Identification of Insecticide Photoproducts by Mass Spectrometry
Mirex (dodecachloropentacyclo[5.3.0.02,6.03,9.04,8]decane), 1, has been used extensively in the southeastern United States to control the imported fire ants (Solenopsis invicta and Solenopsis richteri). The irradiation of this chlorocarbon in hydrocarbon solvents with ultraviolet light produced C10C111H and C10C110H2 derivatives (Alley et a1., 1973). Three isomers are possible, 2, 3, and 4. The infrared spectrum of the C10C111H photoproduct differed from that reported by Dilling et al. (1967) for 1,2,3,4,5,5,6,7,8,9,10-undecachloro[5.3.0.02,6, .03,9.04,8]decane (2). Nothing was known about the chemical reactivity of the different chlorine atoms in Mirex; therefore, synthesis of compounds with known structures was not possible. Furthermore, neither infrared, mass spectral, nor nmr data provided any information to help establish which of the remaining isomers (3 or 4) was the photoproduct.
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