Monocrotophos: dimethyl (E)-1-methyl-2-(methylcarbamoyl)ethenyl phosphate

Abstract

In the title compound, C7H14NO5P, the phosphate group displays rotational disorder of three O atoms with an occupancy ratio of 0.832 (6):0.167 (6). The dihedral angle between the acryl­amide group and PO2 plane of the phosphate group is 75.69 (7)°. In the crystal, inter­molecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules.

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

“…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 .…”

“…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.…”

“…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.…”

“…The crystal structures of simazine [ 9 ], monocrotophos [ 10 ], dimethoate [ 11 ], and acetamiprid [ 12 ] were retrieved from The Cambridge Crystallographic Data Centre (CCDC) (CSD IDs: KUYXIM, ULEJIF, IPCPYB, HANBAA). The remaining pesticides structures were generated by drawing using the MacroModel version 8 software (Schrodinger, Cambridge, MA, USA) [ 75 ].…”

“…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.…”