isoproturon structure

2022.07.31
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isoproturon structure

Mineralization of soil-aged isoproturon and isoproturon metabolites by Sphingomonas sp.

The role of exact exchange,, A. D. Becke, Density-functional exchange-energy approximation with correct asymptotic behavior,, C. Lee, W. Yang, and R. G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,, R. Krishnan, J. S. Binkley, R. Seeger, and J. Real, Removal of phenylurea herbicides from waters by using chemical oxidation treatments,, M. Kaur, A. K. Malik, and B. Singh, Determination of phenylurea herbicides in tap water and soft drink samples by HPLC-UV and solid-phase extraction,, J. M. Sanchis-Mallols, S. Sagrado, M. J. Medina-Hernndez, R. M. Villanueva Camaas, and E. Bonet-Domingo, Determination of phenylurea herbicides in drinking waters by HPLC and solid phase extraction,, N. Badawi, S. Rnhede, S. Olsson et al., Metabolites of the phenylurea herbicides chlorotoluron, diuron, isoproturon and linuron produced by the soil fungus, M. Carrier, M. Besson, C. Guillard, and E. Gonze, Removal of herbicide diuron and thermal degradation products under Catalytic Wet Air Oxidation conditions,.

A selective, systemic herbicide used to control annual grasses and broadleaf ; weeds in ce Effects of the pesticides captan, deltamethrin, isoproturon, and pirimicarb on the microbial community of a freshwater sediment.

Determination of a suitable sterilization method for soil in isoproturon biodegradation studies. In this sense, an advantage of the theoretical quantum methods resides in the fact that the electronic properties of the molecules may be calculated with enough accuracy, at the molecular level, to explain adequately the experimental behavior. Last result suggests that linuron is the most stable specie of this set of herbicides, while isoproturon result to be the most reactive. The Fukui function, equation (5), can be evaluated by using a finite difference approximation. The optimal conformations of isoproturon, chlorotoluron, diuron, and linuron were subjected to full geometry optimization in the gas phase employing the hybrid functional B3LYP [5759] and the basis set 6-311++G(2d,2p) [60, 61].

We consider that this kind of study will contribute to get a better understanding of the chemical behavior in aqueous media of these PHUs herbicides. From Figure 5, observe that for isoproturon the more reactive sites to electrophilic, nucleophilic, or free radical attacks are located interchangeably on 11C. Nevertheless, only few theoretical studies have analyzed the electronic properties of isoproturon, diuron, linuron, and chlorotoluron. Technology, Office of Data Metallothionein induction in the aquatic oligochaete Tubifex tubifex exposed to the herbicide isoproturon. The isoproturon, diuron, linuron, and chlorotoluron structures were optimized at the B3LYP/6-311++G (2d,2p) level in the gas phase. N,N-dimethyl-N'-(4-(1-methylethyl)phenyl)urea, WFD priority substance; Potential groundwater contaminant, Relevant Environmental Water Quality Standards, EU Directive 2008/105/EC EQS surface waters: annual average 0.3 g l; max measured 1.0 g l, Herbicide Resistance Classification (HRAC), Herbicide Resistance Classification (WSSA), Insecticide Resistance Classification (IRAC), Fungicide Resistance Classification (FRAC), Example manufacturers & suppliers of products using this active now or historically. The influence of lipophilicity and formulation on the distribution of pesticides in laboratory-scale sediment/water systems. Additional to the global reactivity parameters, it has been possible to define local reactivity parameters [52, 53], such as the Fukui Function () [54, 55]. Bond distances: 2C-4C = 1.39, 2C-5C = 1.37, 3C-6C = 1.40, 3C-7C = 1.36, 4C-7C = 1.39, 5C-6C = 1.40, 6C-11C = 1.43, 11C-12C = 1.50, 11C-16C = 1.50, 4C-20N = 1.40, 20N-22C = 1.39, 22C-23N = 1.37, 22C-32O = 1.24, 23N-28C = 1.46, 23N-24C = 1.46, N-H = 1.00, C-H = 1.09 in methyl groups, and C-H = 1.08 in the ring. Determination of the herbicide isoproturon in cereal grains and pasta by LC with LC/MS confirmation. If the file has been modified from its original state, some details such as the timestamp may not fully reflect those of the original file. P. A. Johnson, L. J. P. Bartolotti, W. Ayers, T. Fievez, and P. Geerlings, S.-B. Centers for Disease Control and Prevention National Institute for Occupational Safety and Health Education and Information Division, Occupational safety and health guideline for Diuron, February 2015, S. Malato, J. Cceres, A. R. Fernndez-Alba et al., Photocatalytic treatment of diuron by solar photocatalysis: evaluation of main intermediates and toxicity,, M. EL Madani, C. Guillard, N. Prol et al., Photocatalytic degradation of diuron in aqueous solution in presence of two industrial titania catalysts, either as suspended powders or deposited on flexible industrial photoresistant papers,, M. Carrier, C. Guillard, M. Besson, C. Hordes, and H. Chermette, Photocatalytic degradation of diuron: experimental analyses and simulation of HO radical attacks by density functional theory calculations,, P. A. K. Reddy, P. V. L. Reddy, V. M. Sharma, B. Srinivas, V. D. Kumari, and M. Subrahmanyam, Photocatalytic degradation of isoproturon pesticide on C, N and S doped TiO, F. Ruggieri, A. The global reactivity descriptors in the aqueous phase for isoproturon, chlorotoluron, diuron, and linuron were obtained at the MP2/6-311++G(2d,2p) level of theory. Additional to , , and , the global electrophilicity index can be written as [51]This index measures the susceptibility of chemical species to accept electrons, by which, low values of indicate the presence of good nucleophiles, while good electrophiles are characterized by higher values of [51]. Optical whole-cell biosensor using Chlorella vulgaris designed for monitoring herbicides. Global reactivity parameters indicate that isoproturon is the most reactive while linuron is the most stable. In the present work, we have analyzed the chemical reactivity of isoproturon, chlorotoluron, diuron, and linuron herbicides in the aqueous phase employing global and local reactivity parameters derived from the Density Functional Theory.

Modeling of an annular photocatalytic reactor for water purification: oxidation of pesticides. Data from NIST Standard Reference Database 69: The National Institute of Standards and Technology (NIST) Influence of kinetic sorption and diffusion on pesticide movement through aggregated soils. Here, it is interesting to highlight that the values of the Fukui Function found for diuron (see Figure 7) and linuron (see Figure 8) indicate that the more reactive sites are located on 4C, 7C, and 7C. A. Pople, and M. J. Frisch, MP2 energy evaluation by direct methods,. Also, it is possible to deduce that electrophilic attacks on 4C would cause the elimination of the metoxi-1-metilurea moiety.

Pesticides in rainwater in Flanders, Belgium: results from the monitoring program 1997-2001. It is important to mention that the values of the Fukui function are dependent on the scheme of charges used.

CopyCopied, InChI=1S/C12H18N2O/c1-9(2)10-5-7-11(8-6-10)13-12(15)14(3)4/h5-9H,1-4H3,(H,13,15) U.S. Department of Health and Human Sevices. Degradation of pesticides in biobeds: the effect of concentration and pesticide mixtures. The vibrational frequencies were computed to make sure that the stationary points were minima in the potential energy surface. Test system to establish mass balances for 14C-labeled substances in soil-plant-atmosphere systems under field conditions. An agrochemical is a substance that is used in agriculture or horticulture. with the development of data collections included in However, it is important to evaluate local reactivity descriptors as the condensed Fukui function to analyze the pinpoint distribution of the reactivity in the molecule in order to propose specific degradation mechanisms. The optimized molecules in the gas phase were further reoptimized at the B3LYP/6-311++G(2d,2p) level employing the PCM solvation model [62, 63], with the dielectric constant 78.5 for water at 25C. The purpose of the fee is to recover costs associated Finally, the optimized B3LYP/6-311++G(2d,2p) geometries were reoptimized employing the second order Mller Plesset theory (MP2) [64] with the basis set 6-311++G(2d,2p) in the aqueous phase. Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects,, M. Head-Gordon, J. A lysimeter experiment to investigate temporal changes in the availability of pesticide residues for leaching. Moreover, this kind of compounds requires several weeks to months for their removal from the environment [7], and they have been considered as priority hazardous substances [8]. Find compounds which contain this structure, Find compounds which resemble this structure, European Molecular Enzyme-linked immunosorbent assays based on rabbit polyclonal and rat monoclonal antibodies against isoproturon. EMBL-EBI, Wellcome Genome Campus, Hinxton, Cambridgeshire, CB10

The energy value of the vertical electronic affinity () can be calculated as , where and are the total ground-state energies in the neutral and singly charged configurations. The final atomic charges for isoproturon, chlorotoluron, diuron, and linuron were obtained in the framework of MP2 theory; in all calculations of these atomic charges, the option DENSITY = MP2 was used. However, it has been reported that AOPs may produce harmful intermediates [3032], while microbial and fungal degradation methods are unable to degrade completely these PHUs [29, 33]. Pesticide degradation in a 'biobed' composting substrate. Inhibits photosynthesis (photosystem II).

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Probably, Advanced Oxidation Processes (AOPs) [11, 1422] and microbial [2326] degradation methods are the preferred techniques to degrade this group of herbicides along with fungal degradation techniques [10, 2729]. Pesticide residues on the external surfaces of field-crop sprayers: environmental impact. Therefore, in this work we have analyzed the molecular reactivity of isoproturon, diuron, linuron, and chlorotoluron employing the global and local reactivity descriptors derived from DFT. 2021 by the U.S. Secretary of Commerce However, due to the discontinuity of the electron density with respect to the number of electrons (), this approximation leads to three types of Fukui Function for a system, namely, , , and for nucleophilic, electrophilic, and free radical attacks, respectively [52]. weeds in cereals, its use within the EU has been banned after September 2017 on the grounds of potential groundwater contamination and risks to aquatic life; there have also been concerns about its en Simultaneous multi-analyte determination of estrone, isoproturon and atrazine in natural waters by the RIver ANAlyser (RIANA), an optical immunosensor. Dihedral angle 2C-4C-10N-12C = 17.53, 10N-12C-13N-21O = 18.34. Influence of ageing of residues on the availability of herbicides for leaching. [40], respectively. at the th atomic site in the neutral (), anionic (), or cationic () chemical species. shall not be liable for any damage that may result from Size of this PNG preview of this SVG file: Add a one-line explanation of what this file represents, (SVG file, nominally 231 378 pixels, file size: 27 KB), http://commons.wikimedia.org/wiki/User:Codc, https://commons.wikimedia.org/w/index.php?title=File:Isoproturon_structure.svg&oldid=511835342, Creative Commons Attribution-ShareAlike License, {{Information |Description={{en|Structure of Isoproturone}} {{de|Struktur von Isoproturon}} |Source={{Own}} |Date={{subst:CURRENTYEAR}}-{{subst:CURRENTMONTH}}-{{subst:CURRENTDAY2}} |Author=~~~ |Other_versions= }} {{PD-chem}}.

A. Dihedral angle 12C-11C-6C-3C = 0.2, 2C-4C-20N-22C = 22.03.

Bond distances: 2C-4C = 1.40, 2C-5C = 1.39, 3C-6C = 1.40, 3C-7C = 1.39, 4C-7C = 1.40, 5C-6C = 1.39, 6C-19Cl = 1.74, 3C-20Cl = 1.74, 4C-10N = 1.40, 10N-12C = 1.37, 12C-18O = 1.23, 12C-13N = 1.40, 13N-21O = 1.42, 13N-14C = 1.46, 21O-22C = 1.44, N-H = 1.00, C-H = 1.09 in methyl groups, and C-H = 1.08 in the ring. A. Pople, Self-consistent molecular orbital methods. The typical parameters employed are the electronic chemical potential (), the electronegativity (), and hardness (), which are defined through the following equations [4147]:In these equations, , , and are the energy, number of electrons, and the external potential of the system, respectively. Thus, nucleophilic and free radical attacks on diuron and linuron would cause a substitution of the hydrogen atom on 7C, while electrophilic attacks on diuron and chlorotoluron would cause the elimination of the dimethylurea fragment. Evaluation and characterization of a commercial immunosorbent cartridge for the solid-phase extraction of phenylureas from aqueous matrices. Dihedral angle 2C-4C-10N-12C = 17.53, 10N-12C-13N-21O = 18.34. Specifically, the PUHs 3-(4-isopropylphenyl)-1,1-dimethyl urea (isoproturon), 3-(3,4-dichlorophenyl)-1,1-dimethylurea (diuron), 3-(3,4-diclorofenil)-1-metoxi-1-metilurea (linuron), and 3-(3-chloro-p-tolyl)-1,1-dimethylurea (chlorotoluron) are slowly degraded in water and are quite persistent [8, 9], and it is increasingly common to find their parent compounds and metabolites in groundwater in concentrations exceeding the drinking water threshold limit of 0.1gL1 [10, 11]. Copyright for NIST Standard Reference Data is governed by However, in aqueous conditions, the molecular basis for the initial degradation of these phenylurea herbicides remains unknown [35, 36]. In order to take into account the effect of solvation on the electronic properties of isoproturon, diuron, linuron, and chlorotoluron, the optimized structures in the gas phase were used as starting point to reoptimize them at the B3LYP/6-311++G(2d,2p) level without any symmetry constraints employing the PCM solvation model. A member of the class of phenylureas that is 1,1-dimethylurea substituted by a p-cumenyl group at position 3. I. Often supplied as a soluble concentrate that is mixed with water and used as a spray; New low dose formulations being considered for UK registration. In all cases a frequency analysis was applied to the optimized geometries to verify the stability criterion and in all cases the frequency values were positive. Chemical Reactivity of Isoproturon, Diuron, Linuron, and Chlorotoluron Herbicides in Aqueous Phase: A Theoretical Quantum Study Employing Global and Local Reactivity Descriptors, Centro de Investigaciones Qumicas, Universidad Autnoma del Estado de Hidalgo, Carretera Pachuca-Tulancingo Km 4.5, 42186 Mineral de la Reforma, HGO, Mexico, http://ec.europa.eu/environment/water/water-framework/priority_substances.htm, http://www.cdc.gov/niosh/docs/81-123/pdfs/0247.pdf, S. Giacomazzi and N. Cochet, Environmental impact of diuron transformation: a review,, S. R. Srensen, C. N. Albers, and J. Aamand, Rapid mineralization of the phenylurea herbicide diuron by, L. Vrielynck, C. Lapouge, S. Marquis, J. Kister, and N. Dupuy, Theoretical and experimental vibrational study of phenylurea: structure, solvent effect and inclusion process with the, F. Javier Benitez, C. Garcia, J. L. Acero, and F. J. Effects of exposure duration of herbicides on natural stream periphyton communities and recovery.

On the other hand, the atom 7C is susceptible to either nucleophilic or free radical substitutions. Metallothionein induction in aquatic oligochaete tubifex tubifex exposed to herbicide isoproturon. The general behavior of a molecular system may be analyzed employing the global reactivity parameters derived from the Density Functional Theory. Bond distances: 2C-4C = 1.40, 2C-5C = 1.39, 3C-6C = 1.40, 3C-7C = 1.39, 4C-7C = 1.40, 5C-6C = 1.40, 6C-20C = 1.50, 3C-19Cl = 1.76, 4C-10N = 1.41, 10N-12C = 1.39, 12C-18O = 1.24, 12C-13N = 1.36, 13N-24C = 1.45, 13N-14C = 1.46, N-H = 1.00, C-H = 1.09 in methyl groups, and C-H = 1.08 in the ring. Amylase induction during seed germination in isoproturon susceptible and resistant biotypes of Phalaris minor Retz. A comparative study,, F. L. Hirshfeld, Bonded-atom fragments for describing molecular charge densities,, J. Padmanabhan, R. Parthasarathi, U. Sarkar, V. Subramanian, and P. K. Chattaraj, Effect of solvation on the condensed Fukui function and the generalized philicity index,. We have calculated global and local DFT reactivity descriptors for isoproturon, diuron, linuron, and chlorotoluron herbicides at the MP2/6-311++G(2d,2p) level of theory. The chemical potential can be related to the escaping tendency of an electron and is characteristic of the molecular electronegativity [48], while has been related to the polarizability of the molecular system [49, 50].

Standard Reference Data Act. Climate change and decreasing herbicide persistence.