Synthesis and Fungicidal Activity of Novel Chloro-Containing 1-Aryl-3-oxypyrazoles with an Oximino Ester or Oximino Amide Moiety

Liu, Yuanyuan; Li, Yang; Chen, Nanqing; Lv, Kunzhi; Zhou, Chao; Xiong, Xingchuang; Fang-shi, LI

doi:10.3390/molecules19068140

Cited by 10 publications

(15 citation statements)

References 16 publications

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“…Intermediates N -arylpyrazoles I were synthesized from arylhydrazines via addition-cyclization and oxidation, which could then afford 4-bromo- N -arylpyrazoles IV by bromination 17 . Intermediate benzyl bromide ( E )-methyl 2-(2-(bromomethyl)phenyl)-2-(methoxyimino)acetate II was prepared from 1-( o -tolyl)ethanone via four steps including oxidation, esterification, oximation and bromination 8 . A previous report by Kim et al .…”

Section: Resultsmentioning

confidence: 99%

“…In our previous studies, several strobilurin analogues ( 4a-4f , 5a-5h , 6a-6h , Fig. 1 ) have been prepared by the substitution of N -arylpyrazoles with benzyl bromide in acetone, using potassium carbonate (K 2 CO 3 ) as acid-binding agent 7 , 8 . Motivated by this reaction, in our procedure, N -arylpyrazoles IV and I were allowed to react with benzyl bromide II and III , respectively, in a molar 1:1.1 equiv.…”

Section: Resultsmentioning

confidence: 99%

“…In our previous work, the methoxyiminoacetate pharmacophore of trifloxystrobin was introduced into the arylpyrazole structure, and a series of strobilurin analogues 4a-4f , 5a-5h , 6a-6h and 7a-7f were synthesized (Fig. 1 ) 6 – 8 . However, their fungicidal activity and structure-activity relationships (SARs) have not been discussed together in detail.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, fungicidal activity, structure-activity relationships (SARs) and density functional theory (DFT) studies of novel strobilurin analogues containing arylpyrazole rings

Liu

et al. 2018

Sci Rep

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A series of novel strobilurin analogues (1a-1f, 2a-2e, 3a-3e) containing arylpyrazole rings were synthesized and characterized by NMR spectroscopy. The structures of 1f, 2b and 3b were also determined by single crystal X-ray diffraction analysis. These analogues were collected together with other twenty-eight similar compounds 4a-4f, 5a-5h, 6a-6h and 7a-7f from our previous studies, for in vitro bioassays and thorough structure-activity relationships (SARs) studies. Most compounds exhibited excellent-to-good fungicidal activity against Rhizoctonia solani, especially 5c, 7a, 6c, and 3b with 98.94%, 83.40%, 71.40% and 65.87% inhibition rates at 0.1 μg mL−1, respectively, better than commercial pyraclostrobin. Comparative molecular field analysis (CoMFA) was employed to study three-dimensional quantitative structure-activity relationships (3D-QSARs). Density functional theory (DFT) calculation was also carried out to provide more information regarding SARs. The present work provided some hints for developing novel strobilurin fungicides.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, fungicidal activity, structure-activity relationships (SARs) and density functional theory (DFT) studies of novel strobilurin analogues containing arylpyrazole rings

Liu

et al. 2018

Sci Rep

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“…These compounds were screened for their antifungal and antibacterial activity as well and found almost equipotent to that of standard [42]. Liu et al [43] synthesized novel chloro containing 1-aryl-3oxypyrazoles derivatives and confirmed them with various spectroscopic techniques. They also screened these compounds against Rhizoctonia solani and found these compounds to be active.…”

Section: Number Of Leavesmentioning

confidence: 99%

Growth and Acclimatization Response of Sunflower Plantlets Treated with Naphthyl Acetic Acid-Based Environment Friendly Plant Growth Promoters

Sabir

Bareen

Rehman

et al. 2019

Pol. J. Environ. Stud.

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Although the development of organic products have been a decisive factor in rapid development for the last two centuries, hazardous solvents, nonbiodegradable catalysts, and long reaction times have always been a serious issue in organic synthesis. The solution to all issues highlighted above lies in the environment-friendly synthesis and green chemistry. In such synthesis, reaction time is decreased by using energy-efficient methods of heating (like microwave irradiation), high yield, biodegradability, good selectivity of solvents, good performance of catalysts, and usage of environment-friendly greener solvents like water, ethanol, acetone, etc. in an all-in-one approach [1]. Auxins, a class of naturally organic compounds, are plant growth hormones found in and required by plants in very little amounts, yet their presence is very critical. This class of compounds contain acetic acid-based Pol. AbstractPreparing novel compounds using environment-friendly protocols for plant growth has remained a major goal for plant scientists. In this research, effect of a novel plant growth promoter on sunflower (Helianthus annuus L.) was assessed hydroponically as well as in soil acclimatized plantlets at 1, 10, and 100 µM. The plants were also assessed for antioxidant enzymatic and antifungal activities. The synthesized derivative 2 produced significantly better results in terms of overall growth as compared with standards at 1 µM concentration among all compounds. Increased catalase and superoxide dismutase levels in plant seedlings treated with synthesized compounds were observed when grown in hydroponics, but these values were found to be significantly low as compared to soil-acclimatized plants. No significant zone of inhibition was found on agar plates in antifungal bioassay.

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“…The pyrazolones, an important class of heterocyclic compounds, are prevalent in a wide range of bioactive compounds with pharmaceutical and agricultural activities. [1][2][3][4][5] 4-Iodopyrazole-3-ols could open the way to a quick access to many pyrazolone analogues. However, iodination is usually difficult owing to the low electrophilicity of iodide.…”

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confidence: 99%

A Convenient One-Pot Synthesis of 1-Aryl-Substituted 4-Iodopyrazol-3-Ols via Aromatisation and Oxidative Iodination Reactions

Liu

Yang

Dong

et al. 2018

Journal of Chemical Research

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A convenient and economical one-pot synthesis of a series of new 1-aryl-substituted 4-iodopyrazole-3-ols from easily available pyrazolidin-3-ones in the presence of sodium iodide, 30% solution of hydrogen peroxide and a catalytic amount of sulfuric acid in dichloromethane via aromatisation and oxidative iodination reactions are described. This protocol has the advantages of high atom economy, cost-effectiveness, short reaction time and environmental friendliness.

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Synthesis and Fungicidal Activity of Novel Chloro-Containing 1-Aryl-3-oxypyrazoles with an Oximino Ester or Oximino Amide Moiety

Cited by 10 publications

References 16 publications

Synthesis, fungicidal activity, structure-activity relationships (SARs) and density functional theory (DFT) studies of novel strobilurin analogues containing arylpyrazole rings

Synthesis, fungicidal activity, structure-activity relationships (SARs) and density functional theory (DFT) studies of novel strobilurin analogues containing arylpyrazole rings

Growth and Acclimatization Response of Sunflower Plantlets Treated with Naphthyl Acetic Acid-Based Environment Friendly Plant Growth Promoters

A Convenient One-Pot Synthesis of 1-Aryl-Substituted 4-Iodopyrazol-3-Ols via Aromatisation and Oxidative Iodination Reactions

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