Synthesis and Bioactivity Evaluation of Novel Thiochroman-4-One Derivatives Incorporating Carboxamide and 1, 3, 4-Thiadiazole Thioether Moieties

Yu, Lu; Xiao, Lingling; Li, Pei; Chi, Jiyan; Li, Jie; Tan, Shouyong

doi:10.1155/2022/5354088

Cited by 3 publications

(3 citation statements)

References 31 publications

(37 reference statements)

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“…As shown in Scheme 1 , using the botanical active components of carvacrol, thymol, guaiacol, and sesamol as the lead structures, intermediates 2 and 4 were prepared using the methods that have been previously reported ( Friedrich et al, 2020 ; Yu et al, 2022 ).…”

Section: Methodsmentioning

confidence: 99%

“…Meanwhile, the carboxamide and 1,3,4-thiadiazole thioether moieties had extensive pesticide biological activities, including antibacterial, antifungal, antiviral, and insecticidal activity ( Dalgaard, et al, 1994 ; Wu et al, 2016 ; Yang et al, 2018 ; Chen, et al, 2019 ; Yang et al, 2019 ; Tang et al, 2020 ; Chen et al, 2021 ). In our previous work, a series of novel thiochromanone derivatives containing carboxamide and 1,3,4-thiadiazole thioether moieties ( Figure 2 ) were prepared and demonstrated to have suitable antibacterial and antifungal activity ( Yu et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

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Novel botanical active component derivatives containing carboxamide and 1,3,4-Thiadiazole thioether moieties: Design, synthesis, and inhibitory activity

Chen

Zhu

et al. 2022

Front. Chem.

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In this study, using the botanical active components of carvacrol, thymol, guaiacol, and sesamol as the lead structures, 19 novel botanical active component derivatives containing carboxamide and 1,3,4-thiadiazole thioether moieties (5a−5s) were synthesized and structurally characterized by 1H NMR, 13C NMR, and HRMS. The antibacterial bioassay results in vitro showed that compound 2-(2-methoxyphenoxy)-N-(5-(methylthio)-1,3,4-thiadiazol-2-yl)acetamide (5k) revealed excellent inhibitory activities against Xanthomonas axonopodis pv. citri (Xac) and Xanthomonas oryzae pv. oryzicolaby (Xoc), with the median effective concentration (EC50) values of 22 and 15 μg/ml, respectively, which were even better than those of thiodiazole copper and bismerthiazol. Meanwhile, all the target compounds revealed lower in vitro inhibitory effects on Mucor bainieri (M. bainieri), Mucor fragilis (M. fragilis), and Trichoderma atroviride (T. atroviride), than carbendazim.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Novel botanical active component derivatives containing carboxamide and 1,3,4-Thiadiazole thioether moieties: Design, synthesis, and inhibitory activity

Chen

Zhu

et al. 2022

Front. Chem.

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“…and G. zeae by the growth rate method in comparison with albendazole at 50 μg/mL [18]. Each treatment was repeated 3 times.…”

Section: Preparation Procedures Of the Target Compounds E1-e15mentioning

confidence: 99%

Design, Synthesis, and Antifungal Activity of Novel Benzimidazole Derivatives Bearing Thioether and Carbamate Moieties

Lei

2022

Journal of Chemistry

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In this study, a series of benzimidazole derivatives bearing thioether and carbamate moieties have been synthesized and evaluated for their in vitro antifungal activity against Cytospora mandshurica, Thanatephorus cucumeris, Botrytis cinerea, Verticillium daliae, Phytophthora infestans, and Gibberella zeae by the mycelium growth rate method. The result of bioassay demonstrated that most of the compounds had certain antifungal activity. Especially, compound E11 revealed better antifungal activity against Verticillium daliae and Phytophthora infestans at 50 μg/mL, with the inhibition rates of 70% and 75%, respectively, than those of albendazole (38% and 61%, respectively). To the best of our knowledge, it is the first study on the synthesis and antifungal activity of benzimidazole derivatives containing thioether and carbamate moieties.

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Identification and Laboratory Fungicides Screening of the Pathogenic Fungus of Stem Spot of Pitaya (Hylocereus spp.) Stems

Luo

Guo

Shang

et al. 2022

Journal of Chemistry

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In this study, the pathogenic fungus of stem spot disease of pitaya (Hylocereus spp.) stems was identified by isolation and purification, pathogenicity test, morphological characteristics, and analysis of rDNA-ITS sequences. The results turned out that the rDNA-ITS sequences of the H1 strain showed 100% of identity with Botryosphaeria dothidea, indicating that the pathogenic fungus of stem spot disease of pitaya stems was Botryosphaeria dothidea. Meanwhile, the H1 strain was then used as a reference strain to screen some commercial fungicides. The bioassay test results indicated that prochloraz had an obvious inhibitory effect on Botryosphaeria dothidea with the EC50 value of 0.0798 μg/mL. Our study could provide a theoretical basis for the effective control method of stem spot disease of pitaya.

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Synthesis and Bioactivity Evaluation of Novel Thiochroman-4-One Derivatives Incorporating Carboxamide and 1, 3, 4-Thiadiazole Thioether Moieties

Cited by 3 publications

References 31 publications

Novel botanical active component derivatives containing carboxamide and 1,3,4-Thiadiazole thioether moieties: Design, synthesis, and inhibitory activity

Novel botanical active component derivatives containing carboxamide and 1,3,4-Thiadiazole thioether moieties: Design, synthesis, and inhibitory activity

Design, Synthesis, and Antifungal Activity of Novel Benzimidazole Derivatives Bearing Thioether and Carbamate Moieties

Identification and Laboratory Fungicides Screening of the Pathogenic Fungus of Stem Spot of Pitaya (Hylocereus spp.) Stems

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