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Synthesis and Herbicidal Activity of Acylpyrazole Derivatives Containing 1,2,3‐Thiadiazole Moiety
Author(s) -
Cheng Feng,
Shi DeQing
Publication year - 2012
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.790
Subject(s) - chemistry , moiety , brassica , bioassay , echinochloa , chloride , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , horticulture , botany , weed , biology , genetics
A series of novel acylpyrazole derivatives containing 1,2,3‐thiadiazole ring 3a – 3m were synthesized by the condensations of 1‐phenyl‐3‐methyl‐4‐(substituted benzal or 4‐methyl‐1,2,3‐thiadiazole‐5‐carbonyl)‐5‐hydroxypyrazole 2 with 4‐methyl‐1,2,3‐thiadiazole‐5‐carbonyl chloride or substituted benzoyl chloride. Their structures were confirmed by IR, 1 H‐NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays showed that some of the title compounds 3 exhibited moderate to good herbicidal activities against dicotyledonous plants ( Brassica campestris L.) at the concentration of 100 mg/L. For example, compounds 3e , 3f , 3g , and 3k possessed 74.6%, 72.2%, 70.3%, and 84.5% inhibition against B. campestris L., respectively, whereas commercially available herbicide Sulcotrione showed only 35.0% inhibition at the same concentration. Moreover, these compounds displayed higher herbicidal activity against B. campestris L. than Echinochloa crus‐galli . However, these compounds showed weak activities at the concentration of 10 mg/L.