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Chlorfenson

HCID 6635
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Basic information

CAS
80-33-1
Standard SMILES
O=S(=O)(Oc1ccc(Cl)cc1)c1ccc(Cl)cc1
InChIKey
RZXLPPRPEOUENN-UHFFFAOYSA-N
Molecular formula
C12H8Cl2O3S
Average molar mass
303.2 g/mol
Monoisotopic mass
301.9571207

Overview

Chlorfenson is an arenesulfonic acid.

Names & identifiers

Preferred name
Chlorfenson
IUPAC
(4-chlorophenyl) 4-chlorobenzenesulfonate
English name
OVEX
Molecular formula
C12H8Cl2O3S
Molecular weight
303.16

Names & synonyms

ChlorfensonOvex80-33-1OrthotranDifensonOvochlorEstonmiteOvatranOvotoxOvotranEster sulfonateBenzolsulfonate
Show more names
CCSd854OnexCPCBC-854D 854k-101k6451
ChlorofenizonEphirsulphonateEthersulfonateTrichlorfensonChlorfensinCorotranNiagaratranOrochlor

Database identifiers

CAS
80-33-1
PubChem CID
6635
DTXSID
DTXSID5020310
ChEMBL
CHEMBL499017
ChEBI
CHEBI:82155
UNII
LW65NJ3YWV
EC Number
201-270-4
Nikkaji
J3.852K

Properties

Computed structural properties

XLogP
4.3
Topological polar surface area
51.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
18
Formal charge
0
Complexity
350

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesFusion temperature
Pesticides · 4 items

Acaricides, Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organochlorine Pesticides

Pesticide (Ovex) -> USDA PDB

Color/Form · 2 items

CRYSTALS FROM BENZENE

White, crystalline solid

Solubility · 3 items

PRACTICALLY INSOL IN WATER; SOL @ 25 °C IN G/100 ML: 1.4 G IN 95% ALCOHOL; 41.0 G IN CARBON TETRACHLORIDE; 110.0 G IN CYCLOHEXANONE; 110.0 G IN ETHYLENE DICHLORIDE; 2.0-2.7 G IN PETROLEUM OILS; 130.0 G IN ACETONE; 78 G IN XYLENE

SOLUBLE IN AROMATIC SOLVENTS, ACETONE; INSOLUBLE IN WATER

SOL IN 100 G SOLVENT @ 25 °C: 1 G IN ETHYL ALC; 2 G IN KEROSENE

CorrosivityNoncorrosive
Melting Point · 2 items

86.5 °C

WHITE TO TAN FLAKY SOLID; MP: APPROX 80 °C /TECHNICAL/

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, P280, P301+P317, P302+P352, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

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

P264, P270, P273, P280, P301+P317, P302+P352, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information2002/2076
Hazards SummaryA skin irritant; [HSDB] A skin irritant; May cause CNS depression; [MSDSonline]
Special ReportsToxicology Review: Residue Reviews 56: 107 (1975)
Hazard Classes and Categories · 3 items

Acute Tox. 4 (100%)

Acute toxicity - category 4

Acute Tox. 4 *

Skin, Eye, and Respiratory IrritationsCAUSES SKIN IRRITATION IN MAN...

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

Chlorfenson is a topical solution applied once-daily on affected nails during treatment periods of 3-6 months. In pilot studies, Chlorfenson has shown promising results and provides important benefits compared to existing treatment alternatives. There is a significant need for more efficacious topical treatments. For more severe cases of the disease where more than 50% of the nail is affected, the only available options are oral anti-fungals which are associated with a certain risk for severe side effects.

Metabolism/Metabolites · 1 item

WHEN INJECTED INTO THE ABDOMEN OF THE AMERICAN COCKROACH, DECOMPOSITION...GAVE RISE TO P-CHLOROBENZENESULFONIC ACID. IN CITRUS SAPLING & SOYBEAN SEEDLING, THE ACARICIDE PENETRATED INTO THE PLANT & WAS DECOMPOSED TO P-CHLOROBENZENESULFONIC ACID & OTHER CMPD.

Uses & manufacturing

Uses · 6 items

Used as insecticide and acaricide (ovicide with long residual activity) for cotton, nuts, vegetables, and ornamentals; No longer produced in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

FORMER USE: MITICIDE

Effective as an ovicide with long residual effect. For cotton, deciduous fruits, nuts, and ornamentals. Shows evidence of powdery mildew control.

Insecticide and acaricide

Chlorfenson, characterized by its long residual ovicidal activity, is used against mites on citrus, fruit, vegetables, and ornamentals.

U.S. Production · 2 items

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

Methods of ManufacturingProduction is by condensation of 4-chlorobenzenesulfonyl chloride with 4-chlorophenol under basic conditions.
Formulations/Preparations · 3 items

AS WETTABLE POWDERS (40% & 50%); EMULSIFIABLE CONCN; 5% & 10% DUSTS

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Vapor Pressure · 2 items

0.00000188 [mmHg]

Negligible at 25 °C

Physical DescriptionWhite solid; [Hawley]
Stability/Shelf LifeHYDROLYZES IN ALKALI
Collision Cross Section158.08 Ų [M]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+]

Physicochemical properties

Melting point
86.5 · 86.5-86.8°
Boiling point
429.6 · 429.6±45.0 °C(Predicted)
Density
1.4572 · 1.4572 (estimate)
storage temp.
0 · 0-6°C
form
Crystalline
biological source
human blood
BRN
2944674 · 2944674
Henry's Law Constant
6.2 · 6.2×101 mol/(m3Pa) at 25℃, HSDB (2015)
Major Application
agricultureenvironmental
Cosmetics Ingredients Functions
ANTIMICROBIAL
InChI
1S/C12H8Cl2O3S/c13-9-1-5-11(6-2-9)17-18(15,16)12-7-3-10(14)4-8-12/h1-8H
InChIKey
RZXLPPRPEOUENN-UHFFFAOYSA-N
SMILES
Clc1ccc(OS(=O)(=O)c2ccc(Cl)cc2)cc1
EWG's Food Scores
1 · 1-2
FDA UNII
65 NJ3YWV · LW65NJ3YWV
EPA Substance Registry System
Chlorfenson (80-33-1)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07,GHS09
Signal word
Warning
Hazard statements
302 · H302-H315-H410
Precautionary statements
273 · P273-P301+P312+P330-P302+P352
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn,N
Risk Statements
22 · 22-38-50/53
Safety Statements
37 · 37-60-61
RIDADR
3077 · UN3077 9/PG 3
WGK Germany
3 · 3
RTECS
5250000 · DB5250000
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Skin Irrit. 2
Hazardous Substances Data
80 · 80-33-1(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rabbit: 5660mg/kg

Toxicology

Interactions · 1 item

140 RATS WERE TREATED WITH 100 MG/KG ORAL OVEX, PAIRED WITH AN EQUAL NUMBER OF CONTROLS. TEN TREATED AND TEN CONTROL RATS WERE GIVEN A LETHAL DOSE OF PARATHION (100 MG/KG, ORAL) AT DESIGNATED TIMES AFTER OVEX AND THE LENGTH OF SURVIVAL RECORDED. OVEX PRETREATMENT APPEARED TO PROVIDE MORE PROTECTION AGAINST PARATHION THAN PARAOXON TOXICITY. IT INCR THE RATE OF PARATHION METAB BY WHOLE LIVER HOMOGENATES BUT HAD ONLY A MARGINAL EFFECT ON THE RATE OF METAB OF PARAOXON.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 17,000(SRC), determined from a structure estimation method(2), indicates that chlorfenson will be immobile in soil(SRC). Volatilization of chlorfenson will not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.6X10-7 atm-cu m/mole(SRC), using a recommended regression equation(3), or from dry soil surfaces(SRC), based on an estimated vapor pressure of 1.9X10-6 mm Hg(SRC), determined from a fragment constant method(4).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 17,000(SRC), determined from a structure estimation method(2), indicates that chlorfenson should adsorb to suspended solids and sediment in the water(SRC). Chlorfenson is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 1.6X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). An estimated BCF value of 930(1,SRC), from an estimated log Kow(4,SRC), suggests that chlorfenson will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorfenson, which has an estimated vapor pressure of 1.9X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase chlorfenson is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 2 to 3 days(3,SRC). Particulate-phase chlorfenson may be physically removed from the air by dry deposition(SRC).

Food Survey Values · 1 item

Chlorfenson was detected in ready-to-eat composite food samples collected from 30 markets in 24 different cities during 1964-1968; only 1 composite sample, from fruit, contained chlorfenson at a concentration of 0.003 ppm(1). Chlorfenson was detected at unreported concentrations during the 1978-1982(4), 1989(2), 1990(3) regulatory and incidence/level monitoring of foods for pesticides. One sample of leaf and stem vegetables contained chlorfenson during the 1973 Total Diet study(5). Chlorfenson was measured in lemon rind following application(6).

Adverse EffectsOther Poison - Organochlorine
Acute Toxicity LinkChemical: OVEX
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for chlorfenson can be estimated to be about 17,000(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that chlorfenson will be immobile in soil(SRC).

Human Toxicity Excerpts · 2 items

... Human injury that may have been related to chlorfenson is ... a tendency to gastritis /which was found in/ 84 of 533 outpatients and in 86 of 104 inpatients, all of whom worked in the production of DDT, BHC, and chlorfenson.

... Highly positive reactions to patch tests with chlorfenson /were reported/ among farmers, greenhouse workers, and others with dermatitis attributed to pesticides.

Artificial Pollution SourcesIf chlorfenson is used as an insecticide and acaricide(1), it will be directly released to the environment(SRC).
Sediment/Soil ConcentrationsChlorfenson was detected in 1 of 1486 cropland soil samples at a concentration of 1.13 ppm during the National Soils Monitoring Program in 1971(1).
Environmental Bioconcentration · 1 item

An estimated BCF value of 930 was calculated for chlorfenson(SRC), using an estimated log Kow of 4.21(1,SRC) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will occur(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for chlorfenson is estimated as 1.6X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value suggests that chlorfenson will be essentially nonvolatile from water surfaces(2,SRC). However, the volatilization rate for chlorfenson was measured in static distilled water as 0.01 /day, giving a half-life of 69 days(4). Chlorfenson's values for vapor pressure, 1.9X10-6 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil surfaces, respectively, should not occur(SRC).

Non-Human Toxicity Excerpts · 5 items

AN ACARICIDE OF MODERATELY LOW ORAL TOXICITY IN LABORATORY ANIMALS. KIDNEY...DAMAGE IN THE RAT DURING CHRONIC EXPOSURES.

Definite toxic effects consisting of resp difficulty and spasms were evident at 2000 mg/kg /in BDF1 mice, oral/. When fed to rats for 90 days at...3000 ppm, chlorfenson caused significant retardation of growth, incr in liver size, incr in thyroid size, and characteristic histologic changes in the liver and thyroid, all in both males and females. Except for body growth in males, similar but lesser changes were produced by 1000 ppm. ... In some acutely poisoned mice, the only change noted was hemorrhage of the spleen.

The in vitro inhibition of deamination of biogenic amine substrates by rat brain monoamine oxidase (MAO) was /conducted/ with 61 insecticides, acaricides, and related cmpd. Twenty eight of these cmpd (6 organophosphates, 4 carbamates, 8 formamidines and 3 sulfonates) gave over 50% inhibition of the deamination of at least one substrate at assay levels of 0.001 M. Potasan was the most potent organophosphate MAO inhibitor and carbaryl was the most potent carbamate MAO inhibitor. Chlordimeform competitive inhibition values were slightly less than those of its N-desmethyl derivative. The most potent inhibitor of serotonin and dopamine deamination was ovex (chlorfenson) with pI50 values of 6.15 and 5.90, respectively.

Chlorfenson was nonmutagenic in the bacterial reversion-assay systems with 5 strains (TA100, TA98, TA1535, TA1537 and TA1538) of Salmonella typhimurium and Escherichia coli strain (WP2 hcr).

For more Non-Human Toxicity Excerpts (Complete) data for CHLORFENSON (6 total), please visit the HSDB record page.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
DB5250000
ridadr
UN3077 9/PG 3
Toxicity
LD50 oral in rabbit: 5660mg/kg
risk_code
22-38-50/53
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
hazard_code
Xn,N
safety_code
37-60-61
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H410
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Skin Irrit. 2
Precautionary statements
P273-P301+P312+P330-P302+P352
Hazardous Substances Data
80-33-1(Hazardous Substances Data)

...MAY BE USED AS DUSTS OR SPRAYS, &...OFTEN COMBINED WITH OTHER INSECTICIDE APPLICATIONS OR IN INSECTICIDE FUNGICIDE APPLICATIONS.

Combinations: Fac Super (with prothoate)

Use ClassificationACARICIDES
General Manufacturing Information · 4 items

...COMPATIBLE WITH ALL COMMONLY-USED SPRAY MATERIALS. HIGHLY TOXIC TO EGGS OF MANY PHYTOPHAGOUS MITES, WITH PRONOUNCED RESIDUAL OVICIDAL ACTION...OF LITTLE INSECTICIDAL ACTIVITY. GENERALLY NON-PHYTOTOXIC; SUSPECTED INJURY TO RASPBERRY. MAY BE USED TO SUPPRESS GROWTH OF ANNUAL GRASSES IN ESTABLISHED TURF; US PATENT 2,744,819.

MOST EFFECTIVE AS AN OVICIDE BUT ALSO TOXIC TO ACTIVE STAGES OF SPIDER MITES; LONG RESIDUAL EFFECT ALONG WITH LOW TOXICITY TO WARM-BLOODED ANIMALS AND INSECT POLLINATORS.

P-CHLOROPHENYL P-CHLOROBENZENESULFONATE IS EFFECTIVE IN CONTROLLING FLAGELLATES OF RED TIDE. THE MIN INHIBITORY CONCN AGAINST SEVERAL FLAGELLATE SPECIES WAS 0.1-30.0 PPM.

... Protected by US Patent 2528310. It is effective against mites of citrus and other fruit, vegetable crops and ornamentals at 17-32 g ai/100 l.

Applications · 3 items

DescriptionChlorfenson is an obsolete insecticide. It has a low aqueous solubility and a low volatility. Data on its persistence in soil and water systems is missing. It has a low mammalian oral toxicity and thought to be a skin irritant. data on ecotoxicology is scant but it does appear to have a low toxicity to birds and a moderate toxicity to fish.

UsesMiticide; control of powdery mildew.

General DescriptionChlorfenson is a pyrethroid pesticide effective against mites of citrus fruit, vegetable crops and ornamentals. It is a non-systemic acaricide with residual ovicidal activity.

Upstream & downstream products

Upstream raw materials

Ferric chlorideChlorosulfonic acid4-Chlorobenzenesulfonyl chlorideBenzenesulfonic acid,4-chloro-, phenyl ester4-Chlorophenol sodium saltSodium 4-chlorobenzene sulfinate4-Chlorophenol

Downstream products

Hexythiazox

Additional notes

DefinitionChEBI: Chlorfenson is an arenesulfonic acid.