Unexpected formation of N'-phenyl-thiophosphorohydrazidic acid O,S-dimethyl ester from acephate: chemical, biotechnical and computational study.
Unexpected formation of N'-phenyl-thiophosphorohydrazidic acid O,S-dimethyl ester from acephate: chemical, biotechnical and computational study.
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DOI：
10.1007/s13205-015-0313-6
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发表时间：
2016-06
期刊：
影响因子：
2.8
通讯作者：
Upadhyay N
中科院分区：
文献类型：
--
作者：
Kumar V;Kaur S;Singh S;Upadhyay N
在水介质中，苯肼与乙酰甲胺磷发生亲核反应，得到稳定的产物N‘-苯基-硫代磷酰肼-O，S-二甲酯(1)，经元素分析、光谱分析和热分析表征。根据Coats-Redfern方程，热力学参数Ea、ΔH°、ΔS°和ΔG°分别为62.15、−67.95、−0.068和−20.05kJ·−_1。用紫外-可见光谱和傅里叶变换红外光谱分析了1与BSA蛋白的相互作用。观察到的结合常数为1.12(±0.0 9)×10~4×10~4−-1。考察了1对豆类根瘤菌、荧光假单胞菌、柠檬节杆菌、短杆菌和鼠伤寒沙门氏菌等植物生长促进剂的生物学效应，并与亲本分子乙酰甲胺磷进行了比较，发现1对植物生长促进剂的毒性低于乙酰甲胺磷。红外光谱几何参数和峰位值的实验结果与GAMESS软件的计算结果吻合较好。从理论上合成了12个新的类似物，并讨论了它们的比较反应性(HOMO-LUMO能)和生物分解(基于极化率)。本文的在线版本(doi：10.1007/s13205-0150313-6)包含补充材料，授权用户可以使用。
By the nucleophilic attack of phenylhydrazine on acephate in aqueous medium, a stable product N′-phenyl-thiophosphorohydrazidic acid O,S-dimethyl ester (1) was obtained and characterized by elemental, spectral and thermal analysis. Thermodynamic parameters, Ea, ΔH°, ΔS° and ΔG°, have found to be 62.15, −67.95, −0.068 and −20.05 kJ mol−1 according to the Coats–Redfern equation. Analysis of interaction of 1 with BSA protein was done by using the UV–Vis and FTIR spectroscopic methods. The observed binding constants was 1.12 (±0.09) × 104 M−1. The biological effect of 1 was checked on different plant growth-promoting (PGPR) strains such as Rhizobium leguminosarum, Pseudomonas fluorescens, Arthrobacter citreus, Bacillus brevis and Salmonella typhimurium and compared with parent molecule acephate where 1 has shown less toxicity against PGPRs as compared to acephate. The experimental results for geometric parameters and values of peak position in IR spectra have found to match excellently with the computational studies performed by GAMESS software package. Theoretically, twelve new analogs of 1 were prepared and their comparative reactivity (HOMO–LUMO energy) and biodecomposition (on the basis of polarizability) is discussed. The online version of this article (doi:10.1007/s13205-015-0313-6) contains supplementary material, which is available to authorized users.