9660. Tridemorph

Nomenclature

CAS number: 24602-86-6
2,6-Dimethyl-4-tridecylmorpholine; N-tridecyl-2,6-dimethylmorpholine; 2,6-dimethyl-4-tridecyltetrahydro-1,4-oxazine.
C19H39NO; mol wt 297.52.
C 76.70%, H 13.21%, N 4.71%, O 5.38%.

Description and references

Prepn: W. Sanne et al., BE 614214; eidem, US 3468885 (1962, 1969 both to BASF); K.-H. Knig et al., Angew. Chem. Int. Ed. 4, 336 (1965). Structure determn of two diastereomers: D. Kost, E. Gurfinkel, J. Chromatogr. 108, 207 (1975). Fungicidal activity: J. Kradel et al., Proc. 5th Brit. Insectic. Fungic. Conf., 16 (1969); in vitro activity comparison of tridemorph and commercial formulation Calixin: A. Kerkenaar, A. A. Sijpesteijn, Pestic. Biochem. Physiol. 12, 124 (1979). Uptake and distribution in barley: E.-H. Pommer et al., Proc. 5th Brit. Insectic. Fungic. Conf., 347 (1969); R. H. Waring, M. S. Wolfe, Pestic. Sci. 6, 169 (1975). Behavior in soil: S. Otto, N. Drescher, Proc. 7th Brit. Insectic. Fungic. Conf., 57 (1973). Metabolic fate in rats: D. R. Hawkins et al., Pestic. Sci. 5, 535 (1974); of Calixin: R. H. Waring, Xenobiotica 4, 717 (1974). Mode of action: A. Kerkenaar et al., Pestic. Biochem. Physiol. 12, 195 (1979). Comparison of toxicity of tridemorph and Calixin: J. Merkle et al., Teratology 29, 259 (1984). Field trials: P. Lakshmanan, S. Mohan, Pesticides 22, 27 (1988).

Chemical structure

Properties

Oil, bp0.7 130-133°; bp1.3 139-142°. nD25 1.4568.

Derivative

Commercial product.

Nomenclature

Calixin (BASF).

Properties

Reaction mixture of C11-C14 4-alkyl-2,6-dimethylmorpholine homologs containing 60-70% of tridemorph.

Use

Systemic agricultural fungicide.