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US 6,281,209 B1Granted
Fungicidal alkoximinomethyldioxazine derivatives
AssigneeBayer Aktiengesellschaft
InventorsPeter Gerdes, Herbert Gayer, Bernd-Wieland Krüger, Ulrich Heinemann, Bernd Gallenkamp, Ralf Tiemann, Stefan Dutzmann, Karl-Heinz Kuck, Klaus Stenzel
Life of this patent
Estimating the term…
Abstract
The invention relates to alkoximinomethyldioxazine compounds and intermediates thereof, and to process for the preparation of the alkoximinomethyldioxazine compounds and intermediates thereof. The alkoximinomethyldioxazine compounds have the structure:
Claims15
Compounds of the formula (I)
- in which
- R1 represents hydrogen, cyano or represents alkyl having 1 to 6 carbon atoms which is optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms or represents cycloalkyl having 3 to 8 carbon atoms which is optionally substituted by halogen, alkyl or alkoxy having in each case 1 to 4 carbon atoms,
- R2 represents hydrogen or represents alkyl having 1 to 6 carbon atoms which is optionally substituted by halogen or alkoxy having 1 to 4 carbon atoms or represents cycloalkyl having 3 to 8 carbon atoms which is optionally substituted by halogen, alkyl or alkoxy having in each case 1 to 4 carbon atoms,
- G represents a single bond, methanediyl, 1,1-ethanediyl, 1,2-ethanediyl, 1,1-, 1,2-, 1,3- or 2,2-propanediyl, 1,1-, 1,2-, 1,3-, 1,4-, 2,2-, 2,3-butanediyl or 1,1-, 1,2- or 1,3-(2-methyl-propanediyl), —O—CH2— (where Z is attached to the oxygen atom),
- Z
- represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of chlorine fluorine, bromine, cyano, hydroxyl, amino, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethyl-sulphinyl or trifluoromethylsulphonyl;
- represents phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cylohexyl, cycloheptyl, oxazolyl, benzofuranyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl or 5,6-dihydro-1,4,2-dioxazinyl, each of which is optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxy-carbonyl, ethoxycarbonyl,
- in each case doubly attached methylenedioxy, ethylenedioxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl and ethyl or a grouping,
- where
- A1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and
- A2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl and
- E1, E2, E3 and E4 are identical or different and, independently of one another each represents hydrogen, alkyl or hydroxyalkyl having in each case 1 to 4 carbon atoms or halogenoalkyl having 1 to 4 carbon atoms and 1 to five identical or different halogen atoms, or
- E1 and E2 or E1 and E3 or E3 and E4 together with the respective carbon atoms to which they are attached form a cycloaliphatic ring having five, six or seven carbon atoms and
- L1, L2, L3 and L4 are identical or different and, independently of one another, each represents hydrogen, halogen, cyano, nitro, represents alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms and being in each case optionally substituted by 1 to 5 halogen atoms.
12 more elements
Compounds of the formula (I)
- in which
- R1 represents hydrogen, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclobutyl,
- R2 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclobutyl,
- G represents a grouping
- in which
- R3
- represents hydrogen or represents methyl, ethyl, n- or i-propyl, n-, -1-, s- or t-butyl, each of which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, methoxy, ethoxy, (each of which is optionally substituted by fluorine and/or chlorine),
- represents allyl, crotonyl, 1 -methyl-allyl, propargyl or 1 -methyl-propargyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine;
- represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each of which is optionally mono- to hexasubstituted by fluorine, chlorine, bromine, methoxy, ethoxy, phenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy), methyl, ethyl, n- or i-propyl;
- represents benzyl, phenyl-1-ethyl or phenyl-2-ethyl, each of which is optionally mono- to trisubstituted in the phenyl moiety, where the possible substituents are preferably selected from the list below:
- Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i- s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorohloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl;
- in each case doubly attached trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, each of which is optionally mono- or polysubstituted by
- identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl,
- Z
- represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of chlorine fluorine, bromine, cyano, hydroxyl, amino, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorchloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl;
- represents vinyl, allyl or propargyl, each of which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of chlorine fluorine or bromine;
- or
- represents phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1,2-oxazolyl, benzofuranyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl or 5,6-dihydro-1,4,2-dioxazinyl, each of which is optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl,
- in each case doubly attached methylenedioxy, ethylenedioxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl or ethyl or a grouping
- where
- A1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and
- A2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl and
- E1, E2, E3 and E4 are identical or different and, independently of one another, each represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, hydroxymethyl, trifluoromethyl or trifluoroethyl, or
- E1 and E2 or E1 and E3 or E3 and E4 together with the respective carbon atoms to which they are attached form a cycloaliphatic ring having five, six or seven carbon atoms and
- L1, L2, L3 and L4 are identical or different and, independently of one another, each represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl.
23 more elements
Compounds of the formula (I)
- in which
- R1 represents methyl or cyclopropyl,
- R2 represents hydrogen,
- G represents a grouping
- in which
- R3 represents methyl or represents benzyl which is optionally mono- to trisubstituted in the phenyl moiety by fluorine, chlorine, bromine, cyano, nitro, methyl or methoxy,
- Z
- represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, trifluoroethyl, methoxymethyl, methylthiomethyl or methylsulphonylmethyl, vinyl, dichlorovinyl, allyl, propargyl, cyclopropyl, methylcyclopropyl, cyclobutyl, cyclopentyl, cylohexyl or represents 1,2-oxazolyl, benzofuranyl or, in particular, phenyl each of which is optionally mono- to trisubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
- fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethyisulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl,
- in each case doubly attached methylenedioxy, ethylenedioxy, each of which is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl and ethyl or a grouping,
- where
- A1 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and
- A2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-1-yl, 2-methyl-prop-1-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl,
- E1 and E2 are identical or different and, independently of one another, each represents hydrogen or methyl,
- E3 and E4 each represent hydrogen,
- L1 and L3 are identical or different and, independently of one another, each represents hydrogen or methyl and
- L2 and L4 each represent hydrogen.
14 more elements
Dependencies are inferred from the claim text.