InChI=1S/C9H12N2O/c1-11(2)9(12)10-8-6-4-3-5-7-8/h3-7H,1-2H3,(H,10,12) |
XXOYNJXVWVNOOJ-UHFFFAOYSA-N |
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environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
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photosystem-II inhibitor
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
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photosystem-II inhibitor
agrochemical
An agrochemical is a substance that is used in agriculture or horticulture.
herbicide
A substance used to destroy plant pests.
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View more via ChEBI Ontology
1,1-dimethyl-3-phenylurea
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1-phenyl-3,3-dimethylurea
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NIST Chemistry WebBook
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3-phenyl-1,1-dimethylurea
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NIST Chemistry WebBook
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fenuron
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UniProt
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N,N-dimethyl-N'-phenylurea
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IUPAC
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N-Phenyl-N',N'-dimethylurea
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ChemIDplus
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PDU
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PPDB
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Amicure UR
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ChemIDplus
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Croptex Chrome
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ChemIDplus
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Croptex Ruby
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ChemIDplus
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Dibar
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ChemIDplus
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Dozer
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ChEBI
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Dybar
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ChemIDplus
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Electrum
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ChemIDplus
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Falisilvan
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ChemIDplus
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Fenidim
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ChemIDplus
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Fenidin
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ChemIDplus
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Herbon Yellow
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ChemIDplus
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Omicure 94
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ChemIDplus
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Quintex
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ChemIDplus
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313
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PPDB
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C11224
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KEGG COMPOUND
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CPD-23258
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MetaCyc
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fenuron
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Alan Wood's Pesticides
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View more database links |
101-42-8
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CAS Registry Number
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NIST Chemistry WebBook
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101-42-8
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CAS Registry Number
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ChemIDplus
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2208535
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Reaxys Registry Number
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Reaxys
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Abraham DA, Vasantha VS (2020) Hollow Polypyrrole Composite Synthesis for Detection of Trace-Level Toxic Herbicide. ACS omega 5, 21458-21467 [PubMed:32905395] [show Abstract] In this work, we successfully demonstrated the fabrication of a chemical sensor for toxic 1,1-dimethyl-3-phenylurea (fenuron) by using a hollow polypyrrole composite film. Here, we studied the interaction between negatively charged phosphate anions enclosed in the film with positively charged nitrogen atoms present in the fenuron. The electrochemical response of the film was characterized by cyclic voltammetry in which, interestingly, we observed that the bigger alkyl aryl sulphonate ions were replaced by smaller phosphate ions with the creation of hollow/pore composite films. Confirmation for ion replacement in the film and porosity of the film were studied by elemental analysis and field emission scanning electron microscopy, respectively. The tuning of hydrophilic to hydrophobic nature of the hollow composite film was tested by the wettability test (contact angle measurement). The electrocatalytic materials, as well as the fenuron sensing conditions such as pH and film thickness, were wisely optimized on glassy carbon (GC) electrodes for better performance. We can enhance the fenuron sensitivity by over 5 times as compared to that on the GC substrate. To our knowledge, this is the first electrochemical fenuron sensor based on a hollow polymer film by differential pulse voltammetry which can detect lower concentrations and show quick response compared to other reports. This method has potential applications in the electrochemical sensing platform with good sensitive and selective analysis in agriculture groundwater samples. | Ali I, Alharbi OML, ALOthman ZA, Al-Mohaimeed AM, Alwarthan A (2019) Modeling of fenuron pesticide adsorption on CNTs for mechanistic insight and removal in water. Environmental research 170, 389-397 [PubMed:30623886] [show Abstract] Inexpensive multi-walled carbon nanotubes (MCNTs) were prepared with 10-40 nm particle sizes and 9.0 m2g-1 surface area. Fenuron pesticide was removed in water using these CNTs with 100.0 µgL-1 concentration, 60 min contact time, 2.0 g L-1 dose, 7.0 pH, and 25 °C. 90% removal of fenuron pesticide was achieved. Adsorption data obeyed Tempkin, Freundlich, Langmuir and Dubinin-Radushkevich models. The standard free energies values of fenuron pesticide adsorption were -11.89, -11.59, -11.55 kJ mol-1. The values of enthalpy and entropy were -9.12 kJmol-1 and -26.61 × 10-3 kJ mol-1 K. The negative values of free energy showed speedy adsorption of fenuron pesticide on CNTs. The supramolecular mechanism of fenuron adsorption onto CNTs was fixed by simulation studies and the binding energy and binding affinity of fenuron with CNTs were - 6.5 kcal mol-1 and 5.85 × 104 M-1, respectively. There were one π-σ, seven π-π stacked, one π-π T-shaped, and three π-alkyl type of hydrophobic interactions between fenuron and carbon nanotube. These results clearly indicated the physical nature of the adsorption. The method is speedy, cost-effective, efficient and repeatable. Therefore, the established adsorption method is appropriate for adsorption of fenuron pesticide in waters. | Haruna K, Kumar VS, Sheena Mary Y, Popoola SA, Thomas R, Roxy MS, Al-Saadi AA (2019) Conformational profile, vibrational assignments, NLO properties and molecular docking of biologically active herbicide1,1-dimethyl-3-phenylurea. Heliyon 5, e01987 [PubMed:31304416] [show Abstract] 1,1-Dimethyl-3-phenylurea (known as fenuron) which is a phenyl urea-based widely used herbicide exhibits interesting structural and conformational properties and a notable biological activity. A detailed analysis on the vibrational, molecular and electronic characteristics of fenuron has been carried out. Potential energy scans (PESs) performed at the B3LYP/6-311++G(d,p) level of theory predicted two possible minima corresponding to the optimized anti and synforms resulting from the internal rotation about the N-C bond. The presence of an auxochrome together with the interaction with DMSO solvent exhibited a blue shift corresponding to the C=O orbitals. Delocalization of HOMO and LUMO orbital facilitated the charge transfer effect in the molecule. The calculated HOMO-LUMO energies, chemical potential, energy gap and global hardness suggested a low softness value for the compound while its biological activity was described by the value of electrophilicity. Chlorine substitution in the phenyl ring influenced the orbital delocalization for ortho and para substitutions but that of meta remained unaffected. NLO properties were noticed to increase due to chlorine substitution in the parent molecule. The docking results suggested that the compound exhibits an inhibitory activity against mitochondrial ubiquinol-cytochrome-c reductase and can be developed as a potential anticancer agent. | Diaw PA, Mbaye OMA, Thiaré DD, Oturan N, Gaye-Seye MD, Coly A, Le Jeune B, Giamarchi P, Oturan MA, Aaron JJ (2019) Combination of photoinduced fluorescence and GC-MS for elucidating the photodegradation mechanisms of diflubenzuron and fenuron pesticides. Luminescence : the journal of biological and chemical luminescence 34, 465-471 [PubMed:30784165] [show Abstract] Diflubenzuron (DFB) and fenuron (FEN) are benzoylurea and phenylurea pesticides, widely used in Senegal, that do not exhibit any natural fluorescence, but can be determined by means of photoinduced fluorescence (PIF) methods. Photodegradation of DFB and FEN yielded a number of fluorescent and non-fluorescent photoproducts. For both pesticides, at least 10 photoproducts were detected and identified by gas chromatography-mass spectrometry (GC/MS). To identify the formed fluorescent DFB and FEN photoproducts, their fluorescence spectra were compared with those of standard compounds, including phenol and p-hydroxyaniline. | Barbari K, Delimi R, Benredjem Z, Saaidia S, Djemel A, Chouchane T, Oturan N, Oturan MA (2018) Photocatalytically-assisted electrooxidation of herbicide fenuron using a new bifunctional electrode PbO2/SnO2-Sb2O3/Ti//Ti/TiO2. Chemosphere 203, 1-10 [PubMed:29604424] [show Abstract] The degradation of the herbicide fenuron was investigated using a new porous bifunctional electrode where the electrooxidation takes place on one side and the photocatalysis on the other side. The characterization of the synthetized bifunctional electrode (PbO2/SnO2-Sb2O3/Ti//Ti/TiO2) was performed by scanning electron microscopy, energy dispersive X-ray spectrometry and X-ray diffraction analysis and showed that the anodic side (Ti/SnO2-Sb2O3/PbO2) is covered with a tetragonal β-PbO2 film and that the photocatalytic side (Ti/TiO2) consists of an anatase phase of TiO2. The single application of electrooxidation achieved 87.8% fenuron degradation and 84.1% chemical oxygen demand (COD) removal while heterogeneous photocatalysis resulted in only 59.2% and 39.7% fenuron concentration decay and COD removal, respectively. On the other hand, the photocatalytically-assisted electrooxidation (photo-electrooxidation) performed on the bifunctional electrode provided higher performances of fenuron degradation (97.5%) and mineralization (97.4%). Investigation of operating parameters highlighted the positive effect of increase in current density. Conversely, an increase in fenuron concentration led to a decrease in degradation rate and COD removal. It was also found that the COD removal and mineralization efficiency are higher in a neutral medium. | Kribéche Mel A, Mechakra H, Sehili T, Brosillon S (2016) Oxidative photodegradation of herbicide fenuron in aqueous solution by natural iron oxide α-Fe2O3, influence of polycarboxylic acids. Environmental technology 37, 172-182 [PubMed:26102217] [show Abstract] The photodegradation of the herbicide fenuron (1,1-dimethyl-3-phenylurea) by using a natural iron oxide (NIO), α-Fe2O3, in aqueous solution at acidic pH has been undertaken. The NIO was characterized by the Raman spectroscopy method. The degradation pathways and the formation of degradation products were studied. A high-pressure mercury lamp and sunlight were employed as light source. Fenuron photodegradation using NIO with oxalic acid followed the pseudo-first-order kinetics, the optimal experimental conditions were [oxalic acid]0 = 10(-3) M and [NIO] = 0.1 g L(-1) at pH 3. A UVA/NIO/oxalic acid system led to a low fenuron half-life (60 min). The results were even better when solar light is used (30 min). The variables studied were the doses of iron oxide, of carboxylic acids, the solution pH and the effect of sunlight irradiation. The effects of four carboxylic acids, oxalic, citric, tartaric and malic acids, on the fenuron photodegradation with NIO have been investigated, oxalic acid was the most effective carboxylic acid used at pH 3. A similar trend was observed for the removal of total organic carbon (TOC), 75% of TOC was removed. The analytical study showed many aromatic intermediates, short-chain carboxylic acids and inorganic ion. | Fabbri D, Minella M, Maurino V, Minero C, Vione D (2015) Photochemical transformation of phenylurea herbicides in surface waters: a model assessment of persistence, and implications for the possible generation of hazardous intermediates. Chemosphere 119, 601-607 [PubMed:25128892] [show Abstract] This work models the phototransformation kinetics in surface waters of five phenylurea herbicides (diuron, fenuron, isoproturon, metoxuron and chlortoluron), for which important photochemical parameters are available in the literature (direct photolysis quantum yields and reaction rate constants with ·OH, CO3(-·) and the triplet states of chromophoric dissolved organic matter, (3)CDOM*). Model calculations suggest that isoproturon and metoxuron would be the least photochemically persistent and diuron the most persistent compound. Reactions with ·OH and (3)CDOM* would be the main phototransformation pathways for all compounds in the majority of environmental conditions. Reaction with CO3(-) could be important in waters with low dissolved organic carbon (DOC), while direct photolysis would be negligible for fenuron, quite important for chlortoluron, and somewhat significant for the other compounds. The direct photolysis of metoxuron and diuron is known to increase toxicity, and such a photoreaction pathway would be enhanced at intermediate DOC values (1-4 mg C L(1)). The reaction between phenylureas and ·OH is known to produce toxic intermediates, differently from (3)CDOM*. Therefore, the shift of reactivity from ·OH to (3)CDOM* with increasing DOC could reduce the environmental impact of photochemical transformation. | Mazellier P, Busset C, Delmont A, De Laat J (2007) A comparison of fenuron degradation by hydroxyl and carbonate radicals in aqueous solution. Water research 41, 4585-4594 [PubMed:17675205] [show Abstract] A comparative study of the transformation of the herbicide fenuron (1,1-dimethyl-3-phenylurea) by hydroxyl radicals and carbonate radicals in aqueous solution (pH 7.2-phosphate buffer) has been undertaken. Hydroxyl radical was generated by the well-known photolysis of hydrogen peroxide at 254 nm and carbonate radical was formed by photolysis of Co(NH(3))(5)CO(3)(+) at 254 nm. Competitive kinetic experiments were performed with atrazine used as the main competitor for both processes. Accordingly, the second-order rate constant of reaction between fenuron and carbonate radical was found to be (7-12+/-3)x10(6)M(-1)s(-1) [(7+/-1)x10(9)M(-1)s(-1) for hydroxyl radical]. The formation of degradation products was studied by LC-MS in the two cases and a comparison has been performed. The reaction with carbonate radical leads to the formation of a quinone-imine derivative which appears as the major primary product together with ortho and para hydroxylated compounds. These two compounds represent the major products in the reaction with hydroxyl radicals. The reaction of both radicals also leads to the transformation of the dimethylurea moiety. | Hermosin MC, Calderón MJ, Aguer JP, Cornejo J (2001) Organoclays for controlled release of the herbicide fenuron. Pest management science 57, 803-809 [PubMed:11561405] [show Abstract] Organoclays were assayed as matrices in which to associate herbicides, with the aim of decreasing product losses that could give rise to water contamination from agricultural activities. Fenuron was selected as model of a very mobile and highly water-soluble herbicide. Two different organoclays of high (A-HDT) and low (H-C18) reversible fenuron sorption were selected. Herbicide-organoclay complexes were prepared from the two organoclays and with two different fenuron contents (20 and 40 g AI kg-1) and two different mixing times, so as to form a series of weak and strong complexes. The release of fenuron from those complexes into water and water/soil suspensions gave values of T50 (time to release 50% of the fenuron content) ranging from 0.3 min to 2400 h. The total fenuron released in these closed systems ranged from 48 to 80% of the fenuron in the complex. The organoclay type (high or low sorptivity) had the greatest influence on fenuron release, followed by the strong or weak complex, suggesting that herbicide-organoclay interactions are the main factors controlling release. Soil column leaching experiments showed fenuron-organoclay complexes to be effective in reducing the peak herbicide concentration in the leachate to a half (6 microns) or a quarter (3 microns) of that obtained from the free technical compound (12 microns). Herbicide lost through leaching was reduced from 78% for the free technical fenuron to 50-30%, depending on the organoclay used as carrier and the strength of the complex. Bioassay with ryegrass showed that the weak fenuron/H-C18 complex (40 g AI kg-1) gave the same herbicidal activity as technical fenuron. The potential suitability of low-sorptive organoclays for conferring slow-release properties on the fenuron complex has been demonstrated. | Aguer JP, Hermosin MC, Calderon MJ, Cornejo J (2000) Fenuron sorption on homoionic natural and modified smectites. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 35, 279-296 [PubMed:10808993] [show Abstract] The adsorption isotherms of fenuron (1,1-dimethyl-3-phenylurea) on three smectites (SWy and SAz montmorillonites and SH hectorite) differing in their layer charge (SH | Shipman RD (1987) Fenuron converts low-grade hardwoods to Japanese larch. Proceedings of the ... annual meeting - Northeastern Weed Science Society. 41, 179-182 [Agricola:IND87057830] | Voloshina LT (1985) [Embryotropic effect of fenuron]. Vrachebnoe delo103-105 [PubMed:3992974] | Motuzinskiĭ NF, Rakitskiĭ VN, Perlovskaia ED (1982) [Data on establishing the maximum permissible levels for the fenuron content of forest vegetable food products]. Gigiena i sanitariia82-84 [PubMed:7084728] | Mazzocchi PH, Rao MP (1972) Photolysis of 3-(p-chlorophenyl)-1,1-dimethylurea (monuron) and 3-phenyl-1,1-dimethylurea (fenuron). Journal of agricultural and food chemistry 20, 957-959 [PubMed:5057445] |
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