Synthesis and structure-activity study of fungicidal anilinopyrimidines leading to mepanipyrim (KIF-3535) as an anti-Botrytis agent.
A series of 2-anilinopyrimidines was prepared and their fungicidal activities against Botrytis cinerea Pers were examined. The activity fell sharply with any substitution on the anilinobenzene ring. Substituents at the 5-position of the pyrimidine ring greatly reduced the activity. Substituents such as chloro, methoxy, methylamino, methyl or 1-propynyl were well tolerated at the 4- and 6-positions of the pyrimidine ring. Among these substituents, the combination of methyl and 1-propynyl groups was the most favourable. 2-Anilino-4-methyl-6-(1-propynyl)pyrimidine (KIF-3535), which showed excellent activity and no significant phytotoxicity, was finally selected for development and has been given the common name mepanipyrim.
Nagata
Toshihiro
T
K-I Chemical Research Institute Co Ltd, Fukude-cho, Iwata-gun, Shizuoka 437-1213, Japan. t.nagata@ki-chem.co.jp
Masuda
Katsumi
K
Maeno
Shinichiro
S
Miura
Ichiro
I
D020171:Botrytis / Q000187:drug effects*; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000633:toxicity*; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis / Q000633:toxicity*
D005659:Fungicides, Industrial; D011743:Pyrimidines; C104083:mepanipyrim