Abstract
In the early 1980s, an important discovery was made by Shell researchers when the insecticidal activity of heterocyclic nitromethylene compounds was found (Soloway et al. 1979). After an intensive optimization program, Nithiazin was identified as the most active compound (Figure 1). However, this product was not commercialized. This new chemical class subsequently attracted much attention as a potential tool for insect control, and was taken up by several companies such as Bayer, Takeda, Nippon Soda, Agro Kanesho, Mitsui Toastu and Ciba (since 1996; Novartis).
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
Bai D, Lummis SCR, Leicht W, et al (1991) Actions of imidacloprid and related nitromethylene on cholinergic receptors of an identified insect motor neurone. Pestic Sci 33:197–204
Beck G, Heitzer H (1986) Manufacture of 2-chloro-5-(chloromethyl)thiazole. Ger Offen, DE 3631538 Al 880324
Benson JA (1989) Insect nicotinic acetylcholine receptors as targets for insecticides. BCPC Monogr. 43 (Prog. Prospects Insect Control), pp 59–70
Brandl F, Moore S, Fougeroux A (1997) CGA 293’343-a novel insecticide for the growing needs of the global seed treatment market. 1997 Annual Meeting of the Entomological Society of America, paper no 499
Elbert A, Overbeck H, Iwaya K, Tsuboi S (1990) Imidacloprid, a novel systemic nitromethylene analogue insecticide for crop protection. Brighton Crop Protection Conferences-Pest and Diseases 1, pp 21–28
Gsell L (1987a) Preparation and testing of [(pyridylmethyl)amino]nitroethylenes as insecticides, acaricides, and ectoparasiticides. Eur Pat Appl EP 302833 A2 890208
Gsell L (1987b) Preparation of pyridylmethylcyanoguanidines as insecticides and acaricides. Eur Pat Appl EP 306696 Al 890315
Kagabu S, Moriya K, Shibuya K, et al (1992) l-(6-Halonicotinyl)-2-nitromethylene-imidazolidines as potential new insecticides. Biosci Biotechnol Biochem 56:362–363
Kobel W, Tally A, Thede B (1997) CGA 293’343-a novel broad spectrum insecticide: safety aspects. 1997 Annual Meeting of the Entomological Society of America, paper no 497
Kxistiansen O, Maienfisch P, Gsell L (1989) Guanidine derivatives as insecticides. Eur Pat Appl EP 418199 A2 910320
Lawson DS, Bridges T, Ferguson S, et al (1997) CGA 293’343: a new insecticide from Novartis Crop Protection, for use from the ground up. 1997 Annual Meeting of the Entomological Society of America, paper no 498
Liu M-YJ, Cassida JE (1993) High affinity binding of 3H-imidacloprid in the insect acetylcholine receptor. Pestic Biochem Physiol 46:40–46
Liu M-YJ, Lanford J, Cassida JE (1993) Relevance of 3H-imidacloprid binding site in house fly head acetylcholine receptor to insecticidal activity of 2-nitromethylene-and 2-nitroimino-imidazolidines. Pestic Biochem Physiol 46:200–206
Maienfisch P, Gsell L (1992) Preparation of 3-(heterocyclylmethyl)-4-iminoperhydro-1,3,5-oxadiazine derivatives as pesticides. Eur Pat Appi EP 580553 A2 940126
Maienfisch P, Gonda J, Jacob O, Gsell L (1993) Novel 2-nitromethylidene/2-cyanimino/2-nitroimino-pyrrolidines and-piperidines, intermediates, and their use as pesticides. PCT Int Appl WO 9424124 Al 941027
Maienfisch P, Gonda J, Jacob O, et al (1997a) Synthesis and insecticidal activity of novel nicotinoids. Abstracts, 214th ACS National Meeting, Las Vegas, NV, September 7-11, 1997, AGRO-018. American Chemical Society, Washington, DC
Maienfisch P, Gsell L, Rindlisbacher A, Allemann D (1997b) CGA 293’343-a novel broad spectrum insecticide: chemistry and biological laboratory evaluation. 1997 Annual Meeting of the Entomological Society of America, paper no 495
McKay AF, Wright GF (1947) Preparation and properties of N-methyl-N-nitroso-N’-nitroguanidine. J Am Chem Soc 69:3028–3030
Minamida I, Iwanaga K, Okauchi T (1987) Alpha-unsaturated amines, their production and use. Eur Pat Appl EP 302389 A2 88112210.5
Minamida I, Iwanaga K, Tabuchi T et al, (1993a) Synthesis and insecticidal activity of acyclic nitroethene compounds containing a heteroarymethylamino group. J Pesticide Sci 18:41–48
Minamida I, Iwanaga K, Tabuchi T, et al (1993b) Synthesis and insecticidal activity of acyclic nitroethene compounds containing a 3-pyridylmethylamino group. J Pestic Sci 18:31–40
Moriya K, Shibuya K, Hattori Y, et al (1992) 1-(6-Halonicotinyl)-2-nitroimino-imidazolidines and related compounds as potential new insecticides. Biosci Biotechnol Biochem 56:364–365
Moriya K, Shibuya K, Hattori Y, et al (1993) l-Diazinylmethyl-2-nitromethylene-and 2-nitroimino-imidazolidines as potential new insecticides. J Pestic Sci 18:119–123
Morton HV, Moore S, Ngo N (1997) CGA 293’343: a new molecule for seed-delivered insect control in U.S. field crops. Annual Meeting of the Entomological Society of America, paper no 500
Rindlisbacher A, Buholzer H, Stöcklin P, Reiner W (1997) CGA 293’343 seed treatment activity in lab and greenhouse trials. 1997 Annual Meeting of the Entomological Society of America, poster no D1 84
Sattelle DB, Buckingham SD, Wafford KA, et al (1989) Actions of the insecticide 2-(nitromethylene)tetrahydro-l,3-thiazine on insect and vertebrate nicotinic acetylcholine receptors. Proc R Soc London (Biol) 237:501–514
Senn R, Tally A, FlÜckiger C, Hashino Y (1997) CGA 293*343-a novel broad spectrum insecticide: global field performance. 1997 Annual Meeting of the Entomological Society of America, paper no 496
Shiokawa K, Tsuboi S, Moriya K, et al (1988) Insecticidally active nitro compounds. Eur Pat Appl EP 375907 Al 891211180.7
Shiokawa K, Tsuboi S, Moriya K, Kagabu S (1995) Chloronicotinyl insecticides: development of imidacloprid. In: Ragsdale NN, Kearney PC, Plimmer JR (Eds) Eight International Congress of Pesticide Chemistry-Option 2000, ACS Conference Proceeding Series, pp 49–59
Shiokawa K, Tsuboi S, Iwaya K, Moriya K (1994) Development of a chloronicotinyl insecticide, imidacloprid. Nippon Noyaku Gakkaishi 19:209–217; 329-332
Soloway SB, Henry AC, Kollmeyer WD, et al (1979) Nitromethylene insecticides. In: Geissbiihler H, Brooks GT, Kearney PC (Eds) Advances in pesticide science, part 2. Pergamon Press, New York, pp 206–227
Steinemann A, Lawson S (1997) Uptake and translocation of CGA 293*343. 1997 Annual Meeting of the Entomological Society of America, poster no Dl 85
Tabuchi T, Fusaka T, Iwanaga K, et al (1994) Synthesis and insecticidal activity of acyclic nitroethene compounds containing (6-substituted)-3-pyridylamino group. J Pestic Sci 19:119–125
Takahashi H, Mitsui J, Takakusa N, et al (1992) NI-25, a new type of systemic and broad spectrum insecticide. Brighton Crop Protection Conferences-Pest and Diseases 1, pp 89–96
Tomizawa M (1994) Structure-activity relationships relationships of nicotinoids and the related compounds. J Pestic Sci 19:229–240
Tomizawa M, Yamamoto I (1992) Binding of nicotinoids and related compounds to the insect nicotinic acethylcholine receptor. J Pestic Sci 17:231–236
Tomizawa M, Yamamoto I (1993) Structure-activity relationships of nicotinoids and imidacloprid analogs. J Pestic Sci 18:91–98
Tomizawa M, Otsuka H, Miyamoto I, et al (1995) Pharmacological characteristics of insect nicotinic acethylcholine receptor with its ion channel and comparison of the effect of nicotinoids and neonicotinoids. J Pestic Sci 20:57–64
Uneme H, Higuchi N, Minamida I (1990) Preparation of chlorothiazole derivatives. Eur Pat Appl EP 446913 Al 910918
Uneme H, Higuchi N, Minamida I, Okauchi T (1988) Guanidine derivatives, their production and insecticides. Eur Pat Appl EP 376279 A2 89124012.9
Yamamoto I (1996) Neonicotinoids-mode of action and selectivity. Agrochem Jpn 68:14–15
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1999 Springer Japan
About this chapter
Cite this chapter
Maienfisch, P., Brandl, F., Kobel, W., Rindlisbacher, A., Senn, R. (1999). CGA 293’343: A Novel, Broad-Spectrum Neonicotinoid Insecticide. In: Yamamoto, I., Casida, J.E. (eds) Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor. Springer, Tokyo. https://doi.org/10.1007/978-4-431-67933-2_8
Download citation
DOI: https://doi.org/10.1007/978-4-431-67933-2_8
Publisher Name: Springer, Tokyo
Print ISBN: 978-4-431-68011-6
Online ISBN: 978-4-431-67933-2
eBook Packages: Springer Book Archive