WO2014095534A1 - Nouveaux triazoles et imidazoles substitués et leur utilisation en tant que fongicides - Google Patents

Nouveaux triazoles et imidazoles substitués et leur utilisation en tant que fongicides Download PDF

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WO2014095534A1
WO2014095534A1 PCT/EP2013/076276 EP2013076276W WO2014095534A1 WO 2014095534 A1 WO2014095534 A1 WO 2014095534A1 EP 2013076276 W EP2013076276 W EP 2013076276W WO 2014095534 A1 WO2014095534 A1 WO 2014095534A1
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compounds
alkyl
iii
special embodiment
cycloalkyl
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PCT/EP2013/076276
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Wassilios Grammenos
Ian Robert CRAIG
Nadege Boudet
Bernd Müller
Jochen Dietz
Erica May Wilson LAUTERWASSER
Jan Klaas Lohmann
Thomas Grote
Egon Haden
Ana Escribano Cuesta
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Basf Se
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    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/08—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing alicyclic rings

Definitions

  • the present invention relates to new substituted triazoles and imidazoles of the formula I
  • the present invention relates to a process for preparing compounds of the formula I .
  • the present invention relates to agrochemical compositions, comprising an auxilia- ry and at least one compound of formula I an N-oxide or an agriculturally acceptable salt thereof.
  • the present invention relates to the use of a compound of the formula I and/or of an agriculturally acceptable salt thereof or of the compositions for combating phytopathogenic fungi. Furthermore the present invention relates to a method for combating harmful fungi, comprising treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of at least one compound of formula I or with a composition.
  • the present invention relates to seed, coated with at least one compound of the formula I and/or an agriculturally acceptable salt thereof or with a composition in an amount of from 0.1 to 10 kg per 100 kg of seed.
  • the compounds according to the present invention differ from those described in the above- mentioned publications inter alia by the substitution of the phenyl ring and the epoxide group. In many cases, in particular at low application rates, the fungicidal activity of the known fungi- cidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic harmful fungi.
  • R is O or CH 2 ;
  • Q is O or CH 2 ;
  • T is O or CH 2 ;
  • R or Q or T is O
  • A is CH or N ;
  • R D is hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl , C2-C6-haloalkenyl, C2-C6- alkynyl, C 2 -C6-haloalkynyl or CN ;
  • R 3 is unsubstituted or further substituted by one, two, three or four R 3a ;
  • R 3a is independently selected from halogen, CN, NO2, OH, Ci-C 4 -alkyl, Ci-C4-haloalkyl,
  • n 0, 1 , 2, 3 or 4;
  • Y is a direct bond or a divalent group selected from the group consisting of -0-, -S-, SO-,
  • R 8 , R 9 ,R 10 , R 11 , R 12 , R 13 , R 14 , R 15 are independently selected from hydrogen, halogen, CN, nitro, OH , Ci-C4-alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C4-halogenalkoxy;
  • n 0, 1 , 2, 3, 4 or 5;
  • R 4 is independently selected from halogen, CN, NO2, OH, SH , Ci-C6-alkyl, C1-C6- alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C8-cycloalkyloxy, N H 2 ,
  • R 4a is independently selected from halogen, CN , NO2, OH, Ci-C 4 -alkyl, Ci-C 4 - haloalkyl, C 3 -Ce-cycloalkyl, C 3 -Ce-halocycloalkyl, Ci-C 4 -alkoxy and C1-C4- haloalkoxy; p is 0, 1 or 2;
  • x 0, 1 , 2, 3 or 4;
  • R 5 is H, halogen, CN, N0 2 , OH, SH, Ci-C 6 -alkyl, d-C 6 -alkoxy, Ci-C 6 -alkylthio, Ci-C 6 -alkylsul- finyl, Ci-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkynyl, C 3 -C8-cycloalkyl, C 3 -Ce- cycloalkyloxy, C 3 -C 8 -cycloalkyl-Ci-C 4 -alkyl, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 ,
  • R 5a is independently selected from halogen, CN, N0 2 , OH, SH, NH 2 , Ci-C 6 -alkyl, Ci-C 6 - haloalkyl, C3-Cs-cycloalkyl, C 3 -C8-halocycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio and Ci-C4-alkoxy-Ci-C 4 -alkyl;
  • R 6 is H or is selected from the substituents defined for R 5 , wherein the aliphatic, alicyclic and aromatic moieties of R 6 are unsubstituted or substituted by one, two, three or four or up to the maximum possible number of R 6a , wherein R 6a is defined as R 5a ;
  • R 5 and R 6 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six- or seven-membered carbocycle or a saturated or partially unsaturated three-, four-, five-, six- or seven-membered heterocycle, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbo- or heterocycle is unsubstituted or carries one, two, three or four substituents independently selected from halogen, CN, N0 2 , OH, SH, NH 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl and phenoxy; and wherein one
  • R 55 , R 56 are independently selected from hydrogen, halogen, CN, N0 2 , OH, SH, NH 2 ,
  • Ci-C6-alkyl Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio,
  • R 7 is independently selected from Ci-C6-alkyl, C 2 -C6-alkenyl, C2-C6-alkynyl, C 3 -C8-cycloalkyl, wherein each of R 7 is unsubstituted or further substituted by one, two, three or four R 7a ; wherein
  • R 7a is independently selected from halogen, OH and Ci-C6-alkoxy
  • R 7 R 71 and R 72 together with the carbon atom(s) to which they are bound form a saturated three-, four-, five-, six- or seven-membered carbocycle or heterocycle, wherein the heterocycle contains one, two, three or four O atoms,
  • o 0, 1 , 2, 3 or 4;
  • the present invention provides a process for preparing compounds of the formula I. Furthermore the present invention provides an agrochemical composition, comprising an auxiliary and at least one compound of formula I an N-oxide or an agriculturally acceptable salt thereof.
  • the present invention provides a method for combating harmful fungi, comprising treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of at least one compound of formula I or with a composition.
  • the present invention provides seed, coated with at least one compound of the formula I and/or an agriculturally acceptable salt thereof or with a composition in an amount of from 0.1 to 10 kg per 100 kg of seed.
  • the prefix C x -C y denotes the number of possible carbon atoms in the particular case.
  • halogen fluorine, bromine, chlorine or iodine, especially fluorine, chlorine or bromine;
  • alkyl and the alkyl moieties of composite groups such as, for example, alkoxy, alkylamino, alkoxycarbonyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 10 carbon atoms, for example Ci-Cio-akyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1- methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3- methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, hexyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1
  • Ci-C4-alkyl refers to a straight-chained or branched alkyl group having 1 to 4 carbon atoms, such as methyl, ethyl, propyl (n-propyl), 1 -methylethyl (iso-propoyl), butyl, 1 -methylpropyl (sec-butyl), 2-methylpropyl (iso-butyl), 1 ,1-dimethylethyl (tert.
  • haloalkyl straight-chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above.
  • the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluorine, chlorine or bromine.
  • the alkyl groups are partially or fully halogenated by different halogen atoms; in the case of mixed halogen substitutions, the combination of chlorine and fluorine is preferred.
  • (Ci-C3)-haloalkyl more preferably (Ci-C 2 )-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloro- fluoromethyl, 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 or 1 ,1 ,1 -trifluoroprop-
  • alkenyl and also the alkenyl moieties in composite groups such as alkenyloxy: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and one double bond in any position.
  • alkenyloxy unsaturated straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and one double bond in any position.
  • small alkenyl groups such as (C2-C4)-alkenyl
  • larger alkenyl groups such as (C 5 -C8)-alkenyl.
  • alkenyl groups are, for example, C 2 -C6-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, 2-methyl-3-butenyl, 2-methyl-3-butenyl,
  • alkynyl and the alkynyl moieties in composite groups straight-chain or branched hydrocarbon groups having 2 to 10 carbon atoms and one or two triple bonds in any position, for example C2- C6-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-hexyn
  • bicyclic radicals comprise bicyclo[2.2.1]heptyl, bicyclo[3.1 .1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
  • optionally substituted Ca-Ce-cycloalkyl means a cycloalkyl radical having from 3 to 8 carbon atoms, in which at least one hydrogen atom, for example 1 , 2, 3, 4 or 5 hydrogen atoms, is/are replaced by substituents which are inert under the conditions of the reaction.
  • inert substituents are CN, Ci-C6-alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, and Ci-C4-alkoxy-Ci-C6-alkyl;
  • halocycloalkyl and the halocycloalkyl moieties in halocycloalkoxy, halocycloalkylcarbonyl and the like monocyclic saturated hydrocarbon groups having 3 to 10 carbon ring members (as mentioned above) in which some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;
  • alkoxy an alkyl group as defined above which is attached via an oxygen, preferably having 1 to 10, more preferably 2 to 6, carbon atoms.
  • Examples are: methoxy, ethoxy, n-propoxy, 1 -methyl- ethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1 ,1 -dimethylethoxy, and also for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethyl- propoxy, 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-d i methyl butoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-
  • Ci-C4-alkoxy groups, such as methoxy, ethoxy, n-propoxy, 1 -methylethoxy, butoxy, 1- methyhpropoxy, 2-methylpropoxy or 1 ,1 -dimethylethoxy.
  • Ci-C4-alkoxy refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms which is bonded via an oxygen, at any position in the alkyl group, examples are methoxy, ethoxy, n-propoxy, 1 - methylethoxy, butoxy, 1 -methyhpropoxy, 2-methylpropoxy or 1 ,1 -dimethylethoxy.
  • halogenalkoxy alkoxy as defined above, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as described above under haloalkyl, in particular by fluorine, chlorine or bromine.
  • Examples are OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHC , OCCI3, chloro- fluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2- bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2- chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2- fluoropropoxy, 3-fluoropropoxy, 2,2-diflu
  • the compounds according to the invention may have one or more centers of chirality, and are generally obtained in the form of racemates or as diastere- omer compositions of erythro and threo forms.
  • the erythro and threo diastereomers of the compounds according to the invention can be separated and isolated in pure form, for example, on the basis of their different solubilities or by column chromatography. Using known methods, such uniform pairs of diastereomers can be used to obtain uniform enantiomers.
  • Suitable for use as antimicrobial agents are both the uniform diastereomers or enantiomers and compositions thereof obtained in the synthesis. This applies correspondingly to the fungicidal compositions.
  • the invention provides both the pure enantiomers or diastereomers and compositions thereof.
  • the scope of the present invention includes in particular the (R) and (S) isomers and the racemates of the compounds according to the invention, in particular of the formula I, which have centers of chirality.
  • Suitable compounds of the formula I according to the invention also comprise all possible stereoisomers (cis/trans isomers) and compositions thereof.
  • the compounds according to the invention may be present in various crystal modifications which may differ in their biological activity. They are likewise provided by the present invention.
  • the compounds according to the invention are capable of forming salts or adducts with inorganic or organic acids or with metal ions.
  • Suitable agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds of the formula I.
  • suitable cations are in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium and sulfoxonium ions
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hex- afluorosilicate, hexafluorophosphate, benzoate, and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • inventive compounds can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention.
  • the compounds of formula I and their N-oxides may have one or more centers of chirality, in which case they are present as pure enantiomers or pure diastereomers or as enantiomer or diastereomer compositions. Both, the pure enantiomers or diastereomers and their compositions are subject matter of the present invention.
  • the compounds of the formula I according to the invention can be prepared by different routes analogously to processes known per se of the prior art (see, for example, the prior art cited at the outset).
  • Analogs of compounds V can be prepared starting from accessible compounds II in cross- coupling / epoxidation / cyclization sequence (Journal of the American Chemical Society, 132(44), 15474-15476; 2010; Journal of the American Chemical Society, 132(23), 7878-7880; 2010; Journal of Organic Chemistry, 69(24), 8387-8393; 2004). Activation by sulfonation or hal- ogenation leads to azole compounds I.
  • the intermediate XX1 can be prepared by well described following sequence: addition of pent- 4-en-1-yl-magnesium bromide on the corresponding aldehyde X1 / oxidation (e.g. using PCC) / epoxidation (e.g. using trimethylsulfoxonium iodide).
  • the intermediate XX 1 can then react with an azole using a strong base such as KOH, and then being cyclized in situ using e.g. ozonolysis of the double bond. Subsequent dehydroxylation using e.g triethylsilane and TFA will provide the azole compound I. g
  • Aldehydes VI are known in literature or can be prepared in analogy to prior art. Reduction followed by activation (sulfonation, halogenation) enables benzyl cyanides VII, which can be transformed into THF-derivative VIII in analogy to WO2008076427A2. Reduction of the cyanide either with Hydride equivalents (eg. R5 not H DIBAH, Red-AI, H2, NaBH4) or with metal organic reagents (R5 not H; using R-M such as MeLi, MeMgX, R-Mgx, R-Li) gives hydroxyl compounds IX .
  • Hydride equivalents eg. R5 not H DIBAH, Red-AI, H2, NaBH4
  • metal organic reagents R5 not H; using R-M such as MeLi, MeMgX, R-Mgx, R-Li
  • Aldehydes VI are known in literature or can be prepared in analogy to prior art. Reduction fol- lowed by activation (sulfonation, halogenation) enables benzyl cyanides VII, which can be transformed into THF-derivative X in analogy to WO2008076427A2. Reduction of the cyanide either with hydride equivalents (eg. R 5 not H DIBAH, Red-AI, H2, NaBH4) or with metal organic reagents (R5 not H; using R-M such as MeLi, MeMgX, R-Mgx, R-Li) gives hydroxyl compounds XI. Activation of the hydroxyl group (sulfonation, halogenation) followed by substitution of with an azole compound (triazole, imidazole) leads to compounds I.
  • hydride equivalents eg. R 5 not H DIBAH, Red-AI, H2, NaBH4
  • metal organic reagents R5 not H; using R-M
  • One aspect of the invention is the following process for preparing compounds I and the respective intermediates:
  • PG is preferably THP, MOM, TMS, TES, TBDMS, TIPS, TBDPS;
  • PG is preferably THP, MOM, TMS, TES, TBDMS, TIPS, TBDPS;
  • an aspect is a process for preparing compounds of formula I as defined herein, which comprises reacting a compound of formula comprises reacting a compound of formula which comprises following steps:
  • the invention relates to a process for preparing compounds of formula I as defined herein, which comprises reacting a compound of formula comprises reacting a compound of formula which comprises following steps:
  • a further aspect of the invention are intermediate compounds of formulae II I, IV, V, VII I, IX, X, XI, wherein Z, Y, R 3 , R 5 , R 6 , R 7 , o, n, x, if applicable, are as defined herein for compounds I, as far as novel.
  • inventive compounds cannot be directly obtained by the routes described above, they can be prepared by derivatization of other inventive compounds.
  • the N-oxides may be prepared from the inventive compounds according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as metachloroper- benzoic acid (cf. WO 03/64572 or J. Med. Chem. 38(1 1 ), 1892-903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981) or oxone (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001 ).
  • the oxidation may lead to pure mono-N-oxides or to a composition of different N-oxides, which can be separated by conventional methods such as chromatography.
  • compositions of isomers If the synthesis yields compositions of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be intercon verted during work-up for use or during application (e. g. under the action of light, acids or bases). Such conversions may also take place after use, e. g. in the treatment of plants in the treated plant, or in the harmful fungus to be controlled.
  • a further embodiment of the present invention is compounds of formulae III (see above), where- in the variables Z, Y, R 3 , n are as defined and preferably defined for formula I herein and PG is preferably THP, MOM, TMS, TES, TBDMS, TIPS, TBDPS.
  • variables Z, Y, R 3 , n are as defined in tables 1 a-l to 1 a-18, 1 a-ll to 18a-ll, 1 a-lll to 9a-lll, 1 a-a to 18a-a, 1 a-b to 18a-b, 1a-c to 18a-c, 1a-IV to 10a- IV, 1 a-V to 10a-V for compounds I, wherein the substituents are specific embodiments inde- pendently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formulae IV (see above), wherein the variables Z, Y, R 3 , n are as defined and preferably defined for formula I herein and PG is preferably THP, MOM, TMS, TES, TBDMS, TIPS, TBDPS.
  • variables Z, Y, R 3 , n are as defined in tables 1a-l to 1 a-18, 1 a-ll to 18a-ll, 1 a-lll to 9a-lll, 1 a-a to 18a-a, 1 a-b to 18a-b, 1a-c to 18a-c, 1a-IV to 10a- IV, 1 a-V to 10a-V for compounds I, wherein the substituents are specific embodiments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formulae V (see above), wherein the variables Z, Y, R 3 , R 5 , R 6 , R 7 , o, n, x are as defined and preferably defined for formula I herein.
  • variables , Z, Y, R 3 , R 5 , R 6 , R 7 , o, n, x are as defined in tables 1 a-l to 1 a-18, 1a-ll to 18a-ll, 1 a-lll to 9a-lll, 1 a-a to 18a-a, 1a-b to 18a-b, 1 a-c to 18a-c, 1 a-IV to 10a-IV, 1a-V to 10a-V for compounds I, wherein the substituents are specific embodiments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formula VI (see above), wherein variables Z, Y, R 3 , n are as defined and preferably defined for formula I herein.
  • the variables Z, Y, R 3 n are as defined in tables 1a-l to 1 a-18, 1 a-ll to 18a-ll, 1 a-lll to 9a-lll, 1 a-a to 18a-a, 1a-b to 18a-b, 1a-c to 18a-c, 1 a-IV to 10a-IV, 1 a-V to 10a-V for compounds I, wherein the substituents are specific embodiments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formula VII (see above), wherein variables Z, Y, R 3 , n are as defined and preferably defined for formula I herein.
  • the variables Z, Y, R 3 n are as defined in tables 1 a-l to 1 a-18, 1 a-ll to 18a-ll, 1 a-lll to 9a-lll, 1 a-a to 18a-a, 1 a-b to 18a-b, 1 a-c to 18a-c, 1 a-l V to 10a-IV, 1 a-V to 10a-V for compounds I , wherein the substituents are specific embodiments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formula VIII (see above), wherein variables Z, Y, R 3 , R 7 , n, o are as defined and preferably defined for formula I herein.
  • the variables Z, Y, R 3 , R 7 , n, o are as defined in tables 1 a-l to 1 a-18, 1 a-l I to 18a-ll, 1 a-lll to 9a-lll, 1 a-a to 18a-a, 1 a-b to 18a-b, 1 a-c to 18a-c, 1 a-IV to 10a-IV, 1 a-V to 10a-V for compounds I, wherein the substituents are specific embodiments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formula IX, wherein the varia- bles Z, Y, R 3 , R 5 , R 6 , R 7 , o, n, x are as defined and preferably defined for formula I herein.
  • the variables Z, Y, R 3 , R 5 , R 6 , R 7 , o, n, x are as defined in tables in tables 1 a-l to 1a-18, 1a-ll to 18a-ll, 1a-lll to Gai n , 1 a-a to 18a-a, 1 a-b to 18a-b, 1 a-c to 18a-c, 1 a-IV to 10a-IV, 1a-V to 10a-V for compounds I, wherein the substituents are specific embodiments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formula X, wherein the variables Z, Y, R 3 , R 5 , R 6 , R 7 , o, n, x are as defined and preferably defined for formula I herein.
  • the variables Z, Y, R 3 , R 5 , R 6 , R 7 , o, n, x are as defined in tables in tables 1 a-l to 1a-18, 1 a-l I to 18a-ll, 1a-lll to 9a-lll, 1a-a to 18a-a, 1 a-b to 18a-b, 1 a-c to 18a-c, 1 a-IV to 10a-IV, 1 a-V to 10a-V for compounds I, wherein the substituents are specific embodiments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formula XI, wherein the variables Z, Y, R 3 , R 5 , R 6 , R 7 , o, n, x are as defined and preferably defined for formula I herein.
  • the variables Z, Y, R 3 , R 5 , R 6 ,R 7 , o, n, x are as defined in tables in tables 1 a-l to 1a-18, 1 a-l I to 18a-ll, 1 a-l 11 to 9a- III, 1 a-a to 18a-a, 1 a-b to 18a-b, 1 a-c to 18a-c, 1 a-IV to 10a-IV, 1a-V to 10a-V for compounds I, wherein the substituents are specific embodiments independently of each other or in any combination.
  • a in the compounds according to the invention is, according to one embodiment, CH.
  • a in the compounds according to the invention is, according to one further embodiment, N.
  • Q is O
  • R is Chb
  • T is CH2.
  • Q is CH2
  • R is O
  • T is CH2.
  • Q is CH2, R is CH2, T is O.
  • D in the compounds according to the invention is as defined in claim 1 .
  • D is selected from H, halogen, SH or S-C1- Ce-alkyl.
  • D is H. According to one further embodiment D is SH. According to one further embodiment D is S-CN.
  • D is halogen. In a special embodiment D is I. In a further special embodiment D is Br. In a further special embodiment D is CI.
  • D is S-Ci-Cs-alkyl preferably S-methyl, S-ethyl, S-n-propyl, S-i-propyl, S-n-butyl, S-i-butyl or S-t-butyl.
  • D is S-methyl.
  • D is S-ethyl.
  • D is S-n-propyl.
  • D is S-t-butyl.
  • D is S-Ci-C6-haloalkyl wherein Ci-C6-haloalkyl is preferably fully or partially halogenated methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl.
  • D is S-CF3.
  • D is S-CHF2.
  • D is S-CFH2.
  • D is S-CCI3.
  • D is S-CHCI2.
  • D is S-CCIH2.
  • C(CH3) CH 2 .
  • D is S-C 2 -C6-alkynyl, wherein C 2 -C6-alkynyl is preferably CCH, CH 2 CCH, CH 2 CCCH 3 .
  • D is S-CCH.
  • D is S-CCCH 3 .
  • D is S-CCCH(CH3) 2 .
  • D is S-CCC(CH 3 ) 3 .
  • D is C 2 -C6- haloalkynyl, more preferably fully or partially halogenated C 2 -C4-alkynyl.
  • D is fully or partially halogenated C 2 -alkynyl.
  • R 3 in the compounds according to the invention is, according to one embodiment, as defined in claim 1.
  • n is 0. According to one further embodiment n is 1. According to one further embodiment n is 2. According to one further embodiment n is 3. According to one further embodiment n is 4.
  • R 3 in the compounds according to the invention is, according to a further embodiment, halogen, CN, N0 2 , CrCe-alkyl, Ci-C 6 -haloalkyl, d-C 6 -alkoxy, S(0) p (Ci-C 4 -alkyl), wherein R 3 is unsubsti- tuted or further substituted by one, two, three or four R 3a ; wherein R 3a is independently selected from halogen, CN, N0 2 , OH, Ci-C 4 -alkyl, Ci-C4-haloalkyl, C 3 -C8-cycloalkyl, C 3 -C8-halocycloalkyl, Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy; p is an integrer and is 0, 1 , 2.
  • R 3 is halogen. According to a specific embodiment R 3 is CI. Ac- cording to a further specific embodiment R 3 is F. According to a further specific embodiment R 3 is Br. According to one further embodiment R 3 is CN. According to one further embodiment R 3 is N0 2 . According to one further embodiment R 3 is OH. According to one further embodiment R 3 is SH.
  • R 3 is Ci-C6-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl.
  • R 3 is methyl.
  • R 3 is ethyl.
  • R 3 is n-propyl.
  • R 3 is i- propyl.
  • R 3 is 1 -methylpropyl.
  • R 3 is n-butyl.
  • R 3 is i-butyl.
  • R 3 is t- butyl.
  • R 3 is Ci-C6-alkyl substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 3 is Ci-C6-haloalkyl, more preferably fully or partially halogenated methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl.
  • R 3 is CF 3 .
  • R 3 is CHF 2 .
  • R 3 is CFH 2 .
  • R 3 is CCI3.
  • R 3 is CHCI2.
  • R 3 is CCIH 2 .
  • R 3 is Ci-C6-alkyl, preferably Ci-C 4 -alkyl substituted by OH, more preferably CH 2 OH, CH 2 CH 2 OH, CH 2 CH 2 CH 2 OH, CH(CH 3 )CH 2 OH, CH 2 CH(CH 3 )OH, CH 2 CH 2 CH 2 CH 2 OH.
  • R 3 is CH 2 OH.
  • R 3 is Ci-C6-alkyl, preferably Ci-C 4 -alkyl substituted by CN, more preferably CH 2 CN, CH 2 CH 2 CN, CH 2 CH 2 CH 2 CN, CH(CH 3 )CH 2 CN, CH 2 CH(CH 3 )CN, CH 2 CH 2 CH 2 CH 2 CN.
  • R 3 is CH 2 CH 2 CN.
  • R 3 is CH(CH 3 )CN.
  • R 3 is Ci-C 4 -alkoxy-Ci-C6-alkyl, more preferably Ci-C 4 -alkoxy-Ci-C 4 -alkyl.
  • R 3 is CH 2 OCH 3 . In a further special embodiment R 3 is CH2CH2OCH3. In a further special embodiment R 3 is CH(CH3)OCH3. In a further special embodiment R 3 is CH(CH3)OCH2CH3. In a further special embodiment R 3 is CH2CH2OCH2CH3. According to a further specific embodiment R 3 is Ci-C4-haloalkoxy-Ci-C6-alkyl, more preferably Ci-C4-alkoxy-Ci-C4-alkyl. In a special embodiment R 3 is CH 2 OCF3. In a further special embodiment R 3 is CH2CH2OCF3. In a further special embodiment R 3 is CH2OCCI3. In a further special embodiment R 3 is CH2CH2OCCI3.
  • R 3 is Ci-C6-alkoxy, preferably Ci-C4-alkoxy.
  • R 3 is OCH3.
  • R 3 is OCH2CH3.
  • R 3 is OCH(CH3)2.
  • R 3 is OCH2CH2CH3.
  • R 3 is OC(CH 3 ) 3 .
  • R 3 is
  • C(CH 3 ) C(CH 3 )H.
  • R 3 is C 2 -C6-alkenyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 3 is C2-C6-alkynyl, preferably CCH, CH2CCH, CH2CCCH3.
  • R 3 is CCH.
  • R 3 is CCCH3.
  • R 3 is CH2CCH.
  • R 3 is CH2CCCH3.
  • R 3 is CH2CCH2CH3.
  • R 3 is C2-C6-alkynyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 3 is CC-CH3.
  • R 3 is C2-C6-haloalkynyl, more preferably fully or partially halogenated C2-C6-alkynyl.
  • I n a special embodiment R 3 is CC-CI.
  • R 3 is CC- Br.
  • R 3 is CC-l.ln a special embodiment R 3 is fully or partially halogenated C2-alkynyl.
  • R 3 is fully or partially halogenated C3-alkynyl.
  • R 3 is C2-C6-alkynyl, preferably C2-C4-alkynyl, substituted by OH, more preferably, CCOHIn a special embodiment R 3 is In a further special embodiment R 3 .
  • R 3 is Ci-C4-alkoxy-C2-C6-alkynyl, more preferably Ci- C4-alkoxy-C2-C4-alkynyl.
  • R 3 is CCOCH3.
  • R 3 is CH2CCOCH3.
  • R 3 is Ci-C4-haloalkoxy-C2-C6- alkynyl, more preferably Ci-C4-haloalkoxy-C2-C4-alkynyl.
  • R 3 is CCOCF3.
  • I n a further special embodiment R 3 is CH2CCOCF3.
  • R 3 is
  • R 3 is CH2CCOCCI3.
  • R 3 is C3-C8-cycloalkyl-C2-C6-alkynyl, preferably C3-C6-cycloalkyl-C2-C4-alkynyl.
  • R 3 is C3-C6-halocycloalkyl-C2-C4-alkynyl, preferably C3- C8-halocycloalkyl-C2-C6-alkynyl.
  • R 3 is Cs-Cs-cycloalkyl, preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, in particular cyclopropyl or cyclobutyl.
  • R 3 is cyclopropyl.
  • R 3 is cyclobutyl.
  • R 3 is cyclopentyl.
  • I n a further special embodiment R 3 is cyclohexyl.
  • R 3 is C3-Ce-cycloalkoxy, preferably C3-C6-cycloalkoxy.
  • R 3 is C3-Cs-cycloalkyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 3 is C3-Cs-halocycloalkyl, more preferably fully or partially halogenated C3-C6-cycloalkyl.
  • R 3 is fully or partially halogenated cyclo- propyl.
  • R 3 is 1 -CI-cyclopropyl.
  • R 3 is 2-CI-cyclopropyl.
  • I n a further special embodiment R 3 is 1-F-cyclopropyl.
  • R 3 is 2-F-cyclopropyl.
  • R 3 is fully or partially halogenated cyclobutyl.
  • R 3 is 1-CI-cyclobutyl.
  • R 3 is 1 -F-cyclobutyl.
  • R 3 is C3-Ce-cycloalkyl substituted by Ci- C4-alkyl, more preferably is C3-C6-cycloalkyl substituted by Ci-C4-alkyl.
  • R 3 is 1 -CH3-cyclopropyl.
  • R 3 is C3-Cs-cycloalkyl substituted by CN, more preferably is C3-C6-cycloalkyl substituted by CN .
  • R 3 is 1 -CN- cyclopropyl .
  • R 3 is Cs-Ce-cycloalkyl-Cs-Ce-cycloalkyl, preferably C3-C6-cycloalkyl-C3-C6-cycloalkyl.
  • R 3 is cyclopropyl- cyclopropyl.
  • R 3 is Cs-Cs-cycloalkyl-Cs-Cs- halocycloalkyl, preferably C3-C6-cycloalkyl-C3-C6-halocycloalkyl.
  • R 3 is C3-C8-cycloalkyl-Ci-C4-alkyl, preferably C3-C6- cycloalkyl-Ci-C4-alkyl.
  • I n a special embodiment R 3 is CH(CH3)(cyclopropyl).
  • I n a special embodi- ment R 3 is CH2-(cyclopropyl).
  • R 3 is C3-Ce-cycloalkyl-Ci-C4-alkyl wherein the alkyl moiety can be substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein and the cycloalkyl moiety can be substituted by one, two, three or up to the maximum possible number of identical or different groups R as defined and preferably herein.
  • R 3 is C3-Cs-cycloalkyl-Ci-C4-haloalkyl, C3-C6-cycloalkyl-Ci- C4-haloalkyl.
  • R 3 is C3-C8-halocycloalkyl-Ci-C4-alkyl, C3-C6- halocycloalkyl-Ci-C4-alkyl.
  • R 3 is fully or partially halogenated cyclopro- pyl-Ci-C 4 -alkyl.
  • R 3 is 1-CI-cyclopropyl-Ci-C4-alkyl.
  • R 3 is 1 -F-cyclopropyl-Ci-C4-alkyl.
  • R 3 is NH 2 .
  • R 3 is NH(Ci-C4-alkyl). According to a specific embodiment R 3 is NH(CH3). According to a specific embodiment R 3 is NH(CH2CH3). According to a specific embodiment R 3 is NH(CH 2 CH2CH 3 ). According to a specific embodiment R 3 is NH(CH(CH 3 )2). According to a specific embodiment R 3 is NH(CH2CH2CH2CH3). According to a specific embodiment R 3 is NH(C(CH 3 ) 3 ).
  • R 3 is N(Ci-C4-alkyl)2. According to a specific embodiment R 3 is N(CH 3 )2. According to a specific embodiment R 3 is N(CH2CH3)2. According to a specific em- bodiment R 3 is N(CH2CH 2 CI-l3)2. According to a specific embodiment R 3 is N(CH(CH 3 )2)2. According to a specific embodiment R 3 is N(CH2CH2CH2CH3)2. According to a specific embodiment R 3 is NH(C(CH 3 ) 3 ) 2 .
  • R 3 is NH(C 3 -C8-cycloalkyl) preferably NH(C3-C6-cycloalkyl). According to a specific embodiment R 3 is NH(cyclopropyl). According to a specific embodiment R 3 is NH(cyclobutyl). According to a specific embodiment R 3 is NH(cyclopentyl). According to a specific embodiment R 3 is NH(cyclohexyl).
  • R 3 is N(C3-C8-cycloalkyl) 2 preferably N(C3-C6-cycloalkyl) 2 .
  • R 3 is N(cyclopropyl)2.
  • R 3 is N(cyclobutyl)2.
  • R 3 is N(cyclopentyl)2.
  • R 3 is N(cyclohexyl)2.
  • R 3 is S(0) p (Ci-C4-alkyl) wherein p is 0, 1 , 2, preferably S(0) (Ci-C4-alkyl) wherein p is 2.
  • R 3 is SO2CH3.
  • R 3 is SO2CF3.
  • said R 3 is in the 2-positon of the phenyl ring. According to one specific embodiment thereof, said R 3 is in the 3-positon of the phenyl ring. According to one further specific embodiment thereof, said R 3 is in the 4-positon of the phenyl ring. According to one specific embodiment thereof, said R 3 s in the 2, 3-positon of the phenyl ring. According to one specific embodiment thereof, said R 3 s in the 2,4-positon of the phenyl ring. According to one specific embodiment thereof, said R 3 s in the 2,5-positon of the phenyl ring.
  • said R 3 s in the 2,6-positon of the phenyl ring According to one specific embodiment thereof, said R 3 s in the 3,4-positon of the phenyl ring. According to one specific embodiment thereof, said R 3 s in the 3,5-positon of the phenyl ring. According to one specific embodiment thereof, said R 3 s in the 3,6-positon of the phenyl ring. According to one specific embodiment thereof, said R 3 s in the 2,4,6-positon of the phenyl ring.
  • P6a-6 4-F P6a-27 5-S0 2 CH 3 P6a-48 2-CI-4-F
  • P6a-10 4-CN P6a-31 5-C0 2 CH 3 P6a-52 2,4,6-F 3
  • P6a-18 4-SCH 3 P6a-39 2,4-F 2 P6a-60 5-CH 3
  • One specific embodiment relates to the inventive compounds wherein x is 1 and n is 0.
  • Y in the compounds according to the invention is, according to one embodiment, as defined in claim 1.
  • Y in the compounds according to the invention is, according to a further embodiment, a direct bond or a divalent group selected from the group consisting of -0-, -S-, SO-, -SO2-.
  • Y is -C ⁇ C-.
  • Z in the compounds according to the invention is, according to one embodiment, as defined in claim 1.
  • Z in the compounds according to the invention is, according to a further embodiment, is phenyl or a five- or six-membered heteroaryl selected from the group consisting of pyrimidin- 2-yl, pyrimidin-3-yl, pyrimidin-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazin-2-yl, pyridazin-3-yl, 1 ,3,5- triazin-2-yl and 1 ,2,4-triazin-3-yl; and wherein the phenyl is unsubstituted carries one, two, three or four independently selected radicals R 4 , and wherein the heteroaryl is unsubstitutedcarries one, two or three
  • Z is phenyl which carries one, two, three or four independently selected radicals R 4 as defined or preferably defined below.
  • Z is pyrimidin-2-yl which carries one, two, three or four independently selected radicals R 4 as defined or preferably defined below.
  • Z is pyri- din-3-yl, which carries one, two, three or four independently selected radicals R 4 as defined or preferably defined below.
  • Z is pyridin-4-yl, which carries one, two, three or four independently selected radicals R 4 as defined or preferably defined be- low.
  • Z is thiazol-2-yl, which carries one, two, three or four independently selected radicals R 4 as defined or preferably defined below.
  • x is 0. According to one further embodiment x is 1. According to one further embodiment x is 2. According to one further embodiment x is 3. According to one further embodiment x is 4.
  • R is O and Q is CH2 x is not 0.
  • R 4 in the compounds according to the invention is, according to one embodiment, as defined in claim 1.
  • R 4 in the compounds according to the invention is, according to a further embodiment, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-Cs-haloalkoxy, wherein R 4 is substituted by one, two, three or four R 4a ; wherein R 4a is independently selected from halogen, CN, NO2, OH, C1-C4- alkyl, Ci-C4-haloalkyl, Ca-Ce-cycloalkyl, Ca-Ce-halocycloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy; wherein m is 1 , 2 or 3.
  • m is 0. According to one embodiment m is 1 . According to one further embodiment m is 2. According to one further embodiment m is 3. According to one further embodiment m is 4.
  • said R 4 is in the 2-positon of the phenyl ring. According to one specific embodiment thereof, said R 4 is in the 3-positon of the phenyl ring. According to one further specific embodiment thereof, said R 4 is in the 4-positon of the phenyl ring. According to one specific embodiment thereof, said R 4 is in the 2, 3-positon of the phenyl ring. According to one specific embodiment thereof, said R 4 is in the 2,4-positon of the phenyl ring. According to one specific embodiment thereof, said R 4 is in the 2,5-positon of the phenyl ring. According to one specific embodiment thereof, said R 4 is in the 2,6-positon of the phenyl ring.
  • said R 4 is in the 3,4-positon of the phenyl ring. According to one specific embodiment thereof, said R 4 is in the 3,5-positon of the phenyl ring. According to one specific embodiment thereof, said R 4 is in the 3,6-positon of the phenyl ring. According to one specific embodiment thereof, said R 4 is in the 2,4,6-positon of the phenyl ring.
  • R 4 is halogen. According to a specific embodiment R 4 is CI. According to a further specific embodiment R 4 is F. According to a further specific embodiment R 4 is Br. According to a further specific embodiment R 4 is CN. According to a further specific embodiment R 4 is NO 2 . According to a further specific embodiment R 4 is OH. According to a further specific embodiment R 4 is SH.
  • R 4 is Ci-C6-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl.
  • R 4 is methyl.
  • R 4 is ethyl.
  • R 4 is n-propyl.
  • R 4 is i- propyl.
  • R 4 is 1 -methylpropyl.
  • R 4 is n-butyl.
  • R 4 is i-butyl.
  • R 4 is t- butyl.
  • R 4 is Ci-C6-alkyl substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 4 is Ci-C6-haloalkyl, more preferably fully or partially halo- genated methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl.
  • R 4 is CF3.
  • R 4 is CHF2.
  • R 4 is CFH2.
  • R 4 is CCI3.
  • R 4 is CHCI2.
  • R 4 is CCIH2.
  • R 4 is Ci-C6-alkyl, preferably Ci-C 4 -alkyl substituted by OH, more preferably CH 2 OH, CH 2 CH 2 OH, CH 2 CH 2 CH 2 OH, CH(CH 3 )CH 2 OH, CH 2 CH(CH 3 )OH, CH 2 CH 2 CH 2 CH 2 OH.
  • R 4 is CH 2 OH.
  • R 4 is Ci-C6-alkyl, preferably Ci-C4-alkyl substituted by CN, more preferably CH 2 CN, CH 2 CH 2 CN, CH 2 CH 2 CH 2 CN, CH(CH 3 )CH 2 CN, CH 2 CH(CH 3 )CN, CH2CH2CH2CH2CN.
  • R 4 is CH2CH2CN.
  • R 4 is CH(CH 3 )CN.
  • R 4 is Ci-C4-alkoxy-Ci-C6-alkyl, more preferably Ci-C 4 -alkoxy-Ci-C 4 -alkyl.
  • R 4 is CH 2 0CH 3 .
  • R 4 is CH 2 CH 2 OCH 3 . In a further special embodiment R 4 is CH(CH 3 )OCH 3 . In a further special embodiment R 4 is CH(CH 3 )OCH 2 CH 3 . In a further special embodiment R 4 is CH2CH2OCH2CH3. According to a further specific embodiment R 4 is Ci-C 4 -haloalkoxy-Ci-C6-alkyl, more preferably Ci-C4-alkoxy-Ci-C4-alkyl. In a special embodiment R 4 is CH 2 OCF3. In a further special embodiment R 4 is CH 2 CH 2 0CF 3 . In a further special embodiment R 4 is CH 2 0CCI 3 . In a further special embodiment R 4 is CH2CH2OCCI3.
  • R 4 is Ci-C6-alkoxy, preferably Ci-C 4 -alkoxy.
  • R 4 is OCH 3 .
  • R 4 is OCH2CH 3 .ln a further special embodiment of the invention R 4 is OCH(CH 3 )2.
  • R 4 is OCH 2 CH 2 CH 3 .
  • R 4 is OC(CH 3 ) 3 .
  • R 4 is Ci-C6-haloalkoxy, preferably Ci-C4-haloalkoxy.
  • R 4 is OCF 3 .
  • R 4 is OCHF 2 .
  • R 4 is
  • C(CH 3 ) C(CH 3 )H.
  • R 4 is C2-C6-alkenyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 4 is Ci-C4-alkoxy-C 2 -C6-alkenyl, more preferably Ci-C4-alkoxy-C2-C4-alkenyl.
  • R 4 is Ci-C4-haloalkoxy-C2-C6-alkenyl, more preferably Ci-C4-haloalkoxy-C2-C4-alkenyl.
  • R 4 is C2-C6-alkynyl, preferably CCH, CH 2 CCH, CH2CCCH 3 .
  • R 4 is CCH.
  • R 4 is CCCH 3 .
  • R 4 is CH2CCH .
  • R 4 is CH2CCCH 3 .
  • R 4 is CH 2 CCH 2 CH 3 .
  • R 4 is C2-C6-alkynyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 4 is C2-Cs-haloalkynyl, more preferably fully or partially hal- ogenated C2-Cs-alkynyl. In a special embodiment R 4 is fully or partially halogenated C2-alkynyl. In a further special embodiment R 4 is fully or partially halogenated C3-alkynyl. According to a further specific embodiment R 4 is C2-C6-alkynyl, preferably C2-C4-alkynyl, substituted by OH, more preferably, CCOH, CH2CCOH . In a special embodiment R 4 is CCOH. In a further special embodiment R 4 is CH2CCOH.
  • R 4 is Ci-C4-alkoxy-C2-C6-alkynyl, more preferably Ci-C4-alkoxy-C2-C4-alkynyl.
  • R 4 is CCOCH3.
  • R 4 is CH2CCOCH 3 .
  • R 4 is C1-C4- haloalkoxy-C2-C6-alkynyl, more preferably Ci-C4-haloalkoxy-C2-C4-alkynyl.
  • R 4 is CCOCF3.
  • R 4 is CH2CCOCF 3 .
  • R 4 is CCOCC .
  • R 4 is CH2CCOCCI3.
  • R 4 is C3-Ce-cycloalkyl-C2-C6-alkynyl, preferably C3-C6-cycloalkyl-C2- C4-alkynyl.
  • R 4 is C3-C6-halocycloalkyl-C 2 -C4-alkynyl, preferably C3-C8-halocycloalkyl-C 2 -C6-alkynyl.
  • R 4 is Cs-Cs-cycloalkyl, preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, in particular cyclopropyl or cyclobutyl.
  • R 4 is cyclopropyl.
  • R 4 is cyclobutyl.
  • R 4 is cyclopentyl.
  • R 4 is cyclohexyl.
  • R 4 is Cs-Ce-cycloalkoxy, preferably C3-C6-cycloalkoxy.
  • R 4 is O-cyclopropyl.
  • R 4 is Cs-Ce-cycloalkyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 4 is C3-Cs-halocycloalkyl, more preferably fully or partially halogenated C3-C6-cycloalkyl.
  • R 4 is fully or partially halogenated cyclopropyl.
  • R 4 is 1 -CI-cyclopropyl.
  • R 4 is 2-CI-cyclopropyl.
  • R 4 is 1-F-cyclopropyl.
  • R 4 is 2-F-cyclopropyl.
  • R 4 is fully or partially halogenated cyclobutyl.
  • R 4 is 1-CI-cyclobutyl.
  • R 4 is 1 -F-cyclobutyl. In a further special embodiment R 4 is 3,3-(CI)2-cyclobutyl. In a further special embodiment R 4 is 3,3-(F)2-cyclobutyl.According to a specific embodiment R 4 is C3-Cs-cycloalkyl substituted by Ci-C4-alkyl, more preferably is C3-C6-cycloalkyl substituted by Ci-C4-alkyl. In a special embodiment R 4 is l -CH -cyclopropyl.
  • R 4 is C3-C8- cycloalkyl substituted by CN, more preferably is C3-C6-cycloalkyl substituted by CN.
  • R 4 is 1 -CN-cyclopropyl.
  • R 4 is C3-C8- cycloalkyl-C3-C8-cycloalkyl, preferably C3-C6-cycloalkyl-C3-C6-cycloalkyl.
  • R 4 is cyclopropyl-cyclopropyl.
  • R 4 is 2-cyclopropyl-cyclopropyl.
  • R 4 is Cs-Cs-cycloalkyl-Cs-Cs-halocycloalkyl, preferably C3-C6- cycloalkyl-C3-C6-halocycloalkyl.
  • R 4 is C3-C8-cycloalkyl-Ci-C4-alkyl, preferably C3-C6- cycloalkyl-Ci-C4-alkyl.
  • R 4 is CH(CH3)(cyclopropyl).
  • R 4 is In a special embodiment R 4 is CH2-(cyclopropyl).
  • R 4 is C3-C8-cycloalkyl-Ci-C4-alkyl wherein the alkyl moiety can be substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein and the cycloalkyl moiety can be substituted by one, two, three or up to the maximum possible number of identical or different groups R b as defined and preferably herein.
  • R 4 is C3-C8-cycloalkyl-Ci-C4-haloalkyl, C3-C6-cycloalkyl-Ci- C4-haloalkyl.
  • R 4 is C3-Ce-halocycloalkyl-Ci-C4-alkyl, C3-C6- halocycloalkyl-Ci-C4-alkyl.
  • R 4 is fully or partially halogenated cyclopro- pyl-Ci-C4-alkyl.
  • R 4 is 1-CI-cyclopropyl-Ci-C4-alkyl.
  • R 4 is 1 -F-cyclopropyl-Ci-C4-alkyl.
  • R 4 is NH2. According to one another embodiment R 4 is NH(Ci-C4-alkyl). According to a specific embodiment R 4 is NH(CH3). According to a specific embodiment R 4 is NH(CH2CH3). According to a specific embodiment R 4 is NH(CH 2 CH 2 CH3). According to a specific embodiment R 4 is NH(CH(CH 3 )2). According to a specific embodiment R 4 is NH(CH2CH2CH2CH3). According to a specific embodi- ment R 4 is NH(C(CH 3 ) 3 ).
  • R 4 is N(Ci-C4-alkyl)2. According to a specific embodiment R 4 is N(CH3)2. According to a specific embodiment R 4 is N(CH2CH3)2. According to a specific embodiment R 4 is N(CH2CH 2 CH 3 )2. According to a specific embodiment R 4 is N(CH(CH 3 )2)2. According to a specific embodiment R 4 is N(CH2CH2CH2CH3)2. According to a specific embodiment R 4 is NH(C(CH 3 ) 3 ) 2 .
  • R 4 is NH(C3-C8-cycloalkyl) preferably NH(C3-C6-cycloalkyl). According to a specific embodiment R 4 is NH(cyclopropyl). According to a specific embodiment R 4 is NH(cyclobutyl). According to a specific embodiment R 4 is NH(cyclopentyl). According to a specific embodiment R 4 is NH(cyclohexyl).
  • R 4 is N(C3-C8-cycloalkyl) 2 preferably N(C3-C6-cycloalkyl) 2 .
  • R 4 is N(cyclopropyl)2.
  • R 4 is N(cyclobutyl)2.
  • R 4 is N(cyclopentyl)2.
  • R 4 is N(cyclohexyl)2.
  • R 4 is S(0) p (Ci-C4-alkyl) wherein p is 0, 1 , 2, preferably S(0) (Ci-C4-alkyl) wherein p is 2.
  • R 4 is SO 2 CH3.
  • R 4 is SO2CF3.
  • Particularly preferred embodiments of R 4 m according to the invention are in Table X below, where- in each line of lines X1 -1 to X1 -145 corresponds to one particular embodiment of the invention, wherein X1-1 to X1-145 are also in any combination a preferred embodiment of the present invention
  • Z-R 4 m are in Table Y below, wherein each line of lines Y-1 to Y-145 corresponds to one particular embodiment of the invention, wherein Y-1 to Y-145 are also in any combination a preferred embodiment of the present invention
  • Z-R 4 m Particularly preferred embodiments of Z-R 4 m according to the invention are in Table Z below, wherein each line of lines Z-1 to Z-109 corresponds to one particular embodiment of the invention, wherein Z-1 to Z-109 are also in any combination a preferred embodiment of the present invention Table Z
  • R 5 and R 6 in the compounds according to the invention are independently of another, according to one embodiment, as defined in claim 1.
  • R 5 and R 6 in the compounds according to the invention are independently of another, according to a further embodiment, H, according to one embodiment, both are H.
  • R 5 and R 6 in the compounds according to the invention are independently of another halogen.
  • R 5 and R s are independently CI.
  • R 5 and R 6 are independently F.
  • R 5 and R s are independently Br.
  • R 5 and R 6 are independently CN.
  • R 5 and R 6 are independently NO2.
  • R 5 and R 6 are independently OH.
  • R 5 and R 6 are independently SH.
  • R 5 is H and R 6 is CI.
  • R 5 is H and R 6 is Br.
  • R 5 is H and R 6 is F.
  • R 5 and R 6 are independently selected from Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Ce-cycloalkyl, wherein the R 1 are in each case unsubstituted or are substituted by R a and/or R b as defined and preferably herein.
  • R 5 and R 6 are independently selected from Ci-C3-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the R 5 and R 6 are inde- pendently in each case unsubstituted or are substituted by R a and/or R b as defined and preferably herein.
  • R 5 and R 6 are independently Ci-C6-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl.
  • R 5 and R 6 are independently methyl.
  • R 5 and R 6 are independently ethyl.
  • R 5 and R 6 are independently n-propyl.
  • R 5 and R 6 are independently i-propyl.
  • R 5 and R 6 are independently 1- methylpropyl.
  • R 5 and R 6 are independently n-butyl.
  • R 5 and R 6 are independently i-butyl.
  • R 5 and R 6 are independently t-butyl.
  • R 5 is H and R 6 is CH3. In a further special embodiment R 5 is H and R 6 is CH2CH3. In a further special embodiment R 5 is H and R 6 is CH2CH2CH3. In a further special embodiment R 5 is H and R 6 is CH(CH3)2. In a further special embodiment R 5 is CH3 and R 6 is CH3. In a further special embodiment R 5 is CH2CH3 and R 6 is CH2CH3.
  • R 5 and R 6 are independently Ci-C 6 -alkyl substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 5 and R 5 are independently Ci-C6-haloalkyl, more preferably fully or partially halogenated methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl.
  • R 5 and R 6 are independently CF3.
  • R 5 and R 6 are independently CHF2.
  • R 5 and R 6 are independently CFH2.
  • R 5 and R 6 are independently CCI3.
  • R 5 and R 6 are independently CHCI2.
  • R 5 and R 6 are independently CCIH2.
  • R 5 and R 6 are independently Ci-C s -alkyl, preferably Ci-C 4 -alkyl substituted by OH, more preferably CH 2 OH, CH 2 CH 2 OH, CH 2 CH 2 CH 2 OH, CH(CH 3 )CH 2 OH, CH 2 CH(CH 3 )OH, CH2CH2CH2CH2OH.
  • R 5 and R 6 are independently CH 2 OH.
  • R 5 and R 6 are independently CH 2 CH 2 OH.
  • R 5 and R 6 are independently Ci-C 6 -alkyl, preferably Ci-C 4 -alkyl substituted by CN, more preferably CH 2 CN, CH 2 CH 2 CN, CH 2 CH 2 CH 2 CN,
  • R 5 and R 6 are independently CH2CH2CN. In a further special embodiment R 5 and R 6 are independently
  • R 5 and R 6 are independently C 1 -C4- alkoxy-Ci-C6-alkyl, more preferably Ci-C4-alkoxy-Ci-C4-alkyl.
  • R 5 and R 6 are independently CH2OCH3.
  • R 5 and R 6 are independently CH2CH2OCH3.
  • R 5 and R 6 are independently CH(CH 3 )OCH 3 .
  • R 5 and R 6 are independently CH(CH3)OCH2CH3.
  • R 5 and R 6 are independently CH2CH2OCH2CH3.
  • R 5 and R 6 are independently Ci-C4-haloalkoxy-Ci-C6-alkyl, more preferably C1-C4- alkoxy-Ci-C4-alkyl.
  • R 5 and R 6 are independently CH 2 OCF3.
  • R 5 and R 6 are independently CH2CH2OCF3.
  • R 5 and R 6 are independently CH2OCCI3.
  • R 5 and R 6 are independently CH2CH2OCCI3.
  • R 5 and R 6 are independently Ci-C6-alkoxy, preferably Ci- C 4 -alkoxy.
  • R 5 and R 6 are independently OCH3.
  • R 5 and R 6 are independently OCH 2 CH3.
  • R 5 and R 6 are independently OCH(CH3)2.
  • R 5 and R 6 are independentlyOChbCI-bCHs.
  • R 5 and R 6 are independently OC(CH3)3.
  • R 5 and R 6 are independently CH2CI- CH2.
  • R 5 and R 6 are independently C 2 -C6-alkenyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 5 and R s are independently C2-C6-haloalkenyl, more preferably fully or partially halogenated C2-C6-alkenyl.
  • R 5 and R 6 are inde- pendently fully or partially halogenated C2-alkenyl.
  • R 5 and R 6 are independently fully or partially halogenated C 3 -alkenyl.
  • R 5 and R 6 are independently
  • R 5 and R 6 are independently C 2 -C 6 -alkynyl, preferably CCH, CH2CCH, CH 2 CCCH 3 .
  • R 5 and R 6 are independently CCH.
  • R 5 and R 6 are independently CCCH3.
  • R 5 and R 6 are independently CCCH(CH3)2.
  • I n a further special embodiment R 5 and R 6 are independently CCC(CH3)3.
  • I n a further special embodiment R 5 and R 6 are independently CH2CCH .
  • R 5 and R 6 are independently CH2CCCH3.
  • R 5 and R 6 are independently CC(C2H 5 )
  • I n a further special embodiment R 5 and R 6 are independently CH2CCH2CH3.
  • R 5 and R 6 are independently C2-C6-alkynyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 5 and R 5 are independently C2-C6-haloalkynyl, more preferably fully or partially halogenated C2-C6-alkynyl.
  • R 5 and R 6 are independently fully or partially halogenated C2-alkynyl.
  • I n a further special embodiment R 5 and R 6 are independently fully or partially halogenated C3-alkynyl.
  • R 5 and R 6 are independently CCCI.
  • R 5 and R 6 are independently CCBr.
  • R 5 and R 6 are independently CC-I .
  • R 5 and R 6 are independently CH2-CCCI.
  • I n a further special embodiment R 5 and R s are independently CH2-CCBr. I n a further special embodiment R 5 and R 5 are independently CH2-CC-I . According to a further specific embodiment R 5 and R 6 are independently C2-C 6 -alkynyl, preferably C2-C4- alkynyl, substituted by OH . In a special embodiment R 5 and R 6 are independently CC- C(OH)(CH3)2. According to a further specific embodiment R 5 and R 6 are independently C1-C4- alkoxy-C2-C6-alkynyl, more preferably Ci-C4-alkoxy-C2-C4-alkynyl. I n a special embodiment R 5 and R 6 are independently CCOCH3.
  • R 5 and R 6 are independently CC- CH2-OCH3.
  • R 5 and R 6 are independently CC-C(OCH 3 )(CH 3 )2.
  • R 5 and R 6 are independently CH2CCOCH3.
  • R 5 and R 6 are independently Ci-C4-haloalkoxy-C2-C 6 -alkynyl, more preferably C1-C4- haloalkoxy-C2-C4-alkynyl.
  • R 5 and R 6 are independently CC- CH2OCCI3.
  • R 5 and R 6 are independently CC-CH2OCF3 According to a further specific embodiment R 5 and R 6 are independently C3-C8-cycloalkyl-C2-C6-alkynyl, preferably C3-C 6 -cycloalkyl-C2-C4-alkynyl. In a special embodiment R 5 and R 6 are independently CC(C3H 5 ). I n a special embodiment R 5 and R 6 are independently CC(C4H 7 ). I n a special embodiment R 5 and R 6 are independently CCCH2(C3H5). I n a special embodiment R 5 and R 6 are independently CC-CH2-C4H7).
  • R 5 and R 6 are independently C3-C6-halocycloalkyl-C2-C4-alkynyl, preferably C3-C8-halocycloalkyl-C2-C6-alkynyl.
  • I n a special embodiment R 5 and R 6 are independently CC(C3H4CI) .
  • I n a special embodiment R 5 and R 6 are independently CC(C3H4F).
  • I n a special embodiment R 5 and R s are independently CC(C4H6CI).
  • R 5 and R 6 are independently CC(C4HeF).
  • R 5 and R 6 are independently Cs-Ce-cycloalkyl, preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, in particular cyclopropyl or cyclobutyl.
  • I n a special embodiment R 5 and R 6 are independently cyclopropyl.
  • R 5 and R 6 are independently cyclobutyl.
  • I n a further special embodiment R 5 and R 6 are independently cyclopentyl.
  • R 5 and R 6 are independently cyclohexyl.
  • R 5 and R 6 are independently C3-Cs-cycloalkyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 5 and R 6 are independently C3-Ce-halocycloalkyl, more preferably fully or partially halogenated C3-C 6 -cycloalkyl.
  • R 5 and R 6 are independently fully or partially halogenated cyclopropyl.
  • R 5 and R 6 are independently 1-CI-cyclopropyl.
  • R 5 and R 6 are independently 2- Cl-cyclopropyl.
  • R 5 and R 6 are independently 1-F-cyclopropyl.
  • R 5 and R 6 are independently 2-F-cyclopropyl.
  • R 5 and R 6 are independently fully or partially halogenated cyclobutyl.
  • R 5 and R 6 are independently 1 -CI-cyclobutyl.
  • R 5 and R 6 are independently 1-F-cyclobutyl.
  • R 5 and R 6 are independently 1 -CI-cyclobutyl.
  • R 5 and R 6 are independently 1-F-cyclobutyl.
  • R 5 and R 6 are independently 1 -CI-cyclo
  • R 5 and R 6 are independently C3-C8-cycloalkyl substituted by Ci-C4-alkyl, more preferably is C3-C 6 -cycloalkyl substituted by Ci- C4-alkyl.
  • R 5 and R 6 are independently 1-CH3-cyclopropyl.
  • R 5 and R 6 are independently 2-CH3-cyclopropyl.
  • R 5 and R 6 are independently l-CH -cyclobutyl.
  • R 5 and R 6 are independently 2-CH3-cyclobutyl.
  • R 5 and R s are independently
  • R 5 and R 6 are independently 3,3-(CH3) 2 - cyclobutyl.
  • R 5 and R 6 are independently Cs-Cs-cycloalkyl substituted by CN, more preferably is C3-C 6 -cycloalkyl substituted by CN.
  • R 5 and R 6 are independently 1-CN-cyclopropyl.
  • R 5 and R 6 are in- dependently 2-CN-cyclopropyl.
  • R 5 and R 6 are independently C3-C8-cycloalkyl-C3-C8-cycloalkyl, preferably C3-C6-cycloalkyl-C3-C6-cycloalkyl.
  • R 5 and R 6 are independently 1 -cyclopropyl-cyclopropyl.
  • R 5 and R 6 are independently 2-cyclopropyl-cyclopropyl.
  • R 5 and R 6 are independently Cs-Cs-cycloalkyl-Cs-Cs-halocycloalkyl, preferably C3-C6- cycloalkyl-C3-C 6 -halocycloalkyl.
  • R 5 and R 6 are independently C3-C8-cycloalkyl-Ci-C4-alkyl, preferably C3-C 6 -cycloalkyl-Ci-C4-alkyl.
  • R 5 and R 6 are independently CH(CH3)(cyclopropyl).
  • R 5 and R 6 are independently CH2-(cyclopropyl).
  • R 5 and R 6 are independently CH(CH3)(cyclobutyl).
  • R 5 and R 6 are independently CH 2 -(cyclobutyl).
  • R 5 and R 6 are independently CH2CH2-(cyclopropyl).
  • R 5 and R 6 are independently CH2CH2- (cyclobutyl).
  • R 5 and R 6 are independently C3-Cs-cycloalkyl-Ci-C4- alkyl wherein the alkyl moiety can be substituted by one, two, three or up to the maximum possi- ble number of identical or different groups R a as defined and preferably herein and the cycloalkyl moiety can be substituted by one, two, three or up to the maximum possible number of identical or different groups R b as defined and preferably herein.
  • R 5 and R s are independently C3-C8-cycloalkyl-Ci-C4- haloalkyl, C3-C s -cycloalkyl-Ci-C4-haloalkyl.
  • R 5 and R 6 are independently C3-Ce-halocycloalkyl-Ci-C4-alkyl, C3-C 6 -halocycloalkyl-Ci-C4-alkyl.
  • R 5 and R 6 are independently fully or partially halogenated cyclopropyl-Ci-C4-alkyl.
  • R 5 and R 6 are independently 1 -CI-cyclopropyl-Ci-C4-alkyl. In a further special embodiment R 5 and R 6 are independently 1 -F-cyclopropyl-Ci-C4-alkyl. In a further very special embodiment R 5 and R 6 are independently Ch -l -CI-cyclopropyl. In a further very special embodiment R 5 and R 6 are independently CH2-1 -F-cyclopropyl. In a further very special embodiment R 5 and R 6 are independently CH(CH3)-1-CI-cyclopropyl. In a further very special embodiment R 5 and R 6 are independently C(CH3)2-1-F-cyclopropyl. In a further very special embodiment R 5 and R 6 are independently CH2-I -F-cyclobutyl. In a further very special embodiment R 5 and R 6 are independently Chb-l -CI-cyclobutyl.
  • R 5 and R 6 are independently phenyl.
  • R 5 and R 6 are independently phenyl substituted by one, two, three or up to the maximum possible number of identical or different groups R b as defined and preferably herein.
  • R 5 and R s are independently phenyl substituted by one, two or three halogen atoms, preferably by one, two or three CI or F.
  • R 5 and R 6 are independently 2-CI-phenyl.
  • R 5 and R 6 are independently 2- F-phenyl.
  • R 5 and R 6 are independently 4-CI-phenyl.
  • R 5 and R 6 are independently 4-CI-phenyl.
  • R 5 and R 6 are independently 4-F-phenyl.
  • R 5 and R 6 are independently 4-F-phenyl.
  • R 5 and R 6 are independently 2,4-Cl2- phenyl.
  • R 5 and R 6 are independently 2,4-F2-phenyl. In a further special embodiment R 5 and R 6 are independently 2-CI-4-F-phenyl. In a further special embodi- ment R 5 and R 6 are independently 2-F-4-CI-phenyl. In a further special embodiment R 5 and R 6 are independently 2,4,6-Cl3-phenyl. In a further special embodiment R 5 and R 6 are independently 2,4,6-Fs-phenyl.
  • R 5 and R s are independently phenyl substituted by one, two or three CN or OH groups.
  • R 5 and R 6 are independently 2-OH-phenyl.
  • R 5 and R 6 are independently 4-OH-phenyl.
  • R 5 and R 6 are independently 2,4-OH2-phenyl.
  • R 5 and R 6 are independently 2,4,6-OH 3 -phenyl.
  • R 5 and R s are independently phenyl substituted by one, two or three Ci-C4-alkyl or Ci-C4-haloalkyl groups, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl or CF 3 , CHF 2 , CFH 2 , CCI 3 , CHCI 2 , CCIH 2 .
  • R 5 and R 6 are independently 2-CH3-phenyl.
  • R 5 and R 6 are independently 2-CF3- phenyl.
  • R 5 and R 6 are independently 4-CH3-phenyl.
  • R 5 and R 6 are independently 4-CF3-phenyl.
  • R 5 and R 6 are independently phenyl substituted by one, two or three Ci-C4-alkoxy or Ci-C4-haloalkoxy groups, preferably preferably Ci-C4-alkoxy, more preferably CH3O, CH3CH2O, CH3CH2CH2O, CH 2 (CH 3 )CH 2 0, CH 3 CH(CH 3 )0, CH3CH2CH2CH2O, CF 3 0, CCI3O.
  • R 5 and R 6 are independently 2-CH30-phenyl.
  • R 5 and R 6 are independently 2-CF30-phenyl.
  • R 5 and R 6 are independently 4-CH30-phenyl.
  • R 5 and R 6 are independently 4-CF 3 0-phenyl.
  • R 5 and R 6 are independently phenyl-CrC 4 -alkyl, preferably phenyl- Ci-C 2 -alkyl.
  • R 5 and R s are independently benzyl.
  • R 5 and R 6 are independently phenyl-Ci-C4-alkyl therein the alkyl moiety can be substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein, in particular selected from halogen, in particular CI and F, Ci-C4-alkoxy, in particular OCH3, Ci-C4-alkyl, in particular CH3 or C2H 5 , and CN, and phenyl can be substituted by one, two, three or up to the maximum possible number of identical or different groups R b as defined and preferably herein in particular selected from halogen, in particular CI and F, Ci-C4-alkoxy, in particular OCH3, Ci-C4-alkyl, in particular CH3 or C 2 H 5 , and CN.
  • R a as defined and preferably herein, in particular selected from halogen, in particular CI and F, Ci-C4-alkoxy, in particular OCH3, Ci-C4-alky
  • R 5 and R 6 are independently CH 2 -(4-CI)-phenyl. In a further special embodiment R 5 and R 6 are independently CH2-(4-CH3)-phenyl. In a further special embodiment R 5 and R 6 are independently CH 2 -(4-OCH3)-phenyl. In a further special embodiment R 5 and R 6 are independently CH 2 -(4-F)-phenyl. In a further special embodiment R 5 and R 6 are independently CH 2 -(2,4-Cl 2 )-phenyl. In a further special embodiment R 5 and R 6 are independently CH 2 -(2,4-F 2 )-phenyl.
  • R 5 and R 6 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six- or seven- membered carbocycle.
  • R 5 and R 6 form cyclopropyl.
  • R 5 and R 6 form cyclobutyl.
  • R 5 and R 6 form cyclo- penyl.
  • R 5 and R 6 form cyclohexyl. Further preffered are cyclo- pentenyl, cyclopentadienyl and cyclohexenyl.
  • Preferred are halogen such as CI, Br, F, Ci-C6-haloalkyl and Ci-C6-alkoxy.
  • R 5 and R 6 together with the carbon atom to which they are bound form a a saturated or partially unsaturated three-, four-, five-, six- or seven- membered heterocycle, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbo- or heterocycle is unsubstituted or carries one, two, three or four substituents independently selected from halogen, CN, NO2, OH, SH, NH2, d-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 5 -haloalkoxy, Ci-C 6 -alkylthio, Ci-C 6 - haloalkylthio, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy; and wherein one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C
  • R 5 and R s form cyclopropanone, cyclopentanone, cyclopropanethi- one, cyclopentanethione, 5-oxazolone, cyclohexane-1 ,4-dione, cyclohexane-1 ,4-dithione, cy- clohex-2-ene-1 ,4-dione or cyclohex-2-ene-1 ,4-dithione.
  • Further preffered are oxirane, aziridine, thiirane, oxetane, azetidine, thiethane, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl,
  • C* CCl2.
  • C * CHBr.
  • R 7 in the compounds according to the invention is, according to one embodiment, as defined in claim 1.
  • R 7 in the compounds according to the invention is, according to a further embodiment, C1-C6- alkyl or C3-C6-cycloalkyl, wherein R 7 is substituted by one, two, three or four R 7a ; wherein R 7a is independently selected from halogen.
  • o is 0. According to one further embodiment o is 1. According to one further embodiment o is 2. According to still one further embodiment o is 3. According to one further embodiment o is 4.
  • R 7 is Ci-C6-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl.
  • R 7 is methyl.
  • R 7 is ethyl.
  • R 7 is n-propyl.
  • R 7 is i- propyl.
  • R 7 is 1 -methylpropyl.
  • R 7 is n-butyl.
  • R 7 is i-butyl.
  • R 7 is t- butyl.
  • R 4 is Ci-C6-alkyl substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 7 is Ci-C6-haloalkyl, more preferably fully or partially halo- genated methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl.
  • R 7 is CF3.
  • R 7 is CH F2.
  • R 7 is CFH 2 .
  • R 7 is CCI3.
  • R 7 is CHCI2.
  • R 7 is CCIH2.
  • R 7 is Ci-C6-alkyl, preferably d-C z-alkyl substituted by OH, more preferably CH 2 OH, CH 2 CH 2 OH, CH 2 CH 2 CH 2 OH, CH(CH 3 )CH 2 OH, CH 2 CH(CH 3 )OH, CH2CH2CH2CH2OH .
  • R 7 is CH 2 OH.
  • R 7 is Ci-C 7-alkoxy-Ci-C6-alkyl, more preferably C1-C 7-alkoxy-Ci-C 7-alkyl.
  • R 7 is CH2OCH3.
  • R 7 is CH2CH2OCH3. In a further special embodiment R 7 is CH(CH3)OCH3. In a further special em- bodiment R 7 is CH(CH 3 )OCH 2 CH 3 . In a further special embodiment R 7 is CH2CH2OCH2CH3.
  • R 7 is C2-C6-alkenyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 7 is C2-C6-haloalkenyl, more preferably fully or partially halogenated C2-C6-alkenyl.
  • R 7 is fully or partially halogenated C2-alkenyl.
  • R 7 is fully or partially halogenated C3-alkenyl.
  • R 7 is Ci-C 7-alkoxy-C2-C6-alkenyl, more preferably Ci-C 7-alkoxy-C2-C 7-alkenyl.
  • R 7 is
  • R 7 is C2-C6-alkynyl, preferably CCH, CH2CCH,
  • R 7 is CCH. in a further special embodiment R 7 is CCCH3. In a further special embodiment R 7 is CH2CCH. In a further special embodiment R 7 is CH2CCCH3. In a further special embodiment R 7 is CH2CCH2CH3.
  • R 7 is C2-C6-alkynyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 7 is C2-C6-haloalkynyl, more preferably fully or partially halogenated C2-Cs-alkynyl. In a special embodiment R 7 is fully or partially halogenated C2-alkynyl. In a further special embodiment R 7 is fully or partially halogenated C3-alkynyl. According to a further specific embodiment R 7 is C2-C6-alkynyl, preferably C2-C 7 -alkynyl, substituted by OH, more preferably, CCOH, CH2CCOH . In a special embodiment R 7 is CCOH. In a further special embodiment R 7 is CH2CCOH .
  • R 7 is C1-C 7-alkoxy-C2-C6-alkynyl, more preferably Ci-C 7-alkoxy-C2-C 7-alkynyl.
  • R 7 is CCOCH3.
  • R 7 is CH2CCOCH3.
  • R 7 is C 3 -C8-cycloalkyl, preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, in particular cyclopropyl or cyclobutyl.
  • R 7 is cyclopropyl.
  • R 7 is cyclobutyl.
  • R 7 is cyclopentyl.
  • R 7 is cyclohexyl.
  • R 7 is C3-Ce-cycloalkoxy, preferably C3-C6-cycloalkoxy.
  • R 7 is O-cyclopropyl.
  • R 7 is C3-Ce-cycloalkyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein.
  • R 7 is C3-C8-halocycloalkyl, more preferably fully or partially halogenated C 3 -C6-cycloalkyl.
  • R 7 is fully or partially halogenated cyclopropyl.
  • R 7 is 1-CI-cyclopropyl.
  • R 7 is 2-CI-cyclopropyl.
  • R 7 is 1 -F-cyclopropyl.
  • R 7 is 2-F-cyclopropyl.
  • R 7 is fully or partially halogenated cyclobutyl.
  • R 7 is 1 -CI-cyclobutyl.
  • R 7 is 1-F-cyclobutyl. In a further special embodiment R 7 is 3,3-(CI)2-cyclobutyl. In a further special embodiment R 7 is 3,3-(F)2-cyclobutyl.
  • R 71 and R 72 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six- or seven- membered carbocycle.
  • R 5 and R 6 form cyclopropyl.
  • R 5 and R 6 form cyclobutyl.
  • R 5 and R 6 form cyclo- penyl.
  • R 5 and R 6 form cyclohexyl. Further preffered are cyclo- pentenyl, cyclopentadienyl and cyclohexenyl.
  • R 71 and R 72 form cyclopropanone, cyclopentanone, cyclopro- panethione, cyclopentanethione, 5-oxazolone, cyclohexane-1 ,4-dione, cyclohexane-1 ,4- dithione, cyclohex-2-ene-1 ,4-dione or cyclohex-2-ene-1 ,4-dithione.
  • oxirane aziridine, thiirane, oxetane, azetidine, thiethane, 2-tetrahydrofuranyl, 3- tetrahydrofuranyl, 2-tetrahydrothienyl and 3-tetrahydrothienyl.
  • the present invention relates to compounds of the formulae I. A to I.H, each of them representing a specific embodiment of the invention ,wherein the variables are defined and preferably defined as described for compounds I herein: (Exemplary numbering of the carbon atoms can be found in compound I. A)
  • the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
  • the present invention relates to compounds of the formulae II.A to I I.H, each of them representing a specific embodiment of the invention ,wherein the variables are defined and preferably defined as described for compounds I herein:
  • the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
  • the present invention relates to compounds of the formulae 111.A to III. I— I , each of them representing a specific embodiment of the invention ,wherein the variables are defined and preferably defined as described for compounds I herein:
  • I.C.A2.B1 to I.C.A2.B2340 compounds I.D.A2.B1 to I.D.A2.B2340; compounds I.E.A2.B1 to I.E.A2.B2340; compounds I.F.A2.B1 to I.F.A2.B2340; compounds I.G.A2.B1 to I.G.A2.B2340; compounds I.H.A2.B1 to I.H.A2.B2340).
  • Table 6a-l Compounds of the formula I.A, I.B. I.C, I.D, I.E, I.F, I.G, I.H in which the combination of R 5 and R 6 corresponds to line A-6 of Table A and the meaning for the combination of (R 3 ) n , (R 4 )m, R 71 and R 72 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A6.B1 to I.A.A6.B2340, compounds I.B.A6.B1 to I.B.A6.B2340; compounds I.C.A6.B1 to I.C.A6.B2340; compounds I.D.A6.B1 to I.D.A6.B2340; compounds I.E.A6.B1 to I.E.A6.B2340; compounds I.F.A6.B1 to I.F.A6.B2340; compounds I.G.A6.B1 to I.G
  • I.C.A8.B1 to I.C.A8.B2340 compounds I.D.A8.B1 to I.D.A8.B2340; compounds I.E.A8.B1 to I.E.A8.B2340; compounds I.F.A8.B1 to I.F.A8.B2340; compounds I.G.A8.B1 to I.G.A8.B2340; compounds I.H.A8.B1 to I.H.A8.B2340).
  • Table 13a-lll Compounds of the formula III A 1M B. III.C, III.D, III.E, III.F, III.G, III.H in which the combination of 5 and R 6 corresponds to line A-13 of Table A and the meaning for the combination of (R 3 ) n , (R 4 )m, R 71 and R 72 for each individual compound corresponds in each case to one line of Table B (compounds III.A.A13.B1 to III.A.A13.B2340, compounds III.B.A13.B1 to III.B.A13.B2340; com- pounds III.C.A13.B1 to III.C.A13.B2340; compounds III.D.A13.B1 to III.D.A 3.B2340; compounds III.E.A13.B1 to I II .E.A13.B2340; compounds III.F.A13.B1 to III.F.A13.B2340; compounds III.G.A13.B1 to III
  • I.C.A1.Bb1 to I.C.A1.Bb260 compounds I.D.A1.Bb1 to I.D.A1.Bb260; compounds I.E.A1.BM to I.E.A1.Bb260; compounds I.F.A1.Bb1 to I.F.A1.Bb260; compounds I.G.A1 .Bb1 to I.G.A1.Bb260; compounds I.H.A1 .Bb1 to I.H.A1.Bb260).
  • I.C.A7.Bb1 to I.C.A7.Bb260 compounds I.D.A7.Bb1 to I.D.A7.Bb260; compounds I.E.A7.Bb1 to I.E.A7.Bb260; compounds I.F.A7.Bb1 to I.F.A7.Bb260; compounds I.G.A7.Bb1 to I.G.A7.Bb260; compounds I.H.A7.Bb1 to I.H.A7.Bb260).
  • the present invention relates to compounds of the formulae IV.A to IV.R, each of them representing a specific embodiment of the invention, wherein the variables are defined and preferably defined as described for compounds I herein:
  • the present invention relates to compounds of the formulae V.A to V.R, each of them representing a specific embodiment of the invention, wherein the variables are defined and preferably defined as described for compounds I herein:
  • the present invention relates to compounds of the formulae III.A to III. F , each of them representing a specific embodiment of the invention, wherein the variables are defined and preferably defined as described for compounds I herein:
  • Table 1 a-IV Compounds of the formula IV.A, IV.B, IV.C, IV.D, IV.E, IV.F, IV.G, IV.H, IV.I, IV.J, IV.K, IV.L, IV.M, IV.N, IV.O, IV.P, IV.Q, IV.R in which the combination of R 71 and R 72 corresponds to line C-
  • IV.J.C10.P180 compounds IV.K.C10.P1 to IV.K.C10.P180; compounds IV.L.C10.P1 to IV.LC10.P180; compounds IV.M.C10.P1 to IV.M.C10.P180; compounds IV.N.C10.P1 to IV.N.C10.P180; compounds IV.O.C10.P1 to IV.O.C10.P180; compounds IV.P.C10.P1 to IV.P.C10.P180; compounds IV.Q.C10.P1 to IV.Q.C10.P180; compounds IV.R.C10.P1 to IV. R.C10.P180;).
  • V. O, V.P, V.Q, V.R in which the combination of R 71 and R 72 corresponds to line C-1 of Table C and the meaning for (R 3 ) n for each individual compound corresponds in each case to one line of
  • Table 8a-V Compounds of the formula V.A, V.B, V.C, V.D, V.E, V.F, V.G, V.H, V.I, V.J, V.K, V.L, V.M, V.N, V.O, V.P, V.Q, V.R in which the combination of R 71 and R 72 corresponds to line C-8 of Table C and the meaning for (R 3 ) n for each individual compound corresponds in each case to one line of Table P (compounds V.A.C8.P1 to V.A.C8.P180; compounds V.B.C8.P1 to V.B.C8.P180; com- pounds V.C.C8.P1 to V.C.C8.P180; compounds V.D.C8.P1 to V.D.C8.P180; compounds
  • V.O.C10.P180 compounds V.P.C10.P1 to V.P.C10.P180; compounds V.Q.C10.P1 to
  • V. Q.C10.P180 compounds V.R.C10.P1 to V.R.C10.P180.

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Abstract

La présente invention concerne de nouveaux triazoles et imidazoles substitués et leur utilisation en tant que fongicides. La présente invention concerne de nouveaux composés triazoles et imidazoles substitués de formule I telle que définie dans la description, et les N-oxydes, ainsi que les sels de ceux-ci, leur préparation et des intermédiaires pour leur préparation. La présente invention concerne en outre l'utilisation de ces composés pour lutter contre les champignons nuisibles et des semences enrobées avec au moins un tel composé et également des compositions comprenant au moins un tel composé.
PCT/EP2013/076276 2012-12-19 2013-12-11 Nouveaux triazoles et imidazoles substitués et leur utilisation en tant que fongicides WO2014095534A1 (fr)

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Cited By (4)

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US9815798B2 (en) 2014-03-26 2017-11-14 Basf Se Substituted [1,2,4]triazole and imidazole compounds as fungicides
US10053432B2 (en) 2013-12-12 2018-08-21 Basf Se Substituted [1,2,4]triazole and imidazole compounds
US10112913B2 (en) 2014-05-13 2018-10-30 Basf Se Substituted [1,2,4]triazole and imidazole compounds as fungicides
US10450279B2 (en) 2014-06-06 2019-10-22 Basf Se Substituted [1,2,4]triazole compounds

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