caa a22 4500 469042095 CHVBK 20180323132814.0 cr unu---uuuuu 170328e19920501xx s 000 0 eng 10.1007/BF01974379 doi (NATIONALLICENCE)springer-10.1007/BF01974379 Metabolism of imazalil by wild-type and DMI-resistant isolates of Penicillium italicum [Elektronische Daten] [J. Guan, L. Van Leemput, M. Posthumus, M. De Waard] Metabolism of imazalil (1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole) inPenicillium italicum isolates with a wild-type sensitivity and with various degrees of resistance to sterol demethylation inhibitors was studied in liquid cultures. The metabolite 1-[2(2,4-dichlorophenyl)-2-(2,3-dihydroxypropyloxy)ethyl]-1H-imidazole (R42243) was detected in the culture filtrate after prolonged incubation. The metabolism occurred in the propenyl side chain of imazalil probably through epoxidation and hydratation. This is the first report of such a conversion of imazalil in fungi. R42243 was much less toxic toP. italicum than imazalil. Therefore, the metabolism can be regarded as a detoxification step. Both wild-type and resistant isolates metabolized imazalil, but metabolism by resistant isolates was faster than by the wild-type isolate. This is probably caused by a relatively strong inhibition of growth of the wild-type isolate by the fungicide. Results indicate that the detoxification of imazalil does not operate as a mechanism of resistance. This conclusion was confirmed by the fact that resistant isolates showed cross-resistance to miconazole and R42243, which had a similar structure as imazalil except for the propenyl side chain. Koninklijke Nederlandse Planteziektenkundige Vereniging, 1992 DMIs nationallicence detoxification nationallicence mechanism of resistance nationallicence metabolism nationallicence miconazole nationallicence Guan J. Department of Phytopathology, Wageningen Agricultural University, P.O. Box 8025, 6700 EE, Wageningen, the Netherlands aut Van Leemput L. Janssen Pharmaceutica, Turnhoutsweg 30, B-2340, Beerse, Belgium aut Posthumus M. Department of Organic Chemistry, Wageningen Agricultural University, P.O. Box 8026, 6700 EG, Wageningen, the Netherlands aut De Waard M. Department of Phytopathology, Wageningen Agricultural University, P.O. Box 8025, 6700 EE, Wageningen, the Netherlands aut Netherlands Journal of Plant Pathology Kluwer Academic Publishers 98/3(1992-05-01), 161-168 0028-2944 98:3<161 1992 98 10658 https://doi.org/10.1007/BF01974379 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF01974379 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Guan J. Department of Phytopathology, Wageningen Agricultural University, P.O. Box 8025, 6700 EE, Wageningen, the Netherlands aut NATIONALLICENCE 700 1- Van Leemput L. Janssen Pharmaceutica, Turnhoutsweg 30, B-2340, Beerse, Belgium aut NATIONALLICENCE 700 1- Posthumus M. Department of Organic Chemistry, Wageningen Agricultural University, P.O. Box 8026, 6700 EG, Wageningen, the Netherlands aut NATIONALLICENCE 700 1- De Waard M. Department of Phytopathology, Wageningen Agricultural University, P.O. Box 8025, 6700 EE, Wageningen, the Netherlands aut NATIONALLICENCE 773 0- Netherlands Journal of Plant Pathology Kluwer Academic Publishers 98/3(1992-05-01), 161-168 0028-2944 98:3<161 1992 98 10658 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer