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Application of 2-aryl substituted pyrrole compound in drug for killing bulinus

A compound and aryl technology, applied in the field of schistosomiasis prevention and control, can solve the problems of fish loss, toxicity, and high toxicity

Active Publication Date: 2019-01-11
JIANGSU INST OF PARASITIC DISEASES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The molluscicides used in the past, such as sodium pentachlorophenate, have disadvantages such as large doses, reduced molluscicidal effect under sunlight exposure, adsorption on soil and organic matter, loss from water, and toxicity to fish. There was an accident of poisoning and death among applicators. At the same time, sodium pentachlorophenate has teratogenic, carcinogenic, and mutagenic effects. The drug has been banned from being used on-site mollusc control
Niclosamide has low toxicity to humans and animals and no irritation to the skin, but is highly toxic to fish and can cause a large number of fish to die under the effective molluscicide concentration
Bromoacetamide has strong molluscicidal effect, low toxicity to fish, easily soluble in water, and convenient to use, but it is easy to deliquescence, unstable when exposed to heat, acid and alkali, and can also cause dermatitis, etc.
The solubility of nicotinamide in water is low, and there is a phenomenon of small bubble snails climbing up when dipping and killing, and the killing effect on snail eggs is poor, and it is expensive and has a small output, so the large-scale application is limited to a certain extent.
Other chemical molluscicides include quicklime, trichlorfon, 666, urea, and naphthalene, but they have not been widely used due to their high toxicity or strong irritation to human skin.

Method used

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  • Application of 2-aryl substituted pyrrole compound in drug for killing bulinus
  • Application of 2-aryl substituted pyrrole compound in drug for killing bulinus
  • Application of 2-aryl substituted pyrrole compound in drug for killing bulinus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Synthesis of compound 5

[0067]

[0068] (1) Synthesis of Triisopropylpyrrole

[0069] Measure 200mLTHF into a 1000mL three-neck flask, cool down to 0°C, slowly add 12.0g (0.500mol) sodium hydride, stir for 10min, add 17.0g (0.253mol) pyrrole dropwise to the suspension, and stir at 0°C for 1.5h , then slowly dropwise added 13.7g (0.259mol) triisopropylchlorosilane, after the addition was completed, stirred for 2h, added ice water, extracted with ethyl acetate, the extract was dried over anhydrous sodium sulfate, suction filtered and concentrated to obtain 51.7 g oil.

[0070] (2) Synthesis of 3-formaldehyde-1-H pyrrole

[0071] Preparation of Vilsmeier reagent: Weigh 3.9 g (0.876 mol) of DMF in a three-neck flask, cool down to 0°C, then weigh 89.6 g (0.584 mol) of phosphorus oxychloride and slowly add it dropwise to DMF. Stir at ℃ for 1.5h.

[0072] Measure an appropriate amount of dichloromethane to completely dissolve the prepared Vilsmeier reagent, cool down ...

Embodiment 2

[0078] Synthesis of compound 7

[0079]

[0080] (1) Synthesis of 2-phenylaziridine:

[0081] Dissolve 10.4g (100mmol) of styrene in 80mL of carbon tetrachloride, dissolve 16g (200mmol) of liquid bromine in 60mL of carbon tetrachloride, keep the styrene solution at 15-20°C in an ice-water bath, and slowly dissolve the liquid bromine solution Add it dropwise into the styrene solution, stir for 2 hours, wash with water, dry, and rotary evaporate under reduced pressure to obtain a white solid (1).

[0082] Dissolve the white solid (1) in 140 mL DMSO, add 9.8 g (150 mmol) sodium azide under nitrogen protection, and stir overnight at room temperature. Then 4 mL of an aqueous solution containing 4 g of sodium hydroxide was added to the mixture, and stirring was continued for 24 h. The reaction product was poured into 400mL of 2% (wt%) sodium bicarbonate solution, extracted with dichloromethane, the organic layer was washed repeatedly with water, dried and then rotary evaporated...

Embodiment 3

[0087] Synthesis of Compound 12

[0088]

[0089] Firstly, α-p-chlorophenylglycine was N-formylated with a mixture of formic acid and acetic anhydride, converted to the corresponding N-formyl derivative, and further reacted with 2-chloroacrylonitrile in the presence of acetic anhydride for 1 ,3-dipolar addition reaction to generate the corresponding N-formyl derivatives; further 1,3-dipolar addition reaction with 2-chloroacrylonitrile in the presence of acetic anhydride to generate arylpyrrolenitrile 12 As the main product, the total yield of the two-step reaction is 73.6%, and the product is light yellow solid powder with a melting point of 161-162°C; 1 H NMRδ(in acetone-D 6 ):6.59(t, J=2.7Hz, 1H), 7.05(t, J=2.8Hz, 1H), 7.55(d, J=8.5Hz, 2H, Ar-H), 7.84(d, J=8.3Hz , 2H, Ar-H), 11.30 (bs, 1H, N-H).

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Abstract

The invention relates to an application of a 2-aryl substituted pyrrole compound in a drug for killing bulinus, and belongs to the technical field of schistosomiasis control. The invention particularly provides a chemical structure and preparation method of the 2-aryl substituted pyrrole compound. A molluscicide is prepared with the 2-aryl substituted pyrrole compound as the active ingredient. Themolluscicide has a form of suspension agent, emulsion or microemulsion, and is applied to kill bulinus. When the 2-aryl substituted pyrrole compound is used as the active ingredient of the molluscicide, the application amount for soaking killing is 0.5 mg / L-10.00 mg / L, and the soaking killing time is 24 h-72 h. Experiments prove that the 2-aryl substituted pyrrole compound has the killing activity against bulinus, has the toxicity to aquatic organisms lower than that of conventional snail-killing drug niclosamide, and can be made into the molluscicide applied in the field of schistosomiasis control.

Description

technical field [0001] The invention relates to the application of a 2-aryl-substituted pyrrole compound in the preparation of a snail-killing drug, belonging to the technical field of schistosomiasis prevention and control. Background technique [0002] Schistosoma, also known as Schistosoma, belongs to the flatworm phylum, mainly referring to all 19 species of the same genus classified under the genus Schistosoma. Among them, there are 6 species that can parasitize humans. There are three main species, which are prevalent in the Middle East, Asia and South America. They have a wide distribution and are the main three types of schistosomiasis that can infect humans; , Mekong River Basin, because most of them are zoophilic strains, the impact on humans is small. The growth process of schistosomiasis must go through the parasitic stage in freshwater snails before it can infect other hosts. After schistosomiasis parasitizes, it usually chooses to settle in the veins and blood...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/36A01N43/78A01N43/50A01P7/04
CPCA01N43/36A01N43/50A01N43/78
Inventor 邢云天戴建荣
Owner JIANGSU INST OF PARASITIC DISEASES
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