Synthesis and herbicidal activity of novel pyrazolo[3,4-d]pyrimidin-4-one derivatives containing aryloxyphenoxypropionate moieties.
The 6-(4-alkoxycarbonylalkoxy)phenoxy-3-alkylthio(alkylsulfonyl)-1-phenyl-5-(substituted phenyl)pyrazolo[3,4-d]pyrimidin-4-ones 6 and 7 have been synthesized via the tandem aza-Wittig and annulation reactions of the corresponding iminophosphoranes 4, aromatic isocyanates, and substituted phenols 2 in 52-98% yields. Their structures were clearly verified by spectroscopic data (IR, (1)H NMR, (13)C NMR, MS, and elemental analysis or X-ray diffraction crystallography). And the results of preliminary bioassay indicated that these title compounds possess potential herbicidal activity against the root of rape and barnyard grass.
Liu
Hui
H
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.
Wang
Hong-Qing
HQ
Liu
Zhao-Jie
ZJ
D018360:Crystallography, X-Ray; D031747:Echinochloa / Q000187:drug effects; D006540:Herbicides / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D018514:Plant Structures / Q000187:drug effects; D011422:Propionates / Q000737:chemistry; D011720:Pyrazoles / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology
D006540:Herbicides; D011422:Propionates; D011720:Pyrazoles; D011743:Pyrimidines