A trifluoromethyl pyridine derivative, its preparation method and use

Abstract

The application provides a trifluoromethyl pyridine derivative and a preparation method and application thereof, and belongs to the technical field of organic synthesis; the trifluoromethyl pyridine derivative is constructed by using a trifluoromethyl α,β‑ unsaturated imine, the trifluoromethyl pyridine derivative emits blue fluorescence at a wavelength of 300-500 nm, has good optical properties and good bacteriostatic activity, is expected to be used in the fields of organic light-emitting materials and pesticides, and has a wide application prospect; the preparation method is simple and fast, has a wide substrate range, uses cheap and easily available raw materials, and does not cause environmental pollution; the preparation method of the trifluoromethyl pyridine derivative has the advantages of simple process, high yield and good universality, and has good practicability.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of organic synthesis, and particularly relates to a trifluoromethyl pyridine derivative and a preparation method and application thereof. BACKGROUND

[0002] Pyridine is an important six-membered nitrogen heterocyclic compound, which widely exists in natural products. The pyridine ring is also very important in organic chemistry and material chemistry. Some pyridine compounds are often used as important intermediates, catalysts and multifunctional ligands in transition metal catalysis in organic synthesis. Moreover, 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. Trifluoromethyl has strong electron-withdrawing properties, and its introduction into a compound can greatly improve its metabolic stability, lipophilicity, lipophilicity and membrane permeability. In recent years, research has found that trifluoromethyl pyridine derivatives with special structures exhibit good biological activities such as herbicidal, antibacterial and insecticidal activities, so they are often used as active fragments for the synthesis of innovative pesticides. Based on the importance of trifluoromethyl pyridine derivatives in pesticide chemistry, it is necessary to develop a simple and efficient method for constructing trifluoromethyl derivatives.

[0003] The traditional synthesis method of trifluoromethyl pyridine is to use fluorine-chlorine exchange. This method needs to use toxic chlorine gas and strong corrosive hydrogen fluoride, and the reaction conditions are harsh and the requirements for the reaction equipment are high. In the prior art, some researchers use copper-catalyzed [3+3] cycloaddition of oxime esters to prepare 4-trifluoromethyl-substituted and 4-pentafluoroethyl-substituted pyridine compounds respectively; some researchers use trifluoroacetic anhydride and derivatives as fluorine-containing building blocks to realize the construction of multiple types of fluorine-containing and trifluoromethyl compounds; and some researchers expand the application range of trifluoromethyl alkynone, and realize the construction of trifluoromethyl pyridine derivatives through Bohlmann-Rahtz cyclization reaction. However, the above-mentioned construction methods of trifluoromethyl pyridine derivatives have the defects of harsh reaction conditions and environmental pollution. Therefore, it is necessary to develop a new preparation method of trifluoromethyl pyridine derivatives. SUMMARY

[0004] In view of some deficiencies in the prior art, the application provides a trifluoromethyl pyridine derivative and a preparation method and application thereof. α,β-Unsaturated imine is used to construct a trifluoromethylpyridine derivative. The trifluoromethylpyridine derivative emits blue fluorescence at a wavelength between 300 and 500 nm. The trifluoromethylpyridine derivative has good optical properties and excellent antibacterial activity, and is expected to be used in the fields of organic luminescent materials and pesticides, with broad application prospects. The preparation method is simple and fast, has 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:

[0006] The present invention first provides a method for preparing a trifluoromethylpyridine derivative, which comprises:

[0007] Will α，β- The sulfenyl imine, cyclopropane and catalyst Lewis acid are mixed uniformly, and the solvent is refluxed under stirring conditions for reaction. After the reaction is completed, the solvent is removed in vacuo, and the mixture is eluted and purified to obtain the trifluoromethylpyridine derivative.

[0008] Preferably, the α，β- The structural formula of sulfenyl imine is shown below:

[0009] ; Among them, R 1 is any one of aryl, alkyl or thienyl, R 2 is any of trifluoromethyl, alkyl or aryl.

[0010] Preferably, the structural formula of the cyclopropane is:

[0011] ; Among them, R 3 is any one of an aryl group, an alkyl group or a styryl group.

[0012] Preferably, α，β- The dosage ratio of sulfenyl imine, cyclopropane and catalyst Lewis acid is 0.1~0.2 mmol: 0.1 mmol: 0.005 mmol-0.1 mmol.

[0013] 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.

[0014] Preferably, the solvent comprises any one of ultra-dry CH3CN, ultra-dry DCE, ultra-dry THF, CH3OH or toluene.

[0015] Preferably, the reflux reaction is carried out at 25-150 DEG C for 1-12 h.

[0016] Preferably, the reflux reaction is carried out at 120 DEG C for 4 h.

[0017] Preferably, the stirring speed is 300-500 r / min.

[0018] Preferably, in the elution purification process, the eluent is n-hexane and ethyl acetate, and the volume ratio of n-hexane to ethyl acetate is 20:1.

[0019] The application further provides the trifluoromethyl pyridine derivative prepared by the above method, and the structural formula of the trifluoromethyl pyridine derivative is as follows: ;

[0020] wherein, R 1 is any one of aryl, alkyl or thienyl; R 3 is any one of aryl, alkyl or styryl;

[0021] The trifluoromethyl pyridine derivative emits blue fluorescence at a wavelength of 300-500 nm.

[0022] The application further provides application of the above trifluoromethyl pyridine derivative in preparation of an organic light-emitting material.

[0023] The application further provides application of the above trifluoromethyl pyridine derivative in preparation of a pesticide.

[0024] Preferably, the application is to inhibit one or more of Rhizoctonia solani, Catenaria anguillarum and Fusarium oxysporum.

[0025] Compared with the prior art, the application has the beneficial effects that:

[0026] The application uses a trifluoromethyl α,β- group to construct a trifluoromethyl pyridine derivative, and provides a new method for preparation of the trifluoromethyl pyridine derivative, the method is simple and fast, has a wide substrate range, and uses cheap and easily-obtained raw materials, and does not cause environmental pollution. The preparation method has a simple process, a yield of 26%-80%, and prepares 20 trifluoromethyl pyridine derivatives, and has extremely high industrial popularization value.

[0027] 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 inhibition rate of 30%-99% against Rhizoctonia solani, an inhibition rate of 20%-99% against Aspergillus niger, and an inhibition rate of 50%-99% against Fusarium oxysporum. It can be used in the synthesis of pesticides and has good application prospects. DETAILED DESCRIPTION

[0028] The present invention will be further described below with reference to specific examples. The following examples are only used to more clearly illustrate the technical solutions of the present invention and are not intended to limit the scope of protection of the present invention. Experimental methods in the following examples where specific conditions are not specified are performed in accordance with conventional methods and conditions in the art, or are selected according to commercial specifications. Reagents and raw materials where specific components are not specified in the following examples can be prepared by conventional methods or are commercially available.

[0029] The reaction principle of the present invention is:

[0030] Cyclopropane is ring-opened 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 the nitrogen attacks the carbon cation to form a carbon-nitrogen bond. The dimethyl malonate is removed step by step, followed by intramolecular electron transfer and cycloaddition to form a trifluoromethyl-substituted pyridine compound.

[0031] Right now:

[0032]

[0033] Example 1: Preparation and performance evaluation of trifluoromethylpyridine derivatives

[0034] 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 imine, 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:

[0035] Into a 25 mL reaction tube was placed (R)-2-methyl-N-((2Z,3E)-1,1,1- trifluoro-4-phenylbut-3-en-2-ylidene)propane-2-sulfmamide (45.5 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). Toluene was added to the reaction tube, and the reaction was refluxed at 120 °C for 4 h. After the reaction was completed, toluene was removed under reduced pressure, and the reaction was purified by flash column chromatography using n-hexane and ethyl acetate (20:1, v / v) as eluents to obtain the trifluoromethylpyridine derivative, 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was obtained as a white solid in a yield of 24.0 mg (73%).

[0036] The product was characterized, and the characterization results were as follows: 1 H 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 the 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was successfully prepared, and the structural formula of the 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is as follows:

[0037] .

[0038] The mycelium growth rate method was also used to investigate the antibacterial activity of the obtained 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine on three plant pathogenic fungi, Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum. The investigation steps are as follows:

[0039] 5 mg of 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine was dissolved in 1 mL of dimethyl sulfoxide (DMSO) to prepare a 5 mg / mL drug solution. 0.75 mL of the drug solution was added to 75 mL of PDA medium and mixed uniformly to obtain a 50 μg / mL drug-containing medium, which was solidified and reserved.

[0040] Three Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum fungus cakes with a diameter of 5 mm were placed in the drug-containing medium, respectively, with three replicates for each treatment. Carbendazim was used as a positive control, and DMSO was used as a negative control. The culture was incubated at 25°C for 3 days. The colony expansion diameter was measured by cross method, and the inhibition rate was calculated.

[0041] The positive control: 0.75 mL of carbendazim was added to 75 mL of liquid medium, shaken uniformly, and poured into three culture dishes. The negative control: 0.75 mL of DMSO was added to 75 mL of liquid medium, shaken uniformly, and poured into three culture dishes.

[0042] The test results showed that the antibacterial rates of 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine on Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum were 70.1%, 86.5%, and 67.0%, respectively. This indicated that 4-phenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine had good antibacterial activity and could be used as a raw material for preparing pesticides.

[0043] Example 2: Preparation and performance investigation of trifluoromethyl pyridine derivatives

[0044] In this example, N-((2Z,3E)-4-(4-bromophenyl)-1,1,1-trifluorobut-3-en-2-ylidene)-2-methylpropane-2-sulfmamide was selected as the starting material for the preparation of trifluoromethyl pyridine derivatives. α，β- Dimethyl 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylate was used as the starting material for the preparation of trifluoromethyl pyridine derivatives 4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine. The specific preparation steps are as follows:

[0045] N-((2Z,3E)-4-(4-bromophenyl)-1,1,1-trifluorobut-3-en-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 put into a 25 mL reaction tube, to which toluene solution was added, and the reaction 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 eluent to purify the reaction by flash column chromatography to obtain the trifluoromethyl pyridine 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, and the yield was 26.1 mg, with a yield of 64%.

[0046] The product was characterized, and the characterization results were as follows: 1 H 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, and the structural formula of the 4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is as follows:

[0047] .

[0048] The obtained 4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was also used to investigate the fungistatic activity against three plant pathogenic fungi, Rhizoctonia solani, Sclerotinia sclerotiorum and Fusarium oxysporum by mycelial growth rate method. The investigation steps refer to Example 1.

[0049] It was found that the 4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine had a fungistatic rate of 76.1%, 46.5% and 61.6% against Rhizoctonia solani, Sclerotinia sclerotiorum and Fusarium oxysporum, respectively, which indicated that the 4-(4-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine had good fungistatic activity and could be used as a raw material for preparing pesticides.

[0050] Example 3: Preparation and performance investigation of trifluoromethyl pyridine derivatives

[0051] In this example, N-((2Z,3E)-4-(3-bromophenyl)-1,1,1-trifluorobut-3-en-2-ylidene)-2-methylpropane-2-sulfmamide (57.3 mg, 1.5 mmol) and 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) were selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-en-2-ylidene)propane-2-sulfmamide (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 the same as those in Example 1 to prepare the trifluoromethyl pyridine derivative, i.e. 4-(3-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(3-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid, and the yield thereof was 24.8 mg with a yield of 61%.

[0052] 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 the 4-(3-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below:

[0053] .

[0054] This example also uses the mycelium growth rate method to investigate the antibacterial activity of the obtained 4-(3-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Chrysosporium chrysanthemi, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0055] After testing, the antibacterial rates of 4-(3-bromophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three test plant pathogens, Rhizoctonia solani, Cystoma aureum, and Fusarium oxysporum, were 83.6%, 78.4%, and 65.3%, respectively. This shows 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.

[0056] Example 4: Preparation and performance investigation of trifluoromethyl pyridine derivative

[0057] This example selected N-((2Z,3E)-4-(2-bromophenyl)-l,l,l-trifluorobut-3-en-2- ylidene)-2-methylpropane-2-sulfmamide (57.3 mg, 1.5 mmol), dimethyl 2-(4- methoxyphenyl)cyclopropane-l,l-dicarboxylate (23.4 mg, 1.0 mmol) instead of (R)-2- methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2-ylidene)propane-2-sulfmamide (45.5 mg, 1.5 mmol), dimethyl 2-(4-methoxyphenyl)cyclopropane-l,l- dicarboxylate (23.4 mg, 1.0 mmol) in Example 1, and other steps were consistent with Example 1, to prepare the trifluoromethyl pyridine 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, and its yield was 17.5 mg, the yield was 63%.

[0058] The product was characterized, and the characterization 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 is successfully prepared, and the structural formula of 4-(4-bromophenyl)-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine is as follows:

[0059] .

[0060] This example also uses the mycelial growth rate method to investigate the antibacterial activity of the obtained 4-(4-bromophenyl)-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine on three plant pathogenic fungi, Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0061] After testing, the antibacterial rates of 4-(4-bromophenyl)-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine on Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum are 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 preparing pesticides.

[0062] Example 5: Preparation and performance investigation of trifluoromethylpyridine derivatives

[0063] In this example, N-((2Z,3E)-4-(4-chlorophenyl)-1,1,1-trifluorobut-3-en-2- ylidene)-2-methylpropane-2-sulfmamide (50.5 mg, 1.5 mmol) and 2-(4- methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) are selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4- phenylbut-3-en-2-ylidene)propane-2-sulfmamide (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 are consistent with Example 1 to prepare the trifluoromethylpyridine derivative, i.e., 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is a white solid, and the yield is 22.1 mg, and the yield is 61%.

[0064] The product is characterized, and the characterization results are 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 was successfully prepared. The structural formula of the 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below:

[0065] .

[0066] This example also uses the mycelium growth rate method to investigate the antibacterial activity of the obtained 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Chrysosporium chrysanthemi, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0067] After testing, the antibacterial rates of 4-(4-chlorophenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three test plant pathogens, Rhizoctonia solani, Cystoma aureum, and Fusarium oxysporum, were 82.1%, 23.6%, and 61.3%, respectively. This shows 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.

[0068] Example 6: Preparation and performance evaluation of trifluoromethylpyridine derivatives

[0069] This example selects N-((2Z,3E)-4-(4-trifluoromethylphenyl)-l,l,l- trifluorobut-3-en-2-ylidene)-2-methylpropane-2-sulfmamide (55.6 mg, 1.5 mmol), 2-(4- methoxyphenyl)cyclopropane-l,l-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) instead of (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2-ylidene)propane-2- sulfmamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-l,l-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) in Example 1, and other steps are consistent with Example 1, to prepare the trifluoromethylpyridine derivative, i.e. 4-(4- trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-(4- trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is a white solid, and its yield is 28.1 mg, the yield is 71%.

[0070] The product was characterized, and the characterization 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 shows that the 4-(4-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine is successfully prepared, and the structural formula of the 4-(4-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine is as follows:

[0071] .

[0072] The mycelial growth rate method is also used in this example to investigate the antibacterial activity of the obtained 4-(4-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine on three plant pathogenic fungi, Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0073] After testing, the antibacterial rates of 4-(4-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine on Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum are 72.6%, 90.0%, and 71.7%, respectively. This shows that 4-(4-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine has good antibacterial activity and can be used as a raw material for preparing pesticides.

[0074] Example 7: Preparation and performance investigation of trifluoromethyl pyridine derivatives

[0075] This example selected N-((2Z,3E)-4-(3-trifluoromethylphenyl)-l,l,l- trifluorobut-3-en-2-ylidene)-2-methylpropane-2-sulfmamide (55.6 mg, 1.5 mmol), 2-(4- methoxyphenyl)cyclopropane-l,l-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) instead of (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2-ylidene)propane-2- sulfmamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-l,l-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) in Example 1, and other steps were consistent with 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, and its yield was 23.8 mg, the yield was 60%.

[0076] The product was characterized, and the characterization 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 forC20 H 14 OF6N (M+H) + 398.0974, found 398.0979.。This shows that the 4-(3-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine is successfully prepared, and the structural formula of the 4-(3-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine is as follows:

[0077] .

[0078] This example also uses the mycelial growth rate method to investigate the antibacterial activity of the obtained 4-(3-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine on three plant pathogenic fungi, Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0079] After testing, the antibacterial rates of 4-(3-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine on Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum were 64.9%, 75.9%, and 57.1%, respectively. This shows that 4-(3-trifluoromethylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine has good antibacterial activity and can be used as a raw material for preparing pesticides.

[0080] Example 8: Preparation and performance investigation of trifluoromethyl pyridine derivatives

[0081] In this example, N-((2Z,3E)-4-(4-methoxyphenyl)-1,1,1-trifluorobut-3-en-2-ylidene)-2-methylpropane-2-sulfmamide (50.0 mg, 1.5 mmol) and 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) are selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-en-2-ylidene)propane-2-sulfmamide (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 are consistent with Example 1, to prepare the trifluoromethyl pyridine derivative, i.e., 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine. The 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine is a white solid, and the yield is 17.2 mg, with a yield of 48%.

[0082] The product is characterized, and the characterization results are as follows: 1H 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 was successfully prepared. The structural formula of the 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below:

[0083] .

[0084] This example also uses the mycelium growth rate method to investigate the antibacterial activity of the obtained 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, Rhizoctonia solani, Chrysosporium chrysanthemi, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0085] The tested 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine has an inhibition rate of 89.5%, 37.6% and 64.6% on Rhizoctonia solani, Aschersonia aleyrodis and Fusarium oxysporum, respectively, which indicates that 4-(4-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine has good antibacterial activity and can be used as a raw material for preparing pesticides.

[0086] Example 9: Preparation and performance investigation of trifluoromethyl pyridine derivative

[0087] In this example, N-((2Z,3E)-4-(3-methoxyphenyl)-1,1,1-trifluorobut-3-en-2- ylidene)-2-methylpropane-2-sulfmamide (50.0 mg, 1.5 mmol) and 2-(4- methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) are selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4- phenylbut-3-en-2-ylidene)propane-2-sulfmamide (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 are the same as those in Example 1 to prepare the trifluoromethyl pyridine derivative, i.e. 4-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2- (trifluoromethyl)pyridine. The 4-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2- (trifluoromethyl)pyridine is a white solid, and the yield thereof is 22.6 mg, and the yield is 63%.

[0088] The product is characterized, and the characterization results are 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-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was successfully prepared. The structural formula of the 4-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below:

[0089] .

[0090] This example also uses the mycelium growth rate method to investigate the antibacterial activity of the obtained 4-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Chrysosporium chrysanthemi, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0091] After testing, the antibacterial rates of 4-(3-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three test plant pathogens, Rhizoctonia solani, Cystoma aureum, and Fusarium oxysporum, were 90.5%, 62.4%, and 66.4%, respectively. This shows 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.

[0092] Example 10: Preparation and performance evaluation of trifluoromethylpyridine derivatives

[0093] This example selected N-((2Z,3E)-4-(2-methoxyphenyl)-l,l,l- trifluorobut-3-en-2-ylidene)-2-methylpropane-2-sulfmamide (50.0 mg, 1.5 mmol), 2-(4- methoxyphenyl)cyclopropane-l,l-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) instead of (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2-ylidene)propane-2- sulfmamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-l,l-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) in Example 1, and other steps were consistent with Example 1, to prepare the trifluoromethyl pyridine 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, and its yield was 9.3 mg, the yield was 26%.

[0094] The product was characterized, and the characterization 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-(2-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine was successfully prepared. The structural formula of the 4-(2-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below:

[0095] .

[0096] This example also uses the mycelium growth rate method to investigate the antibacterial activity of the obtained 4-(2-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, Rhizoctonia solani, Chrysosporium chrysanthemi, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0097] After testing, the antibacterial rates of 4-(2-methoxyphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three test plant pathogens, Rhizoctonia solani, Cystoma aureum, and Fusarium oxysporum, were 78.8%, 72.4%, and 61.8%, respectively. This shows 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.

[0098] Example 11: Preparation and performance evaluation of trifluoromethylpyridine derivatives

[0099] This example selected N-((2Z,3E)-4-(4-methylphenyl)-l,l,l-trifluorobut-3-en-2- ylidene)-2-methylpropane-2-sulfmamide (47.6 mg, 1.5 mmol), dimethyl 2-(4- methoxyphenyl)cyclopropane-l,l-dicarboxylate (23.4 mg, 1.0 mmol) instead of (R)-2- methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2-ylidene)propane-2-sulfmamide (45.5 mg, 1.5 mmol), dimethyl 2-(4-methoxyphenyl)cyclopropane-l,l- dicarboxylate (23.4 mg, 1.0 mmol) in Example 1, and 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, and its yield was 19.3 mg, the yield was 56%.

[0100] The product was characterized, and the characterization 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 is successfully prepared, and the structural formula of 4-(4-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is as follows:

[0101] .

[0102] This example also uses the mycelial growth rate method to investigate the antibacterial activity of the obtained 4-(4-methylphenyl)-5-(4-methoxyphenyl)-2- (trifluoromethyl)pyridine on three plant pathogenic fungi, Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0103] After testing, the antibacterial rates of 4-(4-methylphenyl)-5-(4-methoxyphenyl)-2- (trifluoromethyl)pyridine on Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum are 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 preparing pesticides.

[0104] Example 12: Preparation and performance investigation of trifluoromethyl pyridine derivatives

[0105] In this example, N-((2Z,3E)-4-(2-methylphenyl)-1,1,1-trifluorobut-3-en-2- ylidene)-2-methylpropane-2-sulfmamide (47.6 mg, 1.5 mmol) and 2-(4- methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) are selected to replace (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4- phenylbut-3-en-2-ylidene)propane-2-sulfmamide (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 are consistent with Example 1. The trifluoromethyl pyridine derivative, i.e., 4-(2-methylphenyl)-5-(4-methoxyphenyl)-2- (trifluoromethyl)pyridine, is prepared. The 4-(2-methylphenyl)-5-(4-methoxyphenyl)-2- (trifluoromethyl)pyridine is a white solid, and the yield is 23.7 mg with a yield of 69%.

[0106] The product is characterized, and the characterization results are 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 was successfully prepared. The structural formula of the 4-(2-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine is shown below:

[0107] .

[0108] This example also uses the mycelium growth rate method to investigate the antibacterial activity of the obtained 4-(2-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Chrysosporium chrysanthemi, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0109] After testing, the antibacterial rates of 4-(2-methylphenyl)-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine against three test plant pathogens, Rhizoctonia solani, Cystoma aureum, and Fusarium oxysporum, were 93.8%, 83.8%, and 66.0%, respectively. This shows 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.

[0110] Example 13: Preparation and performance investigation of trifluoromethyl pyridine derivative

[0111] This example selected N-((2Z,3E)-4-thienyl-l,l,l-trifluorobut-3-en-2- ylidene)-2-methylpropane-2-sulfmamide (46.4 mg, 1.5 mmol), dimethyl 2-(4- methoxyphenyl)cyclopropane-l, l-dicarboxylate (23.4 mg, 1.0 mmol) instead of (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2-ylidene)propane-2- sulfmamide (45.5 mg, 1.5 mmol), dimethyl 2-(4-methoxyphenyl)cyclopropane- 1, 1 -dicarboxylate (23.4 mg, 1.0 mmol) in Example 1, and other steps were consistent with Example 1, to prepare the trifluoromethyl pyridine derivative, namely 4- thienyl-5-(4-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-thienyl-5-(4- methoxyphenyl)-2-(trifluoromethyl)pyridine was a white solid, and its yield was 25.9 mg, the yield was 77%.

[0112] The product was characterized, and the characterization 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-thiophenyl-5-(4-methoxyphenyl)-2- (trifluoromethyl) pyridine is successfully prepared, and the structural formula of 4-thiophenyl-5- (4-methoxyphenyl)-2-(trifluoromethyl) pyridine is as follows:

[0113] .

[0114] This example also uses the mycelial growth rate method to investigate the antibacterial activity of the obtained 4-thiophenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine on three plant pathogenic fungi, Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0115] After testing, the antibacterial rates of 4-thiophenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine on Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum were 78.3%, 89.3%, and 68.0%, respectively. This indicates that 4-thiophenyl-5-(4-methoxyphenyl)-2-(trifluoromethyl) pyridine has good antibacterial activity and can be used as a raw material for preparing pesticides.

[0116] Example 14: Preparation and performance investigation of trifluoromethyl pyridine derivatives

[0117] In this example, N-((1Z,2E)-1,3-diphenylallyl)-2-methylpropane-2-sulfonamide (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) are used instead of (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-en-2-ylidene)propane-2-sulfonamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) in Example 1, and the other steps are consistent with Example 1. The trifluoromethyl pyridine derivative, i.e., 2-phenyl-4-phenyl-5-(4-methoxyphenyl)pyridine, is prepared. The 2-phenyl-4-phenyl-5-(4-methoxyphenyl)pyridine is a white solid, and the yield is 16.2 mg, with a yield of 48%.

[0118] The product is characterized, and the characterization results are 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:

[0119] .

[0120] This example also uses the mycelium growth rate method to investigate the antibacterial activity of the obtained 2-phenyl-4-phenyl-5-(4-methoxyphenyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Chrysosporium chrysanthemi, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0121] After testing, the antibacterial rates of 2-phenyl-4-phenyl-5-(4-methoxyphenyl)pyridine against three test plant pathogens, Rhizoctonia solani, Cystoma aureum, and Fusarium oxysporum, were 61.4%, 70.8%, and 65.0%, respectively. This shows 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.

[0122] Example 15: Preparation and performance evaluation of trifluoromethylpyridine derivatives

[0123] This example selects (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2- ylmethyl)propane-2-sulfmamide (45.5 mg, 1.5 mmol), 2-(3-methoxyphenyl)cyclopropane-l, l- dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) and Yb(OTf)3(12.8 mg, 0.02 mmol) instead of (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2-ylmethyl)propane-2-sulfmamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-l, l-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) in Example 1, and other steps are 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 is a white solid, and its yield is 7.6 mg, the yield is 23%.

[0124] The product was characterized, and the characterization 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 is successfully prepared, and the structural formula of 4-phenyl-5- (3-methoxyphenyl)-2-(trifluoromethyl)pyridine is as follows:

[0125] .

[0126] This example also uses the mycelial growth rate method to investigate the antibacterial activity of the obtained 4-phenyl-5-(3-methoxyphenyl)-2-(trifluoromethyl)pyridine on three plant pathogenic fungi, Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0127] After testing, the antibacterial rates of 4-phenyl-5-(3-methoxyphenyl)-2-(trifluoromethyl)pyridine on Rhizoctonia solani, Sclerotinia sclerotiorum, 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 preparing pesticides.

[0128] Example 16: Preparation and performance investigation of trifluoromethylpyridine derivatives

[0129] In this example, (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2- ylmethyl)propane-2-sulfmamide (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) are used instead of (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2- ylmethyl)propane-2-sulfmamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane- 1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) in Example 1, and the other steps are consistent with Example 1 to prepare the trifluoromethylpyridine derivative, i.e., 4-phenyl-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-phenyl-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine is a white solid, and the yield is 16.8 mg, and the yield is 51%.

[0130] The product is characterized, and the characterization results are 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. 19 F 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:

[0131] .

[0132] This example also uses the mycelium growth rate method to investigate the antibacterial activity of the obtained 4-phenyl-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Chrysosporium chrysanthemi, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0133] The tested 4-phenyl-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine has an inhibition rate of 82.1%, 83.6%, and 64.2% on Rhizoctonia solani, Aschersonia aleyrodis, and Fusarium oxysporum, respectively, indicating that 4-phenyl-5-(2-methoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for preparing pesticides.

[0134] Example 17: Preparation and performance investigation of trifluoromethyl pyridine derivatives

[0135] In this example, (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-en-2- ylmethyl)propane-2-sulfmamide (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) are used instead of (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-en-2- ylmethyl)propane-2-sulfmamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane- 1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) in Example 1, and other steps are consistent with Example 1 to prepare the trifluoromethyl pyridine derivative, i.e., 4-phenyl-5-(2,6-dimethoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-phenyl-5-(2,6-dimethoxyphenyl)-2-(trifluoromethyl)pyridine is a white solid, and the yield is 16.8 mg, and the yield is 51%.

[0136] The product is characterized, and the characterization results are 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:

[0137] .

[0138] This example also uses the mycelium growth rate method to investigate 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 investigation steps refer to Example 1.

[0139] After testing, the antibacterial rates of 4-phenyl-5-(2,6-dimethoxyphenyl)-2-(trifluoromethyl)pyridine against three test plant pathogens, Rhizoctonia solani, Cystoma aureum, and Fusarium oxysporum, were 33.2%, 48.0%, and 63.1%, respectively. This shows 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.

[0140] Example 18: Preparation and performance evaluation of trifluoromethylpyridine derivatives

[0141] This example selects (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2- ylmethyl)propane-2-sulfmamide (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) instead of (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2- ylmethyl)propane-2-sulfmamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane- 1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) in Example 1, and other steps are consistent with Example 1, to prepare the trifluoromethyl pyridine derivative, namely 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine. The 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine is a white solid, and its yield is 28.4 mg, the yield is 79%.

[0142] The product was characterized, and the characterization 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 shows that the 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl) pyridine is successfully prepared, and the structural formula of the 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl) pyridine is as follows:

[0143] .

[0144] This example also uses the mycelial growth rate method to investigate the antibacterial activity of the obtained 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl) pyridine on three plant pathogenic fungi, Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0145] Through testing, the antibacterial rates of 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl) pyridine on Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium oxysporum are 86.3%, 97.7%, and 74.4%, respectively. This shows that 4-phenyl-5-(3,4-dimethoxyphenyl)-2-(trifluoromethyl) pyridine has good antibacterial activity and can be used as a raw material for preparing pesticides.

[0146] Example 19: Preparation and performance investigation of trifluoromethyl pyridine derivatives

[0147] In this example, (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2-ylidene)propane-2-sulfmamide (45.5 mg, 1.5 mmol), 2-(2,3,4-dimethoxyphenyl)cyclopropane-l,l-dicarboxylic acid dimethyl ester (32.6 mg, 1.0 mmol), and Yb(OTf)3(12.8 mg, 0.02 mmol) are selected instead of (R)-2-methyl-N-((2Z,3E)-l,l,l-trifluoro-4-phenylbut-3-en-2-ylidene)propane-2-sulfmamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-l,l-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) in Example 1, and other steps are consistent with Example 1. The trifluoromethyl pyridine derivative, i.e., 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl) pyridine, is prepared. The 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl) pyridine is a white solid, and the yield is 28.4 mg with a yield of 79%.

[0148] The product is characterized, and the characterization results are 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 was successfully prepared. The structural formula of the 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine is shown below:

[0149] .

[0150] This example also uses the mycelium growth rate method to investigate the antibacterial activity of the obtained 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine against three plant pathogens, namely, Rhizoctonia solani, Chrysosporium chrysanthemi, and Fusarium oxysporum. The investigation steps refer to Example 1.

[0151] The tested 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine has an inhibition rate of 42.0%, 64.0%, and 66.0% on Rhizoctonia solani, Aschersonia aleyrodis, and Fusarium oxysporum, respectively, indicating that 4-phenyl-5-(2,3,4-dimethoxyphenyl)-2-(trifluoromethyl)pyridine has good antibacterial activity and can be used as a raw material for preparing pesticides.

[0152] Example 20: Preparation and performance investigation of trifluoromethyl pyridine derivatives

[0153] In this example, (R)-2-methyl-N-((2Z,3E)-1,1,1-trifluoro-4-phenylbut-3-en-2- ylmethyl)propane-2-sulfmamide (45.5 mg, 1.5 mmol), 2-styrylcyclopropane-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-en-2-ylmethyl)propane-2-sulfmamide (45.5 mg, 1.5 mmol), 2-(4-methoxyphenyl)cyclopropane-1,1-dicarboxylic acid dimethyl ester (23.4 mg, 1.0 mmol) in Example 1, and other steps were consistent with Example 1, to prepare the trifluoromethyl pyridine derivative, i.e. 4-phenyl-5-styryl-2-(trifluoromethyl)pyridine. The 4-phenyl-5-styryl-2-(trifluoromethyl)pyridine was a white solid, with a yield of 20.8 mg and a yield of 64%.

[0154] The product was characterized, and the characterization 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) δ 148.8, 148.1, 146.5 (q, J = 34.3 Hz), 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 = 3.0 Hz), 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-styryl-2-(trifluoromethyl)pyridine is successfully prepared, and the structural formula of 4-phenyl-5-styryl-2-(trifluoromethyl)pyridine is as follows:

[0155] .

[0156] The mycelium growth rate method is also used in the embodiment to investigate the bacteriostatic activity of the obtained 4-phenyl-5-styryl-2-(trifluoromethyl)pyridine on three plant pathogenic fungi, i.e., Rhizoctonia solani, Sphaeropsis sapinea and Fusarium oxysporum, and the investigation steps refer to those in Embodiment 1.

[0157] It is tested that the bacteriostatic rates of 4-phenyl-5-styryl-2-(trifluoromethyl)pyridine on the three tested plant pathogenic fungi, i.e., Rhizoctonia solani, Sphaeropsis sapinea and Fusarium oxysporum, are 91.1%, 95.5% and 64.7% respectively, which indicates that 4-phenyl-5-styryl-2-(trifluoromethyl)pyridine has good bacteriostatic activity and can be used as a raw material for preparing pesticides.

[0158] In summary, the present application uses trifluoromethyl α,β- The present application provides a new method for preparing trifluoromethyl pyridine derivatives, which is simple and fast, has a wide substrate range, uses cheap and easily available raw materials and does not cause environmental pollution. The preparation method of the present application has the advantages of simple process, high yield and good universality, and has high industrial promotion value. The trifluoromethyl pyridine derivatives prepared by the method of the present application have optical properties and are expected to be applied to organic light-emitting materials. They also have good bacteriostatic activity, with a bacteriostatic rate on Rhizoctonia solani of 30%-99%, a bacteriostatic rate on Sphaeropsis sapinea of 20%-99% and a bacteriostatic rate on Fusarium oxysporum of 50%-99%. They can be used for the synthesis of pesticides and have good application prospects.

[0159] The above embodiments are preferred embodiments of the present application, but the present application is not limited to the above embodiments, and any obvious improvement, replacement or modification made by those skilled in the art without departing from the spirit of the present application shall fall within the protection scope of the present application.

Claims

1. A method for preparing a trifluoromethylpyridine derivative, characterized in that: The preparation method comprises: The α, β-sulfenyl imine, cyclopropane derivative and Lewis acid catalyst are uniformly mixed, and the solvent is refluxed under stirring conditions. After the reaction is completed, the solvent is removed in vacuo, and the product is purified by elution to obtain the trifluoromethylpyridine derivative. The structural formula of the α,β-sulfinyl imine is shown below: Among them, R 1 is any of aryl or thienyl, R 2 is trifluoromethyl; The structural formula of the cyclopropane derivative is: Among them, R 3 is either an aryl group or a styryl group; The structural formula of the trifluoromethylpyridine derivative is as follows: Among them, the R 1 is any one of aryl or thienyl; R 3 is either an aryl group or a styryl group; The catalyst Lewis acid is Yb(OTf)3.

2. The method for preparing a trifluoromethylpyridine derivative according to claim 1, wherein The usage ratio of α,β-sulfenyl imine, cyclopropane derivative and Lewis acid catalyst is 0.1-0.2 mmol: 0.1 mmol: 0.005 mmol-0.1 mmol.

3. The method for preparing a trifluoromethylpyridine derivative according to claim 1, wherein The solvent is selected from any one of ultra-dry CH3CN, ultra-dry DCE, ultra-dry THF, CH3OH or toluene.

4. The method for preparing a trifluoromethylpyridine derivative according to claim 1, wherein The reflux reaction conditions are: reaction at 25-150° C. for 1-12 hours.

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

6. The method for preparing a trifluoromethylpyridine derivative according to claim 1, wherein 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.

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