Journal
CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 43, Issue 7, Pages 2462-2475Publisher
SCIENCE PRESS
DOI: 10.6023/cjoc202301008
Keywords
pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine; synthesis; herbicidal activity
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In this study, 42 N-containing fused heterocyclic compounds were synthesized and their structures were confirmed. These compounds showed remarkable herbicidal activities against monocotyledons and dicotyledons plants.
To discover N-containing fused heterocyclic compounds with novel structure and excellent herbicidal activity, forty-two pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives (I-1 similar to I-42) were synthesied using 2-(alkylthio)-5carbonitrile-6-(methylthio)pyrimidine-4-aminos as starting materials. Their structures were clearly confirmed by melting point, H-1 NMR, C-13 NMR, infrared absorption spectroscopy (IR), and high-resolution mass spectra (HRMS). The preliminary bioassay indicated that many target compounds exhibited remarkable herbicidal activities against the monocotyledons (Triticum aestivum L., Echinochloa crusgalli, and Sorghum bicolor) and dicotyledons (Raphanus sativus, Brassica campestris, and Cucumis sativus) at the concentration of 100 mg/L. Especially, compounds I-13, I-14, I-23, I-25 and I-30 similar to I-42 showed excellent herbicidal activities against the roots and stalks of the six test plant at 100 mg/L with 100% inhibition rates.
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