Inhibition of acetylcholinesterase activity by impurities in technical grades and purified flupyrazofos

Flupyrazofos 원제 및 정제품의 불순물 조성과 Acetylcholinesterase에 대한 저해 비교

  • You, Kyoung-Youl (Research Institute SUNGBO Chemicals Co., Ltd.) ;
  • Cho, Boo-Yeon (Research Institute SUNGBO Chemicals Co., Ltd.) ;
  • Park, Dong-Sik (Division of Biological Environment, College of Agricultural and Life Sciences, Kangwon National University) ;
  • Hur, Jang-Hyun (Division of Biological Environment, College of Agricultural and Life Sciences, Kangwon National University)
  • 유경렬 ((주)성보화학 중앙연구소) ;
  • 조부연 ((주)성보화학 중앙연구소) ;
  • 박동식 (강원대학교 농업생명과학대학 생물환경학부) ;
  • 허장현 (강원대학교 농업생명과학대학 생물환경학부)
  • Published : 2005.03.31


Flupyrazofos (O,O-diethyl O-1-phenyl-3-trifluoromethylpyrazo-5-yl phosphorothioate) is an organophosphorus insecticide with a pyrazole moiety which is newly developed and commercialized by SUNGBO chemical company and Korean Research Institute of Chemical Technology for effectively control against diamond back moth. This study was conducted to determine the composition and quantity of impurities in technical 1 (94.5%), technical 2 (97.6%) and purified (99.2%) flupyrazofos using GLC/MSD. Bimolecular inhibition rate constant($k_i$) with acethylcholinesterase (in vitro) and $I_{50}$ with mouse brain acetylcholinesterase (in vivo) were measured for comparing inhibitory patterns of two technicals and purified flupyrazofos. Impurities of flupyrazofos were identified as O,O,O-triethylthio-phosphoric acid (TEA), 1-phenyl-3-trifluoromethyl-5-ethoxy pyrazole(PTMEP), O,O-diethyl O-1-phenyl-3-trifluoromethylpyrazo-5-yl phosphoric acid ester(flupyrazofos oxen), O,S-diethyl O-1-phenyl-3-trifluoromethylpyrazo-5-yl phosphorothionate (S-ethyl flupyrazofos). In in vitro, technical 1 showed the fastest inhibition on AChE activity among them. And technical 1 and 2 showed 40% higher in vivo inhibition against mouse brian AChE than purified flupyrazofos did. These results could be caused by the impurities such as flupyrazofos oxen and S-methyl flupyrazofos contained in technical grades of flupyrazofos.


  1. Elliman, G. L., K. D. Coutney, V. Andress and R. M. Featherstone (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 7:88-91
  2. Kim, S. K., K. G. Lee, H. W. Kim, S. E. Yoo, K. J. Hwang and Y. D. Gong (2004) Insecticidal activity of flupyrazofos KH502 against Plutella xylostella: a CoMFA study. Korean. J. Pestic. Sci. 8(3):162-167
  3. 김영배, 이성규, 김용화, 노정구 (1988) Diazinon과 carbofuran의 송사리(Oryzias latipes)와 미꾸리(Misgurnus anguillicaudatus)에 대한 선택적 독성과 acetylcholinesterase 저해. 한국환경농학회지 7(2):117-123
  4. Chung, M. K., J. C. Kim and S. S. Han (2002) Developmental toxicity of flupyrazofos, a new organophosphorus insecticide, in rats. Food Chem. Toxicol. 40:723-729
  5. 김정호, 홍종욱 (1987) 유기인계 살충제 Phorate가 acetylcholinesterase 활성에 미치는 영향. 한국환경농학회지 6(2):77-83
  6. Aldridge, W. N. (1950) Some properties of specific cholinesterase with particular reference to mechanism (E605) and analogues. J. Biochem. 46:451-456
  7. Holligworth, R. H. (1989) Investigations into the chemistry, toxicology, metabolism and possible mode of action O-ethyl S-methylethylphosphonothioate, Ph.D. Dissertation, University of California, Riverside. 46-52
  8. 송시환, 김형진, 신천철, 임광현, 하창수, 한상섭 (1998) KH-502의 랫트 및 마우스를 이용한 급성독성시험. 한국독성학회지 14(2):227-235
  9. Vale, J. A. (1998) Toxicokinetic and toxicodynamic aspects of organophosphorus (OP) insecticide poisoning. Toxicol. Lett. 102:649-652
  10. 조부연, 한대성 (1992) 신규 살충제인 O,O-diethyl O-(1-phenyl-3-trifluoromethyl-5-pyrazoyl) thiophosphoric acid ester (KH-5-2)의 열에 의한 분해성. 한국환경농학회지 11(3):225-234