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Triazolopyrimidine sulfonamide compound, composition containing the same and application thereof

The technology of an azolopyrimidine sulfonamide compound, which is applied in the field of triazolopyrimidine sulfonamide compounds, can solve problems such as hindering amino acid synthesis, plant metabolic disorder, and plant growth damage, achieving high growth inhibitory activity, low preparation cost, The effect of fewer synthesis steps

Active Publication Date: 2017-11-07
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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  • Triazolopyrimidine sulfonamide compound, composition containing the same and application thereof
  • Triazolopyrimidine sulfonamide compound, composition containing the same and application thereof
  • Triazolopyrimidine sulfonamide compound, composition containing the same and application thereof

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preparation example Construction

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

[0054] step 1) , the preparation of ethoxycarbonyl isothiocyanate: using ethyl acetate as a solvent, potassium thiocyanate and ethyl chloroformate are subjected to a substitution reaction to obtain a mixed solution of ethoxycarbonyl isothiocyanate and ethyl acetate;

[0055] step (2) , the preparation of N-(substituted pyrimidinyl)-N'-ethoxycarbonylthiourea: add 2-amino substituted pyrimidine to the mixed solution of ethoxycarbonyl isothiocyanate and ethyl acetate that step (1) makes Or 4-amino substitution pyrimidine, carry out substitution reaction, obtain described product;

[0056] step (3), the preparation of 2-amino-triazole and substituted pyrimidine: take ethanol as solvent, under basic conditions, hydroxylamine hydrochloride and N-(substituted pyrimi...

Embodiment 1

[0071] The triazolopyrimidinesulfonamide compound represented by the 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, a thermometer, a reflux condenser, and a dropping funnel, add 600mL of ethyl acetate, add 97.2g (1mol) of potassium thiocyanate while stirring, raise the temperature to 40°C, and add 106.3g of (0.98mol) ethyl chloroformate, add dropwise at a controlled temperature lower than 45°C. After the dropwise addition, control the temperature at 40°C and keep it warm for 2h. After the reaction of ethyl chloroformate is complete, drop it to room temperature, remove the potassium salt by filtration, and obtain The mixture of ethoxycarbonyl isothiocyanate and ethyl acetate is ready for use.

[0075] step (2) , the preparation of N-(4,6-dimethoxypyrimidin-2-yl)-N'-ethoxycarbonylthiourea

[0076] Add ...

Embodiment 2

[0088] Prepare according to a method similar to Example 1, the only difference is that the 2-amino-4,6-dimethoxypyrimidine in step (2) is replaced by an equivalent amount of 2,5-dimethoxy-4 -Aminopyrimidine, obtain the triazolopyrimidine sulfonamide compound shown in formula (Ⅳ), purity 96.1%, its H NMR spectrum is as follows 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, in particular to a triazolopyrimidine sulfonamide compound, a composition containing the compound and an application thereof. 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 the amino acid synthesis of plants, 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...

Claims

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Application Information

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