Isoxazoline hybridized neolignan compound as well as preparation method and application thereof

Abstract

The invention discloses an isoxazoline hybridized neolignan compound as well as a preparation method and application of the isoxazoline hybridized neolignan compound. The neolignan compound disclosed by the invention is one of isoxazoline magnolol, isoxazoline honokiol, isoxazoline nitrated magnolol and isoxazoline nitrated honokiol derivatives, and has the following chemical general formula: # imgabs0. The neolignan compound disclosed by the invention takes one of magnolol, honokiol, nitrated magnolol or nitrated mangnolia officinalis as a raw material; the preparation method comprises the following steps: by taking triethylamine as alkali and dichloromethane as a solvent, carrying out 1, 3-dipolar cycloaddition reaction on a raw material and alpha-chlorooxime, and separating and purifying to obtain the isoxazoline hybridized neolignan compound. The compound disclosed by the invention has relatively good insecticidal activity on plutella xylostella Linnaeus and Mythimna separata Walker, can be used for preparing a novel efficient insecticide, and is applied to prevention and treatment on the plutella xylostella Linnaeus and the Mythimna separata Walker.

Description

Technical Field

[0001] The invention relates to the technical field of agricultural pesticides, and in particular to an isoxazoline-hybridized new lignan compound and a preparation method and application thereof. Background Art

[0002] Magnolol / honokiol is a new lignan compound derived from the deciduous trees Magnolia officinalis Rehd. et Wils. or Magnolia officinalis var. biloba Rehd. et Wils. of the Magnoliaceae family. It has attracted much attention due to its multiple biological functions such as insecticide, antibacterial, antiviral and anti-tumor. Among them, the literature [Ye YH, Li C, Yang J, et al. Construction of animmobilized acetylcholinesterase column and its application in screening insecticidal constituents from Magnolia officinalis. Pest Management Science, 2016, 71(4): 607-615] and [Guo Meiyan, Chen Yuguo, Wang Xuefen, et al. Application effect of biological pesticides in the control of tobacco budworm / cotton bollworm in tobacco fields. Tobacco Science and Technology, 2020, 53(7): 19-25] reported the insecticidal activity of magnolol / honokiol against various agricultural pests such as brown planthopper, cotton bollworm, armyworm, tobacco aphid and cabbage looper. The literature [Shirui R, Yingming Y, Mengying X, et al. A Chinese herb preparation, honokiol, inhibits Streptococcus mutans biofilm formation. Archives of Oral Biology, 2023, (147): 105610-105610], [Liu T, Pan YL, Lai RF, et al. New mechanism of magnolol and honokiol from Magnolia officinalis against Staphylococcus aureus. Natural Product Communications, 2014, 9 (9): 1307-1309] and [Sun LM, Kai L, et al. The effect of honokiol onergostero biosynthesis and vacuole function in Candida albicans. Microbiol. Biotechnol, 2020, 30 (12): 1835-1842] reported that magnolol / honokiol have good antibacterial activity.The literature [FranckA, Baskaran G, Benjamin L, et al. Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokioland magnolol. Bioorganic & Medicinal Chemistry Letters, 2007, 17 (16): 4428-4431] reported that magnolol / honokiol and magnolol have good anti-HIV type I activity. The literature [Zhang Mingfa, Shen Yaqin, et al. Research progress on the pharmacological effects and mechanisms of honokiol and magnolol against lung cancer. Drug Evaluation Research, 2022, 45 (6): 1213-1220] reported that magnolol / honokiol have a significant inhibitory effect on the proliferation of various cancer cells such as liver cancer cells (HepG2) and lung cancer cells (A549).

[0003] Although previous literature research found that magnolol / honokiol has certain agricultural activities such as insecticide and antibacterial, its biological activity is still relatively mild and there is still a big gap from actual development and application. Summary of the invention

[0004] The purpose of the present invention is to solve the problem that magnolol / honokiol in the prior art have weak insecticidal activity and cannot be applied to actual production, and to provide an isoxazoline hybridized new lignan compound and a preparation method and application thereof.

[0005] In order to solve the above technical problems, the technical solution adopted by the present invention is as follows: an isoxazoline hybridized neolignan compound, wherein the neolignan compound is one of isoxazoline magnolol, isoxazoline and magnolol, isoxazoline nitrated magnolol, and isoxazoline nitrated and magnolol derivatives, and the chemical formula of the isoxazoline hybridized neolignan compound is shown in formula (I):

[0006]

[0007] In the formula (I), R1=OH or OMe; R2 and R3=H or OH or OMe; R4=H or NO2; Ar is any one of the following:

[0008]

[0009] The present invention also provides a method for preparing the above-mentioned isoxazoline hybridized neolignans compound, wherein triethylamine is used as a base and dichloromethane is used as a solvent, and a raw material and α-chlorooxime are subjected to a 1,3-dipolar cycloaddition reaction to obtain the isoxazoline hybridized neolignans compound; the raw material is one of magnolol, honokiol, nitrated magnolol, and nitrated honokiol.

[0010] Preferably, 1 mmol of the raw material is dissolved in 5 mL of dichloromethane, 5 mmol of triethylamine is added at 40° C., and then 4 mmol of α-chlorooxime is added, and the reaction progress is tracked and detected. After the reaction is completed, it is concentrated under reduced pressure and separated by preparative silica gel thin layer chromatography to obtain an isoxazoline hybridized neolignan compound.

[0011] Preferably, the α-chlorooxime is one of α-chlorobenzaldehyde oxime, α-chloro-4-methylbenzaldehyde oxime, α-chloro-3,4-dimethylbenzaldehyde oxime, α-chloro-4-isopropylbenzaldehyde oxime, α-chloro-4-tert-butylbenzaldehyde oxime, α-chloro-2-naphthaldehyde oxime, α-chloro-3-cyanobenzaldehyde oxime, α-chloro-3,4-dichlorobenzaldehyde oxime, α-chloro-3-fluorobenzaldehyde oxime, α-chloro-4-chlorobenzaldehyde oxime or α-chloro-4-bromobenzaldehyde oxime.

[0012] The present invention also provides the use of the isoxazoline hybridized neolignan compound in the preparation of insecticides, and the insecticides are used for Plutella xylostella and Oriental armyworm.

[0013] The beneficial effects of the present invention are as follows: the present invention uses magnolol, honokiol, nitrated magnolol or nitrated honokiol as raw materials to prepare a kind of isoxazoline hybridized neolignan compound (isoxazoline magnolol, isoxazoline honokiol, isoxazoline nitrated magnolol, isoxazoline nitrated honokiol derivatives). The isoxazoline hybridized neolignan compound in the present invention has good insecticidal activity against Plutella xylostella Linnaeus and Mythimnaseparata Walker. Among them, the insecticidal activity of some compounds (derivatives III-3, IV-4, IV-6 and VII-4) against Plutella xylostella is even higher than that of the existing commercial plant-derived insecticide rotenone, and is equivalent to the insecticidal activity of the chemical insecticide tolfenpyrad, showing a strong insecticidal effect; derivative I-9 shows a very strong stomach poison effect against the oriental armyworm. Therefore, the isoxazoline hybridized new lignan compounds (isoxazoline magnolol, isoxazoline and magnolol, isoxazoline nitrated magnolol, isoxazoline nitrated and magnolol derivatives) in the present invention can be used to prepare highly effective new insecticides. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] Figure 1is the hydrogen nuclear magnetic resonance spectrum of compound IV-1;

[0015] Figure 2 This is the carbon NMR spectrum of compound IV-1. DETAILED DESCRIPTION

[0016] The present invention will be further described below in conjunction with the accompanying drawings and specific embodiments.

[0017] Example 1-76

[0018] Example 1-76 Prepare isoxazoline-hybridized new lignan compounds Ⅰ-1-11, Ⅱ-1-11, Ⅲ-1-11, Ⅳ-1-11, Ⅴ-1-8, Ⅵ-1-8, Ⅶ-1-8 and Ⅷ-1-8 in sequence.

[0019] The preparation method is as follows: 1 mmol of the raw material is dissolved in 5 mL of dichloromethane, 5 mmol of triethylamine is added at 40°C, and then 4 mmol of the corresponding α-chlorooxime is added, the reaction progress is tracked and detected, and after the reaction is completed, the reaction is concentrated under reduced pressure, and the desired target product is obtained by separation by silica gel thin layer chromatography. The raw material in Example 1-76 is one of magnolol, honokiol, nitrated magnolol or nitrated honokiol. The raw material table is shown in Table 1.

[0020] The general reaction formula is as follows:

[0021]

[0022] As shown in Table 1, R in compounds Ⅰ-1–11, Ⅱ-1–11, Ⅲ-1–11, Ⅳ-1–11, Ⅴ-1–8, Ⅵ-1–8, Ⅶ-1–8 and Ⅷ-1–8 1 , R 2 , R 3 , R 4 and Ar correspond to the serial numbers in the above reaction formula.

[0023] Table 1 Isoxazoline hybridized neolignan compounds prepared in Examples 1-76

[0024]

[0025]

[0026]

[0027] The physicochemical properties of compound Ⅰ-1 are as follows:

[0028] 1) White solid, melting point 73.5–74.2°C;

[0029] 2) NMR spectrum characteristics of the compound:

[0030] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.63–7.67(m,4H,Ar-H),7.37–7.42(m,8H,Ar-H),7.20(s,1H,Ar-H),7.18(d, J=2.4Hz,1H,Ar-H),6.93(d,J=2.0Hz,1H,Ar-H),6.91(d,J=2.4Hz,1H,Ar-H),5.06–5.14(m,1H,-CH2-C H -CH2-),4.95–5.03(m,1H,-CH2-C H -CH2-),3.86(s,3H,-OCH3),3.79(s,3H,-OCH3),3.26–3.38(m,2H),3.14–3.24(m,2H),3.04–3.12(m,2H),2.85–2.95(m,2H). 13 C NMR (100MHz, CDCl3): δ=156.8,156.5,156.4,155.3,132.5,131.6,131.5,130.6,130.2,130.0,129.9,1 29.7,129.2,129.1,129.0,128.7,128.6,124.8,111.4,110.1,82.0,80.7,55.7,55.4,40.2,39.4,35.9.

[0031] 3) High-resolution mass spectrometric characteristics of the compound:

[0032] Using electrospray ionization: calcd for C 34 H 33 N2O4 + ,([M+H] + )533.2440, found 533.2446.

[0033] The physicochemical properties of compound Ⅰ-2 are as follows:

[0034] 1) White solid, melting point 82.0–82.7°C;

[0035] 2) NMR spectrum characteristics of the compound:

[0036] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ = 7.56 (s, 1H, Ar-H), 7.54 (s, 2H, Ar-H), 7.52 (s, 1H, Ar-H), 7.39–7.42 (m, 1H, Ar-H), 7.38 (d, J = 2.0Hz, 1H, Ar-H),7.19(s,3H,Ar-H),7.18(s,3H,Ar-H),6.92(d,J=1.2Hz,1H,Ar-H),6.90(d,J=2.0Hz,1H,Ar-H),5.04–5.12(m,1H,-CH2-C H -CH2-),4.93–5.00(m,1H,-CH2-C H -CH2-),3.86(s,3H,-OCH3),3.79(s,3H,-OCH3),3.26–3.35(m,2H),3.14 –3.23(m,2H),3.02–3.12(m,2H),2.84–2.94(m,2H),2.36(s,6H,2×-CH3). 13 C NMR (100MHz, CDCl3): δ=156.8,156.5,156.4,155.3,140.2,140.1,132.4,121.6,131.5,130.6,130.2,129.4,129.3,129 .2,129.1,128.9,127.1,126.9,126.6,124.9,111.4,110.0,81.9,80.5,55.7,55.4,40.2,39.6,39.5,35.9,26.9,21.4.

[0037] 3) High-resolution mass spectrometric characteristics of the compound:

[0038] Using electrospray ionization: calcd for C 36 H 37 N2O4 + ,([M+H] + )561.2753, found 561.2756.

[0039] The physicochemical properties of compound Ⅰ-3 are as follows:

[0040] 1) White solid, melting point 81.3–82.0°C;

[0041] 2) NMR spectrum characteristics of the compound:

[0042] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ=7.47(s,1H,Ar-H),7.44(s,1H,Ar-H),7.33–7.41(m,4H,Ar-H),7.19(d,J=7.2Hz,2H,Ar-H),7.14(s,1H Ar-H),7.12(s,1H Ar-H),6.92(s,1H Ar-H),6.90(s,1H Ar-H),5.03–5.11(m,1H,-CH2-C H -CH2-),4.92–5.00(m,1H,-CH2-C H -CH2-),3.86(s,3H,-OC H 3),3.79(s,3H,-OC H 3),3.23–3.35(m,2H),3.12–3.22(m,2H),3.02–3.10(m,2H),2.83–2.93(m,2H),2.26(s,12H,4×-C H 3). 13 C NMR (100MHz, CDCl3): δ=156.8,156.6,156.5,155.3,138.9,138.8,137.0,136.9,132.5,131.6,130.6,130.2,129.9,129 .8,129.3,129.1,129.0,127.7,127.5,127.3,124.2,111.4,110.1,81.8,80.5,55.7,55.4,40.2,39.6,35.9,19.8,19.7.

[0043] 3) High-resolution mass spectrometric characteristics of the compound:

[0044] Using electrospray ionization: calcd for C 38 H 40 N2O4Na + ,([M+Na] + )611.2886, found 611.2883.

[0045] The physicochemical properties of compound Ⅰ-4 are as follows:

[0046] 1) White solid, melting point 76.7–77.6°C;

[0047] 2) NMR spectrum characteristics of the compound:

[0048] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ = 7.60 (s, 1H, Ar-H), 7.58 (s, 2H, Ar-H), 7.56 (s, 1H, Ar-H), 7.38–7.41 (m,2H,Ar-H),7.24(s,2H,Ar-H),7.23(s,2H,Ar-H),7.19(d,J=8.0Hz,2H,Ar-H),6.92(s,1H Ar-H),6.90(s,1HAr-H),5.04–5.12(m,1H,-CH2-C H -CH2-),4.93–5.01(m,1H,-CH2-C H -CH2-),3.86(s,3H,-OC H 3),3.79(s,3H,-OC H 3),3.24–3.36(m,2H),3.03–3.21(m,4H),2.83–2.93(m,4H),1.25(d,J=7.2Hz,12H,4×-CH-C H 3). 13 C NMR (100MHz, CDCl3): δ=157.1,156.8,156.7,155.6,151.4,151.3,132.8,131.9,130.9,130.6,129.6,129 .4,129.3,127.9,127.6,127.0,125.2,111.7,110.4,82.2,80.8,56.0,55.7,40.5,39.9,36.2,34.4,24.1.

[0049] 3) High-resolution mass spectrometric characteristics of the compound:

[0050] Using electrospray ionization: calcd for C 40 H 45 N2O4 + ,([M+H] + )617.3379, found 617.3384.

[0051] The physicochemical properties of compound Ⅰ-5 are as follows:

[0052] 1) White solid, melting point 83.4–84.2°C;

[0053] 2) NMR spectrum characteristics of the compound:

[0054] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ=7.61(s,1H,Ar-H),7.59(s,2H,Ar-H),7.57(s,1H,Ar-H),7.41(s,3H,Ar-H),7.39(s,3H,Ar -H),7.19(d,J=8.0Hz,2H,Ar-H),6.93(d,J=2.0Hz,1H,Ar-H),6.91(d,J=2.4Hz,1H,Ar-H),5.04–5.12(m,1H,-CH2-C H -CH2-),4.93–5.01(m,1H,-CH2-C H -CH2-),3.86(s,3H,-OC H 3),3.79(s,3H,-OC H 3),3.25–3.37(m,2H),3.03–3.23(m,4H),2.84–2.93(m,2H),1.32(s,18H,6×-CC H 3). 13 C NMR (100MHz, CDCl3): δ=157.1,156.7,156.6,155.6,153.7,153.6,132.8,131.9,130.9,130.6,129.6,129.4,129 .3,127.5,127.2,126.8,125.9,125.8,125.2,111.7,110.4,82.2,80.9,56.0,55.7,40.5,39.8,36.2,35.2,31.5.

[0055] 3) High-resolution mass spectrometric characteristics of the compound:

[0056] Using electrospray ionization: calcd for C 42 H 49 N2O4 + ,([M+H] + )645.3692, found 645.3689.

[0057] The physicochemical properties of compound Ⅰ-6 are as follows:

[0058] 1) Pale yellow solid, melting point 86.4–87.1°C;

[0059] 2) NMR spectrum characteristics of the compound:

[0060] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ=7.94–7.98(m,2H,Ar-H),7.86(d,J=8.0Hz,2H,Ar-H),7.81(d,J=7.6Hz ,6H,Ar-H),7.46–7.50(m,4H,Ar-H),7.42(s,2H,Ar-H),7.22(d,J=8.4Hz,2H,Ar-H),6.93(s,1H Ar-H),6.91(s,1HAr-H),5.12–5.20(m,1H,-CH2-C H -CH2-),5.00–5.08(m,1H,-CH2-C H -CH2-),3.87(s,3H,-OC H 3),3.79(s,3H,-OC H 3),3.36–3.47(m,2H),3.14–3.28(m,4H),2.89–2.98(m,2H). 13 CNMR (100MHz, CDCl3): δ=157.1,157.0,156.9,155.7,134.3,134.2,133.3 ,133.2,132.8,131.9,130.9,130.6,129.5,129.4,129.3,128.8,128.7,1 28.6,128.5,128.1,127.9,127.7,127.3,127.2,127.1,127.0,126.9,125 .1,123.9,123.8,111.8,110.4,82.5,81.2,56.0,55.7,40.6,39.7,36.2.

[0061] 3) High-resolution mass spectrometric characteristics of the compound:

[0062] Using electrospray ionization: calcd for C 42 H 36 N2O4Na + ,([M+Na] + )655.2573, found 655.2562.

[0063] The physicochemical properties of compound Ⅰ-7 are as follows:

[0064] 1) White solid, melting point 85.8–86.3°C;

[0065] 2) NMR spectrum characteristics of the compound:

[0066] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ = 7.89–7.93 (m, 2H, Ar-H), 7.87 (d, J = 5.2Hz, 2H, Ar-H), 7.66 (d, J = 7.6Hz, 2H, Ar-H), 7.48–7.52 (m, 2H, Ar-H), 7.42 (d, J = 8. 4Hz,1H,Ar-H),7.38(s,1H,Ar-H),7.20(d,J=8.8Hz,2H,Ar-H),6.94(d,J=2.4Hz,1H,Ar-H),6.92(d,J=2.0Hz,1H,Ar-H),5.12–5.20(m,1H,-CH2-C H -CH2-),5.02–5.10(m,1H,-CH2-C H -CH2-),3.88(s,3H,-OC H 3),3.80(s,3H,-OC H 3),3.26–3.37(m,2H),3.04–3.23(m,4H),2.90–2.98(m,2H). 13 C NMR (100MHz, CDCl3): δ=157.1,155.7,155.2,155.1,133.4,133.3,132.8,131.9,131.7,131.5,130.9,130.8,130.5,130. 3,129.9,129.6,129.4,129.0,124.7,118.5,118.4,113.4,113.3,111.8,110.5,83.1,81.9,56.0,55.8,40.4,39.1,36.1.

[0067] 3) High-resolution mass spectrometric characteristics of the compound:

[0068] Using electrospray ionization: calcd for C 36 H 31 N4O4 + ,([M+H] + )583.2345, found 583.2350.

[0069] The physicochemical properties of compound Ⅰ-8 are as follows:

[0070] 1) White solid, melting point 84.1–84.9°C;

[0071] 2) NMR spectrum characteristics of the compound:

[0072] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ=7.70(d,J=2.0Hz,1H,Ar-H),7.67–7.68(m,1H,Ar-H),7.49–7.52(m,1H,Ar-H),7.45–7.47(m,2H,Ar-H),7.39–7.43(m,2H) ,Ar-H),7.36–7.37(m,1H,Ar-H),7.19(d,J=7.2Hz,2H,Ar-H),6.93(d,J=2.0Hz,1H,Ar-H),6.91(d,J=2.4Hz,1H,Ar-H),5.09–5.17(m,1H,-CH2-C H -CH2-),4.99–5.07(m,1H,-CH2-C H -CH2-),3.87(s,3H,-OC H 3),3.80(s,3H,-OC H 3),3.23–3.33(m,2H),3.11–3.21(m,2H),2.99–3.09(m,2H),2.87–2.96(m,2H). 13 C NMR (100MHz, CDCl3): δ=157.1,155.7,155.1,155.0,134.3,134.2,133.3,133.2,132.8,131.9,131.0,130.9,130.5,1 30.3,130.1,129.5,129.4,129.1,128.7,126.0,124.8,111.7,110.4,82.9,81.7,56.0,55.8,40.4,39.3,36.1,27.2.

[0073] 3) High-resolution mass spectrometric characteristics of the compound:

[0074] Using electrospray ionization: calcd for C 34 H 28 N2O4Na 35 Cl4 + ,([M+Na] + )691.0701,found691.0693.

[0075] The physicochemical properties of compound Ⅰ-9 are as follows:

[0076] 1) White solid, melting point 73.6–74.2°C;

[0077] 2) NMR spectrum characteristics of the compound:

[0078] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.31-7.42 (m, 8H, Ar-H), 7.19 (d, J = 6.8Hz, 2H, Ar-H), 7.05-7.10 (m, 2H,Ar-H),6.93(d,J=1.6Hz,1H,Ar-H),6.91(d,J=2.4Hz,1H,Ar-H),5.08–5.16(m,1H,-CH2-C H -CH2-),4.98–5.05(m,1H,-CH2-C H -CH2-),3.87(s,3H,-OC H 3),3.79(s,3H,-OC H 3),3.23–3.35(m,2H),3.13–3.22(m,2H),3.02–3.11(m,2H),2.87–2.96(m,2H). 13 C NMR (100MHz, CDCl3): δ = 164.0 (d, J CF =245Hz),156.8,155.7(d,J CCCCF =3Hz),155.6(d,J CCCCF =3Hz),155.4,132.5,132.2(d,J CCCF =8Hz),131.9(d,J CCCF =8Hz),131.6,130.6,130.3,130.2,130.1,130.0,129.2,129.0,124.6,122.4,122.3,117.0(d,J CCF =21Hz),116.9(d,J CCF =21Hz),113.5(d,J CCF =23Hz),111.4,110.1,82.4,81.1,55.7,55.4,40.2,39.2,35.8,29.7.

[0079] 3) High-resolution mass spectrometric characteristics of the compound:

[0080] Using electrospray ionization: calcd for C 34 H 31 N2O4F2 + ,([M+H] + )569.2252, found 569.2258.

[0081] The physicochemical properties of compound Ⅰ-10 are as follows:

[0082] 1) White solid, melting point 81.2–81.6°C;

[0083] 2) NMR spectrum characteristics of the compound:

[0084] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (600MHz, CDCl3): δ = 7.59 (s, 1H, Ar-H), 7.57 (s, 2H, Ar-H), 7.56 (s, 1H, Ar-H), 7.40-7.42 (m, 1H, Ar-H), 7.37-7.38 (m, 1H, Ar-H), 7.35 (d, J = 2.4Hz, 2H, Ar-H), 7.34 (d, J = 2.4Hz, 2H, Ar-H), 7.19 (d, J = 8.4Hz, 2H, Ar-H), 6.93 (d ,J=3.6Hz,1H,Ar-H),6.91(d,J=2.8Hz,1H,Ar-H),5.08–5.14(m,1H,-CH2-C H -CH2-),4.98–5.03(m,1H,-CH2-C H -CH2-),3.86(s,3H,-OC H 3),3.79(s,3H,-OC H 3),3.24–3.34(m,2H),3.11–3.21(m,2H),3.02–3.10(m,2H),2.87–2.95(m,2H). 13 C NMR (150MHz, CDCl3): δ=157.1,156.0,155.9,155.7,136.2,136.1,132.8,131.9,131.8,130.9,130. 5,129.5,129.3,129.2,128.8,128.5,128.2,111.7,110.4,82.6,81.3,56.0,55.7,40.539.6,36.2.

[0085] 3) High-resolution mass spectrometric characteristics of the compound:

[0086] Using electrospray ionization: calcd for C 34 H 30 N2O4 35 Cl2Na + ,([M+Na] + )623.1480,found623.1478.

[0087] The physicochemical properties of compound Ⅰ-11 are as follows:

[0088] 1) White solid, melting point 86.4–87.1°C;

[0089] 2) NMR spectrum characteristics of the compound:

[0090] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.51(s,4H,Ar-H),7.50(s,4H,Ar-H),7.39–7.42(m,1H,Ar-H),7.36–7.37(m,1H,Ar-H) ,7.19(d,J=7.2Hz,2H,Ar-H),6.93(d,J=1.6Hz,1H,Ar-H),6.91(d,J=2.0Hz,1H,Ar-H),5.07–5.15(m,1H,-CH2-C H -CH2-),4.96–5.04(m,1H,-CH2-C H -CH2-),3.86(s,3H,-OC H 3),3.79(s,3H,-OC H 3),3.23–3.35(m,2H),3.01–3.22(m,4H),2.86–2.96(m,2H). 13 C NMR (100MHz, CDCl3): δ=156.8,155.7,155.6,155.3,132.4,131.9,131.8,131.6,130.6,130.2,129.2,129.0, 128.9,128.7,128.1,124.6,124.2,124.1,111.4,110.1,99.3,82.3,81.0,55.7,55.4,40.2,39.2,35.8,29.7.

[0091] 3) High-resolution mass spectrometric characteristics of the compound:

[0092] Using electrospray ionization: calcd for C 34 H 31 N2O4 79 Br2 + ,([M+H] + )689.0651,found689.0657.

[0093] The physicochemical properties of compound II-1 are as follows:

[0094] 1) White solid, melting point 74.4–75.2°C;

[0095] 2) NMR spectrum characteristics of the compound:

[0096] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.63–7.65(m,4H,Ar-H),7.36–7.38(m,6H,Ar-H),7.23( d,J=2.0Hz,1H,Ar-H),7.21(d,J=2.0Hz,1H,Ar-H),7.12(s,2H,Ar-H),6.93(s,1H Ar-H),6.91(s,1H Ar-H),4.94–5.02(m,2H,2×-CH2-C H -CH2-),3.74(s,6H,2×-OC H 3),3.34(dd,J=10.0,16.4Hz,2H),3.05–3.15(m,4H),2.83–2.88(m,2H). 13 C NMR (100MHz, CDCl3): δ=156.4,155.8,132.4,129.9,129.7,129.5,128.6,128.5,127.6,127.6,126.6,111.3,82.0,55.8,40.1,39.3.

[0097] 3) High-resolution mass spectrometric characteristics of the compound:

[0098] Using electrospray ionization: calcd for C 34 H 33 N2O4 + ,([M+H] + )533.2440, found 533.2441.

[0099] Figure 1 and Figure 2 They are the hydrogen and carbon nuclear magnetic resonance spectra of compound Ⅱ-1 respectively.

[0100] The physicochemical properties of compound II-2 are as follows:

[0101] 1) White solid, melting point 86.5–86.9°C;

[0102] 2) NMR spectrum characteristics of the compound:

[0103] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ = 7.54 (s, 2H, Ar-H), 7.52 (s, 2H, Ar-H), 7.23 (d, J = 2.4Hz, 1H, Ar-H), 7.21 (d, J = 2.4Hz, 1H, Ar-H), 7.19 (s,2H,Ar-H),7.17(s,2H,Ar-H),7.11(t,J=1.6Hz,2H,Ar-H),6.93(s,1HAr-H),6.91(s,1HAr-H),4.92–5.00(m,2H,2×-CH2-C H -CH2-),3.75(s,6H,2×-OC H 3),3.35(dd,J=10.0,16.4Hz,2H),3.04–3.15(m,4H),2.81–2.87(m,2H),2.36(s,6H,2×-C H 3). 13 C NMR (100MHz, CDCl3): δ=156.8,156.2,140.5,132.7,129.8,129.7,128.9,127.9,127.3,126.9,111.7,82.2,56.1,40.5,39.8,21.7.

[0104] 3) High-resolution mass spectrometric characteristics of the compound:

[0105] Using electrospray ionization: calcd for C 36 H 36 N2O4Na + ,([M+Na] + )583.2573, found 583.2570.

[0106] The physicochemical properties of compound II-3 are as follows:

[0107] 1) White solid, melting point 80.2–80.6°C;

[0108] 2) NMR spectrum characteristics of the compound:

[0109] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ = 7.45 (s, 2H, Ar-H), 7.36 (s, 1H, Ar-H), 7.34 (s, 1H, Ar-H), 7.22 (d, J = 1 .2Hz,1H,Ar-H),7.20(d,J=1.2Hz,1H,Ar-H),7.14(s,1H,Ar-H),7.12(s,3H,Ar-H),6.93(s,1H Ar-H),6.91(s,1HAr-H),4.91–4.99(m,2H,2×-CH2-C H -CH2-),3.75(s,6H,2×-OC H 3),3.34(dd,J=10.0,16.4Hz,2H),3.03–3.15(m,4H),2.81–2.86(m,2H),2.26(s,12H,4×-C H 3). 13 C NMR (100MHz, CDCl3): δ=156.5,155.9,138.9,136.9,132.5,129.9,129.5,12 8.7,127.7,127.6,127.3,124.2,111.4,81.9,55.8,40.2,39.6,19.7,19.6.

[0110] 3) High-resolution mass spectrometric characteristics of the compound:

[0111] Using electrospray ionization: calcd for C 38 H 40 N2O4Na + ,([M+Na] + )611.2886, found 611.2883.

[0112] The physicochemical properties of compound II-4 are as follows:

[0113] 1) White solid, melting point 72.0–72.6°C;

[0114] 2) NMR spectrum characteristics of the compound:

[0115] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ=7.59(s,2H,Ar-H),7.57(s,2H,Ar-H),7.25(s,2H,Ar-H),7.23(s,2H,Ar-H),7.20(s,2H,Ar-H),7.13(s,2H,Ar-H),6.93(s,1H Ar-H),6.91(s,1H Ar-H),4.93–5.01(m,2H,2×-CH2-C H -CH2-),3.75(s,6H,2×-OC H 3),3.36(dd,J=10.4,16.8Hz,2H),3.05–3.15(m,4H),2.81–2.95(m,4H),1.25(d,J=10.8Hz,12H,4×-CH-C H 3). 13 C NMR (100MHz, CDCl3): δ=156.7,156.2,151.4,132.8,129.8,129.0,127.9,127.7,127.1,127.0,111.7,82.2,56.1,40.5,39.8,34.4,24.1.

[0116] 3) High-resolution mass spectrometric characteristics of the compound:

[0117] Using electrospray ionization: calcd for C 40 H 45 N2O4 + ,([M+H] + )617.3379, found 617.3384.

[0118] The physicochemical properties of compound II-5 are as follows:

[0119] 1) White solid, melting point 78.3–78.7°C;

[0120] 2) NMR spectrum characteristics of the compound:

[0121] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ = 7.60 (s, 2H, Ar-H), 7.58 (s, 2H, Ar-H), 7.41 (s, 2H, Ar-H), 7.40 (s, 2H, Ar-H),7.23(d,J=2.0Hz,1H,Ar-H),7.20(d,J=2.0Hz,1H,Ar-H),7.13(s,2H,Ar-H),6.93(s,1H Ar-H),6.91(s,1HAr-H),4.93–5.01(m,2H,2×-CH2-C H -CH2-),3.75(s,6H,2×-OC H 3),3.37(dd,J=10.4,16.8Hz,2H),3.05–3.15(m,4H),2.81–2.87(m,2H),1.32(s,18H,6×-CC H 3). 13 C NMR (100MHz, CDCl3): δ=156.6,156.2,153.7,132.8,129.8,129.0,128.0,127.3,126.8,126.0,111.7,82.2,56.1,40.5,39.8,35.2,31.5.

[0122] 3) High-resolution mass spectrometric characteristics of the compound:

[0123] Using electrospray ionization: calcd for C 42 H 49 N2O4 + ,([M+H] + )645.3692, found 645.3694.

[0124] The physicochemical properties of compound II-6 are as follows:

[0125] 1) Pale yellow solid, melting point 83.6–84.3°C;

[0126] 2) NMR spectrum characteristics of the compound:

[0127] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ=7.96(s,1H,Ar-H),7.94(s,1H,Ar-H),7.84(s,2H,Ar-H),7.81(s,3H,Ar-H),7.79(s,3H,Ar-H),7.45–7.50 (m,4H,Ar-H),7.23–7.24(m,2H,Ar-H),7.15(d,J=1.6Hz,2H,Ar-H),6.94(s,1HAr-H),6.92(s,1HAr-H),5.00–5.07(m,2H,2×-CH2-C H -CH2-),3.75(s,6H,2×-OC H 3),3.47(dd,J=10.0,16.4Hz,2H),3.12–3.22(m,4H),2.86–2.91(m,2H). 13 C NMR (100MHz, CDCl3): δ=156.9,156.2,134.3,133.3,132.8,129.9,128.9,128.8, 128.6,128.0,127.7,127.3,127.1,127.0,123.9,111.7,82.5,56.1,40.5,39.7.

[0128] 3) High-resolution mass spectrometric characteristics of the compound:

[0129] Using electrospray ionization: calcd for C 42 H 36 N2O4Na + ,([M+H] + )655.2573, found 655.2568.

[0130] The physicochemical properties of compound II-7 are as follows:

[0131] 1) White solid, melting point 84.1–84.8°C;

[0132] 2) NMR spectrum characteristics of the compound:

[0133] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ=7.92(s,1H,Ar-H),7.90(s,1H,Ar-H),7.86(s,2H,Ar-H),7.66(s,1H,Ar-H),7.65(s,1H,Ar-H),7.50(t,J=7.6Hz,2H,Ar -H),7.23(d,J=1.6Hz,1H,Ar-H),7.21(d,J=1.6Hz,1H,Ar-H),7.12(s,2H,Ar-H),6.94(s,1HAr-H),6.92(s,1HAr-H),5.02–5.10(m,2H,2×-CH2-C H -CH2-),3.75(s,6H,2×-OC H 3),3.78(dd,J=10.4,16.4Hz,2H),3.06–3.14(m,4H),2.93(dd,J=6.8,14.0Hz,2H). 13 CNMR (100MHz, CDCl3): δ=156.3,155.1,133.3,132.8,132.7,131.6,130.8,130.3 ,129.9,129.8,128.4,128.0,118.4,113.4,111.7,83.1,83.0,56.1,40.4,39.1.

[0134] 3) High-resolution mass spectrometric characteristics of the compound:

[0135] Using electrospray ionization: calcd for C 34 H 31 N2O4 79 Br2 + ,([M+H] + )583.2345,found583.2347.

[0136] The physicochemical properties of compound II-8 are as follows:

[0137] 1) White solid, melting point 82.4-82.8℃;

[0138] 2) NMR spectrum characteristics of the compound:

[0139] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ=7.68(d,J=1.2Hz,2H,Ar-H),7.50(d,J=1.6Hz,1H,Ar-H),7.48(d,J=1.6Hz,1H,Ar-H),7.45(s,1H,Ar-H),7.43(s,1H,Ar -H),7.22(d,J=2.0Hz,1H,Ar-H),7.20(d,J=2.0Hz,1H,Ar-H),7.11(s,2H,Ar-H),6.93(s,1HAr-H),6.91(s,1HAr-H),4.99–5.06(m,2H,2×-CH2-C H -CH2-),3.75(s,6H,2×-OC H 3),3.33(dd,J=10.4,16.4Hz,2H),3.08–3.13(m,2H),3.01–3.07(m,2H). 13 C NMR (100MHz, CDCl3): δ=156.0,154.7,133.9,133.0,132.4,130.7,129.8,12 9.6,129.5,128.3,128.2,127.6,125.6,111.4,82.6,55.8,40.1,39.0,29.7.

[0140] 3) High-resolution mass spectrometric characteristics of the compound:

[0141] Using electrospray ionization: calcd for C 34 H 29 N2O4 35 Cl4 + ,([M+H] + )669.0881,found669.0881.

[0142] The physicochemical properties of compound II-9 are as follows:

[0143] 1) White solid, melting point 73.4–74.2°C;

[0144] 2) NMR spectrum characteristics of the compound:

[0145] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ = 7.31–5.40 (m, 6H, Ar-H), 7.23 (d, J = 2.4Hz, 1H, Ar-H), 7.21 (d, J = 2.0Hz, 1H, Ar-H), 7.1 1–7.12(m,2H,Ar-H),7.05–7.10(m,2H,Ar-H),6.93(s,1HAr-H),6.91(s,1HAr-H),4.97–5.05(m,2H,2×-CH2-C H -CH2-),3.75(s,6H,2×-OCH3),3.35(dd,J=10.0,16.4Hz,2H),3.03–3.14(m,4H),2.85–2.90(m,2H). 13 C NMR (100MHz, CDCl3): δ = 164.0 (d, J CF =245Hz),155.9,155.6(d,J CCCCF =3Hz),132.4,132.0(d,J CCCF =8Hz),130.3(d,J CCCF =8Hz),129.5,128.3,127.6,122.4(d,J CCCCF =3Hz),117.0(d,J CCF =21Hz),113.5(d,J CCF =23Hz),111.4,82.4,55.8,40.1,39.2,29.7.

[0146] 3) High-resolution mass spectrometric characteristics of the compound:

[0147] Using electrospray ionization: calcd for C 34 H 31 N2O4F2 + ,([M+H] + )569.2252, found 569.2258.

[0148] The physicochemical properties of compound II-10 are as follows:

[0149] 1) White solid, melting point 75.5–76.1°C;

[0150] 2) NMR spectrum characteristics of the compound:

[0151] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (600MHz, CDCl3): δ=7.58(s,2H,Ar-H),7.56(s,2H,Ar-H),7.36(s,2H,Ar-H),7.34(s,2H, Ar-H),7.22(d,J=2.4Hz,1H,Ar-H),7.21(d,J=2.4Hz,1H,Ar-H),7.11(s,2H,Ar-H),6.93(s,1H Ar-H),6.91(s,1HAr-H),4.97–5.03(m,2H,2×-CH2-C H -CH2-),3.75(s,6H,2×-OC H 3),3.29–3.34(m,2H),3.10–3.13(m,2H),3.04–3.08(m,2H),2.85–2.88(m,2H). 13 C NMR (150MHz, CDCl3): δ=156.2,155.9,136.2,132.7,129.9,129.3,128.7,128.6,128.2,127.9,111.7,82.7,56.1,40.5,39.6.

[0152] 3) High-resolution mass spectrometric characteristics of the compound:

[0153] Using electrospray ionization: calcd for C 34 H 30 N2O4 35 Cl2Na + ,([M+Na] + )623.1480,found623.1481.

[0154] The physicochemical properties of compound II-11 are as follows:

[0155] 1) White solid, melting point 83.4–84.1°C;

[0156] 2) NMR spectrum characteristics of the compound:

[0157] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.50 (s, 8H, Ar-H), 7.22 (d, J = 2.0Hz, 1H, Ar-H), 7.20 (d, J = 2.0Hz, 1H, Ar-H), 7.11 (d, J = 2.0Hz, 2H, Ar-H), 6.93 (s, 1H Ar-H),6.91(s,1H Ar-H),4.96–5.04(m,2H,2×-CH2-C H-CH2-),3.75(s,6H,2×-OC H 3),3.28–3.39(m,2H),3.03–3.14(m,4H),2.89(dd,J=6.8,14.0Hz,2H). 13 C NMR (100MHz, CDCl3): δ=155.9,155.7,154.3,138.4,132.4,131.9,131.7,129.5,128.7,1 28.4,128.1,127.6,124.2,121.3,115.2,111.3,82.4,55.8,41.6,40.2,39.2,29.7,13.9.

[0158] 3) High-resolution mass spectrometric characteristics of the compound:

[0159] Using electrospray ionization: calcd for C 34 H 31 N2O4 79 Br2 + ,([M+H] + )689.0651,found689.0660.

[0160] The physicochemical properties of compound III-1 are as follows:

[0161] 1) White solid, melting point 78.7–79.5°C;

[0162] 2) NMR spectrum characteristics of the compound:

[0163] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.59–7.64(m,4H,Ar-H),7.35–7.38(m,6H,Ar-H),7.22(s,1H ,Ar-H),7.20(dd,J=2.4,8.4Hz,1H,Ar-H),7.10(d,J=6.8Hz,2H,Ar-H),7.05(s,1H,-O H ),6.97(d,J=8.0Hz,1H,Ar-H),6.92(d,J=8.8Hz,1H,Ar-H),5.46(s,1H,-O H ),5.07–5.15(m,1H,-CH2-C H -CH2-),4.93–5.01(m,1H,-CH2-C H-CH2-),3.31–3.45(m,2H),3.01–3.21(m,5H),2.88(dd,J=6.8,14.4Hz,1H). 13 C NMR (100MHz, CDCl3): δ=158.2,157.1,155.1,151.8,132.7,131.4,130.7,130.5,129.8,129.7,129.6,129.4,1 29.3,129.2,129.0,128.2,129.1,127.0,124.3,117.7,116.3,82.4,81.9,40.5,39.8,39.7,36.5,27.2,23.0.

[0164] 3) High-resolution mass spectrometric characteristics of the compound:

[0165] Using electrospray ionization: calcd for C 32 H 28 N2O4Na + ,([M+Na] + )527.1947, found 527.1949.

[0166] The physicochemical properties of compound III-2 are as follows:

[0167] 1) White solid, melting point 83.0–83.6°C;

[0168] 2) NMR spectrum characteristics of the compound:

[0169] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.49–7.54(m,4H,Ar-H),7.21(s,2H,Ar-H),7.16–7.19(m,4H,Ar-H),7.10(d, J=8.8Hz,2H,Ar-H),6.99(d,J=7.6Hz,1H,Ar-H),6.92(d,J=8.0Hz,1H,Ar-H),5.06–5.13(m,1H,-CH2-C H -CH2-),4.91–4.99(m,1H,-CH2-C H -CH2-),3.30–3.45(m,2H),3.02–3.19(m,5H),2.87(dd,J=6.8,14.0Hz,1H),2.36(s,3H,-C H 3),2.35(s,3H,-C H 3). 13C NMR (100MHz, CDCl3): δ=158.3,157.0,155.2,151.8,141.0,140.7,132.7,131.3,129.7,129.6,129.3,1 29.2,128.2,127.1,126.9,126.4,124.4,117.9,116.3,82.2,81.8,40.5,39.9,39.8,36.6,27.2,21.8.

[0170] 3) High-resolution mass spectrometric characteristics of the compound:

[0171] Using electrospray ionization: calcd for C 34 H 32 N2O4Na + ,([M+Na] + )555.2260, found 555.2267.

[0172] The physicochemical properties of compound III-3 are as follows:

[0173] 1) Pale yellow solid, melting point 86.9–87.5°C;

[0174] 2) NMR spectrum characteristics of the compound:

[0175] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.43(s,1H,Ar-H),7.41(s,1H,Ar-H),7.30–7.35(m,3H,Ar-H),7.22(s,1H,-OH),7.20(dd,J=2.0,8.4Hz,1H,Ar-H),7.14(d ,J=7.6Hz,2H,Ar-H),7.08–7.10(m,2H,Ar-H),6.98(d,J=8.4Hz,1H,Ar-H),6.92(d,J=8.8Hz,1H,Ar-H),5.59(s,1H,-OH),5.05–5.12(m,1H,-CH2-C H -CH2-),4.90–4.98(m,1H,-CH2-C H -CH2-),3.30–3.42(m,2H),3.02–3.18(m,5H),2.85(dd,J=6.8,14.0Hz,1H),2.23–2.26(m,12H,4×-CH3). 13C NMR (100MHz, CDCl3): δ=158.4,157.1,155.2,151.8,139.8,139.4,137.4,137.3,132.7,131.3,130.2,129.8,129.6,129.3,128.2 ,128.1,128.0,127.3,126.7,124.7,124.5,124.4,118.0,116.3,82.1,81.8,40.5,39.9,39.8,36.7,31.9,27.2,20.2,20.1,20.0.

[0176] 3) High-resolution mass spectrometric characteristics of the compound:

[0177] Using electrospray ionization: calcd for C 36 H 36 N2O4Na + ,([M+Na] + )583.2573, found 583.2575.

[0178] The physicochemical properties of compound III-4 are as follows:

[0179] 1) Yellow solid, melting point 89.5–90.3°C;

[0180] 2) NMR spectrum characteristics of the compound:

[0181] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.53–7.58(m,4H,Ar-H),7.21–7.24(m,6H,Ar-H),7.18(s,1H,-O H ),7.09(d,J=6.8Hz,2H,Ar-H),6.98(d,J=8.0Hz,1H,Ar-H),6.91(d,J=8.4Hz,1H,Ar-H),5.54(s,1H,-O H ),5.05–5.13(m,1H,-CH2-C H -CH2-),4.91–4.99(m,1H,-CH2-C H -CH2-),3.30–3.43(m,2H),3.02–3.19(m,5H),2.81–2.94(m,3H),1.22–1.25(m,12H,4×-CH-C H 3). 13C NMR (100MHz, CDCl3): δ=158.2,156.9,155.2,151.9,151.8,151.6,132.7,131.4,129.8,129.6,129.4,129.3,128.3, 127.4,127.2,127.1,127.0,126.9,124.5,118.0,116.3,82.2,81.9,40.5,40.0,39.9,36.6,34.4,30.0,24.1,24.0.

[0182] 3) High-resolution mass spectrometric characteristics of the compound:

[0183] Using electrospray ionization: calcd for C 38 H 40 N2O4Na + ,([M+Na] + )611.2886, found 611.2878.

[0184] The physicochemical properties of compound III-5 are as follows:

[0185] 1) Pale yellow solid, melting point 98.6–99.4°C;

[0186] 2) NMR spectrum characteristics of the compound:

[0187] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.54–7.59(m,4H,Ar-H),7.37–7.41(m,4H,Ar-H),7.23(s,1H,-OH),7.21(s,1H,Ar-H),7.19(s,1H,Ar-H) ,7.09(d,J=7.2Hz,2H,Ar-H),6.98(d,J=8.0Hz,1H,Ar-H),6.91(d,J=8.4Hz,1H,Ar-H),5.52(s,1H,-OH),5.06–5.13(m,1H,-CH2-C H -CH2-),4.91–4.99(m,1H,-CH2-C H -CH2-),3.31–3.44(m,2H),3.03–3.20(m,5H),2.81–2.86(m,1H),1.31(s,9H,3×-C-CH3),1.30(s,9H,3×-C-CH3). 13C NMR (100MHz, CDCl3): δ=158.2,156.9,155.3,154.2,153.8,151.9,132.7,131.4,129.8,129.6,129.4,129.3,128.3, 127.0,126.9,126.8,126.5,126.0,125.9,124.5,118.0,116.3,82.2,81.9,40.5,39.9,39.8,36.6,35.2,31.5,31.4.

[0188] 3) High-resolution mass spectrometric characteristics of the compound:

[0189] Using electrospray ionization: calcd for C 40 H 44 N2O4Na + ,([M+Na] + )639.3199, found 639.3191.

[0190] The physicochemical properties of compound III-6 are as follows:

[0191] 1) White solid, melting point 98.9–99.8°C;

[0192] 2) NMR spectrum characteristics of the compound:

[0193] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.95 (d, J = 8.8Hz, 1H, Ar-H), 7.89 (d, J = 8.4Hz, 1H, Ar-H), 7.84 (s, 2H, Ar-H), 7.79–7.82 (m, 6H, Ar-H), 7.47–7.52 (m, 4H, Ar-H), 7.20–7.24(m,2H,Ar-H),7.10–7.14(m,2H,Ar-H),7.00(d,J=8.4Hz,1H,Ar- H),6.94(d,J=8.4Hz,1H,Ar-H),5.32(s,1H,-OH),5.12–5.19(m,1H,-CH2-C H -CH2-),4.98–5.05(m,1H,-CH2-C H -CH2-),3.41–3.56(m,2H),3.25–3.31(m,1H),3.05–3.20(m,4H),2.91(dd,J=6.8,14.4Hz,1H). 13C NMR (100MHz, CDCl3): δ=158.1,156.8,154.9,151.5,134.1,134.0,132.9,132.8,132.4,131.0,129.6,129.3,129.2,129.0,128.9,128.6,128. 5,128.4,128.3,127.9,127.8,127.2,127.1,127.0,126.9,126.7,126. 6,124.1,123.4,117.7,116.0,82.2,81.9,40.2,39.4,39.3,36.3,30.9.

[0194] 3) High-resolution mass spectrometric characteristics of the compound:

[0195] Using electrospray ionization: calcd for C 40 H 32 N2O4Na + ,([M+Na] + )627.2260, found 627.2261.

[0196] The physicochemical properties of compound III-7 are as follows:

[0197] 1) Pale yellow solid, melting point 102.4–102.8°C;

[0198] 2) NMR spectrum characteristics of the compound:

[0199] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.85–7.87(m,3H,Ar-H),7.81(s,1H,Ar-H),7.62–7.65(m,2H,Ar-H),7.51(d,J=7.6Hz,1H,Ar-H),7.47(d,J=8.0H z,1H,Ar-H),7.19(d,J=8.4Hz,1H,Ar-H),7.09(d,J=8.4Hz,2H,Ar-H),6.88–6.93(m,3H,Ar-H),5.72(s,1H,-OH),5.14–5.21(m,1H,-CH2-C H -CH2-),5.00–5.08(m,1H,-CH2-C H -CH2-),3.32–3.41(m,2H),3.16–3.22(m,1H),3.03–3.09(m,4H),2.92(dd,J=6.4,14.0Hz,1H). 13C NMR (100MHz, CDCl3): δ=156.3,155.3,154.7,152.0,133.6,133.4,132.7,131.4,131.3,131.0,130.9,130.5,130.4,1 29.8,129.6,129.5,128.9,128.2,123.9,118.4,118.3,117.3,116.4,113.3,83.1,82.5,40.4,39.2,39.1,36.1,31.3.

[0200] 3) High-resolution mass spectrometric characteristics of the compound:

[0201] Using electrospray ionization: calcd for C 34 H 26 N4O4Na + ,([M+Na] + )577.1852, found 577.1850.

[0202] The physicochemical properties of compound III-8 are as follows:

[0203] 1) Pale yellow solid, melting point 96.6–97.4°C;

[0204] 2) NMR spectrum characteristics of the compound:

[0205] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.68 (s, 1H, Ar-H), 7.67 (s, 1H, Ar-H), 7.43–7.49 (m, 4H, Ar-H), 7.23 (d, J = 8.4Hz, 2H ,Ar-H),7.11(d,J=9.6Hz,2H,Ar-H),6.98(d,J=8.0Hz,1H,Ar-H),6.92(d,J=8.0Hz,1H,Ar-H),6.63(s,1H,-O H ),5.28(s,1H,-O H ),5.13–5.20(m,1H,-CH2-C H -CH2-),4.98–5.06(m,1H,-CH2-C H -CH2-),3.28–3.43(m,2H),2.99–3.17(m,5H),2.86–2.91(m,1H). 13C NMR (100MHz, CDCl3): δ=156.0,154.8,154.6,151.6,134.4,134.1,133.1,133.0,132.4,131.0,130.8,130.7,129.6 ,129.3,129.1,128.7,128.5,128.4,127.8,125.8,125.7,123.8,117.5,116.0,82.6,82.2,40.1,39.0,38.9,36.0.

[0206] 3) High-resolution mass spectrometric characteristics of the compound:

[0207] Using electrospray ionization: calcd for C 32 H 24 N2O4Na 35 Cl4 + ,([M+Na] + )663.0388,found663.0382.

[0208] The physicochemical properties of compound III-9 are as follows:

[0209] 1) White solid, melting point 88.1–88.8°C;

[0210] 2) NMR spectrum characteristics of the compound:

[0211] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.31–7.39(m,6H,Ar-H),7.23(s,1H,Ar-H),7.21(dd,J=2.0,8.0Hz,1H,Ar- H),7.05–7.10(m,4H,Ar-H),6.97(d,J=8.4Hz,1H,Ar-H),6.92(d,J=8.8Hz,1H,Ar-H),6.83(s,1H,-O H ),5.43(s,1H,-O H ),5.10–5.17(m,1H,-CH2-C H -CH2-),4.96–5.04(m,1H,-CH2-C H -CH2-),3.30–3.43(m,2H),3.01–3.19(m,5H),2.90(dd,J=6.4,14.0Hz,1H). 13C NMR (100MHz, CDCl3): δ=164.2,161.8,161.7,157.3,157.2,156.0,154.9,161.8,1 32.6,132.0,131.9,131.5,131.4,131.3,130.7,130.6,130.5,130.4,129.8,129. 5,129.4,129.1,128.1,124.2,122.8,122.7,122.6,117.7,117.6,117.4,117.3,117.1,116.3,113.9,113.8,113.7,113.6,82.6,82.2,40.4,39.5,39.4,36.4,29.9.

[0212] 3) High-resolution mass spectrometric characteristics of the compound:

[0213] Using electrospray ionization: calcd for C 32 H 27 N2O4F2 + ,([M+Na] + )541.1939, found 541.1942.

[0214] The physicochemical properties of compound III-10 are as follows:

[0215] 1) White solid, melting point 73.6–74.2°C;

[0216] 2) NMR spectrum characteristics of the compound:

[0217] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.51–7.56(m,4H,Ar-H),7.32–7.35(m,4H,Ar-H),7.22–7.23(m,1H,Ar-H),7.17–7.20(m,1H,Ar-H),7.08–7.1 0(m,2H,Ar-H),6.96(d,J=8.0Hz,1H,Ar-H),6.91(d,J=8.8Hz,1H,Ar-H),6.84(s,1H,-OH),5.42(s,1H,-OH),5.08–5.16(m,1H,-CH2-C H -CH2-),4.95–5.02(m,1H,-CH2-C H -CH2-),3.29–3.42(m,2H),3.01–3.18(m,5H),2.90(dd,J=6.4,14.4Hz,1H).13 C NMR (100MHz, CDCl3): δ=157.0,155.8,154.6,151.5,136.3,136.0,132.4,131.0,129.6,129.3,129.0,12 8.9,128.8,128.0,127.9,127.8,127.7,127.4,123.9,117.5,116.0,82.3,81.9,40.2,39.3,39.2,36.1.

[0218] 3) High-resolution mass spectrometric characteristics of the compound:

[0219] Using electrospray ionization: calcd for C 32 H 27 N2O4 35 Cl2 + ,([M+Na] + )573.1348,found573.1351.

[0220] The physicochemical properties of compound III-11 are as follows:

[0221] 1) White solid, melting point 94.4–94.9°C;

[0222] 2) NMR spectrum characteristics of the compound:

[0223] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.44–7.51(m,8H,Ar-H),7.22(s,1H,Ar-H),7.16–7.19(m,1H,Ar-H),7.09(d,J=7.2Hz,2H,Ar-H ),6.95(d,J=8.4Hz,1H,Ar-H),6.91(d,J=8.8Hz,1H,Ar-H),6.83(s,1H,-OH),5.44(s,1H,-OH),5.08–5.15(m,1H,-CH2-C H -CH2-),4.94–5.02(m,1H,-CH2-C H -CH2-),3.29–3.41(m,2H),3.00–3.17(m,5H),2.89(dd,J=6.4,14.0Hz,1H). 13C NMR (100MHz, CDCl3): δ=157.4,156.3,154.9,151.8,132.7,132.3,132.2,131.4,129.8,129.6,129.4,129.1 ,128.7,128.5,128.4,128.2,128.1,125.0,124.7,124.2,117.6,116.3,82.6,82.2,40.5,39.6,39.5,36.4.

[0224] 3) High-resolution mass spectrometric characteristics of the compound:

[0225] Using electrospray ionization: calcd for C 32 H 26 N2O4 79 Br2Na + ,([M+Na] + )683.0157,found683.0151.

[0226] The physicochemical properties of compound IV-1 are as follows:

[0227] 1) White solid, melting point 79.0–79.8°C;

[0228] 2) NMR spectrum characteristics of the compound:

[0229] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.59–7.61 (m, 4H, Ar-H), 7.36 (d, J = 5.6Hz, 6H, Ar-H), 7.15 (d, J = 8.0Hz, 4H,Ar-H),6.97(s,1H,Ar-H),6.95(s,1H,Ar-H),6.93(s,2H,2×-OH),4.93–5.00(m,2H,2×-CH2-C H -CH2-),3.38(dd,J=10.016.4Hz,2H),3.02–3.10(m,4H),2.91(dd,J=6.4,14.4Hz,2H). 13 C NMR (100MHz, CDCl3): δ=156.9,151.9,132.3,130.4,130.2,129.5,128.7,126.7,125.3,125.2,117.2,81.9,40.2,39.5,26.9,22.6.

[0230] 3) High-resolution mass spectrometric characteristics of the compound:

[0231] Using electrospray ionization: calcd for C 32 H 28 N2O4Na + ,([M+Na] + )527.1947, found 527.1953.

[0232] The physicochemical properties of compound IV-2 are as follows:

[0233] 1) White solid, melting point 85.2–85.8°C;

[0234] 2) NMR spectrum characteristics of the compound:

[0235] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.50 (d, J = 7.6Hz, 6H, Ar-H), 7.15–7.17 (m, 6H, Ar-H), 7.13 (s, 1H, -OH),7.11(s,1H,-OH),6.98(s,1H,Ar-H),6.96(s,1H,Ar-H),4.90–4.98(m,2H,2×-CH2-C H -CH2-),3.36(dd,J=10.4,16.8Hz,2H),3.01–3.08(m,4H),2.88(dd,J=6.4,14.0Hz,2H),2.34(s,6H,2×-CH3). 13 CNMR (100MHz, CDCl3): δ=157.2,152.2,140.8,132.6,130.7,129.9,129.8,126.9,126.7,125.7,117.6,82.1,40.5,40.0,27.2,21.8.

[0236] 3) High-resolution mass spectrometric characteristics of the compound:

[0237] Using electrospray ionization: calcd for C 34 H 33 N2O4 + ,([M+Na] + )533.2440, found 533.2446.

[0238] The physicochemical properties of compound IV-3 are as follows:

[0239] 1) White solid, melting point 96.4–97.0°C;

[0240] 2) NMR spectrum characteristics of the compound:

[0241] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.40(s,2H,Ar-H),7.32(s,2H,Ar-H),7.30(s,2H,Ar-H),7.16(s,2H,2×-O H ),7.14(s,1H,Ar-H),7.11(s,2H,Ar-H),7.09(s,1H,Ar-H),6.97(s,1H,Ar-H),6.95(s,1H,Ar-H),4.89–4.97(m,2H,2×-CH2-C H -CH2-),3.28–3.35(m,2H),3.01–3.07(m,4H),2.88(dd,J=6.0,14.0Hz,2H),2.24(s,6H,2×-C H 3),2.23(s,6H,2×-C H 3). 13 C NMR (100MHz, CDCl3): δ=157.3,152.3,139.5,137.4,132.6,130.7,130.3,130.0,1 29.9,128.1,127.1,125.6,124.6,117.6,82.0,40.5,40.4,40.1,40.0,20.1,20.0.

[0242] 3) High-resolution mass spectrometric characteristics of the compound:

[0243] Using electrospray ionization: calcd for C 36 H 36 N2O4Na + ,([M+Na] + )583.2573, found 583.2564.

[0244] The physicochemical properties of compound IV-4 are as follows:

[0245] 1) Pale yellow solid, melting point 85.4–86.2°C;

[0246] 2) NMR spectrum characteristics of the compound:

[0247] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ=7.55(s,2H,Ar-H),7.53(s,2H,Ar-H),7.23(s,2H,Ar-H),7.21(s,2H,Ar-H),7.17(s,2H,2×-O H ),7.15(s,2H,Ar-H),7.13(s,2H,Ar-H),6.98(s,1H,Ar-H),6.96(s,1H,Ar-H),4.91–4.99(m,2H,2×-CH2-C H -CH2-),3.38(dd,J=10.4,16.8Hz,2H),3.02–3.09(m,4H),2.84–2.93(m,4H),1.24(d,J=6.8Hz,12H,4×-CH-C H 3). 13 C NMR (100MHz, CDCl3): δ=157.1,152.3,151.7,132.6,130.8,130.0,129.9,127.2,127.1,127.0,125.5,117.6,82.1,40.5,40.0,34.4,24.1.

[0248] 3) High-resolution mass spectrometric characteristics of the compound:

[0249] Using electrospray ionization: calcd for C 38 H 40 N2O4Na + ,([M+Na] + )611.2886, found 611.2878.

[0250] The physicochemical properties of compound IV-5 are as follows:

[0251] 1) Pale yellow solid, melting point 89.8–90.6°C;

[0252] 2) NMR spectrum characteristics of the compound:

[0253] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.56(s,2H,Ar-H),7.54(s,2H,Ar-H),7.39(s,2H,Ar-H),7.37(s,2H,Ar-H),7.17(s,2H,2×-O H),7.15(s,2H,Ar-H),7.13(s,2H,Ar-H),6.98(s,1H,Ar-H),6.96(s,1H,Ar-H),4.92–4.99(m,2H,2×-CH2-C H -CH2-),3.38(dd,J=10.4,16.8Hz,2H),3.02–3.10(m,4H),2.89(dd,J=6.0,14.0Hz,2H),1.30(s,18H,6×-CC H 3). 13 C NMR (100MHz, CDCl3): δ=157.1,153.9,152.3,132.6,130.8,130.0,129.9,126.8,126.0,125.5,117.6,82.1,40.5,40.0,35.2,31.5.

[0254] 3) High-resolution mass spectrometric characteristics of the compound:

[0255] Using electrospray ionization: calcd for C 40 H 44 N2O4Na + ,([M+Na] + )639.3199, found 639.3196.

[0256] The physicochemical properties of compound IV-6 are as follows:

[0257] 1) White solid, melting point 95.9–96.6°C;

[0258] 2) NMR spectrum characteristics of the compound:

[0259] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.89–7.90(m,1H,Ar-H),7.87–7.88(m,1H,Ar-H),7.81(s,2H,2×-OH),7.76–7.79(m,6H,Ar-H),7.43–7.49(m, 4H,Ar-H),7.18(d,J=2.4Hz,3H,Ar-H),7.16(d,J=2.0Hz,1H,Ar-H),6.99(s,1H,Ar-H),6.97(s,1H,Ar-H),4.96–5.04(m,2H,2×-CH2-C H-CH2-),3.43–3.46(m,1H),3.39-3.42(m,1H),3.12–3.18(m,2H),3.08(dd,J=6.4,14.0Hz,2H),2.93(dd,J=6.4,14.0Hz,2H). 13 C NMR (100MHz, CDCl3): δ=157.0,151.9,134.0,132.9,132.3,130.5,129.7,128.6,128.4 ,127.8,127.3,127.1,127.0,126.9,126.7,123.4,117.2,82.1,40.2,40.1,39.4,30.9.

[0260] 3) High-resolution mass spectrometric characteristics of the compound:

[0261] Using electrospray ionization: calcd for C 40 H 32 N2O4Na + ,([M+Na] + )627.2260, found 627.2253.

[0262] The physicochemical properties of compound IV-7 are as follows:

[0263] 1) Pale yellow solid, melting point 100.1–100.8°C;

[0264] 2) NMR spectrum characteristics of the compound:

[0265] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.87(s,1H,Ar-H),7.85(s,1H,Ar-H),7.82(s,2H,Ar-H),7.64(s,1H,Ar-H),7.62(s,1H,Ar-H),7.45–7. 49(m,2H,Ar-H),7.14–7.17(m,4H,Ar-H),6.97(s,2H,2×-OH),6.95(s,1H,Ar-H),6.93(s,1H,Ar-H),5.00–5.08(m,2H,2×-CH2-C H -CH2-),3.39(dd,J=10.4,16.4Hz,2H),3.01–3.10(m,4H),2.96(dd,J=6.0,14.0Hz,2H). 13C NMR (100MHz, CDCl3): δ=155.4,153.2,133.5,132.7,132.6,131.2,130.9,130 .7,130.4,130.0,129.6,125.5,118.4,117.4,113.2,82.9,40.4,39.2,31.3.

[0266] 3) High-resolution mass spectrometric characteristics of the compound:

[0267] Using electrospray ionization: calcd for C 34 H 26 N4O4Na + ,([M+Na] + )577.1852, found 577.1850.

[0268] The physicochemical properties of compound IV-8 are as follows:

[0269] 1) Yellow solid, melting point 97.2–97.9°C;

[0270] 2) NMR spectrum characteristics of the compound:

[0271] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.63 (s, 2H, Ar-H), 7.39–7.44 (m, 4H, Ar-H), 7.14 (d, J = 8. 0Hz,4H,Ar-H),6.93(s,1H,Ar-H),6.91(s,1H,Ar-H),4.95–5.03(m,2H,2×-CH2-C H -CH2-),3.27–3.34(m,2H),2.98–3.04(m,4H),2.87–2.92(m,2H). 13 C NMR (100MHz, CDCl3): δ=155.4,152.2,134.5,133.4,132.6,131.1,130.8,129.8,129.7,128.7,126.0,125.2,117.5,82.8,40.4,39.4.

[0272] 3) High-resolution mass spectrometric characteristics of the compound:

[0273] Using electrospray ionization: calcd for C 32 H 25 N2O4 35 Cl4 + ,([M+H] +)641.0568,found641.0571.

[0274] The physicochemical properties of compound IV-9 are as follows:

[0275] 1) White solid, melting point 83.7–84.5°C;

[0276] 2) NMR spectrum characteristics of the compound:

[0277] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.31–7.37 (m, 6H, Ar-H), 7.16 (d, J = 8.4Hz, 4H, Ar-H), 7.05–7 .09(m,2H,Ar-H),6.96(s,2H,Ar-H),6.94(s,2H,2×-OH),4.96–5.03(m,2H,2×-CH2-C H -CH2-),3.38(dd,J=10.4,16.8Hz,2H),3.01–3.08(m,4H),2.92(dd,J=6.0,14.0Hz,2H). 13 C NMR (100MHz, CDCl3): δ=164.2,161.8,156.4,156.3,152.1,132.6,131.7,131.6,130.8,130.7, 130.6,129.8,125.3,122.8,122.7,117.6,117.5,117.3,113.9,113.7,82.5,40.4,39.6,27.2.

[0278] 3) High-resolution mass spectrometric characteristics of the compound:

[0279] Using electrospray ionization: calcd for C 32 H 26 N2O4F2Na + ,([M+Na] + )563.1758,found563.1765.

[0280] The physicochemical properties of compound IV-10 are as follows:

[0281] 1) White solid, melting point 97.0–97.5°C;

[0282] 2) NMR spectrum characteristics of the compound:

[0283] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (600MHz, CDCl3): δ = 7.52 (d, J = 1.6Hz, 2H, Ar-H), 7.51 (d, J = 1.6Hz, 2H, Ar-H), 7.32 (d, J = 1.2Hz, 2H, Ar-H) ,7.31(d,J=1.2Hz,2H,Ar-H),7.12–7.15(m,4H,Ar-H),6.94(s,1H,Ar-H),6.93(s,1H,Ar-H),6.89(s,2H,2×-O H ),4.94–4.99(m,2H,2×-CH2-C H -CH2-),3.34(dd,J=10.0,16.8Hz,2H),3.00–3.05(m,4H),2.90(dd,J=6.0,14.4Hz,2H). 13 C NMR (150MHz, CDCl3): δ=156.3,152.2,136.5,132.6,130.8,129.9,129.3,128.2,128.1,125.2,117.5,82.4,40.5,40.4,39.7.

[0284] 3) High-resolution mass spectrometric characteristics of the compound:

[0285] Using electrospray ionization: calcd for C 32 H 26 N2O4 35 Cl2Na + ,([M+Na] + )595.1167,found595.1165.

[0286] The physicochemical properties of compound IV-11 are as follows:

[0287] 1) White solid, melting point 92.2–92.7°C;

[0288] 2) NMR spectrum characteristics of the compound:

[0289] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.44–7.49(m,8H,Ar-H),7.15(d,J=7.2Hz,4H,Ar-H),6.95(s,1H,Ar-H),6.93(s,1H,Ar-H),6.81(s,2H,2×-O H ),4.94–5.01(m,2H,2×-CH2-C H-CH2-),3.36(dd,J=10.4,16.8Hz,2H),3.01–3.06(m,4H),2.86–2.92(m,2H). 13 C NMR (100MHz, CDCl3): δ=156.4,152.2,132.6,132.3,130.7,129.8,128.6,128.4,125.4,125.3,124.8,117.5,82.5,40.5,39.6.

[0290] 3) High-resolution mass spectrometric characteristics of the compound:

[0291] Using electrospray ionization: calcd for C 32 H 26 N2O4 79 Br2Na + ,([M+Na] + )683.0157,found683.0152.

[0292] The physicochemical properties of compound V-1 are as follows:

[0293] 1) White solid, melting point 106.3–106.9°C;

[0294] 2) NMR spectrum characteristics of the compound:

[0295] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.93 (d, J = 2.0Hz, 1H, Ar-H), 7.83 (d, J = 2.0Hz, 1H, Ar-H), 7.73 (d, J = 1.2Hz, 1H, Ar-H) ,7.62–7.64(m,4H,Ar-H),7.52(d,J=1.6Hz,1H,Ar-H),7.40(d,J=4.8Hz,6H,Ar-H),5.06–5.12(m,1H,-CH2-C H -CH2-),4.99–5.04(m,1H,-CH2-C H -CH2-),3.98(s,3H,-OC H 3),3.53(s,3H,-OC H 3),3.44–3.51(m,2H),3.00–3.22(m,6H). 13C NMR (100MHz, CDCl3): δ=157.0,156.9,152.0,149.8,145.0,144.1,136.9,136.2,135.0,134.4,134.2,132.4,130 .6,130.5,129.5,129.4,129.1,126.9,125.8,124.9,81.0,80.5,63.1,62.6,54.0,40.5,40.1,35.4,35.3,29.6.

[0296] 3) High-resolution mass spectrometric characteristics of the compound:

[0297] Using electrospray ionization: calcd for C 34 H 30 N4O8Na + ,([M+Na] + )645.1961, found 645.1967.

[0298] The physicochemical properties of compound V-2 are as follows:

[0299] 1) White solid, melting point 114.3–114.9°C;

[0300] 2) NMR spectrum characteristics of the compound:

[0301] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.92 (d, J = 2.4Hz, 1H, Ar-H), 7.82 (d, J = 2.4Hz, 1H, Ar-H), 7.72 (d, J = 1.6Hz, 1H,Ar-H),7.51–7.54(m,5H,Ar-H),7.20(s,2H,Ar-H),7.18(s,2H,Ar-H),5.03–5.09(m,1H,-CH2-C H -CH2-),4.96–5.02(m,1H,-CH2-C H -CH2-),3.98(s,3H,-OC H 3),3.53(s,3H,-OC H 3),3.41–3.51(m,2H),2.98–3.21(m,6H),2.37(s,6H,2×-C H 3). 13C NMR (100MHz, CDCl3): δ=156.6,156.5,151.7,149.5,144.7,143.8,140.6,140.5,136.6,135.9,134.8,134.1,134 .0,132.1,129.5,126.6,126.5,126.4,126.3,125.5,124.6,80.6,80.1,62.8,62.3,40.2,39.9,35.1,35.0,21.4.

[0302] 3) High-resolution mass spectrometric characteristics of the compound:

[0303] Using electrospray ionization: calcd for C 36 H 34 N4O8Na + ,([M+Na] + )673.2274, found 673.2277.

[0304] The physicochemical properties of compound V-3 are as follows:

[0305] 1) White solid, melting point 129.8–130.5°C;

[0306] 2) NMR spectrum characteristics of the compound:

[0307] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.92 (d, J = 2.4Hz, 1H, Ar-H), 7.82 (d, J = 1.2Hz, 1H, Ar-H), 7.72 (d, J = 1.6Hz, 1H, Ar-H), 7.51 (d, J = 1.6Hz, 1H,Ar-H),7.43(d,J=4.8Hz,2H,Ar-H),7.32–7.35(m,2H,Ar-H),7.15(s,1H,Ar-H),7.13(s,1H,Ar-H),5.02–5.08(m,1H,-CH2-C H -CH2-),4.95–5.01(m,1H,-CH2-C H -CH2-),3.98(s,3H,-OC H 3),3.53(s,3H,-OC H 3),3.40–3.50(m,2H),2.97–3.21(m,6H),2.27(s,12H,4×-C H 3). 13C NMR (100MHz, CDCl3): δ=156.7,156.6,151.7,149.5,144.7,143.8,139.3,139.2,137.1,136.6,135.9,134.8,134.1,134 .0,132.1,130.0,127.7,126.8,126.7,125.5,124.6,124.2,80.5,80.0,62.8,62.3,40.2,40.0,35.1,35.0,19.8,19.7.

[0308] 3) High-resolution mass spectrometric characteristics of the compound:

[0309] Using electrospray ionization: calcd for C 38 H 38 N4O8Na + ,([M+Na] + )701.2587, found 701.2591.

[0310] The physicochemical properties of compound V-4 are as follows:

[0311] 1) Pale yellow solid, melting point 113.8–114.4°C;

[0312] 2) NMR spectrum characteristics of the compound:

[0313] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.94 (d, J = 2.0Hz, 1H, Ar-H), 7.83 (d, J = 2.0Hz, 1H, Ar-H), 7.72 (d, J = 1.6Hz, 1H, Ar-H), 7.5 5–7.58(m,4H,Ar-H),7.52(d,J=1.6Hz,1H,Ar-H),7.26(s,2H,Ar-H),7.24(s,2H,Ar-H),5.04–5.10(m,1H,-CH2-C H -CH2-),4.96–5.02(m,1H,-CH2-C H -CH2-),3.98(s,3H,-OC H 3),3.53(s,3H,-OC H 3),3.42–3.49(m,2H),3.15–3.21(m,2H),3.02–3.12(m,4H),2.87–2.97(m,2H,2×-C H -CH3),1.26(d,J=1.6Hz,6H,2×-CH-CH 3),1.24(d,J=1.6Hz,6H,2×-CH-C H 3). 13 CNMR (100MHz, CDCl3): δ=156.6,156.5,151.7,151.5,151.4,149.5,144.7,143.8,136.6,135.9,134.7,134.1 ,134.0,132.1,126.9,126.8,126.7,125.5,124.6,80.5,80.0,62.8,62.3,40.2,39.9,35.1,35.0,34.1,23.8.

[0314] 3) High-resolution mass spectrometric characteristics of the compound:

[0315] Using electrospray ionization: calcd for C 40 H 42 N4O8Na + ,([M+Na] + )729.2900, found 729.2901.

[0316] The physicochemical properties of compound V-5 are as follows:

[0317] 1) White solid, melting point 124.6–125.1°C;

[0318] 2) NMR spectrum characteristics of the compound:

[0319] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.94 (d, J = 2.0Hz, 1H, Ar-H), 7.83 (d, J = 2.0Hz, 1H, Ar-H), 7.73 (d, J = 2.0Hz, 1H, Ar-H), 7.55–7.59 (m ,4H,Ar-H),7.52(d,J=1.2Hz,1H,Ar-H),7.43(d,J=1.2Hz,2H,Ar-H),7.41(d,J=1.2Hz,2H,Ar-H),5.04–5.10(m,1H,-CH2-C H -CH2-),4.96–5.02(m,1H,-CH2-C H -CH2-),3.98(s,3H,-OC H 3),3.53(d,J=1.6Hz,3H,-OC H3),3.43–3.49(m,2H),2.98–3.21(m,6H),1.32(s,9H,3×-CC H 3),1.31(s,9H,3×-CC H 3). 13 C NMR (100MHz, CDCl3): δ=156.5,156.4,153.8,153.7,151.7,149.5,144.7,143.8,136.6,136.0,134.8,134.1,134.0 ,132.1,126.5,126.4,126.3,125.7,125.5,124.6,80.6,80.1,62.8,62.3,40.2,39.9,39.8,35.1,35.0,34.9,31.1.

[0320] 3) High-resolution mass spectrometric characteristics of the compound:

[0321] Using electrospray ionization: calcd for C 42 H 46 N4O8Na + ,([M+Na] + )757.3213, found 757.3204.

[0322] The physicochemical properties of compound V-6 are as follows:

[0323] 1) White solid, melting point 133.5–134.1°C;

[0324] 2) NMR spectrum characteristics of the compound:

[0325] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.94 (d, J = 2.4Hz, 1H, Ar-H), 7.91–7.92 (m, 1H, Ar-H), 7.90 (d, J = 1.6Hz, 1H, Ar-H), 7.86 (s, 2H, Ar-H), 7.83–7.84 (m,5H,Ar-H),7.81(s,2H,Ar-H),7.75(d,J=2.0Hz,1H,Ar-H),7.53–7.54(m,1H,Ar-H),7.48–7.52(m,4H,Ar-H),5.10–5.16(m,1H,-CH2-C H -CH2-),5.02–5.08(m,1H,-CH2-C H -CH2-),4.00(s,3H,-OC H3),3.56–3.63(m,2H),3.53(s,3H,-OC H 3),3.02–3.30(m,6H). 13 C NMR (100MHz, CDCl3): δ=157.1,157.0,152.0,149.8,145.1,144.1,136.9,136.2,135.1,134.4,134.2,133.3,133.2,132. 5,129.0,128.9,128.7,128.2,127.6,127.3,127.2,127.1,125.8,124.8,123.7,81.2,80.7,63.1,62.6,40.5,40.0,35.4.

[0326] 3) High-resolution mass spectrometric characteristics of the compound:

[0327] Using electrospray ionization: calcd for C 42 H 34 N4O8Na + ,([M+Na] + )745.2274, found 745.2264.

[0328] The physicochemical properties of compound V-7 are as follows:

[0329] 1) White solid, melting point 129.8–130.4°C;

[0330] 2) NMR spectrum characteristics of the compound:

[0331] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.96(d,J=2.0Hz,1H,Ar-H),7.93(s,1H,Ar-H),7.91(s,1H,Ar-H),7.89(s,2H,Ar-H),7.85(d,J=2.0Hz,1 H,Ar-H),7.75(d,J=2.0Hz,1H,Ar-H),7.70(s,1H,Ar-H),7.68(s,1H,Ar-H),7.52–7.56(m,3H,Ar-H),5.07–5.19(m,2H,2×-CH2-C H -CH2-),3.99(s,3H,-OCH3),3.58(s,3H,-OCH3),3.52–3.56(m,1H),3.46–3.50(m,1H),3.05–3.23(m,6H). 13C NMR (100MHz, CDCl3): δ=155.4,155.3,152.0,149.9,145.1,144.0,136.9,136.2,135.0,134.1,133.9,133.7,133.6,132. 3,131.0,130.9,130.8,130.4,130.3,130.1,125.8,125.0,118.4,113.4,81.8,81.3,63.1,62.7,40.4,39.6,35.4,32.1.

[0332] 3) High-resolution mass spectrometric characteristics of the compound:

[0333] Using electrospray ionization: calcd for C 36 H 28 N6O8Na + ,([M+Na] + )695.1866, found 695.1870.

[0334] The physicochemical properties of compound V-8 are as follows:

[0335] 1) White solid, melting point 134.5–134.9°C;

[0336] 2) NMR spectrum characteristics of the compound:

[0337] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.95 (d, J=2.0Hz, 1H, Ar-H), 7.82 (d, J=2.4Hz, 1H, Ar-H), 7.73 (d, J=2.0Hz, 1H, Ar-H), 7.70 (d, J=1.2 Hz,2H,Ar-H),7.51(d,J=2.0Hz,1H,Ar-H),7.49(d,J=1.6Hz,1H,Ar-H),7.46–7.48(m,3H,Ar-H),5.02–5.14(m,2H,2×-CH2-C H -CH2-),3.98(s,3H,-OC H 3),3.57(s,3H,-OC H 3),3.40–3.50(m,2H),3.01–3.21(m,6H). 13C NMR (100MHz, CDCl3): δ=154.9,154.8,151.7,149.6,144.8,143.8,136.6,135.7,134.7,134.4,134.3,133.8,133. 6,133.1,132.1,130.8,129.3,129.2,128.4,128.3,125.7,125.5,124.7,81.3,80.8,62.8,62.4,40.1,39.4,35.1.

[0338] 3) High-resolution mass spectrometric characteristics of the compound:

[0339] Using electrospray ionization: calcd for C 34 H 26 N4O8Na 35 Cl4 + ,([M+Na] + )781.0402,found781.0403.

[0340] The physicochemical properties of compound VI-1 are as follows:

[0341] 1) Pale yellow solid, melting point 112.1–112.8°C;

[0342] 2) NMR spectrum characteristics of the compound:

[0343] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.80(s,2H,Ar-H),7.62–7.64(m,4H,Ar-H),7.54(s,2H,Ar-H),7.40(d,J=4.4Hz,6H,Ar-H),4.98–5.05(m,2H,2×-CH2-C H -CH2-),3.55(s,6H,2×-OCH3),3.46–3.53(m,2H),3.05–3.12(m,6H). 13 C NMR (100MHz, CDCl3): δ=156.8,150.2,144.4,137.2,133.7,132.8,130.6,129.5,129.1,126.9,126.4,81.0,62.6,40.3,39.9.

[0344] 3) High-resolution mass spectrometric characteristics of the compound:

[0345] Using electrospray ionization: calcd for C 34 H30 N4O8Na + ,([M+Na] + )645.1961, found 645.1967.

[0346] The physicochemical properties of compound VI-2 are as follows:

[0347] 1) Pale yellow solid, melting point 124.8–125.7°C;

[0348] 2) NMR spectrum characteristics of the compound:

[0349] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.80(s,2H,Ar-H),7.50–7.58(m,6H,Ar-H),7.21(s,2H,Ar-H),7.19(s,2H,Ar-H),4.95–5.03(m,2H,2×-CH2-C H -CH2-),3.55(s,3H,-OC H 3),3.54(s,3H,-OC H 3),3.50(dd,J=10.4,16.4Hz,2H),2.99–3.09(m,6H),2.37(s,6H,2×-C H 3). 13 C NMR (100MHz, CDCl3): δ=156.4,149.9,144.1,140.6,136.9,133.5,133.4,132.6,129.5,126.6,126.4,126.1,80.5,62.3,40.1,39.8,21.4.

[0350] 3) High-resolution mass spectrometric characteristics of the compound:

[0351] Using electrospray ionization: calcd for C 36 H 34 N4O8Na + ,([M+Na] + )673.2274, found 673.2275.

[0352] The physicochemical properties of compound VI-3 are as follows:

[0353] 1) White solid, melting point 114.3–115.0°C;

[0354] 2) NMR spectrum characteristics of the compound:

[0355] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.79(s,2H,Ar-H),7.53(s,2H,Ar-H),7.42(s,2H,Ar-H),7.34(s,1H ,Ar-H),7.32(s,1H,Ar-H),7.15(s,1H,Ar-H),7.13(s,1H,Ar-H),4.95–5.02(m,2H,2×-CH2-C H -CH2-),3.55(s,3H,-OC H 3),3.54(s,3H,-OC H 3),3.49(dd,J=10.4,16.4Hz,2H),2.98–3.09(m,6H),2.27(s,12H,4×-C H 3). 13 CNMR (100MHz, CDCl3): δ=156.6,149.9,144.1,139.3,137.1,136.9,133.5,133.4,1 32.6,130.0,127.7,126.7,126.1,124.2,80.4,62.3,40.1,39.8,39.7,19.8,19.7.

[0356] 3) High-resolution mass spectrometric characteristics of the compound:

[0357] Using electrospray ionization: calcd for C 38 H 38 N4O8Na + ,([M+Na] + )701.2587, found 701.2589.

[0358] The physicochemical properties of compound VI-4 are as follows:

[0359] 1) Pale yellow solid, melting point 118.0–118.9°C;

[0360] 2) NMR spectrum characteristics of the compound:

[0361] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ = 7.80 (d, J = 1.6Hz, 2H, Ar-H), 7.56 (s, 2H, Ar-H), 7.54 ( s,4H,Ar-H),7.26(s,2H,Ar-H),7.24(s,2H,Ar-H),4.96–5.03(m,2H,2×-CH2-C H -CH2-),3.54(s,6H,2×-OC H 3),3.51(dd,J=10.4,16.4Hz,2H),3.04–3.10(m,6H),2.89–2.96(m,2H,2×-C H -CH3),1.26(d,J=6.8Hz,12H,4×-CH-C H 3). 13 C NMR (100MHz, CDCl3): δ=156.4,151.5,149.9,144.1,136.9,133.4,132.6,126.9,126.7,126.1,80.5,62.3,40.0,39.8,34.1,23.8.

[0362] 3) High-resolution mass spectrometric characteristics of the compound:

[0363] Using electrospray ionization: calcd for C 40 H 42 N4O8Na + ,([M+Na] + )729.2900, found 729.2894.

[0364] The physicochemical properties of compound VI-5 are as follows:

[0365] 1) Pale yellow solid, melting point 118.2–118.8°C;

[0366] 2) NMR spectrum characteristics of the compound:

[0367] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 7.80 (d, J = 1.6Hz, 2H, Ar-H), 7.57 (s, 2H, Ar-H), 7.54–7.5 5(m,4H,Ar-H),7.43(s,2H,Ar-H),7.40(s,2H,Ar-H),4.96–5.03(m,2H,2×-CH2-C H-CH2-),3.55(s,3H,-OCH3),3.54(s,3H,-OCH3),3.48–3.51(m,1H),3.44–3.47(m,1H),3.03–3.10(m,6H),1.32(s,18H,6×-C-CH3). 13 C NMR (100MHz, CDCl3): δ=156.4,153.8,149.9,144.1,136.9,133.4,132.6,126.5,126.3,126.1,125.7,80.5,62.3,40.0,39.7,34.9,31.1.

[0368] 3) High-resolution mass spectrometric characteristics of the compound:

[0369] Using electrospray ionization: calcd for C 42 H 46 N4O8Na + ,([M+Na] + )757.3213, found 757.3209.

[0370] The physicochemical properties of compound VI-6 are as follows:

[0371] 1) Pale yellow solid, melting point 130.0–130.6°C;

[0372] 2) NMR spectrum characteristics of the compound:

[0373] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.92(s,1H,Ar-H),7.90(s,1H,Ar-H),7.82–7.86(m,10H,Ar-H),7.49–7.54(m,6H,Ar-H),5.01–5.09(m,2H,2×-CH2-C H -CH2-),3.57–3.62(m,2H),3.54(s,6H,2×-OCH3),3.16–3.22(m,2H),3.02–3.10(m,4H). 13 C NMR (100MHz, CDCl3): δ=156.6,150.0,144.1,136.9,134.0,133.3,132.9,132.6,128.6, 128.4,128.2,127.9,127.3,126.9,126.8,126.7,126.1,123.3,80.8,62.3,40.1,39.6.

[0374] 3) High-resolution mass spectrometric characteristics of the compound:

[0375] Using electrospray ionization: calcd for C 42 H 34 N4O8Na + ,([M+Na] + )745.2274, found 745.2266.

[0376] The physicochemical properties of compound VI-7 are as follows:

[0377] 1) White solid, melting point 130.2–130.9°C;

[0378] 2) NMR spectrum characteristics of the compound:

[0379] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.93(s,1H,Ar-H),7.91(s,1H,Ar-H),7.89(s,2H,Ar-H),7.82(d,J=1.6Hz,2H,Ar-H),7 .71(s,1H,Ar-H),7.69(s,1H,Ar-H),7.57(s,3H,Ar-H),7.55(d,J=8.0Hz,1H,Ar-H),5.05–5.13(m,2H,2×-CH2-C H -CH2-),3.60(s,6H,2×-OCH3),3.52–3.55(m,1H),3.48–3.51(m,1H),3.07–3.14(m,6H). 13 C NMR (100MHz, CDCl3): δ=155.2,150.3,144.5,137.2,133.7,133.4,132.8, 130.9,130.8,130.3,130.1,126.4,118.3,113.5,81.8,62.6,40.3,39.5.

[0380] 3) High-resolution mass spectrometric characteristics of the compound:

[0381] Using electrospray ionization: calcd for C 36 H 28 N6O8Na + ,([M+Na] + )695.1866, found 695.1873.

[0382] The physicochemical properties of compound VI-8 are as follows:

[0383] 1) Pale yellow solid, melting point 120.2–120.7°C;

[0384] 2) NMR spectrum characteristics of the compound:

[0385] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=7.80(d,J=2.4Hz,2H,Ar-H),7.69(s,2H,Ar-H),7.53(d,J=2.4Hz,2H,Ar-H),7.48(s,4H,Ar-H),5.01–5.08(m,2H,2×-CH2-C H -CH2-),3.59(s,6H,2×-OC H 3), 3.49 (dd, J=10.4, 16.4Hz, 2H, Ar-H), 3.01–3.07 (m, 6H). 13 C NMR (100MHz, CDCl3): δ=154.8,150.0,144.2,136.8,134.4,133.2,133.1,132.5,130.9,129.2,128.4,126.1,125.6,81.3,62.3,40.0,39.4.

[0386] 3) High-resolution mass spectrometric characteristics of the compound:

[0387] Using electrospray ionization: calcd for C 34 H 26 N4O8Na 35 Cl4 + ,([M+Na] + )781.0402,found781.0401.

[0388] The physicochemical properties of compound VII-1 are as follows:

[0389] 1) Yellow solid, melting point 125.4–125.9°C;

[0390] 2) NMR spectrum characteristics of the compound:

[0391] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 HNMR (400MHz, CDCl3): δ = 11.10 (s, 1H, -O H ),11.07(s,1H,-O H),8.25(s,1H,Ar-H),8.08(s,1H,Ar-H),7.83(s,1H,Ar-H), 7.63–7.67(m,5H,Ar-H),7.41(s,6H,Ar-H),5.11–5.19(m,1H,-CH2-CH-CH2-),4.98–5.06(m, 1H, -CH2-C H -CH2-),3.53(dd,J=10.0,16.4Hz,2H),3.14–3.23(m,3H),3.00–3.11(m,3H). 13 C NMR (100MHz, CDCl3): δ=157.0,156.9,153.4,151.8,140.6,139.7,134.2,133.8,130.6,130.5,130.4,12 9.8,129.7,129.5,129.1,129.0,128.7,127.8,127.0,125.5,124.7,81.2,79.9,40.3,40.2,40.0,35.6.

[0392] 3) High-resolution mass spectrometric characteristics of the compound:

[0393] Using electrospray ionization: calcd for C 32 H 26 N4O8Na + ,([M+Na] + )617.1648, found 617.1650.

[0394] The physicochemical properties of compound VII-2 are as follows:

[0395] 1) Pale yellow solid, melting point 128.5–129.1°C;

[0396] 2) NMR spectrum characteristics of the compound:

[0397] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 HNMR (400MHz, CDCl3): δ=11.08(s,1H,-OH),11.06(s,1H,-OH),8.24(s,1H,Ar-H),8.08(s,1H,Ar-H),7.83(s,1H,Ar-H),7.62(s,1H,Ar-H), 7.56(s,1H,Ar-H),7.54(s,2H,Ar-H),7.52(s,1H,Ar-H),7.21(d,J=2.4Hz,2H,Ar-H),7.19(d,J=2.0Hz,2H,Ar-H),5.09–5.16(m,1H,-CH2-C H -CH2-),4.95–5.03(m,1H,-CH2-CH -CH2-),3.50(dd,J=10.4,16.4Hz,2H),3.16–3.20(m,2H),3.02–3.14(m,4H),2.37(s,3H,-CH3),2.36(s,3H,-CH3). 13 C NMR (100MHz, CDCl3): δ=156.6,156.5,153.1,151.5,140.6,140.5,140.3,139.4,133.9,133.5,130. 2,129.5,129.4,128.4,127.5,126.6,126.4,125.1,124.4,80.7,79.4,40.0,39.9,39.8,35.2,21.4.

[0398] 3) High-resolution mass spectrometric characteristics of the compound:

[0399] Using electrospray ionization: calcd for C 34 H 30 N4O8Na + ,([M+Na] + )645.1961, found 645.1968.

[0400] The physicochemical properties of compound VII-3 are as follows:

[0401] 1) Yellow solid, melting point 135.5–136.3°C;

[0402] 2) NMR spectrum characteristics of the compound:

[0403] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 HNMR (400MHz, CDCl3): δ=11.08(s,1H,-OH),11.06(s,1H,-OH),8.24(s,1H,Ar-H),8.07(s,1H,Ar-H),7.83(s,1H,Ar-H),7.62(s,1H,Ar-H),7. 46(s,1H,Ar-H),7.43(s,1H,Ar-H),7.33–7.37(m,2H,Ar-H),7.16(d,J=2.8Hz,1H,Ar-H),7.14(d,J=2.8Hz,1H,Ar-H),5.08–5.15(m,1H,-CH2-C H -CH2-),4.94–5.02(m,1H,-CH2-C H-CH2-),3.49(dd,J=10.4,16.8Hz,2H),3.16–3.21(m,2H),2.97–3.13(m,4H),2.27(s,12H,4×-CH3). 13 C NMR (100MHz, CDCl3): δ=156.7,156.6,153.1,151.5,140.3,139.4,139.3,139.2,137.1,137.0,133.9,133.5,130.1,130. 0,129.5,128.4,127.7,127.5,126.9,126.7,125.1,124.4,124.3,124.2,80.6,79.3,40.0,39.9,35.2,19.8,19.7,19.6.

[0404] 3) High-resolution mass spectrometric characteristics of the compound:

[0405] Using electrospray ionization: calcd for C 36 H 34 N4O8Na + ,([M+Na] + )673.2274, found 673.2277.

[0406] The physicochemical properties of compound VII-4 are as follows:

[0407] 1) Yellow solid, melting point 140.6–141.3°C;

[0408] 2) NMR spectrum characteristics of the compound:

[0409] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 HNMR (400MHz, CDCl3): δ=11.08(s,1H,-OH),11.06(s,1H,-OH),8.24–8.25(m,1H,Ar-H),8.08(d,J=1.6Hz,1H,Ar-H),7.83(s,1H,Ar -H),7.62(s,1H,Ar-H),7.60(s,1H,Ar-H),7.58(s,2H,Ar-H),7.56(s,1H,Ar-H),7.24–7.27(m,4H,Ar-H),5.08–5.16(m,1H,-CH2-C H -CH2-),4.95–5.03(m,1H,-CH2-C H-CH2-),3.50(dd,J=10.4,16.8Hz,2H),3.13–3.20(m,3H),3.02–3.09(m,3H),2.89–2.96(m,2H,2×-C H -CH3),1.26(d,J=1.6Hz,6H,2×-CH-C H 3),1.24(d,J=1.6Hz,6H,2×-CH-C H 3). 13 C NMR (100MHz, CDCl3): δ=156.6,156.5,153.1,151.5,151.4,140.3,139.4,133.9,133.5,130.2,129.5,1 28.4,127.5,127.0,126.9,126.8,126.7,125.1,124.4,80.7,79.4,40.0,39.9,39.8,35.2,34.1,23.8.

[0410] 3) High-resolution mass spectrometric characteristics of the compound:

[0411] Using electrospray ionization: calcd for C 38 H 38 N4O8Na + ,([M+Na] + )701.2587, found 701.2588.

[0412] The physicochemical properties of compound VII-5 are as follows:

[0413] 1) Yellow solid, melting point 145.6–146.0°C;

[0414] 2) NMR spectrum characteristics of the compound:

[0415] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1HNMR (400MHz, CDCl3): δ = 11.08 (s, 1H, -OH), 11.06 (s, 1H, -OH), 8.24–8.25 (m ,1H,Ar-H),8.08(d,J=1.6Hz,1H,Ar-H),7.83–7.84(m,1H,Ar-H),7.62–7.63 (m,1H,Ar-H),7.61(s,1H,Ar-H),7.59(s,1H,Ar-H),7.57(s,1H,Ar-H),7.43 (d,J=2.4Hz,2H,Ar-H),7.41(d,J=2.4Hz,2H,Ar-H),5.08–5.16(m,1H,-CH2-C H -CH2-),4.96–5.03(m,1H,-CH2-C H -CH2-),3.44–3.51(m,2H),3.08–3.21(m,3H),2.98–3.06(m,3H),1.32(s,9H,3×-C-CH3),1.31(s,9H,3×-C-CH3). 13 C NMR (100MHz, CDCl3): δ=156.5,156.4,153.7,153.6,153.1,151.5,140.3,139.4,133.9,133.5,130.2,129.5,1 28.4,127.5,126.6,126.5,126.4,125.8,125.7,125.2,124.4,80.7,79.4,40.0,39.9,35.2,34.9,31.2,26.9.

[0416] 3) High-resolution mass spectrometric characteristics of the compound:

[0417] Using electrospray ionization: calcd for C 40 H 42 N4O8Na + ,([M+Na] + )729.2900, found 729.2897.

[0418] The physicochemical properties of compound VII-6 are as follows:

[0419] 1) Yellow solid, melting point 144.3–145.1°C;

[0420] 2) NMR spectrum characteristics of the compound:

[0421] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1HNMR (400MHz, CDCl3): δ = 11.10 (s, 1H, -OH), 11.07 (s, 1H, -OH), 8.26 (d, J = 2.4Hz, 1H, Ar-H), 8.10 (d, J = 2.0Hz, 1H, Ar-H), 7.92–7.96 (m ,2H,Ar-H),7.89(s,1H,Ar-H),7.81–7.85(m,8H,Ar-H),7.65(d,J=2.0Hz,1H,Ar-H),7.49–7.51(m,4H,Ar-H),5.15–5.23(m,1H,-CH2-C H -CH2-),5.03–5.10(m,1H,-CH2-C H -CH2-),3.63(dd,J=10.4,16.4Hz,2H),3.13–3.31(m,4H),3.03–3.11(m,2H). 13 C NMR (100MHz, CDCl3): δ=156.8,156.7,153.1,151.5,140.3,139.4,134.1,133.9,133.5,133.0,132.9,130.2,129.4,128.7,128 .6,128.4,127.9,127.3,127.2,127.0,126.8,125.2,124.4,123.5,123.4,81.0,79.8,40.0,39.8,39.6,35.2,31.6,26.9,22.7.

[0422] 3) High-resolution mass spectrometric characteristics of the compound:

[0423] Using electrospray ionization: calcd for C 40 H 30 N4O8Na + ,([M+Na] + )717.1961, found 717.1959.

[0424] The physicochemical properties of compound VII-7 are as follows:

[0425] 1) Yellow solid, melting point 150.4–151.1°C;

[0426] 2) NMR spectrum characteristics of the compound:

[0427] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1HNMR (400MHz, CDCl3): δ = 11.11 (s, 1H, -OH), 11.09 (s, 1H, -OH), 8.26–8.27 (m, 1H, Ar-H),8.09(d,J=2.0Hz,1H,Ar-H),7.91–7.94(m,3H,Ar-H),7.87(d,J=1.6Hz,1H ,Ar-H),7.85(d,J=2.4Hz,1H,Ar-H),7.69–7.70(m,1H,Ar-H),7.67–7.68(m,1H,A r-H),7.63–7.64(m,1H,Ar-H),7.52–7.56(m,2H,Ar-H),5.18–5.26(m,1H,-CH2-C H -CH2-),5.06–5.13(m,1H,-CH2-C H -CH2-),3.53(dd,J=10.4,16.8Hz,2H),3.06–3.27(m,6H). 13 C NMR (100MHz, CDCl3): δ=155.0,154.9,153.1,151.6,140.2,139.2,133.9,133.6,133.4,133.3,130.9,130.7,130.6,130.2,1 30.1,129.8,129.7,129.0,128.0,127.5,125.2,124.5,118.1,118.0,113.3,113.2,81.6,80.4,39.9,39.4,39.2,35.2,29.7.

[0428] 3) High-resolution mass spectrometric characteristics of the compound:

[0429] Using electrospray ionization: calcd for C 34 H 24 N6O8Na + ,([M+Na] + )667.1553, found 667.1553.

[0430] The physicochemical properties of compound VII-8 are as follows:

[0431] 1) Yellow solid, melting point 156.3–157.1°C;

[0432] 2) NMR spectrum characteristics of the compound:

[0433] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1HNMR (400MHz, CDCl3): δ = 11.10 (s, 1H, -O H ),11.09(s,1H,-O H ),8.26(s,1H,Ar-H),8.08(s,1H,Ar-H),7.83(s,1H,Ar-H),7.72(s,1H,Ar-H),7.69 (s,1H,Ar-H),7.62(s,1H,Ar-H),7.46–7.51(m,4H,Ar-H),5.14–5.21(m,1H,-CH2-C H -CH2-),5.02–5.09(m,1H,-CH2-C H -CH2-),3.42–3.48(m,2H),3.01–3.24(m,6H). 13 CNMR (100MHz, CDCl3): δ=155.0,154.8,153.1,151.6,140.2,139.3,134.4,134.3,133.9,133.5,133.2 ,130.9,130.2,129.4,129.1,128.4,128.1,127.5,125.7,125.2,124.5,81.4,80.2,39.9,39.5,39.3.

[0434] 3) High-resolution mass spectrometric characteristics of the compound:

[0435] Using electrospray ionization: calcd for C 32 H 22 N4O8Na 35 Cl4 + ,([M+Na] + )753.0089,found753.0082.

[0436] The physicochemical properties of compound VIII-1 are as follows:

[0437] 1) Yellow solid, melting point 136.0–136.5°C;

[0438] 2) NMR spectrum characteristics of the compound:

[0439] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 10.86 (s, 2H, 2×-O H),8.11(s,2H,Ar-H),7.63–7.65(m,4H,Ar-H),7.60(s,2H,Ar-H),7.40(d,J=4.8Hz,6H,Ar-H),4.97–5.05(m,2H,2×-CH2-C H -CH2-),3.51(dd,J=10.4,16.8Hz,2H),2.98–3.12(m,6H). 13 C NMR (100MHz, CDCl3): δ=156.9,152.2,140.9,134.0,130.6,129.6,129.2,129.1,127.5,126.9,125.9,81.2,60.7,40.2,39.9.

[0440] 3) High-resolution mass spectrometric characteristics of the compound:

[0441] Using electrospray ionization: calcd for C 32 H 26 N4O8Na + ,([M+Na] + )617.1648, found 617.1646.

[0442] The physicochemical properties of compound VIII-2 are as follows:

[0443] 1) Orange-yellow solid, melting point 140.6–141.0°C;

[0444] 2) NMR spectrum characteristics of the compound:

[0445] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 10.85 (s, 2H, 2×-O H ),8.11(s,2H,Ar-H)7.59(s,2H,Ar-H),7.54(s,2H,Ar-H),7.52(s,2H,Ar-H),7.21(s,2H,Ar-H),7.19(s,2H,Ar-H),4.95–5.02(m,2H,2×-CH2-C H -CH2-),3.49(dd,J=10.0,16.4Hz,2H),2.97–3.10(m,6H),2.37(s,6H,2×-C H 3). 13C NMR (100MHz, CDCl3): δ=156.5,151.9,140.6,140.5,133.7,129.5,128.9,127.2,126.6,126.5,125.5,80.7,39.9,39.8,26.9,21.5.

[0446] 3) High-resolution mass spectrometric characteristics of the compound:

[0447] Using electrospray ionization: calcd for C 34 H 30 N4O8Na + ,([M+Na] + )645.1961, found 645.1965.

[0448] The physicochemical properties of compound VIII-3 are as follows:

[0449] 1) Yellow solid, melting point 145.7–146.4°C;

[0450] 2) NMR spectrum characteristics of the compound:

[0451] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ=10.85(s,2H,2×-OH),8.11(s,2H,Ar-H)7.60(s,2H,Ar-H),7.44(s,2H,Ar-H),7 .35(s,1H,Ar-H),7.35(s,1H,Ar-H),7.16(s,1H,Ar-H),7.14(s,1H,Ar-H),4.94–5.02(m,2H,2×-CH2-C H -CH2-),3.48(dd,J=10.0,16.4Hz,2H),3.04–3.09(m,4H),2.96–3.01(m,2H),2.28(s,12H,4×-CH3). 13 CNMR (100MHz, CDCl3): δ=156.6,151.9,140.6,139.3,137.1,133.7,130.0 ,129.0,127.7,127.2,126.8,125.5,124.2,80.6,39.9,39.8,19.8,19.7.

[0452] 3) High-resolution mass spectrometric characteristics of the compound:

[0453] Using electrospray ionization: calcd for C 36 H34 N4O8Na + ,([M+Na] + )673.2274, found 673.2275.

[0454] The physicochemical properties of compound VIII-4 are as follows:

[0455] 1) Pale yellow solid, melting point 126.4–126.9°C;

[0456] 2) NMR spectrum characteristics of the compound:

[0457] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 10.86 (s, 2H, 2×-OH), 8.11 (d, J = 1.6Hz, 2H, Ar-H) 7.61 (d, J = 2.0Hz, 2H, Ar-H), 7 .58(s,2H,Ar-H),7.56(s,2H,Ar-H),7.27(s,2H,Ar-H),7.25(s,2H,Ar-H),4.95–5.03(m,2H,2×-CH2-C H -CH2-),3.50(dd,J=10.4,16.4Hz,2H),3.05–3.10(m,4H),2.96–3.01(m,2H),2.89–2.94(m,2H,2×-C H -CH3),1.26(d,J=6.8Hz,12H,4×-CH-C H 3). 13 C NMR (100MHz, CDCl3): δ=156.5,151.9,151.5,140.6,133.7,128.9,127.2,126.9,126.8,126.7,125.5,80.7,39.9,39.8,34.1,23.8.

[0458] 3) High-resolution mass spectrometric characteristics of the compound:

[0459] Using electrospray ionization: calcd for C 38 H 38 N4O8Na + ,([M+Na] + )701.2587, found 701.2586.

[0460] The physicochemical properties of compound VIII-5 are as follows:

[0461] 1) Yellow solid, melting point 141.0–141.5°C;

[0462] 2) NMR spectrum characteristics of the compound:

[0463] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 10.86 (s, 2H, 2×-OH), 8.11 (d, J = 2.0Hz, 2H, Ar-H), 7.61 (d, J = 2.0Hz, 2H, Ar-H), 7.59(s,2H,Ar-H),7.57(s,2H,Ar-H),7.43(s,2H,Ar-H),7.41(s,2H,Ar-H),4.96–5.03(m,2H,2×-CH2-C H -CH2-),3.50(dd,J=10.0,16.4Hz,2H),3.05–3.11(m,4H),2.96–3.01(m,2H),1.32(s,18H,6×-C-CH3). 13 C NMR (100MHz, CDCl3): δ=156.4,153.7,151.9,140.7,133.7,128.9,127.2,126.5,126.4,125.7,125.5,80.7,39.9,39.8,34.9,31.1.

[0464] 3) High-resolution mass spectrometric characteristics of the compound:

[0465] Using electrospray ionization: calcd for C 40 H 42 N4O8Na + ,([M+Na] + )729.2900, found 729.2895.

[0466] The physicochemical properties of compound VIII-6 are as follows:

[0467] 1) Yellow solid, melting point 152.4–152.9°C;

[0468] 2) NMR spectrum characteristics of the compound:

[0469] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ = 10.85 (s, 2H, 2×-OH), 8.12–8.14 (m, 2H, Ar-H), 7.94 (d, J = 1.2Hz, 1H, Ar-H), 7.92 (d, J = 1.6Hz, 1H,Ar-H),7.81–7.86(m,8H,Ar-H),7.60(d,J=2.4Hz,2H,Ar-H),7.48–7.53(m,4H,Ar-H),5.01–5.09(m,2H,2×-CH2-C H -CH2-),3.61(dd,J=10.4,16.4Hz,2H),3.16–3.22(m,2H),2.99–3.11(m,4H). 13 C NMR (100MHz, CDCl3): δ=157.0,152.2,140.9,134.4,134.0,133.2,129.1,128.9,12 8.7,128.2,127.6,127.3,127.2,127.1,125.9,123.7,81.3,40.2,39.9,30.0,29.6.

[0470] 3) High-resolution mass spectrometric characteristics of the compound:

[0471] Using electrospray ionization: calcd for C 40 H 31 N4O8 + ,([M+Na] + )695.2142, found 695.2134.

[0472] The physicochemical properties of compound VIII-7 are as follows:

[0473] 1) Yellow solid, melting point 140.1–140.8°C;

[0474] 2) NMR spectrum characteristics of the compound:

[0475] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1H NMR (400MHz, CDCl3): δ=10.89(s,2H,2×-OH),8.13(d,J=2.0Hz,2H,Ar-H),7.92(s,1H,Ar-H),7.90(s,1H,Ar-H),7.88(d,J=1.6H z,2H,Ar-H),7.70(s,1H,Ar-H),7.69(s,1H,Ar-H),7.60–7.62(m,2H,Ar-H),7.52–7.56(m,2H,Ar-H),5.06–5.13(m,2H,2×-CH2-C H -CH2-),3.50–3.53(m,1H),3.46–3.49(m,1H),3.02–3.12(m,6H). 13 C NMR (100MHz, CDCl3): δ=155.2,152.3,140.9,134.1,133.7,131.1,130.9, 130.4,130.1,128.8,127.6,126.0,118.4,113.6,82.0,40.2,39.4,30.0.

[0476] 3) High-resolution mass spectrometric characteristics of the compound:

[0477] Using electrospray ionization: calcd for C 34 H 24 N6O8Na + ,([M+Na] + )667.1553, found 667.1556.

[0478] The physicochemical properties of compound VIII-8 are as follows:

[0479] 1) Yellow solid, melting point 144.9–145.7°C;

[0480] 2) NMR spectrum characteristics of the compound:

[0481] Deuterated chloroform was used as solvent and TMS was used as internal standard. The peaks were assigned as follows: 1 H NMR (400MHz, CDCl3): δ = 10.88 (s, 2H, 2×-O H ),8.11(d,J=1.6Hz,2H,Ar-H),7.69(s,2H,Ar-H),7.59(s,2H,Ar-H),7.48(s,4H,Ar-H),5.02–5.09(m,2H,2×-CH2-C H-CH2-),3.48(dd,J=10.4,16.4Hz,2H),3.01–3.10(m,6H). 13 C NMR (100MHz, CDCl3): δ=154.8,152.0,140.5,134.4,133.8,133.2,130.8,129.3,128.5,128.4,127.2,125.7,125.6,81.4,39.8,39.2.

[0482] 3) High-resolution mass spectrometric characteristics of the compound:

[0483] Using electrospray ionization: calcd for C 32 H 23 N4O8 35 Cl4 + ,([M+Na] + )731.0270,found731.0274.

[0484] Example 77 Biological Activity Assay of the Isoxazoline Hybridized Neolignans Prepared in Examples 1-76

[0485] 1. Test insects: larvae of diamondback moth (Plutellaxylostella) and oriental armyworm (Mythimna separata).

[0486] 2. Test samples and reagents:

[0487] The samples are: isoxazoline hybridized neolignan compounds Ⅰ-1–11, Ⅱ-1–11, Ⅲ-1–11, Ⅳ-1–11, Ⅴ-1–8, Ⅵ-1–8, Ⅶ-1–8 and Ⅷ-1–8 prepared in the examples and positive control agents rotenone and tolfenpyrad; the solvent is acetone.

[0488] 3. Bioassay method:

[0489] (1) Determination of stomach toxicity activity of Plutella xylostella

[0490] The small leaf disc addition method was used to test the stomach poison effect of all samples on diamondback moth. A layer of filter paper with water added to keep moisture was laid on the bottom of the culture dish. 15 strong and lively second-instar diamondback moth larvae with consistent growth and development were picked from each dish and starved for 8 hours. The test samples were weighed and dissolved in acetone to prepare a solution with a concentration of 10 μg / ml. Use a hole puncher to punch fresh cabbage leaves into small leaf discs with a diameter of 1 cm, immerse them in the sample solution to be tested for 3-5 seconds, and feed the test insects after the solvent evaporates naturally. Each compound was repeated 3 times. Each replicate group was fed with a certain number of treated leaves, and continuous observation was performed during the period. When the leaves were eaten, the corresponding poisonous small leaf discs were added. After feeding for 48 hours, fresh and normal cabbage leaves were fed until the end of eclosion. The treatment evenly dipped in an equal amount of acetone solution was used as the blank control group, and rotenone and tolfenpyrad were used as positive control agents. During the entire test period, the temperature was controlled at 25 ± 1 degrees Celsius, the humidity was maintained between 60-80%, and the light / dark time was 12 hours / 12 hours. The number of live test insects and the symptoms of poisoning were regularly observed and recorded, and the mortality rate (Formula-1) and the corrected mortality rate (Formula-2) of the test insects at different periods were calculated according to the following formula. The test results of insecticidal organisms are shown in Table-2.

[0491]

[0492] Table-2 Stomach toxicity of isoxazoline-hybridized neolignans to Plutella xylostella larvae

[0493]

[0494]

[0495] (2) Determination of stomach poison activity of Oriental armyworm

[0496] The same small leaf dish addition method was used. A layer of filter paper with water added to keep moisture was laid at the bottom of the culture dish. Three replicates were set for each compound. Ten early third-instar oriental armyworm larvae were selected for each replicate and starved for 12 hours. All test compounds were prepared into acetone solutions with a concentration of 1 mg / ml for standby use. Fresh corn leaves were cut into small leaves of 1×1 cm after removing the main veins. They were immersed in the test solution for 3-5 seconds. After natural evaporation, the test insects were fed with acetone as a blank control, and rotenone and tolfenpyrad were positive control agents. After the test insects have eaten the leaves, the corresponding poisonous leaves are added. After 48 hours of feeding, normal leaves are fed until they emerge. During the entire test period, the feeding temperature was maintained at 25±1 degrees Celsius, the humidity was 60-80%, and the light / dark time was 12 hours / 12 hours. The number of deaths of test insects, symptoms of poisoning, etc. were observed and recorded regularly, and the mortality rate (Formula-1) and corrected mortality rate (Formula-2) of test insects at different periods were calculated. The results of biological tests are shown in Table-3.

[0497] Table-3 Stomach poison activity of isoxazoline-hybridized neolignans against oriental armyworm

[0498]

[0499]

[0500] 4. Conclusion

[0501] The results of insecticidal bioassay (Table 2) show that the isoxazoline hybridized neolignan compounds (isoxazoline magnolol, isoxazoline and magnolol, isoxazoline nitrated magnolol, isoxazoline nitrated and magnolol derivatives) prepared by the present invention exhibit obvious stomach toxicity to the larvae of diamondback moth; especially the derivatives III-3, IV-4, IV-6 and VII-4 have a corrected mortality rate of up to 100% for diamondback moth at 72 hours, even exceeding the two commercial insecticides rotenone and tolfenpyrad. At the same time, the 72-hour corrected mortality rates of derivatives I-4, II-3, II-4, II-6, II-11, III-2, III-4, III-5, III-6, III-7, IV-1, IV-3, IV-5, V-6 and VIII-8 also exceed the commercial botanical insecticide rotenone.

[0502] The results of insecticidal bioassay (Table 3) show that the isoxazoline hybridized new lignan compounds (isoxazoline magnolol, isoxazoline and magnolol, isoxazoline nitrated magnolol, isoxazoline nitrated magnolol derivatives) prepared by the present invention treat the larvae of the oriental armyworm, and the mortality rate of the derivative I-9 to the test insects is as high as 100%, and its insecticidal activity far exceeds the botanical insecticide rotenone, and is similar to the insecticidal efficacy of the chemical insecticide tolfenpyrad, which shows that the compound has great potential for further development into a new insecticide. The final corrected mortality of the derivatives I-5, I-11, II-5, II-7, II-8, II-9, III-1, III-2, III-10, III-11, IV-1, IV-2, IV-9, IV-10, IV-11, VII-1, VII-3, VII-4 and VIII-7 to the test armyworm is also better than rotenone, showing a certain application value.

[0503] In summary, the isoxazoline hybridized new lignan compounds (isoxazoline magnolol, isoxazoline and magnolol, isoxazoline nitrated magnolol, isoxazoline nitrated and magnolol derivatives) in the present invention can be used to prepare highly effective new insecticides and applied to the control of diamondback moth and oriental armyworm.

[0504] The specification and drawings of the present invention are considered to be illustrative rather than restrictive. On the basis of the present invention, those skilled in the art can make some substitutions and modifications to some of the technical features according to the disclosed technical content without creative labor, all of which are within the protection scope of the present invention.

Claims

1. An isoxazoline hybridized neolignan compound, characterized in that: The isoxazoline hybridized neolignan compound is one of isoxazoline magnolol, isoxazoline and magnolol, isoxazoline nitrated magnolol, and isoxazoline nitrated and magnolol derivatives. The general chemical formula of the isoxazoline hybridized neolignan compound is shown in formula (I): In the formula (I), R 1 =OH or OMe; R 2 and R 3 =H or OH or OMe; R 4 =H or NO2; Ar is any of the following:

2. The method for preparing the isoxazoline hybridized neolignan compound according to claim 1, characterized in that: With triethylamine as a base and dichloromethane as a solvent, a raw material and α-chlorooxime are reacted in a 1,3-dipolar cycloaddition reaction to obtain an isoxazoline-hybridized neolignan compound; the raw material is one of magnolol, honokiol, nitrated magnolol and nitrated honokiol.

3. The preparation method according to claim 2, characterized in that: 1 mmol of the raw material was dissolved in 5 mL of dichloromethane, 5 mmol of triethylamine was added at 40°C, and then 4 mmol of α-chlorooxime was added to track and detect the reaction progress. After the reaction was completed, it was concentrated under reduced pressure and separated by preparative silica gel thin layer chromatography to obtain an isoxazoline hybridized neolignan compound.

4. The preparation method according to claim 2 or 3, characterized in that: The α-chlorooxime is one of α-chlorobenzaldehyde oxime, α-chloro-4-methylbenzaldehyde oxime, α-chloro-3,4-dimethylbenzaldehyde oxime, α-chloro-4-isopropylbenzaldehyde oxime, α-chloro-4-tert-butylbenzaldehyde oxime, α-chloro-2-naphthaldehyde oxime, α-chloro-3-cyanobenzaldehyde oxime, α-chloro-3,4-dichlorobenzaldehyde oxime, α-chloro-3-fluorobenzaldehyde oxime, α-chloro-4-chlorobenzaldehyde oxime or α-chloro-4-bromobenzaldehyde oxime.

5. The use of the isoxazoline hybridized neolignan compound in the preparation of insecticides as claimed in claim 1, characterized in that: The insecticide is applied to diamondback moth and oriental armyworm.

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