Ozonides and epoxides from ozonization of pyrethroids

Journal Article · · J. Agric. Food Chem.; (United States)

DOI:https://doi.org/10.1021/jf00072a002· OSTI ID:6692390

Ruzo, L O; Kimmel, E C; Casida, J E

Ozonization of pyrethroids as solutions or thin films yields products proposed to be epoxides from the 2,2-dihalovinyl substituents of deltamethrin and permethrin and transitory ozonides from these compounds and more stable ozonides from the 2-methyl-1-propenyl and 2-chloro-3,3,3-trifluoropropenyl substituents of phenothrin and descyanocyhalothrin, respectively. The unstable epoxydeltamethrin from ozonization is identified by /sup 1/H nuclear magnetic resonance spectroscopy and chemical ionization-mass spectroscopy and by reversion to deltamethrin on treatment of reaction mixtures with triphenylphosphine. Degradation of the ozonides yields the corresponding caronaldehyde in each case and trifluoroacetyl chloride from the chlorotrifluoropropenyl analogues. The ozonolysis mixtures are direct acting but weak bacterial mutagens presumable due to their epoxide and ozonide components.

• Research Organization: Univ. of California, Berkeley
• OSTI ID: 6692390
• Journal Information: J. Agric. Food Chem.; (United States), Journal Name: J. Agric. Food Chem.; (United States) Vol. 34:6; ISSN JAFCA
• Country of Publication: United States
• Language: English

Related Subjects

500200 -- Environment
Atmospheric-- Chemicals Monitoring & Transport-- (-1989)
54 ENVIRONMENTAL SCIENCES
560300* -- Chemicals Metabolism & Toxicology
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
BACTERIA
CHEMICAL REACTIONS
EPOXIDES
INSECTICIDES
MAGNETIC RESONANCE
MASS SPECTROSCOPY
MICROORGANISMS
MUTAGENESIS
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OZONIZATION
PESTICIDES
RESONANCE
SPECTROSCOPY