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Poly-substituted pyridino-[4,3d] pyramine with antibacterial and herbicide activity and its production thereof

A technology of pyridine and pyrimidine, which is applied in the field of a class of multi-substituted pyrido[4,3-d]pyrimidines with fungicidal and herbicidal activity and its preparation, which can solve the problem of few research reports on pesticide activity

Inactive Publication Date: 2006-03-15
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Early studies on pyrido[4,3-d]pyrimidine compounds with pesticide activity were all focused on fungicides, insecticides, herbicides, etc. ] The research on the biological activity of pyrimidine skeleton compounds mainly focuses on the pharmacological activity, but there are few reports on its pesticide activity.

Method used

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  • Poly-substituted pyridino-[4,3d] pyramine with antibacterial and herbicide activity and its production thereof
  • Poly-substituted pyridino-[4,3d] pyramine with antibacterial and herbicide activity and its production thereof
  • Poly-substituted pyridino-[4,3d] pyramine with antibacterial and herbicide activity and its production thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] The preparation of embodiment 1 compound 1

[0017] Preparation of 3-n-propyl-5-methyl-4-methylene-7-methylthio-3,4-dihydro-pyrido[4,3-d]pyrimidine-8-carbonitrile

[0018]

[0019] 15mmol of 2-methyl-3-acetyl-5-cyano-6-methylthio-4-pyridinamine was added to a 50ml reaction flask, dissolved in 20ml of dichloromethane, and 15mmol of triethyl orthoformate was added, The reaction was carried out at 0°C for 25 hours. After the reaction was complete, the unreacted triethyl orthoformate and the solvent were distilled off under reduced pressure. The residue was chromatographed under reduced pressure to obtain white crystal pyridine ether amidine with a melting point of 16.5-16°C and a yield of 65.6%. MS (m / z, %): 277 (M + , 63.21), 199 (31.34), 183 (22.45), 152 (27.81), 77 (100).

[0020] Add 2mmol 2-methyl-3-acetyl-5-cyano-6-methylthiopyridine-4-imine methylene ethyl ether and 15ml absolute ethanol to a 50ml reaction flask, add 3mmol Propylamine was stirred and reacted a...

Embodiment 2

[0067] Preparation of compound 3

[0068] Preparation of 3-allyl-5-methyl-4-methylene-7-methylthio-3,4-dihydro-pyridin[4,3-d]pyrimidine-8-carbonitrile

[0069]

[0070] Add 15mmol of 2-methyl-3-acetyl-5-cyano-6-methylthio-4-pyridinamine into a 50ml reaction flask, dissolve it in 20ml of chloroform, add 20mmol of triethyl orthoformate, The reaction was carried out at 20°C for 20 hours. After the reaction was complete, the unreacted triethyl orthoformate and the solvent were distilled off under reduced pressure, and the residue was chromatographed under reduced pressure to obtain a white crystal of pyridine ether amidine.

[0071] Add 2mmol 2-methyl-3-acetyl-5-cyano-6-methylthiopyridine-4-imine methylene ethyl ether and 15ml of anhydrous methanol into a 50ml reaction flask, add equimolar Allylamine was heated to 60°C for 8 hours to react, and a white solid was precipitated, which was filtered and recrystallized with methanol solvent to obtain a white solid with a yield of 72...

Embodiment 3

[0117] Preparation of Compound 11

[0118] 3-(2,4-Dichlorophenoxyacetylamino)-5-methyl-4-methylene-7-methylthio-3,4-dihydro-pyrido[4,3-d]pyrimidine- 8-Nitrile

[0119]

[0120] Add 15mmol 2-methyl-3-acetyl-5-cyano-6-methylthio-4-pyridinamine into a 50ml reaction flask, add 15mmol triethyl orthoformate, and react at 120°C for 10 hours, After the reaction was complete, the solvent was precipitated under reduced pressure, and the residue was subjected to column chromatography under reduced pressure to obtain white crystal pyridine ether amidine.

[0121] Add 2mmol 2-methyl-3-acetyl-5-cyano-6-methylthiopyridine-4-imine methylene ethyl ether and 15ml anhydrous dioxane into a 50ml reaction flask, Quickly add 6 mmol of 2,4-dichlorophenoxyacetylhydrazide, heat to 100°C and react for 6 hours. After the solid precipitates, it is recrystallized with DMF. The pure product obtained is a white solid with a yield of 71%. m.p.205~207℃

[0122] C 19 h 15 Cl 2 N 5 o 2 S:

[0123] E...

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Abstract

A multiple substituted pyrido(4,3-d) pyrimidine with bactericidal and herbicidal activity and its production are disclosed. In structural formula, R is alkyl or substituted alkyl or alkenyl or alkyl, heterocyclic substituted alkyl, fused heterocycle substituted alkyl, hydroxy-alkyl, phenyl alkyl or substituted phenyl alkyl, substituted or non-substituted phenoxy-acetylamino or phenoxy-propionamido. It can be used as inhibitor and bactericide for cotton wilt mould, rice stripe virus, or cucumber mildew or wheat mildew.

Description

technical field [0001] The present invention relates to 3-substituted alkyl-5-methyl-4-methylene-7-methylthio-3,4-dihydro-pyrido[4,3-d]pyrimidines having fungicidal and herbicidal activity - Preparation of 8-carbonitrile and its intermediates, and its biological activity as fungicide and herbicide. Background technique [0002] Pyrido[4,3-d]pyrimidine compounds are a class of heterocyclic compounds that have been studied very popular at home and abroad in recent years. This type of compound has both medicinal activity and pesticide activity, especially in medical research, it has shown a wide range of physiological and pharmacological activities, and can be used to treat various types of tumors, cancer, leukemia, AIDS and many neurological diseases. In addition, it can also be used It is used in health care such as pain relief, anti-inflammation, and anti-allergy. [0003] Early studies on pyrido[4,3-d]pyrimidine compounds with pesticide activity were all focused on fungic...

Claims

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Application Information

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IPC IPC(8): C07D471/06A01N43/90A61P13/00
Inventor 贺红武王涛廖桂红莫文妍任青云
Owner HUAZHONG NORMAL UNIV
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