Synthesis, controlled release properties, and increased antifungal activities of novel cis- and trans-racemate complexes of propiconazole.
Twenty novel metal complexes M(1)(cis-L)(2)Y(2), M(1)(trans-L)(2)Y(2,) M(2)(cis-L)(4)Y(2), and M(2)(trans-L)(4)Y(2) (M(1) = Zn(II), Co(II), Cu(II); M(2) = Mn(II), Ni(II); Y = OAc, Cl, ClO(4), and NO(3)) were synthesized by reacting bivalent transitional metal salt MY(2).nH(2)O (n = 0-6) with ligands cis-racemate of propiconazole (cis-L) and trans-racemate of propiconazole (trans-L), respectively. All of these synthesized complexes were identified by atomic absorption spectrometry, elemental analysis, and IR and UV spectra. The cumulative release studies of some selected complexes in static water were performed; all determined complexes were found to exhibit attractive controlled release properties, yet the ligand release rates of cis-L complexes were slower than those of trans-L complexes. Meanwhile, it was found that the release rate of ligand cis-L from representative complex Zn(cis-L)(2)Cl(2) was affected obviously by different conditions, such as temperature, pH, and PVA film coating. The antifungal activities of the ligands and their complexes against five selected plant pathogenic fungi were evaluated; the results demonstrated that the toxicity of cis-L was 3.39-5.95 times greater than that of trans-L, and all of the synthesized complexes showed superior activities of 1.19-6.36 times to those of their ligands, especially Zn complexes having toxicities 2.62-6.36 times greater than those of their ligands. Moreover, the cis-L complexes had more sensitive activities than their relevant trans-L complexes; for example, Zn(cis-L)(2)Cl(2) appeared to be 5.00-8.67 times stronger than Zn(trans-L)(2)Cl(2) complex. In addition, the mechanism of increased antifungal activities of the title complexes in comparison with their ligands was discussed preliminarily.
Chen
Xi
X
College of Science, Nanjing Agricultural University, Nanjing, People's Republic of China.
Yang
Chunlong
C
D003692:Delayed-Action Preparations; D005659:Fungicides, Industrial / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000494:pharmacology*; D007536:Isomerism; D008670:Metals / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry* / Q000494:pharmacology
D003692:Delayed-Action Preparations; D005659:Fungicides, Industrial; D008670:Metals; D014230:Triazoles; C045950:propiconazole