CN-116354965-B - Process for preparing metabolite of triazolopyrimidine sulfonamide herbicide

Abstract

The invention discloses a preparation method of a metabolite of a triazolopyrimidine sulfonamide herbicide, which comprises the steps of reacting the triazolopyrimidine sulfonamide herbicide in an alkaline aqueous solution, adjusting the material after the reaction to be acidic by acid after the reaction, stirring, filtering, washing and drying to obtain the metabolite of the triazolopyrimidine sulfonamide herbicide. The invention provides a preparation method of partial metabolite of triazolopyrimidine sulfonamide herbicide, which has simple synthetic route steps and higher yield and purity of the product, and provides a material support for pesticide metabolite environment and toxicological tests in pesticide registration.

Inventors

• WU JINXIAN
• YAN JIANZHONG
• GU XIAOYU
• BU CHENGWEI
• WANG XINGYUAN
• ZHOU JUN
• BU KANGMING

Assignees

• 江苏瑞邦农化股份有限公司

Dates

Publication Date

20260505

Application Date

20221130

Claims (2)

1. 1. A method for preparing a metabolite of a triazolopyrimidine sulfonamide herbicide, which is characterized by comprising the following steps: ① The method comprises the steps of reacting a triazolopyrimidine sulfonamide herbicide shown in a formula (2) in an alkaline aqueous solution, dispersing the triazolopyrimidine sulfonamide herbicide shown in the formula (2) in water, then dropwise adding the alkaline aqueous solution at a temperature of 5-10 ℃ for reacting for 1-3 hours in the alkaline aqueous solution, wherein alkali in the alkaline aqueous solution is one or more of lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and the molar ratio of the triazolopyrimidine sulfonamide herbicide shown in the formula (2) to the alkali is 1:1-1:5; (2); ② After the reaction in step ① is finished, the reacted material is regulated to be acidic by acid, and the metabolic product of the triazolopyrimidine sulfonamide herbicide shown in the formula (1) is obtained through stirring, suction filtration, washing and drying; (1)。
2. 2. The method for preparing a metabolite of a triazolopyrimidine sulfonamide herbicide as claimed in claim 1, wherein in step ②, the acid used is one of hydrochloric acid, sulfuric acid and glacial acetic acid.

Description

Process for preparing metabolite of triazolopyrimidine sulfonamide herbicide Technical Field The invention relates to the technical field of organic synthesis, in particular to a preparation method of a metabolite of triazolopyrimidine sulfonamide herbicide, and specifically relates to a preparation method of 5-hydroxy-N-aryl-1, 2, 4-triazolopyrimidine-2 sulfonamide. Background The triazolopyrimidine sulfonamide herbicide has the characteristics of small dosage, good weeding effect and safety to aftercrop, has a good market share, and has been commercialized to cloransulam, diclosulam, florasulam and the like. According to the latest domestic pesticide registration policies, there is a need to provide pesticide metabolites for environmental and toxicological tests to evaluate risks to the environment, meals, etc., so preparing the pesticide metabolites is an important process to complete pesticide registration. The following formula (1) is a metabolite of triazolopyrimidine sulfonamide herbicides in plants and in the environment: (1); In the formula (1), R1 represents halogen or COOR, R in COOR represents hydrogen or C1-C4 lower alkyl, and X and Y represent halogen. However, no report exists on the preparation method of the compounds. Disclosure of Invention The technical problem to be solved by the invention is to provide a preparation method of 5-hydroxy-N-aryl-1, 2, 4-triazolopyrimidine-2 sulfonamide, which is a metabolite of triazolopyrimidine sulfonamide herbicide with simple steps and higher yield and purity. The technical scheme for realizing the aim of the invention is a preparation method of a metabolite of triazolopyrimidine sulfonamide herbicide, which comprises the following steps: ① Reacting a triazolopyrimidine sulfonamide herbicide represented by formula (2) in an alkaline aqueous solution; (2); In the formula (2), R1 represents halogen or COOR, R represents hydrogen or lower alkyl, X and Y represent halogen, and R2 represents C1-C4 lower alkyl. ② After the reaction in step ① is finished, the reacted material is regulated to be acidic by acid, and the metabolic product of the triazolopyrimidine sulfonamide herbicide shown in the formula (1) is obtained through stirring, suction filtration, washing and drying; (1); In the formula (1), R1 represents halogen or COOR, R in COOR represents hydrogen or C1-C4 lower alkyl, and X and Y represent halogen. In the step ①, the alkali is one or a combination of more than one of lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate. In the step ①, the triazolopyrimidine sulfonamide herbicide shown in the formula (2) is dispersed in water, and then an alkaline aqueous solution is added dropwise at 0-30 ℃. Preferably, in step ①, the triazolopyrimidine sulfonamide herbicide represented by formula (2) is dispersed in water, and then an alkaline aqueous solution is added dropwise at 5 to 10 ℃. In the step ①, the reaction temperature is 0 ℃ to 30 ℃. Preferably, in the step ①, the reaction temperature is 5 ℃ to 10 ℃. In the step ①, the molar ratio of the triazolopyrimidine sulfonamide herbicide shown in the formula (2) to the alkali is 1:1-1:5. In the step ①, the triazolopyrimidine sulfonamide herbicide shown in the formula (2) reacts in an alkaline aqueous solution for 1-3 hours In the step ②, the acid is one of hydrochloric acid, sulfuric acid and glacial acetic acid. The invention has the positive effects that the invention provides a preparation method of partial metabolic products of triazolopyrimidine sulfonamide herbicide, the triazolopyrimidine sulfonamide herbicide is reacted in alkaline aqueous solution, and dilute acid is used for acidification after the reaction is finished, so that the metabolic products, namely 5-hydroxy-N-aryl-1, 2, 4-triazolopyrimidine-2 sulfonamide, are obtained. The synthesis route has simple steps, and the yield and purity of the product are higher, thereby providing material support for the environment and toxicological test of the pesticide metabolite in pesticide registration. Drawings FIG. 1 is a mass spectrum of the product of example 1. FIG. 2 is an HPLC profile of the product of example 1. FIG. 3 is an HPLC profile of the product of example 6. Detailed Description The following presents a number of possible embodiments of the invention in order to provide a basic understanding of the invention and is not intended to identify key or critical elements of the invention or to delineate the scope of the invention. It is easy to understand that, according to the technical solution of the present invention, those skilled in the art may propose other implementations that can be replaced with each other without changing the true spirit of the present invention. Accordingly, the following detailed description is merely illustrative of the invention and should not be taken as an exhaustive or limiting example of the invention. The present invention provides a process for the preparation o