WO2013092460A1 - Microbicides bisoximes cycliques - Google Patents

Microbicides bisoximes cycliques Download PDF

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WO2013092460A1
WO2013092460A1 PCT/EP2012/075712 EP2012075712W WO2013092460A1 WO 2013092460 A1 WO2013092460 A1 WO 2013092460A1 EP 2012075712 W EP2012075712 W EP 2012075712W WO 2013092460 A1 WO2013092460 A1 WO 2013092460A1
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alkyl
phenyl
halogen
alkoxy
optionally substituted
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PCT/EP2012/075712
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English (en)
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Daniel Stierli
Kurt Nebel
Martin Pouliot
Laura Quaranta
Stephan Trah
Harald Walter
Werner Zambach
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Syngenta Participations Ag
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Publication of WO2013092460A1 publication Critical patent/WO2013092460A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to novel microbiocidally active, in particular fungicidally active, cyclic bisoxime derivatives. It further relates to intermediates used in the preparation of these compounds, to compositions which comprise these compounds and to their use in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic
  • microorganisms preferably fungi.
  • Fungicidally active bisoximes are described in WO08074418.
  • the present invention accordingly relates to bisoxime derivatives of formula (I)
  • D 1 represents N or C-Y 2 ;
  • D 2 represents N or C-Y 5 ;
  • D 3 represents N or C-Y 7 ;
  • D 1 , D 2 or D 3 is N;
  • A represents hydrogen, halogen, CN, OH, SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl, d-C 8 alkylsulphonyl, NH 2 , Ci-Cio alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, (R 10 O)carbonyl(Ci- C4-alkyl), phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d-C 4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C 3 -C 6 cycloal
  • a and Y 7 together may be -(G 4 ) q -G 5 -G 6 -;
  • X represents X-2, X-3, X-4 or X-5: #— ⁇ — ⁇ —# #— z— z— z— # #— z— z— z— # #— z— z— z— #
  • each R 1 and R 2 independently of one another represent hydrogen, halogen, OH, d-C 4 alkyl,
  • R 1 and R 2 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyi group;
  • each R 3 and R 4 independently of one another represent hydrogen, halogen, C1-C4 alkyl or C1-C4 haloalkyi;
  • each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, Ci- C 4 alkyl, C1-C4 haloalkyi, C 3 -C 6 cycloalkyi, C 3 -C 6 halocycloalkyi, phenyl or CN, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyi, d-C 4 alkoxy and C1-C4 haloalkoxy;
  • R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyi group;
  • groupings X-2, X-3, X-4 and X-5 may contain at most one ring which contains either only one of the radicals Z 1 to Z 14 or two radicals Z 1 to Z 14 or three radicals Z 1 to Z 14 or four radicals Z 1 to Z 14 as ring members; and wherein radicals Z 1 , Z 2 , Z 3 , Z 5 , Z 6 , Z 9 , Z 10 and Z 14 are not substituted by OH;
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and Y 7 independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-C 8 alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, pyridyl, pyrimidinyl, COR 9 , OR 10 , SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl, C r C 8 alkylsulphonyl, N(R n ) 2 , C0 2 R 10 , 0(CO)R 9 , CON(R n ) 2 , NR
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 or Y 6 and Y 7 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R n ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 , or Y 6 and Y 7 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d-C 4 haloal
  • each R 9 independently of one another represents hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyi, C 2 - C 8 alkenyl, C 2 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • each R 10 independently of one another represents hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyi, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups
  • halogen independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and CrC 4 -alkoxy-d-C 4 -alkyl;
  • each R 11 independently of one another represents hydrogen, OH, d-C 8 alkyl, Ci-C 8 alkoxy, Ci-C 8 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, COR 9 or phenyl, wherein the alkyl, alkoxy, alkenyl, alkynyl and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, d-C 4 haloalkyi, C C 4 alkoxy, d-C 4 haloalkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulphinyl and d-C 4 alkylsulphonyl;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • G 1 , G 2 , G 4 and G 5 independently of one another represent -C(R 12 R 13 )-, 0, N(R 14 ) or S;
  • G 3 and G 6 independently of one another represent -C(R 12 R 13 )-, 0, N(R 14 ) or S;
  • each R 12 and R 13 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, Ci- C 4 haloalkyl, Ci-C 4 alkoxy or Ci-C 4 haloalkoxy;
  • R 14 represents hydrogen, OH, Ci-C 4 alkyl, Ci-C 4 alkoxy, C 3 -C 6 cycloalkyl, Ci-C 8 alkylcarbonyl or Ci-C 8 haloalkylcarbonyl;
  • p and q are each independently 0, 1 or 2;
  • Halogen either as a lone substituent or in combination with another substituent (e.g.
  • haloalkyl is generally fluorine, chlorine, bromine or iodine, and usually fluorine, chlorine or bromine.
  • Each alkyl moiety (including the alkyl moiety of alkoxy, alkylthio, etc.) is a straight or branched chain and, depending on the number of carbon atoms it contains, is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, /so-propyl, sec-butyl, /so-butyl, tert-butyl, neo-pentyl, n-heptyl or 1,3-dimethylbutyl, and usually methyl or ethyl.
  • alkenyl and alkynyl groups can be mono- or di-unsaturated and are examples thereof are derived from the above mentioned alkyl groups.
  • Haloalkyl moieties are alkyl moieties which are substituted by one or more of the same or different halogen atoms and are, for example, monofluoromethyl, difluoromethyl,
  • trifluoromethyl monochloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2,2- difluoroethyl, 2-fluoroethyl, 1,1 -difluoroethyl, 1-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1- difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2 -trichloroethyl, and typically trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.
  • Alkoxy is, for example, methoxy, ethoxy, propoxy, / ' so-propoxy, n-butoxy, /so-butoxy, sec- butoxy and tert-butoxy, and usually methoxy or ethoxy.
  • Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2- trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy, and usually difluoromethoxy, 2-chloroethoxy and trifluoromethoxy.
  • Alkylthio is, for example, methylthio, ethylthio, propylthio, /so-propylthio, n-butylthio, iso- butylthio, sec-butylthio or tert- butylthio, and usually methylthio or ethylthio.
  • Alkylsulphonyl is, for example, methylsulphonyl, ethylsulphonyl, propylsulphonyl, iso- propylsulphonyl, n-butylsulphonyl, / ' so-butylsulphonyl, sec-butylsulphonyl or tert-butylsulphonyl, and usually methylsulphonyl or ethylsulphonyl.
  • Alkylsulphinyl is, for example, methylsulphinyl, ethylsulphinyl, propylsulphinyl, iso- propylsulphinyl, n-butylsulphinyl, /so-butylsulphinyl, sec-butylsulphinyl or tert-butylsulphinyl, and usually methylsulphinyl or ethylsulphinyl
  • Cycloalkyl may be saturated or partially unsaturated, preferably fully saturated, and is, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n- propoxymethyl, n-propoxyethyl, /so-propoxymethyl or /so-propoxyethyl.
  • Aryl includes phenyl, naphthyl, anthracyl, fluorenyl and indanyl, but is usually phenyl.
  • Carbocycle includes cycloalkyl groups and aryl groups.
  • Heterocycloalkyl is a non-aromatic ring that may be saturated or partially unsaturated, preferably fully saturated, containing carbon atoms as ring members and at least one heteroatom selected from 0, S and N as ring members.
  • Examples include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, 1,3-dioxolanyl, 1,4-dioxanyl, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, oxazinanyl, morpholinyl, thiomorpholinyl, imidazolidinyl, pyrazolidinyl and piperazinyl, preferably morpholinyl, pyrrolidinyl, piperdinyl and piperazinyl, more preferably morpholinyl and pyrollidinyl.
  • Heteroaryl is, for example, a monovalent monocyclic or bicyclic aromatic hydrocarbon radical.
  • monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, and thiadiazolyl.
  • bicyclic groups include quinolinyl, cinnolinyl, quinoxalinyl, benzimidazolyl, benzothiophenyl, and benzothiadiazolyl.
  • Monocyclic heteroaryl groups are preferred, preferably pyridyl, pyrrolyl, imidazolyl and triazolyl, e.g. 1,2,4 triazolyl, pyridyl and imidazolyl being most preferred.
  • heterocycle and “heterocyclic ring” are used interchangeably and are defined to include heterocycloalkyl and heteroaryl groups. Any reference herein to a heterocycle or heterocyclic ring preferably refers to the specific examples given under the definition of heteroaryl and heterocycloalkyl above, and are preferably morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl pyridyl, pyrrolyl, imidazolyl and triazolyl, e.g. 1,2,4 triazolyl, more preferably morpholinyl, pyrollidinyl, pyridyl and imidazolyl.
  • a moiety is indicated as being (optionally) substituted, e.g. alkyl, this includes those moieties where they are part of a larger group, e.g. the alkyl in the alkylthio group.
  • a moiety is indicated as being optionally substituted by one or more other groups, preferably there are one to five optional substituents, more preferably one to three optional substituents.
  • D 1 represents N or C-Y 2 ;
  • D 2 represents N or C-Y 5 ;
  • D 3 represents N or C-Y 7 ;
  • D 1 , D 2 or D 3 is N;
  • D 1 represents C-Y 2
  • D 2 represents N
  • D 3 represents C-Y 7 .
  • D 1 represents C-Y 2
  • D 2 represents C-Y 5
  • D 3 represents N.
  • D 1 represents N
  • D 2 represents C-Y 5
  • D 3 represents C-Y 7 .
  • D 1 represents N
  • D 2 represents N
  • D 3 represents C-Y 7 .
  • D 1 represents N
  • D 2 represents C-Y 5
  • D 3 represents N
  • A represents hydrogen, halogen, CN, OH, SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl, d-C 8 alkylsulphonyl, NH 2 , Ci-Cio alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, (R 10 O)carbonyl(Ci- C 4 -alkyl), phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d-C 4 haloalkyl, Ci-C 4 alkoxy
  • a and Y 7 together may be -(G 4 ) q -G 5 -G 6 -.
  • A represents hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyi, phenyl or pyridyl, wherein the alkyl, cycloalkyi, phenyl and pyridyl are optionally substituted by one or more groups, e.g.
  • one to five groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyi, OH, C1-C4 alkoxy, C1-C4 haloalkoxy and C 3 -C 6 cycloalkyi.
  • A represents hydrogen, C1-C4 alkyl, phenyl or pyridyl, wherein alkyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, OH, C1-C4 alkoxy and d-C 4 haloalkoxy, and wherein phenyl and pyridyl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyi, OH, d-C 4 alkoxy, CrC 4 haloalkoxy and C 3 -C 6 cycloalkyi.
  • A represents hydrogen, C1-C4 alkyl, phenyl or pyridin-2-yl, wherein the phenyl and pyridin-2-yl are optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, methyl, halomethyl, methoxy and
  • A represents C1-C4 alkyl.
  • compounds A represents pyridyl, optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C4-alkyl, C1-C4- haloalkyl, d-C 4 -alkoxy, d-C 4 -haloalkoxy, C 3 -C 6 cycloalkyi and a 5 or 6-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms.
  • the heterocycle is preferably one as defined herein, preferably morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g. 1,2,4 triazolyl, more preferably morpholinyl, pyrollidinyl, pyridyl or imidazolyl.
  • this preferred group of compounds A preferably represents pyridin-2-yl, optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d- C 4 alkyl, C1-C4 haloalkyi, C1-C4 alkoxy, C1-C4 haloalkoxy, C 3 -C 6 cycloalkyi and a 5 or 6-membered heterocycle containing one to three heteroatoms independently selected from 0, S and N, providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms.
  • the heterocycle is preferably one as defined herein, preferably morpholinyl, pyrrolidinyl, piperdinyl, piperazinyl, pyridyl, pyrrolyl, imidazolyl or triazolyl, e.g. 1,2,4 triazolyl, more preferably morpholinyl, pyrollidinyl, pyridyl or imidazolyl.
  • A represents hydrogen, C1-C4 alkyl, C 2 -C 4 alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from d-C 4 alkyi, Ci-C 4 haloalkyi, halogen, CN, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • A represents hydrogen, halogen, CN, OH, SH, Ci-Cs alkylthio, Ci-C 8 alkylsulphinyl, Ci-C 8 alkylsulphonyl, NH 2 , C1-C10 alkyi, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, (d-C 4 alkyloxycarbonyl) Ci-C 4 alkyi, (Ci-C 4 alkyl)0 2 C, phenyl or pyridyl, wherein the alkyi, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyi, Ci-C 4 haloalkyi, Ci-C 4 alkoxy, d-
  • A represents hydrogen, (Ci-C 4 alkyl)0 2 C, C1-C10 alkyi, phenyl or pyridyl, wherein the alkyi, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyi, Ci-C 4 haloalkyi, C 3 -C 6 cycloalkyl and a 5- or 6-membered heterocycle containing one to three nitrogen atoms.
  • X represents X-2, X-3, X-4 or X-5:
  • X represents X-3 or X-5. More preferably X represents X-3.
  • Z 1 , Z 2 , Z 3 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 13 and Z 14 independently of one another represent methylene, halomethylene, CH(CH 3 ) or C(CH 3 ) 2 .
  • Z 1 , Z 2 , Z 3 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 13 and Z 14 represent methylene or halomethylene.
  • Z 1 , Z 2 , Z 3 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 13 and Z 14 represent methylene.
  • Each R 1 and R 2 independently of one another represent hydrogen, halogen, OH, Ci-C 4 alkyl, C1-C4 haloalkyi, C 3 -C 6 cycloalkyi, C 3 -C 6 halocycloalkyi, C1-C4 alkylthio, C1-C4 alkylsulphinyl, C1-C4 alkylsulphonyl, phenyl or CN, wherein the phenyl is optionally substituted by one or more groups, e.g.
  • R 1 and R 2 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyi group.
  • Each R 3 and R 4 independently of one another represent hydrogen, halogen, C1-C4 alkyl or C1-C4 haloalkyi.
  • each R 3 and R 4 independently of one another represent hydrogen, halogen, methyl or halomethyl.
  • Each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, Ci- C 4 alkyl, C1-C4 haloalkyi, C 3 -C 6 cycloalkyi, C 3 -C 6 halocycloalkyi, phenyl or CN, wherein phenyl is optionally substituted by one or more groups, e.g.
  • R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyi group.
  • each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, C1-C4 alkyl, C1-C4 haloalkyi, C 3 -C 6 cycloalkyi, phenyl or CN, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, C1-C4 haloalkyi, d-C 4 alkoxy and d-C 4 haloalkoxy; or R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyi group.
  • each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, d-C 4 alkyl, d-C 4 haloalkyi, phenyl or CN wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; or R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group optionally substituted by halogen.
  • each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, d-C 4 alkyl, C1-C4 haloalkyi or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; or R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group optionally substituted by halogen.
  • Y 1 , Y 2 , ⁇ 3 , ⁇ 4 , ⁇ 5 , Y 6 and ⁇ 7 independently of one another represent hydrogen, halogen, CN, N0 2 , Ci-C 8 alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, phenyl, pyridyl, pyrimidinyl, COR 9 , OR 10 , SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl, d-C 8 alkylsulphonyl, N(R n ) 2 , C0 2 R 10 , 0(CO)R 9 , CON(R n ) 2 , NR
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 or Y 6 and Y 7 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R n ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms, or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 or Y 6 and Y 7 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d-C 4 haloalkyi
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and Y 7 independently of one represent hydrogen, halogen, OH, CN, Ci-C 8 alkyl, Ci-C 8 haloalkyi, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, Ci-C 8 alkylthio, C 3 -C 8 cycloalkyi, phenyl, pyridyl, N(R n ) 2 , or NR n COR 9 , wherein phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy and d-C 4 haloalkoxy;
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 or Y 6 and Y 7 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R n ) 2 and wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 or Y 6 and Y 7 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • each R 9 independently represents d-C 8 alkyl or Ci-C 8 haloalkyi
  • each R 11 independently of one another represents hydrogen, Ci-C 8 alkyl, COR 9 or phenyl, wherein the phenyl is optionally substituted by one or more group independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, d-C 4 haloalkyi, d-C 4 alkoxy, d-C 4 haloalkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulphinyl and d-C 4 alkylsulphonyl; wherein when two radicals R are attached to the same nitrogen atom, these radicals can be identical or different;
  • cycle formed is optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl.
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and Y 7 independently of one another represent hydrogen, CN, OH, halogen, d-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy, d-C 4 haloalkoxy, C 3 -C 6 cycloalkyl, Ci-C 4 alkylthio, N(R n ) 2 , NR n COR 9 or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, d-C 4 alkyl, Ci-C 4 haloalkyi, d- C 4 alkoxy and d-C 4 haloalkoxy;
  • each R 9 independently represents d-C 4 alkyl or Ci-C 4 haloalkyi
  • each R 11 independently of one another represents hydrogen, Ci-Cs alkyl or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, d-C 4 haloalkyi, d-C 4 alkoxy and d-C 4 haloalkoxy; wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and Y 7 independently of one another represent hydrogen, CN, OH, halogen, d-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy, d-C 4 haloalkoxy, C 3 -C 6 cycloalkyl, d-C 4 alkylthio, N(R n ) 2 , NR n COR 9 or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected selected from halogen, methyl, CN, methoxy, halomethyl and halomethoxy;
  • each R 9 independently represents d-C 4 alkyl or Ci-C 4 haloalkyi; wherein each R independently of one another represents hydrogen, Ci-C 8 alkyl or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and Y 7 independently of one another represent hydrogen, CN, OH, halogen, d-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy, d-C 4 haloalkoxy, C 3 -C 6 cycloalkyi, d-C 4 alkylthio, N(R n ) 2 , NR n COR 9 or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected selected from halogen, methyl, CN, methoxy, halomethyl and halomethoxy;
  • each R 9 independently represents d-C 4 alkyl or Ci-C 4 haloalkyi
  • each R 11 independently of one another represents hydrogen, Ci-C 8 alkyl or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • Each R 9 independently of one another represents hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyi, C 2 - C 8 alkenyl, C 2 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups, e.g.
  • one to five groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d-C 4 haloalkyi, Ci- C 4 alkoxy and Ci-C 4 haloalkoxy.
  • each R 9 independently of one another represent Ci-Cs alkyl or d-C 8 haloalkyi.
  • each R 9 independently of one another represent d-C 4 alkyl or Ci-C 4 haloalkyi.
  • Each R 10 independently of one another represents hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyi, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups, e.g.
  • one to five groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, Ci-C 4 haloalkyi, d-C 4 alkoxy, Ci-C 4 -haloalkoxy and Ci-C 4 -alkoxy-Ci-C 4 -alkyl.
  • Each R 11 independently of one another represents hydrogen, OH, Ci-C 8 alkyl, Ci-C 8 alkoxy, Ci-C 8 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, COR 9 or phenyl, wherein the alkyl, alkoxy, alkenyl, alkynyl and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, d-C 4 haloalkyi, d-C 4 alkoxy, d-C 4 haloalkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulphinyl and d-C 4 alkylsulphonyl;
  • radicals R 11 when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different; wherein when two radicals R are attached to the same nitrogen atom, both of these radicals cannot be OH, d-C 4 alkoxy or Ci-C 4 haloalkoxy;
  • each R 11 independently of one another represents hydrogen, d-C 8 alkyl, COR 9 or phenyl, wherein the phenyl is optionally substituted by one or more group independently selected from halogen, CN, NH 2 , N0 2 , OH, d-C 4 alkyl, d-C 4 haloalkyi, C C 4 alkoxy, d-C 4 haloalkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulphinyl and d-C 4 alkylsulphonyl;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • cycle formed is optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl.
  • each R 11 independently of one another represents hydrogen, d-C 8 alkyl or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy; wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different; wherein when two radicals R are attached to the same nitrogen atom, both of these radicals cannot be OH, d-C 4 alkoxy or Ci-C 4 haloalkoxy.
  • each R 11 independently of one another represents hydrogen, Ci-Cs alkyl or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyi, d-C 4 alkoxy and Ci-C 4 haloalkoxy.
  • G 1 , G 2 , G 4 and G 5 independently of one another represent -C(R 12 R 13 )- , 0, N(R 14 ) or S;
  • G 3 and G 6 independently of one another represent -C(R 12 R 13 )-, 0, N(R 14 ) or S;
  • G 1 , G 2 , G 4 and G 5 independently of one another represent -C(R 12 R 13 )- ;
  • G 3 and G 6 independently of one another represent -C(R 12 R 13 )-, 0, N(R 14 ) or S;
  • G 1 , G 2 , G 4 and G 5 independently of one another represent -C(R 12 R 13 )-;
  • G 3 and G 6 independently of one another represent -C(R 12 R 13 )-, 0, N(R 14 ) or S.
  • G 1 , G 2 , G 3 , G 4 , G 5 and G 6 independently of one another represent - C(R 12 R 13 )-.
  • G 1 , G 2 , G 3 , G 4 , G 5 and G 6 represent methylene.
  • Each R 12 and R 13 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyi, d-C 4 alkoxy or Ci-C 4 haloalkoxy.
  • R 14 represents hydrogen, OH, d-C 4 alkyl, Ci-C 4 alkoxy, d-C 6 -cycloalkyl, Ci-Cs alkylcarbonyl or Ci-Q haloalkylcarbonyl.
  • p and q are each independently of one another 0, 1 or 2.
  • p and q are each independently of one another 1 or 2.
  • D 1 represents N or C-Y 2 ;
  • D 2 represents N or C-Y 5 ;
  • D 3 represents N or C-Y 7 ;
  • D 1 , D 2 or D 3 is N;
  • A represents hydrogen, halogen, CN, OH, SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl, d-C 8 alkylsulphonyl, NH 2 , Ci-Cio alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, (R 10 O)carbonyl(Ci- C4-alkyl), phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci- haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C 3
  • a and Y 7 together may be -(G 4 ) q -G 5 -G 6 -.
  • X represents X-2, X-3, X-4 or X-5:
  • each R 1 and R 2 independently of one another represent hydrogen, halogen, OH, Ci-d alkyl,
  • C1-C4 haloalkyl C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, Ci-C 4 alkylthio, C1-C4 alkylsulphinyl, Ci-C 4 alkylsulphonyl, phenyl or CN, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, Ci-d alkoxy and C1-C4 haloalkoxy;
  • R 1 and R 2 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group;
  • each R 3 and R 4 independently of one another represent hydrogen, halogen, d-C 4 alkyl or C1-C4 haloalkyl;
  • each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, Ci- C 4 alkyl, Ci-d haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, phenyl or CN, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, d-d alkyl, Ci- haloalkyl, Ci-d alkoxy and Ci-d haloalkoxy;
  • R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group; wherein the groupings X-2, X-3, X-4 and X-5 may contain at most one ring which contains either only one of the radicals Z 1 to Z 14 or two radicals Z 1 to Z 14 or three radicals Z 1 to Z 14 or four radicals Z 1 to Z 14 as ring members; and wherein radicals Z 1 , Z 2 , Z 3 , Z 5 , Z 6 , Z 9 , Z 10 and Z 14 are not substituted by OH;
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and Y 7 independently of one another represent hydrogen, halogen, CN,
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 or Y 6 and Y 7 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from 0, S, N and N(R n ), providing that the heterocycle does not contain adjacent oxygen atoms, adjacent sulphur atoms or adjacent sulphur and oxygen atoms, and wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 or Y 6 and Y 7 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, C C 4 alkyl, C r C 4 haloalkyi, C
  • each R 9 independently of one another represents hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyi, C 2 - C 8 alkenyl, C 2 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • each R 10 independently of one another represents hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyi, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, benzyl, phenyl or pyridyl, wherein the alkyl, cycloalkyi, alkenyl, alkynyl, phenyl, benzyl and pyridyl are optionally substituted by one or more groups
  • halogen independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 -haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy and d-C 4 -alkoxy-Ci-C 4 -alkyl;
  • each R 11 independently of one another represents hydrogen, OH, Ci-C 8 alkyl, Ci-C 8 alkoxy, Ci-C 8 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, COR 9 or phenyl, wherein the alkyl, alkoxy, alkenyl, alkynyl and phenyl are optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi, C C 4 alkoxy, C C 4 haloalkoxy, Ci-C 4 alkylthio, Ci-C 4 alkylsulphinyl and d-C 4 alkylsulphonyl;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • cycle formed is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • G 1 , G 2 , G 4 and G 5 independently of one another represent -C(R 12 R 13 )-;
  • G 3 and G 6 independently of one another represent -C(R 12 R 13 )-, 0, N(R 14 ) or S;
  • each R 12 and R 13 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, Ci- C 4 haloalkyi, Ci-C 4 alkoxy or Ci-C 4 haloalkoxy;
  • R 14 represents hydrogen, OH, d-C 4 alkyl, Ci-C 4 alkoxy, C 3 -C 6 cycloalkyi, Ci-C 8 alkylcarbonyl or Ci-C 8 haloalkylcarbonyl;
  • p and q are each independently 0, 1 or 2.
  • A represents hydrogen, Ci-C 8 alkyl, C 3 -C 8 cycloalkyi, phenyl or pyridyl, wherein the alkyl, cycloalkyi, phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyi, OH, d-C 4 alkoxy, Ci-C 4 haloalkoxy and C 3 -C 6 cycloalkyi;
  • X represents X-3
  • Z 3 and Z 5 independently of one another represent methylene or halomethylene
  • each R 3 and R 4 independently of one another represent hydrogen, halogen, methyl or halomethyl
  • each R 5 , R 6 , R 7 and R 8 independently of one another represent hydrogen, halogen, OH, Ci- C 4 alkyl, Ci-C 4 haloalkyi, phenyl or CN, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy or halomethoxy;
  • R 5 and R 6 together with the carbon atom to which they are attached may form a C3-C6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group;
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and Y 7 independently of one represent hydrogen, halogen, OH, CN, d-
  • Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 or Y 6 and Y 7 together with the fragment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R n ) 2 and wherein the ring formed by Y 1 and Y 2 , Y 2 and Y 3 , Y 4 and Y 5 , Y 5 and Y 6 or Y 6 and Y 7 is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, C1-C4 alkyl, C1-C4 haloalkyi, C1-C4 alkoxy and C1-C4 haloalkoxy;
  • each R 9 independently represents Ci-C 8 alkyl or Ci-C 8 haloalkyi
  • each R 11 independently of one another represents hydrogen, Ci-C 8 alkyl, COR 9 or phenyl, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, C1-C4 alkyl, C1-C4 haloalkyi, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulphinyl and C1-C4 alkylsulphonyl;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • cycle formed is optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl;
  • G 1 , G 2 , G 3 , G 4 , G 5 and G 6 independently of one another represent -C(R 12 R 13 )-;
  • A represents hydrogen, Ci-C 4 alkyl, phenyl or pyridyl, wherein alkyl is optionally substituted by one or more groups independently selected from halogen, OH, C1-C4 alkoxy and C1-C4 haloalkoxy, and wherein phenyl and pyridyl are optionally substituted by one or more groups independently selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, OH, d-C 4 alkoxy, Ci-C 4 haloalkoxy and C 3 -C 6 cycloalkyi;
  • X represents X-3
  • Z 3 and Z 5 represent methylene
  • each R 3 and R 4 independently of one another represent hydrogen, halogen, methyl or halomethyl
  • each R 5 and R 6 independently of one another represent hydrogen, halogen, OH, d-C 4 alkyl, Ci-C 4 haloalkyl, phenyl or CN, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy or halomethoxy; or R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyl group;
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and Y 7 independently of one another represent hydrogen, CN, OH, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, Ci-C 4 alkylthio, C 3 -C 6 cycloalkyi, N(R n ) 2 , NR n COR 9 or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • each R 9 independently represents d-C 4 alkyl or Ci-C 4 haloalkyl
  • each R 11 independently of one another represents hydrogen, Ci-C 8 alkyl or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, Ci-C 4 alkyl, d-C 4 haloalkyl, C C 4 alkoxy and C r C 4 haloalkoxy;
  • radicals R 11 wherein when two radicals R 11 are attached to the same nitrogen atom, these radicals can be identical or different;
  • G 1 , G 2 , G 3 , G 4 , G 5 and G 6 represent methylene; p and q are each independently 0, 1 or 2.
  • A represents hydrogen, d-C 4 alkyl, phenyl or pyridin-2-yl wherein phenyl and pyridin-2-yl are optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy;
  • X represents X-3
  • Z 3 and Z 5 represent methylene
  • each R 3 and R 4 independently of one another represent hydrogen, halogen, methyl or halomethyl
  • each R 5 and R 6 independently of one another represent hydrogen, halogen, OH, d-C 4 alkyl,
  • Ci-C 4 haloalkyl, phenyl or CN wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy or halomethoxy; or R 5 and R 6 together with the carbon atom to which they are attached may form a C 3 -C 6 cycloalkyi group or a C 3 -C 6 halocycloalkyl group;
  • Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and Y 7 independently of one another represent hydrogen, CN, OH, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, d-C 4 alkylthio, C 3 -C 6 cycloalkyi, N(R n ) 2 , NR n COR 9 or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected selected from halogen, methyl, CN, methoxy, halomethyl and halomethoxy;
  • each R 9 independently represents d-C 4 alkyl or Ci-C 4 haloalkyl
  • each R 11 independently of one another represents hydrogen, d-C 8 alkyl or phenyl, wherein phenyl is optionally substituted by one or more groups independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy and Ci-C 4 haloalkoxy;
  • G 1 , G 2 , G 3 , G 4 , G 5 and G 6 represent methylene
  • p and q are each independently 0, 1 or 2.
  • p is 1 and -G ⁇ G ⁇ G 3 - represent -CH 2 -CH 2 -CH 2 -.
  • a and Y 7 together represent -CH 2 -CH 2 -CH 2 -.
  • the invention provides a compound of formula (II) FT -X
  • R represents -ONH 2 , halogen, -0-S0 2 -R 2B or one of the groups LG, C-l, C-2A or C-2B:
  • R 28 represents C1-C4 alkyl, C1-C4 haloalkyi or phenyl, wherein the phenyl is optionally substituted by one or two substituents independently selected from methyl, trihalomethyl, N0 2 , CN, C1-C7 alkoxycarbonyl;
  • X" represents halogen
  • R 37 represents either A as defined herein for compounds of formula (I) or the group R '
  • R 27 represents -ONH 2 , -0-S0 2 -R 28 or one of the groups LG, C-l or C-2.
  • R 27 represents -ONH 2 , tosylate, mesylate, triflate or one of the groups LG, C-l or C-2.
  • X' represents one of the groupings X'-l, X'-2 or X'-3:
  • R 29 and R 30 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyi, phenyl or CN, wherein phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkyoxy; and
  • G 1 , G 2 , G 3 , D 1 , Y 1 , Y 3 and p are as defined for a compound of formula (I);
  • R 29 and R 30 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyi, phenyl or CN, wherein the phenyl is optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and
  • At least one of Y 4 , Y 5 or Y 6 represents pyrimidinyl, Ci-Cs haloalkylthio, Ci-Cs haloalkylsulphinyl or Ci-Cs haloalkylsulphonyl ,wherein the pyrimidinyl is optionally substituted by one or more groups independently selected from halogen, CN, NH 2 , N0 2 , OH, C C 4 alkyl, C C 4 haloalkyi, C C 4 alkoxy, d-C 4 haloalkoxy, d-C 4 alkylthio, Ci-C 4 alkylsulphinyl and Ci-C 4 alkylsulphonyl.
  • G 3 represents N(R 14 ) wherein R 14 represents
  • X' represents X'-l.
  • G 1 , G 2 , G 3 , p, D 1 , Y 1 and Y 3 are as defined for a compound of formula I, or a salt or N-oxide thereof.
  • the preferred definitions of G 1 , G 2 , G 3 , p, D 1 , Y 1 and Y 3 are as defined in respect of compounds of formula (I) above also apply to compounds of formula (IVa).
  • Y 6 is Ci-C 6 alkyl, halogen, NH 2 , CrC 6 haloalkyl, Ci-Cs haloalkoxy, or Ci-C 6 haloalkoxy;
  • Y 7 and Y 8 independently of one another represent hydrogen, halogen, CN, N0 2 , CrC 8 alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, C 3 -C 8 cycloalkyi, C 2 -C 8 alkenyl, C 2 - C 8 alkynyl, phenyl, pyridyl, COR 13 , OR 22 , SH, Ci-C 8 alkylthio, Ci-C 8 alkylsulphinyl, Ci-C 8 alkylsulphonyl, N(R 23 ) 2 , C0 2 R 22 , 0(CO)R 13 , CON(R 23 ) 2 , NR 23 COR 13 or CR 13 N-OR 22 , wherein the alkyl, alkoxy, cycloalkyi, alkenyl,
  • G 1 and G 2 independently represent -C(R 24 )(R 25 )-;
  • G 3 represents -C(R 24 )(R 25 )-, O, N(R 26 ) or S;
  • each R 24 and R 25 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, Ci- C 4 haloalkyl, Ci-C 4 alkoxy, or d-C 4 haloalkyl;
  • R 26 is hydrogen, OH, d-C 4 alkyl or Ci-C 4 alkoxy; p is 0, 1 or 2. Preferably, p is 1 or 2.
  • Y 6 is hydrogen, methyl or halomethyl.
  • Y 6 is methyl or halomethyl.
  • the invention provides a compound of formula XVI.
  • G 1 , G 2 , G 3 , p, D 1 , Y 1 and Y 3 are as defined herein for a compound of formula I, and wherein R 38 is hydrogen, CO-CH 3 , CO-CH 2 CH 3 , CO-CH 2 CH 2 CH 3 , CO-CH(CH 3 ) 2 , CO-CF 3 , CO- CF 2 CF 3 , -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , -CH(CH 3 ) 2 , or a salt or N-oxide thereof.
  • the invention provides a process for the production of a compound of formula (I) comprising reacting a compound of formula (lib) with a compound of formula (X) as shown in scheme X
  • R represents Ci-C 4 alkyl, d-C 4 haloalkyl or phenyl, wherein the phenyl is optionally substituted by one or two substituents independently selected from methyl, trihalomethyl, N0 2 , CN, C1-C7 alkoxycarbonyl; and
  • the compounds of formula (I) may exist as different geometric or optical isomers or in different tautomeric forms. These may be separated and isolated by well-known (usually chromatographic) techniques, and all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms, such as deuterated compounds, are part of the present invention.
  • the carbon-nitrogen double bonds of the compound of formula (I) allow the four cis/trans isomers shown below:
  • the present invention includes each of these isomers.
  • the invention may provide a compound of formula (I) as just one of these isomers or as a mixture of one or more isomers in any ratio.
  • the invention also includes the corresponding isomers of the intermediates described herein, e.g. compounds (II), (III) and (VIII).
  • a reaction scheme depicts synthesis of one geometric isomer
  • the scheme also includes synthesis of the other geometric isomers where possible.
  • Scheme X shown above encompasses the reactions:
  • Table X represents Table 1 (when X is 1), Table 2 (when X is 2), Table 3 (when X is 3), Table 4 (when X is 4), Table 5 (when X is 5), Table 6 (when X is 6), Table 7 (when X is 7).
  • Y 1 , Y 3 , Y 4 , Y 6 and X have the specific meanings given in the table.
  • Table 7 This table discloses com ounds 1.01 to 1.192 of the formula (I-VII)
  • Y 1 , Y 3 , Y 4 , Y 6 and X have the specific meanings given in the table.
  • the compounds in Tables 1 to 7 include all isomers, tautomers and mixtures thereof, including the cis/trans isomers shown above.
  • the compounds of the invention may be made by a variety of methods, illustrated in schemes 1-8.
  • the compounds depicted in the schemes also indicate any isomers and tautomers, in particular the geometric isomers arising from the oxime and oxime ether moieties.
  • Compounds of formula (I) may be prepared by reacting a compound of formula (Ha), that is a compound of formula (II) wherein R is -ONH 2 , with a compound of formula (VI), wherein A, D 2 , D 3 , Y 4 and Y 6 are as defined herein for compounds of formula (I), and T 1 and T 2 are Ci-C 8 alkoxy, or T 1 and T 2 together with the carbon they are attached to form a carbonyl group or an acetal or ketal function of the form C(0-Ci-C 6 -alkylidene-0) whereby the alkylidene fragment may optionally be mono- to tetra-substituted by d-C 6 alkyl, as seen in scheme 1.
  • Hydroxylamine derivatives of formula (Ila) may be made by reacting compounds of formula (IV), wherein G 1 , G 2 , G 3 , p, D 1 , Y 1 and Y 3 are as defined herein for compounds of formula (I), and T 1 and T 2 are Ci-Cs alkoxy, or T 1 and T 2 together with the carbon they are attached to form a carbonyl group or an acetal or ketal function of the form C(0-Ci-C 6 - alkylidene-O) whereby the alkylidene fragment may optionally be mono- to tetra -substituted by Ci-C 6 alkyl, with a bishydroxylamine derivative of formula (V), wherein X is as defined herein for a compound of formula (I) and R 31 and R 32 are either hydrogen or suitable protecting groups such as tert-butyloxycarbonyl (BOC), allyloxycarbonyl, fluorenylmethyloxycarbonyl (FMOC), formyl,
  • R 31 and R 32 are hydrogen, in order to optimize the yield of compound (Ila) an excess of intermediate (V) over intermediate (IV) may preferably be used. If R 31 or R 32 is not hydrogen, the hydroxylamine derivative may be deprotected using techniques well known to the person skilled in the art. Examples can be found in Greene, T. W., Wuts, P. G. N., Protective Groups in Organic Synthesis, John Wiley & Sons, Inc, 2006.
  • compounds of formula (I) may be prepared by reacting a compound of formula (IV) and a compound of formula (VI) in the presence of a compound of formula (VII), wherein X is as defined herein for compounds of formula (I).
  • Compounds of formula (IV) and (VI) are described under Scheme 1.
  • compounds of formula (I) can be obtained by reacting a compound of formula (lib), that is a compound of formula (II) wherein R 27 is a halogen, in particular chlorine, bromine or iodine, or a sulfonic acid ester group, such as mesylate, tosylate, triflate, a phenylsulfonic acid ester, a nitro-phenylsulfonic acid ester, a nonafluorobutylsulfonic acid ester or LG with a compound of formula (X), wherein A, D 2 , D 3 , Y 4 and Y 6 are as defined herein for compounds of formula (I) (scheme 3).
  • a compound of formula (lib) that is a compound of formula (II) wherein R 27 is a halogen, in particular chlorine, bromine or iodine, or a sulfonic acid ester group, such as mesylate, tosylate, triflate, a
  • Compounds of formula (lib) may be obtained by reacting an oxime of formula (VIII) with a compound of formula (IX), wherein R 27 is as defined herein for compounds of formula (lib) and R 33 is a halogen, in particular chlorine, bromine or iodine, a sulfonic acid ester group, or the group LG (scheme 3).
  • R 27 and R 33 may be the same or different.
  • R 33 is a better leaving group under the conditions of the reaction, such as tosylate or bromine when R is chlorine.
  • an excess of the compound of formula (IX) relative to the oxime (VIII) would be used in the reaction, especially when R 27 and R 33 are the same.
  • Oximes of formula (VIII) may be obtained by a condensation reaction, whereby a compound of formula (IV), wherein G 1 , G 2 , G 3 , p, D 1 , Y 1 and Y 3 are as defined herein for compounds of formula (I) and T 1 and T 2 are Ci-C 8 alkoxy, or T 1 and T 2 together with the carbon they are attached to form a carbonyl group or an acetal or ketal function of the form C(0-Ci-C 6 - alkylidene-O) whereby the alkylidene fragment may optionally be mono- to tetra -substituted by Ci-C 6 -alkyl, is reacted with hydroxylamine, or, alternatively, with a salt of hydroxylamine.
  • condensation processes is given below.
  • oximes of formula (VIII) can be obtained by a nitrosation reaction of compounds of formula (XI), wherein G 1 , G 2 , G 3 , p, D 1 , Y 1 and Y 3 are as defined herein for compounds of formula (I), with base and an alkyl nitrite, as seen in scheme 5.
  • Typical bases include lithium diisopropyl amide (LDA), lithium hexamethyldisilazane, n-butyl lithium, s-butyl lithium, tert-butyl lithium, sodium tert-butylate or potassium tert-butylate .
  • Typical alkyl nitrites include isopentyl nitrite and tert-butyl nitrite.
  • the compound of formula (XI), the alkyl nitrite or the base can be used in different stoichiometric amounts, with each reagent possibly being in excess with respect to the others.
  • such reactions are carried out under nonaqueous conditions in an inert solvent such as hexane, heptanes, cyclohexane, toluene or ethers such as THF or tert-butyl methyl ether.
  • the reaction may be performed at temperatures ranging from -80 to 250°C, preferably between -50 and 120°C.
  • Such reactions can lead to a mixture of the E- and the Z-oxime (ether) product, or the product may also be exclusively either the E- or the Z-oxime (ether).
  • the compounds of (lib) can be formed by reacting a hydroxylamine derivative of formula (XIII), wherein R 27 halogen, with a compound of formula (IV), as seen in scheme 6.
  • Compounds of formula (XIII) can be made by alkylating a hydroxylamine derivative of formula (XII), wherein R 34 and R 35 , either independently of each other, or together with each other and the nitrogen atom to which they are attached, are protecting groups, such as tert- butoxy carbonyl, acetyl, benzyl, or phthalyl, with the alkylating agent (IX), wherein R is halogen and R 33 is halogen, in particular chloro, bromo or iodo, a sulfonic acid ester group, or LG (scheme 6). Typical conditions for such an alkylation reaction may be found below.
  • the protecting groups or group can then be removed using techniques well known to a person skilled in the art, examples of which can be found in Greene, T. W., Wuts, P. G. N., Protective Groups in Organic Synthesis, John Wiley & Sons, Inc, 2006.
  • Z 4 , Z 8 and Z 13 represent C(OH)R 30 and Z 5
  • Z 9 and Z 14 represent CHR 29 wherein R 29 and R 30 independently of one another represent hydrogen, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, phenyl or CN, wherein phenyl is optionally substituted by one or more groups, e.g. one to five groups, independently selected from halogen, CN, Ci-C 4 alkyl, Ci-C 4 haloalkyi, Ci-C 4 alkoxy and Ci-C 4 haloalkyoxy, can be made by reacting compounds of formula (III) with compounds of formula (X) (scheme 7).
  • Compounds of formula (I) may be formed from compounds of formula (lid), that is a compound of formula (II) wherein R 27 represents C-2B, as seen in scheme 8. This can be done by displacing the group X" with a suitable derivative of the group A or the fragment R 37 using one of several techniques well known to the person skilled in the art, including coupling reactions such as Suzuki (Suzuki-Miyaura) couplings and Stille couplings.
  • the Suzuki coupling comprises the reaction between an organoboron compound, such as the boronic acid derivative of A or R 37 or their esters and a halide of formula (lid) to give compounds of formula (I).
  • organoboron compound such as the boronic acid derivative of A or R 37 or their esters
  • a halide of formula (lid) to give compounds of formula (I).
  • the reaction may be done in the presence of a palladium catalyst such as Pd(PPh 3 ) 4 , Pd(OAc) 2 , Pd(dppf)CI 2 and a base such as Na 2 C0 3 , Ba(OH) 2 , K 3 P0 4 , Cs 2 C0 3 , K 2 C0 3 , KF, NaOH or alkali alcoholates, such as potassium tert-butoxide or sodium ethoxide.
  • Typical catalyst loadings are in the range of 0.01 to 10 mol%.
  • Preferred solvents for such cross coupling reactions include ethers such as THF or dimethoxyethane, acetonitrile, DMF, NMP, benzene or toluene or a mixture of such solvents. Such solvents can also be used together with water.
  • the preferred temperature range for carrying out such reactions is between 0°C and 180°C.
  • the Stille coupling comprises the use of an organotin compound, such as the tributylstannane derivative of A or R 37 and a halide of formula (lid) to give compounds of formula (I).
  • the reaction can be done in the presence of a palladium catalyst such as Pd(PPh 3 ) 4 , Pd 2 (dba) 3 .CHCI 3 with or with an added ligand such as P(2-furyl) 3 or Pd(OAc) 2 , Pd(dppf)CI 2 ,
  • a palladium catalyst such as Pd(PPh 3 ) 4 , Pd 2 (dba) 3 .CHCI 3 with or with an added ligand such as P(2-furyl) 3 or Pd(OAc) 2 , Pd(dppf)CI 2 ,
  • Pd(MeCN) 2 CI 2 Typical catalyst loadings are in the range of 0.01 to 10 mol%.
  • Preferred solvents for such cross coupling reactions include ethers such as THF or dimethoxyethane, acetonitrile, DMF, NMP, benzene or toluene. Such solvents can also be used together with water.
  • the preferred temperature range for carrying out such reactions is between 0°C and 180°C.
  • Compounds of formula (lid) can be formed from compounds of formula (lie), that is a compound of formula (II) wherein R 27 represents C-l, by the action of a halogenating agent.
  • the reaction can be performed using an excess of either the halogenating agent, equimolar amounts of halogenating agent and the hydroxamic acid ester (XV), or with an excess of the hydroxamic acid ester (lie). Preferentially it is carried out with an excess of halogenating agent over the hydroxamic acid ester (lie).
  • Typical halogenating agents include CCI 4 or CBr 4 along with and a phosphine such as triphenyl phosphine or tributylphosphine.
  • Other typical halogenating agents include Et 2 NSF 3 , (MeOCH 2 CH 2 ) 2 NSF 3 (Deoxo-Fluor), morpholinotrifluorosulfurane and SF 4 , SOCI 2 , COCI 2 , PCI 5 , PCI 3 , PBr 3 or POCI 3 , or a mixture of PCI 5 and POCI 3 .
  • Typical conditions include the use of a sub- stoichiometric, equimolar or excess amount of PCI 5 in POCI 3 relative to the compound of formula (lie), where POCI 3 itself may be present in an equimolar amount or alternatively, be used in a sub-stoichiometric amount or excess relative to the compound of formula (lie).
  • halogenation of hydroxamic acid ester of formula (lie) can be done without a solvent in certain cases or, preferentially, in the presence of a solvent or mixture of solvents. Any organic solvent that is inert under the specific reaction conditions can be chosen.
  • Preferred solvents include the following, without limiting the selection: aliphatic or aromatic hydrocarbons that may optionally be substituted by one or several halogen atoms such as pentane, hexanes, heptanes, cyclohexane, petroleum ether, benzene, toluene, xylene, chlorobenzene, dichlorobenzenes, dichloromethane, chloroform, 1,2-dichloroethane, carbon tetrachloride, ethers such as diethylether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, tetrahydrofuran, 1,4- dioxane, dimethoxyethane, triethylene glycol dimethyl ether (methyltriglyme), or acetonitrile, propionitrile, benzonitrile or a substituted benzonitrile.
  • halogen atoms such as pentane,
  • catalysts to facilitate this type of reaction comprising the use of catalysts such as dimethylformamide, diethylformamide and formylpiperidine.
  • reaction temperature can be varied over a wide range. Typical reaction temperatures vary between - 100°C and 250°C. Preferentially, the temperature range is between 0°C and 100°C. On some occasions, the reaction may be carried out under reflux.
  • This transformation can also optionally be carried out under ultrasonication.
  • Typical bases include the following without limiting the selction: Triethylamine, tripropylamine, tributylamine, di-isopropyl-ethylamine, ⁇ , ⁇ -dimethyl-cyclohexylamine, N-methyl- dicyclohexylamine, ⁇ , ⁇ -dimethyl-aniline, N,N-d iethyl-aniline, ⁇ , ⁇ -dimethyl-benzylamine, N,N- diethyl-benzylamine, pyridine, 2-methyl-pyridine, 3-methyl-pyridine, 4-methyl-pyridine, 2,6- dimethyl-pyridine, 2,4,6-trimethyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, N- ethy
  • Compounds of formula (lie) can be formed by reacting compounds of formula (lib) with a hydroxamic acid derivative of formula (XV) wherein R 37 is as defined herein for compounds of formula (lid). This transformation is an alkylation of the hydroxamic acid derivative (XV) or its salt generated in situ by the action of a base.
  • Ketones of formula (IVa 7 ), that is a compound of formula (IVa) wherein D 1 is N may be obtained by acidic hydrolysis methods, well known to the person skilled in the art from compounds of formula (XVIa), that is a compound of formula (XVI) wherein D 1 is N.
  • Enolethers of formula (XVIa) can be obtained by reacting enaminones of formula (XVIII) wherein G 1 , G 2 , G 3 and p are as described herein for compounds of formula (I) and R 38 represents hydrogen, CO-CH 3 , CO-CH 2 CH 3 , CO-CH 2 CH 2 CH 3 , CO-CH(CH 3 ) 2 , CO-CF 3 , CO-CF 2 CF 3 , CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 or CH(CH 3 ) 2 with amidines or guanidines of formula (XVII) wherein Y 1 is as described herein for compounds of formula (I).
  • condensation reactions can be performed using a number of conditions well known to the person skilled in the art. Such reactions are carried out in the presence of a base preferentially sodium or potassium alcoholate in ethanol or methanol. Specific reaction conditions may be found in Synthesis, 1012-1018, 1996; J. Heterocycl. Chem. 20, 649-653, 1983 or in WO2009010488.
  • Enaminones of formula (XVIII) can be obtained by reacting ketone of formula (XX) wherein G 1 , G 2 , G 3 and p are as described herein for compounds of formula (I) and R 38 represents hydrogen, CO-CH 3 , CO-CH 2 CH 3 , CO-CH 2 CH 2 CH 3 , CO-CH(CH 3 ) 2 , CO-CF 3 , CO-CF 2 CF 3 , CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 or CH(CH 3 ) 2 with ⁇ , ⁇ -dimethylformamide dialkyl acetal of formula (XIX) wherein R 39 represents d-C 4 alkyl.
  • condensation reactions are well known to the person skilled in the art.
  • the reaction is carried out in an inert solvent or without solvent at temperatures ranging from 0°C to 250°C preferably between 50 and 160°C.
  • Specific reaction conditions may be found in Synthesis, (97), 3397, 1964; Synthesis, (97), 3407, 1964; Journal of Med. Chem., Vol. 52, No. 16, 5152-5163; Tetrahedron Lett, (27), 2567, 1986; Tetrahedron Lett, (50), 2255-2264, 1994; Synthetic Commun., (28), 10, 1743-1753, 1998 or in Chem. Ber., (104), 2975, 1971.
  • Enol ethers of formula (XX) can be obtained by reacting ketones of formula (XXII) wherein G 1 , G 2 , G 3 and p are as described herein for compounds of formula (I) with an alcohol of formula (XXI) wherein R 38 represents hydrogen, CO-CH 3 , CO-CH 2 CH 3 , CO-CH 2 CH 2 CH 3 , CO- CH(CH 3 ) 2 , CO-CF 3 , CO-CF 2 CF 3 , CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 or CH(CH 3 ) 2 .
  • Such reactions can be affected using a number of conditions well known to the person skilled in the art. Specific reaction conditions may be found in WO2004104007.
  • the reaction may be performed in the presence or absence of an inert organic or inorganic solvent, or in the presence of a mixture of such solvents. Preferentially, it is performed in the presence of one or more solvents.
  • Preferred solvents include the following aliphatic or aromatic hydrocarbons, which may optionally be substituted by one or more halogen atoms, such as pentane, hexanes, heptanes, cyclohexane, petroleum ether, benzene, toluene, xylene, chlorobenzene, dichlorobenzenes, dichloromethane, chloroform, 1,2-dichloroethane or carbon tetrachloride, ethers such as diethylether, diisopropyl ether, tert-butyl methyl ether,
  • ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone or methyl isobutyl ketone
  • acids and ester such as acetic acid, ethyl acetate or methyl acetate
  • aprotic polar solvents such as acetonitrile, pripionitril, dimethyl formamide, dimethyl acetamide, N-methyl-pyrrolidone, dimethyl sulfoxide, sulfolane, DMPU, or pyridine and picolines.
  • solvents includes water and alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert- butanol, pentanol, isopentanol, hexanol, trifluorethanol, ethylene glycol or methoxyethanol.
  • alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert- butanol, pentanol, isopentanol, hexanol, trifluorethanol, ethylene glycol or methoxyethanol.
  • the reaction may be performed between -20°C and 250°C, preferentially between 0°C and
  • reaction mixture may be heated to reflux.
  • compounds can be used in the form of the free compound, or, alternatively, they can be used in the form of a salt such as the acetate, trifluoroacetate, propionate, benzoate, oxalate, methylsolfonate, phenylsulfonate, p-tolylsulfonate,
  • the reaction can be carried out in the absence of an acid using the free compounds.
  • reaction may be performed in the presence of an acid in catalytic,
  • Acids that could be used include acetic acid, propionic acid, oxalic acid, trifluoroacetic acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, methansulfonic acid, para-toluenesulfonic acid, sulphuric acid, sodium hydrogensulphate and phosphoric acid.
  • the reaction can optionally be carried out in a water-free solvent system in the presence of a drying agent, such as sodium or magnesium sulphate, potassium carbonate or molecular sieves.
  • the condensation reaction can lead to a mixture of the E- and the Z- oxime (ether) product.
  • the condensation product may also be exclusively either the E- or the Z- oxime (ether).
  • Condensations can be performed under reduced pressure, normal pressure or increased pressure. Preferentially the reaction is performed under normal pressure.
  • the reaction may be performed in the absence or presence of a solvent or a mixture of solvents.
  • Preferential solvents include the following aliphatic or aromatic hydrocarbons that may optionally be substituted by one or more halogen atoms such as pentane, hexanes, heptanes, cyclohexane, petroleum ether, benzene, toluene, xylene, chlorobenzene, dichlorobenzenes, dichloromethane, chloroform, 1,2-dichloroethanev or carbon tetrachloride, ethers such as diethyl ether, diisopropyl ether, tert-butyl-methyl ether, tetrahydrofuran, 1,4-dioxane, dimethoxyethane or diglycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone or methyl isobutyl
  • the selction of solvents includes also water and alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol, pentanol, isopentanol, hexanol, trifluorethanol, ethylene glycol or methoxyethanol.
  • alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol, pentanol, isopentanol, hexanol, trifluorethanol, ethylene glycol or methoxyethanol.
  • the reaction may be performed in a biphasic system comprising an organic solvent that is not miscible with water, such as toluene, dichloromethane, dichloro-ethylene, and an aqueous solvent, such as water.
  • a phase-transfer catalyst such as tetra-n-butylammonium bromide (TBAB), Tetradecyldimethylbenzylammonium chloride (TDMBAC), N-Benzyltrimethylammonium hydroxide, along with aqueous sodium or potassium hydroxide in stoichiometric amounts.
  • TBAB tetra-n-butylammonium bromide
  • TDMBAC Tetradecyldimethylbenzylammonium chloride
  • N-Benzyltrimethylammonium hydroxide N-Benzyltrimethylammonium hydroxide
  • the reaction may be carried out at temperatures varying from -100°C and 250°C.
  • the temperature range is between 0°C and 100°C.
  • an organic or inorganic base may be present such as alkali- and earth alkali acetates, amides, carbonates, hydrogencarbonates, hydrides, hydroxides or alcoholates such as sodium, potassium, caesium or calcium acetate, sodium, potassium, caesium or calcium carbonate, sodium, potassium, caesium or calcium hydrogencarbonate, sodium, potassium, caesium or calcium hydride, sodium, potassium, caesium or calcium amide, sodium, potassium, caesium or calcium hydroxide, sodium, potassium, caesium or calcium methanolate, sodium, potassium, caesium or calcium ethanolate, sodium, potassium, caesium or calcium n-, i-, s- or t- butanolate, triethylamine, tripropylamine, tributylamine, di-isopropyl-ethylamine, N,N-dimethyl- cyclohexylamine, N-methyl-dicyclohexyl
  • the alkylation can be performed under reduced pressure, normal pressure or increased pressure. Preferentially the reaction is performed under normal pressure.
  • steps 1) to 19) may be required to be purified using, for example, chromatography, crystallisation or other purification techniques well known to the person skilled in the art.
  • the compounds of formula (I) to formula (XXII) and, where appropriate, the tautomers thereof, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.
  • the invention therefore also relates to a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a compound of formula (I) is applied as active ingredient to the plants, to parts thereof or the locus thereof.
  • the compounds of formula (I) according to the invention are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and are used for protecting numerous useful plants.
  • the compounds of formula (I) can be used to inhibit or destroy the diseases that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.
  • compounds of formula (I) as dressing agents for the treatment of plant propagation material, in particular of seeds (fruit, tubers, grains) and plant cuttings (e.g. rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.
  • the compounds of formula (I) according to the invention may be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage or in hygiene management.
  • the compounds of formula (I) are, for example, effective against the phytopathogenic fungi of the following classes: Fungi imperfecti (e.g. Botrytis, Pyricularia, Helminthosporium,
  • Basidiomycetes e.g. Rhizoctonia, Hemileia, Puccinia. Additionally, they are also effective against the Ascomycetes classes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and of the Oomycetes classes (e.g.
  • useful plants to be protected typically comprise the following species of plants: cereal (wheat, barley, rye, oat, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit
  • useful plants is to be understood as including also useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • herbicides like bromoxynil or classes of herbicides
  • EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors
  • GS glutamine synthetase
  • PPO protoporphyrinogen-oxidase
  • Crola Clearfield® summer rape
  • crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names
  • useful plants is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin- producing bacteria, especially those of the genus Bacillus.
  • YieldGard® (maize variety that expresses a CrylA(b) toxin); YieldGard Rootworm® (maize variety that expresses a CrylllB(bl) toxin); YieldGard Plus® (maize variety that expresses a CrylA(b) and a CrylllB(bl) toxin); Starlink® (maize variety that expresses a Cry9(c) toxin); Herculex I® (maize variety that expresses a CryIF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylA(c) toxin);
  • Bollgard I® (cotton variety that expresses a CrylA(c) toxin); Bollgard II® (cotton variety that expresses a CrylA(c) and a CryllA(b) toxin); VIPCOT® (cotton variety that expresses a VIP toxin); NewLeaf® (potato variety that expresses a CrylllA toxin); NatureGard® Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Btll corn borer (CB) trait), Agrisure® RW (corn rootworm trait) and Protecta®.
  • useful plants is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so- called “pathogenesis-related proteins” (PRPs, see e.g. EP-A-0 392 225).
  • PRPs pathogenesis-related proteins
  • Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818, and EP-A-0 353 191.
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • locus of a useful plant as used herein is intended to embrace the place on which the useful plants are growing, where the plant propagation materials of the useful plants are sown or where the plant propagation materials of the useful plants will be placed into the soil.
  • An example for such a locus is a field, on which crop plants are growing.
  • plant propagation material is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably "plant propagation material” is understood to denote seeds.
  • the compounds of formula (I) can be used in unmodified form or, preferably, together with carriers and adjuvants conventionally employed in the art of formulation.
  • the invention also relates to compositions for controlling and protecting against phytopathogenic microorganisms, comprising a compound of formula (I) and an inert carrier, and to a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a composition, comprising a compound of formula (I) as acitve ingredient and an inert carrier, is applied to the plants, to parts thereof or the locus thereof.
  • compounds of formula (I) and inert carriers are conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances.
  • the methods of application such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • the compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
  • Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.
  • the compounds of formula (I) or compositions, comprising a compound of formula (I) as active ingredient and an inert carrier can be applied to the locus of the plant or plant to be treated, simultaneously or in succession with further compounds.
  • further compounds can be e.g. fertilizers or micronutrient donors or other preparations which influence the growth of plants. They can also be selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
  • a preferred method of applying a compound of formula (I), or a composition, comprising a compound of formula (I) as active ingredient and an inert carrier is foliar application.
  • the frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen.
  • the compounds of formula (I) may also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field.
  • the compounds of formula (I) may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
  • a formulation i.e. a composition comprising the compound of formula (I) and, if desired, a solid or liquid adjuvant, is prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface-active compounds (surfactants).
  • extenders for example solvents, solid carriers and, optionally, surface-active compounds (surfactants).
  • the agrochemical formulations will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the compound of formula (I), 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant.
  • Advantageous rates of application are normally from 5g to 2kg of active ingredient (a.i.) per hectare (ha), preferably from lOg to 1kg a.i. /ha, most preferably from 20g to 600g a.i./ha.
  • convenient rates of application are from lOmg to lg of active substance per kg of seeds.
  • the rate of application for the desired action can be determined by experiments. It depends for example on the type of action, the developmental stage of the useful plant, and on the application (location, timing, application method) and can, owing to these parameters, vary within wide limits.
  • the compounds of formula (I), or a pharmaceutical salt thereof, described above may also have an advantageous spectrum of activity for the treatment and/or prevention of microbial infection in an animal.
  • Animal can be any animal, for example, insect, mammal, reptile, fish, amphibian, preferably mammal, most preferably human.
  • Treatment means the use on an animal which has microbial infection in order to reduce or slow or stop the increase or spread of the infection, or to reduce the infection or to cure the infection.
  • prevention means the use on an animal which has no apparent signs of microbial infection in order to prevent any future infection, or to reduce or slow the increase or spread of any future infection.
  • a compound of formula (I) in the manufacture of a medicament for use in the treatment and/or prevention of microbial infection in an animal.
  • a compound of formula (I) as a pharmaceutical agent.
  • a compound of formula (I) as an antimicrobial agent in the treatment of an animal.
  • a pharmaceutical composition comprising as an active ingredient a compound of formula (I), or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable diluent or carrier. This composition can be used for the treatment and/or prevention of antimicrobial infection in an animal.
  • This pharmaceutical composition can be in a form suitable for oral administration, such as tablet, lozenges, hard capsules, aqueous suspensions, oily suspensions, emulsions dispersible powders, dispersible granules, syrups and elixirs.
  • this pharmaceutical composition can be in a form suitable for topical application, such as a spray, a cream or lotion.
  • this pharmaceutical composition can be in a form suitable for parenteral administration, for example injection.
  • parenteral administration for example injection.
  • composition can be in inhalable form, such as an aerosol spray.
  • the compounds of formula (I) may be effective against various microbial species able to cause a microbial infection in an animal.
  • microbial species are those causing Aspergillosis such as Aspergillus fumigatus, A. flavus, A. terms, A. nidulans and A. niger, those causing Blastomycosis such as Blastomyces dermatitidis; those causing Candidiasis such as Candida albicans, C. glabrata, C. tropicalis, C. parapsilosis, C. krusei and C.
  • Aspergillosis such as Aspergillus fumigatus, A. flavus, A. terms, A. nidulans and A. niger
  • Blastomycosis such as Blastomyces dermatitidis
  • Candidiasis such as Candida albicans, C. glabrata, C. tropicalis, C. parapsilosis, C.
  • Microsporum Spp Trichophyton Spp, Epidermophyton Spp, Mucor Spp, Sporothorix Spp, Phialophora Spp, Cladosporium Spp, Petriellidium spp, Paracoccidioides Spp and Histoplasma Spp.
  • compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
  • the compound of formula I (herein after abbreviated by the term "TX” thus means a compound encompassed by the compounds of formula I, or preferably the term “TX” refers to a compound selected from the Tables 1-7 or Table 9) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide (insect, acarine, mollusc and nematode pesticide), fungicide, synergist, herbicide, safener or plant growth regulator where appropriate.
  • a pesticide insect, acarine, mollusc and nematode pesticide
  • fungicide fungicide
  • synergist synergist
  • herbicide herbicide
  • safener plant growth regulator
  • An additional active ingredient may: provide a composition having a broader spectrum of activity or increased persistence at a locus; provide a composition demonstrating better plant/crop tolerance by reducing phytotoxicity; provide a composition controlling insects in their different development stages; synergise the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the TX; or help to overcome or prevent the development of resistance to individual components.
  • suitable pesticides include the following:
  • a) Pyrethroids such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, s-bioallethrin, fenfluthrin, prallethrin or 5-benzyl-3-furylmethyl-(E)-(lR,3S)-2,2-dimethyl- 3-(2-oxothiolan-3-ylidenemethyl)cyclopropane carboxylate;
  • Organophosphates such as, profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl,
  • Carbamates including aryl carbamates
  • pirimicarb triazamate
  • cloethocarb carbofuran
  • furathiocarb furathiocarb
  • ethiofencarb aldicarb
  • thiofurox carbosulfan
  • bendiocarb fenobucarb
  • propoxur methomyl or oxamyl
  • Benzoyl ureas such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron or chlorfluazuron;
  • Organic tin compounds such as cyhexatin, fenbutatin oxide or azocyclotin;
  • Macrolides such as avermectins or milbemycins, for example abamectin, emamectin benzoate, ivermectin, milbemycin, or spinosad, spinetoram or azadirachtin;
  • Organochlorine compounds such as endosulfan, benzene hexachloride, DDT, chlordane or dieldrin;
  • Amidines such as chlordimeform or amitraz
  • Fumigant agents such as chloropicrin, dichloropropane, methyl bromide or metam
  • Neonicotinoid compounds such as imidacloprid, thiacloprid, acetamiprid, clothianidin, nitenpyram, dinotefuran or thiamethoxam;
  • Diacyl hydrazines such as tebufenozide, chromafenozide or methoxyfenozide;
  • Diphenyl ethers such as diofenolan or pyriproxifen
  • pesticides having particular targets may be employed in the composition, if appropriate for the intended utility of the composition.
  • selective insecticides for particular crops for example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such as buprofezin) for use in rice may be employed.
  • insecticides or acaricides specific for particular insect species/stages may also be included in the compositions (for example acaricidal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or tetradifon; acaricidal motilicides, such as dicofol or propargite; acaricides, such as bromopropylate or chlorobenzilate; or growth regulators, such as hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron).
  • acaricidal ovo-larvicides such as clofentezine, flubenzimine, hexythiazox or tetradifon
  • acaricidal motilicides such as dicofol or propargite
  • acaricides such as bromopropylate or chlorobenzilate
  • growth regulators such
  • TX refers to a compound covered by the compounds of formula I or preferably the term “TX” refers to a compound selected from the Tables 1 to 9 and the following List shows specific examples of mixtures comprising the component TX and the component (B):
  • an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,
  • an acaricide selected from the group of substances consisting of l,l-bis(4-chlorophenyl)-2- ethoxyethanol (IUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-/V-methyl-/V-l-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981) + TX, abamectin (1) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha-cypermethrin (202) + TX, amidithion (870) + TX, amidoflumet [CCN
  • polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX, promacyl (1354) + TX, propargite (671) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridaphenthion (701) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, quinalphos (711) + TX, quintiofos (1381) + TX, R-1492 (development code
  • development code (development code) (1383) + TX, rotenone (722) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, sophamide (1402) + TX, spirodiclofen (738) + TX, spiromesifen (739) + TX, SSI-121 (development code) (1404) + TX, sulfiram (alternative name) [CCN] + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulphur (754) + TX, SZI-121 (development code) (757) + TX, tau- fluvalinate (398) + TX, tebufenpyrad (763) + TX, TEPP (1417) + TX, terbam
  • an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX,
  • an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomate (1011) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX,
  • an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX,
  • a bactericide selected from the group of substances consisting of l-hydroxy-lH-pyridine-2- thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1105) + TX, dodicin (1112) + TX, fenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrargaphen (alternative name) [CCN] + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX
  • a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Hopkins (scientific name) (5
  • israeltaki (scientific name) (51) + TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii (alternative name) (54) + TX, Chrysoperla carnea (alternative name) (151) + TX, Cryptolaemus
  • montrouzieri (alternative name) (178) + TX, Cydia pomoneiia GV (alternative name) (191) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternative name) (300) + TX, Helicoverpa zea NPV (alternative name) (431) + TX, Heterorhabditis bacteriophora and H.
  • a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX,
  • a chemosterilant selected from the group of substances consisting of apholate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzid [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and
  • an insect pheromone selected from the group of substances consisting of (£)-dec-5-en-l-yl acetate with (£)-dec-5-en-l-ol (IUPAC name) (222) + TX, (£)-tridec-4-en-l-yl acetate (IUPAC name) (829) + TX, (£)-6-methylhept-2-en-4-ol (IUPAC name) (541) + TX, (E,Z)-tetradeca-4, 10- dien-l-yl acetate (IUPAC name) (779) + TX, (Z)-dodec-7-en-l-yl acetate (IUPAC name) (285) + TX, (Z)-hexadec-ll-enal (IUPAC name) (436) + TX, (Z)-hexadec-ll-en-l-yl acetate (IUPAC name) (437) + TX, (Z)-hexadec-13-en
  • an insecticide selected from the group of substances consisting of 1-dichloro-l-nitroethane (IUPAC/Chemical Abstracts name) (1058) + TX, l,l-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056), + TX, 1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX, l-bromo-2- chloroethane (IUPAC/Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-l-(3,4-dichloro- phenyl)ethyl acetate (IUPAC name) (1451) + TX, 2,2-dichlorovinyl 2-ethylsulphinylethyl methyl phosphate (IUPAC name) (1066) + TX, 2-
  • ethylphosphonothioate (1057) + TX, 0,0-diethyl 0-4-methyl-2-oxo-2H-chromen- 7-yl phosphorothioate (IUPAC name) (1074) + TX, ⁇ , ⁇ -diethyl 0-6-methyl-2-propylpyrimidin-4- yl phosphorothioate (IUPAC name) (1075) + TX, ⁇ , ⁇ , ⁇ ', O'-tetrapropyl dithiopyrophosphate (IUPAC name) (1424) + TX, oleic acid (IUPAC name) (593) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydemeton-methyl (609) + TX, oxydeprofos (1324) + TX, oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, para-dichlorobenzen
  • TX sodium hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623) + TX, sodium selenate (IUPAC name) (1401) + TX, sodium thiocyanate [CCN] + TX, sophamide (1402) + TX, spinosad (737) + TX, spiromesifen (739) + TX, spirotetrmat (CCN) + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulphuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb
  • teflubenzuron (768) + TX, tefluthrin (769) + TX, temephos (770) + TX, TEPP (1417) + TX, terallethrin (1418) + TX, terbam (alternative name) + TX, terbufos (773) + TX,
  • a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloethocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + T
  • a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, l,2-dibromo-3-chloropropane (IUPAC/Chemical Abstracts name) (1045) + TX, 1,2- dichloropropane (IUPAC/ Chemical Abstracts name) (1062) + TX, 1,2-dichloropropane with 1,3- dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4- dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/Chemical Abstracts name) (1065) + TX, 3-(4- chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-l,3,5- thiadiazinan-3-ylacetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (
  • a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX,
  • a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract
  • a rodenticide selected from the group of substances consisting of 2-isovalerylindan-l,3- dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminium phosphide (640) + TX, antu (880) + TX, arsenous oxide (882) + TX, barium carbonate (891) + TX, bisthiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coumafuryl (
  • a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934) + TX, 5-(l,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX,
  • an animal repellent selected from the group of substances consisting of anthraquinone (32)
  • TX chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4-amine (IUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX, a virucide selected from the group of substances consisting of imanin (alternative name)
  • a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octhilinone (590) and thiophanate-methyl (802) + TX,
  • azaconazole 60207-31-0] + TX, bitertanol [70585-36-3] + TX, bromuconazole [116255-48-2] + TX, cyproconazole [94361-06-5] + TX, difenoconazole [119446-68-3] + TX, diniconazole [83657-24- 3] + TX, epoxiconazole [106325-08-0] + TX, fenbuconazole [114369-43-6] + TX,
  • TX isoprothiolane [50512-35-1] + TX, phosdiphen [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos-methyl [57018-04-9] + TX, acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, benthiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, chinomethionat [2439-01-2] + TX, chloroneb [2675-77-6] + TX, chlorothalonil [1897-45-6] + TX, cyflufenamid [180409-60-3] + TX, cymoxanil [57966-95-7] + TX, dichlone [117-80-6] + TX, diclocymet [139920-32-4] + TX
  • the components (B) are known.
  • the references in brackets behind the active ingredients, e.g. [3878-19-1] refer to the Chemical Abstracts Registry number.
  • the above described mixing partners are known.
  • the active ingredients are included in "The Pesticide Manual” [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; The British Crop Protection Council]
  • they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound “abamectin” is described under entry number (1).
  • [CCN] is added hereinabove to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible on the internet under the internet address
  • the compound of the formula I is preferably a compound selected from the Tables 1-7 or Table 9; more preferably Table 9;
  • the mixing ratios can vary over a large range and are, preferably 100: 1 to 1:6000, especially 50: 1 to 1:50, more especially 20: 1 to 1:20, even more especially 10: 1 to 1: 10.
  • Those mixing ratios are understood to include, on the one hand, ratios by weight and also, on other hand, molar ratios.
  • mixtures can advantageously be used in the above-mentioned formulations (in which case "active ingredient” relates to the respective mixture of TX with the mixing partner).
  • Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type.
  • other formulation types may be prepared.
  • one active ingredient is a water insoluble solid and the other a water insoluble liquid
  • the resultant composition is a suspoemulsion (SE) formulation.
  • the mixtures comprising a TX selected from Tables 1-7 or Table 9 and one or more active ingredients as described above can be applied, for example, in a single "ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • the order of applying the compounds of formula I selected from Tables 1-7 or Table 9 and the active ingredients as described above is not essential for working the present invention.
  • Step B) A 50 mL single-necked round-bottom flask equipped with a condenser was charged with a solution of 2-methyl-5,6,7,8-tetrahydro-quinolin-4-ol (4.00 g) in phosphorus oxide chloride (18.3 mL) under an argon atmosphere. The resulting colourless solution was stirred at 100°C for 3.5 hours, after which time TLC indicated that no starting material was remaining. The solvent was removed in vacuo and hot water (40-50°C) was added carefully and slowly to the residue to hydrolyse the remaining phosphorus oxide chloride. Under cooling with an ice- water cooling bath, the pH was adjusted to 12 by the addition of 4 M aqueous NaOH.
  • Step C A 25 mL single-necked round-bottom flask equipped with a condenser was charged with a solution of 4-chloro-2-methyl-5,6,7,8-tetrahydroquinoline (560 mg) in acetic anhydride (0.49 mL). Under stirring, benzaldehyde (0.34 mL) was added and the resulting yellow solution was stirred under heating to reflux for 3.5 hours. Following the course of the reaction by TLC indicated that starting material was consumed by this time. The resulting brown solution was cooled to room temperature. Crushed ice was added and the pH was adjusted to 10 using a small amount of 2 M aqueous NaOH. Extraction was carried out using ethyl acetate (2x20 mL).
  • Step A A 5 mL microwave tube was charged with a solution of 4-chloro-2-methyl-5,6,7,8- tetrahydroquinoline (500 mg) in 1,2-dichloroethane (2.50 mL). Under stirring, trimethylboroxine (380 mg), potassium carbonate (647 mg) and dichloro[l,l'-bis(diphenylphosphino)ferrocene] palladium(II) dichloromethane adduct (101 mg) were added and the resulting red suspension was degassed under argon for 5 minutes. The reaction mixture was subjected to microwave irradiation at 120°C for 0.5 hour.
  • Step C A 25 mL single-necked round-bottom flask equipped with a condenser was charged with a solution of 2,4-dimethyl-5,6,7,8-tetrahydro-quinoline-l-oxide (334 mg) in
  • Step D A 25 mL single-necked round-bottom flask equipped with a condenser was charged with a solution of 2,4-dimethyl-5,6,7,8-tetrahydro-quinolin-8-ol (226 mg) in chloroform (2.00 mL). Under stirring, manganese(IV) oxide (443 mg) was added and the resulting black suspension was stirred under heating to reflux for 18 hours, after which time TLC indicated that no starting material was remaining. The resulting black material was purified by chromatography on silica gel (eluent: heptane / ethyl acetate gradient from 1:1 to 1:2 (v:v)). This gave the tittle compound (78 mg) as an orange gum.
  • Step A) 9-Methyl-l,2,3,4-tetrahydroacridine In a round-bottom flask, cyclohexanone (6.1 mL, 58 mmol) was heated at 90°C, and 2-aminoacetophenone hydrochloride (10 g; 58 mmol) was added by small fractions. The bottom flask was then equipped with a condenser, and the crude heterogeneous mixture was further heated overnight at 110°C. After cooling to room temperature, the red-orange solid was dissolved in ethanol/HCI (12 N) [95/5 v/v]. The solution was then neutralized with an aqueous NaOH solution.
  • Step B) N xide-9-methyl-l,2,3,4-tetrahydroacridine A dichloromethane solution (300 mL) of 3-chloroperbenzoic acid (26 g, 105 mmol) was slowly added to a dichloromethane solution (100 mL) of 9-methyl-l,2,3,4-tetrahydroacridine (10.2 g, 52 mmol) at 0°C. The mixture was stirred for 4 h at room temperature and quenched with an aqueous NaOH solution. The organic layers were further washed with water (5 x 100 mL) and dried over MgS0 4 , and the solvent was removed under reduced pressure giving desired product as a brownish solid.
  • the crude solid was dissolved in methanol (50 mL) and saponified by an aqueous K 2 C0 3 solution (2 M, 150 mL); a brown solid precipitated.
  • the methanol was removed under reduced pressure, and the product was extracted with dichloromethane (2 x 150 mL).
  • the combined organic layers were washed with brine (2 x 50 mL), dried over magnesium sulfate, and evaporated to dryness.
  • the desired product was recovered as a brown solid (9.4 g, 84%).
  • Step D) 9-methyl-2,3-dihydro-lH-acridin-4-one To a dichloromethane solution (300 mL) of
  • HP 1100 HPLC from Agilent solvent degasser, binary pump, heated column compartment and diode-array detector.
  • HP 1100 HPLC from Agilent solvent degasser, quaternary pump (ZCQ) / binary pump (ZDQ), heated column compartment and diode-array detector.
  • Type of column Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron; Temperature: 60°C.
  • Ionization method Electrospray; Polarity: positive and negative ions; Capillary (kV): 3.00; Cone (V): 30.00; Extractor (V): 2.00; Source Temperature (°C): 100; Desolvation Temperature (°C): 250; Cone Gas Flow (L/Hr): 50; Desolvation Gas Flow (L/Hr): 400; Mass range: 100 to 900 Da
  • Solvent degasser binary pump, heated column compartment and diode-array detector; Column: Phenomenex Gemini C18, 3 - m, 30 x 3 mm; Temp: 60°C; DAD Wavelength range (nm): 210 to 500;
  • Solvent degasser binary pump, heated column compartment and diode-array detector.
  • Wheat leaf segments cultivated variety (cv) Kanzler were placed on agar in 24-well plates and sprayed with formulated test compound diluted in water at an application rate of 200ppm.
  • the leaf disks were inoculated with a spore suspension of the fungus 1 day after application.
  • the inoculated leaf segments were incubated at 19°C and 75% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7 - 9 days after application).
  • the following compounds gave at least 80% control of Puccinia recondita f. sp. tritici: P.01, P.02, P.04, P.05, P.06, P.08, P.09. P.20, P.23, P.27, P.28, P.29, P.30.
  • Wheat leaf segments cv Kanzler were placed on agar in 24-well plates. The leaf segments were inoculated with a spore suspension of the fungus. The plates were stored in darkness at 19°C and 75% relative humidity. The formulated test compound diluted in water was applied at an application rate of 200ppm 1 day after inoculation. The leaf segments were incubated at 19°C and 75% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6 - 8 days after application). The following compounds gave at least 80% control of Puccinia recondita f. sp. tritici: P.01, P.02, P.04, P.05, P.06, P.08, P.09, P.11. P.20, P.23, P.27, P.28, P.29.
  • Phaeosphaeria nodorum (Seotoria nodorum) / wheat / leaf disc preventative (Glume blotch):
  • Wheat leaf segments cv Kanzler were placed on agar in a 24-well plate and sprayed with formulated test compound diluted in water at an application rate of 200ppm.
  • the leaf disks are inoculated with a spore suspension of the fungus 2 days after application.
  • the inoculated test leaf disks are incubated at 20°C and 75% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (5 - 7 days after application).
  • Phaeosphaeria nodorum The following compounds gave at least 80% control of Phaeosphaeria nodorum: P.01, P.02, P.04, P.05, P.06, P.08, P.09, P.ll, P.14, P.16, P.17, P.18P.19, P.20, P.21, P.22, P.23, P.27, P.28, P.29, P.30.
  • Barley leaf segments cv Hasso are placed on agar in a 24-well plate and sprayed with formulated test compound diluted in water at an application rate of 200ppm.
  • the leaf segments are inoculated with a spore suspension of the fungus two days after application of the test solution.
  • the inoculated leaf segments are incubated at 20°C and 65% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound is assessed as disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (5 - 7 days after application).
  • Tomato leaf disks cv Baby are placed on agar in 24-well plates (24-well format) and sprayed with the formulated test compound diluted in water at an application rate of 200ppm.
  • the leaf disks are inoculated with a spore suspension of the fungus 2 days after application.
  • the inoculated leaf disks are incubated at 23°C/21°C (day/night) and 80% relative humidity under a light regime of 12/12 h (light/dark) in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check disk leaf disks (5 - 7 days after application).
  • the following compounds gave at least 80% control of Alternaria solani: P.08,P.29.
  • Mycelia fragments and oospores of a newly grown liquid culture of the fungus were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96 well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal mycelia/spore mixture was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 2-3 days after application. The following compounds gave at least 80% control of Pythium ultimum: P.08,P.27, P.28.
  • Botryotinia fuckeliana Botryotis cinerea I liquid culture (Gray mould):
  • Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (Vogels broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 3-4 days after application.
  • the following compounds gave at least 80% control of Botryotinia fuckeliana: P.01, P.02, P.03, P.04, P.05, P.06, P.07, P.09, P.10, P. ll, P.12, P.14, P.15. P.18, P.19, P.20, P.21, P.22, P.23, P.27, P.28, P.29, P.30, P.31.
  • Glomerella lagenarium (Colletotrichum lagenarium) / liquid culture (Anthracnose) :
  • Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth is measured photometrically 3-4 days after application. The following compounds gave at least 80% control of Glomerella lagenarium: P.01, P.02, P.03, P.04, P.06, P.08, P.09, P.ll, P.14, P.15. P.22, P.23, P.27, P.28, P.29, P.30.
  • Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal spores was added. The test plates are incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application.
  • the following compounds gave at least 80% control of Mycosphaerella arachidis: P.01, P.02, P.03, P.04, P.05, P.06, P.08, P.09, P.10, P. ll, P.12, P.14, P.15. P.18, P.20, P.21, P.22, P.23, P.27, P.28, P.29, P.31.
  • Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application.
  • the following compounds gave at least 80% control of Mycosphaerella graminicola: P.01, P.02, P.03, P.04, P.06, P.08, P.09, P.10, P.ll, P.12, P.14, P.15. P.18, P.19, P.20, P.21, P.22, P.23, P.27, P.28, P.29, P.30, P.31.
  • Gaeumannomyces graminis I liquid culture (Take-all of cereals):
  • Mycelial fragments of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96- well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal spores is added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application. The following compounds gave at least 80% control of Gaeumannomyces graminis: P.01, P.02, P.03, P.08, P.09, P. ll, P.14, P.15., P.20, P.21, P.22, P.23, P.27, P.31.
  • Thanatephorus cucumeris (Rhizoctonia solani) I liquid culture (foot rot, dampinq-off): Mycelia fragments of a newly grown liquid culture of the fungus are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of the test compounds into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal material was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 3-4 days after application. The following compounds gave at least 80% control of Thanatephorus cucumeris: P.01, P.02, P.04, P.06, P.08, P.09, P.14, P.15.
  • Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of test compound into a 96-well microtiter plate at an application rate of 200ppm, the nutrient broth containing the fungal spores was added. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically 4-5 days after application. The following compounds gave at least 80% control of Monographella nivalis: P.01, P.02, P.04, P.06, P.08, P.09. P.21, P.22, P.23,.28, P.29.
  • Wheat leaf segments cv. Kanzler were placed on agar in a 24-well plate and sprayed with the formulated test compound diluted in water at an application rate of 200ppm.
  • the leaf disks were inoculated by shaking powdery mildew infected plants above the test plates 1 day after application.
  • the inoculated leaf disks were incubated at 20°C and 60% relative humidity under a light regime of 24 h darkness followed by 12h/12h (dark/light) in a climate chamber and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6 - 8 days after application).
  • Mycelia fragments of a newly grown liquid culture of the fungus are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate at an application rate of 200ppm (96-well format) the nutrient broth containing the fungal material is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically 3-4 days after application. The following compounds gave at least 80% control of : _Sclerotinia sclerotiorum: P.04, P.06, P.09, P.15. P.23, P.27.
  • Rice leaf segments cv. Ballila are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water at an application rate of 200ppm.
  • the leaf segments are inoculated with a spore suspension of the fungus 2 days after application.
  • the inoculated leaf segments are incubated at 22°C and 80% rh under a light regime of 24 h darkness followed by 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (5 - 7 days after application).

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  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention porte sur des composés de formule (I) dans laquelle A, X, Y1, Y3, Y4, Y6, D1, D2, D3, G1, G2, G3 et p sont tels que définis dans les revendications. L'invention porte en outre sur des intermédiaires utilisés dans la préparation de ces composés, sur des compositions qui comprennent ces composés et sur leur utilisation en agriculture ou horticulture pour la lutte contre l'infestation de plantes par des microorganismes phytopathogènes, de préférence des champignons, ou la prévention de cette infestation.
PCT/EP2012/075712 2011-12-20 2012-12-17 Microbicides bisoximes cycliques WO2013092460A1 (fr)

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