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Triazolothiadiazole compounds and preparation method and application thereof

A technology of thiadiazoles and thiadiazole derivatives, applied in the field of heterocyclic compounds, can solve the problems of few research reports and the like

Inactive Publication Date: 2010-08-11
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since Kanaoka fused triazole and thiadiazole in one molecule to produce s-triazolo[3,4-b]-1,2,4-thiadiazole heterocyclic compound (Kanaoka.J.Pharm.Soc .Jpn., 1956,76,1133), patent (Cai, Sui Xiong, et al., US2008113984) and literature (S.Nanjunda Swamy, Basappa, B.S.Priya, et al.European Journal of Medicinal Chemistry, 2006, 41: 531-538; Dejiang Li, Xiucheng Bi and Heqing Fu. Phosphorus, Sulfur, and Silicon, 2007, 182: 1307-1314; Prakash Karegoudar et al., Eur.J. Med. Chem, 2008, 43, 808-815.) A wide range of biological activities of such fused heterocyclic compounds containing aliphatic chains and aryl substitutions have also been reported, such as: anti-inflammatory activity, anti-tumor activity, insecticidal activity, bactericidal activity, bactericidal activity, herbicidal activity, etc., considering furan, thiophene Heterocyclic compounds such as , pyridine and pyrazole, thiadiazole and isoxazole also have a wide range of biological activities, and there are not many research reports on such compounds containing these heterocyclic substituents

Method used

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  • Triazolothiadiazole compounds and preparation method and application thereof
  • Triazolothiadiazole compounds and preparation method and application thereof
  • Triazolothiadiazole compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation and structure identification of compound 3-(4-methyl-1,2,3-thiadiazol-5-yl)-4-amino-5-mercapto-1,2,4-s-triazole

[0044] Add 6.25 grams (0.1 moles) of 80% hydrazine hydrate to 50 milliliters of absolute ethanol, and slowly add 17.2 grams (0.1 moles) of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid dropwise under stirring Ethyl ester, stirring vigorously after dropping, for about 15 minutes, a large amount of solids precipitated instantly, filtered with suction and washed with absolute ethanol, spin-dried the filtrate to obtain a yellow solid, washed with petroleum ether, combined the solids, dried under infrared light, and obtained orange-yellow 4- Methyl-1,2,3-thiadiazole-5-carboxylhydrazide 14.9 grams, yield rate 94.2%; 11.6 grams (0.07 mole) 4-methyl-1,2,3-thiadiazole-5 -Formylhydrazide was added into 150 ml of absolute ethanol solution with 7.5 g (0.11 moles) of 82% KOH, stirred to dissolve it, and then added dropwise with CS 2 8.36 g (0.11 mol), gradual...

Embodiment 2

[0046] Compound YZK-a: 3-phenyl-6-(4-methyl-1,2,3-thiadiazol-5-yl)-triazolo-[3,4-b]-1,3,4 -Synthesis and structure identification of thiadiazole

[0047] Add 1.5 mmol 3-phenyl-4-amino-5-mercapto-1,2,4-s-triazole and 1.5 mmol 4-methyl-1,2,3-thiadiazole-5-carboxylic acid to 25 ml round bottom flask, add 10 ml POCl 3 , magnetic stirring, oil bath heating to maintain the temperature of 110-120 degrees, reflux for 5 hours, the reaction is complete, under ice water cooling, slowly add ice water dropwise, a large amount of solids precipitate, stand overnight, suction filter, and use saturated NaHCO 3 The product was washed with solution, then washed with water until neutral, and dried to obtain a crude product with a yield of 87%. 2 h 5 OH recrystallization to get green needle-like crystals; melting point: 173-175 degrees, 1 HNMR (δ, DMSO-d 6 ): 7.563-8.246 (m, 5H, ArH), 3.003 (s, 3H, thiadiazolyl-CH 3 ).

Embodiment 3

[0049] Compound YZK-b: 3-phenyl-6-(5-methyl-1,2,3-thiadiazol-5-yl)-triazolo-[3,4-b]-1,3,4 -Synthesis and structure identification of thiadiazole

[0050] Add 1.0 mmol 3-phenyl-4-amino-5-mercapto-1,2,4-s-triazole and 1.0 mmol 5-methyl-1,2,3-thiadiazole-4-carboxylic acid to In a 25 ml round bottom flask, add 10 ml POCl3, stir with a magnet, heat in an oil bath to keep the temperature at 110-120 degrees, and reflux for 5 hours. overnight, filter with suction, and wash with saturated NaHCO 3 The product was washed with solution, then washed with water until neutral, and dried to obtain a crude product with a yield of 60%. 2 h 5 OH recrystallization to obtain off-white powder crystals; melting point: 236-239 degrees, 1 H NMR (δ, DMSO-d 6 ): 7.573-8.297 (m, 5H, ArH), 3.062 (s, 3H, thiadiazolyl-CH 3 ).

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Abstract

The invention provides triazolothiadiazole containing derivatives, a synthesizing method thereof and application thereof. The invention relates to 1,2-diazole containing heterocyclic compounds, which have the following chemical structural general formula. The invention discloses a chemical structure and a synthesizing method of the compounds, a using method and application of the triazolothiadiazole containing derivatives for resisting TMV viruses, a using method and application in inhibiting the growth of plant pathogenic fungi, and application of the combination of the compounds, the conventional commercial anti-virus medicaments and bactericides, herbicide and insecticide in preventing and controlling diseases, pests, weeds and virus diseases of the agriculture, forestry and gardening.

Description

technical field [0001] The technical scheme of the present invention relates to heterocyclic compounds containing 1,2-oxadiazole, in particular to triazolothiadiazole derivatives. Background technique [0002] Thiadiazole heterocyclic compounds have a wide range of biological activities, such as anti-inflammatory, anthelmintic, weed control, plant growth regulation, etc. (BoschelliD.H.et al., J.Med.Chem.1993,36,1802; Saad H., Indian J.Chem, 1996, 35B, 980; Bakulev V A, Dehaen W.The Chemistry of 1,2,3-thiadiazole, 2004, John Wiley & Sons, Inc.), the inventor's previous research also found that thiadiazole Derivatives have very good activity of inducing plant resistance to viral diseases and fungal diseases (Fan Zhijin, etc., National Invention Patent of the People's Republic of China, publication number: CN1810808A; Fan Zhijin, etc., National Invention Patent of the People's Republic of China, Publication Number: CN2020667A), wherein , Methianamide is a low-toxic compound, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04A01N43/90A01P1/00A01P3/00A01P7/04A01P7/02A01P5/00A01P13/00A01P21/00
Inventor 范志金杨知昆米娜张海科马琳左翔郑琴香
Owner NANKAI UNIV
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