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5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives and their preparation method and use

A thiadiazole derivative, thiadiazole technology, applied in the field containing 1

Inactive Publication Date: 2012-12-12
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

1,2,3-Thiadiazole compounds also have a wide range of biological activities. For related patents and literature summaries, see Bakulev, et al.Newyork: John Wiley&Sons, Inc, 2004 monograph. 1,3,4-thiadiazole derivatives, 1,2,5-thiadiazole derivatives and 1,2,4-thiadiazole derivatives, and for 1,2,3-thiadiazole derivatives There are relatively few reports on the activity of

Method used

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  • 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives and their preparation method and use
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  • 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives and their preparation method and use

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Experimental program
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Effect test

Embodiment 1

[0027] Preparation of intermediate N-(2-(5-methyl-1,2,3-thiadiazole-4-carboxhydrazino)thioacyl) substituted benzamide III:

[0028] Add 3.33 millimoles of 5-methyl-1,2,3-thiadiazole-4-carboxamide I, 3.33 millimoles of substituted thioisocyanate II and 20 milliliters of DMF into a 50 milliliter three-necked round bottom flask, Room temperature; stir for 6 hours. A white solid appears. The filtered solid ethanol is recrystallized with a yield of 60%-90%. The melting point and 1 H NMR, the chemical structure and physical and chemical parameters of compound III are shown in Table 1.

Embodiment 2

[0030] Preparation of 5-methyl-1,2,3-thiadiazole and -1,3-4-thiadiazole IV:

[0031] Add 3.0 mmoles of N-(2-(5-methyl-1,2,3-thiadiazole-4-carboxhydrazino)thioacyl) substituted benzamide III into a 50 ml in-situ flask. 20 methanol, 0.1 ml concentrated sulfuric acid, stir and reflux for 6 hours. A white solid appears. The filtered solid ethanol is recrystallized with a yield of 60%-90%. The melting point and 1 H NMR, the chemical structure and physical and chemical parameters of compound IV are shown in Table 1.

Embodiment 3

[0033] The antibacterial or bactericidal activity of the 5-methyl-1,2,3-thiadiazole-linked-1,3-4-thiadiazole derivative IV and its intermediate III of the present invention:

[0034] The names and codes of common plant pathogenic fungi tested in the present invention include AS: Alternaria solani; BC: Botrytis cinerea; CA: Cercospora arachidicola; GZ: Wheat red Gibberella zeae; PI: Phytophthora infestans (Mont.) de Bary; PP: Physalospora piricola; PS: Pellicularia sasakii; RC: Gramineae Rhizoctonia cerealis (Rhizoctonia cerealis); SS: Sclerotinia sclerotiorum (Sclerotinia sclerotiorum), these strains are very representative and can represent most of the pathogen species that occur in the field in agricultural production. The measurement results of the bacterial growth rate method are shown in Table 2. Table 2 shows that at 50 μg / ml, all the compounds synthesized in the present invention have different degrees of bactericidal activity, and the bactericidal activity of TN-TDZ9 and ...

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Abstract

The invention provides 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives and their preparation method and use. The 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives are 1,2,3-thiadiazole-containing heterocyclic compounds. Intermediates of the 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives and the 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives respectively have a general structural formula III and a general structural formula IV. The invention discloses the general structural formula and the preparation method of the 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives, and also discloses a use of the 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives as bactericides, plant virus resistance agents and plant activators. After being mixing with agriculture acceptable assistants or synergists, the 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives can be used for preparation of bactericides, plant virus resistance agents and plant activators. The invention also discloses a use of the 5-methyl-1,2,3-thiadiazole-containing 1,3,4-thiadiazole derivatives combined with commercial insecticides, bactericides, plant virus resistance agents and plant activators in prevention and treatment on agricultural, forest and gardening diseases, insect pests and viral diseases, and also discloses a preparation method thereof.

Description

Technical field [0001] The technical scheme of the present invention relates to compounds containing 1,2-diazole, and specifically relates to 5-methyl-1,2,3-thiadiazole and 1,3-4-thiadiazole derivatives. Background technique [0002] 1,3-4-thiadiazole, because the heterocyclic molecule contains both N and S heteroatoms, it can be used as a donor and acceptor to participate in life activities at the same time, so it exhibits a wide range of biological activities (Liu Hanwen, Organic Chemistry, 20012, 32, 1332.), especially in the field of pesticides, for example, some 1,3-4-thiadiazole compounds exhibit good insecticidal, bactericidal, herbicidal and plant growth regulating activities. Biheterocyclic compounds have also become an important research direction in the field of medicine and pesticides. Introducing two or more heterocyclic active centers in the same molecule can more flexibly change the electronic structure characteristics of the sub-molecules, improve the biological ...

Claims

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Application Information

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IPC IPC(8): C07D285/135C07D285/06A01N43/828A01P3/00A01P1/00A01P21/00
Inventor 范志金特蒂安娜·卡林丽娜华学文王盾姬晓恬毛武涛莫则林·余瑞·余瑞维奇贝尔斯卡娅·娜特丽娅·帕沃洛娃巴库勒夫·瓦西里耶·阿勒克什维奇
Owner NANKAI UNIV
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