Fungicidal 5-Alkylamino-6-phenyl-7-halo-triazolopyrimidines

摘要

5-Alkylamino-6-phenyl-7-halo-triazolopyrimidines are new. 5-Alkylamino-6-phenyl-7-halo-triazolopyrimidines of formula (I) are new. [Image] R1> and R2>H, 1-10C alkyl, 2-10C alkenyl, 2-10C alkynyl, 4-10C alkadienyl, 1-10C haloalkyl, 3-8C cycloalkyl, 5-10C bicycloalkyl, phenyl, naphthyl or 5 or 6 membered heterocyclyl or heteroaryl (both containing 1 - 4 nitrogen atoms and one sulfur or oxygen atom) (where all radical optionally halogenated or optionally mono- to tri-substituted with Ra); R1>-N-R2>5 or 6 membered heterocyclic ring containing 1 - 4 nitrogen atoms and one sulfur or oxygen atom (optionally mono- to tri-substituted by Ra); Rahalogen, cyano, nitro, hydroxyl, 1-6C (halo)alkyl, 3-6C cycloalkyl, 1-6C (halo)alkoxy, 1-6C alkylthio, 1-6C alkylamino, di-(1-6C) alkylamino, 2-6C alkenyl, 2-6C alkenyloxy, 2-6C alkynyl, 3-6C alkynyloxy or 1-4C alkylenedioxy (all optionally halogenated); L : H, halo, 1-10C alkyl, 1-10C alkoxy or 1-10C haloalkyl; n : 1 - 5; X : halo. Independent claims are included for the following: (1) Preparation of (I); and (2) 7-Hydroxy compound of formula (III) and 5-amino-7-hydroxy compounds of formula (IV) as intermediate products. [Image] ACTIVITY : Fungicide. Young apple seedlings of the cultivar common were grown in pots to the 4 - 5 leaf stage. These plants were sprayed to run-off with an aqueous suspension, containing the 5-(4-methylpiperid-1-yl)-7-chloro-6-(2-chloro-6-fluorophenyl)-[1,2,4]-triazolo[1,5-alpha ]pyrimidine (IA), prepared from a stock solution containing 5% of (IA), 94% of cyclohexanone and 1% Tween 20 (emulsifier). After the plants had dried (3 - 5 hours), then were inoculated with an aqueous spore suspension of Venturia inequalis. Then the trial plants were immediately transformed to a humid chamber with 22 - 24[deg]C and a relative humidity (RH) of 100% and were cultivated for 2 days. For a period of further 2 weeks a cultivation in a green house followed at 21 - 23[deg]C and a RH of 95%. Then the extent of fungal attack on the leaves was visually assessed as % diseased leaf area. In this test, the plants which had been treated with (IA) (12.5 ppm) showed an infection of 7% where as the untreated plants were infected to 80%. MECHANISM OF ACTION : Inhibitor of fungi.