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US 6,548,549 B1Granted
Acylaminosalicylic acid amides and their uses as pesticides
AssigneeBayer Aktiengesellschaft
InventorsThomas Seitz, Klaus Naumann, Ralf Tiemann, Klaus Stenzel, Gerd Hänssler, Stefan Dutzmann
Life of this patent
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Abstract
The invention relates to known and to new acylaminosalicylamides, to a plurality of processes for their preparation and to their use as pesticides. The present application furthermore relates to new intermediates, to a plurality of processes for their preparation and to their use as pesticides.
Claims9
A compound of the formula (IVa)
- in which
- Z represents a single linkage or an alkylene chain and
- R3 represents in each case optionally mono- to trisubstituted cycloalkyl, cycloalkenyl, aryl or heteroaryl having up to 3 hetero atoms, with the exception of the nitro group as substituent,
- and excluding the compounds
- N-[3-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-nitro-benzamide,
- N-(4-decylphenyl)-2-hydroxy-3-nitro-benzamide,
- N-(3,4-dimethylphenyl)-2-hydroxy-3-nitro-benzamide,
- 3-nitro-N-phenethyl-salicylamide,
- N-benzyl-3-nitro-salicylamide,
- N-(4-aminophenyl)-2-hydroxy-3-nitro-benzamide,
- N-(2-chloro-6-methylphenyl)-2-hydroxy-3-nitro-benzamide,
- N-(3-chloro-2-methylphenyl)-2-hydroxy-3-nitro-benzamide,
- 2-hydroxy-3-nitro-N-(2,4,6-trichlorophenyl)-benzamide,
- N-(2,3-dimethylphenyl)-2-hydroxy-3-nitro-benzamide,
- N-(2-ethylphenyl)-2-hydroxy-3-nitro-benzamide,
- 2-hydroxy-3-nitro-N-phenyl-benzamide,
- 2-hydroxy-N-(4-methylphenyl)-3-nitro-benzamide,
- 2-hydroxy-N-(2-methylphenyl)-3-nitro-benzamide,
- 2-hydroxy-N-(4-methoxyphenyl)-3-nitro-benzamide,
- 2-hydroxy-N-(2-methoxyphenyl)-3-nitro-benzamide,
- 2-hydroxy-N-(2-hydroxyphenyl)-3-nitro-benzamide,
- 2-hydroxy-N-(2-hydroxyphenyl)-3-nitro-benzamide,
- 2-[(2-hydroxy-3-nitrobenzoyl)amino]-benzoic acid,
- N-(2,6-dimethylphenyl)-2-hydroxy-3-nitro-benzamide,
- N-(2,5-dimethylphenyl)-2-hydroxy-3-nitro-benzamide,
- 2-hydroxy-3-nitro-N-[2-phenoxy-5-(trifluoromethyl)phenyl]-benzamide,
- N-[2-chloro-5-(trifluoromethyl)phenyl]-2-hydroxy-3-nitro-benzamide,
- 2-hydroxy-3-nitro-N-[4-(phenylazo)phenyl]-benzamide,
- N-(2,4-dimethylphenyl)-2-hydroxy-3-nitro-benzamide,
- N-(5-chloro-2-methoxyphenyl)-2-hydroxy-3-nitro-benzamide,
- N-(4-chloro-2-methylphenyl)-2-hydroxy-3-nitro-benzamide,
- N-(2-chloro-4-methylphenyl)-2-hydroxy-3-nitro-benzamide,
- N-(4-bromo-2-methylphenyl)-2-hydroxy-3-nitro-benzamide,
- N-(4-chloro-2,5-dimethoxyphenyl)-2-hydroxy-3-nitro-benzamide,
- N-(2,5-dibromophenyl)-2-hydroxy-3-nitro-benzamide,
- N-(2-fluorophenyl)-2-hydroxy-3-nitro-benzamide,
- N-(3-fluorophenyl)-2-hydroxy-3-nitro-benzamide,
- 2-hydroxy-N-(2-iodophenyl)-3-nitro-benzamide,
- 2-hydroxy-N-(3-iodophenyl)-3-nitro-benzamide,
- N-(2-bromophenyl)-2-hydroxy-3-nitro-benzamide,
- N-(3-bromophenyl)-2-hydroxy-3-nitro-benzamide,
- N-(2,5-dichlorophenyl)-2-hydroxy-3-nitro-benzamide,
- N-(3,4-dichlorophenyl)-2-hydroxy-3-nitro-benzamide,
- 2′,3′,5′-trichloro-6′-hydroxy-3-nitro-salicylanilide,
- N-(p-hydroxy-a-methylphenethyl)-3-nitro-salicylamide,
- 3-nitro-3′,5′-bis(trifluoromethoxy)-salicylanilide,
- N-(2,4-dichlorophenyl)-2-hydroxy-3-nitro-benzamide,
- 2-hydroxy-N-(4-iodophenyl)-3-nitro-benzamide,
- N-(4-bromophenyl)-2-hydroxy-3-nitro-benzamide,
- N-(2-chlorophenyl)-2-hydroxy-3-nitro-benzamide,
- N-(3-chlorophenyl)-2-hydroxy-3-nitro-benzamide,
- N-(4-chlorophenyl)-2-hydroxy-3-nitro-benzamide and
- N-(4-fluorophenyl)-2-hydroxy-3-nitro-benzamide.
50 more elements
Compounds of the formula (V):
- in which
- A represents a single linkage or optionally substituted alkylene,
- R2 represents in each case optionally substituted cyloalkyl, cycloalkenyl, aryl or heterocyclyl, with the exception of the nitro group as substituent.
Compounds of the formula (II):
- in which
- A represents a single linkage or an alkylene chain having 1 to 6 carbon atoms,
- R2 represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, tetralinyl, decalinyl, cyclododecatrienyl, indanyl, norbornyl or adamantyl, each of which is optionally monosubstituted to hexasubstituted by fluorine, chlorine, bromine, cyano, carboxyl, methyl, ethyl, methoxy, ethoxy, n- or i-propyl, methoxy-carbonyl or ethoxy-carbonyl;
- or represents in each case optionally monosubstituted to trisubstituted phenyl, naphthyl, benzyl, phenethyl, furyl, benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, quinolyl, pyrimidyl, pyridazinyl, pyrazinyl, oxiranyl, oxetanyl, tetrahydrofuryl, perhydropyranyl, pyrrolidinyl, piperidinyl or morpholinyl, the possible substituents being selected from the enumeration which follows:
- fluorine, chlorine, bromine, cyano, formyl, carbamoyl, thiocarbamoyl, 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, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, acetylamino, formylamino, N-formyl-N-methylamino, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl,
- in each case divalent trimetylene(propane-1,3-diyl), tetramethylene(butane-1,4-diyl), methylenedioxy or ethylenedioxy, each of which is optionally monosubstituted to tetrasubstituled by identical or different substituents from the group consisting of fluorine, chlorine, methyl, trifluoromethyl, ethyl and n- or i-propyl,
- cyclopropyl, cyclobutyl cyclopentyl or cyclohexyl,
- and/or phenyl, phenoxy, phenylthio, benzyl, phenylethyl, phenylpropyl, benzyloxy, benzylthio, phenoxymethyl, phenoxyethyl, phenylthiomethyl or phenylthioethyl, each of which is optionally monosubstituted to tetrasubstituted by identical or different substituents from the group consisting of
- fluorine, chlorine, bromine, cyano, formyl, carbamoyl, thiocarbamoyl, 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, difluorochloromethylthio, trifluorometylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, acetylamino, formylamino, N-formyl-N-methylamino, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy, methoximinomethyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl,
- in each case divalent trimethylene(propane-1,3-diyl), tetramethylene(butane-1,4-diyl), methylenedioxy or ethylenedioxy, each of which is optionally monosubstituted or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, methyl, trifluoromethyl, ethyl and n- or i-propyl, and
- cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
8 more elements
Dependencies are inferred from the claim text.