Understanding the Effects of Ligand Configuration on Protoporphyrinogen IX Oxidase with Rationally Designed 3-(N-Phenyluracil)but-2-enoates

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(15), P. 8401 - 8414

Published: April 8, 2024

Protoporphyrinogen IX oxidase (PPO, EC 1.3.3.4) is a promising target for green herbicide discovery. However, the ligand configuration effects on PPO activity were still poorly understood. Herein, we designed 3-(N-phenyluracil)but-2-enoates using our previously developed active fragments exchange and link (AFEL) approach synthesized series of novel compounds with nanomolar ranges Nicotiana tabacum (NtPPO) inhibitory potency herbicidal potency. Our systematic structure–activity relationship investigations showed that E isomers displayed improved bioactivity than their corresponding Z isomers. Using molecular simulation studies, found relatively lower entropy change could sample more stable binding conformation to receptor density functional theory (DFT) calculations higher chemical reactivity electronic potential Compound E-Ic emerged as optimal compound Ki value 3.0 nM against NtPPO, exhibiting broader spectrum weed control saflufenacil at 37.5–75 g ai/ha also safe maize 75 ai/ha, which be considered lead further development.

Language: Английский

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Bioisosteric-Replacement-Driven Lead Optimization of Tyclopyrazoflor

Journal of Agricultural and Food Chemistry, Journal Year: 2022, Volume and Issue: 70(36), P. 11123 - 11137

Published: May 13, 2022

A heterocyclic replacement strategy has been applied attempting to further optimize the biological properties of new insecticide tyclopyrazoflor, a pyridinyl-pyrazole compound with excellent activity against sap-feeding insects recently discovered by Corteva. Our research program on this novel chemical class was targeted evaluate importance both pyridyl and pyrazole moieties activity, properties, structure-activity. Synthetic methodologies have developed delivering our designed target compounds in moderate good yields. In attempt rationalize differences tyclopyrazoflor analogues, potential surface analysis based density functional theory (DFT) calculation DFT-derived Multiwfn VMD model performed. Furthermore, SwissBioisostere online database as great source for inspiration bioisosteric replacements.

Language: Английский

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Scaffold-Hopping Approach To Identify New Chemotypes of Dimpropyridaz

Journal of Agricultural and Food Chemistry, Journal Year: 2022, Volume and Issue: 70(36), P. 11109 - 11122

Published: April 12, 2022

Dimpropyridaz is a pyrazole carboxamide insecticide with novel mode of action, currently under worldwide development by BASF, providing excellent activity against sucking pests. A series dimpropyridaz analogues were designed to investigate the impact bioisosteric heterocyclic replacements on biological and molecular properties. Focus was given prepare where 4-pyridazinyl moiety replaced 5-pyrimidinyl, 2-pyrimidinyl, 3-pyridazinyl, 2-pyrazinyl groups. Five different synthetic routes developed for preparation these analogues, delivering target compounds in moderate good yields. We explained some aspects observed structure-activity relationship density functional theory (DFT) calculation DFT-derived Multiwfn VMD program models. These findings provide first insights into important role chemical class mechanism action dimpropyridaz.

Language: Английский

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Synthesis, Insecticidal Activities, and 3D-QASR of N-Pyridylpyrazole Amide Derivatives Containing a Phthalimide as Potential Ryanodine Receptor Activators

Journal of Agricultural and Food Chemistry, Journal Year: 2022, Volume and Issue: 70(39), P. 12651 - 12662

Published: Sept. 22, 2022

To develop potent and environment-friendly insecticides, novel N-pyridylpyrazole amide derivatives containing a phthalimide were designed synthesized. The preliminary bioassay results showed that most of the target compounds exhibited good insecticidal activities. For oriental armyworm (Mythimna separata), E5, E29, E30, E33 displayed higher than 90% lethal rates at 25 mg L-1. In particular, compound 60% mortality lower concentration 6.25 Besides, also 30% rate 5 L-1 against diamondback moth (DBM) (Plutella xylostella). Molecular docking between active DBM ryanodine receptor (RyR), comparative molecular field analysis (CoMFA), density functional theory (DFT) calculations conducted discussed. Furthermore, according to vitro studies using calcium imaging technique, was lead targeting insect RyR.

Language: Английский

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Novel phytotoxic compounds from Streptomyces sp. Caat 7–52: a potential bioherbicide against Conyza canadensis

Pest Management Science, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 5, 2025

Abstract BACKGROUND The rise of herbicide‐resistant weeds like Conyza canadensis L. poses a challenge to modern agriculture, driving the need for eco‐friendly alternatives. Microbial metabolites from actinobacteria species offer promising weed‐control solutions. This study aims screen and identify an isolate Brazil's Caatinga biome that produces phytotoxic characterize its compounds. RESULTS An isolate, named as Caat 7–52, was selected because significant effects against Lemna minor Phylogenetic analyses using six concatenated genes ( gyrB , recA rpoB trpB atpD 16S rRNA ) confirmed 7–52's close relationship Streptomyces musisoli TBRC 9950 T despite phenotypical differences. Bioassay‐directed isolation revealed 3‐hydroxybenzoic acid albocycline phytotoxins, with minimum inhibitory concentrations 50.00 3.12 μg mL −1 respectively. Albocycline analogues were also detected exhibited moderate phytotoxicity in . In addition, effectively inhibited seed germination C. concentration 6.25 marking first report albocycline's activity. Direct use fermented broth selectively dicot weeds, offering sustainable solvent‐free weed management strategy. CONCLUSION discovery sp. 7–52 metabolites, combined direct application broth, represents advancement control. bioherbicidal approach offers environmentally friendly alternative managing resistant supports broader microbial integrated pest programs. © 2025 Society Chemical Industry.

Language: Английский

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Design, Synthesis, and Antifungal activity of N'-Phenylnicotinohydrazide Derivatives as Promising Fungicide Candidates against Phytopathogenic Fungi

Journal of Molecular Structure, Journal Year: 2025, Volume and Issue: unknown, P. 141982 - 141982

Published: March 1, 2025

Language: Английский

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Rational Design and Synthesis of Isoxazoline Derivatives with Low Bee-Toxicity Based on Bee GABA Receptors

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 13, 2025

The isoxazoline insecticide, such as fluralaner, exhibits strong insecticidal activity against pests while showing no cross-resistance. However, due to its toxicity bees, the use of Fluralaner is restricted in veterinary antiparasitic applications. Hence, how modify structure fluralaner maintain and reduce bees vital meaningful. In this study, a virtual screening 11 diamide substructures was conducted based on GABA receptor (Apis mellifera), four compounds with lower docking scores were regarded potential low bee compounds. Among them, compound Y11 containing thiophene diamine motif used lead compound. Subsequently, A1-A16 B1-B11 synthesized Y11. Interestingly, A13 exhibited LC50 values 1.4 μg/mL diamondback moth (Plutella xylostella), outperforming commercial insecticide ethiprole (LC50 = 2.9 μg/mL). Furthermore, 9.9 fall armyworm (Spodoptera frugiperda), also Fipronil 78.8 Compound B1 12.4 corn borer (Pyrausta nubilalis), which surpassed that (30.8 Although P. xylostella S. frugiperda not potent Fluralaner, only 1/200 Fluralaner. Molecular dynamics studies elucidated interaction mode bee. has serve candidate low-toxicity alternative offering valuable insights for future design insecticide.

Language: Английский

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An overview of the synthesis of biheterocyclic compounds featuring four-membered rings containing nitrogen, oxygen, or sulfur

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134679 - 134679

Published: April 1, 2025

Language: Английский

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Substituted pyrazole derivatives as potential fungicidal agents

Phytochemistry Letters, Journal Year: 2024, Volume and Issue: 59, P. 117 - 123

Published: Jan. 19, 2024

Language: Английский

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Synthesis, crystal structure, Hirshfeld surface analysis, energy frameworks, molecular docking and DFT calculation of new pyrazole-4-carboxamide compound as antifungal agent

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1317, P. 139145 - 139145

Published: June 30, 2024

Language: Английский

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