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Sanguinarine alcoholate and chelerythrine alcoholate and preparation method and application thereof in animal acaricidal drugs

A technology of chelerythrine and alcoholate, applied in the directions of botanical equipment and methods, application, acaricide, etc., can solve the problems of frequent recurrence and repeated infection, bad, etc., and achieve low residual drug resistance and mite eradication. The effect of strong activity and good therapeutic effect

Inactive Publication Date: 2014-04-09
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But at present, abamectin class acaricides are facing serious problems in three aspects: one, like all chemical drugs, along with the long-term use of abamectin class drugs, more and more mites have produced With the increasingly serious drug resistance, the recurrence and superinfection of acariasis are becoming more and more frequent; secondly, the adverse environmental and ecological impacts caused by abamectins due to their broad-spectrum, high-efficiency, and stable characteristics have aroused strong concern. Residual drugs in animal excrement can seriously affect the decomposition process of many normal microorganisms and protozoa; third, abamectin drugs can only drive and kill insects, but are ineffective against eggs. Only repeated medication can improve the rate of deworming rate, prevent the recurrence of mite

Method used

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  • Sanguinarine alcoholate and chelerythrine alcoholate and preparation method and application thereof in animal acaricidal drugs
  • Sanguinarine alcoholate and chelerythrine alcoholate and preparation method and application thereof in animal acaricidal drugs
  • Sanguinarine alcoholate and chelerythrine alcoholate and preparation method and application thereof in animal acaricidal drugs

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preparation example Construction

[0036] 1. The preparation method of sanguinarine alcoholate:

[0037] Add 1.00 mmol of sanguinarine and 50 mL of methanol, ethanol, propanol, or isopropanol into a 100 mL round-bottom flask, heat until the solids are completely dissolved; then add dropwise 0.5 mol / L of the corresponding alcohol sodium alkoxide, namely methanol Sodium, sodium ethoxide, sodium propoxide or sodium isopropoxide solution 4.0 mL, stirred at room temperature for 30 minutes, evaporated the solvent to dryness under reduced pressure; dissolved the residue with 50 mL chloroform, filtered off the insoluble matter, and evaporated the filtrate to remove the solvent under reduced pressure to dryness; the resulting residue was recrystallized with the corresponding alcohol, namely methanol, ethanol, propanol or isopropanol, to obtain white crystals or solids, namely sanguinarine alcoholate, with a yield of 85% to 95%.

[0038] 2. The preparation method of chelerythrine alcoholate:

[0039] Add 1.00 mmol of ch...

Embodiment 1

[0043] 6-Methoxydihydrosanginarine, referred to as sanguinarine methanolate, the molecular structure is that R in the structure of sanguinarine alcoholate is replaced by a methyl group: light pink prism (methanol), mp 194-194.5℃. 13 C NMR (125 MHz, CD 3 OD) δ : 104.6(C-1), 148.1(C-2), 147.4(C-3), 100.6(C-4), 126.9(C-4a), 138.2(C-4b), 85.9(C-6), 108.8(C-6a), 145.3(C-7), 147.2(C-8), 113.2(C-9), 116.4(C-10), 125.8(C-10a), 122.8(C-10b), 120.1 (C-11), 123.7(C-12), 131.1(C-12a), 101.1(2,3-OCH 2 O), 101.7(7,8-OCH 2 O), 40.9(N-Me), 54.1(6-OMe). 1 H NMR (CDOD 3 , TMS) δ : 7.76(1H, d, J 8.6 Hz, H-11), 7.69(1H, s, H-4), 7.48(1H, d, J8.6 Hz, H-12), 7.20(1H, d, J 8.2 Hz, H-10), 7.12(1H, s, H-1), 6.93(1H, d, J 8.2 Hz, H-9), 6.11(2H, s, OCH 2 O), 6.04(2H, s, OCH 2 O), 5.37(1H, s, H-6), 3.46(3H, s, OCH 3 ), 2.79(3H, s, NCH 3 ); ESI-MS (positive mode) m / z : 364[M+H] + .

Embodiment 2

[0045] 6-Ethoxydihydrosanguinarine, referred to as sanguinarine alcoholate, the molecular structure is that R in the structure of sanguinarine alcoholate is replaced by ethyl: white prism (ethanol), mp 210-212℃. 13 C NMR (125 MHz, CD 3 OD) δ : 104.6(C-1), 148.0(C-2), 147.4(C-3), 100.7(C-4), 126.9(C-4a), 138.5(C-4b), 84.2(C-6), 108.7(C-6a), 145.2(C-7), 147.3(C-8), 113.4(C-9), 116.4(C-10), 125.8(C-10a), 122.9(C-10b), 120.3 (C-11), 123.6(C-12), 131.0(C-12a), 101.0(2,3-OCH 2 O), 101.7(7,8-OCH 2 O), 40.9(N-Me), 61.6(O C h 2 CH 3 ), 15.0 (OCH 2 C h 3 ). 1 H NMR (CDOD 3 , TMS) δ : 7.76(1H, d, J 8.6 Hz, H-11), 7.66(1H, s, H-4), 7.48(1H, d, J 8.6 Hz, H-12), 7.40(1H, d, J 8.2 Hz, H-10), 7.12(1H, s, H-1), 6.92(1H, d, J 8.2 Hz, H-9), 6.11(2H, s, OCH 2 O), 6.08(2H, s, OCH 2 O), 5.48(1H, s, H-6), 3.90-3.93(1H, m, OC H 2 CH 3 ), 3.65(1H, q, J 7.0 Hz, OC H 2 CH 3 ), 2.76(3H, s, NCH 3 ), 1.08(3H, t, J 7.0 Hz, OCH 2 C H 3 ); ESI-MS (positive mode) m / z : 378...

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Abstract

The invention relates to a sanguinarine alcoholate and a chelerythrine alcoholate and a preparation method and application thereof in acaricidal drugs for animals. Livestock and poultry acariasis is an in vitro parasitic disease which can cause serious damage to the animal health, and serious stress response of animals to influence ingestion, feed efficiency and weight gain, even cause death. At present, the control of the animal acariasis mainly relies on drugs for killing ticks and mites, and the ticks and mites can produce resistance to the drugs after the drugs are used for a long time, so that the drugs can cause adverse environmental and ecological effects, and can only drive and kill polypides instead of ova. The sanguinarine alcoholate and the chelerythrine alcoholate are derived from natural compounds-sanguinarine and chelerythrine alcoholate, and exist in the form of free alkaloids in the acaricidal drugs for animals. The sanguinarine alcoholate and the chelerythrine alcoholate have the characteristics of low toxicity, low residue and not easy production of resistance to the drugs of natural drugs, and have remarkable acaricidal activity and good treatment effect on the acariasis of animals when the sanguinarine alcoholate and the chelerythrine alcoholate are applied as the acaricidal drugs for animals.

Description

technical field [0001] The invention relates to sanguinarine alcoholate and chelerythrine alcoholate, a preparation method thereof and an application in animal acaricide. Background technique [0002] Livestock and poultry acariasis is a kind of ectoparasitic disease that is ubiquitous and seriously endangers the health of animals. It is characterized by contact infection, severe itching and severe skin inflammation. It can cause severe stress reactions in animals and affect animal feeding and sleep. , feed efficiency and animal weight gain, severe cases can cause animal death. The occurrence of animal mites is very common and quite stubborn. Pigs, sheep, cattle, chickens, rabbits, dogs, foxes, mice, etc. are all infected with mites and the incidence is very high. Therefore, the disease seriously affects the production performance of animals and the quality of livestock products. In addition, mites also play an intermediary role in the spread of bacterial and viral disease...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/056C07D491/153A01N43/90A01P7/02
Inventor 周乐郑峰孙艺芳张琦苗芳
Owner NORTHWEST A & F UNIV
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