Add time:08/19/2019         Source:sciencedirect.com

Publisher SummaryThe pyridazine nucleus is a π-deficient aromatic heterocycle. Each nitrogen atom of the 1,2-diazine activates its α- and γ-position for nucleophilic attack. Consequently, all ring carbon atoms are deactivated for electrophilic substitution. The first naturally occurring hexahydropyridazines were only reported in 1971 and the first natural product containing an aromatic pyridazine ring (Pyridazomycin) was not described before 1988. A medicinal chemistry study clearly revealed that the pyridazine ring is essential for the antimicrobial activity of this natural product since the synthesis of a deaza analog of Pyridazomycin resulted in a loss of activity. Besides the pharmaceutical applications of pyridazines there is also an agrochemical interest for these heterocycles. In 1964 BASF launched the herbicide Chloridazon. Even today Chloridazon is still used for the cultivation of sugar beet and red table beet. Norflurazon, a structurally closely related compound, was commercialized in 1971. This crop protection agent is used for the cultivation of cotton, tree fruit, and vines. Several other pyridazine herbicides were developed and some of them found the way to the market, such as Pyridate and maleic hydrazide. Besides herbicidal, there are also fungicidal pyridazines; for example, Diclomezine, which was launched in 1987 by Sankyo. Important commercial examples are the cholinesterase inhibitor Pyridaphenthion and the energy metabolism disruption agent Pyridaben.

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