New uses of pydiflumetofen

Abstract

The present invention relates to the use of N-methoxy(phenylethyl)-pyrazolecarboxamides for controlling phytopathogenic diseases, in particular phytopathogenic fungi, in useful plants and to a method for controlling such diseases and / or fungi in 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 controlling Ustilaginoidea spp., in particular Ustilaginoidea virens, in rice plants.

Description

[Technical Field]

[0001] The present invention relates to the use of N-methoxy(phenylethyl)-pyrazolecarboxamides for controlling phytopathogenic diseases, in particular phytopathogenic fungi, in useful plants and to a method for controlling such diseases and / or fungi in 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 controlling Ustilaginoidea spp., in particular Ustilaginoidea virens, in rice plants. [Background technology]

[0002] It is known from WO 2008 / 148570, WO 2010 / 063700, WO 2010 / 084078 and WO 2008 / 151828 that certain pyrazolyl-carboxamide derivatives have biological activity against plant pathogenic fungi. On the other hand, various fungicidal compounds of different chemical classes are widely known as plant fungicides for use in various crops of cultivated plants.

[0003] Ustilaginoidea virens is a plant pathogen that causes rice "smut," a disease known to reduce both grain yield and grain quality. Rice smut primarily affects quality because the fungus produces brown "teliospores" that contaminate rice grains at harvest; that is, the pathogen converts individual kernels in the young rice panicle into teliospores, which become covered with powdery chlamydospores during maturation. These are unsightly, and if there are too many of these spores in a shipment, the rice must be removed before it can be used. It can also cause problems for exported rice.

[0004] Ustilaginoidea virens has a unique life cycle in which white hyphae are produced by the fungus after initial infection of the floral organs of rice crops. As the infection matures over time, darker brownish-green chlamydospores are produced on the rice spikelets. Additionally, sclerotia may be present in late autumn. During its life cycle, U. virens passes through sexual (ascospore) and asexual (chlamydospore) stages. Chlamydospores are the primary survival structure, and they can survive in the soil for up to four months. The formation of additional sclerotia allows U. virens to survive even longer, up to nearly a year. These sclerotia can reside either on or below the soil surface and mature to form ascocarps (fruiting bodies). Ascospores from these fruiting bodies act as the primary source of infection, spreading the disease throughout the rice field. The disease is most severe when environmental conditions such as high humidity (greater than 80%) and temperatures in the range of 25°C to 30°C prevail. Late sowing of rice plants and high soil fertility, as well as large amounts of manure in the soil, lead to an increase in the disease.

[0005] 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 widely used (especially in China) for the control of rice diseases such as rice sheath blight, rice blast, and rice mildew.

[0006] 3-(Difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide (known by its generic name "pydiflumetofen"), described in WO 2010 / 063700, is a broad-spectrum foliar fungicide and the first example of a new group of N-methoxy-(phenylethyl)-pyrazole-carboxamides belonging to the succinate dehydrogenase inhibitor (SDHI) class. Summary of the Invention [Means for solving the problem]

[0007] The present invention is based on the surprising discovery that pydiflumetofen also exhibits high levels of activity against Ustilaginoidea virens in rice plants.

[0008] Thus, in a first aspect, the present invention relates to a method for controlling Ustilaginoidea virens in rice plants, the method comprising applying an effective amount of pydiflumetofen to the plant, plant part, or its habitat.

[0009] In another aspect, a method for controlling Ustilaginoidea virens in rice plants is provided, comprising applying to the plant, plant part, or its habitat a composition comprising an effective amount of pydiflumetofen.

[0010] In a further aspect, there is provided use of pydiflumetofen or an agrochemically acceptable salt, isomer, stereoisomer, diastereoisomer, enantiomer or tautomer thereof for controlling Ustilaginoidea virens.

[0011] Pydiflumetofen and its preparation are described in WO 2010 / 063700, WO 2013 / 127764, and WO 2014 / 206855. Those skilled in the art will recognize that 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide exists in two enantiomeric forms: 3-(difluoromethyl)-N-methoxy-1-methyl-N-[(1R)-1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide and 3-(difluoromethyl)-N-methoxy-1-methyl-N-[(1S)-1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide. Both enantiomers can be used individually or as racemates to control or suppress plant pathogenic bacteria. The compound 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide may be referred to herein by its full name, its ISO name, or as "the compound." DETAILED DESCRIPTION OF THE INVENTION

[0012] As used herein, the term "habitat" means the field in which the plant is growing, or the field in which the seeds of the cultivated plant are sown, or the field in which the seeds will be sown in the soil. It includes the soil, the seeds and seedlings, and the established vegetation.

[0013] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, roots, stems, stalks and foliage.

[0014] The term "plant propagation material" as used herein is understood to mean the propagation parts of useful plants, such as seeds that can be used for their propagation, and vegetative material, such as cuttings or tubers (e.g., potatoes). Examples include seeds (in the strict sense), roots, fruits, tubers, bulbs, corms, rhizomes, and plant parts. Also included are sprouted plants and young shoots that will be transplanted after germination or emergence from the soil. Such young plants can be protected before transplanting by complete or partial treatment by immersion in a compound. Preferably, "plant propagation material" is understood to mean seeds and / or roots, more preferably seeds.

[0015] The term "reproductive stage" refers to the final stage of plant growth following germination and vegetative growth. During the reproductive stage, the plant's energy is directed toward the production of flowers, fruits, and seeds. Several growth stages help identify critical periods in the rice crop's life cycle. They are generally divided into stages primarily associated with either vegetative or reproductive development. The vegetative stage occurs first and is associated with a period of 6 to 8 weeks after planting. This is followed by the reproductive stage, which is generally associated with the formation, development, and maturation of panicles and kernels. Panicle differentiation is the first stage of the reproductive stage of growth.

[0016] Reproductive stages typically begin with the beginning of stem elongation (BBCH30). In rice, reproductive stages include panicle differentiation (BBCH30), panicle initiation (BBCH32), internode elongation (BBCH34), spikelet differentiation (BBCH35), meiosis (BBCH39), booting (BBCH41-49), and heading (BBCH51). In wheat, reproductive stages include first node formation (BBCH31), flag leaf formation (BBCH37), booting (BBCH41-49), and heading (BBCH50-59).

[0017] The developing young panicle is microscopic in size within the stem, and panicle differentiation is usually associated with the onset of stem internode formation. As the internode elongation stage begins, chlorophyll accumulation occurs in the internodes that are separated in the process of forming the first stem internode. This chlorophyll accumulation confers a green color around the growing internode, creating a green ring or band. Therefore, the internode elongation stage is sometimes referred to as the green ring stage. This stage is also called the first green ring because additional internodes formed above the first internode may also have the green ring effect as they begin to form. During rice stem formation, a total of five internodes can be generated. As internode and panicle formation continues, the panicle differentiation stage occurs. This is the first stage of the reproductive phase, when the newly formed young panicle becomes visible. At this stage, the young panicle inside the stem has grown to about 1 / 8 inch. In metric terms, it is about 2 millimeters long, and this stage is sometimes referred to as the 2-mm young panicle stage. The young panicle continues to grow and develop inside the stem. The growth stage is then called booting and is identified by the length of the young panicle. When the young panicle is up to 2 inches long, the growth stage is the early booting stage. The mid-booting and late booting stages occur when the young panicle is 2-5 inches and over 5 inches long, respectively. Up to this point, identifying the reproductive growth stage requires dissecting the stalk (splitting it in half). During the late booting stage, the young panicle is fully developed, and subsequent growth stages occur after the young panicle emerges and becomes visible outside the stalk. The heading stage is indicated when part of the young panicle is observed growing from the end of the rice stalk. From this point on, the growth stage is based on the appearance of the young panicle outside the rice stalk. The heading stage is identified by percentage, with the 50 percent heading stage occurring when 50 percent of the rice stalk has emerged or has emerged (the young panicle has completely emerged from the stalk).

[0018] In one embodiment, the crop plants are at a BBCH growth stage of 30 to 51 at the time of treatment. In a further embodiment, the crop plants are at a BBCH growth stage of 41 to 49 at the time of treatment. In a further embodiment, the crop plants are at a BBCH growth stage of 45 to 47. In one embodiment, the crop plants are treated after the onset of the reproductive growth stage. In a further embodiment, the crop plants are treated before the heading growth stage, which corresponds to BBCH growth stage 51.

[0019] For the control of Ustilaginoidea virens, pydiflumetofen is applied or administered in an "effective amount," meaning that at the appropriate application time, is sufficient to achieve the desired level of control of Ustilaginoidea virens.

[0020] Pydiflumetofen for controlling Ustilaginoidea virens can be used in its unmodified form or, preferably, with carriers and adjuvants conventionally used in the formulation art, as described, for example, in WO 2010 / 063700. Typically, when used for fungal control, pydiflumetofen is applied to useful plants by foliar spray. However, for controlling Ustilaginoidea virens, the preferred application method is directly to the plant, the plant's habitat (e.g., soil), or plant propagation material (e.g., seed application).

[0021] In a further embodiment, pydiflumetofen is applied to the plant, plant part, or its habitat in the form of a fungicidal formulation, which may contain one or more other desirable ingredients, including, but not limited to, a liquid diluent, a binder to serve as a substrate for the compounds described herein, a filler to protect the seeds, and a plasticizer to improve the flexibility, adhesion, and / or spreadability of the coating.

[0022] Compositions comprising fungicidal formulations, for example pydiflumetofen, and, if necessary, solid or liquid adjuvants or monomers for encapsulating the compounds, can be prepared in known manner, typically by mixing and / or grinding the compounds with extenders, such as solvents, solid carriers, and optionally surface-active compounds (surfactants).

[0023] Typical application rates per hectare are generally 1 g to 2000 g of pydiflumetofen per hectare, particularly 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 to treat seeds or as a drench, convenient application rates are 1 mg to 50 g of active substance per kg of seed, preferably 10 mg to 30 g of active substance per kg of seed, and more preferably 10 mg to 1 g of active substance per kg of seed.

[0024] In a further embodiment, pydiflumetofen is used in a foliar or seed treatment composition.

[0025] The compositions of the present invention may be in any conventional form, such as, for example, two-part systems, dry seed treatment powders (DS), seed treatment emulsions (ES), seed treatment flowable concentrates (FS), seed treatment solutions (LS), seed treatment water dispersible powders (WS), seed treatment capsule suspensions (CF), seed treatment gels (GF), emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (WG), etc. (EG), emulsion, water-in-oil (EO), emulsion, oil-in-water (EW), microemulsion (ME), oil dispersion (OD), oil-miscible flowable (OF), oil-miscible liquid (OL), soluble concentrate (SL), ultra-low volume suspension (SU), ultra-low volume liquid (UL), technical concentrate (TK), dispersible concentrate (DC), wettable powder (WP), or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0026] Such compositions can be prepared in a conventional manner, for example, by mixing the active ingredient with suitable formulation inerts (diluents, solvents, fillers, and optionally other formulation ingredients such as surfactants, biocides, antifreeze agents, spreading agents, thickeners, and compounds providing auxiliary effects). Conventional sustained-release formulations can also be employed when long-lasting effectiveness is intended. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, can contain surfactants, such as wetting agents and dispersants, as well as other compounds providing auxiliary effects, such as condensation products of formaldehyde with naphthalenesulfonates, alkylarylsulfonates, ligninsulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0027] Typically, the formulation contains 0.01 to 90% by weight of the active agent, 0 to 20% by weight of an agriculturally acceptable surfactant, and 10 to 99.99% by weight of solid or liquid inert compounding agents and adjuvants, where the active agent is at least pydiflumetofen, optionally containing components (B) and (C), and other active agents, particularly fungicides or preservatives. Concentrated forms of the composition generally contain about 2 to 80% by weight, preferably about 5 to 70% by weight, of the active agent. The application form of the formulation may contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight, of the active agent. While commercial products are preferably formulated as concentrates, end users typically utilize diluted formulations.

[0028] Pydiflumetofen may be the only active ingredient in the composition or, where appropriate, may be mixed with one or more additional active ingredients, such as pesticides, fungicides, synergists, herbicides or plant growth regulators, which may in some cases result in unexpected synergistic activity.

[0029] Examples of suitable additional active ingredients include petroleum, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenylbenzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenylphenylsulfone, acetoprole, aldoxicarb, amidithione, amidothioate, amiton, amiton hydrogen oxalate, amitraz, alamite, arsenic trioxide, azobenzene, azotoate, benomyl, benoxafos, benzyl benzoate, bicarbonate, Xaphen, Brofenvalerate, Bromocyclen, Bromophos, Bromopropylate, Buprofezin, Butocarboxim, Butoxycarboxim, Butylpyridaben, Calcium polysulfide, Camphechlor, Carbanolate, Carbophenothion, Cymiazole, Chinomethionate, Chlorbeside, Chlordimeform, Chlordimeform Hydrochloride, Chlorphenetole, Chlorfenson, Chlorphenesulfide, Chlorbenzilate, Chlormebuform, Chlormethionon, Chlorpropyl ate, chlorthiophos, cinerin I, cinerin II, cinerin, closantel, coumaphos, crotamiton, crotoxyphos, khuraneb, cyanthoate, DCPM, DDT, demefion, demefion-O, demefion-S, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methyl sulfone, dichlofluanid, dichlorvos, dicrifos, dienochlor, dimefox, zinex, zinex-diclexin, zinocap -4, dinocap-6, dinoctone, dinopentone, dinosulfone, dinotervone, dioxathion, diphenylsulfone, disulfiram, DNOC, dofenapine, doramectin, endothion, eprinomectin, ethoate-methyl, etrimphos, fenazaflor, fenbutatin oxide, fenothiocarb, fenpyrad, fenpyroximate, fenpyrazamine, fenson, fentrifanil, flubenzimine, flucycloxuron, fluenethyl, fluorbenside, FMC 1137, formetanate, formetanate hydrochloride, formparanate, γ-HCH, gliodin, halfenprox, hexadecylcyclopropanecarboxylate, isocarbophos, jasmolin I, jasmolin II,Iodofenphos, lindane, malonobene, mecarbam, mefosfolan, mesulfen, methacrifos, methyl bromide, metolcarb, mexacarbate, milbemycin oxime, mipafox, monocrotophos, morphothion, moxidectin, naled, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, nifururidide, nikkomycin, nitrilacarb, nitrilacarb 1:1 zinc chloride complex, omethoate, oxydeprophos, oxydisulfoton, pp'-DDT, pa Lathion, permethrin, fencaptone, phosalone, phospholane, phosphamidon, polychloroterpenes, polynactin, proclonol, promacyl, propoxar, prothidathion, prothoate, pyrethrin I, pyrethrin II, pyrethrins, pyridaphenthion, pirimitate, quinalphos, quintiox, R-1492, phosglycine, rotenone, shradan, cebufos, selamectin, sofamid, SSI-121, sulfiram, sulfuramide, sulfotep, sulfur, diflobidazin, tau-fluvalinate, TEPP, terbam, tet Radifon, tetrasulf, thiafenox, thiocarboxim, thiofanox, thiometon, thioquinox, thuringiensin, triamiphos, triatene, triazophos, triazuron, triphenofos, trinactin, vamidothion, vaniliprole, bethoxazin, copper dioctanoate, copper sulfate, sibutrin, dichloron, dichlorophen, endothall, fentin, hydrated lime, nerbam, quinoclamine, quinonamide, simazine, triphenyltin acetate, triphenyltin hydroxide, crufomate, piperazine, thiophanate, chloralose, fu ethylenediamine, pyridin-4-amine, strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxalin-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, dipyrithione, dodisin, fenaminosulf, formaldehyde, hydralgafen, kasugamycin, kasugamycin hydrochloride hydrate, nickel bis(dimethyldithiocarbamate), nitrapyrin, octhilinone, oxolinic acid, oxytetracycline, potassium hydroxyquinoline sulfate, probenazole,Streptomycin, streptomycin sesquisulfate, tecloftalam, thiomersal, Adoxophyes orana GV, Agrobacterium radiobacter, Amblyseius spp., Anagrapha falcifera NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus Neide, Beauveria bronniartii brongniartii, Chrysoperla carnea, Cryptolaemus montrouzieri, Cydia pomonella GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Heterorhabditis bacteriophora and H. megidis, Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus caliginosus), Mamestra brassicae NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae,Neodiprion sertifer NPV and N. lecontei NPV, Orius spp., Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisi, scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis, Verticillium lecanii lecanii), apholate, visadil, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl apholate, molzide, penfluron, tepa, thiohempa, thiotepa, trethamine, uredepa, (E)-dec-5-en-1-ol with (E)-dec-5-en-1-yl acetate, (E)-tridec-4-en-1-yl acetate, (E)-6-methylhept-2-en-4-ol, (E,Z)-tetradec-4,10-dien-1-yl acetate , (Z)-dodec-7-en-1-yl acetate, (Z)-hexadec-11-enal, (Z)-hexadec-11-en-1-yl acetate, (Z)-hexadec-13-en-11-yn-1-yl acetate, (Z)-icosa-13-en-10-one, (Z)-tetradec-7-en-1-al, (Z)-tetradec-9-en-1-ol, (Z)-tetradec-9-en-1-yl acetate, (7E,9Z)-dodeca-7,9-dien-1-yl acetate,(9Z,11E)-Tetradeca-9,11-dien-1-yl acetate, (9Z,12E)-Tetradeca-9,12-dien-1-yl acetate, 14-methyloctadec-1-ene, 4-methylnonan-5-one with 4-methylnonan-5-ol, α-multistriatin, brevicomin, codrelure, codlemone, curure, disparure, dodec-8-en-1-yl acetate, dodec-9-en-1-yl acetate, dodec-8,10-dien-1-yl acetate, dominicalure, ethyl 4-methyloctanoate, eugenol ol, frontalin, grandol, grandol I, grandol II, grandol III, grandol IV, hexalure, ipsdienol, ipsenol, japonilure, lineatin, litalure, lupulure, medulure, megatomoic acid, methyl eugenol, muscalure, octadeca-2,13-dien-1-yl acetate, octadeca-3,13-dien-1-yl acetate, orfuralure, orictalure, ostramon, siglua, sordidin, sulcatol, tetradec-11-en-1-yl acetate, trimedulure, trimedol A A, Trimedlure B1, Trimedlure B2, Trimedlure C, Tranquol, 2-(octylthio)ethanol, Butopyronoxyl, Butoxy (polypropylene glycol), Dibutyl adipate, Dibutyl phthalate, Dibutyl succinate, Diethyl toluamide, Dimethylcarbate, Dimethyl phthalate, Ethyl hexanediol, Hexamide, Methoxybutyl, Methyl neodecaneamide, Oxamate, Picaridin, 1-Dichloro-1-nitroethane, 1,1-Dichloro-2,2-bis(4-ethylphenyl)ethane, 1,2-Dichloropropane 1,3-dichloropropene, 1-bromo-2-chloroethane, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate, 2-(1,3-dithiolan-2-yl)phenyl dimethyl carbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate, 2-(4-chloro-3,5-xylyloxy)ethanol, 2-chlorovinyl diethyl phosphate,2-Imidazolidone, 2-Isovalerylindan-1,3-dione, 2-Methyl(prop-2-ynyl)aminophenylmethylcarbamate, 2-Thiocyanatoethyl laurate, 3-Bromo-1-chloroprop-1-ene, 3-Methyl-1-phenylpyrazol-5-yldimethylcarbamate, 4-Methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate, 5,5-Dimethyl-3-oxocyclohex-1-enyldimethylcarbamate, acetione, acrylonitrile, aldrin, allosamidin, alixycarb, α-ecdysone, aluminum phosphide, aminocarb, anabasine, atidathion, azamethiphos, Bacillus thuringiensis delta-endotoxin, barium hexafluorosilicate, barium polysulfide, bartholin, Bayer 22 / 190, Bayer 22408, β-cyfluthrin, β-cypermethrin, bioethanomethrin, biopermethrin, bis(2-chloroethyl)ether, borax, bromfenvinphos, bromo-DDT, bufencarb, butacarb, butathiophos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, sevadin, chlorbicyclen, chlordane, chlordecone, chloroform, chloropicrin, chlorphoxim, chlorprazophos, cis-resmethrin, cismethrin, clocitrin, copper acetoarsenite, copper arsenate, copper oleate, cumitoate, cryolite, CS 708, cyanofenphos, cyanophos, cyclethrin, cythioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidaphos, dikapton, diclofenthion, dicresyl, dicyclanil, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dilol, dimefluthrin, dimethane, dimethrin, dimethylvinphos, dimethyllan, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzophos, dicyclophos, DSP, ecdysterone, EI 1642, EMPC, EPBP, etaphos, ethiofencarb, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, EXD, fenchlorphos, fenetacarb, fenitrothion, fenoxacrim, fenpyrithrin, fensulfothion,Fenthion-ethyl, Flucofuron, Fosmetilan, Fospirate, Fostietan, Furathiocarb, Frethrin, Guazatine, Guazatine acetate, Sodium tetrathiocarbonate, Halfenprox, HCH, HEOD, Heptachlor, Heterofos, HHDN, Hydrogen cyanide, Hikincarb, IPSP, Isazophos, Isobenzan, Isodrin, Isofenphos, Isolane, Isoprothiolane, Isoxathion, Juvenile hormone I, Juvenile hormone II, Juvenile hormone III, Kerevan, Kinoprene, Lead arsenate, Leptophos, Lilimphos, Ritidathion, m-Cumenylmethylcarbamate, Magnesium phosphide, Magidox, Mecarfone, Menasone, Mercurous chloride, Mesulfenphos, Metam, Metam-potassium, Metam-sodium, Meta fluoride Tansulfonyl, methocrotophos, methoprene, methothrin, methoxychlor, methyl isothiocyanate, methyl chloroform, methylene chloride, methoxadiazone, Mirex, naphthalophos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, nornicotine, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate, O,O,O',O'-tetrapropyl dithiopyrophosphate, oleic acid, para-dichlorobenzene, parathion-methyl, pentachlorophenol, pentachlorophenyl laurate, PH 60-38, fenkapton, phosniclor, phosphine, phoxim-methyl, pyrimetaphos, polychlorodicyclopentadiene isomers, potassium arsenite, potassium thiocyanate, precocene I, precocene II, precocene III, primidophos, profluthrin, promecarb, prothiofos, pyrazophos, pyresmethrin, quassia, quinalphos-methyl, quinothion, rafoxanide, resmethrin, rotenone, kadethrin, ryania, ryanodine, sabadila, shradan, cebufos, SI-0009, tiapronil, sodium arsenite, sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenoxide, sodium selenate, sodium thiocyanate, sulcofuron,Sulcofuron sodium, sulfuryl fluoride, sulproos, tall oil, thazimcarb, TDE, tebupirimfos, temephos, telalethrin, tetrachloroethane, cyclofos, thiocyclam, thiocyclam hydrogen oxalate, thionazine, thiosultap, thiosultap-sodium, tralomethrin, transpermethrin, triazamate, trichlormetaphos-3, trichloronate, trimethacarb, tolprocarb, triclopiricarb, triplen, veratridine, veratrine, XMC, zetamethrin, zinc phosphide, zolaprofos, meperfluthrin, tetramethylfluthrin, bis(thiazolinone) Tributyltin oxide, bromoacetamide, ferric phosphate, niclosamido-olamine, tributyltin oxide, pyrimorph, triphenmorph, 1,2-dibromo-3-chloropropane, 1,3-dichloropropene, 3,4-dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid, 6-isopentenylaminopurine, anicifluprine, benclotiaz, cytokinin, DCIP, furfural, isamidophos, kinetin, mulberry dark spot fungus (Myrothecium verrucaria) compound, tetrachlorothiophene, xylenol, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, Reynoutria sachalinensis) extract, α-chlorohydrin, anth, barium carbonate, bisthiosemi, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuryl, coumatetralyl, crimidine, difenacoum, difethialone, diphacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropazine, flupropazine hydrochloride, norbormide, fosacetim, phosphorus, pindone, pyrinuron, sciliroside, sodium fluoroacetate, thallium sulfate, warfarin, 2-(2-butoxyethoxy)ethyl piperonylate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, nerolidol with farnesol, berubutin, MGK 264, piperonyl butoxidePiprotal, propyl isomers, S421, sesamex, sesamolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, thiram, zinc naphthenate, ziram, imanin, ribavirin, chlorinconazide, mercuric oxide, thiophanate-methyl, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furametpyr, hexaconazole, imazalil, imibe Nconazole, ipconazole, metconazole, myclobutanil, paclobutrazol, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, ancymidol, fenarimol, nuarimol, bupirimate, dimethirimol, ethirimol, dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, cyprodinil , mepanipyrim, pyrimethanil, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofrace, oxadixyl, carbendazim, debacarb, fuberidazole, thiabendazole, chlozolinate, diclozolin, mycrozolin, procymidone, vinclozolin, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, dodine, iminoctadine, azoxystrobin, dimoxystrobin, enesterobrine, fenamins strobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, oryzastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, ferbam, mancozeb, maneb, metiram, propineb, zineb, captafol, captan, fluoroimide, folpet, tolylfluanid, Bordeaux mixture, copper oxide, mancopper, oxine-copper, nitrotar-isopropyl, edifenphos, iprobenfos, phosdifen, tolclofos-methyl,Anilazine, Benthiavalicarb, blasticidin-S, chloroneb, chlorothalonil, cyflufenamid, cymoxanil, cyclobutrifluram, diclocymet, diclomedine, dicloran, diethofencarb, dimethomorph, flumorph, dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, ferimzone, fluazinam, flumethylsulfolim, fluopicolide, fluoxythioconazole, flusulfamide, fluxapyroxad, fenhexamid, fosetyl-aluminum, hymexazole, ipro Valicarb, cyazofamid, metasulfocarb, metrafenone, pencycuron, phthalide, polyoxin, propamocarb, pyribencarb, proquinazide, pyroquilon, pyriophenone, quinoxyfen, quintozene, tiadinil, triazoxide, tricyclazole, triforine, validamycin, valifenalate, zoxamide, mandipropamide, flubenetram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-tri ... (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyridine-3-carbonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide ... 4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, fluindapyr, methoxystrobin (jiaxiangjunzhi), rubenmixianan, dichlorbenziazox, mandestrobin, 3-(4,4-Difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, oxathiapiproline, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, pyraziflumide, impirfluxam, tolprocarb, mefentrifluconazole, ipfentrifluco thiazol-1-yl]acetyl]-4-piperidyl]thiazole, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazole- 4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine, pyridaclomethyl, 3 -(Difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one, aminopyrifen, ametoctrazine, amisulbrom, penflufen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, florylpicoxamide, fenpicoxamide, methallylpicoxamide, tebufloquine, ipflufenoquine, quinofumelin, isofetamide, ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate (which can be prepared from the method described in WO 2020 / 056090) , ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate (which can be prepared from the method described in WO 2020 / 056090), methyl N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (which can be prepared from the method described in WO 2020 / 097012), methyl N-[[4-[1-(2,6-difluoro 2-(2,4-dimethylphenyl)-4-isopropyl-2-pyrazol-4-yl)-2-methyl-phenyl]methyl]carbamate (which can be prepared from the method described in WO 2020 / 097012), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (which can be prepared from the method described in WO 2020 / 109391), 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)- N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (which can be prepared from the method described in WO 2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (which can be prepared from the method described in WO 2020 / 109391), N-[2-[2,4-Dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, benzothiostrobin, fenamacril, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1), Fluopyram, flufenoxadiazam, fluthianil, fluopimomide, pyrapropoin, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxidase [4-(trifluoromethyl)triazol-2-yl]phenoxy]benzonitrile, methyltetraprole, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol, fluoxapiproline, enoxastrobin, methyl (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate, methyl (Z)-3-methyl methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (these compounds can be prepared from the method described in WO 2020 / 079111), methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (these compounds can be prepared from the method described in WO 2020 / 193387), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile Zonitrile, trinexapac, cumoxystrobin, zhongshengmycin, copper thiodiazole, zinc thiazole, amethotractin, iprodione, seboxylamine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds are described in International Publication No. 20 15 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared by the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared from the method described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2 -trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds can be prepared from the method described in WO 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]- N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared from the method described in WO 2017 / 153380); 1-(6,7- Dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline isoquinoline, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds can be prepared from the method described in WO 2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline , 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds can be prepared from the method described in WO 2016 / 156085);N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl) -1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, [phenyl]phenyl]methyl]-1,2,4-triazol-3-amine (these compounds can be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689); 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from the method described in WO 2017 / 029179);2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (this compound can be prepared from the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (this compound can be prepared from the method described in WO 2014 / 006945); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide (which can be prepared from the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound can be prepared from the method described in WO 2018 / 153707); N'- (2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared from the method described in WO 2014 / 095675);(5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds can be prepared from the method described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared from the method described in WO 2018 / 065414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (this compound can be prepared from the method described in WO 2018 / 065414). 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared by the method described in WO 2018 / 202428).

[0030] The present invention will now be described with reference to the following examples, which are intended for illustrative purposes and are not intended to limit the scope of the invention in any way. The following examples demonstrate the ability of pydiflumetofen to control Ustilaginoidea virens. [Example]

[0031] Biological Examples Example 1 - In vitro activity of pydiflumetofen against rice mildew (caused by Ustilaginoidea virens) by mycelial growth method Ustilaginoidea virens, the pathogen that causes rice mildew, was isolated from infected rice tissue and stored at 4°C. The pathogen was applied to PSA plates and incubated at 28°C for 7 days. Mycelial plugs from the edge of the colony were prepared using a 5 mm diameter punch. Pydiflumetofen was dissolved in dimethyl sulfoxide (DMSO) to prepare a stock solution of 4 × 10 4 The PSA culture medium was mixed with a stock solution of pydiflumetofen to obtain a series of different concentrations: 0, 0.0005, 0.0010, 0.0025, 0.0040, 0.0055, and 0.007 μg / mL. Using the mycelial growth method, mycelial plugs were transferred to the center of PSA medium plates containing different pydiflumetofen concentrations. After 14 days of culture in an incubator at 28°C, the diameters of all mycelial colonies on the PSA plates were measured, and the inhibition rate was calculated. EC 50 Values were determined by fitting a regression line of log-transformed percentage inhibition plotted against log-transformed fungicide concentration.

[0032] [Table 1]

[0033] As mentioned above, the E.C. 50 Values were determined by fitting a regression line of log-transformed percentage inhibition plotted against log-transformed fungicide concentration. EC 50 The lower the value, the more active it is. EC 50 The values show that pydiflumetofen provides very high activity against Ustilaginoidea virens (rice mildew).

[0034] Example 2 - In vitro activity of pydiflumetofen and other active ingredients commonly used for the control of rice mildew (caused by Ustilaginoidea virens) Using the same protocol as in Example 1 (above), the activity of pydiflumetofen against rice mildew was compared with the activity of other fungicidal active ingredients.

[0035] [Table 2]

[0036] EC 50 Values were determined by fitting a regression line of log-transformed percentage inhibition plotted against log-transformed fungicide concentration. EC 50 The lower the value, the more active it is. EC of 0.0045 ppm 50 The values show that pydiflumetofen offers significantly higher activity against Ustilaginoidea virens (rice mildew) compared to fungicides commonly used to treat rice mildew.

[0037] Example 3 - Efficacy of pydiflumetofen in the field 38 days after application Application method: Foliar spraying Water amount: 450L / ha Number of applications: 1 Application timing: BBCH 45-47

[0038] [Table 3]

[0039] A scale / index of 0 to 9 was used to define the level of disease severity, where 0 represents a healthy plant and 9 represents a high level of disease / severe symptoms. Each plant was graded on this 0 to 9 scale and the disease index was calculated using the following formula: Disease index (DI)= [Total (class frequency of evaluation class × score)] / [(total number of plants) × (maximum disease index)] × 100.

[0040] The above results show that pydiflumetofen provides good control against rice mildew in the field when used at lower doses (60-75 gai / ha) compared to the industry standard of trifloxystrobin plus tebuconazole used at a higher dose of 180 gai / ha.

[0041] Example 4 - Efficacy of pydiflumetofen in the field 77 days after application Application method: Foliar spraying Water amount: 450L / ha Number of applications: 1 Application timing: BBCH 45-47

[0042] [Table 4]

[0043] The above results show that pydiflumetofen provides good control of rice false mildew in the field when used at a low dose (75 gai / ha) compared to fungicides currently used to control rice false mildew, even 77 days after application.

Claims

1. 1. A method for controlling Ustilaginoidea virens in rice plants, the method comprising applying to the plant, plant part, or its habitat an effective amount of pydiflumetofen.

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

3. 3. The method of claim 1 or 2, wherein pydiflumetofen is applied during the early to mid-booting stage of rice plant growth.

4. 4. The method according to any one of claims 1 to 3, wherein pydiflumetofen is applied to the rice plants during BBCH growth stages 41 to 49.

5. 5. The method according to any one of claims 1 to 4, wherein pydiflumetofen is applied to the rice plants during the BBCH growth stage 45 to 47.

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

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

8. 8. The method according to any one of claims 1 to 7, wherein pydiflumetofen is applied to the plant, plant part or its habitat in an amount of from 60g per hectare to 75g per hectare.

9. 1. Use of pydiflumetofen, or an agrochemically acceptable salt, isomer, stereoisomer, diastereoisomer, enantiomer or tautomer thereof, for controlling Ustilaginoidea virens in rice plants.

Images