Triazolopyrimidine compounds and their use for controlling pathogenic fungi

A substituted triazolopyrimidine of the formula I

• in which:
• X is halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C2-haloalkoxy;
• W is oxygen or sulfur;
• Y is O—R4 or a group NR5R6;
• A is a chemical bond or a group CR7R8;
• the radicals L independently of one another are halogen, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C1-C6-alkoxy, nitro, amino, NHR, NR2, cyano, S(═O)nA1 or C(═O)A2, in which
• R independently of one another are C1-C8-alkyl or C1-C8-alkylcarbonyl;
• A1 is hydrogen, hydroxyl, C1-C8-alkyl, NH2, 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, hydrogen, hydroxyl, C1-C8-alkyl, NH2, C1-C8-alkylamino or di-(C1-C8-alkyl)amino;
• m is 0 or 1, 2, 3, 4 or 5;
• R1 is hydrogen, C1-C4-alkyl, formyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl or together with R2 is C3-C6-alkylene where 1 carbon atom may be replaced by an oxygen atom or a sulfur atom and which may optionally carry 1, 2, 3 or 4 C1-C4-alkyl groups and/or 1 or 2 radicals Ra;
• Ra:
• is halogen, OH, C1-C4-alkoxy or C1-C4-alkoxycarbonyl;
• R2 is hydrogen, C1-C6-alkyl which may have a radical Rb, C1-C4-haloalkyl, C1-C4-alkoxy, C3-C6-cycloalkyl or phenyl which optionally carries 1, 2 or 3 radicals Rc;
• Rb:
• is OR9, SR10, NR11R12, COOR13, CONR14R15, NHC(═NR16)NR14R15, phenyl which optionally carries 1, 2 or 3 radicals Rc, 5- or 6-membered heteroaryl which has 1 nitrogen atom and if appropriate 1 or 2 further heteroatoms selected from the group consisting of O, S and N as ring members and which optionally carries 1 or 2 radicals Rb or can have a fused-on phenyl ring which for its part can have 1 or 2 radicals Rb, or is C3-C6-cycloalkyl;
• Rc:
• is halogen, C1-C4-alkyl, C1-C4-haloalkyl, OH, C1-C4-alkoxy or C1-C4-alkoxycarbonyl;
• R3 is hydrogen, C1-C4-alkyl or C1-C4-alkoxy or together with R2 is C2-C6-alkylene where 1 carbon atom may be replaced by an oxygen atom or a sulfur atom and which may optionally carry 1, 2, 3 or 4 C1-C4-alkyl groups and/or 1 or 2 radicals Ra;
• R4 is hydrogen, C1-C8-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-halocycloalkyl, C3-C8-cycloalkenyl, phenyl, phenyl-C1-C4-alkyl, where phenyl in the two last-mentioned radicals may have 1, 2 or 3 of the substituents Rd below:
• Rd:
• is halogen, cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylamino, C1-C4-dialkylamino, C1-C4-alkylcarbonyl, C1-C4-alkylsulfonyl, C1-C4-alkylsulfinyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyloxy, C1-C4-alkylaminocarbonyl, C1-C4-dialkylaminocarbonyl,
• or R4 together with one of the radicals R1, R2, R3 or R7 is C2-C6-alkylene where 1 carbon atom may be replaced by an oxygen atom or a sulfur atom and which may optionally carry 1, 2, 3 or 4 radicals selected from the group consisting of halogen and C1-C4-alkyl and/or 1 or 2 radicals Ra;
• R5, R6 independently of one another are hydrogen, C1-C8-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, or together with the nitrogen atom to which they are attached form a saturated 5-, 6- or 7-membered nitrogen heterocycle which optionally has a further heteroatom selected from the group consisting of O, S and N as ring member and which optionally carries 1, 2, 3 or 4 C1-C4-alkyl groups;
• or one of the radicals R5 or R6 together with one of the radicals R1, R2, R3 or R7 is C2-C6-alkylene where 1 carbon atom may be replaced by an oxygen atom or a sulfur atom and which may optionally carry 1, 2, 3 or 4 radicals selected from the group consisting of halogen and C1-C4-alkyl and/or 1 or 2 radicals Ra;
• R7, R8 independently of one another are hydrogen, C1-C4-alkyl or C1-C4-alkoxy or one of the radicals R7 or R8 together with one of the radicals R1 or R2 is C2-C6-alkylene where 1 carbon atom may be replaced an oxygen atom or a sulfur atom and which may optionally carry 1, 2, 3 or 4 C1-C4-alkyl groups and/or 1 or 2 radicals Ra;
• R9 is hydrogen, C1-C8-alkyl, formyl or C1-C8-alkylcarbonyl;
• R10 is hydrogen or C1-C4-alkyl;
• R11, R12 independently of one another are hydrogen, C1-C8-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, or together with the nitrogen atom to which they are attached form a saturated 5-, 6- or 7-membered nitrogen heterocycle which optionally has a further heteroatom selected from the group consisting of O, S and N as ring member and which optionally carries 1, 2, 3 or 4 C1-C4-alkyl groups, where one of the radicals R11, R12 may also be formyl, C1-C8-alkylcarbonyl or C1-C8-alkylthiocarbonyl;
• R13 is hydrogen, C1-C8-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-halocycloalkyl, C3-C8-cycloalkenyl, phenyl, phenyl-C1-C4-alkyl, where phenyl in the two last-mentioned radicals may have 1, 2 or 3 of the abovementioned substituents Rd;
• R14, R15 independently of one another are hydrogen, C1-C8-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, or together with the nitrogen atom to which are they attached form a saturated 5-, 6- or 7-membered nitrogen heterocycle which optionally has a further heteroatom selected from the group consisting of O, S and N as ring member and which optionally carries 1, 2, 3 or 4 C1-C4-alkyl groups;
• R16 is hydrogen, C1-C2-alkyl or C1-C4-alkoxy;
• or an agriculturally acceptable salt of the compound I.