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Synthesis imidacloprid

Imidacloprid has been evaluated for mutagenicity using a full complement of in vitro and in vivo tests required for registration. All tests, including the in vitro point mutation tests, in vivo chromosomal aberration tests, a mitotic recombination test in yeast, a rec assay with Bacillus subtilis, and the unscheduled DNA synthesis (UDS), were negative. [Pg.1380]

The synthesis of this compound was first described by Agro Kanesho [16]. Further preparations have been discussed in Section 29.2.3.4. As with all neonicoti-noids, AKD-1022 (12) interacts with nicotinic acetylcholine receptors however, it is much less potent than imidacloprid (8) and other commercial neonicotinoids. In particular, this has been demonstrated with Myzus and Drosophila membranes [23], as well as on American cockroaches [33]. It has been speculated that AKD-1022 (12), as a basic molecule, is ionized in the fluids of insects and, therefore, reaches the synapse only slowly through the lipophilic cuticles and the ion barriers. During retarded movement, the compound is prone to decompose, e.g., due to partial hydrolysis mediated enzymatically and/or non-enzymatically [33]. Therefore, acyclic nitroguanidines such as 19 may also contribute to the insecticidal activity observed in glasshouse and field studies. [Pg.1001]

For the synthesis of imidacloprid, three principal routes were developed. The active agent can be obtained either by modification of the basic carbon scaffold, or by building up the imidazolidine or by coupling of the two ring systems (Fig. 8.56). [Pg.744]

The first syntheses were developed in the 1980s by Kozo Shiokawa at Nihon Bayer Agrochem. The iminoimidazolidine was formed by reaction of the diamine with cyanogen bromide however, this product could be nitrated on the nitrogen in only poor yields (a). [ 145] Shigeru Kojima prepared imidacloprid by reaction of the diamine with dimethyl nitrocarboimidodithioate in dichloro-methane (b). [146] The best synthesis is probably the reaction of 2-chloro-5-(chloromethyl)pyridine and 2-nitroiminoimidazolidine with potassium carbonate in acetonitrile. [ 147] The reaction may be catalysed by 3-5 mole percent of caesium chloride (c). [148]... [Pg.745]

DKR of 1-(6[Pg.377]

In 2003, Kagabu et al. reported on the racemic synthesis of a chiral analog of imidacloprid, the reference compound of the neonicotinoid insecticide family. Although the recently synthesized Me-imidacloprid (rac-35) is less active than imidacloprid, the (5)-35 enantiomer has shown a higher potency than its (R)-counterpart. Backvall et al. developed an asymmetric synthesis leading to the active (5)-enantiomer, which includes a very efficient DKR of the alcohol intermediate rac-32 (Scheme 57.8). " ... [Pg.1688]


See other pages where Synthesis imidacloprid is mentioned: [Pg.355]    [Pg.355]    [Pg.357]    [Pg.358]    [Pg.159]    [Pg.981]    [Pg.139]    [Pg.16]   
See also in sourсe #XX -- [ Pg.983 ]




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Imidacloprid

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