Discovery of Trifluorobutene Amide Derivatives as Potential Nematicides: Design, Synthesis, Nematicidal Activity Evaluation, SAR, and Mode of Action Study

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(3), С. 1429 - 1443

Опубликована: Янв. 8, 2024

Plant-parasitic nematodes are one of the major threats to crop protection. However, only limited nematicides currently available and confronted with a growing resistance problem, which necessitates development novel nematicides. In this study, series trifluorobutene amide derivatives was synthesized through strategy bond reversal, their nematicidal activity against Meloidogyne incognita evaluated. The bioassay showed that compounds C2, C10, C18 some analogues thereof exhibited good activity. Among them, compound C2 containing benzene ring [C26 (R = 2-CH3) C33 2-Cl)] excellent bioactivity M. in vitro. LC50/72h values reached 14.13 14.71 mg·L–1, respectively. Moreover, C10 thiophene [C43 5-CH3), C44 4-CH3), C50 5-Cl)] significant vivo inhibition rates 68.8, 65.5, 69.8% at 2.5 mg·L–1 matrix, Meanwhile, also control effects both cups microplots. structure–activity relationship (SAR) discussed detail. Comparative molecular field analysis (CoMFA) conducted develop SAR profile. preliminary mode action investigation strong on egg hatching, motility, feeding behavior, growth Caenorhabditis elegans. At same time, impact active biochemical indicators related oxidative stress influenced production ROS (reactive oxygen species), accumulation lipofuscin lipids C.

Язык: Английский

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Design, Synthesis, and Bioactivity of Trifluoroethylthio-Substituted Phenylpyrazole Derivatives

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(21), С. 11949 - 11957

Опубликована: Май 17, 2024

As the first marketed phenylpyrazole insecticide, fipronil exhibited remarkable broad-spectrum insecticidal activity. However, it poses a significant threat to aquatic organisms and bees due its high toxicity. Herein, 35 derivatives containing trifluoroethylthio group on 4 position of pyrazole ring were designed synthesized. The predicted physicochemical properties all compounds within reasonable range. biological assay results revealed that compound

Язык: Английский

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Discovery of Novel Neonicotinoids with Conjugated Diene Enabled by Cascade Allylation/Isomerization Synthetic Methodology

Journal of Agricultural and Food Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 22, 2025

As one of the most significant insecticides, neonicotinoids have played a pivotal role in crop protection and public sanitation. However, high resistance bee toxicity neonicotinoid insecticides attracted considerable attention. Herein, series compounds with conjugated diene moieties were synthesized through cascade allylation/isomerization reaction. Most target exhibited excellent insecticidal activities against Aphis craccivora, some good Mythimna separata. In particular, compound A15 showed outstanding activity A. craccivora (LC50 = 0.15 mg/L), which was superior to that imidacloprid 0.36 mg/L). addition, this candidate minimal cross-resistance imidacloprid. The acute contact tests on Apis mellifera suggested 10 times less toxic than Electrophysiological experiments molecular docking studies indicated exerted its effects by interfering nicotinic acetylcholine receptors. This work identifies novel potential for further development.

Язык: Английский

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Design, Synthesis, Nematicidal Activity Evaluation, and Mode of Action Study of Novel Trifluorobutene Ester Derivatives as Potential Nematicides

Journal of Agricultural and Food Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 23, 2025

Crop protection globally is under threat from infections caused by plant-parasitic nematodes (PPNs). PPNs can wreak havoc on agricultural production. However, only limited nematicides are currently available, and the growing resistance problem a concern; therefore, novel urgently needed. Thirty-three trifluorobutene ester derivatives were synthesized, then their biological activity against Meloidogyne incognita was tested in this study. Among them, nine compounds exhibited excellent vitro bioactivity M. incognita; LC50/72h values reached 1.77-3.95 mg/L. In addition, derivative of active compound above containing piperazine ring significant vivo with an inhibition rate 77.3% at 1.25 mg/L matrix. The structure-activity relationships (SARs) all synthesized analyzed, further comparative molecular field analysis (CoMFA) calculated to discuss SAR profile. preliminary mechanisms action study suggested that some had great inhibitory effect egg hatching, motility, feeding ability, growth Caenorhabditis elegans. Meanwhile, effects biochemical indices related oxidative stress indicated two could significantly promote induce toxicity through damage.

Язык: Английский

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Discovery of Trisubstituted N-Phenylpyrazole Containing Diamides with Improved Insecticidal Activity

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(14), С. 8072 - 8080

Опубликована: Март 28, 2024

To increase the structural diversity of insecticides and meet needs effective integrated insect management, structure chlorantraniliprole was modified based on a previously established three-dimensional quantitative structure–activity relationship (3D-QSAR) model. The pyridinyl moiety in replaced with 4-fluorophenyl group. Further modifications this group by introducing halogen atom at position 2 an electron-withdrawing (e.g., iodine, cyano, trifluoromethyl) 5 led to 34 compounds good insecticidal efficacy against Mythimna separata, Plutella xylostella, Spodoptera frugiperda. Among them, compound IV f M. separata showed potency comparable that chlorantraniliprole. p P. xylostella displayed 4.5 times higher than In addition, d exhibited potencies S. Transcriptome analysis molecular target is ryanodine receptor. Molecular docking further performed verify mode action activity resistant xylostella.

Язык: Английский

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Effects of anthranilic diamide insecticides on metamorphosis in the common toad Rhinella arenarum (Hensel, 1867) at concentrations found in aquatic environments

Journal of Toxicology and Environmental Health, Год журнала: 2024, Номер 87(24), С. 1015 - 1029

Опубликована: Сен. 28, 2024

Anthranilic diamides (AD) are a modern class of insecticides used as alternatives to pyrethroids and neonicotinoids, particularly against lepidopteran pests. Despite their widespread use presence in surface waters, little is known regarding effects on amphibians. The aim this study was examine the environmentally-relevant concentrations AD chlorantraniliprole (CHLO) cyantraniliprole (CYAN) metamorphosis toad

Язык: Английский

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Design, Synthesis, and Insecticidal Evaluation of N-Pyridylpyrazole Amide Derivatives Containing 4,5-Dihydroisoxazole Amide as Potential Ryanodine Receptor Activators

Journal of Agricultural and Food Chemistry, Год журнала: 2023, Номер 71(37), С. 13688 - 13695

Опубликована: Сен. 6, 2023

Using the 4,5-dihydroisoxazol amide structure to expand aliphatic moiety of chlorantraniliprole, a series 28 novel N-pyridylpyrazolecarboxamide derivatives containing fragment were designed and synthesized. All target compounds had been properly characterized confirmed by 1H NMR, 13C HRMS, effects evaluated against Mythimna separata (M. separata) Plutella xylostella (P. xylostella). The bioassay results indicated that most exhibited good insecticidal activities M. P. at 50 mg/L; especially, compound A4 showed an LC50 value 3.27 mg/L separata. Calcium imaging experiments similar mechanism action causing increase in cytoplasmic Ca2+ concentration. molecular docking revealed possible binding mode with ryanodine receptor.

Язык: Английский

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Discovery of Novel Diamides Scaffold Containing Monofluoro-acrylamides Activating the Insect Ryanodine Receptor

Journal of Agricultural and Food Chemistry, Год журнала: 2023, Номер 71(39), С. 14137 - 14150

Опубликована: Сен. 21, 2023

The research and development of organofluorine chemistry has flourished; in particular, monofluoroalkene aroused considerable interest from medicinal organic chemists. It is a significant attempt to introduce into agrochemicals. In this study, was introduced diamide molecules inserted between the aliphatic amide benzene ring, 44 compounds have been successfully synthesized. bioassay results showed that with monofluoro-acrylamide moiety (Z-isomers) had excellent larvicidal activity against lepidopteran pests at 5 mg·L-1. LC50 values B16, B18, B21 Mythimna separata were 1.02, 1.32, 0.78 mg·L-1, respectively. 3D-QSAR analysis including CoMFA model CoMSIA conducted illustrate contributions steric, electrostatic, hydrophobic, hydrogen bond fields on bioactivity. Moreover, typical symptoms caused by chlorantraniliprole dehydration, shrinkage, blackening also observed test larvae treated compounds. M. central neurons calcium imaging experiment compound B18 indicated potential insect ryanodine receptor activators. molecular docking performed CHL binding domain Plutella xylostella RyR revealed predicted mode slightly different CHL. MM|GBSA dG Bind P. respectively -85.797 -95.641 kcal·mol-1. present work explored insecticidal properties new scaffold containing fragment extended application agrochemical field.

Язык: Английский

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3D-QSAR Combination with Molecular Dynamics Simulations to Effectively Design the Active Ryanodine Receptor Agonists against Spodoptera frugiperda

Journal of Agricultural and Food Chemistry, Год журнала: 2023, Номер 71(44), С. 16504 - 16520

Опубликована: Окт. 30, 2023

Computer-aided molecular modeling was applied to design a series of Spodoptera frugiperda RyR agonists. Comparative field analysis (CoMFA) and comparative similarity indices (CoMSIA) were used generate 3D-QSAR models. MD simulations in the complex with S. native, mutant RyR, mammalian RyR1 under physiological conditions validate detailed binding mechanism. Binding free energy calculation by mechanics generalized surface area (MM-GBSA) explained role key amino acid residues ligand–receptor binding. Therefore, 14 new compounds effectively designed synthesized, bioassay indicated that A-2 A-3 showed comparable activity chloranthraniliprole LC50 values 0.27, 0.18, 0.20 mg L–1, respectively, against frugiperda. Most target also displayed good Mythinma separata at 0.1 L–1. Molecular docking MM-GBSA calculations demonstrated had better capacity native RyRs.

Язык: Английский

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Theoretical insights into Rh-catalyzed hydroamidation: Mechanism and chemoselectivity

Molecular Catalysis, Год журнала: 2024, Номер 558, С. 114043 - 114043

Опубликована: Март 16, 2024

Язык: Английский

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