Nitrofurans

Abstract

Since the first reports of the antibacterial action of nitrofuran derivatives in the 1940s (Dodd and Stillman, 1944; Dann and Möller, 1947) many hundreds of different nitrofuran derivatives have been synthesized and subjected to some degree of biological evalution. Several of these agents, including nitrofurantoin and furazolidone, have been adopted for extensive use in clinical and veterinary medicine. Others have been used as preservatives in human food (AF-2) or added to feed for poultry and swine (e.g., nitrofurazone, furazolidone, furaltadone). With the discovery that certain nitrofuran derivatives are carcinogenic, there has been some curtailment of the use of these agents and further restrictions have recently been proposed (Anon, 1976). Nevertheless, these compounds remain in widespread use and the synthesis of new nitrofuran derivatives continues apace. Indeed, 10% of the 671 references on nitrofurans which were retrieved during a computer search of Chemical Abstracts for the period 1971 to spring 1977 were journal articles dealing with synthesis of new derivatives while an additional 30% referred to patents. Included were items describing antibacterial soaps (Andree and Koppensteiner, 1974), use of nitrofurazone in deodorant (Komura et al., 1974; Kotani and Kageyama, 1976), use of nitrofurylacrylic acid as a stabilizer in wine (Farkas, 1975), nitrofuryl-benzimi-dazole derivatives for use as fungicides (Toth and Toth, 1976), methylthiocyanate derivatives for use in seed treatment (Demecko et al., 1977) and means of incorporating nitrofuryl groups into synthetic fibers to prevent microbial degradation (Gavilova et al., 1974) or to confer antibacterial properties (Siennicki, 1973).