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Substituted phenyl ketone compounds with ether structure, and preparation method and application thereof

A compound, phenyl ketone technology, applied in the field of phenyl ketone compounds, can solve the problems of undisclosed compounds, activity of undisclosed compounds, etc.

Inactive Publication Date: 2018-07-10
ZHEJIANG RES INST OF CHEM IND CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The prior art does not disclose the compounds described in the present application, nor does it disclose the herbicidal activity of the compounds described in the present application

Method used

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  • Substituted phenyl ketone compounds with ether structure, and preparation method and application thereof
  • Substituted phenyl ketone compounds with ether structure, and preparation method and application thereof
  • Substituted phenyl ketone compounds with ether structure, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0166] Example 1, 2-methyl-4-thiamphenyl-3-(2-(p-tolyloxy)ethoxy)benzoic acid 1,3-dimethyl-1-H-pyrazole-5-ester Synthesis of (III-1)

[0167] 0.20 moles of 2-methyl-4-thiamphenyl-3-(2-(p-tolyloxy)ethoxy)benzoyl chloride (I-1) was dissolved in tetrahydrofuran, and it was added dropwise to 1, In a mixed solution of 0.20 moles of 3-dimethyl-1-H-5-hydroxypyrazole (II-1), 0.24 moles of triethylamine and tetrahydrofuran, continue to stir for 2 hours, filter, concentrate and remove the mother liquor to obtain compound 2 -Methyl-4-thiamphenyl-3-(2-(p-tolyloxy)ethoxy)benzoic acid 1,3-dimethyl-1-H-pyrazole-5-ester (III-1) .

[0168] In the same way, various intermediates (III) can be synthesized using different starting materials (I) and (II).

[0169] In the same way, various intermediates (VI) can be synthesized using different starting materials (I) and (V).

Embodiment 2

[0170] Example 2, (5-hydroxyl-1,3-dimethyl-1-H-pyrazole-4-)(2-methyl-4-thiamphenicol-3-(2-(p-tolyloxy) Synthesis of Ethoxyphenyl) Ketone (IV-1)

[0171] Dissolve 0.2 moles of compound (III-1) obtained in Example 1 in acetonitrile, add 0.28 moles of triethylamine and 0.02 moles of acetone cyanohydrin, continue stirring at room temperature for 12 hours, TLC detects that the transposition reaction is complete, concentrate and remove the solvent, add Dissolve in water, acidify to PH=2 with 1N dilute hydrochloric acid, extract with dichloromethane and dry to obtain compound (IV-1).

[0172] In the same way, various intermediates (IV) can be synthesized using different starting materials (III).

[0173] In the same way, various intermediates (VII) can be synthesized using different starting materials (VI).

Embodiment 3

[0174] Embodiment 3, the preparation of compound E-166

[0175] 0.010 moles of compound (IV-1) obtained in Example 2 and 0.012 moles of triethylamine were dissolved in tetrahydrofuran, and the tetrahydrofuran solution of 0.010 moles of sec-butyl chloroformate was added dropwise under ice-cooling, and stirring was continued at room temperature for 4 hours, and TLC detected that After the reaction was complete, it was filtered, concentrated and desolvated, and then separated by silica gel chromatography to obtain compound E-166.

[0176] In the same way, various compounds in which the substituent X is a direct bond can be synthesized using different starting materials (IV) and chloroformate.

[0177] In the same way, various compounds in which the substituent X is a direct bond can be synthesized using different starting materials (VII) and chloroformate.

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Abstract

The invention discloses substituted phenyl ketone compounds with ether structure and having structural formula (I-1) or (I-2); the structural formula and substituted groups of the compounds refer to the attachment. The substituted phenyl ketone compounds with ether structure are applicable to weeding.

Description

technical field [0001] The invention belongs to the field of herbicides and relates to a substituted phenyl ketone compound with an ether structure. Background technique [0002] The long-term use of existing pesticides has led to the resistance of diseases to them, which has led to a significant increase in the use of pesticides and caused serious damage to the environment. Therefore, it is required to continuously discover new pesticides with new mechanisms of action, for example, new pesticides with higher activity on insecticide, bactericide or acaricide. [0003] For herbicides, the prior art has carried out structural modification of existing herbicides from two aspects. On the one hand, structural modification of herbicides targeting HPPD enzymes such as mesotrione and sulcotrione based on the triketone structure, such as patents DE10130709, WO0218331, WO0248121, WO03106448, WO0202536, JP2002114776, WO0218352, WO03066607, WO20030122766, WO740 DE19846792, DE10301110,...

Claims

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Application Information

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IPC IPC(8): C07D231/20C07D405/12C07D409/12A01N43/56A01P13/00
CPCA01N43/56C07D231/20C07D405/12C07D409/12
Inventor 许天明彭伟立徐小燕钟良坤董德臻徐永华姚燕飞
Owner ZHEJIANG RES INST OF CHEM IND CO LTD
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