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Chemistry and Industry of Forest Products ›› 2019, Vol. 39 ›› Issue (5): 41-49.doi: 10.3969/j.issn.0253-2417.2019.05.006

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Synthesis, Antibacterial and Herbicidal Evaluation of Camphoric Acid-based Acylhydrazone Compounds

ZHENG Wanli, MA Xianli, ZHOU Xiaoqun, LI Fangyao, XIN Mao, JIANG Caina   

  1. Pharmacy School, Guilin Medical University, Guilin 541004, China
  • Received:2019-03-26 Online:2019-10-25 Published:2019-11-01

Abstract: Camphoric anhydride (2) was prepared via dehydration reaction using camphoric acid (1) as starting material. N-aminocamphorimide (3) was prepared by the acylation of compound2 with hydrazine hydrate. And then, 12 novel camphoric acid-based acylhydrazone compounds4a-4l were synthesized by the condensation reaction between N-aminocamphorimide and polyfluoro-substituted benzaldehyde, thiophene-carbaldehyde or furaldehyde. The target compounds were characterized by means of Fourier transform infrared spectroscopy(FT-IR), nuclear magnetic resonance(1H NMR and 13C NMR) and electrospray ionization-mass spectrometry(ESI-MS). The preliminary bioassay showed that 3, 5-difluorophenyl camphoric acid-based acylhydrazone (4i), 2-trifluoromethylphenyl camphoric acid-based acylhydrazone (4a) and 2, 3-difluorophenyl camphoric acid-based acylhydrazone (4d) exhibited excellent antifungal activities with the inhibition ratios of 90.6%, 85.4% and 82.2% against Botryosphaeria berengeriana at the mass concentration of 50 mg/L. Herbicidal evaluation results showed that most of the compounds had certain inhibitory effects on the growth of rape radicle at 100 mg/L. Among them, the growth inhibition rates of compounds 3-trifluoromethylphenyl camphoric acid-based acylhydrazone (4b), 3, 4-difluorophenyl camphoric acid-based acylhydrazone (4h) and 3-thienyl camphoric acid-based acylhydrazone (4k) on the radicle of rape(Brassica campestris) were 94.7%, 95.6% and 80.6%, respectively. Compound4i has the best overall effect, the inhibition ratio of 90.6% against B.dothidea at 50 mg/L (the activity level was A grade); the root growth inhibition rate of on root of rape (B. campestris) was 75.6% at 100 mg/L (the activity level was B grade).

Key words: camphoric acid, acylhydrazone, synthesis, antibacterial activity, herbicidal activity

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