Description
Lindane is one of eight different hexachlorocyclohexane
(HCH), [58-89-9], C6H6Cl6, isomers and
its Chemical Abstract name is 1α, 2α,3β,4α,5α,6β-
hexachlorocyclohexane 58-89-9 (γ-HCH or γ -BHC, benzene
hexachloride) (80). Commercial products containing
lindane are marketed as either a mixture of isomers
or as the pure γ -BHC isomer. Not unexpectedly, lindane
is a highly stable lipophilic compound and it has
been used extensively worldwide as an insecticide. In
contrast, hexachloropentadiene, [77-47-4], C5Cl6, is an
extremely reactive industrial intermediate used as a chemical
intermediate in the synthesis of a broad range of
cyclodiene-derived pesticides, which include endosulfan,
endrin, heptachlor, and several different organohalogen
flame retardants (81).
Chemical Properties
BHC is a white-to-brownish crystalline solid
with a musty, phosgene-like odor.
Chemical Properties
white powder
Chemical Properties
Lindane is a white to yellow, crystalline powder with a slight, musty odor (pure material is odorless).
Physical properties
Colorless to yellow crystalline solid with a slight, musty, chlorinated-like odor. Odor threshold
concentration is 12.0 mg/kg (Sigworth, 1964). Robeck et al. (1965) reported an odor threshold of
330 ppb.
Originator
Kwell,Reed Carnrick,US,1952
Uses
The only identified uses for hexachlorocyclohexane-containing products are based on the insecticidal activity of the γ isomer (lindane), which is considered to be the only insecticidally effective component (Extoxnet 1996). Lindane or technical-grade hexachlorocyclohexane containing the γ isomer is used primarily as an insecticide in the treatment of wood and wooden structures, seed grains, and livestock (ATSDR 2005, HSDB 2009). Other major uses are as an insecticide for several dozen fruit and vegetable crops, in baits and seed treatments for rodent control, and for treatment of scabies (mites) and lice. It is approved by the U.S. Food and Drug Administration foruse in three products for the treatment of lice and scabies (one lotionand two shampoos) (FDA 2009). Agricultural and pesticide uses accounted for about 270,000 kg (594,000 lb) of lindane and 450,000 kg (1 million pounds) of technical-grade hexachlorocyclohexane in 1974;the remaining uses were industrial or pharmaceutical (IARC 1979).
Uses
Pesticide and insecticide.
Indications
Lindane (Gamma benzene hexachloride, Kwell, Thionex) is a cyclic chlorinated
hydrocarbon originally developed as an agricultural insecticide. It is absorbed
through the chitinous exoskeleton and stimulates the nervous system, resulting in
seizures and death of the insect. It is both a pediculicide and scabicide, with a
45% to 70% ovicidal effect. Resistance has been shown to Pediculosis capitis and
Sarcoptes scabiei.
Lindane can be absorbed through intact skin following topical
application and has the potential for CNS toxicity. It should therefore be used with
great caution in infants, children <2 years of age, elderly patients, and pregnant
and lactating women. It may be irritating to the eyes or mucous membranes; hence,
these areas should be avoided. Irritant dermatitis may occur with use of excessive amounts or over prolonged periods. Toxicity, if overused, may result in nausea,
vomiting, seizures, or even bone marrow suppression.
Lindane is an organochlorine with very slow onset of action and poor ovicidal activity;
it takes over 3 hours to kill the lice during which increased lice crawling and
twitching can cause increased pruritus for the patient. Lindane is available as a
shampoo for the treatment of pediculosis capitis and/or pubis and in cream and
lotion form for treating scabies and all forms of pediculosis. GBH also repels
ticks and other arthropods and kills chiggers.
Definition
ChEBI: Beta-hexachlorocyclohexane is the beta-isomer of hexachlorocyclohexane. It has a role as a persistent organic pollutant. It is an organochlorine pesticide and a hexachlorocyclohexane.
Manufacturing Process
Chlorine gas was gradually passed into 660 parts of benzene contained in a
lead-lined reaction vessel until 890 parts of the gas had been absorbed. The
mixture was stirred continuously and the temperature maintained at 15°C to
20°C.
The supply of chlorine was then interrupted and the precipitated solid filtered
off and dried. In weight, it was found to be equivalent to 900 parts. The
mother liquid was then mixed with 330 parts of benzene and the mixture
again treated with 890 parts of chlorine in the manner described.
After filtering the reaction mixture resulting from the second chlorination, the
filtrate was again mixed with a smaller quantity of benzene and again
chlorinated in a similar manner. In this way, a continuous process for the
preparation of benzene hexachloride resulted.
That benzene hexachloride isomer mixture is then the raw material for lindane
production. The production of lindane per se is not a chemical synthesis
operation but a physical separation process. It is possible to influence the
gamma isomer content of benzene hexachloride to an extent during the
synthesis process. Basically, however, one is faced with the problem of
separating a 99%-plus purity gamma isomer from a crude product containing
perhaps 12 to 15% of the gamma isomer. The separation and concentration
process is done by a carefully controlled solvent extraction and crystallization
process. One such process is described by R.D. Donaldson et al. Another
description of hexachlorocyclohexane isomer separation is given by R.H.
Kimball.
brand name
Benhexachlor;Gamex;Gamma benzene;Hexachloride.
Therapeutic Function
Pediculicide, Scabicide
World Health Organization (WHO)
Lindane has been available for more than 25 years and is widely
used as an agricultural and household pesticide.
General Description
Colorless solid with a musty odor; pure material is odorless. Used as a pesticide and scabicide.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
LINDANE is incompatible with strong bases. LINDANE is incompatible with powdered metals such as iron, zinc and aluminum. LINDANE is also incompatible with oxidizing agents. LINDANE can undergo oxidation when in contact with ozone. When exposed to alkalis, LINDANE undergoes dehydrochlorination.
Health Hazard
LINDANE is a stimulant of the nervous system, causing violent convulsions that are rapid in onset and generally followed by death or recovery within 24 hours. The probable human oral lethal dose is 50-500 mg/kg, or between 1 teaspoon and 1 ounce for a 150-lb (70 kg) person.
Health Hazard
High acute toxicity; symptoms — headache,dizziness, nausea, vomiting, diarrhea, tremor,cyanosis, epileptic convulsions; stimulant tonervous system, which can lead to violent convulsions; such convulsions may setrapidly that may either progress to recovery within 24 hours or could lead to death(Hayes 1982); ingestion of 2–10 g probably fatal to human; an irritant to eyeand skin; chronic exposure causes liverinjury; oral LD50 value (mice): 86 mg/kg;carcinogenic to animals, causing liver andlung tumors; exposure limit: TLV : TWA(skin) 0.5 mg/m
3 (ACGIH, MSHA, andOSHA); RCRA Waste Number U120.
Fire Hazard
When heated to decomposition, LINDANE emits toxic fumes of chlorine, hydrochloric acid, and phosgene.
Agricultural Uses
Insecticide, Rodenticide: Lindane has been used against insects in a wide
range of applications including treatment of animals,
buildings, man for ectoparasites, clothes, water for mosquitoes,
living plants, seeds and soils. Most applications
have been canceled due to excessive residues, e.g., stored
foodstuffs, that may cause cancer. Formulators, distributors
and users of lindane represent a special risk group.
The major use of lindane in recent years has been to pretreat
seeds. Other uses include sunflowers, peas, wheat,
barley and oats. Lindane is currently also used in lotions,
creams and shampoos for the control of lice and mites
in humans. Not approved for use in EU countries. A
U.S. EPA restricted Use Pesticide (RUP). Lindane should
be handled as a carcinogen, with extreme caution. Most
applications have been canceled. It has not been produced
in the U.S. since 1977; however, it is still imported into
the U.S. and formulated to treat head lice, body lice and
scabies.
Trade name
AALINDAN®; AFICIDE®;
AGRISOL G-20®; AGROCIDE®; AGRONEXIT®;
AMEISENATOD®; AMEISENMITTEL (MERCK)®;
APARASIN®; APHTIRIA®; APLIDAL®; ARBITEX®;
BEN-HEX®; BENTOX 10®; CELANEX®;
CHLORESENE®; CODECHINE®; DELSANEX
DAIRY FLY SPRAY®; DETMOL-EXTRAKT®; DETOX
25®; DEVORAN®; DOL GRANULE®; DRILL TOXSPEZIAL
AGLUKON®; DUAL MURGANIC RPB SEED
TREATMENT®; ENTOMOXAN®; EXAGAMA®;
FORLIN®; GALLOGAMA®; GAMACID®;
GAMAPHEX®; GAMENE®; GAMMA-COL®;
GAMMALIN®; GAMMALIN 20; GAMMALEX®;
GAMMASAN 30®; GAMMATERR®; GAMMAPHEX®;
GAMMEX®; GAMMEXANE®; GAMMEXENE®;
GAMMOPAZ®; GEXANE®; HECLOTOX®; HEXA®;
HEXAFLOW®; HEXATOX®; HEXAVERM®;
HEXICIDE®; HEXYCLAN®; HORTEX®; INEXIT®;
ISOTOX®; JACUTIN®; KOKOTINE®; KWELL®;
LENTOX®; LINDAGRAM®; LIDENAL®; LINDAFOR®;
LINDAGAM®; LINDAGRAIN®; LINDAGRANOX®;
LINDAPOUDRE®; LINDATOX®; LINDOSEP®;
LINTOX®; LOREXANE®; MARSTAN FLY SPRAY®;
MERGAMMA 30®; MILBOL 49®; MIST-O-MATIC
LINDEX®; MSZYCOL®; NEXEN FB®; NEXIT®;
NEXIT-STARK®; NEXOL-E®; NICOCHLORAN®;
NOVIGAM®; OMNITOX®; OVADZIAK®;
OWADZIAK®; PEDRACZAK®; PFLANZOL®;
QUELLADA®; RODESCO INSECT POWDER®;
SANG GAMMA®; SILVANO®; SPRITZ-RAPIDIN®;
SPRUEHPFLANZOL®; STREUNEX®; TAP 85®; TRI-
6®; VITON®
Contact allergens
Lindane is a pesticide used for its antiinsect properties in agriculture, wood protection, in antiinsect paints and veterinary and human medicine against many and veterinary and human medicine against many and demodicidosis. Its use is controlled, particularlybecause of neurological toxicity
Clinical Use
Lindane is 1,2,3,4,5,6-hexachlorocyclohexane, -benzenehexachloride, or benzene hexachloride (Kwell, Scabene,Kwildane, G-Well). This halogenated hydrocarbon is preparedby the chlorination of benzene. A mixture of isomersis obtained in this process, five of which have been isolated:α, β, γ, δ, and ε. The γ-isomer, present to 10% to 13% inthe mixture, is responsible for the insecticidal activity. The -isomer may be separated by various extraction and chromatographictechniques.Lindane occurs as a light buff to tan powder with a persistentmusty odor, and it is bitter. It is insoluble in water butsoluble in most organic solvents. It is stable under acidic orneutral conditions but undergoes elimination reactions underalkaline conditions.The action of lindane against insects is threefold: it is a directcontact poison, it has a fumigant effect, and it acts as astomach poison. The effect of lindane on insects is similar tothat of DDT. Its toxicity in humans is somewhat lower thanthat of DDT. Because of its lipid solubility properties, however,lindane when ingested tends to accumulate in the body.Lindane is used locally as a cream, lotion, or shampoo forthe treatment of scabies and pediculosis.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic and
neoplastigenic data. A human systemic
poison by ingestion. Also a poison by
ingestion, skin contact, intraperitoneal,
intravenous, and intramuscular routes.
Human systemic effects by ingestion:
convulsions, dyspnea, and cyanosis.
Experimental teratogenic and reproductive
effects. Mutation data reported. See also
BENZENE HEXACHLORIDE and other
benzene hexachloride entries. When heated
to decomposition it emits toxic fumes of
Cl-, HCl, and phosgene.
Potential Exposure
The major commercial usage of BHC
is based upon its insecticidal properties. α-BCH is used as
an Agricultural chemical, pesticide, pharmaceutical, and
veterinary drug. The 7-isomer has the highest acute toxic ity, but the other isomers are not without activity. It is gen erally advantageous to purify the 7-isomer from the less
active isomers. The γ-isomer acts on the nervous system of
insects, principally at the level of the nerve ganglia. As a
result, lindane has been used against insects in a wide range
of applications including treatment of animals, buildings,
humans for ectoparasites, clothes; water for mosquitoes;
living plants; seeds and soils. Some applications have been
abandoned due to excessive residues, e.g., stored food stuffs. By voluntary action, the principal domestic producer
of technical grade BHC requested cancellation of its BHC
registrations on September 1, 1976. As of July 21, 1978, all
registrants of pesticide products containing BHC voluntar ily canceled their registrations or switched their former
BHC products to lindane formulations.
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 contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.
Carcinogenicity
Lindane (as γ-hexachlorocyclohexane), hexachlorocyclohexan
e (technical grade), and other hexachlorocyclohexane isomers are reasonably anticipated to be human carcinogens based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate
Biological. In a laboratory experiment, a strain of Pseudomonas putida culture transformed
lindane to g-3,4,5,6-tetrachlorocyclohexane (g-TCCH), g-pentachlorocyclohexane
(g-PCCH) and a-BHC (Benezet and Matsumura, 1973). g-TCCH was also reported as a
product of lindane degradation by Clostridium sphenoides (MacRae et al., 1969; Heritage
and MacRae, 1977, 1977a), an anaerobic bacterium isolated from flooded soils (MacRae
et al., 1969; Sethunathan and Yoshida, 1973a). Lindane degradation by Escherichia coli
also yielded g-PCCH (Francis et al., 1975). Evidence suggests that degradation of lindane
in anaerobic cultures or flooded soils amended with lindane occurs via reductive dehalogenation
producing chlorine-free volatile metabolites (Sethunathan and Yoshida, 1973a).
After a 30-day incubation period, the white rot fungus Phanerochaete chrysosporium
converted lindane to carbon dioxide. Mineralization began between the third and sixth day
of incubation. The production of carbon dioxide was highest between 3 to 18 days o
Beland et al. (1976) studied the degradation of lindane in sewage sludge under anaerobic
conditions. Lindane underwent reductive hydrodechlorination forming 3,4,5,6-tetrachlorocyclohex-
1-ene (g-BTC). The amount of g-BTC that formed reached a maximum
conc
When lindane was incubated in aerobic and anaerobic soil suspensions for 3 weeks,
0 and 63.8% was lost, respectively (MacRae et al., 1984). Using settled domestic wastewater
inoculum, lindane (5 and 10 mg/L) did not degrade after 28 days of incubation at
25°C (Tabak et al., 1981).
Soil. In moist soils, lindane biodegraded to g-pentachlorocyclohexene (Elsner et al.,
1972; Kearney and Kaufman, 1976; Fuhremann and Lichtenstein, 1980). Under anaerobic
conditions, degradation by soil bacteria yielded g-BTC and a-BHC (Kobayashi
Metabolic pathway
The metabolic pathways of gamma-HCH are complex and more than 80
metabolites have been identified (Macholz and Kujawa, 1985). Dehydrohalogenation
reactions are important. Gamma-HCH may be converted
into other HCH isomers in the environment and also microorganisms and
plants may convert gamma-HCH (1) into the alpha (2), beta (3), or delta
(4) isomers (see Schemel). Bioisomerisation does not appear to be a significant
pathway in mammals. In animals, metabolism of gamma-HCH
generally leads to less-chlorinated, unsaturated metabolites. Chlorinated
phenols may be formed and excreted as glucuronides. In a detailed discussion
of the biodegradation of gamma-HCH, the reaction mechanisms
involved were critically reviewed (Kurihara and Nakajima, 1980).
Oxygenation or glutathione conjugation are important initial stages in
metabolism. Key intermediates in the metabolic pathways are hexachlorocyclohexene
(18), pentachlorocyclohexene (5) and tetrachlorocyclohexene
(6) and these have been identified in a number of organisms
(Macholz and Kujawa, 1985).
Solubility in water
Wt % at 20 °C: 30.31 in acetone, 22.42 in benzene, 19.35 in chloroform, 17.22 in ether, 6.02 in
ethanol (Windholz et al., 1983)
9.76 and 13.97 g/L in hexane at 10 and 20 °C, respectively (shake flask-GC, Mills and Biggar,
1969)
92.8 g/kg in triolein at 25 °C (Chiou and Manes, 1986)
storage
Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly sealed containers in a cool, dryplace away from light and incompatible materials. Protectcontainers against physical damage. A regulated, markedarea should be established where this chemical is handled,used, or stored in compliance with OSHA Standard1910.1045.
Shipping
UN2761 Organochlorine pesticides, solid, toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Purification Methods
Crystallise it from EtOH. Purify it also by zone melting. Possible CANCER AGENT, TOXIC. [: Beilstein 1 H 23, : Beilstein 5 I 8, many isomers : Beilstein 5 III 41, 5 IV 55.]
Degradation
Gamma-HCH is extremely stable to light, air, temperatures up to 180 °C,
and to acids. It undergoes dechlorination in alkalis with DT
50 values
(22 °C) of 191 days (pH 7) and 11 hours (pH 9). It is photodegraded in
organic solvents (2-propanol or methanol) by UV irradiation (254 nm).
Toxicity evaluation
The acute toxicity of lindane depends on the age, sex, and
animal species, and on the route of administration. The
oral LD
50 in mice, rats, and guinea pigs is 86, 125–230,
and 100–127 mg/kg, respectively. In contrast, most of
the other isomers were considerably more toxic (94,95).
Some of the other toxic responses caused by lindane in
laboratory animals include hepato- and nephrotoxicity,
reproductive and embryotoxicity, mutagenicity in some
short-term in vitro bioassays, and carcinogenicity (80). The
mechanism of the lindane-induced response is not known.
Only minimal data are available on the mammalian
toxicities of hexachlorocyclopentadiene.
Incompatibilities
Lindane decomposes on contact with
powdered iron, aluminum, and zinc and with alkalis producing trichlorobenzene. Corrosive to metals
Waste Disposal
For the disposal of lindane, a
process has been developed involving destructive pyrolysis
@ 400-500℃ with a catalyst mixture which contains
5%-10% of either cupric chloride, ferric chloride; zinc
chloride; or aluminum chloride on activated carbon.
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.
