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배추좀나방에 대한 flupyrazofos KH502의 살충활성 CoMFA

Insecticidal activity of flupyrazofos KH502 against Plutella xylostella: a CoMFA study

농약과학회지 = The Korean journal of pesticide science, v.8 no.3, 2004년, pp.162 - 167  

김수경 (한국화학연구원 생명의약연구부) ,  이관구 (한국화학연구원 생명의약연구부) ,  김혜원 (한국화학연구원 생명의약연구부) ,  유성은 (한국화학연구원 생명의약연구부) ,  황기준 (전북대학교 화학과) ,  공영대 (한국화학연구원 생명의약연구부)

초록
AI-Helper 아이콘AI-Helper

십자화과 식물을 가해하는 세계적으로 중요한 해충의 하나인 배추좀나방(diamondback moth, Plutella xylostella)을 방제를 하기위하여 개발된 새로운 형태의 thiophosphoryl pyrazole계 살충제 KH502 유도체들의 구조와 살충활성을 CoMFA 방법으로 조사한 결과 효소의 결합부위에서 가장 중요한 역할을 하는 작용기는 trifluoro-methyl group과 thiophosphoryl group으로 밝혀졌다. 이와 같은 3D-QSAR 분석결과는 새로운 배추좀나방 방제용 살충제를 설계하는데 유용한 정보로 이용할 수 있을 것이다.

Abstract AI-Helper 아이콘AI-Helper

In recent years, the diamondback moth (DBM), Plutella xylostella has become one of the most important pests for cruciferous plants in the world. A new type of the thiophosphoryl pyrazole insecticide, called KH502. Its outstanding insecticidal activity could be effective alternative against DBM. We i...

주제어

AI 본문요약
AI-Helper 아이콘 AI-Helper

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제안 방법

  • The grid points were regularly spaced per 2 A to form a grid box (18X20X22 A), following the automatic procedure in CoMFA program. After constructing the CoMFA lattice, the interaction energy of steric and electrostatic fields was calculated for each molecule at every the grid point surrounding the aligned molecules in 3D-space. To correlate these fieldenergy terms with their DBM insecticidal activity, a partial least square (PLS) analysis was used with cross validation to measure the predictive power of the model and to get the optimum number of components for the next step.
  • In order to test the predictability of the CoMFA model S, we calculated, by usin흥 model B through a regression equation from CoMFA (Table 3), the insecticidal activities of three compound whose actual activities were known in the te아 sets. The calculation results showed that the calculated log(LC5o) was well predicted by the model B.
  • The steric and electrostatic fields were scaled according to CoMFA standard deviation in order to give them the same potential weights on the resulting QSAR. The constructed 3D-QSAR PLS model was then used to predict the insecticidal activity of new compounds, replacing X group with 221 new substituents, as suggested by the CoMFA module (Table 4).
  • To correlate these fieldenergy terms with their DBM insecticidal activity, a partial least square (PLS) analysis was used with cross validation to measure the predictive power of the model and to get the optimum number of components for the next step. The final PLS analysis was perfonned by no-cross validation with an optimum number of components reported from the cross validation result. The steric and electrostatic fields were scaled according to CoMFA standard deviation in order to give them the same potential weights on the resulting QSAR.
  • The final PLS analysis was perfonned by no-cross validation with an optimum number of components reported from the cross validation result. The steric and electrostatic fields were scaled according to CoMFA standard deviation in order to give them the same potential weights on the resulting QSAR. The constructed 3D-QSAR PLS model was then used to predict the insecticidal activity of new compounds, replacing X group with 221 new substituents, as suggested by the CoMFA module (Table 4).
  • After constructing the CoMFA lattice, the interaction energy of steric and electrostatic fields was calculated for each molecule at every the grid point surrounding the aligned molecules in 3D-space. To correlate these fieldenergy terms with their DBM insecticidal activity, a partial least square (PLS) analysis was used with cross validation to measure the predictive power of the model and to get the optimum number of components for the next step. The final PLS analysis was perfonned by no-cross validation with an optimum number of components reported from the cross validation result.

대상 데이터

  • 7)program (Gasteiger and Marsili, 1980; Streitwieser, 1961). A set of 31 pyrazole derivatives with various R1, R2 and R3 were grouped as models, A and B were used for the 3D-QSAR study (Table 1). In our first work, we studied the derivatives of model A where only R1 group was changed, without variation in the R2 and R3 groups.

이론/모형

  • 05 kcal/mol/A. Partial atomic charges required for the calculation of the electrostatic interaction energies were calculated by the Gasteiger-Huckel method (SYBYL Molecular Modeling System). A grid search was performed chmging ratable torsional angles by 60° increments from 0 to 360°.
  • Our study aimed to understand the physicochemical effects of the substituents, R1 on the pyrazole ring, on the insecticidal activity measured with DBM. The analysis has been made quantitatively with physicochemical substituents and/or molecular parameters and regression analysis (3D-QSAR).
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참고문헌 (15)

  1. Chu, Y.I. (1992) The migration of diamondback moth. In Talekar, N.S. and Griggs, T.D. (eds) Diamondback moth. pp. 77-81, Management Proceedings of First International Workshop. Asian Vegetable Research and Development Center, Shanhua, Tainan,Taiwan(ROC) 

  2. K. Kim, J.H. Kim, and Y.H. Kim (1997) Study on physiochemical properties of pesticides II-water solubility, hydrolysis, vapor pressure and octanol/water partition coefficient of flupyrazofos Agr. Chem. Biotechnol. 40 (I) : 76-79 

  3. Sung-Bo Chemical Co. Report, Korea (1996) 

  4. K.J. Hwang, Y.-D. Gong, and G.H. Kim (1988) Korea Patent No. 36152 

  5. K.J. Hwang, Y.-D. Gong, and G.H. Kim (1989) US Patent No. 4822779 

  6. K.J. Hwang, Y.-D. Gong, and G.H. Kim (1989) Preparation and testing of insecticidal phosphoric and thiophosphoric acid ester of 5-hydroxypyrazoles, compositions and use. Chemical Abstracts. 111:696 

  7. B.Y. Cho, and D.S. Han (1992) Thermal decomposition of a new insecticide, KH502 [o,o-diethyl-o-(1-phenyl-3-trifluoromethyl- 5-pyrazoyl)thiophosphoric acid ester]. Korean J. Environ. Agric. 11:225-243 

  8. B.Y. Cho, and D.S. Han and J.E. Yang, (1993) Photolysis of a new insecticide KH502 [o,o-diethyl o-(1-phenyl-3-trifluoromethyl-5-pyrazoyl)thiophosphoric acid ester]. Korean J. Environ. Agric. 12:176-183 

  9. H.S. Lee, S. Jeong, K. Kim, J.H. Kim, S.K. Lee, B.H. Kang, and J.K. Roh (1997) In vitro metabolism of the new insecticide flupyrazofos by rat liver microsomes. Xenobiotica. 27:423-429 

  10. J.H. Kim, K.G. Kang, C.K. Park, K. Kim, B.H. Kang, S.K. Lee and J.K. Roh (1998) Aerobic soil metabolism of flupyrazofos. Pestic. Sci., 54:237-243 

  11. C.K. Jeong, H.Y. Lee, S.B. Kim, S.J. Choi, J.H. Kim, K. Kim, S.S. Han, and H.S. Lee (2001) Metabolism of flupyrazofos in the isolated rat liver. Pest Manag. Sci. 57:427-431 

  12. R.D. Cramer, D.E. Patterson, and J.D. Bunce (1988) Comparative molecular field analysis (CoMFA). I. Effect of shape on binding of steroids to carrier proteins, J. Am. Chem. Soc. 110:5959-5967 

  13. J. Gasteiger and M. Marsili (1980) Iterative partial equalization of orbital electronegativity a rapid access to atomic charge, Tetrahedron 36:3219-3228 

  14. Streitwieser A. (1961) Molecularorbital theory for organic chemists, New York: Wiley 

  15. SYBYL Molecular Modeling System, Version 6.7; Tripos, Inc., St. Louis, MO 63144 

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