Synthesis and Bioactivities of Novel 1‐(3‐Chloropyridin‐2‐yl)‐<i>N</i>‐Substituted‐5‐(Trifluoromethyl)‐Pyrazole Carboxamide Derivatives

Wu, Zhibing; Wu, Shian; Ye, Yiqiang; Zhou, Xiang; Wang, Peiyi; Xue, Wei; Hu, Deyu

doi:10.1002/jhet.2587

Cited by 13 publications

(8 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A compilation of structures of fluorinated pyrazoles, their activities, and the corresponding references during the last 5 years are provided in Figure . − …”

Section: Applications Of Fluorinated Pyrazolesmentioning

confidence: 99%

Fluorinated Pyrazoles: From Synthesis to Applications

2020

View full text Add to dashboard Cite

Fluorinated pyrazoles play an important role in medicinal chemistry, drug discovery, agrochemistry, coordination chemistry, and organometallic chemistry. Since the early 1990s, their popularity has grown exponentially. Moreover, more than 50% of all contributions on the topic have been published in the last 5 years. In this review, analysis of novel synthetic approaches to fluorinated pyrazoles that appeared in recent years is performed. A particular emphasis is devoted to a detailed consideration of reaction mechanisms. In addition, the reasons that have led to the ever-increasing popularity of fluorinated pyrazoles in various areas of science are discussed. At the end of the review, several potentially interesting but yet mostly unknown classes of fluorinated pyrazoles are outlined.

show abstract

“…A compilation of structures of fluorinated pyrazoles, their activities, and the corresponding references during the last 5 years are provided in Figure . − …”

Section: Applications Of Fluorinated Pyrazolesmentioning

confidence: 99%

Fluorinated Pyrazoles: From Synthesis to Applications

2020

View full text Add to dashboard Cite

show abstract

“…In our previous work , N ‐alkyl‐5‐trifluoromethyl pyrazole‐4‐carboxamide compounds exhibited certain bioactivities. To identify highly active compounds against phytopathogenic microbioorganisms, a series of N ‐phenyl and N ‐pyridinyl‐5‐trifluoromethyl pyrazole‐4‐carboxamide derivatives were designed and synthesized (Fig.…”

Section: Introductionmentioning

confidence: 96%

Design, Synthesis, Antifungal and Antibacterial Activities of N‐phenyl and N‐pyridinyl‐5‐(trifluoromethyl)‐pyrazole‐4‐carboxamide Derivatives

Yang

Zhou

2018

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

A series of N‐phenyl and N‐pyridinyl‐5‐(trifluoromethyl)‐pyrazole carboxamide derivatives (T1–T25) were designed and synthesized. Bioassay results indicated that antifungal and antibacterial activities of title compounds could be obviously improved by placing trifluoromethyl on the 5‐position of the pyrazole ring and substituted 4‐pyridinyl at the amine side of the amide bond. The EC50 values of T3 against Gibberella zeae, Cytospora mandshurica, and Fusarium oxysporum were 14.7, 21.1, and 32.7 μg/mL, respectively, better than hymexazol (30.2, 47.3, and 42.5 μg/mL) and carboxin (34.2, >200, and >200 μg/mL). And the EC50 values of T6, T11, T12, T15, T18, T19, T23, and T25 against rice bacterial leaf blight were 17.0, 21.8, 21.9, 18.6, 16.8, 25.9, 9.4, and 24.4 μg/mL, respectively, much better than bismerthiazol (70.5 μg/mL).

show abstract

“…Further analysis of the types of substitution positions on the pyrazole ring of the 12 commercial fungicides indicated that most types of substituted sites were 1,3-disubstituted or 1,3,5-trisubstituted on the pyrazole ring. − Furthermore, a series of novel pyrazole derivatives containing the active skeleton “5-trifluoromethyl-4-pyrazole carboxamide” were first reported in our previous work. Additional studies on the substituents at the 1-position of the pyrazole ring demonstrated that the substituents of the o -methylbenzene ring and o -trifluoromethyl benzene ring exhibited excellent antifungal activity, and mechanism studies revealed that all active compounds were potential SDHIs. − …”

Section: Introductionmentioning

confidence: 99%

Potential Fungicide Candidates: A Dual Action Mode Study of Novel Pyrazole-4-carboxamides against Gibberella zeae

Zhang

Yang

Zhao

et al. 2023

J. Agric. Food Chem.

Self Cite

View full text Add to dashboard Cite

Pyrazole carboxamides are a class of traditional succinate dehydrogenase inhibitors (SDHIs) that have developed into a variety of commercialized fungicides. In the present work, a series of novel 1,5-disubstituted-1H-pyrazole-4-carboxamide derivatives were designed and synthesized based on the active backbone of 5-trifluoromethyl-1H-4-pyrazole carboxamide. Bioassay results indicated that some target compounds exhibited excellent in vitro antifungal activities against six phytopathogenic fungi. Notably, the EC 50 values of Y 47 against Gibberella zeae, Nigrospora oryzae, Thanatephorus cucumeris, and Verticillium dahliae were 5.2, 9.2, 12.8, and 17.6 mg/L, respectively. The in vivo protective and curative activities of Y 47 at 100 mg/L against G. zeae on maize were 50.7 and 44.2%, respectively. Three-dimensional quantitative structure−activity relationship (3D-QSAR) analysis revealed that the large steric hindrance and electronegative groups on the 5-position of the pyrazole ring were important for the activity. The IC 50 value of Y 47 against succinate dehydrogenase (SDH) was 7.7 mg/L, superior to fluopyram (24.7 mg/L), which was consistent with the docking results. Morphological studies with fluorescence microscopy (FM) and scanning electron microscopy (SEM) found that Y 47 could affect the membrane integrity of mycelium by inducing endogenous reactive oxygen species (ROS) production and causing peroxidation of cellular lipids, which was further verified by the malondialdehyde (MDA) content. Antifungal mechanism analysis demonstrated that the target compound Y 47 not only had significant SDH inhibition activity but could also affect the membrane integrity of mycelium, exhibiting obvious dual action modes. This research provides a novel approach to the development of traditional SDHIs and their derivatives.

show abstract

Synthesis and Bioactivities of Novel 1‐(3‐Chloropyridin‐2‐yl)‐N‐Substituted‐5‐(Trifluoromethyl)‐Pyrazole Carboxamide Derivatives

Cited by 13 publications

References 15 publications

Fluorinated Pyrazoles: From Synthesis to Applications

Fluorinated Pyrazoles: From Synthesis to Applications

Design, Synthesis, Antifungal and Antibacterial Activities of N‐phenyl and N‐pyridinyl‐5‐(trifluoromethyl)‐pyrazole‐4‐carboxamide Derivatives

Potential Fungicide Candidates: A Dual Action Mode Study of Novel Pyrazole-4-carboxamides against Gibberella zeae

Contact Info

Product

Resources

About