Patent Description:
Mildew, sclerotinia stem rot (white mold), leaf spot, fusaria, stem blight are widespread diseases in vegetable plants such as spinach, lettuce, asparagus, cabbages, carrots, onions or peppers. Early blight, fusaria, leafspot, powdery mildew are widespread diseases for tomatoes and tuber diseases (such as silver scurf and black scurf), mildew, sclerotinia, early blight are widespread diseases for potato plants.

Alternaria solani in particular is a fungal pathogen called early blight on potato and this disease produces distinctive leaf spots and can also cause stem lesions and fruit rot on tomato and tuber blight on potato. If uncontrolled, early blight can cause significant yield reductions.

Fusarium oxysporum is a fungal pathogen that attacks a broad range of host plants. The symptoms of Fusarium oxysporum are yellowing between the large veins, chlorosis, wilting or necrosis of leaves. If uncontrolled, Fusarium oxysporum can cause significant plant losses and yield reductions.

These diseases have a bad impact on the agricultural output and hence, there is a need to provide efficient alternative methods to common practices for controlling or preventing these pests in vegetable, tomato and potato plants. Thus, the current invention provides further methods for controlling or preventing infestation of vegetable, tomato and potato plants by phytopathogenic microorganisms which cause diseases such as mildew, sclerotinia stem rot (white mold), leaf spot, fusaria, stem blight, early blight, leafspot and sclerotinia.

Cyclobutylcarboxamide compounds and processes for their preparation have been disclosed in <CIT> and <CIT>. <CIT> discloses the use of certain cyclopropylcarboxamides for fungal control of, for example, Botrytis cinerea on tomato plants. It has now been surprisingly found that particular cyclobutylcarboxamide compounds disclosed in <CIT> and/or <CIT> are highly effective at controlling or preventing the infestation of okra, melon, tomato and potato plants by phytopathogenic microorganisms selected from Sphaerotheca fuliginea, Leveillula taurica, Sclerotinia sclerotiorum, Cercospora, Fusarium oxysporum and solani, Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Phytophthora infestans, Verticillium dahlia, Didymella bryoniae, Botrytis cinerea and Alternaria solani. These highly effective compounds thus represent an important new solution for farmers to control or prevent infestation of okra, melon, tomato and potato plants by diseases such as mildew, sclerotinia stem rot (white mold), leaf spot, fusaria, stem blight, early blight, fusaria, leafspot and sclerotinia.

According to the invention, there is provided a method of controlling or preventing infestation of okra, melon, tomato and potato plants by phytopathogenic microorganisms selected from Sphaerotheca fuliginea, Leveillula taurica, Sclerotinia sclerotiorum, Cercospora, Fusarium oxysporum, Fusarium solani, Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Phytophthora infestans, Verticillium dahlia, Didymella bryoniae, Botrytis cinerea and Alternaria solani, comprising applying to a crop of plants, the locus thereof, or propagation material thereof, a compound according to formula (Ic);
<CHM>
wherein.

A skilled person is aware that according to the method of the present invention, the compound of formula (Ic) is generally applied as part of a pesticidal composition. Hence, the invention provides a method of controlling or preventing infestation of okra, melon, tomato and potato plants by phytopathogenic microorganisms selected from Sphaerotheca fuliginea, Leveillula taurica, Sclerotinia sclerotiorum, Cercospora, Fusarium oxysporum, Fusarium solani, Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Phytophthora infestans, Verticillium dahlia, Didymella bryoniae, Botrytis cinerea and Alternaria solani, comprising applying to a crop of plants, the locus thereof, or propagation material thereof a pesticidal composition comprising a compound of Formula (Ic) and one or more formulation adjuvants. The invention also provides a method of controlling or preventing infestation of okra, melon, tomato and potato plants by phytopathogenic microorganisms selected from Sphaerotheca fuliginea, Leveillula taurica, Sclerotinia sclerotiorum, Cercospora, Fusarium oxysporum, Fusarium solani, Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Phytophthora infestans, Verticillium dahlia, Didymella bryoniae, Botrytis cinerea and Alternaria solani, comprising applying to a crop of plants, the locus thereof, or propagation material thereof a pesticidal composition comprising a compound of formula (Ic) and one or more formulation adjuvants.

Preferably, R11 and R12 are independently selected from chloro and fluoro;
A is pyrid-<NUM>-yl or pyrid-<NUM>-yl, which is substituted by one or two C<NUM>-C<NUM>-haloalkyl substituents.

Preferably, A is selected from
<CHM>
or
<CHM>
R13 is C<NUM>-C<NUM>-haloalkyl, preferably trifluoromethyl.

More preferably, the compound is selected from any one of compounds <NUM> to <NUM> of formula (Ic)
<CHM>
wherein R11, R12 and A are as defined in the following table:.

The method according to the present inventioncan comprise the steps.

The method according to the present invention can comprise the steps.

The invention also provides the use of a compound of formula (Ic) for controlling or preventing infestation of okra, melon, tomato and potato plants by Sphaerotheca fuliginea.

The invention also provides the use of a compound of formula (Ic) for controlling or preventing infestation okra, melon, tomato and potato plants by by Botrytis cinerea, in particular there is provided the use of a compound as defined in any one of embodiments <NUM> to <NUM> for controlling or preventing infestation of tomato plants by Botrytis cinerea.

The invention also provides the use of a compound of formula (Ic) for controlling or preventing infestation okra, melon, tomato and potato plants by Fusarium oxysporum, in particular there is provided the use of a compound of formula (Ic) for controlling or preventing infestation of okra plants by Fusarium oxysporum, more particularly there is provided the use of a compound of formula (Ic) for controlling or preventing infestation of a plant selected from tomato, okra and melon by Fusarium oxysporum.

The invention also provides the use of a compound of formula (Ic) for controlling or preventing infestation of okra, melon, tomato and potato plants by Alternaria Solani, in particular there is provided the use of a compound of formula (Ic) for controlling or preventing infestation of tomato or potato plants by Alternaria solani, more particularly there is provided the use of a compound of formula (Ic) for controlling or preventing infestation of potato plants by Alternaria solani.

The invention also provides a method for growing okra, melon, tomato and potato plants comprising applying or treating vegetable, tomato and potato plants or propagation material thereof with a compound of formula (Ic).

The preparation of the compounds according to the invention has been disclosed in <CIT> and <CIT>.

The term "halogen" represents fluoro, chloro, bromo or iodo, particularly fluoro, chloro or bromo.

The term "alkyl" or "alk" as used herein either alone or as part of a larger group (such as alkoxy, alkylthio, alkoxycarbonyl and alkylcarbonyl) is a straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, isopropyl, sec-butyl, isobutyl, tert-butyl, pentyl, iso-pentyl or n-hexyl.

The alkyl groups are suitably C<NUM>-C<NUM>-alkyl groups.

"Haloalkyl" as used herein are alkyl groups as defined above which are substituted with one or more of the same or different halogen atoms and are, for example, CF<NUM>, CF<NUM>Cl, CF<NUM>H, CCl<NUM>H, FCH<NUM>, ClCH<NUM>, BrCH<NUM>, CH<NUM>CHF, (CH<NUM>)<NUM>CF, CF<NUM>CH<NUM> or CHF<NUM>CH<NUM>.

The methods and uses according to the claimed invention are for controlling or preventing infestation of okra, melon, tomato and potato crop by phytopathogenic microorganisms selected from Sphaerotheca fuliginea, Sclerotinia sclerotiorum, Cercospora, Fusarium oxysporum, Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Fusarium solani, Phytophthora infestans, Verticillium dahlia, Didymella bryoniae, Botrytis cinerea, Alternaria solani and Leveillula taurica, including fungi that are resistant to other fungicides. Fungi that are "resistant" to particular fungicides refer e.g. to strains that are less sensitive to that fungicide compared to the expected sensitivity of the same species. The expected sensitivity can be measured using e.g. a strain that has not previously been exposed to the fungicide.

Application according to the methods or uses according to the invention is preferably to a crop of plants, the locus thereof or propagation material thereof. Preferably application is to the locus of the plant or the propagation material of the plant, more preferably to the propagation material. Application of the compounds according to the invention can be performed according to any of the usual modes of application, e.g. foliar, drench, soil, in furrow, seed treatment etc..

The compounds of formula (Ic) are preferably used for pest control at <NUM> to <NUM>/ha, preferably <NUM>-<NUM>/ha.

The compounds of formula (Ic) are suitable for use on any okra, melon, tomato and potato plant, including those that have been genetically modified to be resistant to active ingredients such as herbicides, or to produce biologically active compounds that control infestation by plant pests.

Generally, a compound of formula (Ic) is used in the form of a composition (e.g. formulation) containing a carrier. A compound as of formula (Ic) and compositions thereof can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ulv) liquid, ultra low volume (ulv) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder.

A formulation typically comprises a liquid or solid carrier and optionally one or more customary formulaton auxiliaries, which may be solid or liquid auxiliaries, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactant, binders and/or tackifiers. The composition may also further comprise a fertilizer, a micronutrient donor or other preparations which influence the growth of plants as well as comprising a combination containing the compound of the invention with one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides.

The compositions are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid compound of the present invention and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the compound of the present invention with the auxiliary (auxiliaries). In the case of solid compounds of the invention, the grinding/milling of the compounds is to ensure specific particle size.

Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise - at least - a compound of formula (Ic) and the type of composition is to be selected to suit the intended aims and the prevailing circumstances.

As a rule, the compositions comprise <NUM> to <NUM>%, especially <NUM> to <NUM>%, of formula (Ic) and <NUM> to <NUM>%, especially <NUM> to <NUM>%, of at least one solid or liquid carrier, it being possible as a rule for <NUM> to <NUM>%, especially <NUM> to <NUM>%, of the composition to be surfactants (% in each case meaning percent by weight). Whereas concentrated compositions tend to be preferred for commercial goods, the end consumer as a rule uses dilute compositions which have substantially lower concentrations of active ingredient.

Examples of foliar formulation types for pre-mix compositions are:.

Whereas, examples of seed treatment formulation types for pre-mix compositions are:.

Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts.

As with the nature of the formulations, the methods of application, such as foliar, drench, spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

The tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries.

Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily employed in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

Generally, a tank-mix formulation for foliar or soil application comprises <NUM> to <NUM>%, especially <NUM> to <NUM> %, of the desired ingredients, and <NUM> to <NUM> %, especially <NUM> to <NUM> %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of <NUM> to <NUM> %, especially <NUM> to <NUM> %, based on the tank-mix formulation.

Typically, a pre-mix formulation for foliar application comprises <NUM> to <NUM> %, especially <NUM> to <NUM> %, of the desired ingredients, and <NUM> to <NUM> %, especially <NUM> to <NUM> %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of <NUM> to <NUM> %, especially <NUM> to <NUM> %, based on the pre-mix formulation.

Normally, a tank-mix formulation for seed treatment application comprises <NUM> to <NUM>%, especially <NUM> to <NUM> %, of the desired ingredients, and <NUM> to <NUM> %, especially <NUM> to <NUM> %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of <NUM> to <NUM> %, especially <NUM> to <NUM> %, based on the tank-mix formulation.

Typically, a pre-mix formulation for seed treatment application comprises <NUM> to <NUM> %, especially <NUM> to <NUM> %, of the desired ingredients, and <NUM> to <NUM> %, especially <NUM> to <NUM> %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of <NUM> to <NUM> %, especially <NUM> to <NUM> %, based on the pre-mix formulation.

Whereas commercial products will preferably be formulated as concentrates (e.g., pre-mix composition (formulation)), the end user will normally employ dilute formulations (e.g., tank mix composition).

Preferred seed treatment pre-mix formulations are aqueous suspension concentrates. The formulation can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful. The seeds may be presized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art. The compounds of the present invention are particularly suited for use in soil and seed treatment applications.

In general, the pre-mix compositions of the invention contain <NUM> to <NUM> especially <NUM> to <NUM>, advantageously <NUM> to <NUM> , % by mass of the desired ingredients, and <NUM> to <NUM>, especially <NUM> to <NUM>, % by mass of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries (or adjuvant) can be a surfactant in an amount of <NUM> to <NUM>, especially <NUM> to <NUM>, % by mass based on the mass of the pre-mix formulation.

The invention will now be illustrated by the following examples. Any treatments using a "Compound <NUM>" are examples according to the invention. Treatments using a "Compound <NUM>", "Compound <NUM>", or "Compound <NUM>" are comparative examples.

<NUM>-week old tomato plants cv. Roter Gnom are sprayed in a spray chamber with the formulated test compound diluted in water. The test plants are inoculated by spraying them with a spore suspension two days after application. The inoculated test plants are incubated at <NUM> and <NUM>% relative humidity in a greenhouse and the percentage leaf area covered by disease is assessed when an appropriate level of disease appears on untreated check plants (<NUM> - <NUM> days after application).

<NUM>-week old tomato plants cv. Roter Gnom are sprayed in a spray chamber with the formulated test compound diluted in water. The test plants are inoculated by spraying them with a spore suspension two days after application. The inoculated test plants are incubated at <NUM>/<NUM> (day/night) and <NUM>% relative humidity in a greenhouse and the percentage leaf area covered by disease is assessed when an appropriate level of disease appears on untreated check plants (<NUM> - <NUM> days after application).

A potato field trial was carried out in Tompkins, New York, USA in <NUM> to evaluate the efficacy of different compounds against early blight disease caused by Alternaria solani.

The potato tubers were applied in-furrow at planting by using boom sprayer with a flat fan nozzle. The disease occurred beginning of August and an assessment on disease severity and was done September 5th <NUM>.

Pest severity, <NUM> days after planting.

Compound <NUM> showed very good activity against Alternaria solani in potato at a rate of <NUM> Al/ha and higher, with an efficacy greater than <NUM>%. Compound <NUM> performed well but was clearly weaker than compound <NUM>. Both compounds provided disease control over a duration of <NUM> days after planting.

A tomato greenhouse trial was carried out in Sanlucar de Barrameda, Cadiz, Spain in <NUM> to evaluate the efficacy of different compounds against Fusarium oxysporum in tomato.

Three week old tomato plants were transplanted on April 7th <NUM> and the afterwards drench applied with the compounds using a water volume of <NUM> per plant.

In order to increase the disease pressure <NUM> Fusarium oxysporum suspension with a concentration of <NUM>'<NUM>'<NUM> spores per milliliter of water was drenched directly in the planting hole were the plants will be transplanted the next day. The assessment on disease incidence and was done <NUM> days after transplanting on August 17th <NUM>.

Pest incidence, <NUM> days after planting.

Compound <NUM> showed excellent efficacy against Fusarium oxysporum with <NUM>% control at a rate of <NUM> Al per hectare. Compound <NUM> protected the plant from Fusarium attack up to <NUM> days after transplanting. Compound <NUM> was weaker with <NUM>% control followed by compound <NUM> with an efficacy of <NUM>% and compound <NUM> with only <NUM>% control at much higher application rates.

An okra field trial was carried out in Kuppanur, Coimbatore, India in <NUM> to evaluate the efficacy of different compounds against Fusarium oxysporum in okra.

The okra seeds were planted on June 29th <NUM> and directly afterwards drench applied with the compounds using a water volume of <NUM> per plant. The disease occurred two weeks after planting and an assessment on disease incidence and was done August 28th <NUM>.

Crops and targets occurred in the trial:.

Compound <NUM> showed excellent efficacy against Fusarium oxysporum at a rate of <NUM> and <NUM> Al/ha, with an efficacy of <NUM>% and <NUM>%, respectively. The <NUM> Al/ha rate of compound <NUM> provided almost full disease control over a duration of <NUM> days after planting. Compound <NUM> performed well at a rate of <NUM>/ Al ha, but was clearly weaker than compound <NUM> applied at <NUM> Al/ha.

A melon greenhouse trial was carried out in El Ejido, Almeria, Spain in <NUM> to evaluate the efficacy of different compounds against Fusarium oxysporum in melon.

The melon transplants were planted on May 5th <NUM> and the afterwards drench applied with the compounds using a water volume of <NUM> per plant.

In order to increase the disease pressure each plot has been inoculated with <NUM> Fusarium oxysporum suspension with a concentration of <NUM>'<NUM> spores per millilitre of water three days before transplanting. The first disease symptoms were visible three weeks after transplanting and an assessment on disease severity and was done <NUM> days after transplanting on July 13th <NUM>.

Claim 1:
A method of controlling or preventing infestation of okra, melon, tomato and potato plants by phytopathogenic microorganisms selected from Sphaerotheca fuliginea, Leveillula taurica, Sclerotinia sclerotiorum, Cercospora, Fusarium oxysporum, Fusarium solani, Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Phytophthora infestans, Verticillium dahlia, Didymella bryoniae, Botrytis cinerea and Alternaria solani, comprising applying to a crop of plants, the locus thereof, or propagation material thereof, a compound of formula (Ic)
<CHM>
wherein
R11 and R12 are independently selected from halogen;
A is pyridyl which is substituted by one or two substituents independently selected from halogen, C<NUM>-C<NUM>-alkyl and C<NUM>-C<NUM>-haloalkyl.