Synthesis and anti-oomycete activity of novel quinazolin- and benzothiazol-6-yloxyacetamides: Potent aza-analogs and five-ring analogs of quinoline fungicides.
Novel quinazolin- and benzothiazol-6-yloxyacetamides show excellent in vivo activity against the three economically most important Oomycete pathogens Phytophthora infestans, Plasmopara viticola and Pythium ultimum. They are polar analogs of known quinolin-6-yloxyacetamides, which are not active against the soil-borne damping-off disease caused by Pythium ultimum. The Bogert quinazoline synthesis, an almost forgotten heterocyclization technique, proved to be highly useful for the concise construction of required quinazolin-6-ol building blocks.
Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
Renaud
R
Beaudegnies
Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
Laura
L
Quaranta
Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
Fiona
F
Murphy Kessabi
Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland. Electronic address: clemens.lamberth@syngenta.com.
Clemens
C
Lamberth
Syngenta Crop Protection AG, Chemical Research, Schaffhauserstr. 101, CH-4332 Stein, Switzerland.
Gertrud
G
Knauf-Beiter
Syngenta Ltd, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, United Kingdom.
Torquil
T
Fraser
D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D009868:Oomycetes / Q000187:drug effects*; D010935:Plant Diseases / Q000382:microbiology / Q000517:prevention & control; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000081:Acetamides; D052160:Benzothiazoles; D005659:Fungicides, Industrial; D011799:Quinazolines
Benzothiazole; Crop protection; Fungicide; Heterocycle; Quinazoline