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A kind of method for preparing methylthio butafenthiuron

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 effects of mild reaction conditions, high cost and high synthesis yield

Active Publication Date: 2020-09-08
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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  • A kind of method for preparing methylthio butafenthiuron
  • A kind of method for preparing methylthio butafenthiuron
  • A kind of method for preparing methylthio butafenthiuron

Examples

Experimental program
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Effect test

Embodiment 1

[0024]

[0025] In a 5L autoclave, add 770g (2 moles) of diafenthiuron and 1.5L of methyl ethyl ketone in sequence, add 134.4g (2.4 moles) of potassium hydroxide, and feed 106g (2.1 moles) of methyl chloride. After sealing, heat up to 70°C , reacted for 4 hours. After the reaction, the solvent was recovered under negative pressure, 1L of water was added to the remaining material, stirred at room temperature for 1 hour, filtered, and dried to obtain white powder methylthiobuthiuron, 799.1g, content 97.6%, melting point 88-91°C, collected 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, and 268.8g (2.4 moles) of potassium tert-butoxide was added. After stirring for 1 hour, 209g (2.2 moles) of methyl bromide was introduced. After sealing, The temperature was raised to 60° C., and the reaction was carried out for 4 hours. After the reaction was completed, the solvent was recovered under negative pressure, 1L of water was added to the remaining material, stirred at room temperature for 1 hour, filtered, and dried to obtain white powder methylthio butafenthiuron, 792.6g, content 98.1%, melting point 89-91°C, collected The rate is 97.7%.

Embodiment 3

[0030]

[0031] Add 770g (2 moles) of diafenthiuron and 1.5L of N-methylpyrrolidone in sequence in a 3L reaction flask, add 129.6g (2.4 moles) of sodium methoxide, 270g (3 moles) of dimethyl carbonate, and raise the temperature to 180°C. React for 3 hours. After the reaction, the solvent was recovered under negative pressure, 1.2L of water was added to the remaining material, stirred at room temperature for 1 hour, filtered, and dried to obtain white powder methylthiobuthiuron, 744.6g, content 97.1%, melting point 87-91°C, The yield is 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 in particular relates to a method for preparing methylthio butafenthiuron. Background technique [0002] Methylthiobuthiuron; chemical name: 1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)-2-methylisothiourea, has good killing effect Insecticidal and acaricidal activity. Patent FR2465720 first reported the structure, preparation and biological activity of methylthiobuthiuron. The preparation method reported in this patent is: DMF is used as a solvent, diafenthiuron and methyl iodide are reacted at 40°C, and then kept at room temperature for 12 hours, and then poured into water, the pH value is adjusted to 12 with potassium carbonate, extracted with dichloromethane, and the After dissolving, add hexane and cool to -50°C to crystallize. [0003] The reaction formula is as follows: [0004] [0005] In the above preparation method, methyl iodide is used as a methylating reagent, and the ...

Claims

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Application Information

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