S. Tamura, T. Jojima
Sep 1, 1963
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Agricultural and biological chemistry
Abstract
Physiological activity of substituted pyridazines has not been studied so extensively, as compared with those of pyridine, pyrimidine and s-triazine derivatives. Recently some interests have grown in this field and various pyridazine derivatives were synthesized for the examination of structure-activity relations by several workers. Fischer 1) tested herbicidal property of pyridazone derivatives and showed that 5-amino-4-chloro-1, 2-dihydro-6-oxo-l-phenyl-pyridazone (I) has the best activity. With relation to the effectiveness of (2, 4-dichlorophenoxy) acetic acid as the herbicide, syntheses of (3-chloro-pyridaz-6-oxy) acetic acid (II) and related compounds have been disclosed in a German patent 2). Steck et al. 3, 4) prepared a few 3-chloro-6-phenoxypyridazines substituted at their benzene rings, besides 3chloro-6-alkoxyand 3, 6-dialkoxy-pyridazines, for eventual pharmaceutical trials. Few attempts have been made, however, for the systematic evaluation of physiological activities of pyridazyl phenyl ethers, especially for the evaluation as herbicides. These situations led the authors to the serial synthesis of 3chloro-6-phenoxypyridazines (III) and 3, 6-bisphenoxypyridazines (IV) to find new herbicides among these compounds. Pyridazyl