3-substituted cyclopropane carbonyl pyrrolidine-2,4-diketone and herbicidal activity thereof

A cyclopropanecarbonyl pyrrolidine, diketone technology, applied in the directions of herbicides, algicides, biocides, plant growth regulators, etc., can solve problems such as no specific records, no compound herbicidal activity, etc.

Inactive Publication Date: 2010-11-24
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above documents describe 3-acylpyrrolidine-2,4-dione compounds, there is no specific description of the 3-substituted cyclopropany

Method used

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  • 3-substituted cyclopropane carbonyl pyrrolidine-2,4-diketone and herbicidal activity thereof
  • 3-substituted cyclopropane carbonyl pyrrolidine-2,4-diketone and herbicidal activity thereof
  • 3-substituted cyclopropane carbonyl pyrrolidine-2,4-diketone and herbicidal activity thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Synthesis of 1-isopropyl-3-(3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanyl)pyrrolidine-2,4-dione

[0025] In a 100ml four-necked bottle, 10 mmoles of 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanyl ethyl acetate and 15 mmoles of N-isopropylglycine ethyl ester, in Stir and react in 30 ml of benzene at 60°C for 10 hours, then cool to room temperature, add 20 mmol of sodium methoxide solution, and stir at room temperature for 20 hours. After removing the solvent under reduced pressure, the crude product of the target compound was obtained. The pure product was obtained by column chromatography.

Embodiment 2

[0026] Example 2: Synthesis of 1-allyl-3-(3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropaneformyl)pyrrolidine-2,4-dione

[0027] In a 150ml four-necked bottle, 20 mmoles of 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanoyl acetate and 30 mmoles of N-allyl glycine ethyl ester, in Stir and react in 70 ml of benzene at 80°C for 12 hours, then cool to room temperature, add 37 mmol of sodium methoxide solution, and stir at room temperature for 20 hours. After removing the solvent under reduced pressure, the crude product of the target compound was obtained. The pure product was obtained by column chromatography.

Embodiment 3

[0028] Example 3. 5-n-butyl-3-(3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropaneformyl)pyrroline-2,4-dione synthesis

[0029] In a 50ml four-necked bottle, 20 mmoles of 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanoyl acetate and 30 mmoles of 3-n-butylglycine ethyl ester hydrochloride salt, stirred and reacted at 80°C in 20 ml of benzene for 34 hours, cooled to room temperature, added 21 mmoles of sodium methoxide solution, and stirred at room temperature for 20 hours. After removing the solvent under reduced pressure, the crude product of the target compound was obtained. The pure product was obtained by column chromatography.

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PUM

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Abstract

The invention relates to 3-substituted cyclopropane carbonyl pyrrolidine-2,4-diketone and the herbicidal activity thereof. A compound (I) has high plant growth inhibition activity and herbicidal activity and shows up good selectivity to rapes, wherein R1 and R2 are CH3, Cl, Br or CF3, and R3 is -CH(CH3)2, -CH2CH2CH3, -CH(CH3)CH2CH3, -CH2CH2CH2CH3, CH2=CHCH2- or cyclo-C3H5.

Description

(1) Technical field [0001] The present invention relates to 3-substituted cyclopropanylpyrrolidine-2,4-dione compounds and their herbicidal activity. (2) Background technology [0002] 4-hydroxyphenylpyruvate dioxygenase (4-hydroxyphenylpyruvate dioxygenase, HPPD) exists in various organisms and has been extracted. It is an iron-tyrosine protein that can catalyze p-hydroxypyruvate in plants. It is converted into homogentisic acid, and then converted into plastoquinone and tocopherol, which are important substances required for electron transfer in photosynthesis. Among them, plastoquinone is also a key auxiliary factor affecting the catalysis of phytoene desaturase. In view of its above-mentioned important At the same time, because the enzyme inhibitor 2-(2-nitro-4-trifluoromethylbenzoyl-1,3-dione has been used in the clinical treatment of tyrosinosis, it has no adverse effects on the human body function, making it another new herbicide target enzyme after ALS, ACC and Prot...

Claims

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Application Information

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IPC IPC(8): C07D207/38A01N43/36A01P13/00
Inventor 朱有全张金袁燕伟谢利芬杨华铮邹小毛胡方中
Owner NANKAI UNIV
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