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Syntehsis and activity of triazolo-pyrimido-thioacetyl hydrazone compounds

A technology of azolopyrimidine thioacetyl and azolopyrimidine, which is applied in the synthesis and application field of triazolopyrimidine thioacetylhydrazone compounds, can solve rare problems and achieve the effect of significant specific killing activity

Inactive Publication Date: 2004-02-11
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, this type of compound is mainly used as herbicides, such as DE498 (Broadgrass Clear), DE511, TP4189, etc., but the reports of compounds containing triazolopyrimidine structural units as fungicides are rare (EP550113, 1993)

Method used

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  • Syntehsis and activity of triazolo-pyrimido-thioacetyl hydrazone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0021] Example 2 preparation of

[0022] Dissolve 0.5 mol of ethyl 5-amino-1,2,4-triazole-3-thioacetate and 0.5 mol of dimethyl malonate in 200 ml of absolute ethanol, then add 215 g of 25% sodium methoxide methanol solution, reflux reaction for 60 hours, cooling, suction filtration, washing with absolute ethanol twice, the solid was first dissolved in 1000ml of water, then acidified with concentrated hydrochloric acid, and a white solid was obtained by suction filtration with a yield of 82%, m.p.99~100°C .

[0023] Elemental Analysis: Calculated C% 40.03 H% 3.70 N% 20.74

[0024] Measured value C% 40.35 H% 3.23 N% 21.05

Embodiment 3

[0025] Example 3 preparation of

[0026] Add 0.5mol of 5,7-dihydroxy-1,2,4-triazolo[1,5-a]pyrimidine-2-thioacetic acid ethyl ester and 1.5mol of phosphorus oxychloride into 1200ml of acetonitrile, Reflux for 3 hours, stand overnight, filter, remove the solvent from the filtrate, then add an equal amount of ice water and dichloromethane, separate the organic phase, dry with anhydrous magnesium sulfate, concentrate until crystals are precipitated, the yield is 81%, m.p.79 ~80°C.

[0027] Elemental Analysis: Calculated C% 35.19 H% 2.61 N% 18.20

[0028] Measured value C% 35.02 H% 2.32 N% 18.55

Embodiment 4

[0029] Example 4 preparation of

[0030] Add 0.05mol of 5,7-dichloro-1,2,4-triazolo[1,5-a]pyrimidine-2-thioacetic acid ethyl ester and 60ml of methanol into the reaction flask, and add 23.5g ( 0.11mol) methanol solution containing 25% sodium methoxide, react at room temperature for 2 hours, add 100ml of water, then neutralize with 3N hydrochloric acid, and filter with suction to obtain a white solid with a yield of 84%, m.p.168-169°C.

[0031] Elemental Analysis: Calculated C% 44.30 H% 4.70 N% 18.79

[0032] Measured value C% 44.02 H% 4.33 N% 18.35

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Abstract

A process for synthesizing a triazolo-pyrimido-thioacytyl hydrozone compound with antibacterial activity is disclosed. The said compound has obvious unique activity to kill the rice Hypochnus when its concentration is 50-200 ppm, so it can be used as disinfectant.

Description

technical field [0001] The invention relates to the synthesis and application technology of a class of triazolopyrimidine thioacetylhydrazone compounds with bactericidal activity. Background technique [0002] In 1985, DOW Corporation of the United States applied for a patent (EP142152) on the synthesis and herbicidal activity of 1,2,4-oxazolo[1,5-a]pyrimidinesulfonamide compounds, thus making triazolopyrimidine derivatives an important topic in the field of pesticides. Another research hotspot. At present, such compounds are mainly used as herbicides, such as DE498 (Bacacyl), DE511, TP4189, etc., but reports of compounds containing triazolopyrimidine structural units as fungicides are rare (EP550113, 1993). Contents of the invention [0003] The purpose of the present invention is to explore compounds with better bactericidal activity, and provide a class of novel triazolopyrimidine acylhydrazone derivatives with bactericidal activity and a preparation method thereof. ...

Claims

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Application Information

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IPC IPC(8): A01N43/90C07D487/04C07D487/06
Inventor 杨光富刘祖明卿湘华陆爱红庄农波
Owner HUAZHONG NORMAL UNIV
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