Pyridine and Thiazole-Containing Insecticides as Potent Agonists on Insect Nicotinic Acetylcholine Receptors

Bioactive Heterocyclic Compound Classes: Agrochemicals

Volumn , Issue , 2012, Pages 209-223

  Jeschke, Peter ^a  

^a BAYER CROPSCIENCE AG   (Germany)

Author keywords

Five membered ring system; Insecticidal activity; Neonicotinoid; Nicotinic acetylcholine receptor; Nithiazine; Nitromethylene; Pyridine; Thiazole

Indexed keywords

EID: 84883205983     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527664412.ch17     Document Type: Chapter

References (58)

1. Elbert, A., Overbeck, H., Iwaya, K., and Tsuboi, S. (1990) Proc. Brighton Crop Prot. Conf. - Pests Dis., 1, 21-28.
2. Jeschke, P., Moriya, K., Lantzsch, R., Seifert, H., Lindner, W., Jelich, K., Göhrt, A., Beck, M.E., and Etzel, W. (2001) Pflanzenschutz-Nachr. Bayer, 54, 147-160.
3. Minamida, I., Iwanaga, K., Tabuchi, T., Aoki, I., Fusaka, T., Ishizuka, H., and Okauchi, T. (1993) J. Pestic. Sci., 18, 41-48.
4. Takahashi, H., Mitsui, J., Takakusa, N., Matsuda, M., Yoneda, H., Suzuki, J., Ishimitsu, K., and Kishimoto, T. (1992) Proc. Brighton Crop Protect. Conf. - Pests Dis., 1, 89-96.
5. Babcock, J.M., Gerwick, C.B., Huang, J.X., Loso, M.R., Nakamura, G., Nolting, S.P., Rogers, R.B., Sparks, T.C., Thomas, J., Watson, G.B., and Zhu, Y. (2011) Pest Manage. Sci., 67, 328-334
6. Loso, M.R., Nugent, B.M., Huang, J.X., Rogers, R.B., Zhu, Y., Renga, J.M., Hegde, V.B., and Demark, J.J. (2007) WO2007/095229 (Dow AgroSciences LLC, USA), Priority Date Feb. 10 2006, Publication Date Aug. 23 2007.
7. Sparks, T.C., Loso, M.R., Watson, G.B., Babcock, J.M., Kramer, V.J., Zhu, Y., Nugent, M. and Thomas, J.D. (2012) in Modern Crop Protection Compounds (eds W. Krämer, U. Schirmer, P. Jeschke and M. Witschel) Wiley-VCH Verlag GmbH, Weinheim, pp. 1226-1237.
8. Senn, R., Hofer, D., Hoppe, T., Angst, W., Wyss, P., Brandl, F., Maienfisch, P., Zang, L., and White, S. (1998) Proc. Brighton Crop Prot. Conf.-Pests Dis., 1, 27-36.
9. Ohkawara, Y., Akayama, A., Matsuda, K., and Andersch, W. (2002) Proc. Brighton Crop Prot. Conf. - Pests Dis., 1, 51-58.
10. Nauen, R.R., Jeschke, P., and Copping, L. (2008) Pest Manage. Sci., 64, 1081
11. Jeschke, P. and Nauen, R. (2008) Pest Manage. Sci., 64, 1084-1098
12. Jeschke, P., Nauen, R., Schindler, M., and Elbert, A. (2011) J. Agric. Food Chem., 59, 2897-2908.
13. Feuer, H. and Lawrence, J.P. (1969) J. Am. Chem. Soc., 91, 1856-1857.
14. Soloway S.B., Henry, A.C., Kollmeyer W.D., Padgett, W.M., Powell, J.E.,Roman, S.A. Tieman, C.H., Corey, R.A., and Horne, C.A. (1978) in Pesticide and Venom Toxicology (eds D.L. Shankland, R.M. Hollingworth, and T. Smyth Jr.), Plenum, New York, pp. 153-158.
15. Kagabu, S. and Medej, S. (1995) Biosci. Biotechnol. Biochem., 59, 980-985.
16. Sone, S., Yamada, Y., and Tsuboi, S. (1995) Jpn. J. Appl. Entomol. Zool., 39, 171-173.
17. Kagabu, S. (1997) Rev. Toxicol., 1, 75-129
18. Kagabu, S. (2011) J. Agric. Food Chem., 59, 2887-2896.
19. Ohno, I., Tomizawa, M., Durkin, K.A., Naruse, Y., Casida, J., and Kagabu, S. (2009) Chem. Res. Toxicol., 22, 476-482
20. Tomizawa, M., Kagabu, S., and Casida, J.E. (2011) J. Agric. Food Chem., 59, 2918-2922.
21. Jeschke, P. (2007) in Insecticides Design Using Advanced Technologies (eds R. Nauen, A.R. Horowitz, and I. Ishaaya), Springer, Berlin, Heidelberg, pp. 151-195
22. Shao, X., Li, Z., Qian, Y., and Xu, X. (2009) J. Agric. Food Chem., 57, 951-957.
23. Zhu, Y., Loso, R.M., Watson, G.B., Sparks, T.C., Rogers, R.B., Huang, J.X., Gerwick, B.C., Babcock, J.M., Kelley, D., Hegde, V.B., Nugent, B.M., Renga, J.M., Denholm, I., Gorman, K., DeBoer, G.J., Hasler, J., Maede, T., and Thomas, J.D. (2011) J. Agric. Food Chem., 59, 2950-2957.
24. Jeschke, P., Schindler, M., Beck, M.E. (2002) Proc. Brighton Crop Prot. Conf. - Pests Dis., 1, 137-144
25. Jeschke, P. (2012) in Modern Crop Protection Compounds (eds W. Krämer, U. Schirmer, P. Jeschke and M. Witschel), Wiley-VCH Verlag GmbH, Weinheim, pp. 1169-1189
26. Jeschke, P., Moriya, K. (2012) in Modern Crop Protection Compounds (eds W. Krämer, U. Schirmer, P. Jeschke and M. Witschel), Wiley-VCH Verlag GmbH, Weinheim, pp. 1189-1203.
27. Maienfisch, P. (2012) in Modern Crop Protection Compounds (eds W. Krämer, U. Schirmer, P. Jeschke and M. Witschel), Wiley-VCH Verlag GmbH, Weinheim, pp. 1203-1224.
28. Matsuda, K., Buckingham, S.D., Kleier, D., Rauh, J.J., Grauso, M., and Sattelle, D.B. (2001) Trends Pharmacol. Sci., 22, 573-578
29. Tomizawa, M. and Casida, J.E. (2003) Annu. Rev. Entomol., 48, 339-364.
30. Jeschke, P. and Nauen, R. (2012) in Modern Crop Protection Compounds (eds W. Krämer, U. Schirmer, P. Jeschke and M. Witschel), Wiley-VCH Verlag GmbH, Weinheim, pp. 1127-1165.
31. Liu, M.-Y., Casida, J.E. (1993) Pestic. Biochem. Physiol., 46, 40-46
32. Liu, M.-Y., Lanford, J., and Casida, J.E. (1993) Pestic. Biochem. Physiol., 46, 200-206.
33. Nauen, R., Ebbinghaus-Kintscher, U., Salgado, V.L., and Kaussmann, M. (2003) Pest. Biochem. Physiol., 76, 55-69
34. Jeschke, P. and Nauen, R. (2007) in Synthesis and Chemistry of Agrochemicals VII, ACS Symposium Series, Vol. 948 (eds J.W. Lyga and G. Theodoridis), American Chemical Society, Washington, DC, pp. 51-65
35. Casida, J.E. (2011) J. Agric. Food Chem., 59, 2923-2931.
36. Benzidane, Y., Touinsi, S., Motte, E., Jadas-Hécart, A., Communal, P.-Y., Leduc, L., and Thany, S.H. (2010) Pest Manage. Sci., 66, 1351-1359
37. Kayser, H., Lee, C., Decock, A., Baur, M., Haettenschwiler, J., and Maienfisch, P. (2004) Pest Manage. Sci., 60, 945-958
38. Wellmann, H., Gomes, M., Lee, C., and Kayser, H. (2004) Pest Manage. Sci., 60, 959-970.
39. Karmakar, R. and Kulshrestha, G. (2009) Pest Manage. Sci., 65, 931-937.
40. Smit, A.B., Syed, N.I., Schaap, D., van Minnen, J., Klumperman, J., Kits, K.S., Lodder, H., van der Schors, R.C., van Elk, R., Sorgedrager, B., Brejc, K., Sixma, T.K., and Geraerts, W.P. (2001) Nature, 411, 26-268
41. Hansen, S.B., Talley, T.T., Radic, Z., and Taylor, P. (2004) J. Biol. Chem., 279, 24197-24202.
42. Talley, T.T., Harel, M., Hibbs, R.E., Radic, Z., Tomizawa, M., Casida, J.E., and Taylor, P. (2008) Proc. Nat. Acad. Sci. U.S.A., 105, 7606-7611
43. Ihara, M., Okajima, T., Yamashita, A., Oda, T., Hirata, K., Nishiwaki, H., Morimoto, T., Akamatsu, M.M., Ashiwaki, Y.Y., Kuroda, S., Mega, R., Kuramitsu, S., and Sattelle, D.B. (2008) Invertebrate Neuosci., 8, 71-81.
44. Denholm, I., Devine, G., Foster, S., Gorman, K., and Nauen, R. (2002) BCPC Pests Dis., 1, 161-168
45. Nauen, R., Denholm, I. (2005) Arch. Insect. Biochem. Physiol., 58, 200-215.
46. Elbert, A., Haas, M., Springer, B., Thielert, W., and Nauen, R. (2008) Pest Manage. Sci., 64, 1099-1105
47. Elbert, A., Nauen, R. (2004) in Insect Pest Management, Field and Protection Crops (eds A.R. Horowitz and I. Ishaaya), Springer, Berlin, pp. 29-44
48. Jeschke P. and Nauen, R. (2010) in Insect Control, Biological and Synthetic Agents (eds L.I. Gilbert and S.S. Gill), Academic Press, San Diego, CA, pp. 61-119.
49. Jeschke, P. (2012) in Modern Crop Protection Compounds (eds W. Krämer, U. Schirmer, P. Jeschke and M. Witschel), Wiley-VCH Verlag GmbH, Weinheim, pp. 1165-1169.
50. Kagabu, S. (2003) in Chemistry of Crop Protection: Progress and prospects in Science and Regulation (eds G. Voss and G. Ramos), Wiley-VCH Verlag GmbH, New York, pp. 193-212.
51. Akayama, A. and Minamida, I. (1999) in Neonicotinoid Insecticides and Nicotinic Acetylcholine Receptor (eds I. Yamamoto and J.E. Casida), Springer, New York, pp. 127-148.
52. Yamada, T., Takahashi, H., and Hatano, R. (1999) in Neonicotinoid Insecticides and Nicotinic Acetylcholine Receptor (eds I. Yamamoto and J.E. Casida), Springer, New York, pp. 149-175.
53. Jeschke, P. (2004) ChemBioChem, 5, 570-598.
54. Uneme, H. (2011) J. Agric. Food Chem., 59, 2932-2937.
55. Shao, X., Lee, P.W., Liu, Z., Xu, X., Li, Z., and Qian, X. (2011) J. Agric. Food Chem., 59, 2943-2949.
56. Fang, S., Zhang, B., Ren, K.-W., Cao, M.-M., Shi, H.-Y., and Wang, M.-H. (2011) J. Agric. Food. Chem., 59, 1594-1597
57. Wu, M., Xiao, J., Cai, J., Yao, J., Dai, B., and Lu, Y. (2010) Fresenius Environ. Bull., 19, 2582-2596.
58. Agranova (2009) AG Chem. New Comp. Rev., 27, 62.