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5-halogenated methyl-1,2,3-thiadiazole compound and preparation method and use thereof

A technology of thiadiazoles and halomethyl, which is applied in the field of 5-halomethyl-1, can solve the problem of rare pesticide varieties

Inactive Publication Date: 2012-11-21
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Heterocyclic compounds have a wide range of biological activities, and many patents with biological activities contain heterocyclic compounds. The biological activity of 1,2,3-thiadiazole derivatives is attracting widespread attention. The inventor's previous research found that 1, 2,3-thiadiazole derivatives have very good activity of inducing plant resistance to viral diseases and fungal diseases, and methiamide is in the process of industrialization; the most successful plant activator in commercial development, benzothiadiazole (BTH ) and TDL (TDL) are also derivatives of 1,2,3-thiadiazole; however, commercialized 1,2,3-thiadiazole pesticide varieties are rare

Method used

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  • 5-halogenated methyl-1,2,3-thiadiazole compound and preparation method and use thereof
  • 5-halogenated methyl-1,2,3-thiadiazole compound and preparation method and use thereof
  • 5-halogenated methyl-1,2,3-thiadiazole compound and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Preparation and structure identification of compound 5-chloromethyl-1,2,3-thiadiazole-4-carboxylic acid ethyl ester (ZHH-FC)

[0048] 10 ml of carbon tetrachloride was added to a 50 ml round bottom flask, followed by ethyl 5-methyl-1,2,3-thiadiazole-4-carboxylate (1.04 g, 6.05 mmol), N-chloro Succinimide (NCS) (1.27 grams, 7.13 mmol), azobisisobutyronitrile (AIBN) (0.10 grams, 0.61 mmol), the reaction system was refluxed for 6 hours under stirring, after the reaction was completed, filter The product, the solid was washed with 10 ml of carbon tetrachloride × 3, the organic phases were combined, the solvent was evaporated under reduced pressure, and the 200-300 mesh silica gel column chromatography was used to obtain 5-chloromethyl-1,2,3-thiadiazole- 4-Ethyl formate, the eluent is petroleum ether at 60-90 degrees Celsius: ethyl acetate, the volume ratio is 10:1, the yield is calculated with the pure product obtained, and the yield is 13%; carry out 1 Determination of HN...

Embodiment 2

[0050] Preparation and structure identification of the compound 5-bromomethyl-1,2,3-thiadiazole-4-carboxylic acid ethyl ester (ZHH-4)

[0051] Add 10 ml of carbon tetrachloride to a 50 ml round bottom flask, then add 5-methyl-1,2,3-thiadiazole-4-carboxylic acid ethyl ester (1.04 g, 6.05 mmol), N-bromo Succinimide (NBS) (1.27 grams, 7.13 mmol), azobisisobutyronitrile (AIBN) (0.10 grams, 0.61 mmol), the reaction system was refluxed for 6 hours under stirring, after the reaction was completed, filter The product, the solid was washed with 10 ml of carbon tetrachloride × 3, the organic phases were combined, and the solvent was distilled off under reduced pressure to obtain 5-bromomethyl-1,2,3-thiadiazole- 4-Ethyl formate, the eluent is petroleum ether at 60-90 degrees Celsius: ethyl acetate, the volume ratio is 10:1, the yield is calculated with the pure product obtained, and the yield is 24%; carry out 1 Determination of HNMR, 1 HNMR (solvent: CDCl 3 , chemical shift): 5.095 (...

Embodiment 3

[0053] Preparation and structure identification of compound 5-iodomethyl-1,2,3-thiadiazole-4-carboxylic acid ethyl ester (ZHH-14)

[0054] Add 5-bromomethyl-1,2,3-thiadiazole-4-carboxylic acid ethyl ester (0.20 g, 0.8 mmol) in a 50 ml round bottom flask, add 15 ml solvent acetone, then add potassium iodide (0.20 g , 1.2 mmol), stirred at room temperature for 20 hours, filtered out the solid in the solution, evaporated the solvent under reduced pressure and obtained 5-iodomethyl-1,2,3-thiadiazole- with 200-300 mesh silica gel column chromatography 4-Ethyl formate, the eluent is petroleum ether at 60-90 degrees Celsius: ethyl acetate, the volume ratio is 5: 1, the yield is calculated with the pure product obtained, the yield is 59%, and the 1 Determination of HNMR, 1 HNMR (solvent: CDCl 3 ), chemical shift: 5.089 (s, 2H, CH 2 ), 4.578-4.525 (q, 2H, J=7.2Hz, J=14.4Hz, CH 2 ), 1.515-1.479 (t, 3H, J=7.2Hz, CH 3 ), the compound's 1 The H NMR data show that its chemical structu...

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Abstract

The invention provides a 5-halogenated methyl-1,2,3-thiadiazole derivative and a preparation method and use thereof. The invention relates to heterocyclic compounds containing the 1,2,3-thiadiazole which have a chemical structure general formula shown in the specifications. The invention discloses the general formula and a synthesis method of the compounds, the use of the compounds as pesticide, bactericide, plant virus resisting agent and plant activator, and the process for preparing the pesticide, the bactericide, the plant virus resisting agent and the plant activator by mixing the compounds and an agriculturally acceptable assistant or synergist. The invention further discloses the use of the compounds in preventing and controlling the agricultural, forest and garden diseases, insectdamages and virus diseases by combining the compounds with the commodity pesticide, the bactericide, the plant virus resisting agent and the plant activator, and the preparation method.

Description

technical field [0001] The technical scheme of the present invention relates to heterocyclic compounds containing 1,2-oxadiazole, in particular to 5-halogenated methyl-1,2,3-thiadiazole derivatives. Background technique [0002] Heterocyclic compounds have a wide range of biological activities, and many patents with biological activities contain heterocyclic compounds. The biological activity of 1,2,3-thiadiazole derivatives is attracting widespread attention. The inventor's previous research found that 1, 2,3-thiadiazole derivatives have very good activity of inducing plant resistance to viral diseases and fungal diseases, and methiamide is in the process of industrialization; the most successful plant activator in commercial development, benzothiadiazole (BTH ) and TDL (TDL) are also derivatives of 1,2,3-thiadiazole; however, commercialized 1,2,3-thiadiazole pesticide varieties are rare. Halogen is an important active group for biological activity. The introduction of hal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/06A01N43/828A01P3/00A01P1/00A01P7/04A01P21/00
Inventor 范志金王守信付一峰赵晖国丹丹王唤米娜黄杰
Owner NANKAI UNIV
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