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

A technology of thiadiazoles and halomethyl, which is applied in the field of 4-halomethyl-1, can solve the problems of rare pesticide varieties and the like

Inactive Publication Date: 2012-07-04
NANKAI UNIV
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  • 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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  • 4-halogenated methyl-1,2,3-thiadiazole compounds and preparation method and application thereof
  • 4-halogenated methyl-1,2,3-thiadiazole compounds and preparation method and application thereof
  • 4-halogenated methyl-1,2,3-thiadiazole compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Preparation and structure identification of compound 4-chloromethyl-1,2,3-thiadiazole-5-carboxylic acid ethyl ester (ZHH-15)

[0046] Add 10 ml of carbon tetrachloride to a 50 ml round bottom flask, then add ethyl 4-methyl-1,2,3-thiadiazole-5-carboxylate (0.67 g, 3.90 mmol), N-chloro Succinimide (NCS) (0.80 g, 5.99 mmol), azobisisobutyronitrile (AIBN) (0.04 g, 0.24 mmol), the reaction system was refluxed for 48 hours under stirring, and after the reaction was finished, filter Product, the solid is washed with 10 ml of carbon tetrachloride × 3, the organic phases are combined, and the solvent is removed under reduced pressure with 200-300 mesh silica gel column chromatography, the eluent is petroleum ether at 60-90 degrees Celsius: ethyl acetate, volume Ratio is 40: 1, calculates yield with gained pure product, yield 26%, carry out 1 Determination of HNMR, 1 HNMR (solvent: CDCl 3 ), chemical shift: 5.282 (s, 2H, CH 2 ), 4.493-4.439 (q, 2H, J=7.2Hz, J=14.4Hz, CH 2 ),...

Embodiment 2

[0049] Preparation and structure identification of the compound 4-bromomethyl-1,2,3-thiadiazole-5-carboxylic acid ethyl ester (ZHH-1)

[0050] Add 10 ml of carbon tetrachloride to a 50 ml round bottom flask, then add 4-methyl-1,2,3-thiadiazole-5-carboxylic acid ethyl ester (0.61 g, 3.55 mmol), N-bromo Succinimide (NBS) (0.72 grams, 4.04 millimoles), azobisisobutyronitrile (AIBN) (0.05 grams, 0.30 millimoles), the reaction system was refluxed for 8 hours under stirring, and after the reaction was finished, filter Product, the solid is washed with 10 ml of carbon tetrachloride × 3, the organic phases are combined, the organic phase is washed 3 times with sodium thiosulfate solution, dried with anhydrous sodium sulfate after washed 3 times with distilled water, and then evaporated under reduced pressure to remove the solvent with 200 -300 mesh silica gel column chromatography, the eluent is sherwood oil of 60-90 degrees centigrade: ethyl acetate, the volume ratio is 40: 1, calcul...

Embodiment 3

[0053] Preparation and structure identification of compound 4-iodomethyl-1,2,3-thiadiazole-5-carboxylic acid ethyl ester (ZHH-13)

[0054] Add 4-bromomethyl-1,2,3-thiadiazole-5-ethyl carboxylate (0.30 g, 1.2 mmol) in a 50 ml round bottom flask, add 15 ml of solvent acetone, then add potassium iodide (0.30 g, 1.8 mmol), stirred at room temperature for 22 hours, filtered out the solid in the solution, and the filtrate decompressed to evaporate the solvent to obtain 4-iodomethyl-1,2,3-thiadiazole- 5-Ethyl formate, the eluent is petroleum ether at 60-90 degrees centigrade: ethyl acetate, the volume ratio is 10: 1, and the yield is calculated with the pure product obtained; the yield is 64%, carried out 1 Determination of HNMR, 1 HNMR (solvent: CDCl 3 ), chemical shift: 5.119 (s, 2H, CH 2 ), 4.488-4.435 (q, 2H, J=7.2Hz, J=14.4Hz, CH 2 ), 1.454-1.419 (t, 3H, J=7.2Hz, CH 3 ), the compound's 1 H NMR data show that its chemical structure is consistent; its physical and chemical p...

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Abstract

The invention provides a class of 4-halogenated methyl-1,2,3-thiadiazole compounds and a preparation method and application thereof, relating to heterocyclic compounds containing 1,2,3-thiadiazole, which have the following chemical general formula as shown in the specification of the invention. The invention discloses the general formula, the synthesis method of the compounds, application of the compounds used as insecticides, disinfectants, antiphytoviral agents and plant activators and the process for preparing insecticides, disinfectants, antiphytoviral agents and plant activators by mixing the compounds with agriculturally acceptable additives or synergists; the invention also discloses the application of combining the compounds with commercial insecticides, disinfectants, antiphytoviral agents and plant activators to prevent and treat diseases, pests, virus diseases in agriculture, forestry and horticulture, and the preparation method of the compounds.

Description

technical field [0001] The technical solution of the present invention relates to heterocyclic compounds containing 1,2-oxadiazole, in particular to 4-halomethyl-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 halogen a...

Claims

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Application Information

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