WO2008107398A2 - Pyrazine compounds - Google Patents

Pyrazine compounds Download PDF

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WO2008107398A2
WO2008107398A2 PCT/EP2008/052515 EP2008052515W WO2008107398A2 WO 2008107398 A2 WO2008107398 A2 WO 2008107398A2 EP 2008052515 W EP2008052515 W EP 2008052515W WO 2008107398 A2 WO2008107398 A2 WO 2008107398A2
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cio
alkyl
combination
group
formula
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PCT/EP2008/052515
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French (fr)
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WO2008107398A3 (en
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Jochen Dietz
Marianna Vrettou
Bernd Müller
Jens Renner
Sarah Ulmschneider
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to novel pyrazine compounds, to their use for controlling harmful fungi, to their use in the treatment of cancer and to fungicidal or pharmaceutical compositions comprising at least one of these compounds as active component.
  • Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer.
  • WO 2006/089060 describes pyrazine derivatives which carry in the 2-position an oxygen, sulphur or nitrogen atom bound via a double bond.
  • the 6-position carries an optionally substituted aliphatic, cycloaliphatic, aromatic or heteroaromatic radical and the 3-position a heterocyclic or heteroatom-containing group.
  • the compounds are used for combating harmful fungi.
  • the present invention relates pyrazine compounds of the formula I, N- oxides or agriculturally useful salts thereof
  • A is O, S or NR 10 ;
  • R 2 is a carboaromatic or heteroaromatic group selected from phenyl, benzyl, naphthyl, a 5- or 6-membered heteroaromatic radical, where the heteroaromatic radical contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members, and phenyl fused to a saturated or unsaturated aromatic or non-aromatic 5- or 6-membered heterocyclic ring, where the heterocyclic ring contains 1 , 2 or 3 heteroatoms selected from the group consisting of O, S and N as ring members and may furthermore contain 1 or 2 CO groups as ring members, where the carboaromatic or heteroaromatic group carries one substituent L 1 and 1 , 2, 3 or 4 identical or different substituents L 2 ;
  • R 3 is hydrogen, halogen, hydroxyl, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C 2 -Cio-alkenyl, C 2 -Cio-haloalkenyl, C 2 -Cio-alkynyl, C 2 -Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-C10- halocycloalkyl, Ci-Cio-alkoxy, Ci-Cio-haloalkoxy , Ci-Cio-alkylthio, C1-C10- haloalkylthio, Ci-Cio-alkylsulfinyl, Ci-Cio-haloalkylsulfinyl, Ci-Cio-alkylsulfonyl, Ci-Cio-haloalkylsulfonyl, Ci-C 4 -alkoxy-Ci-C 4
  • R 4 is halogen, cyano, SCN, hydroxyl, mercapto, N3, Ci-C6-alkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, d-C ⁇ -alkoxy, Cs-Cs-alkenyloxy, Cs-Cs-alkynyloxy, d-C ⁇ -alkylthio,
  • W is O, S, NR d or NNR d R e ;
  • X 1 is O or NR f ;
  • X 2 is a single bond, -CO-, -CONH-, -COO-, -0-, -NR f -, -CH 2 -O-CO- or
  • R a , R b , R c , R d , R e , R f independently of one another are hydrogen, hydroxyl
  • R a , R b , R c are attached directly to an oxygen atom, they are not hydroxyl, Ci-C ⁇ -alkoxy or Cs-C ⁇ -cycloalkoxy;
  • Ra is independently defined like R a or is halogen or cyano; and X 11 is independently defined like X 1 ;
  • R 4 , R a , R b , R c , R d , R e , R f and/or Rs may be partially or fully halogenated and/or may carry 1 , 2 or 3 substituents R x , where
  • R x is cyano, SCN, nitro, hydroxyl, mercapto, oxo, C-i-C ⁇ -alkyl, C-i-C ⁇ -haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6- cycloalkyl, Cs-C ⁇ -halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6- cycloalkenyl, Ci-C ⁇ -alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyloxy, C3-C6- alkynyloxy, Ci-C6-alkylthio, C-i-C ⁇ -alkylcarbonyl, carboxyl, Ci-C ⁇ - alkoxycarbonyl, C-i-C ⁇ -al
  • R x may be unsubstituted or may carry 1 , 2 or 3 radicals R y , where
  • R y is cyano, nitro, halogen, hydroxyl, C-i-C ⁇ -alkyl, C-i-C ⁇ -haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6- cycloalkyl, Cs-C ⁇ -halocycloalkyl, Cs-C ⁇ -cycloalkenyl, C-i-C ⁇ - alkylsulfonyl, C-i-C ⁇ -alkylsulfinyl, Ci-C ⁇ -alkoxy, Ci-C ⁇ -haloalkoxy, C2-C6-alkenyloxy, Ci-C ⁇ -alkylthio, Ci-C ⁇ -alkoxycarbonyl, amino, Ci-C ⁇ -alkylamino, di-(Ci-C6-alkyl)amino, aminocarbonyl, Ci-
  • R ⁇ , R ⁇ independently of one another are hydrogen or Ci-C ⁇ -alkyl
  • R 5 is H, Ci-Cio-alkyl, C 2 -Cio-hydroxyalkyl, C 2 -Cio-alkenyl, C 2 -Cio-alkynyl, C 4 -Ci 0 - alkadienyl, C3-Cio-cycloalkyl, Ci-Cio-alkoxy, C2-Cio-alkenyloxy, C2-Cio-alkynyloxy, amino, d-Cs-alkylamino, di-(Ci-C8-alkyl)amino, phenyl, naphthyl or a saturated or unsaturated aromatic or non-aromatic 5- or 6-membered heterocycle which is attached via a carbon atom, where the heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members and may furthermore contain 1 or 2 CO groups as ring members;
  • R 5 may be partially or fully halogenated and/or may carry 1 , 2, 3 or 4 identical or different substituents R a1 ;
  • R 6 is independently defined like R 5 , or is a group #-CR 61 R 62 -(CR 63 R 64 ) q -(CR 65 R 66 )p-Y-Z in which
  • # is the point of attachment to the nitrogen atom
  • R 61 , R 62 , R 63 , R 64 , R 65 and R 66 independently of one another are hydrogen, Ci-Cs- alkyl, d-Cs-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, Cs-C ⁇ -cycloalkyl, Cs-C ⁇ -halocycloalkyl, C3-C6- cycloalkenyl, Cs-C ⁇ -halocycloalkenyl, phenyl, naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S; where
  • R 63 with R 61 or R 66 together with the atoms to which these radicals are attached may also form a five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated ring which, in addition to carbon atoms, may contain one, two or three heteroatoms from the group consisting of O, N and S as ring members and/or may carry one or more substituents R a1 ;
  • R 61 with R 62 , R 63 with R 64 , R 65 with R 66 in each case together may also be oxygen, thus forming carbonyl groups, and form a C 2 -Cs-alkylene, C 2 -Cs-alkenylene or C2-C5-alkynylene chain (which may be interrupted by one, two or three heteroatoms from the group consisting of O, N and S), thus forming spiro groups;
  • R 5 and R 61 together with atoms to which they are attached may form a 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated heterocycle which, in addition to carbon atoms, may contain one, two or three further heteroatoms from the group consisting of O, N and S as ring members;
  • R 61 to R 66 in each case independently of one another may be partially or fully halogenated and/or may carry one, two, three or four identical or different groups
  • each R a1 is independently cyano, nitro, hydroxyl, carboxyl, Ci-C ⁇ -alkyl, C 2 -C 8 - alkenyl, C2-C6-alkynyl, Cs-C ⁇ -cycloalkyl, C3-C 8 -cycloalkenyl, d-C ⁇ -alkoxy,
  • each R ⁇ is independently Ci-C 8 -alkyl, C3-C 8 -alkenyl, C3-C 8 -alkynyl, C3-C6- cycloalkyl or Cs-C ⁇ -cycloalkenyl;
  • aliphatic, alicyclic, aromatic or heterocyclic groups in the abovementioned groups R a1 and R ⁇ for their part may be partially or fully halogenated and/or may carry one, two or three groups R b1 ;
  • each R b1 is independently cyano, nitro, hydroxyl, mercapto, amino, carboxyl, C-i-Ce-alkyl, C 2 -C 8 -alkenyl, d-Ce-alkoxy, C 2 -C 8 -alkenyloxy, C 2 -C 8 - alkynyloxy, d-C ⁇ -alkylthio, Ci-C ⁇ -alkylamino, di-(Ci-C6-alkyl)amino, formyl, Ci-C ⁇ -alkylcarbonyl, Ci-C ⁇ -alkylsulfonyl, Ci-C ⁇ -alkylsulfinyl, Ci-C ⁇ - alkoxycarbonyl, Ci-C ⁇ -alkylcarbonyloxy, Ci-C ⁇ -alkoxycarbonyloxy, aminocarbonyl, aminothiocarbonyl, Ci-C ⁇ -alkylaminocarbonyl, di-(Ci-C6- alkyl
  • Y is oxygen or sulfur
  • Z is hydrogen, carboxyl, formyl, d-Cs-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, Cs-Ce-cycloalkyl, C 3 -C 8 -cycloalkenyl, C(O)R ⁇ , C(O)OR ⁇ , C(S)OR ⁇ ,
  • R A and R B independently of one another are hydrogen, C2-alkenyl, C2-alkynyl or one of the groups mentioned under R ⁇ ; or
  • R A and R B together with the nitrogen atom to which they are attached or R A and R ⁇ together with the carbon atoms and heteroatoms to which they are attached may also form a five- or six-membered saturated, partially unsaturated or aromatic ring which, in addition to carbon atoms, may contain one, two or three further heteroatoms from the group consisting of
  • N and S as ring members and/or may carry one or more substituents R a1 ;
  • Z with R 64 or R 66 may also form a five- or six-membered saturated or partially unsaturated ring which, in addition to carbon atoms and Y, may contain one or two further heteroatoms from the group consisting of O, N and S as ring members and/or may carry one or more substituents R a1 ;
  • group Z may be partially or fully halogenated and/or carry one, two or three groups R b1 ;
  • p 0, 1 , 2, 3, 4 or 5;
  • heterocycle may additionally contain 1 , 2 or 3 heteroatoms selected from the group consisting of O, S and N and/or 1 or 2 CO groups as ring members and where the heterocycle may carry 1 , 2 or 3 substituents selected from the group consisting of halogen, hydroxyl, cyano, nitro, carboxyl, Ci-Cs-alkyl, Ci-Cs-haloalkyl, C2-C8-hydroxyalkyl, Ci-Cs-alkoxy, Ci-Cs- haloalkoxy, d-Cs-alkylthio, d-Cs-haloalkylthio, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-Cs-alkyny
  • R 7 and R 8 together with the nitrogen atom to which they are attached form a saturated or unsaturated aromatic or non-aromatic 5- or 6-membered heterocyclic ring, where the heterocyclic ring may additionally contain 1 , 2 or 3 heteroatoms selected from the group consisting of O, S and N and/or 1 or 2 CO groups as ring members and where the heterocyclic ring may carry 1 , 2 or 3 substituents selected from the group consisting of halogen, hydroxyl, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
  • R 9 is hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, C3-Cio-cycloalkyl or C3-Cio-cycloalkenyl, where the five last-mentioned radicals may be partially or fully halogenated and/or may carry 1 , 2, 3 or 4 identical or different substituents selected from cyano, SCN, Ci-C4-alkyl, C3-Cio-cycloalkyl, C3-Cio-cycloalkenyl,
  • R 10 is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, Ci-Cio-alkylcarbonyl or C1-C10- alkoxycarbonyl;
  • Y 2 is d-Cs-alkylene, C2-Cs-alkenylene or C2-C8-alkynylene, where Y 2 may be interrupted by one, two, three or four heteroatoms from the group consisting of NR h , O and S(O) r ; r is O, 1 or 2;
  • T 3 is R h , R z , OR h , SR h or NR h R'; V 1 is O or S; b is O or i ; c is 0, 1 , 2, 3, 4 or 5; R z is NR 5 R 6 or Ci-Cio-alkyl, Ci-Cio-haloalkyl, C 2 -Cio-alkenyl, C 2 -Cio-halo- alkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Ci2-cycloalkenyl, C3- Ci2-halocycloalkenyl, phenyl, halophenyl, naphthyl, halonaphthyl or a 5-, 6-, 7-, 8-, 9-, or 10-membered saturated, partially unsaturated or aromatic heterocyclic ring which is attached via carbon, which may be partially or fully halogenated and contains 1
  • RJ, R k , R 1 , R m , R n , R 0 , RP, R ⁇ , R r are each independently H, d-C 8 -alkyl, CrC 8 - haloalkyl, C2-C8-hydroxyalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8- alkynyl, Cs-Cs-cycloalkyl or Cs-Cs-cycloalkenyl; or
  • R m and R n , R 0 and RP and/or R? and R r together with the nitrogen atom to which they are attached form a four-, five- or six-membered saturated or partially unsaturated ring which may carry one, two, three or four substituents independently of one another selected from L 5 ;
  • a 1 is hydrogen, hydroxyl, d-Cs-alkyl, amino, d-Cs-alkylamino or di-(Ci-C8- alkyl)amino;
  • a 2 is C2-C8-alkenyl, d-Cs-alkoxy, Ci-C ⁇ -haloalkoxy, C2-Cio-alkenyloxy, C2-C10- alkynyloxy or one of the groups mentioned under A 1 ;
  • n O, 1 or 2;
  • each L 3 is independently halogen, hydroxyl, mercapto (SH), cyano, cyanato (OCN), nitro, carboxyl (COOH), Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-hydroxyalkyl, Ci-Cio-alkoxy, Ci-Cio-haloalkoxy, Ci-Cio-alkylthio, C2-Cio-alkenyl, C2-C10- haloalkenyl, C2-Cio-alkenyloxy, C2-Cio-alkynyl, C3-Cio-cycloalkyl, C3-C10- cycloalkoxy, C3-Cio-cycloalkenyl, C1-C10- alkoxycarbonyl, Ci-Cio-haloalkoxycarbonyl, C2-Cio-alkenyloxycarbonyl, C1-C10- alkylcarbonyloxy,
  • heterocyclic ring contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members and may furthermore contain one or two CO groups as ring members, where the aliphatic, alicyclic, aromatic and heterocyclic groups in L 3 for their part may be partially or fully halogenated and/or may carry 1 , 2 or 3 substituents L 4 ;
  • each L 4 is independently cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Ci-C ⁇ -alkyl, d-C ⁇ -haloalkyl, C2-C8-alkenyl, C 2 -C 8 -haloalkenyl, C 2 -C 8 -alkynyl, C 2 -C 8 -haloalkynyl, C 4 -C 8 -alkadienyl, C 2 -C 8 - alkenyloxy, C 2 -C 8 -alkynyloxy, d-C ⁇ -alkoxy, d-C ⁇ -haloalkoxy, d-C ⁇ -alkylthio, Ci-C ⁇ -alkylamino, di-(Ci-C6-alkyl)amino, C3-C 8 -cycloalkylamino, (Ci-C6-alkyl)(C3- C 8
  • each L 5 is in each case independently selected from the group consisting of hydroxyl, cyano, nitro, Ci-C 8 -alkyl, Ci-C 8 -haloalkyl, C 2 -C 8 -hydroxyalkyl, Ci-C 8 -alkoxy, Ci-C 8 -haloalkoxy, Ci-C 8 -alkylthio, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 2 -C 8 - alkenyloxy, C 2 -C 8 -alkynyl, C 2 -C 8 -alkynyloxy, C3-C 8 -cycloalkyl, amino, Ci-C 8 - alkylamino and di-(Ci-C 8 -alkyl)amino.
  • the present invention also provides the use of pyrazine compounds of the formula I, their N-oxides and/or their agriculturally useful salts for controlling harmful fungi. Moreover, the invention provides the use of the pyrazine compounds I, their N-oxides and/or their pharmaceutically acceptable salts for preparing a medicament for the treatment of cancer.
  • the invention further provides fungicidal or pharmaceutical compositions comprising these compounds I, their N-oxides and/or their agriculturally or pharmaceutically acceptable salts and suitable carriers. Suitable agriculturally and/or pharmaceutically acceptable carriers are described below.
  • the compounds I can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the compounds of the invention may be present as a mixture of stereoisomers, e.g. a racemate, individual stereoisomers, or as an optically active form.
  • 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 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, preferably
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate 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.
  • Suitable pharmaceutically acceptable salts are especially physiologically tolerated salts of the compound I, in particular the acid addition salts with physiologically acceptable acids.
  • suitable organic and inorganic acids are hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, Ci-C4-alkylsulfonic acids, such as methanesulfonic acid, aromatic sulfonic acids, such as benzenesulfonic acid and toluenesulfonic acid, oxalic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, adipic acid and benzoic acid.
  • suitable acids are described, for example, in Fort suitse der Arzneistoffforschung, Volume 10, pages 224 ff., Birkhauser Verlag, Basle and Stuttgart, 1966, the entire contents of which is expressly incorporated herein by way of reference.
  • C n -Cm indicates the number of carbon atoms possible in each case in the substituent or substitutent moiety in question:
  • Halogen fluorine, chlorine, bromine and iodine
  • Ci-C2-Alkyl is methyl or ethyl.
  • CrC 4 -AIkVl is additionally also, for example, propyl, isopropyl, butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1 ,1-dimethylethyl (tert-butyl).
  • Ci-C ⁇ -Alkyl is additionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl,
  • d-Cs-Alkyl is additionally also, for example, heptyl, octyl, 2-ethylhexyl and positional isomers thereof.
  • Ci-Cio-Alkyl is additionally also, for example, nonyl, decyl and positional isomers thereof.
  • Branched Cs-Cs-alkyl is an alkyl group having 3 to 8 carbon atoms, at least one of which is a secondary or tertiary carbon atom. Examples are isopropyl, tert-butyl, 2-butyl, isobutyl (2-methylpropyl), 2-pentyl, 2-methylbutyl, 2-hexyl, 3-methylpentyl, 1 ,1- dimethylbutyl, 1 ,2-dimethylbutyl, 1-methyl-1-ethylpropyl and the like.
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 1 to 4, 1 to 6, 1 to 8 or 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above: in particular Ci-C2-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,
  • Ci-Cio-Hydroxyalkyl straight-chain or branched alkyl groups having 1 to 2, 1 to 4, 2 to 4, 1 to 6, 2 to 6, 1 to 8, 2 to 8, 1 to 10 or 2 to 10 carbon atoms (as mentioned above), where at least one of the hydrogen atoms is replaced by a hydroxyl group, such as in 2-hydroxyethyl or 3-hydroxypropyl.
  • Alkadienyl doubly unsaturated straight-chain or branched hydrocarbon radicals having 4 to 6, 4 to 8 or 4 to 10 carbon atoms and two double bonds in any position, but preferably not cumulated, for example 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
  • Haloalkenyl and the haloalkenyl moieties in haloalkenyloxy, haloalkenylcarbonyl and the like unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and a double bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like;
  • Haloalkynyl and the haloalkynyl moieties in haloalkynyloxy, haloalkynylcarbonyl and the like unsaturated straight-chain or branched hydrocarbon radicals having 3 to 4, 3 to 6, 3 to 8 or 3 to 10 carbon atoms and one or two triple bonds in any position (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;
  • Halocycloalkyl and the halocycloalkyl moieties in halocycloalkoxy, halocycloalkylcarbonyl and the like monocyclic saturated hydrocarbon groups having 3 to 6, 3 to 8 or 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; Ci-C4-alkyl (as defined above) where one hydrogen atom is replaced by a cycloalkyl group, for example cyclopropyl methyl, cyclopentylmethyl, cyclohexylmethyl and the like.
  • Cycloalkenyl monocyclic monounsaturated hydrocarbon groups having 3 to 10, 3 to 8, 3 to 6, preferably 5 to 6, carbon ring members, such as cyclopenten-1-yl, cyclopenten- 3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl and the like;
  • Halocycloalkenyl monocyclic monounsaturated hydrocarbon groups having 3 to 10, 3 to 8, 3 to 6, preferably 5 to 6, 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;
  • bicycloalkyl a bicyclic hydrocarbon radical having 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, bicyclo[4.4.0]decyl, decalin and the like;
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • C1-C4- Alkoxy is additionally, for example, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1-dimethylethoxy (tert- butoxy).
  • Ci-C ⁇ -Alkoxy is additionally, for example, 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 or 1-ethyl-2-methylpropoxy.
  • Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.
  • Ci-Cio-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.
  • Ci-C2-Haloalkoxy an alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
  • Ci-C2-Haloalkoxy is, 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-chloro-2- fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC 2 Fs Ci-C4-Haloalkoxy
  • Ci-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
  • Alkenyloxy alkenyl as mentioned above which is attached via an oxygen atom, for example Cs-C ⁇ -alkenyloxy, such as 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy, 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,
  • Haloalkenyloxy an alkenyloxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
  • Alkynyloxy alkynyl as mentioned above which is attached via an oxygen atom, for example Cs-C ⁇ -alkynyloxy, such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy,
  • Haloalkynyloxy an alkynyloxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
  • Cycloalkoxy cycloalkoxy as mentioned above which is attached via an oxygen atom, for example C3-Cio-cycloalkoxy or Cs-Cs-cycloalkoxy, such as cyclopropoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy and the like;
  • Cycloalkenyloxy cycloalkenyloxy as mentioned above which is attached via an oxygen atom, for example C3-Cio-cycloalkenyloxy, Cs-Cs-cycloalkenyloxy or, preferably, Cs-C ⁇ - cycloalkenyloxy, such as cyclopent-1-enoxy, cyclopent-2-enoxy, cyclohex-1-enoxy and cyclohex-2-enoxy;
  • Alkoxyalkyl alkyl as defined above having 1 to 8, 1 to 6 or 1 to 4, in particular 1 to 3, carbon atoms, in which one hydrogen atom is replaced by an alkoxy group having 1 to 8, 1 to 6 or 1 to 4 carbon atoms, for example methoxymethyl, 2-methoxyethyl, ethoxymethyl, 3-methoxypropyl, 3-ethoxypropyl and the like.
  • Cyanoalkyl alkyl as defined above having 1 to 8, 1 to 6 or 1 to 4, in particular 1 to 3, carbon atoms in which one hydrogen atom is replaced by a cyano group;
  • Alkylcarbonyl group of the formula R-CO- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-C 8 -alkyl, d-Ce-alkyl, Ci-C 4 -alkyl or Ci-C 2 -alkyl. Examples are acetyl, propionyl and the like.
  • Alkylthiocarbonyl group of the formula R-CS- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs-alkyl, C-i-C ⁇ -alkyl, Ci-C4-alkyl or Ci-C2-alkyl. Examples are thioacetyl, thiopropionyl and the like.
  • Haloalkylcarbonyl group of the formula R-CO- in which R is a haloalkyl group as defined above, for example Ci-Cio-haloalkyl, Ci-Cs-haloalkyl, C-i-C ⁇ -haloalkyl, C1-C4- haloalkyl or Ci-C2-haloalkyl. Examples are trifluoroacetyl, trifluoropropionyl and the like.
  • Haloalkylthiocarbonyl group of the formula R-CS- in which R is a haloalkyl group as defined above, for example Ci-Cio-haloalkyl, Ci-Cs-haloalkyl, d-C ⁇ -haloalkyl, C1-C4- haloalkyl or Ci-C2-haloalkyl. Examples are trifluorothioacetyl, trifluorothiopropionyl and the like.
  • Alkenylcarbonyl group of the formula R-CO- in which R is an alkenyl group as defined above, for example C2-Cio-alkenyl, C2-Cs-alkenyl, C2-C6-alkenyl or C2-C4-alkenyl.
  • Alkenylthiocarbonyl group of the formula R-CS- in which R is an alkenyl group as defined above, for example C2-Cio-alkenyl, C2-Cs-alkenyl, C2-C6-alkenyl or C2-C4- alkenyl.
  • Haloalkenylcarbonyl group of the formula R-CO- in which R is a haloalkenyl group as defined above, for example C2-Cio-haloalkenyl, C2-C8-haloalkenyl, C2-C6-haloalkenyl or C2-C4-haloalkenyl.
  • Haloalkenylthiocarbonyl group of the formula R-CS- in which R is a haloalkenyl group as defined above, for example C2-Cio-haloalkenyl, C2-C8-haloalkenyl, C2-C6-haloalkenyl or C2-C4-haloalkenyl.
  • Alkynylcarbonyl group of the formula R-CO- in which R is an alkynyl group as defined above, for example C2-Cio-alkynyl, C2-C8-alkynyl, C2-C6-alkynyl or C2-C4-alkynyl.
  • Alkynylthiocarbonyl group of the formula R-CS- in which R is an alkynyl group as defined above, for example C2-Cio-alkynyl, C2-C8-alkynyl, C2-C6-alkynyl or C2-C4- alkynyl.
  • Haloalkynylcarbonyl group of the formula R-CO- in which R is a haloalkynyl group as defined above, for example C2-Cio-haloalkynyl, C2-Cs-haloalkynyl, C2-C6-haloalkynyl or C2-C4-haloalkynyl.
  • Haloalkynylthiocarbonyl group of the formula R-CS- in which R is a haloalkynyl group as defined above, for example C2-Cio-haloalkynyl, C2-C8-haloalkynyl, C2-C6-haloalkynyl or C2-C4-haloalkynyl.
  • Cycloalkylcarbonyl group of the formula R-CO- in which R is a cycloalkyl group as defined above, for example C3-Cio-cycloalkyl, Cs-Cs-cycloalkyl, Cs-C ⁇ -cycloalkyl or C5-C6-cycloalkyl.
  • Cycloalkylthiocarbonyl group of the formula R-CS- in which R is a cycloalkyl group as defined above, for example C3-Cio-cycloalkyl, Cs-Cs-cycloalkyl, Cs-C ⁇ -cycloalkyl or Cs-Ce-cycloalkyl.
  • Cycloalkenylcarbonyl group of the formula R-CO- in which R is a cycloalkenyl group as defined above, for example C3-Cio-cycloalkenyl, Cs-Cs-cycloalkenyl, Cs-C ⁇ -cycloalkenyl or C5-C6-cycloalkenyl.
  • Cycloalkenylthiocarbonyl group of the formula R-CS- in which R is a cycloalkenyl group as defined above, for example C3-Cio-cycloalkenyl, Cs-Cs-cycloalkenyl, C3-C6- cycloalkenyl or Cs-C ⁇ -cycloalkenyl.
  • Alkylcarbonyloxy group of the formula R-CO-O- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, C-i-Cs-alkyl, Ci-C ⁇ -alkyl, Ci-C4-alkyl or Ci-C2-alkyl. Examples are acetyloxy, propionyloxy and the like.
  • Alkylthiocarbonyloxy group of the formula R-CS-O- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, C-i-Cs-alkyl, Ci-C ⁇ -alkyl, Ci-C4-alkyl or C1-C2- alkyl. Examples are thioacetyloxy, thiopropionyloxy and the like.
  • Haloalkylcarbonyloxy group of the formula R-CO-O- in which R is a haloalkyl group as defined above, for example Ci-Cio-haloalkyl, Ci-Cs-haloalkyl, C-i-C ⁇ -haloalkyl, C1-C4- haloalkyl or Ci-C2-haloalkyl. Examples are trifluoracetyloxy, trifluropropionyloxy and the like.
  • Haloalkylthiocarbonyloxy group of the formula R-CS-O- in which R is a haloalkyl group as defined above, for example Ci-Cio-haloalkyl, Ci-Cs-haloalkyl, C-i-C ⁇ -haloalkyl, C1-C4- haloalkyl or Ci-C2-haloalkyl. Examples are trifluorothioacetyloxy, trifluorothiopropionyloxy and the like.
  • Alkenylcarbonyloxy group of the formula R-CO-O- in which R is an alkenyl group as defined above, for example C2-Cio-alkenyl, C2-C8-alkenyl, C2-C6-alkenyl or C2-C4- alkenyl.
  • Alkenylthiocarbonyloxy group of the formula R-CS-O- in which R is an alkenyl group as defined above, for example C2-Cio-alkenyl, C2-C8-alkenyl, C2-C6-alkenyl or C2-C4- alkenyl.
  • Haloalkenylcarbonyloxy group of the formula R-CO-O- in which R is a haloalkenyl group as defined above, for example C2-Cio-haloalkenyl, C2-C8-haloalkenyl, C2-C6- haloalkenyl or C2-C4-haloalkenyl.
  • Haloalkenylthiocarbonyloxy group of the formula R-CS-O- in which R is a haloalkenyl group as defined above, for example C2-Cio-haloalkenyl, C2-C8-haloalkenyl, C2-C6- haloalkenyl or C2-C4-haloalkenyl.
  • Alkynylcarbonyloxy group of the formula R-CO-O- in which R is an alkynyl group as defined above, for example C2-Cio-alkynyl, C2-Cs-alkynyl, C2-C6-alkynyl or C2-C4- alkynyl.
  • Alkynylthiocarbonyloxy group of the formula R-CS-O- in which R is an alkynyl group as defined above, for example C2-Cio-alkynyl, C2-C8-alkynyl, C2-C6-alkynyl or C2-C4- alkynyl.
  • Haloalkynylcarbonyloxy group of the formula R-CO-O- in which R is a haloalkynyl group as defined above, for example C2-Cio-haloalkynyl, C2-Cs-haloalkynyl, C2-C6- haloalkynyl or C2-C4-haloalkynyl.
  • Haloalkynylthiocarbonyloxy group of the formula R-CS-O- in which R is a haloalkynyl group as defined above, for example C2-Cio-haloalkynyl, C2-C8-haloalkynyl, C2-C6- haloalkynyl or C2-C4-haloalkynyl.
  • Cycloalkylcarbonyloxy group of the formula R-CO-O- in which R is a cycloalkyl group as defined above, for example C3-Cio-cycloalkyl, Cs-Cs-cycloalkyl, Cs-C ⁇ -cycloalkyl or C5-C6-cycloalkyl.
  • Cycloalkylthiocarbonyloxy group of the formula R-CS-O- in which R is a cycloalkyl group as defined above, for example C3-Cio-cycloalkyl, Cs-Cs-cycloalkyl, C3-C6- cycloalkyl or Cs-C ⁇ -cycloalkyl.
  • Cycloalkenylcarbonyloxy group of the formula R-CO-O- in which R is a cycloalkenyl group as defined above, for example C3-Cio-cycloalkenyl, Cs-Cs-cycloalkenyl, C3-C6- cycloalkenyl or Cs-C ⁇ -cycloalkenyl.
  • Cycloalkenylthiocarbonyloxy group of the formula R-CS-O- in which R is a cycloalkenyl group as defined above, for example C3-Cio-cycloalkenyl, Cs-Cs-cycloalkenyl, C3-C6- cycloalkenyl or Cs-C ⁇ -cycloalkenyl.
  • Alkoxycarbonyl group of the formula R-CO- in which R is an alkoxy group as defined above, for example Ci-Cio-alkoxy, Ci-Cs-alkoxy, Ci-C6-alkoxy, Ci-C4-alkoxy or C1-C2- alkoxy. Examples are methoxycarbonyl, ethoxycarbonyl and the like.
  • Alkoxythiocarbonyl group of the formula R-CS- in which R is an alkoxy group as defined above, for example Ci-Cio-alkoxy, Ci-Cs-alkoxy, Ci-C6-alkoxy, Ci-C4-alkoxy or Ci-C2-alkoxy. Examples are methoxythiocarbonyl, ethoxythiocarbonyl and the like.
  • Haloalkoxycarbonyl group of the formula R-CO- in which R is a haloalkoxy group as defined above, for example Ci-Cio-haloalkoxy, Ci-Cs-haloalkoxy, Ci-C6-haloalkoxy, Ci-C4-haloalkoxy or Ci-C2-haloalkoxy. Examples are trifluoromethoxycarbonyl, trifluoroethoxycarbonyl and the like.
  • Haloalkoxythiocarbonyl group of the formula R-CS- in which R is a haloalkoxy group as defined above, for example Ci-Cio-haloalkoxy, Ci-Cs-haloalkoxy, Ci-C6-haloalkoxy, Ci-C4-haloalkoxy or Ci-C2-haloalkoxy. Examples are trifluoromethoxythiocarbonyl, trifluoroethoxythiocarbonyl and the like.
  • Alkenyloxycarbonyl group of the formula R-CO- in which R is an alkenyloxy group as defined above, for example C2-Cio-alkenyloxy, C2-Cs-alkenyloxy, C2-C6-alkenyloxy or C2-C4-alkenyloxy.
  • Alkenyloxythiocarbonyl group of the formula R-CS- in which R is an alkenyloxy group as defined above, for example C2-Cio-alkenyloxy, C2-C8-alkenyloxy, C2-C6-alkenyloxy or C2-C4-alkenyloxy.
  • Haloalkenyloxycarbonyl group of the formula R-CO- in which R is a haloalkenyloxy group as defined above, for example C2-Cio-haloalkenyloxy, C2-C8-haloalkenyloxy, C2-C6-haloalkenyloxy or C2-C4-haloalkenyloxy.
  • Haloalkenyloxythiocarbonyl group of the formula R-CS- in which R is a haloalkenyloxy group as defined above, for example C2-Cio-haloalkenyloxy, C2-C8-haloalkenyloxy, C2-C6-haloalkenyloxy or C2-C4-haloalkenyloxy.
  • Alkynyloxycarbonyl group of the formula R-CO- in which R is an alkynyloxy group as defined above, for example C2-Cio-alkynyloxy, C2-C8-alkynyloxy, C2-C6-alkynyloxy or C2-C4-alkynyloxy.
  • Alkynyloxythiocarbonyl group of the formula R-CS- in which R is an alkynyloxy group as defined above, for example C2-Cio-alkynyloxy, C2-Cs-alkynyloxy, C2-C6-alkynyloxy or C 2 -C 4 -alkynyloxy.
  • Haloalkynyloxycarbonyl group of the formula R-CO- in which R is a haloalkynyloxy group as defined above, for example C2-Cio-haloalkynyloxy, C2-C8-haloalkynyloxy, C2-C6-haloalkynyl or C2-C4-haloalkynyloxy.
  • Haloalkynyloxythiocarbonyl group of the formula R-CS- in which R is a haloalkynyloxy group as defined above, for example C2-Cio-haloalkynyloxy, C2-C8-haloalkynyloxy, C2-C6-haloalkynyl or C2-C4-haloalkynyloxy.
  • Cycloalkyloxycarbonyl group of the formula R-CO- in which R is a cycloalkyloxy group as defined above, for example C3-Cio-cycloalkyloxy, Cs-Cs-cycloalkyloxy, C3-C6- cycloalkyloxy or Cs-C ⁇ -cycloalkyloxy.
  • Cycloalkyloxythiocarbonyl group of the formula R-CS- in which R is a cycloalkyloxy group as defined above, for example C3-Cio-cycloalkyloxy, Cs-Cs-cycloalkyloxy, C3-C6- cycloalkyloxy or Cs-C ⁇ -cycloalkyloxy.
  • Cycloalkenyloxycarbonyl group of the formula R-CO- in which R is a cycloalkenyloxy group as defined above, for example C3-Cio-cycloalkenyloxy, Cs-Cs-cycloalkenyloxy, C3-C6-cycloalkenyloxy or Cs-C ⁇ -cycloalkenyloxy.
  • Cycloalkenyloxythiocarbonyl group of the formula R-CS- in which R is a cycloalkenyloxy group as defined above, for example C3-Cio-cycloalkenyloxy, C3-C8- cycloalkenyloxy, Cs-C ⁇ -cycloalkenyloxy or Cs-C ⁇ -cycloalkenyloxy.
  • Alkoxycarbonyloxy group of the formula R-CO-O- in which R is an alkoxy group as defined above, for example Ci-Cio-alkoxy, Ci-Cs-alkoxy, Ci-C ⁇ -alkoxy, Ci-C4-alkoxy or Ci-C2-alkoxy. Examples are methoxycarbonyl, ethoxycarbonyl and the like.
  • Alkoxythiocarbonyloxy group of the formula R-CS-O- in which R is an alkoxy group as defined above, for example Ci-Cio-alkoxy, Ci-Cs-alkoxy, Ci-C ⁇ -alkoxy, Ci-C4-alkoxy or Ci-C2-alkoxy. Examples are methoxycarbonyl, ethoxycarbonyl and the like.
  • Haloalkoxycarbonyloxy group of the formula R-CO-O- in which R is a haloalkoxy group as defined above, for example Ci-Cio-haloalkoxy, Ci-Cs-haloalkoxy, Ci-C6-haloalkoxy, Ci-C4-haloalkoxy or Ci-C2-haloalkoxy. Examples are trifluoromethoxycarbonyl, trifluoroethoxycarbonyl and the like.
  • Haloalkoxythiocarbonyloxy group of the formula R-CS-O- in which R is a haloalkoxy group as defined above, for example Ci-Cio-haloalkoxy, Ci-Cs-haloalkoxy, C-i-C ⁇ - haloalkoxy, Ci-C4-haloalkoxy or Ci-C2-haloalkoxy. Examples are trifluoromethoxycarbonyl, trifluoroethoxycarbonyl and the like.
  • Alkenyloxycarbonyloxy group of the formula R-CO-O- in which R is an alkenyloxy group as defined above, for example C2-Cio-alkenyloxy, C2-C8-alkenyloxy, C2-C6- alkenyloxy or C2-C4-alkenyloxy.
  • Alkenyloxythiocarbonyloxy group of the formula R-CS-O- in which R is an alkenyloxy group as defined above, for example C2-Cio-alkenyloxy, C2-C8-alkenyloxy, C2-C6- alkenyloxy or C2-C4-alkenyloxy.
  • Haloalkenyloxycarbonyloxy group of the formula R-CO-O- in which R is a haloalkenyloxy group as defined above, for example C2-Cio-haloalkenyloxy, C2-C8- haloalkenyloxy, C2-C6-haloalkenyloxy or C2-C4-haloalkenyloxy.
  • Haloalkenyloxythiocarbonyloxy group of the formula R-CS-O- in which R is a haloalkenyloxy group as defined above, for example C2-Cio-haloalkenyloxy, C2-C8- haloalkenyloxy, C2-C6-haloalkenyloxy or C2-C4-haloalkenyloxy.
  • Alkynyloxycarbonyloxy group of the formula R-CO-O- in which R is an alkynyloxy group as defined above, for example C2-Cio-alkynyloxy, C2-Cs-alkynyloxy, C2-C6- alkynyloxy or C2-C4-alkynyloxy.
  • Alkynyloxythiocarbonyloxy group of the formula R-CS-O- in which R is an alkynyloxy group as defined above, for example C2-Cio-alkynyloxy, C2-C8-alkynyloxy, C2-C6- alkynyloxy or C2-C4-alkynyloxy.
  • Haloalkynyloxycarbonyloxy group of the formula R-CO-O- in which R is a haloalkynyloxy group as defined above, for example C2-Cio-haloalkynyloxy, C2-C8- haloalkynyloxy, C2-C6-haloalkynyl or C2-C4-haloalkynyloxy.
  • Haloalkynyloxythiocarbonyloxy group of the formula R-CS-O- in which R is a haloalkynyloxy group as defined above, for example C2-Cio-haloalkynyloxy, C2-C8- haloalkynyloxy, C2-C6-haloalkynyl or C2-C4-haloalkynyloxy.
  • Cycloalkyloxycarbonyloxy group of the formula R-CO-O- in which R is a cycloalkyloxy group as defined above, for example C3-Cio-cycloalkyloxy, Cs-Cs-cycloalkyloxy, C3-C6- cycloalkyloxy or Cs-C ⁇ -cycloalkyloxy.
  • Cycloalkyloxythiocarbonyloxy group of the formula R-CS-O- in which R is a cycloalkyloxy group as defined above, for example C3-Cio-cycloalkyloxy, Cs-Cs- cycloalkyloxy, C3-C6-cycloalkyloxy or Cs-C ⁇ -cycloalkyloxy.
  • Cycloalkenyloxycarbonyloxy group of the formula R-CO-O- in which R is a cycloalkenyloxy group as defined above, for example C3-Cio-cycloalkenyloxy, C3-C8- cycloalkenyloxy, Cs-C ⁇ -cycloalkenyloxy or Cs-C ⁇ -cycloalkenyloxy.
  • Cycloalkenyloxythiocarbonyloxy group of the formula R-CS-O- in which R is a cycloalkenyloxy group as defined above, for example C3-Cio-cycloalkenyloxy, C3-C8- cycloalkenyloxy, Cs-C ⁇ -cycloalkenyloxy or Cs-C ⁇ -cycloalkenyloxy.
  • Alkylamino group of the formula RHN- in which R is an alkyl group as defined above.
  • Dialkylamino group of the formula RRN- in which each R independently is an alkyl group as defined above.
  • Alkylaminocarbonyl group of the formula RHN-CO- in which R is an alkyl group as defined above.
  • Dialkylaminocarbonyl group of the formula RRN-CO- in which each R independently is an alkyl group as defined above.
  • Alkylaminothiocarbonyl group of the formula RHN-CS- in which R is an alkyl group as defined above.
  • Dialkylaminothiocarbonyl group of the formula RRN-CS- in which each R independently is an alkyl group as defined above.
  • Alkylaminocarbonyloxy group of the formula RHN-CO-O- in which R is an alkyl group as defined above.
  • Dialkylaminocarbonyloxy group of the formula RRN-CO-O- in which each R independently is an alkyl group as defined above.
  • Alkylaminothiocarbonyloxy group of the formula RHN-CS-O- in which R is an alkyl group as defined above.
  • Dialkylaminothiocarbonyloxy group of the formula RRN-CS-O- in which each R independently is an alkyl group as defined above.
  • Alkylthio alkyl as defined above which is attached via a sulfur atom.
  • Haloalkylthio haloalkyl as defined above which is attached via a sulfur atom.
  • Alkylsulfinyl (sometimes also referred to as alkylsulfoxyl): alkyl as defined above which is attached via an SO group.
  • Alkylsulfonyl alkyl as defined above which is attached via an S(0)2 group.
  • Aryl carbocyclic aromatic radical having 6 to 14 carbon atoms, such as phenyl, naphthyl, anthracenyl or phenanthrenyl.
  • C ⁇ -Cio-Aryl is phenyl or naphthyl.
  • Aryloxy carbocyclic aromatic radical having 6 to 14 carbon atoms which is attached via oxygen, such as phenoxy, naphthyloxy, anthracenyloxy or phenanthrenyloxy.
  • C ⁇ -Cio- Aryloxy is phenoxy or naphthoxy.
  • Arylthio carbocyclic aromatic radical having 6 to 14 carbon atoms which is attached via sulfur, such as phenylthio, naphthylthio, anthracenylthio or phenanthrenylthio.
  • C ⁇ -Cio- Arylthio is phenylthio or naphthylthio.
  • Arylalkyl alkyl (as defined above), for example d-Cs-alkyl, Ci-C ⁇ -alkyl or Ci-C4-alkyl, where a hydrogen atom is replaced by an aryl group, such as benzyl, phenethyl and the like.
  • Arylalkoxy alkoxy (as defined above), for example Ci-Cs-alkoxy, Ci-C ⁇ -alkoxy or Ci- C4-alkoxy, where one hydrogen atom is replaced by an aryl group, such as benzyloxy, phenethyloxy and the like.
  • a seven-membered saturated or partially unsaturated heterocycle which contains one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur as ring members: for example mono- and bicyclic heterocycles having
  • ring members which, in addition to carbon ring members, contain one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, for example tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro[1 H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -A-, -5-, -6- or -7-yl,
  • tetra- and hexahydroazepinyl such as 2,3,4,5-tetrahydro[1 H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -A-, -5-, -6
  • a five- or six-membered aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur, for example 5-membered heteroaryl which is attached via carbon and contains one to three nitrogen atoms or one or two nitrogen atoms and one 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-
  • alkylene divalent branched or preferably unbranched chains having 1 to 8 carbon atoms, for example CH 2 , CH 2 CH 2 , -CH(CH 3 )-, CH 2 CH 2 CH 2 , CH(CH 3 )CH 2 , CH 2 CH(CH 3 ), CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 und CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 .
  • oxyalkylene divalent unbranched chains of 2 to 4 CH 2 groups where one valency is attached to the skeleton via an oxygen atom, for example OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 CH 2 CH 2 CH 2 ;
  • oxyalkyleneoxy divalent unbranched chains of 1 to 3 CH 2 groups where both valencies are attached to the skeleton via an oxygen atom, for example OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O.
  • R 1 ' is Ci-Cio-alkyl, Cs-Cs-alkenyl, Cs-Cs-alkynyl, Cs-C ⁇ -cycloalkyl, C5-C6-cycloalkenyl, where the two last-mentioned groups may carry a Ci-C4-alkylidene group, or is phenyl or a 5- or 6-membered saturated or aromatic heterocycle which is attached via carbon.
  • R 1 ' may be partially or fully halogenated or carry one, two, three or four identical or different groups L 3 , which are as defined above.
  • L 3 is preferably selected from the group consisting of halogen, cyano, nitro hydroxyl, Ci-C ⁇ -alkyl, C-i-C ⁇ -haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C ⁇ -alkoxy, C-i-Ce-alkylthio, d-Ce-alkylsulfinyl, d-Ce-alkylsulfonyl, d-Ce-alkylcarbonyl, Ci-C 6 - alkoxycarbonyl, Ci-C ⁇ -alkoximino, C2-C6-alkenyloximino, trimethylsilyl, C2-C6- alkynyloximino, Cs-C ⁇ -cycloalkyl, Cs-C ⁇ -cycloalkenyl, phenyl, and
  • L 4 is preferably selected from the group consisting of halogen, cyano, Ci-C ⁇ -alkyl, C-i-C ⁇ -haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C-i-C ⁇ - alkylcarbonyl, Ci-C ⁇ -haloalkylcarbonyl and C-i-C ⁇ -alkoxy.
  • R 1 ' is Ci-Cio-alkyl, Cs-Cs-alkenyl, Cs-Cs-alkynyl, C3-C6- cycloalkyl, Cs-C ⁇ -cycloalkenyl, phenyl, a 5- or 6-membered saturated or aromatic heterocycle, phenyl bound via CH2 or a 5- or 6-membered saturated or aromatic heterocycle bound via CH2, here R 1 ' may be partially or fully halogenated or carry one, two, three or four identical or different groups L 3 , which are as defined above.
  • R 1 ' is Ci-Cs-alkyl, especially branched Cs-Cs-alkyl, Ci-C ⁇ - haloalkyl, Cs-Cs-alkenyl, especially branched Cs-Cs-alkenyl, Cs-C ⁇ -cycloalkyl, which may carry a Ci-C4-alkyl group, or Cs-C ⁇ -cycloalkenyl, which may carry a Ci-C4-alkyl group.
  • R 1 is branched Cs-Cs-alkyl, such as isopropyl, sec-butyl, isobutyl (2-methylpropyl), tert-butyl, 2- and 3-pentyl, 2- and 3-methylbutyl, 1 ,1- dimethylpropyl, 2,2-dimethylpropyl, 2-and 3-hexyl, 2-, 3- and 4-methylpentyl and the like.
  • the branch point is preferably not at the carbon atom through which the radical R 1 ' is attached to the pyrazine ring.
  • alkyl radicals are isobutyl, 2- and 3- methylbutyl, 2,2-dimethylpropyl, 2-, 3- and 4-methylpentyl and the like.
  • R 1 ' is isobutyl (2-methylpropyl) or 2-methylbutyl.
  • R 1 is preferably a group NR 5 R 6 .
  • R 5 is preferably d-Cs-alkyl, d-Cs-haloalkyl, Ci-Cs-hydroxyalkyl, Ci-d-alkoxy- Ci-C4-alkyl, Ci-Cs-alkyl which carries a substituent selected from the group consisting of COOH, Ci-C4-alkoxycarbonyl, aminocarbonyl, d-Cs-alkylaminocarbonyl, di-(Ci-Cs- alkyl)aminocarbonyl and Ci-d-alkylcarbonyloxy, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci- d-alkyl or phenyl which optionally carries 1 , 2 or 3 substituents selected from the group consisting of halogen, d-d-alkoxy and d-d-alkyl.
  • R 5 is straight-chain or branched Ci-Cs-alkyl or straight-chain or branched Ci-Cs-haloalkyl, straight-chain or branched Cs-Cs-alkyl and straight-chain or branched C2-Cs-haloalkyl being more preferred. Even more preferably, R 5 is branched Cs-C ⁇ -alkyl, straight-chain C2-C6-haloalkyl or branched Cs-C ⁇ -haloalkyl.
  • branched Cs-C ⁇ -alkyl is, for example, isopropyl, sec-butyl, isobutyl, tert-butyl, 1-methylpropyl, 2- and 3-pentyl, 2- and 3-methylbutyl, 1 ,1-dimethylpropyl, 2,2-dimethylpropyl, 1 ,2-dimethylpropyl, 2- and 3-hexyl, 2-, 3- and 4-methylpentyl, 1 ,2,2-trimethylpropyl and the like.
  • the branched Cs-C ⁇ -alkyl radical has a branching point at the 1 -position of the (starting from the nitrogen atom to which the radical R 5 is attached) longest carbon chain of the alkyl radical, i.e. in the ⁇ -position to the nitrogen atom, and optionally a further branching point at a further carbon atom of the alkyl group, in particular at the 2-position of the longest carbon chain of the alkyl radical.
  • Examples of these are isopropyl, sec-butyl, tert-butyl, 1-methylpropyl, 2-pentyl, 2-methylbutyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, 2-hexyl, 2-methylpentyl, 1 ,2,2-trimethylpropyl and the like.
  • the straight-chain or branched C2-Cs-haloalkyl radical is preferably a fluorinated C2-C8- alkyl radical.
  • the fluorinated C2-Cs-alkyl radical preferably has 1 , 2, 3, 4, 5 or 6 fluorine atoms, particularly preferably 1 , 2 or 3 and especially 2 or 3 fluorine atoms.
  • the fluorine atoms are not attached to the carbon atom of the haloalkyl radical which is attached directly to the nitrogen atom which carries the radical R 5 .
  • the fluorine atoms are attached in the 2- and/or 3-position of the (starting from the nitrogen atom to which the radical R 5 is attached) longest carbon chain of the haloalkyl radical.
  • the branched Cs-Cs-haloalkyl radical has a branching point at the 1 -position of the (starting from the nitrogen atom to which the radical R 5 is attached) longest carbon chain of the haloalkyl radical, i.e. at the ⁇ -position to the nitrogen atom, and optionally a further branching point at a further carbon atom of the haloalkyl group, for example at the 2- and/or 3-position of the longest carbon chain of the haloalkyl radical.
  • the straight-chain or branched C2-C8-haloalkyl radical is especially a fluorinated C2-C3- alkyl radical, for example 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-fluoro-i- methylethyl, 2,2-difluoro-1 -methylethyl, 1 -methyl-2,2,2-trifluoroethyl, bis(fluoromethyl)methyl, bis(difluoromethyl)methyl, bis(trifluoromethyl)methyl and the like.
  • a fluorinated C2-C3- alkyl radical for example 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-fluoro-i- methylethyl, 2,2-difluoro-1 -methylethyl, 1 -methyl-2,2,2-trifluoroethyl, bis(flu
  • R 6 is preferably H or has one of the inventive or preferred meanings given for R 5 .
  • R 6 is H or Ci-C4-alkyl, more preferably H, methyl or ethyl and in particular H or methyl.
  • R 6 is H.
  • R 5 is preferably different from H.
  • R 6 is #-CR 61 R 62 -(CR 63 R 64 ) q -(CR 65 R 66 )p-Y-Z in which # is the point of attachment to the nitrogen atom and R 61 , R 62 , R 63 , R 64 , R 65 , R 66 , Y, Z, p and q have the general meanings given above or the preferred meanings given below.
  • R 5 is preferably H or Ci-C4-alkyl, more preferably H, methyl or ethyl and in particular H or methyl. In a special embodiment of the invention, R 5 is in this case H.
  • R 61 is preferably straight-chain or branched Ci-Cs-alkyl, Cs-Cs-alkenyl or C3-C6- cycloalkyl, particularly preferably d-C ⁇ -alkyl or Cs-C ⁇ -cycloalkyl, for example methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, sec-pentyl, cyclopropyl or cyclopentyl, preferably isopropyl, isobutyl, tert-butyl, sec-pentyl, cyclopropyl or cyclopentyl and in particular tert-butyl.
  • R 61 is not hydrogen or methyl.
  • the group R 61 has a branching point at the ⁇ -carbon atom.
  • the group R 61 is substituted by groups attached via heteroatoms, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or formyl, carboxyl, alkoxycarbonyl, alkoxythiocarbonyl or alkenyl, alkynyl groups or C2-Cs-alkylene, where both valencies are attached to the same carbon atom.
  • the group R 61 is substituted by Cs-C ⁇ -cycloalkyl or Cs-Cs-cycloalkenyl.
  • the group R 61 is substituted by C(O)R A , C(O)OR A , C(S)OR A , C(O)NR A R B , C(S)NR A R B , C(NR A )R B , C(O)SR ⁇ or C(S)SR ⁇ .
  • R ⁇ is preferably d-Cs-alkyl or Cs-C ⁇ -cycloalkyl, where these groups may be partially or fully halogenated.
  • the group R 61 is substituted by a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S.
  • R 62 is hydrogen, straight-chain or branched Ci-Cs-alkyl or Cs-C ⁇ -cycloalkyl, in particular hydrogen, Ci-C ⁇ -alkyl or Cs-C ⁇ -cycloalkyl, preferably hydrogen, isopropyl or tert-butyl. If R 62 is an alkyl group, R 62 preferably has the same meaning as R 61 .
  • R 61 and R 62 together form a Cs-C ⁇ -alkylene, in particular a C3-C4-alkylene, group, where the carbon chains may be substituted by the groups attached via heteroatoms, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or alkoxycarbonyl.
  • R 61 and R 62 together form a Cs-C ⁇ -alkylene, in particular a C3-C4-alkylene, group, where the carbon chains are interrupted by one or two heteroatoms from the group consisting of O, N and S and may be substituted by groups attached via heteroatoms, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or alkoxycarbonyl.
  • R 62 , R 63 , R 64 , R 65 and R 66 are each hydrogen or Ci-C4-alkyl, preferably hydrogen, methyl or ethyl, in particular hydrogen.
  • the substitution of the groups R 62 , R 63 , R 64 , R 65 and R 66 corresponds preferably to that of the group R 61 .
  • R 61 and R 63 together form a Cs-C ⁇ -alkylene, C3-C6-oxyalkylene or C2-C5-oxyalkyleneoxy, in particular a C3-C4-alkylene, group.
  • R 63 and R 64 and/or R 65 and R 66 in each case together form a Cs-C ⁇ -alkylene, Cs-C ⁇ -oxyalkylene or C2-C5-oxyalkyleneoxy, in particular a C3-C4-alkylene, group.
  • the index q has the value zero or 1.
  • the index p is zero or 1 , in particular zero.
  • R 63 and R 64 are preferably hydrogen if the index p has the value zero.
  • R 65 is not hydrogen and R 66 is hydrogen if the index p is not zero.
  • the index p has the value zero or 1 and the index q has the value 1.
  • R 65 and R 66 are preferably hydrogen. In an alternative preferred embodiment, R 65 is not hydrogen and R 66 is hydrogen.
  • Y is oxygen
  • Z is a monovalent group.
  • Z is selected from the group consisting of Ci-d-alkyl- carbonyl, in particular acetyl, n-propan-1-one, 2-methylpropan-1-one or butan-1-one, hydrogen, carboxyl, formyl, d-Cs-alkyl, d-Cs-haloalkyl, C2-C8-alkenyl, C2-C8- haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, Cs-drcycloalkyl, Cs-Cs-cycloalkenyl, C(O)R ⁇ , C(O)OR ⁇ , C(S)OR ⁇ , C(O)SR ⁇ , C(S)SR ⁇ , C(NR A )SR ⁇ , C(S)R ⁇ ,
  • the abovementioned groups Z can be substituted by one or more groups R b1 .
  • the group Z is substituted by one, two, three or four groups R b1 , such as halogen, or basic or acidic groups, such as NR A R B , guanidyl, amidyl, hydroxyl, carboxyl or sulfonic acids.
  • Z is especially selected from the group consisting of H, formyl, d-d-alkylcarbonyl and Cs-drcycloalkylcarbonyl.
  • the groups R A and R B are hydrogen, d-d-alkyl or d-d-haloalkyl, in particular hydrogen and methyl.
  • R ⁇ is preferably d-d-alkyl or d-d-haloalkyl, in particular methyl.
  • R 61 is H or d-d-alkyl
  • R 62 is H
  • R 63 is H or d-d-alkyl
  • R 64 is H
  • q is 0 or 1 , in particular 1
  • p is 0,
  • Y is O and Z is H
  • R 5 is preferably H, Ci-C ⁇ -alkyI or d-Cs-haloalkyl, particularly preferably H, d-d-alkyl or d-d-haloalkyl and in particular H or Ci-d-alkyl.
  • the group NR 5 R 6 is ethylglycinol, leucinol, tert-leucinol, valinol, norvalinol, methioninol, phenylalaninol, lysinol, argininol, histidinol, asparaginol, glutaminol, serinol, isoleucinol, cysteinol, hydroxymethylpiperidine, cis-2-hydroxymethyl-4-methylpiperidine, trans-2-hydroxy- methyl-4-methylpiperidine, cyclohexylglycinol, cyclopentylglycinol, butylglycinol, pentylglycinol, cis-2-aminocyclohexanol, trans-2-aminocyclohexanol, cis-2-aminocyclo- pentanol, trans-2-aminocyclopentano
  • neither R 5 nor R 6 is H, i.e. the radical R 1 is a tertiary amine.
  • R 5 and R 6 together with the nitrogen atom to which they are attached form a saturated or unsaturated 5- or 6-membered heterocycle, where the heterocycle may additionally contain a heteroatom or a heteroatom-containing group selected from the group consisting of O, N and NR'" as ring member, where R'" is H, d-Cs-alkyl, d-Cs-haloalkyl or C2-C8-hydroxyalkyl and in particular H or Ci-C ⁇ -alkyl, and where the heterocycle may carry 1 , 2 or 3 substituents selected from the group consisting of halogen, hydroxyl, d-Cs-alkyl, d-Cs-haloalkyl, C2-C8-hydroxyalkyl, d-Cs-alkoxy, and d-Cs-haloalkoxy.
  • the heterocycle may additionally contain a heteroatom or a heteroatom-containing group selected from the group consisting of O, N and NR'" as ring member, where R'"
  • R 5 and R 6 together with the nitrogen atom to which they are attached form a saturated 5- or, in particular, 6-membered heterocycle, where the heterocycle may additionally contain a heteroatom or a heteroatom-containing group selected from the group consisting of O and NR"' as ring member, where R'" is H, d-Cs-alkyl, Ci-Cs- haloalkyl or C2-C8-hydroxyalkyl and in particular H or Ci-C ⁇ -alkyl, and where the hetreocycle may carry 1 or 2 substituents selected from the group consisting of halogen, hydroxyl, d-Cs-alkyl, d-Cs-haloalkyl, C2-C8-hydroxyalkyl, Ci-Cs-alkoxy and d-C ⁇ -haloalkoxy.
  • the heterocycle may additionally contain a heteroatom or a heteroatom-containing group selected from the group consisting of O and NR"' as ring member, where R'" is H, d-
  • the heterocycle has, in addition to the nitrogen atom which carries the radicals R 5 and R 6 , no further heteroatoms as ring members.
  • substituents these are preferably selected from the group consisting of halogen, d-d-alkyl and d-d-haloalkyl and in particular from the group consisting of d-d-alkyl.
  • the heterocycle carries a d-d-alkyl substituent, for example a methyl substituent.
  • R 1 is a radical OR 9 .
  • R 9 is preferably not H.
  • R 9 is d-C 6 -alkyl, d-Ce-haloalkyl, C 2 -C 6 - alkenyl, C2-C6-alkynyl or Cs-C ⁇ -cycloalkyl.
  • R 9 is Ci-C ⁇ -alkyl, C2-C6-alkenyl or d-C ⁇ -haloalkyl which are in each case branched at the ⁇ -position.
  • R 9 is particularly preferably d-d-haloalkyl.
  • R 9 is in particular ethyl, propyl, isopropyl, 1 ,2-dimethylpropyl, 1 ,2,2-trimethylpropyl, 1-methyl-2,2,2-trifluoroethyl or 2,2,2-trifluoroethyl.
  • R 1 is a group R 1 ' or a group NR 5 R 6 , where R 1 ', R 5 and R 6 preferably have the preferred meanings given above.
  • R 1 is in particular a group R 1 ', where R 1 ' preferably has the preferred meanings given above.
  • the radical R 2 is phenyl, pyridinyl, for example 2-, 3- or 4-pyridinyl, pyrimidinyl, for example 2-, 4- or 5-pyrimidinyl, pyrazinyl, for example 2-pyrazinyl, pyridazinyl, for example 3- or 4-pyridazinyl, triazinyl, furyl, for example 2- or 3-furyl, thienyl, for example 2- or 3-thienyl, pyrrolyl, for example 2- or 3-pyrrolyl, pyrazolyl, for example 1-, 3-, 4- or 5-pyrazolyl, imidazolyl, for example 1-, 2-, 4- or 5-imidazolyl, oxazolyl, for example 2-, 4- or 5-oxazolyl, isoxazolyl, for example 3-, 4- or 5-isoxazolyl, thiazolyl, for example 2-, 4- or 5-thiazolyl, isothiazolyl, for example
  • the radical R 2 is phenyl, pyridinyl, for example 2-, 3- or 4- pyridinyl, pyrimidinyl, especially 4- or 5-pyrimidinyl, pyrazinyl, for example 2-pyrazinyl, pyridazinyl, for example 3- or 4-pyridazinyl, furyl, for example 2- or 3-furyl, thienyl, for example 2- or 3-thienyl, pyrazolyl, especially 1- or 5-pyrazolyl, imidazolyl, especially 1-, 2- or 5-imidazolyl, oxazolyl, for example 2-, 4- or 5-oxazolyl, isoxazolyl, for example 3-, 4- or 5-isoxazolyl, thiazolyl, for example 2-, 4- or 5-thiazolyl, isothiazolyl, for example 3-, 4- or 5-isothiazolyl, or triazolyl, especially 1-[1 ,2,4]-1 H-triazolyl which
  • R 2 is phenyl substituted by a radical L 1 and 1 , 2, 3 or 4, preferably 1 or 2 radicals L 2 .
  • L 2 is preferably selected from halogen, Ci-Cs-alkyl, for example Ci-C4-alkyl, Ci-Cs- haloalkyl, for example Ci-C4-haloalkyl, Ci-Cs-alkoxy, for example Ci-C4-alkoxy, Ci-Cs- haloalkoxy, for example Ci-C4-haloalkoxy, cyano, nitro, Ci-C4-alkoxycarbonyl, and aminocarbonyl.
  • Ci-Cs-alkyl for example Ci-C4-alkyl
  • Ci-Cs- haloalkyl for example Ci-C4-haloalkyl
  • Ci-Cs-alkoxy for example Ci-C4-alkoxy
  • Ci-Cs-haloalkoxy for example Ci-C4-haloalkoxy
  • L 2 is selected from d-Cs-alkyl, for example Ci-C 4 - alkyl, d-Cs-haloalkyl, for example d-d-haloalkyl, Ci-Cs-alkoxy, for example C1-C4- alkoxy, and Ci-Cs-haloalkoxy, for example Ci-C4-haloalkoxy.
  • L 2 is selected from halogen, such as fluorine or chlorine, Ci-C4-alkyl, such as methyl, Ci-C4-haloalkyl, such as trifluoromethyl, and Ci-C4-alkoxy, such as methoxy.
  • L 2 is selected from halogen, in particular fluorine or chlorine, C1-C4- alkyl, in particular methyl, and Ci-C4-alkoxy, in particular methoxy.
  • L 2 is selected from halogen and Ci-C4-alkyl and is especially halogen, such as chlorine or fluorine, or methyl.
  • L 2 is chlorine or fluorine and specifically fluorine.
  • Embodiments of the radical R 2 relate in particular to phenyl groups which, in addition to the group L 1 , may have the following substituents: position 2: fluorine, chlorine, methyl, preferably fluorine or chlorine, in particular fluorine; position 3: hydrogen, fluorine, methoxy, the group L 1 ; preferably hydrogen or the group L 1 ; position 5: hydrogen, fluorine, chlorine, methyl, the group L 1 ; particularly preferably hydrogen or the group L 1 ; position 6: hydrogen, fluorine, chlorine, methyl; particularly preferably hydrogen or fluorine.
  • the radical L 1 is preferably located in position 3, 4 or 5 (relating to the attachment point of R 2 to the pyrazine moiety as position 1).
  • R 2 is one of the groups A or B, group A being more preferred.
  • L 2 is preferably one of the following substituent combinations: 2-CI; 2-F; 2-CH3; 6-CI; 6-F; 6-CH 3 ; 2,6-F 2 ; 2,6-Cl 2 ; 2-F,6-CH 3 ; 2-CH 3 ,6-F; 2-CF 3 , 6-F; 2-OCH 3 ,6-F; 2-F.6-
  • L 2 is one of the following substituent combinations: 2-F; 2-CI; 2-
  • R 2 is 5-membered heteroaryl which is substituted by a radical L 1 and by 1 , 2 or 3 radicals L 2 .
  • the 5-membered heteroaryl ring is preferably selected from the group consisting of thienyl, for example 2- or 3-thienyl, pyrazolyl, for example 1-, 3-, 4- or 5-pyrazolyl, and thiazolyl, for example 2-, 4- or 5-thiazolyl.
  • R 2 is 6-membered heteroaryl which contains 1 to 3 nitrogen atoms and is substituted by a radical L 1 and by 1 , 2 or 3 radicals L 2 .
  • the 6-membered heteroaryl ring is preferably selected from the group consisting of pyridinyl, for example 2-, 3- or 4-pyridinyl, pyrimidinyl, for example 2-, 4- or 5-pyrimidinyl, pyrazinyl, for example 2-pyrazinyl, and pyridazinyl, for example 3- or 4-pyridazinyl.
  • R 2 is pyridyl which is attached in the 2-, 3- or 4-position to the pyrazine ring and carries 1 , 2 or 3 identical or different substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano,
  • R 2 is pyrimidyl which is attached in the 2- or 4-position to the pyrazine ring and carries 1 or 2 identical or different substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl
  • R 2 is thienyl which is attached in the 2- or 3-position to the pyrazine ring and carries 1 or 2 identical or different substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl,
  • R 2 is thiazolyl which is attached in the 2-, 4- or 5-position to the pyrazine ring and carries a substituent L 2 which is preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • L 2 is preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • L 2 is preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy,
  • R 2 is imidazolyl which is attached in the 4- or 5-position to the pyrazine ring and carries 1 or 2 identical or different substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl,
  • R 2 is pyrazolyl which is attached in the 1-, 3-, 4- or 5-position to the pyrazine ring and carries 1 or 2 identical or different substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro
  • R 2 is oxazolyl which is attached in the 2-, 3- or 4-position to the pyrazine ring and carries a substituent L 2 which is preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • L 2 is preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • L 2 is preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy,
  • At least one group L 2 is located in the ortho-position to the point of attachment of the group R 2 to the pyrazine skeleton, in particular chlorine, fluorine or methyl.
  • a heteroatom of the heteroaromatic radical R 2 is located in the ortho-position to the point of attachment.
  • the index m is preferably 1 to 4, where the groups L 2 may be identical or different.
  • the heteroaromatic groups R 2 carry, in addition to a group L 1 , further substituents L 2 , these are preferably selected from the group consisting of: fluorine, chlorine, methyl, methoxy, cyano, nitro, alkoxycarbonyl, aminocarbonyl and haloalkyl.
  • the substituents L 2 are selected from the group consisting of fluorine, chlorine, methyl and methoxy.
  • the substituents L 2 are selected from the group consisting of fluorine, chlorine and methyl.
  • a further embodiment relates to heteroaromatic groups R 2 which, in addition to a group L 1 , are substituted by fluorine.
  • the radical R 2 is in particular phenyl or pyridinyl, especially phenyl, where these carry a substituent L 1 and 1 , 2, 3 or 4, preferably 1 or 2, in particular 1 or 2, substituents L 2 , where L 1 and L 2 are defined as above or as described below.
  • R 2 is phenyl or 2-pyridinyl
  • these rings preferably carry the substituent L 1 in the 3-, 4- or 5-position, the 4-position being more preferred (based on the 1 -position of the bond to the pyrazine ring; i.e. L 1 is particularly preferably attached in the meta- or, in particular, para-position to this point of attachment).
  • the phenyl or the 2-pyridinyl ring has 1 or 2 further substituents L 2 . These are preferably attached in the 2- and/or 6- position of the phenyl ring (based on the 1 -position of the bond to the pyrazine ring), i.e. in the ortho-position to the point of attachment to the pyrazine ring, and in the case of the 2-pyridine ring preferably attached in the 6-position (based on the 1 -position of the bond to the pyrazine ring).
  • each L 2 is preferably bound in ortho position to the attachment point of the phenyl ring to the pyrazine moiety.
  • the substituent L 1 of the radical R 2 is is a group of the formula -Y 1 -Y 2 -T in which
  • Y 1 is CR h R', C(O)O, C(O)NR h , O, NR h or S(O) r ;
  • Y 2 is d-Cs-alkylene, C2-Cs-alkenylene or C2-C8-alkynylene, where Y 2 may be interrupted by one, two, three or four heteroatoms from the group consisting of NR h , O and S(O) r ; r is O, 1 or 2;
  • the substituent L 1 of the radical R 2 is a radical L 11 of the formula in which
  • a ⁇ is Ci-C 4 -alkylene; ⁇ ⁇ 1 ⁇ ⁇ 2 j n( j e p enc
  • R h ⁇ and R' ⁇ independently of one another are H or Ci-C4-alkyl; and a is 1 , 2, 3 or 4.
  • Ci-C4-Alkylene in A ⁇ is preferably methylene, 1 ,2-ethylene, 1 ,2- or 1 ,3-propylene or 1 ,4-n-butylene.
  • a ⁇ is preferably methylene, 1 ,2-ethylene, 1 ,2-propylene or 1 ,3-propylene and in particular methylene or 1 ,2-ethylene.
  • ⁇ «i and ⁇ ⁇ 2 independently of one another are preferably O or NR hCt . If YTM 1 is O, YTM 2 is also preferably O. Moreover, in this case T ⁇ is preferably 0R hCt . If Y 0 " 1 is NR hCt R' ⁇ and YTM 2 is simultaneously O, T ⁇ is in this case preferably 0R h ⁇ .
  • T is preferably 0R h ⁇ or NR hCt R' ⁇ .
  • R h ⁇ and R' ⁇ independently of one another are preferably H, methyl or ethyl.
  • a is preferably 1 , 2 or 3.
  • R 2 is a radical L 12 of the formula Y ⁇ -A ⁇ -T ⁇ in which
  • Y ⁇ is CH 2 , O, S or NR h ⁇ R
  • a ⁇ is C-i-Cs-alkylene
  • T ⁇ is 0R h ⁇ , NR h ⁇ R
  • ⁇ or OC( O)- " P ⁇ ;
  • T 3 ⁇ is R h ⁇ , 0R h ⁇ or NR h ⁇ R
  • ⁇ is independently H or Ci-C 4 -alkyl.
  • Y ⁇ is preferably CH 2 or O and especially O.
  • a ⁇ is preferably d-C ⁇ -alkylene, in particular Ci-C 4 -alkylene.
  • T ⁇ is preferably 0R h ⁇ or NR h ⁇ R
  • ⁇ independently of one another are preferably H, methyl or ethyl and specifically methyl.
  • the substituent L 1 of the radical R 2 is a radical L 13 of the formula
  • Y 17 is -CONR h7 Or -COO;
  • a ⁇ is C 2 -C 6 -alkylene;
  • T 3 ⁇ is R h ⁇ , 0R h ⁇ or NR h ⁇ R' ⁇ ; and each R h ⁇ and R' ⁇ is independently H or Ci-C4-alkyl.
  • the substituent L 1 of the radical R 2 is a radical L 11 or L 12 and specifically L 12 .
  • R 3 is preferably halogen, Ci-Cio-alkyl, especially d-Cs-alkyl, Ci-Cio-haloalkyl, especially d-Cs-haloalkyl, Ci-Cio-alkoxy, especially d-Cs-alkoxy, Ci-Cio-haloalkoxy, especially d-Cs-haloalkoxy, or CN, particularly preferably halogen, d-d-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or CN, more preferably halogen, d-d-alkyl, especially Ci-C2-alkyl, or Ci-C4-haloalkyl, especially Ci-C2-haloalkyl.
  • R 3 is in particular halogen, especially chlorine, or d-d-alkyl, especially Ci-C2-alkyl, in particular methyl, and specifically halogen, especially chlorine.
  • R 4 is a radical R 4a which for its part is a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered, preferably 5- or 6-membered, saturated, partially unsaturated or aromatic heterocyclic ring having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members, where the heterocyclic ring may be partially or fully halogenated and/or may carry 1 , 2 or 3 radicals R x , where R x is as defined above.
  • the 5- or 6-membered heterocycles are preferably selected from the group consisting of pyrrolyl, such as 1-, 2- and 3-pyrrolyl; pyrrolinyl, such as 1-, 2- and 3-pyrrolinyl; pyrrolinonyl, pyrrolidinyl, such as 1-, 2- and 3-pyrrolidinyl; pyrrolidonyl, such as 1-, 3-, 4- and 5-pyrrolidin-2-onyl and also 1-, 2-, 4- and 5-pyrrolidin-3-onyl; pyrrolidindionyl, such as 1-pyrrolidin-2,5-dionyl; pyrazolyl, such as 1-, 3-, 4- and 5-pyrazolyl; pyrazolinyl, such as 1-, 3-, 4- and 5-pyrazolinyl; pyrazolidinyl, such as 1-, 2-, 3- and 4-pyrazolidinyl; pyrazolidinonyl; imidazolyl, such as 1-, 2-, 4- and 5-imid
  • oxazolinyl such as 2-, 4- and 5-oxazolinyl
  • oxazolidinyl such as 2-, 3-, 4- and 5-oxazolidinyl
  • oxazolidinonyl such as 3-, 4- and 5-oxazolidin-2-onyl
  • isoxazolyl such as 3-, 4- and 5-isoxazolyl
  • isoxazolinyl such as 3-, 4- and 5-isoxazolinyl
  • isoxazolidinyl such as 3-, 4- and 5-isoxazolidinyl
  • isoxazolidinonyl such as 2-, 4- and 5-isoxazolidin-3-onyl
  • thiadiazolyl such as 4- and 5-[1 ,2,3]-thiadiazolyl, 3- and 5-[1 ,2,4]-thiadiazolyl and also 2- and 5-[1 ,3,4]-thiadiazolyl
  • oxadiazolyl such as 4- and 5-[1
  • the heterocyclic ring is unsubstituted or carries 1 or 2 substituents R x selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy and in particular from the group consisting of nitro and Ci-C4-alkyl, especially nitro, methyl or ethyl.
  • R x selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy and in particular from the group consisting of nitro and Ci-C4-alkyl, especially nitro, methyl or ethyl.
  • the radical R 4a is a 5- or 6-membered heteroaromatic ring which contains a nitrogen atom and optionally one or two further heteroatoms selected from the group consisting of O, N and S as ring members and which may be partially or fully halogenated and/or carry 1 , 2 or 3 radicals R x , where R x has the inventive or preferred meanings mentioned above (radical R 4aa ).
  • R 4aa is pyrrolyl, such as 1-, 2- and 3-pyrrolyl; pyrazolyl, such as 1-, 3-, 4- and 5-pyrazolyl; imidazolyl, such as 1-, 2-, 4- and 5-imidazolyl; triazolyl, 1- and 2-[1 ,3,5]-(1 H)-triazolyl, 1-, 4- and 5-[1 ,2,3]-1 H-triazolyl, 2-, 4 and 5-[1 ,2,3]-2H-triazolyl and also 1-, 3- and 5-[1 ,2,4]-(1 H)-triazolyl; tetrazolyl, such as 1- and 5-[1 ,2,3,4]-(1 H)- tetrazolyl; thiazolyl, such as 2-, 4- and 5-thiazolyl; isothiazolyl, such as 3-, 4- and 5-isothiazolyl; oxazolyl, such as 2-, 4- and 5-oxazolyl; isoxazolyl
  • R 4aa is a 5-membered heteroaromatic ring which contains a nitrogen atom and optionally one or two further heteroatoms selected from the group consisting of O, N and S as ring members, such as pyrrolyl, such as 1-, 2- and 3- pyrrolyl; pyrazolyl, such as 1-, 3-, 4- and 5-pyrazolyl; imidazolyl, such as 1-, 2-, 4- and 5-imidazolyl; triazolyl, 1- and 2-[1 ,3,5]-(1 H)-triazolyl, 1-, 4- and 5-[1 ,2,3]-1 H-triazolyl, 2-, 4 and 5-[1 ,2,3]-2H-triazolyl and also 1-, 3- and 5-[1 ,2,4]-(1 H)-triazolyl; tetrazolyl, such as 1- and 5-[1 ,2,3,4]-(1 H)-tetrazolyl; thiazolyl, such as 2-, 4- and 5-
  • nitrogen-bound rings such as 1-pyrrolyl, 1- pyrazolyl, 1-imidazolyl, 1- and 2-[1 ,2,3]-triazolyl, 1- and 2-[1 ,2,4]-triazolyl, and 1- or 2- [1 ,2,3,4]-tetrazolyl.
  • R 4 is pyrazol-1-yl.
  • R 4aa is preferably unsubstituted or carries 1 or 2 identical or different substituents R x , which are as defined above or, preferably, selected from the group consisting of halogen, nitro, Ci-C4-alkyl and Ci-C4-haloalkyl and in particular from the group consisting of nitro and Ci-C4-alkyl, especially methyl. Specifically, R 4aa is unsubstituted.
  • the radical R 4a is a 5- or 6-membered saturated or partially unsaturated nonaromatic heterocyclic ring which contains a nitrogen atom and optionally one or two further heteroatoms selected from the group consisting of O, N and S and/or one or two carbonyl groups as ring members and which may be partially or fully halogenated and/or carry 1 , 2 or 3 radicals R x , where R x has the inventive or preferred meanings mentioned above (radical R 4ab ).
  • R 4ab is preferably a saturated heterocyclic radical selected from the group consisting of pyrrolidinyl, such as 1-, 2- and 3-pyrrolidinyl; pyrrolidonyl, such as 1-, 3-, 4- and 5-pyrrolidin-2-onyl and also 1-, 2-, 4- and 5-pyrrolidin-3-onyl; pyrrolidindionyl, such as 1-pyrrolidin-2,5-dionyl; pyrazolidinyl, such as 1-, 2-, 3- and 4-pyrazolidinyl; pyrazolidinonyl; imidazolidinyl, such as 1-, 2- and 4-imidazolidinyl; imidazolidinonyl, such as 1- and 4-imidazolidin-2-onyl and also 1-, 2-, 3- and 5-imidazolidin-4-onyl; thiazolidinyl, such as 2-, 4- and 5-thiazolidinyl; isothiazoidinlyl, such as 3-, 4- and 5-is
  • R 4ab is a partially unsaturated heterocyclic radical.
  • Examples of partially unsaturated (nonaromatic) heterocycles are pyrrolinyl, such as 1-, 2- and 3-pyrrolinyl; pyrrolinonyl, pyrazolinyl, such as 1-, 3-, 4- and 5-pyrazolinyl; imidazolinyl, such as 1-, 2-, 4- and 5-imidazolinyl; thiazolinyl, such as 2-, 4- and 5-thiazolinyl; isothiazolinyl, such as 3-, 4- and 5-isothiazolinyl; oxazolinyl, such as 2-, 4- and 5-oxazolinyl; isoxazolinyl, such as 3-, 4- and 5-isoxazolinyl; dihydropyridyl, such as 1 ,4-dihydropyrid-1-, 2-, 3- and 4-yl; dihydropyridinonyl, such as 1-, 3-, 4-, 5- and 6-(1 ,2-dihydro
  • R 4ab is pyrrolidonyl, such as 1-, 3-, 4- and 5-pyrrolidin-2-onyl and also 1-, 2-, 4- and 5-pyrrolidin-3-onyl; imidazolidinonyl, such as 1- and 4-imidazolidin-2- onyl and also 1-, 2-, 3- and 5-imidazolidin-4-onyl; oxazolidinonyl, such as 3-, 4- and 5-oxazolidin-2-onyl; isoxazolidinonyl, such as 2-, 4- and 5-isoxazolidin-3-onyl; or dihydropyridinonyl, such as 1-, 3-, 4-, 5- and 6-(1 ,2-dihydro)pyridin-2-onyl, where the heterocyclic rings may be partially or fully halogenated and/or carry 1 , 2 or 3 radicals R x , where R x has the inventive or preferred meanings given above or below.
  • R 4ab is preferably unsubstituted or carries 1 or 2 identical or different substituents R x which are as defined above or, preferably, selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl and in particular from the group consisting of Ci-C4-alkyl, especially methyl.
  • R 4ab is pyrazolinyl, especially 2-pyrazolinyl, which is unsubstituted or carries 1 or 2 identical or different substituents R x which are preferably selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl and in particular from the group consisting of Ci-C4-alkyl, especially methyl.
  • R 4 is a radical R 4c which for its part is a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered, preferably 5- or 6-membered, saturated, partially unsaturated or aromatic heterocyclic ring having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members, hich is fused to a phenyl ring, where the fused system may be partially or fully halogenated and/or may carry 1 , 2 or 3 radicals R x , where R x is as defined above.
  • the fused system is preferably selected from benzimidazolyl, benzothiazolyl, quinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl and benzotriazinyl.
  • R 4b , R a , R b , R c , R d , R e and R f are preferably selected from the group consisting of H, hydroxyl, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxy, where, if R a , R b , R c or R d are attached directly to an oxygen atom, they are not hydroxyl or Ci- C4-alkoxy.
  • R 4b , R a , R b and R c are particularly preferably selected from the group consisting of H, hydroxyl, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxy, where, if R a , R b or R c are attached directly to an oxygen atom, they are not hydroxyl or C1-C4- alkoxy, and R d , R e and R f are selected from the group consisting of H and Ci-C4-alkyl.
  • X 2 is preferably a bond or -CO- and in particular a bond.
  • X 2 is a single bond, -CO-, -CONH-, -COO-, -O- or -NR f , where the left part of the divalent radicals is attached to the nitrogen atom;
  • R a is hydrogen, hydroxyl, Ci-C4-alkyl, Ci-C4-alkoxy or Ci-C4-alkylcarbonyl;
  • R b , R c , R d , R e and R f independently of one another are hydrogen, hydroxyl, Ci-C4-alkyl or Ci-C4-alkoxy, where, if R a , R b , R c or R d are attached directly to an oxygen atom, they are not hydroxyl or Ci-C4-alkoxy.
  • R 4ba , R b and R c are particularly preferably selected from the group consisting of H, hydroxyl, Ci-C4-alkyl and Ci-C4-alkoxy and R a is selected from the group consisting of H, hydroxyl, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxy, where, if R a , R b or R c are attached directly to an oxygen atom, they are not hydroxyl or Ci-C4-alkoxy, and R d , R e and R f are selected from the group consisting of H and C1-C4- alkyl.
  • X 2 is preferably a bond or -CO- and in particular a bond.
  • R 4 is a radical R 4c of the formula -NR a R b , -NR c NR a R b , -NR a -CN, -CR a R b -OR c , -CR a R b -SR c or -CR a R b -NR c R d , where R a , R b , R c and R d are as defined above.
  • R a , R b , R c and R d are preferably independently H, Ci-C4-alkyl or Ci-C4-alkoxy and in particular H or Ci-C4-alkyl.
  • R 4 is a radical R 4d of the formula
  • x is O or i ;
  • X 1 and X 11 are independently oxygen or N-R f ;
  • Q is C(H)-R', C-R' , N-N(H)-R f or N-R f ;
  • 1 ⁇ - is a single bond or a double bond
  • R a , R b , R c , R f independently of one another are hydrogen, Ci-C ⁇ -alkyl, C2-C8-alkenyl, C2-C8-alkynyl, Cs-C ⁇ -cycloalkyl or C4-C6-cycloalkenyl, or
  • R 9 , R s and R 1 are defined like R c and may furthermore be halogen or cyano; or
  • R a , R b , R c , R f , R 9 , R s and/or R 1 may be partially or fully halogenated and/or carry 1 , 2, 3 or 4 substituents R v , where
  • R v is halogen, cyano, d-Cs-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, C-i-C ⁇ -alkoxy, C2-Cio-alkenyloxy, C2-Cio-alkynyloxy, Cs-C ⁇ -cycloalkyl, Cs-C ⁇ -cycloalkenyl, C3-C6-cycloalkoxy or Cs-C ⁇ -cycloalkenyloxy, or two of the radicals R a , R b ,
  • R c or R d together with the atoms to which they are attached form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocycle having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of N, O and S.
  • R 4 is a radical R 4e of the formula
  • X 2 is a single bond, -CO-, -CONH-, -COO-, -O- or -NR f -, where the left part of the divalent radicals is attached to the nitrogen atom;
  • R f is hydrogen, methyl or Ci-C4-alkylcarbonyl
  • R b is hydrogen, methyl, benzyl, trifluoromethyl, allyl, propargyl or methoxymethyl;
  • R b# , R d# are independently hydrogen, d-Ce-alkyl or C 2 -C 6 -alkynyl;
  • W is S or NR d# ;
  • R w is halogen, OR Z , NHR Z , Ci-C 6 -alkyl, Ci-C 4 -alkoxycarbonyl, Ci-C 4 -acylamino, [1 ,3]dioxolane-Ci-C4-alkyl or [1 ,3]dioxane-Ci-C4-alkyl in which R z is hydrogen, methyl, allyl or propargyl.
  • radicals R 4 preference is given to radicals R 4a and especially to R 4a
  • radicals R 4aa preference is given to what has been said above.
  • a particular embodiment of the invention relates to compounds of the formulae 1.1.1 and 1.1.2
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 , in particular a radical L 11 or L 12 and specifically L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
  • Ci-C4-alkoxy or Ci-C4-haloalkoxy preferably H, halogen or Ci-C4-alkyl, and more preferably H or halogen, where at least one of the radicals L 2a , L 2b is not H;
  • R 3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen;
  • R 4a has the meanings given above and is preferably a radical R 4aa or R 4ab and more preferably R 4aa ; and
  • R 5 and R 6 have the meanings given above, preferably the meanings given as being preferred.
  • a further particular embodiment of the invention relates to compounds of the formulae 1.2.1 and I.2.2
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 , in particular a radical L 11 or L 12 and specifically L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, and more preferably H or halogen, where at least one of the radicals L 2a , L 2b is not H;
  • R 3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen;
  • R 4b' is CN or a radical R 4b which has the general or preferably preferred meanings given above and is preferably CN or a radical R 4ba ;
  • R 5 and R 6 have the meanings given above, preferably the meanings given as being preferred.
  • a further particular embodiment of the invention relates to compounds of the formulae 1.3.1 and I.3.2
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 , in particular a radical L 11 or L 12 and specifically L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
  • R 3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen;
  • R 4c has the general or preferably preferred meanings given above; and R 5 and R 6 have the meanings given above, preferably the meanings given as being preferred.
  • a further particular embodiment of the invention relates to compounds of the formulae 1.4.1 and I.4.2
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 , in particular a radical L 11 or L 12 and specifically L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
  • R 3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen;
  • R 4d has the general or preferably preferred meanings given above; and R 5 and R 6 have the meanings given above, preferably the meanings given as being preferred.
  • a further particular embodiment of the invention relates to compounds of the formulae 1.5.1 and I.5.2
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 , in particular a radical L 11 or L 12 and specifically L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
  • R 3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen;
  • R 4e has the general or preferably preferred meanings given above; and R 5 and R 6 have the meanings given above, preferably the meanings given as being preferred.
  • a further particular embodiment of the invention relates to compounds of the formulae 1.6.1 and I.6.2
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 , in particular a radical L 11 or L 12 and specifically L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
  • R 1 ' has the meanings given above, preferably the meanings given as being preferred;
  • R 3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen; and
  • R 4a has the meanings given above and is preferably a radical R 4aa or R 4ab and more preferably R 4aa .
  • a further particular embodiment of the invention relates to compounds of the formulae 1.7.1 and I.7.2
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 , in particular a radical L 11 or L 12 and specifically L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, preferably H or halogen, where at least one of the radicals L 2a , L 2b is not H;
  • R 1 ' has the meanings given above, preferably the meanings given as being preferred;
  • R 3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen; and
  • R 4b' is CN or a radical R 4b which has the general or preferably preferred meanings given above and is preferably CN or a radical R 4ba .
  • a further particular embodiment of the invention relates to compounds of the formulae 1.8.1 and I.8.2
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 , in particular a radical L 11 or L 12 and specifically L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, preferably H or halogen, where at least one of the radicals L 2a , L 2b is not H;
  • R 1 ' has the meanings given above, preferably the meanings given as being preferred;
  • R 3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen; and
  • R 4c has the general or preferably preferred meanings given above.
  • a further particular embodiment of the invention relates to compounds of the formulae 1.9.1 and I.9.2
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 , in particular a radical L 11 or L 12 and specifically L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, preferably H or halogen, where at least one of the radicals L 2a , L 2b is not H;
  • R 1 ' has the meanings given above, preferably the meanings given as being preferred;
  • R 3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen; and
  • R 4d has the general or preferably preferred meanings given above.
  • a further particular embodiment of the invention relates to compounds of the formulae 1.10.1 and 1.10.2
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 , in particular a radical L 11 or L 12 and specifically L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
  • R 1 ' has the meanings given above, preferably the meanings given as being preferred;
  • R 3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen; and
  • R 4e has the general or preferably preferred meanings given above.
  • Examples of preferred compounds of the general formula I are those of the formulae l.a, l.b, l.c, l.d, l.e and l.f
  • R 4 is 4-bromopyrazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 4-chloropyrazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 4-cyanopyrazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 4-phenylpyrazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 5-methylpyrazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 3,5-dimethylpyrazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • Table 17
  • R 4 is 3-trifluoromethyl-5-methylpyrazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 3,4,5-trimethylpyrazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 1 H-pyrazolin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 3-methyl-1 H-pyrazolin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 3-phenyl-1 H-pyrazolin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 4-methyl-1 H-pyrazolin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is imidazol-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 1-methylimidazol-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 3-trifluoromethyl-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 3-nitro-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 3-methylthio-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 3-bromo-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 3-chloro-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 3,5-dimethyl-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is thiazol-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • Table 40
  • R 4 is thiazol-4-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is isothiazol-3-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is oxazol-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is oxazol-4-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is isoxazol-3-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is [1 ,3,4]-thiadiazol-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is [1 ,2,3]-thiadiazol-4-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 3-chloro-[1 ,2,4]-thiadiazol-5-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • Table 58 Compounds of the formula I. a in which R 3 is chlorine, L 21 is F, L 22 is H, L 1 is -(OCH2)2-OH, R 4 is 4-chloropyridin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • Table 60 Compounds of the formula I. a in which R 3 is chlorine, L 21 is F, L 22 is H, L 1 is -(OCH 2 )2-OH, R 4 is 6-chloropyridin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is pyridazin-3-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 6-methylpyridazin-3-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • Table 63
  • R 4 is 6-chloropyridazin-3-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is pyrimidin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is pyrimidin-4-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 4-chloropyrimidin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 5-chloropyrimidin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 4-methylpyrimidin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 4-methoxypyrimidin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 2-methylpyrimidin-4-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 4,6-dichloro-[1 ,3,5]-triazin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is N-methylbenzimidazol-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is benzoxazol-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is benzothiazol-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is benzothiazol-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 6-nitrobenzothiazol-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is quinolin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • Table 86
  • R 4 is 4-methylquinolin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is isoquinolin-1-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is quinoxalin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 6-chloroquinoxalin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 7-chloroquinoxalin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is 6,7-dichloroquinoxalin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is quinazolin-2-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is quinazolin-4-yl and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • R 4 is -0-N(CHs) 2 and the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • Tables 155 to 308 Compounds of the formula I. a in which the combination of R 3 , R 4 , L 21 and L 22 is as defined in any of Tables 1 to 154, the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A and L 1 is -(OCH2)2-OCH3 instead of -(OCH 2 ) 2 -OH.
  • Tables 771 to 924 Compounds of the formula I. a in which the combination of R 3 , R 4 , L 21 and L 22 is as defined in any of Tables 1 to 154, the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A and L 1 is -(OCH 2 )3-OC 2 H 5 instead of -(OCH 2 ) 2 -OH.
  • Tables 1387 to 1540 Compounds of the formula I. a in which the combination of R 3 , R 4 , L 21 and L 22 is as defined in any of Tables 1 to 154, the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A and L 1 is -0-CH 2 CH 2 -OH instead of -(OCH 2 ) 2 -OH.
  • Tables 2003 to 2156 Compounds of the formula I. a in which the combination of R 3 , R 4 , L 21 and L 22 is as defined in any of Tables 1 to 154, the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A and L 1 is -0-CH 2 CH 2 CH 2 -OCHs instead of -(OCH 2 ) 2 -OH.
  • Tables 2619 to 2772 Compounds of the formula I. a in which the combination of R 3 , R 4 , L 21 and L 22 is as defined in any of Tables 1 to 154, the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A and L 1 is -0-CH 2 CH 2 -N(CHs) 2 instead of -(OCH 2 ) 2 -OH.
  • Tables 3235 to 3388 Compounds of the formula I. a in which the combination of R 3 , R 4 , L 21 and L 22 is as defined in any of Tables 1 to 154, the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A and L 1 is -O-CH2CH2CH2-NHCH3 instead of -(OCH 2 ) 2 -OH.
  • Tables 4005 to 4158 Compounds of the formula I. a in which the combination of R 3 , R 4 , L 21 and L 22 is as defined in any of Tables 1 to 154, the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A and L 1 is -0-CH 2 CH 2 CH 2 CH 2 -NHCHS instead of -(OCH 2 ) 2 -OH.
  • Tables 4159 to 4312 Compounds of the formula I. a in which the combination of R 3 , R 4 , L 21 and L 22 is as defined in any of Tables 1 to 154, the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A and L 1 is -0-CH 2 CH 2 CH 2 CH 2 -NHCHS instead of -(OCH 2 ) 2 -OH.
  • Tables 4159 to 4312 Compounds of the formula I. a in which the combination of R 3 , R 4 , L 21 and L 22 is as defined
  • Tables 6161 to 6314 Compounds of the formula I
  • Tables 12167 to 12320 Tables 12167 to 12320
  • Tables 14169 to 14322 Tables 14169 to 14322
  • Tables 16171 to 16324 Compounds of
  • Tables 18173 to 18326 Tables 18173 to 18326

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Abstract

The present invention relates to novel pyrazine compounds of formula (I), N-oxides or agriculturally useful salts thereof, to their use for controlling harnful fungi, to their use in the treatment of cancer and to fungicidal or pharmaceutical compositions comprising at least one of these compounds as active component.

Description

Pyrazine Compounds
Description
The present invention relates to novel pyrazine compounds, to their use for controlling harmful fungi, to their use in the treatment of cancer and to fungicidal or pharmaceutical compositions comprising at least one of these compounds as active component.
The control of plant diseases caused by phythopathogenic fungi is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumer.
WO 2006/089060 describes pyrazine derivatives which carry in the 2-position an oxygen, sulphur or nitrogen atom bound via a double bond. The 6-position carries an optionally substituted aliphatic, cycloaliphatic, aromatic or heteroaromatic radical and the 3-position a heterocyclic or heteroatom-containing group. The compounds are used for combating harmful fungi.
There is a continuous need for new compounds which are more effective, less costly, less toxic, environmentally safer and/or have different modes of action.
Accordingly, it is an object of the present invention to provide compounds having a better fungicidal activity and/or a better crop plant compatibility.
Moreover, it is an object to provide compounds having an improved pharmacological action.
Surprisingly, these objects are achieved by pyrazine compounds of the general formula I, defined below, and by the N-oxides and the agriculturally acceptable salts of the compounds I.
Accordingly, the present invention relates pyrazine compounds of the formula I, N- oxides or agriculturally useful salts thereof
(I)
Figure imgf000002_0001
where
A is O, S or NR10;
R1 is Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, C3-Cio-cycloalkyl-Ci-C4-alkyl, C3-Cio-cycloalkenyl-Ci-C4-alkyl, a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated non-aromatic carbocyclic ring optionally containing as ring members one or two groups selected from C(=O) and C(=S), phenyl, naphthyl, a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated non-aromatic heterocyclic ring attached via a carbon atom and containing 1 , 2, 3 or 4 heteroatoms selected from O, S and N as ring members and optionally containing as ring members one or two groups selected from C(=O) and C(=S), or a 5- or 6-membered heteroaromatic ring attached via a carbon atom and containing 1 , 2, 3 or 4 heteroatoms selected from O, S and N as ring members; where R1 may be partially or fully halogenated and/or may carry 1 , 2, 3 or 4 identical or different substituents L3;
or R1 is a radical of the formula NR5R6, N=CR7R8 or OR9;
R2 is a carboaromatic or heteroaromatic group selected from phenyl, benzyl, naphthyl, a 5- or 6-membered heteroaromatic radical, where the heteroaromatic radical contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members, and phenyl fused to a saturated or unsaturated aromatic or non-aromatic 5- or 6-membered heterocyclic ring, where the heterocyclic ring contains 1 , 2 or 3 heteroatoms selected from the group consisting of O, S and N as ring members and may furthermore contain 1 or 2 CO groups as ring members, where the carboaromatic or heteroaromatic group carries one substituent L1 and 1 , 2, 3 or 4 identical or different substituents L2;
R3 is hydrogen, halogen, hydroxyl, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-C10- halocycloalkyl, Ci-Cio-alkoxy, Ci-Cio-haloalkoxy , Ci-Cio-alkylthio, C1-C10- haloalkylthio, Ci-Cio-alkylsulfinyl, Ci-Cio-haloalkylsulfinyl, Ci-Cio-alkylsulfonyl, Ci-Cio-haloalkylsulfonyl, Ci-C4-alkoxy-Ci-C4-alkyl, formyl (CHO), Ci-C4- alkylcarbonyl, carboxyl (COOH), Ci-C4-alkoxycarbonyl, SCN, cyano-Ci-C4-alkyl or cyano;
R4 is halogen, cyano, SCN, hydroxyl, mercapto, N3, Ci-C6-alkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, d-Cβ-alkoxy, Cs-Cs-alkenyloxy, Cs-Cs-alkynyloxy, d-Cβ-alkylthio,
Cs-Cs-alkenylthio, Cs-Cs-alkynylthio, C-i-Cβ-alkylsulfinyl, C-i-Cβ-alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, Ci-C6-alkylaminosulfonyl, di-d-Cβ- alkylaminosulfonyl,
C3-Cio-cycloalkyl, phenyl, naphthyl, 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or aromatic heterocyclic ring having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 , 2 or 3 groups selected from C(=O) and C(=S) as ring members, where the heterocyclic ring may be fused to a phenyl ring or to a 5- or 6-membered heteroaromatic ring having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S; or a radical of the formula -ON(=CRaRb), -NRcN=CRaRb, -NRaRb,
-NRcNRaRb, -NRa-CN, -N=ORa; -NRcC(=W)-NRaRb, -NRaC(=W)Rc, -NNRaRbC(=W)-X1-Rc, -ONRaRb,-OC(=W)Rc, -O(C=W)NRaRb, -C(=W)RC, -C(=W)NRaRb, -C(=W)N0Rb, -CRaRb-ORc, -CRaRb-SRc, -CRaRb-NRcRd, -CRaRb-C(=W)Rc, -C(=W)-NRa-X2-Rb, -C(=NX2Ra)-ORb or -C(=NX2Ra)-SRb,
in which
W is O, S, NRd or NNRdRe;
X1 is O or NRf;
X2 is a single bond, -CO-, -CONH-, -COO-, -0-, -NRf-, -CH2-O-CO- or
-CH=CH-(C=O)-, where the left part of the divalent radicals is attached to the nitrogen atom;
Ra, Rb, Rc, Rd, Re, Rf independently of one another are hydrogen, hydroxyl,
C-i-Ce-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, Ci-C6-alkoxy, Ci-C4-alkoxy-Ci-C4- alkyl, Ci-Cβ-alkylcarbonyl, Ci-Cβ-alkoxycarbonyl, Cs-Cβ-cycloalkyl, C3-C6- cycloalkenyl, Cs-Cβ-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, aryl, aryl-Ci- C4-alkyl or a 5- to 10-membered saturated or unsaturated, aromatic or non- aromatic heterocyclic ring having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members;
where, if Ra, Rb, Rc are attached directly to an oxygen atom, they are not hydroxyl, Ci-Cβ-alkoxy or Cs-Cβ-cycloalkoxy;
or Ra and Rb together with the nitrogen atom to which they are attached form a group RC-X11-C(R9)=N in which
Ra is independently defined like Ra or is halogen or cyano; and X11 is independently defined like X1;
or two of the radicals Ra, Rb, Rc, Rd, Re, Rf, Rs together form a C2-C4- alkylene group which may be interrupted by an oxygen atom and/or may contain a C-C double bond,
where the aliphatic, alicyclic, aromatic and/or heterocyclic groups in R4, Ra, Rb, Rc, Rd, Re, Rf and/or Rs may be partially or fully halogenated and/or may carry 1 , 2 or 3 substituents Rx, where
Rx is cyano, SCN, nitro, hydroxyl, mercapto, oxo, C-i-Cβ-alkyl, C-i-Cβ-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6- cycloalkyl, Cs-Cβ-halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6- cycloalkenyl, Ci-Cβ-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyloxy, C3-C6- alkynyloxy, Ci-C6-alkylthio, C-i-Cβ-alkylcarbonyl, carboxyl, Ci-Cβ- alkoxycarbonyl, C-i-Cβ-alkylsulfinyl, C-i-Cβ-alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, Ci-Cβ-alkylaminosulfonyl, di-(Ci-C6-alky)aminosulfonyl, amino, Ci-Cβ-alkylamino, di-(Ci-C6-alkyl)amino, aminocarbonyl, Ci-Cβ- alkylaminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, aminothiocarbonyl, Ci-Cβ-alkylaminothiocarbonyl, di-(Ci-C6-alkyl)aminothiocarbonyl, Ci-Cβ- alkylcarbonylamino, tri-(Ci-C6-alkyl)silyl, aryl, aryloxy, aryl-Ci-C4-alkyl, aryl- Ci-C4-alkoxy, 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclyl, 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclyloxy, 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclylcarbonyl, where the heterocyclyl radicals in the three last-mentioned groups contain 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members, -C(=NORα)-ORβ or -OC(Rα)2-C(Rβ)=NORβ,
where the cyclic radicals in Rx may be unsubstituted or may carry 1 , 2 or 3 radicals Ry, where
Ry is cyano, nitro, halogen, hydroxyl, C-i-Cβ-alkyl, C-i-Cε-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6- cycloalkyl, Cs-Cε-halocycloalkyl, Cs-Cε-cycloalkenyl, C-i-Cβ- alkylsulfonyl, C-i-Cε-alkylsulfinyl, Ci-Cε-alkoxy, Ci-Cε-haloalkoxy, C2-C6-alkenyloxy, Ci-Cε-alkylthio, Ci-Cε-alkoxycarbonyl, amino, Ci-Cε-alkylamino, di-(Ci-C6-alkyl)amino, aminocarbonyl, Ci-Cε- alkylaminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, aminothiocarbonyl, Ci-Cε-alkylaminothiocarbonyl, di-(Ci-C6- alkyl)aminothiocarbonyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclyl, 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclyloxy, where the heterocyclyl radicals in the two last-mentioned groups contain 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members, or
-C(=NORα)-ORβ; where
Rα, Rβ independently of one another are hydrogen or Ci-Cε-alkyl;
R5 is H, Ci-Cio-alkyl, C2-Cio-hydroxyalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, C4-Ci0- alkadienyl, C3-Cio-cycloalkyl, Ci-Cio-alkoxy, C2-Cio-alkenyloxy, C2-Cio-alkynyloxy, amino, d-Cs-alkylamino, di-(Ci-C8-alkyl)amino, phenyl, naphthyl or a saturated or unsaturated aromatic or non-aromatic 5- or 6-membered heterocycle which is attached via a carbon atom, where the heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members and may furthermore contain 1 or 2 CO groups as ring members;
where the aliphatic, alicyclic, aromatic and/or heterocyclic groups in R5 may be partially or fully halogenated and/or may carry 1 , 2, 3 or 4 identical or different substituents Ra1;
R6 is independently defined like R5, or is a group #-CR61R62-(CR63R64)q-(CR65R66)p-Y-Z in which
# is the point of attachment to the nitrogen atom;
R61, R62, R63, R64, R65 and R66 independently of one another are hydrogen, Ci-Cs- alkyl, d-Cs-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, Cs-Cε-cycloalkyl, Cs-Cε-halocycloalkyl, C3-C6- cycloalkenyl, Cs-Cε-halocycloalkenyl, phenyl, naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S; where
R63 with R61 or R66 together with the atoms to which these radicals are attached may also form a five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated ring which, in addition to carbon atoms, may contain one, two or three heteroatoms from the group consisting of O, N and S as ring members and/or may carry one or more substituents Ra1; R61 with R62, R63 with R64, R65 with R66 in each case together may also be oxygen, thus forming carbonyl groups, and form a C2-Cs-alkylene, C2-Cs-alkenylene or C2-C5-alkynylene chain (which may be interrupted by one, two or three heteroatoms from the group consisting of O, N and S), thus forming spiro groups;
R5 and R61 together with atoms to which they are attached may form a 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated heterocycle which, in addition to carbon atoms, may contain one, two or three further heteroatoms from the group consisting of O, N and S as ring members;
where
the aliphatic, alicyclic, heterocyclic, aromatic and/or heteroaromatic radicals in R61 to R66 in each case independently of one another may be partially or fully halogenated and/or may carry one, two, three or four identical or different groups
each Ra1 is independently cyano, nitro, hydroxyl, carboxyl, Ci-Cβ-alkyl, C2-C8- alkenyl, C2-C6-alkynyl, Cs-Cβ-cycloalkyl, C3-C8-cycloalkenyl, d-Cβ-alkoxy,
C2-C6-alkenyloxy, Cs-Cβ-alkynyloxy, Cs-Cβ-cycloalkoxy, C3-C6- cycloalkenyloxy, d-Cβ-alkylthio, amino, Ci-Cβ-alkylamino, di-(Ci-C6- alkyl)amino, C(O)Rπ , C(S)Rπ , C(O)ORπ , C(S)ORπ , C(O)SRπ , C(S)SRπ , C(O)NH2, C(O)NHRπ , C(O)NRπ 2, OC(O)ORπ , OC(O)NH2, OC(O)NHRπ , OC(O)NRn 2, Si(CH3)S, Ci-C6-alkylene, oxy-Ci-C4-alkylene, oxy-Ci-C3- alkyleneoxy, where the three last-mentioned divalent groups may be attached to the same atom or to adjacent atoms, phenyl, naphthyl or a 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S;
each Rπ is independently Ci-C8-alkyl, C3-C8-alkenyl, C3-C8-alkynyl, C3-C6- cycloalkyl or Cs-Cβ-cycloalkenyl;
where the aliphatic, alicyclic, aromatic or heterocyclic groups in the abovementioned groups Ra1 and Rπ for their part may be partially or fully halogenated and/or may carry one, two or three groups Rb1;
each Rb1 is independently cyano, nitro, hydroxyl, mercapto, amino, carboxyl, C-i-Ce-alkyl, C2-C8-alkenyl, d-Ce-alkoxy, C2-C8-alkenyloxy, C2-C8- alkynyloxy, d-Cβ-alkylthio, Ci-Cβ-alkylamino, di-(Ci-C6-alkyl)amino, formyl, Ci-Cβ-alkylcarbonyl, Ci-Cβ-alkylsulfonyl, Ci-Cβ-alkylsulfinyl, Ci-Cβ- alkoxycarbonyl, Ci-Cβ-alkylcarbonyloxy, Ci-Cβ-alkoxycarbonyloxy, aminocarbonyl, aminothiocarbonyl, Ci-Cβ-alkylaminocarbonyl, di-(Ci-C6- alkyl)aminocarbonyl, d-Ce-alkylaminothiocarbonyl, di-(Ci-C6- alkyl)aminothiocarbonyl, C3-Cio-cycloalkyl, C3-Cio-cycloalkoxy, heterocyclyl, heterocyclyloxy, where heterocyclyl in the two lastmentioned radicals is 3- to 10-membered and contains 1 , 2, 3 or 4 heteroatoms selected from the gorup consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members; aryl, aryloxy, arylthio, aryl-Ci-Cβ-alkoxy, aryl-Ci-Cβ-alkyl, hetaryl, hetaryloxy or hetarylthio, where the aryl radicals contain 6 to 10 ring members and the hetaryl radicals 5 or 6 ring members and 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where the alicyclic, heterocyclic, aromatic and/or heteroaromatic systems may be partially or fully halogenated and/or substituted by 1 , 2, 3, 4 or 5 Ci-C4-alkyl and/or Ci-C4-haloalkyl groups;
Y is oxygen or sulfur;
Z is hydrogen, carboxyl, formyl, d-Cs-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, Cs-Ce-cycloalkyl, C3-C8-cycloalkenyl, C(O)Rπ , C(O)ORπ , C(S)ORπ ,
C(O)SRπ , C(S)SRπ , C(NRA)SRπ , C(S)Rπ , C(NRπ )NRARB, C(NRπ )RA, C(NRπ )ORA, C(O)NRARB, C(S)NRARB, Ci-C8-alkylsulfinyl, Ci-C8-alkylthio, d-Cβ-alkylsulfonyl, C(O)-Ci-C4-alkylene-NRAC(NRπ )NRARB, C(S)-CrC4- alkylene-NRAC(NRπ )NRARB, C(NRπ )-Ci-C4-alkylene-NRAC(NRπ )NRARB, phenyl, naphthyl, a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S and which is attached directly or via a carbonyl, thiocarbonyl, Ci-C4-alkylcarbonyl or Ci-C4-alkylthiocarbonyl group; where the carbon chains in group Z may be substituted by one or more groups Rb1;
RA and RB independently of one another are hydrogen, C2-alkenyl, C2-alkynyl or one of the groups mentioned under Rπ ; or
RA and RB together with the nitrogen atom to which they are attached or RA and Rπ together with the carbon atoms and heteroatoms to which they are attached may also form a five- or six-membered saturated, partially unsaturated or aromatic ring which, in addition to carbon atoms, may contain one, two or three further heteroatoms from the group consisting of
O, N and S as ring members and/or may carry one or more substituents Ra1; or
Z with R64 or R66 may also form a five- or six-membered saturated or partially unsaturated ring which, in addition to carbon atoms and Y, may contain one or two further heteroatoms from the group consisting of O, N and S as ring members and/or may carry one or more substituents Ra1;
where the group Z may be partially or fully halogenated and/or carry one, two or three groups Rb1 ;
p is 0, 1 , 2, 3, 4 or 5; and
q is O or i ;
or R5 and R6 together with the nitrogen atom to which they are attached form a saturated or unsaturated aromatic or non-aromatic 5- or 6-membered heterocycle, where the heterocycle may additionally contain 1 , 2 or 3 heteroatoms selected from the group consisting of O, S and N and/or 1 or 2 CO groups as ring members and where the heterocycle may carry 1 , 2 or 3 substituents selected from the group consisting of halogen, hydroxyl, cyano, nitro, carboxyl, Ci-Cs-alkyl, Ci-Cs-haloalkyl, C2-C8-hydroxyalkyl, Ci-Cs-alkoxy, Ci-Cs- haloalkoxy, d-Cs-alkylthio, d-Cs-haloalkylthio, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-Cs-alkynyl, Cs-Cs-haloalkynyl, C2-C8- alkynyloxy, Cs-Cs-haloalkynyloxy, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkoxy, C3-C8- cycloalkenyl, Cs-Cs-cycloalkenyloxy, amino, Ci-Cs-alkylamino, di-(Ci-Cs- alkyl)amino, Ci-Cs-alkylcarbonyl, d-Cs-haloalkylcarbonyl, C2-C8-alkenylcarbonyl, C2-C8-haloalkenylcarbonyl, C2-C8-alkynylcarbonyl, Cs-Cs-haloalkynylcarbonyl, C3-C8-cycloalkylcarbonyl, Cs-Cs-cycloalkenylcarbonyl, d-Cs-alkylcarbonyloxy, d-Cs-haloalkylcarbonyloxy, C2-C8-alkenylcarbonyloxy, C2-C8- haloalkenylcarbonyloxy, C2-C8-alkynylcarbonyloxy, Cs-Cs-haloalkynylcarbonyloxy, Cs-Cs-cycloalkylcarbonyloxy, Cs-Cs-cycloalkenylcarbonyloxy, Ci-Cs- alkoxycarbonyl, Ci-Cs-haloalkoxycarbonyl, C2-C8-alkenyloxycarbonyl, C2-C8- haloalkenyloxycarbonyl, C2-C8-alkynyloxycarbonyl, Cs-Cs-haloalkynyloxycarbonyl, Cs-Cs-cycloalkoxycarbonyl, cycloalkenyloxycarbonyl, aminocarbonyl, Ci-Cs- alkylaminocarbonyl, di-(Ci-C8-alkyl)aminocarbonyl, Ci-Cs-alkoxycarbonyloxy, Ci-Cs-haloalkoxycarbonyloxy, C2-C8-alkenyloxycarbonyloxy, C2-C8- haloalkenyloxycarbonyloxy, C2-C8-alkynyloxycarbonyloxy, C3-C8- haloalkynyloxycarbonyloxy, Cs-Cs-cycloalkoxycarbonyloxy, cycloalkenyloxycarbonyloxy, aminocarbonyloxy, d-Cs-alkylaminocarbonyloxy and di-(Ci-C8-alkyl)aminocarbonyloxy; R7 and R8, independently of each other, are hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl or C3-Cio-cycloalkyl;
or R7 and R8 together with the nitrogen atom to which they are attached form a saturated or unsaturated aromatic or non-aromatic 5- or 6-membered heterocyclic ring, where the heterocyclic ring may additionally contain 1 , 2 or 3 heteroatoms selected from the group consisting of O, S and N and/or 1 or 2 CO groups as ring members and where the heterocyclic ring may carry 1 , 2 or 3 substituents selected from the group consisting of halogen, hydroxyl, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R9 is hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, C3-Cio-cycloalkyl or C3-Cio-cycloalkenyl, where the five last-mentioned radicals may be partially or fully halogenated and/or may carry 1 , 2, 3 or 4 identical or different substituents selected from cyano, SCN, Ci-C4-alkyl, C3-Cio-cycloalkyl, C3-Cio-cycloalkenyl,
Ci-Cβ-alkoxy, C-i-Cβ-thioalkyl, Ci-Cβ-alkylcarbonyl, Ci-Cβ-alkoxycarbonyl, C-i-Cβ- alkylamino, di-(Ci-C6-alkyl)-amino, tri-(Ci-C4-alkyl)-silyl and a group #-CR61R62- (CR63R64)q-(CR65R66)p-Y-Z, where #, R61, R62, R63, R64, R65, R66, Y, Z, q and p are as defined above;
R10 is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, Ci-Cio-alkylcarbonyl or C1-C10- alkoxycarbonyl;
L1 is a group of the formula -Y1-Y2-T, -C(RV)=C(RW)-Y1-Y2-T or -C≡C-Y1-Y2-T in which
Y1 is CRhR', C(=T2)O, C(=T2)NRh, OC(=T2), O, NRh or S(O)r; Y2 is d-Cs-alkylene, C2-Cs-alkenylene or C2-C8-alkynylene, where Y2 may be interrupted by one, two, three or four heteroatoms from the group consisting of NRh, O and S(O)r; r is O, 1 or 2;
T is V1Rh, V1RZ, NRhR', V1NRhR', C(O)ORh, C(O)NRhR', S(O)rRh, C(NORh)R', NRh-T1-C(=T2)-T3, T1-C(=T2)-[(Y2)b-C(=T2)]c-T3, T1-C(=T2)-[Y2-T1-C(=T2)]c-T3, T1-C(=T2)-[T1-Y2-C(=T2)]c-T3 or T1-C(=T2)-[NRh-(NR')b-C(=T2)]c-T3, in which T1 is a direct bond, O, S or NRh; T2 is O, S or NRh;
T3 is Rh, Rz, ORh, SRh or NRhR'; V1 is O or S; b is O or i ; c is 0, 1 , 2, 3, 4 or 5; Rz is NR5R6 or Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-halo- alkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Ci2-cycloalkenyl, C3- Ci2-halocycloalkenyl, phenyl, halophenyl, naphthyl, halonaphthyl or a 5-, 6-, 7-, 8-, 9-, or 10-membered saturated, partially unsaturated or aromatic heterocyclic ring which is attached via carbon, which may be partially or fully halogenated and contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur; where Rz may contain 1 , 2, 3 or 4 identical or different groups Ra1, where R5, R6 and Ra1 are as defined above; each Rh and each R1, independently of each other, are hydrogen, Ci-Cs-alkyl, C2- Cs-alkenyl, C2-C8-alkynyl, Cs-Cβ-cycloalkyl or Cs-Cβ-cycloalkenyl, phenyl, naphthyl, a 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or aromatic heterocyclic ring which contains 1 , 2, 3 or 4 heteroatoms from the group consisting of O, N and S, where the groups Rh and R1 may be partially or fully halogenated and where the aliphatic, alicyclic, aromatic or heterocyclic groups in the above- mentioned groups Rh and R1 for their part may carry one, two or three groups Rb1, where Rb1 is as defined above;
Rv and Rw, independently of each other, are hydrogen, halogen, hydroxy, CN, nitro, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkinyl, Ci-Cio-haloalkyl, C2-C10- haloalkenyl, C2-Cio-haloalkinyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, C3- Cio-cycloalkenyl, C3-Cio-halocycloalkenyl, ORD, S(O)rRD, NRDRE, CO-RE, COORE, CONRDRE, CRD(=N)ORE; phenyl, napthyl, an aromatic heterocyclic ring which is attached via a carbon atom and which may be partially or fully halogenated and contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which aromatic groups may be substituted by 1 to 5 radicals RF; where RF is halogen, hydroxy, CN, nitro, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-C10- alkinyl, Ci-Cio-haloalkyl, C2-Cio-haloalkenyl, C2-Cio-haloalkinyl, C3- Cio-cycloalkyl, C3-Cio-halocycloalkyl, C3-Cio-cycloalkenyl, C3-C10- halocycloalkenyl, Ci-Cβ-alkoxy, Ci-Cβ-haloalkoxy, C-i-Cβ-alkylthio, Ci- Cβ-haloalkylthio, Ci-Cβ-alkylsulfinyl, Ci-Cβ-haloalkylsulfinyl, Ci-Cβ- alkylsulfonyl, Ci-Cβ-haloalkylsulfonyl, (Ci-C6-alkoxy)carbonyl, (C-i-Cβ- haloalkoxy)carbonyl, NRGRH, CORGRH, CO-NRGRH or CRG(=N)ORH, wherein RG and RH are, independently of one another, Ci-Cβ-alkyl or C-i-Cβ- haloalkyl; RD,RE, independently of each other, are hydrogen, halogen, hydroxy, Ci-
Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkinyl, Ci-Cio-haloalkyl, C2-C10- haloalkenyl, C2-Cio-haloalkinyl, C3-Cio-cycloalkyl, C3-C10- halocycloalkyl, C3-Cio-cycloalkenyl, C3-Cio-halocycloalkenyl, or unsubstituted or substituted phenyl, napthyl or an aromatic heterocyclic ring which is as defined in Rv; each L2 is independently halogen, hydroxyl, mercapto (SH), cyano, cyanato (OCN), nitro, carboxyl (COOH), Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-hydroxyalkyl, Ci-Cio-alkoxy, Ci-do-haloalkoxy, Ci-Cio-alkylthio, Ci-Cio-haloalkylthio, C2-C10- alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkenyloxy, C2-Cio-alkynyl, C3-Cio-haloalkynyl, C2-Cio-alkynyloxy, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, C3-Cio-cycloalkoxy, C3-Cio-cycloalkyl-Ci-C4-alkyl, C3-Cio-cycloalkenyl, Ci-Cio-alkoxycarbonyl, C1-C10- haloalkoxycarbonyl, C2-Cio-alkenyloxycarbonyl, C2-Cio-alkynyloxycarbonyl,
Ci-Cio-alkylcarbonyloxy, Ci-do-alkenylcarbonyloxy, Ci-Cio-alkynylcarbonyloxy, aminocarbonyl, Ci-C-io-alkylaminocarbonyl, di-(Ci-Cio-alkyl)aminocarbonyl, Ci-Cio-alkoximinoalkyl, C2-Cio-alkenyloximinoalkyl, C2-Cio-alkynyloximinoalkyl, formyl, Ci-do-alkylcarbonyl, C2-Cio-alkenylcarbonyl, C2-Cio-alkynylcarbonyl, Cs-Ce-cycloalkylcarbonyl, NRjRk, NRJ-(C=O)-Rk, S(=O)nA1, C(=S)A2, a group
-C(=N-OR')(NRmRn), a group -C(=N-NR°Rp)(NRqRr) or tri-(Ci-d)alkylsilyl;
in which
RJ, Rk, R1, Rm, Rn, R0, RP, R^, Rr are each independently H, d-C8-alkyl, CrC8- haloalkyl, C2-C8-hydroxyalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8- alkynyl, Cs-Cs-cycloalkyl or Cs-Cs-cycloalkenyl; or
Rm and Rn, R0 and RP and/or R? and Rr together with the nitrogen atom to which they are attached form a four-, five- or six-membered saturated or partially unsaturated ring which may carry one, two, three or four substituents independently of one another selected from L5;
A1 is hydrogen, hydroxyl, d-Cs-alkyl, amino, d-Cs-alkylamino or di-(Ci-C8- alkyl)amino;
A2 is C2-C8-alkenyl, d-Cs-alkoxy, Ci-Cβ-haloalkoxy, C2-Cio-alkenyloxy, C2-C10- alkynyloxy or one of the groups mentioned under A1; and
n is O, 1 or 2;
each L3 is independently halogen, hydroxyl, mercapto (SH), cyano, cyanato (OCN), nitro, carboxyl (COOH), Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-hydroxyalkyl, Ci-Cio-alkoxy, Ci-Cio-haloalkoxy, Ci-Cio-alkylthio, C2-Cio-alkenyl, C2-C10- haloalkenyl, C2-Cio-alkenyloxy, C2-Cio-alkynyl, C3-Cio-cycloalkyl, C3-C10- cycloalkoxy,
Figure imgf000012_0001
C3-Cio-cycloalkenyl, C1-C10- alkoxycarbonyl, Ci-Cio-haloalkoxycarbonyl, C2-Cio-alkenyloxycarbonyl, C1-C10- alkylcarbonyloxy, Ci-do-alkenylcarbonyloxy, aminocarbonyl, C1-C10- alkylaminocarbonyl, di-(Ci-Cio-alkyl)aminocarbonyl, Ci-Cio-alkoximinoalkyl, C2-Cio-alkenyloximinoalkyl, formyl, Ci-Cio-alkylcarbonyl, C2-Cio-alkenylcarbonyl,
Cs-Ce-cycloalkylcarbonyl, NRRk, NRJ-(C=O)-Rk, S(=O)nA1, C(=S)A2, a group - C(=N-OR')(NRmRn), a group -C(=N-NR°Rp)(NRqRr) or tri-(Ci-C4)alkylsilyl, where RJ, Rk, R1, Rm, Rn, R0, RP, Ri, Rr, A1, A2 and n are as defined above;
or is a group #-(CR61R62)Pi-(CR63R64)q-(CR65R66)P-Y-Z, where #, R61, R62, R63, R64, R65, R66, Y, Z, q and p are as defined above and p1 is 0 or 1 ;
or is phenyl, naphthyl or a saturated or unsaturated aromatic or non-aromatic 5-, 6-, 7-, 8-, 9- or 10-membered heterocyclic ring, where the heterocyclic ring contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members and may furthermore contain one or two CO groups as ring members, where the aliphatic, alicyclic, aromatic and heterocyclic groups in L3 for their part may be partially or fully halogenated and/or may carry 1 , 2 or 3 substituents L4;
each L4 is independently cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Ci-Cβ-alkyl, d-Cβ-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, C4-C8-alkadienyl, C2-C8- alkenyloxy, C2-C8-alkynyloxy, d-Cβ-alkoxy, d-Cβ-haloalkoxy, d-Cβ-alkylthio, Ci-Cβ-alkylamino, di-(Ci-C6-alkyl)amino, C3-C8-cycloalkylamino, (Ci-C6-alkyl)(C3- C8-cycloalkyl)amino, formyl, d-Cβ-alkylcarbonyl, d-Cβ-alkylsulfonyl, C-i-Cβ- alkylsulfinyl, C-i-Cβ-alkoxycarbonyl, d-Cβ-alkylcarbonyloxy, C-i-Cβ- alkylaminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, Ci-Cβ-alkylaminothiocarbonyl, di-(Ci-C6-alkyl)aminothiocarbonyl, tri-(Ci-C4-alkyl)silyl, C3-C8-cycloalkyl, C3-C8- halocycloalkyl, bicycloalkyl, C3-C8-cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, arylthio, aryl-Ci-Cβ-alkoxy or aryl-Ci-C6-alkyl, where the heterocyclyl radicals may be saturated or unsaturated, aromatic or non-aromatic and have 5 to 10 ring members and 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N and optionally one or two carbonyl groups as ring members and where the cyclic systems may be partially or fully halogenated and/or substituted by Ci-C6-alkyl or d-Cβ-haloalkyl groups; and
each L5 is in each case independently selected from the group consisting of hydroxyl, cyano, nitro, Ci-C8-alkyl, Ci-C8-haloalkyl, C2-C8-hydroxyalkyl, Ci-C8-alkoxy, Ci-C8-haloalkoxy, Ci-C8-alkylthio, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8- alkenyloxy, C2-C8-alkynyl, C2-C8-alkynyloxy, C3-C8-cycloalkyl, amino, Ci-C8- alkylamino and di-(Ci-C8-alkyl)amino.
The present invention also provides the use of pyrazine compounds of the formula I, their N-oxides and/or their agriculturally useful salts for controlling harmful fungi. Moreover, the invention provides the use of the pyrazine compounds I, their N-oxides and/or their pharmaceutically acceptable salts for preparing a medicament for the treatment of cancer.
The invention further provides fungicidal or pharmaceutical compositions comprising these compounds I, their N-oxides and/or their agriculturally or pharmaceutically acceptable salts and suitable carriers. Suitable agriculturally and/or pharmaceutically acceptable carriers are described below.
The compounds I can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, e.g. a racemate, individual stereoisomers, or as an optically active form.
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 I. Thus, 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, preferably tri(Ci-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate 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.
Suitable pharmaceutically acceptable salts are especially physiologically tolerated salts of the compound I, in particular the acid addition salts with physiologically acceptable acids. Examples of suitable organic and inorganic acids are hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, Ci-C4-alkylsulfonic acids, such as methanesulfonic acid, aromatic sulfonic acids, such as benzenesulfonic acid and toluenesulfonic acid, oxalic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, adipic acid and benzoic acid. Further suitable acids are described, for example, in Fortschritte der Arzneimittelforschung, Volume 10, pages 224 ff., Birkhauser Verlag, Basle and Stuttgart, 1966, the entire contents of which is expressly incorporated herein by way of reference.
In the definitions of the variables given in the formulae above, collective terms are used which are generally representative for the substituents in question. The term Cn-Cm indicates the number of carbon atoms possible in each case in the substituent or substitutent moiety in question:
Halogen: fluorine, chlorine, bromine and iodine;
Alkyl and the alkyl moieities in alkoxy, alkylcarbonyl, alkylthiocarbonyl, alkylcarbonyloxy, alkylthiocarbonyloxy, alkylamino, dialkylamino, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylaminothiocarbonyloxy, dialkylaminothiocarbonyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl and the like: saturated straight-chain or branched hydrocarbon radicals having 1 to 2, 1 to 4, 1 to 6, 1 to 8 or 1 to 10 carbon atoms. Ci-C2-Alkyl is methyl or ethyl. CrC4-AIkVl is additionally also, for example, propyl, isopropyl, butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1 ,1-dimethylethyl (tert-butyl). Ci-Cβ-Alkyl is additionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 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-methylpropyl, or 1 -ethyl-2- methylpropyl. d-Cs-Alkyl is additionally also, for example, heptyl, octyl, 2-ethylhexyl and positional isomers thereof. Ci-Cio-Alkyl is additionally also, for example, nonyl, decyl and positional isomers thereof.
Branched Cs-Cs-alkyl: is an alkyl group having 3 to 8 carbon atoms, at least one of which is a secondary or tertiary carbon atom. Examples are isopropyl, tert-butyl, 2-butyl, isobutyl (2-methylpropyl), 2-pentyl, 2-methylbutyl, 2-hexyl, 3-methylpentyl, 1 ,1- dimethylbutyl, 1 ,2-dimethylbutyl, 1-methyl-1-ethylpropyl and the like.
Haloalkyl: straight-chain or branched alkyl groups having 1 to 2, 1 to 4, 1 to 6, 1 to 8 or 1 to 10 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above: in particular Ci-C2-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 or 1 ,1 ,1-trifluoroprop-2- yi;
Ci-Cio-Hydroxyalkyl: straight-chain or branched alkyl groups having 1 to 2, 1 to 4, 2 to 4, 1 to 6, 2 to 6, 1 to 8, 2 to 8, 1 to 10 or 2 to 10 carbon atoms (as mentioned above), where at least one of the hydrogen atoms is replaced by a hydroxyl group, such as in 2-hydroxyethyl or 3-hydroxypropyl.
Alkenyl and the alkenyl moieties in alkenyloxy, alkenylcarbonyl and the like: monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6, 2 to 8, 3 to 8, 2 to 10 or 3 to 10 carbon atoms and a double bond in any position, for example C2-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, 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-3-pentenyl, 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-1- methyl-2-propenyl, 1-ethyl-2-methyl-1 -propenyl, 1-ethyl-2-methyl-2-propenyl and the like;
Alkadienyl: doubly unsaturated straight-chain or branched hydrocarbon radicals having 4 to 6, 4 to 8 or 4 to 10 carbon atoms and two double bonds in any position, but preferably not cumulated, for example 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, hepta-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-dienyl and the like;
Haloalkenyl and the haloalkenyl moieties in haloalkenyloxy, haloalkenylcarbonyl and the like: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and a double bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like;
Alkynyl and the alkynyl moieties in alkynyloxy, alkynylcarbonyl and the like: straight- chain or branched hydrocarbon groups having 2 to 4, 2 to 6, 2 to 8, 3 to 8, 2 to 10 or 3 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-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, 1-ethyl-1-methyl-2-propynyl and the like;
Haloalkynyl and the haloalkynyl moieties in haloalkynyloxy, haloalkynylcarbonyl and the like: unsaturated straight-chain or branched hydrocarbon radicals having 3 to 4, 3 to 6, 3 to 8 or 3 to 10 carbon atoms and one or two triple bonds in any position (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;
Cycloalkyl and the cycloalkyl moieties in cycloalkoxy, cycloalkylcarbonyl and the like; monocyclic saturated hydrocarbon groups having 3 to 6, 3 to 8 or 3 to 10 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl;
Halocycloalkyl and the halocycloalkyl moieties in halocycloalkoxy, halocycloalkylcarbonyl and the like: monocyclic saturated hydrocarbon groups having 3 to 6, 3 to 8 or 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;
Figure imgf000018_0001
Ci-C4-alkyl (as defined above) where one hydrogen atom is replaced by a cycloalkyl group, for example cyclopropyl methyl, cyclopentylmethyl, cyclohexylmethyl and the like.
Cycloalkenyl: monocyclic monounsaturated hydrocarbon groups having 3 to 10, 3 to 8, 3 to 6, preferably 5 to 6, carbon ring members, such as cyclopenten-1-yl, cyclopenten- 3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl and the like;
Halocycloalkenyl: monocyclic monounsaturated hydrocarbon groups having 3 to 10, 3 to 8, 3 to 6, preferably 5 to 6, 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;
bicycloalkyl: a bicyclic hydrocarbon radical having 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, bicyclo[4.4.0]decyl, decalin and the like;
Alkoxy: an alkyl group attached via oxygen. Ci-C2-Alkoxy is methoxy or ethoxy. C1-C4- Alkoxy is additionally, for example, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1-dimethylethoxy (tert- butoxy). Ci-Cβ-Alkoxy is additionally, for example, 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 or 1-ethyl-2-methylpropoxy. Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof. Ci-Cio-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.
Haloalkoxy: an alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine. Ci-C2-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, 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 or OC2Fs Ci-C4-Haloalkoxy is additionally, for example, 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, OCH2-C2F5, OCF2- C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2CI)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. Ci-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
Alkenyloxy: alkenyl as mentioned above which is attached via an oxygen atom, for example Cs-Cβ-alkenyloxy, such as 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy, 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-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 -butenyloxy, 2-ethyl-2-butenyloxy, 2-ethyl-3-butenyloxy, 1 ,1 ,2-trimethyl-2-propenyloxy, 1 -ethyl-1 - methyl-2-propenyloxy, 1-ethyl-2-methyl-1 -propenyloxy and 1-ethyl-2-methyl-2- propenyloxy;
Haloalkenyloxy: an alkenyloxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
Alkynyloxy: alkynyl as mentioned above which is attached via an oxygen atom, for example Cs-Cβ-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;
Haloalkynyloxy: an alkynyloxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine. Cycloalkoxy: cycloalkoxy as mentioned above which is attached via an oxygen atom, for example C3-Cio-cycloalkoxy or Cs-Cs-cycloalkoxy, such as cyclopropoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy and the like;
Cycloalkenyloxy: cycloalkenyloxy as mentioned above which is attached via an oxygen atom, for example C3-Cio-cycloalkenyloxy, Cs-Cs-cycloalkenyloxy or, preferably, Cs-Cβ- cycloalkenyloxy, such as cyclopent-1-enoxy, cyclopent-2-enoxy, cyclohex-1-enoxy and cyclohex-2-enoxy;
Alkoxyalkyl: alkyl as defined above having 1 to 8, 1 to 6 or 1 to 4, in particular 1 to 3, carbon atoms, in which one hydrogen atom is replaced by an alkoxy group having 1 to 8, 1 to 6 or 1 to 4 carbon atoms, for example methoxymethyl, 2-methoxyethyl, ethoxymethyl, 3-methoxypropyl, 3-ethoxypropyl and the like.
Cyanoalkyl: alkyl as defined above having 1 to 8, 1 to 6 or 1 to 4, in particular 1 to 3, carbon atoms in which one hydrogen atom is replaced by a cyano group;
Alkylcarbonyl: group of the formula R-CO- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-C8-alkyl, d-Ce-alkyl, Ci-C4-alkyl or Ci-C2-alkyl. Examples are acetyl, propionyl and the like.
Alkylthiocarbonyl: group of the formula R-CS- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs-alkyl, C-i-Cβ-alkyl, Ci-C4-alkyl or Ci-C2-alkyl. Examples are thioacetyl, thiopropionyl and the like.
Haloalkylcarbonyl: group of the formula R-CO- in which R is a haloalkyl group as defined above, for example Ci-Cio-haloalkyl, Ci-Cs-haloalkyl, C-i-Cβ-haloalkyl, C1-C4- haloalkyl or Ci-C2-haloalkyl. Examples are trifluoroacetyl, trifluoropropionyl and the like.
Haloalkylthiocarbonyl: group of the formula R-CS- in which R is a haloalkyl group as defined above, for example Ci-Cio-haloalkyl, Ci-Cs-haloalkyl, d-Cβ-haloalkyl, C1-C4- haloalkyl or Ci-C2-haloalkyl. Examples are trifluorothioacetyl, trifluorothiopropionyl and the like.
Alkenylcarbonyl: group of the formula R-CO- in which R is an alkenyl group as defined above, for example C2-Cio-alkenyl, C2-Cs-alkenyl, C2-C6-alkenyl or C2-C4-alkenyl.
Alkenylthiocarbonyl: group of the formula R-CS- in which R is an alkenyl group as defined above, for example C2-Cio-alkenyl, C2-Cs-alkenyl, C2-C6-alkenyl or C2-C4- alkenyl. Haloalkenylcarbonyl: group of the formula R-CO- in which R is a haloalkenyl group as defined above, for example C2-Cio-haloalkenyl, C2-C8-haloalkenyl, C2-C6-haloalkenyl or C2-C4-haloalkenyl.
Haloalkenylthiocarbonyl: group of the formula R-CS- in which R is a haloalkenyl group as defined above, for example C2-Cio-haloalkenyl, C2-C8-haloalkenyl, C2-C6-haloalkenyl or C2-C4-haloalkenyl.
Alkynylcarbonyl: group of the formula R-CO- in which R is an alkynyl group as defined above, for example C2-Cio-alkynyl, C2-C8-alkynyl, C2-C6-alkynyl or C2-C4-alkynyl.
Alkynylthiocarbonyl: group of the formula R-CS- in which R is an alkynyl group as defined above, for example C2-Cio-alkynyl, C2-C8-alkynyl, C2-C6-alkynyl or C2-C4- alkynyl.
Haloalkynylcarbonyl: group of the formula R-CO- in which R is a haloalkynyl group as defined above, for example C2-Cio-haloalkynyl, C2-Cs-haloalkynyl, C2-C6-haloalkynyl or C2-C4-haloalkynyl.
Haloalkynylthiocarbonyl: group of the formula R-CS- in which R is a haloalkynyl group as defined above, for example C2-Cio-haloalkynyl, C2-C8-haloalkynyl, C2-C6-haloalkynyl or C2-C4-haloalkynyl.
Cycloalkylcarbonyl: group of the formula R-CO- in which R is a cycloalkyl group as defined above, for example C3-Cio-cycloalkyl, Cs-Cs-cycloalkyl, Cs-Cβ-cycloalkyl or C5-C6-cycloalkyl.
Cycloalkylthiocarbonyl: group of the formula R-CS- in which R is a cycloalkyl group as defined above, for example C3-Cio-cycloalkyl, Cs-Cs-cycloalkyl, Cs-Cβ-cycloalkyl or Cs-Ce-cycloalkyl.
Cycloalkenylcarbonyl: group of the formula R-CO- in which R is a cycloalkenyl group as defined above, for example C3-Cio-cycloalkenyl, Cs-Cs-cycloalkenyl, Cs-Cβ-cycloalkenyl or C5-C6-cycloalkenyl.
Cycloalkenylthiocarbonyl: group of the formula R-CS- in which R is a cycloalkenyl group as defined above, for example C3-Cio-cycloalkenyl, Cs-Cs-cycloalkenyl, C3-C6- cycloalkenyl or Cs-Cβ-cycloalkenyl.
Alkylcarbonyloxy: group of the formula R-CO-O- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, C-i-Cs-alkyl, Ci-Cβ-alkyl, Ci-C4-alkyl or Ci-C2-alkyl. Examples are acetyloxy, propionyloxy and the like. Alkylthiocarbonyloxy: group of the formula R-CS-O- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, C-i-Cs-alkyl, Ci-Cβ-alkyl, Ci-C4-alkyl or C1-C2- alkyl. Examples are thioacetyloxy, thiopropionyloxy and the like.
Haloalkylcarbonyloxy: group of the formula R-CO-O- in which R is a haloalkyl group as defined above, for example Ci-Cio-haloalkyl, Ci-Cs-haloalkyl, C-i-Cβ-haloalkyl, C1-C4- haloalkyl or Ci-C2-haloalkyl. Examples are trifluoracetyloxy, trifluropropionyloxy and the like.
Haloalkylthiocarbonyloxy: group of the formula R-CS-O- in which R is a haloalkyl group as defined above, for example Ci-Cio-haloalkyl, Ci-Cs-haloalkyl, C-i-Cβ-haloalkyl, C1-C4- haloalkyl or Ci-C2-haloalkyl. Examples are trifluorothioacetyloxy, trifluorothiopropionyloxy and the like.
Alkenylcarbonyloxy: group of the formula R-CO-O- in which R is an alkenyl group as defined above, for example C2-Cio-alkenyl, C2-C8-alkenyl, C2-C6-alkenyl or C2-C4- alkenyl.
Alkenylthiocarbonyloxy: group of the formula R-CS-O- in which R is an alkenyl group as defined above, for example C2-Cio-alkenyl, C2-C8-alkenyl, C2-C6-alkenyl or C2-C4- alkenyl.
Haloalkenylcarbonyloxy: group of the formula R-CO-O- in which R is a haloalkenyl group as defined above, for example C2-Cio-haloalkenyl, C2-C8-haloalkenyl, C2-C6- haloalkenyl or C2-C4-haloalkenyl.
Haloalkenylthiocarbonyloxy: group of the formula R-CS-O- in which R is a haloalkenyl group as defined above, for example C2-Cio-haloalkenyl, C2-C8-haloalkenyl, C2-C6- haloalkenyl or C2-C4-haloalkenyl.
Alkynylcarbonyloxy: group of the formula R-CO-O- in which R is an alkynyl group as defined above, for example C2-Cio-alkynyl, C2-Cs-alkynyl, C2-C6-alkynyl or C2-C4- alkynyl.
Alkynylthiocarbonyloxy: group of the formula R-CS-O- in which R is an alkynyl group as defined above, for example C2-Cio-alkynyl, C2-C8-alkynyl, C2-C6-alkynyl or C2-C4- alkynyl.
Haloalkynylcarbonyloxy: group of the formula R-CO-O- in which R is a haloalkynyl group as defined above, for example C2-Cio-haloalkynyl, C2-Cs-haloalkynyl, C2-C6- haloalkynyl or C2-C4-haloalkynyl. Haloalkynylthiocarbonyloxy: group of the formula R-CS-O- in which R is a haloalkynyl group as defined above, for example C2-Cio-haloalkynyl, C2-C8-haloalkynyl, C2-C6- haloalkynyl or C2-C4-haloalkynyl.
Cycloalkylcarbonyloxy: group of the formula R-CO-O- in which R is a cycloalkyl group as defined above, for example C3-Cio-cycloalkyl, Cs-Cs-cycloalkyl, Cs-Cβ-cycloalkyl or C5-C6-cycloalkyl.
Cycloalkylthiocarbonyloxy: group of the formula R-CS-O- in which R is a cycloalkyl group as defined above, for example C3-Cio-cycloalkyl, Cs-Cs-cycloalkyl, C3-C6- cycloalkyl or Cs-Cβ-cycloalkyl.
Cycloalkenylcarbonyloxy: group of the formula R-CO-O- in which R is a cycloalkenyl group as defined above, for example C3-Cio-cycloalkenyl, Cs-Cs-cycloalkenyl, C3-C6- cycloalkenyl or Cs-Cβ-cycloalkenyl.
Cycloalkenylthiocarbonyloxy: group of the formula R-CS-O- in which R is a cycloalkenyl group as defined above, for example C3-Cio-cycloalkenyl, Cs-Cs-cycloalkenyl, C3-C6- cycloalkenyl or Cs-Cβ-cycloalkenyl.
Alkoxycarbonyl: group of the formula R-CO- in which R is an alkoxy group as defined above, for example Ci-Cio-alkoxy, Ci-Cs-alkoxy, Ci-C6-alkoxy, Ci-C4-alkoxy or C1-C2- alkoxy. Examples are methoxycarbonyl, ethoxycarbonyl and the like.
Alkoxythiocarbonyl: group of the formula R-CS- in which R is an alkoxy group as defined above, for example Ci-Cio-alkoxy, Ci-Cs-alkoxy, Ci-C6-alkoxy, Ci-C4-alkoxy or Ci-C2-alkoxy. Examples are methoxythiocarbonyl, ethoxythiocarbonyl and the like.
Haloalkoxycarbonyl: group of the formula R-CO- in which R is a haloalkoxy group as defined above, for example Ci-Cio-haloalkoxy, Ci-Cs-haloalkoxy, Ci-C6-haloalkoxy, Ci-C4-haloalkoxy or Ci-C2-haloalkoxy. Examples are trifluoromethoxycarbonyl, trifluoroethoxycarbonyl and the like.
Haloalkoxythiocarbonyl: group of the formula R-CS- in which R is a haloalkoxy group as defined above, for example Ci-Cio-haloalkoxy, Ci-Cs-haloalkoxy, Ci-C6-haloalkoxy, Ci-C4-haloalkoxy or Ci-C2-haloalkoxy. Examples are trifluoromethoxythiocarbonyl, trifluoroethoxythiocarbonyl and the like.
Alkenyloxycarbonyl: group of the formula R-CO- in which R is an alkenyloxy group as defined above, for example C2-Cio-alkenyloxy, C2-Cs-alkenyloxy, C2-C6-alkenyloxy or C2-C4-alkenyloxy. Alkenyloxythiocarbonyl: group of the formula R-CS- in which R is an alkenyloxy group as defined above, for example C2-Cio-alkenyloxy, C2-C8-alkenyloxy, C2-C6-alkenyloxy or C2-C4-alkenyloxy.
Haloalkenyloxycarbonyl: group of the formula R-CO- in which R is a haloalkenyloxy group as defined above, for example C2-Cio-haloalkenyloxy, C2-C8-haloalkenyloxy, C2-C6-haloalkenyloxy or C2-C4-haloalkenyloxy.
Haloalkenyloxythiocarbonyl: group of the formula R-CS- in which R is a haloalkenyloxy group as defined above, for example C2-Cio-haloalkenyloxy, C2-C8-haloalkenyloxy, C2-C6-haloalkenyloxy or C2-C4-haloalkenyloxy.
Alkynyloxycarbonyl: group of the formula R-CO- in which R is an alkynyloxy group as defined above, for example C2-Cio-alkynyloxy, C2-C8-alkynyloxy, C2-C6-alkynyloxy or C2-C4-alkynyloxy.
Alkynyloxythiocarbonyl: group of the formula R-CS- in which R is an alkynyloxy group as defined above, for example C2-Cio-alkynyloxy, C2-Cs-alkynyloxy, C2-C6-alkynyloxy or C2-C4-alkynyloxy.
Haloalkynyloxycarbonyl: group of the formula R-CO- in which R is a haloalkynyloxy group as defined above, for example C2-Cio-haloalkynyloxy, C2-C8-haloalkynyloxy, C2-C6-haloalkynyl or C2-C4-haloalkynyloxy.
Haloalkynyloxythiocarbonyl: group of the formula R-CS- in which R is a haloalkynyloxy group as defined above, for example C2-Cio-haloalkynyloxy, C2-C8-haloalkynyloxy, C2-C6-haloalkynyl or C2-C4-haloalkynyloxy.
Cycloalkyloxycarbonyl: group of the formula R-CO- in which R is a cycloalkyloxy group as defined above, for example C3-Cio-cycloalkyloxy, Cs-Cs-cycloalkyloxy, C3-C6- cycloalkyloxy or Cs-Cβ-cycloalkyloxy.
Cycloalkyloxythiocarbonyl: group of the formula R-CS- in which R is a cycloalkyloxy group as defined above, for example C3-Cio-cycloalkyloxy, Cs-Cs-cycloalkyloxy, C3-C6- cycloalkyloxy or Cs-Cβ-cycloalkyloxy.
Cycloalkenyloxycarbonyl: group of the formula R-CO- in which R is a cycloalkenyloxy group as defined above, for example C3-Cio-cycloalkenyloxy, Cs-Cs-cycloalkenyloxy, C3-C6-cycloalkenyloxy or Cs-Cβ-cycloalkenyloxy. Cycloalkenyloxythiocarbonyl: group of the formula R-CS- in which R is a cycloalkenyloxy group as defined above, for example C3-Cio-cycloalkenyloxy, C3-C8- cycloalkenyloxy, Cs-Cβ-cycloalkenyloxy or Cs-Cβ-cycloalkenyloxy.
Alkoxycarbonyloxy: group of the formula R-CO-O- in which R is an alkoxy group as defined above, for example Ci-Cio-alkoxy, Ci-Cs-alkoxy, Ci-Cβ-alkoxy, Ci-C4-alkoxy or Ci-C2-alkoxy. Examples are methoxycarbonyl, ethoxycarbonyl and the like.
Alkoxythiocarbonyloxy: group of the formula R-CS-O- in which R is an alkoxy group as defined above, for example Ci-Cio-alkoxy, Ci-Cs-alkoxy, Ci-Cβ-alkoxy, Ci-C4-alkoxy or Ci-C2-alkoxy. Examples are methoxycarbonyl, ethoxycarbonyl and the like.
Haloalkoxycarbonyloxy: group of the formula R-CO-O- in which R is a haloalkoxy group as defined above, for example Ci-Cio-haloalkoxy, Ci-Cs-haloalkoxy, Ci-C6-haloalkoxy, Ci-C4-haloalkoxy or Ci-C2-haloalkoxy. Examples are trifluoromethoxycarbonyl, trifluoroethoxycarbonyl and the like.
Haloalkoxythiocarbonyloxy: group of the formula R-CS-O- in which R is a haloalkoxy group as defined above, for example Ci-Cio-haloalkoxy, Ci-Cs-haloalkoxy, C-i-Cβ- haloalkoxy, Ci-C4-haloalkoxy or Ci-C2-haloalkoxy. Examples are trifluoromethoxycarbonyl, trifluoroethoxycarbonyl and the like.
Alkenyloxycarbonyloxy: group of the formula R-CO-O- in which R is an alkenyloxy group as defined above, for example C2-Cio-alkenyloxy, C2-C8-alkenyloxy, C2-C6- alkenyloxy or C2-C4-alkenyloxy.
Alkenyloxythiocarbonyloxy: group of the formula R-CS-O- in which R is an alkenyloxy group as defined above, for example C2-Cio-alkenyloxy, C2-C8-alkenyloxy, C2-C6- alkenyloxy or C2-C4-alkenyloxy.
Haloalkenyloxycarbonyloxy: group of the formula R-CO-O- in which R is a haloalkenyloxy group as defined above, for example C2-Cio-haloalkenyloxy, C2-C8- haloalkenyloxy, C2-C6-haloalkenyloxy or C2-C4-haloalkenyloxy.
Haloalkenyloxythiocarbonyloxy: group of the formula R-CS-O- in which R is a haloalkenyloxy group as defined above, for example C2-Cio-haloalkenyloxy, C2-C8- haloalkenyloxy, C2-C6-haloalkenyloxy or C2-C4-haloalkenyloxy.
Alkynyloxycarbonyloxy: group of the formula R-CO-O- in which R is an alkynyloxy group as defined above, for example C2-Cio-alkynyloxy, C2-Cs-alkynyloxy, C2-C6- alkynyloxy or C2-C4-alkynyloxy. Alkynyloxythiocarbonyloxy: group of the formula R-CS-O- in which R is an alkynyloxy group as defined above, for example C2-Cio-alkynyloxy, C2-C8-alkynyloxy, C2-C6- alkynyloxy or C2-C4-alkynyloxy.
Haloalkynyloxycarbonyloxy: group of the formula R-CO-O- in which R is a haloalkynyloxy group as defined above, for example C2-Cio-haloalkynyloxy, C2-C8- haloalkynyloxy, C2-C6-haloalkynyl or C2-C4-haloalkynyloxy.
Haloalkynyloxythiocarbonyloxy: group of the formula R-CS-O- in which R is a haloalkynyloxy group as defined above, for example C2-Cio-haloalkynyloxy, C2-C8- haloalkynyloxy, C2-C6-haloalkynyl or C2-C4-haloalkynyloxy.
Cycloalkyloxycarbonyloxy: group of the formula R-CO-O- in which R is a cycloalkyloxy group as defined above, for example C3-Cio-cycloalkyloxy, Cs-Cs-cycloalkyloxy, C3-C6- cycloalkyloxy or Cs-Cβ-cycloalkyloxy.
Cycloalkyloxythiocarbonyloxy: group of the formula R-CS-O- in which R is a cycloalkyloxy group as defined above, for example C3-Cio-cycloalkyloxy, Cs-Cs- cycloalkyloxy, C3-C6-cycloalkyloxy or Cs-Cβ-cycloalkyloxy.
Cycloalkenyloxycarbonyloxy: group of the formula R-CO-O- in which R is a cycloalkenyloxy group as defined above, for example C3-Cio-cycloalkenyloxy, C3-C8- cycloalkenyloxy, Cs-Cβ-cycloalkenyloxy or Cs-Cβ-cycloalkenyloxy.
Cycloalkenyloxythiocarbonyloxy: group of the formula R-CS-O- in which R is a cycloalkenyloxy group as defined above, for example C3-Cio-cycloalkenyloxy, C3-C8- cycloalkenyloxy, Cs-Cβ-cycloalkenyloxy or Cs-Cβ-cycloalkenyloxy.
Alkylamino: group of the formula RHN- in which R is an alkyl group as defined above.
Dialkylamino: group of the formula RRN- in which each R independently is an alkyl group as defined above.
Alkylaminocarbonyl: group of the formula RHN-CO- in which R is an alkyl group as defined above.
Dialkylaminocarbonyl: group of the formula RRN-CO- in which each R independently is an alkyl group as defined above.
Alkylaminothiocarbonyl: group of the formula RHN-CS- in which R is an alkyl group as defined above. Dialkylaminothiocarbonyl: group of the formula RRN-CS- in which each R independently is an alkyl group as defined above.
Alkylaminocarbonyloxy: group of the formula RHN-CO-O- in which R is an alkyl group as defined above.
Dialkylaminocarbonyloxy: group of the formula RRN-CO-O- in which each R independently is an alkyl group as defined above.
Alkylaminothiocarbonyloxy: group of the formula RHN-CS-O- in which R is an alkyl group as defined above.
Dialkylaminothiocarbonyloxy: group of the formula RRN-CS-O- in which each R independently is an alkyl group as defined above.
Alkylthio: alkyl as defined above which is attached via a sulfur atom.
Haloalkylthio: haloalkyl as defined above which is attached via a sulfur atom.
Alkylsulfinyl (sometimes also referred to as alkylsulfoxyl): alkyl as defined above which is attached via an SO group.
Alkylsulfonyl: alkyl as defined above which is attached via an S(0)2 group.
Aryl: carbocyclic aromatic radical having 6 to 14 carbon atoms, such as phenyl, naphthyl, anthracenyl or phenanthrenyl. Cβ-Cio-Aryl is phenyl or naphthyl.
Aryloxy: carbocyclic aromatic radical having 6 to 14 carbon atoms which is attached via oxygen, such as phenoxy, naphthyloxy, anthracenyloxy or phenanthrenyloxy. Cβ-Cio- Aryloxy is phenoxy or naphthoxy.
Arylthio: carbocyclic aromatic radical having 6 to 14 carbon atoms which is attached via sulfur, such as phenylthio, naphthylthio, anthracenylthio or phenanthrenylthio. Cβ-Cio- Arylthio is phenylthio or naphthylthio.
Arylalkyl: alkyl (as defined above), for example d-Cs-alkyl, Ci-Cβ-alkyl or Ci-C4-alkyl, where a hydrogen atom is replaced by an aryl group, such as benzyl, phenethyl and the like.
Arylalkoxy: alkoxy (as defined above), for example Ci-Cs-alkoxy, Ci-Cβ-alkoxy or Ci- C4-alkoxy, where one hydrogen atom is replaced by an aryl group, such as benzyloxy, phenethyloxy and the like. 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10- membered saturated, partially unsaturated nonaromatic carbocyclic ring optionally containing as ring members 1 or 2 groups selected from C(=O) and C(=S): C3-Cio-cycloalkyl or C3-Cio-cycloalkenyl as defined above or a C3- Cio-cycloalkyl or C3-Cio-cycloalkenyl in hich one or two CH2 groups are replaced by 1 or 2 groups selected from C(=O) and C(=S), such as cyclopropanonyl, cyclopropenonyl, cyclobutanonyl, cyclopentanonyl cyclohexanonyl and cycloheptanonyl.
3-, 4-, 5-, 6-, 7-, 8-, 9- or 10- membered saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms from the group consisting of oxygen, nitrogen (as N or NR) and sulfur (as S, SO or SO2) and optionally 1 or 2 groups selected from C(=O) and C(=S) as ring members:
- three-, four-, five- or six-membered saturated or partially unsaturated heterocycle (hereinbelow also referred to as heterocyclyl) which contains one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen (as N or NR) and sulfur (as S, SO or SO2) and optionally 1 or 2 groups selected from C(=O) and C(=S) as ring members: for example monocyclic saturated or partially unsaturated heterocycles which, in addition to carbon ring members, contain one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms and optionally 1 or 2 groups selected from C(=O) and C(=S), for example 2-oxiranyl, 2-thiiranyl, 1- or 2-aziridinyl, 1-, 2- or 3-azetidinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 3-tetrahydrofuran-2-onyl, 4-tetrahydrofuran-2-onyl, 5-tetrahydrofuran-2-onyl, 2-tetrahydrofuran-3-onyl,
4-tetrahydrofuran-3-onyl, 5-tetrahydrofuran-3-onyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 3-tetrahydrothien-2-onyl, 4-tetrahydrothien-2-onyl, 5-tetrahydrothien-2-onyl, 2-tetrahydrothien-3-onyl, 4-tetrahydrothien-3-onyl, 5-tetrahydrothien-3-onyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 1 -pyrrolidin-2-onyl, 3-pyrrolidin-2-onyl, 4-pyrrolidin-2-onyl, 5-pyrrolidin-2-onyl, 1 -pyrrolidin-3-onyl,
2-pyrrolidin-3-onyl, 4-pyrrolidin-3-onyl, 5-pyrrolidin-3-onyl, 1-pyrrolidin-2,5-dionyl, 3-pyrrolidin-2,5-dionyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-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-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-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-dihydropyrazol-1 -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-hexahydrotriazin-2-yl and
1 ,2,4-hexahydrotriazin-3-yl and also the corresponding -ylidene radicals;
a seven-membered saturated or partially unsaturated heterocycle which contains one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur as ring members: for example mono- and bicyclic heterocycles having
7 ring members which, in addition to carbon ring members, contain one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, for example tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro[1 H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -A-, -5-, -6- or -7-yl,
2,3,4,7-tetrahydro[1 H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, hexahydroazepin-1-, -2-, -3- or -4-yl, tetra- and hexahydrooxepinyl, such as 2,3,4,5-tetrahydro[1 H]oxepin-2-, -3-, -A-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1 H]oxepin-2-, -3-, -A-, -5-, -6- or -7-yl,
2,3,6,7-tetrahydro[1 H]oxepin-2-, -3-, -A-, -5-, -6- or -7-yl, hexahydroazepin-1-, -2-, -3- or -4-yl, tetra- and hexahydro-1 ,3-diazepinyl, tetra- and hexahydro-1 ,4-diazepinyl, tetra- and hexahydro-1 ,3-oxazepinyl, tetra- and hexahydro-1 ,4-oxazepinyl, tetra- and hexahydro-1 ,3-dioxepinyl, tetra- and hexahydro-1 ,4-dioxepinyl and the corresponding -ylidene radicals.
a five- or six-membered aromatic heterocycle (= heteroaromatic radical) which contains one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur, for example 5-membered heteroaryl which is attached via carbon and contains one to three nitrogen atoms or one or two nitrogen atoms and one 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-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 and 1 ,3,4-triazol-2-yl; 5-membered heteroaryl which is attached via nitrogen and contains 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, which contains one, two or 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;
alkylene: divalent branched or preferably unbranched chains having 1 to 8 carbon atoms, for example CH2, CH2CH2, -CH(CH3)-, CH2CH2CH2, CH(CH3)CH2, CH2CH(CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2CH2 und CH2CH2CH2CH2CH2CH2CH2CH2.
oxyalkylene: divalent unbranched chains of 2 to 4 CH2 groups where one valency is attached to the skeleton via an oxygen atom, for example OCH2CH2, OCH2CH2CH2 and OCH2CH2CH2CH2;
oxyalkyleneoxy: divalent unbranched chains of 1 to 3 CH2 groups where both valencies are attached to the skeleton via an oxygen atom, for example OCH2O, OCH2CH2O and OCH2CH2CH2O.
alkenylene: aliphatic divalent unbranched chains of 2 to 6 chain members having a C-C double bond in any position, for example CH=CH, CH2CH=CH, CH2CH=CHCH2, CH=CHCH2CH2, CH=CHCH2CH2CH2, CH2CH=CHCH2CH2, CH=CHCH2CH2CH2CH2, CH2CH=CHCH2CH2CH2 and CH2CH2CH=CHCH2CH2;
alkynylene: aliphatic divalent unbranched chains of 2 to 6 chain members having a C-C triple bond in any position, for example CH≡CH, CH2C≡C, CH2C≡CCH2, C≡CCH2CH2, C=CCH2CH2CH2, CH2C=CCH2CH2, C=HCH2CH2CH2CH2, CH2C=CCH2CH2CH2 and CH2CH2C=CCH2CH2;
The statements below with respect to suitable and preferred features of the compounds according to the invention, especially with respect to their substituents R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R61, R62, R63, R64, R65, R66, L1, L2, L3, L4, L5, Ra, Rb, Rc, Rd, Re, Rf, Re, Rh, R', RJ, Rk, R", Rm, R", R0, RP, RO, Rr, Rα, Rβ, RA, RB, RD, RE, RF, RG, RH, Rπ , Rx, Ry, Rz, Ra1, Rb1, T, T1, T2, T3, V1, W, W1, X1, X11, X2, Y, Y1, Y2, Z, A, A', A", A1 and A2 and the indices a, b, c, m, n, q, p and p1 and their use, are valid both per se and, in particular, in every possible combination with one another. A is preferably O or S and more preferably O.
In one embodiment of the invention, in compounds of the general formula I R1 is preferably a radical R1' selected from the group consisting of Ci-Cio-alkyl, C2-C10- alkenyl, C2-Cio-alkynyl, C3-Cio-cycloalkyl-Ci-C4-alkyl, C3-Cio-cycloalkenyl-Ci-C4-alkyl, a 3- to 10-membered saturated or partially unsaturated non-aromatic carbocyclic ring optionally containing as ring members one or two groups selected from C(=O) and C(=S), phenyl, naphthyl, a 3- to 10-membered saturated or partially unsaturated non- aromatic heterocyclic ring attached via a carbon atom and containing 1 , 2, 3 or 4 heteroatoms selected from O, S and N as ring members and optionally containing as ring members one or two groups selected from C(=O) and C(=S), or a 5- or 6-membered heteroaromatic ring attached via a carbon atom and containing 1 , 2, 3 or 4 heteroatoms selected from O, S and N as ring members; where R1 may be partially or fully halogenated and/or may carry 1 , 2, 3 or 4 identical or different substituents L3, which are as defined above.
More preferably, R1' is Ci-Cio-alkyl, Cs-Cs-alkenyl, Cs-Cs-alkynyl, Cs-Cβ-cycloalkyl, C5-C6-cycloalkenyl, where the two last-mentioned groups may carry a Ci-C4-alkylidene group, or is phenyl or a 5- or 6-membered saturated or aromatic heterocycle which is attached via carbon. R1' may be partially or fully halogenated or carry one, two, three or four identical or different groups L3, which are as defined above.
If R1' carries one, two, three or four, preferably one, two or three, identical or different groups L3, L3 is preferably selected from the group consisting of halogen, cyano, nitro hydroxyl, Ci-Cβ-alkyl, C-i-Cβ-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Cβ-alkoxy, C-i-Ce-alkylthio, d-Ce-alkylsulfinyl, d-Ce-alkylsulfonyl, d-Ce-alkylcarbonyl, Ci-C6- alkoxycarbonyl, Ci-Cβ-alkoximino, C2-C6-alkenyloximino, trimethylsilyl, C2-C6- alkynyloximino, Cs-Cβ-cycloalkyl, Cs-Cβ-cycloalkenyl, phenyl, and 5- or 6-membered saturated or aromatic heterocycle which is attached via carbon where the aliphatic, alicyclic, aromatic or heterocyclic groups for their part may be partially or fully halogenated or may carry one, two or three groups L4.
If L3 carries at least one group L4, L4 is preferably selected from the group consisting of halogen, cyano, Ci-Cβ-alkyl, C-i-Cβ-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C-i-Cβ- alkylcarbonyl, Ci-Cβ-haloalkylcarbonyl and C-i-Cβ-alkoxy.
Even more preferably, R1' is Ci-Cio-alkyl, Cs-Cs-alkenyl, Cs-Cs-alkynyl, C3-C6- cycloalkyl, Cs-Cβ-cycloalkenyl, phenyl, a 5- or 6-membered saturated or aromatic heterocycle, phenyl bound via CH2 or a 5- or 6-membered saturated or aromatic heterocycle bound via CH2, here R1' may be partially or fully halogenated or carry one, two, three or four identical or different groups L3, which are as defined above. Particularly preferably, R1' is Ci-Cs-alkyl, especially branched Cs-Cs-alkyl, Ci-Cβ- haloalkyl, Cs-Cs-alkenyl, especially branched Cs-Cs-alkenyl, Cs-Cβ-cycloalkyl, which may carry a Ci-C4-alkyl group, or Cs-Cβ-cycloalkenyl, which may carry a Ci-C4-alkyl group. More preferably, R1 is branched Cs-Cs-alkyl, such as isopropyl, sec-butyl, isobutyl (2-methylpropyl), tert-butyl, 2- and 3-pentyl, 2- and 3-methylbutyl, 1 ,1- dimethylpropyl, 2,2-dimethylpropyl, 2-and 3-hexyl, 2-, 3- and 4-methylpentyl and the like. The branch point is preferably not at the carbon atom through which the radical R1' is attached to the pyrazine ring. Examples of such alkyl radicals are isobutyl, 2- and 3- methylbutyl, 2,2-dimethylpropyl, 2-, 3- and 4-methylpentyl and the like. Specifically, R1' is isobutyl (2-methylpropyl) or 2-methylbutyl.
Alternatively, in compounds of the general formula I, R1 is preferably a group NR5R6.
Here, R5 is preferably d-Cs-alkyl, d-Cs-haloalkyl, Ci-Cs-hydroxyalkyl, Ci-d-alkoxy- Ci-C4-alkyl, Ci-Cs-alkyl which carries a substituent selected from the group consisting of COOH, Ci-C4-alkoxycarbonyl, aminocarbonyl, d-Cs-alkylaminocarbonyl, di-(Ci-Cs- alkyl)aminocarbonyl and Ci-d-alkylcarbonyloxy, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci- d-alkyl or phenyl which optionally carries 1 , 2 or 3 substituents selected from the group consisting of halogen, d-d-alkoxy and d-d-alkyl.
Particularly preferably, R5 is straight-chain or branched Ci-Cs-alkyl or straight-chain or branched Ci-Cs-haloalkyl, straight-chain or branched Cs-Cs-alkyl and straight-chain or branched C2-Cs-haloalkyl being more preferred. Even more preferably, R5 is branched Cs-Cβ-alkyl, straight-chain C2-C6-haloalkyl or branched Cs-Cβ-haloalkyl.
Here, branched Cs-Cβ-alkyl is, for example, isopropyl, sec-butyl, isobutyl, tert-butyl, 1-methylpropyl, 2- and 3-pentyl, 2- and 3-methylbutyl, 1 ,1-dimethylpropyl, 2,2-dimethylpropyl, 1 ,2-dimethylpropyl, 2- and 3-hexyl, 2-, 3- and 4-methylpentyl, 1 ,2,2-trimethylpropyl and the like. Particularly preferably, the branched Cs-Cβ-alkyl radical has a branching point at the 1 -position of the (starting from the nitrogen atom to which the radical R5 is attached) longest carbon chain of the alkyl radical, i.e. in the α-position to the nitrogen atom, and optionally a further branching point at a further carbon atom of the alkyl group, in particular at the 2-position of the longest carbon chain of the alkyl radical. Examples of these are isopropyl, sec-butyl, tert-butyl, 1-methylpropyl, 2-pentyl, 2-methylbutyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, 2-hexyl, 2-methylpentyl, 1 ,2,2-trimethylpropyl and the like.
The straight-chain or branched C2-Cs-haloalkyl radical is preferably a fluorinated C2-C8- alkyl radical. The fluorinated C2-Cs-alkyl radical preferably has 1 , 2, 3, 4, 5 or 6 fluorine atoms, particularly preferably 1 , 2 or 3 and especially 2 or 3 fluorine atoms. Preferably, the fluorine atoms are not attached to the carbon atom of the haloalkyl radical which is attached directly to the nitrogen atom which carries the radical R5. Particularly preferably, the fluorine atoms are attached in the 2- and/or 3-position of the (starting from the nitrogen atom to which the radical R5 is attached) longest carbon chain of the haloalkyl radical. Preferably, the branched Cs-Cs-haloalkyl radical has a branching point at the 1 -position of the (starting from the nitrogen atom to which the radical R5 is attached) longest carbon chain of the haloalkyl radical, i.e. at the α-position to the nitrogen atom, and optionally a further branching point at a further carbon atom of the haloalkyl group, for example at the 2- and/or 3-position of the longest carbon chain of the haloalkyl radical.
The straight-chain or branched C2-C8-haloalkyl radical is especially a fluorinated C2-C3- alkyl radical, for example 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-fluoro-i- methylethyl, 2,2-difluoro-1 -methylethyl, 1 -methyl-2,2,2-trifluoroethyl, bis(fluoromethyl)methyl, bis(difluoromethyl)methyl, bis(trifluoromethyl)methyl and the like.
R6 is preferably H or has one of the inventive or preferred meanings given for R5. Particularly preferably, R6 is H or Ci-C4-alkyl, more preferably H, methyl or ethyl and in particular H or methyl. In a special embodiment of the invention, R6 is H. In case R6 is H, R5 is preferably different from H.
In an alternative preferred embodiment of the invention, R6 is #-CR61R62-(CR63R64)q-(CR65R66)p-Y-Z in which # is the point of attachment to the nitrogen atom and R61, R62, R63, R64, R65, R66, Y, Z, p and q have the general meanings given above or the preferred meanings given below. In this case, R5 is preferably H or Ci-C4-alkyl, more preferably H, methyl or ethyl and in particular H or methyl. In a special embodiment of the invention, R5 is in this case H.
Here R61 is preferably straight-chain or branched Ci-Cs-alkyl, Cs-Cs-alkenyl or C3-C6- cycloalkyl, particularly preferably d-Cε-alkyl or Cs-Cβ-cycloalkyl, for example methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, sec-pentyl, cyclopropyl or cyclopentyl, preferably isopropyl, isobutyl, tert-butyl, sec-pentyl, cyclopropyl or cyclopentyl and in particular tert-butyl. In an alternative preferred embodiment, R61 is not hydrogen or methyl. In an alternative preferred embodiment, the group R61 has a branching point at the α-carbon atom. In an alternative preferred embodiment, the group R61 is substituted by groups attached via heteroatoms, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or formyl, carboxyl, alkoxycarbonyl, alkoxythiocarbonyl or alkenyl, alkynyl groups or C2-Cs-alkylene, where both valencies are attached to the same carbon atom. In an alternative preferred embodiment, the group R61 is substituted by Cs-Cβ-cycloalkyl or Cs-Cs-cycloalkenyl. In an alternative preferred embodiment, the group R61 is substituted by C(O)RA, C(O)ORA, C(S)ORA, C(O)NRARB, C(S)NRARB, C(NRA)RB, C(O)SRπ or C(S)SRπ . Here, Rπ is preferably d-Cs-alkyl or Cs-Cβ-cycloalkyl, where these groups may be partially or fully halogenated. In an alternative preferred embodiment, the group R61 is substituted by a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S.
In a preferred embodiment of the invention, R62 is hydrogen, straight-chain or branched Ci-Cs-alkyl or Cs-Cβ-cycloalkyl, in particular hydrogen, Ci-Cβ-alkyl or Cs-Cβ-cycloalkyl, preferably hydrogen, isopropyl or tert-butyl. If R62 is an alkyl group, R62 preferably has the same meaning as R61. In an alternative preferred embodiment, R61 and R62 together form a Cs-Cβ-alkylene, in particular a C3-C4-alkylene, group, where the carbon chains may be substituted by the groups attached via heteroatoms, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or alkoxycarbonyl. In an alternative preferred embodiment, R61 and R62 together form a Cs-Cβ-alkylene, in particular a C3-C4-alkylene, group, where the carbon chains are interrupted by one or two heteroatoms from the group consisting of O, N and S and may be substituted by groups attached via heteroatoms, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or alkoxycarbonyl.
In an alternative preferred embodiment, R62, R63 , R64 , R65 and R66 are each hydrogen or Ci-C4-alkyl, preferably hydrogen, methyl or ethyl, in particular hydrogen. The substitution of the groups R62, R63 , R64 , R65 and R66 corresponds preferably to that of the group R61.
In an alternative preferred embodiment, R61 and R63 together form a Cs-Cβ-alkylene, C3-C6-oxyalkylene or C2-C5-oxyalkyleneoxy, in particular a C3-C4-alkylene, group.
In an alternative preferred embodiment, R63 and R64 and/or R65 and R66 in each case together form a Cs-Cβ-alkylene, Cs-Cβ-oxyalkylene or C2-C5-oxyalkyleneoxy, in particular a C3-C4-alkylene, group.
In a preferred embodiment, the index q has the value zero or 1.
In a preferred embodiment, the index p is zero or 1 , in particular zero.
In an alternative preferred embodiment, R63 and R64 are preferably hydrogen if the index p has the value zero.
In an alternative preferred embodiment, R65 is not hydrogen and R66 is hydrogen if the index p is not zero. In an alternative preferred embodiment, the index p has the value zero or 1 and the index q has the value 1.
In an alternative preferred embodiment, R65 and R66 are preferably hydrogen. In an alternative preferred embodiment, R65 is not hydrogen and R66 is hydrogen.
In a preferred embodiment, Y is oxygen.
In one embodiment of the compounds of the formula I, Z is a monovalent group.
In a preferred embodiment, Z is selected from the group consisting of Ci-d-alkyl- carbonyl, in particular acetyl, n-propan-1-one, 2-methylpropan-1-one or butan-1-one, hydrogen, carboxyl, formyl, d-Cs-alkyl, d-Cs-haloalkyl, C2-C8-alkenyl, C2-C8- haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, Cs-drcycloalkyl, Cs-Cs-cycloalkenyl, C(O)Rπ , C(O)ORπ , C(S)ORπ , C(O)SRπ , C(S)SRπ , C(NRA)SRπ , C(S)Rπ ,
C(NRπ )NRARB, C(NRπ )RA, C(NRπ )ORA, C(O)NRARB, C(S)NRARB, Ci-C8-alkylsulfinyl, d-Cβ-alkylthio, Ci-C8-alkylsulfonyl, C(O)-Ci-C4-alkylene-NRAC(NRπ )NRARB, C(S)-Cr C4-alkylene-NRAC(NRπ )NRARB, C(NRπ )-Ci-C4-alkylene-NRAC(NRπ )NRARB, phenyl, naphthyl, a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S and which is attached directly or via a carbonyl, thiocarbonyl, Ci-C4-alkylcarbonyl or Ci-d-alkylthiocarbonyl group. The abovementioned groups Z can be substituted by one or more groups Rb1. In a further embodiment, the group Z is substituted by one, two, three or four groups Rb1, such as halogen, or basic or acidic groups, such as NRARB, guanidyl, amidyl, hydroxyl, carboxyl or sulfonic acids. Z is especially selected from the group consisting of H, formyl, d-d-alkylcarbonyl and Cs-drcycloalkylcarbonyl.
Preferably, the groups RA and RB are hydrogen, d-d-alkyl or d-d-haloalkyl, in particular hydrogen and methyl.
Rπ is preferably d-d-alkyl or d-d-haloalkyl, in particular methyl.
In a specific embodiment of the invention, in the group #-CR61R62-(CR63R64)q-(CR65R66)p-Y-Z, R61 is H or d-d-alkyl, R62 is H, R63 is H or d-d-alkyl, R64 is H, q is 0 or 1 , in particular 1 , p is 0, Y is O and Z is H, Ci-d-alkyl, formyl, Ci-d-alkylcarbonyl or Cs-drcycloalkylcarbonyl.
If R6 is a group #-CR61R62-(CR63R64)q-(CR65R66)P-Y-Z, R5 is preferably H, Ci-Cβ-alkyI or d-Cs-haloalkyl, particularly preferably H, d-d-alkyl or d-d-haloalkyl and in particular H or Ci-d-alkyl. In a further preferred embodiment of the invention, the group NR5R6 is ethylglycinol, leucinol, tert-leucinol, valinol, norvalinol, methioninol, phenylalaninol, lysinol, argininol, histidinol, asparaginol, glutaminol, serinol, isoleucinol, cysteinol, hydroxymethylpiperidine, cis-2-hydroxymethyl-4-methylpiperidine, trans-2-hydroxy- methyl-4-methylpiperidine, cyclohexylglycinol, cyclopentylglycinol, butylglycinol, pentylglycinol, cis-2-aminocyclohexanol, trans-2-aminocyclohexanol, cis-2-aminocyclo- pentanol, trans-2-aminocyclopentanol, cis-1-amino-2-hydroxyindane or trans-1-amino- 2-hydroxyindane, in each case attached via nitrogen.
In a special embodiment of the invention, neither R5 nor R6 is H, i.e. the radical R1 is a tertiary amine.
In an alternative preferred embodiment of the invention, R5 and R6 together with the nitrogen atom to which they are attached form a saturated or unsaturated 5- or 6-membered heterocycle, where the heterocycle may additionally contain a heteroatom or a heteroatom-containing group selected from the group consisting of O, N and NR'" as ring member, where R'" is H, d-Cs-alkyl, d-Cs-haloalkyl or C2-C8-hydroxyalkyl and in particular H or Ci-Cβ-alkyl, and where the heterocycle may carry 1 , 2 or 3 substituents selected from the group consisting of halogen, hydroxyl, d-Cs-alkyl, d-Cs-haloalkyl, C2-C8-hydroxyalkyl, d-Cs-alkoxy, and d-Cs-haloalkoxy. Particularly preferably, R5 and R6 together with the nitrogen atom to which they are attached form a saturated 5- or, in particular, 6-membered heterocycle, where the heterocycle may additionally contain a heteroatom or a heteroatom-containing group selected from the group consisting of O and NR"' as ring member, where R'" is H, d-Cs-alkyl, Ci-Cs- haloalkyl or C2-C8-hydroxyalkyl and in particular H or Ci-Cβ-alkyl, and where the hetreocycle may carry 1 or 2 substituents selected from the group consisting of halogen, hydroxyl, d-Cs-alkyl, d-Cs-haloalkyl, C2-C8-hydroxyalkyl, Ci-Cs-alkoxy and d-Cβ-haloalkoxy. Preferably, the heterocycle has, in addition to the nitrogen atom which carries the radicals R5 and R6, no further heteroatoms as ring members. If the heterocycle carries substituents, these are preferably selected from the group consisting of halogen, d-d-alkyl and d-d-haloalkyl and in particular from the group consisting of d-d-alkyl. Especially, the heterocycle carries a d-d-alkyl substituent, for example a methyl substituent.
In an alternative embodiment of the invention, R1 is a radical OR9. In a further alternative embodiment of the invention, R1 is a radical N=CR7R8.
Here, R9 is preferably not H. Preferably, R9 is d-C6-alkyl, d-Ce-haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl or Cs-Cβ-cycloalkyl. Particularly preferably, R9 is Ci-Cβ-alkyl, C2-C6-alkenyl or d-Cβ-haloalkyl which are in each case branched at the α-position. Alternatively, R9 is particularly preferably d-d-haloalkyl. R9 is in particular ethyl, propyl, isopropyl, 1 ,2-dimethylpropyl, 1 ,2,2-trimethylpropyl, 1-methyl-2,2,2-trifluoroethyl or 2,2,2-trifluoroethyl.
In a particularly preferred embodiment of the invention, R1 is a group R1' or a group NR5R6, where R1', R5 and R6 preferably have the preferred meanings given above. R1 is in particular a group R1', where R1' preferably has the preferred meanings given above.
In a preferred embodiment of the invention, the radical R2 is phenyl, pyridinyl, for example 2-, 3- or 4-pyridinyl, pyrimidinyl, for example 2-, 4- or 5-pyrimidinyl, pyrazinyl, for example 2-pyrazinyl, pyridazinyl, for example 3- or 4-pyridazinyl, triazinyl, furyl, for example 2- or 3-furyl, thienyl, for example 2- or 3-thienyl, pyrrolyl, for example 2- or 3-pyrrolyl, pyrazolyl, for example 1-, 3-, 4- or 5-pyrazolyl, imidazolyl, for example 1-, 2-, 4- or 5-imidazolyl, oxazolyl, for example 2-, 4- or 5-oxazolyl, isoxazolyl, for example 3-, 4- or 5-isoxazolyl, thiazolyl, for example 2-, 4- or 5-thiazolyl, isothiazolyl, for example 3-, 4- or 5-isothiazolyl, triazolyl, for example 1-, 4- or 5-[1 ,2,3]-1 H-triazolyl, 2-, 4- or 5-[1 ,2,3]-2H-triazolyl, 1 -, 3- or 5-[1 ,2,4]-1 H-triazolyl or 3-, 4- or 5-[1 ,2,4]-4H-triazolyl, oxadiazolyl, for example 4- or 5-[1 ,2,3]-oxadiazolyl, 3- or 5-[1 ,2,4]-oxadiazolyl or 2- or 5-[1 ,3,4]-oxadiazolyl, thiadiazolyl, for example 4- or 5-[1 ,2,3]-thiadiazolyl, 3- or 5- [1 ,2,4]-thiadiazolyl or 2- or 5-[1 ,3,4]-thiadiazolyl, or tetrazolyl, for example 1 -, 2- or 5-[1 ,2,3,4]tetrazolyl which carries a substituent L1 and 1 , 2 , 3 or 4, preferably 1 or 2, substituents L2, where L1 and L2 are defined as above or, preferably, as described below.
Particularly preferably, the radical R2 is phenyl, pyridinyl, for example 2-, 3- or 4- pyridinyl, pyrimidinyl, especially 4- or 5-pyrimidinyl, pyrazinyl, for example 2-pyrazinyl, pyridazinyl, for example 3- or 4-pyridazinyl, furyl, for example 2- or 3-furyl, thienyl, for example 2- or 3-thienyl, pyrazolyl, especially 1- or 5-pyrazolyl, imidazolyl, especially 1-, 2- or 5-imidazolyl, oxazolyl, for example 2-, 4- or 5-oxazolyl, isoxazolyl, for example 3-, 4- or 5-isoxazolyl, thiazolyl, for example 2-, 4- or 5-thiazolyl, isothiazolyl, for example 3-, 4- or 5-isothiazolyl, or triazolyl, especially 1-[1 ,2,4]-1 H-triazolyl which carries a substituent L1 and 1 , 2, 3 or 4, preferably 1 or 2, in particular 1 or 2, substituents L2, where L1 and L2 are defined as above, or, preferably, as described below.
In one particularly preferred embodiment of the invention, R2 is phenyl substituted by a radical L1 and 1 , 2, 3 or 4, preferably 1 or 2 radicals L2.
L2 is preferably selected from halogen, Ci-Cs-alkyl, for example Ci-C4-alkyl, Ci-Cs- haloalkyl, for example Ci-C4-haloalkyl, Ci-Cs-alkoxy, for example Ci-C4-alkoxy, Ci-Cs- haloalkoxy, for example Ci-C4-haloalkoxy, cyano, nitro, Ci-C4-alkoxycarbonyl, and aminocarbonyl. More preferably, L2 is selected from d-Cs-alkyl, for example Ci-C4- alkyl, d-Cs-haloalkyl, for example d-d-haloalkyl, Ci-Cs-alkoxy, for example C1-C4- alkoxy, and Ci-Cs-haloalkoxy, for example Ci-C4-haloalkoxy. Even more preferably, L2 is selected from halogen, such as fluorine or chlorine, Ci-C4-alkyl, such as methyl, Ci-C4-haloalkyl, such as trifluoromethyl, and Ci-C4-alkoxy, such as methoxy. Even more preferably L2 is selected from halogen, in particular fluorine or chlorine, C1-C4- alkyl, in particular methyl, and Ci-C4-alkoxy, in particular methoxy. Particularly preferably, L2 is selected from halogen and Ci-C4-alkyl and is especially halogen, such as chlorine or fluorine, or methyl. In particular, L2 is chlorine or fluorine and specifically fluorine.
Figure imgf000038_0001
Embodiments of the radical R2 relate in particular to phenyl groups which, in addition to the group L1, may have the following substituents: position 2: fluorine, chlorine, methyl, preferably fluorine or chlorine, in particular fluorine; position 3: hydrogen, fluorine, methoxy, the group L1; preferably hydrogen or the group L1; position 5: hydrogen, fluorine, chlorine, methyl, the group L1; particularly preferably hydrogen or the group L1; position 6: hydrogen, fluorine, chlorine, methyl; particularly preferably hydrogen or fluorine.
In six-membered rings R2, particularly in phenyl, as group R2, the radical L1 is preferably located in position 3, 4 or 5 (relating to the attachment point of R2 to the pyrazine moiety as position 1).
In a preferred embodiment of the invention, R2 is one of the groups A or B, group A being more preferred.
Figure imgf000038_0002
(m = 1 , 2, 3, 4)
Here, L2 is preferably one of the following substituent combinations: 2-CI; 2-F; 2-CH3; 6-CI; 6-F; 6-CH3; 2,6-F2; 2,6-Cl2; 2-F,6-CH3; 2-CH3,6-F; 2-CF3, 6-F; 2-OCH3,6-F; 2-F.6-
Cl; 2-CI.6-F; 2-CI.5-F; 2,3-F2; 2,5-F2; 2-CH3, 5F; 2,6-(CH3)2; 2-CH3,6-CI; 2-CH3,5-F.
Particularly preferably, L2 is one of the following substituent combinations: 2-F; 2-CI; 2-
CH3; 6-F; 6-CI; 6-CH3; 2,6-F2; 2-F.6-CI; 2-F,6-CH3 and even more preferably 2-F; 6-F and 2,6-F2.
The compounds of the formula I which carry groups A or B correspond to the formulae
I. A and I. B, group I. A being preferred.
Figure imgf000039_0001
(m = 1 , 2, 3, 4)
In a further embodiment of the invention, R2 is 5-membered heteroaryl which is substituted by a radical L1 and by 1 , 2 or 3 radicals L2. Here, the 5-membered heteroaryl ring is preferably selected from the group consisting of thienyl, for example 2- or 3-thienyl, pyrazolyl, for example 1-, 3-, 4- or 5-pyrazolyl, and thiazolyl, for example 2-, 4- or 5-thiazolyl.
In a further embodiment of the invention, R2 is 6-membered heteroaryl which contains 1 to 3 nitrogen atoms and is substituted by a radical L1 and by 1 , 2 or 3 radicals L2. Here, the 6-membered heteroaryl ring is preferably selected from the group consisting of pyridinyl, for example 2-, 3- or 4-pyridinyl, pyrimidinyl, for example 2-, 4- or 5-pyrimidinyl, pyrazinyl, for example 2-pyrazinyl, and pyridazinyl, for example 3- or 4-pyridazinyl.
In a preferred embodiment of the invention, R2 is pyridyl which is attached in the 2-, 3- or 4-position to the pyrazine ring and carries 1 , 2 or 3 identical or different substituents L2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred embodiment of such compounds are those of the formulae I. C and I. D, I. C being more preferred.
Figure imgf000039_0002
(m = 1 , 2, 3)
In an alternative preferred embodiment of the invention, R2 is pyrimidyl which is attached in the 2- or 4-position to the pyrazine ring and carries 1 or 2 identical or different substituents L2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred embodiment of such compounds are those of the formulae I. E and I. F, I. E being more preferred.
Figure imgf000040_0001
(m = 1 , 2)
In an alternative preferred embodiment of the invention, R2 is thienyl which is attached in the 2- or 3-position to the pyrazine ring and carries 1 or 2 identical or different substituents L2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred embodiment of such compounds are those of the formulae I. G and I. H.
Figure imgf000040_0002
(m = 1 , 2)
In an alternative preferred embodiment of the invention, R2 is thiazolyl which is attached in the 2-, 4- or 5-position to the pyrazine ring and carries a substituent L2 which is preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred embodiment of such compounds are those of the formulae I.I and IJ.
Figure imgf000040_0003
(m = 1 )
In an alternative preferred embodiment of the invention, R2 is imidazolyl which is attached in the 4- or 5-position to the pyrazine ring and carries 1 or 2 identical or different substituents L2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred embodiment of such compounds are those of the formulae I. K and I. L.
Figure imgf000041_0001
(m = 1 )
In an alternative preferred embodiment of the invention, R2 is pyrazolyl which is attached in the 1-, 3-, 4- or 5-position to the pyrazine ring and carries 1 or 2 identical or different substituents L2 which are preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred embodiment of such compounds are those of the formulae I. M, I.N and I.O.
Figure imgf000041_0002
(m = 1 )
In an alternative preferred embodiment of the invention, R2 is oxazolyl which is attached in the 2-, 3- or 4-position to the pyrazine ring and carries a substituent L2 which is preferably selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl. A preferred embodiment of such compounds are those of the formulae I. P and I. Q
Figure imgf000041_0003
(m = 1 )
In a preferred embodiment of the compounds I, in particular of the formulae LA to LQ, at least one group L2 is located in the ortho-position to the point of attachment of the group R2 to the pyrazine skeleton, in particular chlorine, fluorine or methyl.
In a further preferred embodiment, a heteroatom of the heteroaromatic radical R2 is located in the ortho-position to the point of attachment. If structurally possible, the index m is preferably 1 to 4, where the groups L2 may be identical or different. If the heteroaromatic groups R2 carry, in addition to a group L1, further substituents L2, these are preferably selected from the group consisting of: fluorine, chlorine, methyl, methoxy, cyano, nitro, alkoxycarbonyl, aminocarbonyl and haloalkyl. In a further embodiment, the substituents L2 are selected from the group consisting of fluorine, chlorine, methyl and methoxy. In a further embodiment, the substituents L2 are selected from the group consisting of fluorine, chlorine and methyl. A further embodiment relates to heteroaromatic groups R2 which, in addition to a group L1, are substituted by fluorine.
The radical R2 is in particular phenyl or pyridinyl, especially phenyl, where these carry a substituent L1 and 1 , 2, 3 or 4, preferably 1 or 2, in particular 1 or 2, substituents L2, where L1 and L2 are defined as above or as described below.
If R2 is phenyl or 2-pyridinyl, these rings preferably carry the substituent L1 in the 3-, 4- or 5-position, the 4-position being more preferred (based on the 1 -position of the bond to the pyrazine ring; i.e. L1 is particularly preferably attached in the meta- or, in particular, para-position to this point of attachment). The phenyl or the 2-pyridinyl ring has 1 or 2 further substituents L2. These are preferably attached in the 2- and/or 6- position of the phenyl ring (based on the 1 -position of the bond to the pyrazine ring), i.e. in the ortho-position to the point of attachment to the pyrazine ring, and in the case of the 2-pyridine ring preferably attached in the 6-position (based on the 1 -position of the bond to the pyrazine ring).
Among compounds I .A to I. Q, the compounds of formula I.A and I. B are most preferred. In these compounds, m is preferably 1 or 2, and each L2 is preferably bound in ortho position to the attachment point of the phenyl ring to the pyrazine moiety.
In a preferred embodiment of the invention, the substituent L1 of the radical R2 is is a group of the formula -Y1-Y2-T in which
Y1 is CRhR', C(O)O, C(O)NRh, O, NRh or S(O)r;
Y2 is d-Cs-alkylene, C2-Cs-alkenylene or C2-C8-alkynylene, where Y2 may be interrupted by one, two, three or four heteroatoms from the group consisting of NRh, O and S(O)r; r is O, 1 or 2;
T is ORh, NRhR', C(O)ORh, C(O)NRhR', C(NORh)R' or T1-C(=T2)-T3 in which T1 is O or NRh; T2 is O, S or NRh; T3 is Rh, ORh, SRh or NRhR'; Rh and R1, independently of each other, are hydrogen, d-Cs-alkyl, Cs-Cs-alkenyl, C3- Cs-alkynyl, Cs-Cβ-cycloalkyl or Cs-Cβ-cycloalkenyl. In a more preferred embodiment of the invention, the substituent L1 of the radical R2 is a radical L11 of the formula
Figure imgf000043_0001
in which
Aα is Ci-C4-alkylene; γα 1 γ α 2 jn(jepenc|ent|y of one another are O, S or NRhCt; "T is ORhα, SRhα or NRhαR'α;
Rhα and R'α independently of one another are H or Ci-C4-alkyl; and a is 1 , 2, 3 or 4.
Ci-C4-Alkylene in Aα is preferably methylene, 1 ,2-ethylene, 1 ,2- or 1 ,3-propylene or 1 ,4-n-butylene.
Aα is preferably methylene, 1 ,2-ethylene, 1 ,2-propylene or 1 ,3-propylene and in particular methylene or 1 ,2-ethylene.
γ«i and γα 2 independently of one another are preferably O or NRhCt. If Y™1 is O, Y™2 is also preferably O. Moreover, in this case Tα is preferably 0RhCt. If Y0"1 is NRhCtR'α and Y™2 is simultaneously O, Tα is in this case preferably 0Rhα.
"T is preferably 0Rh<χ or NRhCtR'α.
Rhα and R'α independently of one another are preferably H, methyl or ethyl.
a is preferably 1 , 2 or 3.
In another more preferred embodiment of the invention, the substituent L1 of the radical
R2 is a radical L12 of the formula Yβ-Aβ-Tβ in which
Yβ is CH2, O, S or NRhβR|β;
Aβ is C-i-Cs-alkylene;
Tβ is 0Rhβ, NRhβR|β or OC(=O)-"Pβ; T3β is Rhβ, 0Rhβ or NRhβR|β; and each Rhβ and R|β is independently H or Ci-C4-alkyl.
Yβ is preferably CH2 or O and especially O.
Aβ is preferably d-Cε-alkylene, in particular Ci-C4-alkylene.
Tβ is preferably 0Rhβ or NRhβR|β. Rhβ and R|β independently of one another are preferably H, methyl or ethyl and specifically methyl.
In another more preferred embodiment of the invention, the substituent L1 of the radical R2 is a radical L13 of the formula
in which
Y17 is -CONRh7 Or -COO; Aγ is C2-C6-alkylene;
Tγ is 0Rhγ, NRhγR'γ or OC(=O)-"Pγ;
T3γ is Rhγ, 0Rhγ or NRhγR'γ; and each Rhγ and R'γ is independently H or Ci-C4-alkyl.
Particularly preferably, the substituent L1 of the radical R2 is a radical L11 or L12 and specifically L12.
R3 is preferably halogen, Ci-Cio-alkyl, especially d-Cs-alkyl, Ci-Cio-haloalkyl, especially d-Cs-haloalkyl, Ci-Cio-alkoxy, especially d-Cs-alkoxy, Ci-Cio-haloalkoxy, especially d-Cs-haloalkoxy, or CN, particularly preferably halogen, d-d-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or CN, more preferably halogen, d-d-alkyl, especially Ci-C2-alkyl, or Ci-C4-haloalkyl, especially Ci-C2-haloalkyl. R3 is in particular halogen, especially chlorine, or d-d-alkyl, especially Ci-C2-alkyl, in particular methyl, and specifically halogen, especially chlorine.
In a preferred embodiment of the invention, R4 is a radical R4a which for its part is a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered, preferably 5- or 6-membered, saturated, partially unsaturated or aromatic heterocyclic ring having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members, where the heterocyclic ring may be partially or fully halogenated and/or may carry 1 , 2 or 3 radicals Rx, where Rx is as defined above.
The 5- or 6-membered heterocycles are preferably selected from the group consisting of pyrrolyl, such as 1-, 2- and 3-pyrrolyl; pyrrolinyl, such as 1-, 2- and 3-pyrrolinyl; pyrrolinonyl, pyrrolidinyl, such as 1-, 2- and 3-pyrrolidinyl; pyrrolidonyl, such as 1-, 3-, 4- and 5-pyrrolidin-2-onyl and also 1-, 2-, 4- and 5-pyrrolidin-3-onyl; pyrrolidindionyl, such as 1-pyrrolidin-2,5-dionyl; pyrazolyl, such as 1-, 3-, 4- and 5-pyrazolyl; pyrazolinyl, such as 1-, 3-, 4- and 5-pyrazolinyl; pyrazolidinyl, such as 1-, 2-, 3- and 4-pyrazolidinyl; pyrazolidinonyl; imidazolyl, such as 1-, 2-, 4- and 5-imidazolyl; imidazolinyl, such as 1-, 2-, 4- and 5-imidazolinyl; imidazolidinyl, such as 1-, 2- and 4-imidazolidinyl; imidazolidinonyl, such as 1- and 4-imidazolidin-2-onyl and also 1-, 2-, 3- and 5-imidazolidin-4-onyl; triazolyl, such as 1- and 2-[1 ,3,5]-(1 H)-triazolyl, 1-, 4- and 5- [1 ,2,3]-1 H-triazolyl, 2-, 4 and 5-[1 ,2,3]-2H-triazolyl and also 1-, 3- and 5-[1 ,2,4]-(1 H)- triazolyl; tetrazolyl, such as 1- and 5-[1 ,2,3,4]-(1 H)-tetrazolyl; thienyl, such as 2- and 3-thienyl; dihydrothienyl, such as 2,3-dihydrothien-2-, 3-, 4- and 5-yl; tetrahydrothienyl, such as tetrahydrothien-2- or 3-yl; tetrahydrothienonyl, such as tetrahydrothien-2-on-3-, 4- or 5-yl; dithiolanyl, such as 1 ,3-dithiolan-2- and 4-yl; furanyl, such as 2- and 3- furanyl; dihydrofuranyl, such as 2,3-dihydrofuran-2-, 3-, 4- and 5-yl; tetrahydrofuranyl, such as tetrahydrofuran-2- or 3-yl; tetrahydrofuranonyl, such as tetrahydrofuran-2-on-3- , 4- or 5-yl; tetrahydrofurandionyl, such as tetrahydrofuran-2, 5-dion-3-yl; dioxolanyl, such as 1 ,3-dioxolan-2- and 4-yl; thiazolyl, such as 2-, 4- and 5-thiazolyl; thiazolinyl, such as 2-, 4- and 5-thiazolinyl; thiazolidinyl, such as 2-, 4- and 5-thiazolidinyl; isothiazolyl, such as 3-, 4- and 5-isothiazolyl; isothiazolinyl, such as 3-, 4- and 5- isothiazolinyl; isothiazolidinyl, such as 3-, 4- and 5-isothiazolidinyl; oxazolyl, such as 2-,
4- and 5-oxazolyl; oxazolinyl, such as 2-, 4- and 5-oxazolinyl; oxazolidinyl, such as 2-, 3-, 4- and 5-oxazolidinyl, oxazolidinonyl, such as 3-, 4- and 5-oxazolidin-2-onyl; isoxazolyl, such as 3-, 4- and 5-isoxazolyl; isoxazolinyl, such as 3-, 4- and 5-isoxazolinyl; isoxazolidinyl, such as 3-, 4- and 5-isoxazolidinyl; isoxazolidinonyl, such as 2-, 4- and 5-isoxazolidin-3-onyl; thiadiazolyl, such as 4- and 5-[1 ,2,3]-thiadiazolyl, 3- and 5-[1 ,2,4]-thiadiazolyl and also 2- and 5-[1 ,3,4]-thiadiazolyl; oxadiazolyl, such as 4- and 5-[1 ,2,3]-oxadiazolyl, 3- and 5-[1 ,2,4]-oxadiazolyl and also 2- and 5-[1 ,3,4]- oxadiazolyl; pyridyl, such as 2-, 3- and 4-pyridyl; dihydropyridyl, such as 1 ,4-dihydropyrid-i-, 2-, 3- and 4-yl; dihydropyridinonyl, such as 1-, 3-, 4-, 5- and 6-(1 ,2- dihydro)-pyridin-2-onyl; tetrahydropyridyl, such as 1 ,2,3,6-tetrahydropyrid-1-, 2-, 3-, 4-,
5- and 6-yl and also 1 ,2,3,4-tetrahydropyrid-1-, 2-, 3-, 4-, 5- and 6-yl; tetrahydropyridinonyl, such as 1-, 3-, 4-, 5- and 6-(1 ,2,3,4-tetrahydro)pyridin-2-onyl; piperidyl, such as 1-, 2-, 3- and 4-piperidyl; pyrimidinyl, such as 2-, 4- and 5-pyrimidinyl; pyridazinyl, such as 2- and 3-pyridazinyl; pyrazinyl; piperazinyl, triazinyl, such as [1 ,2,4]- and [1 ,3,5]-triazinyl; morpholinyl, such as 1-, 2- and 3-morpholinyl; thiomorpholinyl, such as 1-, 2- and 3-thiomorpholinyl; pyranyl, such as 2-, 3- and 4-pyranyl; pyranonyl, such as pyran-4-on-2- or 3-yl; dihydropyranyl, such as
2,3-dihydropyran-2-, 3-, 4-, 5- and 6-yl; dihydropyranonyl, such as 2,3-dihydropyran-4- on-2-, 3-, 5- or 6-yl and 2,3-dihydropyran-6-on-2-, 3-, 4- or 5-yl; tetrahydropyranyl, such as 2-, 3- and 4-tetrahydropyranyl; tetrahydropyranonyl, such as tetrahydropyran-2-on- 3-, 4-, 5- or 6-yl and tetrahydropyran-4-on-2- or 3-yl; and dioxanyl, such as 1 ,4-dioxan- 2- or 3-yl or 1 ,3-dioxan-2- or 4-yl.
Preferably, the heterocyclic ring is unsubstituted or carries 1 or 2 substituents Rx selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy and in particular from the group consisting of nitro and Ci-C4-alkyl, especially nitro, methyl or ethyl.
In a preferred embodiment, the radical R4a is a 5- or 6-membered heteroaromatic ring which contains a nitrogen atom and optionally one or two further heteroatoms selected from the group consisting of O, N and S as ring members and which may be partially or fully halogenated and/or carry 1 , 2 or 3 radicals Rx, where Rx has the inventive or preferred meanings mentioned above (radical R4aa).
Preferably, R4aa is pyrrolyl, such as 1-, 2- and 3-pyrrolyl; pyrazolyl, such as 1-, 3-, 4- and 5-pyrazolyl; imidazolyl, such as 1-, 2-, 4- and 5-imidazolyl; triazolyl, 1- and 2-[1 ,3,5]-(1 H)-triazolyl, 1-, 4- and 5-[1 ,2,3]-1 H-triazolyl, 2-, 4 and 5-[1 ,2,3]-2H-triazolyl and also 1-, 3- and 5-[1 ,2,4]-(1 H)-triazolyl; tetrazolyl, such as 1- and 5-[1 ,2,3,4]-(1 H)- tetrazolyl; thiazolyl, such as 2-, 4- and 5-thiazolyl; isothiazolyl, such as 3-, 4- and 5-isothiazolyl; oxazolyl, such as 2-, 4- and 5-oxazolyl; isoxazolyl, such as 3-, 4- and 5-isoxazolyl; thiadiazolyl, such as 4- and 5-[1 ,2,3]-thiadiazolyl, 3- and 5-[1 ,2,4]- thiadiazolyl and also 2- and 5-[1 ,3,4]-thiadiazolyl; oxadiazolyl, such as 4- and 5-[1 ,2,3]- oxadiazolyl, 3- and 5-[1 ,2,4]-oxadiazolyl and also 2- and 5-[1 ,3,4]-oxadiazolyl; pyridyl, such as 2-, 3- and 4-pyridyl; pyrimidinyl, such as 2-, 4- and 5-pyrimidinyl; pyridazinyl, such as 2- and 3-pyridazinyl; pyrazinyl; or triazinyl, such as [1 ,2,4]- and [1 ,3,5]-triazinyl; where the heteroaromatic rings may be partially or fully halogenated and/or carry 1 , 2 or 3 radicals Rx, where Rx has the inventive or preferred meanings mentioned above or below.
Particularly preferably, R4aa is a 5-membered heteroaromatic ring which contains a nitrogen atom and optionally one or two further heteroatoms selected from the group consisting of O, N and S as ring members, such as pyrrolyl, such as 1-, 2- and 3- pyrrolyl; pyrazolyl, such as 1-, 3-, 4- and 5-pyrazolyl; imidazolyl, such as 1-, 2-, 4- and 5-imidazolyl; triazolyl, 1- and 2-[1 ,3,5]-(1 H)-triazolyl, 1-, 4- and 5-[1 ,2,3]-1 H-triazolyl, 2-, 4 and 5-[1 ,2,3]-2H-triazolyl and also 1-, 3- and 5-[1 ,2,4]-(1 H)-triazolyl; tetrazolyl, such as 1- and 5-[1 ,2,3,4]-(1 H)-tetrazolyl; thiazolyl, such as 2-, 4- and 5-thiazolyl; isothiazolyl, such as 3-, 4- and 5-isothiazolyl; oxazolyl, such as 2-, 4- and 5-oxazolyl; isoxazolyl, such as 3-, 4- and 5-isoxazolyl; thiadiazolyl, such as 4- and 5-[1 ,2,3]- thiadiazolyl, 3- and 5-[1 ,2,4]-thiadiazolyl and also 2- and 5-[1 ,3,4]-thiadiazolyl; and oxadiazolyl, such as 4- and 5-[1 ,2,3]-oxadiazolyl, 3- and 5-[1 ,2,4]-oxadiazolyl and also 2- and 5-[1 ,3,4]-oxadiazolyl; where the heteroaromatic rings may be partially or fully halogenated and/or carry 1 , 2 or 3 radicals Rx, where Rx has the inventive or preferred meanings mentioned above or below. Among these, preference is given to nitrogen-bound rings, such as 1-pyrrolyl, 1- pyrazolyl, 1-imidazolyl, 1- and 2-[1 ,2,3]-triazolyl, 1- and 2-[1 ,2,4]-triazolyl, and 1- or 2- [1 ,2,3,4]-tetrazolyl. Specifically, R4 is pyrazol-1-yl.
R4aa is preferably unsubstituted or carries 1 or 2 identical or different substituents Rx, which are as defined above or, preferably, selected from the group consisting of halogen, nitro, Ci-C4-alkyl and Ci-C4-haloalkyl and in particular from the group consisting of nitro and Ci-C4-alkyl, especially methyl. Specifically, R4aa is unsubstituted.
In an alternative preferred embodiment, the radical R4a is a 5- or 6-membered saturated or partially unsaturated nonaromatic heterocyclic ring which contains a nitrogen atom and optionally one or two further heteroatoms selected from the group consisting of O, N and S and/or one or two carbonyl groups as ring members and which may be partially or fully halogenated and/or carry 1 , 2 or 3 radicals Rx, where Rx has the inventive or preferred meanings mentioned above (radical R4ab).
R4ab is preferably a saturated heterocyclic radical selected from the group consisting of pyrrolidinyl, such as 1-, 2- and 3-pyrrolidinyl; pyrrolidonyl, such as 1-, 3-, 4- and 5-pyrrolidin-2-onyl and also 1-, 2-, 4- and 5-pyrrolidin-3-onyl; pyrrolidindionyl, such as 1-pyrrolidin-2,5-dionyl; pyrazolidinyl, such as 1-, 2-, 3- and 4-pyrazolidinyl; pyrazolidinonyl; imidazolidinyl, such as 1-, 2- and 4-imidazolidinyl; imidazolidinonyl, such as 1- and 4-imidazolidin-2-onyl and also 1-, 2-, 3- and 5-imidazolidin-4-onyl; thiazolidinyl, such as 2-, 4- and 5-thiazolidinyl; isothiazoidinlyl, such as 3-, 4- and 5-isothiazolidinyl; oxazolidinyl, such as 2-, 3-, 4- and 5-oxazolidinyl; oxazolidinonyl, such as 3-, 4- and 5-oxazolidin-2-onyl; isoxazolidinyl, such as 3-, 4- and
5-isoxazolidinyl; isoxazolidinonyl, such as 2-, 4- and 5-isoxazolidin-3-onyl; piperidyl, such as 1-, 2-, 3- and 4-piperidyl; morpholinyl, such as 1-, 2- and 3-morpholinyl; and thiomorpholinyl, such as 1-, 2- and 3-thiomorpholinyl. Alternatively, R4ab is a partially unsaturated heterocyclic radical. Examples of partially unsaturated (nonaromatic) heterocycles are pyrrolinyl, such as 1-, 2- and 3-pyrrolinyl; pyrrolinonyl, pyrazolinyl, such as 1-, 3-, 4- and 5-pyrazolinyl; imidazolinyl, such as 1-, 2-, 4- and 5-imidazolinyl; thiazolinyl, such as 2-, 4- and 5-thiazolinyl; isothiazolinyl, such as 3-, 4- and 5-isothiazolinyl; oxazolinyl, such as 2-, 4- and 5-oxazolinyl; isoxazolinyl, such as 3-, 4- and 5-isoxazolinyl; dihydropyridyl, such as 1 ,4-dihydropyrid-1-, 2-, 3- and 4-yl; dihydropyridinonyl, such as 1-, 3-, 4-, 5- and 6-(1 ,2-dihydro)pyridin-2-onyl; tetrahydropyridyl, such as 1 ,2,3,6-tetrahydropyrid-1-, 2-, 3-, 4-, 5- and 6-yl and also 1 ,2,3,4-tetrahydropyrid-1-, 2-, 3-, 4-, 5- and 6-yl; and tetrahydropyridinonyl, such as 1-, 3-, 4-, 5- and 6-(1 ,2,3,4-tetrahydro)pyridin-2-onyl. The heterocyclic radicals in R4ab can be partially or fully halogenated and/or carry 1 , 2 or 3 radicals Rx, where Rx has the inventive or preferred meanings mentioned above or below.
Particularly preferably, R4ab is pyrrolidonyl, such as 1-, 3-, 4- and 5-pyrrolidin-2-onyl and also 1-, 2-, 4- and 5-pyrrolidin-3-onyl; imidazolidinonyl, such as 1- and 4-imidazolidin-2- onyl and also 1-, 2-, 3- and 5-imidazolidin-4-onyl; oxazolidinonyl, such as 3-, 4- and 5-oxazolidin-2-onyl; isoxazolidinonyl, such as 2-, 4- and 5-isoxazolidin-3-onyl; or dihydropyridinonyl, such as 1-, 3-, 4-, 5- and 6-(1 ,2-dihydro)pyridin-2-onyl, where the heterocyclic rings may be partially or fully halogenated and/or carry 1 , 2 or 3 radicals Rx, where Rx has the inventive or preferred meanings given above or below.
R4ab is preferably unsubstituted or carries 1 or 2 identical or different substituents Rx which are as defined above or, preferably, selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl and in particular from the group consisting of Ci-C4-alkyl, especially methyl.
Specifically, R4ab is pyrazolinyl, especially 2-pyrazolinyl, which is unsubstituted or carries 1 or 2 identical or different substituents Rx which are preferably selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl and in particular from the group consisting of Ci-C4-alkyl, especially methyl.
In an alternative preferred embodiment of the invention, R4 is a radical R4c which for its part is a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered, preferably 5- or 6-membered, saturated, partially unsaturated or aromatic heterocyclic ring having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members, hich is fused to a phenyl ring, where the fused system may be partially or fully halogenated and/or may carry 1 , 2 or 3 radicals Rx, where Rx is as defined above.
The fused system is preferably selected from benzimidazolyl, benzothiazolyl, quinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl and benzotriazinyl.
In an alternative preferred embodiment of the invention, R4 is CN or a radical R4b of the formula -ON(=CRaRb), -NRcN=CRaRb, -N=ORa; -NRcC(=W)-NRaRb, -NRaC(=W)Rc, -NNRaRbC(=W)-X1-Rc, -OC(=W)RC, -O(C=W)NRaRb, -C(=W)RC, -C(=W)NRaRb, -C(=W)NORb, -CRaRb-C(=W)Rc, -C(=W)-NRa-X2-Rb, -C(=NX2Ra)-ORb or -C(=NX2Ra)-SRb, where Ra, Rb, Rc, W, X1 and X2 are as defined above. In the radical R4b, Ra, Rb, Rc, Rd, Re and Rf are preferably selected from the group consisting of H, hydroxyl, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxy, where, if Ra, Rb, Rc or Rd are attached directly to an oxygen atom, they are not hydroxyl or Ci- C4-alkoxy.
In the radical R4b, Ra, Rb and Rc are particularly preferably selected from the group consisting of H, hydroxyl, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxy, where, if Ra, Rb or Rc are attached directly to an oxygen atom, they are not hydroxyl or C1-C4- alkoxy, and Rd, Re and Rf are selected from the group consisting of H and Ci-C4-alkyl.
In the radical R4b, X2 is preferably a bond or -CO- and in particular a bond.
In this embodiment of the invention, R4 is particularly preferably CN or a radical R4ba of the formula -NRaC(=O)Rc, -NRa-CN, -C(=O)-ORC, -C(=NRd)Rc, -C(=NRd)-NRa-X2-Rb, -C(=N-NRdRe)-NRa-X2-Rb, -C(=O)-NRa-X2-Rb or -C(=S)-NRa-X2-Rb,
in which
X2 is a single bond, -CO-, -CONH-, -COO-, -O- or -NRf, where the left part of the divalent radicals is attached to the nitrogen atom; Ra is hydrogen, hydroxyl, Ci-C4-alkyl, Ci-C4-alkoxy or Ci-C4-alkylcarbonyl; and
Rb, Rc, Rd, Re and Rf independently of one another are hydrogen, hydroxyl, Ci-C4-alkyl or Ci-C4-alkoxy, where, if Ra, Rb, Rc or Rd are attached directly to an oxygen atom, they are not hydroxyl or Ci-C4-alkoxy.
In the radical R4ba, Rb and Rc are particularly preferably selected from the group consisting of H, hydroxyl, Ci-C4-alkyl and Ci-C4-alkoxy and Ra is selected from the group consisting of H, hydroxyl, Ci-C4-alkyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxy, where, if Ra, Rb or Rc are attached directly to an oxygen atom, they are not hydroxyl or Ci-C4-alkoxy, and Rd, Re and Rf are selected from the group consisting of H and C1-C4- alkyl.
In the radical R4ba, X2 is preferably a bond or -CO- and in particular a bond.
In an alternative preferred embodiment of the invention, R4 is a radical R4c of the formula -NRaRb, -NRcNRaRb, -NRa-CN, -CRaRb-ORc, -CRaRb-SRc or -CRaRb-NRcRd, where Ra, Rb, Rc and Rd are as defined above. Ra, Rb, Rc and Rd are preferably independently H, Ci-C4-alkyl or Ci-C4-alkoxy and in particular H or Ci-C4-alkyl.
In an alternative preferred embodiment of the invention, R4 is a radical R4d of the formula
Figure imgf000050_0001
in which
x is O or i ;
X1 and X11 are independently oxygen or N-Rf;
Q is C(H)-R', C-R' , N-N(H)-Rf or N-Rf;
1^- is a single bond or a double bond;
Ra, Rb, Rc, Rf independently of one another are hydrogen, Ci-Cβ-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, Cs-Cβ-cycloalkyl or C4-C6-cycloalkenyl, or
Ra and Rb together with the nitrogen atom to which they are attached form a group
Figure imgf000050_0002
R9, Rs and R1 are defined like Rc and may furthermore be halogen or cyano; or
Rs together with the carbon atom to which it is attached forms a CO group;
where the aliphatic, alicyclic or aromatic groups in the radicals Ra, Rb, Rc, Rf, R9, Rs and/or R1 may be partially or fully halogenated and/or carry 1 , 2, 3 or 4 substituents Rv, where
Rv is halogen, cyano, d-Cs-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, C-i-Cβ-alkoxy, C2-Cio-alkenyloxy, C2-Cio-alkynyloxy, Cs-Cβ-cycloalkyl, Cs-Cβ-cycloalkenyl, C3-C6-cycloalkoxy or Cs-Cβ-cycloalkenyloxy, or two of the radicals Ra, Rb,
Rc or Rd together with the atoms to which they are attached form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocycle having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of N, O and S.
In an alternative preferred embodiment of the invention, R4 is a radical R4e of the formula
Figure imgf000051_0001
in which
X2 is a single bond, -CO-, -CONH-, -COO-, -O- or -NRf-, where the left part of the divalent radicals is attached to the nitrogen atom;
Rf is hydrogen, methyl or Ci-C4-alkylcarbonyl;
Rb is hydrogen, methyl, benzyl, trifluoromethyl, allyl, propargyl or methoxymethyl;
Rb#, Rd# are independently hydrogen, d-Ce-alkyl or C2-C6-alkynyl;
W is S or NRd#;
where the aliphatic groups in the radicals Rb, Rb#, Rd and/or Rf may carry one or two substituents Rw; where
Rw is halogen, ORZ, NHRZ, Ci-C6-alkyl, Ci-C4-alkoxycarbonyl, Ci-C4-acylamino, [1 ,3]dioxolane-Ci-C4-alkyl or [1 ,3]dioxane-Ci-C4-alkyl in which Rz is hydrogen, methyl, allyl or propargyl.
Among the above radicals R4, preference is given to radicals R4a and especially to R4a As regards preferred embodiments of radicals R4aa, reference is made to what has been said above.
A particular embodiment of the invention relates to compounds of the formulae 1.1.1 and 1.1.2
Figure imgf000051_0002
(1.1.1 ) (1.1.2)
in which L1 is as defined above and is preferably a radical L11, L12 or L13, in particular a radical L11 or L12 and specifically L12; L2a, L2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
Ci-C4-alkoxy or Ci-C4-haloalkoxy, preferably H, halogen or Ci-C4-alkyl, and more preferably H or halogen, where at least one of the radicals L2a, L2b is not H; R3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen; R4a has the meanings given above and is preferably a radical R4aa or R4ab and more preferably R4aa; and R5 and R6 have the meanings given above, preferably the meanings given as being preferred.
A further particular embodiment of the invention relates to compounds of the formulae 1.2.1 and I.2.2
Figure imgf000052_0001
(1.2.1 ) (I.2.2)
in which
L1 is as defined above and is preferably a radical L11, L12 or L13, in particular a radical L11 or L12 and specifically L12;
L2a, L2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, and more preferably H or halogen, where at least one of the radicals L2a, L2b is not H; R3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen; R4b' is CN or a radical R4b which has the general or preferably preferred meanings given above and is preferably CN or a radical R4ba; and
R5 and R6 have the meanings given above, preferably the meanings given as being preferred.
A further particular embodiment of the invention relates to compounds of the formulae 1.3.1 and I.3.2
Figure imgf000053_0001
(1.3.1 ) (1.3.1 )
in which
L1 is as defined above and is preferably a radical L11, L12 or L13, in particular a radical L11 or L12 and specifically L12; L2a, L2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, and more preferably H or halogen, where at least one of the radicals L2a, L2b is not H; R3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen;
R4c has the general or preferably preferred meanings given above; and R5 and R6 have the meanings given above, preferably the meanings given as being preferred.
A further particular embodiment of the invention relates to compounds of the formulae 1.4.1 and I.4.2
Figure imgf000053_0002
(1.4.1 ) (I.4.2)
in which
L1 is as defined above and is preferably a radical L11, L12 or L13, in particular a radical L11 or L12 and specifically L12; L2a, L2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, more preferably H or halogen, where at least one of the radicals L2a, L2b is not H; R3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen;
R4d has the general or preferably preferred meanings given above; and R5 and R6 have the meanings given above, preferably the meanings given as being preferred.
A further particular embodiment of the invention relates to compounds of the formulae 1.5.1 and I.5.2
Figure imgf000054_0001
(1.5.1 ) (I.5.2)
in which
L1 is as defined above and is preferably a radical L11, L12 or L13, in particular a radical L11 or L12 and specifically L12; L2a, L2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, preferably H or halogen, where at least one of the radicals L2a, L2b is not H; R3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen;
R4e has the general or preferably preferred meanings given above; and R5 and R6 have the meanings given above, preferably the meanings given as being preferred.
A further particular embodiment of the invention relates to compounds of the formulae 1.6.1 and I.6.2
Figure imgf000054_0002
(1.6.1 ) (I.6.2) in which
L1 is as defined above and is preferably a radical L11, L12 or L13, in particular a radical L11 or L12 and specifically L12; L2a, L2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, preferably H or halogen, where at least one of the radicals L2a, L2b is not H; R1' has the meanings given above, preferably the meanings given as being preferred; R3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen; and R4a has the meanings given above and is preferably a radical R4aa or R4ab and more preferably R4aa.
A further particular embodiment of the invention relates to compounds of the formulae 1.7.1 and I.7.2
Figure imgf000055_0001
(1.7.1 ) (I.7.2)
in which
L1 is as defined above and is preferably a radical L11, L12 or L13, in particular a radical L11 or L12 and specifically L12;
L2a, L2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, preferably H or halogen, where at least one of the radicals L2a, L2b is not H;
R1' has the meanings given above, preferably the meanings given as being preferred; R3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen; and
R4b' is CN or a radical R4b which has the general or preferably preferred meanings given above and is preferably CN or a radical R4ba. A further particular embodiment of the invention relates to compounds of the formulae 1.8.1 and I.8.2
Figure imgf000056_0001
(1.8.1 ) (I.8.2)
in which
L1 is as defined above and is preferably a radical L11, L12 or L13, in particular a radical L11 or L12 and specifically L12;
L2a, L2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, preferably H or halogen, where at least one of the radicals L2a, L2b is not H;
R1' has the meanings given above, preferably the meanings given as being preferred; R3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen; and
R4c has the general or preferably preferred meanings given above.
A further particular embodiment of the invention relates to compounds of the formulae 1.9.1 and I.9.2
Figure imgf000056_0002
(1.9.1 ) (I.9.2)
in which
L1 is as defined above and is preferably a radical L11, L12 or L13, in particular a radical L11 or L12 and specifically L12;
L2a, L2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, preferably H or halogen, where at least one of the radicals L2a, L2b is not H; R1' has the meanings given above, preferably the meanings given as being preferred; R3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen; and
R4d has the general or preferably preferred meanings given above.
A further particular embodiment of the invention relates to compounds of the formulae 1.10.1 and 1.10.2
Figure imgf000057_0001
(1.10.1 ) (1.10.2)
in which
L1 is as defined above and is preferably a radical L11, L12 or L13, in particular a radical L11 or L12 and specifically L12; L2a, L2b independently of one another are H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl,
Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C4-alkyl, preferably H or halogen, where at least one of the radicals L2a, L2b is not H; R1' has the meanings given above, preferably the meanings given as being preferred; R3 is halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C4-alkyl or cyano, in particular halogen or methyl, specifically halogen; and R4e has the general or preferably preferred meanings given above.
Among the above compounds, compounds of formulae 1.6.1 and 1.6.2 are particularly preferred.
Examples of preferred compounds of the general formula I are those of the formulae l.a, l.b, l.c, l.d, l.e and l.f
Figure imgf000058_0001
(I a) (I b)
Figure imgf000058_0002
(I c) (Ld)
Figure imgf000058_0003
in which the variables R1', R3, R4, R5, R6 and L1 have the general or preferred meanings given above and one of L21 and L22 is H and the other one has one of the general or preferred meanings given for L2 or both L21 and L22 have one of the general or preferred meanings given for L2.
Examples of particularly preferred compounds of the general formula I are the compounds I compiled in Tables 1 to 1912680 below. Moreover, the meanings mentioned for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
Table 1 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is pyrrolidin-2-on-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 2
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 5-methylpyrrolidin-2-on-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 3
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is pyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 4
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-methyl pyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 5
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-(trifluoromethyl)pyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 6
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-(tert-butyl)pyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 7
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-bromopyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 8
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-phenylpyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 9
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-cyanopyτazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 10 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 4-methylpyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 11 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 4-bromopyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 12 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 4-chloropyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 13 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 4-cyanopyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 14 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 4-phenylpyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 15 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 5-methylpyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 16 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 3,5-dimethylpyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A. Table 17
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 3-trifluoromethyl-5-methylpyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 18
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 3,4,5-trimethylpyrazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 19
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 1 H-pyrazolin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 20
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 3-methyl-1 H-pyrazolin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 21
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 3-phenyl-1 H-pyrazolin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 22
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 4-methyl-1 H-pyrazolin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 23
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is imidazol-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 24
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 1-methylimidazol-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 25
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is [1 ,2,3]-(1 H)-triazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 26
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is [1 ,2,3]-(2H)-triazol-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 27
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is [1 ,2,4]-(1 H)-triazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 28
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is [1 ,2,4]-(4H)-triazol-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 29
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 4,5-dibromo-[1 ,2,3]-(1 H)-triazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 30
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 4,5-dimethyl-[1 ,2,3]-(1 H)-triazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 31
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 2-methyl-[1 ,2,3]-(1 H)-triazol-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 32
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-methyl-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 33 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 3-trifluoromethyl-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 34 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 3-nitro-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 35 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 3-methylthio-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 36 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 3-bromo-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 37 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 3-chloro-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 38 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 3,5-dimethyl-[1 ,2,4]-(1 H)-triazol-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 39 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is thiazol-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A. Table 40
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is thiazol-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 41
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is isothiazol-3-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 42
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is oxazol-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 43
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is oxazol-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 44
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is isoxazol-3-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 45
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is [1 ,3,4]-thiadiazol-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 46
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is [1 ,2,3]-thiadiazol-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 47
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 3-chloro-[1 ,2,4]-thiadiazol-5-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 48
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-methyl-[1 ,2,4]-thiadiazol-5-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 49
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is [1 ,3,4]-oxadiazol-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 50
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is [1 ,2,3]-oxadiazol-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 51
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-methyl-[1 ,2,4]-oxadiazol-5-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 52
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is pyridin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 53
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-methylpyridin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 54
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 4-methylpyridin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 55
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 5-methylpyridin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 56 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 6-methylpyridin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 57 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-chloropyridin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 58 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 4-chloropyridin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 59 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 5-chloropyridin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 60 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 6-chloropyridin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 61 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is pyridazin-3-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 62 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 6-methylpyridazin-3-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A. Table 63
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 6-chloropyridazin-3-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 64
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is pyrimidin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 65
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is pyrimidin-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 66
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 4-chloropyrimidin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 67
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 5-chloropyrimidin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 68
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 4-methylpyrimidin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 69
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 4-methoxypyrimidin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 70
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 2-methylpyrimidin-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 71
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 2,6-dimethylpyrimidin-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 72
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 2-chloropyrimidin-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 73
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCHb)2-OH, R4 is pyrazin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 74
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-methylpyrazin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 75
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 3-chloropyrazin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 76
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 6-chloropyrazin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 77
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is [1 ,2,4]-triazin-3-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 78
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is [1 ,2,4]-triazin-5-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 79 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 4,6-dichloro-[1 ,3,5]-triazin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 80 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is N-methylbenzimidazol-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 81 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCHb)2-OH, R4 is benzoxazol-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 82 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is benzothiazol-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 83 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is benzothiazol-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 84 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 6-nitrobenzothiazol-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 85 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is quinolin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A. Table 86
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 4-methylquinolin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 87
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is isoquinolin-1-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 88
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is quinoxalin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 89
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 6-chloroquinoxalin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 90
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 7-chloroquinoxalin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 91
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is 6,7-dichloroquinoxalin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 92
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is quinazolin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 93
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is quinazolin-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 94
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 4-methylquinazolin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 95
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 2-methylquinazolin-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 96
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCHb)2-OH, R4 is 2-chloroquinazolin-4-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 97
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCHb)2-OH, R4 is cinnolin-3-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 98
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is [1 ,2,4]-benzotriazin-3-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 99
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is 1 ,8-naphthyridin-2-yl and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 100
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=O)OCH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 101
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=O)OCH(CH3)2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 102 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=O)NH2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 103 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=O)NHCH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 104 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=O)NHCH2CH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 105 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=O)NHCH2CH2CH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 106 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=O)NH(CH(CH3)2) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 107 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=O)NHCH2CF3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 108 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=O)NHCH2CN and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A. Table 109
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=O)NHCH2CH2OCH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 110
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=O)NHCH2CH2SCH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 11 1
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=O)NHCH2CH2S(O)CH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 112
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=O)NHCH2CH2S(O)2CH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 113
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=O)NHCH2CH2N(CH3)2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 114
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=O)NHCH2CH=CH2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 115
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=O)NHCH2C≡CH and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 116
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=O)NHCH2Si(CH3)3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 117
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=O)NHCH2CO2CH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 118
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=O)NH(cyclopropyl) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 119
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=O)N(CH3)2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 120
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=O)N(CH2CH3)2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 121
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=O)N(CH2)5 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 122
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=O)NH-C(=O)CH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 123
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=S)NH2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 124
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=NOH)OH and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 125 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=NOH)CH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 126 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=NOH)NH2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 127 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=NOCH3)CH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 128 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=NOCH3)NH2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 129 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=NOCH(CH3)2)CH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 130 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=NH)NH-C(=O)CH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 131 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -C(=N-NHCH3)CH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A. Table 132
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=N-1-piperidyl)CH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 133
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -C(=N-N(CH3)2)NH2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 134
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -NH-(CH(=O)) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 135
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -NH-(C(=O)CH3) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 136
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -NH-(C(=O)CH2CH3) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 137
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -N(CH3)(C(=O)CH3) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 138
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -N(H)(C(=O)OCH3) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 139
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -N(H)(C(=O)OCH2CH3) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 140
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -N(CH3)(C(=O)OCH3) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 141
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -N(OCH3)(C(=O)OCH3) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 142
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -NH-CO-NHCH3 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 143
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -N(H)(CN) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 144
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -N(CH3)(CN) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 145
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -NH-N(CH3)2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 146
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -NH-N(CH2)5 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 147
Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is -(OCH2)2-OH, R4 is -NH-N(CH2CH2OCH2CH2) and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 148 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -NH-N=C(CH3)2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 149 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -NH-N=C(CH2)4 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 150 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -NH-N=C(CH2)5 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 151 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -O-N=C(CH3)2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 152 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -O-N=C(CH2)4 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 153 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -O-N=C(CH2)5 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Table 154 Compounds of the formula I. a in which R3 is chlorine, L21 is F, L22 is H, L1 is
-(OCH2)2-OH, R4 is -0-N(CHs)2 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Tables 155 to 308 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -(OCH2)2-OCH3 instead of -(OCH2)2-OH.
Tables 309 to 462
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -(OCHb)2-OC2H5 instead of -(OCH2)2-OH.
Tables 463 to 616
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -(OCH2)3-OH instead of -(OCH2)2-OH.
Tables 617 to 770
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -(OCH2)3-OCH3 instead of -(OCH2)2-OH.
Tables 771 to 924 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -(OCH2)3-OC2H5 instead of -(OCH2)2-OH.
Tables 925 to 1078
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -(O-CH2CH2)2-OH instead of -(OCH2)2-OH.
Tables 1079 to 1232
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -(O-CH2CH2)2-OCH3 instead of -(OCH2)2-OH.
Tables 1233 to 1386
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -(O-CH2CH2)2-OC2H5 instead of -(OCH2)2-OH.
Tables 1387 to 1540 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -0-CH2CH2-OH instead of -(OCH2)2-OH.
Tables 1541 to 1694
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -0-CH2CH2-OCHs instead of -(OCH2)2-OH.
Tables 1695 to 1848
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -0-CH2CH2-OC2H5 instead of -(OCH2)2-OH.
Tables 1849 to 2002
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -0-CH2CH2CH2-OH instead of -(OCH2)2-OH.
Tables 2003 to 2156 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -0-CH2CH2CH2-OCHs instead of -(OCH2)2-OH. Tables 2157 to 2310
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -O-CH2CH2CH2-OCH2CH3 instead of -(OCH2)2-OH.
Tables 2311 to 2464
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -O-CH2CH2-NH2 instead of - (OCH2)2-OH.
Tables 2465 to 2618
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -O-CH2CH2-NHCH3 instead of -(OCH2)2-OH.
Tables 2619 to 2772 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -0-CH2CH2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 2773 to 2926
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -0-CH2CH2-NHC2H5 instead of -(OCH2)2-OH.
Tables 2927 to 3080
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -0-CH2CH2-N(C2Hs)2 instead of -(OCH2)2-OH.
Tables 3081 to 3234
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -O-CH2CH2CH2-NH2 instead of -(OCH2)2-OH.
Tables 3235 to 3388 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -O-CH2CH2CH2-NHCH3 instead of -(OCH2)2-OH.
Tables 3389 to 3542
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -0-CH2CH2CH2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 3543 to 3696
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -O-CH2CH2CH2-NHC2H5 instead of -(OCH2)2-OH.
Tables 3697 to 3850
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -0-CH2CH2CH2-N(C2Hs)2 instead of -(OCH2)2-OH.
Tables 3851 to 4004
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -0-CH2CH2CH2CH2-NH2 instead of -(OCH2)2-OH.
Tables 4005 to 4158 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -0-CH2CH2CH2CH2-NHCHS instead of -(OCH2)2-OH. Tables 4159 to 4312
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -O-CH2CH2CH2CH2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 4313 to 4466
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -O-CH2CH2CH2CH2-NHC2H5 instead of -(OCH2)2-OH.
Tables 4467 to 4620
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -O-ChbCI-bCI-bCI-b-N^Hs^ instead of -(OCH2)2-OH.
Tables 4621 to 4774 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 4775 to 4928
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 4929 to 5082
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2- NHCH3 instead of -(OCH2)2-OH.
Tables 5083 to 5236
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2- N(CHs)2 instead of -(OCH2)2-OH.
Tables 5237 to 5390 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2-O- C(O)H instead of -(OCH2)2-OH.
Tables 5391 to 5544
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)3-OH instead of -(OCH2)2-OH.
Tables 5545 to 5698
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)3-NH2 instead of -(OCH2)2-OH.
Tables 5699 to 5852
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)3- NHCH3 instead of -(OCH2)2-OH.
Tables 5853 to 6006
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)3- N(CHs)2 instead of -(OCH2)2-OH.
Tables 6007 to 6160 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)3-O- C(O)H instead of -(OCH2)2-OH. Tables 6161 to 6314
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-CH(CHs)- CH2-OH instead of -(OCH2)2-OH.
Tables 6315 to 6468
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-CH(CHs)- CH2-NH2 instead of -(OCH2)2-OH.
Tables 6469 to 6622
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-CH(CHs)- CH2-NHCH3 instead of -(OCH2)2-OH.
Tables 6623 to 6776 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-CH(CHs)- CH2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 6777 to 6930
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-CH(CHs)- CH2-O-C(O)H instead of -(OCH2)2-OH.
Tables 6931 to 7084
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-CH2- CH(CHs)-OH instead of -(OCH2)2-OH.
Tables 7085 to 7238
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-CH2- CH(CHs)-NH2 instead of -(OCH2)2-OH.
Tables 7239 to 7392 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-CH2- CH(CHs)-NHCH3 instead of -(OCH2)2-OH.
Tables 7393 to 7546
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-CH2- CH(CHs)-N(CHs)2 instead of -(OCH2)2-OH.
Tables 7547 to 7700
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-CH2- CH(CHs)-O-C(O)H instead of -(OCH2)2-OH.
Tables 7701 to 7854
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2-O- (CH2)2-OH instead of -(OCH2)2-OH.
Tables 7855 to 8008
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2-O- (CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 8009 to 8162 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2-O- (CH2)2-NHCHs instead of -(OCH2)2-OH. Tables 8163 to 8316
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CHz)z-O- (CHz)2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 8317 to 8470
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2-O- (CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 8471 to 8624
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2-NH- (CH2)2-OH instead of -(OCH2)2-OH.
Tables 8625 to 8778 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2-NH- (CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 8779 to 8932
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2-NH- (CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 8933 to 9086
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2-NH- (CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 9087 to 9240
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2-NH- (CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 9241 to 9394 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2- N(CH3)-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 9395 to 9548
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2- N(CH3)-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 9549 to 9702
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2- N(CH3)-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 9703 to 9856
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2- N(CH3)-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 9857 to 10010
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)NH-(CH2)2- N(CH3)-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 10011 to 10164 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- OH instead of -(OCH2)2-OH. Tables 10165 to 10318
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- NH2 instead of -(OCH2)2-OH.
Tables 10319 to 10472
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- NHCH3 instead of -(OCH2)2-OH.
Tables 10473 to 10626
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- N(CHs)2 instead of -(OCH2)2-OH.
Tables 10627 to 10780 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)-(CH2)2- 0-C(O)H instead of -(OCH2)2-OH.
Tables 10781 to 10934
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)-(CH2)3- OH instead of -(OCH2)2-OH.
Tables 10935 to 1 1088
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)3- NH2 instead of -(OCH2)2-OH.
Tables 1 1089 to 1 1242
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)-(CH2)3- NHCH3 instead of -(OCH2)2-OH.
Tables 1 1243 to 1 1396 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)-(CH2)3- N(CHs)2 instead of -(OCH2)2-OH.
Tables 1 1397 to 1 1550
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)-(CH2)3- 0-C(O)H instead of -(OCH2)2-OH.
Tables 1 1551 to 1 1704
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)- CH(CHs)-CH2-OH instead of -(OCH2)2-OH.
Tables 1 1705 to 1 1858
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)- CH(CHs)-CH2-NH2 instead of -(OCH2)2-OH.
Tables 1 1859 to 12012
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)- CH(CHS)-CH2-NHCHS instead of -(OCH2)2-OH.
Tables 12013 to 12166 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)- CH(CHs)-CH2-N(CHs)2 instead of -(OCH2)2-OH. Tables 12167 to 12320
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)- CH(CHs)-CH2-O-C(O)H instead of -(OCH2)2-OH.
Tables 12321 to 12474
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)-CH2- CH(CHs)-OH instead of -(OCH2)2-OH.
Tables 12475 to 12628
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)-CH2- CH(CHs)-NH2 instead of -(OCH2)2-OH.
Tables 12629 to 12782 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)-CH2- CH(CHS)-NHCH3 instead of -(OCH2)2-OH.
Tables 12783 to 12936
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)-CH2- CH(CHs)-N(CHs)2 instead of -(OCH2)2-OH.
Tables 12937 to 13090
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)-CH2- CH(CHs)-O-C(O)H instead of -(OCH2)2-OH.
Tables 13091 to 13244
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- O-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 13245 to 13398 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- O-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 13399 to 13552
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- O-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 13553 to 13706
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- O-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 13707 to 13860
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- O-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 13861 to 14014
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- NH-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 14015 to 14168 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- NH-(CH2)2-NH2 instead of -(OCH2)2-OH. Tables 14169 to 14322
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- NH-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 14323 to 14476
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- NH-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 14477 to 14630
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- NH-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 14631 to 14784 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- N(CH3)-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 14785 to 14938
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- N(CH3)-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 14939 to 15092
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CH3)-(CH2)2- N(CH3)-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 15093 to 15246
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)-(CH2)2- N(CH3)-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 15247 to 15400 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)N(CHs)-(CH2)2- N(CH3)-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 15401 to 15554
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 15555 to 15708
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 15709 to 15862
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2- NHCH3 instead of -(OCH2)2-OH.
Tables 15863 to 16016
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2- N(CHs)2 instead of -(OCH2)2-OH.
Tables 16017 to 16170 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-O- C(O)H instead of -(OCH2)2-OH. Tables 16171 to 16324
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)3-OH instead of -(OCH2)2-OH.
Tables 16325 to 16478
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is
Figure imgf000095_0001
instead of -(OCH2)2-OH.
Tables 16479 to 16632
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)3- NHCH3 instead of -(OCH2)2-OH.
Tables 16633 to 16786 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)3- N(CHs)2 instead of -(OCH2)2-OH.
Tables 16787 to 16940
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)3-O- C(O)H instead of -(OCH2)2-OH.
Tables 16941 to 17094
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-CH(CHs)- CH2-OH instead of -(OCH2)2-OH.
Tables 17095 to 17248
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-CH(CHs)- CH2-NH2 instead of -(OCH2)2-OH.
Tables 17249 to 17402 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-CH(CHs)- CH2-NHCH3 instead of -(OCH2)2-OH.
Tables 17403 to 17556
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-CH(CHs)- CH2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 17557 to 17710
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-CH(CHs)- CH2-O-C(O)H instead of -(OCH2)2-OH.
Tables 17711 to 17864
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-CH2- CH(CHs)-OH instead of -(OCH2)2-OH.
Tables 17865 to 18018
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-CH2- CH(CHs)-NH2 instead of -(OCH2)2-OH.
Tables 18019 to 18172 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-CH2- CH(CHS)-NHCH3 instead of -(OCH2)2-OH. Tables 18173 to 18326
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-CH2- CH(CHs)-N(CHs)2 instead of -(OCH2)2-OH.
Tables 18327 to 18480
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-CH2- CH(CHs)-O-C(O)H instead of -(OCH2)2-OH.
Tables 18481 to 18634
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-O- (CH2)2-OH instead of -(OCH2)2-OH.
Tables 18635 to 18788 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-O- (CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 18789 to 18942
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-O- (CH2)2-NHCHs instead of -(OCH2)2-OH.
Tables 18943 to 19096
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-O- (CH2)2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 19097 to 19250
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-O- (CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 19251 to 19404 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-NH- (CH2)2-OH instead of -(OCH2)2-OH.
Tables 19405 to 19558
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-NH- (CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 19559 to 19712
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-NH- (CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 19713 to 19866
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-NH- (CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 19867 to 20020
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2-NH- (CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 20021 to 20174 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2- N(CH3)-(CH2)2-OH instead of -(OCH2)2-OH. Tables 20175 to 20328
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2- N(CH3)-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 20329 to 20482
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2- N(CH3)-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 20483 to 20636
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2- N(CH3)-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 20637 to 20790 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -CH=CH-C(O)O-(CH2)2- N(CH3)-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 20791 to 20944
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- OH instead of -(OCH2)2-OH.
Tables 20945 to 21098
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- NH2 instead of -(OCH2)2-OH.
Tables 21099 to 21252
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-(CH2)2- NHCH3 instead of -(OCH2)2-OH.
Tables 21253 to 21406 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-(CH2)2- N(CHs)2 instead of -(OCH2)2-OH.
Tables 21407 to 21560
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-(CH2)2- 0-C(O)H instead of -(OCH2)2-OH.
Tables 21561 to 21714
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-(CH2)3- OH instead of -(OCH2)2-OH.
Tables 21715 to 21868
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-(CH2)3- NH2 instead of -(OCH2)2-OH.
Tables 21869 to 22022
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-(CH2)3- NHCH3 instead of -(OCH2)2-OH.
Tables 22023 to 22176 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-(CH2)3- N(CHs)2 instead of -(OCH2)2-OH. Tables 22177 to 22330
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-(CH2)3- 0-C(O)H instead of -(OCH2)2-OH.
Tables 22331 to 22484
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH- CH(CHs)-CH2-OH instead of -(OCH2)2-OH.
Tables 22485 to 22638
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH- CH(CHs)-CH2-NH2 instead of -(OCH2)2-OH.
Tables 22639 to 22792 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH- CH(CHS)-CH2-NHCHS instead of -(OCH2)2-OH.
Tables 22793 to 22946
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH- CH(CHs)-CH2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 22947 to 23100
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH- CH(CHs)-CH2-O-C(O)H instead of -(OCH2)2-OH.
Tables 23101 to 23254
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-CH2- CH(CHs)-OH instead of -(OCH2)2-OH.
Tables 23255 to 23408 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-CH2- CH(CHs)-NH2 instead of -(OCH2)2-OH.
Tables 23409 to 23562
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-CH2- CH(CHS)-NHCH3 instead of -(OCH2)2-OH.
Tables 23563 to 23716
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-CH2- CH(CHs)-N(CHs)2 instead of -(OCH2)2-OH.
Tables 23717 to 23870
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-CH2- CH(CHs)-O-C(O)H instead of -(OCH2)2-OH.
Tables 23871 to 24024
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-(CH2)2- O-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 24025 to 24178 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)NH-(CH2)2- O-(CH2)2-NH2 instead of -(OCH2)2-OH. Tables 24179 to 24332
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- O-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 24333 to 24486
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- O-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 24487 to 24640
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- O-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 24641 to 24794 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- NH-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 24795 to 24948
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- NH-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 24949 to 25102
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- NH-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 25103 to 25256
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- NH-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 25257 to 25410 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- NH-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 2541 1 to 25564
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- N(CH3)-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 25565 to 25718
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- N(CH3)-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 25719 to 25872
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- N(CH3)-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 25873 to 26026
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- N(CH3)-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 26027 to 26180 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)NH-(CH2)2- N(CH3)-(CH2)2-O-C(O)H instead of -(OCH2)2-OH. Tables 26181 to 26334
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-OH instead of -(OCH2)2-OH.
Tables 26335 to 26488
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 26489 to 26642
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-NHCHs instead of -(OCH2)2-OH.
Tables 26643 to 26796 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 26797 to 26950
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 26951 to 27104
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)S-OH instead of -(OCH2)2-OH.
Tables 27105 to 27258
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)S-NH2 instead of -(OCH2)2-OH.
Tables 27259 to 27412 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)S-NHCH3 instead of -(OCH2)2-OH.
Tables 27413 to 27566
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)S-N(CHs)2 instead of -(OCH2)2-OH.
Tables 27567 to 27720
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)S-O-C(O)H instead of -(OCH2)2-OH.
Tables 27721 to 27874
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- CH(CHs)-CH2-OH instead of -(OCH2)2-OH.
Tables 27875 to 28028
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- CH(CHs)-CH2-NH2 instead of -(OCH2)2-OH.
Tables 28029 to 28182 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- CH(CHS)-CH2-NHCHS instead of -(OCH2)2-OH. Tables 28183 to 28336
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- CH(CHs)-CH2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 28337 to 28490
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- CH(CHs)-CH2-O-C(O)H instead of -(OCH2)2-OH.
Tables 28491 to 28644
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- CH2-CH(CHs)-OH instead of -(OCH2)2-OH.
Tables 28645 to 28798 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- CH2-CH(CHs)-NH2 instead of -(OCH2)2-OH.
Tables 28799 to 28952
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- CH2-CH(CHS)-NHCHS instead of -(OCH2)2-OH.
Tables 28953 to 29106
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- CH2-CH(CHs)-N(CHs)2 instead of -(OCH2)2-OH.
Tables 29107 to 29260
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- CH2-CH(CHs)-O-C(O)H instead of -(OCH2)2-OH.
Tables 29261 to 29414 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-O-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 29415 to 29568
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-O-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 29569 to 29722
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-O-(CH2)2-NHCHs instead of -(OCH2)2-OH.
Tables 29723 to 29876
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-O-(CH2)2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 29877 to 30030
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-O-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 30031 to 30184 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-NH-(CH2)2-OH instead of -(OCH2)2-OH. Tables 30185 to 30338
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-NH-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 30339 to 30492
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-NH-(CH2)2-NHCHs instead of -(OCH2)2-OH.
Tables 30493 to 30646
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-N H-(CH2)2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 30647 to 30800 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-NH-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 30801 to 30954
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-N(CHs)-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 30955 to 31 108
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-N(CHs)-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 31 109 to 31262
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-N(CH3)-(CH2)2-NHCHs instead of -(OCH2)2-OH.
Tables 31263 to 31416 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-N(CH3)-(CH2)2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 31417 to 31570
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)N(CHs)- (CH2)2-N(CHs)-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 31571 to 31724
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)2- OH instead of -(OCH2)2-OH.
Tables 31725 to 31878
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)2- NH2 instead of -(OCH2)2-OH.
Tables 31879 to 32032
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)2- NHCH3 instead of -(OCH2)2-OH.
Tables 32033 to 32186 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)2- N(CHs)2 instead of -(OCH2)2-OH. Tables 32187 to 32340
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)2- 0-C(O)H instead of -(OCH2)2-OH.
Tables 32341 to 32494
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)3- OH instead of -(OCH2)2-OH.
Tables 32495 to 32648
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)3- NH2 instead of -(OCH2)2-OH.
Tables 32649 to 32802 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)3- NHCH3 instead of -(OCH2)2-OH.
Tables 32803 to 32956
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)3- N(CHs)2 instead of -(OCH2)2-OH.
Tables 32957 to 33110
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)3- 0-C(O)H instead of -(OCH2)2-OH.
Tables 3311 1 to 33264
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O- CH(CHs)-CH2-OH instead of -(OCH2)2-OH.
Tables 33265 to 33418 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O- CH(CHs)-CH2-NH2 instead of -(OCH2)2-OH.
Tables 33419 to 33572
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O- CH(CHS)-CH2-NHCHS instead of -(OCH2)2-OH.
Tables 33573 to 33726
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O- CH(CHs)-CH2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 33727 to 33880
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O- CH(CHs)-CH2-O-C(O)H instead of -(OCH2)2-OH.
Tables 33881 to 34034
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-CH2- CH(CHs)-OH instead of -(OCH2)2-OH.
Tables 34035 to 34188 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-CH2- CH(CHs)-NH2 instead of -(OCH2)2-OH. Tables 34189 to 34342
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-CH2- CH(CHs)-NHCH3 instead of -(OCH2)2-OH.
Tables 34343 to 34496
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-CH2- CH(CHs)-N(CHs)2 instead of -(OCH2)2-OH.
Tables 34497 to 34650
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-CH2- CH(CHs)-O-C(O)H instead of -(OCH2)2-OH.
Tables 34651 to 34804 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)2- O-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 34805 to 34958
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)2- O-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 34959 to 35112
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CHs)=CH-C(O)O-(CH2)2- O-(CH2)2-NHCHs instead of -(OCH2)2-OH.
Tables 35113 to 35266
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)O-(CH2)2- O-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 35267 to 35420 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)O-(CH2)2- O-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 35421 to 35574
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)O-(CH2)2- NH-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 35575 to 35728
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)O-(CH2)2- NH-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 35729 to 35882
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)O-(CH2)2- NH-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 35883 to 36036
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)O-(CH2)2- NH-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 36037 to 36190 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)O-(CH2)2- NH-(CH2)2-O-C(O)H instead of -(OCH2)2-OH. Tables 36191 to 36344
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)O-(CH2)2- N(CH3)-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 36345 to 36498
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)O-(CH2)2- N(CH3)-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 36499 to 36652
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)O-(CH2)2- N(CH3)-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 36653 to 36806 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)O-(CH2)2- N(CH3)-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 36807 to 36960
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C(CH3)=CH-C(O)O-(CH2)2- N(CH3)-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 36961 to 37114
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 37115 to 37268
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 37269 to 37422 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 37423 to 37576
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2- N(CHs)2 instead of -(OCH2)2-OH.
Tables 37577 to 37730
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-O- C(O)H instead of -(OCH2)2-OH.
Tables 37731 to 37884
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)3-OH instead of -(OCH2)2-OH.
Tables 37885 to 38038
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)3-NH2 instead of -(OCH2)2-OH.
Tables 38039 to 38192 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)3-NHCH3 instead of -(OCH2)2-OH. Tables 38193 to 38346
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)3- N(CHs)2 instead of -(OCH2)2-OH.
Tables 38347 to 38500
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)3-O- C(O)H instead of -(OCH2)2-OH.
Tables 38501 to 38654
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-CH(CHs)-CH2- OH instead of -(OCH2)2-OH.
Tables 38655 to 38808 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-CH(CHs)-CH2- NH2 instead of -(OCH2)2-OH.
Tables 38809 to 38962
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-CH(CHs)-CH2- NHCH3 instead of -(OCH2)2-OH.
Tables 38963 to 39116
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-CH(CHs)-CH2- N(CHs)2 instead of -(OCH2)2-OH.
Tables 39117 to 39270
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-CH(CHs)-CH2- 0-C(O)H instead of -(OCH2)2-OH.
Tables 39271 to 39424 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-CH2-CH(CHs)- OH instead of -(OCH2)2-OH.
Tables 39425 to 39578
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-CH2-CH(CHs)- NH2 instead of -(OCH2)2-OH.
Tables 30579 to 39732
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-CH2-CH(CHs)- NHCH3 instead of -(OCH2)2-OH.
Tables 39733 to 39886
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-CH2-CH(CHs)- N(CHs)2 instead of -(OCH2)2-OH.
Tables 39887 to 40040
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-CH2-CH(CHs)- 0-C(O)H instead of -(OCH2)2-OH.
Tables 40041 to 40194 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-O- (CH2)2-OH instead of -(OCH2)2-OH. Tables 40195 to 40348
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CHz)z-O- (CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 40349 to 40502
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-O- (CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 40503 to 40656
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-O- (CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 40657 to 40810 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-O- (CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 4081 1 to 40964
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-NH- (CH2)2-OH instead of -(OCH2)2-OH.
Tables 40965 to 41 118
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-NH- (CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 41 119 to 41272
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-NH- (CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 41273 to 41426 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-NH- (CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 41427 to 41580
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2-NH- (CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 41581 to 41734
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2- N(CH3)-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 41735 to 41888
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2- N(CH3)-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 41889 to 42042
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2- N(CH3)-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 42043 to 42196 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2- N(CH3)-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH. Tables 42197 to 42350
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)NH-(CH2)2- N(CH3)-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 42351 to 42504
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 42505 to 42658
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-(CH2)2- NH2 instead of -(OCH2)2-OH.
Tables 42659 to 42812 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-(CH2)2- NHCH3 instead of -(OCH2)2-OH.
Tables 42813 to 42966
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-(CH2)2- N(CHs)2 instead of -(OCH2)2-OH.
Tables 42967 to 43120
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-(CH2)2-O- C(O)H instead of -(OCH2)2-OH.
Tables 43121 to 43274
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)3-OH instead of -(OCH2)2-OH.
Tables 43275 to 43428 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)3- NH2 instead of -(OCH2)2-OH.
Tables 43429 to 43582
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)3- NHCH3 instead of -(OCH2)2-OH.
Tables 43583 to 43736
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)3- N(CHs)2 instead of -(OCH2)2-OH.
Tables 43737 to 43890
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-(CH2)3-O- C(O)H instead of -(OCH2)2-OH.
Tables 43891 to 44044
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-CH(CH3)- CH2-OH instead of -(OCH2)2-OH.
Tables 44045 to 44198 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-CH(CH3)- CH2-NH2 instead of -(OCH2)2-OH. Tables 44199 to 44352
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-CH(CHs)- CH2-NHCH3 instead of -(OCH2)2-OH.
Tables 44353 to 44506
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-CH(CHs)- CH2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 44507 to 44660
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-CH(CHs)- CH2-O-C(O)H instead of -(OCH2)2-OH.
Tables 44661 to 44814 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-CH2- CH(CHs)-OH instead of -(OCH2)2-OH.
Tables 44815 to 44968
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-CH2- CH(CHs)-NH2 instead of -(OCH2)2-OH.
Tables 44969 to 45122
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-CH2- CH(CHS)-NHCH3 instead of -(OCH2)2-OH.
Tables 45123 to 45276
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-CH2- CH(CHs)-N(CHs)2 instead of -(OCH2)2-OH.
Tables 45277 to 45430 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-CH2- CH(CHs)-O-C(O)H instead of -(OCH2)2-OH.
Tables 45431 to 45584
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-(CH2)2-O- (CH2)2-OH instead of -(OCH2)2-OH.
Tables 45585 to 45738
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-(CH2)2-O- (CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 45739 to 45892
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-(CH2)2-O- (CH2)2-NHCHs instead of -(OCH2)2-OH.
Tables 45893 to 46046
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-(CH2)2-O- (CH2)2-N(CHs)2 instead of -(OCH2)2-OH.
Tables 46047 to 46200 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CHs)-(CH2)2-O- (CH2)2-O-C(O)H instead of -(OCH2)2-OH. Tables 46201 to 46354
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)2- NH-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 46355 to 46508
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)2- NH-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 46509 to 46662
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)2- NH-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 46663 to 46816 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)2- NH-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 46817 to 46970
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)2- NH-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 46971 to 47124
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)2- N(CH3)-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 47125 to 47278
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)2- N(CH3)-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 47279 to 47432 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)2- N(CH3)-(CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 47433 to 47586
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)2- N(CH3)-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 47587 to 47740
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)N(CH3)-(CH2)2- N(CH3)-(CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 47741 to 47894
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-OH instead of -(OCH2)2-OH.
Tables 47895 to 48048
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 48049 to 48202 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-NHCH3 instead of -(OCH2)2-OH. Tables 48203 to 48356
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 48357 to 48510
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-O- C(O)H instead of -(OCH2)2-OH.
Tables 4851 1 to 48664
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)3-OH instead of -(OCH2)2-OH.
Tables 48665 to 48818 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is
Figure imgf000127_0001
instead of -(OCH2)2-OH.
Tables 48819 to 48972
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)3-NHCH3 instead of -(OCH2)2-OH.
Tables 48973 to 49126
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)3-N(CH3)2 instead of -(OCH2)2-OH.
Tables 49127 to 49280
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)3-O- C(O)H instead of -(OCH2)2-OH.
Tables 49281 to 49434 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-CH(CH3)-CH2- OH instead of -(OCH2)2-OH.
Tables 40435 to 49588
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-CH(CH3)-CH2- NH2 instead of -(OCH2)2-OH.
Tables 49589 to 49742
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-CH(CHs)-CH2- NHCH3 instead of -(OCH2)2-OH.
Tables 49743 to 49896
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-CH(CHs)-CH2- N(CHs)2 instead of -(OCH2)2-OH.
Tables 49897 to 50050
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-CH(CHs)-CH2- 0-C(O)H instead of -(OCH2)2-OH.
Tables 50051 to 50204 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-CH2-CH(CHs)- OH instead of -(OCH2)2-OH. Tables 50205 to 50358
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-CH2-CH(CHs)- NH2 instead of -(OCH2)2-OH.
Tables 50359 to 50512
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-CH2-CH(CHs)- NHCH3 instead of -(OCH2)2-OH.
Tables 50513 to 50666
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-CH2-CH(CHs)- N(CHs)2 instead of -(OCH2)2-OH.
Tables 50667 to 50820 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-CH2-CH(CHs)- 0-C(O)H instead of -(OCH2)2-OH.
Tables 50821 to 50974
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-O- (CH2)2-OH instead of -(OCH2)2-OH.
Tables 50975 to 51 128
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-O- (CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 51 129 to 51282
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-O- (CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 51283 to 51436 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-O- (CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 51437 to 51590
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-O- (CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 51591 to 51744
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-NH- (CH2)2-OH instead of -(OCH2)2-OH.
Tables 51745 to 51898
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-NH- (CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 51899 to 52052
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-NH- (CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 52053 to 52206 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-NH- (CH2)2-N(CH3)2 instead of -(OCH2)2-OH. Tables 52207 to 52360
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CHz)z-NH- (CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 52361 to 52514
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-N(CH3)- (CH2)2-OH instead of -(OCH2)2-OH.
Tables 52515 to 52668
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-N(CH3)- (CH2)2-NH2 instead of -(OCH2)2-OH.
Tables 52669 to 52822 Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-N(CH3)- (CH2)2-NHCH3 instead of -(OCH2)2-OH.
Tables 52823 to 52976
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-N(CH3)- (CH2)2-N(CH3)2 instead of -(OCH2)2-OH.
Tables 52977 to 53130
Compounds of the formula I. a in which the combination of R3, R4, L21 and L22 is as defined in any of Tables 1 to 154, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A and L1 is -C≡C-C(O)O-(CH2)2-N(CHs)- (CH2)2-O-C(O)H instead of -(OCH2)2-OH.
Tables 53131 to 106260
Compounds of the formula I. a in which the combination of R4, L1, L21 and L22 is as defined in any of Tables 1 to 53130, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A, and R3 is methyl.
Tables 106261 to 212520
Compounds of the formula I. a in which the combination of R3, R4, L1 and L21 is as defined in any of Tables 1 to 106260, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A, and L22 is fluorine.
Tables 212521 to 318780
Compounds of the formula I. a in which the combination of R3, R4, L1 and L22 is as defined in any of Tables 1 to 106260, the combination of R5 and R6 for a compound corresponds in each case to one row of Table A, and L21 is chlorine.
Tables 318781 to 637560
Compounds of the formula l.b in which the combination of R3, R4; L1, L21 and L22 is as defined in any of Tables 1 to 318780 and R1' for a compound corresponds in each case to one row of Table B.
Tables 637561 to 956340
Compounds of the formula l.c in which the combination of R3, R4; L1, L21 and L22 is as defined in any of Tables 1 to 318780 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Tables 956341 to 1275120
Compounds of the formula l.d in which the combination of R3, R4; L1, L21 and L22 is as defined in any of Tables 1 to 318780 and R1' for a compound corresponds in each case to one row of Table B.
Tables 1275121 to 1593900
Compounds of the formula l.e in which the combination of R3, R4; L1, L21 and L22 is as defined in any of Tables 1 to 318780 and the combination of R5 and R6 for a compound corresponds in each case to one row of Table A.
Tables 1593901 to 1912680
Compounds of the formula l.f in which the combination of R3, R4; L1, L21 and L22 is as defined in any of Tables 1 to 318780 and R1' for a compound corresponds in each case to one row of Table B. Table A
Figure imgf000133_0001
Figure imgf000134_0001
Figure imgf000135_0001
Figure imgf000136_0001
Figure imgf000137_0001
Figure imgf000138_0001
Figure imgf000139_0001
Figure imgf000140_0001
Figure imgf000141_0001
Figure imgf000142_0001
Figure imgf000143_0001
Figure imgf000144_0001
Figure imgf000145_0001
Figure imgf000146_0001
Figure imgf000147_0001
Figure imgf000148_0001
Figure imgf000149_0001
Figure imgf000150_0001
Table B
Figure imgf000151_0001
Figure imgf000151_0002
Figure imgf000152_0001
Figure imgf000152_0002
Figure imgf000153_0001
Figure imgf000153_0002
Figure imgf000154_0001
Figure imgf000154_0002
Figure imgf000155_0001
Figure imgf000155_0002
Figure imgf000156_0002
Figure imgf000156_0001
Figure imgf000157_0001
Figure imgf000157_0002
Figure imgf000158_0001
Figure imgf000158_0002
Figure imgf000159_0001
Figure imgf000159_0002
Figure imgf000160_0002
Figure imgf000160_0001
The compounds of the general formula I can be prepared by various routes analogously to processes, known per se, of the prior art for preparing substituted pyrazines.
In the below schemes and descriptions of the synthesis steps, the radicals marked with an asterisk (e.g. R1*, R2*, R3*, R4*) represent the radicals with the respective name without asterisk (i.e. R1, R2, R3, R4) as defined above or a suitable precursor for this group which can be easily transformed into the desired radical or the protected form of the respective radical (e.g. a boc-protected amino group, a benzyl-protected amino or hydroxyl group, a trialkylsilyl-protected hydroxyl group etc.). The radicals not marked with an asterisk have the meanings given above and if appropriate as specified in the description of the respective syntheses or in the schemes. As to formula numbers marked with an asterisk (e.g. I*), these represent a compound which falls under the scope of the respective generic formula but which can be further converted into another compound of the same generic formula. Scheme 1 :
Figure imgf000161_0001
In Scheme 1 , m is 1 , 2, 3 or 4, LG1 is a nucleophilically exchangeable group, such as halogen, for example fluorine, and v — is a carboaromatic or heteroaromatic radical as described above for R2, e.g. phenyl, benzyl or a five- or 6-membered heteroaromatic radical, but with the substituents of Scheme 1.
The reaction of Il with III is carried out, for example, in analogy to the method described in WO 2005/030775 and is advantageously carried out in the presence of strong bases. Suitable bases are, for example, alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, alkali metal carbonates, such as sodium carbonate or potassium carbonate, alkaline earth metal carbonates, such as calcium carbonate or magnesium carbonate, or alkali metal hydrides, such as lithium hydride or sodium hydride. The reaction can be carried out in the presence of a solvent. Suitable solvents are aprotic solvents, for example N,N-disubstituted amides, such as N,N-dimethylformamide, N, N- dimethylacetamide or N-methylpyrrolidone, sulfoxides, such as dimethyl sulfoxide, or ethers, such as diethyl ether, diisopropyl ether, tert-butyl ether, 1 ,2-dimethoxyethane, tetrahydrofuran, dioxane or anisole. The reaction is usually carried out at temperatures in the range of from 00C to the boiling point of the solvent.
If T in group L1 is OH or a primary or secondary amino group, it is advantageous to protect the hydroxyl group or the amino group. A suitable protective group for the hydroxyl group is, for example, the benzyl group which, if appropriate, carries a methoxy group in the 4-position of the phenyl ring. The protective group for the hydroxyl group can be removed, for example, by catalytic hydrogenolysis or with the aid of 2,3-dichloro-5,6-dicyano-1 ,4-benzoquinone (DDQ). A suitable protective group for primary and secondary amino groups is, for example, the tert-butoxycarbonyl group (Boc), which is usually removed using trifluoroacetic acid or p-toluenesulfonic acid.
Pyrazine derivatives of the formula Il are known from the literature and described, for example, in WO 2006/089060 and in the literature cited therein, the entire contents of which is incorporated herein by way of reference. Compounds Il not described in these publications can be prepared analogously to the processes described therein. Compounds of the formula III are generally commercially available or can be prepared by processes known from the literature.
Alternatively, compounds of the formula I in which L1 is a group attached via oxygen can be obtained according to the process described in Scheme 2.
Scheme 2:
Figure imgf000162_0001
In Scheme 2, m is 1 , 2, 3 or 4 and C ^D- ^ , is a carboaromatic or heteroaromatic radical as described above for R2, e.g. phenyl, benzyl or a five- or 6-membered heteroaromatic radical, but with the substituents of Scheme 2.
In a first step, the compound IV is reacted with a Lewis acid such as aluminum trichloride or iron(lll) chloride, which gives the hydroxylic compound V. The ether cleavage is usually carried out in an organic solvent, for example in an aromatic hydrocarbon, such as benzene, toluene or xylene. Group L1 is introduced by nucleophilic substitution of the hydroxyl group under basic conditions, as described in Scheme 1 .
Compounds of the formula IV are known from the publications mentioned above.
Compounds of the formula I in which Y1 in L1 is a group CRhR' can be prepared in an advantageous manner from compounds V. Initially, the hydroxyl compound V is reacted with trifluoromethanesulfonic anhydride, which gives a trifluoro- methanesulfonate Vl, and this is followed by reaction with an aminoalkylboronic acid. This route is shown in Scheme 3.
Scheme 3:
(CF3SOAO
Figure imgf000162_0003
Figure imgf000162_0002
(HO)2B-CRhR'-Y2-NRhR'
Figure imgf000163_0001
(I*)
In Scheme 3, m is 1 , 2, 3 or 4 and G ^-X ^ is a carboaromatic or heteroaromatic radical as described above for R2, e.g. phenyl, benzyl or a five- or 6-membered heteroaromatic radical, but with the substituents of Scheme 3.
Compounds of the formula I in which Y1 in L1 is a group -C(RV)=C(RW)-Y1-Y2-T can be prepared in an advantageous manner by reacting a compound Il where LG1 is a halogen atom and preferably a bromine atom in a Stille or Suzuki coupling reaction. The well-known Stille coupling is a versatile C-C bond forming reaction between stannanes and halides or pseudohalides catalyzed by palladium. Suitable reaction conditions are described for example in J. K. Stille et al., J. Org. Chem, 1990, 55, 3019- 3023. The Suzuki coupling is a palladium-catalysed cross coupling between organoboronic acid and halides. Suitable reaction conditions are described for example in Suzuki et al., Synth. Commun. 1981 , 11 , 513-519.
Compounds of the formula I in which Y1 in L1 is a group -C≡C-Y1-Y2-T can be prepared in an advantageous manner by reacting a compound Il where LG1 is a halogen atom and preferably a bromine atom in a Sonogashira coupling reaction. The Sonogashira coupling reaction is the coupling of terminal alkynes with aryl or vinyl halides and is performed with a palladium catalyst, a copper(l) cocatalyst, and an amine base.
Suitable reaction conditions are described for example in Sonogashira, K. et al.,
Tetrahedron Lett., 1975, 4467.
Compounds of the formula I in which L1 is a group attached via nitrogen can be prepared in an advantageous manner from precursors whose group ^- ^ carries an amino group which, if appropriate, can be obtained from the corresponding nitro- substituted compounds by reduction.
Compounds of the formula I in which R3 is cyano, d-Cs-alkoxy, d-Cs-alkylthio, Ci-Cs- haloalkoxy or d-Cs-haloalkylthio can be obtained in an advantageous manner by reacting compounds of the formula I in which R3 is halogen, preferably chlorine, with compounds M1-R3' (hereinbelow also compounds of the formula VII). Depending on the group R3' to be introduced, the compounds of the formula VII are inorganic cyanides, alkoxides, thiolates or haloalkoxylates. The reaction is advantageously carried out in an inert solvent. The cation M1 in formula VII is of little importance; for practical reasons preference is usually given to ammonium salts, tetraalkylammonium salts, such as tetramethylammonium salts or tetraethylammonium salts, or alkali metal or alkaline earth metal salts The salts VII can also be prepared in situ from the respective alcohol 5 or thiol H-R3' by reacting it with a strong inorganic base such as sodium hydride (Scheme 4).
Scheme 4:
(I*) + W-R* (I)
(R3 = Halogen) (VII) {R3=R3' = CN, CrC10-alkoxy, CrC10-alkylthio,
-| Q C1-C10-JIaIOaIkOXy, C^C^-haloalkylthio}
The reaction temperature is usually from 0 to 1200C, preferably from 10 to 400C [cf. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].
15 Suitable solvents include ethers, dioxane, diethyl ether, methyl tert-butyl ether and, preferably, tetrahydrofuran, halogenated hydrocarbons, such as dichloromethane or dichloroethane, aromatic hydrocarbons such as toluene, N,N-dimethylformamide, N- methylpyrrolidone and mixtures thereof.
20 Compounds of the formula I in which R3 is Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-C10- alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl and C3-Cio-halocycloalkyl can be prepared in an advantageous manner by reacting compounds of the formula I in which R3 is halogen with organometallic compounds R3a-M2 (VIII) in which R3a is Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-C10-
25 haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl or C3-C10- halocycloalkyl and M2 is lithium, magnesium or zinc. The reaction is preferably carried out in the presence of catalytic or, in particular, at least equimolar amounts of transition metal salts and/or transition metal compounds, in particular in the presence of Cu salts, such as Cu(I) halides and especially Cu(I) iodide. When the metal M2 is magnesium,
30 the coupling does not necessarily require a transition metal catalyst. In general, the reaction is carried out in an inert organic solvent, for example one of the ethers mentioned above, 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
35 purpose are in the range of from -100 to +100°C and especially in the range of from - 8O0C to +400C. Suitable processes are known, for example, from WO 03/004465 (Scheme 5) Scheme 5:
(I*) + IVP-R3' *- (I)
(R3 = Halogen) (VIM) {R3=R3' = CrC10-(halo)alkyl, C2-C10-(halo)alkenyl,
C2-C10-(halo)alkynyl, C3-C10-(halo)cycloalkyl}
Alternatively, compounds of the formula I in which R3 is Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl and C3-Cio-halocycloalkyl can be prepared in an advantageous manner by reacting compounds of the formula I in which R3 is halogen with organometallic compounds R3a- M3 (IX) in which R3a is Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl or C3-Cio-halocycloalkyl and M3 is Mg, B, Al, Si or Sn, in the presence of a palladium catalyst. When the metal M3 is magnesium, the coupling does not necessarily require a transition metal catalyst. The reaction can be carried out in analogy to the methods described in Hoornaert et. al., Tetrahedron, 1991 , 47, 9259-9268 and Tetrahedron Letters, 2004, 45, 1885-1888 and by Gribble and Li in "Palladium in Heterocyclic Chemistry", Pergamon Press, Amsterdam, 2000, page 41 1 (Scheme 6).
Scheme 6:
[Pd]
(I*) + M3-R3' (I)
(R3 = Halogen) (IX) {R3=R3' = c1-C10-(halo)alkyl, C2-C10-(halo)alkenyl, C2-C10-(halo)alkynyl, C3-C10-(halo)cycloalkyl}
Typical procedures for other palladium catalysed reactions of pyrazolones can be found in Tetrahedron, 2005, 61 , 3953-3962. For alkynyl compounds the Sonogashira reaction is most useful. For alkenyl substrates the Heck and Stille reactions are most useful. For alkyl and cycloalkyl the Kumada and Suzuki couplings are very useful.
Compounds of formula I where R4 is a heterocyclic ring optionally fused to phenyl or a heteroaromatic ring which is N-linked to the pyrazine moiety can be prepared by reacting a compound (X) where LG2 represents a nucleophilically exchangeable group, such as halogen (e.g. Cl, Br, I) or a sulfonyl group (e.g. methylsulfonl, trifluoromethylsulfonyl or tolylsulfonyl), with the desired monocyclic or fused heterocycle comprising an NH group (Xl) (Scheme 7).
Scheme 7:
Figure imgf000166_0001
(X) (Xl) (I)
H-N J
In scheme 7, ^^ represents a heterocycle as defined for R4 which comprises a group NH. LG2 represents a nucleophilically exchangeable group (leaving group) as defined above and R4 represents a heterocyclic ring as defined above which is bound via N.
The reaction is generally carried out in the presence of a base. Suitable bases for the reaction include inorganic bases, such as alkali or alkaline earth metal (such as lithium, sodium, potassium, cesium) hydrides, alkoxides, carbonates, phosphates and hydroxides, and organic bases, such as triethylamine, N,N-diisopropylethylamine and 1 ,8-diazabicyclo[5.4.0]undec-7-ene. Preferred acid acceptors are potassium carbonate and potassium hydroxide. A wide variety of solvents are suitable for the reaction, including, for example but are not limited to N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone, acetonitrile and acetone, as well as mixtures of these solvents. This reaction can be conducted between about 0 and 2000C, and preferably between about 20 and 800C.
Compounds of formula I where R4 is a heterocyclic ring optionally fused to phenyl or a heteroaromatic ring which is C-linked to the pyrazine moiety can be prepared by transition metal catalyzed reactions of compounds of (XII) wherein LG3 is halogen with compounds of formula (XIII). Transition metal catalyzed cross coupling reactions of halogenopyrazinones are known from the work of Hoornaert et al., Tetrahedron, 1991 , 47, 9259-9268 and Tetrahedron Letters, 2004, 45, 1885-1888. Reaction of various organometallic heterocycles of formula (XII) under palladium or nickel catalysis is possible. For the synthesis of organometallic heterocycles suitable for use in this reaction see Gribble and Li, "Palladium in Heterocyclic Chemistry", Pergamon Press, Amsterdam, 2000, page 41 1. This book also describes a wide variety of catalysts and reaction conditions suitable for carrying out the cross coupling reactions described in Scheme 8. When the metal is magnesium, the coupling does not necessarily require added transition metal catalyst.
Scheme 8:
Figure imgf000167_0001
(XII) (XIII) (I)
In scheme 8, Het represents a heterocycle as defined for R4 which is bound to M3 via a C atom. M3 is selected from Mg, B, Sn and Zn. LG2 represents a halogen atom and R4 in formula I represents a heterocyclic ring as defined above which is bound via C.
Alternatively, compounds of formula I where R4 is a heterocyclic ring optionally fused to phenyl or a heteroaromatic ring which is C-linked to the pyrazine moiety can be prepared by the conversion of a halogen substituted pyrazinone of formula (XII) into an organometallic derivative of formula (XIV) followed by a cross coupling reaction as shown in Scheme 9. Most preferably the organometallic pyrazinone is made by the reaction of a bimetallic reagent such as hexamethylditin with compounds of Formula (XII) under palladium catalysis. Other reagents such as pinacolatodiborane may also be used. The resulting tin compound of formula (XIV) can be transformed to compounds of formula I by palladium catalyzed coupling with haloheterocycles of
Formula (XV). Examples of the synthesis of heterocyclic tin compounds may be found in Majeed et al., Tetrahedron, 1989, 45, 993-1006.
Scheme 9:
Figure imgf000167_0002
In scheme 9, LG3 and LG4 are halogen atoms. Met is a metallating agent, in particular [Sn(CH3)3]2 or the corresponding diborane. M4 is a metal atom, in particular Sn or B. Het represents a heterocycle as defined for R4 which is bound to LG4 via a C atom. R4 in formula I represents a heterocyclic ring as defined above which is bound via C to the pyrazine moiety.
If the radical R4 in compounds of the formula I is a radical which can be introduced nucleophilically, the compound of the formula I is prepared by reacting the sulfone or the halide of the formula (X) with compounds R4-H. In general, the reaction is carried out under basic conditions. For practical reasons, the alkali metal, alkaline earth metal or ammonium salt of the compound R4-H can be employed directly. Alternatively, it is possible to add bases. This reaction is typically carried out under the conditions of a nucleophilic substitution; usually at from 0 to 2000C, preferably at from 10 to 1500C. If appropriate, it may be advantageous to carry out the reaction in the presence of a phase-transfer catalyst, for example 18-crown-6. The reaction is usually carried out in the presence of a dipolar aprotic solvent, such as an N,N-dialkylated carboxamide, for example N,N-dimethylformamide, a cyclic ether, for example tetrahydrofuran, or a carbonitrile, such as acetonitrile (cf. DE-A 39 01 084; Chimia, Vol. 50, pp. 525-530 (1996); Khim. Geterotsikl. Soedin, Vol. 12, pp. 1696-1697 (1998)).
In general, the compounds (X) and R4-H are employed in approximately stoichiometric amounts. However, it may be advantageous to use the nucleophile of the formula R4-H in excess, for example in excess of up to 10-fold, in particular up to 3-fold, based on the compound (X).
In general, the reaction is carried out in the presence of a base which may be employed in equimolar amounts or else in excess. Suitable bases are alkali metal carbonates and alkali metal bicarbonates, for example sodium carbonate and sodium bicarbonate, nitrogen bases, such as triethylamine, tributylamine and pyridine, alkali metal alkoxides, such as sodium methoxide or potassium tert-butoxide, alkali metal amides, such as sodium amide, or alkali metal hydrides, such as lithium hydride or sodium hydride.
Suitable solvents are halogenated hydrocarbons, ethers, such as diethyl ether, diiso- propyl ether, tert-butyl ether, 1 ,2-dimethoxyethane, dioxane, anisole and tetrahydrofuran, and also dimethyl sulfoxide, N,N-dialkylated carboxamides, such as dimethylformamide or dimethylacetamide, N-methylpyrrolidinone, nitriles, such as acetonitrile, and ketones, such as acetone. Particular preference is given to using ethanol, dichloromethane, acetonitrile, tetrahydrofuran, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone, and acetone. It is also possible to use mixtures of the solvents mentioned. For example, compounds of formula I where R4 is a hydrazone radical (-NRcN=CRaRb), oxime radical (-ON(=CRaRb)), hydrazine radical (-NRcNRaRb), amine radical (-NRaRb), hydroxylamine radical (-NRaRb; Rb = d-Ce-alkoxy; or -O-NRaRb) or CN can be synthesized in this way, i.e. by a reaction of an appropriate nucleophilic precursor of these groups, e.g. the corresponding hydrazone, oxime, hydrazine, amine or hydroxylamine or of a suitable salt thereof, e.g. NaCN or KCN, with a compound of formula (X) in the presence of a base. Potassium carbonate and tertiary amines such as triethylamine are preferred bases for hydrazones and hydrazines. Alkali hydrides such as sodium hydride are preferred bases for the oximes and hydroxylamines. Preferred solvents include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone, acetonitrile and acetone.
Compounds of the formula I in which R4 is cyano are useful intermediates for preparing further compounds of the formula I.
Compounds of the formula I in which R4 is a derivatized carboxylic acid radical such as C(=O)ORa, C(=O)NRaRb, C(=NORc)NRaRb, C(=O)NRa-NRdRb, C(=N-NRcRd)NRaRb, C(=O)RC, CRaRb-ORc, CRaRb-NRcRd can be obtained in an advantageous manner from the compounds of the formula I in which R4 is cyano by standard processes for derivatizing CN groups, where Ra, Rb, Rc and Rd have the meanings given above.
Compounds of the formula I in which R4 is -C(=O)NRaRb can be obtained from compounds of the formula I in which R4 is cyano by hydrolysis to the carboxylic acids (where R4 = -COOH) under acidic or basic conditions and amidation with amines HNRaRb.
By oximation with hydroxylamine or substituted hydroxylamines HbN-OR0 under basic conditions, the amides of the formula I (where R4 = -CONRaRb) afford the compounds of the formula I in which R4 is C(=NORc)NRaRb (cf. US 4,876,252). The substituted hydroxylamines can be used as free base or, preferably, in the form of their acid addition salts. For practical reasons, the halides, such as chlorides, or the sulfates are particularly suitable.
Compounds of the formula I in which R4 is -C(=N-NRcRd)NRaRb can be prepared in an advantageous manner from the corresponding cyano compounds Il by reaction with H2N-NRcRd to give the corresponding compounds of the formula I where R4 = C(=N-NRaRb)NH2. The compounds obtained in this manner can be mono- or dialkylated, which gives compounds of the formula I where R4 = -C(=N-NRcRd)NRaRb in which Ra and/or Rb are different from hydrogen. For suitable alkylation processes, reference is made to what was said above. Compounds of the formula I in which R4 is -C(=O)RC can be obtained from the corresponding cyano compounds I by reaction with Grignard reagents Rc-Mg-Hal in which Hal is a halogen atom, in particular chlorine or bromine, or with organolithium compounds Rc-Li. This reaction is advantageously carried out under the conditions known from J. Heterocycl. Chem. 1994, Vol. 31 (4), p. 1041. For example the reaction can be carried out at temperatures from -1000C to 25°C. Preferably the reaction is carried out in ether or tetrahydrofuran, beginning at -50 to -78°C and then allowing the reaction mixture to warm to 20 to 25°C.
The thus obtained ketones I (R4 = -C(=O)RC) can be converted into the corresponding oximes (R4 = -C(=W)RC; W = NRd; Rd = alkoxy) or hydrazones (R4 = -C(=W)RC; W = NNRdRe) by reacting the ketone with compounds NH2-NRd (Rd = alkoxy) or IMH2- NRdRe)Rc in a variety of solvents and temperatures. Preferred solvents for this transformation include lower alcohols, tetrahydrofuran and dioxane optionally mixed with water. Most preferred is the use of ethanol. The reaction can be carried out at temperatures from 0 to 1200C and is most commonly done at the reflux temperature of the solvent used.
Compounds of the formula I in which R4 is -CRaRb-ORc can be obtained from the corresponding ketones in which R4 is -C(=O)RC by reaction with Grignard reagents
RaRb-Mg-Hal* in which Hal* is a halogen atom, in particular chlorine or bromine, and, if appropriate, subsequent alkylation.
Compounds of the formula I in which R4 is -CH2-ORc can be obtained from the corresponding ketones in which R4 is -C(=O)RC by reaction with a metal hydride, for example lithium aluminum hydride, and, if appropriate, subsequent alkylation.
Compounds of the formula I in which R4 is -C(=O)ORa can be obtained by esterification of the compounds Il (R4 = -COOH) under acidic or basic conditions.
Compounds of the formula I in which R4 is -C(=S)NRaRb can be obtained by reacting compounds of the formula I in which R4 is CN with hydrogen sulfide or other sulfide sources and, if appropriate, subsequent mono- or dialkylation at the amide nitrogen. This reaction may be carried out in a variety of solvents and temperatures. Reaction in mixtures of lower alcohols and water is preferred. For a convenient procedure using ammonium as the sulfide source see Bagley et al., Synlett, 2004, 2615-2617.
Compounds of the formula I in which R4 is -C(=O)NRaRb can further be obtained by reacting a compound (XII) (i.e. a compound I where R4 is halogen) with a compound azole-CH2-CN which has previously been treated with a strong base such as sodium hexamethyldisilazide, sodium hydride, or 1 ,8-diazabicyclo-[5.4.0]undec-7-ene, followed by reaction with an oxidizing agent, such as peracetic acid, tert-butyl hydroperoxide, bleach, m-chloroperbenzoic acid or nickel peroxide, and then reacting the oxidation product with an amine NHRaRb. Reaction temperatures of between -200C and 800C are preferred with a temperature of 20 to 30°C being most preferred. A variety of solvents may be employed with tetrahydrofuran being preferred. For a survey of the use of this amide formation technique with a variety of heterocyclic halides, see Zhang, Synlett, 2004, 2323- 2326.
Compounds of the formula I in which R1 is NR5R6 or N=CR7R8 can be prepared as is shown in scheme 10.
Scheme 10:
Figure imgf000171_0001
(XV) (XVI) (l-a)
Figure imgf000171_0002
reducing
(XVII) agent
Figure imgf000171_0003
Figure imgf000171_0004
(l-b) (l-c)
A compound of formula (XV) can be converted to a compound of formula (XVI) by treatment with strong acid. A variety of acids may be successfully employed. Trifluoroacetic acid is a preferred acid for this transformation. The reaction is generally carried out at about 20 to 300C in an inert solvent such as dichloromethane. A variety of reagents can convert compounds of formula (XVI) to compounds of formula (l-a). Many amination reagents are known in the literature and have been discussed in some detail in Vedejs, Org. Lett., 2003, 7, 4187-4190 and references cited within. A preferred reagent is O-di(p-methoxyphenyl)phosphinylhydroxylamine. The presence of a base such as sodium hydride is preferred. Reaction of compounds of formula (l-a) with aldehydes and ketones of formula (XVII) give compounds of formula (l-b). The reaction can be carried in the presence of an acid with or without a solvent. Appropriate solvents include tetrahydrofuran, dichloromethane or lower alcohols. Compounds of formula (l-b) can be reduced to compounds of formula (l-c) by standard reduction techniques. Generally these reactions are conducted by reaction of a boron-based reducing agent such as sodium borohydride or sodium triacetoxyborohydride with the compound of formula (l-b) in a solvent such as lower alcohols or tetrahydrofuran. Other reduction techniques known to those skilled in the art may also be employed. A compendium of methods and techniques of reduction of imine type bonds can be found in Organic Reactions, (New York) 2002, 59, 1- 714.
The pyrazine scaffold can be synthesized by various methods, for example as described in WO 2006/089060.
For example, compounds of formula I in which A is O and R3 and R4 are halogen can be prepared by the reaction of cyanoamines of formula (XVIII) with oxalyl halides as shown in Scheme 11. The reaction is carried out with an excess of an oxalyl halide. The reaction is best carried out in an inert solvent such as 1 ,2-dichlorobenzene, toluene, chlorobenzene or xylenes at elevated temperatures between about 60 and 1500C. In some cases, the reaction can be carried out at lower temperatures from about 20 to about 600C if N,N-dimethylformamide is added to the mixture after the addition of the oxalyl halide. The addition of a halide source such as tetraalkylammonium halides or trialkylammonium halides can sometimes also result in higher yields of product and/or lower reaction temperatures. This type of cyclization can be found in J Heterocyclic Chemistry, 1983, 20, 919-923, Bull Soc. CMm. BeIg. 1994, 103, 583-589, J. Med. Chem., 2005, 48, 1910-1918, and Tetrahedron, 2004, 60, 11597-1 1612, and references cited therein.
Scheme 11 :
Figure imgf000172_0001
(XVIII) (I)
The compounds (XVIII) can be made by a Strecker synthesis, as shown in scheme 12. This well known reaction involves the reaction of an aldehyde of formula (XIX) and an amine of formula (XX) with a cyanide source. The free aldehyde of formula (XIX) may be used or it can also be treated with sodium bisulfite prior to the addition to form a bisulfite adduct. The amine of formula (XX) may be in the form of a free base or as an acid addition salt. A variety of solvents and cyanide sources can be employed. For cases in which R1 is aryl the presence of a Lewis acid such as indium(lll) chloride can be advantageous (for example, see, Rami et. at, Tetrahedron, 2002, 58, 2529-2532 for typical conditions). This reaction has been the subject of a number of reviews. For conditions and variations of this reaction see the following reference and references cited therein: D. T. Mowry, Chemical Reviews, 1948, 42, 236, H. Groeger, Chemical Reviews, 2003, 103, 2795-2827, and M. North in "Comprehensive Organic Functional Group Transformations" A. R. Katritsky, O. Meth-Cohn and C. W. Rees Editors., Volume 3, 615-617; Pergamon, Oxford, 1995.
Scheme 12:
R2*-CHO + R1*NH2 cvanicle , source
Figure imgf000173_0001
(XIX) (XX) (XVIII)
Compounds of formula I in which A is NH and R4 is a nitrile can be synthesized from compounds of enamines of formula (XXI) by a two-step procedure as shown in scheme 13. The enamines are reacted with [[[(4-methylphenyl)sulfonyl]oxy]imino]propane- dinitrile in the presence of a base such as pyridine or triethylamine in a variety of solvents to afford compounds of formula (XXII). Preferred solvents include chloroform, dichloromethane and N,N-dimethylformamide. In a second step the compounds of formula (XXII) are reacted with an amine of formula (XXIII) to afford the desired compounds of Formula I. Examples of these procedures can be found in Lang et al., HeIv. Chem. Acta., 1986, 69, 1025-1033.
Scheme 13:
Figure imgf000173_0002
(XXI) (XXII) (I)
The synthesis of enamines of formula (XXI) is well known in the art. For a review of preparative methods see for example Hickmott, et al., Tetrahedron, 1982, 55, 1975- 2050 and Tetrahedron, 1982, 38, 3363-3446. Compounds of formula I in which A is NH and R4 is CONH2 can be synthesized from compounds of Formula I in wherein A is NH and R4 is a nitrile by acidic hydrolysis Reagents such as trifluoroacetic acid and trifluoroacetic acid/sulfuric acid mixtures can be employed. This reaction can be conducted between about 0 and 2000C, and preferably between about 20 and 8O0C.
The reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of colorless or slightly brownish viscous oils which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.
If individual compounds I cannot be obtained by the routes described above, they can be prepared by derivatization of other compounds I.
If the synthesis yields mixtures of isomers, a separation is generally however not required since in some cases the individual isomers can be interconverted during work- up for use or during application (for example under the action of light, acids or bases). Such conversions may also take place after application, for example, in the case of the treatment of plants, in the treated plants, or in the harmful fungus to be controlled.
The compounds I are suitable for use as fungicides. They have excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Basidiomycetes and Peronosporomycetes (syn. Oomycetes). Some of them are systemically active and can be used in crop protection as foliar fungicides, as fungicides for seed dressing and as soil fungicides.
They are particularly important for the control of a large number of fungi on various crop plants, such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soybeans, coffee, sugarcane, grapevines, fruit and ornamental plants and vegetables, such as cucumbers, beans, tomatoes, potatoes and cucurbits, and also on the seeds of these plants.
Moreover, they are useful for controlling Botryospheria species, Cylindrocarpon species, Eutypa lata, Neonectria liriodendri and Stereum hirsutum which inter alia attack the wood and roots of grapevines.
The compounds I are particularly suitable for controlling the plant diseases mentioned below: The compounds I are suitable for controlling Alternaria species on vegetables, rapeseed, sugarbeet, fruit, rice, soybeans and potatoes such as, for example, A. solani or A. alternata on potatoes and tomatoes and A. ssp. on wheat. The compounds I are suitable for controlling Aphanomyces species on sugarbeet and vegetables.
The compounds I are suitable for controlling Ascochyta species on cereals and vegetables, for example, Ascochyta tritici an wheat.
The compounds I are suitable for controlling Bipolaris and Drechslera species on corn, cereals, rice and lawns, such as, for example, D. maydis on corn.
The compounds I are suitable for controlling Blumeria graminis (powdery mildew) on cereals (for example wheat or barley).
The compounds I are suitable for controlling Botrytis cinerea (gray mold) on strawberries, vegetables, flowers grapevines and wheat. The compounds I are suitable for controlling Bremia lactucae on lettuce.
The compounds I are suitable for controlling Cercospora species on corn, soybeans, rice and sugarbeet, for example Cercospora sojina or Cercospora kikuchii on soybeans.
The compounds I are suitable for controlling Cladosporium herbarum on wheat. The compounds I are suitable for controlling Cochliobolus species on corn, cereals, rice, such as, for example, Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice.
The compounds I are suitable for controlling Colletotricum species on soybeans and cotton, for example Colletotricum truncatum (antracnosis) on soybeans. The compounds I are suitable for controlling Corynespora cassiicola on soybeans.
The compounds I are suitable for controlling Dematophora necatrix on soybeans.
The compounds I are suitable for controlling Diaporthe phaseolorum on soybeans.
The compounds I are suitable for controlling Drechslera species, Pyrenophora species on corn, cereals, rice and lawns, such as, for example, D. teres on barley or D. tritici- repentis on wheat.
The compounds I are suitable for controlling Esca on grapevines, caused by
Phaeoacremonium chlamydosporium, Ph. Aleophilum, and Formitipora punctata (syn.
Phellinus punctatus).
The compounds I are suitable for controlling Elsinoe ampelina on grapevines. The compounds I are suitable for controlling Epicoccum spp. on wheat.
The compounds I are suitable for controlling Exserohilum species on corn.
The compounds I are suitable for controlling Erysiphe cichoracearum and
Sphaerotheca fuliginea on cucumbers.
The compounds I are suitable for controlling Fusarium and Verticillium species on various plants, such as, for example, F. graminearum or F. culmorum on cereals (e.g. wheat or barley) or F. oxysporum on a large number of plants, such as, for example, tomatoes or F. solani on soybeans.
The compounds I are suitable for controlling Gaeumanomyces graminis on cereals
(e.g. wheat or barley). The compounds I are suitable for controlling Gibberella species on cereals and rice (for example Gibberella fujikuroi on rice).
The compounds I are suitable for controlling Glomerella cingulata on grapevines and other plants.
The compounds I are suitable for controlling Grainstaining complex on rice. The compounds I are suitable for controlling Guignardia budwelli on grapevines.
The compounds I are suitable for controlling Helminthosporium species on corn and rice.
The compounds I are suitable for controlling lsariopsis clavispora on grapevines.
The compounds I are suitable for controlling Macrophomina phasolina on soybeans. The compounds I are suitable for controlling Michrodochium nivale on cereals (e.g. on wheat or barley).
The compounds I are suitable for controlling Microsphera diffusa on soybeans.
The compounds I are suitable for controlling Mycosphaerella species on cereals, bananas and peanuts, such as, for example, M. graminicola on wheat or M. fijiensis on bananas.
The compounds I are suitable for controlling Peronospora species on cabbage and bulbous plants, such as, for example, P. brassicae on cabbage or P. destructor on onions or P. manshurica on soybeans.
The compounds I are suitable for controlling Phakopsara pachyrhizi and Phakopsara meibomiae on soybeans.
The compounds I are suitable for controlling Phomopsis species on soybeans and sunflowers.
The compounds I are suitable for controlling Phialophora gregata on soybeans.
The compounds I are suitable for controlling Phomopsis species on sunflowers, grapevines and soybeans, for example P. viticola on grapevines or P. phaseoli on soybeans.
The compounds I are suitable for controlling Phytophthora infestans on potatoes and tomatoes.
The compounds I are suitable for controlling Phytophthora species on various plants, such as, for example, P. capsici on bell peppers, P. megasperma on soybeans, P. infestans on tomatoes and potatoes.
The compounds I are suitable for controlling Plasmopara viticola on grapevines.
The compounds I are suitable for controlling Podosphaera leucotricha on apples.
The compounds I are suitable for controlling Pseudocercosporella herpotrichoides on cereals (e.g. wheat or barley).
The compounds I are suitable for controlling Pseudoperonospora on various plants, such as, for example, P. cubensis on cucumbers or P. humili on hops. The compounds I are suitable for controlling Pseudopezicula tracheiphilai on grapevines.
The compounds I are suitable for controlling Puccinia species on various plants, such as, for example, P. triticina, P. striformins, P. hordei or P. graminis on cereals (e.g. wheat or barley), or P. asparagi on asparagus.
The compounds I are suitable for controlling Pyrenophora tritici-repentis on wheat and
Pyrenophora teres on barley.
The compounds I are suitable for controlling Pyricularia oryzae, Corticium sasakii,
Sarocladium oryzae, S. attenuatum, Entyloma oryzae on rice. The compounds I are suitable for controlling Pyricularia grisea on lawns and cereals.
The compounds I are suitable for controlling Pythium spp. on lawns, rice, corn, cotton, rapeseed, sunflowers, sugarbeet, vegetables and other plants, such as, for example,
P.ultiumum on various plants, P. aphanidermatum.
The compounds I are suitable for controlling Ramularia collo-cygni (Ramularia/physiological leaf spots) on barley.
The compounds I are suitable for controlling Rhizoctonia species on cotton, rice, potatoes, lawns, corn, rapeseed, sugarbeet, vegetables and on various plants, such as, for example, R. solani on beet, soybeans and various plants and R. cerealis on wheat and barley. The compounds I are suitable for controlling Rhynchosporium secalis on barley, rye and triticale.
The compounds I are suitable for controlling Sclerotinia species on rapeseed and sunflowers, for example Sclerotinia sclerotiorum or Sclerotinia rolfsii on soybeans.
The compounds I are suitable for controlling Septoria glycines on soybeans. The compounds I are suitable for controlling Septoria tritici and Stagonospora nodorum on wheat.
The compounds I are suitable for controlling Erysiphe (syn. Uncinula) necator on grapevines.
The compounds I are suitable for controlling Setospaeria species on corn and lawns. The compounds I are suitable for controlling Sphacelotheca reilinia on corn.
The compounds I are suitable for controlling Thievaliopsis species on soybeans and cotton.
The compounds I are suitable for controlling Tilletia species on cereals.
The compounds I are suitable for controlling Typhula incarnata on wheat and barley. The compounds I are suitable for controlling Ustilago species on cereals, corn and sugarcane, such as, for example, U. maydis on corn.
The compounds I are suitable for controlling Venturia species (scab) on apples and pears, such as, for example, V. inaequalis on apples.
In particular, compounds I are useful for controlling phytopathogenic fungi from the class of the Peronosporomycetes (syn. Oomycetes), such as Perenospora species, Phytophthora species, Plasmopara viticola, Pseudoperonospora species and Phythium species.
In addition, the compounds according to the invention can also be used in crops which, owing to breeding including genetic engineering, are tolerant to attack by insects or fungi.
The compounds I are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products. In the protection of wood, particular attention is paid to the following harmful fungi: Ascomycetes, such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes, such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes, such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes, such as Mucor spp., additionally in the protection of materials the following yeasts: Candida spp. and Saccharomyces cerevisae.
The compounds according to the invention and/or their agriculturally acceptable salts are employed by treating the fungi or the plants, seeds or materials to be protected against fungal attack or the soil with a fungicidally effective amount of the active compounds. Application can be both before and after the infection of the materials, plants or seeds by the fungi.
Accordingly, the invention furthermore provides a method for controlling phytopathogenic fungi wherein the fungi or the materials, plants, the soil or seed to be protected against fungal attack are/is treated with an effective amount of at least one compound I according to the invention and/or an agriculturally acceptable salt thereof.
The invention furthermore provides a composition for controlling phytopathogenic fungi, which composition comprises at least one compound according to the invention and/or an agriculturally acceptable salt thereof and at least one solid or liquid carrier.
The fungicidal compositions generally comprise between 0.1 and 95% by weight, preferably between 0.5 and 90% by weight, of active compound.
When employed in crop protection, the application rates are, depending on the kind of effect desired, between 0.01 and 2.0 kg of active compound per ha.
In seed treatment, the amounts of active compound required are generally from 1 to 1000 g/100 kg of seed, preferably from 5 to 100 g/100 kg of seed.
When used in the protection of materials or stored products, the active compound application rates depend on the kind of application area and on the desired effect. Amounts typically applied in the protection of materials are, for example, from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active compound per cubic meter of treated material.
The compounds of the formula I can be present in different crystal modifications which may differ in their biological activity. They are likewise subject matter of the present invention.
The compounds I can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the particular purpose; in each case, it should ensure a fine and uniform distribution of the compound according to the invention.
The formulations are prepared in a known manner, for example by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants. Solvents/auxiliaries suitable for this purpose are essentially:
water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used, carriers such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example finely divided silica, silicates); emulsifiers such as nonionogenic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquors and methylcellulose.
The compounds of the invention can be formulated in solid or liquid form. Depending on the form, the formulations can contain additives and/or carriers as they are usual in crop protection conpositions or in compositions for material protection. Additives comprise in particular conventional surface-active agents and other additives and carriers usually used in compositions for crop or material protection which can be liquid or solid. Surface-active agents comprise in particular surfactants, in particular surfactants having wetting agent properties. Other additives comprise in particular thickeners, defoamers, preservatives, antifreezing agents, stabilizers, anticaking agents or gushing agents and buffers. Principally useful conventional surface-active agents are anionic, nonionic and amphoteric surfactants, including polymer surfactants, where the molecular weight of the surfactant typically is not higher than 2000, in particular not higher than 1000 Daltons (number average molecular weight).
Anionic surfactants are for example carboxylates, in particular the alkaline metal, alkaline earth metal and ammonium salts of fatty acids e.g. potassium stearate, which are usually termed soaps; acylglutamates; sarkosinates, e.g. sodium lauroylsarkosinate; taurates; methylcelluloses; alkylphosphates, in particular the mono- and dialkylates of phosphoric acid; sulfates, in particular alkyl sulfates and alkyl ethersulfates; sulfonates, further alkyl- and alkylarylsulfonates, in particular the alkaline metal, alkaline earth metal and ammonium salts of arylsulfonic acids and alkyl- substituted aryl sulfonic acids, akylbenzenesulfonic acids, such as lignin- and phenolsulfonic acids, naphthalene- and dibutylnaphthalenesulfonic acids, or dodecylbenzenesulfonat.es, alkylnaphthalenesulfonat.es, alkylmethylestersulfonat.es, condensates of sulfonated naphthalene or derivatives thereof with formaldehyde, condensates of naphthalene sulfonic acid, phenol and/or phenolsulfonic acids with formaldehyde or with formaldehyde and urea, mono- oder dialkylsuccinicester sulfonates; and protein hydrolysates and lignosulfite waste liquors. The above sulfonic acids are advantageously used in form of their neutral or optionally basic salts.
The nonionic surfactants include, for example:
- fatty alcohol alkoxylates and oxoalcohol alkoxylates, in particular ethoxylates and propoxylates having degrees of alkoxylation of usually from 2 to 100 and in particular from 3 to 50, for example alkoxylates of Cs-Cso-alkanols or alk(adi)enols, for example of isotridecyl alcohol, lauryl alcohol, oleyl alcohol or stearyl alcohol, and their Ci-C4-alkyl ethers and Ci-C4-alkyl esters, for example their acetates; alkoxylated animal and/or vegetable fats and/or oils, for example corn oil ethoxylates, castor oil ethoxylates, tallow fat ethoxylates, glycerol esters, such as, for example, glycerol monostearate, alkylphenol alkoxylates, such as, for example, ethoxylated isooctylphenol, octylphenol or nonylphenol, tributylphenol polyoxyethylene ether, fatty amine alkoxylates, fatty acid amide alkoxylates and fatty acid diethanol- amide alkoxylates, in particular their ethoxylates, sugar surfactants, sorbitol esters, such as, for example, sorbitan fatty acid esters (sorbitan monooleate, sorbitan tristearate), polyoxyethylene sorbitan fatty acid esters, alkyl polyglycosides, N-alkylgluconamides, alkyl methyl sulfoxides, alkyldimethylphosphine oxides, such as, for example, tetradecyldimethyl- phosphine oxide.
The amphoteric surfactants include, for example, sulfobetaines, carboxybetaines and alkyldimethylamine oxides, for example tetradecyldimethylamine oxide.
Other surfactants which may be mentioned here by way of example are perfluoro surfactants, silicone surfactants, phospholipids, such as, for example, lecithin or chemically modified lecithins, amino acid surfactants, for example N-lauroylglutamate.
Suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.
Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substance(s) and, if present, further active substances, with at least one solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to at least one solid carrier. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
For seed treatment, the formulations were diluted twice to tenfold. This gives ready-to- use preparations having active compound concentrations of from 0.01 to 60% by weight, preferably of from 0.1 to 40% by weight.
The following are examples of formulations:
1. Products for dilution with water A Water-soluble concentrates (SL, LS)
10 parts by weight of the active compound(s) are dissolved with 90 parts by weight of water or with a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound dissolves upon dilution with water. This gives a formulation having an active compound content of 10% by weight.
B Dispersible concentrates (DC)
20 parts by weight of the active compound(s) are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion. The active compound content of the concentrate is 20% by weight.
C Emulsifiable concentrates (EC) 15 parts by weight of the active compound(s) are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The formulation has an active compound content of 15% by weight.
D Emulsions (EW, EO, ES)
25 parts by weight of the active compound(s) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is added to 30 parts by weight of water by means of an emulsifying machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The formulation has an active compound content of 25% by weight.
E Suspensions (SC, OD, FS)
In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active compound content in the formulation is 20% by weight.
F Water-dispersible granules and water-soluble granules (WG, SG)
50 parts by weight of the active compound(s) are ground finely with addition of 50 parts by weight of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound. The formulation has an active compound content of 50% by weight. G Water-dispersible powders and water-soluble powders (WP, SP, SS, WS) 75 parts by weight of the active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound. The active compound content of the formulation is 75% by weight.
H Gel formulations (GF)
20 parts by weight of the active compound(s), 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or an organic solvent are ground in a ball mill to give a fine suspension. Dilution with water gives a stable suspension with an active compound content of 20% by weight.
2. Products to be applied undiluted
I Dusts (DP, DS)
5 parts by weight of the active compound(s) are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product with an active compound content of 5% by weight.
J Granules (GR, FG, GG, MG)
0.5 part by weight of the active compound(s) is ground finely and associated with 99.5 parts by weight of carriers. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules with an active compound content of 0.5% by weight to be applied undiluted.
K ULV solutions (UL)
10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product with an active compound content of 10% by weight to be applied undiluted.
Water-soluble concentrates (LS), suspensions (FS), dusts (DS), water-dispersible and water-soluble powders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) and gel formulations (GF) are usually used for the treatment of seed. These formulations can be applied to the seed in undiluted or, preferably, diluted form. The application can be carried out before sowing.
The active compounds can be used 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, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; the intention is to ensure in each case the finest possible distribution of the active compounds according to the invention.
Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1 %.
The active compounds may also be used successfully in the ultra-low-volume process (ULV), by which it is possible to apply formulations comprising over 95% by weight of active compound, or even to apply the active compound without additives.
Various types of oils, wetters, adjuvants, herbicides, fungicides, other pesticides, or bactericides may be added to the active compounds, if appropriate not until immediately prior to use (tank mix). These compositions can be admixed with the compositions according to the invention in a weight ratio of from 1 :100 to 100:1 , preferably from 1 :10 to 10:1.
The following are particularly suitable as adjuvants in this context: organically modified polysiloxanes, for example Break Thru S 240®; alcohol alkoxylates, for example Atplus 245®, Atplus MBA 1303®, Plurafac LF 300® and Lutensol ON 30®; EO-PO block polymers, for example Pluronic RPE 2035® and Genapol B®; alcohol ethoxylates, for example Lutensol XP 80®; and sodium dioctylsulfosuccinate, for example Leophen RA®.
The compounds according to the invention in the application form as fungicides can also be present together with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers. When mixing the compounds according to the invention or the compositions comprising them with one or more further active compounds, in particular fungicides, it is in many cases possible, for example, to widen the activity spectrum or to prevent the development of resistance. In many cases, synergistic effects are obtained.
The present invention furthermore provides a combination of at least one compound according to the invention and/or an agriculturally acceptable salt thereof and at least one further fungicidal, insecticidal, herbicidal and/or growth-regulating active compound.
The following list of fungicides with which the compounds according to the invention can be applied together is meant to illustrate the possible combinations, but not to limit them:
strobilurins azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyribencarb, trifloxystrobin, 2-(2-(6-(3-chloro-2-methyl-phenoxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)-
2-methoxyimino- N-methyl-acetamide, methyl (2-chloro-5-[1-(3- methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1 -(6-methylpyridin-
2-ylmethoxyimino)ethyl]benzyl)carbamate, methyl 2-(ortho-(2,5-dimethylphenyl- oxymethylene)phenyl)-3-methoxyacrylate, methyl 3-methoxy-2-(2-(N-(4-methoxy- phenyl)-cyclopropancarboximidoylsulfanylmethyl)-phenyl) acrylate;
carboxamides
- carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, furametpyr, isotianil, kiralaxyl, mepronil, metalaxyl, ofurace, oxadixyl, oxycarboxin, penthiopyrad, tecloftalam, thifluzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxanilide, 2-chloro-N-(1 ,1 ,3-trimethyl-indan-4-yl)- nicotinamide, N-(3',4'-dichloro-5-fluoro-biphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H- pyrazol-4-carboxamide, N-(2-(1 ,3-dimethyl-butyl)-phenyl)-1 ,3,3-trimethyl-5-fluoro- 1 H-pyrazol-4-carboxamide, N-(4'-chloro-3',5-difluoro-biphenyl-2-yl)-3-difluoromethyl-
1 -methyl-1 H-pyrazol-4-carboxamide, N-(4'-chloro-3',5-difluoro-biphenyl-2-yl)-3- trifluoromethyl-1 -methyl-1 H-pyrazol-4-carboxamide, N-(3',4'-dichloro-5-fluoro- biphenyl-2-yl)-3-trifluoromethyl-1 -methyl-1 H-pyrazol-4-carboxamide, N-(3',5-difluoro- 4'-methyl-biphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazol-4-carboxamide, N-(3',5-difluoro-4'-methyl-biphenyl-2-yl)-3-trifluoromethyl-1 -methyl-1 H-pyrazol-4- carboxamide, N-(2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1 -methyl-1 H-pyrazol- 4-carboxamide, N-(cis-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1 -methyl-1 H- pyrazol-4-carboxamide, N-(trans-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1- methyl-1 H-pyrazol-4-carboxamide, N-(4'-bromobiphenyl-2-yl)-4-difluoromethyl-2- methylthiazole-5-carboxamide, N-(4'-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-
2-methylthiazole-5-carboxamide, N-(4'-chloro-3'-fluorobiphenyl-2-yl)-4-difluoro- methyl-2-methylthiazole-5-carboxamide, N-(3',4'-dichloro-4-fluorobiphenyl-2-yl)-3- difluoromethyl-1-methylpyrazole-4-carboxamide, N-(3',4'-dichloro-5-flurobiphenyl-2- yl)-3-difluoromethyl-1 -methyl pyrazole-4-carboxamide, N-(2-cyanophenyl)-3,4- dichloroisothiazole-5-carboxamide;
- carboxylic acid morpholides: dimethomorph, flumorph;
- benzamides: flumetover, fluopicolide (picobenzamid), fluopyram, zoxamide, N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxy benzamide;
- other carboxamides: carpropamid, diclocymet, mandipropamid, oxytetracyclin, silthiofam, N-(6-methoxy-pyridin-3-yl)cyclopropanecarboxamide, N-(2-(4-[3-(4- chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl)ethyl)-2-methanesulfonylamino-3- methylbutyramide, N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3- methoxyphenyl)ethyl)-2-ethanesulfonylamino-3-methylbutyramide;
azoles
- triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimenol, triadimefon, triticonazole, uniconazol, 1-(4-chloro-phenyl)-2-(1 H-[1 ,2,4]triazol-1- yl)cycloheptanol;
- imidazoles: cyazofamid, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole;
- benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;
- others: ethaboxam, etridiazole, hymexazole, 1-(4-chloro-phenyl)-1-(propyn-2-yloxy)- 3-(4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl)-propan-2-one;
nitrogenous heterocyclyl compounds
- pyridines: fluazinam, pyrifenox, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]- pyridine, 2,3,5,6-tetrachloro-4-methanesulfonyl pyridine, 3,4,5-trichloropyridine-2,6- dicarbonitrile, N-(1 -(δ-bromo-S-chloro-pyridin^-y^-ethyQ^^-dichloronicotinamide,
N-((5-bromo-3-chloro-pyridin-2-yl)-methyl)-2,4-dichloro-nicotinamide;
- pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, fenarimol, mepanipyrim, nitrapyrin, nuarimol, pyrimethanil;
- piperazines: triforine: - pyrroles: fludioxonil, fenpiclonil;
- morpholines: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph;
- dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;
- others: acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, captafol, chinomethionat, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat methylsulphate, famoxadone, fenamidone, fenoxanil, fenpropidin, folpet, famoxadone, fenamidone, octhilinone, oxolin acid, piperalin, probenazole, proquinazid, pyroquilon, quinoxyfen, triazoxide, tricyclazole, triforine, 5-chloro-7-(4- methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine, 2-butoxy-6-iodo-3-propylchromene-4-one, N, N-dimethyl-3-(3-bromo-6-fluoro-2- methylindole-1 -sulfonyl)-[1 ,2,4]triazole-1 -sulfonamide; carbamates and dithiocarbamates
- thio and dithiocarbamates: ferbam, mancozeb, maneb, metiram, metam, methasulphocarb, propineb, thiram, zineb, ziram;
- carbamates: diethofencarb, flubenthiavalicarb, benthiavalicarb, iprovalicarb, propamocarb, propamocarb hydrochloride, valiphenal, methyl 3-(4-chlorophenyl)-3-
(2-isopropoxycarbonylamino-3-methylbutyrylamino)propionate, 4-fluorophenyl N-(1 - (1-(4-cyanophenyl)ethanesulfonyl)but-2-yl)carbamate;
other fungicides - guanidines: dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate);
- antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxins, streptomycin, validamycin A;
- nitrophenyl derivatives: binapacryl, dicloran, dinobuton, dinocap, nitrothal-isopropyl, tecnazen;
- organometallic compounds: fentin salts such as fentin acetate, fentin chloride, fentin hydroxide;
- sulfur-containing heterocyclyl compounds: isoprothiolane, dithianon;
- organophosphorus compounds: edifenphos, fosetyl, fosetyl-aluminum, iprobenfos, pyrazophos, tolclofos-methyl;
- organochlorine compounds: chlorothalonil, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4- methyl-benzene sulfonamide; - nitrophenyl derivatives: binapacryl, dinocap, dinobuton;
- inorganic active compounds: phosphorous acid and its salts, Bordeaux mixture, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate;
- others: biphenyl, bronopol, cyflufenamid, cymoxanil, diphenylamine, metrafenone, mildiomycin, oxin-copper, prohexadione-calcium, spiroxamine,
N-(cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluorophenyl)-methyl)-2- phenylacetamide, N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N- ethyl-N-methylformamidine, N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl- phenyl)-N-ethyl-N-methylformamidine, N'-(2-methyl-5-trifluoromethyl-4-(3- trimethylsilanylpropoxy)-phenyl)-N-ethyl-N-methylformamidine, N'-(5-difluoromethyl-
2-methyl-4-(3-trimethylsilanylpropoxy)-phenyl)-N-ethyl-N-methylformamidine.
Accordingly, the present invention furthermore relates to the compositions listed in Table C, where a row of Table C corresponds in each case to a fungicidal composition comprising a compound of the formula I (component 1), which is preferably one of the compounds described herein as being preferred, and the respective further active compound (component 2) stated in the row in question. According to one embodiment of the invention, component 1 in each row of Table C is in each case one of the compounds of the formula I specificially individualized in Tables 1 to 44352.
Table C
Figure imgf000188_0001
Figure imgf000189_0001
Figure imgf000190_0001
Figure imgf000191_0001
Figure imgf000192_0001
Figure imgf000193_0001
The active compounds II, mentioned above as component 2, their preparation and their action against harmful fungi are generally known (cf.: http://www.hclrss.demon.co.uk/index.html); they are commercially available. The compounds named according to IUPAC, their preparation and their fungicidal action are likewise known and described, for example, in EP-A 226 917; EP-A 10 28 125; EP-A 10 35 122; EP-A 12 01 648; WO 98/46608; WO 99/24413; WO 03/14103; WO 03/053145; WO 03/066609 and WO 04/049804, the entire contents of which is included herein by way of reference.
The present invention furthermore relates to a pharmaceutical composition comprising at least one pyrazine compound according to the invention and/or a pharmaceutically acceptable salt thereof and, if appropriate, at least one pharmaceutically acceptable carrier. The invention also relates to the pharmaceutical use of the pyrazines of the formula I according to the invention, in particular the pyrazines of the formula I described in the above description as being preferred, and/or their pharmaceutically acceptable salts, in particular their use for preparing a medicament for the treatment of cancer.
The pyrazines of the formula I according to the invention, in particular the pyrazines of the formula I according to the invention described in the above description as being preferred, and/or their pharmaceutically acceptable salts effectively inhibit the growth and/or the propagation of tumor cells, as can be demonstrated in standard tests with tumor cell lines, such as HeLa, MCF-7 and COLO 205. In particular, the pyrazines of the formula I according to the invention generally have IC50 values of < 10"6 mol/l (i.e. < 1 μM), preferably IC50 values of < 10"7 mol/l (i.e. < 100 nM), for cell cycle inhibition in HeLa cells.
The pyrazines of the formula I according to the invention, in particular the pyrazines of the formula I according to the invention described in the above description as being preferred, and/or their pharmaceutically acceptable salts are suitable for the treatment, inhibiton or control of growth and/or propagation of tumor cells and the disorders associated therewith. Accordingly, they are suitable for cancer therapy in warmblooded vertebrates, for example mammals and birds, in particular man, but also other mammals, in particular useful and domestic animals, such as dogs, cats, pigs, ruminants (cattle, sheep, goats, bison, etc.), horses and birds, such as chicken, turkey, ducks, geese, guineafowl and the like.
The pyrazines of the formula I according to the invention, in particular the pyrazines of the formula I according to the invention described in the above description as being preferred, and/or their pharmaceutically acceptable salts are suitable for the therapy of cancer or cancerous disorders of the following organs: breast, lung, intestine, prostate, skin (melanoma), kidney, bladder, mouth, larynx, oesophagus, stomach, ovaries, pancreas, liver and brain.
In addition to the pyrazine compound I according to the invention and/or its pharmaceutically acceptable salt, the pharmaceutical compositions according to the invention comprise at least optionally a suitable carrier. Suitable carriers are, for example, solvents, carriers, excipients, binders and the like customarily used for pharmaceutical formulations, which are described below in an exemplary manner for individual types of administration.
The compounds I according to the invention can be administered in a customary manner, for example orally, intravenously, intramuscularly or subcutaneously. For oral administration, the active compound can be mixed, for example, with an inert diluent or with an edible carrier; it can be embedded into a hard or soft gelatin capsule, it can be compressed to tablets or it can be mixed directly with the food/feed. The active compound can be mixed with excipients and administered in the form of indigestible tablets, buccal tablets, pastilles, pills, capsules, suspensions, potions, syrups and the like. Such preparations should contain at least 0.1 % of active compound. The composition of the preparation may, of course, vary. It usually comprises from 2 to 60% by weight of active compound, based on the total weight of the preparation in question (dosage unit). Preferred preparations of the compound I according to the invention comprise from 10 to 1000 mg of active compound per oral dosage unit. The tablets, pastilles, pills, capsules and the like may furthermore comprise the following components: binders, such as traganth, gum arabic, corn starch or gelatin, excipients, such as dicalcium phosphate, disintegrants, such as corn starch, potato starch, alginic acid and the like, glidants, such as magnesium stearate, sweeteners, such as sucrose, lactose or saccharin, and/or flavors, such as peppermint, vanilla and the like. Capsules may furthermore comprise a liquid carrier. Other substances which modify the properties of the dosage unit may also be used. For example, tablets, pills and capsules may be coated with schellack, sugar or mixtures thereof. In addition to the active compound, syrups or potions may also comprise sugar (or other sweeteners), methyl- or propylparaben as preservative, a colorant and/or a flavor. The components of the active compound preparations must, of course, be pharmaceutically pure and nontoxic at the quantities employed. Furthermore, the active compounds can be formulated as preparations with a controlled release of active compound, for example as delayed-release preparations.
The active compounds can also be administered parenterally or intraperitoneal^. Solutions or suspensions of the active compounds or their salts can be prepared with water using suitable wetting agents, such as hydroxypropylcellulose. Dispersions can also be prepared using glycerol, liquid polyethylene glycols and mixtures thereof in oils. Frequently, these preparations furthermore comprise a preservative to prevent the growth of microorganisms.
Preparations intended for injections comprise sterile aqueous solutions and dispersions and also sterile powders for preparing sterile solutions and dispersions. The preparation has to be sufficiently liquid for injection. It has to be stable under the preparation and storage conditions and it has to be protected against contamination by microorganisms. The carrier may be a solvent or a dispersion medium, for example, water, ethanol, a polyol (for example glycerol, propylene glycol or liquid polyethylene glycol), a mixture thereof and/or a vegetable oil.
The invention is further illustrated by the following, non-limiting examples.
Examples
1.) Syntheses
Example 1 :
5-Chloro-6-[2,6-difluoro-4-(3-dimethylamino-propoxy)-phenyl]-1-isobutyl-3-pyrazol-1-yl- 1 H-pyrazin-2-one 0.69 mmol of NaH were dissolved in 1 ml NMP. 3-Dimethylamino-propanol (0.63 mmol) was added slowly and the suspension was stirred for 30 min. 0.57 mmol of 5-Chloro-1- isobutyl-3-pyrazol-1-yl-6-(2,4,6-trifluoro-phenyl)-1 H-pyrazin-2-one (known from WO 2006/089060) dissolved in 1 ml NMP were added to the suspension and the reaction mixture was heated in the microwave for 4 min at 1500C. The reaction was worked up (extraction between ethyl acetate and water, drying, evaporation) and the crude product was separated through column chromatography (reversed phase, MeCN/hbO, 1 % TFA). The product was basified with Na2CC"3 solution and extracted into DCM. After evaporation the product was isolated in a yield of 15 % of the theory.
HPLC (RT): 2,822 min MS (m/z): 465,90
Example 2: 5-Chloro-6-[2,6-difluoro-4-(3-hydroxy-propoxy)-phenyl]-1 -isobutyl-3-pyrazol-1 -yl-1 H- pyrazin-2-one
0.69 mmol of NaH were dissolved in 1 ml NMP. 3-(Tetrahydro-pyran-2-yloxy)-propan-1- ol (0.63mmol) was added slowly and the suspension was stirred for 30 min. 0.57 mmol of 5-Chloro-1 -isobutyl-3-pyrazol-1 -yl-6-(2,4,6-trifluoro-phenyl)-1 H-pyrazin-2-one (known from WO 2006/089060) dissolved in 1 ml NMP were added to the suspension and the reaction mixture was heated in the microwave for 4 min at 1500C. The reaction was worked up (extraction between MTBE and water, drying, evaporation) and the crude product was separated through column chromatography (normal phase, n- heptane/ethyl acetate). Deprotection of the hydroxyl group was done in MeOH with 20 drops of 20% HCI for 15 min. The product was neutralised and extracted into ethyl acetate. After evaporation the product was isolated in a yield of 32 % of the theory.
HPLC (RT): 3,209 min MS (m/z): 439,35
Example 3:
5-Chloro-6-[2,6-difluoro-4-(3-methoxy-propoxy)-phenyl]-1 -isobutyl-3-pyrazol-1 -yl-1 H- pyrazin-2-one
0.69 mmol of NaH were dissolved in 1 ml NMP. 3-Methoxy-propan-1-ol (0.63 mmol) was added slowly and the suspension was stirred for 30 min. 0.57 mmol of 5-Chloro-1- isobutyl-3-pyrazol-1 -yl-6-(2, 4, 6-trifluoro-phenyl)-1 H-pyrazin-2-one (known from WO 2006/089060) dissolved in 1 ml NMP were added to the suspension and the reaction mixture was heated in the microwave for 4 min at 1500C. The reaction was worked up (extraction between ethyl acetate and water, drying, evaporation) and the crude product was separated through column chromatography (normal phase, n- heptane/ethyl acetate, 1 % TFA). The product was isolated in a yield of 42 % of the theory.
HPLC (RT): 3,639 min MS (m/z): 453,35
The compounds listed below were prepared in an analogous manner-
Example 4: 5-Chloro-6-[3-(3-dimethylamino-propoxy)-2-fluoro-phenyl]-1 -(2-methylbutyl)-3-pyrazol- 1 -yl-1 H-pyrazin-2-one
HPLC (RT): 2,699 min MS (m/z): 462,15
Example 5:
5-Chloro-6-[2-fluoro-3-(3-hydroxy-propoxy)-phenyl]-1 -(2-methylbutyl)-3-pyrazol-1 -yl-1 H- pyrazin-2-one
NMR (400 MHz, CDCI3): δ = 9,1 (m, 1 H); 7,9 (s, 1H); 7,1 (m, 2H); 6,9 (m, 1H); 6,5 (m, 1H); 4,3 (m, 2H), 4,0 (m, 1H); 3,9 (m, 2H); 3,7 (m,1H); 2,1 (m, 2H); 0,6-0,9 (m, 9H)
Example 6:
5-Chloro-6-[2-fluoro-3-(3-methoxy-propoxy)-phenyl]-1-(2-methylbutyl)-3-pyrazol-1-yl- 1 H-pyrazin-2-one
HPLC (RT): 3,712 min MS (m/z): 449,15
Example 7:
5-Chloro-6-[5-(3-dimethylamino-propoxy)-2-fluoro-phenyl]-1-(2-methylbutyl)-3-pyrazol- 1 -yl-1 H-pyrazin-2-one
HPLC (RT): 2,835 min MS (m/z): 462,20
Example 8:
5-Chloro-6-[2-fluoro-5-(3-hydroxy-propoxy)-phenyl]-1 -(2-methylbutyl)-3-pyrazol-1 -yl-1 H- pyrazin-2-one
NMR (400 MHz, DMSO-de): δ = 8,4 (s, 1H); 7,9 (s, 1H); 7,1 (m, 3H); 6,9 (m, 1 H); 4,9 (d, 1H), 4,3 (m, 1H); 4,0 (m, 2H); 3,4 (m,1H); 1 ,0-2,0 (m, 6H); 0,9 (m, 2H); 0,8 (m, 3H); 0,7 (m, 1H) Example 9:
5-Chloro-6-[2-fluoro-5-(3-methoxy-propoxy)-phenyl]-1-(2-methylbutyl)-3-pyrazol-1-yl- 1 H-pyrazin-2-one
HPLC (RT): 3,733 min MS (m/z): 449,10
Example 10: 5-Chloro-6-[2,6-difluoro-3-(3-dimethylamino-propoxy)-phenyl]-1 -(2-methylbutyl)-3- pyτazol-1-yl-1 H-pyrazin-2-one
HPLC (RT): 2,836 min MS (m/z): 480,1
Example 11 :
5-Chloro-6-[2,6-difluoro-3-(3-methoxy-propoxy)-phenyl]-1-(2-methylbutyl)-3-pyrazol-1- yl-1 H-pyrazin-2-one
HPLC (RT): 3,685 min MS (m/z): 467,10
2.) Fungicidal activity
Microtiter test:
The active compounds were formulated in DMSO in a stock solution having a concentration of 10 000 ppm.
Use Example 1 - Activity against grey mould caused by Botrytis cinerea in the microtiter test:
The stock solution was pipetted into a microtiter plate (MTP) and diluted with a malt- based aqueous nutrient medium for fungi to the stated active compound concentration. An aqueous spore suspension of Botrytis cinerea was then added. The plates were placed in a water vapor-saturated chamber at temperatures of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. The measured parameters were compared to the growth of the active compound-free control variant (= 100 %) and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds. In this test, the samples which had been treated with 125 ppm of the compounds from examples 1 and 4 showed a relative growth of the pathogen of at most 3%. The samples which had been treated with 31 ppm of the compounds from examples and 5 and 6 showed a relative growth of the pathogen of at most 6%.
Use Example 2 - Activity against the rice blast pathogen Pyricularia oryzae in the microtiter test:
The stock solution was pipetted into a microtiter plate (MTP) and diluted with a malt- based aqueous nutrient medium for fungi to the stated active compound concentration. An aqueous spore suspension of Pyricularia oryzae was then added. The plates were placed in a water vapor-saturated chamber at temperatures of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm on day 7 after the inoculation. The measured parameters were compared to the growth of the active compound-free control variant (= 100 %) and the fungus- and active compound-free blank value to determine the relative growth in % of the pathogens in the individual active compounds.
In this test, the samples which had been treated with 125 ppm of the compounds from examples 1 , 2, 3 and 4 showed a relative growth of the pathogen of at most 4%. The samples which had been treated with 31 ppm of the compounds from examples 5, 6, 7, 8 and 9 showed a relative growth of the pathogen of at most 2%.

Claims

We claim:
1. Pyrazine compounds of formula I, N-oxides or agriculturally useful salts thereof
Figure imgf000200_0001
where
A is O, S or NR10;
R1 is Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, C3-Cio-cycloalkyl-Ci-C4-alkyl, C3-Cio-cycloalkenyl-Ci-C4-alkyl, a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated non-aromatic carbocyclic ring optionally containing as ring members one or two groups selected from C(=O) and C(=S), phenyl, naphthyl, a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated non-aromatic heterocyclic ring attached via a carbon atom and containing 1 , 2, 3 or 4 heteroatoms selected from O, S and N as ring members and optionally containing as ring members one or two groups selected from C(=O) and C(=S), or a 5- or 6-membered heteroaromatic ring attached via a carbon atom and containing 1 , 2, 3 or 4 heteroatoms selected from O, S and N as ring members; where R1 may be partially or fully halogenated and/or may carry 1 , 2, 3 or 4 identical or different substituents L3;
or R1 is a radical of the formula NR5R6, N=CR7R8 or OR9;
R2 is a carboaromatic or heteroaromatic group selected from phenyl, benzyl, naphthyl, a 5- or 6-membered heteroaromatic radical, where the heteroaromatic radical contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members, and phenyl fused to a saturated or unsaturated aromatic or non-aromatic 5- or 6-membered heterocyclic ring, where the heterocyclic ring contains 1 , 2 or 3 heteroatoms selected from the group consisting of O, S and N as ring members and may furthermore contain 1 or 2 CO groups as ring members, where the carboaromatic or heteroaromatic group carries one substituent L1 and 1 , 2,
3 or 4 identical or different substituents L2; R3 is hydrogen, halogen, hydroxyl, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-C10- alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-C10- cycloalkyl, C3-Cio-halocycloalkyl, Ci-Cio-alkoxy, Ci-Cio-haloalkoxy , C1-C10- alkylthio, Ci-Cio-haloalkylthio, Ci-Cio-alkylsulfinyl, Ci-Cio-haloalkylsulfinyl, Ci-do-alkylsulfonyl, Ci-do-haloalkylsulfonyl, Ci-C4-alkoxy-Ci-C4-alkyl, formyl (CHO), Ci-C4-alkylcarbonyl, carboxyl (COOH), Ci-C4-alkoxy- carbonyl, SCN, cyano-Ci-C4-alkyl or cyano;
R4 is halogen, cyano, SCN, hydroxyl, mercapto, N3, Ci-Cβ-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, Ci-Cβ-alkoxy, Cs-Cs-alkenyloxy, Cs-Cs-alkynyloxy, Ci-Cβ- alkylthio, Cs-Cs-alkenylthio, Cs-Cs-alkynylthio, Ci-Cβ-alkylsulfinyl, Ci-Cβ- alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, Ci-C6-alkylaminosulfonyl, di-Ci-C6-alkylaminosulfonyl, C3-Cio-cycloalkyl, phenyl, naphthyl, 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or aromatic heterocyclic ring having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 , 2 or 3 groups selected from C(=O) and C(=S) as ring members, where the heterocyclic ring may be fused to a phenyl ring or to a 5- or 6-membered heteroaromatic ring having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S; or a radical of the formula -ON(=CRaRb), -NRcN=CRaRb, -NRaRb, -NRcNRaRb, -NRa-CN, -N=ORa; -NRcC(=W)-NRaRb, -NRaC(=W)Rc, -NNRaRbC(=W)-X1-Rc, -ONRaRb,-OC(=W)Rc, -O(C=W)NRaRb, -C(=W)RC, -C(=W)NRaRb, -C(=W)N0Rb, -CRaRb-ORc, -CRaRb-SRc, -CRaRb-NRcRd, -CRaRb-C(=W)Rc, -C(=W)-NRa-X2-Rb, -C(=NX2Ra)-ORb or -C(=NX2Ra)-SRb,
in which
W is O, S, NRd or NNRdRe;
X1 is O or NRf;
X2 is a single bond, -CO-, -CONH-, -COO-, -0-, -NRf-, -CH2-O-CO- or -CH=CH-(C=O)-, where the left part of the divalent radicals is attached to the nitrogen atom;
Ra, Rb, Rc, Rd, Re, Rf independently of one another are hydrogen, hydroxyl, Ci-Cβ-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C-i-Cβ- alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-Cβ-alkylcarbonyl, Ci-Cβ- alkoxycarbonyl, Cs-Cβ-cycloalkyl, Cs-Cβ-cycloalkenyl, C3-C6- cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, aryl, aryl-Ci-C4-alkyl or a 5- to 10-membered saturated or unsaturated, aromatic or 14 non-aromatic heterocyclic ring having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members;
where, if Ra, Rb, Rc are attached directly to an oxygen atom, they are not hydroxyl, Ci-Cβ-alkoxy or Cs-Cβ-cycloalkoxy;
or Ra and Rb together with the nitrogen atom to which they are attached form a group RC-X11-C(R9)=N in which
Ra is independently defined like Ra or is halogen or cyano; and
X11 is independently defined like X1;
or two of the radicals Ra, Rb, Rc, Rd, Re, Rf, Rs together form a C2-C4-alkylene group which may be interrupted by an oxygen atom and/or may contain a C-C double bond,
where the aliphatic, alicyclic, aromatic and/or heterocyclic groups in R4, Ra,
Rb, Rc, Rd, Re, Rf and/or Rs may be partially or fully halogenated and/or may carry 1 , 2 or 3 substituents Rx, where
Rx is cyano, SCN, nitro, hydroxyl, mercapto, oxo, Ci-Cβ-alkyl, C-i-Ce-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl,
C2-C6-haloalkynyl, Cs-Cβ-cycloalkyl, Cs-Cβ-halocycloalkyl, C3-C6- cycloalkyl-Ci-C4-alkyl, Cs-Cβ-cycloalkenyl, d-Cβ-alkoxy, C-i-Cβ- haloalkoxy, C2-C6-alkenyloxy, Cs-Cβ-alkynyloxy, Ci-C6-alkylthio, Ci-Cβ-alkylcarbonyl, carboxyl, Ci-C6-alkoxycarbonyl, Ci-Cβ- alkylsulfinyl, Ci-Cβ-alkylsulfonyl, hydroxysulfonyl, aminosulfonyl,
Ci-Cβ-alkylaminosulfonyl, di-(Ci-C6-alky)aminosulfonyl, amino, Ci-Cβ-alkylamino, di-(Ci-C6-alkyl)amino, aminocarbonyl, C-i-Cβ- alkylaminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, aminothiocarbonyl, Ci-Cβ-alkylaminothiocarbonyl, di-(Ci-C6- alkyl)aminothiocarbonyl, Ci-Cβ-alkylcarbonylamino, tri-(Ci-Cβ- alkyl)silyl, aryl, aryloxy, aryl-Ci-C4-alkyl, aryl-Ci-C4-alkoxy, 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclyl, 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclyloxy, 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclylcarbonyl, where the heterocyclyl radicals in the three last-mentioned groups contain 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members, -C(=NORα)-ORβ or -OC(Rα)2-C(Rβ)=NORβ,
where the cyclic radicals in Rx may be unsubstituted or may carry 1 , 2 or 3 radicals Ry, where
Ry is cyano, nitro, halogen, hydroxyl, d-Cε-alkyl, Ci-Cε- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cε-cycloalkyl, Cs-Cε-halocycloalkyl, C3-C6-cycloalkenyl, Ci-Cε-alkylsulfonyl, Ci-Cε-alkylsulfinyl,
Ci-Cε-alkoxy, Ci-Cε-haloalkoxy, C2-C6-alkenyloxy, Ci-Cε- alkylthio, d-Cβ-alkoxycarbonyl, amino, Ci-Cε-alkylamino, di-(Ci-C6-alkyl)amino, aminocarbonyl, Ci-Cε- alkylaminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, aminothiocarbonyl, Ci-Cε-alkylaminothiocarbonyl, di-(Ci-
C6-alkyl)aminothiocarbonyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclyl, 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclyloxy, where the heterocyclyl radicals in the two last-mentioned groups contain 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members, or -C(=NORα)-ORβ; where
Rα, Rβ independently of one another are hydrogen or Ci-Cε- alkyl;
R5 is H, Ci-Cio-alkyl, C2-Cio-hydroxyalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, C4-Cio-alkadienyl, C3-Cio-cycloalkyl, Ci-Cio-alkoxy, C2-Cio-alkenyloxy,
C2-Cio-alkynyloxy, amino, Ci-Cs-alkylamino, di-(Ci-C8-alkyl)amino, phenyl, naphthyl or a saturated or unsaturated aromatic or non-aromatic 5- or 6-membered heterocycle which is attached via a carbon atom, where the heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members and may furthermore contain 1 or 2 CO groups as ring members;
where the aliphatic, alicyclic, aromatic and/or heterocyclic groups in R5 may be partially or fully halogenated and/or may carry 1 , 2, 3 or 4 identical or different substituents Ra1;
14 R6 is independently defined like R5, or is a group #-CR61R62-(CR63R64)q- (CR65R66)p-Y-Z in which
# is the point of attachment to the nitrogen atom;
R61, R62, R63, R64, R65 and R66 independently of one another are hydrogen, C-i-Cs-alkyl, Ci-C8-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8- alkynyl, C2-C8-haloalkynyl, Cs-Cβ-cycloalkyl, Cs-Cβ-halocycloalkyl, C3-C6-cycloalkenyl, Cs-Cβ-halocycloalkenyl, phenyl, naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S; where
R63 with R61 or R66 together with the atoms to which these radicals are attached may also form a five-, six-, seven-, eight-, nine- or ten- membered saturated or partially unsaturated ring which, in addition to carbon atoms, may contain one, two or three heteroatoms from the group consisting of O, N and S as ring members and/or may carry one or more substituents Ra1;
R61 with R62, R63 with R64, R65 with R66 in each case together may also be oxygen, thus forming carbonyl groups, and form a C2-Cs-alkylene, C2-C5-alkenylene or C2-Cs-alkynylene chain (which may be interrupted by one, two or three heteroatoms from the group consisting of O, N and S), thus forming spiro groups;
R5 and R61 together with atoms to which they are attached may form a 5-, 6-, 7-, 8-, 9- or 10-membered saturated or partially unsaturated heterocycle which, in addition to carbon atoms, may contain one, two or three further heteroatoms from the group consisting of O, N and S as ring members;
where
the aliphatic, alicyclic, heterocyclic, aromatic and/or heteroaromatic radicals in R61 to R66 in each case independently of one another may be partially or fully halogenated and/or may carry one, two, three or four identical or different groups Ra1;
14 each Ra1 is independently cyano, nitro, hydroxyl, carboxyl, d-Cε-alkyl, C2-C8-alkenyl, C2-C6-alkynyl, Cs-Cβ-cycloalkyl, Cs-Cs-cycloalkenyl, d-Cβ-alkoxy, C2-C6-alkenyloxy, Cs-Cβ-alkynyloxy, Cs-Cβ-cycloalkoxy, Cs-Cβ-cycloalkenyloxy, Ci-C6-alkylthio, amino, Ci-Cβ-alkylamino, di-(Ci-C6-alkyl)amino, C(O)Rπ , C(S)Rπ , C(O)ORπ , C(S)ORπ ,
C(O)SRπ , C(S)SRπ , C(O)NH2, C(O)NHRπ , C(O)NRπ 2, OC(O)ORπ , OC(O)NH2, OC(O)NHRπ , OC(O)NRπ 2, Ci-C6-alkylene, oxy-Ci-C4-alkylene, oxy-Ci-C3-alkyleneoxy, where the three last- mentioned divalent groups may be attached to the same atom or to adjacent atoms, phenyl, naphthyl or a 5-, 6-, 7-, 8-, 9- or
10-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S;
each Rπ is independently d-Cs-alkyl, Cs-Cs-alkenyl, Cs-Cs-alkynyl, C3-C6- cycloalkyl or Cs-Cβ-cycloalkenyl;
where the aliphatic, alicyclic, aromatic or heterocyclic groups in the abovementioned groups Ra1 and Rπ for their part may be partially or fully halogenated and/or may carry one, two or three groups Rb1;
each Rb1 is independently cyano, nitro, hydroxyl, mercapto, amino, carboxyl, Ci-Cβ-alkyl, C2-C8-alkenyl, Ci-Cβ-alkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C-i-Cβ-alkylthio, Ci-Cβ-alkylamino, di-(Ci-C6- alkyl)amino, formyl, Ci-Cβ-alkylcarbonyl, Ci-Cβ-alkylsulfonyl, Ci-Cβ- alkylsulfinyl, Ci-Cβ-alkoxycarbonyl, Ci-Cβ-alkylcarbonyloxy, Ci-Cβ- alkoxycarbonyloxy, aminocarbonyl, aminothiocarbonyl, C-i-Cβ- alkylaminocarbonyl, di-(Ci-C6-alkyl)aminocarbonyl, Ci-Cβ-alkylamino- thiocarbonyl, di-(Ci-C6-alkyl)aminothiocarbonyl, C3-Cio-cycloalkyl, C3-Cio-cycloalkoxy, heterocyclyl, heterocyclyloxy, where heterocyclyl in the two lastmentioned radicals is 3- to 10-membered and contains 1 , 2, 3 or 4 heteroatoms selected from the gorup consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members; aryl, aryloxy, arylthio, aryl-Ci-Cβ-alkoxy, aryl-Ci-Cβ-alkyl, hetaryl, hetaryloxy or hetarylthio, where the aryl radicals contain 6 to 10 ring members and the hetaryl radicals 5 or 6 ring members and 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where the alicyclic, heterocyclic, aromatic and/or heteroaromatic systems may be partially or fully halogenated and/or substituted by 1 , 2, 3, 4 or 5 Ci-C4-alkyl and/or Ci-C4-haloalkyl groups;
Y is oxygen or sulfur; Z is hydrogen, carboxyl, formyl, Ci-C8-alkyl, C2-C8-alkenyl, C2-C8- alkynyl, C3-C6-cycloalkyl, C3-C8-cycloalkenyl, C(O)Rπ , C(O)ORπ , C(S)ORπ , C(O)SRπ , C(S)SRπ , C(NRA)SRπ , C(S)Rπ , C(NRπ )NRARB, C(NRπ )RA, C(NRπ )ORA C(O)NRARB, C(S)NRARB, Ci-Cβ-alkylsulfinyl, d-Cs-alkylthio, Ci-C8-alkylsulfonyl, C(O)-Ci-C4-alkylene- NRAC(NRπ )NRARB, C(S)-Ci-C4-alkylene-NRAC(NRπ )NRARB, C(NRπ )-Ci-C4-alkylene-NRAC(NRπ )NRARB, phenyl, naphthyl, a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one, two, three or four heteroatoms from the group consisting of O, N and S and which is attached directly or via a carbonyl, thiocarbonyl, CrC4- alkylcarbonyl or Ci-C4-alkylthiocarbonyl group; where the carbon chains in group Z may be substituted by one or more groups Rb1;
RA and RB independently of one another are hydrogen, C2-alkenyl, C2- alkynyl or one of the groups mentioned under Rπ ; or
RA and RB together with the nitrogen atom to which they are attached or RA and Rπ together with the carbon atoms and heteroatoms to which they are attached may also form a five- or six-membered saturated, partially unsaturated or aromatic ring which, in addition to carbon atoms, may contain one, two or three further heteroatoms from the group consisting of O, N and S as ring members and/or may carry one or more substituents Ra1;
or
Z with R64 or R66 may also form a five- or six-membered saturated or partially unsaturated ring which, in addition to carbon atoms and Y, may contain one or two further heteroatoms from the group consisting of O, N and S as ring members and/or may carry one or more substituents Ra1;
where the group Z may be partially or fully halogenated and/or carry one, two or three groups Rb1;
p is 0, 1 , 2, 3, 4 or 5; and
q is O or i ; or R5 and R6 together with the nitrogen atom to which they are attached form a saturated or unsaturated aromatic or non-aromatic 5- or 6-membered heterocycle, where the heterocycle may additionally contain 1 , 2 or 3 heteroatoms selected from the group consisting of O, S and N and/or 1 or 2 CO groups as ring members and where the heterocycle may carry 1 ,
2 or 3 substituents selected from the group consisting of halogen, hydroxyl, cyano, nitro, carboxyl, Ci-Cs-alkyl, Ci-Cs-haloalkyl, C2-C8-hydroxyalkyl, Ci-Cs-alkoxy, d-Cs-haloalkoxy, Ci-Cs-alkylthio, Ci-Cs-haloalkylthio, C2-C8- alkenyl, C2-C8-haloalkenyl, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy, C2-C8- alkynyl, Cs-Cs-haloalkynyl, C2-C8-alkynyloxy, Cs-Cs-haloalkynyloxy, C3-C8- cycloalkyl, Cs-Cs-cycloalkoxy, Cs-Cs-cycloalkenyl, Cs-Cs-cycloalkenyloxy, amino, Ci-Cs-alkylamino, di-(Ci-C8-alkyl)amino, Ci-Cs-alkylcarbonyl, Ci-Cs- haloalkylcarbonyl, C2-C8-alkenylcarbonyl, C2-C8-haloalkenylcarbonyl, C2-C8- alkynylcarbonyl, Cs-Cs-haloalkynylcarbonyl, Cs-Cs-cycloalkylcarbonyl, C3-C8-cycloalkenylcarbonyl, Ci-Cs-alkylcarbonyloxy, Ci-Cs- haloalkylcarbonyloxy, C2-C8-alkenylcarbonyloxy, C2-C8- haloalkenylcarbonyloxy, C2-C8-alkynylcarbonyloxy, C3-C8- haloalkynylcarbonyloxy, Cs-Cs-cycloalkylcarbonyloxy, C3-C8- cycloalkenylcarbonyloxy, Ci-Cs-alkoxycarbonyl, Ci-Cs-haloalkoxycarbonyl, C2-C8-alkenyloxycarbonyl, C2-C8-haloalkenyloxycarbonyl, C2-C8- alkynyloxycarbonyl, Cs-Cs-haloalkynyloxycarbonyl, C3-C8- cycloalkoxycarbonyl, cycloalkenyloxycarbonyl, aminocarbonyl, Ci-Cs- alkylaminocarbonyl, di-(Ci-C8-alkyl)aminocarbonyl, Ci-Cs-alkoxy- carbonyloxy, Ci-Cs-haloalkoxycarbonyloxy, C2-C8-alkenyloxycarbonyloxy, C2-C8-haloalkenyloxycarbonyloxy, C2-C8-alkynyloxycarbonyloxy, C3-C8- haloalkynyloxycarbonyloxy, Cs-Cs-cycloalkoxycarbonyloxy, cycloalkenyloxycarbonyloxy, aminocarbonyloxy, Ci-Cs- alkylaminocarbonyloxy and di-(Ci-C8-alkyl)aminocarbonyloxy;
R7 and R8, independently of each other, are hydrogen, d-d-alkyl, C1-C4- haloalkyl or C3-Cio-cycloalkyl;
or R7 and R8 together with the nitrogen atom to which they are attached form a saturated or unsaturated aromatic or non-aromatic 5- or 6-membered heterocyclic ring, where the heterocyclic ring may additionally contain 1 , 2 or 3 heteroatoms selected from the group consisting of O, S and N and/or 1 or 2 CO groups as ring members and where the heterocyclic ring may carry 1 , 2 or 3 substituents selected from the group consisting of halogen, hydroxyl, d-d-alkyl, d-d-haloalkyl, Ci-d-alkoxy and d-d-haloalkoxy;
14 R9 is hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, C3-Cio-cycloalkyl or C3-Cio-cycloalkenyl, where the five last-mentioned radicals may be partially or fully halogenated and/or may carry 1 , 2, 3 or 4 identical or different substituents selected from cyano, SCN, Ci-C4-alkyl, C3-C10- cycloalkyl, C3-Cio-cycloalkenyl, Ci-Cβ-alkoxy, d-Cε-thioalkyl, Ci-Cβ- alkylcarbonyl, Ci-Cβ-alkoxycarbonyl, Ci-Cε-alkylamino, di-(Ci-C6-alkyl)- amino, tri-(Ci-C4-alkyl)-silyl and a group #-CR61R62-(CR63R64)q-(CR65R66)P-Y- Z, where #, R61, R62, R63, R64, R65, R66, Y, Z, q and p are as defined above;
R10 is hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, Ci-Cio-alkylcarbonyl or Ci-Cio- alkoxycarbonyl;
L1 is a group of the formula -Y1-Y2-T, -C(RV)=C(RW)-Y1-Y2-T or -C≡C-Y1-Y2-T in which Y1 is CRhR', C(=T2)O, C(=T2)NRh, OC(=T2), O, NRh or S(O)r;
Y2 is d-Cs-alkylene, C2-Cs-alkenylene or C2-Cs-alkynylene, where Y2 may be interrupted by one, two, three or four heteroatoms from the group consisting of NRh, O and S(O)r; r is O, 1 or 2; T is V1Rh, V1RZ, NRhR', V1NRhR', C(O)ORh, C(O)NRhR', S(O)rRh,
C(NORh)R',NRh-T1-C(=T2)-T3, T1-C(=T2)-[(Y2)b-C(=T2)]c-T3, T1- C(=T2)-[Y2-T1-C(=T2)]c-T3, T1-C(=T2)-[T1-Y2-C(=T2)]c-T3 or T1- C(=T2)-[NRh-(NR')b-C(=T2)]c-T3, in which T1 is a direct bond, O, S or NRh; T2 is O, S or NRh;
T3 is Rh, Rz, ORh, SRh or NRhR'; V1 is O or S; b is O or i ; c is 0, 1 , 2, 3, 4 or 5; Rz is NR5R6 or Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl,
C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3- Ci2-cycloalkenyl, Cs-C^-halocycloalkenyl, phenyl, halophenyl, naphthyl, halonaphthyl or a 5-, 6-, 7-, 8-, 9-, or 10-membered saturated, partially unsaturated or aromatic heterocyclic ring which is attached via carbon, which may be partially or fully halogenated and contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur; where Rz may contain 1 , 2, 3 or 4 identical or different groups Ra1, where R5, R6 and Ra1 are as defined above; each Rh and each R1, independently of each other, are hydrogen, Ci- Cs-alkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, Cs-Cβ-cycloalkyl, C3-C6- 14 cycloalkenyl, phenyl, naphthyl, a 5-, 6-, 7-, 8-, 9- or 10- membered saturated, partially unsaturated or aromatic heterocyclic ring which contains 1 , 2, 3 or 4 heteroatoms from the group consisting of O, N and S, where the groups Rh and R1 may be partially or fully halogenated and where the aliphatic, alicyclic, aromatic or heterocyclic groups in the abovementioned groups Rh and R1 for their part may carry one, two or three groups Rb1, where Rb1 is as defined above; Rv and Rw, independently of each other, are hydrogen, halogen, hydroxy, CN, nitro, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkinyl, Ci-Cio-haloalkyl, C2-Cio-haloalkenyl, C2-Cio-haloalkinyl, C3-C10- cycloalkyl, C3-Cio-halocycloalkyl, C3-Cio-cycloalkenyl, C3-C10- halocycloalkenyl, ORD, S(O)rRD, NRDRE, CO-RE, COORE, CONRDRE, CRD(=N)ORE; phenyl, napthyl, an aromatic heterocyclic ring which is attached via a carbon atom and which may be partially or fully halogenated and contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur, which aromatic groups may be substituted by 1 to 5 radicals RF; where
RF is halogen, hydroxy, CN, nitro, Ci-Cio-alkyl, C2-C10- alkenyl, C2-Cio-alkinyl, Ci-Cio-haloalkyl, C2-Cio-halo- alkenyl, C2-Cio-haloalkinyl, C3-Cio-cycloalkyl, C3-Cio-halo- cycloalkyl, C3-Cio-cycloalkenyl, C3-Cio-halocycloalkenyl, Ci-Ce-alkoxy, CrC6-haloalkoxy, CrC6-alkylthio, CrC6- haloalkylthio, CrC6-alkylsulfinyl, CrC6-haloalkylsulfinyl, Ci-Ce-alkylsulfonyl, CrC6-haloalkylsulfonyl, (CrC6- alkoxy)carbonyl, (CrC6-haloalkoxy)carbonyl, NRGRH, CORGRH, CO-NRGRH or CRG(=N)ORH, wherein RG and RH are, independently of one another, Ci-Cβ-alkyl or C-i-Cβ-haloalkyl;
RD,RE, independently of each other, are hydrogen, halogen, hydroxy, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkinyl, Ci-Cio-haloalkyl, C2- Cio-haloalkenyl, C2-Cio-haloalkinyl, C3-Cio-cycloalkyl, C3-C10- halocycloalkyl, C3-Cio-cycloalkenyl, Cs-Cio-halocycloalkenyl, or unsubstituted or substituted phenyl, napthyl or an aromatic heterocyclic ring which is as defined in Rv; each L2 is independently halogen, hydroxyl, mercapto (SH), cyano, cyanato (OCN), nitro, carboxyl (COOH), Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-C10- hydroxyalkyl, Ci-Cio-alkoxy, Ci-Cio-haloalkoxy, Ci-Cio-alkylthio, C1-C10- haloalkylthio, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkenyloxy, C2-C10- alkynyl, C3-Cio-haloalkynyl, C2-Cio-alkynyloxy, C3-Cio-cycloalkyl, C3-C10- 14 halocycloalkyl, C3-Cio-cycloalkoxy, C3-Cio-cycloalkyl-Ci-C4-alkyl, C3-C10- cycloalkenyl, Ci-Cio-alkoxycarbonyl, Ci-Cio-haloalkoxycarbonyl, C2-C10- alkenyloxycarbonyl, C2-Cio-alkynyloxycarbonyl, Ci-do-alkylcarbonyloxy, C-i-do-alkenylcarbonyloxy, Ci-Cio-alkynylcarbonyloxy, aminocarbonyl, Ci-Cio-alkylaminocarbonyl, di-(Ci-Cio-alkyl)aminocarbonyl, C1-C10- alkoximinoalkyl, C2-Cio-alkenyloximinoalkyl, C2-Cio-alkynyloximinoalkyl, formyl, Ci-do-alkylcarbonyl, C2-Cio-alkenylcarbonyl, C2-C10- alkynylcarbonyl, C3-C6-cycloalkylcarbonyl, NRjRk, NRJ-(C=O)-Rk, S(=O)nA1, C(=S)A2, a group -C(=N-OR')(NRmRn), a group -C(=N-NR°Rp)(NRqRr) or tri- (Ci-C4)alkylsilyl;
in which
RJ, Rk, R1, Rm, Rn, R0, RP, R^, Rr are each independently H, Ci-C8- alkyl, d-Cs-haloalkyl, C2-C8-hydroxyalkyl, C2-C8-alkenyl, C2-C8- haloalkenyl, C2-C8-alkynyl, Cs-Cs-cycloalkyl or C3-C8- cycloalkenyl; or
Rm and Rn, R0 and RP and/or R? and Rr together with the nitrogen atom to which they are attached form a four-, five- or six- membered saturated or partially unsaturated ring which may carry one, two, three or four substituents independently of one another selected from L5;
A1 is hydrogen, hydroxyl, d-Cs-alkyl, amino, d-Cs-alkylamino or di-(Ci-C8-alkyl)amino;
A2 is C2-C8-alkenyl, d-Cs-alkoxy, d-Cβ-haloalkoxy, C2-C10- alkenyloxy, C2-Cio-alkynyloxy or one of the groups mentioned under A1; and
n is O, 1 or 2;
each L3 is independently halogen, hydroxyl, mercapto (SH), cyano, cyanato (OCN), nitro, carboxyl (COOH), Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-C10- hydroxyalkyl, Ci-Cio-alkoxy, Ci-Cio-haloalkoxy, Ci-Cio-alkylthio, C2-C10- alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkenyloxy, C2-Cio-alkynyl, C3-C10- cycloalkyl, C3-Cio-cycloalkoxy, C3-Cio-cycloalkyl-Ci-C4-alkyl, C3-C10- cycloalkenyl, Ci-Cio-alkoxycarbonyl, Ci-Cio-haloalkoxycarbonyl, C2-C10- alkenyloxycarbonyl, Ci-Cio-alkylcarbonyloxy, Ci-Cio-alkenylcarbonyloxy, aminocarbonyl, Ci-Cio-alkylaminocarbonyl, di-(Ci-Cio-alkyl)aminocarbonyl, 14 Ci-Cio-alkoximinoalkyl, C2-Cio-alkenyloximinoalkyl, formyl, C1-C10- alkylcarbonyl, C2-Cio-alkenylcarbonyl, Cs-Cβ-cycloalkylcarbonyl, NRRk, NRJ- (C=O)-Rk, S(=O)nA1, C(=S)A2, a group -C(=N-OR')(NRmRn), a group -C(=N- NR0Rp)(NR^RO or tri-(Ci-C4)alkylsilyl, where RJ, Rk, R1, Rm, Rn, R0, RD, R^, Rr, A1, A2 and n are as defined above;
or is a group #-(CR61R62)Pi-(CR63R64)q-(CR65R66)P-Y-Z, where #, R61, R62, R63, R64, R65, R66, Y, Z, q and p are as defined above and p1 is 0 or 1 ;
or is phenyl, naphthyl or a saturated or unsaturated aromatic or non- aromatic 5-, 6-, 7-, 8-, 9- or 10-membered heterocyclic ring, where the heterocyclic ring contains 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members and may furthermore contain one or two CO groups as ring members, where the aliphatic, alicyclic, aromatic and heterocyclic groups in L3 for their part may be partially or fully halogenated and/or may carry 1 , 2 or 3 substituents L4;
each L4 is independently cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Ci-Cβ-alkyl, C-i-Cβ-haloalkyl, C2-C8- alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, C4-C8- alkadienyl, C2-C8-alkenyloxy, C2-C8-alkynyloxy, Ci-Cβ-alkoxy, C-i-Cβ- haloalkoxy, d-Cβ-alkylthio, Ci-Cβ-alkylamino, di-(Ci-C6-alkyl)amino, Cs-C8- cycloalkylamino, (Ci-C6-alkyl)(C3-C8-cycloalkyl)amino, formyl, C-i-Cβ- alkylcarbonyl, Ci-Cβ-alkylsulfonyl, Ci-Cβ-alkylsulfinyl, Ci-Cβ-alkoxycarbonyl, Ci-Cβ-alkylcarbonyloxy, Ci-Cβ-alkylaminocarbonyl, di-(Ci-C6- alkyl)aminocarbonyl, Ci-Cβ-alkylaminothiocarbonyl, di-(Ci-C6- alkyl)aminothiocarbonyl, tri-(Ci-C4-alkyl)silyl, C3-C8-cycloalkyl, C3-C8- halocycloalkyl, bicycloalkyl, C3-C8-cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, arylthio, aryl-Ci-Cβ-alkoxy or aryl-Ci-Cβ-alkyl, where the heterocyclyl radicals may be saturated or unsaturated, aromatic or non-aromatic and have 5 to 10 ring members and 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N and optionally one or two carbonyl groups as ring members and where the cyclic systems may be partially or fully halogenated and/or substituted by d-Cβ-alkyl or C-i-Cβ-haloalkyl groups; and
each L5 is in each case independently selected from the group consisting of hydroxyl, cyano, nitro, Ci-C8-alkyl, Ci-C8-haloalkyl, C2-C8-hydroxyalkyl, Ci-C8-alkoxy, Ci-C8-haloalkoxy, Ci-C8-alkylthio, C2-C8-alkenyl, C2-C8- haloalkenyl, C2-C8-alkenyloxy, C2-C8-alkynyl, C2-C8-alkynyloxy, C3-C8- cycloalkyl, amino, Ci-C8-alkylamino and di-(Ci-C8-alkyl)amino. 14
2. The pyrazine compounds as claimed in claim 1 , where
L1 is a group of the formula -Y1-Y2-T in which
Y1 is CRhR', C(O)O, C(O)NRh, O, NRh or S(O)r; Y2 is Ci-Cs-alkylene, C2-C8-alkenylene or C2-C8-alkynylene, where
Y2 may be interrupted by one, two, three or four heteroatoms from the group consisting of NRh, O and S(0)r; r is O, 1 or 2;
T is ORh, NRhR', C(O)ORh, C(O)NRhR', C(NORh)R' or T1-C(=T2)-T3 in which
T1 is O or NRh; T2 is O, S or NRh; T3 is Rh, ORh, SRh or NRhR';
Rh and R1, independently of each other, are hydrogen, Ci-Cs-alkyl, Cs-Cs-alkenyl, Cs-Cs-alkynyl, Cs-Cβ-cycloalkyl or C3-C6- cycloalkenyl.
3. The pyrazine compounds as claimed in any of claims 1 or 2, where A is O or S.
4. The pyrazine compounds as claimed in claim 3, where A is O.
5. The pyrazine compounds as claimed in any of the preceding claims, where R1 is Ci-Cio-alkyl, C2-Cio-alkenyl, C3-Cio-alkynyl, C3-Cio-cycloalkyl, C3-Cio-cycloalkyl- Ci-C4-alkyl, phenyl, a 5- or 6-membered saturated or partially unsaturated non- aromatic heterocyclic ring attached via a carbon atom and containing 1 , 2, 3 or 4 heteroatoms selected from O, S and N as ring members and optionally containing as ring members one or two groups C(=O), or a 5- or 6-membered heteroaromatic ring attached via a carbon atom and containing 1 , 2, 3 or 4 heteroatoms selected from O, S and N as ring members; where R1 may be partially or fully halogenated and/or may carry 1 , 2, 3 or 4 identical or different substituents L3, where L3 is as defined in claim 1.
6. The pyrazine compounds as claimed in any of the preceding claims, where L3 is halogen, hydroxyl, Ci-Cio-alkyl, Ci-Cio-haloalkyl, Ci-Cio-alkoxy, C1-C10- haloalkoxy, Ci-Cio-alkylthio, Ci-Cio-haloalkylthio, C3-Cio-cycloalkyl, C3-C10- halocycloalkyl, C3-Cio-cycloalkenyl, Ci-Cio-alkylcarbonyl, C1-C10- haloalkylcarbonyl, Ci-do-alkoxycarbonyl, Ci-do-haloalkoxycarbonyl, Ci-Cs- alkylsulfonyl, d-Cs-haloalkylsulfonyl, phenyl which is unsubstituted or carries 1 , 2 or 3 substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, a 5- or 6-membered saturated or partially unsaturated non-aromatic heterocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from O, S and N as ring members, or a 5- or 6-membered
M/48014 heteroaromatic ring containing 1 , 2, 3 or 4 heteroatoms selected from O, S and N as ring members.
7. The pyrazine compounds as claimed in claim 5, where R1 is Ci-Cio-alkyl.
8. The pyrazine compounds as claimed in claim 7, where R1 is branched C3-C8- alkyl.
9. The pyrazine compounds as claimed in any of claims 1 to 3, where R1 is NR5R6, where
R5 is d-Cs-alkyl or Ci-C8-haloalkyl and
R6 is H, d-Cs-alkyl or Ci-C8-haloalkyl; or
R5 and R6 together with the nitrogen atom to which they are attached form a saturated or unsaturated 5- or 6-membered heterocyclic ring, where the heterocyclic ring may additionally contain a heteroatom or a heteroatom- containing group selected from the group consisting of O, N and NR' as ring member, where R' is H, d-Cs-alkyl, d-Cs-haloalkyl or C2-C8-hydroxyalkyl and where the heterocyclic ring may carry 1 , 2 or 3 substituents selected from the group consisting of halogen, hydroxyl, d-Cs-alkyl, d-Cs-haloalkyl, C2-C8-hydroxyalkyl, d-Cs-alkoxy and d-Cs-haloalkoxy.
10. The pyrazine compounds as claimed in any of claims 1 3, where
R5 is H, d-Cs-alkyl or d-Cs-haloalkyl and
R6 is a group #-CR61R62-(CR63R64)q-(CR65R66)P-Y-Z in which R61, R62, R63, R64, R65, R66, Y, Z, p and q are as defined in claim 1.
1 1. The pyrazine compounds as claimed in any of the preceding claims, where R2 is phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadizolyl or tetrazolyl which carries one substituent L1 and 1 or 2 substituents L2, where L1 and L2 are as defined in claim 1.
12. The pyrazine compounds as claimed in claim 1 1 , where R2 is phenyl which carries one substituent L1 in the 3-, 4- or 5-position, one substituent L2 in the 2- position and optionally one further substituent L2 in the 6-position
M/48014
13. The pyrazine compounds as claimed in any of the preceding claims, where L1 is a radical L11 of the formula
Figure imgf000214_0001
in which
Aα is Ci-C4-alkylene; γα 1 γ α 2 jn(jepenc|ent|y of One another are O, S or NRhCt;
T is ORhα, SRhα or NRhαR'α; Rhα and R'α independently of one another are H or Ci-C4-alkyl; and a is 1 , 2, 3 or 4.
14. The pyrazine compounds as claimed in any of claims 1 to 12, where L1 is a radical L12 of the formula Yβ-Aβ-Tβ in which
Yβ is CH2, O, S or NRhβR|β;
Aβ is d-Cs-alkylene;
Tβ is ORhβ, NRhβR|β or OC(=O)-T3β; T3β is Rhβ, ORhβ or NRhβR|β; and
Rhβ and R|β independently of one another are H or Ci-C4-alkyl.
15. The pyrazine compounds as claimed in claim 14, where Yβ is O; Aβ is C-i-Cε-alkylene; and
Tβ is ORhβ or NRhβR|β, where Rhβ and R|β are as defined in claim 14.
16. The pyrazine compounds as claimed in any of claims 1 to 12, where L1 is a radical L13 of the formula
Figure imgf000214_0002
in which
Y17 is -CONRh7 Or -COO; Aγ is C2-C6-alkylene; Tγ is ORhγ, NRhγR'γ or OC(=O)-T3γ; T3γ is Rhγ, ORhγ or NRhγR'γ; and
Rhγ and R'γ independently of one another are H or Ci-C4-alkyl.
17. The pyrazine compounds as claimed in any of the preceding claims, where L2 is halogen.
M/48014
18. The pyrazine compounds as claimed in any of the preceding claims, where R3 is halogen, d-Cs-alkyl, d-Cs-haloalkyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy or CN.
19. The pyrazine compounds as claimed in claim 18, where R3 is halogen.
20. The pyrazine compounds as claimed in any of the preceding claims, where R4 is a radical R4a which is a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or aromatic heterocyclic ring having 1 , 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and optionally 1 or 2 carbonyl groups as ring members, where the heterocyclic ring may be fused to a phenyl ring or to a 5- or 6-membered heteroaromatic ring having 1 , 2 or 3 heteroatoms selected from the group consisting of O, N and S, and where R4a may be partially or fully halogenated and/or carry 1 , 2 or 3 radicals Rx, where Rx is as defined in claim 1.
21. The pyrazine compounds as claimed in claim 20, where R4a is unsubstituted or carries 1 or 2 substituents selected from the group consisting of CN, halogen, d-d-alkyl, d-d-haloalkyl, d-d-alkoxy and d-d-haloalkoxy.
22. The pyrazine compounds as claimed in any of claims 20 or 21 , where R4a is a radical R4aa which is a 5- or 6-membered heteroaromatic ring which contains a nitrogen atom and optionally 1 or 2 further heteroatoms selected from the group consisting of O, N and S as ring members.
23. The pyrazine compounds as claimed in any of claims 20 or 21 , where R4a is a radical R4ab which is a 5- or 6-membered saturated or partially unsaturated non- aromatic heterocyclic ring which contains one nitrogen atom and optionally 1 or 2 further heteroatoms selected from the group consisting of O, N and S and/or one or two carbonyl groups as ring members.
24. The pyrazine compounds as claimed in any of claims 1 to 19, where R4 is CN, SCN or a radical R4b of the formula -ON(=CRaRb), -NRcN=CRaRb, -N=ORa; -NRcC(=W)-NRaRb, -NRaC(=W)Rc, -NNRaRbC(=W)-X1-Rc, -OC(=W)RC, -O(C=W)NRaRb, -C(=W)RC, -C(=W)NRaRb, -C(=W)NORb, -CRaRb-C(=W)Rc, -C(=W)-NRa-X2-Rb, -C(=NX2Ra)-ORb or -C(=NX2Ra)-SRb, where Ra, Rb, Rc, W, X1 and X2 are as defined in claim 1.
25. The pyrazine compounds as claimed in any of claims 1 to 19, where R4 is a radical R4c of the formula -NRaRb, -NRcNRaRb, -NRa-CN, -CRaRb-ORc, -CRaRb-SRc or -CRaRb-NRcRd, where Ra, Rb, Rc and Rd are as defined in claim 1.
M/48014
26. The pyrazine compounds as claimed in any of claims 24 or 25, where W is O and Ra, Rb, Rc and Rd are, independently of each other, selected from hydrogen, hydroxyl, d-Ce-alkyl, d-Ce-hydroxyalkyl, C2-C8-alkenyl, C2-C8-alkynyl, Ci-C6- alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-Cβ-alkylcarbonyl, Ci-Cβ-alkoxycarbonyl, C3-C6-cycloalkyl, Cs-Cβ-cycloalkenyl, Cs-Cβ-cycloalkoxy and Cs-Cβ-cycloalkyl-
Ci-C4-alkyl, where the 12 last-mentioned radicals may be partially or fully halogenated and/or where the cycloalkyl and/or cycloalkenyl radicals may carry 1 or 2 Ci-C4-alkyl groups; or
Ra and Rb and/or Rc and Rd together form a linear C2-C4-alkylene group which may be interrupted by an oxygen atom and/or may contain a C-C double bond and/or may carry 1 or 2 Ci-C4-alkyl groups.
27. A fungicidal composition comprising at least one pyrazine compound as defined in any of claims 1 to 26 and/or at least one N-oxide and/or at least one agriculturally acceptable salt thereof and at least one liquid or solid carrier.
28. The use of pyrazine compounds as defined in any of claims 1 to 26 or of N-oxides or of agriculturally acceptable salts thereof for controlling harmful fungi.
29. A method for controlling harmful fungi, which comprises treating the fungi, their habitat or the materials, plants, seed or soils to be protected against fungal attack with at least one pyrazine compound which is as defined in any of claims 1 to 26 or with an N-oxide or with an agriculturally acceptable salt thereof or with the composition as defined in claim 27.
30. A pharmaceutical composition comprising at least one pyrazine compound as defined in any of claims 1 to 26 and/or at least one N-oxide and/or at least one pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable carrier.
31. The use of pyrazine compounds as defined in any of claims 1 to 26 or of N-oxides or of pharmaceutically acceptable salts thereof for preparing a medicament for the treatment of cancer.
32. A method for treating cancer, which comprises treating an individual in need thereof with at least one pyrazine compound which is as defined in any of claims 1 to 26 or with an N-oxide or with an agriculturally acceptable salt thereof or with the composition as defined in claim 30.
M/48014
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