Biphenylcarboxamides for controlling micro-organisms
View Patent ↗Novel biphenylcarboxamides of the formula (I) There is further provided a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and also novel intermediates and their preparation.
1. A biphenylcarboxamide of formula (I)
in which
R 1 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 8 -alkylthio)carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl)carbonyl, (C 3 -C 6 -alkenyloxy)carbonyl, (C 3 -C 6 -alkynyloxy)-carbonyl, (C 3 -C 8 -cycloalkyl)carbonyl; (C 1 -C 6 -haloalkyl)carbonyl, (C 1 -C 6 -haloalkoxy)carbonyl, (C 1 -C 6 -haloalkylthio)carbonyl, (halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl)carbonyl, (C 3 -C 6 -haloalkenyloxy)carbonyl, (C 3 -C 6 -haloalkynyloxy)carbonyl, (C 3 -C 8 -halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; or —CH 2 —C≡C—R 1-A , —CH 2 —CH═CH—R 1-A , —CH═C═CH—R 1-A , —C(═O)C(═O)R 2 , —CONR 3 R 4 or —CH 2 NR 5 R 6 , R 1-A represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, (C 1 -C 4 -alkoxy)carbonyl, (C 3 -C 6 -alkenyloxy)carbonyl, (C 3 -C 6 -alkynyloxy)carbonyl or cyano,
R 2 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 3 and R 4 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 3 and R 4 furthermore together with the nitrogen atom to which they are attached form a saturated heterocycle which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and C 1 -C 4 -alkyl and which has 5 to 8 ring atoms, where the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulphur and NR 7 ,
R 5 and R 6 independently of one another each 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 5 and R 6 furthermore together with the nitrogen atom to which they are attached form a saturated heterocycle which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and C 1 -C 4 -alkyl and which has 5 to 8 ring atoms, where the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulphur and NR 7 ,
R 7 represents hydrogen or C 1 -C 6 -alkyl,
R 8 represents hydrogen or fluorine,
R 9 represents —SO m R 11 , —SO 2 NR 12 R 13 , —C(═X)R 14 , —NR 12 R 13 , —CH 2 —NR 12 R 13 ,
R 10 represents fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl,
R 11 represents C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl having 1 to 13 halogen atoms,
m represents 1 or 2,
R 12 represents hydrogen, C 1 -C 4 -alkyl or —C(═X)R 14 ,
R 13 represents hydrogen, C 1 -C 4 -alkyl or —C(═X)R 14 ,
R 12 and R 13 furthermore together with the nitrogen atom to which they are attached form a saturated heterocycle which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and C 1 -C 4 -alkyl and which has 5 to 8 ring atoms, where the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulphur and NR 7 ,
X represents O (oxygen) or S (sulphur),
R 14 represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or —NR 16 R 17 ,
R 15 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 or C 1 -C 6 -haloalkyl, where the three radicals R 15 may each be identical or different,
R 16 hydrogen or C 1 -C 4 -alkyl,
R 17 hydrogen or C 1 -C 4 -alkyl,
R 16 and R 17 furthermore together with the nitrogen atom to which they are attached form a saturated heterocycle which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen and C 1 -C 4 -alkyl and which has 5 to 8 ring atoms, where the heterocycle may contain 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulphur and NR 7 ,
A represents one of the radicals A1 to A19 below
R 18 represents hydrogen, cyano, halogen, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy or C 1 -C 4 -haloalkylthio having in each case 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-C 1 -C 4 -alkyl,
R 19 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio,
R 20 represents hydroxy-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cyclo-alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl having in each case 1 to 5 halogen atoms, or phenyl,
R 21 and R 22 independently of one another represent halogen or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 23 represents halogen, cyano, or C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having in each case 1 to 5 halogen atoms,
R 24 and R 25 independently of one another represent halogen or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 26 represents halogen or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 27 represents hydrogen, hydroxyl, cyano, C 1 -C 4 -haloalkoxy or C 1 -C 4 -haloalkylthio having in each case 1 to 5 halogen atoms,
R 28 represents halogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkylthio or C 1 -C 4 -haloalkoxy having in each case 1 to 5 halogen atoms,
R 29 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy having in each case 1 to 5 halogen atoms,
C 1 -C 4 -alkylsulphinyl or C 1 -C 4 -alkylsulphonyl,
R 30 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 31 represents C 1 -C 4 -alkyl,
Q 1 represents S (sulphur), SO, SO 2 or CH 2 ,
p represents 0, 1 or 2, where R 22 represents identical or different radicals if p represents 2,
R 32 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 33 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 34 and R 35 independently of one another represent hydrogen, halogen, amino, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 36 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 37 and R 38 independently of one another represent hydrogen, halogen, amino, nitro, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 39 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 40 represents halogen, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, cyano, C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 41 represents halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 42 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 43 represents halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 44 represents halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 45 represents hydrogen or C 1 -C 4 -alkyl,
R 46 represents halogen or C 1 -C 4 -alkyl,
R 47 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 48 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 50 represents C 1 -C 4 -alkyl,
R 51 represents hydrogen, cyano, C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylsulphonyl, di(C 1 -C 4 -alkyl)aminosulphonyl, C 1 -C 6 -alkylcarbonyl or in each case optionally substituted phenylsulphonyl or benzoyl,
R 52 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 53 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 54 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms.
2. A process for preparing biphenylcarboxamide according to claim 1 , comprising reacting
(a) a carbonyl halide of formula (II)
in which
X 1 represents halogen or hydroxyl,
with an amine of the formula (III)
if appropriate in the presence of a coupling agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent,
or
(b) reacting a biphenylcarboxamide of formula (I-a)
with a halide of formula (IV)
R 1-B -Hal (IV)
in which
R 1-B 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, halogen-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 8 -alkylthio)carbonyl, (C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl)carbonyl, (C 3 -C 6 -alkenyloxy)carbonyl, (C 3 -C 6 -alkynyloxy)carbonyl, (C 3 -C 8 -cycloalkyl)carbonyl; (C 1 -C 6 -haloalkyl)-carbonyl, (C 1 -C 6 -haloalkoxy)carbonyl, (C 1 -C 6 -haloalkylthio)carbonyl, (halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl)carbonyl, (C 3 -C 6 -haloalkenyloxy)carbonyl, (C 3 -C 6 -haloalkynyloxy)carbonyl, (C 3 -C 8 -halocycloalkyl)carbonyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; or —CH 2 —C≡C—R 1-A , —CH 2 —CH═CH—R 1-A , —CH═C═CH—R 1-A , —C(═O)C(═O)R 2 , —CONR 3 R 4 or —CH 2 NR 5 R 6 ,
Hal represents chlorine, bromine or iodine
in the presence of a base and in the presence of a diluent.
3. A composition for controlling an unwanted microorganism, comprising at least one biphenylcarboxamide according to claim 1 and an extender and/or surfactant.
4. A biphenylcarboxamide according to claim 1 for controlling an unwanted microorganism.
5. A method for controlling an unwanted microorganism, comprising applying a biphenylcarboxamide according to claim 1 to a microorganism and/or a habitat thereof.
6. A process for preparing a composition for controlling an unwanted microorganism, comprising mixing a biphenylcarboxamide according to claim 1 with an extender and/or a surfactant.
7. A biphenylcarboxamide according to claim 1 for treating a seed.
8. A biphenylcarboxamide according to claim 1 for treating a transgenic plant.
9. A biphenylcarboxamide according to claim 1 for treating a seed of a transgenic plant.
10. An Amine of formulae (III-1), (III-2) and (III-3)