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5-methyl-1,2,3-thiadiazole-1,3,4-oxadiazole derivatives, and preparation method and application thereof

A technology of thiadiazole and oxadiazole, applied in the field of 5-methyl-1

Inactive Publication Date: 2014-12-31
JIANGXI JIAYIN PHOTOELECTRIC MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 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-1,3,4-oxadiazole derivatives, and preparation method and application thereof
  • 5-methyl-1,2,3-thiadiazole-1,3,4-oxadiazole derivatives, and preparation method and application thereof
  • 5-methyl-1,2,3-thiadiazole-1,3,4-oxadiazole derivatives, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis and structure identification of intermediate 5-methyl-1,2,3-thiadiazole-4-bishydrazide compound III:

[0032] In a 50 milliliter round bottom flask, add 3.15 millimoles of 5-methyl-1,2,3-thiadiazole-4-formylhydrazide, 6.3 millimoles of substituted benzoic acid, 6.3 millimoles of phosphorus pentachloride, 10 milliliters of benzene was heated to reflux for 3 hours. After the reaction was monitored by thin-layer chromatography, the reaction system was poured into ice water, and the pH value was adjusted to 7.0 with sodium bicarbonate, and extracted 3 times with ethyl acetate (20 milliliters × 3 ), the combined organic layers were dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain compound III, then recrystallized with ethanol, calculated the yield with the pure product obtained, measured the melting point and 1 H NMR, the amount of synthetic compound III is enlarged or reduced according to the corresponding rat...

Embodiment 2

[0034] Synthesis and structure identification of 5-methyl-1,2,3-thiadiazole bi-1,3,4-oxadiazole derivative IV:

[0035] method one:

[0036] Add 6.3 mmoles of 5-methyl-1,2,3-thiadiazole-4-carboxylhydrazide, 6.3 mmoles of substituted benzoic acid, and 10 ml of phosphorus oxychloride into a 50 ml round bottom flask, and heat to reflux for 6 hours , after the completion of the reaction monitored by thin-layer chromatography, the reaction system was poured into ice water, the pH ester was adjusted to 7.0 with sodium carbonate, and then extracted 3 times with ethyl acetate (20ml×3), the organic layers were combined, and washed with anhydrous sulfuric acid The sodium was dried, the solvent was distilled off under reduced pressure, and the residue was separated by column chromatography with an eluent volume ratio of sherwood oil: ethyl acetate 2: 1 to obtain compound IV. Calculate the yield with the resulting pure product, measure the melting point and 1 H NMR, the amount of synthe...

Embodiment 3

[0040] The antibacterial or bactericidal activity of 5-methyl-1,2,3-thiadiazole 1,3-4-oxadiazole derivative IV of the present invention:

[0041] The names and codes of the common phytopathogenic 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: Physalosporapiricola; PS: Pelicularia sasakii; RC: Cereal silk Rhizoctonia cerealis; SS: Sclerotinia sclerotiorum, these strains are very representative and can represent most of the pathogenic bacteria species that occur in the field in agricultural production. The results of the bacterial growth rate method are shown in Table 2, and Table 2 shows that at 50 micrograms per milliliter, all compounds synthesized by the present invention have different degrees of bactericidal activity, TN-OXZ2, TN-OXZ4, TN-OXZ6, TN- The bactericidal activity of OXZ7 and TN-OXZ9 to CA was higher than 40%; th...

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Abstract

The invention provides 5-methyl-1,2,3-thiadiazole-1,3,4-oxadiazole derivatives, and a preparation method and application thereof. The invention relates to heterocyclic compounds containing 1,2,3-thiadiazole and having chemical structural formula IV. The invention discloses the structural general formula, and a synthetic method of the compounds and the application of the compounds for being used as bactericide, plant anti-viral agent and plant activator. The derivatives can be applied for preparing the bactericide, plant anti-viral agent and plant activator in combination with agriculturally acceptable adjuvant or synergist, and the invention also discloses application of the compounds in combination with commercial insecticide, bactericide, plant anti-viral agent and plant activator for treating and controlling diseases, pests and viruses in agriculture, forestry, and gardening industries, and the preparation method.

Description

technical field [0001] The technical scheme of the present invention relates to 1,2-oxadiazole-containing compounds, in particular to 5-methyl-1,2,3-thiadiazole-1,3-4-oxadiazole derivatives. Background technique [0002] In the past 20 years, heterocyclic compounds have been the mainstream of new pesticide development. The introduction of heterocyclic compounds can not only improve their biological activity, but also change their selectivity. Among heterocyclic compounds, new pesticides with high biological activity have appeared, making pesticides towards Developing in the direction of ultra-efficient and pollution-free (Wu Ying. Journal of Yueyang Vocational and Technical College. 2011, 26(5): 67-71). Nitrogen-containing heterocyclic compounds have unique biological activity, low toxicity, and high systemic property. They are often used as structural units of medicines and pesticides, and play an important role in the synthesis of medicines and pesticides (Xiao Guomin, et ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C07D285/06A01N43/828A01P3/00A01P1/00A01P21/00
Inventor 范志金特蒂安娜·卡林丽娜毛武涛华学文王盾姬晓恬莫则林·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 JIANGXI JIAYIN PHOTOELECTRIC MATERIAL
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