Pyrazole-quinoxaline derivative as well as preparation method and application thereof

Abstract

The invention belongs to the technical field of compound synthesis, and particularly relates to a pyrazol-quinoxaline derivative and a preparation method and application thereof.The pyrazol-quinoxaline derivative is based on combination of a pyrazol structure and quinoxaline ketone, scientific and reasonable connection is carried out by screening connecting bonds, connecting sites and the like, and the pyrazol-quinoxaline derivative is obtained. The pyrazole-quinoxaline weeding drug micromolecules with relatively stable physicochemical properties and excellent druggability are prepared; the derivative especially has a remarkable post-emergence inhibition effect on barnyard grass, eleusine indica, green bristlegrass, piemarker, amaranthus retroflexus and purslane.

Description

Technical Field

[0001] This invention belongs to the field of compound synthesis technology, specifically relating to a pyrazole-quinoxaline derivative, its preparation method, and its application. Background Technology

[0002] Weed growth has always been a major obstacle to crop growth. It competes with crops for nutrients, water, sunlight, space, and other essential resources, severely hindering the normal growth of various crops, leading to reduced yields and decreased quality of agricultural products. It also causes huge economic losses globally each year. Therefore, weed control is a key measure to ensure food production. Currently, chemical weeding is the main and important means of effectively controlling agricultural weeds. Therefore, developing new herbicides that are highly efficient, low in toxicity, broad-spectrum, and have low resistance risk has become an essential requirement for achieving sustainable agricultural production and further improving crop quality and yield.

[0003] 4-Hydroxyphenylpyruvate dioxygenase (HPPD) is an iron-dependent, non-heme oxygenase involved in tyrosine metabolism in most aerobic organisms. In the presence of oxygen, HPPD catalyzes the conversion of 4-hydroxyphenylpyruvate (HPPA) to homogentisic acid (HGA). In plants, homogentisic acid (HGA) is further converted to plastoquinone (PQ) and tocopherol, both important cofactors in the photosynthetic system. Inhibition of HPPD hinders the biosynthesis of plastoquinone (PQ) and tocopherol, leading to reduced carotenoid content and consequently affecting the plant's photosynthetic capacity. Weeds affected by HPPD inhibitors exhibit bleaching symptoms and die.

[0004] In recent years, small molecules containing quinoxaline fragments have been widely used in medicine, pesticides, and materials. Substituted quinoxalines possess a wealth of biological activities, such as anticancer, antimalarial, antiprotozoal, antifungal, antiviral, and herbicidal activity. These properties make quinoxaline a promising drug backbone. Currently, pyrazole compounds have become a focus of research in herbicide creation. Herbicides that have been developed and marketed, such as pyrazosulfuron, sulfosulfuron-methyl, pyrazosulfuron-methyl, benzosulfuron-methyl, and bensulfuron-methyl, all contain pyrazole structures. These herbicides have many advantages, including broad-spectrum weed control, environmental friendliness, low resistance risk, unique mechanisms of action, and high safety for subsequent crops, making them an important herbicide choice in modern agriculture. Therefore, designing and synthesizing small herbicides based on pyrazole units is highly consistent with current trends in new pesticide creation.

[0005] In the prior art, quinoxalinones are a class of nitrogen-containing compounds with fused heterocyclic structures. Due to their unique π-conjugated system and multi-site modification capabilities, they exhibit a wide range of biological activities in medicinal chemistry and pesticide chemistry, attracting significant attention from researchers. Existing studies have shown that quinoxalinone derivatives possess excellent antibacterial, antitumor, antiviral, insecticidal, and herbicidal activities. Especially in pesticide development, they hold great promise as core nuclei for designing novel, highly effective fungicides and herbicides. For example, patent CN110835321A discloses a triketone compound containing a quinoxaline structure, its preparation method, and its application; this compound exhibits highly efficient post-emergence herbicidal activity. Another example is patent CN115160238A, which discloses a quinoxaline phenoxyacetic acid ester compound, its preparation method, and its application; this compound exhibits good pre-emergence herbicidal activity and good safety in both rice and tobacco.

[0006] Therefore, combining quinoxalone with pyrazole structural units holds particular promise for obtaining a class of herbicidal compounds with novel structures, high crop safety, and broad-spectrum activity. Currently, no publicly available literature reports on quinoxalone-pyrazole compounds, nor have their systematic synthetic methods and herbicidal activity been reported. Summary of the Invention

[0007] To address the shortcomings of existing technologies, this invention proposes a pyrazole-quinoxaline derivative, its preparation method, and its application.

[0008] To achieve the above objectives, the technical solution adopted by the present invention is as follows: The first objective of this invention is to provide: a pyrazole-quinoxaline derivative, the general structural formula of which is as follows: 1. A pyrazole-quinoxaline derivative, the general structural formula of which is shown in formula (I): ; In formula (I): R 1 They are selected from H, CH3, halogens, and hydroxyl groups, respectively. R 2 The components are selected from H, O, C1-C6 alkyl, C1-C6 haloalkyl, Ar, and C1-C6 benzyl, respectively. R 3 and R 4 Each is independently selected from H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkyl-(C1-C3)alkylene, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, -R 7 -CO-R 8 ; R 5They are selected from H, C1-C6 alkyl, C1-C6 cycloalkyl, and C1-C6 haloalkyl, respectively; R 6 Selected from H, C1-C6 haloalkyl, C1-C6 alkoxy, (C1-C6)alkylsulfonyl, substituted or unsubstituted phenylsulfonyl, (C1-C4)alkylbenzoyl, substituted or unsubstituted benzoyl, 1-methylethyl ethyl carbonate, (ethoxycarbonyloxy)methyl, -SO2-Ar-R 9 -CONR 10 R 11 -CH2-CO-Ar-R 12 ; R 7 Selected from C1-C4 alkylene groups respectively; R 8 Selected from C1-C4 alkyl groups respectively; R 9 Selected from H, nitro, halogen, C1-C4 alkyl, C1-C4 alkoxy, and trifluoromethyl, respectively; R 10 and R 11 Each is independently selected from C1-C6 alkyl groups; R 12 The components are selected from H, halogen, hydroxyl, nitro, C1-C4 alkyl, C1-C4 alkoxy, and trifluoromethyl, respectively.

[0009] Ar refers to aryl groups, including phenyl groups; the dashed line indicates that the bond can be a double or single bond. In R... 6 The substitutions mentioned herein are alkyl or nitro substitutions.

[0010] Furthermore, the pyrazole-quinoxaline derivatives include the following compounds: Compound A1: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxaline-(1H)-one; Compound A2: 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxaline-2(1H)-one; Compound A3: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propylquinoxaline-2(1H)-one; Compound A4: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methylquinoxaline-2(1H)-one; Compound A5: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-3-methyl-1-(prop-2-yn-1-yl)quinoxaline-2(1H)-one; Compound A6: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-(2-oxopropyl)quinoxaline-2(1H)-one; Compound A7: 1-(cyclopropylmethyl)-7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-3-methylquinoxaline-2(1H)-one; Compound A8: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-phenylquinoxaline-2(1H)-one; Compound A9: 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-phenylquinoxaline-2(1H)-one; Compound A10: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-phenyl-1-propylquinoxaline-2(1H)-one; Compound A11: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-(trifluoromethyl)quinoxaline-2(1H)-one; Compound A12: 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(trifluoromethyl)quinoxaline-2(1H)-one; Compound A13: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-3-(trifluoromethyl)quinoxaline-2(1H)-one; Compound A14: 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxaline-2(1H)-one; Compound A15: 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazol-4-carbonyl)-1,3-dimethylquinoxaline-2(1H)-one; Compound A16: 4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate; Compound A17: ((4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)methyl ethyl carbonate; Compound A18: 1-((4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate; Compound A19: 7-(1,3-dimethyl-5-(2-(4-nitrophenyl)-2-oxoethoxy)-1H-pyrazol-4-carbonyl)-1-ethyl-3-methylquinoxalin-2(1H)-one; Compound A20: 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-methylquinoxaline-2(1H)-one; Compound A21: 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazol-4-carbonyl)-1-ethyl-3-methylquinoxalin-2(1H)-one; Compound A22: 4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate; Compound A23: 4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl diethylcarbamate; Compound A24: Ethyl 1-((4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate; Compound A25: 1-(cyclopropylmethyl)-7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazol-4-carbonyl)-3-methylquinoxalin-2(1H)-one; Compound A26: 4-(4-(cyclopropylmethyl)-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate; Compound A27: 1,3-dimethyl-4-(4-methyl-3-oxo-2-phenyl-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl-4-methylbenzenesulfonate; Compound A28: 1-((1,3-dimethyl-4-(4-methyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate; Compound A29: 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazol-4-carbonyl)-1-ethyl-3-phenylquinoxalin-2(1H)-one; Compound A30: 4-(4-ethyl-3-oxo-2-phenyl-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl-4-methylbenzenesulfonate; Compound A31: Ethyl 1-((4-(4-ethyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate; Compound A32: 1,3-dimethyl-4-(3-oxo-2-phenyl-4-propyl-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl-4-methylbenzenesulfonate; Compound A33: 1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl 4-methylbenzenesulfonate; Compound A34: 1,3-Dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazole-5-yldiethylcarbamate; Compound A35: ((1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl)oxy)methyl ethyl carbonate; Compound A36: 1-((1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate; Compound A37: 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-(trifluoromethyl)quinoxaline-2(1H)-one; Compound A38: 4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate; Compound A39: 4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yldiethylcarbamate; Compound A40: Ethyl 1-((4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate; Compound A41: 1,3-dimethyl-4-(3-oxo-4-propyl-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl-4-methylbenzenesulfonate; Compound A42: 1-((1,3-dimethyl-4-(3-oxo-4-propyl-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazole-5-yl)oxy)ethyl ethyl carbonate.

[0011] Compound A43: 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione; Compound A44: 6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione; Compound A45: 1,4-Diethyl-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,4-dihydroquinoxaline-2,3-dione; Compound A46: 1-((4-(1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1-methyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate; Compound A47: 1-((4-(1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate; Compound A48: 1-((4-(1,4-diethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1-methyl-1H-pyrazol-5-yl)oxy)ethyl carbonate.

[0012] A second objective of this invention is to provide a method for preparing the aforementioned pyrazole-quinoxaline derivatives, characterized by comprising the following steps: (1) Preparation of intermediate 1: Methyl 3,4-diaminobenzoate was dissolved in ethanol, and methyl 2-oxo-substituted methyl acetate was added. The reaction system was reacted at room temperature for 3 hours. After the reaction was completed, the solid was obtained by filtration, which is intermediate 1. The filtrate was concentrated under reduced pressure and filtered again to obtain a solid, and another portion of intermediate 1 was obtained.

[0013] (2) Preparation of intermediate 2: Intermediate 1 was dissolved in acetonitrile, cesium carbonate was slowly added, and the reaction was stirred continuously at room temperature for 0.5 hours. Then R was added. 2X (X: representing Cl, Br or I), slowly heat to 80℃, and reflux the reaction system for 1.5 hours; after the reaction is complete, cool the reaction solution to room temperature, filter, concentrate under reduced pressure, add 1 mol / L dilute hydrochloric acid to adjust the pH to 6-7, and then add ethyl acetate and water to the solution for extraction; separate the organic layer, wash with saturated brine, dry, concentrate, and obtain intermediate 2 by column chromatography; (3) Preparation of intermediate 3: Intermediate 2, lithium hydroxide monohydrate, and 80% methanol solution were mixed and stirred. The mixture was then heated to 50°C and stirred continuously for 2 hours. After the reaction was complete, the reaction solution was poured into ice water, and then dilute hydrochloric acid solution was added while stirring. When the pH of the mixture was adjusted to 2-3, a solid precipitated out. The solid was obtained by filtration and dried in a vacuum to obtain intermediate 3. (4) Preparation of intermediate 4: Intermediate 3, 2-chloro-1-methylpyridine iodide (CMPI), triethylamine, and dichloromethane were mixed and stirred for 1.5 hours. Then, 1,3-dimethyl-5-pyrazolone and triethylamine were added at room temperature, and the reaction system was allowed to react at room temperature for 8-12 hours. After the reaction was complete, dichloromethane and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine and saturated sodium bicarbonate solution, dried, concentrated, and subjected to column chromatography, drying, and column chromatography steps to obtain intermediate 4. (5) Preparation of intermediate 5: Take methyl 3,4-diaminobenzoate, dissolve it in 2 mol / L dilute hydrochloric acid, add oxalic acid, heat to 85℃, and stir continuously for 3 hours; after the reaction is completed, cool the reaction solution to room temperature, filter to obtain the solid, which is intermediate 5.

[0014] (6) Preparation of intermediate 6: Dissolve intermediate 5 in DMF, slowly add cesium carbonate, and stir continuously at room temperature for 0.5 hours. Then add R. 4 X (X: representing Cl, Br or I), slowly heat to 80℃ and reflux the reaction system for 1.5 hours; after the reaction is complete, cool the reaction solution to room temperature, add 1 mol / L dilute hydrochloric acid to adjust the pH to 6-7, and then add ethyl acetate and water to the solution for extraction; separate the organic layer, wash with saturated brine, dry, concentrate, and column chromatography to obtain intermediate 6; (7) Preparation of intermediate 7: Intermediate 6, lithium hydroxide monohydrate, and 80% methanol solution were mixed and stirred. The mixture was then heated to 50°C and stirred continuously for 1.5 hours. After the reaction was complete, the reaction solution was poured into ice water, and then dilute hydrochloric acid solution was added while stirring. When the pH of the mixture was adjusted to 2-3, a solid precipitated out. The solid was obtained by filtration and dried in a vacuum to obtain intermediate 7. (8) Preparation of intermediate 8: Intermediate 7, 2-chloro-1-methylpyridine iodide (CMPI), triethylamine, and dichloromethane were mixed and stirred for 1.5 hours. Then, 1,3-dimethyl-5-pyrazolone and triethylamine were added at room temperature, and the reaction system was allowed to react at room temperature for 8-12 hours. After the reaction was complete, dichloromethane and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain intermediate 8. (9) Preparation of pyrazole-quinoxaline derivatives of the target compound: Intermediate 4 or intermediate 8 is added to acetonitrile, followed by the addition of trimethylcyanosilane and triethylamine. The mixture is stirred and reacted at room temperature for 12-16 hours. After the reaction is complete, the system is concentrated under reduced pressure, and then dichloromethane and water are added to the solution for extraction. The organic layer is separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain a portion of pyrazole-quinoxaline derivatives. This portion of pyrazole-quinoxaline derivatives is added to acetonitrile, potassium carbonate is added, and the mixture is stirred continuously at room temperature for 0.5 hours. Then, R is added... 6 X (X: representing Cl or Br), slowly heat to 80℃, and reflux the reaction system for 1.5 hours; after the reaction is complete, cool the reaction solution to room temperature, concentrate the system under reduced pressure, and then extract with ethyl acetate and water; separate the organic layer, wash with saturated brine, dry, concentrate, and column chromatography to obtain another portion of pyrazole-quinoxaline derivatives; the R 6 X is any one of 2-bromo-1-(4-nitrophenyl)-1-ethyl ketone, 2-bromo-1-(p-tolyl)-1-ethyl ketone, chloromethyl ethyl carbonate, 1-chloroethyl ethyl carbonate, 2-bromo-1-phenyl-1-ethyl ketone, N,N-diethylcarbamoyl chloride, and 4-methylbenzenesulfonyl chloride.

[0015] In step (1), the amounts of methyl 3,4-diaminobenzoate and methyl 2-oxo-substituted methyl acetate are in a molar ratio of methyl 3,4-diaminobenzoate: methyl 2-oxo-substituted methyl acetate = 1:1.1; the amount of ethanol is controlled by adding 1 mL of ethanol per millimol of methyl 3,4-diaminobenzoate.

[0016] In step (2), the amounts of intermediate 1, cesium carbonate, and haloalkanes are calculated in the following molar ratio: intermediate 1: cesium carbonate, haloalkanes = 1:1.25:1.3; the amount of acetonitrile is controlled by adding 1 mL of acetonitrile per millimol of intermediate 1.

[0017] In step (3), the amount of intermediate 2 and lithium hydroxide monohydrate is calculated in molar ratio as follows: intermediate 2: lithium hydroxide monohydrate = 1:1.5; the amount of 80% methanol is controlled by adding 1 mL of 80% methanol per millimol of intermediate 2.

[0018] In step (4), the amounts of intermediate 3, CMPI, triethylamine, and 1,3-dimethyl-5-pyrazolone are calculated in the following molar ratio: intermediate 3: CMPI: triethylamine: 1,3-dimethyl-5-pyrazolone = 1:1.5:2.2:1.25; the amount of dichloromethane is controlled by adding 1 mL of dichloromethane per millimol of intermediate 3.

[0019] In step (5), the amounts of methyl 3,4-diaminobenzoate and oxalic acid are in a molar ratio of methyl 3,4-diaminobenzoate to oxalic acid = 1:1.2; the amount of 2 mol / L dilute hydrochloric acid is controlled by adding 1 mL of 2 mol / L dilute hydrochloric acid to every millimole of methyl 3,4-diaminobenzoate.

[0020] In step (6), the amounts of intermediate 5, cesium carbonate, and halohydrocarbon are in the following molar ratio: intermediate 5, cesium carbonate, halohydrocarbon = 1.0: 1.5: 2.0; the amount of acetonitrile is controlled by adding 1 mL of acetonitrile per millimol of intermediate 5.

[0021] In step (7), the amount of intermediate 6 and lithium hydroxide monohydrate used is calculated in the following molar ratio: intermediate 6: lithium hydroxide monohydrate = 1:1.5; the amount of 80% methanol used is controlled by adding 1 mL of 80% methanol per millimol of intermediate 6.

[0022] In step (8), the amounts of intermediate 7, CMPI, triethylamine, and 1,3-dimethyl-5-pyrazolone are in the following molar ratio: intermediate 7: CMPI: triethylamine: 1,3-dimethyl-5-pyrazolone = 1:1.5:2.2:1.25; the amount of dichloromethane is controlled by adding 1 mL of dichloromethane per millimol of intermediate 7.

[0023] In step (9), the amounts of intermediate 4, trimethylcyanosilane, and triethylamine are calculated in the following molar ratio: intermediate 4: trimethylcyanosilane: triethylamine = 1.0: 1.1: 1.5; the amount of acetonitrile is controlled by adding 1 mL of acetonitrile per millimol of intermediate 4.

[0024] In step (10), the amounts of compound A1–A13, potassium carbonate, and RX are in a molar ratio of 1:1.5:1.5; the amount of acetonitrile is controlled by adding 1 mL of acetonitrile per millimol of compound A1–A13.

[0025] In step (11), the amounts of intermediate 8, trimethylcyanosilane, and triethylamine are calculated in the following molar ratio: intermediate 8: trimethylcyanosilane: triethylamine = 1.0: 1.1: 1.5; the amount of acetonitrile is controlled by adding 1 mL of acetonitrile per millimol of intermediate 8.

[0026] In step (12), the amounts of compound A43–A45, potassium carbonate, and RX are in a molar ratio of 1:1.5:1.5; the amount of acetonitrile is controlled by adding 1 mL of acetonitrile per millimol of compound A43–A45.

[0027] The preparation route for the pyrazole-quinoxaline derivative is any one of the following: Route 1: Route 2: A third object of the present invention is to provide the use of the pyrazole-quinoxaline derivative in the preparation of herbicides or weed growth enzyme inhibitors.

[0028] Specifically, the weeds include goosegrass, barnyard grass, velvetleaf, amaranth retroflexus, purslane, foxtail grass, morning glory, zinnia, alfalfa, seed amaranth, crabgrass, clover, Sudan grass, arrowhead pea, Kentucky bluegrass, ryegrass, licorice, dandelion, bitter tongue grass, milkvetch, hairy vetch, marigold, rapeseed, shepherd's purse, beggar-ticks, and bermudagrass.

[0029] The beneficial effects of this invention are: This invention is based on the combination of pyrazole structure and quinoxaline, and through the screening of linkage bonds and linkage sites, a scientific and reasonable linkage is achieved to create a small molecule pyrazole-quinoxaline herbicide with relatively stable physicochemical properties and excellent drug-like properties. This derivative has a particularly significant post-emergence inhibitory effect on barnyard grass, goosegrass, foxtail grass, velvetleaf, amaranth, and purslane.

[0030] The results of post-emergence herbicidal activity tests showed that, at a dose of 300 g ai / ha, compounds A2, A9, A12, A16-A18, A21, A24, A30, A33, A35, A38, and A40 exhibited excellent herbicidal activity against barnyard grass, goosegrass, foxtail, velvetleaf, amaranth, and purslane, causing weed whitening and severely inhibiting their growth, with inhibition rates reaching 100%. At a dose of 75 g ai. / ha, compounds A18 and A24 both achieved 100% inhibition rates against barnyard grass, goosegrass, foxtail, velvetleaf, amaranth, and purslane, comparable to the positive controls mesotrione and benzoyl permethrin. At a dose of 18.75 g ai. / ha... At ai / ha dosage, compounds A18 and A24 exhibited herbicidal activity against velvetleaf, amaranth, and purslane comparable to that of mesotrione and benzoxazine.

[0031] The pyrazole-quinoxaline derivatives designed and synthesized in this invention have simple structures, simple preparation processes, low production costs, and high yields, and have great application prospects. Attached Figure Description

[0032] Figure 1 and Figure 2 The preparation routes for the pyrazole-quinoxaline derivatives in Examples 1-48 are shown. Detailed Implementation

[0033] Example 1: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxaline-(1H)-one (i.e., compound A1, C) 16 H 16 The preparation method of N4O3 includes the following steps: (1) Preparation of methyl 2-methyl-3-oxo-3,4-dihydroquinoxaline-6-carboxylic acid: 10.00 g (60.18 mmol) of methyl 3,4-diaminobenzoate was dissolved in 150 mL of ethanol, followed by the addition of 12.49 g (80.05 mmol) of methyl 2-oxo-methyl-acetic acid. The reaction mixture was allowed to react at room temperature for 3 hours. After the reaction was complete, the solid was obtained by filtration. The filtrate was concentrated under reduced pressure and filtered again to obtain 12.20 g of the solid intermediate, methyl 2-methyl-3-oxo-3,4-dihydroquinoxaloline-6-carboxylic acid, with a yield of 74.48%.

[0034] (2) Preparation of methyl 2,4-dimethyl-3-oxo-3,4-dihydroquinoxaline-6-carboxylic acid: 12.20 g (55.91 mmol) of methyl 2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carboxylate was dissolved in 200 mL of acetonitrile. Then, cesium carbonate (22.77 g, 69.89 mmol) was slowly added, and the reaction was allowed to proceed at room temperature for 0.5 hours. Iodomethane (10.32 g, 72.68 mmol) was then added, and the mixture was slowly heated to 80 °C and refluxed for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the solid was removed by filtration, and the system was concentrated under reduced pressure. Water was added to the system, and the pH was adjusted to 6-7 with 1 mol / L dilute hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 9.70 g of the intermediate methyl 2,4-dimethyl-3-oxo-3,4-dihydroquinoxalo-6-carboxylate, with a yield of 74.73%.

[0035] (3) Preparation of 2,4-dimethyl-3-oxo-3,4-dihydroquinoxaline-6-carboxylic acid: 9.70 g (41.77 mmol) of methyl 2,4-dimethyl-3-oxo-3,4-dihydroquinoxalo-6-carboxylic acid, 2.63 g (62.65 mmol) of lithium hydroxide monohydrate, and 100 mL of MeOH (80%) were mixed and stirred. The mixture was then heated to 50 °C and stirred continuously for 2 hours. After the reaction was complete, the reaction solution was poured into ice water, and then dilute hydrochloric acid solution was added with stirring. When the pH of the mixture was adjusted to 2-3, a solid precipitated out. After filtration and drying under vacuum, 7.11 g of the intermediate 2,4-dimethyl-3-oxo-3,4-dihydroquinoxalo-6-carboxylic acid was obtained, with a yield of 78.04%.

[0036] (4) Preparation of (2,4-dimethyl-3-oxo-3,4-dihydroquinoxaloline-6-carboxylic acid (1,3-dimethyl-1H-pyrazol-5-yl) ester: 2,4-Dimethyl-3-oxo-3,4-dihydroquinoxaloline-6-carboxylic acid (7.11 g, 32.58 mmol) was dissolved in dry dichloromethane, and then Et3N (3.63 g, 35.84 mmol) and CMPI (12.49 g, 48.87 mmol) were added. After stirring continuously for 1.5 hours, 1,3-dimethyl-5-pyrazolone (4.57 g, 40.73 mmol) and Et3N (3.63 g, 35.84 mmol) were added at room temperature, and the reaction system was allowed to react at room temperature for 8-12 hours. After the reaction was complete, dichloromethane and water were added to the solution for extraction; the organic layer was separated, washed with saturated brine and saturated sodium bicarbonate solution, dried, concentrated, and subjected to column chromatography to obtain 7.10 g of the intermediate (2,4-dimethyl-3-oxo-3,4-dihydroquinoxaloline-6-carboxylic acid (1,3-dimethyl-1H-pyrazol-5-yl) ester, yield 69.74%).

[0037] (5) Preparation of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxaline-(1H)-one (i.e., compound A1): (2,4-Dimethyl-3-oxo-3,4-dihydroquinoxaline-6-carboxylic acid (1,3-dimethyl-1H-pyrazol-5-yl) ester (7.10 g, 22.73 mmol) was mixed thoroughly with 150 ml of acetonitrile and stirred continuously for a period of time. Subsequently, trimethylcyanosilane (2.48 g, 25.01 mmol) and Et3N (3.45 g, 34.10 mmol) were added sequentially to the reaction system at room temperature, and the reaction was allowed to proceed for 12-16 hours at room temperature. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 2.0 g of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-1,3-dimethylquinoxaline-(1H)-one, with a yield of 28.16%. Example 2: 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxaline-2(1H)-one (i.e., compound A2, C) 17 H 18 The preparation method of N4O3 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 1-ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxaline-2(1H)-one (i.e., compound A2): 1,3-Dimethyl-1H-pyrazol-5-yl-4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxaline-6-carboxylic acid ester (5.60 g, 17.16 mmol) was mixed thoroughly with 120 mL of acetonitrile and stirred continuously for a period of time. Then, at room temperature, trimethylcyanosilane (1.87 g, 18.88 mmol) and Et3N (2.60 g, 25.74 mmol) were added sequentially to the reaction system, allowing it to react at room temperature for 12–16 hours. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 1.50 g of 1-ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-3-methylquinoxaline-2(1H)-one, with a yield of 26.78%. Example 3: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propylquinoxaline-2(1H)-one (i.e., compound A3, C) 18 H 20 The preparation method of N4O3 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propylquinoxalin-2(1H)-one (i.e., compound A3): 1,3-Dimethyl-1H-pyrazol-5-yl-4-propyl-2-methyl-3-oxo-3,4-dihydroquinoxaline-6-carboxylic acid ester (5.00 g, 14.69 mmol) was mixed thoroughly with 100 mL of acetonitrile and stirred continuously for a period of time. Then, at room temperature, trimethylcyanosilane (1.60 g, 16.16 mmol) and Et3N (2.23 g, 22.03 mmol) were added sequentially to the reaction system, allowing it to react at room temperature for 12–16 hours. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 1.47 g of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-3-methyl-1-propylquinoxaline-2(1H)-one, with a yield of 29.40%. Example 4: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methylquinoxaline-2(1H)-one (i.e., compound A4, C) 18 H 20 The preparation method of N4O3 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methylquinoxaline-2(1H)-one (i.e., compound A4): 1,3-Dimethyl-1H-pyrazol-5-yl-4-isopropyl-2-methyl-3-oxo-3,4-dihydroquinoxaline-6-carboxylic acid ester (4.32 g, 12.69 mmol) was mixed thoroughly with 70 mL of acetonitrile and stirred continuously for a period of time. Then, at room temperature, trimethylcyanosilane (1.39 g, 13.96 mmol) and Et3N (1.93 g, 19.04 mmol) were added sequentially to the reaction system, allowing it to react at room temperature for 12–16 hours. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 1.30 g of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-1-isopropyl-3-methylquinoxaline-2(1H)-one, with a yield of 30.09%. Example 5: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-(prop-2-yn-1-yl)quinoxaline-2(1H)-one (i.e., compound A5, C) 18 H 16 The preparation method of N4O3 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-(prop-2-yn-1-yl)quinoxaline-2(1H)-one (i.e., compound A5): 1,3-Dimethyl-1H-pyrazol-5-yl 4-(prop-2-yn-1-yl)-2-methyl-3-oxo-3,4-dihydroquinoxaline-6-carboxylic acid ester (7.30 g, 21.70 mmol) was mixed thoroughly with 120 mL of acetonitrile and stirred continuously for a period of time. Subsequently, trimethylcyanosilane (2.37 g, 23.87 mmol) and Et3N (3.29 g, 32.56 mmol) were added sequentially to the reaction system at room temperature, and the reaction was allowed to proceed for 12–16 hours at room temperature. After the reaction was complete, the system was concentrated under reduced pressure, and then dichloromethane and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 2.12 g of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-3-methyl-1-(prop-2-yn-1-yl)quinoxaline-2(1H)-one, with a yield of 29.04%. Example 6: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-(2-oxopropyl)quinoxaline-2(1H)-one (i.e., compound A6, C) 18 H 18 The preparation method of N4O4 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-(2-oxopropyl)quinoxaline-2(1H)-one (i.e., compound A6): 1,3-Dimethyl-1H-pyrazol-5-yl-4-(2-oxopropyl)-2-methyl-3-oxo-3,4-dihydroquinoxaline-6-carboxylic acid ester (6.80 g, 19.19 mmol) was mixed thoroughly with 120 mL of acetonitrile and stirred continuously for a period of time. Subsequently, trimethylcyanosilane (2.09 g, 21.11 mmol) and Et3N (2.91 g, 28.78 mmol) were added sequentially to the reaction system at room temperature, and the reaction was allowed to proceed for 12–16 hours at room temperature. After the reaction was complete, the system was concentrated under reduced pressure, and then dichloromethane and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 2.01 g of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-(2-oxopropyl)quinoxaline-2(1H)-one, with a yield of 29.55%. Example 7: 1-(cyclopropylmethyl)-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxaline-2(1H)-one (i.e., compound A7, C) 19 H 20 The preparation method of N4O3 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 1-(cyclopropylmethyl)-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxaline-2(1H)-one (i.e., compound A7): 1,3-Dimethyl-1H-pyrazol-5-yl-4-(cyclopropylmethyl)-2-methyl-3-oxo-3,4-dihydroquinoxaline-6-carboxylic acid ester (5.71 g, 16.20 mmol) was mixed thoroughly with 80 mL of acetonitrile and stirred continuously for a period of time. Then, at room temperature, trimethylcyanosilane (1.77 g, 17.82 mmol) and Et3N (2.46 g, 24.31 mmol) were added sequentially to the reaction system, allowing it to react at room temperature for 12–16 hours. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 1.89 g of 1-(cyclopropylmethyl)-7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-3-methylquinoxaline-2(1H)-one, with a yield of 33.09%. Example 8: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-phenylquinoxaline-2(1H)-one (i.e., compound A8, C) 21 H 18 The preparation method of N4O3 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-phenylquinoxalin-2(1H)-one (i.e., compound A8): 5.00 g (13.35 mmol) of 3-dimethyl-1H-pyrazol-5-yl-4-methyl-2-phenyl-3-oxo-3,4-dihydroquinoxaline-6-carboxylic acid ester was mixed thoroughly with 80 mL of acetonitrile and stirred continuously for a period of time. Then, at room temperature, trimethylcyanosilane (1.46 g, 14.69 mmol) and Et3N (2.03 g, 20.03 mmol) were added sequentially to the reaction system, and the reaction was allowed to proceed for 12-16 hours at room temperature. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 1.70 g of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-1-methyl-3-phenylquinoxaline-2(1H)-one, with a yield of 34.00%. Example 9: 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-phenylquinoxaline-2(1H)-one (i.e., compound A9, C) 22 H 20 The preparation method of N4O3 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 1-ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-phenylquinoxaline-2(1H)-one (i.e., compound A9): 1,3-Dimethyl-1H-pyrazol-5-yl-4-ethyl-2-phenyl-3-oxo-3,4-dihydroquinoxaline-6-carboxylic acid ester (4.97 g, 12.80 mmol) was mixed thoroughly with 80 mL of acetonitrile and stirred continuously for a period of time. Then, at room temperature, trimethylcyanosilane (1.40 g, 14.07 mmol) and Et3N (1.94 g, 19.19 mmol) were added sequentially to the reaction system, allowing it to react at room temperature for 12-16 hours. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 1.60 g of 1-ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-3-phenylquinoxaline-2(1H)-one, with a yield of 32.19%. Example 10: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-phenyl-1-propylquinoxalin-2(1H)-one (i.e., compound A10, C) 23 H 22 The preparation method of N4O3 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-phenyl-1-propylquinoxalin-2(1H)-one (i.e., compound A10): 1,3-Dimethyl-1H-pyrazol-5-yl-4-propyl-3-oxo-2-phenyl-3,4-dihydroquinoxaline-6-carboxylic acid ester (4.50 g, 11.18 mmol) was mixed thoroughly with 60 mL of acetonitrile and stirred continuously for a period of time. Then, at room temperature, trimethylcyanosilane (1.22 g, 12.30 mmol) and Et3N (1.70 g, 16.77 mmol) were added sequentially to the reaction system, allowing it to react at room temperature for 12-16 hours. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 1.56 g of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-3-phenyl-1-propylquinoxaline-2(1H)-one, with a yield of 34.66%. Example 11: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-(trifluoromethyl)quinoxaline-2(1H)-one (i.e., compound A11, C) 16 H 13 The preparation method of F3N4O3 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-(trifluoromethyl)quinoxaline-2(1H)-one (i.e., compound A11): 1,3-Dimethyl-1H-pyrazol-5-yl-4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carboxylic acid ester (5.72 g, 12.29 mmol) was mixed thoroughly with 80 mL of acetonitrile and stirred continuously for a period of time. Then, at room temperature, trimethylcyanosilane (1.34 g, 13.51 mmol) and Et3N (1.86 g, 18.43 mmol) were added sequentially to the reaction system, allowing it to react at room temperature for 12–16 hours. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 1.42 g of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-1-methyl-3-(trifluoromethyl)quinoxaline-2(1H)-one, with a yield of 24.82%. Example 12: 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(trifluoromethyl)quinoxaline-2(1H)-one (i.e., compound A12, C) 17 H 15 The preparation method of F3N4O3 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 1-ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(trifluoromethyl)quinoxaline-2(1H)-one (i.e., compound A12): 1,3-Dimethyl-1H-pyrazol-5-yl-4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carboxylic acid ester (6.00 g, 15.04 mmol) was mixed thoroughly with 80 mL of acetonitrile and stirred continuously for a period of time. Then, at room temperature, trimethylcyanosilane (1.72 g, 17.35 mmol) and Et3N (2.39 g, 23.66 mmol) were added sequentially to the reaction system, allowing it to react at room temperature for 12–16 hours. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 1.64 g of 1-ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-3-(trifluoromethyl)quinoxaline-2(1H)-one, with a yield of 27.33%. Example 13: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-3-(trifluoromethyl)quinoxaline-2(1H)-one (i.e., compound A13, C) 18 H 17 The preparation method of F3N4O3 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-3-(trifluoromethyl)quinoxaline-2(1H)-one (i.e., compound A13): 1,3-Dimethyl-1H-pyrazol-5-yl-4-propyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carboxylic acid ester (5.80 g, 14.71 mmol) was mixed thoroughly with 80 mL of acetonitrile and stirred continuously for a period of time. Then, at room temperature, trimethylcyanosilane (1.61 g, 16.18 mmol) and Et3N (2.23 g, 22.06 mmol) were added sequentially to the reaction system, allowing it to react at room temperature for 12–16 hours. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 1.70 g of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-1-propyl-3-(trifluoromethyl)quinoxaline-2(1H)-one, with a yield of 29.31%. Example 14: 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxaline-2(1H)-one (i.e., compound A14, C 24 H 22 The preparation method of N4O4 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxaline-2(1H)-one (i.e., compound A14): 20 mL of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxalin-(1H)-one (300 mg, 960.53 µmol) was dissolved in acetonitrile, and potassium carbonate (199.12 mg, 1.44 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 2-bromo-1-phenyl-1-ethylone (286.78 mg, 1.44 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction; the organic layer was separated, washed with saturated brine, dried, concentrated, and column chromatography was performed to obtain 0.35 g of 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxalin-2(1H)-one, with a yield of 82.92%; Example 15: A method for preparing 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxaline-2(1H)-one (i.e., compound A15), comprising the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxaline-2(1H)-one (i.e., compound A15, C 25 H 24 Preparation of N4O4: 20 mL of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxalin-(1H)-one (250 mg, 800.44 µmol) was dissolved in acetonitrile, and potassium carbonate (165.94 mg, 1.20 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 2-bromo-1-(p-tolyl)-1-ethyl ketone (255.83 mg, 1.20 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.29 g of 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxalin-2(1H)-one, with a yield of 82.92%. Example 16: 4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl 4-methylbenzenesulfonate (i.e., compound A16, C) 23 H 22 The preparation method of N4O5S includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl 4-methylbenzenesulfonate (i.e., compound A16): 20 mL of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxalin-(1H)-one (250 mg, 800.44 µmol) was dissolved in acetonitrile, and potassium carbonate (228.89 mg, 1.20 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 4-methylbenzenesulfonyl chloride (165.94 mg, 1.20 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.30 g of 4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate, with a yield of 81.08%. Example 17: ((4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)methyl ethyl carbonate (i.e., compound A17, C) 20 H 22 The preparation method of N4O6 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of ((4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)methyl ethyl carbonate (i.e., compound A17): 20 mL of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxalin-(1H)-one (250 mg, 800.44 µmol) was dissolved in acetonitrile, and potassium carbonate (165.94 mg, 1.20 mmol) was added. The mixture was stirred continuously at room temperature for 0.5 hours, and then chloromethyl ethyl carbonate (166.35 mg, 1.20 mmol) was added. The temperature was slowly increased to 80 °C, and the reaction system was allowed to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.25 g of ((4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)methylethyl carbonate, yield 75.75%. Example 18: 1-((4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A18, C) 21 H 24 The preparation method of N4O6 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1-((4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A18): 20 mL of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxalin-(1H)-one (250 mg, 800.44 µmol) was dissolved in acetonitrile, and potassium carbonate (165.94 mg, 1.20 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 1-chloroethyl ethyl carbonate (183.19 mg, 1.20 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.26 g of 1-((4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate, yield 76.02%. Example 19: A method for preparing 7-(1,3-dimethyl-5-(2-(4-nitrophenyl)-2-oxoethoxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-methylquinoxalin-2(1H)-one (i.e., compound A19), comprising the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) 7-(1,3-dimethyl-5-(2-(4-nitrophenyl)-2-oxoethoxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-methylquinoxalin-2(1H)-one (i.e., compound A19, C 25 H 23 Preparation of N5O6: 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxalin-2(1H)-one (300.00 mg, 919.24 µmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (190.57 mg, 1.38 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 2-bromo-1-(4-nitrophenyl)-1-ethyl one (336.50 mg, 1.38 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.36 g of 7-(1,3-dimethyl-5-(2-(4-nitrophenyl)-2-oxoethoxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-methylquinoxalin-2(1H)-one, with a yield of 80.00%. Example 20: 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-methylquinoxaline-2(1H)-one (i.e., compound A20, C) 25 H 24 The preparation method of N4O4 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-methylquinoxalin-2(1H)-one (i.e., compound A20): 20 mL of 1-ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxalin-2(1H)-one (250 mg, 766.03 µmol) was dissolved in acetonitrile, and potassium carbonate (158.80 mg, 1.15 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 2-bromo-1-phenyl-1-ethylone (228.72 mg, 1.15 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction; the organic layer was separated, washed with saturated brine, dried, concentrated, and column chromatography was performed to obtain 0.24 g of 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-methylquinoxalin-2(1H)-one, with a yield of 70.58%; Example 21: 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-methylquinoxalin-2(1H)-one (i.e., compound A21, C 26 H 26 The preparation method of N4O4 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-methylquinoxalin-2(1H)-one (i.e., compound A21): 20 mL of 1-ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxalin-2(1H)-one (250 mg, 766.03 µmol) was dissolved in acetonitrile, and potassium carbonate (158.80 mg, 1.15 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 2-bromo-1-(p-tolyl)-1-ethyl one (244.83 mg, 1.15 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.27 g of 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-methylquinoxalin-2(1H)-one, with a yield of 77.14%. Example 22: 4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate (i.e., compound A22, C) 24 H 24 The preparation method of N4O5S includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl 4-methylbenzenesulfonate (i.e., compound A22): 20 mL of 1-ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxalin-2(1H)-one (250 mg, 766.03 µmol) was dissolved in acetonitrile, and potassium carbonate (158.80 mg, 1.15 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 4-methylbenzenesulfonyl chloride (219.06 mg, 1.15 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.30 g of 4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate, with a yield of 81.08%. Example 23: 4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl diethylcarbamate (i.e., compound A23, C) 22 H 27 The preparation method of N5O4 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl diethylcarbamate (i.e., compound A23): 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxalin-2(1H)-one (300 mg, 919.24 µmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (190.57 mg, 1.38 mmol) was added. After stirring continuously at room temperature for 0.5 hours, N,N-diethylcarbamoyl chloride (186.96 mg, 1.38 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.28 g of 4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxaloline-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl diethylcarbamate, with a yield of 71.79%. Example 24: Ethyl 1-((4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate (i.e., compound A24, C) 22 H 26 The preparation method of N4O6 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of ethyl 1-((4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate (i.e., compound A24): 20 mL of 1-ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxalin-2(1H)-one (250 mg, 766.03 µmol) was dissolved in acetonitrile, and potassium carbonate (158.80 mg, 1.15 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 1-chloroethyl ethyl carbonate (175.32 mg, 1.15 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.22 g of ethyl 1-((4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate, with a yield of 64.70%. Example 25: 1-(cyclopropylmethyl)-7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazole-4-carbonyl)-3-methylquinoxalin-2(1H)-one (i.e., compound A25, C) 28 H 28 The preparation method of N4O4 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1-(cyclopropylmethyl)-7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazole-4-carbonyl)-3-methylquinoxalin-2(1H)-one (i.e., compound A25): Dissolve 20 mL of 1-(cyclopropylmethyl)-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxalin-2(1H)-one (300.00 mg, 851.32 µmol) in acetonitrile, add potassium carbonate (176.48 mg, 1.28 mmol), and stir continuously at room temperature for 0.5 hours. Then add 2-bromo-1-(p-tolyl)-1-ethylone (272.09 mg, 1.28 mmol), and slowly heat to 80 °C to allow the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.37 g of 1-(cyclopropylmethyl)-7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazol-4-carbonyl)-3-methylquinoxalin-2(1H)-one, with a yield of 89.80%. Example 26: 4-(4-(cyclopropylmethyl)-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl 4-methylbenzenesulfonate (i.e., compound A26, C) 26 H 26 The preparation method of N4O5S includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 4-(4-(cyclopropylmethyl)-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl 4-methylbenzenesulfonate (i.e., compound A26): 20 mL of 1-(cyclopropylmethyl)-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxalin-2(1H)-one (250.00 mg, 709.43 µmol) was dissolved in acetonitrile, and potassium carbonate (147.07 mg, 1.06 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 4-methylbenzenesulfonyl chloride (202.87 mg, 1.06 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.27 g of 4-(4-(cyclopropylmethyl)-2-methyl-3-oxo-3,4-dihydroquinoxaloline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate, with a yield of 75.00%. Example 27: 1,3-Dimethyl-4-(4-methyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl 4-methylbenzenesulfonate (i.e., compound A27, C) 28 H 24 The preparation method of N4O5S includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1,3-dimethyl-4-(4-methyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl 4-methylbenzenesulfonate (i.e., compound A27): 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-phenylquinoxalin-2(1H)-one (350.00 mg, 934.83 µmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (193.80 mg, 1.40 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 4-methylbenzenesulfonyl chloride (267.33 mg, 1.40 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.28 g of 1,3-dimethyl-4-(4-methyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl 4-methylbenzenesulfonate, with a yield of 57.14%. Example 28: 1-((1,3-dimethyl-4-(4-methyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A28, C) 26 H 26 The preparation method of N4O6 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1-((1,3-dimethyl-4-(4-methyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A28): 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-phenylquinoxalin-2(1H)-one (350.00 mg, 934.83 µmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (193.80 mg, 1.40 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 1-chloroethyl ethyl carbonate (213.95 mg, 1.40 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.29 g of 1,3-dimethyl-4-(4-methyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl 4-methylbenzenesulfonate, with a yield of 63.04%. Example 29: 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-phenylquinoxalin-2(1H)-one (i.e., compound A29, C) 31 H 28 The preparation method of N4O4 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-phenylquinoxalin-2(1H)-one (i.e., compound A29): 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-phenylquinoxalin-2(1H)-one (300.00 mg, 772.35 µmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (160.11 mg, 1.16 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 2-bromo-1-(p-tolyl)-1-ethylone (246.85 mg, 1.16 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction; the organic layer was separated, washed with saturated brine, dried, concentrated, and column chromatography was performed to obtain 0.24 g of 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-phenylquinoxalin-2(1H)-one, with a yield of 68.57%; Example 30: 4-(4-ethyl-3-oxo-2-phenyl-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl 4-methylbenzenesulfonate (i.e., compound A30, C) 29 H 26 The preparation method of N4O5S includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 4-(4-ethyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl 4-methylbenzenesulfonate (i.e., compound A30): 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-phenylquinoxalin-2(1H)-one (350.00 mg, 901.07 µmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (186.80 mg, 1.35 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 4-methylbenzenesulfonyl chloride (257.67 mg, 1.35 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.30 g of 4-(4-ethyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate, with a yield of 61.22%. Example 31: Ethyl 1-((4-(4-ethyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate (i.e., compound A31, C) 27 H 28 The preparation method of N4O6 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of ethyl 1-((4-(4-ethyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate (i.e., compound A31): 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-phenylquinoxalin-2(1H)-one (380.00 mg, 978.30 µmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (202.81 mg, 1.47 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 1-chloroethyl ethyl carbonate (223.90 mg, 1.47 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.31 g of ethyl 1-((4-(4-ethyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate, with a yield of 63.26%. Example 32: 1,3-Dimethyl-4-(3-oxo-2-phenyl-4-propyl-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl-4-methylbenzenesulfonate (i.e., compound A32, C 30 H 28 The preparation method of N4O5S includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1,3-dimethyl-4-(3-oxo-2-phenyl-4-propyl-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl-4-methylbenzenesulfonate (i.e., compound A32): 20 mL of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-phenyl-1-propylquinoxalin-2(1H)-one (350.00 mg, 869.66 µmol) was dissolved in acetonitrile, and potassium carbonate (180.29 mg, 1.30 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 4-methylbenzenesulfonyl chloride (248.69 mg, 1.30 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.32 g of 1,3-dimethyl-4-(3-oxo-2-phenyl-4-propyl-3,4-dihydroquinoxaloline-6-carbonyl)-1H-pyrazol-5-yl-4-methylbenzenesulfonate, with a yield of 66.66%. Example 33: 1,3-Dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl 4-methylbenzenesulfonate (i.e., compound A33, C 23 H 19 The preparation method of F3N4O5S includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl 4-methylbenzenesulfonate (i.e., compound A33): 20 mL of 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-(trifluoromethyl)quinoxalin-2(1H)-one (360.00 mg, 982.80 µmol) was dissolved in acetonitrile, and potassium carbonate (203.74 mg, 1.47 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 4-methylbenzenesulfonyl chloride (281.04 mg, 1.47 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.33 g of 1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl 4-methylbenzenesulfonate, with a yield of 64.56%. Example 34: 1,3-Dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazole-5-yl diethylcarbamate (i.e., compound A34, C 21 H 22 The preparation method of F3N5O4 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazole-5-yl diethylcarbamate (i.e., compound A34): 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-(trifluoromethyl)quinoxalin-2(1H)-one (380.00 mg, 1.04 mmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (215.06 mg, 1.56 mmol) was added. After stirring continuously at room temperature for 0.5 hours, N,N-diethylcarbamoyl chloride (210.99 mg, 1.56 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.38 g of 1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaloline-6-carbonyl)-1H-pyrazol-5-yl diethylcarbamate, with a yield of 79.17%. Example 35: A method for preparing ((1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl)oxy)methylethyl carbonate (i.e., compound A35), comprising the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) ((1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl)oxy)methyl ethyl carbonate (i.e., compound A35, C) 20 H 19 Preparation of F3N4O6: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-(trifluoromethyl)quinoxaline-2(1H)-one (380.00 mg, 1.04 mmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (215.06 mg, 1.56 mmol) was added. After stirring continuously at room temperature for 0.5 hours, chloromethyl ethyl carbonate (215.59 mg, 1.56 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.30 g of ((1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaloline-6-carbonyl)-1H-pyrazol-5-yl)oxy)methylethyl carbonate, yield 61.85%. Example 36: 1-((1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaloline-6-carbonyl)-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A36, C) 21 H 21 The preparation method of F3N4O6 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1-((1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaloline-6-carbonyl)-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A36): 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-(trifluoromethyl)quinoxaline-2(1H)-one (400.00 mg, 1.09 mmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (226.38 mg, 1.64 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 1-chloroethyl ethyl carbonate (249.92 mg, 1.64 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.34 g of 1-((1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaloline-6-carbonyl)-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate, with a yield of 64.64%. Example 37: 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-(trifluoromethyl)quinoxaline-2(1H)-one (i.e., compound A37, C) 25 H 21 The preparation method of F3N4O4 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-(trifluoromethyl)quinoxaline-2(1H)-one (i.e., compound A37): Dissolve 20 mL of 1-ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(trifluoromethyl)quinoxalin-2(1H)-one (250 mg, 657.33 µmol) in acetonitrile, add potassium carbonate (136.27 mg, 985.99 µmol), and stir continuously at room temperature for 0.5 hours. Then add 2-bromo-1-phenyl-1-ethylone (196.26 mg, 985.99 µmol), and slowly heat to 80 °C to allow the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction; the organic layer was separated, washed with saturated brine, dried, concentrated, and column chromatography was performed to obtain 0.24 g of 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-(trifluoromethyl)quinoxaline-2(1H)-one, with a yield of 73.39%; Example 38: 4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl 4-methylbenzenesulfonate (i.e., compound A38, C) 24 H 21 The preparation method of F3N4O5S includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl 4-methylbenzenesulfonate (i.e., compound A38): 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(trifluoromethyl)quinoxalin-2(1H)-one (360 mg, 936.55 µmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (196.23 mg, 1.42 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 4-methylbenzenesulfonyl chloride (270.68 mg, 1.42 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.35 g of 4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaloline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate, with a yield of 69.30%. Example 39: 4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl diethylcarbamate (i.e., compound A39, C) 22 H 24 The preparation method of F3N5O4 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl diethylcarbamate (i.e., compound A39): Dissolve 20 mL of 1-ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(trifluoromethyl)quinoxaline-2(1H)-one (380 mg, 999.14 µmol) in acetonitrile, add potassium carbonate (207.13 mg, 1.50 mmol), and stir continuously at room temperature for 0.5 hours. Then add N,N-diethylcarbamoyl chloride (203.21 mg, 1.50 mmol), and slowly heat to 80 °C to allow the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.32 g of 4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaloline-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl diethylcarbamate, with a yield of 66.80%. Example 40: Ethyl 1-((4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate (i.e., compound A40, C) 22 H 23 The preparation method of F3N4O6 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of ethyl 1-((4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate (i.e., compound A40): 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(trifluoromethyl)quinoxaline-2(1H)-one (400 mg, 1.05 mmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (218.03 mg, 1.58 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 1-chloroethyl ethyl carbonate (240.70 mg, 1.58 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.40 g of ethyl 1-((4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate, with a yield of 76.62%. Example 41: 1,3-Dimethyl-4-(3-oxo-4-propyl-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl-4-methylbenzenesulfonate (i.e., compound A41, C 25 H 23 The preparation method of F3N4O5S includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1,3-dimethyl-4-(3-oxo-4-propyl-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl-4-methylbenzenesulfonate (i.e., compound A41): 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-3-(trifluoromethyl)quinoxalin-2(1H)-one (360 mg, 912.88 µmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (189.25 mg, 1.37 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 4-methylbenzenesulfonyl chloride (261.05 mg, 1.37 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.36 g of 1,3-dimethyl-4-(3-oxo-4-propyl-2-(trifluoromethyl)-3,4-dihydroquinoxaloline-6-carbonyl)-1H-pyrazol-5-yl 4-methylbenzenesulfonate, with a yield of 72.00%. Example 42: 1-((1,3-dimethyl-4-(3-oxo-4-propyl-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A42, C) 23 H 25 The preparation method of F3N4O6 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1-((1,3-dimethyl-4-(3-oxo-4-propyl-2-(trifluoromethyl)-3,4-dihydroquinoxaloline-6-carbonyl)-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A42): 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-3-(trifluoromethyl)quinoxaline-2(1H)-one (400 mg, 1.01 mmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (210.27 mg, 1.52 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 1-chloroethyl ethyl carbonate (232.14 mg, 1.52 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.37 g of 1-((1,3-dimethyl-4-(3-oxo-4-propyl-2-(trifluoromethyl)-3,4-dihydroquinoxaloline-6-carbonyl)-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate, with a yield of 71.56%. Example 43: 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione (i.e., compound A43, C) 15 H 14 The preparation method of N4O4 includes the following steps: (1) Preparation of methyl 2,3-dioxo-1,2,3,4-tetrahydroquinoxalo-6-carboxylate: Methyl 3,4-diaminobenzoate (6.00 g, 36.11 mmol) was dissolved in 80 mL of dilute hydrochloric acid (2 mol / L), and oxalic acid (3.90 g, 43.33 mmol) was added. After stirring briefly, the mixture was heated to 85 °C and stirred continuously for 3 hours. After the reaction was completed, the reaction solution was cooled to room temperature and filtered to obtain a solid, namely 5.40 g of methyl 2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carboxylic acid, with a yield of 67.92%. (2) Preparation of methyl 1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carboxylic acid: 5.40 g (24.52 mmol) of methyl 2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carboxylate was dissolved in 80 mL of LDM. Cesium carbonate (11.99 g, 36.79 mmol) was slowly added, and the mixture was stirred continuously at room temperature for 0.5 hours. Then, methyl iodoform (6.96 g, 49.05 mmol) was added, and the mixture was slowly heated to 80 °C and refluxed for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, and the pH was adjusted to 6-7 with 1 mol / L dilute hydrochloric acid. Ethyl acetate and water were then added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 4.20 g of methyl 1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carboxylate, with a yield of 68.96%. (3) Preparation of 1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carboxylic acid: 4.20 g (16.92 mmol) of methyl 1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carboxylic acid, 1.06 g (23.38 mmol) of lithium hydroxide monohydrate, and 60 mL of MeOH (80%) were mixed and stirred. The mixture was then heated to 50 °C and stirred continuously for 2 hours. After the reaction was complete, the reaction solution was poured into ice water, and then dilute hydrochloric acid solution was added while stirring. When the pH of the mixture was adjusted to 2-3, a solid precipitated out. After filtration and drying under vacuum, 3.40 g of 1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carboxylic acid was obtained, with a yield of 85.85%.

[0038] (4) Preparation of 1-methyl-1H-pyrazole-5-yl-1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylic acid ester: Dissolve 4.20 g (14.52 mmol) of 1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carboxylic acid in 80 mL of dry dichloromethane. Then add Et3N (1.62 g (15.97 mmol) and CMPI (5.56 g (21.78 mmol) and stir continuously for 1.5 hours. Then add 1.78 g (18.15 mmol) of 2-methyl-2,4-dihydro-3H-pyrazol-3-one and Et3N (1.62 g (15.97 mmol)) at room temperature and allow the reaction system to react at room temperature for 8-12 hours. After the reaction was complete, dichloromethane and water were added to the solution for extraction; the organic layer was separated, washed with saturated brine and saturated sodium bicarbonate solution, dried, concentrated, and subjected to column chromatography to obtain 3.26 g of 1-methyl-1H-pyrazol-5-yl-1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carboxylic acid ester, with a yield of 71.49%. (5) Preparation of 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione (i.e., compound A43): 1-Methyl-1H-pyrazol-5-yl-1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylic acid ester (3.26 g, 10.37 mmol) was mixed thoroughly with 60 mL of acetonitrile and stirred continuously for a period of time. Then, at room temperature, trimethylcyanosilane (1.13 g, 11.41 mmol) and Et3N (1.57 g, 15.56 mmol) were added sequentially to the reaction system, allowing it to react at room temperature for 12–16 hours. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 1.12 g of 1-methyl-1H-pyrazol-5-yl-1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylic acid ester, with a yield of 34.35%. Example 44: 6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione (i.e., compound A44, C) 16 H 16 The preparation method of N4O4 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5) Preparation of 6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione (i.e., compound A44): 1,3-Dimethyl-1H-pyrazol-5-yl-1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carboxylic acid ester (3.50 g, 10.66 mmol) was mixed thoroughly with 60 mL of acetonitrile and stirred continuously for a period of time. Subsequently, trimethylcyanosilane (1.16 g, 11.73 mmol) and Et3N (1.62 g, 15.99 mmol) were added sequentially to the reaction system at room temperature, and the reaction was allowed to proceed at room temperature for 12–16 hours. After the reaction was complete, the system was concentrated under reduced pressure, and then dichloromethane and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 1.02 g of 6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione, with a yield of 29.14%. Example 45: 1,4-Diethyl-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,4-dihydroquinoxaline-2,3-dione (i.e., compound A45, C) 17 H 18 The preparation method of N4O4 includes the following steps: Steps (1)-(4): Refer to steps (1)-(4) of Example 1; (5): Preparation of 1,4-diethyl-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,4-dihydroquinoxaline-2,3-dione (i.e., compound A45): 1-Methyl-1H-pyrazol-5-yl-1,4-diethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylic acid ester (3.20 g, 9.35 mmol) was mixed thoroughly with 60 mL of acetonitrile and stirred continuously for a period of time. Then, at room temperature, trimethylcyanosilane (1.02 g, 10.28 mmol) and Et3N (1.42 g, 1402 mmol) were added sequentially to the reaction system, allowing it to react at room temperature for 12-16 hours. After the reaction was complete, the system was concentrated under reduced pressure, and then extracted with dichloromethane and water. The organic layer was separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain 0.96 g of 1,4-diethyl-6-(5-hydroxy-1-methyl-1H-pyrazol-4-carbonyl)-1,4-dihydroquinoxaline-2,3-dione, with a yield of 30.00%. Example 46: 1-((4-(1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1-methyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A46, C) 20 H 22 The preparation method of N4O7 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1-((4-(1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1-methyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A46): 20 mL of 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione (300 mg, 954.50 µmol) was dissolved in acetonitrile, and potassium carbonate (197.87 mg, 1.43 mmol) was added. The mixture was stirred continuously at room temperature for 0.5 hours, and then 1-chloroethyl ethyl carbonate (218.45 mg, 1.43 mmol) was added. The temperature was slowly increased to 80 °C, and the reaction system was allowed to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.30 g of 1-((4-(1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1-methyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate, with a yield of 73.5617%. Example 47: 1-((4-(1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A47, C) 21 H 24 The preparation method of N4O7 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1-((4-(1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A47): 6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione (400 mg, 1.22 mmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (252.56 mg, 1.83 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 1-chloroethyl ethyl carbonate (278.82 mg, 1.83 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.37 g of 1-((4-(1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate, with a yield of 68.51%. Example 48: 1-((4-(1,4-diethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1-methyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A48, C) 22 H 26 The preparation method of N4O7 includes the following steps: Steps (1)-(5): Refer to steps (1)-(5) of Example 1; (6) Preparation of 1-((4-(1,4-diethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1-methyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate (i.e., compound A48): 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione (350 mg, 1.02 mmol) was dissolved in 20 mL of acetonitrile, and potassium carbonate (211.94 mg, 1.53 mmol) was added. After stirring continuously at room temperature for 0.5 hours, 1-chloroethyl ethyl carbonate (233.97 mg, 1.53 mmol) was added, and the temperature was slowly raised to 80 °C, allowing the reaction system to react for 1.5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, the system was concentrated under reduced pressure, and then ethyl acetate and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 0.32 g of 1-((4-(1,4-diethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1-methyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate, with a yield of 68.08%. The structural and molecular formulas of the target compounds obtained in the above examples are shown in Table 1, and their physicochemical properties and spectral information are shown in Table 2. Table 1. Structural formulas of the target compounds obtained in Examples 1-48

[0039] Table 2. Spectral data of the target compounds obtained in Examples 1-48

[0040] Post-seeding activity test of target compound: This experiment used a spray method, with various weeds as test subjects. Weed seeds were evenly scattered in 8x8cm plastic pots filled two-thirds with organic substrate and grown in a greenhouse. The pots were used for testing when both grasses and broadleaf weeds reached the two- to three-leaf stage. 100... μ The compounds were dissolved in LDMF and diluted with 0.1% Tween-80 to a dose of 18.75–300 g ai / ha. Mesotrione and benzoxazine were used as positive controls and target compounds, respectively, to spray all weeds. After treatment, the weeds were left in a greenhouse for 21 days, and their herbicidal activity was evaluated visually in the control (CK) group, repeated three times.

[0041] Table 3 Post-emergence herbicidal activity of target compounds in Examples 1-48

[0042] Crop safety evaluation of the target compound: This experiment used a spray method, with various weeds as test subjects. Weed seeds were evenly scattered in 8x8cm plastic pots filled two-thirds with organic substrate and grown in a greenhouse. The pots were used for testing when both grasses and broadleaf weeds reached the two- to three-leaf stage. 100... μThe compound was dissolved in LDMF and diluted with 0.1% Tween-80 to a dose of 150 ga.i. / ha. Mesotrione and benzoxazine were used as positive controls and target compounds, respectively, to spray all weeds. After treatment, the weeds were left in a greenhouse for 21 days, and their herbicidal activity was evaluated visually in the control group (CK), repeated three times.

[0043] Table 4. Crop safety of the target compounds in Examples 18 and 24 at a dose of 150 g a.i. / ha.

[0044] As shown in Table 3, at a dose of 300 g a.i. / ha, compounds A2, A9, A12, A16–A18, A21, A24, A30, A33, A35, A38, and A40 exhibited excellent herbicidal activity against barnyard grass, goosegrass, foxtail, velvetleaf, amaranth, and purslane. The weeds showed obvious whitening symptoms, and their growth was severely inhibited, with inhibition rates reaching 10%. At a dose of 75 ga.i. / ha, compounds A18 and A24 showed 100% inhibition against barnyard grass, goosegrass, foxtail, velvetleaf, amaranth, and purslane, comparable to the positive controls mesotrione and benzoxazole; at a dose of 18.75 ga.i. / ha, the herbicidal activity of compounds A18 and A24 against velvetleaf, amaranth, and purslane was comparable to that of mesotrione and benzoxazole.

[0045] As shown in Table 4, compounds A18 and A24 exhibit superior crop safety compared to nicosulfuron and benzoxazine in crops such as rice, corn, wheat, peanut, soybean, and cotton. Among them, compounds A18 and A24 show a crop safety of no more than 20% in corn, rice, wheat, cotton, and peanut.

[0046] In summary, this series of pyrazole-quinoxaline derivatives exhibits excellent herbicidal and inhibitory activity. Therefore, this series of compounds can be used as novel post-emergence herbicides, and further development of novel selective herbicides will enable their application in more farmland.

[0047] The above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention in any way. Any simple modifications, equivalent changes, and alterations made to the above embodiments based on the technical essence of the present invention without departing from the scope of the present invention shall still fall within the scope of the present invention.

Claims

1. A pyrazole-quinoxaline derivative, characterized in that, The general structural formula of the derivative is as shown in formula (I): ； In formula (I): R 1 They are selected from H, CH3, halogens, and hydroxyl groups, respectively. R 2 The components are selected from H, O, C1-C6 alkyl, C1-C6 haloalkyl, Ar, and C1-C6 benzyl, respectively. R 3 and R 4 Each is independently selected from H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkyl-(C1-C3)alkylene, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, -R 7 -CO-R 8 ; R 5 They are selected from H, C1-C6 alkyl, C1-C6 cycloalkyl, and C1-C6 haloalkyl, respectively; R 6 Selected from H, C1-C6 haloalkyl, C1-C6 alkoxy, (C1-C6)alkylsulfonyl, substituted or unsubstituted phenylsulfonyl, (C1-C4)alkylbenzoyl, substituted or unsubstituted benzoyl, 1-methylethyl ethyl carbonate, (ethoxycarbonyloxy)methyl, -SO2-Ar-R 9 -CONR 10 R 11 -CH2-CO-Ar-R 12 ; R 7 Selected from C1-C4 alkylene groups respectively; R 8 Selected from C1-C4 alkyl groups respectively; R 9 Selected from H, nitro, halogen, C1-C4 alkyl, C1-C4 alkoxy, and trifluoromethyl, respectively; R 10 and R 11 Each is independently selected from C1-C6 alkyl groups; R 12 The components are selected from H, halogen, hydroxyl, nitro, C1-C4 alkyl, C1-C4 alkoxy, and trifluoromethyl, respectively. Ar refers to aryl groups, including phenyl groups; the dashed line indicates that the bond can be a double or single bond. In R... 6 The substitutions mentioned herein are alkyl or nitro substitutions.

2. The pyrazole-quinoxaline derivative as described in claim 1, characterized in that, Including the following compounds: Compound A1: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxaline-(1H)-one; Compound A2: 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methylquinoxaline-2(1H)-one; Compound A3: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propylquinoxaline-2(1H)-one; Compound A4: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methylquinoxaline-2(1H)-one; Compound A5: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-3-methyl-1-(prop-2-yn-1-yl)quinoxaline-2(1H)-one; Compound A6: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-(2-oxopropyl)quinoxaline-2(1H)-one; Compound A7: 1-(cyclopropylmethyl)-7-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-carbonyl)-3-methylquinoxaline-2(1H)-one; Compound A8: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-phenylquinoxaline-2(1H)-one; Compound A9: 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-phenylquinoxaline-2(1H)-one; Compound A10: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-phenyl-1-propylquinoxaline-2(1H)-one; Compound A11: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-methyl-3-(trifluoromethyl)quinoxaline-2(1H)-one; Compound A12: 1-Ethyl-7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(trifluoromethyl)quinoxaline-2(1H)-one; Compound A13: 7-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-3-(trifluoromethyl)quinoxaline-2(1H)-one; Compound A14: 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1,3-dimethylquinoxaline-2(1H)-one; Compound A15: 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazol-4-carbonyl)-1,3-dimethylquinoxaline-2(1H)-one; Compound A16: 4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate; Compound A17: ((4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)methyl ethyl carbonate; Compound A18: 1-((4-(2,4-dimethyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate; Compound A19: 7-(1,3-dimethyl-5-(2-(4-nitrophenyl)-2-oxoethoxy)-1H-pyrazol-4-carbonyl)-1-ethyl-3-methylquinoxalin-2(1H)-one; Compound A20: 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-methylquinoxaline-2(1H)-one; Compound A21: 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazol-4-carbonyl)-1-ethyl-3-methylquinoxalin-2(1H)-one; Compound A22: 4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate; Compound A23: 4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yl diethylcarbamate; Compound A24: Ethyl 1-((4-(4-ethyl-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate; Compound A25: 1-(cyclopropylmethyl)-7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazol-4-carbonyl)-3-methylquinoxalin-2(1H)-one; Compound A26: 4-(4-(cyclopropylmethyl)-2-methyl-3-oxo-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate; Compound A27: 1,3-dimethyl-4-(4-methyl-3-oxo-2-phenyl-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl-4-methylbenzenesulfonate; Compound A28: 1-((1,3-dimethyl-4-(4-methyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate; Compound A29: 7-(1,3-dimethyl-5-(2-oxo-2-(p-tolyl)ethoxy)-1H-pyrazol-4-carbonyl)-1-ethyl-3-phenylquinoxalin-2(1H)-one; Compound A30: 4-(4-ethyl-3-oxo-2-phenyl-3,4-dihydroquinoxaline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl-4-methylbenzenesulfonate; Compound A31: Ethyl 1-((4-(4-ethyl-3-oxo-2-phenyl-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate; Compound A32: 1,3-dimethyl-4-(3-oxo-2-phenyl-4-propyl-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl-4-methylbenzenesulfonate; Compound A33: 1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl 4-methylbenzenesulfonate; Compound A34: 1,3-Dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazole-5-yldiethylcarbamate; Compound A35: ((1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl)oxy)methyl ethyl carbonate; Compound A36: 1-((1,3-dimethyl-4-(4-methyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate; Compound A37: 7-(1,3-dimethyl-5-(2-oxo-2-phenethyloxy)-1H-pyrazole-4-carbonyl)-1-ethyl-3-(trifluoromethyl)quinoxaline-2(1H)-one; Compound A38: 4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl 4-methylbenzenesulfonate; Compound A39: 4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazole-5-yldiethylcarbamate; Compound A40: Ethyl 1-((4-(4-ethyl-3-oxo-2-(trifluoromethyl)-3,4-dihydroquinoxalo-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl carbonate; Compound A41: 1,3-dimethyl-4-(3-oxo-4-propyl-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazol-5-yl-4-methylbenzenesulfonate; Compound A42: 1-((1,3-dimethyl-4-(3-oxo-4-propyl-2-(trifluoromethyl)-3,4-dihydroquinoxaline-6-carbonyl)-1H-pyrazole-5-yl)oxy)ethyl ethyl carbonate. Compound A43: 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione; Compound A44: 6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,4-dimethyl-1,4-dihydroquinoxaline-2,3-dione; Compound A45: 1,4-Diethyl-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,4-dihydroquinoxaline-2,3-dione; Compound A46: 1-((4-(1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1-methyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate; Compound A47: 1-((4-(1,4-dimethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1,3-dimethyl-1H-pyrazol-5-yl)oxy)ethyl ethyl carbonate; Compound A48: 1-((4-(1,4-diethyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaloline-6-carbonyl)-1-methyl-1H-pyrazol-5-yl)oxy)ethyl carbonate.

3. The method for preparing the pyrazole-quinoxaline derivative as described in any one of claims 1-2, characterized in that, Includes the following steps: (1) Preparation of intermediate 1: Methyl 3,4-diaminobenzoate was dissolved in ethanol, and methyl 2-oxo-substituted methyl acetate was added. The reaction system was reacted at room temperature for 3 hours. After the reaction was completed, the solid was obtained by filtration, which is intermediate 1. The filtrate was concentrated under reduced pressure and filtered again to obtain a solid, and another portion of intermediate 1 was obtained. (2) Preparation of intermediate 2: Intermediate 1 was dissolved in acetonitrile, cesium carbonate was slowly added, and the reaction was stirred continuously at room temperature for 0.5 hours. Then R was added. 2 X (X: representing Cl, Br or I), slowly heat to 80℃, and reflux the reaction system for 1.5 hours; after the reaction is complete, cool the reaction solution to room temperature, filter, concentrate under reduced pressure, add 1 mol / L dilute hydrochloric acid to adjust the pH to 6-7, and then add ethyl acetate and water to the solution for extraction; separate the organic layer, wash with saturated brine, dry, concentrate, and obtain intermediate 2 by column chromatography; (3) Preparation of intermediate 3: Intermediate 2, lithium hydroxide monohydrate, and 80% methanol solution were mixed and stirred. The mixture was then heated to 50°C and stirred continuously for 2 hours. After the reaction was complete, the reaction solution was poured into ice water, and then dilute hydrochloric acid solution was added while stirring. When the pH of the mixture was adjusted to 2-3, a solid precipitated out. The solid was obtained by filtration and dried in a vacuum to obtain intermediate 3. (4) Preparation of intermediate 4: Intermediate 3, 2-chloro-1-methylpyridine iodide (CMPI), triethylamine, and dichloromethane were mixed and stirred for 1.5 hours. Then, 1,3-dimethyl-5-pyrazolone and triethylamine were added at room temperature, and the reaction system was allowed to react at room temperature for 8-12 hours. After the reaction was complete, dichloromethane and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine and saturated sodium bicarbonate solution, dried, concentrated, and subjected to column chromatography, drying, and column chromatography steps to obtain intermediate 4. (5) Preparation of intermediate 5: Take methyl 3,4-diaminobenzoate, dissolve it in 2 mol / L dilute hydrochloric acid, add oxalic acid, heat to 85℃, and stir continuously for 3 hours; after the reaction is completed, cool the reaction solution to room temperature, filter to obtain the solid, which is intermediate 5. (6) Preparation of intermediate 6: Dissolve intermediate 5 in DMF, slowly add cesium carbonate, and stir continuously at room temperature for 0.5 hours. Then add R. 4 X (X: representing Cl, Br or I), slowly heat to 80℃ and reflux the reaction system for 1.5 hours; after the reaction is complete, cool the reaction solution to room temperature, add 1 mol / L dilute hydrochloric acid to adjust the pH to 6-7, and then add ethyl acetate and water to the solution for extraction; separate the organic layer, wash with saturated brine, dry, concentrate, and column chromatography to obtain intermediate 6; (7) Preparation of intermediate 7: Intermediate 6, lithium hydroxide monohydrate, and 80% methanol solution were mixed and stirred. The mixture was then heated to 50°C and stirred continuously for 1.5 hours. After the reaction was complete, the reaction solution was poured into ice water, and then dilute hydrochloric acid solution was added while stirring. When the pH of the mixture was adjusted to 2-3, a solid precipitated out. The solid was obtained by filtration and dried in a vacuum to obtain intermediate 7. (8) Preparation of intermediate 8: Intermediate 7, 2-chloro-1-methylpyridine iodide (CMPI), triethylamine, and dichloromethane were mixed and stirred for 1.5 hours. Then, 1,3-dimethyl-5-pyrazolone and triethylamine were added at room temperature, and the reaction system was allowed to react at room temperature for 8-12 hours. After the reaction was complete, dichloromethane and water were added to the solution for extraction. The organic layer was separated, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain intermediate 8. (9) Preparation of pyrazole-quinoxaline derivatives of the target compound: Intermediate 4 or intermediate 8 is added to acetonitrile, followed by the addition of trimethylcyanosilane and triethylamine. The mixture is stirred and reacted at room temperature for 12-16 hours. After the reaction is complete, the system is concentrated under reduced pressure, and then dichloromethane and water are added to the solution for extraction. The organic layer is separated, washed with saturated brine, dried, concentrated, and purified by column chromatography to obtain a portion of pyrazole-quinoxaline derivatives. This portion of pyrazole-quinoxaline derivatives is added to acetonitrile, potassium carbonate is added, and the mixture is stirred continuously at room temperature for 0.5 hours. Then, R is added... 6 X (X: representing Cl or Br), slowly heat to 80℃, and reflux the reaction system for 1.5 hours; after the reaction is complete, cool the reaction solution to room temperature, concentrate the system under reduced pressure, and then extract with ethyl acetate and water; separate the organic layer, wash with saturated brine, dry, concentrate, and column chromatography to obtain another portion of pyrazole-quinoxaline derivatives; the R 6 X is any one of 2-bromo-1-(4-nitrophenyl)-1-ethyl ketone, 2-bromo-1-(p-tolyl)-1-ethyl ketone, chloromethyl ethyl carbonate, 2-bromo-1-phenyl-1-ethyl ketone, N,N-diethylcarbamoyl chloride, 4-methylbenzenesulfonyl chloride, and 1-chloroethyl ethyl carbonate.

4. The method for preparing the pyrazole-quinoxaline derivative as described in claim 3, characterized in that, In step (1), the molar ratio of methyl 3,4-diaminobenzoate and methyl 2-oxo-substituted methyl acetate is methyl 3,4-diaminobenzoate : methyl 2-oxo-substituted methyl acetate = 1 : 1.1; the amount of ethanol is controlled by adding 1 mL of ethanol per millimol of methyl 3,4-diaminobenzoate; in step (2), the molar ratio of intermediate 1, cesium carbonate, and haloalkanes is 1 : 1.25 : 1.3; the amount of acetonitrile is controlled by adding 1 mL of acetonitrile per millimol of intermediate 1; in step ( In step (3), the amount of intermediate 2 and lithium hydroxide monohydrate is calculated in the following molar ratio: intermediate 2: lithium hydroxide monohydrate = 1:1.5; the amount of 80% methanol is controlled by adding 1 mL of 80% methanol per millimol of intermediate 2; in step (4), the amount of intermediate 3, CMPI, triethylamine, and 1,3-dimethyl-5-pyrazolone is calculated in the following molar ratio: intermediate 3: CMPI: triethylamine: 1,3-dimethyl-5-pyrazolone = 1:1.5:2.2:1.25; the amount of dichloromethane is controlled by adding 1 mL of dichloromethane per millimol of intermediate 3.

5. The method for preparing the pyrazole-quinoxaline derivative as described in claim 3, characterized in that, In step (5), the molar ratio of methyl 3,4-diaminobenzoate to oxalic acid is methyl 3,4-diaminobenzoate: oxalic acid = 1:1.2; the amount of 2 mol / L dilute hydrochloric acid is controlled by adding 1 mL of 2 mol / L dilute hydrochloric acid per millimol of methyl 3,4-diaminobenzoate; in step (6), the molar ratio of intermediate 5, cesium carbonate, and haloalkanes is 1.0:1.5:2.0; the amount of acetonitrile is controlled by adding 1 mL of acetonitrile per millimol of intermediate 5; in step (7) The amounts of intermediate 6 and lithium hydroxide monohydrate are calculated in the following molar ratio: intermediate 6: lithium hydroxide monohydrate = 1:1.5; the amount of 80% methanol is controlled by adding 1 mL of 80% methanol per millimol of intermediate 6; in step (8), the amounts of intermediate 7, CMPI, triethylamine, and 1,3-dimethyl-5-pyrazolone are calculated in the following molar ratio: intermediate 7: CMPI: triethylamine: 1,3-dimethyl-5-pyrazolone = 1:1.5:2.2:1.25; the amount of dichloromethane is controlled by adding 1 mL of dichloromethane per millimol of intermediate 7.

6. The method for preparing the pyrazole-quinoxaline derivative as described in claim 3, characterized in that, In step (9), the amounts of intermediate 4, trimethylcyanosilane, and triethylamine are in the following molar ratio: intermediate 4: trimethylcyanosilane: triethylamine = 1.0: 1.1: 1.5; the amount of acetonitrile is controlled by adding 1 mL of acetonitrile per millimol of intermediate 4; in step (10), the compounds A1–A13, potassium carbonate, and R... 6 The dosage of X is calculated using a molar ratio of 1:1.5:1.5; the dosage of acetonitrile is controlled by adding 1 mL of acetonitrile per millimol of compound A1–A13.

7. The method for preparing the pyrazole-quinoxaline derivative as described in claim 3, characterized in that, In step (11), the amounts of intermediate 8, trimethylcyanosilane, and triethylamine are calculated in the following molar ratio: intermediate 8: trimethylcyanosilane: triethylamine = 1.0: 1.1: 1.5; the amount of acetonitrile is controlled by adding 1 mL of acetonitrile per millimol of intermediate 8; in step (12), the compounds A43–A45, potassium carbonate, and R... 6 The dosage of X is calculated as a molar ratio of 1:1.5:1.5; the dosage of acetonitrile is controlled by adding 1 mL of acetonitrile per millimol of compound A43–A45.

8. The use of the pyrazole-quinoxaline derivative as described in claim 1 in the preparation of herbicides or weed growth enzyme inhibitors.

9. The application as described in claim 8, characterized in that, The weeds mentioned are: goosegrass, barnyard grass, velvetleaf, reverse-branch amaranth, purslane, foxtail grass, morning glory, zinnia, alfalfa, seed amaranth, crabgrass, clover, Sudan grass, arrowhead pea, Kentucky bluegrass, ryegrass, licorice, dandelion, bitter tongue grass, milkvetch, hairy vetch, marigold, rapeseed, shepherd's purse, beggar-ticks, and bermudagrass.

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