PEMODELAN DAN ANALISIS QSAR SENYAWA TURUNAN AMINOSULFENIL METILKARBAMAT SEBAGAI INSEKTISIDA MENGGUNAKAN METODE SEMIEMPIRIK AUSTIN MODEL 1; MODELING AND QSAR ANALYSIS OF AMINOSULFENYL METHYLCARBAMATE DERIVATIVES AS INSECTICIDE USING SEMIEMPIRIC AUSTIN MODEL 1 METHOD

GERRY NUGRAHA, Dwi Siswanta

2011 | Disertasi | PROGRAM STUDI S2 ILMU KIMIA

Design of insecticide compounds of aminosulfenyl methylcarbamate derivative based on QSAR (Quantitative Structure Activity Relationship) model have been investigated. Acivities of aminosulfenyl methylcarbamate derivatives obtained from the literature. Calculation descriptors and modeling structure of aminosulfenyl methylcarbamate derivative compounds have done by Austin Model 1 method. QSAR analysis has performed by linier multiple regression method to get the best QSAR model for predicting activity of insects and mammals, the best model is: Insects Log LD50 = 28,655 + 409,682 qC2 + 111,990 qO4 – 68,932 qC5 + 79,603 qC9 + 36,628 qO12 + 14,228 qO15 + 18,116 qC16 – 15,488 qS17 + 5,022 qN18 – 0,105 dipole – 0,044 Log P + 0,054 Polarizability (n= 43, R= 0,928, SE= 0,176, Fcal/Ftab= 6,865, PRESS= 0,242) Mammals Log LD50 = 6,984 + 28,671 qO15 - 6,986 qN18 - 0,091 dipole -0,180 Log P + 0,053 Polarizability (n = 13, R = 0,977, SE = 0,042, Fcal/Ftab= 7,326, PRESS = 0,006) Based on the model above, a new compound have designed for new insecticide aminosulfenyl methylcarbamate derivative with high activity for insect but low for mammals. Double substituted compounds with curcumin and (CH2)2COOC2H5 namely ethyl 3-((((((2,2-dimethyl-2,3-dihydrobenzofuran-7-yl) oxy)carbonyl) (methyl)amino)thio) ((4-((1E,6E)-7-(4-hydroxy-3-methoxyphenyl)- 3,5-dioxohepta-1,6-dien-1-yl)- 2-methoxyphenoxy)methyl)amino)propanoate have highly activity for insects (LD50=0.71 ?g/g) and low activity for mammals (LD50=60.316,23 g/kg). This compound is recommended to be synthesized in the laboratory as a new insecticide.

Kata Kunci : Insektisida metilkarbamat, QSAR, semiempirik, AM1