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Synthesis and Toxicological Effect of Some New Pyrrole Derivatives as Prospective Insecticidal Agents against the Cotton Leafworm, Spodoptera littoralis (Boisduval)
[Image: see text] 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(...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8829954/ https://www.ncbi.nlm.nih.gov/pubmed/35155894 http://dx.doi.org/10.1021/acsomega.1c05049 |
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author | Abdelhamid, Antar A. Salama, Kaoud S. M. Elsayed, Ahmed M. Gad, Mohamed A. Ali Ali El-Remaily, Mahmoud Abd El Aleem |
author_facet | Abdelhamid, Antar A. Salama, Kaoud S. M. Elsayed, Ahmed M. Gad, Mohamed A. Ali Ali El-Remaily, Mahmoud Abd El Aleem |
author_sort | Abdelhamid, Antar A. |
collection | PubMed |
description | [Image: see text] 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 LC(50) 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. |
format | Online Article Text |
id | pubmed-8829954 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-88299542022-02-11 Synthesis and Toxicological Effect of Some New Pyrrole Derivatives as Prospective Insecticidal Agents against the Cotton Leafworm, Spodoptera littoralis (Boisduval) Abdelhamid, Antar A. Salama, Kaoud S. M. Elsayed, Ahmed M. Gad, Mohamed A. Ali Ali El-Remaily, Mahmoud Abd El Aleem ACS Omega [Image: see text] 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 LC(50) 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. American Chemical Society 2022-01-25 /pmc/articles/PMC8829954/ /pubmed/35155894 http://dx.doi.org/10.1021/acsomega.1c05049 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Abdelhamid, Antar A. Salama, Kaoud S. M. Elsayed, Ahmed M. Gad, Mohamed A. Ali Ali El-Remaily, Mahmoud Abd El Aleem Synthesis and Toxicological Effect of Some New Pyrrole Derivatives as Prospective Insecticidal Agents against the Cotton Leafworm, Spodoptera littoralis (Boisduval) |
title | Synthesis and Toxicological Effect of Some New Pyrrole
Derivatives as Prospective Insecticidal Agents against the Cotton
Leafworm, Spodoptera littoralis (Boisduval) |
title_full | Synthesis and Toxicological Effect of Some New Pyrrole
Derivatives as Prospective Insecticidal Agents against the Cotton
Leafworm, Spodoptera littoralis (Boisduval) |
title_fullStr | Synthesis and Toxicological Effect of Some New Pyrrole
Derivatives as Prospective Insecticidal Agents against the Cotton
Leafworm, Spodoptera littoralis (Boisduval) |
title_full_unstemmed | Synthesis and Toxicological Effect of Some New Pyrrole
Derivatives as Prospective Insecticidal Agents against the Cotton
Leafworm, Spodoptera littoralis (Boisduval) |
title_short | Synthesis and Toxicological Effect of Some New Pyrrole
Derivatives as Prospective Insecticidal Agents against the Cotton
Leafworm, Spodoptera littoralis (Boisduval) |
title_sort | synthesis and toxicological effect of some new pyrrole
derivatives as prospective insecticidal agents against the cotton
leafworm, spodoptera littoralis (boisduval) |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8829954/ https://www.ncbi.nlm.nih.gov/pubmed/35155894 http://dx.doi.org/10.1021/acsomega.1c05049 |
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