Grundinformationen
- CAS
16484-77-8- Standard-SMILES
Cc1cc(Cl)ccc1O[C@H](C)C(=O)O- InChIKey
WNTGYJSOUMFZEP-SSDOTTSWSA-N- Summenformel
- C10H11ClO3
- Durchschnittliche Molmasse
- 214,64 g/mol
- Monoisotopische Masse
- 214,0396719
Überblick
(R)-mecoprop is the (R)-enantiomer of 2-(4-chloro-2-methylphenoxy)propanoic acid; the active stereoisomer of the racemic herbicide mecoprop. It has a role as a phenoxy herbicide. It is a conjugate acid of a (R)-2-(4-chloro-2-methylphenoxy)propanoate. It is an enantiomer of a (S)-mecoprop.
Namen und Bezeichner
- Bevorzugter Name
- Mecoprop-P
- IUPAC
- (2R)-2-(4-chloro-2-methylphenoxy)propanoic acid
- Lokaler Name
- (R)-2-(4-Chlor-2-methylphenoxy)propionsure
- Englischer Name
- MECOPROP-P
- Summenformel
- C10H11ClO3
- Molmasse
- 214.65
Namen und Synonyme
Mecoprop-P16484-77-8(R)-MecopropMecoprop-P [ISO]Duplosan KVMecoprop, D-DTXSID3032670(R)-MCPPEINECS 240-539-0UNII-455R9M917HIPPONJIME EKIZAIPropanoic acid, 2-(4-chloro-2-methylphenoxy)-, (R)-
Weitere Namen anzeigen
D(+)-MECOPROP2m-4xpOPTICA(R)Astix(TM)duplosankvDUPLOSAN(R) KV
(R)-2-(4-Chloro-2-methylphenoxy)propionate(+)-MECOPROP455R9M917H(R)-(+)-MECOPROPPropanoic acid, 2-(4-chloro-2-methylphenoxy)-, (2R)-DTXCID1012670CHEBI:75703EC 240-539-0
Datenbank-Bezeichner
- CAS
16484-77-8- PubChem CID
- 185588
- DTXSID
DTXSID3032670- ChEMBL
CHEMBL2145254、CHEMBL2287189- ChEBI
CHEBI:75703- UNII
- 455R9M917H
- EC Number
- 240-539-0
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,1
- Polarare Oberfläche (TPSA)
- 46,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 208
Experimentelle und physikochemische Eigenschaften
SpringerMaterials PropertiesFusion temperature
Pesticides
Herbicides
Active substance -> EU Pesticides database: Approved
Pesticides -> Herbicides, Chlorophenoxy
Environmental transformation -> Pesticides (parent, predecessor)
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionColorless odorless solid; [Reference #1]
Physikochemische Eigenschaften
- Schmelzpunkt
- 95 °C · 95 °C
- Siedepunkt
- 308.11 °C · 308.11°C (rough estimate)
- Dichte
- 1.2413 · 1.2413 (rough estimate)
- Dampfdruck
- 0.001 Pa · 0.001Pa at 25℃
- Brechungsindex
- 1.539 · 1.5390 (estimate)
- Flammpunkt
- 100 °C · >100 °C
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P330, P391, and P501 (click each P-code to see the statement)
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P330, P391, and P501 (click each P-code to see the statement)
Gefahrenhinweise
Regulatory Information
Commission Regulation No 844/2012
MCPP-p acid + salts is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
03/70/EC, Dir. 03/70/EC, Reg (EU) 2026/2025, Reg. (EU) 2016/2016, Reg. (EU) 2016/2016, Reg. (EU) 2018/1796, Reg. (EU) 2018/1796, Reg. (EU) 2018/84, Reg. (EU) 2018/84, Reg. (EU) 2019/2094, Reg. (EU) 2019/2094, Reg. (EU) 2021/2068, Reg. (EU) 2021/52, Reg. (EU) 2024/324, Reg. (EU) 2025/787 , Reg. (EU) No 2023/114, Reg. (EU) No 540/2011, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012, Reg. (EU) No 823/2012
REACH registered substance: mecoprop-P (ISO); (R)-2-(4-chloro-2-methylphenoxy)propionic acid (EC: 240-539-0)
Mecoprop-p: HSNO Approval: HSR003313 Approved with controls
Hazards SummaryThe potassium salt and dimethylamine salt dissociate to the MCPP-p acid. The mixture of isomers (Mecoprop) and the active isomer (MCPP-p) have similar toxic effects. {Reference #1] See Mecoprop and Mecoprop dimethylamine salt.
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute toxicity (ingestion) - category 4
Acute Tox. 4
Toxikologische Informationen
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
CDDs are absorbed through oral, inhalation, and dermal routes of exposure. CDDs are carried in the plasma by serum lipids and lipoproteins, distributing mainly to the liver and adipose tissue. CDDs are very slowly metabolized by the microsomal monooxygenase system to polar metabolites that can undergo conjugation with glucuronic acid and glutathione. They may increase the rate of their own metabolism by inducing CDDs induce both phase I and phase II enzymes. The major routes of excretion of CDDs are the bile and the feces, though smaller amounts are excreted in the urine and via lactation. (L177)
Verwendung und Herstellung
Uses
Used as a plant growth regulator (herbicide); The R isomer has been identified as the herbicidally active isomer and with advances in chemical synthesis can now be affordably commercially manufactured; This enriched isomeric form is being called Mecoprop-p (MCPP-p) and is replacing the racemic mixture in all formulations being used in the US; [Reference #1]
Dioxins occur as by-products from the manufacture of organochlorides, the bleaching of paper, chlorination by waste and drinking water treatment plants, municipal solid waste and industrial incinerators, and natural sources such as volcanoes and forest fires. (L177, L178)
Household Products
Information on 8 consumer products that contain Mecoprop-p in the following categories is provided:
Information on 14 consumer products that contain d-Mecoprop in the following categories is provided:
Use ClassificationEnvironmental transformation -> Pesticides (parent, predecessor)
Anwendungen
VerwendenMecoprop-P has been used as a reference standard for identification of mecoprop enantiomer elution using chiral GC columns. It has also been used as a pesticide in a comparative study to detect the pesticide contamination of indoor air and human hair samples.
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