TW201720304A - Agent and method for reducing the E/Z isomerization of dimethomorph - Google Patents

Abstract

A method of reducing the E/Z isomerization of dimethomorph is provided, the method comprising applying dimethomorph together with fosetyl-aluminium. There is also provided a method of reducing the instability of the fungicidal activity in the presence of light of dimethomorph, the method comprising contacting dimethomorph with fosteyl-aluminium. There is further provided a method of preventing or reducing fungal infestations of plants at a locus, the method comprising applying to the locus dimethomorph and fosetyl-aluminium. A composition comprises dimethomorph and fosetyl-aluminium.

Description

Medicament and method for reducing dawfene E/Z isomerization

The present invention provides an agent for reducing E/Z isomerization of dafoxdine. The invention further relates to a composition comprising an E and/or Z isomer of dafoxdine and a conversion reagent. The invention also relates to a method of reducing E/Z isomerization of dafoxdine.

Agrochemically active compounds such as pesticides are often exposed to sun exposure after outdoor application. In the case of some active compounds, this leads to a reduction in their pesticidal activity.

( EZ )-4-[3-(4-Chlorophenyl)-3-(3,4-dimethoxyphenyl)propenyl]morpholine, commonly known as dafoxdine, is a known fungicidal Agent. Daxafen can exist as the E and Z isomers as shown below.

However, only the Z isomer of daxen is inherently active as a fungicide. Upon photoirradiation, the initially applied Z isomer is isomerized to the E isomer.

It has been found that dafoxdine loses its activity after light irradiation. More specifically, the photoirradiation effect of daxen is to convert the Z isomer to the E isomer, resulting in loss of fungicidal activity.

Therefore, a technique is needed to increase the stability of daphtene when exposed to light. In particular, there is a need for a technique to reduce the isomerization of daxanfloxacin after exposure to light, more particularly E/Z isomerization.

Surprisingly, it has now been found that E/Z isomerization after exposure to light can be reduced by the use of reagents, in particular Forsyth. In particular, it has been found that the administration of dafoxim and forsylide to the locus to be treated (for example by means of a composition comprising both dadefon and forsydine) significantly reduces the dextrofenate exposure to light. Isomerization, especially the conversion of the Z isomer to the E isomer. This in turn maintains the fungicidal activity of the damefen active ingredient.

Accordingly, in a first aspect, the present invention provides a method of reducing E/Z isomerization of daxifen comprising administering daphex in addition to forsydine.

In a second aspect, the present invention provides a method of reducing the instability of the fungicidal activity of danufen in the presence of light, the method comprising contacting daphtene with forsydine.

In another aspect, the invention provides a method of preventing or reducing fungal infestation of a plant at a site, the method comprising administering to the site daxenfene and forsydine.

In another aspect, the invention provides a composition comprising daphoff and forsythia.

Furthermore, the present invention provides for the use of forsylate to reduce the E/Z isomerization of dafoxdine.

The E/Z isomerization of daxen is understood to mean the double bond conversion from the E isomer to the Z isomer or from the Z isomer to the E isomer. It has been found that the presence of forsydine significantly reduces the conversion of the Z isomer to the E isomer of dafox. In addition, it has been found that the E in Dafenfen In the case of a mixture with the Z isomer, the presence of forsythia can increase the amount of the Z isomer over time.

If the weight ratio of the Z isomer to the E isomer of dasphene in the presence of Forsylate is more slowly reduced than the change in the ratio in the absence of Forsyth, or the Z isomer and E The weight ratio of the isomers remains the same or increases compared to their initial values, and a reduction in the E/Z isomerization of daphtene is achieved.

In the present invention, dadoffene may be employed or present as the E isomer, the Z isomer or a combination of the two isomers. The E and Z isomers may be present in the daxenfene component in any relative amount. The E or Z isomer of dasphene may be at least 5 wt.%, preferably at least 10 wt.%, more preferably at least 20 wt.%, more preferably based on the total amount of the dadifene-containing E and Z isomers. It is present in the composition in an amount of at least 30 wt.%, more preferably at least 40 wt.%, particularly preferably at least 50 wt.%. These values relate to the amount of isoflavone isomer present initially (ie, when daphtene is combined or contacted with forsydine).

In one aspect, the invention provides a composition comprising daphoff and forsythia. Dadextrin can be present in the composition in any suitable amount to provide the desired fungicidal activity. Daxafen may be present in the composition in an amount of at least 0.1 wt.%, more preferably at least 1 wt.%, more preferably at least 2 wt.%, more preferably at least 3 wt.%. Daxafen may be present in an amount up to 99 wt.%, preferably up to 90 wt.%, more preferably up to 80 wt.%, more preferably up to 75 wt.%. The amount of dafoxen may be from 0.1 wt.% to 99 wt.%, preferably from 1 wt.% to 70 wt.%, more preferably from 1 wt.% to 50 wt.%, more preferably from 1 wt.% to 30 wt.%. %, more preferably from 1 wt.% to 10 wt.%. In one embodiment, dafoximene is present in the composition in an amount of 7 wt.% of the composition.

As discussed above, the presence of forsydine reduces or prevents the conversion of the Z isomer to the E isomer of daxen, and can promote the conversion of the E to Z isomer. Without wishing to be bound by any particular theory, it is believed that Forsyth can produce an E isomer that attacks daxen. The double bond and the group that allows the single bond to rotate. Forsyth can be used in pure form as an industrial grade mixture.

As indicated above, in one aspect of the invention, a composition comprising daphoff and forsydine is provided. In the compositions of the present invention, forsydine can be present in any suitable amount to maintain the desired fungicidal activity of the dafphene fungicide. Fused can be present in an amount of from 0.1 wt.%, preferably from 1 wt.%, more preferably from 5 wt.%, more preferably from 10 wt.%, more preferably from 20 wt.%, of the composition. Forsyth can be present in an amount up to 99 wt.%, preferably up to 90 wt.%, more preferably up to 80 wt.%, more preferably up to 75 wt.%, more preferably up to 70 wt.%. Forsyth may be from 0.1 wt.% to 99 wt.%, preferably from 1 wt.% to 80 wt.%, more preferably from 30 wt.% to 70 wt.%, more preferably from 50 wt.% to 60 wt.%, in the composition. The amount exists.

As indicated above, in the present invention, the effect of forsylate is to reduce the conversion of the Z isomer to the E isomer of daxen and to increase the conversion of the E to Z isomer. In the present invention, the initial daxan may be used in the form of a Z isomer, an E isomer or a mixture of the two isomers. In the case where the Z isomer of dafoxen is present in the original dahfafin material, the effect of the fusate is to maintain the presence of the Z isomer. In the case where the E isomer of daxen is present in the original damethacin material, the effect of forsylate is to convert the E isomer to the Z isomer, thereby maintaining or increasing the presence of Z isomerism. The amount of body.

It is preferred to use dafoxdine in a form that at least partially comprises the Z isomer. In this way, dafene has fungicidal activity from the beginning.

Preferably, the initial dafoxfen material comprises at least 10 wt.% Z isomer, more preferably at least 20 wt.%, more preferably at least 30 wt.%, more preferably at least 40 wt.%, particularly preferably at least 50 wt.%. The initial daxanfene material can include a higher amount of Z isomers, such as at least 60 wt.%, 70 wt.%, 80 wt.%, or 90 wt.%. The initial dafoxdine material can consist essentially of the Z isomer. Alternatively, the initial damastoin material can be substantially composed of E Isomer composition, although this is not a preferred specific example.

The amount of the Z isomer will generally vary, more preferably increase, under the action of Forsydine. Preferably, the amount of the forsylate is such that, after contact with dafoxdine, the Z isomer of dafoxdine is present in an amount of at least 50 wt.%, more preferably at least 60 wt.%, of the daphoff material. More preferably, it is an amount of at least 70 wt.%, more preferably at least 80 wt.%, particularly preferably at least 85 wt.%, and at least 90 wt.%. The Z isomer having a higher pesticidal activity is preferably present in excess.

The present invention may employ a composition comprising daphoff and forsythia. Alternatively, or in addition, the present invention may employ dafoxdine and forsydine provided by separate compositions.

The compositions for use in the present invention may be formulated in any of the types conventional for agrochemical formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes, and granules. The type of formulation will depend on the particular intended use and should provide a fine and uniform distribution of the active ingredients, fulce and daxen. Examples of suitable types of compositions are aqueous solutions (SL), emulsions (EC), water-based emulsions (EW), microemulsions (ME), aqueous suspensions (SC), water-dispersible oil suspensions (OD), flowable Aqueous suspension (FS), water-dispersible granules (WG), water-soluble granules (SG), wettable powders (WP), water-soluble powders (SP), granules (GR), capsule granules (CG) Fine granules (FG), large granules (GG), concentrated suspoemulsion (SE), capsule suspension (CS) and microgranules (MG). Preferred formulation types are water-dispersible granules (WG) and aqueous suspensions (SC).

As indicated above, as an alternative to the compositions of the present invention, forsy and daxen may be used separately, for example by applying separate formulations to a locus, or by combining prior to application to the locus (eg When preparing a tank mix). In this case, each of the above-mentioned types of preparations may be used in each of the above-mentioned types of preparations.

These formulations may further comprise auxiliaries as are known in the art for plant protection compositions, the choice of which depends on the type of formulation and its expectation use. Typical adjuvants include extenders, carriers, solvents, surfactants, stabilizers, antifoaming agents, antifreeze agents, preservatives, antioxidants, colorants, thickeners, solid binders, and inert fillers. Such adjuvants are known in the art and are commercially available. Their use in the formulation of the compositions of the invention will be clear to those skilled in the art.

These compositions may further comprise one or more inert fillers. Such inert fillers are known in the art and are commercially available. Suitable fillers include, for example, natural ground minerals such as kaolin, alumina, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth; or synthetic ground minerals such as highly dispersed tannins. , alumina, citrate and calcium phosphate and hydrogen phosphate. Suitable inert fillers for granules include, for example, comminuted and classified natural minerals such as calcite, marble, pumice, sepiolite and dolomite; or synthetic particles of inorganic and organic ground materials; and organic materials such as sawdust, Granules of coconut shells, corn cobs and tobacco stems.

These compositions optionally include one or more surfactants, preferably nonionic, cationic and/or anionic in nature; and a surfactant mixture having good emulsifying, dispersing and wetting characteristics. The choice of surfactant depends on the type of formulation and the intended use. Suitable surfactants are known in the art and are commercially available.

Suitable anionic surfactants can be both so-called water soluble soaps and water soluble synthetic surface active compounds. The soap which can be used is an alkali metal salt, an alkaline earth metal salt or a substituted or unsubstituted ammonium salt of a higher fatty acid (C ₁₀ to C ₂₂ ), such as a sodium or potassium salt of oleic acid or stearic acid or a mixture of natural fatty acids. The surfactant may be an ionic or nonionic emulsifier, dispersant or wetting agent. Examples which may be used are salts of polyacrylic acid, salts of ligninsulfonic acid, salts of benzenesulfonic acid or naphthalenesulfonic acid, condensation polymers of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (especially Alkylphenols), sulfosuccinates, taurine derivatives (especially alkyl taurate) or polyethoxylated phenols or phosphates of alcohols. At least one surfactant is typically required when the active compound and/or inert carrier and/or adjuvant/adjuvant are insoluble in water and the final application vehicle of the composition is water.

The composition optionally further comprises one or more polymeric stabilizers. Suitable polymeric stabilizers that can be used in the present invention include, but are not limited to, polypropylene, polyisobutylene, polyisoprene, copolymers of monoolefins and diolefins, polyacrylates, polystyrene, polyvinyl acetate, Polyurethane or polyamide. Suitable stabilizers are known in the art and are commercially available.

It is believed that the surfactants and polymeric stabilizers mentioned above generally impart stability to the composition, thereby allowing for formulation, storage, transportation, and application of the composition.

Suitable antifoaming agents include all materials which are normally used in agrochemical compositions for this purpose. Suitable antifoams are known in the art and are commercially available. A particularly preferred antifoaming agent is a mixture of polydimethyl siloxane and a perfluoroalkylphosphonic acid such as an anthrone defoamer available from GE or Compton.

Suitable organic solvents are selected from all customary organic solvents which are sufficient to dissolve the active compound employed. Further, suitable organic solvents for dafoxdine and forsydine are known in the art. It mentioned below may be preferred: N- methylpyrrolidone, N- octyl pyrrolidone, cyclohexyl-1-pyrrolidone; or a mixture of paraffins, isoparaffins, cyclic paraffins and aromatic hydrocarbon SOLVESSO ^TM 200. Suitable solvents are commercially available.

Suitable preservatives include all materials which are commonly used for this purpose in this type of agrochemical composition and are also well known in the art. Suitable examples which may be mentioned include PREVENTOL ^® (from Bayer AG) and PROXEL ^® (from Bayer).

Suitable antioxidants include all materials which are commonly used for this purpose in agrochemical compositions, as is known in the art. Preferred is butylated hydroxytoluene.

Suitable thickeners include all materials which can normally be used for this purpose in agrochemical compositions. For example, xanthan gum, polyvinyl alcohol (PVOH), cellulose and its derivatives, clay hydrated citrate, magnesium alumininate or mixtures thereof. Again, such thickeners are known in the art and are commercially available.

The composition can be administered by methods known in the art. These methods include spraying, dusting, spreading, brushing, pouring, coating, spraying, dipping, soaking, injecting, and irrigating.

Forsyth can be contacted with dafoxdine at any stage during the preparation and use of the present invention. For example, the two components can be combined in a single composition. Alternatively, the two components can be applied separately and combined at the site. As a further alternative, the two components can be brought into contact with each other immediately prior to use, for example by way of a tank mix.

The rate of application (use) of forsylate and daxen in the present invention may vary, for example, depending on the type of use, the type of crop, the particular active compound employed, and the type of plant, but should be such that the active compound in combination is provided It is desirable to administer an effective amount (e.g., disease or pest control) for administration. The amount of component application for a given set of conditions can be readily determined by experimentation.

Suitable application rates for each of dafphene and forsydine are in the range of 50 to 5000 g/ha. The preferred combination application rate for both dafoxim and forsyth is from 500 to 5000 g/ha.

In general, satisfactory results will be obtained when using from 100 to 400 g/ha, for example 210 g/ha of dafoxen and from 750 to 3000 g/ha of forsyth, for example 1500 or 1800 g/ha .

The present invention can be used for the prevention and/or treatment of diseases caused by a wide range of fungal pathogens such as, but not limited to, Cuban pseudomonas (downy mildew); Phytophthora; in cucurbits like melon, watermelon, Cuban fake downy mildew on courgettes, squash and cucumbers; in fruits such as apples, avocados, black raspberries, blackberries, blueberries, citrus, cranberries, grapes, vines, peaches, pineapples, raspberries, red raspberries And Phytophthora, Rhizoctonia solani, V. vascularis, blister spot (Pseudomonas syringae pimples), Phytophthora root rot (Strawberry berry), Phytophthora root Rot (Phytophthora species), Rhizoctonia (Strawberry raspberry), Phytophthora root rot (Pythium cinerea), Anthrax fruit rot (C. anthracis), Pseudomonas spp. (Bilberry) Pseudomonas spp.), neck rot (Pythium falciparum), rot disease (Pythium pipiens), root rot (parasitic Phytophthora sojae), downy mildew (grape downy mildew), crown rot (Pythium velutiform) ), root rot (Phytophthora species); Phytophthora root rot on ginseng; Pythium, Phytophthora, crown rot and on ornamental plants Rot (Phytophthora sp.), Phytophthora rot (Phytophthora camphor), air Phytophthora (Phytophthora species, including sudden oak death pathogen (Phytophthora ramorum), Bradley Phytophthora (Phytophthora drechsleri), Phytophthora nicotianae Mold and parasitic Phytophthora), Phytophthora root, crown rot and stem rot (Phytophthora species), downy mildew (Pleurotus, Pseudomonas, Downy Mildew and Monotrichum species), Downy mildew (dendritic fungus), downy mildew (Pseudomonas sinensis); Penicillium on tobacco (Tobacco downy mildew); Pythium on turf, foliar and basal rot anthracnose, cut Stranded dead spots; Alternaria leaf spot on vegetables (Alternaria species), anthracnose (Anthracnose species, Potato anthracnose, Anthrax anthracis, Agaricus bisporus, a small plexus shell [ teleomorph], two plate Aeromonas lettuce), group Botrytis rot (Botrytis cinerea), downy mildew (lettuce disc pullulans, spinach Creme mildew (Peronospora farinose f.sp.Spinaciae), parasitic transparent cream Hyaloperonospora parasitica , Peronospora parasitica , Peronospora destructor , Peronosp Ora destructor ), Pseudoperonospora cubensis , Bremia lactucae , Downy Mildew species, early blight (Alternaria solani), Bacterial wilt (melon blight), late blight ( Phytophthora infestans, leaf blight ( Botrytis squamosal ), leaf spot (Poly and genus var.andina ), Phytophthora root rot Mildew species, Phytophthora lucidum), purpura (Alternaria spp.), septoria leaf spot (Acanthopon species), white rust ( Albugo occidentalis ), The vegetables such as Chinese cucumber, balsam pear, bitter gourd, belgian chicory, pakchoi, eucalyptus leafy vegetables, broccoli, cabbage cabbage, cabbage, cabbage (China (napa)), cabbage (Chinese mustard), Roman melon , cauliflower, Cavallo broccoli, Chinese winter melon, medlar watermelon, gourd, edible gourd, eggplant, garlic, garlic (big head), cucumber, ground cherry, kohlrabi, leeks, lettuce, melon, onion, onion (dry ball), onion (green), onion (Welch) Qiegua, peppers, potatoes, turnips, onions, spinach, zucchini, green tomatoes, tomato, and butternut squash.

Furthermore, the present invention finds use of preventing and/or treating diseases caused by fungal pathogens such as, but not limited to, fruits such as grape downy mildew (downy mildew) on grapes; vegetables such as tomatoes, eggplants, and peppers Phytophthora infestans (late blight); and cucumber downy mildew (downy mildew) on Cucurbitaceae such as melon, watermelon, courgette, pumpkin and cucumber.

The invention has a number of advantages. First, the isomerization rate of Z-E of daxen is significantly reduced. As a result, the applied dafoxdine material remains active for longer in sunlight. Another result is that the rate of application of dasphenein can be reduced.

Dafoxim and forsythine can be applied simultaneously or continuously to the plants, plant parts and/or surroundings desired to be controlled at short intervals, for example on the same day. Dafoxim and forsythine can be applied to the plant, one or more parts thereof (eg, leaves or seeds), or in any order. Each compound can be administered only one or more times. Preferably, Dafenfen and Forsyth They are each applied a plurality of times, particularly 1 to 5 times, more preferably 2 times.

Dafoxim and forsythine can be administered continuously or simultaneously in any desired order, in any combination. In the case of simultaneous administration of dafoxifene and forsythine in the present invention, they can be administered as a composition comprising damasfen and forsythine, in which case daphthene and forsythine can each be obtained separately from The source of the formulation is mixed and mixed together (referred to as a tank mix, ready-to-use, spray, or slurry), optionally with other pesticides; or daxen and forsyth can be provided as a source of a single formulation mixture ( It is referred to as a premix, a concentrate, a formulated compound (or product), and is optionally mixed with other pesticides.

The compositions of the present invention can be distinguished by the fact that plants are particularly well tolerated and environmentally friendly.

The invention will be further described by the following specific examples, which are presented for illustrative purposes only.

In the examples below, the indicated percentages are by weight unless otherwise stated.

Instance Example 1 - Preparation of Composition

The following compositions were prepared. Compositions 8 and 9 were prepared for comparison purposes and are not examples of the invention.

Composition 1: WDG 10% Forsyth

The water dispersible granule (WDG) formulation is prepared to have the following composition: 7% dadefen; 10% forexine; 5% sodium lauryl sulfate; 5% fatty alcohol polyglycol ether; 2% lignosulfonic acid, sodium salt, sulfomethylated; 8% ammonium sulfate 1% defoamer; 25% sucrose and 37% lactose.

Daphtene, as used to form the composition, comprises a mixture of E and Z isomers.

Composition 2: WDG 20% Forsyth

The water dispersible granule (WDG) formulation was prepared to have the following composition: 7% dadefen; 20% forsylate; 5% sodium lauryl sulfate; 5% fatty alcohol polyglycol ether; 2% wood Quality sulfonic acid, sodium salt, sulfomethylated; 8% ammonium sulfate; 1% antifoaming agent; 20% sucrose and 32% lactose.

Daphtene, as used to form the composition, comprises a mixture of E and Z isomers.

Composition 3: WDG 30% Forsyth

The water dispersible granule (WDG) formulation was prepared to have the following composition: 7% dadefen; 30% forexide; 5% sodium lauryl sulfate; 5% fatty alcohol polyglycol ether; 2% wood Quality sulfonic acid, sodium salt, sulfomethylated; 8% ammonium sulfate; 1% antifoaming agent; 17% sucrose and 25% lactose.

Daphtene, as used to form the composition, comprises a mixture of E and Z isomers.

Composition 4: WDG 50% Forsyth

The water dispersible granule (WDG) formulation was prepared to have the following composition: 7% dadefen; 50% forex; 5% sodium lauryl sulfate; 5% fatty alcohol polyglycol ether; 2% wood Quality sulfonic acid, sodium salt, sulfomethylated; 8% ammonium sulfate; 1% antifoaming agent; 9% sucrose and 13% lactose.

Daphtene, as used to form the composition, comprises a mixture of E and Z isomers.

Composition 5: WDG 60% Forsyth

The water dispersible granule (WDG) formulation was prepared to have the following composition: 7% dadefen; 60% forsylate; 5% sodium lauryl sulfate; 5% fatty alcohol polyglycol ether; 2% wood Quality sulfonic acid, sodium salt, sulfomethylated; 8% ammonium sulfate; 1% antifoaming agent; 6% sucrose and 16% lactose.

Daphtene, as used to form the composition, comprises a mixture of E and Z isomers.

Composition 6: WDG 70% Forsyth

The water dispersible granule (WDG) formulation was prepared to have the following composition: 7% dadefen; 70% forexide; 5% sodium lauryl sulfate; 5% fatty alcohol polyglycol ether; 2% wood Quality sulfonic acid, sodium salt, sulfomethylated; 8% ammonium sulfate; 1% antifoaming agent; 1% sucrose and 1% lactose.

Daphtene, as used to form the composition, comprises a mixture of E and Z isomers.

Composition 7: SC 50% Forsyth

The aqueous suspension (SC) formulation was prepared to have the following composition: 7% dadefen; 50% forexide; 10% propylene glycol; 5% tristyryl polyoxyether; 1% sodium lignosulfonate; % carboxymethylcellulose; 1% eucalyptus oil (in the form of a 75% emulsion in water); water (balanced to 1 L).

Daphtene, as used to form the composition, comprises a mixture of E and Z isomers.

Composition 8: WDG 0% Forsyth

The water dispersible granule (WDG) formulation was prepared to have the following composition: 7% dadefen; 5% sodium lauryl sulfate; 5% fatty alcohol polyglycol ether; 2% wood Sulfonic acid, sodium salt, sulfomethylated; 8% ammonium sulfate; 1% antifoaming agent; 30% sucrose and 42% lactose.

Daphtene, as used to form the composition, comprises a mixture of E and Z isomers.

Composition 9: SC 0% Forsyth

The aqueous suspension (SC) formulation was prepared to have the following composition: 7% dadefen; 10% propylene glycol; 5% tristyryl polyoxyether; 1% sodium lignosulfonate; 1% carboxymethyl cellulose 1% eucalyptus oil (in the form of 75% emulsion in water); water (balanced to 1 liter).

Daphtene, as used to form the composition, comprises a mixture of E and Z isomers.

Example 2 - Analysis of irradiation and isomerization of dafoxdine

The effect of irradiation with light on the composition of Example 1 was tested as follows: The compositions prepared in Example 1 were each diluted with water. Twenty mg of the resulting three dilutions of the sample were taken and dropped onto a glass plate and allowed to dry at room temperature. Three dry samples were then irradiated with UV or the like for 0, 25 and 100 minutes. After the irradiation, the sample was washed from the glass plate by applying ultrasonic sonication with 4 mL of dimethyl hydrazine (DMSO). The sample was separated by HPLC into the E and Z isomers of danufen. The amount of the E and Z isomers of dasphene was measured by the peak area, and the percentage of the Z isomer of daxen present present was determined for each sample. The results are shown in Table 1 below.

As can be seen from the data presented in Table 1, the presence of forsythia in the composition reduces the conversion of the E isomer of daxan to the Z isomer and results in the amount of Z isomers The experiment time is increased.

Example 3 Field trial against grape vines (Grape Downy Mildew)

The young vine plants were sprayed with a conidia suspension of the grape downy mildew and incubated at 20 ° C and 100% relative atmospheric humidity for 48 hours.

The compositions indicated below were prepared and then each diluted with water and sprayed onto the plants.

Composition A: 7% dadefen (Z isomer); 50% forsylate; 5% sodium lauryl sulfate; 5% fatty alcohol polyglycol ether; 2% lignosulfonic acid, sodium salt, Sulfonated; 8% ammonium sulfate; 1% defoamer; 9% sucrose and 13% lactose.

Composition B: 7% dadefen (Z isomer); 5% sodium lauryl sulfate; 5% fatty alcohol polyglycol ether; 2% lignosulfonic acid, sodium salt, sulfomethylated; 8% ammonium sulfate; 1% defoamer; 30% sucrose and 42% lactose.

Composition C: 50% forexine; 5% sodium lauryl sulfate; 5% fatty alcohol polyglycol ether; 2% lignosulfonic acid, sodium salt, sulfomethylated; 8% ammonium sulfate; % defoamer; 30% sucrose and 42% lactose.

Compositions B and C are for comparison purposes only and are not specific examples of the invention.

A control composition prepared according to Composition A was also prepared, but it did not contain dadefen and forsythia, and was used again for comparison purposes.

One group of plants is stored in the dark and another group of plants is stored in daylight. The two groups of plants were maintained in a greenhouse at 15 ° C and 80% relative atmospheric humidity for 7 days.

After this, the severity of the fungal infection of the plants was examined. The severity was determined as the percentage of plants exhibiting visual fungal infestation. The results are listed in Table 2 below.

As can be seen from the data in Table 2 above, compositions B and C and controls exhibited significantly reduced fungicidal effects when irradiated plants were irradiated with sunlight. In contrast, the presence of both desfenfen and forsydine in Composition A provided a high degree of fungicidal activity in both cases under dark conditions and when irradiated with sunlight.

Claims (51)

A method of reducing the E/Z isomerization of dimethomorph comprising administering daphnene together with fosetyl-aluminium. The method according to claim 1, wherein the dasphenein is present in the form of an E isomer, a Z isomer or a combination of the E isomer and the Z isomer. The method of any of the preceding claims, wherein the dadifene comprises an E isomer or a Z isomer in an amount of at least 5% by weight based on the total amount of daphthene present. The method of claim 3, wherein the dadifene comprises an E isomer or a Z isomer in an amount of at least 10% by weight based on the total amount of daphthene present. The method of claim 4, wherein the dadifene comprises an E isomer or a Z isomer in an amount of at least 40% by weight based on the total amount of daphthene present. A method according to any of the preceding claims, wherein the dadefenol initially comprises at least 10% by weight of the Z isomer. The method of claim 6, wherein the dafoxantin initially comprises at least 30% by weight of the Z isomer. A method according to any of the preceding claims, wherein the method employs a composition comprising daphoff and forsythia. The method of any one of claims 1 to 7, wherein the daphoff and the forsyth are separately applied to the locus to be treated. A method of reducing the instability of the fungicidal activity of dasphene in the presence of light, the method comprising contacting daphtene with forsydine. The method according to claim 10, wherein the daxen is present in the form of the E isomer, the Z isomer or a combination of the E isomer and the Z isomer. The method of claim 10 or 11, wherein the dadifene comprises an E isomer or a Z isomer in an amount of at least 5% by weight based on the total amount of daphthene present. The method of claim 12, wherein the dadifene comprises an E isomer or a Z isomer in an amount of at least 10% by weight based on the total amount of daphthene present. The method of claim 13, wherein the dadifene comprises an E isomer or a Z isomer in an amount of at least 40% by weight based on the total amount of daphthene present. The method of any one of claims 10 to 14, wherein the dafoxfen initially comprises at least 10% by weight of the Z isomer. The method of claim 15, wherein the dafoxantin initially comprises at least 30% by weight of the Z isomer. The method of any one of claims 10 to 16, wherein the method employs a composition comprising dadifene and forsythia. The method of any one of claims 10 to 16, wherein daphoff and forsyth are separately applied to the locus to be treated. A method of preventing or reducing fungal infestation of a plant at a site, the method comprising administering to the site daxen and forsythia. The method according to claim 19, wherein the dadifene is in the form of an E isomer, a Z isomer or a combination of the E isomer and the Z isomer. The method of claim 19 or 20, wherein the dadifene comprises an E isomer or a Z isomer in an amount of at least 5% by weight based on the total amount of daphthene present. The method of claim 21, wherein the dadifene comprises an E isomer or a Z isomer in an amount of at least 10% by weight based on the total amount of daphthene present. The method of claim 22, wherein the dadifene comprises an E isomer or a Z isomer in an amount of at least 40% by weight based on the total amount of daphthene present. The method of any one of claims 19 to 23, wherein the dafoxfen initially comprises at least 10% by weight of the Z isomer. The method of claim 24, wherein the dafoxacin initially comprises at least 30% by weight Z isomer. The method of any one of claims 19 to 25, wherein the method employs a composition comprising daphoff and forsydine. The method of any one of claims 19 to 26, wherein daphthaphen and forsythine are separately applied to the locus to be treated. The method of any one of claims 19 to 27, wherein dafoxdine is applied to the site at a rate of from 100 g/ha to 400 g/ha. The method of any one of claims 19 to 28, wherein the Forsyth is applied to the site at a rate of from 750 g/ha to 1000 g/ha. The method according to any one of claims 19 to 29, which is applied when treating or preventing the following infection: Plasmopara viticola (downy mildew) on the fruit; Phytophthora on the vegetable ( Phytophthora) Infestans ) (late blight); or Pseudoperonospora cubensis (downy mildew) on Cucurbitaceae. A composition comprising dafenac and forsydine. The composition of claim 31, wherein the dafoxdine is present in the composition in an amount of at least 1% by weight. The composition of claim 32, wherein the dafoxdine is present in the composition in an amount of at least 3% by weight. The composition of any one of claims 31 to 33, wherein dafoxdine is present in the composition in an amount up to 90% by weight. The composition of claim 34, wherein the dafoxdine is present in the composition in an amount up to 75% by weight. The composition of any one of claims 31 to 35, wherein the forsythin is present in the composition in an amount of at least 1% by weight. The composition of claim 36, wherein the forsythine is present in the composition in an amount of at least 10% by weight. The composition of any one of claims 31 to 37, wherein the forsythin is present in the composition in an amount of up to 90% by weight. The composition of claim 38, wherein the dafoxdine is present in the composition in an amount up to 75% by weight. The composition of any one of claims 31 to 39, wherein daxen is present in the form of the E isomer, the Z isomer or a combination of the E isomer and the Z isomer. The composition of any one of claims 31 to 40, wherein the dadifene comprises an E isomer or a Z isomer in an amount of at least 5% by weight based on the total amount of daphthene present. The composition of claim 41, wherein the dadifene comprises an E isomer or a Z isomer in an amount of at least 10% by weight based on the total amount of daphthene present. The composition of claim 42, wherein the dadifene comprises an E isomer or a Z isomer in an amount of at least 40% by weight based on the total amount of daphthene present. The composition of any one of claims 31 to 43, wherein the dafoxant initially comprises at least 10% by weight of the Z isomer. The composition of claim 44, wherein the dafoxfen initially comprises at least 30% by weight of the Z isomer. Forsyth is used to reduce the use of E/Z isomerization of dafox. A method of reducing the D/D isomerization of daxen, substantially as described above. A method of reducing the instability of the fungicidal activity of dasphene in the presence of light substantially as described above. A method of preventing or reducing fungal infestation of a plant at a locus substantially as hereinbefore described. A composition comprising daxanfene and forsydine substantially as hereinbefore described. A use of forsythia to substantially reduce the E/Z isomerization of dafoxdine as described above.