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

비스 방향족 ${\alpha},{\beta}$-불포화 케톤 유도체 중 2-thienyl 및 2-furyl 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) ;
  • Kim, Tae-Young (Division of Applied Biology & Chemistry, Chung-nam National University) ;
  • Ok, Whan-Suk (Mi-Sung LTD)
  • 성낙도 (충남대학교 농과대학 응용생물화학부) ;
  • 유성재 (충남대학교 농과대학 응용생물화학부) ;
  • 김태영 (충남대학교 농과대학 응용생물화학부) ;
  • 옥환석 (미성농약(주) 중앙연구소)
  • Published : 1998.09.30

Abstract

Twenty six derivatives of bis-aromatic ${\alpha},{\beta}$-unsaturated ketones as substrate(S) were synthesized and their fungicidal activities in vivo against rice blast(Pyricularia oryzae), tomato leaf blight(Phytophtora infestans) and barley powdery mildew(Erysiphe graminis) were examined. The quantitative structure-activity relationship(QSAR) between the fungicidal activities($pI_{50}$) and a physicochemical parameters of substitued($R_{2}$) phenyl backbone group in 2-thienyl and 2-furyl substituents were analyzed with regression equations. The activities of substituted($R_{2}$) phenyl backbone in 2-thienyl substituents, $1{\sim}10$ would depend largely on the resonance(R>0), molecular refractivity($M_{R}<0$) and optimal length of substituent(($L_{1})opt.=5.50{\AA}$). Whereas, in case of 2-furyl substituents, $10{\sim}26$ optimal molar attraction constant ($F_{opt}=0.49{\sim}l.11$), optimal steric($Es_{opt}=1.78$) constant and indicator variables(Io & Ip) for position of substituents. The fungicidal activity relationship of 2-thienyl substituents against Pyricularia oryzae and Phytophtora infestans have been a reciprocal proportioned.