# US 7,745,483 B2 · 2-Halofuryl-thienyl-3-carboxamides

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- Number: US 7,745,483 B2
- Document ID: US7745483B2
- Status: Granted
- Kind: B2
- Application number: 10/588,293
- Filed: 2005-01-22
- Published: 2008-03-13
- Granted: 2010-06-29
- Earliest claimed: 2004-02-06
- Assignees: Bayer CropScience AG
- Inventors: Ralf Dunkel; Hans-Ludwig Elbe; Jörg Nico Greul; Benoit Hartmann; Peter Dahmen; Karl-Heinz Kuck; Ulrike Wachendorff-Neumann
- Web page: https://patentgrep.com/patent/US7745483B2

## CPC

- C07D 307/68: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- A01N 43/08: with oxygen as the ring hetero atom
- A01N 43/10: with sulfur as the ring hetero atom
- A01N 43/40: six-membered rings
- C07D 333/38: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 495/12: in which the condensed system contains three hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

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.

## Claims

### Claim 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, C1-C8-alkyl, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl; C1-C6-haloalkyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1-C3-alkyl; halo-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halo-(C1-C3-alkoxy)carbonyl-C1-C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (C1-C8-alkyl)carbonyl, (C1-C8-alkoxy)carbonyl, (C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C3-C8-cycloalkyl)carbonyl; (C1-C6-haloalkyl)carbonyl, (C1-C6-haloalkoxy)carbonyl, (halo-C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C3-C8-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; or —C(═O)C(═O)R1, —CONR2R3 or —CH2NR4R5,
R1 represents hydrogen, C1-C8-alkyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl; C1-C6-haloalkyl, C1-C6-haloalkoxy, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
R2 and R3 independently of one another each represent hydrogen, C1-C8-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl; C1-C8-haloalkyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
R2 and R3 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 C1-C4-alkyl, where the heterocycle optionally contains one or two further non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR6,
R4 and R5 independently of one another represent hydrogen, C1-C8-alkyl, C3-C8-cycloalkyl; C1-C8-haloalkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
R4 and R5 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 C1-C4-alkyl, where the heterocycle optionally contains 1 or 2 further non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR6,
R6 represents hydrogen or C1-C6-alkyl,
M represents a phenyl which is monosubstituted by R7,
R7 represents hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl,
Z represents Z1, Z2, Z3 or Z4, in which
Z1 represents phenyl which is optionally mono- to pentasubstituted by identical or different substituents W1,
W1 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;
Z2 represents bicycloalkyl or cycloalkyl which is optionally mono- or polysubstituted by identical or different substituents,
Z3 represents unsubstituted C2-C20-alkyl or represents C1-C20-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, —SiR8R9R10 and C3-C6-cycloalkyl, where the cycloalkyl moiety is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C1-C4-alkyl,
Z4 represents C2-C20-alkenyl or C2-C20-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, —SiR8R9R10 and C3-C6-cycloalkyl, where the cycloalkyl moiety is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C1-C4-alkyl,
R8 and R9 independently of one another represent hydrogen, C1-C8-alkyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl or C1-C6-haloalkyl,
R10 represents hydrogen, C1-C8-alkyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, or represents in each case optionally substituted phenyl or phenylalkyl.

### Claim 2 (depends on 1)

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, C1-C6-alkyl, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C6-cycloalkyl; C1-C4-haloalkyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, halo-C1-C3-alkoxy-C1-C3-alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1-C3-alkyl; halo-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halo-(C1-C3-alkoxy)carbonyl-C1-C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (C1-C6-alkyl)carbonyl, (C1-C4-alkoxy)carbonyl, (C1-C3-alkoxy-C1-C3-alkyl)carbonyl, (C3-C6-cycloalkyl)carbonyl; (C1-C4-haloalkyl)carbonyl, (C1-C4-haloalkoxy)carbonyl, (halo-C1-C3-alkoxy-C1-C3-alkyl)carbonyl, (C3-C6-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms, or —C(═O)C(═O)R1, —CONR2R3 or —CH2NR4R5,
R1 represents hydrogen, C1-C6-alkyl, C1-C4-alkoxy, C1-C3-alkoxy-C1-C3-alkyl, C3-C6-cycloalkyl; C1-C4-haloalkyl, (C1-C4-haloalkoxy, halo-C1-C3-alkoxy-C1-C3-alkyl, C3-C6-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
R2 and R3 independently of one another each represent hydrogen, C1-C6-alkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C6-cycloalkyl; C1-C4-haloalkyl, halo-C1-C3-alkoxy-C1-C3-alkyl, C3-C6-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
R2 and R3 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 C1-C4-alkyl, where the heterocycle optionally contains 1 or 2 further non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR6,
R4 and R5 independently of one another represent hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl; C1-C4-haloalkyl, C3-C6-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
R4 and R5 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 C1-C4-alkyl, where the heterocycle optionally contains 1 or 2 further non-adjacent heteroatoms selected from the group consisting of oxygen, sulphur and NR6,
R6 represents hydrogen or C1-C4-alkyl,
M represents
where the bond marked “*” is attached to the amide and the bond marked “#” is attached to the radical Z,
R7 represents hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl,
Z represents Z1, Z2, Z3 or Z4, where
Z1represents phenyl which is optionally mono- to pentasubstituted by identical or different substituents W1,
W1 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;
Z2 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 C1-C4-alkyl,
Z3 represents unsubstituted C2-C20-alkyl or C1-C20-alkyl which is mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkyl-sulphonyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-haloalkylthio, C1-C6-haloalkylsulphinyl, C1-C6-haloalkylsulphonyl, C1-C6-haloalkoxy, C1-C6-haloalkylamino, halo-di(C1-C6-alkyl)amino, —SiR8R9R10 and C3-C6-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, C1-C4-alkyl and C1-C4-haloalkyl,
Z4 represents C2-C20-alkenyl or C2-C20-alkynyl, each of which is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, C1-C6-alkylthio, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-haloalkylthio, C1-C6-haloalkylsulphinyl, C1-C6-haloalkylsulphonyl, C1-C6-haloalkoxy, C1-C6-haloalkylamino, halo-di(C1-C6-alkyl)amino, —SiR8R9R10 and C3-C6-cycloalkyl, where the cycloalkyl moiety is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, C1-C4-alkyl and C1-C4-haloalkyl,
R8 and R9 independently of one another represent C1-C6-alkyl, C1-C6-alkoxy, C1-C3-alkoxy-C1-C3-alkyl or C1-C3-alkylthio-C1-C3-alkyl,
R10 represents C1-C6-alkyl, C1-C6-alkoxy, C1-C3-alkoxy-C1-C3-alkyl, C1-C3-alkylthio-C1-C3-alkyl, C3-C6-cycloalkyl, phenyl or benzyl.

### Claim 3 (depends on 1)

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
X1 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,
X2 represents bromine, iodine or trifluoromethylsulphonate,
are reacted with boronic acid derivatives of the formula (V)
in which
Z1 is as defined in claim 1 and
G1 and G2 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,
G3 and G4 each represent hydrogen or together represent tetramethylethylene
are reacted with phenyl derivatives of the formula (VII)
x3-z1 (VII)
in which
Z1 is as defined in claim 1 and
X3 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,
X2 represents bromine, iodine or trifluoromethylsulphonate,
are reacted with phenyl derivatives of the formula (VII)
x3-z1 (VII)
in which
Z1 is as defined in claim 1 and
X3 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,
X4 represents C2-C20-alkenyl or C2-C20-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, —SiR8R9R10 and C3-C6-cycloalkyl, where the cycloalkyl moiety is optionally substituted by halogen and/or C1-C4 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,
X5 represents C2-C20-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, —SiR8R9R10 and C3-C6-cycloalkyl, where the cycloalkyl moiety is optionally substituted by halogen and/or C1-C4-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,
X2 represents bromine, iodine or trifluoromethylsulphonate,
are reacted with an alkyne of the formula (IX)
in which
G5 represents C2-C18-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, —SiR8R9R10 and C3-C6-cycloalkyl, where the cycloalkyl moiety is optionally substituted by halogen and/or C1-C4-alkyl,
or an alkene of the formula (X)
in which
G6, G7 and G8 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, —SiR8R9R10 and C3-C6-cycloalkyl, where the cycloalkyl moiety is optionally substituted by halogen and/or C1-C4-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,
G9 represents hydrogen or C1-C18-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, —SiR8R9R10 and C3-C6-cycloalkyl, where the cycloalkyl moiety is optionally substituted by halogen and/or C1-C4-alkyl,
are reacted with a phosphorus compound of the general formula (XII)
G10-Px (XII)
in which
G10 represents C1-C18-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, —SiR8R9R10 and C3-C6-cycloalkyl, where the cycloalkyl moiety is optionally substituted by halogen and/or C1-C4-alkyl,
Px represents a grouping —P+(C6H5)3Cl−, —P+(C6H5)3Br−, —P+(C6H5)3I−, —P(═O)(OCH3)3 or —P(═O)(OCH2H5)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)
Ra—X6 (XIII)
in which
Ra represents C1-C8-alkyl, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C8-cycloalkyl; C1-C6-haloalkyl, C1-C4-haloalkylthio, C1-C4-haloalkylsulphinyl, C1-C4-haloalkylsulphonyl, halo-C1-C4-alkoxy-C1-C4-alkyl, C3-C8-halocycloalkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-C1-C3-alkyl, (C1-C3-alkyl)carbonyl-C1-C3-alkyl, (C1-C3-alkoxy)carbonyl-C1-C3-alkyl; halo-(C1-C3-alkyl)carbonyl-C1-C3-alkyl, halo-(C1-C3-alkoxy)carbonyl-C1-C3-alkyl having in each case 1 to 13 fluorine, chlorine and/or bromine atoms; (C1-C8-alkyl)carbonyl, (C1-C8-alkoxy)carbonyl, (C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C3-C8-cycloalkyl)carbonyl; (C1-C6-haloalkyl)carbonyl, (C1-C6-haloalkoxy)carbonyl, (halo-C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C3-C8-halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; or —C(═O)C(═O)R1, —CONR2R3 or —CH2NR4R5,
R1, R2, R3, R4 and R5 are as defined above,
X6 represents chlorine, bromine or iodine,
in the presence of a base and in the presence of a diluent.

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 1, 4)

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.

### Claim 7 (depends on 1)

2-Halofuryl/thienyl-3-carboxamides of the formula (I) according to claim 1, in which
R represents hydrogen, and
Z represents Z1.

### Claim 8 (depends on 1)

2-Halofuryl/thienyl-3-carboxamides of the formula (I) according to claim 1, in which
R represents hydrogen, and
Z represents Z3.

### Claim 9 (depends on 1)

2-Halofuryl/thienyl-3-carboxamides of the formula (I) according to claim 1, in which
R represents hydrogen, and
Z represents Z4.

### Claim 10 (depends on 1)

2-Halofuryl/thienyl-3-carboxamides of the formula (I) according to claim 1, in which
R represents hydrogen,
R7 represents hydrogen or fluorine, and
Z represents Z3.

### Claim 11 (depends on 10)

2-Halofuryl/thienyl-3-carboxamides of the formula (I) according to claim 10, in which
Z3 represents unsubstituted C2-C20-alkyl.

### Claim 12

N-[2-(1,3-dimethylbutyl)phenyl]-2-iodothiophene-3-carboxamide: