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Application of 2,5-bis(substituted carbamoylmethylthio)-1,3,4-thiadiazoles in inhibiting the growth of cyanobacteria

A carbamoylmethylthio and thiadiazole technology, applied in the application of inhibiting the growth of cyanobacteria, in the field of 2,5-di-1,3,4-thiadiazole compounds, which can solve the problem that cyanobacteria cannot grow or even death, etc.

Active Publication Date: 2018-09-07
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Studies have shown that fructose-1,6- / sedoheptulose-1,7-bisphosphatase (cy-FBP / SBPase), which is ubiquitous in cyanobacteria, plays a very important strategic role in the regulation of carbon metabolism in the Calvin cycle of cyanobacteria status, is a potential algicide target, and inhibition or mutation of cyanobacterial fructose-1,6- / sedoheptulose-1,7-bisphosphatase will cause cyanobacteria to fail to grow or even die

Method used

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  • Application of 2,5-bis(substituted carbamoylmethylthio)-1,3,4-thiadiazoles in inhibiting the growth of cyanobacteria
  • Application of 2,5-bis(substituted carbamoylmethylthio)-1,3,4-thiadiazoles in inhibiting the growth of cyanobacteria
  • Application of 2,5-bis(substituted carbamoylmethylthio)-1,3,4-thiadiazoles in inhibiting the growth of cyanobacteria

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preparation example Construction

[0021] The preparation method of the compound shown in formula I comprises the following steps: (1) reacting 2,5-dimercapto-1,3,4-thiadiazole and sodium chloroacetate under alkaline conditions, then acidifying to obtain the reaction intermediate (compound shown in formula II); (2) intermediates and anilines (compound shown in formula III, R 1 , R 2 , R 3 , R 4 , R 5 Same as above) react under the protection of dehydrating agent DCC and argon (Ar), and the corresponding target product can be obtained after post-treatment. The reaction formula of step (1) and (2) is as follows:

[0022]

[0023] The reaction in step (2) above uses DCC as a dehydrating agent, and the by-product N,N'-dicyclohexylurea can be removed after the reaction solution is poured into water, and the target product can be precipitated. Suction filtration and ethanol recrystallization gave pure product.

Embodiment 1

[0025] Preparation of compound I-12,5-bis(p-iodophenylcarbamoylmethylthio)-1,3,4-thiadiazole

[0026]

[0027] (1) Dissolve 20mmol of 2,5-dimercapto-1,3,4-thiadiazole into 8.0mL of 20% sodium hydroxide solution, add 37.8mL of 30% sodium chloroacetate solution dropwise under stirring, and control the pH The value is between 10 and 11, and the reaction is 6h. Concentrated hydrochloric acid was acidified to pH = 2, and a large amount of white precipitate was obtained. Suction filtration, washing with water, drying, recrystallization with ethanol, drying again to obtain pure compound II.

[0028] (2) Add 1.5 mmol of compound II and 3.3 mmol of p-iodoaniline into 3.0 mL of anhydrous DMF, protect with argon, and cool to 0-5° C. in an ice-water bath. Dissolve 0.31g of DCC in 1.0mL of anhydrous DMF, then add the DCC solution to the above mixture, and complete the addition within 3 minutes. Stir at room temperature for 2h and let stand overnight. After filtration, the filtrate w...

Embodiment 2

[0136] The 2,5-bis(substituted carbamoylmethylthio)-1,3,4-thiadiazole compounds prepared in Example 1 were subjected to cyanobacterial fructose-1,6- / sedoheptulose-1,7 - Bisphosphatase inhibition test. Cyanobacterial fructose-1,6- / sedum heptulose-1,7-bisphosphatase hydrolyzes fructose-1,6-bisphosphate into fructose-6-phosphate and inorganic phosphate. Therefore, the activity of cyanobacterial fructose-1,6- / sedum heptulose-1,7-bisphosphatase can be determined by measuring the increase of inorganic phosphate, and then reflect the above-mentioned 2,5-bis(substituted carbamoyl methyl Sulfuryl)-1,3,4-thiadiazole compounds as inhibitors of inhibitory efficiency. The specific operation is as follows:

[0137] (1) Weigh the compound in advance, dissolve it in DMSO, and prepare the above-mentioned 2,5-di(substituted carbamoylmethylthio) with different concentrations of 0, 0.01, 0.03, 0.1, 0.3, 1, 3, 10, 30mM, etc. -1,3,4-thiadiazole compounds.

[0138](2) The reaction system for mea...

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Abstract

The invention discloses application of a 2,5-di(substituted formamyl methylthio group)-1,3,4-thiadiazole compound in inhibiting blue-green algae growth, and belongs to the field of agricultural production and environmental protection. The structure of the 2,5-di(substituted formamyl methylthio group)-1,3,4-thiadiazole compound is as shown in a formula I, and R1, R2, R3, R4 and R5 in the formula I each adopt any one radical group of hydrogen or a halogen or an alkyl group or a hydroxyl group or trifluoromethyl or a nitro group. The compound has a good inhibiting effect on blue-green algae fructose-1,6- / sedoheptulose-1,7-biphosphatase; a good inhibiting effect on blue-green algae is achieved, and the compound can serve as the effective component of algicide to be applied to comprehensive treatment of blue-green algae bloom. The compound can be mixed with an allowable carrier in a water body or a diluent to be prepared into various commonly-used dosage forms such as a water mixture, an emulsion, an aqueous solution and a mobile agent to serve as the algicide for use. Please see the formula I in the description.

Description

technical field [0001] The invention relates to the fields of agricultural production and environmental protection, in particular to the application of 2,5-bis(substituted carbamoylmethylthio)-1,3,4-thiadiazole compounds in inhibiting the growth of cyanobacteria. Background technique [0002] In recent years, there have been large-scale outbreaks of cyanobacteria blooms in various places. The algae damage directly affects the domestic and industrial water in the surrounding areas, seriously damages the ecological environment, brings huge economic losses to fishery production and tourism development, and also poses a threat to public health. Great hidden danger. The use of chemical algicides has the advantages of economy, high efficiency, convenience, and quick effect. It has always been an indispensable and important part of the comprehensive management system of algae hazards, especially during the period of large-scale outbreaks of cyanobacteria blooms. The most important...

Claims

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Application Information

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IPC IPC(8): A01N43/824A01P13/00C07D285/125
Inventor 冯玲玲万坚秦玉昌韩强赵晓晶李俊冯江涛
Owner HUAZHONG NORMAL UNIV
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