WO2010146116A1 - Composés de triazole portant un substituant soufré - Google Patents

Composés de triazole portant un substituant soufré Download PDF

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WO2010146116A1
WO2010146116A1 PCT/EP2010/058541 EP2010058541W WO2010146116A1 WO 2010146116 A1 WO2010146116 A1 WO 2010146116A1 EP 2010058541 W EP2010058541 W EP 2010058541W WO 2010146116 A1 WO2010146116 A1 WO 2010146116A1
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het
compounds
formula
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combination
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Sarah Ulmschneider
Jochen Dietz
Jens Renner
Thomas Grote
Wassilios Grammenos
Bernd Müller
Jan Klaas Lohmann
Marianna Vrettou-Schultes
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention relates to novel triazole compounds of the formulae I and Il as defined below which carry a sulfur substituent, to agricultural compositions containing them, to their use as fungicides and to intermediate compounds used in the method of producing them.
  • 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 96/41804, WO 96/16048, WO 97/41107, WO 97/43269 and WO 97/44331 describe sulfurized triazolyl derivatives. The compounds are used for combating harmful fungi.
  • triazole compounds of the general formulae I and II defined below, and by the agriculturally acceptable salts of the compounds I and II.
  • the present invention relates to triazole compounds of the formulae I and Il and to agriculturally useful salts thereof
  • Ar is phenyl which may carry 1 , 2, 3, 4 or 5 substituents R 2 , or is a 3-, 4-, 5-, 6- or 7- membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2, 3 or 4 substituents R 3 ;
  • Het is a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2, 3 or 4 substituents R 4 ;
  • A is a linear d-Cs-alkylene bridge which may be substituted by 1 , 2, 3 or 4 substituents R 5 ;
  • Y is O, S or NR 6 ;
  • Ar, Het, A and Y are as defined for formulae I and II;
  • # is the attachment point to the remainder of the molecule
  • each R 2 is independently selected from halogen, OH, SH, NO 2 , CN, Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3- Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkenyloxy, Ci-C4-haloalkenyloxy, Ci-C4-alkynyloxy, Ci-C4-haloalkynyloxy, C3-C8- cycloalkoxy, Cs-Cs-halocycloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkenylylthio, Ci
  • each R 3 is independently selected from halogen, OH, SH, NO2, CN, Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3- Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkenyloxy, Ci-C4-haloalkenyloxy, Ci-C4-alkynyloxy, Ci-C4-haloalkynyloxy, C3-C8- cycloalkoxy, Cs-Cs-halocycloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkenylylthio, Ci-C
  • each R 4 is independently selected from halogen, OH, SH, NO2, CN, Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3- Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkenyloxy, Ci-C4-haloalkenyloxy, Ci-C4-alkynyloxy, Ci-C4-haloalkynyloxy, C3-C8- cycloalkoxy, Cs-Cs-halocycloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkenylylthio, Ci-C
  • each R 5 is independently selected from halogen, OH, SH, NR 13 R 14 , Ci-C 4 -alkyl, Ci-C 4 - haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci- C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio, where the aliphatic moieties in the above radicals may carry 1 , 2 or 3 substituents R 15 ; or
  • R 6 is selected from hydrogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C 2 -C 4 - haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, phenyl, phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R 11 ; COR 12 , COOR 12 , CONR 13 R 14 and
  • each R 7 is independently selected from halogen, OH, SH, NR 13 R 14 , CN, NO 2 , Ci-C 4 - alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C 2 -C 4 - haloalkynyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and Ci-C 4 - haloalkylthio, where the aliphatic moieties in the above radicals may carry 1 , 2 or
  • R 8 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, Ci-Cio-alkoxy, C1-C10- haloalkoxy, Ci-Cio-aminoalkyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R 7 , a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2 or 3 substituents R 7 , and NR 13 R 14 ;
  • R 9 and R 10 are selected from Ci-Cio-alkyl, Ci-Cio- haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, Ci-Cio-alkoxy, Ci-Cio-haloalkoxy, Ci-C 4 - alkoxy-Ci-Cio-alkyl, Ci-C4-alkoxy-Ci-Cio-alkoxy, Ci-Cio-alkylthio, C1-C10- haloalkylthio, C2-Cio-alkenyloxy, C2-Cio-alkenylthio, C2-Cio-alkynyloxy, C2-C10- alkynylthi
  • each R 11 is independently selected from halogen, OH, SH, NR 13 R 14 , CN, NO 2 , CrC 4 - alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 - haloalkynyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio and CrC 4 - haloalkylthio, where the aliphatic moieties in the above radicals may carry 1 , 2 or 3 substituents R 15 ; each R 12 is independently selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, Ci-C4-aminoalkyl, phenyl
  • each R 13 is independently selected from hydrogen and Ci-Cs-alkyl
  • each R 14 is independently selected from hydrogen, Ci-Cs-alkyl, phenyl, and phenyl-Ci- C 4 -alkyl;
  • R 13 and R 14 together form a linear C4- or Cs-alkylene bridge or a group -CH2CH2OCH2CH2- or -CH 2 CH 2 NR 17 CH 2 CH 2 -;
  • each R 15 is independently selected from nitro, CN, OH, SH, COR 12 , COOR 12 ,
  • each R 16 is independently selected from nitro, CN, OH, SH, COR 12 , COOR 12 ,
  • each R 17 is independently selected from hydrogen and Ci-C4-alkyl
  • Q is O or S
  • M is a metal cation equivalent or an ammonium cation of formula (NR a R b R c R d ) + , wherein R a , R b , R c and R d , independently of each other, are selected from hydrogen, Ci-Cio-alkyl, phenyl and benzyl, where the phenyl moiety in the 2 last- mentioned radicals may carry 1 , 2 or 3 substituents independently selected from halogen, CN, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and NR 13 R 14 ;
  • n O, 1 or 2;
  • p 1 or 2.
  • the present invention also provides the use of triazole compounds of the formulae I and Il and/or their agriculturally useful salts for controlling harmful fungi.
  • the invention further provides fungicidal compositions comprising these triazole com- pounds of the formulae I and/or Il (and/or also of the formula IV; see below) and/or their agriculturally acceptable salts and suitable carriers. Suitable agriculturally acceptable carriers are described below.
  • the compounds I and Il can exist as one or more stereoisomers.
  • the various stereoi- somers 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 and II.
  • 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, tetrabutylammo- nium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium and sulfoxonium
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen- sulfate, 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 or Il with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • C n -Cm indicates the number of carbon atoms possible in each case in the substituent or sub- stitutent moiety in question:
  • Halogen fluorine, chlorine, bromine and iodine
  • C 2 -C 3 - Alkyl is ethyl, n-propyl or isopropyl.
  • Ci-C 2 -Alkyl is methyl or ethyl.
  • CrC 4 -AIkVl is methyl, ethyl, 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, 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.
  • Ci-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, 2-propylheptyl, 3-propylheptyl and positional isomers thereof.
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2 (Ci-C 2 -haloalkyl), 1 to 3 (Ci-C 3 -haloalkyl), 1 to 4 (Ci-C 4 -haloalkyl), 1 to 6 (Ci-C 6 -haloalkyl), 1 to 8 (CrC 8 - haloalkyl), 1 to 10 (Ci-Cio-haloalkyl) or 2 to 10 (C 2 -Cio-haloalkyl) 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-C 2 -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoro- methyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl
  • Ci-C 3 -Haloalkyl is additionally, for example, 1 ,1 ,1-trifluoroprop-2-yl, 3,3,3-trifluoropropyl or heptafluoropropyl.
  • CrC 4 - Haloalkyl is additionally, for example, 1-chlorobuty, 2-chlorobutyl, 3-chlorobutyl or 4- chlorobutyl.
  • Ci-Cio-Hydroxyalkyl straight-chain or branched alkyl groups having 1 to 2 (Ci-C 2 - hydroxyalkyl), 1 to 4 (Ci-C 4 -hydroxyalkyl), 2 to 4 (C 2 -C 4 -hydroxyalkyl), 1 to 6 (Ci-C 6 - hydroxyalkyl), 2 to 6 (C 2 -C 6 -hydroxyalkyl), 1 to 8 (Ci-C 8 -hydroxyalkyl), 2 to 8 (C 2 -C 8 - hydroxyalkyl), 1 to 10 (Ci-Cio-hydroxyalkyl) or 2 to 10 (C 2 -Cio-hydroxyalkyl) 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.
  • Haloalkenyl and the haloalkenyl moieties in haloalkenyloxy, haloalkenylcarbonyl and the like unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (C 2 - C 4 -haloalkenyl), 2 to 6 (C 2 -C 6 -haloalkenyl), 2 to 8 (C 2 -C 8 -haloalkenyl) or 2 to 10 (C 2 - Cio-haloalkenyl) 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;
  • C 3 -C6-cycloalkyl-Ci-C2-alkyl a Ci-C2-alkyl residue, as decribed above, wherein one of the hydrogen atoms is replaced by a C 3 -C6-cycloalkyl group.
  • Examples are cyclopro- pylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyl-1 -ethyl, cyclobutyl-1 -ethyl, cyclopentyl-1 -ethyl, cyclohexyl-1 -ethyl, cyclopropyl-2-ethyl, cyclobu- tyl-2-ethyl, cyclopentyl-2-ethyl, cyclohexyl-2-ethyl and the like.
  • C 3 -Cio-cycloalkyl-Ci-C4- alkyl is a Ci-C4-alkyl residue, as decribed above, wherein one of the hydrogen atoms is replaced by a C 3 -Cio-cycloalkyl group.
  • Examples are, apart those mentioned above for C 3 -C6-cycloalkyl-Ci-C4-alkyl, cycloheptylmethyl, cyclooctylmethyl, cyclononylmethyl, cyclodecylmethyl, cycloheptyl-1 -ethyl, cyclooctyl-1 -ethyl, cyclononyl-1 -ethyl, cyclode- cyl-1 -ethyl, cycloheptyl-2 -ethyl, cyclooctyl-2 -ethyl, cyclononyl-2 -ethyl, cyclodecylmethyl, cyclopropyl-1 -propyl, cyclopropyl-2-propyl, cyclopropyl-3-propyl, cyclobutyl-1 - propyl, cyclobutyl-2-propyl, cyclobutyl-3-prop
  • C3-C6-halocycloalkyl-Ci-C2-alkyl a Ci-C2-alkyl residue, as decribed above, wherein one of the hydrogen atoms is replaced by a Cs-C ⁇ -halocycloalkyl group.
  • Examples are 1- chlorocyclopropylmethyl, 1-chlorocyclobutylmethyl, 1-chlorocyclopentylmethyl, 1- chlorocyclohexylmethyl, 1-chlorocyclopropyl-i -ethyl, 1-chlorocyclobutyl-1 -ethyl, 1- chlorocyclopentyl-1 -ethyl, 1-chlorocyclohexyl-i -ethyl, 1-chlorocyclopropyl-2-ethyl, 1- chlorocyclobutyl-2 -ethyl, 1-chlorocyclopentyl-2-ethyl, 1-chlorocyclohexyl-2-ethyl, 2- chlorocyclopropylmethyl, 2-chlorocyclobutylmethyl, 2-chlorocyclopentylmethyl, 2- chlorocyclohexylmethyl, 2-chlorocyclopropyl-1 -ethyl, 2-chlorocyclobutyl-1 -eth
  • C3-Cio-halocycloalkyl-Ci-C4-alkyl is a Ci-C4-alkyl residue, as decribed above, wherein one of the hydrogen atoms is replaced by a C3-Cio-halocycloalkyl group.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • Ci-C 3 - Alkoxy is additionally, for example, n-propoxy or 1-methylethoxy (isopropoxy).
  • C1-C4- Alkoxy is additionally, for example, 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-ethyl butoxy, 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. C2-Cio-Alkoxy is like Ci-Cio-alkoxy with the exception of methoxy.
  • 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 OC2F5.
  • 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- C 2 F 5 , 1-(CH 2 F)-2-fluoroethoxy, 1-(CH 2 CI)-2-chloroethoxy, 1-(CH 2 Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
  • Ci-C ⁇ -Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy,
  • Alkenyloxy alkenyl as mentioned above which is attached via an oxygen atom, for ex- ample C2-Cio-alkenyloxy, such as 1-ethenyloxy, 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-1-butenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2- butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3
  • 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 C2-Cio-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
  • Haloalkynyloxy an alkynyloxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
  • Cycloalkoxy cycloalkyl 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, cyclononyloxy, cyclodecyloxy and the like;
  • Halocycloalkoxy a cycloalkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine.
  • Cycloalkenyloxy cycloalkenyl 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 10, 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, 1 to 4 or 1 to 3 carbon atoms, for example methoxymethyl, 2- methoxyethyl, ethoxymethyl, 3-methoxypropyl, 3-ethoxypropyl and the like.
  • Alkoxyalkoxy alkoxy as defined above having 1 to 10, 1 to 8, 1 to 6 or 1 to 4, in particu- lar 1 to 3, carbon atoms, in which one hydrogen atom is replaced by an alkoxy group having 1 to 8, 1 to 6 or in particular 1 to 4 carbon atoms, for example 2-methoxyethoxy, 2-ethoxyethoxy, 3-methoxypropoxy, 3-ethoxypropoxy and the like.
  • Alkylcarbonyl group of the formula R-CO- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, d-Cs-alkyl, d-C ⁇ -alkyl, Ci-C4-alkyl, Ci-C2-alkyl or C3- C4-alkyl. Examples are acetyl, propionyl and the like. Examples for C3-C4-alkylcarbonyl are propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, sec-butylcarbonyl, isobutylcar- bonyl and tert-butylcarbonyl.
  • Haloalkylcarbonyl group of the formula R-CO- in which R is a haloalkyl group as defined above, for example Ci-Cio-haloalkyl, d-Cs-haloalkyl, d-C ⁇ -haloalkyl, C1-C4- haloalkyl, Ci-C2-haloalkyl or C3-C4-haloalkyl. Examples are difluoromethylcarbonyl, trifluoromethylcarbonyl, 2,2-difluoroethylcarbony, 2,2,3-trifluoroethylcarbonyl and the like.
  • 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-C ⁇ -alkoxy, Ci-C4-alkoxy or C1-C2- alkoxy.
  • Ci-C4-alkoxycarbonyl are methoxycarbonyl, ethoxycarbonyl, pro- poxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, isobutoxy- carbonyl and tert-butoxycarbonyl.
  • Haloalkoxycarbonyl group of the formula R-CO- in which R is a haloalkoxy group as defined above, for example Ci-Cio-haloalkoxy, d-Cs-haloalkoxy, d-C ⁇ -haloalkoxy, Ci- C4-haloalkoxy or Ci-C2-haloalkoxy.
  • Ci-C4-haloalkoxycarbonyl are di- fluoromethoxycarbonyl, trifluoromethoxycarbonyl, 2,2-difluoroethoxycarbony, 2,2,3- trifluoroethoxycarbonyl and the like.
  • Alkylaminocarbonyl group of the formula R-NH-CO- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-C 8 -alkyl, d-Ce-alkyl, Ci-d-alkyl, C1-C2- alkyl or C3-d-alkyl.
  • Ci-C4-alkylaminocarbonyl are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, butylaminocar- bonyl, sec-butylaminocarbonyl, isobutylaminocarbonyl and tert-butylaminocarbonyl.
  • Dialkylaminocarbonyl group of the formula RR'N-CO- in which R and R', independently of each other, are an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs- alkyl, Ci-C 6 -alkyl, Ci-d-alkyl, Ci-C 2 -alkyl or C 3 -C 4 -alkyl.
  • R and R' independently of each other, are an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-Cs- alkyl, Ci-C 6 -alkyl, Ci-d-alkyl, Ci-C 2 -alkyl or C 3 -C 4 -alkyl.
  • Examples for di-(Ci-d-alkyl)- aminocarbonyl are dimethylaminocarbonyl, diethylaminocarbonyl, dipropylaminocar- bonyl, diisopropylaminocarbonyl and dibutyla
  • Aminoalkyl group of the formula R-NH2 in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-C 8 -alkyl, Ci-C 6 -alkyl, Ci-C 4 -alkyl, Ci-C 2 -alkyl or C 3 -C 4 - alkyl.
  • R is an alkyl group as defined above, for example Ci-Cio-alkyl, Ci-C 8 -alkyl, Ci-C 6 -alkyl, Ci-C 4 -alkyl, Ci-C 2 -alkyl or C 3 -C 4 - alkyl.
  • Examples are aminomethyl, 1- and 2-aminoethyl, 1-, 2- and 3-aminopropyl, 1- and 2-amino1-methylethyl, 1-, 2-, 3- and 4-aminobutyl and the like.
  • Alkylsulfonyl group of the formula R-S(O)2- in which R is an alkyl group as defined above, for example Ci-Cio-alkyl, d-Cs-alkyl, Ci-C6-alkyl, Ci-C4-alkyl or Ci-C2-alkyl.
  • Examples for d-d-alkylsulfonyl are methylsulfonyl, ethylsulfonyl, propylsulfonyl, iso- propylsulfonyl, n-butylsulfonyl, sec-butylsulfonyl, isobutylsulfonyl and tert-butylsulfonyl.
  • Alkylthio alkyl as defined above which is attached via a sulfur atom.
  • Haloalkylthio haloalkyl as defined above which is attached via a sulfur atom.
  • Alkenylthio alkenyl as defined above which is attached via a sulfur atom.
  • Haloalkenylthio haloalkenyl as defined above which is attached via a sulfur atom.
  • Alkynylthio alkynyl as defined above which is attached via a sulfur atom.
  • Haloalkynylthio haloalkynyl as defined above which is attached via a sulfur atom.
  • Cycloalkylthio cycloalkyl as defined above which is attached via a sulfur atom.
  • Aryl is a carbocyclic aromatic monocyclic or polycyclic ring containing 6 to 16 carbon atoms as ring members. Examples are phenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl and azulenyl. Preferably, aryl is phenyl or naphthyl, and especially phenyl.
  • Phenyl-Ci-C4-alkyl Ci-C4-alkyl (as defined above), where a hydrogen atom is replaced by a phenyl group, such as benzyl, phenethyl and the like.
  • Phenyl-Ci-C4-alkoxy Ci-C4-alkoxy (as defined above), where one hydrogen atom is replaced by a phenyl group, such as benzyloxy, phenethyloxy and the like.
  • a seven-membered saturated or partially unsaturated heterocycle which contains one, two or three 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 ni- trogen 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
  • Linear C2-alkylene divalent unbranched chains having 2 carbon atoms, namely CH 2 CH 2 .
  • Linear C 2 - or C3-alkylene divalent unbranched chains having 2 or 3 carbon atoms, namely CH 2 CH 2 and CH 2 CH 2 CH 2 .
  • Linear d-Cs-alkylene divalent unbranched chains having 1 to 5 carbon atoms, namely CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 and CH 2 CH 2 CH 2 CH 2 CH 2 .
  • C 2 -C5-Alkylene divalent branched or preferably unbranched chains having 2 to 5 carbon atoms, for example 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 .
  • C4-C5-Alkylene divalent branched or preferably unbranched chains having 4 to 5 carbon atoms, for example CH 2 CH 2 CH 2 CH 2 or CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 .
  • the group -SM is more correctly spoken a group -S " M + , where M + is a metal cation equivalent or an ammonium cation as defined above.
  • M + is a metal cation equivalent or an ammonium cation as defined above.
  • a metal cation equivalent is more correctly spoken 1/a M a+ , where a is the valence of the metal and is in general 1 , 2 or 3.
  • Ar if it is a heterocyclic ring as defined above, is bound via a C-atom to the group Y.
  • Ar is phenyl which may carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, substituents R 2 , or is a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heteroaromatic ring may carry 1 , 2, 3 or 4, preferably 1 , 2 or 3, more preferably 1 or 2, substituents R 3 .
  • Ar preferably is phenyl which may carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, substituents R 2 , or is a 5- or 6-membered heteroaromatic ring containing 1 heteroatom selected from N, O and S and optionally 1 or 2 further nitrogen atoms as ring members, where the heteroaromatic ring may carry 1 , 2, 3 or 4, preferably 1 or 2, substituents R 3 .
  • Suitable 5- or 6-membered heteroaromatic radicals are listed above.
  • pyridyl such as pyridin-2-yl, pyridin-3-yl or pyridin-4-yl
  • pyrimidyl such as 2-pyrimidinyl, 4-pyrimidinyl or 5-pyrimidinyl
  • furyl such as 2-furyl or 3-furyl
  • thienyl such as 2-thienyl or 3-thienyl
  • pyr- rolyl such as 1-pyrrolyl, 2-pyrrolyl or 3-pyrrolyl, especially 2-pyrrolyl or 3-pyrrolyl, pyra- zolyl, such as 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl or 5-pyrazolyl, especially 3-pyrazolyl, 4-pyrazolyl or 5-pyrazolyl, imidazolyl, such as 1-imidazolyl, 2-imidazolyl or 4-imidazolyl, especially 2-imidazolyl or 4-imidazolyl, imidazolyl, such as 1-imidazolyl,
  • the given binding position is relative to the 1 -position of the one ring heteroatom.
  • the given binding position is relative to the 1- and 2-positions of the 2 nitrogen ring atoms, in imidazolyl, it is relative to the 1- and 3-positions of the 2 nitrogen ring atoms, in oxazolyl, it is relative to the 1 -position of the oxygen ring atom and to the 3-position of the nitrogen ring atom, in isoxazolyl, it is relative to the 1- position of the oxygen ring atom and to the 2-position of the nitrogen ring atom, in thiazolyl, it is relative to the 1 -position of the sulfur ring atom and to the 3-position of the nitrogen ring atom, in isothiazolyl, it is relative to the 1 -position of the sulfur ring atom and to the 2-position of the nitrogen ring atom, etc.
  • Ar is phenyl which may carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, substituents R 2 , or is a 5- or 6-membered heteroaromatic ring selected from pyridyl, such as pyridin-2-yl, pyridin-3-yl or pyridin-4-yl, thienyl, such as 2- or 3-thienyl, and thiazolyl, such as 2-thiazolyl, 4-thiazolyl or 5-thiazolyl.
  • pyridyl such as pyridin-2-yl, pyridin-3-yl or pyridin-4-yl
  • thienyl such as 2- or 3-thienyl
  • thiazolyl such as 2-thiazolyl, 4-thiazolyl or 5-thiazolyl.
  • pyridyl such as pyridin-2-yl, pyridin-3-yl or pyridin-4-yl, and especially to pyridin-2-yl, where the heteroaromatic ring may carry 1 , 2, 3 or 4, preferably 1 ,
  • substituents R 3 2 or 3, more preferably 1 or 2, substituents R 3 .
  • Ar is a 6-membered heteroaromatic ring, this carries preferably O, 1 , 2 or 3, more preferably 0, 1 or 2, substituents R 3 ,where the two or more substituents R 3 may be the same or different.
  • Ar is a 5-membered heteroaromatic ring, this carries preferably 0, 1 or 2 substituents R 3 , where two substituents R 3 may be the same or different.
  • R 2 is preferably selected from halogen, OH, SH, NO 2 , CN, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy, and Ci-C 4 - haloalkoxy, more preferably from fluorine, chlorine, bromine, Ci-C 4 -alkyl, Ci-C 4 - haloalkyl, Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy, even more preferably from fluorine, chlorine, bromine, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3, and in particular from fluorine, chlorine, bromine, CH3, CF3, OCH3 and OCF3.
  • R 3 may be C- or N-bound, but is preferably bound to a C-atom of Ar.
  • R 3 is preferably selected from halogen, OH, SH, NO 2 , CN, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy, and CrC 4 - haloalkoxy, more preferably from fluorine, chlorine, bromine, Ci-C 4 -alkyl, CrC 4 - haloalkyl, Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy, even more preferably from fluorine, chlorine, bromine, CH3, CHF 2 , CF3, OCH3, OCHF 2 and OCF3, and in particular from fluorine, chlorine, bromine, CH3, CF3, OCH3 and OCF3.
  • Ar is selected from following formulae Ar.1 to Ar.50, where in formula Ar.1 , the combination of the variables R 21 , R 22 , R 23 , R 24 and R 25 is selected from the defini- tion given in each line of Table A below.
  • Het is bound via two ring C-atoms to the group Y and the quaternary carbon atom (carrying the ketal group and the triazolylmethyl group).
  • Het is a (divalent) 5- or 6-membered het- eroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heteroaromatic ring may carry 1 , 2, 3 or 4, preferably 1 or 2, sub- stituents R 4 . More precisely spoken, Het preferably is a 5- or 6-membered heteroaromatic ring containing 1 heteroatom selected from N, O and S and optionally 1 or 2 further nitrogen atoms as ring members, where the heteroaromatic ring may carry 1 , 2, 3 or 4, preferably 1 or 2, substituents R 4 . Suitable 5- or 6-membered heteroaromatic radicals are listed above.
  • pyridylene such as 2,3-pyridylene, 2,4-pyridylene, 2,5-pyridylene, 2,6-pyridylene, 3,4-pyridylene or 3,5- pyridylene
  • pyrimidylene such as 2,4-pyrimidylene, 2,5-pyrimidylene, 4,5-pyrimidylene or 4,6-py ⁇ imidylene
  • furylene such as 2,3-furylene, 2,4-furylene, 2,5-furylene or 3,4- furylene
  • thienyl such as 2,3-thienylene, 2,4-thienylene, 2,5-thienylene or 3,4- thienylene
  • pyrrolyl such as 1 ,2-pyrrolylene, 1 ,3-pyrrolylene, 2,3-pyrrolylene, 2,4- pyrrolylene, 2,5-pyrrolylene or 3,4
  • the given binding positions are to be understood as relative to the 1 -position of the ring heteroatom with the highest priority.
  • the given binding position is relative to the 1 -position of the one ring heteroatom.
  • the given bind- ing position is relative to the 1- and 2-positions of the 2 nitrogen ring atoms, in imida- zolylene, it is relative to the 1- and 3-positions of the 2 nitrogen ring atoms, in oxazolylene, it is relative to the 1 -position of the oxygen ring atom and to the 3-position of the nitrogen ring atom, in isoxazolylene, it is relative to the 1 -position of the oxygen ring atom and to the 2-position of the nitrogen ring atom, in thiazolylene, it is relative to the 1 -position of the sulfur ring atom and to the 3-position of the nitrogen ring atom, in isothiazolylene, it is relative to the 1 -position of the sulfur ring atom and to the 3-position of the nitrogen ring atom
  • pyridylene especially 2,5- or 3,6-pyridylene, thienylene, especially 2,4- or 2,5-thienylene, and thiazolylene, especially 2,4-thiazolylene or 2,5- thiazolylene.
  • pyridylene especially 2,5- or 3,6-pyridylene, thienylene, especially 2,4- or 2,5-thienylene.
  • pyridylene especially to 2,5- or 3,6-pyridylene.
  • Het is a 6-membered heteroaromatic ring, this carries preferably 0, 1 , 2 or 3, more preferably 0, 1 or 2, substituents R 4 ,where the two or more substituents R 4 may be the same or different.
  • Het is a 5-membered heteroaromatic ring, this carries preferably 0, 1 or 2 substituents R 4 , where two substituents R 4 may be the same or different.
  • R 4 may be C- or N-bound, but is preferably bound to a C-atom of Het.
  • R 4 is preferably selected from halogen, OH, SH, NO 2 , CN, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy, and CrC 4 - haloalkoxy, more preferably from fluorine, chlorine, bromine, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, even more preferably from fluorine, chlorine, bromine, CH3, CHF2, CF3, OCH3, OCHF2 and OCF3, particularly preferably from fluorine, chlorine, bromine, CH3, CF3, OCH3 and OCF3, and specifically from fluorine and chlorine.
  • Het is selected from following formulae Het.1 to Het.16, where # is the attachment point to the quaternary carbon atom (which carries the ketale and the tria- zolylmethyl group) and * is the attachment point to the group Y:
  • R 8 is specifically Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl, preferably methyl, or is Ci-C4-alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy, preferably methoxy, and is more specifically methyl, and in the group -S(O) 2 R 8 , R 8 is specifically methyl.
  • R 13 is hydrogen and R 14 is selected from hydrogen, Ci-C4-alkyl and phenyl, preferably from hydrogen and Ci-C4-alkyl; or R 13 and R 14 are both Ci-C4-alkyl, preferably methyl or ethyl.
  • M is preferably selected from an alkali metal cation, an earth alkaline metal cation equivalent, a cation equivalent of Cu, Zn, Fe or Ni or an ammonium cation of formula (NR a R b R c R d ) + , wherein one of R a , R b , R c and R d is hydrogen and three of R a , R b , R c and R d , independently of each other, are selected from Ci-Cio-alkyl.
  • M is selected from Li + , Na + , K + , YiMg 2+ , a cation equivalent of Cu, Zn, Fe or Ni and an ammonium cation of formula (NR a R b R c R d ) + , wherein one of R a , R b , R c and R d is hydrogen and three of R a , R b , R c and R d , independently of each other, are selected from C1-C10- alkyl.
  • M is selected from Na + , K + , /4Mg 2+ , /4Cu 2+ , /4Zn 2+ , /4Fe 2+ , /4Ni 2+ , triethylammonium and trimethylammonium.
  • R 1 is selected from hydrogen, methyl, ethyl, propyl, isopropyl, methylcarbonyl, methoxycarbonyl,
  • R 1 is hydrogen, methyl, methylcarbonyl, methoxycarbonyl, Na + or a group of the formula III.
  • Y is preferably O.
  • A is preferably a linear C2- or C3-alkyene bridge, where 1 or 2 hydrogen atoms of the alkylene bridge may be replaced by 1 or 2 substituents R 5 , where each R 5 is independently selected from Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4- alkoxy and Ci-C4-haloalkoxy, and preferably from methyl, ethyl, methoxy, ethoxy and methoxymethoxy, or two substituents R 5 bound on adjacent carbon atoms, together with the carbon atoms to which they are bound, form a cyclopentyl or cyclohexyl ring.
  • A is a linear C2- or C3-alkyene bridge, where 1 hydrogen atom of the alkylene bridge may be replaced by 1 substituent R 5 , where R 5 is Ci-C4-alkyl. Even more preferably, A is a linear C2-alkyene bridge, where 1 hydrogen atom of the al- kylene bridge may be replaced by 1 substituent R 5 , where R 5 is Ci-C4-alkyl and preferably methyl. Specifically, A is -CH(CHs)-CH 2 -.
  • m is preferably 0 or 2 and more preferably 0.
  • Examples for preferred compounds I and Il are compounds of formulae 1.1 to 1.192 and 11.1 to 11.96, where the variables have one of the general or, in particular, one of the preferred meanings given above.
  • Examples of preferred compounds are the individual compounds compiled in the tables 1 to 70992 below. Moreover, the meanings mentioned below 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.
  • Tables 197 to 245 Compounds of the formula 1.1 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A, R 1 is as defined in any of tables 1 to 49 and Het is a radical of formula Het.5
  • Tables 295 to 343 Compounds of the formula 1.1 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A, R 1 is as defined in any of tables 1 to 49 and Het is a radical of formula Het.7
  • Tables 344 to 392 Compounds of the formula 1.1 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A, R 1 is as defined in any of tables 1 to 49 and Het is a radical of formula Het.8
  • Tables 589 to 637 Compounds of the formula 1.1 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A, R 1 is as defined in any of tables 1 to 49 and Het is a radical of formula Het.13
  • R 1 and Het is as defined in any of tables 1 to 784 Tables 1569 to 2352
  • R 1 and Het is as defined in any of tables 1 to 784
  • Tables 2353 to 3136 Compounds of the formula 1.4 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of
  • R 1 and Het is as defined in any of tables 1 to 784
  • R 6 and Het is as defined in any of tables 1 to 784
  • R 1 and Het is as defined in any of tables 1 to 784 Tables 5489 to 6272
  • R 1 and Het is as defined in any of tables 1 to 784
  • Tables 6273 to 7056 Compounds of the formula 1.9 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of
  • R 1 and Het is as defined in any of tables 1 to 784
  • Tables 7841 to 8624 Compounds of the formula 1.11 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1 and Het is as defined in any of tables 1 to 784
  • Tables 8625 to 9408 Compounds of the formula 1.12 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1 and Het is as defined in any of tables 1 to 784
  • Tables 12545 to 13328 Compounds of the formula 1.17 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1 and Het is as defined in any of tables 1 to 784
  • Tables 17249 to 18032 Compounds of the formula 1.23 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1 and Het is as defined in any of tables 1 to 784
  • Tables 21 169 to 21952 Compounds of the formula 1.28 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1 and Het is as defined in any of tables 1 to 784
  • Tables 22737 to 23520 Compounds of the formula 1.30 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1 and Het is as defined in any of tables 1 to 784
  • Tables 23521 to 24304 Compounds of the formula 1.31 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1 and Het is as defined in any of tables 1 to 784
  • Tables 27441 to 28224 Compounds of the formula 1.36 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1 and Het is as defined in any of tables 1 to 784
  • Tables 32145 to 32928 Compounds of the formula 1.42 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1 and Het is as defined in any of tables 1 to 784
  • Tables 36065 to 36848 Compounds of the formula 1.47 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1 and Het is as defined in any of tables 1 to 784
  • Tables 37665 to 37680 Compounds of the formula 1.51 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 37697 to 37712 Compounds of the formula 1.53 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 37713 to 37728 Compounds of the formula 1.54 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 37793 to 37808 Compounds of the formula 1.59 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 37889 to 37904 Compounds of the formula 1.65 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 37969 to 37984 Compounds of the formula 1.70 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 38001 to 38016 Compounds of the formula 1.72 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 38017 to 38032 Compounds of the formula 1.73 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 38097 to 38112 Compounds of the formula 1.78 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 38193 to 38208 Compounds of the formula 1.84 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 38273 to 38288 Compounds of the formula 1.89 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 38305 to 38320 Compounds of the formula 1.91 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 38321 to 38336 Compounds of the formula 1.92 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and Het is as defined in any of tables 37633 to 37648
  • Tables 38401 to 38449 Compounds of the formula 1.97 in which the combination of Het and Ar' for a compound corresponds in each case to one row of Table B and R 1 is as defined in any of tables 1 to 49
  • Tables 40838 to 40874 Compounds of the formula 11.1 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A, R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.2
  • R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.3
  • R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.4
  • R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.5 Tables 40986 to 41022
  • R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.6
  • Tables 41023 to 41059 Compounds of the formula 11.1 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A, R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.7
  • R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.8
  • Tables 41097 to 41 133 Compounds of the formula 11.1 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A, R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.9
  • Tables 41 134 to 41 170 Compounds of the formula 11.1 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A, R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.10
  • R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.11
  • R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.12
  • R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.14
  • Tables 41319 to 41355 Compounds of the formula 11.1 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A, R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.15
  • R 1a is as defined in any of tables 40800 to 40837 and Het is a radical of formula Het.16
  • R 1a and Het is as defined in any of tables 40800 to 41392 Tables 42577 to 43168
  • R 1a and Het is as defined in any of tables 40800 to 41392 Tables 43169 to 43760
  • R 1a and Het is as defined in any of tables 40800 to 41392
  • R 1a and Het is as defined in any of tables 40800 to 41392
  • R 1a and Het is as defined in any of tables 40800 to 41392
  • R 1a and Het is as defined in any of tables 40800 to 41392 Tables 46129 to 46720
  • Tables 46721 to 47312 Compounds of the formula 11.1 1 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1a and Het is as defined in any of tables 40800 to 41392
  • Tables 47905 to 48496 Compounds of the formula 11.13 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1a and Het is as defined in any of tables 40800 to 41392
  • Tables 48497 to 49088 Compounds of the formula 11.14 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1a and Het is as defined in any of tables 40800 to 41392
  • Tables 51457 to 52048 Compounds of the formula 11.19 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1a and Het is as defined in any of tables 40800 to 41392
  • Tables 55009 to 55600 Compounds of the formula 11.25 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1a and Het is as defined in any of tables 40800 to 41392
  • Tables 57969 to 58560 Compounds of the formula 11.30 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1a and Het is as defined in any of tables 40800 to 41392
  • Tables 59153 to 59744 Compounds of the formula 11.32 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1a and Het is as defined in any of tables 40800 to 41392
  • Tables 59745 to 60336 Compounds of the formula 11.33 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1a and Het is as defined in any of tables 40800 to 41392
  • Tables 62705 to 63296 Compounds of the formula 11.38 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1a and Het is as defined in any of tables 40800 to 41392
  • Tables 66257 to 66848 Compounds of the formula 11.44 in which the combination of R 21 , R 22 , R 23 , R 24 and R 25 for a compound corresponds in each case to one row of Table A and the combination of R 1a and Het is as defined in any of tables 40800 to 41392
  • Tables 69217 to 69253 Compounds of the formula 11.49 in which the combination of Het and Ar' for a compound corresponds in each case to one row of Table B and R 1a is as defined in any of tables 40800 to 40837
  • Tables 69291 to 69327 Compounds of the formula 11.51 in which the combination of Het and Ar' for a compound corresponds in each case to one row of Table B and R 1a is as defined in any of tables 40800 to 40837 Tables 69328 to 69364 Compounds of the formula 11.52 in which the combination of Het and Ar' for a compound corresponds in each case to one row of Table B and R 1a is as defined in any of tables 40800 to 40837 Tables 69365 to 69401 Compounds of the formula 11.53 in which the combination of Het and Ar' for a com- pound corresponds in each case to one row of Table B and R 1a is as defined in any of tables 40800 to 40837 Tables 69402 to 69438
  • radicals Ar.2 to Ar.50 correspond to the radicals listed above as specific embodiments of Ar as groups of formulae Ar.2 to Ar.50
  • radicals Het.1 to Het.16 correspond to the radicals listed above as specific embodiments of Het as groups of formulae Het.1 to Het.16.
  • the radicals Ar.2 to Ar.50 correspond to the radicals listed above as specific embodiments of Ar as groups of formulae Ar.2 to Ar.50.
  • the radicals Het.1 to Het.16 correspond to the radicals listed above as specific embodiments of Het as groups of formulae Het.1 to Het.16.
  • an organolithium base such as n-butyllithium, tert- butyllithium or sec-butyllithium, lithium diisopropyl amide, sodium hydride, sodium amide or potassium tert-butylate mixed with tetramethylethylene diamine (TMEDA), and then the resulting anion is reacted with elemental sulfur.
  • Sulfur is generally used in powdered form.
  • the reaction is generally carried out in an inert solvent, such as ethers, e.g. diethylether, methyl-tert-butylether, tetrahydrofuran or dioxane, dimethoxyethane, liquid ammonia, dimethylsulfoxide or dimethylformamide.
  • the reaction temperature is not very critical and can range, for example, from -70 to +50 0 C, preferably from -70 to 0 0 C.
  • sulfurization can be carried out in the absence of a base by reacting 7 with elemental sulfur in a high-boiling solvent, such as N-methylpyrrolidinone, diox- ane or N,N-dimethylformamide, while heating, e.g. to 160 to 250 0 C.
  • a high-boiling solvent such as N-methylpyrrolidinone, diox- ane or N,N-dimethylformamide
  • the resulting mixture is hydrolyzed, e.g. by the addition of water or an aqueous acid, such as a mineral acid (e.g. dilute sulfuric acid or hydrochloric acid), acetic acid or ammoniumchloride, to give compound I.
  • a high-boiling solvent such as N-methylpyrrolidinone, diox- ane or N
  • the triazole compound IV can be prepared in analogy to known methods, such as described, for example, in EP-A-0065485, as outlined in scheme 2.
  • the compound 1 wherein X is a good leaving group, such as a halogen atom, in particular Cl, Br or I, phenylsulfonyloxy, p-tosyloxy, trifluoroacetyloxy or alkylsulfonyloxy, such as mesyloxy, can be reacted with the [1 ,2,4]-1 H-triazole compound 2, wherein M is a hydrogen atom or a metal atom, in particular an alkali metal atom, such as Li, Na or K.
  • M is a hydrogen atom or a metal atom, in particular an alkali metal atom, such as Li, Na or K.
  • the reaction is suitably carried out in the presence of a base, such as an alkali metal hydride (e.g. sodium hydride, potassium hydride), an alkali metal hydroxide (e.g. sodium hydroxide, potassium hydroxide), an alkali metal carbonate (e.g. sodium carbonate, potassium carbonate, caesium carbonate) or a suitable amine (e.g. triethyl- amine, triethylenediamine, piperidine, pyridine, 4-dimethylaminopyridine, 4- pyrrolidylpyridine).
  • a base such as an alkali metal hydride (e.g. sodium hydride, potassium hydride), an alkali metal hydroxide (e.g. sodium hydroxide, potassium hydroxide), an alkali metal carbonate (e.g. sodium carbonate, potassium carbonate, caesium carbonate) or a suitable amine (e.g. triethyl- amine, triethylenediamine, piperidine
  • the reaction is suitably carried out in a solvent.
  • Suitable solvents are inert versus the reacants and products and are rather polar, for example, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, acetoni- trile, benzonitrile, ethers, such as diethyl ether, dipropyl ether, methyl-tert-butyl ether, tetrahydrofuran or dioxane, and the like, and can be used in combination with other inert, less polar solvents, such as benzene, toluene, the xylenes, chlorobenzene, nitrobenzene, hexane, heptane, petrolether and the like.
  • the reaction temperature is not very critical and can range, for example from 0 to 220 0 C and preferably from 80 to 170 0 C.
  • the reaction is carried out at reflux temperature of the reaction mixture.
  • Compound 1 in turn can be prepared in analogy to known methods, such as described, for example, in EP-A-0065485 or in Synthesis, 1974, I, 23, as outlined in scheme 3 below.
  • the ketone 3 may be reacted with a diol HO-A-OH for several hours preferably in the presence of an azeotrope-forming compound, such as benzene, toluene, xylene, chloroform or tetrachloromethane, which can also serve as reaction solvents.
  • the ketalization reaction is accelerated by the presence of a strong acid, such p-toluoenesulfonic acid.
  • halogenation of the resulting ketale 4 yields ketale 1 , wherein X is a halogen atom, which, if desired, can be converted into a compound 1 , wherein X is a leaving group X other than halogen.
  • the ketone 3 can be obtained in analogy to known methods, such as described, for example, in EP-A-0065485, from the condensation of compounds 5 and 6, wherein X 1 is a group Y-H or Y-M, wherein M is a metal atom, in particular an alkali metal atom, such as Li, Na or K, and X 2 is a good leaving group, such as a halogen atom, such as F, Cl, Br or I, phenylsulfonyloxy, p-tosyloxy, trifluoroacetyloxy or alkylsulfonyloxy, such as mesyloxy, or, vice versa, wherein X 1 is a good leaving group and X 2 is a group Y-H or Y-M, as outlined in scheme 4 below.
  • M is a metal atom, in particular an alkali metal atom, such as Li, Na or K
  • X 2 is a good leaving group, such as a
  • X 1 or X 2 is Y-H
  • the reaction is suitably carried out in the presence of a base, such as an alkali metal hydride (e.g. sodium hydride, potassium hydride), an alkali metal hydroxide (e.g. sodium hydroxide, potassium hydroxide), an alkali metal carbonate (e.g. sodium carbonate, potassium carbonate, caesium carbonate) or a suitable amine (e.g. triethylamine, triethylenediamine, piperidine, pyridine, 4-dimethylaminopyridine, 4-pyrrolidylpyridine).
  • a base such as an alkali metal hydride (e.g. sodium hydride, potassium hydride), an alkali metal hydroxide (e.g. sodium hydroxide, potassium hydroxide), an alkali metal carbonate (e.g. sodium carbonate, potassium carbonate, caesium carbonate) or a suitable amine (e.g. triethylamine,
  • the reaction can be accelerated by the addition of an alkali metal iodide, such as NaI or Kl.
  • the reaction is suitably carried out in a solvent.
  • Suitable sol- vents are inert versus the reacants and products and are rather polar, for example, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, acetonitrile, ben- zonitrile, ethers, such as diethyl ether, dipropyl ether, methyl-tert-butyl ether, tetrahy- drofuran or dioxane, and the like, and can be used in combination with other inert, less polar solvents, such as benzene, toluene, the xylenes, chlorobenzene, nitrobenzene, hexane, heptane, petrolether and the like.
  • the reaction temperature such as benzene, tol
  • This in turn can be prepared from the hydroxyl compound 8 which is reacted with a difunctional derivative 9 of carbonic acid, such as phosgene, a halogenoformic acid diester, a dialkylcarbonic diester or a diphenylcarbonic acid diester and further reaction with the hydroxyl compound 10.
  • Decarboxylation is carried out by heating 7 in substance or in a high-boiling inert solvent, such as diphenylether or ethyleneglycoldimethylether, to a temperature in the range of from 120 to 220°C.
  • compound IV can be prepared in analogy to the method described in EP-A-0065485 as outlined in scheme 6 below by a ketalization reaction of the ketone 11 with a diol HO-A-OH.
  • the ketalization reaction can be carried out under reaction conditions described for scheme 3.
  • the ketone 11 in turn can be prepared in analogy to the method described in EP-A- 0065485 as outlined in scheme 7 below by reacting the compound 12, wherein X is a good leaving group, such as a halogen atom, in particular Cl, Br or I, phenylsulfonyloxy, p-tosyloxy, trifluoroacetyloxy or alkylsulfonyloxy, such as mesyloxy, with the triazole compound 2 under reaction conditions described for the reaction in scheme 2.
  • Compound 12, in turn, can be obtained from the halogenation of the ketone 3.
  • compound IV can be prepared in analogy to the method described in EP-A-0065485 as outlined in scheme 8 below by condensation of compounds 13 and 14, wherein X 1 is a group Y-H or Y-M, wherein M is a metal atom, in particular an alkali metal atom, such as Li, Na or K, and X 2 is a good leaving group, such as a halogen atom, in particular Cl, Br or I, phenylsulfonyloxy, p- tosyloxy, trifluoroacetyloxy or alkylsulfonyloxy, such as mesyloxy, or, vice versa, wherein X 1 is a good leaving group and X 2 is a group Y-H or Y-M, under reaction conditions as described for scheme 4.
  • M is a metal atom, in particular an alkali metal atom, such as Li, Na or K
  • X 2 is a good leaving group, such as a halogen atom, in
  • the carbonic ester 15, in turn, can be prepared under reaction conditions described for the condensation reaction in scheme 5.
  • radicals in the above reactants if inert towards the respective reaction, can be present in the above reaction steps or can be introduced at a later stage, e.g. into compound IV.
  • Suitable bases are, for example, alkali metal hydrides (e.g. sodium hydride, potassium hydride), alkali metal hydroxides (e.g. sodium hydroxide, potassium hydroxide), alkali metal carbonates (e.g. sodium carbonate, potassium carbonate, caesium carbonate), alkali metal alkoxides (e.g. sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide) or organolithium bases (e.g.
  • alkali metal hydrides e.g. sodium hydride, potassium hydride
  • alkali metal hydroxides e.g. sodium hydroxide, potassium hydroxide
  • alkali metal carbonates e.g. sodium carbonate, potassium carbonate, caesium carbonate
  • alkali metal alkoxides e.g. sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, potassium
  • n-butyl lithium, sec-butyl lithium, tert-butyl lithium and lithium diisopropylamine. The reaction is generally carried out in a suitable solvent.
  • suitable solvents are, for example, toluene, N-methylpyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane), acetonitrile, N,N-dimethylformamide or dimethylsulfox- ide.
  • compounds of formula I wherein m is 0 and R 1 is Ci-Cio-alkyl, C1-C10- haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-Cio-alkynyl, C2-Cio-haloalkynyl, C3-C10- cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenyl-Ci-C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may be substituted as described above, and a 5- or 6- membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, where the heterocyclic ring may be substituted as described above, may be prepared in analogy to the method described in Heterocycles, 23(7), 1645-1649, 1985 by react
  • alkoxide e.g. methoxide, ethoxide
  • pentafluorophenoxide in the presence of a base.
  • bases are, for example, alkali metal hydrides (e.g. sodium hydride, potassium hydride), alkali metal hydroxides (e.g. sodium hydroxide, potassium hydroxide), alkali metal carbonates (e.g. sodium carbonate, potassium carbonate, caesium carbonate), alkali metal alkoxides (e.g. sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide) or organolithium bases (e.g.
  • alkali metal hydrides e.g. sodium hydride, potassium hydride
  • alkali metal hydroxides e.g. sodium hydroxide, potassium hydroxide
  • alkali metal carbonates e.g. sodium carbonate, potassium carbonate, caesium carbonate
  • n-butyl lithium, sec-butyl lithium, tert-butyl lithium, lithium diisopropylamine The reaction is generally carried out in a suitable solvent.
  • suitable solvents are, for example, toluene, N- methylpyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2- dimethoxyethane), acetonitrile, N,N-dimethylformamide or dimethylsulfoxide.
  • Compounds of formula I, wherein m is 0 and R 1 is -SO2R 8 may be prepared in analogy to the method described in DE-A-19620590 by reacting a compound I, wherein m is 0 and R 1 is H, with a compound R 8 -SC"2-W, wherein R 8 has one of the above meanings and W is a good leaving group, such as a halide (e.g. Cl, Br, I), an alkoxide (e.g. methoxide, ethoxide) or pentafluorophenoxide, in the presence of a base.
  • Suitable bases are, for example, alkali metal hydrides (e.g.
  • alkali metal hydroxides e.g. sodium hydroxide, potassium hydroxide
  • alkali metal carbon- ates e.g. sodium carbonate, potassium carbonate, caesium carbonate
  • alkali metal alkoxides e.g. sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide
  • organolithium bases e.g. n-butyl lithium, sec- butyl lithium, tert-butyl lithium, lithium diisopropylamine.
  • Suitable solvents are, for example, toluene, N- methylpyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2- dimethoxyethane), acetonitrile, N,N-dimethylformamide or dimethylsulfoxide.
  • Compounds of formula I, wherein m is 0 and R 1 is -CN may be prepared in analogy to the method described in DE-A-19620407 by reacting a compound I, wherein m is 0 and R 1 is H, with a compound CN-W, wherein W is a good leaving group, such as a halide (e.g. Cl, Br, I), in the presence of a base.
  • Suitable bases are, for example, alkali metal hydrides (e.g. sodium hydride, potassium hydride), alkali metal hydroxides (e.g. sodium hydroxide, potassium hydroxide), alkali metal carbonates (e.g.
  • reaction is generally carried out in a suitable solvent.
  • suitable solvents are, for example, toluene, N-methylpyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane), acetonitrile, N,N-dimethylformamide or dimethylsulfoxide.
  • Compounds of formula I, wherein m is 0 and R 1 is M may be prepared in analogy to the method described in DE-A-19617282 by reacting a compound I, wherein m is 0 and R 1 is H, with an amine NR a R b R c , wherein R a , R b and R c are as defined above, or with a metal salt, such as sodium hydroxide, potassium hydroxide or copper acetate.
  • a metal salt such as sodium hydroxide, potassium hydroxide or copper acetate.
  • Suitable bases are, for example, alkali metal hydrides (e.g. sodium hydride, potassium hydride), alkali metal hydroxides (e.g. sodium hydroxide, potassium hydroxide), alkali metal carbonates (e.g. sodium carbonate, potassium carbonate, caesium carbonate), alkali metal alkoxides (e.g.
  • organolithium bases e.g. n-butyl lithium, sec-butyl lithium, tert-butyl lithium, lithium diisopropylamine.
  • the reaction is generally carried out in a suitable solvent. Suitable solvents are, for example, toluene, N-methylpyrrolidinone, ethers (e.g. diethyl ether, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane), acetonitrile, N,N-dimethylformamide or dimethylsulfoxide.
  • Compounds I, wherein m is 1 or 2 can be prepared from respective compounds I, wherein m is 0, by oxidation.
  • compounds I, wherein m is 2 can be prepared from compounds IV by first deprotonating the triazolyl ring and then reacting with a sulfonyl chloride R 1 S ⁇ 2CI.
  • Compounds I, wherein m is 3, can be prepared from compounds IV by first deprotonating the triazolyl ring and then reacting with sulfuric acid chloride or a sulfuric ester chloride of formula R 1 OS ⁇ 2CI, wherein R 1 is selected from hydrogen, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio-alkenyl, C2-Cio-haloalkenyl, C2-C10- alkynyl, C2-Cio-haloalkynyl, C3-Cio-cycloalkyl, C3-Cio-halocycloalkyl, phenyl, phenyl-Ci- C4-alkyl, where the phenyl moiety in the 2 last-mentioned radicals may be substituted as mentioned above, and a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S
  • reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or silica gel.
  • Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils, which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or digestion.
  • a further aspect of the invention relates to compounds of formula IV
  • Ar, Het, A and Y have one of the general or, in particular, one of the preferred meanings given above for compounds I and II.
  • Particularly preferred compounds IV are compounds of formulae IV.1 to IV.48, wherein the combination of R 21 , R 22 , R 23 , R 24 and R 25 corresponds in each case to one row in table A above and Het has in ech case one of the formulae Het.1 to Het.16, and compounds of formulae IV.49 to IV.96, wherein the combination of Het and Ar' corresponds in each case to one row in table B above.
  • the invention further refers to an agricultural composition
  • an agricultural composition comprising at least one compound of formula I, Il and/or IV as defined above or an agriculturally acceptable salt thereof and a liquid or solid carrier.
  • Suitable carriers, as well as auxiliaries and further active compounds which may also be contained in the composition of the invention are defined below.
  • the compounds I and Il as well as IV and the compositions according to the invention, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Per- onosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
  • the compounds I, Il and IV and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g.
  • compounds I 1 II and IV and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This in- eludes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • treatment of plant propagation materials with compounds I, Il and IV and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
  • cultiva plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://www.bio.org/speeches/pubs/er/agrLproducts.asp).
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
  • HPPD hydroxyphenylpyruvate dioxygenase
  • ALS acetolactate synthase
  • WO 00/26390 WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imida- zolinones (see e. g.
  • EPSPS enolpyruvylshikimate-3-phosphate synthase
  • GS glutamine synthetase
  • EP-A 242 236, EP-A 242 246) or oxynil herbicides see e. g. US 5,559,024) as a result of conventional methods of breeding or genetic engineering.
  • Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield ® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox.
  • plants are also covered that, by the use of recombinant DNA techniques, are capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as ⁇ -endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bi ) or Cry ⁇ c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp.
  • insecticidal proteins especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as ⁇ -endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), Cry
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Strep- tomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
  • ion channel blockers such as blockers of sodium
  • these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e.
  • insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
  • Genetically modified plants capable to synthesize one or more insecticidal proteins are, e.
  • WO 03/018810 MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CryiAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
  • plants are also covered that, by the use of recombinant DNA techniques, are capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis-related proteins
  • plant disease resistance genes e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum bulbocastanum
  • T4-lysozym e. g. potato cultivars capable of
  • plants are also covered that, by the use of recombinant DNA techniques, are capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • productivity e. g. bio mass production, grain yield, starch content, oil content or protein content
  • plants are also covered that, by the use of recombinant DNA techniques, contain a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health- promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ® rape, DOW Agro Sciences, Canada).
  • a modified amount of substances of content or new substances of content specifically to improve human or animal nutrition, e. g. oil crops that produce health- promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ® rape, DOW Agro Sciences, Canada).
  • plants are also covered that, by the use of recombinant DNA techniques, contain a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora ® potato, BASF SE, Germany).
  • a modified amount of substances of content or new substances of content specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora ® potato, BASF SE, Germany).
  • the compounds I, Il and IV and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
  • Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A. tragopogonis); Altemaria spp. (Alternaria leaf spot) on vegetables, rape ⁇ A. brassicola or brassicae), sugar beets ⁇ A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A.retemata), tomatoes (e. g. A. solanior A.retemata) and wheat; Aphano- myces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A.
  • Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad- leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e.g.
  • Gray leaf spot C. zeae-maydis
  • rice sugar beets (e. g. C. beticola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice
  • Cladosporium spp. on tomatoes e. g. C. fulvum: leaf mold
  • ce- reals e. g. C. herbarum (black ear) on wheat
  • Cochliobolus anamorph: Helminthosporium of Bipolaris
  • spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C.
  • sa- sakii sheath blight
  • Corynespora cassiicola leaf spots
  • Cycloconium spp. e. g. C. oleaginum on olive trees
  • Cylindrocarpon spp. e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.
  • vines e. g. C. liriodendri, teleomorph: Neonectria liriodendr ⁇ .
  • Phellinus punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeo- acremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose) and vines (E. ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (E.
  • betae vegetables (e. g. E. pisi), such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium (teleomorph: Gib- berella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F.
  • vegetables e. g. E. pisi
  • cucurbits e. g. E. cichoracearum
  • cabbages rape (e. g. E. cruciferarum)
  • Eutypa lata Eu
  • Cladosporium vitis on vines; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M.

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Abstract

La présente invention concerne de nouveaux composés de triazole, portant un substituant soufré, et représentés par les formules (I) et (II) telles que décrites ici, des compositions agricoles les contenant, leur utilisation comme fongicides, et des composés intermédiaires mis en œuvre pour leur production.
PCT/EP2010/058541 2009-06-18 2010-06-17 Composés de triazole portant un substituant soufré Ceased WO2010146116A1 (fr)

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WO2018054832A1 (fr) 2016-09-22 2018-03-29 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés triazole
WO2018054829A1 (fr) 2016-09-22 2018-03-29 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés de triazole et leur utilisation en tant que fongicides
WO2018060091A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazolylméthyle à substitution en position 5
WO2018060088A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Dérivés d'imidazolylméthyldioxolane à substitution en position 5 en tant que fongicides
WO2018145921A1 (fr) 2017-02-10 2018-08-16 Bayer Aktiengesellschaft Composition pour lutter contre des micro-organismes nuisibles comprenant des dérivés de 1-(phénoxy-pyridinyl)-2-(1,2,4-triazol-1-yl)-éthanol
WO2018145934A1 (fr) 2017-02-08 2018-08-16 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés de triazole
WO2018145932A1 (fr) 2017-02-08 2018-08-16 Bayer Cropscience Aktiengesellschaft Dérivés de triazole et utilisations de ces derniers en tant que fongicides
WO2018145933A1 (fr) 2017-02-08 2018-08-16 Bayer Aktiengesellschaft Dérivés de triazolethione
EP3421460A1 (fr) 2018-03-15 2019-01-02 Bayer Aktiengesellschaft Fongicides de 2-[(4-alkylphenoxy)-pyridinyl]-1-(1,2,4-triazol-1-yl)alkan-2-ol
WO2020020813A1 (fr) 2018-07-25 2020-01-30 Bayer Aktiengesellschaft Combinaisons de composés actifs fongicides
WO2020020816A1 (fr) 2018-07-26 2020-01-30 Bayer Aktiengesellschaft Nouveaux dérivés de triazole
EP3620053A1 (fr) 2018-12-14 2020-03-11 Bayer Aktiengesellschaft Combinaisons de composés actifs des fongicides

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