Preparation method of pyroxasulfone metabolite M3
By using hydrogen peroxide and heteropolyacid catalysts to catalyze the oxidation of the pyrazole ring under alkaline conditions, the problems of low yield and serious pollution in the preparation of sulfonepyraclostrobin metabolite M3 were solved, and high-purity and high-yield preparation was achieved, simplifying the operation and meeting environmental protection requirements.
Patent Information
- Application Number
- CN202510576339.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-05-06
- Publication Date
- 2025-09-26
AI Technical Summary
The existing preparation method of sulfonepyraclostrobin metabolite M3 has the problems of low yield and serious pollution, especially the use of oxidants such as potassium permanganate to produce a large amount of manganese-containing high-salt wastewater, which is not conducive to environmental protection.
The invention adopts hydrogen peroxide combined with heteropolyacid catalyst to catalyze the oxidation of 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole under alkaline conditions, avoiding the use of highly polluting oxidants. The reaction efficiency and selectivity are improved by controlling the reaction conditions and the amount and time of catalyst addition.
The preparation of sulfonepyraclostrobin metabolite M3 with high yield (>91%) and high purity (>97wt%) was achieved, simplifying the operation and meeting green environmental protection requirements.
Smart Images
Figure HDA0005388692260000011
Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of pesticide synthesis, and in particular to a method for preparing a sulfonepyraclostrobin metabolite M3. Background Art
[0002] Pyroxasulfone, also known as rock-killing sulfone, is a new type of pyrazole selective herbicide. During the pesticide registration process, kilogram-level metabolite samples must be provided for toxicological testing. In the process of preparing metabolites, excessive oxidants such as potassium permanganate and chromate are generally used to oxidize primary alcohols into carboxylic acids. For example, Li Zhiyang et al. disclosed the synthesis of three major metabolites of pyroxasulfone (Synthetic Chemistry, 2024, 32(9)833-839). Using 1-methyl-3-trifluoromethyl-4-chloromethyl-5-difluoromethoxy-1-H-pyrazole as the raw material, the metabolites were prepared by potassium permanganate oxidation under alkaline conditions. This method not only produces a large amount of manganese-containing high-salt wastewater, is not conducive to environmental protection, but also has a low yield (82.5%). Summary of the Invention
[0003] In order to solve the above problems, the present invention provides a method for preparing the sulfonepyraclostrobin metabolite M3 with high yield, less three wastes and simple operation, which better meets the practical application needs.
[0004] The present invention provides a method for preparing a sulfonepyraclostrobin metabolite M3, which comprises at least the following steps: placing 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole and an alkaline aqueous solution in a reaction vessel, heating the reaction vessel to 70-90° C., adding a heteropolyacid catalyst and immediately dripping hydrogen peroxide; after the dripping is completed, the reaction is kept at 70-95° C. for 0.5-1 hour, and post-processing is performed to obtain the sulfonepyraclostrobin metabolite M3.
[0005] The invention uses 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole as a raw material, and catalytically oxidizes the primary alcohol of the pyrazole ring by using hydrogen peroxide in combination with a heteropolyacid catalyst under alkaline conditions, thereby avoiding the use of highly polluting oxidants such as potassium permanganate and chromic acid, and meeting the requirements of green environmental protection.
[0006] In one embodiment, the solute in the alkaline aqueous solution is at least one of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate.
[0007] In one embodiment, the solute in the alkaline aqueous solution is one of sodium hydroxide, potassium hydroxide or potassium carbonate.
[0008] In one embodiment, the concentration of the aqueous alkali solution is 3 to 25 wt%.
[0009] In one embodiment, the concentration of the aqueous alkali solution is 5 to 15 wt %.
[0010] In one embodiment, the heteropolyacid catalyst is selected from tetrakis (1-propyl-3-methylimidazolium) octamolybdate, tetrakis (1-propyl-3-methylimidazolium) decatungstate, tetrakis (1-hexadecyl-3-methylimidazolium) octamolybdate, tetrakis (1-hexadecyl-3-methylimidazolium) decatungstate, tetrakis (1-benzyl-3-methylimidazolium) octamolybdate, tetrakis (1-benzyl-3-methylimidazolium) decatungstate, tetrakis (hexadecyl-3-methylimidazolium) octamolybdate, tetrakis (1-benzyl-3-methylimidazolium) decatungstate, tetrakis (hexadecyl-3-methylimidazolium) octamolybdate, tetrakis (1-benzyl-3-methylimidazolium) decatungstate, At least one of tetra(1-butyl-3-methylpyridinium) octamolybdate, tetra(1-butyl-3-methylpyridinium) decatungstate, tetra(1-butyl-4-methylpyridinium) octamolybdate, tetra(1-butyl-4-methylpyridinium) decatungstate, tetra(1-ethylpyridinium) octamolybdate or tetra(1-ethylpyridinium) decatungstate and tetrabutylammonium decatungstate.
[0011] In one embodiment, the heteropolyacid catalyst is one of tetrakis(1-hexadecyl-3-methylimidazolium)octamolybdate, tetrabutylammonium decatungstate, or tetrakis(1-ethylpyridinium)octamolybdate.
[0012] In one embodiment, the molar ratio of the 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole, the aqueous base solution (based on the molar amount of the solute), and the hydrogen peroxide is 1: (0.9-2.5): (1-6).
[0013] In one embodiment, the molar ratio of the 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole, the aqueous base solution (based on the molar amount of the solute), and the hydrogen peroxide is 1: (1.0-2): (1.5-4).
[0014] In one embodiment, the molar ratio of the 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole, the aqueous base solution (based on the molar amount of the solute), and the hydrogen peroxide is 1: (1.01-1.2): (1.99-2.99).
[0015] In one embodiment, the mass ratio of the heteropolyacid catalyst to 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole is 1:(10-60).
[0016] In one embodiment, the mass ratio of the heteropolyacid catalyst to 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole is 1:(20-40).
[0017] In one embodiment, the time for adding the heteropolyacid catalyst dropwise is 1.5-2.5 hours.
[0018] In one embodiment, the concentration of the hydrogen peroxide is 20-40 wt %.
[0019] In one embodiment, the concentration of the hydrogen peroxide is 30 wt %.
[0020] Furthermore, the present invention ensures catalytic reaction efficiency and improves product purity and yield by comprehensively controlling the molar ratio of 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole, aqueous alkali solution, and hydrogen peroxide in the system, as well as the reaction conditions. In particular, the present invention utilizes one of tetrakis(1-hexadecyl-3-methylimidazolium) octamolybdate, tetrabutylammonium decatungstate, or tetrakis(1-ethylpyridinium) octamolybdate as the catalyst, and further controls the amount and addition time of the heteropolyacid catalyst to ensure reaction selectivity, resulting in a product with a purity greater than 97% by weight and a yield greater than 91%.
[0021] In one embodiment, the post-treatment comprises the following steps: filtering to remove the catalyst, adding concentrated hydrochloric acid to acidify to pH = 1-2, filtering, rinsing, and drying to obtain the sulfonepyraclostrobin metabolite M3.
[0022] The preparation method provided by the invention is simple to operate and easy to control, can meet kilogram-level experimental requirements, and has high practical value.
[0023] Beneficial effects
[0024] 1. The present invention provides a method for preparing the sulfonepyraclostrobin metabolite M3 with high yield, less three wastes and simple operation, which better meets the practical application needs.
[0025] 2. The present invention uses 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole as a raw material, and catalytically oxidizes the primary alcohol of the pyrazole ring by hydrogen peroxide combined with a heteropolyacid catalyst under alkaline conditions, avoiding the use of highly polluting oxidants such as potassium permanganate and chromic acid, thereby meeting the requirements of green environmental protection.
[0026] 3. The present invention ensures the catalytic reaction efficiency and improves the product purity and yield by comprehensively controlling the molar ratio of 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole, aqueous alkali solution, and hydrogen peroxide and the reaction conditions in the system.
[0027] 4. The present invention uses one of tetrakis(1-hexadecyl-3-methylimidazolium) octamolybdate, tetrabutylammonium decatungstate, or tetrakis(1-ethylpyridinium) octamolybdate as a catalyst, further controlling the amount of the heteropolyacid catalyst added and the addition time to ensure the reaction selectivity, so that the purity of the obtained product is greater than 97wt% and the yield is greater than 91%.
[0028] 5. The preparation method provided by the present invention is simple to operate, easy to control, can meet the requirements of kilogram-level experiments, and has high practical value. BRIEF DESCRIPTION OF THE DRAWINGS
[0029] Figure 1 The sulfone metabolite M3 prepared in Example 1 1 H NMR spectrum. DETAILED DESCRIPTION
[0030] Except for the commercially available tetrabutylammonium decatungstate, the heteropolyacid catalysts used in the present invention were prepared by referring to the method disclosed in Green Chem, 2016, 18, 2133.
[0031] Example 1
[0032] Example 1 of the present invention provides a method for preparing a sulfonepyraclostrobin metabolite M3, comprising the following steps: placing 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole (200 g, 0.8 mmol, 1 eq.) and an alkaline aqueous solution (649.78 g, 0.81 mol, 1.02 eq.) in a reaction vessel, heating the vessel to 70° C., adding a heteropolyacid catalyst (10 g) and immediately adding dropwise hydrogen peroxide (180.5 g, 1.59 mol, 2 eq.); after the addition is completed, the mixture is kept warm at 70° C. for 0.5 h, and the sulfonepyraclostrobin metabolite M3 (197.12 g, content 98.25 wt%, yield 93.5%) is obtained through post-treatment.
[0033] The alkaline aqueous solution is a 5 wt % sodium hydroxide aqueous solution.
[0034] The heteropolyacid catalyst is tetrakis(1-hexadecyl-3-methylimidazolium)octamolybdate.
[0035] The time for adding the heteropolyacid catalyst dropwise is 2 hours.
[0036] The concentration of the hydrogen peroxide solution is 30 wt %.
[0037] The post-treatment comprises the following steps: filtering to remove the catalyst, adding concentrated hydrochloric acid (37 wt %) to acidify to pH=1.5, filtering, rinsing and drying to obtain the sulfonepyraclostrobin metabolite M3.
[0038] Example 2
[0039] Example 2 of the present invention provides a method for preparing a sulfonepyraclostrobin metabolite M3, comprising the following steps: placing 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole (200 g, 0.8 mmol, 1 eq.) and an alkaline aqueous solution (807.08 g, 0.88 mol, 1.1 eq.) in a reaction vessel, heating to 80° C., adding a heteropolyacid catalyst (6.7 g) and immediately adding dropwise hydrogen peroxide (180.5 g, 1.59 mol, 2 eq.); after the addition is completed, the mixture is kept warm at 80° C. for 1 h, and the sulfonepyraclostrobin metabolite M3 (197.91 g, content 97.44 wt%, yield 93.1%) is obtained through post-treatment.
[0040] The alkaline aqueous solution is a 15 wt% potassium carbonate aqueous solution.
[0041] The heteropolyacid catalyst is tetrakis(1-hexadecyl-3-methylimidazolium)octamolybdate.
[0042] The time for adding the heteropolyacid catalyst dropwise is 2 hours.
[0043] The concentration of the hydrogen peroxide solution is 30 wt %.
[0044] The post-treatment comprises the following steps: filtering to remove the catalyst, adding concentrated hydrochloric acid (37 wt %) to acidify to pH=1.5, filtering, rinsing and drying to obtain the sulfonepyraclostrobin metabolite M3.
[0045] Example 3
[0046] Example 3 of the present invention provides a method for preparing a sulfonepyraclostrobin metabolite M3, comprising the following steps: placing 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole (200 g, 0.8 mmol, 1 eq.) and an alkaline aqueous solution (982.96 g, 0.88 mol, 1.1 eq.) in a reaction vessel, heating to 80° C., adding a heteropolyacid catalyst (5 g) and immediately adding dropwise hydrogen peroxide (225.62 g, 1.99 mol, 2.5 eq.); after the addition is completed, the mixture is kept warm at 85° C. for 0.5 h, and the sulfonepyraclostrobin metabolite M3 (194.56 g, content 98.69%, yield 92.7%) is obtained through post-treatment.
[0047] The alkaline aqueous solution is a 5% potassium hydroxide aqueous solution.
[0048] The heteropolyacid catalyst is tetrabutylammonium decatungstate.
[0049] The time for adding the heteropolyacid catalyst dropwise is 2.5 hours.
[0050] The concentration of the hydrogen peroxide solution is 30 wt %.
[0051] The post-treatment comprises the following steps: filtering to remove the catalyst, adding concentrated hydrochloric acid (37 wt %) to acidify to pH=1.5, filtering, rinsing and drying to obtain the sulfonepyraclostrobin metabolite M3.
[0052] Example 4
[0053] Example 4 of the present invention provides a method for preparing a sulfonepyraclostrobin metabolite M3, comprising the following steps: placing 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole (200 g, 0.8 mmol, 1 eq.) and an alkaline aqueous solution (880.45 g, 0.96 mol, 1.2 eq.) in a reaction vessel, heating the vessel to 90° C., adding a heteropolyacid catalyst (5 g) and immediately adding dropwise hydrogen peroxide (270.74 g, 2.39 mol, 3 eq.); after the addition is completed, the mixture is kept warm at 90° C. for 1 minute, and the sulfonepyraclostrobin metabolite M3 (195.8 g, content 97.96 wt%, yield 92.6%) is obtained through post-treatment.
[0054] The alkaline aqueous solution is a 15 wt% potassium carbonate aqueous solution.
[0055] The heteropolyacid catalyst is tetrakis(1-hexadecyl-3-methylimidazolium)octamolybdate.
[0056] The time for adding the heteropolyacid catalyst dropwise is 1.5 hours.
[0057] The concentration of the hydrogen peroxide solution is 30 wt %.
[0058] The post-treatment comprises the following steps: filtering to remove the catalyst, adding concentrated hydrochloric acid (37 wt %) to acidify to pH=1.5, filtering, rinsing and drying to obtain the sulfonepyraclostrobin metabolite M3.
[0059] Example 5
[0060] Example 5 of the present invention provides a method for preparing a sulfonepyraclostrobin metabolite M3, comprising the following steps: placing 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole (200 g, 0.8 mmol, 1 eq.) and an alkaline aqueous solution (536.16 g, 0.96 mol, 1.2 eq.) in a reaction vessel, heating to 90° C., adding a heteropolyacid catalyst (6.67 g) and immediately adding dropwise hydrogen peroxide (270.74 g, 2.39 mol, 3 eq.); after the addition is completed, the mixture is kept warm at 95° C. for 0.5 h, and the sulfonepyraclostrobin metabolite M3 (201.29 g, content 97.55%, yield 94.8%) is obtained through post-treatment.
[0061] The alkaline aqueous solution is a 10 wt % potassium hydroxide aqueous solution.
[0062] The heteropolyacid catalyst is tetrakis(1-ethylpyridinium)octamolybdate.
[0063] The time for adding the heteropolyacid catalyst dropwise is 2 hours.
[0064] The concentration of the hydrogen peroxide solution is 30 wt %.
[0065] The post-treatment comprises the following steps: filtering to remove the catalyst, adding concentrated hydrochloric acid (37 wt %) to acidify to pH=1.5, filtering, rinsing and drying to obtain the sulfonepyraclostrobin metabolite M3.
[0066] Example 6
[0067] Example 6 of the present invention provides a method for preparing a sulfonepyraclostrobin metabolite M3, comprising the following steps: placing 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole (200 g, 0.8 mmol, 1 eq.) and an alkaline aqueous solution (649.78 g, 0.81 mol, 1.02 eq.) in a reaction vessel, heating to 70° C., adding a heteropolyacid catalyst (10 g) and immediately adding dropwise hydrogen peroxide (225.62 g, 1.99 mol, 2.5 eq.); after the addition is completed, the mixture is kept warm at 70° C. for 0.5 h, and the sulfonepyraclostrobin metabolite M3 (192.85 g, content 98.17 wt%, yield 91.4%) is obtained through post-treatment.
[0068] The alkaline aqueous solution is a 5 wt % sodium hydroxide aqueous solution.
[0069] The heteropolyacid catalyst is tetrakis(1-ethylpyridinium)octamolybdate.
[0070] The time for adding the heteropolyacid catalyst dropwise is 2.5 hours.
[0071] The concentration of the hydrogen peroxide solution is 30 wt %.
[0072] The post-treatment comprises the following steps: filtering to remove the catalyst, adding concentrated hydrochloric acid (37 wt %) to acidify to pH=1.5, filtering, rinsing and drying to obtain the sulfonepyraclostrobin metabolite M3.
[0073] Comparative Example 1
[0074] Comparative Example 1 of the present invention provides a method for preparing a sulfonepyraclostrobin metabolite M3, comprising the following steps: placing 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole (200 g, 0.8 mmol, 1 eq.) and an alkaline aqueous solution (268.08 g, 1.19 mol, 1.5 eq.) in a reaction vessel, heating to 40° C., adding a heteropolyacid catalyst (40 g) and immediately adding dropwise hydrogen peroxide (135.37 g, 1.19 mol, 1.5 eq.); after the addition is completed, the mixture is kept warm at 45° C. for 0.5 h, and post-processed to obtain a sulfonepyraclostrobin metabolite M3 (160.68 g, content 94.36 wt%, yield 73.2%).
[0075] The alkaline aqueous solution is a 25% potassium hydroxide aqueous solution.
[0076] The heteropolyacid catalyst is tetrakis(hexadecyltrimethylammonium)octamolybdate.
[0077] The time for adding the heteropolyacid catalyst dropwise is 2 hours.
[0078] The concentration of the hydrogen peroxide solution is 30 wt %.
[0079] The post-treatment comprises the following steps: filtering to remove the catalyst, adding concentrated hydrochloric acid (37 wt %) to acidify to pH=1.5, filtering, rinsing and drying to obtain the sulfonepyraclostrobin metabolite M3.
[0080] Comparative Example 2
[0081] Comparative Example 2 of the present invention provides a method for preparing a sulfonepyraclostrobin metabolite M3, comprising the following steps: placing 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole (200 g, 0.8 mmol, 1 eq.) and an alkaline aqueous solution (769.22 g, 1.83 mol, 2.3 eq.) in a reaction vessel, heating to 70° C., adding a heteropolyacid catalyst (10 g) and immediately adding dropwise hydrogen peroxide (135.37 g, 1.19 mol, 1.5 eq.); after the addition is completed, the mixture is kept warm at 70° C. for 1 h, and the sulfonepyraclostrobin metabolite M3 (150.27 g, content 89.32 wt%, yield 64.8%) is obtained through post-treatment.
[0082] The alkaline aqueous solution is a 5 wt % sodium hydroxide aqueous solution.
[0083] The heteropolyacid catalyst is tetrakis(1-benzyl-3-methylimidazolium)octamolybdate.
[0084] The time for adding the heteropolyacid catalyst dropwise is 2 hours.
[0085] The concentration of the hydrogen peroxide solution is 30 wt %.
[0086] The post-treatment comprises the following steps: filtering to remove the catalyst, adding concentrated hydrochloric acid (37 wt %) to acidify to pH=1.5, filtering, rinsing and drying to obtain the sulfonepyraclostrobin metabolite M3.
[0087] Comparative Example 3
[0088] Comparative Example 3 of the present invention provides a method for preparing a sulfonepyraclostrobin metabolite M3, comprising the following steps: placing 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole (200 g, 0.8 mmol, 1 eq.) and an alkaline aqueous solution (135.37 g, 1.19 mol, 1.5 eq.) in a reaction vessel, heating to 80° C., adding a heteropolyacid catalyst (3.33 g) and immediately adding dropwise hydrogen peroxide (135.37 g, 1.19 mol, 1.5 eq.); after the addition is completed, the mixture is kept warm at 85° C. for 1 hour, and the sulfonepyraclostrobin metabolite M3 (144.53 g, content 80.11 wt%, yield 55.9%) is obtained through post-treatment.
[0089] The alkaline aqueous solution is a 10 wt % sodium hydroxide aqueous solution.
[0090] The heteropolyacid catalyst is tetrakis(1-ethylpyridinium) decatungstate.
[0091] The time for adding the heteropolyacid catalyst dropwise is 2 hours.
[0092] The concentration of the hydrogen peroxide solution is 30 wt %.
[0093] The post-treatment comprises the following steps: filtering to remove the catalyst, adding concentrated hydrochloric acid (37 wt %) to acidify to pH=1.5, filtering, rinsing and drying to obtain the sulfonepyraclostrobin metabolite M3.
Claims
1. A method for preparing a sulfonepyraclostrobin metabolite M3, characterized in that: At least the following steps are included: 1-Methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole and an alkaline aqueous solution are placed in a reaction vessel, the temperature is raised to 70-90°C, and hydrogen peroxide is immediately added dropwise after the heteropolyacid catalyst is added; after the addition is completed, the temperature is kept at 70-95°C for 0.5-1h, and the sulfonepyrazoline metabolite M3 is obtained through post-treatment.
2. The method for preparing the sulfonepyraclostrobin metabolite M3 according to claim 1, characterized in that: The solute in the alkaline aqueous solution is at least one of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate.
3. The method for preparing the sulfonepyraclostrobin metabolite M3 according to claim 1, characterized in that: The concentration of the alkaline aqueous solution is 3 to 25 wt %.
4. The method for preparing the sulfonepyraclostrobin metabolite M3 according to claim 1, characterized in that: The heteropolyacid catalyst is selected from tetrakis(1-propyl-3-methylimidazolium)octamolybdate, tetrakis(1-propyl-3-methylimidazolium)decatungstate, tetrakis(1-hexadecyl-3-methylimidazolium)octamolybdate, tetrakis(1-hexadecyl-3-methylimidazolium)decatungstate, tetrakis(1-benzyl-3-methylimidazolium)octamolybdate, tetrakis(1-benzyl-3-methylimidazolium)decatungstate, tetrakis(hexadecyltrimethylammonium) At least one of octamolybdate, tetrakis(hexadecyltrimethylammonium) decatungstate, tetrakis(1-butyl-3-methylpyridinium) octamolybdate, tetrakis(1-butyl-3-methylpyridinium) decatungstate, tetrakis(1-butyl-4-methylpyridinium) octamolybdate, tetrakis(1-butyl-4-methylpyridinium) decatungstate, tetrakis(1-ethylpyridinium) octamolybdate, tetrakis(1-ethylpyridinium) decatungstate, and tetrabutylammonium decatungstate.
5. The method for preparing the sulfonepyraclostrobin metabolite M3 according to claim 4, characterized in that: The heteropolyacid catalyst is one of tetrakis(1-hexadecyl-3-methylimidazolium)octamolybdate, tetrabutylammonium decatungstate or tetrakis(1-ethylpyridinium)octamolybdate.
6. The method for preparing the sulfonepyraclostrobin metabolite M3 according to claim 1, characterized in that: The molar ratio of the 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole, the alkaline aqueous solution and the hydrogen peroxide is 1: (0.9-2.5): (1-6).
7. The method for preparing the sulfonepyraclostrobin metabolite M3 according to claim 1, characterized in that: The mass ratio of the heteropolyacid catalyst to 1-methyl-3-trifluoromethyl-4-hydroxymethyl-5-difluoromethoxy-1-H-pyrazole is 1:(10-60).
8. The method for preparing the sulfonepyraclostrobin metabolite M3 according to claim 1, characterized in that: The time for adding the heteropolyacid catalyst dropwise is 1.5-2.5 hours.
9. The method for preparing the sulfonepyraclostrobin metabolite M3 according to claim 1, characterized in that: The concentration of the hydrogen peroxide is 20-40 wt %.
10. The method for preparing the sulfonepyraclostrobin metabolite M3 according to claim 1, characterized in that: The post-treatment comprises the following steps: filtering to remove the catalyst, adding concentrated hydrochloric acid to acidify to pH=1-2, filtering, rinsing and drying to obtain the sulfonepyraclostrobin metabolite M3.