Photoinduced addition of the fungicide anilazine to cyclohexene and methyloleate as model compounds of plant cuticle constituents

Citation
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
Citations number
4
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Environment/Ecology
Journal title
CHEMOSPHERE
ISSN journal
0045-6535 → ACNP
Volume
41
Issue
9
Year of publication
2000
Pages
1401 - 1406
Database
ISI
SICI code
0045-6535(200011)41:9<1401:PAOTFA>2.0.ZU;2-3
Abstract
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.