Application of new cryptolepine derivatives in controlling and preventing plant-derived germs

A technology of selemenine and derivatives, applied in the field of pesticides, can solve problems such as reduced use efficiency, and achieve the effects of high bactericidal activity, excellent bacteriostatic effect and high selectivity

Inactive Publication Date: 2018-12-28
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, chemical control is the main means to reduce the damage of rice blast, rape sclerotinia and gray mold, but the commercial fungicides currently used have different degrees of resistance to these diseases, resulting in reduced use efficiency
At presen

Method used

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  • Application of new cryptolepine derivatives in controlling and preventing plant-derived germs
  • Application of new cryptolepine derivatives in controlling and preventing plant-derived germs
  • Application of new cryptolepine derivatives in controlling and preventing plant-derived germs

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Synthetic method of intermediate

[0016]

[0017] The synthesis method of intermediates can be found in literature: (1) Lu, W.J., Kathryn, J.W., Wang Li, Kento Imai, et al. European Journal of Medicinal Chemistry, 2013, 64:498-511. (2) Ibrahim, E.S., Pieter , V.D.V., Steert, K., et al.Journal Medical Chemistry, 2009,52:2979-2988. Its specific synthetic operation is described in detail as follows:

[0018] The synthetic method of intermediate 2: pyridine (0.42mL) was added in the tetrahydrofuran (THF) (10mL) solution of indole (0.77mmol) under the condition of ice-bath, then the THF (5mL) solution of trichloroacetyl chloride (0.58mL) ) solution was slowly added dropwise into the above solution with a constant pressure funnel. The mixture was stirred at 25-30°C for 12h. After the completion of the reaction monitored by TLC, the reaction was quenched with 1M HCl (100mL) aqueous solution, extracted three times with ethyl acetate (3×100mL), the organic phase was combin...

Embodiment 2

[0043] The synthetic method of target compound 1a-3a

[0044]

[0045] For the synthesis method of the target compound 1a-3a, please refer to the literature: Ibrahim, E.S., Pieter, V.D.V., Steert, K., et al.. Journal Medical Chemistry, 2009, 52:2979-2988. The specific synthesis operation is described in detail as follows:

[0046] Put the above intermediate 4 (4-F / 4-Cl) (2.0mmol) in a round bottom flask, dissolve it with toluene (5mL), and add POCl after the dissolution is complete 3 (25.0mmol), refluxed at 110°C for 12h, after TLC monitored the reaction was complete, cooled to 25°C, spin-dried the toluene solution, washed with ice saturated NaHCO 3 Neutralize the product with an aqueous solution (maintain a neutral environment at 30°C), extract the organic phase with dichloromethane as the reaction solution, wash the organic phase with a saturated NaCl aqueous solution, combine the organic phases and wash with anhydrous NaCl 2 SO 4 After drying, the organic phase was spi...

Embodiment 3

[0057] The synthetic method of target compound 4a-24a

[0058]

[0059]

[0060] For the synthesis method of the target compound 4a-24a, please refer to the literature method: Mei, Z.W., Wang, L., Lu, W.J., etal. Journal Medical Chemistry, 2013, 56:1431-1442. The specific synthesis operation is described in detail as follows:

[0061] Put the above target compound 1a (2a / 3a) (1.0mmol) and the corresponding aminoalkylamine reagent (10.0mmol) in a round bottom flask, dissolve it with DMF (10mL), and wait until the temperature rises to 135-155°C It was refluxed for 1-4 hours, and after the completion of the reaction as monitored by TLC, the DMF was spin-dried under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate and methanol containing 2N ammonia as eluents.

[0062] Target compound 4a:

[0063]

[0064] Yellow solid; Yield: 84%; 1 H NMR (400MHz, CDCl 3 )δ8.47(1H,d,J=8.0Hz,Ar-H),8.28(1H,d,J=8.0Hz,Ar-H),7.68...

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PUM

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Abstract

The invention relates to the technical field of natural medicinal chemistry and biopesticide, and discloses application of any one compound of 1a-24a of new cryptolepine derivatives in the preparationof a medicament for controlling or resisting rice blasts, rape sclerotinia sclerotiorum and tomato grey mould. Since the compound is based on a bactericidal molecule obtained by natural alkaloid newcryptolepine separated from C. sanguinolenta, the compound has the advantage of a nature-derived pesticide of being capable of being developed into a plant-derived pesticide suitable for the production of green and pollution-free agricultural products, and belongs to a novel nature-derived biological pesticide.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and discloses a new application of a basaltine derivative, in particular to the application of a basaltine derivative as a natural source pesticide in the prevention and treatment of plant-derived pathogens. Background technique [0002] The rice blast fungus (Pyricularia oryae Cav.) is the most prevalent and destructive pathogen in rice producing areas worldwide. Rice blast causes an annual loss of 11% to 30% of rice production worldwide. Since the 1990s, the annual occurrence area of ​​rice blast in China has been 3.8 million ha 2 More than hundreds of millions of kilograms of paddy loss. Sclerotias clerotiorum (Lib.) de Bary) is a broad-spectrum disease that seriously endangers the yield and quality of rapeseed. Rapeseed output is reduced by 10% to 30%, and can reach 80% in severe cases, which reduces the quality of rapeseed and brings huge losses to production. In addition, gray mold ca...

Claims

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Application Information

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IPC IPC(8): A01N43/90A01P3/00
CPCA01N43/90
Inventor 刘映前张君香赵中敏马强冯建雄杨冠洲尚小飞
Owner LANZHOU UNIVERSITY
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