Journal of the Korea Academia-Industrial cooperation Society (한국산학기술학회논문지)

The Korea Academia-Industrial cooperation Society (한국산학기술학회)
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Synthesis and Phytophathogenic Activities of Isopropylmethylphenyl benzenesulfonate Derivatives

Isopropylmethylphenyl benzenesulfonate 유도체의 합성과 식물병원균에 대한 생리활성

  • 최원식 (순천향대학교 생명공학과) ;
  • 남석우 (순천향대학교 생명공학과) ;
  • 김학천 (경보제약(주) 중앙연구소)
  • Received : 2010.10.06
  • Accepted : 2010.12.17
  • Published : 2010.12.31
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Abstract

Twenty five compounds isopropylmethylphenyl benzenesulfonate derivatives of thymol (1), 4-isopropyl-3-methylphenol (2), 5-isopropyl-3-methylphenol (3), 4-isopropylphenol (4), and 2-isopropylphenol (5) derivatives were synthesized. These compounds were analyzed for their structural confirmation with IR, GC/MS, and $^1H$-NMR. Synthetic compounds were tested against phytopathogenic fungi activities such as Pyrcularia grisea, Rhizoctonia solani, Phytophthora infestans, Colletotrichum orbiculare, and Sphaerotheca fusca. 2-Isopropyl-5-methylphenyl o-toluenesulfonate (1a), 2-isopropylphenyl 2,4,5-trichloro-benzenesulfonate (5b) and 2-isopropylphenyl 2-methyl-5-nitrobenzenesulfonate (5e) showed a potent in vivo antifungal activity against Pyrcularia grisea, Phytophthora infestans and Sphaerotheca fusca.

본 연구에서 thyme oil의 주성분인 thymol (1)과 유사한 구조를 갖는 4-isopropyl-3-methylphenol (2), 5-isopropyl-3-methylphenol (3), 4-isopropylphenol (4)과 2-isopropylphenol (5)을 출발 물질로 하여 sulfonyl ester 계열 유도체 25종을 합성하였다. IR, $^1H$-NMR과 GC/MS를 이용하여 이들 유도체들이 합성되었음을 확인하였다. 이들 유도체들에 대한 식물병원균의 생장 억제실험은 벼도열병균(Pyrcularia grisea), 벼잎집무늬마름병균(Rhizoctonia solani), 토마토잎마름역병균(Phytophthora infestans), 오이탄저병균(Colletotrichum orbiculare)과 오이흰가루병균(Sphaerotheca fusca)에 대하여 실시하였다. 그 결과, 2-isopropyl-5-methylphenyl o-toluenesulfonate (1a), 2-isopropylphenyl 2,4,5-trich lorobenzenesulfonate (5b)와 2-isopropylphenyl 2-methyl-5-nitrobenzenesulfonate (5e)는 각각 in vivo에서 벼도열병균(Pyrcularia grisea), 토마토잎마름역병균(Phytophthora infestans)과 오이흰가루병균(Sphaerotheca fusca)에 대하여 우수한 항균활성을 나타내었다.

Keywords

References

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