Dissipation of Herbicide Methiozolin and Its Metabolites in Aerobic Sediment–Water Systems

Kim, Jong-Hwan; Seo, Jong‐Su; An, Jin; Kwon, Young Chul; Hwang, Ki-Hwan; Koo, Suk-Jin; Kim, Jeong‐Han

doi:10.1007/s00128-020-02976-w

Cited by 3 publications

(1 citation statement)

References 32 publications

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“…At that time, the binding affinity to enzyme targets, e.g., acyl-ACP thioesterases, belonging to the protein family of FATs, was demonstrated by using co-crystallization, fluorescence-based thermal shift assays, and chemoproteomics techniques [3]. Likewise, methiozolin (2) is a recently assigned FAT inhibitor that has shown good results in selectively controlling grass weeds in both cool and warm seasons [7][8][9]. Recently, it has been shown that several herbicides bearing a gem-dimethylbenzylamide motif, e.g., cumyluron (3a) and oxaziclomefone (3b), previously exhibiting an unknown mode of action, control weeds due to the inhibition of FAT [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

Frackenpohl,

Barber,

Bojack

et al. 2024

Beilstein J. Org. Chem.

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The present work covers novel herbicidal lead structures that contain a 2,3-dihydro[1,3]thiazolo[4,5-b]pyridine scaffold as structural key feature carrying a substituted phenyl side chain. These new compounds show good acyl-ACP thioesterase inhibition in line with strong herbicidal activity against commercially important weeds in broadacre crops, e.g., wheat and corn. The desired substituted 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines were prepared via an optimized BH3-mediated reduction involving tris(pentafluorophenyl)borane as a strong Lewis acid. Remarkably, greenhouse trials showed that some of the target compounds outlined herein display promising control of grass weed species in preemergence application, combined with a dose response window that enables partial selectivity in certain crops.

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Section: Introductionmentioning

confidence: 99%

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

Frackenpohl,

Barber,

Bojack

et al. 2024

Beilstein J. Org. Chem.

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Discovery and optimization of spirocyclic lactams that inhibit acyl‐ACP thioesterase

Asmus,

Barber,

Bojack

et al. 2024

Pest Management Science

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BACKGROUNDThere are various methods to control weeds, that represent considerable challenges for farmers around the globe, although applying small molecular compounds is still the most effective and versatile technology to date. In the search for novel chemical entities with new modes of action that can control weeds displaying resistance we have investigated two spirocyclic classes of acyl‐ACP thioesterase inhibitors based on X‐ray co‐crystal structures and subsequent modelling studies.RESULTSBy exploiting scaffold hopping and isostere concepts we were able to identify new spirolactam‐based lead structures showing promising activity in vivo against commercially important grass weeds in line with strong target affinity.CONCLUSIONThe present work covers a series of novel herbicidal lead structures that contain a spirocyclic lactam as a structural key feature carrying ortho‐substituted benzyl or heteroarylmethylene side chains. These new compounds show good acyl‐ACP thioesterase inhibition in line with strong herbicidal activity. Greenhouse trials showed that the spirolactams outlined herein display promising control of grass‐weed species in pre‐emergence application combined with dose response windows that enable partial selectivity in wheat and corn. Remarkably, some of the novel acyl‐ACP thioesterase‐inhibitors showed efficacy against resistant grass weeds such as Alopecurus myosuroides and Lolium species on competitive levels compared with commercial standards.This article is protected by copyright. All rights reserved.

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Synthesis and biological profile of substituted hexahydrofuro[3,4‐b]furans, a novel class of bicyclic acyl‐acyl carrier protein (ACP) thioesterase inhibitors

Ahrens,

Barber,

Bojack

et al. 2024

Pest Management Science

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BACKGROUNDWeed control is a significant challenge for farmers around the globe. Of the various methods available for combatting weeds, small molecules remain the most effective and versatile technology to date. In the search for novel chemical entities with new modes of action toward herbicide‐resistant weeds, we have investigated hexahydrofuro[3,4‐b]furan‐based acyl‐acyl carrier protein (ACP) thioesterase inhibitors inspired by X‐ray co‐crystal structure‐based modeling studies.RESULTSBy exploiting scaffold hopping concepts and molecular modeling studies we were able to identify new hexahydrofuro[3,4‐b]furan‐based lead structures showing promising activity in vivo against commercially important grass weeds in line with strong target affinity.CONCLUSIONThe present work covers a series of novel herbicidal lead structures that possess a hexahydrofuro[3,4‐b]furan scaffold as a structural key feature, carrying ortho‐substituted aryloxy side chains. Based on an optimized synthetic approach a broad structure–activity relationship (SAR) study was carried out. The new compounds emerging from our modeling‐inspired structural variations show good acyl‐ACP thioesterase inhibition in line with promising initial herbicidal activity. Glasshouse trials showed that the hexahydrofuro[3,4‐b]furans outlined herein display good control of cold and warm season grass‐weed species in pre‐emergence application. Remarkably, some of the novel acyl‐ACP thioesterase‐inhibitors also showed promising efficacy against warm season weeds that are difficult to control. © 2024 The Author(s). Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

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Dissipation of Herbicide Methiozolin and Its Metabolites in Aerobic Sediment–Water Systems

Cited by 3 publications

References 32 publications

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

Discovery and optimization of spirocyclic lactams that inhibit acyl‐ACP thioesterase

Synthesis and biological profile of substituted hexahydrofuro[3,4‐b]furans, a novel class of bicyclic acyl‐acyl carrier protein (ACP) thioesterase inhibitors

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