3-acyl-pyrrolidine-2,4-diketo compound and herbicidal activity

A technology of acylpyrrolidine and compounds, applied in the field of 3-acylpyrrolidine-2, can solve the problems of no specific record of compound herbicidal activity, no specific record, etc., and achieve excellent selectivity, selectivity improvement, high The effect of herbicidal activity

Inactive Publication Date: 2005-10-05
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Although the above-mentioned documents describe 3-acylpyrrolidine-2,4-dione compounds, there is no specific description of the 3-acylpyrrolidine-2,4-dione compounds mentioned in this patent. There is no specific description of the herbicidal activity of these compounds

Method used

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  • 3-acyl-pyrrolidine-2,4-diketo compound and herbicidal activity
  • 3-acyl-pyrrolidine-2,4-diketo compound and herbicidal activity
  • 3-acyl-pyrrolidine-2,4-diketo compound and herbicidal activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Synthesis of 1-isopropyl-3-(3-methylbenzoyl)pyrroline-2,4-dione

[0034] In a 150ml four-neck flask, 20 millimoles of ethyl 3-methylbenzoyl acetate and 30 millimoles of ethyl N-isopropylglycinate were stirred and reacted in 70 milliliters of benzene at 80°C for 10 hours, and then cooled to room temperature. Add 30 mmol sodium methoxide solution and stir at room temperature for 20 hours. After the solvent was removed under reduced pressure, a crude product of the target compound was obtained. The pure product is obtained by column chromatography.

Embodiment 2

[0035] Example 2: Synthesis of 1-tert-butyl-3-(3-methylbenzoyl)pyrroline-2,4-dione

[0036] In a 150ml four-neck flask, 20 millimoles of ethyl 3-methylbenzoyl acetate and 30 millimoles of ethyl N-tert-butylglycinate were stirred and reacted in 70 milliliters of benzene at 80°C for 12 hours and then cooled to room temperature. Add 37 mmol sodium methoxide solution and stir at room temperature for 20 hours. After the solvent was removed under reduced pressure, the crude product of the target compound was obtained. The pure product is obtained by column chromatography.

Embodiment 3

[0037] Example 3. Synthesis of 5-methyl-3-(2-methoxybenzoyl)pyrroline-2,4-dione

[0038] In a 150ml four-neck flask, 20 millimoles of ethyl 3-methoxybenzoyl acetate and 30 millimoles of ethyl 3-methylglycinate hydrochloride were stirred and reacted in 70 milliliters of benzene at 80°C for 46 hours, and then cooled After reaching room temperature, 41 mmol sodium methoxide solution was added and stirred at room temperature for 20 hours. After the solvent was removed under reduced pressure, a crude product of the target compound was obtained. The pure product is obtained by column chromatography.

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Abstract

This invention relates to 3-acyl-pentazane-2,4-diketo compound. The compound (I) has high plant growing restraining and weed killing reactivity, and shows good selectivity to the plants. It can be the weed killing solvent in the broad-leave field to remove single-leave weed. There into, R1 : H, alkyl, alkoxyl alkyl, alkylogen, alkylogen alkoxyl alkyl, substituted aromatic base and etc; R2R4: H, alkyl, alkoxyl, phenyl alkoxyl, hydroxyl alkyl, alkoxyl, alkylogen, alkylogen alkoxyl, nitryl, cyan and etc, R2, R4 can be the same or different; R3: substituted phenyl, substituted naphthyl, substituted pyridyl, substituted thiazolyl, cyan and etc.

Description

Technical field [0001] The present invention relates to 3-acylpyrrolidine-2,4-dione compounds and herbicidal activity. Background technique [0002] 4-hydroxyphenylpyruvate dioxygenase (HPPD) exists in various organisms and is extracted. It is an iron-tyrosine protein that can catalyze p-hydroxypyruvate in plants It is converted into urogentisic acid, and then into plastoquinone and tocopherol, which are important substances required for electron transfer in photosynthesis. Plastoquinone is also a key auxiliary factor affecting the catalysis of phytoene desaturase. At the same time, because the inhibitor of this enzyme, 2-(2-nitro-4-trifluoromethylbenzoyl-1,3-dione, has been used in the clinical treatment of tyrosinopathy, it has no adverse effects on the human body. After ALS, ACC and Protox, it has become another new herbicide target enzyme and a clinical target enzyme for the treatment of tyrosinosis. Since 1982, the company found that the high-efficiency triketone corn field ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/38C07D207/36
Inventor 杨华铮朱有全邹小毛胡方中刘斌杨秀凤
Owner NANKAI UNIV
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