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Chlorfenac

HCID 6805
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Basic information

CAS
85-34-7
Standard SMILES
O=C(O)Cc1c(Cl)ccc(Cl)c1Cl
InChIKey
QZXCCPZJCKEPSA-UHFFFAOYSA-N
Molecular formula
C8H5Cl3O2
Average molar mass
239.5 g/mol
Monoisotopic mass
237.935512

Overview

Chlorfenac is a member of the class of phenylacetic acids that is phenylacetic acid in which the phenyl group has been substituted by chlorines at positions 2, 3, and 6. An obsolete herbicide that was used as its sodium and ammonium salts. It has a role as a herbicide, a synthetic auxin and an agrochemical. It is a member of phenylacetic acids and a trichlorobenzene. It is a conjugate acid of a chlorfenac(1-).

Names & identifiers

Preferred name
Chlorfenac
IUPAC
2-(2,3,6-trichlorophenyl)acetic acid
English name
CHLORFENAC
Molecular formula
C8H5Cl3O2
Molecular weight
239.48

Names & synonyms

Chlorfenac85-34-7FenacKaneparFenaeTri-fen2,3,6-TRICHLOROPHENYLACETIC ACIDTrifeneTri-fene2,3,6-Trichlorobenzeneacetic acidTri feneAcetic acid, (2,3,6-trichlorophenyl)-
Show more names
FENACACIDNSC 41931
Benzeneacetic acid, 2,3,6-trichloro-2,3,6-TCA2,3,6-TrichlorphenylessigsaeureDTXSID20402848SOV3EP1QG2,3,6-Trichlorophenyl acetic acidNSC-41931DTXCID0020284

Database identifiers

CAS
85-34-7
PubChem CID
6805
DTXSID
DTXSID2040284
ChEMBL
CHEMBL1895774
ChEBI
CHEBI:82235
UNII
8SOV3EP1QG
EC Number
201-599-3
Nikkaji
J4.916F

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
13
Formal charge
0
Complexity
198

Experimental & physicochemical properties

SpringerMaterials PropertiesFusion temperature
PesticidesPesticides -> Herbicides, Chlorophenoxy
LogP · 2 items

3.20

3.2

Color/Form · 2 items

CRYSTALS FROM BENZENE

COLORLESS SOLID

Solubility · 2 items

SOL IN ACETONE, ALC, ETHER

200 MG/L WATER @ 28 °C; SOL IN MOST ORGANIC SOLVENTS

CorrosivityNON-CORROSIVE
Melting Point161 °C
Vapor Pressure · 2 items

0.0000339 [mmHg]

1.7x10-5 mm Hg at 25 °C

Physical DescriptionColorless solid; [HSDB] White solid; [MSDSonline]
Stability/Shelf LifeNo shelf life limitations. Not harmed by freeze thaw cycles.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

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

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Warning

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

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Hazard information

Fire PotentialNonflammable
Hazards SummaryEmergency treatment: Chlorophenoxy compounds; [HSDB] May cause irritation; [MSDSonline] See 2,4,5T.
FIFRA Requirements · 2 items

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Trichlorophenylacetic acid is found on List D. Case No: 4020; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Trichlorophenylacetic acid; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Chemistry & industry

Pharmacology

Metabolism/Metabolites52.8% OF DOSE WAS EXCRETED IN URINE OF LACTATING COW AS 2,3,6-TRICHLOROPHENYLACETIC ACID ESTER GLUCURONIDE ... .
Absorption, Distribution and Excretion · 2 items

52.8% OF A DOSE WAS EXCRETED IN THE URINE OF A LACTATING COW AS 2,3,6-TRICHLOROPHENYLACETIC ACID ESTER GLUCURONIDE & 18.6% AS THE FREE ACID. FENAC COMPONENTS WERE NOT EXCRETED BY EITHER THE FECAL OR MAMMARY ROUTES. FENAC WAS UNMETABOLIZED BY LIVER DRUG-METABOLIZING ENZYMES & RUMINAL MICROFLORA.

No significant ... percutaneous absorption ... .

Uses & manufacturing

Uses · 4 items

Used as an herbicide; No longer contained in any registered pesticide products; [HSDB]

Farming (Pesticides) [Category: Industry]

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

HERBICIDE /SRP: FORMER USE/

Methods of ManufacturingPREPARED BY CONVERSION OF 2,3,6-TRICHLOROTOLUENE TO THE BENZYL CHLORIDE, THE BENZYL CYANIDE, THEN HYDROLYSIS ... .
Formulations/Preparations · 2 items

`FENATROL', AQUEOUS CONCENTRATE OF CHLORFENAC-SODIUM; ALSO MIXTURES: CHLORFENAC + AMINOTRIAZOLE + ATRAZINE; CHLORFENAC + BROMACIL; CHLORFENAC + 2,4-D.

FENAC CONSISTS OF 70% OF 2,3,6-TRICHLOROPHENYLACETIC ACID & 30% OF STRUCTURAL ISOMERS.

Use ClassificationHERBICIDES
General Manufacturing Information · 4 items

Benzeneacetic acid, 2,3,6-trichloro-: ACTIVE

... USUALLY APPLIED AS SODIUM SALT, IS ... ABSORBED PRIMARILY BY ROOTS ... USED TO CONTROL ANNUAL GRASSES, BROAD-LEAVED WEEDS, FIELD BINDWEED, COUCH GRASS & OTHER PERENNIAL WEEDS IN INDUST & OTHER NON-CROP SITUATIONS @ RATES UP TO 18 KG AE/HA. ... ALSO USED FOR PRE-EMERGENCE WEED CONTROL IN SUGARCANE ... .

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Dissociation ConstantspKa= 3.70
Other Experimental Properties · 2 items

It forms water-soluble salts with alkalis.

1.1 Pa @ 100 °C

Physicochemical properties

Melting point
161 °C · 161 °C
Boiling point
341.55 °C · 341.55°C (rough estimate)
Density
1.568 · 1.568
refractive index
1.4521 · 1.4521 (estimate)
storage temp.
0 · 0-6°C
pka
3.63 · 3.63±0.10(Predicted)
color
Colorless crystals
Water Solubility
0.2 g/L · 0.2g/L(28 ºC)
Merck
13 · 13,2103
BRN
2113332 · 2113332
Henry's Law Constant
8.3 · 8.3×10-1 mol/(m3Pa) at 25℃, Mackay et al. (2006)
EWG's Food Scores
1 · 1
FDA UNII
8 SOV3EP1QG · 8SOV3EP1QG
EPA Substance Registry System
Chlorfenac (85-34-7)
Symbol(GHS)
7 · GHS07,GHS09
Signal word
Warning
Hazard statements
302 · H302+H312-H411
Precautionary statements
264 · P264-P270-P273-P280-P301+P312-P302+P352+P312
Hazard Codes
N-Xn,N,Xn
Risk Statements
51 · 51/53-22
Safety Statements
61 · 61-36-45-26
RIDADR
3077 · 3077
WGK Germany
2 · 2
RTECS
8750000 · AJ8750000
TSCA
TSCA listed
HS Code
29163990 · 29163990
Hazardous Substances Data
85 · 85-34-7(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in rats: 3000 mg/kg (Bailey, White)

A tolerance is established for negligible residues of the herbicide 2,3,6-trichlorophenylacetic acid in or on sugarcane, such residues resulting from application of its dimethylamine or sodium salts.

Hazard Classes and Categories · 3 items

Acute Tox. 4 (100%)

Acute toxicity - category 4

Acute Tox. 4 *

Safety & protection

Preventive MeasuresCleaning glassware and spray equipment: Washes clean with water. Standard washing detergent aid may be used.
Allowable TolerancesA tolerance of 0.1 ppm is established for negligible residues of the herbicide 2,3,6-trichlorophenylacetic acid in or on sugarcane, such residues resulting from application of its dimethylamine or sodium salts.

Toxicology

Ecotoxicity Values · 5 items

LC50 BOBWHITE QUAIL, 14 DAY OLD, ORAL GREATER THAN 5000 PPM (NO MORTALITY TO 5000 PPM)

LC50 JAPANESE QUAIL, 14 DAY OLD, ORAL GREATER THAN 5000 PPM (NO MORTALITY TO 5000 PPM)

LC50 RING-NECKED PHEASANTS, 10 DAY OLD, ORAL GREATER THAN 5000 PPM (NO MORTALITY TO 5000 PPM)

LC50 MALLARD DUCKS, 10 DAY OLD, ORAL GREATER THAN 5000 PPM (NO MORTALITY TO 5000 PPM)

For more Ecotoxicity Values (Complete) data for 2,3,6-TRICHLOROPHENYLACETIC ACID (11 total), please visit the HSDB record page.

Environmental Fate · 5 items

TERRESTRIAL FATE: OVER A 3 YR PERIOD, HIGHEST CONCN IN LOSS FROM RUNOFF WERE USUALLY ASSOCIATED WITH RAINSTORMS THAT OCCURRED SOON AFTER APPLICATION. MAXIMAL SEASONAL LOSSES WERE 2.90% OF THE APPLIED FENAC

TERRESTRIAL FATE: ... RESISTS DECOMPOSITION IN SOIL MUCH LONGER THAN ... /CHLOROPHENOXACETIC ACIDS/.

TERRESTRIAL FATE: If released to soil, estimated soil adsorption coefficients ranging from 237 to 1311(1) indicate low to moderate mobility for 2,3,6-trichlorophenylacetic acid(SRC) based on a suggested classification scheme(2). Due to its high degree of ionization at environmental pHs, percent organic matter, clay content, and soil pH are also important factors in determining its degree of adsorption(3). An estimated vapor pressure for 2,3,6-trichlorophenylacetic acid of 1.7x10-5 mm Hg at 25 °C(4) and estimated Henry's Law constant of 1.8x10-8 atm-cu m/mole at 25 °C(5) indicate that important. Biodegradation of 2,3,6-trichlorophenylacetic acid in soil under both aerobic and anaerobic conditions is slow based on data from both laboratory(6) and field experiments(7) although it may be subject to enhanced degradation through cometabolic processes(8).

AQUATIC FATE: If released to water, 2,3,6-trichlorophenylacetic acid is expected to persist for long periods of time. No degradation of 2,3,6-trichlorophenylacetic acid was observed when it was incubated with lake water/sediment or activated sludge under aerobic conditions or when incubated with a sandy loam soil in water under anaerobic conditions(1). Biodegradation studies with soil inoculum and added nutrients produced an enhanced removal rate(1) suggesting that cometabolic process may be important(2). Adsorption of 2,3,6-trichlorophenylacetic acid to sediment may be important based on estimated soil adsorption coefficients ranging from 237 to 1311(3) determined from its water solubility, 200 mg/L(4), and octanol/water partition coefficient, 3.20(5). Laboratory studies have indicated rapid adsorption to sediment(1) although pH, percent organic matter, and clay content of sediment may also be important in determining the degree of adsorption due to 2,3,6-trichlorophenylacetic acid's high degress of ionization at environmental pHs(6-7).

For more Environmental Fate (Complete) data for 2,3,6-TRICHLOROPHENYLACETIC ACID (6 total), please visit the HSDB record page.

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.
Acute Toxicity LinkChemical: FENAC
Effluent Concentrations2,3,6-Trichlorophenylacetic acid was detected in farm field runoff from treated sugarcane plots at 2 to 310 ppb in rain events up to 6 months after application(1).
Soil Adsorption/Mobility · 2 items

Experimental soil adsorption coefficients ranging from 0.3 to 667 on four different sediments with percent organic carbon ranging from 0.3 to 54 were observed at pH 6.5; adsorption on organic muck was found to increase at pH 4.5 but not at pH 9(1). Soil pH, especially in the range 5.0-6.7, was described as the most important factor in 2,3,6-trichlorophenylacetic acid mobility(2-3). At neutral or basic pHs, 2,3,6-trichlorophenylacetic acid will exist predominately as the ionized acid and adsorption to soil will driven by ionic interactions between it and the soil while at more acidic pHs hydrophobic processes will predominate(4). Soil TLC experiments using a wide range of soils (Hagerstown silty clay loam, Lakeland sandy loam, Chillium silt loam) produced Rfs ranging from 0.38 to 1.0 indicating that 2,3,6-trichlorophenylacetic acid has a high degree of mobility compared to other pesticides(2-6).

Based on an experimental log Kow of 3.20 for 2,3,6-trichlorophenylacetic acid, obtained in 0.1 and 0.5 M HCl(1), and its water solubility, 280 mg/L at 28 °C(2), estimated soil adsorption coefficients ranging from 159 to 1311 can be calculated using an appropriate regression equation(3). According to a suggested classification scheme(4), these values suggest that 2,3,6-trichlorophenylacetic acid will display moderate to high mobility in soil. A Koc of 170 has been estimated for 2,3,6-trichlorophenylacetic acid based on its heat of solution(5). In a scale on mobility of pesticides in soil ranging from 1, immobile, to 5, highly mobile, 2,3,6-trichlorophenylacetic acid was placed in mobility class 4(6).

Natural Pollution Sources2,3,6-Trichlorophenylacetic acid is of anthropogenic origin, and it is not known to be produced by natural sources. (SRC)
Human Toxicity Excerpts · 1 item

SYMPTOMATOLOGY (PARTLY INFERENTIAL): 1. FATIGUE, WEAKNESS, ANOREXIA; PERHAPS NAUSEA, VOMITING & DIARRHEA. 2. HYPOREFLEXIA & LETHARGY PROGRESSING TO COMA, WITH CONSTRICTED PUPILS (MIOSIS). 3. FLACCID PARALYSIS HAS BEEN DESCRIBED IN ONE COMATOSE PT & GRAND MAL CONVULSIONS WITH OPISTHOTONOS IN ANOTHER, HYPERTONIA WITH AREFLEXIA IN A THIRD, & TWITCHING & JERKING IN A FOURTH. ... 5. PROGRESSIVE DECLINE IN BLOOD PRESSURE WITH DEATH IN DEEP COMA. THE POSSIBILITY THAT HYPERPYREXIA & HYPERMETABOLISM MAY HAVE CONTRIBUTED TO THE FATAL OUTCOME DOES NOT APPEAR TO HAVE BEEN RULED OUT (ONE COMATOSE PATIENT WAS DESCRIBED AS SWEATING PROFUSELY). A TERMINAL PNEUMONIA IS LIKELY. 6. DISTURBANCES IN BODY TEMP REGULATION MAY BE ENCOUNTERED. PERHAPS SEVERE REDUCTION OF BODY TEMP IN COOL OR COLD ENVIRONMENTS. MORE PROBABLY, FEBRILE RESPONSES IN WARM ENVIRONMENTS OR DURING EXERCISE. 7. PROGRESSIVE HYPOTENSION WITH DEATH IN PERIPHERAL VASCULAR COLLAPSE, PERHAPS ASSOCIATED WITH ACIDOSIS DUE TO LACTIC ACIDEMIA & OTHER PRODUCTS OF HYPERMETABOLISM. 8. IN NONFATAL POISONINGS, SEVERE & PROTRACTED ... /PRC: NEUROPATHY/ WITH PAIN, PARESTHESIAS & WEAKNESS. ... HUMANS HAVE EXPERIENCED MUSCLE FASCICULATIONS AS WELL AS MYOTONIA. CHRONIC EXPOSURE MAY LEAD TO CENTRAL NERVOUS SYSTEM DEFECTS IN THE CONTROL OF MOTOR FUNCTION. /2,4-D/

Artificial Pollution Sources · 1 item

2,3,6-Trichlorophenylacetic acid was used as both a pre- and post-emergence herbicide to control annual grasses, broad-leaved weeds(1) and to control submerged aquatic weeds(2). Use of 2,3,6-trichlorophenylacetic acid as a herbicide results in direct application to the environment and is, therefore, its primary environmental emission source(SRC).

Environmental Biodegradation · 2 items

No degradation of 2,3,6-trichlorophenylacetic acid was observed when incubated with lake water/sediment or activated sludge under aerobic conditions or with a sandy loam soil in water under anaerobic conditions(1). More than 75% of 2,3,6-trichlorophenylacetic acid remained after 120 day biodegradation studies in lake water (Oneida Lake, NY), primary sewage effluent, soil, and soil/water suspensions; adding supplemental nutrients deceases the amount remaining to 40% after 120 days in soil inoculum while little effect was observed using other media. Cometabolic degradation may be the major biodegradation process for 2,3,6-trichlorophenylacetic acid in aquatic systems(2). A dichlorohydroxybenzene derivative was tentatively identified as a product of the biodegradation of 2,3,6-trichlorophenylacetic acid in soil(2). 2,3,6-Trichlorophenylacetic acid was described as being susceptible to decarboxylation reactions when incubated with soil inoculum(3).

Two years after soil application of 2,3,6-trichlorophenylacetic acid, crop injury was observed and used to describe its presence and thus resistance to biodegradation in soil(1-2). A field study at 6 different soil type locations indicated that 2,3,6-trichlorophenylacetic acid was persistent in soil as residues remained 18 months after spraying(2). Residues of 2,3,6-trichlorophenylacetic acid in water and sediment samples of 0.38 ppm and 0.26 ppm, respectively, were found 160 days after an initial application of 1.56 ppm to a pond(3).

Sediment/Soil ConcentrationsResidues of 2,3,6-trichlorophenylacetic acid in sediment samples of 0.26 ppm were found 160 days after an initial application of 1.56 ppm to a pond(1).
Environmental Bioconcentration · 1 item

Experimental bioconcentration factors ranging from 1.6 to 11.6 in bluegills (Lepomis macrochirus) were determined in static tests with a 2,3,6-trichlorophenylacetic acid concentration of 2 ppm(1). Based on an experimental log Kow of 3.20 for 2,3,6-trichlorophenylacetic acid, obtained in 0.1 and 0.5 M HCl(2), and its water solubility, 200 mg/L at 28 °C(3), estimated bioconcentration factors ranging from 31 to 159 can be calculated(SRC) using an appropriate regression equation(4). The magnitude of these values indicate that bioconcentration in fish and aquatic organisms will not be a significant process(SRC).

Regulatory information

FIFRA Requirements · 2 items

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Trichlorophenylacetic acid is found on List D. Case No: 4020; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Trichlorophenylacetic acid; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

A tolerance is established for negligible residues of the herbicide 2,3,6-trichlorophenylacetic acid in or on sugarcane, such residues resulting from application of its dimethylamine or sodium salts.

Safety data

wgk
2
tsca
TSCA listed
rtecs
AJ8750000
ridadr
3077
hs_code
29163990
Toxicity
LD50 orally in rats: 3000 mg/kg (Bailey, White)
risk_code
51/53-22
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
hazard_code
N-Xn,N,Xn
safety_code
61-36-45-26
Hazard statements
H302+H312-H411
Precautionary statements
P264-P270-P273-P280-P301+P312-P302+P352+P312
Hazardous Substances Data
85-34-7(Hazardous Substances Data)

EFFECTIVE AGAINST SUBMERGED AQUATIC WEEDS WHEN APPLIED TO SOIL BEFORE FLOODING.

Closely related to silvex.

Applications · 3 items

DescriptionChlorfenac is an obsolete herbicide for the control of annual weeds and grasses. It has a low aqueous solubility and is highly volatile. It may be persistent in both soil and water systems. It is moderately toxic to aquatic fife but has a low toxicity to birds. It is moderately toxic to mammals if ingested.

UsesChlorfenac is a herbicide used in agriculture for weed control mainly in sugar canes as well as other crops.

UsesHerbicide.

Additional notes · 1 item

DefinitionChEBI: Chlorfenac is a member of the class of phenylacetic acids that is phenylacetic acid in which the phenyl group has been substituted by chlorines at positions 2, 3, and 6. An obsolete herbicide that was used as its sodium and ammonium salts. It has a role as a herbicide, an agrochemical and a synthetic auxin. It is a trichlorobenzene and a member of phenylacetic acids. It is a conjugate acid of a chlorfenac(1-).