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Home > Encyclopedia > Chlorbenside

Chlorbenside

Chlorbenside structure

Chlorbenside 

structure
  • CAS No:

    103-17-3

  • Formula:

    C13H10Cl2S

  • Chemical Name:

    Chlorbenside

  • Synonyms:

    Benzene,1-chloro-4-[[(4-chlorophenyl)methyl]thio]-;Sulfide,p-chlorobenzyl p-chlorophenyl;1-Chloro-4-[[(4-chlorophenyl)methyl]thio]benzene;Chlorbenside;p-Chlorobenzyl p-chlorophenyl sulfide;p-Chlorobenzyl p-chlorophenyl sulphide;4-Chlorobenzyl 4-chlorophenyl sulphide;Chlorparacide;Chlorsulphacide;Mitox;Chlorbensid;Chloracide;CP 20;4-Chlorobenzyl 4-chlorophenyl sulfide;NSC 33078;1-Chloro-4-[(4-chlorophenyl)sulfanylmethyl]benzene

  • Categories:

    Analytical Chemistry  >  Standard

Description

Crystals; almond-like odor (technical grade).Insoluble in water; soluble in aromatic hydrocarbons, acetone. Resistant to acid and alkaline hydrolysis.Generic name for an agricultural toxicant.


Chlorobenside is an organic sulfide.

Chlorbenside Basic Attributes

269.19

269.19

203-084-9

FLR6R453DD

33078

DTXSID1041766

Crystals|Colorless

2930909090

Characteristics

25.3

5.42

1.4210 g/cm3 @ Temp: 25 °C

75-76 °C

83-84 °C @ Press: 2.4 x 10-3 Torr

168.4±22.3 °C

1.647

Less than 1:5000 in water

0-6°C

1.21X10-5 mm Hg at 30 deg C

Oral-Rat LD50: 2000mg/kg; unreported-mouse LD50: 3000 mg/kg

Combustion produces toxic sulfur oxides and chloride gases

Henry's Law constant = 6.96X10-6 atm-cu m/mol at 25 °C /Estimated/

Resistant to acid & alkaline hydrolysis; strong oxidizing agents convert it to corresponding sulfoxide and sulfone|May have almond-like odor /technical grades/|Hydroxyl radical reaction rate constant = 1.26X10-11 cu-cm/molecule sec at 25 °C /Estimated/

Non-corrosive

Safety Information

NONH for all modes of transport

3

22

S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes .

WQ2975000

Xn

Warehouse ventilated, low temperature and dry

P264, P270, P301+P312, P330, P501

H302

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|Organic Pesticides Disposal (except organic mercury, lead, cadmium, and arsenic compounds): Compounds should be disposed of in a pesticide incinerator at a temperature/dwell combination that will completely destroy the pesticide. Emissions from such incineration must meet the standards of the Clean Air Act of 1970; any liquids, sludges, or solid residues generated must be disposed of so as to meet Federal, State, and local pollution control requirements. (Municipal solid waste incinerators may be used for this procedure, if they meet all the necessary requirements and operations are supervised properly.) /Organic pesticide/|If incineration facilities are unavailable for a particular organic or metallo-organic pesticide (except organic mercury, lead, cadmium, and arsenic compounds), additional disposal methods include, soil injection, chemical degradation, burial (in a designated landfill), or well injection. However, persons considering the chemical degradation method should contact EPA's Regional Administrator ... prior to attempting disposal, while the well injection method should only be considered after all reasonable alternative measures have been explored and found to be less satisfactory in terms of environmental protection. If the above approved disposal methods are unavailable, temporary storage of organic and metallo-organic pesticides (except organic mercury, lead, cadmium and arsenic compounds), may be undertaken. /Organic or metallo-organic pesticide/|Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/|For more Disposal Methods (Complete) data for CHLORBENSIDE (6 total), please visit the HSDB record page.

Resistant to acid and alkaline hydrolysis. Strong oxidizing agents convert it to the corresponding sulfoxide and sulfone.

FAO/WHO; Evaluation of the Toxicity of Pesticide Residues in Food: Chlorbenside (1965). Available from: http://www.inchem.org/documents/jmpr/jmpmono/v065pr08.htm as of July 13, 2004.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory.

If the material is not on fire and not involved in a fire: Wear boots, protective gloves, and goggles. /Organochlorine pesticide, liquid, (compounds and preparations) (insecticides, other than agricultural, nec)/|Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. .... /Organochlorine pesticide, liquid; Organochlorine pesticide, solid, toxic/

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (material itself does not burn or burns with difficulty). Use water in flooding quantities as fog. Use "alcohol" foam, carbon dioxide, or dry chemical. Wear self-contained breathing apparatus when fighting fires involving this material. /Organochlorine pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticide, liquid/|If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticides, solid, toxic/

In case of damage to, or leaking from containers of the material, contact the pesticide safety team network. Telephone; (800) 424-9300. /Organochlorine pesticide, liquid (compounds and preparations) (insecticides, other than agricultural, nec)/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. /Organochlorine pesticide, solid, toxic/|Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. /Organochlorine pesticide, solid, toxic/|Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organochlorine pesticide, liquid/|For more Cleanup Methods (Complete) data for CHLORBENSIDE (6 total), please visit the HSDB record page.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|Avoid contact with eyes & skin. Do not inhale dust & spray mists.|If the material is not on fire and not involved in a fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock down vapors. Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages without protective equipment. /Organochlorine pesticide, liquid, (compounds and preparations) (insecticides, other than agricultural, nec)/|Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ...Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate chemical protective clothing. /Organochlorine pesticides, solid, toxic/|For more Preventive Measures (Complete) data for CHLORBENSIDE (7 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Slight irritant action on skin & eyes.

Toxicity

moderately toxic

LD50 Mouse oral >3000 mg/kg bw /from table/|LD50 Mouse oral >10,000 mg/kg bw /technical product; from table/|LD50 Rat oral >10,000 mg/kg bw /technical product; from table/|LD50 Rat oral 2000 mg/kg

/AQUATIC SPECIES/ ... Several moderately hydrophobic pesticides including DCPA or dacthal, chlorbenside, pentachlorophenol, and CDEC or sulfallate do inhibit dye efflux from gill cells indicating that they are substrates or inhibitors, but the more hydrophobic xenobiotics DDT, DDD, DDE, and Aroclor 1254 do not, indicating that they are not substrates.

Most organochlorine pesticides are efficiently absorbed from the gut and through the skin. /Organochlorines/

Drug Information

In varying degrees, organochlorines are absorbed from the gut and also by the lung and across the skin. /Soild Organochlorines/|After 13 weeks of feeding at a 10-ppm dose level there was no appreciable chlorbenside in any tissue of the rats except fat and possibly liver. At 100 ppm there were measurable concentrations in liver, kidney and fat but not in the blood or brain; whilst at 1000 ppm there were measurable concentrations in all organs, although the amount in the blood was barely detectable. The greatest amount of chlorbenside found in any one animal was 184 ug in a whole rat which had received the highest dose level of 1000 ppm. This was about one fiftieth of the daily intake. The total body load fell to about one sixth within 2 weeks of stopping treatment.|Rabbits were given chlorbenside orally in a dose of about 300 mg/kg body-weight and the excretion of sulfide (chlorbenside), sulfoxide and sulfone in urine and feces was followed. 97.4% of the dose was recovered unchanged from the feces, and traces of sulfoxide were present in the urine

In warm-blooded species, eliminated /in urine/ as a glucuronic acid conjugate.

In adequate dosage, /organochlorines/ interfere with axonic transmission of nerve impulses and, therefore, disrupt the function of the nervous system, principally that of the brain. This results in behavioral changes, sensory and equilibrium disturbances, involuntary muscle activity, and depression of vital centers, particularly those controlling respiration. /Organochlorines/

Treatment is symptomatic and supportive. Oils should not be used as either cathartics or dermal cleansing agents, as they increase absorption. Gastric lavage and use of activated charcoal and sodium sulfate are indicated for ingestion. If dermal exposure occurred, contaminated clothes should be removed, and the skin should be thoroughly cleansed with soap and water. Management of seizures in both children and adults is with Valium or phenobarbital. Respiratory depression and even respiratory arrest, especially with concomitant use of Valium and phenobarbital in children, may occur. These drugs preferably should be used only in critical care areas where emergency endotracheal intubation can be performed. /It is recommended/ that epinephrine not be utilized in patients with organochlorine poisoning, as the organochlorines induce myocardial irritability and ventricular arrhythmias may occur. However, dopamine may be necessary in the event of hypotension unresponsive to fluid administration, and epinephrine may be necessary in the event of cardiopulmonary arrest. /Organochlorine insecticides/|Persons exceptionally exposed to organochlorine pesticides by any route should be observed for sensory disturbances, incoordination, speech slurring, mental aberrations, and involuntary motor activity that would warn of imminent convulsions. If convulsions occur, place the victim in the left lateral decubitus position with the head down. Move away furniture or other solid objects that may be a source of injury. If jaw movements are violent, place padded tongue blades between the teeth to protect the tongue. Whenever possible, remove dentures and other removable dental work. Aspirate oral and pharyngeal secretions, and, when possible, insert an oropharyngeal airway to maintain an open passage unobstructed by the tongue. Minimize noise and any manipulation of the patient that may trigger seizure activity. Administer oxygen by mask. Maintain pulmonary gas exchange by mechanically assisted ventilation whenever respiration is depressed. /Solid organochlorine insecticides/

/SIGNS AND SYMPTOMS/ May be irritating to skin.|/OTHER TOXICITY INFORMATION/ Organochlorine pesticide can cause illness by inhalation, skin absorption, and/or ingestion. /Organochlorine pesticide, liquid, (compounds and preparations) (insecticides, other than agricultural, nec)/

chlorbenside

Chlorbenside Use and Manufacturing

Methods of Manufacturing

Chlorbenside is made by the reaction of p-chlorophenyl mercaptan and p-chlorobenzyl chloride.

Uses

Acaricide, especially for the control of eggs and larvae of red spider mites.

Production

1983 US production: 76,140,000 lb /Cyclic insecticides and rodenticides/

20% wettable powder; 20% miscible oil (emulsifiable concn); 10.6% vaporizing soln.|Grade: Technical|Elimite|Orthocide|For more Formulations/Preparations (Complete) data for CHLORBENSIDE (15 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Chlorbenside (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.|... Technical product contains about 90% p,p'-isomer, 5% o,p'-isomer, and 2.5% m,p'-isomer.|... Little insecticidal activity. ... Compatible with other plant-protection products in the appropriate types of formulation.

MICRO: (A) OXIDIZE TO SULFONE, NITRATE IN FUMING NITRIC-SULFURIC ACID TO TRINITRO COMPD WHICH, LIKE DDT, REACTS WITH SODIUM METHOXIDE IN BENZENE TO GIVE PURPLE COLOR. (B) OXIDIZE TO SULFONE WITH CR2O3 IN GLACIAL ACETIC ACID ... EXTRACT WITH ETHER, CONDENSE WITH M-DINITROBENZENE & MEASURE COLOR @ 510 NM. (C) EXTRACT USING MILLS-ONLEY-GAITHER PROCEDURE. CHLORBENSIDE & CHLORBENSIDE SULFOXIDE ARE CONVERTED TO CHLORBENSIDE SULFONE BY OXIDATION WITH CHROMIC-ACETIC ACID SOLN.

Computed Properties

Molecular Weight:269.2
XLogP3:5.2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:267.9880269
Monoisotopic Mass:267.9880269
Topological Polar Surface Area:25.3
Heavy Atom Count:16
Complexity:194
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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