Methoprene: Difference between revisions

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{{redirect|Precor|the sports brand|Peloton Interactive}}
{{chembox
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| UNII = 8B830OJ2UX
| verifiedrevid = 445542563
| verifiedrevid = 445542563
| Reference = <ref>''Merck Index'', 11th Edition, '''5906'''.</ref>
| Reference = <ref>''Merck Index'', 11th Edition, '''5906'''.</ref>
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| ImageSize1 = 240px
| ImageSize1 = 240px
| ImageName1 = Ball-and-stick model
| ImageName1 = Ball-and-stick model
| IUPACName = 1-methylethyl (''E'',''E'')-11- methoxy-3,7,11-trimethyl- 2,4-dodecadienoate
| PIN = Propan-2-yl (2''E'',4''E'')-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
| OtherNames = Methoprene, Altosid, Apex, Diacan, Dianex, Kabat, Minex, Pharorid, Precor, ZR-515
| OtherNames = Methoprene, Altosid, Apex, Diacan, Dianex, Kabat, Minex, Pharorid, Precor, ZR-515
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| UNII = 8B830OJ2UX
⚫
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 40596-69-8
| CASNo = 40596-69-8
| PubChem = 5366546
| PubChem = 5366546
| SMILES = CC(C)(OC)CCCC(C)C/C=C/C (C)=C/C(OC(C)C)=O <!--CC(C)(OC)CCCC(C)C/C=C/C(C)=C/C(OC(C)C)=O-->
| SMILES = CC(C)(OC)CCCC(C)C/C=C/C(C)=C/C(OC(C)C)=O
⚫
| ATCvet = yes
⚫
| ATCCode_prefix = P53
⚫
| ATCCode_suffix = AX28
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14308
| KEGG = C14308
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4518347
| ChemSpiderID = 4518347
| 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+
| 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+
| InChIKey = NFGXHKASABOEEW-LDRANXPEBN
| InChIKey = NFGXHKASABOEEW-LDRANXPEBN
⚫
| StdInChI = 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+
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫
| StdInChIKey = NFGXHKASABOEEW-LDRANXPESA-N
⚫
| StdInChI = 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+
| RTECS =
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫
| MeSHName = C093000
⚫
| StdInChIKey = NFGXHKASABOEEW-LDRANXPESA-N
⚫
| ChEBI = 34839
| ChEMBL = 291057
| RTECS =
⚫
| MeSHName = C093000
| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫
| ChEBI = 34839
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 291057
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>19</sub>H<sub>34</sub>O<sub>3</sub>
| Formula = C<sub>19</sub>H<sub>34</sub>O<sub>3</sub>
| MolarMass = 310.48 g/mol
| MolarMass = 310.48 g/mol
| Appearance = Liquid
| Appearance = Liquid
| Density =
| Density =
| MeltingPt =
| MeltingPt =
| BoilingPt = 100 °C at 0.05 mmHg
| BoilingPtC = 100
| BoilingPt_notes = at 0.05 mmHg
| Solubility =
| Solubility =
⚫
}}
⚫
| Section3 = {{Chembox Hazards
⚫
| MainHazards =
⚫
| FlashPt =
| Autoignition =
}}
}}
⚫
|Section7={{Chembox Hazards
⚫
| MainHazards = Eye irritant
⚫
| FlashPt =
| AutoignitionPt =
⚫
}}
|Section6={{Chembox Pharmacology
⚫
| ATCvet = yes
⚫
| ATCCode_prefix = P53
⚫
| ATCCode_suffix = AX28
}}
}}
}}


'''Methoprene''' is a [[juvenile hormone]] (JH) [[analog (chemistry)|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.<ref>{{cite web | work = Water Sanitation and Health | publisher = [[World Health Organization]] | title = Methoprene | url= http://www.who.int/water_sanitation_health/dwq/chemicals/methoprenesum_2ndadd.pdf | accessdate = 2008}}</ref>
'''Methoprene''' is a [[juvenile hormone]] (JH) [[analog (chemistry)|analog]] which acts as a growth regulator when used as an [[insecticide]]. It is an amber-colored liquid with a faint fruity odor.


Methoprene does not kill insects. Instead, it interferes with an insect’s life cycle and prevents it from reaching maturity or
Methoprene does not kill adult insects. Instead, it acts as a [[Insect growth regulator|growth regulator]], mimicking natural [[juvenile hormone]] of insects. 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 biochemical 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.<ref>{{cite web | title = Insect Growth Regulators: S-Hydroprene (128966), S-Kinoprene (107502), Methoprene (105401), S-Methoprene (105402) Fact Sheet | publisher = [[U.S. Environmental Protection Agency]] | url = http://www.epa.gov/oppbppd1/biopesticides/ingredients/factsheets/factsheet_igr.htm | accessdate = 2007-09-09}}</ref> Methoprene is used most widely as the [[mosquito]] [[larvicide]] Altosid, which is an important measure in reduction of the spread of [[West Nile virus]].
reproducing.<ref>{{cite web |title=Update of the March 1991 Methoprene R.E.D. Fact Sheet |url=https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/fs_PC-105401_1-Jun-01.pdf |website=epa.gov |publisher=United States Environmental Protection Agency |access-date=2022-12-01 |archive-url=https://web.archive.org/web/20221020201454/https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/fs_PC-105401_1-Jun-01.pdf |archive-date=2022-10-20|language=en-US |date=June 2001 |url-status=live}}</ref> 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.<ref>{{ cite web | title = Insect Growth Regulators: S-Hydroprene (128966), S-Kinoprene (107502), Methoprene (10401), S-Methoprene (105402) Fact Sheet | publisher = [[U.S. Environmental Protection Agency]] Office of Pesticide Programs | url = http://www.epa.gov/opp00001/chem_search/reg_actions/registration/fs_G-107_06-Dec-01.pdf | date = 2015-08-20 }}</ref>
⚫
Methoprene is also used as a food additive in cattle feed to prevent fly breeding in the manure.


==Applications==
Methoprene may be responsible for killing and stunting the growth of [[lobster]]s in [[Narragansett Bay]].<ref>{{cite web | title = Are our lobsters casualties in war on mosquitoes? | url = http://www.projo.com/news/content/pesticide_vs_lobsters_06-17-08_1FADP78_v34.3e92bf0.html | accessdate = 2008-07-18}}</ref> However, considering the durability of the chemical in the environment (about two days), the lasting effect of the biological activity of the substance in the environment (about one week), it should be further investigated. <ref>{{cite journal | author = Madder, D. J.; Lockhart, W. L. | title = Studies on the Dissipation of Diflubenzuron and Methoprene from Shallow Prairie Pools | journal = The Canadian Entomologist | year = 1980 | volume = 112 | issue = 2 | pages = 173–7 | doi = 10.4039/Ent112173-2 }}</ref> These timelines, coupled with runoff of fresh surface waters into the ocean from inland areas, suggest it is very possible or likely that methoprene enters the ocean ecosystem in an active form. Studies would have to be conducted to test the hypothesis that methoprene interferes with the lifecycle of lobsters before a conclusion can be reached.
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]].<ref>{{cite web | work = Water Sanitation and Health | publisher = [[World Health Organization]] | title = Methoprene | url=https://www.who.int/water_sanitation_health/dwq/chemicals/methoprenesum_2ndadd.pdf | year = 2008 }}</ref> 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.

==Health and safety==

According to the Safety Data Sheet (SDS), 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.<ref>{{cite web | work = MSDS for Methoprene | publisher = Cayman Chemical | title = Methoprene Materials Safety Data Sheet | url = https://www.caymanchem.com/msdss/16807m.pdf | year = 2019}}</ref> 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 [[lobster]]s. Like insects and mites, lobsters are arthropods.<ref>{{ cite journal |author1=Walker, A. N. |author2=Bush, P. |author3=Puritz, J. |author4=Wilson, T. |author5=Chang, E. S. |author6=Miller, T. |author7=Holloway, K. |author8=Horst, M. N. | title = Bioaccumulation and Metabolic Effects of the Endocrine Disruptor Methoprene in the Lobster, ''Homarus americanus'' | journal = Integrative and Comparative Biology | year = 2005 | volume = 45 | issue = 1 | pages = 118–26 | doi = 10.1093/icb/45.1.118 | url = http://icb.oxfordjournals.org/content/45/1/118.full.pdf | pmid=21676752| doi-access=free }}</ref>


==References==
==References==
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* [http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_105401.pdf Methoprene Pesticide Fact Sheet - Environmental Protection Agency]
* [http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_105401.pdf Methoprene Pesticide Fact Sheet - Environmental Protection Agency]
* [http://extoxnet.orst.edu/pips/methopre.htm Methoprene Pesticide Information Profile - Extension Toxicology Network]
* [http://extoxnet.orst.edu/pips/methopre.htm Methoprene Pesticide Information Profile - Extension Toxicology Network]
* {{PPDB|459}}
* [http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/459.htm Pesticide Properties Database record for methoprene]



{{Insecticides}}
{{Insecticides}}
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[[Category:Ethers]]
[[Category:Ethers]]
[[Category:Dienes]]
[[Category:Dienes]]
[[Category:Isopropyl esters]]

Latest revision as of 20:37, 3 November 2023

"Precor" redirects here. For the sports brand, see Peloton Interactive.
Methoprene[1]
Skeletal formula
Ball-and-stick model
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
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
Pharmacology
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).
☒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.

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]

Applications[edit]

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.

Health and safety[edit]

According to the Safety Data Sheet (SDS), 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]

References[edit]

  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). MSDS for Methoprene. 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): 118–26. doi:10.1093/icb/45.1.118. PMID 21676752.

External links[edit]

Retrieved from "https://en.wikipedia.org/w/index.php?title=Methoprene&oldid=1183359800"