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  • 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
  • C07D213/60—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 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
  • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
  • C07D213/81—Amides; Imides
  • C07D213/82—Amides; Imides in position 3
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  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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  • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
  • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
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  • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
  • C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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  • 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
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  • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
  • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
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  • 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
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  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
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  • 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
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  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
  • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
  • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
  • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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  • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
  • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
  • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
  • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

• the present invention relates to new biphenylcarboxamides, several ner processes for their preparation and their use for controlling unwanted microorganisms.
• R 11 represents halogen, hydroxyl, cyano, CC 4 -alkyl, C 4 alkoxy, CC 4 alkyl thio, C ⁇ -C haloalkyl, C ⁇ -C4-haloalkoxy, C ⁇ -C 4 -haloalkylthio each with 1 to 5 halogen atoms
• R 12 represents hydrogen, halogen, cyano, C r C 4 alkyl, C 1 -C 4 alkoxy, CC 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl or C ⁇ -C 4 halo-alkyl, C ⁇ -C4-haloalkoxy having in each case 1 to 5 halogen atoms, or a represents a radical of the formula
• R 18 represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 5 -haloalkyl having 1 to 5 halogen atoms,
• R 28 is hydrogen, halogen, amino, C ⁇ -C 4 alkylamino, di- (C ⁇ -C 4 - alkyl) amino, cyano, C 4 alkyl or C ⁇ -C 4 -halogenoalkyl having 1 to 5 halogen atoms
• R 29 fiir halogen, C ⁇ -C4 alkyl or C ⁇ -C is 4 -halogenoalkyl having 1 to 5 halogen atoms, or a represents a radical of the formula
• R 33 is C 4 alkyl or C ⁇ -4 -halogenoalkyl having 1 to 5 halogen atoms for C ⁇ -C, or A for a residue of the formula
• R, Z, Y and n have the meanings given above and
• G and G each represent hydrogen or together represent tetramethylethylene, 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 (VT)
• the biphenylcarboxamides of the formula (I) according to the invention have a substantially better fungicidal activity than the structurally most similar, known active ingredients of the same action.
• R 7 and R 8 independently of one another are hydrogen, fluorine, chlorine, bromine, methyl, ethyl or -CC 2 haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms and
• R 10 for hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C 1 -C 4 alkyl, C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy, C 1 -C 2 haloalkylthio, each with 1 to 5 fluorine -, Chlorine and / or bromine atoms.
• R 16 represents methyl, ethyl or CC 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
• A also preferably represents a radical of the formula
• A also preferably represents a radical of the formula
• R 25 stands for hydrogen, fluorine, chlorine, bromine, methyl, ethyl or for C r C 2 - haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
• A also preferably represents a radical of the formula
• R 33 represents methyl, ethyl or C r C 2 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
• Residues is when n is 2.
• A also particularly preferably represents a radical of the formula
• R 4 and R 5 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl and
• R 10 for hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec.-butyl, tert-butyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, Trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio.
• R 22 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
• R and R independently of one another represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and
• R 25 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. also particularly preferably represents a radical of the formula
• A also particularly preferably represents a radical of the formula
• R 28 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl and
• R 29 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
• A also particularly preferably represents a radical of the formula
• R 30 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
• R 31 represents hydrogen, methyl or ethyl
• m very particularly preferably represents 0 or 1.
• n very particularly preferably represents 0 or 1.
• a very particularly preferably represents a radical of the formula embedded image in which
• A also very particularly preferably represents a radical of the formula
• A also very particularly preferably represents a radical of the formula
• R 9 represents methyl
• R .11 represents fluorine, chlorine, bromine, methyl or trifluoromethyl
• A also very particularly preferably represents a radical of the formula
• A also very particularly preferably represents a radical of the formula embedded image in which
• A also very particularly preferably represents a radical of the formula
• R 28 represents fluorine, chlorine, amino or methyl
• R 31 represents methyl
• R 33 represents methyl, trifluoromethyl or difluoromethyl.
• Z particularly particularly preferably represents allyl, 2-methyl-allyl, 1-methyl-allyl, 3-methyl-2-butenyl, propargyl, 2-butynyl, 3,3-difluoroallyl, cyclopropylmethyl.
• X is particularly preferably fluorine
• m is particularly preferably 0 or 1.
• n is particularly preferably 0.
• a particularly particularly preferably represents a radical of the formula
• R 1 represents methyl, monofluoromethyl, difluoromethyl or trifluoromethyl
• A also particularly particularly preferably represents a radical of the formula embedded image in which
• R, 12 represents hydrogen
• A also particularly particularly preferably represents a radical of the formula
• R represents hydrogen or methyl and R 19 represents methyl.
• A also particularly particularly preferably represents a radical of the formula embedded image in which
• R 90 and R 1 each represent hydrogen and
• R 22 represents methyl
• R 97 represents methyl, trifluoromethyl or difluoromethyl.
• A also particularly particularly preferably represents a radical of the formula
• Preferred, particularly preferred, very particularly preferred or in particular very particularly preferred are compounds which carry the substituents mentioned under preferred, particularly preferred, very particularly preferred or in particular very particularly preferred.
• Optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
• residues with the same indices such as m residues X for m> 1, can be the same or different.
• Residues substituted by halogen are halogenated once or more than once.
• the halogen atoms can be the same or different.
• Halogen stands for fluorine, chlorine, bromine and iodine, in particular for fluorine, chlorine and bromine.
• the general definitions or explanations of residues or explanations listed above or in preferred areas can, however, also be combined with one another as desired, that is to say between the respective areas and preferred areas. They apply accordingly to the end products as well as to the preliminary and intermediate products. In addition, individual definitions can also be omitted.
• aniline derivatives of the formula (in) are new. Some of them can be produced by known methods (cf. EP-A 0 545 099 and EP-A 0 589301). Aniline derivatives of the formula (HI) are also obtained by
• the formula (XH) provides a general definition of the aniline boronic acids required as reaction components when carrying out processes (h) and (j) (see below).
• X and m preferably have those meanings which are preferred in connection with the description of the substances of the formula (I) according to the invention, particularly preferably, very particularly preferably or in particular
• the boronic acid derivatives of the formula (V) are new and can be prepared by i) phenylboronic acids of the formula (XIII)
• Formula (VI) provides a general definition of the carboxamide-boronic acid derivatives required as reaction components when carrying out process (c) according to the invention.
• A, X and m preferably represent those meanings which, in connection with the description of the substances of the formula (T) according to the invention, are preferred, particularly preferred, very particularly preferred or in particular entirely for these radicals or these indices were particularly preferred.
• G 1 and G 2 are preferably each hydrogen or together tetramethylethylene.
• Formula (VIII) provides a general definition of the biphenylacyl derivatives required as starting materials when carrying out process (d) according to the invention.
• A, R, X, Y, m and n stand for those meanings which, in connection with the description of the substances of the formula (I) according to the invention, are preferred, particularly preferred, very particularly preferred for these radicals or these indices or were particularly particularly preferred.
• Formula (IX) provides a general definition of the hydroxylamine derivatives required as reaction components when carrying out process (d) and process (i) according to the invention.
• Z preferably has those meanings which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention, particularly preferably, very particularly preferably or in particular very particularly preferably for this radical.
• the hydrochlorides specified in the description are preferably used.
• the free hydroxylamine derivatives can also be used in the process according to the invention.
• Hydroxylamine derivatives of the formula (IX) are commercially available.
• hydroxyimino derivatives required as starting materials when carrying out process (e) according to the invention are generally defined by the formula (Ia), in this formula A, R, X, Y, m and n preferably represent those meanings which are already related with the description of the substances of the formula (I) according to the invention for these radicals or these indices as preferred, particularly preferred, very particularly preferred or in particular very particularly preferred.
• hydroxyimino derivatives of the formula (I-a) according to the invention can be prepared by one of the processes (a), (b), (c), (d) or (f) described above.
• Formula (X) provides a general definition of the compounds required as reaction components when carrying out process (e) according to the invention.
• Z preferably represents those meanings which have already been mentioned as preferred, particularly preferred, very particularly preferred or in particular very particularly preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
• E preferably represents chlorine, bromine, iodine, methanesulfonyl or p-toluenesulfonyl.
• Compounds of formula (X) are commercially available.
• Suitable diluents for carrying out processes (a), (b), (c), (d), (e) and (f) are all customary inert, organic solvents.
• Halogenated aliphatic, ahcyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin can preferably be used; Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ni
• reaction temperatures can be varied over a wide range in carrying out processes (a), (b), (c), (d), (e) and (f). In general, temperatures between 0 ° C and 140 ° C, preferably between 10 ° C and 120 ° C.
• the procedure is generally in each case under atmospheric pressure. However, it is also possible to work under increased or reduced pressure.
• 1 mole of carboxamide-boronic acid derivative of the formula (VI) is generally 1 mole or an excess of phenyloxime derivative of the formula (VD) and 1 to 10 moles of acid binder and 0.5 to 5 mole percent of a catalyst.
• the reaction components in other ratios.
• the processing takes place according to usual methods. In general, the procedure is such that water is added to the reaction mixture, the precipitate is separated off and dried. The remaining residue can, if appropriate, be freed of any impurities which may still be present, using customary methods, such as chromatography or recrystallization.
• Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
• Thysanura e.g. Lepisma saccharina.
• Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
• Linognathus spp. Trichodectes spp., Damalinia spp ..
• Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp ..
• Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp ..
• Arachnida class e.g. Sco ⁇ io maurus, Latrodectus mactans, Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommodes spp., Lps.
• Chorioptes spp. Chorioptes spp., Sarcoptes spp., Tarsonernus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp ..
• Plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globqdera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp-, Trichodorus spp., Bursaphelenchus spp ..
• the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
• Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
• Pseudomonas species such as, for example, Pseudomonas syringae pv. Laclirymans;
• Erwinia species such as, for example, Erwinia amylovora;
• Pythium species such as, for example, Pythium ultimum
• Phytophthora species such as, for example, Phytophthora infestans
• Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
• Plasmopara species such as, for example, Plasmopara viticola
• Bremia species such as, for example, Bremia lactucae
• Peronospora species such as, for example, Peronospora pisi or P. brassicae;
• Erysiphe species such as, for example, Erysiphe graminis
• Venturia species such as, for example, Venturia inaequalis
• Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
• Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
• Uromyces species such as, for example, Uromyces appendiculatus
• Puccinia species such as, for example, Puccinia recondita
• Sclerotinia species such as, for example, Sclerotinia sclerotiorum
• Tilletia species such as, for example, Tilletia caries
• Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
• Pellicularia species such as, for example, Pellicularia sasakii;
• Pyricularia species such as, for example, Pyricularia oryzae
• Fusarium species such as, for example, Fusarium culmorum
• Botrytis species such as, for example, Botrytis cinerea
• Septoria species such as, for example, Septoria nodorum
• Cercospora species such as, for example, Cercospora canescens
• Alternaria species such as, for example, Alternaria brassicae;
• Pseudocercosporella species such as, for example, Pseudocercosporella he ⁇ otrichoides.
• the active compounds according to the invention also have a strong strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
• Plant-strengthening (resistance-inducing) substances are to be understood in the present context as substances which are able to stimulate the defense system of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesired microorganisms.
• Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
• the substances according to the invention can thus be used to protect plants against attack by the pests mentioned within a certain period of time after the treatment.
• the period of time within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days, after the plants have been treated with the active compounds.
• the fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
• the active compounds according to the invention can be used with particularly good success to combat diseases in wine, fruit and vegetable cultivation, such as, for example, against Venturia, Botrytis, Sclerotinia, Rhizoctonia, Uncinula, Sphaerotheca, Podosphaera, Altemaria and Colletotrichum species. Rice diseases such as Pyricularia and Pellicularia species are also successfully combated.
• the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
• the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.
• plants and parts of plants can be treated.
• Plants are understood here to mean all plants and plant populations, such as desired and undesirable wild plants or cultivated plants (including naturally occurring cultivated plants).
• Cult plant plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
• Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
• the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
• technical materials are understood to mean non-living materials that have been prepared for use in technology.
• technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms .
• parts of production systems for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms.
• technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood.
• Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
• the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
• Microorganisms of the following genera may be mentioned, for example:
• Chaetomium like Chaetomium globosum
• Coniophora such as Coniophora puetana
• Lentinus such as Lentinus tigrinus, Penicillium, such as Penicillium glaucum, Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonasyloc, such as Pseudomonas, such as Pseudomonas, such as Pseudomonas, such as Pseudomonas, such as Posaomonoc,
• the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV - Cold and warm mist formulations.
• formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
• extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• organic solvents can, for example, also be used as auxiliary solvents.
• aromatics such as xylene, toluene or alkylnaphthalenes
• chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
• aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
• alcohols such as butanol or glycol and their ethers and esters
• ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
• strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
• carboxymethylcellulose and natural and synthetic powders granules or latexf '-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins, and synthetic phospholipids in the Formuliemngen adhesive.
• Other additives can be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
• the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
• the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antifungal effects, in particular against dermatophytes and shoot fungi, mold and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillichophytonyumumatus, fumigatus such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
• the list of these fungi in no way represents a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.
• the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients using the ultra-low-volume process or to prepare the active ingredient or the like Inject active ingredient into the soil yourself. The seeds of the plants can also be treated.
• the agents used to protect industrial materials generally contain the active ingredients in an amount of 1 to 95%, preferably 10 to 75%.
• the application concentrations of the active compounds according to the invention depend on the type and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected.
• the optimal amount can be determined by test series.
• the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.
• the effectiveness and the range of activity of the active ingredients to be used according to the invention in the protection of materials, or of the agents, concentrates or very general formulations that can be produced therefrom, can be increased if further antimicrobially active compounds, fungicides, bactericides, herbicides, insecticides or other active ingredients to enlarge the spectrum of action or Achieving special effects such as added protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.
• the active compounds according to the invention can also be used in their commercially available formulation formulations and in the formulations prepared from these formulations Use forms in a mixture with synergists are available.
• Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.
• the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in mixtures with inhibitors which reduce degradation of the active compound after use in the environment of the plant, on the surface of parts of plants or in plant tissues ,
• the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
• the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
• the active compound When used against hygiene and harmful pests, the active compound is distinguished by an outstanding residual action on wood and clay and by a good stability to alkali on limed substrates.
• all plants and their parts can be treated.
• wild plant species or plant species and their parts obtained by conventional biological breeding methods such as crossing or protoplast fusion, are treated.
• transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
• the term “parts” or “parts of plants” or “parts of plants” was explained above.
• Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
• Plant varieties are plants with new properties ("traits") that can be obtained through conventional breeding, have been grown by mutagenesis or by recombinant DNA techniques. These can be varieties, breeds, bio and genotypes.
• the treatment according to the invention can also cause superadditive (“synergistic") effects.
• superadditive for example, reduced application rates and / or widening of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance , easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and or higher nutritional value of the harvested products, higher storability and / or workability of the harvested products that go beyond the effects that are actually to be expected.
• the preferred transgenic (genetically preserved) plants or plant cultivars to be treated according to the invention include all plants which, through the genetic modification, received genetic material which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better Plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or Machinability of the Harvest Products Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or V iren as well as an increased tolerance of the plants against certain herbicidal active substances.
• microbial pests such as against insects, mites, phytopathogenic fungi, bacteria and / or V iren as well as an increased tolerance of the plants against certain herbicidal active substances.
• transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton, tobacco and rapeseed are highlighted.
• the properties (“traits”) which are particularly emphasized are the plants' increased defense against insects, arachnids, nematodes and snails due to toxins arising in the plants, in particular those which are caused by the genetic material Bacillus thuringiensis (e.g.
• Bt plants The properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
• SAR systemic acquired resistance
• the traits are also particularly emphasized as the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
• herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
• PAT phosphinotricin
• herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties which are marketed under the trade names Roundup Ready ® (tolerance to glyphosates, e.g. maize, cotton, soybeans), Liberty Link ® (tolerance to phosphinotricin, e.g. rape), DVD- ® (tolerance against imidazolinones) and STS ® (tolerance to sulfonylureas such as corn).
• Herbicide-resistant plants (bred conventionally for herbicide tolerance) plants also sold under the name Clearfield ® varieties (eg maize) are mentioned. Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
• plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
• the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
• the mixture is cooled to room temperature and extracted twice with 50 ml of diethyl ether each time.
• the organic phases are washed with water, dried over sodium sulfate and concentrated under reduced pressure.
• the residue is purified by column chromatography on silica gel ( ⁇ exane methyl tert-butyl ether 3: 1).
• the calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms), the LogP values of which are known (determination of the LogP values on the basis of the retention times by linear frit polishing between two successive alkanones).
• the lambda max values were determined using the UN spectra from 200 nm to 400 nm in the
• dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
• the plants are then placed in the greenhouse at approximately 21.degree. C. and a relative atmospheric humidity of approximately 90%.
• Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
• Botrytis test (bean) / protective
• dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
• Emulsifier 1 part by weight of alkyl aryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
• Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
• the plants are then placed in a greenhouse at a temperature of approximately 20 ° C. and a relative atmospheric humidity of 80% in order to promote the development of rust pustules.
• Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
• a specified amount of active ingredient preparation of the desired concentration is pipetted onto a standardized amount of synthetic feed. After the methanol has evaporated, approx. 200-300 eggs of the cockroach (Plutella xylostella) are added to the feed.

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