Synthesis and Antifungal Activity of Novel Benzimidazol-2- ylcyanoketone Oxime Ethers Containing Morpholine Moiety

A series of benzimidazol-2-ylcyanoketone oxime ethers containing morpholine moiety (4a~4h) were synthesized from 2-benzimidazolyl acetonitrile, sodium nitrite, chloroacetyl morpholine and haloalkane/benzyl chloride via sequential reactions of oximation, substitution and etherification. The structures of the target compounds were elucidated by IR, NMR, MS, and elemental analysis. All the target compounds were tested for in vitro antifungal activities against Botrytis cinerea and Sclerotinia sclerotiorum by the mycelium growth rate test, and the results indicated that some compounds displayed higher antifungal activity as compared to carbendazim, among which the compounds containing 4-fluorobenzyl or 4-chlorobenzyl moiety (4e, 4f) have excellent activity. Keywords oxime ether; benzimidazole; morpholine; antifungal activity