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Dienochlor

Dienochlor structure

Dienochlor 

structure
  • CAS No:

    2227-17-0

  • Formula:

    C10Cl10

  • Chemical Name:

    Dienochlor

  • Synonyms:

    Bi-2,4-cyclopentadien-1-yl,1,1′,2,2′,3,3′,4,4′,5,5′-decachloro-;Bi-2,4-cyclopentadien-1-yl,decachloro-;1,1′,2,2′,3,3′,4,4′,5,5′-Decachlorobi-2,4-cyclopentadien-1-yl;HRS 16;HRS 16A;HRS 1654;Bis(pentachloro-2,4-cyclopentadien-1-yl);Hooker HRS 16;Hooker HRS 1654;Pentac WP;Decachlor;Pentac;Pentac SP;Decachlorobi-2,4-cyclopentadien-1-yl;Dienochlor;Pentac AquaFlow;NSC 26106;NSC 41880;1,2,3,4,5-Pentachloro-5-(1,2,3,4,5-pentachlorocyclopenta-2,4-dien-1-yl)cyclopenta-1,3-diene

Description

Dienochlor is an organochlorine compound.

Dienochlor Basic Attributes

474.61

474.64

218-763-5

243Z2SVZ40

41880|26106

DTXSID9032371

Tan crystalline solid|Yellow prisms from petroleum ether

2903890090

Characteristics

0

3.23 at 25 deg C

1.94g/cm3

122-123 °C

250 deg C (decomposes)

229.7ºC

1.662

In water, 2.50X10-2 mg/L @ 20 deg C

Store in original container in a dry place separate from reducing agents.

2.9 x 10 -4 Pa (25 °C)

Acute oral LD50 for male albino rats >3.16 g/kg, bobwhite quail 705 mg/kg (Worthing and Hance, 1991).

Henry's Law constant = 5.46X10-5 atm-cu m/mol at 25 °C /Estimated/

... light yellow powder, sometimes with faint onion or garlic odor. MP: 111-128 °C; Specific gravity/density: 1.923 (25 °C); Solubility: in iso-octane 7.89, toluene 59.00, acetonitrile 1.16, n-octanol 4.77, tetrahydrofuran 98.32 (all in g tech./100 ml); Stability: deinochlor was stable when stored at 54 °C for 14 d, and at 42 °C for 2 yr /Technical formulation/|Hydroxyl radical reaction rate constant = 7.86X10-13 cu-cm/molecule sec at 25 °C /Estimated/|... Dienochlor reacts rapidly with 1.0 mM GSH in phosphate buffer (pH 7.4) at 37 degrees C (t1/2 approximately 11 min) yielding a series of more than a dozen adducts.

Non-corrosive under dry conditions

Safety Information

6.1(a)

UN 2761

3

22

S22;S24

DT8225000

Xn: Harmful;

Technical dienochlor was stable when stored at 54 deg C for 14 days, and at 42 deg C for 2 yr. /Technical dienochlor/

P301 + P312 + P330

H302-H410

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.|Dispose of empty package in accordance with local, state, or federal regulations. Do not contaminate food, feed, ponds, lakes, waterways including sewers and domestic water supplies.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P391, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H320: Causes eye irritation [Warning Serious eye damage/eye irritation]|P264, P305+P351+P338, and P337+P313

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: 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/

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/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organochlorine pesticide, liquid/|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./ Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organochlorine pesticide, liquid/

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 eye contact, inhalation of spray mist. Wash thoroughly after handling. ... Do not reuse empty package. Triple rinse and empty flushings into spray tank.|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/|Personnel protection: Void breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organochlorine pesticide, liquid/|For more Preventive Measures (Complete) data for PENTAC (6 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 eye irritation.

Toxicity

LD50 Rat oral 3160 mg/kg|LD50 Rabbit percutaneous >3160 mg/kg, albino

3.31e+04 L/kg

Drug Information

In varying degrees, organochlorines are absorbed from the gut and also by the lung and across the skin. /Soild Organochlorines/|Within four days of receiving a single oral dose (1 mg/kg) of U-ring-(14)C dienochlor [bis(pentachloro-2,4-cyclopentadien-1-yl)] female rats excreted 2 and 88% of the applied (14)C in urine and feces, respectively. Metabolites could not be identified and the preponderance of the fecal radioactivity consisted of unextractable (14)C labeled residues. Within 1 day virtually all of the dienochlor had been degraded by rats, with only traces of parent dienochlor in excreta and tissues. After four days only 2% of the applied dose remained in tissues (mainly kidney, liver, and gastrointestinal tract). Pharmacokinetic studies with blood plasma and bile showed dienochlor (and/or its metabolites) to be poorly absorbed. Rats were exposed dermally for 24 hr to (14)C dienochlor formulated as Pentac WP miticide both as an aqueous suspension and as an undiluted wettable powder. Half of the dose adhered to the skin and the other half was found in gauze patches used to protect the treated skin. After a 24 hr exposure over 60% of the radiolabel that adhered to skin was removed by washing with an aqueous soap solution and 86% of this rinsing solution was unmetabolized dienochlor. The dienochlor and its metabolites were transported inefficiently from the application site; only 1% of the applied dose was detected in urine plus feces and less than or equal to 0.2% in tissues. With application rates that simulate field exposure by humans, the actual residue of dienochlor and metabolites in skin (eg, not removable by washing) is about thirteen times higher following exposure to dienochlor as undiluted wettable powder than as an aqueous suspension.

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/|In patients who have been poisoned by organochlorine contamination of skin, clothing, hair and/or eyes, decontamination must proceed concurrently with whatever resuscitative and anticonvulsive measures are necessary to preserve life. Contamination of the eyes should be removed by flushing with copious amounts of clean water. If the pesticide-exposed person remains alert and physically able, a prompt shower and shampoo may be appropriate, provided the patient is carefully observed to insure against sudden appearance of poisoning. If there are any indications of weakness, ataxia, or other neurologic impairment, clothing should be removed and a complete bath and shampoo given while the victim is recumbent, using copious amounts of soap and water. Attendants should wear rubber gloves. Surgical green soap is excellent for this purpose, but ordinary soap is about as good. The possibility of pesticide sequestered under fingernails or in skin folds should not be overlooked. Contaminated clothing should be promptly bagged and not returned until it has been thoroughly laundered. Contaminated leather shoes should be discarded. The possibility that pesticide has contaminated the inside surfaces of gloves, boots, and headgear should be considered. /Solid organochlorine insecticides/|If organochlorine has been ingested in a quantity sufficient to cause poisoning, the stomach and intestine must be emptied, and measures taken to limit toxicant absorption. Because seizure activity may develop rapidly, lavage, with a large bore orogastric tube and with rigorous protection of the airway, is probably preferable... . If the victim is convulsing, it is almost always necessary first to control seizures before attempting gastric intubation. The effectiveness of lavage in removing pesticide from the stomach diminishes rapidly with the passage of time. Particularly in poisoning by large doses of organochlorine, monitor pulmonary ventilation carefully to forestall respiratory failure. Assist pulmonary ventilation mechanically with oxygen whenever respiration is depressed. /Solid organochlorine insecticides/|For more Antidote and Emergency Treatment (Complete) data for PENTAC (6 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ Not a human skin primary irritant or sensitizer.|/CASE REPORTS/ Sensitivity to benomyl was observed in three patients, and to Captan, Delan (Dithionone), and Pentac in two of the patients.|/BIOMONITORING/ ... The SCE frequency was elevated in nonsmoking, but not in currently smoking sprayers when compared with the referents. There was a slight tendency towards an increased SCE frequency with decreasing degree of protection during pesticide applications. The frequency of pesticide applications, lifetime pesticide exposure, and in season plasma-cholinesterase inhibition (as an estimate of current exposure to organophosphates and carbamates) did not influence the SCE frequency or any of the hematological parameters.

decachlorobi-2,4-cyclopentadien-1-yl

Dienochlor Use and Manufacturing

Methods of Manufacturing

Dienochlor is produced by the catalytic reduction of hexachlorocyclopentadiene.

Uses

Miticide. Acaricide used for control of mites on ornamentals. Dienochlor is used for the control of mites (Tetrunychus spp., Panonychus ulmi and Polyphagotarsonemus latus) on roses, Chrysanthemums and other ornamentals.

Pentac wp; wettable powder (500 g ai/kg).|Pentac aquaflow (a 4-pound active/gallon water-base flowable)|Flowable|PENTAC WP|For more Formulations/Preparations (Complete) data for PENTAC (11 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Dienochlor (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.|Very low phytotoxicity of formulations /and/ lack of mite resistance to pentac after nearly 20 years of use.

PRODUCT ANALYSIS IS BY INFRARED SPECTROSCOPY @ 7.98 UM.|Analysis of products: ... By determination of total chlorine by the Stepanov method. Analysis of residues: by GLC with ECD.

Agrochemicals -> Acaricides

Computed Properties

Molecular Weight:474.6
XLogP3:6.3
Rotatable Bond Count:1
Exact Mass:473.682627
Monoisotopic Mass:469.688527
Heavy Atom Count:20
Complexity:530
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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