Synthesis and Fungicidal Activity of Novel 2,3-Disubstituted-1,3-benzoxazines
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
Entry | R | R1 | R2 | Product | Yield/% b |
---|---|---|---|---|---|
1 | H | 4-CH3C6H4 | 4-F | 6a | 57 |
2 | H | C6H5 | 4-F | 6b | 55 |
3 | H | 4-CH3OC6H4 | 4-F | 6c | 53 |
4 | H | 4-ClC6H4 | 4-F | 6d | 59 |
5 | H | CH2COOCH3 | 4-F | 6e | 62 |
6 | H | 4-ClC6H4 | 3-NO2 | 6f | 67 |
7 | H | 4-ClC6H4 | H | 6g | 57 |
8 | CH3 | 4-CH3C6H4 | 2-NO2 | 6h | 75 |
9 | CH3 | 4-CH3C6H4 | 3-NO2 | 6i | 78 |
10 | CH3 | 4-CH3C6H4 | 4-NO2 | 6j | 78 |
11 | H | C6H5 | 4-NO2 | 6k | 73 |
12 | H | CH2COOCH3 | 2-NO2 | 6l | 88 |
14 | H | CH2COOCH3 | 3-NO2 | 6n | 90 |
2.2. Fungicidal Activity Assay
Compd. | Phytophythor a capsici /% | Gibberella zeae /% | Sclerotonia sclerotiorum /% | Alternaria alternata /% | Botrytis cinerea /% | Rhizoctonia solani /% | |||
---|---|---|---|---|---|---|---|---|---|
6a | 39 | 40 | 81 | 13 | 28 | 0 | |||
6b | 21 | 37 | 69 | 0 | 29 | 0 | |||
6c | 18 | 40 | 28 | 0 | 14 | 0 | |||
6d | 55 | 49 | 89 | 21 | 52 | 0 | |||
6e | 21 | 35 | 31 | 0 | 7 | 0 | |||
6f | 24 | 40 | 89 | 25 | 46 | 0 | |||
6g | 27 | 40 | 48 | 17 | 51 | 0 | |||
6h | 9 | 26 | 0 | 8 | 0 | 0 | |||
6i | 3 | 23 | 52 | 13 | 7 | 0 | |||
6j | 0 | 16 | 37 | 21 | 14 | 50 | |||
6k | 0 | 0 | 91 | 0 | 25 | 100 | |||
6l | 0 | 0 | 52 | 0 | 12 | 100 | |||
6m | 0 | 33 | 37 | 13 | 19 | 0 | |||
6n | 0 | 0 | 83 | 25 | 19 | 100 | |||
6o a | 28 | 31 | 60 | 11 | 19 | 100 | |||
6p a | 37 | 10 | 0 | 18 | 14 | 50 |
3. Experimental
3.1. Materials and Reagents
3.2. Chemical Synthesis
3.2.1. Synthesis of 2-(N-Substituted aminomethyl) Phenols 4a–f [21,26,27]
3.2.2. Synthesis of 3,4-Dihydro-2H-1,3-benzoxazines 6a–n
3.3. Biological Assay [28]
4. Conclusions
Acknowledgments
References
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Tang, Z.; Zhu, Z.; Xia, Z.; Liu, H.; Chen, J.; Xiao, W.; Ou, X. Synthesis and Fungicidal Activity of Novel 2,3-Disubstituted-1,3-benzoxazines. Molecules 2012, 17, 8174-8185. https://doi.org/10.3390/molecules17078174
Tang Z, Zhu Z, Xia Z, Liu H, Chen J, Xiao W, Ou X. Synthesis and Fungicidal Activity of Novel 2,3-Disubstituted-1,3-benzoxazines. Molecules. 2012; 17(7):8174-8185. https://doi.org/10.3390/molecules17078174
Chicago/Turabian StyleTang, Zilong, Zhonghua Zhu, Zanwen Xia, Hanwen Liu, Jinwen Chen, Wenjing Xiao, and Xiaoming Ou. 2012. "Synthesis and Fungicidal Activity of Novel 2,3-Disubstituted-1,3-benzoxazines" Molecules 17, no. 7: 8174-8185. https://doi.org/10.3390/molecules17078174