Method for preparing methylmercaptodiafenthiuron

A technology of methyl thiobutyl ether and methylation, which is applied in the direction of organic chemistry, can solve the problems of toxicity and high production cost, and achieve the effect of mild reaction conditions, high cost and high content

Active Publication Date: 2016-06-22
HAILIR PESTICIDES & CHEM GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The present invention reacts with diafenthiuron under alkaline conditions through a suitable and cheap methylating reagent, overcomes the high production cost and toxicity problems of using methyl iodide to prepare methylthio butafenthiuron, and is suitable for large-scale industrial production need

Method used

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  • Method for preparing methylmercaptodiafenthiuron
  • Method for preparing methylmercaptodiafenthiuron
  • Method for preparing methylmercaptodiafenthiuron

Examples

Experimental program
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Effect test

Embodiment 1

[0024]

[0025] In a 5L autoclave, 770g (2 moles) of diafenthiuron and 1.5L of methyl ethyl ketone were sequentially added, 134.4g (2.4 moles) of potassium hydroxide were added, 106g (2.1 moles) of methyl chloride was introduced, and after sealing, the temperature was raised to 70°C , React for 4 hours. After the reaction, the solvent was recovered under negative pressure, and 1L of water was added to the remaining materials, stirred at room temperature for 1 hour, filtered, and dried to obtain a white powder of methylthio diafenthiuron, 799.1g, content 97.6%, melting point 88-91°C. The rate is 98.0%.

Embodiment 2

[0027]

[0028] In a 5L autoclave, 770g (2 moles) of diafenthiuron and 1.8L of toluene were sequentially added, 268.8g (2.4 moles) of potassium tert-butoxide were added, and after stirring for 1 hour, 209g (2.2 moles) of methyl bromide was introduced. After sealing, The temperature was raised to 60°C and reacted for 4 hours. After the reaction, the solvent was recovered under negative pressure, and 1L of water was added to the remaining materials, stirred at room temperature for 1 hour, filtered, and dried to obtain a white powder of methionine, 792.6g, content 98.1%, melting point 89-91℃, The rate is 97.7%.

Embodiment 3

[0030]

[0031] Add diafenthiuron 770g (2 moles) and 1.5L N-methylpyrrolidone in a 3L reaction flask, add 129.6g (2.4 moles) of sodium methoxide and 270g (3 moles) of dimethyl carbonate, and heat to 180°C. React for 3 hours. After the reaction, the solvent was recovered under negative pressure, and 1.2L of water was added to the remaining materials, stirred at room temperature for 1 hour, filtered, and dried to obtain white powder methionine, 744.6g, content 97.1%, melting point 87-91°C, The yield was 90.8%.

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Abstract

The invention discloses a method for preparing methylmercaptodiafenthiuron. The method comprises the following reaction formula described in the specification, wherein in the formula, a methylation reagent is selected from methyl chloride, methyl bromide, methyl benzenesulfonate, methyl trifluoromethansulfonate, methyl p-toluenesulfonate, dimethyl carbonate, trimethyl phosphate, dimethyl sulfate, diazomethane, methyl trichloroethanimidate, and formaldehyde+formic acid; an alkali is selected from M2CO3, NCO3, MHCO3, MXR1, N(XR1)2, MH, NH2 or NO; M is selected from Li, Na or K; N is selected from Mg or Ca; X is selected from O or S; R1 is selected from H or C1-C6 alkyl. The compound shown in the reaction formula undergoes a reaction with the methylation reagent and the alkali in a proper solvent to prepare the methylmercaptodiafenthiuron. According to the method, the methylation reagent with low price is used, so the product cost is reduced; and the method is mild in reaction condition, simple, convenient and feasible in post-treatment method, economic and effective, and prone to industrialized production.

Description

Technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a method for preparing methylthio diafenthiuron. Background technique [0002] Methylthio butyl ether urea; chemical name: 1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)-2-methylisothiourea, which has a good killing effect Insect and acaricidal activity. Patent FR2465720 first reported the structure, preparation and biological activity of methionine diafenthiuron. The preparation method reported in the patent is as follows: DMF is used as a solvent, diafenthiuron and methyl iodide are reacted at 40°C, then kept at room temperature for 12 hours, then poured into water, potassium carbonate is adjusted to pH 12, extracted with dichloromethane, After dissolving, add hexane and cool to -50°C to crystallize. [0003] The reaction formula is as follows: [0004] [0005] In the above-mentioned preparation method, methyl iodide is used as a methylation reagent, and the production...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C335/32
Inventor 葛尧伦李建国
Owner HAILIR PESTICIDES & CHEM GRP
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