Metabolism of 3′,4′-Dichloropropionanilide: 3,4-Dichloroaniline-Lignin Complex in Rice Plants

Abstract

Rice plants (Oryza sativa L. var. Bluebonnet 50) metabolize the herbicide 3',4'-dichloropropionanilide to 3,4-dichloroaniline, which in turn conjugates with carbohydrates. Soluble aniline-carbohydrate complexes account for only a small fraction of the hydrolyzed 3',4'-dichloropropionanilide. The major portion of the 3,4-dichloroaniline moiety is found complexed with polymeric cell constituents, mainly lignin. The aniline is lignin-bound as 3,4-dichloroaniline and not as 3',4'-dichloropropionanilide.

Resistance Mechanism of Propanil-Resistant Barnyardgrass: II. In-vivo Metabolism of the Propanil Molecule

“…Although we did not positively identify these metabolites via structural analysis, other researchers studying propanil metabolism in rice using the pyridine ] n-butanol ] water solvent system10 have identiÐed metabolites with similar R f values as 3,4-dichlorophenyl-glucosylamine (R f \ 0É78) and a 3,4-dichlorophenyl-saccharide conjugate (R f \ 0É60). 10,12,13,21 It is likely that the metabolites recovered in our studies are the same conjugates, since they were present in both rice and propanil-resistant barnyardgrass, and similar values were obtained using R f these two solvent systems. These conclusions are supported by the higher level of non-extractable 14C in rice and propanil-resistant barnyardgrass.…”

Pesticide Conjugates-Glycosides

“…Propanil metabolism studies in rice (22,32), however, suggest that the N-glucoside of 3,4-dichloroaniline may undergo further metabolic reactions to yield other glycosides and a methanol-insoluble "lignin" complex.…”

Isolation and identification of three unreported carbon-14-labeled photodieldrin metabolites in soil

“…Such residues have been reported for different chemical classes, especially for fungicides or herbicides containing N (Chin et al, 1973;Yih et al, 1968;Bakke et al, 1972), but also for metabolites of organochlorines (Klein et al, 1973;Kilzer et al, 1974). The complex-forming substances were lignins in the case of plants (Chin et al, 1973;Yih et al, 1968); in the case of soil, humic acids seem to be complex formers. The bound residues are released when the complex is destroyed; for soil, alkali has been successful in some cases (Klein et al, 1973;Kilzer et al, 1974).…”