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Oxime ether compound with strigolactones activity and application thereof

A compound and an independent technology, applied in the field of plant growth regulators, can solve the problems of complex structure, low strigolactone content, cumbersome synthesis steps, etc.

Active Publication Date: 2022-03-11
BEIJING UNIV OF AGRI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The content of natural strigolactone in plants is extremely low, its structure is complex, and its stability is poor, so it is difficult to obtain a large amount of strigolactone by means of separation and extraction
Artificial chemical synthesis has become the main means of obtaining strigolactones at present. However, the structure of natural strigolactones is complex, the synthesis is difficult, the cost is high, and large-scale preparation cannot be realized. Therefore, the molecular design of SLs functional analogues It is particularly important to solve the problem of its application in agricultural production with chemical synthesis
At present, the most effective and widely used SLs analogue is GR24. The existing GR24 synthesis route mainly uses 1-indanone as raw material. The synthesis steps are cumbersome and the yield is low, which leads to high production cost and limits the Its large-scale promotion and application in agricultural production

Method used

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  • Oxime ether compound with strigolactones activity and application thereof
  • Oxime ether compound with strigolactones activity and application thereof
  • Oxime ether compound with strigolactones activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1, Preparation of 2-fluoro-N-((4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxy)benzyl iminocyanide (compound 5)

[0050] Weigh 5g (36.93mmol) of o-fluorophenylacetonitrile into a 250mL round-bottomed flask, pressurize and pump 35mL of anhydrous N,N-dimethylformamide into it with magnetic stirring to dissolve it, and slowly add potassium tert-butoxide at 0°C 9.1g (81.38mmol), then add isoamyl nitrite 9.4g (81.38mmol), and the reaction system returns to room temperature and reacts for 4h; TLC [V 石油醚 : V 乙酸乙酯=2:1] After monitoring the reaction, add dilute hydrochloric acid at 0°C to adjust the pH to neutral, extract 3×30mL with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate; filter with suction, concentrate under reduced pressure, pass through the column layer Analysis and purification, V 石油醚 : V 乙酸乙酯 =4:1, a yellow solid was obtained, yield: 81%.

[0051] Weigh 1g (6.09mmol) of the reaction product from the previous step, add 20ml of anh...

Embodiment 2

[0052] Example 2, (Z)-4-methyl-N-((4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxy)benziminocyanide (compound 7)

[0053] Weigh 5g (38.12mmol) of p-tolueneacetonitrile into a 250mL round-bottomed flask, pressurize and pump 35mL of anhydrous N,N-dimethylformamide into it with magnetic stirring to dissolve it, and slowly add tert-butanol at 0°C Potassium 9.1g (83.86mmol), then add isoamyl nitrite 9.4g (83.86mmol), reaction system returns to reaction 4h under room temperature; TLC [V 石油醚 : V 乙酸乙酯 =2:1] After monitoring the reaction, add 30mL of dilute hydrochloric acid at 0°C, extract 3×30mL with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate; filter with suction, concentrate under reduced pressure, and purify by column chromatography, V 石油醚 : V 乙酸乙酯 =4:1, white solid was obtained, yield: 84%

[0054] Weigh 1 g (7.62 mmol) of the oximated product of p-tolueneacetonitrile, dissolve it in anhydrous N,N-dimethylformamide (20 ml), add 5-bromo-3-methyl-2- (5...

Embodiment 3

[0063] Embodiment 3, compound promotes the biological activity assay of sunflower rowang seed germination

[0064] Sunflower rowdang seeds were sterilized successively with 70% (v / v) ethanol and 0.5% sodium hypochlorite for 1 min and 15 min, respectively. Then rinse it several times with sterile water and dry it naturally in an ultra-clean workbench. The filter paper was placed in a Petri dish (diameter d=9 cm) and 1 ml of sterile water was added. Place three pieces of glass fiber filter paper with a diameter of d=13mm on the filter paper, and drop the test solution on the glass fiber filter paper. In all experiments, GR24rac was used as a positive control, and ethanol was used as a negative control, wherein GR24rac was a mixture of racemic isomers of (2'r) and (2's), and 6 replicates were set for each treatment. Place 30-80 sunflower leydang seeds on each piece of glass fiber filter paper, and then cultivate them in the dark at 25-26°C. On the 10th day, the number of radic...

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Abstract

The invention relates to an oxime ether compound with strigolactones activity and application of the oxime ether compound. The structural formula is as shown in formula I in the specification. The oxime ether compound as shown in the formula I is simple in structure, good in stability and excellent in plant growth regulation activity, the preparation method is simple and feasible, and large-scale production and application are facilitated.

Description

technical field [0001] The invention relates to oxime ether compounds with strigolactone activity and uses thereof, belonging to the field of plant growth regulators. Background technique [0002] Strigolactones (SLs) are a new class of plant endogenous hormones, which are terpene lactones with a unique tetracyclic structure and widely exist in higher plants. In 1966, Cook et al. isolated and identified a substance strigol from cotton root exudates that could induce germination of rhizome parasitic plant Striga, which was later named Strigaol. Subsequently, some compounds related to strigolide were discovered one after another, all of which are germination promoters of parasitic seeds. The natural strigolactones that have been isolated include sorghumolactone, strigolactone, Lidanol, etc. Up to 36 kinds. [0003] Until 2005, the biological function of strigolactone on the host plant was not proved. Akiyama et al. found that strigolactone is a plant-derived signal that ind...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/60C07D405/12C07D409/12A01N43/08A01N43/10A01N43/40A01P21/00
CPCC07D307/60C07D405/12C07D409/12A01N43/08A01N43/10A01N43/40
Inventor 赵汗青于春欣段留生李润枝王少君何东杰王晔蒋禹陈自力李兴佳苏宝财
Owner BEIJING UNIV OF AGRI