Influence of substituted phenyl backbone on the fungicidal activity of phenyl or 2-pyridyl substituents in bis-aromatic ${\alpha},{\beta}$-unsaturated ketone derivatives

비스 방향족 $\alpha, \beta$ -불포화 케톤 유도체중 2-pyridyl 및 phenyl 치환체의 항균성에 관한 치환 phenyl backbone의 영향

  • Sung, Nack-Do (Division of Applied Biology & Chemistry, Chung-nam National University) ;
  • Yu, Seong-Jae (Division of Applied Biology & Chemistry, Chung-nam National University) ;
  • Choi, Kyoung-Seob (Division of Applied Biology & Chemistry, Chung-nam National University) ;
  • Kim, Hyun-Jae (Kyung Ju Research institute, Kyung Nong Corporation)
  • 성낙도 (충남대학교 농과대학 응용생물화학부) ;
  • 유성재 (충남대학교 농과대학 응용생물화학부) ;
  • 최경섭 (충남대학교 농과대학 응용생물화학부) ;
  • 김현제 ((주) 경농 경주연구소)
  • Published : 1998.12.30

Abstract

A series of bis-aromatic ${\alpha},{\beta}$-unsaturated ketone derivatives with mesaured fungicidal activities in vivo against rice blast(Pyricularia oryzae), tomato leaf blight (Phytophtora infestans) and barley powdery mildew(Erysiphe graminis) were studied by using quantitative structure activity relationship equations. The QSAR model for the activity of phenyl substituents, $1{\sim}11$, clearly reveals three important factors, namely, resonance(R<0), optimal molecular hydrophobicity(${\pi})_{opt.}=0.38$) and optimal distance($((L_{1})_{opt.}=5.69({\AA}))$ of substituent, respectively. But in case of 2-pyridyl substituents, $12{\sim}28$, the activity were governed by optimal molecular refractivity $((M_{R})_{opt.}=8.04{\sim}39cm^{3}/mol)$, steric effect(Es<0) and LUMO energy(e.v). The fungicidal activity relationship of phenyl and 2-pyridyl substituents against Erysiphe graminis have been proportioned.