High activity paichongding isomers and preparation method thereof

A technology of pifluridin and isomers, which is applied in the field of highly active pifluridin isomers and its preparation, and can solve problems such as drug resistance, lowering the quality of agricultural products, and polluting the environment

Inactive Publication Date: 2013-05-08
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because racemic pesticides contain low-efficiency or ineffective enantiomers, they will not only reduce the efficacy, pollute the environment and reduce the quality of agricultural products, but may also cause phytotoxicity or drug resistance

Method used

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  • High activity paichongding isomers and preparation method thereof
  • High activity paichongding isomers and preparation method thereof
  • High activity paichongding isomers and preparation method thereof

Examples

Experimental program
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preparation example Construction

[0129] The preparation method of the compound of the present invention

[0130] Compounds of formula A3 and / or formula A4 of the present invention can be prepared by the following methods, but the conditions of the method, such as the amount of reactants, solvents, bases, compounds used, reaction temperature, reaction time, etc. are not limited to the following Explanation. The compound of the present invention can also be conveniently prepared by optionally combining various synthetic methods described in the specification or known in the art. Such a combination can be easily performed by those skilled in the art to which the present invention belongs.

[0131] The preparation method of formula A3 compound and / or formula A4 compound

[0132] The preparation method of the compound of the formula A3 and / or the compound of the formula A4 of the present invention comprises the steps of: splitting the raw material of pichamidin containing the optical isomer shown in the formula A...

Embodiment 1

[0198] Example 1: Chiral HPLC separation to obtain four isomers of pichridam

[0199] Instruments and Conditions

[0200] University liquid chromatograph: Shimadzu, LC-20ATvp, SPD-M20Avp;

[0201] Chromatographic column: CHIRALPAK IC (Daicel, 30×250mm, 5μm);

[0202] Mobile phase: ethanol = 100

[0203] Flow rate: 1-20mL / min;

[0204]Injection volume: 2μL-2mL;

[0205] Detection wavelength: 325nm;

[0206] Column temperature: 20-35°C.

[0207] Experimental procedure

[0208] Prepare sample ethanol solution with pichridam, and prepare the sample solution by liquid chromatography according to the above conditions, collect the target components, take samples for analysis and record the chromatograms. The result is as figure 1 As shown in the figure, from left to right in the figure are the isomers A1, A2, A3 and A4 of piperacrid, and the retention times are 7.500, 8.790, 10.618 and 13.487 min respectively, achieving the baseline separation of the four isomers.

[0209] F...

Embodiment 2

[0214] Example 2: Separation by chiral HPLC to obtain the isomer A34 of piperidin

[0215] Instruments and Conditions

[0216] High performance liquid chromatography: Shimadzu, LC-20ATvp, SPD-M20Avp;

[0217] Chromatographic column: CHIRALPAK IC (Daicel, 30×250mm, 5μm);

[0218] Mobile phase: dichloromethane:methanol:diethylamine=50:50:0.1

[0219] Flow rate: 1-20mL / min;

[0220] Injection volume: 2μL-2mL;

[0221] Detection wavelength: 325nm;

[0222] Column temperature: 20-35°C.

[0223] Experimental procedure

[0224] Take the ethanol solution of the sample configuration of Pichamid, and carry out the liquid chromatography preparation of the university according to the above conditions, collect the target components, take samples and analyze and record the chromatograms, the results are as follows: figure 2 As shown in the figure, from left to right in the figure are the isomers A1, A2, A3 and A4 of pyracrid, the retention times are 3.722, 3.976, 4.666 and 5.624 min...

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Abstract

The present invention provides high activity paichongding isomers and a preparation method thereof. Specifically the present invention relates to high activity paichongding isomers and a preparation method thereof, wherein the isomers comprise a (11R,14S) paichongding isomer represented by a formula A3 and/or (11S,14R) paichongding isomer represented by a formula A4. The preparation method comprises: an enantiomer A34 preparation method, and an asymmetrical chiral synthesis method of the single configuration isomer compound represented by the formula A4. The isomers of the present invention provide higher activity compared to the existing paichongding industrial products. With the method, low efficacy isomers can be easily removed so as to significantly improve efficacy of pesticides. The formula A3 and the formula A4 are as the follows.

Description

technical field [0001] The invention relates to the field of pesticides, in particular to a highly active pichamidrim isomer and a preparation method thereof. Background technique [0002] Pichamid (compound of formula A) is a kind of insecticide with low toxicity and environment friendliness. At present, it has obtained the temporary registration certificate and production certificate of pesticide, and it will be launched in the domestic market soon. This type of compound has high activity against imidacloprid-resistant rice brown planthopper strains, and its activity is significantly higher than that of imidacloprid, and is expected to play an important role in the control of imidacloprid-resistant strains. [0003] [0004] Containing two chiral carbon atoms in the structure of piperacendr, it has the compound of formula A1 (ie (11R, 14R) pipechram), the compound of formula A2 (ie (11S, 14S) pipechram), the compound of formula A3 (ie (11S, 14R) piperacrid) and the com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A01N43/90A01P7/04
CPCY02P20/55
Inventor 徐晓勇钱旭红李超施小新朱瑞恒曾步兵李忠邵旭升须志平任莉萍
Owner EAST CHINA UNIV OF SCI & TECH
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