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1,2,3-thiadiazole-1,3,4-thiadiazole compounds and preparation method and application thereof

A technology of thiadiazole and thiadiazole linkage, applied in 1 field

Inactive Publication Date: 2013-05-08
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

All of the above researches link 1,2,3-thiadiazole or 1,3,4-thiadiazole and amide groups in the same molecule, but it is difficult to combine these three groups in the same molecule at the same time. No literature report

Method used

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  • 1,2,3-thiadiazole-1,3,4-thiadiazole compounds and preparation method and application thereof
  • 1,2,3-thiadiazole-1,3,4-thiadiazole compounds and preparation method and application thereof
  • 1,2,3-thiadiazole-1,3,4-thiadiazole compounds and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Compound WSX-9: Preparation and structure identification of 1-(4-methyl-1,2,3-thiadiazole-5-carbonyl)thiosemicarbazide

[0037] In a 100 mL round bottom flask, add 4-methyl-1,2,3-thiadiazole-5-carboxhydrazide (5 g, 31.6 mmol), concentrated hydrochloric acid (6.8 g), water (30 mL) and dry potassium thiocyanate (4.6 grams, 47.5 mmoles), heated in an oil bath at 90 to 100 degrees Celsius under electromagnetic stirring, and after about 1 hour, a large amount of white solids were precipitated, continued heating for 3 hours, stopped the reaction, and pumped out after cooling filtered, and washed with dilute sodium bicarbonate solution and water respectively, and dried to obtain a pure white solid product with a yield of 85%; melting point: 183-185 degrees Celsius; 1 Determination of HNMR, 1 HNMR (solvent: DMSO-dd 6 ), chemical shifts: 12.45(s, 1H, CONH), 9.03(s, 1H, CSNH), 7.68(s, 2H, NH 2 ), 2.93 (s, 3H, thiadiazolyl-CH 3 ).

Embodiment 2

[0039] Compound WSX-10: Preparation and structure identification of 2-amino-5-(4-methyl-1,2,3-thiadiazol-5-yl)-1,3,4-thiadiazole

[0040] Add 1-(4-methyl-1,2,3-thiadiazole-5-carbonyl)thiosemicarbazide (3.6 g, 16.6 mmol) and concentrated sulfuric acid (10 ml) into a 100 ml round bottom flask, room temperature Stir under low pressure for 6 hours, then pour the reaction solution into 80 ml of ice water, adjust the pH value to 9-10 with 25% ammonia water, a large amount of yellow solids are precipitated, after standing, they are suction filtered, washed with water and ethanol respectively, and dried Obtain pure product, yield 90%; Melting point: 246-248 degree centigrade; Carry out 1 Determination of HNMR, 1HNMR (solvent: DMSO-d 6 ), chemical shift: 7.87(s, 2H, NH 2 ), 2.85(s, 3H, thiadiazolyl-CH 3 ).

Embodiment 3

[0042] Compound WSX-59: N-[5-(4-methyl-1,2,3-thiadiazol-5-yl)-1,3,4-thiadiazol-2-yl]-4methyl- Preparation and Structure Identification of 1,2,3-Thiadiazole Carboxamide

[0043] In a 100 ml round bottom flask was added 2-amino-5-(4-methyl-1,2,3-thiadiazol-5-yl)-1,3,4-thiadiazole (0.21 g, 1.1 mmol ), dichloromethane (15 ml) and triethylamine (0.22 g, 2.2 mmol), 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride (0.27 g, 1.5 mmol) Dissolve in dichloromethane (5 ml), slowly drop into the reaction solution under stirring at room temperature, after dropping, continue to react at room temperature for 5 hours, TLC board monitors that the raw materials have been reacted, and obtain a yellow solid by suction filtration, the mother liquor is concentrated, suction filtration, and combined The solid was washed with dilute hydrochloric acid, water and methanol respectively, and the pure product was obtained after drying, with a yield of 60%; melting point: 240 degrees Celsius (decomposition); ...

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Abstract

The invention provides 1,2,3-thiadiazole-1,3,4-thiadiazole derivatives, and a preparation method and application thereof. The invention relates to 1,2,3-thiadiazole-containing heterocyclic compounds with the chemical structural general formula shown as the specification. The invention discloses the structural general formula of the compounds, a synthesizing method of the compounds, application ofthe compounds serving as pesticides, bactericides, anti-plant-virus agents and plant activating agents, and a process for preparing the pesticides, the bactericides, the anti-plant-virus agents and the plant activating agents by mixing the compounds and agriculturally acceptable adjuvants or synergists. The invention also discloses application of the compounds when the compounds are combined withcommodities of the pesticides, the bactericides, the anti-plant-virus agents and the plant activating agents in prevention and control of agricultural, forestry, horticultural and health diseases, insect pests and virus diseases, and a preparation method of the compounds.

Description

technical field [0001] The technical scheme of the present invention relates to heterocyclic compounds containing 1,2-oxadiazole, in particular to 1,2,3-thiadiazole bi-1,3,4-thiadiazole derivatives. Background technique [0002] Thiadiazoles are an important class of heterocyclic compounds, which occupy an important position in the research and development of pesticides and medicines. Thiadiazoles include 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole and 1,2,5-thiadiazole. Among them, 1,2,3-thiadiazole and 1,3,4-thiadiazole compounds have a wide range of biological activities, such as 1,2,3-thiadiazole compounds have anti-inflammatory, anthelmintic, bactericidal, weeding, Anticancer, regulating plant growth and other biological activities (Boschelli, et al., J.Med.Chem.1993, 36: 1802; Saad H., Indian J.Chem, 1996, 35B: 980; Fan Z.J., et al., J.Agric.Food Chem.2009,57:4279; Bakulev, et al., The Chemistry of 1,2,3-thiadiazole, 2004, John WIley & Sons, Inc.), In add...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/135C07D401/14C07D413/14A01N53/12A01N43/828A01P1/00A01P3/00A01P7/04
Inventor 范志金张聚方王守信黄杰张正财付一峰房震李岳东国丹丹赵晖
Owner NANKAI UNIV
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