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Comparative molecular field analyses (CoMFA) on the antifungal activity against phytophthora blight fungus of 3-phenylisoxazole and 3-phenyl-2,5-dihydroisoxazol-5-one derivatives  

Sung, Nack-Do (Division of Applied Biology & Chemistry, College of Agriculture & Life Sciences, Chungnam National University)
Lee, Hee-Chul (Dongbu Fine Chemicals Co., Chungchung Province Technology Diffusion Center)
Publication Information
The Korean Journal of Pesticide Science / v.6, no.2, 2002 , pp. 72-79 More about this Journal
Abstract
3D-QSAR between fungicidal activitives ($pI_{50}$) against metalaxyl-sensitive (SPC: 95CC7105) or metalaxyl-resisitant (RPC: 95CC7303) isolate of phytophthora blight fungus (Phytophthora capsici), and a set of 3-phenylisoxazole (A) and 3-phenyl-2,5-dihydroisoxazole (B) derivatives as substrates were conducted using comparative molecular field analyses (CoMFA). The antifungal activities of (A) were generally higher than those of (B). And it is assumed that the most stable conformation of the active substrate was approximately planar from conformational search. The CoMFA models proved a good predictive ability and suggested that the electronic field of substrates were higher than hydropohobic field and steric field requirements for recognition forces of the receptor site. And the factors were strongly correlated (cross-validated $q^2>0.570$ & conventional $r^2>0.968$) with the fungicidal activitives. According to the CoMFA analyses, the selectivity factors for RPC suggested that the sterically bulky groups (C14 & C15) and electron withdrawing groups (C15 & C16) have to be introduced to the ortho, meta and para-position on the benzoyl moiety of substrates.
Keywords
3-phenyl-2,5-dihydroisoxazol-5-ones & 3-phenylisoxazoles; Fungicidal activity; Resistant (RPC) & sensitive (SPC); Phytophthora capsici; Comparative molecular field analysis (CoMFA); Partial least squares regression (PLS);
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