Synthesis of new compounds related to the commercial fungicide tricyclazole.
BACKGROUND
Tricyclazole is a commercial fungicide used to control rice blast. As part of re-registration activities, samples of metabolites and process impurities are required. In addition, isotopically labeled tricyclazole samples are also required.


RESULTS
Four new compounds related to tricyclazole are reported. An isotopically labeled sample of tricyclazole was prepared that contained two (15)N atoms and one (13)C atom. Radiolabeled tricyclazole with (14)C at the triazole C3 position was also synthesized. A new process impurity in technical tricyclazole was identified and synthesized. A new metabolite of tricyclazole was identified, independently synthesized and characterized by X-ray crystallography.


CONCLUSIONS
A previously unreported metabolite of tricyclazole has been identified and structurally characterized. In addition, a new process impurity has been identified by independent synthesis. Identification of these new compounds has facilitated the continued registration of this important fungicide.
Dow AgroSciences, Indianapolis, IN 46268, USA.
Jesse L
JL
Balcer
Carl V
CV
DeAmicis
Peter L
PL
Johnson
Jerzy
J
Klosin
Gregory T
GT
Whiteker
C Srinivas
CS
Rao
Donghua
D
Dai
D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D005659:Fungicides, Industrial; D013844:Thiazoles; C041191:tricyclazole