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4-methyl-1,2,3-thiadiazole-5-formyl urea compounds and preparation method and application thereof

A kind of technology of thiadiazole and compound, applied in the field of 4-methyl-1

Inactive Publication Date: 2011-02-16
LIER CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Formylurea derivatives containing 1,2,3-thiadiazole and their biological activities have not been reported

Method used

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  • 4-methyl-1,2,3-thiadiazole-5-formyl urea compounds and preparation method and application thereof
  • 4-methyl-1,2,3-thiadiazole-5-formyl urea compounds and preparation method and application thereof
  • 4-methyl-1,2,3-thiadiazole-5-formyl urea compounds and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Preparation of intermediate 4-methyl-1,2,3-thiadiazole-5-carboxamide Ⅱ

[0036] In a 500 ml two-necked flask, add 30 ml of 25% ammonia water, 5 ml of triethylamine, and 50 ml of tetrahydrofuran, and drop 5 grams of 4- Methyl-1,2,3-thiadiazole-5-carbonyl chloride I was added dropwise in 15 minutes. Stirring was continued for 2 hours under ice-cooling and then at room temperature for 7 hours. After the reaction was completed, separate the liquid with a separatory funnel, extract the aqueous layer 3 times with 15 ml of tetrahydrofuran, combine the organic layers, dry with anhydrous sodium sulfate overnight, remove the anhydrous sodium sulfate by suction filtration, remove the solvent by rotary evaporation, and there is a white flaky solid Generated as 4-methyl-1,2,3-thiadiazole-5-carboxamide II.

Embodiment 2

[0038] Preparation of intermediate 4-methyl-1,2,3-thiadiazole-5-formyl isocyanate Ⅲ

[0039] Take a 100 ml three-necked flask, add 2 grams of 4-methyl-1,2,3-thiadiazole-5-carboxamide II and 15 ml of 1,2-dichloroethane, stir to make the amide in the solvent Disperse evenly, add 4.3 g of oxalyl chloride diluted with 5 ml of 1,2-dichloroethane dropwise with a dropping funnel under ice bath, dropwise in 30 minutes, then stir at room temperature for 1 hour, and then heat to 80 degrees Celsius After reflux for 7 hours, the reaction solution changed from white to turbid to a light yellow transparent solution, and the color gradually became darker after heating. After the reaction was completed, the solvent was removed by rotary evaporation to obtain the product 4-methyl-1,2,3-thiadiazole-5-formylisocyanate III, which was directly used in subsequent reactions without further purification.

Embodiment 3

[0041] Compound GDD-1: Synthesis and structure identification of N-(4-nitrophenyl)-N’-(4-methyl-1,2,3-thiadiazole-5-formyl)urea

[0042] Add 2.7 millimoles of p-nitroaniline and 20 milliliters of 1,2-dichloroethane into a 100-ml round-bottomed flask, stir until the p-nitroaniline is completely dissolved, then add 3 mmoles of 4-methyl-1 dropwise under stirring, 2,3-Thiadiazole-5-formyl isocyanate, after 15 minutes of dropwise addition, a precipitate was formed immediately, stirred at room temperature for 8 hours, after the reaction was completed, stood still, separated by suction filtration to obtain a solid product, and the filtrate was rotatably evaporated to remove the solvent , with volume ratio of 1:3 ethyl acetate: sherwood oil recrystallization and put it in the refrigerator, precipitated solid, combined solid product, with volume ratio of 1:3 ethyl acetate: sherwood oil washed and dried to obtain the product; Melting point: 178-180 degrees Celsius, yield 58%. NMR data ...

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Abstract

The invention provides formyl urea derivatives containing 1,2,3-thiadiazole perssad and a preparation method and application thereof, and relates to heterocyclic compounds containing 1,2,3-thiadiazole, which have the chemical construction general formula shown in the specification of the invention. The invention discloses the construction general formula, a synthesis method, application of the compounds used as insecticides, fungicides, anti-plant virus agents and plant activating agents, and the process for preparing insecticides, fungicides, anti-plant virus agents and plant activating agents by mixing the compounds with acceptable auxiliaries or synergists in agriculture, the invention also discloses a preparation method and application of a combination of the compounds and commodity insecticides, fungicides, anti-plant virus agents and plant activating agents in disease and insect prevention and control in agriculture, forestry and gardening.

Description

technical field [0001] The technical solution of the present invention relates to 1,2-oxadiazole-containing compounds, in particular to 4-methyl-1,2,3-thiadiazole-5-formylurea compounds. Background technique [0002] Benzoyl urea compounds have a wide range of biological activities, and 3-bromopropionamide benzoyl urea has medicinal biological activity (Li Jiannong, etc. Acta Pharmaceutica Sinica. 2004, 39 (7): 491-495; Song Dan-Qing , et al.Bioorg.Med.Chem.Let., 2009,19: 755-758); In terms of pesticides, since 1972, it was found that benzoylureas (BPUs) compounds have an inhibitory effect on insect moulting, there have been More than 10 commercial varieties have been released, and the research on BPUs insecticides has won the 2000 "Presidential Green Chemistry Challenge Award" in the United States (Yan Menggang, et al. Chemical Education, 2009, 5: 75-77); BPUs insect growth regulators It is a chitin synthesis inhibitor, which interferes with the chitin synthesis of target ...

Claims

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Application Information

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IPC IPC(8): C07D285/06C07D473/00C07D417/12A01P3/00C07D417/14A01P7/04A01P7/02A01N47/34A01N47/36A01P1/00
Inventor 范志金国丹丹范谦杨维清付一峰赵晖王守信王唤米娜
Owner LIER CHEM CO LTD
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