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Benzotriazole derivative, preparation method and application thereof as bactericide

A technology for benzotriazole and derivatives, applied in the field of benzotriazole derivatives and preparation, can solve the problems of affecting the final yield of target products, discount of bactericidal effect, etc., and achieve the effects of simple reaction and reduced content

Inactive Publication Date: 2020-04-07
NANCHANG HANGKONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This will inevitably affect the final yield of the target product; and isomers are also a kind of impurity, doping in the formulation of the final fungicide will also lead to a greatly reduced bactericidal effect

Method used

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  • Benzotriazole derivative, preparation method and application thereof as bactericide
  • Benzotriazole derivative, preparation method and application thereof as bactericide
  • Benzotriazole derivative, preparation method and application thereof as bactericide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation route of 2-(4-chloro-phenoxy-2-hydroxyhexyl)-4-dodecyloxy-4-dodecyloxy-1,2,3-benzotriazole is as follows Shown:

[0033]

[0034] (1) Preparation of 4-bromo-1,2,3-benzotriazole (1a)

[0035] In a three-necked flask, 1,2,3-benzotriazole (10 mmol) was dissolved in 100 ml of tetrahydrofuran, and liquid bromine (10.5 mmol) was slowly added thereto at room temperature, and then heated to 100° C. for 3 h. NaOH solution was added to quench the reaction, the organic phase was collected, and then purified by column, the eluent used was petroleum ether: dichloromethane=1:1 (n / n), 9.8 mmol of white solid was obtained, and the yield=98% .

[0036] 1H NMR (300MHz, CDCl 3 ): δ=10.2(s, 1H), 7.90(d, 1H,), 7.62(d, 1H), 7.29(m, 1H). HRMS(EI):C 6 h 4 BrN 3 [M + Na] + m / z theoretical value: 196.96, measured value: 196.01.

[0037] (2) Preparation of 4-dodecyloxy-1,2,3-benzotriazole (1b)

[0038] In a three-necked flask, 4-bromo-1,2,3-benzotriazole (1a) (10mmo...

Embodiment 2

[0050] Preparation of 2-(2-chloro-phenoxy-2-hydroxyhexyl)-4-tetradecyloxy-1,2,3-benzotriazole

[0051] Preparation method is with embodiment 1, and difference only is:

[0052] (1) Change dodecyl bromide into tetradecyl bromide;

[0053] (2) The ratio of catalyst Q is potassium tert-butoxide: potassium carbonate=1:2, n / n;

[0054] (3) Change p-chlorophenol to m-chlorophenol.

[0055] Finally a white solid was obtained, yield = 92%.

[0056] 1 H NMR (300MHz, CDCl 3 ):δ=7.68(d,1H),7.64(d,1H,),7.32(m,1H),7.31(m,1H),7.25(m,1H),7.03(d,1H),7.01(m ,1H),5.38(s,1H),4.06(m,2H),3.71(m, 2H),1.76-1.26(m,30H),2,44(m,1H),2.35(m,2H), 0.88 (m,3H).

[0057] HRMS(EI):C 32 h 48 o 3 N 3 Cl[M + Na] + m / z theoretical value: 558.20, measured value: 558.39.

Embodiment 3

[0059] Preparation of 2-(1-chloro-phenoxy-2-hydroxyoctyl)-4-hexadecyloxy-1,2,3-benzotriazole

[0060] Preparation method is with embodiment 1, and difference only is:

[0061] (4) Change dodecyl bromide into hexadecyl bromide;

[0062] (5) The ratio of catalyst Q is potassium tert-butoxide: potassium carbonate=1:3, n / n;

[0063] (6) Change p-chlorophenol to o-chlorophenol.

[0064] Finally a white solid was obtained, yield = 90%.

[0065] 1 H NMR (300MHz, CDCl 3 ):δ=7.65(d,1H),7.63(d,1H,),7.35(m,1H),7.30(m,1H),7.27(m,1H),7.08(d,1H),7.02(m ,1H),5.38(s,1H),4.06(m,2H),3.71(m, 2H),1.76-1.26(m,38H),2,44(m,1H),2.35(m,2H), 0.88 (m,3H).

[0066] HRMS(EI):C 36 h 56 o 3 N 3 Cl[M + Na] + m / z theoretical value: 613.40, measured value: 613.20.

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Abstract

The invention relates to a structure of a benzotriazole derivative. According to the structure, a long alkoxy chain is connected to a 4-position benzene ring of benzotriazole, and meanwhile, a large-volume chlorophenoxy structure is connected to a 2-position N atom. The invention also relates to a related preparation method of the benzotriazole derivative, an adopted catalyst Q is a mixture of potassium tert-butoxide and potassium carbonate, can inhibit the generation of isomeride while increasing the reaction conversion rate, thus effectively increasing the yield of the target product, and accordingly has the potential of industrial mass production. The invention also relates to application of the benzotriazole derivative as a bactericide, and the obtained bactericidal effect is equivalent to that of mainstream bactericides on the market at present. Therefore, the benzotriazole derivative has a huge commercialization prospect in the field of sterilization.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a benzotriazole derivative, a preparation method and an application as a fungicide. Background technique [0002] Triazole fungicides refer to fungicides containing triazole compounds in their chemical structure. Triazole compounds have a long history of use as fungicides. As early as the 1960s, Dutch inventors developed the first 1,2,4-triazole fungicide-verbendazim; almost at the same time, Germany Bayer Corporation and Belgian Janssen Corporation have also reported the bactericidal activity of triazole compounds containing substituents (Yang Huazheng, Today's Pesticides and Prospects, University Chemistry, 1992,7(5):1-6); in the 1970s, triazoles The compound shows its excellent bactericidal effect as a bactericide, which has attracted great attention from the scientific community and the agricultural circles. Alcohol (Lin Bingchen, New 1,2,4-triazole fungicides, ...

Claims

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Application Information

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IPC IPC(8): C07D249/18A01N43/647A01P1/00A01P3/00
CPCA01N43/647C07D249/18
Inventor 肖慧萍
Owner NANCHANG HANGKONG UNIVERSITY
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