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A new method for the synthesis and herbicidal activity of 3-phenoxy-6-(1H-(substituted)pyrazol-1-yl) pyridazines

✍ Scribed by Fang-Zhong Hu; Gui-Feng Zhang; Bin Liu; Xiao-Mao Zou; You-Quan Zhu; Hua-Zheng Yang

Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
189 KB
Volume
46
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A series of 3‐substituted phenoxy‐6‐((substituted)1H‐pyrazol‐1‐yl) pyridazines were synthesized from the condensation of various phenols and 3‐chloro‐6‐(1H‐pyrazol‐1‐yl) pyridazine 2 or 3‐chloro‐6‐(5′‐methyl‐4‐ethoxycarbonyl‐1H‐pyrazol‐1‐yl) pyridazine 6 in N,N‐dimethylformamide (DMF) at 120°C with K~2~CO~3~ as an acid receptor. The intermediates 2 or 6 were obtained from the cyclization of 3‐chloro‐6‐hydrazinyl pyridazine 1 with 3‐dimethylamino‐acrylaldehyde or ethyl 2‐((dimethylamino) methylene)‐3‐oxobutanoate in n‐butanol under reflux, respectively, and side products 3 or 7 were also generated. All of the title compounds were confirmed by ^1^H NMR, infrared spectometry (IR) and elemental analyses. Preliminary bioassay indicated that some of the title compounds showed high inhibitory activity against Brassica campestris L. (B. campestris) and moderate inhibitory activity against Echinochloa crusgalli. For example, the inhibition percentages of compound 4b and 4c against B. campestris were both 94% at 10 μg/mL. J. Heterocyclic Chem., (2009).

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