Cytisine derivatives and their preparation and application in pesticides

A technology of cytisine and its derivatives, which is applied in the field of natural medicinal chemistry, can solve the problems of underived synthesis of cytisine, structure-activity relationship research, etc., and achieve high product purity, simple synthesis process, and good poisonous activity Effect

Active Publication Date: 2019-11-12
GAUNGXI TIANYUAN BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many reports on the medicinal activity of cytisine in recent years, there are relatively few studies on the application of cytisine compounds as pesticides in the control of plant diseases and insect pests at home and abroad, and the research is only found in cytisine analogues Preliminary determination of insecticidal activity against radish aphids (Pesticide Biochemistry and Physiology 65,1–5(1999)), no systematic derivation and synthesis of cytisine, structure-activity relationship research, especially for the control of armyworm And the application of the medicine of Chilo borer has not yet been reported in the literature

Method used

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  • Cytisine derivatives and their preparation and application in pesticides
  • Cytisine derivatives and their preparation and application in pesticides
  • Cytisine derivatives and their preparation and application in pesticides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of N-2-naphthylsulfonyl-cytisine (1)

[0030] Its concrete synthetic operation is as follows:

[0031] With cytisine as reactant, triethylamine as catalyst, carry out sulfonylation reaction with 2-naphthalenesulfonyl chloride in organic solvent dichloromethane, wherein the moles of cytisine, 2-naphthalenesulfonyl chloride and catalyst The ratio is 5:10:15, and the amount of organic solvent added is 80 times the molar number of cytisine to obtain the cytisine derivative; Alkali derivative crude product, then the cytisine derivative crude product is separated by silica gel column chromatography with a volume ratio of 30:1:1 chloroform and methanol elution system to obtain high-purity N-2-naphthylsulfonyl - Cytisine.

[0032]

[0033] The detection data of the product are as follows: white solid, yield: 86%; 1 H NMR (400MHz, CDCl 3 )δ8.23(d,J=1.8Hz,1H),8.00–7.84(m,3H),7.71–7.58(m,2H),7.49(dd,J=8.6,1.9Hz,1H),7.15(dd ,J=9.1,6.7Hz,1H),6.36(d,J=9.1Hz,1H),5.94...

Embodiment 2

[0035] Synthesis of N-methylsulfonyl-cytisine (2)

[0036]Taking cytisine as reactant, taking triethylamine as catalyzer, carrying out sulfonylation reaction with methylsulfonyl chloride in organic solvent benzene, wherein the mol ratio of cytisine, methylsulfonyl chloride and catalyzer is 5: 10:20, the amount of organic solvent added is 85 times the molar number of cytisine, and cytisine derivatives can be obtained; after the sulfonylation reaction is completed, the crude product of cytisine derivatives is obtained after vacuum distillation , and then the crude product of cytisine derivatives is separated by silica gel column chromatography with the elution system of chloroform and methanol at a volume ratio of 30:2:1 to obtain high-purity N-methylsulfonyl-cytisine.

[0037]

[0038] The product detection data is as follows: white solid, yield: 88%; 1 H NMR (400MHz, CDCl 3 )δ7.41–7.25(m,1H),6.47(dd,J=9.1,1.4Hz,1H),6.07(dd,J=6.9,1.4Hz,1H),4.15(d,J=15.7Hz,1H ),3.98–3.82(m...

Embodiment 3

[0040] Synthesis of N-dimethylsulfonyl-cytisine (3)

[0041] With cytisine as reactant and triethylamine as catalyst, carry out sulfonylation reaction with dimethylaminosulfonyl chloride in organic solvent tetrahydrofuran, wherein the moles of cytisine, dimethylaminosulfonyl chloride and catalyst The ratio is 5:10:25, and the addition amount of organic solvent is 85 times of cytisine molar number, can obtain cytisine derivative; Base derivative crude product, then carry out silica gel column chromatography separation to the cytisine derivative crude product with the chloroform and methanol elution system of volume ratio 30:3:1 and can obtain high-purity N-dimethylsulfamoyl- Cytisine.

[0042]

[0043] The product detection data is as follows: white solid, yield: 89%; 1 H NMR (400MHz, CDCl 3 )δ7.37–7.21(m,1H),6.47(dd,J=9.1,1.4Hz,1H),6.08(dd,J=6.9,1.4Hz,1H),4.14(m,1H),3.90(m ,1H),3.70–3.60(m,1H),3.55(m,1H),3.19–3.04(m,3H),2.62–2.57(m,1H),2.52(s,6H),2.08–2.01(m ,1H),1.96–...

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Abstract

The present invention relates to a novel cytisine derivative and a preparation method thereof and application thereof in pesticides for control of armyworm and Chilo suppressalis. The derivative is obtained by reacting of the cytisine with differently-substituted sulfonyl chloride according to the preparation method. Insecticidal activity tests prove that the derivative has a good control effectson test insects. The preparation process is simple, raw materials are cheap and easy to obtain, and the product has a high purity.

Description

technical field [0001] The invention belongs to the field of natural medicine chemistry and the technical field of biopesticides, discloses a new application of cytisine derivatives, and specifically relates to the application of cytisine derivatives in the preparation of medicines for preventing and controlling armyworm and stem borer. Background technique [0002] At present, the main control methods of plant diseases and insect pests include chemical control, biological control and physical control. Among them, chemical control has the characteristics of good control effect, quick effect, and convenient use. However, due to the widespread use of chemical pesticides, the "3R" problems of residue, resistance and re-emergence are becoming more and more serious, which has aroused great concern from the society. Therefore, the research and development of efficient and safe natural source pesticides to prevent and control plant diseases and insect pests has become an important...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/18A01N43/90A01P7/04
CPCA01N43/90C07D471/18
Inventor 李卫国刘映前杨程杰零春华李俊采陈诚张君香
Owner GAUNGXI TIANYUAN BIOCHEM
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