Encyclopedia / Pharmaceutical Intermediates

OVEX

CAS：80-33-1
MW:303.16112
MF：C12H8Cl2O3S

Miticide; control of powdery mildew. OVEX Preparation Products And Raw materials Preparation Products View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data

1. Names and Identifiers

1.1 Name: OVEX

1.2 Synonyms: (4-Chloor-fenyl)-4-chloor-benzeen-sulfonaat; (4-chlorophenyl) 4-chlorobenzenesulfonate; (4-Chlor-phenyl)-4-chlor-benzol-sulfonate; (4-Cloro-fenil)-4-cloro-venzol-solfonato; 4-Chlorobenzenesulfonate de 4-chlorophenyle; 4-chlorobenzenesulfonatede4-chlorophenyle; 4-chlorobenzenesulfonatede4-chlorophenyle(french); 4-chlorobenzenesulfonatede4-chlorphenyle(french); 4-chloro-benzenesulfonicaci4-chlorophenylester; 4-chlorophenyl 4-chlorobenzene-1-sulfonate; 4-chlorophenyl 4-chlorobenzenesulfonate; 4-chlorophenyl-4-chlorobenzenesulfonate; Benzolsulfonate; Chlorfensin; Chlorofenizon; chlorofenson; chlorofensone; Difenson; EINECS 201-270-4; ephirsulfonate; Ephirsulphonate; Ethersulfonate; MFCD00055266; Niagaratran; ovatron; p-chlorophenyl p-chlorobenzenesulfonate;

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1.3 CAS No.: 80-33-1

1.4 CID: 6635

1.5 EINECS: 201-270-4

1.6 Molecular Formula: C12H8Cl2O3S

1.7 Inchi: 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

1.8 InChkey: RZXLPPRPEOUENN-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=CC=C1OS(=O)(=O)C2=CC=C(C=C2)Cl)Cl

1.10 Isomers Smiles: C1=CC(=CC=C1OS(=O)(=O)C2=CC=C(C=C2)Cl)Cl

2. Properties

2.1 Appearance: Crystalline

2.2 Color/Form: CRYSTALS FROM BENZENE|White, crystalline solid

2.3 Corrosivity: Noncorrosive

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

2.5 Spectral Properties: SADTLER REFERENCE NUMBER: 34349 (IR, PRISM); 12335 (IR, GRATING); MAX ABSORPTION (ALCOHOL): 230 NM (LOG E= 4.27); 266 NM (LOG E= 3.05); 269 NM (LOG E= 3.04); 277 NM (LOG E= 2.91)
Intense mass spectral peaks: 111 m/z (100%), 175 m/z (75%), 75 m/z (53%), 99 m/z (51%)
IR: 3171 (Coblentz Society Spectral Collection)
UV: 14458 (Sadtler Research Laboratories Spectral Collection)
MASS: 4824 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)

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2.6 Stability: HYDROLYZES IN ALKALI

2.7 StorageTemp: 0-6°C

3. Use and Manufacturing

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

3.2 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.

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3.3 Usage: Miticide; control of powdery mildew. OVEX Preparation Products And Raw materials Preparation Products

4. Safety and Handling

4.1 DisposalMethods: 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.

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4.2 Formulations/Preparations: 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)

4.3 Protective Equipment and Clothing: CAUSES SKIN IRRITATION IN MAN...

4.4 Skin, Eye, and Respiratory Irritations: CAUSES SKIN IRRITATION IN MAN...

4.5 Safety: Moderately toxic by ingestion and possibly other routes. Questionable carcinogen with experimental tumorigenic data. A pesticide. When heated to decomposition it emits very toxic fumes of Cl⁻ and SO_x. See also SULFONATES and CHLORINATED HYDROCARBONS, AROMATIC.
Hazard Codes: Xn, N
Risk Statements: 22-38-50/53
R22: Harmful if swallowed
R38: Irritating to skin
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 37-60-61
S37: Wear suitable gloves
S60: This material and its container must be disposed of as hazardous waste
S61: Avoid release to the environment. Refer to special instructions / safety data sheets
RIDADR: UN3077 9/PG 3
RTECS: DB5250000

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4.6 Specification: 4-Chlorophenyl-4-chlorobenzene sulfonate (CAS NO.80-33-1) is also called Ovotox(r) ; Ovex ; p-Chlorophenyl-p-chlorobenzene sulfonate ; Orthotran(r) ; Mitran(r) ; (4-Chloor-fenyl)-4-chloor-benzeen-sulfonaat . 4-Chlorophenyl-4-chlorobenzene sulfonate (CAS NO.80-33-1) is chemical stability. But it decomposits when encountered alkali. 4-Chlorophenyl-4-chlorobenzene sulfonate (CAS NO.80-33-1) is moderate toxic.It will produce toxic chloride and sulfur oxide gases when buring. So the storage environment should be ventilate, low-temperature and dry.Keep it separate from raw materials of food.

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

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Synthesis Route

80-33-1Total: 3 Synthesis Route

2437-33-4

80-33-1 11 Suppliers

106-48-9 191 Suppliers

98-60-2 143 Suppliers

80-33-1 11 Suppliers

8. Precursor and Product

precursor:

1193-00-6

98-60-2

2437-33-4

106-48-9

product:

10504-90-2

10504-94-6

106-48-9

73842-46-3

98-66-8

2948-37-0

9. Computed Properties

Molecular Weight：303.16112g/mol
Molecular Formula：C₁₂H₈Cl₂O₃S
Compound Is Canonicalized：True
XLogP3-AA：301.9571207
Monoisotopic Mass：301.9571207
Complexity：350
Rotatable Bond Count：3
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：3
Topological Polar Surface Area：51.8
Heavy Atom Count：：18
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBwMABGAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAGgYAAAAACAaA0CAwB4AAAAKAACBCAHBCAEAgJQAIiBgGCogIJiKBExKAMAAkwBEIiAeAQAAAACIAAAAAAAAARAAAAAAAAAAAAAAAAA==

10.Other Information

BRN: 2944674

Uses: Miticide; control of powdery mildew.

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

用途: Chlorfenson is used to treat onychomycosis (nail fungus) as the primary indication.

Storage Conditions: 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.

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

Disposal Methods: 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.

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Special Reports: Toxicology Review: Residue Reviews 56: 107 (1975)

Interactions: 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.

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

Environmental Fate: 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).

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Abiotic Degradation: 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).

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Bioconcentration: 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).

Mobility: 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).

Volatilization: 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).

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Food Survey Values: 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).

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Metabolism: 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.

Human Toxicity Excerpts: ... 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.

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Mesh Entry Terms: 4-chlorophenyl 4-chlorobenzenesulfonate

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

Formulations: 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)

Manufacturing Info: ...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.

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