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Tryptophan derivative, preparing method and application in preventing and treating plant viruses, killing bacteria and killing insects

A technology of tryptophan and its derivatives, applied in the field of pesticides, can solve the problems of poor therapeutic effect and achieve excellent anti-plant virus activity

Active Publication Date: 2016-08-24
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the drug inhibited only less than 50% at a concentration of 500 μg / mL
Ningnanmycin produced by microbial fermentation is currently the best anti-plant virus disease agent, but Ningnanmycin only has a preventive effect, and its therapeutic effect is poor

Method used

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  • Tryptophan derivative, preparing method and application in preventing and treating plant viruses, killing bacteria and killing insects
  • Tryptophan derivative, preparing method and application in preventing and treating plant viruses, killing bacteria and killing insects
  • Tryptophan derivative, preparing method and application in preventing and treating plant viruses, killing bacteria and killing insects

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Example 1: Synthesis of (S)-2-amino-3-(1H-indole-3)-propionic acid methyl ester (1)

[0072]

[0073] Add 10 g (49.02 mmol) of L-tryptophan and 150 mL of methanol into a 250 mL single-necked round bottom flask, add 10 mL of thionyl chloride dropwise with stirring, and then stir under heating and reflux for 4 hours. TLC monitors that the reaction is complete and the solution is removed. The obtained solid is washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, filtered, and removed to obtain 9.16 g of a brown solid with a melting point of 90-91°C and a yield of 86%. 1 H NMR(300MHz, CDCl 3 )δ8.47(s, 1H, Ar-NH), 7.60(d, 3 J HH =7.8Hz, 1H, Ar-H), 7.32(d, 3 J HH = 8.1 Hz, 1H, Ar-H), 7.18 (t, 3 J HH =7.2Hz, 1H, Ar-H), 7.11(t, 3 J HH =7.2Hz, 1H, Ar-H), 7.00(s, 1H, Ar-H), 3.82(dd, 3 J HH =4.8Hz, 2 J HH 7.5Hz, 1H, CH), 3.71(s, 3H, CH) 3 ), 3.28(dd, 3 J HH =4.5Hz, 2 J HH =14.4Hz, 1H, CH 2 ), 3.04(dd, 3 J HH =7.5H...

Embodiment 2

[0077] Example 2: Synthesis of (S)-2-amino-N-butyl-3-(1H-indole-3-)propionamide (I-3)

[0078]

[0079] Add 0.40g (1.83mmol) methyl ester 1,10mL n-butylamine to a 25mL single-necked round-bottom flask, stir at room temperature for 2d, desolvate, add dichloromethane / water liquid extraction, dry the organic phase with anhydrous sodium sulfate, filter, Dissolve and drain to obtain 0.33 g of yellow viscous liquid with a yield of 70%. 1 H NMR(300MHz, CDCl 3 )δ8.14(s, 1H, Ar-NH), 7.69(d, 3 J HH =7.8Hz, 1H, Ar-H), 7.38(d, 3 J HH =7.8Hz, 1H, Ar-H), 7.21(t, 3 J HH =7.5Hz, 1H, Ar-H), 7.13(t, 3 J HH =7.5Hz, 1H, Ar-H), 7.08(s, 1H, Ar-H), 3.71(dd, 3 J HH =9.0Hz, 3.9Hz, 1H, CH), 3.40(dd, 3 J HH =3.9Hz, 2 J HH =14.4Hz, 1H, CH 2 ), 3.25(q, 3 J HH =6.6Hz, 1H, CH 2 ), 2.91(dd, 3 J HH =9.0Hz, 2 J HH =14.4Hz, 1H, CH 2 ), 1.57-1.20(m, 4H, CH 2 CH 2 ), 0.91(t, 3 J HH =7.5Hz, 3H, CH 3 ); 13 C NMR(100MHz, CDCl 3 )δ174.7, 136.4, 127.5, 123.1, 122.2, 119.5, 119.0, 111.8, 111.3, 55.7, 38.8, 31.6, ...

Embodiment 3

[0080] Example 3: (S)-1-(2-hydroxyethylamino)-3-(1H-indole-3-)-1-oxopropan-2-ammonium hydrochloride (I-4) synthesis

[0081]

[0082] Add 0.50g (2.29mmol) of methyl ester 1,10mL ethanolamine to a 25mL single-necked round-bottom flask, stir at room temperature for 2.5d, transfer the reaction solution to a 100mL single-necked flask, add enough ethanol to desolvate, and dissolve the obtained solid with dichloromethane HCl gas was passed into the liquid, a yellow solid was precipitated, cooled, filtered, and the mother liquor was desolvated. DCM / MeOH=5:1 (v / v) was used as the eluent for column chromatography to obtain a yellow solid 0.32 g. The yield is 49%, and the melting point is 118-120°C. 1 H NMR(400MHz, DMSO-d 6 )δ10.92(s, 1H, NH), 8.03(t, 3 J HH =4.8Hz, 1H, O=C-NH), 7.57(d, 3 J HH =8.0Hz, 1H, Ar-H), 7.34(d, 3 J HH =8.0Hz, 1H, Ar-H), 7.17(d, 4 J HH =1.6Hz, 1H, Ar-H), 7.06(t, 3 J HH =7.6Hz, 1H, Ar-H), 6.97(t, 3 J HH =7.6Hz, 1H, Ar-H), 4.75 (br, 1H, OH), 3.49 (dd, 3 J HH ...

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Abstract

The invention relates to a tryptophan derivative (I), a preparing method of the tryptophan derivative (I), and application of the tryptophan derivative (I) in preventing and treating plant viruses, killing bacteria and killing insects. The formula of the tryptophan derivative (I) is shown in the description, and the meanings of all groups in the formula are shown in the description. The tryptophan derivative expresses especially excellent plant virus resisting activity, and also has broad-spectrum bactericidal activity and insecticidal activity.

Description

Technical field [0001] The invention relates to tryptophan derivatives and preparation methods and their applications in preventing and controlling plant viruses, sterilization and insecticide, and belongs to the technical field of pesticides. Background technique [0002] Tryptophan is divided into L-tryptophan and D-tryptophan according to its chirality. [0003] [0004] L-tryptophan has extremely important uses in food, medicine, and feed. First, L-tryptophan can be used as a food additive. L-tryptophan is one of the essential restrictive amino acids for the human body. It is very little synthesized in the body and needs to be taken from outside. In organisms, starting from L-chromophoric acid, bioactive substances such as 5-hydroxytryptamine, indole acetic acid, niacin, pigments, alkaloids and coenzymes can be synthesized. Secondly, L-tryptophan also has important applications in medicine. L-tryptophan can penetrate the blood-brain barrier, is converted to 5-hydroxytryptop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/20C07D401/12C07D405/12C07D417/12A01P3/00A01P7/04A01P1/00
Inventor 汪清民宋红健刘永贤黄源琼刘玉秀
Owner NANKAI UNIV
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