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Aromatic cyclopentenopyridine as well as synthesis method and application thereof

A technology of cyclopentenopyridine and synthesis method, which is applied in the field of pesticides, can solve the problems of limited synthesis and application, and achieve the effect of inhibiting tobacco mosaic virus and excellent anti-plant virus activity

Active Publication Date: 2019-08-23
INST OF APPLIED CHEM JIANGXI ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Most of the reported methods for the synthesis of cyclopentenopyridines have many limitations, such as the need for multi-step reactions, high pressure, the need to use anhydrous reagents or toxic transition metal catalysts, etc., which limit their synthetic applications.

Method used

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  • Aromatic cyclopentenopyridine as well as synthesis method and application thereof
  • Aromatic cyclopentenopyridine as well as synthesis method and application thereof
  • Aromatic cyclopentenopyridine as well as synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 8.00 g (35.4 mmol) of genipin, 10.89 g (38.9 mmol) of 2-iodobenzoic acid (IBX) and 200 ml of dimethyl sulfoxide were added to a 500 mL round bottom flask. Under argon protection, after electromagnetic stirring at room temperature for 3 h, 300 mL of water was added. Suction filtration, the filtrate was extracted four times with ethyl acetate, the organic phases were combined, washed with water, washed with saturated brine, dried over anhydrous magnesium sulfate, suction filtered, and precipitated to obtain the crude product of 2, and the pure product of compound 2 was obtained by column chromatography.

[0030] Compound 2 (1.00 g, 4.46 mmol), primary amine (4.46 mmol) and 60 mL of n-butanol were added to a 100 mL round bottom flask. After heating to reflux for 5 h, n-butanol was removed with a rotary evaporator. The target compound 3 was obtained by neutral alumina column chromatography, that is, the mangolin derivative—aromatic cyclopentenopyridine.

[0031]

[003...

Embodiment 2

[0055] Biological activity Take the activity of anti-tobacco mosaic virus (TMV) as an example,

[0056] 1. Virus purification and concentration determination:

[0057] 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.

[0058] 2. Preparation of compound (mangolin derivatives - aromatic cyclopentenopyridine) solution:

[0059] After weighing, the original drug was dissolved in DMF to prepare 1×10 5 μg / mL mother solution, and then diluted to the required concentration with an aqueous solution containing 1‰ Tween 80; ribavirin preparations were directly diluted with water.

[0060] 3. In vivo protection:

[0061] Select Shanxi tobacco with uniform growth at the 3-5...

Embodiment 3

[0077] Insecticidal activity test:

[0078] 1. Activity test of diamondback moth larvae

[0079] The leaf dipping method proposed by the International Resistance Action Committee (IRAC) was used. Weigh 2 mg of drug sample on an analytical balance into a 10 mL small beaker, add 50 μL of dimethylformamide (analytical grade) to dissolve, add 10 mL of water to make a 200 mg / kg drug solution. Immerse the cabbage leaves with straight ophthalmic tweezers for 2-3 seconds, and shake off the remaining liquid. 1 tablet each time, 3 tablets in total for each sample. Place the samples on the processing paper in the order they are marked. After the liquid medicine dries, put it into a marked 10cm long straight tube, insert the 2nd instar diamondback moth larvae, and cover the tube mouth with gauze. Put the test treatment in the standard treatment room, and check the results after 96 hours. Each compound was repeated 3 times. For the control, only emulsifier and solvent were added to d...

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Abstract

The invention relates to a cerbera manghas aldehyde derivative, namely cyclopentenopyridine, as well as a synthesis method and application thereof in plant protection, and belongs to the technical field of pesticides. The invention finds that a natural product, namely cerbera manghas aldehyde, has activity of plant virus prevention, insect killing and sterilization for a fist time, the natural product can be used as a novel plant source pesticide or can be developed as a lead compound, and secondly, a simple and efficient synthesis method for preparing cyclopentenopyridine from genipin as a raw material is found. Plant virus activity resistance tests of the cyclopentenopyridine provided by the invention show that the cyclopentenopyridine has activity on tobacco mosaic viruses, and the activity is prior to that of the lead compound cerbera manghas aldehyde; and insect killing and sterilization activity tests show that most compounds have very good activity on plutella xylostella, and inaddition have activity on 14 plant pathogenic bacteria.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to a natural product marmandal and its derivative-aromatic cyclopentenopyridine, to a synthesis method of cyclopentenopyridine, and to its application in plant protection. Background technique [0002] As the global population continues to increase and people's dietary structure changes, the pressure on food production is also increasing. Diseases, insects, and weeds pose a great threat to food production, and need to be continuously and effectively prevented. At the same time, the environmental, toxicological and management requirements for the application of agrochemical products are becoming increasingly stringent, and the requirements for pest control products are also increasing. The continuous development of pest resistance to control agents further limits the application of drugs. Therefore, it is necessary to continuously discover and develop new, effective ...

Claims

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Application Information

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IPC IPC(8): C07D221/04A01N43/42A01P3/00A01P1/00A01P7/04
CPCA01N43/42C07D221/04
Inventor 李玲邹吉勇游胜勇崔红敏谌开红邓朝阳
Owner INST OF APPLIED CHEM JIANGXI ACAD OF SCI
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