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(E)-methoxylimino methyl phenylacetate-containing aryl pyrazole compound and preparation method and application thereof

A technology of methoxyimino and methyl phenylacetate, applied in the field of agricultural fungicides, can solve problems such as serious environmental pollution

Inactive Publication Date: 2014-03-05
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of the pharmacophore requires the use of highly toxic methylation reagents, causing serious environmental pollution

Method used

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  • (E)-methoxylimino methyl phenylacetate-containing aryl pyrazole compound and preparation method and application thereof
  • (E)-methoxylimino methyl phenylacetate-containing aryl pyrazole compound and preparation method and application thereof
  • (E)-methoxylimino methyl phenylacetate-containing aryl pyrazole compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: Synthesis of (E)-2-methoxyimino-2-(4-methyl)methyl phenylacetate (compound IV)

[0031]

[0032] Add 1.78g (10mmol) of compound (V), 1.25g (15mmol) of methoxyamine hydrochloride and 50mL of methanol into a 100mL single-necked flask, and react under reflux for 4h. Cool to room temperature, adjust the pH to neutral with saturated sodium bicarbonate solution, evaporate the solvent under reduced pressure, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, filter, evaporate the solvent under reduced pressure to obtain a sticky substance, Separation and purification by column chromatography (filling with silica gel, petroleum ether / ethyl acetate) gave white solid IV with a yield of 70% and a melting point of 75-76°C. The NMR data ( 1 HNMR, 400MHz, internal standard TMS, solvent CDCl 3 ) as follows: δppm7.33(d, J=7.6Hz, 2H, Ar-H), 7.21(d, J=7.6 Hz, 2H, Ar-H), 4.05(s, 3H, OCH 3 ), 3.87 (s, 3H, OCH 3 ), 2.37 (s, 3H, CH ...

Embodiment 2

[0033] Embodiment 2: Synthesis of (E)-2-methoxyimino-2-(4-bromomethyl)methyl phenylacetate (compound III)

[0034]

[0035] Add 2.07g (10mmol) of compound (IV), 0.48g (2mmol) of BPO, 2.67g (15mmol) of NBS and 50mL of carbon tetrachloride into a 100mL single-necked flask, and react under reflux for 8h. Cool to room temperature, remove the solid by suction filtration, evaporate the solvent under reduced pressure to obtain a yellow viscous substance, separate and purify by column chromatography (filling with silica gel, petroleum ether / ethyl acetate) to obtain a white solid III with a yield of 85% and a melting point of 61 -62℃, NMR data ( 1 HNMR, 400MHz, internal standard TMS, solvent CDCl 3) as follows: δppm7.47-7.13 (m, 4H, Ar-H), 4.32 (s, 2H, CH 2 ), 4.04 (s, 3H, OCH 3 ), 3.85(s, 3H, OCH 3 ).

Embodiment 3

[0036] Example 3: Synthesis of (E)-2-methoxyimino-2-[4-(1-phenylpyrazole-3-oxymethyl)]phenylacetic acid methyl ester (compound 1-1)

[0037]

[0038] 0.48g (3.0mmol) of compound (II-1), 0.41g (3.0mmol) of potassium carbonate, 0.86g (3.0mmol) of compound (III) and 30mL of acetone were added to a 100mL single-necked flask, and the reaction was stirred under reflux for 4h. Cool to room temperature, filter off the white precipitate, evaporate the solvent under reduced pressure to obtain a viscous substance, separate and purify by column chromatography (filling with silica gel, petroleum ether / ethyl acetate), and obtain a white solid I-1 with a yield of 70%, melting point 75-76°C, NMR data ( 1 HNMR, 400MHz, internal standard TMS, solvent CDCl 3 ) as follows: δppm7.72(d, J=2.4Hz, 1H, CH), 7.61-7.20(m, 9H, Ar-H), 5.95(d, J=2.4Hz, 1H, CH), 5.28(s, 2H, CH 2 ), 4.02 (s, 3H, OCH 3 ), 3.93 (s, 3H, OCH 3 ).

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Abstract

The invention discloses an (E)-methoxylimino methyl phenylacetate-containing aryl pyrazole compound and a preparation method and application thereof. The preparation method comprises the following steps of reacting 2-(4-methyl phenyl)carbonyl methyl acetate V with methoxyamine hydrochloride to prepare a compound IV, reacting the compound IV with NBS (N-bromo-succinimide) and BPO (benzoyl peroxide) to synthesize a compound III, and reacting the compound III with 1-aryl-3-hydroxyl pyrazole II and an acid-binding agent to obtain the (E)-methoxylimino methyl phenylacetate-containing acryl pyrazole compound I. The invention also discloses the application of the compound in the preparation of bactericides.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides. It specifically relates to an arylpyrazole compound containing (E)-methoxyiminophenylacetic acid methyl ester, a preparation method, and the application of this type of compound in fungicides. technical background [0002] Population, food and environment are important issues for the sustainable development of society in the 21st century. To solve the food problem in agriculture, high-quality and high-yield must be achieved, and pesticides are an indispensable tool for preventing and controlling agricultural pests. However, with the long-term use of traditional chemical pesticides, the disadvantages such as excessive pesticide residues in agricultural products, increased human and animal poisoning incidents, increased resistance of diseases and insect pests, and destruction of ecological balance have emerged. Therefore, the development of new green pesticides with high efficiency, low tox...

Claims

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Application Information

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IPC IPC(8): C07D231/22A01P3/00
CPCA01N43/56C07D231/22
Inventor 李壹刘媛媛陈南青熊晓辉韦萍李杰胡来凤陈凯卜菁
Owner NANJING UNIV OF TECH