RESUMEN
Certain 2-amino-6-alkoxy-4-arylpyridine-3,5-dicyanide 1a-e were prepared via a straightforward process using microwave technology rather than conventional methods. This involved reaction of arylidenemalononitrile thru propanedinitrile in the occurrence of sodium alkoxide under MW. While, their positional isomer 4-amino-6-alkoxy-2-arylpyridine-3,5-dicyanide 3a-j have been separated from the reaction of aryl aldehydes with 2-aminoprop-1-ene-1,1,3-tricarbonitrile 2 in the presence of sodium alkoxide using microwave technic. Furthermore, the insecticidal properties of all synthesized compounds were observed with respect to Cotton aphid nymphs and adults. Neonicotinoid pesticides are indicated as the most effective pesticides toward aphids and many other pests. Many insecticides are discovered as novelties. As a result, several pyridine compounds were chemical method synthesized to serve as equivalents of neonicotinoids, a broad class of insecticides. With LC50 value of 0.03â mg/L, components 3g exhibit the highest insecticidal bioactivity. This work discusses how to find new chemicals that could be used as insecticidal agents in the future.
Asunto(s)
Alcoholes , Áfidos , Insecticidas , Animales , Insecticidas/química , Microondas , Neonicotinoides/farmacología , Sodio/farmacologíaRESUMEN
5-(Cyanomethyl)-3-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)amino)-1H-pyrazole-4-carbonitrile (3) is used as a key for the synthesis of arylidenes 5a-fvia its reaction with some aldehydes 4a-f. 5-[(5,5-Dimethyl-3-oxocyclohex-1-en-1-yl)amino]-3-(2-imino-2H-chromen-3-yl)-1H-pyrazole-4-carbonitrile (7) was synthesized via the reaction of compound (3) with 2-hydroxybenzaldehyde in EtOH/piperidine. The target compounds were tested against cotton leafworm larvae in their second and fourth instar. The available data demonstrated that the LC50 values for commercial phenylpyrazole were 3.37 mg/L and 4.55 mg/L for the most affected synthesized compound, 5b. The chemical structure of compound 5b has two cyano moieties, a pyrazole ring and a chlorophenyl, which may be increasing it efficiency. Evaluation of the latent effects of the examined synthesized compounds on various biological parameters, including adult longevity, pupal weight, proportion of normal, deformed pupae, adult emergency, fecundity, and egg hatchability, was done in an additional effort to slightly improve insecticidal compounds. Twelve synthesized compounds were subjected to a molecular docking analysis against glutamate-activated chloride channels. Twelve artificial compounds with the PDB ID of 4COF were subjected to a molecular docking study against the gamma-aminobutyric acid receptor (GABA).
RESUMEN
Quinazoline compounds have gained significant attention in the fields of agriculture and chemistry due to their diverse activities. In this study, we focused on a series of quinazoline derivatives (4a-l). The objectives involved multiple aspects, including preparation, evaluation of their agricultural bioactivity against the maize aphid (Rhopalosiphum maidis), estimation of the structure-activity relationships (SAR), and conducting molecular docking analysis. The results of the agricultural bioactivities revealed that compound (4b) possesses the highest insecticidal activity, and the other compounds have good potential as insecticidal agents. We conducted the SARs and also molecular docking investigation to elucidate the binding modes and interactions of these compounds with target proteins relevant to the agricultural bioactivity. The docking results provided valuable information on the binding affinities and molecular interactions, aiding in the rationalization of the observed bioactivity trends. The enzyme, acetylcholinesterase (AChE), was docked with the 12 synthetic compounds (4a-l). Among these compounds, (4b), (4i), and (4e)exhibited the highest binding affinity, with docking scores (S) of -7.96, -7.83, and -7.73 kcal/mol, respectively. They were followed by compounds (4d) (S = -7.57 kcal/mol), (4c) (S = -7.53 kcal/mol), (4g) (S = -7.34 kcal/mol), (4f) (S = -7.23 kcal/mol), (4h) (S = -7.14 kcal/mol), (4k) (S = -6.61 kcal/mol), (4j) (S = -6.57 kcal/mol), (4a) (S = -6.28 kcal/mol), and finally (4l) (S = -6.01 kcal/mol). These compounds were shown to have a variety of binding interactions within the 2ACE active site, as evidenced by protein-ligand docking configurations. This study gives evidence that those compounds have AChE-inhibitory capabilities and, hence, may be used for AChE-targeting development. Also, the findings in this study highlight the potential of these compounds as agricultural agents and provide valuable insights for the design and development of some quinazoline derivatives with enhanced bioactivity for crop protection.
RESUMEN
Using ultrasound technology instead of traditional methods, some pyridine derivatives were prepared by a simple procedure via a four-component reaction of different aromatic aldehydes, acetyl aryl, sodium alkoxide, and malononitrile, and additionally, all prepared compounds were monitored for insecticidal activities toward nymphs and adults of cowpea aphid. Though a lot of insecticides are discovered as a novelty on the other hand, neonicotinoid compounds are reflected as the most affected insecticides against aphids and many other pests. Thus, some of the pyridine derivatives were chemically prepared as analogues to a large group of insecticides called neonicotinoids. Under laboratory conditions, the toxicity of these components was measured toward adults and nymphs of Aphis craccivora. With respect to the LC50 values, components 1f, 1d, and 1c have the utmost insecticidal bioactivity, with values of 0.080, 0.098, and 0.127 mg/L. This work covers the way to discover novel compounds for the prospective use as insecticidal representatives.