Photochemical reaction of 2,4,5,6-tetrachloroisophthalonitrile

Binkley, Roger W.; Kirstner, Gretchen L.; Opaskar, Vincent C.; Olynyk, Paul

doi:10.1016/0045-6535(77)90129-1

Cited by 13 publications

(4 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…During the microbial degradation of chlorothalonil, dehalogenation also occurs at the fourth site (Wang et al, 2010). The 4-chlorine atom of chlorothalonil is presumed to be the most susceptible chlorine atom to being replaced (Binkley et al, 1977). It appears that the 4-chlorine atom of o-tetrachlorophthalonitrile is also the most susceptible chlorine atom to being substituted.…”

Section: Effect Of Environmental Factors On the Biodegradation Of O-tmentioning

confidence: 99%

Hydrolytic dehalogenation of the chlorothalonil isomer o-tetrachlorophthalonitrile by Pseudochrobactrum sp. BSQ-1

Liu

Gou

et al. 2016

International Biodeterioration & Biodegradation

View full text Add to dashboard Cite

Microbial dehalogenation plays key roles in the biodegradation and detoxification of halogenated aromatics. Although the hydrolytic dehalogenation of halogenated aliphatic hydrocarbons and carboxylic acids has been extensively studied, there are few reports on the hydrolytic dehalogenation of halogenated aromatics. In this study, the aerobic strain BSQ-1, isolated from soils contaminated with halogenated aromatics in Jiangsu, China, was able to completely degrade 0.12 mM o-tetrachlorophthalonitrile in 84 hours in the presence of 2 mM sodium acetate trihydrate and released one equivalent of chlorine ions. MS-MS and NMR analysis revealed that o-tetrachlorophthalonitrile was dehalogenated to 4-hydroxyl-o-trichlorophthalonitrile. The dehalogenation of o-tetrachlorophthalonitrile could occur under both aerobic and anaerobic conditions, showing that the observed dehalogenation was a hydrolytic process. The optimal temperature and pH for o-tetrachlorophthalonitrile dehalogenation by strain BSQ-1 were 30°C and 8, respectively. It was found that 0.2 mM Zn 2+ , Mg 2+ or Co 2+ enhanced dehalogenation activity, whereas 0.2 mM Fe 3+ , Ni 2+ , Cu 2+ , Ca 2+ , or Pb 2+ inhibited dehalogenation activity. Strain BSQ-1 was able to dehalogenate not only

show abstract

Section: Effect Of Environmental Factors On the Biodegradation Of O-tmentioning

confidence: 99%

Hydrolytic dehalogenation of the chlorothalonil isomer o-tetrachlorophthalonitrile by Pseudochrobactrum sp. BSQ-1

Liu

Gou

et al. 2016

International Biodeterioration & Biodegradation

View full text Add to dashboard Cite

show abstract

“…Therefore, the compound ( II) appears to be a product of I formed by the replacement of one chlorine atom with a lactonic carbonyl functionality. Earlier studies (Binkley et al 1977) revealed that 4-chlorine atom is most susceptible to such replacement. The 1 H NMR spectrum of II revealed the presence of three methyl protons at δ 1.78(d) and one methine (CH) proton at δ 5.62(q).…”

Section: Compoundsmentioning

confidence: 99%

“…The 1 H NMR spectrum exhibited a sharp singlet for two protons at 6 5.32. All the above data could only be fitted with the structure of 4,5,7 -trichloro -6-cyano -3, 3 -dihydro -lisobenzotiranone previously reported by Binkley et al (1977).…”

Section: Compoundsmentioning

confidence: 99%

“…Several studies on the photochemical transformation of I in different organic solvents, viz., benzene (Khan and Akhtar 1983 and references cited therein), dichloromethane (Dureja and Walia 1993), ethanol (Giumanini et al 1989), methanol (Binkley et al 1977) have been reported, but no attempt has been made to evaluate the toxicity of the transformed products. The present study has, therefore, been intended to re-investigate the transformation of I in alcohols (ethanol and methanol) under ultra violet irradiation for evaluation of the relative toxicity of the transformed products formed under the process.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Photochemical Transformation of the Fungicide Chlorothalonil by Ultra Violet Radiation

Samanta¹,

Kole²,

Ganguly

et al. 1997

Bulletin of Environmental Contamination and Toxicology

View full text Add to dashboard Cite

Among the chlorinated aromatics, nitriles represent an increasingly important group of pesticides of which chlorothalonil (2,4,5,6-tetrachloroisophthalonitrile, I ) is a broad spectrum fungicide used against many plant pathogens affecting a large number of agricultural crops. Several studies on the photochemical transformation of I in different organic solvents, viz., benzene (Khan and Akhtar 1983 and references cited therein), dichloromethane (Dureja and Walia 1993), ethanol (Giumanini et al. 1989), methanol (Binkley et al. 1977 have been reported, but no attempt has been made to evaluate the toxicity of the transformed products. The present study has, therefore, been intended to re-investigate the transformation of I in alcohols (ethanol and methanol) under ultra violet irradiation for evaluation of the relative toxicity of the transformed products formed under the process. MATERIALS AND METHODSChlorothalonil was purified from commercial 'Kaboch' formulation (75% wettable powder) by dissolving it in chloroform and filtered. The concentrated filtrate was further purified by coloumn chromatography over silica gel and crystallised from petroleum ether-chloroform. Its purity (98.0%) was determined by TLC and HPLC (mp 250-251°C) and its authenticity was confirmed by IR,MS and NMR spectral data. Solvents used in the study were HPLC grade ( E Merck , India ) and all inorganic reagents were laboratory grade. Melting points were determined by an electrically heated mp apparatus and are uncorrected. Infrared spectra (IR) were determined on potassium bromide discs using a Perkin Elmer model 1310 spectrophotometer. 1 H and 13 C nuclear magnetic resonance (NMR) spectra were recorded at 100 MHz using a JEOL model JNM-FX 100 engine using tetramethylsilane (TMS) as the internal standard. Samples were dissolved in deuterochloroform. The mass spectra (MS) were obtained by direct sample probe on a JEOL Model JMS-DX 300 instrument at 70 ev.High pressure liquid chromatograph (HPLC) of Hewlett Packard Model 1050 equipped with a UV variable detector Model 1050 coupled with a HP 3392A integrator was used for the analysis of chlorothalonil and its metabolites. The reverse phase column (length 25 cm; id 4.6 cm; od 0.635 cm) was packed with Hypersil

show abstract

Identification of the photochemical decomposition product of chlorothalonil by ¹³C n.m.r. spectroscopy

Loeffler¹

1978

Pestic. Sci.

View full text Add to dashboard Cite

show abstract

Photochemical reaction of 2,4,5,6-tetrachloroisophthalonitrile

Cited by 13 publications

References 13 publications

Hydrolytic dehalogenation of the chlorothalonil isomer o-tetrachlorophthalonitrile by Pseudochrobactrum sp. BSQ-1

Hydrolytic dehalogenation of the chlorothalonil isomer o-tetrachlorophthalonitrile by Pseudochrobactrum sp. BSQ-1

Photochemical Transformation of the Fungicide Chlorothalonil by Ultra Violet Radiation

Identification of the photochemical decomposition product of chlorothalonil by ¹³C n.m.r. spectroscopy

Contact Info

Product

Resources

About

Photochemical reaction of 2,4,5,6-tetrachloroisophthalonitrile

Cited by 13 publications

References 13 publications

Hydrolytic dehalogenation of the chlorothalonil isomer o-tetrachlorophthalonitrile by Pseudochrobactrum sp. BSQ-1

Hydrolytic dehalogenation of the chlorothalonil isomer o-tetrachlorophthalonitrile by Pseudochrobactrum sp. BSQ-1

Photochemical Transformation of the Fungicide Chlorothalonil by Ultra Violet Radiation

Identification of the photochemical decomposition product of chlorothalonil by 13C n.m.r. spectroscopy

Contact Info

Product

Resources

About

Identification of the photochemical decomposition product of chlorothalonil by ¹³C n.m.r. spectroscopy