2,3,4,7-polysubstituted naphthyridine [4,3-d] pyrimidine derivates with sterilization activity and preparation thereof

A multi-substitution, pyridine technology, applied in the direction of biocides, chemicals for biological control, biocides, etc., can solve the problem of few research reports on pesticide activity

Inactive Publication Date: 2008-12-17
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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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  • 2,3,4,7-polysubstituted naphthyridine [4,3-d] pyrimidine derivates with sterilization activity and preparation thereof
  • 2,3,4,7-polysubstituted naphthyridine [4,3-d] pyrimidine derivates with sterilization activity and preparation thereof
  • 2,3,4,7-polysubstituted naphthyridine [4,3-d] pyrimidine derivates with sterilization activity and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Compound 1

[0035] 3-O-fluorobenzyl-5-methyl-4-methylene-7-methylthio-3,4-dihydropyrido[4,3-d]pyrimidine-8-carbonitrile

[0036]

[0037] 15 mmoles of 2-methyl-3-acetyl-5-cyano-6-methylthio-4-pyridinamine were added to a 50-ml reaction flask, and 15 mmoles of triethyl orthoformate were added, at 100 After the reaction was completed, the unreacted triethyl orthoformate and the solvent were distilled off under reduced pressure, and 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).

[0038] Add 2 mmoles of 2-methyl-3-acetyl-5-cyano-6-methylthiopyridine-4-iminomethylidene ethyl ether, 15 mL of dichloromethane into a 50 mL reaction flask , adding 3 millimoles of o-fluorobenzylamine, stirring and reacting at 20°C for 12 hours, a white solid was precipitated, filtered, recrystallized ...

Embodiment 2

[0100] Compound 8

[0101] 3-Ethyl-5-methyl-4-methylene-7-methoxy-3,4-dihydropyrido[4,3-d]pyrimidine-8-carbonitrile

[0102]

[0103] Add 15 mmoles of 2-methyl-3-acetyl-5-cyano-6-methoxy-4-pyridinamine into a 50 ml reaction flask, add 60 mmoles of triethyl orthoformate, add the catalyst Acetic anhydride was measured and reacted at 130°C for 12 hours. After the reaction was complete, the unreacted triethyl orthoformate was distilled off under reduced pressure, and the residue was chromatographed under reduced pressure to obtain a yellowish crystal of pyridine ether amidine.

[0104] Add 1 mmol of 2-methyl-3-acetyl-5-cyano-6-methoxypyridine-4-iminomethylene ethyl ether, 15 mL of anhydrous DMF into a 50 mL reaction flask , adding 2 mmoles of ethylamine aqueous solution, heated to 120 ° C for 1 hour, a white solid was precipitated, filtered, recrystallized from a mixed solvent of acetone and petroleum ether, and the obtained pure product was a white solid with a yield of 68%. ...

Embodiment 3

[0139] Compound 9

[0140] 3-n-propyl-5-methyl-4-methylene-7-methoxy-3,4-dihydropyrido[4,3-d]pyrimidine-8-carbonitrile

[0141]

[0142] Add 15 mmoles of 2-methyl-3-acetyl-5-cyano-6-methoxy-4-pyridinamine into a 50 ml reaction flask, add 60 mmoles of triethyl orthoformate, add the catalyst P-toluenesulfonic acid was measured and reacted at 130°C for 12 hours. After the reaction was complete, the unreacted triethyl orthoformate was distilled off under reduced pressure, and the residue was chromatographed under reduced pressure to obtain a light yellow crystal of pyridine ether amidine.

[0143] Add 1 mmole of 2-methyl-3-acetyl-5-cyano-6-methoxypyridine-4-imine methylene ethyl ether, 15 ml of anhydrous dioxane to 50 ml of Add 2 mmoles of n-propylamine to the reaction flask, heat to 100° C. for 6 hours to react, a solid is precipitated, filtered, recrystallized in a mixed solvent of acetone and petroleum ether, and the obtained pure product is a yellow solid with a yield of 6...

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Abstract

The invention provides a polysubstituted pyrido (4, 3-d) pyrimidine compounds with bactericidal activity and a synthesis method thereof. The structural general formula of polysubstituted pyrido (4, 3-d) pyrimidine compounds of the invention is showed in general formula I which includes three compounds as showed in general formulas I-1, I-2 and I-3; the proposed structure of general formula I-1 is the development and complement of Patent CN 100335481C while no relevant coverage on the structure of the general formulas I-2 and I-3 is released currently. The experiments indicate that the compounds with the general formula I can obviously inhibit various pathogenic bacteria such as fusarium oxysporum vasinfectum, rhizoctonia solani, botrytis cinera pers, gibberella saubinetii, ring rot of apple, cotton anthracnose, cucumber timberrot, cucumber target leaf spot, scab of cucumber, pepper phytophthora blight, etc., and can be used as the active ingredient of bactericides.

Description

technical field [0001] The present invention relates to the preparation of 2,3,4,7-multi-substituted pyrido[4,3-d]pyrimidine derivatives with fungicidal activity and their intermediates, as well as their biological activity as a fungicide. 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. 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P3/00
Inventor 贺红武莫文妍任青云
Owner HUAZHONG NORMAL UNIV
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