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2,4-dichloro-6-(4-aminobenzotrifluoride)-1,3,5-triazine and preparation method and application thereof

A technology of trifluoromethylanilino and trifluoromethylaniline, applied to 2,4-dichloro-6-(4-trifluoromethylanilino)-1,3,5-triazine and its preparation and application fields to achieve the effect of great development potential

Inactive Publication Date: 2012-10-24
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] As a new compound, 2,4-dichloro-6-(4-trifluoromethylanilino)-1,3,5-triazine The preparation method and application as a bactericide have not been reported in the literature

Method used

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  • 2,4-dichloro-6-(4-aminobenzotrifluoride)-1,3,5-triazine and preparation method and application thereof
  • 2,4-dichloro-6-(4-aminobenzotrifluoride)-1,3,5-triazine and preparation method and application thereof
  • 2,4-dichloro-6-(4-aminobenzotrifluoride)-1,3,5-triazine and preparation method and application thereof

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Effect test

Embodiment 1

[0017] Synthesis of 2,4-dichloro-6-(4-trifluoromethylanilino)-1,3,5-triazine

[0018] Add 1.9 g (10 mmol) of cyanuric chloride to a 150 mL three-neck flask, add 30 mL of acetone, stir to dissolve, cool to 0 °C in an ice bath, slowly add 1.6 g (10 mmol) of p-trifluoromethylaniline dropwise 20 ml of acetone solution was added after 10 min, and the reaction was stirred at 0°C for 3 hours. After the completion of the reaction, the pH value of the reaction system was adjusted to 6 with 10% aqueous sodium carbonate solution, and a white solid was left to separate out. After suction filtration, the filter cake was recrystallized with ethanol and water, and after drying, 2.47 g of white solid was obtained. Yield: 80%, mp: 155~157℃, 1 H NMR (DMSO, 400 MHz) δ:7.73~7.75 (d, J=8.56 MHz, 2H, Ar H ), δ: 7.84~7.86 (d, J=8.68 MHz, 2H, Ar H ), δ: 11.47 (s, 1H, N H ); MS(ESI):309(M + ).

Embodiment 2

[0020] The bactericidal activity of the solvent was determined by the colony diameter in the growth rate method and the toxic medium culture method. On the aseptic operating table, first prepare a certain concentration of the solvent solution to be tested, then use a pipette gun to draw 1mL of the prepared solvent solution into a 7.5cm petri dish, use sterilized distilled water as a blank control, and then use sterilized Inject 9mL of melted PDA medium into a 10mL glass syringe, mix the liquid medicine and the medium evenly in the petri dish, and after cooling to room temperature, inoculate brown spot bacteria with a diameter of 5mm in the middle of the petri dish. Each treatment Do 3 repetitions, and finally put the inoculated petri dish into a constant temperature incubator at 28°C for about 30-40 hours. When the blank control is nearly full, use a ruler to measure the diameter of the colony. Measure 2 times, take the average value, and finally calculate the bacteriostatic r...

Embodiment 3

[0026] The bactericidal activity of the solvent was determined by the colony diameter in the growth rate method and the toxic medium culture method. On the aseptic operating table, first prepare a certain concentration of the solvent solution to be tested, then use a pipette gun to draw 1mL of the prepared solvent solution into a 7.5cm petri dish, use sterilized distilled water as a blank control, and then use sterilized Inject 9mL of melted PDA medium into a 10mL glass syringe, mix the liquid medicine and medium evenly in the petri dish, and after cooling to room temperature, inoculate cotton wilt bacteria with a diameter of 5mm in the middle of the petri dish. Repeat 3 times, and finally put the inoculated petri dish into a constant temperature incubator at 28°C and incubate for 40-60 hours. When the blank control is nearly full, measure the diameter of the colony with a ruler, and measure each petri dish with the cross method 2 times, take the average value, and finally cal...

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Abstract

The invention relates to 2,4-dichloro-6-(4-aminobenzotrifluoride)-1,3,5-triazine and a preparation method and application thereof. The structural formula is shown as follow. The preparation method includes adding cyanuric chloride and acetone solvent into a reactor, dropping aminobenzotrifluoride containing acetone solvent into the reactor when stirring, reacting for 1-3 hours at the temperature of -5-5 DEG C according to the mole ratio, 1:1-1.2 of the aminobenzotrifluoride to the cyanuric chloride, adding alkaline solution to adjust the pH (potential of hydrogen) value of the system to be 5-7 after reaction, precipitating and recrystallizing to obtain the 2,4-dichloro-6-(4-aminobenzotrifluoride)-1,3,5-triazine. The 2,4-dichloro-6-(4-aminobenzotrifluoride)-1,3,5-triazine can be applied to germicide for preventing mycosphaerella arachidicola of lawns and cotton wilt fusarium.

Description

technical field [0001] The invention relates to 2,4-dichloro-6-(4-trifluoromethylanilino)-1,3,5-triazine and its preparation method and application. Background technique [0002] Pesticides that are safe, efficient, economical, compatible with the environment, and easy to use meet the needs of agricultural production. Cyanuric chloride derivatives have a wide range of biological activities such as antibacterial, insecticidal, and herbicidal, and have great potential for the development of medicine and pesticides. The derivatives of cyanuric chloride have broad prospects for the development of green chemical pesticides because they are easily metabolized in the environment and have good environmental compatibility. Due to the expansion of the planting area of ​​vegetables in protected areas, the demand for fungicides is increasing year by year, especially fungicides that have antibacterial effects on fungi and bacteria are urgently needed in agricultural production. In the s...

Claims

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Application Information

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IPC IPC(8): C07D251/44A01N43/66A01P3/00
Inventor 巨修练李书托黄翔马静韩新才
Owner WUHAN INSTITUTE OF TECHNOLOGY
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