Patent EA-002906-B1 (EA)
Title: Triflouromethylalkylamino-triazolopyrimidenes derivatives, process for the preparation thereof, fungicidal composition, use and method of combatting fungus at a locus
Inventor: PEES KLAUS-JIERGEN
IPC: A01N43/90
Filed: 1998-03-23
Abstract: 1. A compound of the general formula I   in which R<1> and R<2> each independently represent a hydrogen atom or an optionally substituted C1-C6 alkyl, C1-C6 haloalkyl or phenyl group, Hal represents a halogen atom L<1> through L<5> each independently represent an hydrogen or halogen atom or an C1-C6 alkyl, C1-C6 alkoxy or nitro group. 2. A compound according to Claim 1 in which at least one of L<1> and L<5> represents a halogen atom. 3. A compound according to Claim 1 or 2 in which R<1> represents hydrogen atom or a methyl group. 4. A compound according to any of the preceding Claims in which R<2> represents a hydrogen or a C1-C6 alkyl group. 5. A compound according to any of the preceding Claims in which at least one of R<1> and R<2> represents a hydrogen atom. 6. The following compounds of formula I: 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4jtriazolo[1,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-7-(2,2,2-trifluoroethylamino)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chlorophenyl)-7-(2,2,2-trifluoroethylamino)- [1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2-fluorophenyl)-7-(2,2,2-trifluoroethylamino)[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-[2-(1,1,1-trifluoro)propylamino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-[2-(1,1,1-trifluoro)propylamino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-[2-(1,1,1-trifluoro)propylamino][1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2-methylphenyl)-7-[2-(1,1,1-trifluoro)propylamino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-fluorophenyl)-7-[2-(1,1,1-trifluoro)propylamino] [1,2,4]triazolo(1,5-a]pyrimidine, 5-chloro-6-(2-chlorophenyl)-7-[2-(1,1,1-trifluoro)propylaminoi- [1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-allylamino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-allylamino][1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2-fluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-allylamino] [1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-allylamino][1,2,4]triazolo[1,5-a]pyrimidine 5-chloro-6-(2-chlorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-allylamino]-[1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2-methylphenyl)-7-[N-(2,2,2-trifluoroethyl)-N-allylamino]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-fluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-ethylamino]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-ethylamino]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-ethylamino][1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-ethylamino] [1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chlorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-ethylamino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-methylphenyl)-7-[N-(2,2,2-trifluoroethyl)-N-ethylamino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-(2methylpropyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-(2-methylpropyl)amino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-fluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-(2-methylpropyl)-amino] [1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-(2methylpropyl)amino]-[1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2-methylphenyl)-7-[N-(2,2,2-trifluoroethyl)-N-(2-methylpropyl)-amino] [1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-fluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-methylamino][1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-methylamino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-methylamino][1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2-methylphenyl)-7-[N-(2,2,2-trifluoroethyl)-N-methylamino] [1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-fluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-isopropylamino]-[1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-isopropylamino][1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-isopropylamino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-isopropylamino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-[N-(2,2,2-trifluoroethyl)-N-(1 -phenylethyl)amino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-fluorophenyl)-7-[N,N-di-(2,2,2-trifluoroethyl)amino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-methylphenyl)-7-[N,N-di-(2,2,2-trifluoroethyl)amino] [1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chlorophenyl)-7-[N,N-di-(2,2,2-trifluoroethyl)amino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-[N,N-di-(2,2,2-trifluoroethyl)amino] [1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-[N,N-di-(2,2,2-trifluoroethyl)amino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-[N,N-di-(2,2,2-trifluoroethyl)amino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-[N,-(2,2,2-trifluoroethyl)-N-(1,2-dimethylpropyl)amino]-[1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-[N,-(2,2,2-trifluoroethyl)-N (trimethylsilylmethyl)amino]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-bromo-5-chlorophenyl)-7-[2-(1,1,1 -trifluoro)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chlorophenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(4-chlorophenyl)-7-(2,2,2-trifluoroethylamino)[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(4-bromophenyl)-7-(2,2,2-trifluoroethylamino) [1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(4-methoxyphenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(4-nitrophenyl)-7-(2,2,2-trifluoroethylamino) [1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-fluorophenyl)-7-(1-phenyl-2,2,2-trifluoroethylamino)[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-[2-(1,1,1-trifluoro)butylamino][1 ,2,4]triazolo[1 ,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(1-phenyl-2,2,2-trifluoroethylamino)[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-fluorophenyl)-7-[2-(1,1,1-trifluoro)butylamino][1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-(1-phenyl-2,2,2-trifluoroethylamino)[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-(1-phenyl-2,2,2-trifluoroethylamino)[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-[2-(1,1,1-trifluoro)butylamino] [1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-[2-(1,1,1-trifluoro)butylamino][1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2-chlorophenyl)-7-[2-(1,1,1-trifluoro)butylamino][1,2,4]triazolo[1,5-a]yrimidine, 5-chloro-6-(2-chlorophenyl)-7-(l -phenyl-2,2,2-trifluoroethylamino) [1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2,4-difluorophenyl)-7-(2,2,2-trifluoroethylamin [1,2,4]triazolo[l,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-[2-(1,1,1-trifluoro)-3-methylbutylamino][1,2,4]triazoio[l,5-a]pyrimidine, 5-chloro-6-(2,6-difluoro-4-methoxyphenyl)-7-[2-(1,1,1-trifluoro)propylamino][1,2,4]triazolo[1,5-a]pyrimidine. 7. A process for the preparation of a compound of formula I as defined in any one of the preceding Claims which comprises treating a compound of the general formula II   in which L<1>through L<5> and Hal are as defined in any one of the preceding Claims; with an amine of the general formula Ill   in which R<1> and R<2> are as defined in any one of the preceding Claims, M is selected from the group comprising hydrogen, Li, Na, K, Zn and Cu to produce a compound of formula I. 8. A fungicidal composition which comprises a carrier, and as active agent, at least one compound of formula I as defined in any one of Claims 1 to 6. 9. A method of combating fungus at a locus which comprises treating the locus with a compound of formula I as defined in any one of Claims 1 to 6 or with a composition as defined in Claim 8. 10. The use as a fungicide of a compound of formula I as defined in any one of Claims 1 to 6 or a composition as defined in Claim 8.