Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-05-18
2004-06-22
Padmanabhan, Sreeni (Department: 1617)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S391000, C514S479000
Reexamination Certificate
active
06753339
ABSTRACT:
The present invention relates to novel fungicidal compositions comprising a 2-imidazolin-5-one derivative and an amino acid amide derivative, which are intended in particular for protecting crops. The invention also relates to a process for protecting crops against fungal diseases.
Compounds derived from 2-imidazolin-5-ones with fungicidal action are known, in particular from European patent application EP 551,048, these compounds making it possible to prevent the growth and development of phytopathogenic fungi which attack or are liable to attack crops.
International patent application WO 96/03044 also discloses a certain number of fungicidal compositions comprising a 2-imidazolin-5-one in combination with one or more fungicidal active materials.
Patent applications EP-A-0,775,696 and EP-A-0,472,966 present novel compounds for fungicidal use which have an amino acid amide structure.
However, it is always desirable to improve the products which can be used by growers in order to control fungal diseases of crops, and in particular mildews.
It is also always desirable to reduce the doses of chemical products spread into the environment to control fungal attacks on crops, in particular by reducing the application doses of the products.
Lastly, it is always desirable to increase the number of antifungal products available to growers in order for them to find, among these products, the one which is best suited to their specific use.
One aim of the invention is thus to provide a novel fungicidal composition which is useful for the problems outlined above.
Another aim of the invention is to propose a novel fungicidal composition which is useful in the preventive and curative treatment of fungal diseases, for example of Solanacea plants and of grapevine.
Another aim of the invention is to propose a novel fungicidal composition which is of improved efficacy against mildew and/or Septoria leaf blotch in Solanacea plants and grapevine.
Another aim of the invention is to propose a novel fungicidal composition which is of improved efficacy against mildew and/or oidium and/or botrytis in grapevine.
It has now been found that these aims may be achieved, partly or totally, by means of the fungicidal compositions according to the present invention.
The subject of the present invention is thus, firstly, fungicidal compositions comprising a compound (I) of formula:
in which:
M represents an oxygen or sulfur atom;
n is an integer equal to 0 or 1;
Y is a fluorine or chlorine atom or a methyl radical;
and a compound of formula (II):
in which:
R and R′, which ate identical or different, are chosen, independently of each other, from a linear or branched alkyl radical containing from 1 to 6 carbon atoms,
A represents a group chosen from A1 and A2 which have the respective formulae:
X represents the hydrogen atom, a halogen atom chosen from chlorine, fluorine, bromine and iodine, a linear or branched alkyl radical containing from 1 to 6 carbon atoms, or a linear or branched alkoxy radical containing from 1 to 6 carbon atoms, and
the asterisks represent asymmetric centers;
the compound (I)/compound (II) ratio being between 50 and 0.01, preferably between 10 and 0.01 and even more preferably between 5 and 0.5.
The preferred compounds of formula (II) for the fungicidal compositions according to the invention are such that the asymmetric carbon center of the amino acid gives it the L configuration.
It is clearly understood that all the possible configurations of compound (II), i.e. all the isomers formed by the various configurations of the two asymmetric carbons, are included in the field of the present invention.
It is clearly understood that said fungicidal compositions can include a single compound (I) or more than one such compound and/or a single compound (II) or ore than one such compound, as well as another fungicidal compound, depending on the use for which they are intended.
The compositions according to the invention are advantageous for controlling, in particular, mildew and Septoria leaf blotch in crops, such as cucumber or pea, for example, in Solanacea plants, such as potato or tomato, as well as for controlling mildew in grapevine.
The compositions according to the invention can also be used for controlling other phytopathogenic diseases of crops which are well known to The person skilled in the art who has at his or her disposal the compounds of formula (I) and of formula (II).
Compound (I) is known, in particular, from patent application EP-A-0,629,616.
Compound (II), when A represents the group A1, and its use as a fungicide are described in particular in European patent application EP-A-0,775,696.
Compound (II), when A represents the group A2, and its use as a fungicide are described in particular in European patent application EP-A-0,472,996.
The compound (I)/compound (II) ratio is defined as being the ratio of the weight of these 2 compounds. This is likewise the case for any ratio of 2 chemical compounds, mentioned hereinbelow in the present text, insofar as a definition different from this ratio is not expressly indicated.
These compositions generally appreciably improve the respective and isolated action of compound (I) and of compound (II) for a certain number of fungi that are particularly harmful in crops, in particular for Solanaceae, more particularly for mildew in Solanacea plants, while at the same time retaining an absence of phytotoxicity toward these crops. This therefore results in an improvement in the spectrum of activity and a possibility of decreasing the respective dose of each active material used, the latter quality being particularly advantageous for readily appreciated ecological reasons.
The fungicidal compositions according to the invention for which:
compound (I) is the compound of formula (I) in which M is a sulfur atom and n is equal to 0, also known as (4-S)-4-methyl-2-methylthio-4-phenyl-1-phenylamino-2-imidazolin-5-one, referred to hereinbelow as “Compound A”, and
compound (IIA) is the compound of formula (II) in which R represents the isopropyl radical, A represents the group (A1), X represents the fluorine atom placed in position 6 on the 2-benzothiazolyl radical, the amino acid has the L configuration and the asymmetric carbon borne by the 2-benzothiazolyl radical, the R configuration, also known as N
1
-[(R)-1-(6-fluoro-2-benzothiazolyl)ethyl]-N
2
-isopropoxycarbonyl-L-valinamide, referred to hereinbelow as “Compound B”, or alternatively
compound (IIB) is the compound of formula (II) in which R represents the isopropyl radical, A represents the group (A2), X represents the methyl radical placed in position 4 on the phenyl radical, whether it is in the form of a racemate or mixtures of enantiomers and/or of diastereoisomers or in the form of a pure optical isomer, also known as isopropyl [2-methyl-1-(1-phenylethylcarbamoyl)-propyl]carbamate, referred to hereinbelow as “Compound C”, are preferred.
A particularly advantageous form of compound (C) is the product commonly called Iprovalicarb.
In the compositions according to the invention, the compound (I)/compound (II) ratio is advantageously chosen so as to produce a synergistic effect. The term synergistic effect is understood to refer in particular to that defined by Colby S. R. in an article entitled “Calculation of the synergistic and antagonistic responses of herbicide combinations” published in the journal Weeds, 1967, 15, p. 20-22. The latter article uses the formula:
E=X+Y−XY
/100
in which E represents the expected percentage of inhibition of the disease for the combination of the two fungicides at defined doses (for example equal to x and y respectively), X is the percentage of inhibition observed for the disease by the compound (I) at a defined dose (equal to x), Y is the percentage of inhibition observed for the disease by the compound (II) at a defined dose (equal to y). When the percentage of inhibition observed for the combination is greater than E, there is a synergistic effect.
The term “synergistic effect” also means the effect defined by
Chazalet Maurice
Duvert Patrice
Gouot Jean-Marie
Mercer Richard
Aventis Cropscience SA
Hui San-ming
Padmanabhan Sreeni
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