Synthesis and Fungicidal Evaluation of 2-Arylphenyl Ether-3-(1<i>H</i>-1,2,4-triazol-1-yl)propan-2-ol Derivatives

Yu, Guan‐Ping; Xu, Lingfei; Xu, Yangsheng; Bi, Wen-Zhao; Zhu, Qi; Zhai, Zhigang

doi:10.1021/jf900222s

Cited by 15 publications

(13 citation statements)

References 12 publications

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“…1,2,4-Triazole, an important class of heterocyclic rings, has attracted increasing attention due to their broad activities, such as fungicidal [1,2], insecticidal [3,4], herbicidal [5,6], and bactericidal [7,8]. It may also serve as a plant growth regulatory agent [9] and has excellent potential in the pesticide field.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety

Tang

Jin

Mou

et al. 2013

Chemistry Central Journal

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BackgroundPlant fungi (e.g., Pellicularia sasakii, Gibberella zeae, Fusarium oxysporum, and Cytospora mandshurica and Phytophthora infestans) and bacteria (e.g., Ralstonia solanacearum) are extremely difficult to manage in agricultural production. The high incidence of plant mortality and the lack of effective control methods make P. sasakii and R. solanacearum two of the world’s most destructive plant pathogens. Pathogenic fungi and bacteria are responsible for billions of dollars in economic losses worldwide each year. Thus, we designed an active amide structure and synthesized a series of novel amide derivatives containing a triazole moiety to discover new bioactive molecules and pesticides that can act against fungi and bacteria.ResultsA series of amide derivatives containing a triazole moiety were synthesized. All the obtained compounds were characterized through proton and carbon nuclear magnetic resonance spectroscopy, infrared spectroscopy, and elemental analysis. Preliminary antifungal activity test showed that some of the synthesized compounds exhibited moderate antifungal activity against P. sasakii, G. azeae, F. oxysporum, C. mandshurica, and P. infestans at 50 mg/L. Compound 4u displayed more potent antifungal activity against P. sasakii and G. azeae than hymexazol. Preliminary antibacterial activity results showed that some of the synthesized compounds exhibited high anti-bacterial activity against R. solanacearum at 200 mg/L. Compounds 4m and 4q displayed high antibacterial activity against R. solanacearum, with 71% and 65% inhibitory rates, respectively.ConclusionsA series of novel amide derivatives containing 1,2,4-triazole moiety were synthesized through the reaction of intermediate 3 with different acyl chlorides and anhydrous potassium carbonates in anhydrous tetrahydrofuran at 50°C, using 2,4-dichloroacetophenoneas as a starting material. The title compounds exhibited high inhibitory effects against P. sasakii, R. solanacearum, and G. azeae.

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Section: Introductionmentioning

confidence: 99%

Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety

Tang

Jin

Mou

et al. 2013

Chemistry Central Journal

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“…Experimental results revealed that the ratio of reactants, solvent, reaction time, amount of catalyst as well as the addition rate of concentration sulfuric acid exerted important influences on the yield of hydroxytriazole (2). Therefore, we optimized the cyclization conditions, and exploited an one-pot, three-component synthesis strategy to construct the 1,2,4-triazole ring, which represented an easy, convenient and efficient synthetic route.…”

Section: Resultsmentioning

confidence: 99%

“…[2][3][4][5][6][7][8][9] Noticeably, 1,2,4-triazoles as antimicrobial agents have aroused special attention in medicinal chemistry in recent years due to their prominent activity, low toxicity as well as broad spectrum. 10 So far a large number of 1,2,4-triazole antimicrobial compounds have been extensively used in clinic.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Halobenzyloxy and Alkoxy 1,2,4-Triazoles and Evaluation for Their Antifungal and Antibacterial Activities

Wan¹,

Zhou

2010

Bulletin of the Korean Chemical Society

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A new class of halobenzyloxy or alkoxy 1,2,4-triazoles and their hydrochlorides were synthesized through cyclization starting from commercially available phenylhydrazine. The structures were characterized by MS, IR and 1 H NMR spectra as well as elemental analyses. All the synthesized compounds were screened for their antibacterial activities in vitro against Staphylococcus aureus (ATCC29213), methicillin-resistant Staphylococcus aureus (N315), Bacillus subtilis, Escherichia coli (ATCC25922), Pseudomonas aeruginosa, Shigella dysenteriae, Eberthella typhosa, and antifungal activities against Candida albicans (ATCC76615), Aspergillus fumigatus by broth microdilution assay method. The results of preliminary bioassay indicated that 3-(2,4-difluorobenzyloxy)-1-phenyl-1H-1,2,4-triazole hydrochloride exhibited the best inhibitory activity with an MIC value of 56.25 µM against P. aeruginosa superior to Chloramphenicol, and showed comparable activity with Chloramphenicol against E. coli (ATCC25922).

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“…Recently, interest in fluorine-containing compounds is continuously growing since fluorinated organic products exhibit unique properties that areofgreat interest foravariety of applications [2,3]. The title compound has been obtained during asearch for new fuorine-containing compounds with better biological activity.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2,2-dibromo-1-(4-fluoro-2-(4-fluorophenoxy)phenyl) ethanone, C14H8Br2F2O2

Shen

Zhai

2014

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThem ixture of sodium p-fluorophenol( 1.34 g, 10 mmol), 2,4-difluoroacetophenone (1.56g ,1 0m mol), copper(II)chloride (0.02 g) and toluene (10 mL)was stirred at reflux 2h,and then concentrated under vacuum.After cooling to room temperature, hexamethylene(20 mL)was addedtothe residue, whereafter the organiclayer waswashedwithbrine (5 mL)three times. Subsequently, bromine (3.20 g, 20 mmol) in hexamethylene (5 mL) was added dropwise to the above mentioned solution and stirred for 2ha tr oom temperature, and washed with saturated sodium bisulfite solution (5 mL). The title compound was obtained in 75% yield when the organic layer was washed with water to neutral, dried over MgSO4,stripped under the condition of reduced pressure. Single crystals suitable for X-ray measurements were obtained by slow evaporationofits ethanolsolution at room temperature. ExperimentaldetailsAllh ydrogena toms were positioned geometricallya nd refined using ariding model, with C-H =0.93 or 0.98 Åand with U iso (H) =1.2 times U eq (C). DiscussionRecently, interest in fluorine-containing compounds is continuously growing since fluorinated organic products exhibit unique properties that areofgreat interest foravariety of applications [2,3]. The title compound has been obtained during asearch for new fuorine-containing compounds with better biological activity. In the title structure, all bond lengths are normal [4] and in agood agreement with those reported previously [5][6]. Thea tom F1, O2, C7, C9 and the phenyl ring (C1-C6) arecoplanar. The dihedral angle between the phenyl rings is 73.22°. The bond angle of C2-O2-C9 is 121

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Synthesis and Fungicidal Evaluation of 2-Arylphenyl Ether-3-(1H-1,2,4-triazol-1-yl)propan-2-ol Derivatives

Cited by 15 publications

References 12 publications

Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety

Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety

Synthesis of Novel Halobenzyloxy and Alkoxy 1,2,4-Triazoles and Evaluation for Their Antifungal and Antibacterial Activities

Crystal structure of 2,2-dibromo-1-(4-fluoro-2-(4-fluorophenoxy)phenyl) ethanone, C14H8Br2F2O2

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