Substituent Effect on the Fungicidal Activity of New N-substituted Benzotriazol-1-yl Derivatives

새로운 N-치환 benzotriazol-1-yl유도체의 항균활성에 미치는 치환기 효과

Series of new chiral N-substituted benzotriazol-1-yl derivatives were synthesized and their fungicidal activities in vitro against gray mold(Botrytis cinerea), black spot(Alternaria kikuchiana) and phytophthora blight(Phytophthora capsici) were measured by the agar medium dilution method. The substituents effects between the fungicidal activities (obs. $pI_{50}$) and a various physicochemical parameters of phenoxy or thiophenoxy group(X) & alkyl or phenyl group(Y) were analyzed by the multiple regression technique. From the analyzed substituent effects, the structure-activity relationship(SAR) equations shows that the antifungal activities depend on the parameters for the optimal molecular hydrophobicity($({\Sigma}logP)_{opt}$), Van der Waals (${\Sigma}Vw$>0) volume(${\AA}^3$) and inductive constant with electron withdrawing group(${\sigma}_I$,Y>0). The activity in affected by the inductive effect (${\sigma}_I$,Y>${\sigma}_g$X) of Y-group rather than the X-group. The phenoxy substituents, 1, showed higher antifungal activity tn the thiophenoxy substituents, 2. For 1, polar substituent constant(${\sigma}^*$) was an important factor in determining the activity. And the tribromomethyl substituent, 1g showed the highest activity against the tee fungi.

일련의 새로이 합성된 chira핀 N-치환 benzotriazol-1-yl유도체들의 구조와 잿빛 곰광이균(Botrytis cinerea), 배 검은 무늬병균(Alternaria kikchiana) 및 고추 역병균(Phytophthora capsici) 등 3종의 곰광이균류에 대한 항균활성에 미치는 치환기의 효과를 검토한 결과, 전자끌게(${\sigma}_I$,Y>0)로써 phenoxy 또는 thiophenoxy group(X) 보다는 alkyl또는 phenyl group(Y)이 더 큰 영향을 미쳤으며 phenoxy-치환체, 1이 thiophenoxy-치환체, 2보다 높은 항균활성을 나타내었다. 항균활성에 영향을 미치는 요인으로는 소수성(${\Sigma}logP$)과 유도효과(${\sigma}_I$,Y) 및 Van der Waals(${\Sigma}Vw$) 체적(${\AA}^3$) 등 이었으며 chiral성은 활성개선에 기여하지 못하였으나 tribromomethyl-치환체, 1g는 제일 큰 활성을 나타내는 화합물이었다.