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Macrolide benzoate compound, intermediate compound thereof, preparation method of the intermediate compound, and application of the macrolide benzoate compound

A technology of benzoate compounds and macrolides, applied in the field of pesticides, can solve the problems of low activity, utilization, waste and the like, and achieve the effects of high activity, simple preparation method and wide application.

Inactive Publication Date: 2017-02-01
河北艾林化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the Abamectin B produced in the prior art 2 The activity is low, it cannot be used in agriculture or other industries, and the problem of waste is generated. The present invention provides a kind of abamectin B with high activity that can be applied to agricultural production. 2 Benzoate compounds

Method used

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  • Macrolide benzoate compound, intermediate compound thereof, preparation method of the intermediate compound, and application of the macrolide benzoate compound
  • Macrolide benzoate compound, intermediate compound thereof, preparation method of the intermediate compound, and application of the macrolide benzoate compound
  • Macrolide benzoate compound, intermediate compound thereof, preparation method of the intermediate compound, and application of the macrolide benzoate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: When R is methyl, the preparation of compound II

[0044] (1) 5-position hydroxyl protection: take compound a: Abamectin B 2b Dissolve in dichloroethane solvent, and cool the material liquid to -10~-25°C, then keep it warm for 1-2h. After the heat preservation is over, add the prepared allyl chloroformate and tetramethylethylenediamine solution dropwise at the same time to react; after the reaction is terminated, compound b: 5-protected avermectin B 2b Compound, compound a: allyl chloroformate: the molar ratio of tetramethylethylenediamine is 1:3~4:1~5;

[0045] (2) Oxidation of hydroxyl group at the 4″ position: Add compound b obtained in step (1), and then add tetramethylethylenediamine and dimethyl sulfoxide to mix well, and cool down to -13~-16°C, then dropwise add Phenyl phosphate dichloride, and keep the liquid temperature at -18°C for reaction; after the reaction is terminated, compound c is obtained after extraction: 5-O-allyl-4"-carbonyl-abamect...

Embodiment 2

[0049] Embodiment 2: When R is ethyl, the preparation of compound II

[0050] (1) 5-position hydroxyl protection: take the avermectin B shown in formula a 2a Dissolve in dichloroethane solvent, and cool the feed solution to -18°C, then keep it warm for 1.5h. After the heat preservation is over, add the prepared allyl chloroformate and the ethane solution of tetramethylethylenediamine dropwise at the same time to react; after the reaction is terminated, the abamectin B with the 5-position protection shown in formula b is obtained 2a compound;

[0051] (2) Oxidation of hydroxyl group at the 4″ position: Add compound b obtained in step (1), and then add tetramethylethylenediamine and dimethyl sulfoxide to mix well, and cool down to -13~-16°C, then dropwise add Phenyl phosphate dichloride, and keep the liquid temperature at -18°C for reaction; after the reaction is terminated, the 5-O-formyl-4"-carbonyl-abamectin shown in formula c is obtained after extraction B 2a ;

[0052]...

experiment example 3

[0055] Experimental Example 3: Preparation of Compound I

[0056] Take compound II prepared in Example 1 or 2, add benzoic acid with a molar ratio of 1:1.05 to compound II, and conduct a salt-forming reaction at a temperature of 75°C and a pressure of -0.09Mpa to obtain compound I.

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Abstract

The invention provides a macrolide benzoate compound, an intermediate compound thereof, a preparation method of the intermediate compound, and an application of the macrolide benzoate compound. The macrolide benzoate compound has high activity and can be applied in agricultural production. The invention also provides the intermediate compound of the macrolide benzoate compound and the preparation method of the intermediate compound. The preparation method is simple and is suitable for industrial production. The invention also provides an application of the macrolide benzoate compound for preparation of pesticides, especially, preparation of pesticides for preventing and treating plutella xylostella on brassicaceous vegetable or cucumber root knot nematode.

Description

technical field [0001] The invention relates to the field of pesticides, in particular to a macrolide benzoate compound, an intermediate compound, a preparation method and an application thereof. Background technique [0002] my country is a large agricultural country, with an area of ​​about 400 million hectares of crops. However, due to the occurrence of crop diseases, insect pests and weeds all year round, about 800,000 tons of pesticides need to be produced and used every year, and pesticides have become an indispensable factor of production in agricultural production. However, the long-term irrational use of chemical pesticides has also brought many disadvantages such as environmental pollution, direct toxicity to non-target organisms, and negative effects such as plant resistance. Therefore, research on new pesticides with good environmental compatibility, safety, low residue and economy will become the development trend in the future. [0003] Abamectin is a new typ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08C07H1/00A01N43/90A01P5/00A01P7/04
CPCC07H17/08A01N43/90C07H1/00
Inventor 孟水强杨中军
Owner 河北艾林化工科技有限公司
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