Basic Info

Common NameOxamyl(F04017)
2D Structure
Description

Oxamyl is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (L795)

FRCD IDF04017
CAS Number23135-22-0
PubChem CID9595287
FormulaC7H13N3O3S
IUPAC Name

methyl (1Z)-2-(dimethylamino)-N-(methylcarbamoyloxy)-2-oxoethanimidothioate

InChI Key

KZAUOCCYDRDERY-UITAMQMPSA-N

InChI

InChI=1S/C7H13N3O3S/c1-8-7(12)13-9-5(14-4)6(11)10(2)3/h1-4H3,(H,8,12)/b9-5-

Canonical SMILES

CNC(=O)ON=C(C(=O)N(C)C)SC

Isomeric SMILES

CNC(=O)O/N=C(/C(=O)N(C)C)\SC

Synonyms
        
            2-Dimethylamino-1-(methylthio)glyoxal O-methylcarbamoylmonoxime
        
            OXAMYL
        
            23135-22-0
        
            Dioxamyl
        
            Thioxamyl
        
            2-(Dimethylamino)-N-(((methylamino)carbonyl)oxy)-2-oxoethanimidothioic acid methyl ester
        
            S-Methyl 1-(dimethylcarbamoyl)-N-((methylcarbamoyl)oxy)thioformimidate
        
            Oxamyl, analytical standard
        
            methyl 2-(dimethylamino)-N-(methylcarbamoyloxy)-2-oxoethanimidothioate
        
            N',N'-dimethyl-N-((methylcarbamoyl)oxy)-1-methylthio-oxamimidic acid
        
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassCarboxylic acid derivatives
Intermediate Tree NodesCarboxylic acid amides
Direct ParentTertiary carboxylic acid amides
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsTertiary carboxylic acid amide - Carboximidic acid derivative - Sulfenyl compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Imine - Organic nitrogen compound - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as tertiary carboxylic acid amides. These are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H).

Properties

Property NameProperty Value
Molecular Weight219.259
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Complexity253
Monoisotopic Mass219.068
Exact Mass219.068
XLogP-0.5
Formal Charge0
Heavy Atom Count14
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8602
Human Intestinal AbsorptionHIA+0.9781
Caco-2 PermeabilityCaco2-0.5386
P-glycoprotein SubstrateNon-substrate0.8077
P-glycoprotein InhibitorNon-inhibitor0.7604
Non-inhibitor0.9019
Renal Organic Cation TransporterNon-inhibitor0.9574
Distribution
Subcellular localizationMitochondria0.6094
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7995
CYP450 2D6 SubstrateNon-substrate0.8506
CYP450 3A4 SubstrateNon-substrate0.6053
CYP450 1A2 InhibitorNon-inhibitor0.6689
CYP450 2C9 InhibitorNon-inhibitor0.7719
CYP450 2D6 InhibitorNon-inhibitor0.8991
CYP450 2C19 InhibitorNon-inhibitor0.6946
CYP450 3A4 InhibitorNon-inhibitor0.9556
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9588
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9921
Non-inhibitor0.9361
AMES ToxicityAMES toxic0.6264
CarcinogensCarcinogens 0.6196
Fish ToxicityHigh FHMT0.9584
Tetrahymena Pyriformis ToxicityLow TPT0.6445
Honey Bee ToxicityHigh HBT0.7987
BiodegradationNot ready biodegradable0.9422
Acute Oral ToxicityI0.8436
Carcinogenicity (Three-class)Non-required0.6989

Model Value Unit
Absorption
Aqueous solubility0.0472LogS
Caco-2 Permeability1.0480LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity4.0988LD50, mol/kg
Fish Toxicity0.7065pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.1131pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Cashew nuts0120030European Union0.01*14/08/2014
Coconuts (Areca nuts/betel nuts,)0120050European Union0.01*14/08/2014
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.01*14/08/2014
Carambolas (Ambarellas, Aonlas/Indian gooseberries, Babacos, Bilimbis, Cashew apples, Indian jujubes/bers, Jaboticabas, Malay pommarosas/pomeracs, Malayan mombins, Maprangs/marian plums, Natal plum...0161050European Union0.01*14/08/2014
Spring onions/green onions and Welsh onions (Tree onions/Egyptian walking onions, Green garlic,)0220040European Union0.01*14/08/2014
Tomatoes (Alkekengi/Chinese lanterns/ground cherries, Cape gooseberries, Cherry tomatoes, Dwarf Cape gooseberries/strawberry tomatoes, Gojiberries/wolfberries, Gojiberries/wolfberries, Litchi tomat...0231010European Union0.01*14/08/2014
(c) grape leaves and similar species (Climbing wattle/acacia shoots, Malabar nightshades,)0253000European Union0.01*14/08/2014
Celery leaves (Angelica (leaves and stems), Burnet, Caraway leaves, Coriander leaves, Culantro/false coriander leaves, Dill leaves, Fennel leaves, Fenugreek leaves, Herb of grace/rue, Lovage leaves...0256030European Union0.02*14/08/2014
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 Union0.02*14/08/2014
Algae and prokaryotes organisms (Carrageen mosses/Irish mosses, Kombu, Spirulina, Spirulina, Other algae, Other procaryotes organisms, Rockweed /knotted kelp,)0290000European Union0.01*14/08/2014
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 Union0.01*14/08/2014
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 Union0.05*14/08/2014
(g) other farmed terrestrial animals (Alpaca, Bactrian camel, Capybara, Cottontail/American rabbit, Dromedary, Eland, Elk/moose, Emu, Fallow deer, Guinea pig, Hare (farmed), Llama, Nandu/greater rh...1017000European Union0.01*14/08/2014
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.01*14/08/2014
Citrus fruits0110000European Union0.01*14/08/2014
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*14/08/2014
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*14/08/2014
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*14/08/2014
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*14/08/2014
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.01*14/08/2014

References

TitleJournalDatePubmed ID
Chemiluminescent Determination of Oxamyl in Drinking Water and Tomato UsingOnline Postcolumn UV Irradiation in a Chromatographic System.J Agric Food Chem2018 Mar 729442513
Dissipation rate study and pre-harvest intervals calculation of imidacloprid and oxamyl in exported Egyptian green beans and chili peppers after pestigationtreatment.Food Chem2018 Feb 128946222
Chronic cumulative risk assessment of the exposure to organophosphorus, carbamateand pyrethroid and pyrethrin pesticides through fruit and vegetables consumption in the region of Valencia (Spain).Food Chem Toxicol2016 Mar26774911
Fenugreek hydrogel-agarose composite entrapped gold nanoparticles foracetylcholinesterase based biosensor for carbamates detection.Anal Chim Acta2015 Jul 3026320646
Accelerated biodegradation of selected nematicides in tropical crop soils fromCosta Rica.Environ Sci Pollut Res Int2015 Jan25135169
Fast extraction and dilution flow injection mass spectrometry method forquantitative chemical residue screening in food.J Agric Food Chem2011 Jul 2721388127
Effects of exposure to oxamyl, carbofuran, dichlorvos, and lindane on acetylcholinesterase activity in the gills of the Pacific oyster Crassostrea gigas.Environ Toxicol2010 Aug19449386
Cumulative risk assessment of the exposure to organophosphorus and carbamateinsecticides in the Dutch diet.Food Chem Toxicol2008 Sep18652871
Nontarget deposition and losses of oxamyl in surface runoff from flatwoods citrusproduction areas.Environ Toxicol Chem2007 Feb17713205
[Behavior of N-methylcarbamate pesticides during refinement processing of edible oils].J Oleo Sci200717898465
Survey of carbamate and organophosphorous pesticide export from a south Florida(U.S.A.) agricultural watershed: implications of sampling frequency on ecologicalrisk estimation.Environ Toxicol Chem2006 Nov17089706
Susceptibility of pest Nezara viridula (Heteroptera: Pentatomidae) and parasitoid Trichopoda pennipes (Diptera: Tachinidae) to selected insecticides.J Econ Entomol2006 Jun16813294
High-performance liquid chromatography multiresidue method for the determination of N-methyl carbamates in fruit and vegetable juices.J Food Prot2004 Nov15553643
Comparison of susceptibility of pest Euschistus servus and predator Podisus maculiventris (Heteroptera: Pentatomidae) to selected insecticides.J Econ Entomol2004 Jun15279256
N-methyl carbamate concentrations and dietary intake estimates for apple and grape juices available on the retail market in Canada.Food Addit Contam2004 Jun15204533
A simple and rapid assay for analyzing residues of carbamate insecticides invegetables and fruits: hot water extraction followed by liquidchromatography-mass spectrometry.J Agric Food Chem2004 Feb 2514969513
[Utilization of school lunch dietary data to estimate theoretical maximum dailyintake (TMDI) of selected pesticide residues].Nihon Eiseigaku Zasshi2003 Sep14533567
Investigation of alternatives to methyl bromide for management of Meloidogynejavanica on greenhouse grown tomato.Pest Manag Sci2003 Dec14667053
Analyte stability study of N-methylcarbamate pesticides in beef and poultry livertissues by liquid chromatography.J AOAC Int1993 Nov-Dec8286970
Simplified multiresidue method for liquid chromatographic determination ofN-methyl carbamate insecticides in fruits and vegetables.J Assoc Off Anal Chem1988 May-Jun3391959