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Oxime ether derivatives of spirocyclic tetronic acid, the preparation thereof, and insecticidal, acaricidal, bactericidal and herbicidal usages thereof

A technology of spirotetronate oxime and its derivatives, which can be used in botany equipment and methods, chemicals for biological control, pesticides, etc., and can solve the problems that have not been reported in relevant literature

Inactive Publication Date: 2013-01-30
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although there are still many related studies on spirotetronic acid, a class of spirotetronic acid oxime ether derivatives involved in the present invention and its preparation have not been reported in relevant literature. Meanwhile, we have also studied weeding, insecticide, Acaricidal, fungicidal activity

Method used

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  • Oxime ether derivatives of spirocyclic tetronic acid, the preparation thereof, and insecticidal, acaricidal, bactericidal and herbicidal usages thereof
  • Oxime ether derivatives of spirocyclic tetronic acid, the preparation thereof, and insecticidal, acaricidal, bactericidal and herbicidal usages thereof
  • Oxime ether derivatives of spirocyclic tetronic acid, the preparation thereof, and insecticidal, acaricidal, bactericidal and herbicidal usages thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0022] Example 1 7-Hydroxy-6-(1-(methoxyimino)ethyl)-4-azaspiro[2.3]hexane-6-en-5-one

[0023] 1. Preparation of 5-acetyl Michaelis acid

[0024] In a 50mL round-bottomed flask, add 25mL of dichloromethane, then add 1mmol of acetic acid, add 1-1.5mmol of dehydrating agent DCC or EDCI, 0.1-1mmol of DMAP, and then add 1mmol of Michaelis acid, and control the reaction temperature at 0°C to room temperature. 8 to 17 hours, TLC follow-up monitoring, until the reaction stops. Then wash with hydrochloric acid, dry with anhydrous sodium sulfate or anhydrous magnesium sulfate, and directly make the raw material for the next step.

[0025] 2. Methyl 1-(3-carbonylbutyrylamino)cyclopropanecarboxylate

[0026] Add 25mL of ethyl acetate or acetonitrile into a 50mL round bottom flask, then add 1mmol of methyl 1-aminocyclopropanecarboxylate hydrochloride, stir for 5-10 minutes, add 1-1.1mmol of triethylamine, and then add 5- Acetyl Michaelis acid 1-1.5mmol, react at 50-100°C for 3-8 hours,...

example 2

[0031] Example 2 8-Hydroxy-7-(1-(methoxyimino)ethyl)-4-azaspiro[3.3]heptane-6-en-5-one

[0032] 1, 5-acetyl Michaelis acid preparation (referring to example 1.1)

[0033] 2. Methyl 1-(3-carbonylbutyrylamino)cyclobutylcarboxylate

[0034] Add 25mL of ethyl acetate or acetonitrile into a 50mL round bottom flask, then add 1mmol of methyl 1-aminocyclobutanecarboxylate hydrochloride, stir for 5-10 minutes, add 1-1.1mmol of triethylamine, and then add 5- Acyl Michaelis acid 1-1.5mmol, react at 50-100°C for 3-8 hours, and concentrate under reduced pressure. V (ethyl acetate): V (petroleum ether) = 1: 3 to 1: 0.5, and column chromatography was performed to obtain the product.

[0035] 3. 7-Acetyl-8-hydroxy-5-azaspiro[3.4]octane-7-en-6-one

[0036] Add methanol or ethanol to a 50mL round bottom flask, add 1mmol of methyl 1-(3-carbonylbutyrylamino)cyclobutyrate, add 1-1.5mmol of sodium methoxide or sodium ethoxide, and control the reaction temperature at 65-100°C. Concentrate under ...

example 3

[0039] Example 3 3-Hydroxy-2-(1-(methoxyimino)ethyl)-1-azaspiro[3.4]octane-3-en-2-one

[0040] 1, 5-acyl Michaelis acid preparation (referring to example 1.1)

[0041] 2. Methyl 1-(3-carbonylbutyrylamino)cyclopentylcarboxylate

[0042] Add 25mL of ethyl acetate or acetonitrile into a 50mL round bottom flask, then add 1mmol of 1-aminocyclopentylcarboxylic acid methyl ester hydrochloride, stir for 5-10 minutes, add 1~1.1mmol of triethylamine, and then add 5-acetyl 1 to 1.5 mmol of Metzler's acid, react at 50 to 100°C for 3 to 8 hours, and concentrate under reduced pressure. V (ethyl acetate): V (petroleum ether) = 1: 3 to 1: 0.5, and column chromatography was performed to obtain the product.

[0043] 3. 3-Acetyl-4-hydroxy-1-azaspiro[3.4]octane-3-en-2-one

[0044] Add methanol or ethanol to a 50mL round bottom flask, add 1mmol 1-(3-carbonylalkylamide) methyl cyclopentacarboxylate, add 1-1.5mmol of sodium methoxide or sodium ethoxide, and control the reaction temperature at 65-...

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Abstract

Oxime ether derivatives of spirocyclic tetronic acid, the preparation thereof, and insecticidal, acaricidal, bactericidal and herbicidal usages thereof. The present invention discloses spiro tetronic acid oxime ether derivatives with the following structure. The oxime ether derivatives of spirocyclic tetronic acid can be prepared by the following process of using 1-amino-or 2-amino cyclohydrocarbyl methyl formate as a raw material, and the oxime ether derivatives of spirocyclic tetronic acid are obtained after a Dieckmann cyclization reaction. These compounds are proved through biological activity test to have insecticidal, acaricidal, bactericidal and herbicidal activity, so can be used in pesticides as lead compounds.

Description

technical field [0001] The present invention relates to a class of spirocyclic quaternary acid oxime ether derivatives and a series of compounds prepared and used as insecticide, acaricide, fungicide and herbicide. Background technique [0002] Butanone lactam and its derivatives are a class of organic molecules that widely exist in nature. The parent is β-carbonyl five-membered ring lactam, and its scientific name is 4-hydroxyacetoacetam. The structural parent has two resonance structures, so It can also be considered as an acidic 1,3-diketone derivative. So far, a large number of natural product molecules containing butanolactam structural units have been discovered one after another. [0003] The novel structure of natural cyclic keto-enol makes it a synthetic precursor or intermediate of many important organic molecules, which has high chemical reactivity. Certain applications. [0004] Commercialized insecticides and acaricides Spirodiclofen, Spiromesifen and Spirotet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/96C07D221/20A01N43/42A01N43/38A01P13/00A01P7/02A01P7/04A01P3/00
Inventor 徐汉虹雷志伟姚光凯
Owner SOUTH CHINA AGRI UNIV
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