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Record Information
Version1.0
Creation Date2014-09-11 05:23:17 UTC
Update Date2016-11-09 01:09:14 UTC
Accession NumberCHEM003895
Identification
Common NameTridemorph
ClassSmall Molecule
DescriptionSystemic 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. (1) 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.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Ether
  • Food Toxin
  • Fungicide
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
N-Tridecyl-2,6-dimethylmorpholineChEBI
2,6-Dimethyl-4-tridecylmorpholineKegg
2,6-Dimethyl-4-tridecyl-morpholineHMDB
2,6-Dimethyl-N-tridecyl-morpholineHMDB
4-Tridecyl-2,6-dimethylmorpholineHMDB
BASF 220FHMDB
CalixinHMDB
CalixineHMDB
Dimethyl-2,6 tridecyl-4 morpholineHMDB
ElbamorphHMDB
F 220 (Fungicide)HMDB
KalininHMDB
KalixinHMDB
N-Tridecyl-2,6-dimethylmorpholinHMDB
TridemorfHMDB
TridemorpheHMDB
Tridemorph, (trans)-isomerMeSH
Tridemorph, (cis)-isomerMeSH
Chemical FormulaC19H39NO
Average Molecular Mass297.519 g/mol
Monoisotopic Mass297.303 g/mol
CAS Registry Number81412-43-3
IUPAC Name2,6-dimethyl-4-tridecylmorpholine
Traditional Namekalinin
SMILESCCCCCCCCCCCCCN1CC(C)OC(C)C1
InChI IdentifierInChI=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
InChI KeyYTOPFCCWCSOHFV-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentMorpholines
Alternative Parents
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
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point< 25 °C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP6.99ALOGPS
logP6.13ChemAxon
logS-6.4ALOGPS
pKa (Strongest Basic)8.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity93.18 m³·mol⁻¹ChemAxon
Polarizability40.91 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-020r-8970000000-10ddc835f5b043e257a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-9799a4d8461c70fcefafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-4890000000-6a7563ffc760f54b0da5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06xx-9510000000-20032a1ff46485ee571dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-afb4a122996174422182View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0190000000-8ce67e1903c8e6897146View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9210000000-7ddceee3114005204dd5View in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031810
FooDB IDFDB008484
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTridemorph
Chemspider ID30142
ChEBI ID83365
PubChem Compound ID32518
Kegg Compound IDC11285
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Shtenberg AI, Zaeva GN, Rysina TZ, Gavrilenko EV: [Teratogenic effect of the fungicide calixin]. Vopr Pitan. 1981 Nov-Dec;(6):55-61.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.