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N-substituent group-N-(substituted phenylaminocarbonyl)-1-substituted sulfonylthioformylhydrazide derivatives and application thereof

A technology of sulfonylthiocarbohydrazide and anilinoformyl, applied in N-substituent-N-(substituted anilinoformyl)-1-substituted sulfonylthiocarbohydrazide derivatives and their application fields , can solve the problems of increased drug resistance of bacteria, decreased control effect, pesticide residues, etc., and achieve excellent antibacterial activity, simple synthesis method, and good antibacterial activity

Inactive Publication Date: 2019-11-15
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional fungicides (such as eclozole, thiabyl copper, ketal, carbendazim, etc.) have become more and more serious problems such as the increase of bacterial resistance, the decline of control effect, and the residue of pesticides caused by long-term application.

Method used

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  • N-substituent group-N-(substituted phenylaminocarbonyl)-1-substituted sulfonylthioformylhydrazide derivatives and application thereof
  • N-substituent group-N-(substituted phenylaminocarbonyl)-1-substituted sulfonylthioformylhydrazide derivatives and application thereof
  • N-substituent group-N-(substituted phenylaminocarbonyl)-1-substituted sulfonylthioformylhydrazide derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Preparation of N-methyl-N-(phenylcarbamoyl)-1-methylthiocarbohydrazide (compound number a):

[0043] (1) The preparation of methyl anilate intermediate:

[0044] Throw aniline (20g, 0.21mol), potassium carbonate (32.65g, 0.24mol) and dichloromethane (100-150mL) in a 250mL three-necked flask, slowly add methyl chloroformate (24.35g, 0.26mol ) after reaction at room temperature for 3-5h. After stopping the reaction, the reaction system was washed with water, separated, dried, filtered with suction and precipitated under reduced pressure to obtain 28.65 g of methyl anilinate, with a yield of 88.25%.

[0045] (2) Preparation of anilinoformohydrazide intermediate:

[0046] Throw methyl aniline formate (15g, 0.1mol) and 80% hydrazine hydrate (62.09g, 1.0mol) in a 100mL three-necked round-bottomed flask, heat up to reflux for 36 hours, cool in an ice bath to precipitate a white solid, and filter with suction The crude product of aniloformyl hydrazide was obtained...

Embodiment 2

[0051] Example 2: Preparation of N-ethyl-N-(phenylcarbamoyl)-1-ethylthiocarbothiohydrazide (compound number is b)

[0052]Step (1)-(3) is the same as embodiment 1

[0053] (4) Preparation of N-ethyl-N-(phenylcarbamoyl)-1-ethylthiocarbohydrazide:

[0054] Throw N-(anilinoyl) potassium dithioformate (1g, 4.32mmol), potassium carbonate (0.6g, 4.32mmol), potassium iodide (62.55mg, 0.38mmol) and 25mL of water in a 50mL three-neck round-bottomed flask, Stir at room temperature until the solid is completely dissolved, slowly add diethyl sulfate (0.76g, 4.90mmol) dropwise, stir at room temperature (20°C) for 12h to end the reaction, filter the system with suction, wash the filter cake with petroleum ether and recrystallize it with absolute ethanol 0.81 g of white solid was obtained, with a yield of 75.38%;

Embodiment 3

[0055] Example 3: Preparation of N-benzyl-N-(phenylcarbamoyl)-1-benzylthiocarbohydrazide (compound number is c)

[0056] Step (1)-(3) is the same as embodiment 1

[0057] (4) Preparation of N-benzyl-N-(phenylcarbamoyl)-1-benzylthiocarbohydrazide:

[0058] Throw N-(anilinoyl) potassium dithioformate (0.325g, 1.22mmol), potassium carbonate (0.169g, 1.22mmol), potassium iodide (0.022g, 0.135mmol) and 25mL of water in a 50mL three-neck round bottom flask , stirred at room temperature until the solid was completely dissolved, slowly added benzyl chloride (0.31g, 2.45mmol) dropwise, stirred at room temperature (20°C) for 12h to end the reaction, filtered the system with suction, washed the filter cake with petroleum ether and recrystallized with absolute ethanol 0.372g of white solid was obtained, yield 74.54%;

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Abstract

The invention discloses N-substituent group-N-(substituted phenylaminocarbonyl)-1-substituted sulfonylthioformylhydrazide derivatives as well as a preparation method and application thereof. The derivatives have a structural general formula (I) shown in the description, wherein n = 0, 1 or 2, and X = C, N, O or S; R1 is C1-4 alkyl or substituted benzyl; and R2 is a hydrogen atom, an o-position, anm-position, a p-position monosubstituted halogen atom, C1-4 alkyl, C1-2 alkoxy, or a polysubstituted halogen atom. The derivatives provided by the invention have excellent antibacterial activity against bacterial diseases such as xanthomonas oryzae, xanthomonas oryzicola and xanthomonas citri, the synthetic raw materials have low costs, and the synthetic method is simple and easy.

Description

technical field [0001] The present invention relates to the technical field of pesticides, in particular to an N-substituent-N-(substituted anilinoformyl)-1-substituted sulfonylthiocarbohydrazide derivatives, and also relates to the N-substituent -N-(substituted anilinoformyl)-1-substituted sulfonyl thioformohydrazide derivatives, and the N-substituent-N-(substituted anilinoformyl)-1-substituted sulfonyl Antibacterial application of thioformohydrazide derivatives to bacterial diseases such as rice bacterial blight, rice bacterial streak, citrus canker and tobacco R. solanacearum. Background technique [0002] In recent years, plant bacterial diseases have occurred on a large scale and tend to spread further. However, traditional fungicides (such as eclozole, thiabactin, carbendazole, carbendazim, etc.) have become more and more serious problems such as increased bacterial resistance, decreased control efficiency, and pesticide residues due to long-term application. For thi...

Claims

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Application Information

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IPC IPC(8): C07C333/28C07C275/00C07C273/18C07C271/28C07C269/04A01N47/34A01P1/00
CPCA01N47/34C07C269/04C07C273/1836C07C333/28C07C271/28C07C275/00
Inventor 宋宝安张阿伟胡德禹李绍远谢丹丹李洪德王小果
Owner GUIZHOU UNIV
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