The Korean Journal of Pesticide Science (농약과학회지)

The Korean Society of Pesticide Science (한국농약과학회)
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In vitro and in vivo antifunal activaties of derivatives of thymol( I ) and carvacrol(II) againt phytopathogenic fungi

Thymol과 Carvacrol 유도체들의 합성과 식물병원균에 대한 항균활성

  • Choi, Won-Sik (Department of Genetic Engineering, Soonchunhyang University) ;
  • Jung, Chan-Jin (Department of Genetic Engineering, Soonchunhyang University) ;
  • Jang, Do-Yun (Department of Genetic Engineering, Soonchunhyang University) ;
  • Cha, Kyoung-Min (Department of Genetic Engineering, Soonchunhyang University) ;
  • Um, Dae-Yong (Dongbu Advanced Research Institute) ;
  • Kim, Tae-Jun (Dongbu Advanced Research Institute) ;
  • Jung, Bong-Jin (Dongbu Advanced Research Institute)
  • 최원식 (순천향대학교 자연과학대학 유전공학과) ;
  • 정찬진 (순천향대학교 자연과학대학 유전공학과) ;
  • 장도연 (순천향대학교 자연과학대학 유전공학과) ;
  • 차경민 (순천향대학교 자연과학대학 유전공학과) ;
  • 엄대용 (동부기술원 농생명 연구소) ;
  • 김태준 (동부기술원 농생명 연구소) ;
  • 정봉진 (동부기술원 농생명 연구소)
  • Published : 2006.12.30
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Abstract

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.

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.

Keywords

References

  1. Agrios, G. N. (1997) Significance of plant disease pp.25-37 In Plant Pathology, (4th edition), Academic Press, San Diego, USA
  2. Brown, A. W. (1978) A ecology of pesticides., John wiley & sons
  3. Duke, S. O., A. M. Rimando, S. R. Baerson, B. E. Scheffler, E. Ota and R. G. Belz (2002) Strategies for the use of natural products for weed management. J. Pesticide Sci. 27:298-306 https://doi.org/10.1584/jpestics.27.298
  4. Helling, G. S., P. C. Kearney and M. Alexan (1971) Behavior of pesticides in soils. Advan. Agron. 23:147-240 https://doi.org/10.1016/S0065-2113(08)60153-4
  5. Hurele, K. (1991) Do soil suffer from pesticide? pp.319-327 In Pesticide Chemistry : IUPAC., (ed., Freshe, H., V. C. H, Verlagsgellschaft, MB, H. Weinheion)
  6. Kurahashi, Y., S. Sakawa, T. Kinbara, K. Tanaka and S. Kagabu (1997) Biological activity of carpropamid (KTU 3616): A new fungitide for rice blast disease. J. Pesticide Sci. 22: 108 - 112 https://doi.org/10.1584/jpestics.22.108
  7. Larrondo, J. V., M. Agut, and M. A. Torras (1995) Antibacterial activity of essenes from labiates. Microbios. 82: 171 - 172
  8. Lawrence, B. (1989) Rosemary oil. Essential oils 1981-1987 USA Allured Publishing, pp.60
  9. Lee, B. H., C. P. Annis, F. Tumaalii, and W. S. Choi (2004) Fumigant toxicity of essential oils from the Myrtaceae family and 1,8-cineole against 3 major stored-grain insects, J. Stored Prod. Res. 40:553 - 564 https://doi.org/10.1016/j.jspr.2003.09.001
  10. Lee, S. E., B. S. Park, M. K. Kim, W. S. Choi, H. T. Kim, K. Y. Cho, S. G. Lee, and H. S. Lee (2001a) Fungicidal activity of pipemonaline, a piperidine alkaloid derived from long paper, Piper longum L., against phytopathogenic fungi. Crop Prot. 20:523 - 528 https://doi.org/10.1016/S0261-2194(00)00172-1
  11. Lee, B. H., W. S. Choi, S. E. Lee, and B. S. Park (2001b) Fumigant toxicity of essential oils and their constituent compounds towards the rice weevil, Sitophilus oryzae (L.). Crop Prot. 20:317 - 320 https://doi.org/10.1016/S0261-2194(00)00158-7
  12. Muller, P. (1998) Effects of pesticides of fauua and flora in pestcide., pp.11-27. In Food and Environmental Implications, IAEA., Vienna
  13. 신승원 (2002) 수종허브 정유의 Candida속 진균에 대한 억제 활성 및 Ketoconazole과의 병용효과. 대한약학회지 46(3):203-207
  14. 최원식, 김관영, 장도연, 엄대용, 김태준, 정봉진 (2006) 식물오일과 그 성분들의 살균활성, 농약과학회지 10(3):201-209