Clethodim
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Basic Info
| Common Name | Clethodim(F05865) |
| 2D Structure | |
| FRCD ID | F05865 |
| CAS Number | 99129-21-2 |
| PubChem CID | 6444391 |
| Formula | C17H26ClNO3S |
| IUPAC Name | 2-[1-[[(E)-3-chloroprop-2-enoxy]amino]propylidene]-5-(2-ethylsulfanylpropyl)cyclohexane-1,3-dione |
| InChI Key | INNPZTGYZSAJFN-ZTVUPKSFSA-N |
| InChI | InChI=1S/C17H26ClNO3S/c1-4-14(19-22-8-6-7-18)17-15(20)10-13(11-16(17)21)9-12(3)23-5-2/h6-7,12-13,19H,4-5,8-11H2,1-3H3/b7-6+,17-14? |
| Canonical SMILES | CCC(=C1C(=O)CC(CC1=O)CC(C)SCC)NOCC=CCl |
| Isomeric SMILES | CCC(=C1C(=O)CC(CC1=O)CC(C)SCC)NOC/C=C/Cl |
| Synonyms |
Centurion 240
Clethodim
99129-21-2
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Clethodim [ISO]
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Vinylogous amides |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Vinylogous amides |
| Alternative Parents | |
| Molecular Framework | Aliphatic homomonocyclic compounds |
| Substituents | Vinylogous amide - Ketone - Cyclic ketone - Thioether - Vinyl chloride - Vinyl halide - Sulfenyl compound - Dialkylthioether - Haloalkene - Chloroalkene - N-organohydroxylamine - Organohalogen compound - Organic nitrogen compound - Carbonyl group - Organic oxygen compound - Organochloride - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Hydrocarbon derivative - Organic oxide - Aliphatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as vinylogous amides. These are organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 359.909 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 9 |
| Complexity | 457 |
| Monoisotopic Mass | 359.132 |
| Exact Mass | 359.132 |
| XLogP | 4.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 23 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| 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+ | 0.7319 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2- | 0.5442 |
| P-glycoprotein Substrate | Non-substrate | 0.5085 |
| P-glycoprotein Inhibitor | Inhibitor | 0.8032 |
| Non-inhibitor | 0.9263 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8321 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6131 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7894 |
| CYP450 2D6 Substrate | Non-substrate | 0.7915 |
| CYP450 3A4 Substrate | Substrate | 0.6146 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5853 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6773 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8244 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5417 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7234 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5520 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7363 |
| Non-inhibitor | 0.7340 | |
| AMES Toxicity | Non AMES toxic | 0.5342 |
| Carcinogens | Non-carcinogens | 0.5849 |
| Fish Toxicity | High FHMT | 0.9978 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9983 |
| Honey Bee Toxicity | High HBT | 0.6685 |
| Biodegradation | Not ready biodegradable | 0.9780 |
| Acute Oral Toxicity | III | 0.6209 |
| Carcinogenicity (Three-class) | Non-required | 0.5243 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.6244 | LogS |
| Caco-2 Permeability | 1.1471 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6417 | LD50, mol/kg |
| Fish Toxicity | 0.8887 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6624 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Pears (Nashi pears/Oriental pears, Wild pears, Ya pears/Chinese white pears,) | 0130020 | European Union | 0.1 | 01/09/2008 | |
| Pistachios | 0120100 | European Union | 0.1 | 01/09/2008 | |
| Prickly pears/cactus fruits (Pitayas/dragon fruits, Red pitayas, Saguaro fruits, Yellow pitayas,) | 0162040 | European Union | 0.1 | 01/09/2008 | |
| Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou... | 0251040 | European Union | 0.5 | 01/09/2008 | |
| Safflower seeds (Milk thistle seeds, Niger seeds,) | 0401110 | European Union | 0.1 | 01/09/2008 | |
| Borage seeds (Corn gromwell seeds, Evening primrose seeds, Honesty seeds, Honesty seeds, Perilla seeds, Purple viper's bugloss seeds,) | 0401120 | European Union | 0.1 | 01/09/2008 | |
| Star apples/cainitos | 0162050 | European Union | 0.1 | 01/09/2008 | |
| Hemp seeds | 0401140 | European Union | 0.1 | 01/09/2008 | |
| Citrus fruits | 0110000 | European Union | 0.1 | 01/09/2008 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.1 | 01/09/2008 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.1 | 01/09/2008 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.1 | 01/09/2008 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.1 | 01/09/2008 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.1 | 01/09/2008 | |
| Others (2) | 0110990 | European Union | 0.1 | 01/09/2008 | |
| Tree nuts | 0120000 | European Union | 0.1 | 01/09/2008 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.1 | 01/09/2008 | |
| Brazil nuts | 0120020 | European Union | 0.1 | 01/09/2008 | |
| Cashew nuts | 0120030 | European Union | 0.1 | 01/09/2008 | |
| Chestnuts | 0120040 | European Union | 0.1 | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Basis of ACCase and ALS inhibitor resistance in Hordeum glaucum Steud. | Pest Manag Sci | 2017 Aug | 27976507 |
| Inheritance of evolved clethodim resistance in Lolium rigidum populations fromAustralia. | Pest Manag Sci | 2017 Aug | 27933726 |
| Dissipation and residues of clethodim and its oxidation metabolites in arape-field ecosystem using QuEChERS and liquid chromatography/tandem massspectrometry. | Food Chem | 2014 Jan 15 | 24054227 |
| Broad resistance to ACCase inhibiting herbicides in a ryegrass population is due only to a cysteine to arginine mutation in the target enzyme. | PLoS One | 2012 | 22768118 |
| Indirect photodegradation of clethodim in aqueous media. byproduct identificationby quadrupole time-of-flight mass spectrometry. | J Agric Food Chem | 2010 Mar 10 | 20128587 |
| Cross-resistance patterns to ACCase-inhibiting herbicides conferred by mutantACCase isoforms in Alopecurus myosuroides Huds. (black-grass), re-examined at therecommended herbicide field rate. | Pest Manag Sci | 2008 Nov | 18537107 |
| Isoflavone, glyphosate, and aminomethylphosphonic acid levels in seeds ofglyphosate-treated, glyphosate-resistant soybean. | J Agric Food Chem | 2003 Jan 1 | 12502430 |
| Determination of clethodim and its oxidation metabolites in crops by liquidchromatography with confirmation by LC/MS. | J AOAC Int | 2001 Jul-Aug | 11501920 |
| LC/MS analysis of cyclohexanedione oxime herbicides in water. | J Agric Food Chem | 2000 Jul | 10898624 |
| Inhibition of ACCase220 and ACCase240 isozymes from sethoxydim-resistant and-susceptible maize hybrids. | J Agric Food Chem | 1999 Jan | 10563889 |