Synthesized Of Carabrone Derivatives And Their Antifugal Activities Research

Carabrone is isolated from many plants of carpesium species, it is a sesquiterpene lactone compound. The Research and Development Center of Biorational Pesticides studied that carabrone has high and broad-spectrum antifungal activity. Their researches of derivatives synthesis and antifungal activities found that the key antifungal activity structure of carabrone isα-methylene-γ-lactoney. In this thesis, we reserve the structure ofα-methylene-γ-lactone based on previous human studies, and mainly modified with C4-carbonyl of carabrone. We gained 14 carabrone derivatives, and measured their antifungal activities. Then we analysised the relationship between the derivatives structures and its antifungal activities.It was the main study conclusion as follows:1. 2 compounds of hydrazone derivatives Z1 and Z2 were synthesized by the modification of carabrone. Their chemical structure were confirmed by 1H NMR and 13C NMR, and were identified as new compounds.2. 12 compounds of ester derivatives S1-S11 and H1 were synthesized by the modification of carabrol. Their chemical structure were confirmed by 1H NMR and 13C NMR, and were identified as new compounds except S11.3. The antifungal activities of 14 derivatives were tested by hanging drop method. The EC50 of hydrazone derivatives Z1, Z2 and ester derivatives S9, S10, S11 were 11.17mg/L, 10.78mg/L, 7.74mg/L, 8.54mg/L and 4.21mg/L to Botrytis Cinerea; the EC50 of hydrazone derivatives Z1, Z2 and ester derivatives S7, S8, S9, S10, S11, H1 were 8.45mg/L, 9.51mg/L, 35.12mg/L, 34.55mg/L, 13.12mg/L, 31.12mg/L, 21.90mg/L and 15.62mg/L to Exserohilum turcicum; the EC50 of hydrazone derivatives Z1, Z2 and ester derivatives S7, S9, S10, S11, H1 were 6.41mg/L, 9.18mg/L, 18.27mg/L, 16.69mg/L, 8.53mg/L, 6.05mg/L and 14.75mg/L to Colletotrichum lagenarium. In summary, the antifungal activities of hydrazone derivatives was significantly increased. The EC50 of hydrazone derivatives Z1 and Z2 was 4-5 times lower than carabrone to Exserohilum turcicum. The antifungal activities of ester derivatives were different: benzoate and substituted benzoate were tiny changed; the EC50 of S10 and S11 were dropped obviously, their antifungal activity were significantly improved, and higher than carabrone; the EC50 of S7, S9 and H1 were different in different strains, their antifungal activity were higher than carabrol. The research shows, derivatives synthesis of carabrone can gain the higher antifungal activity compound: the hydrazone derivatives and N- heterocyclic ester derivatives have higher antifungal activity; the ester derivatives containing N, S elements can improved their antifungal activity.