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Application of new D-ring-modified cryptolepine derivatives in prevention and control of agricultural plant diseases

A technology of selemenine and derivatives, applied in the field of natural medicinal chemistry, can solve the problems of product development stage, limited nutritional value and shelf life loss, etc., and achieve the effects of unique mode of action, excellent bacteriostatic effect and simple synthesis process

Inactive Publication Date: 2019-08-09
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Plant fungal diseases have always been one of the restrictive factors in the production of food crops and product storage, causing serious losses to the developmental stage, nutritional value, and limited shelf life of products.

Method used

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  • Application of new D-ring-modified cryptolepine derivatives in prevention and control of agricultural plant diseases
  • Application of new D-ring-modified cryptolepine derivatives in prevention and control of agricultural plant diseases
  • Application of new D-ring-modified cryptolepine derivatives in prevention and control of agricultural plant diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: Synthesis of compound ZXD-1

[0017]

[0018] The synthesis method of the compound ZXD-1 of the present invention is carried out according to the following reaction formula:

[0019]

[0020] Synthesis of the target compound ZXD-1: o-methylaminobenzaldehyde (0.5mmol) was dissolved in an appropriate amount of ethanol, followed by adding 5-methylindole (0.5mmol) and p-toluenesulfonic acid (0.5mmol), heating and refluxing for 24h. After cooling to room temperature, the pH was adjusted to alkaline with NaOH (1M) solution, and then extracted with dichloromethane three times. The organic phase was collected and dried with anhydrous magnesium sulfate. The dichloromethane was removed by rotary evaporation and column chromatography (dichloro Methane / methanol=50:1) was purified to obtain an orange-red solid, which is the target compound ZXD1 (for the synthesis method, see literature: Chemical Science, 2011, 2, 2178-2181).

[0021] Orange-red solid; Yield: 62%; 1 H NMR(400MHz...

Embodiment 2

[0022] Example 2: Synthesis of compound ZXD-2

[0023] The synthesis method is the same as in Example 1, except that 5-methoxyindole is used instead of 5-methylindole.

[0024]

[0025] Dark red solid; Yield: 51%; 1 H NMR(400MHz, DMSO-d 6 )δ8.94(s,1H),8.11(d,J=6.5Hz,1H),7.95(d,J=8.6Hz,1H),7.86-7.82(m,1H),7.75(d,J=2.7 Hz, 1H), 7.51 (d, J = 1.8 Hz, 1H), 7.48 (t, J = 3.8 Hz, 1H), 7.11 (d, J = 8.6 Hz, 1H), 4.26 (s, 3H), 3.85 ( s,3H). 13 CNMR(101MHz,DMSO-d 6 )δ154.56,154.08,148.61,137.08,131.32,130.47,130.11,127.29,124.36,122.32,120.52,117.65,117.17,115.31,105.95,56.06,33.34.MS-ESI m / z:calcdfor C 17 H 14 N 2 O:262.11[M+H] + .

Embodiment 3

[0026] Example 3: Synthesis of compound ZXD-3

[0027] The synthesis method is the same as in Example 1, except that 5-fluoroindole is used instead of 5-methylindole.

[0028]

[0029] Orange-red solid; Yield: 53%; 1 H NMR(400MHz, DMSO-d 6 )δ8.97(s,1H), 8.12(d,J=8.0Hz,1H),7.98(d,J=2.6Hz,1H),7.96(d,J=2.5Hz,1H),7.86(m, 1H), 7.56 (d, J = 8.6Hz, 1H), 7.50 (t, J = 7.4Hz, 1H), 7.31 (m, 1H), 4.28 (s, 3H). 13 C NMR(101MHz, DMSO-d 6 )δ158.28,155.96,151.90,137.32,131.54,130.82,130.59,127.08(d,J=4.3Hz),124.71(d,J=10.0Hz),122.32,120.36,118.16(d,J=8.6Hz),116.17 (d,J=24.1Hz),115.40,108.04(d,J=24.3Hz),33.19.MS-ESI m / z:calcd for C 16 H 11 FN 2 :250.09[M+H] + .

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Abstract

The invention relates to the field of natural pharmaceutical chemistry and the technical field of biological pesticide, discloses application of any one compound of new D-ring-modified cryptolepine derivatives ZXD-1-ZXD-18 in the preparation of pesticide for preventing and treating or resisting agricultural plant diseases, and belongs to novel biological source pesticide. A biological activity test shows that the compounds have obvious inhibitory activity on six plant diseases including sclerotinia rot of colza, rhizoctonia solani, tomato gray mold, wheat scab, rice blast and watermelon vine blight, and the inhibitory activity of a part of the compounds on germs is superior to that of azoxystrobin so that the compounds can be developed as pilot molecules of natural source alkaloid bactericides. Since the compounds derived from a natural structural derivative in a plant C. sanguinolenta have the characteristics of being free of pollution, safe and efficient and the advantages of naturalsource pesticide, the compounds can be developed into plant source pesticide suitable for producing green agricultural products free of pollution.

Description

Technical field [0001] The invention belongs to the field of natural medicine chemistry and the technical field of biological pesticides. It discloses a new use of a new leucophylline derivative modified by the D ring, and specifically relates to the use of derivatives ZXD-1 to ZXD-18 in the prevention and treatment of rape sclerotinia , Rhizoctonia solani, tomato gray mold, wheat head blight, rice blast, watermelon vine blight caused by plant diseases. Background technique [0002] At present, the prevention and control of plant diseases mainly relies on the use of chemical pesticides, which are favored by people because of their small dosage and quick effect. However, due to the fine development of the chemical industry and the inaccurate grasp of the farmers' medicine technology, the pursuit of effect is blindly increased. Dosage has caused the problem of "resistance, rampant, and pesticide residues" to become more and more serious. Therefore, research and development of high-...

Claims

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Application Information

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IPC IPC(8): C07D471/04A01P3/00
CPCC07D471/04
Inventor 刘映前朱佳凯赵中敏彭静文刘华陈永甲王仁轩
Owner LANZHOU UNIVERSITY
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