[(6-substituted-pyrimidine-4-oxy)phenyl]-3-methyl methoxyacrylate

A technology of methyl methoxyacrylate, radical oxygen, applied in the field of biochemistry

Active Publication Date: 2018-10-23
HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is also crop resistance to pesticides. For this reason, it is nec...

Method used

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  • [(6-substituted-pyrimidine-4-oxy)phenyl]-3-methyl methoxyacrylate
  • [(6-substituted-pyrimidine-4-oxy)phenyl]-3-methyl methoxyacrylate
  • [(6-substituted-pyrimidine-4-oxy)phenyl]-3-methyl methoxyacrylate

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Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1: the synthesis of compound 2

[0021] Compound 1 (304g, 2mmol), toluene (2L), glacial acetic acid (0.5L), and phosphorus pentoxide (500g) were added to the reactor, heated to reflux for 6 hours, after the reaction was complete, cooled to room temperature, and slowly added ice water , extracted three times with ethyl acetate, combined the organic phases, extracted with saturated brine, dried the organic phase over anhydrous sodium sulfate, concentrated to dryness under reduced pressure, and was directly used in the next reaction without purification. A small part was taken out for column chromatography to obtain compound 2 as white needle crystals. Melting point 48~50℃: 1H-NMR (400Hz, CDCl 3 ): 3.72 (s, 2H, CH 2 ), 7.08-7.32 (m, 4H, Ph-H).

Embodiment 2

[0022] Embodiment 2: the synthesis of compound 3

[0023] Take the raw materials of the previous step, add trimethyl orthoformate (265g, 2.5mmol), zinc chloride (13.6g, 0.1mol), raise the temperature to 110°C and continue the reaction for 4h, and cool down after the reaction. The reaction system was washed with ethyl acetate and water, the organic phase was separated and concentrated under reduced pressure to obtain compound 3. The product was directly used in the next reaction without further purification. Take out a small part of column chromatography to obtain compound 3 as a yellow-green solid with a melting point of 27-29°C: 1H-NMR (400Hz, CDCl 3 ), 4.13 (S, 3H, CH 3 ), 7.06-7.13 (m, 2H, Ph-H), 7.18-7.21 (m, 1H, CH), 7.53-7.56 (m, 2H, Ph-H).

Embodiment 3

[0024] Embodiment 3: the synthesis of compound 4 phenol sodium salt

[0025] Add methanol (2L) to the raw materials of the previous step, add sodium methoxide (130g, 2.4mmol) under ice-salt bath, continue to stir and react for 2h, and concentrate the reaction solution under reduced pressure for the next reaction directly. Take a small amount of the concentrate and add dilute hydrochloric acid to neutralize it to pH = 6, then extract it with ethyl acetate and water, concentrate the organic phase to dryness under reduced pressure, and purify it by column chromatography to obtain a colorless transparent oil Compound 4: 1H-NMR (400Hz, CDCl 3 ): 3.38 (s, 3H, OCH 3 ), 3.68(s, 3H, OCH 3 ), 4.95 (s, 1H, CH), 6.76-6.85 (m, 2H, Ph-H), 7.15-7.18 (m, 2H, Ph-H).

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PUM

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Abstract

The invention discloses [(6-substituted-pyrimidine-4-oxy)phenyl]-3-methyl methoxyacrylate having activity of inhibiting pathogenic bacteria on crops and relates to the technical filed of biochemistry.The compound has the structure general formula in the specification and has great activity in applications of inhibiting Fusarium oxysporum.f sp. cucumerinum, Cercospora arachidicola Hori, Macrophomakawatsukai, Rhizoctonia cerealis, Bipolaris maydis, Colletetrichum orbicalare, Fusarium fujikuroi and the like.

Description

technical field [0001] The invention relates to the technical field of biochemistry, and relates to [(6-substituted-pyrimidin-4-yloxy)phenyl]-3-methoxymethyl acrylate and a preparation method thereof. Background technique [0002] In the current agricultural development, disease prevention and control is a big problem that plagues farmers. If it is not prevented and controlled in time, the disease will develop rapidly in a short period of time, and the affected area will gradually expand. Seriously affect crop yields. With the widespread use of pesticides, the resistance of crop pathogens is getting stronger and stronger, and the development of high-efficiency and low-toxicity pesticides is an urgent problem. Therefore, the development of new pesticides can not only effectively delay the emergence of drug resistance in pathogenic populations, but also play a key role in the control of plant diseases. Methoxyacrylate fungicides are a new type of high-efficiency, broad-spec...

Claims

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Application Information

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IPC IPC(8): C07D239/52A01P3/00
CPCC07D239/52
Inventor 陶乐郭晓河李玉江王强董黎红常俊标余学军刘陆平
Owner HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI
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