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US 6,403,600 B1Granted
Methoximinophenylacetic acid amides
AssigneeBayer Aktiengesellschaft
InventorsFritz Maurer, Herbert Gayer, Peter Gerdes, Ulrich Heinemann, Bernd-Wieland Krüger, Robert Markert, Klaus Stenzel, Gerd Hänssler, Astrid Mauler-Machnik
Life of this patent
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Abstract
The invention relates to novel methoximinophenylacetamides, to a process for their preparation and to their use as fungicides.
Claims14
A compound of the formula (I),
- in which
- A represents hydrogen, methyl, ethoxycarbonyl, ethyl or cyclopropyl, or has the same meaning as R,
- R represents alkylthio, halogenoalkylthio, alkoxycarbonylthio, having in each case 1 to 4 carbon atoms in the alkyl chains, represents phenylthio which is optionally substituted by halogen, cyano, alkyl, alkoxy or alkoxycarbonyl having in each case 1 to 4 carbon atoms, halogenoalkyl or halogenoalkoxy having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, —S—Y, —S—N(R1R2), where
- R1 represents alkyl having 1 to 4 carbon atoms,
- R2 represents alkyl having 1 to 4 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl moiety, or together with R1 and the nitrogen atom to which they are attached represents an optionally methyl- or ethyl-substituted heterocyclic ring having 5 or 6 ring members,
- Y represents the same grouping which is already linked to the sulphur atom,
- G represents a single bond, represents oxygen, sulphur or represents in each case optionally halogen-, hydroxyl-, C1-C4-alkyl-, C1-C4-halogenoalkyl- or C3-C6-cycloalkyl-substituted alkanediyl, alkenediyl, alkinediyl having in each case up to 4 carbon atoms or one of the groupings below in which in each case the left side is attached to Z:
- —Q—CQ—, —CQ—Q—, —CH2—Q—;
- —Q—CH2—, —CQ—Q—CH2—, —CH2—Q—CQ—, —Q—CQ—CH2—, —Q—CQ—Q—CH2—, —N═N—, —S(O)n—, —CH2—S(O)n—, —CQ—, —S(O)n—CH2—, —C(R8)═N—O—, —C(R8)═N—O—CH2—, —N(R9)—, —CQ—N(R9)—, —N(R9)—CQ—, —Q—CQ—N(R9)—, —N═C(R8)—Q—CH2—, —CH(R8)—O—N═CH—, —C(R8)═N—N═CH—, —N(R9)—CQ—Q—, —CQ—N(R9)—CQ—Q—, —N(R9)—CQ—Q—CH2—, —Q—C(R8)═N—O—CH2—, —N(R9)—C(R8)═N—O—CH2—, —O—CH2—C(R8)═N—O—CH2—, —N═N—C(R8)═N—O—CH2—, —C(═N—O—R10)—C(R8)═N—O—CH2—, —C(═N—O—R10)—C(R8)—O—N═CH—, —C(═N—O—R10)—C(R8)—N—N═CH—, —C(═N—O—R10)—C(R8)—O—N═C(CH3)—, —T—Ar1— or —T—Ar1—Q—, where
- n represents the number 0, 1 or 2,
- Q represents oxygen or sulphur,
- R8 represents hydrogen, cyano, represents in each case optionally halogen-, cyano- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups or represents in each case optionally halogen-, cyano-, carboxyl-, C1-C4-alkyl- or C1-C4-alkoxycarbonyl-substituted cycloalkyl having 3 to 6 carbon atoms, and
- R9 represents hydrogen, hydroxyl, cyano or represents optionally halogen-, cyano- or C1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms or represents optionally halogen-, cyano-, carboxyl-, C1-C4-alkyl- or C1-C4-alkoxycarbonyl-substituted cycloalkyl having 3 to 6 carbon atoms,
- R10 represents hydrogen, C1-C4-alkyl or benzyl which is optionally substituted by halogen, alkyl or alkoxy having in each case 1 to 6 carbon atoms, halogenoalkyl or halogenoalkoxy having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms,
- T represents a single bond, represents oxygen, sulphur, —CH2—O—, —CH2—S— or represents alkanediyl having 1 to 3 carbon atoms,
- Ar1 represents phenylene, naphthylene, cycloalkylene, each of which is optionally mono- or polysubstituted by identical or different substituents or represents heteroarylene or heterocycloalkylene having 3 to 7 ring members, at least one of which represents oxygen, sulphur or nitrogen, and one or two more of which optionally represent nitrogen, where the possible substituents are preferably selected from the list below:
- halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
- in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms;
- in each case straight-chain or branched alkenyl or alkenyloxy having in each case 1 to 6 carbon atoms;
- in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 1 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
- in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and
- cycloalkyl having 3 to 6 carbon atoms and
- L1, L2, L3 and L4 are identical or different and independently of one another each represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or n-, i-propyl, n-, i-, s-, or t-butyl,
- W represents hydrogen, fluorine, cyano or thiocyanato and
- Z represents alkyl having 1 to 8 carbon atoms which is optionally mono- or polysubstituted by identical or different substituents from the list consisting of halogen, cyano, hydroxyl, amino, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl and C1-C4-alkylsulphonyl (which may in each case optionally be substituted by halogen);
- represents in each case optionally halogen-substituted alkenyl or alkynyl having in each case up to 8 carbon atoms;
- tetrahydropyranyl;
- represents cycloalkyl having 3 to 6 carbon atoms which is in each case optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, carboxyl, phenyl (which is optionally substituted
- by halogen, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy or C1-C4-halogenoalkoxy), C1-C4-alkyl and C1-C4-alkoxy-carbonyl;
- represents phenyl, naphthyl, tetrahydrobenzofuranyl, each of which is optionally mono- or polysubstituted by identical or different substituents, or represents heterocyclyl having 3 to 7 ring members, at least one of which represents oxygen, sulphur or nitrogen and one or two more of which optionally represent nitrogen, where the possible substituents are preferably selected from the list below:
- halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;
- in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms;
- in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
- in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, alogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
- t-butyl-substituted tetrazole;
- in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 1 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
- in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl or alkylsulphonyloxy having in each case 1 to 6 carbon atoms in the individual alkyl moieties;
- phenyl;
- in each case doubly attached alkylene or dioxyalkylene having in each case 1 to 6 carbon atoms and being in each case optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
- cycloalkyl having 3 to 6 carbon atoms;
- heterocyclyl or heterocyclyl-methyl having in each case 3 to 7 ring members, 1 to 3 of which are in each case identical or different heteroatoms—in particular nitrogen, oxygen and/or sulphur—or a grouping
- in which
- A1 represents alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
- A2 represents optionally cyano-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted alkyl having 1 to 4 carbon atoms, alkenyl or alkynyl having in each case 2 to 4 carbon atoms.
42 more elements
Dependencies are inferred from the claim text.