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

doi:10.11944/j.issn.1000-0518.2016.06.150322

Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (6): 668-676.DOI: 10.11944/j.issn.1000-0518.2016.06.150322

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

ZHANG Hanyun,LIU Manyun,YAN Gang,SHI Deqing()

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

Received:2015-09-02 Accepted:2015-12-10 Published:2016-06-01 Online:2016-06-01
Contact: SHI Deqing
Supported by:
Supported by the National Natural Science Foundation of China(No.21342004), the Self-Determined Research Funds of CCNU from the Colleges' Basic Research and Operation of MOE(No.CCNU14A02007)

Abstract

Abstract:

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.

Key words: diamide, aryloxy acetic acid, phytoene desaturase inhibitor, Ugi reaction, herbicidal activity

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.

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

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