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Spirooxoindole (thio)hydantoin derivative as well as preparation method and application thereof to aspects of plant virus prevention and control, sterilization and insect killing

A technology of indole hydantoin and urea derivatives is applied in the field of pesticides, which can solve the problems of no literature reports on anti-plant virus activity, bactericidal activity and insecticidal activity, and achieve excellent anti-plant virus activity and good anti-TMV in vivo activity. Effect

Active Publication Date: 2017-11-17
山东博苑医药化学股份有限公司 +1
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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 (thio)hydantoin derivative as well as preparation method and application thereof to aspects of plant virus prevention and control, sterilization and insect killing
  • Spirooxoindole (thio)hydantoin derivative as well as preparation method and application thereof to aspects of plant virus prevention and control, sterilization and insect killing
  • Spirooxoindole (thio)hydantoin derivative as well as preparation method and application thereof to aspects of plant virus prevention and control, sterilization and insect killing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]Embodiment 1: the synthesis (1-15) of spiroepoxide indole thiohydantoin derivative

[0039]

[0040] route one

[0041] Synthesis of (S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (A)

[0042] 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 solution was added, and heated to reflux for 3 h. After cooling, the pH was adjusted with 2mol / 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 (400 MHz, DMSO-d 6 )δ 10.96(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).

[0043] Synthesis of (S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic aci...

Embodiment 2

[0082] Example 2: Synthesis of spiro-epoxyindole thiohydantoin derivatives (16, 17)

[0083]

[0084] route two

[0085] Compounds 16 and 17 were synthesized according to compound 1.

[0086] (3S, 5'R, 7a'R)-5'-methyl-2'-phenyl-3'-thio-2',3',7',7a'-tetrahydrospiro[indoline- 3,6'-pyrrolo[1,2-c]imidazole]-1',2(5'H)-dione (16)

[0087] Yellow powder, yield 84.3%, melting point 135-137°C. 1 H NMR (400MHz, CDCl 3 )δ 9.61(s, 1H), 7.57-7.48(m, 5H), 7.30(s, 1H), 7.22-7.17(m, 1H), 7.10-7.05(m, 1H), 6.75(d, J=7.7 Hz, 1H), 4.96-4.89(m, 2H), 2.72(d, J=7.7Hz, 2H), 1.44(d, J=6.9Hz, 3H). 13 C NMR (100MHz, CDCl 3 for C 20 h 17 N 3 o 2 S(M+H) + 364.1114, found 364.1118.

[0088] (3R, 5'S, 7a'R)-5'-methyl-2'-phenyl-3'-thio-2',3',7',7a'-tetrahydrospiro[indoline- 3,6'-pyrrolo[1,2-c]imidazole]-1',2(5'H)-dione (17)

[0089]Yellow powder, yield 68.9%, melting point 106-109°C. 1 H NMR (400MHz, CDCl 3 ( m, 1H), 5.56-5.50 and 5.19-5.13 and 4.96-4.88, 4.53-4.46 (m, 2H), 3.46-3.28 (m...

Embodiment 3

[0090] Embodiment 3: the synthesis (18) of spiroepoxide indole thiohydantoin derivative

[0091]

[0092] Refer to compound 1 for the synthetic operation steps of route 3 compound 18.

[0093] (3S, 5′S)-1′-(tert-butylthiocarbamoyl)-2-oxospiro[indoline-3,3′-pyrrolidine]-5′-methyl carboxylate ( 18)

[0094] White powder, yield 45.7%, melting point 108-110°C. 1 H NMR (400MHz, CDCl 3 )δ 9.44(s, 1H), 7.26 (t, J=7.4Hz, 1H), 7.13(d, J=7.2Hz, 1H), 7.06(t, J=7.4Hz, 1H), 7.01(d, J =7.7Hz, 1H), 5.78(s, 1H), 5.32(t, J=8.2Hz, 1H), 4.00(d, J=9.8Hz, 1H), 3.82(s, 1H), 3.79(s, 3H ), 2.61-2.51(m, 1H), 2.47-2.36(m, 1H), 1.52(s, 9H). 13 C NMR (100MHz, CDCl 3 )δ 180.2, 177.7, 172.4, 140.1, 132.3, 129.0, 123.5, 122.7, 110.6, 62.4, 56.9, 54.4, 52.8, 52.7, 39.0, 29.0. HRMS (ESI) calcd for C 18 h 23 N 3 o 3 S(M+H) + 362.1533, found 362.1538.

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Abstract

The invention relates to a spirooxoindole (thio)hydantoin derivative as well as a preparation method and application thereof to aspects of plant virus prevention and control, sterilization and insect killing. A structural formula of the derivative is a structure shown as a general formula I. The spirooxoindole (thio)hydantoin derivative provided by the invention has excellent plant virus resisting activity and also has broad-spectrum sterilization activity and insect killing activity. (The formula I is shown in the description.).

Description

technical field [0001] The invention relates to a spiroepoxide indole hydantoin (thio) urea derivative, a preparation method thereof, and an application in plant virus prevention, 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 Hors fieldia 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 cell; Strychnofoline is obtained from the leaves of Strychnosus ambarensis Isolated, the alkaloid has an inhibitory effect on the mitotic process of mouse melanoma cells and Ehrlich tumor cells. [0003] [0004] At present, the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/20C07D487/10A01N43/90A01P1/00A01P3/00A01P7/00A01P7/04
CPCA01N43/90C07D487/10C07D487/20
Inventor 汪清民宋红健陈琳伟李成林于国清
Owner 山东博苑医药化学股份有限公司
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