Diclofop-Methyl

Basic Info

Common NameDiclofop-Methyl(F05055)
2D Structure
Description

Diclofop-methyl is a polycyclic alkanoic acid herbicide. Diclofop-methyl undergoes hydrolysis to form diclofop-acid a compound that also exhibits herbicidal properties. Diclofop-methyl was registered in Canada in 1977 and is sold under the tradename Hoe-Grass. Diclofop-methyl is used for postemergence control of wild oats, wild millets, and other annual grass weeds in wheat, barley, rye, red fescue, and broad-leaved crops such as soya beans, sugar beet, flax, legumes, potatoes, and cucumbers. Diclofop-methyl is a selective systemic herbicide that is used primarily in the prairies. It destroys the cell membrane, prevents the translocation of assimilates to the roots, reduces the chlorophyll content, and inhibits photosynthesis and meristem activity.

FRCD IDF05055
CAS Number51338-27-3
PubChem CID39985
FormulaC16H14Cl2O4
IUPAC Name

methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate

InChI Key

BACHBFVBHLGWSL-UHFFFAOYSA-N

InChI

InChI=1S/C16H14Cl2O4/c1-10(16(19)20-2)21-12-4-6-13(7-5-12)22-15-8-3-11(17)9-14(15)18/h3-10H,1-2H3

Canonical SMILES

CC(C(=O)OC)OC1=CC=C(C=C1)OC2=C(C=C(C=C2)Cl)Cl

Isomeric SMILES

CC(C(=O)OC)OC1=CC=C(C=C1)OC2=C(C=C(C=C2)Cl)Cl

Synonyms
        
            DICLOFOP-METHYL
        
            Methyldiclofop
        
            Diclofop methyl
        
            Illoxan
        
            51338-27-3
        
            Dichlorfop-methyl
        
            Hoegrass
        
            Hoelon
        
            Methyl diclofop
        
            Hoelon 3EC
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassDiphenylethers
Intermediate Tree NodesNot available
Direct ParentDiphenylethers
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
Substituents2-phenoxypropionic acid ester - Diphenylether - Phenoxyacetate - Diaryl ether - Phenoxy compound - Phenol ether - 1,3-dichlorobenzene - Alkyl aryl ether - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Methyl ester - Carboxylic acid ester - Ether - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organohalogen compound - Organochloride - Organooxygen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Properties

Property NameProperty Value
Molecular Weight341.184
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Complexity358
Monoisotopic Mass340.027
Exact Mass340.027
XLogP4.8
Formal Charge0
Heavy Atom Count22
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9240
Human Intestinal AbsorptionHIA+0.9872
Caco-2 PermeabilityCaco2+0.8110
P-glycoprotein SubstrateNon-substrate0.6590
P-glycoprotein InhibitorNon-inhibitor0.8000
Non-inhibitor0.9065
Renal Organic Cation TransporterNon-inhibitor0.8657
Distribution
Subcellular localizationMitochondria0.8551
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7841
CYP450 2D6 SubstrateNon-substrate0.8868
CYP450 3A4 SubstrateSubstrate0.5358
CYP450 1A2 InhibitorInhibitor0.9097
CYP450 2C9 InhibitorNon-inhibitor0.5096
CYP450 2D6 InhibitorNon-inhibitor0.9443
CYP450 2C19 InhibitorInhibitor0.8465
CYP450 3A4 InhibitorNon-inhibitor0.7846
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.7059
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9732
Non-inhibitor0.9168
AMES ToxicityNon AMES toxic0.8662
CarcinogensNon-carcinogens0.8197
Fish ToxicityHigh FHMT0.9863
Tetrahymena Pyriformis ToxicityHigh TPT0.9877
Honey Bee ToxicityHigh HBT0.7615
BiodegradationNot ready biodegradable0.8635
Acute Oral ToxicityIII0.7879
Carcinogenicity (Three-class)Non-required0.4354
Model Value Unit
Absorption
Aqueous solubility-4.5917LogS
Caco-2 Permeability1.1679LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7929LD50, mol/kg
Fish Toxicity-0.3644pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.7856pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Pig,MuscleJapan0.05ppm
Pig,KidneyJapan0.05ppm
Other Terrestrial Mammals,LiverJapan0.05ppm
WheatCanada0.1mg/kg
Other Poultry,EggsJapan0.05ppm
Chicken,EggsJapan0.05ppm
Other Poultry Animals,Edible OffalJapan0.05ppm
Chicken,Edible OffalJapan0.05ppm
Other Poultry Animals,KidneyJapan0.05ppm
Chicken,KidneyJapan0.05ppm
Other Poultry Animals,LiverJapan0.05ppm
Chicken,LiverJapan0.05ppm
Other Poultry Animals,FatJapan0.05ppm
Chicken,FatJapan0.05ppm
Other Poultry Animals,MuscleJapan0.05ppm
Chicken,MuscleJapan0.05ppm
MilkJapan0.05ppm
Other Terrestrial Mammals,Edible OffalJapan0.05ppm
Pig,Edible OffalJapan0.05ppm
Cattle,Edible OffalJapan0.05ppm

References

TitleJournalDatePubmed ID
Diclofop-methyl affects microbial rhizosphere community and induces systemic acquired resistance in rice.J Environ Sci (China)2017 Jan28115148
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.J Agric Food Chem2014 Nov 525307187
Degradation of cyhalofop-butyl (CyB) by Pseudomonas azotoformans strain QDZ-1 andcloning of a novel gene encoding CyB-hydrolyzing esterase.J Agric Food Chem2011 Jun 821534595
Enantioselective degradation and ecotoxicity of the chiral herbicide diclofop in three freshwater alga cultures.J Agric Food Chem2008 Mar 2618318497
One- and two-dimensional direct chiral liquid chromatographic determination ofmixtures of diclofop-Acid and diclofop-methyl herbicides.J Agric Food Chem2008 Apr 918338866
Enantiomeric resolution of chiral pesticides by high-performance liquidchromatography.J Agric Food Chem2006 Mar 816506803
Lolium rigidum, a pool of resistance mechanisms to ACCase inhibitor herbicides.J Agric Food Chem2005 Mar 2315769155
Tank-mix adjuvants and pesticide residues: some regulatory and quantitativeaspects.Pest Manag Sci2003 Nov14620051
Effect of cropping cycles and repeated herbicide applications on the degradation of diclofop-methyl, bentazone, diuron, isoproturon and pendimethalin in soil.Pest Manag Sci2002 Mar11975178
Comparative efficacy of five herbicides on winter cereal weeds in semi-aridregion of Algeria.Meded Rijksuniv Gent Fak Landbouwkd Toegep Biol Wet200112425104
Determination of diclofop-methyl and diclofop residues in soil and crops by gaschromatography.J Chromatogr1991 Jun 281894728