ENDRIN

Chemical properties

Endrin is an organochlorine compound. Endrin appears as a white or beige crystalline solid and is stable. It is incompatible with strong acids and strong oxidisers and corrodes some metals. Endrin decomposes on heating above 245°C, producing hydrogen chloride and phosgene. Endrin is incompatible with strong oxidisers, strong acids, and parathion and emits hydrogen chloride and phosgene when heated or burned.

Chemical properties

Endrin is an organochlorine compound. Endrin appears as a stable, white or beige crystalline solid. It is incompatible with strong acids and strong oxidizers and corrodes some metals.Endrin decomposes on heating above 245°C producing hydrogen chloride, phosgene. In fact, the US EPA has sharply restricted the availability and uses of many organochlorine groups of pesticides. These include DDT, aldrin, dieldrin, endrin, heptachlor, mirex, chlordecone, and chlordane, while many other organochlorines, however, remain the active ingredients of various home and garden products and some agricultural, structural, and environmental pest control products.

Chemical properties

Endrin is the common name of one member of the cyclodiene group of pesticides. It is a cyclic hydrocarbon having a chlorine-substituted, methano-bridge structure. Endrin is a white, crystalline solid

Physical properties

White, crystalline solid when pure; light tan color with faint chemical odor for technical grades. Odor threshold concentrations in air ranged from 18 to 41 ppb (quoted, Keith and Walters, 1992). Robeck et al. (1965) reported an odor threshold concentration of 9 ppb.

The Uses of ENDRIN

All uses of endrin in the United States were canceled by the manufacturer in 1986; formerly used as an insecticide, avicide, and rodenticide

The Uses of ENDRIN

Formerly as insecticide.

Definition

A stereoisomer of dieldrin which is the endo, exo isomer.

General Description

ENDRIN is a white crystalline, odorless solid dissolved in a liquid carrier. ENDRIN is water emulsifiable. ENDRIN is toxic by inhalation, skin absorption, and/or ingestion. When heated or burned ENDRIN may emit toxic hydrogen chloride and phosgene. ENDRIN is used as a pesticide.

Reactivity Profile

While a mixture of parathion and ENDRIN was being blended into a petroleum solvent, an exothermic reaction occurred that caused some of the petroleum solvent to vaporize. The solvent-vapor-air mixture exploded. The mechanical agitation possibly initiated the exothermic reaction, Doyle(1973). Toxic hydrogen chloride and phosgene may be generated when solution burns. Avoid strong oxidizers, strong acids and parathion. [EPA, 1998].

Hazard

Toxic by inhalation and skin absorption, use may be restricted. Headache, liver damage, and central nervous system impairment. Questionable carcinogen.

Health Hazard

ENDRIN is extremely toxic. It is rapidly absorbed through the skin. Symptoms appear between 20 minutes and 12 hours after exposure. There is evidence that ENDRIN may cause chromosomal damage. Doses of 1 mg/kg can cause symptoms. It is a suspected carcinogen. Also, it is a central nervous system depressant and hepatotoxin. Pregnant women are considered to be at special risk.

Health Hazard

Exposures to endrin cause toxicity and adverse health effects. Endrin is highly toxic to humans and species of animal. The symptoms of poisoning include, but are not limited to, headache, dizziness, nausea, vomiting, incoordination, tremor, mental confusion, and hyperexcitable state. Exposures to very high concentrations of endrin and in severe cases of poisoning, symptoms include convulsions, seizures, coma, and respiratory depression. In severe organochlorine compound poisoning, symptoms include myoclonic jerking movements, generalized tonic-clonic convulsions, respiratory depression following the seizures, and coma.

Health Hazard

Extremely toxic to experimental animals byall routes of exposure; also, highly toxic tohumans and animals by ingestion or skinabsorption; toxic effects similar to those ofaldrin and dieldrin; symptoms — headache,dizziness, nausea, vomiting, abdominal pain,insomnia, confusion, stupor, convulsions,tremors, rise in blood pressure, fever, frothing of mouth, deafness, coma, and respiratoryfailure; stimulant to central nervous system;ingestion of 50–60 mg can produce toxicsymptoms in human; can produce adversereproductive effects; a teratogenic substance;evidence of carcinogenicity in experimental animals and humans inadequate; oralLD50 value (mice): ～13 mg/kg, (guinea pig):16 mg/kg; U.S. EPA listed extremely hazardous substance; exposure limit: PEL/TLV TWA(skin) 0.1 mg/kg (OSHA, ACGIH).

Fire Hazard

Toxic hydrogen chloride and phosgene may be generated when solution burns. Avoid strong oxidizers, strong acids and parathion.

Agricultural Uses

Insecticide, Avicide: Not approved for use in EU countries. A U.S. EPA restricted Use Pesticide (RUP). It is a persistent and acutely toxic insecticide. Endrin is an insecticide which has been used to control insects, rodents, and birds, mainly on field crops such as cotton, maize, sugarcane, rice, cereals, ornamentals, and other crops. It has also been used for grasshoppers in non-cropland and to control voles and mice in orchards. Once widely used in the U.S., most uses were canceled in 1980 and it has not been produced nor sold in the U.S. since 1986. It is not easily dissolved in water and can remain in the soil for more than 14 years.

Trade name

COMPOUND 269®; EN 57®; ENDREX®; ENDRICOL®; ENDRIN CHLORINATED HYDROCARBON INSECTICIDE®; HEXADRIN®; MENDRIN®; NENDRIN®; OKTANEX®

Safety Profile

Poison by ingestion, skin contact, and intravenous routes. Experimental teratogenic and reproductive effects. Questionable carcinogen. Mutation data reported. A central nervous system stimulant. Highly toxic to birds, fish, and humans. Many cases of fatal poisoning have been attributed to it. Does not accumulate in human tissue. In humans, ingestion of 1 mg/kg has caused symptoms. A dangerous fire hazard. Mixtures with parahon dlssolve very exothermically in petroleum solvents and may cause an air-vapor explosion. See also ALDFUN.

Potential Exposure

A potential danger to those involved in manufacture, formulation and field application of this insecticide, avicide, and rodenticide. Pesticide not in use; TRI and/ or IUR indicates importers or manufacturers are unlikely.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contactsthe skin, remove contaminated clothing and wash immediately with soap and water. Speed in removing materialfrom skin is of extreme importance. Shampoo hairpromptly if contaminated. Seek medical attention immediately. If this chemical has been inhaled, remove fromexposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing hasstopped and CPR if heart action has stopped. Transferpromptly to a medical facility. When this chemical hasbeen swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit

Environmental Fate

Biological. In four successive 7-day incubation periods, endrin (5 and 10 mg/L) was recalcitrant to degradation in a settled domestic wastewater inoculum (Tabak et al., 1981). Soil. Microbial degradation of endrin in soil formed several ketones and aldehydes of which keto-endrin was the only metabolite identified (Kearney and Kaufman, 1976). In eight Indian rice soils, endrin degraded rapidly to low concentrations after 55 days. Degradation was highest in a pokkali soil and lowest in a sandy soil (Gowda and Sethunathan, 1976).
Under laboratory conditions, endrin degraded to other compounds in a variety of soils maintained at 45°C. Except for Rutledge sand, endrin disappeared or was transformed in the following soils after 24 hours: Lynchburg loamy sand, Magnolia sandy loam, Magnolia sandy clay loam, Greenville sandy clay and Susquehanna sandy clay. No products were identified (Bowman et al., 1965).
The disappearance half-lives for endrin in field soils under flooded and nonflooded conditions were 130 and 468 days, respectively (Guenzi et al., 1971). The average disappearance half-life in flooded soils under laboratory conditions was 31 days (Gowda and Sethunathan, 1976, 1977).
The percentage of endrin remaining in a Congaree sandy loam soil after 14 years was 41% (Nash and Woolson, 1967).
Groundwater. According to the U.S. EPA (1986) endrin has a high potential to leach to groundwater.
Plant. In plants, endrin is converted to the corresponding sulfate (Hartley and Kidd, 1987).
Surface Water. Algae isolated from a stagnant fish pond degraded 24.4% of the applied endrin to ketoendrin (Patil et al., 1972).
Photolytic. Photolysis of thin films of solid endrin using UV light (l = 254 nm) produced d-ketoendrin, endrin aldehyde and other compounds (Rosen et al., 1966). Endrin exposed to a hot California sun for 17 days completely isomerized to d-ketoendrin or 1,8- exo-9,10,11,11-hexachlorocyclo[6.2.1.13,6.02,7.04,10]dodecan-5-one (Burton and Pollard, 1974). Irradiation of endrin by UV light (l = 253.7 nm and 300 nm) or by natural sunlight in cyclohexane and n-hexane solution resulted in an 80% yield of 1,8-exo-9,11,11-pentachloropentacyclo[ 6.2.1.13,6.02,7.04,10]dodecan-5-one (Zabik et al., 1971). When an aqueous solution containing endrin was photooxidized by UV light at 90–95°C, 25, 50 and 75% degraded to carbon dioxide after 15.0, 41.0 and 172.0 hours, respectively (Knoevenagel and Himmelreich, 1976).
Chemical/Physical. At 230°C, endrin isomerizes to an aldehyde and a ketone. When heated to decomposition, hydrogen chloride and phosgene may be released (NIOSH, 1994) but residues containing an aldehyde (15–20%), a ketone (55–60%), a caged alcohol (5%), and other volatile products (15–20%) were reported (Phillips et al., 1962).
In water, endrin will undergo nucleophilic attack at the epoxide moiety forming endrin diol (Kollig, 1993).
At 50°C, endrin was not unaffected by the oxidants chlorine, permanganate and persulfate (Leigh, 1969).

Solubility in organics

At 25 °C: acetone (170 g/L), benzene (138 g/L), carbon tetrachloride (33 g/L), hexane (71 g/L), xylene (183 g/L) (Windholz et al., 1983). Soluble in aromatic hydrocarbons, esters, and ketones (ITII, 1986).

Solubility in water

At 25 °C: acetone (170 g/L), benzene (138 g/L), carbon tetrachloride (33 g/L), hexane (71 g/L), xylene (183 g/L) (Windholz et al., 1983). Soluble in aromatic hydrocarbons, esters, and ketones (ITII, 1986).

Shipping

UN2761 Organochlorine pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials

Toxicity evaluation

Endrin (40) is 1,2,3,4,10,10-hexachloro- 1,4,4a,5,8,8a-hexahydro-6,7-epoxy-1,4-endo,endo- 5,8-dimethanonaphthalene (mp 245 dec, vp 0.022 mPa at 25 ?C) and is soluble in water to 23 μg/L. This compound is the endo,endo isomer of dieldrin, which is less stable and more toxic than dieldrin with rat LD₅₀ values of 17.8 and 7.5 (oral) and 15 (dermal) mg/kg. It was used as a cotton insecticide, but because of its high toxicity to fish, its use was restricted.

Incompatibilities

Incompatible with strong oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids (forms explosive vapors), oxoacids, epoxides, and parathion. Slightly corrosive to metal

Waste Disposal

A disposal procedure recommended by the manufacturer consists of absorption, if necessary, and burial at least 18 in deep; preferably in sandy soil in a flat or depressed location away from wells, livestock, children, wildlife, etc. Incineration is the recommended method. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

Precautions

Students and occupational workers should be careful during handling of endrin. Workers should not wash away the chemical waste into the sewer, but sweep spilled chemical substance into sealable containers. Workers should use extra personal protection, face shield and eye protection, a chemical protection suit, and self-contained breathing apparatus. Exposures to endrin cause effects on the CNS leading