Abstract
The photoisomerization kinetics of trifloxystrobin (TFS) in acetone under artificial sunlight is reported. HPLC analysis showed the TFS, a strobilurine fungicide of EE conformation, was converted into an equilibrium mixture of four isomers after illumination for 7 h. The isomers were identified as EZ, EE, ZZ, and ZE and were separated in the crystalline form by preparative HPLC and characterized by use of a variety of spectroscopic techniques. The quantum yield and reaction constants for the isomerization reactions were determined. The detailed spectral features of the individual isomers measured by UV, IR, Raman, NMR and mass spectroscopy are presented and compared. The spectra of the isomers were found to be very characteristic, with good analytical significance.
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Häuser-Hahn I, Pontzen R, Baur P (2003) Mode of action of Flint WG 50: Analysis of spray deposit, rain fastness, and systemic properties on apple seedlings. Pflanzenschutz-Nachrichten Bayer 56:246–258
Ziegler H, Benet-Buchholz J, Etzel W, Gayer H (2003) Trifloxystrobin—a new strobilurin fungicide with outstanding biological activity. Pflanzenschutz-Nachrichten Bayer 56:213–230
Reuveni M (2000) Efficacy of trifloxystrobin (Flint), a new strobilurin fungicide, in controlling powdery mildews on apple, mango and nectarine, and rust on prune trees. Crop Prot 19(5):335–341
Reuveni M (2001) Activity of trifloxystrobin against powdery and downy mildew diseases of grapevines. Can J Plant Pathol 23(1):52–59
Ebeling M, Heimann KG, Schoefer S, Sonder K (2003) The human and environmental safety aspects of trifloxystrobin. Pflanzenschutz-Nachrichten Bayer 56:231–245
Banerjee K, Ligon AP, Schürmann M, Preut H, Spiteller M (2004) Methyl (Z, Z)-α-(methoxyimino)-2-[({1-[3-(trifluoromethyl)phenyl]ethylidene}amino) oxymethyl] benzeneacetate. Acta Cryst E60:525–526
Banerjee K, Ligon AP, Schürmann M, Preut H, Spiteller M (2004) Methyl (E,Z)-α-(methoxyimino)-2-[({1-[3-(trifluoromethyl)phenyl]ethylidene}amino) oxymethyl] benzeneacetate. Acta Cryst E61:o1752–o1753
Banerjee K, Ligon AP, Schürmann M, Preut H, Spiteller M (2004) Methyl (Z, E)-α-(methoxyimino)-2-[({1-[3-(trifluoromethyl)phenyl]ethylidene}amino) oxymethyl] benzeneacetate Acta Cryst E61:o1569–o1570
Steinemann A (1996) Fungitoxic acitvity of CGA 279202 isomers and metabolites in vitro. Bayer CropScience AG, unpublished report No. 96001PO
Giradet M (1997) Activity of CGA 279202 and CGA 321113 on Botrytis cinerea respiration. Bayer CropScience AG, unpublished report No. 08G 97010 BO
Braun AM, Marie-Therese Maurette, Oliveros E (1991) Photochemical Technology, Wiley, Chichester, UK, pp 70–106
Hatchard CG, Parker CA (1956) A new sensitive chemical actinometer II. Potassium ferrioxylate as a standard chemical actinometer. Proc R Soc Lond Sec A 235:518–536
Powersim Studio 2003, Version 5.1, Powersim Software AS, Bergen—Norway
Lang L (1962) Absortion spectra in the ultraviolet and visible region. In: Lang L (ed) Academic Press, NY, USA, pp 3022–3023
Gaussian 03, Revision A.1,Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, BaroneV, Mennucci B, Cossi M, ScalmaniV, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian Inc., Pittsburgh PA, USA
Acknowledgements
The authors thank the Ministry of Science and Technology, Government of India for awarding a BOYSCAST fellowship to Kaushik Banerjee. Thanks are also due to Bayer CropScience AG, Monheim, Germany, for providing reference standards, technical suggestions, and literature support.
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Banerjee, K., Ligon, A.P. & Spiteller, M. Photoisomerization kinetics of trifloxystrobin. Anal Bioanal Chem 382, 1527–1533 (2005). https://doi.org/10.1007/s00216-005-3336-8
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DOI: https://doi.org/10.1007/s00216-005-3336-8