ZA200300634B - Pyrazolyl biphenyl carboxamides and the use thereof for controlling undesired microorganisms. - Google Patents
Pyrazolyl biphenyl carboxamides and the use thereof for controlling undesired microorganisms. Download PDFInfo
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- ZA200300634B ZA200300634B ZA200300634A ZA200300634A ZA200300634B ZA 200300634 B ZA200300634 B ZA 200300634B ZA 200300634 A ZA200300634 A ZA 200300634A ZA 200300634 A ZA200300634 A ZA 200300634A ZA 200300634 B ZA200300634 B ZA 200300634B
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- 244000005700 microbiome Species 0.000 title claims description 9
- FAENXWZZEZJZRI-UHFFFAOYSA-N 2-phenyl-n-(1h-pyrazol-5-yl)benzamide Chemical class C=1C=CC=C(C=2C=CC=CC=2)C=1C(=O)NC=1C=CNN=1 FAENXWZZEZJZRI-UHFFFAOYSA-N 0.000 title 1
- -1 cyano, hydroxyl Chemical group 0.000 claims description 37
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 239000011737 fluorine Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 claims description 22
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 21
- 150000003254 radicals Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 239000011230 binding agent Substances 0.000 claims description 18
- 239000003085 diluting agent Substances 0.000 claims description 18
- QBEDVAITPGJZDQ-UHFFFAOYSA-N N1N=C(C=C1)C1=C(C(=CC=C1)C1=CC=CC=C1)C(=O)N Chemical class N1N=C(C=C1)C1=C(C(=CC=C1)C1=CC=CC=C1)C(=O)N QBEDVAITPGJZDQ-UHFFFAOYSA-N 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 16
- 125000001246 bromo group Chemical group Br* 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 claims description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002443 hydroxylamines Chemical class 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 7
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 239000004606 Fillers/Extenders Substances 0.000 claims 2
- BLLGDDLTTAIIQY-UHFFFAOYSA-N anilinoboronic acid Chemical class OB(O)NC1=CC=CC=C1 BLLGDDLTTAIIQY-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- 101001009851 Rattus norvegicus Guanylate cyclase 2G Proteins 0.000 claims 1
- 239000007858 starting material Substances 0.000 description 6
- 150000001448 anilines Chemical class 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- DKPSTXBYINXPMQ-UHFFFAOYSA-N (4-methoxyimino-2-methylcyclohexa-1,5-dien-1-yl)boronic acid Chemical compound CON=C1CC(=C(C=C1)B(O)O)C DKPSTXBYINXPMQ-UHFFFAOYSA-N 0.000 description 1
- CQUUMTZPPFIMML-UHFFFAOYSA-N 2-(4-methoxyimino-2-methylcyclohexa-1,5-dien-1-yl)aniline Chemical compound CON=C1CC(=C(C=C1)C1=C(N)C=CC=C1)C CQUUMTZPPFIMML-UHFFFAOYSA-N 0.000 description 1
- JKSOKTDAASTKIR-UHFFFAOYSA-N 5-fluoro-1,3-dimethylpyrazole-4-carbonyl chloride Chemical compound CC1=NN(C)C(F)=C1C(Cl)=O JKSOKTDAASTKIR-UHFFFAOYSA-N 0.000 description 1
- QJYVDSVBTAZDFC-UHFFFAOYSA-N 6-bromo-N-methoxy-2-methylcyclohexa-2,4-dien-1-imine Chemical compound BrC1C(C(=CC=C1)C)=NOC QJYVDSVBTAZDFC-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- YGRFXPCHZBRUKP-UHFFFAOYSA-N Methoxamine hydrochloride Chemical compound Cl.COC1=CC=C(OC)C(C(O)C(C)N)=C1 YGRFXPCHZBRUKP-UHFFFAOYSA-N 0.000 description 1
- LPLFUPWLRDWMNM-UHFFFAOYSA-N [2-[(5-fluoro-1,3-dimethylpyrazole-4-carbonyl)amino]phenyl]boronic acid Chemical compound CC1=NN(C)C(F)=C1C(=O)NC1=CC=CC=C1B(O)O LPLFUPWLRDWMNM-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001188 haloalkyl group Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960004269 methoxamine hydrochloride Drugs 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- YSPCAFKVLJNIKC-UHFFFAOYSA-N n-(2-bromophenyl)-5-fluoro-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C(F)=C1C(=O)NC1=CC=CC=C1Br YSPCAFKVLJNIKC-UHFFFAOYSA-N 0.000 description 1
- UBUVLOLQZSPUSN-UHFFFAOYSA-N n-[2-(4-acetylphenyl)-4-fluorophenyl]-5-fluoro-1,3-dimethylpyrazole-4-carboxamide Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC(F)=CC=C1NC(=O)C1=C(F)N(C)N=C1C UBUVLOLQZSPUSN-UHFFFAOYSA-N 0.000 description 1
- ZIAROMQBOOKFGR-UHFFFAOYSA-N n-cyclohexyl-5-fluoro-1,3-dimethyl-n-phenylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C(F)=C1C(=O)N(C=1C=CC=CC=1)C1CCCCC1 ZIAROMQBOOKFGR-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C223/00—Compounds containing amino and —CHO groups bound to the same carbon skeleton
- C07C223/06—Compounds containing amino and —CHO groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
PYRAZOLYLBIPHENYLCARBOXAMIDES AND THEIR USE FOR
CONTROLLING UNDESIRABLE MICROORGANISMS
The present invention relates to novel pyrazolylbiphenylcarboxamides. io a plurality of processes for their preparation and to their use for controlling undesirable microorganisms.
It is already known that numerous carboxanilides have fungicidal properties (compare WO 93/11 117, EP-A 0545099, EP-A 0589301, WO 99/09013, DE 198 40 322). Thus, N-(2-cyclohexyl)-1,3-dimethyl-5-fluoropyrazole-4-carboxanilide,
N-{2-phenyl)-1,3-dimethyl-pyrazole-4-carboxanilide and N-[2-(2-fluoro-phenyl)]- 1,3-dimethyl-pyrazole-4-carboxanilide can be employed for controlling fungi. The activity of these substances is good; however, in some cases it is unsatisfactory at low application rates.
This invention, accordingly, provides novel pyrazolylbiphenylcarboxamides of the formula (I) o) Xen
N o NH
N F
CH, Y; CC @,
No _R 2
R in which
R' represents hydrogen, C;-Cg-alkyl, C,-C¢-halogenoalkyl, benzyl or pyridylmethyl,
R’ represents hydrogen or C,-Cg-alkyl,
X represents halogen, nitro, cyano, hydroxyl, carboxyl, C;-Cg-alkyl, C,-C¢- halogenoalkyl having 1 to 5 halogen atoms, C,-Cg-alkoxy, C;-C¢- halogenoalkoxy having 1 to 5 halogen atoms, C;-Cs-alkylthio, C;-Cs- halogenoalkylthio having 1 to 5 halogen atoms, C,-Csg-alkenyloxy. Ca-Cs- alkinyloxy, C;-Cs-cycloalkyl, C,-Cg-alkoxycarbonyl or represents —C(R7)=N-
OR’, m represents integers from 0 to 3, where X represents identical or different radicals if m represents 2 or 3,
Y represents halogen, nitro, cyano, hydroxyl, carboxyl, C;-Cg-alkyl, C;-C¢- halogenoalkyl having 1 to 5 halogen atoms, C,-Cg-alkoxy, C;-Ce- halogenoalkoxy having 1 to 5 halogen atoms, C,-Cg-alkylthio, C;-C¢- halogenoalkylthio having 1 to 5 halogen atoms, C,;-Cg-alkenyloxy, C,-Cs- alkinyloxy, C3-Cg-cycloalkyl, C;-Cg-alkoxycarbonyl or C,-C¢-alkoximino-C;-
Cs-alkyl and n represents integers from O to 4, where Y represents identical or different radicals if n represents 2, 3 or 4.
Furthermore, it has been found that pyrazolylbiphenylcarboxamides of the formula (I) are obtained when a) carboxylic acid derivatives of the formula (II)
0
H,C
G
Y \ (ID)
CH, in which
G represents halogen, hydroxyl or C,-Cs-alkoxy, are reacted with aniline derivatives of the formula (II)
Xm
H,N wt] m 1
No _R
R2 in which
R'.R% X, m, Y and n are each as defined above, if appropriate in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or b) carboxamide derivatives of the formula (IV)
Br
Oo
H.C Xn
N
Wy \ 4
Na av)
CH, in which
X and m are each as defined above, are reacted with boronic acid derivatives of the formula (V) 1 2
G 05g _0OG
Ys; 1 \"
R? in which
R', R?, Y and n are each as defined above and
G' and G? each represent hydrogen or together represent tetramethyl- ethylene, if appropriate in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or : c) carboxamide-boronic acid derivatives of the formula (VI)
O
H,C. Xen
N ty \ 3 B
CH, in which
X and m are each as defined above and
G' and G? each represent hydrogen or together represent tetramethyl- ethylene, are reacted with phenyloxime derivatives of the formula (VII)
Br
Ys VII 1
R2 in which
R, R2Y and n are each as defined above, if appropriate in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or d) biphenylacyl derivatives of the formula (VIII)
0 Xm
N
N NH
N F
CH, Y; (VID) 0
R? in which
RZ, X, m, Y and n are each as defined above and are reacted with alkoxamines of the formula (IX)
R~O-NH, x HCI (IX) in which R'is as defined above, . if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or e) hydroxylamine derivatives of the formula (I-a) 0 Xen
N o WH
N F
CH, y (I-a) 0 No ~ "OH
R> in which
R? X, m, Y and n are each as defined above, are reacted with compounds of the formula (X) 3 _ in which
R} represents C,-Cg-alkyl and
E represenis chlorine, bromine, iodine, methanesulphonyl or p- toluenesulphonyl, or
R’ and E together represent di-C,-Ce-alkyl sulphate, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or f) carboxamide derivatives of the formula (IV)
Br 0
H,C Xm
N
/ \\ H
AN
NF av)
CH,
in which
X and m are each as defined above, are reacted with phenyloxime derivatives of the formula (VII)
Br
Y; : (VID)
R® in which
R', R2, Y and n are each as defined above, in the presence of a palladium or platinum catalyst and in the presence of 4,4.4'4' 5,55" 5'-octamethyl-2,2"-bis-1,3,2-dioxaborolane, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Finally, it has been found that the novel pyrazolylbiphenylcarboxamides of the formula (I) have very good microbicidal properties and can be used for controlling undesirable microorganisms both in crop protection and in the protection of materials.
Surprisingly, the pyrazolylbiphenylcarboxamides of the formula (I) according to the invention have considerably better fungicidal activity than the active prior-art compounds of the most similar constitution and the same direction of action.
The formula (I) provides a general definition of the pyrazolylbiphenylcarboxamides according to the invention. :
R' preferably represents hydrogen, C;-Cy-alkyl, C;-C,-halogenoalkyl having 1 to fluorine, chlorine and/or bromine atoms, benzyl or pyridylmethyl.
R? preferably represents hydrogen or C;-Cj-alkyl. 5
X preferably represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, C-Cg-alkyl, Ci-Cs-halogenoalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C;-Cg-alkoxy, C;-C>-halogenoalkoxy having | to 5 fluorine, chlorine and/or bromine atoms, C,;-C¢-alkylthio, C;-C-- halogenoalkylthio having 1 to 5 fluorine, chlorine and/or bromine atoms, C,-
Ce-alkenyloxy, Cs-Ce-alkinyloxy, C3-C;-cycloalkyl, C;-Cs-alkoxycarbonyl or represents C(R%)=N-OR'. m preferably represents integers from 0 to 3, where X represents identical or different radicals if m represents 2 or 3.
Y preferably represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, C,-Ce-alkyl, C;-C,-halogenoalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C;-C¢-alkoxy, C,-C;-halogenoalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, C;-C¢-alkylthio, C;-C,- halogenoalkylthio having 1 to 5 fluorine, chlorine and/or bromine atoms, C,-
Ce-alkenyloxy, C;-Cs-alkinyloxy, Cs-C;-cycloalkyl, C,-Cs-alkoxycarbonyl or
C;-Cy4-alkoximino-C,-Cy-alkyl. n preferably represents integers from O to 3, where Y represents identical or different radicals if n represents 2 or 3.
R' particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-chloroethyl, benzyl, 2-pyridylmethyl, 3- pyridylmethyl or 4-pyridylmethyl.
R’ particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl or n-butyl.
X particularly preferably represents fluorine, chlorine, bromine, nitro, cyano. hydroxyl, carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl. i- butyl, tert-butyl, trichloromethyl, trifluoromethyl, difluoromethyl, difluoro- chloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy. methylthio, trifluoromethylthio, difluorochloromethylthio, ~~ allyloxy, propargyloxy, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl. methoxycarbonyl, ethoxycarbonyl or represents —C(R*)=N-OR'. m particularly preferably represents integers from 0 to 2, where X represents identical or different radicals if m represents 2.
Y particularly preferably represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i- butyl, tert-butyl, trichloromethyl, trifluoromethyl, difluoromethyl, difluoro- chloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, trifluoromethylthio, difluorochloromethylthio, allyloxy, propargyloxy, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, methoxycarbonyl, ethoxycarbonyl or methoximinomethyl. n particularly preferably represents integers from 0 to 2, where Y represents identical or different radicals if n represents 2.
Preference is also given to compounds of the formula (I-b)
S11 -
O
H,C XX / \ N | ZA
N_ a
I
CH
I (I-b)
R* UN
Osg' in which
R', RZ, X, mm, Y and n are each as defined above.
Particular preference is given to compounds of the formula (I-b) in which R!, RZ, X, m, Y and n have the meanings given above as being preferred or as being particularly preferred.
Preference is furthermore given to compounds of the formula (I-c)
O Xn ey A
JY A R?
N
Sn OR (I-c)
CH, Ys in which :
R', RZ, X, m, Y and n are each as defined above.
Particular preference is given to compounds of the formula (I-c) in which R', R% X, m, Y and n have the meanings given above as being preferred or as being particularly preferred.
Preference is furthermore given to compounds of the formula (I-d) 0]
H.C (>
X
N m o NR
N F
CH
EERE S No _R
Ze (Id)
RC in which
R',R% X,m, Y and n are each as defined above.
Particular preference is given to compounds of the formula (I-d) in which R', R? X, m, Y and n have the meanings given above as being preferred or as being particularly preferred.
Preference or particular preference is given to compounds which carry the substituents mentioned under preferred or particularly preferred.
Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, can in each case be straight-chain or branched as far as this is possible, including in combination with hetero atoms, such as, for example, in alkoxy.
Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution the substituents can be identical or different. A plurality of radicals having the same indices, such as, for example, m radicals X for m>1, can be identical or different.
Halogen-substituted radicals, such as, for example, halogenoalkyl, are mono- or polyhalogenated. In the case of polyhalogenation, the halogen atoms can be identical or different. Here. halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
However, the abovementioned general or preferred radical definitions or illustrations can also be combined with one another as desired, i.e. including combinations between the respective ranges and preferred ranges. The definitions apply to the end products and, correspondingly, to the precursors and intermediates.
The abovementioned definitions can be combined with one another as desired.
Moreover, individual definitions may not apply.
Using 1,3-dimethyl-5-fluoropyrazole-4-carbonyl chloride and 2-(4-methoximino- methyl-phenyl)aniline as starting materials, the course of the process (a) according to the invention can be illustrated by the equation below.
H,C C—ClI H,N H.C, 3% pe
Ne E + base Nay F
N -HCI
CH, CH;
NS
N NS
! ~
CH
: Och,
Using 2’-bromo-1,3-dimethyl-5-fluoropyrazol-4-carboxanilide and (4-methoximino- methyl)-phenylboronic acid as starting materials and a catalyst, the course of the process (b) according to the invention can be illustrated by the equation below.
Br. 0 | N 0
H,C x P HO OH H.C
N
4 \ H . catalyst Rd \ H ~N —_— ~N yo Vr
CH, CH, x
N XX
N
Ow
CH, O-
CH,
Using 2-[(1,3-dimethyl-5-fluoropyrazol-4-yl)carbonylamino]phenyl-boronic acid and 1-bromo-2-methoximinomethyl-benzene as starting materials and a catalyst, the course of the process (c) according to the invention can be illustrated by the equation below. oO 0}
Nae Br H.C
N o N / SN td ~
NL) - Bt N™" CH, NW H <0
N Ho” “OH - NF C NCH,
CH, catalyst CH,
Using 2’-(4-acetyl-phenyl)-4’-fluoro-1,3-dimethyl-5-fluoropyrazole-4-carboxanilide and methoxamine hydrochloride as starting materials, the course of the process (d) according to the invention can be illustrated by the equation below.
F F
O 0]
H,C HC
N N
/ \ H / \ H
N N
SN F H,C—O—NH, N F + ———— x HCI
CH, CH,
HC” ~0 H,C SN lo) : “CH,
Using 2’-(4-hydroximinoethyl)-phenyl-1,3-dimethyl-5-fluoropyrazole-4-carbox- anilide and methyl bromide as starting materials, the course of the process (e) according to the invention can be illustrated by the equation below.
LO LD
H,C H,C *N~ °F 4g + HC—Br ——= "°F
CH, CH,
H,C ~N H,C SN
OH Och,
Using 2’-bromo-1,3-dimethyl-5-fluoropyrazole-4-carboxanilide and 1-bromo-4- methoximinomethyl-benzene as starting materials and a catalyst and 4,4,4°,4°5,5,5",5 -octamethyl-2,2"-bis-1,3,2-dioxaborolane, the course of the process (f) according to the invention can be illustrated by the equation below.
Br 0
Br H,C ©
Q N
H,C pO catalyst RU \ H —_—— \ HN + 0» “NTF
N x as pw
N F NS °° CH,
N
CH, oo ~
CH, N
Oo “CH,
Illustration of the processes and intermediates
The formula (II) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out the process (a) according to the invention. In this formula, G preferably represents chlorine, bromine, hydroxyl, methoxy or ethoxy, particularly preferably chlorine, hydroxyl or methoxy.
The carboxylic acid derivatives of the formula (II) are known or can be prepared by known processes (cf. WO 93/11 117, EP-A 0545099, EP-A0589301 and
EP-A 0 589 313).
The formula (II) provides a general definition of the aniline derivatives required as reaction components for carrying out the process (a) according to the invention. In this formula, R', R?, X, m, Y and n each preferably have those meanings which have already been mentioned in connection with the description of the substances of the formula (I) according te the invention as being preferred or being particularly preferred for these radicals or indices.
The aniline derivatives of the formula (I) are novel. Some of them can be prepared by known methods (cf. EP-A 0 545 099 and EP-A 0 589 301).
The aniline derivatives of the formula (II) are furthermore obtained by 2) reacting 2-halogenoaniline derivatives of the general formula (XI)
X m ; Hal (XI)
NH
2 in which
X and m are each as defined above and
Hal represents halogen, with boronic acid derivatives of the formula (V)
Claims (21)
- Patent ClaimsI. Pyrazolylbiphenylcarboxamides of the formula (I) o Xen H,C / N No \ "i N CH, vy. C . 1 NR 2 R in which R! represents hydrogen, C,-Cs-alkyl, C,-Ce¢-halogenoalkyl, benzyl or pyndylmethyl, R® represents hydrogen or C;-Cg-alkyl, X represents halogen, nitro, cyano, hydroxyl, carboxyl, C;-Cg-alkyl, C,- Ce-halogenoalkyl having 1 to 5 halogen atoms, C;-Cg-alkoxy, C,-Cs- halogenoalkoxy having 1 to 5 halogen atoms, C;-Cg-alkylthio, C;-Cs- halogenoalkylthio having I to 5 halogen atoms, C,-Cg-alkenyloxy, C,- Cg-alkinyloxy, C;-Cg-cycloalkyl, C;-Cg-alkoxycarbonyl or represents ~C(R*»=N-OR/, m represents integers from 0 to 3, where X represents identical or different radicals if m represents 2 or 3, Y represents halogen, nitro, cyano, hydroxyl, carboxyl, C;-Cs-alkyl, C;- Ce-halogenoalkyl having 1 to 5 halogen atoms, C;-Cg-alkoxy, C;-Cs- halogenoalkoxy having 1 to 5 halogen atoms, C;-Cg-alkylthio, C,-Cs- ]halogenoalkylthio having 1 to 5 halogen atoms, C,-Cs-alkenyloxy, Cs- Cs-alkinyloxy, Cs-Cg-cycloalkyl, C;-Cs-alkoxycarbonyl or C,-Cs- alkoximino-C,-Ce-alkyl and S n represents integers from O to 4, where Y represents identical or different radicals if n represents 2, 3 or 4.
- 2. Pyrazolylbiphenylcarboxamides of the formula (I) according to Claim | in which R! represents hydrogen, C,-Cs-alkyl, C,-C,-halogenoalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, benzyl or pyridylmethyl, R2 represents hydrogen or C,-Cy-alkyl, X represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, C,-Cg-alkyl, C;-C,-halogenoalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C;-Cs-alkoxy, C,-C,-halogenoalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, C;-Cg- alkylthio, C;-C;-halogenoalkylthio having 1 to 5 fluorine, chlorine and/or bromine atoms, C,-Cs-alkenyloxy, C,-Cg-alkinyloxy, Cs-C;- cycloalkyl, C;-C4-alkoxycarbonyl or represents -C(R*)=N-OR!, m represents integers from 0 to 3, where X represents identical or different radicals if m represents 2 or 3, Y represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, C;-Ce-alkyl, C;-C,-halogenoalkyl having | to 5 fluorine, chlorine and/or bromine atoms, C,-Cs-alkoxy, C;-C,-halogenoalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, C;-Cs- alkylthio, C;-C;-halogenoalkylthio having 1 to 5 fluorine, chlorine and/or bromine atoms, C,-Cg-alkenyloxy, C,-Cs-alkinyloxy, Ci-Cs- cycloalkyl, C;-Cs-alkoxycarbonyl or C;-Cy-alkoximino-C,-Cj-alkyl, n represents integers from 0 to 3, where Y represents identical or different radicals if n represents 2 or 3.
- 3. Pyrazolylbiphenylcarboxamides of the formula (I) according to Claim 1 in which : R' represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-chloroethyl, benzyl, 2-pyridylmethyl, 3-pyridyl- methyl or 4-pyridylmethyl, R’ represents hydrogen, methyl, ethyl, n-propyl, i-propyl or n-butyl, X represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl, tert-butyl, trichloromethyl, trifluoromethyl, difluoromethyl, difluoro- chloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methyithio, trifluoromethylthio, difluorochloromethylthio, ailyloxy, propargyloxy, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, methoxycarbonyl, ethoxycarbonyl or represents -C(R%)=N-OR!, m represents integers from O to 2, where X represents identical or different radicals if m represents 2, Y represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl, tert-butyl, trichloromethyl, trifluoromethyl, difluoromethyl, difluoro- chloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, trifluoromethylthio, difluorochloromethylthio, allyloxy, !propargyloxy, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, methoxycarbonyl, ethoxycarbonyl or methoximinomethyl, n represents integers from O to 2, where Y represents identical or different radicals if n represents 2.
- 4. Process for preparing pyrazolylbiphenylcarboxamides of the formula (I) according to Claim 1, characterized in that a) carboxylic acid derivatives of the formula (II) Oo H,C G AN N F (I CH, in which G represents halogen, hydroxyl or C,-C¢-alkoxy, are reacted with aniline derivatives of the formula (II) § Xn H,N Y; C] (II) PIN R2 in whichR', R% X, m, Y and n are each as defined in Claim 1, if appropriate in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or b) carboxamide derivatives of the formula (IV)Br 0) H,C Xm N / \\ H nN" °F av) CH, in which X and m are each as defined in Claim 1,are reacted with boronic acid derivatives of the formula (V) 1 2 G 05g 0G Ys 1 \% RZ in whichR!, RZ, Y and n are each as defined in Claim 1 andG' and G? each represent hydrogen or together represent tetramethyl- ethylene, if appropriate in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or c) carboxamide-boronic acid derivatives of the formula (VI) o : HC Xn N : vy \ : B ~ VI) F 7 NA A2 ( N c'o” TOG CH, in which X and m are each as defined in Claim | and G' and G? each represent hydrogen or together represent tetramethyl- ethylene, : are reacted with phenyloxime derivatives of the formula (VII) Br Y 1 vil En, R vib R2 in whichR!, R? Y and n are each as defined in Claim 1, if appropriate in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or d) biphenylacyl derivatives of the formula (VII) 0 Xn we, A N NN H ~ F N (VII) CH, Ys 0 R? in which R?, X, m, Y and n are each as defined in Claim 1, are reacted with alkoxamines of the formula (IX)in which R' is as defined in Claim 1, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent,{or e) hydroxylamine derivatives of the formula (I-a) 0) Xen N Yi WA oN EF CH - 3; A y (I-a) Z “OH R® in which R2, X, m, Y and n are each as defined in Claim 1, are reacted with compounds of the formula (X) 3 in whichR? represents C-Cgq-alkyl and E represents chlorine, bromine, iodine, methanesulphonyl or p- toluenesulphonyl,or R}and E together represent di-C;-Cq-alkyl sulphate,if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or f) carboxamide derivatives of the formula (IV) Br 0 : H,C Xen N 7\ H No NF Iv) : CH, in which X and m are each as defined in Claim 1, are reacted with phenyloxime derivatives of the formula (VII) Br Yi 1 VII NR (VID RZ in which R, R?, Y and n are each as defined in Claim 1, in the presence of a palladium or platinum catalyst and in the presence of 44.4'4'5,5,5',5-octamethyl-2,2'-bis-1,3,2-dioxaborolane, if t appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
- 5. Pyrazolylbiphenylcarboxamides of the formula (I-b) 0 N Ne VR N F CH I-b sv: C] (I-b) R*T IN ON 1 R in which R',R% X, m, Y and n are each as defined in Claim 1.
- 6. Pyrazolylbiphenylcarboxamides of the formula (I-c)0H.C ( N 4 \ N R? NN F i XO CH, C7 N"TOR (Io) Ya; in which R',R? X, m, Y and n are each as defined in Claim 1.
- 7. Pyrazolylbiphenylcarboxamides of the formula (I-d)0 H,C N Xm o WH N F CH, vy $ n 1 Ns o-R (Id) rR? in which R!, R?, X, m, Y and n are each as defined in Claim 1.
- 8. Aniline derivatives of the formula (II) CJ H,N (I) Y i x NS AR R2 in which R',R?% X, m, Y and n are each as defined in Claim 1.
- 9. Process for preparing aniline derivatives of the formula (Il) according to Claim 8, characterized in that g) 2-halogenoaniline derivatives of the general formula (XI) ¢X m Hal (XI) NH, in which X and m are each as defined in Claim 1 andHal represents halogen, are reacted with boronic acid derivatives of the formula (V) 1 2 G OSs 0G Ya 1 \'% NF v) 2 R in which R', R?, Y and n are each as defined in Claim 1 and G' and G? each represent hydrogen or together represent tetramethyl- ethylene, if appropriate in the presence of an acid binder, and if appropriate in the presence of an inert organic diluent, and if appropriate in the presence of a catalyst,or h) anilineboronic acids of the formula (XII)X m NH, 8 (XID) G'07 0G? in which X and m are each as defined in Claim 1 and G' and G? each represent hydrogen or together represent tetramethyl- ethylene, are reacted with phenyloxime derivatives of the formula (VII) Br Ya 1 vi R2 in which R!, R?, Y and n are each as defined in Claim 1, if appropriate in the presence of an acid binder, and if appropriate in the presence of an inert organic diluent, and if appropriate in the presence of a catalyst.
- 10. Boronic acid derivatives of the formula (V) {G'o___0G? B Ys; 1 \" R? in which R', R? Y and n are each as defined in Claim 1 and G' and G* each represent hydrogen or together represent tetramethylethylene.
- 11. Process for preparing boronic acid derivatives of the formula (V) according to Claim 10, characterized in that 1) phenylboronic acids of the formula (XIII) R2 G'O \ A ° G20 (X11) Ya in which R?, Y and n are each as defined in Claim | and G' and G? each represent hydrogen or together represent tetramethyl- ethylene, are reacted with alkoxamines of the formula (IX) R™—0—NH, x HCI (IX)in which R'is as defined in Claim 1, if appropriate in the presence of an acid binder, and if appropriate in the presence of an inert organic diluent, and if appropriate in the presence of a catalyst.
- 12. Carboxamide-boronic acid derivatives of the formula (VI) O H,G xX, N Rd \\ H 5 (VI) oN F G'07 “og? CH, in which X and m are each as defined in Claim 1 and G' and G* each represent hydrogen or together represent tetramethylethylene.
- 13. Process for preparing carboxamide-boronic acid derivatives of the formula (VI) according to Claim 12, characterized in that ) carboxylic acid derivatives of the formula (II) 0 H,GC G 7 \ No EN . (ID Chi in which G is as defined in Claim 1, h) are reacted with anilineboronic acids of the formula (XII) X m NH, B (XII) G'0” ~0G’ in which X and m are each as defined in Claim 1 and G' and G® each represent hydrogen or together represent tetramethylethylene, if appropriate in the presence of an acid binder, and if appropriate in the presence of an inert organic diluent, and if appropriate in the presence of a catalyst.
- 14. Biphenylacyl derivatives of the formula (VIII) o Xen H,C / N Ne \ ! CH, Tn (VII) 0) R?in which RZ, X, m, Y and n are each as defined in Claim 1.
- 15. Process for preparing biphenylacyl derivatives of the formula (VII) according to Claim 14, characterized in that k) carboxylic acid derivatives of the formula (IT) Oo H,C G /\ AN (ID CH, in which G is as defined in Claim 1, are reacted with 2-benzaldehyde-aniline derivatives of the formula (XIV) (r H,N CJ (XIV) Ya R? O in which R2, X, m, Y and h are each as defined in Claim 1,if appropriate in the presence of an acid binder, and if appropriate in the presence of an inert organic diluent.
- 16. 2-Benzaldehyde-aniline derivatives of the formula (XIV) (h- HN (J) 0 (XIV) Ya R? in which R?, X, mm, Y and n are each as defined in Claim 1.
- 17. Process for preparing 2-benzaldehyde-aniline derivatives of the formula (XIV) according to Claim 16, characterized in that 1) aniline derivatives of the formula (XI) X m Hal (XI) NH, in which X and m are each as defined in Claim 1 and Hal represents halogen,are reacted with phenylboronic acid derivatives of the formula (XIII) R? G'Q ° 2 A (XT) GO Ya in which R?, Y and n are each as defined in Claim 1 and G' and G? each represent hydrogen or together represent tetramethyl- ethylene, if appropriate in the presence of an acid binder, and if appropriate in the presence of an inert organic diluent.
- 18. Compositions for controlling undesirable microorganisms, characterized in that they comprise at least one pyrazolylbiphenylcarboxamide of the formula (I) according to Claim 1, in addition to extenders and/or surfactants.
- 19. Use of pyrazolylbiphenylcarboxamides of the formula (I) according to Claim 1 for controlling undesirable microorganisms.
- 20. Method for controlling undesirable microorganisms, characterized in that pyrazolylbiphenylcarboxamides of the formula (I) according to Claim 1 are applied to the microorganisms and/or their habitat.
- 21. Process for preparing compositions for controlling undesirable microorganisms, characterized in that pyrazolylbiphenylcarboxamides of the formula (I) according to Claim 1 are mixed with extenders and/or surfactants.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10035860 | 2000-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200300634B true ZA200300634B (en) | 2004-02-10 |
Family
ID=7649940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200300634A ZA200300634B (en) | 2000-07-24 | 2003-01-23 | Pyrazolyl biphenyl carboxamides and the use thereof for controlling undesired microorganisms. |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR100850236B1 (en) |
| DE (1) | DE10122097A1 (en) |
| ZA (1) | ZA200300634B (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116063226B (en) * | 2023-03-15 | 2023-06-02 | 云南省农业科学院茶叶研究所 | Ether compound containing monoterpene phenol structure |
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| DE19840322A1 (en) * | 1998-09-04 | 2000-03-09 | Bayer Ag | Pyrazole carboxanilides |
-
2001
- 2001-05-07 DE DE10122097A patent/DE10122097A1/en not_active Withdrawn
- 2001-07-11 KR KR1020037000222A patent/KR100850236B1/en not_active IP Right Cessation
-
2003
- 2003-01-23 ZA ZA200300634A patent/ZA200300634B/en unknown
Also Published As
| Publication number | Publication date |
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| DE10122097A1 (en) | 2002-02-07 |
| KR100850236B1 (en) | 2008-08-04 |
| KR20030031556A (en) | 2003-04-21 |
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