Chloronicotinyl Insecticides. 8. Crystal and Molecular Structures of Imidacloprid and Analogous Compounds

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 1, 1997, Pages 276-281

  Kagabu, Shinzo ^a   Matsuno, Hirozumi ^b  

^a GIFU UNIVERSITY   (Japan)

^b MITSUI CHEMICALS INC   (Japan)

Author keywords

Chloronicotinyl insecticide; Imidacloprid; Nicotinic acetylcholine receptor; Nitromethylene insecticide; X ray structure

Indexed keywords

EID: 0000602517     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf960075f     Document Type: Article

References (30)

1. Bai, D.; Lummis, R. C. S.; Leicht, W.; Breer, H.; Sattelle, B. D. Actions of imidacloprid and a related nitromethylene on cholinergic receptors of an identified insect motor neurone. Pestic. Sci. 1991, 33, 197-204.
2. Beers, W. H.; Reich, E. Structure and activity of acetylcholine. Nature 1970, 228, 917-922.
3. Breer, H.; Sattelle, D. B. Molecular properties and functions of insect acetylcholine receptors. J. Insect Physiol. 1987, 33, 771-790.
4. Camilleri, P.; Carey, J. V.; Odell, B.; Williams, D. J. J. Chem. Soc., Perkin Trans. 2 1988, 591-596.
5. 125I]-α-bungarotoxin. J. Neurosci. 1985, 5, 1307-1315.
6. Galzi, J.-L.; Revah, F.; Bessis, A.; Changeux, J.-P. Functional architecture of the nicotinic acetylcholine receptor. Annu. Rev. Pharmacol. 1991, 31, 37-72.
7. Herz, J. M.; Johnson, D. A.; Taylor, P. Distance between the agonist and noncompetitive inhibitor sites on the nicotinic acetylcholine receptor. J. Biol. Chem. 1989, 25, 12439-12448.
8. Ishii, Y.; Kobori, I.; Araki, Y.; Kurogochi, S.; Iwaya, K.; Kagabu, S. HPLC determination of the new insecticide imidacloprid and its behavior in rice and cucumber. J. Agric. Food Chem. 1994, 42, 2917-2921.
9. Kagabu, S. New insecticide imidacloprid (in Japanese). Chem. Biol. 1993, 31, 521-523.
10. Kagabu, S. Study on the synthesis and insecticidal activity of neonicotinoid compounds. J. Pestic. Sci. 1996, 21, 231-239.
11. Kagabu, S.; Medej, S. Stability comparison of imidacloprid and related compounds under simulated sunlight, hydrolysis conditions, and to oxygen. Biosci., Biotechnol., Biochem. 1995, 59, 980-985.
12. Kagabu, S.; Moriya, K.; Shibuya, K.; Hattori, Y.; Tsuboi, S.; Shiokawa, K. 1-(6-Halonicotinyl)-2-nitromethylene-imidazolidines as potential new insecticides. Biosci., Biotechnol., Biochem. 1992, 56, 361-363.
13. Leicht, W.; Imidacloprid - a chloronicotinyl insecticide. Pestic. Outlook 1993, 4, 17-21.
14. 3H]-imidacloprid in the insect acetylcholine receptor. Pestic. Biochem. Physiol. 1993, 46, 40-46.
15. Moffat, S. New chemicals seek to outwit insect pests. Science 1993, 261, 550-551.
16. Moriya, K.; Shibuya, K.; Hattori, Y.; Tsuboi, S.; Shiokawa, K.; Kagabu, S. 1-(6-Chloronicotinyl)-2-nitroimino-imidazolidines and related compounds as potential new insecticides. Biosci., Biotechnol., Biochem. 1992, 56, 364-365.
17. Moriya, K.; Shibuya, K.; Hattori, Y.; Tsuboi, S.; Shiokawa, K.; Kagabu, S. Structural modification of the 6-chloropyridyl moiety in the imidacloprid skeleton: introduction of a five-membered heteroaromatic ring and the resulting insecticidal activity. Biosci., Biotechnol. Biochem. 1993a, 57, 127-128.
18. Moriya, K.; Shibuya, K.; Hattori, Y.; Tsuboi, S.; Shiokawa, K.; Kagabu, S. 1-Diazinylmethyl-2-nitromethylene- and 2-nitroimino-imidazolidines as new potential insecticides. J. Pestic. Sci. 1993b, 18, 119-123.
19. Nishimura, K.; Kanda, Y.; Okazawa, A.; Ueno, T. Relationships between insecticidal and neurophysiological activities of imidacloprid and related compounds. Pestic. Biochem. Physiol. 1994, 50, 51-59.
20. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH Verlag.: Weinheim, 1988; Chapter 4.
21. Sasada, Y. Molecular and crystal structures. In Chemistry Handbook (in Japanese), 3rd ed.; The Chemical Society of Japan, Maruzen: Tokyo, 1984; Chapter 15.
22. Sattelle, D. B.; Buckingham, S. D.; Wafford, K. A.; Sherby, S. M.; Bakry, N. M.; Elderfrawi, R. T.; Elderfrawi, M. E.; May, T. E. Action of the insecticide 2-(nitromethylene)tetrahydro-1,3-thiazine on insect and vertebrate nicotinic acetylcholine receptors. Proc. R. Soc. London 1989, B237, 501-514.
23. Schofield, K. Heteroaromatic Nitrogen Compounds; Butterworth: London, 1967; Chapter 5.
24. Schroeder, M. E.; Flattum, R. F. The mode of action and neurotoxic properties of the nitromethylene heterocycle insecticides. Pestic. Biochem. Physiol. 1984, 22, 148-160.
25. Shiokawa, K.; Moriya, K.; Shibuya, K.; Hattori, Y.; Tsuboi, S.; Kagabu, S. 3-(6-Chloronicotinyl)-2-nitromethylene-thiazo-lidine as a new class of insecticide acting against Lepidoptera species. Biosci. Biotech. Biochem., 1992, 56, 1364-1365.
26. Taft, R. W. Separation of polar, steric, and resonance effects in reactivity. In Steric Effects in Organic Chemistry; Newman, M. S., Ed.; Wiley: New York, 1956; Chapter 13.
27. Tomizawa, M.; Yamamoto, I. Structure-activity relationships of nicotinoids and imidacloprid analogs. J. Pestic. Sci. 1993, 18, 91-98.
28. Vinogradov, S. N.; Linnell, R. H. Hydrogen Bonding; Van Nostrand Reinhold: New York, 1971; Chapter 6.
29. Yamamoto, I.; Tomizawa, M. New development of nicotinoid insecticides. In Pesticides/Environment: Molecular Biological Approaches; Mitsui, T., Matsumura, F., Yamaguchi, I., Eds.; Pesticide Science Society of Japan: Tokyo, 1993; pp 67-85.
30. Yamamoto, I.; Yabuta, G.; Tomizawa, M.; Saito, T.; Miyamoto, T.; Kagabu, S. Molecular mechanism for selective toxicity of nicotinoids and neonicotinoids. J. Pestic. Sci. 1995, 20, 33-40.