Dataset Information

Synthesis, molecular modelling and evaluation of larvicidal efficacy of annulated Benzo[h]chromenes against Culex pipiens L. Larvae.

ABSTRACT: A new series of substituted benzo[h]chromene, benzochromenopyrimidine, and benzochromenotriazolopyrimidine derivatives were synthesized via chemical transformations of iminonitrile, ethoxymethylene amino, and cyanomethylene functionalities. The chemical structures of the synthesized compounds were assured by spectroscopic data and elemental analysis. The larvicidal efficacy of these compounds against Culex pipiens L. larvae was investigated, revealing potent insecticidal activity, particularly for compounds 6, 10, and 16, exceeding that of the standard insecticide chlorpyrifos. The mode of action of these compounds was explored through molecular docking studies, indicating their potential as acetylcholine esterase (AChE) inhibitors and nicotinic acetylcholine receptors (nAChR) blockers. The structure-activity relationship analysis highlighted the influence of substituents and fused heterocyclic rings on larvicidal potency. These findings suggest that the synthesized compounds hold promise as potential candidates for developing novel and effective mosquito control agents.

SUBMITTER: El-Sayed MKF

PROVIDER: S-EPMC11310521 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Synthesis, molecular modelling and evaluation of larvicidal efficacy of annulated Benzo[h]chromenes against Culex pipiens L. Larvae.

El-Sayed Mahmoud K F MKF Elshahawi Manal M MM Abu El-Azm Fatma S M FSM Hosni Eslam M EM Kamal Mahmoud M Ali Yasmeen M YM

Scientific reports 20240808 1

A new series of substituted benzo[h]chromene, benzochromenopyrimidine, and benzochromenotriazolopyrimidine derivatives were synthesized via chemical transformations of iminonitrile, ethoxymethylene amino, and cyanomethylene functionalities. The chemical structures of the synthesized compounds were assured by spectroscopic data and elemental analysis. The larvicidal efficacy of these compounds against Culex pipiens L. larvae was investigated, revealing potent insecticidal activity, particularly f ...[more]

PMID: 39117743

Similar Datasets

Project description:Mosquitoes are unquestionably the most medic arthropod vectors of disease. Culex pipiens, usually defined as a common house mosquito, is a well-known carrier of several virus diseases. Crude ethanol extracts of different organs of Agratum houstonianum are tested with Culex pipiens Linnaeus (Diptera: Culicidae) to determine their larvicidal, antifeedant, and repellency effects. Alongside biochemical analysis, the activity of the AChE, ATPase, CarE, and CYP-450 is detected in the total hemolymph of the C. pipiens larvae to examine the enzymatic action on the way to explain their neurotoxic effect and mode of action. Through HPLC and GC–MS analysis of the phytochemical profile of A. houstonianum aerial parts is identified. The larvicidal activity of aerial parts; flower (AF), leaf (AL), and stem (AS) of A. houstonianum extracts are evaluated against the 3rd instar larvae of C. pipiens at 24-, 48- and 72-post-treatment. A. houstonianium AF, AL, and AS extracts influenced the mortality of larvae with LC50 values 259.79, 266.85, and 306.86 ppm, respectively after 24 h of application. The potency of AF and AL extracts was 1.69- and 1.25-folds than that of AS extract, respectively. A high repellency percentage was obtained by AF extract 89.10% at a dose of 3.60 mg/cm2. A. houstonianium AF prevailed inhibition on acetylcholinesterase and decrease in carboxylesterase activity. Moreover, a significant increase in the ATPase levels and a decrease in cytochrome P-450 monooxegenase activity (− 36.60%) are detected. HPLC analysis prevailed chlorogenic and rosmarinic acid as the major phenolic acids in AL and AF, respectively. GC–MS analysis of A. houstonianum results in the identification of phytol as the major makeup. Precocene I and II were detected in AF. Linoleic, linolenic, and oleic acid were detected in comparable amounts in the studied organs. Overall, results suggest that the A. houstonianum flower extract (AF) exhibits significant repellent, antifeedant, and larvicidal activities.

Project description:Mosquito control in Egypt depends on applying chemical synthetic pesticides that impact negatively on human health and the environment as well as the development of antibiotic and chemical resistance. This study aims to control the 3rd and 4th instars of Culex pipiens larvae using four bacterial strains. According to Phenotypic and molecular identification, the four isolates were identified as Bacillus subtilis MICUL D2023, Serratia marcescens MICUL A2023, Streptomyces albus LARVICID, and Pseudomonas fluorescens MICUL B2023. All strains were deposited in GenBank under accession numbers OQ764791, OQ729954, OQ726575, and OQ891356, respectively. Larvicidal activity of all microbial strain metabolites against a field strain of C. pipiens explored low LC50 results and reached its lowest values on the 3rd day with values of 6.40%, 38.4%, and 46.33% for P. fluorescens, S. albus, and S. marcescens, respectively. In addition, metabolites of P. fluorescence were more toxic than those of S. albus, followed by S. marcescens. B. subtilis shows no larvicidal effect on both field and lab mosquito strains. Microscopic alterations of 3rd and 4th instars showed toxic effects on different body parts (thorax, midgut, and anal gills), including losing external hairs, abdominal breakage, and larvae shrinkage, as well as different histological malformations in the digestive tract, midgut, and cortex. GC-MS analysis detected 51, 30, and 32 different active compounds from S. albus, S. marcescens, and P. fluorescens, respectively. GC detected 1, 2-BENZEA2:A52NEDICARBOXYLIC ACID, 2-Cyclohexene-1-carboxylic-acid-5-2-butenyl-methyl ester, and 3 octadecahydro2R3S4Z9Z-11R-12S from S. albus, S. marcesens, and P. fluorescens, respectively. Total protein, Total carbohydrate, and Acetylcholine esterase activity indicated significantly low levels on the 3rd day. All strain metabolites were safe against HSF cell lines. The docking results confirmed the role of the produced metabolites as larvicidal agents and Acetylcholine esterase inhibition. Such a problem need more studies on applying more and more natural pesticides.

Project description:Mosquitoes are one of the deadliest and most hazardous animals on Earth, where they transmit several diseases that kill millions of people annually. There is an ongoing search almost everywhere in the world for more effective and contemporary ways to control mosquitoes other than pesticides. Phytochemicals are affordable, biodegradable biological agents that specialize in eliminating pests that represent a risk to public health. The effectiveness of Acacia nilotica methanol and aqueous leaf extracts against 4th instar larvae was evaluated. The results revealed that the methanol extract of A. nilotica had a noticeable influence on the mortality rate of mosquito larvae, especially at high concentrations. Not only did the mortality rate rise significantly, but the hatching of the mosquito eggs was potentially suppressed.Terpenes, fatty acids, esters, glycosides, pyrrolidine alkane, piperazine, and phenols were the most prevalent components in the methanol extract, while the aqueous extract of A. nilotica exclusively showed the presence of fatty acids. The insecticidal susceptibility tests of both aqueous and alcoholic extract of A. nilotica confirmed that the Acacia plant could serves as a secure and efficient substitute for chemical pesticides because of its promising effect on killing larvae and egg hatching delaying addition to their safety as one of the natural pesticides. Molecular docking study was performed using one of the crucial and life-controlling protein targets, fatty acid binding protein (FABP) and the most active ingredients as testing ligands to describe their binding ability. Most of the structurally related compounds to the co-crystallized ligand, OLA, like hexadecanoic acid furnished high binding affinity to the target protein with very strong and stable intermolecular hydrogen bonding and this is quite similar to OLA itself. Some other structural non-related compounds revealed extraordinarily strong binding abilities like Methoxy phenyl piperazine. Most of the binding reactivities of the majortested structures are due to high structure similarity between the positive control, OLA, and tested compounds. Such structure similarity reinforced with the binding abilities of some detected compounds in the A. nilotica extract could present a reasonable interpretation for its insecticidal activity via deactivating the FABP protein. The FABP4 enzyme inhibition activity was assessed for of both methanolic and aqueous of acacia plant extract and the inhibition results of methanol extract depicted noticeable potency if compared to orlistat, with half-maximal inhibitory concentration (IC50) of 0.681, and 0.535 µg/ml, respectively.

Project description:Mosquitoes can transmit the terrible diseases to human beings. Soil-borne fungal products act as potential source for low-cost chemicals, used for developing eco-friendly control agents against mosquito-vector borne diseases. The prime aim of study was to check the larvicidal potential of fungus mycelia (by ethyl acetate solvent) extract from Penicillium daleae (KX387370) against Culex quinquefasciatus and Aedes aegypti and to test the toxicity of brine shrimp Artemia nauplii, by observing the physiological activity. The ethyl acetate extract of P. daleae mycelia (after 15 days) from Potato dextrose broth (PDB) medium revealed better result with least LC50 and LC90 values of I-IV instars larvae of Cx. quinquefasciatus (LC50 = 127.441, 129.087, 108.683, and 93.521; LC90 = 152.758, 158.169, 139.091, and 125.918 μg/ml) and Ae. aegypti (LC50 = 105.077, 83.943, 97.158, and 76.513; LC90 = 128.035, 106.869, 125.640, and 104.606 μg/ml) respectively. At higher concentration (1000 μg/ml) of extracts, mortality begins at 18 h of exposure and attained 100% mortality after 48 h exposure. Overall, the activity was depends on the dose and time of exposure to the extracts. The stereomicroscopic and histopathological analysis of Ae. aegypti and Cx. quinquefasciatus larvae treated with mycelium ethyl acetate extract showed complete disintegration of abdominal region, particularly the midgut and caeca, loss of cuticular parts and caudal hairs. Morphological characterization of the fungi was performed and taxonomically identified through 5.8s rDNA technique. The phylogenetic analysis of rDNA sequence was carried out to find out the taxonomic and the evolutionary sketch of isolate in relation to earlier described genus Penicillium. Behavior and swimming speed alteration was analyzed together with mortality. The results of the experiment indicates that swimming behavior recorder (SBR) is a appropriate tool to detect individual swimming speed of the A. nauplii organisms, since the values have been obtained in accordance with control monitored results showed the 2.75 mm s-1 and after 24 h treated found to be 0.72 mm s-1, respectively. The extract-exposed to A. nauplii showed changes in body structures, i.e., intestine enlargement, eye formation, outer shell malformations and loss of antennae. In the present study, we aimed to investigate the toxicity of the ethyl acetate extract of P. daleae on A. nauplii larvae by performing the mortality, behavior and alterations in swimming responses. This is the first time report on the larvicidal efficacy of P. daleae ethyl acetate extract against Cx. quinquefasciatus and Ae. aegypti larvae.

Dataset Information

Synthesis, molecular modelling and evaluation of larvicidal efficacy of annulated Benzo[h]chromenes against Culex pipiens L. Larvae.

Publications

Synthesis, molecular modelling and evaluation of larvicidal efficacy of annulated Benzo[h]chromenes against Culex pipiens L. Larvae.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets