Atrazine Metabolism by Nocardia: Elucidation of Initial Pathway and Synthesis of Potential Metabolites

Giardina, M. C.; Giardi, Maria Teresa; Filacchioni, Guido

doi:10.1080/00021369.1982.10865301

Cited by 30 publications

(29 citation statements)

References 3 publications

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“…Foster et al (1980) observed not only dechlorination of CEAT in soluble extracts from liver preparations but also apparent spontaneous hydrolysis of the chloro substituent, though the latter could be an artifact (Dauterman and Muecke, 1974). Giardina et al (1982) also reported spontaneous decay of CEAT at an unknown low concentration, and they identified a product that is presumed to arise from a microbial reaction at the level of the (alky1)amino ring substituent.…”

Section: Resultsmentioning

confidence: 99%

“…We suspect that their clean up, which involves an acidic alumina column, may be the source of the discrepancy, and Dauterman and Muecke (1974) warn against similar artifacts. Giardina et al (1982) also believe CEAT to be unstable, but they describe an unquantified, chlorinated product, which is presumably formed from CEAT many unidentified products are also claimed. Fungal dechlorination of atrazine ( C E T ) has been claimed in an unverified report in which the behavior of the controls is not described (Couch et al, 1965).…”

Section: Resultsmentioning

confidence: 99%

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Deethylsimazine: bacterial dechlorination, deamination, and complete degradation

Cook¹,

Hütter²

1984

J. Agric. Food Chem.

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Enrichment cultures utilizing deethylsimazine (6-chloro-N-ethyl-l,3,5-triazine-2,4-diamine) as a sole nitrogen source were obtained from so5 that had had long exposure to s-triazine herbicides. A bacterium was isolated that utilized deethylsimazine quantitatively as a nitrogen source for growth, but only 1 mol of nitrogen was obtained/mol of deethylsimazine, whereas all six atoms in melamine were utilized.The bacterium, which was identified as a strain of Rhodococcus corallinus, converted deethylsimazine to 1 mol of 6-(ethylamino)-l,3,5-triazine-2,4(1H,3H)-dione, 1 mol of chloride ion, and 1 mol of ammonium ion. 4-AminoS-(ethylamino)-l,3,5-triazin-2(~-one was tentatively identified as a transient intermediate in the degradation, which was presumed to be due to a dechlorination followed by a deamination. Growth of R. corallinus together with Pseudomonas sp. strain NRRL B-12228, which utilized 6-(ethylamino)-1,3,5-triazine-2,4( 1H,3H)-dione, resulted in complete conversion of deethylsimazine nitrogen to cell material.Deethylsimazine (6-chloro-N-ethyl-l,3,5-triazine-2,4-diamine; CEAT, see Table I and Figure 2) is the first compound to be conclusively identified as a microbial (fungal) product from a chloro-s-triazine herbicide [Kaufman et al., 1965; Kearney et al., 1965; see also Kaufman and Blake (1970)l. The product is formed in about 70% yield, the other 30% being an unidentified product, traces of ammelide (OOAT) have been tentatively

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Deethylsimazine: bacterial dechlorination, deamination, and complete degradation

Cook¹,

Hütter²

1984

J. Agric. Food Chem.

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“…In our study side chain degradation of atrazine or 2,4-D may have occurred, but was undetected because we measured the amount of atrazine and 2,4-D degraded to CO 2 . The degradation pathways of atrazine and 2,4-D are well known (Giardina et al 1982;Chaudhry and Chapalamadugu 1991). Atrazine and 2,4-D could have been degraded to a variety of intermediate compounds.…”

Section: Discussionmentioning

confidence: 99%

Influence of nitrogen on atrazine and 2, 4 dichlorophenoxyacetic acid mineralization in blackwater and redwater forested wetland soils

Entry¹

1999

Biology and Fertility of Soils

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Microcosms were used to determine the influence of N additions on active bacterial and fungal biomass, atrazine and dichlorophenoxyacetic acid (2,4-D) mineralization at 5, 10 and 15 weeks in soils from blackwater and redwater wetland forest ecosystems in the northern Florida Panhandle. Active bacterial and fungal biomass was determined by staining techniques combined with direct microscopy. Atrazine and 2,4-D mineralization were measured radiometrically. Treatments were: soil type, (blackwater or redwater forested wetland soils) and N additions (soils amended with the equivalent of 0, 200 or 400 kg N ha" as NH 4NO3). Redwater soils contained higher concentrations of C, total N, P, K, Ca, Mn, Fe, B and Zn than blackwater soils. After N addition and 15 weeks of incubation, active bacterial biomass in redwater soils was lower when N was added. Active bacterial biomass in blackwater soils was lower when 400 kg N ha-1 , but not when 200 kg N ha', was added. Active fungal biomass in blackwater soils was higher when 400 kg N ha-1 , but not when 200 kg N ha', was added. Active fungal biomass in redwater soils was lower when 200 kg N ha-1 , but not when 400 kg N ha', was added. After 15 weeks of incubation 2,4-D degradation was higher in redwater wetland soils than in blackwater soils. After 10 and 15 weeks of incubation the addition of 200 or 400 kg N ha' decreased both atrazine and 2,4-D degradation in redwater soils. The addition of 400 kg N ha' decreased 2,4-D degradation but not atrazine degradation in blackwater soils after 10 and 15 weeks of incubation. High concentrations of N in surface runoff and groundwater resulting from agricultural operations may have resulted in the accumulation of N in many wetland soils. Large amounts of N accumulating in wetlands may decrease mineralization of toxic agricultural pesticides.

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“…Whereas we now [92] suspect a larger series of converging catabolic pathways (Fig. 6) resulting from hydrolytic reactions at the s-triazine nucleus, Giardini's group [83,84,131] has evidence of a totally different mechanism of removal of a substituent from the s-triazine ring (Fig. 4B).…”

Section: Other Reactionsmentioning

confidence: 99%

Biodegration of s-triazine xenobiotics

Cook

1987

FEMS Microbiology Letters

206

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SUMMARYBiodegradation of xenobiotic compounds is examined with s-triazines as an example and with biological treatment of wastewater containing striazines as an aim. s-Triazines have been termed recalcitrant, but examination of the literature indicates that a potential for biodegradation exists. Nitrogen-limited enrichment cultures yield organisms able to degrade by-products of the industrial synthesis of s-triazine herbicides as sources of nitrogen. The choice of inoculum for these enrichments is important and often allows for successful enrichment after simple batch culture, but organisms containing several degradative reactions could be obtained only after selection in extended culture. Routine, specific determinations of all s-triazines (by HPLC) were essential throughout the work. Molar growth yields show complete mass balances for the utilization of s-triazines. Kinetic experiments indicate that specific degradation rates of s-triazines in growing cells are about 0.4 mkat/kg of protein. Characterised biochemical pathways consist of a series of hydrolytic cleavages of chloro-, amino-and alkylaminogroups from the s-triazine ring. Pathways con-

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Atrazine Metabolism by Nocardia: Elucidation of Initial Pathway and Synthesis of Potential Metabolites

Cited by 30 publications

References 3 publications

Deethylsimazine: bacterial dechlorination, deamination, and complete degradation

Deethylsimazine: bacterial dechlorination, deamination, and complete degradation

Influence of nitrogen on atrazine and 2, 4 dichlorophenoxyacetic acid mineralization in blackwater and redwater forested wetland soils

Biodegration of s-triazine xenobiotics

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