4-Isopropyl, 5-isopropyl-3-methylphenol 유도체들의 합성과 식물 병원균에 대한 항균 활성

Fifty compounds such as ester, sulfonyl ester, carbamate, ether and phosphoyl ester derivatives of 4-isopropyl-3-methylphenol(I) and 5-isopropyl-3-methylphenol(II) were synthesized. These derivatives were identified by IR, GC/MS and $^1H$-NMR spectra. Their in vitro antifungal activities were tested against 10 plant pathogenic fungi. Among them, several compounds showed potent in vitro antifungal activity. The selected compounds showing potent in vitro antifungal activity were tested for their in vivo antifungal activities against 5 plant diseases such as rice blast, rice sheath blast, cucumber anthracnose, cucumber gray mold and tomato late blight. As a result, 4-isopropyl-3-methylphenyl(2-amino-thiazole-4-yl)methoxyiminoacetate(I-7a) showed a potent in vivo antifungal activity against rice blast. Both methyl (4-isopropyl-3-methylphenoxy)acetate(I-4d) and methyl (5-isopropyl-3-methylphenoxy)acetate(II-4d) effectively inhibited the development of cucumber gray mold. 살균활성이 있는 4-isopropyl-3-methylphenol(I)과 5-isopropyl-3-methylphenol(II)을 출발물질로 하여 ester, sulfonyl ester, carbamate, ether 및 phosphoyl ester계열의 50개 화합물들을 합성하였으며, IR, GC/MS와 $^1H$-NMR spectrum을 이용하여 합성을 확인하였다. 이 유도체들에 대한 in vitro 살균활성 실험을 10종의 식물병원균에 대하여 실시한 결과 몇 가지 화합물이 우수한 항균활성을 나타내었다. 이들 화합물을 5가지 식물병(벼도열병, 토마토역병, 오이 잿빛곰팡이병, 벼 잎집무늬 마름병, 오이탄저병)에 대하여 in vivo 항균활성을 조사하였다. 그 결과, 4-isopropyl-3-methylphenyl (2-aminothiazole-4-yl)methoxyiminoacetate(I-7a)는 벼 도열병(Pycularia oryzae)에 methyl (4-isopropyl-3-methylphenoxy)acetate(I-4d)와 methyl (5-isopropyl-3-methylphenoxy) acetate (II-4d)는 오이 잿빛곰팡이병(Botrytis cinerea)에 높은 방제활성을 나타내었다.