Five-membered Compounds - Imidacloprid and Thiacloprid

Koyanagi, T. Haga, Bioisosterism in agrochemicals. In Synthesis and Chemistry of Agrochemicals IV. Baker R., Fenyes J. G., Basarab G. S. (eds). American Chemical Society, Washington D.C., 1995, Chapter 2, pp. 15-24. 

Kagabu, in Chemistry of Crop Protection Progress and Prospects in 

Okazawa, M. Akamatsu, H. Nishiwaki, Y. Nakagawa, H. Miyagawa, K. Nishimura, T. Ueno, Pest Manag. Sci. 2000, 56, 509-515. 

Jeschke, R. Nauen in Comprehensive Molecular Insect Science (Eds. 

Two commercial neonicotinoids containing five-membered ring systems belong to this group, imidacloprid (1) and thiadoprid (9). 

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Five-membered Compounds - Imidacloprid and Thiacloprid 983 Table 29.2.2.2 Physicochemical properties of imidacloprid (1). 

From the lead structure 2-nitromethylene-tetrahydro-l,3-thiazine (6, nithiazine) [7, 8], resulting neonicotinoids [9] such as the open-chain compounds, e.g., nitenpyram (8), acetamiprid (9), dothianidin (12), dinotefuran (13) (Chapter 29.2.1), the five-membered ring systems, e.g., imidacloprid (7), thiacloprid (11) (Chapter 29.2.2), and the six-membered ring systems, e.g., thiamethoxam (10), AKD 1022 (14)... 

The N-cyano-acetamidine acetamiprid (2, 1995, Nippon Soda Co., Ltd.) [16, 17, 18] contains, in analogy to 1 and the five-membered ring systems imidacloprid (11) and thiacloprid (12), the CPM moiety (see Chapter 29.2.2). It was discovered by Nippon Soda as part of its nitromethylene research program during optimization studies of special 2-N-cyanoimino compounds with an imidazoline... 

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