2-Halofuryl-thienyl-3-carboxamides
View Patent ↗Novel 2-halofuryl/thienyl-3-carboxamides of the formula (I) in which A, Hal, R, M and Z are as defined in the description, a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and also novel intermediates and their preparation.
1. 2-Halofuryl/thienyl-3-carboxamides of the formula (I)
in which
A represents O (oxygen) or S (sulphur),
Hal represents halogen,
R represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl; C 1 -C 6 -haloalkyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl)carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy)carbonyl-C 1 -C 3 -alkyl; halo-(C 1 -C 3 -alkyl)carbonyl-C 1 -C 3 -alkyl, halo-(C 1 -C 3 -alkoxy)carbonyl-C 1 -C 3 -alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (C 1 -C 8 -alkyl)carbonyl, (C 1 -C 8 -alkoxy)carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl)carbonyl, (C 3 -C 8 -cycloalkyl)carbonyl; (C 1 -C 6 -haloalkyl)carbonyl, (C 1 -C 6 -haloalkoxy)carbonyl, (halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl)carbonyl, (C 3 -C 8 -halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; or —C(═O)C(═O)R 1 , —CONR 2 R 3 or —CH 2 NR 4 R 5 ,
R 1 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl; C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
R 2 and R 3 independently of one another each represent hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl; C 1 -C 8 -haloalkyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
R 2 and R 3 furthermore together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl, where the heterocycle optionally contains one or two further non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR 6 ,
R 4 and R 5 independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl; C 1 -C 8 -haloalkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
R 4 and R 5 furthermore together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 to 8 ring atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl, where the heterocycle optionally contains 1 or 2 further non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR 6 ,
R 6 represents hydrogen or C 1 -C 6 -alkyl,
M represents a phenyl which is monosubstituted by R 7 ,
R 7 represents hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl,
Z represents Z 1 , Z 2 , Z 3 or Z 4 , in which
Z 1 represents phenyl which is optionally mono- to pentasubstituted by identical or different substituents W 1 ,
W 1 represents halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 8 carbon atoms;
in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulphinyl or haloalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy having 1 to 6 carbon atoms in the respective hydrocarbon chains, alkenylcarbonyl or alkynylcarbonyl having 2 to 6 carbon atoms in the respective hydrocarbon chains;
cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms;
doubly attached alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl;
Z 2 represents bicycloalkyl or cycloalkyl which is optionally mono- or polysubstituted by identical or different substituents,
Z 3 represents unsubstituted C 2 -C 20 -alkyl or represents C 1 -C 20 -alkyl which is mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulphinyl, haloalkylsulphonyl, haloalkoxy, haloalkylamino, halodialkylamino, —SiR 8 R 9 R 10 and C 3 -C 6 -cycloalkyl, where the cycloalkyl moiety is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl,
Z 4 represents C 2 -C 20 -alkenyl or C 2 -C 20 -alkynyl, each of which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulphinyl, haloalkylsulphonyl, haloalkoxy, haloalkylamino, halo-dialkylamino, —SiR 8 R 9 R 10 and C 3 -C 6 -cycloalkyl, where the cycloalkyl moiety is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl,
R 8 and R 9 independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl or C 1 -C 6 -haloalkyl,
R 10 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -cycloalkyl, or represents in each case optionally substituted phenyl or phenylalkyl.
2. 2-Halofuryl/thienyl-3-carboxamides of the formula (I) according to claim 1 in which
A represents O (oxygen) or S (sulphur),
Hal represents fluorine, chlorine, bromine or iodine,
R represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -cycloalkyl; C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl)carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy)carbonyl-C 1 -C 3 -alkyl; halo-(C 1 -C 3 -alkyl)carbonyl-C 1 -C 3 -alkyl, halo-(C 1 -C 3 -alkoxy)carbonyl-C 1 -C 3 -alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (C 1 -C 6 -alkyl)carbonyl, (C 1 -C 4 -alkoxy)carbonyl, (C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl)carbonyl, (C 3 -C 6 -cycloalkyl)carbonyl; (C 1 -C 4 -haloalkyl)carbonyl, (C 1 -C 4 -haloalkoxy)carbonyl, (halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl)carbonyl, (C 3 -C 6 -halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, or —C(═O)C(═O)R 1 , —CONR 2 R 3 or —CH 2 NR 4 R 5 ,
R 1 represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -cycloalkyl; C 1 -C 4 -haloalkyl, (C 1 -C 4 -haloalkoxy, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
R 2 and R 3 independently of one another each represent hydrogen, C 1 -C 6 -alkyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -cycloalkyl; C 1 -C 4 -haloalkyl, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
R 2 and R 3 furthermore together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 or 6 ring atoms which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl, where the heterocycle optionally contains 1 or 2 further non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR 6 ,
R 4 and R 5 independently of one another represent hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl; C 1 -C 4 -haloalkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
R 4 and R 5 furthermore together with the nitrogen atom to which they are attached form a saturated heterocycle having 5 or 6 ring atoms which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl, where the heterocycle optionally contains 1 or 2 further non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR 6 ,
R 6 represents hydrogen or C 1 -C 4 -alkyl,
M represents
where the bond marked “*” is attached to the amide and the bond marked “#” is attached to the radical Z,
R 7 represents hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl,
Z represents Z 1 , Z 2 , Z 3 or Z 4 , where
Z 1 represents phenyl which is optionally mono- to pentasubstituted by identical or different substituents W 1 ,
W 1 represents halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 8 carbon atoms;
in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulphinyl or haloalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy having 1 to 6 carbon atoms in the respective hydrocarbon chains, alkenylcarbonyl or alkynylcarbonyl having 2 to 6 carbon atoms in the respective hydrocarbon chains;
cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms;
doubly attached alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl;
Z 2 represents cycloalkyl or bicycloalkyl having in each case 3 to 10 carbon atoms and being in each case optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of halogen and/or C 1 -C 4 -alkyl,
Z 3 represents unsubstituted C 2 -C 20 -alkyl or C 1 -C 20 -alkyl which is mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkyl-sulphonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -haloalkylthio, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -haloalkylsulphonyl, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkylamino, halo-di(C 1 -C 6 -alkyl)amino, —SiR 8 R 9 R 10 and C 3 -C 6 -cycloalkyl, where the cycloalkyl moiety is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl,
Z 4 represents C 2 -C 20 -alkenyl or C 2 -C 20 -alkynyl, each of which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -haloalkylthio, C 1 -C 6 -haloalkylsulphinyl, C 1 -C 6 -haloalkylsulphonyl, C 1 -C 6 -haloalkoxy, C 1 -C 6 -haloalkylamino, halo-di(C 1 -C 6 -alkyl)amino, —SiR 8 R 9 R 10 and C 3 -C 6 -cycloalkyl, where the cycloalkyl moiety is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl,
R 8 and R 9 independently of one another represent C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl or C 1 -C 3 -alkylthio-C 1 -C 3 -alkyl,
R 10 represents C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 3 -alkylthio-C 1 -C 3 -alkyl, C 3 -C 6 -cycloalkyl, phenyl or benzyl.
3. Process for preparing the 2-halofuryl/thienyl-3-carboxamides of the formula (I) according to claim 1 , characterized in that
a) carboxylic acid derivatives of the formula (II)
in which
A and Hal are as defined in claim 1 and
X 1 represents halogen or hydroxyl
are reacted with aniline derivatives of the formula (III)
in which R, M and Z are as defined in claim 1 ,
optionally in the presence of a catalyst, optionally in the presence of a condensing agent, optionally in the presence of an acid binder and optionally in the presence of a diluent, or
b) halocarboxamides of the formula (IV)
in which
A, Hal, R and M are as defined in claim 1 ,
X 2 represents bromine, iodine or trifluoromethylsulphonate,
are reacted with boronic acid derivatives of the formula (V)
in which
Z 1 is as defined in claim 1 and
G 1 and G 2 each represent hydrogen or together represent tetramethylethylene,
in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent, or
c) boronic acid derivatives of the formula (VI)
in which
A, Hal, R and M are as defined in claim 1 ,
G 3 and G 4 each represent hydrogen or together represent tetramethylethylene
are reacted with phenyl derivatives of the formula (VII)
x 3 -z 1 (VII)
in which
Z 1 is as defined in claim 1 and
X 3 represents chlorine, bromine, iodine or trifluoromethylsulphonate,
optionally in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent, or
d) halocarboxamides of the formula (IV)
in which
A, Hal, R and M are as defined in claim 1 ,
X 2 represents bromine, iodine or trifluoromethylsulphonate,
are reacted with phenyl derivatives of the formula (VII)
x 3 -z 1 (VII)
in which
Z 1 is as defined in claim 1 and
X 3 represents chlorine, bromine, iodine or trifluoromethylsulphonate,
in the presence of a palladium or nickel catalyst and in the presence of 4,4,4′,4′,5,5,5′5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane, optionally in the presence of an acid binder and optionally in the presence of a diluent, or
e) 2-halofuryl/thienyl-3-carboxamides of the formula (I-a)
in which
A, Hal, R and M are as defined in claim 1 ,
X 4 represents C 2 -C 20 -alkenyl or C 2 -C 20 -alkynyl which are in each case optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulphinyl, haloalkylsulphonyl, haloalkoxy, haloalkylamino, halodialkylamino, —SiR 8 R 9 R 10 and C 3 -C 6 -cycloalkyl, where the cycloalkyl moiety is optionally substituted by halogen and/or C 1 -C 4 alkyl,
are hydrogenated, optionally in the presence of a diluent and optionally in the presence of a catalyst, or
f) hydroxyalkylcarboxamides of the formula (VIII)
in which
A, Hal, R and M are as defined in claim 1 ,
X 5 represents C 2 -C 20 -hydroxyalkyl which is optionally additionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulphinyl, haloalkylsulphonyl, haloalkoxy, haloalkylamino, halodialkylamino, —SiR 8 R 9 R 10 and C 3 -C 6 -cycloalkyl, where the cycloalkyl moiety is optionally substituted by halogen and/or C 1 -C 4 -alkyl,
are dehydrated, optionally in the presence of a diluent and optionally in the presence of an acid, or
g) halocarboxamides of the formula (IV)
in which
A, Hal, R and M are as defined in claim 1 ,
X 2 represents bromine, iodine or trifluoromethylsulphonate,
are reacted with an alkyne of the formula (IX)
in which
G 5 represents C 2 -C 18 -alkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulphinyl, haloalkylsulphonyl, haloalkoxy, haloalkylamino, halodialkylamino, —SiR 8 R 9 R 10 and C 3 -C 6 -cycloalkyl, where the cycloalkyl moiety is optionally substituted by halogen and/or C 1 -C 4 -alkyl,
or an alkene of the formula (X)
in which
G 6 , G 7 and G 8 independently of one another each represent hydrogen or alkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulphinyl, haloalkylsulphonyl, haloalkoxy, haloalkylamino, halodialkylamino, —SiR 8 R 9 R 10 and C 3 -C 6 -cycloalkyl, where the cycloalkyl moiety is optionally substituted by halogen and/or C 1 -C 4 -alkyl and the total number of carbon atoms of the open-chain molecular moiety (without substituents) does not exceed the number 20,
optionally in the presence of a diluent, optionally in the presence of an acid binder and optionally in the presence of one or more catalysts, or
h) ketones of the formula (XI)
in which
A, Hal, R and M are as defined in claim 1 ,
G 9 represents hydrogen or C 1 -C 18 -alkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulphinyl, haloalkylsulphonyl, haloalkoxy, haloalkylamino, halodialkylamino, —SiR 8 R 9 R 10 and C 3 -C 6 -cycloalkyl, where the cycloalkyl moiety is optionally substituted by halogen and/or C 1 -C 4 -alkyl,
are reacted with a phosphorus compound of the general formula (XII)
G 10 -Px (XII)
in which
G 10 represents C 1 -C 18 -alkyl which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxy, alkylamino, dialkylamino, haloalkylthio, haloalkylsulphinyl, haloalkylsulphonyl, haloalkoxy, haloalkylamino, halodialkylamino, —SiR 8 R 9 R 10 and C 3 -C 6 -cycloalkyl, where the cycloalkyl moiety is optionally substituted by halogen and/or C 1 -C 4 -alkyl,
Px represents a grouping —P + (C 6 H 5 ) 3 Cl − , —P + (C 6 H 5 ) 3 Br − , —P + (C 6 H 5 ) 3 I − , —P(═O)(OCH 3 ) 3 or —P(═O)(OCH 2 H 5 ) 3 ,
optionally in the presence of a diluent, or
i) 2-halofuryl/thienyl-3-carboxamides of the formula (I-b)
in which
A, Hal, R, M and Z are as defined in claim 1
are reacted with halides of the formula (XIII)
R a —X 6 (XIII)
in which
R a represents C 1 -C 8 -alkyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl; C 1 -C 6 -haloalkyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulphinyl, C 1 -C 4 -haloalkylsulphonyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkyl)carbonyl-C 1 -C 3 -alkyl, (C 1 -C 3 -alkoxy)carbonyl-C 1 -C 3 -alkyl; halo-(C 1 -C 3 -alkyl)carbonyl-C 1 -C 3 -alkyl, halo-(C 1 -C 3 -alkoxy)carbonyl-C 1 -C 3 -alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (C 1 -C 8 -alkyl)carbonyl, (C 1 -C 8 -alkoxy)carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl)carbonyl, (C 3 -C 8 -cycloalkyl)carbonyl; (C 1 -C 6 -haloalkyl)carbonyl, (C 1 -C 6 -haloalkoxy)carbonyl, (halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl)carbonyl, (C 3 -C 8 -halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; or —C(═O)C(═O)R 1 , —CONR 2 R 3 or —CH 2 NR 4 R 5 ,
R 1 , R 2 , R 3 , R 4 and R 5 are as defined above,
X 6 represents chlorine, bromine or iodine,
in the presence of a base and in the presence of a diluent.
4. A composition comprising at least one 2-halofuryl/thienyl-3-carboxamide of the formula (I) according to claim 1 , and one or more extenders and/or surfactants.
5. A method for controlling fungi and bacteria in crop protection, comprising applying at least one 2-halofuryl/thienyl-3-carboxamide of the formula (I) according to claim 1 to fungi, bacteria and/or their habitat.
6. A process for preparing a composition according to claim 4 , comprising mixing at least one 2-halofuryl/thienyl-3-carboxamide of the formula (I) according to claim 1 with extenders and/or surfactants.
7. 2-Halofuryl/thienyl-3-carboxamides of the formula (I) according to claim 1 , in which
R represents hydrogen, and
Z represents Z 1 .
8. 2-Halofuryl/thienyl-3-carboxamides of the formula (I) according to claim 1 , in which
R represents hydrogen, and
Z represents Z 3 .
9. 2-Halofuryl/thienyl-3-carboxamides of the formula (I) according to claim 1 , in which
R represents hydrogen, and
Z represents Z 4 .
10. 2-Halofuryl/thienyl-3-carboxamides of the formula (I) according to claim 1 , in which
R represents hydrogen,
R 7 represents hydrogen or fluorine, and
Z represents Z 3 .
11. 2-Halofuryl/thienyl-3-carboxamides of the formula (I) according to claim 10 , in which
Z 3 represents unsubstituted C 2 -C 20 -alkyl.
12. N-[2-(1,3-dimethylbutyl)phenyl]-2-iodothiophene-3-carboxamide: