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1. WO2012062844 - NOVEL MICROBIOCIDES

Note: Text based on automatic Optical Character Recognition processes. Please use the PDF version for legal matters

[ EN ]

Claims:

1. A compound of formula (I):


wherein

R1 represents hydrogen, halogen, CN, SH, C1-C8 alkylthio, C1-C8 alkylsulphinyl, C1-C8 alkylsulphonyl, NH2, C1-C10 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl,

(R7O)carbonyl(C1-C4 alkyl), phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, NH-C1-C8 alkyl, N(C1-C8 alkyl)2, NO2, OR7, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl and a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms;

A2 represents cycle G-1:


D1 represents N or C-Y1;

D2 represents N or C-Y2;

wherein both D1 and D2 cannot be N;

D3 represents N or C-R6;

D4 represents N or C-R5;

wherein both D3 and D4 cannot be N;

R2, R4, R5 and R6 independently of one another represent hydrogen, halogen, CN, NO2, C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, COR8, OR7, SH, C1-C8 alkylthio, C1-C8

alkylsulphinyl, C1-C8 alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R9)2, CO2R7, O(CO)R8, CON(R9)2, NR9COR8 or CR8N-OR7, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle are optionally substituted by one or more groups

independently selected from halogen, CN, NH2, NO2, OR7, C1-C4 alkyl, C1-C4 haloalkyl;

or R4 and R5, R5 and R2, or R6 and R2 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R9), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by R4 and R5, R5 and R2, or R6 and R2 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, NO2, OH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

X represents X-2, X-3, X-4 or X-5:





Z1, Z2, Z3, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z13 and Z14 independently of one another represent

CR10R11, C=O or C=CR12R13;

Z4 and Z12 represent CR14R15, SiR16R17, C=O or C=CR12R13;

or in each case two adjacent radicals Z4 and Z5 or Z7 and Z8 or Z8 and Z9 or Z11 and Z12 or Z12 and Z13 or Z13 and Z14 may together represent a group selected from CR10=CR11- and -C≡C-, wherein X-4 or X-5 may not contain more than one such group;

each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH, C1-C4 alkyl, C1-C4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

or R10 and R11 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group;

each R12 and R13 independently of one another represent hydrogen, halogen, C1-C4 alkyl or C1-C4 haloalkyl;

each R14, R15, R16 and R17 independently of one another represent hydrogen, halogen,

CN, OH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

or R14 and R15 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group;

wherein the groupings X-2, X-3, X-4 and X-5 contain at most one ring which contains either only one of the radicals Z1 to Z14 or two radicals Z1 to Z14 or three radicals Z1 to Z14 or four radicals Z1 to Z14 as ring members; and wherein radicals Z1, Z3, Z6 and Z10 are not substituted by OH; and wherein none of Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z12, Z13 and Z14 represent a carbon atom substituted by two OH;

Y1, Y2 and Y3 independently of one another represent hydrogen, halogen, CN, NO2, C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, COR8, OR7, SH, C1-C8 alkylthio, C1-C8 alkylsulphinyl, C1-C8 alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R9)2, CO2R7, O(CO)R8, CON(R9)2, NR9COR8 or CR8N-OR7, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, and heterocycle are optionally substituted by one or more groups independently selected from halogen, CN, NH2, NO2, OR7, C1-C4 alkyl and C1-C4 haloalkyl;

or Y1 and Y3, or Y2 and Y3 together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R9), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y1 and Y3, or Y2 and Y3 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, NO2, OH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

A1 represents cycle A-1, A-2, A-3, A-4, A-5, A-6 or A-7:








R18, R19, R20, R21 and R22 independently of one another represent hydrogen, halogen, CN, NO2, C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C2-C8 alkynyl, phenyl, a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, benzyl, COR8, OR7, SH, C1-C8 alkylthio, C1-C8 alkylsulphinyl, C1-C8 alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, N(R9)2, CO2R7, O(CO)R8, CON(R9)2, NR9COR8 or CR8N-OR7, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, heterocycle and benzyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, NO2, OR7, C1-C4 alkyl, C1-C4 haloalkyl;

or R18 and R21, R18 and R22, or R20 and R21 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R9), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by R18 and R21, R18 and R22, or R20 and R21 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, NO2, OH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

when A1 is A-1 and D1 is C-Y1, then R22 and Y1 together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R9), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by R22 and Y1 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, NO2, OH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;

each R7 independently of one another represents hydrogen, C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 alkenyl, C3-C8 alkynyl, C1-C4 alkylsulphonyl, phenyl, benzyl or a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and heterocycle are optionally substituted by one or more groups

independently selected from halogen, CN, NH2, NO2, OH, C1-C4 alkyl, C1-C4-haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4-alkyl-C1-C4-alkoxy and C1-C4-alkoxy-C1-C4-alkyl;

each R8 independently of one another represents hydrogen, C1-C8 alkyl, C3-C8 cycloalkyl,

C2-C8 alkenyl, C2-C8 alkynyl, phenyl, benzyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, NO2, OH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

each R9 independently of one another represents hydrogen, OH, C1-C8 alkyl, C1-C8 alkoxy, C1-C8-alkoxy-C1-C4-alkyl, C3-C8 alkenyl, C3-C8 alkynyl, or COR8, wherein the alkyl, alkoxy, alkenyl and alkynyl are optionally substituted by one or more halogen;

wherein when two radicals R9 are attached to the same nitrogen atom, these radicals can be identical or different;

wherein when two radicals R9 are attached to the same nitrogen atom, both of these radicals cannot be OH, C1-C4 alkoxy or C1-C4 haloalkoxy;

and wherein when two radicals R9 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B-2, B-3, B-4, B-5, B-6, B-7 or B-8:









wherein the cycle formed is optionally substituted by one or more groups independently selected from halogen, CN, NH2, NO2, OH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy; or a salt or N-oxide thereof.

2. A compound according to claim 1, wherein

R1 represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, phenyl, pyridyl, or (R7O)carbonyl(C1-C4 alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, OR7, NH2, NH-C1-C8 alkyl, N(C1-C8 alkyl)2, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl and pyridyl;

D1 represents N or C-Y1;

D2 represents C-Y2;

D3 represents N or C-R6;

D4 represents C-R5;

R2, R4, R5 and R6 independently of one another represent hydrogen, halogen, CN, OR7, C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, phenyl, pyridyl, N(R9)2, CO2R7, NR9COR8, SH, C1-C8 alkylthio, C1-C8 alkylsulphinyl, C1-C8 alkyl sulphonyl, phenylthio, phenylsulphinyl or

phenylsulphonyl, wherein the alkyl, alkenyl, cycloalkyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, OR7, C1-C4 alkyl and C1-C4 haloalkyl;

or R4 and R5, R5 and R2, or R2 and R6, together with the fragment of the pyridyl ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R9), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, wherein the ring formed by R4 and R5, R5 and R2, or R2 and R6 is optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

X represents X-3 or X-5;

Z3, Z5, Z10, Z11, Z13 and Z14 independently of one another represent CR10R11 or

C=CR12R13;

Z4 and Z12 represent CR14R15 or C=CR12R13;

or in each case two adjacent radicals Z4 and Z5 or Z11 and Z12 or Z12 and Z13 or Z13 and Z14 may together represent a group selected from -CR10=CR11- and -C≡C-, wherein X-3 or X-5 may not contain more than one such group;

each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH, C1-C4 alkyl or C1-C4 haloalkyl;

each R12 and R13 independently of one another represent hydrogen, halogen, C1-C4 alkyl or C1-C4 haloalkyl;

each R14 and R15 independently of one another represent hydrogen, halogen, CN, OH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;

or R14 and R15 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group;

Y1, Y2 and Y3 independently of one another represent hydrogen, halogen, CN, OR7, C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, phenyl, pyridyl, N(R9)2, CO2R7, NR9COR8, SH, C1-C8 alkylthio, C1-C8 alkylsulphinyl, C1-C8 alkyl sulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl, wherein the alkyl, alkenyl, cycloalkyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, OR7, C1-C4 alkyl and C1-C4 haloalkyl;

A1 represents cycle A-1, A-2, A-3, A-4, A-5, A-6 or A-7;

R18, R19, R20, R21 and R22 independently of one another represent hydrogen, halogen, CN, OR7, C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, phenyl, pyridyl, benzyl, N(R9)2, CO2R7, NR9COR8, SH, CR8N-OR7, C1-C8 alkylthio, C1-C8 alkylsulphinyl, C1-C8 alkyl sulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl, wherein the alkyl, alkenyl, cycloalkyl, phenyl, pyridyl and benzyl are optionally substituted by one or more groups independently selected from halogen, CN, OR7, C1-C4 alkyl and C1-C4 haloalkyl;

each R7 independently of one another represents hydrogen, C1-C8 alkyl, C1-C8 haloalkyl, C3-C8 alkenyl, C3-C8 alkynyl, C3-C8 haloalkenyl, C3-C8 haloalkynyl, C1-C4 alkylsulphonyl, C1-C4 haloalkylsulphonyl, phenyl, benzyl or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH2, NO2, OH, C1-C4 alkyl, C1-C1-haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

each R8 independently of one another represents hydrogen, C1-C8 alkyl or C1-C8 haloalkyl;

each R9 independently of one another represents hydrogen, C1-C8 alkyl or COR8;

wherein when two radicals R9 are attached to the same nitrogen atom, these radicals can be identical or different;

and wherein when two radicals R9 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl.

3. A compound according to claim 1, wherein

R1 represents hydrogen, C1-C4 alkyl, C2-C4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, OH, NH2, NH-C1-C4 alkyl, N(C1-C4 alkyl)2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl;

D1 represents N or C-Y1;

D2 represents C-Y2;

D3 represents N or C-R6;

D4 represents C-R5;

R2, R4, R5 and R6 independently of one another represent hydrogen, halogen, OR7, CN, C1-C4 alkyl, C3-C6 cycloalkyl, N(R9)2, phenyl, CO2R7 or NR9COR8, wherein the alkyl, cycloalkyl and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4-haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

or R4 and R5, R5 and R2, or R2 and R6, together with the fragment of the pyridyl ring to which they are attached may form a fully or partially unsaturated 5- or 6-membered

carbocyclic ring, optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl;

X represents X-3;

Z3 and Z5 independently of one another represent CR10R11 or C=CR12R13;

Z4 represents CR14R15 or C=CR12R13;

or Z4 and Z5 together represent a group selected from -CR10=CR11- and -C≡C-;

each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH, C1-C4 alkyl or C1-C4 haloalkyl;

each R12 and R13 independently of one another represent hydrogen, halogen, C1-C4 alkyl or C1-C4 haloalkyl;

each R14 and R15 independently of one another represent hydrogen, halogen, CN, OH, C1-C4 alkyl, C1- C4 alkoxy,C1-C4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;

or R14 and R15 together with the carbon atom to which they are attached may form a C3- C6 cycloalkyl group or a C3-C6 halocycloalkyl group;

wherein at least two of Z3, Z4 and Z5 are substituted only by hydrogen or Z4 and Z5 together represent -C≡C-;

Y1, Y2 and Y3 independently of one another represent hydrogen, halogen, OR7, CN, C1-C4 alkyl, C3-C6 cycloalkyl, N(R9)2, phenyl, CO2R7 or NR9COR8, wherein the alkyl, cycloalkyl and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4-haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

A1 represents cycle A-1, A-2 or A-4;

R18, R20, R21 and R22 independently of one another represent hydrogen, halogen, OR7, CN, C1-C4 alkyl, C3-C6 cycloalkyl, N(R9)2, C1-C4 alkylthio, C1-C4 alkylsulphinyl, C1-C4

alkylsulphonyl, phenyl, benzyl, CO2R7, CR8N-OR7 or NR9COR8, wherein the alkyl, cycloalkyl, phenyl and benzyl are optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4-haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

each R7 independently of one another represents hydrogen, C1-C8 alkyl, C1-C8 haloalkyl, C3-C8 alkenyl, C3-C8 haloalkenyl, C3-C8 alkynyl, C3-C8 haloalkynyl, C1-C4 alkylsulphonyl, C1-C4 haloalkylsulphonyl, phenyl, benzyl, or pyridyl, wherein the phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4-haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

each R8 independently of one another represents hydrogen, C1-C4 alkyl or C1-C4 haloalkyl;

each R9 independently of one another represents hydrogen or C1-C4 alkyl;

wherein when two radicals R9 are attached to the same nitrogen atom, these radicals can be identical or different;

and wherein when two radicals R9 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B-2, B-3, B-4 or B-5 wherein the cycle formed is optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl.

4. A compound according to claim 1, wherein

R1 represents hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl or pyridin-2-yl, wherein the phenyl and pyridin-2-yl are optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;

D1 represents C-Y1;

D2 represents C-Y2;

D3 represents C-R6;

D4 represents C-R5;

R2, R4, R5 and R6 independently of one another represent hydrogen, halogen, OH, CN, C1-C4 alkyl, C1-C4 alkoxy, C3-C6 alkenyloxy, C3-C6 cycloalkyl, N(R9)2, phenyl or CO2R7, wherein the alkyl, alkoxy, alkenyloxy, cycloalkyi and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4-haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

or R4 and R5, R5 and R2, or R2 and R6, together with the fragment of the pyridyl ring to which they are attached may form a fully or partially unsaturated 6-membered carbocyclic ring optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl;

X represents X-3;

Z3 and Z5 independently of one another represent CR10R11 or C=CR12R13;

Z4 represents CR14R15 or C=CR12R13;

or Z4 and Z5 together represent a group selected from -CR10=CR11- and -C≡C-;

each R10 and R11 independently of one another represent hydrogen, halogen, CN, OH, C1-C4 alkyl or C1-C4 haloalkyl;

each R12 and R13 independently of one another represent hydrogen, halogen, methyl or halomethyl;

each R14 and R15 independently of one another represent hydrogen, halogen, CN, OH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;

or R14 and R15 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C3-C6 halocycloalkyl group;

wherein at least two of Z3, Z4 and Z5 are substituted only by hydrogen or Z4 and Z5 together represent -C≡C-;

Y1, Y2, and Y3 independently of one another represent hydrogen, halogen, OH, CN, C1-C4 alkyl, C1-C4 alkoxy, C3-C6 alkenyloxy, C3-C6 cycloalkyl, N(R9)2, phenyl or CO2R7, wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4-haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

A1 represents cycle A-1, A-2 or A-4;

R18, R20, R21 and R22 independently of one another represent hydrogen, halogen, OH, CN, C1-C4 alkyl, C1-C4 alkoxy, C3-C6 alkenyloxy, C3-C6 cycloalkyl, N(R9)2, C1-C4 alkylthio, C1-C4 alkylsulphinyl, C1-C4 alkyl sulphonyl, phenyl, phenyloxy, benzyl, benzyloxy, CR8N-OR7,or CO2R7, wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl, phenyl and benzyl are optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4-haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;

each R7 independently or one another represents hydrogen, C1-C4 alkyl or C1-C4 haloalkyl;

each R9 independently of one another represents hydrogen or C1-C4 alkyl;

wherein when two radicals R9 are attached to the same nitrogen atom, these radicals can be identical or different;

and wherein when two radicals R9 are attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached may form a cycle B-1, B-2, B-3, B-4 or B-5, wherein the cycle formed is optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl.

5. A compound according to claim 1, wherein R1 represents pyridyl, optionally substituted by one or more groups independently selected from halogen, CN, NH2, NO2, OH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C6 cycloalkyl and a 5- or 6-membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms.

6. A compound according to claim 1, wherein A2 and R1 represent pyridin-2-yl, optionally substituted by one or more groups independently selected from halogen, CN, NH2, NO2, OH, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6 cycloalkyl and a 5 or 6- membered heterocycle containing one to three heteroatoms independently selected from O, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms.

7. A compound according to any one of claims 1 to 3, wherein R1 represents C1-C4 alkyl,

C2-C4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkoxy and C1-C4 haloalkoxy.

8. A compound according to any one of claims 1 to 7, wherein D1 represents C-Y1 and

D2 represents C-Y2.

9. A compound according to any one claims 1 to 8, wherein R2, R4, R5 and R6 independently of one another represent hydrogen, C1-C4 alkyl, CN or C1-C4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkoxy and C1-C4 haloalkoxy.

10. A compound according to any one of claims 1, 2 and 5 to 9, wherein X represents X-3 or X-5.

11. A compound according to any one of claims 1 to 10, wherein X represents X-3.

12. A compound according to any one of claims 1 to 11, wherein

X represents X-3;

Z3 and Z5 represent methylene;

Z4 represents CR14R15 or C=CR12R13;

each R12 and R13 independently of one another represent hydrogen, halogen, methyl or halomethyl;

each R14 and R15 independently of one another represent hydrogen, halogen, CN, OH, C1-C4 alkyl, C1-C4 haloalkyl, C4-C4 alkoxy or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;

or R14 and R15 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group optionally substituted by halogen.

13. A compound according to any one of claims 1 to 12, wherein Y1 and Y2

independently of one another represent hydrogen, halogen, C1-C4 alkyl, CN or C1-C4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkoxy and C1-C4 haloalkoxy.

14. A compound according to any one of claims 1 to 13, wherein Y1, Y2 and Y3 independently of one another represent hydrogen, halogen, C1-C4 alkyl, CN or C1-C4 alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkoxy and C1-C4 haloalkoxy.

15. A compound according to any one of claims 1 to 14, A1 represents A-1, A-2 or A-4.

16. A compound according to any one of claims 1 to 15, A represents A-1 or A-2.

17. A compound according to any one of claims 2-15 wherein when A1 is A-1 and D1 is

C-Y1, then R22 and Y1 together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R9), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by R22 and Y1 is optionally substituted by one or more groups independently selected from halogen, CN, NH2, NO2, OH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio.

18. A compound of formula (VII)


wherein R28 is a halogen;

A2, R1, X, D1, D2 and Y3 are as defined for a compound of formula (I) in any one of claims 1 to 17; or a salt or N-oxide thereof;

or a compound of formula (IX)


wherein A2, R1, X, D1, D2 and Y3 are as defined for a compound of formula (I) in any one of claims 1 to 17; or a salt or N-oxide thereof;

or a compound of formula (X)


wherein A2, R1, X, D1, D2 and Y3 are as defined for a compound of formula (I) in any one of claims 1 to 17; or a salt or N-oxide thereof;

or a compound of formula (XI)


wherein A2, R1, X, D1, D2 and Y3 are as defined for a compound of formula (I) in any one of claims 1 to 17; or a salt or N-oxide thereof;

or a compound of formula (XIII)


wherein A2, R1, X, D1, D2, Y3, and R18 are as defined for a compound of formula (I) in any one of claims 1 to 17; or a salt or N-oxide thereof;

or a compound of formula (XIV)


wherein A2, R1, X, D1, D2, Y3, and R18 are as defined for a compound of formula (I) in any one of claims 1 to 17; or a salt or N-oxide thereof.

19. A compound according to compound (VII) according to claim 18 wherein R28 represents chlorine, bromine or iodine.

20. A fungicidal composition comprising a fungicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 17, optionally comprising at least one additional active ingredient.

21. A method of controlling or preventing phytopathogenic diseases on useful plants or on propagation material thereof, which comprises applying to the useful plants, the locus thereof or propagation material thereof a fungicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 17.