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Decomposition of Phenoxyalkyl Carboxylic Acids¹

ABSTRACT

The persistence of phenoxyalkyl carboxylic acids in soil was measured by a bioassay technique using alfalfa seedlings. Acetic, alpha-propionic and alpha- and gammabutyric acid derivatives were toxic when applied to soil planted to alfalfa whereas the beta-propionic acid derivatives showed no inhibition of the test plant. All 3,4-dichloro- and 2,4,5-trichlorophenoxyalkyl carboxylic acids exhibited prolonged persistence in soil. The duration of phytotoxicity in soil receiving 4-chloro-, 2,4-dichloro- and 2-methyl-4-chlorophenoxyalkyl carboxylic acids was governed by the type and linkage of the aliphatic side chain.

A Flavobacterium sp. active in the degradation of phenoxybutyric acids was isolated. The bacterium metabolized only phenoxybutyric acids having no meta chlorine on the aromatic ring. In the decomposition, the organic chlorine was liberated and the aromatic ring cleaved.

The results demonstrate that specific structural characteristics of these herbicide molecules govern persistence of the compounds in soil.

¹ Contribution from the Department of Agronomy, New York State College of Agriculture, Cornell University, Ithaca, N. Y. as Agronomy Paper No. 537. Research supported in part by Cooperative Regional Research Project NE-42.

² Chemical Analyst, Research Associate, and Associate Professor of Soil Science, respectively.

Received for publication June 30, 1961. Accepted for publication August 28, 1961.