Design, Synthesis, and Fungicidal Activity of α-Methylene-γ-Butyrolactone Derivatives Bearing a Diphenyl Ether Moiety DOI
Caiyun Chen, Hong‐Wei He, Dan Xu

и другие.

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 26, 2024

The γ-butyrolactone scaffold, commonly present in natural products and bioactive compounds, has played a crucial role the development of novel pesticides. In this study, series α-methylene-γ-butyrolactone derivatives containing diphenyl ether moiety were designed synthesized using scaffold splicing strategy. Bioassays revealed that several target compounds demonstrated potent fungicidal activities, particularly against Phytophthora capsici Valsa mali. Notably, compound B7 (EC50 = 0.809 mg/L) exhibited highest antioomycete activity P. capsici, outperforming famoxadone 41.0 but being less effective than dimethomorph 0.180 mg/L). Meanwhile, C22 1.47 showed strongest antifungal V. mali, which was higher those 1.80 13.6 vivo experiments confirmed satisfactory protective curative effects better famoxadone. Additionally, found to inhibit sporangia formation, zoospore release, cystospore germination at 10 mg/L. Physiological biochemical studies indicated can induce changes mycelial morphology increase cell membrane permeability, modulate respiratory metabolism. Furthermore, both vitro enzymatic inhibition assays molecular docking analysis suggested primary mechanism action may involve binding complex III on chain. This work provides valuable insights for incorporating as agricultural agents.

Язык: Английский

Synthesis and Herbicidal Activity of Di-substituted Pyrimidine-Biphenyls and Study of Molecular Mode of Action DOI

Yitao Yan,

Yinglu Chen,

Hanxian Hu

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(1), С. 358 - 358

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0
Scaffold hopping approaches for the exploration of herbicidally active compounds inhibiting Acyl‐ACP Thioesterase DOI Creative Commons
Tyler Fahrenhorst‐Jones, Stephanie Lee,

Birgit Bollenbach‐Wahl

и другие.

Pest Management Science, Год журнала: 2024, Номер unknown

Опубликована: Авг. 19, 2024

Abstract BACKGROUND The sustainable control of weed populations is a significant challenge facing farmers around the world. Although various methods for weeds exist, use small molecule herbicides remains most effective and versatile approach. Striving to find novel that combat resistant via targeting plant specific modes action (MoAs), we further investigated bicyclic class acyl‐acyl carrier protein (ACP) thioesterase (FAT) inhibitors in an effort safe efficacious lead candidates. RESULTS Utilizing scaffold hopping bioisosteric replacements strategies, explored new FAT. Amongst compounds identified structural motifs showed promising target affinity coupled with good vivo efficacy against commercially important species. We studied structure–activity relationship (SAR) dihydropyranopyridine which promise as type FAT inhibiting herbicides. CONCLUSION current work presents how approaches can be implemented successfully herbicidal structures optimized potential agricultural practices. were demonstrated have vitro inhibitory activity MoA well showing variety species, particularly grass greenhouse trials on levels competitive commercial standards. © 2024 Author(s). Pest Management Science published by John Wiley & Sons Ltd behalf Society Chemical Industry.

Язык: Английский

Процитировано

2
Investigation of acetyl‐CoA carboxylase‐inhibiting herbicides that exhibit soybean crop selectivity DOI Creative Commons
Stephanie J. Lee, China M. Payne, Shaun Rees

и другие.

Pest Management Science, Год журнала: 2024, Номер unknown

Опубликована: Окт. 12, 2024

Abstract The sustainable control of weed populations, particularly resistant species, is a significant challenge in agriculture around the world. α‐aryl‐keto‐enol (aryl‐KTE) class acetyl‐CoA carboxylase (ACCase)‐inhibiting herbicides represent possible solution for grasses even though achieving crop selectivity remains challenge. Herein, we present some our investigations into identifying most promising structural features within aryl‐KTE that give highest chance soybean selectivity, whilst also maintaining strong and broad efficacy against problematic species. We further examined results by preparing new molecules which were evaluated glasshouse screening assays their herbicidal as well selectivity. consider uniting this approach with other optimization criteria, such toxicological environmental safety profiles, will enable streamlining protection optimizations programmes, ultimately delivering safer more solutions to farmers consumers. © 2024 Author(s). Pest Management Science published John Wiley & Sons Ltd on behalf Society Chemical Industry.

Язык: Английский

Процитировано

2
Discovery and Mode-of-Action Characterization of a New Class of Acetolactate Synthase-Inhibiting Herbicides DOI
Hudson Kagueyama Takano, Zoltán Benkő, Moriah Zielinski

и другие.

Journal of Agricultural and Food Chemistry, Год журнала: 2023, Номер 71(47), С. 18227 - 18238

Опубликована: Авг. 11, 2023

Herbicides are effective tools to manage weeds and enable food production sustainable agriculture. Corteva Agriscience R&D has recently discovered new diphenyl-ether compounds displaying excellent postemergent efficacy on important weed species along with corn safety. Here, we describe the chemistry, biology, biochemistry, computational modeling research that led discovery elucidation of primary mode action for these compounds. The target protein was found be acetolactate synthase (ALS), a key enzyme in biosynthesis branched chain amino acids (valine, leucine, isoleucine). While resistance evolution ALS herbicides is widespread, molecular interaction at active site differs significantly from some commercial inhibitors. unique biochemical profile molecules their herbicidal activity selectivity make them noteworthy development pursuit novel, safe, control solutions.

Язык: Английский

Процитировано

6
Mining Medicinally Relevant Bioreduction Substrates Inspired by Ligand-Based Drug Design DOI Creative Commons
Alexander J. Rago, Ioanna Zoi, Jackson A. Gartman

и другие.

Опубликована: Май 13, 2024

Exploring the scope of biocatalytic transformations in absence enzyme structures without extensive experimentation is a challenging task. To expand limited substrate capacity carrot-mediated bioreduction and hunt for new medicinally relevant ketones with minimum cost labor time, we deployed practical method inspired by ligand-based drug design. Through analyzing collected literature data building pharmacophore reactivity prediction models, screened self-built virtual library >8000 bearing most frequently used N, O, S-heterocycles functional groups discovery. Representative examples were validated, expanding scope. The public availability our models alongside straightforward screening workflow make it time-, labor-, cost-saving to evaluate unknown substrates medicinal chemistry applications, especially large set structurally differentiated ketones. Our studies also showcase novelty utilizing principles solve general biocatalysis problem.

Язык: Английский

Процитировано

1
Discovery of a New Class of Lipophilic Pyrimidine-Biphenyl Herbicides Using an Integrated Experimental-Computational Approach DOI Creative Commons

Yitao Yan,

Yinglu Chen,

Hanxian Hu

и другие.

Molecules, Год журнала: 2024, Номер 29(11), С. 2409 - 2409

Опубликована: Май 21, 2024

Herbicides are useful tools for managing weeds and promoting food production sustainable agriculture. In this study, we report on the development of a novel class lipophilic pyrimidine-biphenyl (PMB) herbicides. Firstly, three PMBs, Ia, IIa, IIIa, were rationally designed via scaffold hopping strategy determined to inhibit acetohydroxyacid synthase (AHAS). Computational simulation was carried out investigate molecular basis efficiency PMBs against AHAS. With rational binding mode, highest in vitro as well vivo potency, Ia identified preferable hit. Furthermore, these integrated analyses guided design eighteen new which synthesized one-step Suzuki–Miyaura cross-coupling reaction. These Iba-ic, more effective post-emergence control grass compared with Ia. Interestingly, six displayed 98–100% inhibition at 750 g ai/ha. Remarkably, Ica exhibited ≥ 80% 187.5 Overall, our comprehensive systematic investigation revealed that structurally distinct PMB herbicides, pair excellent herbicidal activities interactions AHAS, represent noteworthy pursuit weed solutions.

Язык: Английский

Процитировано

1
Mining Medicinally Relevant Bioreduction Substrates Inspired by Ligand-Based Drug Design DOI
Alexander J. Rago, Ioanna Zoi, Jackson A. Gartman

и другие.

Journal of Medicinal Chemistry, Год журнала: 2024, Номер 67(15), С. 13174 - 13186

Опубликована: Июль 25, 2024

Exploring the scope of biocatalytic transformations in absence enzyme structures without extensive experimentation is a challenging task. To expand limited substrate capacity carrot-mediated bioreduction and hunt for new medicinally relevant ketones with minimum cost labor time, we deployed practical method inspired by ligand-based drug design. Through analyzing collected literature data building pharmacophore reactivity prediction models, screened self-built virtual library >8000 bearing most frequently used N,O,S-heterocycles functional groups discovery. Representative examples were validated, expanding scope. The public availability our models alongside straightforward screening workflow makes it time-, labor-, cost-saving to evaluate unknown substrates medicinal chemistry applications, especially large set structurally differentiated ketones. Our studies also showcase novelty utilizing principles solve general biocatalysis problem.

Язык: Английский

Процитировано

0
Polyfluorinated benzoic acids as promising reagents for organic synthesis and medicinal chemistry DOI
Evgeny V. Shchegolkov, Yanina V. Burgart,

Irina V. Shchur

и другие.

Russian Chemical Reviews, Год журнала: 2024, Номер 93(8), С. RCR5131 - RCR5131

Опубликована: Авг. 1, 2024

Polyfluoroaromatic compounds occupy a special place in organic synthesis due to wide range of their chemical transformations and unique biological properties. The introduction the carboxyl function into polyfluoroarenes allows further diversification chemistry these compounds. This review summarizes data on polyfluorobenzoic acids, including derivatives polyfluorosalicylic acids. reactions esterification, amidation, reduction, decarboxylation, metal-catalyzed decarboxylative cross-coupling, C–H functionalization, reductive defluorination, nucleophilic aromatic substitution, heterocyclization complex formation are considered. Reactivity features polyfluorobenzoates comparison non-fluorinated counterparts highlighted. potential for practical applications acid derivatives, primarily as biologically active compounds, is presented. <br> Bibliography includes 300 references.

Язык: Английский

Процитировано

0
Design, Synthesis, and Fungicidal Activity of α-Methylene-γ-Butyrolactone Derivatives Bearing a Diphenyl Ether Moiety DOI
Caiyun Chen, Hong‐Wei He, Dan Xu

и другие.

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 26, 2024

The γ-butyrolactone scaffold, commonly present in natural products and bioactive compounds, has played a crucial role the development of novel pesticides. In this study, series α-methylene-γ-butyrolactone derivatives containing diphenyl ether moiety were designed synthesized using scaffold splicing strategy. Bioassays revealed that several target compounds demonstrated potent fungicidal activities, particularly against Phytophthora capsici Valsa mali. Notably, compound B7 (EC50 = 0.809 mg/L) exhibited highest antioomycete activity P. capsici, outperforming famoxadone 41.0 but being less effective than dimethomorph 0.180 mg/L). Meanwhile, C22 1.47 showed strongest antifungal V. mali, which was higher those 1.80 13.6 vivo experiments confirmed satisfactory protective curative effects better famoxadone. Additionally, found to inhibit sporangia formation, zoospore release, cystospore germination at 10 mg/L. Physiological biochemical studies indicated can induce changes mycelial morphology increase cell membrane permeability, modulate respiratory metabolism. Furthermore, both vitro enzymatic inhibition assays molecular docking analysis suggested primary mechanism action may involve binding complex III on chain. This work provides valuable insights for incorporating as agricultural agents.

Язык: Английский

Процитировано

0