 10 farnesyloxy-arenes derivatives (21−25, (±)-26−(±)-30) and 12 drimanyloxyarenes derivatives ((±)-12−(±)-14, (±)-31−(±)-40) were synthesized and tested against the phytopathogenic fungus Botrytis cinerea. In general, the drimanyloxyarenes derivatives were more fungitoxic than their farnesyloxyarene precursors. The most active compounds were (±)-12, (±)-31, and (±)-35, which at a 391 × 10−5 mg/mL dose, were more active than azoxystrobin, while (±)-12 presented an inhibition comparable to that of triclosan. Structure−activity relationships are discussed, as well as the correlation with calculated physicochemical properties such as logP and total polar surface area.