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The Neonicotinoid Insecticides

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Handbook of Neurotoxicology
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Abstract

The neonicotinoid insecticides are a new generation of chemical agents that have recently been developed for commercial use. Their history can be traced to the late 1970s, when chemists at Shell Chemical Company investigated the heterocyclic nitromethylenes as potential insecticides (1,2). This research led to the discovery of nithiazine (WL 35651) (Fig. 1), which is the only representative of the early type of heterocyclic nitromethylene that has been registered for use as an insecticide. Poor photostability generally limits commercial applications for nithiazine and related (i.e., nitromethylene) compounds.

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References

  1. Soloway, S. B., Henry, A. C., Kollmeyer, W. D., Padgett, W. M., Powell, J. E., Roman, S. A., et al. (1978) Nitromethylene insecticides. Adv. Pestic. Sci. 4, 206–217.

    Google Scholar 

  2. Schroeder, M. E. and Flattum R. F. (1984) The mode of action and neurotoxic properties of the nitromethylene heterocycle insecticides. Pest. Biochem. Physiol. 22, 148–160.

    Article  CAS  Google Scholar 

  3. Shiokawa, K., Tsuboi, S., Kagabu, S., and Moriya, K. (1986) Jpn. Kokai Tokkyo Koho JP 61, 267–575.

    Google Scholar 

  4. Takahashi, H., Mitsui, J., Takakusa, N., Matsuda, M., Yoneda, H., Suzuki, J., Ishimitsu, K., and Kishmoto, T. (1992) NI-25, a new type of systemic and broad spectrum insecticide. Brighton Crop Protection Conferences — Pest and Diseases 1, 89–96.

    Google Scholar 

  5. Minamida, I., Iwanaga, K., Tabuchi, T., Aoki, I., Fusaka, T., Ishizuka, H., and Okauchi, T. (1993) Synthesis and insecticidal activity of acyclic nitroethene compounds containing a heteroarylmethylamino group. J. Pesticide Sci. 18, 41.

    Article  Google Scholar 

  6. Tomizawa, M. and Yamamoto, I. (1993) Structure-activity relationships of nicotinoids and Imidacloprid analogs. J. Pesticide Sci. 18, 91–98.

    Article  Google Scholar 

  7. Liu, M.-Y., Lanford, J., and Casida, J. E. (1993) Relevance of [3H]Imidacloprid binding site in house fly head acetylcholine receptor to insecticidal activity of 2-nitromethyleneand 2-nitroimino-imidazolidines. Pestic. Biochem. Physiol. 46, 200–206.

    Article  CAS  Google Scholar 

  8. Maienfisch, P., Brandl, F., Kobel, W., Rindlisbacher, A., and Senn, R. (1999) CGA 293’343: A novel, broad-spectrum neonicotinoid insecticide, in Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor ( Yamamoto, I. and Casida, J., eds.), Springer-Verlag, Tokyo, Japan, pp. 177–209.

    Chapter  Google Scholar 

  9. Chao, S. L. and Casida, J. E. (1997) Interaction of imidacloprid metabolites and analogs with the nicotinic acetylcholine receptor of mouse brain in relation to toxicity. Pest. Biochem. Physiol. 58, 77–88.

    Article  CAS  Google Scholar 

  10. Tomizawa, M., Latli, B., and Casida, J. E. (1999). Structure and function of insect nicotinic acetylcholine receptors studied with nicotinoid insecticide affinity probes, in Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor (Yamamoto, 1. and Casida, J., eds.), Springer-Verlag, Tokyo, Japan, pp. 271–292.

    Google Scholar 

  11. Nagata, K., Song, J. H., Shono, T., and Narahashi, T. (1998). Modulation of the neuronal nicotinic acetylcholine receptor-channel by the nitromethylene heterocycle Imidacloprid. J. Pharmacol. Exp. Ther. 285, 731–738.

    PubMed  CAS  Google Scholar 

  12. Tomizawa, M. and Casida, J. E. (1999) Minor structural changes in nicotinoid insecticides confer differential subtype selectivity for mammalian nicotinic acetylcholine receptors. Br. J. Pharmacol. 127, 115–122.

    Article  PubMed  CAS  Google Scholar 

  13. Liu, M.-Y. and Casida, J.E. (1993) High affinity binding of [3H]Imidacloprid in the insect acetylcholine receptor. Pestic. Biochem. Physiol. 46, 40–46.

    Article  CAS  Google Scholar 

  14. Tomizawa, M., Otsuka, H., Miyamoto, T., and Yamamoto, I. (1995) Pharmacological effects of Imidacloprid and its related compounds on the nicotinic acetylcholine receptor with its ion channel from the Torpedo electric organ. J. Pesticide Sci. 20, 49–56.

    Article  CAS  Google Scholar 

  15. Yamamoto, I., Yabuta, G., Tomizawa, M., Saito, T., Miyamoto, T., and Kagabu, S. (1995) Molecular mechanism for selective toxicity of nicotinoids and neonicotinoids. J. Pesticide Sci. 20, 33–40.

    Article  CAS  Google Scholar 

  16. Zwart, R., Oortgiesen, M., and Vijverberg, H. P. M. (1992). The nitromethylene heterocycle 1-(pyridin-3-yl-methyl)-2-nitromethylene-imidazolidine distinguishes mammalian from insect nicotinic receptor subtypes. Eur. J. Pharmacol. 228, 165–169.

    PubMed  CAS  Google Scholar 

  17. Zwart, R., Oortgiesen, M., and Vijverberg, H. P. M. (1994). Nitromethylene heterocycles: selective agonists of nicotinic receptors in locust neurons compared to mouse N1E-115 and BC3H1 cells. Pestic. Biochem. Physiol. 48, 202–213.

    Article  Google Scholar 

  18. Yamamoto, I., Tomizawa, M., Saito, T., Miyamoto, T., Walcott, E. C., and Sumikawa, K. (1998) Structural factors contributing to insecticidal and selective actions of neonicotinoids. Arch. Insect Biochem. Physiol. 37, 24–32.

    Article  PubMed  CAS  Google Scholar 

  19. Matsuda, K., Buckingham, S. D., Freeman, J. C., Squire, M. D., Baylis, H. A., and Sattelle, D. B. (1998) Effects of the alpha subunit on Imidacloprid sensitivity of recombinant nicotinic acetylcholine receptors. Br. J. Pharmacol. 123, 518–524.

    Article  PubMed  CAS  Google Scholar 

  20. Yamada, T., Takashi, H., and Hatano, R. (1999). A novel insecticide, Acetamiprid, in Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor ( Yamamoto, I. and Casida, J., eds.), Springer-Verlag, Tokyo, Japan, pp. 149–176.

    Chapter  Google Scholar 

  21. Akayama, A. and Minamida, I. (1999) Discovery of a new systemic insecticide, nitenpyram and its insecticidal properties, in Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor ( Yamamoto, I. and Casida, J., eds.), Springer-Verlag, Tokyo, Japan, pp. 127–148.

    Chapter  Google Scholar 

  22. Thyssen, J. and Machemer, L. (1999) Imidacloprid: toxicology and metabolism, in Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor ( Yamamoto, I. and Casida, J., eds.), Springer-Verlag, Tokyo, Japan, pp. 213–222.

    Chapter  Google Scholar 

  23. Moser, V. C. (1989). Screening approaches to neurotoxicity: A functional observational battery. J. Am. Coll. Toxicol. 8, 85–93.

    Article  CAS  Google Scholar 

  24. Leicht, W. (1993). Imidacloprid: a chloronicotinyl insecticide. Pestic. Outlook 4, 17–21.

    CAS  Google Scholar 

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Sheets, L.P. (2002). The Neonicotinoid Insecticides. In: Massaro, E.J. (eds) Handbook of Neurotoxicology. Humana Press, Totowa, NJ. https://doi.org/10.1007/978-1-59259-132-9_6

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  • DOI: https://doi.org/10.1007/978-1-59259-132-9_6

  • Publisher Name: Humana Press, Totowa, NJ

  • Print ISBN: 978-1-61737-193-6

  • Online ISBN: 978-1-59259-132-9

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