Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai
Reexamination Certificate
1999-11-29
2002-09-10
Low, Christopher S. F. (Department: 1653)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Peptide containing doai
C526S243000, C562S567000
Reexamination Certificate
active
06448228
ABSTRACT:
FIELD OF THE INVENTION
The present relates to new dipeptide compounds capable of controlling phytopathogens which cause considerable economic damage to agricultural crops.
More specifically, the present invention relates to new dipeptide compounds capable of effectively controlling phytopathogens of crops of great economic interest, such as, for example, vines, potatoes and tobacco, as well as their agronomic use, alone or mixed with one or more active principles with a fungicidal activity, and the process for their preparation.
DESCRIPTION OF THE RELATED ART
The patent application EP 652 229 A2 discloses suitably functionalized oligopeptide compounds having a high fungicidal activity consisting of one or two aliphatic amino acids, such as valine, leucine and isoleucine, conjugated to one or two aromatic amino acids, such as phenyl-glycine, phenylalanine and &bgr;-phenylalanine (or 3-amino-3-phenylpropanoic acid), whose free amine and carboxyl functions can also be suitably functionalized.
Patent application EP 718 280 A2 again describes compounds based on 3-amino-3-arylpropanoic acids suitably substituted. Among the compounds based on 3-amino-3-arylpropanoic acids claimed, there are also dipeptide compounds obtained by means of bonds between the amine group of said 3-amino-3-arylpropanoic acids and the carboxyl group of an amino acid, such as valine appropriately functionalized on its amine function.
Said patent applications EP 652 229 A2 and EP 718 280 A2, among the numerous examples which illustrate the invention, describe dipeptlde compounds, whose basic skeleton consists of L-valine conjugated by means of its carboxyl group with an aromatic &bgr;-amino acid (3-amino-3-aryl-propanoic acid) and whose structures can be defined by a single general formula (Ia):
wherein:
R
1
represents a linear or branched C
1
-C
8
alkyl group, or a phenyl group;
R
2
represents a linear or branched C
1
-C
8
alkyl group;
R
3
can be a phenyl group optionally substituted.
On the basis of what is described in the above patent applications, these dipeptide compounds are particularly effective in the control of Oomycetes.
The products specified which can be defined by this general formula are generally characterized by the functionalization of the amine residue with a carboxy-tertbutyl group (R
1
therefore means tert-butyl) or by the esterification of the carboxyl residue with an alkyl group, and the R
2
group therefore has the meaning of a methyl, ethyl and isopropyl group, in the presence of an R
3
phenyl group.
The compounds having general formula Ia also allow synergic fungicidal mixtures to be obtained with the levorotatory isomer of methyl (N-phenylacetyl-N-2,6-xylyl)alaninate (Benalaxyl), as described in the patent WO 98 26654 A2.
BRIEF SUMMARY OF THE INVENTION
The Applicant has now found that new dipeptide compounds having formula (I), which have never been described before, have a higher fungicidal activity than those of the dipeptide compounds specified in the known art.
DETAILED DESCRIPTION OF THE INVENTION
The present invention therefore relates to dipeptide compounds having formula (I):
wherein:
R
1
represents an isopropyl or phenyl group;
R
2
represents a methyl group;
R
3
can be a phenyl group substituted in position 4 with an R
4
group; or it can represent a 2-benzothiazole group, optionally substituted with an R
5
group;
R
4
and R
5
can be a fluorine or chlorine atom; a methyl or ethyl group; or a methoxyl group; or they can represent a cyano group.
The configuration of the atom of the valine residue present in all compounds having formula (I) is S, according to the Cahn, Ingold and Prelog convention.
The absolute configuration of the chiral atom of aromatic &bgr;-amino acid incorporated in the dipeptide compound may, on the contrary, be either S or R.
The compounds of the present invention, considering jointly the asymmetrical centres present in the molecule, may be in diastereoisomeric forms S—S or S—R, wherein the first letter refers to the chiral centre of valine whereas the second letter describes the chiral centre of aromatic &bgr;-amino acid, or they can be present as a diastereoisomeric mixture in which the two forms are in any molar ratio.
The Applicant has found that compounds in which the absolute configuration of the chiral atom of aromatic &bgr;-amino acid incorporated in the dipeptide compound is R, have a greater fungicidal activity.
A particular aspect of the present invention therefore relates to dipeptide compounds having formula (I) wherein the absolute configuration of the chiral atom of the &bgr;-amino acid residue is R, as represented by general formula (II)
wherein:
R
1
, R
2
, R
3
have the meaning defined above (formula I).
The compounds of the present invention can be conveniently used in agriculture as a diastereoisomeric mixture in which the two forms can be present in any molar ratio.
According to present conventions, a compound having formula (I) with an epimeric form S—RS contains these diastereoisomeric forms S—S and S—R in an equimolecular ratio.
Owing to the higher activity of compounds in which the absolute configuration of the chiral atom of aromatic &bgr;-amino acid is R, the compounds having formula (I) are preferably used as a diastereoisomeric mixture in which the diastereoisomeric form S—R is greater than 80%.
Even more preferable are diastereoisomeric mixtures in which the diastereoisomeric form S—R is present in greater quantities, such as, for example, diastereoisomeric mixtures containing the form S—R in quantities exceeding 90%, 95% or 98%.
The use of compounds having formula (I) in the sole dlastereoisomeric form S—R, is the most preferable.
The compounds having formula (I) can be used alone or optionally associated with at least one other compound having a fungicidal activity.
The present invention therefore relates to fungicidal compositions comprising:
a) a dipeptide compound having formula (I) as a diastereoisomeric mixture in which the two forms can be present in any molar ratio, or as a sole diasatereoisomeric form S—R;
b) one or more fungicides selected from:
(1) Cymoxanil corresponding to 1-(2-cyano-2-methoxyimino-acetyl)-3-ethylurea;
(2) Fosetyl-Al corresponding to the aluminum salt of ethyl hydrogen phosphonate;
(3) Potassium phosphonate;
(4) Benalaxyl corresponding to methyl N-(phenyl-acetyl)-N-2,6-xylyl-RS-alaninate;
(5) Methyl N-(phenylacetyl)-N-2,6-xylyl-R-alaninate;
(6) Metalaxyl corresponding to methyl N-(2-methoxyacetyl)-N-2,6-xylyl-RS-alaninate;
(7) Mefenoxam corresponding to methyl N-(2-methoxyacetyl-N-2,6-xylyl-R-alaninate;
(8) Oxadixyl corresponding to 2-methoxy-N-(2-oxo-1,3-oxazolidin-3-yl)acet-2′,6′-xylidinide;
(9) Ofurace corresponding to DL-3-[N-chloroacetyl-N-(2,6-xylyl)-amino]-&ggr;-butyrolactone;
(10) Iprovalicarb corresponding to O-(1-methylethyl)-N-[2-methyl-1-[[[1-(4-methylphenyl)ethyl]-amino]carbonyl]propyl]carbamate;
(11) Azoxystrobin corresponding to methyl (E)-2-[2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate;
(12) Kresoxym-methyl corresponding to methyl (E)-methoxyimino-&agr;-[o-tolyloxy)-o-tolyl]acetate;
(13) Metominofen corresponding to the experimental abbreviation SSF-126 and corresponding to N-methyl-(E)-methoxyimino-(2-phenoxyphenyl)acetamide;
(14) Acylbenzolar corresponding to methylbenzothiadiazole-7-thiocarboxylate;
(15) Famoxadone corresponding to 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)oxazolidin-2,4-dione;
(16) Fenamidone corresponding to 4-methyl-4-phenyl-1-(phenylamino)-2-methylthioimidazolidin-5-one;
(17) IKF916 corresponding to 2-cyano-4-chloro-5-(4-methylphenyl)-1-(N,N-dimethylaminosulfamoyl)-imidazole;
(18) Fluazinam corresponding to 3-chloro-N-(3-chloro-5-trlfluoromethyl-2-pyridyl)-&agr;,&agr;,&agr;-tri-fluoro-2,6-dinitro-p-toluidine;
(19) Dimethomorph corresponding to (E,Z)-4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloyl]morpholine;
(20) Flumetover corresponding to N,N-diethylamide of 4-trifluoromethyl-6-(3,4-dimethoxyphenyl)benzoic a
Colombo Laura
Filippini Lucio
Gusmeroli Marilena
Mirenna Luigi
Mormile Silvia
Isagro Ricerca S.r.l.
Low Christopher S. F.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
LandOfFree
Dipeptide compounds having a high fungicidal activity and... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Dipeptide compounds having a high fungicidal activity and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Dipeptide compounds having a high fungicidal activity and... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2833790