1(R)-(2,6-CIS-DIMETHYLMORPHOLINO)-3(S)-(PARA-TERT-BUTYLPHENYL)CYCLOPENTANE - A REPRESENTATIVE OF A NOVEL, POTENT CLASS OF BIO-RATIONALLY DESIGNED FUNGICIDES

Inhibition of the DELTA(8)-DELTA(7) sterol isomerase in the ergosterol biosynthesis pathway is known to lead to fungistatic or even fungicidal effects. Our approach to the rational design of new putative inhibitors of the enzyme was based on the assumed mechanism of the enzymic transformation and in particular on the structure of the unstable carbocationic intermediate, i.e. the 'transition-state-analogue' principle. The synthesis and the biological properties of 1(R)-(2,6-cis-dimethylmorpholino)-3(S)-(p-tert-butylphenyl)cyclopentane, a representative of a novel, potent class of rationally designed fungicides, as well as the synthesis and biological activities of several other related compounds are described and discussed.