Ozonides and epoxides from ozonization of pyrethroids
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), Vol. 34:6
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
54 ENVIRONMENTAL SCIENCES
EPOXIDES
MUTAGENESIS
INSECTICIDES
OZONIZATION
BACTERIA
MASS SPECTROSCOPY
NUCLEAR MAGNETIC RESONANCE
CHEMICAL REACTIONS
MAGNETIC RESONANCE
MICROORGANISMS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PESTICIDES
RESONANCE
SPECTROSCOPY
560300* - Chemicals Metabolism & Toxicology
500200 - Environment
Atmospheric- Chemicals Monitoring & Transport- (-1989)