Methoprene

Methoprene^[1]
Names
	Preferred IUPAC name Propan-2-yl (2E,4E)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
	Other names Methoprene, Altosid, Apex, Diacan, Dianex, Kabat, Minex, Pharorid, Precor, ZR-515
Identifiers
CAS Number	40596-69-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34839 ;
ChEMBL	ChEMBL291057 ;
ChemSpider	4518347 ;
ECHA InfoCard	100.049.977
KEGG	C14308 ;
MeSH	C093000
PubChem CID	5366546;
UNII	8B830OJ2UX ;
CompTox Dashboard (EPA)	DTXSID8032627 ;
	InChI 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+ Key: NFGXHKASABOEEW-LDRANXPESA-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;
	SMILES CC(C)(OC)CCCC(C)C/C=C/C(C)=C/C(OC(C)C)=O;
Properties
Chemical formula	C19H34O3
Molar mass	310.48 g/mol
Appearance	Liquid
Boiling point	100 °C (212 °F; 373 K) at 0.05 mmHg
Pharmacology
ATCvet code	QP53AX28 (WHO)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Eye irritant
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

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Methoprene does not kill insects. Instead, it interferes with an insect’s life cycle and prevents it from reaching maturity or reproducing.^[2] Juvenile growth hormones 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 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 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.

It is used in drinking water cisterns to control mosquitoes which spread dengue fever and malaria.^[4] 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.

According to its materials safety data sheet (MSDS), methoprene is a material that may be irritating to the mucous membranes and upper respiratory tract; may be harmful by inhalation, ingestion, or skin absorption; may cause eye, skin, or respiratory system irritation; and is very toxic to aquatic life.^[5] The GHS signal word is "Warning", with notes such as "P273: Avoid release into the environment" and "P391: Collect spillage".

Methoprene is suspected to be highly toxic to lobsters. Like insects and mites, lobsters are arthropods.^[6]

[1]
Merck Index, 11th Edition, 5906.
[2]
"Update of the March 1991 Methoprene R.E.D. Fact Sheet" (PDF). epa.gov. United States Environmental Protection Agency. June 2001. Archived (PDF) from the original on 2022-10-20. Retrieved 2022-12-01.
[3]
"Insect Growth Regulators: S-Hydroprene (128966), S-Kinoprene (107502), Methoprene (10401), S-Methoprene (105402) Fact Sheet" (PDF). U.S. Environmental Protection Agency Office of Pesticide Programs. 2015-08-20.
[4]
"Methoprene" (PDF). Water Sanitation and Health. World Health Organization. 2008.
[5]
"Methoprene Materials Safety Data Sheet" (PDF). CaymanChem.org. Cayman Chemical. 2019.
[6]
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): 118–126. doi:10.1093/icb/45.1.118. PMID 21676752.

Methoprene Pesticide Fact Sheet - Environmental Protection Agency
Methoprene Pesticide Information Profile - Extension Toxicology Network
Methoprene in the Pesticide Properties DataBase (PPDB)

[1] [1]
Merck Index, 11th Edition, 5906.

[2] [2]
"Update of the March 1991 Methoprene R.E.D. Fact Sheet" (PDF). epa.gov. United States Environmental Protection Agency. June 2001. Archived (PDF) from the original on 2022-10-20. Retrieved 2022-12-01.

[3] [3]
"Insect Growth Regulators: S-Hydroprene (128966), S-Kinoprene (107502), Methoprene (10401), S-Methoprene (105402) Fact Sheet" (PDF). U.S. Environmental Protection Agency Office of Pesticide Programs. 2015-08-20.

[4] [4]
"Methoprene" (PDF). Water Sanitation and Health. World Health Organization. 2008.

[5] [5]
"Methoprene Materials Safety Data Sheet" (PDF). CaymanChem.org. Cayman Chemical. 2019.

[6] [6]
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): 118–126. doi:10.1093/icb/45.1.118. PMID 21676752.

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Methoprene

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