Application of A ring-modified new 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 problems such as product development stage, limited nutritional value and shelf life loss, etc., and achieve the effects of unique mode of action, high bactericidal activity, and human and animal safety.

Active Publication Date: 2019-05-07
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 process of crop production and product storage, causing serious losses to the developmental stage, nutritional value, limited shelf life and other issues of the product

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: the synthesis of compound ZX-1

[0016]

[0017] The synthetic method of compound ZX-1 of the present invention is carried out according to the following reaction formula:

[0018]

[0019] Synthesis of target compound ZX-1: Dissolve o-toluenebenzaldehyde (0.5mmol) in an appropriate amount of ethanol, then add indole (0.5mmol) and p-toluenesulfonic acid (0.5mmol), and heat to reflux for 24h. After cooling to room temperature, adjust the pH to alkaline with NaOH (1M) solution, then extract 3 times with dichloromethane, collect the organic phase and dry it with anhydrous magnesium sulfate, remove dichloromethane by rotary evaporation, column chromatography (dichloromethane methane / methanol=50:1) to obtain an orange-red solid, which is the target compound ZX1 (see literature for the synthesis method: Chemical Science, 2011, 2, 2178-2181).

[0020] Orange-red solid; Yield: 62%; m.p.105.32-106.54°C; 1 H NMR (400MHz, DMSO-d 6 )δ8.64(s,1H),8.03(d,J=7.5Hz...

Embodiment 2

[0021] Embodiment 2: the synthesis of compound ZX-2

[0022] The synthesis method is the same as in Example 1, except that 5-fluoro-2-(methylamino)benzaldehyde is used instead of o-toluidine.

[0023]

[0024] Orange-red solid; Yield: 70%; m.p.143.46-144.16°C; 1 H NMR (400MHz, DMSO-d 6 )δ8.85(s,1H),8.10(d,J=7.6Hz,1H),7.97(ddd,J=12.6,9.2,3.8Hz,2H),7.71(td,J=8.8,3.0Hz,1H ), 7.58(d, J=7.9Hz, 1H), 7.50(t, J=7.6Hz, 1H), 7.18(t, J=7.4Hz, 1H), 4.28(s, 3H). 13 C NMR (101MHz, DMSO-d 6 )δ156.04, 155.68, 133.82, 129.61, 128.51, 128.27, 123.89, 121.99, 121.28, 119.72, 119.20, 118.95, 117.63, 117.42, 114.44, 33.45. MS-ESI m / z: calcd for C 16 h 11 FN 2 :250.09[M+H] + .

Embodiment 3

[0025] Embodiment 3: the synthesis of compound ZX-3

[0026] The synthesis method is the same as in Example 1, except that 5-chloro-2-(methylamino)benzaldehyde is used instead of o-toluidine.

[0027]

[0028] Red solid; Yield: 50%; m.p.166.28-166.78°C; 1 H NMR (400MHz, DMSO-d 6 )δ8.83(d, J=5.5Hz, 1H), 8.18(t, J=3.5Hz, 1H), 8.10(d, J=7.5Hz, 1H), 7.96(d, J=9.0Hz, 1H) ,7.81(dt,J=6.7,3.3Hz,1H),7.59(d,J=7.9Hz,1H),7.50(t,J=7.6Hz,1H),7.19(t,J=7.4Hz,1H) ,4.26(d,J=4.1Hz,3H). 13 C NMR (101MHz, DMSO-d 6 )δ155.93, 155.62, 135.66, 130.57, 129.66, 128.80, 128.45, 128.06, 126.21, 124.09, 122.00, 121.71, 119.94, 117.78, 117.41, 33.37. MS-ESI m / z: calcd for C16 h 11 ClN 2 :266.06[M+H] + .

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Abstract

The invention relates to the field of natural medicinal chemistry and the technical field of biological pesticides, and discloses an application of any compound of A ring-modified new cryptolepine derivative ZX-1 to ZX-12 in the prevention and control or resisting of agricultural plant diseases. Bioactivity test shows that the compounds of the present invention have significant inhibitory activityagainst the following six plant diseases: Rape Sclerotinia Rot, Rhizoctonia solani, tomato gray mold, wheat scab, rice blast and watermelon blight, and parts of the compounds have better pathogen inhibition activity than azoxystrobin, and can be developed as leading molecules for natural source alkaloid bactericides. The compound of the present invention are derived from natural structural derivatives of the plant C. sanguinolenta, so the compounds have the characteristics of non-pollution, safety and high efficiency, has the advantages of natural source pesticides, can be developed into botanical pesticides suitable for producing green and pollution-free agricultural products, and belong novel biogenic pesticides.

Description

technical field [0001] The invention belongs to the field of natural medicinal chemistry and biopesticide technology, and discloses a new application of a ring-modified neo-elephine derivative, in particular to derivatives ZX-1 to ZX-12 in the prevention and treatment of Sclerotinia sclerotiorum , Rhizoctonia solani, tomato gray mold, wheat head blight, rice blast, watermelon blight caused by plant diseases. Background technique [0002] At present, plant diseases caused by fungi are mainly controlled by chemicals. Although many commercial fungicides have better control effects, the "3R" problem is becoming more and more serious due to the widespread use of these chemical pesticides, which has caused extreme social concern. big concern. Therefore, the research and development of new pesticides with high efficiency, low toxicity and low residue that can effectively control harmful organisms has become the primary goal of pesticide creation. As a part of biological pesticide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/90A01P3/00
Inventor 刘映前朱佳凯李俊采马强杨冠洲赵中敏彭静文冯建雄
Owner LANZHOU UNIVERSITY
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