Abstract

A series of 30 neonicotinoid insecticides, bearing nitroconjugated double bond and five-membered heterocycles and nitromethylene compounds containing a tetrahydropyridine ring with exo-ring ether modifications, active against the cowpea aphids (Aphis craccivora), was analyzed using multiple linear regression (MLR) method. The semiempirical quantum chemical PM7 approach was employed for structure optimization. Structural descriptors were calculated for the minimum energy conformers and were related to the insecticidal activity (expressed as pLC50 values) through genetic algorithm, using the multiple linear regression (MLR) approach. Several parameters were applied to check the internal and external model validation. The final MLR models demonstrated good statistical results and predictive power. The presence of more than 6-membered rings, a large number of rings containing secondary C(sp3) atoms, and/or higher values of strongest basic pKa in the core structure of neonicotinoids are considered to decrease the insecticide activity.

Highlights

  • Neonicotinoids are considered to be one of the most important and relevant classes of insecticides used nowadays [1, 2].They are active on the insect postsynaptic nicotinic acetylcholine receptors and still of current interest, despite their resistance and bee toxicity [3]

  • The semiempirical quantum chemical PM7 approach was employed for structure optimization

  • Structural descriptors were calculated for the minimum energy conformers and were related to the insecticidal activity through genetic algorithm, using the multiple linear regression (MLR) approach

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Summary

Introduction

Neonicotinoids are considered to be one of the most important and relevant classes of insecticides used nowadays [1, 2]. They are active on the insect postsynaptic nicotinic acetylcholine receptors (nAChRs) and still of current interest, despite their resistance and bee toxicity [3]. Several studies of computational chemistry and electrophysiology tried to model the neonicotinoid-receptor interactions. Electrostatic interactions and possibly hydrogen bond formation were found to be important for the insecticidal activity [4]. Good correlation of compound structural features with the insecticide activity was noticed, but models with modest predictive power. It was found that high values of squared octanol-water partition coefficients and of tautomers were favorable for the insecticidal activity

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