Abstract
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.Electronic supplementary materialThe online version of this article (doi:10.1007/s13205-015-0313-6) contains supplementary material, which is available to authorized users.
Highlights
All the contaminants including insecticides, nematodes and herbicides applied to crops reach to soil and influence the soil fertility by inhibiting the soil’s microorganisms
By comparing the UV–Vis spectra of acephate with product (Fig. 1), it was observed that 1 contains an organic chromophoric group that leads to increase in wavelength as well as absorption
UV–Vis spectra clearly indicate the formation of product due to bond formation of phenylhydrazine with acephate
Summary
All the contaminants including insecticides, nematodes and herbicides applied to crops reach to soil and influence the soil fertility by inhibiting the soil’s microorganisms. Pesticides are considered to be an integral part of modern agriculture. The topics such as green decomposition, production of less toxic and green pesticides are the prime most requirements of current era. The insecticidal potency of acephate is due to the inhibition of acetyl-cholinesterase (AChE) activity (Kumar et al 2013a, 2015a). It is toxic in various components of the environment and further decomposed into highly toxic methamidophos (Kumar et al 2015a). The safe decomposition and preparation of less toxic analog of acephate are an important issue from the environmental concern
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