De. Breithaupt et W. Schwack, Photoinduced addition of the fungicide anilazine to cyclohexene and methyloleate as model compounds of plant cuticle constituents, CHEMOSPHERE, 41(9), 2000, pp. 1401-1406
Photoreactions, initiated by sunlight irradiation, between organochlorine p
esticides and olefinic compounds of plant cuticles have been postulated. Co
ncerning the formation of bound residues, which so far have not been detect
able by common analytical techniques, photoaddition reactions are of main i
nterest. In order to study the photochemical behavior of chlorinated fungic
ides, anilazine was irradiated in cyclohexene and methyl oleate as model co
mpounds for olefinic plant cuticle constituents. Anilazine extensively reac
ted with the cis-double bond of both model compounds via radical mechanisms
. In addition to a dechlorinated photoproduct several addition products wer
e formed showing plausible reaction pathways for the formation of bound res
idues in plant cuticles. Photoproducts were isolated by preparative HPLC an
d analyzed by HPLC, MS,H-1-, and C-13-NMR. (C) 2000 Elsevier Science Ltd. A
ll rights reserved.