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US 8,148,419 B2Granted
N-(1-alkyl-2-phenylethyl)-carboxamide derivatives and use thereof as fungicides
AssigneeBayer CropScience AG
InventorsPierre-Yves Coqueron, Darren James Mansfield, Philippe Desbordes, Heiko Rieck, Pierre Genix, Alain Villier, Marie-Claire Grosjean-Cournoyer
Life of this patent
Estimating the term…
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.
Claims19
A compound of formula (I)
- in which:
- n is 1, 2, 3, 4 or 5;
- each X is independently selected from the group consisting of 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-alkylsulfenyl, a C1-C8-halogenoalkylsulfenyl having 1 to 5 halogen atoms, a C1-C8-alkylsulfinyl, a C1-C8-halogenoalkylsulfinyl having 1 to 5 halogen atoms, a C1-C8-alkylsulfonyl, a C1-C8-halogenoalkylsulfonyl 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, and a phenylamino;
- R1, R2, R3 and R4 are independently selected from the group consisting of a hydrogen atom, a C1-C6-alkyl, and a C1-C6-alkyl-C3-C7-cycloalkyl;
- provided that at least one of R1, R2, R3 and R4 is different from hydrogen;
- R5 is selected from the group consisting of a hydrogen atom, a C1-C6-alkyl, and a C3-C7-cycloalkyl;
- Ya is selected from the group consisting of a halogen atom, a cyano group, a sulfanyl group, a pentafluoro-λ6-sulfanyl group, a formyl 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-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 C1-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, and a C3-C8-halogenocycloalkyl having 1 to 5 halogen atoms;
- and
- Y1, Y2, and Y3 are independently selected from the group consist of a hydrogen atom, a halogen atom, a C1-C6-alkyl;
- a C1-C6-halogenoalkyl, an amino group, a cyano group, a C1-C4-alkylamino and a di-(C1-C4-alkyl)amino;
- as well as any salt, N-oxide, or optically active isomer thereof.
8 more elements
A process for the preparation of a compound of formula (I),
- which comprises reacting a 1-alkyl-2-phenylethylamine derivative of general formula (II) or one of its salts
- in which
- n is 1, 2, 3, 4 or 5;
- each X is independently selected from the group consisting of 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-C8alkynyl, 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-C8alkylcarbonylamino, a C1-C8-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a C1-C8-alkylaminocarbonyloxy, a di-C1-C8-alkylaminocarbonyloxy, a C1-C8-alkyloxycarbonyloxy, C1-C8-alkylsulfenyl, a C1-C8-halogenoalkylsulfenyl having 1 to 5 halogen atoms, a C1-C8-alkylsulfinyl, a C1-C8-halogenoalkylsulfinyl having 1 to 5 halogen atoms, a C1-C8-alkylsulfonyl, a C1-C8-halogenoalkylsulfonyl 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, and a phenylamino,
- R1, R2, R3 and R4 are independently selected from the group consisting of a hydrogen atom, a C1-C6-alkyl, and a C1-C6-alkyl-C3-C7-cycloalkyl;
- provided that at least one of R1, R2, R3 and R4 is different from hydrogen;
- and
- R5 is selected from the group consisting of a hydrogen atom, a C1-C6-alkyl, and a C3-C7-cycloalkyl;
- with a carboxylic acid derivative of the formula (III)
- in which:
- Het is a 5-, 6- or 7-membered heterocycle comprising one, two or three heteroatoms which may be the same or different;
- Het being linked by a carbon atom;
- Ya is an ortho-substituent and is selected from the group consisting of halogen atom, a cyano group, a sulfanyl group, a pentafluoro-λ6-sulfanyl group, a formyl 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-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 C1-C8-alkynyloxy, a C1-C8-halogenoalkynyloxy having 1 to 5 halogen atoms, a C3-C8-cycloalkyl, and a C3-C8-halogenocycloalkyl having 1 to 5 halogen atoms,
- each Y is independently selected from the group consisting of a hydrogen atom, a halogen atom, a C1-C6-alkyl, a C1-C6-halogenoalkyl, an amino group, a cyano group, a C1-C4-alkylamino, and a di-(C1-C4-alkyl)amino;
- p is 1, 2, 3, 4 or 5;
- and
- L1 is a leaving group selected from the group consisting of
- (A) a halogen atom, a hydroxyl group, —OR77, and —OCOR77, wherein R77 is selected from the group consisting of a C1-C6 alkyl, a C1-C6 haloalkyl, a benzyl, 4-methoxybenzyl, and pentafluorophenyl, and
- (B) a group of the formula
- in the presence of a catalyst and, if L1 is a hydroxyl group, in the presence of a condensing agent.
17 more elements
A compound of the formula
- wherein:
- X1, X2, X3, X4, and X5 are independently selected from the group consisting of hydrogen and halogen, provided that at least one of X1, X2, X3, X4, and X5 is halogen;
- R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen and C1-C6 alkyl, provided that at least one of R1, R2, R3, and R4 is C1-C6 alkyl;
- R5 is selected from the group consisting of hydrogen, C1-C6 alkyl, and C3-C7 cycloalkyl;
- Ya is selected from the group consisting of a halogen atom, a cyano group, a C1-C4-alkyl, and a C1-C4-halogenoalkyl having 1 to 5 halogen atoms;
- Y1 and Y3 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a C1-C4-alkyl, and a C1-C4-halogenoalkyl having 1 to 5 halogen atoms;
- and
- Y2 is selected from the group consisting of a hydrogen atom, a cyano group, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms.
5 more elements
Dependencies are inferred from the claim text.