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EP1648890A2 - Aryl-condensed 3-arylpyridine compounds and use thereof for controlling pathogenic fungi - Google Patents

Aryl-condensed 3-arylpyridine compounds and use thereof for controlling pathogenic fungi

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Publication number
EP1648890A2
EP1648890A2 EP04763272A EP04763272A EP1648890A2 EP 1648890 A2 EP1648890 A2 EP 1648890A2 EP 04763272 A EP04763272 A EP 04763272A EP 04763272 A EP04763272 A EP 04763272A EP 1648890 A2 EP1648890 A2 EP 1648890A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
compounds
halogen
haloalkyl
hydrogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04763272A
Other languages
German (de)
French (fr)
Inventor
Oliver Wagner
Thomas Grote
Carsten Blettner
Markus Gewehr
Wassilios Grammenos
Andreas Gypser
Bernd Müller
Joachim Rheinheimer
Peter Schäfer
Frank Schieweck
Anja Schwögler
Jordi Tormo I Blasco
Alan Akers
John-Bryan Speakman
Michael Rack
Reinhard Stierl
Maria Scherer
Siegfried Strathmann
Ulrich Schöfl
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1648890A2 publication Critical patent/EP1648890A2/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to new, aryl-condensed 3-aryipyridine compounds and their use for controlling harmful fungi and crop protection agents which contain such compounds as an active ingredient.
  • EP-A 71792, US 5,994,360, EP-A 550113, WO 02/48151 describe fungicidally active pyrazolo [1, 5-a] pyrimidines and triazolo [1, 5a] pyrimidines which in the 5-position of the pyrimidine ring optionally substituted one Wear phenyl group.
  • WO 03/022850 discloses imidazolo [1, 2-a] pyrimidines with a fungicidal action.
  • New active ingredients should kill the harmful fungi at the lowest possible application rates and reduce or even prevent them from forming again.
  • the active ingredients should have good crop tolerance, i.e. H. do not harm the crop plants or only do so to a small extent.
  • 111, 2813-2824 (1978) are 4-hydroxy-3- (4-methoxyphenyl) -1, 8-naphthyridin-2 (1 H) -one; 4-hydroxy-3- (4-methylphenyl) -1, 8-naphthyridin-2 (1 H) -one, 4-hydroxy-3- (3-methylphenyl) -1, 8-naphthyridin-2 (1 H) - on and 4-hydroxy-3- (2-methylphenyl) -, 8-naphthyridin-2 (1 H) -one known.
  • the object of the present invention is therefore to provide new compounds with good fungicidal activity, in particular with low application rates and / or good crop tolerance.
  • This object is achieved by bicyclic, ie aryl-fused 3-arylpyridine compounds of the general formula I
  • X, Y are independently N or CR 4 ; n represents 1, 2, 3, 4 or 5;
  • R a is halogen, cyano, CC 6 alkyl, C r C 6 alkoxy, haloalkyl CC 6, CC 6 - haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy or C (O) R 5 stands;
  • R 1 halogen, cyano, CC 6 alkyl, CrC-e-haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, optionally with alkyl and / or halogen - or is multiply substituted, C 5 -C 8 cycloalkenyl, which is optionally mono- or polysubstituted with alkyl and / or halogen, is OR 6 , SR 6 or NR 7 R 8 ;
  • R 2 halogen, cyano, CC 6 alkyl, CC 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, which may be substituted with alkyl and / or halogen or is multiply substituted, Cs-C ⁇ -cycloalkenyl, which is optionally mono- or polysubstituted by alkyl and / or halogen, is OR 6 , SR 6 or NR 7 R 8 ;
  • R 3 represents hydrogen, CC 6 alkyl, CC 6 haloalkyl or C 3 -C 6 cycloalkyl, which is optionally mono- or polysubstituted by alkyl and / or halogen;
  • R 4 represents hydrogen, halogen, Ct-C 6 alkyl, CC 6 haloalkyl or C 3 -C 6 cycloalkyl, which is optionally mono- or polysubstituted by alkyl and / or halogen;
  • R 5 is hydrogen, OH, CRCE alkyl, CC 6 alkoxy, CC 6 haloalkyl, -C 6 - haloalkoxy, C 2 -C 6 alkenyl, CC 6 alkylamino or di-CrC 6 alkylamino, piperidin-1-yl , Pyrrolidin-1-yl or morpholin-4-yl;
  • R 6 is hydrogen, CC 6 -alkyl, CrCe-haloalkyl, phenyl-C C -alkyl, where phenyl can be mono- or polysubstituted by halogen, alkyl or alkoxy, is C 2 -C 6 -alkenyl or COR 9 ;
  • R 7 , R 8 independently of one another for hydrogen, C -C 0 alkyl, C 2 -C 10 alkenyl, C 4 - C 10 alkadienyl, C 2 -C 10 alkynyl, C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, C 5 -C 10 bicycloalkyl, phenyl, phenyl-C C 4 alkyl, naphthyl, a 5- or 6-membered, saturated or partially unsaturated heterocycle, which may have 1, 2 or 3 heteroatoms, selected from N, O and S, as ring members, or a 5- or 6-membered aromatic heterocycle, which Can have 1, 2 or 3 hetero atoms, selected from N, O and S, as ring members, it being possible for the radicals mentioned as R 7 , R 8 to be partially or completely halogenated and / or to have 1, 2 or 3 radicals R b can, wherein R b is selected from cyano
  • the compounds I are new with the exception of those described in US Pat. No. 5,801,183, WO 96/22990, in J. of Heterocyclic Chemistry, 30, 1993, 909-912 and in Chem. Ber. 111, 2813-2824 (1978) called 1,8-naphthyridines. Accordingly, the present invention also relates to bicyclic compounds of the general formula I and their agriculturally acceptable salts, with the exception of: compounds of the general formula I in which R 1 is OH when Y and X are each CR 4 ; and - 2,4-dichloro-3- (o-methoxyphenyl) -1, 8-naphthyridine.
  • the present invention furthermore relates to an agent for combating harmful fungi, comprising at least one compound of the general formula I. and / or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.
  • the compounds of the formula I can have one or more centers of chirality and are then present as pure enantiomers or diastereomers or as enantiomer or diastereomer mixtures.
  • the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
  • the invention also relates to tautomers of compounds of the formula I.
  • Agriculturally useful salts include, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the fungicidal activity of the compounds I.
  • cations in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which if desired one to four C ⁇ -C 4 alkyl substituents and / or can carry a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 -alkyl) sulfonium and preferably sulfoxonium ions Tri (
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of CrC ⁇ alkanoic acids, preferably formate and butyrate. They can be formed by reacting I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • Halogen fluorine, chlorine, bromine and iodine
  • Haloalkyl straight-chain or branched alkyl groups with 1 to 4 or to 6 carbon atoms (as mentioned above), it being possible for part or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, Bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trich
  • Phenyl -CC-C 4 alkyl for a substituted by phenyl - as mentioned above - substituted CC 4 alkyl group, for. B. for benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1 -yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl , 1- (phenylmeth) -eth-1-yl, 1- (phenylmethyl) -1- (methyl) -eth-1-yl or - (phenylmethyl) -1- (methyl) -prop-1-yl; preferably benzyl;
  • Phenyl-CrC ⁇ alkyl which is optionally mono- or polysubstituted by halogen, alkoxy or alkyl: a phenyl-substituted CrC -alkyl group, the phenyl group being unsubstituted or 1, 2, 3 or 4, preferably 1, substituents selected from Fluorine, chlorine, bromine, dC 6 alkoxy or -CC 6 alkyl, can carry, for. B. for p-bromophenylmethyl, p-chlorophenylmethyl, p-methylphenylmethyl, p-methylphenylmethyl, p-methoxyphenylmethyl, p-methoxyphenylethyl;
  • Alkenyl monounsaturated, straight-chain or branched hydrocarbon radicals with 2 to 4, to 6 to 8 or to 10 carbon atoms and a double bond in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1 - Methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl , 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2 -butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-di
  • Alkadienyl double-unsaturated, straight-chain or branched hydrocarbon radicals with 4 to 10 carbon atoms and two double bonds in any position, e.g. 1, 3-butadienyl, 1-methyl-1,3-butadienyl, 2-methyl-1, 3-butadienyl, penta-1,3-dien-1-yl, hexa-1,4-dien-1-yl, Hexa-1,4-dien-3-yl, hexa-1, 4-dien-6-yl, hexa-1,5-dien-1-yl, hexa-1, 5-dien-3-yl, hexa- 1, 5-dien-4-yl, hepta-1,4-dien-1-yl, hepta-1, 4-dien-3-yl, hepta-1,4-dien-6-yl, hepta-1, 4-dien-3-yl, hepta-1,4-dien-6-yl, h
  • Alkynyl straight-chain or branched hydrocarbon groups with 2 to 4, 2 to 62 to 8 or 2 to 10 carbon atoms and a triple bond in any position, for example C 2 -C 6 -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1- Butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2
  • Cycloalkyl which is optionally mono- or polysubstituted by halogen or alkyl: a - as mentioned above - unsubstituted or 1, 2, 3 or 4, preferably 1, substituent-bearing cycloalkyl group, the substituents being selected from fluorine, chlorine, bromine or CC 6 alkyl, e.g.
  • substituents being selected from fluorine, chlorine, bromine or CC 6 alkyl, e.g.
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups with 5 to 8, preferably up to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl and cyclohexen-4-yl;
  • Cycloalkenyl which is optionally mono- or polysubstituted by halogen or alkyl: a - as mentioned above - unsubstituted or 1, 2, 3 or 4, preferably 1, substituent-bearing cycloalkenyl group, the substituents being selected from fluorine, chlorine, bromine or CC 6 alkyl, e.g. B.
  • Bicycloalkyl bicyclic hydrocarbon radical with 5 to 10 carbon atoms, such as bicyclo [2.2.1] hept-1-yl, bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.1] hept-7-yl, Bicyclo [2.2.2] oct-1-yl, bicyclo [2.2.2] oct-2-yl, bicyclo [3.3.0] octyl and bicyclo [4.4.0] decyl.
  • CrC 4 alkoxy for an oxygen-bonded alkyl group having 1 to 4 carbon atoms z. B. methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
  • Ci-Ce alkoxy for CC 4 alkoxy, as mentioned above, and z.
  • B pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3- Methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-
  • C ⁇ -C 6 haloalkoxy for CC 4 haloalkoxy, as mentioned above, and for example 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy , 6-iodohexoxy or dodecafluorohexoxy;
  • Alkenyloxy alkenyl as mentioned above, which is bonded via an oxygen atom, for example C 2 -C 6 alkenyloxy such as vinyloxy, 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1 -Methyl-1-propeny!
  • Alkynyloxy alkynyl as mentioned above which is bonded via an oxygen atom, for example C 3 -C 6 -alkynyloxy such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy , 4-pentynyloxy, 1-methyl-2-butynyloxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy, 5 -Hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl-3-pentynyloxy and the like;
  • heterocyclyl containing, in addition to carbon ring members, one to three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl Isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-ox
  • a first preferred embodiment of the present invention relates to compounds of the formula I in which X and Y each represent CR 4 , where R 4 can each be the same or different. These compounds are referred to below as compounds a.
  • connections 1b Another preferred embodiment of the present invention relates to compounds of the formula I in which X is CR 4 and Y is N. These connections are referred to below as connections 1b.
  • Another preferred embodiment of the present invention relates to compounds of the formula I in which X is N and Y is CR 4 . These connections are referred to below as connections lc.
  • variables n, R a , R 1 , R 2 , R 3 and R 4 have the following meanings independently of one another and preferably in combination:
  • R a halogen, in particular fluorine or chlorine, CrC 4 -alkyl, in particular methyl, CC 4 -alkoxy, in particular methoxy, CrC 2 -fluoroalkyl, in particular difluoromethyl and trifluoromethyl, CrC 2 -fluoroalkoxy, in particular difluoromethoxy and trifluoromethoxy, CrC 4 - Alkoxycarbonyl, especially methoxycarbonyl and cyano ;
  • R a is particularly preferably selected from halogen, especially fluorine or chlorine, CrC 4 alkyl, especially methyl, and CC alkoxy, especially methoxy;
  • R 1 halogen, especially chlorine, hydroxy or a group NR 7 R 8 ;
  • R 2 halogen, especially chlorine, hydroxy, CrC 6 alkyl, especially methyl; CrC 6 haloalkyl or a group NR'R;
  • R 3 is hydrogen, CrCe-alkyl, preferably CrC 3 -alkyl, CrCe-haloalkyl, preferably CrC 3 -haloalkyl, and particularly preferably hydrogen;
  • R 4 is hydrogen, halogen, CC 6 alkyl, preferably CrC 3 alkyl, CrCe haloalkyl, preferably CrC 3 haloalkyl, and particularly preferably hydrogen. If R 1 is halogen, especially chlorine, R 2 is preferably halogen, especially chlorine, CrCe-alkyl, especially methyl, CrC 6 -haloalkyl or a group NR 7 R 8 .
  • R 1 is hydroxy
  • R 2 is preferably hydroxy, CC 6 alkyl or C Ce-haloalkyl.
  • R 1 represents a group NR 7 R 8
  • R 2 is preferably selected from halogen, especially chlorine, CC 6 alkyl, especially methyl, and -C 6 haloalkyl.
  • R 1 is a group NR 7 R 8
  • at least one of the radicals R 7 , R 8 is preferably different from hydrogen.
  • R 7 represents CrC 6 alkyl.
  • C 3 -C 8 cycloalkyl which is optionally mono- or polysubstituted with alkyl, CrCe-haloalkyl, phenyl-CrC 4 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl.
  • R 8 stands in particular for hydrogen, CrC 6 alkyl or C 2 -C 6 alkenyl and very particularly preferably for hydrogen and CC 4 alkyl.
  • the preferred groups NR 7 R 8 also include those which represent a saturated or partially unsaturated heterocyclic radical which, in addition to the nitrogen atom, can have a further heteroatom selected from O, S and NR 10 as a ring member, and one or two May have substituents which are selected from halogen, hydroxy, CrC 6 alkyl and CC 6 haloalkyl.
  • the heterocyclic radical preferably has 5 to 7 atoms as ring members. Examples of such heterocyclic radicals are pyrrolidine, piperidine, morpholine, tetrahydropyridine, for example 1, 2,3,6 tetrahydropyridine, piperazine and azepane, which can be substituted in the aforementioned manner.
  • R 2 represents a group NR 7 R 8
  • at least one of the radicals R 7 , R 8 is preferably different from hydrogen.
  • R 7 has the meanings previously mentioned as preferred.
  • R a examples include halogen, especially F or Cl, trifluoromethyl,
  • the rest is preferably a radical of the formula
  • R a1 has the meanings given above for R a and the radicals R a2 , R a3 , R a4 and R a5 have the meanings indicated for R a or are hydrogen.
  • R a1 has the meanings given above for R a and the radicals R a2 , R a3 , R a4 and R a5 have the meanings indicated for R a or are hydrogen.
  • R a1 for fluorine, chlorine, trifluoromethyl or methyl
  • R a2 for hydrogen or fluorine
  • R a3 for hydrogen, fluorine, chlorine, cyano, C 1 -C 4 alkyl, especially methyl, CC alkoxy, especially methoxy or CC 4 alkoxycarbonyl, especially methoxycarbonyl;
  • R a4 for hydrogen, chlorine or fluorine;
  • R a5 for hydrogen, fluorine, chlorine or CC 4 -alkyl, especially methyl, or CrC 4 -alkoxy, especially methoxy.
  • At least one of the radicals R a3 or R a5 is preferably different from hydrogen.
  • a preferred embodiment of the compounds of the invention are those wherein R 2 is halo, cyano, -C 6 alkyl, CrC 6 -HalogenaIkyl, C 2 -C 6 alkenyl, C 2 lb - C 6 alkynyl C 3 -C 8 cycloalkyl , which is optionally mono- or polysubstituted with alkyl and / or halogen, C 5 -C 8 cycloalkenyl which is optionally monosubstituted or polysubstituted with alkyl and / or halogen, or NR 7 R 8 , in which R 7 and R 8 are each different from hydrogen.
  • La and lc relates to those, wherein R 2 is halogen, cyano, -C 6 alkyl, -C 6 haloalkyl, C 2 - Ce alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 -Cycloalkyl, which is optionally mono- or polysubstituted with alkyl and / or halogen, C 5 -C 8 -cycloalkenyl, which is mono- or polysubstituted or substituted with alkyl and / or halogen, OR 6 , SR 6 or NR 7 R 8 means in which R 6 , R 7 and R 8 have the abovementioned and in particular the preferred meanings.
  • R 3 , R 4 , R 5 and R 6 are independent of one another and preferably in combination with the preferred meanings of the variables n, R a , R 1 and R 2 have the following meanings:
  • R 3 is hydrogen, -C 6 alkyl, preferably -C 3 alkyl, -C 6 haloalkyl, preferably -C 3 haloalkyl, and particularly preferably hydrogen;
  • R 4 is hydrogen, CC 6 alkyl, preferably CC 3 alkyl, -C 6 haloalkyl, preferably -C 3 haloalkyl, and particularly preferably hydrogen;
  • R 5 is hydrogen, CC 4 alkyl or CC 4 alkoxy
  • R 6 is hydrogen, CC 4 alkyl, benzyl or CC 4 alkyl carbonyl.
  • Particularly preferred compounds of the general formula I with regard to use as a fungicide are the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2-methyl-4-chlorine (compounds la1, lblund lc1). Examples of these are compounds la1, lblund lc1, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds la1, lblund lc1, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds la1, lblund lc1, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds la1, lblund lc1, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la1, lblund lc1, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-fluoro-4-methyl (compounds la2, lb2 and lc2).
  • Examples include compounds LA2, LB2 and LC2, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds la2, lb2 and lc2, in which R 2 and R 1 are each chlorine. Examples of these are also compounds la2, lb2 and lc2, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds la2, lb2 and lc2, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la2, lb2 and lc2, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,6-dimethyl (compounds la3, lb3 and lc3).
  • R 3 and R 4 are each hydrogen
  • R 2 is hydroxyl
  • chlorine or methyl and (R a ) n stands for 2,6-dimethyl
  • R 3 and R 4 are each hydrogen
  • R 2 is hydroxyl, chlorine or methyl
  • (R a ) n stands for 2,6-dimethyl
  • Examples of these are also compounds la3, lb3 and lc3, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la3, lb3 and lc3, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,4,6-trimethyl (compounds la4, lb4 and lc4).
  • R 3 and R 4 are each hydrogen
  • R 2 is hydroxyl
  • chlorine or methyl and (R a ) n stands for 2,4,6-trimethyl
  • compounds la4, lb4 and lc4 examples of these are compounds la4, lb4 and lc4, in which R 2 and R 1 each represent hydroxy.
  • Examples of these are also compounds la4, lb4 and lc4, in which R 2 and R 1 are each chlorine.
  • Examples of these are also compounds la4, lb4 and lc4, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds LA4, LB4 and LC4, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together have the meanings given in one row of Table A.
  • Examples of these are also compounds la4, lb4 and lc4, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2,6-difluoro-4-methyl (compounds la5, lb5 and lc5).
  • Examples include compounds LA5, LB5 and LC5, in which R 2 and R 1 each represent hydroxy. Examples of this are also compounds LA5, LB5 and LC5, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds la5, lb5 and lc5, in which R 2 is methyl and R is chlorine.
  • Examples of these are also compounds la5, lb5 and lc5, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Examples of these are also compounds LA5, LB5 and LC5, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,6-difluoro-4-cyano (compounds la6, lb6 and lc6).
  • Examples include compounds LA6, LB6 and LC6, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA6, LB6 and LC6, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds la6, lb6 and lc6, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds la6, lb6 and lc6, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Examples of these are also compounds LA6, LB6 and LC6, in which R 2 is methyl and R is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2,6-difluoro-4-methoxycarbonyl (compounds la7, lb7 and lc7).
  • Examples of these are compounds LA7, LB7 and LC7, in which R 2 and R 1 each represent hydroxy.
  • Examples of these are also compounds LA7, LB7 and LC7, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds la7, lb7 and lc7, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds la7, lb7 and lc7, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Examples of these are also compounds LA7, LB7 and LC7, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicide are also the compounds of the general formulas a, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-trifluoromethyl-4-fluorine (compounds la8, lb8 and lc8).
  • R 3 and R 4 are each hydrogen
  • R 2 is hydroxyl
  • chlorine or methyl methyl
  • (R a ) n is 2-trifluoromethyl-4-fluorine
  • Examples of these are also compounds LA8, LB8 and LC8, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA8, LB8 and LC8, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-trifluoromethyl-5-fluorine (compounds la9, lb9 and lc9).
  • Examples include compounds LA9, LB9 and LC9, in which R 2 and R 1 each represent hydroxy.
  • Examples of these are also compounds LA9, LB9 and LC9, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds LA9, LB9 and LC9, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds la9, lb9 and lc9, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la9, lb9 and lc9, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n represents 2-trifluoromethyl-5-chlorine (compounds LA10, LB10 and LC10).
  • compounds LA10, LB10 and LC10 in which R 2 and R 1 each represent hydroxy.
  • examples of these are also compounds LA10, LB10 and LC10, in which R 2 and R 1 each represent chlorine. Examples of this are also fertilize la10, lb10 and lc10, where R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds LA10, LB10 and LC10, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA10, LB10 and LC10, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-chloro-6-fluorine (compounds la11, lb11 and lc11).
  • Examples include compounds LA11, LB11 and LC11, in which R 2 and R 1 each represent hydroxy.
  • examples of these are also compounds LA11, LB11 and LC11, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds la11, lb11 and lc11, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds la11, lb11 and lc11, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la11, lb11 and lc11, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,6-difluoro (compounds la12, Lb.12 and lc12).
  • Examples include compounds LA12, Lb.12 and LC12, in which R 2 and R 1 each represent hydroxy.
  • examples of these are also compounds LA12, Lb.12 and LC12, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds LA12, Lb.12 and LC12, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds LA12, Lb.12 and LC12, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Examples of these are also compounds LA12, Lb.12 and LC12, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as a fungicide are also the compounds of the general formula La, Ib and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxy, chlorine or methyl and (R a ) n is 2,6-dichloro (compounds la13, lb13 and lc13).
  • Examples include compounds LA13, LB13 and LC13, in which R 2 and R 1 each represent hydroxy.
  • Examples of these are also compounds LA13, LB13 and LC13, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds LA13, LB13 and LC13, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds LA13, LB13 and LC13, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Examples of these are also compounds LA13, LB13 and LC13, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-fluoro-6-methyl (compounds la14, lb14 and lc14).
  • Examples of these are compounds LA14, LB14 and LC14, in which R 2 and R 1 each represent hydroxy.
  • Examples of these are also compounds LA14, LB14 and LC14, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds LA14, LB14 and LC14, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds LA14, LB14 and LC14, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA14, LB14 and LC14, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,4,6-trifluoro (compounds la15, lb15 and lc15).
  • Examples include compounds LA15, LB15 and LC15, in which R 2 and R 1 each represent hydroxy.
  • Examples of these are also compounds LA15, LB15 and LC15, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds LA15, LB15 and LC15, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds LA15, LB15 and LC15, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Examples of these are also compounds LA15, LB15 and LC15, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2,6-difluoro-4-methoxy (compounds La.16, LB16 and LC16).
  • Examples include compounds LA16, LB16 and LC16, in which R 2 and R 1 each represent hydroxy.
  • examples of these are also compounds LA16, LB16 and LC16, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds LA16, LB16 and LC16, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds LA16, LB16 and LC16, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Examples of these are also compounds LA16, LB16 and LC16, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to use as a fungicide are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2,3,4,5,6-pentafluoro (compounds la17, lb17 and lc17).
  • Examples include compounds LA17, LB17 and Lc.17, in which R 2 and R 1 each represent hydroxy.
  • examples of these are also compounds LA17, LB17 and LC17, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds LA17, LB17 and LC17, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds LA17, LB17 and Lc.17, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Examples of these are also compounds la17, lb17 and Lc.17, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-methyl-4-fluorine (compounds la18, lb18 and lc18).
  • Examples include compounds LA18, LB18 and LC18, in which R 2 and R 1 each represent hydroxy.
  • Examples include compounds LA18, LB18 and LC18, in which R 2 and R 1 each represent chlorine.
  • Examples include connections gen la18, lb18 and lc18, wherein R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds la18, lb18 and lc18, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la18, lb18 and lc18, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicide are also the compounds of the general formulas a, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-fluoro-6-methoxy (compounds La.19, lb19 and lc19).
  • Examples include compounds LA19, LB19 and LC19, in which R 2 and R 1 each represent hydroxy.
  • Examples include compounds LA19, LB19 and LC19, in which R 2 and R 1 each represent chlorine.
  • Examples include compounds LA19, LB19 and LC19, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds LA19, LB19 and LC19, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Examples of these are also compounds la19, lb19 and lc19, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,4-difluoro (compounds LA20, LB20 and LC20).
  • compounds LA20, LB20 and LC20 in which R 2 and R 1 each represent hydroxy.
  • examples of these are also compounds LA20, LB20 and LC20, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds LA20, LB20 and LC20, in which R 2 is methyl and R is chlorine.
  • Examples of these are also compounds LA20, LB20 and LC20, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA20, LB20 and LC20, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as a fungicide are also the compounds of the general formula a, Ib and lc, where R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-fluoro-4-chlorine (compounds la21, lb21 and lc21).
  • Examples include compounds LA21, LB21 and LC21, in which R 2 and R 1 each represent hydroxy.
  • examples of these are also compounds LA21, LB21 and LC21, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds LA21, LB21 and LC21, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds LA21, LB21 and LC21, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Examples of these are also compounds la21, lb21 and lc21, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-chloro-4-fluorine (compounds la22, lb.22 and lc22).
  • Examples include compounds LA22, Lb.22 and LC22, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA22, Lb.22 and LC22, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA22, Lb.22 and LC22, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds LA22, Lb.22 and LC22, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Examples of these are also compounds LA22, Lb.22 and LC22, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,3-difluoro (compounds la23, lb23 and Lc.23).
  • R 3 and R 4 are each hydrogen
  • R 2 is hydroxyl
  • chlorine or methyl and (R a ) n stands for 2,3-difluoro
  • Examples of these are compounds la23, lb23 and Lc.23, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds la23, lb23 and Lc.23, in which R 2 and R 1 are each chlorine. Examples of these are also compounds la23, lb23 and Lc.23, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds la23, lb23 and Lc.23, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la23, lb23 and Lc.23, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,5-difluoro (compounds la24, lb24 and lc24).
  • Examples include compounds LA24, LB24 and LC24, in which R 2 and R 1 each represent hydroxy.
  • Examples of these are also compounds LA24, LB24 and LC24, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds LA24, LB24 and LC24, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds LA24, LB24 and LC24, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA24, LB24 and LC24, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,3,4-trifluoro (compounds la25, lb25 and lc25).
  • Examples include compounds LA25, LB25 and LC25, in which R 2 and R 1 each represent hydroxy.
  • examples of these are also compounds LA25, LB25 and LC25, in which R 2 and R 1 each represent chlorine.
  • Examples of these are also compounds la25, lb25 and lc25, in which R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds la25, lb25 and lc25, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la25, lb25 and lc25, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n represents 2,4-dimethyl (compounds la26, lb26 and lc26).
  • Examples include compounds LA26, LB26 and LC26, in which R 2 and R 1 each represent hydroxy.
  • Examples of these are also compounds LA26, LB26 and LC26, in which R 2 and R 1 each represent chlorine. Examples of this are connections la26, lb26 and lc26, wherein R 2 is methyl and R 1 is chlorine.
  • Examples of these are also compounds la26, lb26 and lc26, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la26, lb26 and lc26, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
  • R stands for CC 4 -alkyl, in particular for methyl or ethyl
  • W stands for CrCe-alkyl, C Ce-alkoxy, in particular for methoxy or ethoxy, CrC 6 -haloalkyl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted C 5 -C 8 cycloalkenyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl
  • U represents OH, CrCe alkyl, CC 6 haloalkyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted C 5 -C 8 cycloalkenyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl.
  • a hetarylamine of the general formula II is condensed with a CH-acidic compound of the general formula III in a first step.
  • suitable CH-acidic compounds of the general formula III are substituted phenylacetic acid (CrC 4 ) alkyl esters and substituted benzyl (halogen) alkyl ketones, benzyl cycloalkyl ketones, benzylalkenyl ketones, benzylcycloalkenyl ketones and benzylalkynyl ketones.
  • hetarylamines of the general formula II are 2-amino pyridine-3-carboxylic acid ester (2-aminonicotinic acid ester), 3-aminopyrazine-2-carboxylic acid ester and 4-aminopyrimidine-5-carboxylic acid ester.
  • the condensation is usually carried out in the presence of a Brönstedt or Lewis acid as an acid catalyst or in the presence of a basic catalyst, see e.g. B. Organikum, 15th edition, VEB German Publishing House of Sciences, Berlin 1976, 552ff.
  • a basic catalyst see e.g. B. Organikum, 15th edition, VEB German Publishing House of Sciences, Berlin 1976, 552ff.
  • suitable acidic catalysts are zinc chloride, phosphoric acid, hydrochloric acid, acetic acid and mixtures of acetic acid and zinc chloride.
  • suitable basic catalysts are inorganic and organic basic catalysts.
  • Suitable inorganic basic catalysts are, for example, alkali or alkaline earth metal hydrides, preferably alkali metal hydrides such as sodium hydride or potassium hydride and alkali and alkaline earth metal hydroxides such as sodium hydroxide or potassium hydroxide. Furthermore, the condensation can be carried out in the presence of metallic sodium when using substituted phenylacetic acid ester.
  • Suitable organic basic catalysts are alkali metal or alkaline earth metal alkoxides such as sodium methylate, sodium ethylate, sodium n-propylate, sodium isopropylate, sodium n-butoxide, sodium sec-butoxide, sodium tert-butoxide, potassium methylate, potassium ethylate, potassium n-propylate, potassium isopropylate, potassium n-butoxide, potassium sec-butoxide, potassium tert-butoxide, secondary amines such as ethyldiisopropylamine and amidine bases such as 1,5-diazabicyclo- [4.3.0] non-5-ene ( DBN) or 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU).
  • alkali metal or alkaline earth metal alkoxides such as sodium methylate, sodium ethylate, sodium n-propylate, sodium isopropylate, sodium n-butoxide, sodium sec
  • the reaction can be carried out in the absence of a solvent or in a solvent.
  • the CH-acidic compound III is generally used in excess, based on the hetarylamine.
  • the OH group (s) in these compounds can be converted into other functional groups in one or more steps. As a rule, the OH group (s) will first be converted into halogen, especially chlorine (see Scheme 1a).
  • Suitable halogenating agents are phosphorus trihalides, phosphorus oxyhalides or phosphorus pentahalides, such as phosphorus tribromide, phosphorus oxytribromide, and in particular chlorinating agents, such as POCI 3 , PC C ⁇ 2 or PCI 5 , and mixtures of these reagents.
  • chlorinating agents such as POCI 3 , PC C ⁇ 2 or PCI 5 , and mixtures of these reagents.
  • a mixture of phosphorus pentachloride and phosphorus oxychloride is preferably used for the chlorination.
  • the reaction can occur in excess halogenating agent (POCI 3 ) or an inert solvent such as acetonitrile or 1, 2-dichloroethane.
  • reaction usually takes place between 10 and 180 ° C.
  • reaction temperature often corresponds to the boiling point of the chlorinating agent (POCI 3 ) or solvent used.
  • POCI 3 chlorinating agent
  • the process is optionally carried out with the addition of N, N-dimethylformamide or nitrogen bases, such as N, N-dimethylaniline in catalytic or stoichiometric amounts.
  • This method is known in principle, for example from II Farmaco, 57, 2002, 631, and can be used in an analogous manner for the preparation of the compounds according to the invention.
  • Protic solvents such as alcohols, for example ethanol, and aprotic solvents, for example aromatic hydrocarbons, halogenated hydrocarbon and ethers, for example toluene, o-, m- and p-xylene, diethyl- ether, diisopropyl ether, tert-butyl methyl ether, dioxane, tetrahydrofuran, dichloromethane, and mixtures of the abovementioned solvents.
  • aromatic hydrocarbons for example aromatic hydrocarbons, halogenated hydrocarbon and ethers, for example toluene, o-, m- and p-xylene, diethyl- ether, diisopropyl ether, tert-butyl methyl ether, dioxane, tetrahydrofuran, dichloromethane, and mixtures of the abovementioned solvents.
  • halogenated hydrocarbon and ethers for example toluen
  • Suitable auxiliary bases are, for example, those mentioned below: alkali metal carbonates and hydrogen carbonates such as NaHCO 3 and Na 2 CO 3 , alkali metal hydrogen phosphates such as Na 2 HPO 4 , alkali metal borates such as Na 2 B 4 O 7 , tertiary amines such as triethylamine, ethyldiisopropylamine or diethylaniline and pyridine compounds. An excess of the amine HNR 7 R 8 can also be used as an auxiliary base.
  • the components are usually used in an approximately stoichiometric ratio. However, it may be advantageous to use the amine HNR 7 R 8 in excess. If an excess of amine HNR 7 R 8 is used , the amine can simultaneously act as a solvent.
  • the amines HNR 7 R 8 are commercially available or known from the literature or can be prepared by known methods.
  • Suitable bases are alkali metal hydrides such as sodium hydride or potassium hydride, alkali or alkaline earth metal alkoxides such as sodium t-butoxide or potassium tert-butoxide or tertiary amines such as triethylamine or pyridine.
  • the alcohol R 6 OH can first be reacted with an alkali metal, preferably sodium, to form the corresponding alcoholate.
  • the reaction can be carried out in excess alcohol or in an inert solvent such as carboxamides, for example N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone.
  • the reaction is usually carried out at 0 ° C to 150 ° C, preferably at 10 ° C to 100 ° C.
  • step a) can be carried out in a manner known per se, for example in analogy to the method given in scheme 1b.
  • the ether linkage can be catalyzed by hydrogenolysis, e.g. B. split according to the method described in Org. Lett., 3, 2001, 4263.
  • Suitable catalysts are, for example, noble metals or transition metals such as palladium or platinum. As a rule, the catalyst is supported, for example on activated carbon. Hydrogenolysis is usually carried out in a solvent.
  • Suitable solvents are, for example, alcohols such as methanol or cyclic ethers such as tetrahydrofuran or dioxane.
  • Hydrogenolysis takes place at normal pressure. Hydrogenolysis is generally carried out at temperatures between room temperature and the boiling point of the solvent, preferably at temperatures between room temperature and 40 ° C.
  • Methods for converting alcohols into the corresponding halides are known from the prior art, e.g. B. from J. Chem. Soc. 1947, 899.
  • Suitable halogenating agents are, for example, the aforementioned halogenating agents (see scheme 1a).
  • the reaction can be carried out in excess halogenating agent, for example POCI 3 , or in an inert solvent such as acetonitrile or 1,2-dichloroethane.
  • the reaction is usually carried out between 10 and 180 ° C, preferably between room temperature and 130 ° C.
  • R 2 Cl ⁇ in compounds of formula I, wherein R 2 is -C 6 alkyl, -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 - C 6 -alkynyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted C 5 -C 8 cycloalkenyl, can be achieved in a manner known per se by reaction with organometallic compounds R 2a -Met, in which R 2a is CrC 6 alkyl, halo-CrC 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -alkynyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted C 5 -C 8 cycloalkenyl, and Met is lithium, Magnesium or zinc means.
  • the reaction is preferably carried out in the presence of catalytic or in particular at least equimolar amounts of transition metal salts and / or compounds, in particular in the presence of Cu salts such as Cu (l) halides and especially Cu (l) iodide.
  • the reaction takes place in an inert organic solvent, for example an ether, in particular tetrahydrofuran, an aliphatic or cycloaliphatic hydrocarbon such as hexane, cyclohexane and the like, an aromatic hydrocarbon such as toluene or in a mixture of these solvents.
  • the temperatures required for this are in the range of -100 to + 100 ° C and especially in the range of -80 ° C to + 40 ° C.
  • R 1 is CrC 6 alkyl, CrCe haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl or C 5 -C 8 -Cycloalkenyl
  • R 1a is C r C 6 -alkyl, CrC 6 Halogenoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, optionally substituted C 3 -C 8 cycloalkyl or optionally substituted C 5 - C 8 cycloalkenyl and Met stands for lithium, magnesium or zinc.
  • Hetarylamines of the general formula II are commercially available, known from the literature or can be prepared based on known processes from the literature, for. B. J. Chem. Soc. 1937, 367; J. Chem. Soc. 1953, 331; Bioorg. Med. Chem. 9, (2001) 2061; JACS 67, 1945, 1711.
  • Substituted phenylacetic acid esters of the general formula III are known from the literature or can be prepared based on known processes.
  • ketones of the general formula III are new, provided the rest
  • R a1 for fluorine, chlorine, trifluoromethyl or methyl
  • R a2 for hydrogen or fluorine
  • R a3 for hydrogen, fluorine, chlorine, cyano, CC 4 -alkyl, especially methyl, CC 4 -alkoxy, especially methoxy or CrC 4 -alkoxycarbonyl, especially methoxycarbonyl
  • R a4 for hydrogen, chlorine or fluorine
  • R a5 is hydrogen, fluorine, chlorine or C r C 4 alkyl, especially methyl, or CrC 4 alkoxy, especially methoxy.
  • the present invention thus also relates to ketones of the general formula IIID
  • R a1 , R a2 , R a3 , R a4 and R a5 have the meanings given above and
  • W is CrCe alkyl, CrC 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, which is optionally mono- or polysubstituted by alkyl and / or halogen, C 5 -C 8 cycloalkenyl, which is optionally mono- or polysubstituted with alkyl and / or halogen.
  • W ' is preferably CrC 6 alkyl, in particular methyl.
  • At least one of the radicals R a3 or R a5 is preferably different from hydrogen.
  • Preferably at least one and particularly preferably both radicals R a2 , R a4 are hydrogen.
  • (R a ) n is 2-CH 3 -4-CI, 2-F-4-CH 3 , 2,6-di-F-4-CH 3 , 2.6 -di-F-4-CN, 2,6-di-F-4- COOCH 3 , 2-CF 3 -4-F, 2-CF 3 -5-F, 2-CF 3 -5-CI, 2 -F-6-CH 3 , 2,6-di-F-4-OCH 3 , 2-CH 3 -4-F, 2-F-6-OCH 3, 2-F-4-CI, 2-C1 -4-F, 2,5-di-F, 2,4,6-tri-F or 2,3,4-tri-F.
  • ketones of the general formula III in particular the ketones of the general formula IIID, can be prepared, for example, according to scheme 2 by heating a phenyl- ⁇ -keto ester of the general formula IV in the presence of a weak aqueous acid, for example lithium chloride.
  • a weak aqueous acid for example lithium chloride.
  • R a and n have the meanings given above, in particular the meanings mentioned as preferred, W 'stands for C r Ce alkyl, CrC 6 haloalkyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted C 5 -C 8 - cycloalkenyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl.
  • compound IV is used as its ethyl ester.
  • the acid is used in excess, based on the phenyl- ⁇ -ketoester IV.
  • the phenyl- ⁇ -ketoester IV is usually heated in a solvent. Suitable solvents are dipolar aprotic solvents such as dimethyl sulfoxide.
  • the reaction temperature is usually in the range from room temperature to the boiling point of the solvent, preferably in the range from 60 ° C. to the boiling point of the solvent.
  • the phenyl- ⁇ -keto esters IV are either known from the literature, for example from WO 99/41255, or can be prepared based on known processes from the literature, for example based on Houben-Weyl, volume Vll / 2a, p. 521 become.
  • the compounds I are suitable as fungicides. They are characterized by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides.
  • the compounds I are also suitable for combating harmful fungi such as Pacilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • harmful fungi such as Pacilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds.
  • the application can take place both before and after the infection of the materials, plants or seeds by the fungi.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
  • amounts of active ingredient of 0.001 to 1 g, preferably 0.01 to 0.5 g, are generally required per kilogram of seed.
  • the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.
  • the compounds I can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, where, in the case of water as the diluent, other organic solvents can also be used as auxiliary solvents.
  • auxiliaries solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g.
  • Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates)
  • Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • Mineral oil fractions of medium to high boiling point such as kerosene are used to produce directly sprayable solutions, emulsions, pastes or oil dispersions.
  • sin or diesel oil also coal tar oils as well as oils of plant or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g.
  • benzene toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohe - xanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, for example dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, into consideration.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as grain flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral earths such as silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • V. 80 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene- ⁇ -sulfonic acid, 10 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and grind in a hammer mill (active ingredient content 80% by weight).
  • the active ingredients as such in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or Pouring can be applied.
  • the application forms depend entirely on the Twist purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, old dispersions) by adding water.
  • emulsions, pastes or old dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates composed of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • the active ingredient concentrations in the ready-to-use preparations can be varied over a wide range. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume process
  • Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
  • compositions according to the invention can also be present together with other active compounds which, e.g. with herbicides, insecticides, growth regulators, fungicides or also with fertilizers. Mixing the compounds I or the compositions containing them in the use form as fungicides with other fungicides results in an enlargement of the fungicidal spectrum of action in many cases.
  • Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,
  • Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine, tridemorph, Anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl,
  • Antibiotics such as cycioheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,
  • azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, Dinitroco- Nazole, epoxiconazole, fenbuconazole, Fluquiconazol, flusilazole, hexaconazole, I mazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, triadimefon, triadimenol, triflumizole, triticonazole .
  • Dicarboximides such as iprodione, myclozolin, procymidone, vinclozolin,
  • Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propinerb, Polycarbamat, Thiram, Ziram, Zineb,
  • Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, Dazomet, dithianon, famoxadone, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolan, mepronquin, probolene, probuene, nu- arifonil, probu- Pyroquilon, Quinoxyfen, Silthiofam, Thiabendazol, Thifluzamid, Thiophanat-methyl, Tiadinil, Tricyclazol, Triforine,
  • Copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate,
  • Nitrophenyl derivatives such as binapacryl, dinocap, dinobutone, nitrophthal-isopropyl,
  • Phenylpyrroles such as fenpiclonil or fludioxonil, sulfur,
  • fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chlorothalonil, cyflufenamid, cymoxanil, Dazomet, diclomezin, diclocymet, diethofencarb, edifenphos, ethaboxam, fenhexamide, fentin acetate, fenoxanil, fosetylamino, fefosetone, ferimosone, ferimzone Iprovalicarb, hexachlorobenzene, metrafenone, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintocene, zoxamide,
  • Strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin, • Sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid,
  • Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
  • the aqueous reaction mixture was extracted with ethyl acetate.
  • the organic layer was dried, the drying agent was filtered off and the mixture was evaporated to dryness, 8.6 g of ethyl 2,4,6-trifluorophenylacetate being recovered.
  • the aqueous phase was adjusted to pH 5.5 with acetic acid, a solid precipitating out. The precipitated solid was filtered off and dried to give 1.6 g (30%) of the title compound.
  • the reaction mixture was stirred from 0.12 g (0.3 mmol) of 7-benzyloxy-5-chloro-6- (2,4,6-trifluorophenyl) pyrido [2,3-d] pyrimidine from Example 3, 1.5 g of 4-methylpiperidine and 0.05 g of triethylamine for 3 hours at 80 ° C.
  • the reaction mixture was taken up in water and the aqueous mixture was washed three times with dichloromethane. After the combined organic phases had dried, the drying agent was filtered off and the filtrate was concentrated.
  • the active ingredients were prepared as a stock solution with 0.25% by weight of active ingredient in acetone or DMSO (dimethyl sulfoxide). 1% by weight of the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration.
  • DMSO dimethyl sulfoxide
  • Pots with wheat plants of the "Kanzler” variety were sprayed to runoff point with an aqueous suspension in the active compound concentration given below. At the the following day the pots were inoculated with an aqueous spore suspension of Leptosphaeria nodorum. The plants were then placed in a chamber at 20 ° C. and maximum air humidity. After 8 days, the leaf spot disease on the untreated but infected control plants had developed to such an extent that the infestation could be determined visually in%.

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Abstract

The invention relates to bicyclic compounds of general formula I, wherein X, Y independently represent N or C-R<4>; n stands for 1, 2, 3, 4 or 5; R<a >represents halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-halogenalkyl, C1-C6-halogenalkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy or C(O)R<5>; R<1> denotes halogen, cyano, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, optionally mono- or polysubstituted by alkyl and/or halogen, C5-C8 cycloalkenyl, optionally mono- or polysubstituted by alkyl and/or halogen, OR<6>, SR<6> or NR<7>R<8>; R<2> denotes halogen, cyano, C1-C6-alkyl, C1-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C8-cycloalkyl, optionally mono- or polysubstituted by alkyl and/or halogen, C5-C8-cycloalkenyl, optionally mono- or polysubstituted by alkyl and/or halogen, OR<6>, SR<6> or NR<7>R<8>, and R<3> represents hydrogen, C1-C6-alkyl, C1-C6-halogenalkyl or C3-C6-cycloalkyl, optionally mono- or polysubstituted by alkyl and/or halogen. Said invention also relates to the agriculturally-acceptable salts of said compounds (I), plant protection agents, containing at least one compound of general formula (I) and/or one agriculturally-acceptable salt of (I) and at least one liquid or solid carrier substance, as well as a method for controlling phytopathogenic fungi.

Description

Arylkondensierte 3-Arylpyridinverbindungen und ihre Verwendung zur Bekämpfung von SchadpilzenAryl-condensed 3-arylpyridine compounds and their use in combating harmful fungi
Beschreibungdescription
Die vorliegende Erfindung betrifft neue, arylkondensierte 3-AryIpyridinverbindungen und ihre Verwendung zur Bekämpfung von Schadpilzen sowie Pflanzenschutzmittel, die derartige Verbindungen als wirksamen Bestandteil enthalten.The present invention relates to new, aryl-condensed 3-aryipyridine compounds and their use for controlling harmful fungi and crop protection agents which contain such compounds as an active ingredient.
Die EP-A 71792, US 5,994,360, EP-A 550113, WO 02/48151 beschreiben fungizid wirksame Pyrazolo[1 ,5-a]pyrimidine und Triazolo[1 ,5a]pyrimidine, die in der 5-Position des Pyrimidinrings eine gegebenenfalls substituierte Phenylgruppe tragen. Aus der WO 03/022850 sind lmidazolo[1 ,2-a]pyrimidine mit fungizider Wirkung bekannt.EP-A 71792, US 5,994,360, EP-A 550113, WO 02/48151 describe fungicidally active pyrazolo [1, 5-a] pyrimidines and triazolo [1, 5a] pyrimidines which in the 5-position of the pyrimidine ring optionally substituted one Wear phenyl group. WO 03/022850 discloses imidazolo [1, 2-a] pyrimidines with a fungicidal action.
Prinzipiell besteht ein beständiger Bedarf an neuen fungizid wirksamen Verbindungen, um das Wirkungsspektrum zu verbreitern und um eine mögliche Resistenzbildung gegen bekannte Fungizide zu umgehen. Neue Wirkstoffe sollten die Schadpilze bei möglichst geringen Aufwandmengen abtöten und deren Neubildung verringern oder besser noch verhindern. Außerdem sollten die Wirkstoffe eine gute Nutzpflanzenverträglichkeit aufweisen, d. h. die Nutzpflanzen nicht oder nur in geringem Ausmaß schädigen.In principle, there is a constant need for new fungicidally active compounds in order to broaden the spectrum of action and to avoid possible formation of resistance to known fungicides. New active ingredients should kill the harmful fungi at the lowest possible application rates and reduce or even prevent them from forming again. In addition, the active ingredients should have good crop tolerance, i.e. H. do not harm the crop plants or only do so to a small extent.
Die US 5,801,183 und die WO 96/22990 beschreiben 2,4-Dihydraxy-1,8-naphthyridine, die in 3-Position einen gegebenenfalls substituierten Phenylrest tragen, als Aza- Analoge von Glycin/NMDA Rezeptor Antagonisten.No. 5,801,183 and WO 96/22990 describe 2,4-dihydraxy-1,8-naphthyridines which carry an optionally substituted phenyl radical in the 3-position as aza analogs of glycine / NMDA receptor antagonists.
Aus J. of Heterocyclic Chemistry, 30, 1993, 909 - 912 sind die Verbindungen 4- Hydroxy-3-(o-methoxyphenyl)-1 ,8-naphthyridin-2(1 H)-on und 2,4-Dichlor-3-(o- methoxyphenyl)-1 ,8-naphthyridin und aus Chem. Ber. 111, 2813 - 2824 (1978) sind 4-Hydroxy-3-(4-methoxyphenyl)-1 ,8-naphthyridin-2(1 H)-on; 4-Hydroxy-3-(4- methylphenyl)-1 ,8-naphthyridin-2(1 H)-on, 4-Hydroxy-3-(3-methylphenyl)-1 ,8- naphthyridin-2(1 H)-on und 4-Hydroxy-3-(2-methylphenyl)- ,8-naphthyridin-2(1 H)-on bekannt.From J. of Heterocyclic Chemistry, 30, 1993, 909-912 the compounds are 4-hydroxy-3- (o-methoxyphenyl) -1, 8-naphthyridin-2 (1 H) -one and 2,4-dichlor-3 - (o-methoxyphenyl) -1, 8-naphthyridine and from Chem. Ber. 111, 2813-2824 (1978) are 4-hydroxy-3- (4-methoxyphenyl) -1, 8-naphthyridin-2 (1 H) -one; 4-hydroxy-3- (4-methylphenyl) -1, 8-naphthyridin-2 (1 H) -one, 4-hydroxy-3- (3-methylphenyl) -1, 8-naphthyridin-2 (1 H) - on and 4-hydroxy-3- (2-methylphenyl) -, 8-naphthyridin-2 (1 H) -one known.
Im Hinblick auf mögliche Resistenzbildung und Verbreiterung des Wirkspektrums ist die Bereitstellung neuer Wirkstoffe grundsätzlich von Interesse.With regard to possible resistance formation and broadening of the spectrum of action, the provision of new active ingredients is of fundamental interest.
Der vorliegenden Erfindung liegt daher die Aufgabe zugrunde, neue Verbindungen mit guter fungizider Wirksamkeit, insbesondere bei geringen Aufwandmengen und/oder einer guten Nutzpflanzenverträglichkeit bereitzustellen. Diese Aufgabe wird durch bi- cyclische, d.h. arylkondensierte 3-Arylpyridinverbindungen der allgemeinen Formel I The object of the present invention is therefore to provide new compounds with good fungicidal activity, in particular with low application rates and / or good crop tolerance. This object is achieved by bicyclic, ie aryl-fused 3-arylpyridine compounds of the general formula I
gelöst, worinsolved where
X, Y unabhängig voneinander für N oder C-R4 stehen; n für 1 , 2, 3, 4 oder 5 steht;X, Y are independently N or CR 4 ; n represents 1, 2, 3, 4 or 5;
Ra für Halogen, Cyano, C C6-Alkyl, CrC6-Alkoxy, C C6-Halogenalkyl, C C6- Halogenalkoxy, C2-C6-Alkenyl, C2-C6-Alkenyloxy oder C(O)R5 steht; R a is halogen, cyano, CC 6 alkyl, C r C 6 alkoxy, haloalkyl CC 6, CC 6 - haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy or C (O) R 5 stands;
R1 Halogen, Cyano, C C6-Alkyl, CrC-e-Halogenalkyl, C2-C6-Alkenyl, C2-C6- Alkinyl, C3-C8-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, C5-C8-Cycloalkenyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, OR6, SR6 oder NR7R8 bedeutet;R 1 halogen, cyano, CC 6 alkyl, CrC-e-haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, optionally with alkyl and / or halogen - or is multiply substituted, C 5 -C 8 cycloalkenyl, which is optionally mono- or polysubstituted with alkyl and / or halogen, is OR 6 , SR 6 or NR 7 R 8 ;
R2 Halogen, Cyano, C C6-Alkyl, C C6-Halogenalkyl, C2-C6-Alkenyl, C2-C6- Alkinyl, C3-C8-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, Cs-Cβ-Cycloalkenyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, OR6, SR6 oder NR7R8 bedeutet;R 2 halogen, cyano, CC 6 alkyl, CC 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, which may be substituted with alkyl and / or halogen or is multiply substituted, Cs-Cβ-cycloalkenyl, which is optionally mono- or polysubstituted by alkyl and / or halogen, is OR 6 , SR 6 or NR 7 R 8 ;
R3 für Wasserstoff, C C6-Alkyl, C C6-Halogenalkyl oder C3-C6-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, steht;R 3 represents hydrogen, CC 6 alkyl, CC 6 haloalkyl or C 3 -C 6 cycloalkyl, which is optionally mono- or polysubstituted by alkyl and / or halogen;
R4 für Wasserstoff, Halogen, Ct-C6-Alkyl, C C6-Halogenalkyl oder C3-C6- Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, steht; R5 Wasserstoff, OH, CrCe-Alkyl, C C6-Alkoxy, C C6-Halogenalkyl, CrC6- Halogenalkoxy, C2-C6-Alkenyl, C C6-Alkylamino oder Di-CrC6-alkylamino, Piperidin-1-yl, Pyrrolidin-1-yl oder Morpholin-4-yl bedeutet;R 4 represents hydrogen, halogen, Ct-C 6 alkyl, CC 6 haloalkyl or C 3 -C 6 cycloalkyl, which is optionally mono- or polysubstituted by alkyl and / or halogen; R 5 is hydrogen, OH, CRCE alkyl, CC 6 alkoxy, CC 6 haloalkyl, -C 6 - haloalkoxy, C 2 -C 6 alkenyl, CC 6 alkylamino or di-CrC 6 alkylamino, piperidin-1-yl , Pyrrolidin-1-yl or morpholin-4-yl;
R6 Wasserstoff, C C6-Alkyl, CrCe-Halogenalkyl, Phenyl-C C -alkyl, worin Phenyl mit Halogen, Alkyl oder Alkoxy ein- oder mehrfach substituiert sein kann, C2-C6-Alkenyl oder COR9 bedeutet;R 6 is hydrogen, CC 6 -alkyl, CrCe-haloalkyl, phenyl-C C -alkyl, where phenyl can be mono- or polysubstituted by halogen, alkyl or alkoxy, is C 2 -C 6 -alkenyl or COR 9 ;
R7, R8 unabhängig voneinander für Wasserstoff, C Cι0-Alkyl, C2-C10-Alkenyl, C4- C10-Alkadienyl, C2-C10-Alkinyl, C3-C8-Cycloalkyl, C5-C8-Cycloalkenyl, C5- C10-Bicycloalkyl, Phenyl, Phenyl-C C4-alkyl, Naphthyl, ein 5- oder 6-gliedriger, gesättigter oder teilweise ungesättigter Heterocyc- lus, der 1, 2 oder 3 Heteroatome, ausgewählt unter N, O und S, als Ringglieder aufweisen kann, oder ein 5- oder 6-gliedriger, aromatischer Heterocyclus, der 1 , 2 oder 3 Hetero- atome, ausgewählt unter N, O und S, als Ringglieder aufweisen kann, wobei die als R7, R8 genannten Reste teilweise oder vollständig halogeniert sein können und/oder 1 , 2 oder 3 Reste Rb aufweisen können, wobei Rb ausgewählt ist unter Cyano, Nitro, OH, d-Cg-Alkyl, C C6-Alkoxy, C C6-Halogenalkyl, C C6-Halogenalkoxy, C C6-AlkyIthio, C2-C6- Alkenyl, C2-C6-Alkenyloxy, C2-C6-Alkinyl, C2-C6-Alkinyloxy, C C6- Alkylamino, Di-C C-e-alkylamino, Piperidin-1-yl, Pyrrolidin-1-yl oder Morpholin-4-yl; R7 mit R8 auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 5-, 6 oder 7-gliedrigen, gesättigten oder ungesättigten Heterocyclus bilden können, der 1 , 2, 3 oder 4 weitere Heteroatome, ausgewählt unter O, S, N und NR10 als Ringglied aufweisen kann, der teilweise oder vollständig halogeniert sein kann und der 1 , 2 oder 3 der Reste Rb aufweisen kann; und R9, R10 unabhängig voneinander Wasserstoff oder CrC6-Alkyl bedeuten; sowie die landwirtschaftlich verträglichen Salze von Verbindungen I.R 7 , R 8 independently of one another for hydrogen, C -C 0 alkyl, C 2 -C 10 alkenyl, C 4 - C 10 alkadienyl, C 2 -C 10 alkynyl, C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, C 5 -C 10 bicycloalkyl, phenyl, phenyl-C C 4 alkyl, naphthyl, a 5- or 6-membered, saturated or partially unsaturated heterocycle, which may have 1, 2 or 3 heteroatoms, selected from N, O and S, as ring members, or a 5- or 6-membered aromatic heterocycle, which Can have 1, 2 or 3 hetero atoms, selected from N, O and S, as ring members, it being possible for the radicals mentioned as R 7 , R 8 to be partially or completely halogenated and / or to have 1, 2 or 3 radicals R b can, wherein R b is selected from cyano, nitro, OH, d-Cg-alkyl, CC 6 -alkoxy, CC 6 -haloalkyl, CC 6 -haloalkoxy, CC 6 -alkyIthio, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyl, C 2 -C 6 -alkynyloxy, CC 6 - alkylamino, di-C Ce-alkylamino, piperidin-1-yl, pyrrolidin-1-yl or morpholin-4- yl; R 7 with R 8 together with the nitrogen atom to which they are attached can also form a 5-, 6 or 7-membered, saturated or unsaturated heterocycle which has 1, 2, 3 or 4 further heteroatoms selected from O, S , N and NR 10 can have as a ring member, which can be partially or completely halogenated and which can have 1, 2 or 3 of the radicals R b ; and R 9 , R 10 are independently hydrogen or C r C 6 alkyl; as well as the agriculturally acceptable salts of compounds I.
Gegenstand der vorliegenden Erfindung ist daher die Verwendung der bicyclischen Verbindungen der allgemeinen Formel I und ihrer landwirtschaftlich verträglichen Salze zur Bekämpfung von pflanzenpathogenen Pilzen (=Schadpilzen) sowie ein Verfahren zur Bekämpfung von pflanzenpathogenen Schadpilzen, das dadurch gekennzeichnet ist, dass man die Pilze, oder die vor Pilzbefall zu schützenden Materialien, Pflanzen, den Boden oder Saatgüter mit einer wirksamen Menge einer Verbindung der allgemeinen Formel I und/oder mit einem landwirtschaftlich verträglichen Salz von I behandelt.The present invention therefore relates to the use of the bicyclic compounds of the general formula I and their agriculturally acceptable salts for combating phytopathogenic fungi (= harmful fungi) and a method for combating phytopathogenic harmful fungi, which is characterized in that the fungi or the Materials, plants, the soil or seeds to be protected from fungal attack are treated with an effective amount of a compound of the general formula I and / or with an agriculturally acceptable salt of I.
Die Verbindungen I sind neu mit Ausnahme der in der US 5,801,183, der WO 96/22990, in J. of Heterocyclic Chemistry, 30, 1993, 909 - 912 und in Chem. Ber. 111, 2813 - 2824 (1978) genannten 1 ,8-Naphthyridine. Dementsprechend betrifft die vorliegende Erfindung auch bicyclische Verbindungen der allgemeinen Formel I und deren landwirtschaftlich verträglichen Salze, ausgenommen: - Verbindungen der allgemeinen Formel I, worin R1 für OH steht, wenn gleichzeitig Y und X jeweils für C-R4 stehen; sowie - 2,4-Dichlor-3-(o-methoxyphenyl)-1 ,8-naphthyridin.The compounds I are new with the exception of those described in US Pat. No. 5,801,183, WO 96/22990, in J. of Heterocyclic Chemistry, 30, 1993, 909-912 and in Chem. Ber. 111, 2813-2824 (1978) called 1,8-naphthyridines. Accordingly, the present invention also relates to bicyclic compounds of the general formula I and their agriculturally acceptable salts, with the exception of: compounds of the general formula I in which R 1 is OH when Y and X are each CR 4 ; and - 2,4-dichloro-3- (o-methoxyphenyl) -1, 8-naphthyridine.
, Gegenstand der vorliegenden Erfindung ist weiterhin ein Mittel zur Bekämpfung von Schadpilzen, enthaltend wenigstens eine Verbindung der allgemeinen Formel I und/oder ein landwirtschaftlich verträgliches Salz davon und wenigstens einen flüssigen oder festen Trägerstoff.The present invention furthermore relates to an agent for combating harmful fungi, comprising at least one compound of the general formula I. and / or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.
Die Verbindungen der Formel I können je nach Substitutionsmuster ein oder mehrere Chiralitätszentren aufweisen und liegen dann als reine Enantiomere oder Diastereome- re oder als Enantiomeren- oder Diastereomerengemische vor. Gegenstand der Erfindung sind sowohl die reinen Enantiomere oder Diastereomere als auch deren Gemische. Gegenstand der Erfindung sind auch Tautomere von Verbindungen der Formel I.Depending on the substitution pattern, the compounds of the formula I can have one or more centers of chirality and are then present as pure enantiomers or diastereomers or as enantiomer or diastereomer mixtures. The invention relates both to the pure enantiomers or diastereomers and to their mixtures. The invention also relates to tautomers of compounds of the formula I.
Unter landwirtschaftlich brauchbaren Salzen kommen vor allem die Salze derjenigen Kationen oder die Säureadditionssalze derjenigen Säuren in Betracht, deren Kationen beziehungsweise Anionen die fungizide Wirkung der Verbindungen I nicht negativ beeinträchtigen. So kommen als Kationen insbesondere die Ionen der Alkalimetalle, vorzugsweise Natrium und Kalium, der Erdalkalimetalle, vorzugsweise Calcium, Magnesi- um und Barium, und der Übergangsmetalle, vorzugsweise Mangan, Kupfer, Zink und Eisen, sowie das Ammoniumion, das gewünschtenfalls ein bis vier Cι-C4-Alkylsubsti- tuenten und/oder einen Phenyl- oder Benzylsubstituenten tragen kann, vorzugsweise Diisopropylammonium, Tetramethylammonium, Tetrabutylammonium, Trimethylbenzyl- ammonium, des weiteren Phosphoniumionen, Sulfoniumionen, vorzugsweise Tri(Cι-C4-alkyl)sulfonium und Sulfoxoniumionen, vorzugsweise Tri(C C4-alkyl)sulf- oxonium, in Betracht.Agriculturally useful salts include, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the fungicidal activity of the compounds I. So come as cations in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which if desired one to four Cι -C 4 alkyl substituents and / or can carry a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 -alkyl) sulfonium and preferably sulfoxonium ions Tri (CC 4 alkyl) sulfoxonium, into consideration.
Anionen von brauchbaren Säureadditionssalzen sind in erster Linie Chlorid, Bromid, Fluorid, Hydrogensulfat, Sulfat, Dihydrogenphosphat, Hydrogenphosphat, Phosphat, Nitrat, Hydrogencarbonat, Carbonat, Hexafluorosilikat, Hexafluorophosphat, Benzoat, sowie die Anionen von CrC^AIkansäuren, vorzugsweise Formiat, Acetat, Propionat und Butyrat. Sie können durch Reaktion von I mit einer Säure des entsprechenden Anions, vorzugsweise der Chlorwasserstoffsäure, Bromwasserstoffsäure, Schwefelsäure, Phosphorsäure oder Salpetersäure, gebildet werden.Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of CrC ^ alkanoic acids, preferably formate and butyrate. They can be formed by reacting I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
Bei den in den vorstehenden Formeln angegebenen Definitionen der Variablen werden Sammelbegriffe verwendet, die allgemein repräsentativ für die jeweiligen Substituenten stehen. Die Bedeutung Cn-Cm gibt die jeweils mögliche Anzahl von Kohlenstoffatomen in dem jeweiligen Substituenten oder Substituententeil an:In the definitions of the variables given in the formulas above, collective terms are used which are generally representative of the respective substituents. The meaning C n -C m indicates the possible number of carbon atoms in the respective substituent or part of the substituent:
Halogen: Fluor, Chlor, Brom und lod;Halogen: fluorine, chlorine, bromine and iodine;
Alkyl sowie alle Alkylteile in Alkoxy, Alkylthio, Alkylamino und Dialkylamino: gesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit 1 bis 4, bis 6, bis 8 oder bis 10 Kohlenstoffatomen, z.B. CrC6-Alkyl wie Methyl, Ethyl, Propyl, 1- Methylethyl, Butyl, 1-Methyl-propyl, 2-Methylpropyl, 1 ,1-Dimethylethyl, Pentyl, 1- Methylbutyl, 2-Methyibutyl, 3-Methylbutyl, 2,2-Di-methylpropyl, 1-Ethylpropyl, Hexyl, 1,1-Dimethylpropyl, 1,2-Dimethylpropyl, 1 -Methyl pentyl, 2-MethyIpentyl, 3- Methylpentyl, 4-Methylpentyl, 1,1-Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Dimethylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1 ,1,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1-Ethyl-1-methyipropyl und 1-Ethyl-2- methylpropyl;Alkyl and all alkyl parts in alkoxy, alkylthio, alkylamino and dialkylamino: saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, to 6, to 8 or to 10 carbon atoms, for example C r C 6 alkyl such as methyl, ethyl, propyl, 1- Methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methyibutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl , 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1,2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methyipropyl and 1-ethyl-2 - methylpropyl;
Halogenalkyl: geradkettige oder verzweigte Alkylgruppen mit 1 bis 4 oder bis 6 Koh- lenstoffatomen (wie vorstehend genannt), wobei in diesen Gruppen teilweise oder vollständig die Wasserstoffatome durch Halogenatome wie vorstehend genannt ersetzt sein können, z.B. Cι-C2-Halogenalkyl wie Chlormethyl, Brommethyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlor- fluormethyl, Chlordifluormethyl, 1-Chlorethyl, 1-Bromethyl, 1-Fluorethyl, 2-Fluorethyl, 2,2-Difluorethyl, 2,2,2-Trifiuorethyl, 2-Chlor-2-fluorethyl, 2-Chlor-2,2-difluorethyl, 2,2- Dichlor-2-fluorethyl, 2,2,2-Trichlorethyl, Pentafluorethyl und 1,1,1-Trifluorprop-2-yl;Haloalkyl: straight-chain or branched alkyl groups with 1 to 4 or to 6 carbon atoms (as mentioned above), it being possible for part or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, Bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl;
Phenyl-Cι-C4-alkyl: für eine durch Phenyl -wie vorstehend genannte - substituierte C C4-Alkylgruppe, z. B. für Benzyl, 1-Phenylethyl, 2-Phenylethyl, 1-Phenylprop-1-yl, 2- Phenylprop-1-yl, 3-Phenylprop-1-yl, 1-Phenylbut-1-yl, 2-Phenylbut-1-yl, 3-Phenylbut-1- yl, 4-PhenyIbut-1-yl, 1-Phenylbut-2-yl, 2-Phenylbut-2-yl, 3-Phenylbut-2-yl, 4-Phenylbut- 2-yl, 1-(Phenylmeth)-eth-1-yl, 1-(Phenylmethyl)-1-(methyl)-eth-1-yl oder - (Phenylmethyl)-1-(methyl)-prop-1-yl; vorzugsweise Benzyl;Phenyl -CC-C 4 alkyl: for a substituted by phenyl - as mentioned above - substituted CC 4 alkyl group, for. B. for benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1 -yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl , 1- (phenylmeth) -eth-1-yl, 1- (phenylmethyl) -1- (methyl) -eth-1-yl or - (phenylmethyl) -1- (methyl) -prop-1-yl; preferably benzyl;
Phenyl-CrC^alkyl, das gegebenenfalls mit Halogen, Alkoxy oder Alkyl ein- oder mehrfach substituiert ist: eine durch Phenyl substituierte CrC -Alkylgruppe, wobei die Phenylgruppe unsubstituiert oder 1 , 2, 3 oder 4, vorzugsweise 1 Substituenten, die ausgewählt sind unter Fluor, Chlor, Brom, d-C6-Alkoxy oder Cι-C6-Alkyl, tragen kann, z. B. für p-Bromphenylmethyl, p-Chlorphenylmethyl, p-Methylphenylmethyl, p- Methylphenylmethyl, p-Methoxyphenylmethyl, p-Methoxyphenylethyl;Phenyl-CrC ^ alkyl, which is optionally mono- or polysubstituted by halogen, alkoxy or alkyl: a phenyl-substituted CrC -alkyl group, the phenyl group being unsubstituted or 1, 2, 3 or 4, preferably 1, substituents selected from Fluorine, chlorine, bromine, dC 6 alkoxy or -CC 6 alkyl, can carry, for. B. for p-bromophenylmethyl, p-chlorophenylmethyl, p-methylphenylmethyl, p-methylphenylmethyl, p-methoxyphenylmethyl, p-methoxyphenylethyl;
Alkenyl: einfach ungesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit 2 bis 4, bis 6 bis 8 oder bis 10 Kohlenstoffatomen und einer Doppelbindung in einer beliebigen Position, z.B. C2-C6-Alkenyl wie Ethenyl, 1-Propenyl, 2-Propenyl, 1- Methylethenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1-Methyl-1-propenyl, 2-Methyl-1- propenyl, 1-Methyl-2-propenyl, 2-Methyl-2-propenyl, 1-Pentenyl, 2-Pentenyl, 3- Pentenyl, 4-Pentenyl, 1-Methyl-1-butenyl, 2-Methyl-1-butenyl, 3-Methyl-1-butenyl, 1- Methyl-2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, 1-Methyl-3-butenyl, 2-Methyl- 3-butenyl, 3-Methyl-3-butenyl, 1 ,1-Dimethyl-2-propenyl, 1 ,2-Dimethyl-1-propenyl, 1,2- Dimethyl-2-propenyl, 1-Ethyl-1propenyl, 1-Ethyl-2-propenyl, 1-Hexenyl, 2-Hexenyl, 3- Hexenyl, 4-Hexenyl, 5-Hexenyl, 1-Methyl-1-pentenyl, 2-Methyl-1-pentenyl, 3-Methyl-1- pentenyl, 4-Methyl-1-pentenyl, 1-Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2- pentenyl, 4-Methyl-2-pentenyl, 1-Methyl-3-pentenyl, 2-Methyl-3pentenyl, 3-Methyl-3- pentenyl, 4-Methyl-3-pentenyl, 1-Methyl-4-pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4- pentenyl, 4-Methyl-4-pentenyl, 1 ,1-Dimethyl-2-butenyl, 1,1-Dimethyl-3-butenyl, 1,2- Dimethyl-1 -butenyl, 1 ,2-Dimethyl-2-butenyl, 1,2-Dimethyl-3-butenyl, 1,3-Dimethyl-1- butenyl, 1 ,3-Dimethyl-2-butenyl, 1,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3- Dimethyl-1 -butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1- butenyl, 3,3-Dimethyl-2-butenyl, 1-Ethyl-1 -butenyl, 1-Ethyl-2-butenyl, 1-Ethyl-3-butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2-Trimethyl-2-propenyl, 1 - Ethyl-l-methyl-2-propenyl, 1-Ethyl-2-methyl-1propenyl und 1-Ethyl-2-methyl-2- propenyl;Alkenyl: monounsaturated, straight-chain or branched hydrocarbon radicals with 2 to 4, to 6 to 8 or to 10 carbon atoms and a double bond in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1 - Methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl , 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2 -butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl -1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3- Hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3pentenyl, 3-methyl-3-pentenyl, 4-methyl- 3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1,1- Dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3 Dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3- Dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1 - ethyl-l-methyl-2-propenyl, 1- Ethyl 2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
Alkadienyl: zweifach ungesättigte, geradkettige oder verzweigte Kohlenwasserstoff- reste mit 4 bis 10 Kohlenstoffatomen und zwei Doppelbindungen in einer beliebigen Position z.B. 1 ,3-Butadienyl, 1-Methyl-1,3-butadienyl, 2-Methyl-1 ,3-butadienyl, Penta- 1,3-dien-1-yl, Hexa-1,4-dien-1-yl, Hexa-1,4-dien-3-yl, Hexa-1 ,4-dien-6-yl, Hexa-1,5- dien-1-yl, Hexa-1 ,5-dien-3-yl, Hexa-1 ,5-dien-4-yl, Hepta-1,4-dien-1-yl, Hepta-1 ,4-dien- 3-yl, Hepta-1,4-dien-6-yl, Hepta-1,4-dien-7-yl, Hepta-1,5-dien-1-yl, Hepta-1,5-dien-3-yl, Hepta-1 ,5-dien-4-yl, Hepta-1 ,5-dien-7-yl, Hepta-1 ,6-dien-1-yl, Hepta-1 ,6-dien-3-yl, Hep- ta-1 ,6-dien-4-yl, Hepta-1,6-dien-5-yl, Hepta-1,6-dien-2-yl, Octa-1 ,4-dien-1-yl, Octa-1,4- dien-2-yl, Octa-1,4-dien-3-yl, Octa-1 ,4-dien-6-yl, Octa-1 ,4-dien-7-yl, Octa-1,5-dien-1-yl, Octa-1,5-dien-3-yl, Octa-1 ,5-dien-4-yl, Octa-1 ,5-dien-7-yl, Octa-1,6-dien-1-yl, Octa-1 ,6- dien-3-yl, Octa-1,6-dien-4-yl, Octa-1 ,6-dien-5-yl, Octa-1,6-dien-2-yl, Deca-1 ,4-dienyl, Deca-1 ,5-dienyl, Deca-1 ,6-dienyl, Deca-1 ,7-dienyl, Deca-1 ,8-dienyl, Deca-2,5-dienyl, Deca-2,6-dienyl, Deca-2,7-dienyl, Deca-2,8-dienyI und dergleichen;Alkadienyl: double-unsaturated, straight-chain or branched hydrocarbon radicals with 4 to 10 carbon atoms and two double bonds in any position, e.g. 1, 3-butadienyl, 1-methyl-1,3-butadienyl, 2-methyl-1, 3-butadienyl, penta-1,3-dien-1-yl, hexa-1,4-dien-1-yl, Hexa-1,4-dien-3-yl, hexa-1, 4-dien-6-yl, hexa-1,5-dien-1-yl, hexa-1, 5-dien-3-yl, hexa- 1, 5-dien-4-yl, hepta-1,4-dien-1-yl, hepta-1, 4-dien-3-yl, hepta-1,4-dien-6-yl, hepta-1, 4-dien-7-yl, hepta-1,5-dien-1-yl, hepta-1,5-dien-3-yl, hepta-1, 5-dien-4-yl, hepta-1, 5- dien-7-yl, Hepta-1, 6-dien-1-yl, Hepta-1, 6-dien-3-yl, Hep-ta-1, 6-dien-4-yl, Hepta-1,6- dien-5-yl, hepta-1,6-dien-2-yl, octa-1, 4-dien-1-yl, octa-1,4-dien-2-yl, octa-1,4-diene 3-yl, octa-1, 4-dien-6-yl, octa-1, 4-dien-7-yl, octa-1,5-dien-1-yl, octa-1,5-dien-3- yl, octa-1,5-dien-4-yl, octa-1,5-dien-7-yl, octa-1,6-dien-1-yl, octa-1,6-dien-3-yl, Octa-1,6-dien-4-yl, Octa-1, 6-dien-5-yl, Octa-1,6-dien-2-yl, Deca-1, 4-dienyl, Deca-1, 5- dienyl, deca-1, 6-dienyl, deca-1, 7-dienyl, deca-1, 8-dienyl, deca-2,5-dienyl, deca-2,6-dienyl, deca-2,7-dienyl, Deca-2,8-dienyI and the like;
Alkinyl: geradkettige oder verzweigte Kohlenwasserstoffgruppen mit 2 bis 4, 2 bis 62 bis 8 oder 2 bis 10 Kohlenstoffatomen und einer Dreifachbindung in einer beliebigen Position, z.B. C2-C6-Alkinyl wie Ethinyl, 1-Propinyl, 2-Propinyl, 1-Butinyl, 2-Butinyl, 3- Butinyl, 1-Methyl-2-propinyl, 1-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1-Methyl-2- butinyl, 1-Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1-butinyl, 1,1-Dimethyl-2- propinyl, 1-Ethyl-2-propinyl, 1-Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1- Methyl-2-pentinyl, 1-Methyl-3-pentinyl, 1-Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2- Methyl-4-pentinyl, 3-Methyl-1-pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1-pentinyl, 4- Methyl-2-pentinyl, 1,1-Dimethyl-2-butinyl, 1,1-Dimethyl-3-butinyl, 1 ,2-Dimethyl-3- butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1-butinyl, 1-Ethyl-2-butinyl, 1-Ethyl-3- butinyl, 2-Ethyl-3-butinyl und 1-Ethyl-1-methyl-2-propinyl; Cycloalkyl: monocyclische, gesättigte Kohlenwasserstoffgruppen mit 3 bis 8, vorzugsweise bis 6 Kohlenstoffringgliedern, wie Cyclopropyl, Cyclobutyl, Cyclopentyl und Cyclohexyl;Alkynyl: straight-chain or branched hydrocarbon groups with 2 to 4, 2 to 62 to 8 or 2 to 10 carbon atoms and a triple bond in any position, for example C 2 -C 6 -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1- Butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1- pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2 Dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; Cycloalkyl: monocyclic, saturated hydrocarbon groups with 3 to 8, preferably up to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
Cycloalkyl, das gegebenenfalls mit Halogen oder Alkyl ein- oder mehrfach substituiert ist: eine - wie vorstehend genannte - unsubstituierte oder 1 , 2, 3 oder 4, vorzugsweise 1 , Substituenten tragende Cycloalkylgruppe, wobei die Substituenten ausgewählt sind unter Fluor, Chlor, Brom oder C C6-Alkyl, z. B. für 4-Chlorcyclohexyl, 4- Bromcyclohexyl, 4-Methylcyclohexyl, 4-Ethylcyclohexyl, 2-ChIorcyclopropyl, 2- Fluorcyclopropyl, 1-Chlorcyclopropyl, 1-Fluorcyclopropyl;Cycloalkyl, which is optionally mono- or polysubstituted by halogen or alkyl: a - as mentioned above - unsubstituted or 1, 2, 3 or 4, preferably 1, substituent-bearing cycloalkyl group, the substituents being selected from fluorine, chlorine, bromine or CC 6 alkyl, e.g. For 4-chlorocyclohexyl, 4-bromocyclohexyl, 4-methylcyclohexyl, 4-ethylcyclohexyl, 2-chlorocyclopropyl, 2-fluorocyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl;
Cycloalkenyl: monocyclische, einfach ungesättigte Kohlenwasserstoffgruppen mit 5 bis 8, vorzugsweise bis 6 Kohlenstoffringgliedern, wie CycIopenten-1-yl, Cyclopenten- 3-yl, Cyclohexen-1-yl, Cyclohexen-3-yl und Cyclohexen-4-yl;Cycloalkenyl: monocyclic, monounsaturated hydrocarbon groups with 5 to 8, preferably up to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl and cyclohexen-4-yl;
Cycloalkenyl, das gegebenenfalls mit Halogen oder Alkyl ein- oder mehrfach substituiert ist: eine - wie vorstehend genannte - unsubstituierte oder 1 , 2, 3 oder 4, vorzugsweise 1 , Substituenten tragende Cycloalkenylgruppe, wobei die Substituenten ausgewählt sind unter Fluor, Chlor, Brom oder C C6-Alkyl, z. B. für 4-Chlorcyclohexen- 1-yl, 4-Bromcyclohexen-1-yl, 4-Methylcyclohexen-1-yl, 4-Ethylcyclohex-1-enyl, 4- Chlorcyclohexen-3-yl, 4-Bromcyclohexen-3-yl, 4-Methylcyclohexen-3-yl, 4- Ethylcyclohex-3-enyl;Cycloalkenyl, which is optionally mono- or polysubstituted by halogen or alkyl: a - as mentioned above - unsubstituted or 1, 2, 3 or 4, preferably 1, substituent-bearing cycloalkenyl group, the substituents being selected from fluorine, chlorine, bromine or CC 6 alkyl, e.g. B. for 4-chlorocyclohexen-1-yl, 4-bromocyclohexen-1-yl, 4-methylcyclohexen-1-yl, 4-ethylcyclohex-1-enyl, 4-chlorocyclohexen-3-yl, 4-bromocyclohexen-3-yl , 4-methylcyclohexen-3-yl, 4-ethylcyclohex-3-enyl;
Bicycloalkyl: bicyclischer Kohlenwasserstoffrest mit 5 bis 10 C-Atomen wie Bicyc- lo[2.2.1]hept-1-yl, Bicyclo[2.2.1]hept-2-yl, Bicyclo[2.2.1]hept-7-yl, Bicyclo[2.2.2]oct-1-yl, Bicyclo[2.2.2]oct-2-yl, Bicyclo[3.3.0]octyl und Bicyclo[4.4.0]decyl.Bicycloalkyl: bicyclic hydrocarbon radical with 5 to 10 carbon atoms, such as bicyclo [2.2.1] hept-1-yl, bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.1] hept-7-yl, Bicyclo [2.2.2] oct-1-yl, bicyclo [2.2.2] oct-2-yl, bicyclo [3.3.0] octyl and bicyclo [4.4.0] decyl.
CrC4-Alkoxy für eine über ein Sauerstoff gebundene Alkylgruppe mit 1 bis 4 C- Atomen: z. B. Methoxy, Ethoxy, n-Propoxy, 1-Methylethoxy, Butoxy, 1-Methylpropoxy, 2-Methylpropoxy oder 1 ,1 -Dimethylethoxy;CrC 4 alkoxy for an oxygen-bonded alkyl group having 1 to 4 carbon atoms: z. B. methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
C-i-Ce-Alkoxy: für C C4-Alkoxy, wie voranstehend genannt, sowie z. B. Pentoxy, 1- Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1,1-Dimethylpropoxy, 1,2- Dimethylpropoxy, 2,2-Dimethylpropoxy, 1-Ethylpropoxy, Hexoxy, 1-Methylpentoxy, 2- Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1 ,1-Dimethylbutoxy, 1 ,2-Ci-Ce alkoxy: for CC 4 alkoxy, as mentioned above, and z. B. pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3- Methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-
Dimethylbutoxy, 1 ,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy, 3,3- Dimethylbutoxy, 1-Ethylbutoxy, 2-Ethylbutoxy, 1 ,1 ,2-Trimethylpropoxy, 1,2,2- Trimethylpropoxy, 1-Ethyl-1-methylpropoxy oder 1-Ethyl-2-methylpropoxy; Cι-C4-Halogenalkoxy: für einen C C -Alkoxyrest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod, vorzugsweise durch Fluor substituiert ist, also z.B. OCH2F, OCHF2) OCF3, OCH2CI, OCHCI2, OCCI3, Chlorfluor- methoxy, Dichlorfluormethoxy, Chlordifluormethoxy, 2-Fluorethoxy, 2-Chlorethoxy, 2-Bromethoxy, 2-lodethoxy, 2,2-Difluorethoxy, 2,2,2-Trifluorethoxy, 2-Chlor-2- fluorethoxy, 2-Chlor-2,2-difluorethoxy, 2,2-Dichlor-2-fluorethoxy, 2,2,2-Trichlorethoxy, OC2F5, 2-Fluorpropoxy, 3-Fluorpropoxy, 2,2-Difluorpropoxy, 2,3-Difluorpropoxy, 2-Chlorpropoxy, 3-Chlorpropoxy, 2,3-Dichlorpropoxy, 2-Brompropoxy, 3-Brompropoxy, 3,3,3-Trifluorpropoxy, 3,3,3-Trichlorpropoxy, OCH2-C2F5l OCF2-C2F5l 1-(CH2F)-2- fluorethoxy, 1-(CH2CI)-2-chlorethoxy, 1-(CH2Br)-2-bromethoxy, 4-Fluorbutoxy, 4- Chlorbutoxy, 4-Brombutoxy oder Nonafluorbutoxy;Dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy; -C-C 4 haloalkoxy: for a CC alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, preferably by fluorine, for example OCH 2 F, OCHF 2) OCF 3 , OCH 2 CI, OCHCI 2 , OCCI 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chlorine -2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC 2 F 5 , 2-fluoropropoxy, 3-fluoropropoxy, 2,2- Difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH 2 -C 2 F 5l OCF 2 -C 2 F 5l 1- (CH 2 F) -2-fluoroethoxy, 1- (CH 2 CI) -2-chloroethoxy, 1- (CH 2 Br) -2-bromethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;
Cι-C6-Halogenalkoxy: für C C4-Halogenalkoxy, wie voranstehend genannt, sowie z.B. 5-Fluorpentoxy, 5-Chlorpentoxy, 5-Brompentoxy, 5-lodpentoxy, Undecafluorpento- xy, 6-Fluorhexoxy, 6-Chlorhexoxy, 6-Bromhexoxy, 6-lodhexoxy oder Dodecafluorhexo- xy;Cι-C 6 haloalkoxy: for CC 4 haloalkoxy, as mentioned above, and for example 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy , 6-iodohexoxy or dodecafluorohexoxy;
Alkenyloxy: Alkenyl wie vorstehend genannt, das über ein Sauerstoffatom gebunden ist, z.B. C2-C6-Alkenyloxy wie Vinyloxy, 1-Propenyloxy, 2-Propenyloxy, 1- Methylethenyloxy, 1-Butenyloxy, 2-Butenyloxy, 3-Butenyloxy, 1-Methyl-1-propeny!oxy, 2-Methyl-1-propenyloxy, 1-Methyl-2-propenyloxy, 2-Methyl-2-propenyloxy, 1- Pentenyloxy, 2-Pentenyloxy, 3-Pentenyloxy, 4-Pentenyloxy, 1-Methyl-1-butenyloxy, 2- Methyl-1 -butenyloxy, 3-Methyl-1-butenyloxy, 1-Methyl-2-butenyloxy, 2-Methyl-2- butenyloxy, 3-Methyl-2-butenyloxy, 1-Methyl-3-butenyloxy, 2-Methyl-3-butenyloxy, 3- Methyl-3-butenyl, 1,1-Dimethyl-2-propenyloxy, 1,2-Dimethyl-1-propenyloxy, 1,2-Alkenyloxy: alkenyl as mentioned above, which is bonded via an oxygen atom, for example C 2 -C 6 alkenyloxy such as vinyloxy, 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1 -Methyl-1-propeny! Oxy, 2-methyl-1-propenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 1-pentenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1 -Methyl-1-butenyloxy, 2-methyl-1-butenyloxy, 3-methyl-1-butenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl -3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyloxy, 1,2-dimethyl-1-propenyloxy, 1,2-
Dimethyl-2-propenyloxy, 1-Ethyl-1propenyloxy, 1-Ethyl-2-propenyloxy, 1-Hexenyloxy, 2-Hexenyloxy, 3-Hexenyloxy, 4-Hexenyloxy, 5-Hexenyloxy, 1-Methyl-1-pentenyloxy, 2- Methyl-1-pentenyloxy, 3-Methyl-1-pentenyloxy, 4-Methyl-1-pentenyloxy, 1-Methyl-2- pentenyloxy, 2-Methyl-2-pentenyloxy, 3-Methyl-2-pentenyloxy, 4-Methyl-2-pentenyloxy, 1-Methyl-3-pentenyloxy, 2-Methyl-3pentenyloxy, 3-Methyl-3-pentenyloxy, 4-Methyl-3- pentenyloxy, 1-Methyl-4-pentenyloxy, 2-Methyl-4-pentenyloxy, 3-Methyl-4-pentenyloxy, 4-Methyl-4-pentenyloxy, 1,1-Dimethyl-2-butenyloxy, 1,1-Dimethyl-3-butenyloxy, 1,2- Dimethyl-1 -butenyloxy, 1 ,2-Dimethyl-2-butenyloxy, 1 ,2-Dimethyl-3-butenyloxy, 1,3- Dimethyl-1 -butenyloxy, 1 ,3-Dimethyl-2-butenyloxy, 1 ,3-Dimethyl-3-butenyloxy, 2,2- Dimethyl-3-butenyloxy, 2,3-Dimethyl-1 -butenyloxy, 2,3-Dimethyl-2-butenyloxy, 2,3- Dimethyl-3-butenyloxy, 3,3-Dimethyl-1 -butenyloxy, 3,3-Dimethyl-2-butenyloxy, 1-Ethyl- 1 -butenyloxy, 1-Ethyl-2-butenyloxy, 1-Ethyl-3-butenyloxy, 2-Ethyl-1 -butenyloxy, 2- Ethyl-2-butenyloxy, 2-Ethyl-3-butenyloxy, 1,1,2-Trimethyl-2-propenyIoxy, 1-Ethyl-1- methyl-2-propenyloxy, 1-Ethyl-2-methyl-1propenyloxy und 1-Ethyl-2-methyl-2- propenyloxy;Dimethyl-2-propenyloxy, 1-ethyl-1-propenyloxy, 1-ethyl-2-propenyloxy, 1-hexenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy, 1-methyl-1-pentenyloxy, 2- Methyl-1-pentenyloxy, 3-methyl-1-pentenyloxy, 4-methyl-1-pentenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy, 3-methyl-2-pentenyloxy, 4-methyl- 2-pentenyloxy, 1-methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy, 1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy, 4-methyl-4-pentenyloxy, 1,1-dimethyl-2-butenyloxy, 1,1-dimethyl-3-butenyloxy, 1,2-dimethyl-1-butenyloxy, 1,2 Dimethyl-2-butenyloxy, 1, 2-dimethyl-3-butenyloxy, 1,3-dimethyl-1-butenyloxy, 1, 3-dimethyl-2-butenyloxy, 1, 3-dimethyl-3-butenyloxy, 2,2- Dimethyl-3-butenyloxy, 2,3-dimethyl-1-butenyloxy, 2,3-dimethyl-2-butenyloxy, 2,3-dimethyl-3-butenyloxy, 3,3-dimethyl-1-butenyloxy, 3,3- Dimethyl-2-butenyloxy, 1-ethyl-1-butenyloxy, 1-ethyl-2-butenyloxy, 1-ethyl-3-butenyloxy, 2-ethyl-1-buteny loxy, 2-ethyl-2-butenyloxy, 2-ethyl-3-butenyloxy, 1,1,2-trimethyl-2-propenyloxy, 1-ethyl-1-methyl-2-propenyloxy, 1-ethyl-2-methyl 1propenyloxy and 1-ethyl-2-methyl-2- propenyloxy;
Alkinyloxy: Alkinyl wie vorstehend genannt, das über ein Sauerstoffatom gebunden ist, z.B. C3-C6-Alkinyloxy wie 2-Propinyloxy, 2-Butinyloxy, 3-Butinyloxy, 1-Methyl-2- propinyloxy, 2-Pentinyloxy, 3-Pentinyloxy, 4-Pentinyloxy, 1-Methyl-2-butinyloxy, 1- Methyl-3-butinyloxy, 2-Methyl-3-butinyloxy, 1-Ethyl-2-propinyloxy, 2-Hexinyloxy, 3- Hexinyloxy, 4-Hexinyloxy, 5-Hexinyloxy, 1-Methyl-2-pentinyloxy, 1-Methyl-3-pentinyloxy und dergleichen;Alkynyloxy: alkynyl as mentioned above which is bonded via an oxygen atom, for example C 3 -C 6 -alkynyloxy such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy , 4-pentynyloxy, 1-methyl-2-butynyloxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy, 5 -Hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl-3-pentynyloxy and the like;
fünf- oder sechsgliedriger gesättigtes oder partiell ungesättigter Heterocyclus, enthaltend ein, zwei oder drei Heteroatome aus der Gruppe Sauerstoff, Stickstoff und Schwefel: z.B. mono- und bicyclische Heterocyclen (Heterocyclyl) enthaltend neben Kohlenstoffringgliedern ein bis drei Stickstoffatome und/oder ein Sauerstoff- oder Schwefelatom oder ein oder zwei Sauerstoff- und/oder Schwefelatome, z.B. 2- Tetrahydrofuranyl, 3-Tetrahydrofuranyl, 2-Tetrahydrothienyl, 3-Tetrahydrothienyl, 2- Pyrrolidinyl, 3-Pyrrolidinyl, 3-lsoxazolidinyl, 4-lsoxazolidinyl, 5-lsoxazolidinyl, 3- Isothiazolidinyl, 4-lsothiazolidinyl, 5-lsothiazolidinyl, 3-Pyrazolidinyl, 4-Pyrazolidinyl, 5- Pyrazolidinyl, 2-Oxazolidinyl, 4-Oxazolidinyl, 5-Oxazolidinyl, 2-Thiazolidinyl, 4- Thiazolidinyl, 5-Thiazolidinyl, 2-lmidazolidinyl, 4-lmidazolidinyl, 1,2,4-Oxadiazolidin-3- yl, 1 ,2,4-Oxadiazolidin-5-yl, 1 ,2,4-Thiadiazolidin-3-yl, 1,2,4-Thiadiazolidin-5-yl, 1,2,4- Triazolidin-3-yl, 1 ,3,4-Oxadiazolidin-2-yl, 1 ,3,4-Thiadiazolidin-2-yl, 1 ,3,4-Triazolidin-2-yl, 2,3-Dihydrofur-2-yl, 2,3-Dihydrofur-3-yl, 2,4-Dihydrofur-2-yl, 2,4-Dihydrofur-3-yl, 2,3- Dihydrothien-2-yl, 2,3-Dihydrothien-3-yl, 2,4-Dihydrothien-2-yl, 2,4-Dihydrothien-3-yl, 2- Pyrrolin-2-yl, 2-Pyrrolin-3-yl, 3-Pyrrolin-2-yl, 3-Pyrrolin-3-yl, 2-lsoxazolin-3-yl, 3- lsoxazolin-3-yl, 4-lsoxazolin-3-yl, 2-lsoxazolin-4-yl, 3-lsoxazolin-4-yl, 4-lsoxazolin-4-yl, 2-lsoxazolin-5-yl, 3-lsoxazolin-5-yl, 4-lsoxazolin-5-yl, 2-lsothiazolin-3-yl, 3-lsothiazolin- 3-yl, 4-lsothiazolin-3-yl, 2-lsothiazolin-4-yl, 3-lsothiazolin-4-yl, 4-lsothiazolin-4-yl, 2- lsothiazolin-5-yl, 3-lsothiazolin-5-yl, 4-lsothiazolin-5-yl, 2,3-Dihydropyra∑ol-l-yl, 2,3- Dihydropyrazol-2-yl, 2,3-Dihydropyrazol-3-yl, 2,3-Dihydropyrazol-4-yl, 2,3- Dihydropyrazol-5-yl, 3,4-Dihydropyrazol-1-yl, 3,4-Dihydropyrazol-3-yl, 3,4- Dihydropyrazol-4-yl, 3,4-Dihydropyrazol-5-yl, 4,5-Dihydropyrazol-1-yl, 4,5- Dihydropyrazol-3-yl, 4,5-Dihydropyrazol-4-yl, 4,5-Dihydropyrazol-5-yl, 2,3- Dihydrooxazol-2-yl, 2,3-Dihydrooxazol-3-yl, 2,3-Dihydrooxazol-4-yl, 2,3-Dihydrooxazol- 5-yl, 3,4-Dihydrooxazol-2-yl, 3,4-Dihydrooxazol-3-yl, 3,4-Dihydrooxazol-4-yl, 3,4- Dihydrooxazol-5-yl, 3,4-Dihydrooxazol-2-yl, 3,4-Dihydrooxazol-3-yl, 3,4-Dihydrooxazol- 4-yl, 2-Piperidinyl, 3-Piperidinyl, 4-Piperidinyl, 1,3-Dioxan-5-yl, 2-Tetrahydropyranyl, 4-Tetrahydropyranyl, 2-Tetrahydrothienyl, 3-Hexahydropyridazinyl, 4- Hexahydropyridazinyl, 2-Hexahydropyrimidinyl, 4-Hexahydropyrimidinyl, 5- Hexahydropyrimidinyl, 2-Piperazinyl, 1,3,5-Hexahydro-triazin-2-yl und 1,2,4- H exa hyd rotriazi n-3-y l ;five- or six-membered saturated or partially unsaturated heterocycle, containing one, two or three heteroatoms from the group consisting of oxygen, nitrogen and sulfur: for example mono- and bicyclic heterocycles (heterocyclyl) containing, in addition to carbon ring members, one to three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl Isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5- yl, 1,2,4-triazolidin-3-yl, 1, 3,4-oxadiazolidin-2-yl, 1, 3,4-thiadiaz olidin-2-yl, 1, 3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2, 4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2- Pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin 3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5- yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2- isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyra∑ol-l-yl, 2,3-dihydropyrazol-2-yl, 2,3- Dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4- Dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5- Dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-y l, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3- yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrim Hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydro-triazin-2-yl and 1,2,4- H exa hyd rotriazi n-3-yl;
fünf- bis sechsgliedriger aromatischer Heterocyclus, enthaltend ein, zwei oder drei Heteroatome aus der Gruppe Sauerstoff, Stickstoff oder Schwefel: ein- oder zweikerniges Heteroaryl, z.B. C-gebundenes 5-gliedriges Heteroaryl, enthaltend ein bis drei Stickstoffatome oder ein oder zwei Stickstoffatome und ein Schwefel- oder Sauerstoffatom als Ringglieder wie 2-Furyl, 3-Furyl, 2-Thienyl, 3-Thienyl, 2-Pyrrolyl, 3- Pyrrolyl, 3-lsoxazolyl, 4-lsoxazolyl, 5-lsoxazolyl, 3-lsothiazolyl, 4-lsothiazolyl, 5- Isothiazolyl, 3-Pyrazolyl, 4-Pyrazolyl, 5-Pyrazolyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Thiazolyl, 4-Thiazolyl, 5-Thiazolyl, 2-lmidazolyl, 4-lmidazolyl, 1 ,2,4-Oxadiazol-3-yl, 1,2,4-Oxadiazol-5-yl, 1 ,2,4-Thiadiazol-3-yl, 1,2,4-Thiadiazol-5-yl, 1,2,4-Triazol-3-yl, 1 ,3,4-Oxadiazol-2-yl, 1 ,3,4-Thiadiazol-2-yl und 1,3,4-Triazol-2-yl; über Stickstoff gebundenes 5-gliedriges Heteroaryl, enthaltend ein bis drei Stickstoffatome als Ringglieder wie Pyrrol-1-yl, Pyrazol-1-yl, lmidazol-1-yl, 1,2,3-Triazol-1-yl und 1,2,4-Triazol-1-yl; 6-gliedriges Heteroaryl, enthaltend ein bis drei Stickstoffatome ein bis drei Stickstoffatome als Ringglieder wie Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, 3-Pyridazinyl, 4- Pyridazinyl, 2-Pyrimidinyl, 4-Pyrimidinyl, 5-Pyrimidinyl, 2-Pyrazinyl, 1,3,5-Triazin-2-yl und 1 ,2,4-Triazin-3-yl.five- to six-membered aromatic heterocycle containing one, two or three heteroatoms from the group consisting of oxygen, nitrogen or sulfur: mononuclear or dinuclear heteroaryl, e.g. C-linked 5-membered heteroaryl, containing one to three nitrogen atoms or one or two nitrogen atoms and a sulfur or oxygen atom as ring members such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl , 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2 -Thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1, 2,4-thiadiazole -3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1, 3,4-oxadiazol-2-yl, 1, 3,4-thiadiazol-2 -yl and 1,3,4-triazol-2-yl; 5-membered heteroaryl bonded via nitrogen and containing one to three nitrogen atoms as ring members such as pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,3-triazol-1-yl and 1,2, 4-triazol-1-yl; 6-membered heteroaryl containing one to three nitrogen atoms and one to three nitrogen atoms as ring members such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl , 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1, 2,4-triazin-3-yl.
Eine erste bevorzugte Ausführungsform der vorliegenden Erfindung betrifft Verbindungen der Formel I, worin X und Y jeweils für C-R4steht, wobei R4 jeweils gleich oder verschieden sein können. Diese Verbindungen werden im Folgenden als Verbindungen a bezeichnet.A first preferred embodiment of the present invention relates to compounds of the formula I in which X and Y each represent CR 4 , where R 4 can each be the same or different. These compounds are referred to below as compounds a.
Eine weitere bevorzugte Ausführungsform der vorliegenden Erfindung betrifft Verbindungen der Formel I, worin X für C-R4 steht und Y für N steht. Diese Verbindungen werden im Folgenden als Verbindungen l.b bezeichnet.Another preferred embodiment of the present invention relates to compounds of the formula I in which X is CR 4 and Y is N. These connections are referred to below as connections 1b.
Eine weitere bevorzugte Ausführungsform der vorliegenden Erfindung betrifft Verbindungen der Formel I, worin X für N steht und Y für C-R4 steht. Diese Verbindungen werden im Folgenden als Verbindungen l.c bezeichnet. Another preferred embodiment of the present invention relates to compounds of the formula I in which X is N and Y is CR 4 . These connections are referred to below as connections lc.
In den Formeln der Formel La, l.b ind l.c haben die Variablen Ra, n, R1, R2, R3 und R4 die zuvor genannten Bedeutungen, insbesondere die im Folgenden als bevorzugt an- gegebenen Bedeutungen.In the formulas of the formula Ia, Ib and Ic, the variables R a , n, R 1 , R 2 , R 3 and R 4 have the meanings mentioned above, in particular the meanings given below as preferred.
Im Hinblick auf die Verwendung der erfindungsgemäßen Verbindungen I als Fungizide weisen die Variablen n, Ra, R1, R2, R3 und R4 unabhängig voneinander und vorzugsweise in Kombination die folgenden Bedeutungen auf:With regard to the use of the compounds I according to the invention as fungicides, the variables n, R a , R 1 , R 2 , R 3 and R 4 have the following meanings independently of one another and preferably in combination:
n 2, 3, 4 oder 5, insbesondere 2 oder 3;n 2, 3, 4 or 5, in particular 2 or 3;
Ra Halogen, insbesondere Fluor oder Chlor, CrC4-Alkyl, insbesondere Methyl, C C4-Alkoxy, insbesondere Methoxy, CrC2-Fluoralkyl, insbesondere Difluormethyl und Trifluormethyl, CrC2-Fluoralkoxy, insbesondere Difluormethoxy und Trifluor- methoxy, CrC4-Alkoxycarbonyl, insbesondere Methoxycarbonyl und Cyano;. Besonders bevorzugt ist Ra ausgewählt unter Halogen, speziell Fluor oder Chlor, CrC4-Alkyl, speziell Methyl, und C C -Alkoxy, speziell Methoxy;R a halogen, in particular fluorine or chlorine, CrC 4 -alkyl, in particular methyl, CC 4 -alkoxy, in particular methoxy, CrC 2 -fluoroalkyl, in particular difluoromethyl and trifluoromethyl, CrC 2 -fluoroalkoxy, in particular difluoromethoxy and trifluoromethoxy, CrC 4 - Alkoxycarbonyl, especially methoxycarbonyl and cyano ;. R a is particularly preferably selected from halogen, especially fluorine or chlorine, CrC 4 alkyl, especially methyl, and CC alkoxy, especially methoxy;
R1 Halogen, speziell Chlor, Hydroxy oder eine Gruppe NR7R8;R 1 halogen, especially chlorine, hydroxy or a group NR 7 R 8 ;
R2 Halogen, speziell Chlor, Hydroxy, CrC6-Alkyl, speziell Methyl; CrC6 Halogenalkyl oder eine Gruppe NR'R ;R 2 halogen, especially chlorine, hydroxy, CrC 6 alkyl, especially methyl; CrC 6 haloalkyl or a group NR'R;
R3 Wasserstoff, CrCe-Alkyl, vorzugsweise CrC3-Alkyl, CrCe-Halogenalkyl, vorzugsweise CrC3-Halogenalkyl, und besonders bevorzugt Wasserstoff;R 3 is hydrogen, CrCe-alkyl, preferably CrC 3 -alkyl, CrCe-haloalkyl, preferably CrC 3 -haloalkyl, and particularly preferably hydrogen;
R4 Wasserstoff, Halogen, C C6-Alkyl, vorzugsweise CrC3-Alkyl, CrCe- Halogenalkyl, vorzugsweise CrC3-Halogenalkyl, und besonders bevorzugt Wasserstoff. Sofern R1 für Halogen, speziell Chlor steht, bedeutet R2 vorzugsweise Halogen, speziell Chlor, CrCe-Alkyl, speziell Methyl, CrC6-Halogenalkyl oder eine Gruppe NR7R8.R 4 is hydrogen, halogen, CC 6 alkyl, preferably CrC 3 alkyl, CrCe haloalkyl, preferably CrC 3 haloalkyl, and particularly preferably hydrogen. If R 1 is halogen, especially chlorine, R 2 is preferably halogen, especially chlorine, CrCe-alkyl, especially methyl, CrC 6 -haloalkyl or a group NR 7 R 8 .
Sofern R1 für Hydroxy steht, bedeutet R2 vorzugsweise Hydroxy, C C6-Alkyl oder C Ce-Halogenalkyl.If R 1 is hydroxy, R 2 is preferably hydroxy, CC 6 alkyl or C Ce-haloalkyl.
Sofern R1 für eine Gruppe NR7R8 steht, ist R2 vorzugsweise ausgewählt unter Halogen, speziell Chlor, C C6-Alkyl, speziell Methyl und CrC6-Halogenalkyl.If R 1 represents a group NR 7 R 8, R 2 is preferably selected from halogen, especially chlorine, CC 6 alkyl, especially methyl, and -C 6 haloalkyl.
Sofern R1 für eine Gruppe NR7R8 steht, ist vorzugsweise wenigstens einer der Reste R7, R8 von Wasserstoff verschieden. Insbesondere steht R7 für CrC6-Alkyl. C3-C8- Cycloalkyl, das gegebenenfalls mit Alkyl ein- oder mehrfach substituiert ist, CrCe- Halogenalkyl, Phenyl-CrC4-alkyl, C2-C6-Alkenyl oder C2-C6-Alkinyl. R8 steht insbeson- dere für Wasserstoff, CrC6-Alkyl oder C2-C6-Alkenyl und ganz besonders bevorzugt für Wasserstoff und C C4-Alkyl.If R 1 is a group NR 7 R 8 , at least one of the radicals R 7 , R 8 is preferably different from hydrogen. In particular, R 7 represents CrC 6 alkyl. C 3 -C 8 cycloalkyl, which is optionally mono- or polysubstituted with alkyl, CrCe-haloalkyl, phenyl-CrC 4 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl. R 8 stands in particular for hydrogen, CrC 6 alkyl or C 2 -C 6 alkenyl and very particularly preferably for hydrogen and CC 4 alkyl.
Zu den bevorzugten Gruppen NR7R8 zählen auch solche, die für einen gesättigten oder teilweise ungesättigten heterocyclischen Rest stehen, der neben dem Stickstoffatom ein weiteres Heteroatom, ausgewählt unter O, S, und NR10 als Ringglied aufweisen kann, und der ein oder zwei Substituenten aufweisen kann, die ausgewählt sind unter Halogen, Hydroxy, CrC6-Alkyl und C C6-Halogenalkyl. Vorzugsweise weist der hete- rocyclische Rest 5 bis 7 Atome als Ringglieder auf. Beispiele für derartige heterocycli- sche Reste sind Pyrrolidin, Piperidin, Morpholin, Tetrahydropyridin, z.B. 1 ,2,3,6 Tetra- hydropyridin, Piperazin und Azepan, die in der vorgenannten Weise substituiert sein können.The preferred groups NR 7 R 8 also include those which represent a saturated or partially unsaturated heterocyclic radical which, in addition to the nitrogen atom, can have a further heteroatom selected from O, S and NR 10 as a ring member, and one or two May have substituents which are selected from halogen, hydroxy, CrC 6 alkyl and CC 6 haloalkyl. The heterocyclic radical preferably has 5 to 7 atoms as ring members. Examples of such heterocyclic radicals are pyrrolidine, piperidine, morpholine, tetrahydropyridine, for example 1, 2,3,6 tetrahydropyridine, piperazine and azepane, which can be substituted in the aforementioned manner.
Sofern R2 für eine Gruppe NR7R8 steht, ist vorzugsweise wenigstens einer der Reste R7, R8 von Wasserstoff verschieden. Insbesondere weist R7 die zuvor als bevorzugt genannten Bedeutungen auf.If R 2 represents a group NR 7 R 8 , at least one of the radicals R 7 , R 8 is preferably different from hydrogen. In particular, R 7 has the meanings previously mentioned as preferred.
Bevorzugte Bedeutungen von Ra umfassen Halogen, speziell F oder Cl, Trifluormethyl,Preferred meanings of R a include halogen, especially F or Cl, trifluoromethyl,
CN, CrC4-Alkoxy, C C -Alkoxycarbonyl, insbesondere Methoxycarbonyl.CN, CrC 4 alkoxy, CC alkoxycarbonyl, especially methoxycarbonyl.
Im Hinblick auf die Verwendung der erfindungsgemäßen Verbindungen I als FungizideWith regard to the use of the compounds I according to the invention as fungicides
steht der Rest vorzugsweise für einen Rest der Formel the rest is preferably a radical of the formula
worin Ra1 die zuvor für Ra genannten Bedeutungen aufweist und die Reste Ra2, Ra3, Ra4 und Ra5 die für Ra angegebenen Bedeutungen haben oder für Wasserstoff stehen. Ins- besondere stehen:in which R a1 has the meanings given above for R a and the radicals R a2 , R a3 , R a4 and R a5 have the meanings indicated for R a or are hydrogen. In particular:
Ra1 für Fluor, Chlor, Trifluormethyl oder Methyl;R a1 for fluorine, chlorine, trifluoromethyl or methyl;
Ra2 für Wasserstoff oder Fluor;R a2 for hydrogen or fluorine;
Ra3 für Wasserstoff, Fluor, Chlor, Cyano, C1-C4-Alkyl, speziell Methyl, C C -Alkoxy, speziell Methoxy oder C C4-Alkoxycarbonyl, speziell Methoxycarbonyl; Ra4 für Wasserstoff, Chlor oder Fluor;R a3 for hydrogen, fluorine, chlorine, cyano, C 1 -C 4 alkyl, especially methyl, CC alkoxy, especially methoxy or CC 4 alkoxycarbonyl, especially methoxycarbonyl; R a4 for hydrogen, chlorine or fluorine;
Ra5 für Wasserstoff, Fluor, Chlor oder C C4-Alkyl, speziell Methyl, oder CrC4-Alkoxy, speziell Methoxy.R a5 for hydrogen, fluorine, chlorine or CC 4 -alkyl, especially methyl, or CrC 4 -alkoxy, especially methoxy.
Hierbei ist vorzugsweise wenigstens einer der Reste Ra3 oder Ra5 von Wasserstoff ver- schieden. Vorzugsweise steht wenigstens einer und besonders bevorzugt beide Reste Ra2, Ra4 für Wasserstoff.Here, at least one of the radicals R a3 or R a5 is preferably different from hydrogen. Preferably at least one and particularly preferably both radicals R a2 , R a4 are hydrogen.
Eine bevorzugte Ausführungsform der erfindungsgemäßen Verbindungen l.b sind solche, worin R2 für Halogen, Cyano, CrC6-Alkyl, CrC6-HalogenaIkyl, C2-C6-Alkenyl, C2- C6-AlkinyL C3-C8-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, C5-C8-Cycloalkenyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, oder NR7R8 steht, worin R7 und R8 jeweils von Wasserstoff verschieden sind.A preferred embodiment of the compounds of the invention are those wherein R 2 is halo, cyano, -C 6 alkyl, CrC 6 -HalogenaIkyl, C 2 -C 6 alkenyl, C 2 lb - C 6 alkynyl C 3 -C 8 cycloalkyl , which is optionally mono- or polysubstituted with alkyl and / or halogen, C 5 -C 8 cycloalkenyl which is optionally monosubstituted or polysubstituted with alkyl and / or halogen, or NR 7 R 8 , in which R 7 and R 8 are each different from hydrogen.
Eine andere bevorzugte Ausführungsform der erfindungsgemäßen Verbindungen La und l.c betrifft solche, worin R2 Halogen, Cyano, CrC6-Alkyl, CrC6-Halogenalkyl, C2- Ce-Alkenyl, C2-C6-Alkinyl, C3-C8-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, C5-C8-Cycloalkenyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, OR6, SR6 oder NR7R8 be- deutet, worin R6, R7 und R8 die zuvor genannten und insbesondere die bevorzugten Bedeutungen aufweisen.Another preferred embodiment of the compounds according to the invention La and lc relates to those, wherein R 2 is halogen, cyano, -C 6 alkyl, -C 6 haloalkyl, C 2 - Ce alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 -Cycloalkyl, which is optionally mono- or polysubstituted with alkyl and / or halogen, C 5 -C 8 -cycloalkenyl, which is mono- or polysubstituted or substituted with alkyl and / or halogen, OR 6 , SR 6 or NR 7 R 8 means in which R 6 , R 7 and R 8 have the abovementioned and in particular the preferred meanings.
Im Übrigen weisen die Variablen R3, R4, R5 und R6 unabhängig voneinander und vorzugsweise in Kombination mit den bevorzugten Bedeutungen der Variablen n, Ra, R1 und R2 die folgenden Bedeutungen auf: R3 Wasserstoff, CrC6-Alkyl, vorzugsweise CrC3-Alkyl, CrC6-Halogenalkyl, vorzugsweise CrC3-Halogenalkyl, und besonders bevorzugt Wasserstoff; R4 Wasserstoff, C C6-Alkyl, vorzugsweise C C3-Alkyl, CrC6-Halogenalkyl, vor- zugsweise CrC3-Halogenalkyl, und besonders bevorzugt Wasserstoff;Otherwise, the variables R 3 , R 4 , R 5 and R 6 are independent of one another and preferably in combination with the preferred meanings of the variables n, R a , R 1 and R 2 have the following meanings: R 3 is hydrogen, -C 6 alkyl, preferably -C 3 alkyl, -C 6 haloalkyl, preferably -C 3 haloalkyl, and particularly preferably hydrogen; R 4 is hydrogen, CC 6 alkyl, preferably CC 3 alkyl, -C 6 haloalkyl, preferably -C 3 haloalkyl, and particularly preferably hydrogen;
R5 Wasserstoff, C C4-Alkyl oder C C4-Alkoxy; R6 Wasserstoff, C C4-Alkyl, Benzyl oder C C4-Alkylcarbonyl.R 5 is hydrogen, CC 4 alkyl or CC 4 alkoxy; R 6 is hydrogen, CC 4 alkyl, benzyl or CC 4 alkyl carbonyl.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2-Methyl-4-chlor steht (Verbindungen l.a.1, l.b.l.und l.c.1). Beispiele hierfür sind Verbindungen l.a.1, l.b.l.und l.c.1, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.1, l.b.l.und l.c.1, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.1, l.b.l.und l.c.1, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.1, l.b.l.und l.c.1, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.1, l.b.l.und l.c.1, worin R2 Me- thyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to use as a fungicide are the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2-methyl-4-chlorine (compounds la1, lblund lc1). Examples of these are compounds la1, lblund lc1, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds la1, lblund lc1, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds la1, lblund lc1, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds la1, lblund lc1, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la1, lblund lc1, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Tabelle A:Table A:
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2-Fluor-4-methyl steht (Verbindungen l.a.2, l.b.2 und l.c.2). Beispiele hierfür sind Verbindungen l.a.2, l.b.2 und l.c.2, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.2, l.b.2 und l.c.2, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.2, l.b.2 und l.c.2, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.2, l.b.2 und l.c.2, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.2, l.b.2 und l.c.2, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-fluoro-4-methyl (compounds la2, lb2 and lc2). Examples include compounds LA2, LB2 and LC2, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds la2, lb2 and lc2, in which R 2 and R 1 are each chlorine. Examples of these are also compounds la2, lb2 and lc2, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds la2, lb2 and lc2, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la2, lb2 and lc2, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,6-Dimethyl steht (Verbindungen l.a.3, l.b.3 und l.c.3). Beispiele hierfür sind Verbindungen l.a.3, l.b.3 und l.c.3, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.3, l.b.3 und l.c.3, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.3, l.b.3 und l.c.3, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.3, l.b.3 und l.c.3, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeu- tungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.3, l.b.3 und l.c.3, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,6-dimethyl (compounds la3, lb3 and lc3). Examples of these are compounds la3, lb3 and lc3, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds la3, lb3 and lc3, in which R 2 and R 1 are each chlorine. Examples of these are also compounds la3, lb3 and lc3, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds la3, lb3 and lc3, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la3, lb3 and lc3, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,4,6-Trimethyl steht (Verbindungen l.a.4, l.b.4 und l.c.4). Beispiele hierfür sind Verbindungen l.a.4, l.b.4 und l.c.4, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.4, l.b.4 und l.c.4, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.4, l.b.4 und l.c.4, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.4, l.b.4 und l.c.4, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.4, l.b.4 und l.c.4, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,4,6-trimethyl (compounds la4, lb4 and lc4). Examples of these are compounds la4, lb4 and lc4, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds la4, lb4 and lc4, in which R 2 and R 1 are each chlorine. Examples of these are also compounds la4, lb4 and lc4, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA4, LB4 and LC4, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together have the meanings given in one row of Table A. Examples of these are also compounds la4, lb4 and lc4, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,6-Difluor-4-methyl steht (Verbindungen l.a.5, l.b.5 und l.c.5). Beispiele hierfür sind Verbindungen l.a.5, l.b.5 und l.c.5, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.5, l.b.5 und l.c.5, wor- in R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.5, l.b.5 und l.c.5, worin R2 Methyl bedeutet und R Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.5, l.b.5 und l.c.5, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.5, l.b.5 und l.c.5, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2,6-difluoro-4-methyl (compounds la5, lb5 and lc5). Examples include compounds LA5, LB5 and LC5, in which R 2 and R 1 each represent hydroxy. Examples of this are also compounds LA5, LB5 and LC5, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds la5, lb5 and lc5, in which R 2 is methyl and R is chlorine. Examples of these are also compounds la5, lb5 and lc5, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA5, LB5 and LC5, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,6-Difluor-4-cyano steht (Verbindungen l.a.6, l.b.6 und l.c.6). Beispiele hierfür sind Verbindungen l.a.6, l.b.6 und l.c.6, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.6, l.b.6 und l.c.6, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.6, l.b.6 und l.c.6, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.6, l.b.6 und l.c.6, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.6, l.b.6 und l.c.6, worin R2 Methyl bedeutet und R für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,6-difluoro-4-cyano (compounds la6, lb6 and lc6). Examples include compounds LA6, LB6 and LC6, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA6, LB6 and LC6, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds la6, lb6 and lc6, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds la6, lb6 and lc6, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA6, LB6 and LC6, in which R 2 is methyl and R is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,6-Difluor-4-methoxycarbonyl steht (Verbindungen l.a.7, l.b.7 und l.c.7). Beispiele hierfür sind Verbindungen l.a.7, l.b.7 und Lc.7, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.7, l.b.7 und l.c.7, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.7, l.b.7 und l.c.7, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.7, l.b.7 und l.c.7, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.7, l.b.7 und l.c.7, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2,6-difluoro-4-methoxycarbonyl (compounds la7, lb7 and lc7). Examples of these are compounds LA7, LB7 and LC7, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA7, LB7 and LC7, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds la7, lb7 and lc7, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds la7, lb7 and lc7, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA7, LB7 and LC7, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel a, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2-Trifluormethyl-4-fluor steht (Verbindungen l.a.8, l.b.8 und l.c.8). Beispiele hierfür sind Verbindungen l.a.8, l.b.8 und l.c.8, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.8, l.b.8 und l.c.8, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.8, l.b.8 und l.c.8, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.8, l.b.8 und l.c.8, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.8, l.b.8 und l.c.8, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicide are also the compounds of the general formulas a, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-trifluoromethyl-4-fluorine (compounds la8, lb8 and lc8). Examples of these are compounds LA8, LB8 and LC8, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA8, LB8 and LC8, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA8, LB8 and LC8, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA8, LB8 and LC8, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA8, LB8 and LC8, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2-Trifluormethyl-5-fluor steht (Verbindungen l.a.9, l.b.9 und l.c.9). Beispiele hierfür sind Verbindungen l.a.9, l.b.9 und l.c.9, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.9, l.b.9 und l.c.9, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.9, l.b.9 und l.c.9, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.9, l.b.9 und l.c.9, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.9, l.b.9 und l.c.9, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-trifluoromethyl-5-fluorine (compounds la9, lb9 and lc9). Examples include compounds LA9, LB9 and LC9, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA9, LB9 and LC9, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA9, LB9 and LC9, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds la9, lb9 and lc9, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la9, lb9 and lc9, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2-Trifluormethyl-5-chlor steht (Verbindungen l.a.10, l.b.10 und l.c.10). Beispiele hierfür sind Verbindungen l.a.10, l.b.10 und l.c.10, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.10, l.b.10 und l.c.10, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbin- düngen l.a.10, l.b.10 und l.c.10, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.10, l.b.10 und l.c.10, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.10, l.b.10 und l.c.10, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n represents 2-trifluoromethyl-5-chlorine (compounds LA10, LB10 and LC10). Examples of these are compounds LA10, LB10 and LC10, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA10, LB10 and LC10, in which R 2 and R 1 each represent chlorine. Examples of this are also fertilize la10, lb10 and lc10, where R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA10, LB10 and LC10, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA10, LB10 and LC10, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2-Chlor-6-fluor steht (Verbindungen l.a.11, l.b.11 und l.c.11). Beispiele hierfür sind Verbindungen l.a.11 , l.b.11 und l.c.11 , worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.11, l.b.11 und l.c.11, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.11, l.b.11 und l.c.11, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.11, l.b.11 und l.c.11 , worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.11 , l.b.11 und l.c.11 , worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-chloro-6-fluorine (compounds la11, lb11 and lc11). Examples include compounds LA11, LB11 and LC11, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA11, LB11 and LC11, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds la11, lb11 and lc11, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds la11, lb11 and lc11, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la11, lb11 and lc11, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,6-Difluor steht (Verbindungen l.a.12, Lb.12 und l.c.12). Beispiele hierfür sind Verbindungen l.a.12, Lb.12 und l.c.12, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.12, Lb.12 und l.c.12, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.12, Lb.12 und l.c.12, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.12, Lb.12 und l.c.12, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.12, Lb.12 und l.c.12, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,6-difluoro (compounds la12, Lb.12 and lc12). Examples include compounds LA12, Lb.12 and LC12, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA12, Lb.12 and LC12, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA12, Lb.12 and LC12, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA12, Lb.12 and LC12, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA12, Lb.12 and LC12, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,6-Dichlor steht (Verbindungen l.a.13, l.b.13 und l.c.13). Beispiele hierfür sind Verbindungen l.a.13, l.b.13 und l.c.13, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.13, l.b.13 und l.c.13, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.13, l.b.13 und l.c.13, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.13, l.b.13 und l.c.13, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.13, l.b.13 und l.c.13, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as a fungicide are also the compounds of the general formula La, Ib and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxy, chlorine or methyl and (R a ) n is 2,6-dichloro (compounds la13, lb13 and lc13). Examples include compounds LA13, LB13 and LC13, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA13, LB13 and LC13, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA13, LB13 and LC13, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA13, LB13 and LC13, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA13, LB13 and LC13, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2-Fluor-6-methyl steht (Verbindungen l.a.14, l.b.14 und l.c.14). Beispiele hierfür sind Verbindungen l.a.14, l.b.14 und l.c.14, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.14, l.b.14 und l.c.14, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.14, l.b.14 und l.c.14, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.14, l.b.14 und l.c.14, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.14, l.b.14 und l.c.14, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-fluoro-6-methyl (compounds la14, lb14 and lc14). Examples of these are compounds LA14, LB14 and LC14, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA14, LB14 and LC14, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA14, LB14 and LC14, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA14, LB14 and LC14, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA14, LB14 and LC14, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,4,6-Trifluor steht (Verbindungen l.a.15, l.b.15 und l.c.15). Beispiele hierfür sind Verbindungen l.a.15, l.b.15 und l.c.15, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.15, l.b.15 und l.c.15, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.15, l.b.15 und l.c.15, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.15, l.b.15 und l.c.15, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.15, l.b.15 und l.c.15, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,4,6-trifluoro (compounds la15, lb15 and lc15). Examples include compounds LA15, LB15 and LC15, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA15, LB15 and LC15, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA15, LB15 and LC15, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA15, LB15 and LC15, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA15, LB15 and LC15, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,6-Difluor-4-methoxy steht (Verbindungen La.16, l.b.16 und l.c.16). Beispiele hierfür sind Verbindungen l.a.16, l.b.16 und l.c.16, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.16, l.b.16 und l.c.16, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.16, l.b.16 und l.c.16, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.16, l.b.16 und l.c.16, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.16, l.b.16 und l.c.16, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2,6-difluoro-4-methoxy (compounds La.16, LB16 and LC16). Examples include compounds LA16, LB16 and LC16, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA16, LB16 and LC16, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA16, LB16 and LC16, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA16, LB16 and LC16, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA16, LB16 and LC16, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formei La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,3,4,5,6-Pentafluor steht (Verbindungen l.a.17, l.b.17 und l.c.17). Beispiele hierfür sind Verbindungen l.a.17, l.b.17 und Lc.17, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.17, l.b.17 und l.c.17, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.17, l.b.17 und l.c.17, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.17, l.b.17 und Lc.17, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.17, l.b.17 und Lc.17, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to use as a fungicide are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2,3,4,5,6-pentafluoro (compounds la17, lb17 and lc17). Examples include compounds LA17, LB17 and Lc.17, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA17, LB17 and LC17, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA17, LB17 and LC17, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA17, LB17 and Lc.17, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la17, lb17 and Lc.17, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2-Methyl-4-fluor steht (Verbindungen l.a.18, l.b.18 und l.c.18). Beispiele hierfür sind Verbindungen l.a.18, l.b.18 und l.c.18, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.18, l.b.18 und l.c.18, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindun- gen l.a.18, l.b.18 und l.c.18, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.18, l.b.18 und l.c.18, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.18, l.b.18 und l.c.18, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-methyl-4-fluorine (compounds la18, lb18 and lc18). Examples include compounds LA18, LB18 and LC18, in which R 2 and R 1 each represent hydroxy. Examples include compounds LA18, LB18 and LC18, in which R 2 and R 1 each represent chlorine. Examples include connections gen la18, lb18 and lc18, wherein R 2 is methyl and R 1 is chlorine. Examples of these are also compounds la18, lb18 and lc18, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la18, lb18 and lc18, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel a, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2-Fluor-6-methoxy steht (Verbindungen La.19, l.b.19 und l.c.19). Beispiele hierfür sind Verbindungen l.a.19, l.b.19 und l.c.19, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.19, l.b.19 und l.c.19, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.19, l.b.19 und l.c.19, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.19, l.b.19 und l.c.19, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.19, l.b.19 und l.c.19, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicide are also the compounds of the general formulas a, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-fluoro-6-methoxy (compounds La.19, lb19 and lc19). Examples include compounds LA19, LB19 and LC19, in which R 2 and R 1 each represent hydroxy. Examples include compounds LA19, LB19 and LC19, in which R 2 and R 1 each represent chlorine. Examples include compounds LA19, LB19 and LC19, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA19, LB19 and LC19, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la19, lb19 and lc19, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,4-Difluor steht (Verbindungen l.a.20, l.b.20 und l.c.20). Beispiele hierfür sind Verbindungen l.a.20, l.b.20 und l.c.20, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.20, l.b.20 und l.c.20, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.20, l.b.20 und l.c.20, worin R2 Methyl bedeutet und R Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.20, l.b.20 und l.c.20, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.20, l.b.20 und l.c.20, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,4-difluoro (compounds LA20, LB20 and LC20). Examples of these are compounds LA20, LB20 and LC20, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA20, LB20 and LC20, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA20, LB20 and LC20, in which R 2 is methyl and R is chlorine. Examples of these are also compounds LA20, LB20 and LC20, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA20, LB20 and LC20, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel a, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2-Fluor-4-chlor steht (Verbindungen l.a.21 , l.b.21 und l.c.21). Beispiele hierfür sind Verbindungen l.a.21, l.b.21 und l.c.21, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.21, l.b.21 und l.c.21, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.21, l.b.21 und l.c.21, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.21, l.b.21 und l.c.21, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.21 , l.b.21 und l.c.21 , worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as a fungicide are also the compounds of the general formula a, Ib and lc, where R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-fluoro-4-chlorine (compounds la21, lb21 and lc21). Examples include compounds LA21, LB21 and LC21, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA21, LB21 and LC21, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA21, LB21 and LC21, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA21, LB21 and LC21, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la21, lb21 and lc21, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2-Chlor-4-fluor steht (Verbindungen l.a.22, Lb.22 und l.c.22). Beispiele hierfür sind Verbindungen l.a.22, Lb.22 und l.c.22, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.22, Lb.22 und l.c.22, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.22, Lb.22 und l.c.22, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.22, Lb.22 und l.c.22, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.22, Lb.22 und l.c.22, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n is 2-chloro-4-fluorine (compounds la22, lb.22 and lc22). Examples include compounds LA22, Lb.22 and LC22, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA22, Lb.22 and LC22, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA22, Lb.22 and LC22, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA22, Lb.22 and LC22, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA22, Lb.22 and LC22, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,3-Difluor steht (Verbindungen l.a.23, l.b.23 und Lc.23). Beispiele hierfür sind Verbindungen l.a.23, l.b.23 und Lc.23, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.23, l.b.23 und Lc.23, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.23, l.b.23 und Lc.23, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.23, l.b.23 und Lc.23, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.23, l.b.23 und Lc.23, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,3-difluoro (compounds la23, lb23 and Lc.23). Examples of these are compounds la23, lb23 and Lc.23, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds la23, lb23 and Lc.23, in which R 2 and R 1 are each chlorine. Examples of these are also compounds la23, lb23 and Lc.23, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds la23, lb23 and Lc.23, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la23, lb23 and Lc.23, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,5-Difluor steht (Verbindungen l.a.24, l.b.24 und l.c.24). Beispiele hierfür sind Verbindungen l.a.24, l.b.24 und l.c.24, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.24, l.b.24 und l.c.24, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.24, l.b.24 und l.c.24, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.24, l.b.24 und l.c.24, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.24, l.b.24 und l.c.24, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,5-difluoro (compounds la24, lb24 and lc24). Examples include compounds LA24, LB24 and LC24, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA24, LB24 and LC24, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds LA24, LB24 and LC24, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds LA24, LB24 and LC24, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds LA24, LB24 and LC24, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 , R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,3,4-Trifluor steht (Verbindungen l.a.25, l.b.25 und l.c.25). Beispiele hierfür sind Verbindungen l.a.25, l.b.25 und l.c.25, worin R2 und R1 für jeweils Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.25, l.b.25 und l.c.25, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.25, l.b.25 und l.c.25, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.25, l.b.25 und l.c.25, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.25, l.b.25 und l.c.25, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n stands for 2,3,4-trifluoro (compounds la25, lb25 and lc25). Examples include compounds LA25, LB25 and LC25, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA25, LB25 and LC25, in which R 2 and R 1 each represent chlorine. Examples of these are also compounds la25, lb25 and lc25, in which R 2 is methyl and R 1 is chlorine. Examples of these are also compounds la25, lb25 and lc25, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la25, lb25 and lc25, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Besonders bevorzugte Verbindungen der allgemeinen Formel I im Hinblick auf die Verwendung als Fungizid sind weiterhin die Verbindungen der allgemeinen Formel La, l.b und l.c, worin R3 und R4 jeweils für Wasserstoff stehen, R2 für Hydroxy, Chlor oder Methyl steht und (Ra)n für 2,4-Dimethyl steht (Verbindungen l.a.26, l.b.26 und l.c.26). Beispiele hierfür sind Verbindungen l.a.26, l.b.26 und l.c.26, worin R2 und R1 jeweils für Hydroxy stehen. Beispiele hierfür sind auch Verbindungen l.a.26, l.b.26 und l.c.26, worin R2 und R1 jeweils Chlor bedeuten. Beispiele hierfür sind auch Verbindungen l.a.26, l.b.26 und l.c.26, worin R2 Methyl bedeutet und R1 Chlor bedeutet. Beispiele hierfür sind auch Verbindungen l.a.26, l.b.26 und l.c.26, worin R2 Chlor bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen. Beispiele hierfür sind auch Verbindungen l.a.26, l.b.26 und l.c.26, worin R2 Methyl bedeutet und R1 für NR7R8 steht, wobei R7, R8 gemeinsam jeweils die in einer Zeile der Tabelle A angegebenen Bedeutungen aufweisen.Particularly preferred compounds of the general formula I with regard to their use as fungicides are also the compounds of the general formulas La, lb and lc, in which R 3 and R 4 are each hydrogen, R 2 is hydroxyl, chlorine or methyl and (R a ) n represents 2,4-dimethyl (compounds la26, lb26 and lc26). Examples include compounds LA26, LB26 and LC26, in which R 2 and R 1 each represent hydroxy. Examples of these are also compounds LA26, LB26 and LC26, in which R 2 and R 1 each represent chlorine. Examples of this are connections la26, lb26 and lc26, wherein R 2 is methyl and R 1 is chlorine. Examples of these are also compounds la26, lb26 and lc26, in which R 2 is chlorine and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A. Examples of these are also compounds la26, lb26 and lc26, in which R 2 is methyl and R 1 is NR 7 R 8 , where R 7 and R 8 together each have the meanings given in one row of Table A.
Die erfindungsgemäßen Verbindungen der Formel I können in Analogie zu an sich be- kannten Verfahren des Standes der Technik nach den in den folgenden Schemata dargestellten Synthesen hergestellt werden:The compounds of the formula I according to the invention can be prepared analogously to processes known per se from the prior art by the syntheses shown in the following schemes:
Schema 1 :Scheme 1:
In Schema 1 haben n, Ra, R , R2, R3, X und Y die zuvor genannten Bedeutungen. R steht für C C4-Alkyl, insbesondere für Methyl oder Ethyl, W steht für CrCe-Alkyl, C Ce-Alkoxy, insbesondere für Methoxy oder Ethoxy, CrC6-Halogenalkyl, gegebenenfalls substituiertes C3-C8-Cycloalkyl, gegebenenfalls substituiertes C5-C8-Cycloalkenyl, C2- C6-Alkenyl oder C2-C6-Alkinyl und U steht für OH, CrCe-Alkyl, C C6-Halogenalkyl, gegebenenfalls substituiertes C3-C8-Cycloalkyl, gegebenenfalls substituiertes C5-C8- Cycloalkenyl, C2-C6-Alkenyl oder C2-C6-Alkinyl.In scheme 1, n, R a , R, R 2 , R 3 , X and Y have the meanings mentioned above. R stands for CC 4 -alkyl, in particular for methyl or ethyl, W stands for CrCe-alkyl, C Ce-alkoxy, in particular for methoxy or ethoxy, CrC 6 -haloalkyl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted C 5 -C 8 cycloalkenyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl and U represents OH, CrCe alkyl, CC 6 haloalkyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted C 5 -C 8 cycloalkenyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl.
Gemäß Schema 1 wird in einem ersten Schritt ein Hetarylamin der allgemeinen Formel II mit einer CH-aciden Verbindung der allgemeinen Formel III kondensiert. Beispiele für geeignete CH-acide Verbindungen der allgemeinen Formel III sind substituierte Phe- nylessigsäure-(CrC4)-alkylester und substituierte Benzyl(halogen)alkylketone, Benzyl- cycloalkylketone, Benzylalkenylketone, Benzylcycloalkenylketone und Benzylalkinylke- tone. Beispiele für geeignete Hetarylamine der allgemeinen Formel II sind 2-Amino- pyridin-3-carbonsäureester (2-Aminonicotinsäureester), 3-Aminopyrazin-2-carbon- säureester und 4-Aminopyrimidin-5-carbonsäureester.According to Scheme 1, a hetarylamine of the general formula II is condensed with a CH-acidic compound of the general formula III in a first step. Examples of suitable CH-acidic compounds of the general formula III are substituted phenylacetic acid (CrC 4 ) alkyl esters and substituted benzyl (halogen) alkyl ketones, benzyl cycloalkyl ketones, benzylalkenyl ketones, benzylcycloalkenyl ketones and benzylalkynyl ketones. Examples of suitable hetarylamines of the general formula II are 2-amino pyridine-3-carboxylic acid ester (2-aminonicotinic acid ester), 3-aminopyrazine-2-carboxylic acid ester and 4-aminopyrimidine-5-carboxylic acid ester.
So erhält man beim Einsatz von 2-Aminopyridin-3-carbonsäureester (2-Aminonicotin- säureester) die Verbindungen La mit R1 = OH; beim Einsatz von 3-Aminopyrazin-2- carbonsäureester die Verbindungen l.b mit R1 = OH und beim Einsatz von 4- Aminopyrimidin-5-carbonsäureester die Verbindungen l.c mit R1 = OH.Thus, when using 2-aminopyridine-3-carboxylic acid ester (2-aminonicotinic acid ester), the compounds La with R 1 = OH; when using 3-aminopyrazine-2-carboxylic acid ester the compounds lb with R 1 = OH and when using 4-aminopyrimidine-5-carboxylic acid ester the compounds lc with R 1 = OH.
Die Kondensation erfolgt in der Regel in Gegenwart einer Brönstedt- oder Lewissäure als saurem Katalysator oder in Gegenwart eines basischen Katalysators, siehe z. B. Organikum, 15. Auflage, VEB Deutscher Verlag der Wissenschaften, Berlin 1976, 552ff. Beispiele für geeignete saure Katalysatoren sind Zinkchlorid, Phosphorsäure, Salzsäure, Essigsäure sowie Mischungen aus Essigsäure und Zinkchlorid. Beispiele für geeignete basische Katalysatoren sind anorganische und organische basische Ka- talysatoren. Geeignete anorganische basische Katalysatoren sind beispielsweise Alkali- oder Erdalkalihydride, vorzugsweise Alkalimetallhydride wie Natriumhydrid oder Kaliumhydrid und Alkali- und Erdalkalimetallhydroxide wie Natriumhydroxid oder Kaliumhydroxid. Weiterhin kann die Kondensation bei Einsatz von substituiertem Phenyles- sigsäureester in Gegenwart von metallischem Natrium erfolgen. Beispiele für geeignete organische basische Katalysatoren sind Alkali- oder Erdalkalimetallalkoxide wie Natri- ummethylat, Natriumethylat, Natrium-n-propylat, Natriumisopropylat, Natrium-n-butylat, Natrium-sec-butylat, Natrium-tert-butylat, Kaliummethylat, Kaliumethylat, Kalium-n-pro- pylat, Kaliumisopropylat, Kalium-n-butylat, Kalium-sec-butylat, Kalium-tert-butylat, sekundäre Amine wie Ethyldiisopropylamin und Amidinbasen wie 1 ,5-Diazabicyclo- [4.3.0]non-5-en (DBN) oder 1 ,8-Diazabicyclo[5.4.0]undec-7-en (DBU).The condensation is usually carried out in the presence of a Brönstedt or Lewis acid as an acid catalyst or in the presence of a basic catalyst, see e.g. B. Organikum, 15th edition, VEB German Publishing House of Sciences, Berlin 1976, 552ff. Examples of suitable acidic catalysts are zinc chloride, phosphoric acid, hydrochloric acid, acetic acid and mixtures of acetic acid and zinc chloride. Examples of suitable basic catalysts are inorganic and organic basic catalysts. Suitable inorganic basic catalysts are, for example, alkali or alkaline earth metal hydrides, preferably alkali metal hydrides such as sodium hydride or potassium hydride and alkali and alkaline earth metal hydroxides such as sodium hydroxide or potassium hydroxide. Furthermore, the condensation can be carried out in the presence of metallic sodium when using substituted phenylacetic acid ester. Examples of suitable organic basic catalysts are alkali metal or alkaline earth metal alkoxides such as sodium methylate, sodium ethylate, sodium n-propylate, sodium isopropylate, sodium n-butoxide, sodium sec-butoxide, sodium tert-butoxide, potassium methylate, potassium ethylate, potassium n-propylate, potassium isopropylate, potassium n-butoxide, potassium sec-butoxide, potassium tert-butoxide, secondary amines such as ethyldiisopropylamine and amidine bases such as 1,5-diazabicyclo- [4.3.0] non-5-ene ( DBN) or 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU).
Die Umsetzung kann in Abwesenheit eines Lösungsmittels oder in einem Lösungsmittel durchgeführt werden. Bei Abwesenheit eines Lösungsmittels setzt man die CH- acide Verbindung III in der Regel im Überschuss, bezogen auf das Hetarylamin, ein.The reaction can be carried out in the absence of a solvent or in a solvent. In the absence of a solvent, the CH-acidic compound III is generally used in excess, based on the hetarylamine.
Kondensationsreaktionen zwischen einem Hetarylamin der allgemeinen Formel II mit einem geeignet substituiertem Phenylessigsäureester der allgemeinen Formel III sind aus der Literatur prinzipiell bekannt, z. B. aus Archiv der Pharmazie, 290, 1957, 136, Chem. Ber. 96, 1963, 1868, Chem. Ber. 111, 1978, 2813 - 2824 oder J. Heterocyclic Chem. 30, 909 (1963) und können in analoger Weise zur Herstellung der erfindungsgemäßen Verbindungen genutzt werden.Condensation reactions between a hetarylamine of the general formula II with a suitably substituted phenylacetic acid ester of the general formula III are known in principle from the literature, for. B. from Archives of Pharmacy, 290, 1957, 136, Chem. Ber. 96, 1963, 1868, Chem. Ber. 111, 1978, 2813-2824 or J. Heterocyclic Chem. 30, 909 (1963) and can be used in an analogous manner for the preparation of the compounds according to the invention.
Bei der in Schema 1 gezeigten Kondensation erhält man bei Verwendung von Phenyl- essigsäureestem der allgemeinen Formeln III Verbindungen I, worin R1 und R2 jeweils für Hydroxy stehen. Bei Verwendung von Ketonen der allgemeinen Formel III erhält man Verbindungen I mit R1 = Hydroxy und R2 = CrC6-(Halogen)alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, gegebenenfalls substituiertes C3-C8-Cycloalkyl oder gegebenenfalls substituiertes C5-C8-Cycloalkenyl.In the condensation shown in Scheme 1, when using phenylacetic esters of the general formulas III, compounds I are obtained in which R 1 and R 2 are each hydroxyl. When using ketones of the general formula III is obtained compounds I with R 1 = hydroxy and R 2 = CrC 6 - (halo) alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, optionally substituted C 3 -C 8 cycloalkyl or optionally substituted C 5 -C 8 cycloalkenyl.
Derartige Verbindungen I (R1 = OH) sind als Zwischenprodukte für die Herstellung anderer Verbindungen I von besonderem Interesse. Die OH-Gruppe(n) in diesen Verbindungen kann (können) in einem oder mehreren Schritten in andere funktioneile Gruppen umgewandelt werden. In der Regel wird man hierzu zunächst die OH-Gruppe(n) in Halogen, insbesondere Chlor überführen (siehe Schema 1a).Such compounds I (R 1 = OH) are of particular interest as intermediates for the preparation of other compounds I. The OH group (s) in these compounds can be converted into other functional groups in one or more steps. As a rule, the OH group (s) will first be converted into halogen, especially chlorine (see Scheme 1a).
Schema 1a:Scheme 1a:
(I: R1 = Cl; R2 = Cl) (I: R 1 = Cl; R 2 = Cl)
(I: R1 = Cl; (I: R1 = OH; R2 = Alkyl, Halogenalkyl, R2 = Alkyl, Halogenalkyl, Cycloalkyl) Cycloalkyl) (I: R 1 = Cl; (I: R 1 = OH; R 2 = alkyl, haloalkyl, R 2 = alkyl, haloalkyl, cycloalkyl) cycloalkyl)
In Schema 1a haben die Variablen n, Ra, R3, X und Y die zuvor genannten Bedeutungen. Diese Umwandlung gelingt beispielsweise durch Umsetzung von I {R1 = OH, R2 = OH, CrC6-(Halogen)alkyl, gegebenenfalls substituiertes C3-C8-Cycloalkyl } mit einem geeigneten Halogenierungsmittel (in Schema 1a für ein Chlorierungsmittel [Cl] gezeigt). Diese Methode ist prinzipiell bekannt, z. B. aus Archiv der Pharmazie, 290, 1957, S. 136 oder J. Heterocyclic Chem., 30, 909 (1993).In scheme 1a, the variables n, R a , R 3 , X and Y have the meanings mentioned above. This conversion is achieved, for example, by reacting I {R 1 = OH, R 2 = OH, CrC 6 - (halogen) alkyl, optionally substituted C 3 -C 8 -cycloalkyl} with a suitable halogenating agent (in scheme 1a for a chlorinating agent [Cl ] shown). This method is known in principle, e.g. B. from Archiv der Pharmazie, 290, 1957, p. 136 or J. Heterocyclic Chem., 30, 909 (1993).
Als Halogenierungsmittel eignen sich beispielsweise Phosphortrihalogenide, Phosphor- oxyhalogenide oder Phosphorpentahalogenide wie Phosphortribromid, Posphoroxy- tribromid, und insbesondere Chlorierungsmittel wie POCI3, PC C\2 oder PCI5, und Mischungen dieser Reagenzien. Vorzugsweise verwendet man für die Chlorierung ein Gemisch aus Phosphorpentachlorid und Phosphoroxychlorid. Die Reaktion kann in überschüssigem Halogenierungsmittel (POCI3) oder einem inerten Lösungsmittel, wie beispielsweise Acetonitril oder 1 ,2-Dichlorethan durchgeführt werden.Examples of suitable halogenating agents are phosphorus trihalides, phosphorus oxyhalides or phosphorus pentahalides, such as phosphorus tribromide, phosphorus oxytribromide, and in particular chlorinating agents, such as POCI 3 , PC C \ 2 or PCI 5 , and mixtures of these reagents. A mixture of phosphorus pentachloride and phosphorus oxychloride is preferably used for the chlorination. The reaction can occur in excess halogenating agent (POCI 3 ) or an inert solvent such as acetonitrile or 1, 2-dichloroethane.
Diese Umsetzung erfolgt üblicherweise zwischen 10 und 180 °C. Aus praktischen Gründen entspricht häufig die Reaktionstemperatur der Siedetemperatur des eingesetzten Chlorierungsmittels (POCI3) oder des Lösungsmittels. Das Verfahren wird gegebenenfalls unter Zusatz von N,N-Dimethylformamid oder von Stickstoff basen, wie beispielsweise N,N-Dimethylanilin in katalytischen oder stöchiometrischen Mengen durchgeführt.This reaction usually takes place between 10 and 180 ° C. For practical reasons, the reaction temperature often corresponds to the boiling point of the chlorinating agent (POCI 3 ) or solvent used. The process is optionally carried out with the addition of N, N-dimethylformamide or nitrogen bases, such as N, N-dimethylaniline in catalytic or stoichiometric amounts.
Die hierbei erhaltenen Monohalogenverbindungen I, z. B. die Chlorverbindung I {R1 = Cl; R2 = CrC6-(Halogen)alkyl, gegebenenfalls substituiertes C3-C8-Cycloalkyl) oder die Dichlorverbindung I { R1 = R2 = Cl} können dann in Analogie zu bekannten Verfahren aus dem Stand der Technik in andere Verbindungen I umgewandelt werden.The monohalogen compounds I obtained, for. B. the chlorine compound I {R 1 = Cl; R 2 = CrC 6 - (halogen) alkyl, optionally substituted C 3 -C 8 -cycloalkyl) or the dichloro compound I {R 1 = R 2 = Cl} can then be converted into other compounds I in analogy to known processes from the prior art being transformed.
Verbindungen der Formel I, worin R1 für OR6 steht, werden aus den entsprechenden Chlorverbindungen der Formel I {R1 = Cl, R2 = Alkyl, Halogenalkyl, Cycloalkyl} durch Umsetzung mit Alkalimetallhydroxiden {OR6 = OH}, Alkali- oder Erdalkalimetallalkoho- laten {OR6 = O-Alkyl, O-Halogenalkyl} erhalten [vgl.: Heterocycles, Bd. 32, S. 1327- 1340 (1991); J. Heterocycl. Chem. Bd. 19, S. 1565-1567 (1982); Geterotsikl. Soedin, S. 400-402 (1991)]. Veresterung von Verbindungen mit R1 = OH nach an sich bekannten Methoden liefert Verbindungen I, worin R1 für O-C(O)R9 steht. Verbindungen mit R1 = OH können auch nach an sich bekannten Methoden der Veretherung in die entsprechenden Verbindungen I überführt werden, worin R für O-Alkyl, O-Halogenalkyl oder O-Alkenyl steht.Compounds of formula I, wherein R 1 is OR 6 , from the corresponding chlorine compounds of formula I {R 1 = Cl, R 2 = alkyl, haloalkyl, cycloalkyl} by reaction with alkali metal hydroxides {OR 6 = OH}, alkali or Alkaline earth metal alcoholates {OR 6 = O-alkyl, O-haloalkyl} obtained [cf. Heterocycles, vol. 32, pp. 1327-1340 (1991); J. Heterocycl. Chem. Vol. 19, pp. 1565-1567 (1982); Geterotsikl. Soedin, pp. 400-402 (1991)]. Esterification of compounds with R 1 = OH by methods known per se provides compounds I in which R 1 is OC (O) R 9 . Compounds with R 1 = OH can also be converted into the corresponding compounds I, in which R is O-alkyl, O-haloalkyl or O-alkenyl, by methods of etherification which are known per se.
Verbindungen der Formel I, in der R1 für Cyano steht, können aus den entsprechenden Chlorverbindungen der Formel I {R = Cl, R2 = Alkyl, Halogenalkyl, Cycloalkyl} durch Umsetzung mit Alkali-, Erdalkalimetall- oder Metallcyaniden, wie NaCN, KCN oder Zn(CN)2, erhalten werden [vgl.: Heterocycles, Bd. 39, S. 345-356 (1994); Collect.Compounds of the formula I in which R 1 is cyano can be obtained from the corresponding chlorine compounds of the formula I {R = Cl, R 2 = alkyl, haloalkyl, cycloalkyl} by reaction with alkali metal, alkaline earth metal or metal cyanides, such as NaCN, KCN or Zn (CN) 2 can be obtained [see: Heterocycles, vol. 39, pp. 345-356 (1994); Collect.
Czech. Chem. Commun. Bd. 60, S. 1386-1389 (1995); Acta Chim. Scand., Bd. 50, S. 58-63 (1996)]Czech. Chem. Commun. Vol. 60, pp. 1386-1389 (1995); Acta Chim. Scand., Vol. 50, pp. 58-63 (1996)]
Verbindungen der allgemeinen Formel I, worin R1 für Halogen steht sowie Verbindun- gen der allgemeinen Formel I, worin R1 und R2 gleichzeitig für Halogen stehen, sind daher als Zwischenprodukte für die Herstellung anderer Verbindungen I von besonderem Interesse. Einen Überblick über weitere derartige Umwandlungen geben die Schemata 1b, 1c und 1d. So kann man beispielsweise, wie in Schema 1b gezeigt, die Monochlorverbindung I {R1 = Cl, R2 = CrC6-(Halogen)alkyl, gegebenenfalls substituiertes C3-C8-Cycloalkyl} mit einem Amin HNR7R8, worin R7 und R8 die zuvor genannten Bedeutungen aufweisen, umsetzen, wobei man eine Verbindung I erhält, worin R für NR7R8 steht und R2 für d- C6-(Halogen)alkyl, gegebenenfalls substituiertes C3-C8-Cycloalkyl steht. Setzt man die Dichlorverbindung I {R1 = R2 = Cl) mit einem Amin HNR7R8 um, worin R7 und R8 die zuvor genannten Bedeutungen aufweisen, so erhält man eine Verbindung I, worin R1 für Chlor steht und R2 für NR7R8 steht.Compounds of the general formula I in which R 1 is halogen and compounds of the general formula I in which R 1 and R 2 are simultaneously halogen are therefore of particular interest as intermediates for the preparation of other compounds I. Schemes 1b, 1c and 1d provide an overview of other such conversions. For example, as shown in Scheme 1b, the monochloro compound I {R 1 = Cl, R 2 = CrC 6 - (halogen) alkyl, optionally substituted C 3 -C 8 cycloalkyl} with an amine HNR 7 R 8 , in which R 7 and R 8 have the meanings given above, to give a compound I in which R is NR 7 R 8 and R 2 is d- C 6 - (halogen) alkyl, optionally substituted C 3 -C 8 - Cycloalkyl is. Reacting the dichloro compound I {R 1 = R 2 = Cl) with an amine HNR 7 R 8 , in which R 7 and R 8 have the meanings given above, gives a compound I in which R 1 is chlorine and R 2 stands for NR 7 R 8 .
Schema lb:Scheme lb:
(I: R1 = NR7RΘ; R2 = Alkyl, Halogenalkyl, Cycloalkyl) (I: R 1 = NR 7 R Θ ; R 2 = alkyl, haloalkyl, cycloalkyl)
(I: R1 = R2 = Cl) (I: R 1 = R 2 = Cl)
In Schema 1b haben die Variablen n, Ra, R3, R7, R8, X und Y die zuvor genannten Bedeutungen.In scheme 1b, the variables n, R a , R 3 , R 7 , R 8 , X and Y have the meanings mentioned above.
Die Umsetzung der Monochlorverbindung I {R1 = Cl, R2 = CrC6-Alkyl, CrCe-Halogenalkyl oder gegebenenfalls substituiertes C3-C8-Cycloalkyl} oder der Dichlorverbindun- gen I {R = R2 = Cl} mit einem Amin HNR7R8 erfolgt üblicherweise bei 0 bis 150 °C, vorzugsweise bei 10 bis 120 °C in einem inerten Lösungsmittel, gegebenenfalls in Gegenwart einer Hilfsbase. Diese Methode ist prinzipiell bekannt, z.B. aus II Farmaco, 57, 2002, 631 und kann in analoger Weise zur Herstellung der erfindungsgemäßen Verbindungen angewendet werden.The reaction of the monochloro compound I {R 1 = Cl, R 2 = CrC 6 alkyl, CrCe haloalkyl or optionally substituted C 3 -C 8 cycloalkyl} or the dichloro compounds I {R = R 2 = Cl} with an amine HNR 7 R 8 is usually carried out at 0 to 150 ° C, preferably at 10 to 120 ° C in an inert solvent, optionally in the presence of an auxiliary base. This method is known in principle, for example from II Farmaco, 57, 2002, 631, and can be used in an analogous manner for the preparation of the compounds according to the invention.
Als Lösungsmittel kommen protische Lösungsmittel, wie Alkohole, beispielsweise E- thanol, sowie aprotische Lösungsmittel, beispielsweise aromatische Kohlenwasserstoffe, Halogenkohlenwasserstoff und Ether, z.B. Toluol, o-, m- und p-Xylol, Diethyl- ether, Diisopropylether, tert.-Butylmethylether, Dioxan Tetrahydrofuran, Dichlormethan, sowie Mischungen der vorgenannten Lösungsmittel, in Betracht. Geeignete Hilfsbasen sind beispielsweise die im Folgenden genannten: Alkalimetallcarbonate und -hydrogen- carbonate wie NaHCO3, und Na2CO3, Alkalimetallhydrogenphosphate wie Na2HPO4, Alkalimetallborate wie Na2B4O7, tertiäre Amine wie Triethylamin, Ethyldiisopropylamin oder Diethylanilin und Pyridinverbindungen. Als Hilfsbase kommt auch ein Uberschuss des Amins HNR7R8in Betracht.Protic solvents such as alcohols, for example ethanol, and aprotic solvents, for example aromatic hydrocarbons, halogenated hydrocarbon and ethers, for example toluene, o-, m- and p-xylene, diethyl- ether, diisopropyl ether, tert-butyl methyl ether, dioxane, tetrahydrofuran, dichloromethane, and mixtures of the abovementioned solvents. Suitable auxiliary bases are, for example, those mentioned below: alkali metal carbonates and hydrogen carbonates such as NaHCO 3 and Na 2 CO 3 , alkali metal hydrogen phosphates such as Na 2 HPO 4 , alkali metal borates such as Na 2 B 4 O 7 , tertiary amines such as triethylamine, ethyldiisopropylamine or diethylaniline and pyridine compounds. An excess of the amine HNR 7 R 8 can also be used as an auxiliary base.
Üblicherweise werden die Komponenten in etwa stöchiometrischem Verhältnis einge- setzt. Es kann jedoch vorteilhaft sein, das Amin HNR7R8 im Uberschuss einzusetzen. Bei Verwendung eines Überschusses an Amin HNR7R8, kann das Amin gleichzeitig als Lösungsmittel fungieren.The components are usually used in an approximately stoichiometric ratio. However, it may be advantageous to use the amine HNR 7 R 8 in excess. If an excess of amine HNR 7 R 8 is used , the amine can simultaneously act as a solvent.
Die Amine HNR7R8 sind käuflich oder literaturbekannt oder können nach bekannten Methoden hergestellt werden.The amines HNR 7 R 8 are commercially available or known from the literature or can be prepared by known methods.
Verbindungen der Formel I, worin R2 für O-CrC4-Alkyl-phenyl steht, wobei Phenyl gegebenenfalls ein- oder mehrfach substituiert ist, lassen sich auch aus der entsprechenden Dichlorverbindung I {R1 = Cl, R2 = Cl} durch Umsetzung mit einem Alkohol R6OH wie in Schema 1c gezeigt herstellen. Solche Umsetzungen sind prinzipiell bekannt, beispielsweise aus JACS, 69, 1947, 1204. Die Umsetzung erfolgt in der Regel in Gegenwart einer Base. Geeignete Basen sind Alkalimetallhydride, wie Natriumhydrid oder Kaliumhydrid, Alkali- oder Erdalkalimetallalkoxide wie Natrium-t-butylat oder Kalium- tert-butylat oder tertiäre Amine wie Triethylamin oder Pyridin. Alternativ kann man auch den Alkohol R6OH zunächst mit einem Alkalimetall, vorzugsweise Natrium, unter Bildung des entsprechenden Alkoholats umsetzen. Die Reaktion kann in überschüssigem Alkohol oder in einem inerten Lösungsmittel wie Carbonsäureamide beispielsweise N,N-Dimethylformamid, N,N-Dimethylacetamid, N-Methylpyrrolidon durchgeführt werden. Die Umsetzung erfolgt üblicherweise bei 0 °C bis 150 °C, vorzugsweise bei 10 °C bis 100 °C.Compounds of the formula I in which R 2 is O-CrC 4 -alkylphenyl, where phenyl is optionally mono- or polysubstituted, can also be reacted from the corresponding dichloro compound I {R 1 = Cl, R 2 = Cl} with an alcohol R 6 OH as shown in Scheme 1c. Such reactions are known in principle, for example from JACS, 69, 1947, 1204. The reaction is usually carried out in the presence of a base. Suitable bases are alkali metal hydrides such as sodium hydride or potassium hydride, alkali or alkaline earth metal alkoxides such as sodium t-butoxide or potassium tert-butoxide or tertiary amines such as triethylamine or pyridine. Alternatively, the alcohol R 6 OH can first be reacted with an alkali metal, preferably sodium, to form the corresponding alcoholate. The reaction can be carried out in excess alcohol or in an inert solvent such as carboxamides, for example N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone. The reaction is usually carried out at 0 ° C to 150 ° C, preferably at 10 ° C to 100 ° C.
Schema 1c:Scheme 1c:
(I: R1 = Cl; R2 = OR6 mit R6 = Phenyl-CrC^alkyl) In Schema 1c haben n, Ra, R3, X und Y die zuvor genannten Bedeutungen und der Phenylrest in R6 kann gegebenenfalls ein- oder mehrfach durch Alkyl, Alkoxy oder Halogen substituiert sein.(I: R 1 = Cl; R 2 = OR 6 with R 6 = phenyl-CrC ^ alkyl) In Scheme 1c, n, R a , R 3 , X and Y have the meanings mentioned above and the phenyl radical in R 6 can optionally be substituted one or more times by alkyl, alkoxy or halogen.
Verbindungen der Formel I, worin R1 für NR7R8 steht und R2 für Halogen, insbesondere Chlor, steht, können beispielsweise aus den entsprechenden Halogenverbindungen der Formel I {R1 = Halogen, R2 = OR6 mit R6 = Phenyl-C C4-alkyl) erhalten werden. Die Reaktionssequenz ist in Schema 1d für die Herstellung von Verbindungen I mit R1 = NR7R8 und R2 = Cl gezeigt. In Schema 1d haben n, Ra, R3, R7, R8, X und Y die zuvor genannten Bedeutungen und der Phenylrest in R6 kann gegebenenfalls ein- oder mehrfach durch Alkyl, Alkoxy oder Halogen substituiert sein.Compounds of the formula I in which R 1 is NR 7 R 8 and R 2 is halogen, in particular chlorine, can, for example, from the corresponding halogen compounds of the formula I {R 1 = halogen, R 2 = OR 6 with R 6 = phenyl -C C 4 alkyl) can be obtained. The reaction sequence is shown in Scheme 1d for the preparation of compounds I with R 1 = NR 7 R 8 and R 2 = Cl. In Scheme 1d, n, R a , R 3 , R 7 , R 8 , X and Y have the meanings mentioned above and the phenyl radical in R 6 can optionally be substituted one or more times by alkyl, alkoxy or halogen.
Schema 1d:Scheme 1d:
(I: R8; (I: R 8 ;
Die in Schritt a) dargestellte Umsetzung kann in an sich bekannter Weise, beispielsweise in Analogie zu der in Schema 1b angegebenen Methode, erfolgen. In der erhaltenen Verbindung I {R1 = NR7R8 und R2 = OR6 mit R6 = Phenyl-C C4-alkyl} lässt sich die Etherbindung durch katalytische Hydrogenolse, z. B. nach der aus Org. Lett., 3, 2001 , 4263 beschrieben Methode, spalten. Geeignete Katalysatoren sind beispielsweise Edelmetalle oder Übergangsmetalle wie Palladium oder Platin. In der Regel ist der Katalysator geträgert, beispielsweise auf Aktivkohle. Die Hydrogenolyse erfolgt üblicherweise in einem Lösungsmittel. Geeignete Lösungsmittel sind beispielsweise Alkohole wie Methanol oder cyclische Ether wie Tetrahydrofuran oder Dioxan. In der Regel erfolgt die Hydrogenolyse bei Normaldruck. Die Hydrogenolyse erfolgt in der Regel bei Temperaturen zwischen Raumtemperatur und der Siedetemperatur des Lösungsmittels, vorzugsweise bei Temperaturen zwischen Raumtemperatur und 40 °C. Die auf diese Weise erhaltenen Verbindungen der Formel I mit R1 = NR7R8 und R2 = OH lassen sich dann in die entsprechenden Verbindungen mit R1 = NR7R8 und R2 = Halogen, vorzugsweise Chlor, überführen. Verfahren zur Umwandlung von Alkoholen in die entsprechenden Halogenide sind aus dem Stand der Technik bekannt, z. B. aus J. Chem. Soc. 1947, 899. Geeignete Halogenierungsmittel sind beispielsweise die zuvor genannten Halogenierungsmittel (siehe Schema 1a). Die Umsetzung kann in überschüssigem Halogenierungsmittel, beispielsweise POCI3, oder in einem inerten Lösungsmittel wie Acetonitril oder 1 ,2-Dichlorethan durchgeführt werden.The reaction shown in step a) can be carried out in a manner known per se, for example in analogy to the method given in scheme 1b. In the compound I {R 1 = NR 7 R 8 and R 2 = OR 6 with R 6 = phenyl-C C 4 -alkyl} obtained, the ether linkage can be catalyzed by hydrogenolysis, e.g. B. split according to the method described in Org. Lett., 3, 2001, 4263. Suitable catalysts are, for example, noble metals or transition metals such as palladium or platinum. As a rule, the catalyst is supported, for example on activated carbon. Hydrogenolysis is usually carried out in a solvent. Suitable solvents are, for example, alcohols such as methanol or cyclic ethers such as tetrahydrofuran or dioxane. As a rule, hydrogenolysis takes place at normal pressure. Hydrogenolysis is generally carried out at temperatures between room temperature and the boiling point of the solvent, preferably at temperatures between room temperature and 40 ° C. The compounds of the formula I obtained in this way with R 1 = NR 7 R 8 and R 2 = OH can then be converted into the corresponding compounds with R 1 = NR 7 R 8 and R 2 = halogen, preferably chlorine. Methods for converting alcohols into the corresponding halides are known from the prior art, e.g. B. from J. Chem. Soc. 1947, 899. Suitable halogenating agents are, for example, the aforementioned halogenating agents (see scheme 1a). The reaction can be carried out in excess halogenating agent, for example POCI 3 , or in an inert solvent such as acetonitrile or 1,2-dichloroethane.
Die Umsetzung erfolgt in der Regel zwischen 10 und 180 °C, vorzugsweise zwischen Raumtemperatur und 130 °C.The reaction is usually carried out between 10 and 180 ° C, preferably between room temperature and 130 ° C.
Verbindungen der Formel I, in der R2 für Cyano steht, können aus den entsprechenden Chlorverbindungen der Formel I {R1 = NR7R8, R2 = Cl} durch Umsetzung mit Alkali-, Erdalkalimetall- oder Metallcyaniden, wie NaCN, KCN oder Zn(CN)2, erhalten werden [vgl.: Heterocycles, Bd. 39, S. 345-356 (1994); Collect. Czech. Chem. Commun. Bd. 60, S. 1386-1389 (1995); Acta Chim. Scand., Bd. 50, S. 58-63 (1996)].Compounds of the formula I in which R 2 is cyano can be obtained from the corresponding chlorine compounds of the formula I {R 1 = NR 7 R 8 , R 2 = Cl} by reaction with alkali metal, alkaline earth metal or metal cyanides, such as NaCN, KCN or Zn (CN) 2 can be obtained [see: Heterocycles, vol. 39, pp. 345-356 (1994); Collect. Czech. Chem. Commun. Vol. 60, pp. 1386-1389 (1995); Acta Chim. Scand., Vol. 50, pp. 58-63 (1996)].
Die Umwandlung von Chlorverbindungen der Formel I {R1 = NR7R8, R2 = Cl} in Verbindungen der Formel I, worin R2 für CrC6-Alkyl, CrC6-Halogenalkyl, C2-C6-Alkenyl, C2- C6-Alkinyl, gegebenenfalls substituiertes C3-C8-Cycloalkyl, gegebenenfalls substituiertes C5-C8-Cycloalkenyl steht, gelingt in an sich bekannter Weise durch Umsetzung mit metallorganischen Verbindungen R2a-Met, worin R2a für CrC6-Alkyl, CrC6-Halogen- alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, gegebenenfalls substituiertes C3-C8-Cycloalkyl, gegebenenfalls substituiertes C5-C8-Cycloalkenyl steht und Met Lithium, Magnesium oder Zink bedeutet. Die Umsetzung erfolgt vorzugsweise in Gegenwart katalytischer oder insbesondere wenigstens äquimolarer Mengen an Übergangsmetallsalzen und/oder - Verbindungen, insbesondere in Gegenwart von Cu-Salzen wie Cu(l)halogenide und speziell Cu(l)iodid. In der Regel erfolgt die Umsetzung in einem inerten organischen Lösungsmittel, beispielsweise einem Ether, insbesondere Tetrahydrofuran, einem a- liphatischen oder cycloaliphatischen Kohlenwasserstoff wie Hexan, Cyclohexan und dergleichen, einem aromatischen Kohlenwasserstoff wie Toluol oder in einer Mischung dieser Lösungsmittel. Die hierfür erforderlichen Temperaturen liegen im Bereich von -100 bis +100°C und speziell im Bereich von -80°C bis +40°C.The conversion of chloro compounds of the formula I {R 1 = NR 7 R 8, R 2 = Cl} in compounds of formula I, wherein R 2 is -C 6 alkyl, -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 - C 6 -alkynyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted C 5 -C 8 cycloalkenyl, can be achieved in a manner known per se by reaction with organometallic compounds R 2a -Met, in which R 2a is CrC 6 alkyl, halo-CrC 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -alkynyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted C 5 -C 8 cycloalkenyl, and Met is lithium, Magnesium or zinc means. The reaction is preferably carried out in the presence of catalytic or in particular at least equimolar amounts of transition metal salts and / or compounds, in particular in the presence of Cu salts such as Cu (l) halides and especially Cu (l) iodide. As a rule, the reaction takes place in an inert organic solvent, for example an ether, in particular tetrahydrofuran, an aliphatic or cycloaliphatic hydrocarbon such as hexane, cyclohexane and the like, an aromatic hydrocarbon such as toluene or in a mixture of these solvents. The temperatures required for this are in the range of -100 to + 100 ° C and especially in the range of -80 ° C to + 40 ° C.
In analoger Weise gelingt auch die Umwandlung von Chlorverbindungen der Formel I {R1 = Cl, R2 = NR7R8}, worin R1 für d-Ce-Alkyl, d-Ce-Halogenalkyl, C2-C6-Alkenyl, C2- Ce-Alkinyl, C3-C8-Cycloalkyl oder C5-C8-Cycloalkenyl steht. Die Herstellung von Verbindungen der Formel I, worin R1 für CrC6-Alkyl, CrCe-Halogenalkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C8-Cycloalkyl oder C5-C8-Cycloalkenyl steht, gelingt beispielsweise, indem man die Chlorverbindung I {R1 = Cl und R2 = Alkyl, Cycloalkyl) in der oben beschriebenen Weise mit metallorganischen Verbindungen R1a umsetzt, worin R1a für CrC6-Alkyl, CrC6-Halogenalkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, gegebenenfalls substituiertes C3-C8-Cycloalkyl oder gegebenenfalls substituiertes C5- C8-Cycloalkenyl steht und Met für Lithium, Magnesium oder Zink steht.The conversion of chlorine compounds of the formula I {R 1 = Cl, R 2 = NR 7 R 8 }, in which R 1 is d-Ce-alkyl, d-Ce-haloalkyl, C 2 -C 6 -alkenyl, is also carried out in an analogous manner , C 2 - Ce alkynyl, C 3 -C 8 cycloalkyl or C 5 -C 8 cycloalkenyl. The preparation of compounds of the formula I in which R 1 is CrC 6 alkyl, CrCe haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl or C 5 -C 8 -Cycloalkenyl is achieved, for example, by reacting the chlorine compound I {R 1 = Cl and R 2 = alkyl, cycloalkyl) in the manner described above with organometallic compounds R 1a , where R 1a is C r C 6 -alkyl, CrC 6 Halogenoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, optionally substituted C 3 -C 8 cycloalkyl or optionally substituted C 5 - C 8 cycloalkenyl and Met stands for lithium, magnesium or zinc.
Durch entsprechende Abwandlung der in Schema 1 b gezeigten Synthese kann man in Verbindungen I mit R1 = Cl und R2 = Alkyl, Halogenalkyl, gegebenenfalls substituiertes Cycloalkyl als Substituent R1 anstelle der Gruppe NR7R8 eine Nitrilgruppe, eine Gruppe OR6' {R6' = Alkyl} oder eine Gruppe S- R6"{R6"=H oder Alkyl} nach den hier angegebenen Methoden einführen.By a corresponding modification of the synthesis shown in Scheme 1b, compounds I with R 1 = Cl and R 2 = alkyl, haloalkyl, optionally substituted cycloalkyl as substituent R 1 instead of the group NR 7 R 8 can be a nitrile group, a group OR 6 ' Introduce {R 6 ' = alkyl} or a group S- R 6 " {R 6" = H or alkyl} according to the methods given here.
Hetarylamine der allgemeinen Formel II sind teilweise käuflich, aus der Literatur bekannt oder können in Anlehnung an bekannte Verfahren aus der Literatur hergestellt werden, z. B. J. Chem. Soc. 1937, 367; J. Chem. Soc. 1953, 331 ; Bioorg. Med. Chem. 9, (2001) 2061; JACS 67, 1945, 1711.Hetarylamines of the general formula II are commercially available, known from the literature or can be prepared based on known processes from the literature, for. B. J. Chem. Soc. 1937, 367; J. Chem. Soc. 1953, 331; Bioorg. Med. Chem. 9, (2001) 2061; JACS 67, 1945, 1711.
Substituierte Phenylessigsäureester der allgemeinen Formel III sind aus der Literatur bekannt oder können in Anlehnung an bekannte Verfahren hergestellt werden.Substituted phenylacetic acid esters of the general formula III are known from the literature or can be prepared based on known processes.
Die als Edukt eingesetzten Ketone der allgemeinen Formel III stellen wertvolle Ausgangsmaterialien zur Herstellung der erfindungsgemäßen Verbindungen I {R2 =CrC6- Alkyl, CrCe-Halogenalkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C8-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, C5-C8- Cycloalkenyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist} dar.The ketones of the general formula III used as starting material are valuable starting materials for the preparation of the compounds I {R 2 = CrC 6 -alkyl, CrCe-haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 - C 8 -cycloalkyl which is optionally monosubstituted by alkyl and / or halogen or polysubstituted, C 5 -C 8 - cycloalkenyl, which is optionally monosubstituted by alkyl and / or halogen or polysubstituted} represents.
Die Ketone der allgemeinen Formel III sind neu, sofern der RestThe ketones of the general formula III are new, provided the rest
für einen Rest der Formelfor a remainder of the formula
steht, worin stands in what
Ra1 für Fluor, Chlor, Trifluormethyl oder Methyl;R a1 for fluorine, chlorine, trifluoromethyl or methyl;
Ra2 für Wasserstoff oder Fluor;R a2 for hydrogen or fluorine;
Ra3 für Wasserstoff, Fluor, Chlor, Cyano, C C4-Alkyl, speziell Methyl, C C4-Alkoxy, speziell Methoxy oder CrC4-Alkoxycarbonyl, speziell Methoxycarbonyl; Ra4 für Wasserstoff, Chlor oder Fluor; Ra5 für Wasserstoff, Fluor, Chlor oder CrC4-Alkyl, speziell Methyl, oder CrC4-Alkoxy, speziell Methoxy, stehen.R a3 for hydrogen, fluorine, chlorine, cyano, CC 4 -alkyl, especially methyl, CC 4 -alkoxy, especially methoxy or CrC 4 -alkoxycarbonyl, especially methoxycarbonyl; R a4 for hydrogen, chlorine or fluorine; R a5 is hydrogen, fluorine, chlorine or C r C 4 alkyl, especially methyl, or CrC 4 alkoxy, especially methoxy.
Gegenstand der vorliegenden Erfindung sind somit auch Ketone der allgemeinen Formel IIIDThe present invention thus also relates to ketones of the general formula IIID
worinwherein
Ra1, Ra2, Ra3, Ra4 und Ra5 die zuvor genannten Bedeutungen aufweisen undR a1 , R a2 , R a3 , R a4 and R a5 have the meanings given above and
W für CrCe-Alkyl, CrC6-Halogenalkyl, C2-C6-Alkenyl, C2-C6-Alkinyl, C3-C8- Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, C5-C8-Cycloalkenyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, steht.W is CrCe alkyl, CrC 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, which is optionally mono- or polysubstituted by alkyl and / or halogen, C 5 -C 8 cycloalkenyl, which is optionally mono- or polysubstituted with alkyl and / or halogen.
Vorzugsweise steht W' für CrC6-Alkyl, insbesondere für Methyl. Vorzugsweise ist wenigstens einer der Reste Ra3 oder Ra5 von Wasserstoff verschieden. Vorzugsweise steht wenigstens einer und besonders bevorzugt beide Reste Ra2, Ra4 für Wasserstoff.W 'is preferably CrC 6 alkyl, in particular methyl. At least one of the radicals R a3 or R a5 is preferably different from hydrogen. Preferably at least one and particularly preferably both radicals R a2 , R a4 are hydrogen.
In einer ganz besonders bevorzugten Ausführungsform der vorliegenden Erfindung steht (Ra)nfür 2-CH3-4-CI, 2-F-4-CH3, 2,6-di-F-4-CH3, 2,6-di-F-4-CN, 2,6-di-F-4- COOCH3 , 2-CF3-4-F, 2-CF3-5-F, 2-CF3-5-CI, 2-F-6-CH3, 2,6-di-F-4-OCH3, 2-CH3-4-F, 2-F-6-OCH3, 2-F-4-CI, 2-C1-4-F, 2,5-di-F, 2,4,6-tri-F oder 2,3,4-tri-F.In a very particularly preferred embodiment of the present invention, (R a ) n is 2-CH 3 -4-CI, 2-F-4-CH 3 , 2,6-di-F-4-CH 3 , 2.6 -di-F-4-CN, 2,6-di-F-4- COOCH 3 , 2-CF 3 -4-F, 2-CF 3 -5-F, 2-CF 3 -5-CI, 2 -F-6-CH 3 , 2,6-di-F-4-OCH 3 , 2-CH 3 -4-F, 2-F-6-OCH 3, 2-F-4-CI, 2-C1 -4-F, 2,5-di-F, 2,4,6-tri-F or 2,3,4-tri-F.
Die Ketone der allgemeinen Formel III, insbesondere die Ketone der allgemeinen Formel IIID, kann man beispielsweise gemäß Schema 2 herstellen, indem man einen Phenyl-ß-ketoester der allgemeinen Formel IV in Gegenwart einer schwachen wässri- gen Säure, beispielsweise Lithiumchlorid erhitzt. Schema 2:The ketones of the general formula III, in particular the ketones of the general formula IIID, can be prepared, for example, according to scheme 2 by heating a phenyl-β-keto ester of the general formula IV in the presence of a weak aqueous acid, for example lithium chloride. Scheme 2:
(IV) (III: W" = W = Alkyl, Halogenalkyl, W' = Alkyl, Halogenalkyl, Cycloalkyl, Alkenyl, Cycloalkyl, Alkenyl, Cycloalkenyl, Alkinyl) Cycloalkenyl, Alkinyl(IV) (III: W "= W = alkyl, haloalkyl, W '= alkyl, haloalkyl, cycloalkyl, alkenyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl) cycloalkenyl, alkynyl
In Schema 2 weisen Ra und n die zuvor genannten Bedeutungen, insbesondere die als bevorzugt genannten Bedeutungen auf, W' steht für CrCe-Alkyl, CrC6-Halogenalkyl, gegebenenfalls substituiertes C3-C8-Cycloalkyl, gegebenenfalls substituiertes C5-C8- Cycloalkenyl, C2-C6-Alkenyl oder C2-C6-Alkinyl. In einer bevorzugten Ausführungsform der vorliegenden Erfindung setzt man die Verbindung IV als ihren Ethylester ein.In Scheme 2, R a and n have the meanings given above, in particular the meanings mentioned as preferred, W 'stands for C r Ce alkyl, CrC 6 haloalkyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted C 5 -C 8 - cycloalkenyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl. In a preferred embodiment of the present invention, compound IV is used as its ethyl ester.
In der Regel setzt man die Säure im Uberschuss, bezogen auf den Phenyl-ß-ketoester IV, ein. Üblicherweise erhitzt man den Phenyl-ß-ketoester IV in einem Lösungsmittel. Geeignete Lösungsmittel sind dipolare aprotische Lösungsmittel wie Dimethylsulfoxid. Die Reaktionstemperatur liegt üblicherweise im Bereich von Raumtemperatur bis zum Siedepunkt des Lösungsmittel, vorzugsweise im Bereich von 60 °C bis zum Siedepunkt des Lösungsmittels. Die Phenyl-ß-ketoester IV sind entweder aus der Literatur bekannt, beispielsweise aus der WO 99/41255, oder können in Anlehnung an bekannte Verfahren aus der Literatur, beispielsweise in Anlehnung an Houben-Weyl, Band Vll/2a, S. 521 hergestellt werden.As a rule, the acid is used in excess, based on the phenyl-β-ketoester IV. The phenyl-β-ketoester IV is usually heated in a solvent. Suitable solvents are dipolar aprotic solvents such as dimethyl sulfoxide. The reaction temperature is usually in the range from room temperature to the boiling point of the solvent, preferably in the range from 60 ° C. to the boiling point of the solvent. The phenyl-β-keto esters IV are either known from the literature, for example from WO 99/41255, or can be prepared based on known processes from the literature, for example based on Houben-Weyl, volume Vll / 2a, p. 521 become.
Die Verbindungen I eignen sich als Fungizide. Sie zeichnen sich aus durch eine hervorragende Wirksamkeit gegen ein breites Spektrum von pflanzenpathogenen Pilzen, insbesondere aus der Klasse der Ascomyceten, Deuteromyceten, Oomyceten und Ba- sidiomyceten. Sie sind zum Teil systemisch wirksam und können im Pflanzenschutz als Blatt- und Bodenfungizide eingesetzt werden.The compounds I are suitable as fungicides. They are characterized by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides.
Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Weizen, Roggen, Gerste, Hafer, Reis, Mais, Gras, Bananen, Baumwolle, Soja, Kaffee, Zuckerrohr, Wein, Obst- und Zierpflanzen und Gemüsepflanzen wie Gurken, Bohnen, Tomaten, Kartoffeln und Kürbisgewächsen, sowie an den Samen dieser Pflanzen. Speziell eignen sie sich zur Bekämpfung folgender Pflanzenkrankheiten: Altemaria-Aύen an Gemüse und Obst, Bipolaris- und DrecΛs/era-Arten an Getreide, Reis und Rasen, Blumeria graminis (echter Mehltau) an Getreide, - Botrytis cinerea (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben, Erysiphθ cichoracearum und Sphaerotheca fuliginea an Kürbisgewächsen, Fusarium- und Verticillium-Arten an verschiedenen Pflanzen, Mycosphaerella-Men an Getreide, Bananen und Erdnüssen, - Phytophthora infestans an Kartoffeln und Tomaten, Plasmopara viticola an Reben, Podosphaera leucotricha an Äpfeln, Pseudocercosporella herpotrichoides an Weizen und Gerste, Pseudoperonospora-Arten an Hopfen und Gurken, - Puccinia-AΛen an Getreide, Pyricularia oryzae an Reis, Rhizoctonia-Aήen an Baumwolle, Reis und Rasen, Rhynchosporium secalis (Blattfleckenkrankheit) an Getreide Septoria tritici und Stagonospora nodorum an Weizen, - Uncinula necator an Reben, Us./.ago-Arten an Getreide und Zuckerrohr, sowie Ven.i/r/a-Arten (Schorf) an Äpfeln und Birnen.They are particularly important for combating a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soybeans, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers, Beans, tomatoes, potatoes and squash, as well as on the seeds of these plants. They are particularly suitable for combating the following plant diseases: Altemaria plants on vegetables and fruits, Bipolaris and DrecΛs / era species on cereals, rice and turf, Blumeria graminis (powdery mildew) on cereals, - Botrytis cinerea (gray mold) on strawberries, Vegetables, ornamental plants and vines, Erysiphθ cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Fusarium and Verticillium species on various plants, Mycosphaerella-Men on cereals, bananas and peanuts, - Phytophthora infestans on potatoes and tomatoes, Plasmopara vitica anera on vines, Podopara viticola on vines Apples, Pseudocercosporella herpotrichoides on wheat and barley, Pseudoperonospora species on hops and cucumbers, - Puccinia-AΛen on cereals, Pyricularia oryzae on rice, Rhizoctonia-Aήen on cotton, rice and turf, Rhynchosporium secalis (leaf spot disease and Stagonagonitisi) on cereals Septoriapori nodorum on wheat, - Uncinula necator on vines, Us./.ago species on cereals and sugar cane, and Ven.i / r / a species (scab) on apples and pears.
Die Verbindungen I eignen sich außerdem zur Bekämpfung von Schadpilzen wie Pae- cilomyces variotii im Materialschutz (z.B. Holz, Papier, Dispersionen für den Anstrich, Fasern bzw. Gewebe) und im Vorratsschutz.The compounds I are also suitable for combating harmful fungi such as Pacilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
Die Verbindungen I werden angewendet, indem man die Pilze oder die vor Pilzbefall zu schützenden Pflanzen, Saatgüter, Materialien oder den Erdboden mit einer fungizid wirksamen Menge der Wirkstoffe behandelt. Die Anwendung kann sowohl vor als auch nach der Infektion der Materialien, Pflanzen oder Samen durch die Pilze erfolgen.The compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds. The application can take place both before and after the infection of the materials, plants or seeds by the fungi.
Die fungiziden Mittel enthalten im Allgemeinen zwischen 0,1 und 95, vorzugsweise zwischen 0,5 und 90 Gew.-% Wirkstoff.The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
Die Aufwandmengen liegen bei der Anwendung im Pflanzenschutz je nach Art des gewünschten Effektes zwischen 0,01 und 2,0 kg Wirkstoff pro ha.Depending on the type of effect desired, the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
Bei der Saatgutbehandlung werden im allgemeinen Wirkstoffmengen von 0,001 bis 1 g, vorzugsweise 0,01 bis 0,5 g je Kilogramm Saatgut benötigt. Bei der Anwendung im Material- bzw. Vorratsschutz richtet sich die Aufwandmenge an Wirkstoff nach der Art des Einsatzgebietes und des gewünschten Effekts. Übliche Aufwandmengen sind im Materialschutz beispielsweise 0,001 g bis 2 kg, vorzugsweise 0,005 g bis 1 kg Wirkstoff pro Kubikmeter behandelten Materials.In the case of seed treatment, amounts of active ingredient of 0.001 to 1 g, preferably 0.01 to 0.5 g, are generally required per kilogram of seed. When used in material or stock protection, the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.
Die Verbindungen I können in die üblichen Formulierungen überführt werden, z.B. Lösungen, Emulsionen, Suspensionen, Stäube, Pulver, Pasten und Granulate. Die Anwendungsform richtet sich nach dem jeweiligen Verwendungszweck; sie soll in jedem Fall eine feine und gleichmäßige Verteilung der erfindungsgemäßen Verbindung gewährleisten.The compounds I can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules. The form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compound according to the invention.
Die Formulierungen werden in bekannter Weise hergestellt, z.B. durch Verstrecken des Wirkstoffs mit Lösungsmitteln und/oder Trägerstoffen, gewünschtenfalls unter Verwen- düng von Emulgiermitteln und Dispergiermitteln, wobei im Falle von Wasser als Verdünnungsmittel auch andere organische Lösungsmittel als Hilfslösungsmittel verwendet werden können. Als Hilfsstoffe kommen dafür im wesentlichen in Betracht: Lösungsmittel wie Aromaten (z.B. Xylol), chlorierte Aromaten (z.B. Chlorbenzole), Paraffine (z.B. Erdölfraktionen), Alkohole (z.B. Methanol, Butanol), Ketone (z.B. Cyclohexa- non), Amine (z.B. Ethanolamin, Dimethylformamid) und Wasser; Trägerstoffe wie natürliche Gesteinsmehle (z.B. Kaoline, Tonerden, Talkum, Kreide) und synthetische Gesteinsmehle (z.B. hochdisperse Kieselsäure, Silikate); Emulgiermittel wie nichtionoge- ne und anionische Emulgatoren (z.B. Polyoxyethylen-Fettalkohol-Ether, Alkylsulfonate und Arylsulfonate) und Dispergiermittel wie Lignin-Sulfitablaugen und Methylcellulose.The formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, where, in the case of water as the diluent, other organic solvents can also be used as auxiliary solvents. The following are essentially considered as auxiliaries: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine , Dimethylformamide) and water; Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
Als oberflächenaktive Stoffe kommen Alkali-, Erdalkali-, Ammoniumsalze von Ligninsul- fonsäure, Naphthalinsulfonsäure, Phenolsulfonsäure, Dibutylnaphthalinsulfonsäure, Alkylarylsulfonate, Alkylsulfate, Alkylsulfonate, Fettalkoholsulfate und Fettsäuren sowie deren Alkali- und Erdalkalisalze, Salze von sulfatiertem Fettalkoholglykolether, Kon- densationsprodukte von sulfoniertem Naphthalin und Naphthalinderivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphtalinsulfonsäure mit Phenol und Formaldehyd, Polyoxyethylenoctylphenolether, ethoxyliertes Isooctylphe- nol, Octylphenol, Nonylphenol, Alkylphenolpolyglykolether, Tributylphenylpolyglykol- ether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylenoxid-Konden- säte, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether, ethoxyliertes Polyoxypropylen, Laurylalkoholpolyglykoletheracetal, Sorbitester, Ligninsulfitablaugen und Methylcellulose in Betracht.Alkali, alkaline earth, ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates and fatty acids as well as their alkali and alkaline earth metal salts and alkali metal sulfonate salts, salts of sulfonated sulfonated ether, salts of sulfonated sulfonated ether and salts of sulfonated sulfonated fatty acid Naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenylpolyglycol ether, alkylaryl polyotyl ethoxylated alcoholoethylene, ethoxylated alcohol, ethoxylated alcohol, ethoxylated alcohol , Laurylalkolypolyglykoletheracetal, sorbitol esters, lignin sulfite liquors and methyl cellulose.
Zur Herstellung von direkt versprühbaren Lösungen, Emulsionen, Pasten oder Öldis- persionen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kero- sin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Benzol, Toluol, Xylol, Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, Methanol, Ethanol, Propanol, Butanol, Chloroform, Tetrachlorkohlenstoff, Cyclohe- xanol, Cyclohexanon, Chlorbenzol, Isophoron, stark polare Lösungsmittel, z.B. Di- methylformamid, Dimethylsulfoxid, N-Methylpyrrolidon, Wasser, in Betracht.Mineral oil fractions of medium to high boiling point, such as kerosene, are used to produce directly sprayable solutions, emulsions, pastes or oil dispersions. sin or diesel oil, also coal tar oils as well as oils of plant or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohe - xanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, for example dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, into consideration.
Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate, können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind z.B. Mineralerden, wie Kieselgele, Silikate, Talkum, Kaolin, Attaclay, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsul- fat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie z.B. Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte, wie Ge- treidemehl, Baumrinden-, Holz- und Nussschalenmehl, Cellulosepulver und andere feste Trägerstoffe.Granules, e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers. Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as grain flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
Die Formulierungen enthalten im Allgemeinen zwischen 0,01 und 95 Gew.-%, vorzugsweise zwischen 0,1 und 90 Gew.-% des Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR-Spektrum) eingesetzt.The formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight of the active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
Beispiele für Formulierungen sind:Examples of formulations are:
I. 5 Gew.-Teile einer erfindungsgemäßen Verbindung werden mit 95 Gew.-Teilen feinteiligem Kaolin innig vermischt. Man erhält auf diese Weise ein Stäubemittel, das 5 Gew.-% des Wirkstoffs enthält.I. 5 parts by weight of a compound according to the invention are intimately mixed with 95 parts by weight of finely divided kaolin. In this way a dust is obtained which contains 5% by weight of the active ingredient.
II. 30 Gew.-Teile einer erfindungsgemäßen Verbindung werden mit einer Mischung aus 92 Gew.-Teilen pulverförmigem Kieselsäuregel und 8 Gew.-Teilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels gesprüht wurde, innig vermischt. Man erhält auf diese Weise eine Aufbereitung des Wirkstoffs mit guter Haftfähig- keit (Wirkstoffgehalt 23 Gew.-%).II. 30 parts by weight of a compound according to the invention are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. In this way a preparation of the active ingredient with good adhesion (active ingredient content 23% by weight) is obtained.
III. 10 Gew.-Teile einer erfindungsgemäßen Verbindung werden in einer Mischung gelöst, die aus 90 Gew.-Teilen Xylol, 6 Gew.-Teilen des Anlagerungsproduktes von 8 bis 10 Mol Ethylenoxid an 1 Mol Ölsäure-N-monoethanolamid, 2 Gew.- Teilen Calciumsalz der Dodecylbenzolsulfonsäure und 2 Gew.-Teilen des Anla- gerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht (Wirkstoffgehalt 9 Gew.-%).III. 10 parts by weight of a compound according to the invention are dissolved in a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 2 parts by weight Calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the plant tion product of 40 moles of ethylene oxide with 1 mole of castor oil (active ingredient content 9% by weight).
IV. 20 Gew.-Teile einer erfindungsgemäßen Verbindung werden in einer Mischung gelöst, die aus 60 Gew.-Teilen Cyclohexanon, 30 Gew.-Teilen Isobutanol, 5 Gew.-Teilen des Anlagerungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooc- tylphenol und 5Gew.-Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht (Wirkstoffgehalt 16 Gew.-%).IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture consisting of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of iso-octylphenol and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil (active ingredient content 16% by weight).
V. 80 Gew.-Teile einer erfindungsgemäßen Verbindung werden mit 3 Gew.-Teilen des Natriumsalzes der Diisobutylnaphthalin-α-sulfonsäure, 10 Gew.-Teilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 7 Gew.- Teilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen (Wirkstoffgehalt 80 Gew.-%).V. 80 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and grind in a hammer mill (active ingredient content 80% by weight).
VI. Man vermischt 90 Gew.-Teile einer erfindungsgemäßen Verbindung mit 10 Gew.- Teilen N-Methyl-α-pyrrolidon und erhält eine Lösung, die zur Anwendung in Form kleinster Tropfen geeignet ist (Wirkstoffgehalt 90 Gew.-%).VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-α-pyrrolidone and a solution is obtained which is suitable for use in the form of very small drops (active substance content 90% by weight).
VII. 20 Gew.-Teile einer erfindungsgemäßen Verbindung werden in einer Mischung gelöst, die aus 40 Gew.-Teilen Cyclohexanon, 30 Gew.-Teilen Isobutanol, 20 Gew.-Teilen des Anlagerungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooctylphenol und 10 Gew.-Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lö- sung in 100 000 Gew.-Teilen Wasser erhält man eine wässrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält.VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 10 parts by weight . Parts of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.
VIII. 20 Gew.-Teile einer erfindungsgemäßen Verbindung werden mit 3 Gew.-Teilen des Natriumsalzes der Diisobutylnaphthalin-α-sulfonsäure, 17 Gew.-Teilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gew.- Teilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen. Durch feines Verteilen der Mischung in 20000 Gew.-Teilen Wasser erhält man eine Spritzbrühe, die 0,1 Gew.-% des Wirkstoffs enthält.VIII. 20 parts by weight of a compound according to the invention are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and milled in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, z.B. in Form von direkt versprühbaren Lösungen, Pulvern, Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln, Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsformen richten sich ganz nach den Ver- Wendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The active ingredients as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or Pouring can be applied. The application forms depend entirely on the Twist purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Wässrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netz- baren Pulvern (Spritzpulver, Oldispersionen) durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Oldispersionen können die Substanzen als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermitttel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz Netz-, Haft-, Dispergier- oder Emulgiermittel und even- tuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, old dispersions) by adding water. To prepare emulsions, pastes or old dispersions, the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates composed of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
Die Wirkstoffkonzentrationen in den anwendungsfertigen Zubereitungen können in größeren Bereichen variiert werden. Im allgemeinen liegen sie zwischen 0,0001 und 10%, vorzugsweise zwischen 0,01 und 1%.The active ingredient concentrations in the ready-to-use preparations can be varied over a wide range. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
Die Wirkstoffe können auch mit gutem Erfolg im Ultra-Low-Volume-Verfahren (ULV) verwendet werden, wobei es möglich ist, Formulierungen mit mehr als 95 Gew.-% Wirkstoff oder sogar den Wirkstoff ohne Zusätze auszubringen.The active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
Zu den Wirkstoffen können Öle verschiedenen Typs, Herbizide, Fungizide, andere Schädlingsbekämpfungsmittel, Bakterizide, gegebenenfalls auch erst unmittelbar vor der Anwendung (Tankmix), zugesetzt werden. Diese Mittel können zu den erfindungsgemäßen Mitteln im Gewichtsverhältnis 1:10 bis 10:1 zugemischt werden.Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
Die erfindungsgemäßen Mittel können in der Anwendungsform als Fungizide auch zusammen mit anderen Wirkstoffen vorliegen, der z.B. mit Herbiziden, Insektiziden, Wachstumsregulatoren, Fungiziden oder auch mit Düngemitteln. Beim Vermischen der Verbindungen I bzw. der sie enthaltenden Mittel in der Anwendungsform als Fungizide mit anderen Fungiziden erhält man in vielen Fällen eine Vergrößerung des fungiziden Wirkungsspektrums.In the use form as fungicides, the compositions according to the invention can also be present together with other active compounds which, e.g. with herbicides, insecticides, growth regulators, fungicides or also with fertilizers. Mixing the compounds I or the compositions containing them in the use form as fungicides with other fungicides results in an enlargement of the fungicidal spectrum of action in many cases.
Die folgende Liste von Fungiziden, mit denen die erfindungsgemäßen Verbindungen gemeinsam angewendet werden können, soll die Kombinationsmöglichkeiten erläutern, nicht aber einschränken:The following list of fungicides with which the compounds according to the invention can be used together is intended to explain, but not to limit, the possible combinations:
• Acylalanine wie Benalaxyl, Metalaxyl, Ofurace, Oxadixyl,Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,
• Aminderivate wie Aldimorph, Dodine, Dodemorph, Fenpropimorph, Fenpropidin, Guazatine, Iminoctadine, Spiroxamin, Tridemorph, • Anilinopyrimidine wie Pyrimethanil, Mepanipyrim oder Cyrodinyl,Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine, tridemorph, Anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl,
• Antibiotika wie Cycioheximid, Griseofulvin, Kasugamycin, Natamycin, Polyoxin oder Streptomycin,Antibiotics such as cycioheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,
• Azole wie Bitertanol, Bromoconazol, Cyproconazol, Difenoconazole, Dinitroco- nazol, Epoxiconazol, Fenbuconazol, Fluquiconazol, Flusilazol, Hexaconazol, I- mazalil, Metconazol, Myclobutanil, Penconazol, Propiconazol, Prochloraz, Prothioconazol, Tebuconazol, Triadimefon, Triadimenol, Triflumizol, Triticonazol,• azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, Dinitroco- Nazole, epoxiconazole, fenbuconazole, Fluquiconazol, flusilazole, hexaconazole, I mazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, triadimefon, triadimenol, triflumizole, triticonazole .
• Dicarboximide wie Iprodion, Myclozolin, Procymidon, Vinclozolin,Dicarboximides such as iprodione, myclozolin, procymidone, vinclozolin,
• Dithiocarbamate wie Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Pro- pineb, Polycarbamat, Thiram, Ziram, Zineb,Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propinerb, Polycarbamat, Thiram, Ziram, Zineb,
• Heterocylische Verbindungen wie Anilazin, Benomyl, Boscalid, Carbendazim, Carboxin, Oxycarboxin, Cyazofamid, Dazomet, Dithianon, Famoxadon, Fenami- don, Fenarimol, Fuberidazol, Flutolanil, Furametpyr, Isoprothiolan, Mepronil, Nu- arimol, Probenazol, Proquinazid, Pyrifenox, Pyroquilon, Quinoxyfen, Silthiofam, Thiabendazol, Thifluzamid, Thiophanat-methyl, Tiadinil, Tricyclazol, Triforine,• Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, Dazomet, dithianon, famoxadone, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolan, mepronquin, probolene, probuene, nu- arifonil, probu- Pyroquilon, Quinoxyfen, Silthiofam, Thiabendazol, Thifluzamid, Thiophanat-methyl, Tiadinil, Tricyclazol, Triforine,
• Kupferfungizide wie Bordeaux Brühe, Kupferacetat, Kupferoxychlorid, basisches Kupfersulfat,Copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate,
• Nitrophenylderivate, wie Binapacryl, Dinocap, Dinobuton, Nitrophthal-isopropyl,Nitrophenyl derivatives, such as binapacryl, dinocap, dinobutone, nitrophthal-isopropyl,
• Phenylpyrrole wie Fenpiclonil oder Fludioxonil, • Schwefel,Phenylpyrroles such as fenpiclonil or fludioxonil, sulfur,
• Sonstige Fungizide wie Acibenzolar-S-methyl, Benthiavalicarb, Carpropamid, Chlorothalonil, Cyflufenamid, Cymoxanil, Dazomet, Diclomezin, Diclocymet, Diethofencarb, Edifenphos, Ethaboxam, Fenhexamid, Fentin-Acetat, Fenoxanil, Ferimzone, Fluazinam, Fosetyl, Fosetyl-Aluminium, Iprovalicarb, Hexachlorben- zol, Metrafenon, Pencycuron, Propamocarb, Phthalid, Toloclofos-methyl, Quinto- zene, Zoxamid,Other fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chlorothalonil, cyflufenamid, cymoxanil, Dazomet, diclomezin, diclocymet, diethofencarb, edifenphos, ethaboxam, fenhexamide, fentin acetate, fenoxanil, fosetylamino, fefosetone, ferimosone, ferimzone Iprovalicarb, hexachlorobenzene, metrafenone, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintocene, zoxamide,
• Strobilurine wie Azoxystrobin, Dimoxystrobin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin oder Trifloxystro- bin, • Sulfensäurederivate wie Captafol, Captan, Dichlofluanid, Folpet, Tolylfluanid,• Strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin, • Sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid,
• Zimtsäureamide und Analoge wie Dimethomorph, Flumetover oder Flumorph.• Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
Synthesebeispielesynthesis Examples
Die in den nachstehenden Synthesebeispielen wiedergegebenen Vorschriften wurden unter entsprechender Abwandlung der Ausgangsverbindungen zur Gewinnung weiterer Verbindungen I benutzt. Die so erhaltenen Verbindungen sind in den anschließenden Tabellen mit physikalischen Angaben aufgeführt. Vorstufenbeispiel 1 :The instructions given in the synthesis examples below were used with the appropriate modification of the starting compounds to obtain further compounds I. The compounds thus obtained are listed in the tables below with physical details. Prepress example 1:
1-(2,4,6-Trifluorphenyl)propan-2-on1- (2,4,6-trifluorophenyl) propan-2-one
Zu 15 g (0,052 mol) 3-Oxo-2-(2,4,6-trifluorphenyll)butansäureethylester in 100 ml Di- methylsulfoxid gab man portionsweise 42,4 g (0,103 mol) Lithiumchlorid. Danach tropfte man 18 g (0,052 mol) Wasser zu und rührte das erhaltene Reaktionsgemisch 6,5 Stunden bei 110 °C. Man ließ das Reaktionsgemisch abkühlen, gab 50 ml Wasser zu und extrahierte das wässrige Reaktionsgemisch mehrmals mit Cyclohexan. Die vereinigten organischen Phasen trocknete man, filtrierte danach das Trockenmittel ab und engte das Filtrat ein. Den erhaltenen Rückstand chromatographierte man an Kieselgel (Cyclohexan/Essigsäureethylester 99:1), wobei man nach dem Einengen 4,5 g (46 %) der Titelverbindung erhielt.42.4 g (0.103 mol) of lithium chloride were added in portions to 15 g (0.052 mol) of ethyl 3-oxo-2- (2,4,6-trifluorophenyl) butanoate in 100 ml of dimethyl sulfoxide. Then 18 g (0.052 mol) of water were added dropwise and the reaction mixture obtained was stirred at 110 ° C. for 6.5 hours. The reaction mixture was allowed to cool, 50 ml of water were added and the aqueous reaction mixture was extracted several times with cyclohexane. The combined organic phases were dried, then the drying agent was filtered off and the filtrate was concentrated. The residue obtained was chromatographed on silica gel (cyclohexane / ethyl acetate 99: 1), giving 4.5 g (46%) of the title compound after concentration.
In analoger Weise können die in der nachfolgenden Tabelle 1 angegebenen Verbindungen III erhalten werden:The compounds III given in Table 1 below can be obtained in an analogous manner:
Tabelle 1:Table 1:
Beispiel 1: Example 1:
6-(2,4,6-Trifluorphenyl)pyrido[2,3-d]pyrimidin-5,7-diol6- (2,4,6-trifluorophenyl) pyrido [2,3-d] pyrimidine-5,7-diol
Zu 6,7 g (0,033 mol) 2,4,6-Trifluorphenylessigsäureethylester gab man bei Raumtemperatur 2,44 g (0,036 mol) Natriumethanolat und rührte etwa 5 Minuten nach. Danach gab man 3 g (0,018 mol) 4-Aminopyrimidin-5-carbonsäureethylester zu und erhitzte die erhaltene Suspension auf 130 °C. Um die Suspension besser rühren zu können, gab man weitere 8 ml 2,4,6-Trifluorphenylessigsäureethylester zu. Man erhitzte die Sus- pension 6 Stunden und destillierte das gebildete Ethanol ab. Danach ließ man abkühlen und goss das Reaktionsgemisch auf Wasser. Das wässrige Reaktionsgemisch extrahierte man mit Essigsäureethylester. Die organische Schicht trocknete man, filtrierte das Trockenmittel ab und engte bis zur Trockne ein, wobei man 8,6 g 2,4,6-Trifluor- phenylessigsäureethylester zurückgewann. Die wässrige Phase stellte man mit Essig- säure auf einen pH-Wert von 5,5, wobei ein Feststoff ausfiel. Der ausgefallene Feststoff wurde abfiltriert und getrocknet, wobei man 1,6 g (30 %) der Titelverbindung erhielt.2.44 g (0.036 mol) of sodium ethanolate were added to 6.7 g (0.033 mol) of 2,4,6-trifluorophenylacetic acid at room temperature and the mixture was stirred for about 5 minutes. Then 3 g (0.018 mol) of 4-aminopyrimidine-5-carboxylic acid ethyl ester were added and the suspension obtained was heated to 130.degree. In order to be able to stir the suspension better, a further 8 ml of ethyl 2,4,6-trifluorophenylacetate were added. The suspension was heated for 6 hours and the ethanol formed was distilled off. The mixture was then allowed to cool and the reaction mixture was poured onto water. The aqueous reaction mixture was extracted with ethyl acetate. The organic layer was dried, the drying agent was filtered off and the mixture was evaporated to dryness, 8.6 g of ethyl 2,4,6-trifluorophenylacetate being recovered. The aqueous phase was adjusted to pH 5.5 with acetic acid, a solid precipitating out. The precipitated solid was filtered off and dried to give 1.6 g (30%) of the title compound.
Beispiel 2:Example 2:
5,7-Dichlor-6-(2,4,6-trifluorphenyl)pyrido[2,3-d]pyrimidin5,7-dichloro-6- (2,4,6-trifluorophenyl) pyrido [2,3-d] pyrimidine
Zu 4,2 g (0,014 mol) 6-(2,4,6-Trifluorphenyl)pyrido[2,3-d]pyrimidin-5,7-diol aus Beispiel 1 in 40 ml Phosphoroxychlorid gab man unter Rühren 7,74 g (0,037 mol) Phosphorpen- tachlorid und erwärmte unter Rühren 8 Stunden auf 130 °C. Nach dem Abkühlen engte man das Reaktionsgemisch ein und nahm den Rückstand in Dichlormethan auf. Danach gab man vorsichtig 150 ml Wasser zu und stellte das wässrige Reaktionsgemisch mit Natriumcarbonat-Lösung alkalisch. Die organische Phase trennte man ab, extrahierte die wässrige Phase zweimal mit Dichlormethan und trocknete die vereinigten organischen Phasen. Nach dem Abfiltrieren des Trockenmittels und Einengen der organischen Phase erhielt man 4,4 g (95 %) der Titelverbindung.To 4.2 g (0.014 mol) of 6- (2,4,6-trifluorophenyl) pyrido [2,3-d] pyrimidine-5,7-diol from Example 1 in 40 ml of phosphorus oxychloride was added 7.74 g with stirring (0.037 mol) of phosphorus pentachloride and heated to 130 ° C. with stirring for 8 hours. After cooling, the reaction mixture was concentrated and the residue was taken up in dichloromethane. Then 150 ml of water were carefully added and the aqueous reaction mixture was made alkaline with sodium carbonate solution. The organic phase was separated off, the aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried. After filtering off the drying agent and concentrating the organic phase, 4.4 g (95%) of the title compound were obtained.
Beispiel 3:Example 3:
7-Benzyloxy-5-chlor-6-(2,4,6-trifluorphenyl)pyrido[2,3-d]pyrimidin7-benzyloxy-5-chloro-6- (2,4,6-trifluorophenyl) pyrido [2,3-d] pyrimidine
Zu 0,29 g (0,0073 mol) 60%igem Natriumhydrid in Weißöl tropfte man vorsichtig unter Kühlen 10 ml Benzylalkohol und rührte 30 Minuten bei Raumtemperatur nach. Danach gab man vorsichtig 2,4 g (0,0073 mol) 5,7-Dichlor-6-(2,4,6-trifluorphenyl)pyrido[2,3- d]pyrimidin aus Beispiel 2 zu und ließ etwa 100 Stunden bei Raumtemperatur stehen. Man gab das Reaktionsgemisch auf Wasser und extrahierte dreimal mit Essigsäure- ethylester und trocknete die vereinigten organischen Phasen. Nach dem Abfiltrieren des Trockenmittels und Einengen der organischen Phase erhielt man 3 g (100 %) der Titelverbindung, die geringfügig verunreinigt war.10 ml of benzyl alcohol were carefully added dropwise to 0.29 g (0.0073 mol) of 60% sodium hydride in white oil and the mixture was stirred at room temperature for 30 minutes. Thereafter, 2.4 g (0.0073 mol) of 5,7-dichloro-6- (2,4,6-trifluorophenyl) pyrido [2,3-d] pyrimidine from Example 2 were carefully added and the mixture was left in for about 100 hours Stand at room temperature. The reaction mixture was poured into water and extracted three times with ethyl acetate and the combined organic phases were dried. After filtering off the drying agent and concentrating the organic phase, 3 g (100%) of the title compound were obtained, which was slightly contaminated.
Beispiel 4:Example 4:
5-Chlor-7-(4-methylpiperidinyl)-6-(2,4,6-trifluorphenyl)pyrido[2,3-d]pyrimidin5-chloro-7- (4-methylpiperidinyl) -6- (2,4,6-trifluorophenyl) pyrido [2,3-d] pyrimidine
Man löste 0,1 g (0,3 mmol) 5,7-Dichlor-6-(2,4,6-trifluorphenyl)pyrido[2,3-d]pyrimidin aus Beispiel 2 in 1 ml Dichlormethan und 0,04 ml Triethylamin. Danach gab man 0,03 g (3 mmol) 4-Methylpiperidin zu und rührte 12 Stunden bei Raumtemperatur. Das Reaktionsgemisch nahm man in wenig Wasser und Dichlormethan auf und wusch die organische Phase mit verdünnter wässriger Salzsäure. Nach dem Trocknen der organischen Phase filtrierte man das Trockenmittel ab und engte das Filtrat bis zur Trockne ein, wobei man 0,1 g (85 %) der Titelverbindung erhielt.0.1 g (0.3 mmol) of 5,7-dichloro-6- (2,4,6-trifluorophenyl) pyrido [2,3-d] pyrimidine from Example 2 was dissolved in 1 ml of dichloromethane and 0.04 ml triethylamine. Then 0.03 g (3 mmol) of 4-methylpiperidine was added and the mixture was stirred at room temperature for 12 hours. The reaction mixture was taken up in a little water and dichloromethane and the organic phase was washed with dilute aqueous hydrochloric acid. After drying the organic phase, the drying agent was filtered off and the filtrate was evaporated to dryness, giving 0.1 g (85%) of the title compound.
Beispiel 5:Example 5:
2,7-Dimethyl-3-(2,4,6-trifluorphenyl)-[1,8]naphthyridin-4-ol2,7-dimethyl-3- (2,4,6-trifluorophenyl) - [1,8] naphthyridin-4-ol
Man gab 1 ,3 g (0,0072 mol) 2-Amino-6-methylnicotinsäureethylester und 1 ,48 g (0,0079 mol) 1-(2,4,6-Trifluorphenyl)-propan-2-on aus Vorstufenbeispiel 1 portionsweise und abwechselnd bei 120 °C zu 5 g Polyphosphorsäure und erhitzte nach beende- ter Zugabe noch 5 Stunden auf 150 °C. Man ließ das Reaktionsgemisch abkühlen, gab danach etwa 60 ml Eiswasser zu und stellte mit 4 N Natriumhydroxid-Lösung auf pH 7, wobei ein Niederschlag ausfiel. Den Niederschlag filtrierte man ab und trocknete ihn, wobei man 0,56 g der Titelverbindung erhielt.1.3 g (0.0072 mol) of 2-amino-6-methylnicotinic acid ethyl ester and 1.48 g (0.0079 mol) of 1- (2,4,6-trifluorophenyl) propan-2-one from precursor example 1 were added in portions and alternately at 120 ° C. to 5 g of polyphosphoric acid and, after the addition has ended, heated to 150 ° C. for 5 hours. The reaction mixture was allowed to cool, then about 60 ml of ice water was added and the pH was adjusted to 7 with 4N sodium hydroxide solution, during which a precipitate separated out. The precipitate was filtered off and dried to give 0.56 g of the title compound.
Beispiel 6:Example 6:
4-Chlor-2,7-dimethyl-3-(2,4,6-trifluorphenyl)-[1,8]naphthyridin4-chloro-2,7-dimethyl-3- (2,4,6-trifluorophenyl) - [1,8] naphthyridin
Zu 0,165 g (0,54 mmol) 2,7-Dimethyl-3-(2,4,6-trifluorphenyl)-[1,8]naphthyridin-4-ol aus Beispiel 5 in 1,26 ml Phosphoroxychlorid gab man 0,147 g (0,7 mmol) Phosphorpen- tachlorid. Das erhaltene Reaktionsgemisch rührte man 3 Stunden bei 110 °C, ließ danach abkühlen, gab Eiswasser zu und stellte mit wässriger Natriumcarbonat-Lösung alkalisch. Das wässrige Reaktionsgemisch extrahierte man viermal mit Dichlormethan, trocknete die vereinigten organischen Phasen, filtrierte das Trockenmittel ab und engte ein, wobei man 0,18 g der Titelverbindung erhielt. Beispiel 7:0.147 g was added to 0.165 g (0.54 mmol) of 2,7-dimethyl-3- (2,4,6-trifluorophenyl) - [1,8] naphthyridin-4-ol from Example 5 in 1.26 ml of phosphorus oxychloride (0.7 mmol) phosphorus pentachloride. The reaction mixture obtained was stirred at 110 ° C. for 3 hours, then allowed to cool, ice water was added and the mixture was made alkaline with aqueous sodium carbonate solution. The aqueous reaction mixture was extracted four times with dichloromethane, the combined organic phases were dried, the drying agent was filtered off and the mixture was concentrated to give 0.18 g of the title compound. Example 7:
7-Benzyloxy-5-(4-methylpiperidinyl)-6-(2,4,6-trifluorphenyl)pyrido[2,3-d]pyrimidin und 5- Chlor-6-(2,4,6-trifluorphenyl)pyrido[2,3-d]pyrimidin-7-ol7-benzyloxy-5- (4-methylpiperidinyl) -6- (2,4,6-trifluorophenyl) pyrido [2,3-d] pyrimidine and 5-chloro-6- (2,4,6-trifluorophenyl) pyrido [ 2,3-d] pyrimidin-7-ol
Man rührte das Reaktionsgemisch aus 0,12 g (0,3 mmol) 7-Benzyloxy-5-chlor-6-(2,4,6- trifluorphenyl)pyrido[2,3-d]pyrimidin aus Beispiel 3, 1,5 g 4-Methylpiperidin und 0,05 g Triethylamin 3 Stunden bei 80 °C. Das Reaktionsgemisch nahm man in Wasser auf und wusch das wässrige Gemisch dreimal mit Dichlormethan. Nach dem Trocknen der vereinigten organischen Phasen filtrierte man das Trockenmittel ab und engte das Filt- rat ein. Den Rückstand chromatographierte an Kieselgel mit Cyclohexan:Essigsäure- ethylester (95:5), wobei man 0,06 g eines Gemisches aus der Titelverbindung und 5- Chlor-6-(214,6-trifluorphenyl)pyrido[2,3-d]pyrimidin-7-ol erhielt.The reaction mixture was stirred from 0.12 g (0.3 mmol) of 7-benzyloxy-5-chloro-6- (2,4,6-trifluorophenyl) pyrido [2,3-d] pyrimidine from Example 3, 1.5 g of 4-methylpiperidine and 0.05 g of triethylamine for 3 hours at 80 ° C. The reaction mixture was taken up in water and the aqueous mixture was washed three times with dichloromethane. After the combined organic phases had dried, the drying agent was filtered off and the filtrate was concentrated. The residue was chromatographed on silica gel using cyclohexane: ethyl acetate (95: 5), 0.06 g of a mixture of the title compound and 5-chloro-6- (2 1 4,6-trifluorophenyl) pyrido [2,3- d] pyrimidin-7-ol was obtained.
Beispiel 8:Example 8:
5-(4-Methylpiperidin-1-yl)-6-(2,4,6-trifluorphenyl)pyrido[2,3-d]pyrimidin-7-ol5- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) pyrido [2,3-d] pyrimidin-7-ol
In einer Laborhydrierapparatur mit Begasungsrührer (2000 min"1) legte man 0,6 g (0,0013 mol) 7-Benzyloxy-5-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorphenyl)pyrido[2,3- d]pyrimidin (80 %ig) aus Beispiel 7 in 20 ml Methanol vor. Anschließend gab man 0,03 g Pd/C (10%ig) zu und hydrierte bis zur maximalern Wasserstoffaufnahme. Bei einer Temperatur von 30 °C hydrierte man etwa 90 min. Danach saugte man das Gemisch über Kieselgur ab und engte den erhaltenen Rückstand unter vermindertem Druck ein. Nach säulenchromatographischer Reinigung erhielt man 0,25 g (52 %) der Titelverbindung.0.6 g (0.0013 mol) of 7-benzyloxy-5- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) was placed in a laboratory hydrogenation apparatus with a gassing stirrer (2000 min "1 ). pyrido [2,3-d] pyrimidine (80% strength) from Example 7 in 20 ml of methanol, then 0.03 g of Pd / C (10% strength) were added and the mixture was hydrogenated to the maximum hydrogen uptake at a temperature of The mixture was hydrogenated for about 90 minutes at 30 ° C. The mixture was then suction filtered through diatomaceous earth and the residue obtained was concentrated under reduced pressure, after purification by column chromatography, 0.25 g (52%) of the title compound was obtained.
Beispiel 9:Example 9:
7-Chlor-5-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluormphenyl)pyrido[2,3-d]pyrimidin7-chloro-5- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluormphenyl) pyrido [2,3-d] pyrimidine
Zu 0,1 g (2,67 mmol) 5-(4-Methylpiperidin-1-yl)-6-(2,4,6-trifluorphenyl)pyrido[2,3-d]py- rimidin-7-ol in 1,5 ml Phosphoroxychlorid gab man 0,09 g (0,43 mmol) Phosphorpenta- chlorid und rührte das Gemisch 5 Stunden bei 120 °C. Man goss das Reaktionsgemisch danach auf Wasser, stellte mit wässriger Natriumcarbonatlösung alkalisch und extrahierte das wässrige Gemisch mit Essigester. Man trennte die organische Phase ab, trocknete sie, filtrierte das Trockenmittel ab und engte ein. Den erhaltenen Rückstand chromatographierte man an Kieselgel (Cyclohexan/Essigester), wobei man nach dem Einengen bis zur Trockne 0,05 g (48 %) der Titelverbindung erhielt. In analoger Weise wurden die in den nachfolgenden Tabellen 2 bis 9 angegebenen Verbindungen der allgemeinen Formeln La, l.b und l.c erhalten.To 0.1 g (2.67 mmol) of 5- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) pyrido [2,3-d] pyrimidin-7-ol in 1.5 ml of phosphorus oxychloride was added to 0.09 g (0.43 mmol) of phosphorus pentachloride and the mixture was stirred at 120 ° C. for 5 hours. The reaction mixture was then poured onto water, made alkaline with aqueous sodium carbonate solution and the aqueous mixture was extracted with ethyl acetate. The organic phase was separated off, dried, filtered off the drying agent and concentrated. The residue obtained was chromatographed on silica gel (cyclohexane / ethyl acetate), giving 0.05 g (48%) of the title compound after concentration to dryness. The compounds of the general formulas La, lb and lc given in Tables 2 to 9 below were obtained in an analogous manner.
Tabelle 2:Table 2:
Tabelle 3: Table 3:
Tabelle 4: Table 4:
Tabelle 5:Table 5:
Tabelle 6: Table 6:
Tabelle 7 Table 7
Tabelle 8Table 8
Tabelle 9Table 9
Anwendungsbeispiele: Application examples:
Die Wirkstoffe wurden als Stammlösung aufbereitet mit 0,25 Gew.-% Wirkstoff in Ace- ton oder DMSO (Dimethylsulfoxid). Dieser Lösung wurde 1 Gew.-% Emulgator Unipe- rol® EL (Netzmittel mit Emulgier- und Dispergierwirkung auf der Basis ethoxylierter Alkylphenole) zugesetzt und entsprechend der gewünschten Konzentration mit Wasser verdünnt.The active ingredients were prepared as a stock solution with 0.25% by weight of active ingredient in acetone or DMSO (dimethyl sulfoxide). 1% by weight of the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration.
Wirksamkeit gegen die Blattfleckenkrankheit an Weizen verursacht durch Leptosphae- ria nodorum bei protektiver AnwendungEfficacy against leaf blotch disease in wheat caused by Leptosphereia nodorum when used protectively
Töpfe mit Weizenpflanzen der Sorte "Kanzler" wurden mit einer wässriger Suspension in der unten angegebenen Wirkstoffkonzentration bis zur Tropfnässe besprüht. Am folgenden Tag wurden die Töpfe mit einer wässrigen Sporensuspension von Lep- tosphaeria nodorum inokuliert. Anschließend wurden die Pflanzen in einer Kammer bei 20 °C und maximaler Luftfeuchte aufgestellt. Nach 8 Tagen hatte sich die Blattfleckenkrankheit auf den unbehandelten, jedoch infizierten Kontrollpflanzen so stark entwickelt, dass der Befall visuell in % ermittelt werden konnte.Pots with wheat plants of the "Kanzler" variety were sprayed to runoff point with an aqueous suspension in the active compound concentration given below. At the the following day the pots were inoculated with an aqueous spore suspension of Leptosphaeria nodorum. The plants were then placed in a chamber at 20 ° C. and maximum air humidity. After 8 days, the leaf spot disease on the untreated but infected control plants had developed to such an extent that the infestation could be determined visually in%.

Claims

Patentansprücheclaims
1. Bicyclische Verbindungen der allgemeinen Formel I1. Bicyclic compounds of the general formula I
worin X, Y unabhängig voneinander für N oder C-R4 stehen; n für 1 , 2, 3, 4 oder 5 steht; Ra für Halogen, Cyano, CrCβ-Alkyl, CrC6-Alkoxy, CrC6-Halogenalkyl, Cι-C6-Halogenalkoxy, C2-C6-Alkenyl, C2-C6-Alkenyloxy oder C(O)R5 steht; R1 Halogen, Cyano, C C6-Alkyl, CrC6-Halogenalkyl, C2-C6- Alkenyl, C2- C6-Alkinyl, C3-C8-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, C5-C8-Cycloalkenyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, OR6, SR6 oder NR7R8 bedeutet; R2 Halogen, Cyano, CrC6-Alkyl, CrCe-Halogenalkyl, C2-C6-Alkenyl, C2- Ce-Alkinyl, C3-C8-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, C5-C8-Cycloalkenyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, OR6, SR6 oder NR7R8 bedeutet; R3 für Wasserstoff, Cι-C6-Alkyl, C C6-Halogenalkyl oder C3-C6- Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, steht; R4 für Wasserstoff, Halogen, CrC6-AlkyI, CrC6-Halogenalkyl oder C3- C6-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, steht; R5 Wasserstoff, OH, C C6-Alkyl, CrC6-Alkoxy, d-C6-Halogenalkyl, d-Ce-Halogenalkoxy, C2-C6-Alkenyl, d-C6-Alkylamino oder Di-C C6- alkylamino, Piperidin-1 -yl, Pyrrolidin-1 -yl oder Morpholin-4-yl bedeutet; R6 Wasserstoff, CrC8-Alkyl, C C6-Halogenalkyl, Phenyl-C C4-alkyl, worin Phenyl mit Halogen, Alkyl oder Alkoxy ein- oder mehrfach sub- stituiert sein kann, C2-C6-Alkenyl oder COR9 bedeutet; R7, R8 unabhängig voneinander für Wasserstoff, CrC10-Alkyl, C2-C-|0- Alkenyl, C4-C10-Alkadienyl, C2-C10-Alkinyl, C3-C8-Cycloalkyl, C5-C8- Cycloalkenyl, C -C 0-Bicycloalkyl, Phenyl, Phenyl-C C4-alkyl, Naphthyl, ein 5- oder 6-gliedriger, gesättigter oder teilweise ungesättigter Heterocyclus, der 1 , 2 oder 3 Heteroatome, ausgewählt unter N, O und S, als Ringglieder aufweisen kann, oder ein 5- oder 6-gliedriger, aromatischer Heterocyclus, der 1 , 2 oder 3 Heteroatome, ausgewählt unter N, O und S, als Ringglieder aufwei- sen kann, wobei die als R7, R8 genannten Reste teilweise oder vollständig halo- geniert sein können und/oder 1 , 2 oder 3 Reste Rb aufweisen können, wobei Rb ausgewählt ist unter Cyano, Nitro, OH, CrC6-Alkyl, CrC6-Alkoxy, d-Ce-Halogenalkyl, CrC6-Halogenalkoxy, CrC6-Alkylthio, C2-C6- Alkenyl, C2-C6-Alkenyloxy, C2-C6- Alkinyl, C2-C6-Alkinyloxy, d-C6- Alkylamino, Di-d-Ce-alkylamino, Piperidin-1-yl, Pyrrolidin-1 -yl oder Morpholin-4-yl; R7 mit R8 auch gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen 5-, 6 oder 7-gliedrigen, gesättigten oder ungesättigten Heterocyclus bilden können, der 1 , 2, 3 oder 4 weitere Heteroatome, ausgewählt unter O, S, N und NR10 als Ringglied aufweisen kann, der teilweise oder vollständig halogeniert sein kann und der 1 , 2 oder 3 der Reste Rb aufweisen kann; und R9, R10 unabhängig voneinander Wasserstoff oder C C6-Alkyl bedeuten; sowie die landwirtschaftlich verträglichen Salze von Verbindungen I, ausgenommen Verbindungen der allgemeinen Formel I, worin R1 für OH steht, wenn gleichzeitig Y und X jeweils für C-R4 stehen; sowie ausgenommen 2,4-Dichlor-3-(o-methoxyphenyl)-1 ,8-naphthyridin. wherein X, Y are independently N or CR 4 ; n represents 1, 2, 3, 4 or 5; R a is halogen, cyano, CrC β alkyl, -C 6 alkoxy, -C 6 haloalkyl, Cι-C 6 haloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy or C (O) R 5 stands; R 1 is halogen, cyano, CC 6 alkyl, -C 6 haloalkyl, C 2 -C 6 - alkenyl, C 2 - C 6 alkynyl, C 3 -C 8 cycloalkyl, optionally substituted with alkyl and / or halogen single or is multiply substituted, C 5 -C 8 cycloalkenyl, which is optionally mono- or polysubstituted with alkyl and / or halogen, is OR 6 , SR 6 or NR 7 R 8 ; R 2 halogen, cyano, CrC 6 alkyl, CrCe haloalkyl, C 2 -C 6 alkenyl, C 2 - Ce alkynyl, C 3 -C 8 cycloalkyl, optionally with one or more alkyl and / or halogen is C 5 -C 8 cycloalkenyl which is optionally mono- or polysubstituted with alkyl and / or halogen, OR 6 , SR 6 or NR 7 R 8 ; R 3 represents hydrogen, -CC 6 alkyl, CC 6 haloalkyl or C 3 -C 6 cycloalkyl, which is optionally mono- or polysubstituted with alkyl and / or halogen; R 4 is hydrogen, halogen, C r C 6 -AlkyI, -C 6 haloalkyl or C 3 - C 6 -cycloalkyl which is optionally monosubstituted by alkyl and / or halogen or poly-substituted; R 5 is hydrogen, OH, CC 6 -alkyl, C r C 6 -alkoxy, dC 6 -haloalkyl, d-Ce-haloalkoxy, C 2 -C 6 -alkenyl, dC 6 -alkylamino or di-C C 6 -alkylamino, Piperidin-1 -yl, pyrrolidin-1 -yl or morpholin-4-yl; R 6 is hydrogen, CrC 8 -alkyl, CC 6 -haloalkyl, phenyl-C C 4 -alkyl, where phenyl can be substituted one or more times with halogen, alkyl or alkoxy, C 2 -C 6 -alkenyl or COR 9 means; R 7 , R 8 independently of one another for hydrogen, C r C 10 alkyl, C 2 -C- | 0 - alkenyl, C 4 -C 10 alkadienyl, C 2 -C 10 alkynyl, C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, C -C 0 bicycloalkyl, phenyl, phenyl-C C 4 -alkyl, naphthyl, a 5- or 6-membered, saturated or partially unsaturated heterocycle which can have 1, 2 or 3 heteroatoms, selected from N, O and S, as ring members, or a 5- or 6-membered, aromatic Heterocycle, which can have 1, 2 or 3 heteroatoms, selected from N, O and S, as ring members, it being possible for the radicals mentioned as R 7 , R 8 to be partially or completely halogenated and / or 1, 2 or R 3 may have b, wherein R b is selected from cyano, nitro, OH, -C 6 alkyl, -C 6 alkoxy, CrC-Ce-haloalkyl, d 6 -haloalkoxy, -C 6 -alkylthio, C 2 -C 6 - alkenyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyl, C 2 -C 6 alkynyloxy, dC 6 - alkylamino, di-d-Ce-alkylamino, piperidin-1-yl, pyrrolidin-1 - yl or morpholin-4-yl; R 7 with R 8 together with the nitrogen atom to which they are attached can also form a 5-, 6 or 7-membered, saturated or unsaturated heterocycle which has 1, 2, 3 or 4 further heteroatoms selected from O, S , N and NR 10 can have as a ring member, which can be partially or completely halogenated and which can have 1, 2 or 3 of the radicals R b ; and R 9 , R 10 independently of one another are hydrogen or CC 6 alkyl; and the agriculturally acceptable salts of compounds I, with the exception of compounds of the general formula I in which R 1 is OH when Y and X are each CR 4 ; as well as except 2,4-dichloro-3- (o-methoxyphenyl) -1, 8-naphthyridine.
2. Verbindungen nach Anspruch 1 der allgemeinen Formel I, worin Y und X jeweils für C-R4 stehen.2. Compounds according to claim 1 of the general formula I, wherein Y and X each represent CR 4 .
3. Verbindungen nach Anspruch 1 der allgemeinen Formel I, worin Y für N steht und X für C-R4 steht.3. Compounds according to claim 1 of general formula I, wherein Y is N and X is CR 4 .
4. Verbindungen nach Anspruch 1 der allgemeinen Formel l, worin Y für C-R4 steht und X für N steht. 4. Compounds according to claim 1 of the general formula I, wherein Y is CR 4 and X is N.
5. Verbindungen nach einem der vorhergehenden Ansprüche der allgemeinen Formel I, worin R4 für Wasserstoff, d-C6-Alkyl oder CrC6-Halogenalkyl steht.5. Compounds according to any one of the preceding claims of the general formula I wherein R 4 is hydrogen, dC 6 alkyl or CrC is 6 haloalkyl.
6. Verbindungen nach einem der vorhergehenden Ansprüche der allgemeinen For- mel I, worin n für 2, 3, 4 oder 5 steht.6. Compounds according to one of the preceding claims of the general formula I, in which n is 2, 3, 4 or 5.
7. Verbindungen nach einem der vorhergehenden Ansprüche der allgemeinen Formel I, worin die Gruppe7. Compounds according to any one of the preceding claims of general formula I, wherein the group
steht, worin Ra1 für Fluor, Chlor, Trifluormethyl oder Methyl; Ra2 für Wasserstoff oder Fluor; Ra3 für Wasserstoff, Fluor, Chlor, Cyano, C C4-Alkyl, C C4-Alkoxy oder d-C -Alkoxycarbonyl; Ra4 für Wasserstoff, Chlor oder Fluor; Ra5 für Wasserstoff, Fluor, Chlor, C C4-Alkyl oder d-C -Alkoxy stehen. where R a1 is fluorine, chlorine, trifluoromethyl or methyl; R a2 for hydrogen or fluorine; R a3 represents hydrogen, fluorine, chlorine, cyano, CC 4 -alkyl, CC 4 -alkoxy or dC -alkoxycarbonyl; R a4 for hydrogen, chlorine or fluorine; R a5 represents hydrogen, fluorine, chlorine, CC 4 -alkyl or dC -alkoxy.
8. Verbindungen nach einem der vorhergehenden Ansprüche der allgemeinen Formel I, worin R1 für eine Gruppe NR7R8 steht, worin wenigstens einer der Reste R7, R8 von Wasserstoff verschieden ist.8. Compounds according to any one of the preceding claims of general formula I, wherein R 1 represents a group NR 7 R 8 , wherein at least one of the radicals R 7 , R 8 is different from hydrogen.
9. Verbindungen nach Anspruch 8 der allgemeinen Formel I, worin R7 für d-Ce-Alkyl, C3-C8-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, CrC6-Halogenalkyl, Phenyl-C C4-alkyl, C2-C6-A!kenyl oder C2-C6-Alkinyl steht; R8 für Wasserstoff, d-C6-Alkyl oder C2-C6-Alkenyl steht; oder R7, R8 gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, für einen gesättigten oder teilweise ungesättigten 5-, 6- oder 7-gliedrigen Stickstoff- heterocyclus stehen, der 1 weiteres Heteroatom, ausgewählt unter O, S, und NR10 als Ringglied aufweisen kann, und der 1 oder 2 Substituenten, ausgewählt unter CrC6-Alkyl, -Ce-Halogenalkyl, Halogen und Hydroxy, aufweisen kann, wobei R10 die in Anspruch 1 angegebene Bedeutung auf- weist.9. Compounds according to claim 8 of the general formula I, wherein R 7 for d-Ce-alkyl, C 3 -C 8 -cycloalkyl, which is optionally mono- or polysubstituted with alkyl and / or halogen, CrC 6 -haloalkyl, phenyl -C C 4 alkyl, C 2 -C 6 -A! Kenyl or C 2 -C 6 alkynyl; R 8 represents hydrogen, dC 6 alkyl or C 2 -C 6 alkenyl; or R 7 , R 8 together with the nitrogen atom to which they are attached represent a saturated or partially unsaturated 5-, 6- or 7-membered nitrogen heterocycle, the 1 further heteroatom selected from O, S and NR 10 as a ring member, and which may have 1 or 2 substituents selected from CrC 6 alkyl, -Ce haloalkyl, halogen and hydroxy, where R 10 has the meaning given in claim 1. has.
10. Verbindungen nach Anspruch 1 der allgemeinen Formel I, worin R1 für Hydroxy steht und einer der Reste Y oder X für N steht.10. Compounds according to claim 1 of the general formula I, wherein R 1 is hydroxy and one of the radicals Y or X is N.
1 1. Verbindungen nach einem der Ansprüche 1 bis 7 der allgemeinen Formel I, worin R1 für Halogen steht. 2. Verbindungen nach Anspruch 1 , worin R2 für Hydroxy steht, Y für C-R4 steht und X für C-R4 oder N steht.1 1. Compounds according to any one of claims 1 to 7 of the general formula I, wherein R 1 is halogen. 2. Compounds according to claim 1, wherein R 2 is hydroxy, Y is CR 4 and X is CR 4 or N.
13. Verbindungen nach einem der Ansprüche 1 bis 11 , worin R2 für Halogen, d-C6- Alkyl oder C C6-Halogenalkyl steht.13. Compounds according to any one of claims 1 to 11, wherein R 2 is halogen, dC 6 alkyl or CC 6 haloalkyl.
14. Verwendung von Verbindung der allgemeinen Formel I14. Use of compound of general formula I.
woπn X, Y unabhängig voneinander für N oder C-R4 stehen; n für 1 , 2, 3, 4 oder 5 steht; Ra für Halogen, Cyano, d-Ce-Alky!, d-C6-Alkoxy, C C6-Halogenalkyl, d-Ce-Halogenalkoxy, C2-C8-Alkenyl, C2-C8-Alkenyloxy oder C(O)R5 steht; R1 Halogen, Cyano, C C6-Alkyl, C C6-Halogenalkyl, C2-C6-Alkenyl, C2- Ce-Alkinyl, C3-C8-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, C5-C8-Cycloalkenyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, OR6, SR6 oder NR7R8 bedeutet; R2 Halogen, Cyano, d-C6-Alkyl, d-Ce-Halogenalkyl, C2-C6-Alkenyl, C2- Ce-Alkinyl, C3-C8-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, C5-C8-Cycloalkenyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, OR6, SR6 oder NR7R8 bedeutet; R3 für Wasserstoff, CrCe-Alkyl, C C6-Halogenalkyl oder C3-C6- Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, steht; R4 für Wasserstoff, Halogen, CrC6-Alkyl, C C6-Halogenalkyl oder C3- Ce-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, steht; R5 Wasserstoff, OH, CrC6-Alkyl, CrC6-Alkoxy, CrCe-Halogenalkyl; C Ce-Halogenalkoxy, C2-C6-Alkenyl, CrC6-Alkylamino oder Di- C C6- alkylamino, Piperidin-1-yl, Pyrrolidin-1-yl oder Morpholin-4-yl bedeu- tet; where X, Y are independently N or CR 4 ; n represents 1, 2, 3, 4 or 5; R a is halogen, cyano, d-Ce-alky !, dC 6 alkoxy, CC 6 haloalkyl, d-Ce-haloalkoxy, C 2 -C 8 alkenyl, C 2 -C 8 alkenyloxy or C (O) R 5 is; R 1 is halogen, cyano, CC 6 -alkyl, CC 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 - Ce-alkynyl, C 3 -C 8 -cycloalkyl, which is optionally substituted with alkyl and / or halogen is multiply substituted, C 5 -C 8 cycloalkenyl, which is optionally mono- or polysubstituted with alkyl and / or halogen, is OR 6 , SR 6 or NR 7 R 8 ; R 2 is halogen, cyano, dC 6 -alkyl, d-Ce-haloalkyl, C 2 -C 6 -alkenyl, C 2 - Ce-alkynyl, C 3 -C 8 -cycloalkyl, which may be mixed with alkyl and / or halogen or is multiply substituted, C 5 -C 8 cycloalkenyl, which is optionally mono- or polysubstituted with alkyl and / or halogen, is OR 6 , SR 6 or NR 7 R 8 ; R 3 represents hydrogen, CrCe-alkyl, CC 6 -haloalkyl or C 3 -C 6 -cycloalkyl, which is optionally mono- or polysubstituted by alkyl and / or halogen; R 4 represents hydrogen, halogen, CrC 6 alkyl, CC 6 haloalkyl or C 3 - Ce cycloalkyl, which is optionally mono- or polysubstituted by alkyl and / or halogen; R 5 is hydrogen, OH, CrC 6 alkyl, C r C 6 alkoxy, CrCe haloalkyl; C Ce-haloalkoxy, C 2 -C 6 alkenyl, C r C 6 alkylamino or di-CC 6 alkylamino, piperidin-1-yl, pyrrolidin-1-yl or morpholin-4-yl means;
R6 Wasserstoff, C C6-Alkyl, d-C6-Halogenalkyl, Phenyl-d-C4-alkyl, worin Phenyl mit Halogen, Alkyl oder Alkoxy ein- oder mehrfach substituiert sein kann, C2-C6-Alkenyl oder COR9 bedeutet; R7, R8 unabhängig voneinander für Wasserstoff, d-Cι0-Alkyl, C2-C10- Alkenyl, C -d0-Alkadienyl, C2-Cιo-Alkinyl, Ca-Ca-Cycloalkyl, C5-C8- Cycloalkenyl, C5-C10-Bicycloalkyl, Phenyl, Phenyl-d-C -alkyl, Naphthyl, ein 5- oder 6-gliedriger, gesättigter oder teilweise ungesättigter Heterocyclus, der 1 , 2 oder 3 Heteroatome, ausgewählt unter N, O und S, als Ringglieder aufweisen kann, oder ein 5- oder 6-gliedriger, aromatischer Heterocyclus, der 1 , 2 oder 3 Heteroatome, ausgewählt unter N, O und S, als Ringglieder aufweisen kann, wobei die als R7, R8 genannten Reste teilweise oder vollständig halo- geniert sein können und/oder 1 , 2 oder 3 Reste Rb aufweisen können, wobei Rb ausgewählt ist unter Cyano, Nitro, OH, d-C6-Alkyl, d-C6-Alkoxy, CrCe-Halogenalkyl, d-C6-Halogenalkoxy, d-C6-Alkylthio, C2-C6- Alkenyl, C2-C6-Alkenyloxy, C2-C6-Alkinyl, C2-C6-Alkinyloxy, d-C6- Atkyiamino, Di-CrC6-alkylamino, Piperidin-1 -yl, Pyrrolidin-1 -yl oder Morpholin-4-yl; R7 mit R8 auch gemeinsam mit dem Stickstoff atom, an das sie gebunden sind, einen 5-, 6 oder 7-gliedrigen, gesättigten oder ungesättigten Heterocyclus bilden können, der 1 , 2, 3 oder 4 weitere Heteroatome, aus- gewählt unter O, S, N und NR10 als Ringglied aufweisen kann, der teilweise oder vollständig halogeniert sein kann und der 1 , 2 oder 3 der Reste R aufweisen kann; und R9, R10 unabhängig voneinander Wasserstoff oder CrC6-Alkyl bedeuten; und von deren landwirtschaftlich verträglichen Salzen zur Bekämpfung von pflanzenpathogenen Pilzen.R 6 is hydrogen, CC 6 -alkyl, dC 6 -haloalkyl, phenyl-dC 4 -alkyl, where phenyl can be mono- or polysubstituted by halogen, alkyl or alkoxy, is C 2 -C 6 -alkenyl or COR 9 ; R 7, R 8 are each independently hydrogen, d-Cι 0 alkyl, C 2 -C 10 - alkenyl, C -d 0 -alkadienyl, C 2 -Cιo-alkynyl, Ca-Ca-cycloalkyl, C 5 -C 8 - Cycloalkenyl, C 5 -C 10 bicycloalkyl, phenyl, phenyl-dC-alkyl, naphthyl, a 5- or 6-membered, saturated or partially unsaturated heterocycle, the 1, 2 or 3 heteroatoms selected from N, O and S. , as ring members, or a 5- or 6-membered aromatic heterocycle, which may have 1, 2 or 3 heteroatoms selected from N, O and S, as ring members, the radicals mentioned as R 7 , R 8 partially or can be completely halogenated and / or can have 1, 2 or 3 radicals R b , where R b is selected from cyano, nitro, OH, dC 6 alkyl, dC 6 alkoxy, CrCe haloalkyl, dC 6 - Haloalkoxy, dC 6 alkylthio, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyl, C 2 -C 6 alkynyloxy, dC 6 - atkyiamino, di-CrC 6 alkylamino , Piperidin-1 -yl, pyrrolidin-1 -yl or Morpholin-4-yl; R 7 together with R 8 together with the nitrogen atom to which they are attached can form a 5-, 6 or 7-membered, saturated or unsaturated heterocycle which contains 1, 2, 3 or 4 further heteroatoms, selected from O, S, N and NR 10 can have as a ring member, which can be partially or completely halogenated and which can have 1, 2 or 3 of the radicals R; and R 9 , R 10 are independently hydrogen or C r C 6 alkyl; and of their agriculturally acceptable salts for controlling phytopathogenic fungi.
15. Verfahren zur Bekämpfung von pflanzenpathogenen Pilzen, dadurch gekenn- zeichnet, dass man die Pilze, oder die vor Pilzbefall zu schützenden Materialien, Pflanzen, den Boden oder Saatgüter mit einer wirksamen Menge einer Verbindung der allgemeinen Formel I gemäß Anspruch 14 und/oder mit einem landwirtschaftlich verträglichen Salz von I behandelt.15. A method for combating phytopathogenic fungi, characterized in that the fungi, or the materials, plants, soil or seeds to be protected against fungal attack, with an effective amount of a compound of the general formula I according to claim 14 and / or with an agriculturally acceptable salt of I treated.
16. Mittel zur Bekämpfung von pflanzenpathogenen Pilzen, enthaltend wenigstens eine Verbindung der allgemeinen Formel I gemäß Anspruch 14 und/oder ein landwirtschaftlich verträgliches Salz von I und wenigstens einen flüssigen oder festen Trägerstoff.16. Agent for combating phytopathogenic fungi, comprising at least one compound of the general formula I according to claim 14 and / or an agriculturally acceptable salt of I and at least one liquid or solid carrier.
17. Ketone der allgemeinen Formel IIID,17. ketones of the general formula IIID,
worin W d-C6-Alkyl, d-Ce-Halogenalkyl, C2-C6- Alkenyl, C2-C6-Alkinyl, C3-C8-Cycloalkyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, C5-C8-Cycloalkenyl, das gegebenenfalls mit Alkyl und/oder Halogen ein- oder mehrfach substituiert ist, bedeutet, Ra1 Fluor, Chlor, Trifluormethyl oder Methyl bedeutet; Ra2 Wasserstoff oder Fluor bedeutet;wherein W dC 6 alkyl, d-Ce haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, optionally substituted one or more times with alkyl and / or halogen is C 5 -C 8 cycloalkenyl, which is optionally mono- or polysubstituted by alkyl and / or halogen, R a1 is fluorine, chlorine, trifluoromethyl or methyl; R a2 represents hydrogen or fluorine;
Ra3 Wasserstoff, Fluor, Chlor, Cyano, C C -Alkyl, C C4-Alkoxy, oder C C4- Alkoxycarbonyl bedeutet; Ra4 Wasserstoff, Chlor oder Fluor bedeutet;R a3 is hydrogen, fluorine, chlorine, cyano, CC alkyl, CC 4 alkoxy, or CC 4 alkoxycarbonyl; R a4 represents hydrogen, chlorine or fluorine;
Ra5 Wasserstoff, Fluor, Chlor, d-C -Alkyl oder C C4-Alkoxy bedeutet. R a5 means hydrogen, fluorine, chlorine, dC -alkyl or CC 4 -alkoxy.
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US20060160811A1 (en) 2006-07-20
AR046075A1 (en) 2005-11-23
AU2004259269A1 (en) 2005-02-03
WO2005010000A2 (en) 2005-02-03
BRPI0412704A (en) 2006-09-26
WO2005010000A3 (en) 2005-05-19
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CA2532917A1 (en) 2005-02-03

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