Citation: Wu Wenneng, Jiang Yangming, Zhang Buyan, Wang Jiazhong, Du Haitang, Fei Qiang. Syntheses and Fungicidal Activities of 1, 2, 4-Triazole Thioether Derivates Containing Acetamide Moiety[J]. Chemistry, ;2019, 82(12): 1115-1120. shu

Syntheses and Fungicidal Activities of 1, 2, 4-Triazole Thioether Derivates Containing Acetamide Moiety

1.
Food and Pharmaceutical Engineering Institute, Guiyang University, Guiyang 550005
2.
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550004
3.
China Tobacco Guizhou Industrial Co., Ltd., Guiyang 550025

Corresponding author: Fei Qiang, fqorganic@163.com
Received Date: 17 July 2019
Accepted Date: 23 July 2019

Figures(1)

1, 2, 4-triazole thioether acetamide derivatives 6a~6m were synthesized from 3, 4, 5-trimethoxy-benzoic acid through esterification, hydrazinolysis, cyclization, etherification, hydrolysis and condensation, and their structures were confirmed by ¹H NMR, ¹³C NMR, EMI-MS and elemental analysis. Preliminary bioactivity results indicated that compounds 6a~6m have a certain inhibitory on B. dothidea, Phomopsis sp. and B. cinerea in kiwi soft rot at the concentration of 50μg/mL. The Inhibition rate of compounds 6k and 6l against B. dothidea, Phomopsis sp. and B. cinerea were 83.4% to 91.3%. Meanwhile, the EC₅₀ value of compound 6k against B. dothidea and Phomopsis sp. were 46.6 μg/mL and 30.8 μg/mL, respectively, which were superior to that of the commercial agent pyrimethanil (57.6 μg/mL and 32.1 μg/mL). These results indicated that 1, 2, 4-triazole thioether acetamides have good fungicidal activities, and the results herein can provide reference for further development of highly active compounds.
- 1, 2, 4-Triazole,
- Amides,
- Synthesis,
- Fungicidal activity
1. [1]
  S M Madhu, U Nagarjuna, V Padmavathi et al. Eur. J. Med. Chem., 2018, 145: 1~10.
2. [2]
3. [3]
  R Jin, J Liu, G Zhang et al. Chem. Biodivers., 2018, 15(9): e1800263.
4. [4]
5. [5]
  Z W Zhai, Y X Shi, M Y Yang et al. Lett. Drug Des. Discov., 2016, 13: 521~525.
6. [6]
  H A El-Sayed, A H Moustafa, A E Z Haikal. Phosphorus Sulfur, 2013, 188(5): 649~662.
7. [7]
  D D Cheng, W Wei, Y Li et al. Chem. Res. Chin. Univ., 2017, 33(5): 758~764.
8. [8]
  S Maddila, R Pagadala, S B Jonnalagadda. J. Heterocycl. Chem., 2014, 52(2): 487~491.
9. [9]
  Y Zhang, B L Wang, Y Z Zhan et al. Chem. Res. Chin. Univ., 2016, 37(6): 1100~1107.
10. [10]
11. [11]
  W N Wu, M H Chen, R Wang et al. Chem. Papers, 2019, 73(3): 719~729.
12. [12]
  J X Chen, C F Yi, S B Wang et al. Bioorg. Med. Chem. Lett., 2019, 29(10): 1203~1210.
13. [13]
  K Gholivand, F Mohammadpanah, M Pooyan et al. Pestic. Biochem. Phys., 2019, 157: 122~137.
14. [14]
  J P K Gill, N Sethi, A Mohan. Orient. J. Chem., 2018, 34(5): 2378.
15. [15]
  F C Moraes, E S Alvarenga, K B Amorim et al. Pest Manag. Sci., 2015, 72(3): 580~584.
16. [16]
  X M Lan, D D Xie, L M Yin et al. Bioorg. Med. Chem. Lett., 2017, 27(18): 4270~4273.
17. [17]
  F Yang, C P He, P C Diao et al. Bioorg. Med. Chem. Lett., 2019, 29(1): 22~27.
18. [18]
19. [19]
1. [1]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
2. [2]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
3. [3]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
4. [4]
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5. [5]
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6. [6]
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8. [8]
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9. [9]
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10. [10]
  Peipei CUI , Yawen ZHENG , Pan LI , Peiyan GUAN , Zhaohong QIAN . Praseodymium-organic framework with 4, 4′-oxybis(benzoic acid): Rare broken layer structure, antibacterial activity, and sensing for Cd²⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1641-1649. doi: 10.11862/CJIC.20250152
11. [11]
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12. [12]
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13. [13]
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14. [14]
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15. [15]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
16. [16]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
17. [17]
  Xinghai Li , Zhisen Wu , Lijing Zhang , Shengyang Tao . Machine Learning Enables the Prediction of Amide Bond Synthesis Based on Small Datasets. Acta Physico-Chimica Sinica, 2025, 41(2): 2309041-0. doi: 10.3866/PKU.WHXB202309041
18. [18]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
19. [19]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
20. [20]
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沈阳化工大学材料科学与工程学院沈阳 110142