Chem. J. Chinese Universities ›› 2015, Vol. 36 ›› Issue (5): 907.doi: 10.7503/cjcu20141121
• Organic Chemistry • Previous Articles Next Articles
CHEN Wei, WEI Wei, LI Yuxin, WAN Yingying, LIU Qiaoxia, LI Yonghong, YU Shujing, LI Zhengming*()
Received:
2014-12-22
Online:
2015-05-10
Published:
2015-04-08
Contact:
LI Zhengming
E-mail:nkzml@vip.163.com
Supported by:
CLC Number:
TrendMD:
CHEN Wei, WEI Wei, LI Yuxin, WAN Yingying, LIU Qiaoxia, LI Yonghong, YU Shujing, LI Zhengming. Synthesis and Biological Activity of 2-Methyl-6-nitrobenzenesulfonylurea Derivatives†[J]. Chem. J. Chinese Universities, 2015, 36(5): 907.
Compd. | Yield(%) | m.p./℃ | HRMS(calcd.), m/z [M+H]+ | Compd. | Yield(%) | m.p./℃ | HRMS(calcd.), m/z [M+H]+ |
---|---|---|---|---|---|---|---|
4a | 64.0 | 228—230 | 372.0166(372.0169) | 4i | 84.7 | 191—193 | 398.0589(398.0593) |
4b | 76.2 | 212—214 | 352.0712(352.0716) | 4j | 63.4 | 211—212 | 386.0326(386.0326) |
4c | 73.2 | 198—199 | 368.0663(368.0665) | 4k | 49.6 | 209—210 | 402.0275(402.0275) |
4d | 80.1 | 203—205 | 382.0817(382.0821) | 4l | 68.4 | 221—223 | 398.0768(398.0770) |
4e | 58.4 | 220—221 | 384.0433(384.0436) | 4m | 74.4 | 179—180 | 414.0538(414.0542) |
4f | 63.2 | 226—227 | 406.0432(406.0433) | 4n | 63.2 | 208—209 | 368.0656(368.0665) |
4g | 73.0 | 216—218 | 366.0870(366.0872) | 4o | 71.3 | 191—193 | 383.0763(383.0774) |
4h | 74.3 | 183—184 | 380.0820(380.0821) | 4p | 67.5 | 195—197 | 412.1031(412.1039) |
Table 1 Yields, melting points and HRMS data of compounds 4a—4p*
Compd. | Yield(%) | m.p./℃ | HRMS(calcd.), m/z [M+H]+ | Compd. | Yield(%) | m.p./℃ | HRMS(calcd.), m/z [M+H]+ |
---|---|---|---|---|---|---|---|
4a | 64.0 | 228—230 | 372.0166(372.0169) | 4i | 84.7 | 191—193 | 398.0589(398.0593) |
4b | 76.2 | 212—214 | 352.0712(352.0716) | 4j | 63.4 | 211—212 | 386.0326(386.0326) |
4c | 73.2 | 198—199 | 368.0663(368.0665) | 4k | 49.6 | 209—210 | 402.0275(402.0275) |
4d | 80.1 | 203—205 | 382.0817(382.0821) | 4l | 68.4 | 221—223 | 398.0768(398.0770) |
4e | 58.4 | 220—221 | 384.0433(384.0436) | 4m | 74.4 | 179—180 | 414.0538(414.0542) |
4f | 63.2 | 226—227 | 406.0432(406.0433) | 4n | 63.2 | 208—209 | 368.0656(368.0665) |
4g | 73.0 | 216—218 | 366.0870(366.0872) | 4o | 71.3 | 191—193 | 383.0763(383.0774) |
4h | 74.3 | 183—184 | 380.0820(380.0821) | 4p | 67.5 | 195—197 | 412.1031(412.1039) |
Compd. | 1H NMR(400 MHz), δ |
---|---|
4aa | 12.42(br, 1H, SO2NH),10.97(s, 1H, CONH-Pyrim), 8.69(d, J=5.4 Hz, 1H, Pyrim-H), 7.82—7.75(m, 2H, Ph-H), 7.71(dd, J=6.6, 2.1 Hz, 1H, Ph-H), 7.41(d, J=5.4 Hz, 1H, Pyrim-H), 2.76(s, 3H, Ph-CH3) |
4bb | 13.40(s, 1H, SO2NH), 9.58(s, 1H, CONH-Pyrim), 8.57(d, J=5.1 Hz, 1H, Pyrim-H), 7.78(d, J=7.8 Hz, 1H, Ph-H), 7.73—7.62(m, 2H, Ph-H), 7.15(d, J=5.1 Hz, 1H, Pyrim-H), 2.91(s, 3H, Ph-CH3), 2.54(s, 3H, Pyrim-CH3) |
4cb | 13.40(br, 1H, SO2NH), 9.60(br, 1H, CONH-Pyrim), 8.43(d, J=6.0 Hz, 1H, Pyrim-H), 7.77(d, J=7.9 Hz, 1H, Ph-H), 7.70—7.64(m, 2H, Ph-H), 6.64(d, J=6.0 Hz, 1H, Pyrim-H), 3.99(s, 3H, Pyrim-OCH3), 2.89(s, 3H, Ph-CH3) |
4db | 13.44(br, 1H, SO2NH), 9.57(br, 1H, CONH-Pyrim), 8.42(d, J=6.0 Hz, 1H, Pyrim-H), 7.77(t, J=7.8 Hz, 1H, Ph-H), 7.63—7.69(m, 2H, Ph-H), 6.61(d, J=6.0 Hz, 1H, Pyrim-H), 4.43(q, J=7.0 Hz, 2H, OCH2CH3), 2.89(s, 3H, Ph-CH3), 1.38(t, J=7.0 Hz, 3H, OCH2CH3) |
4eb | 13.15(br, 1H, SO2NH), 9.67(br, 1H, CONH-Pyrim), 8.35(d, J=5.6 Hz, 1H, Pyrim-H), 7.78(d, J=7.8 Hz, 1H, Ph-H), 7.72—7.66(m, 2H, Ph-H), 7.15(d, J=5.6 Hz, 1H, Pyrim-H), 2.90(s, 3H, Ph-CH3), 2.60(s, 3H, SCH3) |
4fa | 12.31(br, 1H, SO2NH), 10.91(s, 1H, CONH-Pyrim), 9.04(d, J=4.5 Hz, 1H, Pyrim-H), 7.81—7.62(m, 4H, Ph-H), 2.75(s, 3H, Ph-CH3) |
4gb | 13.72(br, 1H, SO2NH), 9.40(s, 1H, CONH-Pyrim), 7.77(d, J=7.7 Hz, 1H, Ph-H), 7.71—7.65(m, 2H, Ph-H), 7.01(s, 1H, Pyrim-H), 2.92(s, 3H, Ph-CH3), 2.47(s, 6H, 2Pyrim-CH3) |
4hb | 13.75(br, 1H, SO2NH), 9.50(br, 1H, CONH-Pyrim), 7.79(t, J=7.8 Hz, 1H, Ph-H), 7.71—7.66(m, 2H, Ph-H), 6.51(s, 1H, Pyrim-H), 3.95(s, 3H, Pyrim-OCH3), 2.92(s, 3H, Ph-CH3), 2.47(s, 3H, Pyrim-CH3) |
4ia | 13.62(s, 1H, SO2NH), 10.87(s, 1H, CONH-Pyrim), 7.74—7.68(m, 3H, Ph-H), 7.11(s, 1H, Pyrim-H), 2.76(s, 3H, SCH3), 2.55(s, 3H, Ph-CH3), 2.38(s, 3H, Pyrim-CH3) |
4jb | 13.02(br, 1H, SO2NH), 9.77(br, 1H, CONH-Pyrim), 7.81(t, J=7.8 Hz, 1H, Ph-H), 7.73—7.68(m, 2H, Ph-H), 7.26(s, 1H, Pyrim-H), 2.93(s, 3H, Ph-CH3), 2.59(s, 3H, Pyrim-CH3) |
4kb | 12.48(br, 1H, SO2NH), 9.81(br, 1H, CONH-Pyrim), 7.83(t, J=7.8 Hz, 1H, Ph-H), 7.75—7.70(m, 2H, Ph-H), 6.74(s, 1H, Pyrim-H), 4.08(s, 3H, Pyrim-OCH3), 2.94(s, 3H, Ph-CH3) |
4lc | 12.88(s, 1H, CONH-Pyrim), 7.59—7.52(m, 2H, Ph-H), 7.44(d, J=7.5 Hz, 1H, Ph-H), 7.30(br, 1H, SO2NH), 5.81(s, 1H, Pyrim-H), 3.97(s, 6H, 2Pyrim-OCH3), 2.98(s, 3H, Ph-CH3) |
4mc | 12.91(s, 1H, SO2NH), 7.58(t, J=7.7 Hz, 1H, Ph-H), 7.52(d, J=7.4 Hz, 1H, Ph-H), 7.43(d, J=7.5 Hz, 1H, Ph-H), 7.37(s, 1H, CONH-Pyrim), 6.32(s, 1H, Pyrim-H), 3.96(s, 3H, Pyrim-OCH3), 2.96(s, 3H, Pyrim-SCH3), 2.55(s, 3H, Ph-CH3) |
4nb | 12.40(br, 1H, SO2NH), 9.44(s, 1H, CONH-Pyrim), 8.61(s, 1H, Pyrim-H), 7.80(t, J=7.8 Hz, 1H, Ph-H), 7.72—7.66(m, 2H, Ph-H), 6.68(s, 1H, Pyrim-H), 3.97(s, 3H, Pyrim-OCH3), 2.89(s, 3H, Ph-CH3) |
4ob | 13.07(br, 1H, SO2NH), 9.92(s, 1H, CONH-Pyrim), 7.82—7.72(m, 3H, Ph-H), 4.03(s, 3H, Triazine-OCH3), 2.92(s, 3H, Ph-CH3), 2.55(s, 3H, Triazine-CH3) |
4pa | 13.63(br, 1H, SO2NH), 10.81(s, 1H, CONH-Pyrim), 8.36(br, 1H, NHCH3), 7.71—7.63(m, 3H, Ph-H), 4.30(q, J=7.1 Hz, 2H, OCH2CH3), 2.83(s, 3H, NHCH3), 2.75(s, 3H, Ph-CH3), 1.30(t, J=7.1 Hz, 3H, OCH2CH3) |
Table 2 1H NMR data of compounds 4a—4p
Compd. | 1H NMR(400 MHz), δ |
---|---|
4aa | 12.42(br, 1H, SO2NH),10.97(s, 1H, CONH-Pyrim), 8.69(d, J=5.4 Hz, 1H, Pyrim-H), 7.82—7.75(m, 2H, Ph-H), 7.71(dd, J=6.6, 2.1 Hz, 1H, Ph-H), 7.41(d, J=5.4 Hz, 1H, Pyrim-H), 2.76(s, 3H, Ph-CH3) |
4bb | 13.40(s, 1H, SO2NH), 9.58(s, 1H, CONH-Pyrim), 8.57(d, J=5.1 Hz, 1H, Pyrim-H), 7.78(d, J=7.8 Hz, 1H, Ph-H), 7.73—7.62(m, 2H, Ph-H), 7.15(d, J=5.1 Hz, 1H, Pyrim-H), 2.91(s, 3H, Ph-CH3), 2.54(s, 3H, Pyrim-CH3) |
4cb | 13.40(br, 1H, SO2NH), 9.60(br, 1H, CONH-Pyrim), 8.43(d, J=6.0 Hz, 1H, Pyrim-H), 7.77(d, J=7.9 Hz, 1H, Ph-H), 7.70—7.64(m, 2H, Ph-H), 6.64(d, J=6.0 Hz, 1H, Pyrim-H), 3.99(s, 3H, Pyrim-OCH3), 2.89(s, 3H, Ph-CH3) |
4db | 13.44(br, 1H, SO2NH), 9.57(br, 1H, CONH-Pyrim), 8.42(d, J=6.0 Hz, 1H, Pyrim-H), 7.77(t, J=7.8 Hz, 1H, Ph-H), 7.63—7.69(m, 2H, Ph-H), 6.61(d, J=6.0 Hz, 1H, Pyrim-H), 4.43(q, J=7.0 Hz, 2H, OCH2CH3), 2.89(s, 3H, Ph-CH3), 1.38(t, J=7.0 Hz, 3H, OCH2CH3) |
4eb | 13.15(br, 1H, SO2NH), 9.67(br, 1H, CONH-Pyrim), 8.35(d, J=5.6 Hz, 1H, Pyrim-H), 7.78(d, J=7.8 Hz, 1H, Ph-H), 7.72—7.66(m, 2H, Ph-H), 7.15(d, J=5.6 Hz, 1H, Pyrim-H), 2.90(s, 3H, Ph-CH3), 2.60(s, 3H, SCH3) |
4fa | 12.31(br, 1H, SO2NH), 10.91(s, 1H, CONH-Pyrim), 9.04(d, J=4.5 Hz, 1H, Pyrim-H), 7.81—7.62(m, 4H, Ph-H), 2.75(s, 3H, Ph-CH3) |
4gb | 13.72(br, 1H, SO2NH), 9.40(s, 1H, CONH-Pyrim), 7.77(d, J=7.7 Hz, 1H, Ph-H), 7.71—7.65(m, 2H, Ph-H), 7.01(s, 1H, Pyrim-H), 2.92(s, 3H, Ph-CH3), 2.47(s, 6H, 2Pyrim-CH3) |
4hb | 13.75(br, 1H, SO2NH), 9.50(br, 1H, CONH-Pyrim), 7.79(t, J=7.8 Hz, 1H, Ph-H), 7.71—7.66(m, 2H, Ph-H), 6.51(s, 1H, Pyrim-H), 3.95(s, 3H, Pyrim-OCH3), 2.92(s, 3H, Ph-CH3), 2.47(s, 3H, Pyrim-CH3) |
4ia | 13.62(s, 1H, SO2NH), 10.87(s, 1H, CONH-Pyrim), 7.74—7.68(m, 3H, Ph-H), 7.11(s, 1H, Pyrim-H), 2.76(s, 3H, SCH3), 2.55(s, 3H, Ph-CH3), 2.38(s, 3H, Pyrim-CH3) |
4jb | 13.02(br, 1H, SO2NH), 9.77(br, 1H, CONH-Pyrim), 7.81(t, J=7.8 Hz, 1H, Ph-H), 7.73—7.68(m, 2H, Ph-H), 7.26(s, 1H, Pyrim-H), 2.93(s, 3H, Ph-CH3), 2.59(s, 3H, Pyrim-CH3) |
4kb | 12.48(br, 1H, SO2NH), 9.81(br, 1H, CONH-Pyrim), 7.83(t, J=7.8 Hz, 1H, Ph-H), 7.75—7.70(m, 2H, Ph-H), 6.74(s, 1H, Pyrim-H), 4.08(s, 3H, Pyrim-OCH3), 2.94(s, 3H, Ph-CH3) |
4lc | 12.88(s, 1H, CONH-Pyrim), 7.59—7.52(m, 2H, Ph-H), 7.44(d, J=7.5 Hz, 1H, Ph-H), 7.30(br, 1H, SO2NH), 5.81(s, 1H, Pyrim-H), 3.97(s, 6H, 2Pyrim-OCH3), 2.98(s, 3H, Ph-CH3) |
4mc | 12.91(s, 1H, SO2NH), 7.58(t, J=7.7 Hz, 1H, Ph-H), 7.52(d, J=7.4 Hz, 1H, Ph-H), 7.43(d, J=7.5 Hz, 1H, Ph-H), 7.37(s, 1H, CONH-Pyrim), 6.32(s, 1H, Pyrim-H), 3.96(s, 3H, Pyrim-OCH3), 2.96(s, 3H, Pyrim-SCH3), 2.55(s, 3H, Ph-CH3) |
4nb | 12.40(br, 1H, SO2NH), 9.44(s, 1H, CONH-Pyrim), 8.61(s, 1H, Pyrim-H), 7.80(t, J=7.8 Hz, 1H, Ph-H), 7.72—7.66(m, 2H, Ph-H), 6.68(s, 1H, Pyrim-H), 3.97(s, 3H, Pyrim-OCH3), 2.89(s, 3H, Ph-CH3) |
4ob | 13.07(br, 1H, SO2NH), 9.92(s, 1H, CONH-Pyrim), 7.82—7.72(m, 3H, Ph-H), 4.03(s, 3H, Triazine-OCH3), 2.92(s, 3H, Ph-CH3), 2.55(s, 3H, Triazine-CH3) |
4pa | 13.63(br, 1H, SO2NH), 10.81(s, 1H, CONH-Pyrim), 8.36(br, 1H, NHCH3), 7.71—7.63(m, 3H, Ph-H), 4.30(q, J=7.1 Hz, 2H, OCH2CH3), 2.83(s, 3H, NHCH3), 2.75(s, 3H, Ph-CH3), 1.30(t, J=7.1 Hz, 3H, OCH2CH3) |
Compd. | Brassica napus | Amaranthus retroflexus | Echinochloa crusgalli | Digitariasanguinalis | ||||
---|---|---|---|---|---|---|---|---|
Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | |
4a | 98.0 | 100 | 100 | 100 | 39.1 | 29.8 | 26.5 | 43.0 |
4b | 100 | 100 | 100 | 100 | 100 | 85.7 | 100 | 100 |
4c | 100 | 100 | 100 | 100 | 94.1 | 32.2 | 40.7 | 10.4 |
4d | 100 | 100 | 81.0 | 77.4 | 50.8 | 30.7 | 15.8 | 11.3 |
4e | 100 | 100 | 100 | 73.2 | 30.0 | 0 | 9.1 | 0 |
4f | 100 | 100 | 100 | 100 | 40.9 | 29.8 | 17.0 | 21.8 |
4g | 100 | 100 | 100 | 100 | 100 | 80.7 | 49.1 | 90.4 |
4h | 100 | 100 | 100 | 100 | 100 | 48.0 | 100 | 88.4 |
4i | 100 | 100 | 93.8 | 100 | 80.8 | 32.2 | 47.9 | 37.9 |
4j | 100 | 96.1 | 100 | 100 | 47.0 | 45.6 | 15.3 | 46.3 |
4k | 100 | 100 | 100 | 92.6 | 99.5 | 82.1 | 12.3 | 17.5 |
4l | 100 | 100 | 100 | 100 | 99.1 | 42.0 | 29.8 | 35.8 |
4m | 100 | 100 | 85.0 | 80.1 | 82.7 | 46.1 | 24.5 | 23.5 |
4n | 100 | 100 | 28.6 | 89.6 | 45.7 | 21.2 | 14.2 | 18.2 |
4o | 100 | 100 | 94.6 | 100 | 38.7 | 26.1 | 71.2 | 25.4 |
4p | 100 | 100 | 100 | 100 | 100 | 42.0 | 37.2 | 80.9 |
Monosulfuron | 100 | 100 | 100 | 100 | 100 | 74.1 | 100 | 86.1 |
Chlorsulfuron | 100 | 100 | 100 | 100 | 96.3 | 73.1 | 100 | 22.7 |
Table 3 Herbicidal activities(%) of compounds 4a—4p by pot-culture method(300 g/ha)
Compd. | Brassica napus | Amaranthus retroflexus | Echinochloa crusgalli | Digitariasanguinalis | ||||
---|---|---|---|---|---|---|---|---|
Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | |
4a | 98.0 | 100 | 100 | 100 | 39.1 | 29.8 | 26.5 | 43.0 |
4b | 100 | 100 | 100 | 100 | 100 | 85.7 | 100 | 100 |
4c | 100 | 100 | 100 | 100 | 94.1 | 32.2 | 40.7 | 10.4 |
4d | 100 | 100 | 81.0 | 77.4 | 50.8 | 30.7 | 15.8 | 11.3 |
4e | 100 | 100 | 100 | 73.2 | 30.0 | 0 | 9.1 | 0 |
4f | 100 | 100 | 100 | 100 | 40.9 | 29.8 | 17.0 | 21.8 |
4g | 100 | 100 | 100 | 100 | 100 | 80.7 | 49.1 | 90.4 |
4h | 100 | 100 | 100 | 100 | 100 | 48.0 | 100 | 88.4 |
4i | 100 | 100 | 93.8 | 100 | 80.8 | 32.2 | 47.9 | 37.9 |
4j | 100 | 96.1 | 100 | 100 | 47.0 | 45.6 | 15.3 | 46.3 |
4k | 100 | 100 | 100 | 92.6 | 99.5 | 82.1 | 12.3 | 17.5 |
4l | 100 | 100 | 100 | 100 | 99.1 | 42.0 | 29.8 | 35.8 |
4m | 100 | 100 | 85.0 | 80.1 | 82.7 | 46.1 | 24.5 | 23.5 |
4n | 100 | 100 | 28.6 | 89.6 | 45.7 | 21.2 | 14.2 | 18.2 |
4o | 100 | 100 | 94.6 | 100 | 38.7 | 26.1 | 71.2 | 25.4 |
4p | 100 | 100 | 100 | 100 | 100 | 42.0 | 37.2 | 80.9 |
Monosulfuron | 100 | 100 | 100 | 100 | 100 | 74.1 | 100 | 86.1 |
Chlorsulfuron | 100 | 100 | 100 | 100 | 96.3 | 73.1 | 100 | 22.7 |
Compd. | Brassica napus | Amaranthus retroflexus | Echinochloa crusgalli | Digitariasanguinalis | ||||
---|---|---|---|---|---|---|---|---|
Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | |
4a | 95.0 | 100 | 100 | 100 | 5.0 | |||
4b | 100 | 100 | 100 | 100 | 100 | 55.4 | 65.4 | 99 |
4c | 100 | 100 | 35.0 | 79.2 | 15.0 | |||
4d | 100 | 97.1 | 63.1 | 23.7 | ||||
4e | 100 | 93.7 | 20.0 | 31.8 | ||||
4f | 100 | 100 | 100 | 77.5 | ||||
4g | 100 | 100 | 100 | 100 | 100 | 55.4 | 48.3 | |
4h | 100 | 100 | 100 | 100 | 100 | 78.7 | 58.4 | |
4i | 100 | 60.5 | 85.7 | 63.4 | 20.8 | |||
4j | 95.1 | 80.1 | 70.0 | 77.9 | ||||
4k | 100 | 100 | 100 | 53.4 | 69.7 | 23.5 | ||
4l | 100 | 100 | 100 | 100 | 98.2 | |||
4m | 100 | 78.0 | 10.0 | 14.7 | 10.0 | |||
4n | 100 | 93.1 | 5.0 | 35.8 | ||||
4o | 100 | 85.4 | 65.7 | 81.0 | 30.2 | |||
4p | 100 | 100 | 100 | 99.0 | 98.6 | 56.6 | ||
Monosulfuron | 100 | 100 | 100 | 100 | 100 | 74.1 | 100 | 86.1 |
Chlorsulfuron | 100 | 100 | 100 | 100 | 96.3 | 73.1 | 100 | 22.7 |
Table 4 Herbicidal activities(%) of compounds 4a—4p by pot-culture method(75 g/ha)*
Compd. | Brassica napus | Amaranthus retroflexus | Echinochloa crusgalli | Digitariasanguinalis | ||||
---|---|---|---|---|---|---|---|---|
Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | Soil treatment | Foliage spray | |
4a | 95.0 | 100 | 100 | 100 | 5.0 | |||
4b | 100 | 100 | 100 | 100 | 100 | 55.4 | 65.4 | 99 |
4c | 100 | 100 | 35.0 | 79.2 | 15.0 | |||
4d | 100 | 97.1 | 63.1 | 23.7 | ||||
4e | 100 | 93.7 | 20.0 | 31.8 | ||||
4f | 100 | 100 | 100 | 77.5 | ||||
4g | 100 | 100 | 100 | 100 | 100 | 55.4 | 48.3 | |
4h | 100 | 100 | 100 | 100 | 100 | 78.7 | 58.4 | |
4i | 100 | 60.5 | 85.7 | 63.4 | 20.8 | |||
4j | 95.1 | 80.1 | 70.0 | 77.9 | ||||
4k | 100 | 100 | 100 | 53.4 | 69.7 | 23.5 | ||
4l | 100 | 100 | 100 | 100 | 98.2 | |||
4m | 100 | 78.0 | 10.0 | 14.7 | 10.0 | |||
4n | 100 | 93.1 | 5.0 | 35.8 | ||||
4o | 100 | 85.4 | 65.7 | 81.0 | 30.2 | |||
4p | 100 | 100 | 100 | 99.0 | 98.6 | 56.6 | ||
Monosulfuron | 100 | 100 | 100 | 100 | 100 | 74.1 | 100 | 86.1 |
Chlorsulfuron | 100 | 100 | 100 | 100 | 96.3 | 73.1 | 100 | 22.7 |
Compd. | Inhibition(%) | ||||||
---|---|---|---|---|---|---|---|
C. arachidicola | P. piricola | S. sclerotiorum | P. capsici | R. cerealis | C. lagenarium | B. cinerea | |
4a | 0.0 | 31.8 | 31.3 | 40.6 | 66.7 | 45.0 | 50.0 |
4b | 0.0 | 13.6 | 35.9 | 46.9 | 71.4 | 35.0 | 26.5 |
4c | 0.0 | 22.7 | 28.1 | 46.9 | 71.4 | 40.0 | 50.0 |
4d | 60.0 | 50.8 | 47.8 | 18.8 | 67.5 | 40.0 | 50.0 |
4e | 0 | 0 | 7.8 | 37.5 | 66.7 | 40.0 | 29.4 |
4f | 12.5 | 4.5 | 0 | 40.6 | 59.5 | 30.0 | 26.5 |
4g | 0.0 | 18.2 | 43.8 | 50.0 | 71.4 | 35.0 | 50.0 |
4h | 25.0 | 45.5 | 75.0 | 43.8 | 71.4 | 35.0 | 52.9 |
4i | 36.7 | 32.8 | 10.9 | 21.9 | 71.3 | 32.5 | 11.4 |
4j | 12.5 | 0.0 | 18.8 | 46.9 | 66.7 | 30.0 | 52.9 |
4k | 25.0 | 27.3 | 34.4 | 40.6 | 61.9 | 55.0 | 58.8 |
4l | 0 | 31.8 | 81.3 | 46.9 | 71.4 | 50.0 | 61.8 |
4m | 0.0 | 8.2 | 21.7 | 15.6 | 8.8 | 15.0 | 18.2 |
4n | 25.0 | 9.1 | 42.2 | 43.8 | 66.7 | 45.0 | 29.4 |
4o | 0.0 | 22.7 | 28.1 | 46.9 | 61.9 | 35.0 | 35.3 |
4p | 36.7 | 23.0 | 19.6 | 15.6 | 36.3 | 22.5 | 11.4 |
Chlorothalonil | 75.0 | <50.0 | <50.0 | 100 | 100 | 95.0 | 100 |
Carbendazim | <50.0 | 100 | 99.2 | <50.0 | 100 | 100 | <50.0 |
Table 5 Fungicidal activities of compounds 4a—4p at the dosage of 50 mg/L in vitro
Compd. | Inhibition(%) | ||||||
---|---|---|---|---|---|---|---|
C. arachidicola | P. piricola | S. sclerotiorum | P. capsici | R. cerealis | C. lagenarium | B. cinerea | |
4a | 0.0 | 31.8 | 31.3 | 40.6 | 66.7 | 45.0 | 50.0 |
4b | 0.0 | 13.6 | 35.9 | 46.9 | 71.4 | 35.0 | 26.5 |
4c | 0.0 | 22.7 | 28.1 | 46.9 | 71.4 | 40.0 | 50.0 |
4d | 60.0 | 50.8 | 47.8 | 18.8 | 67.5 | 40.0 | 50.0 |
4e | 0 | 0 | 7.8 | 37.5 | 66.7 | 40.0 | 29.4 |
4f | 12.5 | 4.5 | 0 | 40.6 | 59.5 | 30.0 | 26.5 |
4g | 0.0 | 18.2 | 43.8 | 50.0 | 71.4 | 35.0 | 50.0 |
4h | 25.0 | 45.5 | 75.0 | 43.8 | 71.4 | 35.0 | 52.9 |
4i | 36.7 | 32.8 | 10.9 | 21.9 | 71.3 | 32.5 | 11.4 |
4j | 12.5 | 0.0 | 18.8 | 46.9 | 66.7 | 30.0 | 52.9 |
4k | 25.0 | 27.3 | 34.4 | 40.6 | 61.9 | 55.0 | 58.8 |
4l | 0 | 31.8 | 81.3 | 46.9 | 71.4 | 50.0 | 61.8 |
4m | 0.0 | 8.2 | 21.7 | 15.6 | 8.8 | 15.0 | 18.2 |
4n | 25.0 | 9.1 | 42.2 | 43.8 | 66.7 | 45.0 | 29.4 |
4o | 0.0 | 22.7 | 28.1 | 46.9 | 61.9 | 35.0 | 35.3 |
4p | 36.7 | 23.0 | 19.6 | 15.6 | 36.3 | 22.5 | 11.4 |
Chlorothalonil | 75.0 | <50.0 | <50.0 | 100 | 100 | 95.0 | 100 |
Carbendazim | <50.0 | 100 | 99.2 | <50.0 | 100 | 100 | <50.0 |
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