Hydrolysis of 2,6-dichlorobenzonitrile in soils

Briggs, G. G.; Dawson, J. E.

doi:10.1021/jf60167a030

Cited by 32 publications

(15 citation statements)

References 4 publications

(5 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Verloop &Nimmo (1970) andBrigg? &Dawson (1970) have found that dichlobenil (2,6-dichlorobcnzonitrilc) is slowly liydrolysed in soil to 2,6dichlorobenzamide. Whether this hydrolysis is microbial or chemical in origin seems to be in some doubt, as the Dutch group observed very little hydrolysis of dichlobenil in sterile soil over a 6-month period, whereas the results of the American investigators indicated hydrolysis in both sterile and non-sterile soils.…”

Section: Resultsmentioning

confidence: 99%

Degradation of Bromoxynil in Regina Heavy Clay*

Smith

1971

Weed Research

View full text Add to dashboard Cite

Summary A spectrophotometric method was developed to detect bromoxynil in Regina heavy clay, and the breakdown under different temperature and moisture conditions was studied. At rates equivalent to 14 kg/ha, over 50% of the applied bromoxynil was degraded in 2 weeks at 25°C and at moisture levels in excess of the wilting point. Losses at 18°C were slightly slower. Little breakdown occurred in sterile soil, indicating that microbial degradation could be an important factor contributing to bromoxynil breakdown under field conditions. Paper and thin‐layer chromatographic techniques were used to isolate and identify soil degradation products. In addition to the parent compound small amounts of 3,5‐dibromo‐4‐hydroxybenzamide and 3,5‐dibromo‐4‐hydroxybenzoic acid were detected.

show abstract

Section: Resultsmentioning

confidence: 99%

Degradation of Bromoxynil in Regina Heavy Clay*

Smith

1971

Weed Research

View full text Add to dashboard Cite

show abstract

“…Halogenated benzonitriles have been found to undergo microbial conversion of the cyano group [179]. 2,6-Dichlorobenzonitrile was shown to be converted to 2,6-dichlorobenzamide in aerobic soils [364]. Halogenated benzoic acids have also been suggested as metabolites of halobenzonitriles [179].…”

Section: Anaerobic Dehalogenation Of Phenylamide Pesticides and Anilinesmentioning

confidence: 99%

Microbial breakdown of halogenated aromatic pesticides and related compounds

Häggblom

1992

FEMS Microbiology Letters

363

132

View full text Add to dashboard Cite

Considerable progress has been made in the last few years in understanding the mechanisms of microbial degradation of halogenated aromatic compounds. Much is already known about the degradation mechanisms under aerobic conditions, and metabolism under anaerobiosis has lately received increasing attention. The removal of the halogen substituent is a key step in degradation of halogenated aromatics. This may occur as an initial step via reductive, hydrolytic or oxygenolytic mechanisms, or after cleavage of the aromatic ring at a later stage of metabolism. In addition to degradation, several biotransformation reactions, such as methylation and polymerization, may take place and produce more toxic or recalcitrant metabolites. Studies with pure bacterial and fungal cultures have given detailed information on the biodegradation pathways of several halogenated aromatic compounds. Several of the key enzymes have been purified or studied in cell extracts, and there is an increasing understanding of the organization and regulation of the genes involved in haloaromatic degradation. This review will focus on the biodegradation and biotransformation pathways that have been established for halogenated phenols, phenoxyalkanoic acids, benzoic acids, benzenes, anilines and structurally related halogenated aromatic pesticides. There is a growing interest in developing microbiological methods for clean‐up of soil and water contaminated with halogenated aromatic compounds.

show abstract

“…There are, however, only a few published studies on the sorption of dichlobenil (7)(8)(9) and of BAM (10,11). Dichlobenil was only studied in topsoils with a high organic carbon content and with concentrations in milligrams per liter range.…”

Section: Introductionmentioning

confidence: 99%

Sorption of the Herbicide Dichlobenil and the Metabolite 2,6-Dichlorobenzamide on Soils and Aquifer Sediments

Clausen

Larsen

Albrechtsen

2004

Environ. Sci. Technol.

View full text Add to dashboard Cite

The worldwide used herbicide dichlobenil (2,6-dichlorobenzonitrile) has resulted in widespread presence of its metabolite 2,6-dichlorobenzamide (BAM) in pore- and groundwater. To evaluate the transport of these compounds we studied the sorption of dichlobenil and BAM in 22 sediment samples of clayey till, sand, and limestone including sediments exhibiting varying oxidation states. Dichlobenil sorbed to all investigated sediments, with a high sorption in topsoils (Kd = 7.4-17.4 L kg(-1)) and clayey till sediments (Kd = 2.7-126 L kg(-1)). The sorption of the polar metabolite BAM was much lower than the sorption of dichlobenil but followed the same tendency with the highest sorption in the topsoils (Kd = 0.24-0.66 L kg(-1)) and in the clayey till sediments (Kd = 0.10-0.93 L kg(-1)). The sorption of both compounds was significantly higher (2-47 times) in the unoxidized (reduced) clayey till than in the weathered (oxidized) clayey till. Such a difference in sorption capacity could neither be explained by a higher organic carbon content, sorption to clay minerals, differences in clay mineralogy, nor by blocking of reactive surface sites on clay minerals by iron oxides. However, by removing an average of 81% of the organic carbon from the reduced clayey till with H2O2, the sorption decreased on average 50%. Therefore, most of the sorption capacity in the reduced clayey till was related to organic carbon, which indicates that sorption processes are affected by changes in organic compound composition due to weathering.

show abstract

Hydrolysis of 2,6-dichlorobenzonitrile in soils

Cited by 32 publications

References 4 publications

Degradation of Bromoxynil in Regina Heavy Clay*

Degradation of Bromoxynil in Regina Heavy Clay*

Microbial breakdown of halogenated aromatic pesticides and related compounds

Sorption of the Herbicide Dichlobenil and the Metabolite 2,6-Dichlorobenzamide on Soils and Aquifer Sediments

Contact Info

Product

Resources

About