Insecticidal potential of some Acephate derivatives and their quantitative structure-activity relationship (QSAR)

Sharifi, Mahboobeh; Memarizadeh, Nargess; Ghadamyari, Mohammad; Gholivand, Khodayar; Ebrahimi Valmoozi, Ali Asghar

doi:10.48311/jcp.2021.1559

Insecticidal potential of some Acephate derivatives and their quantitative structure-activity relationship (QSAR)

https://doi.org/10.48311/jcp.2021.1559

Volume 10, Issue 3
September 2021

Pages 585-596

Document Type : Original Research

Authors

M. Sharifi ¹

N. Memarizadeh ²

M. Ghadamyari ³

K. Gholivand ⁴

A. A. Ebrahimi Valmoozi ⁵

¹ Plant Protection Research Department, Golestan Agricultural and Natural Resources Research Center, Agricultural Research, Education and Extension Organization, Gorgan, Iran.

² Department of Pesticides Researches, Iranian Research Institute of Plant Protection, Agricultural Research, Education and Extension Organization (AREEO), Tehran, Iran.

³ Department of Plant Protection, Faculty of Agricultural Sciences, University of Guilan, Rasht, Iran.

⁴ Department of Chemistry, Tarbiat Modares University, Tehran, Iran.

⁵ Department of Advanced Materials and Nanotechnology, Imam Hossein University, Tehran, Iran.

Abstract

Organophosphates (OPs), one of the most important pesticide groups, are used worldwide to control pests. Acetylcholinesterase (EC 1.14.18.1) (AChE), an enzyme from insects’ nervous systems, is the leading target site of this group of pesticides, such as Acephate. Inhibition of enzyme activity through Acephate-derived compounds can control both resistant and non-resistant pests to OPs. In this research, the toxicity of these compounds was assayed regarding the control of Xanthogaleruca luteola (Muller). Results of the in vivo screening test revealed that two derived compounds of phosphorhydrazides (PHA) (i.e., NH₂-C(O) NH-NH P(O)(OC₆H₅) and OC₄H₃-C(O)NH-NHP(S)(OCH₃)₂) showed the most significant insecticidal potential. AChE was purified and isolated from the third instar larvae of elm leaf beetle, X. luteola, using affinity chromatography. IC₅₀ values, inhibition mechanisms, and inhibitory constant (Ki) of NH₂-C(O) NH-NH P(O)(OC₆H₅) and OC₄H₃-C(O)NH-NHP(S)(OCH₃)₂ as inhibitors were calculated for the purified AChE. These compounds inhibited acetylcholinesterase (AChE) and general esterases of third instar larvae of elm leaf beetle. These compounds, by mix inhibition mechanism, inhibited AChE enzyme, and K_i obtained was 1.16 and 0.88 µM^-1min^-1 for NH2-C(O) NH-NH P(O)(OC6H5) and OC4H3-C(O)NH-NHP(S)(OCH3)2, respectively. QSAR study based on multiple linear regressions (MLR) and principal component analysis (PCA) showed that the non-descriptor net charge of the nitrogen atom influenced by the polarization of N-H group had the most significant effect on the insecticidal potential. Therefore, designing new compounds that control the N-H polarization of the nitrogen atom could be an excellent option to study insecticidal properties of Acephate-derived compounds.

Keywords

QSAR study

Xanthogaleruca luteola

insecticide derivatives

phosphoramidate

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