bromoxynil
4-hydroxy-3,5-dibromobenzonitrile
 
Notes:
None found
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CAS Number: 1689-84-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 216-882-7
FDA UNII: J46EK95K0P
Nikkaji Web: J7.557D
Beilstein Number: 2364039
MDL: MFCD00002153
XlogP3-AA: 3.50 (est)
Molecular Weight: 276.91511000
Formula: C7 H3 Br2 N O
NMR Predictor: Predict (works with chrome or firefox)
Category: herbicides / pesticides
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Appearance: colorless solid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 190.00 °C. @ 760.00 mm Hg
Soluble in:
 water, 130 mg/L @ 25 °C (exp)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
Bromoxynil
Sigma-Aldrich
For experimental / research use only.
Bromoxynil PESTANAL®, analytical standard
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-bird - wild LD50  50 mg/kg
Pesticide Manual. Vol. 9, Pg. 100, 1991.

oral-chicken LD50  240 mg/kg
Pesticide Manual. Vol. 9, Pg. 100, 1991.

oral-dog LD50  100 mg/kg
"Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A045, Pg. 1983

oral-duck LD50  200 mg/kg
Down to Earth. Vol. 35, Pg. 25, 1979.

oral-guinea pig LD50  63 mg/kg
Guide to the Chemicals Used in Crop Protection. Vol. 6, Pg. 55, 1973.

unreported-mammal (species unspecified) LD50  190 mg/kg
"Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 150, 1971.

intravenous-mouse LD50  56 mg/kg
U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02212

oral-mouse LD50  110 mg/kg
Guide to the Chemicals Used in Crop Protection. Vol. 6, Pg. 55, 1973.

oral-rabbit LD50  260 mg/kg
"Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976.

oral-rat LD50  190 mg/kg
World Review of Pest Control. Vol. 9, Pg. 119, 1970.

Dermal Toxicity:
skin-rabbit LD50 3660 mg/kg
Pesticide Manual. Vol. 9, Pg. 100, 1991.

skin-rat LD50 > 2 mg/kg
Pesticide Manual. Vol. 9, Pg. 100, 1991.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: herbicides / pesticides
Recommendation for bromoxynil usage levels up to:
 not for fragrance use.
 
Recommendation for bromoxynil flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Modification of the existing maximum residue level (MRL) for bromoxynil in chives
View page or View pdf
Protocol for the evaluation of data concerning the necessity of the application of herbicide active substances to control a serious danger to plant health which cannot be contained by other available means, including non-chemical methods
View page or View pdf
Peer review of the pesticide risk assessment of the active substance bromoxynil (variant evaluated bromoxynil octanoate)
View page or View pdf
Evaluation of data concerning the necessity of bromoxynil as herbicide to control a serious danger to plant health which cannot be contained by other available means, including non-chemical methods
View page or View pdf
Peer review of the pesticide risk assessment for the active substance bromoxynil in light of negligible exposure data submitted
View page or View pdf
EPI System: View
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 15531
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 3,5-dibromo-4-hydroxybenzonitrile
Chemidplus: 0001689845
EPA/NOAA CAMEO: hazardous materials
RTECS: DI3150000 for cas# 1689-84-5
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References:
 3,5-dibromo-4-hydroxybenzonitrile
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 15531
Pubchem (sid): 134979047
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
UM BBD: Search
KEGG (GenomeNet): C04178
HMDB (The Human Metabolome Database): Search
Export Tariff Code: 2926.90.2300
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
 benzonitrile, 3,5-dibromo-4-hydroxy-
 brittox
 brominal
 brominal plus
 brominal triple
 brominex
 brominil
 bromotril
 bromoxynil phenol
 buctril
 butil chlorofos
 butilchorofos
 certrol B
 chipco buctril
 chipco crab-kleen
4-cyano-2,6-dibromophenol
2,6-dibromo-4-cyanophenol
3,5-dibromo-4-hydroxybenzonitril (ACN)
3,5-dibromo-4-hydroxybenzonitrile
3,5-dibromo-4-hydroxyphenyl cyanide
3,5-dibromo-4-hydroxyphenylcyanide
4-hydroxy-3,5-dibromobenzonitrile
 labuctril 25
 litarol M
 M&B 10731
 novacorn
 oxytril M
 pardner
 sabre
 terset
 toplan
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Articles:
PubMed: 2-Methyl-4-chlorophenoxyacetic acid and bromoxynil herbicide death.
PubMed: Synthesis and evaluation of heterocyclic analogues of bromoxynil.
PubMed: An essential esterase (BroH) for the mineralization of bromoxynil octanoate by a natural consortium of Sphingopyxis sp. strain OB-3 and Comamonas sp. strain 7D-2.
PubMed: [Induction cell damage and change of nuclear factor-kappa B expression by bromoxynil in SH-SY5Y cells].
PubMed: A bentazone-resistant mutant of cyanobacterium, Synechococcus elongatus PCC7942 adapts different strategies to counteract on bromoxynil- and salt-mediated oxidative stress.
PubMed: Photodegradation routes of the herbicide bromoxynil in solution and sorbed on silica nanoparticles.
PubMed: Further electrophysiological studies on cellular effect of herbicide, bromoxynil, using characean cells.
PubMed: Use of a potentiometric vital dye to determine the effect of the herbicide bromoxynil octanoate on mitochondrial bioenenergetics in Chlamydomonas reinhardtii.
PubMed: Bromoxynil residues and dissipation rates in maize crops and soil.
PubMed: Degradation of bromoxynil octanoate by strain Acinetobacter sp. XB2 isolated from contaminated soil.
PubMed: [Intervention effect of dimercaptopropansulfonate sodium on central toxic induced by bromoxynil in vivo].
PubMed: Unique cellular effect of the herbicide bromoxynil revealed by electrophysiological studies using characean cells.
PubMed: Degradation of three benzonitrile herbicides by Aminobacter MSH1 versus soil microbial communities: pathways and kinetics.
PubMed: Molecular mechanisms of herbicide-inducible gene expression of tobacco CYP71AH11 metabolizing the herbicide chlorotoluron.
PubMed: Degradation of bromoxynil and trifluralin in natural water by direct photolysis and UV plus H(2)O(2) advanced oxidation process.
PubMed: Photosensitized degradation in water of the phenolic pesticides bromoxynil and dichlorophen in the presence of riboflavin, as a model of their natural photodecomposition in the environment.
PubMed: [Effect of bromoxynil on membrane potential and respiratory control rate in isolated mitochondria from mice liver and intervention effect of NAC].
PubMed: Bromoxynil degradation in a Mississippi silt loam soil.
PubMed: Determination of bromoxynil octanoate in soil and corn by GC with electron capture and mass spectrometry detection under field conditions.
PubMed: Primary effect of bromoxynil to induce plant cell death may be cytosol acidification.
PubMed: The application of the herbicide bromoxynil to a model soil-derived bacterial community: impact on degradation and community structure.
PubMed: Dehalogenation of the herbicides bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) and ioxynil (3,5-diiodino-4-hydroxybenzonitrile) by Desulfitobacterium chlororespirans.
PubMed: Exposure of ground-rig applicators to the herbicide bromoxynil applied as a 1:1 mixture of butyrate and octanoate.
PubMed: The degradation of the herbicide bromoxynil and its impact on bacterial diversity in a top soil.
PubMed: Body mass index and bromoxynil exposure in a sample of rural residents during spring herbicide application.
PubMed: Factors associated with detection of bromoxynil in a sample of rural residents.
PubMed: Biodegradation of the herbicide bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) by purified pentachlorophenol hydroxylase and whole cells of Flavobacterium sp. strain ATCC 39723 is accompanied by cyanogenesis.
PubMed: Developmental toxicity of bromoxynil in mice and rats.
PubMed: Antinuclear antibodies and bromoxynil exposure in a rural sample.
PubMed: Metabolism of the herbicide bromoxynil by Klebsiella pneumoniae subsp. ozaenae.
PubMed: Short- and long-term response of sunflower to airborne bromoxynil-octanoate under controlled and field conditions.
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 ioxynil and bromoxynil as measured by a modified spectrophotometric method.
PubMed: Enzymic degradation of bromoxynil by cell-free extracts of Streptomyces felleus.
PubMed: Cloning and expression in Escherichia coli of a Klebsiella ozaenae plasmid-borne gene encoding a nitrilase specific for the herbicide bromoxynil.
PubMed: Development of an immunochromatographic assay for the rapid detection of bromoxynil in water.
PubMed: Flow injection spectrophotometric determination of bromoxynil herbicide by diazotization method.
PubMed: Development of an ELISA for the detection of bromoxynil in water.
PubMed: Purification and properties of a nitrilase specific for the herbicide bromoxynil and corresponding nucleotide sequence analysis of the bxn gene.
PubMed: Probing the quinone binding site of photosystem II from Thermosynechococcus elongatus containing either PsbA1 or PsbA3 as the D1 protein through the binding characteristics of herbicides.
PubMed: Effects of 3,5-Dibromo-4-Hydroxybenzonitrile (Bromoxynil) on Bioenergetics of Higher Plant Mitochondria (Pisum sativum).
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: Substrate selectivity and conformational space available to bromoxynil and acrylonitrile in iron nitrile hydratase.
PubMed: Bacterial degradation of the herbicide bromoxynil by Agrobacterium radiobacter in biofilm.
PubMed: Degradation of the herbicide bromoxynil in Pseudomonas putida.
PubMed: HPLC measurement of chlorophenoxy herbicides, bromoxynil, and ioxynil, in biological specimens to aid diagnosis of acute poisoning.
PubMed: Impact of an herbicide combination of bromoxynil and prosulfuron on soil microorganisms.
PubMed: Chemiluminescent determination of the pesticide bromoxynil by on-line photodegradation in a flow-injection system.
PubMed: Semi-permeable surface analytical reversed-phase column for the improved trace analysis of acidic pesticides in water with coupled-column reversed-phase liquid chromatography with UV detection. Determination of bromoxynil and bentazone in surface water.
PubMed: Effect of airborne bromoxynil-octanoate and metribuzin on non-target plants.
PubMed: Molecular characterization of the enzymes involved in the degradation of a brominated aromatic herbicide.
PubMed: Axial skeletal and Hox expression domain alterations induced by retinoic acid, valproic acid, and bromoxynil during murine development.
PubMed: Effect of glucose and ribose on microbial degradation of the herbicide bromoxynil continuously added to soil.
PubMed: [Results of the toxicokinetics of bromoxynil in rats].
PubMed: Environmental concentrations of agricultural herbicides in Saskatchewan, Canada: bromoxynil, dicamba, diclofop, MCPA, and trifluralin.
PubMed: [First aid and nursing on acute severe bromoxynil poisoning].
PubMed: EPA ban on bromoxynil undercuts Calgene's transgenic cotton.
PubMed: [Experimental study on toxicity and changes of biochemical indicator in acute bromoxynil poisoning].
PubMed: [Study on clinical treatment of acute bromoxynil poisoning].
PubMed: [Investigation on an accident of death induced by bromoxynil poisoning].
PubMed: Simultaneous extraction and detection of residues of (2,4-dichlorophenoxy)acetic acid and bromoxynil from wheat.
PubMed: Biotransformation of benzonitrile herbicides via the nitrile hydratase-amidase pathway in rhodococci.
PubMed: Analysis of airborne pesticides from different chemical classes adsorbed on Radiello® Tenax® passive tubes by thermal-desorption-GC/MS.
PubMed: Study of Cytotoxic Effects of Benzonitrile Pesticides.
PubMed: Comparison of liquid and gas chromatography for the determination of bromoxynil octanoate and benzoylprop ethyl in wheat products.
PubMed: The in vitro degradation of the herbicide bromoxynil.
PubMed: Fate of the herbicides bromoxynil and casoron in cows.
PubMed: Kinetics and mechanism of the degradation of two pesticides in aqueous solutions by ozonation.
PubMed: Hydrolysis of benzonitrile herbicides by soil actinobacteria and metabolite toxicity.
PubMed: Dissipation of six acid herbicides in water and sediment of two Canadian prairie wetlands.
PubMed: Metabolism of agrochemicals and related environmental chemicals based on cytochrome P450s in mammals and plants.
PubMed: Biotransformation of 3,5-dibromo-4-hydroxybenzonitrile under denitrifying, Fe(III)-reducing, sulfidogenic, and methanogenic conditions.
PubMed: Exposure to herbicides in house dust and risk of childhood acute lymphoblastic leukemia.
PubMed: Effects of a herbicide mixture on primary and bacterial productivity in four prairie wetlands with varying salinities: an enclosure approach.
PubMed: Enchytraeidae Fridericia bulbosa as a new test species for soil ecotoxicity assessment.
PubMed: Oxidation kinetics of two pesticides in natural waters by ozonation and ozone combined with hydrogen peroxide.
PubMed: Determination and occurrence of phenoxyacetic acid herbicides and their transformation products in groundwater using ultra high performance liquid chromatography coupled to tandem mass spectrometry.
PubMed: Long-range interaction between the Mn4CaO5 cluster and the non-heme iron center in photosystem II as revealed by FTIR spectroelectrochemistry.
PubMed: Structures and binding sites of phenolic herbicides in the Q(B) pocket of photosystem II.
PubMed: Residential agricultural pesticide exposures and risk of neural tube defects and orofacial clefts among offspring in the San Joaquin Valley of California.
PubMed: How does the QB site influence propagate to the QA site in photosystem II?
PubMed: Pleiotropic effects of herbicide-resistance genes on crop yield: a review.
PubMed: A comparative study of nitrilases identified by genome mining.
PubMed: Autodisplay of nitrilase from Klebsiella pneumoniae and whole-cell degradation of oxynil herbicides and related compounds.
PubMed: Herbicide effect on the photodamage process of photosystem II: fourier transform infrared study.
PubMed: Energetics in photosystem II from Thermosynechococcus elongatus with a D1 protein encoded by either the psbA1 or psbA3 gene.
PubMed: Effects of herbicide mixture on microbial communities in prairie wetland ecosystems: a whole wetland approach.
PubMed: Herbicide-induced changes in charge recombination and redox potential of Q(A) in the T4 mutant of Blastochloris viridis.
PubMed: pH-dependence of pesticide adsorption by wheat-residue-derived black carbon.
PubMed: Halogenated pesticide transformation by a laccase-mediator system.
PubMed: Effects of glyphosate and two herbicide mixtures on microbial communities in prairie wetland ecosystems: a mesocosm approach.
PubMed: Occurrence of glyphosate and acidic herbicides in select urban rivers and streams in Canada, 2007.
PubMed: Simultaneous analysis of pesticides from different chemical classes by using a derivatisation step and gas chromatography-mass spectrometry.
PubMed: Abiotic degradation of halobenzonitriles: investigation of the photolysis in solution.
PubMed: Significance of supernumerary ribs in rodent developmental toxicity studies: postnatal persistence in rats and mice.
PubMed: Recovery of non-target plants affected by airborne herbicides.
PubMed: The impact of altered herbicide residues in transgenic herbicide-resistant crops on standard setting for herbicide residues.
PubMed: Effects on aquatic and human health due to large scale bioenergy crop expansion.
PubMed: Herbicide effect on the hydrogen-bonding interaction of the primary quinone electron acceptor QA in photosystem II as studied by Fourier transform infrared spectroscopy.
PubMed: Herbicide resistance in transgenic plants expressing a bacterial detoxification gene.
PubMed: Comparing effects of low levels of herbicides on greenhouse- and field-grown potatoes (Solanum tuberosum L.), soybeans (Glycine max L.), and peas (Pisum sativum L.).
PubMed: Protection by isoprene against singlet oxygen in leaves.
PubMed: OH radical reactivity of pesticides adsorbed on aerosol materials: first results of experiments with filter samples.
PubMed: Atmospheric concentrations and dry and wet deposits of some herbicides currently used on the Canadian Prairies.
PubMed: Herbicidal treatments for control of Papaver somniferum L.
PubMed: Influence of pH on pesticide sorption by soil containing wheat residue-derived char.
PubMed: Interactions of halogenated industrial chemicals with transthyretin and effects on thyroid hormone levels in vivo.
PubMed: Analysis of trace levels of pesticides in rainwater by SPME and GC-tandem mass spectrometry after derivatisation with PFBBr.
PubMed: Importance of surface diffusivities in pesticide adsorption kinetics onto granular versus powdered activated carbon: experimental determination and modeling.
PubMed: High-performance liquid chromatographic study of the aromatic nitrile metabolism in soil bacteria.
PubMed: Tissue-binding and toxicity of compounds structurally related to the herbicide dichlobenil in the mouse olfactory mucosa.
PubMed: Liquid chromatography with post-column reagent addition of ammonia in methanol coupled to negative ion electrospray ionization tandem mass spectrometry for determination of phenoxyacid herbicides and their degradation products in surface water.
PubMed: Imaging plant cell death: GFP-Nit1 aggregation marks an early step of wound and herbicide induced cell death.
PubMed: Crosstalk and differential response to abiotic and biotic stressors reflected at the transcriptional level of effector genes from secondary metabolism.
PubMed: Spatially resolved quantification of agrochemicals on plant surfaces using energy dispersive X-ray microanalysis.
PubMed: Utility of delayed fluorescence as endpoint for rapid estimation of effect concentration on the green alga Pseudokirchneriella subcapitata.
PubMed: psbA mutation (Asn266 to Thr) in Senecio vulgaris L. confers resistance to several PS II-inhibiting herbicides.
PubMed: Diffuse geographic distribution of herbicides in northern prairie wetlands.
PubMed: Mode of action of photosynthesis inhibiting 4-hydroxy-benzonitriles containing nitro group.
PubMed: Carboxylesterase activities toward pesticide esters in crops and weeds.
PubMed: A psbA mutation in Kochia scoparia (L) Schrad from railroad rights-of-way with resistance to diuron, tebuthiuron and metribuzin.
PubMed: Comparative sensitivity of Selenastrum capricornutum and Lemna minor to sixteen herbicides.
PubMed: Herbicide levels in rivers draining two prairie agricultural watersheds (1984).
PubMed: Reactive oxygen species in programmed death of pea guard cells.
PubMed: Chemical weed management in wheat at higher altitudes.
PubMed: [Determination of six pesticides in milk using cloud point extraction-high performance liquid chromatography].
PubMed: Pesticides in surface drinking-water supplies of the northern Great Plains.
PubMed: Autism: transient in utero hypothyroxinemia related to maternal flavonoid ingestion during pregnancy and to other environmental antithyroid agents.
PubMed: Virtual imprinting as a tool to design efficient MIPs for photosynthesis-inhibiting herbicides.
PubMed: A multiresidue method using ion-trap gas chromatography-tandem mass spectrometry with or without derivatisation with pentafluorobenzylbromide for the analysis of pesticides in the atmosphere.
PubMed: Toxicity of a complex mixture of atmospherically transported pesticides to Ceriodaphnia dubia.
PubMed: Comparative efficacy of five herbicides on winter cereal weeds in semi-arid region of Algeria.
PubMed: Discrimination and taxonomy of geographically diverse strains of nitrile-metabolizing actinomycetes using chemometric and molecular sequencing techniques.
PubMed: Microwave assisted solvent extraction and coupled-column reversed-phase liquid chromatography with UV detection use of an analytical restricted-access-medium column for the efficient multi-residue analysis of acidic pesticides in soils.
PubMed: Herbicide and nutrient transport from an irrigation district into the South Saskatchewan River.
PubMed: Suspected herbicide toxicosis in a dog.
PubMed: Nitrilase from Rhodococcus rhodochrous J1. Sequencing and overexpression of the gene and identification of an essential cysteine residue.
PubMed: Cloning and expression of an Arabidopsis nitrilase which can convert indole-3-acetonitrile to the plant hormone, indole-3-acetic acid.
PubMed: Responses of marine unicellular algae to brominated organic compounds in six growth media.
PubMed: Effects of low concentrations of herbicides on full-season, field-grown potatoes.
PubMed: Radiative and non-radiative charge recombination pathways in Photosystem II studied by thermoluminescence and chlorophyll fluorescence in the cyanobacterium Synechocystis 6803.
PubMed: Quality control of photosystem II. Cleavage of reaction center D1 protein in spinach thylakoids by FtsH protease under moderate heat stress.
PubMed: Spatial and geographical variations of urban, suburban and rural atmospheric concentrations of phenols and nitrophenols.
PubMed: Taking stock of herbicide-resistant crops ten years after introduction.
PubMed: Acceptor and donor-side interactions of phenolic inhibitors in Photosystem II.
PubMed: Singlet oxygen production in herbicide-treated photosystem II.
PubMed: Study of matrix effects on the direct trace analysis of acidic pesticides in water using various liquid chromatographic modes coupled to tandem mass spectrometric detection.
PubMed: Analysis of acidic pesticides using in situ derivatization with alkylchloroformate and solid-phase microextraction (SPME) for GC-MS.
PubMed: Modelling agrochemical dissipation in surface microlayers following aerial deposition
PubMed: Primary structure of an aliphatic nitrile-degrading enzyme, aliphatic nitrilase, from Rhodococcus rhodochrous K22 and expression of its gene and identification of its active site residue.
PubMed: Synthesis of aryl D-gluco- and D-galacto-pyranosides and 1-O-acyl-D-gluco- and -D-galacto-pyranoses exploiting the Mitsunobu reaction. Influence of the pKa of the acid on the stereoselectivity of the reaction.
PubMed: Evaluation of polyurethane foam as a trapping medium for herbicide vapor in air monitoring and worker inhalation studies.
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