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Halogenated nitrogen-containing heterocyclic matrine derivative as well as preparation method and application thereof

A nitrogen heterocycle and matrine technology is applied in the field of halogenated nitrogen-containing heterocycle matrine derivatives and their preparation, which can solve the problems of slow drug effect, low activity, low bioavailability and the like, and achieve fast drug effect , High bioavailability, good poisoning effect

Pending Publication Date: 2021-06-11
ZHONGKAI UNIV OF AGRI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to overcome the defects or deficiencies of existing matrine insecticides such as low activity, slow drug effect and low bioavailability, and provide a halogenated nitrogen-containing heterocyclic matrine derivative

Method used

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  • Halogenated nitrogen-containing heterocyclic matrine derivative as well as preparation method and application thereof
  • Halogenated nitrogen-containing heterocyclic matrine derivative as well as preparation method and application thereof
  • Halogenated nitrogen-containing heterocyclic matrine derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～7

[0064] This example provides a series of halogenated chiocyclic alkali derivatives, structural formulas as follows:

[0065]

[0066] Among them, MAT is a bitter base, 3-Cl-Pyr-MAT is 3-chloropyrazole alcoholica, 3-Br-Pyr-Mat is 3-bromipatezole, 3-I-Pyr-Mat is 3-iodopyrazole, 4-F-IND-MAT is 4-fluoronone bitter, 5-Cl-Ind-MAT is 5-chloroanne bitter, 5-Br-Ind-Mat For 5-bromohae borne, 5-Br-IND-MAT is 5-bromoblane alcoholic.

[0067] The above derivatives were prepared by the following procedure: dissolved the raguase and the halogenic heterocyclic lysate in 4.0 ml of organic solvent (ethanol, methanol, dioxane, acetonitrile, petroleum ether, etc.), via 0.03 g of Catalyst (cesium fluoride, cesium carbonate, tripassate, tetramethoxysilane, etc.), 2-10 h at a certain temperature (60-140 ° C), then subtracted analysis, eluent is acetate Esters, ethanol, methanol, and acetonitrile or the like are eluted in a certain volume ratio. Finally, the split segment obtained was detected by TLC, ...

Embodiment 1

[0069] Example 1, 3-Cl-Pyr-Mat spectrum data:

[0070] SELECTED IR DATA (KBR Disk, CM -1 : v (C-H, C = C) 3114w; V (C = O) 1627S; V (C-BR) 755m. 1 H NMR (700MHz, CDCL 3 δ: 1.35-1.77 (m, 8h), 1.96 (D, J = 11.4 Hz, 2H), 2.60 (DT, J = 6.3, 13.1 Hz, 2H,), 2.78 (DT, J = 11.8, 21.7 Hz, 4H), 2.88 (D, J = 5.4 Hz, 2H), 3.05 (DD, J = 3.9, 12.8 Hz, 1H), 3.84 (D, J = 5.9 Hz, 2H), 4.34 (DT, J = 5.1, 12.7 Hz, 1H), 4.64 (Tt, J = 3.1, 9.1 Hz, 1H), 6.27 (T, J = 2.4 Hz, 1H), 7.32 (D, J = 2.5 Hz, 1H). 13 C NMR (176MHz, CDCL 3 δ: 20.42, 20.94, 26.44, 27.52, 31.09, 35.49, 37.15, 41.85, 42.11, 50.0, 53.37 (2C), 57.01, 63.57, 108.61, 125.84, 129.22, 165.52.LRMS (ESI) m / z: Calcd 392.12 , Observed 393.6 [M + H] + .

[0071] Figure 1 ~ 5 The infrared spectrum of 3-Cl-Pyr-Mat, mass spectrum spectrum, hydrogen spectrum, carbon spectrum and crystal structure and cell chart. Its crystallographic data and structural analysis parameters are shown in Table 1.

[0072] Table 1 3-Cl-Pyr-MAT crystallographic data...

Embodiment 2

[0075] Example 2, 3-br-Pyr-Mat spectrum data:

[0076] SELECTED IR DATA (KBR Disk, CM -1 : υ (C-H, C = C) 3109W; V (C = O) 1622S; V (C-I) 759m. 1 H NMR (700MHz, CDCL 3 δ: 1.36-1.62 (m, 4H), 1.65-1.78 (m, 4H), 1.86-1.98 (m, 2H), 2.60 (DDT, J = 5.8, 8.3, 14.0 Hz, 1H), 2.74-2.81 (m, 4H), 2.88 (D, J = 1.8 Hz, 2H), 3.05 (T, J = 12.6Hz, 1H), 3.83 (Q, J = 5.4 Hz, 2H,) 4.33 (TD, J = 4.5, 12.7 Hz, 1H), 4.70 (TT, J = 3.0, 8.7 Hz, 1 H), 6.41 (T, J = 2.4 Hz, 1H), 7.26 (D, J = 2.4 Hz 1h). 13 C NMR (176MHz, CDCL 3 Δ: 20.76, 21.28, 26.79, 27.87, 31.53, 35.43, 37.55, 42.20, 42.43, 50.55, 53.62 (2C), 57.36, 63.90, 95.93.17, 129.55, 165.93.LRMS (ESI) m / z: Calcd 440.11 , Observed 441.4 [M + H] + .

[0077] Figure 6 ~ 10 The infrared spectrum of 3-Br-Pyr-Mat, mass spectrum spectrum, hydrogen spectrum, carbon spectrum and crystal structure and cell chart. Its crystallographic data and its structural analysis parameters are shown in Table 2.

[0078] Table 2 3-Br-Pyr-Mat crystallographic data and st...

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Abstract

The invention discloses a halogenated nitrogen-containing heterocyclic matrine derivative as well as a preparation method and application thereof. The derivative has a structural formula as shown in a formula (I) shown in the specification, wherein R1 is halogenated pyrazolyl or halogenated indolyl. The novel halogenated nitrogen-containing heterocyclic ring matrine derivative is obtained by introducing halogenated indolyl and halogenated pyrazolylto modify matrine analogue sophocarpine, and the halogenated nitrogen-containing heterocyclic ring matrine derivative has better inhibitory activity and poisoning effect on spodoptera frugiperda, and is quick in efficacy and high in bioavailability; and an important theoretical foundation is laid for subsequent development of efficient and environment-friendly matrine type grassland spodoptera frugiperda prevention and control insecticides.

Description

Technical field [0001] The present invention relates to the field of pesticide techniques, and Background technique [0002] In recent years, the SpoDoptera FrugiperDa has caused great harm to food security in multiple countries. Moreover, the current grass-shaped larvae has a significant resistance to a variety of organophosphorus, nicotine, and osme ester and urethane, and urethane, and is also resistant to partial transgenic corn. This brings great difficulty to prevention and control. [0003] Researchers have begun to explore the development of biological pesticides to find biological pesticides from the active ingredients to prevent control of grassland gregarime moths because bio-pesticides are not resistant to resistance. Related studies have found that natural compounds such as plant essential oils and sewerpene compounds and their derivatives have certain inhibitory effects on grassland greed, such as methyl flavonoids have an impact on the development and metabolism of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/22A01N43/90A01P7/04
CPCC07D471/22A01N43/90
Inventor 程杏安蒋旭红何慧清张汉辉东方云刘欣李俊杰周子健李俊铭
Owner ZHONGKAI UNIV OF AGRI & ENG
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