Fungicidal sesquiterpene dialdehyde cinnamates from Pseudowintera axillaris

Bioactivity-directed separation of a foliage extract from the New Zealand shrub Pseudowintera axillaris led to a compound with fungicidal activity against the plant pathogen Phytophthora infestans. This was identified as a new sesquiterpene dialdehyde cinnamate named paxidal. Two 6-hydroxy derivatives were present at lower levels in the extract. A further nine derivatives were synthesized from these natural products for a structure-activity study against a range of important food crop pathogens. The cinnamate group was important for fungicidal effects, and protection of the dialdehyde as a dimethyl acetal gave more potent, broader spectrum activity.