Fungicidal triazolopyrimidines, process for their preparation, their use for combatting fungi and agents comprising them

摘要

5-(Alkyl, alkenyl or alkynyl)-7-(hydrocarbyl or heterocyclyl)-6-phenyl-1,2,4-triazolo[1,5-a]pyrimidines (I) are new. 5-(Alkyl, alkenyl or alkynyl)-7-(hydrocarbyl or heterocyclyl)-6-phenyl-1,2,4-triazolo[1,5-a]pyrimidines of formula (I) are new. [Image] n : 0-5; R : halo, CN, OH or OCN, or alkyl, alkenyl, alkynyl, T', haloalkenyl, OT, alkenyloxy, alkynyloxy, OT', cycloalkyl, cycloalkenyl, cycloalkoxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, CONH 2, mono- or dialkylaminocarbonyl, alkoximinoalkyl, alkenyloximinocarbonyl, alkynyloximinoalkyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl or Het (all optionally partially or completely halogenated and optionally substituted by 1-4 R a); T : 1-6C alkyl; T' : 1-6C haloalkyl; Het : 5-10 membered, saturated, partially unsaturated or aromatic heterocycle containing 1-4 of O, N and/or S heteroatoms; R 11-10C alkyl, alkenyl, alkynyl, 3-12C cycloalkyl, 3-10C cycloalkenyl, phenyl, naphthyl or Het (all optionally partially or completely halogenated and optionally substituted by 1-4 R a); R ahalo, CN, NO 2, OH, T, T', COT, cycloalkyl, OT, OT', COOT, NHT, NT 2, 2-6C alkenyl, 2-6C alkenyloxy, 3-6C alkynyloxy, alkoximino, alkenyloximino, alkynyloximino, aralkoximino, alkynyl, alkynyloxycarbonyl, phenyl, naphthyl or Het (where all aliphatic, alicyclic or aromatic groups are optionally partially or completely halogenated and optionally substituted by 1-3 R aand/or 1-3 R c); R bhalo, CN, NO 2, OH, SH, NH 2, COOH, CONH 2, CSNH 2, T, T', 2-8C alkenyl, 2-8C alkenyloxy, 2-8C alkynyloxy, OT, OT', ST, NHT, NT 2, CHO, COT, SO 2T, SOT, COOT, OCOT, CONHT, CONT 2, CSNHT or CSNT 2; R ccycloalkyl, -O-cycloalkyl, heterocyclyl, -O-heterocyclyl, aryl, -O-aryl, -S-aryl, -O-T-aryl, -T-aryl, heteroaryl, -O-heteroaryl or -S-heteroaryl (where cycloalkyl or heterocyclyl rings are 3-10 membered, aryl rings are preferably 6-10 membered and heteroaryl rings are preferably 5-6 membered; and all rings are optionally partially or completely halogenated and optionally substituted by alkyl or haloalkyl); and R 21-4C alkyl, 2-4C alkynyl or 2-4C alkynyl (all optionally substituted by halo, CN, NO 2, OMe, OEt or 1-4C alkoxycarbonyl; Unless specified otherwise alkyl moieties have 1-8C, alkenyl or alkynyl moieties 2-10C and cycloalkyl or cycloalkenyl moieties 3-6C. Independent claims are also included for: (1) preparation of (I); and (2) dicarbonyl compound intermediates of formula (III), provided that n is not 0 and R 1and R 2are not both Me. [Image] ACTIVITY : Fungicide. 7-Cyclohexyl-5-methyl-6-(2-chloro-6-fluorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine (Ia) at a concentration of 63 ppm gave at least 90 % protection of tomato plants against Alternaria solani. MECHANISM OF ACTION : None given.