Transformation of the fungicide chlorothalonil by Fenton reagent.
A modified Fenton reagent (Fe(3+)/H(2)O(2)) transformed the fungicide chlorothalonil within 60 min in aqueous solution at unadjusted pH. Transformation varied with ferric salt. Transformation was greatest with ferric nitrate and least when ferric sulfate was used. UV irradiation enhanced the transformation of chlorothalonil. The transformation of chlorothalonil was enhanced, which increased with ferric ion or hydrogen peroxide concentration. Maximum transformation was achieved at 2 mM ferric ion and 100 mM hydrogen peroxide. Additionally, chlorothalonil was more dechlorinated in the UV irradiation condition. The proposed reaction pathway includes reduction of chlorothalonil to trichloroisophthalonitrile, dichloroisophthalonitrile, and monochloroisophthalonitrile; oxidation of trichloroisophthalonitrile to trichloro-3-cyanobenzoic acid and 3-carbamyltrichlorobenzoic acid; and oxidation of hydroxychlorothalonil to trichloro-3-cyanohydroxybenzoic acid and trichlorocyanophenol.
Park
Jong-Woo
JW
Department of Agricultural Chemistry, Kyungpook National University, 1370, Sankyuk dong, Buk-gu, Daegu 702-701, Korea.
Lee
Sung-Eun
SE
Rhee
In-Koo
IK
Kim
Jang-Eok
JE
D002713:Chlorine / Q000737:chemistry; D005290:Ferric Compounds / Q000008:administration & dosage / Q000737:chemistry; D005659:Fungicides, Industrial / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D006861:Hydrogen Peroxide / Q000008:administration & dosage / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007501:Iron / Q000737:chemistry*; D007700:Kinetics; D009566:Nitrates / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry*; D012996:Solutions; D013997:Time Factors; D014466:Ultraviolet Rays; D014867:Water
C045076:Fenton's reagent; D005290:Ferric Compounds; D005659:Fungicides, Industrial; D009566:Nitrates; D009570:Nitriles; D012996:Solutions; D014867:Water; C024823:ferric sulfate; D002713:Chlorine; D006861:Hydrogen Peroxide; D007501:Iron; C005806:tetrachloroisophthalonitrile; C025302:ferric nitrate