Gamma-aminobutyric acid gated chloride ion channel allosteric regulator compound and application thereof

Abstract

The invention discloses a gamma-aminobutyric acid gated chloride ion channel allosteric modifier compound and an application thereof, namely (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, and a preparation method of the gamma-aminobutyric acid gated chloride ion channel allosteric modifier compound. The compound has an excellent control effect on pests of thysanoptera, acarina, lepidoptera and the like, is very friendly to bees and high in environmental ecological safety, can be used for preparing efficient, low-toxicity and safe insecticides, and has a wide application prospect in agricultural production.

Description

Technical Field

[0001] The present invention relates to a γ-aminobutyric acid-gated chloride ion channel allosteric modulator compound and its application, belonging to the technical field of pesticide compounds. Background Art

[0002] Currently, the use of pesticides is still the most effective way to control agricultural pests worldwide. In the actual process of agricultural production, the most common problem in pest control is the development of pesticide resistance. In order to maintain the advantages of modern pesticides in terms of high efficiency, low toxicity, pesticide resistance, environmental friendliness and economic feasibility, it is still necessary to continuously discover and develop new products.

[0003] A new type of insecticide specific to γ-aminobutyric acid (GABA) receptors, with broad spectrum, high activity, high selectivity, etc., has good biological activity against agricultural pests such as Hemiptera, Thysanoptera, Diptera, Lepidoptera, and mites. Currently, the products of this type of compound listed as pesticides include Fluxametamide.

[0004] At present, in agricultural production, the application of pesticides is an important means of preventing and controlling plant diseases and insect pests. However, with the repeated and large-scale use of existing pesticides and the improper application of pesticides by some farmers, some pests have gradually begun to develop a relatively large resistance to existing common pesticides, and the difficulty of pesticide control has become increasingly greater. For this problem, the development and research of new drugs is an effective way to deal with the problem of pest resistance. Therefore, it is of great significance to develop new high-efficiency, low-toxic and safe pesticides for pest control. Summary of the invention

[0005] The purpose of the present invention is to overcome the deficiencies of the prior art. The present invention provides a γ-aminobutyric acid-gated chloride channel allosteric modulator compound and its use.

[0006] To achieve the above object, the present invention adopts the following technical solutions:

[0007] 1. A γ-aminobutyric acid-gated chloride channel allosteric modulator compound or an agriculturally chemically acceptable salt thereof, wherein 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 (abbreviated as: S-configuration CCMO-88), and the chemical structure is as follows:

[0008]

[0009] 2. A pharmaceutical composition comprising the aforementioned γ-aminobutyric acid-gated chloride channel allosteric modulator compound or an agrochemically acceptable salt thereof.

[0010] 3. Use of the aforementioned γ-aminobutyric acid-gated chloride channel allosteric modulator compound or its agrochemically acceptable salt in the preparation of agricultural pesticides.

[0011] Preferably, the agricultural pesticide targets the following orders: Thysanoptera, Acarina, and Lepidoptera.

[0012] Further preferably, the control targets of the agricultural pesticide are: Thripidae, Tetranychus, and Pyralidae.

[0013] More preferably, the agricultural pesticide is used to control palm thrips, flower thrips, two-spotted spider mite, and striped stem borer.

[0014] 4. Use of the aforementioned pharmaceutical composition in the preparation of agricultural pesticides.

[0015] Preferably, the agricultural pesticide targets the following orders: Thysanoptera, Acarina, and Lepidoptera.

[0016] Further preferably, the control targets of the agricultural pesticide are: Thripidae, Tetranychus, and Pyralidae.

[0017] More preferably, the agricultural pesticide is used to control palm thrips, flower thrips, two-spotted spider mite, and striped stem borer.

[0018] 5. An agricultural insecticide, the active ingredient of which is the aforementioned γ-aminobutyric acid-gated chloride channel allosteric modulator compound or an agrochemically acceptable salt thereof.

[0019] 6. An agricultural pesticide comprising the aforementioned pharmaceutical composition.

[0020] Beneficial effects of the present invention:

[0021] The invention discloses a γ-aminobutyric acid-gated chloride channel allosteric modulator compound, namely (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, referred to as S-configuration CCMO-88. The compound has excellent control effects on pests such as Thysanoptera, Acarina, and Lepidoptera, is very friendly to bees, has high environmental ecological safety, can be used for the preparation of high-efficiency, low-toxicity, and safe insecticides, and has broad application prospects in agricultural production.

[0022] The results of the indoor toxicity test of palm thrips showed that the efficacy of S-configuration CCMO-88 was 2.38 times that of CCMO-88, more than 326 times that of R-configuration CCMO-88, and 410 times that of flurelana. The results of the indoor toxicity test of flower thrips showed that the efficacy of S-configuration CCMO-88 was about 2 times that of CCMO-88, about 500 times that of R-configuration CCMO-88, and about 200 times that of flurelana. The results of the indoor toxicity test of two-spotted spider mite showed that the efficacy of S-configuration CCMO-88 was 2.03 times that of CCMO-88, more than 39 times that of R-configuration CCMO-88, and 9.2 times that of flurelana. The results of the indoor toxicity test of striped stem borer showed that the efficacy of S-configuration CCMO-88 was about 2 times that of CCMO-88, about 133 times that of R-configuration CCMO-88, and about 167 times that of flurelana. The above data all show that the killing effect of S-configuration CCMO-88 on pests of Thripidae, Tetranychus and Pyralidae is better than that of CCMO-88, and is significantly better than that of R-configuration CCMO-88 and Flurelana.

[0023] At present, in order to protect the health of the ecosystem and control the potential adverse effects of high-risk pesticides on the environment and ecology from the source, Europe and the United States have proposed a complete pesticide biosafety evaluation system for bees. my country's Ministry of Environmental Protection and Ministry of Agriculture have also listed the biological toxicity and safety evaluation of pesticides on bees as an important part of pesticide registration management and pesticide use environmental safety management. Therefore, the safety evaluation of bees is an indispensable part of the research on the drugability of innovative pesticides. The applicant conducted oral toxicity testing on bees with reference to GB / T31270.10-2014 "Chemical Pesticide Environmental Safety Evaluation Test Guidelines Part 10: Acute Toxicity Test for Bees". The results showed that the acute oral toxicity test results of S-configuration CCMO-88 Italian bees: LD 50 (48 hours)>11μg ai / bee, which is low toxicity according to the classification standard of acute toxicity of pesticides to bees in the "Chemical Pesticide Environmental Safety Evaluation Test Guidelines"; CCMO-88 Italian honey bee acute oral toxicity test results: LD 50 (48 hours) 1.8μg ai / bee, according to the classification standard of acute toxicity of pesticides to bees in the "Chemical Pesticide Environmental Safety Evaluation Test Guidelines", it is highly toxic; the results of the acute oral toxicity test of R-configuration CCMO-88 Italian honey bees: LD 50 (48 hours) 0.12μg ai / bee, according to the classification standard of acute toxicity of pesticides to bees in the "Chemical Pesticide Environmental Safety Evaluation Test Guidelines", it is highly toxic; the results of the toxicity test of flurellana on Italian honey bees showed that the acute toxicity was highly toxic (LD 50The above data show that the toxicity of CCMO-88 with S configuration to bees is significantly lower than that of CCMO-88, CCMO-88 with R configuration and flurellana, which is more friendly to bees, has a higher possibility of drug development and practical application in agriculture, and has a broader prospect for agricultural application. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 This is the hydrogen spectrum of CCMO-88 in S configuration;

[0025] Figure 2 This is the hydrogen spectrum of racemic CCMO-88;

[0026] Figure 3 This is the hydrogen spectrum of CCMO-88 in R configuration. DETAILED DESCRIPTION

[0027] The present invention is further described below in conjunction with 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 contents.

[0028] Example 1: CCMO-88 in S configuration

[0029] (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, the chemical structure is as follows:

[0030]

[0031] The preparation method is as follows:

[0032]

[0033] (1) Preparation of intermediate 1:

[0034] Take 4-acetyl-2-methylbenzoic acid (CAS: 55860-35-0, supplier: Dezhou Hanhua Pharmaceutical Chemical Co., Ltd.) (150 g, 841.8 mmol), 1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone (CAS: 1125812-58-9, supplier: Dezhou Hanhua Pharmaceutical Chemical Co., Ltd.) (232.8 g, 841.8 mmol), and triethylamine (170.3 g, 1683 mmol) into a 2000 ml three-necked flask, add 1000 mL of toluene, and start stirring. The mixture was heated to reflux for 24 hours, the heating was turned off, the temperature was cooled to room temperature, 193 g of 35% concentrated hydrochloric acid was added, and the mixture was stirred for 1 hour. The layers were separated, and the toluene layer was concentrated to dryness to obtain (4-(3-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,4-trifluoro-3-hydroxybutyryl)-2-methylbenzoic acid), 345 g of white solid, with a yield of 90%. [MH] - =453.0333

[0035] (2) Preparation of Intermediate 2:

[0036] In a 2000mL three-necked flask, add (4-(3-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,4-trifluoro-3-hydroxybutyryl)-2-methylbenzoic acid) (345g, 758.6mmol), add 1380mL of toluene, add acetic anhydride (93g, 910mmol), DMAP (4-dimethylaminopyridine, 18.5g, 151.7mmol), heat to reflux and stir for 12h. Cool to room temperature, add 35% hydrochloric acid (79g, 757.62mmol) and stir for 1 hour to separate the layers. Concentrate the toluene layer to dryness to obtain 315g of yellow-green solid (4-(3-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,4-trifluorobut-2-enoyl)-2-methylbenzoic acid), with a yield of 95%. [MH]-=435.0227

[0037] (3) Preparation of intermediate 3:

[0038] Take (4-(3-(3-chloro-5-(trifluoromethyl)phenyl)-4,4,4-trifluorobut-2-enoyl)-2-methylbenzoic acid) intermediate II (315 g, 721 mmol) and put it into a 2000 mL three-necked flask, add 1575 mL of toluene, add thionyl chloride (128 g, 1082 mmol) under stirring, heat and reflux for 2 hours, concentrate the reaction solution to dryness, and obtain the concentrated acid chloride solution for standby use.

[0039] Take (2-amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride) (CAS: 1171331-39-7, supplier: Dezhou Hanhua Pharmaceutical Chemical Co., Ltd.) (166.6g, 866mmol), triethylamine (109.5g, 1082mmol) and 945ml of toluene into a 2000ml 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. After the acyl chloride reaction is completed by TLC, add 1L of purified water and stir for 1 hour. Filter and put the filter cake into a 50°C blast oven and dry for 12 hours to obtain 331.7g of 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) with a yield of 80%. [M+H] + =575.0774, [MH] - =573.0634

[0040] (4) Preparation of CCMO-88 with S configuration:

[0041] (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), N-(acridin-9-ylmethyl)quinine bromide (CAS: 466639-23-6, supplier: Dezhou Hanhua Pharmaceutical Chemical Co., Ltd.) (5.96 g, 10 mmol) were added to 500 mL of dichloromethane, 200 ml of 10% sodium hydroxide aqueous solution was added under stirring, and hydrochloric acid was added in portions. Hydroxylamine (20.85 g, 300 mmol) was added, and stirring was continued for 12 hours. The mixture was separated and allowed to stand for stratification. The dichloromethane layer was washed with 100 ml of 2M hydrochloric acid, and then concentrated under reduced pressure to gradually precipitate solids. 200 mL of water was added and the dichloromethane was dried. 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%.

[0042] The product hydrogen spectrum is shown in Figure 1 .

[0043] 1H 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 CIF 9 N 3 O 3 , [M+H] + =590.0884, [MH] - =588.0743

[0044] Comparative Example 1: CCMO-88

[0045] The racemic 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 structure:

[0046]

[0047] The preparation method is as follows:

[0048]

[0049] (1) Preparation of Intermediate 3 is the same as in Example 1.

[0050] (2) Preparation of racemic CCMO-88:

[0051] 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) into 500 mL of dichloromethane, add 200 ml of 10% sodium hydroxide aqueous solution under stirring, add hydroxylamine hydrochloride (20.85 g, 300 mmol) in portions, continue stirring for 12 hours, separate the layers and stand for 3 hours. The mixture was allowed to stand for 2 hours, and the dichloromethane layer was washed with 100 ml of 2M hydrochloric acid. The mixture was then concentrated under reduced pressure to gradually precipitate a solid. 200 ml of water was added and the mixture was further concentrated to dry the dichloromethane. The mixture was stirred for 1 hour, filtered, and the filter cake was washed with water and dried to give 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 in a yield of 88.4%.

[0052] The product hydrogen spectrum is shown in Figure 2 .

[0053] 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 CIF 9 N 3 O 3 , [M+H] + =590.0884, [MH] - =588.0743

[0054] Comparative Example 2: CCMO-88 with R configuration

[0055] The compound (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 has the following chemical structure:

[0056]

[0057] The preparation method is as follows:

[0058]

[0059] (1) Preparation of Intermediate 3 is the same as in Example 1.

[0060] (2) Preparation of CCMO-88 with R configuration:

[0061] (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), (1S, 2R, 4S, 5R)-1-(acridin-9-ylmethyl)-2-((S)-hydroxy(6-methoxyquinolin-4-yl)methyl)-5-vinylquinin-1-ammonium bromide (supplier: Dezhou Hanhua Pharmaceutical Chemical Co., Ltd.) (5.96 g, 10 mmol) were added to 500 mL of dichloromethane, and 10% mass concentration of hydroxide was added under stirring. To 200 ml of sodium aqueous solution, hydroxylamine hydrochloride (20.85 g, 300 mmol) was added in portions, and stirring was continued for 12 hours. The mixture was separated and allowed to stand for stratification. The dichloromethane layer was washed with 100 ml of 2M hydrochloric acid, and then concentrated under reduced pressure to gradually precipitate solids. 200 mL of water was added and the dichloromethane was dried. 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%.

[0062] The product hydrogen spectrum is shown in Figure 3 .

[0063] 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 CIF 9 N 3 O 3 , [M+H] + =590.0884, [MH] - =588.0727

[0064] Comparative Example 3: Flurellana (CAS: 864731-61-3, supplier: Dezhou Hanhua Pharmaceutical Chemical Co., Ltd.)

[0065] The chemical structure is as follows:

[0066]

[0067] Test example

[0068] 1. Toxicology studies

[0069] According to Part 10 "Acute Toxicity Test for Bees" of the "Test Guidelines for Environmental Safety Assessment of Chemical Pesticides" (GB / T 31270.10-2014), the acute toxicity of pesticides to bees is measured according to the LD 50 The size of (48h) is divided into four levels:

[0070] LD 50 >11.0μg ai / bee is low toxicity,

[0071] 2.00μg ai / bee <LD 50 ≤11.0μg ai / bee is considered poisoning.

[0072] 0.001μg ai / bee <LD 50 ≤2.00μg ai / bee is highly toxic,

[0073] LD 50 ≤0.001μg ai / bee is highly toxic.

[0074] The toxicity test results of each compound are shown in Table 1.

[0075] Table 1. Toxicity test results

[0076]

[0077] As shown in Table 1, the toxicity of the compound in Example 1 to the beneficial insect bees is significantly lower than that of the compounds in Comparative Examples 1 to 3, and the compound is more friendly to bees, has a greater possibility of being made into medicine and has practical feasibility for agricultural application, and has a broader prospect for agricultural application.

[0078] 2. Agricultural pest control effect

[0079] The compounds of Example 1 and Comparative Examples 1 to 3 were respectively used for controlling various agricultural pests.

[0080] This test was conducted in accordance with the agricultural industry standard of the People's Republic of China "Guidelines for Indoor Bioassay Tests of Pesticides - Insecticides Part 8: Filter Paper Film Method" (NY / T 1154.8-2007) to determine the indoor toxicity of four original pesticides to palm thrips and flower thrips.

[0081] This test was conducted in accordance with the agricultural industry standard of the People's Republic of China "Guidelines for Indoor Bioassay Tests of Pesticides - Insecticides Part 12: Slide Dip Method for Spider Mites" (NY / T 1154.12-2008) to determine the indoor toxicity of four original pesticides to two-spotted spider mites.

[0082] This test was conducted in accordance with the agricultural industry standard of the People's Republic of China "Guidelines for Indoor Bioassay Tests of Pesticides - Insecticides Part 16: Agar Moisture Leaf Dip Method for Activity Tests against Whiteflies" (NY / T 1154.16-2013), to determine the indoor toxicity of four technical pesticides to Bemisia tabaci.

[0083] This test was conducted in accordance with the agricultural industry standard of the People's Republic of China "Guidelines for Indoor Bioassay Tests of Pesticides - Insecticides Part 6: Activity Test - Insect Immersion Method" (NY / T 1154.6-2006) to determine the indoor toxicity of four original pesticides to Chilo suppressalis.

[0084] The indoor toxicity test data of the compounds of Example 1 and Comparative Examples 1 to 3 against Thrips palmi are shown in Tables 2-1 to 2-4.

[0085] Table 2-1. Indoor toxicity test data of the compound of Example 1 against Thrips palmi

[0086]

[0087]

[0088] Table 2-2. Comparative Example 1 compound indoor toxicity test data on Thrips palmi

[0089]

[0090]

[0091] Table 2-3. Comparative Example 2 compound indoor toxicity test data on Thrips palmi

[0092]

[0093]

[0094] Table 2-4. Comparative Example 3 compound indoor toxicity test data on Thrips palmi

[0095]

[0096]

[0097] The insecticidal rates of the compounds of Example 1 and Comparative Examples 1 to 3 against flower thrips are shown in Table 3.

[0098] Table 3. Data on the insecticidal rate of compounds against flower thrips

[0099]

[0100]

[0101] The indoor toxicity test data of the compounds of Example 1 and Comparative Examples 1 to 3 against Tetranychus urticae are shown in Tables 4-1 to 4-4.

[0102] Table 4-1. Indoor toxicity test data of the compound of Example 1 against Tetranychus urticae

[0103]

[0104]

[0105] Table 4-2. Comparative Example 1 compound indoor toxicity test data on two-spotted spider mite

[0106]

[0107] Table 4-3. Comparative Example 2 compound indoor toxicity test data on two-spotted spider mite

[0108]

[0109]

[0110] Table 4-4. Comparative Example 3 compound indoor toxicity test data on two-spotted spider mite

[0111]

[0112]

[0113] The indoor toxicity test data of the compounds of Example 1 and Comparative Examples 1 to 3 to Bemisia tabaci are shown in Tables 5-1 to 5-4.

[0114] Table 5-1. Indoor toxicity test data of the compound of Example 1 against Bemisia tabaci

[0115]

[0116]

[0117] Table 5-2. Comparative Example 1 compound indoor toxicity test data on Bemisia tabaci

[0118]

[0119] Table 5-3. Comparative Example 2 compound indoor toxicity test data on Bemisia tabaci

[0120]

[0121]

[0122] Table 5-4. Comparative Example 3 compound indoor toxicity test data on Bemisia tabaci

[0123]

[0124]

[0125] The insecticidal rates of the compounds of Example 1 and Comparative Examples 1 to 3 against Chilo suppressalis are shown in Table 6.

[0126] Table 6. Data on the insecticidal rate of compounds against Chilo suppressalis

[0127]

[0128]

[0129] The comparison of the control effects of various compounds on agricultural pests is shown in Table 7.

[0130] Calculation method:

[0131]

[0132] Using the logarithm of the drug concentration (mg / L) as the independent variable X and the probability value of the corrected mortality rate as the dependent variable Y, the LC of the toxicity regression line was calculated using the DPS software. 50 value.

[0133] Table 7. Comparison of the control effects of compounds on agricultural pests

[0134]

[0135] As shown in Table 8, compared with Comparative Examples 1 to 3, the compound of Example 1 has significantly better control effects on palm thrips, flower thrips, two-spotted spider mites, and striped stem borer; for Bemisia tabaci, the control effects of the compound of Example 1 are equivalent to those of the compounds of Comparative Examples 1 and 2, and slightly better than the compound of Comparative Example 3. Palm thrips and flower thrips are typical representatives of Thysanoptera pests, two-spotted spider mites are typical representatives of Acarina pests, and striped stem borer is a typical representative of Lepidoptera pests, so it can be concluded that the compound of Example 1 has significantly better control effects on Thysanoptera, Acarina, and Lepidoptera pests.

[0136] Although the above describes the specific implementation mode of the present invention in conjunction with the accompanying drawings, it is not intended to limit the scope of protection of the present invention. Based on the technical solution of the present invention, various modifications or variations that can be made by those skilled in the art without creative work are still within the scope of protection of the present invention.

Claims

1. A γ-aminobutyric acid-gated chloride channel allosteric modulator compound 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, and the chemical structure is as follows:

2. A pharmaceutical composition, characterized in that The invention comprises a γ-aminobutyric acid-gated chloride channel allosteric modulator compound as described in claim 1 or an agrochemically acceptable salt thereof.

3. Use of a γ-aminobutyric acid-gated chloride channel allosteric modulator compound or an agrochemically acceptable salt thereof as claimed in claim 1 in the preparation of agricultural pesticides.

4. The use according to claim 3, characterized in that: The control objects of the agricultural insecticide are: Thysanoptera, Acarina, and Lepidoptera.

5. Use of the pharmaceutical composition according to claim 2 in the preparation of agricultural pesticides.

6. The use according to claim 5, characterized in that: The control objects of the agricultural insecticide are: Thysanoptera, Acarina, and Lepidoptera.

7. An agricultural pesticide, characterized in that: The active ingredient is a γ-aminobutyric acid-gated chloride channel allosteric regulator compound or an agrochemically acceptable salt thereof as described in claim 1.

8. An agricultural pesticide, characterized in that Comprising the pharmaceutical composition according to claim 2.

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