Synthesis and Antifungal Activity of Benzamidine Derivatives Carrying 1,2,3-Triazole Moieties
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
Compounds | Inhibition rate (%) | |||
---|---|---|---|---|
in vitro (200 μg/mL) | in vivo (300 μg/mL) | |||
C. lagenarium | B. cinerea | C. lagenarium | B. cinerea | |
4a | 26 | 23 | 49 | 19 |
4b | 19 | 14 | 30 | 60 |
4c | 17 | 25 | 60 | 23 |
4d | 8 | 0 | 0 | 16 |
4e | 10 | 12 | 48 | 56 |
9a | 32 | 22 | 57 | 24 |
9b | 31 | 30 | 79 | 49 |
9c | 61 | 17 | 4 | 13 |
9d | 29 | 44 | 17 | 35 |
9e | 35 | 14 | 45 | 14 |
15a | 12 | 16 | 31 | 43 |
15b | 25 | 19 | 61 | 68 |
15c | 12 | 24 | 0 | 48 |
15d | 10 | 13 | 0 | 46 |
16a | 25 | 15 | 19 | 11 |
16b | 16 | 8 | 56 | 32 |
16c | 10 | 5 | 52 | 47 |
16d | 26 | 13 | 90 | 7 |
17a | 65 | 36 | 52 | 74 |
17b | 21 | 19 | 27 | 0 |
17c | 32 | 12 | 45 | 45 |
17d | 10 | 17 | 53 | 31 |
Carbendazim | 100 | 100 | 85 | 61 |
2.2. Antifungal Activity Bioassay
3. Experimental
3.1. General Information
3.2. Synthesis of 4-(Azidomethyl)benzonitrile (2) [42]
3.3. Synthesis of 4-((4-(Hydroxymethyl)-1H-1,2,3-triazol-1-yl)methyl) Benzonitrile (3)
3.4. General Procedure for the Synthesis of 4-((4-(Hydroxymethyl)-1H-1,2,3-triazol-1-yl) Methyl)-benzamidines 4a–e
3.5. Synthesis of 1-Nitro-2-(prop-2-ynyloxy) Benzene (7)
3.6. Synthesis of 4-((4-((2-Nitrophenoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl) Benzonitrile (8)
3.7. General Procedure for the Synthesis of 4-((4-((2-Nitrophenoxy)methyl)-1H-1,2,3 -triazol-1-yl)-methyl)-benzamidines 9a–e
3.8. Synthesis of 1-Nitro-4-(prop-2-ynyloxy)benzene (12) [51]
3.9. Synthesis of 3-(Azidomethyl)benzonitrile (14)
3.10. General Procedure for the Synthesis of 3-(Azidomethyl)benzamidines 15a–d [42]
3.11. General Procedure for the Synthesis of 3-((4-(Hydroxymethyl)-1H-1,2,3-triazol-1-yl)methyl)-benzamidines 16a–d
3.12. General Procedure for the Synthesis of 3-((4-((4-Nitrophenoxy)methyl)-1H-1,2,3-triazol-1-yl) methyl)benzamidines 17a–d
3.13. Fungicidal Activity Bioassay: Effect of the New Compounds on the Mycelial Growth of C. lagenarium and B. cinerea in Solid Media
3.14. Effect on C. lagenarium and B. cinerea Activity on Cucumber Leaves [53]
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Chen, G.; Zhou, Y.; Cai, C.; Lu, J.; Zhang, X. Synthesis and Antifungal Activity of Benzamidine Derivatives Carrying 1,2,3-Triazole Moieties. Molecules 2014, 19, 5674-5691. https://doi.org/10.3390/molecules19055674
Chen G, Zhou Y, Cai C, Lu J, Zhang X. Synthesis and Antifungal Activity of Benzamidine Derivatives Carrying 1,2,3-Triazole Moieties. Molecules. 2014; 19(5):5674-5691. https://doi.org/10.3390/molecules19055674
Chicago/Turabian StyleChen, Guangyou, Yiwan Zhou, Chonglin Cai, Jia Lu, and Xing Zhang. 2014. "Synthesis and Antifungal Activity of Benzamidine Derivatives Carrying 1,2,3-Triazole Moieties" Molecules 19, no. 5: 5674-5691. https://doi.org/10.3390/molecules19055674