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US 2009/0156682 A1Published application
N-(1-Methyl-2Phenylethyl)Benzamide Derivatives
AssigneeBayer CropScience AG
InventorsDarren Mansfield, Pierre-Yves Coqueron, Heiko Rieck, Philippe Desbordes, Alain Villier, Marie-Claire Grosjean-Cournoyer, Pierre Genix
Life of this patent
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Abstract
A compound of general formula (I): A process for preparing this compound. A fungicidal composition comprising a compound of general formula (I). A method for treating plants by applying a compound of general formula (I) or a composition comprising it.
Claims12
A compound derivative of general formula (I)
- in which:
- n is 1, 2, 3, 4 or 5;
- p is 1,2, 3 or 4;
- X is the same or different and is a halogen atom, a nitro group, a cyano group, an amino group, a sulfanyl group, a pentafluoro-λ6-sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C1-C6-alkyl group, a C1-C8-alkyl, a C1-C8-halogenoalkyl having 1 to 5 halogen atoms, a C2-C8-alkenyl, a C2-C8-alkynyl, a C1-C8-alkylamino, a di-C1-C8-alkylamino, a C1-C8-alkoxy, a C1-C8-halogenoalkoxy having 1 to 5 halogen atoms, a C1-C8-alkylsulfanyl, a C1-C8-halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C2-C8-alkenyloxy, a C2-C8-halogenoalkenyloxy having 1 to 5 halogen atoms, a C3-C8-alkynyloxy, a C3-C8-halogenoalkynyloxy having 1 to 5 halogen atoms, a C3-C8-cycloalkyl, a C3-C8-halogenocycloalkyl having 1 to 5 halogen atoms, a C1-C8-alkylcarbonyl, a C1-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C1-C8-alkylcarbamoyl, a di-C1-C8-alkylcarbamoyl, a N—C1-C8-alkyloxycarbamoyl, a C1-C8-alkoxycarbamoyl, a N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl, a C1-C8-alkoxycarbonyl, a C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C1-C8-alkylcarbonyloxy, a C1-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C1-C8-alkylcarbonylamino, a C1-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C1-C8-alkylaminocarbonyloxy, a di-C1-C8-alkylaminocarbonyloxy, a C1-C8-alkyloxycarbonyloxy, a C1-C8-alkylsulphenyl, a C1-C8-halogenoalkylsulphenyl having 1 to 5 halogen atoms, a C1-C8-alkylsulphinyl, a C1-C8-halogenoalkylsulphinyl having 1 to 5 halogen atoms, a C1-C8-alkylsulphonyl, a C1-C8-halogenoalkylsulphonyl having 1 to 5 halogen atoms, a (C1-C6-alkoxyimino)-C1-C6-alkyl, a (C1-C6-alkenyloxyimino)-C1-C6-alkyl, a (C1-C6-alkynyloxyimino)-C1-C6-alkyl, a (benzyloxyimino)-C1-C6-alkyl, a benzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanyl or a phenylamino;
- R1 and R2 are the same or different and are a hydrogen atom, a C1-C6-alkyl or a C1-C6-alkyl-C3-C7-cycloalkyl;
- R3 and R4 are the same or different and are a hydrogen atom, a C1-C6-alkyl or a C1-C6-alkyl-C3-C7-cycloalkyl;
- R5 is a hydrogen atom, a C1-C6-alkyl or a C3-C7-cycloalkyl;
- Y is the same or different and is a hydrogen atom, a halogen atom, a C1-C6-alkyl or a C1-C6-halogenoalkyl;
- and
- Ya is a halogen atom, a C1-C6-alkyl or a C1-C6-halogenoalkyl;
- as well as its salts, N-oxydes, metallic complexes, metalloidic complexes and optically active isomers;
- with the proviso that compound of general formula (I) is different from:
- 2,3,4,5,6-pentafluoro-N-[2-(2,5-dimethoxyphenyl)-1-methylethyl]-benzamide;
- 2,3,4,5,6-pentafluoro-N-[2-(4-methoxyphenyl)-1-methylethyl]-benzamide;
- 2,3,4,5,6-pentafluoro-N-[1-methyl-2-(3,4,5-trimethoxyphenyl)ethyl]-benzamide;
- 2,3,4,5,6-pentafluoro-N-[1-(phenylmethyl)ethyl-2,2,2-d3]-benzamide;
- 2,3,4,5,6-pentafluoro-N-[2-(4-methoxyphenyl)-1-methylethyl]-N-methyl-benzamide;
- 2,3,4,5,6-pentafluoro-N-[2-(2-methoxyphenyl)-1-methylethyl]-N-methyl-benzamide;
- 2,3,4,5,6-pentafluoro-N-[2-(4-chlorophenyl)-1-methylethyl]-benzamide;
- 2-chloro-N-[2-(3-chloro-4-methoxyphenyl)ethyl]-benzamide;
- N-[2-(2-bromophenyl)ethyl]-2-iodobenzamide;
- 2-bromo-N-[2-(3,4-dimethoxyphenyl)ethyl]-benzamide;
- 2,4-dichloro-N-[1-methyl-2-(3-trifluoromethylphenyl)ethyl]-benzamide;
- 2-chloro-N-[2-(3,4-dimethoxyphenyl)ethyl]-benzamide;
- 2-chloro-N-[2-(4-chlorophenyl)-1-methyl-ethyl]-benzamide;
- N-[2-(3-chloro-4-methoxyphenyl)ethyl]-2-methylbenzamide;
- N-[2-(3,4-dimethoxyphenyl)ethyl]-2-methylbenzamide;
- 2-(2-chloroethyl)-N-[2-(4-methoxyphenyl)ethyl]-benzamide;
- and
- N-[2-(3-chloro-4-methoxyphenyl)ethyl]-2,6-dimethylbenzamide.
27 more elements
A process for the preparation of compound of general formula (I), which comprises a 1-alkyl-2phenylethylamine derivative of general formula (II) or one of its salt
- n is 1, 2, 3, 4 or 5;
- X is the same or different and is a halogen atom, a nitro group, a cyano group, an amino group, a sulfanyl group, a pentafluoro-λ6-sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C1-C6-alkyl group, a C1-C8-alkyl, a C1-C8-halogenoalkyl having 1 to 5 halogen atoms, a C7-C8-alkenyl, a C2-C8-alkynyl, a C1-C8-alkylamino, a di-C1-C8-alkylamino, a C1-C8-alkoxy, a C1-C8-halogenoalkoxy having 1 to 5 halogen atoms, a C1-C8-alkylsulfanyl, a C1-C8 halogenoalkylsulfanyl having 1 to 5 halogen atoms, a C7-C8-alkenyloxy, a C2-C8-halogenoalkenyloxy having 1 to 5 halogen atoms, a C3-C8-alkynyloxy, a C3-C8-halogenoalkynyloxy having 1 to 5 halogen atoms, a C3-C8-cycloalkyl, a C3-C8-halogenocycloalkyl having 1 to 5 halogen atoms, a C1-C8-alkylcarbonyl, a C1-C8-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a C1-C8-alkylcarbamoyl, a di-C1-C8-alkylcarbamoyl, a N—C1-C8-alkyloxycarbamoyl a C1-C8-alkoxycarbamoyl, a N—C1-C8-alkyl-C1-C8-alkoxycarbamoyl, a C1-C8-alkoxycarbonyl, a C1-C8-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a C1-C8-alkylcarbonyloxy, a C1-C8-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a C1-C8-alkylcarbonylamino, a C1-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C1-C8-alkylaminocarbonyloxy, a di-C1-C8-alkylaminocarbonyloxy, a C1-C8-alkyloxycarbonyloxy, a C1-C8-alkylsulphenyl, a C1-C8-halogenoalkylsulphenyl having 1 to 5 halogen atoms, a C1-C8-alkylsulphinyl, a C1-C8-halogenoalkylsulphinyl having 1 to 5 halogen atoms, a C1-C8-alkylsulphonyl, a C1-C8-halogenoalkylsulphonyl having 1 to 5 halogen atoms, a (C1-C6-alkoxyimino)-C1-C6-alkyl, a (C1-C6-alkenyloxyimino)-C1-C6-alkyl, a (C1-C6-alkynyloxyimino-C1-C6-alkyl, a (benzyloxyimino)-C1-C6-alkyl, a benzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanyl or a phenylamino;
- R1 and R2 are the same or different and are a hydrogen atom, a C1-C6-alkyl or a C1-C6-alkyl-C3-C7-cycloalkyl;
- R3 and R4 are the same or different and are a hydrogen atom, a C1-C6-alkyl or a C1-C6-alkyl-C1-C7-cycloalkyl;
- and
- R5 is a hydrogen atom, a C1-C6-alkyl or a C3-C7-cycloalkyl;
- with a carboxylic acid derivative of the general formula (III)
- in which:
- p is 1, 2, 3 or 4;
- Y is the same or different and is a hydrogen atom, a halogen atom, a C1-C6-alkyl or a C1-C6-halogenoalkyl;
- Ya is a halogen atom a C1-C6-alkyl or a C1-C6-halogenoalkyl;
- and
- L1 is a leaving group chosen as being a halogen atom, a hydroxyl group, —OR6, —OCOR6, R6 being a C1-C6 alkyl, a C1-C6 haloalkyl, a benzyl, 4-methoxybenzyl, pentafluorophenyl or a group of formula:
- in the presence of a catalyst and, if L1 is a hydroxyl group, in the presence of a condensing agent.
11 more elements
Dependencies are inferred from the claim text.