リンダン

外観

白色, 結晶～粉末

溶解性

水に難溶。多くの有機溶媒に可溶。石油系の溶媒には微溶。水7.3(25℃), 12 (35℃) いずれもmg/l。アセトン43.5, メタノール7.4, エタノール6.4, ベンゼン28.9, トルエン27.6, キシレン24.7, ジエチルエーテル20.8, 石油エーテル2.9, 酢酸エチル35.7, クロロホルム24.0, 四塩化炭素6.7, シクロヘキサン36.7, ジオキサン, 31.4, 酢酸12アセトンにやや溶けやすく、エタノールに溶けにくく、水にほとんど溶けない。

用途

殺虫剤(販売禁止農薬) (NITE CHRIP)

効能

殺シラミ薬, 殺疥癬虫薬

農薬用途

殺虫剤

説明

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).

化学的特性

Lindane is a white to yellow, crystalline powder with a slight, musty odor (pure material is odorless).

物理的性質

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.

使用

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).

適応症

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.

世界保健機関（WHO）

Lindane has been available for more than 25 years and is widely used as an agricultural and household pesticide.

一般的な説明

Colorless solid with a musty odor; pure material is odorless. Used as a pesticide and scabicide.

空気と水の反応

Insoluble in water.

反応プロフィール

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.

健康ハザード

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.

火災危険

When heated to decomposition, LINDANE emits toxic fumes of chlorine, hydrochloric acid, and phosgene.

农业用途

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.

接触アレルゲン

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

臨床応用

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.

安全性プロファイル

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.

職業ばく露

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.

発がん性

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.

代謝経路

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).

輸送方法

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

純化方法

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.]

不和合性

Lindane decomposes on contact with powdered iron, aluminum, and zinc and with alkalis producing trichlorobenzene. Corrosive to metals

廃棄物の処理

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.