Citation: ZHANG Hanyun, LIU Manyun, YAN Gang, SHI Deqing. Synthesis of Diamides Containing of 2-Aryloxyacetyl and meta-Trifluoromethylphenyl Moieties and Their Herbicidal Activity[J]. Chinese Journal of Applied Chemistry, ;2016, 33(6): 668-676. doi: 10.11944/j.issn.1000-0518.2016.06.150322 shu

Synthesis of Diamides Containing of 2-Aryloxyacetyl and meta-Trifluoromethylphenyl Moieties and Their Herbicidal Activity

1.
Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China

Corresponding author: SHI Deqing,
Received Date: 2 September 2015
Available Online: 2 November 2015
Fund Project:

Based on the combination of different active groups with different herbicidal modes of action, a series of diamide compounds 3a~3v containing of 2-(aryloxy)acetyl and meta-trifluoromethylphenyl moieties were designed and synthesized via the four-component Ugi reaction. Their structures were characterized by IR, ¹H NMR, EI-MS, and elemental analyses. The glass house bioassay(in vivo) shows that some of compounds 3 exhibit moderate to good herbicidal activities against B.campestris, A.retroflexus, E.crusgalli, and D.sanguinalis at a dose of 1.5 kg/ha. For example, compound 3r displays 100% inhibition aganist both of A.retroflexus and D.sanguinalis in the pre-emergence treatment, it also exhibits 100% inhibition aganist D.sanguinalis in the post-emergence treatment. In addition, the preliminary structure-activity relationships are also discussed.
- diamide,
- aryloxy acetic acid,
- phytoene desaturase inhibitor,
- Ugi reaction,
- herbicidal activity
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