Kresoxim-Methyl
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Basic Info
| Common Name | Kresoxim-Methyl(F06236) |
| 2D Structure | |
| FRCD ID | F06236 |
| CAS Number | 143390-89-0 |
| PubChem CID | 6112114 |
| Formula | C18H19NO4 |
| IUPAC Name | methyl (2E)-2-methoxyimino-2-[2-[(2-methylphenoxy)methyl]phenyl]acetate |
| InChI Key | ZOTBXTZVPHCKPN-HTXNQAPBSA-N |
| InChI | InChI=1S/C18H19NO4/c1-13-8-4-7-11-16(13)23-12-14-9-5-6-10-15(14)17(19-22-3)18(20)21-2/h4-11H,12H2,1-3H3/b19-17+ |
| Canonical SMILES | CC1=CC=CC=C1OCC2=CC=CC=C2C(=NOC)C(=O)OC |
| Isomeric SMILES | CC1=CC=CC=C1OCC2=CC=CC=C2/C(=N\OC)/C(=O)OC |
| Synonyms |
Kresoxim-methyl [ISO]
Kresoxim-Methyl
143390-89-0
Bas 490 F
Bas 490F
HSDB 7020
UNII-0LXZ062TTB
0LXZ062TTB
CHEBI:2962
EINECS Annex I Index 607-310-00-0
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Phenol ethers |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenol ethers |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenoxy compound - Phenol ether - Alkyl aryl ether - Toluene - Monocyclic benzene moiety - Methyl ester - Carboxylic acid ester - Carboxylic acid derivative - Ether - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 313.353 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 7 |
| Complexity | 410 |
| Monoisotopic Mass | 313.131 |
| Exact Mass | 313.131 |
| XLogP | 4.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 23 |
| 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+ | 0.9069 |
| Human Intestinal Absorption | HIA+ | 0.9931 |
| Caco-2 Permeability | Caco2+ | 0.5980 |
| P-glycoprotein Substrate | Non-substrate | 0.6874 |
| P-glycoprotein Inhibitor | Inhibitor | 0.5556 |
| Inhibitor | 0.5851 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7012 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8186 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7522 |
| CYP450 2D6 Substrate | Non-substrate | 0.7922 |
| CYP450 3A4 Substrate | Substrate | 0.6009 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5169 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6499 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8757 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.6711 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.6114 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6800 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9615 |
| Non-inhibitor | 0.8992 | |
| AMES Toxicity | Non AMES toxic | 0.5578 |
| Carcinogens | Non-carcinogens | 0.6748 |
| Fish Toxicity | High FHMT | 0.8926 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9636 |
| Honey Bee Toxicity | High HBT | 0.6617 |
| Biodegradation | Not ready biodegradable | 0.7681 |
| Acute Oral Toxicity | III | 0.7729 |
| Carcinogenicity (Three-class) | Non-required | 0.5546 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.0193 | LogS |
| Caco-2 Permeability | 1.1039 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8285 | LD50, mol/kg |
| Fish Toxicity | 0.3042 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7529 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Currants (black, red and white) | 0154030 | European Union | 0.9 | 26/04/2016 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.5 | 26/04/2016 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.5 | 26/04/2016 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 26/04/2016 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 26/04/2016 | |
| 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* | 26/04/2016 | |
| Others (2) | 0110990 | European Union | 0.01* | 26/04/2016 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.01* | 26/04/2016 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 26/04/2016 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 26/04/2016 | |
| Chestnuts | 0120040 | European Union | 0.01* | 26/04/2016 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 26/04/2016 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.01* | 26/04/2016 | |
| Macadamias | 0120070 | European Union | 0.01* | 26/04/2016 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.05* | 26/04/2016 | |
| Pistachios | 0120100 | European Union | 0.01* | 26/04/2016 | |
| Walnuts | 0120110 | European Union | 0.01* | 26/04/2016 | |
| Others (2) | 0120990 | European Union | 0.01* | 26/04/2016 | |
| Pome fruits | 0130000 | European Union | 0.2 | 26/04/2016 | |
| Apples (Crab apples/wild apples, Tejocotes,) | 0130010 | European Union | 0.2 | 26/04/2016 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| AGRO-2014: A time dependent model for assessing the fate and food-webbioaccumulation of organic pesticides in farm ponds: Model testing andperformance analysis. | Sci Total Environ | 2018 Oct 15 | 29929298 |
| The transfer of active ingredients of insecticides and fungicides from an orchardto beehives. | J Environ Sci Health B | 2018 Jan 2 | 29083963 |
| Dissipation behaviour, residue distribution and dietary risk assessment oftetraconazole and kresoxim-methyl in greenhouse strawberry via RRLC-QqQ-MS/MStechnique. | Ecotoxicol Environ Saf | 2018 Feb | 29195223 |
| Strobilurins as growth-promoting compounds: how Stroby regulates Arabidopsis leafgrowth. | Plant Cell Environ | 2017 Sep | 28444690 |
| Synthesis of 1,2,3-Thiadiazole and Thiazole-Based Strobilurins as PotentFungicide Candidates. | J Agric Food Chem | 2017 Feb 1 | 28055187 |
| Kresoxim-methyl Derivatives: Synthesis and Herbicidal Activities of(Pyridinylphenoxymethylene)phenyl Methoxyiminoacetates. | J Agric Food Chem | 2017 Aug 2 | 28683548 |
| Determination of strobilurin fungicide residues in fruits and vegetables bynonaqueous micellar electrokinetic capillary chromatography with indirectlaser-induced fluorescence. | Electrophoresis | 2017 Aug | 28497571 |
| Residue behavior and dietary intake risk assessment of three fungicides intomatoes (Lycopersicon esculentum Mill.) under greenhouse conditions. | Regul Toxicol Pharmacol | 2016 Nov | 27647629 |
| Kresoxim-methyl primes Medicago truncatula plants against abiotic stress factors via altered reactive oxygen and nitrogen species signalling leading to downstreamtranscriptional and metabolic readjustment. | J Exp Bot | 2016 Mar | 26712823 |
| Influence of the presence of ethanol on in vitro bioavailability of fungicideresidues. | Food Chem Toxicol | 2016 Jul | 27112541 |
| Dissipation of Fungicide Residues during Winemaking and Their Effects onFermentation and the Volatile Composition of Wines. | J Agric Food Chem | 2016 Feb 17 | 26808836 |
| Leaching of the Neonicotinoids Thiamethoxam and Imidacloprid from Sugar Beet SeedDressings to Subsurface Tile Drains. | J Agric Food Chem | 2016 Aug 24 | 27529118 |
| Alterations of cellular redox homeostasis in cultured fibroblast-like renal cellsupon exposure to low doses of cytochrome bc1 complex inhibitor kresoxim-methyl. | Biochem Pharmacol | 2016 Aug 1 | 27265144 |
| Influence of the use of fungicides on the volatile composition of Monastrell red wines obtained from inoculated fermentation. | Food Chem | 2015 Mar 1 | 25306363 |
| Toxicity evaluation of new agricultural fungicides in primary cultured corticalneurons. | Environ Res | 2015 Jul | 25825129 |
| Probabilistic Exposure Assessment for Applicators during Treatment of theFungicide Kresoxim-methyl on an Apple Orchard by a Speed Sprayer. | J Agric Food Chem | 2015 Dec 9 | 26492351 |
| Phenolic compounds and antioxidant activity of red wine made from grapes treated with different fungicides. | Food Chem | 2015 Aug 1 | 25766797 |
| Determination of fungicides in white grape bagasse by pressurized liquidextraction and gas chromatography tandem mass spectrometry. | J Chromatogr A | 2014 May 23 | 24746069 |
| Effect of two anti-fungal treatments (metrafenone and boscalid pluskresoxim-methyl) applied to vines on the color and phenol profile of differentred wines. | Molecules | 2014 Jun 16 | 24936710 |
| Determination of strobilurin fungicide residues in fruits and vegetables bymicellar electrokinetic capillary chromatography with sweeping. | J Chromatogr Sci | 2014 Feb | 23390023 |