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Home > Encyclopedia > Chlorfenson

Chlorfenson

Chlorfenson structure

Chlorfenson 

structure
  • CAS No:

    80-33-1

  • Formula:

    C12H8Cl2O3S

  • Chemical Name:

    Chlorfenson

  • Synonyms:

    Benzenesulfonic acid,4-chloro-,4-chlorophenyl ester;Benzenesulfonic acid,p-chloro-,p-chlorophenyl ester;D 854;C 1006;K 6451;Acaricydol E 20;Chlorfenson;p-Chlorophenyl p-chlorobenzenesulfonate;p-Chlorophenyl p-chlorobenzenesulphonate;CPCBS;Estonmite;Genite 883;Lethalaire G-58;Miticide K 101;Onex;Orthotran;Otracid;Ovex;Ovochlor;Ovotox;Ovotran;PCPCBS;4-Chlorophenyl 4-chlorobenzenesulfonate;4-Chlorophenyl 4-chlorobenzenesulphonate;CCS;Sappilan;Chlorofenizon;Ethersulfonate;Chlorbenzolsulfonat;Chlorfensin;Benzolsulfonat;Erysit;Roztoczol fluid;Ovatran;Danicut;NSC 5618;Ephirsulfonate

  • Categories:

    Cosmetic Ingredient  >  Antimicrobials

Description

Chlorfenson is an arenesulfonic acid.|Chlorfenson is developed by Moberg Derma for the treatment of onychomycosis (nail fungus) as the primary indication.

Chlorfenson Basic Attributes

303.16

303.16

201-270-4

LW65NJ3YWV

5618

DTXSID5020310

CRYSTALS FROM BENZENE|White, crystalline solid

Characteristics

51.8

4.84190

Crystalline

1.464g/cm3

86.5 °C

429.6ºC at 760 mmHg

213.6ºC

1.609

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

0-6°C

Negligible at 25 deg C

Oral-Rat LD50: 2000 mg/kg; Oral-Mouse LD50: 1475 mg/kg

Combustion produces toxic chloride and sulfur oxide gases

Noncorrosive

Safety Information

UN30779/PG3

3

22-38-50/53

37-60-61

DB5250000

Xn,N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

HYDROLYZES IN ALKALI

P273-P501

H302-H315-H410

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.

Toxicology Review: Residue Reviews 56: 107 (1975)

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P302+P352, P321, P330, P332+P313, P362, P391, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

CAUSES SKIN IRRITATION IN MAN...

Chlorfenson 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).

Toxicity

moderately toxic

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.

LD50 Mouse oral, male and female >4,000 mg/kg|LD50 Rat oral 2,000 mg/kg

If chlorfenson is used as an insecticide and acaricide(1), it will be directly released to the environment(SRC).

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).

The rate constant for the vapor-phase reaction of chlorfenson with photochemically produced hydroxyl radicals has been estimated as 6.6X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 2 to 3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). This compound does not adsorb in the visible range(2) and is not expected to photodegrade(SRC).

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).

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).

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).

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).

Drug Information

Investigated for use/treatment in fungal infections.

3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OUNCE & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

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.

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.

... 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.

4-chlorophenyl 4-chlorobenzenesulfonate

Chlorfenson Use and Manufacturing

Methods of Manufacturing

The first preparation method uses p-chlorobenzenesulfonic acid and chlorosulfonic acid as raw materials to synthesize acaricide through the following steps. The second preparation method uses p-chlorophenol and p-chlorobenzenesulfonyl chloride as raw materials to synthesize acaricide under alkaline conditions.

Uses

Miticide; control of powdery mildew.

Production

(1977) NOT PRODUCED COMMERCIALLY IN US|(1979) NOT PRODUCED COMMERCIALLY IN US

AS WETTABLE POWDERS (40% & 50%); EMULSIFIABLE CONCN; 5% & 10% DUSTS|...MAY BE USED AS DUSTS OR SPRAYS, &...OFTEN COMBINED WITH OTHER INSECTICIDE APPLICATIONS OR IN INSECTICIDE FUNGICIDE APPLICATIONS.|Combinations: Fac Super (with prothoate)

...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.

MACRO: CPAC METHOD, HYDROLYZE WITH METHANOLIC KOH & BACK TITRATE; FAO PLANT PROT BULL, 12, 3, 1964. MICRO: STRIP WITH BENZENE; HYDROLYZE WITH ALCOHOLIC KOH & CONVERT P-CHLOROPHENOL...WITH 4-AMINOANTIPYRINE IN PRESENCE OF POTASSIUM FERRICYANIDE ... . RESIDUE: EXTRACT WITH BENZENE, HYDROLYZE WITH ALCOHOLIC KOH TO YIELD P-CHLOROPHENOL, SEPARATE BY STEAM DISTILLATION & NITROSATE, SEPARATE BY COLUMN CHROMATOGRAPHY, ANALYZE @ 430 NM.|ANALYSIS FOR MULTIPLE RESIDUES OF ORGANOCHLORINE PESTICIDES IN FOODS AND FEED BY FLORISIL ELUTION CHROMATOGRAPHY PLUS GAS-LIQ CHROMATOGRAPHY IS DESCRIBED.|Retention ration data compiled by the FDA in its Pesticide Anal Manual (PAM) using packed gas chromatography columns were examined for usage when capillary gas chromatography was applied for residue analysis.|Method HERL_001. Modification of Mills, Onley, Gaither Method for the Determination of Multiple Organochlorine Pesticides and Metabolites in Human or Animal Adipose Tissue. GCECD method.|For more Analytic Laboratory Methods (Complete) data for CHLORFENSON (12 total), please visit the HSDB record page.

Agrochemicals -> Acaricides, Insecticides|ACARICIDES

Computed Properties

Molecular Weight:303.2
XLogP3:4.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:301.9571207
Monoisotopic Mass:301.9571207
Topological Polar Surface Area:51.8
Heavy Atom Count:18
Complexity:350
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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