Methods for controlling or preventing infestation of plants by a phytopathogenic microorganism of the genus pseudopyrenochaeta

Abstract

The present invention relates to methods for controlling or preventing infestation of plants by a phytopathogenic microorganism of the genus Pseudopyrenochaeta, comprising applying to a crop of plants, the locus thereof, or propagation material thereof, the compound of formula (I) or a pesticidal composition comprising the compound.

Description

[0001] PAT-111643-FF

[0002] 1

[0003] Title

[0004] Methods for controlling or preventing infestation of plants by a phytopathogenic microorganism of the genus Pseudopyrenochaeta

[0005] Technical Field

[0006] The present invention relates to methods for controlling or preventing infestation of plants by the phytopathogenic microorganism of the genus Pseudopyrenochaeta.

[0007] Background

[0008] Tomato (Solanum lycopersicum) is one of the most widely cultivated and economically important vegetable crops worldwide. However, tomato production is often threatened by various plant diseases, including root rot, which can cause significant yield losses and economic damage.

[0009] Tomato root rot is a devastating disease caused by soil-borne fungal pathogens. These fungi can infect the roots of tomato plants, leading to root decay, wilting, stunted growth, and ultimately plant death. Pseudopyrenochaeta lycopersici and Fusarium oxysporum are two primary fungal pathogens that causes a disease commonly known as root rot in tomatoes.

[0010] In root rot diseases, there is a subcategory called corky root rot disease, which is caused by Pseudopyrenochaeta lycopersici. This pathogen can attact tomato root system, causes rooting of feeder roots, brown lesions and typical corky root on main larger roots, As the infection advances, the roots harden and become brittle, impairing the plant’s ability to absorb water and nutrients, which in turn stunts growth and can lead to the death of the plant.

[0011] The control and prevention of tomato corky root rot are of utmost importance to ensure sustainable and profitable tomato production. The current invention is directed to fulfilling this need by providing novel methods for controlling or preventing infestation by Pseudopyrenochaeta lycopersici, thereby safeguarding staple crops from one of their most pernicious threats

[0012] Description of the embodiments

[0013] Cyclobutylcarboxamide compounds of formula (I) and processes for their preparation have been disclosed in WO2013 / 143811 and WO2015 / 003951 . PAT-111643-FF

[0014] 2

[0015] One cyclobutylcarboxamide, cyclobutrifluram (ISO name, CAS RN [1460292-16-3]), has been recently published as being under development as a nematicide (http: / / pmonline.azurewebsites.net / _Main / Pesticide.aspx). The chemical structure of cyclobutrifluram is the compound of formula (1-1), i.e., Compound 1 of the present application.

[0016] It was known that the compound of formula (I) (e.g., cyclobutrifluram) has activity against root-knot nematodes such as Meloidogyne genus and cyst-forming nematodes such as Heterodera genus. These nematode species are soil based and attack the root system of many plants. However, no data has been reported that the compound of formula (I) (e.g., cyclobutrifluram) has any fungicial activity against a fungi from the genus Pseudopyrenochaeta, or on tomato, and in particular no data has been reported that the compound of formula (I) (e.g., cyclobutrifluram) has any activity against Pseudopyrenochaeta lycopersici.

[0017] It has now been surprisingly found that the cyclobutylcarboxamide compound of formula (I) (e.g., cyclobutrifluram) is highly effective at controlling or preventing the infestation of plants by a phytopathogenic microorganism of the genus Pseudopyrenochaeta. This highly effective compound thus represents an important new solution for farmers to control or prevent infestation of plants by a phytopathogenic microorganism of the genus Pseudopyrenochaeta. It has been found that the compound of formula (I) (e.g., cyclobutrifluram) is highly effective when applied to the growth substrate (e.g., soil) of tomato against the infestation by a phytopathogenic microorganism of the genus Pseudopyrenochaeta. Testing has shown the compound of formula (I) (e.g., cyclobutrifluram) protects the plants far more effectively than any currently used commercial standards. Thus, the compound of formula (I) (e.g., cyclobutrifluram) presents an excellent tool for farmers for controlling or preventing infestation of plants by a phytopathogenic microorganism of the genus Pseudopyrenochaeta.

[0018] Hence, as embodiment 1 , there is provided a method for controlling or preventing infestation of plants by a phytopathogenic microorganism of the genus Pseudopyrenochaeta, comprising applying to a crop of plants, the locus thereof, or propagation material thereof, the compound of formula (I) PAT-111643-FF

[0019] 3 wherein

[0020] R11 and R12 are independently selected from halogen;

[0021] A is pyridyl which is substituted by one or two substituents independently selected from halogen, C1- C4-alkyl and Ci-C4-haloalkyl.

[0022] In a preferred embodiment, Rn and R12 are independently selected from chloro and fluoro; and

[0023] A is pyrid-2-yl or pyrid-3-yl, which is substituted by one or two substituents independently selected from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl.

[0024] In a more preferred embodiment, A is selected from

[0025] R13 is halogen, Ci-C4-alkyl or Ci-C4-haloalkyl.

[0026] In an even more preferred embodiment, the compound is selected from any one of Compound 1 to

[0027] Compound 7 of formula (I) wherein Rn, R12 and A are as defined in the following table: PAT-111643-FF

[0028] 4

[0029] In the most preferred embodiment, the compound is Compound 1 ,.

[0030] The compound of formula (I) represents the compound in cis configuration: the phenyl ring on the left hand side and the pyridyl-C(=O)-NH group on the right hand side are cis to each other on the cyclobutyl ring as illustrated for compound of formula (la) and (lb):

[0031] Particularly, Cyclobutrifluram as disclosed above represents the compound in cis configuration: the phenyl ring on the left hand side and the pyridyl-C(=O)-NH group on the right hand side are cis to each other on the cyclobutyl ring as illustrated for compound of formula (1-1 a) and (1-1 b):

[0032] The wedged bonds shown in the compounds of formula (la), (lb), (1-1 a) and (1-1 b) represent absolute stereochemistry, whereas the thick straight bonds such as those shown for compound of formula (I) and (1-1) represent relative stereochemistry.

[0033] It has also surprisingly been found that one enantiomer of the compound of formula (I) (e.g., cyclobutrifluram) is particularly useful in a method for controlling or preventing infestation of plants by a phytopathogenic microorganism of the genus Pseudopyrenochaeta.

[0034] Thus, as embodiment 2, there is provided the method according to embodiment 1 wherein the compound of formula (I) (e.g., cyclobutrifluram) is in the form of the (1 S, 2S) stereoisomer, in which PAT-111643-FF

[0035] 5 case the compound of formula (I) would have the structure of formula (la), and cyclobutrifluram would have the structure of formula (1-1 a):

[0036] In a method according to embodiment 3, the compound comprises both the (1 S,2S) and (1 R,2R) stereoisomers, the ratio of the (1 S,2S) stereoisomer to its enantiomer (1 R,2R) is greater than 1 :1. Preferably, the ratio of the (1 S,2S) to (1 R,2R) is greater than 1.5:1 , more preferably greater than 2.5:1 , especially greater than 4:1 , advantageously greater than 9:1 , desirably greater than 20:1 , in particular greater than 35:1 .

[0037] A skilled person is aware that according to the method of embodiments 1 to 3, the compound of formula (I) (e.g., cyclobutrifluram) is generally applied as part of a pesticidal composition. Hence, as embodiment 4, there is provided a method for controlling or preventing infestation of plants by a phytopathogenic microorganism of the genus Pseudopyrenochaeta comprising applying to a crop of plants, the locus thereof, or propagation material thereof a pesticidal composition comprising the compound of formula (I) (e.g., cyclobutrifluram) and one or more formulation adjuvants.

[0038] As embodiment 5, there is provided a method for controlling or preventing infestation of plants by a phytopathogenic microorganism of the genus Pseudopyrenochaeta comprising applying to a crop of plants, the locus thereof, or propagation material thereof a pesticidal composition comprising a compound of formula (la) (e.g., a compound of formula (1-1 a)) and one or more formulation adjuvants.

[0039] As embodiment 6, there is provided the method according to any one of embodiments 1 to 5, wherein the pesticidal composition is a suspension composition.

[0040] As embodiment 7, there is provided the method according to any one of embodiments 1 to 6 comprising the compound of formula (I) (e.g., cyclobutrifluram) or a pesticidal composition comprising the compound is applied to the growth substrate of the crop of plant; preferably, the growth substrate is soil.

[0041] As embodiment 8, there is provided the method according to any one of embodiments 1 to 7, wherein the compound of formula (I) (e.g., cyclobutrifluram) or a pesticidal composition comprising the compound is applied by drip, drenching or injection ; preferably by drenching comprising the steps. PAT-111643-FF

[0042] 6

[0043] Such applications to a growth substratell are well-known to the person skilled in the art. Additionally, application may be to a hydroponic growth medium.

[0044] As embodiment 9, there is provided the use of the compound of formula (I) (e.g., cyclobutrifluram) or a pesticidal composition comprising the compound as defined in any one of embodiments 1 to 6 for controlling or preventing infestation of plants by a phytopathogenic microorganism of the genus Pseudopyrenochaeta.

[0045] As embodiment 10, there is provided a method for growing a plant comprising applying or treating a propagation material thereof with the compound of formula (I) (e.g., cyclobutrifluram) or a pesticidal composition comprising the compound as defined in any one of embodiments 1 to 6.

[0046] As embodiment 11 , there is provided a method or use according to any one of embodiments 1 to 10 wherein the compound of formula (I) (e.g., cyclobutrifluram) or a pesticidal composition comprising the compound is applied to the growth substrate of the crop of plant; preferably, the growth substrate is soil, or directly to the root of the plant.

[0047] As embodiment 12, there is provided a method or use according to any one of embodiments 1 to 11 , wherein the compound of formula (I) (e.g., cyclobutrifluram) or a pesticidal composition comprising the compound is applied within 15 days after transplanting seedlings of the plants; preferably, within 7 days after transplanting seedlings of the plants; more preferably, within 3 days after transplanting seedlings of the plants; most preferably, on the day of transplantation.

[0048] As embodiment 13, there is provided a method or use according to any one of embodiments 1 to 12, wherein the compound of formula (I) (e.g., cyclobutrifluram) is applied at a rate of 5-750 gai / ha, preferably, 15-500 gai / ha, more preferably, 30-250 gai / ha.

[0049] As embodiment 14, there is provided a method or use according to any one of embodiments 1 to 13, wherein the phytopathogenic microorganism is Pseudopyrenochaeta lycopersici.

[0050] As embodiment 15, there is provided a method or use according to any one of embodiments 1 to 14, wherein the plant is tomato.

[0051] As embodiment 16, there is provided a method for controlling or preventing infestation of tomato plants by root rot, comprising applying to a crop of tomato plants, the locus thereof, or propagation material thereof, the compound of formula (I), e.g. cyclobutrifluram, or a pesticidal composition comprising the compound. In some embodiments, the method is for controlling or preventing infestation of tomato plants by corky root rot. PAT-111643-FF

[0052] 7

[0053] The preparation of the compound of formula (I) (e.g., cyclobutrifluram) has been disclosed in WO2013 / 143811 and WO2015 / 003951 which are incorporated herein by reference.

[0054] The term “seed” embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corns, bulbs, fruit, tubers, grains, rhizomes, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.

[0055] Application according to the methods or uses according to any one of embodiments 1 to 16 is preferably to a crop of plants, the locus thereof or propagation material thereof. Preferably application is to a crop of plants or propagation material thereof, e.g., leaves of the crop. Application of the compound of formula (I) (e.g., cyclobutrifluram) or a pesticidal composition comprising the compound can be performed according to any of the usual modes of application, e.g. foliar, drench, soil, in furrow etc, preferably through soil.

[0056] The methods or uses as defined in any one of embodiments 1 to 16 are suitable for use on any 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.

[0057] Generally, the compound of formula (I) (e.g., cyclobutrifluram) is used in the form of a composition (e.g. formulation) containing a carrier. The compound of formula (I) (e.g., Cyclobutrifluram) and compositions comprising the compound as defined in any one of embodiments 1 to 16 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.

[0058] A formulation typically comprises a liquid or solid carrier and optionally one or more customary formulation 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. PAT-111643-FF

[0059] 8

[0060] 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.

[0061] 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 - the compound of formula (I) (e.g., cyclobutrifluram) and the type of composition is to be selected to suit the intended aims and the prevailing circumstances.

[0062] As a rule, the compositions comprise 0.1 to 99%, especially 0.1 to 95%, of the compound of formula (I) (e.g., cyclobutrifluram) and 1 to 99.9%, especially 5 to 99.9%, of at least one solid or liquid carrier, it being possible as a rule for 0 to 25%, especially 0.1 to 20%, 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.

[0063] Examples of foliar formulation types for pre-mix compositions are: GR: Granules

[0064] WP: wettable powders

[0065] WG: water dispersable granules (powders)

[0066] SG: water soluble granules

[0067] SL: soluble concentrates

[0068] EC: emulsifiable concentrate

[0069] EW: emulsions, oil in water

[0070] ME: micro-emulsion

[0071] SC: aqueous suspension concentrate

[0072] CS: aqueous capsule suspension

[0073] CD: oil-based suspension concentrate, and SE: aqueous suspo-emulsion.

[0074] Whereas, examples of seed treatment formulation types for pre-mix compositions are: WS: wettable powders for seed treatment slurry LS: solution for seed treatment ES: emulsions for seed treatment

[0075] FS: suspension concentrate for seed treatment

[0076] WG: water dispersible granules, and PAT-111643-FF

[0077] 9

[0078] CS: aqueous capsule suspension.

[0079] Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] Generally, a tank-mix formulation for foliar or soil application comprises 0.1 to 20%, especially 0.1 to 15 %, of the desired ingredients, and 99.9 to 80 %, especially 99.9 to 85 %, 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 0 to 20 %, especially 0.1 to 15 %, based on the tank-mix formulation.

[0084] Typically, a pre-mix formulation for foliar application comprises 0.1 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.9 to 0.1 %, especially 99 to 5 %, 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 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.

[0085] Normally, a tank-mix formulation for seed treatment application comprises 0.25 to 80 %, especially 1 to 75 %, of the desired ingredients, and 99.75 to 20 %, especially 99 to 25 %, 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 0 to 40 %, especially 0.5 to 30 %, based on the tank-mix formulation.

[0086] Typically, a pre-mix formulation for seed treatment application comprises 0.5 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.5 to 0.1 %, especially 99 to 5 %, 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 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.

[0087] 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). PAT-111643-FF

[0088] 10

[0089] 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 compound of formula (I) (e.g., Cyclobutrifluram) is particularly suited for use in soil and seed treatment applications.

[0090] The invention will now be illustrated by the following non-limiting Examples. All citations are incorporated by reference.

[0091] BIOLOGICAL EXAMPLES

[0092] Example 1 In-vitro activity of Compound 1 against of P. lycopersici and F. oxysporum

[0093] P. lycopersici (PL) isolate (23#72-5-1-1) and F. oxysporium (FO) isolate (FSP0043), which were isolated from tomato root samples, were subjected to a mycelial growth-inhibition assay. The fungicidal activities of Compound 1 and Fluopyram were tested on Petri dishes using a potato- dextrose-agar (PDA) medium.

[0094] Compound 1 was diluted in dimethyl sulfoxide to obtain stock solution of 10,000 mg L-1and Commercial SDHI standard Fluopyram (Velum, 41.7% of fluopyram, A.L, Bayer) was diluted in water to obtain stock solution of 10,000 mg L1. Both solutions were subjected to serial dilution to obtain the concentrations from 100 mg L1to 0.001 mg L1

[0095] A 5 mm mycelial plug from each isolate was inverted and transferred to sterile 90 x 15 mm Petri dishes, with three replicates per fungicide concentration. The cultures were incubated at 25 ± 1 °C in darkness, with incubation periods of 14 days for PL and 7 days for FO. Following incubation, the diameters of the mycelial colonies were measured. Inhibition rates were calculated and EC50 values were determined using a regression line fitted to the log-transformed percentage inhibition plotted against the log-transformed fungicide concentration.

[0096] Table 1. EC50 values of Compound 1 and Fluopyram against P. lycopersici and F. oxysporum,

[0097] Compound 1 Fluopyram

[0098] EC50 (mg / L) EC50 (mg / L)

[0099] Pseudopyrenochaeta lycopersici 0.0492 1 .6404

[0100] Fusarium oxysporum 0.9745 301 .695

[0101] The results show that surprisingly Compound 1 exhibits a significantly higher in-vitro activity against P. lycopersici and F. oxysporum, compared to Fluopyram. PAT-111643-FF

[0102] 11

[0103] Example 2 Pot trial results of Compound 1 against tomoato root rot caused by P. lycopersici and F. Oxysporium

[0104] Pseudopyrenochaeta lycopersici and Fusarium oxysporum isolates were incubated in potato-dextrose (PD) culture medium at 25 °C for 15 days. The cultures were then stirred with a tissue crusher and diluted 5-fold for use as inoculum. Tomato seedlings were cultured in a greenhouse at 18-28°C until the 4-true-leaf stage for use in inoculation experiments.

[0105] Root sinking and soil infection methods were used for root inoculation. Tomato roots were wounded and dipped in the pathogen solution for 5 minutes and then transplanted into 10*10 pots with 50ml of pathogen inoculation solution in each pot. Ten plants were inoculated for each pathogen isolate, and water-treated plants served as controls. The inoculated seedlings were incubated at 18-25°C with a 12-hour light / day photoperiod for 30 days.

[0106] Compound 1 450SC and Fluopyram 500SC were applied to the soil by drench and water was applied as check. The seedlings were incubated at temperatures ranging from 18-25°C with a 12-hour light cycle per day for 30 days. Post incubation, the disease severity was recorded, based on the percentage of root infection.

[0107] The control rate was calculated using the formula:

[0108] Disease control rate (%) = (disease severity of check - disease severity of treatment) / disease severity of check * 100%

[0109] Table 2. Pot trial results of Compound 1 against tomoato root rot caused by P. lycopersici and F. oxysporium PAT-111643-FF

[0110] 12

[0111] The results above demonstrate that surprisingly Compound 1 offers significantly better control against tomato root rot compared with commercial SDHI standard Fluopyram, even though the latter was at a higher dose.

Claims

PAT-111643-FF13Claims1 . A method for controlling or preventing infestation of plants by a phytopathogenic microorganism of the genus Pseudopyrenochaeta, comprising applying to a crop of plants, the locus thereof, or propagation material thereof, the compound of formula (I)whereinR11 and R12 are independently selected from halogen;A is pyridyl which is substituted by one or two substituents independently selected from halogen, C1- C4-alkyl and Ci-C4-haloalkyl.

2. The method according to claim 1 , whereinR11 and R12 are independently selected from chloro and fluoro;A is pyrid-2-yl or pyrid-3-yl, which is substituted by one or two substituents independently selected from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl.

3. The method according to claim 1 or 2 whereinA is selected fromR13 is halogen, Ci-C4-alkyl or Ci-C4-haloalkyl.

4. The method according to any one of claims 1 to 3, wherein the compound is selected from any one of Compound 1 to Compound 7 of formula (I)PAT-111643-FF14wherein Rn, R12 and A are as defined in the following table:

5. The method according to claim 4, wherein the compound is Compound 1 .

6. The method according to any one of claims 1 to 5, wherein the compound comprises (1 S,2S) and (1 R,2R) stereoisomers, the ratio of the (1 S,2S) stereoisomer to its enantiomer (1 R,2R) is greater than 4:1 , preferably greater than 9:1.

7. The method according to any one of claims 1 to 6, wherein the compound is applied as a pesticidal composition comprising the compound and one or more formulation adjuvants; preferably, the pesticidal composition is a suspension composition.

8. The method according to any one of claims 1 to 7, wherein the compound or a pesticidal composition comprising the compound or the pesticidal composition comprising the compound is applied to the growth substrate of the crop of plant; preferably, the growth substrate is soil.

9. The method according to any one of claims 1 to 8, wherein the compound or the pesticidal composition comprising the compound is applied by drip, drenching or injection ; preferably by drenching.

10. The method according to any one of claims 1 to 9, wherein the compound or a pesticidal composition comprising the compound is applied within 15 days after transplanting seedlings of the plants; preferably on the day of transplantation.PAT-111643-FF1511. The method according to any one of claims 1 to 10, wherein the compound is applied at a rate of 5-750 gai / ha, preferably, 15-500 gai / ha, more preferably, 30-250 gai / ha.

12. Use of the compound as defined in any one of claims 1 to 6 or a pesticidal composition comprising the compound for controlling or preventing infestation of plants by a phytopathogenic microorganism of the genus Pseudopyrenochaeta.

13. The method or use according to any one of claims 1 to 12, wherein the phytopathogenic microorganism is Pseudopyrenochaeta lycopersici.

14. The method or use according to any one of claims 1 to 13, wherein the plant is tomato.

15. A method for controlling or preventing infestation of tomato plants by root rot, especially by corky root rot, comprising applying to a crop of tomato plants, the locus thereof, or propagation material thereof, the compound as defined in any one of claims 1 to 6 or a pesticidal composition comprising the compound.

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