New application of pydiflumetofen

Abstract

The present invention relates to the use of N-methoxy (phenylethyl)-pyrazole carboxamides for controlling phytopathogenic diseases, in particular phytopathogenic fungi, of useful plants, and to a method for 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-pyrazol-4-carboxamide (fluxapyroxad) for the control of Ustilaginoidea species, in particular Ustilaginoidea virens, on rice plants, and to the use of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2, 4, 6-trichloro-phenyl) ethyl]-1H-pyrazol-4-carboxamide.

Description

[0001] The present invention relates to the use of N-methoxy(phenylethyl)-pyrazolecarboxamides for controlling phytopathogenic diseases of useful plants, in particular phytopathogenic fungi, and to methods for 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 (fluopicolide) for controlling Ustilaginoidea spp., in particular Ustilaginoidea virens, on rice plants.

[0002] Certain pyrazolylcarboxamide derivatives are known from WO 2008 / 148570, WO 2010 / 063700, WO 2010 / 084078 and WO 2008 / 151828 to have biological activity against phytopathogenic fungi.On the other hand, various fungicidal compounds of different chemical classes are known as botanical fungicides for use in various crops of cultivated plants.

[0003] U.S. smut fungus is a plant pathogen that causes the disease "smut" of rice, which is known to reduce grain yield and grain quality. Smut mainly affects quality because the fungus produces brown "smut balls" that contaminate rice grains at harvest, i.e. the pathogen converts individual grains of the rice ear into smut balls, the surface of which is covered with powdery chlamydospores during maturation. These balls are unsightly and if there are many of them in a load, they must be removed before the rice is used. It can also cause problems for exporting rice.

[0004] U.S. smut has a unique life cycle; white hyphae are produced by the fungus after it initially infects the floral organs of the rice crop. Over time, the infection matures and dark brown-green chlamydospores are produced on the rice spikelets. In addition, sclerotia may appear in the late fall. During its life cycle, U.S. smut goes through a sexual (ascospore) stage as well as an asexual (chlamydospore) stage. Chlamydospores are the main living structures and they can survive in the soil for up to four months. The additional formation of sclerotia allows the U.S. smut to survive longer, almost up to a year. These sclerotia can be present above or below the soil surface, which mature to form ascocarps (fruiting bodies). The ascospores of these fruiting bodies serve as the main source of infection that spreads the disease throughout the rice field. The disease is most severe when environmental conditions such as high humidity (above 80%) and temperatures ranging from 25°C to 30°C prevail. Late sowing of rice plants, high soil fertility, and large amounts of fertilizer 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 false smut.

[0006] 3-(Difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide (known by its common name "fluopicolide"), 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 within the class of succinate dehydrogenase inhibitors (SDHIs).

[0007] The present invention is based on the surprising discovery that pentocyclan also exhibits high levels of activity against U. oryzae spp. in rice plants.

[0008] Thus, in a first aspect, the present invention relates to a method of controlling U. oryzae var. oryzae in rice plants, the method comprising applying to the plant, plant part or the locus thereof an effective amount of pentocyclanil.

[0009] In another aspect, a method of controlling U. oryzae var. oryzae on a rice plant is provided, the method comprising applying to the plant, plant part, or the locus thereof, an effective amount of a composition comprising pentoquinoline.

[0010] In a further aspect, there is provided use of pentoquinoline or an agrochemically acceptable salt, isomer, stereoisomer, diastereomer, enantiomer or tautomer thereof for controlling U.S. smut fungus.

[0011] Fluopicolide and its preparation are described in WO 2010 / 063700, WO 2013 / 127764 and WO 2014 / 206855. The skilled person will appreciate 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 inhibit phytopathogenic 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, ISO name or as "the compound".

[0012] As used herein, the term "locus" means a place where or on which plants grow, or where seeds of cultivated plants are sown, or where seeds are to be placed in the soil. It includes soil, seeds, and seedlings, together with established vegetation.

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

[0014] As used herein, the term "plant propagation material" should be understood to mean the reproductive parts of useful plants, such as seeds, which can be used for the propagation of the useful plants, and vegetative materials, such as cuttings or tubers (e.g., potatoes). For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, corms, rhizomes and plant parts can be mentioned. Germinated plants and young plants that will be transplanted after germination or after emergence can also be mentioned. These young plants can be protected before transplanting by being treated completely or partially by dipping in a compound. Preferably, "plant propagation material" should be understood to mean seeds and / or roots, more preferably seeds.

[0015] The term "reproductive growth stage" refers to the final stage of plant growth following germination and vegetative growth. During the reproductive growth stage, the plant's energy is directed toward the production of flowers, fruits, and seeds. Several growth stages help identify key time periods in the life cycle of a rice crop. They are generally divided into stages that are primarily associated with vegetative or reproductive development. The vegetative period occurs first and is associated with a period of six to eight weeks after planting. The reproductive period is next and is generally associated with the formation, development, and maturation of the ear and kernels. Ear differentiation is the first stage of the reproductive growth period.

[0016] The reproductive growth stage typically begins at the onset of stem elongation (BBCH 30). In rice, the reproductive growth stage includes panicle differentiation (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). In wheat, the reproductive growth stage includes first node formation (BBCH 31), flag leaf formation (BBCH 37), booting (BBCH 41-49) and heading (BBCH 50-59).

[0017] The developing ear is microscopic in size inside the stem, and ear differentiation can be generally associated with the beginning of stem internode formation. When the internode elongation phase begins, chlorophyll accumulation occurs between the nodes to be separated in the process of forming the first stem internode between them. This accumulation of chlorophyll imparts a green color, which surrounds the developing internode, producing a green ring or band. Therefore, the internode elongation phase is sometimes referred to as the green ring phase. This phase is also referred to as the first green ring, because the additional internodes formed at the top of the first internode can also have a green ring effect when they begin to form. A total of five internodes can be produced in the formation of rice stems. As internode and ear formation continue, the ear differentiation phase occurs. Ear differentiation is the first stage of the reproductive period, when the newly formed ear becomes visible. At this stage, the ear in the stem has grown to about 1 / 8 inch. In the metric system, the length is about 2 millimeters, and this stage is sometimes referred to as the 2mm ear stage. The ear continues to grow and develop in the stem. In fact, the growth stage is called booting and is identified by the length of the ear. When the ear length reaches 2 inches, the growth stage is early booting. Mid-booting and late-booting occur when the ear is 2 to 5 inches and 5 inches or longer in length, respectively. Until now, identifying the growth stage during the reproductive period required dissection (splitting in half) of the stem. During the late-booting period, the ear is fully developed and the subsequent growth stage occurs after the ear is exposed and visible outside the stem. The heading stage is indicated when a portion of the ear is observed growing out of the end of the rice stem. From this point on, the growth stage is based on the status of the ear outside the rice stem. The heading stage is determined as a percentage, with the 50% heading stage occurring when 50% of the rice stems are heading or have headed (the ear has fully emerged from the stem).

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

[0019] For controlling U. oryzae , pentocyclan is applied or administered in an "effective amount," which means any amount of pentocyclan that is sufficient to achieve the desired level of control of U. oryzae after appropriate application.

[0020] Fluopicolide for controlling U.S. smut fungus can be used in unmodified form or preferably together with carriers and adjuvants conventionally used in the field of formulations and, for example, previously described in WO 2010 / 063700. Typically, when used for fungal control, fluopicolide is applied to useful plants by foliar application. However, for the control of U.S. smut fungus, the preferred method of application is direct application to the plant, the locus of the plant (e.g., soil) or direct application to plant propagation materials (e.g., application to seeds).

[0021] In another embodiment, fluopicolide is applied to the plant, plant part, or the locus thereof in the form of a fungicidal formulation. The formulation may contain one or more other desired components, including but not limited to liquid diluents, binders that serve as a matrix for the compounds as described herein, fillers for protecting seeds, and plasticizers for improving the flexibility, adhesion, and / or spreadability of the coating.

[0022] Fungicidal formulations, for example compositions comprising pentocyclamide and, if desired, solid or liquid adjuvants or monomers for encapsulating the compound, can 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).

[0023] Typical application rates per hectare are generally 1g to 2000g of fluopicolide per hectare, particularly 10g to 1000g / ha, preferably 10 to 800g / ha, more preferably 20g to 600g / ha, and most preferably 40g to 500g / ha. In particular, fluopicolide is applied with 40g to 400g active ingredient per hectare. In one embodiment, fluopicolide is applied with 50g to 100g active ingredient per hectare. In one embodiment, fluopicolide is applied with 60g to 75g active ingredient per hectare. When used to process seeds or as a leaching agent, a convenient application rate is from 1mg to 50g active substance per kg seed, preferably from 10mg to 30g active substance per kg seed, and more preferably from 10mg to 1g active substance per kg seed.

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

[0025] The composition of the present invention can be used in any conventional form, for example in the form of a twin pack, a dry powder for 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 suspoemulsion (SE), a capsule suspension (CS), a water-dispersible granule (WG), an emulsifiable granule (EG), an oil-in-water emulsion (EO), an oil-in-water emulsion (EW), a microemulsion (ME), a dispersible oil suspension (OD), an oil suspension (OF), an oil-soluble liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with an agriculturally acceptable adjuvant.

[0026] Such compositions can be produced in a conventional manner, for example by mixing active ingredients with appropriate formulation inerts (diluents, solvents, fillers and optionally other formulation ingredients, such as surfactants, biocides, antifreeze agents, adhesives, thickeners and compounds providing auxiliary effects). Conventional slow-release formulations intended to last for a long time can also be used. In particular, formulations to be applied in a spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders and granules may contain surfactants such as wetting agents and dispersants and other compounds providing auxiliary effects, such as condensation products of formaldehyde with naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0027] Typically, the formulation comprises from 0.01% to 90% by weight of active ingredient, from 0 to 20% of agriculturally acceptable surfactant and 10% to 99.99% of solid or liquid formulation inerts and one or more adjuvants, the active agent being composed of at least fluopicolide together with components (B) and (C), and optionally other active agents (particularly microbicides or preservatives or the like). Concentrated forms of the composition typically contain between about 2% and 80% by weight, preferably between about 5% and 70% of active agent. The application form of the formulation may, for example, contain from 0.01% to 20% by weight, preferably from 0.01% to 5% by weight of active agent. However, commercial products will preferably be formulated as concentrates, and end users will generally use diluted formulations.

[0028] Fluopicolide can be the sole active ingredient of the composition, or it can be mixed with one or more additional active ingredients (such as pesticides, fungicides, synergists, herbicides or plant growth regulators) as appropriate. In some cases, the additional active ingredients can produce unexpected synergistic activity.

[0029] Examples of suitable additional active ingredients include compounds selected from the group consisting of petroleum, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenylbenzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenylphenyl sulfone, acetothionil, aldicarb, sirox, fomanphos, fenthion, fenthion hydrogen oxalate, amitraz, cypermethrin, arsenic trioxide, azobenzene, azophos, benomyl, benoxafos, benzyl alcohol, benzophenone ... Benzyl formate, bixafen, bromethrin, bromophenazone, bromothion, bromophos, bromopyralid, buprofezin, butanone carbendazim, butanone sulfone carbendazim, butyl pyridaben, calcium polysulfide, octachlorocamphene, chlormethoxam, trithion, cypermethrin, cypermethrin, cypermethrin, cypermethrin hydrochloride, cypermethrin, cypermethrin, cypermethrin hydrochloride, chlorpyrifos, chlorpyrifos, ethyl chlorpyrifos, chlorpyrifos (chloromebuform), chlorpyrifos urea, propyl chlorpyrifos, chlorpyrifos, cypermethrin I, cypermethrin II, cypermethrin, closantel, coumaphos, cloro Mitong, Baclofos, Thiochlor, Fruitworm, DCPM, DDT, Demeton, Demeton-O, Demeton-S, Demeton-methyl, Demeton-O, Demeton-O-methyl, Demeton-S, Demeton-S-methyl, Demeton-S-methyl, Demeton-S-methyl, Bacteriostatic, Dichlorvos, Dicliphos, Dichlorvos, Dimethoate, Dimethoate, Dinex, Dinex-diclexine 、Dinocarb-4、Dinocarb-6、Oxydimethoate、Nitropentyl、Nitrooctyl、Nitrobutyl、Dinothion、Sulfondiphenyl、Disulfuron、DNOC、Dofenapyn、Doramectin、Indoxorb、Eprinomectin、Ethiothion、Ethiothion、Anti-mite、Fenbutatin、Fenthiocarb、Fenpyrad、Fenpyrad、Amifenpyrazone、Amifenpyrazone、Fentrifanil、Fentrimex、Fentrimex uron、Fentrimex、FMC 1137, fenthiocarb, fenthiocarb hydrochloride, formparanate, γ-HCH, chloranil, benzyl chloranil, hexadecyl cyclopropane carboxylate, isothiocarb, jasmonate I, jasmonate II, iodine, lindane, propanil, cypermethrin, dithiophos, methylthiophene, cypermethrin, methyl bromide, cypermethrin, chloranil, milbemid, propylamine, monocrotophos, malathion, moxidectin, naled, 4-chloro-2-(2-chloro-2-methyl- propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, fluazifop, nikkomycin, pentocyanamide, pentocyanamide 1:1 zinc chloride complex, omethoate, isothiocarb, sulfone, pp'-DDT, parathion, permethrin, fenthion, phosalone, thiocyanate, phosphamidon, polychloroterpenes, polynactins, chloranil, cypermethrin, propoxur, ethidium, phosphamidon,Pyrethrin I, Pyrethrin II, Pyrethrin, Pyrithiophos, Pyrithiophos, Quinalphos, Quintiofos, R-1492, Glyphosate, Rotenone, Octaphos, Clemath, Selamectin, Threonine, SSI-121, Sufilam, Sulfluramid, Sultop, Sulphur, Flumethoxine, τ-Fluvalinate, TEPP, Terbutal, Tetrachlorobenzene Sulfonate, Thiafenox, Antimicrobial, Long-lasting Wei, Methyl Disulfothion, Cypermethrin, Sulimex, Vibriophos, Fenamiphos, Triazophos, Triazuron, Triclofos, Triacin, Vaniliprole, Bethoxazin, Copper Dioctanoate, Copper Sulfate, Ciprofloxacin yne), dichloronaphthoquinone, dichlorophen, endosin, triphenyltin, slaked lime, mancozeb, quinone, quinone, simazine, triphenyltin acetate, triphenyltin hydroxide, fusulin, piperazine, thiophanate, chloralose, fenthion, pyridine-4-amine, strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxalin-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, dispyrithione, dodesine, sodium sulfone, formaldehyde, mercurygafen, kasugamycin, kasugamycin hydrochloride hydrate, nickel di(dimethyldithiocarbamate), trichloromethylpyridine, octhilone, oxolinic acid, oxytetracycline, hydroxyquinoline potassium sulfate, thiabendazole, streptomycin, streptomycin sesquisulfate, chloranthate, thimerosal, cotton brown banded tormentor GV, radiobacterium, Amblyseius species (Amblyseius spp.), celery armyworm NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletesaphidimyza, Spodoptera exigua NPV, Bacillus sphaericus Neide, Beauveria brongniartii, Chrysoperla carnea, Cryptolaemus montrouzieri, Codling moth GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Heterorhabditis bacteriophora) and Heterorhabditis megidis,Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus, Cabbage armyworm NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, Neodiprionsertifer NPV and N. lecontei NPV, species of the genus Pseudomonas, Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae), Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernemas spp., Trichogramma spp., Typhlodromus occidentalis, Verticillium lecanii, apholate, bisazir, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl apholate apholate), morzid, penfluron, tepa, thiohempa, thiohempa, trothamide, urethaneimide, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol, (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)-eicos-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)-Dodec-7,9-dien-1-yl acetate, (9Z,11E)-Tetradec-9,11-dien-1-yl acetate, (9Z,12E)-Tetradec-9,12-dien-1-yl acetate, 14-methyloctadec-1-ene, 4-methylnon-5-ol and 4-methylnon-5-one, α-polystyrene, western pine beetle aggregation pheromone, codlelure, codlemone, cuelure, epoxide nonadecane, dodec-8-en-1-yl acetate, dodec-9-en-1-yl acetate ester, dodeca-8,10-dien-1-yl acetate, dominicalure, ethyl 4-methyloctanoate, eugenol, southern pine beetle aggregation pheromone (frontalin), grandlure, grandlure I, grandlure II, grandlure III, grandlure IV, hexalure, ipsdienol, ipsenol, japonilure, lineatin, litlure, looplure, medlure, megatomoic acid acid), methyleugenol, muscalure, octadecane-2,13-diene-1-yl acetate, octadecane-3,13-diene-1-yl acetate, orfralure, oryctalure, ostramone, siglure, sordidin, sulcatol, tetradecane-11-ene-1-yl acetate, trimedlure, trimedlure A, trimedlure B1, trimedlure B2, trimedlure C, trunc-call, 2-(octylthio)ethanol, butopyronoxyl, butoxy(polypropylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, DEET, dimethyl carbate), dimethyl phthalate, ethyl hexanediol, hexamide, methoquin-butyl, methylneodecanamide, oxamate, picaridin,1-Dichloro-1-nitroethane, 1,1-dichloro-2,2-di(4-ethylphenyl)ethane, 1,2-dichloropropane and 1,3-dichloropropylene, 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 dimethylcarbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenylmethylcarbamate Ester, 2-(4-chloro-3,5-xylyloxy)ethanol, 2-chlorovinyl diethyl phosphate, 2-imidazolidinone, 2-isovaleryl indan-1,3-dione, 2-methyl (prop-2-ynyl) aminophenyl methylcarbamate, 2-thiocyanatoethyl laurate, 3-bromo-1-chloroprop-1-ene, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate, 4-methyl (prop-2-ynyl) amino-3,5-xylyl methylcarbamate, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate, athiathio Phosphorus, acrylonitrile, chloromethyl naphthalene, alomycin, chlorpyrifos, α-decandrin, aluminum phosphide, chlorpyrifos, neonicotinoids, ethyl thiocarb (athidathion), methyl pyrifos, Bacillus thuringiensis delta-endotoxin, barium hexafluorosilicate, barium polysulfide, fumonisin, Bayer 22 / 190, Bayer 22408, β-cyfluthrin, β-cypermethrin, bioethanomethrin, biopermethrin, bis (2-chloroethyl) ether, borax, bromophenone, bromo-DDT, chlorpyrifos, chlorpyrifos, termidorphine (b utathiofos), butyl phosphate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, badan hydrochloride, cevadine, borneol, chlordane, chlordecone, chloroform, chloropicrin, chloraniloxime, chlorprazophos, cis-resmethrin, cismethrin, clocythrin, copper acetoarsenite, copper arsenate, copper oleate, coumithoate, cryolite, CS 708, benzonitrile, cypermethrin, cypermethrin, d-methanthrin, DAEP, dazomethane, decarbofuran, diamidafos, isochlor, dimethoate, dicresyl, cypermethrin, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dior, tetrafluthrin, demicarb, pyrethrin, methyl chlorpyrifos, difenocarb, propanol, pentotropol, dinofuranoside, fenthion, vegetable phosphorus, thiopyraphos, DSP, ecdysterone, EI 1642, EMPC, EPBP, etaphos, ethiofencarb,Ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, EXD, fenthion, ethylbenzene, fenthion, fenoxacrim, cypermethrin, fenthion, ethylfenthion, flucofuron, butylfenthion, phosphoarsenic acid ester, butylfenthion, furathiocarb, pyrethroid, biguanide salt, biguanide acetate, sodium tetrathiocarbonate, benzyl chlorpyrifos, HCH, HEOD, heptachlor, cypermethrin, HHDN, hydrogen cyanide, quinolincarb, IPSP, chlorfenapyr, carbofuran, isodrin, isofenphos, transplanting spirit, rice blast, oxathion, juvenile hormone I, juvenile hormone II, juvenile hormone III, chlorfenapyr, methoprene, lead arsenate, bromophenylphos, acetamiprid, thiamethoxam, m-isopropyl methyl carbamate, magnesium phosphide, azide Phosphorus, methyl aphid, chlorpyrifos, mercurous chloride, methyl sulfoxide, metamphos, metamphos potassium, metamphos sodium, methyl sulfonyl fluoride, butenamidophos, methoprene, methyl ether thiocyanate, methoxychlor, methyl isothiocyanate, methyl chloroform, dichloromethane, oxathione, anthelmintic, naphthiophos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, orthonicotine, O-5-dichloro-4-iodophenyl O-ethylethyl phosphonothioate, O,O-diethyl O-4-methyl-2-oxo-2H-benzopyran-7-ylphosphonothioate, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-ylphosphonothioate, O,O,O',O'-tetrapropyl dithiodipyrophosphate, oleic acid, p-dichlorobenzene, methyl parathion, pentachlorophenol, pentachlorophenyl laurate, PH 60-38, fenthion, parachlorothion, phosphine, methyl phoxim, methamidophos, polychlorinated dicyclopentadiene isomers, potassium arsenite, potassium thiocyanate, precocious element I, precocious element II, precocious element III, amidophos, profluthrin, fenthion, pyraclostrobin, anti-pyrethroid, quassia, quinalphos-methyl, fenthion, iodophos, resmethrin, rotenone, thiamethoxam, ryanodine, sabadilla, octamidine, clostridium, SI-0009, thiamethoxam, sodium arsenite, sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenol, sodium selenate, sodium thiocyanate, sulcofuron, Sulcofuron-sodium, sulfuryl fluoride, thiopromide, tar, thiabendazole, TDE, butylpyrimidinphos, bispyribophos, cyclopentylthrin, tetrachloroethane, thiochlorvos, cyclohexane, cyclohexane oxalate, cypermethrin, cypermethrin monosodium, tralomethrin, trans-permethrin, trichlormetaphos-3, chlorpyrifos, tolprocarb, chlorpyrifos-butyl, methoprene, veratridine, veratridine, XMC, zetamethrin, zinc phosphide, tolfenphos, chlorfluanid, tetrafluanid, bis(tributyltin)oxide, bromoacetamide,Ferric phosphate, niclosamide-ethanolamine, tributyltin oxide, pyromorph, snail killer, 1,2-dibromo-3-chloropropane, 1,3-dichloropropylene, 3,4-dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-1,3,5-thiadiazin-3-yl acetic acid, 6-isopentenylaminopurine, anisin, benclothiaz, cytokinin, DCIP, furfural, isamidophos, kinetin, verrucosporium mycorrhizal composition, tetrachlorothiophene, xylenol, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, Reynoutria sachalinensis) extract, α-chloroalcohol, antu, barium carbonate, bifenthion, brodifacoum, brodifacoum, brofenthion, chlorfenthion, cholecalciferol, chlorfenthion, chlorfenthion, chlorfenthion, chlorfenthion, chlorfenthion, calciferol, flufenthion, fluoroacetamide, flufenthion, flufenthion hydrochloride, flufenthion, chlorfenthion, phosphorus, flufenthion, chlorfenthion, chlorfenthion, sciline glycoside, sodium fluoroacetate, thallium sulfate, warfarin, 2-(2-butoxyethoxy) ethyl piperate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol with nerolidol, synergistic acetylenic ether, MGK 264, synergistic ether, synergistic aldehyde, synergistic ester (propyl isomer), S421, enhanced powder, sesasmolin, sulfoxide, anthraquinone, copper cyclohexane, copper oxychloride, dicyclopentadiene, serene, zinc cyclohexane, zinc thiamide, imanin, ribavirin, chloroindole hydrazide, mercuric oxide, methyl thiophanate, azaconazole, bifenthionol, fumarole, cyproconazole, difenoconazole, diniconazole, fluepiconazole, nitrobenzazole, fluquinconazole, flusilazole, flutriafol, furopyram, hexaconazole, imazalil, imipenem, cyproconazole, metconazole, myclobutrazol, paclobutrazol, rice blast ester, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyraclostrobin, tebuconazole, flufenoxazole, triadimefon, triadimenol, triflumizole, trichlorfonazole, chlorfenapyr, flufenamic acid, bupirimate, dimethirimol, ethirimol, dodecacyclic morpholine, fenpropidin, fenpropimorph, spiroxaplanol, tridecamorph, cyprodinil, pyraclostrobin, pyrimethanil, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, furamide, oxadixyl, carbendazim, debacarb, thiabendazole, chlozolinate, dichlozoline,Myclozoline, procymidone, vinclozoline, boscalid, carboxin, procymidone, flutolanil, flutolanil, oxacarb, penthiopyrad, thiofuran, dodine, biguanide, azoxystrobin, ethersstrobin, enestrobin, enestrobin, flutolanil, fluoxastrobin, ethersstrobin, fenoxystrobin, trifloxystrobin, trifloxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, ferram, mancozeb, maneb, manam, methyl propineb, maneb, captafol, captan, pyraclostrobin, folpet, tolylfluanid, Bordeaux mixture, copper oxide oxide), mancopper, oxine-copper, nitrothal-isopropyl, kefansan, iprobenphos, phosdiphen, tolclofos-methyl, dichlorvos, benzathiapiprolin, blasticidin-S, chloroneb, chlorothalonil, cyfluanid, cymoxanil, diclocymet, diclomezine, dicloran, diethofencarb, oxadiazine, flumorph, dithianon, ethaboxam, etridiazole, fenamidone, fenamidone, fenoxanil, ferimazole mzone), fluazinam, flumetylsulforim, fluopicolide, fluoxytioconazole, flusulfamide, fluoxazolidinone, fosetyl-aluminium, hymexazol, propineb, cyazofamid, methasulfocarb, mefenoxam, pencycuron, phthalide, polyoxins, propamocarb, pyraclostrobin, proquinazid, pyroquilon, pyriofenone, quinoxyfen, pentachloronitrobenzene, thiazolamide, triazoxide, tricyclazole, triazine, validamycin, valeramide, zoxamide,mandipropamid, fluphenazine, isopyrazam, sedaxane, benzovinflumizone, fluopyrazol, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, isoflucyclamide, isothiocyanate, dipymetitrone, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, 4-( 2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-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, fluinoxam, jiaxiangjunzhi, ribonucleic acid, dichlorobenzyl, 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, oxathiapiprolin, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridinyl]carbamate, pyraziflumid, inpyrfluxam, trolprocarb, chlorfenapyr, ipfentrifluconazole, 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-piperidinyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl] methanesulfonate, N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridinyl]carbamic acid but-3-ynyl ester,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, pyridachlometyl chloride, 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, aminopyridine rifen), azopyrafenib, indazolesulfazopyrafenib, fluopicolide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine, fluobosaccharide, fenpicoxamid, methylpyridine oxime, isobutylethoxyquinoline, ifofenquin, quifumarin, isoprene, 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylic acid ethyl ester (which can be prepared by the method described in WO2020 / 056090), 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enyloxy]phenyl]methyl]pyrazole-3-carboxylic acid ethyl ester (which can be prepared by 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 (can be prepared by the method described in WO 2020 / 097012), methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (can be prepared by the method described in WO 2020 / 097012), methyl 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (can be prepared by the method described in WO 2020 / 109391), 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (can be prepared by 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 (can be prepared by 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, benzathiostrobin, cyanobacterium methyl, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1), fluopyram, flufenamid, fluthiazolin, fluopyram, pyriproxyfen, picarbutrazol ox), 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]oxy]benzonitrile, methyl tetraproline, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide )-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-diphenyl]-4-yl]-5-pyrimidinemethanol, fluxaproline, enoxastrobin, (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoic acid methyl ester, (Z)-3-methoxy-2-[2-methyl-5-(4- propyltriazol-2-yl)phenoxy]prop-2-enoic acid methyl ester, (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoic acid methyl ester, (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoic acid methyl ester, (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoic acid methyl ester (these compounds can be prepared from WO 2020 / 079111), (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester, (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (these compounds can be prepared by the method described in WO 2020 / 193387), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 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, trinexapac-ethyl, syringoxystrobin, zhongshengmycin, thiophanate-copper, thiophanate-zinc, amitolin, iprodione, cinclorac, 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 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-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 can be prepared from WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridinyl]-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 by the method described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetane-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 by 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-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]-7,8-difluoro-quinoline-3-carboxamide, 8-fluoro-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 [(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 by 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, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds can be prepared by 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 by 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]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine (these compounds can be prepared from WO 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared by 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 by the method 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 by the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared by the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared by the method described in WO 2016 / 156290); 2-amino-6-methyl-pyridine-3-carboxylic acid (4-phenoxyphenyl) methyl ester (this compound can be prepared by the method described in WO 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']bipyrrole-1,3,5,7(2H,6H)-tetraone (this compound can be prepared by the method described in WO 2011 / 138281),N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenethiocarboxamide; 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 by 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 by the method described in WO 2-(Difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared by 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 by the method described in WO 2014 / 095675); 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared by the method described in WO2018 / 065414); 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester (this compound can be prepared by the method described in WO 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-carbonimide]-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 invention will now be described with reference to the following examples, which are illustrative and do not limit the scope of the invention in any way. The following examples demonstrate the ability of pentoquinoline to control U.S. smut fungus.

[0031] Biological Examples

[0032] Example 1 - In vitro activity of pentoquinoline against rice false smut (caused by U. oryzae oryzae) by mycelial growth method

[0033] U. oryzae (the pathogen causing rice false smut) 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 were prepared at the edge of the colonies by a 5 mm diameter borer. Fluopicolide was dissolved in dimethyl sulfoxide (DMSO) to give 4 x 10 4 μg / mL stock solution. PSA medium was mixed with the stock solution of fluopicolide to obtain different series of concentrations: 0, 0.0005, 0.0010, 0.0025, 0.0040, 0.0055 and 0.007 μg / mL. Using the hyphal growth method, mycelial plugs were transferred to the center of PSA medium plates containing different fluopicolide concentrations. After 14 days of incubation in a 28°C incubator, the diameter of each hyphal colony on the PSA plate was measured and the inhibition rate was calculated. EC 50 Values ​​were determined by fitting regression lines plotting the log-transformed percent inhibition versus the log-transformed fungicide concentration.

[0034] Table 1 - In vitro activity of pentozolin against rice false smut (caused by U.S. smut fungus)

[0035]

[0036]

[0037] As mentioned above, EC 50 Values ​​were determined by fitting regression lines plotting log-transformed percent inhibition versus log-transformed fungicide concentration. EC 50 The lower the value, the higher the activity. 50 The value of 0.0037 μg / mL indicated that pentoquinol provided very high activity against U. oryzae oryzae (rice false smut disease).

[0038] Example 2 - In vitro activity of pentoquinoline and other active ingredients commonly used to control rice false smut (caused by U. oryzae )

[0039] Using the same protocol as in Example 1 (above), the activity of pentoquinoline against rice false smut was compared with the activity of other fungicidal active ingredients.

[0040] Table 2 - In vitro activity of pentoquinoline and other active ingredients commonly used to control rice false smut (caused by U. oryzae oryzae)

[0041]

[0042]

[0043] EC 50 Values ​​were determined by fitting regression lines plotting log-transformed percent inhibition versus log-transformed fungicide concentration. EC 50 The lower the value, the higher the activity. 50 The value of 0.0045 ppm indicates that pentocyclan provides very high activity against U. oryzae oryzae (rice false smut) compared to fungicides commonly used to treat rice false smut.

[0044] Example 3 - Efficacy of pentocyclanil in the field 38 days after application

[0045] Application method: Foliar spray

[0046] Water volume: 450L / ha

[0047] Number of applications: 1

[0048] Application time: BBCH 45-47

[0049] Table 3 - Field test results 38 days after application

[0050]

[0051] The level of disease severity is defined using a scale / index from 0 to 9, where 0 represents a healthy plant and 9 represents a high level / severe symptoms of the disease. Each plant is graded on this 0 to 9 scale and the disease index is calculated using the following formula:

[0052] Disease index (DI) =

[0053] [Sum (category frequency x score of rating category)] / [(total number of plants) x (maximum disease index)] x 100.

[0054] The above results show that fluopicolide provided good control of rice false smut in the field when used at a lower dosage rate (60-75 gai / ha) compared to the industry standard trifloxystrobin + tebuconazole used at a higher dosage rate (180 gai / ha).

[0055] Example 4 - Efficacy of pentocyclanil in the field 77 days after application

[0056] Application method: Foliar spray

[0057] Water volume: 450L / ha

[0058] Number of applications: 1

[0059] Application time: BBCH 45-47

[0060] Table 4 - Field test results 77 days after application

[0061]

[0062] The above results indicate that pentocyclan provides good control of rice false smut in the field, even 77 days after application, when used at a low dosage rate (75 gai / ha) compared to the fungicides currently used to control rice false smut.

Claims

1. A method for controlling U.S. smut fungus on rice plants, the method comprising applying an effective amount of pentoquinoline to the plant, plant part or the locus thereof.

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

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

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

5. The method according to any one of claims 1 to 4, wherein pentoquinol is applied during BBCH growth stages 45 to 47 of the rice plant.

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

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

8. A method according to any one of claims 1 to 7, wherein pentothiocarb is applied to the plant, plant part or the locus thereof in an amount of 60 g per hectare to 75 g per hectare.

9. Use of pentoquinoline or an agrochemically acceptable salt, isomer, stereoisomer, diastereomer, enantiomer or tautomer thereof for controlling U.S. smut fungus on rice plants.

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