Insecticidal and neuroblocking potencies of variants of the thiazolidine moiety of thiacloprid and quantitative relationship study for the key neonicotinoid pharmacophore

Kagabu, Shinzo; Nishimura, Keiichiro; Naruse, Yuji; Ohno, Ikuya

doi:10.1584/jpestics.r07-25

Cited by 18 publications

(19 citation statements)

References 38 publications

(83 reference statements)

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“…It has high stability and good water solubility (184 mg L -1 at 20 °C), thus it can accumulate in the environment and have harmful effects on the biosphere [3]. The cyanoiminothiazolidine substructure of the molecule (Figure 1) plays a key role in insecticidal activity [4][5][6]. It is of our prime interest to destroy the pharmacophore of the molecule via free radical reactions.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic study on thiacloprid transformation: Free radical reactions

Rózsa

Szabó

Schrantz

et al. 2017

Journal of Photochemistry and Photobiology A: Chemistry

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Highlights  • OH/eaqexhibits appreciable reactivity towards the insecticide thiacloprid  The majority of • OH attack the key cyanoiminothiazolidine pharmacophore  α-aminoalkyl, N-centred, α-(alkylthio)alkyl and >S •-OH radicals form on this moiety  One-electron reduction occurs at the pyridyl function yielding pyridinyl radicals  Destruction of pharmacologically important substructures is anticipated

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Section: Introductionmentioning

confidence: 99%

Mechanistic study on thiacloprid transformation: Free radical reactions

Rózsa

Szabó

Schrantz

et al. 2017

Journal of Photochemistry and Photobiology A: Chemistry

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“…QSAR approaches were applied to study the insecticidal activity of imidacloprid derivatives against the American cockroach, Periplaneta americana , the house‐fly, Musca domestica L ., the cowpea aphid, Aphis craccivora …”

Section: Introductionmentioning

confidence: 99%

An Approach to Identify New Insecticides Against Myzus Persicae. In silico Study Based on Linear and Non‐linear Regression Techniques

Crisan

Borota

Suzuki

et al. 2019

Molecular Informatics

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This paper is dedicated to Prof. Paola Gramatica on the occasion of her retirement.Abstract: Neonicotinoids are known to have high insecticidal potency, low mammalian toxicity and relatively tough activity for the development of resistance against aphids. A series of guadipyr insecticides, active against Myzus persicae was engaged in silico studies, based on Multiple Linear Regression (MLR), Partial Least Squares regression (PLS), Artificial Neural Networks (ANN), Support Vector Machine (SVM) and Pharmacophore modeling. Robust and predictive models were built using correlations between the insectici-dal profile, expressed by experimental pLC 50 values, and molecular descriptors, calculated from the energy optimized structures. Four new potential insecticides active against Myzus persicae and their predicted pLC 50 toxicity values were reported for the first time. The models presented here can be used as an approach in the screening and prioritization of chemicals in a scientific and regulatory frame and for toxicity prediction.

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“…The urgent need for the development of a new insecticide is related to the phenomenon of insecticide-resistant cases of pests. In this regard, several computational approaches were applied to study the insecticidal activity of neonicotinoids [10][11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Insecticidal Activity Evaluation of Phenylazo and Dihydropyrrole-Fused Neonicotinoids Against Cowpea Aphids Using the MLR Approach

Funar-Timofei¹,

Bora²

2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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This paper presents a Quantitative Structure-Activity Relationship (QSAR) study of a series of 24 dihydropyrrole-fused and phenylazo neonicotinoid derivatives, with insecticidal activity tested against Cowpea aphids (Aphis craccivora). In this regard, the conformational search ability of the OMEGA software was employed to model neonicotinoid conformer ensembles, using molecular mechanics calculations based on the 94s variant of the Merck Molecular force field (MMFF94). The minimum energy conformers were used to calculate structural descriptors, which were further related to the insecticidal activity (pLC50 values), using the multiple linear regression (MLR) approach. The genetic algorithm was used for variable selection and several criteria for internal and external model validation. A robust model (r2 = 0.880, r2adj = 0.855, q2LOO = 0.827, s = 0.2098, F = 34.295) with predictive power (concordance correlation coefficient (CCC)ext = 0.945, r2m= 0.824) was obtained, using the QSARINS software. The developed model can be confidently used for the prediction of the insecticidal activity of new chemicals, saving a substantial amount of time and money.

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Insecticidal and neuroblocking potencies of variants of the thiazolidine moiety of thiacloprid and quantitative relationship study for the key neonicotinoid pharmacophore

Cited by 18 publications

References 38 publications

Mechanistic study on thiacloprid transformation: Free radical reactions

Mechanistic study on thiacloprid transformation: Free radical reactions

An Approach to Identify New Insecticides Against Myzus Persicae. In silico Study Based on Linear and Non‐linear Regression Techniques

Insecticidal Activity Evaluation of Phenylazo and Dihydropyrrole-Fused Neonicotinoids Against Cowpea Aphids Using the MLR Approach

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