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.
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.
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...
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 investigated, using the comparative molecular field analysis (CoMPA) method, The structure-activity relationship of various thiophosphorylpyrazole derivatives and structure requirement for insecticidal activity. We found, the key substructures in pyrazole derivatives, the trifluoro-methyl group and the thiophosphoryl group. Both play an important role in insecticidal activity with the binding site. The three dimensional Quantitative Structure Activity Relationship (QSAR) analysis could provide useful information for the structural requirements of pyrazole insecticide as an insecticidal and the design of a new insecticide.
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 investigated, using the comparative molecular field analysis (CoMPA) method, The structure-activity relationship of various thiophosphorylpyrazole derivatives and structure requirement for insecticidal activity. We found, the key substructures in pyrazole derivatives, the trifluoro-methyl group and the thiophosphoryl group. Both play an important role in insecticidal activity with the binding site. The three dimensional Quantitative Structure Activity Relationship (QSAR) analysis could provide useful information for the structural requirements of pyrazole insecticide as an insecticidal and the design of a new insecticide.
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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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SYBYL Molecular Modeling System, Version 6.7; Tripos, Inc., St. Louis, MO 63144
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