Phytotoxic Activity and Metabolism of Botrytis cinerea and Structure−Activity Relationships of Isocaryolane Derivatives

Abstract

Research has been conducted on the biotransformation of (8S,9R)-isocaryolan- 9-ol (4a) and (1S,2S,5R,8S)-8 methylene-1,4,4-trimethyltricyclo[6.2.1.02,5]undecan-12-ol (5a) by the fungal phytopathogen Botrytis cinerea. The biotransformation of compound 4a yielded compounds 6−9, while the biotransformation of compound 5a yielded compounds 10−13. The activity of compounds 4a and 5a against B. cinerea has been evaluated. (8R,9R)- Isocaryolane-8,9-diol (6), a major metabolite of compound 4a, shows activity compared to its parent compound 4a, which is inactive. The effect of isocaryolanes 3, 4a, and 5a, together with their biotransformation products 6−8, 10, and 14−17, on the germination and radicle and shoot growth of Lactuca sativa (lettuce) has also been determined. Compounds 7−13 are described for the first time.