Photodecomposition of a Herbicide, Butachlor

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  • CHEN Yuh-Lin
    Department of Agricultural Chemistry, National Taiwan University
  • CHEN Chien-Chih
    Department of Agricultural Chemistry, National Taiwan University

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  • 除草剤ブタクロールの光分解

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Abstract

Photodecomposition of the herbicide, butachlor [2-chloro-2′, 6′-diethyl-N-(butoxymethyl)acetanilide, Machete®], as thin film on glass under UV light was very fast. The half life was found to be about 1.5hr under the experimental condition. The decomposition reaction followed first order kinetics. At least 7 decomposition products were observed by Tlc and Glc analyses. The main degradation pathways involved debutoxymethylation, dechlorination, hydroxylation, O-dealkylation, dehydrogenation, cyclization and polymerization. Among the photodecomposed products, 2-chloro-2′, 6′-diethylacetanilide was identified by means of Tlc, Glc, IR, mass and NMR analyses with comparison to authentic sample. Four components with molecular wt of 218, 219 (C13H17NO2), 223 (C12H14NOCl) and 293 (C17H27NO3) were determined by GC-MS. Three of them were assigned to be 2-hydroxy-2′, 6′-diethyl-N-(butoxymethyl)acetanilide (mol wt 293), 1-chloroacetyl-2, 3-dihydro-7-ethylindole (mol wt 223) and N-2′, 6′-diethylphenyl-2, 5-dihydrooxazol-4-one (mol wt 219) respectively from the evidence of IR and mass spectra.

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