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Synthesis of N-Cyclohexyl 2-{N-(3-Trifluoromethylphenyl)-[3-(trifluo-romethyl)benzoyl, 2-(substitutedphenoxy)propionyl, 2-(4,6-dime-thoxypyrimidinyl-2-oxy)benzoyl]-amino}-substituted-phenyl-acetamides via Ugi Reaction and Their HerbicidalActivity Evaluation
Received date: 2015-07-03
Revised date: 2015-07-22
Online published: 2015-08-31
Supported by
Project supported by the National Natural Science Foundation of China (No. 21342004) and the Natural Science Foundation of Hubei Province (No. 2015CKB741).
In order to find novel high active herbicidal lead compound, a series of N-cyclohexyl 2-{N-(3-trifluoromethyl-phenyl)-[3-(trifluoromethyl)benzoyl, 2-(substitutedphenoxy)propionyl, 2-(4,6-dimethoxypyrimidinyl-2-oxy)benzoyl]-amino}-substitutedphenylacetamides 3a～3i were designed and synthesized by introducing 3-trifluoromethylbenzoyl, 2-aryloxy-pro-pionyl or 2-(4,6-dimethoxypyrimidin-2-yloxy)benzoyl and 3-trifluoromethyl phenyl moieties into the molecular skeleton via the Ugi reaction. Their structures were characterized by IR, 1H NMR, EI-MS, and elemental analyses. The preliminary bioassay (in vitro) indicated that some of compounds 3 displayed moderate to good herbicidal activity against Brassica campestris L at the concentration of 100 mg/L. The glasshouse bioassay (in vivo) showed that some of compounds 3 exhibited good herbicidal activities against B. campestris, A. retroflexus, E. crusgalli and D. sanguinalis in pre-emergence treatment at a dose of 1500 g/ha.
Hu Hanning , Li Anling , Zhang Hanyun , Shi Deqing . Synthesis of N-Cyclohexyl 2-{N-(3-Trifluoromethylphenyl)-[3-(trifluo-romethyl)benzoyl, 2-(substitutedphenoxy)propionyl, 2-(4,6-dime-thoxypyrimidinyl-2-oxy)benzoyl]-amino}-substituted-phenyl-acetamides via Ugi Reaction and Their HerbicidalActivity Evaluation[J]. Chinese Journal of Organic Chemistry, 2015 , 35(10) : 2162 -2167 . DOI: 10.6023/cjoc201507003
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