Design, microwave-assisted synthesis, bioactivity and SAR of novel substituted 2-phenyl-2-cyclohexanedione enol ester derivatives

Ye, Fei; Ma, Pengtao; Zhai, Yue; Yang, Fei; Gao, Shuang; Zhao, Li‐Xia; Fu, Ying

doi:10.1039/c8ra02647e

Cited by 15 publications

(10 citation statements)

References 30 publications

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“…Diclofop-methyl, developed by Farbwerke Hoechst Company, is designed by pharmacophore combination of phenoxycarboxylic acid and diphenyl ether herbicides [22]. As we noted above and continuous of our research on the design of nitrogen-containing heterocyclic safeners [23,24,25,26], a series of the new safener skeleton structure compounds are designed based on active substructure combinations retaining the trichloromethyl dichlorobenzene triazole of fenchlorazole and the nitrogen-containing heterocyclic ring of benoxacor or R-28725 as the parent skeleton structure (Scheme 2). Herein, we report the synthesis of a series of novel substituted trichloromethyl dichlorobenzene triazole compounds via cyclization and acylation without any expensive reagent or catalyst.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Evaluation of Novel Trichloromethyl Dichlorophenyl Triazole Derivatives as Potential Safener

et al. 2019

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The dominance of safener can unite with herbicides acquiring the efficient protection of crop and qualifying control of weeds in agricultural fields. In order to solve the crop toxicity problem and exploit the novel potential safener for fenoxaprop-P-ethyl herbicide, a series of trichloromethyl dichlorobenzene triazole derivatives were designed and synthesized by the principle of active subunit combination. A total of 21 novel substituted trichloromethyl dichlorobenzene triazole compounds were synthesized by substituted aminophenol and amino alcohol derivatives as the starting materials, using cyclization and acylation. All the compounds were unambiguously characterized by IR, 1H-NMR, 13C-NMR, and HRMS. A greenhouse bioassay indicated that most of the title compounds could protect wheat from injury caused by fenoxaprop-P-ethyl at varying degrees, in which compound 5o exhibited excellent safener activity at a concentration of 10 μmol/L and was superior to the commercialized compound fenchlorazole. A structure–activity relationship for the novel compounds was determined, which demonstrated that those compounds containing benzoxazine groups showed better activity than that of oxazole-substituted compounds. Introducing a benzoxazine fragment and electron-donating group to specific positions could improve or maintain the safener activity for wheat against attack by the herbicide fenoxaprop-P-ethyl. A molecular docking model suggested that a potential mechanism between 5o and fenoxaprop-P-ethyl is associated with the detoxication of the herbicide. Results from the present work revealed that compound 5o exhibited good crop safener activities toward wheat and could be a promising candidate structure for further research on wheat protection.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Evaluation of Novel Trichloromethyl Dichlorophenyl Triazole Derivatives as Potential Safener

et al. 2019

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“…It has been proposed that safeners can compete with herbicides for target sites of action, thereby reducing the concentration of herbicides reaching the target sites. − The best safety activity is exerted when the safener is structurally similar to the herbicide. , For instance, commercial safener fenchlorazole was found to exert its safety activity by binding to the herbicide target ACCase . Compound 1 is a diazabicyclo derivative structurally similar to commercial safener BAS-145138, which mitigated the NS toxicity to corn.…”

Section: Effects Of Safeners On Herbicide Target Sitesmentioning

confidence: 99%

Research Progress on the Action Mechanism of Herbicide Safeners: A Review

Zhao

2023

J. Agric. Food Chem.

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Herbicide safeners are agricultural chemicals that protect crops from herbicide injury and improve the safety of herbicides and the effectiveness of weed control. Safeners induce and enhance the tolerance of crops to herbicides through the synergism of multiple mechanisms. The principal mechanism is that the metabolic rate of the herbicide in the crop is accelerated by safeners, resulting in the damaging concentration at the site of action being reduced. We focused on discussing and summarizing the multiple mechanisms of safeners to protect crops in this review. It is also emphasized how safeners alleviate herbicide phytotoxicity to crops by regulating the detoxification process and conducting perspectives on future research on the action mechanism of safeners at the molecular level.

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“…On the basis of active substructure splicing and SARs, the active structures of the commercial herbicide safeners fenchlorazole-ethyl, isoxadifen-ethyl, furilazole, and mefenpyrdiethyl were spliced with the active fragment of the herbicide clethodim and substituted 2-phenyl-2-cyclohexanedione enol ester derivatives were designed by Ye and Fu's team (Scheme 25). 85 Good safener activity was exhibited by most of the target compounds. Fortunately, the highly active compound 23 showed encouraging safener activity in protecting maize from clethodim, comparable to the activity of the commercial safener cloquitocet-mexyl.…”

Section: ■ Introductionmentioning

confidence: 99%

Research Progress in the Design and Synthesis of Herbicide Safeners: A Review

Lee

Jin

Zhao

et al. 2022

J. Agric. Food Chem.

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Detoxification plays an important role in herbicide action. Herbicide safeners selectively protect crops from herbicide injury without reducing the herbicidal efficiency against the target weeds. With the large-scale use of herbicides, herbicide safeners have been widely used in sorghum, wheat, rice, corn, and other crops. In recent years, an increasing number of unexpected new herbicide safeners have been designed. The varieties, structural characteristics, uses, and synthetic routes of commercial herbicide safeners are reviewed in this paper. The design ideas and structural characteristics of novel herbicide safeners are summarized, which provide a basis for the design of bioactive molecules as new herbicide safeners in the future.

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Design, microwave-assisted synthesis, bioactivity and SAR of novel substituted 2-phenyl-2-cyclohexanedione enol ester derivatives

Abstract: Based on the structure–activity relationship and active substructure combination, a novel class of substituted 2-phenyl-2-cyclohexanedione enol ester derivatives was designed for use as potential herbicide safeners.

Cited by 15 publications

References 30 publications

Design, Synthesis and Evaluation of Novel Trichloromethyl Dichlorophenyl Triazole Derivatives as Potential Safener

Design, Synthesis and Evaluation of Novel Trichloromethyl Dichlorophenyl Triazole Derivatives as Potential Safener

Research Progress on the Action Mechanism of Herbicide Safeners: A Review

Research Progress in the Design and Synthesis of Herbicide Safeners: A Review

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