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Names | |||
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Systematic IUPAC name 1,2,4,5,6,7,8,8-Octachloro-3a,4,7,7a-tetrahydro-4,7-methanoindane | |||
Other names Chlordan; Chlordano; Ortho; Octachloro-4,7-methanohydroindane | |||
Identifiers | |||
ECHA InfoCard | 100.000.317 | ||
KEGG | |||
PubChem CID | |||
UNII | |||
CompTox Dashboard (EPA) | |||
Properties | |||
C10H6Cl8 | |||
Molar mass | 409.76 g·mol−1 | ||
Appearance | White solid | ||
Odor | Slightly pungent, chlorine-like | ||
Density | 1.59 g/cm3 | ||
Melting point | 102–106 °C (216–223 °F; 375–379 K) [1] | ||
Boiling point | decomposes [1] | ||
0.0001% (20°C) [1] | |||
Refractive index (nD) | 1.565 | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards | potential occupational carcinogen | ||
GHS labelling: | |||
Danger | |||
H301, H311, H351, H410 | |||
P201, P273, P280, P301+P310+P330, P302+P352+P312 [2] | |||
Flash point | 107 °C (225 °F; 380 K) (open cup) | ||
Explosive limits | 0.7–5% | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 590 mg/kg (rat, oral) 100 mg/kg (rabbit, oral) 430 mg/kg (mouse, oral) 300 mg/kg (rabbit, oral) 145 mg/kg (mouse, oral) 1720 mg/kg (hamster, oral) 200 mg/kg (rat, oral) [3] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 0.5 mg/m3 [skin] [1] | ||
REL (Recommended) | Ca TWA 0.5 mg/m3 [skin] [1] | ||
IDLH (Immediate danger) | 100 mg/m3 [1] | ||
Safety data sheet (SDS) | Chlordane (technical mixture) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Chlordane, or chlordan, is an organochlorine compound that was used as a pesticide. It is a white solid. In the United States, chlordane was used for termite-treatment of approximately 30 million homes until it was banned in 1988. [4] Chlordane was banned 10 years earlier for food crops like corn and citrus, and on lawns and domestic gardens. [5]
Like other chlorinated cyclodiene insecticides, chlordane is classified as an organic pollutant hazardous for human health. It is resistant to degradation in the environment and in humans/animals and readily accumulates in lipids (fats) of humans and animals. [6] Exposure to the compound has been linked to cancers, diabetes, and neurological disorders.
Technical chlordane development was by chance at Velsicol Chemical Corporation by Julius Hyman in 1948, during a search for possible uses of a by-product of synthetic rubber manufacturing. By chlorinating this by-product, persistent and potent insecticides were easily and cheaply produced. The chlorine atoms, 7 in the case of heptachlor, 8 in chlordane, and 9 in the case of nonachlor, surround and stabilize the cyclodiene ring and thus these compounds are referred to as cyclodienes. Other members of the cyclodiene family of organochlorine insecticides are aldrin and its epoxide, dieldrin, as well as endrin, which is a stereoisomer of dieldrin. Cyclodiene derives its name from hexachlorocyclopentadiene, a precursor in its production.
Hexachlorocyclopentadiene forms a Diels-Alder adduct with cyclopentadiene to give chlordene intermediate [3734-48-3]; chlorination of this adduct gives predominantly two chlordane isomers, α and β, in addition to other products such as trans-nonachlor and heptachlor. [7] The β-isomer is popularly known as gamma and is more bioactive. [5] The mixture that is composed of 147 components is called technical chlordane. [8] [9]
Chlordane appears as a white or off-white crystals when synthesized, but it was more commonly sold in various formulations as oil solutions, emulsions, sprays, dusts, and powders. These products were sold in the United States from 1948 to 1988.
Because of concern for harm to human health and to the environment, the United States Environmental Protection Agency (EPA) banned all uses of chlordane in 1983, except termite control in wooden structures (e.g. houses). After many reports of chlordane in the indoor air of treated homes, EPA banned the remaining use of chlordane in 1988. [10] The EPA recommends that children should not drink water with more than 60 parts of chlordane per billion parts of drinking water (60 ppb) for longer than 1 day. EPA has set a limit in drinking water of 2 ppb.[ citation needed ]
Chlordane is very persistent in the environment because it does not break down easily. Tests of the air in the residence of U.S. government housing, 32 years after chlordane treatment, showed levels of chlordane and heptachlor 10-15 times the Minimal Risk Levels (20 nanograms/cubic meter of air) published by the Centers for Disease Control.[ citation needed ] It has an environmental half-life of 10 to 20 years. [11]
In the years 1948–1988 chlordane was a common pesticide for corn and citrus crops, as well as a method of home termite control. [6] Pathways of exposure to chlordane include ingestion of crops grown in chlordane-contaminated soil, inhalation of air in chlordane-treated homes and from landfills, and ingestion of high-fat foods such as meat, fish, and dairy, as chlordane builds up in fatty tissue. [12] The United States Environmental Protection Agency reported that over 30 million homes were treated with technical chlordane or technical chlordane with heptachlor. Depending on the site of home treatment, the indoor air levels of chlordane can still exceed the Minimal Risks Levels (MRLs) for both cancer and chronic disease by orders of magnitude. [13] Chlordane is excreted slowly through feces, urine elimination, and through breast milk in nursing mothers. It is able to cross the placenta and become absorbed by developing fetuses in pregnant women. [14] A breakdown product of chlordane, the metabolite oxychlordane, accumulates in blood and adipose tissue with age. [15]
The examples and perspective in this article deal primarily with the United States and do not represent a worldwide view of the subject.(January 2017) |
Being hydrophobic, chlordane adheres to soil particles and enters groundwater only slowly, owing to its low solubility (0.009 ppm). It requires many years to degrade. [16] Chlordane bioaccumulates in animals. [17] It is highly toxic to fish, with an LD50 of 0.022–0.095 mg/kg (oral).
Oxychlordane (C10H4Cl8O), the primary metabolite of chlordane, and heptachlor epoxide, the primary metabolite of heptachlor, along with the two other main components of the chlordane mixture, cis-nonachlor and trans-nonachlor, are the main bioaccumulating constituents. [8] trans-Nonachlor is more toxic than technical chlordane and cis-nonachlor is less toxic. [8]
Chlordane and heptachlor are known as persistent organic pollutants (POP), classified among the "dirty dozen" and banned by the 2001 Stockholm Convention on Persistent Organic Pollutants. [18]
Exposure to chlordane/heptachlor and/or its metabolites (oxychlordane, heptachlor epoxide) are risk factors for type-2 diabetes, [19] for lymphoma, [20] for prostate cancer, [21] for obesity, [22] for testicular cancer, [23] for breast cancer. [24]
An epidemiological study conducted by the National Cancer Institute reported that higher levels of chlordane in dust on the floors of homes were associated with higher rates of non-Hodgkin lymphoma in occupants. [25] Breathing chlordane in indoor air is the main route of exposure for these levels in human tissues. Currently, EPA has defined a concentration of 24 nanogram per cubic meter of air (ng/M3) for chlordane compounds over a 20-year exposure period as the concentration that will increase the probability of cancer by 1 in 1,000,000 persons. This probability of developing cancer increases to 10 in 1,000,000 persons with an exposure of 100 ng/m3 and 100 in 1,000,000 with an exposure of 1000 ng/m3. [26]
The non-cancer health effects of chlordane compounds, which include diabetes, insulin resistance, migraines, respiratory infections, immune-system activation, anxiety, depression, blurry vision, confusion, intractable seizures as well as permanent neurological damage, [27] probably affects more people than cancer. Trans-nonachlor and oxychlordane in serum of mothers during gestation has been linked with behaviors associated with autism in offspring at age 4–5. [28] The Agency for Toxic Substances and Disease Registry (ATSDR) has defined a concentration of chlordane compounds of 20 ng/m3 as the Minimal Risk Level (MRLs). ATSDR defines Minimal Risk Level as an estimate of daily human exposure to a dose of a chemical that is likely to be without an appreciable risk of adverse non-cancerous effects over a specific duration of exposure. [29]
Chlordane was applied under the home/building during treatment for termites and the half-life can be up to 30 years. Chlordane has a low vapor pressure and volatilizes slowly into the air of home/building above. To remove chlordane from indoor air requires either ventilation (Heat Exchange Ventilation) or activated carbon filtration. Chemical remediation of chlordane in soils was attempted by the US Army Corps of Engineers by mixing chlordane with aqueous lime and persulfate. In a phytoremediation study, Kentucky bluegrass and Perennial ryegrass were found to be minimally affected by chlordane, and both were found to take it up into their roots and shoots. [30] Mycoremediation of chlordane in soil have found that contamination levels were reduced. [30] The fungus Phanerochaete chrysosporium has been found to reduce concentrations of chlordane by 21% in water in 30 days and in solids in 60 days. [31]
Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampricide. The most common of these are herbicides, which account for approximately 50% of all pesticide use globally. Most pesticides are intended to serve as plant protection products, which in general, protect plants from weeds, fungi, or insects. In general, a pesticide is a chemical or biological agent that deters, incapacitates, kills, or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, molluscs, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, or spread disease, or are disease vectors. Along with these benefits, pesticides also have drawbacks, such as potential toxicity to humans and other species.
Chlordecone, better known in the United States under the brand name Kepone, is an organochlorine compound and a colourless solid. It is an obsolete insecticide, now prohibited in the western world, but only after many thousands of tonnes had been produced and used. Chlordecone is a known persistent organic pollutant (POP) that was banned globally by the Stockholm Convention on Persistent Organic Pollutants in 2009.
Lindane, also known as gamma-hexachlorocyclohexane (γ-HCH), gammaxene, Gammallin and benzene hexachloride (BHC), is an organochlorine chemical and an isomer of hexachlorocyclohexane that has been used both as an agricultural insecticide and as a pharmaceutical treatment for lice and scabies.
Parathion, also called parathion-ethyl or diethyl parathion and locally known as "Folidol", is an organophosphate insecticide and acaricide. It was originally developed by IG Farben in the 1940s. It is highly toxic to non-target organisms, including humans, so its use has been banned or restricted in most countries. The basic structure is shared by parathion methyl.
Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion.
In organic chemistry, organophosphates are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents. They can be considered as esters of phosphoric acid.
Persistent organic pollutants (POPs) are organic compounds that are resistant to degradation through chemical, biological, and photolytic processes. They are toxic chemicals that adversely affect human health and the environment around the world. Because they can be transported by wind and water, most POPs generated in one country can and do affect people and wildlife far from where they are used and released.
Dieldrin is an organochlorine compound originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide. Dieldrin is closely related to aldrin, which reacts further to form dieldrin. Aldrin is not toxic to insects; it is oxidized in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels-Alder reaction which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene.
Toxaphene was an insecticide used primarily for cotton in the southern United States during the late 1960s and the 1970s. Toxaphene is a mixture of over 670 different chemicals and is produced by reacting chlorine gas with camphene. It can be most commonly found as a yellow to amber waxy solid.
Heptachlor is an organochlorine compound that was used as an insecticide. Usually sold as a white or tan powder, heptachlor is one of the cyclodiene insecticides. In 1962, Rachel Carson's Silent Spring questioned the safety of heptachlor and other chlorinated insecticides. Due to its highly stable structure, heptachlor can persist in the environment for decades. In the United States, the Environmental Protection Agency has limited the sale of heptachlor products to the specific application of fire ant control in underground transformers. The amount that can be present in different foods is regulated.
Aldrin is an organochlorine insecticide that was widely used until the 1990s, when it was banned in most countries. Aldrin is a member of the so-called "classic organochlorines" (COC) group of pesticides. COCs enjoyed a very sharp rise in popularity during and after World War II. Other noteworthy examples of COCs include dieldrin and DDT. After research showed that organochlorines can be highly toxic to the ecosystem through bioaccumulation, most were banned from use. Before the ban, it was heavily used as a pesticide to treat seed and soil. Aldrin and related "cyclodiene" pesticides became notorious as persistent organic pollutants.
Endosulfan is an off-patent organochlorine insecticide and acaricide that is being phased out globally. It became a highly controversial agrichemical due to its acute toxicity, potential for bioaccumulation, and role as an endocrine disruptor. Because of its threats to human health and the environment, a global ban on the manufacture and use of endosulfan was negotiated under the Stockholm Convention in April 2011. The ban took effect in mid-2012, with certain uses exempted for five additional years. More than 80 countries, including the European Union, Australia, New Zealand, several West African nations, the United States, Brazil, and Canada had already banned it or announced phase-outs by the time the Stockholm Convention ban was agreed upon. It is still used extensively in India and China despite laws against its use. It is also used in a few other countries. It is produced by the Israeli firm Makhteshim Agan and several manufacturers in India and China. On 13.05.2011, the India Supreme Court ordered a ban on the production and sale of endosulfan in India, pending further notice.
Endrin is an organochlorine compound with the chemical formula C12H8Cl6O that was first produced in 1950 by Shell and Velsicol Chemical Corporation. It was primarily used as an insecticide, as well as a rodenticide and piscicide. It is a colourless, odorless solid, although commercial samples are often off-white. Endrin was manufactured as an emulsifiable solution known commercially as Endrex. The compound became infamous as a persistent organic pollutant and for this reason it is banned in many countries.
Mirex is an organochloride that was commercialized as an insecticide and later banned because of its impact on the environment. This white crystalline odorless solid is a derivative of cyclopentadiene. It was popularized to control fire ants but by virtue of its chemical robustness and lipophilicity it was recognized as a bioaccumulative pollutant. The spread of the red imported fire ant was encouraged by the use of mirex, which also kills native ants that are highly competitive with the fire ants. The United States Environmental Protection Agency prohibited its use in 1976. It is prohibited by the Stockholm Convention on Persistent Organic Pollutants.
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Methoxychlor is a synthetic organochloride insecticide, now obsolete. Tradenames for methoxychlor include Chemform, Maralate, Methoxo, Methoxcide, Metox, and Moxie.
Phosmet is a phthalimide-derived, non-systemic, organophosphate insecticide used on plants and animals. It is mainly used on apple trees for control of codling moth, though it is also used on a wide range of fruit crops, ornamentals, and vines for the control of aphids, suckers, mites, and fruit flies.
Environmental toxicology is a multidisciplinary field of science concerned with the study of the harmful effects of various chemical, biological and physical agents on living organisms. Ecotoxicology is a subdiscipline of environmental toxicology concerned with studying the harmful effects of toxicants at the population and ecosystem levels.
Hexachlorocyclopentadiene (HCCPD), also known as C-56, Graphlox, and HRS 1655, is an organochlorine compound with the formula C5Cl6. It is a precursor to pesticides, flame retardants, and dyes. It is a colourless liquid, although commercial samples appear lemon-yellow liquid sometimes with a bluish vapour. Many of its derivatives proved to be highly controversial, as studies showed them to be persistent organic pollutants. An estimated 270,000 tons were produced until 1976, and smaller amounts continue to be produced today. Two prominent manufacturers are Velsicol Chemical Corporation in the US and by Jiangsu Anpon Electrochemicals Co. in China.
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