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Methoxychlor

From Wikipedia, the free encyclopedia
Synthetic organochloride insecticide
Methoxychlor
Structural formula of methoxychlor
Ball-and-stick model of the methoxychlor molecule
Names
Preferred IUPAC name
1,1′-(2,2,2-Trichloroethane-1,1-diyl)bis(4-methoxybenzene)
Other names
Methoxcide
Dimethoxy-DDT
Methoxy-DDT
p,p'-Dimethoxydiphenyltrichloroethane
Identifiers
3D model (JSmol)
AbbreviationsDMDT
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.000.709Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C16H15Cl3O2/c1-20-13-7-3-11(4-8-13)15(16(17,18)19)12-5-9-14(21-2)10-6-12/h3-10,15H,1-2H3 checkY
    Key: IAKOZHOLGAGEJT-UHFFFAOYSA-N checkY
  • InChI=1/C16H15Cl3O2/c1-20-13-7-3-11(4-8-13)15(16(17,18)19)12-5-9-14(21-2)10-6-12/h3-10,15H,1-2H3
    Key: IAKOZHOLGAGEJT-UHFFFAOYAO
  • ClC(Cl)(Cl)C(c1ccc(OC)cc1)c2ccc(OC)cc2
Properties
C16H15Cl3O2
Molar mass345.65 g/mol
AppearanceColorless to light-yellow crystals
OdorSlight, fruity odor
Density1.41 g/cm3 (20°C)[1]
Melting point87 °C (189 °F; 360 K)
Boiling pointdecomposes
0.00001% (20°C)[1]
Hazards
Lethal dose or concentration (LD, LC):
5000 mg/kg (oral, rat)
1000 mg/kg (oral, mouse)
>6000 mg/kg (oral, rabbit)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 15 mg/m3[1]
REL (Recommended)
Ca[1]
IDLH (Immediate danger)
Ca [5000 mg/m3][1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Methoxychlor is a syntheticorganochlorideinsecticide, now obsolete. Tradenames for methoxychlor includeChemform,Maralate,Methoxo,Methoxcide,Metox, andMoxie.

Usage

[edit]

Methoxychlor was used to protect crops, ornamentals, livestock, and pets against fleas, mosquitoes, cockroaches, and other insects. It was intended to be a replacement forDDT, but has since been banned for use as a pesticide based on its acute toxicity,bioaccumulation, and endocrine disruption activity.[3]

The amount of methoxychlor in theenvironment 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 detected insediments.[4] Its degradation may take many months. Methoxychlor is ingested and absorbed by living organisms, and it accumulates in the food chain. Some metabolites may have unwanted side effects.

Banned

[edit]

The use of methoxychlor as apesticide was banned in theUnited States in 2003[5] and in theEuropean Union in 2002.[6]

Health and environmental impacts

[edit]

The EPA lists methoxychlor as "apersistent, bioaccumulative, and toxic (PBT) chemical by the EPA Toxics Release Inventory (TRI) program",[3] and as such it is a waste minimization priority chemical. The 2023 Conference of the Parties of theUnited NationsStockholm Convention on Persistent Organic Pollutants decided to eliminate the use of methoxychlor, by listing this chemical in Annex A to the Convention.[7]

Human exposure

[edit]

Human exposure to methoxychlor occurs via air, soil, and water,[8] 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.[8] Inanimal models, high doses can lead toneurotoxicity.[8] Some methoxychlor's metabolites haveestrogenic effects in adult and developing animals before and after birth.[8] One studied metabolite is2,2-bis(p-hydroxyphenyl)-1,1,1-trichloroethane (HPTE) which shows reproductive toxicity in an animal model by reducing testosterone biosynthesis.[9][10] Such effects adversely affect both the male and femalereproductive systems. It is expected that this "could occur in humans" but has not been proven.[8] While one study has linked methoxychlor to the development ofleukemia in humans, most studies in animals and humans have been negative, thus the EPA has determined that it is not classifiable as acarcinogen. The EPA indicates that levels above theMaximum Contaminant Level of 40 ppb "cause" central nervous depression, diarrhea, damage to liver, kidney, and heart, and - by chronic exposure - growth retardation.[3]

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[8] 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 anendocrine disruptor.[citation needed]

Food contamination may occur at low levels and it is recommended to wash all foods.[8] A number ofhazardous waste sites are known to contain methoxychlor.

Maximum pesticide residue limits for the EU/UK are set at 0.01 mg/kg for oranges and 0.01 mg/kg for apples.

See also

[edit]

References

[edit]
  1. ^abcdeNIOSH Pocket Guide to Chemical Hazards."#0388".National Institute for Occupational Safety and Health (NIOSH).
  2. ^"Methoxychlor".Immediately Dangerous to Life or Health Concentrations (IDLH).National Institute for Occupational Safety and Health (NIOSH).
  3. ^abcUnited States Environmental Protection Agency (2006-11-26)."Consumer Factsheet on: METHOXYCHLOR". Archived fromthe original on April 2, 2003.
  4. ^Karickhoff; et al. (1979). "Sorption of Hyrdophobic Pollutants on Natural Sediments".Water Research.13 (3):241–248.Bibcode:1979WatRe..13..241K.doi:10.1016/0043-1354(79)90201-x.
  5. ^U.S. Environmental Protection Agency (June 30, 2004)."Methoxychlor Reregistration Eligibility Decision (RED) EPA Publication No. EPA 738-R-04-010". Archived fromthe original on November 19, 2004. Retrieved2009-10-02.
  6. ^European Union - DG SANCO."EU Pesticides Database". Retrieved2009-10-02.
  7. ^"Governments accelerate action and take bold decisions to address pollution from chemicals and wastes". Secretariat of the Basel, Rotterdam and Stockholm Conventions. May 15, 2023. Retrieved7 July 2023.
  8. ^abcdefgATSDR (September 2002)."Public Health Statement about Methoxychlor"(PDF)., accessed 08-22-2008
  9. ^Akingbemi BT, et al. (2000)."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.62 (3):571–578.doi:10.1095/biolreprod62.3.571.PMID 10684797.
  10. ^Cummings AW (1997)."Methoxychlor as a model for environmental estrogens".Crit Rev Toxicol.27 (4):367–79.doi:10.3109/10408449709089899.PMID 9263644.

External links

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Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
Other chemicals
Metabolites
Biopesticides
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
CARTooltip Constitutive androstane receptor
PXRTooltip Pregnane X receptor
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