할로겐 치환체를 활용한 친환경 농약설계 동향

The Design Pattern of Environment-friendly Agrochemicals by Using the Halogen Substituents

  • 한상빈 (한국과학기술정보연구원 Reseat 프로그램)
  • Han, Sang-Bin (Reseat Program, Korea Institute of Science and Technology Information)
  • 투고 : 2010.06.25
  • 심사 : 2010.07.26
  • 발행 : 2010.09.30

초록

키워드

참고문헌

  1. Adams, H., L. Cockroft, C. Guardigli, C. A. Hunter, K. R. Lawson and J. Perkins (2004) Experimental measurement of noncovalent interactions between halogens and aromatic rings. ChemBioChem 5:657-665. https://doi.org/10.1002/cbic.200400018
  2. Akagi, T. (1996) A new binding model for structurally diverse acetolactate synthase (ALS) inhibitors. Pestic Sci 47:309-318. https://doi.org/10.1002/(SICI)1096-9063(199608)47:4<309::AID-PS420>3.0.CO;2-4
  3. Bartlett, D. W., J. M. Clough, J. R. Godwin, A. A. Hall, M. Hamer and B. Parr-Dobrzanski (2002) The strobilurin fungicides. Pest Manag Sci 58:649-662. https://doi.org/10.1002/ps.520
  4. Berger, B. M., M. Muller and A. Eing (2002) Quantitative structure-transformation relationships of sulfonylurea herbicides. Pest Manag Sci 58:724-735. https://doi.org/10.1002/ps.519
  5. Bieseler, B., C. Fedtke, T. Neuefeind, W. Etzel, L. Prade and P. Reinemer (1997) Maize selectivity of FOE5043. Degradation of active ingredient by glutathione-S-transferases. Pflanzenschutz-Nachrichten Bayer (German Edition) 50: 117-140.
  6. Biffinger, J. C., H. W. Kim and S. G. DiMagno (2004) The polar hydrophobicity of fluorinated compounds. ChemBioChem 5:622-627. https://doi.org/10.1002/cbic.200300910
  7. Bohm, H. J., D. Banner, S. Bendels, M. Kansy, B. Kuhn and K. Muller (2004) Fluorine in medicinal chemistry. ChemBioChem 5:637-643. https://doi.org/10.1002/cbic.200301023
  8. Briggs, G., D. Mansfield, B. Moloney, S. Gary and T. Wegmann (2006) The discovery and chemistry of fluopicolide: a new standard for oomycetes disease control. Pflanzenschutz-Nachrichten Bayer 59:141-152.
  9. Davies, P. and M. Muncey (2004) Prothioconazole for control of Sclerotinia sclerotiorum in oilseed rape/canola. Pflanzenschutz-Nachrichten Bayer 57:283-293.
  10. Dunitz, J. D. (2004) Organic fluorine: odd man out. ChemBioChem 5:614-621. https://doi.org/10.1002/cbic.200300801
  11. Dutzmann, S. and A. Suty-Heinze (2004) Prothioconazole: a broad spectrum demethylation-inhibitor (DMI) for arable crops. Pflanzenschutz-Nachrichten Bayer 57:249-264.
  12. Dutzmann, S., H. Hayakawa, A. Oshima and A. Suty-Heinze (2004) Fluoxastrobin: the leaf-systemic, broad spectrum strobilurin. Pflanzenschutz-Nachrichten Bayer 57:415-435.
  13. Ebbinghaus, D., H. J. Schnorbach and A. Elbert (2007) Field development of flubendiamide (Belt., Fame, Fenos., Amoli.) - anewinsecticide for the control of lepidopterous pests. Pflanzenschutz-Nachrichten Bayer 60:219-246.
  14. Forster, H., H. H. Schmidt, H. J. Santel and R. Andree (1997) FOE 5043 - a new selective herbicide from oxyacetamide group. Pflanzenschutz-Nachrichten Bayer (German Edition) 50:105-116.
  15. Freigang, J., B. Laber, G. Lange and A. Schulz (2008) The biochemistry of pyrasulfotole. Pflanzenschutz-Nachrichten Bayer 61:15-28.
  16. Goto, T., A. Yanagi and Y. Watanabe (2007) Inhibition of cell division (oxyacetamides, tetrazolinones), in Modern Crop Protection Compounds, ed. by KramerW and Schirmer U. Wiley-VCH, Weinheim, Germany, pp. 325-334.
  17. Hamaguchi, H. and T. Hirooka (2007) Insecticides affecting calcium homeostasis - flubendiamide, in Modern Crop Protection Compounds, ed. by Kramer W and Schirmer U. Wiley-VCH, Weinheim, Germany, pp. 1121-1138.
  18. Hamprecht, G. and M. Witschel (2007) Phytoene desaturase inhibitors, in Modern Crop Protection Compounds, ed. by KramerW and Schirmer U. Wiley-VCH, Weinheim, Germary, pp. 187-211.
  19. Hauser-Hahn, I., P. Baur and W. Schmitt (2004) Fluoxastrobin (HEC 5725) - biochemistry and chemodynamic behaviour of a new leaf systemic strobilurin fungicide. Pflanzenschutz-Nachrichten Bayer 57:437-450.
  20. Hauser-Hahn, I., P. Baur and W. Schmitt (2004) Prothioconazole - a new dimension DMI. Biochemistry, mode of action, systemic effects. Pflanzenschutz-Nachrichten Bayer 57:237-248.
  21. Heinemann, U., J. Benet-Buchholz, W. Etzel and M. Schindler (2004) Fluoxastrobin (HEC 5725) - the new dimension in strobilurin fungicides. Pflanzenschutz-Nachrichten Bayer 57:299-318.
  22. Hirooka, T., T. Nishimatsu, H. Kodama, U. Reckmann and R. Nauen (2007) The biological profile of flubendiamide, a new benzenedicarboxamide insecticide. Pflanzenschutz-Nachrichten Bayer 60:183-203.
  23. Jeschke, P. (2004) The unique role of fluorine in the design of active ingredients for modern crop protection. ChemBioChem 5:570-589. https://doi.org/10.1002/cbic.200300833
  24. Jeschke, P. (2007) Nicotinic acetylcholine receptor agonists. Target and selectivity aspects, in Modern Crop Protection Compounds, ed. by KramerW and Schirmer U. Wiley-VCH, Weinheim, Germany, pp. 927-994.
  25. Jeschke, P. (2007) The unique role of halogen substituents in the design of modern crop protection compounds, in Modern Crop Protection Compounds, ed. by Kramer W and Schirmer U. Wiley-VCH, Weinheim, Germany, pp. 1189-1237.
  26. Jeschke, P. (2010) The unique role of halogen substituents in the design of modern agrochemicals. Pest Manag Sci 66:10-27. https://doi.org/10.1002/ps.1829
  27. Jeschke, P. and R. Nauen (2008) Neonicotinoids from zero to hero in insecticide chemistry. Pest Manag Sci 64:1084-1098. https://doi.org/10.1002/ps.1631
  28. Jeschke, P., E. Baston and F. R. Leroux (2007) $\alpha$-Fluorinated ethers as 'exotic' entity in medicinal chemistry. Mini-Reviews Med Chem 7:1027-1034. https://doi.org/10.2174/138955707782110150
  29. Kuck, K. H. and J. P. Vors (2007) Sterol biosynthesis inhibitors, in Modern Crop Protection Compounds, ed. by Kramer W and Schirmer U. Wiley-VCH, Weinheim, Germany, pp. 605 -650.
  30. Latorse, M. P., D. Holah and R. Bardsley (2006) Fungicidal properties of fluopicolide-based products. Pflanzenschutz-Nachrichten Bayer 59:185-200.
  31. Leroux, F. (2004) Atropisomerism, biphenyls, and fluorine: a comparison of rotational barriers and twist angles. ChemBioChem 5:644-649. https://doi.org/10.1002/cbic.200300906
  32. Leroux, F., B. Manteau, J. P. Vors and S. Pazenok (2008) Trifluoromethyl ethers - synthesis and properties of an unusual substituent. Beilstein J Org Chem 4:1-15.
  33. Maienfisch, P. and R. G. Hall (2004) The importance of fluorine in the life science industry. Chimia 58:93-99. https://doi.org/10.2533/000942904777678091
  34. Muller, K. H. (2007) Sulfonylaminocarbonyl-triazolinones, in Modern Crop Protection Compounds, ed. by Kramer W and Schirmer U. Wiley-VCH, Weinheim, Germany, pp. 138-151.
  35. Nauen, R., S. Konanz, T. Hirooka, T. Nishimatsu and H. Kodama (2007) Fluben-diamide a unique tool in resistance management tactics for pest lepidoptera difficult to control. Pflanzenschutz-Nachrichten Bayer 60:247-262.
  36. O'Hagan, D. (2008) Understanding organofluorine chemistry. An introduction to the C-F bond. Chem Soc Rev 37:308-319. https://doi.org/10.1039/b711844a
  37. Ort, H. (2007) Newer sulfonylureas, in Modern Crop Protection Compounds, ed. by Kramer Wand Schirmer U. Wiley-VCH, Weinheim, Germany, pp. 457-495.
  38. Purser, S., P. R. Moore, R. Peter, S. Swallow and V. Gouverneur (2008) Fluorine in medicinal chemistry. Chem Soc Rev 37:320-330. https://doi.org/10.1039/b610213c
  39. Sauter, H. (2007) Strobilurins and other complex III inhibitors, in Modern Crop Protection Compounds, ed. by Kramer W and Schirmer U. Wiley-VCH, Weinheim, Germany, pp. 457-495.
  40. Schmitt, M. H., A. van Almsick and L. Willms (2008) Discovery and chemistry of pyrasulfotole, a new dicot herbicide for cereal production. Pflanzenschutz-Nachrichten Bayer 61:7-14.
  41. Schulte, A. and H. Kocher (2008) The mode of action of pyrasulfotole. Pflanzenschutz-Nachrichten Bayer 61:29-42.
  42. Seebach, D. (1990) Organic synthesis - where next? Angew Chem Internat Ed Engl 29:1320-1367. https://doi.org/10.1002/anie.199013201
  43. Shimizu, M. and T. Hiyama (2005) Modem synthetic methods for fluorine substituted target molecules. Angew Chem Internat Ed 44:214-231. https://doi.org/10.1002/anie.200460441
  44. Soderlund, D. M. (2008) Pyrethroids, knockdown resistance and sodium channel. PestManag Sci 64:610-616.
  45. Suty-Heinze, A. and S. Dutzmann (2004) Fusarium head blight: an additional strength of prothioconazole. Pflanzenschutz-Nachrichten Bayer 57:265-282.
  46. Suty-Heinze, A., I. Hauser-Hahn and K. Kemper (2004) Prothioconazole and fluoxastrobin: two newmolecules for the use as seed treatment in cereals. Pflanzenschutz-Nachrichten Bayer 57:451-472.
  47. Thielert, W. (2006) A unique product: the story of the imidacloprid stress shield. Pflanzenschutz-Nachrichten Bayer 59:73-86.
  48. Thompson, M. E. (2007) Biochemistry of the target and resistance, in Modern Crop Protection Compounds, ed. by Kramer W and Schirmer U. Wiley-VCH, Weinheim, Germany, pp. 457-495.
  49. Tohnishi, M., H. Nakao, T. Furuya, A. Seo, H. Kodama and K. Tsubata (2005) Flubendiamide, a novel insecticide highly active against lepidopterous pests. J Pestic Sci 30:354-360. https://doi.org/10.1584/jpestics.30.354
  50. Toquin, V., F. Barja, C. Sirven, S. Gamet, M. P. Latorse and J. L. Zundel (2006) A new mode of action for fluopicolide: modification of the cellular localization of a spectrin-like protein. Pflanzenschutz-Nachrichten Bayer 59:171-184.
  51. Wakabayashi, K. and P. Boger (2002) Target sites for herbicides: entering the 21st century. PestManag Sci 58:1149-1154.
  52. Ziegler, H., J. Benet-Buchholz, W. Etzel and H. Gayer (2003) Trifloxystrobin - a new strobilurin fungicide with an outstanding biological activity. Pflanzenschutz-Nachrichten Bayer 56:213-230.