Synthesis and Herbicidal Activity of 2-Aroxy-propanamides Containing Pyrimidine and 1,3,4-Thiadiazole Rings

被引：5
作者：
Liu, Man-Yun [1 ]
Shi, De-Qing [1 ]
机构：
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2014年 / 51卷 / 02期
关键词：
ANTIINFLAMMATORY ACTIVITIES; DERIVATIVES; KIH-6127;
D O I：
10.1002/jhet.1853
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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, H-1-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 100mg/L. However, these compounds did not possess inhibitory activity against Echinochloa crus-galli at the tested concentrations.
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收藏
页码：432 / 435
页数：4
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