Synthesis and Toxicological Effect of Some New Pyrrole Derivatives as Prospective Insecticidal Agents against the Cotton Leafworm, Spodoptera littoralis (Boisduval)

Antar A Abdelhamid; Kaoud S M Salama; Ahmed M Elsayed; Mohamed A Gad; Mahmoud Abd El Aleem Ali Ali El-Remaily

doi:10.1021/acsomega.1c05049

Synthesis and Toxicological Effect of Some New Pyrrole Derivatives as Prospective Insecticidal Agents against the Cotton Leafworm, Spodoptera littoralis (Boisduval)

ACS Omega. 2022 Jan 25;7(5):3990-4000. doi: 10.1021/acsomega.1c05049. eCollection 2022 Feb 8.

Authors

Antar A Abdelhamid^{1

2}, Kaoud S M Salama¹, Ahmed M Elsayed¹, Mohamed A Gad³, Mahmoud Abd El Aleem Ali Ali El-Remaily¹

Affiliations

¹ Department of Chemistry, Faculty of Science, Sohag University,82524 Sohag, Egypt.
² Chemistry Department, Faculty of Science, Albaha University, Albaha 1988, Saudi Arabia.
³ Research Institute of Plant Protection, Agriculture Research Center, 12112 Giza, Egypt.

Abstract

Herein, a series of biologically active pyrrole derivatives, namely 2-[(3-cyano-5-aryl-1H-pyrrol-2-yl)thio]acetic acids 2a-c, 2-[(2-hydroxyethyl)-thio]-5-aryl-1H-pyrrole-3-carbonitriles 3a-c, and 2-[(2-amino-ethyl)thio]-5-aryl-1H-pyrrole-3-carbonitriles 4a-c, 2,2'-disulfanediylbis(5-aryl-1H-pyrrole-3-carbonitriles) 5a-c, 2-((3-cyano-5-aryl-1H-pyrrol-2-yl)thio)acetates 6a-c, 2-[(3-cyano-5-phenyl-1H-pyrrol-2-yl)thio]acetohydrazides 7a-c, and 2-{2-[(3-cyano-5-aryl-1H-pyrrol-2-yl)thio]acetyl}-N-phenyl-hydrazinecarbothioamides 8a-c, as insecticidal agents, were synthesized via adaptable, smoothly accessible 2-(2-oxo-2-arylylethyl)malononitriles 1a-c. The structures were proved using infrared (IR), nuclear magnetic resonance (NMR), and mass spectrum (MS) techniques. Under laboratory conditions, the toxicological characteristics were tested towards Spodoptera littoralis, cotton leafworm insect type. In respect to the LC₅₀ values, compounds 6a, 7a, 8c, and 3c possess the highest insecticidal bioefficacy, with values of 0.5707, 0.1306, 0.9442, and 5.883 ppm, respectively. The study paves the way towards discovering new materials for potential use as insecticidal active agents.