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Triazolothiadiazole compound and its preparation method and use

A technology of thiadiazoles and thiadiazole derivatives, which is applied in the field of heterocyclic compounds and can solve the problems of insufficient research reports

Inactive Publication Date: 2011-11-30
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 compound and its preparation method and use
  • Triazolothiadiazole compound and its preparation method and use
  • Triazolothiadiazole compound and its preparation method and use

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 g (0.1 mole) of 80% hydrazine hydrate to 50 ml of absolute ethanol, and slowly add 17.2 g (0.1 mole) of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid dropwise with stirring Ethyl ester, after dripping, stir vigorously, 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, and dried under infrared light to obtain an orange-yellow 4- Methyl-1,2,3-thiadiazole-5-carboxhydrazide was 14.9 g, and the yield was 94.2%; 11.6 g (0.07 mol) of 4-methyl-1,2,3-thiadiazole-5 -Formyl hydrazide was added to 7.5 g (0.11 mol) of 82% KOH in 150 ml of absolute ethanol solution, stirred to dissolve, and then CS was added dropwise 2 8.36 g (0.11 mol), an orange-yellow solid gradually precipit...

Embodiment 2

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

[0047] 1.5 mmoles of 3-phenyl-4-amino-5-mercapto-1,2,4-s-triazole and 1.5 mmoles of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid were added to Add 10 ml POCl to a 25 ml round bottom flask 3 , Magnet stirring, oil bath heating to maintain the temperature 110-120 degrees, reflux for 5 hours, the reaction is complete, under ice water cooling, slowly add ice water dropwise, a large amount of solid precipitation, let stand overnight, suction filtration, saturated NaHCO 3 The product was washed with solution, then washed with water to neutrality, and dried to obtain a crude product with a yield of 87%. Use DMF-C 2 H 5 OH is recrystallized to obtain 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)s-triazolo-[3,4-b]-1,3,4 -Synthesis and structure identification of thiadiazole

[0050] 1.0 mmol of 3-phenyl-4-amino-5-mercapto-1,2,4-s-triazole and 1.0 mmol of 5-methyl-1,2,3-thiadiazole-4-carboxylic acid were added to Add 10 ml of POCl3 to a 25 ml round bottom flask, stir with a magnet, heat the oil bath to maintain the temperature at 110-120 degrees, reflux for 5 hours, after the reaction is complete, under ice water cooling, slowly add ice water dropwise, a large amount of solids precipitate out, Set overnight, filter with suction, use saturated NaHCO 3 The product is washed with solution, then washed with water to neutrality, and dried to obtain a crude product with a yield of 60%. Use DMF-C 2 H 5 OH is recrystallized to obtain off-white powdery 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 present invention provides the preparation of a class of derivatives containing triazolothiadiazole and a synthesis method and application thereof. The present invention relates to heterocyclic compounds containing 1,2-oxadiazole, and they have the following general chemical structure: The present invention The chemical structures and synthetic methods of these compounds and the use and use of these triazolothiadiazole derivatives against TMV virus and the use and use of inducing tobacco to resist TMV virus are disclosed, and the insecticidal and inhibitory properties of these compounds are also disclosed. Methods and uses for the growth of phytopathogenic fungi; also disclose the use of these compounds in combination with existing commercial antiviral agents and fungicides, herbicides and insecticides in controlling agricultural, forestry and horticultural pests, weeds and viral diseases.

Description

Technical field [0001] The technical scheme of the present invention relates to a heterocyclic compound containing 1,2-diazole, and specifically to a derivative of triazolothiadiazole. Background technique [0002] Thiadiazole heterocyclic compounds have a wide range of biological activities, such as anti-inflammatory, repellent, weeding, and regulating plant growth (Boschelli D. H. et al., J. Med. Chem. 1993, 36, 1802; Saad H., Indian J. Chem, 1996, 35B, 980; Bakulev VA, Dehaen W. The Chemistry of 1, 2, 3-thiadiazole, 2004, John Wiley & Sons, Inc.), the inventor’s previous study also found that thiadiazole Derivatives have good activity in inducing plants against viral and fungal diseases (Fan Zhijin, etc., National Invention Patent of the People’s Republic of China, Publication No.: CN1810808A; Fan Zhijin, etc., National Invention Patent of the People’s Republic of China, Publication No: CN2020667A), of which , Methioamide is a low-toxic compound, and field trials have confirm...

Claims

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Application Information

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Patent Type & Authority Patents(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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