Alteration of Diphenamid Metabolism in Tomato by Ozone

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Abstract
Fumigation of tomato (Lycopersicon esculentumMill. ‘Sheyenne’) with low levels of O3had little effect on root absorption, translocation, or conversion of diphenamid (N,N-dimethyl-2,2-diphenylacetamide) to water-soluble conjugates. However, the proportion of specific conjugates was markedly altered in O3-fumigated plants. Twenty-four hours after treatment, the predominant conjugates formed in nonfumigated and fumigated tomato were the β-glucoside (MDAG), and the β-gentiobioside (MDAGB), respectively, ofN-hydroxymethyl-N-methyl-2,2-diphenylacetamide. The ratio MDAG:MDAGB was 8.2:1.0 in nonfumigated tissue and 0.6:1.0 in O3-fumigated tissue. This marked shift toward production of the more polar MDAGB was accompanied by a trend toward increased production of methanol-insoluble residues. A compound having limited stability was extracted from tomato; its probable structure wasN-hydroxymethyl-N-methyl-2,2-diphenylacetamide (MODA). It is a postulated intermediate in the formation of MDAG and MDAGB from diphenamid.

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