Computational Chemistry studies of some cyano(3-phenoxyphenyl) methyl isobutyrate derived insecticides and molecular design of novel ones
Keywords:Insecticides; toxicity, design of isobutyrate derived insecticides
Communication in Physical Sciences 2020, 5(4): 455-469
Received 12 June 2020/Accepted 28 July 2020
This work was designed to study some isobutyrate derived insecticides (using computational chemistry) and to designed novels ones using quantitative structure activity relationship (QSAR) model. PM 7 quantum chemical descriptors were calculated for cyhalothrin (CYH), fenpropathrin (FEP), cypermethrin (CYP), deltamethrin (DEL), permethrin (PEM) and cyfluthrin (CYF). Calculated descriptors were frontier molecular energies (including the energy of the highest occupied molecular orbital (EHOMO), the energy of the lowest unoccupied molecular orbital (ELUMO) and the energy gap (DE)), the binding energy (EBind), the electronic energy (EElect), the hydration energy (EHyd) and logP. Those descriptors that exhibited excellent correlations with the experimental LD50 values (of the studied insecticides) were used to derive quantitative structure activity relationship (QSAR). Correlation between the theoretical and experimental LD50 values was excellent (R2 = 0.9500). The active sites of reactivity for the insecticides were identified through Fukui function analysis and were supported by their HOMO and LUMO diagrams. Based on the derived quantitative structure activity relationship, eleven (11) novel insecticides were designed and their theoretical activities (which ranged from 1319 to 5630 mg/kg) were comparable and better (in some cases) to the known insecticides. Therefore, quantitative structure activity approached can be effective in molecular design and modelling of insecticides
Ameh, P. O. & Eddy, N. O. (2018). Theoretical and Experimental Investigations of the Corrosion Inhibition Action of Piliostigma Thonningii Extract on Mild Steel in Acidic Medium. Communication in Physical Sciences, 3, 1, pp. 27-42.
Bendjeddou, A., Abbaz, T., Maache, S., Rehamnia, R., Gouasmia, A. K. & Villemin, D. (2016). Quantum chemical descriptors of some paminophenyl tetrathiafulvalenes through density functional theory (dft). Rasayan Journal, 9, 1, pp. 18-26
Can A.(2014). Quantitative structure-toxicity relationship (QSTR) studies on the organophosphate insecticides. Toxological Letters,
Devillers, J. & Devillers, H. (2009). Prediction of acute mammalian toxicity from QSARs and interspecies correlations. SAR QSAR. Environmental Research, 20, 5-6, 467–500.
Eddy NO & Ita BI (2011a) Theoretical and experimental studies on the inhibition potentials of aromatic oxaldehydes for the corrosion of mild steel in 0.1 M HCl. Journal of Molecular Modelling 17, 4, pp. 633-647.
Eddy, N. O. & Ita, , B. I. (2011b). Experimental and theoretical studies on the inhibition potentials of some derivatives of cyclopenta-1,3-diene. International Journal of Quantum Chemistry, 111, 14, pp. 3456-3473.
Eddy, N. O. & Ita, B. I. (2011). QSAR, DFT and quantum chemical studies on the inhibition potentials of some carbozones for the corrosion of mild steel in HCl. Journal of Molecular Modelling, 17, 2, pp. 359–376.
Eddy, N. O. & Essien, N. B. (2017). Computational chemistry study of toxicity of some m-tolyl acetate derivatives insecticides and molecular design of structurally related products. In Silico Pharmacology, 5, 1, pp. 14, doi:10.1007/s40203-017-0036-y.
Eddy, N. O. (2011). Experimental and theoretical studies on some amino acids and their potential activity as inhibitors for the corrosion of mild steel, Part 2. Journal of Advanced Research, 2, pp. 2:35–47. Doi: 10.1016/j.jare.2010.08.005.
Eddy, N. O., Ameh, P. O. & Essien N B. (2015). Experimental and computational chemistry studies on the inhibition of aluminium and mild steel in 0.1 M HCl by 3-nitrobenzoic acid. Journal of Taibah University for Science, DOI: 10.1080/16583655.2018.1500514
Eddy, N. O., Ita, B. I., Ibisi, N. E. & Ebenso, E. E. (2011). Experimental and quantum chemical studies on the corrosion inhibition potentials of 2-(2-oxoindolin-3-ylideneamino) acetic acid and indoline-2,3-dione. International Journal of Electrochemistry, 6, pp.1027-1044
Eddy, N. O., Momoh-Yahaya, H. & Oguzie, E. E.(2015). Theoretical and experimental studies on the corrosion inhibition potentials of some purines for aluminum in 0.1 M HCl. Journal of Advanced Research, 6, pp. 203–216. doi: 10.1016/j.jare.2014.01.004.
Hodgston E (2004) A textbook of modern toxicology. Wiley-interscience. 3rd edition. New York
Iwamura, H., Nishimura, K. & Fujita T. (1985) Quantitative structure-activity relationships of insecticides and plant growth regulators: comparative studies toward understanding the molecular mechanism of action. Environmental Health Perspective, 61, pp. 61:307–320. doi: 10.1289/ehp.8561307.
Jian, L., Yanging, G., Shibin, S., Xiaoping, R., Jie, S. & Zongde, W. (2014). Synthesis and quantitative structure-activity relationship (QSAR) studies of novel rosin-based diamide insecticides. RSC Advances, 4, pp. 58190-58199. doi: 10.1039/c3ra45801f.
Karelson, M. & Lobanov, V. S. (1996). Quantum-chemical descriptors in QSAP/QSPR studies. Chem. Rev. 96(3): 1027-1044.
Kikuchi, O. (1987) Systematic QSAR procedures with quantum chemical descriptors
Molecular Informatics, 6, 4, pp. 179-184.
Naik, P. K., Alam, A., Malhotra, A. & Rizvi O. (2010). Molecular modeling and structure-activity relationship of podophyllotoxin and its congeners. Journal of Biomedical Screening, 15, 5, pp. 528–540.
Naik, P. K., Singh, T. & Singh, H. (2009). Quantitative structure-activity relationship (QSAR) for insecticides: development of predictive in vivo insecticide activity models. SAR/QSAR Environmental Research, 20, 5-6, pp. 551–556.
Netzeva, T. I., Worth, A., Aldenberg, T., Benigni, R., Cronin, M.T.D., Gramatica, P., Jaworska, J.S., Scott, Kahn, S., Klopman, G., Carol, A., Marchant, C.A., Myatt, G., Nikolova-Jeliazkova, N., Patlewicz, G.Y., Perkins, R., Roberts, D.W., Schultz, T.W., Stanton, D.T., van de Sandt, J.J. M., Tong, W., Veith, G., &Yang, C. (2005) Current status of methods for defining the applicability domain of (quantitative) structure–activity relationships: the report and recommendations of ECVAM workshop 52. Altern Lab Anim, 33, 2, pp. 155–173
Vikas, R. (2015) Exploring the role of quantum chemical descriptors in modeling acute toxicity of diverse chemicals to Daphnia magna. Journal of Molecular Graphics and Modelling, 61, pp. 61:89–101. doi: 10.1016/j.jmgm.2015.06.009.
Copyright (c) 2020 The Journal and the author
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.