Design, Synthesis, and Herbicidal Activity of Biaryl-Pyridazinone/Phthalimide Derivatives as Novel Protoporphyrinogen Oxidase Inhibitors

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

Published: March 6, 2025

In this study, a series of biaryl-pyridazinone/phthalimide derivatives were designed and synthesized as novel protoporphyrinogen IX oxidase (PPO) inhibitors. Herbicidal activity crop safety assessments revealed that some compounds exhibited excellent herbicidal profiles. For instance, at 37.5 g ai/ha, compound 7m inhibited Amaranthus retroflexus (AR), Abutilon theophrasti (AT), Medicago sativa (MS), Echinochloa crus-galli (EC), Digitaria sanguinalis (DS) with 90% to 100% efficacy, comparable the commercial herbicide saflufenacil (SAF). Compound still showed effective weed control against test broadleaf weeds lower dose 9.375 ai/ha. Additionally, demonstrated for wheat corn dosages up 150 vitro experiments representative significant inhibitory Arabidopsis thaliana PPO (AtPPO). Molecular docking Nicotiana tabacum (NtPPO) hydrogen bonding, π-π stacking, π-alkyl interactions between residues, such Cys-177, Thr-176, Arg-98, Phe-392, Leu-372. Furthermore, caused notable reduction in chlorophyll (Chl) content weeds. is promising candidate development herbicides.

Language: Английский

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Design, Synthesis, and Herbicidal Evaluation of Pyrrolidinone-Containing 2-Phenylpyridine Derivatives as Novel Protoporphyrinogen Oxidase Inhibitors

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(18), P. 10218 - 10226

Published: April 26, 2024

In this work, a series of pyrrolidinone-containing 2-phenylpyridine derivatives were synthesized and evaluated as novel protoporphyrinogen IX oxidase (PPO, EC 1.3.3.4) inhibitors for herbicide development. At 150 g ai/ha, compounds

Language: Английский

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Design, Synthesis, and Herbicidal Activities of N-(5-(3,5-Methoxyphenyl)-(thiazole-2-yl))phenoxyacetamide Derivatives

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(42), P. 23097 - 23107

Published: Aug. 13, 2024

Thiazole and phenoxyacetic acid are key moieties in many natural synthetic biologically active agents. A series of

Language: Английский

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Design, Synthesis, and Herbicidal Evaluation of Novel Synthetic Auxin Herbicides Containing 6-Indolylpyridine Oxime Ester/Amine

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

Published: Feb. 17, 2025

In this study, a series of 6-indolylpyridine oxime ester/amide derivatives were synthesized as novel synthetic auxin herbicides (SAHs) for postemergence herbicidal applications. At 30 g ai/ha, compounds 9q, 9u, 9v and 9w demonstrated inhibition rates 90 to 100% against weeds Echinochloa crus-galli (EC) Digitaria sanguinalis (DS). Even at reduced 7.5 these maintained over 90% four broadleaf weeds, with effects comparable those commercial halauxifen-methyl (HAM), indolauxipyr (IND) indolauxipyr-cyanomethyl (INC). Crop sensitivity tests confirmed the suitability 9u application in wheat rice fields ai/ha. Molecular docking analysis revealed that compound formed significant hydrogen bonding π–π stacking interactions key amino acid residues. Additionally, half maximal inhibitory concentration (IC50) values IAA vitro activity 6.153 4.389 μM, respectively, outperforming HAM (9.061 μM). Compounds show promising potential lead candidates SAHs.

Language: Английский

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Aminophosphonic Acid Derivatives 3r and 3s with Dual Herbicidal Activity and Crop Selectivity Targeted 5-Enolpyruvylshikimate-3-phosphate Synthase

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

Published: April 3, 2025

In this study, a series of aminophosphoric acid derivatives were synthesized with 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS) as potential target, and their herbicidal activities evaluated. At 600 g ai/ha, compounds 3r 3s exhibited good efficacy against Digitaria sanguinalis (DIGSA) Setaria viridis (SETVI), inhibition rates 80% 90%, 95%, respectively. Additionally, both demonstrated significant enzyme activity S. EPSPS (SvEPSPS). Expression purification SvEPSPS Portulaca oleracea (PoEPSPS) proteins followed by microscale thermophoresis (MST) revealed that had excellent binding affinities for PoEPSPS, dissociation constants (Kd) 0.65 1.27 μM, 0.41 0.42 Isothermal titration calorimetry (ITC) further validated the MST results, which consistent expectations. Molecular docking molecular dynamics (MD) simulations formed strong stable complexes PoEPSPS. Moreover, neither compound nor showed specific to SvEPSPSK355A PoEPSPSK355A mutant proteins, confirming K355 is key amino residue binding. These findings suggest have act selective inhibitors control six species grass weeds in crop fields.

Language: Английский

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Discovery of Novel (5-Mercapto-4-phenyl-4H-1,2,4-triazol-3-yl)methyl Phenyl Carbamate as a Potent Phytoene Desaturase Inhibitor through Scaffold Hopping and Linker Modification

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(34), P. 18898 - 18908

Published: Aug. 15, 2024

Phytoene desaturase (PDS) is a key rate-limiting enzyme in the carotenoid biosynthesis pathway. Although commercial PDS inhibitors have been developed for decades, it remains necessary to develop novel with higher bioactivity. In this work, we used scaffold hopping and linker modification approaches design synthesize series of compounds (

Language: Английский

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Pyridazine and pyridazinone compounds in crops protection: a review

Molecular Diversity, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

Language: Английский

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