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Monosulfuron-methyl derivative and preparation method thereof, herbicide and weeding method

A technology of monosulfuron-methyl and its derivatives, which is applied in the field of monosulfuron-methyl derivatives and their preparation. It can solve the problems of not being able to use antifly, easy to block spray pipes, and poor water solubility of monosulfuron-methyl, and achieve excellent removal effect , Promote soil remediation, excellent herbicidal performance

Pending Publication Date: 2021-04-16
NANKAI UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Monosulfuron-methyl is a new type of sulfonylurea herbicide independently developed by our country. It has a good weeding effect, but monosulfuron-methyl is poor in water solubility, so it can only be prepared as wettable powder instead of water. Dosage or other liquid formulations, limiting its application
At the same time, because it can only be prepared as a wettable powder or its liquid formulation contains a large number of particles, it is easy to block the spray pipe when using the spraying agent for flying control, which in turn makes it impossible to use flying control.
Moreover, monosulfuron-methyl is not easy to decompose, and it has great environmental pollution. After use, there will be residues in the soil, which is not conducive to soil restoration and affects the subsequent planting of crops or other plants.

Method used

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  • Monosulfuron-methyl derivative and preparation method thereof, herbicide and weeding method
  • Monosulfuron-methyl derivative and preparation method thereof, herbicide and weeding method
  • Monosulfuron-methyl derivative and preparation method thereof, herbicide and weeding method

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preparation example Construction

[0045] The embodiment of the present invention also provides a preparation method of monosulfuron-methyl derivatives, comprising: reacting monosulfuron-methyl with a reaction material capable of forming a quaternary ammonium cation to form the monosulfuron-methyl derivatives.

[0046] Specifically, the reaction is carried out by mixing monosulfuron-methyl, an organic solvent, ammonia or an organic amine; wherein, the organic solvent is an aprotic solvent; for example, the organic solvent includes but is not limited to acetonitrile, acetone, 1,4-dioxane At least one of ring, dichloromethane, chloroform, 1,2-dichloroethane and tetrahydrofuran; the reaction temperature is 0-50°C, preferably 15-35°C, and the reaction time is 2-24 hours. Adoption of the above reaction conditions is beneficial to the progress of the reaction and to the improvement of the yield and purity of the monosulfuron-methyl derivatives.

[0047] Further, after the reaction is finished, the reaction mixture so...

Embodiment 1

[0057] The embodiment of the present invention provides a synthesis method of monosulfuron-methyl (N-[2'-(4-methyl)-pyrimidinyl]-2-nitrobenzenesulfonylurea) ammonium salt, comprising:

[0058] Weigh 0.05mol monosulfuron-methyl (16.85g) and 0.055mol (7.7g) of 25% ammonia water into 200mL of dichloromethane, stir at 25°C for 2 hours, after the reaction, add 200mL of water; The layer was precipitated to obtain a light yellow powder, and recrystallized with methanol to obtain a white needle-like crystal, which was the monosulfuron-methyl ammonium salt obtained in the embodiment of the present invention. The melting point is 175-176°C, and the yield: 96%.

[0059] The monosulfuron-methyl ammonium salt obtained by this embodiment is characterized (see Figure 2-Figure 4 ): Elemental analysis measured value is C:40.43%, H:4.69%, N:21.78%; Theoretical calculation is C:40.41%, H:4.70%, N:21.75%, all within the experimental error range; 'HNMR( DMSO-d6)δ values ​​were 2.29(s,3H, Pyrimi...

Embodiment 2

[0061] The embodiment of the present invention provides a synthesis method of monosulfuron-methyl (N-[2'-(4-methyl)-pyrimidinyl]-2-nitrobenzenesulfonylurea) methylamine salt, comprising:

[0062] Weigh 0.05mol monosulfuron-methyl (16.85g) and 8 milliliters of 40% methylammonia aqueous solution into 200 mL of dichloromethane, stir at room temperature for 2 hours, add 200 mL of water to dissolve; separate liquid, and precipitate the water layer to obtain a white solid , recrystallized with methanol to obtain white crystals, which is the monosulfuron-methyl salt of the present invention. The melting point is 173-175°C, and the yield: 95%.

[0063] To characterize it (see Figure 5 ), the characterization data are as follows: the elemental analysis measured values ​​are C: 42.39%, H: 4.28%, N: 22.92%; theoretical calculations are C: 42.39%, H: 4.38%, N: 22.81%, all within the experimental error range ; 1 HNMR(DMSO-d6)δ values ​​are 2.29(s,3H,pyrim-CH 3 ),2.33(s,3H,CH 3 NH 3 ...

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Abstract

The invention relates to the technical field of herbicides, in particular to a monosulfuron derivative and a preparation method thereof, a herbicide and a weeding method. The monosulfuron derivative comprises a compound represented by the following structural formula or an isomer thereof, and X represents a quaternary ammonium cation. The weeding composition not only has excellent weeding effect, but also has excellent water solubility, can be prepared into liquid preparations such as water aqua and the like, and can adopt flight control, so that the application of the weeding composition is expanded. Meanwhile, the monosulfuron derivative is relatively easy to degrade, is not easy to remain in soil, can provide fertility for the soil, and is beneficial to soil remediation.

Description

technical field [0001] The invention relates to the technical field of herbicides, in particular to monosulfuron-methyl derivatives and preparation methods thereof, herbicides and herbicide methods. Background technique [0002] Monosulfuron-methyl is a new type of sulfonylurea herbicide independently developed by our country. It has a good weeding effect, but monosulfuron-methyl is poor in water solubility, so it can only be prepared as wettable powder instead of water. Dosage or other liquid preparations limit its application. At the same time, because it can only be prepared as a wettable powder or its liquid formulation contains a large number of particles, it is easy to block the spray pipe when using the anti-flying spray agent, which in turn makes it impossible to use the anti-flying agent. Moreover, monosulfuron-methyl is not easy to decompose, and it has great environmental pollution. After use, there will be residues in the soil, which is not conducive to soil res...

Claims

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Application Information

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IPC IPC(8): C07D239/42A01N47/36A01P13/00
Inventor 童军郑占英李正名鲁森聂阳暴亚召孙洁
Owner NANKAI UNIV
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