Spectrochimica Acta Part A 53 (1997) 2679 – 2684
UV-visible absorption spectra and luminescence of the pesticide
fenarimol
M. Conceic ¸a ˜o
b
, D.A. Mateus
a,
*, Abı ´lio M. da Silva
a
, Hugh D. Burrows
b
a
UCEH, Uniersidade do Algare 8000 Faro, Portugal
b
Departamento de Quı ´mica, Uniersidade de Coimbra, 3049 Coimbra, Portugal
Received 28 April 1997; received in revised form 6 June 1997; accepted 26 June 1997
Abstract
The UV-visible absorption and emission spectra have been measured of the pesticide fenarimol (( )-2,4-dichloro-
-(pyrimidin-5-yl)-benzhydryl alcohol) in solution. From comparison with the spectra of chlorotoluenes and pyrim-
idine, and from the effect of solvent polarity on the absorption spectrum, it is shown that the lowest excited singlet
state is localized on the pyrimidine ring, and has n, * character. Higher excited , * states are localized on both
chlorotoluene and pyrimidine rings. Fenarimol shows a weak, fluorescence from the n, * state, with a quantum yield
which is strongly dependent on solvent. It is shown that this is due to changes in the nonradiative decay rate,
particularly in protic solvents, due to increased intersystem crossing. Phosphorescence is observed in low temperature
glasses. Although this shows two decay components, it is suggested that only one triplet state is involved, and that
this has predominantly , * character. © 1997 Elsevier Science B.V.
Keywords: Luminescence; Pesticide fenarimol; UV-visible absorption
1. Introduction
The fungicide fenarimol (( )-2,4-dichloro- -
(pyrimidin-5-yl)benzhydryl alcohol, I) is exten-
sively used for spraying fruit and ornamental
plants [1]. However, in spite of its widespread use,
spectroscopic data on this compound is rather
limited. The compound is photochemically un-
stable, and is readily broken down by sunlight [1].
In a previous report [2] we presented some prelim-
inary data on the spectral and photophysical prop-
erties of this compound, together with tentative
assignments of the photogradation products. We
suggested that photodegradation probably pro-
ceeds through the lowest excited singlet state, and
that this has predominantly n, * character. To
obtain further information on the excited elec-
tronic states of fenarimol we have carried out more
detailed spectroscopic and photophysical studies,
with particular interest in the effect of solvent.
* Corresponding author. Fax: +351 89 818560; e-mail:
mcmateus@mozart.si.ualg.pt
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