Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-09-14
2002-05-07
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S478000, C514S479000
Reexamination Certificate
active
06384067
ABSTRACT:
The present invention relates to novel fungicidal compositions comprising a 2-imidazolin-5-one, 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.
However, it is always desirable to improve the products which can be used by growers in order to combat 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 combat 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 that they will find, among these products, the one which is best suited to the grower's 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 Solanacea diseases.
Another aim of the invention is to propose a novel fungicidal composition which is of improved efficacy against mildew and/or early blight in Solanaceae.
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 sulphur atom;
n is an integer equal to 0 or 1;
Y is a fluorine or chlorine atom or a methyl radical;
and a compound (II) chosen from the group comprising:
compound (IIA) or propamocarb, also known as propyl 3-(dimethylamino)propyl carbamate;
a compound (IIB) of formula (IIB)
in which:
R
1
is a nitrogen atom or the —CH group, and
R
2
is a thiomethyl SCH
3
group or a diethylamino N(C
2
H
5
)
2
group,
the compound (IIC) or cyprodinil, also known as 2-phenylamino-4-cyclopropyl-6-methyl-pyrimidine;
the compound (IID), which is 2-hydroxybenzoic acid or salicylic acid, its esters and its salts, in particular the alkali-metal and alkaline-earth metal salts;
the compound (IIF) or 8-t-butyl-2-(N-ethyl-N-n-propylamino)methyl-1,4-dioxaspiro[4.5]decane, also known as spiroxamine;
the compound (IIG) or isopropyl ester of [2-methyl-1-(1-p-tolylethylcarbomyl)propyl] acid, also known as fencaramide;
the compound (IIH) or 4-chloro-2-cyano-1-dimethylsulphamoyl-5-(4-methylphenyl)imidazole;
the compound (I)/compound (II) ratio being between 0.01 and 50, preferably between 0.1 and 10.
It is clearly understood that the said fungicidal compositions may contain a single compound (II) or more than one such compound, for example 1, 2 or 3 compounds (II) depending on the use for which they are intended.
The composition according to the invention are advantageous for combating, in particular, mildews of the Solanaceae, such as potatoes or tomatoes, as well as for combating mildew and oidium of grapevine.
Compound (I) is known, in particular from patent application EP 629,616.
Compound (IIA), or propamocarb, is a fungicide described in the Pesticide Manual 10th Edition, published by the British Crop Protection Council page 843.
Compound (IIB) and its use are known in particular from European patent applications EP 313,512, EP 420,803 and EP 690,061.
Compound (IIC), or cyprodinil, is described in European patent application EP 310,550.
Compound (IIF) and its use as a fungicide are described in European patent application EP 0,281,842.
Compound (IIG) and its use as a fungicide are described in at least one of the European patent applications EP 0,398,072 or EP 0,472,996.
Compound (IIH) and its use as a fungicide are described in at least one of the European patent applications EP 0,298,196 or EP 0,705,823.
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 below 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 of Solanaceae while at the same time retaining an absence of phytotoxicity towards these crops. This therefore results in an improvement in the spectrum of activity and the 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 the compound (I) is the compound of formula (I) in which M is a sulphur atom and n is equal to 0, also known as (4S)-4-methyl-2-methylthio-4-phenyl-1-phenylamino-2-imidazolin-5-one, are preferred.
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 said 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 is also understood to refer to that defined by application of the Tammes method, “Isoboles, a graphic representation of synergism in pesticides” Netherlands Journal of Plant Pathology, 70 (1964), p. 73-80.
The ranges of the compound (I)/compound (II) ratio indicated above do not in any way limit the scope of the invention, but are rather mentioned as a guide, a person skilled in the art being entirely capable of carrying out complementary tests in order to find other values of the ratio of doses of these 2 compounds for which a synergistic effect is observed.
According to a first preferred variant of the compositions according to the invention, the compound (II) is chosen from the group comprising compounds (IIA), (IIB), (IIC) and (IID). These compositions in particular have advantageous synergistic properties.
According to a more preferred aspect of this first variant of the compositions according to the invention, the compound (II) is compound (IIA) or propamocarb. In this case, particularly improved protection against mildew of Solanaceae is obtained.
In a preferred manner, when the compound (II) is propamocarb, the compound (I)/compound (II) ratio is between 0.01 and 10, preferably between 0.05 and 1 and even more preferably between 0.1 and 1.
According to another more preferred aspect of this first variant of the compositions according to the invention, the compound (II) is compound (IIB).
In this case, the compound of fo
Chazalet Maurice
Latorse Marie-Pascale
Mercer Richard
Aventis CropScience S.A.
Connolly Bove Lodge and Hutz LLP
Robinson Allen J.
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