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Preparation method and application of N-nitro-N-(2,4,6-trifluorophenyl)benzenesulfonamide compounds

A technology of trifluorophenyl and benzenesulfonamide, which is applied in the field of pesticides, can solve the problems of not obvious bactericidal effect and achieve significant antibacterial activity and good growth regulation activity

Inactive Publication Date: 2019-10-08
INST OF AGRI QUALITY STANDARDS & TESTING TECH RES HUBEI ACADEMY OF AGRI SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Professor Xie Jiugao of Huazhong Agricultural University began to study N-nitro-2,4,6-trichloroaniline compounds in 1986. In 1992, he screened out the active double effect element-II (PGR). Crops have a strong physiological regulation effect. In 2012, our research group obtained N-nitro-2,4,6-trifluoroaniline by nitrating aromatic amines with a non-acid nitration system, and confirmed that this compound has better plant growth regulation on rice. activity (CN102311361), yet further antibacterial activity experiments show that the bactericidal effect of this compound is not obvious

Method used

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  • Preparation method and application of N-nitro-N-(2,4,6-trifluorophenyl)benzenesulfonamide compounds
  • Preparation method and application of N-nitro-N-(2,4,6-trifluorophenyl)benzenesulfonamide compounds
  • Preparation method and application of N-nitro-N-(2,4,6-trifluorophenyl)benzenesulfonamide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Compound I-1

[0020]

[0021] The synthetic preparation route is as follows:

[0022]

[0023] Add 0.588g (4.0mmol) of 2,4,6-trifluoroaniline into a 50mL three-neck round bottom flask, then add 10mL of chloroform and stir to dissolve, then add 0.64g of pyridine (8.0mmol), and stir for 0.5h , slowly add 0.704g (4.0mmol) 2,6-difluorobenzenesulfonyl chloride dropwise, and stir the reaction at room temperature for 3h. After the reaction is complete, pour 30mL of 5wt% hydrochloric acid into the reaction solution, stir at room temperature for 3min, and then separate the liquids. Take the lower organic layer, mix the sample with silica gel, and purify by column chromatography to obtain the intermediate;

[0024] Add 0.287g of the intermediate (1.0mmol) into a 50mL three-neck round-bottomed flask, then add 6mL of glacial acetic acid and stir to dissolve it, slowly add 3mL of fuming nitric acid dropwise, stir for 30min, then add dropwise 2mL of acetic anhydride, and stir...

Embodiment 2

[0029] By replacing 2,6-difluorobenzenesulfonyl chloride with benzenesulfonyl chloride and referring to the synthesis method of compound I-1, compound I-2 of the present invention can be prepared. The structural formula of compound I-2 is as follows:

[0030]

[0031] Compound 1-2 is a white solid, and its structural characterization data are as follows: 1 H NMR (600MHz, Chloroform-d), δ (ppm): 8.14 (d, J = 7.6Hz, 2H), 7.77 (t, J = 7.5Hz, 1H), 7.64 (t, J = 7.9Hz, 2H) ,6.91(t,J=7.9Hz,2H).

[0032] MS(-ESI)=286.01419(M-NO 2 ).calcd for C 12 h 7 f 3 N 2 o 4 S m / z=332.0786.

Embodiment 3

[0034] By replacing 2,6-difluorobenzenesulfonyl chloride with 4-methylbenzenesulfonyl chloride and referring to the synthesis method of compound I-1, compound I-3 of the present invention can be prepared. The structural formula of compound I-3 is as follows:

[0035]

[0036] Compound I-3 is a white solid, and its structural characterization data are as follows: 1 H NMR (600MHz, Chloroform-d), δ (ppm): 8.01 (d, J = 8.4Hz, 2H), 7.43 (d, J = 8.2Hz, 2H), 6.90 (t, J = 8.0Hz, 2H) ,2.50(s,3H).

[0037] MS(-ESI)=300.02240(M-NO 2 ), calcd.for C 13 h 9 f 3 N 2 o 4 S m / z=346.02351.

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Abstract

The invention discloses a preparation method of N-nitro-N-(2,4,6-trifluorophenyl)benzenesulfonamide compounds. The method comprises the following steps: dissolving 2,4,6-trifluoroaniline into trichloromethane, adding pyridine, performing a reaction under stirring, adding one substituted benzenesulfonyl chloride dropwise, performing stirring at a room temperature, adding 5 wt% hydrochloric acid, performing stirring at a room temperature, performing liquid separation, and performing purification to obtain an intermediate; dissolving the intermediate into glacial acetic acid, adding nitric acid dropwise, performing stirring, adding acetic anhydride dropwise, performing stirring, pouring the stirred material into ice water, performing stirring, performing suction filtration, and performing drying to obtain one compound I, wherein the compounds I have a chemical structure formula shown in the description, in the chemical structure general formula of the compounds I, R is a substituent groupon the benzene ring. The N-nitro-N-(2,4,6-trifluorophenyl)benzenesulfonamide compounds provided by the invention have better antibacterial activity and provide a basis for development of developmentof benzenesulfonamide compounds as effective components of a bacteriostatic agent in the later period.

Description

technical field [0001] The invention relates to the field of pesticides. More specifically, the present invention relates to a preparation method and application of N-nitro-N-(2,4,6-trifluorophenyl)benzenesulfonamide compounds. Background technique [0002] The research on N-nitro-substituted anilines (also known as substituted phenylnitroamines) compounds began in the United States in the 20th century. Barrington Cross et al. reported N-nitro-2,4,6-trisubstituted anilines in patent US3844762 The compound has the effect of inhibiting the elongation and promoting the stoutness of the stems of plants; Thomas et al. conducted a large number of activity experiments on the stems of gramineous crops, and found that N-nitro-substituted aniline compounds and their salts have effects on rice, wheat, corn, etc. The stems of the crops have a significant dwarfing and strengthening effect, and have an effect on increasing the yield of the fruit. Professor Xie Jiugao of Huazhong Agricul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/49C07C311/21C07C303/38C07C303/40A01N51/00A01P3/00
CPCA01N51/00C07C303/38C07C303/40C07C311/49C07C311/21
Inventor 姚晶晶岳霞丽周阳海蔡聪周衡
Owner INST OF AGRI QUALITY STANDARDS & TESTING TECH RES HUBEI ACADEMY OF AGRI SCI
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