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Application of A-ring modified cryptoxine derivative in prevention and treatment of agricultural plant diseases

A technology of selemenine and derivatives, applied in the field of natural medicinal chemistry, can solve the problems of enhancing and threatening human health and environmental safety, etc.

Inactive Publication Date: 2020-12-22
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the severe outbreak of plant diseases and the widespread and continuous use of chemical fungicides, the resistance of plant pathogens to fungicides has increased, which seriously threatens human health and environmental safety.

Method used

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  • Application of A-ring modified cryptoxine derivative in prevention and treatment of agricultural plant diseases
  • Application of A-ring modified cryptoxine derivative in prevention and treatment of agricultural plant diseases
  • Application of A-ring modified cryptoxine derivative in prevention and treatment of agricultural plant diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Embodiment 1: the synthesis of target compound L-1

[0014]

[0015] For the synthesis method, please refer to the literature method: Org.Lett.2017,19(16):4275-4278. The specific synthesis operation is as follows: Synthesis of intermediate 1: dissolve indole (30mmol) in acetonitrile, keep the system at 0°C and add 60 % sodium hydride (42mmol), add p-toluenesulfonyl chloride (33mmol) after stirring for 10 minutes, stir at room temperature for 4 hours, add saturated ammonium chloride aqueous solution to stop the reaction, then extract with ethyl acetate, wash with brine, combine the organic phases, and After drying over magnesium sulfate, it was filtered, and the organic phase was concentrated under reduced pressure to obtain a solid residue, which was purified by column chromatography using petroleum ether / ethyl acetate as eluent to obtain a white solid product.

[0016] Synthesis of Intermediate 2: Add Intermediate 1 (11mmol) and distilled water (110mmol) to 110mL of...

Embodiment 2

[0021] Embodiment 2: the synthesis of target compound L-2

[0022]

[0023] The experimental procedure is the same as in Example 1, only 4-chloro-N-methylaniline is used instead of N-methylaniline. Yield: 37%; purple-red powdery solid; 1 H NMR (400MHz, DMSO-d 6 )δ:8.88(s,1H),8.55(d,J=9.6Hz,1H),8.51(d,J=2.4Hz,1H),8.47(d,J=8.5Hz,1H),7.86(dd, J=9.4,2.5Hz,1H),7.66(d,J=8.5Hz,1H),7.55(t,J=7.6Hz,1H),7.05(t,J=7.5Hz,1H),4.90(s, 3H). 13 C NMR (100MHz, DMSO-d 6 )δ: 160.94, 145.29, 139.88, 131.46, 131.30, 128.85, 128.49, 127.98, 125.66, 125.60, 125.19, 119.59, 119.37, 117.29, 114.15, 39.88. MS-ESI m / z: C 16 h 11 ClN 2 :267.0[M+H] + .

Embodiment 3

[0024] Embodiment 3: the synthesis of target compound L-3

[0025]

[0026] The experimental procedure is the same as in Example 1, except that 4-methoxy-N-methylaniline is used instead of N-methylaniline. Yield: 38%; red-black powdery solid; 1 H NMR (400MHz, DMSO-d 6 )δ:8.81(d,J=4.5Hz,1H),8.50–8.46(m,1H),8.45(d,J=5.5Hz,1H),7.85–7.75(m,1H),7.64(d,J =8.6Hz,1H),7.53(dd,J=8.0,5.7,4.0Hz,2H),7.04(t,J=7.5Hz,1H),4.91(s,3H),3.95(s,3H). 13 C NMR (100MHz, DMSO-d 6)δ: 155.69, 145.29, 138.48, 130.41, 128.90, 126.33, 125.25, 124.93, 121.53, 119.17, 118.58, 116.59, 114.31, 107.25, 56.09, 39.48. MS-ESI m / z: C 17 h 14 N 2 O:263.1[M+H] + .

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Abstract

The invention discloses application of any compound of A-ring modified cryptolepine derivatives L-1 to L-10 in prevention and treatment of agricultural plant diseases. Activity test results show thatthe compound has potential inhibitory activity on four plant diseases such as sclerotinia rot of colza, rhizoctonia solani, botrytis cinerea and wheat scab, especially has an excellent antibacterial effect on botrytis cinerea, and is expected to be developed as a novel specific bactericide.

Description

technical field [0001] The invention belongs to the field of natural medicinal chemistry, and discloses a new application of a ring-A modified phyllophylline derivative, and specifically relates to the use of a ring-A modified phyllophylline derivative in the prevention and treatment of rapeseed sclerotinia and tomato cinerea disease, Rhizoctonia solani, and wheat head blight. Background technique [0002] According to statistics, plant fungal diseases cause about 10% of the world's main crop production reduction every year, and economic losses amount to hundreds of billions of dollars. Not only that, plant diseases also pose a huge threat to my country's agricultural development and food security. Losses already exceeded production by 11%. For example, my country's potato production areas are affected by late blight, resulting in a 10% to 40% yield reduction every year; wheat is affected by scab, causing a 10% to 30% yield reduction every year. Due to the severe outbreak o...

Claims

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Application Information

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IPC IPC(8): A01N43/90A01P3/00
CPCA01N43/90
Inventor 刘映前刘华燕银芳陈永甲马强彭静文赵中敏周锐王仁轩尹晓丹白银鹏孙钰马鲲原
Owner LANZHOU UNIVERSITY
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