Selective herbicides based on substituted thien-3-yl-sulfonylamino(thio)carbonyltriazolin(thi)ones and safeners
Abstract
The invention relates to selective herbicidal compositions that comprise an effective amount of an active compound combination comprising (a) one or more compounds of the formula (I) in which Q 1 , Q 2 , R 1 , R 2 , R 3 and R 4 are as defined in the disclosure and salts of the compounds of the formula (I) and (b) at least one of the crop-plant-compatibility-improving compounds listed in the disclosure. The invention further relates to the use of these compositions for controlling undesirable vegetation and to a process for preparing the compositions according to the invention.
Claims
exact text as granted — not AI-modified1 - 9 . (canceled)
10 . A composition comprising an active compound combination comprising
(a) one or more compounds of formula (I) or salts thereof,
in which
Q 1 represents O or S,
Q 2 represents O or S,
R 1 represents optionally cyano-, halogen-, or C 1 -C 4 -alkoxy-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 C 1 -C 4 -alkyl-substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety; represents optionally nitro-, cyano-, halogen-, C 1 -C 4 -alkyl-, or C 1 -C 4 -alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety; or represents optionally nitro-, cyano-, halogen-, C 1 -C 4 -alkyl-, or C 1 -C 4 -alkoxy-substituted heterocyclyl or heterocyclylalkyl having in each case up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and/or 1 or 2 oxygen or sulphur atoms in the heterocyclyl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety,
R 2 represents hydrogen, cyano, nitro, or halogen; represents optionally cyano-, halogen-, or C 1 -C 4 -alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl, or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl group; or represents optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy, or alkynyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkynyl group,
R 3 represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, or iodine, represents optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkyl-carbonyl-, or C 1 -C 4 -alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms; represents optionally fluorine-, chlorine-, and/or bromine- substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms; represents optionally fluorine-, chlorine-, cyano-, C 1 -C 4 -alkoxy-, or C 1 -C 4 -alkoxy-carbonyl-substituted alkoxy, alkylthio, alkylamino, or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl group; represents alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino, or alkynylamino having in each case 3 to 6 carbon atoms in the alkenyl or alkynyl group; represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups; represents optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino, or morpholino; represents optionally fluorine-, chlorine-, bromine-, cyano-, and/or C 1 -C 4 -alkyl-substituted cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio, or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety; or represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C 1 -C 4 -alkyl-, trifluoromethyl-, C 1 -C 4 -alkoxy- and/or C 1 -C 4 -alkoxy-carbonyl-substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino, or arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety,
R 4 represents hydrogen, hydroxyl, amino, or cyano; represents C 2 -C 10 -alkylideneamino; represents optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkyl-carbonyl-, or C 1 -C 4 -alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms; represents optionally fluorine-, chlorine-, and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms; represents optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy-, or C 1 -C 4 -alkoxy-carbonyl-substituted alkoxy, alkylamino, or alkyl-carbonylamino having in each case 1 to 6 carbon atoms in the alkyl group; represents alkenyloxy having 3 to 6 carbon atoms; represents dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups; represents optionally fluorine-, chlorine-, bromine-, cyano-, and/or C 1 -C 4 -alkyl-substituted cycloalkyl, cycloalkylamino, or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety; or represents optionally fluorine-, chlorine-, bromine-, cyano- nitro-, C 1 -C4-alkyl-, trifluoromethyl-, and/or C 1 -C 4 -alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and, where appropriate, 1 to 4 carbon atoms in any alkyl moiety, or
R 3 and R 4 together represent optionally branched alkanediyl having 3 to 6 carbon atoms, and
(b) at least one compound that improves crop plant compatibility selected from the group consisting of the compounds 4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane (AD-67, MON-4660), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-one (dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1-methyl-hexyl 5-chloro-quinolin-8-oxy-acetate (cloquintocet-mexyl), 3-(2-chloro-benzyl)-1-(1-methyl-1-phenyl-ethyl)-urea (cumyluron), α-(cyanomethoximino)-phenylacetonitrile (cyometrinil), 2,4-dichloro-phenoxyacetic acid (2,4-D), 4-(2,4-dichloro-phenoxy)-butyric acid (2,4-DB), 1-(1-methyl-1-phenyl-ethyl)-3-(4-methyl-phenyl)-urea (daimuron, dymron), 3,6-dichloro-2-methoxy-benzoic acid (dicamba), S-1-methyl-1-phenyl-ethyl piperidine-1-thiocarboxylate (dimepiperate), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide (DKA-24), 2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), ethyl 1-(2,4-dichloro-phenyl)-5-trichloro-methyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl—cf. also related compounds in EP-A-174562 and EP-A-346620), phenyl-methyl 2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-α-trifluoro-acetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine (furilazole, MON-13900), ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), 1-(ethoxycarbonyl)-ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor), (4-chloro-o-tolyloxy)-acetic acid (MCPA), 2-(4-chloro-o-tolyloxy)-propionic acid (mecoprop), diethyl 1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro[4.5]decane 4-carbodithioate (MG-838), 1,8-naphthalic anhydride, α-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), 4-(4-chloro-o-tolyl)-butyric acid, 4-(4-chloro-phenoxy)-butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate (MON-7400), ethyl diphenylmethoxyacetate, methyl 1-(2-chloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-(1,1-dimethyl-ethyl)-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 5-(2,4-dichloro-benzyl)-2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5-(4-fluoro-phenyl)-5-phenyl-2-isoxazoline-3-carboxylate, 1,3-dimethyl-but-1-yl 5-chloro-quinolin-8-oxy-acetate, 4-allyloxy-butyl 5-chloro-quinolin-8-oxy-acetate, 1-allyloxy-prop-2-yl 5-chloro-quinolin-8-oxy-acetate, methyl 5-chloro-quinolin-8-oxy-acetate, ethyl 5-chloro-quinolin-8-oxy-acetate, allyl 5-chloro-quinolin-8-oxy-acetate, 2-oxo-prop-1-yl 5-chloro-quinolin-8-oxy-acetate, diethyl 5-chloro-quinolin-8-oxy-malonate, diallyl 5-chloro-quinolin-8-oxy-malonate, diethyl 5-chloro-quinolin-8-oxy-malonate, 4-carboxy-chroman-4-yl-acetic acid (AC-304415), 4-chloro-phenoxyacetic acid, 3,3′-dimethyl-4-methoxy-benzophenone, 1-bromo-4-chloromethylsulphonyl-benzene, 1-[4-(N-2-methoxy-benzoylsulphamoyl)-phenyl]-3-methyl-urea (alias N-(2-methoxy-benzoyl)-4-[(methylamino-carbonyl)-amino]-benzenesulphonamide), 1-[4-(N-2-methoxy-benzoylsulphamoyl)-phenyl]-3,3-dimethyl-urea, 1-[4-(N-4,5-dimethylbenzoyl-sulphamoyl)-phenyl]-3-methyl-urea, 1-[4-(N-naphthylsulphamoyl)-phenyl]-3,3-dimethyl-urea, N-(2-methoxy-5-methyl-benzoyl)-4-(cyclopropylamino-carbonyl)-benzenesulphonamide,
and
a compound of formula (IIa)
where, for each of formulas (IIa), (IIb), or (IIc),
n represents a number between 0 and 5,
A 1 represents one of the divalent heterocyclic groups
A 2 represents optionally C 1 -C 4 -alkyl- and/or C 1 -C 4 -alkoxy-carbonyl-substituted alkanediyl having 1 or 2 carbon atoms,
R 5 represents hydroxyl, mercapto, amino, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, or di-(C 1 -C 4 -alkyl)-amino,
R 6 represents hydroxyl, mercapto or amino; or optionally C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 2 -C 4 -alkenoxy-substituted C 1 -C 6 -alkoxy, C 2 -C 6 -alkenoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, or di-(C 1 -C 4 -alkyl)-amino,
R 7 represents optionally fluorine-, chlorine-, and/or bromine-substituted C 1 -C 4 -alkyl,
R 8 represents hydrogen; optionally fluorine-, chlorine-, and/or bromine-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, or C 2 -C 6 -alkynyl; C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl-C 1 -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, or piperidinyl; or optionally fluorine-, chlorine-, and/or bromine-, or C 1 -C 4 -alkyl-substituted phenyl,
R 9 represents hydrogen; optionally fluorine-, chlorine-, and/or bromine-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, or C 2 -C 6 -alkynyl; C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl-C 1 -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, or piperidinyl, or optionally fluorine-, chlorine-, and/or bromine-, or C 1 -C 4 -alkyl-substituted phenyl; or R 9 together with R 8 represents C 3 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl, each of which is optionally substituted by C 1 -C 4 -alkyl, phenyl, furyl, a fused-on benzene ring, or by two substituents that together with the C atom to which they are attached form a 5- or 6-membered carbocycle,
R 10 represents hydrogen, cyano, or halogen; or represents optionally fluorine, chlorine-, and/or bromine-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, or phenyl,
R 11 represents hydrogen; or optionally hydroxyl-, cyano-, halogen-, or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, or tri-(C 1 -C 4 -alkyl)-silyl,
R 12 represents hydrogen, cyano, or halogen; or represents optionally fluorine-, chlorine-, and/or bromine-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, or phenyl,
X 1 represents nitro, cyano, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy,
X 2 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy,
X 3 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy,
and a compound of formula (IId) formula (IIe) where, for each of formulas (IId) or (IIe),
n represents a number between 0 and 5,
R 13 represents hydrogen or C 1 -C 4 -alkyl,
R 14 represents hydrogen or C 1 -C 4 -alkyl,
R 15 represents hydrogen; optionally cyano-, halogen-, or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di-(C 1 -C 4 -alkyl)-amino; or optionally cyano-, halogen-, or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkylthio, or C 3 -C 6 -cycloalkylamino,
R 16 represents hydrogen; optionally cyano-, hydroxyl-, halogen-, or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl; optionally cyano- or halogen-substituted C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl; or optionally cyano-, halogen-, or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl,
R 17 represents hydrogen; optionally cyano-, hydroxyl-, halogen-, or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl; optionally cyano- or halogen-substituted C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl; optionally cyano-, halogen-, or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl; or optionally nitro-, cyano-, halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -halogenoalkyl-, C 1 -C 4 -alkoxy-, or C 1 -C 4 -halogenoalkoxy-substituted phenyl; or R 17 together with R 16 represents optionally C 1 -C 4 -alkyl-substituted C 2 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl,
X 4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy, and
X 5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy.
11 . A composition according to claim 10 wherein
Q 1 represents O or S, Q 2 represents O or S, R 1 represents optionally cyano-, fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s-, or t-butyl; represents optionally cyano-, fluorine-, or chlorine-substituted propenyl, butenyl, propynyl, or butynyl; represents optionally cyano-, fluorine-, chlorine-, methyl-, or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, or cyclohexylmethyl; represents optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, or trifluoromethoxy-substituted phenyl, phenylmethyl, or phenylethyl; or represents optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, or n- or i-propoxy-substituted heterocyclyl or heterocyclyl-methyl, where each heterocyclyl group is selected from the group consisting of oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, and tetrahydrothienyl, R 2 represents hydrogen, cyano, fluorine, chlorine, or bromine; represents optionally cyano-, fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, or ethylsulphonyl; or represents optionally cyano-, fluorine-, or chlorine-substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, or butynyloxy, R 3 represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, or bromine; represents optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl, methoxycarbonyl-, ethoxycarbonyl-, or n- or i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s-, or t-butyl; represents optionally fluorine-, chlorine-, and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl, or butynyl; represents optionally fluorine-, chlorine-, cyano-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, or n- or i-propoxycarbonyl-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s-, or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s-, or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-, or t-butylamino, acetylamino, or propionylamino; represents propenyloxy, butenyloxy, ethynyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio, butynylthio, propenylamino, butenylamino, propynylamino, or butynylamino; represents dimethylamino, diethylamino, or dipropylamino; represents optionally fluorine-, chlorine-, methyl-, and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino, or cyclohexylmethylamino; or represents optionally fluorine-, chlorine-, bromine-, methyl-, trifluoromethyl-, methoxy-, or methoxy-carbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino, or benzylamino, and R 4 represents hydrogen, hydroxyl, or amino; represents optionally fluorine-, chlorine-, cyano-, methoxy-, or ethoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s-, or t-butyl; represents optionally fluorine, chlorine, and/or bromine-substituted ethenyl, propenyl, butenyl, propynyl, or butynyl; represents optionally fluorine-, chlorine-, cyano-, methoxy-, or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s-, or t-butoxy, methylamino, ethylamino, n- or i-propylamino, or n-, i-, s-, or t-butylamino; represents propenyloxy or butenyloxy; represents dimethylamino or diethylamino; represents optionally fluorine-, chlorine-, methyl-, and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, or cyclohexylmethyl; or represents optionally fluorine-, chlorine-, methyl-, trifluoromethyl-, and/or methoxy-substituted phenyl or benzyl, or R 3 and R 4 together represent trimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl), or pentamethylene (pentane-1,5-diyl).
12 . A composition according to claim 10 wherein
Q 1 represents O, Q 2 represents O, R 1 represents optionally fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, or n- or i-propyl, R 2 represents fluorine, chlorine, or bromine; or represents optionally fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, or n- or i-propyl, R 3 represents hydrogen, chlorine, or bromine; represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, or n- or i-propyl; represents optionally fluorine- or chlorine-substituted ethenyl, propenyl, butenyl, propynyl, or butynyl; represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, or n- or i-propylamino; represents propenyloxy, propynyloxy, propenylthio, propynylthio, propenylamino, or propynylamino; represents dimethylamino or diethylamino; represents optionally fluorine-, chlorine-, or methyl-substituted cyclopropyl, cyclopropyloxy, cyclopropylmethyl, or cyclopropylmethoxy, and R 4 represents optionally fluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, or n- or i-propyl; represents optionally fluorine- or chlorine-substituted ethenyl, propenyl, or propynyl; represents optionally fluorine-, chlorine-, methoxy-, or ethoxy-substituted methoxy, ethoxy, or n- or i-propoxy; represents methylamino; or represents cyclopropyl.
13 . A composition according to claim 10 wherein
n represents the numbers 0, 1, 2, 3, or 4, A 2 represents optionally methyl-, ethyl-, methoxycarbonyl-, or ethoxycarbonyl-substituted methylene or ethylene, R 5 represents hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s-, or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s-, or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-, or t-butylamino, dimethylamino, or diethylamino, R 6 represents hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s-, or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s-, or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-, or t-butylamino, dimethylamino, or diethylamino, R 7 represents optionally fluorine-, chlorine-, and/or bromine-substituted methyl, ethyl, or n- or i-propyl, R 8 represents hydrogen; optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, propenyl, butenyl, propynyl, butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl; or optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, or n-, i-, s-, or t-butyl-substituted phenyl, R 9 represents hydrogen; optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, propenyl, butenyl, propynyl, butynyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl; or optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, or n-, i-, s-, or t-butyl-substituted phenyl; or R 9 together with R 8 represents one of the radicals —CH 2 —O—CH 2 -CH 2 — or —CH 2 -CH 2 —O—CH 2 -CH 2 —, which are optionally substituted by methyl, ethyl, furyl, phenyl, a fused benzene ring, or by two substituents that together with the C atom to which they are attached form a 5- or 6-membered carbocycle, R 10 represents hydrogen, cyano, fluorine, chlorine, or bromine; or represents optionally fluorine-, chlorine-, and/or bromine-substituted methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or phenyl, R 11 represents hydrogen; or optionally hydroxyl-, cyano-, fluorine-, chlorine, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s-, or t-butyl, R 12 represents hydrogen, cyano, fluorine, chlorine, or bromine; or represents optionally fluorine-, chlorine-, and/or bromine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or phenyl, X 1 represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, or trifluoromethoxy, X 2 represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, or trifluoromethoxy, X 3 represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, or trifluoromethoxy, R 13 represents hydrogen, methyl, ethyl, or n- or i-propyl, R 14 represents hydrogen, methyl, ethyl, or n- or i-propyl, R 15 represents hydrogen; optionally cyano-, fluorine-, chlorine-, methoxy- ethoxy-, or n- or i-propoxy-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, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-, or t-butylamino, dimethylamino, or diethylamino; or optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, or n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, or cyclohexylamino, R 16 represents hydrogen; optionally cyano-, hydroxyl-, fluorine- chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, or s-butyl; optionally cyano-, fluorine-, chlorine-, or bromine-substituted propenyl, butenyl, propynyl, or butynyl; or optionally cyano-, fluorine-, chlorine-, bromine-, methyl- ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, R 17 represents hydrogen; optionally cyano-, hydroxyl-, fluorine- chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, or s-butyl; optionally cyano-, fluorine-, chlorine-, or bromine-substituted propenyl, butenyl, propynyl, or butynyl; or optionally cyano-, fluorine-, chlorine-, bromine-, methyl- ethyl-, or n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl; or 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-, or trifluoromethoxy-substituted phenyl; or R 17 together with R 16 represents in each case optionally methyl- or ethyl-substituted butane-1,4-diyl (trimethylene), pentane-1,5-diyl, 1-oxabutane-1,4-diyl, or 3-oxapentane-1,5-diyl, X 4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, or trifluoromethoxy, and X 5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, or trifluoromethoxy.
14 . A composition according to claim 10 wherein the crop-plant-compatibility-improving compound is one or more compounds selected from the group consisting of the active compounds AD-67, cloquintocet-mexyl, dichlormid, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, MON-7400, flurazole, furilazole, fenchlorim, cumyluron, dymron, a compound of formula (IId)
in which R 13 and R 14 each represent hydrogen, R 15 represents methoxymethyl, (X 4 ) n represents 2-methoxy, and (X 5 ) n represents hydrogen, and
a compound of formula (IIe)
in which R 13 and R 16 each represent hydrogen, R 17 represents cyclopropyl, (X 4 ) n represents the group 2-methoxy or the two groups 2-methoxy and 5-methyl, and (X 5 ) n represents hydrogen.
15 . A composition according to claim 10 comprising an active compound combination comprising
(a) a compound of formula (I) or a salt thereof,
in which Q 1 and Q 2 each represent oxygen, R 1 , R 2 , and R 4 each represent methyl, and R 3 represents methoxy, and
(b) a crop-plant-compatibility-improving compound of formula (IIe) in which R 13 and R 16 each represent hydrogen, R 17 represents cyclopropyl, (X 4 ) n represents 2-methoxy, and (X 5 ) n represents hydrogen.
16 . A method for controlling undesirable plants comprising allowing an effective amount of a composition according to claim 10 to act on undesirable plants and/or their habitat.
17 . A process for preparing a herbicidal composition comprising mixing a composition according to claim 10 with one or more surfactants and/or extenders.Join the waitlist — get patent alerts
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