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3-(1,3,4- thiadiazole)-1,3-benzooxazine-2-acetone compounds and application thereof

A ketone compound and thiadiazolyl-based technology, which is applied in the field of pesticides, can solve problems that have not been reported, and achieve good bactericidal activity, easy-to-obtain materials, and simple synthesis methods

Inactive Publication Date: 2013-12-25
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the research on 1,3-benzoxazin-2-ones containing 1,3,4-thiadiazolyl substitution has not been reported yet.

Method used

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  • 3-(1,3,4- thiadiazole)-1,3-benzooxazine-2-acetone compounds and application thereof
  • 3-(1,3,4- thiadiazole)-1,3-benzooxazine-2-acetone compounds and application thereof
  • 3-(1,3,4- thiadiazole)-1,3-benzooxazine-2-acetone compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: 3-(5-Methyl-1,3,4-thiadiazol-2-yl)-3,4-dihydro -2H- Synthesis of 1,3-Benzoxazin-2-ones.

[0023] Add 2.26 mmol 2-((5-methyl-1,3,4-thiadiazol-2-yl)aminomethyl)phenol into a 100 mL round bottom flask, heat to dissolve with 35 mL toluene, pour into the flask Add 6.78 mmol of triethylamine, weigh 1.13 mmol of triphosgene and dissolve it in toluene, add the toluene solution of triphosgene dropwise in an ice bath, after the dropwise addition, heat and reflux at 95°C for 2 h (TLC tracking detection), after cooling, Add an appropriate amount of ethyl acetate to the reaction system, filter with suction, wash the filter cake with ethyl acetate, and purify by column chromatography to obtain a white solid with a yield of 56.5% and a melting point (mp): 212.1-212.4 °C.

[0024] 1 H NMR (CDCl 3 , 500 MHz) δ: 7.35(t, J=7.5, 1H), 7.29(t, J=7.5, 1H), 7.23(t, J=7.5, 1H), 7.14(d, J=8.5, 1H), 5.354(s, 2H), 2.717(s, 3H).

[0025] 13 C NMR ( CDCl 3 , 125 MHz), δ: 163.23, 1...

Embodiment 2

[0027] Example 2: 3-(5-Propyl-1,3,4-thiadiazol-2-yl)-3,4-dihydro -2H- Synthesis of 1,3-benzoxazin-2-one.

[0028] Add 3 mmol of 2-((5-propyl-1,3,4-thiadiazol-2-yl)aminomethyl)phenol into a 100 mL round bottom flask, heat to dissolve with 35 mL of toluene, pour into the flask Add 9 mmol of triethylamine, weigh 1.5 mmol of triphosgene and dissolve it in toluene, add the toluene solution of triphosgene dropwise in an ice bath, after the dropwise addition, heat and reflux at 95°C for 2 h (TLC tracking detection), after cooling, Add an appropriate amount of ethyl acetate to the reaction system, filter with suction, wash the filter cake with ethyl acetate, and purify it by column chromatography to obtain a white solid with a yield of 20.8% and a melting point (mp): 178.2-178.4 °C.

[0029] 1 H NMR (CDCl 3 , 500 MHz) δ: 735(t, 1H), 7.3(d, J=7.0, 1H), 7.21~7.24(m, 1H), 7.13(d, J=8.0, 1H), 5.35(s, 2H ), 3.01(t, J=7.5, 2H ), 1.80~1.88(m, 2H ), 1.04(t, 3H).

[0030] 13 C NMR (C...

Embodiment 3

[0032] Example 3: 3-(5-isopropyl-1,3,4-thiadiazol-2-yl)-3,4-dihydro -2H- Synthesis of 1,3-Benzoxazin-2-ones.

[0033] Add 2 mmol of 2-((5-propyl-1,3,4-thiadiazol-2-yl)aminomethyl)phenol into a 100 mL round bottom flask, heat to dissolve with 35 mL of toluene, pour into the flask Add 6 mmol of triethylamine, weigh 1 mmol of triphosgene and dissolve it in toluene, add the toluene solution of triphosgene dropwise in an ice bath, after the dropwise addition, heat and reflux at 95 °C for 2 h (TLC tracking detection), after cooling, Add an appropriate amount of ethyl acetate to the reaction system, filter with suction, wash the filter cake with ethyl acetate, and purify it by column chromatography to obtain a white solid with a yield of 71.70% and a melting point (mp): 159.8-161.0 °C.

[0034] 1 H NMR (CDCl 3 , 500 MHz) δ: 7.34(s, 1H), 7.30(t, 1H), 7.21~7.25(m, 1H), 7.12(t, 1H), 5.34(s, 2H), 3.38~3.41(m, 1H ), 1.44~1.46(m, 6H).

[0035] 13 C NMR (CDCl 3 , 125 MHz) δ: 174.22...

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Abstract

The invention discloses novel 3-(1,3,4- thiadiazole)-1,3-benzooxazine-2-acetone compounds with structural formulas shown in a formula (I); in the formula (I), a substituent group R<1> is H, R<2> is H, R<3> is H and R<4> is 5-methyl-1,3,4- thiadiazole or 5-propyl-1,3,4- thiadiazole or 5-isoproyl-1,3,4- thiadiazole; and the substituent group R<2> is (-)Br, the R<1> is H, the R<3> is H and the R<4> is 5-methyl-1,3,4- thiadiazole or 5-ethyl-1,3,4- thiadiazole. The compounds have stronger sterilization activity, and can be used for preparing agricultural fungicides.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a class of novel 3-(1,3,4-thiadiazolyl)-1,3-benzoxazin-2-one compounds. Background technique [0002] 1,3-Benzoxazin-2-one compounds usually have a wide range of biological activities, such as some are active against leukemia L1210 cells and human tumor MAD-MB231 cells; some have good bactericidal activity; Ulcer and anti-inflammatory activity; some have herbicidal activity. Therefore, 1,3-benzoxazin-2-one compounds occupy a very important position in the field of medicine. In addition, 1,3,4-thiadiazole compounds are a kind of five-membered heterocyclic compounds containing nitrogen and sulfur elements, which have good biological activities such as herbicide, insecticide, fungicide, plant growth regulation, anti-cancer, anti-inflammation, etc. , where 1,3,4-thiadiazolyl is an important pharmacophore. However, the research on 1,3-benzoxazin-2-ones containing 1,3,4-thiadiazo...

Claims

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Application Information

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IPC IPC(8): C07D417/04A01N43/86A01P3/00
Inventor 唐子龙焦文杰
Owner HUNAN UNIV OF SCI & TECH
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