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A class of dithiocarbamate compound and its preparation method and application

A technology of dithiocarbamate and compound, which is applied in the field of chemical biology research, can solve the problems of difficult industrial production, high amino activity, inappropriate 5-aminopyrazole and the like

Active Publication Date: 2021-04-23
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the amino activity of 5-aminopyrazole derivatives is high, which will interfere with the reaction. At present, there is no technical method for introducing dithiocarbamate on the 5-aminopyrazole heterocycle
In the past, we developed a dithiocarbamate reaction technology catalyzed by iodine and iron trifluoride, which effectively introduced dithiocarbamate fragments on imidazo heterocycles (Chinese patent, patent number: ZL201510524047. 2), but this technique is not suitable for the reaction of 5-aminopyrazole and indole
At present, the technical method of introducing dithiocarbamate fragments on indole adopts the reaction of non-commercialized and difficult-to-obtain expensive reagent indole magnesium reagent with thiuram, and this technical scheme is difficult to realize industrial production (Synlett, 2005 ,2691-2693)

Method used

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  • A class of dithiocarbamate compound and its preparation method and application
  • A class of dithiocarbamate compound and its preparation method and application
  • A class of dithiocarbamate compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1. Synthesis of 5-amino-1-methyl-1H-pyrazol-4-yl-dimethylamino-dithiocarbamate (I-1).

[0049] The synthetic route is:

[0050]

[0051] Specifically include the following steps:

[0052] The compound of formula (1a), compound of formula (2a), potassium persulfate, and potassium iodide were mixed in a molar ratio of 1:1.5:2:0.2, wherein the compound of formula (a) was 2 mmol. The reaction system was stirred at 60°C for 12 hours. Cool after the reaction, add an appropriate amount of dichloromethane, extract with water, dry the organic phase, filter with suction, evaporate the filtrate, remove the solvent, and use silica gel column chromatography for the residue, rinse with petroleum ether, detect by TLC, and combine the effluent containing the product , the solvent was distilled off by a rotary evaporator, and the target product was obtained as a white solid by vacuum drying, with a yield of 61% and a purity of 99.5% (HPLC).

[0053] Compound I-1 physical c...

Embodiment 2

[0059] Example 2. Synthesis of 5-amino-1-methyl-3-phenyl-1H-pyrazol-4-yl-dimethylamino-dithiocarbamate (I-8).

[0060] The synthetic route is:

[0061]

[0062] Specifically include the following steps:

[0063] The above formula (1h) compound, formula (2a) compound, potassium persulfate, and potassium iodide were used in a molar ratio of 1:1.5:2:0.2, wherein the formula (1h) compound was 2 mmol. The reaction system was stirred at 60°C for 12 hours. Cool after the reaction, add an appropriate amount of dichloromethane, extract with water, dry the organic phase, filter with suction, evaporate the filtrate, remove the solvent, and use silica gel column chromatography for the residue, rinse with petroleum ether, detect by TLC, and combine the effluent containing the product , the solvent was distilled off by a rotary evaporator, and the target product was obtained as a white solid by vacuum drying, with a yield of 87% and a purity of 99.3% (HPLC).

[0064] Compound I-8 phys...

Embodiment 3

[0070] Example 3. Synthesis of 2-methyl-1H-indol-3-yl-dimethylamino-dithiocarbamate (II-2).

[0071]

[0072] Specifically include the following steps:

[0073] The above formula (3a) compound, formula (2a) compound, potassium persulfate, and potassium iodide were used in a molar ratio of 1:1.5:2:0.2, wherein the formula (3a) compound was 2 mmol. The reaction system was stirred at 60°C for 12 hours. Cool after the reaction, add an appropriate amount of dichloromethane, extract with water, dry the organic phase, filter with suction, evaporate the filtrate, remove the solvent, and use silica gel column chromatography for the residue, rinse with petroleum ether, detect by TLC, and combine the effluent containing the product , the solvent was distilled off by a rotary evaporator, and the target product was obtained as a white solid by vacuum drying, with a yield of 94% and a purity of 99.6% (HPLC).

[0074] Compound II-2 physical constants and characterization data are as fol...

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Abstract

The invention discloses a class of dithiocarbamate compounds, a preparation method and application thereof. The dithiocarbamate compounds of the present invention include 5-aminopyrazole-dithiocarbamate, indole-dithiocarbamate, and substituted benzene-dithiocarbamate. In the present invention, under the presence of an oxidizing agent and an iodine reagent, the aromatic hydrocarbon 5-aminopyrazole compounds, indole compounds or substituted benzene compounds and aminodithioformyl disulfide compounds are reacted in a reaction solvent respectively, thereby Dithiocarbamate compounds of formula I, formula II and formula III are obtained. The compound has different antibacterial activities against rose anthracnose, Fusarium oxysporum, Fusarium laminarum, Fusarium solani, Geotrichum candidum, Penicillium digitatum, Penicillium italicum or rice blast fungus.

Description

technical field [0001] The invention belongs to the field of chemical biology research, and in particular relates to a class of dithiocarbamate compounds and a preparation method and application thereof. Background technique [0002] Carbamate pesticides have the advantages of strong selectivity, wide insecticidal spectrum, synergists can be used to improve drug efficacy, low toxicity to humans, animals and fish, simple structure and easy synthesis. Dithiocarbamate compounds have been proved to have excellent biological activity. A large number of studies have shown that the splicing of dithiocarbamate fragments and nitrogen heterocycles has excellent biological activity ("Research Progress in Biological Activity of Carbadithiocarbamate Compounds", Applied Chemistry, 2015, 32(2), 123 -133), has obvious antitumor, antibacterial, antioxidative and insecticidal and other biological activities. In drug development, nitrogen-containing heterocycles including pyrazole, indole, p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/46C07D209/30C07D471/06C07D455/04C07C333/20A01N47/18A01N47/22A01P3/00
CPCA01N47/18A01N47/22C07C333/20C07D209/30C07D231/46C07D455/04C07D471/06
Inventor 汤日元黄卓斌张晓勇
Owner SOUTH CHINA AGRI UNIV