Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/0803—Compounds with Si-C or Si-Si linkages
  • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages

Definitions

• the present invention relates to novel silylated carboxamides, to a plurality of processes for their preparation and to their use for controlling unwanted microorganisms.
• R is hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl
• L represents a direct bond or represents optionally substituted straight-chain or branched alkylene (alkanediyl), alkenylene (alkenediyl) or alkynylene (alkynediyl),
• R 1 and R 2 independently of one another are hydrogen, C 8 alkyl, CC 8 -alkoxy, C alkoxy - C 4 alkyl, Ci- alkylthio-Ci-Gralkyl or C ß are -haloalkyl
• R 3 is hydrogen, Ci-Cg-alkyl, -Cg-alkoxy, -CC 4 -alkoxy-C C 4 -alkyl, CC 4 -alkylthio-C Gi-alkyl, C 2 -C 8 -alkenyl, C 2 C 8 alkynyl, CC 6 -haloalkyl, CC 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -cycloalkyl, or represents in each case optionally substituted phenyl or phenylalkyl
• R 4 represents hydrogen, CC 8 - alkyl, d-Cg-alkylsulphiny
• (AI) is in which R n is hydrogen, halogen, hydroxy, cyano, CC 6 alkyl, C r C 4 haloalkyl, C 4 - haloalkoxy or C r C 4 -haloalkylthio having in each case 1 to 5 halogen atoms, or A is the radical of the formula (A2)
• a for the rest of the formula (A3) (A3) in which R 13 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, or A is the radical of the formula (A4)
• (A4) stands in which R 13 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, or A is the radical of the formula (A5) (A5), in which R is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 5 halogen atoms, or A is the radical of the formula (A6)
• R 15 is hydrogen, halogen, CrGrAlkyl or Ci-Gj-haloalkyl having 1 to 5 halogen atoms, or A is the radical of the formula (A7)
• R 16 is halogen, hydroxy, CrGrAlkyl, CC 4 -alkoxy, CC 4 alkylthio, CC 4 - haloalkyl, C ⁇ -C4-haloalkylthio or C ⁇ -C is 4 -haloalkoxy having 1 to 5 halogen atoms, or
• A is the radical of formula (A8) R 17 (A8) in which N ⁇ S R 17 is CrGrAlkyl, or A for the rest of the formula (A9)
• A represents the radical of the formula (Al 1) (Al 1) in which in which X is O (oxygen) or S (sulfur), R 18 is iodine or methyl.
• the compounds of the invention may optionally be used as mixtures of various possible isomeric forms, in particular of stereoisomers, such as. B. E and Z, threo and erythro, and optical isomers, but optionally also of tautomers. Both the E and the Z isomers, as well as the threo and erythro, and the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms claimed.
• silylated carboxamides of the formula (I) are obtained by reacting a) carboxylic acid derivatives of the formula (H) O. ., In which X 1 is halogen or hydroxy and A has the meanings given above, with A in of the formula (HI) in which R, L, R 1 , R 2 , R 3 and R 4 have the abovementioned meanings, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or b ) silylated carboxamides of the formula (1-1)
• R, L, R 1 , R 2 , R 3 and A have the meanings given above, with halides of the formula (VET) R x (vm) in which X 2 is chlorine, bromine or iodine, R 4a is CC 8 alkyl, CC 6 alkylsulfmyl, CrC 6 alkylsulfonyl, CrC 4 alkoxyCrC 4 alkyl, C 3 -C 8 cycloalkyl; CC 6 haloalkyl, C ⁇ -C haloalkylthio, CC -Halo- genalkylsulfinyl -C 4 -haloalkylsulfonyl, halo-Ci-C4-alkoxy-C ⁇ -C4-alkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and bromine atoms; Formyl, formyl-CrC 3 -
• silylated carboxamides according to the invention are generally defined by the formula (I).
• Preferred radical definitions of the above and below formulas are given below. These definitions apply equally to the end products of formula (I) as well as to all intermediates.
• R is preferably hydrogen.
• R is furthermore preferably fluorine, with fluorine being particularly preferably in the 4-, 5- or 6-position, very particularly preferably in the 4- or 6-position, in particular in the 4-position of the anilide radical [cf. above formula (I)].
• R is furthermore preferably chlorine, with chlorine being particularly preferably in the 5-position of the anilide radical [cf. above formula (1)].
• R is furthermore preferably methyl, where methyl is particularly preferably in the 3-position of the anilide radical [cf. above formula (I)].
• R is furthermore preferably trifluoromethyl, trifluoromethyl being particularly preferably in the 4- or 5-position of the anilide radical [cf. above formula (1)].
• L preferably represents a direct bond or represents optionally halogen-substituted straight-chain or branched C ⁇ -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene.
• R 1 and R 2 are each independently of the other preferably C 1 -C 6 -alkyl, C -C 6 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 3 -alkyl or C 1 -C 4 -alkylthioalkyl.
• R 1 and R 2 independently of one another particularly preferably represent methyl, ethyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthio methyl, methylthioethyl or ethylthioethyl.
• R 1 and R 2 independently of one another very particularly preferably represent methyl, methoxy, methoxymethyl or methylthiomethyl.
• R 1 and R 2 are particularly preferably each methyl.
• R 3 is preferably C, -C 6 alkyl, CC 6 alkoxy, -C 3 alkoxy, C-C 3 alkyl, C r C 3 alkylthio C ⁇ -C 3 alkyl, C 3 -C 6 cycloalkyl , Phenyl or benzyl.
• R 3 is particularly preferably methyl, ethyl, n- or iso-propyl, n-, sec-, iso- or tert-butyl, methoxy, ethoxy, n- or iso-propoxy, n-, sec-, iso- or tert-butoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, cyclopropyl, phenyl or benzyl.
• R 3 is very particularly preferably methyl, ethyl, n- or isopropyl, iso- or tert-butyl, methoxy, isopropoxy, isobutyl or tert-butoxy, methoxymethyl, methylthiomethyl or phenyl.
• R 3 is particularly preferably methyl, ethyl, n- or iso-propyl, iso- or tert-butyl, methoxy, iso-propoxy, iso- or tert-butoxy.
• R 3 is methyl
• R 4 preferably represents hydrogen, CC 6 alkyl, -C 4 alkylsulfinyl, C ⁇ -C 4 alkylsulfonyl, C alkoxy-Cr alkyl, C 3 -C 6 cycloalkyl; CC 4 -haloalkyl, C 1 -C 4 -haloalkylthio, - C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, halogeno-C 1 -C -alkoxy-C 1 -alkyl, C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or or bromine atoms; Formyl, formyl-C 3 -alkyl, (C 1 -C 3 -alkyl) carbonyl-C 1 -C 3 -alkyl, (CC 3 -alkoxy) carbonyl-C 1
• R 4 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, Trifluoromethyl, trichloromethyl, trifluoroethy
• R 4 is particularly preferably hydrogen.
• R 5 is preferably hydrogen, CrC 6 alkyl, CrC alkoxy, CC 3 alkoxy-CrC 3 alkyl, C 3 - C 6 cycloalkyl; -C 4 haloalkyl, C r C haloalkoxy, halogen-C r C 3 -alkoxy-C ⁇ -C 3 - alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and or bromine atoms.
• R s is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl, methoxy, ethoxy, n- or iso-propoxy, tert-butoxy, methoxymethyl, cyclopropyl; Trifluoromethyl, trifluoromethoxy.
• R 6 and R 7 independently of one another preferably are hydrogen, C 6 alkyl, CC 3 alkoxy-Cr C 3 alkyl, C 3 -C 6 cycloalkyl; C 1 -C 4 -haloalkyl, halogeno-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
• R 6 and R 7 together with the nitrogen atom to which they are attached furthermore preferably form a saturated heterocycle having 5 or 6 ring atoms which is optionally monosubstituted to monosubstituted, identically or differently, by halogen or --C 4 -alkyl, where the hetero-J cyclus may contain 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 10 .
• R 6 and R 7 independently of one another are particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.
• R 6 and R 7 together with the nitrogen atom to which they are attached moreover preferably form a saturated heterocycle from the series morpholine, thiomorpholine or piperazine, optionally monosubstituted to trisubstituted, identically or differently by fluorine, chlorine, bromine or methyl the piperazine may be substituted on the second nitrogen atom by R 10 .
• R 8 and R 9 independently of one another preferably represent hydrogen, -C ⁇ -alkyl, C 3 -C 6 -cycloalkyl; C 1 -C 4 -haloalkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
• R 8 and R 9 furthermore together with the nitrogen atom to which they are bonded preferably form a saturated heterocycle having 5 or 6 ring atoms which is optionally monosubstituted or polysubstituted, identically or differently by halogen or -alkyl, where the heterocycle has 1 or 2 further, may contain non-adjacent heteroatoms from the series oxygen, sulfur or NR 10 .
• R 8 and R 9 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.
• R 8 and R 9 also form, together with the nitrogen atom to which they are bonded, particularly preferably a saturated heterocycle from the series Moholin, thiomethylholin or piperazine which is optionally monosubstituted to disubstituted, identically or differently by fluorine, chlorine, bromine or methyl. wherein the piperazine may be substituted on the second nitrogen atom by R 10 .
• R 10 is preferably hydrogen or C 1 -C 4 -alkyl.
• R 10 is particularly preferably hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl.
• A preferably represents one of the abovementioned radicals AI, A2, A5 or A7.
• A is furthermore preferably A6, A10 or Al1.
• A is particularly preferably the radical AI.
• A is more preferably the radical A2.
• A is moreover preferably the radical A5.
• A is moreover preferably the radical A6.
• A is more preferably the radical A7.
• A is more preferably the radical AI 0.
• A is more preferably the radical A 11.
• R ⁇ is preferably hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, -CC 4 -alkyl, - C 2 -haloalkyl, CC 2 -haloalkoxy or C 1 -C 2 -haloalkylthio each having 1 to 5 fluorine, chlorine and / or bromine atoms.
• R ⁇ particularly preferably 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.
• R 11 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl.
• R ⁇ particularly preferably represents chlorine, bromine, iodine, methyl, difluoromethyl or trifluoromethyl.
• R 12 is preferably iodine.
• R 12 is also preferably chlorine.
• R 12 is also preferably dichloromethyl.
• R 13 is preferably methyl, ethyl or C 1-5 haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
• R 13 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
• R 13 very particularly preferably represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
• R 14 is preferably methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and bromine or bromine.
• R 14 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
• R 14 is very particularly preferably methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
• R 14 is particularly preferably methyl or trifluoromethyl.
• R 15 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 -C 2 -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.
• R 15 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
• R 16 is preferably fluorine, chlorine, bromine, iodine, hydroxy, CC 4 alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, CC 2 -haloalkyl or CC 2 -haloalkoxy each having 1 to 5 fluorine, chlorine and / or bromine atoms.
• R 16 particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl.
• R 16 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
• R 17 is preferably methyl, ethyl, n-propyl or iso-propyl.
• R 17 is particularly preferably methyl or ethyl.
• X is preferably O (oxygen).
• X is also preferably S (sulfur).
• R 18 is preferably iodine.
• R 18 is also preferably methyl.
• R, L, R 1 , R 2 , R 3 and A have the meanings given above.
• R, L, R "1, r R> 2, ⁇ R3, ⁇ R> 4 a and A have the meanings given above.
• R 4a is preferably C r C 6 alkyl, CC 4 alkylsulfinyl, CRQ alkylsulfonyl, C ⁇ -C3 alkoxy-C C 3 alkyl, C 3 -C 6 cycloalkyl; -C 4 haloalkyl, CrGrHalogenalkylthio, -GrHalogen- alkylsulf ⁇ nyl, -C 4 -haloalkylsulfonyl, halo-C C 3 alkoxy-CrC 3 alkyl, C 3 -C 8 -Halo- gencycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-Cr, C 3 -alkyl, (CC 3 -alkyl) carbonyl-CrC 3 -alkyl, (CC 3 -alkoxy) carbonyl-CrC 3 -alkyl; Hal
• R 4a is particularly preferably methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfmyl, n-, iso- , sec- or tert-butylsulfmyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopenyl, cyclohexyl, trifluoromethyl, trichloromethyl, Trifluoroethyl, di
• R, R 1 , R 2 , R 3 , R 4 and A have the meanings given above.
• Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
• heteroatoms e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
• Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
• Halogen substituted radicals e.g. Haloalkyl
• Halogen substituted radicals are halogenated singly or multiply.
• the halogen atoms may be the same or different.
• Halogen stands for fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
• the carboxylic acid derivatives required as starting materials for carrying out the process (a) according to the invention are generally defined by the formula (H).
• A preferably, more preferably or most preferably has those meanings that already in connection with the description of the compounds of the formula (1) according to the invention have been given as preferred, particularly preferred or very particularly preferred for these radicals.
• X 1 is preferably chlorine, bromine or hydroxyl.
• Carboxylic acid derivatives of the formula (D) are known and / or can be obtained by known methods (cf., WO 93/11117, EP-A 0 545 099, EP-A 0 589 301, EP-A 0 589 313 and DE- A 103 25 439.0).
• R, L, R 1 , R 2 , R 3 and R 4 have preferably, more preferably or very particularly preferably those meanings which have already been described in connection with the description of the compounds of the formula (I) as preferred, particularly preferred or very particularly preferred for these radicals.
• the amines of the formula (DI) are known and / or can be obtained in a known manner (cf., WO 03/080628 and the preparation examples).
• Amines of the formula (DI) in which R 4 is not hydrogen can be obtained, for example, by reacting amines of the formula (Tfl-a)
• the silylated carboxamides required as starting materials for carrying out the process (b) according to the invention are generally defined by the formula (1-1).
• R, L, R 1 , R 2 , R 3 , R 4 and A have preferably, more preferably or very particularly preferably those meanings which have already been described in connection with the description of the compounds of the formula (I) as preferred, particularly preferred or very particularly preferred for these radicals.
• the compounds of the formula (1-1) are compounds according to the invention and can be prepared by the process (a).
• Suitable diluents for carrying out process (a) according to the invention are all inert organic solvents. These include, preferably, aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ni
• Suitable diluents for carrying out the process (b) according to the invention are all inert organic solvents. These include, preferably, aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;
• the process (a) according to the invention is carried out in the presence of a suitable acid acceptor.
• a suitable acid acceptor all customary inorganic or organic bases are suitable.
• These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, lithium diisopropylamide, sodium methoxide, sodium ethylate, potassium tert-butoxide, sodium acetate, Potassium acetate, calcium acetate, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and tertiary amines such as trimemylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine , N-methyl
• the process (b) according to the invention is carried out in the presence of a suitable base.
• a suitable base preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, lithium diisopropylamide, sodium methoxide, sodium ethylate, potassium tert-butylate, sodium acetate, potassium acetate, Calcium acetate, ammonium acetate, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium carbonate, potassium carbonate, potassium hydrogencarbonate, sodium hydrogencarbonate or cesium carbonate; and tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpho
• the process (a) according to the invention is carried out in the presence of a suitable condensing agent.
• a suitable condensing agent As such, all commonly used for such Amid istsreak- tions condensing agent come into question. Examples which may be mentioned are acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; Anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropylhexyl isobutyrate, isobutyl chloroformate or methanesulphonyl chloride; Carbodiimides, such as N, N'-dicyclohexylcarbodiimide (DCC) or other conventional condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-e
• the process (a) according to the invention is carried out in the presence of a catalyst.
• a catalyst examples which may be mentioned are 4-dimemylaminopyridine, 1-hydroxybenzotriazole or dimethylformamide.
• the reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, one works at temperatures of 0 ° C to 150 ° C, preferably at temperatures of 0 ° C to 120 ° C, more preferably at temperatures of l0 ° C to 80 ° C.
• reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, one works at temperatures of 0 ° C to 150 ° C, preferably at temperatures of 20 ° C to 110 ° C.
• the substances according to the invention have a strong microbicidal activity and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
• Fungicides can be used for the control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
• Bactericides can be used in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
• Xanthomonas species such as Xanthomonas campestris pv. Oryzae
• Pseudomonas species such as Pseudomonas syringae pv. Lachrymans
• Erwinia species such as Erwinia amylovora
• Pythium species such as Pythium ultimum
• Phytophthora species such as Phytophthora infestans
• Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
• Plasmopara species such as Plasmopara viticola
• Bremia species such as Bre ia lactucae
• Peronospora species such as Peronosporapisi or P. brassicae;
• Erysiphe species such as Erysiphe graminis
• Sphaerotheca species such as Sphaerotheca fuliginea
• Podosphaera species such as Podosphaera leucotricha
• Venturia species such as Venturia inaequalis
• Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
• Cochliobolus species such as Cochliobolus sativus
• Uromyces species such as Uromyces appendiculatus
• Puccinia species such as Puccinia recondita
• Sclerotinia species such as Sclerotinia sclerotiorum
• Tilletia species such as Tilletia caries
• Ustilago species such as Ustilago nuda or Ustilago avenae;
• Pellicularia species such as, for example, Pellicularia sasakii;
• Pyricularia species such as Pyricularia oryzae
• Fusarium species such as Fusarium culmorum
• Botrytis species such as Botrytis cinerea
• Septoria species such as Septoria nodorum
• Leptosphaeria species such as Leptosphaeria nodorum
• Cercospora species such as Cercospora canescens
• Altemaria species such as Alternaria brassicae
• Pseudocercosporella species such as Pseudocercosporella herpotrichoides
• Rhizoctonia species such as Rhizoctonia solani.
• the active compounds according to the invention also have a strong tonic effect in plants. They are therefore suitable for mobilizing plant-own defenses against attack by unwanted microorganisms.
• plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of plants in such a way that the treated plants exhibit extensive resistance to these microorganisms with subsequent inoculation with undesired microorganisms.
• Undesirable microorganisms in the present case are phytopathogenic fungi, bacteria and viruses.
• the substances according to the invention can therefore be used to protect plants within a certain period of time after the treatment against the infestation by the said pathogens.
• the period of time within which protection is afforded generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.
• the good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of aboveground plant parts, of plant and seed, and the soil.
• the active compounds according to the invention can be used with particularly good success for controlling cereal diseases, such as, for example, against Puccinia species and diseases in the cultivation of wine, fruit and vegetables, for example against Botrytis, Venturia or Alternaria species.
• the active compounds according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
• the active compounds according to the invention may optionally 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 other active ingredients.
• plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
• Crop 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 plant varieties which can or can not be protected by plant variety rights.
• Under plant parts everyone should Above-ground and underground parts and organs of the plants, such as shoot, leaf, flower and root are understood, with examples of leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes are listed.
• the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
• the treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, spreading, spreading and in propagation material, in particular in seeds, further by single or multi-layer wrapping.
• the substances according to the invention can be used to protect industrial materials against infestation and destruction by undesired microorganisms.
• Technical materials as used herein mean non-living materials that have been prepared for use in the art.
• technical materials to be protected from microbial alteration or destruction by the active compounds of the invention may be adhesives, glues, paper and board, textiles, leather, wood, paints and plastics, coolants and other materials that may be infested or degraded by microorganisms .
• materials to be protected are also parts of production plants, such as cooling water circuits, called, which can be affected by the proliferation of microorganisms.
• technical materials which may be mentioned are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.
• microorganisms that can cause degradation or a change in the technical materials, for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned.
• the active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
• microorganisms of the following genera are: Alternaria, such as Alternaria tenuis, Aspergillus, such as Aspergillus niger,
• Chaetomium such as 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 Aureohasidium pullulans, Sclerophoma such as Sclerophomapityophila, Trichoderma such as Trichoderma viride, Escherichia such as Escherichia coli, Pseudomonas such as Pseudomonas aeruginosa, Staphylococcus, such as Staphylococcus aureus.
• Coniophora such as Coniophora puetana
• Lentinus such as Lentinus tigrinus
• Penicillium such as Penicillium glaucum
• Polyporus such as Polyporus versicolor
• the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, ultrafine encapsulations in polymeric substances and in seed coating compositions, as well as ULV Cold and warm mist formulations.
• customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, ultrafine encapsulations in polymeric substances and in seed coating compositions, as well as ULV Cold and warm mist formulations.
• formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
• extenders ie liquid solvents, liquefied gases under pressure and / or solid carriers
• surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
• organic solvents as auxiliary solvents.
• Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg 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.
• aromatics such as xylene, toluene or alkylnaphthalenes
• chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
• aliphatic hydrocarbons such
• liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
• Suitable solid carriers are: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates.
• solid carriers for granules are: for example, broken and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
• Emulsifying and / or foam-forming agents are suitable: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates.
• Suitable dispersants are: for example lignin-sulphite liquors and methylcellulose.
• adhesives such as carboxymethylcellulose, natural and synthetic powdery, gromige or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids.
• Other additives may be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan 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.
• inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan 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.
• the formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
• the active compounds according to the invention can also be used in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, so as to obtain e.g. to broaden the spectrum of action or to prevent development of resistance.
• synergistic effects i. E. the effectiveness of the mixture is greater than the effectiveness of the individual components.
• Fungicides are suitable as mixed partners: Fungicides:
• 2-phenylphenol 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; aldimorph; amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; Benodanil;
• benomyl Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; bilanafos; binapacryl; Biphenyl; bitertanol; Blasticidin-S; bromuconazole; Bupirimate; Buthiobate; Burylamin; Calcium polysulfide; capsimycin; captafol; captan; carbendazim; carboxin; Ca ⁇ ropamid; carvones; chinomethionat;
• cyflufenamid cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; Dichlorofluanide; dichlone; dichlorophen; diclocymet; Diclomezine; dicloran; diethofencarb; Difenoconazole;
• Bactericides bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
• Insecticides / acaricides / nematicides Abamectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole, acrinathrin, AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb, aldoxycarb, allethrin, allethrin lR isomers, alpha Cype ⁇ nethrin (alphamethrin), amidoflurnet, aminocarb, amitraz, avermectin, AZ-60541, azadirachtin, azamethiphos, azinphos-methyl, azinphos-ethyl, azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG- 2348, Bacillus thuring
• the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad antimycotic Wirl mg spectrum, especially against dermatophytes and yeasts, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floecosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
• Candida species such as Candida albicans, Candida glabrata
• Epidermophyton floecosum Aspergillus species such as Aspergillus niger and Aspergillus fumigatus
• Trichophyton species such as Trichophyton mentagrophytes
• Microsporon species such as Microsporon canis and audouinii.
• the list of these fungi is by no means
• 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 Powder, dusts and granules are applied.
• the application is carried out in a conventional manner, for example by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc.
• the active ingredients can be applied by the ultra-low-volume method or the active ingredient preparation or the active ingredient itself in the Inject soil. It can also be the seed of the plants to be treated.
• the application rates can be varied within a relatively wide range, depending on the mode of administration.
• the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 ) g / ha.
• the application rates of active ingredient are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
• the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
• plants and their parts can be treated.
• wild species or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
• plant varieties and their parts are treated.
• transgenic plants and plant cultivars obtained by genetic engineering if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
• the term “parts” or “parts of plants” or “plant parts” has been explained above.
• Plant varieties are understood to be plants having new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques, which may be varieties, breeds, biotypes and genotypes.
• the treatment according to the invention may also give rise to superadditive ("synergistic") effects, for example reduced application rates and / or extensions of the activity spectrum and / or a Enhancement of the effect of the substances and agents that can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or against Water or soil salt content, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher harvest value of the harvested products, higher shelf life and or machinability of the harvested products possible, which go beyond the actual expected effects.
• superadditive for example reduced application rates and / or extensions of the activity spectrum and / or a Enhancement of the effect of the substances and agents that can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or against Water or soil salt content, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher harvest value of the harvested products, higher shelf life and or
• the preferred plants or plant cultivars to be treated according to the invention include all plants which have obtained genetic material by the genetic engineering modification 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 dryness or to bottoms, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher harvest value of the harvested products, higher shelf life and / or workability of the product Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances.
• microbial pests such as insects, mites, phytopathogenic fungi, bacteria and / or viruses
• transgenic plants include the important crops such as cereals (wheat, rice), corn, soybean, potato, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybean, potato , Cotton, tobacco and oilseed rape.
• Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a) , CrylAfb), CryIA (c), CryDA, CryDIA, CryDIB2, Cry9c Cry2Ab, Cry3Bb and CryW and their combinations) in the plants (hereinafter "Bt plants”). Traits also highlight 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
• herbicidal active substances for example Imidazolmonen, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
• the genes conferring the desired properties can also be present in combinations with one another in the transgenic plants.
• “Bt plants” are maize varieties, cotton varieties, soybean varieties and potato varieties sold under the trade names YTJBLD GARD® (eg maize , Cotton, soybean), KnockOut® (eg corn), StarLink® (eg corn), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato).
• herbicide tolerant plants are maize varieties, cotton varieties and Soya varieties known under the trade names Roundup Ready® (tolerance to glyphosate eg maize, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance to imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
• Herbicide-resistant (conventionally grown on herbicide tolerance) plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned. Of course, these statements also apply to future or future marketed plant varieties with these or future developed genetic traits.
• the plants listed can be treated particularly advantageously according to the invention with the compounds of general formula (I) or the Wirkstoffrnischungen invention.
• the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants.
• Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
• the specified logP values were determined according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.
• Eluents for determination in the acidic range (pH 2.3): 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.
• the calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose LogP values are known (determination of the LogP values by means of the retention times by linear interpolation between two consecutive alkanones).
• the lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
• Solvent 24.5 parts by weight acetone 24.5 parts by weight dimethyl acetamide emulsifier: 1 part by weight alkyl aryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the indicated 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 about 21 ° C and a relative humidity of about 90%.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
• the plants are then placed in a greenhouse at a temperature of about 20 ° C and a relative humidity of 80% to promote the development of rust pustules.

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