Mirex

Pesticide -> EPA IRIS

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organochlorine Pesticides

log Kow = 6.89

6.69

less than 1 mg/mL at 75 °F (NTP, 1992)

15.3% in dioxane at room temp; 14.3% in xylene at room temp; 12.2% in benzene at room temp; 7.2% in carbon tetrachloride at room temp; 5.6% in methyl ethyl ketone at room temp

In water, 0.085 mg/L at 25 °C

Decomposes above 500 °C to give hexachlorobenzene; hexachloropentadiene was found in small amounts in the thermal residue; the products identified from vapor phase were carbon monoxide, carbon dioxide, hydrogen chloride, chlorine, carbon tetrachloride, & phosgene.

905 °F (decomposes) (NTP, 1992)

485 °C (decomposes)

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P263, P264, P270, P273, P280, P301+P317, P302+P352, P317, P318, P321, P330, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

H301 (14.6%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P262, P263, P264, P270, P273, P280, P301+P316, P301+P317, P302+P352, P316, P317, P318, P321, P330, P361+P364, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Hazard Traits - Bioaccumulation; Carcinogenicity; Developmental Toxicity; Environmental Persistence; Hepatotoxicity and Digestive System Toxicity; Neurotoxicity; Reproductive Toxicity

Substance: Dodecachloropentacyclo[5.2.1.02,6.03,9.05,8]decane

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

INGESTION, INHALATION, OR SKIN EXPOSURE: Gas- trointestinal irritation with nausea, vomiting, and possible diarrhea. Malaise, headache, CNS excitation with tremor, paresthesias, ataxia, confusion, convulsions, and ventricular fibrillation. CNS depression and central respiratory paralysis may occur. (USCG, 1999)

Mirex and chlordecone are two separate, but chemically similar, manufactured insecticides that do not occur naturally in the environment. Mirex is a white crystalline solid, and chlordecone is a tan-white crystalline solid. Both chemicals are odorless. Mirex and chlordecone have not been manufactured or used in the United States since 1978. Mirex was used to control fire ants, and as a flame retardant in plastics, rubber, paint, paper, and electrical goods from 1959 to 1972. Chlordecone was used as an insecticide on tobacco, ornamental shrubs, bananas, and citrus trees, and in ant and roach traps. Mirex was sold as a flame retardant under the trade name Dechlorane, and chlordecone was also known as Kepone. Use of trade names is for identification only and does not imply endorsement by the Agency for Toxic Substances and Disease Registry, the Public Health Service, or the U.S. Department of Health and Human Services.

High-dose animal studies show that organochlorine insecticides can cause liver injury. [LaDou, p. 593] Causes moderate skin irritation, CNS stimulation, and liver injury; [HSDB]

Waters EM et al; Mirex I. An Overview. II. An Abstracted Literature Collection, 1947-1976, Toxicology Information Program, National Library of Medicine, ORNL/TIRC-76-4, Oak Ridge, TN, Oak Ridge National Laboratory, 93 pp (1976). An overview of the physical & chemical properties, metabolism, degradation, persistence, & bioaccumulation, & toxicology of mirex is presented.

DHHS/NTP; Toxicology & Carcinogenesis Studies of Mirex in F344/N Rats (Feed Studies) Technical Report Series No. 313 (1990) NIH Publication No. 90-2569

U.S. Dept Health & Human Services/Agency for Toxic Substances Disease Registry; Toxicological Profile for Mirex and Chlordecone (1995) NTIS# PB/95/264354

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Mirex (2385-85-5) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s115mire.pdf]

All registered products containing Mirex were effectively cancelled on December 1, 1977. (A technical Mirex product made by Hooker Chemical Company is unaffected by this Settlement Agreement. However since Mirex produced under this registration may be used only in the formulation of other pesticide products the registration was useless after December 1, 1977). All existing stocks of Mirex within the continental USA were not to be sold, distributed, or used after June 30, 1978.

Harvester Bait 300, Reg No 38962-5, may not be used for the control of the pheidole ant, Argentine ant, and fire ant on pineapples in Hawaii. The effective date of cancellation for these uses was December 1, 1977; existing stocks as of December 1, 1977 may not be applied aerially, but may be sold and used (other than aerially) indefinely.

The application of Harvester Bait 300 is subject to the following restrictions: 1. Aerial Application: No longer permitted. 2. Ground Application a. Permissible in all areas of infestation provided that there is no ground application to aquatic and heavily forested areas or areas where run-off or flooding will contaminate such areas. b. Treatment shall be confined to areas where the imported fire ants are causing significant problems. Note: the following definition is incl in order to clarify the ground application restrictions: Aquatic areas: encompasses without limitation estuaries, rivers, streams, wetlands (those land and water areas subject to inundation by tidal, riverine, or lacustrine flowage), lakes, ponds, and other bodies of water.

Mirex

Marine pollutant

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Liquid products containing organic solvents may be flammable. Extinguish fires with alcohol-resistant foam, carbon dioxide, or powder. With sufficient burning or external heat, mirex will decompose, emitting toxic fumes. Fire-fighters should wear a self-contained breathing apparatus, eye protection, and full protective clothing.

Products should be stored in locked buildings, preferably dedicated to insecticides. Keep products out of reach of children and unauthorized personnel. Do not store near foodstuffs or animal feed.

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practicable to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Before dealing with any spillage, precautions should be taken as required and appropriate personal protection should be used. Prevent liquid from spreading or contaminating other cargo and vegetation, and avoid pollution of surface waters and ground water by using the most suitable available material, e.g., earth or sand. Absorb spilled liquid with sawdust, sand, or earth, sweep up and place it in a closeable container for later transfer to a safe place for disposal. As soon as possible after the spillage and before re-use, cover all contaminated areas with damp sawdust, sand, or earth. Sweep up and place in a closeable container for later transfer to a safe place for disposal. Care should be taken to avoid run-off into surface waters or drains.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

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.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for MIREX (6 total), please visit the HSDB record page.

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/

For more Preventive Measures (Complete) data for MIREX (12 total), please visit the HSDB record page.

7.8 [mg/m3]

86 [mg/m3]

520 [mg/m3]

Mirex has been detected in adipose tissue from 6 human subjects at levels of 0.16-5.94 mg/kg. Avg residues of mirex in the fat of residents of states where mirex is applied were 1.32 mg/kg fat. Traces of mirex have been detected in some human milk samples at 0.1-0.6 ug/kg (wet-weight basis) and 2.3-21.5 ug/kg (fat basis).

Mirex tested positive in 0.1% of the human blood serum sampled from the general population with maximum concn of 1.70 ppb(1). Mirex tested positive in 0.29% of the human adipose tissues sampled from the general population in 1976 with a respective maximum and geometric average concn of 1.73 and 0.02 ppb(1). Mirex in human adipose tissue ranged in concn from 0.03 to 0.79 ppm for 8 of 8 samples in 1980 and from 0.12 to 0.17 ppm for 2 of 10 samples in 1984 at the St Francis Hospital, Monroe LA(2). The average concn of mirex found in human adipose tissue for 91 samples in Kingston and 84 samples in Ottawa, Canada were 27 and 11 ng/g, respectively(3). Only traces of mirex have been found in human breast milk in Canada(4). Mirex was detected in the human milk of 6, 16 and 6 maternity patients from Albany, Oswego and Rochester, NY at average concn of 0.070, 0.120 and 0.162 ng/g wet weight, respectively(5). The geometric mean concentration in breast milk for females residing in Mohawk Nation Akwesasne (upstate New York) was 1.8 ppb (1986-1989 sampling), 8.7 ppb (1990 sampling), and 12.5 ppb (1991-1992 sampling)(6). According to the National Health and Nutrition Examination Survey for years 2001-2002, the 90th and 95th percent confidence intervals for mirex levels in 2,257 samples of human serum for individuals 12 years of age and older in the US was 0.101 and 0.414 ng/g, respectively(7).

... The current study examines the effects of subchronic oral exposure to a complex mixture of ubiquitous persistent environmental contaminants that have been quantified in human reproductive tissues. The dosing solution used in this study contained organochlorines (2,3,7,8-tetrachlorodibenzo-p-dioxin [TCDD], polychlorinated biphenyls [PCBs],p,p'-dichlorodiphenoxydichloroethylene [p,p'-DDE],p,p-dichlorodiphenoxytrichloroethane [p,p'-DDT], dieldrin, endosulfan, methoxychlor, hexachlorobenzene, and other chlorinated benzenes, hexachlorocyclohexane, mirex and heptachlor) as well as metals (lead and cadmium). Each chemical was included in the mixture at the minimum risk level (MRL) or tolerable daily intake (TDI) as determined by the U.S. EPA or ATSDR or, for TCDD, at the no observable effect level (NOEL) used to calculate the TDI. Sexually mature male rats were exposed to this complex mixture at 1, 10, 100, and 1000 times the estimated safe levels daily for 70 days. On day 71, all animals were sacrificed and a variety of physiological systems assessed for toxic effects. Evidence of hepatotoxicity was seen in the significant enlargement of the liver in the 1000x group, reduced serum LDH activity (100x), and increased serum cholesterol and protein levels (both 1000x). Hepatic EROD activities were elevated in animals exposed to10x and above. The mixture caused decreased proliferation of splenic T cells at the highest dose and had a biphasic effect on natural killer cell lytic activity with an initial increase in activity at 1x followed by a decrease to below control levels in response to 1000x. No treatment-related effects were seen on bone marrow micronuclei, daily sperm production, serum LH, FSH, or prolactin levels or weights of most organs of the reproductive tract. The weights of the whole epididymis and of the caput epididymis were significantly decreased at 10x and higher doses, although no effect was seen on cauda epididymal weight. The sperm content of the cauda epididymis was increased at the 1x level but not significantly different from control at higher dose levels. A slight, but significant, increase in the relative numbers of spermatids was seen in the animals from the 1000x group with a trend towards reduced proportion of diploid cells at the same dose.

Reduced biliary excretion rates were observed for exogenous taurocholic acid (3 or 10 umol/kg) after 15 day dietary pretreatment of cannulated rats with 100 ppm mirex in feed. Hepatobiliary dysfunction was dose-dependent. Maximal redn in excretory rate on a per g of liver basis (50%) followed treatment with 100 ppm. Bile-to-plasma concn ratios for sucrose incr in parallel with mirex-impaired biliary excretion. Bile flow (on a per g of liver basis) & biliary clearance of erythritol were reduced by 100 ppm. These effects occurred in absence of substantial hepatocellular necrosis, whereas liver enlargement incr in a dose-dependent manner. Hepatobiliary dysfunction induced by mirex is at least partially due to increased permeability of the biliary tree.

The excretion of mirex was reduced when fed to captive American kestrels (Falco sparverius) at 8 ppm in combination with 33 ppm Aroclor 1254, & the combination diet reduced the relative concn of Aroclor in the testes. Testicular mass of the PCBs plus mirex group was increased. Apparently, migratory flesh-eating birds feeding on a PCB- or mirex-contaminated food chain could consume enough toxicant to alter their semen quality in that breeding season, which, when coupled with altered courtship, could reduce fertility of eggs & reproductive fitness.

Ring doves (Streptopelia risoria) with breeding experience were fed a control diet or 1 of 2 dosages of a mixture of DDE, PCBs, mirex, & photomirex throughout an isolated period of 90 days & 1 reproductive cycle. The mixture altered the nature & duration of courtship behavior, incubation & brooding behavior, & androgen levels of males, & estrogen & progesterone levels of females in a dose-related fashion. Thyroxine levels were incr in both sexes in dose-related fashion & there was an alteration of prolactin levels. Correlations were obtained between behavior & some hormones. There was marked dose-related decr of 15 & 50% in the number of squabs fledged/nesting attempt. Squabs of pairs receiving high dosage were of lower wt.

For more Interactions (Complete) data for MIREX (8 total), please visit the HSDB record page.

Cancer, Dermal (Skin), Endocrine (Glands and Hormones), Hepatic (Liver), Neurological (Nervous System), Ocular (Eyes), Renal (Urinary System or Kidneys), Reproductive (Producing Children)

Endocrine

LC50 Colinus virginianus (bobwhite quail) oral 2511 ppm in 5 day diet (95% confidence limit 2160-2908 ppm) /purity, 98%/

LC50 Japanese quail oral greater than 5000 ppm in 5 day diet (20% mortality at 5000 ppm) /purity, 98%/

LC50 Phasianus colchicus, (ring-necked pheasants) oral 1540 ppm in 5 day diet (95% confidence limit 1320-1789 ppm) /purity, 98%/

LC50 Anas platyrhynchos, (mallard ducks) oral greater than 5000 ppm in 5 day diet (no mortality to 5000 ppm) /purity 98%/

For more Ecotoxicity Values (Complete) data for MIREX (19 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 5800 measured in soil(2), indicates that mirex is expected to be immobile in soil(SRC). Volatilization of mirex from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 8.1X10-4 atm-cu m/mole(3); however, adsorption may attenuate this process(SRC). Mirex is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8X10-7 mm Hg(4). Mirex did not degrade (rate constant essentially zero) at a concn of 0.5 g/100g dry weight in nine soils maintained under aerobic conditions for six months(5).

AQUATIC FATE: Based on a classification scheme(1), an average Koc value of 2.4X10+7 obtained from 4 sediment samples(2), indicates that mirex is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 8.1X10-4 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 hours and 10 days, respectively(SRC). This estimation neglects the potentially important effect of adsorption on volatilization. The volatilization half-life from an environmental pond, which considers the effect of adsorption, can be estimated to be about 3.6 years if parameters are introduced into the pond model to include adsorption effects(5). According to a classification scheme(6), log BCF values of 2.3-5.5 measured in fish(7-10), suggest bioconcentration in aquatic organisms is high to very high(SRC). Mirex was resistant to biodegradation at a concn of 0.5 g/100 g dry weight in four anaerobic lake sediments after a 6 month incubation(11). Mirex at a concn of 33 ng/mL did not hydrolyze after 1 month at 100 °C in a purified water soln containing 1% acetonitrile and a pH of 7(2). A freshwater solution containing 1% acetonitrile with 33 ng/mL mirex, placed outdoors for 6 months, showed loss of mirex with a first order rate constant of 4.2X10-3 day-1 which corresponds to a half-life of about 330 days assuming 12 hours a day sunlight(2). Kepone and several isomers of monohydromirex were identified as the phototransformation products.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), mirex, which has a vapor pressure of 8X10-7 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Mirex does not contain functional groups that are susceptible to atmospheric degradation with photochemically generated hydroxyl radicals or ozone(3); however, direct photolysis in the atmosphere is expected to occur slowly(4,5). Particulate-phase mirex may be removed from the air by wet and dry deposition(SRC). The total atmospheric deposition flux rate (wet + dry) of mirex in Galveston Bay, TX was 0.04 ug/sq m-year(6).

A survey of items in human food chain showed that detectable residues of mirex were still present 1 yr after a single aerial application of mirex bait, at levels of 1.7 g/acre (4.2 g/ha). The levels observed in various species were: quail, 36 ug/kg; bluegill fish, 18 ug/kg; domestic chickens, 14 ug/kg; & chicken eggs, 1 ug/kg. /Louisiana l971-72/

Between 1972 and 1976 mirex tested positive in 4 samples or 0.1% of the 15,200 red meats evaluated with an average conc of 0.0003 ppm(1). Between 1972 and 1976 Mirex tested positive in 1 chicken or 0.02% of the 11,340 poultry samples evaluated with an average concn of 0.0001 ppm(1).

IN 2 OUT OF 3 SAMPLES OF COW'S MILK, /MIREX RESIDUES OF/ 0.007 & 0.016 PPM (FAT BASIS) HAVE BEEN FOUND. /Mississippi l970/

Only traces of mirex have been found in human breast milk in Canada(1). Mirex was detected in the human milk of 6, 16 and 6 maternity patients from Albany, Oswego and Rochester, NY at average concn of 0.070, 0.120 and 0.162 ng/g wet weight, respectively(2). The geometric mean concentration in breast milk for females residing in Mohawk Nation Akwesasne (upstate New York) was 1.8 ppb (1986-1989 sampling), 8.7 ppb (1990 sampling), and 12.5 ppb (1991-1992 sampling)(3).

All registered products containing Mirex were effectively cancelled on December 1, 1977. (A technical Mirex product made by Hooker Chemical Company is unaffected by this Settlement Agreement. However since Mirex produced under this registration may be used only in the formulation of other pesticide products the registration was useless after December 1, 1977). All existing stocks of Mirex within the continental USA were not to be sold, distributed, or used after June 30, 1978.

Harvester Bait 300, Reg No 38962-5, may not be used for the control of the pheidole ant, Argentine ant, and fire ant on pineapples in Hawaii. The effective date of cancellation for these uses was December 1, 1977; existing stocks as of December 1, 1977 may not be applied aerially, but may be sold and used (other than aerially) indefinely.

The application of Harvester Bait 300 is subject to the following restrictions: 1. Aerial Application: No longer permitted. 2. Ground Application a. Permissible in all areas of infestation provided that there is no ground application to aquatic and heavily forested areas or areas where run-off or flooding will contaminate such areas. b. Treatment shall be confined to areas where the imported fire ants are causing significant problems. Note: the following definition is incl in order to clarify the ground application restrictions: Aquatic areas: encompasses without limitation estuaries, rivers, streams, wetlands (those land and water areas subject to inundation by tidal, riverine, or lacustrine flowage), lakes, ponds, and other bodies of water.

Pretreatment of male rats with mirex (50 mg/kg orally for 3 days) caused a 91% suppression of biliary excretion of endogenous metabolites of imipramine. Biliary excretion of sulfobromophthalein was also suppressed by 90%. results suggest that mirex-induced impairment of hepatobiliary function is not specific to substrates. The mechanism of mirex-induced impairment is located at the site of the transfer of otherwise readily excretable substances such as metabolites of imipramine & sulfobromophthalein.

Mirex & its photoderivatives are effective inhibitors of ATPase system.

... Mirex .../is/ stored in lipid ... compartments of the body, which is the reason for ... /its/ very long elimination half-life ... /The/ very long half-live dominates the manifestation of damage ...

Mirex is a potent tumor promoter in 7,1 2-dimethylbenz[a]anthracene (DMBA)-initiated female CD-1 mouse skin. Like 12-O-tetradecanoylphorbol-13-acetate (TPA), mirex promotes papillomas that have a Ha-ras mutation; however, unlike TPA promotion, mirex promotion does not involve a general hyperplastic response. /The authors/ used proliferating cell nuclear antigen (PCNA) and 5-bromo-2'-deoxyuridine (BrdU) immunohistochemical staining to further examine the proliferative capacity of mirex. The numbers of PCNA- and BrdU-positive epidermal S-phase cells were highly concordant in all treatment groups. Unlike a single application of TPA, a single application of mirex had little or no effect on the number of S-phase epidermal cells, and chronic application of mirex to mouse skin produced only minimal increases in S-phase cells. Moreover, mirex did not significantly alter the growth of BALB/MK-2 keratinocytes in media containing either 0.05 or 1.2 mM Ca++. These results suggest that mirex may have highly specific effects on the proliferation of initiated cells and support the existence of a unique mirex mechanism and/or distinct population of mirex-promotable mutant Ha-ras epidermal cells. To begin to address this issue of a distinct population of mirex-promotable mutant Ha-ras cells, /the authors/ conducted a tandem experiment in which DMBA-initiated mice were treated twice weekly with a maximal promoting dose of mirex. Then, when the number of papillomas reached a plateau, these same mice were treated twice weekly with a maximal promoting dose of TPA. Mice treated with mirex developed a maximum of 6.4 papillomas/mouse. These mice were then promoted with TPA, which produced 8.9 additional papillomas/mouse for a total of 15.3 papillomas/mouse. The maximum tumor yields from other groups of mice treated with only TPA or mirex were 9.8 and 7.3 papillomas/mouse, respectively. Therefore, under these tandem conditions, tumor yields were additive, indicating that there are at least two distinct populations of mutant Ha-ras cells: one promoted by mirex and the other by TPA.

For more Mechanism of Action (Complete) data for MIREX (7 total), please visit the HSDB record page.

... IN RATS ... HALF LIVES FOR BIPHASIC EXCRETION OF MIREX WERE 38 HR & 100 DAYS, RESPECTIVELY.

In female goats, mirex levels decrease to one half their original concentration 34-52 wk after discontinuance of exposure. ...

Its elimination from the body is slow and, depending on the species, it has a half-life in the body of several months.

Preliminary disclosure that mirex yields no mammalian metabolites has ... been confirmed by a full report of long-term feeding trials in rat. In fat of female rats, concentrations of mirex had declined by only 40% some 10 mo after cessation of daily dosing. This ranks this polychlorinated cmpd ... as one of most persistent xenobiotics yet encountered.

Mirex is not metabolized by humans or animals ... .

Mirex ... is the fully chlorinated cage molecule ... that might be expected to be rather resistant to enzymatic attack ... One chlorine atom is reductively replaced in the environment to give photomirex (8-monohydro-mirex), which appears to behave like mirex in the rat. Reductive dechlorination can occur in vivo; 2,8-dihydromirex and 5,10-dihydromirex have been identified as rat metabolites. Whereas 2,8-dihydromirex does no appear to be further metabolized, 5,10-dihydromirex appears to be converted into more polar metabolites, which appear in rat urine.

Mirex is probably oxidized to chlordecone. The main metabolite of chlordecone is chlordecone alcohol, which appears in human bile as glucuronic acid conjugates.

Mirex is mainly absorbed through the gastrointestional tract, but may also be absorbed through the lungs and skin. Once absorbed, mirex is widely distributed throughout the body but is sequestered in the adipose tissue. It has a long retention time in the body. Mirex is not metabolized by humans and is excreted unchanged in the feces. (L601)

Mirex is transferred across the placenta to the fetus and is excreted with the milk.

Mirex is a lipophilic compound and as such is stored in the adipose tissue to a much greater extent than in any other tissue. For rats /that/ were dosed with a single oral dose of mirex at 6 mg/kg body weight, the tissues and organs retained about 34% of the total dose, of which 28% was found in fat, 3.2% in muscle, 0.09% in the kidneys, and 1.8% in the liver.

Following oral ingestion, mirex is only partly absorbed into the body and the remainder, depending on the dose administered, is eliminated unchanged in the faeces. Mirex can also be absorbed following inhalation and via the skin.

Approximately 55% of a single oral dose of 6 mg (14)C-mirex/kg body weight, administered to rats, was excreted unchanged in the feces within 48 hr. When a lower concentration of mirex was administered (0.2 mg/kg body weight), only 15% of the administered mirex was excreted in 48 hr.

For more Absorption, Distribution and Excretion (Complete) data for MIREX (17 total), please visit the HSDB record page.

Used formerly as fire retardant for plastics, rubber, paint, paper, and electrical products and as insecticide for fire ants; [Merck Index] All US production and uses ceased in the late 1970's; [HSDB]

All U.S. registrations cancelled; [EPA Pesticides, p. 56]

Pulp and Paper Processing [Category: Industry]

Mirex /is/ ... no longer made or used in the United States. Mirex /was/ ... most commonly used in the 1960s and 1970s. Mirex was used as a pesticide to control fire ants mostly in the southeastern part of the United States. It was also used extensively as a flame retardant additive under the trade name Dechlorane in plastics, rubber, paint, paper, and electrical goods from 1959 to 1972 because it does burn easily. ... All registered products containing mirex ... were canceled in the United States between 1977 and 1978.

Fire retardant for plastics, rubber, paint, paper, electrical goods. Formerly as insecticide for fire ants.

Mirex was most commonly used as an insecticide to control the imported fire ants (Solenopsis invicta and S. richteri) in Alabama, Arkansas, Florida, Georgia, Louisiana, Mississippi, North Carolina, South Carolina, and Texas.

(1972) SLIGHTLY MORE THAN 1.88X10+7 G

(1975) GREATER THAN 4.5X10+5 G

It had been formulated mainly as fine granules made from corn cobs impregnated with vegetable oil so that they serve as bait for fire ants. The concentration of oil is about 15% & that of the active ingredient /mirex/ may be 0.075, 0.15, or 0.3%.

Mirex has been formulated with aliphatic amines & ferrous chloride in an attempt to facilitate its photodegradation & to minimize its environmental contamination. The formulated product was known as ferriamicide.

Grade or purity: pelleted bait "450"-0.45% mirex

Food Contaminant -> CONTAMINANT; Food Contaminant -> -> JECFA Functional Classes

INSECTICIDES

US PATENT 2,671,043, MARCH 1954; US PATENT REISSUE 24,750, MARCH 1959. CODE NUMBER GC-1283 (ALLIED CHEMICAL).

Prepn: Prins, Rec Trav Chim 65, 455 (1946); Newcomer, McBee, J Am Chem Soc 71, 952 (1949); Gilbert, US patent 2,702,305 (1955 to Allied Chem); Johnson, US patent 2,724,730 (1955 to Hooker Electrochem)

Discontinued by Allied Chem Corp.