Patent EA-003281-B1 (EA)
Title: 6-(2-halo-4-alkoxyphenyl) triazolopyrimidines with fungicidal effect
Inventor: PFRENGLE WALDEMAR
IPC: A01N43/90
Filed: 1999-03-19
Abstract: 1. A compound of formula I in which R<1> represents a straight chain or branched C1-C6alkyl, C2-C6 alkenyl or C1-C6 haloalkyl; R<1> and R<2> together with the interjacent nitrogen atom represent a heterocyclic ring with 5 or 6 carbon atoms being optionally substituted with one or two C1-C6alkyl groups; R<3> represents a C3-C6alkenyl, C3-C6alkynyl, phenylC1-C6alkyl, C1-C4alkoxy-C1-C4alkyl, di-C1-C4alkoxy-C1-C4alkyl, phenyl or C1-C4haloalkyl group; L<1> represents a hydrogen, fluorine or chlorine atom; L<2> represents a fluorine or chlorine atom, and Hal represents a halogen atom. 2. A compound according to claim 1 in which L<1> and L<2> each represents a fluorine atom. 3. A compound according to claim 1 or claim 2 in which R<2> represents a hydrogen atom. 4. A compound according to any of claims 1 to 3 in which R<1> and R<2> together with the interjacent nitrogen atom represent a heterocyclic ring selected from 4-methylpiperidin-1-yl, 2-methylpiperidin-1-yl, 5,6-dihydro-2H-pyridin-1-yl, 2-ethylpiperidin-1-yl and azepan-1-yl. 5. A compound of formula I according to any of the preceding claims selected from the following: 5-chloro-7-[N-2-(1,1,1-trifluoropropyl)-amino]-6-(2,6-difluoro-4-(2-fluoroethoxy)-phenyl]-[1,2,4]triazolo[1 ,5-a]pyrimidine, 5-chloro-7-[N-2-(1,1,1-trifluoropropyl)-amino]-6-[2,6-difluoro-4-(3-methylbut-2-enyloxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-[N-2-(1,1,1-trifluoropropyl)-amino]-6-[2,6-difluoro-4-(2-methylbut-3-enyloxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-[N-2-(1,1,1-trifluoropropyl)-amino]-6-(2,6-difluoro-4-benzyloxyphenyl)-1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-[N-2-(1,1,1-trifluoropropyl)-amino]-6-{2,6-difluoro-4-[2-(2-ethoxyethoxy)-ethoxy]-phenyl}-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-[N-2-(1,1,1-trifluoropropyl)-amino]-6-[2,6-difluoro-4-[2-(2-methoxyethoxy)-ethoxy]-phenyl}-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-[N-2-(1,1,1-trifluoropropyl)-amino]-6-[2,6-difluoro-4-(2-methoxyethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-[N-2-(1,1,1-trifluoropropyl)-amino]-6-[2,6-difluoro-4-(2-methoxypropoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-[N-2-(1,1,1-trifluoropropyl)-amino]-6-(2,6-difluoro-4-but-2-enyloxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, and 5-chloro-7-[N-2-(1,1,1-trifluoropropyl)-amino]-6-[2,6-difluoro-4-(2,2,2-trifluoroethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine, 6. A process for the preparation of a compound of formula I as defined in any of the preceding claims which comprises treating a compound of formula II in which R<3>, L<1>, L<2> and Hal are as defined in any one of the preceding claims, with an amine of formula III in which R<1> and R<2> are as defined in any one of the preceding claims. 7. A compound of formula II in which R<3>, L<1>, L<2> and Hal are as defined in any one of the preceding claims 8. A compound of formula VII in which R<3>, L<1> and L<2> are as defined in any one of the preceding claims. 9. A fungicidal composition which comprises a carrier, and as active agent, at least one compound of formula I as defined in any of claim 1 to 5. 10. A method of combating fungus at a locus which comprises treating the locus with an effective amount of least one compound of formula I as defined in any of claim 1 to 5. 11. The use as a fungicide of a compound of formula I as defined in any of claim 1 to 5.