Phenylisoxazole derivative containing triazole ring as well as preparation method and application of phenylisoxazole derivative

Abstract

The invention relates to the technical field of pesticide chemistry, and discloses a triazole ring-containing phenylisoxazole derivative as well as a preparation method and application thereof. The structural formula of the phenyl isoxazole derivative containing the triazole ring is # imgabs0. When the concentration of the phenyl isoxazole derivative containing the triazole ring is 50 mu g / mL, the phenyl isoxazole derivative containing the triazole ring shows good insecticidal activity on agricultural pests such as plutella xylostella, spodoptera frugiperda, cotton bollworm, corn borer and aphid, and therefore the phenyl isoxazole derivative containing the triazole ring has good insecticidal activity on agricultural pests such as corn borer and aphid. The triazole ring-containing phenylisoxazole derivative provided by the invention can be used as a pesticide active component to be applied to prevention and control of agricultural pests.

Description

Technical Field

[0001] The present invention relates to the technical field of pesticide chemistry, and in particular, to a phenylisoxazole derivative containing a triazole ring, a preparation method thereof, and an application thereof. Background Art

[0002] With the development of green pesticides, isoxazole compounds have been widely used in a variety of insecticides. For example, isoxazole compounds are contained in isoxazole insecticides such as fluralaner, fluxametamide, isoxazolinon, pyraclonil, afoxolaner, etc. Isoxazole insecticides are favored by agricultural workers due to their high activity, low toxicity, long residual period, etc., and they have high insecticidal activity against various pests such as Lepidoptera, Hemiptera, Thysanoptera, Coleoptera, Diptera, and Acarina.

[0003] Triazole fungicides containing triazole heterocyclic derivatives have attracted much attention due to their broad activity against pathogenic bacteria in Ascomycotina, Basidiomycotina, and Deuteromycotina. Moreover, triazole heterocyclic derivatives also show certain plant growth regulatory activities, bringing more possibilities to agricultural production, which makes triazole fungicides occupy a prominent position in the fungicide market.

[0004] In view of the significant activities of isoxazole insecticides and triazole fungicides in insecticidal and fungicidal aspects, splicing and modifying isoxazole fragments and triazole heterocyclic fragments to synthesize a series of new pesticides with good insecticidal activity is expected to further promote the prevention and control of agricultural pests. Summary of the Invention

[0005] The purpose of the present invention is to provide a phenylisoxazole derivative containing a triazole ring, a preparation method thereof, and an application thereof. The phenylisoxazole derivative containing a triazole ring is used as a pesticide active ingredient in the prevention and control of agricultural pests, and shows good insecticidal activity against agricultural pests such as Plutella xylostella, Spodoptera frugiperda, Helicoverpa armigera, Ostrinia furnacalis, and aphids.

[0006] To achieve the above purpose, the present invention provides the following technical solutions:

[0007] One of the technical solutions of the present invention:

[0008] A phenylisoxazole derivative containing a triazole ring, and its structural formula is:

[0009]

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

[0011] R4 is hydrogen, halogen, cyano, nitro, C1-C6 alkyl or C1-C6 haloalkyl;

[0012] R 5 is hydrogen, halogen, cyano, nitro, hydroxy, amino, mercapto, C1-C6 alkoxy, C1-C6 alkenyl, C1-C6 cycloalkyl or aryl;

[0013] R 6 is hydrogen, C1-C6 alkoxy, C1-C6 alkenyl, C1-C6 alkoxyoxalyl, alkanoyl, C1-C6 cycloalkyl, haloalkanoyl, benzoyl, substituted benzoyl, phenyl, substituted phenyl, heteroaryl or substituted heteroaryl.

[0014] Preferably, in the formula, R 1 、R 2 、R 3 are hydrogen or chlorine; R 4 is trifluoromethyl; R 5 is cyano; R 6 is acetyl, cycloalkanoyl, methyl alkoxyoxalyl, benzoyl or substituted benzoyl.

[0015] More preferably, in the formula, R 1 、R 3 are chlorine; R 2 is hydrogen or chlorine; R 4 is trifluoromethyl; R 5 is cyano; R 6 is trifluoroacetyl, dichloroacetyl, trichloroacetyl, cycloalkanoyl, methyl alkoxyoxalyl, 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 invention include:

[0017]

[0018]

[0019] The second technical solution of the present invention:

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

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

[0022] Among them, the structural formula of compound A is The structural formula of compound B is

[0023] 2) Chlorinate the compound B obtained in step 1), and then mix the chlorinated product of compound B, compound C and an organic solvent, and react to obtain compound D;

[0024] Among them, the structural formula of compound C is The structural formula of compound D is

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

[0026] Among them, the structural formula of compound E is The structural formula of compound F is

[0027]

[0028] 4) Mix the compound F, R 6 and a base, and react to obtain the phenylisoxazole derivative containing a triazole ring.

[0029] Furthermore, 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] Furthermore, in step 1), the molar ratio of compound A, hydroxylamine hydrochloride, sodium carbonate and the organic solvent is 1∶(1~3)∶(1~5)∶(2~5).

[0031] Furthermore, in step 2), the chlorinating agent is N-chlorosuccinimide.

[0032] Furthermore, 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] Furthermore, in step 2), the molar ratio of compound B, the chlorinating agent, 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, ammonia water, 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 compound D, compound E, the base and the organic solvent is 1∶(1 - 4)∶(1 - 3)∶(2 - 8).

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

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

[0039] Even further, the reducing agent is one of Na, K, Mg, Al, Zn, Fe, Cu, LiAlH4, NaBH4, H2S, Na2SO3, H2C2O4, Na2S2O4 and N2H4; the molar ratio of compound D, the reducing agent, 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, ammonia water, 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 compound F, R 6 and the base is 1∶(1 - 4)∶(1 - 3).

[0042] The synthesis route of the preparation method of the phenylisoxazole derivative containing a triazole ring according to the present invention is shown as follows:

[0043]

[0044] The third technical solution of the present invention:

[0045] The application of the above-mentioned phenylisoxazole derivatives containing a triazole ring as pesticidal active ingredients in the control of agricultural pests.

[0046] Furthermore, the agricultural pests include Plutella xylostella, Spodoptera frugiperda, Helicoverpa armigera, Ostrinia furnacalis and aphids.

[0047] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0048] When the concentration of the phenylisoxazole derivative containing a triazole ring provided by the present invention is 50 μg / mL, it shows good insecticidal activity against agricultural pests such as Plutella xylostella, Spodoptera frugiperda, Helicoverpa armigera, Ostrinia furnacalis and aphids. Therefore, the phenylisoxazole derivative containing a triazole ring provided by the present invention can be used as a pesticidal active ingredient in the control of agricultural pests. Detailed Description of the Invention

[0049] The various exemplary embodiments of the present invention will now be described in detail. This detailed description should not be construed as a limitation of the present invention, but rather as a more detailed description of certain aspects, features and embodiments of the present invention. It should be understood that the terms used in the present invention are only for describing particular embodiments and are not intended to limit the present invention.

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

[0051] Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by those of ordinary skill in the art to which the present invention pertains. Although the present invention only describes preferred methods and materials, any methods and materials similar or equivalent to those described herein can also be used in the implementation or testing of the present invention. All documents mentioned in this specification are incorporated by reference to disclose and describe the methods and / or materials related to the documents. In case of conflict with any incorporated document, the content of this specification shall prevail.

[0052] Without departing from the scope or spirit of the present invention, various improvements and changes can be made to the specific embodiments of the present invention specification, which are obvious to those skilled in the art. Other embodiments obtained from the specification of the present invention are obvious to those skilled in the art. The specification and examples of the present invention are only exemplary.

[0053] Regarding the terms "comprising", "including", "having", "containing", etc. used herein, they are all open-ended terms, meaning including but not limited to.

[0054] Example 1

[0055] A phenylisoxazole derivative containing a triazole ring

[0056] 1) Add 3-cyano-4-fluorobenzaldehyde (Compound A, 20.0 g, 0.13 mol), hydroxylamine hydrochloride (14 g, 0.2 mol) and a methanol-aqueous solution (250 mL, 1 mol∶2 mol) to a 250 mL round-bottom flask, stir and react at room temperature for 2 h, then slowly add sodium carbonate (25 g, 0.23 mol), further stir and react at room temperature for 2 h. After the reaction is completed, add ice cubes to precipitate a solid, filter by suction, dry, and purify by column chromatography to obtain a yellow-green solid (E)-2-fluoro-5-(hydroxyimino)methylbenzonitrile (Compound B);

[0057]

[0058] After detection, the yield of Compound B is 82%;

[0059] 2) Add (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) to a 250 mL round-bottom flask, stir and react at room temperature for 30 min, then add 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), stir and react at room temperature for 18 h. After the reaction is completed, wash with water, extract with dichloromethane, dry over anhydrous sodium sulfate, concentrate under vacuum, and purify 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] After detection, the yield of Compound D is 95.7%;

[0062] 3) 3-Amino-1,2,4-triazole (Compound E, 1.7 g, 20 mmol), potassium tert-butoxide (2.8 g, 25 mmol), and DMF (50 mL) were added to a 100 mL round-bottom flask, and the mixture was 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. The mixture was stirred and refluxed at 100 °C for 4 h. After the reaction was completed, it was concentrated under vacuum and purified by column chromatography to obtain a pale yellow solid, 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl nitrile (Compound F);

[0063]

[0064] The yield of Compound F was detected to be 44%;

[0065] 4) 2-(5-Amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl nitrile (Compound F, 0.3 g, 0.64 mmol), 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, and the mixture was stirred and refluxed at 120 °C for 4 h. After the reaction was completed, it was concentrated under vacuum and purified by column chromatography to obtain a pale yellow solid, 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, namely the triazole ring-containing phenyl isoxazole derivative;

[0066]

[0067] The yield of the triazole ring-containing phenyl isoxazole derivative was detected to be 16%.

[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 phenylisoxazole derivative containing a triazole ring

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

[0072] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl nitrile (Compound F, 0.3 g, 0.64 mmol), trifluoroacetyl chloride (0.12 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a light brown solid 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, which is the phenylisoxazole derivative containing a triazole ring;

[0073]

[0074] Upon detection, the yield of the phenylisoxazole derivative containing a triazole ring is 13.3%.

[0075] 1 HNMR(600MHz,)δ8.35(s,1H),8.08(s,1H),7.47(d,J=1.4Hz,1H),7.45(dd,J=6.9,1.4Hz,1H),7.43(d,J=6.9Hz,1H),7.00(s,2H),6.96–6.95(m,1H),4.28(d,J=13.7Hz,1H),3.99(d,J=13.7Hz,1H).

[0076] Example 3

[0077] A phenylisoxazole derivative containing a triazole ring

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

[0079] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a brown solid 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-dichloroacetamide, namely the phenyl isoxazole derivative containing a triazole ring;

[0080]

[0081] It was detected that the yield of the phenyl isoxazole derivative containing a triazole ring was 12.5%.

[0082] 1 H NMR (500 MHz,) 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 phenyl isoxazole derivative containing a triazole ring

[0085] Steps 1) to 3) are the same as in Example 1;

[0086] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain the white solid 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-trichloroacetamide, namely the phenyl isoxazole derivative containing a triazole ring;

[0087]

[0088] It was detected that the yield of the phenyl isoxazole derivative containing a triazole ring was 41.7%.

[0089] 1 HNMR(500MHz,)δ8.55(s,1H),8.29(s,1H),7.67(s,1H),7.66–7.61(m,2H),7.20(s,2H),7.16(d,J=1.3Hz,1H),4.49(d,J=13.8Hz,1H),4.19(d,J=13.8Hz,1H).

[0090] Example 5

[0091] A phenyl isoxazole derivative containing a triazole ring

[0092] Steps 1) to 3) are the same as in Example 1;

[0093] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid N-(1-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)benzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0094]

[0095] After detection, the yield of the phenylisoxazole derivative containing a triazole ring is 50%.

[0096] 1 HNMR(500MHz,)δ9.40(s,1H),8.04(s,1H),7.64(s,1H),7.55(dd,J=10.5,4.7Hz,4H),7.24(t,J=5.9Hz,1H),7.20–7.17(m,4H),7.12(t,J=1.5Hz,1H),4.49(d,J=13.8Hz,1H),4.22(d,J=13.9Hz,1H).

[0097] Example 6

[0098] A phenylisoxazole derivative containing a triazole ring

[0099] Steps 1) to 3) are the same as in Example 1;

[0100] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid 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-chloro-4-fluorobenzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0101]

[0102] It was detected that the yield of the phenylisoxazole derivative containing a triazole ring was 50%.

[0103] 1 HNMR(500MHz,)δ9.76(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=0.7Hz,1H),6.97–6.92(m,1H),6.88(dd,J=9.2,3.8Hz,1H),4.49(d,J=13.9Hz,1H),4.24(d,J=13.9Hz,1H).

[0104] Example 7

[0105] A phenylisoxazole derivative containing a triazole ring

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

[0107] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid N-(1-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-3,5-dichlorobenzamide, namely the phenyl isoxazole derivative containing a triazole ring;

[0108]

[0109] It was detected that the yield of the phenyl isoxazole derivative containing a triazole ring was 33.3%.

[0110] 1 HNMR(600MHz,)δ9.08(s,1H),8.80(s,1H),8.10–8.08(m,1H),8.07–8.03(m,2H),7.83(d,J=1.9Hz,2H),7.58(t,J=1.8Hz,1H),7.51(d,J=1.6Hz,2H),7.46(dd,J=2.4,1.2Hz,1H),4.12(d,J=17.1Hz,1H),3.75(d,J=17.2Hz,1H).

[0111] Example 8

[0112] A phenyl isoxazole derivative containing a triazole ring

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

[0114] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (Compound F, 0.3 g, 0.64 mmol), 2-(trifluoromethyl)benzoyl chloride (0.13 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid 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-(trifluoromethyl)benzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0115]

[0116] It was detected that the yield of the phenylisoxazole derivative containing a triazole ring was 26.7%.

[0117] 1 HNMR(500MHz,)δ9.83(s,1H),7.67(s,1H),7.58(t,J=18.9Hz,3H),7.43(d,J=6.1Hz,1H),7.40–7.30(m,3H),7.18(s,2H),7.13(s,1H),4.49(d,J=13.8Hz,1H),4.22(d,J=13.8Hz,1H).

[0118] Example 9

[0119] A phenylisoxazole derivative containing a triazole ring

[0120] Steps 1) to 3) are the same as in Example 1;

[0121] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl nitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid N-(1-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-3-trifluoromethylbenzamide, namely the phenyl isoxazole derivative containing a triazole ring;

[0122]

[0123] It was detected that the yield of the phenyl isoxazole derivative containing a triazole ring was 76.7%.

[0124] 1 HNMR(600MHz,)δ9.50(s,1H),8.84(s,1H),8.29(s,1H),8.21(d,J=7.8Hz,1H),8.11–8.08(m,2H),8.06(dd,J=8.7,1.9Hz,1H),7.87(d,J=7.8Hz,1H),7.69(t,J=7.8Hz,1H),7.51(d,J=1.6Hz,2H),7.46(t,J=1.8Hz,1H),4.12(d,J=17.1Hz,1H),3.75(d,J=17.2Hz,1H).

[0125] Example 10

[0126] A phenyl isoxazole derivative containing a triazole ring

[0127] Steps 1) to 3) are the same as in Example 1;

[0128] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain the white solid N-(1-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-4-trifluoromethylbenzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0129]

[0130] The yield of the phenylisoxazole derivative containing a triazole ring was detected 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 phenylisoxazole derivative containing a triazole ring

[0134] Steps 1) to 3) are the same as in Example 1;

[0135] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid 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-fluorobenzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0136]

[0137] The yield of the phenylisoxazole derivative containing a triazole ring was detected to be 72.5%.

[0138] 1 HNMR(400MHz,CDCl3)δ9.31(s,2H),9.31(s,1H),8.87(s,2H),8.87(s,2H),8.22(t,J=7.4Hz,2H),8.11(d,J=8.9Hz,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=7.5Hz,2H),7.27(s,2H),4.13(d,J=17.2Hz,2H),4.13(d,J=17.2Hz,2H),3.76(d,J=17.3Hz,2H),3.76(d,J=17.3Hz,2H).

[0139] Example 12

[0140] A phenylisoxazole derivative containing a triazole ring

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

[0142] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid N-(1-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-3-fluorobenzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0143]

[0144] The yield of the phenylisoxazole derivative containing a triazole ring was detected to be 33.3%.

[0145] 1 HNMR(400MHz,CDCl3)δ10.44(s,1H),8.90(s,1H),8.11(d,J=7.8Hz,2H),8.04(d,J=8.6Hz,1H),7.89(t,J=8.8Hz,2H),7.80(dd,J=18.3,9.2Hz,2H),7.52(d,J=5.4Hz,2H),7.45(s,1H),4.13(d,J=17.3Hz,1H),3.77(d,J=17.3Hz,1H).

[0146] Example 13

[0147] A phenylisoxazole derivative containing a triazole ring

[0148] Steps 1) to 3) are the same as in Example 1;

[0149] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid N-(1-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-4-fluorobenzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0150]

[0151] The yield of the phenylisoxazole derivative containing a triazole ring was detected to be 45.5%.

[0152] 1 HNMR(400MHz,CDCl3)δ10.46(s,1H),8.91(s,1H),8.13(d,J=8.4Hz,3H),8.05(d,J=9.6Hz,1H),7.51(s,1H),7.47–7.43(m,1H),7.21(t,J=8.5Hz,1H),7.18–7.08(m,3H),4.13(d,J=17.3Hz,1H),3.77(d,J=17.2Hz,1H).

[0153] Example 14

[0154] A phenylisoxazole derivative containing a triazole ring

[0155] Steps 1) to 3) are the same as in Example 1;

[0156] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid 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-chlorobenzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0157]

[0158] The yield of the phenylisoxazole derivative containing a triazole ring was detected to be 62%.

[0159] 1 HNMR(600MHz,)δ9.31(s,1H),7.64(s,1H),7.46(s,1H),7.40(dd,J=6.9,1.3Hz,1H),7.17(d,J=5.8Hz,1H),6.99(s,2H),6.98–6.95(m,2H),6.93(ddd,J=6.8,4.4,1.3Hz,2H),4.29(d,J=13.8Hz,1H),4.01(d,J=13.8Hz,1H).

[0160] Example 15

[0161] A phenylisoxazole derivative containing a triazole ring

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

[0163] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid N-(1-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-3-chlorobenzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0164]

[0165] The yield of the phenylisoxazole derivative containing a triazole ring was detected to be 47.5%.

[0166] 1 HNMR(600MHz,)δ9.90(s,1H),8.57(s,1H),7.95(t,J=1.2Hz,1H),7.93(d,J=1.7Hz,1H),7.92(d,J=2.6Hz,1H),7.87(dd,J=7.0,1.5Hz,1H),7.84(t,J=6.9Hz,2H),7.51–7.50(m,1H),7.45(t,J=4.9Hz,2H),7.43–7.41(m,1H),7.39(t,J=6.3Hz,1H),4.75(d,J=13.7Hz,1H),4.46(d,J=13.7Hz,1H).

[0167] Example 16

[0168] A phenylisoxazole derivative containing a triazole ring

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

[0170] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl nitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid N-(1-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-4-chlorobenzamide, namely the phenyl isoxazole derivative containing a triazole ring;

[0171]

[0172] The yield of the phenyl isoxazole derivative containing a triazole ring was detected to be 52%.

[0173] 1 H NMR (500 MHz,) 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 phenyl isoxazole derivative containing a triazole ring

[0176] Steps 1) to 3) are the same as in Example 1;

[0177] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid 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-methylbenzamide, namely the triazole ring-containing phenyl isoxazole derivative;

[0178]

[0179] After detection, the yield of the triazole ring-containing phenyl isoxazole derivative is 42%.

[0180] 1 HNMR(600MHz,)δ9.19(s,1H),8.28(s,1H),7.94(d,J=6.9Hz,1H),7.92(d,J=1.4Hz,1H),7.88(dd,J=6.9,1.6Hz,2H),7.54(d,J=5.9Hz,1H),7.46(s,2H),7.42(dd,J=3.2,1.8Hz,1H),7.41–7.37(m,2H),4.75(s,J=13.7Hz,1H),4.45(d,J=13.7Hz,1H),3.50(s,3H).

[0181] Example 18

[0182] A triazole ring-containing phenyl isoxazole derivative

[0183] Steps 1) to 3) are the same as in Example 1;

[0184] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid N-(1-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-3-methylbenzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0185]

[0186] The yield of the phenylisoxazole derivative containing a triazole ring was detected to be 58.6%.

[0187] 1 HNMR(600MHz,)δ8.65(s,1H),8.04(s,1H),7.47(dd,J=6.3,4.2Hz,2H),7.41(dd,J=6.9,1.3Hz,2H),7.25(s,1H),7.22(dd,J=4.5,2.3Hz,1H),6.99(d,J=0.8Hz,2H),6.95(t,J=1.3Hz,1H),6.91(d,J=3.9Hz,2H),4.28(d,J=13.7Hz,1H),4.00(d,J=13.7Hz,1H),2.95(s,3H).

[0188] Example 19

[0189] A phenylisoxazole derivative containing a triazole ring

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

[0191] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid N-(1-(2-cyano-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-1H-1,2,4-triazol-5-yl)-4-methylbenzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0192]

[0193] After detection, the yield of the phenylisoxazole derivative containing a triazole ring is 21.6%.

[0194] 1 HNMR(600MHz,)δ8.84(s,1H),8.09(s,1H),7.50(d,J=7.0Hz,1H),7.47(d,J=1.5Hz,1H),7.41(dd,J=6.7,1.5Hz,1H),7.39(d,J=6.5Hz,2H),7.35(d,J=6.4Hz,2H),7.00(d,J=0.8Hz,2H),6.95(t,J=1.3Hz,1H),4.28(d,J=13.7Hz,1H),3.99(d,J=13.7Hz,1H),2.94(s,3H).

[0195] Example 20

[0196] A phenylisoxazole derivative containing a triazole ring

[0197] Step 1) is the same as in Example 1;

[0198] 2) Add (E)-2-fluoro-5-(hydroxyimino)methylbenzonitrile (Compound B, 16.4 g, 0.11 mol) obtained in step 1) and NCS (30 g, 0.22 mol) into a 250 mL round-bottom flask, stir and react at room temperature for 30 min. Then add 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), stir and react at room temperature for 18 h. After the reaction is completed, wash with water, extract with dichloromethane, dry with anhydrous sodium sulfate, concentrate under vacuum, and purify by column chromatography to obtain white solid 5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-fluorobenzonitrile (Compound D);

[0199]

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

[0201] 3) Add 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) into a 100 mL round-bottom flask, stir and react at room temperature for 1 h. Then slowly add 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), stir and reflux at 100 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain light yellow solid 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylbenzonitrile (Compound F);

[0202]

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

[0204] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain the white solid 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-fluorobenzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0205]

[0206] After detection, the yield of the phenylisoxazole derivative containing a triazole ring is 42%.

[0207] 1 HNMR(600MHz,)δ9.33(d,J=13.8Hz,1H),8.83(s,1H),8.16(td,J=7.8,1.7Hz,1H),8.09–8.08(m,1H),8.07–8.02(m,2H),7.64(s,2H),7.59–7.54(m,1H),7.35–7.30(m,1H),7.21(dd,J=11.8,8.5Hz,1H),4.13(d,J=17.2Hz,1H),3.78(d,J=17.2Hz,1H).

[0208] Example 21

[0209] A phenylisoxazole derivative containing a triazole ring

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

[0211] 4) Add 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), 3-fluorobenzoyl chloride (0.09 g, 0.64 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain the white solid 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-fluorobenzamide, namely the phenyl isoxazole derivative containing a triazole ring;

[0212]

[0213] After detection, the yield of the phenyl isoxazole derivative containing a triazole ring is 42%.

[0214] 1 HNMR(600MHz,)δ9.10(s,1H),8.00(s,1H),7.46(d,J=1.2Hz,1H),7.43–7.39(m,2H),7.23(d,J=6.2Hz,1H),7.18–7.16(m,1H),7.10(s,2H),6.99(td,J=6.4,4.5Hz,1H),6.82(td,J=6.7,1.8Hz,1H),4.29(d,J=13.8Hz,1H),4.01(d,J=13.8Hz,1H).

[0215] Example 22

[0216] A phenyl isoxazole derivative containing a triazole ring

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

[0218] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain the white solid 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-fluorobenzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0219]

[0220] The yield of the phenylisoxazole derivative containing a triazole ring was detected 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 phenylisoxazole derivative containing a triazole ring

[0224] Steps 1) - 2) are the 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, and the mixture was 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. The mixture was stirred and refluxed at 100 °C for 4 h. Finally, Fe powder (11 g, 20 mmol) was added, and the mixture was stirred and refluxed at 100 °C for 2 h. After the reaction was completed, it was concentrated under vacuum and purified by column chromatography to obtain a pale yellow solid 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (Compound F);

[0226]

[0227] The yield of Compound F was detected to be 61%;

[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)phenylcarbonitrile (Compound F, 0.3 g, 0.64 mmol), 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, and the mixture was stirred and refluxed at 120 °C for 4 h. After the reaction was completed, it was concentrated under vacuum and purified by column chromatography to obtain a white solid 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, namely the triazole ring-containing phenylisoxazole derivative;

[0229]

[0230] The yield of the triazole ring-containing phenylisoxazole derivative was detected to be 57%.

[0231] 1HNMR(500MHz,)δ10.10(s,1H),8.32(s,1H),7.65(d,J=1.4Hz,1H),7.57(dd,J=6.9,1.4Hz,1H),7.25(d,J=15.2Hz,3H),7.21–7.18(m,1H),7.01–6.99(m,2H),6.96–6.94(m,1H),4.60(d,J=14.7Hz,1H),4.52(d,J=14.8Hz,1H).

[0232] Example 24

[0233] A phenylisoxazole derivative containing a triazole ring

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

[0235] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) to a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain the white solid 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-chlorobenzamide, namely the phenylisoxazole derivative containing a triazole ring;

[0236]

[0237] The yield of the phenylisoxazole derivative containing a triazole ring was detected to be 34.6%.

[0238] 1 HNMR(500MHz,)δ10.06(s,1H),8.38(s,1H),7.68(d,J=1.5Hz,1H),7.60(dd,J=6.9,1.7Hz,1H),7.43(t,J=4.3Hz,2H),7.38–7.35(m,1H),7.26(s,2H),7.16–7.13(m,1H),7.05(t,J=6.3Hz,1H),4.62(d,J=14.7Hz,1H),4.55(d,J=14.8Hz,1H).

[0239] Example 25

[0240] A phenylisoxazole derivative containing a triazole ring

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

[0242] 4) Add 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), 4-chlorobenzoyl chloride (0.093 g, 0.6 mmol), triethylamine (0.1 g, 0.96 mmol) and dichloroethane (20 mL) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain the white solid 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, namely the phenylisoxazole derivative containing a triazole ring;

[0243]

[0244] After detection, the yield of the phenylisoxazole derivative containing a triazole ring is 52%.

[0245] 1 HNMR(500MHz,)δ10.00(s,1H),8.36(s,1H),7.65(d,J=1.6Hz,1H),7.57(dd,J=6.9,1.6Hz,1H),7.42–7.38(m,3H),7.24(s,2H),7.07–7.04(m,2H),4.60(d,J=14.7Hz,1H),4.52(d,J=14.8Hz).

[0246] Example 26

[0247] A phenylisoxazole derivative containing a triazole ring

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

[0249] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid 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-methylbenzamide, namely the triazole ring-containing phenylisoxazole derivative;

[0250]

[0251] The yield of the triazole ring-containing phenylisoxazole derivative was detected to be 44.8%.

[0252] 1 H NMR (400 MHz, CDCl3) 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 triazole ring-containing phenylisoxazole derivative

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

[0256] 4) Add 2-(5-amino-1H-1,2,4-triazol-1-yl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenylcarbonitrile (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) into a 50 mL round-bottom flask, stir and reflux at 120 °C for 4 h. After the reaction is completed, concentrate under vacuum and purify by column chromatography to obtain a pale yellow solid 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, namely the triazole ring-containing phenylisoxazole derivative;

[0257]

[0258] The yield of the triazole ring-containing phenylisoxazole derivative was detected to be 51.5%.

[0259] 1 H NMR (400 MHz, CDCl3) 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. Detection of insecticidal activity against Plutella xylostella

[0262] Immerse fresh cabbages in the solution of the compound to be detected with a concentration of 50 μg / mL (the triazole ring-containing phenylisoxazole derivatives prepared in Examples 1-27), air dry after 30 seconds, and place them in a petri dish lined with filter paper. Then transfer 15 third-instar Plutella xylostella larvae into the petri dish, and culture them in an incubator at 26 °C and 85% relative humidity with a light / dark ratio of 16 / 8 for 2 days. After the culture is completed, evaluate the mortality rate of Plutella xylostella (gently touch the larvae, and if the larvae cannot crawl normally, it is considered dead), and detect in parallel 3 times;

[0263]

[0264] Among them, X - the number of live insects before culture, Y - the number of live insects after culture;

[0265] The detection results of the insecticidal activities of the phenylisoxazole derivatives containing a triazole ring prepared in Examples 1 to 27 against Plutella xylostella are shown in Table 1;

[0266] Table 1 Detection results of the insecticidal activities of the phenylisoxazole derivatives containing a triazole ring against Plutella xylostella

[0267]

[0268] As can be seen from the data in Table 1, for a class of phenylisoxazole derivatives containing a triazole ring provided by the present invention, when the concentration is 50 μg / mL, the mortality rate against Plutella xylostella can reach 100%, which is comparable to that of fluxametamide. This indicates that the phenylisoxazole derivatives containing a triazole ring provided by the present invention have certain insecticidal activities against Plutella xylostella and can be used as pesticide active ingredients for the control of agricultural pests.

[0269] II. Detection of insecticidal activities against Spodoptera frugiperda

[0270] The solution of the compound to be detected with a concentration of 50 μg / mL (phenylisoxazole derivatives containing a triazole ring prepared in Examples 1 to 27) was added to a 24-well plate, and 24 third-instar Spodoptera frugiperda larvae were added to each well. The plate was placed in an incubator at 26 °C and 85% relative humidity with a light / dark cycle of 16 / 8 for 2 days. After the incubation, the mortality rate of Spodoptera frugiperda was evaluated (if the larvae could not crawl normally when gently touched, they were considered dead), and the detection was performed in parallel 3 times;

[0271]

[0272] Among them, X is the number of live insects before cultivation, and Y is the number of live insects after cultivation;

[0273] The detection results of the insecticidal activities of the phenylisoxazole derivatives containing a triazole ring prepared in Examples 1 to 27 against Spodoptera frugiperda are shown in Table 2;

[0274] Table 2 Detection results of the insecticidal activities of the phenylisoxazole derivatives containing a triazole ring against Spodoptera frugiperda

[0275]

[0276] As can be seen from the data in Table 2, for a class of phenylisoxazole derivatives containing a triazole ring provided by the present invention, when the concentration is 50 μg / mL, the mortality rate against Spodoptera frugiperda can reach 100%, which is comparable to that of fluxametamide. This indicates that the phenylisoxazole derivatives containing a triazole ring provided by the present invention have certain insecticidal activities against Spodoptera frugiperda and can be used as pesticide active ingredients for the control of agricultural pests.

[0277] III. Detection of insecticidal activities against Helicoverpa armigera

[0278] Add the solution of the compound to be detected with a concentration of 50 μg / mL (phenylisoxazole derivatives containing a triazole ring prepared in Examples 1-27) into a 24-well plate, and add 24 third-instar cotton bollworms to each well. Incubate in an incubator at 26 °C and 85% relative humidity with a light / dark cycle of 16 / 8 for 2 days. After the incubation, evaluate the mortality rate of the cotton bollworms (if the larvae cannot crawl normally when gently touched, it is considered dead), and perform parallel detections 3 times;

[0279]

[0280] Among them, X is the number of live insects before cultivation, and Y is the number of live insects after cultivation;

[0281] The detection results of the insecticidal activity of the phenylisoxazole derivatives containing a triazole ring prepared in Examples 1-27 against cotton bollworms are shown in Table 3;

[0282] Table 3 Detection results of the insecticidal activity of phenylisoxazole derivatives containing a triazole ring against cotton bollworms

[0283]

[0284] As can be seen from the data in Table 3, when the concentration of a class of phenylisoxazole derivatives containing a triazole ring provided by the present invention is 50 μg / mL, the mortality rate against cotton bollworms can reach 100%, which is comparable to that of flucoxadiazole. This indicates that the phenylisoxazole derivatives containing a triazole ring provided by the present invention have certain insecticidal activity against cotton bollworms and can be used as pesticide active ingredients in the control of agricultural pests.

[0285] IV. Detection of insecticidal activity against Ostrinia furnacalis

[0286] Add the solution of the compound to be detected with a concentration of 50 μg / mL (phenylisoxazole derivatives containing a triazole ring prepared in Examples 1-27) into a 24-well plate, and add 24 third-instar Ostrinia furnacalis to each well. Incubate in an incubator at 26 °C and 85% relative humidity with a light / dark cycle of 16 / 8 for 2 days. After the incubation, evaluate the mortality rate of the Ostrinia furnacalis (if the larvae cannot crawl normally when gently touched, it is considered dead), and perform parallel detections 3 times;

[0287]

[0288] Among them, X is the number of live insects before cultivation, and Y is the number of live insects after cultivation;

[0289] The detection results of the insecticidal activity of the phenylisoxazole derivatives containing a triazole ring prepared in Examples 1-27 against Ostrinia furnacalis are shown in Table 4;

[0290] Table 4 Detection results of the insecticidal activity of phenylisoxazole derivatives containing a triazole ring against Ostrinia furnacalis

[0291]

[0292] As can be seen from the data in Table 4, when the concentration of a class of phenylisoxazole derivatives containing a triazole ring provided by the present invention is 50 μg / mL, the mortality rate against Ostrinia furnacalis can reach 100%, which is comparable to that of fluxametamide. This indicates that the phenylisoxazole derivatives containing a triazole ring provided by the present invention have certain insecticidal activity against Ostrinia furnacalis and can be used as pesticide active ingredients for the control of agricultural pests.

[0293] V. Detection of Insecticidal Activity against Aphids

[0294] Wash the 3 - 5 cm broad bean seedlings with clean water and transplant them into a plastic petri dish, add an appropriate amount of quartz sand, and then drip 4 mL of water to keep it moist.

[0295] Select 30 - 50 aphids from the broad bean seedlings, transfer them to the broad bean seedlings with a soft brush, cover with a nylon filter net. After all the aphids climb onto the broad bean seedlings, spray the solution of the compound to be detected (phenylisoxazole derivatives containing a triazole ring prepared in Examples 1 - 27) with a concentration of 50 μg / mL using a small sprayer. Incubate in an incubator at 26°C and 70% relative humidity with a light / dark cycle of 14 / 10 for 2 days. After the incubation, evaluate the mortality rate of aphids (gently touch the larvae, and if the larvae cannot crawl normally, it is considered dead), and conduct parallel detections 3 times.

[0296]

[0297] Among them, X is the number of live insects before cultivation, and Y is the number of live insects after cultivation.

[0298] The detection results of the insecticidal activity of the phenylisoxazole derivatives containing a triazole ring prepared in Examples 1 - 27 against aphids are shown in Table 5.

[0299] Table 5 Detection Results of Insecticidal Activity of Phenylisoxazole Derivatives Containing a Triazole Ring against Aphids

[0300]

[0301] As can be seen from the data in Table 5, when the concentration of a class of phenylisoxazole derivatives containing a triazole ring provided by the present invention is 50 μg / mL, the mortality rate against aphids can reach 100%, which is comparable to that of fluxametamide. This indicates that the phenylisoxazole derivatives containing a triazole ring provided by the present invention have certain insecticidal activity against aphids and can be used as pesticide active ingredients for the control of agricultural pests.

[0302] VI. Toxicity Test

[0303] Dissolve the compound to be detected (the phenylisoxazole derivatives containing a triazole ring prepared in Examples 1 to 27) in dimethyl sulfoxide, and then dilute it to 50 μg / mL with sugar water (1 g∶1 g); add the resulting compound solution to be detected into the bee feeding trough, and add 15 bees to the bee culture box. After waiting for the bees to feed for 5 h, take out the bee feeding trough, and place the bee culture box in an incubator at 26 °C and 70% relative humidity with a light / dark cycle of 14 / 10 for 2 days. After the culture is completed, evaluate the bee mortality rate (if the larvae cannot crawl normally when gently touched, it is considered dead), and perform parallel detection 3 times;

[0304]

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

[0306] The toxicity test results of the phenylisoxazole derivatives containing a triazole ring prepared in Examples 1 to 27 are shown in Table 6;

[0307] Table 6 Toxicity test results of phenylisoxazole derivatives containing a triazole ring

[0308]

[0309] As can be seen from the data in Table 5, when the concentration of a class of phenylisoxazole derivatives containing a triazole ring provided by the present invention is 50 μg / mL, the lethality rate to bees is 0%, while the lethality rate of fluxametamide to bees is 100%. This indicates that the phenylisoxazole derivatives containing a triazole ring provided by the present invention have low toxicity and can be used as pesticide active ingredients for the control of agricultural pests.

[0310] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not intended to limit them. Although the present invention has been described in detail with reference to the above embodiments, those of ordinary skill in the art should understand that: modifications or equivalent substitutions can still be made to the specific embodiments of the present invention, and any modification or equivalent substitution without departing from the spirit and scope of the present invention should be covered by the protection scope of the claims of the present invention.

Claims

1. A phenylisoxazole derivative containing a triazole ring, characterized in that: The structural formula of the triazole ring-containing phenylisoxazole derivative is: In the formula, R 1 , R 2 , R 3 is hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 haloalkoxy; R 4 is hydrogen, halogen, cyano, nitro, C1-C6 alkyl or C1-C6 haloalkyl; R 5 is hydrogen, halogen, cyano, nitro, hydroxyl, amino, mercapto, C1-C6 alkoxy, C1-C6 alkenyl, C1-C6 cycloalkyl or aryl; R 6 It is hydrogen, C1-C6 alkoxy, C1-C6 alkenyl, C1-C6 alkoxyoxalyl, alkanoyl, C1-C6 cycloalkyl, halogenated alkanoyl, benzoyl, substituted benzoyl, phenyl, substituted phenyl, heterocyclic aromatic group or substituted heterocyclic aromatic group.

2. A method for preparing a triazole ring-containing phenylisoxazole derivative according to claim 1, characterized in that: The following steps are involved: 1) Compound A, hydroxylamine hydrochloride, sodium carbonate and an organic solvent are mixed and reacted to obtain compound B; Wherein, the structural formula of compound A is The structural formula of compound B is 2) Chlorinating the compound B obtained in step 1), and then mixing the chlorinated product of compound B, compound C and an organic solvent, and reacting them to obtain compound D; Among them, the structural formula of compound C is The structural formula of compound D is 3) mixing the compound D obtained in step 2), the compound E, a base and an organic solvent, and reacting them to obtain a compound F; Among them, the structural formula of compound E is The structural formula of compound F is 4) Compounds F and R obtained in step 3) 6 and a base to react to obtain the triazole ring-containing phenylisoxazole derivative.

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 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 chlorination agent 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, chlorination agent, compound C and 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 base is lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, potassium tert-butoxide, ammonia water, 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, base 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 base 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 compounds F, R 6 The molar ratio of the organic solvent to the base is 1:(1-4):(1-3).

7. Use of the triazole ring-containing phenylisoxazole derivative as claimed in claim 1 as an active ingredient of pesticide in agricultural pest control.

8. The use according to claim 7, characterized in that: The agricultural pests include diamondback moth, fall armyworm, cotton bollworm, corn borer and aphids.

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