Analysis of the chemical reactivity of indaziflam herbicide and its metabolites through global and local reactivity descriptors

Abstract

In the present work, the chemical reactivity of indaziflam N-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1 yl]-6-[(1R)-1-16 fluoroethyl]-1,3,5-triazine-2,4-diamine so called indaziflam (IND) and its metabolites: triazine indanone (ITI), indaziflam carboxylic acid (ICA) and fluoroethyldiaminotriazine (FDAT) was analyzed. The calculations were performed at the X/6 311++G(2d,2p) (where X=B3LYP, M06, M06L and wB97XD) level of theory, in the aqueous phase. The results indicate that ITI is the more reactive followed by ICA, IND and FDAT. The distribution of the active sites was determined evaluating the Fukui function employing the frozen core and finite difference approximations. For electrophilic attacks, IND shows the more reactive zone on the benzene ring, ITI and ICA on the nitrogen atom in the central section and FDAT on its nitrogen atoms. The more nucleophilic sites for IND are observed on the carbon atoms of triazine, on the carbonyl group for ITI, on the carboxylic group for ICA, and on the nitrogen atoms of triazine for FDAT. For free radical attacks case, the more reactive sites for IND are on the benzene and triazine rings, on the carbonyl group, nitrogen of the central section, and nitrogen atoms of triazine, for ITI, carboxylic group for ICA, and on the nitrogen atoms of triazine ring for FDAT.

Keywords

• indaziflam
• Fukui function
• dual descriptor, DFT