Larvicidal Activity of Geranylacetone Derivatives against Culex quinquefasciatus Larvae and Investigation of Environmental Toxicity and Non-Target Aquatic Species

A grindstone method based on Mannich condensation was used to synthesize geranylacetone derivatives (1a–1f). The method showed a high yield under milder reaction conditions. Analyses of the synthesized compounds were carried out by FTIR, 1...

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Autores principales:	Mohammed Al-Zharani, Mohammed S. Al-Eissa, Hassan A. Rudayni, Daoud Ali, Saud Alarifi, Radhakrishnan Surendrakumar, Akbar Idhayadhulla
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	Mannich base geranylacetone grindstone chemistry Green Chemistry approach larvicidal activity <i>Culex quinquefasciatus</i> Agriculture S
Acceso en línea:	https://doaj.org/article/ee84f99908324848ab0c5d3ea423517f
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spelling	oai:doaj.org-article:ee84f99908324848ab0c5d3ea423517f2021-11-25T16:12:12ZLarvicidal Activity of Geranylacetone Derivatives against <i>Culex quinquefasciatus</i> Larvae and Investigation of Environmental Toxicity and Non-Target Aquatic Species10.3390/agronomy111123422073-4395https://doaj.org/article/ee84f99908324848ab0c5d3ea423517f2021-11-01T00:00:00Zhttps://www.mdpi.com/2073-4395/11/11/2342https://doaj.org/toc/2073-4395A grindstone method based on Mannich condensation was used to synthesize geranylacetone derivatives (<b>1a</b>–<b>1f</b>). The method showed a high yield under milder reaction conditions. Analyses of the synthesized compounds were carried out by FTIR, <sup>1</sup>H, <sup>13</sup>C NMR, mass spectrometry, and elemental analysis. We synthesized and evaluated the larvicidal and ichthyotoxic activities of six compounds (<b>1a</b>–<b>1f</b>) in this study. Compound <b>1f</b> (5,9-dimethyl-1-phenyl-3-(2-(3-phenylallylidene)hydrazinyl)deca-4,8-dien-1-one) was more active (LD<sub>50</sub>: 14.1 µg/mL) against the second instar larvae of <i>Culex quinquefasciatus</i> than geranylacetone (67.2 µg/mL), whereas the former caused 13.9% mortality at 100 µg/mL. Geranylacetone, in an antifeedant screening test, showed 53.1% against <i>Oreochromis mossambicus</i> within 24 h. The compound <b>1f</b> showed high larvicidal activity against <i>C. quinquefasciatus</i> and was non-toxic to non-target aquatic species.Mohammed Al-ZharaniMohammed S. Al-EissaHassan A. RudayniDaoud AliSaud AlarifiRadhakrishnan SurendrakumarAkbar IdhayadhullaMDPI AGarticleMannich basegeranylacetonegrindstone chemistryGreen Chemistry approachlarvicidal activity<i>Culex quinquefasciatus</i>AgricultureSENAgronomy, Vol 11, Iss 2342, p 2342 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Mannich base geranylacetone grindstone chemistry Green Chemistry approach larvicidal activity <i>Culex quinquefasciatus</i> Agriculture S
spellingShingle	Mannich base geranylacetone grindstone chemistry Green Chemistry approach larvicidal activity <i>Culex quinquefasciatus</i> Agriculture S Mohammed Al-Zharani Mohammed S. Al-Eissa Hassan A. Rudayni Daoud Ali Saud Alarifi Radhakrishnan Surendrakumar Akbar Idhayadhulla Larvicidal Activity of Geranylacetone Derivatives against <i>Culex quinquefasciatus</i> Larvae and Investigation of Environmental Toxicity and Non-Target Aquatic Species
description	A grindstone method based on Mannich condensation was used to synthesize geranylacetone derivatives (<b>1a</b>–<b>1f</b>). The method showed a high yield under milder reaction conditions. Analyses of the synthesized compounds were carried out by FTIR, <sup>1</sup>H, <sup>13</sup>C NMR, mass spectrometry, and elemental analysis. We synthesized and evaluated the larvicidal and ichthyotoxic activities of six compounds (<b>1a</b>–<b>1f</b>) in this study. Compound <b>1f</b> (5,9-dimethyl-1-phenyl-3-(2-(3-phenylallylidene)hydrazinyl)deca-4,8-dien-1-one) was more active (LD<sub>50</sub>: 14.1 µg/mL) against the second instar larvae of <i>Culex quinquefasciatus</i> than geranylacetone (67.2 µg/mL), whereas the former caused 13.9% mortality at 100 µg/mL. Geranylacetone, in an antifeedant screening test, showed 53.1% against <i>Oreochromis mossambicus</i> within 24 h. The compound <b>1f</b> showed high larvicidal activity against <i>C. quinquefasciatus</i> and was non-toxic to non-target aquatic species.
format	article
author	Mohammed Al-Zharani Mohammed S. Al-Eissa Hassan A. Rudayni Daoud Ali Saud Alarifi Radhakrishnan Surendrakumar Akbar Idhayadhulla
author_facet	Mohammed Al-Zharani Mohammed S. Al-Eissa Hassan A. Rudayni Daoud Ali Saud Alarifi Radhakrishnan Surendrakumar Akbar Idhayadhulla
author_sort	Mohammed Al-Zharani
title	Larvicidal Activity of Geranylacetone Derivatives against <i>Culex quinquefasciatus</i> Larvae and Investigation of Environmental Toxicity and Non-Target Aquatic Species
title_short	Larvicidal Activity of Geranylacetone Derivatives against <i>Culex quinquefasciatus</i> Larvae and Investigation of Environmental Toxicity and Non-Target Aquatic Species
title_full	Larvicidal Activity of Geranylacetone Derivatives against <i>Culex quinquefasciatus</i> Larvae and Investigation of Environmental Toxicity and Non-Target Aquatic Species
title_fullStr	Larvicidal Activity of Geranylacetone Derivatives against <i>Culex quinquefasciatus</i> Larvae and Investigation of Environmental Toxicity and Non-Target Aquatic Species
title_full_unstemmed	Larvicidal Activity of Geranylacetone Derivatives against <i>Culex quinquefasciatus</i> Larvae and Investigation of Environmental Toxicity and Non-Target Aquatic Species
title_sort	larvicidal activity of geranylacetone derivatives against <i>culex quinquefasciatus</i> larvae and investigation of environmental toxicity and non-target aquatic species
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/ee84f99908324848ab0c5d3ea423517f
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Larvicidal Activity of Geranylacetone Derivatives against <i>Culex quinquefasciatus</i> Larvae and Investigation of Environmental Toxicity and Non-Target Aquatic Species

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