Tridemorph
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Basic Info
| Common Name | Tridemorph(F05631) |
| 2D Structure | |
| Description | Systemic eradicant cereal fungicide Tridemorph is a fungicide. It was developed in the 1960s by the German multinational BASF who sell tridemorph under the trade name Calixin. It is used to control the fungus Erysiphe graminis in cereals, Mycosphaerella species in bananas, and Caticum solmonicolor in tea. Tridemorph is applied onto many crops across the world, but very little data on usage and production is in the public domain. In high doses it has been shown to have teratogenic effects. These effect are manifested in edemas, hemorrhages, hematomas, abnormal development of the brain (hydrocephalia), visceral cranium (micrognathia, cleft palate) and genitourinary system (hydronephrosis), in decreased size of pelvic bones, shoulder girdle, front and hind limbs, etc. (A7934) Tridemorph belongs to the family of Oxazinanes. These are compounds containing an oxazinane moiety, which consists of a saturated aliphatic six-member ring with one oxygen atom, a nitrogen atom, and four carbon atoms. Isomers of oxaphospholane include 1,2-oxazinane, 1,3-oxazinane, and 1,4-oxazinane. |
| FRCD ID | F05631 |
| CAS Number | 81412-43-3 |
| PubChem CID | 32518 |
| Formula | C19H39NO |
| IUPAC Name | 2,6-dimethyl-4-tridecylmorpholine |
| InChI Key | YTOPFCCWCSOHFV-UHFFFAOYSA-N |
| InChI | InChI=1S/C19H39NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-20-16-18(2)21-19(3)17-20/h18-19H,4-17H2,1-3H3 |
| Canonical SMILES | CCCCCCCCCCCCCN1CC(OC(C1)C)C |
| Isomeric SMILES | CCCCCCCCCCCCCN1CC(OC(C1)C)C |
| Synonyms |
BASF 220F
Tridemorph
2,6-DIMETHYL-4-TRIDECYLMORPHOLINE
Calixine
Calixin
24602-86-6
Kalinin
F 220 (fungicide)
Tridemorphe
Kalixin
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Oxazinanes |
| Subclass | Morpholines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Morpholines |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Morpholine - Tertiary aliphatic amine - Tertiary amine - Oxacycle - Azacycle - Ether - Dialkyl ether - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Amine - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 297.527 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 12 |
| Complexity | 222 |
| Monoisotopic Mass | 297.303 |
| Exact Mass | 297.303 |
| XLogP | 6.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 21 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 2 |
| 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+ | 0.9775 |
| Human Intestinal Absorption | HIA+ | 0.9921 |
| Caco-2 Permeability | Caco2+ | 0.7295 |
| P-glycoprotein Substrate | Substrate | 0.6293 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6549 |
| Non-inhibitor | 0.9400 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.5686 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5802 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.9015 |
| CYP450 2D6 Substrate | Substrate | 0.5866 |
| CYP450 3A4 Substrate | Non-substrate | 0.5348 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7218 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9566 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.5782 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7213 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9304 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9505 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Strong inhibitor | 0.7778 |
| Non-inhibitor | 0.7327 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.8131 |
| Fish Toxicity | Low FHMT | 0.9086 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6428 |
| Honey Bee Toxicity | Low HBT | 0.6492 |
| Biodegradation | Not ready biodegradable | 0.8370 |
| Acute Oral Toxicity | III | 0.8244 |
| Carcinogenicity (Three-class) | Non-required | 0.6186 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.7738 | LogS |
| Caco-2 Permeability | 1.2206 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6295 | LD50, mol/kg |
| Fish Toxicity | 2.3432 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.1266 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Milk & Dairy Produce | Britain | 0.05mg/kg | |||
| Radishes | Britain | 0.05mg/kg | |||
| Other Miscellaneous Fruit | Britain | 0.05mg/kg | |||
| Rhubarbs | 0270070 | European Union | 0.01* | 26/04/2013 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 26/04/2013 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 26/04/2013 | |
| 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* | 26/04/2013 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 26/04/2013 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 26/04/2013 | |
| 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* | 26/04/2013 | |
| Others (2) | 0110990 | European Union | 0.01* | 26/04/2013 | |
| Tree nuts | 0120000 | European Union | 0.02* | 26/04/2013 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.02* | 26/04/2013 | |
| Brazil nuts | 0120020 | European Union | 0.02* | 26/04/2013 | |
| Cashew nuts | 0120030 | European Union | 0.02* | 26/04/2013 | |
| Chestnuts | 0120040 | European Union | 0.02* | 26/04/2013 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.02* | 26/04/2013 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.02* | 26/04/2013 | |
| Macadamias | 0120070 | European Union | 0.02* | 26/04/2013 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.02* | 26/04/2013 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Residual behavior and risk assessment of tridemorph in banana conditions. | Food Chem | 2018 Apr 1 | 29120807 |
| Multiresidue pesticide analysis in nutraceuticals from green tea extracts bycomprehensive two-dimensional gas chromatography with time-of-flight massspectrometry. | J Chromatogr A | 2015 May 22 | 25865796 |
| Analyses of pesticide residues in fruit-based baby food by liquidchromatography/electrospray ionization time-of-flight mass spectrometry. | Rapid Commun Mass Spectrom | 2007 | 17551990 |
| Determination of tridemorph and other fungicide residues in fruit samples byliquid chromatography-electrospray tandem mass spectrometry. | J Chromatogr A | 2004 Aug 6 | 15378888 |
| Effect of some sterol-biosynthesis-inhibiting fungicides on the biosynthesis ofpolyisoprenoid compounds in barley seedings. | Steroids | 1989 Mar-May | 2799851 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]