Syntheses and Insecticidal Activities of Nitro Arylideneamino Guanidine Derivatives†

doi:10.7503/cjcu20131258

Abstract

Abstract:

In order to search for better lead compounds with excellent biological activities, a novel series of acyclic neonicotinoids of nitro arylideneamino guanidine derivatives was designed and synthesized from nitroaminoguanidine by the method of linking the active substructures of neonicotiniod insecticides and semicarbazone insecticides. All the target compounds were confirmed by ¹H NMR, IR and elemental analysis. The preliminary bioassay showed that the lethal rates of target compounds to Myzuspersicae were excellent at the concentration of 600 μg/mL. The lethal rates of several compounds, such as 4-2, 4-8, 4-10, 4-16, 4-27, 4-31 and 4-34, were more than 90%. Further research of compounds 4-2, 4-8 and 4-34 against Myzuspersicae, Aphis gossypii and Hyalopterusamygdali blanchard indicated these compounds possessed high activity at low concentrations, especially, the activity of compound 4-8 was better than that of imidacloprid against Hyalopteraamygdali blanchard, its lethal rate was 95.7% compared to imidacloprid(79.4%) at the concentration of 3.13 μg/mL, which confirmed that this compound is worth of research.

Key words: Arylideneamino guanidine derivative, Aphid, Insecticidal activity

CLC Number:

O625.43

TrendMD:

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^†[J]. Chem. J. Chinese Universities, 2014, 35(8): 1703.

Figures/Tables 5

Scheme 1 Synthetic routes of the target compounds

Table 1 Physico-chemical data of compounds 4a

Compd.	R'	R″	m. p./℃	Yield(%)	Elemental analysis(%, calcd.)
Compd.	R'	R″	m. p./℃	Yield(%)	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 CH	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 CH	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 CH	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 CH	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 CH	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 CH	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)
4-31^b	2-Cl-Py-5-yl	H	201—202	76	50.30(50.53)	3.92(3.91)	24.78(25.24)
4-32^b	2-Cl-Py-5-yl	2-Cl	217—218	65	45.88(45.79)	3.47(3.27)	22.60(22.88)
4-33^b	2-Cl-Py-5-yl	4-MeO	197—198	68	49.31(49.66)	4.17(4.13)	22.66(23.16)
4-34^b	2-Cl-Py-5-yl	2-NO₂	228—229	73	44.63(44.51)	3.37(3.18)	25.46(25.94)
4-35^b	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.)
Compd.	R'	R″	m. p./℃	Yield(%)	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 CH	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 CH	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 CH	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 CH	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 CH	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 CH	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)
4-31^b	2-Cl-Py-5-yl	H	201—202	76	50.30(50.53)	3.92(3.91)	24.78(25.24)
4-32^b	2-Cl-Py-5-yl	2-Cl	217—218	65	45.88(45.79)	3.47(3.27)	22.60(22.88)
4-33^b	2-Cl-Py-5-yl	4-MeO	197—198	68	49.31(49.66)	4.17(4.13)	22.66(23.16)
4-34^b	2-Cl-Py-5-yl	2-NO₂	228—229	73	44.63(44.51)	3.37(3.18)	25.46(25.94)
4-35^b	2-Cl-Py-5-yl	4-F	202—203	86	47.38(47.94)	3.37(3.42)	23.31(23.95)

Table 2 1H NMR and IR data of compounds 4

Compd.	¹H NMR(300 MHz, DMSO-d₆), δ	IR(KBr), $ν ˙$ /cm^-1
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), $ν ˙$ /cm^-1
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 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

Table 4 Insecticidal activities of compounds 4-2, 4-8 and 4-34

Insecticidal activity	Concentration/(μg·mL^-1)	Death rate(%)
Insecticidal activity	Concentration/(μg·mL^-1)	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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