Microtubulin Assembly Inhibitors (Pyridines)

Lickfeldt, Darin W.; Cudworth, Denise P.; Loughner, Daniel D.; Markley, Lowell D.

doi:10.1002/9783527699261.ch10

Cited by 3 publications

(4 citation statements)

References 18 publications

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“…Thioester‐containing agrochemicals can be viewed as precursors of the corresponding carboxylic acids. Dithiopyr ( 117 ) is an herbicide inhibiting microtubulin assembly 82 . It is applied for pre‐ or post‐emergence control of annual grass and broad‐leaved weeds in turf.…”

Section: Thioestermentioning

confidence: 99%

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Sulfur‐based functional groups in agrochemistry

Jeanguenat

Lamberth

2023

Pest Management Science

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The element sulfur has an outstanding role in the crop protection chemistry because it is used in its elemental form as a multisite fungicide, but is also part of agrochemicals in the form of aromatic or aliphatic sulfur‐containing rings or sulfur‐based functional groups. This review gives an exhaustive overview over the latter category. Several fundamental agrochemical compound classes are named after a sulfur‐based functionality, such as the dithiocarbamate fungicides and sulfonylurea herbicides. Altogether, 16 different sulfur‐based functional groups are presented with their typical synthesis approaches and most important representatives in crop protection. © 2023 Society of Chemical Industry.

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Section: Thioestermentioning

confidence: 99%

“…Dithiopyr (117) is an herbicide inhibiting microtubulin assembly. 82 It is applied for pre-or post-emergence control of annual grass and broad-leaved weeds in turf. Dithiopyr is relatively immobile in the soil with a dissipation time (DT 50 ) of 8-150 days, depending on the soil composition.…”

Section: Thioestermentioning

confidence: 99%

Sulfur‐based functional groups in agrochemistry

Jeanguenat

Lamberth

2023

Pest Management Science

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“…inhibiting herbicide thiazopyr (8). 8,9 Also, the alanine moiety of the RNA polymerase inhibiting fungicide metalaxyl (9) can be exchanged by oxazolone, leading to oxadixyl (10) (Scheme 1). 10,11 Further heterocyles that are capable of mimicking carboxylic functions are pyridine (fenoxycarb → pyriproxyfen), 12 isoxazolidinone (fluralaner → isocycloseram), 13 oxazoline (diflubenzuron → etoxazole), 14 pyrazoline (diflubenzuron → PH60-40), 15 thiadiazole (chlorantraniliprole → JS9117), 16 and triazolone (trifloxystrobin → DPX-KZ165).…”

Section: Ring Closure By Replacement Of Carboxylic Functions With Cyc...mentioning

confidence: 99%

“…The exchange of one of the two different amide functions of the lead compound 1 by an isoxazoline led to a further 20-fold potency increase and the discovery of the oxysterol-binding protein inhibitor oxathiapiprolin ( 2 ), which is currently the most active commercialized fungicide against oomycetes diseases, such as potato late blight, caused by Phytophthora infestans, and grape downy mildew, caused by Plasmopara viticola. , The cyclization of N -methoxycarbamate toxophore of the complex III Qo site inhibitor pyraclostrobin ( 3 ) to N -methyltetrazolone delivered metyltetraprole ( 4 ). This new fungicide possesses high potency against Septoria tritici, a causal agent of wheat leaf blotch, in contrast to its lead compound pyraclostrobin also against the Qo-resistant Septoria mutation G143A. , The replacement of the methylester of the acetolactate synthase (ALS)-inhibiting herbicide halosulfuron ( 5 ) by dioxazine delivered metazosulfuron ( 6 ), an herbicide developed for the control of annual and perennial weeds in paddy field rice. , One of dithiopyr’s ( 7 ) two thioester functions is well-mimicked by a thiazoline ring, as demonstrated by the closely related microtubulin assembly inhibiting herbicide thiazopyr ( 8 ). , Also, the alanine moiety of the RNA polymerase inhibiting fungicide metalaxyl ( 9 ) can be exchanged by oxazolone, leading to oxadixyl ( 10 ) (Scheme ). , …”

Section: Ring Closure By Replacement Of Carboxylic Functions With Cyc...mentioning

confidence: 99%

Ring Closure and Ring Opening as Useful Scaffold Hopping Tools in Agrochemistry

Lamberth

2023

J. Agric. Food Chem.

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Ring closing acyclic parts of a molecular scaffold or the opposite manipulation, opening rings to produce pseudo-ring structures, is an important scaffold hopping manipulation. Analogues derived from biologically active compounds through the utilization of such strategies are often similar in shape and physicochemical properties and, therefore, likely to exhibit similar potency. This review will demonstrate how several different ring closure techniques, such as replacing carboxylic functions by cyclic peptide mimics, incorporating double bonds into aromatic rings, tying back ring substituents to a bicyclic structure, cyclizing adjacent ring substituents to an annulated ring, bridging annulated ring systems to tricyclic scaffolds, and exchanging gem-dimethyl groups by cycloalkyl rings, but also ring opening led to the discovery of highly active agrochemicals.

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Recent Advances in Organophosphorus‐Catalyzed Borylation and Silylation Reactions

2021

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Over the past few decades, organophosphorus catalysis has emerged as a robust platform for the preparation of highly functionalized molecules with excellent control of reactivity and selectivity. Organophosphorus catalysis has the advantages of mild and metal‐free reaction conditions. The easy‐to‐tune electronic and steric properties of phosphorus provide an easy handle for developing efficient synthetic methodologies with high stereochemical fidelity. This review describes the efforts to introduce boron and silicon functionalities into organic substrates catalyzed by organophosphorus compounds. These catalysts are categorized into nucleophilic, electrophilic, and biphilic phosphorus catalysts. Phosphorus compounds efficiently catalyze hydroboration of various unsaturated systems, carbonyl compounds, imines, etc.; hydro‐/cyano‐silylation of carbonyls; and silylation of alcohols. The present review emphasizes the scope of nucleophilic, electrophilic, and biphilic phosphorus‐based catalysis to introduce boron and silicon functionalities into organic compounds, mainly from the recent decade.

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Microtubulin Assembly Inhibitors (Pyridines)

Cited by 3 publications

References 18 publications

Sulfur‐based functional groups in agrochemistry

Sulfur‐based functional groups in agrochemistry

Ring Closure and Ring Opening as Useful Scaffold Hopping Tools in Agrochemistry

Recent Advances in Organophosphorus‐Catalyzed Borylation and Silylation Reactions

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