Synthesis and Fungicidal Activity of 5‐Aryl‐1‐(aryloxyacetyl)‐3‐(tert‐butyl or phenyl)‐4‐(1H‐1, 2, 4‐triazol‐1‐yl)‐4, 5‐dihydropyrazole. (7th March 2013)

• Record Type: Journal Article
• Authors: Mao, Hui‐Yu; Song, Hong; Shi, De‐Qing
• Is Part Of: Journal of heterocyclic chemistry. Volume 50:Number 2(2013:Mar.)
• Page Start: 216
• Page End: 219
• Publication Date: 2013-03-07
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.934
• Languages: English
• ISSNs: 0022-152X

Abstract

<abstract abstract-type="main" xml:lang="en" id="jhet934-abs-0001"> <title> <x xml:space="preserve">Abstract</x> </title> <p id="jhet934-para-0002">A series of novel 5‐aryl‐1‐(aryloxyacetyl)‐3‐(<italic>tert</italic>‐butyl or phenyl)‐4‐(1<italic>H</italic>‐1, 2, 4‐triazol‐1‐yl)‐4, 5‐dihydropyrazole <xref ref-type="link" rid="jhet934-fig-0001">1</xref>–<xref ref-type="link" rid="jhet934-fig-0001">1</xref> were synthesized by the annulation of 2‐aryloxyacetohydrazides with 3‐aryl‐1‐<italic>t</italic>‐butyl (or phenyl)‐2‐(1<italic>H</italic>‐1, 2, 4‐triazol‐1‐yl)prop‐2‐en‐1‐ones (<xref ref-type="link" rid="jhet934-fig-0001">1</xref>) in the presence of a catalytic amount of acetic acid. Compounds <xref ref-type="link" rid="jhet934-fig-0001">1</xref> were obtained by the Knoevenagel reactions of 1‐<italic>t</italic>‐butyl (or phenyl)‐2‐(1<italic>H</italic>‐1, 2, 4‐triazol‐1‐yl)ethanone (<xref ref-type="link" rid="jhet934-fig-0001">1</xref>) with aromatic aldehydes in the presence of piperidine. Their structures were confirmed by IR, <sup>1</sup>H‐NMR, ESI‐MS, and elemental analyses. The preliminary bioassay indicated that some compounds displayed moderate to excellent fungicidal activity. For example, compounds <xref ref-type="link" rid="jhet934-fig-0001">1</xref>, <xref ref-type="link" rid="jhet934-fig-0001">1</xref>, and <xref ref-type="link" rid="jhet934-fig-0001">1</xref> possessed 100% inhibition against <italic>Cercospora arachidicola</italic> Hori at the concentration of 50 mg/L.</p> </abstract>