Design, synthesis, and characterization of 2,2-bis(2,4-dinitrophenyl)-2-(phosphonatomethylamino)acetate as a herbicidal and biological active agent.

Journal of Chemical Biology Pub Date : 2017-07-09 eCollection Date: 2017-10-01 DOI:10.1007/s12154-017-0174-z
Vijay Kumar, Simranjeet Singh, Rohit Singh, Niraj Upadhyay, Joginder Singh
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引用次数: 39

Abstract

The present study was designed to synthesize the bioactive molecule 2,2-bis(2,4-dinitrophenyl)-2-(phosphonatomethylamino)acetate (1), having excellent applications in the field of plant protection as a herbicide. Structure of newly synthesized molecule 1 was confirmed by using the elemental analysis, mass spectrometric, NMR, UV-visible, and FTIR spectroscopic techniques. To obtain better structural insights of molecule 1, 3D molecular modeling was performed using the GAMESS programme. Microbial activities of 1 were checked against the pathogenic strains Aspergillus fumigatus (NCIM 902) and Salmonella typhimurium (NCIM 2501). Molecule 1 has shown excellent activities against fungal strain A. fumigates (35 μg/l) and bacterial strain S. typhimurium (25 μg/l). To check the medicinal significance of molecule 1, interactions with bovine serum albumin (BSA) protein were checked. The calculated value of binding constant of molecule 1-BSA complex was 1.4 × 106 M-1, which were similar to most effective drugs like salicylic acid. More significantly, as compared to herbicide glyphosate, molecule 1 has exhibited excellent herbicidal activities, in pre- and post-experiments on three weeds; barnyard grass (Echinochloa Crus), red spranglitop (Leptochloa filiformis), and yellow nuts (Cyperus Esculenfus). Further, effects of molecule 1 on plant growth-promoting rhizobacterial (PGPR) strains were checked. More interestingly, as compared to glyphosate, molecule 1 has shown least adverse effects on soil PGPR strains including the Rhizobium leguminosarum (NCIM 2749), Pseudomonas fluorescens (NCIM 5096), and Pseudomonas putida (NCIM 2847).

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2,2-双(2,4-二硝基苯基)-2-(膦甲基胺)醋酸酯除草和生物活性剂的设计、合成和表征。
本研究旨在合成具有生物活性的分子2,2-二(2,4-二硝基苯基)-2-(磷原子乙基氨基)乙酸酯(1),作为除草剂在植物保护领域有很好的应用。通过元素分析、质谱、核磁共振、紫外可见和红外光谱等技术对新合成分子1的结构进行了确证。为了更好地了解分子1的结构,使用GAMESS程序进行了三维分子建模。对病原菌烟曲霉(NCIM 902)和鼠伤寒沙门菌(NCIM 2501)进行微生物活性测定。分子1对烟熏A. (35 μg/l)和鼠伤寒S. (25 μg/l)具有较好的抑制活性。为了检验分子1与牛血清白蛋白(BSA)蛋白相互作用的药理意义。分子1-BSA复合物的结合常数计算值为1.4 × 106 M-1,与水杨酸等大多数有效药物的结合常数相近。更显著的是,与除草剂草甘膦相比,分子1在三种杂草的实验前和实验后均表现出优异的除草活性;谷仓草(Echinochloa Crus),红色的柳叶(Leptochloa filformis)和黄色的坚果(Cyperus Esculenfus)。进一步研究了分子1对植物促生根瘤菌(PGPR)菌株的影响。更有趣的是,与草甘膦相比,分子1对豆类根瘤菌(NCIM 2749)、荧光假单胞菌(NCIM 5096)和恶臭假单胞菌(NCIM 2847)等土壤PGPR菌株的不良影响最小。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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