Title of Invention | "A COMPOUND OF GENERAL FORMULA (I)" |
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Abstract | A compound of general formula (I) |
Full Text | The present invention relates to a compound of general formula (I). The present invention relates to novel N-[2-(2-pyridinyl)ethyl]carboxamides derivatives, their process of preparation, their use as fungicides, particularly in the form of fungicidal compositions, and methods for the control of phytopathogenic fungi of plants using these compounds or their compositions. The international patent application WO 01/11965 discloses a broad family of fungicidal compounds in which the 2-pyridyl group is substituted by at least one halogenoalkyl group. It is always of high-interest in the agriculture field to use novel pesticidal compounds in order to avoid or to fight the development of resistant strains to the active ingredients used by the farmer. We have now found a new family of compounds which possess the above mentioned characteristics. Accordingly, the present invention relates to N-[2-(2-pyridinyI)ethyl]carboxamide derivative of general formula (I) : (Formula Removed) in which: -n is 1, 2, 3 or 4; - X is the same or different and is a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a sulfanyl group, a pentafluoro-X -sulfanyl group, a formyl group, a formyloxy group, a formylamino group, a carboxy group, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a (hydroxyimino)-C1-C6-alkyl group, a C1-C8-alkyl, 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-haiogenoalkynyloxy 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-alkylcarbamoyi, a di-C1-C8-alkylcarbamoyl, a N-C1-C8-alkyloxycarbamoyl, a C1-C8-alkoxycarbamoyl, a N-C1-C8-alkyl-C1-C8- We Claim: 1. A compound of general formula (I) (Formula Removed) in which: -n is 1,2, 3 or 4; - X is the same or different and is a halogen atom, a C1-C8-alkyl, a C1-C6-alkoxyimino, a (C1-C6-alkoxyimino)-C1-C6-alkyl, or a C1-C6-alkoxy-C1-C6-alkylcarbonyl; - R1 and R2 are the same or different and are chosen, independently of each other, as being a hydrogen atom, a halogen atom, a cyan group, a hydroxy group, a C1-C6-alkyl, a C1-C6-halogenoalkyl having 1 to 5 halogen atoms, a C2-C6-alkenyl, a C1-C6-alkoxy, a C1-C6-alkylsulfanyl, a C1-C6-alkylsulfenyl, a C1-C6-alkylsulfmyl, a C1-C6-alkoxycarbonyl, a C1-C6-alkylcarbonylamino, a C1-C6-alkoxycarbonyloxy, a C1-C6-alkoxycarbonylamino or a phenyl group, or R1 and R2 may form together a cyclopropyl, a cylcobutyl, a cyclopentyl or a cyclohexyl; - R3 and R4 are the same or different and are chosen, independently of each other, as being a hydrogen atom, a halogen atom, a cyano group, a C1-C6 alkyl, a C1-C6- halogenoalkyl having 1 to 5 halogen atoms or a phenyl group; with the proviso that when three of the four substituents R1, R2, R3 and R4 are a hydrogen atom, then the fourth substituent is not a hydrogen atom; - R5 is a hydrogen atom, a cyan group, a forrnyl group, a hydroxy group, a C1-C6-alkyl, a C1-C6-halogenoalkyl having 1 to 5 halogen atoms, a C1-C6-alkoxy, a C1-C6- halogenoalkoxy having 1 to 5 halogen atoms, a C3-C6-cycloalkyl, a C3-C6- halogenocycloalkyl having 1 to 5 halogen atoms, a C2-C6-alkenyl, a C2-C6-alkynyl, a C1-C6-alkoxy- C1-C6-alkyl, a C1-C6-cyanoalkyl, a C1-C6-aminoalkyl, a C1-C6- alkylamino-C1-C6-alkyl, a di-C1-C6,-alkylamino-C1-C6-alkyl, a C1-C6-alkylcarbonyl, a C1-C6-halogenalkylcarbonyl having 1 to 5 halogen atoms, a C1-C6-alkyloxycarbonyl, a C1-C6-benzyloxycarbonyl, a C1-C6-alkoxy- C1-C6-alkylcarbonyl, a C1-C6-alkylsulfonyl or a C1-C6-halogenoalkylsulfonyl having 1 to 5 halogen atoms; Het represents: * (Het-4); (Formula Removed) in which : - R14 and R15 may be the same or different and may be a hydrogen atom, a halogen atom, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atones, a C1-C4-alkylthio, a C1-C4-alkylsulphonyl, a phenyl optionally substituted by a halogen atom or a C1-C4-alkyl or a pyridyl optionally substituted by a halogen atom or a C1-C4-alkyl; and - R16 may be a halogen atom, a cyano group, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms or a C1-C4-halogenoalkoxy having 1 to 5 halogen atoms; * (Het-5) (Formula Removed) in which : - R17 and R18 may be the same or different and may be a hydrogen atom, a halogen atom, a C1-C4-alkyl, a C1-C4-alkyloxy or a C1-C4-halogenoalkyl having 1 to 5 halogen atoms; and - R19 may be a hydrogen atom, a halogen atom, a C1-C4-alkyl or a C1-C4-halogenoalkyl having 1 to 5 halogen atoms; provided that the R18 and R19 are not both a hydrogen atom; * (Het-10) (Formula Removed) in which : - R32 may be a hydrogen atom, a halogen atom, an amino group, a cyano group, a C1-C4-alkylamino, a di-(C1-C4-alkyl)amino, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms or a phenyl optionally substituted by a halogen atom or a C1-C4-alkyl; and - R33 may be a halogen atom, a C1-C4-alkyl or a C1-C4-halogeuoxlkyl having 1 to 5 halogen atoms; *(Het-ll) (Formula Removed) in which: - R34 may be a hydrogen atom, a halogen atom, an amino group, a cyano group, a C1-C4-alkylamino, a di-(C1-C4-alkyl)amino, a C1-C4-alkyl or a C1-C4-halogenoalkyl having 1 to 5 halogen atoms; and - R35 may be a halogen atom, a C1-C4-alkyl or a C1-C4-halogenoalkyl having 1 to 5 halogen atoms; * (Het-12) (Formula Removed) in which : - R36 may be a halogen atom, a cyano group, a nitro group, a C1-C4-alkyl, a C1-C4- halogenoalkyl having 1 to 5 halogen atoms, a C3-C6-cycloalkyl, a C1-C4-alkoxy, a C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, a C1-C4-alkylthio, a C1-C4- halogenoalkylthio having 1 to 5 halogen atoms, an aminocarbonyl group or an amincarbonyl-C1 -C4-alkyl; - R37 may be a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1-C4-alkyl, a C1-C4-alkoxy or a C1-C4-alkylthio; and - R38 may be a hydrogen atom, a phenyl, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms, a hydroxy-C1-C4-alkyl, a C2-C6-alkenyl, a C3-C6-cyclo-alkyl; a C1-C4-alkylthio-C1-C4-alkyl, a C1-C4-halogenoalkylthio-C1-C4-alkyl having 1 to 5 halogen atoms, a C1-C4-alkoxy-C1-C4-alkyl or a C1-C4-halogenoalkoxy-C1-C4-alkyl having 1 to 5 halogen atoms; * (Het-13) (Formula Removed) in which: - R39 may be a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms, a C3-C6-cycloalkyl, a C1-C4-alkoxy, a C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, a C1-C4-alkylthio, a C1-C4-halogenoalkylthio having 1 to 5 halogen atoms, an aminocarbonyl or an aminocarbonyl-C1-C4-alkyl; - R40 may be a hydrogen atom, a halogen atom, a cyano group, a C1-C4-alkyl, a C1-C4-alkoxy, a C1-C4-halogenoalkoxy having 1 to 5 halogen atoms or a C1-C4-alkylthio; and - R41 may be a hydrogen atom, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms, a hydroxy-C1-C4-alkyl, a C2-C6-alkenyl, a C3-C6-cycloalkyl, a C1-C4-alkylthio-C1-C4-alkyl, a C1-C4-halogenoalkylthio-C1-C4-alkyl having 1 to 5 halogen atoms, a C1-C4-alkoxy-C1-C4-alkyl, a C1-C4-halogenoalkoxy-C1-C4-alkyl having 1 to 5 halogen atoms or a phenyl optionally substituted by a halogen atom, a C1-C4-alkyl, a C1-C4-alkoxyalkyl or a nitro group; provided that the R39 and R40 are not both a hydrogen atom; * (Het-14) (Formula Removed) in which: - R42 may be a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms, a C3-C6-cycloalkyl, a C1-C4-alkoxy, a C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, a C1-C4-alkylthio, a C1-C4-halogenoalkylthio having 1 to 5 halogen atoms, an aminocarbonyl, or an aminocarbonyl-C1-C4-alkyl; - R43 may be a hydrogen atom, a halogen atom, a cyano group, a C1-C4-alkyl, a C1-C4-alkoxy, a C1-C4-alkylthio or a C1-C4-halogenoalky having 1 to 5 halogen atoms; - R44 may be a hydrogen atom, a phenyl, a benzyl, a C1-C4-alkyl, a C1-C4-halogenoalkyl having 1 to 5 halogen atoms, a hydroxy-C1-C4-alkyl, a C2-C6-alkenyl, a C3-C6-cycloalkyl, a C1-C4-alkylthio-C1-C4-alkyl, a C1-C4-halogenoalkylthio-C1-C4-alkyl having 1 to 5 halogen atoms, a C1-C4-alkoxy-C1-C4-alkyl, a C1-C4-halogenoalkoxy-C1-C4-alkyl having 1 to 5 halogen atoms; provided that R43 and R44 are not both a hydrogen atom; Het being at least substituted in ortho position; as well as its salts, N-oxydes, metallic and metalloidic complexes. 2. A compound as claimed in claim 1, wherein n is 1, 2 or 3. 3. A compound as claimed in any of the claims 1 to 2, wherein the 2-pyridyl is substituted in 3-, 5- and/or in 6-position. 4. A compound as claimed in any of the claims 1 to 3, wherein R1 and R2 are chosen, independently of each other, as being a halogen atom, a C1-C6-alkyl, a C1-C6-halogenoalkyl having 1 to 5 halogen atoms or a C1-C6-alkylcarbonylamino. 5. A compound as claimed in claim 4, wherein R3 and R4 are chosen, independently of each other, as being a halogen atom, a C1-C6-alkyl, a C1-C6-halogenoalkyl having 1 to 5 halogen atoms or a phenyl group. 6. A compound as claimed in any of the claims 1 to 5, wherein R5 is a hydrogen atom or a C3-C7-cycloalkyl. 7. A process for the preparation of a compound of general formula (I) as defined as claimed in any of the claims 1 to 6, which comprises reacting a 2-pyridine derivative of general formula (II) or one of its salt: (Formula Removed) in which X, n, R1, R2, R3, R4 and R5 are as in any of the preceding claims; with a carboxylic acid derivative of the general formula (III) (Formula Removed) in which: - Het is as defined in any of the preceding claims ; and - L2 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 (Formula Removed) in the presence of a catalyst and, if L2 is a hydroxyl group, in the presence of a condensing agent of the kind such as wherein described. 8. A fungicidal composition comprising an effective amount of a compound as claimed in any of the claims 1 to 6 and an agriculturally acceptable support wherein the composition may contain from 0.05 to 99% (by weight) of active material. |
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4094-DELNP-2006--Claims-(21-03-2012).pdf
4094-DELNP-2006-Abstract-(11-11-2011).pdf
4094-DELNP-2006-Assignment-(10-09-2010).pdf
4094-DELNP-2006-Claims-(11-11-2011).pdf
4094-DELNP-2006-Corresponcence-Others-(16-05-2011).pdf
4094-DELNP-2006-Correspondence Others-(11-11-2011).pdf
4094-DELNP-2006-Correspondence Others-(15-11-2011).pdf
4094-DELNP-2006-Correspondence Others-(16-11-2011).pdf
4094-delnp-2006-Correspondence Others-(17-08-2012).pdf
4094-delnp-2006-Correspondence Others-(21-03-2012).pdf
4094-DELNP-2006-Correspondence Others-(30-08-2011).pdf
4094-delnp-2006-correspondence-others 1.pdf
4094-DELNP-2006-Correspondence-Others-(10-09-2010).pdf
4094-delnp-2006-correspondence-others.pdf
4094-DELNP-2006-Description (Complete)-(11-11-2011).pdf
4094-delnp-2006-description (complete).pdf
4094-DELNP-2006-Form-1-(11-11-2011).pdf
4094-DELNP-2006-Form-1-(21-03-2012).pdf
4094-DELNP-2006-Form-2-(11-11-2011).pdf
4094-DELNP-2006-Form-2-(21-03-2012).pdf
4094-DELNP-2006-Form-3-(11-11-2011).pdf
4094-DELNP-2006-Form-3-(15-11-2011).pdf
4094-DELNP-2006-Form-3-(16-05-2011).pdf
4094-delnp-2006-Form-3-(17-08-2012).pdf
4094-DELNP-2006-Form-3-(21-03-2012).pdf
4094-DELNP-2006-Form-3-(30-08-2011).pdf
4094-DELNP-2006-Form-5-(21-03-2012).pdf
4094-DELNP-2006-GPA-(10-09-2010).pdf
4094-DELNP-2006-GPA-(11-11-2011).pdf
4094-DELNP-2006-Petition-137-(11-11-2011).pdf
Patent Number | 253803 | ||||||||||||||||||||||||
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Indian Patent Application Number | 4094/DELNP/2006 | ||||||||||||||||||||||||
PG Journal Number | 35/2012 | ||||||||||||||||||||||||
Publication Date | 31-Aug-2012 | ||||||||||||||||||||||||
Grant Date | 27-Aug-2012 | ||||||||||||||||||||||||
Date of Filing | 17-Jul-2006 | ||||||||||||||||||||||||
Name of Patentee | BAYER CROPSCIENCE AG., | ||||||||||||||||||||||||
Applicant Address | ALFRED NOBEL STRASSE 50, D-40789 MONHEIM, GERMANY | ||||||||||||||||||||||||
Inventors:
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PCT International Classification Number | C07D 409/12 | ||||||||||||||||||||||||
PCT International Application Number | PCT/EP2005/003282 | ||||||||||||||||||||||||
PCT International Filing date | 2005-03-01 | ||||||||||||||||||||||||
PCT Conventions:
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