4-Disubstituted Pyrazolin-3-Ones—Novel Class of Fungicides against Phytopathogenic Fungi
Abstract
:1. Introduction
2. Results and Discussion
2.1. The Synthesis of the 4,4-Disubstituted Pyrazolone Derivatives
2.2. Study of the Fungicidal Activity of 4,4-Disubstituted Pyrazolones
3. Materials and Methods
3.1. 4-Hydroxy-4,5-dimethyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 1b [57]
3.2. 4-Methoxy-4,5-dimethyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 1c
3.3. 4-Fluoro-4,5-dimethyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 1d
3.4. 4-Chloro-4,5-dimethyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 1e [58]
3.5. 4-Bromo-4,5-dimethyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 1f [58]
3.6. 4,4-Difluoro-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 2d [59]
3.7. 4,4-Dichloro-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 2e [60]
3.8. 4,4-Dibromo-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 2f [61]
3.9. 4-Azido-4,5-dimethyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 1g
3.10. 4,4-Diazido-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one 2g [54]
3.11. 4,5-Dimethyl-2-phenyl-4-thiocyanato-2,4-dihydro-3H-pyrazol-3-one 1h [55]
3.12. 4,4’,5,5’-Tetramethyl-2,2’-diphenyl-2,2’,4,4’-tetrahydro-3H,3’H-[4,4’-bipyrazole]-3,3’-dione, meso 1i and racemic 1j [62]
3.13. Investigation of Fungicidal Activity (Table 1)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compound | C, mg/L | Mycelium Growth Inhibition | ||||||
---|---|---|---|---|---|---|---|---|
V. i. | R. s. | F. o. | F. m. | B. s. | S. s. | |||
1 | 10 | 100 | 100 | 61 | 100 | 100 | 88 | |
2 | 10 | 7 | 20 | 11 | 8 | 0 | 0 | |
3 | 10 | 11 | 25 | 6 | 17 | 1 | 14 | |
4 | 10 | 58 | 51 | 80 | 89 | 74 | 42 | |
5 | 10 | 100 | 100 | 55 | 61 | 66 | 36 | |
6 | 10 | 100 | 100 | 31 | 83 | 60 | 54 | |
7 | 10 | 29 | 32 | 53 | 68 | 53 | 36 | |
8 | 10 | 100 | 100 | 85 | 100 | 77 | 100 | |
5 | 100 | 100 | 68 | 100 | 52 | 31 | ||
9 | 10 | 100 | 100 | 100 | 100 | 100 | 100 | |
5 | 100 | 100 | 97 | 100 | 62 | 100 | ||
10 | 10 | 33 | 38 | 8 | 22 | 6 | 1 | |
11 | 10 | 100 | 100 | 50 | 83 | 74 | 28 | |
12 | 10 | 22 | 39 | 11 | 11 | 16 | 11 | |
13 | 10 | 11 | 26 | 17 | 11 | 12 | 0 | |
14 | 10 | 11 | 24 | 6 | 19 | 14 | 0 | |
15 | Kresoxim-methyl | 10 | 100 | 100 | 65 | 64 | 58 | 54 |
16 | Triadimefon | 10 | 49 | 58 | 62 | 82 | 64 | 63 |
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Lopat’eva, E.R.; Budnikov, A.S.; Krylov, I.B.; Alekseenko, A.L.; Ilovaisky, A.I.; Glinushkin, A.P.; Terent’ev, A.O. 4-Disubstituted Pyrazolin-3-Ones—Novel Class of Fungicides against Phytopathogenic Fungi. Agrochemicals 2023, 2, 34-46. https://doi.org/10.3390/agrochemicals2010004
Lopat’eva ER, Budnikov AS, Krylov IB, Alekseenko AL, Ilovaisky AI, Glinushkin AP, Terent’ev AO. 4-Disubstituted Pyrazolin-3-Ones—Novel Class of Fungicides against Phytopathogenic Fungi. Agrochemicals. 2023; 2(1):34-46. https://doi.org/10.3390/agrochemicals2010004
Chicago/Turabian StyleLopat’eva, Elena R., Alexander S. Budnikov, Igor B. Krylov, Anna L. Alekseenko, Alexey I. Ilovaisky, Alexey P. Glinushkin, and Alexander O. Terent’ev. 2023. "4-Disubstituted Pyrazolin-3-Ones—Novel Class of Fungicides against Phytopathogenic Fungi" Agrochemicals 2, no. 1: 34-46. https://doi.org/10.3390/agrochemicals2010004