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Glycosyl substituted genipin derivative as well as preparation method and application thereof

A technology of genipin and derivatives, which is applied to a class of glycosyl-substituted genipin derivatives and their preparation and application fields, to achieve excellent insecticidal activity and excellent bactericidal activity

Active Publication Date: 2018-01-12
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, no chemical pesticide has been able to completely cure plants once they are infected with TMV

Method used

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  • Glycosyl substituted genipin derivative as well as preparation method and application thereof
  • Glycosyl substituted genipin derivative as well as preparation method and application thereof
  • Glycosyl substituted genipin derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: Synthesis of I-a-1~I-a-9

[0027] Synthesis of 1-hydroxygenipin (1): Add genipin (500mg, 2.21mmol), pyridine (0.267mL, 3.315mmol) and dichloromethane (22mL) into a 100mL round bottom flask. Under the protection of argon, the reaction temperature was lowered to 0° C., and pivaloyl chloride (0.299 mL, 2.431 mmol) was added dropwise. After the addition was complete, the reaction was heated up and stirred overnight. After the reaction was completed, saturated ammonium chloride was added to the organic phase to quench the reaction, and the organic phase was washed with 5% copper sulfate aqueous solution and saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, separation by column chromatography (petroleum ether: ethyl acetate = 5:1) gave 551 mg of a gray solid, with a yield of 80%.

[0028] Target compound (I-a-1): Add glycosyl trichloroacetimidate (2, 1mmol), 1-hydroxygenipin (1, 1mmo...

Embodiment 2

[0041] Embodiment 2: Synthesis of I-b-1~I-b-9

[0042] Synthesis of 7-hydroxygenipin (4): Add genipin (1.13g, 5mmol), silver nitrate (2.12g, 12.5mmol) and 30mL solvent N,N-dimethylformamide in a 100mL round bottom flask , tert-butyldimethylsilyl chloride (1.88 g, 12.5 mmol) was slowly added with stirring at 0° C., and the reaction was stirred overnight at room temperature. After the reaction was completed, the reaction system was filtered, the filtrate was poured into saturated aqueous sodium bicarbonate solution, and extracted three times with ether. The organic phases were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. Precipitation by filtration, column chromatography (petroleum ether: ethyl acetate = 40:1-5:1) yielded 334.5 mg colorless oil of monosubstituted product and 1.5 g colorless oil of double substituted product, total yield 86% . In a 100 mL round bottom flask, mono-substituted genipin (1.49 g, 3.28 mmol) was dissolved in 20 mL ...

Embodiment 3

[0057] Embodiment 3: the assay of anti-TMV activity, assay procedure is as follows:

[0058] 1. Virus purification and concentration determination:

[0059] Virus purification and concentration determination were carried out in accordance with the SOP specification for tobacco mosaic virus compiled by the Bioassay Laboratory of the Institute of Elements, Nankai University. After the crude virus extract was centrifuged twice with polyethylene glycol, the concentration was measured and refrigerated at 4°C for later use.

[0060] 2. Compound solution preparation:

[0061] After weighing, the original drug was dissolved in DMF to prepare 1×10 5 μg / mL stock solution, and then diluted to the required concentration with aqueous solution containing 1‰ Tween 80.

[0062] 3. In vitro therapeutic effect:

[0063] Rub inoculation of leaves of Shanxi tobacco at the right age, rinse with running water, the virus concentration is 10 μg / mL. After drying, cut it off, cut it in half along ...

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Abstract

The invention relates to a glycosyl substituted genipin derivative (I) as well as a preparation method and an application as pesticides. The inhibition rate of a part of compounds in formulae (Ia andIb) to tobacco mosaic viruses exceeds that of commercial variety virazole, and is approximate to that of ningnanmycin. In addition, a part of the compounds in the formulae (Ia and Ib) have excellent sterilization activity on 14 plant pathogens, and fungus bacteriosis of multiple crops can be effectively prevented and treated. A part of the compounds in the formulae (Ia and Ib) have excellent insecticide activity on 4 common lepidoptera pests (plutella xylostella, oriental armyworm, ostrinia nubilalis and cotton bollworm), and lepidoptera pests of multiple crops can be effectively prevented andtreated. Specific synthesis steps and bioactivity are shown in the specification.

Description

technical field [0001] The invention relates to a kind of glycosyl-substituted genipin derivatives, a preparation method thereof and an application as a pesticide. Background technique [0002] Botanical pesticides refer to pesticides made from plants or their active ingredients that are toxic to other plant diseases and insect pests (Guangdong Chemical Industry, 2013, 40, 68-69). Compared with traditional chemically synthesized pesticides, botanical pesticides have obvious advantages: (1) general botanical pesticides are easier to degrade in the environment; (2) have target specificity and are relatively safe to humans, animals and non-target organisms after use; 3) There are many active ingredients and unique mode of action, so it is difficult for pests to develop resistance; (4) The mode of action of some botanical pesticides is non-toxic, including attracting, repelling, refusal to feed, sterilization, regulating growth and development, etc. It has a wider mode of actio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/04C07H15/26C07H1/00A01N43/16A01P7/04A01P3/00A01P1/00
Inventor 汪清民夏青刘玉秀董建洋王强王兹稳宋红健李玲
Owner NANKAI UNIV
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