A trifluoromethyl benzothiazole tertiary alcohol derivative, and a preparation method and application thereof

Abstract

The application belongs to the technical field of chemical synthesis, and particularly relates to a trifluoromethyl-containing benzothiazole tertiary alcohol derivative, a preparation method and application thereof. 1 , R 2 are independently selected from hydrogen, C1-C3 alkyl, C1-C3 alkoxy or halogen; or R 1 , R 2 independently form a naphthalene ring with the substituted benzene ring together. The trifluoromethyl-containing benzothiazole tertiary alcohol derivative provided by the application has good bacteriostatic effect on one or more of Rhizoctonia solani, Fusarium moniliforme, Fusarium graminearum, Fusarium oxysporum and Phytophthora nicotianae.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of chemical synthesis, and particularly relates to a trifluoromethyl-containing benzothiazole tertiary alcohol derivative, a preparation method and application thereof. BACKGROUND

[0002] Benzothiazole is an important heterocyclic structure, and is an important chemical and pharmaceutical intermediate due to rich electrons on the ring. Derivatives thereof have diverse biological activities, have attracted extensive attention of people, and have been deeply researched. The derivatives are bacteriostatic agents such as benthiavalicarb, and the structure of benthiavalicarb is as shown in the following formula:

[0003]

[0004] The results of the benthiavalicarb are as shown in the following formula:

[0005]

[0006] The above structures all contain benzothiazole structural units, but excessive use of the bacteriostatic agents also causes some negative problems, for example, disease resurgence caused by drug resistance, and the bacteriostatic effect of the currently used bacteriostatic agents gradually decreases. In order to further meet the requirement of high bacteriostatic rate of the bacteriostatic agents, new compounds need to be developed for development of new bacteriostatic agents. SUMMARY

[0007] In order to solve the above problems, the application provides a trifluoromethyl-containing benzothiazole tertiary alcohol derivative, a preparation method and application thereof. The benzothiazole active substructure is introduced into the trifluoromethyl tertiary alcohol skeleton structure, a series of new benzothiazole compounds are designed and synthesized, the agricultural pathogenic bacteria have good inhibition effect, which is conducive to further development of bacteriostatic agents with high bacteriostatic property, and meets the use requirement.

[0008] In addition, in the existing method for developing the bacteriostatic agents, a catalyst needs to be used in the synthesis process, and the reaction condition is harsh, which is not conducive to large-scale production and application. When the new compounds are developed, not only the performance of the prepared compound needs to be concerned, but also the synthesis method needs to be simple and operable, so that the compound has the prospect of large-scale industrial production and application. For this reason, the compound with good performance and simple preparation method also needs to be further researched. The application provides a preparation method of the trifluoromethyl-containing benzothiazole tertiary alcohol derivative. In the preparation process, no catalyst is used, the reaction condition is mild, the process is simple, and the method is easy to implement, and is very suitable for large-scale production and application. The simple method support is provided for further research on the derivative.

[0009] The application is implemented through the following technical scheme.

[0010] This invention provides a trifluoromethylbenzothiazole tertiary alcohol derivative, the structural formula of which is:

[0011]

[0012] Among them, R 1 R 2 Each of the following is independently selected from hydrogen, C1-C3 alkyl, C1-C3 alkoxy, or halogen; or, R 1 R 2 Each of the substituted benzene rings independently forms a naphthalene ring.

[0013] Preferably, the alkyl group is methyl, the alkoxy group is methoxy, and the halogen is fluorine, chlorine, or bromine.

[0014] Preferred, R 1 Selected from hydrogen, methyl, fluorine, chlorine, bromine, or forming a naphthalene ring with the substituted benzene ring; R 2 It is selected from hydrogen, methoxy, chlorine, bromine, or forms a naphthalene ring with the substituted benzene ring.

[0015] Preferably, the following compounds are used:

[0016]

[0017]

[0018]

[0019] This invention provides a method for preparing the above-mentioned trifluoromethylbenzothiazole tertiary alcohol derivatives, comprising the following steps:

[0020] Using compounds of Formula 1 and Formula 2 as raw materials and sulfolane as solvent, the trifluoromethylbenzothiazole tertiary alcohol derivatives shown in Formula 3 were prepared by carbon-hydrogen bond functionalization.

[0021] The synthetic route is shown below:

[0022]

[0023] Among them, R 1 R 2 Each of the following is independently selected from hydrogen, C1-C3 alkyl, C1-C3 alkoxy, or halogen; or, R 1 R 2 Each of the substituted benzene rings independently forms a naphthalene ring.

[0024] Preferably, the molar ratio of compound 1 to compound 2 is 1:1.

[0025] Preferably, the reaction is carried out by stirring at a temperature of 120℃~130℃ for 4h~13h.

[0026] Preferably, the temperature is 120 DEG C, and the reaction time is 8-12 hours.

[0027] Preferably, after the reaction, the product can be purified by column chromatography.

[0028] The application provides application of the above-mentioned trifluoromethyl-containing benzothiazole tertiary alcohol derivative or the pesticide-acceptable salt thereof in preparation of an agricultural bacteriostatic agent for inhibiting one or more of Rhizoctonia solani, Fusarium decemellum, Fusarium graminearum, Fusarium oxysporum and Phytophthora nicotianae.

[0029] Compared with the prior art, the application has the following beneficial effects:

[0030] The application provides a trifluoromethyl-containing benzothiazole tertiary alcohol derivative.

[0031] The application introduces a benzothiazole active substructure into a trifluoromethyl tertiary alcohol skeleton structure by using sulfolane as a solvent, and the reaction process does not need to use an additional catalyst. BRIEF DESCRIPTION OF DRAWINGS

[0032] Figure 1 High resolution mass spectrum of compound 3ab.

[0033] Figure 2 High resolution mass spectrum of compound 3ac.

[0034] Figure 3 High resolution mass spectrum of compound 3ad.

[0035] Figure 4 High resolution mass spectrum of compound 3ae.

[0036] Figure 5 High resolution mass spectrum of compound 3af.

[0037] Figure 6 High resolution mass spectrum of compound 3ba.

[0038] Figure 7 High resolution mass spectrum of compound 3bb.

[0039] Figure 8 High resolution mass spectrum of compound 3bc.

[0040] Figure 9 High resolution mass spectrum for compound 3be.

[0041] Figure 10 High resolution mass spectrum for compound 3bf.

[0042] Figure 11 High resolution mass spectrum for compound 3ca.

[0043] Figure 12 High resolution mass spectrum for compound 3cd.

[0044] Figure 13 High resolution mass spectrum for compound 3ce.

[0045] Figure 14 High resolution mass spectrum for compound 3cf.

[0046] Figure 15 High resolution mass spectrum for compound 3da.

[0047] Figure 16 High resolution mass spectrum for compound 3dc.

[0048] Figure 17 High resolution mass spectrum for compound 3dd.

[0049] Figure 18 High resolution mass spectrum for compound 3ea.

[0050] Figure 19 High resolution mass spectrum for compound 3ec.

[0051] Figure 20 High resolution mass spectrum for compound 3ed.

[0052] Figure 21 High resolution mass spectrum for compound 3ef.

[0053] Figure 22 High resolution mass spectrum for compound 3eg.

[0054] Figure 23 High resolution mass spectrum for compound 3eh.

[0055] Figure 24 High resolution mass spectrum for compound 3fa.

[0056] Figure 25 High resolution mass spectrum for compound 3ga.

[0057] Figure 26 High resolution mass spectrum for compound 3ha.

[0058] Figure 27Colorless crystal structure of compound 3ea. DETAILED DESCRIPTION

[0059] In order to make the skilled in the art better understand the technical solutions of the present application can be implemented, the following specific examples and drawings of the present application are further described, but the examples are not as a limitation of the present application. The experimental methods and detection methods described in the following examples, such as no special instructions, are conventional methods; the reagents and materials, such as no special instructions, can be purchased on the market.

[0060] The present application provides a kind of containing trifluoromethyl benzothiazole tertiary alcohol derivative, the structure formula of the containing trifluoromethyl benzothiazole tertiary alcohol derivative is as shown in formula 3:

[0061]

[0062] Wherein, R 1 , R 2 Respectively independently selected from hydrogen, C1 ~ C3 alkyl, C1 ~ C3 alkoxy or halogen;Or, R 1 , R 2 Respectively independently with substituted benzene ring constitutes naphthalene ring.

[0063] Preferably, alkyl is methyl, alkoxy is methoxy, halogen is fluorine, chlorine or bromine.Further, R 1 Selected from hydrogen, methyl, fluorine, chlorine, bromine or with substituted benzene ring constitutes naphthalene ring;R 2 Selected from hydrogen, methoxy, chlorine, bromine or with substituted benzene ring constitutes naphthalene ring.

[0064] The present application provides a kind of containing trifluoromethyl benzothiazole tertiary alcohol derivative preparation method, comprising the following steps:

[0065] With formula 1 compound and formula 2 compound as raw material, with sulfolane as solvent, by reaction, the preparation of formula 3 shown containing trifluoromethyl benzothiazole tertiary alcohol derivative.

[0066] Its synthetic route is as shown below:

[0067]

[0068] Wherein, R 1 , R 2 Respectively independently selected from hydrogen, C1 ~ C3 alkyl, C1 ~ C3 alkoxy or halogen;Or, R 1 , R 2 Respectively independently with substituted benzene ring constitutes naphthalene ring.

[0069] In the preferred embodiment of the present application, the molar ratio of formula 1 compound and formula 2 compound is 1:1.

[0070] In the preferred embodiment of the present application, the reaction is stirred at a temperature of 120-130℃ for 4-13h.

[0071] In the preferred embodiment of the present application, the temperature is 120℃, and the reaction time is 8-12h.

[0072] In the preferred embodiment of the present application, after the reaction is completed, the product can be purified by column chromatography. In the present application, the active substructure of benzothiazole is introduced into the trifluoromethyl tertiary alcohol skeleton structure by a simple method using sulfolane as the solvent. In the reaction process, no additional catalyst is needed, only the raw materials need to be mixed and stirred at elevated temperature, the whole reaction is simple, easy to operate, and very conducive to large-scale production application, and provides a method support for further development of new agricultural bacteriostatic agents.

[0073] The following will be specifically described by the following.

[0074] Test Example 1-Test Example 16

[0075] The present application uses the compound shown as formula 1a and the compound shown as formula 2b as raw materials, changes the reaction conditions to prepare the product, and selects the appropriate reaction conditions through the yield, test example 1-test example 16 corresponds to group 1-16 in table 1, and the specific selection conditions and yield are shown in table 1, and the synthesis route is as follows:

[0076]

[0077] Table 1 reaction condition screening

[0078]

[0079]

[0080] a Reaction condition 1a (1.0 mmol), 2b (1.0 mmol), solvent (10 mL). b Liquid yield c No reaction d Separation yield.

[0081] As can be seen from table 1, the reaction does not need to use a catalyst, and at a temperature of 120-130℃, the reaction is stirred for 4-13h, and high yield products can be obtained, further, the optimal reaction condition is that compound 1a (1 mmol) and compound 2b (1 mmol) are mixed, sulfolane (10 mL) is used as the solvent, and the obtained compound is purified by column chromatography after stirring at 120℃ for 12 hours, to obtain the target compound 3ab.

[0082] Example 1-Example 26

[0083] Under the above optimized reaction conditions, the reaction substrates were changed to obtain different products. Compound 1 (1 mmol) and compound 2 (1 mmol) were mixed, sulfolane (10 mL) was used as the solvent, and stirring was performed at 120 °C for 12 hours. The obtained compound was purified by column chromatography to obtain the target compound 3. The reaction substrates and the yield are shown in Table 2, and examples 1-26 correspond to groups 1-26 in Table 2.

[0084] The specific synthesis route is shown as follows:

[0085]

[0086] Table 2 Different reaction substrates and corresponding yields

[0087]

[0088]

[0089] The structure data of the above compounds are given below, and the structure is shown as follows: Figures 1-26

[0090]

[0091] Compound 3ab. PE: EA = 5: 1, R f = 0.43, yellow solid, mp: 158.3-159.8 °C. 1 HNMR (400 MHz, DMSO-d6) δ 8.43 (s, 1H), 7.98 (dt, J = 3.8, 1.9 Hz, 2H), 7.89-7.78 (m, 2H), 7.66 (dd, J = 9.0, 2.7 Hz, 1H), 7.47 (dd, J = 9.0, 2.2 Hz, 1H), 7.37 (dtd, J = 24.7, 7.3, 1.4 Hz, 2H), 4.68 (d, J = 14.7 Hz, 1H), 3.79 (d, J = 14.8 Hz, 1H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 37.03, 75.41 (q, J = 29.3 Hz), 118.39, 119.89, 122.45, 122.73, 124.50, 125.38 (q, J = 288.8 Hz), 125.52, 126.50, 128.81, 129.10, 133.02, 135.43, 144.60, 152.47, 158.19, 164.35 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.13 ppm. HRMS (ESI): m / z calcd for C 19 H 11 ​ClF3NO3S [M+H] + 426.0179, found 426.0175.

[0092]

[0093] Compound 3ac. PE:EA = 5:1, R f = 0.47, yellowish solid, mp: 187.2-188.9 °C. 1 HNMR (400 MHz, DMSO-d6) δ 8.42 (s, 1H), 8.10 (d, J = 2.4 Hz, 1H), 7.97 (d, J = 7.9 Hz, 1H), 7.88 - 7.72 (m, 3H), 7.44 - 7.29 (m, 3H), 4.68 (d, J = 14.7 Hz, 1H), 3.79 (d, J = 14.8 Hz, 1H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 37.05, 75.42 (q, J = 29.1 Hz), 116.93, 118.64, 120.39, 122.44, 122.73, 124.46, 125.39 (q, J = 288.9 Hz), 125.51, 126.49, 131.80, 135.43, 135.78, 144.52, 152.47, 152.89, 158.14, 164.36 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.12 ppm. HRMS (ESI): m / z calcd for C 19 H 11 BrF3NO3S [M+H] + 469.9673, found 469.9678.

[0094]

[0095] Compound 3ac. PE:EA = 5:1, R f = 0.4, yellowish solid, mp: 167.1-168.9 °C. 1 HNMR (400 MHz, DMSO-d6) δ 8.42 (s, 1H), 8.10 (d, J = 2.4 Hz, 1H), 7.97 (d, J = 7.9 Hz, 1H), 7.88 - 7.72 (m, 3H), 7.44 - 7.29 (m, 3H), 4.68 (d, J = 14.7 Hz, 1H), 3.79 (d, J = 14.8 Hz, 1H) ppm. 13C NMR (101 MHz, DMSO-d6) δ 37.17, 56.57, 75.36 (q, J = 29.0 Hz), 115.48, 119.09, 120.74, 122.46, 122.74, 123.22, 125.30, 125.48 (q, J = 289.2 Hz), 125.50, 126.48, 135.48, 143.17, 145.99, 146.62, 152.45, 158.38, 164.47 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.31 ppm. HRMS (ESI): m / z calcd for C 20 H 14 F3NO4S [M - H] - 420.05174, found 420.04697.

[0096]

[0097] Compound 3ae. (PE:EA = 5: 1, R f = 0.47, yellow-green solid, mp: 166.5-168.2 °C) 1 HNMR (400 MHz, DMSO-d6) δ 8.41 (s, 1H), 7.96 (d, J = 2.8 Hz, 2H), 7.85 (s, 1H), 7.81 (d, J = 8.0 Hz, 1H), 7.65 (dd, J = 8.9, 2.6 Hz, 1H), 7.46 (d, J = 8.9 Hz, 1H), 7.40 (t, J = 7.6 Hz, 1H), 7.36 - 7.30 (m, 1H), 4.67 (d, J = 14.7 Hz, 1H), 3.79 (d, J = 14.8 Hz, 1H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 37.17, 56.57, 75.36 (q, J = 29.0 Hz), 115.48, 119.09, 120.74, 122.46, 122.74, 123.22, 125.30, 125.48 (q, J = 289.2 Hz), 125.50, 126.48, 135.48, 143.17, 145.99, 146.62, 152.45, 158.38, 164.47 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.31 ppm. HRMS (ESI): m / z calcd for C 19 H 11 ClF3NO3S [M + H] +426.0179, found 426.0183.

[0098]

[0099] Compound 3af. PE:EA = 5:1, R f = 0.33, white solid, mp: 212.1-213.9 °C. 1 H NMR (400 MHz, DMSO-d6) δ 9.11 (s, 1H), 8.40 (d, J = 8.5 Hz, 1H), 8.23 (d, J = 9.1 Hz, 1H), 8.04 (d, J = 8.1 Hz, 1H), 7.94 (d, J = 7.2 Hz, 1H), 7.84 (d, J = 15.8 Hz, 1H), 7.73 (t, J = 7.7 Hz, 1H), 7.61 (t, J = 8.0 Hz, 2H), 7.37 (t, J = 7.7 Hz, 1H), 7.32 - 7.25 (m, 1H), 4.78 (d, J = 14.7 Hz, 1H), 3.85 (d, J = 14.7 Hz, 1H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 37.19, 75.75 (q, J = 29.1 Hz), 112.46, 116.73, 122.21, 122.28, 122.44, 122.73, 125.46, 125.56 (q, J = 289.0 Hz), 126.45, 126.86, 129.00, 129.32, 129.54, 130.39, 135.03, 135.50, 140.93, 152.43, 154.01, 158.74, 164.57 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.34 ppm. HRMS (ESI): m / z calcd for C 23 H 14 F3NO3S [M-H] - 440.05682, found 440.05161.

[0100]

[0101] Compound 3ba. PE:EA = 5:1, R f = 0.37, pale yellow solid, mp: 157.5-159.1 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.46 (s, 1H), 8.21 (s, 1H), 7.90-7.70 (m, 3H), 7.64-7.24 (m, 4H), 4.72 (d, J = 14.8 Hz, 1H), 3.81 (d, J = 14.8 Hz, 1H) ppm. 13 CNMR (101 MHz, DMSO-d6) δ 37.25, 75.32 (q, J = 29.2 Hz), 116.29, 118.23, 118.52, 122.93, 124.22, 124.96, 125.24, 125.45 (q, J = 289.1 Hz), 129.55, 129.77, 133.42, 137.53, 145.84, 151.44, 153.85, 158.65, 165.70 ppm. 19 FNMR (377 MHz, DMSO-d6) δ -77.31 ppm. HRMS (ESI): m / z calcd for C 19 H 11 BrF3NO3S[M+H] + 469.9673, found 469.9673.

[0102]

[0103] Compound 3bb. PE:EA = 5:1, R f = 0.5, yellow solid, mp: 185.6-186.9 °C. 1 HNMR (400 MHz, DMSO-d6) δ 8.43 (s, 1H), 8.22 (d, J = 2.1 Hz, 1H), 7.94 (t, J = 3.0 Hz, 1H), 7.88 (s, 1H), 7.73 (d, J = 8.7 Hz, 1H), 7.60 (ddd, J = 9.1, 4.9, 2.6 Hz, 1H), 7.53-7.39 (m, 2H), 4.68 (d, J = 14.8 Hz, 1H), 3.80 (d, J = 14.8 Hz, 1H) ppm. 13 CNMR (101 MHz, DMSO-d6) δ 37.12, 75.34 (q, J = 29.4 Hz), 118.24, 118.33, 119.87, 124.23, 125.33 (q, J = 289.1 Hz), 124.35, 124.97, 128.79, 129.10, 129.58, 132.97, 137.50, 144.70, 151.46, 152.47, 158.16, 165.57 ppm. 19F NMR (377 MHz, DMSO-d6) δ -77.14 ppm. HRMS (ESI): m / z calcd for C 19 H 10 BrClF3NO3S[M+H] + 503.9284, found 503.9286.

[0104]

[0105] Compound 3bc. PE:EA = 5: 1, R f = 0.48, yellow solid, mp: 182.1-184.3 °C. 1 HNMR (400 MHz, DMSO-d6) δ 8.42 (s, 1H), 8.21 (s, 1H), 8.07 (s, 1H), 7.87 (s, 1H), 7.73 (d, J = 8.4 Hz, 2H), 7.48 (d, J = 7.0 Hz, 1H), 7.37 (d, J = 9.0 Hz, 1H), 4.68 (d, J = 14.8 Hz, 1H), 3.79 (d, J = 14.8 Hz, 1H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 37.13, 75.34 (q, J = 29.4 Hz), 116.91, 118.24, 118.59, 120.36, 124.23, 124.30, 124.96, 125.34 (q, J = 289.0 Hz), 129.57, 131.78, 135.74, 137.49, 144.63, 151.46, 152.88, 158.12, 165.57 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.14 ppm. HRMS (ESI): m / z calcd for C 19 H 10 Br2F3NO3S[M+H] + 547.8778, found 547.8776.

[0106]

[0107] Compound 3bc. PE:EA = 5: 1, R f = 0.47, yellow solid, mp: 186.2-188.4 °C. 1HNMR (400 MHz, DMSO-d6) δ 8.42 (s, 1H), 8.27 (d, J = 2.0 Hz, 1H), 7.98 (d, J = 2.6 Hz, 1H), 7.87 (s, 1H), 7.75 (d, J = 8.7 Hz, 1H), 7.67 (dd, J = 8.9, 2.6 Hz, 1H), 7.54 (dd, J = 8.7, 2.1 Hz, 1H), 7.47 (d, J = 8.9 Hz, 1H), 4.66 (d, J = 14.8 Hz, 1H), 3.78 (d, J = 14.8 Hz, 1H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 37.12, 75.34 (q, J = 29.2 Hz), 118.27, 118.41, 119.88, 124.29, 124.37, 125.04, 125.33 (q, J = 289.0 Hz), 128.83, 129.13, 129.65, 133.07, 137.50, 144.68, 151.47, 152.48, 158.16, 165.60 ppm. 19 FNMR (377 MHz, DMSO-d6) δ -77.10 ppm. HRMS (ESI): m / z calcd for C 19 H 10 BrClF3NO3S[M+H] + 503.9284, found 503.9286.

[0108]

[0109] Compound 3bf. PE:EA = 5:1, R f = 0.33, white solid, mp: 256.7-258.2 °C. 1 HNMR (400 MHz, DMSO-d6) δ 9.12 (s, 1H), 8.40 (d, J = 8.5 Hz, 1H), 8.22 (d, J = 9.1 Hz, 2H), 8.04 (d, J = 8.1 Hz, 1H), 7.90 (s, 1H), 7.74 (t, J = 10.0 Hz, 1H), 7.61 (t, J = 9.9 Hz, 1H), 7.50 (d, J = 8.8 Hz, 1H), 4.77 (d, J = 14.8 Hz, 1H), 3.84 (d, J = 14.8 Hz, 1H) ppm. 13C NMR (101 MHz, DMSO-d6) δ 37.26, 75.66 (q, J = 29.2 Hz), 112.46, 116.72, 118.21, 122.04, 122.27, 124.27, 125.02, 125.51 (q, J = 288.9 Hz), 126.87, 129.00, 129.33, 129.54, 129.58, 130.39, 135.08, 137.56, 141.04, 151.42, 154.03, 158.71, 165.81 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.35 ppm. HRMS (ESI): m / z calcd for C 23 H 13 BrF3NO3S [M+H] + 519.9830, found 519.9830.

[0110]

[0111] Compound 3ca. PE:EA = 5: 1, R f = 0.4, yellowish solid, mp: 184.5-186.3 °C. 1 H NMR (400 MHz, DMSO-d6) δ 8.46 (s, 1H), 8.00 (s, 1H), 7.91 (d, J = 8.5 Hz, 1H), 7.85 (s, 1H), 7.78 (d, J = 7.7 Hz, 1H), 7.56 (t, J = 7.9 Hz, 1H), 7.40 (dd, J = 21.0, 8.1 Hz, 2H), 7.27 (t, J = 7.5 Hz, 1H), 4.75 (d, J = 14.6 Hz, 1H), 3.84 (d, J = 14.7 Hz, 1H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 37.26, 75.66 (q, J = 29.2 Hz), 112.46, 116.72, 118.21, 122.04, 122.27, 124.27, 125.02, 125.51 (q, J = 288.9 Hz), 126.87, 129.00, 129.33, 129.54, 129.58, 130.39, 135.08, 137.56, 141.04, 151.42, 154.03, 158.71, 165.81 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.35 ppm. HRMS (ESI): m / z calcd for C 19 H 11 BrF3NO3S [M+H]+ 469.9673, found 469.9678.

[0112]

[0113] Compound 3cd. PE:EA = 5:1, R f = 0.28, yellowish solid, mp: 207.4-208.6 °C. 1 H NMR (400 MHz, DMSO-d6) δ 8.42 (s, 1H), 8.04 (s, 1H), 7.94 (d, J = 8.5 Hz, 1H), 7.83 (s, 1H), 7.47 (d, J = 8.5 Hz, 1H), 7.33 (d, J = 7.4 Hz, 1H), 7.29 - 7.18 (m, 2H), 4.72 (d, J = 14.7 Hz, 1H), 3.88 (s, 3H), 3.81 (d, J = 14.7 Hz, 1H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 37.31, 56.51, 75.29 (q, J = 29.1 Hz), 115.42, 119.07, 119.33, 120.72, 123.00, 124.29, 125.13, 125.26, 125.43 (q, J = 289.0 Hz), 128.25, 134.75, 143.18, 146.16, 146.59, 153.64, 158.37, 166.91 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.35 ppm. HRMS (ESI): m / z calcd for C 20 H 13 BrF3NO4S [M+H] + 499.9779, found 499.9782.

[0114]

[0115] Compound 3cd. PE:EA = 5:1, R f = 0.5, yellowish solid, mp: 176.6-177.5 °C. 1 H NMR (400 MHz, DMSO-d6) δ 8.43 (s, 1H), 8.02 (s, 1H), 7.98 - 7.92 (m, 2H), 7.88 (s, 1H), 7.63 (d, J = 8.9 Hz, 1H), 7.47 (dd, J = 12.7, 8.6 Hz, 2H), 4.69 (d, J = 14.8 Hz, 1H), 3.81 (d, J = 14.9 Hz, 1H) ppm.13 CNMR (101 MHz, DMSO-d6) δ 37.20, 75.36 (q, J = 29.4 Hz), 118.39, 119.34, 119.87, 124.29, 125.14, 125.33 (q, J = 289.0 Hz), 128.28, 128.82, 129.12, 133.04, 134.71, 144.75, 152.49, 153.68, 158.16, 166.81 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.15 ppm. HRMS (ESI): m / z calcd for C 19 H 10 BrClF3NO3S [M+H] + 503.9284, found 503.9285.

[0116]

[0117] Compound 3cf. PE:EA = 5:1, R f = 0.43, yellowish solid, mp: 186.5-187.8 °C. 1 H NMR (400 MHz, DMSO-d6) δ 9.12 (s, 1H), 8.39 (d, J = 8.4 Hz, 1H), 8.20 (d, J = 9.0 Hz, 1H), 8.01 (d, J = 9.9 Hz, 2H), 7.90 (d, J = 9.5 Hz, 2H), 7.72 (t, J = 7.8 Hz, 1H), 7.59 (t, J = 9.4 Hz, 2H), 7.43 (d, J = 8.6 Hz, 1H), 4.79 (d, J = 14.7 Hz, 1H), 3.87 (d, J = 14.8 Hz, 1H) ppm. 13 CNMR (101 MHz, DMSO-d6) δ 37.20, 75.36 (q, J = 29.4 Hz), 118.39, 119.34, 119.87, 124.29, 125.14, 125.33 (q, J = 289.0 Hz), 128.28, 128.82, 129.12, 133.04, 134.71, 144.75, 152.49, 153.68, 158.16, 166.81 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.15 ppm. HRMS (ESI): m / z calcd for C 23 H 13BrF3NO3S [M+H] + 519.9830, found 519.9828.

[0118]

[0119] Compound 3da. PE:EA = 5: 1, R f = 0.47, yellow-green solid, mp: 175.7-177.2 °C. 1 HNMR (400 MHz, DMSO-d6) δ 8.46 (s, 1H), 8.01 (d, J = 8.5 Hz, 1H), 7.90 (d, J = 2.0 Hz, 1H), 7.87-7.77 (m, 2H), 7.70-7.55 (m, 1H), 7.46-7.28 (m, 3H), 4.72 (d, J = 14.7 Hz, 1H), 3.82 (d, J = 14.8 Hz, 1H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 37.35, 75.33 (q, J = 29.2 Hz), 116.35, 118.53, 122.17, 122.88, 123.97, 125.31, 125.44 (q, J = 289.1 Hz), 125.64, 129.75, 129.82, 131.31, 133.52, 133.59, 134.29, 145.89, 153.31, 153.86, 158.65, 167.16 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.31 ppm. HRMS (ESI): m / z calcd for C 19 H 11 ClF3NO3S [M+H] + 426.0179, found 426.0184.

[0120]

[0121] Compound 3da. PE:EA = 5: 1, R f = 0.48, white solid, mp: 164.5-166.1 °C. 1 HNMR (400 MHz, DMSO-d6) δ 8.45 (d, J = 7.3 Hz, 1H), 8.07-7.92 (m, 2H), 7.91-7.77 (m, 2H), 7.67-7.54 (m, 1H), 7.50-7.21 (m, 1H), 4.70 (d, J = 14.7 Hz, 1H), 3.82 (d, J = 14.8 Hz, 1H) ppm. 13C NMR (101 MHz, DMSO-d6) δ 37.21, 75.35 (q, J = 29.6 Hz), 116.32, 118.34, 122.16, 123.92, 125.60, 125.62, 127.53 (q, J = 455.7 Hz), 128.79, 129.10, 131.31, 132.98, 134.25, 144.78, 152.47, 153.32, 153.85, 158.17, 158.64, 167.01 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.34, -77.18 ppm. HRMS (ESI): m / z calcd for C 19 H 10 BrClF3NO3S [M+H] + 503.9284, found 503.9288.

[0122]

[0123] Compound 3dd. PE:EA = 5:1, R f = 0.47, yellowish solid, mp: 198.6-200.3 °C. 1 HNMR (400 MHz, DMSO-d6) δ 8.42 (s, 1 H), 8.02 (d, J = 8.6 Hz, 1 H), 7.92 (d, J = 2.0 Hz, 1 H), 7.84 (s, 1 H), 7.42 - 7.31 (m, 2H), 7.27 (dt, J = 15.6, 8.3 Hz, 2H), 4.71 (d, J = 14.7 Hz, 1 H), 3.89 (s, 3H), 3.80 (d, J = 14.8 Hz, 1 H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 37.21, 75.35 (q, J = 29.6 Hz), 116.32, 118.34, 122.16, 123.92, 125.60, 125.62, 127.53 (q, J = 455.7 Hz), 128.79, 129.10, 131.31, 132.98, 134.25, 144.78, 152.47, 153.32, 153.85, 158.17, 158.64, 167.01 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.34, -77.18 ppm. HRMS (ESI): m / z calcd for C 20 H 13 ClF3NO4S [M+H] +456.0284, found 456.0285.

[0124]

[0125] Compound 3ea. PE:EA = 5:1, R f = 0.38, yellow solid, mp: 147.3-149.2 °C. 1 H NMR (400 MHz, DMSO-d6) δ 8.43 (s, 1H), 7.86-7.79 (m, 2H), 7.75 (s, 1H), 7.68-7.57 (m, 2H), 7.43 (d, J = 8.3 Hz, 1H), 7.33 (td, J = 7.6, 1.1 Hz, 1H), 7.16 (dd, J = 8.1, 1.7 Hz, 1H), 4.68 (d, J = 14.7 Hz, 1H), 3.77 (d, J = 14.7 Hz, 1H), 2.36 (s, 3H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 21.31, 37.12, 75.39 (q, J = 29.1 Hz), 116.35, 118.55, 121.92, 122.63, 123.12, 125.32, 125.49 (q, J = 289.1 Hz), 126.98, 129.80, 132.45, 133.48, 136.10, 145.64, 152.89, 153.84, 158.63, 164.48 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.27 ppm. HRMS (ESI): m / z calcd for C 20 H 14 F3NO3S [M-H] - 404.05682, found 404.05228.

[0126]

[0127] Compound 3ea. PE:EA = 5:1, R f = 0.52, white solid, mp: 154.6-156.9 °C. 1H NMR (400 MHz, DMSO-d6) δ 8.41 (s, 1H), 8.10 (d, J = 2.4 Hz, 1H), 7.85-7.80 (m, 2H), 7.76 (dd, J = 8.8, 2.4 Hz, 1H), 7.61 (s, 1H), 7.40 (d, J = 8.8 Hz, 1H), 7.15 (dd, J = 8.3, 1.7 Hz, 1H), 4.66 (d, J = 14.7 Hz, 1H), 3.76 (d, J = 14.7 Hz, 1H), 2.35 (s, 3H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 21.31, 37.00, 75.41 (q, J = 29.8 Hz), 116.93, 118.65, 120.39, 121.92, 122.64, 123.95, 124.51, 127.00, 131.80, 132.40, 135.77, 136.12, 144.44, 152.91, 158.11, 164.35 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.13 ppm. HRMS (ESI): m / z calcd for C 20 H 13 BrF3NO3S [M+H] + 483.9830, found 483.9834.

[0128]

[0129] Compound 3ed. PE: EA = 5: 1, R f = 0.4, yellowish solid, mp: 195.3-196.9 °C. 1 H NMR (400 MHz, DMSO-d6) δ 8.39 (s, 1H), 7.83 (d, J = 8.1 Hz, 1H), 7.75 (s, 1H), 7.64 (d, 2H), 7.29 (ddd, J = 24.4, 16.0, 8.1 Hz, 3H), 7.16 (d, J = 8.0 Hz, 1H), 4.68 (d, J = 14.6 Hz, 1H), 3.89 (s, 3H), 3.76 (d, J = 14.7 Hz, 1H), 2.36 (s, 3H) ppm. 13C NMR (101 MHz, DMSO-d6) δ 21.31, 37.13, 56.57, 75.36 (q, J = 29.1 Hz), 115.46, 119.09, 120.74, 121.93, 122.65, 123.26, 125.29, 125.48 (q, J = 289.0 Hz), 126.98, 132.46, 136.10, 143.17, 145.90, 146.61, 152.88, 158.35, 164.47 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.30 ppm. HRMS (ESI): m / z calcd for C 21 H 16 F3NO4S [M - H] - 434.06739, found 434.06253.

[0130]

[0131] Compound 3ef. PE:EA = 5: 1, R f = 0.35, white solid, mp: 198.1 -199.9 °C. 1 H NMR (400 MHz, DMSO-d6) δ 9.10 (s, 1 H), 8.40 (d, J = 8.4 Hz, 1 H), 8.22 (d, J = 9.1 Hz, 1 H), 8.04 (dd, J = 8.2, 1 H), 7.83 (s, 1 H), 7.78 (d, J = 8.2 Hz, 1 H), 7.73 (t, J = 7.7 Hz, 1 H), 7.65 - 7.56 (m, 3 H), 4.76 (d, J = 14.7 Hz, 1 H), 3.82 (d, J = 14.7 Hz, 1 H), 2.32 (s, 3 H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 21.31, 37.13, 56.57, 75.36 (q, J = 29.1 Hz), 115.46, 119.09, 120.74, 121.93, 122.65, 123.26, 125.29, 125.48 (q, J = 289.0 Hz), 126.98, 132.46, 136.10, 143.17, 145.90, 146.61, 152.88, 158.35, 164.47 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.30 ppm. HRMS (ESI): m / z calcd for C 24 H 16F3NO3S[M-H] - 454.07247, found 454.06749.

[0132]

[0133] Compound 3eg. PE:EA = 5:1, R f = 0.53, white solid, mp: 208.1-209.4 °C. 1 H NMR (400 MHz, DMSO-d6) δ 8.42 (s, 1H), 8.14 - 8.08 (m, 2H), 7.87 (s, 1H), 7.82 (d, J = 8.2 Hz, 1H), 7.61 (s, 1H), 7.14 (dd, J = 8.3, 1.6 Hz, 1H), 4.63 (d, J = 14.8 Hz, 1H), 3.78 (d, J = 14.8 Hz, 1H), 2.34 (s, 3H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 21.31, 36.96, 75.42 (q, J = 29.3 Hz), 110.30, 117.03, 121.28, 121.92, 122.66, 125.28, 125.32 (q, J = 289.1 Hz), 127.00, 131.52, 132.43, 136.12, 137.74, 144.44, 149.83, 152.92, 157.42, 164.27 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.08 ppm. HRMS (ESI): m / z calcd for C 20 H 12 Br2F3NO3S[M+H] + 561.8935, found 561.8939.

[0134]

[0135] Compound 3eg. PE:EA = 5:1, R f = 0.53, white solid, mp: 208.1-209.4 °C. 1 H NMR (400 MHz, DMSO-d6) δ 8.44 (s, 1H), 7.92 (d, J = 18.3 Hz, 2H), 7.85 - 7.72 (m, 2H), 7.60 (s, 1H), 7.12 (d, J = 8.3 Hz, 1H), 4.65 (d, J = 14.8 Hz, 1H), 3.79 (d, J = 14.8 Hz, 1H), 2.32 (s, 3H) ppm. 13CNMR(101MHz,DMSO-d6)δ21.25,36.92,75.46(q,J=29.3Hz),120.84,121.02,121.84,122.64,125.44,125.30( q, J=289.2Hz),126.94,127.93,129.03,132.31,132.42,136.07,144.42,148.30,152.94,157.26,164.25ppm. 19 F NMR(377MHz,DMSO-d6)δ-77.10ppm.HRMS(ESI):m / zcalcdfor C 20 H 12 Cl2F3NO3S[MH] - 471.97888, found 471.97346.

[0136]

[0137] Compound 3fa.PE:EA=5:1,R f =0.37, pale yellow solid, mp: 156.4-158.1℃. 1 H NMR(400MHz, DMSO-d6)δ8.46(s,1H),7.99(dd,J=8.9,5.4Hz,1H),7.87-7.76(m,2H),7.67(dd,J=9.8,2.6Hz,1H),7.59(ddd,J=8.7,7.4, 1.6Hz,1H),7.39(d,J=8.3Hz,1H),7.29(t,J=7.5Hz,1H),7.21(td,J=9.0,2.6Hz,1H),4.74(d,J=14.7Hz,1H),3.82(d,J=14.8Hz,1H)ppm. 13 CNMR(101MHz,DMSO-d6)δ37.36,75.35(q,J=29.1Hz),108.60,108.83,113.81,114.05,116.30,118.53,122.92,123.68,123.78 ,125.23,125.46(q,J=289.0Hz),129.77,131.33,133.42,145.88,153.20,153.32,153.86,158.66,160.28,162.68,167.52ppm. 19F NMR (377 MHz, DMSO-d6) δ -116.36, -77.37 ppm. HRMS (ESI): m / z calcd for C 19 H 11 F4NO3S[M+H] + 410.0474, found 410.0478.

[0138]

[0139] Compound 3ga. PE:EA = 5: 1, R f = 0.37, white solid, mp: 194.3-195.2 °C. 1 H NMR (400 MHz, DMSO-d6) δ 8.42 (s, 1H), 7.85-7.73 (m, 2H), 7.67-7.55 (m, 3H), 7.41 (d, J = 8.3 Hz, 1H), 7.31 (t, J = 7.5 Hz, 1H), 4.66 (d, J = 14.6 Hz, 1H), 3.74 (d, J = 14.7 Hz, 1H), 2.22 (s, 3H), 2.20 (s, 3H) ppm. 13 C NMR (101 MHz, DMSO-d6) δ 19.98, 19.99, 36.99, 75.38 (q, J = 29.2 Hz), 116.32, 118.53, 121.93, 122.77, 123.14, 125.28, 125.51 (q, J = 289.2 Hz), 129.77, 132.82, 133.42, 134.62, 135.32, 145.61, 151.27, 153.83, 158.58, 162.99 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.21 ppm. HRMS (ESI): m / z calcd for C 21 H 16 F3NO3S[M+H] + 420.0881, found 420.0885.

[0140]

[0141] Compound 3ha. PE:EA = 5: 1, R f = 0.42, orange yellow solid, mp: 165.4-166.8 °C. 1HNMR (400 MHz, DMSO-d6) δ 8.42 (s, 1H), 8.36-8.29 (m, 1H), 8.02 (d, J = 8.7 Hz, 1H), 7.98-7.89 (m, 1H), 7.84-7.71 (m, 3H), 7.61 (t, J = 7.3 Hz, 1H), 7.55-7.44 (m, 3H), 7.27 (t, J = 7.5 Hz, 1H), 4.85 (d, J = 14.7 Hz, 1H), 3.90 (d, J = 14.8 Hz, 1H) ppm. 13 CNMR (101 MHz, DMSO-d6) δ 36.84, 75.74 (q, J = 29.1 Hz), 116.24, 118.68, 119.92, 123.18, 123.94, 125.17, 125.57 (q, J = 289.0 Hz), 125.86, 126.48, 127.31, 127.90, 128.58, 129.66, 131.81, 132.07, 133.24, 145.00, 148.41, 153.93, 158.96, 163.81 ppm. 19 F NMR (377 MHz, DMSO-d6) δ -77.09 ppm. HRMS (ESI): m / z calcd for C 23 H 14 F3NO3S[M+H] + 442.0725, found 442.0729.

[0142] In combination Figure 27 The crystal data of compound 3ea is shown in Table 3.

[0143] Table 3 Crystal data of compound 3ea

[0144]

[0145] The synthesized compounds were subjected to activity detection, and the specific method was as follows:

[0146] Bacteriostatic experiment: according to the Chinese agricultural industry standard (NY / T 1156.2-2006), the mycelial growth rate method was used to determine the bactericidal or bacteriostatic activity of the compounds, and the specific process was as follows:

[0147] The obtained pathogenic fungi were activated and cultured for several days before the experiment. The code and name of the test fungi were as follows: A: Rhizoctonia solani, B: Fusarium moniliforme, C: Fusarium graminearum, D: Fusarium oxysporum, and E: Phytophthora parasitica.

[0148] 16.6 mg of the test sample was dissolved in 0.66 mL of DMSO, and then 0.1% Tween 80 was added to the water solution to prepare 500 μg / mL of the original drug. The test agent was taken in a sterile condition, and then was evenly poured into three culture dishes with a diameter of 9 cm. The above experiment was set without the agent to serve as a blank control, and each treatment was repeated three times. The commonly used pesticide triadimefon was used as a control group. The cultured pathogenic bacteria were cut into a bacterial cake along the edge of the colony under sterile conditions by using a puncher with a diameter of 5 mm, and the bacterial cake was inoculated in the center of the drug-containing plate by using an inoculator, and the mycelium was upward. The culture dish was covered with a dish cover, and was placed in a constant temperature incubator at 25 degrees Celsius for incubation. When the control colony diameter was expanded to more than 6 cm, the colony diameter was measured by using a cross method, and the average value was taken. The inhibition rate was calculated at the end of the culture, and the calculation formula was as follows:

[0149] Inhibition rate I = (D0-D t ) / D0*100%;

[0150] Wherein, D0 is the average diameter of the mycelium of the control plate, and D t is the average diameter of the mycelium of the sample plate. The inhibition effects of different compounds on six kinds of pathogenic bacteria are shown in Table 4.

[0151] Table 4: Inhibition effect data of each compound

[0152] Compound A B C D E 3ab 81±0 53±1 45±1 48±1 43±1 3ac 95±1 55±0 41±2 36±0 54±1 3ad 85±0 68±0 43±0 78±0 85±0 3ae 85±1 67±1 45±0 47±1 67±0 3af 79±2 73±0 62±1 39±0 40±1 3ba 97±0 65±2 33±0 46±0 68±1 3bb 75±1 63±0 48±1 50±1 69±0 3bc 79±0 50±1 62±1 46±0 55±2 3be 83±1 72±1 38±0 28±0 68±0 3bf 76±1 47±1 41±2 58±0 48±1 3ca 96±0 55±0 63±1 34±0 42±0 3cd 80±1 64±1 <10 82±0 60±1 3ce 67±2 37±2 25±1 <10 26±1 3cf 66±1 66±0 83±0 22±0 36±0 3da 78±0 53±1 61±1 19±0 68±0 3dc 76±1 47±2 18±0 43±0 69±1 3dd 64±1 48±1 44±1 74±1 43±1 3ea 98±0 89±0 65±1 80±0 71±0 3ec 87±1 90±1 56±1 45±1 39±1 3ed 99±0 53±0 43±2 69±0 67±2 3ef 76±1 51±1 52±0 41±0 63±1 3eg 75±1 57±0 78±0 52±1 62±0 3eh 67±1 48±1 41±1 34±0 25±2 3fa 93±1 87±0 44±0 57±0 73±1 3ga 57±0 56±0 23±0 <10 38±0 3ha 79±1 64±1 54±1 39±0 74±1 triazolinone 70±0 85±1 45±0 41±0 30±1

[0153] As can be seen from the data in Table 4, compared with the control group, the above compounds prepared in the application have better inhibition effects on one or more of the following: rhizoctonia solani, fusarium oxysporum, fusarium graminearum, fusarium oxysporum and phytophthora parasitica. The compounds in the application can exist in the form of pure products, or can be combined with one or more of the commercial fungicides to prepare a complex fungicide. According to the specific use requirements, the fungicide can be processed into emulsifiable concentrate, aqueous solution, powder, wettable powder, water dispersible granule or other suitable dosage forms.

[0154] As can be seen from the above, the active substructure of benzothiazole is introduced into the skeleton structure of the trifluoromethyl tertiary alcohol, a series of novel benzothiazole compounds are designed and synthesized, the inhibition effect on agricultural pathogenic bacteria is better, which is conducive to further development of high inhibition fungicide to meet the use requirements. In the preparation process of the application, no catalyst is used, the reaction conditions are mild, the process is simple, easy to implement, and is very suitable for large-scale production application, which provides a simple method support for further research on the derivatives.

[0155] It will be apparent to those skilled in the art that various modifications and variations can be made to the present application without departing from the spirit or scope of the application. Thus, it is intended that the present application cover modifications and variations of this application provided they come within the scope of the appended claims and their equivalents.

Claims

1. A process for the preparation of trifluoromethyl benzothiazole tertiary alcohol derivatives, characterized by, The method comprises the following steps: The structure of the trifluoromethyl-containing benzothiazole tertiary alcohol derivative is as follows: wherein R 1 , R 2 are each independently selected from hydrogen, C1-C3alkyl, C1-C3alkoxy or halogen; or R 1 , R 2 each independently with the substituted benzene ring constitutes a naphthalene ring; The trifluoromethyl-containing benzothiazole tertiary alcohol derivative shown in formula 3 is prepared from a compound of formula 1 and a compound of formula 2 by carbon-hydrogen bond functionalization, with sulfolane as a solvent; The synthesis route is as follows: The molar ratio of the compound of formula 1 to the compound of formula 2 is 1:

1. The temperature is 120-130 DEG C.

2. The production method according to claim 1, characterized by, The alkyl group is methyl, the alkoxy group is methoxy, and the halogen is fluorine, chlorine or bromine.

3. The preparation method according to claim 1, characterized in that, The trifluoromethyl-containing benzothiazole tertiary alcohol derivative is specifically the following compound:

4. The preparation method according to claim 1, characterized in that, The stirring reaction is carried out at a temperature of 120-130 DEG C for 4-13 hours.

5. The preparation method according to claim 4, characterized in that, The temperature is 120 DEG C, and the reaction time is 8-12 hours.

6. The method of claim 1, wherein, After the reaction is completed, the product can be purified by column chromatography.

7. The trifluoromethyl-containing benzothiazole tertiary alcohol derivative prepared by the method of claim 1 is applied to the preparation of an agricultural bacteriostatic agent.

8. Use according to claim 7, characterized in that, The agricultural bacteriostatic agent is used for inhibiting one or more of Rhizoctonia solani, Fusarium decemellum, Fusarium graminearum, Fusarium oxysporum and Phytophthora nicotianae.

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