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Acta Crystallographica. Section E,... Jul 2010In the title compound, C(11)H(18)N(4)O(2) (systematic name: 2-dimethyl-amino-5,6-dimethyl-pyrimidin-4-yl N,N-dimethyl-carb-amate), the pyrimidine ring and dimethyl-amino...
In the title compound, C(11)H(18)N(4)O(2) (systematic name: 2-dimethyl-amino-5,6-dimethyl-pyrimidin-4-yl N,N-dimethyl-carb-amate), the pyrimidine ring and dimethyl-amino group are almost in the same plane, making a dihedral angle of 1.6 (1)°. The dihedral angle between the mean plane of the pyrimidine ring and that of the dimethyl-carbamate group is 83.42 (5)°. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds contribute to the stabilization of the packing.
PubMed: 21588312
DOI: 10.1107/S160053681002684X -
Pesticide Biochemistry and Physiology Jan 2022The predatory mite Neoseiulus californicus McGregor (Acari: Phytoseiidae) is an important natural enemy of phytophagous mites, and naturally established populations are...
The predatory mite Neoseiulus californicus McGregor (Acari: Phytoseiidae) is an important natural enemy of phytophagous mites, and naturally established populations are often found in apple orchards. However, insecticide applications to control pests cause side effects to non-target organisms such as N. californicus. Pirimicarb, a widely used carbamate insecticide in apple orchards, is generally considered a selective aphidicide, however, toxicity to beneficial insects and predatory mites has been reported. Furthermore, the molecular basis for this selectivity, if present in N. californicus, is still largely unknown. In this study, 8 field-collected N. californicus populations were investigated and showed up to 27-fold resistance compared to a susceptible laboratory population. Selection in the laboratory for 5 consecutive generations resulted in a 69-fold pirimicarb resistance. Although there were no significant difference in terms of the acetlycholinesterase (AChE) activity between susceptible and field-collected populations, the selected population exhibited a significantly higher AChE activity. In addition, gene copy number variation of acetylcholinesterase (ace) gene among populations was detected and ranged from 1.6 to 2.1-fold relative to the susceptible population. All field-collected populations, but not the selected population, had a significantly higher ace copy number compared to the susceptible population (t-test, p < 0.05). Molecular analysis of the target-site (AChE) revealed, for the first time, a phenylalanine to tryptophan substition at position 331 in AChE (Torpedo californica numbering), both in field-collected and the selected population, but not in the susceptible population. Last, the selected F5 population consumed significantly more Tetranychusurticae adults than the parental population. Together, the results of this study shed light on the molecular determinants of acaricide selectivity in predatory mites, and will contribute to a better design of an integrated mite management program, including the use of pesticide resistant N. californicus in apple orchards.
Topics: Acetylcholinesterase; Animals; Carbamates; DNA Copy Number Variations; Insecticide Resistance; Insecticides; Mites; Pest Control, Biological; Pyrimidines; Tetranychidae
PubMed: 34955177
DOI: 10.1016/j.pestbp.2021.104984 -
Pharmaceuticals (Basel, Switzerland) Mar 2023Carbamate pesticides are a risk to human well-being, and pirimicarb is the most widely employed carbamate insecticide. This ongoing investigation aimed to reveal its...
Carbamate pesticides are a risk to human well-being, and pirimicarb is the most widely employed carbamate insecticide. This ongoing investigation aimed to reveal its toxicity on neurobehavioral and reproductive function. The study was carried out on male Wistar rats by assessment of behavioral changes via experiments, such as the forced swim test and the elevated plus maze; determination of oxidative stress (checking parameters such as catalase activity, etc.); measurement of cortisol and testosterone serum titers, and IL-1β levels in the plasma and brain; and evaluation of histopathological lesions that induced pirimicarb after 28 days of gavage, specifically in the brain and testis. Traces of pirimicarb were analyzed in tissue extracts using LCMS/MS. At the same time, the beneficial and protective effect of EamCE ( monjauzeana Crude Extract) were tested. The outcomes showed considerable anxiety and depressive status, with an evident increase in cortisol and IL-1β titers and an important decrease in oxidative enzymes and testosterone. Significant histological lesions were also recorded. In addition, the LCMS/MS analysis affirmed the accumulation of pirimicarb in organ tissue from rats force-fed with pirimicarb. Conversely, EamCE demonstrated outstanding potential as a preventive treatment, restoring cognitive and physical performance, boosting fertility, enhancing antioxidant and anti-inflammatory activities and preserving tissue integrity. We concluded that pirimicarb has critical deleterious impacts on health, affecting the neuroimmune-endocrine axis, and EamCE has a general euphoric and preventive effect.
PubMed: 36986501
DOI: 10.3390/ph16030402 -
EFSA Journal. European Food Safety... Feb 2023On 26 August 2022, the European Commission asked EFSA to provide scientific and technical assistance according to Article 21(2) of Regulation (EC) No 1107/2009...
On 26 August 2022, the European Commission asked EFSA to provide scientific and technical assistance according to Article 21(2) of Regulation (EC) No 1107/2009 concerning the review of the approval of the active substance pirimicarb and to deliver a statement on whether the applicable approval criteria may still be considered fulfilled, taking into consideration the information submitted by the applicant and the assessment of the rapporteur Member State, Sweden and, where applicable, the results of a discussion with experts from Member States. The current statement contains a summary of the main findings of the assessment of the risks to consumers from the exposure to metabolites of pirimicarb through dietary intake, the risks to human health through non-dietary exposure and the acute risk to birds from the representative uses of pirimicarb assessed for the first approval and additionally, from the representative uses as submitted as part of the renewal of approval. Concerns are reported where identified.
PubMed: 36818643
DOI: 10.2903/j.efsa.2023.7807 -
Food Chemistry Feb 2022A novel deep eutectic solvent-based extraction and sulfur-doped carbon quantum dots (S-CQDs) serving as fluorescence probes to detect pirimicarb in cereals were...
A novel deep eutectic solvent-based extraction and sulfur-doped carbon quantum dots (S-CQDs) serving as fluorescence probes to detect pirimicarb in cereals were established. The deep eutectic solvent was synthesized using choline chloride and butanediol, achieving direct and efficient extraction of pirimicarb residue in the cereals. The fluorescence quenching of S-CQDs was caused by the electrostatic interaction between the negatively charged S-CQDs and positively charged thiocholine, which was the hydrolysate of acetylthiocholine. The fluorescence of S-CQDs was enhanced as the activity of acetylcholinesterase (AChE) was inhibited by pirimicarb, achieving the detection of pirimicarb in the cereal samples. The limit of detection (LOD) was 0.006 μg mL. The recovery ranged from 96.6% to 108.2%. This extraction and detection method of pirimicarb based on an environmentally friendly DES and S-CQD fluorescent sensor maintains good stability and convenience, offering a promising strategy for extracting and testing harmful substances in food samples.
Topics: Acetylcholinesterase; Carbamates; Edible Grain; Pyrimidines; Quantum Dots; Solvents
PubMed: 34662796
DOI: 10.1016/j.foodchem.2021.131360 -
Polymers Jan 2023An electrochemical sensor for the pesticide Pirimicarb (PMC) has been developed. A screen-printed electrode (SPCE) was used and modified with the conducting polymer poly...
An electrochemical sensor for the pesticide Pirimicarb (PMC) has been developed. A screen-printed electrode (SPCE) was used and modified with the conducting polymer poly (3,4-ethylenedioxythiophene) (PEDOT) and gold nanoparticles (AuNPs) to enhance electrochemical proprieties. Electrode characterizations were performed using scattering electron microscopy (SEM) and cyclic voltammetry (CV). With the SPCE/PEDOT:PSS/AuNPs modified electrode, a new peak at 1.0 V appeared in the presence of PMC related to the PMC oxidation. To elucidate the mechanism of PMC oxidation, Gas Chromatography-Mass Spectrometry (GC-MS), where two major peaks were identified, evidencing that the device can both detect and degrade PMC by an electro-oxidation process. Exploring this peak signal, it was possible the sensor development, performing detection from 93.81-750 µmol L, limits of quantification (LOQ) and detection (LOD) of 93.91 µmol L and 28.34 µmol L, respectively. Thus, it was possible to study and optimization of PMC degradation, moreover, to perform detection at low concentrations and with good selectivity against different interferents using a low-cost printed electrode based on graphite modified with conductive polymer and AuNPs.
PubMed: 36772040
DOI: 10.3390/polym15030739 -
Scientific Reports May 2024In this study, a sensitive and selective fluorescent chemosensor was developed for the determination of pirimicarb pesticide by adopting the surface molecular imprinting...
In this study, a sensitive and selective fluorescent chemosensor was developed for the determination of pirimicarb pesticide by adopting the surface molecular imprinting approach. The magnetic molecularly imprinted polymer (MIP) nanocomposite was prepared using pirimicarb as the template molecule, CuFeO nanoparticles, and graphene quantum dots as a fluorophore (MIP-CuFeO/GQDs). It was then characterized using X-ray diffraction (XRD) technique, Fourier transforms infrared (FT-IR) spectroscopy, scanning electron microscope (SEM), and transmission electron microscopy (TEM). The response surface methodology (RSM) was also employed to optimize and estimate the effective parameters of pirimicarb adsorption by this polymer. According to the experimental results, the average particle size and imprinting factor (IF) of this polymer are 53.61 nm and 2.48, respectively. Moreover, this polymer has an excellent ability to adsorb pirimicarb with a removal percentage of 99.92 at pH = 7.54, initial pirimicarb concentration = 10.17 mg/L, polymer dosage = 840 mg/L, and contact time = 6.15 min. The detection of pirimicarb was performed by fluorescence spectroscopy at a concentration range of 0-50 mg/L, and a sensitivity of 15.808 a.u/mg and a limit of detection of 1.79 mg/L were obtained. Real samples with RSD less than 2 were measured using this chemosensor. Besides, the proposed chemosensor demonstrated remarkable selectivity by checking some other insecticides with similar and different molecular structures to pirimicarb, such as diazinon, deltamethrin, and chlorpyrifos.
Topics: Pesticides; Carbamates; Quantum Dots; Molecularly Imprinted Polymers; Polymers; Spectrometry, Fluorescence; Graphite; Molecular Imprinting; Adsorption; Limit of Detection; Spectroscopy, Fourier Transform Infrared; Nanocomposites; Pyrimidines
PubMed: 38704412
DOI: 10.1038/s41598-024-60748-6 -
Environmental Science and Pollution... Jun 2019Insecticide spray in fruit gardens is a very common practice in different districts of Pakistan. These toxic sprays not only deteriorate the taste of fruit but also due...
Insecticide spray in fruit gardens is a very common practice in different districts of Pakistan. These toxic sprays not only deteriorate the taste of fruit but also due to wet deposition travel through soil, they reach groundwater via leaching process. In the present study, imidazolium-based ionic liquid ([Cim][CHNH]Br) and its cellulose acetate-supported membrane ([CA-Cim][CHNH]Br) was prepared and characterized using FTIR, XRD, and SEM. These materials are used as adsorbents for the removal of "Pirimicarb" (an insecticide from waste water). A closed batch at varying parameters, i.e., concentration and temperature as function of time, was conducted on UV-Vis spectrophotometer. Comparison of removal capacity exposed better (74%) adsorption trend by CA-IL membrane than ionic liquid (68%). Thermodynamic studies projected spontaneous process (-ΔG), favoring endothermic reaction (ΔH, ΔS). Kinetics supported pseudo-second order reaction while fitness of isothermic models (Langmuir, Freundlich, Temkin) proposed multistep intraparticle diffusion process.
Topics: Adsorption; Carbamates; Cellulose; Ionic Liquids; Ions; Kinetics; Pakistan; Pyrimidines; Temperature; Thermodynamics; Wastewater; Water Pollutants, Chemical
PubMed: 30980372
DOI: 10.1007/s11356-019-04681-6 -
Toxicology and Industrial Health Nov 2015We analyzed the aspects of lethality, genotoxicity, and cytotoxicity in the ten spotted live-bearer exposed under laboratory conditions to the pirimicarb-based...
We analyzed the aspects of lethality, genotoxicity, and cytotoxicity in the ten spotted live-bearer exposed under laboratory conditions to the pirimicarb-based formulation Patton Flow® (50% active ingredient (a.i.)). Acute effects were evaluated using different end points for lethality, genotoxicity, and cytotoxicity. Median lethal concentration (LC50) estimation was employed as a bioassay for lethality, whereas micronucleus (MN) induction and alterations in erythrocyte/erythroblast frequency were used as end points for genotoxicity and cytotoxicity, respectively. Results demonstrated an LC5096h value of 88 mg/L. Patton Flow® increased the MN frequency in fish erythrocytes after 48 h of exposure at a concentration of 66 mg/L, whereas a concentration range of 22-66 mg/L was able to exert the same genotoxic effect at 96 h of treatment. Furthermore, cytotoxicity was also observed by alterations in erythrocyte/erythroblast frequencies within the concentration range of 22-66 mg/L, regardless of the exposure time. Our current observations provide evidence that Patton Flow® (50% a.i.) should be considered a clear lethal, cytotoxic, and genotoxic agent on Cnesterodon decemmaculatus. Thus, repeated applications of this carbamic insecticide can enter the aquatic environment and exert deleterious effects on aquatic organisms other than the evaluated species C. decemmaculatus.
Topics: Animals; Carbamates; Cyprinodontiformes; DNA Damage; Erythrocytes; Fresh Water; Insecticides; Lethal Dose 50; Micronucleus Tests; Pyrimidines
PubMed: 23625907
DOI: 10.1177/0748233713486958