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Cesium triazoleamide compounds and their preparation and use

A technology of selenium triazole amide and compound, which is applied in the field of selenium triazole amide compound and its preparation and application, can solve the problems of crop phytotoxicity, and achieve the effect of improving safety and selectivity

Inactive Publication Date: 2005-05-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The inventors discovered that adding certain chemicals called sulfone to an active ingredient made from this new substance could improve its effectiveness against unwanted plants while maintaining it's safe during use on our crop plantings. This makes them safer than previous ones but still effective at killing these harmful organisms effectively.

Problems solved by technology

The technical problem addressed in this patented text relates to finding new chemical structures that can effectively kill or control harmful plants without causing damage on their owners while being safe enough against other vegetation.

Method used

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  • Cesium triazoleamide compounds and their preparation and use
  • Cesium triazoleamide compounds and their preparation and use
  • Cesium triazoleamide compounds and their preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of 1-(N,N'-diethylamino)formyl-3-(1H-1,2,4-triazole)selenoyl-2,4,6-trimethylbenzene.

[0031] (1) Synthesis of seleno-semicarbazide:

[0032] Add 24.5g (0.27mol) of crushed thiosemicarbazide, 150ml of absolute ethanol and 16.8ml (0.27mol) of methyl iodide into a 250ml single-necked flask, and react under reflux for one hour. A transparent colorless ethanol solution of S-methylthiosemicarbazide was obtained. Under an ice bath, 15 g (0.405 mol) of sodium borohydride and 21.32 g (0.27 mol) of selenium powder were added to a 500 ml three-necked flask and mixed uniformly. After vacuumizing the system and argon, inject 150ml of absolute ethanol to react violently. After the reaction is over, go to the ice bath. Inject the prepared ethanol solution of S-methylthiosemicarbazide into the system, and react overnight at room temperature. Filter, wash with absolute ethanol, and dry to obtain off-white selenosesemicarbazide with a yield of 90%. Recrystallize from abso...

Embodiment 2

[0044] Synthesis of 1-(N,N'-diethylamino)formyl-3-(1H-1,2,4-triazole)selenoyl-(2,4,6-trimethylbenzene)

[0045] (1) Synthesis of triazolyl selenic acid:

[0046] In a 100ml one-necked flask, add 2.96g (0.02mol) of triazolylselenophene and 25ml of glacial acetic acid to dissolve. Slowly add 20ml of 30% hydrogen peroxide dropwise, and react overnight at room temperature. Filter, wash with cold water and dry to give a white solid. Yield 61%, M.p. 52°C.

[0047] (2) Synthesis of triazolyl selenoyl chloride:

[0048] In a 50ml one-necked flask, add 1.96g (0.01mol) of triazolyl selenic acid and 25ml of thionyl chloride, and react overnight at 40-45°C. Colorless liquid distilled under reduced pressure. Yield 85%.

[0049] (3) Synthesis of triazole selenoyl ester group-(2,4,6-trimethylbenzene):

[0050] 0.68 g (0.005 mol) of 2,4,6-trimethylphenylphenol and 25 ml of chloroform were added to a 50 ml one-necked flask to dissolve, and 0.98 g (0.005 mol) of triazolyl selenoyl chloride...

Embodiment 3

[0054] Synthesis of 1-(N,N'-diethylamino)formyl-3-(1H-1,2,4-triazole)selenoyl-(2,4,6-trimethylbenzene)

[0055] (1) Synthesis of 1H-1,2,4-triazoleselenoyl-(2,4,6-trimethylbenzene):

[0056] Add (2,4,6-trimethylphenyl)selenoether-1H-1,2,4-triazole (refer to example 1) 1.34g (0.005mol) and 30ml of glacial acetic acid in a 100ml single-necked flask, drop slowly Add 10ml of 30% hydrogen peroxide. React at room temperature for 10 hr, extract with dichloromethane, concentrate the extract and separate on a silica gel column (methanol:ethyl acetate=1:8) to obtain a white solid. Yield 78%, M.p. 202-204°C.

[0057] (2) 1-(N,N'-diethylamino)formyl-3-(1H-1,2,4-triazole)selenoyl-(2,4,6-trimethylbenzene) synthesis:

[0058] Using the (2,4,6-trimethylphenyl)selenoyl-1H-1,2,4-triazole synthesized above as a raw material, a white solid was obtained according to the method (4) in Example 2. Yield 87%, M.p. 95-96°C. MS (ESI) m / z: 405 (M+Na + ), element analysis: theoretical value C 50.40%...

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Abstract

This invention relates to triazolacylamine compound containing selenium and its preparation and use. It is prepared by: using substituted amine as start material, preparing its diazo salt, making the said salt condensed with triazoselenophen to obtain aromatic triazoselenide, oxidizing it to obtain triazoselesulfoxide (triazosulfone), condensing triazo sulfone and sulfoxide and aromatic triazoselenide with N,N dialkyl formyl chloride selectively to obtain target products; or oxidizing triazoselenide with dioxide to obtain triazo selenic acid, then preparing Cl selenide, condensing it with substituted phenol to obtain selenonyl triazophenate, condensing it with N,N dialkyl formyl chloride to obtain target product. It can be used as herbicide for crop with good selective ability and safety.

Description

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Claims

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Application Information

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Owner EAST CHINA UNIV OF SCI & TECH
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