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High potent herbicide R-napropamide and preparation method thereof

A technology of napropamide and herbicide, which is applied in the field of high-efficiency herbicide R-napropamide and its preparation, which can solve the problems of reporting the high-efficiency herbicide of napropamide, and achieve the effect of shortening the enantiomeric time

Inactive Publication Date: 2018-06-08
RES INST OF ZHEJIANG UNIV TAIZHOU
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is still no literature report available for large-scale resolution of an effective method for the preparation of napropamide enantiomers. In addition, there is no report on the herbicidally efficient body of napropamide

Method used

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  • High potent herbicide R-napropamide and preparation method thereof
  • High potent herbicide R-napropamide and preparation method thereof
  • High potent herbicide R-napropamide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Dissolve racemic Rac-Napropamide in ethanol to prepare 1000mg L -1 stock solution, and then carry out chiral resolution to it by HPLC high-performance liquid chromatography, chromatographic column model Chiralcel OJ-H (10mm × 250mm), mobile phase n-hexane / IPA=85 / 15, flow rate 5ml min -1 , temperature 40°C. Prepare the resolution chromatogram as figure 2 As shown, there are two chromatographic peaks in the figure, indicating that two types of enantiomers pk1 and pk2 were separated.

[0039] The prepared pk1 and pk2 were subjected to electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) tests to obtain spectral characteristic maps of the two. Obtain the structure of R-napropamide from The PubChem Project, use computeVOA to perform conformation search, use guassian 09 to optimize the geometry of the obtained dominant conformation, calculate the circular dichroism spectrum of these dominant conformations, and then divide the spectra of each conform...

Embodiment 2

[0041] Using the R-napropamide obtained in Example 1, the target barnyardgrass was selected for herbicidal activity experiments. The experimental results showed that the R-herbicidal activity was higher than that of the S- and Rac-configurations. (table 3)

[0042] Table 3 Effect of napropamide on barnyardgrass root indicators

[0043]

[0044]

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Abstract

The invention discloses a high potent herbicide R-napropamide and a preparation method thereof. The method comprises the following steps: S1, dissolving Rac-napropamide into ethyl alcohol to obtain astock solution; and performing chiral resolution on the stock solution through high performance liquid chromatography to obtain two types of enantiomers; S2, correspondingly performing electronic circular dichroism and vibration circular dichroism test on the prepared two types of enantiomers so as to obtain spectrograms of the two types of enantiomers; S3, performing conformation search on standard structures of R-napropamide and S-napropamide; performing geometry optimization on the obtained preferential conformations; calculating circular dichroism spectra of the preferential conformations;and overlapping the spectra of each conformation based on related Boltzmann distribution number to obtain calculation spectra of R-napropamide and S-napropamide; and S4, comparing the spectrograms ofthe two types of enantiomers with the calculating map obtained in step S3, and determining the R-napropamide. According to the method, the time of separating enantiomers of napropamide is decreased,and high potent napropamide can be quickly massively prepared.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a high-efficiency herbicide R-napropamide and a preparation method thereof. Background technique [0002] Herbicides are widely used in agriculture and account for the majority of agrochemicals used today. Enantiomers of chiral herbicides usually share the same physicochemical properties but often exhibit different biochemical effects. The "active body" may show a higher herbicidal effect, while other enantiomers may not, or even have the opposite effect. Using a single enantiomer for weed control can reduce the amount of herbicide used and reduce the total amount of chemical pollutants released into the environment. [0003] Napropamide, chemical name N,N-diethyl-2-(α-naphthyloxy)propionamide, has a chiral carbon in the molecule, so there is a pair of enantiomers (such as figure 1 ). It is an amide selective pre-emergence soil treatment herbicide for controlling annual ...

Claims

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Application Information

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IPC IPC(8): C07C231/20C07C235/20A01N37/36A01P13/00
CPCA01N37/36C07B2200/07C07C231/20C07C235/20
Inventor 谢婧倩丁锦建刘维屏赵璐张红陶
Owner RES INST OF ZHEJIANG UNIV TAIZHOU
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