Substituted phenylamidines and the use thereof as fungicides

An amidine of the formula (X);

• in which
• R1 is selected from the group consisting of hydrogen, straight-chain or branched C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl groups, cyclic C3-8-alkyl, C4-8-alkenyl, and C4-8-alkynyl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P, and S;
• and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, and —CONR′2, where R′ may represent hydrogen or a C1-12-alkyl group, —SH, —SR″, where R″ may represent a straight-chain or branched C1-12- alkyl group which may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, and —CONR′2, where R′ has the above meanings;
• —X is a halogen atom;
• R2 is selected from the group consisting of straight-chain or branched C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl groups, cyclic C3-8-alkyl, C4-8-alkenyl, C4-8-alkynyl groups, C5-18-aryl, C7-19-aralkyl, and C7-19-alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P, and S;
• and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, and —CONR′2, where R′ has the above meanings;
• R3 is selected from the group consisting of —CN, —SH, —SR″, —OR″, —(C═O)—R″, straight-chain or branched C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl groups, cyclic C3-8-alkyl, C4-8-alkenyl, C4-8-alkynyl groups, C5-18-aryl, C7-19-aralkyl, and C7-19-alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P, and S;
• and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, and —CONR′2, where R′ and R″ have the above meanings;
• or in which,
• R2 and R3,
• R2 and R1 or
• R1 and R3 together with the atoms to which they are attached or together with further atoms selected from the group consisting of N, O, P, and S may form a four- to seven-membered ring, which for its part may be substituted by one or more X, R′, OR′, SR′, NR′2, SiR′3, COOR′, CN, and CONR′2 groups, where R′ has the above meanings;
• R4 is selected from the group consisting of —X, —CN, —SH, —SR″, —OR″, —(C═O)—R″, straight-chain or branched C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl groups, cyclic C3-8-alkyl, C4-8-alkenyl, C4-8-alkynyl groups, C5-18-aryl, C7-19-aralkyl, and C7-19-alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P, and S;
• and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, and —CONR′2, where R′ and R″ have the above meanings;
• R5 is selected from the group consisting of hydrogen, —X, —CN, —SH, —SR″, —OR″, —(C═O)—R″, straight-chain or branched C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl groups, cyclic C3-8-alkyl, C4-8-alkenyl, C4-8-alkynyl groups, C5-18-aryl, C7-19-aralkyl, and C7-19-alkaryl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P, and S;
• and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, and —CONR′2, where R′ and R″ have the above meanings;
• R6 is selected from the group consisting of hydrogen;
• straight-chain or branched C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl groups, cyclic C3-8-alkyl, C4-8-alkenyl, and C4-8-alkynyl groups, where in the ring system of all of the cyclic groups mentioned above one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, P, and S;
• and all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′2, —SiR′3, —COOR′, —CN, —CONR′2, —SH, and —SR″, where R′ and R″ have the above meanings.