Γ-aminobutyric acid gated chloride ion channel allosteric modulator compound and use thereof

Abstract

Disclosed in the present invention are a γ-aminobutyric acid gated chloride ion channel allosteric modulator compound and the use thereof, i.e., (S)-4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole-3-yl)-2-methyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)benzamide. The compound has an excellent control effect on pests such as thysanoptera, acarina and lepidoptera, is very friendly to bees, has high environmental ecological safety, can be used for preparing efficient, low-toxicity and safe insecticides, and has wide application prospects in agricultural production.

Description

A compound of allosteric modulator of γ-aminobutyric acid-gated chloride ion channel and its uses Technical Field

[0001] This invention relates to a compound of the class of allosteric modulators of γ-aminobutyric acid-gated chloride ion channels and its uses. It belongs to the technical field of pesticide compounds. Background Technology

[0002] Currently, pesticides remain the most effective method for controlling agricultural pests globally. However, the most common problem in agricultural production is the development of pesticide resistance. To maintain the advantages of modern pesticides in terms of high efficiency, low toxicity, pesticide resistance, environmental friendliness, and economic feasibility, the continuous discovery and development of new products is still necessary.

[0003] Novel insecticides targeting the γ-aminobutyric acid (GABA) receptor-specific site exhibit broad-spectrum activity, high activity, and high selectivity, demonstrating good biological activity against agricultural pests such as Hemiptera, Thysanoptera, Diptera, Lepidoptera, and mites. Currently, Fluxametamide is one of the commercially available insecticides of this class.

[0004] Currently, pesticide application is a crucial means of preventing and controlling plant diseases and pests in agricultural production. However, with the repeated and excessive use of existing pesticides, coupled with improper application by some farmers, some pests are gradually developing significant resistance to common pesticides, making pesticide control increasingly difficult. Developing and researching new pesticides is an effective way to address the problem of pest resistance. Therefore, developing new, highly effective, low-toxicity, and safe insecticides for pest control is of great significance. Summary of the Invention

[0005] The purpose of this invention is to overcome the shortcomings of the prior art. This invention provides a compound of γ-aminobutyric acid-gated chloride ion channel allosteric modulator and its uses.

[0006] To achieve the above objectives, the present invention adopts the following technical solution:

[0007] 1. A compound of the class of allosteric modulators of γ-aminobutyric acid-gated chloride channels or an agriculturally acceptable salt thereof, said compound being (S)-4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazo-3-yl)-2-methyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)benzamide (abbreviated as: S-configuration CCMO-88), with the following chemical structural formula:

[0008] 2. A pharmaceutical composition comprising one of the aforementioned γ-aminobutyric acid-gated chloride channel allosteric modulators or an agriculturally chemically acceptable salt thereof.

[0009] 3. The application of the aforementioned γ-aminobutyric acid-gated chloride channel allosteric modulator compound or its agriculturally acceptable salt in the preparation of agricultural pesticides.

[0010] Preferably, the targets of the agricultural insecticide are: Thysanoptera, Acari, and Lepidoptera.

[0011] More preferably, the target pests of the agricultural insecticide are: thrips, spider mites, and pyralids.

[0012] More preferably, the targets of the agricultural insecticide are: palm thrips, flower thrips, two-spotted spider mite, and rice stem borer.

[0013] 4. Application of the aforementioned pharmaceutical composition in the preparation of agricultural insecticides.

[0014] Preferably, the targets of the agricultural insecticide are: Thysanoptera, Acari, and Lepidoptera.

[0015] More preferably, the target pests of the agricultural insecticide are: thrips, spider mites, and pyralids.

[0016] More preferably, the targets of the agricultural insecticide are: palm thrips, flower thrips, two-spotted spider mite, and rice stem borer.

[0017] 5. An agricultural insecticide, the active ingredient of which is a compound of the aforementioned γ-aminobutyric acid-gated chloride channel allosteric modulator class or an agriculturally chemically acceptable salt thereof.

[0018] 6. An agricultural insecticide comprising the aforementioned pharmaceutical composition.

[0019] The beneficial effects of this invention are:

[0020] This invention discloses an allosteric modulator of γ-aminobutyric acid-gated chloride ion channels, namely (S)-4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazo-3-yl)-2-methyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)benzamide, abbreviated as S-configuration CCMO-88. This compound exhibits excellent control effects against pests such as Thysanoptera, Acari, and Lepidoptera, is very bee-friendly, and has high environmental and ecological safety. It can be used to prepare highly efficient, low-toxicity, and safe insecticides, and has broad application prospects in agricultural production.

[0021] Indoor toxicity tests on palm thrips showed that the S-configuration CCMO-88 was 2.38 times more effective than CCMO-88, more than 326 times more effective than the R-configuration CCMO-88, and 410 times more effective than flurana. Indoor toxicity tests on flower thrips showed that the S-configuration CCMO-88 was approximately twice as effective as CCMO-88, approximately 500 times more effective than the R-configuration CCMO-88, and approximately 200 times more effective than flurana. Indoor toxicity tests on two-spotted spider mites showed that the S-configuration CCMO-88 was 2.03 times more effective than CCMO-88, more than 39 times more effective than the R-configuration CCMO-88, and 9.2 times more effective than flurana. Indoor toxicity tests on rice stem borers showed that the S-configuration CCMO-88 was approximately twice as effective as CCMO-88, approximately 133 times more effective than the R-configuration CCMO-88, and approximately 167 times more effective than flurana. All the above data indicate that the S-configuration CCMO-88 is more effective than CCMO-88 in killing thrips, spider mites, and pyralids, and is significantly more effective than the R-configuration CCMO-88 and flurana.

[0022] Currently, to protect ecosystem health and control the potential adverse environmental impacts of high-risk pesticides at the source, Europe and the United States have proposed comprehensive evaluation systems for the biosafety of pesticides on bees. my country's Ministry of Environmental Protection and Ministry of Agriculture have also included the evaluation of pesticide biotoxicity and safety on bees as an important part of pesticide registration management and environmental safety management for pesticide use. Therefore, the safety evaluation for bees is an essential component of innovative pesticide formulation research. The applicant, referring to GB / T 31270.10-2014 "Chemical Pesticide Environmental Safety Evaluation Test Guidelines Part 10: Acute Toxicity Tests on Bees," conducted oral toxicity tests on bees. The results showed that the acute oral toxicity test result for S-configuration CCMO-88 Italian bees was: LD50. 50 (48 hours) > 11 μg ai / bee, classified as low toxicity according to the acute oral toxicity level of pesticides to bees in the "Guidelines for Environmental Safety Evaluation Tests of Chemical Pesticides"; CCMO-88 Italian honeybee acute oral toxicity test results: LD50 50 (48 hours) 1.8 μg ai / bee, classified as highly toxic according to the acute oral toxicity level of pesticides to bees in the "Guidelines for Environmental Safety Evaluation of Chemical Pesticides"; R configuration CCMO-88 Italian honeybee acute oral toxicity test results: LD50 50 (48 hours) 0.12 μg ai / bee, according to the "Guidelines for Environmental Safety Evaluation Tests of Chemical Pesticides", the acute toxicity level of pesticides to bees is classified as highly toxic; the results of the toxicity test of flurana to Italian bees show that its acute toxicity is highly toxic (LD50). 50The concentration was 0.13 μg ai / bee. The above data show that the S-configuration CCMO-88 is significantly less toxic to bees than CCMO-88, the R-configuration CCMO-88, and fluranarane, making it more bee-friendly, more likely to be developed into a pharmaceutical product, and more feasible for practical agricultural applications, thus having a broader prospect for agricultural application. Attached Figure Description

[0023] Figure 1 shows the proton NMR spectrum of CCMO-88 in the S configuration;

[0024] Figure 2 is the proton spectrum of racemic CCMO-88;

[0025] Figure 3 shows the proton NMR spectrum of CCMO-88 in the R configuration. Detailed Implementation

[0026] The present invention will be further described below with reference to the accompanying drawings and embodiments. It should be noted that the following description is only for explaining the present invention and does not limit its content.

[0027] Example 1: S-configuration CCMO-88

[0028] (S)-4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)benzamide, with the following chemical structural formula:

[0029] The preparation method is as follows:

[0030] (1) Preparation of intermediate one:

[0031] Take 150 g (841.8 mmol) of 4-acetyl-2-methylbenzoic acid (CAS: 55860-35-0, supplier: Dezhou Hanhua Pharmaceutical Chemical Co., Ltd.), 232.8 g (841.8 mmol) of 1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethyl ketone (CAS: 1125812-58-9, supplier: Dezhou Hanhua Pharmaceutical Chemical Co., Ltd.), and 170.3 g (1683 mmol) of triethylamine into a 2000 ml three-necked flask, add 1000 mL of toluene, and start stirring. The mixture was heated under reflux for 24 hours, then the heating was turned off and the mixture was allowed to cool to room temperature. 193 g of 35% concentrated hydrochloric acid was added and the mixture was stirred for 1 hour. The mixture separated into layers, and the toluene layer was concentrated to dryness to give 345 g of (4-(3-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,4-trifluoro-3-hydroxybutyryl)-2-methylbenzoic acid, a white solid, in 90% yield. [MH] - =453.0333

[0032] (2) Preparation of intermediate II:

[0033] In a 2000 mL three-necked flask, 345 g (3-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,4-trifluoro-3-hydroxybutyryl)-2-methylbenzoic acid (758.6 mmol) was added, along with 1380 mL of toluene, 93 g (910 mmol) of acetic anhydride, and DMAP (4-dimethylaminopyridine, 18.5 g, 151.7 mmol). The mixture was heated to reflux and stirred for 12 h. After cooling to room temperature, 79 g (757.62 mmol) of 35% hydrochloric acid was added and the mixture was stirred for 1 h to separate the layers. The toluene layer was concentrated to dryness to give 315 g of a yellow-green solid (4-(3-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,4-trifluorobutyryl)-2-methylbenzoic acid, with a yield of 95%. [MH]-=435.0227

[0034] (3) Preparation of intermediate three:

[0035] Take 315 g (721 mmol) of intermediate bis (4-(3-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,4-trifluorobut-2-enoyl)-2-methylbenzoic acid) and place it in a 2000 mL three-necked flask. Add 1575 mL of toluene and add 128 g (1082 mmol) of thionyl chloride while stirring. Heat to reflux for 2 hours and concentrate the reaction solution to dryness to obtain concentrated acyl chloride solution for later use.

[0036] Take 166.6 g (866 mmol) of (2-amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride) (CAS: 1171331-39-7, supplier: Dezhou Hanhua Pharmaceutical Chemical Co., Ltd.), 109.5 g (1082 mmol) of triethylamine, and 945 ml of toluene into a 2000 ml three-necked flask and stir for 1 hour. Add the concentrated acyl chloride solution from the previous step and continue stirring for 12 hours. A large amount of solid precipitates, indicating that the TLC acyl chloride reaction is complete. Add 1 L of purified water and stir for 1 hour. Filter, and place the filter cake in a 50°C forced-air oven to dry for 12 hours to obtain 331.7 g of a yellow-green solid (4-(3-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,4-trifluorobut-2-enoyl)-2-methyl-N-(2-oxo-2-((2,2-trifluoroethyl)amino)ethyl)benzamide, yield 80%. [M+H] + =575.0774, [MH] - =573.0634

[0037] (4) Preparation of S-configuration CCMO-88:

[0038] Add (57.5 g, 100 mmol) of (4-(3-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,4-trifluorobut-2-enoyl)-2-methyl-N-(2-oxo-2-((2,2-trifluoroethyl)amino)ethyl)benzamide and (5.96 g, 10 mmol) of N-(acridin-9-ylmethyl)quinine bromide (CAS: 466639-23-6, supplier: Dezhou Hanhua Pharmaceutical Chemical Co., Ltd.) to 500 mL of dichloromethane, and add 200 mL of 10% sodium hydroxide aqueous solution while stirring. Then add hydrochloric acid in portions. Hydroxylamine (20.85 g, 300 mmol) was stirred for 12 hours, allowed to stand in layers, and the dichloromethane layer was washed with 100 ml of 2 M hydrochloric acid. The mixture was then concentrated under reduced pressure, and a solid gradually precipitated out. 200 mL of water was added and the mixture was further concentrated to remove the dichloromethane. The mixture was stirred for 1 hour, filtered, and the filter cake was washed with water and dried to obtain 50 g of (S)-4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)benzamide, with a yield of 85%.

[0039] The hydrogen spectrum of the product is shown in Figure 1.

[0040] 1 H NMR(400MHz, CDCl3)δ7.82(s,1H),7.76(s,1H),7.69(s,1H),7.45–7.54(m,2H),7.46(d,1H) ,7.11(t,1H),6.82(t,1H),4.21(d,2H),4.16(d,1H),3.94(m,2H),3.75(d,1H),2.46(s,3H)C 23 H 17 ClF9N3O3, [M+H] + =590.0884, [MH] - =588.0743

[0041] Comparative Example 1: CCMO-88

[0042] The racemic form, 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)benzamide, has the following chemical structural formula:

[0043] The preparation method is as follows:

[0044] (1) Preparation of intermediate three, same as in Example 1.

[0045] (2) Preparation of racemic CCMO-88:

[0046] Add 57.5 g (100 mmol) of (4-(3-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,4-trifluorobut-2-enoyl)-2-methyl-N-(2-oxo-2-((2,2-trifluoroethyl)amino)ethyl)benzamide to 500 mL of dichloromethane, and while stirring, add 200 mL of 10% sodium hydroxide aqueous solution. Then add 20.85 g (300 mmol) of hydroxylamine hydrochloride in portions, and continue stirring for 12 hours. Allow the mixture to separate into layers and stand. The dichloromethane layer was washed with 100 ml of 2M hydrochloric acid, then concentrated under reduced pressure until a solid gradually precipitated. 200 mL of water was added and the concentration continued until the dichloromethane was removed and dried. The mixture was stirred for 1 hour, filtered, and the filter cake was washed with water and dried to obtain 52 g of 4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)benzamide, with a yield of 88.4%.

[0047] The hydrogen spectrum of the product is shown in Figure 2.

[0048] 1 H NMR (600MHz, CDCl3) δ7.82(s,1H),7.76(s,1H),7.69(s,1H),7.55(s,1H),7.52(d,1H),7.47(d,1 H),6.93(t,1H),6.72(t,1H),4.21(d,2H),4.16(d,1H),3.95(qd,2H),3.74(d,1H),2.47(s,3H).C 23 H 17 ClF9N3O3, [M+H] + =590.0884, [MH] - =588.0743

[0049] Comparative Example 2: CCMO-88 in R configuration

[0050] The chemical structure of compound (R)-4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazo-3-yl)-2-methyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)benzamide is as follows:

[0051] The preparation method is as follows:

[0052] (1) Preparation of intermediate three, same as in Example 1.

[0053] (2) Preparation of R-configuration CCMO-88:

[0054] Add (4-(3-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,4-trifluorobut-2-enoyl)-2-methyl-N-(2-oxo-2-((2,2-trifluoroethyl)amino)ethyl)benzamide (57.5 g, 100 mmol) and (1S,2R,4S,5R)-1-(acridin-9-ylmethyl)-2-((S)-hydroxy(6-methoxyquinoline-4-yl)methyl)-5-vinylquinine-1-ammonium bromide (supplier: Dezhou Hanhua Pharmaceutical Chemical Co., Ltd.) (5.96 g, 10 mmol) to 500 mL of dichloromethane, and then add 10% hydroxide solution while stirring. 200 ml of sodium aqueous solution was mixed with hydroxylamine hydrochloride (20.85 g, 300 mmol) in portions, and the mixture was stirred for 12 hours. The mixture was allowed to stand in layers, and the dichloromethane layer was washed with 100 ml of 2 M hydrochloric acid. The mixture was then concentrated under reduced pressure, and a solid gradually precipitated out. 200 mL of water was added, and the mixture was further concentrated to remove the dichloromethane. The mixture was stirred for 1 hour, filtered, and the filter cake was washed with water and dried to obtain 48 g of (R)-4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)benzamide, with a yield of 81.6%.

[0055] The hydrogen spectrum of the product is shown in Figure 3.

[0056] 1 H NMR (400MHz, DMSO) δ8.62(s,2H),8.09(s,1H),7.98(s,1H),7.87(s,1H),7.63(s,2H),7.52(d,1H),4.43(q,2H),3.96(m,4H),2.41(s,3H).C 23 H 17 ClF9N3O3, [M+H] + =590.0884, [MH] - =588.0727

[0057] Comparative Example 3: Fluoranar (CAS: 864731-61-3, Supplier: Dezhou Hanhua Pharmaceutical Chemical Co., Ltd.)

[0058] The chemical structural formula is as follows:

[0059] Test case

[0060] 1. Toxicological studies

[0061] According to Part 10, "Acute Toxicity Tests for Bees," of the "Guidelines for Environmental Safety Evaluation of Chemical Pesticides" (GB / T 31270.10-2014), the acute toxicity of pesticides to bees is determined by LD50. 50 The size of (48h) is divided into four levels:

[0062] LD 50 >11.0 μg ai / bee is considered low toxicity.

[0063] 2.00μg ai / bee <LD 50 ≤11.0 μg ai / bee indicates poisoning.

[0064] 0.001μg ai / bee <LD 50 ≤2.00μg ai / bee is highly toxic.

[0065] LD 50 ≤0.001μg ai / bee is highly toxic.

[0066] The toxicity test results for each compound are shown in Table 1.

[0067] Table 1. Toxicity Test Results

[0068] As shown in Table 1, the compound in Example 1 is significantly less toxic to beneficial insects like bees than the compounds in Comparative Examples 1-3. It is more bee-friendly, has greater potential for pharmaceutical development, and is feasible for practical agricultural applications, thus showing broader prospects for agricultural use.

[0069] 2. Effectiveness of agricultural pest control

[0070] The compounds from Example 1 and Comparative Examples 1-3 were used to control various agricultural pests.

[0071] This experiment, conducted in accordance with the People's Republic of China agricultural industry standard "Guidelines for Indoor Bioassay Tests of Pesticides - Insecticides Part 8: Filter Paper Film Method" (NY / T 1154.8-2007), determined the indoor toxicity of four technical grade pesticides to palm thrips and flower thrips.

[0072] This experiment was conducted in accordance with the People's Republic of China Agricultural Industry Standard "Guidelines for Indoor Bioassay of Pesticides - Insecticides Part 12: Tetranychus Slide Immersion Method" (NY / T 1154.12-2008) to determine the indoor toxicity of four technical pesticides to the two-spotted spider mite.

[0073] This experiment, conducted in accordance with the People's Republic of China Agricultural Industry Standard "Guidelines for Indoor Bioassay Tests of Pesticides - Insecticides Part 16: Activity Tests Against Whiteflies - Agar Moisture Dipping Method" (NY / T 1154.16-2013), determined the indoor toxicity of four technical pesticides against whiteflies.

[0074] This experiment, conducted in accordance with the People's Republic of China Agricultural Industry Standard "Guidelines for Indoor Bioassay of Pesticides - Insecticides Part 6: Activity Test - Immersion Method" (NY / T 1154.6-2006), determined the indoor toxicity of four technical grade pesticides to the rice stem borer.

[0075] The data on the indoor toxicity of compounds in Example 1 and Comparative Examples 1-3 to palm thrips are shown in Tables 2-1 to 2-4.

[0076] Table 2-1. Indoor toxicity test data of the compound in Example 1 against palm thrips

[0077] Table 2-2. Indoor toxicity test data of compound 1 against palm thrips.

[0078] Table 2-3. Indoor toxicity test data of compound 2 against palm thrips.

[0079] Table 2-4. Indoor toxicity test data of compound 3 against palm thrips.

[0080] The insecticidal rate data of compounds in Example 1 and Comparative Examples 1-3 against thrips are shown in Table 3.

[0081] Table 3. Insecticidal rate data of compounds against thrips

[0082] The data on the indoor toxicity of compounds in Example 1 and Comparative Examples 1-3 to Tetranychus bicolor are shown in Tables 4-1 to 4-4.

[0083] Table 4-1. Indoor toxicity test data of the compound in Example 1 against Tetranychus bisaurae.

[0084] Table 4-2. Indoor toxicity test data of compound 1 against Tetranychus bistigma.

[0085] Table 4-3. Indoor toxicity test data of compound 2 against Tetranychus bisaurae.

[0086] Table 4-4. Indoor toxicity test data of compound 3 against Tetranychus bisaurae.

[0087] The data on the indoor toxicity of compounds in Example 1 and Comparative Examples 1-3 against whiteflies are shown in Tables 5-1 to 5-4.

[0088] Table 5-1. Indoor toxicity test data of the compound in Example 1 against whiteflies.

[0089] Table 5-2. Indoor toxicity test data of compound 1 against whiteflies in Comparative Example 1

[0090] Table 5-3. Indoor toxicity test data of compound 2 against whiteflies.

[0091] Table 5-4. Indoor toxicity test data of compound 3 against whiteflies in Comparative Example 3.

[0092] The insecticidal rate data of compounds in Example 1 and Comparative Examples 1-3 against rice stem borer are shown in Table 6.

[0093] Table 6. Insecticidal data of compounds against rice stem borer

[0094] Table 7 shows a comparison of the control effects of various compounds on agricultural pests.

[0095] Calculation method:

[0096] Using the logarithm of drug concentration (mg / L) as the independent variable X and the probability of corrected mortality as the dependent variable Y, the LC-value of the toxicity regression line was calculated using DPS software. 50 value.

[0097] Table 7. Comparison of the control effects of compounds on agricultural pests

[0098] As shown in Table 8, compared with Comparative Examples 1-3, the compound of Example 1 has significantly better control effects against palm thrips, flower thrips, two-spotted spider mites, and rice stem borers. For whiteflies, the control effect of the compound of Example 1 is comparable to that of Comparative Examples 1 and 2, and slightly better than that of Comparative Example 3. Palm thrips and flower thrips are typical representatives of Thysanoptera pests, two-spotted spider mites are typical representatives of Acari pests, and rice stem borers are typical representatives of Lepidoptera pests. Therefore, it can be concluded that the compound of Example 1 has significantly better control effects against Thysanoptera, Acari, and Lepidoptera pests.

[0099] Although the specific embodiments of the present invention have been described above in conjunction with the accompanying drawings, this is not intended to limit the scope of protection of the present invention. Based on the technical solutions of the present invention, various modifications or variations that can be made by those skilled in the art without creative effort are still within the scope of protection of the present invention.

Claims

1. A compound of the class of allosteric modulators of γ-aminobutyric acid-gated chloride channels or an agriculturally chemically acceptable salt thereof, characterized in that, The compound is (S)-4-(5-(3-chloro-5-(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)benzamide, with the following chemical structural formula:

2. A pharmaceutical composition, characterized in that, It includes a compound of the class of allosteric modulators of γ-aminobutyric acid-gated chloride channels as described in claim 1, or an agriculturally chemically acceptable salt thereof.

3. The use of the γ-aminobutyric acid-gated chloride channel allosteric modulator compound of claim 1 or its agriculturally chemically acceptable salt in the preparation of agricultural pesticides.

4. The application according to claim 3, characterized in that, The target pests controlled by the agricultural pesticides are: Thysanoptera, Acari, and Lepidoptera.

5. The use of the pharmaceutical composition of claim 2 in the preparation of agricultural insecticides.

6. The application according to claim 5, characterized in that, The target pests controlled by the agricultural pesticides are: Thysanoptera, Acari, and Lepidoptera.

7. An agricultural insecticide, characterized in that, Its active ingredient is a compound of the γ-aminobutyric acid-gated chloride channel allosteric modulator class as described in claim 1, or an agriculturally chemically acceptable salt thereof.

8. An agricultural insecticide, characterized in that, It comprises the pharmaceutical composition of claim 2.

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