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Halogenated pyrazole sophocarpidine derivatives with insecticidal activity as well as preparation method and application thereof

A technology of halogenated pyrazole matrine and substituted pyrazole matrine, which is applied in the field of halogenated pyrazole matrine derivatives and its preparation, can solve the problems of limiting the clinical application of matrine, and achieve a large-scale Production, wide application prospect, effect of high insecticidal activity

Active Publication Date: 2020-06-09
ZHONGKAI UNIV OF AGRI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Matrine has the advantages of a wide range of drug sources and a safe use process, but it only shows moderate activity, and it also has certain toxicity to the central nervous system, which limits the clinical application and further promotion of matrine

Method used

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  • Halogenated pyrazole sophocarpidine derivatives with insecticidal activity as well as preparation method and application thereof
  • Halogenated pyrazole sophocarpidine derivatives with insecticidal activity as well as preparation method and application thereof
  • Halogenated pyrazole sophocarpidine derivatives with insecticidal activity as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] In addition, these halogenated pyrazole matrine derivatives of the present invention can be used alone as the only active insecticidal ingredients, or used in combination with other active insecticidal ingredients to make commercial preparations. The concentration of the active compound in the use forms made from commercial formulations can vary within wide ranges. The concentration of active compound in the dosage form used may be from 0.0000001% to 99% by weight of active compound, preferably between 0.0001% and 1%. Embodiment 1 prepares 4-fluoropyrazole matrine

[0050] 1. Synthesis steps

[0051] After assembling the experimental synthesis device, add 0.175g of sophocarpine, 0.5g of 4-fluoropyrazole, 0.06g of tripotassium phosphate, and 5mL of 1,4-dioxane into a 50mL three-neck flask, condense and reflux, and put the oil bath The temperature was set to 90°C and the speed of the stirrer was adjusted. During the reaction, the color of the system gradually deepened. ...

Embodiment 2

[0060] Embodiment 2 prepares 4-chloropyrazole matrine

[0061] 1. Synthesis steps

[0062] After assembling the experimental synthesis device, add 1.23g of sophocarpine, 0.5g of 4-fluoropyrazole, 0.5g of tripotassium phosphate, and 5mL of DMSO into a 50mL three-neck flask, condense and reflux, set the temperature of the oil bath to 90°C and adjust The speed of the stirrer, the color of the system gradually deepened during the reaction, and the reaction was sampled every 1h for TLC detection. After the reaction was found to be basically complete, the reaction was stopped, and the final reaction time was 4.5h. Separation and purification were carried out with an eluent with a distribution ratio of ethyl acetate:ethanol=10:1 (volume ratio), and the fractions containing the target product were collected and concentrated by rotary evaporation to obtain 4-chloropyrazole matrine.

[0063] 2. Structural characterization

[0064] (1) Infrared IR analysis

[0065] like image 3 As s...

Embodiment 3

[0075] Embodiment 3 prepares 4-bromopyrazole matrine

[0076] 1. Synthesis steps

[0077] After assembling the experimental synthesis device, add 0.5 g of sophocarpine, 0.3 g of 4-bromopyrazole, 0.06 g of cesium carbonate, and 5 mL of 1,4-dioxane into a 50 mL three-neck flask, condense and reflux, and lower the temperature of the oil bath to Set it to 90°C and adjust the speed of the stirrer. During the reaction, the color of the system gradually deepened. Samples were taken every 1 hour for TLC detection. It was found that the reaction was basically completed and the reaction was stopped. The final reaction time was 7 hours. After cooling down slightly, 10 mL of dichloromethane was added to dissolve, filtered and concentrated by rotary evaporation to obtain a crude product. Separation and purification were carried out with an eluent whose distribution ratio was ethyl acetate:ethanol=10:1 (volume ratio), and the fractions containing the target product were collected and conce...

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Abstract

The invention discloses halogenated pyrazole sophocarpidine derivatives with insecticidal activity as well as a preparation method and an application thereof. The invention provides a halogenated pyrazole sophocarpidine derivative which is a compound shown as a formula (I), and in the formula, R is halogen; wherein the substitution site of R is 3, 4 or 5 substitution on a pyrazole ring or a combination thereof. The sophocarpidine compound and halogenated pyrazole are subjected to a chemical reaction and conversion in a water phase and weak base catalytic system to obtain the halogenated pyrazole sophocarpidine derivative which is high in insecticidal activity, simple and convenient in preparation method and low in cost. The death rate of plutella xylostella reaches 100% after 0.5 g / mL of 4-iodopyrazole sophocarpidine is used for 72 h, and the halogenated pyrazole sophocarpidine derivative has a wide application prospect in the field of agriculture, and especially has a good applicationprospect in the aspect of lepidoptera pest control.

Description

technical field [0001] The invention belongs to the technical field of biomedicine. More specifically, it relates to a class of halogenated pyrazole matrine derivatives with insecticidal activity, its preparation method and application. Background technique [0002] Modifying the structure of natural products, improving drug activity and improving drug defects is a feasible way to develop new drugs. Matrine is a clinical drug with anti-inflammatory, analgesic and anti-tumor effects, and it is also a botanical pesticide with broad-spectrum anti-insect activity. [0003] Sophora flavescens is one of the traditional medicines with a long history in my country, and it is grown in Shanxi and Hubei. Matrine is mainly used in clinical medicine, but less in agriculture. The molecular structure of matrine is relatively simple, and it has good transformability. It is expected to synthesize and screen highly toxic target compounds, and provide candidate compounds for the ultimate cr...

Claims

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Application Information

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IPC IPC(8): C07D471/22A01N43/90A01P7/04
CPCA01N43/90C07D471/22
Inventor 程杏安蒋旭红何慧清东方云张汉辉刘展眉谭醇灿朱明月
Owner ZHONGKAI UNIV OF AGRI & ENG
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