The Metabolism of the Herbicide Diphenamid (N‐N‐dimethyl‐2,2‐diphenyl‐acetamide) in Cell Suspensions of Soybean (Glycine max)

Davis, David W.; Hodgson, Richard H.; Dusbabek, Kendall E.; Hoffer, Barry L.

doi:10.1111/j.1399-3054.1978.tb01619.x

Cited by 27 publications

(6 citation statements)

References 12 publications

(11 reference statements)

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“…The newly identified metabolite (14) is produced from hydrolysis of (3) and/or by decarboxylation of (15). Of three stepwise reductive metabolites resulting from a minor degradation reaction, (5) and (7) detected in the intact plant were also formed in this system. Phytotoxicity of fluoroimide and its metabolites was observed as an inhibition activity of the apple cell growth.…”

Section: Resultsmentioning

confidence: 90%

In Vitro Metabolism of Fluoroimide in the Cell Suspension of Apple Leaves

Ohori

Aizawa

1983

J. Pestic. Sci.

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In vitro metabolism of fluoroimide was studied in isolated apple cell suspension culture. The cells were isolated from freshly excised apple leaves by Macerozyme R-10, and cultured in Murashige-Skoog medium containing 1mg/l of 2, 4-D at 27°C in the dark. When 14C-fluoroimide (labeled at ethylene carbons) in DMSO solution was added to the cell suspension medium, fluoroimide was readily hydrolyzed and incorporated into the cells. The major metabolites were 4-fluoro-dichloromaleanilic acid (12), 2, 3-dichloromaleic acid (15) and (E)-2, 3-dichloroacrylic acid (14), and these were found both in the cell extracts and the medium. These In vitro metabolic profiles were similar to those of the intact Inu-apple tree, but in this study was identified (E)-2, 3-dichloroacrylic acid (14) by its isolation from massive cell culture of non-labeled fluoroimide. The growth inhibition activity of the apple cells was observed in fluoroimide and two kinds of dechlorinated metabolites (2 and 5) which were slightly produced.

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Section: Resultsmentioning

confidence: 90%

In Vitro Metabolism of Fluoroimide in the Cell Suspension of Apple Leaves

Ohori

Aizawa

1983

J. Pestic. Sci.

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“…Summarizing the results the conjugate was probably 6-0-malonyl-/l-Dglucoside of N-CH2OH-fenothiocarb. Formation of 6-0-malonyl-/l-D-glucoside in pesticide metabolism in plants has been studied by several researchers.7, [22][23][24][25][26][27][28] As shown in Fig. 3, there are other polar metabolites in the dichloromethane-soluble fraction of leaves, and the Rf values of these compounds were smaller than that of the 6-0malonyl-/l-D-glucoside of N-CH2OH-fenothiocarb.…”

Section: Metabolic Fate Of Fenothiocarbmentioning

confidence: 99%

Translocation and Metabolism of the Acaricide Fenothiocarb in Citrus

1986

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The translocation and metabolism of 14C-fenothiocarb [S-(4-[14C(U)] phenoxybutyl) N,N-dimethylthiocarbamate] were studied using citrus such as summer orange seedlings and mandarin orange trees with fruit under greenhouse conditions. Very little 14C-fenothiocarb was translocated when applied on the middle of upper or lower surface of leaf, and its limited translocation to an upward direction was found when applied to stem. When it was sprayed to mandarin orange trees, the initial concentration of radioactivity in the leaves and fruit rinds was 26.3 and 4.7 ppm, respectively. The radioactivity dissipated more rapidly in the leaves than in the rinds with the half-lives of fenothiocarb being estimated 1.6 and 12 days, respectively. The concentration of radioactivity in the edible part of fruit increased with time, but that equivalent to fenothiocarb remained 43 to 46 ppb at the mature stage. Orange juice from the edible part contained water-soluble metabolites. The major metabolites identified in the leaves, rinds and edible fruit were 6-0-malonyl-/3-D-glucoside of N-hydroxymethyl-fenothiocarb, N-formyl-fenothiocarb and glycoside conjugates of phenol, respectively. The minor ones were identified as fenothiocarb sulfoxide, N-hydroxymethyl-fenothiocarb, monodesmethyl-fenothiocarb and 4'-hydroxy-fenothiocarb.

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“…Indeed, the use of non-microbially-contaminated plant cell and tissue cultures has been prominent in providing definitive proof for the existence of ring-cleavage reactions within plants [81]. Culture systems can be extremely practicable for investigation ofxenobiotic metabolism since it has been proven that metabolites formed in culture are comparable to those in intact plants [122][123][124][125][126]. It must be remembered however, that under natural conditions, intact plants are subject to a range of environmental influences which can affect their capacity for metabolism ofxenobiotics.…”

Section: Specific Metabolism In Plantsmentioning

confidence: 99%