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. 2022 May 5;12(22):13628-13638.
doi: 10.1039/d2ra02388a.

Synthesis, SAR studies, and insecticidal activities of certain N-heterocycles derived from 3-((2-chloroquinolin-3-yl)methylene)-5-phenylfuran-2(3 H)-one against Culex pipiens L. larvae

Sayed K Ramadan  1 , Doaa R Abdel Haleem  2 , Hisham S M Abd-Rabboh  3 , Nourhan M Gad  1 , Wael S I Abou-Elmagd  1 , David S A Haneen  1
Affiliations

Synthesis, SAR studies, and insecticidal activities of certain N-heterocycles derived from 3-((2-chloroquinolin-3-yl)methylene)-5-phenylfuran-2(3 H)-one against Culex pipiens L. larvae

Sayed K Ramadan et al. RSC Adv. .

Abstract

An acid hydrazide derivative was synthesized and transformed into a variety of valuable N-heterocycles such as pyridazinone, oxadiazole, triazolopyridazinone, and triazole derivatives via reactions with certain carbon electrophiles such as 4-methoxybenzaldehyde, indole-3-carbaldehyde, pentan-2,4-dione, and carbon disulfide. The chemical structures of all prepared compounds were verified via their analytical and spectroscopic data. The insecticidal activity of the N-heterocycles was evaluated against field and lab strains of the third larval instar of Culex pipiens. All tested compounds exhibited higher larvicidal activity against the lab strains compared to the field strains, with dissimilar ratios. The obtained results demonstrate that the high toxicity achieved by oxadiazole followed the order of furanone, pyridazinone and hydrazide, with lower LC50 values of the hydrazone and N-acetylpyridazinone derivatives compared to that of imidacloprid. Interestingly, these compounds are promising agents for insect pest control, especially since they are insoluble in water and can overcome the disadvantages of neonicotinoid applications in pest management programs.

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Conflict of interest statement

No potential conflict of interest was reported by the author(s).

Figures

Fig. 1
Fig. 1. Some quinoline-based drugs.
Scheme 1
Scheme 1. Reactions of the hydrazide 2 with certain carbonyl compounds.
Scheme 2
Scheme 2. Reactions of the hydrazide 2 with carbon disulfide under different conditions.
Fig. 2
Fig. 2. % Mortality of the lab strain of Culex pipiens larvae observed after 24 h of treatment at different concentrations of 1, 2, 3, 5, 6, 7, and IMI.
Fig. 3
Fig. 3. % Mortality of the lab strain of Culex pipiens larvae observed after 48 h of treatment at different concentrations of 1, 2, 3, 5, 6, 7, and IMI.
Fig. 4
Fig. 4. % Mortality of a field strain of Culex pipiens larvae observed after 24 h of treatment at different concentrations of 1, 2, 3, 5, 6, 7, and IMI.
Fig. 5
Fig. 5. % Mortality of a field strain of Culex pipiens larvae observed after 48 h of treatment at different concentrations of 1, 2, 3, 5, 6, 7, and IMI.
See this image and copyright information in PMC

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