Preparation and application of alpha-hydroxyl-(alpha-diaryl) acetamide compound

Abstract

The invention discloses a preparation method of an alpha-hydroxyl-(alpha-diaryl) acetamide compound and an application of the alpha-hydroxyl-(alpha-diaryl) acetamide compound in inhibition of seed germination, the compound can significantly inhibit seed germination, in addition, the compound has a superstrong inhibition effect on root growth, and the inhibition rate of the compound is as high as 92%. The preparation method of the alpha-hydroxyl-(alpha-diaryl) acetamide compound is simple to operate, can be easily realized through commercialized diaryl ethanone and amino compounds, and has the advantages of high efficiency, simple steps, mild conditions, wide substrate application range, simple post-treatment and the like. Powerful technical support is expected to be provided for deep development and application in the fields of medicine, agriculture and the like.

Description

TECHNICAL FIELD

[0001] The present application relates to acetamide compounds, in particular, to a preparation method of an alpha-hydroxy-(alpha-diaryl)acetamide compound and its application in inhibiting seed germination activity and rhizome growth. BACKGROUND

[0002] Agricultural development is directly related to national food security and the "rice bag" and "vegetable basket" of the people. Weeds in farmland have a huge impact on the quality and yield of agricultural products, and have become one of the most serious biological threats to food security. Weeds are plants that grow in places harmful to human survival and activities. Agricultural field weeds compete with crops for nutrients, water, sunlight and space, and hinder ventilation and light transmission in the field, thereby reducing crop yield and quality. Many weeds are intermediate hosts or habitats for pathogenic microorganisms and pests, which can cause diseases and insect pests.

[0003] Herbicides play an irreplaceable role in ensuring stable agricultural production and income and national food security. However, with the widespread and frequent use of herbicides, weed resistance problems are becoming increasingly serious worldwide. The development of new green herbicides with high efficiency, low toxicity and environmental friendliness is one of the effective ways to solve the current problem of weed resistance development.

[0004] Alpha-hydroxy-(alpha-diaryl)acetamide is a very important organic molecular skeleton, which is widely present in the structures of many compounds with biological activity and pharmacological activity (Journal of Enzyme Inhibition & Medicinal Chemistry, 2009, 24(4): 1015-1023.; Monatshefte fuer Chemie / Chemical Monthly 137(6): 795-801). This structural unit has important application potential in the fields of pharmaceutical research and development (such as enzyme inhibitors) and agricultural chemical development. The existing methods for constructing such a skeleton usually involve multi-step synthesis routes, which are complicated, time-consuming, and often have specific limitations on substrate structure (limited structural diversity), resulting in poor universality. SUMMARY

[0005] In view of the problem of the development of new green herbicides with high efficiency, low toxicity and environmental friendliness, the present application provides a preparation method of alpha-hydroxy-(alpha-diaryl)acetamide compounds and its application in inhibiting seed germination activity and rhizome growth. These compounds can provide a reference for the discovery of new herbicide lead structure compounds.

[0006] In order to achieve the above object, the present application provides, in one aspect, an application of an α-hydroxy-(α-diaryl)acetamide compound in the preparation of a medicine for inhibiting seed germination activity and rhizome growth, and the structural formula of the compound is shown in formula (1):

[0007] Formula (1) In the formula, R and R1 are each independently selected from H, C1-C 20 alkyl, an aromatic group, halogen, hydroxyl, thiol, trifluoromethyl, nitro, an ether bond or a thioether bond; R2 and R3 are each independently selected from H, alkyl, an aromatic group or a heterocycle.

[0008] The compound can inhibit the synthesis of endogenous auxin and gibberellin in plants, as well as the polar conduction and lateral transport of auxin, and has a significant regulating effect on seed germination and root and stem growth.

[0009] Specifically, the minimum inhibitory concentration of the α-hydroxy-(α-diaryl)acetamide compound is 1 ppm.

[0010] The second aspect of the present application provides a preparation method of the above-mentioned α-hydroxy-(α-diaryl)acetamide compound, which comprises: dissolving a diarylacetone compound and an amino compound in a solvent, adding a base reagent and a catalyst, and reacting at 150-180°C for 20-24 h to obtain the α-hydroxy-(α-diaryl)acetamide compound.

[0011] The reaction mechanism is shown as follows:

[0012] First, the diarylacetone compound is condensed with the amino compound to form an imine compound (Int-A), and then the imine intermediate is oxidized in the reaction to obtain a key intermediate Int-B. The intermediate Int-B undergoes a nucleophilic addition in the presence of a protonic acid (catalyst) and rearrangement with diphenylacetic acid, and then the α-hydroxy-(α-diaryl)acetamide is obtained.

[0013] The reaction design of the present application is very ingenious, and the construction of the amide group is realized by using a simple diphenyl ketone compound, which discards the traditional route of using carboxylic acid, carboxylic acid ester and acyl chloride. In addition, the hydroxyl group can be easily constructed at the α position, avoiding halogenation or using a strong oxidizing agent. Through this idea, the present application can construct the hydroxyl group and the amide functional group at one time.

[0014] Preferably, the amino compound is selected from aniline, benzylamine, o-methylaniline, m-methylaniline, p-methylaniline, trifluoromethoxyaniline, p-fluoroaniline, p-chloroaniline, p-bromoaniline, p-trifluoromethylaniline, m-trifluoromethylaniline, o-methylaniline, p-phenylaniline, naphthylamine, acetylene aniline, cyclohexylamine, p-nitroaniline, methyl p-formate aniline, ethyl p-formate aniline, p-cyanoaniline, 4-aminopyridine, 3-aminopyrimidine, aminoquinoline, 2-aminobenzothiazole, N-methylaniline, N-phenylbenzamide, octylamine, ammonia, and 3,3-diphenylpropylamine.

[0015] The diaryl ethyl ketone compounds are selected from diphenyl ethyl ketone, o-tolyl-2-phenyl-ethane, m-tolyl-2-phenyl-ethane, p-tolyl-2-phenyl-ethane, p-fluorophenyl-2-phenyl-ethane, p-chlorophenyl-2-phenyl-ethane, p-bromophenyl-2-phenyl-ethane, p-trifluoromethylphenyl-2-phenyl-ethane, p-methylphenyl-2-tolyl-ethane, p-hydroxyphenyl-2-phenyl-ethane, p-mercaptophenyl-2-phenyl-ethane, p-methoxyphenyl-2-phenyl-ethane, and (2-naphthyl)-2-phenyl-ethane.

[0016] The alkaline reagent is selected from one or more of cesium carbonate, potassium carbonate, potassium hydroxide, potassium tert-butoxide, potassium phosphate, potassium hydroxide, sodium bicarbonate, sodium hydroxide, and potassium bicarbonate.

[0017] The catalyst is selected from AlCl3, CuCl, AgCl, Ag2CO3, Ag2O, Cu(OTf)2, and Cu(OAc)2.

[0018] The solvents are DMF (N,N-dimethylformamide), DMA (dimethylacetamide), toluene, and NMP (methylpyrrolidone).

[0019] Preferably, the molar ratio of the diaryl ethyl ketone compound, the amino compound, the base reagent, and the catalyst is 1:(1.1~1.3):(1.5~2):(0.02~0.03).

[0020] Furthermore, after the reaction is complete, water is added to quench the reaction system, then the pH is adjusted to 5-6, and finally extraction, washing, drying and purification are performed to obtain pure α-hydroxy-(α-diaryl)acetamide compounds.

[0021] Through the above technical solution, the present invention achieves the following beneficial effects: 1. The compound synthesized in this invention can significantly inhibit seed germination and also exhibits a strong inhibitory effect on root growth, with an inhibition rate as high as 92%.

[0022] 2. The preparation method of the α-hydroxy-(α-diaryl)acetamide compounds of this invention is simple to operate and can be easily achieved using commercially available diaryl acetones and amino compounds. It has advantages such as high efficiency, simple steps, mild conditions, wide substrate applicability, and simple post-processing. It is expected to provide strong technical support for in-depth development and application in the fields of medicine and agriculture. Detailed Implementation

[0023] The specific embodiments of the present invention will be described in detail below with reference to examples. It should be understood that the specific embodiments described herein are for illustration and explanation only and are not intended to limit the present invention.

[0024] Unless otherwise specified, all reagents used in the following examples are commercially available products.

[0025] Example 1

[0026] Add aniline (1.2 mmol, 1.0 equiv.), diphenyl ethyl ketone (1.0 mmol, 1.0 equiv.), cesium carbonate (2.0 mmol, 2.0 equiv.), aluminum chloride (0.003 g, 2.5 mmol%) and 4 mL DMF to a 50 mL round-bottom flask. Place the resulting mixture in an oil bath at 150 °C, add a stir bar, and heat with magnetic stirring to allow it to react completely for 24 h.

[0027] After the reaction was completed, the round-bottom flask was cooled to room temperature, and 20 mL of water was added to quench the reaction system. Dilute HCl solution (1 mol / L) was added dropwise to neutralize the pH of the reaction solution to about 5-6. Then, ethyl acetate (EtOAc) was used for extraction, followed by washing the organic phase three times with saturated brine. After washing, all organic phases were combined and dried with an appropriate amount of anhydrous magnesium sulfate. The solvent was then evaporated using a rotary evaporator to obtain the crude product α-hydroxy-(α-diaryl)acetamide compounds. Finally, the product (0.435 g, 90%) was separated by silica gel column chromatography using petroleum ether:ethyl acetate in a ratio of 25:4 as the developing solvent.

[0028] 3a: 1 H NMR (400 MHz, CDCl3) δ 8.53 (s, 1H), 7.54 (d, J = 7.9 Hz, 2H), 7.50-7.45 (m, 4H), 7.36-7.28 (m, 8H), 7.11 (t, J = 7.5 Hz, 1H), 3.71 (s, 1H). 13C NMR (100 MHz, CDCl3) δ 171.11, 142.60, 137.21, 129.07, 128.48, 128.38,127.61, 124.77, 119.81, 81.95. Example 2

[0029] The preparation was carried out according to the method of Example 1, except that aniline in the reaction was replaced with an equivalent amount of benzylamine. The final product 3b (0.621 g, 87%) was obtained.

[0030] 3b: 1 H NMR (400 MHz, CDCl3) δ 7.41-7.35 (m, 4H), 7.31-7.19 (m, 9H), 7.17- 7.12 (m, 2H), 6.91 (t, J = 5.9 Hz, 1H), 4.39 (d, J = 5.9 Hz, 2H), 4.02(s, 1H). 13 C NMR (100 MHz, CDCl3) δ 173.28, 142.88, 137.82, 128.74, 128.33,128.14, 127.61, 127.59, 81.54, 43.83. Example 3

[0031] The preparation was carried out according to the method of Example 1, except that aniline in the reaction was replaced with an equivalent amount of o-methylaniline, the base reagent was replaced with an equivalent amount of potassium carbonate, and the solvent was replaced with DMA. The final product 3c (0.246 g, 81%) was obtained.

[0032] 3C: 1 H NMR (600 MHz, CDCl3) δ 8.13 (s, 1H), 8.05 (d, J = 8.0 Hz, 1H), 7.57-7.48 (m, 4H), 7.45-7.34 (m, 7H), 7.21 (d, J = 8.3 Hz, 1H), 7.14 (d, J =6.6 Hz, 1H), 7.06 (t, J = 7.4 Hz, 1H), 3.95 (s, 1H), 2.02 (s, 4H). Example 4

[0033] The product was prepared according to the preparation method of Example 3, except that o-methylaniline in the reaction was replaced with an equivalent amount of m-methylaniline, and the final product 3d (0.301g, 95%) was obtained.

[0034] 3d: 1 H NMR (600 MHz, CDCl3)δ 8.46 (s, 1H), 7.53-7.44 (m, 4H), 7.42 (s,1H), 7.33 (tt, J1 = 14.2, J2 = 7.1 Hz, 7H), 7.18 (t, J = 7.8 Hz, 1H), 6.93(d, J = 7.5 Hz, 1H), 3.70 (s, 1H), 2.31 (s, 3H); 13 C NMR (150 MHz, CDCl3) δ170.99, 142.57, 138.99, 136.98, 129.44, 128.58, 127.74, 127.28, 126.47,81.87, 22.23. Example 5

[0035] The product was prepared according to the preparation method of Example 3, except that o-methylaniline in the reaction was replaced with an equivalent amount of p-methylaniline to obtain the final product 3e (0.281 g, 89%).

[0036] 3e: 1 H NMR (600 MHz, CDCl3) δ 8.42 (s, 1H), 7.48-7.46 (m, 4H), 7.42-7.40 (m, 2H), 7.37-7.33 (m, 6H), 7.12-7.10 (m, 2H), 3.73 (s, 1H), 2.30 (s,3H); 13 C NMR (150 MHz, CDCl3, ppm) δ 170.89, 142.60, 134.57, 134.37, 128.40,127.65, 127.55, 119.74, 81.82, 20.86. Example 6

[0037] The product was prepared according to the preparation method of Example 3, except that p-methylaniline in the reaction was replaced with an equivalent amount of p-trifluoromethoxyaniline to obtain the final product 3f (0.332 g, 84%).

[0038] 3f: 1 H NMR (600 MHz, CDCl3) δ 8.65 (s, 1H), 7.53-7.51 (m, 2H), 7.48-7.47 (m, 4H), 7.37-7.36 (m, 6H), 7.28-7.27 (m, 2H), 3.44(s, 1H). 13 C NMR (150MHz, CDCl3) δ 170.99, 142.33, 135.76, 129.15, 128.75, 128.25, 127.48, 127.22,120.95, 81.95. Example 7

[0039] The preparation was carried out according to the method of Example 1, except that aniline in the reaction was replaced with 1.5 equivalents of p-fluoroaniline, aluminum chloride was replaced with an equal amount of CuCl, the alkali was replaced with an equivalent amount of potassium carbonate, and the solvent was replaced with DMA. 3 g (0.257 g, 87%) of the final product was obtained.

[0040] 3g: 1 H NMR (600 MHz, CDCl3) δ 8.55 (s, 1H), 7.59-7.44 (m, 6H), 7.43-7.32 (m, 6H), 7.01 (t, J = 8.7 Hz, 2H), 3.49 (s, 1H). Example 8

[0041] The preparation was carried out according to the preparation method of Example 7, except that the p-fluoroaniline in the reaction was replaced with an equivalent amount of p-chloroaniline, and the final product 3h (0.253g, 83%) was obtained.

[0042] 3h: 1 H NMR (600 MHz, CDCl3) δ 8.65 (s, 1H), 7.53-7.51 (s, 2H), 7.48-7.47 (m, 4H), 7.37-7.36 (m, 6H), 7.28-7.27 (s, 2H), 3.44(s, 1H). 13C NMR (150MHz, CDCl3) δ 170.99, 142.33, 135.76, 129.15, 128.75, 128.25, 127.48, 127.22,120.95, 81.95. Example 9

[0043] The product was prepared according to the preparation method of Example 7, except that p-fluoroaniline in the reaction was replaced with an equivalent amount of p-bromoaniline to obtain the final product 3i (0.289 g, 80%).

[0044] 3i: 1 H NMR (300 MHz, CDCl3) δ 8.63 (s, 1H), 7.55-7.46 (m, 6H), 7.44 (s, 2H), 7.42-7.32 (m, 6H), 3.40 (s, 1H). Example 10

[0045] The product was prepared according to the preparation method of Example 7, except that p-fluoroaniline in the reaction was replaced with an equivalent amount of p-trifluoromethylaniline to obtain the final product 3j (0.526 g, 86%).

[0046] 3j: 1 H NMR (500 MHz, CDCl3) δ 8.94 (s, 1H), 8.09 (s, 0.5H), 7.80 (d, J= 7.7 Hz, 1H), 7.75-7.63 (m, 3H), 7.57- 7.54 (m, 4H), 7.46 (s, 5H), 7.24 (s,0.5H), 3.60 (s, 1H). 13 C NMR (125 MHz, CDCl3) δ 171.43, 142.23, 140.26, 132.28, 128.52, 127.99, 127.52, 126.30, 119.84, 119.47, 82.09. Example 11

[0047] The product was prepared according to the preparation method of Example 11, except that p-trifluoromethylaniline in the reaction was replaced with an equivalent amount of m-trifluoromethylaniline, and the final product 3k (0.531 g, 87%) was obtained.

[0048] 3k: 1 H NMR (500 MHz, CDCl3) δ 8.91 (s, 1H), 7.89 (s, 1H), 7.69 (s, 1H), 7.53-7.26 (m, 13H). 13 C NMR (126 MHz, CDCl3) δ 171.42, 142.26, 137.79, 131.46,129.59, 128.49, 127.55, 124.92, 122.84, 121.25, 116.57, 116.54, 82.03. Example 12

[0049] The preparation was carried out according to the method of Example 1, except that aniline in the reaction was replaced with an equivalent amount of o-methylaniline, aluminum chloride was replaced with an equal amount of AgCl, the base reagent was replaced with an equivalent amount of potassium hydroxide, and the solvent was replaced with toluene. 3l (0.357g, 88%) of the final product was obtained.

[0050] 3l: 1 H NMR (500 MHz, CDCl3) δ 8.98 (s, 1H), 8.41 (d, J = 7.8 Hz, 1H), 7.48 (d, J = 7.2 Hz, 4H), 7.33 (d, J = 8.6 Hz, 6H), 7.03 (d, J = 8.0 Hz, 1H), 6.95 (d, J = 8.2 Hz, 1H), 6.82 (d, J = 7.9 Hz, 1H), 3.98 (s, 1H), 3.73 (s, 3H). 13 C NMR (125 MHz, CDCl3) δ 171.11, 148.42, 142.88, 128.42, 128.23, 127.67,127.04, 124.38, 121.12, 119.55, 110.17, 82.11, 55.79. Example 13

[0051] The preparation was carried out according to the method of Example 1, except that aniline in the reaction was replaced with an equivalent amount of p-phenylaniline, aluminum chloride was replaced with an equal amount of Ag2CO3, the alkaline reagent was replaced with an equivalent amount of potassium hydroxide, and the solvent was replaced with toluene. The final product 3m (0.982 g, 90%) was obtained.

[0052] 3m: 1 H NMR (400 MHz, CDCl3) δ 8.67 (s, 1H), 7.61 (d, J = 8.4 Hz, 2H), 7.57-7.51 (m, 4H), 7.48 (dd, J = 7.3, 2.6 Hz, 4H), 7.40 (t, J = 7.5 Hz, 2H),7.37-7.30 (m, 7H), 3.76 (s, 1H). 13 C NMR (100 MHz, CDCl3) δ 171.19, 142.59,140.44, 137.65, 136.52, 128.84, 128.50, 128.40, 127.68, 127.65, 127.24,126.91, 120.14, 82.00. Example 14

[0053] The product was prepared according to the preparation method of Example 13, except that p-phenylaniline in the reaction was replaced with an equivalent amount of naphthylamine to obtain the final product 3n (0.779 g, 83%).

[0054] 3n: 1 H NMR (400 MHz, CDCl3) δ 8.89 (s, 1H), 8.15 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 7.8 Hz, 1H), 7.68 (d, J = 8.3 Hz, 1H), 7.58 (d, J = 7.1 Hz, 4H),7.51-7.34 (m, 10H), 3.97 (s, 1H). 13 C NMR (100 MHz, CDCl3) δ 171.66, 142.74,134.04, 131.62, 128.88, 128.62, 128.48, 127.68, 126.46, 126.02, 125.82,125.71, 119.82, 119.34, 82.32. Example 15

[0055] The preparation was carried out according to the method of Example 1, except that aniline in the reaction was replaced with 2 equivalents of p-acetyleneaniline, aluminum chloride was replaced with an equal amount of Ag₂O, the base reagent was replaced with an equivalent amount of potassium tert-butoxide, and the solvent was replaced with toluene. The final product 3o (0.532 g, 81%) was obtained.

[0056] 3o: 1 H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 7.56 (d, J = 8.6 Hz, 2H), 7.53-7.42 (m, 6H), 7.42-7.32 (m, 6H), 3.48 (s, 1H), 3.05 (s, 1H). Example 16

[0057] The product was prepared according to the preparation method of Example 15, except that p-acetylene aniline in the reaction was replaced with an equivalent amount of cyclohexylamine to obtain the final product 3p (0.408 g, 98%).

[0058] 3p: 1 H NMR (400 MHz, CDCl3) δ 7.42-7.35 (m, 4H), 7.34-7.28 (m, 6H), 6.27 (d, J = 8.3 Hz, 1H), 4.17 (s, 1H), 3.83-3.71 (m, 1H), 1.89-1.82 (m, 2H),1.67-1.51 (m, 3H), 1.40-1.26 (m, 2H), 1.17 -1.04 (m, 3H). 13 C NMR (100 MHz, CDCl3) δ 172.28, 143.10, 128.28, 128.02, 127.56, 81.22, 48.75, 32.77, 25.43,24.63. Example 17

[0059] The product was prepared according to the preparation method of Example 15, except that p-acetylene aniline in the reaction was replaced with an equivalent amount of p-nitroaniline to obtain the final product 3q (0.334, 84%).

[0060] 3q: 1H NMR (400 MHz, CDCl3) δ 9.21 (s, 1H), 8.21-8.18 (m, 2H), 7.79-7.75(m, 2H), 7.50-7.38(m, 4H), 7.37-7.27(m, 6H), 3.37(s, 1H). 13 C NMR (100 MHz, CDCl3) δ 171.48, 143.74, 142.96, 141.86, 128.54, 127.41, 125.03, 119.24,88.17. Example 18

[0061] The product was prepared according to the preparation method of Example 1, except that the aniline in the reaction was replaced with an equivalent amount of methyl paraformate aniline, and the final product 3r (0.267, 84%) was obtained.

[0062] 3r: 1 H NMR (400 MHz, CDCl3) δ 8.93 (s, 1H), 7.80-7.97 (m, 2H), 7.65 (s,2H), 7.49-7.47 (m, 4H), 7.37-7.34 (m, 6H), 3.87 (s, 3H), 3.61 (s, 1H). 13 C NMR (100 MHz, CDCl3) δ 171.28, 166.53, 142.21, 141.31, 128.44, 127.48, 125.91,118.90, 82.02, 52.03. Example 19

[0063] The product was prepared according to the preparation method of Example 1, except that the aniline in the reaction was replaced with an equivalent amount of ethyl p-formate aniline, and the final product 3s (0.267, 84%) was obtained.

[0064] 3s: 1 H NMR (400 MHz, CDCl3) δ 8.96 (s, 1H), 7.98-7.96 (m, 2H), 7.64-7.62 (m, 2H), 7.49-7.46 (m, 4H), 7.37-7.34 (m, 6H), 4.35-4.29 (m, 2H), 3.72(s, 1H), 1.36 (t, J=7.8 Hz, 3H). 13 C NMR (100 MHz, CDCl3) δ 171.29, 166.09, 142.23, 141.24, 128.40, 127.49, 126.22, 118.66, 81.99, 60.91, 14.28. Example 20

[0065] The preparation was carried out according to the method of Example 1, except that aniline in the reaction was replaced with an equivalent amount of p-cyanoaniline, aluminum chloride was replaced with an equivalent amount of Cu(OTf)2, the base reagent was replaced with an equivalent amount of potassium tert-butoxide, and the solvent was replaced with DMA. The final product 3t (0.333, 85%) was obtained.

[0066] 3t: 1 3.76 (s,1H). 13 C NMR (100 MHz, CDCl3) δ 173.35, 144.17, 143.32, 133.37, 128.14, 128.11,127.62, 119.23, 118.45, 105.04, 79.79. Example 21

[0067] The product was prepared according to the preparation method of Example 19, except that p-cyanoaniline in the reaction was replaced with an equivalent amount of 4-aminopyridine to obtain the final product 3u (0.254, 87%).

[0068] 3u: 1H NMR (400 MHz, CDCl3) δ 8.42 (d, J = 0.9 Hz, 1H), 8.42 (d, J =0.7 Hz, 1H), 7.74 (s, 1H), 7.61 (d, J = 0.9 Hz, 1H), 7.61 (d, J = 0.7 Hz, 1H), 7.34 (s, 3H), 7.33-7.32 (m, 4H), 7.31 – 7.26 (m, 2H). 3.67 (s, 1H). 13 CNMR (100 MHz, CDCl3) δ 173.35, 150.43, 146.86, 144.17, 128.14, 128.11,127.62, 113.07, 79.79. Example 22

[0069] The product was prepared according to the preparation method of Example 19, except that p-cyanoaniline in the reaction was replaced with an equivalent amount of 3-aminopyrimidine, to obtain the final product 3v (0.294, 81%).

[0070] 3v: 1 H NMR (400 MHz, CDCl3) δ 8.93 (dd, J = 4.1, 1.7 Hz, 1H), 8.74 (t,J = 1.5 Hz, 1H), 8.63 (s, 1H), 7.47 (dd, J = 4.2, 1.5 Hz, 1H), 7.37-7.35 (m,3H), 7.34-7.31 (m, 4H), 7.30 – 7.26 (m, 2H). 3.71 (s, 1H) 13 C NMR (100 MHz, CDCl3) δ 174.48, 159.75, 157.14, 144.17, 128.14, 128.11, 127.62, 109.03,79.55. Example 23

[0071] The product was prepared according to the preparation method of Example 19, except that p-cyanoaniline in the reaction was replaced with an equivalent amount of aminoquinoline, and the final product 3w (0.276, 84%) was obtained.

[0072] 3w: 1H NMR (400 MHz, CDCl3) δ 8.67 (dd, J = 4.2, 1.8 Hz, 1H), 8.38 (d,J = 2.1 Hz, 1H), 7.93 (s, 1H), 7.91 (dd, J = 7.5, 1.8 Hz, 1H), 7.84 (dd, J =9.5, 2.2 Hz, 1H), 7.79 (d, J = 9.6 Hz, 1H), 7.48-7.29 (m, 8H), 7.31 – 7.26(m, 3H), 3.74 (s, 1H). 13 C NMR (100 MHz, CDCl3) δ 173.17, 148.55, 148.46,144.17, 139.34, 134.75, 128.14, 128.11, 127.81, 127.62, 118.82, 114.40,79.79. Example 24

[0073] The preparation was carried out according to the method described in Example 1, except that aniline was replaced with an equivalent amount of 2-aminobenzothiazole, aluminum chloride was replaced with an equivalent amount of Cu(OAc)2, the base reagent was replaced with an equivalent amount of potassium phosphate, and the solvent was replaced with NMP. The final product 3x (0.232, 80%) was obtained.

[0074] 3x: 1 H NMR (400 MHz, CDCl3) δ 7.87 (dd, J = 7.6, 1.4 Hz, 1H), 7.75 (dd,J = 7.3, 1.5 Hz, 1H), 7.72 (s, 1H), 7.55 (td, J = 8.0, 1.6 Hz, 1H), 7.46(ddd, J = 8.3, 7.3, 1.2 Hz, 1H), 7.35 – 7.31 (m, 6H), 7.30 – 7.26 (m, 2H).3.76 (s, 1H). 13 C NMR (100 MHz, CDCl3) δ 174.40, 162.21, 145.21, 144.17,131.11, 128.14, 128.11, 127.62, 127.01, 125.01, 121.91, 119.91, 78.69. Example 25

[0075] The product was prepared according to the preparation method of Example 1, except that the aniline in the reaction was replaced with an equivalent amount of N-methylaniline to obtain the final product 3y (0.352, 86%).

[0076] 3y: 1 H NMR (400 MHz, CDCl3) δ 8.67(s, 1H), 7.41 – 7.30 (m, 10H), 7.30 –7.25 (m, 2H), 7.17 – 7.12 (m, 2H), 7.10 (tt, J = 7.3, 1.4 Hz, 1H), 3.76 (s,1H).3.72 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ 171.39, 145.42, 144.04, 128.91,128.14, 128.11, 127.17, 120.13, 85.03, 40.10. Example 26

[0077] The preparation was carried out according to the method of Example 1, except that aniline in the reaction was replaced with an equivalent amount of N-phenylbenzamide, the base reagent was replaced with an equivalent amount of potassium hydroxide, and the solvent was replaced with NMP. The final product 3z (0.187.82%) was obtained.

[0078] 3z: 1 H NMR (400 MHz, CDCl3) δ 8.53(s, 1H), 7.84 – 7.80 (m, 2H), 7.63 –7.58 (m, 2H), 7.57 – 7.51 (m, 4H), 7.42 – 7.26 (m, 11H), 7.10 (tt, J = 7.3,1.5 Hz, 1H), 3.73 (s, 1H). 13 C NMR (100 MHz, CDCl3) δ 169.98, 167.52, 143.84,138.31, 135.45, 131.61, 129.25, 129.21, 128.81, 128.14, 128.11, 128.08,127.23, 127.17, 84.89. Example 27

[0079] The preparation was carried out according to the method of Example 1, except that aniline in the reaction was replaced with an equivalent amount of octylamine, and the base reagent was replaced with an equivalent amount of potassium carbonate. The final product 3aa (0.134, 80%) was obtained. 3aa: 1 H NMR (400 MHz, CDCl3) δ 8.34 (s, 1H), 7.33 (d, J = 4.5 Hz, 8H), 7.31 – 7.25 (m, 2H), 5.53 (t, J = 6.6 Hz, 1H), 3.18 (q, J = 6.2 Hz, 2H), 1.58– 1.48 (m, 2H), 1.31 – 1.24 (m, 10H), 0.92 – 0.86 (m, 3H). 13 C NMR (100 MHz, CDCl3) δ 175.24, 143.64, 128.14, 128.11, 127.62, 78.97, 41.81, 31.83, 29.35, 28.78, 28.22, 23.30, 22.67, 14.07. Example 28

[0080] The preparation was carried out according to the method of Example 1, except that aniline in the reaction was replaced with 10 equivalents of ammonia water, and the alkaline reagent was replaced with an equivalent amount of sodium bicarbonate. The final product 3ab (0.158, 80%) was obtained. 3ab: 1 H NMR (400 MHz, CDCl3) δ 7.41 – 7.39 (m, 3H), 7.35 – 7.31 (m,5H), 7.30 – 7.26 (m, 2H), 6.36 (s, 2H), 5.07 (s, 1H). 13 C NMR (100 MHz, CDCl3)δ 173.88, 143.99, 128.14, 128.11, 127.88, 77.57. Example 29

[0081] The preparation was carried out according to the method of Example 1, except that the diphenyl ethyl ketone in the reaction was replaced with an equivalent amount of o-tolyl-2-phenyl-ethane ketone, and the base reagent was replaced with an equivalent amount of sodium hydroxide. The final product 3ac (0.343.84%) was obtained.

[0082] 3ac:1 H NMR (400 MHz, CDCl3) δ 7.68 – 7.62 (m, 2H), 7.39 – 7.31 (m,5H), 7.31 – 7.25 (m, 4H), 7.23-7.18 (m, 2H), 7.15 (s, 1H), 6.93 (tt, J = 7.2,1.3 Hz, 1H), 3.68 (s, 1H), 2.32 (s, 3H). 13 C NMR (100 MHz, CDCl3) δ 173.54,143.95, 141.03, 140.29, 135.04, 131.89, 130.06, 128.64, 128.14, 128.11,128.01, 127.44, 126.66, 125.10, 120.27, 80.51, 21.07. Example 30

[0083] The product was prepared according to the preparation method of Example 29, except that o-tolyl-2-phenyl-ethane ketone in the reaction was replaced with an equivalent amount of m-tolyl-2-phenyl-ethane ketone, to obtain the final product 3ad (0.352, 87%).

[0084] 3ad: 1 H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.67 – 7.63 (m, 2H), 7.35– 7.32 (m, 6H), 7.31 – 7.25 (m, 2H), 7.21 (ddd, J = 7.5, 2.3, 1.2 Hz, 1H),7.13 (dt, J = 2.5, 1.3 Hz, 1H), 6.97 (ddt, J = 6.8, 2.0, 0.8 Hz, 1H), 6.93(tt, J = 7.1, 1.3 Hz, 1H), 3.68 (s, 1H), 2.35 (s, 3H). 13 C NMR (100 MHz, CDCl3)δ 173.17, 143.80, 143.47, 140.29, 137.92, 130.06, 128.14, 128.11, 128.09,127.62, 127.58, 127.32, 126.66, 125.09, 120.27, 79.65, 21.66. Example 31

[0085] The product was prepared according to the preparation method of Example 29, except that the o-tolyl-2-phenyl-ethane ketone in the reaction was replaced with an equivalent amount of p-tolyl-2-phenyl-ethane ketone, and the final product 3ae (0.349, 86%) was obtained.

[0086] 3ae: 1 H NMR (400 MHz, CDCl3) δ 8.23 ​​(s, 1H), 7.67 – 7.63 (m, 2H), 7.36– 7.31 (m, 6H), 7.28 (ddd, J = 8.8, 5.0, 3.7 Hz, 1H), 7.21 (d, J = 1.2 Hz,4H), 6.93 (tt, J = 7.2, 1.3 Hz, 1H), 3.68 (s, 1H), 2.40 (s, 3H). 13 C NMR (100MHz, CDCl3) δ 173.17, 143.80, 143.47, 140.29, 137.92, 130.06, 128.14, 128.11,128.09, 127.62, 127.58, 127.32, 126.66, 125.09, 120.27, 79.65, 21.66. Example 32

[0087] The product was prepared according to the preparation method of Example 31, except that the p-tolyl-2-phenyl-ethane ketone in the reaction was replaced with an equivalent amount of p-fluorophenyl-2-phenyl-ethane ketone, and the base reagent was replaced with an equivalent amount of potassium carbonate, to obtain the final product 3af (0.197, 81%).

[0088] 3af: 1 H NMR (400 MHz, CDCl3) δ 8.32 (s, 1H), 7.68 – 7.63 (m, 2H), 7.35– 7.30 (m, 8H), 7.30 – 7.26 (m, 1H), 7.21 – 7.17 (m, 2H), 6.93 (tt, J = 7.2,1.3 Hz, 1H), 3.66 (s, 1H). 13C NMR (100 MHz, CDCl3) δ 173.35, 162.31, 144.17,140.31, 140.29, 130.06, 129.49, 128.14, 128.11, 127.62, 126.66, 120.27,114.95, 80.01. Example 33

[0089] The preparation was carried out according to the preparation method of Example 31, except that the p-tolyl-2-phenyl-ethane ketone in the reaction was replaced with an equivalent amount of p-chlorophenyl-2-phenyl-ethane ketone, and the base reagent was replaced with an equivalent amount of potassium carbonate, to obtain the final product 3ag (0.271, 82%).

[0090] 3ag: 1 H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 7.67 – 7.63 (m, 2H), 7.35 – 7.31 (m, 6H), 7.31 – 7.29 (m, 2H), 7.28 (s, 1H), 7.27 – 7.26 (m, 2H), 6.93(tt, J = 7.2, 1.3 Hz, 1H), 3.67 (s, 1H). 13 C NMR (100 MHz, CDCl3) δ 173.35,144.17, 142.69, 140.29, 133.87, 130.06, 128.94, 128.37, 128.14, 128.11,127.62, 126.66, 120.27, 79.33. Example 34

[0091] The product was prepared according to the preparation method of Example 31, except that p-tolyl-2-phenyl-ethane ketone in the reaction was replaced with an equivalent amount of p-bromophenyl-2-phenyl-ethane ketone, and the base reagent was replaced with an equivalent amount of cesium carbonate, to obtain the final product 3ah (0.315, 80%).

[0092] 3ah: 1H NMR (400 MHz, CDCl3) δ 8.21 (s, 1H), 7.68 – 7.61 (m, 2H), 7.49– 7.44 (m, 2H), 7.36 – 7.31 (m, 6H), 7.30 – 7.25 (m, 3H), 6.93 (tt, J = 7.2,1.3 Hz, 1H), 3.71 (s, 1H). 13 C NMR (100 MHz, CDCl3) δ 173.35, 144.17, 143.46,140.29, 130.71, 130.06, 129.66, 128.14, 128.11, 127.62, 126.66, 122.31,120.27, 80.23. Example 35

[0093] The product was prepared according to the preparation method of Example 31, except that the p-tolyl-2-phenyl-ethane ketone in the reaction was replaced with an equivalent amount of p-trifluoromethylphenyl-2-phenyl-ethane ketone, and the base reagent was replaced with an equivalent amount of potassium hydroxide, to obtain the final product 3ai (0.271, 83%).

[0094] 3ai: 1 H NMR (400 MHz, CDCl3) δ 8.41 (s, 1H), 7.81 – 7.76 (m, 2H), 7.68– 7.63 (m, 2H), 7.53 – 7.47 (m, 2H), 7.36 – 7.31 (m, 6H), 7.28 (ddd, J = 8.8,5.0, 3.8 Hz, 1H), 6.93 (tt, J = 7.2, 1.3 Hz, 1H), 3.73 (s, 1H). 13 C NMR (100MHz, CDCl3) δ 173.35, 144.17, 143.56, 140.29, 130.28, 130.06, 128.14, 128.11,128.08, 127.62, 126.66, 125.40, 123.61, 120.27, 79.74. Example 36

[0095] The product was prepared according to the preparation method of Example 35, except that the p-trifluoromethylphenyl-2-phenyl-ethane ketone in the reaction was replaced with an equivalent amount of p-methylphenyl-2-tolyl-ethane ketone, and the final product 3aj (0.378, 84%) was obtained.

[0096] 3aj: 1 H NMR (400 MHz, CDCl3) δ 8.39 (s, 1H), 7.68 – 7.63 (m, 2H), 7.36– 7.31 (m, 2H), 7.21 (d, J = 1.2 Hz, 8H), 6.93 (tt, J = 7.2, 1.3 Hz, 1H),3.75 (s, 1H), 2.40 (s, 6H). 13 C NMR (100 MHz, CDCl3) δ 173.35, 141.49, 140.29, 138.02, 130.06, 128.73, 127.73, 126.66, 120.27, 79.67, 20.94. Example 37

[0097] The preparation was carried out according to the preparation method of Example 1, except that the diphenyl ethyl ketone in the reaction was replaced with an equivalent amount of p-hydroxyphenyl-2-phenyl-ethane ketone, and the base reagent was replaced with an equivalent amount of potassium bicarbonate, to obtain the final product 3ak (0.349,85%).

[0098] 3ak: 1 H NMR (400 MHz, CDCl3) δ 7.89 (s, 1H), 7.68 – 7.62 (m, 2H), 7.37– 7.31 (m, 6H), 7.28 (ddd, J = 8.8, 5.0, 3.8 Hz, 1H), 7.23 – 7.19 (m, 2H), 6.93 (tt, J = 7.2, 1.3 Hz, 1H), 6.90 – 6.84 (m, 2H). 3.68 (s, 1H). 13 C NMR (100MHz, CDCl3) δ 173.35, 157.29, 144.17, 140.29, 135.77, 130.06, 128.94, 128.14,128.11, 127.62, 126.66, 120.27, 115.18, 80.15. Example 38

[0099] The product was prepared according to the preparation method of Example 37, except that the p-hydroxyphenyl-2-phenyl-ethane ketone in the reaction was replaced with an equivalent amount of p-mercaptophenyl-2-phenyl-ethane ketone, and the final product 3al (0.387, 82%) was obtained.

[0100] 3al: 1 H NMR (400 MHz, CDCl3) δ 7.73 – 7.59 (m, 2H), 7.39 – 7.36 (m,2H), 7.35 – 7.31 (m, 6H), 7.28 (ddd, J = 8.8, 5.0, 3.8 Hz, 1H), 7.26 – 7.22(m, 2H), 6.93 (tt, J = 7.2, 1.3 Hz, 1H), 6.87 (s, 1H), 5.53 (s, 1H), 3.80 (s,1H). 13 C NMR (100 MHz, CDCl3) δ 173.35, 144.17, 141.71, 140.29, 130.96, 130.06,129.18, 128.25, 128.14, 128.11, 127.62, 126.66, 120.27, 79.95. Example 39

[0101] The preparation was carried out according to the preparation method of Example 37, except that the p-hydroxyphenyl-2-phenyl-ethane ketone in the reaction was replaced with an equivalent amount of p-methoxyphenyl-2-phenyl-ethane ketone, the base reagent was replaced with an equivalent amount of potassium hydroxide, and the solvent was replaced with NMP, to obtain the final product 3am (0.431, 88%).

[0102] 3am: 1 H NMR (400 MHz, CDCl3) δ 7.69 – 7.60 (m, 2H), 7.37 – 7.31 (m,6H), 7.28 (ddd, J = 8.8, 5.0, 3.7 Hz, 1H), 7.25 – 7.20 (m, 2H), 7.01 – 6.90 (m, 3H), 6.87 (s, 1H), 5.53 (s, 1H), 3.76 (s, 3H). 13C NMR (100 MHz, CDCl3) δ173.35, 159.35, 144.17, 140.29, 137.39, 130.06, 128.78, 128.14, 128.11,127.62, 126.66, 120.27, 113.18, 80.01, 55.32. Example 40

[0103] The preparation was carried out according to the preparation method of Example 1, except that the diphenyl ethyl ketone in the reaction was replaced with an equivalent amount of (2-naphthyl)-2-phenyl-ethane ketone, the base reagent was replaced with an equivalent amount of potassium phosphate, and the solvent was replaced with toluene, to obtain the final product 3an (0.383, 82%).

[0104] 3an: 1 H NMR (400 MHz, CDCl3) δ 8.02 – 7.98 (m, 1H), 7.90 (d, J = 8.0Hz, 1H), 7.85 – 7.81 (m, 1H), 7.80 (t, J = 1.9 Hz, 1H), 7.67 – 7.63 (m, 2H),7.55 – 7.50 (m, 2H), 7.42 (dd, J = 8.1, 1.8 Hz, 1H), 7.36 – 7.31 (m, 6H),7.28 (ddd, J = 8.8, 5.0, 3.8 Hz, 1H), 6.93 (tt, J = 7.2, 1.3 Hz, 1H), 6.87(s, 1H), 5.81 (s, 1H). 13 C NMR (100 MHz, CDCl3) δ 173.17, 143.80, 142.11,140.29, 133.75, 133.17, 130.06, 128.14, 128.11, 127.62, 127.19, 127.11,126.85, 126.66, 126.07, 125.94, 125.44, 124.18, 120.27, 79.17. Example 41

[0105] The preparation was carried out according to the preparation method of Example 1, except that the aniline in the reaction was replaced with an equivalent amount of 3,3-diphenylpropylamine, the base reagent was replaced with an equivalent amount of potassium hydroxide, and the solvent was replaced with DMA, to obtain the final product 3ao (0.437, 89%).

[0106] 3ao: 1 H NMR (400 MHz, CDCl3) δ 7.41-7.32 (m, 4H), 7.32-7.25 (m, 6H), 7.22 (t, J = 7.3 Hz, 4H), 7.13 (t, J = 8.0 Hz, 6H), 6.42 (s, 1H), 4.04 (s,1H), 3.77 (t, J = 7.8 Hz, 1H), 3.19 (dd, J = 13.1, 6.5 Hz, 2H), 2.22 (dd, J =14.4, 7.4 Hz, 2H). 13 C NMR (100 MHz, CDCl3) δ 173.12, 143.79, 142.85, 128.53,128.21, 127.96, 127.61, 127.45, 126.34, 81.26, 48.75, 38.62, 34.80. Test Example: Seed Germination and Growth Inhibition Activity Test 1. Seed pretreatment The selected seeds were disinfected with 1% sodium hypochlorite for 15 minutes, and then washed with sterile distilled water.

[0107] Two sheets of filter paper with a diameter of 9 cm were laid flat. 200 μL of DMF was pipetted into a beaker, one drop of Tween-80 emulsifier was added, followed by 9 mL of distilled water. Thirty treated seeds were placed in the petri dish and then placed in an artificial climate incubator. The seeds were initially cultured at a constant temperature under darkness for 3 days, then the conditions were adjusted to 12 hours of light and 12 hours of darkness per day, with the temperature (28 ℃) and humidity (75%) remaining unchanged, and cultured for another 5 days. As the culture time increased, the germination of the seeds was observed daily, and the number and germination rate of monocot and dicot seeds were recorded.

[0108] 2. Seed germination and growth activity test The test compound was prepared in three concentration gradients: 1 ppm, 10 ppm, and 100 ppm (prepared with DMF and diluted with sterile distilled water).

[0109] Two sheets of filter paper with a diameter of 9 cm were laid flat. Three concentration gradients of the prepared solution were transferred using a pipette, and 30 treated seeds were placed in each petri dish. The dishes were then placed in an artificial climate incubator. Initially, the seeds were incubated at a constant temperature under darkness for 3 days. Then, the conditions were adjusted to 12 hours of light and 12 hours of darkness per day, while maintaining the same temperature (28 ℃) and humidity (75%), for another 5 days. Each concentration was repeated five times. As the incubation period increased, the germination of the seeds was observed daily, and the number and germination rate of monocot and dicot seeds were recorded.

[0110] After the culture was completed, three plants were randomly selected from each petri dish, and the lengths of their roots and stems were measured and recorded. The average lengths of the roots and stems of the experimental group plants and the average lengths of the roots and stems of the control group plants were calculated, and the inhibition rate was calculated using the formula for calculating the inhibition rate.

[0111] Inhibition rate = [(average root or stem length of plants in the blank control group - average root or stem length of plants in the experimental group) ÷ (average root or stem length of plants in the blank control group)] × 100%.

[0112] If the inhibition rate value is >0, it indicates that the test compound inhibits plant growth; if the inhibition rate value is <0, it indicates that the test compound promotes plant growth.

[0113] The experimental results are shown in Table 1.

[0114] Table 1 Inhibition effect

[0115] The tested compounds inhibited seed germination, and this inhibition was positively correlated with concentration. In this test example, the compound prepared in Example 6 showed germination rates of 18%, 7%, 16%, and 12% for rapeseed, paddy field grass, barnyard grass, and sparse barnyard grass at 100 ppm, respectively, compared to 86% in the blank control group. Furthermore, the compound exhibited a significantly stronger inhibitory effect on the roots of these plants, with an inhibition rate as high as 92% on rapeseed roots. The compounds provided in the above examples are suitable for inhibiting seed germination and root and stem growth in barnyard grasses such as paddy field grass, barnyard grass, and sparse barnyard grass, and have great potential for weed control.

[0116] The preferred embodiments of the present invention have been described in detail above. However, the present invention is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the protection scope of the present invention.

[0117] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, the present invention will not describe the various possible combinations separately.

[0118] Furthermore, various different embodiments of the present invention can be combined in any way, as long as they do not violate the spirit of the present invention, they should also be regarded as the content disclosed by the present invention.

Claims

1. The application of an α-hydroxy-(α-diaryl)acetamide compound in the preparation of a drug for inhibiting seed germination activity and root and stem growth, characterized in that, Its structural formula is shown in equation (1): Equation (1) Among them, R and R1 are each independently selected from H, C1-C 20 The alkyl, aromatic, halogen, hydroxyl, mercapto, trifluoromethyl, nitro, ether, or thioether groups are selected independently from H, alkyl, aromatic, or heterocyclic groups.

2. The application according to claim 1, characterized in that, The minimum inhibitory concentration of the α-hydroxy-(α-diaryl)acetamide compounds is 1 ppm.

3. The method for preparing the α-hydroxy-(α-diaryl)acetamide compound according to claim 1, characterized in that, include: After dissolving diaryl ethyl ketone compounds and amino compounds in a solvent, an alkaline reagent and a catalyst are added, and the mixture is reacted at 150~180℃ for 20~24 h to obtain α-hydroxy-(α-diaryl)acetamide compounds.

4. The preparation method according to claim 3, characterized in that, The diaryl ethyl ketone compounds are selected from diphenyl ethyl ketone, o-tolyl-2-phenyl-ethane, m-tolyl-2-phenyl-ethane, p-tolyl-2-phenyl-ethane, p-fluorophenyl-2-phenyl-ethane, p-chlorophenyl-2-phenyl-ethane, p-bromophenyl-2-phenyl-ethane, p-trifluoromethylphenyl-2-phenyl-ethane, p-methylphenyl-2-tolyl-ethane, p-hydroxyphenyl-2-phenyl-ethane, p-mercaptophenyl-2-phenyl-ethane, p-methoxyphenyl-2-phenyl-ethane, and (2-naphthyl)-2-phenyl-ethane.

5. The preparation method according to claim 3, characterized in that, The amino compound is selected from aniline, benzylamine, o-methylaniline, m-methylaniline, p-methylaniline, trifluoromethoxyaniline, p-fluoroaniline, p-chloroaniline, p-bromoaniline, p-trifluoromethylaniline, m-trifluoromethylaniline, o-methylaniline, p-phenylaniline, naphthylamine, acetyleneaniline, cyclohexylamine, p-nitroaniline, methyl p-formate aniline, ethyl p-formate aniline, p-cyanoaniline, 4-aminopyridine, 3-aminopyrimidine, aminoquinoline, 2-aminobenzothiazole, N-methylaniline, N-phenylbenzamide, octylamine, ammonia, and 3,3-diphenylpropylamine.

6. The preparation method according to claim 3, characterized in that, The alkaline reagent is selected from one or more of cesium carbonate, potassium carbonate, potassium hydroxide, potassium tert-butoxide, potassium phosphate, potassium hydroxide, sodium bicarbonate, sodium hydroxide, and potassium bicarbonate.

7. The preparation method according to claim 3, characterized in that, The solvent is N,N-dimethylformamide, dimethylacetamide, toluene, or methylpyrrolidone.

8. The preparation method according to claim 3, characterized in that, The catalyst is selected from AlCl3, CuCl, AgCl, Ag2CO3, Ag2O, Cu(OTf)2, and Cu(OAc)2.

9. The preparation method according to claim 3, characterized in that, The molar ratio of the diaryl ethyl ketone compound, the amino compound, the base reagent, and the catalyst is 1:(1.1~1.3):(1.5~2):(0.02~0.03).

10. The preparation method according to any one of claims 3 to 9, characterized in that, After the reaction is complete, water is added first to quench the reaction system, then the pH value is adjusted to 5-6, and finally extraction, washing, drying and purification are performed to obtain pure α-hydroxy-(α-diaryl)acetamide compounds.

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