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Synthesis and Herbicidal Activity of 2‐Aroxy‐propanamides Containing Pyrimidine and 1,3,4‐Thiadiazole Rings
Author(s) -
Liu ManYun,
Shi DeQing
Publication year - 2014
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1853
Subject(s) - chemistry , yield (engineering) , benzaldehyde , bioassay , pyrimidine , proton nmr , ethanol , chloride , amine gas treating , ring (chemistry) , medicinal chemistry , echinochloa , elemental analysis , stereochemistry , nuclear chemistry , organic chemistry , weed , catalysis , materials science , biology , agronomy , metallurgy , genetics
A series of novel N ‐{5‐[2‐(4,6‐dimethoxy‐pyrimidin‐2‐yloxy)‐phenyl]‐[1,3,4]thiadiazol‐2‐yl}2‐aroxy‐propanamides were designed and synthesized by the multistep reactions. 2‐(4,6‐Dimethoxy‐pyrimidin‐2‐yloxy)‐benzaldehyde ( 1 ) reacted with aminothiourea to yield 2 , which undergoes ring closure to give 5‐[2‐(4,6‐dimethoxy‐pyrimidin‐2‐yloxy)‐phenyl]‐[1,3,4]thiadiazol‐2‐amine ( 3 ) in the presence of ferric chloride in refluxing ethanol. 3 reacted with 2‐aroxy‐propionyl chlorides to give the target compounds 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4h , 4i in moderate to good yields. Their structures were confirmed by IR, 1 H‐NMR, EIMS, and elemental analyses. The preliminary bioassay indicated that some of them displayed moderate to good selective herbicidal activity against Brassica campestris L . at the concentration of 100 mg/L. However, these compounds did not possess inhibitory activity against Echinochloa crus‐galli at the tested concentrations.