Nicotine to Nicotinoids: 1962 to 1997

  • Izuru Yamamoto


Nicotine is the activ component of tobacco for smoking. It has also a long history as a medicine and an insecticide, although not competitive with modern synthetic insecticides. An excellent review on nicotine as an insecticide was presented by Schmeltz (1971). Due to its remarkable pharmacological properties, the alleged health hazard associated with tobacco smoking and nicotine use as a pesticide, its safety is constantly watched by the public. There have been enormous volumes of literature in chemistry, biochemistry, physiology, pharmacology, toxicology, entomology, botany, medicine, and psychology. However, its mode of insecticidal action was vague until Yamamoto challenged it (Yamamoto et al., 1962; Yamamoto, 1965).


Binding Affinity Insecticidal Activity AChE Inhibition Systemic Insecticide Partial Positive Charge 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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  1. Addor RW (1995) Insecticides. In: Godfrey CRA (ed) Agrochemicals from natural products. Marcel Dekker, New York, pp 10–11Google Scholar
  2. Bai D, Lummis SCR, Leicht W, Breer H, Sattelle DB (1991) Actions of imidacloprid and a related nitromethylene on cholinergic receptors of an identified insect motor neurone. Pestic Sci 33: 197–204CrossRefGoogle Scholar
  3. Beers WH, Reich E (1970) Structure and activity of acetylcholine. Nature (London) 228:917–922CrossRefGoogle Scholar
  4. Ember LR (1994) The nicotine connection. Chem Eng News Nov 28Google Scholar
  5. Fujita T, Nakajima M, Soeda Y, Yamamoto I (1971) Physicochemical properties of biological interest and structure of nicotine and its related compounds. Pestic Biochem Phvsiol 1: 151–162CrossRefGoogle Scholar
  6. Fujita T, Yamamoto I, Nakajima M (1970) Analysis of the structure-activity relationship of nicotine-like insecticides using substituent constants. In: O’Brien RD, Yamamoto I (eds) Biochemical toxicology of insecticides. Academic Press, New York, pp 21–32Google Scholar
  7. Iwata K, Takase I (1993) Admire®-a new systemic insecticide. Agrochem Jpn No. 63: 15–17Google Scholar
  8. Kamimura H, Matsumoto A, Mivazaki Y, Yamamoto I (1963) Relation of structure to toxicity ol pyridvlmethvlamines. Agric Biol Chem 27: 684–688Google Scholar
  9. Kashiwada Y (1996) Bestguard® (nitenpyram, Tl-304)-a new systemic insecticide. Agrochem Jpn, No. 68: 18–19Google Scholar
  10. Leicht W (1996) Lmidacloprid-a chloronicotinyl insecticide. Biological activity and agricultural significance. Pflanz-Nachr Bayer 49: 71–84Google Scholar
  11. Liu M-Y. Lanford J, Casida JE (1993) Relevance of [3H]imidacloprid binding site in house fly head acetylcholine receptor to insecticidal acivity of 2-nitromethylene-and 2-nitroimino-imidazolidines. Pestic Biochem Physiol 46: 200–206CrossRefGoogle Scholar
  12. Matsuda M, Takahashi H (1996) Mospilan® (acetamiprid, NI-25)-a new systemic insecticide. Agrochem Jpn, No. 68: 20–21Google Scholar
  13. Matsuo H, Tomizawa M. Yamamoto I (1998) Structure-activity relationships of acyclic nicotinoids and neonicotinoids for insect nicotinic acetylcholine receptor/ion channel complex. Arch Insect Biochem Physiol 37: 17–23CrossRefGoogle Scholar
  14. Metcalf R (1955) Organic insecticides. Interscience, New YorkGoogle Scholar
  15. Nishunura K, Kanda Y, Okazawa A. Ueno T (1994) Relationship between msecticidal and neurophysiological activities of imidacloprid and related compounds. Pestic Biochem Physiol 50: 51–59CrossRefGoogle Scholar
  16. Salgado VL (1997) The modes of action of spinosad and other insect control products. Down to Earth 52: 35–43Google Scholar
  17. Sattelle DB, Buckingham SD, Wafford KA, Sherby SM, Bakry NM, Eldefrawi AT, Eldefrawi ME, May TE (1989) Actions of the insecticide 2-(nitromethylene)-tetrahydro-l,3-thiazme on insect and vertebrate nicotinic acetylcholine receptors. Proc R Soc Lond B237: 501–514CrossRefGoogle Scholar
  18. Schmeltz I (1971) Nicotine and other tobacco alkaloids. In: Jacobson M, Crosby DG (eds) Naturally occurring insecticides. Marcel Dekker, New York, pp 99–136Google Scholar
  19. Shiokawa K, Monva K, Shibuya K, Hatlori Y, Tsuboi S, Kagabu S (1992) 3-(6-Chloronicotinyl)-2-nitromethylene-thiazolidine as a new class of insecticides acting against Lepidoptera species. Biosci Biotechnol Biochem 56:1364–1365CrossRefGoogle Scholar
  20. Shiokawa K, Tsuboi S, Kagabu S, Moriya K (1986) European Patent EP 0 192 060 AlGoogle Scholar
  21. Soeda Y, Yamamoto I (1968a) Inhibition of house fly head cholmesterase by nicotine. Agric Biol Chem 32: 568–573CrossRefGoogle Scholar
  22. Soeda Y. Yamamoto I (1968b) Relation of structure to toxicity of pyridylalkylamines. Agric Biol Chem 32: 747–752CrossRefGoogle Scholar
  23. Soloway SB, Henry AC. Kollmever WD, Padgett WM, Powell JE, Roman SA, Tieman CH. Corey RA, Home CA (1978) Nitromethylene heterocycles as insecticides. In: Shankland DL, Hollingworth RM, Smyth T (eds) Pesticide and venom neurotoxicity. Plenum, New York, pp 153–158CrossRefGoogle Scholar
  24. Tomizawa M, Matsuo IT, Miyamoto T, Yamamoto I (1996) N,N.Dialkyl substituents of 3-pyridylmethylamines discriminate between a-bungarotoxin and noncompetitive blocker sites of nicotinic acetylcholine receptors of Torpedo and insects. J. Pestic Sci 21: 412–418CrossRefGoogle Scholar
  25. Tomizawa M, Otsuka H, Miyamoto T. Yamamoto I (1995a) Phannacological effects ot imidacloprid and its related compounds on the nicotinic acetylcholine receptor with its ion channel from the Torpedo electric organ. J Pestic Sci 20: 49–56CrossRefGoogle Scholar
  26. Tomizawa M, Otsuka H, Miyamoto T, Eldefrawi M E, Yamamoto I (1995b) Phannacological characteristics of insect nicotinic acetylcholine receptor with its ion channel and the comparison of the effect of nicotinoids and neonicotionoids. J Pestic Sci 20: 57–64CrossRefGoogle Scholar
  27. Tomizawa M, Yamamoto I (1992) Binding of nicotinoids and the related compounds to the insect nicotinic acetylcholine-receptor. J Pestic Sci 17: 231–236CrossRefGoogle Scholar
  28. Tomizawa M, Yamamoto I (1993) Structure-activity relationships of nicotinoids and imidacloprid analogs. J Pestic Sci 18: 91–98CrossRefGoogle Scholar
  29. Yamamoto I (1965) Nicotinoids as insecticides. Adv Pest Control Res 6: 231–260PubMedGoogle Scholar
  30. Yamamoto I (1979) Pesticide design-insecticides. In: Yamamoto L Fiikami J (eds) Pesticide Designm: strategy and tactics. Soft Science, Tokyo, pp 891–928 (in Japanese)Google Scholar
  31. Yamamoto I (1996) Neonicotinoids-action and design. Plant Prot 50: 240–245 (in Japanese)Google Scholar
  32. Yamamoto I, Jtainimiira H, Yamamoto R. Sakai S, Goda M (1962) Studies on nicotinoids as an insecticide: relation of structure to toxicity. Agric Biol Chem 26: 709–716Google Scholar
  33. Yamamoto L Soeda Y, Kamimura II, Yamamoto R (1968) Cholinesterase. inhibition by nicotinoids and pyridylalkylammes-its significance to mode of action. Agric Biol Chem 32: 1341–1348CrossRefGoogle Scholar
  34. Yamamoto I, Tomizawa M, Saito T, Miyamoto T, Walcott EC. Sumikawa K (1998) Structural factors contributing to insecticidal and selective actions of neonicotinoids. Arch Insect Biochem Physiol 37: 24–32PubMedCrossRefGoogle Scholar
  35. Yamamoto I, Yabuta G, Tomizawa M, Saito T, Miyamoto T, Kagabu S (1995) Molecular mechanism for selective toxicity of nicotinoids and neonicotinoids. J. Pestic Sci. 20: 33–40CrossRefGoogle Scholar

Copyright information

© Springer Japan 1999

Authors and Affiliations

  • Izuru Yamamoto
    • 1
  1. 1.Department of Agricultural ChemistryTokyo University of AgricultureSetagaya-ku, TokyoJapan

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