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

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>...

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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
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Acceso en línea:https://doaj.org/article/ee84f99908324848ab0c5d3ea423517f
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Sumario: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.