Methyl, trifluoromethyl, and methoxycarbonyl - Introduction to the fifth position on the pyridine ring of chloronicotinyl insecticide imidacloprid

Synthetic Communications

Volumn 36, Issue 9, 2006, Pages 1235-1245

  Kagabu, Shinzo ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

Chloronicotinyl insecticide; Imidacloprid; Neonicotinoid; Prodrug; Substituted pyridine

Indexed keywords

CARBONYL DERIVATIVE; CHLORINE DERIVATIVE; IMIDACLOPRID; INSECTICIDE; METHYL GROUP; PYRIDINE;

ARTICLE; CHEMICAL REACTION KINETICS; DECOMPOSITION; ELECTRON TRANSPORT; HYDROPHILICITY; SYNTHESIS;

EID: 33645320838     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500516134     Document Type: Article

References (16)

1. Kagabu, S. Chloronicotinyl insecticides - discovery, application and future perspective. Rev. Toxicol. 1997, 1, 75-129.
2. Yamamoto, I.; Casida, J. E. Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor. Springer: Tokyo, 1999; p. 300.
3. Nauen, R.; Ebbighaus-Kinscher, U.; Elbert, A.; Jeschke, P.; Tietjen, K. Acetylcholine receptors as sites for developing neonicotinoid insecticides. In Biochemical Sites of Insecticide Action and Resistance; Ishaaya, I., Ed.; Springer: Berlin, 2001; pp. 77-105.
4. 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: Weiheim, 2003; pp. 193-212.
5. Nishiwaki, H.; Nakagawa, Y.; Takeda, D.; Okazawa, A.; Akamatsu, M.; Miyagawa, H.; Ueno, T.; Nishimura, K. Binding activity of substituted benzyl derivatives of chloronicotinyl insecticides to housefly-head membranes and its relationship to insecticidal activity against the housefly Musca domestica. Pest Manag. Sci. 2000, 56, 875-881.
6. Gsell, L. Preparation and testing of [(pyridylmethyl)amino]- nitroethylenes as insecticides, acaricides and ectoparasitcides. Eur. Pat. Appl. EP 302833 A2 19890208, 1989; Chem. Abst. 1989, 111, 39194.
7. Gsell, L. Preparation and testing of pyridylmethylcyanoguanidines as insecticides and acaricides. Eur. Pat. Appl. EP 306696 A1 19890315, 1989; Chem. Abst. 1989, 111, 97093.
8. Kagabu, S.; Ogawa, M.; Makimura, M.; Nishimura, K. Insecticidal and neuroblocking activities in the American cockroach (Periplaneta americana L.) of Mannich bases of nitromethylene imidazolidine neonicotinoids. J. Pestic. Sci. 2005, 30, 44-46.
9. Drabek, J.; Neuman, R. Proinsecticides. In Progress in Pesticide Biochemistry and Toxicology; Huston, D. H., Roberts, T. R., Eds.; Wiley: New York, 1985; pp. 35-86.
10. Hawkins, F. G.; Roe, A. Preparation of 5-fluoronicotinic acid and 5-fluoronicotinamide. J. Org. Chem. 1949, 14, 328-332.
11. Setliff, F. L.; Rankin, G. O. Some 2,5- and 5,6-dihalonicotinic acids and their precursors. II. J. Chem. Eng. Data 1972, 17, 515-516.
12. Setliff, F. L.; Lane, J. E. Some 2,5- and 5,6-dihalonicotinic acids and their precursors. IV. J. Chem. Eng. Data 1976, 21, 246-247.
13. Dunn, A. D. Nucleophilic displacement in 2-chloro(trifluoromethyl) pyridines with amines and ammonia. J. Fluorine Chem. 1999, 93, 153-157.
14. Tschaen, D. M.; Desmound, R.; King, A. O.; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. An improved procedure for aromatic cyanation. Synth. Commun. 1994, 24, 887-890.
15. Morisawa, Y.; Kataoka, M.; Sakamoto, T.; Nagohori, H.; Kitano, N.; Kusano, K. Studies on anticoccidial agents; 12, Synthesis and anticoccidial activity of methyl-2(6)-nitro- and 3(5)-nitropyridinecarboxamides. J. Med. Chem. 1978, 21, 194-199.
16. Sreevasulu, M.; Rao, K. A one-pot synthesis of 2-chloronicotinonitriles and fused 2-chloro-3-cyanopyridines. Indian J. Chem. 1989, 28B, 584-586.