dichlobenil

2,6-dichlorocyanobenzene

CAS: 1194-65-6 C7 H3 Cl2 N MW: 172.01191000

Identification

Namedichlobenil
IUPAC2,6-dichlorobenzonitrile
CAS Number1194-65-6
EINECS214-787-5
FDA UNIIN42NR4196R
Molecular FormulaC7 H3 Cl2 N
Molecular Weight172.01191000
MDL NumberMFCD00001781
Nikkaji NumberJ3.365K
Beilstein1909167
XlogP32.70 (est)

Regulatory

Physical Properties

Appearance white solid (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 144.50 °C. @ 760.00 mm Hg
Boiling Point 270.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.001010 mmHg @ 25.00 °C. (est)
Flash Point 260.00 °F. TCC ( 126.80 °C. ) (est)
logP (o/w) 2.740
Soluble in water, 21.2 mg/L @ 25 °C (exp)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityoral-guinea pig LD50 681 mg/kg
Dermal Toxicityskin-mouse LD > 200 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryherbicides / pesticides
Recommendation for dichlobenil usage levels up tonot for fragrance use.
Recommendation for dichlobenil flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

Synonyms

benzonitrile, 2,6-dichloro- casoron G casoron G-10 decabane 1,3- dichloro-2-cyanobenzene 2,6- dichlorobenzenecarbonitrile 2,6- dichlorobenzoic acid nitrile 2,6- dichlorobenzonitrile 2,6- dichlorocyanobenzene 2,6- dichlorophenyl cyanide dyclomec niagara 5996 norosac surfassol PubMed: Early cell-wall modifications of maize cell cultures during habituation to dichlobenil. PubMed: Sensitivity of Aspergillus nidulans to the cellulose synthase inhibitor dichlobenil: insights from wall-related genes' expression and ultrastructural hyphal morphologies. PubMed: Degradation of three benzonitrile herbicides by Aminobacter MSH1 versus soil microbial communities: pathways and kinetics. PubMed: Ensuring selectivity and sensitivity by timed- and ultra-selective reaction monitoring during gas chromatography-tandem mass spectrometric determination of pesticides. PubMed: Dichlobenil and 2,6-dichlorobenzamide (BAM) dissipation in topsoil and deposits from groundwater environment within the boreal region in southern Finland. PubMed: Mechanisms of permanent loss of olfactory receptor neurons induced by the herbicide 2,6-dichlorobenzonitrile: effects on stem cells and noninvolvement of acute induction of the inflammatory cytokine IL-6. PubMed: Emerging pesticide metabolites in groundwater and surface water as determined by the application of a multimethod for 150 pesticide metabolites. PubMed: Enhanced resistance to the cellulose biosynthetic inhibitors, thaxtomin A and isoxaben in Arabidopsis thaliana mutants, also provides specific co-resistance to the auxin transport inhibitor, 1-NPA. PubMed: Purification and characterization of a soluble β-1,4-glucan from bean (Phaseolus vulgaris L.)-cultured cells dehabituated to dichlobenil. PubMed: Optimization of an immunoassay of 2,6-dichlorobenzamide (BAM) and development of regenerative surfaces by immunosorbent modification with newly synthesised BAM hapten library. PubMed: Biotransformation of benzonitrile herbicides via the nitrile hydratase-amidase pathway in rhodococci. PubMed: Cellulose biosynthesis inhibitors: comparative effect on bean cell cultures. PubMed: Gas chromatography/isotope ratio mass spectrometry of recalcitrant target compounds: performance of different combustion reactors and strategies for standardization. PubMed: C and N isotope fractionation during biodegradation of the pesticide metabolite 2,6-dichlorobenzamide (BAM): potential for environmental assessments. PubMed: Simultaneous analysis of pesticides from different chemical classes by using a derivatisation step and gas chromatography-mass spectrometry. PubMed: Dichlobenil and 2,6-dichlorobenzamide (BAM) in the environment: what are the risks to humans and biota? PubMed: Inherent mineralization of 2,6-dichlorobenzamide (BAM) in unsaturated zone and aquifers--effect of initial concentrations and adaptation. PubMed: Changes in cinnamic acid derivatives associated with the habituation of maize cells to dichlobenil. PubMed: Before the curtain falls: endocrine-active pesticides--a German contamination legacy. PubMed: Analysis and environmental concentrations of the herbicide dichlobenil and its main metabolite 2,6-dichlorobenzamide (BAM): a review. PubMed: Adsorption of diuron and dichlobenil on multiwalled carbon nanotubes as affected by lead. PubMed: Deepening into the proteome of maize cells habituated to the cellulose biosynthesis inhibitor dichlobenil. PubMed: Habituation to thaxtomin A in hybrid poplar cell suspensions provides enhanced and durable resistance to inhibitors of cellulose synthesis. PubMed: The phenolic profile of maize primary cell wall changes in cellulose-deficient cell cultures. PubMed: Unraveling the biochemical and molecular networks involved in maize cell habituation to the cellulose biosynthesis inhibitor dichlobenil. PubMed: Plasticity of xyloglucan composition in bean (Phaseolus vulgaris)-cultured cells during habituation and dehabituation to lethal concentrations of dichlobenil. PubMed: Callose implication in stomatal opening and closure in the fern Asplenium nidus. PubMed: Hydrolysis of benzonitrile herbicides by soil actinobacteria and metabolite toxicity. PubMed: Development of a multiresidue method for the determination of multiclass pesticides in soil using GC. PubMed: Permeation of herbicidal dichlobenil from a Casoron formulation through nitrile gloves. PubMed: Habituation and dehabituation to dichlobenil: simply the equivalent of Penélope's weaving and unweaving process? PubMed: The role of callose in guard-cell wall differentiation and stomatal pore formation in the fern Asplenium nidus. PubMed: Competitive biodegradation of dichlobenil and atrazine coexisting in soil amended with a char and citrate. PubMed: Toxicological study of pesticides in air and precipitations of Paris by means of a bioluminescence method. PubMed: Microtubule involvement in the deposition of radial fibrillar callose arrays in stomata of the fern Asplenium nidus L. PubMed: Human cord blood CD133+ stem cells transplanted to nod-scid mice provide conditions for regeneration of olfactory neuroepithelium after permanent damage induced by dichlobenil. PubMed: High peroxidase activity and stable changes in the cell wall are related to dichlobenil tolerance. PubMed: The most-probable-number enumeration of dichlobenil and 2,6-dichlorobenzamide (BAM) degrading microbes in Finnish aquifers. PubMed: A methodology to determine pesticides pollution sources in water catchments: study case (Belgium). PubMed: Novel type II cell wall architecture in dichlobenil-habituated maize calluses. PubMed: GC-MS analysis of dichlobenil and its metabolites in groundwater. PubMed: Sorption of polar and nonpolar aromatic compounds to four surface soils of eastern China. PubMed: Sorption of aromatic compounds to clay mineral and model humic substance-clay complex: effects of solute structure and exchangeable cation. PubMed: Habituation of bean (Phaseolus vulgaris) cell cultures to Quinclorac and analysis of the subsequent cell wall modifications. PubMed: Microbial degradation of the benzonitrile herbicides dichlobenil, bromoxynil and ioxynil in soil and subsurface environments--insights into degradation pathways, persistent metabolites and involved degrader organisms. PubMed: [Toward a better knowledge of the pesticides used by municipality in rural society: example of Limousin Region (France)]. PubMed: Increase in XET activity in bean (Phaseolus vulgaris L.) cells habituated to dichlobenil. PubMed: Microbial degradation pathways of the herbicide dichlobenil in soils with different history of dichlobenil-exposure. PubMed: Demonstrating formation of potentially persistent transformation products from the herbicides bromoxynil and ioxynil using liquid chromatography-tandem mass spectrometry (LC-MS/MS). PubMed: Degradation of the herbicide dichlobenil and its metabolite BAM in soils and subsurface sediments. PubMed: Degradation and mineralization of nanomolar concentrations of the herbicide dichlobenil and its persistent metabolite 2,6-dichlorobenzamide by Aminobacter spp. isolated from dichlobenil-treated soils. PubMed: Mineralisation of 2,6-dichlorobenzamide (BAM) in dichlobenil-exposed soils and isolation of a BAM-mineralising Aminobacter sp. PubMed: Transformation of the herbicide 2,6-dichlorobenzonitrile to the persistent metabolite 2,6-dichlorobenzamide (BAM) by soil bacteria known to harbour nitrile hydratase or nitrilase. PubMed: CYP2A5-mediated activation and early ultrastructural changes in the olfactory mucosa: studies on 2,6-dichlorophenyl methylsulfone. PubMed: Identification and quantification of pesticides, industrial chemicals, and organobromine compounds of medium to high polarity in the North Sea. PubMed: Geochemical modulation of pesticide sorption on smectite clay. PubMed: Olfactory mucosal toxicity screening and multivariate QSAR modeling for chlorinated benzene derivatives. PubMed: Sorption of the herbicide dichlobenil and the metabolite 2,6-dichlorobenzamide on soils and aquifer sediments. PubMed: Zonal ablation of the olfactory sensory neuroepithelium of the mouse: effects on odorant detection. PubMed: Effects of beta-naphthoflavone, phenobarbital and dichlobenil on the drug-metabolizing system of liver and nasal mucosa of Italian water frogs. PubMed: Quantitative microarray pesticide analysis. PubMed: Axon mis-targeting in the olfactory bulb during regeneration of olfactory neuroepithelium. PubMed: Quantitative assessment of factors affecting the sensitivity of a competitive immunomicroarray for pesticide detection. PubMed: Cell-specific expression of CYP2A5 in the mouse respiratory tract: effects of olfactory toxicants. PubMed: Differential effects of olfactory toxicants on olfactory regeneration. PubMed: Laminar disorganisation of mitral cells in the olfactory bulb does not affect topographic targeting of primary olfactory axons. PubMed: Cell wall modifications of bean (Phaseolus vulgaris) cell suspensions during habituation and dehabituation to dichlobenil. PubMed: Ultrastructural effects of cellulose biosynthesis inhibitor herbicides on developing cotton fibers. PubMed: Degradation of herbicides in shallow Danish aquifers: an integrated laboratory and field study. PubMed: Potential contributions of smectite clays and organic matter to pesticide retention in soils. PubMed: Herbicidal properties of the thaxtomin group of phytotoxins. PubMed: Characterization of cell walls in bean (Phaseolus vulgaris L.) callus cultures tolerant to dichlobenil. PubMed: A quantitative enzyme-linked immunoassay for the detection of 2, 6-dichlorobenzamide (BAM), a degradation product of the herbicide dichlobenil. PubMed: Estimation of dioxin emission from fires in chemicals. PubMed: Degeneration and gliosis in rat retina and central nervous system following 3,3'-iminodipropionitrile exposure. PubMed: Abiotic degradation of halobenzonitriles: investigation of the photolysis in solution. PubMed: A cytokinesis-defective mutant of Arabidopsis (cyt1) characterized by embryonic lethality, incomplete cell walls, and excessive callose accumulation. PubMed: Metabolism-dependent activation and toxicity of chemicals in nasal glands. PubMed: Cell- and tissue-specific metabolic activation of chemicals as determined by autoradiography: in vitro-in vivo correlations. PubMed: Effects of dichlobenil on ultrastructural morphology and cell replication in the mouse olfactory mucosa. PubMed: G-protein(S), G alpha q/G alpha 11, in the olfactory neuroepithelium of the channel catfish (Ictalurus punctatus) is altered by the herbicide, dichlobenil. PubMed: High-performance liquid chromatographic study of the aromatic nitrile metabolism in soil bacteria. PubMed: 3-Aminobenzamide: effects on cytochrome P450-dependent metabolism of chemicals and on the toxicity of dichlobenil in the olfactory mucosa. PubMed: Characterization of olfactory deficits in the rat following administration of 2,6-dichlorobenzonitrile (dichlobenil), 3,3'-iminodipropionitrile, or methimazole. PubMed: Physiological and histological recovery of the olfactory mucosa of the frog after a dichlobenil injection. PubMed: Distribution of microsomal epoxide hydrolase and glutathione S-transferase in the rat olfactory mucosa: relevance to distribution of lesions caused by systemically-administered olfactory toxicants. PubMed: Olfactory toxicity of diethyldithiocarbamate (DDTC) and disulfiram and the protective effect of DDTC against the olfactory toxicity of dichlobenil. PubMed: Metabolic activation of the olfactory toxicant, dichlobenil, in rat olfactory microsomes: comparative studies with p-nitrophenol. PubMed: Dichlobenil in the fetal and neonatal mouse olfactory mucosa. PubMed: Taurine in the olfactory system: effects of the olfactory toxicant dichlobenil. PubMed: Olfactory toxicity resulting from dermal application of 2,6-dichlorobenzonitrile (dichlobenil) in the C57Bl mouse. PubMed: Olfactory cytochrome P-450 immunoreactivity in mice is altered by dichlobenil but preserved by metyrapone. PubMed: Pesticides in rainfall and air in Italy. PubMed: Tissue-binding and toxicity of compounds structurally related to the herbicide dichlobenil in the mouse olfactory mucosa. PubMed: Effects of glutathione-modulating agents on the covalent binding and toxicity of dichlobenil in the mouse olfactory mucosa. PubMed: Simultaneous separation and determination of hydrocarbons and organochlorine compounds by using a two-step microcolumn. PubMed: Toxicity of 2,6-dichlorothiobenzamide (chlorthiamid) and 2,6-dichlorobenzamide in the olfactory nasal mucosa of mice. PubMed: A one-year carcinogenicity study with 2,6-dichlorobenzonitrile (Dichlobenil) in male Swiss mice: preliminary note. PubMed: Metabolic activation of the herbicide dichlobenil in the olfactory mucosa of mice and rats. PubMed: Isoxaben Inhibits the Synthesis of Acid Insoluble Cell Wall Materials In Arabidopsis thaliana. PubMed: Irreversible binding and toxicity of the herbicide dichlobenil (2,6-dichlorobenzonitrile) in the olfactory mucosa of mice. PubMed: Intermediary metabolism of 2,6-dichlorobenzonitrile (dichlobenil) in chickens and growth of chickens fed dichlobenil. PubMed: The influence of two culturing techniques on toxicity of four chemicals in Arabidopsis. PubMed: Time Course of Induction of Cytochrome P-450, NADPH-Cytochrome c Reductase, and Cinnamic Acid Hydroxylase by Phenobarbital, Ethanol, Herbicides, and Manganese in Higher Plant Microsomes. PubMed: Metabolism of dichlobenil by microorganisms in the aquatic environment. PubMed: A multi-residue extraction procedure for the gas chromatographic determination of the herbicides dichlobenil, dinitramine, triallate and trifluralin in soils. PubMed: Persistence of dichlobenil in a farm pond. PubMed: Uptake and metabolsim of dichlobenil by emersed aquatic plants. PubMed: Residues in ponds treated with two formulations of dichlobenil. PubMed: Uptake and effects of dichlobenil in a small pond. PubMed: A side effect of chlorthiamid and dichlobenil herbicides. PubMed: Toxicology of the herbicide dichlobenil (2,6-dichlorobenzonitrile) and its main metabolites. PubMed: Considerations of the vapor pressure of dichlobenil affecting its use and procedure for residue analysis.