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Application of 2,8-bis(trifluoromethyl)quinoline 4-modified derivatives in prevention and treatment of plant diseases

A trifluoromethyl, quinoline-based technology, applied in the field of natural medicinal chemistry, can solve the problems of increasing chemical resistance of pathogens, human health and environmental pollution, adverse effects of non-target organisms, etc.

Pending Publication Date: 2019-08-23
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, repeated and individual use of chemical-based fungicides tends to increase the chemical resistance of pathogens, adversely affect non-target organisms, and pose potential risks to human health and environmental pollution

Method used

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  • Application of 2,8-bis(trifluoromethyl)quinoline 4-modified derivatives in prevention and treatment of plant diseases
  • Application of 2,8-bis(trifluoromethyl)quinoline 4-modified derivatives in prevention and treatment of plant diseases
  • Application of 2,8-bis(trifluoromethyl)quinoline 4-modified derivatives in prevention and treatment of plant diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: Synthetic method and chemical structure of 3a series compound

[0023]

[0024] In a dry 100mL round-bottomed flask, add 2,8-bis(trifluoromethyl)-4-hydroxyquinoline, then add an appropriate amount of phosphorus trichloride, stir at room temperature for 3 hours, and then remove it by rotary evaporation under reduced pressure. Phosphorus trichloride. Ice water was slowly dropped into the round bottom flask, and the resulting compound was extracted several times with dichloromethane. Collect the organic phase, dry it with anhydrous magnesium sulfate to remove the water in the solvent, hang it dry, and proceed to the next experiment directly.

[0025] The reactants obtained in the previous step and different substituent compounds were dissolved in ethanol and refluxed in a 100mL round-bottomed flask, and a small amount of triethylamine was added as a catalyst to react for about 3 hours, and the reaction was monitored by TLC. After the reaction was complet...

Embodiment 2

[0068] Embodiment 2: Synthetic method and chemical structure of 3b series compound

[0069]

[0070] In a dry 100mL round-bottom flask, add 2,8-bis(trifluoromethyl)-4-hydroxyquinoline, then add an appropriate amount of phosphorus trichloride, stir at room temperature for 3 hours, and then rotary evaporate under reduced pressure to remove three Phosphorus chloride. Ice water was slowly dropped into the round bottom flask, and the resulting compound was extracted several times with dichloromethane. The organic phase was collected, dried with anhydrous magnesium sulfate to remove the water in the solvent, spin-dried and directly proceeded to the next experiment.

[0071] First dissolve sodium hydride in anhydrous tetrahydrofuran (if the reaction yield is very low, then change the solvent to DMF), then slowly add different amines under ice bath conditions, activate for a period of time, finally add the compound obtained in the previous step, and The reaction was stirred at ro...

Embodiment 3

[0091] Embodiment 3: Synthetic method and chemical structure of 3c series compound

[0092]

[0093] In a dry 100mL round-bottomed flask, add 2,8-bis(trifluoromethyl)-4-hydroxyquinoline, then add an appropriate amount of phosphorus trichloride, stir at room temperature for 3 hours, and then remove it by rotary evaporation under reduced pressure. Phosphorus trichloride. Ice water was slowly dropped into the round bottom flask, and the resulting compound was extracted several times with dichloromethane. The organic phase was collected, dried with anhydrous magnesium sulfate to remove the water in the solvent, spin-dried and directly proceeded to the next experiment.

[0094] The reactants obtained in the previous step and different amines were dissolved in ethanol and refluxed in a 100mL round-bottomed flask, and a small amount of triethylamine was added as a catalyst to react for about 3 hours, and the reaction was monitored by TLC. After the reaction was completed, it was...

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Abstract

The invention discloses 2,8-bis(trifluoromethyl)quinoline 4-modified derivatives, a preparation method thereof and an application of the derivatives in prevention and treatment of plant diseases. Thetest results show that the compounds have excellent control effect on sclerotiniasclerotiorum, rhizoctonia solani, wheat phytoalexin, pyriculariaoryzae, phyllostictazeae, botrytis cinerea, watermelongummy stem blight and cotton fusarium wilt. The derivatives of the invention are simple in preparation process, low in price and easy to obtain raw materials, high in product purity and wide in bactericidal spectrum, and are expected to be developed into a new bactericide.

Description

technical field [0001] The invention belongs to the field of natural medicinal chemistry and pesticide technology, and discloses a new application of a 2,8-bis(trifluoromethyl)quinoline derivative modified at the 4-position, specifically relating to the use of quinoline compounds in Prevention and control of Sclerotinia sclerotiorum, Rhizoctonia solani, Fusa Humgraminearum, Magnaporthe oryzae, Phyllosticta zeae, Botrytis cinerea ( Plant diseases caused by Botrytis cinerea), Mycosphaerlla melonis and Fusarium oxysporum f.sp.vasinfectum. Background technique [0002] Plant diseases caused by fungi can cause significant losses to agriculture and pose a serious threat to global food security. Fungal pathogens often cause crop rot and even produce mycotoxins that are harmful to humans and animals. To control these plant diseases, various chemical fungicides have been produced. However, repeated and individual use of chemical-based fungicides often increases the chemical resist...

Claims

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Application Information

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IPC IPC(8): C07D215/42C07D215/46C07D215/44C07D401/12C07D413/04C07D215/233C07D215/36A01N43/42A01N43/60A01N43/84A01N47/06A01N43/653A01N43/647A01P3/00
CPCC07D215/42C07D215/46C07D215/44C07D401/12C07D413/04C07D215/233C07D215/36A01N43/42A01N43/60A01N43/84A01N47/06A01N43/653A01N43/647
Inventor 刘映前杨冠洲燕银芳李虎朱佳凯高建梅尹晓丹
Owner LANZHOU UNIVERSITY
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