AbstractA series of pyridylcarbamates showed high potency against cucumber gray mould (Botrytis cinereaPers.). The most potent compound, propargyl‐N‐(6‐ethyl‐5‐iodo‐2‐pyridyl)carbamate was effective against an isolate sensitive to benzimidazole and dicarboximide fungicides as well as against an isolate resistant to both types of compound. QSAR analyses and molecular modelling studies were carried out to investigate the structural requirements for highly active compounds and the structural feature of the binding site of each strain. Significantly different QSAR equations were obtained only for substituents at the 6‐position of the pyridine ring. An ethyl‐sized pocket or an ethyl terminal recognition was suggested in the case of the sensitive or resistant isolate respectively. These results could explain the phenomenon of negatively correlated cross‐resistance between benzimidazoles andN‐phenylcarbamate fungicides. Substituent effects at the 5‐ or 2‐position were governed by steric factors. Substituent effects at the 3‐position were explained by steric hindrance or by conformational effects. The propargyl‐substituted compound above was the most desirable o