Oxamyl
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Basic Info
Common Name | Oxamyl(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 ID | F04017 |
CAS Number | 23135-22-0 |
PubChem CID | 9595287 |
Formula | C7H13N3O3S |
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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic acids and derivatives |
Class | Carboxylic acids and derivatives |
Subclass | Carboxylic acid derivatives |
Intermediate Tree Nodes | Carboxylic acid amides |
Direct Parent | Tertiary carboxylic acid amides |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
Substituents | Tertiary 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 |
Description | This 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 Name | Property Value |
---|---|
Molecular Weight | 219.259 |
Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 5 |
Rotatable Bond Count | 4 |
Complexity | 253 |
Monoisotopic Mass | 219.068 |
Exact Mass | 219.068 |
XLogP | -0.5 |
Formal Charge | 0 |
Heavy Atom Count | 14 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 1 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.8602 |
Human Intestinal Absorption | HIA+ | 0.9781 |
Caco-2 Permeability | Caco2- | 0.5386 |
P-glycoprotein Substrate | Non-substrate | 0.8077 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.7604 |
Non-inhibitor | 0.9019 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9574 |
Distribution | ||
Subcellular localization | Mitochondria | 0.6094 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7995 |
CYP450 2D6 Substrate | Non-substrate | 0.8506 |
CYP450 3A4 Substrate | Non-substrate | 0.6053 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.6689 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.7719 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.8991 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.6946 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9556 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9588 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9921 |
Non-inhibitor | 0.9361 | |
AMES Toxicity | AMES toxic | 0.6264 |
Carcinogens | Carcinogens | 0.6196 |
Fish Toxicity | High FHMT | 0.9584 |
Tetrahymena Pyriformis Toxicity | Low TPT | 0.6445 |
Honey Bee Toxicity | High HBT | 0.7987 |
Biodegradation | Not ready biodegradable | 0.9422 |
Acute Oral Toxicity | I | 0.8436 |
Carcinogenicity (Three-class) | Non-required | 0.6989 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | 0.0472 | LogS |
Caco-2 Permeability | 1.0480 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 4.0988 | LD50, mol/kg |
Fish Toxicity | 0.7065 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.1131 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Cashew nuts | 0120030 | European Union | 0.01* | 14/08/2014 | |
Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 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 ... | 0120090 | European Union | 0.01* | 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... | 0161050 | European Union | 0.01* | 14/08/2014 | |
Spring onions/green onions and Welsh onions (Tree onions/Egyptian walking onions, Green garlic,) | 0220040 | European Union | 0.01* | 14/08/2014 | |
Tomatoes (Alkekengi/Chinese lanterns/ground cherries, Cape gooseberries, Cherry tomatoes, Dwarf Cape gooseberries/strawberry tomatoes, Gojiberries/wolfberries, Gojiberries/wolfberries, Litchi tomat... | 0231010 | European Union | 0.01* | 14/08/2014 | |
(c) grape leaves and similar species (Climbing wattle/acacia shoots, Malabar nightshades,) | 0253000 | European Union | 0.01* | 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... | 0256030 | European Union | 0.02* | 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... | 0256080 | European Union | 0.02* | 14/08/2014 | |
Algae and prokaryotes organisms (Carrageen mosses/Irish mosses, Kombu, Spirulina, Spirulina, Other algae, Other procaryotes organisms, Rockweed /knotted kelp,) | 0290000 | European Union | 0.01* | 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... | 0300010 | European Union | 0.01* | 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... | 0632010 | European Union | 0.05* | 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... | 1017000 | European Union | 0.01* | 14/08/2014 | |
FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.01* | 14/08/2014 | |
Citrus fruits | 0110000 | European Union | 0.01* | 14/08/2014 | |
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 14/08/2014 | |
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 14/08/2014 | |
Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 14/08/2014 | |
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 14/08/2014 | |
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.01* | 14/08/2014 |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Chemiluminescent Determination of Oxamyl in Drinking Water and Tomato UsingOnline Postcolumn UV Irradiation in a Chromatographic System. | J Agric Food Chem | 2018 Mar 7 | 29442513 |
Dissipation rate study and pre-harvest intervals calculation of imidacloprid and oxamyl in exported Egyptian green beans and chili peppers after pestigationtreatment. | Food Chem | 2018 Feb 1 | 28946222 |
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 Toxicol | 2016 Mar | 26774911 |
Fenugreek hydrogel-agarose composite entrapped gold nanoparticles foracetylcholinesterase based biosensor for carbamates detection. | Anal Chim Acta | 2015 Jul 30 | 26320646 |
Accelerated biodegradation of selected nematicides in tropical crop soils fromCosta Rica. | Environ Sci Pollut Res Int | 2015 Jan | 25135169 |
Fast extraction and dilution flow injection mass spectrometry method forquantitative chemical residue screening in food. | J Agric Food Chem | 2011 Jul 27 | 21388127 |
Effects of exposure to oxamyl, carbofuran, dichlorvos, and lindane on acetylcholinesterase activity in the gills of the Pacific oyster Crassostrea gigas. | Environ Toxicol | 2010 Aug | 19449386 |
Cumulative risk assessment of the exposure to organophosphorus and carbamateinsecticides in the Dutch diet. | Food Chem Toxicol | 2008 Sep | 18652871 |
Nontarget deposition and losses of oxamyl in surface runoff from flatwoods citrusproduction areas. | Environ Toxicol Chem | 2007 Feb | 17713205 |
[Behavior of N-methylcarbamate pesticides during refinement processing of edible oils]. | J Oleo Sci | 2007 | 17898465 |
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 Chem | 2006 Nov | 17089706 |
Susceptibility of pest Nezara viridula (Heteroptera: Pentatomidae) and parasitoid Trichopoda pennipes (Diptera: Tachinidae) to selected insecticides. | J Econ Entomol | 2006 Jun | 16813294 |
High-performance liquid chromatography multiresidue method for the determination of N-methyl carbamates in fruit and vegetable juices. | J Food Prot | 2004 Nov | 15553643 |
Comparison of susceptibility of pest Euschistus servus and predator Podisus maculiventris (Heteroptera: Pentatomidae) to selected insecticides. | J Econ Entomol | 2004 Jun | 15279256 |
N-methyl carbamate concentrations and dietary intake estimates for apple and grape juices available on the retail market in Canada. | Food Addit Contam | 2004 Jun | 15204533 |
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 Chem | 2004 Feb 25 | 14969513 |
[Utilization of school lunch dietary data to estimate theoretical maximum dailyintake (TMDI) of selected pesticide residues]. | Nihon Eiseigaku Zasshi | 2003 Sep | 14533567 |
Investigation of alternatives to methyl bromide for management of Meloidogynejavanica on greenhouse grown tomato. | Pest Manag Sci | 2003 Dec | 14667053 |
Analyte stability study of N-methylcarbamate pesticides in beef and poultry livertissues by liquid chromatography. | J AOAC Int | 1993 Nov-Dec | 8286970 |
Simplified multiresidue method for liquid chromatographic determination ofN-methyl carbamate insecticides in fruits and vegetables. | J Assoc Off Anal Chem | 1988 May-Jun | 3391959 |