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Synthesis and application of lactone analogue with indoline-2-ketone skeleton

A technology of indoline and analogues, applied in the fields of application, organic chemistry, biocides, etc., can solve the problems of complex structures, manpower and material resources

Active Publication Date: 2022-04-19
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the structure of natural strigolactone analogs is complex and the separation and purification process consumes a lot of manpower and material resources, so it is difficult to apply in agricultural production

Method used

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  • Synthesis and application of lactone analogue with indoline-2-ketone skeleton
  • Synthesis and application of lactone analogue with indoline-2-ketone skeleton
  • Synthesis and application of lactone analogue with indoline-2-ketone skeleton

Examples

Experimental program
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Effect test

Embodiment 1

[0028]Synthetic route 1:

[0029] In a dry 100mL round bottom flask, NaH (1 eq, 60% in oil) was dissolved in 20mL xylene solution, and then the reaction system was heated at 130°C. After heating for 15 minutes, indolin-2-ones (1, 1 eq) substituted with halogens at positions 5 / 6 / 7 were slowly added to the reaction system in batches, and then the reaction system was refluxed. After refluxing for 1 h, dimethyl sulfate (1 eq) was slowly added to the reaction system, and the reaction was continued at 130° C. for another hour. After the reaction, the reaction system was cooled to room temperature, and then extracted with ethyl acetate. The collected organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered with suction, and precipitated to obtain a crude product. The crude product was separated by column chromatography (PE:EA=2:1, v / v) to obtain the pure intermediate 2 (orange solid, yield 55%).

[0030] In a pre-dried 100mL round bottom flask, ...

Embodiment 2

[0049] Compounds W-1~W-24 were tested for the germination activity of melon radang and sunflower radang seeds, and the test method was as follows:

[0050] Take a disposable plastic Petri dish with a diameter of 9 cm, lay a piece of filter paper on the bottom layer and moisten it with sterilized distilled water, and then cover it with a filter paper sheet with a diameter of 6 mm. Sprinkle the melon seeds evenly on the wet filter paper, and the number of seeds on the filter paper is about 25-65. Seal the Petri dish with sealant and pre-incubate the seeds for 3-7 days at room temperature in the dark. Take a glass fiber filter paper sheet with a diameter of 6 mm, place it in a plastic Petri dish and add 25 μL of the compound solution to be tested (acetone as a solvent), after the acetone is completely volatilized, take a pre-cultured seed piece and place it on top of it and add 25 μL of sterilized distilled water , and finally place a piece of filter paper moistened with sterili...

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Abstract

The invention relates to synthesis and application of a lactone analogue with an indoline-2-ketone skeleton. The structural general formula of the compounds is shown as a formula (I), R1 represents substituted halogen atoms fluorine, chlorine and bromine or unsubstituted hydrogen atoms, and R2 represents substituted methyl to n-amyl and aromatic ring or benzyl substituent on N atoms. The lactone analogue with an indoline-2-ketone parent nucleus structure is obtained by taking halogen substituted indoline-2-ketone or indoline-2, 3-diketone as a raw material and synthesizing through 2-3 steps. Orobanche coerulescens seeds are used as control objects, a series of compounds are applied to seed germination activity tests, and the compounds have good seed germination activity, can be applied to seed germination of parasitic weed Orobanche coerulescens, and can be used for developing a suicide type herbicide of parasitic weed Orobanche coerulescens. The invention further discloses application of the weeding composition in preventing and treating parasitic weed diseases such as orobanche coerulescens or striga asiatica in combination with agriculturally acceptable auxiliaries, synergists or commercial herbicides.

Description

technical field [0001] The invention relates to the synthesis of a lactone analogue with an indolin-2-one skeleton and its application in agriculture to prevent and control parasitic weeds Redang and Striga. Background technique [0002] Strigolactones were identified as a new type of plant hormone in 2008 after auxin, gibberellin, cytokinin, abscisic acid, gibberellin and ethylene. This type of phytohormone plays a vital role in regulating the growth and development of plants. Because of its important physiological and biochemical effects, the research of this kind of compound has also received extensive attention from chemists and biologists all over the world. [0003] The first compound (+)-Strigol ((+)-Strigol) that can stimulate the germination of the parasitic weed Striga was extracted from the root exudate of cotton by Cook in 1966, and the compound was obtained in 1972. The approximate configuration, and finally the absolute configuration of the compound was deter...

Claims

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Application Information

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IPC IPC(8): C07D405/12A01N43/38A01P21/00A01P13/00
CPCC07D405/12A01N43/38Y02A40/10
Inventor 徐效华徐妞妞卢强辉金钟康允饶谢龙观
Owner NANKAI UNIV
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