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Spirodiclofen Analogues as Potential Lipid Biosynthesis Inhibitors: A Convenient Synthesis, Biological Evaluation, and Structure-Activity Relationship

  • Ke, Shaoyong (Hubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Sciences) ;
  • Sun, Tingting (Hubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Sciences) ;
  • Zhang, Zhigang (Hubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Sciences) ;
  • Zhang, Ya-Ni (Hubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Sciences) ;
  • Liang, Ying (Hubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Sciences) ;
  • Wang, Kaimei (Hubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Sciences) ;
  • Yang, Ziwen (Hubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Sciences)
  • Received : 2010.02.08
  • Accepted : 2010.06.30
  • Published : 2010.08.20

Abstract

Twenty spirodiclofen analogues have been designed and conveniently synthesized via three steps including esterification, one-pot heterocyclization, and acylation reactions. The target molecules have been identified on the basis of analytical spectra ($^1H$ NMR, $^{13}C$ NMR and ESI-MS) data. All newly synthesized compounds have been screened for their potential insecticidal and herbicidal activity by standard method. The preliminary assays indicated that some of analogues displayed moderate to good insecticidal activity against Plutella xylostella compared with spirodiclofen, and some compounds showed obvious activity against Brassica chinensis. Structure-activity relationship (SAR) is also discussed based on the experimental data.

Keywords

References

  1. Wing, K. D.; Sacher, M.; Kagaya, Y.; Tsurubuchi, Y.; Mulderig, L.; Connair, M.; Schnee, M. Crop Prot. 2000, 19, 537. https://doi.org/10.1016/S0261-2194(00)00070-3
  2. Qian, X.; Lee, P. W.; Cao, S. J. Agric. Food Chem. 2010, 58, 2613. https://doi.org/10.1021/jf904098w
  3. Suzuki, J.; Ishida, T.; Kikuchi, Y.; Ito, Y.; Morikawa, C.; Tsukidate, Y.; Tanji, I.; Ota, Y.; Toda, K. J. Pestic. Sci. 2002, 27, 1. https://doi.org/10.1584/jpestics.27.1
  4. Fischer, R.; Bretschneider, T.; Krueger, B. W.; Bachmann, J.; Erdelen, C.; Wachendorff-Neumann, U.; Santel, H. J.; Luerssen, K.; Schmidt, R. R. DE 4216814, 1993.
  5. Wachendorff, U.; Brück, E.; Elbert, A.; Fischer, R.; Nauen, R.; Stumpf, N.; Tiemann, R. Proc. Brighton Crop Protection Conference - Pests & Diseases 2000, 2A-6, 53.
  6. Fischer, R.; Benet-Buchholz, J. Pflanzenschutz-Nachrichten Bayer 2002, 55, 137.
  7. Wachendorff, U.; Nauen, R.; Schnorbach, H. J.; Rauch, N.; Elbert, A. Pflanzenschutz-Nachrichten Bayer 2002, 55, 149.
  8. Chang, J.-Y.; Lu, K.-H.; Hsieh, T.-T. Plant Prot. Bull. 2007, 49, 187.
  9. Bretschneider, T.; Fischer, R.; Nauen, R. In Modern Crop Protection Compounds; Kramer, W., Schirmer, U. Eds.; Wiley-VCH Verlag GmbH & Co: Weinheim, Germany, pp 909-925, 2007.
  10. Nauen, R.; Bretschneider, T.; Elbert, A.; Fisher, R.; Tiemann, R. Pestic. Outlook 2003, 12, 243.
  11. Dekeyser, M. A. Pest Manag. Sci. 2005, 61, 103. https://doi.org/10.1002/ps.994
  12. Bretschneider, T.; Benet-Buchholz, J.; Fischer, R.; Nauen, R. Chimia 2003, 57, 697. https://doi.org/10.2533/000942903777678588
  13. Bretschneider, T.; Fischer, R.; Benet-Buchholz, J. Pflanzenschutz-Nachrichten Bayer 2005, 58, 307.
  14. Nauen, R.; Bretschneider, T.; Brueck, E.; Elbert, A.; Reckmann, U.; Wachendorff, U.; Tiemann, R. Proc. Brighton Crop Protection Conference - Pests & Diseases 2002, 2A-3, 39.
  15. Liu, T.-X. Crop Prot. 2004, 23, 505. https://doi.org/10.1016/j.cropro.2003.10.006
  16. Bielza, P.; Fernandez, E.; Grávalos, C.; Izquierdo, J. BioControl 2009, 54, 229. https://doi.org/10.1007/s10526-008-9162-0
  17. Fischer, R.; Himmler, T.; Nauen, R.; Reckmann, U.; Schmitt, W. Int. Plant Prot. Congress (IPPC), Glasgow, 2007; p 100.
  18. Van Waetermeulen, X.; Brück, E.; Elbert, A.; Fischer, R.; Krueger, S.; Kuhnhold, J.; Nauen, R.; Niebes, J. F.; Reckmann, U.; Schnorbach, H. J.; Steffens, R. Int. Plant Prot. Congress (IPPC), Glasgow, 2007; p 60.
  19. Nauen, R.; Bretschneider, T.; Elbert, A.; Fischer, R.; Reckmann, U.; van Waetermeulen, X. 11th IUPAC International Congress of Pesticide Chemistry, Aug 6-11. Kobe, Japan, 2006; p 109.
  20. Fischer, R.; Wei, H.-C. Bayer CropScience J. 2008, 61, 127.
  21. Bruck, E.; Elbert, A.; Fischer, R.; Krueger, S.; Kuhnhold, J.; Klueken, A. M.; Nauen, R.; Niebes, J. F.; Reckmann, U.; Schnorbach, H. J.; Steffens, R.; van Waetermeulen, X. Crop Prot. 2009, 28, 838. https://doi.org/10.1016/j.cropro.2009.06.015
  22. Van Pottelberge, S.; Van Leeuwen, T.; Khajehali, J.; Tirry, L. Pest Manag. Sci. 2009, 65, 358. https://doi.org/10.1002/ps.1698
  23. Nauen, R.; Stumpf, N.; Elbert, A. Proc. Brighton Crop Protection Conference - Pests & Diseases 2000, 4D-9, 453.
  24. Rauch, N.; Nauen, R. Pestic. Biochem. Phys. 2003, 74, 91.
  25. Nauen, R. J. Pestic. Sci. 2005, 30, 272. https://doi.org/10.1584/jpestics.30.272
  26. Van Pottelberge, S.; Khajehali, J.; Van Leeuwen, T.; Tirry, L. Exp. Appl. Acarol. 2009, 47, 301. https://doi.org/10.1007/s10493-008-9226-y
  27. Mallinger, A.; Le Gall, T.; Mioskowski, C. Synlett 2008, 386.
  28. Mallinger, A.; Le Gall, T.; Mioskowski, C. J. Org. Chem. 2009, 74, 1124. https://doi.org/10.1021/jo802038z
  29. Fischer, R.; Bretschneider, T.; Kruger, B. W.; Bachmann, J.; Erdelen, C.; Wachendorff-Neumann, U.; Santel, H. J.; Lurssen, K.; Schmidt, R. R. US 5262383, 1993.
  30. Fischer, R.; Lehr, S.; Feucht, D.; Losel, P.; Malsam, O.; Bojack, G.; Auler, T.; Hills, M. J.; Kehne, H.; Rosinger, C. H. WO 2005066125, 2005.
  31. Fischer, R.; Lehr, S.; Feucht, D.; Losel, P.; Malsam, O.; Bojack, G.; Auler, T.; Hills, M. J.; Kehne, H.; Rosinger, C. H. US 20070244007, 2007.
  32. Lu, Y.; Xu, X.; Sun, N.; Zhao, J. Fine Chem. Intermed. 2009, 39, 19.
  33. Zhao, J.; Ji, M.; Xu, X.; Cheng, J.; Zhu, G. Chin. Chem. Lett. 2009, 20, 1307. https://doi.org/10.1016/j.cclet.2009.06.028
  34. Zhao, J.; Zhou, Y.; Xu, X.; Cheng, J.; Zhu, G. Chin. J. Struct. Chem. 2009, 28, 837.
  35. FAO. Recommended methods for the detection and measurement of resistance of agricultural pests to pesticides: method for adult aphids; FAO method 17. FAO Plant Prot. Bull. 1979, 18, 6.
  36. Xue, S.; Ke, S.; Yan, L.; Cai, Z.; Wei, Y. J. Inorg. Biochem. 2005, 99, 2276. https://doi.org/10.1016/j.jinorgbio.2005.08.006

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