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.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
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.
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.
Shiokawa, K., Tsuboi, S., Kagabu, S., and Moriya, K. (1986) Jpn. Kokai Tokkyo Koho JP 61, 267–575.
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.
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.
Tomizawa, M. and Yamamoto, I. (1993) Structure-activity relationships of nicotinoids and Imidacloprid analogs. J. Pesticide Sci. 18, 91–98.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Moser, V. C. (1989). Screening approaches to neurotoxicity: A functional observational battery. J. Am. Coll. Toxicol. 8, 85–93.
Leicht, W. (1993). Imidacloprid: a chloronicotinyl insecticide. Pestic. Outlook 4, 17–21.
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2002 Springer Science+Business Media New York
About this chapter
Cite this chapter
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
Download citation
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
eBook Packages: Springer Book Archive