Synthesis and biological activity of a novel fungicide, pyraziflumid

Pyraziflumid was discovered as a novel SDHI fungicide chemically characterized by the 3-(trifluoromethyl)pyrazine-2-carboxamide group. This chemical series showed particularly high fungicidal activities against a broad spectrum of plant diseases in the case of N-(biphenyl-2-yl) as well as N-(1,1,3-t...

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Bibliographic Details
Published in:Journal of Pesticide Science 2017/11/20, Vol.42(4), pp.151-157
Main Authors: Oda, Masatsugu, Furuya, Takashi, Morishita, Yukio, Matsuzaki, Yoshihiro, Hasebe, Motohiro, Kuroki, Nobutaka
Format: Article
Language:English
Subjects:
3-(trifluoromethyl)pyrazine-2-carboxamide
Biological activity
Biphenyl
fungicide
Fungicides
Lead compounds
NNF-0721
Optimization
Organic chemistry
Original
Plant diseases
pyraziflumid
Pyrazine
SDHI
structure-activity relationships
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Summary:Pyraziflumid was discovered as a novel SDHI fungicide chemically characterized by the 3-(trifluoromethyl)pyrazine-2-carboxamide group. This chemical series showed particularly high fungicidal activities against a broad spectrum of plant diseases in the case of N-(biphenyl-2-yl) as well as N-(1,1,3-trimethylindan-4-yl)carboxamides. Various N-(biphenyl-2-yl)pyrazine-2-carboxamides were synthesized, and their structure–activity relationships were studied. The optimization of the fungicidal performance of the series finally led to the identification of pyraziflumid, which could control a wide range of plant diseases. In this report, details of the structure–activity relationships from the lead compound to pyraziflumid are described.
ISSN:1348-589X
1349-0923
DOI:10.1584/jpestics.D17-041