Fungicides and photochemistry: photodegradation of the azole fungicide penconazole.
In order to examine the photostability of the fungicide penconazole (1-(2,4-dichloro-beta-propylphenethyl)-1H-1,2,4-triazole, 1) in the field, model experiments with organic solvents were performed. Photodegradation (lambda > 280 nm) of penconazole was found to be more efficient in isopropanol and cyclohexane solution than in the presence of cyclohexene. Photolysis in isopropanol and cyclohexane resulted in considerable formation of 1-(4-chloro-beta-propylphenethyl)-1H-1,2,4-triazole (2) and 5H,6H-(1,2,4-triazolo)-[5,1-a]-9-chloro-6-propyl-isoquinoline (3). Furthermore, photodehalogenation of 3 yielded traces of 5H,6H-(1,2,4-triazolo)-[5,1-a]-6-propyl-isoquinoline (4) and, in the presence of isopropanol 5H,6H-(1,2,4-triazolo)-[5,1-a]-9-(2-hydroxy-2-methylethyl)-6-propyl- isoquioline (5). Additionally, a lot of polar products were found in high yields which could not be isolated and characterized individually. In the presence of cyclohexene, on the other hand, photodecomposition and photodehalogenation to photoproduct 2 were found to be the main degradation pathways and photoproduct 3 was only detected as a trace component.
Schwack
W
W
Institut für Lebensmittelchemie, Universität Karlsruhe, Germany.
Hartmann
M
M
D002851:Chromatography, High Pressure Liquid; D004355:Drug Stability; D005659:Fungicides, Industrial / Q000737:chemistry* / Q000528:radiation effects; D008401:Gas Chromatography-Mass Spectrometry; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010777:Photochemistry; D010782:Photolysis; D012997:Solvents; D013056:Spectrophotometry, Ultraviolet; D013997:Time Factors; D014230:Triazoles / Q000737:chemistry* / Q000528:radiation effects
D005659:Fungicides, Industrial; D012997:Solvents; D014230:Triazoles; C087058:penconazole