Synthesis of a New Group of Aliphatic Hydrazide Derivatives and the Correlations between Their Molecular Structure and Biological Activity
Abstract
:1. Introduction
2. Results and Discussion
No | Molecular Formula | Yield [%] | Composition [%] calculated | Composition [%] found | Formula Weight | Molar Volume | m.p. °C |
---|---|---|---|---|---|---|---|
1 | C9H9F3N2O2S | 86 | C (40.60) H (3.41) N (10.52) | C (40.5) H (3.42) | 266.24 | 176.2 ± 3.0 cm3 | 115–117 |
2 | C9H12N2O2S | 73 | C (50.92) H (5.70) N (13.20) | N (13.15) | 212.26 | 159.8 ± 3.0 cm3 | 171–173 |
3 | C14H11N3O2S | 97 | C (58.93) H (3.89) N (14.73) | -- | 285.32 | 191.1 ± 5.0 cm3 | 175 |
4 | C13H11N3O4S | 84 | C (51.14) H (3.63) N (13.76) | C (51.1) H (3.61) | 305.30 | 193.6 ± 3.0 cm3 | 166–167 |
5 | C13H10F2N2O2S | 79 | C (52.70) H (3.40) N (9.45) | N (9.48) | 296.29 | 190.2 ± 3.0 cm3 | 187–189 |
6 | C17H20N2O2S | 77 | C (64.53) H (6.37) N (8.85) | C (64.45) H (6.32) N(10.03) | 316.41 | 248.5 ± 3.0 cm3 | 104–107 |
7 | C15H16N2O2S | 75 | C (62.48) H (5.59) N (9.71) | N (9.68) | 288.36 | 214.3 ± 3.0 cm3 | 121–124 |
8 | C14H13ClN2O2S | 84 | C (54.46) H (4.24) N (9.07) | -- | 308.78 | 210.0 ± 3.0 cm3 | 110–112 |
9 | C13H12N2O2S | 98 | C (59.98) H (4.65) N (10.76) | -- | 260.31 | 181.8 ± 3.0 cm3 | 137–139 |
10 | C13H11FN2O2S | 82 | C (56.10) H (3.98) N (10.07) | C (56.15) H (4.0) N (10.03) | 278.30 | 186.0 ± 3.0 cm3 | 141–142 |
No | Structure | Log kw | S |
---|---|---|---|
1 | 3.05 | 3.17 | |
2 | 2.13 | 3.88 | |
3 | 3.56 | 3.98 | |
4 | 2.57 | 3.68 | |
5 | 3.05 | 3.09 | |
6 | 3.78 | 4.54 | |
7 | 3.05 | 3.78 | |
8 | 2.39 | 3.61 | |
9 | 2.22 | 3.91 | |
10 | 3.47 | 4.02 |
Compound number | Fusarium solani | Fusarium oxysporum | ||
---|---|---|---|---|
200 μg/mL | 100 μg/mL | 50 μg/mL | 200 μg/mL | |
1 | 3 | 3 | 3 | 3 |
2 | 3 | 2 | 1 | 1 |
3 | 3 | 3 | 2 | 3 |
4 | 3 | 3 | 1 | 1 |
5 | 3 | 2 | 2 | 3 |
6 | 3 | 3 | 3 | 3 |
7 | 3 | 3 | 2 | 3 |
8 | 3 | 3 | 2 | 1 |
9 | 2 | 1 | 0 | 1 |
10 | 3 | 3 | 3 | 1 |
Azoxystrobin | 3 | 3 | 3 | 3 |
Compound number | Aspergillus fumigatus | |||
---|---|---|---|---|
200 μg/mL | 100 μg/mL | 50 μg/mL | 25 μg/mL | |
1 | 3 | 3 | 2 | 2 |
2 | 3 | 3 | 3 | 3 |
3 | 2 | 2 | 2 | 0 |
4 | 2 | 1 | 1 | 0 |
5 | 3 | 1 | 1 | 1 |
6 | 3 | 3 | 3 | 3 |
7 | 3 | 2 | 2 | 2 |
8 | 2 | 2 | 0 | 0 |
9 | 1 | 1 | 0 | 0 |
10 | 3 | 3 | 3 | 3 |
Azoxystrobin | 3 | 3 | 2 | 2 |
3. Experimental
3.1. General
3.2. Synthesis
3.3. Chromatography (HPLC)
3.4. Biological Assays
Effective inhibition of linear growth in % | Evaluation of fungicidal activity | |
---|---|---|
Degree on scale | Activity | |
Above 80 | 3 | satisfactory |
50–79.9 | 2 | average |
20–49.9 | 1 | weak |
Below 20 | 0 | no activity |
4. Conclusions
Acknowledgements
- Samples Availability: Samples of the compound 4 are available from the authors.
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Kostecka, M. Synthesis of a New Group of Aliphatic Hydrazide Derivatives and the Correlations between Their Molecular Structure and Biological Activity. Molecules 2012, 17, 3560-3573. https://doi.org/10.3390/molecules17033560
Kostecka M. Synthesis of a New Group of Aliphatic Hydrazide Derivatives and the Correlations between Their Molecular Structure and Biological Activity. Molecules. 2012; 17(3):3560-3573. https://doi.org/10.3390/molecules17033560
Chicago/Turabian StyleKostecka, Małgorzata. 2012. "Synthesis of a New Group of Aliphatic Hydrazide Derivatives and the Correlations between Their Molecular Structure and Biological Activity" Molecules 17, no. 3: 3560-3573. https://doi.org/10.3390/molecules17033560