Formation of a Methylthiolated Metabolite from the Fungicide Chlorothalonil by Soil Bacteria

Katayama, Arata; Ukai, Toshiaki; Nomura, Kazuyo; Kuwatsuka, Shozo

doi:10.1271/bbb.56.1520

Cited by 12 publications

(4 citation statements)

References 3 publications

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“…First, the high organic matter content may provide an ample carbon source for microorganisms responsible for the degradation of the two pesticides, and thus enhanced their degradation. Microbial transformation is the primary degradation mechanism for chlorothalonil (Sato and Tanaka, 1987; Rouchaud et al, 1988; Katayama et al, 1992) and pendimethalin (Kulshrestha and Singh, 1992; Scheunert et al, 1993). Accelerated microbial degradation has been reported for chlorothalonil in soils amended with farmyard manure (Mori et al, 1996).…”

Section: Resultsmentioning

confidence: 99%

Sorption and Degradation of Pesticides in Nursery Recycling Ponds

Newman³

et al. 2006

J of Env Quality

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Knowledge of pesticide distribution and persistence in nursery recycling pond water and sediment is critical for preventing phytotoxicity of pesticides during water reuse and to assess their impacts to the environment. In this study, sorption and degradation of four commonly used pesticides (diazinon, chlorpyrifos, chlorothalonil, and pendimethalin) in sediments from two nursery recycling ponds was investigated. Results showed that diazinon and chlorothalonil were moderately sorbed [K(OC) (soil organic carbon distribution coefficient) from 732 to 2.45 x 10(3) mL g(-1)] to the sediments, and their sorption was mainly attributable to organic matter content, whereas chlorpyrifos and pendimethalin were strongly sorbed (K(OC) > or = 7.43 x 10(3) mL g(-1)) to the sediments, and their sorption was related to both organic matter content and sediment texture. The persistence of diazinon and chlorpyrifos was moderate under aerobic conditions (half-lives = 8 to 32 d), and increased under anaerobic conditions (half-lives = 12 to 53 d). In contrast, chlorothalonil and pendimethalin were quickly degraded under aerobic conditions with half-lives < 2.8 d, and their degradation was further enhanced under anaerobic conditions (half-lives < 1.9 d). The strong sorption of chlorpyrifos and pendimethalin by the sediments suggests that the practice of recycling nursery runoff would effectively retain these compounds in the recycling pond, minimizing their offsite movement. The prolonged persistence of diazinon and chlorpyrifos, however, implies that incidental spills, such as overflows caused by storm events, may contribute significant loads of such pesticides into downstream surface water bodies.

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Section: Resultsmentioning

confidence: 99%

Sorption and Degradation of Pesticides in Nursery Recycling Ponds

Newman³

et al. 2006

J of Env Quality

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“…TPN metabolites degraded by these bacteria were identified to be TPN-OH (Liang et al 2010;Motonaga et al 1996) and methylthiotrichloroisophthalonitrile (Katayama et al 1997). These two products were considered to be derivatives of TPN with replacement of the chlorine atom at the 4-position (Katayama et al 1992(Katayama et al , 1997. However, detection of CCHT and DTTC in soil (Putnam et al 2003;Roberts and Hutson 1999;Rouchaud and Roucourt 1988) suggested the possibility of other metabolic pathways to degrade TPN by pure culture.…”

Section: Introductionmentioning

confidence: 99%

Chlorothalonil degradation by Ochrobactrum lupini strain TP-D1 and identification of its metabolites

Shi

Guo

Takagi

et al. 2010

World J Microbiol Biotechnol

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Chlorothalonil (2, 4, 5, 6-tetrachloroisophthalonitrile, TPN) has been widely used as a wide-spectrum fungicide in China and other countries, and is considered to be an important soil and water contaminant. Here we report the isolation and characterization of a novel TPN-degrading bacterial strain TP-D1 from a heavily TPN-polluted soil in Henan Province, China, and identified it as a strain of Ochrobactrum lupini based on 16S rRNA gene sequence analysis and its morphological, biochemical, and physiological characteristics. Strain TP-D1 could degrade 90.4 and 99.7% of TPN after 4-and 7-day incubation in mineral salt broth with 50 mg TPN l -1 and in autoclaved soil with 50 lg TPN g -1 , respectively. Two new metabolites, methyl 2, 5, 6-trichloro-3-cyano-4-methoxy-benzoate (metabolite C) and methyl 3-cyano-2, 4, 5, 6-tetrachlorobenzoate (metabolite D), were detected besides previously reported 4-hydroxy-2, 5, 6-trichloroisophthalonitrile (TPN-OH, metabolite A). This result suggests that the cyano-group in TPN could be converted into amide groups by strain TP-D1, and reveal the biodegradation mechanism of TPN in soil.

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“…Chlorothalonil (CHT, 2,4,5,6-tetrachloro-1,3-benzenedicarbonitrile, Figure 1 ) is a nonsystemic, broad-spectrum fungicide that is currently registered in Massachusetts to control several fruit rots of cranberry. Several studies investigating CHT metabolism in soil ( − ) and sediment () suggest that there are several degradation pathways. Metabolites involving substitution reactions of Cl atoms on the aromatic ring with methyl sulfide, methoxy, and hydroxyl groups or with hydrogen atoms, and conversion of the CN groups to amides, thiazole, and acidic groups, have been identified.…”

Section: Introductionmentioning

confidence: 99%

“…With this research, we will determine if the addition of the spray-tank adjuvant increases application efficacy by prolonging the period that protective residue levels remain on cranberry plants, alters pesticide degradation, or results in higher residues in fruit at harvest. (2,4,5-trichloro-1,3dicyanobenzene, 99.9% pure), VII (4-methylthio-2,5,6-trichloro-1,3dicyanobenzene, 98.8% pure), and IV (4-methoxy-2,5,6-trichloro-1,3dicyanobenzene, 97.6% pure) were generously provided by Dr. Arata Katayama, Nagoya University, Japan. Compounds III (1,3-dicarbamoyl-2,4,5,6-tetrachlorobenzene) and V (1-carbamoyl-3-cyano-4-hydroxy-2,5,6-trichlorobenzene) were synthesized according to the method of Rouchaud et al (13).…”

Section: Introductionmentioning

confidence: 99%

The Persistence and Degradation of Chlorothalonil and Chlorpyrifos in a Cranberry Bog

Putnam

Nelson

Clark

2002

J. Agric. Food Chem.

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The effect of a spray-tank adjuvant on the persistence, distribution, and degradation of two pesticides, chlorothalonil and chlorpyrifos, was studied in a commercial cranberry bog. Pesticides were applied according to label instructions to cranberry plants in paired plot studies. Dislodgeable foliar and whole fruit residues of both pesticides and several degradation products were assessed over a growing season. Residues were also assessed in soil samples collected at fruit harvest. Adjuvant increased both fruit and foliar residues but did not significantly alter the dissipation rate or metabolism of either pesticide. The dissipation of dislodgeable foliar chlorothalonil and chlorpyrifos residues followed first-order kinetics, with estimated half-lives of 12.7 and 3.5 d, respectively. All residue levels on harvested fruit were well below the current U.S. EPA tolerances for fresh cranberries. Chlorothalonil (58%) was the major residue in fruit at harvest (76 d post-chlorothalonil application), with 4-hydroxy-2,5,6-trichloroisophthalonitrile and 1,3-dicarbamoyl-2,4,5,6-tetrachlorobenzene accounting for 26% and 6% of the total residues, respectively. Degradation products accounted for 88% of the total chlorothalonil residues in soil at fruit harvest. The products 1,3-dicarbamoyl-2,4,5,6-tetrachlorobenzene, 1-carbamoyl-3-cyano-4-hydroxy-2,5,6-trichlorobenzene, 2,5,6-trichloro-4-methylthioisophthalonitrile, and 2,4,5-trichloroisophthalonitrile have not been previously identified in cranberry bog environments. Chlorpyrifos was detected in fruit at harvest (62 d post-chlorpyrifos application), but no metabolites were found. Chlorpyrifos-oxon and 3,5,6-trichloro-2-pyridinol, however, were detected in earlier fruit samples and in foliage and soil samples.

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Formation of a Methylthiolated Metabolite from the Fungicide Chlorothalonil by Soil Bacteria

Cited by 12 publications

References 3 publications

Sorption and Degradation of Pesticides in Nursery Recycling Ponds

Sorption and Degradation of Pesticides in Nursery Recycling Ponds

Chlorothalonil degradation by Ochrobactrum lupini strain TP-D1 and identification of its metabolites

The Persistence and Degradation of Chlorothalonil and Chlorpyrifos in a Cranberry Bog

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