IT9020454A1 - ANTIFUNGAL MIXTURES - Google Patents

Description

Description of the industrial invention entitled: "ANTIFUNGINE MIXTURES"

Summary Antifungal mixtures containing the compound:

and at least one covering fungicide selected from: ethylene bis (dithiocarbamate) of manganese and zinc; manganese ethylene bis (dithiocarbamate); zinc ethylene bis (dithiocarbamate); zinc dimethylthiocarbamate; copper (I) oxide.

The present invention refers to a cyanoacetamide derivative having improved antifungal activity in the agricultural field, used in mixture with so-called covering products.

The present invention also relates to antifungal compositions containing the cyanoacetamide derivative and at least one covering product, hereinafter defined.

The cyanoacetamide derivative responds to the following formula (I):

Published European patent application No. 250744 describes the use of antifungal products, with the same application spectrum, having the general formula:

in which, among other meanings:

n = 2;

A = alkylene

X = 0;

R1 = polyfluoroalkyl e

R = alkyl

however compound (I) is not specifically prepared and characterized.

On the other hand, it is known that fungicidal agents in general, including those having the above formula in a special way, to be conveniently used in agriculture are mixed with defined covering products, such as dithiocarbamates, for example Mancozeb, or with metal salts. such as copper salts, for example copper oxychloride, to increase the spectrum, control the emergence of resistant strains and guarantee a protracted protective action over time.

In the course of further research on the products described in the cited European patent application, we verified that, by mixing these compounds with covering products, their activity surprisingly declined, while only the product of formula (I) kept its good activity substantially unaltered, in some cases improving it, in the presence of said covering compounds.

Therefore, the object of the present invention is to provide a cyanoacetamide derivative which demonstrates improved antifungal activity in the presence of the commonly used covering substances.

Another object is to provide the relative compositions comprising the derivative of formula (I) and at least one covering compound, hereinafter defined, in addition to the usual formulation components.

Finally, a further object is to provide a method for combating fungal infections in useful plants with the use of the above compositions.

These, and other purposes, are achieved, according to the present invention, by the cyanoacetamide product of formula (I) indicated above in a mixture with covering fungicides, selected from:

Ethylene bis (dithiocarbamate) of manganese and zinc (Mancozeb); Ethylene bis (dithiocarbamate) of manganese (Maneb); Ethylene bis (dithiocarbamate) of zinc (Zineb);

Zinc dimethylthiocarbamate (Ziram);

Copper (I) Oxide (Copper Oxidule) and related compositions that contain them.

The designations in parentheses are the trade names of the corresponding chemical compounds.

The compositions object of the invention essentially consist of the cyanoacetamide derivative (I) and of at least one above mentioned covering product according to the covering substance: active substance (I) ratios ranging from about 1: 1 to about 100: 1.

They also contain the usual formulation components and / or additives.

The compound of formula (I) can exist in two stereoisomeric forms "sin" and "anti"; the use of their mixtures in all ratios falls within the spirit of the invention.

The compound of formula (I) can be prepared by operating in accordance with the methods described in European patent application 250744 cited above, by direct nitrosation of the compound of formula (II):

with an alkaline or lower alkyl nitrite and methylation of the oxime thus obtained.

The compound of formula (I) is endowed with a remarkable fungicidal activity, in particular with regard to fungi belonging to the class of Oomycetes.

It is well tolerated by plants in which it acts with systemic activity following applications that can be of a preventive, curative or eradicating nature.

It also has, compared to known isonitrosocianoacetamides, a much higher efficacy in protecting plants from the attack of pathogenic fungi.

Depending on the type of application, this efficacy is manifested either through the application of lower doses or through longer efficacy times.

For practical uses in agriculture, it is often useful to have fungicidal compositions containing the compound of formula (I) as active substance and the covering substances, defined above.

The application of these compositions can take place on any part of the plants, for example leaves, stems, branches and roots, or on the seeds themselves, before sowing, or even on the soil in which the plant grows. It is possible to use compositions in the form of dry powders, wettable powders, emulsifiable concentrates, pastes, granulates, solutions, suspensions, etc .: the choice of the type of composition will depend on the specific use. The compositions are prepared in a known manner, e.g. diluting or dissolving the active substance (I) and the cover substance with a solvent medium and / or a solid diluent, possibly in the presence of surfactants. As solid diluents, or supports, the following can be used: silica, kaolin, bentonite, talc, diatomaceous earth, dolomite, calcium carbonate, magnesia, gypsum, clays, synthetic silicates, attapulgite, sepiolite. As liquid diluents, in addition of course to water, various types of solvents can be used, for example aromatics (benzol, xylols or mixtures of alkibenzols), chloroaromatics (chlorobenzol), paraffins (petroleum fractions), alcohols (methanol, propanol) , butanol), amines, amides (dimethylformamide), ketones (cyclohexanone, acetophenone, isophorone, ethyl amyl ketone), esters (isobutyl acetate). As surfactants: sodium, calcium or triethanol amine salts of alkylsulfates, alkylsulfonates, alkylaryl sulphonates, polyethoxylated alkylphenols, fatty alcohols condensed with ethylene oxide, polyoxyethylated fatty acids, polyoxyethylated sorbitol esters, polyoxyethylated fats, lignosulfonates. The compositions can also contain special additives for particular purposes, for example tackifying agents such as gum arabic, polyvinyl alcohol, polyvinylpyrrolidone.

If desired, it is possible to add to the compositions object of the present invention also other compatible active substances such as fungicides, pesticides, plant growth regulators, herbicides, insecticides, fertilizers.

The concentration of active substance in the above compositions can vary within a wide range, depending on the active compound, the culture, the pathogen, the environmental conditions and the type of formulation adopted. In general, the concentration of the sum of the covering substance plus the active substance varies between 0.1 and 95%, preferably between 0.5 and 90% by weight, with respect to the total weight.

The following examples illustrate the invention.

EXAMPLE

a) Synthesis of N- (1- (3-tetrafluoroethoxy) propyl) 2-methoxyiminocyanoacetamide.

A solution of N- (1- (4-tetrafluoroethoxy) propyl) -2-hydroxyiminoacetamide (2.0 g), potassium carbonate (0.87 g), dimethyl sulfate (0.79 g), 18-corona-6-ether (0.05 g) in acetone (25 cc) is heated to 40 ° C and stirred at this temperature for 50 minutes. It is then cooled, filtered and the filtrate evaporated. The residue, taken up with dichloromethane, is washed 3 times with water. The organic phase is anhydrated on sodium sulphate, the solvent is evaporated until a very viscous liquid is obtained, which crystallizes by adding ethyl ether. It is filtered and a white, crystalline product (0.9 g) is obtained.

Characterization:

b) Determination of the curative fungicidal activity against Plasmopora viticola (B. and C.) Berl, et de Toni, in the presence of covering fungicides.

The vine leaves cv. Dolcetto, grown in pots in a conditioned environment at 25 ° C and 60% R.H. they were sprayed (inoculated) on the lower side with an aqueous suspension of Plasmopora viticola conidia (200,000 conidia / cc); after 24 hours of permanence in an environment saturated with humidity, at 21 ° C, they were treated by spraying both pages with compound (I) and the covering product in question in hydroacetonic solution (20% of acetone vol./vol .), in the doses and compositions indicated in tables 1 and 2. Then the plants were transferred to 70% R.H. and 21 ° C for the incubation period (7 days).

Finally, the Intensity of Infection was evaluated, with indices on an evaluation scale ranging from 100 (healthy plant) to 0 (completely infected plant).

Table 1 shows the results of the determinations carried out with the compound (I) alone and in mixture with the copper oxychloride covering, compared with the corresponding activity of the cyanoacetamide compounds of formula:

reported in table 1, no. 4,5,6, of EP-250744, also used as such or in a mixture with copper oxychloride of the same composition.

Table 2 shows the activities of compound (I) in admixture with Mancozeb in comparison with compound (C).

Table 1 - 1 day curative ACTIVITY of the active substance and the OXYCHLORIDE COPPER MIXTURE

Table 2 - 1 day curative ACTIVITY of the active substance and the MIXTURE WITH MANCOZEB.

(B-786-004) 10

Claims (4)

CLAIMS 1. Antifungal mixtures containing the compound: and at least one covering fungicide selected from: ethylene bis (dithiocarbamate) of manganese and zinc, ethylene bis (dithiocarbamate) of manganese, ethylene bis (dithiocarbamate) of zinc, dimethylthiocarbamate of zinc, oxide (I) of copper. 2. Antifungal composition according to claim 1, wherein in the mixture the ratio of the compound (I) to the covering fungicide is comprised between 1: 1 and 100: 1 by weight. 3. Method for fighting fungal infections in useful plants consisting in distributing on the plants, on their organs or seeds, when the fungal infection is foreseen or already in progress, an effective quantity of the mixture according to claims 1 and 2 as such or in the form of suitable composition. 4. Antifungal compositions containing the active ingredient according to claims 1 and 2, alongside an inert solid or liquid carrier and possibly other additives and / or active substances, according to quantities between 0.1% and 95% with respect to the total weight .