• Title/Summary/Keyword: Hydrolysis degree

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On the Utilization of Inactive BHC isomers -Synthesis of 3-(2,4,5-trichlorophenyl)-1-methyl urea as a herbicide- (BHC 이성질체(異性質體)의 활용(活用)에 관(關)한 연구(硏究) -제초제(除草劑)로서 3-(2,4,5-trichlorophenyl)-1- methyl urea의 합성(合成)-)

  • Lee, Kyu-Seung;Park, Chang-Kyu
    • Applied Biological Chemistry
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    • v.22 no.2
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    • pp.109-122
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    • 1979
  • Present study was carried out to reduce residual toxicity of BHC insecticides inherent in the organochlorine pesticides. For This end, r-isomer, the most potent insecticidal component among the BHC stereoisomers, was isolated and thus fortified by means of solvent precipitation. In parallel, 3-(2,4,5-trichlorophenyl)-1-methyl urea was prepared in good yield from technical BHC via 1,2,4-trichlorobenzene, 1,2,4,-trichloronitrobenzene, and 2,4,5-trichloroaniline. In addition, certain merit of the compound which make it possible to use as a herbicide is discussed. The results are summarized as follows; 1. Recrystallizing technical BHC from methanol-water binary solvent system, r-isomer was enriched to 49.7% at 95% recovery of r-isomer. 2. By partitioning technical BHC in 85% of methanolic solution into chloroform, r-isomer was fortified to 89.6% at 90.5% recovery of r-isomer. 3. Yield of 1,2,4-trichlorobenzene from technical BHC was greatly dependent upon concentration of alkalies and to less degree on the alkalies. 4. Surfactants, in particular cationic a quartenary ammonium salt, increased yield of 1,2,4-trichlorobenzene from technical BHC by alkaline hydrolysis. 5. Conversion of 1,2,4-trichlorobenzene to 2,4,5-trichloronitrobenzene was effected almost quantitatively utilizing $HNO_3-H_2SO_4$ nitrating agent at low temperature. 6. Yield of 91.4% was observed for the synthesis of 2,4,5-trichloroaniline by reducing 2,4,5-trichloronitrobenzene in the presence of iron turning and hydrochloric acid. 7. Overall yield based on BHC of 3-(2,4,5-trichlorophenyl)-1- methyl urea was 60.8%. 8. Inhibition effects, both germination and growth, 3-(2,4,5-trichlorophenyl)-1-methyl urea on several crops were found comparable to or more potent than those of $linuron{\circledR}\;and\;diuron{\circledR}$. In addition, it was also noted that susceptibility to the prepared compound depended upon the crops as well as specific part (shoots, roots) of the plant exposed to the chemicals.

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