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Preparation method and use of R-imazamox

A technology of imazamox and isopropanol, applied in the field of pesticides, can solve the problems of difficult characterization, low enantiomer preparation efficiency and the like, and achieve the effect of wide application range

Active Publication Date: 2018-01-19
ZHEJIANG UNIV
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Problems solved by technology

[0005] The purpose of the present invention is to solve the problems of low preparation efficiency and difficult characterization of imazamox enantiomers in the prior art, and provide a method for preparing imazamox high-efficiency, low-toxicity enantiomers, high-purity 100-milligram level standard products method and a more general enantiomeric characterization method

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  • Preparation method and use of R-imazamox
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  • Preparation method and use of R-imazamox

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Embodiment Construction

[0024] The present invention will be further elaborated and illustrated below in conjunction with the accompanying drawings and specific embodiments. The technical features of the various implementations in the present invention can be combined accordingly on the premise that there is no conflict with each other.

[0025] like figure 2 As shown, in this embodiment, the method for screening and preparing the high-efficiency and low-toxic imazethapyr enantiomer and its absolute configuration characterization includes the following steps:

[0026] 1) Dissolve Rac-imazethapyr in isopropanol to prepare 1000mg L -1 For the stock solution, use the semi-preparative chiral column OJ-H column to optimize the mobile phase, column temperature, flow rate and other conditions of high performance liquid chromatography, and balance the relationship between resolution and preparation time. Finally, n-hexane / isopropanol / trifluoroacetic acid (volume ratio 50 / 50 / 0.1) was used as the mobile pha...

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Abstract

The invention discloses a preparation method and use of R-imazamox. The preparation method comprises the steps of: S1: dissolving Rac-imazamox in isopropanol to prepare a stock solution, utilizing a semipreparative chiral column OJ-H column, and using high-performance liquid chromatography for chiral resolution to obtain two enantiomers; S2: subjecting the enantiomers to nitrogen blowing, then using n-hexane for redissolving, and conducting electronic circular dichroism test to obtain spectral feature graphs of the two; S3: conducting conformational search on the standard structures of R- andS- in imazamox, carrying out geometry optimization on the obtained preferred conformations, calculating circular dichroism spectra of the preferred conformations, and then superimposing the spectra ofthe conformations according to Boltzmann distribution numbers thereof so as to obtain calculation spectrograms of R-imazamox and S-imazamox; and S4: comparing the spectral feature graphs obtained byexperiments with the spectrograms obtained by calculation to confirm R-imazamox. The method provided by the invention can rapidly prepare high purity and hundred milligram grade high efficiency and low toxicity R-imazamox, and the enantiomer representation method is more universal.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a preparation method and application of R-imazethapyr. Background technique [0002] Imazamox was launched in 1997. Although it is the youngest product among imidazolinone herbicides, its sales volume and annual growth rate in recent years have outperformed all members of the group, becoming a veritable "double" champion. This product is mainly used in the control of weeds in sunflower, rapeseed, soybean, grain and rice fields. Based on the problem that imazethapyr does not have a long residual effect, imazethapyr has been gradually and effectively replaced, and this herbicide has been used in the Clearfield project. [0003] As one of the essential properties of nature, chirality exists widely in the macrocosm and microcosm. Important biological macromolecules such as proteins and nucleic acids all have chirality. Chiral imazethapyr (molecular configuration such as figur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A01N43/50A01P13/00
Inventor 谢婧倩刘维屏赵璐
Owner ZHEJIANG UNIV
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