S-Metolachlor
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Basic Info
| Common Name | S-Metolachlor(F05912) |
| 2D Structure | |
| FRCD ID | F05912 |
| CAS Number | 87392-12-9 |
| PubChem CID | 11140605 |
| Formula | C15H22ClNO2 |
| IUPAC Name | 2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(2S)-1-methoxypropan-2-yl]acetamide |
| InChI Key | WVQBLGZPHOPPFO-LBPRGKRZSA-N |
| InChI | InChI=1S/C15H22ClNO2/c1-5-13-8-6-7-11(2)15(13)17(14(18)9-16)12(3)10-19-4/h6-8,12H,5,9-10H2,1-4H3/t12-/m0/s1 |
| Canonical SMILES | CCC1=CC=CC(=C1N(C(C)COC)C(=O)CCl)C |
| Isomeric SMILES | CCC1=CC=CC(=C1N([C@@H](C)COC)C(=O)CCl)C |
| Synonyms |
S-Metolachlor
(S)-Metolachlor
87392-12-9
S-Metolachlor [ISO]
UNII-1O4NMK7I6H
1O4NMK7I6H
CHEBI:83647
2-Chloro-N-(2-ethyl-6-methylphenyl)-N-[(1S)-2-methoxy-1-methylethyl]acetamide
Acetamide, 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)-, (S)-
alpha-Metolachlor
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Anilides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Anilides |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Anilide - Toluene - Chloroacetamide - Tertiary carboxylic acid amide - Carboxamide group - Carboxylic acid derivative - Dialkyl ether - Ether - Alkyl chloride - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Alkyl halide - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 283.796 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 6 |
| Complexity | 285 |
| Monoisotopic Mass | 283.134 |
| Exact Mass | 283.134 |
| XLogP | 3.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9869 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.6672 |
| P-glycoprotein Substrate | Non-substrate | 0.7740 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8141 |
| Non-inhibitor | 0.6114 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8036 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6953 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7786 |
| CYP450 2D6 Substrate | Non-substrate | 0.7100 |
| CYP450 3A4 Substrate | Substrate | 0.7008 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5158 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8546 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8464 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5706 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5352 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9383 |
| Non-inhibitor | 0.7334 | |
| AMES Toxicity | AMES toxic | 0.5830 |
| Carcinogens | Carcinogens | 0.5584 |
| Fish Toxicity | Low FHMT | 0.5713 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7462 |
| Honey Bee Toxicity | Low HBT | 0.8836 |
| Biodegradation | Not ready biodegradable | 0.9300 |
| Acute Oral Toxicity | III | 0.8066 |
| Carcinogenicity (Three-class) | Non-required | 0.6108 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.7926 | LogS |
| Caco-2 Permeability | 1.6793 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1424 | LD50, mol/kg |
| Fish Toxicity | 0.8201 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3630 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Arrowroots (Lotus roots, Chinese water chestnut,) | 0212040 | European Union | 0.05* | 06/07/2014 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.05* | 06/07/2014 | |
| Citrus fruits | 0110000 | European Union | 0.05* | 06/07/2014 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.05* | 06/07/2014 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.05* | 06/07/2014 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.05* | 06/07/2014 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.05* | 06/07/2014 | |
| Others (2) | 0110990 | European Union | 0.05* | 06/07/2014 | |
| Tree nuts | 0120000 | European Union | 0.05* | 06/07/2014 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.05* | 06/07/2014 | |
| Brazil nuts | 0120020 | European Union | 0.05* | 06/07/2014 | |
| Cashew nuts | 0120030 | European Union | 0.05* | 06/07/2014 | |
| Chestnuts | 0120040 | European Union | 0.05* | 06/07/2014 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.05* | 06/07/2014 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.05* | 06/07/2014 | |
| Macadamias | 0120070 | European Union | 0.05* | 06/07/2014 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.05* | 06/07/2014 | |
| Pistachios | 0120100 | European Union | 0.05* | 06/07/2014 | |
| Walnuts | 0120110 | European Union | 0.05* | 06/07/2014 | |
| Others (2) | 0120990 | European Union | 0.05* | 06/07/2014 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| S-metolachlor promotes oxidative stress in green microalga Parachlorella kessleri - A potential environmental and health risk for higher organisms. | Sci Total Environ | 2018 Oct 1 | 29751315 |
| The influence of natural dissolved organic matter on herbicide toxicity to marine microalgae is species-dependent. | Aquat Toxicol | 2018 May | 29529466 |
| Development of a new ecotoxicological assay using the testate amoeba Euglypha rotunda (Rhizaria; Euglyphida) and assessment of the impact of the herbicide S-metolachlor. | Chemosphere | 2018 Jun | 29525664 |
| Surface runoff and subsurface tile drain losses of neonicotinoids and companionherbicides at edge-of-field. | Environ Pollut | 2017 May | 28209433 |
| Quantification of the fate of mesotrione applied alone or in a herbicide mixture in two Brazilian arable soils. | Environ Sci Pollut Res Int | 2017 Mar | 28188550 |
| Observed volatilization fluxes of S-metolachlor and benoxacor applied on soilwith and without crop residues. | Environ Sci Pollut Res Int | 2017 Feb | 27915427 |
| Adaptive response under multiple stress exposure in fish: From the molecular toindividual level. | Chemosphere | 2017 Dec | 28869847 |
| Comparative toxic responses of male and female lizards (Eremias argus) exposed to (S)-metolachlor-contaminated soil. | Environ Pollut | 2017 Aug | 28494399 |
| Pesticide residue concentration in soil following conventional and Low-Input CropManagement in a Mediterranean agro-ecosystem, in Central Greece. | Sci Total Environ | 2016 Jan 15 | 26406107 |
| Combined effects of pollutants and salinity on embryo-larval development of thePacific oyster, Crassostrea gigas. | Mar Environ Res | 2016 Feb | 26583531 |
| Nature and decomposition degree of cover crops influence pesticide sorption:quantification and modelling. | Chemosphere | 2015 Jan | 25303661 |
| Gas chromatographic determination of pesticide residues in white mustard. | Food Chem | 2015 Apr 15 | 25466117 |
| Leaching of S-metolachlor, terbuthylazine, desethyl-terbuthylazine, mesotrione,flufenacet, isoxaflutole, and diketonitrile in field lysimeters as affected bythe time elapsed between spraying and first leaching event. | J Environ Sci Health B | 2015 | 26252079 |
| Soil surface colonization by phototrophic indigenous organisms, in two contrastedsoils treated by formulated maize herbicide mixtures. | Ecotoxicology | 2014 Nov | 25129149 |
| Comparative study of cytotoxic and genotoxic effects induced by herbicideS-metolachlor and its commercial formulation Twin Pack Gold® in human hepatoma(HepG2) cells. | Food Chem Toxicol | 2013 Dec | 24144947 |
| Enantioselective binding interaction of the metolachlor pesticide enatiomers withbovine serum albumin--a spectroscopic analysis study. | Spectrochim Acta A Mol Biomol Spectrosc | 2012 Nov | 22898111 |
| Biodegradation and mineralization of metolachlor and alachlor by Candidaxestobii. | J Agric Food Chem | 2011 Jan 26 | 21190381 |
| Solute transport in eroded and rehabilitated prairie landforms. 2. Reactivesolute. | J Agric Food Chem | 2009 Aug 26 | 19653695 |
| Dissipation and residue of S-metolachlor in maize and soil. | Bull Environ Contam Toxicol | 2008 May | 18473109 |
| Effect of selected sugar beet herbicides on germination of various Chenopodiumalbum populations. | Commun Agric Appl Biol Sci | 2007 | 18399450 |