Synthesis and structure-activity study of fungicidal anilinopyrimidines leading to mepanipyrim (KIF-3535) as an anti-Botrytis agent

• Published in: Pest management science Vol. 60; no. 4; pp. 399 - 407
• Main Authors: Nagata, T, Masuda, K, Maeno, S, Miura, I
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.04.2004; Wiley
• Subjects: anilinopyrimidine; antifungal properties; Biological and medical sciences; Botrytis - drug effects; Botrytis cinerea; Chemical control; chemical structure; Control; disease control; Fundamental and applied biological sciences. Psychology; fungal diseases of plants; Fungal plant pathogens; fungicide; Fungicides, Industrial - chemical synthesis; Fungicides, Industrial - toxicity; grey mould; KIF-3535; mepanipyrim; Molecular Structure; new products; pathogenicity; Phytopathology. Animal pests. Plant and forest protection; plant pathogenic fungi; pyrimidine fungicides; Pyrimidines - chemical synthesis; Pyrimidines - toxicity; structure-activity relationships; synthesis; vegetables; Fungicidal effect; Botrytis cinerea; New product; anilinopyrimidine; KIF-3535; Chemical substitution; Fungi; mepanipyrim; Phytotoxicity; Structure activity relation; Chemical control; grey mould; Pyrimidine derivatives; Mould; Fungi Imperfecti; Chemical synthesis; fungicide; Thallophyta
• ISSN: 1526-498X; 1526-4998
• DOI: 10.1002/ps.828

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. Substitutions 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.