Use of a fungicidal composition for the curative treatment of fungal diseases in plants

Abstract: A fungicidal composition in particulate or powder form wherein each active particle thereof comprises a fungicidally active compound, especially an acrylamide such as dimethomorph, dispersed in a polymer material having a melting point below the degradation temperature of the compound. The fungicidal composition is particularly useful in the form of a wettable powder or a suspension concentrate.

Description: The present inventation relates to the use of certain fungicidal compositions in combating fungal infections in plants. The present invention is concerned with the problem of formulating fungicides especially of the acrylamide type - see European Patent EP-A-120321 - so that the inherent activity of the fungicide is maintained in an effective manner. It is well known that fungal diseases in agricultural crops can be combated by the use of properly formulated active materials. Generally, these fungicidal formulations have to be applied early, before infection of the plant has taken place. Some diseases, however, are prompted by particular weather conditions - for instance heavy rainfalls, dry periods - and there is constant risk that an infection will occur earlier than expected. In unfavourable cases, an infection could have taken place before the fungicide was applied or before it was actually transported to its site of action. In that case, it is an undoubted advantage if an active material also acts after infection has taken place. Such an activity of a fungicide is called curative activity, in contrast to the ordinary performance which is called prophylactic activity. It is well known to incorporate crop protection active ingredients in a polymeric material and use in ground form in order to control the release of the active ingredient and thereby prolong its action or prevent injurously-high initial dose application to plants, see, for example, FR-A-1 022 969, US-A-4 297 339, EP-A-0 021 477, GB-A-2 164 257 and EP-A-0 120 610. A formulation of active ingredient in a polymeric material has now been found which maintains the inherent activity of a specific acrylamide fungicide, in an effective manner so that the prophylactic action occurs with consistency and significantly enhances the curative action of the active ingredient in comparison to a similar solid formation of higher active ingredient content but with no incorporated polymeric material. Accordingly the present invention provides the use of a fungicidal composition in particulate or powder form wherein each active particle thereof comprises 3-(3, 4-dimethoxyphenyl)-3-(4-chlorophenyl) acrylic acid morpholide dispersed in a polymer material selected from polylactic acid and wood rosin wax, for the curative treatment of fungal diseases in plants. For application, such a composition is normally formulated as a wettable powder or suspension concentrate and thus the invention also includes the use of such a fungicide composition which additionally includes at least one inert carrier, preferably at least two carriers one of which is a surface active agent. The particle size of the fungicidal composition according to the invention will depend on the nature of the formulation. Generally speaking, the particle size will vary between 0.1 to 50 µm, preferably from 0.3 to 30 µm. In a wettable powder formulation a typical particle size range is 3 to 30 µm, preferably 5-15 µm whereas for a suspension concentrate the particle size range is 0.3 to 5 µm preferably 0.5 to 2.5 µm. The concentration of the fungicidally active compound in the polymer material may vary widely; suitably it is in the range 10 to 90 % by weight but is preferably in the range 25 to 75% by weight of the compound plus polymer material. For ease of application, and as mentioned earlier, the fungicidal composition according to the invention may additionally comprise at least one inert carrier for the particulate or powder material, preferably at least two carriers one of which is a surface active agent. The carrier may be a solid or liquid material, which may be inorganic or organic and of synthetic or natural origin. Typical solid carriers include natural and synthetic clays and silicates, for example natural silicas, for example diatomaceous earths, and aluminium silicates, for example kaolinites, montmorillonites and micas. Typical liquid carriers are ketones, for example methylnaphthalenones, and petroleum fractions, for example petroleum xylenes and light mineral oils. Also water may be a liquid carrier. Mixtures of liquids are often suitable. One or more surface active agents and/or stickers can be included in the composition. The surface active agent may be a dispersing agent or a wetting agent; it may be non-ionic or ionic. Any of the surface-active agents usually applied in formulating pesticides may be used. Examples of surface-active agents are the sodium and calcium salts of polyacrylic acids and lignin and sulphonic acids; the condensation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol, condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohols or alkyl phenols, for example p-octylphenol or p-octylcresol, with ethylene oxide and/or propylene oxide; sulphates or sulphonates of these condensation products; alkali or alkaline earth metal salts, preferably sodium salts, of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulphate, sodium secondary alkyl sulphates, sodium salts of sulphonated castor oil, and sodium alkylaryl sulphonates such as sodium dodecylbenzene sulphonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide. The composition may be formulated as a wettable powder, microcapsules, a dust, granules, an emulsifiable concentrate, an emulsion or a suspension concentrate. Preferred formulations for a composition according to the present invention are a wettable powder or a suspension concentrate. Wettable powders usually contain 25, 50 or 75%w of active ingredient and may contain in addition to inert solid material, 3-10%w of a dispersing agent and, when necessary, 0-10% w of a stabiliser, a penetrant and/or sticker. A suspension concentrate is a stable non-sedimenting, flowable product and usually contains 10-75%w active ingredient, 0.5-15%w of dispersing agent, 0.1-10%w of suspending agent, for example protective colloid and/or thixotropic agent, and 0-10% of other additives including, for example, a biocide, a defoamer, a corrosion inhibitor, a stabiliser, a penetrant and/or sticker, and as dispersant, water or an organic liquid in which the active ingredient is substantially insoluble; certain organic additives and/or inorganic salts may be dissolved in the dispersant to assist in preventing sedimentation or as anti-freeze for water. In the formulated condition, the compositions may contain from 1.0% to 80% by weight of active ingredient, preferably in the range 20% to 60%. If another active ingredient is present then the preferred range is likely to be 5% to 40% by weight. Especially good results in terms of curativity of fungal diseases have been obtained with compositions comprising the specified active ingredient in a concentration ranging from 0.1% to 99% of the composition as fungicidal component. With this compound the best results could be achieved with a concentration of the fungicide in the range of from 10% to 50% by weight of the composition and a polymer concentration ranging from 5% to 50% of the composition. The dispersion of the fungicidally active compound in the polymer material may be obtained by any of the known melting and/or blending procedures. However, it is advantageous to melt the fungicidal compound together with the selected polymer material, optionally in the presence of adjuvants and auxilliaries, and then to chill the melt below the melting temperature of the mixture. Subsequently, the quenched melt may be ground to produce a particulate or powder form of the melt according to known methods. The production of the formulation for use by the farmer can be carried out by methods known for the formulation of agrochemical compounds. The compositions may be used for the anative treatment of any fungal disease of plants, especially of vines. If desired the fungicidally active compound can be admixed with one or more different fungicidally active compounds to compliment the spectrum of activity of the first compound. This mixture of active ingredients can be incorporated into the same polymer particle and then formulated according to known techniques, or, alternatively, the mixture can be achieved by separately incorporating the different active ingredients into polymer particles and blending the different sets of polymer particles together. The following Examples further illustrate the compositions, means for their preparation and their use according to the invention: Example 1 Preparation Example 3-(3,4-Dimethoxyphenyl)-3-(4-chlorophenyl)-acrylic acid morpholide (10g) was mixed with finely powdered polylactide (10g; Resomer 18 L, Boehringer Ingelheim, Ingelheim, F.R.G.) and then was heated in a beaker to 150°C. After 5 min a low viscous, neat melt was formed which was poured out onto a cold glass plate. It solidified well on cooling and was then broken into pieces. In order to prepare a wettable powder, the pieces were ground in a mortar to form a powder of the melt. Example 2 25% Wettable Powder formulation 25% 3-(3,4-dimethoxyphenyl)-3-(4-chlorophenyl)-acrylic acid morpholide (common name: dimethomorph) 25% polylactic acid (M.W. 1000 - 10000) 2% wetting agent (sodium alkylnaphthenesulfonate) 8% dispersing agent (calcium lignosulfonate) 20% silicic acid (carrier) 20% kaolin (carrier) Before formulation, the active ingredient was dispersed in the polymer and ground to a powder according to the method of Example 1. Example 3 25% Wettable Powder Formulation 25% 3-(3,4-dimethoxyphenyl)-3-(4-chlorophenyl)-acrylic acid morpholide (common name: dimethomorph) 25% wood rosin wax (m.p. 70-120°C) 2% wetting resin (sodium alkylnaphthenesulfonate) 8% dispersing agent (calcium lignosulfonate) 20% silicic acid (carrier) 20% kaolin (carrier) Before formulation, the active ingredient was dispersed in the polymer and ground to a powder according to the method of Example 1. Comparative example 50% wettable powder 50% 3-(3,4-dimethoxyphenyl)-3-(4-chlorophenyl)-acrylic acid morpholide (common name: dimethomorph) 2% wetting agent (sodium alkylnaphthenesulfonate) 8% dispersing agent (calcium lignosulfonate) 20% silicic acid (carrier) 20% kaolin (carrier) Biological Testing Curative Activity of Fungicidal Composition against Plasmopara viticola Test plants : Cuttings of the vine cultivar Müller-Thurgau were grown in the greenhouse at 25°C and 50%-70% relative humidity. Plants were cultivated in plastic pots (diam. 12 cm). When 6-8 leaves had developed the plants were cut back to 3-4 equally sized leaves. Infection : The plants were artificially infected with an aqueous spore suspension of Plasmopara viticola containing 200,000 spores/ml. Infection was accomplished by spraying the lower side of leaves with the spore suspension. Then the plants were immediately incubated at 100% relative humidity for 48 hours. Application : 4-6 plants per treatment were used. Application of the fungicidal compositions was carried out 48 hours after infection. The test plants were sprayed to run off in a spray cabinet using 20 ml of spray wash. Then the plants were kept at high humidity in the greenhouse at 23°C day and 18°C night temperature until symptoms developed (approx. 5-6 days after infection). Evaluation : Evaluation was carried out by estimating the percentage of diseased leaf area of each individual leaf. The activity in % was calculated using the formula: Results : Curative activity of several formulations against Plasmopara viticola in vines (concentration active ingredient: 150 ppm). Activity Example 2, WP 25 50% Example 3, WP 25 60% Comp. example, WP 50 <10% These results illustrate the superior curative activity of the fungicidal compositions according to the invention over the known formulation.

Claims: Claims for the following Contracting States : AT, BE, CH, DE, DK, FR, GB, GR, IT, LI, LU, NL, SE The use of a fungicidal composition in particulate or powder form wherein each active particle thereof comprises 3-(3, 4-dimethoxyphenyl)-3-(4-chlorophenyl) acrylic acid morpholide dispersed in a polymer material selected from polylactic acid and wood rosin wax for the curative treatment of fungal diseases in plants. The use of a composition according to claim 1, wherein the concentration of the 3-(3, 4-dimethoxyphenyl)-3-(4-chlorophenyl) acrylic acid morpholide in the polymer material is in the range 25 to 75% by weight of the compound plus polymer material. The use of a composition according to claim 1 or claim 2, wherein it additionally comprises at least one inert carrier, or at least two carriers one of which is a surface active agent. The use of a composition according to claim 3, wherein 3-(3, 4-dimethoxyphenyl)-3-(4-chlorophenyl) acrylic acid morpholide is present in a concentration in the range of from 10% to 50% by weight of the composition. Claims for the following Contracting State : ES A process for treating plants for the curative treatment of fungal diseases, which comprises applying to the plants a fungicidal composition in particulate or powder form, wherein each active particle thereof comprises 3-(3,4-dimethoxyphenyl)-3-(4-chlorophenyl) acrylic acid morpholide dispersed in a polymer material selected from polylactic acid and wood rosin wax. A process according to Claim 1, wherein the concentration of the 3-(3,4-dimethoxyphenyl)-3-(4-chlorophenyl) acrylic acid morpholide in the polymer material is in the range 25 to 75% by weight of the compound plus polymer material. A process according to Claim 1 or Claim 2, wherein said fungicidal composition additionally comprises at least one inert carrier, or at least two carriers one of which is a surface active agent. A process according to Claim 3, wherein 3-(3,4-dimethoxyphenyl)-3-(4-chlorophenyl) acrylic acid morpholide is present in a concentration in the range of from 10% to 50% by weight of the composition. A process according to any preceding claim, wherein the plants being treated are vines.

Inventors: ALBERT GUIDO, FRIEDRICHS EDMUND, ALBERT, GUIDO, FRIEDRICHS, EDMUND
Applicants: SHELL INT RESEARCH, SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.
Application year: 1990
Main classification: A01N25
IPC codes: A01N25, C07D295, A01N43, C08K9, A01N37