Discovery of novel benzoxazinone derivatives as promising protoporphyrinogen IX oxidase inhibitors

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

Published: May 9, 2025

Abstract BACKGROUND Protoporphyrinogen IX oxidase (PPO, EC 1.3.3.4) has emerged as a key target for developing new herbicides to protect crops from weeds. Herein, we disclose the development of two types PPO inhibitors by modification benzoxazinone skeleton. RESULTS Two structurally novel derivatives containing hydantoin or 1,2,3‐triazole fragments were designed based on active substructure splicing and derivatization strategies. Systematic post‐emergence herbicidal activity studies crop selectivity assessments indicate that some compounds exhibit excellent safety. For instance, compound A1 shows highly effective against all tested weeds at dosage 150 g ai/ha. Particularly, its broadleaf is comparable flumioxazin. Meanwhile, exhibits superior safety wheat maize compared flumioxazin within 75–150 ai/ha range. Molecular docking revealed occupy same cave Nicotiana tabacum ( Nt PPO). It noteworthy carbonyl group oxazolone moiety both forms beneficial interactions with Arg‐98 Phe‐392. CONCLUSION Our research indicates either serve promising chemical scaffold PPO‐inhibiting herbicides. © 2025 Society Chemical Industry.

Language: Английский

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Application of Asymmetric Catalysis in Chiral Pesticide Active Molecule Synthesis

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(31), P. 17153 - 17165

Published: July 25, 2024

The different configurations of chiral pesticides generally have significant influence on their biological activities. Chiral agrochemicals with high optical purities become a prominent topic in the research field new due to advantages including lower toxicity, higher efficiency, and reduced residue levels. However, most commercially available that possess elements are still used racemic forms. To date, asymmetric catalysis has emerged as versatile tool for enantioselective synthesis various novel pesticide active molecules. This perspective provides comprehensive overview applications diverse catalytic approaches facile preparation numerous molecules, our own outlook future development this highly direction is also presented at end review.

Language: Английский

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Regio- and Enantioselective N-Heterocyclic Carbene-Catalyzed Annulation of Aminoindoles Initiated by Friedel–Crafts Alkylation

Organic Letters, Journal Year: 2024, Volume and Issue: 26(33), P. 6993 - 6998

Published: Aug. 8, 2024

Chiral indoles annulated on the benzene ring are unique and significant in natural medicinal compounds. However, accessing these enantioenriched molecules has often been overlooked. The present study introduces an organocatalytic protocol to access compounds efficiently, demonstrated by substrate scope, functional group tolerance, using only 1 mol % of a chiral conjugated acid catalyst. Additionally, explores regioselectivity, gram-scale reactions, follow-up transformations, underscoring method's potential.

Language: Английский

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Carbene-Catalyzed Alkylation of Indoles

Synfacts, Journal Year: 2024, Volume and Issue: 20(05), P. 0538 - 0538

Published: April 15, 2024

Language: Английский

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Strategies Employing Transition‐Metal Free Conditions for C−C Bond Formation in Indoles

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(36)

Published: Sept. 19, 2024

Abstract Indole motifs are omnipresent in nature and can be found many natural products as well pharmaceuticals. It is for this reason synthetic transformations of indole have become a topic interest the organic medicinal chemist community decades. In review, we emphasized functionalization indoles via transition‐metal‐free approaches. This review touches on aspects different sub‐sections, which gives proposition tactics employed an overview road ahead.

Language: Английский

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