Quizalofop-ethyl

HCID 53518

Basic information

CAS
76578-14-8
Standard SMILES
CCOC(=O)C(C)Oc1ccc(Oc2cnc3cc(Cl)ccc3n2)cc1
InChIKey
OSUHJPCHFDQAIT-UHFFFAOYSA-N
Molecular formula
C19H17ClN2O4
Average molar mass
372.8 g/mol
Monoisotopic mass
372.0876847

Overview

Quizalofop-ethyl can cause male reproductive toxicity according to an independent committee of scientific and health experts.

Names & identifiers

Preferred name
Quizalofop-ethyl
IUPAC
ethyl 2-[4-(6-chloroquinoxalin-2-yl)oxyphenoxy]propanoate
English name
Quizalofop-ethyl
Molecular formula
C19H17ClN2O4
Molecular weight
372.8

Names & synonyms

QUIZALOFOP-ETHYL76578-14-8AssureTargaPilotDTXSID9023889Propanoic acid, 2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-, ethyl esterPropanoic acid, 2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]-, ethyl esterEXP 3864FBC 32197QUIZALOFOP ETHYL ESTERDTXCID903889
Show more names
nc302NC-302INY-6202nci96683NCI-96683All-in-oneQUIZALOOFOP
7280704RL4RefChem:872086CHEBI:81807Quizalofop ethylQuinofop-ethylXylofop-ethylQuizalofop-ethyl [ISO]Quizalofopethyl

Database identifiers

CAS
76578-14-8
PubChem CID
53518
DTXSID
DTXSID9023889
ChEMBL
CHEMBL444825
ChEBI
CHEBI:137937
UNII
7280704RL4
EC Number
616-351-3
Nikkaji
J22.972E

Properties

Computed structural properties

XLogP
4.3
Topological polar surface area
70.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
7
Heavy atoms
26

Experimental & physicochemical properties

Pesticides · 3 items

Pesticide -> EPA IRIS

Pesticides -> Herbicides, Other

Pesticide (Quizalofop ethyl) -> USDA PDB

LogP · 2 items

log Kow= 4.28

4.28

Density1.35 @ 20 °C
Color/FormColorless crystals
Solubility · 2 items

In benzene 290, xylene 120, acetone 111, ethanol 9, hexane 2.6 (all in g/l, at 20 °C)

In water, 0.3 mg/l @ 20 °C

Human DrugsPharmaceuticals

Physicochemical properties

Melting point
92 · 92-93°
Boiling point
0.2 · bp0.2 220°
Density
1.2671 · 1.2671 (rough estimate)
refractive index
1.68 · 1.6800 (estimate)
Flash point
100 °C · 100 °C
storage temp.
0 · 0-6°C

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 3 items

Hazard Traits - Reproductive Toxicity

Commission Regulation (EC) No 1490/2002

Propanoic acid, 2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelClass 9
Fire HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Health HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Hazards SummaryHigh-dose animal studies: Caused enlargement of liver cells; Not classifiable as to human carcinogenicity; [IRIS] May cause irritation; Can be absorbed through skin; [MSDSonline]
Reactive GroupAmines, Phosphines, and Pyridines

Safety & protection

Fire FightingExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
First AidExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Nonfire Spill ResponseExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Allowable Tolerances · 2 items

Tolerances are established for the combined residues of the herbicide quizalofop (2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propanoic acid) and quizalofop ethyl (ethyl-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propanoate), all expressed as quizaolgop ethyl, in or on the following agricultural commodities: soybean flour 0.5 ppm; soybean hulls 0.02 ppm; soybean meal 0.5 ppm; soybean soapstock 1.0 ppm; soybeans 0.05 ppm.

Tolerances are established for the combined residues of the herbicide quizalofop (2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propanoic acid), quizalop-ethyl (ethyl-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propanoate), and quizolofop-methyl (methyl-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propanoate), all expressed as quizalofop-ethyl, as follows: cattle, fat 0.05 ppm; cattle, meat 0.02 ppm; cattle, mbyp 0.05 ppm; eggs 0.02 ppm; goats, fat 0.05 ppm; goats, meat 0.02 ppm; goats, mbyp 0.05 ppm; hogs, fat 0.05 ppm; hogs, meat 0.02 ppm; hogs, mbyp 0.05 ppm; horses, fat 0.05 ppm; horses, meat 0.02 ppm; horses, mbyp 0.05 ppm; milk 0.01 ppm; milk, fat 0.05 ppm; poultry, fat 0.05 ppm; poultry, meat 0.02 ppm; poultry, mbyp 0.05 ppm; sheep, fat 0.05 ppm; sheep, meat 0.02 ppm; sheep, mbyp 0.05 ppm.

Personal Protective Equipment (PPE)Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Toxicology

Target OrgansHepatic
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 510 and 570(2) indicate that quizalofop-ethyl is expected to have low mobility in soil(SRC). Volatilization of quizalofop-ethyl from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.1X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 6.49X10-9 mm Hg(3) and water solubility, 0.3 mg/l(4). Quizalofop-ethyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). In a field dissipation study in soil, quizalofop-ethyl had a half-life of 60 days(2) suggesting that this compound is degraded fairly slowly in the environment.

AQUATIC FATE: Based on a classification scheme(1), Koc values of 510 and 570(2) indicate that quizalofop-ethyl is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may be expected(3) based upon a Henry's Law constant of 1.1X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 6.49X10-9 mm Hg(4) and water solubility, 0.30 mg/l(5). According to a classification scheme(6), an estimated BCF of 400(SRC), from its log Kow(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Data on the biodegradation of quizalofop-ethyl in water were not available. In a field dissipation study in soil, quizalofop-ethyl had a half-life of 60 days(2) suggesting that this compound is degraded fairly slowly in the environment.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), quizalofop-ethyl, which has a vapor pressure of 6.49X10-9 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase quizalofop-ethyl may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
EPA IRIS Information · 3 items

Assure

Hepatic

9 x 10 ^-3 mg/kg-day

Soil Adsorption/MobilityKoc values of 510 and 570(1) have been measured for quizalofop-ethyl in soil. According to a classification scheme(2), these Koc values suggest that quizalofop-ethyl has low mobility in soil.
Artificial Pollution SourcesQuizalofop-ethyl's production may result in its release to the environment through various waste streams; it's use as a herbicide(1) will result in its direct release to the environment(SRC).

Regulatory information

FIFRA Requirements · 1 item

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 128711; Type of Pesticide: conventional-herbicide; Use Site: food use and non-food use; Year: 1988.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
UA2458255
ridadr
UN3077 9/PG 3
hs_code
29333990
Toxicity
LD50 in male, female rats, male, female mice (mg/kg): 1670, 1480, 2350, 2360 orally; all 10,000 dermally; LC50 (96 hr) in rainbow trout: 10.7 mg/l (Sakata)

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationPesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
Absorption, Distribution and Excretion · 2 items

In mammals, following oral admin, the parent is rapidly metabolized; >90% of the dose is eliminated in the urine within 3 days.

Selective systemic herbicide, absorbed by the leaves, with translocation throughout the plant, moving in both the xylem & phloem. & accumulation in the meristematic tissue.

Uses & manufacturing

Uses · 5 items

Used as selective post-emergence herbicide for control of annual and perennial grass weeds in potatoes, soy beans, sugar beets, peanuts, vegetables, cotton, and other crops; [HSDB]

Farming (Pesticides) [Category: Industry]

For Quizalofop-ethyl (USEPA/OPP Pesticide Code: 128711) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Systemic herbicide used for selective post-emergence control of annual and perennial grass weeds in potatos, soy beans, sugar beet, peanuts, oilseed rape, sunflowers, vegetables, cotton, and flax.

This is a man-made compound that is used as a pesticide.

Methods of Manufacturing4-Chloro-o-phenylenediamine + glyoxylic acid + 2-(4-chlorophenoxy)propionic acid + ethanol (condensation/ether formation/esterification)
Formulations/Preparations · 2 items

USEPA/OPP Pesticide Code 128711; Trade Names: Targa, Assure, DPX-Y6202, INY-6202, NC 302, NCI-96683, FBC-32197, EXP-3864, Pilot.

Emulsifiable concentrate, suspension concentrate

Use ClassificationPharmaceuticals
Applications · 3 items

UsesQuizalofop-ethyl is a selective postemergence herbicide used to control both annual and perennial grasses in soybeans and cotton.

UsesHerbicide.

General DescriptionWhite crystals. Insoluble in water. Used as an herbicide.

Upstream & downstream products

Suppliers46 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]
河南赢创生物科技有限公司16650615803 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
河北枫嘉新材料科技有限公司+86-0311-87836622 +86-18712993135 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate is an ethyl ester resulting from the formal condensation of the carboxy group of 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid with ethanol. It is an ethyl ester, an organochlorine compound, a quinoxaline derivative and an aromatic ether. It is functionally related to a 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid.

Related reactions

3 records

Compound notes

Loading…