Studies related to the chemistry and environmental persistence of methoxychlor and its derivatives / by James Paul Vukmanich. --

An Investigation of some of the chemical and biological
\nfactors Influencing the environmental fate of methoxychlor
\n( 1 , 1, 1-trichloro-2,2-bis (p-methoxyphenyl) ethane) has been
\nconducted.
\nMethoxychlor is an organochlorine insecticide which
\nis used extensively in Canada and has been proposed as a
\npotential DDT replacement. It has been reported in the literature that methoxychlor exhibits a low toxicity towards most
\nmammals and is also partially degraded by these organisms.
\nAlthough much information exists on the interaction of this
\ninsecticide with higher animals, less information is available
\non the interaction between this compound and organisms at
\nlower tropic levels, especially the microorganisms. Methoxychlor, because of its use as a larviclde in and around natural water systems, has the potential to interact directly with nontarget
\naquatic biota. Therefore an investigation concerning
\nthe interaction between methoxychlor and aquatic microorganisms
\nwas initiated. The microorganisms chosen for this study were
\ncommon species of green algae, Chlorella pyrenoidosa and
\nChlorella vulgaris. The biological effects of methoxychlor
\nhave been studied in vitro using axenic cultures of the test
\nalgae .
\nKnown metabolites and derivatives of methoxychlor
\nrequired for this study were synthesized. The extensive modification of the literature methods for the preparation of
\nthese compounds has resulted in improved yields and purer products for virtually all compounds synthesized. The
\nsynthesis of 1-monochloro-2,2-bis (p-hydroxyphenyl) ethylene,
\na known methoxychlor metabolite, has been developed and
\nalmost completed. The synthesis of this compound has not
\nbeen reported in the literature before. The product of the
\npreviously reported base-promoted rearrangement of 1,1-dichloro-2,2-bis (p-hydroxyphenyl) ethane has been identified and
\na mechanism for its formation postulated.
\nAlso, to aid in the selection of solvents used for
\nthe extraction of the polar metabolites of methoxychlor from
\naqueous samples, the p-values (ie. extractability) and solubilities (in water and organic solvents) of these compounds have been determined.
\nThe toxicity of methoxychlor and hydroxychlor (1,1,1-
\ntrichloro-2,2-bis(p-hydroxyphenyl)ethane) towards both
\nspecies of algae was assessed. Although both species are
\ntolerant of relatively high concentrations of these compounds,
\nthe hydroxy analogue was much more toxic than the parent
\ninsecticide. Growth rate studies revealed that both methoxychlor and hydroxychlor had little effect on the overall growth
\nof Chlorella pyrenoidosa, The growth of Chlorella vulgaris
\nwas however, significantly depressed by methoxychlor, while
\non the other hand hydroxychlor stimulated the growth of this alga. Recovery experiments indicated that the uptake of
\nmethoxychlor and hydroxychlor by Chlorella pyrenoidosa is
\nmainly due to physical adsorption. In the case of Chlorella
\nvulgaris very little of the added methoxychlor could be recovered. Recovery experiments conducted with Chlorella vulgaris and hydroxychlor suggest that at least some of this compound is reductively dechlorinated by this organism.

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