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Synthesis and Biological Evaluation of Thymol Functionalized Oxadiazole thiol, Triazole thione and β-lactam Derivatives
Letters in Organic Chemistry ( IF 0.8 ) Pub Date : 2021-05-31 , DOI: 10.2174/1570178617999200807213410
Jyoti Gaba 1 , Sunita Sharma 2 , Pardeep Kaur 1 , Sukesha Joshi 1
Affiliation  

In the present study, different derivatives of thymol (1) viz. hydrazide (2), oxadiazole thiol (3), triazole thione (4), hydrazones (5-7), and β-lactams (8-10) were synthesized. All synthesized compounds were identified and characterized using elemental analysis, UV-Visible, 1H NMR, 13C NMR, and IR spectroscopic techniques. Synthesized thymol derivatives were evaluated for antifungal potential against phytopathogenic fungi Fusarium moniliforme, Rhizoctonia solani, and Dreschlera maydis of maize in comparison to recommended standards in terms of percent inhibition and ED50 values. Thymol was more effective as compared to its derivatives against all three tested fungi. Hydrazones (5-7) and β-lactams (8-10), having m-NO2 substituted phenyl ring (6, 9), were less effective as compared to o-NO2 and p-NO2 analogs against F. moniliforme and R. solani, however, the reverse trend was observed against D. maydis. Thymol and its derivatives were also tested for insecticidal activity against stored grain (chickpea) insect Callosobruchus chinensis and various parameters viz. egg laying, adult emergence, and grain damage were recorded and compared. Compounds having oxadiazole thiol (3) and triazole thione (4) moiety showed promising effects against insect C. chinensis.



中文翻译:

百里酚官能化恶二唑硫醇、三唑硫酮和 β-内酰胺衍生物的合成和生物学评价

在本研究中,百里酚 (1) 的不同衍生物即。合成了酰肼 (2)、恶二唑硫醇 (3)、三唑硫酮 (4)、腙 (5-7) 和 β-内酰胺 (8-10)。所有合成的化合物都使用元素分析、紫外-可见光、1 H NMR、13 C NMR 和红外光谱技术进行鉴定和表征。在抑制百分比和 ED50 值方面,与推荐的标准相比,评估了合成的百里酚衍生物对玉米的植物病原真菌念珠菌镰刀菌、立枯丝核菌和玉米螟病的抗真菌潜力。与它的衍生物相比,百里酚对所有三种测试真菌更有效。腙 (5-7) 和 β-内酰胺 (8-10),具有 m-NO 2取代的苯环 (6, 9) 与 o-NO 2和 p-NO 2类似物相比,对念珠菌和茄属植物的效果较差,但是,观察到对玉米假单胞菌的相反趋势。还测试了百里酚及其衍生物对贮粮(鹰嘴豆)昆虫 Callosobruchus chinensis 的杀虫活性和各种参数,即。记录和比较产卵、成虫羽化和谷物损伤。具有恶二唑硫醇 (3) 和三唑硫酮 (4) 部分的化合物对昆虫 C. chinensis 显示出有希望的效果。

更新日期:2021-06-04
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