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100646-51-3

100646-51-3 Structure

100646-51-3 Structure
IdentificationMore
[Name]

Quizalofop-p-ethyl
[CAS]

100646-51-3
[Synonyms]

DPX-Y6202-31
ETHYL (R)-2-[4-(6-CHLORO-2-QUINOXALYLOXY)PHENOXY]PROPIONATE
QUINOFOP-P-ETHYL
QUIZALOFOP-P-ETHYL
2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-,ethylester,(r)-propanoicaci
assureii
ethyl(r)-2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)propanoate
nci-861094
Ethyl (R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionate
Propanoic acid, 2-4-(6-chloro-2-quinoxalinyl)oxyphenoxy-, ethyl ester, (2R)-
QUIZALOFOP-PETHYLESTER
2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-, ethyl ester, (r)-propanoic acid
DPX-Y6202
Ethyl (2R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propionate
EXP-3864
FBC-32197
Quizalofop ethyl ester
DPX-Y6202, Quinofop-ethyl, Ethyl (R)-2-[4-(6-chloro-2-quinoxalyloxy)phenoxy]propionate
ethyl-(RS)-2-[4-(6-chloro-2-quinoxalinyloxy) phenoxy] propanoate
Pilot Super
[Molecular Formula]

C19H17ClN2O4
[MDL Number]

MFCD01697481
[Molecular Weight]

372.8
[MOL File]

100646-51-3.mol
Chemical PropertiesBack Directory
[Melting point ]

76-77°C
[Boiling point ]

220 °C
[density ]

1.301±0.06 g/cm3(Predicted)
[Fp ]

>100 °C
[storage temp. ]

Store at 2-8°C
[solubility ]

Chloroform (Slightly), Methanol (Slightly)
[form ]

neat
[pka]

-1.39±0.48(Predicted)
[color ]

Light yellow to yellow
[Water Solubility ]

0.04 g/100 mL
[Henry's Law Constant]

4.8×103 mol/(m3Pa) at 25℃, Ebert et al. (2023)
[Major Application]

agriculture
environmental
[InChI]

InChI=1S/C19H17ClN2O4/c1-3-24-19(23)12(2)25-14-5-7-15(8-6-14)26-18-11-21-17-10-13(20)4-9-16(17)22-18/h4-12H,3H2,1-2H3/t12-/m1/s1
[InChIKey]

OSUHJPCHFDQAIT-GFCCVEGCSA-N
[SMILES]

C(OCC)(=O)[C@H](OC1=CC=C(OC2C=NC3C(N=2)=CC=C(Cl)C=3)C=C1)C
[CAS DataBase Reference]

100646-51-3(CAS DataBase Reference)
[EPA Substance Registry System]

100646-51-3(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302+H312-H413
[Precautionary statements ]

P264-P270-P273-P280-P301+P312-P302+P352+P312
[Hazard Codes ]

Xn
[Risk Statements ]

R21/22:Harmful in contact with skin and if swallowed .
[Safety Statements ]

S36/37:Wear suitable protective clothing and gloves .
[RIDADR ]

UN3077 9/PG 3
[WGK Germany ]

3
[RTECS ]

UA2458257
[HS Code ]

29333990
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Sodium hydroxide-->Thionyl chloride-->Phosphorus oxitrichloride-->Potassium carbonate-->Acetonitrile-->Sodium borohydride-->Hydroquinone-->Acetyl ketene-->Ethyl propionate-->Nitric oxide-->L(+)-Lactic acid-->4-Chloro-2-nitroaniline-->2,6-Dichloroquinoxaline-->Quizalofop-ethyl
[Preparation Products]

Quizalofop-ethyl E.C.
Hazard InformationBack Directory
[Uses]

Post-emergence herbicide for control of grassy weeds in broad-leaved crops. Herbicide.
[Definition]

ChEBI: Quizalofop-P-ethyl is an ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate that has R configuration. A proherbicide for quizalofop-P, it is used to control annual and perennial grass weeds in a variety of crops, including potatoes, sugar beet, peanuts, cotton and flax. It has a role as a proherbicide and an agrochemical. It is an ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate and a quinoxaline herbicide. It is functionally related to a quizalofop-P. It is an enantiomer of a (S)-quizalofop-ethyl.
[Production Methods]

Quizalofop-P-ethyl is commercially produced through a chiral synthesis starting with the etherification of 2,6-dichloroquinoxaline with hydroquinone under basic conditions to form 2-(6-chloroquinoxalin-2-yloxy)phenol, followed by stereoselective alkylation with ethyl (S)-2-bromopropionate (or resolution of the racemic ester via enzymatic or chiral crystallization methods) in the presence of potassium carbonate to yield the active compound.
[Mechanism of action]

Selective. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.
[Purification Methods]

This (±)-herbicide forms white crystals from Me2CO/EtOH and sublimes in vacuo. Large quantities can be distilled at high vacuum. Its solubilities at 20o in g/10mL are 0.09 (EtOH), 1.1 (Me2CO), 1.2 (xylene), 2.9 (*C6H6), and is nearly insoluble in H2O (0.3mg/L). The (±)-acid has [95977-28-9]. The R-ester enantiomer has m 76-77o (pale brown crystals from EtOH), [ ] D 20 + 3 5 . 9o (EtOH). It is the more active fatty acid synthase inhibitor (designated DPX-Y6202) used to control grassy weeds in broadleaf crops.
[Pesticide Type]

Herbicide
Spectrum DetailBack Directory
[Spectrum Detail]

Quizalofop-p-ethyl(100646-51-3)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

100646-51-3(sigmaaldrich)
100646-51-3 suppliers list
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