Design, Synthesis, and Acaricidal Activity of 2,5-Diphenyl-1,3-oxazoline Compounds
Abstract
:1. Introduction
2. Result and Discussion
2.1. Synthesis
2.2. Acaricidal Activity
3. Materials and Methods
3.1. Preparation of Test Compounds
3.1.1. (4-Vinylphenyl)methanol (2)
3.1.2. 2-Bromo-1-(4-(hydroxymethyl)phenyl)ethan-1-ol (3)
3.1.3. 2-(2-Hydroxy-2-(4-(hydroxymethyl)phenyl)ethyl)isoindoline-1,3-dione (4)
3.1.4. 2-(2-((tert-Butyldimethylsilyl)oxy)-2-(4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)ethyl)isoindoline-1,3-dione (5)
3.1.5. 2-((tert-Butyldimethylsilyl)oxy)-2-(4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)ethan-1-amine (6)
3.1.6. N-(2-((tert-Butyldimethylsilyl)oxy)-2-(4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)ethyl)-2,6-difluorobenzamide (7)
3.1.7. 2,6-Difluoro-N-(2-hydroxy-2-(4-(hydroxymethyl)phenyl)ethyl)benzamide (8)
3.1.8. N-(2-Chloro-2-(4-(chloromethyl)phenyl)ethyl)-2,6-difluorobenzamide (9)
3.1.9. 5-(4-(Chloromethyl)phenyl)-2-(2,6-difluorophenyl)-4,5-dihydrooxazole (10)
3.1.10. Preparation of Target Compound 2-(4-(2-(2,6-difluorophenyl)-4,5-dihydrooxazol-5-yl)benzyl)isoindoline-1,3-dione (11a)
3.1.11. Preparation of Target Compounds 11b–11g and 11t–11x
3.1.12. Preparation of Target Compounds 11h–11m
3.1.13. Preparation of Target Compounds 11n–11s
3.1.14. Preparation of Target Compound 11y
3.2. Acaricidal Activity Evaluation
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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Mortality (%) against Eggs | Mortality (%) against Larvae | |||||
---|---|---|---|---|---|---|
Compound | 100 mg/L | 10 mg/L | 5 mg/L | 100 mg/L | 10 mg/L | 5 mg/L |
11a | 100 | 68.7±9.8 | 0 | 100 | 61.7 ± 12.8 | 33.7 ± 10.2 |
11b | 100 | 20.0 ± 2.2 | - | 100 | 54.3 ± 7.2 | 31.0 ± 6.2 |
11c | 100 | 76.8 ± 4.9 | 14.3 ± 3.4 | 100 | 78.4 ± 6.0 | 55.4 ± 2.6 |
11d | 100 | 91.5 ± 2.9 | 6.6 ± 2.5 | 68.4 ± 7.3 | 30.4 ± 9.4 | - |
11e | 100 | 86.8 ± 6.5 | 0 | 61.7 ± 12.2 | 23.7 ± 1.8 | - |
11f | 100 | 28.6 ± 13 | - | 100 | 54.7 ± 5.0 | 26.7 ± 5.7 |
11g | 100 | 20.4 ± 0.3 | - | 100 | 78.3 ± 18.2 | 42.5 ± 15.7 |
11i | 100 | 49.5 ± 0.7 | - | 100 | 72.0 ± 3.6 | 41.4 ± 9.7 |
11j | 100 | 0.0 | - | 100 | 83.1 ± 9.2 | 59.7 ± 15.7 |
11k | 100 | 49.6 ± 3.5 | - | 100 | 74.2 ± 7.4 | 52.0 ± 2.0 |
11l | 100 | 100 | 15.3 ± 5.0 | 100 | 52.3 ± 3.4 | 38.6 ± 9.2 |
11n | 100 | 20 ± 0.5 | - | 100 | 63.0 ± 8.3 | 47.0 ± 1.5 |
11o | 100 | 100 | 16.3 ± 5.3 | 100 | 61.1 ± 12.1 | 44.1 ± 23.3 |
11p | 0 | 0 | - | 91.8 ± 6.8 | 36.8 ± 3.5 | - |
11q | 100 | 100 | 22.3 ± 11.6 | 100 | 56.6 ± 7.7 | 42.6 ± 6.9 |
11r | 100 | 50 ± 4.2 | - | 78.5 ± 2.0 | 36.4 ± 10.2 | - |
11s | 0 | 0 | - | 73.2 ± 1.8 | 44.8 ± 10.6 | - |
11t | 100 | 100 | 0 | 88.2 ± 6.8 | 54.7 ± 5.0 | 20.6 ± 5.4 |
11u | 100 | 90.6 ± 8.3 | 0 | 94.2 ± 5.5 | 52.9 ± 9.0 | 36.7 ± 2.3 |
11v | 100 | 59.0 ± 0.9 | 0 | 91.6 ± 8.4 | 36.2 ± 2.1 | - |
11w | 0 | 0 | - | 83.7 ± 1.8 | 39.4 ± 6.1 | - |
11x | 91.4 ± 8.8 | 74.8 ± 5.6 | 0 | 97.0 ± 4.4 | 45.9 ± 15.9 | - |
11y | 100 | 100 | 0 | 100 | 81.8 ± 10.5 | 58.9 ± 2.5 |
8 | 100 | 79.8 ± 12.1 | 0 | 100 | 79.5 ± 6.4 | 59.8 ± 5.2 |
9 | 100 | 100 | 0 | 100 | 100 | 100 |
10 | 100 | 77.4 ± 5.0 | 0 | 100 | 100 | 76.2 ± 12.6 |
12a | 100 | 100 | 100 | 100 | 96.6 ± 3.3 | 65.4 ± 3.9 |
12b | 100 | 100 | 100 | 100 | 75.3 ± 2.1 | 49.6 ± 2.1 |
12i | 100 | 100 | 100 | 100 | 60.8 ± 1.7 | 36.9 ± 3.1 |
12o | 100 | 100 | 100 | 100 | 74.4 ± 9.2 | 50.0 ± 3.4 |
12r | 100 | 100 | 100 | 100 | 94.7 ± 5.2 | 73.6 ± 11.6 |
12s | 100 | 100 | 100 | 100 | 93.8 ± 5.8 | 77.8 ± 9.9 |
12t | 100 | 100 | 100 | 95.3 ± 4.3 | 77.6 ± 2.3 | 47.1 ± 2.4 |
12u | 100 | 100 | 100 | 100 | 73.5 ± 7.9 | 45.8 ± 8.9 |
12v | 100 | 100 | 100 | 100 | 69.0 ± 13.5 | 52.6 ± 3.2 |
etoxazole | 100 | 100 | 100 | 100 | 100 | 92.0 ± 7.7 |
Compound | 5 mg/L | 2.5 mg/L | 1.25 mg/L | 0.63 mg/L | 0.31 mg/L | 0.16 mg/L |
---|---|---|---|---|---|---|
9 | 100 | 100 | 100 | 35.6 ± 10.4 | 17.2 ± 13.5 | - |
etoxazole | 92.0 | 86.3 ± 5.8 | 85.7 ± 5.0 | 61.2 ± 12.8 | 53.9 ± 19.3 | 37.1 ± 10.2 |
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Chen, Y.; Tian, J.; Tan, Y.; Liu, Y.; Wang, Q. Design, Synthesis, and Acaricidal Activity of 2,5-Diphenyl-1,3-oxazoline Compounds. Molecules 2024, 29, 4149. https://doi.org/10.3390/molecules29174149
Chen Y, Tian J, Tan Y, Liu Y, Wang Q. Design, Synthesis, and Acaricidal Activity of 2,5-Diphenyl-1,3-oxazoline Compounds. Molecules. 2024; 29(17):4149. https://doi.org/10.3390/molecules29174149
Chicago/Turabian StyleChen, Yuming, Jiarui Tian, Yuhao Tan, Yuxiu Liu, and Qingmin Wang. 2024. "Design, Synthesis, and Acaricidal Activity of 2,5-Diphenyl-1,3-oxazoline Compounds" Molecules 29, no. 17: 4149. https://doi.org/10.3390/molecules29174149