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Triazolopyrimidinylsulfonamide compound, composition containing compound, and application of compound

An azolopyrimidine sulfonamide and compound technology, applied in the field of triazolopyrimidine sulfonamide compounds, can solve problems such as hindering amino acid synthesis, plant metabolism disorder, plant growth damage, etc., achieve high growth inhibitory activity, low preparation cost, The effect of fewer synthesis steps

Active Publication Date: 2016-03-16
HEILONGJIANG KAIAO TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Studies have found that triazolopyrimidine sulfonamide compounds can inhibit the activity of acetolactate synthase, a key enzyme in plant amino acid synthesis, hinder plant amino acid synthesis, cause plant metabolic disorders, and cause serious damage to plant growth or even death. Therefore, it can be used as a herbicide. The currently developed herbicides include penoxsulam, diflusulam, flumesulam, etc. The disadvantages are that the synthesis is difficult, the preparation method is complicated and the cost is high. High, structural modification and transformation to obtain triazolopyrimidine sulfonamide compounds with better herbicidal activity and crop safety, simpler synthesis and lower preparation cost, which is helpful to the development of chemical herbicides and reveals this type of herbicidal activity The structure-activity relationship of compounds is of great significance

Method used

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  • Triazolopyrimidinylsulfonamide compound, composition containing compound, and application of compound
  • Triazolopyrimidinylsulfonamide compound, composition containing compound, and application of compound
  • Triazolopyrimidinylsulfonamide compound, composition containing compound, and application of compound

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preparation example Construction

[0053] According to the second aspect of the present invention, there is also provided a preparation method of the triazolopyrimidine sulfonamide compound represented by formula (I), which comprises the following steps:

[0054] step 1) , Preparation of ethoxycarbonyl isothiocyanate: using ethyl acetate as a solvent, potassium thiocyanate and ethyl chloroformate are substituted to obtain a mixture of ethoxycarbonyl isothiocyanate and ethyl acetate;

[0055] Step (2) Preparation of N-(substituted pyrimidinyl)-N′-ethoxycarbonylthiourea: Add 2-amino-substituted pyrimidine to the mixture of ethoxycarbonyl isothiocyanate and ethyl acetate prepared in step (1) Or 4-amino substituted pyrimidine, and carry out a substitution reaction to obtain the product;

[0056] Step (3) Preparation of 2-amino-triazolo-substituted pyrimidine: using ethanol as a solvent, under alkaline conditions, hydroxylamine hydrochloride and the N-(substituted pyrimidinyl)-N′-ethoxycarbonylthiourea prepared in step ...

Embodiment 1

[0071] The triazolopyrimidine sulfonamide compound represented by formula (III) is prepared according to the method described in steps (1) to (7).

[0072]

[0073] step 1) , Preparation of ethoxycarbonyl isothiocyanate

[0074] In a 1000mL four-necked flask equipped with a stirrer, thermometer, reflux condenser, and dropping funnel, add 600mL ethyl acetate, add 97.2g (1mol) potassium thiocyanate under stirring, heat to 40℃, and add 106.3g dropwise (0.98mol) Ethyl chloroformate was added dropwise at a temperature lower than 45°C. After the addition, the temperature was controlled at 40°C and kept for 2h. When the reaction of ethyl chloroformate was completed, it was cooled to room temperature and filtered to remove the potassium salt. The mixture of ethoxycarbonyl isothiocyanate and ethyl acetate is ready for use.

[0075] Step (2) , Preparation of N-(4,6-Dimethoxypyrimidin-2-yl)-N′-ethoxycarbonylthiourea

[0076] Add 124.1g (0.8mol) of 2-amino-4,6-dimethoxypyrimidine to the reacti...

Embodiment 2

[0088] The preparation was carried out according to the method similar to that of Example 1, except that the 2-amino-4,6-dimethoxypyrimidine in step (2) was replaced with the same amount of 2,5-dimethoxy-4 -Aminopyrimidine to obtain the triazolopyrimidine sulfonamide compound represented by formula (IV) with a purity of 96.1%, and its hydrogen nuclear magnetic resonance spectrum as shown in figure 2 Shown.

[0089]

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Abstract

The invention discloses a triazolopyrimidinylsulfonamide compound having a structural formula shown in the description, a composition containing the compound, and an application of the compound. X1, X2, B1, B2, R1, R2, R3, R4 and R5 in the formula are as defined in the description. The triazolopyrimidinylsulfonamide compound has high growth inhibition activity on multiple broadleaf weeds and grassy weeds, has no obvious drug effects on corn, rice, cotton, wheat and other crops, also has the advantages of good crop safety, few synthesis steps, simple method and low preparation cost, and is suitable for large-scale industrial production.

Description

Technical field [0001] The invention belongs to the field of chemical herbicides, and specifically relates to a triazolopyrimidine sulfonamide compound, a composition containing the compound and its application. Background technique [0002] Studies have found that triazolopyrimidine sulfonamide compounds can inhibit the activity of acetolactate synthase, a key enzyme in plant amino acid synthesis, hinder plant amino acid synthesis, cause plant metabolism disorders, and cause serious damage to plant growth and even death. Therefore, it can be used as a herbicide. The herbicides that have been developed include penoxsulam, diflufentrazone, flumetsulam, etc. The disadvantages are the difficulty of synthesis, the complicated preparation method and the cost High, its structure is modified and modified to obtain the triazolopyrimidine sulfonamide compound with better herbicidal activity and crop safety, simpler synthesis and lower preparation cost, which is the development of the fiel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P13/00
CPCA01N43/90C07D487/04
Inventor 高金胜牛立中左殿发刘吉龙马轶超
Owner HEILONGJIANG KAIAO TECH DEV CO LTD
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