Matrine derivatives, synthesis thereof, and application thereof in control of plant diseases and pests

A derivative, matrine technology, applied in the field of agricultural protection, to achieve the effect of easy synthesis, good environmental compatibility and good water solubility

Active Publication Date: 2019-03-05
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Matrine derivatives, synthesis thereof, and application thereof in control of plant diseases and pests
  • Matrine derivatives, synthesis thereof, and application thereof in control of plant diseases and pests
  • Matrine derivatives, synthesis thereof, and application thereof in control of plant diseases and pests

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Synthesis of N-substituted-11-substituted matrine derivative compound 1 (method 1)

[0032]

[0033] method one

[0034] N-tert-butoxycarbonyl-11-dehydroxymatrine (C)

[0035] Extracted with ethyl acetate, combined the organic phases, washed with 80 mL of saturated brine, dried over anhydrous sodium sulfate, precipitated, and separated by column chromatography (DCM:MeOH=20:1) to obtain 3.00 g of a light yellow oily product with a yield of 81 %. Proceed directly to the next step.

[0036] 11-Dehydroxymatrine (D)

[0037] Extracted with ethyl acetate, combined the organic phases, washed with 80 mL of saturated brine, dried over anhydrous sodium sulfate, precipitated, and separated by column chromatography (DCM:MeOH=20:1) to obtain 1.20 g of a pale yellow oily product, which solidified in air. Yield 77%, Mp 46-47°C. 1 H NMR (400MHz, CDCl 3 )δ3.25(t, J=12.0Hz, 1H, NCH 2 ), 3.09-3.03 (m, 1H, NCH), 2.80 (dd, J = 16.0, 12.0Hz, 2H, NCH 2), 2.63 (dd, J=1...

Embodiment 2

[0041] N-substituted-11 substituted matrine derivatives (compound 2-15) are completed with reference to the operation steps of Example 1 (see the attached figure 1 ):

[0042] Compound 2

[0043] White solid 0.30g, yield 75%, Mp 78-79°C. 1 H NMR (400MHz, CDCl 3 ) δ3.61 (d, J=4.0Hz, 1H, NCH), 3.44-3.39 (m, 1H, NCH 2 ), 3.29(t, J=12.0Hz, 1H, NCH 2 ), 2.91 (s, 3H, NCH 2 ), 2.74 (s, 2H, NCH 2 , NCH), 2.05-1.73 (m, 9H, CH 2 ), 1.59-1.26 (m, 10H, CH, CH 2 ), 0.92(t, J=4.0Hz, 3H, CH 3 ). 13 C NMR (100MHz, CDCl 3 )δ63.1, 57.3, 56.8, 56.7, 46.3, 39.7, 39.0, 34.2, 32.2, 28.4, 27.9, 27.7, 21.1, 20.9. HRMS (ESI) calcd for [C 16 h 30 N 2 o 2 S+H] + 315.2101, found 315.2190.

[0044] Compound 3

[0045] Yellow oily liquid, yield 76%. 1 H NMR (400MHz, CDCl 3 ) δ 9.07 (s, 1H, Py-H), 8.74 (d, J = 4.0Hz, 1H, Py-H), 8.14 (d, J = 8.0Hz, 1H, Py-H), 7.41 (dd, J=8.0, 4.0Hz, 1H, Py-H), 3.66 (dd, J=8.0, 4.0Hz, 1H, NCH), 3.53 (dd, J=8.0, 4.0Hz, 1H, NCH 2 ), 3.31-3.26 (m, 1H, NCH 2...

Embodiment 3

[0070] Example 3 Synthesis of N-substituted-11-substituted matrine derivatives (compound 16) (method 2)

[0071] N-substituted-11 substituted matrine derivatives (compounds 17-19) are completed by referring to the operation steps of Example 3 (see the accompanying drawings for the structural formula):

[0072]

[0073] Method Two

[0074] Compound 16

[0075] Add N-benzoyl-11-dehydroxymatrine (0.60g, 1.70mmol) to a 100mL round bottom flask, add lithium aluminum hydride (0.13g, 3.4mmol), heat up to reflux, and monitor the reaction by TLC after 6h Completely quenched in an ice-water bath, desolvated, added 20mL ethyl acetate, separated, the water phase was extracted with 3×40mL ethyl acetate, then washed with 60mL saturated brine, dried over sodium sulfate, desolventized to obtain a light yellow oily liquid 0.30 g, yield 79%. 1 H NMR (400MHz, CDCl 3 )δ7.34-7.20 (m, 5H, PhCH), 4.68 (s, 0.5H, NCH 2 Ph), 4.09 (d, J=12.0Hz, 0.5H, NCH 2 Ph), 3.04 (d, J=12.0Hz, 1H, NCH 2 Ph)...

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Abstract

The invention relates to compounds represented by the formula, and preparation and application thereof in pesticide. The invention provides a novel structure that can inhibit tobacco mosaic virus andkill bacteria and pests. The industrialization is easy and the synthesis is simple. N-substituted-11-substitited matrine derivatives have a good performance on inhibiting the activity of tobacco mosaic virus (protection, treatment, and passivation), and the definition of R is represented in the description.

Description

technical field [0001] The invention relates to matrine derivatives and their synthesis and application in preventing and controlling plant diseases and insect pests, belonging to the field of agricultural protection. Background technique [0002] Chemically synthesized pesticides, referred to as chemical pesticides, are a type of pesticides developed and synthesized by humans and produced by the chemical industry. Chemically synthesized pesticides have complex molecular structures, various varieties, and large production volumes. They are the mainstay of modern pesticides and have a wide range of applications. The efficacy of many varieties is very high, and because their main raw materials are petrochemical products, they are rich in resources and have a large output. Synthetic chemical pesticides can be divided into organic chlorine, organic phosphorus, organic mercury, organic arsenic, carbamate and other preparations according to their chemical composition. The toxicit...

Claims

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Application Information

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IPC IPC(8): C07D471/16A01P1/00A01P7/02A01P7/04A01P3/00
CPCC07D471/16
Inventor 汪清民倪婉君刘玉秀宋红健王兹稳
Owner NANKAI UNIV
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