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 compound
2 with hydrazine hydrate. And then, 12 novel camphoric acid-based acylhydrazone compounds
4a-
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. Compound
4i 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).