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首页> 外文期刊>Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry >Synthesis and herbicidal activity of novel 4-acyl-2,5-disubstituted-3- hydroxypyrazoles and 4-arylcarbonyl-3-substitutedisoxazol-5-ones
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Synthesis and herbicidal activity of novel 4-acyl-2,5-disubstituted-3- hydroxypyrazoles and 4-arylcarbonyl-3-substitutedisoxazol-5-ones

机译：新型4-酰基-2,5-二取代-3-羟基吡唑和4-芳基羰基-3-取代异恶唑-5-酮的合成及除草活性

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摘要

Two series of novel 4-acyl-2,5-disubstituted-3-hydroxypyrazoles 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h and 4-arylcarbonyl-3-substitutedisoxazol-5-ones 7a, 7b, 7c, 7d, 7e, 7f, 7g, 7h, 7i were synthesized by the Scotton-Baumann reaction of 2,5-disubstituted-2,4-dihydro-pyrazol-3-ones 1 or 3-substituted-4H-isoxazol-5- ones 6 and various acyl chlorides, followed by the Fries rearrangement in the presence of calcium hydroxide and calcium oxide as the catalyst. Their structures were confirmed by IR, ~1H NMR, mass spectroscopy, and elemental analyses. ~1H NMR indicated that compounds 3 existed in enol forms and compounds 7 in keto configurations. The results of preliminary bioassays showed that some of the title compounds 3 and 7 exhibited moderate to good herbicidal activities against Brassica campestris L. at the concentration of 100 mg/L. Isoxazole compounds 7 showed better herbicidal activity against B. campestris L. than pyrazole compounds 3 did at the concentration of 100 mg/L. Moreover, most of the isoxazole compounds displayed higher herbicidal activity against B. campestris L. than Echinochloa crus-galli. However, these compounds showed weak herbicidal activities at the concentration of 10 mg/L.
机译：两个系列的新颖的4-酰基-2,5-二取代-3-羟基吡唑3a，3b，3c，3d，3e，3f，3g，3h和4-芳基羰基-3-取代的异恶唑-5-酮7a，7b，7c，通过2,5-二取代-2,4-二氢-吡唑-3-酮1或3-取代的-4H-异恶唑-5-酮的Scotton-Baumann反应合成7d，7e，7f，7g，7h，7i 6和各种酰基氯，然后在氢氧化钙和氧化钙作为催化剂的情况下进行弗里斯重排。通过IR，〜1H NMR，质谱和元素分析确认了它们的结构。 〜1 H NMR表明化合物3以烯醇形式存在且化合物7以酮构型存在。初步生物测定的结果表明，某些标题化合物3和7在100 mg / L的浓度下对菜子油菜表现出中等至良好的除草活性。异恶唑化合物7在100 mg / L的浓度下比吡唑化合物3具有更好的除草活性。此外，大多数异恶唑化合物对野菜双歧杆菌的除草活性均高于棘孢gal藜。但是，这些化合物在10 mg / L的浓度下除草活性较弱。

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