Crystal and molecular structures of organophosphorus insecticides. 13. S-Isopropyl O-methyl O-(3,5,6-trichloro-2-pyridyl) phosphoramidothioate and dimethoate

Lapp, R. L.; Jacobson, R. A.

doi:10.1021/jf60230a051

Cited by 6 publications

(8 citation statements)

References 19 publications

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“…[16,17] The initial structure of DMT was obtained from the Cambridge Crystallographic Data Base (Refcode: IPCPYB). [18] Thermodynamic data were determined analytically with the standard statistical thermodynamic methods implemented in that package at 298.15 K and 1.0 atm. Vibrational wavenumbers were computed by determining the second derivatives of the energy with respect to the Cartesian nuclear coordinates.…”

Section: Methodsmentioning

confidence: 99%

Surface‐enhanced Raman spectra of dimethoate and omethoate

Guerrini

Sánchez-Cortés

Cruz

et al. 2010

J Raman Spectroscopy

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Surface-enhanced Raman scattering (SERS) spectra are presented and analyzed for two important organophosphate pesticides, dimethoate (DMT) and omethoate (OMT). Very detailed SERS spectra were obtained by aggregated Ag hydrosols, both in aqueous suspension and dried on a glass substrate. The SERS and ordinary Raman spectra of DMT do not resemble each other, suggesting that a chemical reaction immediately occurs when DMT is adsorbed onto the metal surface. We propose that the reaction product is OMT, which is the oxygen analog of DMT, on the basis of the Raman and SERS spectra of OMT. Further support is derived from the calculated Raman spectra of DMT and OMT. Minor wavenumber and intensity differences that are observed between the SERS spectra of DMT reaction product and those of OMT could be related to different metal/adsorbate interaction modes. The results can be useful in the development of new analytical methods for the determination of pesticide residues in food.

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Section: Methodsmentioning

confidence: 99%

Surface‐enhanced Raman spectra of dimethoate and omethoate

Guerrini

Sánchez-Cortés

Cruz

et al. 2010

J Raman Spectroscopy

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“…Conformational analysis (CA) studies are herein reported for simazine [ 9 ], monocrotophos [ 10 ], dimethoate [ 11 ], and acetamiprid [ 12 ] ( Table 3 ), as pesticides with known crystal structures, as well as for atrazine and carbofuran, as pesticides that exert the highest acute toxicity ( Table 4 ). To avoid redundancy, applied studies to the other pesticides are reported as Supplementary Material .…”

Section: Resultsmentioning

confidence: 99%

“…To avoid redundancy, applied studies to the other pesticides are reported as Supplementary Material . The crystal structures of simazine [ 9 ], monocrotophos [ 10 ], dimethoate [ 11 ], and acetamiprid [ 12 ] ( Table 3 , Tables S1–S3 ) were used as starting conformational geometries for the CA. For pesticides without experimental data ( Table 4 , Tables S1–S3 ), starting conformations were built from scratch and energy minimized.…”

Section: Resultsmentioning

confidence: 99%

“…CA results for simazine [ 9 ], monocrotophos [ 10 ], dimethoate [ 11 ], and acetamiprid [ 12 ] are reported in Table 3 . MM3 and AMBER94 could not be applied to all of the crystallized pesticides as the needed parameters for the optimization were not available.…”

Section: Resultsmentioning

confidence: 99%

“…This report considers the pharmacology of common agricultural pesticides used in particular in the Western Balkans region [ 7 , 8 ]: atrazine, simazine, propazine, carbofuran, monocrotophos, dimethoate, carbaryl, tebufenozide, imidacloprid, acetamiprid, diuron, monuron, and linuron ( Table 1 ). Despite their widespread usage, experimental crystal structures deposited at Cambridge Crystallographic Data Centre (CCDC) are available only for simazine [ 9 ], monocrotophos [ 10 ], dimethoate [ 11 ], and acetamiprid [ 12 ], highlighting the poor availability of either ligand-based (CCDC deposition) or structure-based (Protein Data Bank (PDB) deposition) information about these compounds.…”

Section: Introductionmentioning

confidence: 99%

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The Targeted Pesticides as Acetylcholinesterase Inhibitors: Comprehensive Cross-Organism Molecular Modelling Studies Performed to Anticipate the Pharmacology of Harmfulness to Humans In Vitro

et al. 2018

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Commercially available pesticides were examined as Mus musculus and Homo sapiens acetylcholinesterase (mAChE and hAChE) inhibitors by means of ligand-based (LB) and structure-based (SB) in silico approaches. Initially, the crystal structures of simazine, monocrotophos, dimethoate, and acetamiprid were reproduced using various force fields. Subsequently, LB alignment rules were assessed and applied to determine the inter synaptic conformations of atrazine, propazine, carbofuran, carbaryl, tebufenozide, imidacloprid, diuron, monuron, and linuron. Afterwards, molecular docking and dynamics SB studies were performed on either mAChE or hAChE, to predict the listed pesticides’ binding modes. Calculated energies of global minima (Eglob_min) and free energies of binding (∆Gbinding) were correlated with the pesticides’ acute toxicities (i.e., the LD50 values) against mice, as well to generate the model that could predict the LD50s against humans. Although for most of the pesticides the low Eglob_min correlates with the high acute toxicity, it is the ∆Gbinding that conditions the LD50 values for all the evaluated pesticides. Derived pLD50 = f(∆Gbinding) mAChE model may predict the pLD50 against hAChE, too. The hAChE inhibition by atrazine, propazine, and simazine (the most toxic pesticides) was elucidated by SB quantum mechanics (QM) DFT mechanistic and concentration-dependent kinetic studies, enriching the knowledge for design of less toxic pesticides.

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Interaction of some organophosphorus pesticides with vermiculite

Sánchez‐Camazano¹,

Sánchez-Martín²

1987

Applied Clay Science

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Crystal and molecular structures of organophosphorus insecticides. 13. S-Isopropyl O-methyl O-(3,5,6-trichloro-2-pyridyl) phosphoramidothioate and dimethoate

Cited by 6 publications

References 19 publications

Surface‐enhanced Raman spectra of dimethoate and omethoate

Surface‐enhanced Raman spectra of dimethoate and omethoate

The Targeted Pesticides as Acetylcholinesterase Inhibitors: Comprehensive Cross-Organism Molecular Modelling Studies Performed to Anticipate the Pharmacology of Harmfulness to Humans In Vitro

Interaction of some organophosphorus pesticides with vermiculite

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