diclofop
methyl 2-(4-(2,4-dichlorophenyoxy)phenoxy)propanoate
 
Notes:
None found
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CAS Number: 40843-25-2Picture of molecule3D/inchi
Other(deleted CASRN): 75045-49-7
FDA UNII: 3LN56779KT
Nikkaji Web: J20.671G
Beilstein Number: 2338390
MDL: MFCD00152216
XlogP3-AA: 5.00 (est)
Molecular Weight: 327.16144000
Formula: C15 H12 Cl2 O4
NMR Predictor: Predict (works with chrome or firefox)
Category: herbicides / pesticides
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 120.00 °C. @ 760.00 mm Hg
logP (o/w): 4.580
Soluble in:
 water, 453 mg/L @ 20 °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:
Sigma-Aldrich
For experimental / research use only.
(±)-Diclofop
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Safety Information:
 
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-quail LD50  > 10000 mg/kg
Pesticide Manual. Vol. 9, Pg. 262, 1991.

oral-rat LD50  563 mg/kg
Pesticide Manual. Vol. 9, Pg. 262, 1991.

Dermal Toxicity:
skin-rat LD50 > 5000 mg/kg
Pesticide Manual. Vol. 9, Pg. 262, 1991.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: herbicides / pesticides
Recommendation for diclofop usage levels up to:
 not for fragrance use.
 
Recommendation for diclofop flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Outcome of the consultation with Member States, the applicant and EFSA on the pesticide risk assessment for diclofop (considered variant diclofop-methyl) in light of confirmatory data
View page or View pdf
Review of the existing maximum residue levels for diclofop (considered variant diclofop-methyl) according to Article 12 of Regulation (EC) No 396/2005
View page or View pdf
EPI System: View
AIDS Citations: Search
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 38687
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid
Chemidplus: 0040843252
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References:
 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 38687
Pubchem (sid): 135000973
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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
KEGG (GenomeNet): C18716
HMDB (The Human Metabolome Database): Search
ChemSpider: View
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:
 dichlorfop acid
2-(4-(2,4-dichlorophenoxy)phenoxy)propanoic acid
(RS)-2-(4-(2,4-dichlorophenoxy)phenoxy)propionic acid
2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid
 methyl (RS)-2-(4-(2,4-dichlorophenoxy)phenoxy)propionate
 methyl 2-(4-(2,4-dichlorophenyoxy)phenoxy)propanoate
 propanoic acid, 2-(4-(2,4-dichlorophenoxy)phenoxy)-
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Articles:
PubMed: Stereoselective Behavior of the Chiral Herbicides Diclofop-Methyl and Diclofop During the Soy Sauce Brewing Process.
PubMed: Ile-1781-Leu and Asp-2078-Gly Mutations in ACCase Gene, Endow Cross-resistance to APP, CHD, and PPZ in Phalaris minor from Mexico.
PubMed: Evaluation of Ricinus communis L. for the Phytoremediation of Polluted Soil with Organochlorine Pesticides.
PubMed: Isolation of an aryloxyphenoxy propanoate (AOPP) herbicide-degrading strain Rhodococcus ruber JPL-2 and the cloning of a novel carboxylesterase gene (feh).
PubMed: Response to low-dose herbicide selection in self-pollinated Avena fatua.
PubMed: Widespread occurrence of both metabolic and target-site herbicide resistance mechanisms in Lolium rigidum populations.
PubMed: Evolution of herbicide resistance mechanisms in grass weeds.
PubMed: Exposure to difenoconazole, diclofop-methyl alone and combination alters oxidative stress and biochemical parameters in albino rats.
PubMed: Unraveling the toxicity mechanisms of the herbicide diclofop-methyl in rice: modulation of the activity of key enzymes involved in citrate metabolism and induction of cell membrane anion channels.
PubMed: Enantioselective metabolism of the chiral herbicide diclofop-methyl and diclofop by HPLC in loach (Misgurnus anguillicaudatus) liver microsomes in vitro.
PubMed: Modeling the coverage of an AFM tip by enzymes and its application in nanobiosensors.
PubMed: RNA-Seq transcriptome analysis to identify genes involved in metabolism-based diclofop resistance in Lolium rigidum.
PubMed: Enantioselective changes in oxidative stress and toxin release in Microcystis aeruginosa exposed to chiral herbicide diclofop acid.
PubMed: The secretion of organic acids is also regulated by factors other than aluminum.
PubMed: Study of the enantioselective interaction of diclofop and human serum albumin by spectroscopic and molecular modeling approaches in vitro.
PubMed: Evolved polygenic herbicide resistance in Lolium rigidum by low-dose herbicide selection within standing genetic variation.
PubMed: Enhanced herbicide metabolism induced by 2,4-D in herbicide susceptible Lolium rigidum provides protection against diclofop-methyl.
PubMed: Enantioselective physiological effects of the herbicide diclofop on cyanobacterium Microcystis aeruginosa.
PubMed: Mutualism effectiveness and vertical transmission of symbiotic fungal endophytes in response to host genetic background.
PubMed: Enhanced rates of herbicide metabolism in low herbicide-dose selected resistant Lolium rigidum.
PubMed: Enantioselective damage of diclofop acid mediated by oxidative stress and acetyl-CoA carboxylase in nontarget plant Arabidopsis thaliana.
PubMed: Broad resistance to ACCase inhibiting herbicides in a ryegrass population is due only to a cysteine to arginine mutation in the target enzyme.
PubMed: Analysis of enantioselective biochemical, physiological, and transcriptional effects of the chiral herbicide diclofop methyl on rice seedlings.
PubMed: Enantiomeric resolution of five chiral pesticides on a Chiralpak IB-H column by SFC.
PubMed: A comparative study of drug resistance mechanism associated with active site and non-active site mutations: I388N and D425G mutants of acetyl-coenzyme-A carboxylase.
PubMed: Production of monoclonal antibody to herbicide fenoxaprop-ethyl.
PubMed: Genotoxic effects of chlorophenoxy herbicide diclofop-methyl in mice in vivo and in human lymphocytes in vitro.
PubMed: Degradation of cyhalofop-butyl (CyB) by Pseudomonas azotoformans strain QDZ-1 and cloning of a novel gene encoding CyB-hydrolyzing esterase.
PubMed: Multi-walled carbon nanotubes-dispersive solid-phase extraction combined with nano-liquid chromatography for the analysis of pesticides in water samples.
PubMed: Designing an enzyme-based nanobiosensor using molecular modeling techniques.
PubMed: Stereoselective degradation of Diclofop-methyl during alcohol fermentation process.
PubMed: Chemical control of herbicide-resistant Lolium rigidum Gaud. in north-eastern Spain.
PubMed: Genetic control of a cytochrome P450 metabolism-based herbicide resistance mechanism in Lolium rigidum.
PubMed: An aspartate to glycine change in the carboxyl transferase domain of acetyl CoA carboxylase and non-target-site mechanism(s) confer resistance to ACCase inhibitor herbicides in a Lolium multiflorum population.
PubMed: Computational simulations of structural role of the active-site W374C mutation of acetyl-coenzyme-A carboxylase: multi-drug resistance mechanism.
PubMed: Environmental behavior of the chiral aryloxyphenoxypropionate herbicide diclofop-methyl and diclofop: enantiomerization and enantioselective degradation in soil.
PubMed: Distinct non-target site mechanisms endow resistance to glyphosate, ACCase and ALS-inhibiting herbicides in multiple herbicide-resistant Lolium rigidum.
PubMed: Enantioselective effects of chiral herbicide diclofop acid on rice Xiushui 63 seedlings.
PubMed: Time-dependent degradation and toxicity of diclofop-methyl in algal suspensions : emerging contaminants.
PubMed: TiO(2)/BaTiO(3)-assisted photocatalytic mineralization of diclofop-methyl on UV-light irradiation in the presence of oxidizing agents.
PubMed: One- and two-dimensional direct chiral liquid chromatographic determination of mixtures of diclofop-Acid and diclofop-methyl herbicides.
PubMed: Enantioselective degradation and ecotoxicity of the chiral herbicide diclofop in three freshwater alga cultures.
PubMed: Diversity of acetyl-coenzyme A carboxylase mutations in resistant Lolium populations: evaluation using clethodim.
PubMed: Chlorophyll a fluorescence as a biomarker for rapid toxicity assessment.
PubMed: Malonyl coenzyme A affects insulin-stimulated glucose transport in myotubes.
PubMed: Relation of diclofop-methyl toxicity and degradation in algae cultures.
PubMed: Cross-resistance profile of mesosulfuron-methyl-resistant Italian ryegrass in the southern United States.
PubMed: Chiral separations of pesticide enantiomers by high-performance liquid chromatography using cellulose triphenylcarbamate chiral stationary phase.
PubMed: Superheated water extraction and phase transfer methylation of phenoxy acid herbicides from solid matrices.
PubMed: In vitro screening of 200 pesticides for agonistic activity via mouse peroxisome proliferator-activated receptor (PPAR)alpha and PPARgamma and quantitative analysis of in vivo induction pathway.
PubMed: Agricultural pesticide use and hypospadias in eastern Arkansas.
PubMed: Environmental significance of the diclofop-methyl and cyclodextrin inclusion complexes.
PubMed: Use of tert-butylbenzoylated tartardiamide chiral stationary phase for the enantiomeric resolution of acidic compounds by nano-liquid chromatography.
PubMed: Structural basis for the enantiospecificities of R- and S-specific phenoxypropionate/alpha-ketoglutarate dioxygenases.
PubMed: Enantiomeric resolution of chiral pesticides by high-performance liquid chromatography.
PubMed: Determination of commonly used herbicides in surface water using solid-phase extraction and dual-column HPLC-DAD.
PubMed: High survival frequencies at low herbicide use rates in populations of Lolium rigidum result in rapid evolution of herbicide resistance.
PubMed: Environmental effects of inclusion complexation between methylated beta-cyclodextrin and diclofop-methyl.
PubMed: Pesticide transport in an aerobic aquifer with variable pH--modeling of a field scale injection experiment.
PubMed: Bioluminescence determination of enzyme activity of firefly luciferase in the presence of pesticides.
PubMed: Effects of methyl-CD and humic acid on hydrolytic degradation of the herbicide diclofop-methyl.
PubMed: Lolium rigidum, a pool of resistance mechanisms to ACCase inhibitor herbicides.
PubMed: Cross resistance to accase herbicide in Lolium rigidum.
PubMed: Recurrent selection with reduced herbicide rates results in the rapid evolution of herbicide resistance in Lolium rigidum.
PubMed: Environmental concentrations of agricultural herbicides in Saskatchewan, Canada: bromoxynil, dicamba, diclofop, MCPA, and trifluralin.
PubMed: Herbicide selection of Italian ryegrass under different levels of UVB radiation.
PubMed: Cross-resistance to ACCase inhibitors of Lolium multiflorum, Lolium perenne and Lolium rigidum found in Chile.
PubMed: Molecular basis for the inhibition of the carboxyltransferase domain of acetyl-coenzyme-A carboxylase by haloxyfop and diclofop.
PubMed: Abiotic stress alters transcript profiles and activity of glutathione S-transferase, glutathione peroxidase, and glutathione reductase in Euphorbia esula.
PubMed: Application of solid-phase extraction and micellar electrokinetic capillary chromatography to the study of hydrolytic and photolytic degradation of phenoxy acid and phenylurea herbicides.
PubMed: Tank-mix adjuvants and pesticide residues: some regulatory and quantitative aspects.
PubMed: Determination of herbicides, including thermally labile phenylureas, by solid-phase microextraction and gas chromatography-mass spectrometry.
PubMed: Characterisation of target-site resistance to ACCase-inhibiting herbicides in the weed Alopecurus myosuroides (black-grass).
PubMed: Comparative efficacy of five herbicides on winter cereal weeds in semi-arid region of Algeria.
PubMed: Microscale evaluation of the effects of grazing by invertebrates with contrasting feeding modes on river biofilm architecture and composition.
PubMed: [Effect of diclofop on the activity of some drug-metabolizing enzymes in the liver of male Wistar rats].
PubMed: PCR-based detection of resistance to acetyl-CoA carboxylase-inhibiting herbicides in black-grass (Alopecurus myosuroides Huds) and ryegrass (Lolium rigidum gaud).
PubMed: Effect of cropping cycles and repeated herbicide applications on the degradation of diclofop-methyl, bentazone, diuron, isoproturon and pendimethalin in soil.
PubMed: Induction and inactivation of a cytochrome P450 confering herbicide resistance in wheat seedlings.
PubMed: Sorption and metabolism of selected herbicides in river biofilm communities.
PubMed: Resistance to ACCase-inhibiting herbicides and isoproturon in UK populations of Lolium multiflorum: mechanisms of resistance and implications for control.
PubMed: Degradation of the phenoxy acid herbicide diclofop-methyl by Sphingomonas paucimobilis isolated from a Canadian prairie soil.
PubMed: Studies of early hepatocellular proliferation and peroxisomal proliferation in Wistar rats treated with herbicide diclofop.
PubMed: Molecular analysis and development of 16S rRNA oligonucleotide probes to characterize a diclofop-methyl-degrading biofilm consortium.
PubMed: Two complementary bioassays for screening the estrogenic potency of xenobiotics: recombinant yeast for trout estrogen receptor and trout hepatocyte cultures.
PubMed: Biomimetic oxidation of plant protecting agents.
PubMed: Degradation of diclofop-methyl by pure cultures of bacteria isolated from Manitoban soils.
PubMed: Isolation and characterization of soil microorganisms capable of utilizing the herbicide diclofop-methyl as a sole source of carbon and energy.
PubMed: Tandem mass spectrometry of herbicide residues in lipid-rich tissue.
PubMed: Bioaccumulation of the Herbicide Diclofop in Extracellular Polymers and Its Utilization by a Biofilm Community during Starvation.
PubMed: Purification and Characterization of Acetyl-Coenzyme A Carboxylase from Diclofop-Resistant and -Susceptible Lolium multiflorum.
PubMed: Localization and characterization of two structurally different forms of acetyl-CoA carboxylase in young pea leaves, of which one is sensitive to aryloxyphenoxypropionate herbicides.
PubMed: Microbial exopolymers provide a mechanism for bioaccumulation of contaminants.
PubMed: The role of interactions, sessile growth and nutrient amendments on the degradative efficiency of a microbial consortium.
PubMed: Multicellular organization in a degradative biofilm community.
PubMed: Effects of Acetyl-Coenzyme A Carboxylase Inhibitors on Root Cell Transmembrane Electric Potentials in Graminicide-Tolerant and -Susceptible Corn (Zea mays L.).
PubMed: Development of steady-state diffusion gradients for the cultivation of degradative microbial consortia.
PubMed: Membrane Response to Diclofop Acid Is pH Dependent and Is Regulated by the Protonated Form of the Herbicide in Roots of Pea and Resistant and Susceptible Rigid Ryegrass.
PubMed: Resistance to Acetolactate Synthase-Inhibiting Herbicides in Annual Ryegrass (Lolium rigidum) Involves at Least Two Mechanisms.
PubMed: Aryl hydroxylation of the herbicide diclofop by a wheat cytochrome p-450 monooxygenase : substrate specificity and physiological activity.
PubMed: Determination of the herbicide diclofop in human urine.
PubMed: Effect of diclofop on the membrane potentials of herbicide-resistant and -susceptible annual ryegrass root tips.
PubMed: Coenzyme A esters of 2-aryloxyphenoxypropionate herbicides and 2-arylpropionate antiinflammatory drugs are potent and stereoselective inhibitors of rat liver acetyl-CoA carboxylase.
PubMed: Cross-Resistance to Herbicides in Annual Ryegrass (Lolium rigidum): IV. Correlation between Membrane Effects and Resistance to Graminicides.
PubMed: Cross-Resistance to Herbicides in Annual Ryegrass (Lolium rigidum) : III. On the Mechanism of Resistance to Diclofop-Methyl.
PubMed: Multiple forms of plant cytochromes p-450.
PubMed: Determination of diclofop-methyl and diclofop residues in soil and crops by gas chromatography.
PubMed: Effects of diclofop and diclofop-methyl on membrane potentials in roots of intact oat, maize, and pea seedlings.
PubMed: Cross-Resistance to Herbicides in Annual Ryegrass (Lolium rigidum) : II. Chlorsulfuron Resistance Involves a Wheat-Like Detoxification System.
PubMed: Cross-Resistance to Herbicides in Annual Ryegrass (Lolium rigidum): I. Properties of the Herbicide Target Enzymes Acetyl-Coenzyme A Carboxylase and Acetolactate Synthase.
PubMed: Diclofop-methyl increases the proton permeability of isolated oat-root tonoplast.
PubMed: Patterns of pesticide usage by cereal crop farmers in Western Australia.
PubMed: Kinetic characterization, stereoselectivity, and species selectivity of the inhibition of plant acetyl-CoA carboxylase by the aryloxyphenoxypropionic acid grass herbicides.
PubMed: Biochemical and histological effects of diclofop-methyl in mice and voles under laboratory conditions.
PubMed: Effects of diclofop and diclofop-methyl on the membrane potentials of wheat and oat coleoptiles.
PubMed: Herbicide levels in rivers draining two prairie agricultural watersheds (1984).
PubMed: Reciprocal Antagonism between the Herbicides, Diclofop-Methyl and 2,4-D, in Corn and Soybean Tissue Culture.
PubMed: Perturbation of Chara Plasmalemma Transport Function by 2[4(2',4'-Dichlorophenoxy)phenoxy]propionic Acid.
PubMed: Metabolism and selectivity of diclofop-methyl in wild oat and wheat.
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