초록

The invention relates to novel substituted aryl ketones of the formula (I) in which Z, X, R and n are as defined in the disclosure, to processes for their preparation and to their use as crop treatment agents, and to intermediates for preparing compounds of the formula (I).

대표청구항 ▼

What is claimed is: 1. A herbicidal compound of formula (I), in which n represents the number 0, 1, or 2, R represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, or arylalkyl, X represent hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, or halo;

What is claimed is: 1. A herbicidal compound of formula (I), in which n represents the number 0, 1, or 2, R represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, or arylalkyl, X represent hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, or halo; or represents optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, or dialkylaminosulphonyl, and Z represents one of the groups where m represents the number 0 to 6, R1 represents hydrogen or halogen; or represents optionally substituted alkyl, alkylthio or aryl, with the proviso that if m represents the numbers 2 to 6, then R1 together with a second radical R1 optionally also represents oxygen or alkandiyl (alkylene), R2 represents hydroxyl, formyloxy, or halogen; represents optionally substituted alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy, alkynyloxy, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylcarbonyloxy, arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy, arylalkylthio, arylalkylsulphinyl, or arylalkylsulphonyl; or represents heterocyclyl that is attached via nitrogen, R3 represents cycloalkyl, R4 represents hydrogen; or represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, or arylalkyl, and R5 represents hydroxyl or formyloxy; or represents optionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy, alkynyloxy, arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy, or arylsulphonyloxy. 2. A compound of formula (I) according to claim 1 in which n represents the number 0 or 2, R represents optionally cyano-, halogen-, C1-C 4-alkoxy-, C1-C4-alkylthio-, C1-C 4-alkylsulphinyl-, or C1-C4-alkylsulphonyl-substituted alkyl having 1 to 6 carbon atoms; represents optionally cyano-or halogen-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms; represents optionally cyano-, halogen-, or C1-C 4-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety; or represents optionally nitro-, cyano-, halogen-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy-, or C1-C4-haloalkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, X represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, or halogen; or represents optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C 1-C4-alkylsulphinyl-, or C1-C4-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, m represents the number 0, 1, 2, or 3, R1 represents hydrogen or halogen; represents optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-, or C 1-C4-alkylsulphonyl-substituted alkyl or alkylthio having in each case 1 to 6 carbon atoms; or represents phenyl, with the proviso that if m represents 2 or 3, then R1 together with a second radical R1 optionally also represents oxygen or alkanediyl (alkylene) having 3 to 5 carbon atoms, R2 represents hydroxyl, formyloxy, or halogen; represents optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkoxy-carbonyl-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-, or C1-C 4-alkylsulphonyl-substituted alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, or alkylsulphonyloxy having in each case 1 to 6 carbon atoms; represents optionally halogen-substituted alkenyloxy or alkynyloxy having in each case 3 to 6 carbon atoms; represents optionally nitro-, cyano-, halogen-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C4-alkoxy-, C1-C 4-haloalkoxy-, C1-C4-alkylthio-, C1-C 4-haloalkylthio-, C1-C4-alkylsulphinyl-, C 1-C4-haloalkylsulphinyl-, C1-C4-alkylsulphonyl-, or C1-C4-haloalkylsulphonyl-substituted aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylcarbonyloxy, arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy, arylalkylthio, arylalkylsulphinyl, or arylalkylsulphonyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety; or represents pyrrolyl, pyrazolyl, imidazolyl, triazolyl, or tetrazolyl, each of which is attached via nitrogen, R3 represents optionally cyano-, halogen-, or C 1-C4-alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, R4 represents hydrogen; represents optionally cyano-halogen-, C1-C4-alkoxy-, C1-C4-alkyl-thio-, C1-C4-alkylsulphinyl-, or C1-C4-alkylsulphonyl-substituted alkyl having 1 to 6 carbon atoms; represents optionally cyano-or halogen-substituted alkenyl or alkynyl having in each case 3 to 6 carbon atoms; represents optionally cyano-, halogen-, or C1-C4-alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety; or represents optionally nitro-, cyano-, halogen-, C1-C4-alkyl-, C 1-C4-haloalkyl-, C1-C4-alkoxy-, C 1-C4-haloalkoxy-, C1-C4-alkylthio-, C 1-C4-haloalkylthio-, C1-C4-alkylsulphinyl-, C1-C4-haloalkylsulphinyl-, C1-C4-alkylsulphonyl-, or C1-C4-haloalkylsulphonyl-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, and R5 represents hydroxyl or formyloxy; represents optionally cyano-, halogen-, or C1-C4-alkoxy-substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, or alkylsulphonyloxy having in each case 1 to 6 carbon atoms in the alkyl groups; represents optionally cyano-or halogen-substituted alkenyloxy or alkynyloxy having in each case 3 to 6 carbon atoms; or represents optionally nitro-, cyano-, halogen-, C1-C4-alkyl-, C1-C4-haloalkyl-, C1-C 4-alkoxy-, C1-C4-haloalkoxy-, C1-C 4-alkylthio-, C1-C4-haloalkylthio-, C1-C4-alkylsulphinyl-, C1-C4-haloalkylsulphinyl-, C1-C4-alkylsulphonyl-, or C1-C4-haloalkylsulphonyl-substituted arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy, or arylsulphonyloxy having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety. 3. A compound of formula (I) according to claim 1 in which n represents the number 2, R represents optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-, methylthio-, ethylthio-, n-or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n-or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-and/or n-or i-propylsulphonyl-substituted methyl, ethyl, n-or i-propyl, n-, i-, s-, or t-butyl, or n-, i-, s-, or t-pentyl; represents optionally cyano-, fluorine-, chlorine-, and/or bromine-substituted ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl, or pentynyl; represents optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, and/or n-or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, or cyclohexylmethyl; or represents optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, n-, i-, s-, or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n-or i-propoxy-, difluoromethoxy-, and/or trifluoromethoxy-substituted phenyl, naphthyl, phenylmethyl, phenylethyl, or phenylpropyl, X represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or iodine; or represents optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, or ethylsulphonyl-substituted methyl, ethyl, n-or i-propyl, n-, i-, s-, or t-butyl, methoxy, ethoxy, n-or i-propoxy, n-, i-, s-, or t-butoxy, methylthio, ethylthio, n-or i-propylthio, n-, i-, s-, or t-butylthio, methylsulphinyl, ethylsulphinyl, n-or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n-or i-propylsulphonyl, methylamino, ethylamino, n-or i-propylamino, n-, i-, s-or t-butylamino, dimethylamino, diethylamino, dimethylaminosulphonyl, or diethylaminosulphonyl, m represents the number 0, 1, or 2, R1 represents hydrogen, fluorine, chlorine, or bromine; represents optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-, methylthio-, ethylthio-, n-or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, or ethylsulphonyl-substituted methyl, ethyl, n-or i-propyl, n-, i-, s-, or t-butyl, methylthio, ethylthio, n-or i-propylthio, or n-, i-, s-, or t-butylthio; or represents phenyl, with the proviso that if m represents 2, then R 1 together with a second radical R1 optionally also represents oxygen, propane-1,3-diyl, or butane-1,4-diyl, R2 represents hydroxyl, formyloxy, fluorine, or chlorine; represents optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, n-or i-propoxycarbonyl-, methylthio-, ethylthio-, n-or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, or ethylsulphonyl-substituted methoxy, ethoxy, n-or i-propoxy, methylthio, ethylthio, n-or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, acetyloxy, propionyloxy, n-or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n-or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-or i-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, or n-or i-propylsulphonyloxy; represents optionally fluorine-, chlorine-, and/or bromine-substituted propenyloxy, butenyloxy, propynyloxy, or butynyloxy; represents optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, n-, i-, s-, or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n-or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n-or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, or trifluoromethylsulphonyl-substituted phenyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl, phenylcarbonyloxy, phenylcarbonylmethoxy, phenylsulphonyloxy, phenylmethoxy, phenylmethylthio, phenylmethylsulphinyl, or phenylmethylsulphonyl; or represents pyrazolyl, imidazolyl, or triazolyl, each of which is attached via nitrogen, R3 represents optionally cyano-, fluorine-, chlorine-, methyl-, or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, R4 represents hydrogen; represents optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-, methylthio-, ethylthio-, n-or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, or ethylsulphonyl-substituted methyl, ethyl, n-or i-propyl, or n-, i-, s-, or t-butyl; represents optionally cyano-, fluorine-, chlorine-, and/or bromine-substituted propenyl, butenyl, propynyl, or butynyl; represents optionally cyano-, fluorine-, chlorine-, methyl-, or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, or cyclohexylmethyl; or represents optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, n-, i-, s-, or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n-or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n-or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, or trifluoromethylsulphonyl-substituted phenyl or phenylmethyl, and R5 represents hydroxyl or formyloxy; represents optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-substituted methoxy, ethoxy, n-or i-propoxy, acetyloxy, propionyloxy, n-or i-butyroyloxy, methoxy-carbonyloxy, ethoxycarbonyloxy, n-or i-propoxycarbonyloxy, methyl-aminocarbonyloxy, ethylaminocarbonyloxy, n-or i-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, or n-or i-propylsulphonyloxy; represents optionally cyano-, fluorine-, chlorine-, and/or bromine-substituted propenyloxy, butenyloxy, propynyloxy, or butynyloxy; or represents optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, n-, i-, s-, or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n-or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n-or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, or trifluoro-methylsulphonyl-substituted phenylmethoxy, phenylcarbonyloxy, phenylcarbonylmethoxy, or phenylsulphonyloxy. 4. A compound of formula (I) according to claim 1 in which R represents optionally fluorine-and/or chlorine-substituted methyl, ethyl, n-or i-propyl, or n-, i-, or s-butyl; represents optionally fluorine-, chlorine-, or methyl-substituted cyclopropyl, cyclopentyl, or cyclohexyl; or represents optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n-or i-propoxy-, difluoromethoxy-, or trifluoromethoxy-substituted phenyl or phenylmethyl, X represents nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or iodine; or represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, and/or ethylsulphonyl-substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, dimethylamino, or dimethylaminosulphonyl, m represents the number 0, R1 represents hydrogen; represents optionally fluorine-or chlorine-substituted methyl, ethyl, n-or i-propyl, methylthio, ethylthio, or n-or i-propylthio; or represents phenyl, with the proviso that if m represents 2, then R1 together with a second radical R1 optionally also represents oxygen, propane-1,3-diyl, or butane-1,4-diyl, R2 represents hydroxyl; represents optionally fluorine-or chlorine-substituted methoxy, ethoxy, n-or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n-or i-propoxycarbonyl, methylthio, ethylthio, n-or i-propylthio, acetyloxy, propionyloxy, n-or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n-or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-or i-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, or n-or i-propylsulphonyloxy; represents optionally fluorine-, chlorine-, and/or bromine-substituted propenyloxy, butenyloxy, propynyloxy, or butynyloxy; represents optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n-or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n-or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, or trifluoromethylsulphonyl-substituted phenyloxy, phenylthio, phenylcarbonyloxy, phenylcarbonylmethoxy, phenylsulphonyloxy, phenylmethoxy, or phenylmethylthio; or represents pyrazolyl or imidazolyl, each of which is attached via nitrogen, R3 represents optionally fluorine-, chlorine-, or methyl-substituted cyclopropyl, R4 represents hydrogen; represents optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-, methylthio-, ethylthio-, n-or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, or ethylsulphonyl-substituted methyl, ethyl, n-or i-propyl, or n-, i-, s-, or t-butyl; represents optionally fluorine-, chlorine-, and/or bromine-substituted propenyl, butenyl, propynyl, or butynyl; represents optionally fluorine-, chlorine-, or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, or cyclohexylmethyl; or represents optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n-or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n-or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, or trifluoromethylsulphonyl-substituted phenyl or phenylmethyl, and R5 represents hydroxyl; represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-substituted methoxy, ethoxy, n-or i-propoxy, acetyloxy, propionyloxy, n-or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n-or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-or i-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, or n-or i-propylsulphonyloxy; represents optionally fluorine-, chlorine-, and/or bromine-substituted propenyloxy, butenyloxy, propynyloxy, or butynyloxy; or represents optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n-or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n-or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, or trifluoromethylsulphonyl-substituted phenylmethoxy, phenylcarbonyloxy, phenylcarbonylmethoxy, or phenylsulphonyloxy. 5. A composition comprising one or more compounds of formula (I) according to claim 1 and one or more extenders and/or surfactants. 6. A method for controlling unwanted plants comprising allowing one or more compounds of formula (I) according to claim 1 to act on unwanted plants and/or their habitat. 7. A method for controlling unwanted plants comprising allowing a composition according to claim 5 to act on unwanted plants and/or their habitat.