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Methoxyl group displacement methyl acrylate compound bactericidal agent

A technology of methyl methoxy acrylate and methyl fluoromethoxy acrylate, which is applied in the application field of agricultural fungicides and can solve the problem of no side chain, no involvement, no side chain benzene ring nitro or alkoxycarbonyl and other problems, to achieve the effect of reasonable toxicity, high-efficiency bactericidal activity, and simple synthesis method

Inactive Publication Date: 2007-02-07
ZHEJIANG CHEM TECH GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the PCT / EP95 / 03683 patent application, it is disclosed that a group of fluoromethoxymethyl acrylate compounds with monofluoromethoxy replacing the original methoxy have fungicidal activity, but no compounds with heterocyclic side chains are involved. It also does not involve compounds with nitro or alkoxycarbonyl groups on the side chain benzene ring
At the same time, it does not involve compounds with only alkoxyiminomethyl substituents on the side chain benzene ring

Method used

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  • Methoxyl group displacement methyl acrylate compound bactericidal agent
  • Methoxyl group displacement methyl acrylate compound bactericidal agent
  • Methoxyl group displacement methyl acrylate compound bactericidal agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Compound 1

[0031] Synthesis of 2-[2-(5-cyano-2-methyl-phenyloxymethyl)-phenyl]-3-methoxymethyl acrylate

[0032] At room temperature, 1.33g (0.01 mole) of 2-methyl-5-cyanophenol was added to a three-necked flask containing 60ml of dry acetone in 150ml, then 2.76g (0.02 mole) of potassium carbonate was added, stirred at room temperature for 30 minutes, and then 2.85 g (0.01 mol) of methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate was added slowly. Then the reflux reaction was completed for 4 hours, filtered and concentrated to obtain a crude product. Column chromatography was performed using a mixture of ethyl acetate and petroleum ether (1:4) as the eluent to obtain 3.13 g of compound I as a white solid with a yield of 93%. The product was confirmed by nuclear magnetic resonance (1HNMR) and mass spectrometry (MS) analysis. The analysis results are as follows:

[0033] 1 HNMR: 2.324(3H, s), 3.732(3H, s), 3.885(3H, s), 5.012(2H, s), 6.917-6.920(1H, s), ...

Embodiment 2

[0036] Example 2 Compound 4

[0037] Synthesis of 3-[2-(2-methoxy-1-methoxycarbonyl-vinyl)-phenylmethoxy]-4-methyl-benzoic acid methyl ester

[0038] At room temperature, 3.32g (0.02 moles) of methyl 3-hydroxy-4-methylbenzoate was added to a 250ml three-necked flask filled with 100ml of dry acetone, then 5.52g (0.04 moles) of potassium carbonate was added, and stirred at room temperature for 30 minutes , and then slowly added 5.7 g (0.02 mol) of methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate. Then the reflux reaction was completed for 4 hours, filtered and concentrated to obtain a crude product. Column chromatography was performed using a mixture of ethyl acetate and petroleum ether (1:4) as the eluent to obtain 6.22 g of compound I as a pale yellow solid with a yield of 84%. Melting point: 97.2-101.6°C. The product was confirmed by nuclear magnetic resonance (1HNMR) and mass spectrometry (MS) analysis. The analysis results are as follows:

[0039] 1 HNMR: 2.316 (3H,...

Embodiment 3

[0040] Example 3 Compound 5

[0041] Synthesis of 2-{2-[4-(ethoxyiminomethyl)-phenyloxymethyl]-phenyl}-3-fluoromethoxymethyl acrylate

[0042] At room temperature, 4.95g (0.03 moles) of 4-(ethoxyimine-methyl)-phenol was added to a three-necked flask containing 100ml of dry acetone in 250ml, then 8.28g (0.06 moles) of potassium carbonate was added, stirred at room temperature for 30 minutes, and then slowly added 9.09 g (0.03 moles) of methyl 2-(2-(bromomethyl)phenyl)-3-fluoromethoxyacrylate. Then the reflux reaction was completed for 4 hours, filtered and concentrated to obtain a crude product. Column chromatography was performed using a mixture of ethyl acetate and petroleum ether (1:4) as the eluent to obtain 8.94 g of compound I as a white solid with a yield of 77%. Melting point: 74.1-76.1°C. The product was confirmed by nuclear magnetic resonance (1HNMR) and mass spectrometry (MS) analysis. The analysis results are as follows:

[0043] 1 HNMR: 1.307 (3H, t), 3.823 (...

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Abstract

The invention relates to a group of methoxyl methyl acrylate compounds having a formula (I), wherein X=F or H, Q=N or CH; R1, R2, R3, R4=H, NO2, CN, Cl, C1-C9 alkyl or unsaturated hydrocarbons, C1-C6 alkoxy imine methyl, or C1-C6 alkoxy carbonyl. The invention also discloses the process for preparing the compounds and the use of the compounds in making agricultural bactericides.

Description

technical field [0001] The present invention mainly relates to a new methyl methoxyacrylate compound, a preparation method of the compound, and an application of the compound as an agricultural fungicide. Background technique [0002] Methyl methoxyacrylate fungicides are high-efficiency agricultural fungicides derived from natural compounds through structural modification. They are characterized by wide sterilization, low toxicity to other organisms, and good environmental compatibility. Many large pesticide companies in the world have conducted research in this area and discovered several methyl methoxyacrylate compounds with good market prospects. The market share of this type of fungicide is increasing, and it may replace triazole fungicides to become the largest variety of agricultural fungicides. [0003] Some methyl methoxyacrylate compounds are disclosed in US 4,914,128 patent application, and it is disclosed that the compounds have fungicid...

Claims

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Application Information

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IPC IPC(8): A01N43/40
Inventor 孔小林胡伟群郑昀红张晓铭朱卫纲窦花妮陈定花邢家华
Owner ZHEJIANG CHEM TECH GRP CO LTD
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