7-Aminomethyl-1,2,4-Triazolo[1,5-A]Pyrimidine Compounds And Their Use For Controlling Pathogenic Fungi

A 7-aminomethyl-1,2,4-triazolo[1,5-a]pyrimidine compound of the formula I

• where the index m and the substituents R1, R2, R3, R4, X and L are as defined below:
• R1, R2 independently of one another are hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-alkoxy, C3-C8-cycloalkyl, C5-C10-bicycloalkyl, C3-C8-halocycloalkyl, C2-C8-alkenyl, C4-C10-alkadienyl, C2-C8-haloalkenyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl or phenyl, naphthyl, or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S,
• R1 and R2 together with the nitrogen atom to which they are attached may also form a five- or six-membered heterocyclyl or heteroaryl which is attached via N and may contain one, two or three further heteroatoms from the group consisting of O, N and S as ring members and/or may carry one or more substituents from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy and/or in which two substituents attached to adjacent ring atoms may be C1-C6-alkylene, oxy-C2-C4-alkylene or oxy-C1-C3-alkyleneoxy;
• R1 and/or R2 may carry one, two, three or four identical or different groups Ra:
• Ra is halogen, cyano, nitro, hydroxyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C2-C8-alkenyl, C4-C10-alkadienyl, C2-C8-haloalkenyl, C3-C8-cycloalkenyl, C2-C6-alkenyloxy, C3-C6-haloalkenyloxy, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, C3-C6-cycloalkoxy, C3-C6-cycloalkenyloxy, oxy-C1-C3-alkyleneoxy, phenyl, naphthyl, a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S,
• where the aliphatic, alicylic or aromatic groups in Ra for their part may be partially or fully halogenated or may carry one, two or three groups Rb:
• Rb is halogen, cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, alkyl, haloalkyl, alkenyl, alkadienyl, alkenyloxy, alkynyloxy, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, where the alkyl groups in these radicals contain 1 to 6 carbon atoms and the alkenyl, alkadienyl or alkynyl groups mentioned in these radicals contain 2 to 8 carbon atoms;
• and/or one, two or three of the following radicals:
• cycloalkyl, bicycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy, where the cyclic systems contain 3 to 10 ring members;
• aryl, aryloxy, arylthio, aryl-C1-C6-alkoxy, aryl-C1-C6-alkyl, hetaryl, hetaryloxy, hetarylthio, where the aryl radicals preferably contain 6, 7, 8, 9 or 10 ring members and the hetaryl radicals 5 or 6 ring members, where the cyclic systems may be partially or fully halogenated or substituted by alkyl or haloalkyl groups;
• R3, R4 independently of one another are hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C1-C8-haloalkoxy, C1-C8-alkoxy, C1-C8-haloalkoxy or C1-C8-alkoxy-C1-C8-alkyl, where the 6 lastmentioned radicals may carry one, two, three or four identical or different radicals Rc, where Rc has the meanings given for Ra;
• X is halogen, cyano, a 5- or 6-membered saturated, partially unsaturated or aromatic heterocycle which contains 1, 2 or 3 heteroatoms from the group consisting of O, N and S as ring members, C1-C4-alkyl, C1-C4-alkoxy, C2-C8-alkenyl or C2-C8-alkynyl, where the four lastmentioned radicals may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, C1-C2-alkoxy, C1-C4-alkoxycarbonyl, amino, C1-C4-alkylamino and di-C1-C4-alkylamino and where the 5- or 6-membered heterocycle may carry one or more substituents from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, (exo)-C1-C6-alkylene and oxy-C1-C3-alkyleneoxy;
• L is halogen, cyano, hydroxyl, cyanato (OCN), nitro, C1-C8-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C6-haloalkyl, C2-C10-haloalkenyl, C1-C6-alkoxy, C2-C10-alkenyloxy, C2-C10-alkynyloxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-cycloalkoxy, C1-C8-alkoxycarbonyl, C2-C10-alkenyloxycarbonyl, C2-C10-alkynyloxycarbonyl, aminocarbonyl, C1-C8-alkylaminocarbonyl, di-(C1-C8-)-alkylaminocarbonyl, C1-C8-alkoximinoalkyl, C2-C10-alkenyloximinocarbonyl, C2-C10-alkynyloximinoalkyl, C1-C9-alkylcarbonyl, C2-C10-alkenylcarbonyl, C2-C10-alkynylcarbonyl, C3-C6-cycloalkylcarbonyl, a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms selected from the group consisting of O, N and S, amino, NR5R6, NR5—(C═O)—R6, S(═O)nA1, C(═O)A2, C(═S)A2, a group —C(S)NR7R8, a group —C(═N—OR9)(NR10R11) or a group —C(═N—NR12R13)(NR14R15),
• where
• R5, R6 independently of one another are selected from the group consisting of hydrogen, C1-C6-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C6-cycloalkyl and C3-C6-cycloalkenyl, where the 5 lastmentioned radicals may be partially or fully halogenated or may carry one, two, three or four radicals selected from the group consisting of cyano, C1-C4-alkoximino, C2-C4-alkenyloximino, C2-C4-alkynyloximino and C1-C4-alkoxy;
• A1 is hydrogen, hydroxyl, C1-C8-alkyl, C1-C8-alkylamino or di-(C1-C8-alkyl)amino;
• n is 0, 1 or 2;
• A2 is C2-C8-alkenyl, C1-C8-alkoxy, C1-C6-haloalkoxy, amino or one of the groups mentioned under A1;
• R7, R8, R9, R10, R11, R12, R13, R14 and R15 independently of one another are selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl, where the four lastmentioned radicals may have one, two, three, four, five or six radicals Ra;
• or
• R7 and R8, R10 and R11, R12 and R13 and/or R14 and R15 together with the nitrogen atom to which they are attached form a four-, five- or six-membered saturated or partially unsaturated ring which may carry one, two, three or four substituents independently of one another selected from Ra;
• m is 0, 1, 2, 3, 4 or 5;
• and the agriculturally acceptable salts of the compounds I.