DOI QR코드

DOI QR Code

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

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.

Keywords

Isopropylmethylphenyl benzenesulfonate derivatives;Phytopathogen;Fungicidal activity

Acknowledgement

Supported by : 순천향대학교

References

  1. G. S. Helling, P. C. Kearney and M. Alexan, Behavior of pesticides in soil, Advan. Agron, 23, pp. 147-240, 1971. https://doi.org/10.1016/S0065-2113(08)60153-4
  2. A. W. Brown, A ecology of pesticides, John wiley, 1978.
  3. K. Hurele, Do soil suffer from pesticide?, In Pesticide Chemistry : IUPAC., (ed., Freshe, H., V. C. H, Verlagsgellschaft, MB, H. Weinheion). pp. 319-327, 1991.
  4. Y. Kurahashi, S. Sakawa, T. Kinbara, K.Tanaka and S. Kagabu, Biological activity of carpropamid (KTU 3616): A new fungicide for rice blast disease, J. Pesticide Sci, 22, pp. 108-112, 1997. https://doi.org/10.1584/jpestics.22.108
  5. S. E. Lee, B. S. Park, M. K. Kim, W. S. Choi, H. T. Kim, K. Y. Cho, S. G. Lee, and H. S. Lee, Fungicidal activity of pipernonaline, a piperidine alkaloid derived from long paper, Piper longum L., against phytopathogenic fungi, Crop Prot, 20, pp. 523-528, 2001a. https://doi.org/10.1016/S0261-2194(00)00172-1
  6. B. H. Lee, W. S. Choi, S. E. Lee, and B. S. Park, Fumigant toxicity of essential oils an their constituent compounds towards the rice weevil, Sitophilus oryzae (L.), Crop Prot, 20, pp. 317-320, 2001b. https://doi.org/10.1016/S0261-2194(00)00158-7
  7. B. Lawrence, Rosemary oil. Essential oils, USA Allured Publishing, pp. 60, 1989.
  8. Larrondo, J. V., M. Agut, and M. A. Torras, Antibacterial activity of essenes from labiates, Microbios, 82, pp. 171-172.
  9. G. N. Agrios, Significance of plant disease, In Plant Pathology (4th edition), Academic Press, San Diego, USA, pp. 25-37.
  10. P. Muller, Effect of pesticides of fauua and flora in pesticide, In Food and Environmental Implications, IAEA, Vienna.
  11. S. O. Duke, A. M. Rimando, S. R. Baerson, B. E. Scheffler, E. Ota, and R. G. Belz, Strategies for the use of natural products for weed managemet, J. Pesticide Sci, 2, pp. 298-306, 2002.
  12. B. H. Lee, C. P. Annis, F. Tumaalii, and W. S. Choi, Fumigant toxicity of essential oils from the Myrtaceae family and 1,8-cineole against 3 major stored-grain insects, J. Stored Prod. Res, 40, pp. 553-564, 2004. https://doi.org/10.1016/j.jspr.2003.09.001
  13. 최원식, 김관영, 장도연, 엄대용, 김태준, 정봉진, 식물오일과 그 성분들의 살균활성, 농약과학회지,10(3), pp. 201-209, 2006.
  14. 최원식, 정찬진, 장도연, 차경민, 엄대용, 김태준, 정봉진, Thymol과 Carvacrol 유도체들의 합성과 식물병원균에 대한 항균활성, 농약과학회지, 10(4), pp.237-248, 2006.
  15. 최원식, 장도연, 최경길, 이병호, 김태준, 정봉진, Isopropylphenyl 유도체들의 합성과 식물병원균에 대한 항균활성, J. Korean Soc. Appl. Biol. Chem, 50(3), pp. 178-186, 2007.
  16. 최원식, 장순호, 장도연, 최경길, 이병호, 김태준, 정봉진, 4-Isopropyl, 5-isopropyl-3-methylphenol 유도체들의 합성과 식물병원균에 대한 항균 활성, 농약과학회지, 10(4), pp. 249-261, 2006.
  17. 신승원, 수종허브 정유의 Candida속 진균에 대한 억제 활성 및 ketoconazole과의 병용효과, 대한약학회지, 46(3), pp. 203-207.