Diclofop

Basic Info

Common NameDiclofop(F06264)
2D Structure
FRCD IDF06264
CAS Number40843-25-2
PubChem CID38687
FormulaC15H12Cl2O4
IUPAC Name

2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid

InChI Key

OOLBCHYXZDXLDS-UHFFFAOYSA-N

InChI

InChI=1S/C15H12Cl2O4/c1-9(15(18)19)20-11-3-5-12(6-4-11)21-14-7-2-10(16)8-13(14)17/h2-9H,1H3,(H,18,19)

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            Diclofop [ANSI:BSI:ISO]
        
            Diclofop
        
            40843-25-2
        
            Diclofop acid
        
            DICHLORFOP ACID
        
            Caswell No. 328B
        
            2-(4-(2,4-Dichlorophenoxy)phenoxy)propanoic acid
        
            2-[4-(2,4-Dichlorophenoxy)phenoxy]propanoic acid
        
            HOE 21079
        
            BRN 2338390
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
Subclass2-phenoxypropionic acids
Intermediate Tree NodesNot available
Direct ParentAryloxyphenoxypropionic acids
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsAryloxyphenoxypropionic acid - Diphenylether - Phenoxyacetate - Diaryl ether - Phenoxy compound - Phenol ether - 1,3-dichlorobenzene - Alkyl aryl ether - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Carboxylic acid derivative - Carboxylic acid - Ether - Monocarboxylic acid or derivatives - Organooxygen compound - Organic oxygen compound - Carbonyl group - Organochloride - Organohalogen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aryloxyphenoxypropionic acids. These are aromatic compounds containing a phenoxypropionic acid that is para-substituted with an aryl group.

Properties

Property NameProperty Value
Molecular Weight327.157
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Complexity345
Monoisotopic Mass326.011
Exact Mass326.011
XLogP5
Formal Charge0
Heavy Atom Count21
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+0.9127
Human Intestinal AbsorptionHIA+0.9807
Caco-2 PermeabilityCaco2+0.7154
P-glycoprotein SubstrateNon-substrate0.6400
P-glycoprotein InhibitorNon-inhibitor0.8791
Non-inhibitor0.9235
Renal Organic Cation TransporterNon-inhibitor0.8833
Distribution
Subcellular localizationMitochondria0.9175
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7004
CYP450 2D6 SubstrateNon-substrate0.9167
CYP450 3A4 SubstrateNon-substrate0.5699
CYP450 1A2 InhibitorInhibitor0.6464
CYP450 2C9 InhibitorInhibitor0.5463
CYP450 2D6 InhibitorNon-inhibitor0.9346
CYP450 2C19 InhibitorNon-inhibitor0.6278
CYP450 3A4 InhibitorNon-inhibitor0.8833
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6473
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9703
Non-inhibitor0.9155
AMES ToxicityNon AMES toxic0.9598
CarcinogensNon-carcinogens0.8248
Fish ToxicityHigh FHMT0.9886
Tetrahymena Pyriformis ToxicityHigh TPT0.9927
Honey Bee ToxicityHigh HBT0.7039
BiodegradationNot ready biodegradable0.9006
Acute Oral ToxicityIII0.8428
Carcinogenicity (Three-class)Non-required0.4173
Model Value Unit
Absorption
Aqueous solubility-4.1595LogS
Caco-2 Permeability0.7790LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7320LD50, mol/kg
Fish Toxicity-0.5946pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8211pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Pears (Nashi pears/Oriental pears, Wild pears, Ya pears/Chinese white pears,)0130020European Union0.05*01/09/2008
Plums (American plums, Beach plums, Cherry plums /myrabolans, Chickasaw plums, Chinese jujubes/red dates/Chinese dates, Damsons/ bullaces, Gages/greengages/Reine Claudes, Japanese plums, Klamath pl...0140040European Union0.05*01/09/2008
Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E...0154010European Union0.05*01/09/2008
Pistachios0120100European Union0.05*01/09/2008
Walnuts0120110European Union0.05*01/09/2008
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.05*01/09/2008
Citrus fruits0110000European Union0.05*01/09/2008
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.05*01/09/2008
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.05*01/09/2008
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.05*01/09/2008
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.05*01/09/2008
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.05*01/09/2008
Others (2)0110990European Union0.05*01/09/2008
Tree nuts0120000European Union0.05*01/09/2008
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.05*01/09/2008
Brazil nuts0120020European Union0.05*01/09/2008
Cashew nuts0120030European Union0.05*01/09/2008
Chestnuts0120040European Union0.05*01/09/2008
Coconuts (Areca nuts/betel nuts,)0120050European Union0.05*01/09/2008
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.05*01/09/2008

References

TitleJournalDatePubmed ID
Diclofop-methyl affects microbial rhizosphere community and induces systemic acquired resistance in rice.J Environ Sci (China)2017 Jan28115148
Stereoselective Behavior of the Chiral Herbicides Diclofop-Methyl and DiclofopDuring the Soy Sauce Brewing Process.Chirality2016 Jan26501920
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
Lolium rigidum, a pool of resistance mechanisms to ACCase inhibitor herbicides.J Agric Food Chem2005 Mar 2315769155
Environmental effects of inclusion complexation between methylatedbeta-cyclodextrin and diclofop-methyl.J Agric Food Chem2005 Aug 2416104794
Tank-mix adjuvants and pesticide residues: some regulatory and quantitativeaspects.Pest Manag Sci2003 Nov14620051
Induction and inactivation of a cytochrome P450 confering herbicide resistance inwheat seedlings.Eur J Drug Metab Pharmacokinet2001 Jan-Jun11554440
Determination of diclofop-methyl and diclofop residues in soil and crops by gaschromatography.J Chromatogr1991 Jun 281894728