Bis(4-fluorophenyl)methyl(1H-1,2,4-triazol-1-yl-methyl)germane, a germanium analogue of the agricultural fungicide flusilazole: synthesis and biological properties

Article abstract of DOI:10.1016/0022-328X(92)88005-4

Bis(4-fluorophenyl)methyl(1H-1,2,4-triazol-1-yl-methyl)germane (2), a germanium analogue of the agricultural fungicide flusilazole (1), has been synthesized from Cl3GeCH2Cl (3) by both a three-step and a four-step synthesis (3 <*> (p-F-C6H4)2Ge(CH2Cl)Br (4) <*>(p-F-C6H4)2Ge(CH2Cl)CH3 (5) <*> 2; 5 <*> (p-F-C6H4)2Ge(CH2I)CH3 (6) <*> 2).The fungicidal properties of 2 have been compared with those of the parent silicon compound 1 (studies on Si/Ge bioisosterism).In various test systems, the Si/Ge analogues 1 and 2 showed comparable fungicidal properties (in activityagainst plant pathogenic fungi; in agar plate diffusion tests and greenhouse evaluations; in activity against human pathogenic fungi; in serial dilution tests).In addition, 1 and 2 displayed comparable potencies in respect of sterol biosynthesis inhibition in Saccharomycopsis lipolytica and Pyricularia oryzae, the mode of action being primarily an inhibition of oxidative C14-demethylation.