高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (8): 1703.doi: 10.7503/cjcu20131258
杨冬燕1, 王蕾1, 贾长青1, 李长胜3, 马永强1(), 芮昌辉2, 徐彦军1, 覃兆海1
收稿日期:
2013-12-23
出版日期:
2014-08-10
发布日期:
2019-08-01
作者简介:
联系人简介: 马永强, 男, 博士, 教授, 博士生导师, 主要从事新农药创制研究. E-mail: 基金资助:
YANG Dongyan1, WANG Lei1, JIA Changqing1, LI Changsheng3, MA Yongqiang1,*(), RUI Changhui2, XU Yanjun1, QIN Zhaohai1,*
Received:
2013-12-23
Online:
2014-08-10
Published:
2019-08-01
Contact:
MA Yongqiang,QIN Zhaohai
E-mail:myqliang@iccas.ac.cn
Supported by:
摘要:
依据活性亚结构拼接原理, 以硝基胍为原料, 合成了一系列具有新烟碱类和缩氨基脲类杀虫剂共同结构特征的芳亚甲基硝基缩氨基胍类化合物, 其结构通过1H NMR、 IR和元素分析等方法进行了确证. 杀虫活性测定结果表明, 在600 μg/mL浓度下, 目标化合物对桃蚜[Myzuspersicae(Sulzer)]具有较优异的活性, 其中化合物4-2, 4-8, 4-10, 4-16, 4-27, 4-31和4-34的校正死亡率均在90%以上. 进一步以桃蚜、 棉蚜(Aphis gossypii)和桃粉蚜(Hyalopterusamygdali blanchard)为对象, 测定了化合物4-2, 4-8和4-34的精密毒力. 结果表明, 它们在低浓度下仍然具有很高的活性, 其中化合物4-8对棉蚜的活性甚至优于对照药剂吡虫啉, 在3.13 μg/mL浓度下致死率仍高达95.7%(吡虫啉为79.4%), 具有进一步研究开发的价值.
中图分类号:
TrendMD:
杨冬燕, 王蕾, 贾长青, 李长胜, 马永强, 芮昌辉, 徐彦军, 覃兆海. 芳亚甲基硝基缩氨基胍类化合物的合成及杀虫活性. 高等学校化学学报, 2014, 35(8): 1703.
YANG Dongyan, WANG Lei, JIA Changqing, LI Changsheng, MA Yongqiang, RUI Changhui, XU Yanjun, QIN Zhaohai. Syntheses and Insecticidal Activities of Nitro Arylideneamino Guanidine Derivatives†. Chem. J. Chinese Universities, 2014, 35(8): 1703.
Compd. | R' | R″ | m. p./℃ | Yield(%) | Elemental analysis(%, calcd.) | ||
---|---|---|---|---|---|---|---|
C | H | N | |||||
4-1 | C2H5 | H | 191—192 | 80 | 52.92(53.00) | 6.07(6.07) | 28.06(28.09) |
4-2 | n-C3H7 | H | 197—198 | 75 | 54.75(54.74) | 6.37(6.51) | 26.58(26.60) |
4-3 | Ph | H | 209—210 | 78 | 60.61(60.60) | 5.05(5.09) | 23.53(23.55) |
4-4 | CH2 | H | 141—142 | 61 | 53.42(53.44) | 5.23(5.30) | 28.27(28.32) |
4-5 | C2H5 | 2-Cl | 193—194 | 66 | 46.66(46.57) | 4.98(4.97) | 24.74(24.68) |
4-6 | n-C3H7 | 2-Cl | 195—196 | 78 | 48.52(48.41) | 5.40(5.42) | 23.65(23.52) |
4-7 | Ph | 2-Cl | 203—204 | 86 | 53.76(54.31) | 4.37(4.25) | 20.95(21.11) |
4-8 | CH2 | 2-Cl | 184—185 | 73 | 46.91(46.90) | 4.39(4.29) | 24.92(24.86) |
4-9 | CH≡≡C | 2-Cl | 203—204 | 65 | 47.44(47.24) | 3.56(3.60) | 24.87(25.04) |
4-10 | CH3 | 4-Me2N | 167—168 | 76 | 51.31(51.79) | 6.53(6.52) | 30.05(30.20) |
4-11 | C2H5 | 4-Me2N | 177—178 | 61 | 53.93(53.43) | 6.88(6.90) | 28.08(28.55) |
4-12 | Ph | 4-Me2N | 196—198 | 66 | 59.97(59.99) | 5.92(5.92) | 24.70(24.69) |
4-13 | CH2 | 4-Me2N | 179—180 | 76 | 52.18(52.65) | 6.35(6.25) | 28.29(28.79) |
4-14 | C2H5 | 2-MeO | 169—170 | 71 | 51.59(51.61) | 6.05(6.14) | 25.12(25.07) |
4-15 | n-C3H7 | 2-MeO | 188—189 | 64 | 53.36(53.23) | 6.56(6.53) | 23.94(23.88) |
4-16 | Ph | 2-MeO | 177—178 | 71 | 58.75(58.71) | 5.18(5.23) | 21.37(21.39) |
4-17 | CH2 | 2-MeO | 141—142 | 80 | 51.77(51.98) | 5.64(5.45) | 25.37(25.26) |
4-18 | CH≡≡C | 2-MeO | 180—181 | 74 | 52.41(52.36) | 4.63(4.76) | 25.33(25.44) |
4-19 | 2-Cl-Py-5-yl | 2-MeO | 203—204 | 71 | 49.70(49.66) | 4.08(4.17) | 22.83(23.17) |
4-20 | C2H5 | 2-NO2 | 158—159 | 57 | 44.90(44.90) | 4.73(4.80) | 28.51(28.56) |
4-21 | CH2 | 2-NO2 | 163—164 | 68 | 45.55(45.21) | 4.13(4.14) | 28.44(28.76) |
4-22 | C2H5 | 4-F | 198—199 | 82 | 49.33(49.44) | 5.27(5.28) | 26.30(26.20) |
4-23 | CH2 | 4-F | 186—187 | 67 | 48.98(48.81) | 4.48(4.56) | 25.81(26.30) |
4-24 | CH≡≡C | 4-F | 219—220 | 79 | 50.05(50.19) | 3.71(3.83) | 26.52(26.61) |
4-25 | CH3 | 4-CH3 | 176—177 | 68 | 52.81(53.00) | 6.03(6.07) | 27.95(28.09) |
4-26 | C2H5 | 4-CH3 | 174—175 | 76 | 54.88(54.74) | 6.47(6.51) | 26.81(26.60) |
4-27 | n-C3H7 | 4-CH3 | 173—174 | 77 | 56.39(56.30) | 6.87(6.91) | 25.53(25.25) |
4-28 | CH2=CH | 4-CH3 | 169—170 | 83 | 54.92(55.16) | 5.72(5.79) | 26.97(26.80) |
4-29 | CH≡≡C | 4-CH3 | 185—186 | 84 | 56.04(55.59) | 4.98(5.05) | 26.99(27.01) |
4-30 | 2-Cl-Py-5-yl | 4-CH3 | 196—197 | 67 | 51.98(51.95) | 4.31(4.36) | 24.04(24.23) |
4-31b | 2-Cl-Py-5-yl | H | 201—202 | 76 | 50.30(50.53) | 3.92(3.91) | 24.78(25.24) |
4-32b | 2-Cl-Py-5-yl | 2-Cl | 217—218 | 65 | 45.88(45.79) | 3.47(3.27) | 22.60(22.88) |
4-33b | 2-Cl-Py-5-yl | 4-MeO | 197—198 | 68 | 49.31(49.66) | 4.17(4.13) | 22.66(23.16) |
4-34b | 2-Cl-Py-5-yl | 2-NO2 | 228—229 | 73 | 44.63(44.51) | 3.37(3.18) | 25.46(25.94) |
4-35b | 2-Cl-Py-5-yl | 4-F | 202—203 | 86 | 47.38(47.94) | 3.37(3.42) | 23.31(23.95) |
Table 1 Physico-chemical data of compounds 4a
Compd. | R' | R″ | m. p./℃ | Yield(%) | Elemental analysis(%, calcd.) | ||
---|---|---|---|---|---|---|---|
C | H | N | |||||
4-1 | C2H5 | H | 191—192 | 80 | 52.92(53.00) | 6.07(6.07) | 28.06(28.09) |
4-2 | n-C3H7 | H | 197—198 | 75 | 54.75(54.74) | 6.37(6.51) | 26.58(26.60) |
4-3 | Ph | H | 209—210 | 78 | 60.61(60.60) | 5.05(5.09) | 23.53(23.55) |
4-4 | CH2 | H | 141—142 | 61 | 53.42(53.44) | 5.23(5.30) | 28.27(28.32) |
4-5 | C2H5 | 2-Cl | 193—194 | 66 | 46.66(46.57) | 4.98(4.97) | 24.74(24.68) |
4-6 | n-C3H7 | 2-Cl | 195—196 | 78 | 48.52(48.41) | 5.40(5.42) | 23.65(23.52) |
4-7 | Ph | 2-Cl | 203—204 | 86 | 53.76(54.31) | 4.37(4.25) | 20.95(21.11) |
4-8 | CH2 | 2-Cl | 184—185 | 73 | 46.91(46.90) | 4.39(4.29) | 24.92(24.86) |
4-9 | CH≡≡C | 2-Cl | 203—204 | 65 | 47.44(47.24) | 3.56(3.60) | 24.87(25.04) |
4-10 | CH3 | 4-Me2N | 167—168 | 76 | 51.31(51.79) | 6.53(6.52) | 30.05(30.20) |
4-11 | C2H5 | 4-Me2N | 177—178 | 61 | 53.93(53.43) | 6.88(6.90) | 28.08(28.55) |
4-12 | Ph | 4-Me2N | 196—198 | 66 | 59.97(59.99) | 5.92(5.92) | 24.70(24.69) |
4-13 | CH2 | 4-Me2N | 179—180 | 76 | 52.18(52.65) | 6.35(6.25) | 28.29(28.79) |
4-14 | C2H5 | 2-MeO | 169—170 | 71 | 51.59(51.61) | 6.05(6.14) | 25.12(25.07) |
4-15 | n-C3H7 | 2-MeO | 188—189 | 64 | 53.36(53.23) | 6.56(6.53) | 23.94(23.88) |
4-16 | Ph | 2-MeO | 177—178 | 71 | 58.75(58.71) | 5.18(5.23) | 21.37(21.39) |
4-17 | CH2 | 2-MeO | 141—142 | 80 | 51.77(51.98) | 5.64(5.45) | 25.37(25.26) |
4-18 | CH≡≡C | 2-MeO | 180—181 | 74 | 52.41(52.36) | 4.63(4.76) | 25.33(25.44) |
4-19 | 2-Cl-Py-5-yl | 2-MeO | 203—204 | 71 | 49.70(49.66) | 4.08(4.17) | 22.83(23.17) |
4-20 | C2H5 | 2-NO2 | 158—159 | 57 | 44.90(44.90) | 4.73(4.80) | 28.51(28.56) |
4-21 | CH2 | 2-NO2 | 163—164 | 68 | 45.55(45.21) | 4.13(4.14) | 28.44(28.76) |
4-22 | C2H5 | 4-F | 198—199 | 82 | 49.33(49.44) | 5.27(5.28) | 26.30(26.20) |
4-23 | CH2 | 4-F | 186—187 | 67 | 48.98(48.81) | 4.48(4.56) | 25.81(26.30) |
4-24 | CH≡≡C | 4-F | 219—220 | 79 | 50.05(50.19) | 3.71(3.83) | 26.52(26.61) |
4-25 | CH3 | 4-CH3 | 176—177 | 68 | 52.81(53.00) | 6.03(6.07) | 27.95(28.09) |
4-26 | C2H5 | 4-CH3 | 174—175 | 76 | 54.88(54.74) | 6.47(6.51) | 26.81(26.60) |
4-27 | n-C3H7 | 4-CH3 | 173—174 | 77 | 56.39(56.30) | 6.87(6.91) | 25.53(25.25) |
4-28 | CH2=CH | 4-CH3 | 169—170 | 83 | 54.92(55.16) | 5.72(5.79) | 26.97(26.80) |
4-29 | CH≡≡C | 4-CH3 | 185—186 | 84 | 56.04(55.59) | 4.98(5.05) | 26.99(27.01) |
4-30 | 2-Cl-Py-5-yl | 4-CH3 | 196—197 | 67 | 51.98(51.95) | 4.31(4.36) | 24.04(24.23) |
4-31b | 2-Cl-Py-5-yl | H | 201—202 | 76 | 50.30(50.53) | 3.92(3.91) | 24.78(25.24) |
4-32b | 2-Cl-Py-5-yl | 2-Cl | 217—218 | 65 | 45.88(45.79) | 3.47(3.27) | 22.60(22.88) |
4-33b | 2-Cl-Py-5-yl | 4-MeO | 197—198 | 68 | 49.31(49.66) | 4.17(4.13) | 22.66(23.16) |
4-34b | 2-Cl-Py-5-yl | 2-NO2 | 228—229 | 73 | 44.63(44.51) | 3.37(3.18) | 25.46(25.94) |
4-35b | 2-Cl-Py-5-yl | 4-F | 202—203 | 86 | 47.38(47.94) | 3.37(3.42) | 23.31(23.95) |
Compd. | 1H NMR(300 MHz, DMSO-d6), δ | IR(KBr), |
---|---|---|
4-1 | 0.91(t, J=7.40 Hz, 3H), 1.50—1.62(m, 2H), 4.03(t, J=7.60 Hz, 2H), 7.42—7.50(m, 3H), 7.98—8.04(m, 2H), 8.21(s, 1H), 8.79(brs, 2H) | 3423, 3300, 2931, 2873, 1594, 1527, 1414, 1355, 1253, 1184, 945, 761, 717 |
4-2 | 0.92(t, J=7.26 Hz, 3H), 1.27—1.40(m, 2H), 1.47—1.57(m, 2H), 4.07(t, J=7.41 Hz, 2H), 7.43—7.48(m, 3H), 7.98—8.03(m, 2H), 8.19(s, 1H), 8.78(brs, 2H) | 3422, 3300, 2930, 2864, 1594, 1527, 1450, 1411, 1376, 1243, 1036, 975, 760, 695 |
4-3 | 5.40(s, 2H), 7.23—7.29(m, 3H), 7.34—7.43(m, 5H), 7.87—7.90(m, 2H), 8.04(s, 1H), 9.01(brs, 2H) | 3423, 3301, 1595, 1525, 1417, 1367, 1253, 1056, 942, 760, 691 |
4-4 | 4.79—4.82(m, 2H), 5.10—5.17(m, 1H), 5.25—5.30(m, 1H), 5.76—5.85(m, 1H), 7.43—7.47(m, 3H), 7.66—7.70(m, 3H), 7.84(s, 1H), 9.17(brs, 1H) | 3428, 3298, 1645, 1596, 1522, 1416, 1245, 1134, 1045, 939, 918, 752 |
4-5 | 0.92(t, J=7.43 Hz, 3H), 1.53—1.65(m, 2H), 4.07(t, J=7.52 Hz, 2H), 7.40—7.57(m, 3H), 8.28(s, 1H), 8.38—8.42(m, 1H), 8.86(brs, 2H) | 3420, 3302, 2939, 2878, 1595, 1525, 1416, 1356, 1242, 1035, 764 |
4-6 | 0.94(t, J=7.28 Hz, 3H), 1.29—1.41(m, 2H), 1.49—1.59(m, 2H), 4.11(t, J=7.47 Hz, 2H), 7.40—7.51(m, 2H), 7.54—7.57(m, 1H), 8.28(s, 1H), 8.40—8.43(m, 1H), 8.87(brs, 2H) | 3427, 3309, 2930, 2868, 1592, 1524, 1411, 1241, 1031, 930, 763 |
4-7 | 5.42(s, 2H), 7.25—7.31(m, 2H), 7.36—7.47(m, 5H), 8.17(s, 1H), 8.41—8.44(m, 2H), 9.08(brs, 2H) | 3442, 3328, 1589, 1521, 1476, 1412, 1370, 1239, 1044, 947, 760, 701 |
4-8 | 4.80(t, J=2.24 Hz, 2H), 5.09(q, J=6.18 Hz, 1H), 5.26(q, J=3.90 Hz, 1H), 5.76—5.88(m, 1H), 7.40—7.55(m, 3H), 8.20(s, 1H), 8.43(q, J=3.16 Hz, 1H), 8.96(brs, 2H) | 3441, 3324, 1593, 1524, 1477, 1413, 1365, 1245, 1042, 939, 760 |
4-9 | 3.48(t, J=2.37 Hz, 1H), 5.02(d, J=2.31 Hz, 2H), 7.42— 7.59(m, 3H), 8.42(s, 1H), 8.42—8.50(m, 1H), 9.02(brs, 2H) | 3424, 3273, 2360, 2127, 1597, 1522, 1425, 1369, 1238, 1138, 1046, 924, 763, 681 |
4-10 | 1.10(t, J=6.98 Hz, 3H), 2.99(s, 6H), 4.08(q, J=6.97 Hz, 2H), 6.74(d, J=8.97 Hz, 2H), 7.79(d, J=8.91 Hz, 2H), 8.09(s, 1H), 8.65(brs, 2H) | 3448, 3335, 2927, 2356, 1589, 1520, 1430, 1363, 1240, 1185, 1018, 941, 818 |
4-11 | 0.89(t, J=7.38 Hz, 3H), 1.47—1.60(m, 2H), 2.99(s, 6H), 3.99(t, J=7.56 Hz, 2H), 6.74(d, J=8.97 Hz, 2H), 7.80(d, J=8.91 Hz, 2H), 8.07(s, 1H), 8.67(brs, 2H) | 3422, 3310, 2930, 2359, 1591, 1524, 1368, 1235, 1185, 1031, 944, 816 |
4-12 | 2.95(s, 6H), 5.36(s, 2H), 6.68(d, J=9.00 Hz, 2H), 7.21—7.28(m, 3H), 7.33—7.38(m, 2H), 7.67(d, J=8.97 Hz, 2H), 7.91(s, 1H), 8.87(brs, 2H) | 3441, 3303, 2800, 2184, 1592, 1520, 1398, 1249, 1048, 944, 821 |
4-13 | 2.98(s, 6H), 4.72(t, J=2.1 Hz, 2H), 5.03(q, J=6.23 Hz, 1H), 5.17(q, J=3.94 Hz, 1H), 5.76—5.88(m, 1H), 6.71(t, J=5.85 Hz, 2H), 7.74(t, J=5.79 Hz, 2H), 7.91(s, 1H), 8.79(brs, 2H) | 3416, 3304, 2901, 1901, 1610, 1526, 1411, 1366, 1248, 1183, 1046, 942, 819 |
4-14 | 0.90(t, J=7.43 Hz, 3H), 1.49—1.62(m, 2H), 3.88(s, 3H), 4.02(t, J=7.49 Hz, 2H), 7.02(t, J=7.50 Hz, 1H), 7.11— 7.14(m, 1H), 7.42—7.48(m, 1H), 8.21—8.24(m, 1H), 8.29(s, 1H), 8.80(brs, 2H) | 3435, 3298, 2960, 2048, 1797, 1038, 942, 751 |
4-15 | 0.94(t, J=7.28 Hz, 3H), 1.27—1.39(m, 2H), 1.46—1.56(m, 2H), 3.88(s, 3H), 4.06(t, J=7.39 Hz, 2H), 7.11— 7.14(m, 1H), 7.42—7.48(m, 1H), 8.17—8.24(m, 1H), 8.30(s, 1H), 8.78(brs, 2H) | 3429, 3310, 2961, 2873, 1595, 1526, 1490, 1413, 1359, 1239, 1034, 931, 761 |
4-16 | 3.72(s, 3H), 5.37(s, 2H), 6.96—7.05(m, 2H), 7.23— 7.30(m, 3H), 7.32—7.43(m, 3H), 8.22(s, 1H), 8.23(d, J=3.84 Hz, 1H), 8.99(brs, 2H) | 3424, 3310, 2958, 2835, 1601, 1520, 1044, 936, 745 |
4-17 | 3.89(s, 3H), 4.79—4.82(m, 2H), 5.12—5.29(m, 2H), 5.74—5.86(m, 1H), 6.94—7.04(m, 2H), 7.39—7.45(m, 1H), 7.64(brs, 1H), 7.80—7.83(m, 1H), 8.29(s, 1H), 9.16(brs, 1H) | 3445, 3330, 1606, 1566, 1401, 1239, 1136, 1045, 948, 754 |
4-18 | 3.42(s, 1H), 3.89(s,3H), 4.94(s, 2H), 7.01—7.06(m, 1H), 7.11—7.15(m, 1H), 7.43—7.49(m, 1H), 8.27—8.30(m, 1H), 8.41(s, 1H), 8.92(brs, 2H) | 3416, 3308, 2989, 2117, 1609, 1223, 1059, 942, 751 |
4-19 | 3.84(d, J=8.25 Hz, 3H), 5.41(s,2H), 6.91(t, J=4.19 Hz, 1H), 6.99(t, J=7.56 Hz, 1H), 7.31—7.34(m, 1H), 7.38—7.44(m, 1H), 7.60—7.78(m, 2H), 7.70(brs, 1H), 8.28(s, 1H), 8.38(t, J=1.26 Hz, 1H), 9.23(brs, 1H) | 3460, 3345, 3049, 2842, 1597, 1517, 1463, 1367, 1231, 1106, 1021, 921, 814, 749 |
4-20 | 0.85—0.97(m, 3H), 1.55—1.67(m, 2H), 4.00(t, J=7.58 Hz, 2H), 7.67—7.73(m, 1H), 7.79—7.85(m, 1H), 8.10(q, J=3.09 Hz, 1H), 8.41(s, 1H), 8.42(q, J=2.57 Hz, 1H), 8.86(brs, 2H) | 3461, 3354, 2962, 2876, 1584, 1241, 1022, 944, 853, 786, 743 |
4-21 | 4.72(t, J=2.22 Hz, 2H), 5.08(q, J=6.17 Hz, 1H), 5.26(q, J=3.89 Hz, 1H), 5.89—5.76(m, 1H), 7.67—7.72(m, 1H), 7.78—7.84(m, 1H), 8.06—8.09(m, 1H), 8.32(s, 1H), 8.48(m, 1H), 8.95(brs, 2H) | 3430, 3327, 1606, 1519, 1049, 940, 844, 789, 736, 686 |
4-22 | 0.90(t, J=7.38 Hz, 3H), 1.49—1.59(m, 2H), 4.01(t, J=7.62 Hz, 2H), 7.27—7.34(m, 2H), 8.07—8.13(m, 2H), 8.21(s, 1H), 8.84(brs, 2H) | 3417, 3299, 2927, 2852, 1595, 1223, 1035, 945, 868, 838, 718 |
4-23 | 4.74(t, J=2.06 Hz, 2H), 5.03(q, J=6.20 Hz, 1H), 5.19(q, J=3.93 Hz, 1H), 5.76—5.88(m, 1H), 7.26—7.34(m, 2H), 8.03—8.09(m, 2H), 8.06(s, 1H), 8.94(brs, 2H) | 3430, 3298, 1601, 1508, 1421, 1229, 1134, 1044, 940, 919, 832 |
4-24 | 3.34—3.40(m, 1H), 4.94(d, J=2.22 Hz, 2H), 7.29—7.36(m, 2H), 8.09—8.14(m, 2H), 8.23(s, 1H), 8.99(brs, 2H) | 3440, 3304, 2121, 1600, 1510, 1420, 1370, 1231, 1131, 1047, 955, 843 |
4-25 | 1.25(t, J=7.11 Hz, 3H), 2.42(s, 3H), 4.19(q, J=7.12 Hz, 2H), 7.26(t, J=3.93 Hz, 3H) , 7.58(d, J=8.25 Hz, 2H), 7.86(s, 1H), 9.11(brs, 1H) | 3438, 3327, 2969, 1607, 1522, 1485, 1413, 1368, 1316, 1246, 1185, 1017 |
4-26 | 1.02(t, J=5.40 Hz, 3H), 1.60—1.71(m, 2H), 2.41(s, 3H), 4.08(t, J=7.74 Hz, 2H), 7.26(t, J=4.01 Hz, 2H), 7.57(t, J=8.81 Hz, 3H), 7.82(s, 1H), 9.09(brs, 1H) | 3416, 3299, 2959, 2875, 1595, 1530, 1405, 1243, 1031, 933, 812 |
4-27 | 0.97(t, J=7.26 Hz, 3H), 1.35—1.48(m, 2H), 1.56—1.66(m, 2H), 2.41(s, 3H), 4.11(t, J=7.61 Hz, 2H), 7.26(t, J=3.96 Hz, 2H), 7.57(t, J=9.29 Hz, 3H), 7.84(s, 1H) , 9.09(brs, 1H) | 3416, 3310, 2959, 2865, 1597, 1459, 1041, 931, 818 |
4-28 | 2.41(s, 3H), 4.78—4.81(m, 2H), 5.09—5.16(m, 1H), 5.24—5.29(m, 1H), 5.74—5.85(m, 1H), 7.25(d, J=8.71 Hz, 2H), 7.56(q, J=6.58 Hz, 3H), 7.81(s, 1H), 9.17(brs, 1H) | 3424, 3314, 1613, 1524, 1470, 1360, 1188, 1050, 936 |
4-29 | 2.42(s, 3H), 4.52—4.64(m, 1H), 4.96(d, J=2.40 Hz, 2H), 7.27(d, J=6.15 Hz, 2H), 7.61(d, J=8.25 Hz, 3H), 8.05(s, 1H), 9.16(brs, 1H) | 3444, 3326, 2118, 1598, 1522, 1434, 1046, 928, 816 |
4-30 | 2.33(s, 3H), 5.40(s, 2H), 7.23(d, J=7.91 Hz, 2H), 7.50(t, J=4.14 Hz, 1H), 7.68(q, J=5.74 Hz, 1H), 7.82(d, J=8.15 Hz, 2H), 8.06(s, 1H), 8.38(d, J=2.50 Hz, 1H), 9.00(brs,2H) | 3435, 3314, 3044, 1608, 1480, 1429, 1366, 1243, 1094, 1052, 939, 819 |
Table 2 1H NMR and IR data of compounds 4
Compd. | 1H NMR(300 MHz, DMSO-d6), δ | IR(KBr), |
---|---|---|
4-1 | 0.91(t, J=7.40 Hz, 3H), 1.50—1.62(m, 2H), 4.03(t, J=7.60 Hz, 2H), 7.42—7.50(m, 3H), 7.98—8.04(m, 2H), 8.21(s, 1H), 8.79(brs, 2H) | 3423, 3300, 2931, 2873, 1594, 1527, 1414, 1355, 1253, 1184, 945, 761, 717 |
4-2 | 0.92(t, J=7.26 Hz, 3H), 1.27—1.40(m, 2H), 1.47—1.57(m, 2H), 4.07(t, J=7.41 Hz, 2H), 7.43—7.48(m, 3H), 7.98—8.03(m, 2H), 8.19(s, 1H), 8.78(brs, 2H) | 3422, 3300, 2930, 2864, 1594, 1527, 1450, 1411, 1376, 1243, 1036, 975, 760, 695 |
4-3 | 5.40(s, 2H), 7.23—7.29(m, 3H), 7.34—7.43(m, 5H), 7.87—7.90(m, 2H), 8.04(s, 1H), 9.01(brs, 2H) | 3423, 3301, 1595, 1525, 1417, 1367, 1253, 1056, 942, 760, 691 |
4-4 | 4.79—4.82(m, 2H), 5.10—5.17(m, 1H), 5.25—5.30(m, 1H), 5.76—5.85(m, 1H), 7.43—7.47(m, 3H), 7.66—7.70(m, 3H), 7.84(s, 1H), 9.17(brs, 1H) | 3428, 3298, 1645, 1596, 1522, 1416, 1245, 1134, 1045, 939, 918, 752 |
4-5 | 0.92(t, J=7.43 Hz, 3H), 1.53—1.65(m, 2H), 4.07(t, J=7.52 Hz, 2H), 7.40—7.57(m, 3H), 8.28(s, 1H), 8.38—8.42(m, 1H), 8.86(brs, 2H) | 3420, 3302, 2939, 2878, 1595, 1525, 1416, 1356, 1242, 1035, 764 |
4-6 | 0.94(t, J=7.28 Hz, 3H), 1.29—1.41(m, 2H), 1.49—1.59(m, 2H), 4.11(t, J=7.47 Hz, 2H), 7.40—7.51(m, 2H), 7.54—7.57(m, 1H), 8.28(s, 1H), 8.40—8.43(m, 1H), 8.87(brs, 2H) | 3427, 3309, 2930, 2868, 1592, 1524, 1411, 1241, 1031, 930, 763 |
4-7 | 5.42(s, 2H), 7.25—7.31(m, 2H), 7.36—7.47(m, 5H), 8.17(s, 1H), 8.41—8.44(m, 2H), 9.08(brs, 2H) | 3442, 3328, 1589, 1521, 1476, 1412, 1370, 1239, 1044, 947, 760, 701 |
4-8 | 4.80(t, J=2.24 Hz, 2H), 5.09(q, J=6.18 Hz, 1H), 5.26(q, J=3.90 Hz, 1H), 5.76—5.88(m, 1H), 7.40—7.55(m, 3H), 8.20(s, 1H), 8.43(q, J=3.16 Hz, 1H), 8.96(brs, 2H) | 3441, 3324, 1593, 1524, 1477, 1413, 1365, 1245, 1042, 939, 760 |
4-9 | 3.48(t, J=2.37 Hz, 1H), 5.02(d, J=2.31 Hz, 2H), 7.42— 7.59(m, 3H), 8.42(s, 1H), 8.42—8.50(m, 1H), 9.02(brs, 2H) | 3424, 3273, 2360, 2127, 1597, 1522, 1425, 1369, 1238, 1138, 1046, 924, 763, 681 |
4-10 | 1.10(t, J=6.98 Hz, 3H), 2.99(s, 6H), 4.08(q, J=6.97 Hz, 2H), 6.74(d, J=8.97 Hz, 2H), 7.79(d, J=8.91 Hz, 2H), 8.09(s, 1H), 8.65(brs, 2H) | 3448, 3335, 2927, 2356, 1589, 1520, 1430, 1363, 1240, 1185, 1018, 941, 818 |
4-11 | 0.89(t, J=7.38 Hz, 3H), 1.47—1.60(m, 2H), 2.99(s, 6H), 3.99(t, J=7.56 Hz, 2H), 6.74(d, J=8.97 Hz, 2H), 7.80(d, J=8.91 Hz, 2H), 8.07(s, 1H), 8.67(brs, 2H) | 3422, 3310, 2930, 2359, 1591, 1524, 1368, 1235, 1185, 1031, 944, 816 |
4-12 | 2.95(s, 6H), 5.36(s, 2H), 6.68(d, J=9.00 Hz, 2H), 7.21—7.28(m, 3H), 7.33—7.38(m, 2H), 7.67(d, J=8.97 Hz, 2H), 7.91(s, 1H), 8.87(brs, 2H) | 3441, 3303, 2800, 2184, 1592, 1520, 1398, 1249, 1048, 944, 821 |
4-13 | 2.98(s, 6H), 4.72(t, J=2.1 Hz, 2H), 5.03(q, J=6.23 Hz, 1H), 5.17(q, J=3.94 Hz, 1H), 5.76—5.88(m, 1H), 6.71(t, J=5.85 Hz, 2H), 7.74(t, J=5.79 Hz, 2H), 7.91(s, 1H), 8.79(brs, 2H) | 3416, 3304, 2901, 1901, 1610, 1526, 1411, 1366, 1248, 1183, 1046, 942, 819 |
4-14 | 0.90(t, J=7.43 Hz, 3H), 1.49—1.62(m, 2H), 3.88(s, 3H), 4.02(t, J=7.49 Hz, 2H), 7.02(t, J=7.50 Hz, 1H), 7.11— 7.14(m, 1H), 7.42—7.48(m, 1H), 8.21—8.24(m, 1H), 8.29(s, 1H), 8.80(brs, 2H) | 3435, 3298, 2960, 2048, 1797, 1038, 942, 751 |
4-15 | 0.94(t, J=7.28 Hz, 3H), 1.27—1.39(m, 2H), 1.46—1.56(m, 2H), 3.88(s, 3H), 4.06(t, J=7.39 Hz, 2H), 7.11— 7.14(m, 1H), 7.42—7.48(m, 1H), 8.17—8.24(m, 1H), 8.30(s, 1H), 8.78(brs, 2H) | 3429, 3310, 2961, 2873, 1595, 1526, 1490, 1413, 1359, 1239, 1034, 931, 761 |
4-16 | 3.72(s, 3H), 5.37(s, 2H), 6.96—7.05(m, 2H), 7.23— 7.30(m, 3H), 7.32—7.43(m, 3H), 8.22(s, 1H), 8.23(d, J=3.84 Hz, 1H), 8.99(brs, 2H) | 3424, 3310, 2958, 2835, 1601, 1520, 1044, 936, 745 |
4-17 | 3.89(s, 3H), 4.79—4.82(m, 2H), 5.12—5.29(m, 2H), 5.74—5.86(m, 1H), 6.94—7.04(m, 2H), 7.39—7.45(m, 1H), 7.64(brs, 1H), 7.80—7.83(m, 1H), 8.29(s, 1H), 9.16(brs, 1H) | 3445, 3330, 1606, 1566, 1401, 1239, 1136, 1045, 948, 754 |
4-18 | 3.42(s, 1H), 3.89(s,3H), 4.94(s, 2H), 7.01—7.06(m, 1H), 7.11—7.15(m, 1H), 7.43—7.49(m, 1H), 8.27—8.30(m, 1H), 8.41(s, 1H), 8.92(brs, 2H) | 3416, 3308, 2989, 2117, 1609, 1223, 1059, 942, 751 |
4-19 | 3.84(d, J=8.25 Hz, 3H), 5.41(s,2H), 6.91(t, J=4.19 Hz, 1H), 6.99(t, J=7.56 Hz, 1H), 7.31—7.34(m, 1H), 7.38—7.44(m, 1H), 7.60—7.78(m, 2H), 7.70(brs, 1H), 8.28(s, 1H), 8.38(t, J=1.26 Hz, 1H), 9.23(brs, 1H) | 3460, 3345, 3049, 2842, 1597, 1517, 1463, 1367, 1231, 1106, 1021, 921, 814, 749 |
4-20 | 0.85—0.97(m, 3H), 1.55—1.67(m, 2H), 4.00(t, J=7.58 Hz, 2H), 7.67—7.73(m, 1H), 7.79—7.85(m, 1H), 8.10(q, J=3.09 Hz, 1H), 8.41(s, 1H), 8.42(q, J=2.57 Hz, 1H), 8.86(brs, 2H) | 3461, 3354, 2962, 2876, 1584, 1241, 1022, 944, 853, 786, 743 |
4-21 | 4.72(t, J=2.22 Hz, 2H), 5.08(q, J=6.17 Hz, 1H), 5.26(q, J=3.89 Hz, 1H), 5.89—5.76(m, 1H), 7.67—7.72(m, 1H), 7.78—7.84(m, 1H), 8.06—8.09(m, 1H), 8.32(s, 1H), 8.48(m, 1H), 8.95(brs, 2H) | 3430, 3327, 1606, 1519, 1049, 940, 844, 789, 736, 686 |
4-22 | 0.90(t, J=7.38 Hz, 3H), 1.49—1.59(m, 2H), 4.01(t, J=7.62 Hz, 2H), 7.27—7.34(m, 2H), 8.07—8.13(m, 2H), 8.21(s, 1H), 8.84(brs, 2H) | 3417, 3299, 2927, 2852, 1595, 1223, 1035, 945, 868, 838, 718 |
4-23 | 4.74(t, J=2.06 Hz, 2H), 5.03(q, J=6.20 Hz, 1H), 5.19(q, J=3.93 Hz, 1H), 5.76—5.88(m, 1H), 7.26—7.34(m, 2H), 8.03—8.09(m, 2H), 8.06(s, 1H), 8.94(brs, 2H) | 3430, 3298, 1601, 1508, 1421, 1229, 1134, 1044, 940, 919, 832 |
4-24 | 3.34—3.40(m, 1H), 4.94(d, J=2.22 Hz, 2H), 7.29—7.36(m, 2H), 8.09—8.14(m, 2H), 8.23(s, 1H), 8.99(brs, 2H) | 3440, 3304, 2121, 1600, 1510, 1420, 1370, 1231, 1131, 1047, 955, 843 |
4-25 | 1.25(t, J=7.11 Hz, 3H), 2.42(s, 3H), 4.19(q, J=7.12 Hz, 2H), 7.26(t, J=3.93 Hz, 3H) , 7.58(d, J=8.25 Hz, 2H), 7.86(s, 1H), 9.11(brs, 1H) | 3438, 3327, 2969, 1607, 1522, 1485, 1413, 1368, 1316, 1246, 1185, 1017 |
4-26 | 1.02(t, J=5.40 Hz, 3H), 1.60—1.71(m, 2H), 2.41(s, 3H), 4.08(t, J=7.74 Hz, 2H), 7.26(t, J=4.01 Hz, 2H), 7.57(t, J=8.81 Hz, 3H), 7.82(s, 1H), 9.09(brs, 1H) | 3416, 3299, 2959, 2875, 1595, 1530, 1405, 1243, 1031, 933, 812 |
4-27 | 0.97(t, J=7.26 Hz, 3H), 1.35—1.48(m, 2H), 1.56—1.66(m, 2H), 2.41(s, 3H), 4.11(t, J=7.61 Hz, 2H), 7.26(t, J=3.96 Hz, 2H), 7.57(t, J=9.29 Hz, 3H), 7.84(s, 1H) , 9.09(brs, 1H) | 3416, 3310, 2959, 2865, 1597, 1459, 1041, 931, 818 |
4-28 | 2.41(s, 3H), 4.78—4.81(m, 2H), 5.09—5.16(m, 1H), 5.24—5.29(m, 1H), 5.74—5.85(m, 1H), 7.25(d, J=8.71 Hz, 2H), 7.56(q, J=6.58 Hz, 3H), 7.81(s, 1H), 9.17(brs, 1H) | 3424, 3314, 1613, 1524, 1470, 1360, 1188, 1050, 936 |
4-29 | 2.42(s, 3H), 4.52—4.64(m, 1H), 4.96(d, J=2.40 Hz, 2H), 7.27(d, J=6.15 Hz, 2H), 7.61(d, J=8.25 Hz, 3H), 8.05(s, 1H), 9.16(brs, 1H) | 3444, 3326, 2118, 1598, 1522, 1434, 1046, 928, 816 |
4-30 | 2.33(s, 3H), 5.40(s, 2H), 7.23(d, J=7.91 Hz, 2H), 7.50(t, J=4.14 Hz, 1H), 7.68(q, J=5.74 Hz, 1H), 7.82(d, J=8.15 Hz, 2H), 8.06(s, 1H), 8.38(d, J=2.50 Hz, 1H), 9.00(brs,2H) | 3435, 3314, 3044, 1608, 1480, 1429, 1366, 1243, 1094, 1052, 939, 819 |
Compd. | Corrected death rate(%) | Compd. | Corrected death rate(%) | Compd. | Corrected death rate(%) |
---|---|---|---|---|---|
4-1 | 14.8 | 4-14 | 20.2 | 4-27 | 93.2 |
4-2 | 96.4 | 4-15 | 40.4 | 4-28 | 82.4 |
4-3 | 20.9 | 4-16 | 92.8 | 4-29 | 8.1 |
4-4 | 30.6 | 4-17 | 3.4 | 4-30 | 3.7 |
4-5 | 41.2 | 4-18 | 4.2 | 4-31 | 92.8 |
4-6 | 1.2 | 4-19 | 6.7 | 4-32 | 22.0 |
4-7 | 45.8 | 4-20 | 31.5 | 4-33 | 54.4 |
4-8 | 96.0 | 4-21 | 0 | 4-34 | 100 |
4-9 | 31.2 | 4-22 | 20.3 | 4-35 | 72.3 |
4-10 | 90.6 | 4-23 | 17.7 | CK | 7.7 |
4-11 | 0 | 4-24 | 31.6 | Imidacloprid | 100 |
4-12 | 0 | 4-25 | 86.0 | ||
4-13 | 23.6 | 4-26 | 7.7 |
Table 3 Insecticidal activities of target compounds against Myzuspersicae
Compd. | Corrected death rate(%) | Compd. | Corrected death rate(%) | Compd. | Corrected death rate(%) |
---|---|---|---|---|---|
4-1 | 14.8 | 4-14 | 20.2 | 4-27 | 93.2 |
4-2 | 96.4 | 4-15 | 40.4 | 4-28 | 82.4 |
4-3 | 20.9 | 4-16 | 92.8 | 4-29 | 8.1 |
4-4 | 30.6 | 4-17 | 3.4 | 4-30 | 3.7 |
4-5 | 41.2 | 4-18 | 4.2 | 4-31 | 92.8 |
4-6 | 1.2 | 4-19 | 6.7 | 4-32 | 22.0 |
4-7 | 45.8 | 4-20 | 31.5 | 4-33 | 54.4 |
4-8 | 96.0 | 4-21 | 0 | 4-34 | 100 |
4-9 | 31.2 | 4-22 | 20.3 | 4-35 | 72.3 |
4-10 | 90.6 | 4-23 | 17.7 | CK | 7.7 |
4-11 | 0 | 4-24 | 31.6 | Imidacloprid | 100 |
4-12 | 0 | 4-25 | 86.0 | ||
4-13 | 23.6 | 4-26 | 7.7 |
Insecticidal activity | Concentration/(μg·mL-1) | Death rate(%) | |||
---|---|---|---|---|---|
4-2 | 4-8 | 4-34 | Imidacloprid | ||
Myzuspersicae(24 h) | 400 | 100 | 100 | 95.5 | |
200 | 100 | 100 | 100 | ||
100 | 98.7 | 100 | 100 | ||
50 | 97.5 | 95.9 | 97.1 | 100 | |
25 | 66.7 | 100 | 60 | 100 | |
Hyalopterusamygdali blanchard(24 h) | 400 | 100 | 100 | 100 | |
200 | 100 | 100 | 100 | ||
100 | 96.5 | 100 | 98.1 | ||
50 | 93.1 | 96.3 | 96.4 | 100 | |
25 | 78.9 | 91.1 | 74.6 | 100 | |
Aphis gossypii(5 h) | 50 | 95.2 | 100 | 100 | 100 |
12.5 | 86.8 | 100 | 100 | 93.8 | |
3.13 | 76.2 | 95.7 | 86.0 | 79.4 |
Table 4 Insecticidal activities of compounds 4-2, 4-8 and 4-34
Insecticidal activity | Concentration/(μg·mL-1) | Death rate(%) | |||
---|---|---|---|---|---|
4-2 | 4-8 | 4-34 | Imidacloprid | ||
Myzuspersicae(24 h) | 400 | 100 | 100 | 95.5 | |
200 | 100 | 100 | 100 | ||
100 | 98.7 | 100 | 100 | ||
50 | 97.5 | 95.9 | 97.1 | 100 | |
25 | 66.7 | 100 | 60 | 100 | |
Hyalopterusamygdali blanchard(24 h) | 400 | 100 | 100 | 100 | |
200 | 100 | 100 | 100 | ||
100 | 96.5 | 100 | 98.1 | ||
50 | 93.1 | 96.3 | 96.4 | 100 | |
25 | 78.9 | 91.1 | 74.6 | 100 | |
Aphis gossypii(5 h) | 50 | 95.2 | 100 | 100 | 100 |
12.5 | 86.8 | 100 | 100 | 93.8 | |
3.13 | 76.2 | 95.7 | 86.0 | 79.4 |
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