Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal Activities
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Acaricidal Activities
2.3. Herbicidal Activities
2.4. Antifungal Activities
3. Experimental Section
3.1. Chemistry
3.1.1. Synthesis of 1
3.1.2. Synthesis of 2a and 2b
3.1.3. Synthesis of 3a and 3b
3.1.4. General Procedure for Synthesis of 4-Methylumbelliferone Amide Derivatives (4aa–4ah, 4ba–4bq)
3.2. Procedures for ActivityEvaluation
3.2.1. Acaricidal Activity
3.2.2. Herbicidal Activity
3.2.3. Antifungal Activity
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Compd. | R | Compd. | R | Compd. | R |
---|---|---|---|---|---|
4aa | -CH2CH2CH3 | 4ba | -CH2CH2CH3 | 4bi | |
4ab | | 4bb | -CH(CH3)CH3 | 4bj | |
4ac | | 4bc | -CH2(CH2)9CH3 | 4bk | |
4ad | | 4bd | -CH2CH2CH2Cl | 4bl | |
4ae | | 4be | | 4bm | |
4af | | 4bf | | 4bn | |
4ag | | 4bg | | 4bo | |
4ah | | 4bh | | 4bp | |
4bq | |
Compd. | 200 mg/L | 1000 mg/L | Compd. | 200 mg/L | 1000 mg/L |
---|---|---|---|---|---|
4aa | 4.2 ± 5.2 | 12.9 ± 5.0 | 4bf | 18.4 ± 3.0 | 29.2 ± 6.3 |
4ab | 4.5 ± 3.2 | 27.1 ± 6.5 | 4bg | 40.3 ± 3.7 | 71.7 ± 5.4 |
4ac | 51.9 ± 9.9 | 88.3 ± 4.9 | 4bh | 54.0 ± 13.1 | 65.1 ± 6.6 |
4ad | 9.1 ± 5.0 | 19.4 ± 2.7 | 4bi | 87.8 ± 8.1 | 98.6 ± 6.1 |
4ae | 23.0 ± 4.9 | 42.1 ± 10.9 | 4bj | 26.6 ± 5.8 | 38.0 ± 8.0 |
4af | 33.9 ± 2.9 | 56.9 ± 4.7 | 4bk | 57.4 ± 10.9 | 79.8 ± 8.3 |
4ag | 32.8 ± 5.6 | 52.6 ± 7.3 | 4bl | 23.0 ± 6.3 | 31.7 ± 9.7 |
4ah | 30.0 ± 3.5 | 53.1 ± 7.5 | 4bm | 7.1 ± 8.6 | 55.0 ± 10.7 |
4ba | 20.4 ± 9.6 | 30.0 ± 3.4 | 4bn | 47.4 ± 10.3 | 58.8 ± 7.4 |
4bb | 11.8 ± 7.1 | 29.7 ± 10.0 | 4bo | 53.8 ± 8.0 | 63.4 ± 4.6 |
4bc | 61.5 ± 2.4 | 69.2 ± 2.4 | 4bp | 48.7 ± 9.5 | 62.6 ± 3.0 |
4bd | 75.1 ± 7.6 | 83.5 ± 5.6 | 4bq | 41.9 ± 3.0 | 72.6 ± 4.2 |
4be | 65.1 ± 3.2 | 73.8 ± 2.3 | Bifenazate | 93.5 ± 5.7 | 100.0 ± 0.0 |
Compd. | C. glaucum | Compd. | D. sanguinalis | Compd. | D. sanguinalis | |||
---|---|---|---|---|---|---|---|---|
Taproot | Caulis | Taproot | Caulis | Taproot | Caulis | |||
4af | 31.2 ± 9.7 | - | 4aa | 41.6 ± 2.6 | 67.4 ± 4.4 | 4bj | 10.6 ± 5.7 | 61.5 ± 12.4 |
4ah | - | 40.0 ± 5.3 | 4ab | 17.4 ± 7.4 | 33.6 ± 9.1 | 4bk | 41.9 ± 8.5 | 54.8 ± 8.7 |
4bb | 37.1 ± 9.6 | 16.8 ± 6.5 | 4ad | 25.5 ± 4.4 | 53.1 ± 8.9 | 4bl | 27.8 ± 5.2 | 48.5 ± 7.9 |
4bc | 40.1 ± 8.6 | 15.3 ± 6.5 | 4ag | 30.6 ± 3.6 | - | 4bm | 44.8 ± 7.7 | 12.2 ± 13.0 |
4be | 35.2 ± 3.4 | - | 4ba | 57.1 ± 4.3 | 70.1 ± 5.9 | 4bo | 64.6 ± 4.4 | 17.7 ± 5.1 |
4bf | 61.1 ± 9.7 | 50.6 ± 4.8 | 4bb | 66.7 ± 5.1 | 49.0 ± 12.8 | 4bp | 15.5 ± 3.3 | 42.5 ± 12.3 |
4bh | 76.3 ± 3.3 | 39.3 ± 1.9 | 4bc | - | 45.4 ± 11.7 | 4bq | 54.8 ± 4.3 | 60.9 ± 10.9 |
4bk | 41.8 ± 6.0 | - | 4bd | 3.4 ± 12.1 | 62.6 ± 10.4 | Acetochlor | 84.2 ± 7.0 | 78.1 ± 8.4 |
4bm | 51.1 ± 7.9 | - | 4be | 18.9 ± 6.8 | 40.5 ± 5.6 | |||
4bn | 31.1 ± 2.2 | 10.9 ± 8.1 | 4bf | 86.4 ± 10.6 | 71.8 ± 8.1 | |||
4bo | 30.1 ± 2.6 | 63.0 ± 5.8 | 4bg | 44.4 ± 11.7 | - | |||
4bq | 41.8 ± 6.0 | 9.4 ± 10.5 | 4bh | 96.2 ± 7.0 | 52.0 ± 6.4 | |||
Acetochlor | 88.2 ± 2.1 | 78.5 ± 7.0 | 4bi | 48.0 ± 6.7 | 47.7 ± 10.2 |
Compd. | F1 | Compd. | F2 | Compd. | F3 | Compd. | F4 | Compd. | F4 |
---|---|---|---|---|---|---|---|---|---|
4bf | 45.8± 8.6 | 4ab | 48.2± 7.4 | 4ac | 31.8± 7.9 | 4ab | 32.6± 1.1 | 4bj | 39.8± 2.1 |
4bh | 32.1±5.5 | 4ag | 45.9± 9.0 | 4bh | 38.4± 3.3 | 4ae | 32.6± 8.9 | 4bk | 88.7± 1.9 |
4bk | 56.6± 5.0 | 4bd | 54.6± 7.8 | 4bj | 36.1± 4.2 | 4ba | 47.3± 1.6 | 4bl | 48.1± 2.2 |
4bl | 39.3± 6.1 | 4be | 69.4± 6.2 | 4bk | 46.6± 1.9 | 4bd | 36.5± 1.6 | 4bm | 51.0± 2.5 |
4bq | 60.8± 3.6 | 4bf | 32.9± 9.8 | 4bn | 48.9± 4.1 | 4bf | 46.5± 4.0 | 4bn | 72.7± 4.1 |
Carb. | 88.9± 4.7 | 4bi | 57.8± 3.8 | 4bp | 47.9± 4.2 | 4bg | 66.1± 5.2 | 4bo | 34.8± 8.6 |
4bl | 34.5± 9.9 | 4bq | 71.2± 4.8 | 4bh | 84.9± 1.6 | 4bp | 81.8± 4.2 | ||
4bn | 37.7± 6.8 | Carb. | 70.9± 8.4 | 4bi | 58.4±2.7 | 4bq | 61.1± 4.8 | ||
Carb. | 54.1± 7.1 | Carb. | 76.1± 3.7 |
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Wei, Y.; Miao, K.-L.; Hao, S.-H. Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal Activities. Molecules 2018, 23, 122. https://doi.org/10.3390/molecules23010122
Wei Y, Miao K-L, Hao S-H. Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal Activities. Molecules. 2018; 23(1):122. https://doi.org/10.3390/molecules23010122
Chicago/Turabian StyleWei, Yan, Kai-Long Miao, and Shuang-Hong Hao. 2018. "Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal Activities" Molecules 23, no. 1: 122. https://doi.org/10.3390/molecules23010122