Preparation method and application of a double-amide compound with high insecticidal activity

Abstract

This invention provides a method for preparing and applying a highly insecticidal diamide compound, relating to the chemical and pesticide fields. The method includes: reacting 2-fluoro-3-nitrobenzoic acid with thionyl chloride (a chlorinating agent) and dimethylformamide (a catalyst) to obtain compound A; condensing compound A with 2-trifluoromethyl-4-heptafluoroisopropyl-6-bromoaniline amide to obtain compound B; reducing compound B to obtain compound C; and, during the reaction under a hydrogen atmosphere, determining the reaction temperature and hydrogen flow rate in each hydrogenation reaction zone based on the concentration of compound B; reacting compound C with paraformaldehyde to obtain compound D; chlorinating 3-chloro-4-fluorobenzoic acid with thionyl chloride (a chlorinating agent) and dimethylformamide (a catalyst) to obtain compound E; and amide condensing compound E with compound D to obtain the novel diamide compound of this invention. The diamide compound of this invention exhibits excellent insecticidal effects when used in pesticide compositions.

Description

Technical Field

[0001] This invention relates to the fields of chemical and pesticide technology, specifically to a method for preparing and applying a diamide compound with high insecticidal activity. Background Technology

[0002] m-Diamide compounds, represented by Brofenanilide, are increasingly becoming a research hotspot for pesticide companies due to their unique mechanism of action, novel target sites, and environmental friendliness. Studies have shown that Brofenanilide is an allosteric regulator of GABA-gated chloride channels (also known as ionotropic GABA receptors), primarily acting on a unique binding site on this channel to inhibit chloride ion translocation into the cell, leading to hyperexcitability or spasm in insects, thus exhibiting rapid insecticidal activity. Existing methods for preparing m-diamid compounds, such as CN112707836A (a method for preparing a m-diamid compound), have the following problems: 1. In the hydrogenation reaction, only the reaction temperature range after hydrogen is introduced is given, but the specific application process for determining the temperature of the hydrogenation reaction is not given. Different raw materials (even the same raw material) may have different temperatures. Giving only a fixed temperature range may lead to incomplete reaction or aggravated side reactions due to inaccurate temperature determination, which will affect the stability of product quality. 2. Furthermore, the hydrogen replenishment flow rate for the hydrogenation reaction section (stage) is not determined, which can easily lead to hydrogen waste or uncontrolled reaction rate, making it difficult to achieve precise process control. Summary of the Invention

[0003] This invention provides a method for preparing and applying a diamide compound with high insecticidal activity, in order to solve the technical problems mentioned in the background art.

[0004] To address the aforementioned technical problems, this invention discloses a method for preparing a diamide compound with high insecticidal activity, comprising: Step 1: Add 2-fluoro-3-nitrobenzoic acid, thionyl chloride and dimethylformamide sequentially to the reactor, then heat the reaction, remove thionyl chloride under reduced pressure to obtain acyl chloride, add dichloroethane to dissolve, and obtain a dichloroethane solution containing compound A; Step 2: Add sodium bicarbonate and 2-trifluoromethyl-4-heptafluoroisopropyl-6-bromoaniline to the material obtained in Step 1, then heat the mixture to react. After the reaction is complete, cool the mixture and add water to wash the product. Separate the liquid and evaporate the organic phase to dryness to obtain compound B. Step 3: Add compound B obtained in step 2 into the reactor, then add anhydrous ethanol and 5% palladium on carbon in sequence, and detect the concentration of compound B. Then replace the gas in the reactor. After the reaction is completed under a hydrogen atmosphere, filter and evaporate to obtain compound C. During the reaction under a hydrogen atmosphere, the reaction temperature and the hydrogen addition flow rate in each hydrogenation reaction section are determined based on the concentration of compound B. Step 4: Add concentrated sulfuric acid to the reactor, then control the temperature and add formaldehyde aqueous solution. After the reaction is completed, cool down and pour the reaction solution into ice water. After the solid precipitates, filter and wash with water. Dry the washed solid to obtain compound D. Step 5: Add toluene, 3-chloro-4-fluorobenzoic acid, thionyl chloride and dimethylformamide back into the reactor in sequence, heat and maintain the temperature until all are dissolved, and after the reaction is completed, remove the toluene solution containing compound E by vacuum distillation. Step 6: Add compound D to the material obtained in step 5, then heat the mixture to react. After the reaction is complete, pour the reaction solution into ice water, the solid precipitates out and is filtered and washed to obtain a diamide compound with high insecticidal activity.

[0005] Preferably, the weight ratio of anhydrous ethanol, 5% palladium on carbon, and thionyl chloride added to the reactor in step 3 is 200:1:100.

[0006] Preferably, for different concentration ranges of compound B, the baseline parameter set corresponding to qualified production is determined by combining experimental calibration with historical production data. The baseline parameter set includes: the baseline hydrogen consumption rate ratio range for each hydrogenation reaction section, the baseline average hydrogen consumption rate range for a set time period under different pressure and temperature groups; the "baseline average hydrogen consumption rate - baseline hydrogen inflow rate" rule for the hydrogenation reaction section corresponding to the set time period; and all temperature values ​​in the pressure and temperature group are in the range of 30℃ to 35℃. In step 3: Step 31: Add compound B obtained in step 2 into the reactor, then add anhydrous ethanol and 5% palladium on carbon in sequence, and detect the concentration of compound B; Step 32: Replace the gas in the reactor; Step 33: Control the hydrogen pressure to 0.3 MPa and the reaction temperature to 30°C to start the hydrogen addition reaction. Determine the actual average hydrogen consumption rate for the current set time period and compare it with the benchmark average hydrogen consumption rate range of [30°C, 0.3 MPa] to determine the rate deviation value. Based on the rate deviation, determine the corrected pressure and temperature group and the required hydrogen addition flow rate according to the correction strategy. Step 34: Based on the corrected pressure and temperature set and the required hydrogen addition flow rate determined in Step 33, continue the hydrogenation reaction.

[0007] Preferably, the pressure-temperature group includes: [30℃, 0.3MPa], [31℃, 0.3MPa], [32℃, 0.3MPa], [33℃, 0.3MPa], [34℃, 0.3MPa], [35℃, 0.3MPa].

[0008] Preferably, in step 33: Rate deviation value = (actual average hydrogen consumption rate - V) ÷ V; Among them, the half-width of the baseline average hydrogen consumption rate interval [30℃, 0.3MPa] is determined and denoted as B; And determine the comparison ratio of the median of the baseline average hydrogen consumption rate interval for other pressure and temperature groups to V; The median of the baseline average hydrogen consumption rate range [30℃, 0.3 MPa] is denoted as V; If the rate deviation is less than or equal to B / V, the corrected pressure and temperature group remains at [30℃, 0.3MPa]. The required hydrogen addition flow rate for the first hydrogenation reaction section is determined based on the actual average hydrogen consumption rate and the aforementioned pattern during the current set time period in step 33. If the rate deviation value is greater than B / V, an alarm will be triggered; If the rate deviation value is less than -B / V, the pressure and temperature group with a control ratio >1 and matching the rate deviation value is selected as the correction pressure and temperature group; and the required hydrogen addition flow rate of the first hydrogenation reaction section is determined based on the actual average hydrogen consumption rate of the current set time period in step 33 and the aforementioned pattern. The required hydrogen injection flow rate for the remaining hydrogenation reaction sections is determined based on the required hydrogen injection flow rate for the first hydrogenation reaction section.

[0009] Preferably, the structural formula of compound A is as follows: The structural formula of compound B is The structural formula of compound C is The structural formula of compound D is The structural formula of compound E is The structural formula of the diamide compound with high insecticidal activity of the present invention is as follows: .

[0010] Preferably, in step 1, the weight ratio of 2-fluoro-3-nitrobenzoic acid, thionyl chloride, and dimethylformamide added to the reactor is 18.5:100:1. The mixture is then heated to 80°C and reacted for 6 hours. The thionyl chloride is removed under reduced pressure to obtain acyl chloride. The weight ratio of dichloroethane added to the acyl chloride is the same as the weight ratio of thionyl chloride added to the reactor. In step 2, the weight ratio of sodium bicarbonate, 2-trifluoromethyl-4-heptafluoroisopropyl-6-bromoaniline added to the dichloroethane solution containing compound A, and the weight ratio of thionyl chloride added to the reactor in step 1 is 12.7:40.8:100. After reacting at 70°C for 8 hours, the weight ratio of water added to the dichloroethane solution containing compound A, and the weight ratio of sodium bicarbonate added to the solution is 50:12.7.

[0011] Preferably, the weight ratio of concentrated sulfuric acid added to the reactor in step 4 to thionyl chloride added to the reactor in step 1 is 150:100, the temperature is controlled at 30℃-35℃, the weight ratio of formaldehyde aqueous solution added to the reactor to concentrated sulfuric acid added to the reactor is 12.96:150, and after the reaction is completed, the temperature is cooled to room temperature.

[0012] Preferably, the weight ratio of toluene, 3-chloro-4-fluorobenzoic acid, thionyl chloride, dimethylformamide, and thionyl chloride added to the reactor in step 5 is 90:15.3:11.4:0.0948:100, and the temperature is raised to 90°C and reacted for 6 hours. In step 6, compound D was added to the toluene solution containing compound E in three portions. The total weight ratio of compound D to thionyl chloride added to the reactor in step 1 was 45:100. The mixture was then heated to 105°C and refluxed for 8 hours. After the reaction was completed, the reaction solution was gradually cooled to room temperature. The solid precipitated and was filtered and washed twice to obtain a white solid.

[0013] A highly insecticidal diamide compound prepared using the aforementioned method is used to control crop pests, specifically thrips.

[0014] The technical solution of the present invention will be further described in detail below with reference to the accompanying drawings and embodiments.

[0015] Compared with the prior art, the present invention has the following beneficial effects: 1. The diamide compound with high insecticidal activity prepared by this invention is used in pesticide compositions, and its control efficacy is as high as 100%, the crop growth is good, and the insecticidal effect is excellent. This invention has excellent insecticidal effect on crop pests such as rose thrips, and the effect is long-lasting. It is also safe for roses and the effect is significantly better than the prior art. The diamide compound prepared by this invention has a purity of up to 98% and a yield of 88%.

[0016] 2. Existing technologies only provide a broad temperature range, which can easily lead to incomplete reactions or aggravated side reactions due to inaccurate temperature readings, affecting product quality. In this invention, the hydrogenation reaction temperature and the hydrogen flow rate in each hydrogenation reaction section are dynamically determined based on the concentration of compound B. Appropriate reaction conditions can be matched in real time according to the raw material concentration to ensure quality and significantly improve product quality stability.

[0017] 3. Existing technologies do not clearly define the hydrogen replenishment flow rate in the hydrogenation reaction section, which can easily lead to hydrogen waste or uncontrolled reaction rate, making it difficult to ensure the reaction is qualified. This invention achieves fine-grained control of the reaction rate by precisely setting the hydrogen addition flow rate according to the hydrogenation reaction section and correlating it with the concentration of compound B. This avoids the ineffective consumption of hydrogen and ensures a stable and controllable reaction rate.

[0018] By linking the reaction temperature and hydrogen flow rate to the feed concentration, the hydrogenation process of this invention has greater adaptability. Even if there are differences in feed batches or concentrations, dynamic adjustments can be made to ensure that the reaction process meets the qualification standards. Attached Figure Description

[0019] The accompanying drawings are provided to further illustrate the invention and form part of the specification. They are used in conjunction with embodiments of the invention to explain the invention and do not constitute a limitation thereof. In the drawings: Figure 1 This is a schematic diagram of the process of the present invention. Detailed Implementation

[0020] The preferred embodiments of the present invention will be described below with reference to the accompanying drawings. It should be understood that the preferred embodiments described herein are for illustration and explanation only and are not intended to limit the present invention.

[0021] Furthermore, in this invention, the use of terms such as "first" and "second" is for descriptive purposes only and does not specifically refer to any order or sequence, nor is it intended to limit the invention. They are merely used to distinguish components or operations described using the same technical terms and should not be construed as indicating or implying relative importance or implicitly specifying the number of indicated technical features. Therefore, a feature defined with "first" or "second" may explicitly or implicitly include at least one of those features. Additionally, the technical solutions and features of the various embodiments can be combined with each other, but this must be based on the ability of those skilled in the art to implement them. If a combination of technical solutions is contradictory or impossible to implement, it should be considered that such a combination of technical solutions does not exist and is not within the scope of protection claimed by this invention.

[0022] The present invention provides the following embodiments: Example 1: This embodiment of the invention provides a needle-punching simulation injector, such as... Figure 1 As shown, it includes: Step 1: Add 2-fluoro-3-nitrobenzoic acid, thionyl chloride and dimethylformamide sequentially to a reactor (which may be a reaction vessel, reaction kettle, etc.), then heat the reaction, remove thionyl chloride under reduced pressure to obtain acyl chloride, add dichloroethane to dissolve it, and obtain a dichloroethane solution containing compound A. Step 2: Add sodium bicarbonate and 2-trifluoromethyl-4-heptafluoroisopropyl-6-bromoaniline to the material obtained in Step 1, then heat the mixture to react. After the reaction is complete, cool the mixture and add water to wash the product. Separate the liquid and evaporate the organic phase to dryness to obtain compound B. Step 3: Add compound B obtained in step 2 into the reactor, then add anhydrous ethanol and 5% palladium on carbon in sequence, and detect the concentration of compound B. Then replace the gas in the reactor. After the reaction is completed under a hydrogen atmosphere, filter and evaporate to obtain compound C. During the reaction under a hydrogen atmosphere, the reaction temperature and the hydrogen addition flow rate in each hydrogenation reaction section are determined based on the concentration of compound B. Step 4: Add concentrated sulfuric acid to the reactor, then control the temperature and add formaldehyde aqueous solution. After the reaction is completed, cool down and pour the reaction solution into ice water. After the solid precipitates, filter and wash with water. Dry the washed solid to obtain compound D. Step 5: Add toluene, 3-chloro-4-fluorobenzoic acid, thionyl chloride and dimethylformamide back into the reactor in sequence, heat and maintain the temperature until all are dissolved, and after the reaction is completed, remove the toluene solution containing compound E by vacuum distillation. Step 6: Add compound D to the material obtained in step 5, then heat the mixture to react. After the reaction is complete, pour the reaction solution into ice water, the solid precipitates out and is filtered and washed to obtain a diamide compound with high insecticidal activity.

[0023] The structural formula of compound A is The structural formula of compound B is The structural formula of compound C is The structural formula of compound D is The structural formula of compound E is The structural formula of the diamide compound with high insecticidal activity of the present invention is as follows: .

[0024] The reaction formula for the yield of compound A in step 1, where 2-fluoro-3-nitrobenzoic acid reacts with chlorinating agent thionyl chloride and catalyst dimethylformamide, is as follows: ; The reaction formula for the condensation reaction of compound A with 2-trifluoromethyl-4-heptafluoroisopropyl-6-bromoaniline amide in step 2 to obtain compound B is as follows: ; The reaction equation for the reduction of compound B to obtain compound C in step 3 is as follows: ; The reaction equation for the substitution reaction between compound C and paraformaldehyde in step 4 to obtain compound D is as follows: ; In step 5, 3-chloro-4-fluorobenzoic acid reacts with thionyl chloride as a chlorinating agent and dimethylformamide as a catalyst to give compound E. The reaction formula is as follows: ; The reaction formula for the amide condensation reaction between compound E and compound D in step 6 to obtain the novel diamide compound of this invention is as follows: .

[0025] The beneficial effects of the above scheme are as follows: 1. The diamide compound with high insecticidal activity prepared by this invention is used in pesticide compositions, and its control efficacy is as high as 100%, the crop growth is good, and the insecticidal effect is excellent. This invention has excellent insecticidal effect on crop pests such as rose thrips, and the effect is long-lasting. It is also safe for roses and the effect is significantly better than the prior art. The diamide compound prepared by this invention has a purity of up to 98% and a yield of 88%.

[0026] 2. Existing technologies only provide a broad temperature range, which can easily lead to incomplete reactions or aggravated side reactions due to inaccurate temperature readings, affecting product quality. In this invention, the hydrogenation reaction temperature and the hydrogen flow rate in each hydrogenation reaction section are dynamically determined based on the concentration of compound B. Appropriate reaction conditions can be matched in real time according to the raw material concentration to ensure quality and significantly improve product quality stability.

[0027] 3. Existing technologies do not clearly define the hydrogen replenishment flow rate in the hydrogenation reaction section, which can easily lead to hydrogen waste or uncontrolled reaction rate, making it difficult to ensure the reaction is qualified. This invention achieves fine-grained control of the reaction rate by precisely setting the hydrogen addition flow rate according to the hydrogenation reaction section and correlating it with the concentration of compound B. This avoids the ineffective consumption of hydrogen and ensures a stable and controllable reaction rate.

[0028] By linking the reaction temperature and hydrogen flow rate to the feed concentration, the hydrogenation process of this invention has greater adaptability. Even if there are differences in feed batches or concentrations, dynamic adjustments can be made to ensure that the reaction process meets the qualification standards.

[0029] Based on Example 1, a specific example is as follows: In step 1, the weight ratio of 2-fluoro-3-nitrobenzoic acid, thionyl chloride, and dimethylformamide added to reaction flask 1 is 18.5:100:1. Then, the temperature is raised to 80°C and reacted for 6 hours. The thionyl chloride is removed by vacuum distillation to obtain acyl chloride. The weight ratio of dichloroethane added to the acyl chloride is the same as that of thionyl chloride added to reaction flask 1. In step 2, the weight ratio of sodium bicarbonate, 2-trifluoromethyl-4-heptafluoroisopropyl-6-bromoaniline, and thionyl chloride added to reaction flask 1 in step 1 is 12.7:40.8:100. After reacting at 70°C for 8 hours, the weight ratio of water added and sodium bicarbonate added to the dichloroethane solution containing compound A is 50:12.7. In step 3, the weight ratio of anhydrous ethanol, 5% palladium on carbon, and thionyl chloride added to reaction flask 1 in step 1 is 200:1:100. The gas in reaction flask 1 is replaced three times with nitrogen. Then, hydrogen is injected into reaction flask 1 at a pressure of p=0.3MPa. The reaction is carried out for 4 hours in a hydrogen atmosphere at a temperature of 30℃-35℃. In step 4, the weight ratio of concentrated sulfuric acid added to reaction flask 1 to thionyl chloride added to reaction flask 1 in step 1 is 150:100. The temperature is controlled at 30℃-35℃. The weight ratio of formaldehyde aqueous solution added to reaction flask 1 to concentrated sulfuric acid added to reaction flask 1 is 12.96:150. After the reaction is completed, the temperature is lowered to room temperature. In step 5, the weight ratio of toluene, 3-chloro-4-fluorobenzoic acid, thionyl chloride, dimethylformamide, and thionyl chloride added to reaction flask 1 in step 1 is 90:15.3:11.4:0.0948:100. The mixture is heated to 90°C and reacted for 6 hours. In step 6, compound D was added to the toluene solution containing compound E in three portions. The total weight ratio of compound D added to thionyl chloride added to reaction flask 1 in step 1 was 45:100. The mixture was then heated to 105°C and refluxed for 8 hours. After the reaction was completed, the reaction solution was gradually cooled to room temperature. The solid precipitated and was filtered and washed twice to obtain an off-white solid.

[0030] Specifically, 2-fluoro-3-nitrobenzoic acid (18.5 g, 100.0 mmol), 100 g of thionyl chloride, and 1 g of dimethylformamide were added to reaction flask 1. The mixture was heated to 80 °C and reacted for 6 hours. The thionyl chloride was removed by vacuum distillation to obtain acyl chloride. Then, 100 g of dichloroethane, 12.7 g of sodium bicarbonate (120 mmol), and 40.8 g of 2-trifluoromethyl-4-heptafluoroisopropyl-6-bromoaniline (40.8 g, 100 mmol) were added sequentially to the obtained acyl chloride. The mixture was heated to 70 °C and reacted for 8 hours. After monitoring the reaction to complete, 50 g of water was added, and the mixture was stirred and separated. The organic phase was evaporated to dryness to obtain compound B. Add 200g of anhydrous ethanol and 1g of 5% palladium on carbon to compound B. Purge the mixture three times with nitrogen and react for 4 hours at a hydrogen pressure of 0.3MPa and a temperature of 30℃-35℃. After the reaction is complete, filter the reaction solution and evaporate to dryness to obtain the crude product, compound C. Add 150g of concentrated sulfuric acid to compound C, stir to dissolve, and maintain the temperature at 30℃-35℃. Slowly add 12ml of formaldehyde aqueous solution (0.13mmol). After the addition is complete, raise the temperature to 40℃ and continue the reaction. Monitor the reaction by TLC until it is complete. After cooling to room temperature, slowly pour the reaction solution into 300mL of ice water, stir thoroughly, and precipitate a solid. Filter, wash with water, and dry the solid. The steps resulted in the final yield of 45g of a pale yellow solid with a purity of 96%, which was identified as compound D. Then, toluene (90g), 3-chloro-4-fluorobenzoic acid (15.3g, 88mmol), thionyl chloride (11.4g, 97mmol), and 3 drops (0.094ml) of dimethylformamide were added sequentially to reaction flask 1. The mixture was gradually heated to 90℃ and reacted for 6 hours until completely dissolved. The dissolved substance was removed by vacuum evaporation, yielding an oily substance, which was then redissolved in 90g of toluene to obtain a toluene solution containing compound E. Compound D (45g, 80mmol) was then added to the toluene solution containing compound E in three batches, with the temperature gradually increased to 1℃. The reaction was carried out under micro-reflux at 05℃ for 8 hours. After monitoring the end of the reaction, the temperature was gradually lowered to room temperature, and a solid precipitated out. The solid was filtered through toluene and washed twice to obtain an off-white solid. After drying, 50.4 g of N-(2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-(N-methyl-4-fluoro-3-chlorobenzamide)benzamide, a highly insecticidal diamide compound of the present invention, was obtained with a purity of 98% and a yield of 88%. Multiple reaction flasks 1 can be used to prepare the highly insecticidal diamide compound of the present invention. For example, the reaction flask 1 used in step 1 and the reaction flask 1 used in step 5 are not the same reaction flask 1.

[0031] Example 2: Based on Example 1, for different concentration ranges of compound B, the baseline parameter set corresponding to qualified production was determined by combining experimental calibration with historical production data. The baseline parameter set includes: the baseline hydrogen consumption rate ratio interval for each hydrogenation reaction section (the interval of the hydrogen consumption rate ratio between the second hydrogenation reaction section and the first hydrogenation rate ratio interval, and the interval of the hydrogen consumption rate ratio between the third hydrogenation reaction section and the first hydrogenation rate ratio interval); the baseline average hydrogen consumption rate interval for a set time period under different pressure and temperature groups; the "baseline average hydrogen consumption rate - baseline hydrogen injection flow rate" rule for the hydrogenation reaction section corresponding to the set time period; and all temperature values ​​in the pressure and temperature group are within the range of 30℃ to 35℃. The pressure and temperature groups include: [30℃, 0.3Mpa], [31℃, 0.3Mpa], [32℃, 0.3Mpa], [33℃, 0.3Mpa], [34℃, 0.3Mpa], and [35℃, 0.3Mpa].

[0032] In step 3: Step 31: Add compound B obtained in step 2 into the reactor, then add anhydrous ethanol and 5% palladium on carbon in sequence, and detect the concentration of compound B; Step 32: Replace the gas in the reactor (using nitrogen). Step 33: Control the hydrogen pressure to 0.3 MPa and the reaction temperature to 30°C to start the hydrogen addition reaction. Determine the actual average hydrogen consumption rate for the current set time period and compare it with the benchmark average hydrogen consumption rate range of [30°C, 0.3 MPa] to determine the rate deviation value. Based on the rate deviation, determine the corrected pressure and temperature group and the required hydrogen addition flow rate according to the correction strategy. Step 34: Based on the corrected pressure and temperature set and the required hydrogen addition flow rate determined in Step 33, continue the hydrogenation reaction.

[0033] In step 33: Rate deviation value = (actual average hydrogen consumption rate - V) ÷ V; Among them, the half-width of the baseline average hydrogen consumption rate interval [30℃, 0.3MPa] is determined and denoted as R; And determine the comparison ratio of the median of the baseline average hydrogen consumption rate interval for other pressure and temperature groups to V; for example, the comparison ratio for the pressure and temperature group [32℃, 0.3MPa] is: median of the baseline average hydrogen consumption rate interval for the pressure and temperature group [32℃, 0.3MPa] ÷ V. The median of the baseline average hydrogen consumption rate range [30℃, 0.3 MPa] is denoted as V; The correction strategy is as follows: If the rate deviation is less than or equal to R / V, the corrected pressure and temperature group remains [30℃, 0.3MPa], and the required hydrogen injection flow rate for the first reaction section follows the baseline value under this pressure and temperature group ([30℃, 0.3MPa]). The required hydrogen input flow rate for the remaining reaction sections is determined based on the corresponding baseline hydrogen consumption rate ratio interval for each hydrogenation reaction section. For example, the required hydrogen input flow rate for reaction section 2 = the required hydrogen input flow rate for reaction section 1 × the median of the baseline hydrogen consumption rate ratio interval for reaction section 2 ÷ the median of the baseline hydrogen consumption rate ratio interval for reaction section 1. If the rate deviation value is greater than R / V, an alarm will be triggered, indicating an abnormal operating condition and a safety or quality risk. An inspection and adjustment will be prompted. The reaction rate should be suppressed first by reducing the reaction temperature (e.g., from 30℃ to 28℃), reducing the stirring rate, or suspending the raw material feeding. If the rate deviation is less than -B / V, the pressure and temperature group with a reference ratio > 1 and matching the rate deviation is selected as the correction pressure and temperature group; and the required hydrogen inlet flow rate for the first hydrogenation reaction section is determined based on the actual average hydrogen consumption rate of the current set time period in step 33 and the aforementioned pattern; the required hydrogen inlet flow rate for the remaining hydrogenation reaction sections is determined based on the required hydrogen inlet flow rate for the first hydrogenation reaction section; the required hydrogen inlet flow rate for the remaining reaction sections is still adjusted synchronously according to the above-mentioned proportional relationship of "reference hydrogen consumption rate ratio interval".

[0034] The target pressure-temperature group satisfies: the control ratio of the target pressure-temperature group × It should be a pressure-temperature group with a value greater than 1 and the smallest or second smallest control ratio; For example: First reaction zone: Initial concentration of compound B to 0.6 times the concentration of compound B (0.4 → 0.24 mol / L); baseline hydrogen consumption rate: 12–14 mL / min; Second reaction zone: 0.6 times the concentration of compound B to 0.2 times the concentration of compound B (0.24→0.08 mol / L); baseline hydrogen consumption rate: 12–13 mL / min, corresponding to a baseline hydrogen consumption rate ratio range of 0.95–1.05; The third reaction zone: from 0.2 times the concentration of compound B to the reaction endpoint (0.08→0.004mol / L); baseline hydrogen consumption rate: 6–7mL / min, corresponding to a baseline hydrogen consumption rate ratio range of 0.45–0.55; For example, in the first reaction zone: 12–14 mL / min; the baseline hydrogen consumption rate is 12 mL / min, corresponding to a baseline hydrogen inlet flow rate of 12.6 mL / min; the baseline hydrogen consumption rate is 13 mL / min, corresponding to a baseline hydrogen inlet flow rate of 13.65 mL / min; the baseline hydrogen consumption rate is 14 mL / min, corresponding to a baseline hydrogen inlet flow rate of 14.7 mL / min.

[0035] In actual mass production, when the baseline hydrogen consumption rate of the hydrogenation reaction section does not meet the requirements of the range, an early warning will be issued to remind adjustments.

[0036] 1. The baseline hydrogen consumption rate ratio of the current hydrogenation reaction section = the average of the baseline hydrogen consumption rates of the current hydrogenation reaction section ÷ the maximum of the average of the baseline hydrogen consumption rates of all hydrogenation reaction sections; corresponding to the same overall reaction process; The baseline average hydrogen consumption rate for a set time period under different pressure and temperature groups: For each batch of raw materials, under a specific concentration range of compound B, the pressure and temperature group that meets the production requirements in step 3 is selected as the qualified pressure and temperature group, and the calibrated average hydrogen consumption rate for the set time period corresponding to the qualified pressure and temperature group is determined. The set time period is for reaction zone 1, which is a period of time after the reaction starts; the recommended set time range is 2 to 5 minutes, which can effectively filter instantaneous fluctuations and ensure timely system response.

[0037] By combining experimental calibration with historical production data, the baseline parameter set corresponding to qualified production is determined as follows: In the early stage, the "compound B concentration range + qualified pressure and temperature group + baseline rate range + rate-flow rate law" are all calibrated through historical qualified batches, forming a fixed baseline database. In subsequent production, each batch of raw materials is no longer calibrated batch by batch. It is only necessary to detect the concentration of compound B in the current batch and directly retrieve it from the database and combine it with the baseline parameters of the corresponding concentration range for real-time control (the parameters can also be adjusted according to the actual reaction process until step 3 is qualified). During continuous production, the production data of newly generated qualified batches are automatically included in the baseline database for fusion calculation according to a preset cycle (such as monthly or every 50 batches) to iteratively optimize the baseline parameter set and ensure that the database always keeps up with the latest production conditions.

[0038] The frequency and stability of each temperature and pressure group in qualified batches were statistically analyzed. The temperature and pressure group with the highest frequency and the most stable product quality was selected as the qualified pressure and temperature group for that concentration range.

[0039] For a specific concentration range and pressure-temperature group, hydrogen consumption rate data from all qualified batches within a set time period are collected. For each batch, the average hydrogen consumption rate within the set time period is calculated; obviously abnormal data (such as deviations from the mean by more than 3σ) are removed; the mean μ and standard deviation σ are calculated for the remaining data. A 95% confidence interval or a ±2σ interval is used as the baseline average hydrogen consumption rate interval for the specific concentration range and pressure-temperature group. Under each "compound B concentration range + qualified pressure and temperature group", discrete data pairs of the baseline average hydrogen consumption rate and the corresponding hydrogen injection flow rate within a set time period are extracted from qualified batches. These data pairs are categorized and organized according to rate ranges and solidified into discrete rate-flow rate correspondence tables as rate-flow rate laws. Finally, the concentration ranges, qualified temperature and pressure groups, baseline average hydrogen consumption rate ranges, baseline hydrogen consumption rate ratio ranges for each segment, and the above discrete rate-flow rate laws are hierarchically integrated to construct a structured benchmark database.

[0040] The baseline average hydrogen consumption rate (which can be a range) minus the baseline hydrogen inlet flow rate (which can also be a range) is defined as follows: For example, if the baseline average hydrogen consumption rate for a certain range is A, and the hydrogen pressure does not meet the target hydrogen pressure (e.g., 0.3 MPa) within this range, the hydrogen pressure will return to the target hydrogen pressure (e.g., 0.3 MPa) within a specified time range (e.g., 1–3 minutes) at the corresponding baseline hydrogen inlet flow rate, thus satisfying the reaction kinetics requirements. On the other hand, it allows the hydrogen partial pressure to recover to a level that meets the reaction requirements, ensuring mass transfer efficiency and ultimately achieving stable reaction and qualified product quality. The specified time range within this range represents the time interval during which the vast majority of qualified batches (e.g., over 90%; if the qualified batch is determined experimentally to be qualified within this time range) complete pressure recovery.

[0041] The beneficial effects of the above scheme are: The baseline database was solidified in the early stages by utilizing historical qualified batches and experimental phases. Subsequent production no longer requires batch-by-batch calibration; only the concentration of compound B in the current batch needs to be measured to directly access the corresponding baseline parameters, significantly improving production efficiency. Furthermore, since the actual raw material conditions of different application batches are random and uncertain, the above calibration ensures the rapid and accurate determination of appropriate parameters for each specific batch, guaranteeing production qualification rates and avoiding the problem of requiring numerous experiments for each batch during calibration.

[0042] Using the median V and half-width R of the baseline average hydrogen consumption rate interval under the [30℃, 0.3MPa] condition as the basis for deviation judgment makes the calculation and correction strategy of rate deviation more accurate. The comparison ratio of the median of the baseline average hydrogen consumption rate interval to V for different pressure and temperature groups provides a reliable basis for the selection of target conditions, ensuring that the corrected conditions can effectively improve reaction efficiency without deviating from safety and quality boundaries.

[0043] The corrected pressure and temperature set and hydrogen injection flow rate follow the rate-flow rate law and rate ratio relationship of each segment in the baseline parameter set, forming a closed-loop control of "detection-correction-execution" for the subsequent hydrogenation reaction, ensuring that the reaction process always operates under optimal and safest conditions. The correspondence between the baseline average hydrogen consumption rate and the hydrogen injection flow rate ensures that the hydrogen partial pressure returns to the target pressure within a specified time, ultimately achieving stable reaction and qualified product quality.

[0044] For the first time, the matching of "rate-flow rate-pressure recovery time" has been achieved, which not only ensures the requirements of reaction kinetics, but also avoids pressure shock caused by excessive flow rate or reaction lag caused by insufficient flow rate.

[0045] 4. After maintaining the baseline operating conditions or switching to a new operating condition, the hydrogen flow rate of subsequent reaction sections is proportionally distributed according to the rate ratio. This ensures that the hydrogen supply to each reaction section matches the reactivity of that section, avoiding local under- or over-hydrogenation and guaranteeing the uniformity of the product structure. When adjusting the total flow rate or switching operating conditions, the rate ratio of each section remains constant, ensuring the kinetic balance of the entire reaction process and preventing an increase in side reactions due to sudden changes in flow rate. Only the hydrogen flow rate of the first section needs to be determined; the flow rates of subsequent sections are automatically calculated proportionally, simplifying control complexity and improving system response rate.

[0046] Example 3, based on Example 1 or 2, In step 4, the formaldehyde aqueous solution is added dropwise in several batches. During the experimental stage, the time-material temperature curve corresponding to the qualified step 4 is obtained, and the time period and drop rate of the formaldehyde aqueous solution are marked. A model is constructed that includes "the drop rate range of drop order 1, the reaction rate temperature factor range of drop order 1, and the ratio of the addition rate of the other drop orders to the actual drop rate of drop order 1". Before the first addition of formaldehyde aqueous solution, the material temperature in the reactor was 30℃; the reaction process temperature was between 30℃ and 35℃.

[0047] The actual production process is controlled based on the model, and step 4 specifically includes: Step 41: Add concentrated sulfuric acid to the reactor, and then adjust the temperature to 30°C; Step 42: At 30℃, begin adding formaldehyde aqueous solution at the minimum drop rate interval of drop sequence 1 for an initial duration (the initial duration refers to a fixed time window used to collect reaction data and calculate the actual reaction rate temperature factor after drop sequence 1 starts adding at the minimum rate interval. It can be taken as 1%–3% of the total duration of drop sequence 1, with a typical value of 30 seconds), and determine the actual rate of change of material temperature in the reactor corresponding to the initial duration, and determine the actual reaction rate temperature factor; If the actual reaction rate temperature factor meets the temperature factor range of the corresponding order, then continue to maintain the dropping acceleration rate to complete the dropping of dropping order 1; If the actual reaction rate temperature factor is greater than the upper limit of the temperature factor range of the corresponding sequence, an alarm will be triggered; this indicates that the reaction is exothermic too quickly and there is a risk of overheating. The system will immediately alarm to remind the operator to intervene and avoid safety or quality accidents.

[0048] If the actual reaction rate temperature factor is less than the lower limit of the temperature factor for the corresponding order, then increasing the dropping rate to satisfy the dropping order 1 indicates that the reaction is too slow and the efficiency is low. In this case, appropriately increasing the dropping rate within the rate range of order 1 can improve the reaction efficiency without exceeding the temperature limit, while ensuring that the reaction process remains within a controllable range. Specifically, determine the deviation rate between the actual reaction rate temperature factor and the lower limit of the temperature factor for the corresponding order; the deviation rate is: (lower limit of the temperature factor for the corresponding order - actual reaction rate temperature factor) ÷ actual reaction rate temperature factor. When the deviation rate is greater than 0 and less than or equal to 0.1, the dropping rate of dropping sequence 1 increases by 3%; When the deviation rate is greater than 0.1 and less than or equal to 0.25; the dropping rate of dropping sequence 1 increases by 5%; When the deviation rate is greater than 0.25 and less than or equal to 0.35, the rate of increase for drop addition sequence 1 is 7%. Maintain the new dropping rate for 10–30 seconds, and recalculate the actual reaction rate temperature factor and deviation rate. If the new factor falls within the normal range, maintain the rate to complete this sequence. If it is still below the lower limit, adjust it upwards again according to the above rules. When the dropping rate reaches the upper limit of the current sequence rate range, stop adjusting and issue an alarm regardless of the deviation rate, reminding manual intervention and initiating deviation analysis to investigate abnormal causes such as raw materials or temperature control system issues.

[0049] Reaction rate temperature factor = ; The temperature change rate is in °C / min; the reference temperature is 1 °C; the formaldehyde aqueous solution drop acceleration rate is in mL / min; the reference drop acceleration rate is 1 mL / min.

[0050] Step 43: If no alarm is triggered in step 42, the drip acceleration rate for the remaining dripping sequences is determined based on the final drip acceleration rate of sequence 1. Specifically, if no alarm is triggered in step 42, the final stable drip acceleration rate of sequence 1 is obtained as the reference rate; the drip acceleration rate of sequence 2 = reference rate × corresponding value in the interval (1.0–1.2), and the drip acceleration rate of sequence 3 = reference rate × corresponding value in the interval (1.2–1.33); subsequent sequences are still dynamically adjusted according to the deviation rate rule of sequence 1.

[0051] 1. Typical classifications are as follows: Sequence 1: Rate range of 0.1–0.15 mL / min, drop volume of 1 / 3 of the total formaldehyde aqueous solution drop volume; reaction rate temperature factor range of 0.8–1.2; Order 2: The ratio of the rate to the actual rate in rate interval 1 is 1.0–1.2, and the amount added is 1 / 3 of the total amount of formaldehyde aqueous solution added; Order 3: The ratio of the rate to the actual rate in rate interval 1 is 1.2–1.33, and the amount added is 1 / 3 of the total amount of formaldehyde aqueous solution added.

[0052] 2. First, multiple parallel experiments were conducted, each using a different dropping sequence (dropping volume for each sequence = total amount of formaldehyde aqueous solution dropped ÷ total number of corresponding sequences), dropping rate, and temperature control conditions. After each experiment, the purity, yield, and impurity content of the obtained product were tested, and process parameters such as temperature changes and dropping status were recorded. Batches whose product purity, yield, and impurity content all met the preset requirements, and whose reaction process exhibited stable temperature, no abnormal fluctuations, and no safety risks, were considered preliminarily qualified batches. Based on the process parameters corresponding to the preliminarily qualified batches, parameters such as the dropping rate were further fine-tuned, and repeated verification experiments were conducted to confirm that the results of multiple batches were consistently stable. Finally, batches with multiple consecutive batches of qualified product quality and stable and controllable reaction processes were determined as qualified batches, and the actual operating parameters of these qualified batches were used as the basis for determining subsequent process control parameters.

[0053] 2. In step 4 of the qualified batch, the material temperature and corresponding time in the reactor are continuously collected at a fixed frequency. Simultaneously, the start and end times and real-time dropping rate of each dropping sequence are recorded. A time-material temperature curve is plotted with time on the horizontal axis and temperature on the vertical axis for the qualified batch, and each dropping period and corresponding dropping rate interval is marked on the curve. The actual dropping rate range for each sequence is extracted from the records of the qualified batch. Based on multiple qualified batches of data, dropping rate interval requirements for each sequence are established. The first sequence must start from the lower limit of the interval, and the initial rate of subsequent sequences can be adjusted within the interval according to the reaction state of the previous sequence. For the real-time data of the qualified batch, the reaction rate temperature factor for sequence 1 is calculated based on the temperature change rate, dropping rate, and reference temperature. The distribution range of this factor in the qualified batch is statistically analyzed.

[0054] The above-mentioned dropping sequence, dropping rate range of sequence 1, ratio range of other sequences to dropping rate of sequence 1, and reaction rate temperature factor range of sequence 1 extracted from qualified batches are integrated into the control requirements of "qualified step 4".

[0055] Each batch can first undergo the above process, and then the final parameters of the first process can be controlled again. This method achieves precise matching between formaldehyde dropping and reaction heat through multi-parameter synergistic optimization. The beneficial effects of the above scheme are as follows: By constructing a control model that includes "the dropping acceleration rate range of the first dropping sequence, the reaction rate temperature factor range, and the rate ratio of subsequent sequences," the fine-grained control of the formaldehyde aqueous solution dropping process was achieved. This avoided the problems of incomplete reaction or aggravated side reactions caused by improper dropping acceleration, and significantly improved the stability of product quality.

[0056] The initial dropping sequence starts from the minimum rate range. Reaction data is collected based on the initial duration, and the actual reaction rate-temperature factor is calculated. This data is then used to dynamically adjust the initial dropping rate of subsequent sequences. This effectively adapts to subtle differences in the activity and concentration of raw materials from different batches, ensuring the consistency and controllability of the reaction process. When the reaction is too slow, the dropping rate is increased in stages based on the deviation rate, effectively improving reaction efficiency without exceeding the temperature limit. When the reaction is too exothermic, the system immediately alarms and prompts manual intervention, avoiding the risk of exceeding the temperature limit and achieving dual protection of production efficiency and process safety. By correlating the dropping rate of subsequent sequences with the actual rate of sequence 1, the control logic for multiple dropping sequences is simplified, system response delay is reduced, and iterative optimization of subsequent process parameters is facilitated, improving the overall operability and maintainability of the process.

[0057] Example 4: Based on any one of Examples 1-3, a method for preparing a highly insecticidal diamide compound yields an insecticidal diamide compound of N-(2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-(N-methyl-4-fluoro-3-chlorobenzamide)benzamide, which is used to control crop pests, including thrips. Experiment title: Field efficacy trial of chemical control of rose thrips; Experimental objective: To determine the field control efficacy of the tested pesticide against rose thrips and to test its safety in roses; Trial schedule: Trial start date: November 6, 2024; Trial application date: November 6, 2024; Trial investigation dates: November 7, 2024 (1 day after application), November 9, 2024 (3 days after application), November 13, 2024 (7 days after application); Trial end date: November 13, 2024. Test reagents: G42 is the diamide compound with high insecticidal activity of the present invention; G41, G43, G44, and 2% bromfenac diamide are all existing reagents provided by Shandong Huasheng New Materials Co., Ltd.; CK is the blank control area. Experimental target: Thrips; Experimental crop: Rose, of variety Elsa; Environmental conditions: The experimental site was a cold greenhouse, covering an area of ​​approximately 1.5 acres, all planted with roses. The surrounding area was also a rose cold greenhouse. During the experiment, the external temperature of the experimental site remained between 10℃ and 22℃, but the temperature inside the cold greenhouse was consistently maintained at around 23℃. The greenhouse was equipped with thermometers and drip irrigation devices, and the greenhouse film could be raised and lowered at any time to adjust the temperature and humidity. Throughout the experiment, the experimental site was in a relatively stable environment, with no extreme weather or temperature events. The number of roses planted in the experimental site was approximately 1500 plants per acre. The roses were in the flowering period when the pesticide was applied, with a row spacing of 20 cm and good growth. Normal water management was implemented during the experiment. Application equipment: SX-MD16H electric sprayer (Zhongbao Lvnong Technology Group), conical single nozzle, pressure 2.4Mpa, flow rate 1.2L / Min, 5ml syringe, 20ml syringe, 2000ml and 5000ml plastic graduated cylinders and ground pointers, plastic measuring cups, electronic scale, water bucket, measuring tape, marker pen and other test equipment; Application method: On November 6, 2024, dilute the pesticide with water to form a solution for spraying. Prepare the solution immediately before use. Prepare the irrigation water for the medium and use conventional foliar spraying. Conduct a water volume test in advance. The application should end when the rose leaves and flowers are dripping with water. Application timing and frequency: The application was carried out on November 6, 2024. The roses were in the flowering period at the time of application. Immediately after application, the flowers were bagged. Ten bags were used in each plot. Five bags were collected one day and three days after application for investigation. The number of dead and live thrips in the bags in each plot was observed and counted. The mortality rate and control effect were calculated. Seven days after application, five flowers were randomly collected from each plot, and the number of live thrips was recorded to calculate the seedling protection effect. The application dates and weather conditions are shown in Table 1 below: Table 1

[0058] As shown in Table 1, no severe weather conditions that would have affected the experiment occurred during the test period.

[0059] The following table shows the statistical results of the control efficacy of different agents against thrips: Statistical table of test results for the control of thrips with the tested pesticides (1 day after application)

[0060] Statistical table of test results for controlling thrips with the tested pesticides (3 days after application)

[0061] Statistical table of test results for controlling thrips with the tested pesticides (7 days after application)

[0062] ; ; ; The control effects of the tested agents on thrips are shown in Table 2 below: Table 2

[0063] The working principle and beneficial effects of the above technical solution are as follows: As shown in Table 2, one day after application, treatment area 2 had the highest thrips mortality rate and the best control efficacy, reaching 87.26%, significantly better than other treatments. Treatment areas 3 and 4 had the lowest thrips mortality rates, with control efficiencies of only 31.93% and 36.50%, respectively, significantly lower than other treatments. Three days after application, treatment areas 1 and 2 had relatively high thrips mortality rates, with control efficiencies both above 80%, showing excellent results and significantly better than other treatments. Treatment area 3 had control efficiencies of 65.01% and 74.72%, respectively. Treatment area 4 had the worst thrips mortality rate, with a control efficacy of only 33.12%. Seven days after application, treatment area 2 showed excellent efficacy against thrips, with only a small number of thrips surviving in the plot, and a long-lasting effect. Other treatments showed a large number of thrips. The efficacy of 2% G42 against rose thrips was relatively poor, with a short duration of action. Treatments 1 and 3 showed comparable efficacy to the control treatment 5. Treatment 4 had the worst efficacy against thrips, with only 24.55% efficacy. All tested pesticides had no significant adverse effects on roses and were safe for roses. In this experiment, pesticide 2% G42 showed excellent efficacy against rose thrips, with rapid death, good fast-acting properties, and a long duration of action. Pesticide 2% G41 showed good early-stage death of rose thrips, but its duration of action was short. Pesticides 2% G43 and 2% G44 showed poor efficacy against rose thrips and were not recommended for use. It is recommended to use pesticide 2% G42 (at a 300-fold dilution) during the rose flowering period, which has excellent efficacy against rose thrips and is safe for roses. Its efficacy is significantly better than that of the known control pesticide bromufen dimethyl dimethicone.

[0064] Obviously, those skilled in the art can make various modifications and variations to this invention without departing from its spirit and scope. Therefore, if these modifications and variations fall within the scope of the claims of this invention and their equivalents, this invention also intends to include these modifications and variations.

Claims

1. A method for preparing a diamide compound with high insecticidal activity, characterized in that: include: Step 1: Add 2-fluoro-3-nitrobenzoic acid, thionyl chloride and dimethylformamide sequentially to the reactor, then heat the reaction, remove thionyl chloride under reduced pressure to obtain acyl chloride, add dichloroethane to dissolve, and obtain a dichloroethane solution containing compound A; Step 2: Add sodium bicarbonate and 2-trifluoromethyl-4-heptafluoroisopropyl-6-bromoaniline to the material obtained in Step 1, then heat the mixture to react. After the reaction is complete, cool the mixture and add water to wash the product. Separate the liquid and evaporate the organic phase to dryness to obtain compound B. Step 3: Add compound B obtained in step 2 into the reactor, then add anhydrous ethanol and 5% palladium on carbon in sequence, and detect the concentration of compound B. Then replace the gas in the reactor. After the reaction is completed under a hydrogen atmosphere, filter and evaporate to obtain compound C. During the reaction under a hydrogen atmosphere, the reaction temperature and the hydrogen addition flow rate in each hydrogenation reaction section are determined based on the concentration of compound B. Step 4: Add concentrated sulfuric acid to the reactor, then control the temperature and add formaldehyde aqueous solution. After the reaction is completed, cool down and pour the reaction solution into ice water. After the solid precipitates, filter and wash with water. Dry the washed solid to obtain compound D. Step 5: Add toluene, 3-chloro-4-fluorobenzoic acid, thionyl chloride and dimethylformamide back into the reactor in sequence, heat and maintain the temperature until all are dissolved, and after the reaction is completed, remove the toluene solution containing compound E by vacuum distillation. Step 6: Add compound D to the material obtained in step 5, then heat the mixture to react. After the reaction is complete, pour the reaction solution into ice water, the solid precipitates out and is filtered and washed to obtain a diamide compound with high insecticidal activity.

2. The method for preparing a diamide compound with high insecticidal activity according to claim 1, characterized in that: The weight ratio of anhydrous ethanol, 5% palladium on carbon, and thionyl chloride added to the reactor in step 3 is 200:1:

100.

3. The method for preparing a diamide compound with high insecticidal activity according to claim 1, characterized in that: For different concentration ranges of compound B, the baseline parameter set corresponding to qualified production was determined by combining experimental calibration with historical production data. The baseline parameter set includes: the baseline hydrogen consumption rate ratio range for each hydrogenation reaction section, and the baseline average hydrogen consumption rate range for a set time period under different pressure and temperature groups. The pattern of "baseline average hydrogen consumption rate - baseline hydrogen injection flow rate" for the hydrogenation reaction zone corresponding to the set time period is defined; all temperature values ​​in the pressure and temperature group are within the range of 30℃ to 35℃. In step 3: Step 31: Add compound B obtained in step 2 into the reactor, then add anhydrous ethanol and 5% palladium on carbon in sequence, and detect the concentration of compound B; Step 32: Replace the gas in the reactor; Step 33: Control the hydrogen pressure to 0.3 MPa and the reaction temperature to 30°C to start the hydrogen addition reaction. Determine the actual average hydrogen consumption rate for the current set time period and compare it with the benchmark average hydrogen consumption rate range of [30°C, 0.3 MPa] to determine the rate deviation value. Based on the rate deviation, determine the corrected pressure and temperature group and the required hydrogen addition flow rate according to the correction strategy. Step 34: Based on the corrected pressure and temperature set and the required hydrogen addition flow rate determined in Step 33, continue the hydrogenation reaction.

4. The method for preparing a diamide compound with high insecticidal activity according to claim 3, characterized in that: The pressure and temperature groups include: [30℃, 0.3 MPa], [31℃, 0.3 MPa], [32℃, 0.3 MPa], [33℃, 0.3 MPa], [34℃, 0.3 MPa], [35℃, 0.3 MPa].

5. The method for preparing a diamide compound with high insecticidal activity according to claim 3, characterized in that: In step 33: Rate deviation value = (actual average hydrogen consumption rate - V) ÷ V; Among them, the half-width of the baseline average hydrogen consumption rate interval [30℃, 0.3MPa] is determined and denoted as B; And determine the comparison ratio of the median of the baseline average hydrogen consumption rate interval for other pressure and temperature groups to V; The median of the baseline average hydrogen consumption rate range [30℃, 0.3 MPa] is denoted as V; If the rate deviation is less than or equal to B / V, the corrected pressure and temperature group remains at [30℃, 0.3MPa]. The required hydrogen addition flow rate for the first hydrogenation reaction section is determined based on the actual average hydrogen consumption rate and the aforementioned pattern during the current set time period in step 33. If the rate deviation value is greater than B / V, an alarm will be triggered; If the rate deviation value is less than -B / V, the pressure and temperature group with a control ratio >1 and matching the rate deviation value is selected as the correction pressure and temperature group; and the required hydrogen addition flow rate of the first hydrogenation reaction section is determined based on the actual average hydrogen consumption rate of the current set time period in step 33 and the aforementioned pattern. The required hydrogen injection flow rate for the remaining hydrogenation reaction sections is determined based on the required hydrogen injection flow rate for the first hydrogenation reaction section.

6. The method for preparing a diamide compound with high insecticidal activity according to claim 1, characterized in that: The structural formula of compound A is The structural formula of compound B is The structural formula of compound C is The structural formula of compound D is The structural formula of compound E is The structural formula of the diamide compound with high insecticidal activity of the present invention is as follows: .

7. The method for preparing a diamide compound with high insecticidal activity according to claim 1, characterized in that: In step 1, the weight ratio of 2-fluoro-3-nitrobenzoic acid, thionyl chloride, and dimethylformamide added to the reactor is 18.5:100:

1. The mixture is then heated to 80°C and reacted for 6 hours. The thionyl chloride is removed by vacuum distillation to obtain acyl chloride. The weight ratio of dichloroethane added to the acyl chloride is the same as that of thionyl chloride added to the reactor. In step 2, the weight ratio of sodium bicarbonate, 2-trifluoromethyl-4-heptafluoroisopropyl-6-bromoaniline, and thionyl chloride added to the reactor in step 1 is 12.7:40.8:

100. After reacting at 70°C for 8 hours, the weight ratio of water added to the dichloroethane solution containing compound A and sodium bicarbonate added to the solution is 50:12.

7.

8. The method for preparing a diamide compound with high insecticidal activity according to claim 1, characterized in that: In step 4, the weight ratio of concentrated sulfuric acid added to the reactor to thionyl chloride added to the reactor in step 1 is 150:

100. The temperature is controlled at 30℃-35℃. The weight ratio of formaldehyde aqueous solution added to the reactor to concentrated sulfuric acid is 12.96:

150. After the reaction is completed, the temperature is lowered to room temperature.

9. The method for preparing a diamide compound with high insecticidal activity according to claim 1, characterized in that: In step 5, the weight ratio of toluene, 3-chloro-4-fluorobenzoic acid, thionyl chloride, dimethylformamide, and thionyl chloride added to the reactor in step 1 is 90:15.3:11.4:0.0948:100, and the temperature is raised to 90℃ and the reaction is carried out for 6 hours. In step 6, compound D was added to the toluene solution containing compound E in three portions. The total weight ratio of compound D to thionyl chloride added to the reactor in step 1 was 45:

100. The mixture was then heated to 105°C and refluxed for 8 hours. After the reaction was completed, the reaction solution was gradually cooled to room temperature. The solid precipitated and was filtered and washed twice to obtain a white solid.

10. A diamide compound with high insecticidal activity prepared by the method of any one of claims 1-9, which is used to control crop pests, wherein the pest is thrips.

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