Metabolism of 3‐chloro‐4‐methoxyaniline and some <i>N</i>‐acyl derivatives in soil

Briggs, G. G.; Ogilvie, Susan

doi:10.1002/ps.2780020408

Cited by 16 publications

(14 citation statements)

References 11 publications

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“…We were unable to detect an azobenzene or other oxidation product of DCPD similar to that which has been reported for 3,4-dichloroaniline, a metabolite of the herbicide 3,4-dichloropropionanilide (propanil) (Bartha and Pramer, 1970) and for 3-chloro-4-methoxyaniline (Briggs and Ogilvie, 1971). Tweedy et al (1970a,b) also failed to detect azobenzene formation from metobromuron.…”

Section: Resultssupporting

confidence: 64%

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Microbial metabolism of the fungicide 2,6-dichloro-4-nitroaniline

Alfen¹,

Kosuge²

1974

J. Agric. Food Chem.

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Section: Resultssupporting

confidence: 64%

“…Tweedy et al (1970a,b) also failed to detect azobenzene formation from metobromuron. However, their experiments as well as ours were carried out under conditions quite different from these reported by Bartha andPramer (1970) andbv Briggs andOgilvie (1971).…”

Section: Resultsmentioning

confidence: 73%

Microbial metabolism of the fungicide 2,6-dichloro-4-nitroaniline

Alfen¹,

Kosuge²

1974

J. Agric. Food Chem.

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“…The mechanism of the oxidative oligomerization of chloroanilines by oxidoreductases has been studied by some authors, who suggested reaction schemes consistent with one-electron oxidation, followed by a freeradical coupling reaction (Briggs and Ogilvie, 1971;Bordeleau et al, 1972;Iwan et al, 1976;Simmons et al, 1987).…”

Section: Discussionmentioning

confidence: 99%

Oxidation of Chloroanilines at Metal Oxide Surfaces

Pizzigallo

Ruggiero

Crecchio

et al. 1998

J. Agric. Food Chem.

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The oxidation reaction of chlorinated anilines by two manganese oxides, birnessite and pyrolusite, and by iron oxide has been investigated. The oxidation ability of the oxides was in the order birnessite . pyrolusite > iron oxide. Birnessite removed 100% of chloroanilines in 30 min, whereas pyrolusite and iron oxide removed from 5 to 96% of chloroanilines in 72 h. The differences in the reactivity of chloroanilines depended on the number and the position of chloro substituents on the aromatic ring. The activity of the oxides was maximal at pH 4.0 and decreased as the pH increased. The reaction kinetics in each of the systems investigated was adequately described by a secondorder rate expression. A free-radical mechanism for the oxidative coupling reaction of chlorinated anilines was suggested. Chloroazobenzene and chlorohydroxydiphenylamine dimers were detected among the oxidation products. The results obtained suggested that the oxidative mechanism occurred through a head-to-head and head-to-tail coupling of chloroanilino radicals.

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“…The initial stimulation in both CO, evolution and 0, uptake during the first 2 weeks is a common feature of all the substituted ureas examined and has also been demonstrated for many other herbicides.20*21 It is possible that moieties, containing carbon, released by chemical or enzymic degradation of the herbicide molecule may increase microbial activity. This is more likely with the more readily degradable metoxuron, 22 where potential for increased microbial activity is also suggested by the initial increase in 0, uptake in glucose-supplemented soils, and the rise in numbers of bacterial propagules at 500 parts/million a.i. This would explain why the increase did not occur at 50 parts/million a.i.…”

Section: Discussionmentioning

confidence: 96%

The effect of seven substituted urea herbicides on the soil microflora

Grossbard

Marsh

1974

Pestic. Sci.

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Chloroxuron, diuron, fluometuron, metobromuron and monuron added to soil at 500 parts/million a.i. on a dry weight basis caused an initial stimulation of COz production, followed by indications of inhibition. Nitrification was clearly inhibited, particularly by monuron and metobromuron.Metoxuron at 5 and 50 parts/million a.i. had no effect on CO, output and nitrification, but at 500 parts/million a.i. both were greatly reduced. Numbers of fungal propagules were temporarily lower at 50 parts/million a.i., and severely curtailed at 500 parts/million a.i. but total counts of bacterial propagules were greatly increased.Linuron had an inhibitory effect on CO, evolution at 500 parts/million a.i. but this varied in extent and duration; some reduction was also found at 50 parts/ million a.i. At 500 partslmillion a.i. there was no effect on mineralisation of N but in soil supplemented with ammonium sulphate nitrification was reduced. Changes in microbial equilibrium occurred, but were less marked than with metoxuron. Cellulose decomposition was also reduced. Small amounts of 3,4dichloroaniline were found in linuron-treated soils, but microbial activities were not affected when 5 parts/million 3,4-dichloroaniline was added to the soil. However, at 140 parts/million microbial activities were affected adversely, but in a different pattern to that for linuron; nitrification was severely reduced, but numbers of fungal propagules were hardly affected, suggesting that the effects observed in linuron-treated soil were not due to this metabolite.

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Metabolism of 3‐chloro‐4‐methoxyaniline and some N‐acyl derivatives in soil

Cited by 16 publications

References 11 publications

Microbial metabolism of the fungicide 2,6-dichloro-4-nitroaniline

Microbial metabolism of the fungicide 2,6-dichloro-4-nitroaniline

Oxidation of Chloroanilines at Metal Oxide Surfaces

The effect of seven substituted urea herbicides on the soil microflora

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