Details

Autor(en) / Beteiligte

• Liu, Xing-Hai
• Zhao, Wen
• Shen, Zhong-Hua
• Xing, Jia-Hua
• Xu, Tian-Ming
• Peng, Wei-Li

Titel

Synthesis, nematocidal activity and SAR study of novel difluoromethylpyrazole carboxamide derivatives containing flexible alkyl chain moieties

Ist Teil von

• European journal of medicinal chemistry, 2017-01, Vol.125, p.881-889

Ort / Verlag

France: Elsevier Masson SAS

Erscheinungsjahr

2017

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• A series of novel difluoromethylpyrazole carboxamides derivatives were synthesized by introduction of flexible alkyl chain. Nematicidal bioassay results showed that some of them exhibited good control efficacy against M. incognita, which indicated that these difluoromethylpyrazole carboxamides derivatives might be potential novel lead compounds for discovery new nematicides. The nematicidal activity was affected by the substituted position in the molecule, especially the substitution group on the alkyl chain. It was found that the compound 6-9 and 6-23 possess about 50% inhibition effect against M. incognita even at 5.0 and 1.0 mg L−1. Meanwhile, greenhouse field trial showed the nematicidal activity of compound 6-9 is a litter weaker than that of Abamectin. The mammalian toxicology results indicated that compound 6-9 was a low-toxicity and low-sensitive compound. In conclusion compound 6-9 is a potential candidate for further development. In addition, the molecular docking simulations revealed that compounds 6 with a flexible NHCOO show its binding affinities for the acetylcholine receptor (AChR), which may provide useful information for further design novel nematicides. [Display omitted] •The novel difluoromethylpyrazole derivatives containing flexible alkyl chain moieties were designed and synthesized.•Compound 6-9 and 6-23 possessed most good nematocidal activity against M. incognita with low toxicity.•Compound 6-9 also exhibited low toxicity against rat and no eye or skin sensitization against rabbit.•Molecular docking study suggested that the flexible NHCOO group of compound 6-9 inhibited the acetylcholine receptor (AChR).