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Photodegradation of pyribenzoxim in water

Journal of the Korean Society for Applied Biological Chemistry volume 55, pages 391–396 (2012)Cite this article

Abstract

Photolysis of pyribenzoxim was assessed in various aqueous solutions under sunlight. In direct photolysis, half-lives of pyribenzoxim were 26.9 and 9.2 days for deaerated and nondeaerated distilled water, respectively. Five photoproducts, bispyribac, benzophenone oxime, 2-hydroxy-6-(4,6-dimethoxypyrimidin-2-yloxy)benzoic acid, benzophenone, and 2-hydroxy-6-(4-hydroxy-6-methoxy-pyrimidin-2-yloxy)benzoic acid, were identified after irradiation under a xenon lamp for 4 h. In indirect photolysis, halflives of pyribenzoxim were 6.0, 3.6, 4.8, 2.2, 11.4, and 9.8 days for humic water, paddy water, rose bengal, Fenton’s reagent, furfuryl alcohol, and mixture of furfuryl alcohol and rose bengal. The photolysis rate of pyribenzoxim in Fenton’s reagent aqueous solution was faster than other sensitizers. Furfuryl alcohol, a singlet oxygen quencher, inhibited the photodegradation of pyribenzoxim to some extent.

References

  • Aguer JP and Richard C (1996) Transformation of fenuron induced by photochemical excitation of humic acids. Pestic Sci 46, 151–155.

    Article  CAS  Google Scholar 

  • Buchalska M, Kras G, Oszajca M, Lasocha W, and Macyk W (2010) Singlet oxygen generation in the presence of titanium dioxide materials used as sunscreens in suntan lotions. J Photochem Photobiol A: Chem 213, 158–163.

    Article  CAS  Google Scholar 

  • Burkhard N and Guth JA (1979) Photolysis of organophosphorus insecticides on soil surfaces. Pestic Sci 10, 313–319.

    Article  CAS  Google Scholar 

  • Chang HR, Keum YS, Koo SJ, Moon JK, Kim K, and Kim JH (2011) Metabolism of a new herbicide, [14C]pyribenzoxim in rice. J Agric Food Chem 59, 1918–1923.

    Article  CAS  Google Scholar 

  • Cho BY, Han DS, and Yang JE (1993) Photolysis of a new insecticide KH-502 [O,O-diethyl O-(1-phenyl-3-fluoromethyl-5-pyrazoyl)thiophosphoric acid ester]. Korean J Environ Agric 12, 176–183.

    Google Scholar 

  • Choudhury PP and Dureja P (1997) Studies on photodegradation of chlorimuron-ethyl in soil. Pestic Sci 51, 201–205.

    Article  CAS  Google Scholar 

  • Christopher RL and Irene EK (1996) Does rose bengal triplet generate superoxide anion?. J Am Chem Soc 118, 3297–3298.

    Article  Google Scholar 

  • Christopher RL, Irene EK, and Robert WR (1999) Differential reactivity of upper triplet states produces wavelength-dependent two-photon photosensitization using rose Bengal. J Phys Chem B 103, 3737–3741.

    Article  Google Scholar 

  • Davidson RS (1979) Mechanisms of photo-oxidation reaction. Pestic Sci 10, 158–170.

    Article  CAS  Google Scholar 

  • Faure V and Boule P (1997) Phototransformation of linuron and chloromuron in aqueous solution. Pestic Sci 51, 413–418.

    Article  CAS  Google Scholar 

  • Frank ES and Jurg H (1987) Rate constants for reactions of singlet oxygen with phenols and other compounds in water. Chemosphere 16, 681–694.

    Article  Google Scholar 

  • Franklin V, Mendez VH, and Jenny KR (1998) Photolysis and photosensitized degradation of the diuretic drug acetazolamide. J Photochem Photobiol A 118, 19–23.

    Article  Google Scholar 

  • Fukai Y, Unai T, Ishikawa K, Yusa Y, Wasa N, Tezuku M, and Okada S (1995) Metabolism of ALS inhibitory herbicide bispyribac-sodium [KIH-2023] in rats. J Pestic Sci 20, 479–486.

    Article  CAS  Google Scholar 

  • Gang B, Shizhong T, Zigang F, and Jieke C (1996) Study on the sensitized photolysis of pyrethroid: 1. Kinetic characteristic of photooxidation by singlet oxygen. Chemosphere 32, 1237–1243.

    Article  Google Scholar 

  • Gustavo AP and Damia B (1998) Photosensitized degradation of organic pollutants in water: Processes and analytical applications. Trends Anal Chem 17, 605–612.

    Article  Google Scholar 

  • John MA, Cindy JG, and Sandra KA (1996) Photochemical formation of singlet molecular oxygen (1O2) in illuminated aqueous solutions of paminobenzoic acid (PABA). J Photochem Photobiol B 32, 33–37.

    Article  Google Scholar 

  • Kanner JD and Fennema O (1987) Photooxidation of tryptophan in the presence of riboflavin. J Agric Food Chem 35, 71–76.

    Article  CAS  Google Scholar 

  • Kim KY, Kim J, Liu KH, Lee HS, and Kim JH (2000) In vitro metabolism of pyribenzoxim. Korean Agric Chem Biotechnol 43, 49–53.

    Google Scholar 

  • Koo SJ, Ahn SC, Lim JS, Chae SH, Lee JH, and Cho JH (1997) Biological activity of the new herbicide LGC-40863. Pestic Sci 51, 109–114.

    Article  CAS  Google Scholar 

  • Koo SJ, Kim JS, Kim JS, and Kang SH (2000) Antagonistic interaction of propanil and pyribenzoxim on barnyardgrass control. Pestic Biochem Physiol 67, 46–53.

    Article  CAS  Google Scholar 

  • Laurence L, Charles G, and Jamal O (1999) Photocatalytic degradation of 5-nitro-1,2,4-triazol-3-one NTO in aqueous suspension of TiO2. Comparison with Fenton oxidation. Chemosphere 38, 1561–1570.

    Article  Google Scholar 

  • Liu KH, Moon JK, Kang SH, Koo SJ, Lee HS, and Kim JH (2005) Identification of rat urinal and fecal metabolites of a new herbicide, pyribenzoxim. J Agric Food Chem 53, 6713–6717.

    Article  CAS  Google Scholar 

  • Liu KH, Moon JK, Sung HJ, Kang SH, Koo SJ, Lee HS, and Kim JH (2001) In vivo pharmacokinetics of pyribenzoxim in rats. Pest Manag Sci 57, 1155–1160.

    Article  CAS  Google Scholar 

  • Mazellier P, Jirkovsky J, and Bolte M (1997) Degradation of diuron photoinduced by iron (III) in aqueous solution. Pestic Sci 49, 259–267.

    Article  CAS  Google Scholar 

  • Misra B, Graebing PW, and Chib JS (1997) Photodegradation of chloramben on a soil surface: A laboratory-controlled study. J Agric Food Chem 45, 1464–1467.

    Article  CAS  Google Scholar 

  • Morin B and Cadet J (1994) Benzophenone photosensitization of 2′-deoxyguanosine: Characterization of the 2R and 2S diastereomers of 1-(2-deoxy-β-d-erythro-pentofuranosyl)-2-methoxy-4,5-imidazolidinedione. A model system for the investigation of photosensitized formation of DNA-protein crosslinks. Photochem Photobiol 60, 102–109.

    Article  CAS  Google Scholar 

  • Nowakowska M, Kepczynski M, and Szczubialka K (2001) New polymeric photosensitizers. Pure Appl Chem 73, 491–495.

    Article  CAS  Google Scholar 

  • Partha PC and Prem D (1997) Studies on photodegradation of chlorimuronethyl in soil. Pestic Sci 51, 201–205.

    Article  Google Scholar 

  • Schwack W, Andlauer W, and Armbruster W (1994) Photochemistry of parathion in the plant cuticle environment: Model reactions in the presence of 2-propanol and methyl 12-hydroxystearate. Pestic Sci 40, 279–284.

    Article  CAS  Google Scholar 

  • Schwarzenbach RP, Gschwend PM, and Imboden DM (1993) In Environmental Organic Chemistry, pp. 436–484, John Wiley & Sons Inc, USA.

    Google Scholar 

  • Shin HC, Shim HO, Ahn SC, Cho JH, Chung MK, Han SS, and Roh JK (1998) Pharmacokinetic analysis of a new synthetic acetolactate synthase inhibitors, LGC-40863, in rats. J Pharmacol Exp Ther 285, 795–799.

    CAS  Google Scholar 

  • Tomlin CDS (2006) In The Pesticide Manual, (14th ed), pp. 911–912, BCPC Press, UK.

    Google Scholar 

  • US EPA 712-C-98-060 (1998a) Fate, transport and transformation test guidelines-OPPTS 835.2210, direct photolysis rate in water by sunlight. US Environmental Protection Agency, USA.

    Google Scholar 

  • US EPA 712-C-98-099 (1998b) Fate, transport and transformation test guidelines-OPPTS 835.5270, indirect photolysis screening test. US Environmental Protection Agency, USA.

    Google Scholar 

  • Wang L, Cai W-F, and Li QX (1998) Photolysis of phloxine B in water and aqueous solutions. Arch Environ Contam Toxicol 35, 397–403.

    Article  CAS  Google Scholar 

  • William FS, James DA, Thomas DS, and Robert CS (1980) Conversion of parathion to paraoxon on soil dusts and clay minerals as affected by ozone and UV light. J Agric Food Chem 28, 366–371.

    Article  Google Scholar 

  • Zhang X, Sun DD, Li G, and Wang Y (2008) Investigation of the roles of active oxygen species in photodegradation of azo dye AO7 in TiO2 photocatalysis illuminated by microwave electrodeless lamp. J Photochem Photobiol A: Chem 199, 311–315

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Agricultural Biotechnology, Seoul National University, Seoul, 151-742, Republic of Korea

    Jeong-Han Kim

  2. Environmental Toxicology Research Center, Korea Institute of Toxicology, Daejeon, 305-343, Republic of Korea

    Jong-Su Seo

  3. School of Plant, Life and Environmental Sciences, Hankyong National University, Ansung, 456-749, Republic of Korea

    Joon-Kwan Moon

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  1. Jong-Su Seo
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Correspondence to Jeong-Han Kim.

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Seo, JS., Moon, JK. & Kim, JH. Photodegradation of pyribenzoxim in water. J Korean Soc Appl Biol Chem 55, 391–396 (2012). https://doi.org/10.1007/s13765-012-2042-4

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