Methoprene

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Methoprene[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
1-methylethyl (E,E)-11- methoxy-3,7,11-trimethyl- 2,4-dodecadienoate
Other names
Methoprene, Altosid, Apex, Diacan, Dianex, Kabat, Minex, Pharorid, Precor, ZR-515
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.049.977 Edit this at Wikidata
KEGG
MeSH C093000
UNII
  • InChI=1S/C19H34O3/c1-15(2)22-18(20)14-17(4)11-8-10-16(3)12-9-13-19(5,6)21-7/h8,11,14-16H,9-10,12-13H2,1-7H3/b11-8+,17-14+ ☒N
    Key: NFGXHKASABOEEW-LDRANXPESA-N ☒N
  • InChI=1/C19H34O3/c1-15(2)22-18(20)14-17(4)11-8-10-16(3)12-9-13-19(5,6)21-7/h8,11,14-16H,9-10,12-13H2,1-7H3/b11-8+,17-14+
    Key: NFGXHKASABOEEW-LDRANXPEBN
  • CC(C)(OC)CCCC(C)C/C=C/C(C)=C/C(OC(C)C)=O
Properties
C19H34O3
Molar mass 310.48 g/mol
Appearance Liquid
Boiling point 100 °C (212 °F; 373 K) at 0.05 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Methoprene is a juvenile hormone (JH) analog which acts as a growth regulator when used as an insecticide. It is an amber-colored liquid with a faint fruity odor which is essentially nontoxic to humans when ingested or inhaled. It is used in drinking water cisterns to control mosquitoes which spread dengue fever and malaria.[2]

Methoprene does not kill insects. Instead, it acts as a Insect growth regulator, mimicking natural juvenile hormone. Juvenile hormone must be absent for a pupa to molt to an adult, so methoprene-treated larvae will be unable to successfully change from pupae to adults. This breaks the biological life cycle of the insect, preventing recurring infestation. Methoprene is used in the production of a number of foods, including meat, milk, mushrooms, peanuts, rice, and cereals. It also has several uses on domestic animals (pets) for controlling fleas. Methoprene is considered a biological pesticide because rather than controlling target pests through direct toxicity, methoprene interferes with an insect’s lifecycle and prevents it from reaching maturity or reproducing.[3]

Methoprene is commonly used as a mosquito larvicide used to help stop the spread of the West Nile virus.

Methoprene is also used as a food additive in cattle feed to prevent fly breeding in the manure.

Methoprene may be responsible for killing and stunting the growth of lobsters.[4]

References

  1. ^ Merck Index, 11th Edition, 5906.
  2. ^ "Methoprene" (PDF). Water Sanitation and Health. World Health Organization. 2008.
  3. ^ "Insect Growth Regulators: S-Hydroprene (128966), S-Kinoprene (107502), Methoprene (105401), S-Methoprene (105402) Fact Sheet" (PDF). U.S. Environmental Protection Agency Office of Pesticide Programs.
  4. ^ Walker, A. N.; Bush, P.; Puritz, J.; Wilson, T.; Chang, E. S.; Miller, T.; Holloway, K.; Horst, M. N. (2005). "Bioaccumulation and Metabolic Effects of the Endocrine Disruptor Methoprene in the Lobster, Homarus americanus" (PDF). Integrative and Comparative Biology. 45 (1): 118–26. doi:10.1093/icb/45.1.118.{{cite journal}}: CS1 maint: multiple names: authors list (link)

External links


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