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Sanguinarine derivatives, chelerythrine derivatives and application thereof

A technology of chelerythrine and derivatives, applied in the directions of application, botanical equipment and methods, biocides, etc., to achieve the effects of excellent insecticidal activity, strong biological activity, and strong insecticidal activity

Inactive Publication Date: 2020-12-15
GUIZHOU MOUNT FANJING ECOLOGICAL AGRI INC
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] So far, there has been no research report on derivatives and activities of ni

Method used

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  • Sanguinarine derivatives, chelerythrine derivatives and application thereof
  • Sanguinarine derivatives, chelerythrine derivatives and application thereof
  • Sanguinarine derivatives, chelerythrine derivatives and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Embodiment 1: the preparation of compound 1-2

[0031] In a 250mL three-necked flask, add bolus sanguinarine (1g, 0.003mol), acetonitrile 50mL, and triethylamine (3eq.) to dissolve under magnetic stirring, then slowly add 1-n-butyl-3-phenyl-1H- 1,2,4-triazol-5-amine (0.0036mol, 1.2eq, 0.82g), after the addition is complete, stir at room temperature for 5h, after TLC detects that the reaction is complete, stop stirring, after the reaction solution is concentrated under reduced pressure, use V Ethyl acetate: V petroleum ether = 1:4 Flash column chromatography gave 0.70 g of light yellow oil with a yield of 43%.

[0032] Structural analysis of compound I-2: 1 H NMR (CDCl 3 ,300MHz)δ6.77(s,1H, NH),6.07(s,2H,CH 2 ),6.13(s,2H,CH2),5.04(s,1H,CH), 8.07~7.80(m,4H,Ph),7.51~7.38(m,4H,Ph),7.18~6.95(m,2H, Ph), 4.47 (d, J = 7.2Hz, 2H, CH2), 3.02 (s, 3H, CH3), 1.95 (d, J = 7.2Hz, 2H, CH 2 ), 0.89(t,J=7.50Hz,3H,CH 3 ); 13C NMR (CDCl 3 , 75MHz) Δ101.1.1.1.2, 144.5,148.5,147.4,148...

Embodiment 2

[0033] The preparation of embodiment 2 compound I-15

[0034] In a 250mL three-necked flask, add bolus sanguinarine (1g, 0.003mol), acetonitrile 50mL, and triethylamine (3eq.) to dissolve under magnetic stirring, then slowly add 1-n-propyl-3-(4-nitro Phenyl)-1H-1,2,4-triazol-5-amine (0.0036mol, 0.9g, 1.2eq), after the addition was completed, stirred at room temperature for 7h, after TLC detected that the reaction was complete, the stirring was stopped, and the reaction solution reduced After concentration under reduced pressure, flash column chromatography with V ethyl acetate: V petroleum ether = 1:4 gave 0.70 g of light yellow oil with a yield of 40%.

[0035] Structural analysis of compound I-15: 1 H NMR (CDCl 3 ,300MHz)δ6.79(s,1H, NH),6.07(s,2H,CH 2 ),6.12(s,2H,CH 2 ),5.04(s,1H,CH),8.07~7.81(m,4H,Ph),7.50~7.39(m,5H,Ph),7.18~6.97(m,2H,Ph),4.46(d,J= 7.2Hz, 2H, CH 2 ),3.02(s,3H,CH 3 ), 1.95 (d, J=7.2Hz, 2H, CH 2 ),1.26~1.25(m, 2H,CH 2),0.89(t,J=7.50Hz,3H,CH 3 ); 13...

Embodiment 3

[0036] Embodiment 3: the preparation of compound II-2

[0037] In a 250mL three-necked flask, add chelerythrine (1g, 0.003mol), 50mL of acetonitrile, triethylamine (3eq.) and dissolve under magnetic stirring, then slowly add 1-ethyl-3-(2- Chlorophenyl)-1H-1,2,4-triazol-5-amine (0.0036mol, 0.85g, 1.2eq), after the addition is complete, stir at 60°C for 4h, after TLC detects that the reaction is complete, stop stirring, and react After the solution was concentrated under reduced pressure, it was subjected to column chromatography with V ethyl acetate: V petroleum ether = 1:3 to obtain 0.60 g of white powder with a yield of 36%.

[0038] Structural analysis of compound I-15: 1 H NMR (CDCl 3 ,300MHz)δ6.79(s,1H, NH),6.13(s,2H,CH 2 ),5.06(s,1H,CH),7.81~7.61(m,4H,Ph),7.48~7.38(m,4H,Ph),7.18~6.97(m,2H,Ph),3.68(s,3H, CH 3 ),3.82(s,3H,CH 3 ), 3.97(d,J=7.2Hz,2H,CH 2 ),3.02(s,3H,CH 3 ), 1.54(t, J=7.51Hz, 3H, CH 3 ); 13 C NMR (CDCl 3 ,75MHz)δ101.2,147.4,148.1,158.3,160.1,132.2,1...

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Abstract

The invention belongs to the technical field of novel pesticides, and particularly relates to sanguinarine derivatives, chelerythrine derivatives and application thereof. According to the invention, anitrogen heterocyclic structure is introduced into natural macleaya cordata sanguinarine molecules and macleaya cordata chelerythrine molecules to synthesize a class of novel-structure substituted macleaya cordata sanguinarine derivatives and chelerythrine derivatives containing the nitrogen heterocyclic structure. Compared with sanguinarine and chelerythrine, the sanguinarine derivative and thechelerythrine derivative synthesized by the method disclosed by the invention have stronger biological activity; the sanguinarine derivatives have strong insecticidal activity on the green peach aphids, the corrected death rate of most sanguinarine derivatives is over 85%, the LC50 of part of sanguinarine derivatives is below 10g/mL, and the sanguinarine derivatives still have excellent insecticidal activity on the green peach aphids.

Description

technical field [0001] The invention belongs to the technical field of novel pesticides, and in particular relates to sanguinarine derivatives, chelerythrine derivatives and applications thereof. Background technique [0002] Chemical pesticides are indispensable pest control agents in agricultural planting. On the one hand, pesticides have a good effect on preventing and controlling pests and weeds, and are often used in chemical control methods in plant protection; on the other hand, chemical pesticides have toxic residues, Diseases and insects have developed resistance to pesticides and damaged ecosystems, which have brought serious harm to the environment and human beings. Due to the harmfulness of chemical pesticides, the research of new pesticides is of great significance to the development of modern green agriculture. [0003] There are many ways to create new pesticides, such as random screening, analogous synthesis, natural product models, and biological rational d...

Claims

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Application Information

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IPC IPC(8): C07D491/153A01N43/90A01P7/04
CPCA01N43/90C07D491/153
Inventor 贾长青马瑞梁浩张光明
Owner GUIZHOU MOUNT FANJING ECOLOGICAL AGRI INC
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