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Salifying method of 2-(1-amido-ethyl)-N-phenyl thiazole-4-methanamide compound and application

A technology of phenylthiazole and compound is applied in the field of 2-(1-amino-ethyl)-N-phenylthiazole-4-carboxamide compound salt formation and application, and achieves low non-target biological toxicity and synthesis method simple effect

Active Publication Date: 2014-06-11
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Based on the previous work of our research group, considering that the final application of algicides is in aquatic ecosystems, (2-(1-Amino-ethyl)-N-phenylthiazole-4-carboxamides can also be salt-formed No report

Method used

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  • Salifying method of 2-(1-amido-ethyl)-N-phenyl thiazole-4-methanamide compound and application
  • Salifying method of 2-(1-amido-ethyl)-N-phenyl thiazole-4-methanamide compound and application
  • Salifying method of 2-(1-amido-ethyl)-N-phenyl thiazole-4-methanamide compound and application

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Embodiment 1

[0030] The systematic name of compound M-2 (2-(1-amino-ethyl)-N-(4-bromo-phenyl)-thiazole-4-carboxamide (English: 2-(1-aminoethyl)-N- (4-bromophenyl)thiazole-4-carboxamide, and make it into hydrochloride as follows:

[0031]

[0032] The preparation method of S-1 into hydrochloride: Accurately weigh 1 mmol of the series of derivatives in a 50ml round bottom flask and add 25ml of absolute ethanol to fully dissolve, and build a hydrochloric acid generating device: weigh about 30g of anhydrous NaCl and place it in a three-necked flask In, and gradually add concentrated sulfuric acid to it dropwise, after hydrochloric acid gas is gradually generated, the hydrochloric acid gas is dried and then introduced into the ethanol solution, and crystals are gradually precipitated until saturation. The solvent was spin-dried to obtain a solid.

[0033] When R1-R4 are different substituents, the series of hydrochlorides S-1~S-5 synthesized are as follows

[0034] Table 3 several derivati...

Embodiment 2

[0040]

[0041] Accurately weigh 1 mmol of the series of derivatives in a 50 ml round bottom flask and add 25 ml of absolute ethanol to fully dissolve it to build a hydrochloric acid generating device: add 1.2 mmol of oxalic acid to it, and gradually crystallize until it is saturated. The solvent was spin-dried to obtain a solid.

[0042] Table 5X is the derivatives of different organic acid salts

[0043]

[0044]

[0045] The series of salts Y-1 to Y-8 synthesized when X is substituted with different organic acid salts, the biological activity assay data on Scenedesmus obliques, Chlorella pyrenoidosa, and Microcystis aeruginosa are as follows:

[0046] The biological activity testing method is the same as that of the above-mentioned M series derivatives, and will not be described in detail here.

[0047] Table 6 The activity determination EC of different organic acid salt compounds on three kinds of algae 50 (mg / L)

[0048]

[0049] The experimental results sh...

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Abstract

The invention relates to a salting method of a 2-(1-amido-ethyl)-N-phenyl thiazole-4-methanamide compound and a derivative thereof, and application thereof in the aspects of prevention and treatment of limnetic algae. The 2-(1-amido-ethyl)-N-phenyl thiazole-4-methanamide compound is a compound shown in a structural general formula, wherein X is HCl, H2SO4, H3PO4, maleic acid, fumaric acid, para-toluenesulfonic acid, citric acid, oxalic acid, malic acid, acetic acid, tartaric acid and the like; R, R1, R2 and R3 are H, halogens, C2-C5 alkyls, sulfo groups, alkoxy, nitryl, amino, substituted amino and the like. The salifying method of the compound is simple and convenient in process, and applicable to industrial production, and has the potential of developing an efficient algicide. The 2-(1-amido-ethyl)-N-phenyl thiazole-4-methanamide compound has excellent broad-spectrum killing algae activity on limnetic algae chlorophyta verdigris microcystin algae, scenedesmus obliquus, chlorella pyrenoidosa and the like. Compared with the traditional algicide, the 2-(1-amido-ethyl)-N-phenyl thiazole-4-methanamide compound has the characteristics of being high in activity, friendly to environment, low in toxicity on non-target organisms and the like, simple in synthetic method, and is an algicide lead compound with value.

Description

technical field [0001] The invention relates to a salt-forming method of 2-(1-amino-ethyl)-N-phenylthiazole-4-carboxamide compound and its application in killing algal blooms. Background technique: [0002] Bacillamide4 was isolated from a thermophilic actinomycete (Thermoactinomyces strain TM-64) as early as 1976. Regrettably, due to the small amount of isolated compounds, their biological activities have not been paid attention to and studied for a long time. Our research group realized the total synthesis of Bacillamide4 for the first time. By optimizing the structure of Bacillamide4, we discovered a class of promising algicidal active compounds (Xie Longguan, Xu Xiaohua, Wei Zhigang and other thiazole compounds in freshwater algae killing algae. Chinese invention patent CN201210112982 .4). [0003] It is a new trend to use allelopathic natural products as lead compounds to develop new pesticide products. Compared with traditional inorganic copper ion algicides, natura...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/56A01N43/78A01P13/00
CPCA01N43/78C07D277/56
Inventor 徐效华刘奇声陶园园谢龙观
Owner NANKAI UNIV
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