Promising Fungicides from Allelochemicals: Synthesis of Umbelliferone Derivatives and Their Structure–Activity Relationships
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General Procedure for the Preparation of Compounds 2c–g
3.2. General Procedure for the Preparation of Compounds 3a–d and 4a–d
3.3. General Procedure for the Preparation of Compounds 5 and 6
3.4. General Procedure for the Preparation of Compound 7
3.5. General Procedure for the Preparation of Compound 8
3.6. General Procedure for the Preparation of Compounds 9 and 10
3.7. Antifungal Activity
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–10 are available from the authors. |
Compd. | The Inhibition Rate (%; mean ± SD; N = 3) | ||
---|---|---|---|
A. Alternata | B. Cinerea | F. Oxysporum | |
1 | 38.5 ± 4.38 | 25.8 ± 3.8 | 41.2 ± 2.5 |
2a | 38.1 ± 5.9 | 39.6 ± 6.2 | 33.2 ± 4.4 |
2b | 42.9 ± 6.7 | 36.3 ± 5.8 | 28.6 ± 3.4 |
2c | 70.6 ± 5.5 | 68.3 ± 4.6 | 60.4 ± 5.3 |
2d | 40.3 ± 3.7 | 46.2 ± 5.8 | 35.5 ± 7.2 |
2e | 63.7 ± 3.9 | 72.9 ± 3.5 | 62.8 ± 5.6 |
2f | 81.5 ± 3.7 | 90.99 ± 2.3 | 84.8 ± 3.2 |
2g | 48.4 ± 4.0 | 70.6 ± 5.2 | 53.5 ± 4.2 |
3a | 49.6 ± 3.6 | 41.2 ± 5.4 | 50.2 ± 6.3 |
3b | 3.8 ± 2.8 | 10.2 ± 2.6 | 8.4 ± 4.1 |
3c | 58.2 ± 3.6 | 63.0 ± 7.0 | 61.3 ± 3.8 |
3d | 29.6 ± 5.3 | 32.5 ± 6.2 | 26.2 ± 4.9 |
4a | 30.5 ± 5.2 | 32.1 ± 4.5 | 28.4 ± 5.8 |
4b | 35.3 ± 5.6 | 46.2 ± 3.7 | 33.2 ± 3.1 |
4c | 12.6 ± 2.6 | 15..0 ± 6.4 | 13.7 ± 4.2 |
4d | 10.2 ± 3.5 | 12.6 ± 4.5 | 9.8 ± 2.6 |
5 | 22.4 ± 4.7 | 26.4 ± 2.1 | 32.6 ± 5.6 |
6 | 27.6 ± 8.3 | 35.93 ± 1.73 | 29.8 ± 3.8 |
7 | 20.8 ± 7.7 | 21.9 ± 3.0 | 18.7 ± 4.1 |
8 | 26.6 ± 3.9 | 18.9 ± 8.5 | 25.3 ± 5.2 |
9 | 58.5 ± 3.4 | 70.9 ± 1.7 | 77.5 ± 3.4 |
10 | 77.3 ± 5.5 | 84.4 ± 3.5 | 80.5 ± 5.7 |
DMSO (1%) | 0 | 0 | 0 |
carbendazim | 90.7 ± 8.18 | 94.3 ± 6.4 | 91.4 ± 5.4 |
Compound | Log P | EC50 (95% CI μmol/L) | ||
---|---|---|---|---|
A. Alternata | B. Cinerea | F. Oxysporum | ||
1 | 1.61 | 922.4 (827.6–1098.9) | 1037.1 (955.3–1201.1) | 1165.9 (1076.2–1268.1) |
2c | 3.26 | 193.5 (145.6–258.7) | 221.1 (137.2–270.9) | 245.2 (180.9–298.2) |
2e | 2.62 | 381.6 (282.1–466.7) | 360.4 (274.1–462.7) | 405.9 (311.3–505.9) |
2f | 3.22 | 50.5 (28.5–82.2) | 30.7 (15.5–47.5) | 58.9 (30.4–89.3) |
2g | 3.11 | 232.1 (158.8–336.9) | 280.8(206.7–350.4) | 207.1 (149.8–279.2) |
9 | 2.87 | 185.8 (117.6–254.0) | 130.7 (76.0–195.7) | 182.9 (145.9–248.2) |
10 | 3.23 | 105.1 (69.5–176.2) | 66.6 (50.7–115.1) | 60.8 (34.6–120.6) |
Carbendazim | 1.29 | 18.8 (6.8–30.0) | 20.6 (7.8–32.4) | 33.5 (14.6–49.7) |
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Pan, L.; Lei, D.; Jin, L.; He, Y.; Yang, Q. Promising Fungicides from Allelochemicals: Synthesis of Umbelliferone Derivatives and Their Structure–Activity Relationships. Molecules 2018, 23, 3002. https://doi.org/10.3390/molecules23113002
Pan L, Lei D, Jin L, He Y, Yang Q. Promising Fungicides from Allelochemicals: Synthesis of Umbelliferone Derivatives and Their Structure–Activity Relationships. Molecules. 2018; 23(11):3002. https://doi.org/10.3390/molecules23113002
Chicago/Turabian StylePan, Le, Dongyu Lei, Lu Jin, Yuan He, and Qingqing Yang. 2018. "Promising Fungicides from Allelochemicals: Synthesis of Umbelliferone Derivatives and Their Structure–Activity Relationships" Molecules 23, no. 11: 3002. https://doi.org/10.3390/molecules23113002