Effect of pH on the hydrolysis of chlorothalonil

Szalkowski, Mary B.; Stallard, Don E.

doi:10.1021/jf60209a014

Cited by 55 publications

(21 citation statements)

References 2 publications

(2 reference statements)

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“…It indicated that metabolites C and D derived from TPN degradation. We assume that metabolites C and D come from CCHT (Rouchaud and Roucourt 1988) and 3-cyano-2,4,5,6-tetrachlorobenzamide (CTB) (Szalkowski and Stallard 1977), respectively. CTB has been detected as a chemical hydrolysis product of TPN at pH 9.0 (Szalkowski and Stallard 1977); however, it is a former product of DTTC.…”

Section: Discussionmentioning

confidence: 99%

“…We assume that metabolites C and D come from CCHT (Rouchaud and Roucourt 1988) and 3-cyano-2,4,5,6-tetrachlorobenzamide (CTB) (Szalkowski and Stallard 1977), respectively. CTB has been detected as a chemical hydrolysis product of TPN at pH 9.0 (Szalkowski and Stallard 1977); however, it is a former product of DTTC. DTTC and CCHT have been recovered from soil under field conditions, and are thought to be the biodegradation products under mild conditions (Rouchaud and Roucourt 1988).…”

Section: Discussionmentioning

confidence: 99%

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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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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

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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show abstract

“…A calibration curve obtained for chlorothalonil using a series of working standard solutions over a concentration range from 0.3 to 300 ng mL -1 showed excellent linearity (r 2 > 0.99). Although moderate hydrolysis of chlorothalonil under a basic condition was previously reported, 21 obvious degradation was not observed during the LC/MS operation. The instrumental detection limit (IDL) was determined by multiplying the standard deviation of the quantified values of standard solutions for seven replicate measurements.…”

Section: Appi Characteristicsmentioning

confidence: 74%

Analysis of Chlorothalonil by Liquid Chromatography/Mass Spectrometry Using Negative-ion Atmospheric Pressure Photoionization

et al. 2009

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“…Chlorothalonil is stable to hydrolysis at pH 5 and 7 (Szalkowski and Stallard 1977;US EPA 1999). However, under basic conditions (pH 9), the compound degrades to form two products: 3-cyano-2,4,5,6-tetrachlorobenzamide and 4-hydroxyl-2,5,6-trichloroisophthalonitrile (Szalkowski and Stallard 1977).…”

Section: Hydrolysismentioning

confidence: 99%

“…However, under basic conditions (pH 9), the compound degrades to form two products: 3-cyano-2,4,5,6-tetrachlorobenzamide and 4-hydroxyl-2,5,6-trichloroisophthalonitrile (Szalkowski and Stallard 1977). Kwon and Armbrust (2006) proposed that the pathway for chlorothalonil degradation in aquatic systems would proceed by reductive dechlorination, oxidative dechlorination/hydrolysis and base hydrolysis (Fig.…”

Section: Hydrolysismentioning

confidence: 99%