Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2813-2820.DOI: 10.6023/cjoc201903048 Previous Articles Next Articles
ARTICLE
陈英, 李普, 陈梅, 苏时军, 贺军, 张敏, 柳立伟, 薛伟*()
收稿日期:
2019-03-23
修回日期:
2019-04-18
发布日期:
2019-06-12
通讯作者:
薛伟
E-mail:wxue@gzu.edu.cn
基金资助:
Chen Ying, Li Pu, Chen Mei, Su Shijun, He Jun, Zhang Min, Liu Liwei, Xue Wei*()
Received:
2019-03-23
Revised:
2019-04-18
Published:
2019-06-12
Contact:
Xue Wei
E-mail:wxue@gzu.edu.cn
Supported by:
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Chen Ying, Li Pu, Chen Mei, Su Shijun, He Jun, Zhang Min, Liu Liwei, Xue Wei. Syntheses and Biological Activities of 1,4-Pentadien-3-oneDerivatives Containing Thioether Triazole Moiety[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2813-2820.
Compound | R | X. citri | X. oryzae | R. solanacearum | ||||||
---|---|---|---|---|---|---|---|---|---|---|
100 μg/mL | 50 μg/mL | 100 μg/mL | 50 μg/mL | 100 μg/mL | 50 μg/mL | |||||
F1 | Ph | 47.0±1.6 | 36.5±4.0 | 89.5±0.9 | 74.3±0.1 | 54.5±3.4 | 49.8±5.3 | |||
F2 | Thiophen-2-yl | 42.4±2.3 | 39.0±5.0 | 34.7±0.6 | 1.5±0.2 | 32.8±2.1 | 28.3±0.1 | |||
F3 | 3,4-(CH3)2C6H3 | 57.4±4.1 | 41.9±2.7 | 17.7±0.8 | 10.6±1.4 | 75.9±1.5 | 62.4±0.4 | |||
F4 | 4-NO2C6H4 | 72.3±5.3 | 62.8±2.8 | 58.0±0.5 | 41.6±1.2 | 51.6±0.1 | 47.9±0.5 | |||
F5 | 4-ClC6H4 | 68.0±0.9 | 52.3±2.5 | 60.5±1.1 | 48.8±0.5 | 48.3±2.4 | 35.2±1.6 | |||
F6 | 4-FC6H4 | 82.5±0.2 | 78.6±2.9 | 59.0±4.7 | 50.6±3.0 | 76.8±5.4 | 66.3±3.5 | |||
F7 | 2,4-(CH3O)2C6H3 | 71.3±0.9 | 63.5±0.4 | 70.0±0.4 | 62.9±0.9 | 53.2±0.6 | 50.0±3.2 | |||
F8 | 3-NO2C6H4 | 66.9±6.4 | 57.1±1.1 | 60.1±1.6 | 51.7±1.8 | 50.5±3.8 | 41.7±5.2 | |||
F9 | 2-ClC6H4 | 72.6±4.3 | 64.1±2.2 | 56.2±4.7 | 47.6±2.6 | 41.6±0.9 | 35.2±0.5 | |||
F10 | 4-CH3OC6H4 | 70.9±2.9 | 64.5±5.4 | 61.7±0.9 | 57.4±2.6 | 48.3±2.5 | 32.4±3.5 | |||
F11 | 4-Methylthiazol-5-yl | 63.3±5.6 | 56.5±1.2 | 46.9±2.8 | 44.7±0.8 | 44.9±1.6 | 36.3±1.3 | |||
F12 | Furan-2-yl | 55.3±1.3 | 48.1±2.5 | 68.6±4.2 | 56.7±0.2 | 37.4±0.7 | 23.2±4.8 | |||
F13 | 3,4-(CH3O)2C6H3 | 38.5±4.0 | 25.0±1.6 | 66.2±0.4 | 60.4±3.9 | 54.8±1.9 | 42.1±1.3 | |||
F14 | 4-BrC6H4 | 73.6±6.1 | 65.8±2.7 | 62.2±0.7 | 54.9±0.4 | 50.2±0.1 | 47.1±7.2 | |||
F15 | 2,4-Cl2C6H3 | 56.7±2.4 | 45.7±4.9 | 61.7±0.4 | 54.9±0.6 | 55.9±1.1 | 42.4±0.6 | |||
F16 | 4-CH3C6H4 | 77.4±4.0 | 68.7±1.4 | 53.0±1.9 | 44.6±0.6 | 51.0±1.8 | 33.9±2.3 | |||
Bismerthiazolb | — | 59.5±7.7 | 49.5±5.7 | 56.0±1.2 | 33.8±2.0 | 61.1±6.2 | 49.5±5.3 |
Compound | R | X. citri | X. oryzae | R. solanacearum | ||||||
---|---|---|---|---|---|---|---|---|---|---|
100 μg/mL | 50 μg/mL | 100 μg/mL | 50 μg/mL | 100 μg/mL | 50 μg/mL | |||||
F1 | Ph | 47.0±1.6 | 36.5±4.0 | 89.5±0.9 | 74.3±0.1 | 54.5±3.4 | 49.8±5.3 | |||
F2 | Thiophen-2-yl | 42.4±2.3 | 39.0±5.0 | 34.7±0.6 | 1.5±0.2 | 32.8±2.1 | 28.3±0.1 | |||
F3 | 3,4-(CH3)2C6H3 | 57.4±4.1 | 41.9±2.7 | 17.7±0.8 | 10.6±1.4 | 75.9±1.5 | 62.4±0.4 | |||
F4 | 4-NO2C6H4 | 72.3±5.3 | 62.8±2.8 | 58.0±0.5 | 41.6±1.2 | 51.6±0.1 | 47.9±0.5 | |||
F5 | 4-ClC6H4 | 68.0±0.9 | 52.3±2.5 | 60.5±1.1 | 48.8±0.5 | 48.3±2.4 | 35.2±1.6 | |||
F6 | 4-FC6H4 | 82.5±0.2 | 78.6±2.9 | 59.0±4.7 | 50.6±3.0 | 76.8±5.4 | 66.3±3.5 | |||
F7 | 2,4-(CH3O)2C6H3 | 71.3±0.9 | 63.5±0.4 | 70.0±0.4 | 62.9±0.9 | 53.2±0.6 | 50.0±3.2 | |||
F8 | 3-NO2C6H4 | 66.9±6.4 | 57.1±1.1 | 60.1±1.6 | 51.7±1.8 | 50.5±3.8 | 41.7±5.2 | |||
F9 | 2-ClC6H4 | 72.6±4.3 | 64.1±2.2 | 56.2±4.7 | 47.6±2.6 | 41.6±0.9 | 35.2±0.5 | |||
F10 | 4-CH3OC6H4 | 70.9±2.9 | 64.5±5.4 | 61.7±0.9 | 57.4±2.6 | 48.3±2.5 | 32.4±3.5 | |||
F11 | 4-Methylthiazol-5-yl | 63.3±5.6 | 56.5±1.2 | 46.9±2.8 | 44.7±0.8 | 44.9±1.6 | 36.3±1.3 | |||
F12 | Furan-2-yl | 55.3±1.3 | 48.1±2.5 | 68.6±4.2 | 56.7±0.2 | 37.4±0.7 | 23.2±4.8 | |||
F13 | 3,4-(CH3O)2C6H3 | 38.5±4.0 | 25.0±1.6 | 66.2±0.4 | 60.4±3.9 | 54.8±1.9 | 42.1±1.3 | |||
F14 | 4-BrC6H4 | 73.6±6.1 | 65.8±2.7 | 62.2±0.7 | 54.9±0.4 | 50.2±0.1 | 47.1±7.2 | |||
F15 | 2,4-Cl2C6H3 | 56.7±2.4 | 45.7±4.9 | 61.7±0.4 | 54.9±0.6 | 55.9±1.1 | 42.4±0.6 | |||
F16 | 4-CH3C6H4 | 77.4±4.0 | 68.7±1.4 | 53.0±1.9 | 44.6±0.6 | 51.0±1.8 | 33.9±2.3 | |||
Bismerthiazolb | — | 59.5±7.7 | 49.5±5.7 | 56.0±1.2 | 33.8±2.0 | 61.1±6.2 | 49.5±5.3 |
Compound | R | Toxic regression equation | r | EC50/(μg?mL–1) |
---|---|---|---|---|
F4 | 4-O2NC6H4 | y=0.7252x+4.1219 | 0.9871 | 16.3±2.5 |
F5 | 4-ClC6H4 | y=0.9076x+3.6020 | 0.9559 | 34.7±2.3 |
F6 | 4-FC6H4 | y=0.9529x+4.0511 | 0.9581 | 9.9±2.1 |
F7 | 2,4-(CH3O)2C6H3 | y=0.6956x+4.1554 | 0.9889 | 16.4±1.0 |
F8 | 3-O2NC6H4 | y=0.9427x+3.5545 | 0.9965 | 34.2±2.4 |
F9 | 2-ClC6H4 | y=0.8344x+3.9314 | 0.9978 | 19.1±2.7 |
F10 | 4-CH3OC6H4 | y=0.7527x+4.0683 | 0.9897 | 17.3±2.8 |
F14 | 4-BrC6H4 | y=0.8865x+3.8683 | 0.9899 | 18.9±2.8 |
F16 | 4-CH3C6H4 | y=0.9412x+3.8669 | 0.9965 | 15.9±1.9 |
Bismerthiazola | — | y=0.8357x+3.5466 | 0.9876 | 54.9±1.4 |
Compound | R | Toxic regression equation | r | EC50/(μg?mL–1) |
---|---|---|---|---|
F4 | 4-O2NC6H4 | y=0.7252x+4.1219 | 0.9871 | 16.3±2.5 |
F5 | 4-ClC6H4 | y=0.9076x+3.6020 | 0.9559 | 34.7±2.3 |
F6 | 4-FC6H4 | y=0.9529x+4.0511 | 0.9581 | 9.9±2.1 |
F7 | 2,4-(CH3O)2C6H3 | y=0.6956x+4.1554 | 0.9889 | 16.4±1.0 |
F8 | 3-O2NC6H4 | y=0.9427x+3.5545 | 0.9965 | 34.2±2.4 |
F9 | 2-ClC6H4 | y=0.8344x+3.9314 | 0.9978 | 19.1±2.7 |
F10 | 4-CH3OC6H4 | y=0.7527x+4.0683 | 0.9897 | 17.3±2.8 |
F14 | 4-BrC6H4 | y=0.8865x+3.8683 | 0.9899 | 18.9±2.8 |
F16 | 4-CH3C6H4 | y=0.9412x+3.8669 | 0.9965 | 15.9±1.9 |
Bismerthiazola | — | y=0.8357x+3.5466 | 0.9876 | 54.9±1.4 |
Compound | R | Toxic regression equation | r | EC50/(μg?mL–1) |
---|---|---|---|---|
F1 | Ph | y=1.0838x+3.9378 | 0.9488 | 9.6±1.9 |
F5 | 4-ClC6H4 | y=0.7955x+3.7062 | 0.9066 | 42.3±0.5 |
F7 | 2,4-(CH3O)2C6H3 | y=0.8195x+3.9491 | 0.9250 | 19.2±0.8 |
F8 | 3-O2NC6H4 | y=0.8219x+3.6715 | 0.9099 | 41.3±1.4 |
F10 | 4-CH3OC6H4 | y=0.8897x+3.6013 | 0.9524 | 37.3±1.5 |
F12 | Furan-2-yl | y=0.9935x+3.5123 | 0.9899 | 31.4±2.2 |
F13 | 3,4-(CH3O)2C6H3 | y=0.9779x+3.5713 | 0.9402 | 28.9±1.4 |
F14 | 4-BrC6H4 | y=0.8431x+3.6698 | 0.9886 | 37.8±0.8 |
F15 | 2,4-Cl2C6H3 | y=0.4375x+4.4190 | 0.9756 | 21.3±0.8 |
Bismerthiazola | — | y=2.8364x+0.5935 | 0.9897 | 69.3±2.0 |
Compound | R | Toxic regression equation | r | EC50/(μg?mL–1) |
---|---|---|---|---|
F1 | Ph | y=1.0838x+3.9378 | 0.9488 | 9.6±1.9 |
F5 | 4-ClC6H4 | y=0.7955x+3.7062 | 0.9066 | 42.3±0.5 |
F7 | 2,4-(CH3O)2C6H3 | y=0.8195x+3.9491 | 0.9250 | 19.2±0.8 |
F8 | 3-O2NC6H4 | y=0.8219x+3.6715 | 0.9099 | 41.3±1.4 |
F10 | 4-CH3OC6H4 | y=0.8897x+3.6013 | 0.9524 | 37.3±1.5 |
F12 | Furan-2-yl | y=0.9935x+3.5123 | 0.9899 | 31.4±2.2 |
F13 | 3,4-(CH3O)2C6H3 | y=0.9779x+3.5713 | 0.9402 | 28.9±1.4 |
F14 | 4-BrC6H4 | y=0.8431x+3.6698 | 0.9886 | 37.8±0.8 |
F15 | 2,4-Cl2C6H3 | y=0.4375x+4.4190 | 0.9756 | 21.3±0.8 |
Bismerthiazola | — | y=2.8364x+0.5935 | 0.9897 | 69.3±2.0 |
Compound | R | Toxic regression equation | r | EC50/(μg?mL–1) |
---|---|---|---|---|
F3 | 3,4-(CH3)2C6H3 | y=0.7267x+4.1628 | 0.9547 | 14.2±3.3 |
F6 | 4-FC6H4 | y=0.8243x+4.0431 | 0.9917 | 14.5±4.9 |
Bismerthiazola | — | y=0.9991x+3.2599 | 0.9399 | 82.6±0.9 |
Compound | R | Toxic regression equation | r | EC50/(μg?mL–1) |
---|---|---|---|---|
F3 | 3,4-(CH3)2C6H3 | y=0.7267x+4.1628 | 0.9547 | 14.2±3.3 |
F6 | 4-FC6H4 | y=0.8243x+4.0431 | 0.9917 | 14.5±4.9 |
Bismerthiazola | — | y=0.9991x+3.2599 | 0.9399 | 82.6±0.9 |
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