CIESC Journal ›› 2023, Vol. 74 ›› Issue (3): 1390-1398.DOI: 10.11949/0438-1157.20221365
• Material science and engineering, nanotechnology • Previous Articles Next Articles
Feng WANG1,2(), Yu CHEN2, Hongyan PEI2, Dongdong LIU1,2, Jing ZHANG1,2(), Lixin ZHANG1,2()
Received:
2022-10-17
Revised:
2022-12-17
Online:
2023-04-19
Published:
2023-03-05
Contact:
Jing ZHANG, Lixin ZHANG
王锋1,2(), 陈钰2, 裴鸿艳2, 刘东东1,2, 张静1,2(), 张立新1,2()
通讯作者:
张静,张立新
作者简介:
王锋(1991—),男,博士研究生,445765487@qq.com
基金资助:
CLC Number:
Feng WANG, Yu CHEN, Hongyan PEI, Dongdong LIU, Jing ZHANG, Lixin ZHANG. Design, synthesis and anti-fungal activity of 1,2,4-oxadiazole derivatives[J]. CIESC Journal, 2023, 74(3): 1390-1398.
王锋, 陈钰, 裴鸿艳, 刘东东, 张静, 张立新. 1,2,4-𫫇二唑类衍生物的设计、合成及抗菌活性[J]. 化工学报, 2023, 74(3): 1390-1398.
Compound | Reaction time/h | Feature | Melting point/℃ | Yield/% | m/z (calcd.)① |
---|---|---|---|---|---|
5a | 4.0 | white solid | 185.2—185.9 | 75.65 | 340.1(340.1) |
5b | 4.0 | white solid | 188.2—189.0 | 78.25 | 354.1(354.1) |
5c | 3.5 | yellow solid | 184.6—185.2 | 76.52 | 368.1(368.1) |
5d | 5.0 | yellow oil | — | 70.26 | 352.2(352.1) |
5e | 5.0 | white solid | 189.6—190.1 | 72.24 | 370.1(370.1) |
Table 1 Physical data and ESI-MS results of compounds 5a—5e
Compound | Reaction time/h | Feature | Melting point/℃ | Yield/% | m/z (calcd.)① |
---|---|---|---|---|---|
5a | 4.0 | white solid | 185.2—185.9 | 75.65 | 340.1(340.1) |
5b | 4.0 | white solid | 188.2—189.0 | 78.25 | 354.1(354.1) |
5c | 3.5 | yellow solid | 184.6—185.2 | 76.52 | 368.1(368.1) |
5d | 5.0 | yellow oil | — | 70.26 | 352.2(352.1) |
5e | 5.0 | white solid | 189.6—190.1 | 72.24 | 370.1(370.1) |
Compound | |
---|---|
5a | 8.23 (d, J = 8.5 Hz, 2H, Ph-2H), 7.39 (d, J = 8.5 Hz, 2H, Ph-2H), 2.51 (s, 3H, CH3), 1.63—1.59 (m, 1H, CH), 1.18—1.11 (m, 2H, half-CH2CH2), 0.86—0.83 (m, 2H, half-CH2CH2) |
5b | 8.23 (d, J = 8.5 Hz, 2H, Ph-2H), 7.38 (d, J = 8.5 Hz, 2H, Ph-2H), 2.80 (q, J = 7.3 Hz, 2H, CH2), 1.75—1.71 (m, 1H, CH), 1.17 (t, J = 7.3 Hz, 3H, CH3), 1.15—1.12 (m, 2H, half-CH2CH2), 0.87—0.84 (m, 2H, half-CH2CH2) |
5c | 8.22 (d, J = 8.4 Hz, 2H, Ph-2H), 7.36 (d, J = 8.5 Hz, 2H, Ph-2H), 3.35—3.30 (m, 1H, CH), 1.74—1.70 (m, 1H, CH), 1.21[d, J = 6.8 Hz, 6H, (CH3)2], 1.17—1.14 (m, 2H, half-CH2CH2), 0.88—0.85 (m, 2H, half-CH2CH2) |
5d | 8.23 (d, J = 8.4 Hz, 2H, Ph-2H), 7.39 (d, J = 8.5 Hz, 2H, Ph-2H), 6.63 (dd, J = 16.8, 10.3 Hz, 1H, =CH), 6.48 (dd, J = 16.8, 1.6 Hz, 1H, CH), 5.78 (dd, J = 10.3, 1.6 Hz, 1H, =CH), 1.93—1.89 (m, 1H, CH), 1.21—1.18 (m, 2H, half-CH2CH2), 0.94—0.91 (m, 2H, half-CH2CH2) |
5e | 8.17 (d, J = 8.5 Hz, 2H, Ph-2H), 7.30 (d, J = 8.5 Hz, 2H, Ph-2H), 4.23 (q, J = 7.1 Hz, 2H, CH2), 2.83—2.78 (m, 1H, CH), 1.20 (t, J = 7.1 Hz, 3H, CH3), 1.19—1.16 (m, 2H, half-CH2CH2), 1.02—0.99 (m, 2H, half-CH2CH2) |
Table 2 1H NMR data of compounds 5a—5e
Compound | |
---|---|
5a | 8.23 (d, J = 8.5 Hz, 2H, Ph-2H), 7.39 (d, J = 8.5 Hz, 2H, Ph-2H), 2.51 (s, 3H, CH3), 1.63—1.59 (m, 1H, CH), 1.18—1.11 (m, 2H, half-CH2CH2), 0.86—0.83 (m, 2H, half-CH2CH2) |
5b | 8.23 (d, J = 8.5 Hz, 2H, Ph-2H), 7.38 (d, J = 8.5 Hz, 2H, Ph-2H), 2.80 (q, J = 7.3 Hz, 2H, CH2), 1.75—1.71 (m, 1H, CH), 1.17 (t, J = 7.3 Hz, 3H, CH3), 1.15—1.12 (m, 2H, half-CH2CH2), 0.87—0.84 (m, 2H, half-CH2CH2) |
5c | 8.22 (d, J = 8.4 Hz, 2H, Ph-2H), 7.36 (d, J = 8.5 Hz, 2H, Ph-2H), 3.35—3.30 (m, 1H, CH), 1.74—1.70 (m, 1H, CH), 1.21[d, J = 6.8 Hz, 6H, (CH3)2], 1.17—1.14 (m, 2H, half-CH2CH2), 0.88—0.85 (m, 2H, half-CH2CH2) |
5d | 8.23 (d, J = 8.4 Hz, 2H, Ph-2H), 7.39 (d, J = 8.5 Hz, 2H, Ph-2H), 6.63 (dd, J = 16.8, 10.3 Hz, 1H, =CH), 6.48 (dd, J = 16.8, 1.6 Hz, 1H, CH), 5.78 (dd, J = 10.3, 1.6 Hz, 1H, =CH), 1.93—1.89 (m, 1H, CH), 1.21—1.18 (m, 2H, half-CH2CH2), 0.94—0.91 (m, 2H, half-CH2CH2) |
5e | 8.17 (d, J = 8.5 Hz, 2H, Ph-2H), 7.30 (d, J = 8.5 Hz, 2H, Ph-2H), 4.23 (q, J = 7.1 Hz, 2H, CH2), 2.83—2.78 (m, 1H, CH), 1.20 (t, J = 7.1 Hz, 3H, CH3), 1.19—1.16 (m, 2H, half-CH2CH2), 1.02—0.99 (m, 2H, half-CH2CH2) |
Compound | Reaction time/h | Feature | Melting point/℃ | Yield/% | m/z (calcd.) |
---|---|---|---|---|---|
6a | 4.0 | white solid | 185.2—185.6 | 80.45 | 365.2(365.1) |
6b | 5.0 | white solid | 190.5—191.2 | 80.25 | 338.4(338.1) |
6c | 4.0 | yellow solid | 162.6—163.7 | 90.84 | 360.3(360.1) |
6d | 5.0 | white solid | 184.2—185.2 | 84.52 | 380.3(380.1) |
6e | 5.0 | white solid | 183.5—184.2 | 73.69 | 384.2(384.1) |
6f | 5.0 | white solid | 195.2—195.8 | 80.42 | 380.2(380.1) |
6g | 5.0 | white solid | 248.6—249.0 | 70.35 | 384.1(384.1) |
Table 3 Physical data and ESI-MS results of compounds 6a—6g
Compound | Reaction time/h | Feature | Melting point/℃ | Yield/% | m/z (calcd.) |
---|---|---|---|---|---|
6a | 4.0 | white solid | 185.2—185.6 | 80.45 | 365.2(365.1) |
6b | 5.0 | white solid | 190.5—191.2 | 80.25 | 338.4(338.1) |
6c | 4.0 | yellow solid | 162.6—163.7 | 90.84 | 360.3(360.1) |
6d | 5.0 | white solid | 184.2—185.2 | 84.52 | 380.3(380.1) |
6e | 5.0 | white solid | 183.5—184.2 | 73.69 | 384.2(384.1) |
6f | 5.0 | white solid | 195.2—195.8 | 80.42 | 380.2(380.1) |
6g | 5.0 | white solid | 248.6—249.0 | 70.35 | 384.1(384.1) |
Compound | |
---|---|
6a | 8.22 (d, J = 8.4 Hz, 2H, Ph-2H), 7.41 (d, J = 8.4 Hz, 2H, Ph-2H), 2.09—2.05 (m, 2H, CH), 1.21—1.16 [m, 4H, 2(half-CH2CH2)], 0.94—0.91 [m, 4H, 2(half-CH2CH2)] |
6b | 8.24 (d, J = 8.5 Hz, 2H, Ph-2H), 7.34 (d, J = 8.5 Hz, 2H, Ph-2H), 6.56—6.47 (m, 4H, =CH2), 5.80 (t, J = 5.9 Hz, 2H, =CH) |
6c | 8.27 (d, J = 8.3 Hz, 2H, Ph-2H), 8.00 (dd, J = 5.4, 3.1 Hz, 2H, Ph-2H), 7.84 (dd, J = 5.5, 3.1 Hz, 2H, Ph-2H), 7.70 (d, J = 8.3 Hz, 2H, Ph-2H) |
6d | 8.15 (d, J = 8.0 Hz, 1H, Ph-H), 7.24 (d, J = 8.6 Hz, 2H, Ph-2H), 2.69 (s, 3H, CH3), 2.10—2.06 (m, 2H, CH), 1.20—1.15 [m, 4H, 2(half-CH2CH2)], 0.93—0.90 [m, 4H, 2(half-CH2CH2)] |
6e | 8.19 (t, J = 7.9 Hz, 1H, Ph-H), 7.26—7.20 (m, 2H, Ph-2H), 2.09—2.05 (m, 2H, CH), 1.21—1.18 [m, 4H, 2(half-CH2CH2)], 0.97—0.94 [m, 4H, 2(half-CH2CH2)] |
6f | 8.11—8.08 (m, 1H, Ph-H), 8.04 (dd, J = 8.1, 2.0 Hz, 1H, Ph-H), 7.34 (d, J = 8.1 Hz, 1H, Ph-H), 2.31 (s, 3H, CH3), 2.10—2.06 (m, 2H, CH), 1.21—1.12 [m, 4H, 2(half-CH2CH2)], 0.94—0.87 [m, 4H, 2(half-CH2CH2)] |
6g | 8.02 (d, J = 8.2 Hz, 1H, Ph-H), 7.98 (d, J = 9.5 Hz, 1H, Ph-H), 7.45 (t, J = 7.8 Hz, 1H, Ph-H), 2.13—2.10 (m, 2H, CH), 1.22—1.19 [m, 4H, 2(half-CH2CH2)], 0.96—0.93 [m, 4H, 2(half-CH2CH2)]. |
Table 4 1H NMR data of compounds 6a—6g
Compound | |
---|---|
6a | 8.22 (d, J = 8.4 Hz, 2H, Ph-2H), 7.41 (d, J = 8.4 Hz, 2H, Ph-2H), 2.09—2.05 (m, 2H, CH), 1.21—1.16 [m, 4H, 2(half-CH2CH2)], 0.94—0.91 [m, 4H, 2(half-CH2CH2)] |
6b | 8.24 (d, J = 8.5 Hz, 2H, Ph-2H), 7.34 (d, J = 8.5 Hz, 2H, Ph-2H), 6.56—6.47 (m, 4H, =CH2), 5.80 (t, J = 5.9 Hz, 2H, =CH) |
6c | 8.27 (d, J = 8.3 Hz, 2H, Ph-2H), 8.00 (dd, J = 5.4, 3.1 Hz, 2H, Ph-2H), 7.84 (dd, J = 5.5, 3.1 Hz, 2H, Ph-2H), 7.70 (d, J = 8.3 Hz, 2H, Ph-2H) |
6d | 8.15 (d, J = 8.0 Hz, 1H, Ph-H), 7.24 (d, J = 8.6 Hz, 2H, Ph-2H), 2.69 (s, 3H, CH3), 2.10—2.06 (m, 2H, CH), 1.20—1.15 [m, 4H, 2(half-CH2CH2)], 0.93—0.90 [m, 4H, 2(half-CH2CH2)] |
6e | 8.19 (t, J = 7.9 Hz, 1H, Ph-H), 7.26—7.20 (m, 2H, Ph-2H), 2.09—2.05 (m, 2H, CH), 1.21—1.18 [m, 4H, 2(half-CH2CH2)], 0.97—0.94 [m, 4H, 2(half-CH2CH2)] |
6f | 8.11—8.08 (m, 1H, Ph-H), 8.04 (dd, J = 8.1, 2.0 Hz, 1H, Ph-H), 7.34 (d, J = 8.1 Hz, 1H, Ph-H), 2.31 (s, 3H, CH3), 2.10—2.06 (m, 2H, CH), 1.21—1.12 [m, 4H, 2(half-CH2CH2)], 0.94—0.87 [m, 4H, 2(half-CH2CH2)] |
6g | 8.02 (d, J = 8.2 Hz, 1H, Ph-H), 7.98 (d, J = 9.5 Hz, 1H, Ph-H), 7.45 (t, J = 7.8 Hz, 1H, Ph-H), 2.13—2.10 (m, 2H, CH), 1.22—1.19 [m, 4H, 2(half-CH2CH2)], 0.96—0.93 [m, 4H, 2(half-CH2CH2)]. |
目标化合物 | 抑制率/% | ||||
---|---|---|---|---|---|
6.25 mg/L | 3.125 mg/L | 1.5625 mg/L | 0.7825 mg/L | 0.39125 mg/L | |
5a | 75 | 30 | 0 | — | — |
5b | 98 | 60 | 35 | — | — |
5c | 0 | 0 | 0 | — | — |
5d | 85 | 65 | 30 | — | — |
5e | 85 | 50 | 10 | — | — |
6a | 100 | 100 | 99 | 93 | 90 |
6b | 20 | 15 | 0 | — | — |
6c | 50 | 20 | 0 | — | — |
6d | 30 | 0 | 0 | — | — |
6e | 100 | 98 | 60 | — | — |
6f | 78 | 45 | 20 | — | — |
6g | 100 | 95 | 50 | — | — |
苯醚甲环唑 | 95 | 50 | 15 | — | — |
嘧菌酯 | 100 | 100 | 100 | 100 | 98 |
Table 5 Anti-fungal activity against soybean rust by target compounds
目标化合物 | 抑制率/% | ||||
---|---|---|---|---|---|
6.25 mg/L | 3.125 mg/L | 1.5625 mg/L | 0.7825 mg/L | 0.39125 mg/L | |
5a | 75 | 30 | 0 | — | — |
5b | 98 | 60 | 35 | — | — |
5c | 0 | 0 | 0 | — | — |
5d | 85 | 65 | 30 | — | — |
5e | 85 | 50 | 10 | — | — |
6a | 100 | 100 | 99 | 93 | 90 |
6b | 20 | 15 | 0 | — | — |
6c | 50 | 20 | 0 | — | — |
6d | 30 | 0 | 0 | — | — |
6e | 100 | 98 | 60 | — | — |
6f | 78 | 45 | 20 | — | — |
6g | 100 | 95 | 50 | — | — |
苯醚甲环唑 | 95 | 50 | 15 | — | — |
嘧菌酯 | 100 | 100 | 100 | 100 | 98 |
目标化合物 | IC50/(mg/L) | 毒力回归方程 | R |
---|---|---|---|
5a | 4.265 | y = 1.2457x - 0.2664 | 0.9910 |
5b | 2.251 | y = 1.0464x + 0.1255 | 0.9375 |
5d | 2.363 | y = 0.9135x + 0.1479 | 0.9952 |
5e | 3.197 | y = 1.2457x - 0.1331 | 0.9968 |
6c | 6.174 | y = 0.8305x - 0.1776 | 0.9808 |
6e | 1.442 | y = 0.8372x - 0.2205 | 0.9999 |
6f | 3.352 | y = 0.9634x - 0.0001 | 0.9966 |
6g | 1.563 | y = 0.6727x - 0.1391 | 0.9998 |
苯醚甲环唑 | 3.125 | y = 1.3288x - 0.1242 | 0.9916 |
Table 6 IC50 values of some compounds against soybean rust
目标化合物 | IC50/(mg/L) | 毒力回归方程 | R |
---|---|---|---|
5a | 4.265 | y = 1.2457x - 0.2664 | 0.9910 |
5b | 2.251 | y = 1.0464x + 0.1255 | 0.9375 |
5d | 2.363 | y = 0.9135x + 0.1479 | 0.9952 |
5e | 3.197 | y = 1.2457x - 0.1331 | 0.9968 |
6c | 6.174 | y = 0.8305x - 0.1776 | 0.9808 |
6e | 1.442 | y = 0.8372x - 0.2205 | 0.9999 |
6f | 3.352 | y = 0.9634x - 0.0001 | 0.9966 |
6g | 1.563 | y = 0.6727x - 0.1391 | 0.9998 |
苯醚甲环唑 | 3.125 | y = 1.3288x - 0.1242 | 0.9916 |
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