SYNTHESIS AND FUNGICIDAL ACTIVITY OF ALICYCLIC DIAMINES

摘要

As part of an ongoing program of work on polyamine analogues, a number of alicyclic diamines were synthesized and examined for fungicidal activity. The alicyclic diamine 1,2-bis(aminomethyl)4,5-dimethylcyclohexa-1,4-diene (BAD), synthesized as the dihydrochloride salt, controlled the important crop pathogen Erysiphe graminis f.sp hordei. Greatest control off, graminis was achieved when BAD was applied 2 days postinoculation. The alicyclic diamines trans-4,5-bis(aminomethyl)1,2-dimethylcyclohex-1-ene (trans-BAD) and the cis-isomer (cis-BAD), as well as 1,2-bis(aminomethyl)cyclopentene (BACP) and trans-1,2-bis(dimethylaminomethyl)cyclo (TCCBM), were also synthesized as their dihydrochloride salts. trans-BAD was found to possess greater fungicidal activity than the cis-isomer against E. graminis, while BACP and TCCBM both gave >80% control of powdery mildew infection. Since the powdery mildew fungus cannot be grown axenically, the effects of the alicyclic diamines on polyamine metabolism were examined using the oat leaf stripe pathogen, Pyrenophora avenae. BAD and derivatives had little effect on polyamine metabolism in the fungal pathogen P. avenae. It seems clear, therefore, that the antifungal activity of these derivatives may not be associated with altered polyamine metabolism.