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Slfonyl urea compounds and their production method and use

A technology for sulfonylureas and compounds is applied in the fields of sulfonylurea compounds and their preparation and use, and can solve problems such as damage to subsequent crops

Inactive Publication Date: 2005-01-26
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Most of the sulfonylurea compounds that have been reported are not only sensitive to weeds, but also sensitive to crops, but they all pose a hazard to subsequent crops. In addition, due to the long-term use of sulfonylurea herbicides, weeds will Grass develops certain resistance

Method used

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  • Slfonyl urea compounds and their production method and use
  • Slfonyl urea compounds and their production method and use
  • Slfonyl urea compounds and their production method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Example 1: Preparation of 2-amino-5-bromo-4-methylpyrimidine (VI).

[0074] Weigh 1.09g (about 0.01mol) of 2-amino-4-methylpyrimidine (III) into a 100ml round bottom flask, add 40ml of dichloromethane or acetic acid, and then add 0.38ml of liquid bromine (about 0.008mol) , the reaction solution was brownish red. The reaction temperature is 20-80 degrees, stirring for 0.5-2 hours. Remove the solvent and add lye to neutralize. CH 2 Cl 2 Extraction, the extract was washed with saturated NaCl. dry (anhydrous Na 2 SO 4 ). Column chromatography (40g silica gel H, 5% CH 3 OH / CH 2 Cl 2 elution) to obtain 0.7 g of white solid. The yield was 50%. TLC (2%CH 3 OH / CH 2 Cl 2 ) Rf = 0.11. [ 1 H] NMR (CD 3 Cl): δ8.19 (s, 1H, Pm), 5.00 (br.s, 2H, NH2), 2.41 (s, 3H, CH3). mp.170-175°C.

[0075] According to the method of Example 1, the compound of general structural formula (VI) of the present invention can be prepared. Example 2: Preparation of 2-amino-5-bromo-4-bro...

Embodiment 2

[0076] Weigh 1.09g (about 0.01mol) of 2-amino-4-methylpyrimidine (III) into a 100ml round bottom flask, add 40ml of dichloromethane or acetic acid, and then add 0.76ml of liquid bromine (about 0.015mol) , the reaction solution was brownish red. The reaction temperature remains between 20-80 degrees. After stirring for 0.5-2 hours, add lye for neutralization. CH 2 Cl 2 Extraction, the extract was washed with saturated NaCl. dry (anhydrous Na 2 SO 4 ). Column chromatography (40g silica gel H, 2% CH 3 OH / CH 2 Cl 2 elution) to obtain 1.4 g of white solid. Yield 52%[ 1 H] NMR (200MHz, CD 3 Cl): δ8.31(s, 1H, Pm), 5.09(br.s, 2H, NH2), 4.36(s, 2H, CH2).mp.184℃(decomposition)

Embodiment 3

[0077] Example 3: Preparation of 2-amino-5-bromo-4-methoxymethylpyrimidine (V).

[0078] Weigh 100mg (0.37mmol) of 2-amino-5-bromo-4-bromomethylpyrimidine (IV) and place it in a 50ml round bottom flask weighing 20ml of methanol, add 12mg of metal Na (about 0.52mmol), and reflux for 1- After 2 hours, the solid residue was washed with water after spin-drying, and separated by column chromatography (silica gel H15g, 3% CH 3 OH / CH 2 Cl 2 ) to obtain 60 mg of white solid. Yield 73%. TLC (3%CH 3 OH / CH 2 Cl 2 ) Rf = 0.3. [ 1 H] NMR (300MHz, CD 3 Cl): δ8.258 (s, 1H, Pm), 5.20 (br.s, 1H, NH2), 4.51 (s, 2H, CH2), 3.53 (s, 3H, CH3). mp.211-215°C.

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Abstract

The invention provides a slfonyl urea compounds and their production method and use, which are compounds having a structural formula I and their non-toxic salts, wherein R1 is nitro, halogen atom, CN, SCN, N[3], boron containing substituent, alkyl, alkoxy, alkoxycarbonyl, R2 and R3 are separately selected from H, CN, SCN, N[3], and halogen atom, R4 is H, halogen atom, CN, SCN, N[3], alkoxy, amido, alkyl, acylorxy, aryloxy, epoxy radical, X is a halogen atom.

Description

technical field [0001] The invention relates to a sulfonylurea compound, a preparation method and application thereof. Background technique [0002] There have been many reports of sulfonylurea compounds as herbicides. [0003] U.S. Patent No. 4,501,607 and U.S. Patent No. 4,419,121 disclose compounds of the following formula respectively: [0004] [0005] Chinese patent CN1038679C discloses the compound of the following formula: [0006] [0007] Most of the sulfonylurea compounds that have been reported are not only sensitive to weeds, but also sensitive to crops, but they all pose a hazard to subsequent crops. In addition, due to the long-term use of sulfonylurea herbicides, weeds will Grass develops some resistance. Therefore, designing and synthesizing herbicides with high efficiency, low toxicity, broad spectrum, high selectivity, low residue and low resistance is an urgent problem in the current pesticide research. Contents of the invention [0008] The i...

Claims

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Application Information

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IPC IPC(8): A01N47/36C07D239/69
Inventor 席真班树荣李正名崔东亮张弘罗丁牛聪伟陈文彬吴丽欢
Owner NANKAI UNIV