Methoprene

Basic Info

Common NameMethoprene(F06164)
2D Structure
FRCD IDF06164
CAS Number40596-69-8
PubChem CID5366546
FormulaC19H34O3
IUPAC Name

propan-2-yl (2E,4E)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate

InChI Key

NFGXHKASABOEEW-LDRANXPESA-N

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+

Canonical SMILES

CC(C)OC(=O)C=C(C)C=CCC(C)CCCC(C)(C)OC

Isomeric SMILES

CC(C)OC(=O)/C=C(\C)/C=C/CC(C)CCCC(C)(C)OC

Synonyms
        
            Pharoid
        
            Methoprene
        
            ALTOSID
        
            40596-69-8
        
            Diacon
        
            Dianex
        
            Juvemon
        
            Precor
        
            Kabat
        
            Manta
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassSesquiterpenoids
Intermediate Tree NodesNot available
Direct ParentSesquiterpenoids
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsSesquiterpenoid - Farsesane sesquiterpenoid - Fatty acid ester - Fatty acyl - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Carboxylic acid derivative - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Carbonyl group - Organic oxide - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Properties

Property NameProperty Value
Molecular Weight310.478
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count11
Complexity378
Monoisotopic Mass310.251
Exact Mass310.251
XLogP5.5
Formal Charge0
Heavy Atom Count22
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9175
Human Intestinal AbsorptionHIA+0.9853
Caco-2 PermeabilityCaco2+0.6945
P-glycoprotein SubstrateSubstrate0.5000
P-glycoprotein InhibitorNon-inhibitor0.6029
Inhibitor0.6913
Renal Organic Cation TransporterNon-inhibitor0.8621
Distribution
Subcellular localizationMitochondria0.7275
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8730
CYP450 2D6 SubstrateNon-substrate0.8979
CYP450 3A4 SubstrateSubstrate0.6263
CYP450 1A2 InhibitorNon-inhibitor0.8175
CYP450 2C9 InhibitorNon-inhibitor0.8091
CYP450 2D6 InhibitorNon-inhibitor0.9529
CYP450 2C19 InhibitorNon-inhibitor0.8276
CYP450 3A4 InhibitorNon-inhibitor0.9342
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8267
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9277
Non-inhibitor0.8881
AMES ToxicityNon AMES toxic0.9215
CarcinogensNon-carcinogens0.5341
Fish ToxicityHigh FHMT0.8703
Tetrahymena Pyriformis ToxicityHigh TPT0.9887
Honey Bee ToxicityHigh HBT0.8822
BiodegradationReady biodegradable0.7212
Acute Oral ToxicityIV0.6425
Carcinogenicity (Three-class)Non-required0.5630
Model Value Unit
Absorption
Aqueous solubility-5.1278LogS
Caco-2 Permeability1.1165LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.1248LD50, mol/kg
Fish Toxicity0.7612pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.4301pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Spinaches (Amaranths/Chinese spinaches/pak-khom, Amaranths/Chinese spinaches/pak-khom, Amaranths/Chinese spinaches/pak-khom, Amaranths/Chinese spinaches/pak-khom, Amaranths/Chinese spinaches/pak-kh...0252010European Union0.02*26/04/2013
Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe...0632010European Union0.1*26/04/2013
Beans (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, Ervils/lenti...0300010European Union0.05*26/04/2013
Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L...0256080European Union0.05*26/04/2013
Mulberries (black and white)0154060European Union0.02*26/04/2013
Citrus fruits0110000European Union0.02*26/04/2013
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.02*26/04/2013
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.02*26/04/2013
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.02*26/04/2013
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.02*26/04/2013
(a) edible peel0161000European Union0.02*26/04/2013
Dates (Açaí berries, Awara palm fruits, Doum palm fruits,)0161010European Union0.02*26/04/2013
Others (2)0110990European Union0.02*26/04/2013
Tree nuts0120000European Union0.05*26/04/2013
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.05*26/04/2013
Brazil nuts0120020European Union0.05*26/04/2013
Cashew nuts0120030European Union0.05*26/04/2013
Chestnuts0120040European Union0.05*26/04/2013
Coconuts (Areca nuts/betel nuts,)0120050European Union0.05*26/04/2013
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.05*26/04/2013

References

TitleJournalDatePubmed ID
Evaluation of Pyrethroid Insecticides and Insect Growth Regulators Applied toDifferent Surfaces for Control of Trogoderma granarium (Coleoptera: Dermestidae) the Khapra Beetle.J Econ Entomol2018 Apr 229514245
Transcriptional Analysis of The Adaptive Digestive System of The Migratory Locustin Response to Plant Defensive Protease Inhibitors.Sci Rep2016 Sep 127581362
A novel Cph-like gene involved in histogenesis and maintenance of midgut inBombyx mori.Pest Manag Sci2013 Dec23670814
Residual efficacy of methoprene for control of Tribolium castaneum (Coleoptera:Tenebrionidae) larvae at different temperatures on varnished wood, concrete, and wheat.J Econ Entomol2012 Apr22606845
Residual activity of methoprene and novaluron as surface treatments to manage theflour beetles, Tribolium castaneum and Tribolium confusum.J Insect Sci201223421852
[Analytical method for methoprene in foods using HPLC].Shokuhin Eiseigaku Zasshi2006 Aug16984038
The screening of chemicals for juvenoid-related endocrine activity using thewater flea Daphnia magna.Aquat Toxicol2005 Sep 1016046008
Development of a HPLC/tandem-MS method for the analysis of the larvicidesmethoprene, hydroprene, and kinoprene at trace levels using Diels-Alderderivatization.J Agric Food Chem2005 May 415853364
Rapid enzyme immunoassays for the detection of carbaryl and methoprene in grains.J Environ Sci Health B2002 Nov12403263
Synthesis of haptens and protein conjugates for the development of immunoassaysfor the insect growth regulator fenoxycarb.J Agric Food Chem2002 Jan 211754538
Biological activity of two juvenoids and two ecdysteroids against three storedproduct insects.Insect Biochem Mol Biol2000 Aug-Sep10876135
Effects of sustained-release methoprene and a combined formulation of liquid methoprene and Bacillus thuringiensis israelensis on insects in salt marshes.Arch Environ Contam Toxicol2000 Aug10871420