The culture medium of the mould Caldariomyces fumagowas extracted with three organic solvents and the extracts were analysed by GC-MS. Twelve halogen-containing metabolites were found in the dichloromethane extract. Seven of these compounds were sufficiently abundant to allow the identification of the new halometabolites, 2,2-dichloroethanol, 1,3-dichloropropanol-2, 1,1,3-trichloropropanol-2, 1,1,3,3-tetrachloropropanol-2, 2-(3-chloro-4-hydroxyphenyl)ethanol and 2-(3,5-dichloro-4-hydroxyphenyl)ethanol in addition to the well-known caldariomycin (2,2-dichloro-1S,3S-dihydroxycyclopentane). Their possible biosynthetic routes and the implications for the reaction mechanism of the Caldariomyceshalogenating enzyme chloroperoxidase are discussed.