A phenyl isoxazole derivative containing a triazole ring and a preparation method and application thereof

Abstract

The application relates to the technical field of pesticide chemistry, and discloses a phenyl isoxazole derivative containing a triazole ring as well as a preparation method and application thereof. The phenyl isoxazole derivative containing the triazole ring has the structural formula: The phenyl isoxazole derivative containing the triazole ring provided by the application has good insecticidal activity on agricultural pests such as Plutella xylostella, Spodoptera frugiperda, Helicoverpa armigera, Ostrinia nubilalis, and aphids when the concentration is 50 mu g / mL. Therefore, the phenyl isoxazole derivative containing the triazole ring provided by the application can be applied to the prevention and control of agricultural pests as an active pesticide ingredient.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of pesticide chemistry, in particular to a phenyl isoxazole derivative containing a triazole ring and a preparation method and application thereof. BACKGROUND

[0002] With the development of green pesticides, isoxazole compounds are widely used in various insecticides, for example, isoxazole compounds are contained in fluralaner, isoxazoles, isoxazoles, isoxazoles, and isoxazoles. The isoxazole insecticide is favored by agricultural workers due to its high activity, low toxicity, long persistence and other advantages, and has high insecticidal activity on Lepidoptera, Hemiptera, Thysanoptera, Coleoptera, Diptera and Acarina.

[0003] Triazole fungicides containing triazole heterocyclic derivatives are attracting attention due to their wide activity on pathogenic fungi of Ascomycota, Basidiomycota and Deuteromycota, and the triazole heterocyclic derivatives also exhibit certain plant growth regulating activity, bringing more possibilities to agricultural production, which makes the triazole fungicide occupy a prominent position in the fungicide market.

[0004] In view of the significant activity of isoxazole insecticides and triazole fungicides in insecticide and fungicide, the isoxazole fragment and the triazole heterocyclic fragment are spliced and modified to synthesize a series of novel pesticides with good insecticidal activity, which is expected to further promote the prevention and control of agricultural pests. SUMMARY

[0005] The purpose of the present application is to provide a phenyl isoxazole derivative containing a triazole ring and a preparation method and application thereof, which is applied as a pesticide active ingredient in the prevention and control of agricultural pests, and shows good insecticidal activity on Plutella xylostella, Spodoptera eridania, Helicoverpa armigera, Ostrinia nubilalis, aphids and other agricultural pests.

[0006] To achieve the above purpose, the present application provides the following technical scheme:

[0007] One of the technical schemes of the present application is:

[0008] A phenyl isoxazole derivative containing a triazole ring has the following structural formula:

[0009]

[0010] In the formula, R 1 , R 2 , R 3 is hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 haloalkoxy;

[0011] R4 halogen, cyano, nitro, C1-C6alkyl or C1-C6haloalkyl;

[0012] R 5 halogen, cyano, nitro, C1-C6alkyl or C1-C6haloalkyl;

[0013] R 6 halogen, cyano, nitro, C1-C6alkyl or C1-C6haloalkyl;

[0014] As preferred, in the formula, R 1 , R 2 , R 3 is hydrogen or chlorine; R 4 is trifluoromethyl; R 5 is cyano; R 6 is acetyl, cycloalkanoyl, methylalkoxalyl, benzoyl or substituted benzoyl.

[0015] As further preferred, in the formula, R 1 , R 3 is chlorine; R 2 is hydrogen or chlorine; R 4 is trifluoromethyl; R 5 is cyano; R 6 is trifluoroacetyl, dichloroacetyl, trichloroacetyl, cycloalkanoyl, methylalkoxalyl, benzoyl, 2-chloro-4-fluorobenzoyl, 3-chloro-3-chlorobenzoyl, 2-trifluoromethylbenzoyl, 3-trifluoromethylbenzoyl, 4-trifluoromethylbenzoyl, 2-fluorobenzoyl, 3-fluorobenzoyl, 4-fluorobenzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 2-methylbenzoyl, 3-methylbenzoyl or 4-methylbenzoyl.

[0016] Typical structures of the phenylisoxazole derivatives containing a triazole ring according to the present application include:

[0017]

[0018]

[0019] The second technical solution of the present application is:

[0020] The preparation method of the above-mentioned phenylisoxazole derivative containing a triazole ring comprises the following steps:

[0021] 1) mixing compound A, hydroxylamine hydrochloride, sodium carbonate and an organic solvent, and reacting to obtain compound B;

[0022] wherein the compound A has a structural formula of the compound B has a structural formula of

[0023] 2) chlorinating the compound B obtained in step 1), and then mixing the chlorination product of the compound B, a compound C, and an organic solvent to react, thereby obtaining a compound D;

[0024] wherein the compound C has a structural formula of the compound D has a structural formula of

[0025] 3) mixing the compound D obtained in step 2), a compound E, a base, and an organic solvent to react, thereby obtaining a compound F;

[0026] wherein the compound E has a structural formula of the compound F has a structural formula of

[0027]

[0028] 4) mixing the compound F obtained in step 3), R 6 and a base to react, thereby obtaining the triazole ring-containing phenyl isoxazole derivative.

[0029] Further, in step 1), the organic solvent is one or more of methanol, ethanol, triethylamine, dichloromethane, chloroform, ethyl acetate, acetonitrile, toluene, xylene, tetrahydrofuran, N,N-dimethylformamide, n-propanol, and water.

[0030] Further, in step 1), the molar ratio of the compound A, hydroxylamine hydrochloride, sodium carbonate, and the organic solvent is 1:(1-3):(1-5):(2-5).

[0031] Further, in step 2), the chlorination reagent is N-chlorosuccinimide.

[0032] Further, in step 2), the organic solvent is one or more of methanol, ethanol, triethylamine, dichloromethane, chloroform, ethyl acetate, acetonitrile, toluene, xylene, tetrahydrofuran, N,N-dimethylformamide, n-propanol, and water.

[0033] Further, in step 2), the molar ratio of the compound B, the chlorination reagent, the compound C, and the organic solvent is 1:(1-4):(1-3):(2-8).

[0034] Further, in step 3), the base is lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, potassium tert-butoxide, aqueous ammonia, methylamine, ethylamine, propylamine, dimethylamine, diethylamine, dipropylamine, trimethylamine, triethylamine, tripropylamine, N,N-diisopropylethylamine, sodium acetate, potassium acetate or sodium bicarbonate.

[0035] Further, in step 3), the organic solvent is one or more of methanol, ethanol, triethylamine, dichloromethane, chloroform, ethyl acetate, acetonitrile, toluene, xylene, tetrahydrofuran, N,N-dimethylformamide, n-propanol and water.

[0036] Further, in step 3), the molar ratio of the compound D, the compound E, the base and the organic solvent is 1:(1-4):(1-3):(2-8).

[0037] Further, in step 3), the compound E can also be

[0038] Further, when the compound E is a reducing agent is further added to reduce -NO2 to -NH2 after the reaction of the compound D, the base and the organic solvent is completed.

[0039] Further, the reducing agent is one of Na, K, Mg, Al, Zn, Fe, Cu, LiAl H4, NaBH4, H2S, Na2SO3, H2C2O4, Na2S2O4 and N2H4; and the molar ratio of the compound D, the reducing agent, the compound E, the base and the organic solvent is 1:(1-4):(1-4):(1-3):(2-8).

[0040] Further, in step 4), the base is lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, potassium tert-butoxide, aqueous ammonia, methylamine, ethylamine, propylamine, dimethylamine, diethylamine, dipropylamine, trimethylamine, triethylamine, tripropylamine, N,N-diisopropylethylamine, sodium acetate, potassium acetate or sodium bicarbonate.

[0041] Further, in step 4), the molar ratio of the compound F, R 6 and the base is 1:(1-4):(1-3).

[0042] The synthetic route of the preparation method of the phenyl isoxazole derivative containing a triazole ring according to the present application is shown as follows:

[0043]

[0044] The third technical solution of the present application is:

[0045] The application relates to application of a phenyl isoxazole derivative containing a triazole ring as a pesticide active ingredient in the prevention and treatment of agricultural pests.

[0046] Further, the agricultural pests include Plutella xylostella, Spodoptera littoralis, Helicoverpa armigera, Ostrinia nubilalis and aphids.

[0047] Compared with the prior art, the application has the beneficial effects that:

[0048] The phenyl isoxazole derivative containing a triazole ring provided by the application has good insecticidal activity on Plutella xylostella, Spodoptera littoralis, Helicoverpa armigera, Ostrinia nubilalis and aphids when the concentration is 50 mu g / mL, and therefore, the phenyl isoxazole derivative containing a triazole ring provided by the application can be applied to the prevention and treatment of agricultural pests as a pesticide active ingredient. DETAILED DESCRIPTION

[0049] The various exemplary embodiments of the present application will now be described in detail below, which should not be considered as limiting the present application, but should be understood as a more detailed description of certain aspects, characteristics and embodiments of the present application. It should be understood that the terms described in the present application are only for describing the particular embodiments, and are not used to limit the present application.

[0050] In addition, for the numerical range in the present application, it should be understood that each intermediate value between the upper limit and the lower limit of the range is also specifically disclosed. Each smaller range between any stated value or stated range and any other stated value or intermediate value in the stated range is also included in the present application. The upper limit and the lower limit of these smaller ranges can be independently included or excluded from the range.

[0051] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present application, the preferred methods and materials are described. All documents mentioned in this specification are incorporated by reference to disclose and describe the methods and / or materials in connection with which the documents are cited. In case of conflict between the content of the specification and that of any document incorporated herein by reference, the content of the specification prevails.

[0052] Various modifications and changes can be made to the specific embodiments of the present application described in this specification without departing from the scope or spirit of the application. Other embodiments of the application will be apparent to those skilled in the art from consideration of the specification and practice of the application disclosed herein. The specification and examples given are exemplary only.

[0053] As used herein, the terms "comprise", "comprising", "including", "include", "contain", "containing", "have", "having" or variants thereof are open-ended, and include the stated integer or group, but also any other integer or group.

[0054] Example 1

[0055] A phenyl isoxazole derivative containing a triazole ring

[0056] 1) 3-cyano-4-fluorobenzaldehyde (Compound A, 20.0 g, 0.13 mol), hydroxylamine hydrochloride (14 g, 0.2 mol) and methanol-water solution (250 mL, 1 mol:2 mol) were added to a 250 mL round bottom flask and stirred at room temperature for 2 h, after which sodium carbonate (25 g, 0.23 mol) was slowly added and stirred at room temperature for a further 2 h, after which the reaction was completed, ice was added to precipitate the solid, suction filtered, dried, and purified by column chromatography to obtain a yellow-green solid (E)-2-fluoro-5-(hydroxyimino)methylbenzonitrile (Compound B);

[0057]

[0058] The yield of Compound B was 82% as detected;

[0059] 2) (E)-2-fluoro-5-(hydroxyimino)methylbenzonitrile (Compound B, 16.4 g, 0.11 mol) and NCS (30 g, 0.22 mol) obtained in Step 1) were added to a 250 mL round bottom flask and stirred at room temperature for 30 min, after which 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (Compound C, 28.8 g, 0.12 mol) and triethylamine (13.3 g, 0.13 mol) were added and stirred at room temperature for 18 h, after which the reaction was completed, washed with water, extracted with dichloromethane, dried with anhydrous sodium sulfate, concentrated in vacuo, and purified by column chromatography to obtain a white solid 5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-fluorobenzonitrile (Compound D);

[0060]

[0061] The yield of Compound D was 95.7% as detected;

[0062] 3) 3-amino-1,2,4-triazole (compound E, 1.7 g, 20 mmol), potassium tert-butoxide (2.8 g, 2.5 mmol) and DMF (50 mL) were added to a 100 mL round bottom flask, stirred at room temperature for 1 h, then 5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-fluorobenzonitrile (compound D, 4 g, 10 mmol) obtained in step 2) was slowly added, stirred at 100 °C for 4 h, after the reaction was completed, concentrated under vacuum, purified by column chromatography to obtain 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)benzonitrile (compound F) as a light yellow solid;

[0063]

[0064] The yield of compound F was 44% as detected;

[0065] 4) 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)benzonitrile (compound F, 0.3 g, 0.64 mmol) obtained in step 3), methyl 2-chloro-2-oxoacetate (0.08 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) were added to a 50 mL round bottom flask, stirred at 120 °C for 4 h, after the reaction was completed, concentrated under vacuum, purified by column chromatography to obtain methyl 2-((1-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)amino)-2-oxoacetate, i.e. the triazol ring-containing phenyl isoxazole derivative as a light yellow solid;

[0066]

[0067] The yield of the triazol ring-containing phenyl isoxazole derivative was 16% as detected.

[0068] 1 HNMR (500 MHz,) δ 9.88 (s, 1H), 8.64 (s, 1H), 7.93 (s, 1H), 7.92-7.88 (m, 2H), 7.46 (s, 2H), 7.41 (d, J = 0.9 Hz, 1H), 4.75 (d, J = 13.8 Hz, 1H), 4.66 (s, 3H), 4.46 (d, J = 13.8 Hz, 1H).

[0069] Example 2

[0070] A triazol ring-containing phenyl isoxazole derivative

[0071] Steps 1) to 3) are the same as in Example 1.

[0072] 4) 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)phenyl cyanide (Compound F, 0.3 g, 0.64 mmol) obtained in Step 3), trifluoroacetyl chloride (0.12 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol), and dichloroethane (20 mL) were added to a 50 mL round-bottom flask, and the reaction was stirred at 120°C under reflux for 4 h. After the reaction was completed, it was concentrated in vacuo, and purified by column chromatography to obtain N-(1-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-2,2,2-trifluoroacetamide as a light brown solid, which is the triazol ring-containing phenyl isoxazole derivative.

[0073]

[0074] The yield of the triazol ring-containing phenyl isoxazole derivative was 13.3% as a result of the test.

[0075] 1 HNMR (600 MHz,) δ 8.35 (s, 1H), 8.08 (s, 1H), 7.47 (d, J = 1.4 Hz, 1H), 7.45 (dd, J = 6.9, 1.4 Hz, 1H), 7.43 (d, J = 6.9 Hz, 1H), 7.00 (s, 2H), 6.96 - 6.95 (m, 1H), 4.28 (d, J = 13.7 Hz, 1H), 3.99 (d, J = 13.7 Hz, 1H).

[0076] Example 3

[0077] A triazol ring-containing phenyl isoxazole derivative

[0078] Steps 1) to 3) are the same as in Example 1.

[0079] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), dichloroacetyl chloride (0.1 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-2,2-dichloroacetamide as a brown solid, which is the triazol ring containing phenyl isoxazole derivative;

[0080]

[0081] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 12.5%.

[0082] 1 H NMR (500 MHz, DMSO-d6) δ 8.52 (s, 1H), 8.27 (s, 1H), 7.68 - 7.63 (m, 2H), 7.61 (d, J = 6.9 Hz, 1H), 7.19 (s, 2H), 7.16 (t, J = 1.3 Hz, 1H), 6.08 (s, 1H), 4.48 (d, J = 13.8 Hz, 1H), 4.19 (d, J = 13.8 Hz, 1H).

[0083] Example 4

[0084] A triazol ring containing phenyl isoxazole derivative

[0085] Steps 1) to 3) are same as example 1;

[0086] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), trichloroacetyl chloride (0.1 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-2,2,2-trichloroacetamide as a white solid, which is the triazol ring containing phenyl isoxazole derivative;

[0087]

[0088] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 41.7%.

[0089] 1 HNMR (500 MHz,) δ 8.55 (s, 1H), 8.29 (s, 1H), 7.67 (s, 1H), 7.66 - 7.61 (m, 2H), 7.20 (s, 2H), 7.16 (d, J = 1.3 Hz, 1H), 4.49 (d, J = 13.8 Hz, 1H), 4.19 (d, J = 13.8 Hz, 1H).

[0090] Example 5

[0091] A triazol ring containing phenyl isoxazole derivative

[0092] Steps 1) to 3) are same as example 1;

[0093] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), benzoyl chloride (0.09 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred under reflux at 120 °C for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)benzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0094]

[0095] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 50%.

[0096] 1 HNMR (500 MHz,) δ 9.40 (s, 1H), 8.04 (s, 1H), 7.64 (s, 1H), 7.55 (dd, J = 10.5, 4.7 Hz, 4H), 7.24 (t, J = 5.9 Hz, 1H), 7.20 - 7.17 (m, 4H), 7.12 (t, J = 1.5 Hz, 1H), 4.49 (d, J = 13.8 Hz, 1H), 4.22 (d, J = 13.9 Hz, 1H).

[0097] Example 6

[0098] A triazol ring containing phenyl isoxazole derivative

[0099] Steps 1) to 3) are same as example 1;

[0100] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 2-chloro-4- fluorobenzoyl chloride (0.12 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-2-chloro-4-fluorobenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0101]

[0102] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 50%.

[0103] 1 HNMR (500 MHz,) δ 9.76 (s, 1H), 7.97 (s, 1H), 7.67 (s, 1H), 7.62 - 7.57 (m, 2H), 7.40 - 7.34 (m, 1H), 7.17 (s, 2H), 7.12 (d, J = 0.7 Hz, 1H), 6.97 - 6.92 (m, 1H), 6.88 (dd, J = 9.2, 3.8 Hz, 1H), 4.49 (d, J = 13.9 Hz, 1H), 4.24 (d, J = 13.9 Hz, 1H).

[0104] Example 7

[0105] A triazol ring containing phenyl isoxazole derivative

[0106] Steps 1) to 3) are same as in example 1;

[0107] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 3,5- dichlorobenzoyl chloride (0.13 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-3,5-dichlorobenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0108]

[0109] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 33.3%.

[0110] 1 HNMR (600 MHz,) δ 9.08 (s, 1H), 8.80 (s, 1H), 8.10 - 8.08 (m, 1H), 8.07 - 8.03 (m, 2H), 7.83 (d, J = 1.9 Hz, 2H), 7.58 (t, J = 1.8 Hz, 1H), 7.51 (d, J = 1.6 Hz, 2H), 7.46 (dd, J = 2.4, 1.2 Hz, 1H), 4.12 (d, J = 17.1 Hz, 1H), 3.75 (d, J = 17.2 Hz, 1H).

[0111] Example 8

[0112] A triazol ring containing phenyl isoxazole derivative

[0113] Steps 1) to 3) are same as in example 1;

[0114] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (compound F, 0.3 g, 0.64 mmol), 2- trifluoromethylbenzoyl chloride (0.13 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred under reflux at 120 °C for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-2-trifluoromethylbenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0115]

[0116] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 26.7%.

[0117] 1 HNMR (500 MHz,) δ 9.83 (s, 1H), 7.67 (s, 1H), 7.58 (t, J = 18.9 Hz, 3H), 7.43 (d, J = 6.1 Hz, 1H), 7.40 - 7.30 (m, 3H), 7.18 (s, 2H), 7.13 (s, 1H), 4.49 (d, J = 13.8 Hz, 1H), 4.22 (d, J = 13.8 Hz, 1H).

[0118] Example 9

[0119] A triazol ring containing phenyl isoxazole derivative

[0120] Steps 1) to 3) are same as example 1;

[0121] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (compound F, 0.3 g, 0.64 mmol), 3- trifluoromethylbenzoyl chloride (0.13 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to get N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-3-trifluoromethylbenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0122]

[0123] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 76.7%.

[0124] 1 HNMR (600 MHz,) δ 9.50 (s, 1H), 8.84 (s, 1H), 8.29 (s, 1H), 8.21 (d, J = 7.8 Hz, 1H), 8.11 - 8.08 (m, 2H), 8.06 (dd, J = 8.7, 1.9 Hz, 1H), 7.87 (d, J = 7.8 Hz, 1H), 7.69 (t, J = 7.8 Hz, 1H), 7.51 (d, J = 1.6 Hz, 2H), 7.46 (t, J = 1.8 Hz, 1H), 4.12 (d, J = 17.1 Hz, 1H), 3.75 (d, J = 17.2 Hz, 1H).

[0125] Example 10

[0126] A triazol ring containing phenyl isoxazole derivative

[0127] Steps 1) to 3) are same as example 1;

[0128] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (compound F, 0.3 g, 0.64 mmol), 4- trifluoromethylbenzoyl chloride (0.13 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-4-trifluoromethylbenzamide as a white solid, which is the triazol ring containing phenyl isoxazole derivative;

[0129]

[0130] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 53.3%.

[0131] 1 HNMR (600 MHz,) δ 8.98 (s, 1H), 8.81 (s, 1H), 8.09 (d, J = 0.9 Hz, 2H), 8.08 (td, J = 4.4, 1.1 Hz, 3H), 7.80 (d, J = 8.3 Hz, 2H), 7.51 (d, J = 1.6 Hz, 2H), 7.46 (t, J = 1.8 Hz, 1H), 4.12 (d, J = 17.2 Hz, 1H), 3.75 (d, J = 17.2 Hz, 1H).

[0132] Example 11

[0133] A triazol ring containing phenyl isoxazole derivative

[0134] Steps 1) to 3) are same as example 1;

[0135] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 2- fluorobenzoyl chloride (0.1 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-2-fluorobenzamide as a yellowish solid, which is the triazol ring containing phenyl isoxazole derivative;

[0136]

[0137] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 72.5%.

[0138] 1 HNMR (400 MHz, CDC13) δ 9.31 (s, 2H), 9.31 (s, 1H), 8.87 (s, 2H), 8.87 (s, 2H), 8.22 (t, J = 7.4 Hz, 2H), 8.11 (d, J = 8.9 Hz, 4H), 8.08 - 8.03 (m, 2H), 7.61 - 7.55 (m, 2H), 7.52 (s, 3H), 7.46 (s, 2H), 7.35 (t, J = 7.5 Hz, 2H), 7.27 (s, 2H), 4.13 (d, J = 17.2 Hz, 2H), 4.13 (d, J = 17.2 Hz, 2H), 3.76 (d, J = 17.3 Hz, 2H), 3.76 (d, J = 17.3 Hz, 2H).

[0139] Example 12

[0140] A triazol ring containing phenyl isoxazole derivative

[0141] Steps 1) to 3) are same as in example 1;

[0142] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (compound F, 0.3 g, 0.64 mmol), 3- fluorobenzoyl chloride (0.1 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-3-fluorobenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0143]

[0144] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 33.3%.

[0145] 1 HNMR (400 MHz, CDC13) δ 10.44 (s, 1H), 8.90 (s, 1H), 8.11 (d, J = 7.8 Hz, 2H), 8.04 (d, J = 8.6 Hz, 1H), 7.89 (t, J = 8.8 Hz, 2H), 7.80 (dd, J = 18.3, 9.2 Hz, 2H), 7.52 (d, J = 5.4 Hz, 2H), 7.45 (s, 1H), 4.13 (d, J = 17.3 Hz, 1H), 3.77 (d, J = 17.3 Hz, 1H).

[0146] Example 13

[0147] A triazol ring containing phenyl isoxazole derivative

[0148] Steps 1) to 3) are same as example 1;

[0149] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 4- fluorobenzoyl chloride (0.1 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-4-fluorobenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0150]

[0151] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 45.5%.

[0152] 1 HNMR (400 MHz, CDC13) δ 10.46 (s, 1H), 8.91 (s, 1H), 8.13 (d, J = 8.4 Hz, 3H), 8.05 (d, J = 9.6 Hz, 1H), 7.51 (s, 1H), 7.47 - 7.43 (m, 1H), 7.21 (t, J = 8.5 Hz, 1H), 7.18 - 7.08 (m, 3H), 4.13 (d, J = 17.3 Hz, 1H), 3.77 (d, J = 17.2 Hz, 1H).

[0153] Example 14

[0154] A triazol ring containing phenyl isoxazole derivative

[0155] Steps 1) to 3) are same as example 1;

[0156] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 2- chlorobenzoyl chloride (0.11 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-2-chlorobenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0157]

[0158] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 62%.

[0159] 1 HNMR (600 MHz,) δ 9.31 (s, 1H), 7.64 (s, 1H), 7.46 (s, 1H), 7.40 (dd, J = 6.9, 1.3 Hz, 1H), 7.17 (d, J = 5.8 Hz, 1H), 6.99 (s, 2H), 6.98 - 6.95 (m, 2H), 6.93 (ddd, J = 6.8, 4.4, 1.3 Hz, 2H), 4.29 (d, J = 13.8 Hz, 1H), 4.01 (d, J = 13.8 Hz, 1H).

[0160] Example 15

[0161] A triazol ring containing phenyl isoxazole derivative

[0162] Steps 1) to 3) are same as in example 1;

[0163] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 3- chlorobenzoyl chloride (0.11 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-3-chlorobenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0164]

[0165] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 47.5%.

[0166] 1 HNMR (600 MHz,) δ 9.90 (s, 1H), 8.57 (s, 1H), 7.95 (t, J = 1.2 Hz, 1H), 7.93 (d, J = 1.7 Hz, 1H), 7.92 (d, J = 2.6 Hz, 1H), 7.87 (dd, J = 7.0, 1.5 Hz, 1H), 7.84 (t, J = 6.9 Hz, 2H), 7.51 - 7.50 (m, 1H), 7.45 (t, J = 4.9 Hz, 2H), 7.43 - 7.41 (m, 1H), 7.39 (t, J = 6.3 Hz, 1H), 4.75 (d, J = 13.7 Hz, 1H), 4.46 (d, J = 13.7 Hz, 1H).

[0167] Example 16

[0168] A triazol ring containing phenyl isoxazole derivative

[0169] Steps 1) to 3) are same as in example 1;

[0170] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (compound F, 0.3 g, 0.64 mmol), 4- chlorobenzoyl chloride (0.11 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-4-chlorobenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0171]

[0172] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 52%.

[0173] 1 H NMR (500 MHz, DMSO-d6) δ 9.99 (s, 1H), 8.36 (s, 1H), 7.66 (d, J = 1.6 Hz, 1H), 7.58 (dd, J = 6.9, 1.5 Hz, 1H), 7.40 (dd, J = 9.3, 4.1 Hz, 3H), 7.24 (t, J = 1.4 Hz, 1H), 7.06 (dd, J = 7.0, 1.3 Hz, 4H), 4.60 (d, J = 14.7 Hz, 1H), 4.51 (d, J = 14.8 Hz, 1H).

[0174] Example 17

[0175] A triazol ring containing phenyl isoxazole derivative

[0176] Steps 1) to 3) are same as example 1;

[0177] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 2- methylbenzoyl chloride (0.1 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-2-methylbenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0178]

[0179] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 42%.

[0180] 1 HNMR (600 MHz,) δ 9.19 (s, 1H), 8.28 (s, 1H), 7.94 (d, J = 6.9 Hz, 1H), 7.92 (d, J = 1.4 Hz, 1H), 7.88 (dd, J = 6.9, 1.6 Hz, 2H), 7.54 (d, J = 5.9 Hz, 1H), 7.46 (s, 2H), 7.42 (dd, J = 3.2, 1.8 Hz, 1H), 7.41 - 7.37 (m, 2H), 4.75 (s, J = 13.7 Hz, 1H), 4.45 (d, J = 13.7 Hz, 1H), 3.50 (s, 3H).

[0181] Example 18

[0182] A triazol ring containing phenyl isoxazole derivative

[0183] Steps 1) to 3) are same as example 1;

[0184] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 3- methylbenzoyl chloride (0.1 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-3-methylbenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0185]

[0186] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 58.6%.

[0187] 1 HNMR (600 MHz,) δ 8.65 (s, 1H), 8.04 (s, 1H), 7.47 (dd, J = 6.3, 4.2 Hz, 2H), 7.41 (dd, J = 6.9, 1.3 Hz, 2H), 7.25 (s, 1H), 7.22 (dd, J = 4.5, 2.3 Hz, 1H), 6.99 (d, J = 0.8 Hz, 2H), 6.95 (t, J = 1.3 Hz, 1H), 6.91 (d, J = 3.9 Hz, 2H), 4.28 (d, J = 13.7 Hz, 1H), 4.00 (d, J = 13.7 Hz, 1H), 2.95 (s, 3H).

[0188] Example 19

[0189] A triazol ring containing phenyl isoxazole derivative

[0190] Steps 1) to 3) are same as in example 1;

[0191] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 4- methylbenzoyl chloride (0.1 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-4-methylbenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0192]

[0193] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 21.6%.

[0194] 1 HNMR (600 MHz,) δ 8.84 (s, 1H), 8.09 (s, 1H), 7.50 (d, J = 7.0 Hz, 1H), 7.47 (d, J = 1.5 Hz, 1H), 7.41 (dd, J = 6.7, 1.5 Hz, 1H), 7.39 (d, J = 6.5 Hz, 2H), 7.35 (d, J = 6.4 Hz, 2H), 7.00 (d, J = 0.8 Hz, 2H), 6.95 (t, J = 1.3 Hz, 1H), 4.28 (d, J = 13.7 Hz, 1H), 3.99 (d, J = 13.7 Hz, 1H), 2.94 (s, 3H).

[0195] Example 20

[0196] A triazol ring containing phenyl isoxazole derivative

[0197] Step 1) is same as example 1;

[0198] 2) (E)-2-fluoro-5-(hydroxyimino)methylbenzonitrile (Compound B, 16.4 g, 0.11 mol) and NCS (30 g, 0.22 mol) obtained from step 1) were added to a 250 mL round bottom flask and stirred at room temperature for 30 min, after which 1,2,3-trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (28.8 g, 0.12 mol) and triethylamine (13.3 g, 0.13 mol) were added and stirred at room temperature for 18 h. After completion of the reaction, it was washed with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, concentrated under vacuum and purified by column chromatography to obtain 5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-fluorobenzonitrile (Compound D) as a white solid;

[0199]

[0200] The yield of Compound D was found to be 88.4%;

[0201] 3) 3-amino-1,2,4-triazole (Compound E, 1.7 g, 20 mmol), potassium tert-butoxide (2.8 g, 2.5 mmol) and DMF (50 mL) were added to a 100 mL round bottom flask and stirred at room temperature for 1 h, after which 5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-fluorobenzonitrile (Compound D, 4 g, 10 mmol) obtained from step 2) was added slowly and stirred at 100 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F) as a light yellow solid;

[0202]

[0203] The yield of Compound F was found to be 52%;

[0204] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,4,5-trichlorophenyl)-5- (trifluoromethyl)-4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 2-fluorobenzoyl chloride (0.09 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,4,5-trichlorophenyl)-5- (trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-2- fluorobenzamide as a white solid, which is the triazol ring containing phenyl isoxazole derivative;

[0205]

[0206] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 42%.

[0207] 1 HNMR (600 MHz,) δ 9.33 (d, J = 13.8 Hz, 1H), 8.83 (s, 1H), 8.16 (td, J = 7.8, 1.7 Hz, 1H), 8.09 - 8.02 (m, 2H), 7.64 (s, 2H), 7.59 - 7.54 (m, 1H), 7.35 - 7.30 (m, 1H), 7.21 (dd, J = 11.8, 8.5 Hz, 1H), 4.13 (d, J = 17.2 Hz, 1H), 3.78 (d, J = 17.2 Hz, 1H).

[0208] Example 21

[0209] A triazol ring containing phenyl isoxazole derivative

[0210] Steps 1) to 3) are same as in example 20;

[0211] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 3- fluorobenzoyl chloride (0.09 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-3-fluorobenzamide as a white solid, which is the triazol ring containing phenyl isoxazole derivative;

[0212]

[0213] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 42%.

[0214] 1 HNMR (600 MHz,) δ 9.10 (s, 1H), 8.00 (s, 1H), 7.46 (d, J = 1.2 Hz, 1H), 7.43 - 7.39 (m, 2H), 7.23 (d, J = 6.2 Hz, 1H), 7.18 - 7.16 (m, 1H), 7.10 (s, 2H), 6.99 (td, J = 6.4, 4.5 Hz, 1H), 6.82 (td, J = 6.7, 1.8 Hz, 1H), 4.29 (d, J = 13.8 Hz, 1H), 4.01 (d, J = 13.8 Hz, 1H).

[0215] Example 22

[0216] A triazol ring containing phenyl isoxazole derivative

[0217] Steps 1) to 3) are same as in example 20;

[0218] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,4,5-trichlorophenyl)-5- (trifluoromethyl)-4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 4-fluorobenzoyl chloride (0.09 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,4,5-trichlorophenyl)-5- (trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-4- fluorobenzamide as a white solid, which is the triazol ring containing phenyl isoxazole derivative;

[0219]

[0220] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 35.6%.

[0221] 1 HNMR (600 MHz,) δ 9.94 (s, 1H), 8.35 (s, 1H), 7.65 (d, J = 1.5 Hz, 1H), 7.57 (dd, J = 6.9, 1.5 Hz, 1H), 7.45 - 7.43 (m, 2H), 7.40 (d, J = 6.9 Hz, 1H), 7.23 (s, 2H), 6.86 (t, J = 7.0 Hz, 2H), 4.59 (d, J = 14.7 Hz, 1H), 4.52 (d, J = 14.7 Hz, 1H).

[0222] Example 23

[0223] A triazol ring containing phenyl isoxazole derivative

[0224] Steps 1) to 2) are same as in example 20;

[0225] 3) 3-nitro-1,2,4-triazole (compound E, 1.7 g, 20 mmol), potassium tert-butoxide (2.8 g, 2.5 mmol) and DMF (50 mL) were added to a 100 mL round bottom flask, stirred at room temperature for 1 h, then 5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2- fluorobenzonitrile (compound D, 4 g, 10 mmol) obtained in step 2) was slowly added, stirred at 100 °C for 4 h, then Fe powder (11 g, 20 mmol) was added, stirred at 100 °C for 2 h, after the reaction was completed, vacuum concentration, column chromatography purification, to obtain 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,4,5-trichlorophenyl)-5- (trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl nitrile (compound F) as a light yellow solid;

[0226]

[0227] The yield of compound F was 61% as detected;

[0228] 4) 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl nitrile (compound F, 0.3 g, 0.64 mmol) obtained in step 3), 2-chlorobenzoyl chloride (0.09 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) were added to a 50 mL round bottom flask, stirred at 120 °C for 4 h, after the reaction was completed, vacuum concentration, column chromatography purification, to obtain N-(1-(2-cyano-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-2-chlorobenzamide, i.e. the phenyl isoxazole derivative containing a triazole ring, as a white solid;

[0229]

[0230] The yield of the phenyl isoxazole derivative containing a triazole ring was 57% as detected.

[0231] 1HNMR (500 MHz, DMSO-d6) δ 10.10 (s, 1H), 8.32 (s, 1H), 7.65 (d, J = 1.4 Hz, 1H), 7.57 (dd, J = 6.9, 1.4 Hz, 1H), 7.25 (d, J = 15.2 Hz, 3H), 7.21 - 7.18 (m, 1H), 7.01 - 6.99 (m, 2H), 6.96 - 6.94 (m, 1H), 4.60 (d, J = 14.7 Hz, 1H), 4.52 (d, J = 14.8 Hz, 1H).

[0232] Example 24

[0233] A phenyl isoxazole derivative containing a triazole ring

[0234] Steps 1) to 3) are the same as in Example 23.

[0235] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)phenyl cyanide (Compound F, 0.3 g, 0.64 mmol), 3- chlorobenzoyl chloride (0.09 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) were added to a 50 mL round bottom flask, and stirred at 120 °C under reflux for 4 h. After the reaction was completed, it was concentrated under vacuum, and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-3-chlorobenzamide, which is the phenyl isoxazole derivative containing a triazole ring;

[0236]

[0237] The yield of the phenyl isoxazole derivative containing a triazole ring was 34.6%.

[0238] 1 HNMR (500 MHz, DMSO-d6) δ 10.06 (s, 1H), 8.38 (s, 1H), 7.68 (d, J = 1.5 Hz, 1H), 7.60 (dd, J = 6.9, 1.7 Hz, 1H), 7.43 (t, J = 4.3 Hz, 2H), 7.38 - 7.35 (m, 1H), 7.26 (s, 2H), 7.16 - 7.13 (m, 1H), 7.05 (t, J = 6.3 Hz, 1H), 4.62 (d, J = 14.7 Hz, 1H), 4.55 (d, J = 14.8 Hz, 1H).

[0239] Example 25

[0240] A phenyl isoxazole derivative containing a triazole ring

[0241] Steps 1) to 3) are the same as in Example 23;

[0242] 4) 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)phenyl cyanide (Compound F, 0.3 g, 0.64 mmol) obtained in Step 3), 4-chlorobenzoyl chloride (0.093 g, 0.6 mmol), triethylamine (0.1 g, 0.96 mmol), and dichloroethane (20 mL) were added to a 50 mL round-bottom flask, and the reaction was stirred at 120°C under reflux for 4 h. After the reaction was completed, it was concentrated in vacuo, and purified by column chromatography to obtain N-(1-(2-cyano-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-4-chlorobenzamide, which is the phenyl isoxazole derivative containing a triazole ring;

[0243]

[0244] The yield of the phenyl isoxazole derivative containing a triazole ring was 52% as a result of the test.

[0245] 1 HNMR (500 MHz,) δ 10.00 (s, 1H), 8.36 (s, 1H), 7.65 (d, J = 1.6 Hz, 1H), 7.57 (dd, J = 6.9, 1.6 Hz, 1H), 7.42 - 7.38 (m, 3H), 7.24 (s, 2H), 7.07 - 7.04 (m, 2H), 4.60 (d, J = 14.7 Hz, 1H), 4.52 (d, J = 14.8 Hz, 1H).

[0246] Example 26

[0247] A phenyl isoxazole derivative containing a triazole ring

[0248] Steps 1) to 3) are the same as in Example 23;

[0249] 4) 2-(5-amino-lH-l,2,4-triazol-l-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 2- methylbenzoyl chloride (0.093 g, 0.6 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) obtained from step 3) were taken in a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After completion of the reaction, it was concentrated under vacuum and purified by column chromatography to obtain N-(l-(2-cyano-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-lH-l,2,4-triazol-5-yl)-2-methylbenzamide as a light yellow solid, which is the triazol ring containing phenyl isoxazole derivative;

[0250]

[0251] The yield of the triazol ring containing phenyl isoxazole derivative was found to be 44.8%.

[0252] 1 H NMR (400 MHz, CDC13) δ 10.40 (s, 1H), 8.11 (s, 1H), 8.09 (d, J = 1.9 Hz, 1H), 8.06 (s, 1H), 8.01 (dd, J = 8.7, 1.9 Hz, 1H), 7.65 (s, 2H), 7.60 (d, J = 7.1 Hz, 1H), 7.47 - 7.40 (m, 1H), 7.34 (t, J = 7.0 Hz, 2H), 4.13 (d, J = 17.2 Hz, 1H), 3.76 (d, J = 17.3 Hz, 1H), 2.54 (s, 3H).

[0253] Example 27

[0254] A triazol ring containing phenyl isoxazole derivative

[0255] Steps 1) to 3) are same as in example 23;

[0256] 4) 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydroisoxazol-3-yl)benzonitrile (Compound F, 0.3 g, 0.64 mmol), 3- methylbenzoyl chloride (0.093 g, 0.6 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) were added to a 50 mL round bottom flask and stirred at 120 °C under reflux for 4 h. After the reaction was completed, it was concentrated under vacuum and purified by column chromatography to obtain N-(1-(2-cyano-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-3-methylbenzamide, i.e. the triazol ring-containing phenylisoxazole derivative;

[0257]

[0258] The yield of the triazol ring-containing phenylisoxazole derivative was 51.5%.

[0259] 1 H NMR (400 MHz, CDC13) δ 9.62 (s, 1H), 8.70 (s, 1H), 8.09 (d, J = 1.7 Hz, 1H), 8.03 (dt, J = 8.7, 5.2 Hz, 2H), 7.76 (dd, J = 9.0, 4.7 Hz, 2H), 7.64 (s, 2H), 7.40 (d, J = 4.7 Hz, 2H), 4.14 (d, J = 17.3 Hz, 1H), 3.79 (d, J = 17.3 Hz, 1H), 2.43 (s, 3H).

[0260] Effect verification

[0261] I. Insecticidal activity test on Plutella xylostella

[0262] Fresh cabbage was immersed in a solution of the compound to be tested (the triazol ring-containing phenylisoxazole derivative prepared in Examples 1 to 27) at a concentration of 50 μg / mL, air-dried after 30 seconds, and placed in a culture dish lined with filter paper, and then 15 three-instar Plutella xylostella were transferred to the culture dish, and incubated in an incubator at 26 °C, 85% relative humidity, light / dark = 16 / 8, for 2 days. After the incubation, the mortality of Plutella xylostella was evaluated (the larvae were gently touched, and those that could not crawl normally were determined to be dead), and the test was performed in triplicate.

[0263]

[0264] wherein X is the number of live insects before incubation, and Y is the number of live insects after incubation.

[0265] The results of the insecticidal activity detection of the triazole ring-containing phenyl isoxazole derivatives prepared in Examples 1-27 on Plutella xylostella are shown in Table 1.

[0266] Table 1 Results of the insecticidal activity detection of the triazole ring-containing phenyl isoxazole derivatives on Plutella xylostella

[0267]

[0268] As shown in Table 1, the triazole ring-containing phenyl isoxazole derivatives provided by the application have a mortality rate of 100% on Plutella xylostella at a concentration of 50 μg / mL, which is comparable to that of flucycloxuron, indicating that the triazole ring-containing phenyl isoxazole derivatives provided by the application have certain insecticidal activity on Plutella xylostella and can be applied to the prevention and control of agricultural pests as active ingredients of pesticides.

[0269] II. Insecticidal activity detection on Helicoverpa armigera

[0270] The solution of the compound to be detected (the triazole ring-containing phenyl isoxazole derivatives prepared in Examples 1-27) at a concentration of 50 μg / mL was added to a 24-well plate, and 24 three-instar Helicoverpa armigera were added to each well. The plate was cultured in an incubator at 26°C and 85% relative humidity, with light / darkness = 16 / 8, for 2 days. After the culture, the mortality rate of Helicoverpa armigera was evaluated (the larvae were determined to be dead if they could not crawl normally), and the detection was performed in triplicate.

[0271]

[0272] Wherein, X is the number of live insects before culture, and Y is the number of live insects after culture.

[0273] The results of the insecticidal activity detection of the triazole ring-containing phenyl isoxazole derivatives prepared in Examples 1-27 on Helicoverpa armigera are shown in Table 2.

[0274] Table 2 Results of the insecticidal activity detection of the triazole ring-containing phenyl isoxazole derivatives on Helicoverpa armigera

[0275]

[0276] As shown in Table 2, the triazole ring-containing phenyl isoxazole derivatives provided by the application have a mortality rate of 100% on Helicoverpa armigera at a concentration of 50 μg / mL, which is comparable to that of flucycloxuron, indicating that the triazole ring-containing phenyl isoxazole derivatives provided by the application have certain insecticidal activity on Helicoverpa armigera and can be applied to the prevention and control of agricultural pests as active ingredients of pesticides.

[0277] III. Insecticidal activity detection on Helicoverpa armigera

[0278] The solution of the compound to be detected (the phenyl isoxazole derivative containing a triazole ring prepared in Examples 1-27) with a concentration of 50 μg / mL was added to a 24-well plate, and 24 three-instar cotton bollworms were added to each well. The plate was cultured in a culture box at 26°C and 85% relative humidity, with light / darkness = 16 / 8, for 2 days. After the culture, the mortality of the cotton bollworms was evaluated (the larvae were determined to be dead if they could not crawl normally), and the test was performed in triplicate.

[0279]

[0280] wherein X represents the number of living insects before culture, and Y represents the number of living insects after culture.

[0281] The results of the insecticidal activity detection of the phenyl isoxazole derivative containing a triazole ring prepared in Examples 1-27 on cotton bollworms are shown in Table 3.

[0282] Table 3 Results of insecticidal activity detection of the phenyl isoxazole derivative containing a triazole ring on cotton bollworms

[0283]

[0284] As shown in Table 3, the phenyl isoxazole derivative containing a triazole ring provided in the application has a mortality rate of 100% on cotton bollworms when the concentration is 50 μg / mL, which is equivalent to that of fluoxastrodamide. This indicates that the phenyl isoxazole derivative containing a triazole ring provided in the application has certain insecticidal activity on cotton bollworms and can be applied to the prevention and control of agricultural pests as an active ingredient of a pesticide.

[0285] IV. Insecticidal activity detection on corn borer

[0286] The solution of the compound to be detected (the phenyl isoxazole derivative containing a triazole ring prepared in Examples 1-27) with a concentration of 50 μg / mL was added to a 24-well plate, and 24 three-instar corn borers were added to each well. The plate was cultured in a culture box at 26°C and 85% relative humidity, with light / darkness = 16 / 8, for 2 days. After the culture, the mortality of the corn borers was evaluated (the larvae were determined to be dead if they could not crawl normally), and the test was performed in triplicate.

[0287]

[0288] wherein X represents the number of living insects before culture, and Y represents the number of living insects after culture.

[0289] The results of the insecticidal activity detection of the phenyl isoxazole derivative containing a triazole ring prepared in Examples 1-27 on corn borers are shown in Table 4.

[0290] Table 4 Results of insecticidal activity detection of the phenyl isoxazole derivative containing a triazole ring on corn borers

[0291]

[0292] As can be seen from the data in Table 4, the phenyl isoxazole derivative containing a triazole ring provided in the application has a death rate of 100% on the corn borer at a concentration of 50 μg / mL, which is equivalent to that of flucycloxuron, which shows that the phenyl isoxazole derivative containing a triazole ring provided in the application has certain insecticidal activity on the corn borer and can be applied to the prevention and control of agricultural pests as an active ingredient of a pesticide.

[0293] V. Insecticidal activity detection on aphids

[0294] The 3-5 cm broad bean seedlings were washed with clean water, transplanted into plastic culture dishes, and then added with an appropriate amount of quartz sand, and then 4 mL of water was added for moisturizing;

[0295] 30-50 aphids were selected from the broad bean seedlings, transferred to the broad bean seedlings with a soft hair pen, covered with a nylon filter screen, and then 50 μg / mL of the solution of the compound to be detected (the phenyl isoxazole derivative containing a triazole ring prepared in Examples 1-27) was sprayed with a small watering can, cultured in a culture box at 26°C and 70% relative humidity, light / darkness = 14 / 10, for 2 days, and then the mortality of aphids was evaluated (the larvae were determined to be dead if they could not normally crawl) after the culture was completed, and the detection was carried out in parallel for 3 times;

[0296]

[0297] Wherein, X is the number of live insects before culture, and Y is the number of live insects after culture;

[0298] The insecticidal activity detection results of the phenyl isoxazole derivative containing a triazole ring prepared in Examples 1-27 on aphids are shown in Table 5.

[0299] Table 5 Insecticidal activity detection results of the phenyl isoxazole derivative containing a triazole ring on aphids

[0300]

[0301] As can be seen from the data in Table 5, the phenyl isoxazole derivative containing a triazole ring provided in the application has a death rate of 100% on the corn borer at a concentration of 50 μg / mL, which is equivalent to that of flucycloxuron, which shows that the phenyl isoxazole derivative containing a triazole ring provided in the application has certain insecticidal activity on the corn borer and can be applied to the prevention and control of agricultural pests as an active ingredient of a pesticide.

[0302] VI. Toxicity test

[0303] The compound to be detected (the phenyl isoxazole derivative containing triazole ring prepared in Examples 1-27) was dissolved in dimethyl sulfoxide, and then diluted to 50 μg / mL with sugar water (1 g: 1 g); the obtained solution of the compound to be detected was added to a honey feeding trough, and 15 bees were added to a bee incubation box, after 5 h of feeding of the bees, the honey feeding trough was removed, the bee incubation box was cultured in an incubator at 26°C, 70% relative humidity, light / darkness = 14 / 10, for 2 days, after the culture, the mortality of the bees was evaluated (the larvae were gently touched, and the larvae that could not normally crawl were determined as dead), and the detection was performed in parallel for 3 times;

[0304]

[0305] Wherein, X is the number of living insects before culture, and Y is the number of living insects after culture;

[0306] The toxicity test results of the phenyl isoxazole derivative containing triazole ring prepared in Examples 1-27 are shown in Table 6.

[0307] Table 6 Toxicity test results of the phenyl isoxazole derivative containing triazole ring

[0308]

[0309] As shown by the data in Table 5, the phenyl isoxazole derivative containing triazole ring provided by the present application has a mortality rate of 0% on bees when the concentration is 50 μg / mL, while the mortality rate of fluoxastrobin on bees is 100%, which indicates that the phenyl isoxazole derivative containing triazole ring provided by the present application has low toxicity, and can be applied to the prevention and control of agricultural pests as a pesticide active ingredient.

[0310] Finally, it should be noted that: the above examples are only used to illustrate the technical solutions of the present application rather than limit them, although the present application has been described in detail with reference to the above examples, those skilled in the art should understand that: the specific embodiments of the present application can be modified or replaced by the same, without departing from the spirit and scope of the present application, any modification or equivalent replacement thereof should be covered in the protection scope of the claims of the present application.

Claims

1. A phenylisoxazole derivative containing a triazole ring, characterized in that, The structural formula of the phenylisoxazole derivative containing a triazole ring is: In the formula, R 1 R 2 R 3 It can be hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 haloalkoxy; R 4 It can be hydrogen, halogen, cyano, nitro, C1-C6 alkyl, or C1-C6 haloalkyl; R 5 It can be hydrogen, halogen, cyano, nitro, hydroxyl, amino, mercapto, C1-C6 alkoxy, C1-C6 alkenyl, or C1-C6 cycloalkyl. R 6 It is trifluoroacetyl, dichloroacetyl, trichloroacetyl, methylalkoxyoxalyl, benzoyl, 2-chloro-4-fluorobenzoyl, 3-chloro-3-chlorobenzoyl, 2-trifluoromethylbenzoyl, 3-trifluoromethylbenzoyl, 4-trifluoromethylbenzoyl, 2-fluorobenzoyl, 3-fluorobenzoyl, 4-fluorobenzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 2-methylbenzoyl, 3-methylbenzoyl, or 4-methylbenzoyl.

2. A method for preparing a triazole ring-containing phenylisoxazole derivative as described in claim 1, characterized in that, Includes the following steps: 1) Compound A, hydroxylamine hydrochloride, sodium carbonate, and an organic solvent are mixed and reacted to obtain compound B; The structural formula of compound A is as follows: The structural formula of compound B is 2) The compound B obtained in step 1) was subjected to chlorination. Then, the chlorinated product of compound B, compound C and organic solvent were mixed and reacted to obtain compound D. The structural formula of compound C is as follows: The structural formula of compound D is 3) Mix compound D and compound E obtained in step 2), base and organic solvent, and react to obtain compound F; The structural formula of compound E is as follows: The structural formula of compound F is 4) Combine compound F obtained in step 3) with R-containing compound F. 6 The reactants of the group are mixed with a base and reacted to obtain the phenylisoxazole derivative containing a triazole ring.

3. The preparation method according to claim 2, characterized in that, In step 1), the organic solvent is one or more of methanol, ethanol, triethylamine, dichloromethane, chloroform, ethyl acetate, acetonitrile, toluene, xylene, tetrahydrofuran, N,N-dimethylformamide, n-propanol, and water; the molar ratio of compound A, hydroxylamine hydrochloride, sodium carbonate, and the organic solvent is 1:(1-3):(1-5):(2-5).

4. The preparation method according to claim 2, characterized in that, In step 2), the reagent for the chlorination reaction is N-chlorosuccinimide; the organic solvent is one or more of methanol, ethanol, triethylamine, dichloromethane, chloroform, ethyl acetate, acetonitrile, toluene, xylene, tetrahydrofuran, N,N-dimethylformamide, n-propanol, and water; the molar ratio of compound B, the reagent for the chlorination reaction, compound C, and the organic solvent is 1:(1-4):(1-3):(2-8).

5. The preparation method according to claim 2, characterized in that, In step 3), the alkali is lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, potassium tert-butoxide, ammonia, methylamine, ethylamine, propylamine, dimethylamine, diethylamine, dipropylamine, trimethylamine, triethylamine, tripropylamine, N,N-diisopropylethylamine, sodium acetate, potassium acetate, or sodium bicarbonate; the organic solvent is one or more of methanol, ethanol, triethylamine, dichloromethane, chloroform, ethyl acetate, acetonitrile, toluene, xylene, tetrahydrofuran, N,N-dimethylformamide, n-propanol, and water; the molar ratio of compound D, compound E, alkali, and organic solvent is 1:(1-4):(1-3):(2-8).

6. The preparation method according to claim 2, characterized in that, In step 4), the alkali is lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, potassium tert-butoxide, ammonia, methylamine, ethylamine, propylamine, dimethylamine, diethylamine, dipropylamine, trimethylamine, triethylamine, tripropylamine, N,N-diisopropylethylamine, sodium acetate, potassium acetate, or sodium bicarbonate; the compound F, containing R... 6 The molar ratio of the reactant to the base is 1:(1-4):(1-3).

7. A phenylisoxazole derivative containing a triazole ring, characterized in that, The structures of the triazole ring-containing phenylisoxazole derivatives are selected from:

8. The application of a triazole ring-containing phenylisoxazole derivative as described in claim 1 or 7 as an active pesticide ingredient in the control of agricultural pests, wherein the agricultural pests are selected from diamondback moth, fall armyworm, cotton bollworm, corn borer, and aphid.

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