Halogenated alkyl bisamide compound and application thereof

Abstract

The invention relates to the technical field of pesticide chemicals, in particular to a halogenated alkyl bisamide compound and application thereof. The structural formula of the halogenated alkyl bisamide compound synthesized by the invention is shown in the specification. According to the invention, a m-diamide structure is taken as a parent body, and the fat solubility of the bisamide compound is increased by introducing trifluoroethyl to an amide group, so that the bisamide compound can enter the interior of an insect body through a biological membrane more easily; and trifluoroethyl enhances the binding force between the bisamide molecule and target protein, so that the bisamide molecule shows better insecticidal activity.

Description

Technical Field

[0001] This invention relates to the technical field of pesticide chemicals, specifically to a haloalkyl diamide compound and its applications. Background Technology

[0002] γ-Aminobutyric acid, abbreviated as GABA, is released from synaptic cells during normal physiological processes. It binds to GABA receptors in insects, activating chloride ion channels and causing an influx of chloride ions, thereby inhibiting the insect's neural activity.

[0003] Metadiamide insecticides, as allosteric inhibitors of GABA-gated chloride channels, bind to the allosteric sites of these channels, causing conformational changes that prevent normal channel opening and thus blocking chloride ion influx. Disruption of this inhibition leads to persistent hyperexcitability of the insect's nervous system, ultimately resulting in spasms and death. Brofenoxam is a representative commercial product with this mechanism of action. Developed jointly by Mitsui Chemicals and BASF, it was reclassified as a new category, Group 30, by the International Pesticide Resistance Action Committee in 2017. This product demonstrates good control efficacy against lepidopteran pests (such as beet armyworm and diamondback moth), coleopteran pests (such as flea beetles), and tsunamipteran pests (such as thrips). The structural formula of brofenoxam is as follows:

[0004] .

[0005] However, in practical applications, existing m-diamide compounds usually require higher dosages to achieve sufficient field efficacy, which not only increases the cost of application but also easily induces plant damage and resistance. Summary of the Invention

[0006] To address the technical problem that existing m-diamid compounds require increased dosage to achieve sufficient field efficacy, which not only increases application costs but also easily induces phytotoxicity and resistance in plants, this invention provides a haloalkyl diamide compound and its application. This invention increases the lipid solubility of the diamide compound by introducing a fluorinated ethyl group onto the amide group, making it easier to penetrate biomembranes and enter the insect's body. Furthermore, the fluorinated ethyl group enhances the binding force between the diamide molecule and the target protein, acting as an allosteric inhibitor of GABA-gated chloride ion channels, inducing pest death and exhibiting better insecticidal activity. Superior insecticidal rates can be achieved at equal or lower application doses.

[0007] The first objective of this invention is to provide a haloalkyl diamide compound, the chemical structural formula of which is as follows: ; In the formula, X is selected from ketone or sulfonyl groups; R 1 Selected from substituted phenyl, substituted pyridine ring, or substituted C5 heteroaryl; R 2 Selected from trifluoromethyl, difluoromethyl, or monofluoromethyl; R 3 Selected from halogens or methyl groups.

[0008] Preferred, R 1 The substituents are selected from at least one of halogen, nitro, cyano, methanesulfonyl, methoxy, and C1-C4 alkyl and C1-C4 haloalkyl.

[0009] Preferably, the heteroatom of the C5 heteroaryl group is selected from at least one of N, O and S.

[0010] Preferably, the haloalkyl diamide compound is selected from one of the following compounds: , , , , , , , , , , , , , , , , , , , , .

[0011] Preferably, the haloalkyl diamide compound is selected from one of the following compounds: , , , , , , , , , , , , .

[0012] The second objective of this invention is to provide the application of haloalkyl diamide compounds in the preparation of pesticides for controlling pests.

[0013] Preferably, haloalkyl diamide compounds are used in the preparation of pesticides for controlling pests, and other small molecule pesticides or biological pesticides are used before, after or simultaneously with the use of haloalkyl diamide compounds.

[0014] Preferably, when used, the concentration of haloalkyl diamide compounds in pesticides for controlling pests is 10 ppm to 100 ppm.

[0015] Preferably, the pest is an insect containing a γ-aminobutyric acid receptor.

[0016] Preferred insects containing γ-aminobutyric acid (GABA) receptors include at least one of the following: diamondback moth, beet armyworm, fall armyworm, cabbage caterpillar, bean pod borer, bean hawk moth, kapok worm, cutworm, bean armyworm, forked armyworm, cabbage armyworm, peach leafminer, grape berry leafroller, beet webworm, spiral leafminer, coffee leafminer, tomato moth, apple leafminer, peach leafminer, wax moth, plum fruit moth, pear fruit moth, corn borer, tobacco leafminer, corn ear worm, apple leafroller, fall webworm, citrus leafminer, potato leafminer, soybean leafminer, diamondback moth, wheat moth, grape leafroller, jasmine bud borer, sea gray-winged moth, white-winged moth, armyworm, rice stem borer, three-spined rice stem borer, and scale insects.

[0017] Preferably, the insects containing γ-aminobutyric acid (GABA) receptors are the beet armyworm or the rice stem borer. At the same test concentration, the compounds of the present invention exhibit higher lethality against both the beet armyworm and the rice stem borer. At concentrations that effectively control pests, they demonstrate superior safety to test crops, significantly reducing the incidence of phytotoxicity symptoms and helping to broaden their application scope.

[0018] Compared with the prior art, the present invention has the following technical effects: This invention uses a m-diamid structure as the parent compound and increases the lipophilicity of the diamide compound by introducing a trifluoroethyl group onto the amide group, making it easier for it to penetrate the insect's body through biomembranes. Furthermore, the trifluoroethyl group enhances the binding force between the diamide molecule and the target protein, acting as an allosteric inhibitor of GABA-gated chloride ion channels, inducing insect death and thus exhibiting better insecticidal activity. It achieves superior insecticidal rates at equal or lower application doses. This invention solves the technical problem of existing m-diamid compounds requiring higher dosages to achieve sufficient field efficacy, which not only increases application costs but also easily induces phytotoxicity and resistance in plants.

[0019] This invention utilizes fragment-based drug molecule design, synthesis, and activity screening techniques to discover a series of promising lead compounds. These compounds exhibit high biological activity, thus requiring lower drug dosages, making them safer and more environmentally friendly. Attached Figure Description

[0020] Figure 1 This is the chemical structural formula of the haloalkyl diamide compounds synthesized in this invention.

[0021] Figure 2 The NMR spectrum data of compound XL01 synthesized in Example 1 are shown.

[0022] Figure 3 The NMR spectrum data of compound XL02 synthesized in Example 2 are shown.

[0023] Figure 4 The NMR spectrum data of compound XL03 synthesized in Example 3 are shown.

[0024] Figure 5 The NMR spectrum data of compound XL04 synthesized in Example 4 are shown.

[0025] Figure 6 The NMR spectrum data of compound XL06 synthesized in Example 6 are shown.

[0026] Figure 7 The NMR spectrum data are for compound XL07 synthesized in Example 7.

[0027] Figure 8 The NMR spectrum data of compound XL08 synthesized in Example 8 are shown.

[0028] Figure 9 The NMR spectrum data of compound XL10 synthesized in Example 10 are shown.

[0029] Figure 10 The NMR spectrum data of compound XL11 synthesized in Example 11 are shown.

[0030] Figure 11 The NMR spectrum data of compound XL12 synthesized in Example 12 are shown.

[0031] Figure 12 The NMR spectrum data of compound XL13 synthesized in Example 13 are shown. Detailed Implementation

[0032] To enable those skilled in the art to better understand and implement the technical solutions of the present invention, the present invention will be further described below in conjunction with specific embodiments.

[0033] Unless otherwise specified, all reagents used in this invention are commercially available, and all methods used are conventional techniques in the art.

[0034] It should be noted that the specific synthetic routes for the intermediate compounds XL01-02, XL01-03, XL01-04, and XL01-05 required in the synthesis of haloalkyl diamides are as follows: .

[0035] Step 1, Synthesis of compound XL01-02: At room temperature, 4-(perfluoropropane-2-yl)-2-trifluoromethylaniline (MW=329, 253.43 g, 0.77 mol) and potassium iodide (MW=166, 76.70 g, 0.462 mol) as shown in formula XL01-01 were dispersed in acetonitrile (350 mL) and heated to reflux. 3-nitro-2-methylbenzoyl chloride (MW=200, 200 g, 1.00 mol) was added in portions, and the reaction was carried out at 80 °C. The reaction process was monitored by liquid chromatography. When the content of 4-(perfluoropropane-2-yl)-2-trifluoromethylaniline (formula XL01-01) was less than 1%, the mixture was cooled to room temperature, acetonitrile was concentrated, and the mixture was hot-beaten twice with sodium carbonate aqueous solution (0.5 mol / L, 300 mL). After cooling to room temperature, the mixture was filtered, and the filter cake was dried at 60 °C to obtain compound XL01-02 (MW = 492, 341 g), with a yield of 90%. The mass spectrometry data of compound XL01-02 were: MS (ESI, m / z): 493.00 [M+H] + .

[0036] Step 2, Synthesis of compound XL01-03: Compound XL01-02 (MW=492, 49.20 g, 0.10 mol) and N-bromosuccinimide (MW=178, 26.70 g, 0.15 mol) were dispersed in acetonitrile (50 mL) at room temperature. Pyridine (MW=79, 15.80 g, 0.20 mol) was added, and the mixture was heated to 80 °C. The reaction process was monitored by liquid chromatography. When the content of compound XL01-02 was less than 1%, the mixture was cooled to room temperature, and the acetonitrile was concentrated. The mixture was slurried once with 5% sodium hydroxide aqueous solution (100 g), filtered, and then slurried once with 5% hydrochloric acid aqueous solution (100 g), filtered, and the filter cake was dried at 60 °C to obtain compound XL01-03 (MW=570, 50.11 g), with a yield of 88%. The mass spectrometry data of compound XL01-03 are as follows: MS (ESI, m / z): 570.90 [M+H] + .

[0037] Step 3, Synthesis of compound XL01-04: At room temperature, compound XL01-03 (MW=570, 57.00g, 0.10mol) was dispersed in 95% ethanol (300g), concentrated hydrochloric acid (12mol / L, 30g, 0.36mol) and acetic acid (MW=60, 12.00g, 0.20mol) were added, and iron powder (MW=56, 20g, 0.35mol) was slowly added. After the reaction stabilized, the temperature was raised to 80℃ for further reaction. The reaction process was monitored by liquid chromatography. When the content of compound XL01-03 was below 1%, the mixture was cooled to room temperature. The pH of the reaction solution was adjusted to 10–12 with a 10% sodium hydroxide aqueous solution. The mixture was filtered through diatomaceous earth, and the filtrate was concentrated to remove ethanol. The residue was extracted twice with dichloromethane (200 g). The dichloromethane phase was dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to obtain compound XL01-04 (MW = 540, 46.20 g), with a yield of 85%. The mass spectrometry data of compound XL01-04 were: MS (ESI, m / z): 540.90 [M+H] + .

[0038] Step 4, Synthesis of compound XL01-05: Compound XL01-04 (MW=540, 54.00 g, 0.10 mol), trifluoroethyl trifluoromethanesulfonate (MW=232, 46.46 g, 0.20 mol), and trisodium phosphate (MW=164, 32.79 g, 0.20 mol) were dispersed in N,N-dimethylformamide (150 g) at room temperature and the mixture was heated to 80 °C. The reaction was monitored by liquid chromatography. When the content of compound XL01-04 was less than 1%, the mixture was cooled to room temperature, and water (400 g) was added. The mixture was then extracted twice with dichloromethane (200 g). The dichloromethane phase was washed twice with 5% sodium hydroxide aqueous solution (100 g) and twice with water (100 g), dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to obtain compound XL01-05 (MW=622, 59.12 g), with a yield of 95%. The mass spectrometry data of compound XL01-05 are as follows: MS (ESI, m / z): 622.90 [M+H] + .

[0039] Alternatively, at room temperature, compound XL01-04 (MW=540, 54.00 g, 0.10 mol), trifluoroethyl benzenesulfonate (MW=240, 28.80 g, 0.12 mol), and potassium carbonate (MW=138, 27.60 g, 0.20 mol) were dispersed in N,N-dimethylformamide (150 g), and the mixture was heated to 80 °C. The reaction was monitored by liquid chromatography. When the content of compound XL01-04 was less than 1%, the mixture was cooled to room temperature, and water (400 g) was added. The mixture was extracted twice with dichloromethane (200 g). The dichloromethane phase was washed twice with 5% sodium hydroxide aqueous solution (100 g) and twice with water (100 g), dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to obtain compound XL01-05 (MW=622, 54.74 g), with a yield of 88%.

[0040] Alternatively, at room temperature, XL01-04 (MW=540, 54.00 g, 0.10 mol), trifluoroethyl p-toluenesulfonate (MW=254, 30.48 g, 0.12 mol), and trisodium phosphate (MW=164, 32.79 g, 0.20 mol) were dispersed in N,N-dimethylformamide (150 g), and the mixture was heated to 80 °C for reaction. The reaction process was monitored by liquid chromatography. When the content of compound XL01-04 was less than 1%, the mixture was cooled to room temperature, water (400 g) was added, and the mixture was extracted with dichloromethane (200 g × 2). The dichloromethane phase was washed with 5% sodium hydroxide aqueous solution (100 g × 2) and water (100 g × 2), respectively. The mixture was dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to obtain compound XL01-05 (MW=622, 52.87 g), with a yield of 85%.

[0041] The synthetic route for the intermediate compound XL03-02, required in the synthesis of haloalkyl diamides, is shown below: .

[0042] Compound XL03-01 (MW=544, 54.40 g, 0.10 mol), trifluoroethyl trifluoromethanesulfonate (MW=232, 46.46 g, 0.20 mol), and trisodium phosphate (MW=164, 32.79 g, 0.20 mol) were dispersed in N,N-dimethylformamide (150 g) at room temperature, and the reaction was heated to 80 °C. The reaction process was monitored by liquid chromatography. When the content of compound XL03-01 was less than 1%, the mixture was cooled to room temperature, and water (400 g) was added. The mixture was extracted with dichloromethane (200 g × 2). The dichloromethane phase was washed with 5% sodium hydroxide aqueous solution (100 g × 2) and water (100 g × 2), respectively. The mixture was dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to obtain compound XL03-02 (MW=626, 53.84 g), with a yield of 86%. The mass spectrometry data for compound XL03-02 are as follows: MS (ESI, m / z): 626.90 [M+H] + .

[0043] The synthetic routes for the intermediate compounds XL10-02 and XL10-03 required in the synthesis of haloalkyl diamides are shown below: .

[0044] Step 1, Synthesis of compound XL10-02: At room temperature, compound XL10-01 (MW=82, 82.00 g, 1.00 mol) and triethylamine (MW=101, 111.10 g, 1.10 mol) were dissolved in dichloromethane (500 g), and benzenesulfonyl chloride (MW=176, 167.20 g, 0.95 mol) was slowly added dropwise. The reaction process was monitored by liquid chromatography. When the content of benzenesulfonyl chloride (n-propylamine derivative) was less than 1%, the mixture was filtered. The dichloromethane phase was washed with 5% hydrochloric acid aqueous solution (100 g × 2) and water (100 g × 2), dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give compound XL10-02 (MW=222, 201.00 g), with a yield of 95%.

[0045] Step 2, Synthesis of compound XL10-03: Compounds XL03-01 (MW=544, 54.40 g, 0.10 mol), XL10-02 (MW=222, 33.30 g, 0.15 mol), and trisodium phosphate (MW=164, 32.79 g, 0.20 mol) were dispersed in N,N-dimethylformamide (150 g) at room temperature and the reaction was heated to 80 °C. The reaction process was monitored by liquid chromatography. When the content of compound XL03-01 was less than 1%, the mixture was cooled to room temperature, and water (400 g) was added. The mixture was extracted with dichloromethane (200 g × 2). The dichloromethane phase was washed with 5% sodium hydroxide aqueous solution (100 g × 2) and water (100 g × 2), respectively. The mixture was dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to obtain compound XL10-03 (MW=608, 54.64 g), with a yield of 90%. The mass spectrometry data for compound XL10-03 are as follows: MS (ESI, m / z): 608.90 [M+H] + .

[0046] In a specific example of the synthesis of haloalkyl diamide compounds, the synthetic routes for the required intermediate compounds XL12-02 and XL12-03 are shown below: .

[0047] Step 1, Synthesis of compound XL12-02: At room temperature, compound XL12-01 (MW=64, 64.00 g, 1.00 mol) and triethylamine (MW=101, 111.10 g, 1.10 mol) were dissolved in dichloromethane (500 g), and benzenesulfonyl chloride (MW=176, 167.20 g, 0.95 mol) was slowly added dropwise. The reaction process was monitored by liquid chromatography. When the content of benzenesulfonyl chloride (n-propylamine derivative) was less than 1%, the mixture was filtered. The dichloromethane phase was washed with 5% hydrochloric acid aqueous solution (100 g × 2) and water (100 g × 2), dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give compound XL12-02 (MW=204, 186.00 g), with a yield of 91%.

[0048] Step 2, Synthesis of compound XL12-03: Compounds XL03-01 (MW=544, 54.40 g, 0.10 mol), XL12-02 (MW=204, 30.60 g, 0.15 mol), and trisodium phosphate (MW=164, 32.79 g, 0.20 mol) were dispersed in N,N-dimethylformamide (150 g) at room temperature and the reaction was heated to 80 °C. The reaction process was monitored by liquid chromatography. When the content of compound XL03-01 was less than 1%, the mixture was cooled to room temperature, and water (400 g) was added. The mixture was extracted with dichloromethane (200 g × 2). The dichloromethane phase was washed with 5% sodium hydroxide aqueous solution (100 g × 2) and water (100 g × 2), respectively. The mixture was dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to obtain compound XL12-03 (MW=590, 50.43 g), with a yield of 85%. The mass spectrometry data for compound XL12-03 are as follows: MS (ESI, m / z): 590.90 [M+H] + .

[0049] Example 1 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0050] Compound XL01-05 (MW=622, 62.20 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The temperature was lowered to 0℃~5℃, and p-fluorobenzoyl chloride (MW=158, 16.59 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL01-05 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), dried, and the crude product was recrystallized from anhydrous ethanol to obtain compound XL01 (MW=744, 40.92 g), with a yield of 55%.

[0051] like Figure 2 The mass spectrometry data for compound XL01 are shown below: MS (ESI, m / z): 744.90 [M+H] + The 1H NMR data are as follows: 1H NMR (400 MHz, DMSO) δ 10.07 (s, 1H), 8.12 (s, 1H), 8.11 - 8.00 (m, 2H), 7.81 (s, 1H), 7.44 (d, J = 7.9 Hz, 1H), 7.37 (t, J = 8.1 Hz, 2H), 7.13 (t, J = 7.7 Hz, 1H), 6.84 (d, J = 7.7 Hz, 1H), 5.29 - 5.05 (m, 2H), 2.36 (s, 3H).

[0052] Example 2 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0053] Compound XL01-05 (MW=622, 62.20 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The temperature was lowered to 0℃~5℃, and p-chlorobenzoyl chloride (MW=174, 19.14 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL01-05 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), respectively. The mixture was dried, and the crude product was recrystallized from anhydrous ethanol to obtain compound XL02 (MW=760, 47.12 g), with a yield of 62%.

[0054] like Figure 3 As shown, the mass spectrometry data for compound XL02 are: MS (ESI, m / z): 760.90 [M+H] + The 1H NMR data are as follows: 1H NMR (400 MHz, DMSO) δ 10.10 (s, 1H), 8.11 (s, 1H), 7.99 (d, J = 7.9 Hz, 2H), 7.80 (s, 1H), 7.60 (d, J = 8.0 Hz, 2H), 7.43 (d, J = 8.1 Hz, 1H), 7.12 (t, J = 7.5 Hz, 1H), 6.83 (d, J = 7.6 Hz, 1H), 5.13 (dt, J = 20.4, 10.5 Hz, 2H), 2.34 (s, 3H).

[0055] Example 3 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0056] Compound XL03-01 (MW=544, 54.40 g, 0.10 mol), trifluoroethyl trifluoromethanesulfonate (MW=232, 46.46 g, 0.20 mol), and trisodium phosphate (MW=164, 32.79 g, 0.20 mol) were dispersed in N,N-dimethylformamide (150 g) at room temperature, and the reaction was heated to 80 °C. The reaction process was monitored by liquid chromatography. When the content of compound XL03-01 was less than 1%, the mixture was cooled to room temperature, and water (400 g) was added. The mixture was extracted with dichloromethane (200 g × 2). The dichloromethane phase was washed with 5% sodium hydroxide aqueous solution (100 g × 2) and water (100 g × 2), respectively. The mixture was dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to obtain compound XL03-02 (MW=626, 53.84 g), with a yield of 86%. The mass spectrometry data for compound XL03-02 are as follows: MS (ESI, m / z): 626.90 [M+H] + .

[0057] Compound XL03-02 (MW=626, 62.60 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The temperature was lowered to 0℃~5℃, and p-fluorobenzoyl chloride (MW=158, 16.59 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of XL03-02 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), dried, and the crude product was recrystallized from anhydrous ethanol to obtain compound XL03 (MW=748, 43.38 g), with a yield of 58%.

[0058] like Figure 4 As shown, the mass spectrometry data for compound XL03 are: MS (ESI, m / z): 748.90 [M+H] + The 1H NMR data are as follows: 1H NMR (400 MHz, DMSO) δ 10.26 (s, 1H), 8.12 (s, 1H), 8.07 - 7.96 (m, 2H), 7.79 (s, 1H), 7.73 (t, J = 7.2 Hz, 1H), 7.35 (t, J = 8.4 Hz, 2H), 7.18 (t, J = 7.7 Hz, 1H), 7.02 (d, J = 6.1 Hz, 1H), 5.29 - 5.06 (m, 2H).

[0059] Example 4 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0060] Compound XL03-02 (MW=626, 62.60 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The temperature was lowered to 0℃~5℃, and p-chlorobenzoyl chloride (MW=174, 19.14 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL03-02 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), respectively. The mixture was dried, and the crude product was recrystallized from anhydrous ethanol to obtain compound XL04 (MW=764, 45.23 g), with a yield of 59%.

[0061] like Figure 5 As shown, the mass spectrometry data for compound XL04 are: MS (ESI, m / z): 764.90 [M+H] + The 1H NMR data are as follows: 1 H NMR (400 MHz, DMSO) δ 10.33 (s, 1H), 8.11 (s, 1H), 7.95 (d, J =8.0 Hz, 2H), 7.75 (dd, J = 16.2, 8.8 Hz, 2H), 7.59 (d, J = 8.0 Hz, 2H), 7.18 (t, J = 7.8 Hz, 1H), 7.01 (t, J = 6.4 Hz, 1H), 5.28 - 5.03 (m, 2H).

[0062] Example 5 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0063] Compound XL03-02 (MW=626, 62.60 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The mixture was cooled to 0℃~5℃, and p-cyanobenzoyl chloride (MW=165, 18.15 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of XL03-02 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was then filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), dried, and the crude product was recrystallized from anhydrous ethanol to give compound XL05 (MW=755, 47.83 g), with a yield of 63%. The mass spectrometry data for compound XL05 are as follows: MS (ESI, m / z): 755.90 [M+H] + .

[0064] Example 6 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0065] Compound XL03-02 (MW=626, 62.60 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The mixture was cooled to 0℃~5℃, and p-methoxybenzoyl chloride (MW=170, 18.70 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of XL03-02 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), respectively. The mixture was dried, and the crude product was recrystallized from anhydrous ethanol to give compound XL06 (MW=760, 36.69 g), with a yield of 48%.

[0066] like Figure 6 The mass spectrometry data for compound XL06 are shown below: MS (ESI, m / z): 760.90 [M+H] + The 1H NMR data are as follows: 1H NMR (400 MHz, DMSO) δ 10.05 (s, 1H), 8.12 (s, 1H), 7.92 (d, J =8.8 Hz, 2H), 7.79 (s, 1H), 7.71 (d, J = 7.3 Hz, 1H), 7.16 (t, J = 8.0 Hz,1H), 7.04 (d, J = 8.8 Hz, 2H), 6.99 (d, J = 6.3 Hz, 1H), 5.17 (t, J = 8.9 Hz,2H), 3.82 (s, 3H).

[0067] Example 7 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0068] Compound XL03-02 (MW=626, 62.60 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The mixture was cooled to 0℃~5℃, and p-methanesulfonylbenzoyl chloride (MW=218, 24.00 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of XL03-02 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was then filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), dried, and recrystallized from the crude product with anhydrous ethanol to obtain compound XL07 (MW=808, 47.88 g), with a yield of 59%.

[0069] like Figure 7 The mass spectrometry data for compound XL07 are shown below: MS (ESI, m / z): 808.90 [M+H] + The 1H NMR data are as follows: 1 H NMR (400 MHz, DMSO) δ 10.52 (s, 1H), 8.14 (d, J = 8.6 Hz, 3H), 8.07 (d, J = 8.2 Hz, 2H), 7.79 (d, J = 6.0 Hz, 2H), 7.19 (d, J = 8.0 Hz, 1H), 7.03 (s, 1H), 5.27 - 5.09 (m, 2H), 3.28 (s, 3H).

[0070] Example 8 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0071] Compound XL03-02 (MW=626, 62.60 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The temperature was lowered to 0℃~5℃, and p-nitrobenzoyl chloride (MW=185, 20.35 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL03-02 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), respectively. The mixture was dried, and the crude product was recrystallized from anhydrous ethanol to obtain compound XL08 (MW=775, 40.65 g), with a yield of 52%.

[0072] like Figure 8 As shown, the mass spectrometry data for compound XL08 are: MS (ESI, m / z): 775.90 [M+H] + The 1H NMR data are as follows: 1 H NMR (400 MHz, DMSO) δ 10.61 (s, 1H), 8.35 (d, J = 7.5 Hz, 2H), 8.20 - 8.06 (m, 3H), 7.77 (d, J = 9.3 Hz, 2H), 7.20 (t, J = 7.5 Hz, 1H), 7.03 (d, J = 6.0 Hz, 1H), 5.26 - 5.08 (m, 2H).

[0073] Example 9 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0074] Compound XL03-02 (MW=626, 62.60 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The temperature was lowered to 0℃~5℃, and p-fluorobenzenesulfonyl chloride (MW=194, 20.35 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL03-02 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), respectively. The mixture was dried, and the crude product was recrystallized from anhydrous ethanol to obtain compound XL08 (MW=784, 38.50 g), with a yield of 49%. The mass spectrometry data for compound XL09 are as follows: MS (ESI, m / z): 784.90 [M+H] + .

[0075] Example 10 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0076] Compound XL10-03 (MW=608, 60.80 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The temperature was lowered to 0℃~5℃, and p-fluorobenzoyl chloride (MW=158, 16.59 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL10-03 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), respectively. The mixture was dried, and the crude product was recrystallized from anhydrous ethanol to obtain compound XL10 (MW=730, 43.32 g), with a yield of 59%.

[0077] like Figure 9 The mass spectrometry data for compound XL10 are shown below: MS (ESI, m / z): 730.90 [M+H] + The 1H NMR data are as follows: 1H NMR (400 MHz, DMSO) δ 10.23 (s, 1H), 8.09 (s, 1H), 8.04 - 7.93 (m, 2H), 7.77 (s, 1H), 7.71 (dd, J = 11.0, 4.1 Hz, 1H), 7.41 - 7.29 (m, 2H), 7.18 (t, J = 7.9 Hz, 1H), 7.04 (dd, J = 9.9, 3.8 Hz, 1H), 6.46 (tt, J = 54.1, 3.1 Hz, 1H), 4.84 - 4.59 (m, 2H).

[0078] Example 11 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0079] Compound XL10-03 (MW=608, 60.80 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The temperature was lowered to 0℃~5℃, and p-chlorobenzoyl chloride (MW=174, 19.14 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL10-03 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), respectively. The mixture was dried, and the crude product was recrystallized from anhydrous ethanol to obtain compound XL11 (MW=746, 39.02 g), with a yield of 52%.

[0080] like Figure 10 The mass spectrometry data for compound XL11 are shown below: MS (ESI, m / z): 746.90 [M+H] + The 1H NMR data are as follows: 1H NMR (400 MHz, DMSO) δ 10.29 (s, 1H), 8.10 (s, 1H), 7.94 (d, J =8.6 Hz, 2H), 7.77 (s, 1H), 7.71 (t, J = 6.9 Hz, 1H), 7.60 (t, J = 5.6 Hz,2H), 7.18 (t, J = 7.9 Hz, 1H), 7.03 (t, J = 6.2 Hz, 1H), 6.64 - 6.29 (m, 1H), 4.81 - 4.62 (m, 2H).

[0081] Example 12 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0082] Compound XL12-03 (MW=590, 59.00 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The temperature was lowered to 0℃~5℃, and p-fluorobenzoyl chloride (MW=158, 16.59 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL12-03 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), respectively. The mixture was dried, and the crude product was recrystallized from anhydrous ethanol to give compound XL12 (MW=712, 36.26 g), with a yield of 51%.

[0083] like Figure 11 As shown, the mass spectrometry data for compound XL12 are: MS (ESI, m / z): 713.90 [M+H] + The 1H NMR data are as follows: 1H NMR (400 MHz, DMSO) δ 10.22 (s, 1H), 8.08 (s, 1H), 8.00 (dd, J =8.7, 5.5 Hz, 2H), 7.76 (s, 1H), 7.69 (t, J = 7.1 Hz, 1H), 7.35 (t, J = 8.8Hz, 2H), 7.16 (t, J = 7.9 Hz, 1H), 7.03 (t, J = 6.3 Hz, 1H), 4.92 - 4.82 (m,1H), 4.79 - 4.73 (m, 1H), 4.73 - 4.66 (m, 1H), 4.66 - 4.56 (m, 1H).

[0084] Example 13 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0085] Compound XL12-03 (MW=590, 59.00 g, 0.10 mol) and pyridine (MW=79, 15.80 g, 0.20 mol) were dispersed in dichloromethane (200 g) at room temperature. The temperature was lowered to 0℃~5℃, and p-chlorobenzoyl chloride (MW=174, 19.14 g, 0.11 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL12-03 was less than 1%, water (400 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (150 g × 2), 5% sodium hydroxide aqueous solution (150 g × 2), and water (150 g × 2), respectively. The mixture was dried, and the crude product was recrystallized from anhydrous ethanol to obtain compound XL13 (MW=728, 33.16 g), with a yield of 46%.

[0086] like Figure 12 The mass spectrometry data for compound XL13 are shown below: MS (ESI, m / z): 728.90 [M+H] + The 1H NMR data are as follows: 1H NMR (400 MHz, DMSO) δ 10.28 (s, 1H), 8.08 (s, 1H), 7.94 (d, J =8.6 Hz, 2H), 7.76 (s, 1H), 7.69 (t, J = 6.9 Hz, 1H), 7.59 (d, J = 8.6 Hz,2H), 7.16 (t, J = 7.9 Hz, 1H), 7.03 (t, J = 6.2 Hz, 1H), 4.87 (dt, J = 5.5,3.0 Hz, 1H), 4.79 - 4.73 (m, 1H), 4.73-4.65 (m, 1H), 4.65 - 4.57 (m, 1H).

[0087] Example 14 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0088] Compound XL03-02 (MW=626, 6.26 g, 0.01 mol) and pyridine (MW=79, 1.58 g, 0.02 mol) were dispersed in dichloromethane (20 g) at room temperature. The temperature was lowered to 0℃~5℃, and 3,4-difluorobenzoyl chloride (MW=176, 1.94 g, 0.011 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL03-02 was less than 1%, water (40 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (15 g × 2), 5% sodium hydroxide aqueous solution (15 g × 2), and water (15 g × 2). After drying, the crude product was recrystallized from anhydrous ethanol to obtain compound XL14 (MW=766, 3.92 g), with a yield of 51%. The mass spectrometry data for compound XL14 are as follows: MS (ESI, m / z): 766.90 [M+H] + .

[0089] Example 15 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0090] Compound XL03-02 (MW=626, 6.26 g, 0.01 mol) and pyridine (MW=79, 1.58 g, 0.02 mol) were dispersed in dichloromethane (20 g) at room temperature. The mixture was cooled to 0℃~5℃, and 6-chloronicotinyl chloride (MW=175, 1.74 g, 0.011 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL03-02 was less than 1%, water (40 g) was added to concentrate the dichloromethane. The mixture was then filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (15 g × 2), 5% sodium hydroxide aqueous solution (15 g × 2), and water (15 g × 2). After drying, the crude product was recrystallized from anhydrous ethanol to obtain compound XL15 (MW=765, 1.72 g), with a yield of 22%. The mass spectrometry data for compound XL15 are as follows: MS (ESI, m / z): 765.90 [M+H] + .

[0091] Example 16 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0092] Compound XL03-02 (MW=626, 6.26 g, 0.01 mol) and pyridine (MW=79, 1.58 g, 0.02 mol) were dispersed in dichloromethane (20 g) at room temperature. The mixture was cooled to 0℃~5℃, and 4-trifluoromethylnicotinyl chloride (MW=209, 2.30 g, 0.011 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL03-02 was less than 1%, water (40 g) was added to concentrate the dichloromethane. The mixture was then filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (15 g × 2), 5% sodium hydroxide aqueous solution (15 g × 2), and water (15 g × 2). After drying, the crude product was recrystallized from anhydrous ethanol to obtain compound XL16 (MW=799, 1.86 g), with a yield of 23%. The mass spectrometry data for compound XL16 are as follows: MS (ESI, m / z): 799.90 [M+H] + .

[0093] Example 17 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0094] Compound XL03-02 (MW=626, 6.26 g, 0.01 mol) and pyridine (MW=79, 1.58 g, 0.02 mol) were dispersed in dichloromethane (20 g) at room temperature. The mixture was cooled to 0℃~5℃, and 4-chloro-3-ethyl-1-methylpyrazole-5-acyl chloride hydrochloride (MW=242, 2.66 g, 0.011 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL03-02 was less than 1%, water (40 g) was added to concentrate the dichloromethane. The mixture was then filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (15 g × 2), 5% sodium hydroxide aqueous solution (15 g × 2), and water (15 g × 2). The mixture was dried, and the crude product was recrystallized from anhydrous ethanol to give compound XL17 (MW=796, 1.55 g), with a yield of 19%. The mass spectrometry data for compound XL17 are as follows: MS (ESI, m / z): 796.90 [M+H] + .

[0095] Example 18 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0096] Compound XL03-02 (MW=626, 6.26 g, 0.01 mol) and pyridine (MW=79, 1.58 g, 0.02 mol) were dispersed in dichloromethane (20 g) at room temperature. The mixture was cooled to 0℃~5℃, and 3-difluoromethyl-1-methylpyrazole-4-acyl chloride hydrochloride (MW=230, 2.53 g, 0.011 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL03-02 was less than 1%, water (40 g) was added to concentrate the dichloromethane. The mixture was then filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (15 g × 2), 5% sodium hydroxide aqueous solution (15 g × 2), and water (15 g × 2). The mixture was dried, and the crude product was recrystallized from anhydrous ethanol to give compound XL18 (MW=784, 1.92 g), with a yield of 24%. The mass spectrometry data for compound XL18 are as follows: MS (ESI, m / z): 785.90 [M+H] + .

[0097] Example 19 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0098] Compound XL03-02 (MW=626, 6.26 g, 0.01 mol) and pyridine (MW=79, 1.58 g, 0.02 mol) were dispersed in dichloromethane (20 g) at room temperature. The temperature was lowered to 0℃~5℃, and 2,3,4,5,6-pentafluorobenzoyl chloride (MW=230, 2.53 g, 0.011 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL03-02 was less than 1%, water (40 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (15 g × 2), 5% sodium hydroxide aqueous solution (15 g × 2), and water (15 g × 2). After drying, the crude product was recrystallized from anhydrous ethanol to obtain compound XL19 (MW=820, 4.43 g), with a yield of 54%. The mass spectrometry data for compound XL19 are as follows: MS (ESI, m / z): 820.90 [M+H] + .

[0099] Example 20 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0100] Compound XL03-02 (MW=626, 6.26 g, 0.01 mol) and pyridine (MW=79, 1.58 g, 0.02 mol) were dispersed in dichloromethane (20 g) at room temperature. The mixture was cooled to 0℃~5℃, and 3-nitro-2-fluorobenzoyl chloride (MW=203, 2.23 g, 0.011 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL03-02 was less than 1%, water (40 g) was added to concentrate the dichloromethane. The mixture was then filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (15 g × 2), 5% sodium hydroxide aqueous solution (15 g × 2), and water (15 g × 2). The mixture was dried, and the crude product was recrystallized from anhydrous ethanol to obtain compound XL20 (MW=793, 4.75 g), with a yield of 60%. The mass spectrometry data for compound XL20 are as follows: MS (ESI, m / z): 793.90 [M+H] + .

[0101] Example 21 A method for synthesizing haloalkyl diamide compounds, the specific synthetic route is shown below: .

[0102] Compound XL03-02 (MW=626, 6.26 g, 0.01 mol) and pyridine (MW=79, 1.58 g, 0.02 mol) were dispersed in dichloromethane (20 g) at room temperature. The temperature was lowered to 0℃~5℃, and p-tert-butylbenzoyl chloride (MW=196, 2.16 g, 0.011 mol) was slowly added dropwise. After the addition was complete, the reaction was allowed to proceed at room temperature. The reaction process was monitored by liquid chromatography. When the content of compound XL03-02 was less than 1%, water (40 g) was added to concentrate the dichloromethane. The mixture was filtered, and the filter cake was washed with 5% hydrochloric acid aqueous solution (15 g × 2), 5% sodium hydroxide aqueous solution (15 g × 2), and water (15 g × 2). After drying, the crude product was recrystallized from anhydrous ethanol to obtain compound XL21 (MW=786, 4.93 g), with a yield of 63%. The mass spectrometry data for compound XL21 are as follows: MS (ESI, m / z): 786.90 [M+H] + .

[0103] Test 1: Activity study of beet armyworm.

[0104] The haloalkyl diamide compounds synthesized in Examples 1 to 21 were used as test compounds. 0.05 g of the test compound was dissolved in 1.00 g of DMF to prepare a stock solution with a concentration of 50,000 ppm. The stock solution was diluted with water to three different concentrations: 10 ppm, 50 ppm, and 100 ppm. Leaves of Chinese cabbage were immersed in the stock solutions of different concentrations, dried, and then used to feed 10 4th instar beet armyworm larvae per group. The number of larvae that died was recorded after 24 hours.

[0105] Test 2: Activity study of rice stem borer.

[0106] The haloalkyl diamide compounds synthesized in Examples 1 to 21 were used as test compounds. 0.05 g of the test compound was dissolved in 1.00 g of N,N-dimethylformamide to prepare a stock solution with a concentration of 50,000 ppm. The stock solution was diluted with water to three different concentrations: 10 ppm, 50 ppm, and 100 ppm. Corn stalks were soaked in the stock solutions of different concentrations, dried, and then fed to 4th instar larvae of the rice stem borer (10 larvae per group). After 24 hours, the number of dead larvae was recorded.

[0107] The results of the bioactivity tests of the compounds in Examples 1 to 21 are shown in Table 1.

[0108] Note: "A" represents a mortality rate of 80% to 100%, "B" represents a mortality rate of 50% to 79%, and "C" represents a mortality rate of 0% to 49%.

[0109] As shown in Table 1, the haloalkyl diamide compounds synthesized in Examples 1 to 21 exhibited better killing activity against the beet armyworm than against the rice stem borer. Furthermore, in a low concentration (10 ppm) of the compound mother liquor, some compounds showed better killing activity against both the beet armyworm and the rice stem borer than bromuconazole.

[0110] It should be noted that when numerical ranges are involved in this invention, it should be understood that the two endpoints of each numerical range, as well as any value between the two endpoints, can be selected. Since the steps and methods used are the same as in the embodiments, preferred embodiments are described in this invention to avoid redundancy. Although preferred embodiments of this invention have been described, those skilled in the art, once they understand the basic inventive concept, can make other changes and modifications to these embodiments, and all such changes and modifications fall within the scope of this invention.

[0111] Obviously, those skilled in the art can make various modifications and variations to this invention without departing from its spirit and scope. If these modifications and variations fall within the scope of equivalents of this invention, then this invention also intends to include these modifications and variations.

Claims

1. A haloalkylbisamide compound, characterized in that, The chemical structural formula of the haloalkyl diamide compound is as follows: ； In the formula, X is selected from ketone or sulfonyl groups; R 1 Selected from substituted phenyl, substituted pyridyl, or substituted C5 heteroaryl; R 2 Selected from trifluoromethyl, difluoromethyl, or monofluoromethyl; R 3 Selected from halogens or methyl groups.

2. The haloalkylbisamide compound according to claim 1, characterized in that, R 1 The substituents are selected from at least one of halogen, nitro, cyano, methanesulfonyl, methoxy, C1-C4 alkyl, and C1-C4 haloalkyl.

3. The haloalkylbisamide compound according to claim 1, characterized in that, The heteroatom of the C5 heteroaryl group is selected from at least one of N, O and S.

4. The haloalkylbisamide compound according to claim 1, characterized in that, The haloalkylbisamide compound is selected from one of the following compounds: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。 5. The application of a haloalkyl diamide compound in the preparation of pesticides for controlling pests, characterized in that, The haloalkyl diamide compound is the haloalkyl diamide compound according to any one of claims 1 to 4.

6. The application of the haloalkyl diamide compound according to claim 5 in the preparation of pesticides for controlling pests, characterized in that, When used, the concentration of haloalkyl diamide compounds in pesticides for pest control is 10 ppm to 100 ppm.

7. The application of the haloalkyl diamide compound according to claim 5 in the preparation of pesticides for controlling pests, characterized in that, The pests mentioned are insects containing γ-aminobutyric acid receptors.

8. The application of the haloalkyl diamide compound according to claim 7 in the preparation of pesticides for controlling pests, characterized in that, Insects containing γ-aminobutyric acid receptors include the beet armyworm or the rice stem borer.

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