Discovery of imidacloprid and further developments from strategic molecular designs

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 7, 2011, Pages 2887-2896

  Kagabu, Shinzo ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING MECHANISMS; CRYSTAL STRUCTURE ANALYSIS; DRUG-RECEPTOR INTERACTIONS; ELECTRON WITHDRAWING GROUP; FURTHER DEVELOPMENT; IMIDACLOPRIDS; INSECTICIDAL ACTIVITY; MOLECULAR DESIGN; NEONICOTINOID INSECTICIDES; NEONICOTINOIDS; PHARMACOPHORES; PHOTO-STABILITY; QSAR STUDIES; RATIONAL DESIGN;

COMPUTATIONAL CHEMISTRY; DRUG INTERACTIONS; INSECTICIDES; OLEFINS;

CRYSTAL STRUCTURE;

IMIDACLOPRID; IMIDAZOLE DERIVATIVE; INSECTICIDE; NITRO DERIVATIVE; PYRIDINE DERIVATIVE; THIACLOPRID; THIAZINE DERIVATIVE;

ANIMAL; APLYSIA; CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; DRUG DESIGN; DRUG STABILITY; HYDROGEN BOND; LIGHT; PERIPLANETA; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANIMALS; APLYSIA; DRUG DESIGN; DRUG STABILITY; HYDROGEN BONDING; IMIDAZOLES; INSECTICIDES; LIGHT; MODELS, MOLECULAR; NITRO COMPOUNDS; PERIPLANETA; PYRIDINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; THIAZINES;

EID: 79953902493     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf101824y     Document Type: Article

References (40)

1. Kagabu, S. Molecular design of neonicotinoids: past, present and future. In Chemistry of Crop Protection, Progress and Prospects in Science and Regulation; Voss, G., Ramos, G., Eds.; Wiley-VCH: Weinheim, Germany, 2003; pp 193-212.
2. Tomizawa, M.; Casida, J. E. Neonicotinoid insecticide toxicology: mechanism of selective action Annu. Rev. Pharmacol. Toxicol. 2005, 45, 247-268 (Pubitemid 40261805)
3. Matsuda, K.; Shimomura, M.; Ihara, M.; Akamatsu, M.; Sattelle, D. B. Neonicotinoids show selective and diverse actions on their nicotinic receptor targets: electrophysiology, molecular biology, and receptor modeling studies Biosci., Biotechnol., Biochem. 2005, 69, 1442-1452 (Pubitemid 41207331)
4. Jeschke, P.; Nauen, R. Neonicotinoids-from zero to hero in insecticide chemistry Pest Manag. Sci. 2008, 64, 1084-1098
5. Kagabu, S. Chloronicotinyl insecticides-discovery, application, and future perspective Rev. Toxicol. 1997, 1, 75-129 (Pubitemid 127735347)
6. Kagabu, S. Discovery of chloronicotinyl insecticides. In Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor; Yamamoto, I.; Casida, J. E., Eds.; Springer: Berlin, Germany, 1999; pp 91-106.
7. Kollmeyer, W. D.; Flattum, R. F.; Foster, R. F.; Powell, J. E.; Schroeder, M. E.; Soloway, S. B. Discovery of the nitromethylene heterocycle insecticides. In Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor; Yamamoto, I.; Casida, J. E., Eds.; Springer: Berlin, Germany, 1999; pp 71-89.
8. Diehr, H.-J.; Gallenkamp, B.; Jelich, K.; Lantzsch, R.; Shiokawa, K. Synthesis and chemical-physical properties of the insecticide imidacloprid (NTN 33893) Pflanzenschutz-Nachr. Bayer 1991, 44, 107-112
9. Jeschke, P.; Moriya, K.; Lantzsch, R.; Seifert, H.; Lindner, W.; Jelich, K.; Gohoert, A.; Beck, M. E.; Etzel, W. Thiacloprid (Bay YRC 2894)-a new member of the chloronicotinyl insecticide (CNI) family Pflanzenschutz-Nachr. Bayer 2001, 54, 147-160
10. Kagabu, S.; Medej, S. Chloronicotinyl insecticides-stability comparison of imidacloprid and related compounds under simulated sunlight, hydrolysis conditions, and to oxygen Biosci., Biotechnol., Biochem. 1995, 59, 980-985
11. Kagabu, S.; Akagi, T. Quantum chemical considerations of photostability of imidacloprid and related compounds J. Pestic. Sci. 1997, 21, 231-239
12. Iwaya, K.; Tsuboi, S. Imidacloprid-a new substance for the control of rice pests in Japan Pflanzenschutz-Nachr. Bayer 1992, 45, 197-230
13. Akayama, A.; Minamida, I. Discovery of a new systemic insecticide, nitenpyram and its insecticidal properties. In Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor; Yamamoto, I.; Casida, J. E., Eds.; Springer: Berlin, Germany, 1999; pp 127-148.
14. Yamada, T.; Takahashi, H.; Hatano, R. A novel insecticide, acetamiprid. In Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor; Yamamoto, I.; Casida, J. E., Eds.; Springer: Berlin, Germany, 1999; pp 149-176.
15. Wakita, T.; Kinoshita, K.; Yamada, E.; Yasui, N.; Kawahara, N.; Naoi, A.; Nakaya, M.; Ebihara, K.; Matsuno, H.; Kodaka, K. The discovery of dinotefuran: a noval neonicotinoid. Pest Manage. Sci. 2003, 59, 1016-1022.
16. TM) family. Pflanzenschutz-Nachr. Bayer 2003, 56, 5-25.
17. Maienfisch, P.; Brandl, F.; Kobel, W.; Rindisbacher, A.; Senn, R. CGA 293343: a novel broad-spectrum neonicotinoid insecticide. In Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor; Yamamoto, I.; Casida, J. E., Eds.; Springer: Berlin, Germany, 1999; pp 177-209.
18. Wu, F.; Kariya, A.; Katsuyama, N.; Tsuji, A.; Takasuka, K.; Segami, S.; Nanjo, K.; Sato, J. (Agro-Kanesho Co., Ltd.) Preparation of hexahydrotriazine compounds as insecticides. Eur. Pat. Appl. EP 428941 A1 19910529, 1991.
19. Kagabu, S.; Matsuno, H. Chloronicotinyl insecticides. 8. Crystal and molecular structures of imidacloprid and analogous compounds J. Agric. Food Chem. 1997, 45, 276-281 (Pubitemid 127485791)
20. 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
21. Kagabu, S.; Ishihara, R.; Hieda, Y.; Nishimura, K.; Naruse, Y. Insecticidal and neuroblocking potencies of variants of the imidazolidine moiety of imidacloprid-related neonicotinoids and the relationship to partition coefficient and charge density on the pharmacophore J. Agric. Food Chem. 2007, 55, 812-818
22. Kagabu, S.; Nishimura, K.; Naruse, Y.; Ohno, I. Insecticidal and neuroblocking potencies of variants of the thiazolidine moiety of thiacloprid and quantitative relationship study for the key neonicotinoid pharmacophore J. Pestic. Sci. 2008, 33, 58-66 (Pubitemid 351329102)
23. Okazawa, A.; Akamatsu, M.; Ohoka, A.; Nishiwaki, H.; Cho, W. J.; Nakagawa, Y.; Nishimura, K.; Ueno, T. Prediction of the binding mode of imidacloprid and related compounds to house fly head acetylcholine receptors using three-dimensional QSAR analysis Pestic. Sci. 1998, 54, 134-144 (Pubitemid 28490183)
24. Kagabu, S.; Ito, N.; Imai, R.; Hieda, Y.; Nishimura, K. Effects of halogen introduction at the C5 position of the imidacloprid pyridine ring upon insecticidal activity J. Pestic. Sci. 2005, 30, 111-115
25. Nishimura, K.; Kiriyama, K.; Kagabu, S. Quantitative structure-activity relationships of imidacloprid and its analogues with substituents at the 5th position on the pyridine ring in the neuroblocking activity J. Pestic. Sci. 2006, 31, 110-115 (Pubitemid 43800292)
26. Kagabu, S.; Fujii, Y.; Nishimura, K. Insecticidal activity of imidacloprid derivatives with an alkoxy group at the 5th position of the pyridine ring J. Pestic. Sci. 2006, 31, 150-155 (Pubitemid 43800298)
27. Kagabu, S.; Hieda, Y.; Ohno, I. Preparation of 5-chloror-6- fluoronicotinyl insecticides and comparison of their insecticidal activity in a laboratory test with 6-chloro-5-fluoro analog J. Pestic. Sci. 2007, 32, 260-263 (Pubitemid 47347654)
28. Kagabu, S.; Maienfisch, P.; Zhang, A.; Granda-Minones, J.; Haettenschweiler, J.; Kaiser, H.; Casida, J. E. 5-Azidoimidacloprid and an acyclic analogue as candidate photoaffinity probes for mammalian and insect nicotinic acetylcholine receptors J. Med. Chem. 2000, 43, 5003-5009 (Pubitemid 32039021)
29. Zhang, N.; Tomizawa, M.; Casida, J. E. Structural features of azidopyridinyl neonicotinoids probes conferring high affinity and selectivity for mammalian α4β2 and Drosophila nicotinic acetylcholine receptors J. Med. Chem. 2002, 45, 2832-2840 (Pubitemid 34627653)
30. Tomizawa, M.; Casida, J. E. Molecular recognition of neonicotinoid insecticides: the determinants of life or death Acc. Chem. Res. 2009, 42, 26-269
31. Nishimura, K.; Tanaka, M.; Iwaya, K.; Kagabu, S. Relationship between insecticidal and nerve-excitatory activities of imidacloprid and its alkylated congeners at the imidazolidine NH site Pestic. Biochem. Physiol. 1998, 62, 172-178 (Pubitemid 29092133)
32. Nishiwaki, H.; Nakagawa, Y.; Ueno, T.; Kagabu, S.; Nishimura, K. Pest. Manag. Sci. 2001, 57, 810-814.
33. 3H] imidacloprid-binding sites on nicotinic acetylcholine receptor J. Pestic. Sci. 2002, 27, 249-256 (Pubitemid 35343552)
34. Kagabu, S.; Itazu, Y.; Nishimura, K. Preparation of alkylene-tethered acyclic divalent neonicotinoids and their insecticidal and neuroblocking activities for American cockroach (Periplaneta americana L.). J. Pestic. Sci. 2004, 29, 40-42. (Pubitemid 41150808)
35. Ihara, M.; Hirata, K.; Ishida, C.; Kagabu, S.; Matsuda, K. Blocking actions of alkylene-tethered bis-neonicotinoids on nicotinic acetylcholine receptors expressed by terminal abdominal ganglion neurons of Periplaneta americana Neurosci. Lett. 2007, 425, 137-140 (Pubitemid 47418357)
36. Ohno, I.; Tomizawa, M.; Durkin, K. A.; Casida, J. E.; Kagabu, S. Bis-neonicotinoid insecticides: observed and predicted binding interactions with the nicotinic receptor Bioorg. Med. Chem. Lett. 2009, 19, 3449-3452
37. Mori, M.; Kikuchi, M.; Ohno, I.; Kagabu, S. Unexpected plant-systemic insecticidal properties of alkylene-tethered bis-imidacloprid derivatives. J. Pestic. Sci. 2010, 35, 124-130.
38. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches of to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 1997, 23, 3-25 (Pubitemid 27046991)
39. Tice, C. M. Selecting the right compounds for screening: does Lipinski's rule of 5 for pharmaceuticals apply to agrochemicals? Pest Manag. Sci. 2001, 57, 3-16 (Pubitemid 32095657)
40. Moriguchi, I.; Hirono, S.; Liu, Q; Nakagome, I.; Matsushita, Y. Simple method of calculating octanol/water partition coefficient Chem. Pharm. Bull. 1992, 40, 127-130