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Salt-forming method and application of 2-(1-amino-ethyl)-n-phenylthiazole-4-carboxamide compound
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A technology of phenylthiazole and compound, applied in the field of salt formation and application of 2-(1-amino-ethyl)-N-phenylthiazole-4-carboxamide compound, achieving non-target biological toxicity and low synthetic method simple effect
Active Publication Date: 2016-04-06
NANKAI UNIV
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[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
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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] Preparation method of S-1 into hydrochloride: Accurately weigh 1 mmol of series derivatives in a 50ml round bottom flask and add 25ml of absolute ethanol to fully dissolve, build a hydrochloric acid generating device: weigh about 30g of anhydrous NaCl and place it in a three-necked flask and gradually add concentrated sulfuric acid dropwise to it to gradually generate hydrochloric acid gas, then introduce the hydrochloric acid gas into the ethanol solution after drying, and gradually crystallize out until it is saturated. 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 derivatives hydrochloride
[0035]
...
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 measurement 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 resu...
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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 (ThermoactinomycesstrainTM-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, natural ...
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