Pyraclostrobin crystal form and preparation method thereof

A technology of pyraclostrobin and crystal form, which is applied in the field of pesticide crystallization, can solve problems such as easy coalescence, low yield, and low melting point, and achieve the effects of simple operation, good repeatability, and good process yield

Active Publication Date: 2017-08-08
TIANJIN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Crystal form II is a metastable state, which can be easily converted into crystal form IV; crystal form IV is the more stable crystal form among the four crystal forms, with the highest melting point and the most widely used, but the method of conventional cooling crystallization to prepare crystal form IV yields It is not high, and the crystal form IV is needle-like crystals, which are easy to coalesce during the process and easy to nucleate secondary explosions. Solvent molecules and impurities are often contained in the product, which eventually leads to poor bulk density, fluidity and other performance of the crystal product. reduced, which brings certain difficulties to the preparation process

Method used

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  • Pyraclostrobin crystal form and preparation method thereof
  • Pyraclostrobin crystal form and preparation method thereof
  • Pyraclostrobin crystal form and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Weigh 120g of pyraclostrobin into a beaker, add 100mL of dichloromethane, stir and make it fully dissolved, evaporate the solvent at an evaporation rate of 5ml / h, and continue to distill 5ml without adding seeds after the solution reaches saturation. A total of 90 mL of solvent was evaporated at an evaporation rate of / h, filtered, washed, and the product was vacuum-dried at 35° C. for 7 hours to obtain 115 g of product with a yield of 96% and a purity of 99.9% by HPLC. The powder X-ray diffraction pattern of the product and figure 1 In agreement, the DSC spectrum is consistent with figure 2 unanimous.

Embodiment 2

[0034] Weigh 50g of pyraclostrobin into a beaker, add 60ml of dichloromethane and 40ml of cyclohexane, stir and dissolve it fully, evaporate at an evaporation rate of 30ml / h, the solution reaches saturation after evaporating for 30min, add 1g of Continue to evaporate 70ml of the solvent at an evaporation rate of 30ml / h, filter, wash, and vacuum-dry the product at 50°C for 8h to obtain 46.3g of the product with a yield of 93%. The purity was detected by HPLC 99.9%. The powder X-ray diffraction pattern of the product has characteristic peaks at 8.89, 9.05, 9.29, 11.75, 12.73, 14.72, 15.33, 17.80, 18.71, 22.16, 22.62, 25.64 degrees, and DSC shows that its melting point peak is 68.52°C.

Embodiment 3

[0036] Weigh 20g of pyraclostrobin into a beaker, add 50ml of dichloromethane and 50ml of n-hexane, stir and dissolve it fully, evaporate the solvent at an evaporation rate of 10ml / h, and when the solution reaches saturation Continue to evaporate the solvent at an evaporation rate of 10ml / h under the conditions to a total of 80mL, filter, wash, and vacuum-dry the product at 40°C for 8h to obtain 18.2g of product with a yield of 91% and a purity of 99.9% by HPLC. The powder X-ray diffraction pattern of the product has characteristic peaks at 8.87, 9.04, 9.27, 11.75, 12.72, 14.71, 15.32, 17.79, 18.69, 22.15, 22.61, 25.64 degrees, and DSC shows that its melting point peak is 69.73°C.

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Abstract

The invention relates to a pyraclostrobin crystal form and a preparation method thereof. The pyraclostrobin crystal form is characterized in that X-ray powder diffraction shows characteristic peaks when 2theta is 8.8+/-0.1 degrees, 9.0+/-0.1 degrees, 9.2+/-0.1 degrees, 11.8+/-0.1 degrees, 12.7+/-0.1 degrees, 14.7+/-0.1 degrees, 15.3+/-0.1 degrees, 17.8+/-0.1 degrees, 18.7+/-0.1 degrees, 22.2+/-0.1 degrees, 22.6+/-0.1 degrees, and 25.6+/-0.1 degrees. The preparation method comprises the following steps: dissolving a pyraclostrobin crude product in dichloromethane or a mixed solvent containing the dichloromethane; stirring and dissolving until a solution becomes clear; precipitating a crystal by evaporating or cooling and crystalizing; filtering crystal mush, washing and drying to obtain the pyraclostrobin crystal form. The method disclosed by the invention is easy to operate, the yield of a crystalizing process is 90 to 98 percent, the HPLC (High Performance Liquid Chromatography) detection purity of a product is 99.9 percent, and the product is a yellow crystal, has a flaky crystal habit, is smooth in surface and regular in edges, and has higher practical application value.

Description

technical field [0001] The invention belongs to the technical field of pesticide crystallization, and in particular relates to a crystal form of pyraclostrobin and a preparation method thereof. Background technique [0002] Pyraclostrobin, also known as pyraclostrobin, the chemical name is N-[[[1-(4-chlorophenyl)pyrazol-3-yl]oxy]-o-tolyl] -Methyl N-methoxycarbamate, the molecular formula is C 19 h 18 ClN 3 o 4 , the molecular weight is 387.82, and the chemical structural formula is: [0003] [0004] Pyraclostrobin is a methoxyacrylate fungicide with a pyrazole structure. It was discovered by BASF in 1993, registered and put into use in 2001. In 2009, its sales reached 735 million US dollars, becoming the second largest fungicide in the world after azoxystrobin. Pyraclostrobin is almost effective against the diseases caused by the four major fungal pathogens, and its mechanism of action is similar to other methoxyacrylate fungicides, mainly acting on the oxidation s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/22
CPCC07B2200/13C07D231/22
Inventor 龚俊波姜爽许辉唐剑峰侯宝红潘光民
Owner TIANJIN UNIV
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