The Korean Journal of Pesticide Science (농약과학회지)

The Korean Society of Pesticide Science (한국농약과학회)
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A Synthesis of Alkylphenyl fluorobenzoate Derivatives and Their Antifungal Activities on Several Phytopathogens

Alkylphenyl fluorobenzoate 유도체들의 합성과 몇 가지 식물병원균에 대한 항균활성

  • 최원식 (순천향대학교 자연과학대학 생명공학과) ;
  • 차경민 (순천향대학교 자연과학대학 생명공학과) ;
  • 김영선 (순천향대학교 자연과학대학 생명공학과) ;
  • 장순호 (순천향대학교 자연과학대학 생명공학과) ;
  • 임상호 (남양유업(주) 중앙연구소) ;
  • 최인영 ((주)동부하이텍 농생명연구소) ;
  • 김태준 ((주)동부하이텍 농생명연구소) ;
  • 정봉진 ((주)동부하이텍 농생명연구소)
  • Published : 2008.12.31
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Abstract

Sixty compounds such as alkylphenyl fluorobenzoate esters from thymol(I), 5-isopropyl-3-methylphenol (II), 4-isopropyl-3-methylphenol (III), 2-sec-butylphenol (IV) and 4-sec-butylphenol (V) were synthesized. These derivatives were identified by IR, $^1H$-NMR spectrometer and GC/MS. Their in vivo antifungal activities were tested against phytopathogens such as Phytophthora infestans, Botrytis cinerea, Colletotrichum orbiculare and Rhizoctonia solani. As the result, 2-sec-butylphenyl 2,5-difluorobenzoate (IV-6) and 4-sec-butylphenyl 2,5-difluorobenzoate (V-6) showed 90% above antifungal activity against Botrytis cinerea. 2-Isopropyl-5-methylphenyl 2,3,6-trifluorobenzoate (I-11), 2-isopropyl-5-methylphenyl 2,4,5-trifluorobenzoate (I-12), 5-isopropyl-3-methylphenyl 2,3,6-trifluorobenzoate (II-11), 4-isopropyl-3-methylphenyl 2,3,6-trifluorobenzoate (III-11) and 4-isopropyl-3-methylphenyl 2,4,5-trifluorobenzoate (III -12) showed 90% above potent antifungal activity against Colletotrichum orbiculare.

Thymol(I), 5-isopropyl-3-methylphenol(II), 4-isopropyl-3-methylphenol(III), 2-sec-butylphenol(IV)과 4-sec-butylphenol(V)을 출발물질로 하여 alkylphenyl fluorobenzoate계 ester 유도체 60종을 합성하였다. 이 유도체들의 합성은 IR, $^1H$-NMR과 GC/MS를 이용하여 확인하였다. 이들 화합물들에 대하여 토마토 역병균, 오이 잿빛곰팡이병균, 오이 탄저병균과 벼 잎집무늬마름병균에 대한 항균활성을 조사하였다. 오이 잿빛곰팡이병균에 2-sec-butylphenyl 2,5-difluorobenzoate (IV-6)와 4-sec-butylphenyl 2,5-difluorobenzoate(V-6)등이 90% 이상의 우수한 항균활성을 나타내었다. 오이 탄저병균에 대하여 2-isopropyl-5-methylphenyl 2,3,6-trifluorobenzoate(I-11), 2-isopropyl-5-methylphenyl 2,4,5-trifluorobenzoate(I-12), 5-isopropyl-3-methylphenyl 2,3,6-trifluorobenzoate(II-11), 4-isopropyl-3-methylphenyl 2,3,6-trifluorobenzoate(III-11)와 4-isopropyl-3-methylphenyl 2,4,5-trifluorobenzoate(III-12)가 90% 이상의 매우 우수한 항균활성을 나타내었다.

Keywords

References

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