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Spirooxoindole acylhydrazone derivative and preparation method thereof, and application of spirooxoindole acylhydrazone derivative in aspects of controlling plant viruses and killing bacteria and pests

A technology of indoleyl hydrazones and derivatives, applied in the field of pesticides, can solve the problems that the anti-plant virus activity, bactericidal activity and insecticidal activity are not reported in literature, etc., and achieve excellent anti-plant virus activity, high in vitro anti-TMV activity, The effect of good living activity

Active Publication Date: 2018-02-02
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As far as we know, there are no literature reports on the anti-plant virus activity, bactericidal activity and insecticidal activity of spiro-epoxy indole compounds in the field of pesticides.

Method used

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  • Spirooxoindole acylhydrazone derivative and preparation method thereof, and application of spirooxoindole acylhydrazone derivative in aspects of controlling plant viruses and killing bacteria and pests
  • Spirooxoindole acylhydrazone derivative and preparation method thereof, and application of spirooxoindole acylhydrazone derivative in aspects of controlling plant viruses and killing bacteria and pests
  • Spirooxoindole acylhydrazone derivative and preparation method thereof, and application of spirooxoindole acylhydrazone derivative in aspects of controlling plant viruses and killing bacteria and pests

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1: Synthesis (2-18) of hydrazide (1) and spirocyclic indole hydrazone derivatives

[0060]

[0061] Synthesis of (S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid

[0062] Add L-tryptophan (30 g, 0.147 mol), NaOH (5.88 g, 0.147 mol) and 400 mL of water into a 1 L single-necked flask, and stir until clear. Then 18 mL of 30% formaldehyde aqueous solution was added, stirred at room temperature for 2 h, and then heated to reflux for 3 h. After cooling, the pH value was adjusted to 5 with 2 mol / L hydrochloric acid solution. At this time, a precipitate was formed, which was filtered, washed and dried to obtain 24.58 g of a khaki solid, with a yield of 77.4%. 1 H NMR (400MHz, DMSO-d 6 )δ10.96(s, 1H), 7.44(d, J=7.5Hz, 1H), 7.33(d, J=7.3Hz, 1H), 7.07(t, J=7.2Hz, 1H), 6.99(t, J=7.6Hz, 1H), 4.31-4.20(m, 2H), 3.64(dd, J=9.6, 4.4Hz, 1H), 3.35(brs, 1H), 3.15(dd, J=15.8, 4.4Hz, 1H ), 2.83 (dd, J=15.7, 10.7Hz, 1H).

[0063] Synthesis of (S)-2,3,4,9-tetr...

Embodiment 2

[0108] Embodiment 2: the synthesis (19) of spiro ring oxide indolehydrazone derivatives

[0109]

[0110] (3S,5'S)-N'-benzylidene-1'-methyl-2-oxospiro[indoline-3,3'-pyrrolidine]-5'-formylhydrazone (19)

[0111] Methyl β-carbolinecarboxylate B (4.10g, 17.8mmol) was dissolved in 50mL of methanol, and aqueous formaldehyde (5.0mL, 37wt% aq) sodium cyanoborohydride (2.79g, 44.5mmol) was added thereto under stirring conditions , stirred at room temperature for 2h. Then add saturated NaHCO to the reaction system 3 Aqueous solution (150 mL), the aqueous phase was extracted with ethyl acetate (3 x 75 mL), and the organic phases were combined. Wash the organic phase with saturated brine (30mL), anhydrous MgSO 4 Dry and desolvate under reduced pressure. Column chromatography separation (petroleum ether: ethyl acetate = 1:1) gave white solid F in 71% yield. 1 H NMR (400MHz, CDCl 3 )δ8.18(s, 1H), 7.46(d, J=7.3Hz, 1H), 7.23(d, J=8.4Hz, 1H), 7.15-7.05(m, 2H), 3.96(d, J=15.1 Hz, 1H)...

Embodiment 3

[0114] Embodiment 3: the synthesis (20-23) of spiro ring oxide indolehydrazone derivative

[0115]

[0116] (3S, 3'R, 7a'S)-2'-((E)-(4-chlorobenzylidene) amino)-3'-(4-chlorophenyl)-2', 3', 7 ',7a'-tetrahydrospiro[indoline-3,6'-pyrrolo[1,2-c]imidazole]-1',2(5'H)-dione (20)

[0117] Add 4-chlorobenzaldehyde (0.36 g, 2.56 mmol) and a catalytic amount of glacial acetic acid to a solution of hydrazide compound 1 (0.30 g, 1.22 mmol) in 35 mL of ethanol, heat the reaction solution to reflux for 3 h, and monitor the reaction by TLC. After the reaction was complete, the reaction liquid was concentrated under reduced pressure. Column chromatography (petroleum ether: ethyl acetate = 3:1) yielded compound 20 in 81%. White solid (dr=27:1), melting point 127-129°C. 1 H NMR (400MHz, CDCl 3 )δ9.84(s, 1H), 8.88(s, 1H), 7.61(d, J=8.3Hz, 2H), 7.48-7.27(m, 7H), 7.12-7.00(m, 2H), 6.84(d , J=7.5Hz, 1H), 5.76(s, 1H), 4.43(dd, J=9.2, 4.6Hz, 1H), 3.50(s, 2H), 2.82(dd, J=13.6, 4.6Hz, 1H) , 2.50...

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Abstract

The invention relates to a spirooxoindole acylhydrazone derivative and a preparation method thereof, and an application of the spirooxoindole acylhydrazone derivative in the aspects of controlling plant viruses and killing bacteria and pests. The spirooxoindole acylhydrazone derivative has a formula with groups defined in the specification. The spirooxoindole acylhydrazone derivative provided by the invention shows excellent plant-virus resisting activity and has broad-spectrum bactericidal and pesticidal activities.

Description

technical field [0001] The invention relates to spiro-epoxyindole hydrazone derivatives, a preparation method thereof and applications in plant virus prevention and control, bactericidal and insecticidal aspects, and belongs to the technical field of pesticides. Background technique [0002] The spirooxindole skeleton structure widely exists in natural products and drug molecules. Spiro-epoxy indole alkaloids have a wide range of biological activities, for example: (-)-Horsfiline is a spiro-epoxy indole alkaloid isolated from Horsfieldia superba, which has obvious Analgesic effect; Spirotryprostatin A is isolated from Aspergillus fumigatus, it can inhibit the G2M cycle of mammalian tsFT210 cells, and then inhibit the proliferation of the cells; Strychnofoline is isolated from the leaves of Strychnosus ambarensis The alkaloid has inhibitory effect on the mitotic process of mouse melanoma cells and Ehrlich tumor cells. [0003] [0004] At present, the research on spirocy...

Claims

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Application Information

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IPC IPC(8): C07D487/10C07D487/20A01N43/90A01P1/00A01P3/00A01P7/04
CPCA01N43/90C07D487/10C07D487/20
Inventor 汪清民陈琳伟宋红健刘玉秀谢佳林
Owner NANKAI UNIV
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