Design, synthesis, herbicidal activity, and the molecular docking study of novel diphenyl ether derivatives as protoporphyrinogen IX oxidase inhibitors

Zhao, Li‐Xia; Peng, Juan; Hu, Jiajun; Zou, Yue-Li; Yin, Min-Lei; Wang, Zhixin; Gao, Shuang; Fu, Ying; Ye, Fei

doi:10.1016/j.molstruc.2022.132670

Cited by 5 publications

(3 citation statements)

References 44 publications

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“…Further analysis revealed that Compound 12a exhibited the highest herbicidal activity (100% inhibition rate) against Digitaria sanguinalis and Echinochloa crus-galli under soil treatment at a dose of 100 g/mu, and the control effect of Compound 12b under post-emergence was 100%. The phenoxypyridine could be linked with benzofuran via acylhydrazine to give aryloxyphenoxypropionic hydrazide derivatives and the herbicidal activity was tested by Yang et al [ 35 ]. At the dose of 75 g/hm 2 , Compound 13 showed greater than 90% inhibition against Beckmannia syzigachne (Steud.)…”

Section: Herbicides Containing Phenoxypyridine Scaffoldmentioning

confidence: 99%

Advancement of Phenoxypyridine as an Active Scaffold for Pesticides

Liu

Yong

et al. 2022

Molecules

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Phenoxypyridine, the bioisostere of diaryl ethers, has been widely introduced into bioactive molecules as an active scaffold, which has different properties from diaryl ethers. In this paper, the bioactivities, structure-activity relationships, and mechanism of compounds containing phenoxypyridine were summarized, which may help to explore the lead compounds and discover novel pesticides with potential bioactivities.

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Section: Herbicides Containing Phenoxypyridine Scaffoldmentioning

confidence: 99%

Advancement of Phenoxypyridine as an Active Scaffold for Pesticides

Liu

Yong

et al. 2022

Molecules

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“…It is the last isoenzyme in the synthesis of biological tetrahydropyrrole. It has been found in the inner mitochondrial membrane, chloroplast membrane, inner capsule, and protoplasm membrane. − When PPO is inhibited, protoporphyrinogen IX accumulates in large quantities and penetrates into the cytoplasm and is oxidized to produce a large amount of protoporphyrin IX. , Under the action of molecular oxygen, singlet oxygen is generated, resulting in the peroxidation and degradation of unsaturated fatty acids in the cell membrane, leading to plant cell death and ultimately plant death, which is manifested as leaf albino. , At present, the protoporphyrinogen oxidase inhibitor herbicides on the market are roughly divided into phenylpyrazole, triazolinone, diphenyl ether, oxadiazole, thiadiazole, pyrimidine dione, oxazolin dione, N -phenylphthalein imide, and others. − …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Activity Determination of Novel Phenylpyrazole Protoporphyrinogen Oxidase Inhibitor Herbicides Containing Five-Membered Heterocycles

Zhao,

Chen,

et al. 2023

J. Agric. Food Chem.

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Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) inhibitor herbicides have attracted widespread attention in recent years as ideal herbicides due to their high efficiency, low toxicity, and low pollution. In this article, 30 phenylpyrazole derivatives containing five-membered heterocycles were designed and synthesized according to the principle of bioelectronic isoarrangement and active substructure splicing. A series of structural characterizations were performed on the synthesized compounds. The herbicide activity in greenhouse was evaluated to determine their growth inhibition effect on weeds, their IC 50 value through in vitro PPO enzyme activity measurement was calculated, and target compounds 2i and 3j that have herbicide effects comparable to pyraflufen-ethyl were selected. Crop safety experiments have shown that when the spraying concentration is 300 g of ai/ha, gramineous crops such as wheat, corn, and rice are more tolerant to compound 2i, with wheat exhibiting high tolerance, which is equivalent to the crop safety of pyraflufen-ethyl. Compound 2i can be used as a candidate herbicide for wheat, corn, and paddy fields, and the results are consistent with the cumulative concentration experiment. Molecular docking results showed that compound 2i interacted with the amino acid residue ARG-98 by forming two hydrogen bonds and interacted with the amino acid residue PHE-392 by forming two π−π stacking interactions, indicating that compound 2i has more excellent herbicidal activity than pyraflufen-ethyl and is expected to become a potential lead compound of phenylpyrazole PPO inhibitor herbicides.

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“…According to the structural requirement of the exchangeable interlayer anion of LDHs [ 33 ], in this work, this phenolic acid derivative was converted into a series of longifolene-derived diphenyl ether carboxylic acid derivatives. It was used as the potentially exchangeable interlayer anion with biological activity in light of the good exhibition of diphenyl ether derivatives in the development of pesticides, which were employed as pesticides such as the herbicide Bifenox, the insecticide Pyriproxyfen and the fungicide Metominostrobin, and were continuously developed for crop protection [ 34 , 35 , 36 , 37 ]. All the target compounds were characterized and preliminarily evaluated for in vitro antifungal activities against eight fungi.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid Compounds

Lin

Duan

et al. 2023

Molecules

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Twenty-two novel longifolene-derived diphenyl ether-carboxylic acid compounds 7a–7v were synthesized from renewable biomass resources longifolene, and their structures were confirmed by FT-IR, 1H NMR, 13C NMR, and HRMS. The preliminary evaluation of in vitro antifungal activity displayed that compound 7b presented inhibition rates of 85.9%, 82.7%, 82.7%, and 81.4% against Alternaria solani, Cercospora arachidicola, Rhizoctonia solani, and Physalospora piricola, respectively, and compound 7l possessed inhibition rates of 80.7%, 80.4%, and 80.3% against R. solani, C. arachidicola, P. piricola, respectively, exhibiting excellent and broad-spectrum antifungal activities. Besides, compounds 7f and 7a showed significant antifungal activities with inhibition rates of 81.2% and 80.7% against A.solani, respectively. Meanwhile, a reasonable and effective 3D-QSAR mode (r2 = 0.996, q2 = 0.572) has been established by the CoMFA method. Furthermore, the drug-loading complexes 7b/MgAl-LDH were prepared and characterized. Their pH-responsive controlled-release behavior was investigated as well. As a result, complex 7b/MgAl-LDH-2 exhibited excellent controlled-releasing performance in the water/ethanol (10:1, v:v) and under a pH of 5.7.

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Design, synthesis, herbicidal activity, and the molecular docking study of novel diphenyl ether derivatives as protoporphyrinogen IX oxidase inhibitors

Cited by 5 publications

References 44 publications

Advancement of Phenoxypyridine as an Active Scaffold for Pesticides

Advancement of Phenoxypyridine as an Active Scaffold for Pesticides

Design, Synthesis, and Biological Activity Determination of Novel Phenylpyrazole Protoporphyrinogen Oxidase Inhibitor Herbicides Containing Five-Membered Heterocycles

Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid Compounds

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