US2010216849A1PendingUtilityA1
Biphenylcarboxamides
Est. expiryDec 13, 2022(expired)· nominal 20-yr term from priority
Inventors:Ralf DunkelHans-Ludwig ElbeHeiko RieckUlrike Wachendorff-NeumannPeter DahmenPeter LöselKarl-Heinz KuckAstrid Mauler-MachnikJörg Nico Greul
C07C 225/22C07D 207/34C07C 251/48C07D 231/16A01N 43/78A01N 43/08C07D 327/06C07D 277/56A61P 33/14A01N 43/40A01N 43/56C07D 213/82A01N 43/10A01N 37/22C07D 231/14C07D 307/68A01N 43/32C07D 333/38
50
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Claims
Abstract
This invention relates to novel biphenylcarboxamides of the formula (I) in which R, Z, X, Y, m, n and A are as defined in the disclosure, to a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and to novel intermediates and their preparation.
Claims
exact text as granted — not AI-modified1 - 14 . (canceled)
15 . A biphenylcarboxamide of formula (I)
in which
R represents hydrogen or C 1 -C 6 -alkyl; or represents C 1 -C 3 -haloalkyl having 1 to 7 fluorine, chlorine, and/or bromine atoms,
Z represents C 3 -C 8 -alkenyl or C 3 -C 8 -alkynyl; represents C 3 -C 8 -haloalkenyl or C 3 -C 8 -haloalkynyl having 1 to 5 fluorine, chlorine, and/or bromine atoms; or represents (C 3 -C 8 -cycloalkyl)(C 1 -C 4 -alkyl),
X and Y independently of one another represent halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, or C 1 -C 8 -alkylthio, or represent C 1 -C 8 -haloalkyl, C 1 -C 8 -haloalkoxy, or C 1 -C 6 -haloalkylthio having 1 to 13 fluorine, chlorine, and/or bromine atoms,
m represents 0, 1, 2, 3, or 4, with the proviso that X represents identical or different radicals when m represents 2, 3, or 4,
n represents 0, 1, 2, 3, or 4, with the proviso that Y represents identical or different radicals when n represents 2, 3, or 4, and
A represents
(ii) a radical of the formula
in which
R 4 and R 5 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 6 represents halogen, cyano or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having 1 to 5 halogen atoms,
or
(iii) a radical of the formula
in which
R 7 and R 8 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 9 represents hydrogen, halogen, or C 1 -C 4 -alkyl,
or
(iv) a radical of the formula
in which R 19 represents hydrogen, halogen, hydroxyl, cyano, or C 1 -C 6 -alkyl; or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, or C 1 -C 4 -halo-alkylthio having 1 to 5 halogen atoms,
or
(v) a radical of the formula
in which
R 11 represents halogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylthio; or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, or C 1 -C 4 -haloalkylthio having 1 to 5 halogen atoms, and
R 12 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, or C 1 -C 4 -alkylsulfonyl; or represents C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having 1 to 5 halogen atoms,
or
(vi) a radical of the formula
in which
R 13 represents C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 14 represents C 1 -C 4 -alkyl,
X 1 represents S, SO, SO 2 , or CH 2 , and
p represents 0, 1, or 2,
or
(vii) a radical of the formula
in which R 15 represents C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(viii) a radical of the formula
in which R 16 represents C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(x) a radical of the formula
in which
R 20 and R 21 independently of one another represent hydrogen, halogen, amino, or C 1 -C 4 -alkyl or represent C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 22 represents hydrogen, halogen, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xi) a radical of the formula
in which
R 23 and R 24 independently of one another represent hydrogen, halogen, amino, nitro, or C 1 -C 4 -alkyl or represent C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 25 represents hydrogen, halogen, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xvi) a radical of the formula
in which R 33 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xvii) a radical of the formula
in which R 34 represents hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 2 -haloalkyl having 1 to 5 halogen atoms.
16 . A biphenylcarboxamide of formula (I) as claimed in claim 15 in which
R represents hydrogen, C 1 -C 4 -alkyl, or C 1 -C 3 -haloalkyl having 1 to 7 fluorine, chlorine, and/or bromine atoms, Z represents C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl; represents C 3 -C 6 -haloalkenyl or C 3 -C 6 -haloalkynyl having 1 to 5 fluorine, chlorine, and/or bromine atoms; or represents (C 3 -C 6 -cycloalkyl)-(C 1 -C 4 -alkyl), X and Y independently of one another represent fluorine, chlorine, bromine, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, or C 1 -C 6 -alkylthio, or represent C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy, or C 1 -C 2 -haloalkylthio having 1 to 5 fluorine, chlorine, and/or bromine atoms, m represents 0, 1, 2, or 3, with the proviso that X represents identical or different radicals when m represents 2 or 3, n represents 0, 1, 2, or 3, with the proviso that Y represents identical or different radicals when m represents 2 or 3, and A represents
(ii) a radical of the formula
in which
R 4 and R 5 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, and
R 6 represents fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, trifluoromethyl, or C 1 -C 2 -haloalkoxy having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(iii) a radical of the formula
in which
R 7 and R 8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, and
R 9 represents hydrogen, fluorine, chlorine, bromine, methyl, or ethyl,
or
(iv) a radical of the formula
in which R 10 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, or C 1 -C 4 -alkyl; or represents C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy, or C 1 -C 2 -haloalkylthio having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(v) a radical of the formula
in which
R 11 represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C 1 -C 4 -alkyl, methoxy, ethoxy, methylthio, or ethylthio; represents C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy having 1 to 5 fluorine, chlorine, and/or bromine atoms; or represents trifluoromethylthio or difluoromethylthio, and
R 12 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, C 1 -C 4 -alkyl, methoxy, ethoxy, methylthio, ethylthio, C 1 -C 2 -alkyl-sulfinyl, or C 1 -C 2 -alkylsulfonyl; or represents C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(vi) a radical of the formula
in which
R 13 represents methyl or ethyl, or represents C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms,
R 14 represents methyl or ethyl,
X 1 represents S, SO, SO 2 , or CH 2 , and
p represents 0, 1, or 2,
or
(vii) a radical of the formula
in which R 15 represents methyl or ethyl, or represents C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(viii) a radical of the formula
in which R 16 represents methyl or ethyl, or represents C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(x) a radical of the formula
in which
R 20 and R 21 independently of one another represent hydrogen, fluorine, chlorine, bromine, amino, methyl, or ethyl, or represent C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, and
R 22 represents hydrogen, fluorine, chlorine, bromine, methyl, or ethyl, or represents C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(xi) a radical of the formula
in which
R 23 and R 24 independently of one another represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, or ethyl, or represent C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, and
R 25 represents hydrogen, fluorine, chlorine, bromine, methyl, or ethyl, or represents C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(xvi) a radical of the formula
in which
R 33 represents methyl, ethyl, or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(xvii) a radical of the formula
in which
R 34 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or trifluoromethyl.
17 . A biphenylcarboxamide of formula (I) as claimed in claim 15 in which
R represents hydrogen, methyl, ethyl, isopropyl, or tert-butyl, Z represents allyl, 2-butenyl, 2-methylallyl, 1-methylallyl, 3-methyl-2-butenyl, propargyl, 2-butynyl, 3-butynyl, 2-methyl-3-butynyl, 3,3-difluoroallyl, 3,3-dichloroallyl, cyclopropylmethyl, cyclopentylmethyl, or cyclohexylmethyl, X and Y independently of one another represent fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, methylthio, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, or difluorochloromethylthio, m represents 0 or 1, n represents 0, 1, or 2, with the proviso that Y represents identical or different radicals when n represents 2, and A represents
(ii) a radical of the formula
in which
R 4 and R 5 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, or trichloromethyl, and
R 6 represents fluorine, chlorine, bromine, cyano, methyl, trifluoro-methyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, or trichloromethoxy,
or
(iii) a radical of the formula
in which
R 7 and R 8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, or trichloromethyl, and
R 9 represents hydrogen, fluorine, chlorine, bromine, methyl, or ethyl,
or
(iv) a radical of the formula
in which R 19 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio, or trichloromethylthio,
or
(v) a radical of the formula
in which
R 11 represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, trifluoro-methoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, difluoromethylthio, or trifluoromethylthio, and
R 12 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, or trichloromethoxy,
or
(vi) a radical of the formula
in which
R 13 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
R 14 represents methyl or ethyl,
X 1 represents S, SO, SO 2 , or CH 2 , and
p represents 0, 1, or 2,
or
(vii) a radical of the formula
in which R 15 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
or
(viii) a radical of the formula
in which R 16 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
or
(x) a radical of the formula
in which
R 20 and R 21 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl, and
R 22 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloro-methyl,
or
(xi) a radical of the formula
in which
R 23 and R 24 independently of one another represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoro-methyl, difluorochloromethyl, or trichloromethyl, and
R 25 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloro-methyl,
or
(xvi) a radical of the formula
in which R 33 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
or
(xvii) a radical of the formula
in which R 34 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or trifluoromethyl.
18 . A biphenylcarboxamide as claimed in claim 15 having formula (I-1)
in which R, Z, X, Y, m, n, and A are as defined for formula (I) in claim 15 .
19 . A process for preparing a biphenylcarboxamide having the formula
in which
R represents hydrogen or C 1 -C 6 -alkyl; or represents C 1 -C 3 -haloalkyl having 1 to 7 fluorine, chlorine, and/or bromine atoms,
Z represents C 3 -C 8 -alkenyl or C 3 -C 8 -alkynyl; represents C 3 -C 8 -haloalkenyl or C 3 -C 8 -haloalkynyl having 1 to 5 fluorine, chlorine, and/or bromine atoms; or represents (C 3 -C 8 -cycloalkyl)(C 1 -C 4 -alkyl),
X and Y independently of one another represent halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, or C 1 -C 8 -alkylthio, or represent C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, or C 1 -C 6 -haloalkylthio having 1 to 13 fluorine, chlorine, and/or bromine atoms,
m represents 0, 1, 2, 3, or 4, with the proviso that X represents identical or different radicals when m represents 2, 3, or 4,
n represents 0, 1, 2, 3, or 4, with the proviso that Y represents identical or different radicals when n represents 2, 3, or 4, and
A represents
(i) a radical of the formula
in which
R 1 represents hydrogen, cyano, halogen, nitro, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, amino-carbonyl, or aminocarbonyl-C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, or C 1 -C 4 -haloalkylthio having 1 to 5 halogen atoms,
R 2 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylthio, and
R 3 represents hydrogen, C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; represents C 1 -C 4 -haloalkyl, halo(C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl), or halo(C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) having 1 to 5 halogen atoms; or represents phenyl,
or
(ii) a radical of the formula
in which
R 4 and R 5 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 6 represents halogen, cyano or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having 1 to 5 halogen atoms,
or
(iii) a radical of the formula
in which
R 7 and R 8 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 9 represents hydrogen, halogen, or C 1 -C 4 -alkyl,
or
(iv) a radical of the formula
in which R 10 represents hydrogen, halogen, hydroxyl, cyano, or C 1 -C 6 -alkyl; or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, or C 1 -C 4 -haloalkylthio having 1 to 5 halogen atoms,
or
(v) a radical of the formula
in which
R 11 represents halogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylthio; or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, or C 1 -C 4 -haloalkylthio having 1 to 5 halogen atoms, and
R 12 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, or C 1 -C 4 -alkyl-sulfonyl; or represents C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having 1 to 5 halogen atoms,
or
(vi) a radical of the formula
in which
R 13 represents C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 14 represents C 1 -C 4 -alkyl,
X 1 represents S, SO, SO 2 , or CH 2 , and
p represents 0, 1, or 2,
or
(vii) a radical of the formula
in which R 15 represents C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(viii) a radical of the formula
in which R 16 represents C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(ix) a radical of the formula
in which
R 17 represents halogen, cyano, C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 18 represents hydrogen, halogen, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 19 represents hydrogen, cyano, C 1 -C 4 -alkyl, 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 -alkysulfonyl, di(C 1 -C 4 -alkyl)-aminosulfonyl, C 1 -C 6 -alkylcarbonyl; or represents optionally substituted phenylsulfonyl or benzoyl,
or
(x) a radical of the formula
in which
R 20 and R 21 independently of one another represent hydrogen, halogen, amino, or C 1 -C 4 -alkyl or represent C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 22 represents hydrogen, halogen, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xi) a radical of the formula
in which
R 23 and R 24 independently of one another represent hydrogen, halogen, amino, nitro, or C 1 -C 4 -alkyl or represent C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 25 represents hydrogen, halogen, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xii) a radical of the formula
in which
R 26 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, cyano, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 27 represents halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xiii) a radical of the formula
in which
R 28 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, cyano, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 29 represents halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xiv) a radical of the formula
in which R 30 represents halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xv) a radical of the formula
in which
R 31 represents hydrogen or C 1 -C 4 -alkyl, and
R 32 represents halogen or C 1 -C 4 -alkyl,
or
(xvi) a radical of the formula
in which R 33 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xvii) a radical of the formula
in which R 34 represents hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 2 -haloalkyl having 1 to 5 halogen atoms,
comprising
(a) reacting a carboxylic acid derivative of formula (II)
in which
A is as defined above, and
G represents halogen, hydroxyl, or C 1 -C 6 -alkoxy,
with an aniline derivative of formula (III)
in which R, Z, X, Y, m, and n are as defined above,
optionally in the presence of a catalyst, optionally in the presence of an acid binder, and optionally in the presence of a diluent,
or
(b) reacting a carboxamide derivative of formula (IV)
in which
A, X, and m are as defined above, and
Hal 1 represents bromine or iodine,
with a boronic acid derivative of formula (V)
in which
R, Z, Y, and n are as defined above, 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) reacting a carboxamide boronic acid derivative of formula (VI)
in which
A, X, and m are as defined above, and
G 1 and G 2 each represent hydrogen or together represent tetramethylethylene,
with a phenyl oxime derivative of formula (VII)
in which
R, Z, Y, and n are as defined above, and
Hal 1 represents bromine or iodine,
in the presence of a catalyst, optionally in the presence of an acid binder, and optionally in the presence of a diluent,
or
(d) reacting a biphenylacyl derivative of formula (VIII)
in which A, R, X, Y, m, and n are as defined above, with a hydroxylamine derivative of formula (IX)
Z—O—NH 2 ×HCl (IX)
in which Z is as defined above,
optionally in the presence of an acid binder and optionally in the presence of a diluent,
or
(e) reacting a hydroxyimino derivative of formula (I-a)
in which A, R, X, Y, m, and n are as defined above,
with a compound of formula (X)
Z-E (X)
in which
Z is as defined above, and
E represents chlorine, bromine, iodine, methanesulfonyl, or p-toluenesulfonyl,
optionally in the presence of an acid binder and optionally in the presence of a diluent,
or
(f) reacting a carboxamide derivative of formula (IV)
in which
A, X, and m are as defined above, and
Hal 1 represents bromine or iodine,
with a phenyl oxime derivative of formula (VII)
in which
R, Z, Y, and n are as defined above, and
Hal 1 represents bromine or iodine,
in the presence of a palladium or platinum 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.
20 . A composition for controlling unwanted microorganisms comprising one or more biphenylcarboxamides of formula (I) as claimed in claim 15 and one or more extenders and/or surfactants.
21 . A method for controlling unwanted microorganisms comprising applying an effective amount of one or more biphenylcarboxamides of formula (I) as claimed in claim 15 to the microorganisms and/or their habitat.
22 . A process for preparing compositions for controlling unwanted microorganisms comprising mixing one or more biphenylcarboxamides of the formula (I) according to claim 15 with one or more extenders and/or surfactants.
23 . An aniline derivative of formula (III)
in which
R represents hydrogen or C 1 -C 6 -alkyl; or represents C 1 -C 3 -haloalkyl having 1 to 7 fluorine, chlorine, and/or bromine atoms,
Z represents C 3 -C 8 -alkenyl or C 3 -C 8 -alkynyl; represents C 3 -C 8 -haloalkenyl or C 3 -C 8 -haloalkynyl having 1 to 5 fluorine, chlorine, and/or bromine atoms; or represents (C 3 -C 8 -cycloalkyl)(C 1 -C 4 -alkyl),
X and Y independently of one another represent halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, or C 1 -C 8 -alkylthio, or represent C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, or C 1 -C 6 -haloalkylthio having 1 to 13 fluorine, chlorine, and/or bromine atoms,
m represents 0, 1, 2, 3, or 4, with the proviso that X represents identical or different radicals when m represents 2, 3, or 4, and
n represents 0, 1, 2, 3, or 4, with the proviso that Y represents identical or different radicals when n represents 2, 3, or 4.
24 . A boronic acid derivative of formula (V)
in which
R represents hydrogen or C 1 -C 6 -alkyl; or represents C 1 -C 3 -haloalkyl having 1 to 7 fluorine, chlorine, and/or bromine atoms,
Z represents C 3 -C 8 -alkenyl or C 3 -C 8 -alkynyl; represents C 3 -C 8 -haloalkenyl or C 3 -C 8 -haloalkynyl having 1 to 5 fluorine, chlorine, and/or bromine atoms; or represents (C 3 -C 8 -cycloalkyl)(C 1 -C 4 -alkyl),
Y represents halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, or C 1 -C 8 -alkylthio, or represent C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, or C 1 -C 6 -haloalkylthio having 1 to 13 fluorine, chlorine, and/or bromine atoms,
n represents 0, 1, 2, 3, or 4, with the proviso that Y represents identical or different radicals when n represents 2, 3, or 4, and
G 1 and G 2 each represent hydrogen or together represent tetramethylethylene.
25 . A carboxamide boronic acid derivative of formula (VI)
in which
G 1 and G 2 each represent hydrogen or together represent tetramethylethylene,
X represents halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, or C 1 -C 8 -alkylthio, or represent C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, or C 1 -C 6 -haloalkylthio having 1 to 13 fluorine, chlorine, and/or bromine atoms,
m represents 0, 1, 2, 3, or 4, with the proviso that X represents identical or different radicals when m represents 2, 3, or 4, and
A represents
(i) a radical of the formula
in which
R 1 represents hydrogen, cyano, halogen, nitro, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, aminocarbonyl, or aminocarbonyl-C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, or C 1 -C 4 -haloalkylthio having 1 to 5 halogen atoms,
R 2 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylthio, and
R 3 represents hydrogen, C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; represents C 1 -C 4 -haloalkyl, halo(C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl), or halo(C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) having 1 to 5 halogen atoms; or represents phenyl,
or
(ii) a radical of the formula
in which
R 4 and R 5 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 6 represents halogen, cyano or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having 1 to 5 halogen atoms,
or
(iii) a radical of the formula
in which
R 7 and R 8 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 9 represents hydrogen, halogen, or C 1 -C 4 -alkyl,
or
(iv) a radical of the formula
in which R 10 represents hydrogen, halogen, hydroxyl, cyano, or C 1 -C 6 -alkyl; or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, or C 1 -C 4 -halo-alkylthio having 1 to 5 halogen atoms,
or
(v) a radical of the formula
in which
R 11 represents halogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylthio; or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, or C 1 -C 4 -haloalkylthio having 1 to 5 halogen atoms, and
R 12 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, or C 1 -C 4 -alkylsulfonyl; or represents C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having 1 to 5 halogen atoms,
or
(vi) a radical of the formula
in which
R 13 represents C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 14 represents C 1 -C 4 -alkyl,
X 1 represents S, SO, SO 2 , or CH 2 , and
p represents 0, 1, or 2,
or
(vii) a radical of the formula
in which R 15 represents C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(viii) a radical of the formula
in which R 16 represents C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(ix) a radical of the formula
in which
R 17 represents halogen, cyano, C 1 -C 4 -alkyl or represents C 1 -C 4 -halo-alkyl having 1 to 5 halogen atoms,
R 18 represents hydrogen, halogen, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 19 represents hydrogen, cyano, C 1 -C 4 -alkyl, 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 -alkysulfonyl, di(C 1 -C 4 -alkyl)aminosulfonyl, C 1 -C 6 -alkyl-carbonyl; or represents optionally substituted phenylsulfonyl or benzoyl,
or
(x) a radical of the formula
in which
R 20 and R 21 independently of one another represent hydrogen, halogen, amino, or C 1 -C 4 -alkyl or represent C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 22 represents hydrogen, halogen, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xi) a radical of the formula
in which
R 23 and R 24 independently of one another represent hydrogen, halogen, amino, nitro, or C 1 -C 4 -alkyl or represent C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 25 represents hydrogen, halogen, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xii) a radical of the formula
in which
R 26 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, cyano, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 27 represents halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xiii) a radical of the formula
in which
R 28 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, cyano, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 29 represents halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xiv) a radical of the formula
in which R 30 represents halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xv) a radical of the formula
in which
R 31 represents hydrogen or C 1 -C 4 -alkyl, and
R 32 represents halogen or C 1 -C 4 -alkyl,
or
(xvi) a radical of the formula
in which R 33 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xvii) a radical of the formula
in which R 34 represents hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 2 -haloalkyl having 1 to 5 halogen atoms.
26 . A biphenylacyl derivative of formula (VIII)
in which
R represents hydrogen or C 1 -C 6 -alkyl; or represents C 1 -C 3 -haloalkyl having 1 to 7 fluorine, chlorine, and/or bromine atoms,
X and Y independently of one another represent halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, or C 1 -C 8 -alkylthio, or represent C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, or C 1 -C 6 -haloalkylthio having 1 to 13 fluorine, chlorine, and/or bromine atoms,
m represents 0, 1, 2, 3, or 4, with the proviso that X represents identical or different radicals when m represents 2, 3, or 4,
n represents 0, 1, 2, 3, or 4, with the proviso that Y represents identical or different radicals when n represents 2, 3, or 4, and
A represents
(i) a radical of the formula
in which
R 1 represents hydrogen, cyano, halogen, nitro, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, aminocarbonyl, or aminocarbonyl-C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, or C 1 -C 4 -haloalkylthio having 1 to 5 halogen atoms,
R 2 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylthio, and
R 3 represents hydrogen, C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; represents C 1 -C 4 -haloalkyl, halo(C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl), or halo(C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl) having 1 to 5 halogen atoms; or represents phenyl,
or
(ii) a radical of the formula
in which
R 4 and R 5 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 6 represents halogen, cyano or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having 1 to 5 halogen atoms,
or
(iii) a radical of the formula
in which
R 7 and R 8 independently of one another represent hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 9 represents hydrogen, halogen, or C 1 -C 4 -alkyl,
or
(iv) a radical of the formula
in which R 10 represents hydrogen, halogen, hydroxyl, cyano, or C 1 -C 6 -alkyl; or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, or C 1 -C 4 -halo-alkylthio having 1 to 5 halogen atoms,
or
(v) a radical of the formula
in which
R 11 represents halogen, hydroxyl, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -alkylthio; or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, or C 1 -C 4 -haloalkylthio having 1 to 5 halogen atoms, and
R 12 represents hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, or C 1 -C 4 -alkylsulfonyl; or represents C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy having 1 to 5 halogen atoms,
or
(vi) a radical of the formula
in which
R 13 represents C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
R 14 represents C 1 -C 4 -alkyl,
X 1 represents S, SO, SO 2 , or CH 2 , and
p represents 0, 1, or 2,
or
(vii) a radical of the formula
in which R 15 represents C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(viii) a radical of the formula
in which R 16 represents C 1 -C 4 -alkyl or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(ix) a radical of the formula
in which
R 17 represents halogen, cyano, C 1 -C 4 -alkyl or represents C 1 -C 4 -halo-alkyl having 1 to 5 halogen atoms,
R 18 represents hydrogen, halogen, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 19 represents hydrogen, cyano, C 1 -C 4 -alkyl, 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 -alkysulfonyl, di(C 1 -C 4 -alkyl)aminosulfonyl, C 1 -C 6 -alkyl-carbonyl; or represents optionally substituted phenylsulfonyl or benzoyl,
or
(x) a radical of the formula
in which
R 20 and R 21 independently of one another represent hydrogen, halogen, amino, or C 1 -C 4 -alkyl or represent C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 22 represents hydrogen, halogen, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xi) a radical of the formula
in which
R 23 and R 24 independently of one another represent hydrogen, halogen, amino, nitro, or C 1 -C 4 -alkyl or represent C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 25 represents hydrogen, halogen, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xii) a radical of the formula
in which
R 26 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, cyano, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 27 represents halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xiii) a radical of the formula
in which
R 28 represents hydrogen, halogen, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, cyano, or C 1 -C 4 -alkyl; or represents C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 29 represents halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xiv) a radical of the formula
in which R 30 represents halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xv) a radical of the formula
in which
R 31 represents hydrogen or C 1 -C 4 -alkyl, and
R 32 represents halogen or C 1 -C 4 -alkyl,
or
(xvi) a radical of the formula
in which R 33 represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(xvii) a radical of the formula
in which R 34 represents hydrogen, halogen, C 1 -C 4 -alkyl, or C 1 -C 2 -haloalkyl having 1 to 5 halogen atoms.
27 . A 2-benzaldehyde aniline derivative of formula (XIV)
in which
R represents hydrogen or C 1 -C 6 -alkyl; or represents C 1 -C 3 -haloalkyl having 1 to 7 fluorine, chlorine, and/or bromine atoms,
X and Y independently of one another represent halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, or C 1 -C 8 -alkylthio, or represent C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, or C 1 -C 6 -haloalkylthio having 1 to 13 fluorine, chlorine, and/or bromine atoms,
m represents 0, 1, 2, 3, or 4, with the proviso that X represents identical or different radicals when m represents 2, 3, or 4, and
n represents 0, 1, 2, 3, or 4, with the proviso that Y represents identical or different radicals when n represents 2, 3, or 4.Cited by (0)
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