Design, Synthesis, and Biological Activities of Novel Coumarin Derivatives as Pesticide Candidates

Scaffold structures, new mechanisms of action, and targets present enormous challenges in the discovery of novel pesticides. The discovery of new scaffolds is the basis for the continuous development of modern agrochemicals. Identification of a good scaffold such as triazole, carbamate, methoxy acrylate, pyrazolamide, pyrido-pyrimidinone mesoionic, and bisamide often leads to the development of a new series of pesticides. In addition, pesticides with the same target, including the inhibitors of succinate dehydrogenase (SDH), oxysterol-binding-protein, and p-hydroxyphenyl pyruvate dioxygenase (HPPD), may have the same or similar scaffold structure. Recent years have witnessed significant progress in the discovery of new pesticides using natural products as scaffolds or bridges. In recent years, there have been increasing reports on the application of natural benzopyran compounds in the discovery of new pesticides, especially osthole and coumarin. A systematic and comprehensive review of benzopyran active compounds in the discovery of new agricultural chemicals is helpful to promote the discussion and development of benzopyran active compounds. Therefore, this work systematically reviewed the research and application of benzopyran derivatives in the discovery of agricultural chemicals, summarized the antiviral, herbicidal, antibacterial, fungicidal, insecticidal, nematicidal and acaricidal activities of benzopyran active compounds, and discussed the structural−activity relationship and mechanism of action. In addition, some active fragments were recommended to further optimize the chemical structure of benzopyran active compounds based on reference information.

Section: Introductionmentioning

confidence: 99%

Recent Advances and Outlook of Benzopyran Derivatives in the Discovery of Agricultural Chemicals

Liu,

Zhang,

Zou

et al. 2024

“…However, the extensive and unregulated use of these traditional chemical pesticides has had grave implications. This includes a substantial increase in pesticide residues, which can be harmful to humans and the environment . Furthermore, excessive usage of these compounds has contributed to the development of drug resistance in pests, limiting the efficacy of these pesticides.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Acaricidal/Insecticidal Activities of New Phenylpyrazole Derivatives Comprising an Imide Moiety

Liu,

Ye,

Gao

et al. 2024

Using nicofluprole as the lead compound, we designed and synthesized a series of new phenylpyrazole analogues through substituting the methyl group on the nitrogen atom of the amide with an acyl group. Bioassay results showed that compounds A12−A17 with a 1-cyanocyclopropimide group exhibited outstanding insecticidal activity. The LC 50 values for compounds A12−A17 against Tetranychus cinnabarinus ranged from 0.58 to 0.91 mg/L. Compound A15 showed an LC 50 value of 0.29 and 3.10 mg/L against Plutella xylostella and Myzus persicae, respectively. Molecular docking indicated the potential binding interactions of compound A15 with a gamma-aminobutyric acid receptor. Additionally, density functional theory calculations implied that the 1-cyanocyclopropimide structure might be essential for its biological activity. Phenylpyrazole derivatives, containing a 1-cyanocyclopropimide fragment, have the potential for further development as potential insecticides.

“…Owing to their impressive structural diversity, various desirable bioactivities, and good biocompatibility and biodegradability, natural products have proven to be valuable sources of compounds for drug and pesticide development. − Flavonols, naturally occurring secondary metabolites, belong to a subgroup of flavonoids with 3-hydroxyflavone backbone, and they are widely distributed in plant foods and have a wide range of pharmacological activities, including antibacterial, antifungal, antiviral, anticancer, antioxidant, and anti-inflammatory effects (Figure ). Hydrazides are extensively employed as active fragments for structural modification of agrochemical-related compounds.…”

Section: Introductionmentioning

confidence: 99%

Discovery of Novel Acethydrazide-Containing Flavonol Derivatives as Potential Antifungal Agents

Chen,

Jiang,

Tong

et al. 2024

In this study, a series of novel hydrazide-containing flavonol derivatives was designed, synthesized, and evaluated for antifungal activity. In the in vitro antifungal assay, most of the target compounds exhibited potent antifungal activity against seven tested phytopathogenic fungi. In particular, compound C32 showed the best antifungal activity against Rhizoctonia solani (EC 50 = 0.170 μg/mL), outperforming carbendazim (EC 50 = 0.360 μg/mL) and boscalid (EC 50 = 1.36 μg/mL). Compound C24 exhibited excellent antifungal activity against Valsa mali, Botrytis cinerea, and Alternaria alternata with EC 50 values of 0.590, 0.870, and 1.71 μg/ mL, respectively. The in vivo experiments revealed that compounds C32 and C24 were potential novel agricultural antifungals. 3D quantitative structure−activity relationship (3D-QSAR) models were used to analyze the structure−activity relationships of these compounds. The analysis results indicated that introducing appropriate electronegative groups at position 4 of a benzene ring could effectively improve the anti-R. solani activity. In the antifungal mechanism study, scanning electron microscopy and transmission electron microscopy analyses revealed that C32 disrupted the normal growth of hyphae by affecting the structural integrity of the cell membrane and cellular respiration. Furthermore, compound C32 exhibited potent succinate dehydrogenase (SDH) inhibitory activity (IC 50 = 8.42 μM), surpassing that of the SDH fungicide boscalid (IC 50 = 15.6 μM). The molecular dynamics simulations and docking experiments suggested that compound C32 can occupy the active site and form strong interactions with the key residues of SDH. Our findings have great potential for aiding future research on plant disease control in agriculture.