항균활성을 나타내는 thyme oil의 주성분인 thymol(I)과 carvacrol(II)을 출발물질로 하여 ester, sulfonyl ester, carbamate, ether와 phosphoyl ester 계열 유도체 41종을 합성하였다. IR, GC/MS 와 $^1H$-NMR spectrum을 이용하여 합성된 화합물들을 확인하였다. 이들 유도체들을 10종의 식물 병원균에 대하여 항균활성 실험을 실시한 결과 몇가지 화합물이 우수한 항균활성을 나타내었다. 이들 화합물에 대한 in vivo실험은 오이, 토마토와 벼 작물에서 실시하였다. 그 결과, 2-isopropyl-5-methylphenyl acetate(I-1a)가 오이 잿빛곰팡이 병균(Botrytis cinerea)과 벼도열병균(Pyrcularia oryzae)에 높은 항균활성을 나타내었으며, methyl(2-isopropyl-5-methylphenoxy)acetate(I-6d)는 벼 잎집무늬마름병균(Rhizoctonia solani)에서 ethyl4-(2-methyl5-isopropylphenoxy)-crotonate(I-7d)는 토마토역병균(Phytophthora infestans)에서 우수한 항균활성을 나타내었다.
Forty one compounds such as ester, sulfonyl ester, carbamate, ether and phosphoyl ester derivatives of thymol(I) and carvacrol(II) were synthesized. These derivatives were identified by IR, GC/MS and $^1H$-NMR spectra. Their antifungal activities were tested against various plant pathogenicfugi. Among them, several compounds were showed potent in vivo antifungal activities. The selected compounds showing in vitro antifungal activities were tested in vivo antifungal activities aganint 5 plant diseases such as rice blast, rice sheath blight, tomato late blight, cucumber anthracnose, and cucumber gray mold. As a result, 2-isopropyl-5-methylphenylacetate(I-1a) effectively suppressed the development cucumber gray mold and rice blast. Methyl(2-isopropyl-5-methylphenoxy)acetate(I-6d) and ethyl 4-(5-methyl-2-isopopylphenoxy)crotonate(I-7d) also showed potent in vivo antifungal actively againt rice sheath blight and tomato late blight, respectively.
