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5-substituted methylpyrrolidine-2, 4-diketone compound and use thereof

A kind of technology of methyl pyrrolidine and compound, applied in the field of herbicide preparation

Inactive Publication Date: 2011-05-11
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The latest research shows that the 5th position of TeA has an important influence on the herbicidal activity, but there are few reports on improving its herbicidal activity by modifying the 5th position

Method used

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  • 5-substituted methylpyrrolidine-2, 4-diketone compound and use thereof
  • 5-substituted methylpyrrolidine-2, 4-diketone compound and use thereof
  • 5-substituted methylpyrrolidine-2, 4-diketone compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Preparation of 3-(1-hydroxyethylidene)-5-(4-methoxybenzoylmethyl)pyrrolidine-2,4-dione (6f)

[0042] Equipped with thermometer, electric stirring (sealed), constant pressure dropping funnel, with CaCl 2 Add methyl N-acetoacetyl-2-(4-methoxybenzoylmethyl)-2-aminoacetate (0.1mol), 30mL methanol, sodium methoxide ( 2.3gNa+30mL methanol), refluxed for 2h, desolvated under reduced pressure, added 50mL of water, and repeatedly extracted with ethyl acetate to remove impurities until the extract was basically colorless. Acidify to pH 2 with 3M HCl, extract with ethyl acetate, anhydrous MgSO 4 Drying, suction filtration, precipitation, the residue was recrystallized from methanol to give a yellow solid 3-(1-hydroxyethylidene)-5-(4-methoxybenzoylmethyl)pyrrolidine-2,4-di Ketones (6f). Its physical parameters and spectral data are:

[0043] 3-(1-Hydroxyethylidene)-5-(4-methoxybenzoylmethyl)pyrrolidine-2,4-dione (6f): Yield: 71%; Yollow powder; m.p.160.6-162.0 °C; I...

Embodiment 2

[0047] Example 2: Preparation of 2-(4-(1-hydroxyethylidene)-3,5-dioxypyrrolidin-2-yl)butyl acetate (12a)

[0048] Equipped with thermometer, electric stirring (sealed), water separator, with CaCl 2 Add 2-(4-(1-hydroxyethylidene)-3,5-dioxypyrrolidin-2-yl)acetic acid (0.1mol), several drops of concentrated sulfuric acid, Butanol (0.4mol), 30mL benzene and 10mL DMF, stirred, heated, refluxed for 4h, desolventized, and the residue was recrystallized with methanol to obtain a white solid 2-(4-(1-hydroxyethylidene)-3, 5-Dioxypyrrolidin-2-yl)butyl acetate (12a). Its physical parameters and spectral data are:

[0049] 2-(4-(1-hydroxyethylidene)-3,5-dioxypyrrolidin-2-yl)butyl acetate (12a).Yeild: 80%; Colorless powder; m.p.61.8-62.3℃; (c 0.50, methanol); IR (KBr, cm -1 )v: 3428, 3216, 3060, 2958, 2935, 2873, 1738, 1710, 1664, 1620, 1451, 1331, 1219, 1175, 899, 733, 645; 1 H NMR (400MHz, CDCl 3 )δ (ppm): 6.37 (br, 1H, CHNH), 4.16-4.14 (m, 3H, CHNH+OCH 2 ), 3.03 (d, J=17.3Hz, 1H,...

Embodiment 3

[0060] Example 3: Preparation of 3-(1-hydroxyethylidene)-5-(butylthiomethyl)pyrrolidine-2,4-dione (18a)

[0061] Equipped with thermometer, electric stirring (sealed), constant pressure dropping funnel, with CaCl 2 Add N-acetoacetyl-2-butylthiomethyl-2-aminoacetic acid methyl ester (0.1mol), 30mL methanol, sodium methoxide (2.3g Na+30mL methanol) into the 250mL four-necked flask of the reflux tube of the drying tube , refluxed for 2 hours, desolvated under reduced pressure, added 50 mL of water, and extracted repeatedly with ethyl acetate to remove impurities until the extract was basically colorless. Acidify to pH 2 with 3M HCl, extract with ethyl acetate, Na 2 SO 4 After drying, suction filtration and solvent extraction, the residue was recrystallized from methanol to obtain 3-(1-hydroxyethylidene)-5-(butylthiomethyl)pyrrolidine-2,4-dione (18a) as a white solid. Its physical parameters and spectral data are:

[0062] 3-(1-Hydroxyethylidene)-5-(butylthiomethyl)pyrrolidine...

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Abstract

The invention relates to a 5-substituted methylpyrrolidine-2, 4-diketone compound and the use thereof. The structure of the 5-substituted methylpyrrolidine-2, 4-diketone compound is shown in a general formula (I), wherein R1, R2 and R3 are defined as the specification. The compound with the structure shown in the general formula (I) belongs to the technical field of applying compound to pesticide and can be used for preparing phytocide.

Description

1. Technical field [0001] The invention relates to a 5-substituted methylpyrrolidine-2,4-dione compound and its application, belongs to the technical field of compound synthesis applied to pesticides, and has the application of preparing herbicides. 2. Background technology [0002] Many natural substances with biological activity have been applied in plant protection. Scientists have found that natural tetramic acids have good biological activity, and Tenuazonic acid (5-sec-butyl-3-(1-hydroxyethylidene)pyrrolidin-2,4-one, TeA) is a typical one It has become one of the research focuses because of its good anticancer, antibacterial, herbicidal, antiviral and herbicidal activities. Especially its herbicidal activity has attracted the attention of agrochemical scientists. TeA has obvious activity against monocotyledon and dicotyledonous plants. A more in-depth study revealed that TeA is a novel inhibitor of photosynthetic system II that inhibits Q A to Q B Electron transpor...

Claims

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Application Information

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IPC IPC(8): C07D207/44C07D513/04C07D498/04C07D487/04C07D471/04A01N43/36A01N43/90A01P13/00
Inventor 杨春龙韩宝峰石清明王先锋强胜刘建波
Owner NANJING AGRICULTURAL UNIVERSITY
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