Premium
4‐Phenylphenalenones as a template for new photodynamic compounds against Mycosphaerella fijiensis
Author(s) -
Hidalgo William,
Cano Marisol,
Arbelaez Manuela,
Zarrazola Edwin,
Gil Jesús,
Schneider Bernd,
Otálvaro Felipe
Publication year - 2016
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.4055
Subject(s) - mycosphaerella , fungicide , phototoxicity , chemistry , fungal pathogen , stereochemistry , botany , combinatorial chemistry , biology , biochemistry , in vitro , gene
BACKGROUND Evaluation of 4‐phenylphenalenones and structural analogues against the fungal pathogen Mycosphaerella fijiensis (causal agent of black sigatoka disease in bananas) under light‐controlled conditions uncovered some key structural features for the design of photodynamic compounds. RESULTS Structure–activity relationship analysis revealed the importance of a chromophoric aryl‐ketone and a steroidomimetic structural motif in the activity of the assayed compounds. The results pointed to 1,2‐dihydro‐3 H ‐naphtho[2′,1′:3,4]cyclohepta[1,2‐b]furan‐3‐one, which displayed an activity in the range of propiconazole but with photodynamic behaviour. CONCLUSION The present work demonstrates that 1,2‐dihydro‐3 H ‐naphtho[2′,1′:3,4]cyclohepta[1,2‐ b ]heterocyclic‐3‐one derivatives can be used as potential lead compounds for the development of fungicides, relying on a dual mode of action. © 2015 Society of Chemical Industry