Design, Synthesis and Biological Activity of Novel Aphid Alarm Pheromone Analogues Containing Isonicotinic Acid†

doi:10.7503/cjcu20160434

Abstract

Abstract:

A series of new aphid alarm pheromone[(E)-β-farnesene, EBF] analogues containing isonicotinic acid was designed based on the principles of connecting sub-structure and bioisosterism. With EBF as a lead compound, 20 EBF analogues were prepared via four steps starting from geraniol. Their structures were confirmed by ¹H NMR, ¹³C NMR, IR and HRMS. The preliminary bioassay suggested that all the analogues showed repellent and aphicidal activities against Myzus persicae(Sulzer). Among them, compounds 7d, 8f and 8n showed good repellent activity with the repellent rate of 62.6%, 62.0% and 61.0% respectively; and the analogues 8a, 8b and 8d exhibited better aphicidal mortality of 73.6%, 81.1% and 70.2% than lead EBF. The primary structure-activity relationship(SAR) analysis indicated that introducing of ester group was favorable to repellent activity while introducing amide was conducive to aphicidal activity. Moreover, N-substituted carbon chain length, number of branched chain as well as aromaticity played roles in repellent activity. This study provides useful clues for further development of novel aphid control agent.

Key words: Isonicotinic acid, Aphid alarm pheromone, Analogue, Biological activity

CLC Number:

O626

TrendMD:

QIN Yaoguo, ZHANG Jingpeng, SONG Dunlun, DUAN Hongxia, LING Yun, JIANG Biaobiao, WANG Di, YANG Xinling. Design, Synthesis and Biological Activity of Novel Aphid Alarm Pheromone Analogues Containing Isonicotinic Acid^†[J]. Chem. J. Chinese Universities, 2016, 37(11): 1977.

Figures/Tables 8

Fig.1 Structure of (E)-β-farnesene

Scheme 1 Design strategy(X), general synthetic route of intermediates(Y) and target compounds(Z)2a, 7a: R1=H, R2=H; 2b, 7b: R1=Cl, R2=Cl; 2c, 7c: R1=Cl, R2=OCH3; 2d, 7d: R1=Cl, R2=H; 2e, 7e: R1=OCH3, R2=H; 6a: R=CH3; 6b: R=CH2CH3; 6c: R=(CH2)2CH3; 6d: R =(CH2)3CH3; 6e: R=(CH2)4CH3; 6f: R=(CH2)5CH3; 6g: R=CH(CH3)2; 6h: R=CH2CH(CH3)2; 6i: R=C(CH3)3; 6j: R=A; 6k: R=B; 6l: R=C; 8a: R1=H, R2=H, R=H; 8b: R1=Cl, R2=Cl, R=H; 8c: R1=Cl, R2=OCH3, R=H; 8d: R1=Cl, R2=Cl, R=CH3; 8e: R1=Cl, R2=Cl, R=CH2CH3; 8f: R1=Cl, R2=Cl, R=(CH2)2CH3; 8g: R1=Cl, R2=Cl, R=(CH2)3CH3; 8h: R1=Cl, R2=Cl, R=(CH2)4CH3; 8i: R1=Cl, R2=Cl, R=(CH2)5CH3; 8j: R1=Cl, R2=Cl, R=CH(CH3)2; 8k: R1=Cl, R2=Cl, R=CH2CH(CH3)2; 8l: R1=Cl, R2=Cl, R=C(CH3)3; 8m: R1=Cl, R2=Cl, R=A; 8n: R1=Cl, R2=Cl, R=B; 8o: R1=Cl, R2=Cl, R=C. A= ; B=; C=.

Table 1 MS data of intermediates 4—6*

Compd.	Chemical formula	MS(calcd.), m/z	Compd.	Chemical formula	MS(calcd.), m/z
4	C₁₁H₂₀O	169.1(168.1)	6f	C₁₆H₃₁N	238.2(237.2)
5	C₁₀H₁₉N	154.2(153.2)	6g	C₁₃H₂₅N	196.2(195.2)
6a	C₁₁H₂₁N	168.2(167.2)	6h	C₁₄H₂₇N	210.2(209.2)
6b	C₁₂H₂₃N	182.2(181.2)	6i	C₁₄H₂₇N	210.2(209.2)
6c	C₁₃H₂₅N	196.2(195.2)	6j	C₁₆H₂₉N	236.2(235.2)
6d	C₁₄H₂₇N	210.2(209.2)	6k	C₁₆H₂₃N	230.2(229.2)
6e	C₁₅H₂₉N	224.2(223.2)	6l	C₁₇H₂₅N	244.2(243.2)

Table 2 Appearance, yields, HRMS and IR data of target compounds 7 and 8a

Compd.	Appearance	Yield(%)	Chemical formula	ESI-HRMS^b(calcd.), m/z		IR(KBr), $ν ˙$ /cm^-1
7a	Yellow liquid	85.9	C₁₆H₂₁NO₂	260.1646(260.1645)		3031, 2967, 2918, 2857, 1729, 1408, 1278, 1119, 930, 850
7b	Yellow liquid	85.3	C₁₆H₁₉Cl₂NO₂	328.0867(328.0866)		3088, 2967, 2926, 2856, 1732, 1582, 1548, 1442, 1358, 1277, 1155, 933, 816
7c	Yellow liquid	70.3	C₁₇H₂₂ClNO₃	324.1364(324.1361)		3091, 2951, 2925, 2856, 1732, 1604, 1555, 1463, 1384, 1357, 1317, 1265, 1153, 1042, 938, 887
7d	Yellow liquid	74.5	C₁₆H₂₀ClNO₂	294.1259(294.1255)		3064, 2968, 2918, 2857, 1731, 1591, 1552, 1462, 1368, 1291, 1259, 1145, 1107, 931, 860
7e	Yellow liquid	63.2	C₁₇H₂₃NO₃	290.1750(290.1751)		2968, 2925, 2857, 1731, 1674, 1611, 1564, 1553, 1449, 1386, 1292, 1259, 1215, 1039, 935, 840
8a	Yellow liquid	63.8	C₁₆H₂₂N₂O	259.1806(259.1805)		3304, 3045, 2965, 2924, 2855, 1645, 1600, 1542, 1490, 1449, 1297, 1066, 846
8b	White solid	85.5	C₁₆H₂₀Cl₂N₂O	327.1026(327.1025)		3273, 3129, 3083, 2964, 2924, 2854, 1644, 1447, 1358, 1294, 1158, 820
8c	White solid	69.5	C₁₇H₂₃ClN₂O₂	323.1519(323.1521)		3273, 2924, 2856, 1645, 1603, 1538, 1463, 1379, 1162, 1047, 873
8d	Yellow liquid	68.5	C₁₇H₂₂Cl₂N₂O	363.1000(363.1001)		3270, 3068, 2971, 2930, 2856, 1644, 1583, 1533, 1455, 1381, 1309, 1286, 1264, 1164, 873, 822
8e	Yellow liquid	83.2	C₁₈H₂₄Cl₂N₂O	355.1339(355.1338)		3270, 3068, 2971, 2930, 2856, 1644, 1583, 1533, 1455, 1361, 1164, 873, 822
8f	Yellow liquid	91.9	C₁₉H₂₆Cl₂N₂O	369.1496(369.1495)	3269, 3068, 2966, 2930, 2876, 1643, 1583, 1534, 1437, 1406, 1361, 1261, 1164, 872, 822
8g	Yellow liquid	68.6	C₂₀H₂₈Cl₂N₂O	405.1472(405.1471)	3068, 2963, 2928, 2872, 1643, 1583, 1534, 1436, 1361, 1290, 1266, 1164, 872, 822
8h	Yellow liquid	59.3	C₂₁H₃₀Cl₂N₂O	419.1628(419.1627)	3068, 2960, 2930, 2859, 1642, 1583, 1534, 1438, 1360, 1263, 1163, 872, 822
8i	Yellow liquid	91.8	C₂₂H₃₂Cl₂N₂O	411.1967(411.1964)	3068, 2958, 2929, 2858, 1642, 1583, 1534, 1438, 1360, 1264, 1163, 872, 822
8j	Yellow liquid	83.7	C₁₉H₂₆Cl₂N₂O	369.1496(369.1495)	3066, 2973, 2929, 1638, 1582, 1534, 1449, 1406, 1360, 1164, 872, 823
8k	Yellow liquid	90.7	C₂₀H₂₈Cl₂N₂O	383.1655(383.1651)	3068, 2962, 2930, 2873, 1642, 1583, 1534, 1438, 1383, 1360, 1164, 872, 822
8l	Yellow liquid	80.0	C₂₀H₂₈Cl₂N₂O	383.1649(383.1651)	3068, 2967, 2925, 1645, 1580, 1534, 1421, 1361, 1261,1164, 871, 823
8m	Yellow liquid	60.1	C₂₂H₃₀Cl₂N₂O	409.1808(409.1808)	3068, 2931, 2856, 1714, 1634, 1582, 1533, 1453, 1405, 1361, 1253, 1164, 1102, 871, 822
8n	Yellow liquid	67.3	C₂₂H₂₄Cl₂N₂O	403.1336(403.1338)	3066, 2967, 2924, 2855, 1654, 1594, 1582, 1536, 1494, 1420, 1384, 1359, 1293, 1164, 874, 819
8o	Yellow liquid	91.8	C₂₃H₂₆Cl₂N₂O	417.1493(417.1495)	3066, 3030, 2967, 2924, 2855, 1643, 1583, 1535, 1496, 1451, 1360, 1263, 1164, 872, 822

Table 2 Appearance, yields, HRMS and IR data of target compounds 7 and 8a

Compd.	Appearance	Yield(%)	Chemical formula	ESI-HRMS^b(calcd.), m/z		IR(KBr), $ν ˙$ /cm^-1
7a	Yellow liquid	85.9	C₁₆H₂₁NO₂	260.1646(260.1645)		3031, 2967, 2918, 2857, 1729, 1408, 1278, 1119, 930, 850
7b	Yellow liquid	85.3	C₁₆H₁₉Cl₂NO₂	328.0867(328.0866)		3088, 2967, 2926, 2856, 1732, 1582, 1548, 1442, 1358, 1277, 1155, 933, 816
7c	Yellow liquid	70.3	C₁₇H₂₂ClNO₃	324.1364(324.1361)		3091, 2951, 2925, 2856, 1732, 1604, 1555, 1463, 1384, 1357, 1317, 1265, 1153, 1042, 938, 887
7d	Yellow liquid	74.5	C₁₆H₂₀ClNO₂	294.1259(294.1255)		3064, 2968, 2918, 2857, 1731, 1591, 1552, 1462, 1368, 1291, 1259, 1145, 1107, 931, 860
7e	Yellow liquid	63.2	C₁₇H₂₃NO₃	290.1750(290.1751)		2968, 2925, 2857, 1731, 1674, 1611, 1564, 1553, 1449, 1386, 1292, 1259, 1215, 1039, 935, 840
8a	Yellow liquid	63.8	C₁₆H₂₂N₂O	259.1806(259.1805)		3304, 3045, 2965, 2924, 2855, 1645, 1600, 1542, 1490, 1449, 1297, 1066, 846
8b	White solid	85.5	C₁₆H₂₀Cl₂N₂O	327.1026(327.1025)		3273, 3129, 3083, 2964, 2924, 2854, 1644, 1447, 1358, 1294, 1158, 820
8c	White solid	69.5	C₁₇H₂₃ClN₂O₂	323.1519(323.1521)		3273, 2924, 2856, 1645, 1603, 1538, 1463, 1379, 1162, 1047, 873
8d	Yellow liquid	68.5	C₁₇H₂₂Cl₂N₂O	363.1000(363.1001)		3270, 3068, 2971, 2930, 2856, 1644, 1583, 1533, 1455, 1381, 1309, 1286, 1264, 1164, 873, 822
8e	Yellow liquid	83.2	C₁₈H₂₄Cl₂N₂O	355.1339(355.1338)		3270, 3068, 2971, 2930, 2856, 1644, 1583, 1533, 1455, 1361, 1164, 873, 822
8f	Yellow liquid	91.9	C₁₉H₂₆Cl₂N₂O	369.1496(369.1495)	3269, 3068, 2966, 2930, 2876, 1643, 1583, 1534, 1437, 1406, 1361, 1261, 1164, 872, 822
8g	Yellow liquid	68.6	C₂₀H₂₈Cl₂N₂O	405.1472(405.1471)	3068, 2963, 2928, 2872, 1643, 1583, 1534, 1436, 1361, 1290, 1266, 1164, 872, 822
8h	Yellow liquid	59.3	C₂₁H₃₀Cl₂N₂O	419.1628(419.1627)	3068, 2960, 2930, 2859, 1642, 1583, 1534, 1438, 1360, 1263, 1163, 872, 822
8i	Yellow liquid	91.8	C₂₂H₃₂Cl₂N₂O	411.1967(411.1964)	3068, 2958, 2929, 2858, 1642, 1583, 1534, 1438, 1360, 1264, 1163, 872, 822
8j	Yellow liquid	83.7	C₁₉H₂₆Cl₂N₂O	369.1496(369.1495)	3066, 2973, 2929, 1638, 1582, 1534, 1449, 1406, 1360, 1164, 872, 823
8k	Yellow liquid	90.7	C₂₀H₂₈Cl₂N₂O	383.1655(383.1651)	3068, 2962, 2930, 2873, 1642, 1583, 1534, 1438, 1383, 1360, 1164, 872, 822
8l	Yellow liquid	80.0	C₂₀H₂₈Cl₂N₂O	383.1649(383.1651)	3068, 2967, 2925, 1645, 1580, 1534, 1421, 1361, 1261,1164, 871, 823
8m	Yellow liquid	60.1	C₂₂H₃₀Cl₂N₂O	409.1808(409.1808)	3068, 2931, 2856, 1714, 1634, 1582, 1533, 1453, 1405, 1361, 1253, 1164, 1102, 871, 822
8n	Yellow liquid	67.3	C₂₂H₂₄Cl₂N₂O	403.1336(403.1338)	3066, 2967, 2924, 2855, 1654, 1594, 1582, 1536, 1494, 1420, 1384, 1359, 1293, 1164, 874, 819
8o	Yellow liquid	91.8	C₂₃H₂₆Cl₂N₂O	417.1493(417.1495)	3066, 3030, 2967, 2924, 2855, 1643, 1583, 1535, 1496, 1451, 1360, 1263, 1164, 872, 822

Table 3 1H NMR and 13C NMR data of target compounds 7 and 8*

Compd.	¹H NMR(300 MHz, CDCl₃), δ	¹³C NMR(75 MHz, CDCl₃), δ
7a	8.71—8.73(m, 2H, ArH), 7.80—7.82(m, 2H, ArH), 5.37—5.42(m, 1H, C═CH), 5.03—5.05(m, 1H, C═CH), 4.83(d, J=7.1 Hz, 2H, CH₂), 2.00—2.12(m, 4H, CH₂CH₂), 1.74(s, 3H, CH₃), 1.63(s, 3H, CH₃), 1.56(s, 3H, CH₃)	164.62, 150.06, 142.86, 137.35, 131.42, 123.24, 122.48, 117.36, 62.18, 39.15, 25.84, 25.22, 17.25, 16.13
7b	7.80—7.81(m, 2H, ArH), 5.41—5.46(m, 1H, C═CH), 5.06—5.09(m, 1H, C═CH), 4.88(d, J=7.3 Hz, 2H, CH₂), 2.07—2.16(m, 4H, CH₂CH₂), 1.68—1.77 [m, 6H, C(CH₃)₂], 1.61(s, 3H, CH₃)	162.24, 151.00, 143.75, 142.53, 131.51, 123.17, 122.24, 116.80, 62.94, 39.13, 25.83, 25.25, 17.29, 16.19
7c	7.44(d, J=1.1 Hz, 1H, ArH), 7.23(d, J=1.1 Hz, 1H, ArH), 5.43—5.48(m, 1H, C═CH), 5.07—5.12(m, 1H, C═CH), 4.86(d, J=7.2 Hz, 2H, CH₂), 3.97(s, 3H, OCH₃), 2.05—2.17(m, 4H, CH₂CH₂), 1.78(s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.62(s, 3H, CH₃)	163.99, 163.47, 148.80, 143.14, 142.46, 131.53, 123.24, 117.19, 115.35, 109.30, 62.42, 54.07, 39.15, 25.87, 25.27, 17.30, 16.18
7d	8.53(dd, J₁=5.1 Hz, J₂=0.7 Hz, 1H, ArH), 7.89(dd, J₁=1.3 Hz, J₂=0.8 Hz, 1H, ArH), 7.78(dd, J₁=5.1 Hz, J₂=1.4 Hz, 1H, ArH), 5.42—5.48(m, 1H, C═CH), 5.06—5.11(m, 1H, C═CH), 4.88(d, J=7.2 Hz, 2H, CH₂), 2.07—2.16(m, 4H, CH₂CH₂), 1.78(s, 3H, CH₃), 1.68(s, 3H, CH₃), 1.61(s, 3H, CH₃)	163.23, 151.93, 149.98, 143.18, 140.23, 131.35, 123.54, 123.18, 121.19, 117.08, 62.47, 39.08, 25.79, 25.19, 17.22, 16.10
7e	8.29(dd, J₁=5.3 Hz, J₂=0.6 Hz, 1H, ArH), 7.43(dd, J₁=5.3 Hz, J₂=1.4 Hz, 1H, ArH), 7.34(d, J=0.4 Hz, 1H, ArH), 5.44—5.49(m, 1H, C═CH), 5.08—5.13(m, 1H, C═CH), 4.87(d, J=7.1 Hz, 2H, CH₂), 3.98(s, 3H, OCH₃), 2.06—2.17(m, 4H, CH₂CH₂), 1.79(s, 3H, CH₃), 1.70(s, 3H, CH₃), 1.62(s, 3H, CH₃)	164.68, 164.47, 147.24, 142.79, 140.20, 131.53, 123.29, 117.45, 115.41, 110.87, 62.12, 53.42, 39.17, 25.91, 25.29, 17.32, 16.20
8a	8.71—8.73(m, 2H, ArH), 7.60—7.62(m, 2H, ArH), 6.28(brs, 1H, NH), 5.26—5.31(m, 1H, C═CH), 5.06—5.10(m, 1H, C═CH), 4.04—4.13(m, 2H, CH₂), 2.01—2.11(m, 4H, CH₂CH₂), 1.68—1.72 [m, 6H, C(CH₃)₂], 1.60(s, 3H, CH₃)		165.09, 149.63, 141.58, 139.27, 131.16, 123.31, 120.87, 119.19, 39.03, 37.76, 25.92, 25.18, 17.19, 15.82
8b	7.57(s, 2H, ArH), 6.08(brs, 1H, NH), 5.24—5.29(m, 1H, C═CH), 5.06—5.08(m, 1H, C═CH), 4.05(t, J=5.9 Hz, 2H, CH₂), 2.03—2.12(m, 4H, CH₂CH₂), 1.72—1.69 [m, 6H, C(CH₃)₂], 1.61(s, 3H, CH₃)		162.61, 150.98, 146.81, 140.86, 131.52, 123.26, 120.44, 118.23, 39.11, 38.08, 25.97, 25.29, 17.32, 16.03
8c	7.21(d, J=1.1 Hz, 1H, ArH), 6.97(d, J=1.1 Hz, 1H, ArH), 6.42(s, 1H, NH), 5.25—5.39(m, 1H, C═CH), 5.07—5.11(m, 1H, C═CH), 4.03(t, J=6.1 Hz, 2H, CH₂), 3.96(s, 3H, OCH₃) 2.02—2.12(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.70(s, 3H, CH₃), 1.62(s, 3H, CH₃)		164.00, 163.89, 148.94, 146.78, 140.61, 131.50, 123.36, 118.63, 113.63, 106.88, 54.09, 39.13, 37.84, 26.00, 25.31, 17.33, 16.01
8d	7.26 and 7.27(2s, 2H, ArH), 5.07—5.21(m, 2H, C═CH), 4.14 and 3.76(2d, J=7.1, 6.7 Hz, 2H, CH₂), 3.04 and 2.85(2s, 3H, N—CH₃), 2.03—2.10(m, 4H, CH₂CH₂), 1.74 and 1.52(2s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.61(s, 3H, CH₃)		165.66, 165.20, 150.49, 150.43, 149.07, 141.13, 140.59, 131.48, 131.20, 123.37, 123.11, 120.17, 120.12, 117.69, 117.51, 48.65, 44.19, 39.15, 39.00, 35.64, 32.15, 25.86, 25.80, 25.25, 17.27, 15.82, 15.71
8e	7.25 and 7.27(2s, 2H, ArH), 5.05—5.22(m, 2H, C═CH), 4.14 and 3.75(2d, J=7.0, 5.8 Hz, 2H, CH₂), 3.48—3.55 and 3.14—3.21(2m, 2H, N—CH₂), 2.05—2.09(m, 4H, CH₂CH₂), 1.69(s, 3H, CH₃), 1.62 [d, J=4.7 Hz, 6H, C(CH₃)₂], 1.22 and 1.11(2t, J=7.2, 7.1 Hz, 3H, CH₃)		165.37, 150.55, 150.42, 149.45, 149.33, 140.17, 131.52, 131.21, 123.40, 123.15, 120.04, 119.72, 118.41, 118.28, 46.25, 42.28, 41.29, 39.70, 39.13, 39.00, 25.80, 25.26, 17.29, 15.83, 15.71, 13.55, 12.08
8f	7.22(d, J=2.0 Hz, 2H, ArH), 5.07—5.30(m, 2H, C═CH), 4.13 and 3.74(2d, J=6.9, 6.7 Hz, 2H, CH₂), 3.42 and 3.07(2t, J=7.6, 7.5 Hz, 2H, N—CH₂), 2.04—2.11(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.48(s, 2H, CH₂), 0.97 and 0.80(2t, J=7.4 Hz, 3H, CH₃)		165.64, 150.51, 150.40, 149.45, 140.20, 140.12, 131.48, 131.18, 123.40, 123.14, 119.98, 119.91, 118.39, 118.23, 49.23, 46.58, 46.31, 41.62, 39.11, 38.97, 25.79, 25.25, 21.26, 20.10, 17.27, 15.82, 15.67, 10.97, 10.65
8g	7.23(s, 2H, ArH), 5.06—5.23(m, 2H, C═CH), 4.13 and 3.74(2d, J=6.8, 6.4 Hz, 2H, CH₂), 3.45 and 3.09(2t, J=7.6 Hz, 2H, N—CH₂), 2.04—2.11(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.48(s, 2H, CH₂), 0.97 and 0.80(2t, J=7.4 Hz, 3H, CH₃)		166.14, 165.95, 150.54, 150.46, 149.64, 140.27, 140.18, 131.55, 131.25, 123.39, 123.13, 120.24, 119.88, 118.25, 188.03, 55.00, 51.34, 46.89, 41.74, 39.13, 38.98, 26.39, 26.23, 25.88, 25.79, 25.29, 19.79, 19.43, 17.32, 15.90, 15.69
8h	7.22(d, J=2.0 Hz, 2H, ArH), 5.06—5.23(m, 2H, C═CH), 4.13 and 3.74(2d, J=6.8, 6.6 Hz, 2H, CH₂), 3.44 and 3.08(2t, J=7.7, 7.6 Hz, 2H, N—CH₂), 2.04—2.11(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.12—1.58(m, 6H, CH₂CH₂CH₂), 0.83—0.95(m, 3H, CH₃)		165.53, 150.51, 150.40, 149.47, 140.12, 131.48, 131.18, 123.39, 123.14, 119.98, 119.88, 118.40, 118.25, 47.60, 46.53, 44.71, 41.65, 39.12, 38.98, 28.71, 28.22, 27.64, 26.49, 25.80, 25.24, 21.98, 21.68, 17.27, 15.85, 15.69, 13.54, 13.37
8i	7.23(s, 2H, ArH), 5.05—5.23(m, 2H, C═CH), 4.13 and 3.74(2d, J=7.1, 6.5 Hz, 2H, CH₂), 3.44 and 3.08(2t, J=7.7, 7.1 Hz, 2H, N—CH₂), 2.06—2.11(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.17—1.57(m, 8H, CH₂CH₂CH₂CH₂), 0.84—0.91(m, 3H, CH₃)		165.51, 150.50, 150.39, 149.47, 140.17, 140.09, 131.46, 131.16, 123.39, 123.14, 119.98, 119.89, 118.41, 118.26, 47.60, 46.53, 44.73, 41.64, 39.12, 38.97, 31.08, 30.75, 27.92, 26.77, 26.23, 25.80, 25.74, 25.24, 22.12, 21.97, 17.26, 15.84, 15.68, 13.56, 13.44
8j	7.21(s, 2H, ArH), 5.01—5.24(m, 2H, C═CH), 4.64—4.72 and 4.00—4.02(2m, 2H, CH₂), 3.68—3.79(m, 2H, CH₂), 2.01—2.11(m, 4H, CH₂CH₂), 1.73(s, 3H, CH₃), 1.68(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.34(s, 1H, CH), 1.27 and 1.18[2d, J=6.8, 6.5 Hz, 6H, C(CH₃)₂]			165.97, 165.22, 150.56, 150.24, 149.94, 138.24, 137.04, 131.41, 131.00, 123.57, 123.27, 120.78, 119.92, 119.46, 50.13, 46.37, 42.72, 38.88, 38.38, 25.81, 25.24, 20.88, 19.72, 17.28, 15.79, 15.56
8k	7.19—7.21(m, 2H, ArH), 5.03—5.23(m, 2H, C═CH), 4.14 and 3.75(2d, J=7.0, 6.4 Hz, 2H, CH₂), 3.31 and 2.95(2d, J=7.6, 7.5 Hz, 2H, N—CH₂), 2.04—2.09(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.45(s, 1H, CH), 0.97 and 0.81[2d, J=6.7 Hz, 6H,(CH₃)₂]			165.58, 150.54, 150.43, 149.46, 140.16, 131.53, 131.22, 123.40, 123.14, 119.98, 119.89, 118.38, 118.23, 47.39, 46.54, 44.47, 41.66, 39.14, 38.99, 30.11, 28.94, 25.81, 25.26, 19.82, 19.33, 17.29, 15.88, 15.71, 13.42, 13.15
8l	7.19(s, 2H, ArH), 5.05—5.08(m, 2H, C═CH), 3.77(d, J=5.6 Hz, 2H, CH₂), 2.01—2.11(m, 4H, CH₂CH₂), 1.69(s, 3H, CH₃), 1.62(s, 3H, CH₃), 1.52[s, 9H, C(CH₃)₃], 1.34(s, 3H, CH₃)			167.08, 151.36, 150.28, 137.39, 131.44, 123.35, 121.75, 119.50, 57.71, 45.35, 38.81, 28.06, 28.01, 25.77, 25.30, 17.35, 15.66
8m	7.21(s, 2H, ArH), 5.02—5.15(m, 2H, C═CH), 4.02 and 3.69(2d, J=5.4, 5.9 Hz, 2H, CH₂), 4.34 and 3.23(2t, J=14.1, 12.5 Hz, 2H, N—CH₂), 2.00—2.17(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.68(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.73—1.85 and 1.05—1.57(2m, 10H, CH₂CH₂CH₂CH₂CH₂)			166.07, 165.38, 150.60, 150.22, 149.99, 137.98, 136.96, 131.44, 131.02, 123.58, 123.28, 120.97, 119.93, 119.45, 58.71, 54.37, 53.13, 43.10, 39.49, 38.86, 30.17, 25.86, 25.43, 25.24, 17.30, 15.86, 15.58
8n	7.24—7.30(m, 4H, ArH), 7.01—7.08(m, 2H, ArH), 7.02(d, J=6.9 Hz, 1H, ArH), 5.28—5.33(m, 1H, C═CH), 5.01—5.03(m, 1H, C═CH), 4.48(d, J=7.3 Hz, 2H, CH₂), 1.98—2.07(m, 4H, CH₂CH₂), 1.68(s, 3H, CH₃), 1.57(t, J=2.6 Hz, 3H, CH₃), 1.50(s, 3H, CH₃)			164.52, 149.94, 148.83, 141.01, 140.73, 131.22, 129.25, 127.74, 127.67, 123.46, 121.54, 117.63, 47.63, 39.14, 25.91, 25.32, 17.32, 15.75
8o	7.24—7.41(m, 7H, ArH), 5.06—5.30(m, 2H, C═CH), 4.70 and 4.37(2s, 2H, CH₂), 4.11 and 3.67(2d, J=6.8, 6.5 Hz, 2H, CH₂), 2.04—2.11(m, 4H, CH₂CH₂), 1.70(s, 3H, CH₃), 1.63(s, 3H, CH₃), 1.38(s, 3H, CH₃)			166.07, 150.59, 149.03, 141.27, 140.69, 135.99, 135.30, 131.60, 131.31, 128.66, 128.43, 128.01, 127.67, 127.46, 126.35, 123.52, 123.28, 120.06, 117.98, 117.61, 53.17, 51.03, 47.25, 45.83, 41.93, 39.04, 25.83, 25.37, 17.41, 15.82

Table 3 1H NMR and 13C NMR data of target compounds 7 and 8*

Compd.	¹H NMR(300 MHz, CDCl₃), δ	¹³C NMR(75 MHz, CDCl₃), δ
7a	8.71—8.73(m, 2H, ArH), 7.80—7.82(m, 2H, ArH), 5.37—5.42(m, 1H, C═CH), 5.03—5.05(m, 1H, C═CH), 4.83(d, J=7.1 Hz, 2H, CH₂), 2.00—2.12(m, 4H, CH₂CH₂), 1.74(s, 3H, CH₃), 1.63(s, 3H, CH₃), 1.56(s, 3H, CH₃)	164.62, 150.06, 142.86, 137.35, 131.42, 123.24, 122.48, 117.36, 62.18, 39.15, 25.84, 25.22, 17.25, 16.13
7b	7.80—7.81(m, 2H, ArH), 5.41—5.46(m, 1H, C═CH), 5.06—5.09(m, 1H, C═CH), 4.88(d, J=7.3 Hz, 2H, CH₂), 2.07—2.16(m, 4H, CH₂CH₂), 1.68—1.77 [m, 6H, C(CH₃)₂], 1.61(s, 3H, CH₃)	162.24, 151.00, 143.75, 142.53, 131.51, 123.17, 122.24, 116.80, 62.94, 39.13, 25.83, 25.25, 17.29, 16.19
7c	7.44(d, J=1.1 Hz, 1H, ArH), 7.23(d, J=1.1 Hz, 1H, ArH), 5.43—5.48(m, 1H, C═CH), 5.07—5.12(m, 1H, C═CH), 4.86(d, J=7.2 Hz, 2H, CH₂), 3.97(s, 3H, OCH₃), 2.05—2.17(m, 4H, CH₂CH₂), 1.78(s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.62(s, 3H, CH₃)	163.99, 163.47, 148.80, 143.14, 142.46, 131.53, 123.24, 117.19, 115.35, 109.30, 62.42, 54.07, 39.15, 25.87, 25.27, 17.30, 16.18
7d	8.53(dd, J₁=5.1 Hz, J₂=0.7 Hz, 1H, ArH), 7.89(dd, J₁=1.3 Hz, J₂=0.8 Hz, 1H, ArH), 7.78(dd, J₁=5.1 Hz, J₂=1.4 Hz, 1H, ArH), 5.42—5.48(m, 1H, C═CH), 5.06—5.11(m, 1H, C═CH), 4.88(d, J=7.2 Hz, 2H, CH₂), 2.07—2.16(m, 4H, CH₂CH₂), 1.78(s, 3H, CH₃), 1.68(s, 3H, CH₃), 1.61(s, 3H, CH₃)	163.23, 151.93, 149.98, 143.18, 140.23, 131.35, 123.54, 123.18, 121.19, 117.08, 62.47, 39.08, 25.79, 25.19, 17.22, 16.10
7e	8.29(dd, J₁=5.3 Hz, J₂=0.6 Hz, 1H, ArH), 7.43(dd, J₁=5.3 Hz, J₂=1.4 Hz, 1H, ArH), 7.34(d, J=0.4 Hz, 1H, ArH), 5.44—5.49(m, 1H, C═CH), 5.08—5.13(m, 1H, C═CH), 4.87(d, J=7.1 Hz, 2H, CH₂), 3.98(s, 3H, OCH₃), 2.06—2.17(m, 4H, CH₂CH₂), 1.79(s, 3H, CH₃), 1.70(s, 3H, CH₃), 1.62(s, 3H, CH₃)	164.68, 164.47, 147.24, 142.79, 140.20, 131.53, 123.29, 117.45, 115.41, 110.87, 62.12, 53.42, 39.17, 25.91, 25.29, 17.32, 16.20
8a	8.71—8.73(m, 2H, ArH), 7.60—7.62(m, 2H, ArH), 6.28(brs, 1H, NH), 5.26—5.31(m, 1H, C═CH), 5.06—5.10(m, 1H, C═CH), 4.04—4.13(m, 2H, CH₂), 2.01—2.11(m, 4H, CH₂CH₂), 1.68—1.72 [m, 6H, C(CH₃)₂], 1.60(s, 3H, CH₃)		165.09, 149.63, 141.58, 139.27, 131.16, 123.31, 120.87, 119.19, 39.03, 37.76, 25.92, 25.18, 17.19, 15.82
8b	7.57(s, 2H, ArH), 6.08(brs, 1H, NH), 5.24—5.29(m, 1H, C═CH), 5.06—5.08(m, 1H, C═CH), 4.05(t, J=5.9 Hz, 2H, CH₂), 2.03—2.12(m, 4H, CH₂CH₂), 1.72—1.69 [m, 6H, C(CH₃)₂], 1.61(s, 3H, CH₃)		162.61, 150.98, 146.81, 140.86, 131.52, 123.26, 120.44, 118.23, 39.11, 38.08, 25.97, 25.29, 17.32, 16.03
8c	7.21(d, J=1.1 Hz, 1H, ArH), 6.97(d, J=1.1 Hz, 1H, ArH), 6.42(s, 1H, NH), 5.25—5.39(m, 1H, C═CH), 5.07—5.11(m, 1H, C═CH), 4.03(t, J=6.1 Hz, 2H, CH₂), 3.96(s, 3H, OCH₃) 2.02—2.12(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.70(s, 3H, CH₃), 1.62(s, 3H, CH₃)		164.00, 163.89, 148.94, 146.78, 140.61, 131.50, 123.36, 118.63, 113.63, 106.88, 54.09, 39.13, 37.84, 26.00, 25.31, 17.33, 16.01
8d	7.26 and 7.27(2s, 2H, ArH), 5.07—5.21(m, 2H, C═CH), 4.14 and 3.76(2d, J=7.1, 6.7 Hz, 2H, CH₂), 3.04 and 2.85(2s, 3H, N—CH₃), 2.03—2.10(m, 4H, CH₂CH₂), 1.74 and 1.52(2s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.61(s, 3H, CH₃)		165.66, 165.20, 150.49, 150.43, 149.07, 141.13, 140.59, 131.48, 131.20, 123.37, 123.11, 120.17, 120.12, 117.69, 117.51, 48.65, 44.19, 39.15, 39.00, 35.64, 32.15, 25.86, 25.80, 25.25, 17.27, 15.82, 15.71
8e	7.25 and 7.27(2s, 2H, ArH), 5.05—5.22(m, 2H, C═CH), 4.14 and 3.75(2d, J=7.0, 5.8 Hz, 2H, CH₂), 3.48—3.55 and 3.14—3.21(2m, 2H, N—CH₂), 2.05—2.09(m, 4H, CH₂CH₂), 1.69(s, 3H, CH₃), 1.62 [d, J=4.7 Hz, 6H, C(CH₃)₂], 1.22 and 1.11(2t, J=7.2, 7.1 Hz, 3H, CH₃)		165.37, 150.55, 150.42, 149.45, 149.33, 140.17, 131.52, 131.21, 123.40, 123.15, 120.04, 119.72, 118.41, 118.28, 46.25, 42.28, 41.29, 39.70, 39.13, 39.00, 25.80, 25.26, 17.29, 15.83, 15.71, 13.55, 12.08
8f	7.22(d, J=2.0 Hz, 2H, ArH), 5.07—5.30(m, 2H, C═CH), 4.13 and 3.74(2d, J=6.9, 6.7 Hz, 2H, CH₂), 3.42 and 3.07(2t, J=7.6, 7.5 Hz, 2H, N—CH₂), 2.04—2.11(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.48(s, 2H, CH₂), 0.97 and 0.80(2t, J=7.4 Hz, 3H, CH₃)		165.64, 150.51, 150.40, 149.45, 140.20, 140.12, 131.48, 131.18, 123.40, 123.14, 119.98, 119.91, 118.39, 118.23, 49.23, 46.58, 46.31, 41.62, 39.11, 38.97, 25.79, 25.25, 21.26, 20.10, 17.27, 15.82, 15.67, 10.97, 10.65
8g	7.23(s, 2H, ArH), 5.06—5.23(m, 2H, C═CH), 4.13 and 3.74(2d, J=6.8, 6.4 Hz, 2H, CH₂), 3.45 and 3.09(2t, J=7.6 Hz, 2H, N—CH₂), 2.04—2.11(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.48(s, 2H, CH₂), 0.97 and 0.80(2t, J=7.4 Hz, 3H, CH₃)		166.14, 165.95, 150.54, 150.46, 149.64, 140.27, 140.18, 131.55, 131.25, 123.39, 123.13, 120.24, 119.88, 118.25, 188.03, 55.00, 51.34, 46.89, 41.74, 39.13, 38.98, 26.39, 26.23, 25.88, 25.79, 25.29, 19.79, 19.43, 17.32, 15.90, 15.69
8h	7.22(d, J=2.0 Hz, 2H, ArH), 5.06—5.23(m, 2H, C═CH), 4.13 and 3.74(2d, J=6.8, 6.6 Hz, 2H, CH₂), 3.44 and 3.08(2t, J=7.7, 7.6 Hz, 2H, N—CH₂), 2.04—2.11(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.12—1.58(m, 6H, CH₂CH₂CH₂), 0.83—0.95(m, 3H, CH₃)		165.53, 150.51, 150.40, 149.47, 140.12, 131.48, 131.18, 123.39, 123.14, 119.98, 119.88, 118.40, 118.25, 47.60, 46.53, 44.71, 41.65, 39.12, 38.98, 28.71, 28.22, 27.64, 26.49, 25.80, 25.24, 21.98, 21.68, 17.27, 15.85, 15.69, 13.54, 13.37
8i	7.23(s, 2H, ArH), 5.05—5.23(m, 2H, C═CH), 4.13 and 3.74(2d, J=7.1, 6.5 Hz, 2H, CH₂), 3.44 and 3.08(2t, J=7.7, 7.1 Hz, 2H, N—CH₂), 2.06—2.11(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.17—1.57(m, 8H, CH₂CH₂CH₂CH₂), 0.84—0.91(m, 3H, CH₃)		165.51, 150.50, 150.39, 149.47, 140.17, 140.09, 131.46, 131.16, 123.39, 123.14, 119.98, 119.89, 118.41, 118.26, 47.60, 46.53, 44.73, 41.64, 39.12, 38.97, 31.08, 30.75, 27.92, 26.77, 26.23, 25.80, 25.74, 25.24, 22.12, 21.97, 17.26, 15.84, 15.68, 13.56, 13.44
8j	7.21(s, 2H, ArH), 5.01—5.24(m, 2H, C═CH), 4.64—4.72 and 4.00—4.02(2m, 2H, CH₂), 3.68—3.79(m, 2H, CH₂), 2.01—2.11(m, 4H, CH₂CH₂), 1.73(s, 3H, CH₃), 1.68(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.34(s, 1H, CH), 1.27 and 1.18[2d, J=6.8, 6.5 Hz, 6H, C(CH₃)₂]			165.97, 165.22, 150.56, 150.24, 149.94, 138.24, 137.04, 131.41, 131.00, 123.57, 123.27, 120.78, 119.92, 119.46, 50.13, 46.37, 42.72, 38.88, 38.38, 25.81, 25.24, 20.88, 19.72, 17.28, 15.79, 15.56
8k	7.19—7.21(m, 2H, ArH), 5.03—5.23(m, 2H, C═CH), 4.14 and 3.75(2d, J=7.0, 6.4 Hz, 2H, CH₂), 3.31 and 2.95(2d, J=7.6, 7.5 Hz, 2H, N—CH₂), 2.04—2.09(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.69(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.45(s, 1H, CH), 0.97 and 0.81[2d, J=6.7 Hz, 6H,(CH₃)₂]			165.58, 150.54, 150.43, 149.46, 140.16, 131.53, 131.22, 123.40, 123.14, 119.98, 119.89, 118.38, 118.23, 47.39, 46.54, 44.47, 41.66, 39.14, 38.99, 30.11, 28.94, 25.81, 25.26, 19.82, 19.33, 17.29, 15.88, 15.71, 13.42, 13.15
8l	7.19(s, 2H, ArH), 5.05—5.08(m, 2H, C═CH), 3.77(d, J=5.6 Hz, 2H, CH₂), 2.01—2.11(m, 4H, CH₂CH₂), 1.69(s, 3H, CH₃), 1.62(s, 3H, CH₃), 1.52[s, 9H, C(CH₃)₃], 1.34(s, 3H, CH₃)			167.08, 151.36, 150.28, 137.39, 131.44, 123.35, 121.75, 119.50, 57.71, 45.35, 38.81, 28.06, 28.01, 25.77, 25.30, 17.35, 15.66
8m	7.21(s, 2H, ArH), 5.02—5.15(m, 2H, C═CH), 4.02 and 3.69(2d, J=5.4, 5.9 Hz, 2H, CH₂), 4.34 and 3.23(2t, J=14.1, 12.5 Hz, 2H, N—CH₂), 2.00—2.17(m, 4H, CH₂CH₂), 1.72(s, 3H, CH₃), 1.68(s, 3H, CH₃), 1.61(s, 3H, CH₃), 1.73—1.85 and 1.05—1.57(2m, 10H, CH₂CH₂CH₂CH₂CH₂)			166.07, 165.38, 150.60, 150.22, 149.99, 137.98, 136.96, 131.44, 131.02, 123.58, 123.28, 120.97, 119.93, 119.45, 58.71, 54.37, 53.13, 43.10, 39.49, 38.86, 30.17, 25.86, 25.43, 25.24, 17.30, 15.86, 15.58
8n	7.24—7.30(m, 4H, ArH), 7.01—7.08(m, 2H, ArH), 7.02(d, J=6.9 Hz, 1H, ArH), 5.28—5.33(m, 1H, C═CH), 5.01—5.03(m, 1H, C═CH), 4.48(d, J=7.3 Hz, 2H, CH₂), 1.98—2.07(m, 4H, CH₂CH₂), 1.68(s, 3H, CH₃), 1.57(t, J=2.6 Hz, 3H, CH₃), 1.50(s, 3H, CH₃)			164.52, 149.94, 148.83, 141.01, 140.73, 131.22, 129.25, 127.74, 127.67, 123.46, 121.54, 117.63, 47.63, 39.14, 25.91, 25.32, 17.32, 15.75
8o	7.24—7.41(m, 7H, ArH), 5.06—5.30(m, 2H, C═CH), 4.70 and 4.37(2s, 2H, CH₂), 4.11 and 3.67(2d, J=6.8, 6.5 Hz, 2H, CH₂), 2.04—2.11(m, 4H, CH₂CH₂), 1.70(s, 3H, CH₃), 1.63(s, 3H, CH₃), 1.38(s, 3H, CH₃)			166.07, 150.59, 149.03, 141.27, 140.69, 135.99, 135.30, 131.60, 131.31, 128.66, 128.43, 128.01, 127.67, 127.46, 126.35, 123.52, 123.28, 120.06, 117.98, 117.61, 53.17, 51.03, 47.25, 45.83, 41.93, 39.04, 25.83, 25.37, 17.41, 15.82

Table 4 Repellent activity of the target compounds against Myzus persicae(5 μg)

Compd.	Repellent activity(%)	Compd.	Repellent activity(%)	Compd.	Repellent activity(%)
7a	41.9±1.6	8d	33.1±4.5	8l	36.2±2.6
7b	59.0±1.6	8e	47.4±2.4	8m	50.7±3.5
7c	51.9±3.2	8f	62.0±1.9	8n	61.0±2.7
7d	62.6±2.6	8g	56.2±3.6	8o	56.1±0.9
7e	21.0±1.8	8h	40.4±2.2	EBF	90.6±1.0
8a	31.7±2.7	8i	43.6±3.1	2b	0.0±0.0
8b	27.7±0.7	8j	47.8±2.3	2d	0.0±0.0
8c	25.5±2.8	8k	44.7±3.2	3	3.5±3.1

Table 5 Insecticidal activity of the target compounds against Myzus persicae(300 μg/mL)

Compd.	Insecticidal activity(%)	Compd.	Insecticidal activity(%)	Compd.	Insecticidal activity(%)
7a	23.5±3.7	8d	70.2±0.3	8l	42.9±4.1
7b	63.2±1.1	8e	57.0±4.2	8m	23.8±3.3
7c	19.9±1.2	8f	51.1±1.5	8n	46.9±5.3
7d	21.3±2.3	8g	30.8±4.6	8o	36.3±4.0
7e	30.5±5.6	8h	19.9±2.5	EBF	40.0±1.1
8a	73.6±3.3	8i	36.8±4.8	Pymetrozine	80.7±3.8
8b	81.1±5.2	8j	20.1±5.7
8c	60.3±1.3	8k	30.2±5.1

Fig.2 1H NMR(A) and 13C NMR spectra(B) of compound 8d at 25(a) and 100 ℃(b)

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