Quinazoline-2,4-dione: A promising scaffold for herbicide discovery

Qu, Ren‐Yu; Nan, Jia-Xu; Yan, Yao-Chao; Lin, Hong‐Yan; Yang, Wen‐Chao; Yang, Guang‐Fu

doi:10.1016/b978-0-12-821035-2.00036-x

Cited by 2 publications

(1 citation statement)

References 17 publications

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“…After the discovery of the triketone-quinazoline-2,4-dione hybrid structure as a useful scaffold to find new HPPD inhibitors (details on the discovery and evolution of this scaffold in the field of herbicide agents was recently reviewed by Yang G.-F. and co-workers 27 ), a classical hit-to-lead optimization routine was applied by decoration of both the cyclohexyl ring, the quinazoline moiety, and the peripheral phenyl ring with halogens and small alkyl and alkoxy substituents. 28 As a result, in addition to benquitrione, another pivotal chemical entry (namely, the positional isomer of benquitrione, that is, the methyl-benquitrione or Y13287, Figure 10) was identified for its favorable weed control and crop safety comparable to those of both mesotrione and topramezone.…”

Section: ■ Decoration Of Minimum Common Pharmacophoric Motif To Overc...mentioning

confidence: 99%

Survey on the Recent Advances in 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Inhibition by Diketone and Triketone Derivatives and Congeneric Compounds: Structural Analysis of HPPD/Inhibitor Complexes and Structure–Activity Relationship Considerations

Governa

Bernardini

Braconi

et al. 2022

J. Agric. Food Chem.

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The serendipitous discovery of the HPPD inhibitors from allelopathic plants opened the way for searching new and effective herbicidal agents by application of classical hit-to-lead optimization approaches. A plethora of active and selective compounds were discovered that belong to three major classes of cyclohexane-based triketones, pyrazole-based diketones, and diketonitriles. In addition, to enhance inhibitory constant and herbicidal activity, many efforts were also made to gain broader weed control, crop safety, and eventual agricultural applicability. Moreover, HPPD inhibitors emerged as therapeutic agents for inherited and metabolic human diseases as well as vector-selective insecticides in the control of hematophagous arthropods. Given the large set of experimental data available, structure−activity relationship analysis could be used to derive suggestions for next generation optimized compounds.

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Section: ■ Decoration Of Minimum Common Pharmacophoric Motif To Overc...mentioning

confidence: 99%

Survey on the Recent Advances in 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Inhibition by Diketone and Triketone Derivatives and Congeneric Compounds: Structural Analysis of HPPD/Inhibitor Complexes and Structure–Activity Relationship Considerations

Governa

Bernardini

Braconi

et al. 2022

J. Agric. Food Chem.

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Prospects for the development of new herbicides based on natural compounds

Berestetskiy

2023

1727-1320

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Growing most major crops currently involves the use of chemical herbicides to control weeds. However, their regular use can lead to such undesirable consequences as contamination of soil and groundwater, accumulation of their residues in the crop, and the emergence of resistant populations of weeds. Therefore, developing of eco-friendly herbicides with new mechanisms of action is necessary. Natural phytotoxins of plant or microbial origin can serve as prototypes for active ingredients of chemical herbicides. This review considers: 1) the main modern trends in the development of chemical herbicides; 2) practical achievements in the use of natural compounds for weed control; 3) the use of phytotoxins as the basic components of synthetic herbicides. Analysis of the existing literature allowed us to identify some important approaches for the development of nature-derived herbicides: 1) the combination of virtual screening of libraries of natural compounds with high-throughput screening of selected substances in vitro and in vivo; 2) computer modelling and optimization of molecules using physico-chemical predictors and molecular docking; 3) development of new adjuvants and formulations, in particular on nanoscale, to reduce the application rates of active substances and the risks of their accumulation in the environment. The use of these approaches is likely to lead to the discovery of new promising herbicidal molecules for use in both organic and conventional agriculture.

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Quinazoline-2,4-dione: A promising scaffold for herbicide discovery

Cited by 2 publications

References 17 publications

Survey on the Recent Advances in 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Inhibition by Diketone and Triketone Derivatives and Congeneric Compounds: Structural Analysis of HPPD/Inhibitor Complexes and Structure–Activity Relationship Considerations

Survey on the Recent Advances in 4-Hydroxyphenylpyruvate Dioxygenase (HPPD) Inhibition by Diketone and Triketone Derivatives and Congeneric Compounds: Structural Analysis of HPPD/Inhibitor Complexes and Structure–Activity Relationship Considerations

Prospects for the development of new herbicides based on natural compounds

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