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Methoxychlor
Methoxychlor chemical structure.png
IUPAC name
Other names Methoxcide
Dimethoxy-DDT
Methoxy-DDT
Abbreviations DMDT
Identifiers
CAS number 72-43-5 Yes check.svgY
PubChem 4115
SMILES
Properties
Molecular formula C16H15Cl3O2
Molar mass 345.65 g mol−1
Melting point

87 °C, 360 K, 189 °F

Boiling point

decomposes

 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Methoxychlor is a synthetic organochlorine used as an insecticide.

Contents

Usage

The use of methoxychlor has been banned in the United States[1] and the European Union.[2] Methoxychlor is used to protect crops, ornamentals, livestock, and pets against fleas, mosquitoes, cockroaches, and other insects. It has been used to some degree as a replacement for DDT as it is metabolized faster and does not lead to bioaccumulation.

The amount of methoxychlor in the environment changes seasonally due to its use in farming and foresting. It does not dissolve readily in water, so it is mixed with a petroleum-based fluid and sprayed, or used as a dust. Sprayed methoxychlor settles on the ground or in aquatic ecosystems, where it can be found in sediments. Its degradation may take many months. Methoxychlor is ingested and absorbed by living organisms, but it is readily released, and does not accumulate in the food chain. Some metabolites may have unwanted side effects.

Human exposure

Human exposure to methoxychlor occurs via air, soil, and water[3], primarily in people who work with the substance or who are exposed to air, soil, or water that has been contaminated. It is unknown how quickly and efficiently the substance is absorbed by humans who have been exposed to contaminated air or via skin contact.[3] In high doses the agent can lead to neurotoxicity as observed in animal experiments.[3] Some of the agent's metabolites have estrogenic effect as shown in adult and developing animals before and after birth[3] One studied metabolite is 2,2-bis(p-hydroxyphenyl)- 1,1,1-trichloroethane (HPTE) which is considered to have reproductive toxicity in the animal model by reducing testosterone biosynthesis.[4][5] Such effects adversely affect the both the male and female reproductive systems. It is expected that this "could occur in humans" but has not been proven.[3] While one study has linked methoxychlor to the development of leukemia in humans, most studies in animals and humans have been negative, thus the EPA has determined that it is not classifiable as a carcinogen. The EPA indicates that levels above the Maximum Contaminant Level of 40 ppb "cause" central nervous depression, diarrhea, damage to liver, kidney, and heart, and - by chronic exposure - growth retardation.[6]

Little information is available regarding effects on human pregnancy and children, but it is assumed from animals studies that methoxychlor crosses the placenta, and it has been detected in human milk[3] Exposure to children may be different than in adults because they tend to play on the ground, further, their reproductive system may be more sensitive to the effects of methoxychlor as an endocrine disruptor.

Food contamination may occur at low levels and it is recommended to wash all foods.[3]. A number of hazardous waste sites are known to contain methoxychlor.

Labeling

Methoxychlor is not considered to be carcinogenic or teratogenic.

The EPA has labeled methoxychlor to be in the Toxicity Class IV which contains agents that are considered practically nontoxic and require no signal word. As such it is available as a General Use Pesticide (GUP). For drinking water, the United States Environmental Protection Agency (EPA) established 40ppb as the Maximum Contaminant Level (MCL).

Tradenames for methoxychlor include Chemform, Maralate, Methoxo, Methoxcide, Metox and Moxie.

References

  1. ^ U.S. Environmental Protection Agency (June 30, 2004). "Methoxychlor Reregistration Eligibility Decision (RED) EPA Publication No. EPA 738-R-04-010". http://www.epa.gov/oppsrrd1/REDs/methoxychlor_red.htm. Retrieved 2009-10-02.  
  2. ^ European Union - DG SANCO. "EU Pesticides Database". http://ec.europa.eu/sanco_pesticides/public/index.cfm?event=activesubstance.selection&a=1. Retrieved 2009-10-02.  
  3. ^ a b c d e f g ATSDR (September, 2002). "Public Health Statement about Methoxychlor". http://www.atsdr.cdc.gov/toxprofiles/tp47-c1-b.pdf.  , accessed 08-22-2008
  4. ^ Akingbemi BT et al.. "A Metabolite of Methoxychlor, 2,2-Bis(p-Hydroxyphenyl)-1,1,1-Trichloroethane, Reduces Testosterone Biosynthesis in Rat Leydig Cells Through Suppression of Steady-State Messenger Ribonucleic Acid Levels of the Cholesterol Side-Chain Cleavage Enzyme". Biology of Reproduction 2000;62;571-578.   http://www.biolreprod.org/cgi/content/full/62/3/571?maxtoshow=&HITS=&hits=&RESULTFORMAT=&fulltext=Benson+T.+Akingbemi+&searchid=1&volume=62&issue=3&resourcetype=HWCIT
  5. ^ Cummings AW. "Methoxychlor as a model for environmental estrogens.". Crit Rev Toxicol 1997;27:367-79.   PMID 9263644
  6. ^ United States Environmental Protection Agency (2006-11-26). "Consumer Factsheet on: METHOXYCHLOR". http://www.epa.gov/safewater/contaminants/dw_contamfs/methoxyc.html.  

See also

External links








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