Fungicidal treatment for panicle diseases in rice using n-methoxy(phenylethyl)-pyrazole carboxamides

Abstract

The present invention relates to the use of N-methoxy(phenylethyl)-pyrazole carboxamides for the control of phytopathogenic diseases of useful plants, especially phytopathogenic fungi, and to a method of controlling such diseases, and / or fungi, on useful plants. In particular, the present invention relates to the use of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro- phenyl)ethyl]-1H-pyrazole-4-carboxamide (pydiflumetofen) for the control of Bipolaris oryzae, Curvularia lunata, Fusarium equiseti, Fusarium graminearum, Alternaria alternata and / or Sarocladium oryzae as causative agents for dirty panicle disease (DPD) on rice plants.

Description

[0001] FUNGICIDAL TREATMENT FOR PANICLE DISEASES IN RICE USING N- METHOXY(PHENYLETHYL)-PYRAZOLE CARBOXAMIDES

[0002] FIELD OF THE INVENTION

[0003] The present invention relates to the use of N-methoxy(phenylethyl)-pyrazole carboxamides for the control of phytopathogenic diseases of useful plants, especially phytopathogenic fungi, and to a method of controlling such diseases, and / or fungi, on useful plants. In particular, the present invention relates to the use of 3-(difluoromethyl)-W-methoxy-1 -methyl-W-[1 -methyl-2-(2,4,6-trichloro- phenyl)ethyl]-1 H-pyrazole-4-carboxamide (pydiflumetofen) for the prevention and / or control of panicle diseases of rice, in particular dirty panicle disease (DPD), also known as spikelet rot disease (SRD).

[0004] BACKGROUND OF THE INVENTION

[0005] Panicle diseases of rice have generally received comparatively little attention. False smut (Ustilaginoidea virens), kernel smut (Tilletia bardayana), and scab (Fusarium graminearum, other Fusarium species being also considered as saprophytes), have long been considered minor rice diseases that do not warrant specific control measures. The prevention of grain discoloration (associated with a wide range of organisms) has been generally associated to better pre- and postharvest measures; while many fungi found on glumes and panicles have commonly been seen as organisms that are only found on weakened plants or moribund tissues. The widespread cultivation of rice plant varieties with different panicle morphologies in cropping systems, partly due to their photoperiod-insensitivity and having high yield potential, has led to a significant increase in the impact of such diseases in rice production.

[0006] Dirty panicle disease (DPD, also known as rice spikelet rot (SRD)) is caused by several fungal phytopathogens, namely Bipolaris oryzae, Curvularia lunata, Fusarium equiseti, Fusarium graminearum, Alternaria alternata and Sarocladium oryzae, which result in damage and depreciation of rice seeds.

[0007] Dirty panicle disease (DPD) may arise in particular in the productive stage of rice, but more often during post-harvest storage. Unhealthy rice seeds with dirty panicle disease are potent reservoirs of pathogens meaning they are unable to be used as seed stock as they can spread the disease in the paddy fields leading to severe loss of rice yield and quality. Unhealthy rice seeds with dirty panicle disease can transmit the disease during storage, and hence infected grains cannot be stored in contact with uninfected seeds, nor marketed, since the quality of rice grains determines the commercial value of this cereal product. Accordingly, rice grains that show abnormal coloration and / or lesions in line with DPD must be sorted out.

[0008] The disease is characterized by the appearance of dirty-looking panicles due to the presence of bacterial exudates and discoloration. Symptoms of dirty panicle disease include the presence of brown to black lesions on panicles, often accompanied by a foul odour. This discoloration and reduced quality lead to economic losses for rice farmers since infected grains may at best be employed as animal feed, but normally require destruction as agricultural waste. To put this in perspective, since the early 2010s, massive losses have increasingly haunted the rice production in South East Asia, where DPD-causing fungal pests spread during storage, strongly reducing profits to the point of causing an economic crisis.

[0009] It is hard, however, to detect and prevent DPD early, as the physical symptoms, in particular grain discoloration, mainly occur on mature rice grains at the harvesting phase. When DPD occurs during rice production, it is often too late to recover the quality of affected rice yields. Also, improper storage of healthy-looking rice seeds can induce DPD since the pathogens are often present on rice grain surfaces.

[0010] Hence, in order to maintain the quality of seed stock before use in rice cultivation, seed treatment is often performed. Chemical treatment of rice seeds with pesticides may be an approach for rapid disease suppression. However, the pesticides used to date require increasing concentrations for an effective treatment. Also, since several different species of fungi may cause the disease, alone or in combination, often the pesticides lack the spectrum required to secure a suitable treatment.

[0011] Accordingly there is need for an improved seed or plant treatment, with a broad spectrum and high efficacy.

[0012] It is known from Chen Y. et al., Phytoparasitica, 2013, 41 , 277-284 that ergosterol biosynthesis inhibitor (EBI) fungicides, such as prochloraz, difenoconazole, propiconazole, and tebuconazole, are extensively used (especially in China), for the control of rice diseases, such as rice sheath blight, rice blast, and dirty panicle disease (DPD). 3-(Difluoromethyl)-W-methoxy-1 - methyl-A / -[1 -methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1 H-pyrazole-4-carboxamide (known by its common name ‘pydiflumetofen’) described in WO 2010 / 063700 is a broad-spectrum foliar fungicide and the first example of the new group of N-methoxy-(phenylethyl)-pyrazole-carboxamides within the succinate dehydrogenase inhibitor (SDHI) class.

[0013] The present invention is based on the surprising finding that pydiflumetofen exhibits a high level of activity against principally all of the fungal species known to date to cause dirty panicle disease (DPD) in rice plants.

[0014] Thus, in a first aspect the present invention relates to a method of controlling dirty panicle disease (DPD) on rice plants, said method comprising applying an effective amount of pydiflumetofen, to the plant, plant part, propagation material of the plant, or to the locus thereof.

[0015] In another aspect, there is provided a method of controlling dirty panicle disease (DPD) on rice plants, said method comprising applying an effective amount of a composition comprising pydiflumetofen to the plant, plant part, or locus thereof. In a further aspect, there is provided a use of pydiflumetofen, or an agrochemically acceptable salt, isomer, stereoisomer, diastereoisomer, enantiomer or tautomer thereof, to control dirty panicle disease (DPD).

[0016] Pydiflumetofen and its preparation are described in WO 2010 / 063700, WO 2013 / 127764, and WO 2014 / 206855. The skilled person will appreciate that 3-(difluoromethyl)-W-methoxy-1 - methyl-W-[1 -methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1 H-pyrazole-4-carboxamide exists in two enantiomeric forms: 3-(difluoromethyl)-W-methoxy-1 -methy I - A / -[( 1 R)-1 -methyl-2-(2,4,6-trichloro- pheny l)ethy I]- 1 / - / -pyrazole-4-carboxamide and 3-(difluoromethyl)-W-methoxy-1 -methy I- / -[( 1 S)-1 - methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1 / - / -pyrazole-4-carboxamide. Both enantiomers can be used for the control or suppression of phytopathogenic bacteria, individually, or as a racemate. The compound 3-(difluoromethyl)-W-methoxy-1 - methy I - A / -[1 -methy I -2-(2 ,4, 6-trich loro-pheny l)ethy I]- 1 H- pyrazole-4-carboxamide may be referred to herein by full name, ISO name, or as “the compound”.

[0017] The term “locus” as used herein means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.

[0018] The term “plants” refers to all physical parts of a plant, including seeds, seedlings, roots, stems, stalks and foliage.

[0019] The term “plant propagation material” as used herein is understood to denote generative parts of a useful plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as grains or seeds. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, corms, rhizomes, and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion in the compound. Preferably “plant propagation material” is understood to denote seeds, grains and / or roots, more preferably seeds.

[0020] The term “reproductive growth stage” refers to the final stage of plant growth which follows germination and vegetative growth. During the reproductive growth stage, the plant’s energy is directed to the production of flowers, fruits and seeds. Several growth stages help identify critical periods during the life cycle of the rice crop. They are generally separated into stages primarily associated either with vegetative or reproductive development. The vegetative phase occurs first and is associated with the six- to eight-week period following planting. The reproductive phase follows and is generally associated with the formation, development and maturation of the panicle and grain. Panicle initiation is the first stage in the reproductive phase of growth.

[0021] The reproductive growth stage typically starts at the beginning of stem elongation (BBCH 30). In rice, it includes panicle initiation (BBCH 30), panicle formation (BBCH 32), internode elongation (BBCH 34), spikelet differentiation (BBCH 35), meiosis (BBCH 39), booting (BBCH 41 - 49), and heading (BBCH 51 ), which indicates the beginning of panicle emergence. BBCH 43 is known as the mid-boot stage. At BBCH 58 about 80% of the panicle has emerged.

[0022] The developing panicle is microscopic in size inside the stem, and panicle initiation can usually be associated with the beginning of stem internode formation. As the internode elongation stage begins, a build-up of chlorophyll occurs between the nodes that are to separate in the process of forming the first stem internode between them. This accumulation of chlorophyll imparts a green colour that encircles the developing internode producing a green ring or band. Thus, the internode elongation stage is sometimes referred to as the green ring stage. This stage is also referred to as first green ring because additional internodes that form on top of the first internode can also have the green ring effect as they begin to form. A total of five internodes can be produced in the formation of a stem of rice. As internode and panicle formation continue, the panicle differentiation stage occurs. Panicle differentiation is the first stage in the reproductive phase when the newly forming panicle becomes visible. At this stage, the panicle inside the stem has grown to approximately 1 / 8 inch. In the metric system, the length is approximately 2 millimetres, and the stage is sometimes referred to as the 2 mm panicle stage. The panicle continues to grow and develop inside the stem. As it does, the growth stage is referred to as booting and identified by the length of the panicle. When the panicle is up to 2 inches in length, the growth stage is early boot. Middle boot and late boot occur when the length of the panicle is 2 to 5 inches and 5 inches or greater, respectively. Up to this point, identification of the growth stages in the reproductive phase requires the stem to be dissected (split in half). During late boot, the panicle develops completely, and the growth stages that follow occur after the panicle has exerted and is visible outside the stem. The heading stage is noted when a portion of a panicle is observed growing out of the end of a rice stem. From this time forward, growth stages are based on the state of the panicle outside of the rice stem. Heading stages are identified by percentages, and the 50 percent heading stage occurs when 50 percent of rice stems are heading or headed (panicle completely emerged from the stem).

[0023] In one embodiment, the crop plants are at a BBCH growth stage from 30 to 59 at the time of treatment. In a further embodiment, the crop plants are at a BBCH growth stage from 41 to 49 at the time of treatment. In a further embodiment, the crop plants are at a BBCH growth stage from 41 to 45 at the time of treatment. In a further embodiment, there is a single application of pydiflumetofen to the crop plants, and the crop plants are at a BBCH growth stage from 41 to 45, at the time of treatment, preferably, the crop plants are at BBCH growth stage 43 at the time of treatment. In a further embodiment, there are two applications of pydiflumetofen to the crop plants, and the first application of pydiflumetofen occurs when the crop plants are at a BBCH growth stage from 41 to 45 at the time of treatment, and the second application of pydiflumetofen occurs when the crop plants are at a BBCH growth stage from 55 to 59 at the time of treatment. Preferably, when there are two applications of pydiflumetofen to the crop plants, at the first application of pydiflumetofen the crop plants are at BBCH growth stage 43 at the time of treatment, and at the second application of pydiflumetofen the crop plants are at BBCH growth stage 58 at the time of treatment. In order to control dirty panicle disease (DPD), pydiflumetofen is applied or administered in an “effective amount”, by which is meant any amount of pydiflumetofen that, upon suitable application, is sufficient to achieve the desired level of control of dirty panicle disease (DPD).

[0024] Pydiflumetofen for the control of dirty panicle disease (DPD) can be used in unmodified form or, preferably, together with carriers and adjuvants conventionally employed in the art of formulation, and as described previously, for example, in WO 2010 / 063700. Typically, when used for fungal control, pydiflumetofen is applied to useful plants via foliar application. However, in order to control dirty panicle disease (DPD), the preferred application methods are directly to the plant, the locus of the plant (e.g. the soil) or directly to plant propagation material (e.g. applied to the seed).

[0025] In a further embodiment, pydiflumetofen is applied to the plant, plant part, or locus thereof in the form of a fungicidal formulation. This formulation may contain one or more other desirable components including but not limited to liquid diluents, binders to serve as a matrix for the compounds as described herein, fillers for protecting the seeds, and plasticizers to improve flexibility, adhesion and / or spreadability of the coating.

[0026] The fungicidal formulation e.g. a composition comprising pydiflumetofen, and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound, may be prepared in a known manner, typically by mixing and / or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).

[0027] Typical rates of application per hectare is generally 1 g to 2000 g of pydiflumetofen per hectare, in particular 10 g to 1000 g / ha, preferably 10 to 800 g / ha, more preferably 20 g to 600 g / ha, and most preferably 40 g to 500 g / ha. In particular, pydiflumetofen is applied at 40 g to 400 g of active ingredient per hectare. In one embodiment, pydiflumetofen is applied at 50 g to 100 g of active ingredient per hectare. In one embodiment, pydiflumetofen is applied at 60 g to 75 g of active ingredient per hectare. When used for treating seeds or as a drenching agent, convenient rates of application are from 1 mg to 50 g of active substance per kg of seeds, preferably from 10 mg to 30 g of active substance per kg of seeds, and more preferably, from 10 mg to 1 g of active substance per kg of seeds.

[0028] In a further embodiment, pydiflumetofen is applied once to the rice crop at a rate of 75 g of active ingredient per hectare. In another embodiment, pydiflumetofen is applied twice to the rice crop at a rate of 75 g of active ingredient per hectare.

[0029] In a further embodiment, pydiflumetofen is used in a foliar treatment composition or a seed treatment composition. This is particularly desirable where seeds or grains are to be employed as seed material, and not for animal or human consumption.

[0030] In a further embodiment, pydiflumetofen is used in a drenching treatment composition. The compositions of the invention may be employed in any conventional form, for example in the form of a twin pack, a powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EG), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0031] Such compositions may be produced in conventional manner, e.g., by mixing the active ingredients with appropriate formulation inerts (diluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects). Also conventional slow release formulations may be employed where long lasting efficacy is intended. Particularly formulations to be applied in spraying forms, such as water dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EG and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvancy effects, e.g. the condensation product of formaldehyde with naphthalene sulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkyl sulphate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

[0032] In general, the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% solid or liquid formulation inerts and adjuvant(s), the active agent consisting of at least containing pydiflumetofen together with component (B) and (C), and optionally other active agents, particularly microbiocides or conservatives or the like. Concentrated forms of compositions generally contain in between about 2 and 80%, preferably between about 5 and 70% by weight of active agent. Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.

[0033] Pydiflumetofen may be the sole active ingredient of a composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate. An additional active ingredient may, in some cases, result in unexpected synergistic activities.

[0034] Examples of suitable additional active ingredients include a compound selected from the group of substances consisting of (4E,10Z)-tetradeca-4, 10-dienyl acetate, (7E,9Z)-dodeca-7,9-dien-1 -yl acetate, (E)-6-methylhept-2-en-4-ol, (E)-dec-5-en-1 -yl acetate with (E)-dec-5-en-1 -ol, (E)-tridec-4- en-1 -yl acetate, (S)-bioallethrin, (Z)-dodec-7-en-1 -yl acetate, (Z)-hexadec-11 -en-1 -yl acetate, (Z)- hexadec-11 -enal, (Z)-hexadec-13-en-11 -yn-1 -yl acetate, (Z)-icos-13-en-10-one, (Z)-tetradec-7-en- 1 -al, (Z)-tetradec-9-en-1 -ol, (Z)-tetradec-9-en-1 -yl acetate, 1 ,1 -bis(4-chlorophenyl)-2-ethoxyethanol, 1 -(2-chlorophenyl)-3,3-dimethyl-2-(1 ,2 ,4-triazol - 1 -ylmethyl)butan-2-ol, 1 -(5-bromo-2-pyridyl)-2-(2,4- dif I uoropheny I)- 1 ,1 -dif I u oro-3-( 1 ,2 ,4-triazol- 1 -yl)propan-2-ol, 1 -hydroxy-1 H-pyridine-2-thione, 1 - methylcyclopropene, 1 -naphthaleneacetamide, 1 -naphthylacetic acid, 2,2-dichlorovinyl 2- ethylsulfinylethyl methyl phosphate, 2,4-D, 2,4-DB, 2,6-dichloro-N-(4- trifluormethylbenzyl)benzamide, 2-(1 ,3-dithiolan-2-yl)phenyl dimpetrethylcarbamate, 2-(2- butoxyethoxy)ethyl piperonylate, 2-(4,5-dimethyl-1 ,3-dioxolan-2-yl)phenyl methylcarbamate, 2- (difluoromethyl)-N-((3R)-1 ,1 ,3-trimethylindan-4-yl) pyridine-3-carboxamide, 2-(octylthio)-ethanol, 2- bromo-2-bromomethyl-pentanedinitrile, 2-chlorovinyl diethyl phosphate, 2-imidazolidone, 2- methyl(prop-2-ynyl)aminophenyl methylcarbamate, 2-thiocyanatoethyl laurate, 3-(4-chlorophenyl)-5- methylrhodanine, 3-(difluoromethyl)-1 -methyl-N-[1 ,1 ,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 3-(difluoromethyl)-N-(7-fluoro-1 ,1 ,3,3-tetramethyl-indan-4-yl)-1 -methyl-pyrazole-4-carboxamide, 3- (difluoromethyl)-N-(7-fluoro-1 ,1 ,3,3-tetramethyl-indan-4-yl)-1 -methyl-pyrazole-4-carboxamide, 3- chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine, 3-methyl-1 -phenylpyrazol-5-yl dimethyl-carbamate, 3-phenylphenol, 4,5-dichlorodithiol-3-one, 4-(2,6-difluorophenyl)-6-methyl-5- phenyl-pyridazine-3-carbonitrile, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5- dimethyl-pyrazol-3-amine, 4-(quinoxalin-2-ylamino)benzenesulfonamide, 4-[[6-[2-(2,4- difluorophenyl)-1 ,1 -difluoro-2-hydroxy-3-(1 ,2,4-triazol-1 -yl)propyl]-3-pyridyl]oxy]benzonitrile, 4- chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, 4-CPA, 4- methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate, 4-methylnonan-5-ol with 4-methylnonan-5- one, 4-phenylphenol, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, 5-amino-1 ,3,4-thiadiazole- 2-thiol, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine, 5-hydroxy-6-methyl-4-(((E)-pyridin-3- ylmethylene)amino)-4,5-dihydro-1 ,2,4-triazin-3(2H)-one, 5-methyl-6-thioxo-1 ,3,5-thiadiazinan-3- ylacetic acid, 8-hydroxyquinoline sulfate, 11 -ethyl-10, 12-dioxo-2,5,8-trithia-4, 11 - diazatricyclo[7.3.0.03,7]dodeca-1 (9),3,6-triene-6-carbonitrile, 14-methyloctadec-1 -ene, [(9Z,11 E)- tetradeca-9, 11 -dienyl] acetate, [(Z)-dodec-9-enyl] acetate, abamectin, acephate, acequinocyl, acetamiprid, acethion, acetoprole, acibenzolar, acibenzolar-S-methyl, acrinathrin, Adoxophyes orana GV, Agrobacterium radiobacter, alanycarb, albendazole, aldicarb, allethrin, allosamidin, allyl alcohol, allyxycarb, alpha-ecdysone, alpha-multistriatin, Amblyseius spp., ametoctradin, amidithion, amidoflumet, amidothioate, aminocarb, amisulbrom, amiton, amiton hydrogen oxalate, amitraz, anabasine, Anagrapha falcifera NPV, Anagrus atomus, ancymidol, anilazine, anisiflupurin, anthraquinone, antu, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, athidathion, aureofungin, Autographa californica NPV, avermectin B1 a, azaconazole, azadirachtin A, azafenidin, azamethiphos, azinphos-ethyl, azinphos-methyl, azithiram, azoxystrobin, Bacillus sphaericus (Neide), Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, Bacillus thuringiensis ssp. aizawai, baculovirus, barthrin, Beauveria brongniartii, benalaxyl, benalaxyl-M, benazepril, benclothiaz, benfuracarb, benomyl, bensultap, benthiavalicarb, benzalkonium chloride, benzamorf, benzothiostrobin, benzovindiflupyr, beta-cyfluthrin, beta-cypermethrin, bethoxazin, bifenazate, bifenthrin, binapacryl, bioallethrin, bioethanomethrin, biopermethrin, bioresmethrin, bisthiosemi, bistrifluron, bitertanol, bixafen, blasticidin-S, borax, bordeaux mixture, boscalid, brodifacoum, brofenvalerate, brofluthrinate, bromadiolone, bromfenvinfos, bromophos, bromophos- ethyl, bromuconazole, bufencarb, bupirimate, buprofezin, buserelin, busulfan, but-3-ynyl N-[6-[[(Z)- [(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, butacarb, butathiofos, butocarboxim, butonate, butopyronoxyl, butoxy(polypropylene glycol), butoxycarboxi m, butylamine, cadusafos, calciferol, calcium phosphate, calcium polysulfide, cambendazole, captafol, captan, carbanolate, carbaryl, carbendazim, carbendazim hydrochloride, carbofuran, carbosulfan, carboxin, carprofen, carpropamid, cartap, cartap hydrochloride, cefalexin, cefovecin, cefquinome, ceftiour, cestex, cevadine, chinomethionat, chitosan, chlobenthiazone, chloralose, chlorantraniliprole, chlorbenside, chlordimeform, chlorethephon, chlorethoxyfos, chlorfenapyr, chlorfenazole, chlorfentazine, chlorfenvinphos, chlorfluazuron, chlormephos, chlormequat, chlorodimeform hydrochloride, chloroinconazide, chloromebuform, chloromethiuron, chloroneb, chlorothalonil, chlorphoxim, chlorprazophos, chlorpyrifos, chlorpyrifos-methyl, chlortetracycline, chlorthiophos, chlozolinate, cholecalciferol, chromafenozide, Chrysoperla carnea, cinerin, cinerin I, cinerin II, cis-jasmone, cis-resmethrin, cismethrin, clenbuterol, climbazole, cloethocarb, clofencet, clorsulon, clothianidin, clozylacon (acetamide), codlelure, copper acetate, copper hydroxide, copper naphthenate, copper octanoate, copper oleate, copper oxide, copper oxychloride, copper silicate, copper sulfate, copper(ll) carbonate, coumachlor, coumafene, coumafuryl, Coumatetralyl, coumethoxystrobin (jiaxiangjunzhi), coumithoate, coumoxystrobin, cryolite, Cryptolaemus montrouzieri, cuelure, cufraneb, cuprous(l) oxide, cyanofenphos, cyanthoate, cyazofamid, cybutryne, cyclafuramid, cyclethrin, cyclobutrifluram, Cydia pomonella GV, cyenopyrafen, cyflufenamid, cyflumetofen, cyfluthrin, cyhalothrin, cymiazole, cymoxanil, cypermethrin (alphametrin), cyphenothrin, cyproconazole, cyprodinil, cyprodinil, cyromazine, cytokinins, D- tetramethrin, Dacnusa sibirica, DAEP, dazomet, DCPM, debacarb, decarbofuran, deltamethrin, demephion-O, demephion-S, demeton-O, demeton-S, demeton-S-methyl, demeton-S- methylsulphon, diafenthiuron, dialifos, diazinon, dibutyl adipate, dibutyl phthalate, dibutyl succinate, dicapthon, dichlobentiazox, dichlofluanid, dichlone, dichlorprop, dichlorvos, dichlozoline, diclocymet, diclomezine, dicloran, dicofol, dicresyl, dicrotophos, dicyclanil, dicyclopentadiene, diethofencarb, diethyltoluamide, difenacoum, difenoconazole, difenzoquat, difethialone, diflovidazin, diflubenzuron, diflumetorim, Diglyphus isaea, dimatif, dimefluthrin, dimetan, dimethachlon, dimethipin, dimethirimol, dimethoate, dimethomorph, dimethrin, dimethyl disulfide, dimethyl phthalate, dimetilan, dimoxystrobin, dinactin, diniconazole, diniconazole-M, dinobuton, dinocap, dinocton, dinoseb, dinotefuran, diofenolan, dioxabenzofos, diphenylamine, dipyrithione, disparlure, disulfiram, disulfoton, ditalimfos, dithianon, dithicrofos, dithiocarbamate, dodec-8-en-1 -yl acetate, dodemorph, dodicin, dodine, dofenapyn, dominicalure, doramectin, drazoxolon, DSP, ecdysterone, edifenphos, emamectin benzoate, EMPC, empenthrin, Encarsia formosa, endosulfan, endothal, endothion, enestroburin (enoxastrobin), enrofloxacin, entomopathogenic bacteria, entomopathogenic fungi, entomopathogenic virus, EPBP, epoxiconazole, eprinomectin, Eretmocerus eremicus, esfenvalerate, etaconazole, ethaboxam, ethiofencarb, ethion, ethiprole, ethirimol, ethoate-methyl, ethoprophos, ethoxyquin, ethyl 4-methyloctanoate, ethyl formate, ethyl hexanediol, etofenprox, etoxazole, etridiazole, etrimfos, eugenol, eurax, EXD, exo-brevicomin, famoxadone, famphur, farnesol with nerolidol, febantel, fenamidone, fenaminstrobin, fenamiphos, fenarimol, fenazaquin, fenbendazole, fenbuconazole, fenbutatin oxide, feneptamidoquin, fenethacarb, fenfluthrin, fenfuram, fenhexamid, fenitrothion, fenobucarb, fenopyramid, fenothiocarb, fenoxacrim, fenoxanil, fenoxycarb, fenpiclonil, fenpicoxamid, fenpirithrin, fenpropathrin, fenpropidin, fenpropimorph, fenpyrazamine, fenpyroximate, fensulfothion, fenthion, fenthion-ethyl, fentin, fentin acetate, fentin chloride, fentin hydroxide, fenvalerate, ferbam, ferimzone, ferric phosphate, fipronil, flocoumafen, flonicamid, florfenicol, florylpicoxamid, fluacrypyrim, fluazinam, fluazuron, flubendazole, flubendiamide, flubeneteram, flubenzimin, flucycloxuron, flucycloxuron, flucythrinate, fludioxonil, fluenetil, flufenerim, flufenoxuron, flufenoxystrobin, flufenprox, fluindapyr, flumetralin, flumetylsulforim, flumorph, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluoxapiprolin, fluoxastrobin, fluoxytioconazole, flupyrazofos, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, fonofos, forchlorfenuron, formaldehyde, formetanate, formetanate hydrochloride, formothion, formparanate, fosetyl, fosetyl-aluminium, fosmethilan, fosthiazate, fosthietan, frontalin, fuberidazole, furalaxyl, furametpyr, furathiocarb, furethrin, furfural, gibberellic acid, glyodin, glyphosate, grandlure I, grandlure II, grandlure III, grandlure IV, guazatine triacetate, halfenprox, halofenozide, hemel, heptenophos, Heterorhabditis bacteriophora and H. megidis, hexaconazole, hexadecyl cyclopropanecarboxylate, hexaflumuron, hexalure, hexamide, hexythiazox, Hippodamia convergens, huanjunzuo (rac-(1 S,2S)-1 -(4-chlorophenyl)-2-(1 ,2,4-triazol-1 -yl)cycloheptanol), hydramethylnon, hydrated lime (calcium hydroxide), hymexazol, hyquincarb, icaridin, imanin (hypericin), imazalil, imazalil sulfate, imibenconazole, imidacloprid, iminoctadine, indoxacarb, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole, ipflufenoquin, iprobenfos (IBP), iprodione, iprovalicarb, ipsdienol, ipsenol, IPSP, isamidofos, isazofos, isocarbophos, isofetamid, isoflucypram, Isolan, isoprocarb, isoprothiolane, isopyrazam, isothioate, isotianil, isoxathion, ivermectin, japonilure, jasmolin I, jasmolin II, juvenile hormone I, juvenile hormone II, juvenile hormone III, kadethrin, kanamycin, kasugamycin, kasugamycin hydrochloride hydrate, kinetin, kinoprene, kresoxim-methyl, kurstaki, lambda-cyhalothrin, Leptomastix dactylopii, leptophos, levamisole, lineatin, lirimfos, looplure, lufenuron, Ivbenmixianan, lythidathion, m-cumenyl methylcarbamate, Macrolophus caliginosus, magnesium phosphide, malathion, maleic hydrazide, malonoben, Mamestra brassicae NPV, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mazidox, mebendazole, mecarbam, mecarphon, medlure, mefentrifluconazole, megatomoic acid, meloxicam, menazon, mepanipyrim, meperfluthrin, mephosfolan, mepiquat, mepronil, meptyldinocap, mesulfenfos, metaflumizone, metalaxyl, metalaxyl-M, metaldehyde, metam, metam-potassium, metam-sodium, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, metarylpicoxamid, metconazole, methacrifos, methamidophos, methasulfocarb, methidathion, methiocarb, methiotepa, methocrotophos, methomyl, methoprene, methoquin-butyl, methothrin, methoxyfenozide, methyl apholate, methyl eugenol, methyl iodide, methyl neodecanamide, metiram, metofluthrin, metolcarb, metominostrobin, metoxadiazone, metrafenone, metyltetraprole, mevinphos, mexacarbate, MGK 264, milbemycin, milbemycin oxime, monocrotophos, morantel tartrate, morzid, moxidectin, muscalure, myclobutanil, myclozolin, Myrothecium verrucaria composition, N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1 -methyl-pyrazole-4- carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-[(2-isopropylphenyl)methyl]-1 -methyl- pyrazole-4-carboxamide, nabam, naled, NC-170, nemadectin, Neodiprion sertifer NPV and N. lecontei NPV, niclosamide-olamine, nicotine, nicotine sulfate, nikkomycins, nitenpyram, nithiazine, nitrapyrin, nitrilacarb, nitrothal-isopropyl, norbormide, nornicotine, novaluron, noviflumuron, nuarimol, 0,0,0',0'-tetrapropyi dithiopyrophosphate, octadeca-2,13-dien-1 -yl acetate, octadeca-2,13-dien-1 - yl acetate, octhilinone, ofurace, oleic acid, omethoate, orfralure, Orius spp., orysastrobin, osthol, ostramone, oxadixyl, oxamate, oxamyl, oxantel pamoate, oxasulfuron, oxathiapiprolin, oxfendazole, oxibendazole, oxine copper, oxolinic acid, oxpoconazole, oxycarboxin, oxydemeton-methyl, oxydeprofos, oxydisulfoton, oxytetracycline, oxytetracycline dihydrate, paclobutrazol, Paecilomyces fumosoroseus, paraoxon, parathion, parathion-methyl, parbendazole, pefurazoate, penconazole, pencycuron, penethamate, penflufen, penthiopyrad, permethrin, petroleum oils, PH 60-38, phenamacril, phenthoate, phorate, phosacetim, phosalone, phosfolan, phosglycin, phosmet, phosnichlor, phosphamidon, phosphocarb, phosphonic acid, phosphorus, phoxim, phoxim-methyl, phthalide, Phytoseiulus persimilis, picarbutrazox, picoxystrobin, pimobendan, pindone, piperalin, piperonyl butoxide, piprotal, pirimetaphos, pirimicarb, pirimiphos-methyl, polycarbamate, polynactin, polyoxin B, polyoxin d, potassium ethylxanthate, potassium hydroxyquinoline sulfate, praziquantel, precocene I, precocene II, precocene III, primidophos, probenazole, prochloraz, procymidone, profenofos, profluthrin, prohexadione, prohexadione-calcium, promacyl, promecarb, propamidine, propamocarb, propaphos, propargite, propetamphos, propiconazole, propineb, propionic acid, propoxur, propyl isomer, proquinazid, prothidathion, prothioconazole, prothiofos, prothoate, protrifenbute, pymetrozine, pyraclofos, pyraclostrobin, pyrafluprole, pyrametostrobin, pyrantel pamoate, pyraoxystrobin, pyrapropoyne, pyraziflumid, pyrazophos, pyrazoxone, pyresmethrin, pyrethrin I, pyrethrin II, pyrethrins (natural products), pyrethroids (natural products), pyribencarb, pyridaben, pyridachlometyl, pyridalyl, pyridaphenthion, pyridin-4-amine, pyrifenox, pyrifluquinazon, pyrimethanil, pyrimidifen, pyrimorph, pyriofenone, pyriprole, pyriproxyfen, pyrisoxazole, pyroquilon, quassia, quinalphos, quinalphos-methyl, quinoclamine, quinofumelin, quinonamid, quinothion, quinoxyfen, quintozene, R-1492, R-metalaxyl, Reynoutria sachalinensis extract, ribavirin, rotenone, ryanodine (ryania), sabadilla, schradan, scilliroside, seboctylamine, sedaxane, selamectin, sesamex, sesamolin, siglure, silafluofen, silthiofam, simeconazole, sodium tetrathiocarbonate, sophamide, sordidin, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, spiroxamine, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., streptomycin, streptomycin sesquisulfate, sulcatol, sulcofuron, sulfiram, sulfur, sulprofos, tar oils, tau- fluvalinate, TCMTB, TDE, tebuconazole, tebufenozide, tebufenpyrad, tebufloquin, tebupirimfos, tecnazene, teflubenzuron, tefluthrin, temephos, terallethrin, terbam, terbufos, tetrachlorvinphos, tetraconazole, tetradec-11 -en-1 -yl acetate, tetradifon, tetramethrin, tetramethylfluthrin, tetranactin, thiabendazole, thiacloprid, thiadiazole copper, thiamethoxam, thiapronil, thicrofos, thicyofen, thidiazuron, thifluzamide, thiocarboxime, thiocyclam, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thiometon, thiophanate, thiophanate-methyl, thioquinox, thiosultap, thiosultap-disodium, thiram, thuringiensin, tiadinil, tiamulin, tioxymid, tolclofos-methyl, tolfenpyrad, tolprocarb, tolylfluanid, tralomethrin, transpermethrin, tretamine, triadimefon, triadimenol, triarathene, triazamate, triazophos, triazoxide, tribufos, trichlorfon, trichlormetaphos-3, trichloronat, Trichogramma spp., triclabendazole, triclopyricarb, tricyclazole, tridemorph, trifenmorph, trifloxystrobin, triflumizole, triflumuron, triforine, trimedlure, trimedlure A, trimedlure B1 , trimedlure B2, trimedlure C, trimethacarb, trinactin, trinexapac, trinexapac-ethyl, triprene, triticonazole, trunc-call, tulathromycin, Typhlodromus occidentalis, uniconazole, uredepa, validamycin, valifenalate, vamidothion, vaniliprole, veratridine, veratrine, verbutin, Verticillium lecanii, vinclozolin, XMC, xylenols, zeatin, zeta-cypermethrin, zhongshengmycin, zinc naphthenate, zinc thiazole, zineb, ziram, zolaprofos, and zoxamide.

[0035] The present invention will now be described with reference to the following examples, which are by way of illustration and do not limit the scope of the invention in any way. The following illustrative and non-limiting examples demonstrate the ability of pydiflumetofen to control dirty panicle disease (DPD).

[0036] BIOLOGICAL EXAMPLES

[0037] General Methodology

[0038] The pathogens that cause dirty panicle disease (Bipolaris oryzae, Curvularia lunata, Fusarium equiseti, Fusarium graminearum, Alternaria alternata, and Sarocladium oryzae), were isolated from infected rice tissues and stored at 4 °C. Each pathogen was applied to a PDA plate and incubated at 25 °C for 7 days. Mycelial plugs at the edge of each colony were prepared by hole puncher with a diameter of 5mm.

[0039] The fungicides pydiflumetofen (98%), propiconazole (98.3%), difenoconazole (95%), pyraclostrobin (97%), tebuconazole (97%), epoxiconazole (97.9%), prothioconazole (97%), prochloraz-copper (98.8%), and trifloxystrobin (97%) were dissolved in dimethyl sulfoxide (DMSO) to give a 1x104pg / mL stock solution of each active ingredient. Fluxapyroxad (300g / L) was diluted in autoclaved distilled water to obtain a stock solution of 1x104pg / mL. The PDA culture medium was mixed with the stock solution of each fungicide to provide a series of solutions at the following concentrations: 0, 0.001 , 0.01 , 0.1 , 0.5, 1 , 10, & 100 pg / mL.

[0040] Using the mycelial growth method, the mycelial plugs were shifted to the centre of PDA medium plates containing different fungicides concentrations. After being cultured in an incubator at 25 °C for 10 days, the diameters of every mycelial colony on PDA plates were measured and the inhibition rates were calculated. EC50 values were determined by the fitted regression line of the log- transformed percentage inhibition plotted against the log-transformed fungicide concentration. A mycelial plug with 5 mm was taken from each isolate and transferred upside down to a sterile Petri dish of 90 x 15 mm, with three replications for each concentration of fungicide. Plates were incubated at 25 ± 1 °C in darkness for 8 days. After this time, the isolates were evaluated by measuring colony diameter of mycelial growth of two perpendicular measurements of colony diameter and excluding the original plug diameter (5 mm). The mycelial growth reduction percentage for each fungicide concentration was calculated according to equation l=(D0-Dt) / (D0-0.5) (DO: colony diameter on nonamended PDA media, Dt: colony diameter on PDA media with fungicide).

[0041] The regression analysis was performed based on the logarithmic values of each concentration and the corresponding odds of mycelial growth reduction percentage for each fungicide concentration to calculate the EC50 values of pydiflumetofen, propiconazole, difenoconazole, pyraclostrobin, tebuconazole, epoxiconazole, prothioconazole, prochloraz-copper, fluxapyroxad, and trifloxystrobin against dirty panicle disease.

[0042] Example 1 : In vitro activity of pydiflumetofen, propiconazole, difenoconazole, pyraclostrobin, tebuconazole, epoxiconazole, prothioconazole, prochloraz copper, trifloxystrobin, and fluxapyroxad against dirty panicle disease caused by Bipolaris oryzae by mycelial growth method. EC50 values are shown below in Table 1 :

[0043] Table 1 :

[0044] As stated above, EC50 values were determined by the fitted regression line of the log-transformed percentage inhibition plotted against the log-transformed fungicide concentration. The lower the EC50 value, the higher the activity. The EC50 value of 0.0450 pg / mL shows that pydiflumetofen provides very high activity against Bipolaris oryzae. Example 2: In vitro activity of pydiflumetofen, propiconazole, difenoconazole, pyraclostrobin, tebuconazole, epoxiconazole, prothioconazole, prochloraz copper, trifloxystrobin, and fluxapyroxad against dirty panicle disease caused by Curvularia lunata by mycelial growth method. EC50 values are shown below in Table 2:

[0045] Table 2:

[0046] As stated above, EC50 values were determined by the fitted regression line of the log-transformed percentage inhibition plotted against the log-transformed fungicide concentration. The lower the EC50 value, the higher the activity. The EC50 value of 0.0148 pg / mL shows that pydiflumetofen provides very high activity against Curvularia lunata.

[0047] Example 3: In vitro activity of pydiflumetofen, propiconazole, difenoconazole, pyraclostrobin, tebuconazole, epoxiconazole, prothioconazole, prochloraz copper, trifloxystrobin, and fluxapyroxad against dirty panicle disease caused by Fusarium equiseti by mycelial growth method. EC50 values are shown below in Table 3:

[0048] Table 3:

[0049] As stated above, EC50 values were determined by the fitted regression line of the log-transformed percentage inhibition plotted against the log-transformed fungicide concentration. The lower the EC50 value, the higher the activity. The EC50 value of 0.6537 pg / mL shows that pydiflumetofen provides very high activity against Fusarium equiseti.

[0050] Example 4: In vitro activity of pydiflumetofen, propiconazole, difenoconazole, pyraclostrobin, tebuconazole, epoxiconazole, prothioconazole, prochloraz copper, trifloxystrobin, and fluxapyroxad against dirty panicle disease caused by Fusarium graminearum by mycelial growth method. EC50 values are shown below in Table 4:

[0051] Table 4:

[0052] As stated above, EC50 values were determined by the fitted regression line of the log-transformed percentage inhibition plotted against the log-transformed fungicide concentration. The lower the EC50 value, the higher the activity. The EC50 value of 0.0031 pg / mL shows that pydiflumetofen provides very high activity against Fusarium graminearum.

[0053] Example 5: In vitro activity of pydiflumetofen, propiconazole, difenoconazole, pyraclostrobin, tebuconazole, epoxiconazole, prothioconazole, prochloraz copper, trifloxystrobin, and fluxapyroxad against dirty panicle disease caused by Alternaria alternata by mycelial growth method. EC50 values are shown below in Table 5:

[0054] Table 5:

[0055] As stated above, EC50 values were determined by the fitted regression line of the log-transformed percentage inhibition plotted against the log-transformed fungicide concentration. The lower the EC50 value, the higher the activity. The EC50 value of 0.0204 pg / mL shows that pydiflumetofen provides very high activity against Altemaria altemata.

[0056] Example 6: In vitro activity of pydiflumetofen, propiconazole, difenoconazole, pyraclostrobin, tebuconazole, epoxiconazole, prothioconazole, prochloraz copper, trifloxystrobin, and fluxapyroxad against dirty panicle disease caused by caused by Sarocladium oryzae by mycelial growth method. EC50 values are shown below in Table 6:

[0057] Table 6:

[0058] As stated above, EC50 values were determined by the fitted regression line of the log-transformed percentage inhibition plotted against the log-transformed fungicide concentration. The lower the EC50 value, the higher the activity. The EC50 value of 0.0435 pg / mL shows that pydiflumetofen provides very high activity against Sarocladium oryzae.

[0059] The above results show that pydiflumetofen consistently provides good control against all six pathogens known to cause rice dirty panicle disease (DPD), compared to fungicides presently used to control rice dirty panicle disease (DPD).

[0060] Example 7: Efficacy of pydiflumetofen against DPD in rice in the field at 46 days after second application

[0061] Application Method: Foliar Spray; Water Volume: 450 L / ha; Application Timing: 1 Application: BBCH 43, 2 Applications: BBCH 43 + BBCH 58

[0062] Table 7:

[0063] *Market standard

[0064] A scale / index of 0 to 9 was used to define the level of disease severity, wherein 0 represents a healthy plant and 9 represents high levels / severe symptoms of disease. Each plant was graded on this 0 to 9 scale and the Disease Index calculated using the following formula:

[0065] Disease Index (DI) = [sum (class frequency x score of rating class)] / [(total number of plants) x (maximal disease index)] x 100.

[0066] The results in Table 7 show that one application of pydiflumetofen at a rate of 75gai / ha provides equivalent results in the field to the market standard for the control of DPD in rice at 46 days after second application. However, two applications of pydiflumetofen at a rate of 75gai / ha provides superior results to the market standard for the control of DPD in rice at 46 days after second application. Example 8: Efficacy of pydiflumetofen against DPD in rice in the field at 58 days after application

[0067] Application Method: Foliar Spray; Water Volume: Drone application 75 L / ha; Application Timing: BBCH 43

[0068] Table 8:

[0069] *Market standard

[0070] The results in Table 8 show that one application of pydiflumetofen at a rate of 75gai / ha provides superior results to the market standard for the control of DPD in rice at 58 days after first application.

[0071] Example 9: Efficacy of pydiflumetofen against DPD in rice in the field at 40 days after application

[0072] Application Method: Foliar Spray; Water Volume: 450 L / ha; Application Timing: BBCH 58 Table 9:

[0073] *Market standard

[0074] The results in Table 9 show that one application of pydiflumetofen at a rate of 75gai / ha provides superior results to the market standard for the control of DPD in rice at 40 days after application

Claims

CLAIMS1 . A method of controlling dirty panicle disease on rice plants, said method comprising applying an effective amount of pydiflumetofen, to the plant, plant part, propagation material of the plant, or to the locus thereof.

2. The method according to claim 1 , comprising applying an effective amount of a composition comprising pydiflumetofen, to the plant, plant part, propagation material of the plant, or to the locus thereof.

3. The method according to claim 1 or claim 2, wherein pydiflumetofen is applied during the reproductive growth stage of the rice plant.

4. The method according to any one of claims 1 to 3, wherein pydiflumetofen is applied during the early- to mid-boot stage of rice plant growth.

5. The method according to any one of claims 1 to 4, wherein pydiflumetofen is applied to the plant, plant part, or locus thereof in an amount from 20 g per hectare to 600 g per hectare.

6. The method according to any one of claims 1 to 5, wherein pydiflumetofen is applied to the plant, plant part, or locus thereof in an amount from 50 g per hectare to 100 g per hectare.

7. A method of controlling the growth of Bipolaris oryzae, Curvularia lunata, Fusarium equiseti, Fusarium graminearum, Alternaria alternata and / or Sarocladium oryzae on rice plants, plant parts or propagation material, said method comprising applying an effective amount of pydiflumetofen, to the plant propagation material, a plant part, plant, or locus thereof.

8. The method according to any one of claims 1 to 7, wherein the composition is applied using foliar spraying, as a seed treatment and / or wherein the composition is applied through soil drenching.

9. A fungicidal composition for treating dirty panicle disease in rice, comprising 0.1 -5% by weight of pydiflumetofen, and of from 95-99.9% by weight of agriculturally acceptable carriers, adjuvants, and solvents.

10. A use of pydiflumetofen for the manufacture of a fungicidal composition for controlling dirty panicle disease in rice.

11. A rice crop or rice grain treated by the method of claim 1 , exhibiting reduced incidence of dirty panicle disease.

12. Use of pydiflumetofen, or an agrochemically acceptable salt, isomer, stereoisomer, diastereoisomer, enantiomer or tautomer thereof, to control dirty panicle disease on rice plants.

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