Trifluoromethylpyridine derivative as well as preparation method and application thereof

Abstract

The invention provides a trifluoromethylpyridine derivative as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The trifluoromethyl alpha, beta-unsaturated imine is used for constructing the trifluoromethyl pyridine derivative, the trifluoromethyl pyridine derivative emits blue fluorescence when the wavelength is 300-500 nm, and the trifluoromethyl pyridine derivative has good optical properties and good antibacterial activity, is expected to be used in the fields of organic light-emitting materials and pesticides, and has good application prospects. The application prospect is wide; the preparation method is simple, convenient and rapid, the substrate range is wide, the used raw materials are cheap and easy to obtain, and environmental pollution is not caused; the preparation method of the trifluoromethylpyridine derivative has the advantages of simple process, high yield, good universality and the like, and has good practicability.

Description

Technical Field

[0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a trifluoromethylpyridine derivative and a preparation method and application thereof. Background Art

[0002] Pyridine is an important class of six-membered nitrogen heterocyclic compounds, which are widely found in natural products. The pyridine ring is also very important in organic chemistry and materials chemistry. Some pyridine compounds are often used as important intermediates and catalysts in organic synthesis and multifunctional ligands in transition metal catalysis. In addition, derivatives with pyridine as the skeleton are widely used in the treatment of various diseases. Among them, trifluoromethyl-substituted pyridine derivatives are important skeletons of drugs. The trifluoromethyl group has strong electron-withdrawing properties. Introducing it into compounds can greatly improve its metabolic stability, lipophilicity, lipophilicity and membrane permeability. In recent years, studies have found that trifluoromethylpyridine derivatives with special structures have good herbicidal, antibacterial and insecticidal biological activities, making them often used as active fragments for the synthesis of innovative pesticides. Based on the importance of trifluoromethylpyridine derivatives in pesticide chemistry, it is necessary to develop a simple and efficient method for constructing trifluoromethyl derivatives.

[0003] The traditional synthesis method of trifluoromethylpyridine is to use fluorine-chlorine exchange, which requires the use of toxic chlorine and highly corrosive hydrogen fluoride, and the reaction conditions are harsh and the requirements for reaction equipment are high. In the prior art, some researchers used the [3+3] cycloaddition reaction of oxime esters catalyzed by copper to prepare 4-trifluoromethyl-substituted and 4-pentafluoroethyl-substituted pyridine compounds respectively; some researchers used trifluoroacetic anhydride and derivatives as fluorine-containing synthetic building blocks to achieve the construction of multiple types of fluorine-containing and trifluoromethyl compounds; some researchers expanded the application range of trifluoromethyl alkynone and achieved the construction of trifluoromethylpyridine derivatives through Bohlmann-Rahtz cyclization reaction. However, the construction method of the above-mentioned trifluoromethylpyridine derivatives has the disadvantages of harsh reaction conditions and environmental pollution. Therefore, it is necessary to develop a new method for preparing trifluoromethylpyridine derivatives. Summary of the invention

[0004] In view of some deficiencies in the prior art, the present invention provides a trifluoromethylpyridine derivative and a preparation method and application thereof; α,β-Unsaturated imine is used to construct a trifluoromethylpyridine derivative, which emits blue fluorescence at a wavelength between 300-500nm. The trifluoromethylpyridine derivative has good optical properties and good antibacterial activity, and is expected to be used in the field of organic luminescent materials and pesticides, with broad application prospects; the preparation method is simple and fast, with a wide substrate range, and the raw materials used are cheap and easily available, and will not cause environmental pollution; the preparation method of the trifluoromethylpyridine derivative has the advantages of simple process, high yield, good universality, etc., and has good practicality.

[0005] In order to achieve the above technical objectives, the present invention adopts the following technical means: The present invention first provides a method for preparing a trifluoromethylpyridine derivative, the preparation method comprising: Will α，β- The sulfenyl imide, cyclopropane and catalyst Lewis acid are mixed uniformly, and the solvent is refluxed for reaction under stirring conditions. After the reaction is completed, the solvent is removed in vacuo, and the trifluoromethylpyridine derivative is obtained by elution and purification.

[0006] Preferably, the α，β- The structural formula of sulfenyl imine is shown below: ; Among them, R 1 is any one of aryl, alkyl or thienyl, R 2 It is any of trifluoromethyl, alkyl or aryl.

[0007] Preferably, the structural formula of the cyclopropane is: ; Among them, R 3 It is any one of an aryl group, an alkyl group or a styryl group.

[0008] Preferably, α，β- The dosage ratio of sulfenyl imide, cyclopropane and catalyst Lewis acid is 0.1~0.2 mmol: 0.1mmol: 0.005mmol-0.1mmol.

[0009] Preferably, the catalyst Lewis acid includes any one of SnCl2, AlCl3, AgOTf, Ni(OTf)3, Fe(OTf)3, Sc(OTf)3, Cu(OTf)3, Ce(OTf)3, Pr(OTf)3, Sm(OTf)3 and Yb(OTf)3.

[0010] Preferably, the solvent comprises any one of super dry CH3CN, super dry DCE, super dry THF, CH3OH or toluene.

[0011] Preferably, the reflux reaction is carried out at 25-150° C. for 1-12 h.

[0012] Preferably, the reflux reaction is carried out at 120° C. for 4 hours.

[0013] Preferably, the stirring speed is 300-500 r / min.

[0014] Preferably, in the elution purification process, the eluent is n-hexane and ethyl acetate, wherein the volume ratio of n-hexane to ethyl acetate is 20:1.

[0015] The present invention also provides a trifluoromethylpyridine derivative prepared by the above method, and the structural formula of the trifluoromethylpyridine derivative is as follows: ; Among them, the R 1 is any one of aryl, alkyl or thienyl; R 3 is any one of aryl, alkyl or styryl; The trifluoromethylpyridine derivative emits blue fluorescence at a wavelength between 300-500 nm.

[0016] The present invention also provides the use of the trifluoromethylpyridine derivative in preparing an organic light-emitting material.

[0017] The present invention also provides the use of the trifluoromethylpyridine derivative in the preparation of pesticides.

[0018] Preferably, the application is: inhibiting one or more of Rhizoctonia solani, Aspergillus chrysanthemi and Fusarium oxysporum.

[0019] Compared with the prior art, the present invention has the following beneficial effects: The present invention utilizes trifluoromethyl α,β- Unsaturated imine is used to construct trifluoromethylpyridine derivatives, and a new method for preparing trifluoromethylpyridine derivatives is provided. The method is simple and fast, has a wide substrate range, and the raw materials used are cheap and easy to obtain, and will not cause environmental pollution. The preparation method of the present invention has a simple process, a yield of 26%-80%, and 20 trifluoromethylpyridine derivatives are prepared, which has extremely high industrial promotion value.

[0020] The trifluoromethylpyridine derivative prepared by the method of the present invention has optical properties and is expected to be applied to organic luminescent materials. It also has good antibacterial activity, with an antibacterial rate of 30%-99% against Rhizoctonia solani, an antibacterial rate of 20%-99% against Aspergillus niger, and an antibacterial rate of 50%-99% against Fusarium oxysporum. It can be used for the synthesis of pesticides and has a good application prospect. DETAILED DESCRIPTION

[0021] The present invention is further described below in conjunction with specific examples. The following examples are only used to more clearly illustrate the technical solution of the present invention, and cannot be used to limit the scope of protection of the present invention. The experimental methods without specific conditions in the following examples are selected according to conventional methods and conditions in the art, or according to the product specifications. The reagents and raw materials without specific components in the following examples can be prepared by conventional methods or are commercially available.

[0022] The reaction principle of the present invention is: Cyclopropane ring-opens under the catalysis of Yb(OTf)3 to form a 1,3 dipole, and electron transfer occurs within the molecule. α,β -The tert-butylsulfinyl group on the unsaturated imine is removed, and the lone pair of electrons on nitrogen attacks the carbon cation to form a carbon-nitrogen bond. Dimethyl malonate is removed step by step, followed by intramolecular electron transfer and cycloaddition to form a trifluoromethyl-substituted pyridine compound.

[0023] Right now: Example 1: Preparation and performance investigation of trifluoromethylpyridine derivatives In this example, (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide was selected as α，β- Sulfenyl imide, 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester as cyclopropane is used to prepare the trifluoromethylpyridine derivative 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The specific preparation steps are as follows: (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) and Yb(OTf)3 (12.8 mg, 0.02 mmol) were placed in a 25 mL reaction tube, toluene solution was added to the reaction tube, and the mixture was refluxed at 120°C for 4 h. After the reaction was completed, toluene was removed under reduced pressure, and n-hexane and ethyl acetate in a volume ratio of 20:1 were used as eluents. The reactant was purified by flash column chromatography to obtain the trifluoromethylpyridine derivative, i.e., 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 24.0 mg and a yield rate of 73%.

[0024] The product was characterized and the results were as follows: 1H NMR (400 MHz, Chloroform-d) δ 8.72 (s,1H), 7.70 (s, 1H), 7.33–7.30 (m, 3H), 7.19 –7.17(m, 2H), 7.08 (d, J = 8.4 Hz,2H), 6.83 (d, J = 8.8 Hz, 2H), 3.80 (s, 3H). 13 C NMR (101 MHz, Chloroform-d) δ159.5, 151.3,149.0, 146.7(q, J=34.3Hz), 138.3, 137.8, 130.9, 129.2, 128.6,128.5, 123.2, 128.4, 121.6(q, J = 3.0 Hz), 120.4, 114.1, 55.2. 19 F NMR (376MHz, Chloroform-d) δ -66.49.1 HRMS(ESI) m / z calcd for C 19 H 15 OF3N (M+H) + 330.1100, found 330.1102. This indicates that 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0025] This example also uses the mycelium growth rate method to investigate the antibacterial activity of the obtained 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cystoma aureum, and Fusarium oxysporum. The investigation steps are as follows: Dissolve 5 mg of 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine in 1 mL of dimethyl sulfoxide (DMSO) to prepare a 5 mg / mL solution for later use. Take 0.75 mL of the solution and add it to 75 mL of PDA culture medium and mix well to obtain a 50 μg / mL drug-containing culture medium. After solidification, use it for later use.

[0026] Three 5-mm-diameter cakes of Rhizoctonia solani, Cystomachium chrysanthemi, and Fusarium oxysporum were placed in the drug-containing culture medium respectively, with three replicates for each treatment. Carbendazim was used as a positive control and DMSO as a negative control. The culture was carried out at 25°C for 3 days. The colony expansion diameter was measured by the cross method, and the inhibition rate was calculated.

[0027] Among them, positive control: 0.75 mL of carbendazim was added to 75 mL of liquid culture medium, shaken and poured evenly into 3 culture dishes; negative control: 0.75 mL of DMSO was added to 75 mL of liquid culture medium, shaken and poured evenly into 3 culture dishes.

[0028] After testing, the antibacterial rates of 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 70.1%, 86.5%, and 67.0%, respectively. This indicates that 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0029] Example 2: Preparation and performance investigation of trifluoromethylpyridine derivatives In this example, N-((2Z,3E)-4-(4-bromophenyl)-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfenamide was selected as α，β- Sulfenyl imide, 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester as cyclopropane is used to prepare the trifluoromethylpyridine derivative 4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The specific preparation steps are as follows: N-((2Z,3E)-4-(4-bromophenyl)-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfinamide (57.3 mg, 1.5 mmol), dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) and Yb(OTf)3 (12.8 mg, 0.02 mmol) were placed in a 25 mL reaction tube, toluene solution was added to the reaction tube, and the mixture was refluxed at 120° C. for 4 h. After the reaction was completed, toluene was removed under reduced pressure, and n-hexane and ethyl acetate in a volume ratio of 20:1 were used as eluents. The reactant was purified by flash column chromatography to obtain the trifluoromethylpyridine derivative, i.e., 4-4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 26.1 mg and a yield rate of 64%.

[0030] The product was characterized and the results were as follows: 1H NMR (400 MHz, Chloroform-d) δ 8.72 (s,1H), 7.66 (s, 1H), 7.45 (d, J= 8.4 Hz, 2H), 7.08–7.05 (m, 4H), 6.86 (d, J =9.2 Hz, 2H), 3.82 (s, 3H). 13 C NMR (101 MHz, Chloroform-d) δ 159.7, 151.5,147.7, 147.0(q,J=35.4Hz), 138.1, 136.7, 131.9, 130.9(d,J = 10.1 Hz), 130.80,128.1, 125.8, 123.0, 121.2(q, J=3.0Hz), 120.3, 114.3, 55.3. 19 F NMR (376 MHz,Chloroform-d) δ -66.55. HRMS(ESI) m / z calcd for C 19 H 14 OBrF3N (M+H) + 408.0205, found 408.0206. This indicates that 4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0031] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0032] After testing, the antibacterial rates of 4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 76.1%, 46.5%, and 61.6%, respectively. This indicates that 4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0033] Example 3: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, N-((2Z,3E)-4-(3-bromophenyl)-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfinamide (57.3 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfinamide (45.5 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) in Example 1. mmol), and the other steps were the same as in Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-(3-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(3-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 24.8 mg and a yield of 61%.

[0034] The product was characterized and the results were as follows: 1H NMR (400 MHz, Chloroform-d) δ 8.73 (s,1H), 7.67 (s, 1H), 7.46 (d, J = 8.0 Hz, 1H), 7.41 (t, J = 1.6 Hz, 1H), 7.15(t, J = 8.0 Hz, 1H), 7.09 (t, J = 2.0 Hz, 1H),7.07 (d, J = 2.4 Hz, 1H), 7.04(td, J = 8.0, 1.6 Hz, 1H), 6.88–6.84 (m, 2H), 3.81 (s, 3H). 13C NMR (101 MHz,Chloroform-d) δ 159.7, 151.4, 147.3, 146.9(q,J=35.4Hz), 139.8, 138.2, 132.0,131.5, 130.9, 130.0,128.0, 125.7, 123.0, 122.7, 121.3(q, J=3.0Hz), 120.3,114.3, 55.3.19F NMR (376 MHz, Chloroform-d) δ -66.52.HRMS(ESI)m / z calcd forC19H14OBrF6N (M+H)+ 408.0205,found 408.0205. This indicates that 4-(3-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of 4-(3-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0035] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-(3-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0036] After testing, the antibacterial rates of 4-(3-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 83.6%, 78.4%, and 65.3%, respectively. This indicates that 4-(3-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0037] Example 4: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, N-((2Z,3E)-4-(2-bromophenyl)-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfinamide (57.3 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfinamide (45.5 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) in Example 1. mmol), and the other steps were the same as in Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-(4-bromophenyl)-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(4-bromophenyl)-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 17.5 mg and a yield of 63%.

[0038] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.79 (s,1H), 7.64 (s, 1H), 7.59 (d, J = 8.0 Hz, 1H), 7.24 (m, 1H), 7.20 (m, 1H), 7.10–7.05 (m, 3H), 6.79 (d, J = 8.8 Hz, 2H), 3.77 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 159.6, 151.1, 148.2, 146.1(q, J=35.4Hz), 138.9, 138.8, 133.1,131.1, 130.6, 129.9, 128.2, 127.44, 123.1, 122.5, 122.2(q, J=3.0Hz),120.3,113.9, 55.2. 19 F NMR (376 MHz, Chloroform- d ) δ -66.52.HRMS(ESI) m / z calcd forC 19 H 14 OBrF3N (M+H) +408.0205, found 408.0209. This indicates that 4-(4-bromophenyl)-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine was successfully prepared. The structural formula of the 4-(4-bromophenyl)-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0039] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-(4-bromophenyl)-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Chrysotrichum chrysanthemi, and Fusarium oxysporum. The examination steps refer to Example 1.

[0040] After testing, the antibacterial rates of 4-(4-bromophenyl)-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 74.1%, 43.3%, and 63.6%, respectively. This indicates that 4-(4-bromophenyl)-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0041] Example 5: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this embodiment, N-((2Z,3E)-4-(4-chlorophenyl)-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfinamide (50.5 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfinamide (45.5 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) in Example 1. mmol), and the other steps were the same as in Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 22.1 mg and a yield of 61%.

[0042] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d) δ 8.72 (s,1H), 7.67 (s, 1H), 7.30 (s, 1H), 7.28 (s, 1H), 7.12 (d, J = 8.8 Hz, 2H), 7.07(d, J = 8.8 Hz, 2H), 6.86 (d, J = 8.8 Hz, 2H), 3.82 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 159.7, 151.4, 147.7, 146.9(q, J=35.4Hz), 138.2, 136.2, 134.8,130.9, 130.5,128.9, 128.2, 123.0, 121.3(q, J=3.0Hz), 120.3, 114.3, 55.3. 19 FNMR (376 MHz, Chloroform-d) δ-66.55.HRMS(ESI)m / z calcd for C 19 H 14 OClF3N (M+H) + 364.0710, found 364.0713. This indicates that 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0043] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0044] After testing, the antibacterial rates of 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 82.1%, 23.6%, and 61.3%, respectively. This indicates that 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0045] Example 6: Preparation and performance investigation of trifluoromethylpyridine derivatives In this example, N-((2Z,3E)-4-(4-trifluoromethylphenyl)-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfinamide (55.6 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-ylidene)propane-2-sulfinamide (45.5 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) in Example 1. mmol), and the other steps were the same as in Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-(4-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(4-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 28.1 mg and a yield of 71%.

[0046] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.76 (s,1H), 7.70 (d, J = 8.0 Hz, 1H), 7.59 (t, J = 7.6 Hz, 1H), 7.48 (s, 1H), 7.43 (t, J =8.0 Hz, 1H), 7.34 (d, J = 8.0 Hz, 1H), 7.08 – 7.03 (m, 2H), 6.85 (d, J = 8.8 Hz,2H), 3.81 (d, J = 4.0 Hz, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 159.8, 151.5,147.3, 147.0(q, J=35.4Hz), 138.6, 138.4, 132.6, 130.9, 129.6, 129.1, 127.8,126.0(q, J=3.0Hz), 125.6(d, J=4.0Hz),125.2(q, J=4.0Hz), 121.2(q, J=3.0Hz),114.3, 55.3(d, J=4.0Hz) 19F NMR (376MHz, Chloroform-d) δ -61.73,-66.52;HRMS(ESI)m / z calcd for C 20 H 14 OF6N (M+H) + 398.0974, found 398.0977. This indicates that 4-(4-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-(4-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0047] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-(4-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Chrysotrichum chrysanthemi, and Fusarium oxysporum. The examination steps refer to Example 1.

[0048] After testing, the antibacterial rates of 4-(4-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 72.6%, 90.0%, and 71.7%, respectively. This indicates that 4-(4-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0049] Example 7: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, N-((2Z,3E)-4-(3-trifluoromethylphenyl)-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfinamide (55.6 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-ylidene)propane-2-sulfinamide (45.5 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) in Example 1. mmol), and the other steps were the same as in Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-(3-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(3-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 23.8 mg and a yield of 60%.

[0050] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.77 (s,1H), 7.71 (s, 1H), 7.60 (d, J = 7.8 Hz, 1H), 7.48 (s, 1H), 7.43 (t, J = 7.8 Hz,1H), 7.34 (d, J = 7.8 Hz, 1H), 7.07–7.03 (m, 2H), 6.87–6.83 (m, 2H), 3.81 (s,3H). 13 C NMR (101 MHz, CDCl3) δ 159.9, 151.6, 147.5, 142.9(q, J=35.4Hz), 138.7,138.6, 132.7, 131.3(q, J=33.3Hz), 131.1, 129.3, 127.9, 126.2 (q, J = 4.0 Hz), 125.4 (q, J = 4.0 Hz), 125.2, 123.1, 122.5, 121.4 (q, J = 3.0Hz), 120.4, 114.5, 55.5. 19 F NMR (376 MHz, Chloroform-d ) δ -61.72, -66.51;HRMS(ESI) m / z calcd forC 20 H 14 OF6N (M+H) + 398.0974, found 398.0979. This indicates that 4-(3-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-(3-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0051] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-(3-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0052] After testing, the antibacterial rates of 4-(3-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 64.9%, 75.9%, and 57.1%, respectively. This indicates that 4-(3-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0053] Example 8: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, N-((2Z,3E)-4-(4-methoxyphenyl)-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfinamide (50.0 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-ylidene)propane-2-sulfinamide (45.5 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) in Example 1. mmol), and the other steps were the same as in Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 17.2 mg and a yield of 48%.

[0054] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.67 (s,1H), 7.68 (s, 1H), 7.12 (d, J = 2.4 Hz, 1H), 7.11 (d, J = 3.2 Hz, 2H), 7.09 (t, J= 2.0 Hz, 1H), 6.86 (s, 1H), 6.84 (s, 2H), 6.82 (s, 1H), 3.81 (s,3H), 3.81(s, 3H). 13 C NMR (101 MHz, Chloroform- d) δ 159.8, 159.5, 151.3, 148.7, 146.7(q,J=40.4Hz), 138.0, 130.9, 130.6, 129.9, 128.9, 123.2, 121.4(q, J=3.0Hz),120.5, 114.2, 114.7,55.3, 55.3. 19 F NMR (376 MHz, Chloroform-d) δ -66.52. HRMS(ESI) m / z calcd for C 20 H 17 O2F3N (M+H) + 360.1206, found 360.1208. This indicates that 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0055] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0056] After testing, the antibacterial rates of 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystomachia chrysanthemi, and Fusarium oxysporum, were 89.5%, 37.6%, and 64.6%, respectively. This indicates that 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0057] Example 9: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, N-((2Z,3E)-4-(3-methoxyphenyl)-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfinamide (50.0 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-ylidene)propane-2-sulfinamide (45.5 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) in Example 1. mmol), and the other steps were the same as in Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with an output of 22.6 mg and a yield of 63%.

[0058] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.72 (s,1H), 7.71 (s, 1H), 7.22 (t, J = 8.0 Hz, 1H), 7.11 (t, J = 2.4 Hz, 1H), 7.09 (t, J =2.4 Hz, 1H), 6.88-6.85 (m, 2H), 6.83 (t, J = 2.4 Hz, 1H), 6.78-6.75 (m, 1H), 6.70 (t, J = 1.6Hz, 1H), 3.80 (s, 3H), 3.67 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 159.6, 151.3, 148.9, 146.7(q, J=34.3Hz), 139.1, 138.2, 130.9,129.7, 128.6, 125.9, 123.2, 121.6, 121.5(q, J=3.0Hz), 120.4, 114.6,114.3,114.1, 55.3, 55.2. 19F NMR (376 MHz, Chloroform-d) δ -66.59.HRMS(ESI)m / z calcdfor C 20 H 17 O2F3N (M+H) + 360.1206, found 360.1208. This indicates that 4-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0059] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0060] After testing, the antibacterial rates of 4-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 90.5%, 62.4%, and 66.4%, respectively. This indicates that 4-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0061] Example 10: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, N-((2Z,3E)-4-(2-methoxyphenyl)-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfinamide (50.0 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfinamide (45.5 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) in Example 1. mmol), and the other steps were the same as in Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-(2-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(2-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 9.3 mg and a yield of 26%.

[0062] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.72 (s,1H), 7.71 (s, 1H), 7.22 (t, J = 8.0 Hz, 1H), 7.11 (t, J = 2.4 Hz, 1H), 7.09 (t, J =2.4 Hz, 1H), 6.88-6.85 (m, 2H), 6.83 (t, J = 2.4 Hz, 1H), 6.78-6.75 (m, 1H), 6.70 (t, J = 1.6Hz, 1H), 3.80 (s, 3H), 3.67 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 159.6, 151.3, 148.9, 146.7(q, J=34.3Hz), 139.1, 138.2, 130.9,129.7, 128.6, 125.9, 123.2, 121.6, 121.5(q, J=3.0Hz), 120.4, 114.6,114.3,114.1, 55.3, 55.2. 19 F NMR (376 MHz, Chloroform-d) δ -66.59.HRMS(ESI)m / z calcdfor C 20 H 17 O2F3N (M+H) + 360.1206, found 360.1208. This indicates that 4-(2-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-(2-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0063] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-(2-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0064] After testing, the antibacterial rates of 4-(2-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 78.8%, 72.4%, and 61.8%, respectively. This indicates that 4-(2-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0065] Example 11: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, N-((2Z,3E)-4-(4-methylphenyl)-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfenamide (47.6 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-ylidene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol), and the other steps were consistent with Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-(4-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(4-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 19.3 mg and a yield of 56%.

[0066] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.69 (s,1H), 7.68 (s, 1H), 7.11 (d, J = 8.0 Hz, 3H), 7.07 (d, J = 8.4 Hz, 3H), 6.84 (d, J =8.8 Hz, 2H), 3.81 (s, 3H), 2.34 (s, 3H). 13 C NMR (101 MHz, Chloroform- d) δ159.5, 151.3, 149.0, 146.7(q, J=32.3Hz), 138.5, 138.1, 134.8, 130.9, 129.3,129.1, 128.8,123.2, 121.5(q, J=3.0Hz), 120.4, 114.1, 55.3, 21.2. 19 F NMR (376MHz, Chloroform-d) δ -66.56.HRMS(ESI)m / z calcd for C 20 H 17 OF3N (M+H) + 344.1256, found 344.1258. This indicates that 4-(4-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-(4-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0067] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-(4-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0068] After testing, the antibacterial rates of 4-(4-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Fusarium oxysporum, and Fusarium oxysporum, were 90.8%, 91.5%, and 64.9%, respectively. This indicates that 4-(4-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0069] Example 12: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, N-((2Z,3E)-4-(2-methylphenyl)-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfenamide (47.6 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol), and the other steps were consistent with Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-(2-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(2-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 23.7 mg and a yield of 69%.

[0070] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.76 (s,1H), 7.60 (s, 1H), 7.28–7.24 (m, 1H),7.21 (td, J = 8.0, 1.2 Hz, 1H), 7.12 (d, J =7.6 Hz, 2H), 7.07–7.02 (m, 2H), 6.80–6.75 (m, 2H), 3.77 (s, 3H), 1.86 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 159.5, 150.7, 149.3, 146.2(q,J=34.3Hz),138.8, 137.6, 135.1, 130.5, 130.4, 129.6, 128.6, 126.0, 123.1, 122.1(q, J=3.0Hz), 120.4, 117.7, 113.9, 55.2, 19.8. 19 F NMR (376 MHz, Chloroform-d) δ -66.57.HRMS(ESI)m / z calcd for C 20 H 17 OF3N (M+H) +344.1257, found 344.1253. This indicates that 4-(2-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-(2-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0071] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-(2-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Chrysotrichum chrysanthemi, and Fusarium oxysporum. The examination steps refer to Example 1.

[0072] After testing, the antibacterial rates of 4-(2-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystomachia chrysanthemi, and Fusarium oxysporum, were 93.8%, 83.8%, and 66.0%, respectively. This indicates that 4-(2-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0073] Example 13: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, N-((2Z,3E)-4-thienyl-1,1,1-trifluorobut-3-ene-2-ylidene)-2-methylpropane-2-sulfinamide (46.4 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfinamide (45.5 mg, 1.5 mmol) and dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) in Example 1, and the other steps were consistent with Example 1 to prepare the trifluoromethylpyridine derivative, i.e., 4-thienyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-thienyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 25.9 mg and a yield rate of 77%.

[0074] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.62 (s,1H), 7.83 (s, 1H), 7.35 (dd, J= 5.2, 1.6 Hz, 1H), 7.22 – 7.18 (m, 2H), 7.02(dd, J = 3.2, 1.2 Hz, 1H), 6.98 – 6.96 (m, 1H), 6.96 – 6.92 (m, 2H), 3.86 (s,3H). 13 C NMR (101 MHz, Chloroform- d ) δ 160.0, 151.8, 147.0(q, J=34.3Hz), 142.0,138.9, 137.5, 130.9, 128.9, 128.7, 128.6, 127.6,123.0, 120.3, 120.2(q, J=3.0Hz), 114.3, 55.3. 19 F NMR (376 MHz, ) δ -66.50.HRMS(ESI)m / z calcd forC 17 H 13 OSF3N (M+H) + 336.0664, found 336.0668. This indicates that 4-thienyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-thienyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0075] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-thienyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0076] After testing, the antibacterial rates of 4-thienyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 78.3%, 89.3%, and 68.0%, respectively. This indicates that 4-thienyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0077] Example 14: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, N-((1Z,2E)-1,3-diphenylallyl)-2-methylpropane-2-sulfinamide (46.6 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) and Yb(OTf)3 (12.8 mg, 0.02 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfinamide (45.5 mg, 1.5 mmol) and 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) in Example 1, and the other steps were consistent with Example 1 to prepare the trifluoromethylpyridine derivative, i.e., 2-phenyl-4-phenyl-5-(4-methoxyphenyl)pyridine. The 2-phenyl-4-phenyl-5-(4-methoxyphenyl)pyridine was a white solid with a yield of 16.2 mg and a yield rate of 48%.

[0078] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.7(s, 1H),8.07 (t, J = 1.6 Hz, 1H), 8.05 (t, J = 1.6 Hz, 1H), 7.75 (s, 1H), 7.52 – 7.47 (m,2H), 7.45 – 7.41 (m, 1H), 7.32 – 7.29(m, 3H), 7.25 – 7.22 (m, 2H), 7.13 –7.09 (m, 2H), 6.83 (t, J = 2.4 Hz, 1H), 6.81 (t, J = 2.0 Hz, 1H), 3.80 (s,3H). 13 C NMR (101 MHz, Chloroform- d ) δ 159.0, 156.1, 150.9, 148.3, 143.0,139.3, 139.1, 133.9, 130.9, 129.9, 129.3, 128.8, 128.4, 127.8, 126.9, 121.6,113.8,55.2.HRMS(ESI)m / z calcd for C 24 H 20 ON (M+H) +338.1539, found 338.1535. This indicates that 2-phenyl-4-phenyl-5-(4-methoxyphenyl)pyridine has been successfully prepared. The structural formula of the 2-phenyl-4-phenyl-5-(4-methoxyphenyl)pyridine is shown below: .

[0079] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 2-phenyl-4-phenyl-5-(4-methoxyphenyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0080] After testing, the antibacterial rates of 2-phenyl-4-phenyl-5-(4-methoxyphenyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 61.4%, 70.8%, and 65.0%, respectively. This indicates that 2-phenyl-4-phenyl-5-(4-methoxyphenyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0081] Example 15: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), dimethyl 2-(3-methoxyphenyl)cyclopropane-1,1-dicarboxylate (23.4 mg, 1.0 mmol) and Yb(OTf)3 (12.8 mg, 0.02 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol), and the other steps were consistent with Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-phenyl-5-(3-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-phenyl-5-(3-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 7.6 mg and a yield of 23%.

[0082] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.75 (s,1H), 7.73 (s, 1H), 7.34 – 7.28 (m, 3H),7.23 (d, J= 8.0 Hz, 1H), 7.20 – 7.18(m, 2H), 6.86 (dd, J = 8.4, 2.8 Hz, 1H), 6.76 (td, J = 7.6, 1.2 Hz, 1H), 6.67 –6.66 (m, 1H), 3.65 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 159.5, 151.2,149.3, 147.4(q, J=34.3Hz), 141.1, 138.4, 137.7, 137.6, 129.6,129.2, 128.6,128.6, 123.1, 122.1, 121.5(q, J=3.0Hz), 115.2, 114.0, 55.2. 19 F NMR (376 MHz, )δ -66.51.HRMS(ESI)m / zcalcd for C 19 H 15 OF3N (M+H) + 330.1100, found 330.1101. This indicates that 4-phenyl-5-(3-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-phenyl-5-(3-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0083] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-phenyl-5-(3-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0084] After testing, the antibacterial rates of 4-phenyl-5-(3-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 88.3%, 98.3%, and 72.4%, respectively. This indicates that 4-phenyl-5-(3-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0085] Example 16: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), 2-(2-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) and Yb(OTf)3 (12.8 mg, 0.02 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol), and the other steps were consistent with Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-phenyl-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-phenyl-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 16.8 mg and a yield of 51%.

[0086] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.69 (s,1H), 7.73 (s, 1H), 7.32 (td, J = 8.0, 7.5, 1.6 Hz, 1H), 7.28 – 7.26 (m, 2H), 7.25 – 7.22 (m, 1H), 7.17 (dd, J = 7.2, 2.0 Hz, 2H), 7.14 (d, J = 3.2 Hz, 1H),6.98 (td, J = 7.2, 1.2 Hz, 1H), 6.77 (d, J = 8.4 Hz, 1H), 3.37 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 156.3, 151.8, 150.4, 147.1(q, J=34.3Hz), 138.5,135.7, 131.3, 130.1, 128.3, 128.2, 128.1, 125.6, 123.2, 120.9, 120.8(q, J=3.0Hz),120.4, 111.0, 54.9. 19F NMR (376 MHz, ) δ -66.69.HRMS(ESI)m / z calcd forC 19 H 15 OF3N (M+H) + 330.1100, found 330.1105. This indicates that 4-phenyl-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-phenyl-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0087] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-phenyl-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0088] After testing, the antibacterial rates of 4-phenyl-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 82.1%, 83.6%, and 64.2%, respectively. This indicates that 4-phenyl-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0089] Example 17: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), 2-(2,6-dimethoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (29.4 mg, 1.0 mmol) and Yb(OTf)3 (12.8 mg, 0.02 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol), and the other steps were consistent with Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-phenyl-5-(2,6-dimethoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-phenyl-5-(2,6-dimethoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 16.8 mg and a yield of 51%.

[0090] The product was characterized and the results were as follows:1 H NMR (400 MHz, Chloroform- d ) δ 8.61 (s,1H), 7.72 (s, 1H), 7.25 – 7.21 (m, 4H),7.15 (d, J = 2.0 Hz, 1H), 7.14 – 7.12(m, 1H), 6.49 (s, 1H), 6.48 (s, 1H), 3.52 (s, 6H). 13 C NMR (101 MHz, Chloroform- d ) δ 157.6, 153.1, 151.2, 146.6(q, J=34.3Hz), 138.7, 131.9, 130.3,128.1, 127.9, 126.1, 123.3,120.7(q, J=3.0Hz), 120.6, 114.0, 103.8, 55.5. 19 FNMR (376 MHz, ) δ -66.51.HRMS(ESI)m / z calcd for C 20 H 17 O2F3N (M+H) + 360.1206, found 360.1208. This indicates that 4-phenyl-5-(2,6-dimethoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-phenyl-5-(2,6-dimethoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0091] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-phenyl-5-(2,6-dimethoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0092] After testing, the antibacterial rates of 4-phenyl-5-(2,6-dimethoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 33.2%, 48.0%, and 63.1%, respectively. This indicates that 4-phenyl-5-(2,6-dimethoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0093] Example 18: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), 2-(3,4-dimethoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (29.4 mg, 1.0 mmol) and Yb(OTf)3 (12.8 mg, 0.02 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol), and the other steps were consistent with Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 28.4 mg and a yield of 79%.

[0094] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.76 (s,1H), 7.71 (s, 1H), 7.35 – 7.32 (m, 2H),7.32 (dd, J = 3.2, 1.2 Hz, 1H), 7.20 (d, J = 2.0 Hz, 1H), 7.20 – 7.17 (m, 1H), 6.86 (d, J = 1.2 Hz, 2H), 6.51 (t, J = 1.2Hz, 1H), 3.89 (s, 3H), 3.55 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 151.1,149.1, 149.0, 148.7, 146.8(q, J=34.3Hz), 138.2, 137.9, 129.1, 128.7, 128.6,128.4,123.1, 122.1, 121.5(q, J=3.0Hz), 120.4, 113.2, 111.2, 55.9, 55.6. 19 F NMR(376 MHz, ) δ-66.59.HRMS(ESI)m / z calcd for C20 H 17 O2F3N (M+H) + 360.1206, found360.1207. This indicates that 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0095] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0096] After testing, the antibacterial rates of 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 86.3%, 97.7%, and 74.4%, respectively. This indicates that 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0097] Example 19: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this example, (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), 2-(2,3,4-dimethoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (32.6 mg, 1.0 mmol) and Yb(OTf)3 (12.8 mg, 0.02 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfenamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol), and the other steps were consistent with Example 1 to prepare the trifluoromethylpyridine derivative, namely 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid with a yield of 28.4 mg and a yield of 79%.

[0098] The product was characterized and the results were as follows: 1H NMR (400 MHz, Chloroform- d ) δ 8.66 (s,1H), 7.74 (s, 1H), 7.30 – 7.27 (m, 3H),7.21 (d, J = 2.0 Hz, 1H), 7.20 – 7.18(m, 1H), 6.82 (d, J = 8.4 Hz, 1H), 6.66 (d, J = 8.4 Hz, 1H), 3.88 (s, 3H), 3.71 (s, 3H), 3.43 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 154.4, 151.9, 151.1,150.1, 147.1(d,J=34.3Hz), 142.1, 138.2, 135.5, 128.6, 128.4, 128.3, 125.6,123.2, 123.0, 120.9(q, J=3.0Hz), 120.5, 107.0, 60.7, 60.4, 56.0. 19 F NMR (376MHz, ) δ -66.62.HRMS(ESI)m / z calcd for C 21 H 19 O3F3N (M+H) + 390.1312, found390.1315. This indicates that 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine is shown below: .

[0099] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0100] After testing, the antibacterial rates of 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma chrysanthemi, and Fusarium oxysporum, were 42.0%, 64.0%, and 66.0%, respectively. This indicates that 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0101] Example 20: Preparation and performance evaluation of trifluoromethylpyridine derivatives In this embodiment, (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfinamide (45.5 mg, 1.5 mmol) and 2-phenylvinylcyclopropane-1,1-dicarboxylic acid dimethyl ester (32.6 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-ene-2-methylene)propane-2-sulfinamide (45.5 mg, 1.5 mmol) and 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) in Example 1, and the other steps were consistent with Example 1 to prepare the trifluoromethylpyridine derivative, i.e., 4-phenyl-5-phenylvinyl-2-(trifluoromethyl)pyridine. The 4-phenyl-5-phenylvinyl-2-(trifluoromethyl)pyridine was a white solid with a yield of 20.8 mg and a yield rate of 64%.

[0102] The product was characterized and the results were as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 9.02 (s,1H), 7.63 (s, 1H), 7.54 – 7.51 (m, 1H), 7.50 – 7.48 (m, 2H), 7.45 – 7.43 (m,2H), 7.43 – 7.40 (m, 2H), 7.37 – 7.33 (m, 2H), 7.32 – 7.28 (m, 1H), 7.21 (d, J = 16.4 Hz, 1H), 7.05 (d, J = 16.4 Hz, 1H). 13 C NMR (101 MHz, Chloroform- d) δ148.8, 148.1, 146.5(q, J=34.3Hz), 137.1, 136.4, 134.1, 133.4, 129.2, 129.1,128.9, 128.8, 128.6, 127.0, 123.2, 121.18, 121.2(q,J=3.0Hz), 120.4. 19 F NMR(376 MHz, ) δ -66.62.HRMS(ESI)m / z calcd for C 20 H 14 F3N (M+H) + 325.1078, found 325.1075. This indicates that 4-phenyl-5-phenylvinyl-2-(trifluoromethyl)pyridine has been successfully prepared. The structural formula of the 4-phenyl-5-phenylvinyl-2-(trifluoromethyl)pyridine is shown below: .

[0103] This example also uses the mycelium growth rate method to examine the antibacterial activity of the obtained 4-phenyl-5-phenylvinyl-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Cysticercus aureus, and Fusarium oxysporum. The examination steps refer to Example 1.

[0104] After testing, the antibacterial rates of 4-phenyl-5-phenylvinyl-2-(trifluoromethyl)pyridine against three tested plant pathogens, Rhizoctonia solani, Cystoma aureum, and Fusarium oxysporum, were 91.1%, 95.5%, and 64.7%, respectively. This indicates that 4-phenyl-5-phenylvinyl-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for the preparation of pesticides.

[0105] In summary, the present invention utilizes trifluoromethyl α,β- Unsaturated imine is used to construct trifluoromethylpyridine derivatives, which provides a new method for the preparation of trifluoromethylpyridine derivatives. The method is simple and fast, has a wide range of substrates, and the raw materials used are cheap and easy to obtain, and will not cause environmental pollution. The preparation method of the present invention has the advantages of simple process, high yield, good universality, etc., and has extremely high industrial promotion value. The trifluoromethylpyridine derivative prepared by the method of the present invention has optical properties and is expected to be applied to organic light-emitting materials. It also has good antibacterial activity, with an antibacterial rate of 30%-99% against Rhizoctonia solani, an antibacterial rate of 20%-99% against Chrysosporium chrysanthemi, and an antibacterial rate of 50%-99% against Fusarium oxysporum. It can be used for the synthesis of pesticides and has a good application prospect.

[0106] The embodiments are preferred implementations of the present invention, but the present invention is not limited to the above-mentioned implementations. Any obvious improvements, substitutions or modifications that can be made by those skilled in the art without departing from the essential content of the present invention belong to the protection scope of the present invention.

Claims

1. A method for preparing a trifluoromethylpyridine derivative, characterized in that: The preparation method comprises: Will α，β- The sulfenyl imide, cyclopropane and catalyst Lewis acid are mixed uniformly, and the solvent is refluxed for reaction under stirring conditions. After the reaction is completed, the solvent is removed in vacuo, and the trifluoromethylpyridine derivative is obtained by elution and purification.

2. The method for preparing a trifluoromethylpyridine derivative according to claim 1, characterized in that: Said α，β- The structural formula of sulfenyl imine is shown below: Among them, R 1 is any one of aryl, alkyl or thienyl, R 2 is any of trifluoromethyl, alkyl or aryl; The structural formula of the cyclopropane is: ; Among them, R 3 It is any one of an aryl group, an alkyl group or a styryl group.

3. The method for preparing a trifluoromethylpyridine derivative according to claim 1, characterized in that: α，β- The dosage ratio of sulfenyl imide, cyclopropane and catalyst Lewis acid is 0.1~0.2 mmol: 0.1 mmol: 0.005mmol-0.1mmol.

4. The method for preparing a trifluoromethylpyridine derivative according to claim 1, characterized in that: The catalyst Lewis acid includes any one of SnCl2, AlCl3, AgOTf, Ni(OTf)3, Fe(OTf)3, Sc(OTf)3, Cu(OTf)3, Ce(OTf)3, Pr(OTf)3, Sm(OTf)3 and Yb(OTf)3; The solvent includes any one of super dry CH3CN, super dry DCE, super dry THF, CH3OH or toluene.

5. The method for preparing a trifluoromethylpyridine derivative according to claim 1, characterized in that: The reflux reaction conditions are: reacting at 25-150° C. for 1-12 hours.

6. The method for preparing a trifluoromethylpyridine derivative according to claim 5, characterized in that: The reflux reaction conditions are: reacting at 120° C. for 4 hours.

7. The method for preparing a trifluoromethylpyridine derivative according to claim 1, characterized in that: The stirring speed is 300-500 r / min; In the elution purification process, the eluent is n-hexane and ethyl acetate, wherein the volume ratio of n-hexane to ethyl acetate is 20:

1.

8. A trifluoromethylpyridine derivative prepared by the method according to any one of claims 1 to 7, characterized in that: The structural formula of the trifluoromethylpyridine derivative is as follows: ; Among them, the R 1 is any one of aryl, alkyl or thienyl; R 3 is any one of aryl, alkyl or styryl; The trifluoromethylpyridine derivative emits blue fluorescence at a wavelength between 300-500 nm.

9. Use of the trifluoromethylpyridine derivative according to claim 8 in the preparation of organic light-emitting materials.

10. Use of the trifluoromethylpyridine derivative according to claim 8 in the preparation of pesticides.

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