2,3-dihydrofuran derivatives, and methods of synthesis and use thereof

Abstract

The application discloses a 2,3-dihydrofuran derivative, and also discloses a synthesis method of the 2,3-dihydrofuran derivative, which takes an alpha-carbonyl cyclopropane amide compound as raw material, is dissolved in an organic solvent, and is subjected to intramolecular rearrangement cyclization reaction under the synergistic catalysis of an organic base and a bromide, so that the 2,3-dihydrofuran derivative is obtained at a very high yield; and the application of the 2,3-dihydrofuran derivative is also disclosed. The application has the advantages of high specificity, high conversion rate, only one product, good yield, and the like. The bioactivity test shows that the compound has moderate or excellent insecticidal activity, and has a good application prospect in the field of pesticides.

Description

Technical Field

[0001] The present invention belongs to the technical field of chemical synthesis, and in particular relates to a 2,3-dihydrofuran derivative and a synthesis method and application thereof. Background Art

[0002] 2,3-Dihydrofuran is a cyclic ether. As an important pharmacophore, it exists in many natural products and pesticide molecules. Compounds containing this type of structure have excellent insecticidal activity. For example, clairodine (1) isolated from larch has antifeedant and repellent activity against insects; azadirachtin (2) inhibits the release of peptide hormones related to ecdysone, thereby inhibiting the activity of ecdysone and affecting insect reproduction, molting, and pupation. At the same time, 2,3-dihydrofuran is also an important intermediate for the synthesis of highly active pesticides (such as oxalocarb and benfuracarb). Therefore, furan heterocycles are becoming one of the hot spots in the research and development of heterocyclic pesticides. The structural formulas of clairodine (1) and azadirachtin (2) are shown below.

[0003]

[0004] Over the years, the construction of 2,3-dihydrofuran skeleton has been developed rapidly and has achieved remarkable results. The preparation method has been reported many times. The common synthesis method includes transition metal or metal-free involved [1+4], [3+2], [3+1+1] cyclization reaction, etc. (Angew. Chem. Int. Ed. 2014, 53, 10223-10227; J. Org. Chem. 2008, 73, 7088-7095; J. Org. Chem. 2009, 74, 7403-7406). In addition, the reaction of efficiently constructing 2,3-dihydrofuran via intramolecular ring-opening-closing reaction process using α-carbonyl cyclopropane as substrate has also been involved. For example, in 2004, Akira's group used noble metal catalyst PdCl2(CH3CN)2 or Pd(PPh3)4 to catalyze the preparation of a series of 2,3-dihydrofuran from alkenyl cyclopropanone (J. Am. Chem. Soc. 2004, 126, 9645-9660); in 2006, Johnson's team synthesized 2,3-dihydrofuran derivatives by rearrangement reaction of 1-acyl-2-alkenyl cyclopropanone using Ni(COD)2 / PPh3 as catalyst (Org. Lett. 2006, 8, 573-576). However, up to now, the reaction conditions for synthesizing 2,3-dihydrofuran by rearrangement reaction of α-carbonyl cyclopropane are harsh, most of which need transition metal, noble metal and ligand, and the cost is high and the yield is low; and the α-carbonyl cyclopropane substrate needs multi-step pre-functionalization, and the substrate type is limited. On the other hand, the biological activity of the synthesized 2,3-dihydrofuran and its derivatives in the above methods has not been systematically analyzed and tested, and the application of such compounds in the field of pesticides has not been further explored. SUMMARY

[0005] To solve the above problems, the purpose of the present application is to provide a 2,3-dihydrofuran derivative, and to provide a synthesis method of the above-mentioned 2,3-dihydrofuran derivative and the application of the 2,3-dihydrofuran derivative.

[0006] To achieve the above-mentioned purpose of the application, the technical scheme adopted by the present application is as follows:

[0007] A 2,3-dihydrofuran derivative, having the structural formula:

[0008]

[0009] wherein, R 1 is selected from H or Me; Ar 1One selected from Ph, 4-MePh, 2-MePh, 4-ClPh, 4-MeOPh, 4-BrPh, 4-FPh, naphthyl, furyl, pyridyl, thiazolyl, biphenyl; Ar 2 One selected from Ph, 4-MePh, 2-MePh, 4-ClPh, 4-MeOPh, and 2,4-Me2Ph.

[0010] A method for synthesizing 2,3-dihydrofuran derivatives, wherein an α-carbonylcyclopropionamide compound A is used as a raw material, dissolved in an organic solvent, and subjected to an intramolecular rearrangement and cyclization reaction under the synergistic catalysis of an organic base and a bromide to obtain a 2,3-dihydrofuran derivative B in extremely high yield;

[0011] The reaction route is as follows:

[0012]

[0013] Among them, R 1 Selected from H or Me; Ar 1 One selected from Ph, 4-MePh, 2-MePh, 4-ClPh, 4-MeOPh, 4-BrPh, 4-FPh, naphthyl, furyl, pyridyl, thiazolyl, biphenyl; Ar 2 One selected from Ph, 4-MePh, 2-MePh, 4-ClPh, 4-MeOPh, 2,4-Me2Ph; R 2 One selected from CN, CH2CN, COOEt, CH2COOMe, COPh, COMe, COOH, and CH2Br.

[0014] Furthermore, the above-mentioned α-carbonyl cyclopropionamide compound A, organic solvent, organic base and bromide The dosage ratio is 1mmol:8~10mL:0.4~0.6mmol:0.8~1.0mmol.

[0015] Furthermore, the organic base is one of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 4-dimethylaminopyridine (DMAP), 1,5-diazabicyclo[4.3.0]-5-nonene (DBN), cinchonine, and quinuclidine.

[0016] Furthermore, the above-mentioned organic solvent is acetonitrile.

[0017] Furthermore, the rearrangement cyclization reaction temperature is 80-90°C.

[0018] Furthermore, the above rearrangement cyclization reaction time is 15 to 20 hours.

[0019] Furthermore, the above-mentioned synthesis method of 2,3-dihydrofuran derivatives uses thin layer chromatography (TLC) to monitor the reaction progress. After the reactant A completely disappears, water is added to the reaction system to stop the reaction, and then extraction is performed with an extractant. The organic phases are combined; the organic phases are dried with a desiccant, filtered, concentrated, and column chromatographed to obtain 2,3-dihydrofuran compound B.

[0020] Furthermore, the above-mentioned extractant is dichloromethane or ethyl acetate.

[0021] Furthermore, the organic phase desiccant is anhydrous sodium sulfate or anhydrous magnesium sulfate.

[0022] Another object of the present invention is to provide the use of the above-mentioned 2,3-dihydrofuran derivatives in the preparation of insecticides.

[0023] Furthermore, the above-mentioned insecticide is a drug for preventing and controlling broad bean aphids and cotton aphids.

[0024] Insecticidal activity test: The insecticidal activity of the 2,3-dihydrofuran derivatives of the present invention was tested by the immersion method. At a concentration of 300 μg / mL to 500 μg / mL, the 2,3-dihydrofuran compounds showed excellent insecticidal activity, causing the mortality rates of broad bean aphids and cotton aphids to be greater than 50%.

[0025] Due to the adoption of the above technical solution, the present invention has the following advantages:

[0026] The 2,3-dihydrofuran derivatives of the present invention have a raw material α-carbonylcyclopropionamide compound that is widely available and easy to obtain. In particular, the cooperative catalysts organic bases and bromides in the reaction are of various types, have a wide selection range, are low in cost, and do not need to be limited to harsh reaction conditions such as expensive precious metals. The entire reaction has strong specificity, a high conversion rate, and only one product with a good yield.

[0027] The method for synthesizing 2,3-dihydrofuran derivatives of the present invention is simple, has few steps, is easy to operate, has good substrate tolerance, mild reaction conditions, high yield and low cost, and the yield reaches 89-98%.

[0028] The biological activity test of the 2,3-dihydrofuran derivatives of the present invention shows that the compounds have moderate or excellent insecticidal activity and have good application prospects in the field of pesticides. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1 is the hydrogen spectrum of the target product B1 in Example 1;

[0030] Figure 2 is the carbon spectrum of the target product B1 in Example 1;

[0031] Figure 3 is the hydrogen spectrum of the target product B2 in Example 2;

[0032] Figure 4 is the carbon spectrum of the target product B2 in Example 2;

[0033] Figure 5 is the hydrogen spectrum of the target product B3 in Example 3;

[0034] Figure 6 This is the carbon spectrum of the target product B3 in Example 3. DETAILED DESCRIPTION

[0035] The present invention will be further described in detail with reference to the following examples; however, the following examples are merely illustrative, and the present invention is not limited to these examples.

[0036] Example 1

[0037] α-Carboxylcyclopropionamide compound A1 (0.29 g, 1 mmol) was dissolved in 10 mL of CH3CN, and then bromoacetonitrile (0.06 mL, 1 mmol) and DBU (0.06 mL, 0.4 mmol) were added thereto, and stirred in an 80°C oil bath for 15 h; the reaction was monitored by TLC, and after completion, 20 mL of water was added to quench the reaction; the mixture was extracted three times with dichloromethane (3×15 mL), the organic phases were combined, and then dried over anhydrous sodium sulfate, the dichloromethane was removed by vortexing, and the mixture was separated and purified by column chromatography to obtain 0.29 g of a white product B1 in a yield of 98%.

[0038] Specific reaction formula:

[0039]

[0040] Spectral data of compound B1:

[0041] 1 H NMR (CDCl3, 400MHz): δ: 3.05 (t, J=10.0Hz, 2H), 4.51 (t, J=10.0Hz, 2H), 7.03 (s, 1H ), 7.08-7.17(m, 1H), 7.21-7.34(m, 6H), 7.52-7.55(m, 4H), 7.84(d, J=16.0Hz, 1H);

[0042] 13C NMR (CDCl3, 100MHz): δ: 30.7, 69.2, 105.5, 116.5, 120.3, 124.2, 127.6, 128.7, 129.0, 136.2, 136.3, 138.1, 163.2, 163.5.

[0043] HRMS (ESI-TOF) calculation for C 19 H 18 NO2 + ([M+H] + ):292.1332,found:292.1336.

[0044] The hydrogen and carbon spectra of compound B1 are shown in Figure 1 、 Figure 2 .

[0045] The insecticidal activity of Compound B1 was tested using the immersion method. A 20 mg sample of Compound B1 was accurately weighed on an electronic balance and thoroughly dissolved in 1 g of acetone. A 0.05% (mass fraction) Tween 80 aqueous solution was added to prepare a 20 g stock solution. The solution was then diluted sequentially to 100 μg / mL, 200 μg / mL, 300 μg / mL, 400 μg / mL, and 500 μg / mL. Cut corn or cotton leaves (2.5 cm in diameter) were gently grasped with tweezers and thoroughly immersed in the solution for 10 seconds. The leaves were then placed on absorbent paper and allowed to air dry. The leaves were then placed in Petri dishes, with 16 uniformly distributed third-instar insects seeded into each dish. Each treatment was repeated three times, and the symptoms of poisoning of the test insects were observed. After 48 hours, it was found that when the concentration of the drug solution was 400 μg / mL, more than half of the test pests had died. Calculated based on the average of three times, the mortality rate of broad bean aphids reached 54%, and the mortality rate of cotton aphids was 61%; while in the control group, i.e., acetone and 0.05% (mass fraction) Tween 80 aqueous solution, no test insects died.

[0046] Example 2

[0047] α-Carboxylcyclopropionamide compound A2 (0.31 g, 1 mmol) was dissolved in 10 mL of CH3CN, and then ethyl bromoacetate (0.11 mL, 1 mmol) and DBU (0.07 mL, 0.5 mmol) were added thereto, and stirred in an 80°C oil bath for 15 h; the reaction was monitored by TLC, and after completion of the reaction, 20 mL of water was added to quench the reaction; the mixture was then extracted three times with dichloromethane (3×15 mL), the organic phases were combined, dried over anhydrous sodium sulfate, the dichloromethane was removed by vortexing, and the product was separated and purified by column chromatography to obtain 0.29 g of a white product B2 in a yield of 96%.

[0048] Specific reaction formula:

[0049]

[0050] Spectral data of compound B2:

[0051] 1 H NMR (CDCl3, 400MHz): δ: 2.31 (s, 3H), 3.04 (t, J = 8.0Hz, 2H), 4.51 (t, J = 10.0Hz, 2H), 6.97 (s, 1H), 7.11 -7.20(m,3H),7.25-7.34(m,3H),7.42(d,J=4.0Hz,2H),7.53(q,J=4.0Hz,2H),7.85(d,J=16.0Hz,1H);

[0052] 13 C NMR (CDCl3, 100MHz): δ: 20.9, 30.8, 69.1, 105.6, 116.6, 120.4, 127.6, 128.7, 128.9, 129.5, 133.8, 135.5, 136.1, 136.2, 162.9, 163.4.

[0053] HRMS (ESI-TOF) calculation for C 20 H 20 NO2 + ([M+H] + ):306.1489,found:306.1493.

[0054] The hydrogen and carbon spectra of compound B2 are shown in Figure 3 、 Figure 4 .

[0055] The insecticidal activity of Compound B2 was tested using an immersion method. A 20 mg sample of Compound B2 was accurately weighed on an electronic balance and thoroughly dissolved in 1 g of acetone. A 0.05% (mass fraction) Tween 80 aqueous solution was added to prepare a 20 g stock solution. The solution was then diluted to 100 μg / mL, 200 μg / mL, 300 μg / mL, 400 μg / mL, and 500 μg / mL concentrations. Cut corn or cotton leaves (2.5 cm in diameter) were gently grasped with tweezers and thoroughly immersed in the solution for 10 seconds. The leaves were then placed on absorbent paper and allowed to air dry. The leaves were then placed in Petri dishes, with 16 uniformly distributed third-instar insects seeded into each dish. Each treatment was repeated three times, and the symptoms of poisoning of the test insects were observed. After 48 hours, it was found that when the concentration of the drug solution was 500 μg / mL, more than half of the test pests had died. Calculated based on the average of three times, the mortality rate of broad bean aphids reached 58%, and the mortality rate of cotton aphids was 66%; while in the control group, i.e., acetone and 0.05% (mass fraction) Tween 80 aqueous solution, no test insects died.

[0056] Example 3

[0057] α-Carboxylcyclopropionamide compound A3 (0.29 g, 1 mmol) was dissolved in 10 mL of CH3CN, and then bromoacetone (0.08 mL, 1 mmol) and DBU (0.06 mL, 0.4 mmol) were added and stirred in an 85°C oil bath for 16 h. The reaction was monitored by TLC. After completion of the reaction, 20 mL of water was added to quench the reaction. The mixture was then extracted three times with dichloromethane (3 × 15 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, and the dichloromethane was removed by vortexing. The product was separated and purified by column chromatography to obtain 0.26 g of a white product B3 with a yield of 90%.

[0058] Specific reaction formula:

[0059]

[0060] Spectral data of compound B3:

[0061] 1 H NMR (CDCl3, 400MHz): δ: 3.09 (t, J = 10.0Hz, 2H), 4.53 (t, J = 10.0Hz, 2H), 7.07-7.22 (m, 4H),7.29-7.33(m,2H),7.50-7.64(m,4H),8.13(d,J=16.0Hz,1H),8.57-8.59(m,1H);

[0062] 13 C NMR (CDCl3, 100MHz): δ: 30.9, 69.3, 107.7, 120.3 (2C), 122.3, 122.9, 124.2, 128.9, 135.5, 136.3, 138.1, 149.8, 154.9, 162.1, 163.2.

[0063] HRMS (ESI-TOF) calculation for C 18 H 17 N2O2 + ([M+H] + ):293.1285,found:293.1288.

[0064] The hydrogen and carbon spectra of compound B3 are shown in Figure 5 、 Figure 6 .

[0065] The insecticidal activity of Compound B3 was tested using the immersion method. A 20 mg sample of Compound B3 was accurately weighed on an electronic balance and thoroughly dissolved in 1 g of acetone. A 0.05% (mass fraction) Tween 80 aqueous solution was added to prepare a 20 g stock solution. The solution was then diluted sequentially to 100 μg / mL, 200 μg / mL, 300 μg / mL, 400 μg / mL, and 500 μg / mL. Cut corn or cotton leaves (2.5 cm in diameter) were gently grasped with tweezers and thoroughly immersed in the solution for 10 seconds. The leaves were then placed on absorbent paper and allowed to air dry. The leaves were then placed in Petri dishes, with 16 uniformly distributed third-instar insects seeded into each dish. Each treatment was repeated three times, and the symptoms of poisoning of the test insects were observed. After 48 hours, it was found that when the concentration of the drug solution was 400 μg / mL, more than half of the test pests had died. Calculated based on the average of three times, the mortality rate of broad bean aphids reached 68%, and the mortality rate of cotton aphids was 64%; while in the control group, i.e., acetone and 0.05% (mass fraction) Tween 80 aqueous solution, no test insects died.

[0066] Example 4

[0067] α-Carboxylcyclopropionamide compound A4 (0.30 g, 1 mmol) was dissolved in 10 mL of CH3CN, and then 2-bromoacetophenone (0.20 g, 1 mmol) and DMAP (0.07 g, 0.6 mmol) were added and stirred in an oil bath at 90°C for 20 h. The reaction was monitored by TLC. After completion, 20 mL of water was added to quench the reaction. The product was then extracted three times with ethyl acetate (3 × 15 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, and the ethyl acetate was removed by vortexing. The product was then purified by column chromatography to obtain 0.28 g of a white product B4 in a yield of 93%.

[0068] Specific reaction formula:

[0069]

[0070] Spectral data of compound B4:

[0071] 1 H NMR (DMSO-d6, 400MHz): δ: 3.16 (t, J = 10.0Hz, 2H), 4.52 (t, J = 8.0Hz, 2H), 7.06 (t, J = 8.0Hz, 1H), 7. 29-7.37(m,3H),7.53(d,J=16.0Hz,1H),7.68(d,J=8.0Hz,2H),8.08(s,1H),9.08(d,J=4.0Hz,2H);

[0072] 13C NMR (DMSO-d6, 100 MHz): δ: 30.8, 69.9, 109.0, 119.7, 121.2, 123.9, 124.8, 128.8, 137.1, 139.5, 145.1, 155.2, 160.5, 163.5.

[0073] HRMS (ESI-TOF) calcd for C 16 H 15 N2O2S + ([M+H] + ): 299.0849, found: 299.0851.

[0074] The insecticidal activity test of the above compound B4: using the immersion method. 20 mg of compound B4 sample was accurately weighed on an electronic balance, dissolved in 1 g of acetone, and then diluted into 20 g of sample mother liquor by adding 0.05% (mass fraction) Tween 80 aqueous solution, and then diluted into 100 μg / mL, 200 μg / mL, 300 μg / mL, 400 μg / mL, 500 μg / mL of drug solution in turn. The cut corn leaf (diameter 2.5 cm) or cotton leaf was gently clamped with tweezers, immersed in the drug solution for 10 s, placed on the water absorption paper, and then placed in the culture dish after natural air drying. 16 heads of uniform 3rd instar test insects were introduced into each dish. Each treatment had 3 replicates, and the insect poisoning symptoms were observed. After 48 h, it was found that when the drug concentration was 300 μg / mL, more than half of the test insects died, and the mortality rate of the vetch aphid reached 63%, and the mortality rate of the cotton aphid reached 66%. The control group, i.e. acetone and 0.05% (mass fraction) Tween 80 aqueous solution, had a test insect mortality rate of only 2%.

[0075] Example 5

[0076] Take α-carbonyl cyclopropylamide compound A5 (0.34 g, 1 mmol) and dissolve it in 10 mL of CH3CN, then add 1,2-dibromoethane (0.07 mL, 0.8 mmol) and DBN (0.07 g, 0.6 mmol) to it, and stir in a 90°C oil bath pot for 20 h; TLC detects the reaction, and after the reaction is complete, quench the reaction with 20 mL of water; then extract three times with dichloromethane (3 x 15 mL), combine the organic phases, dry over anhydrous magnesium sulfate, spin off the dichloromethane, and column chromatography separation and purification to obtain white product B5 0.30 g with a yield of 89%.

[0077] The specific reaction formula is:

[0078]

[0079] The spectrum data of compound B5 is:

[0080] 1 H NMR (CDC13, 400 MHz): δ: 3.14 (t, J = 8.0 Hz, 2H), 4.62 (t, J = 8.0 Hz, 2H), 6.98 (s, 1H), 7.11 (t, J = 8.0 Hz, 1H), 7.34 (t, J = 8.0 Hz, 2H), 7.44-7.57 (m, 5H), 7.81-7.90 (m, 3H), 7.94 (d, J = 16.0 Hz, 1H), 8.05 (d, J = 16.0 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H);

[0081] 13 C NMR (CDC13, 100 MHz): δ: 30.9, 69.2, 105.6, 118.8, 120.2, 123.4, 124.2, 124.7, 125.6, 125.8, 126.3, 128.7, 129.0, 129.3, 131.5, 132.9, 133.2, 133.7, 138.1, 163.3, 163.4.

[0082] HRMS (ESI-TOF) calcd for C 23 H 20 NO2 + ([M+H] + ): 342.1489, found: 342.1483.

[0083] The insecticidal activity test of the above-mentioned compound B5: using the immersion method; 20 mg of compound B5 sample was accurately weighed on an electronic balance, dissolved with 1 g of acetone, and then diluted with 0.05% (mass fraction) Tween 80 aqueous solution to prepare a 20 g sample mother liquor, and then sequentially diluted to 100 μg / mL, 200 μg / mL, 300 μg / mL, 400 μg / mL, and 500 μg / mL of the pesticide solution. The cut corn leaves (diameter 2.5 cm) or cotton leaves were gently clamped with tweezers, immersed in the pesticide solution for 10 s, placed on the water absorption paper, and then naturally dried, and then placed in a culture dish, and 16 heads of uniform 3rd instar test insects were introduced into each dish. Each treatment had 3 replicates, the poisoning symptoms of the test insects were observed, and after 48 h, it was found that when the pesticide concentration was 400 μg / mL, the mortality of the test insects was more than half, and the mortality of the aphids was 55%, and the mortality of the cotton aphids was 58%; the control group, i.e. acetone and 0.05% (mass fraction) Tween 80 aqueous solution, had a test insect mortality of 4%.

[0084] Example 6

[0085] α-Carboxylcyclopropionamide compound A6 (0.34 g, 1 mmol) was dissolved in 8 mL of CH3CN, and then bromoacetic acid (0.12 g, 0.9 mmol) and cinchoninic acid (0.12 g, 0.4 mmol) were added. The mixture was stirred in an 80°C oil bath for 17 h. The reaction was monitored by TLC. After completion, 20 mL of water was added to quench the reaction. The mixture was then extracted three times with dichloromethane (3 × 15 mL). The organic phases were combined, dried over anhydrous sodium sulfate, and the dichloromethane was removed by vortexing. The product was then purified by column chromatography to obtain 0.28 g of a white product B6 in a yield of 91%.

[0086] Specific reaction formula:

[0087]

[0088] Spectral data of compound B6:

[0089] 1 H NMR (CDCl3, 400MHz): 1.49 (d, J = 8.0Hz, 3H), 2.68 (dd, J = 12.0Hz, 8.0Hz, 1H), 3.20 (dd, J = 12.0Hz, 8.0Hz, 1H), 4.87-4.93 (m, 1H),6.96(s,1H),7.08-7.12(m,1H),7.20(d,J=16.0Hz,1H),7.28-7.35(m,5H),7.53-7.56(m,4H),7.85(d,J=16.0Hz,1H);

[0090] 13 C NMR (CDCl3, 100MHz): 21.9, 37.9, 77.6, 104.8, 116.8, 120.3, 124.1, 127.6, 128.6, 128.9, 129.0, 136.2, 138.1, 162.5, 163.7.

[0091] HRMS (ESI-TOF) calculation for C 20 H 20 NO2 + ([M+H] + ):306.1489,found:306.1493.

[0092] The insecticidal activity test of the compound B6 is as follows: 20 mg of the compound B6 sample is accurately weighed on an electronic balance, dissolved in 1 g of acetone, and then diluted with 0.05% (mass fraction) Tween 80 solution to prepare a 20 g sample mother liquor, and then sequentially diluted to 100 μg / mL, 200 μg / mL, 300 μg / mL, 400 μg / mL, and 500 μg / mL of the pesticide solution. The corn leaves (2.5 cm in diameter) or cotton leaves are immersed in the pesticide solution of different concentrations, and then taken out and dried with a tweezers. The dried corn leaves or cotton leaves are placed in a culture dish, 16 insects are introduced, and 3 repeats are performed for each treatment. The insect poisoning symptoms are observed, and after 48 h, it is found that when the concentration of the pesticide solution is 500 μg / mL, the death number of the test insects is more than half, and the mortality of the aphids reaches 63%, and the mortality of the cotton aphids is 60%; and the control group, i.e., the acetone and 0.05% (mass fraction) Tween 80 solution, has no insect death.

[0093] The above merely describes the preferred embodiments of the present application, but should not be used to limit the present application, and any modification, equivalent replacement, and improvement within the spirit and principle of the present application should be included in the protection scope of the present application.

Claims

1. Use of a 2,3-dihydrofuran derivative in the preparation of an insecticide, characterized in that: The structural formula of 2,3-dihydrofuran derivatives is: Among them, R 1 Selected from H or Me; Ar 1 One selected from Ph, 4-MePh, 2-MePh, 4-ClPh, 4-MeOPh, 4-BrPh, 4-FPh, naphthyl, furyl, pyridyl, thiazolyl, biphenyl; Ar 2 One selected from Ph, 4-MePh, 2-MePh, 4-ClPh, 4-MeOPh, and 2,4-Me2Ph.

2. The use according to claim 1, characterized in that: The insecticide is a medicine for preventing and controlling broad bean aphids and cotton aphids.

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