Methods for controlling or suppressing plant pathogens

Abstract

The present invention relates to the use of N-methoxy(phenylethyl)-pyrazolecarboxamides for the control or suppression of plant pathogens, and compositions comprising such compounds. In particular, the present invention relates to the use of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide (pydiflumetofen) for the control or suppression of plant pathogens, and compositions comprising such compounds.

Description

[Technical field]

[0001] The present invention relates to the use of N-methoxy(phenylethyl)-pyrazolecarboxamides for the control or suppression of plant pathogens, and compositions comprising such compounds. In particular, the present invention relates to the use of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide (pydiflumetofen) for the control or suppression of plant pathogens, and compositions comprising such compounds. [Background technology]

[0002] Bacterial plant diseases caused by plant pathogens are of major concern to growers worldwide; they cause hormonal imbalances in the infected plants, which can lead to problems such as stunting, overgrowth, galling, root branching, defoliation, resetting, necrosis, tissue dissociation, wilting, reduced photosynthetic area, hyperplasia, and epiphytic leaf growth. These problems alter the nutrient levels of the affected plants at both qualitative and quantitative levels; and have adverse effects on the global food supply and economy. See Kannan et al., "Sustainable Approaches to Controlling Plant Pathogenic Bacteria".

[0003] Plant pathogens can be easily spread by several means, including water, wind, insects, animals, human activity, agricultural and tillage machinery (especially during the vegetative propagation of plants in seedbeds), and also through the soil.

[0004] The control or suppression of plant pathogens is mainly achieved by the prevention and elimination of plant pathogens. Currently, there are limited solutions for controlling or suppressing the activity of plant pathogens on plants. The main chemical controls include the use of copper-based products (often residual), agricultural antibiotics, and resistance inducers such as acibenzolar-S-methyl. Some fungicides used to control fungal diseases can have a suppressive effect on the disease even if they do not act directly on the plant pathogen. For example, some strobilurin fungicides can have a tonic effect on the plant and can induce a defense response (however, they often require multiple applications), but do not act directly on the plant pathogen itself. Summary of the Invention

[0005] The compound 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide (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 of the succinate dehydrogenase inhibitor (SDHI) class. The present invention is based on the surprising discovery that 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide also exhibits antibacterial activity and inhibitory effect, and can therefore now be used in the fight against plant pathogens and thus in the fight against plant bacterial diseases.

[0006] Thus, in a first aspect, the present invention relates to a method for controlling or suppressing phytopathogenic fungi on a useful plant, comprising applying to the plant, plant part or locus thereof an effective amount of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide.

[0007] In another aspect, there is provided a method for controlling or suppressing plant pathogens on a useful plant, the method comprising applying to the plant, plant part, or locus thereof an effective amount of a composition comprising 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide.

[0008] In a further aspect, there is provided the use of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide, or an agrochemically acceptable salt, isomer, stereoisomer, diastereoisomer, enantiomer or tautomer thereof, for controlling a plant bacterial disease.

[0009] Also provided is a method for controlling or inhibiting the effects of phytopathogenic fungi on useful plants, comprising applying to the plant, plant part, or locus thereof an effective amount of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide.

[0010] Further provided is a method for controlling or inhibiting the effects of phytopathogenic fungi on a useful plant, comprising applying to the plant, plant part, or locus thereof an effective amount of a composition comprising 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] 3-(Difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide and its preparation are described in WO 2010 / 063700, WO 2013 / 127764, and WO 2014 / 206855. Those skilled in the art will understand 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, individually or as racemates, can be used to control or suppress plant pathogens. This 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 may be referred to as "the compound."

[0012] As described herein, the present invention relates to a method for controlling or suppressing phytopathogenic fungi on useful plants, comprising the application of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide to the useful plant to be protected or to its locus in an amount effective to act on said phytopathogenic fungi. 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide can also be applied to plant propagation materials (e.g. seeds, cuttings, and seedlings).

[0013] Likewise, a method for controlling or suppressing the effects of phytopathogenic fungi on useful plants is described, which comprises the application of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide to the useful plant to be protected, or to the locus thereof, in an amount effective to act on the phytopathogenic fungi.

[0014] As used herein, the term "useful plants" typically includes plants of the following species: grapes; cereals, such as wheat, barley, rye, or oats; sugar beets, such as sugar beets, or fodder beets; fruits, such as pome fruits, stone fruits, or soft fruits, such as apples, pears, plums, peaches, almonds, walnuts, cherries, strawberries, raspberries, or blackberries; legumes, such as beans, lentils, peas, or soybeans; oil plants, such as rape, mustard, poppy, olive, sunflower, coconut, castor oil plants, cocoa beans, or groundnuts; cucumber plants, such as mallow, cucumber, or melon; fiber plants, such as cotton, hemp, cannabis. , or jute; citrus fruits, such as oranges, lemons, grapefruits, or mandarins; vegetables, such as rapeseed, spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, sweet potatoes, cucurbits, peppers, paprika, or herbs; Lauraceae, such as avocado, cinnamon, or camphor; rice; corn; tobacco; nuts; coffee; sugarcane; tea; vines; hops; durian; bananas; rubber plants; grass or ornamental plants, such as flowers, shrubs, broadleaf trees, or evergreen trees, such as conifers; ornamental crops, such as roses, geraniums, pelargoniums, impatiens, cyclamen, poinsettias, pansies, magnolias, or zinnias; bulbs, such as tulips. This above list does not represent any limitation.

[0015] As used herein, the term "plant pathogen" refers to a bacterium that causes disease in plants. Examples of plant pathogenic bacteria include, but are not limited to, Agrobacterium spp., Acidovorax spp., Arthrobacter spp., Burkholderia spp., Candidatus Liberibacter spp., Clavibacter spp., Clostridium spp., Corynebacterium spp., Dickeya spp., Erwinia spp., Leifsonia spp., Pantoea spp., and the like. spp.), Pectobacteriumm spp., Phytoplasma spp., Pseudomonas spp., Ralstonia spp., Rhizobacter spp., Rhizomonas spp., Rhodococcus spp., Serratia spp., Sphingomonas spp., Sprioplasma spp., Streptomyces spp., Xanthomonas spp., and Xylella spp.

[0016] The term "locus" as used herein means the field in which the plant is growing or the location where the seed of the cultivated plant is sown or where the seed is planted in the soil, including soil, seeds, and seedlings, as well as indigenous plants.

[0017] The term "plant" refers to all physical parts of a plant (eg, seeds, seedlings, roots, stems, petioles, and leaves).

[0018] The term "plant propagation material" as used herein is understood to refer to the reproductive parts (e.g. seeds) of useful plants that can be used for the propagation of this useful plant, and to plant material (e.g. cuttings or tubers, e.g. potatoes). For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, corms, rhizomes, and plant parts may be mentioned. Also included may be sprouted plants, and seedlings that are transplanted after sprouting or emerging from the soil. The seedlings may be protected before transplanting by total or partial treatment by immersion in a compound. Preferably, "plant propagation material" is understood to refer to seeds and / or roots, more preferably to seeds.

[0019] The term "fungicide" as used herein in reference to 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide means that the compound is capable of controlling or inhibiting plant pathogens.

[0020] To control or suppress plant pathogens, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide is applied or administered in an "effective amount", which means any amount of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide sufficient to achieve the desired level of control or suppression of plant pathogens upon suitable application.

[0021] The effectiveness of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide against plant pathogens can be evaluated, for example, by comparing the area of ​​damaged leaves in the case of Xanthomonas spp. Those skilled in the art are familiar with such methods, and further details of the various methods are given in the examples below.

[0022] The phrase "control or suppress the effects of plant pathogens" as used herein with respect to 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide means that the compound can reduce the incidence or severity of the effects that plant pathogens have on crops of useful plants. For example, in the case of Xanthomonas spp., preventing or reducing spot disease; and in the case of Agrobacterium spp., preventing club disease (i.e., preventing the formation of tumors). This list does not represent any limitation.

[0023] The compound 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide can be used to maintain plant health, and can be used therapeutically, preventively, or systematically to control or suppress plant pathogens. Controlling or suppressing plant pathogens can reduce damage to plants, and therefore can increase yields at the same time.

[0024] Examples of plant pathogenic fungi to which 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide can be applied include Agrobacterium spp., Acidovorax spp., Arthrobacter spp., Burkholderia spp., Candidatus Liberibacter spp., Clavibacter spp., Clostridium spp., Corynebacterium spp., Dickeya spp., spp., Erwinia spp., Leifsonia spp., Pantoea spp., Pectobacterium spp., Phytoplasma spp., Pseudomonas spp., Ralstonia spp., Rhizobacter spp., Rhizomonas spp., Rhodococcus spp., Serratia spp., Sphingomonas spp., Sprioplasma spp. spp.), Streptomyces spp., Xanthomonas spp., and Xylella spp.

[0025] In particular, examples of plant pathogenic fungi to which 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide can be applied include Agrobacterium spp., Candidatus Liberibacter spp., Clavibacter spp., Dickeya spp., Erwinia spp., Pectobacterium spp., Pseudomonas spp., Ralstonia spp., and Xanthomonas spp.

[0026] Preferably, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide can be applied to the following plant pathogens: Agrobacterium tumefaciens, Candidatus Liberibacter asiaticus, Clavibacter michiganensis, Clavibacter sepedonicus, Dickeya dadantil, Dickeya solani, Erwinia amylovora, amylovora, Pectobacterium atrospeticum, Pectobacterium carotovorum, Pseudomonas savastoni, Pseudomonas syringae, Ralstonia solanacearum, Xanthomonas axonopodis, Xanthomonas campestris, Xanthomonas oryzae, Xanthomonas perforans, and Xylella fastidiosa.

[0027] More preferably, the plant pathogenic fungi to which 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide can be applied include Agrobacterium tumefaciens, Dickeya dadantil, Dickeya solani, Erwinia amylovora, Pectobacterium atrospeticum, Pectobacterium carotovorum, Pseudomonas syringae, Ralstonia solanacearum, and the like. solanacearum, Xanthomonas axonopodis, Xanthomonas campestris, Xanthomonas oryzae, Xanthomonas perforans, and Xylella fastidiosa.

[0028] In one embodiment there is provided a method of controlling or inhibiting plant pathogens selected from Xanthomonas spp, Pseudomonas spp, Agrobacterium spp, Ralstonia spp, Clavibacter spp, and Xylella spp. Methods for controlling or suppressing the effect of phytopathogenic bacteria on useful plants are provided, wherein the phytopathogenic bacteria are selected from Xanthomonas spp., Pseudomonas spp., Agrobacterium spp., Ralstonia spp., Clavibacter spp., and Xylella spp.

[0029] In another embodiment, there is provided a method for controlling or inhibiting a plant pathogen selected from Agrobacterium spp., Pseudomonas spp., Ralstonia spp., and Xanthomonas spp. There is provided a method for controlling or inhibiting the effect of a plant pathogen on a useful plant, wherein the plant pathogen is selected from Agrobacterium spp., Pseudomonas spp., Ralstonia spp., and Xanthomonas spp.

[0030] As shown herein, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide is particularly effective against Agrobacterium spp., Pseudomonas syringae, Ralstonia spp., and Xanthomonas spp. Specifically, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide is particularly effective against Agrobacterium tumefaciens, Pseudomonas syringae, Xanthomonas perforans, Xanthomonas orycea, and Xanthomonas perforans and Xanthomonas campestris.

[0031] Useful plants in which 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide may be used include grapes; cereals, such as wheat, barley, rye, or oats; sugar beets, such as sugar beets, or fodder beets; fruits, such as pome fruits, stone fruits, or soft fruits, such as apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, or blackberries; legumes, such as beans, lentils, peas, or soybeans; oil plants, such as rapeseed, mustard, poppy, olives, sunflowers, coconuts, castor oil plants, cocoa beans, or groundnuts; cucumber plants, such as mallow, cucumbers, or melons; fiber plants, such as cotton, hemp, cannabis, or jute; citrus fruits, such as oranges, lemons, grapefruit, or mandarins; vegetables, such as rape, spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, sweet potatoes, cucurbits, chili peppers, paprika, or herbs; lauraceae, such as avocado, cinnamon, or camphor; rice; corn; tobacco; nuts; coffee; sugarcane; tea; vines; hops; durian; bananas; rubber plants; turf or ornamental plants, such as flowers, shrubs, broadleaf trees, or evergreen trees, such as conifers; ornamental crops, such as roses, geraniums, pelargoniums, impatiens, cyclamen, poinsettias, pansies, magnolias, or zinnias; bulbs, such as tulips.

[0032] Preferred useful plants that can use 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide include vegetables, fruits, grapes, rice, and ornamental plants.More preferred useful plants include tomatoes, geraniums, pelargoniums, magnolias, rice, and zinnias.

[0033] The compound 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide for controlling phytopathogenic fungi can be used in unmodified form or, preferably, together with carriers and adjuvants that are conventionally used in the field of formulation and have already been described, for example, in WO 2010 / 063700. Typically, when used for fungal control, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide is applied to useful plants by foliar application. However, to control phytopathogenic fungi, the preferred application method is direct to the plant, the location of this plant (e.g., soil) or indirect to plant propagation material (e.g., applied to seeds).

[0034] In a further embodiment, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide is applied to the plant, plant part, or locus thereof in the form of a fungicidal formulation, which may contain one or more other desired ingredients, including, but not limited to, liquid diluents, binders that act as a matrix for the compounds described herein, excipients to protect the seeds, and plasticizers to improve the flexibility, adhesion, and / or spreadability of the coating.

[0035] The present bactericidal formulations (e.g. compositions comprising 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide and, if desired, solid or liquid adjuvants or monomers for encapsulating the compound) can typically be prepared in known manner by mixing and / or grinding the compound with extenders, e.g. solvents, solid carriers, and optionally surface-active compounds (surfactants).

[0036] Typical application rates per hectare are generally 1g to 2000g of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide per hectare, specifically 10g to 1000g / ha, preferably 10 to 800g / ha, more preferably 20g to 600g / ha, and most preferably 40g to 500g / ha. Specifically, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide is applied at 40g to 400g of active ingredient per hectare. When used as a seed treatment or drenching agent, convenient application rates are from 1 mg to 50 g of active substance per kg of seed, preferably from 10 mg to 30 g of active substance per kg of seed, more preferably from 10 mg to 1 g of active substance per kg of seed.

[0037] The compositions of the present invention may be utilized in any convenient form, for example, twin packs, dry seed treatment powders (DS), seed treatment emulsions (ES), seed treatment flowable concentrates (FS), seed treatment nutrient 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 (W), and the like. The composition may be available in the form of a water-in-oil (EO), emulsifiable granules (EG), emulsions, water-in-oil (EO), emulsions, oil-in-water (EW), microemulsions (ME), oil dispersions (OD), oil-miscible fluids (OF), oil-miscible liquids (OL), soluble concentrates (SL), very low volume suspensions (SU), very low volume liquids (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0038] Such compositions can be prepared in a conventional manner, for example, by mixing the active ingredient with suitable formulation inert substances (diluents, solvents, excipients, and optionally other formulation ingredients, such as surfactants, biocides, antifreeze agents, tackifiers, thickeners, and compounds that provide adjuvant activity effects). Also, if long-term effectiveness is intended, conventional sustained release formulations can be utilized. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, and the like), wettable powders, and granules, can contain surfactants (e.g., wetting agents and dispersants), as well as other compounds that provide adjuvant activity effects (e.g., formaldehyde, naphthenesulfonates, alkylarylsulfonates, ligninsulfonates, fatty alkyl sulfates, and condensation products of ethoxylated alkylphenols and ethoxylated fatty alcohols).

[0039] In general, the formulations contain 0.01 to 90% by weight of active agent, 0 to 20% of agriculturally acceptable surfactants, and 10 to 99.99% of solid or liquid formulation inactive substances and adjuvants, the active agent comprising at least 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide, together with components (B) and (C), and optionally other active agents, in particular microbicides or preservatives, or the like. The compositions in concentrated form generally contain about 2 to 80% by weight of active agent, preferably about 5 to 70% by weight of active agent. The application form may contain, for example, 0.01 to 20% by weight of active agent, preferably 0.01 to 5% by weight of active agent. Commercially available products are preferably formulated as concentrates, although end users typically utilize diluted formulations.

[0040] 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide may be the only active ingredient of the composition or may be mixed with one or more additional active ingredients (e.g., insecticides, fungicides, synergists, herbicides, or plant growth regulators, as appropriate). The additional active ingredients may, in some cases, provide unexpected synergistic activity.

[0041] Examples of suitable additional active ingredients include compounds selected from the group of substances consisting of: petroleum oils, 1,1-bis(4-chloro-phenyl)-2-ethoxyethanol, 2,4-dichlorophenyl benzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenyl phenylsulfone, acetoprole, aldoxycarb, amidithione, amidothioate, amiton, amiton hydrogen oxalate, amitraz, aramit, arsenic trioxide, azobenzene, azotoate, benomyl, benoxafos, benzyl benzoate, bixafen, brofenvalerate, bromocyclen, bromophos, bromopropylate, buprofezin, butocarboxim, butoxycarboxylate. , butylpyridaben, calcium polysulfide, camfechlor, carbanolate, carbophenothione, cymiazole, chinomethionate, chlorbeneside, chlordimeform, chlordimeform hydrochloride, chlorphenitol, chlorfenson, chlorphenesulfide, chlorobenzilate, chloromebuform, chloromethiuron, chloropropylate chlorothiophos, cinerin I, cinerin II, cinerins, chlor Rosantel, Coumaphos, Crotamiton, Crotoxyphos, Kufuraneb, 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, Dinocap-4, Dinocap-6, Dinocap-7, Dinocap-8, Dinocap-9, Dinocap-10, Dinocap-11, Dinocap-12, Dinocap-13, Dinocap-14, Dinocap-15, Dinocap-16, Dinocap-17, Dinocap-18, Dinocap-19, Dinocap-20, Dinocap-21, Dinocap-22, Dinocap-23, Dinocap-24, Dinocap-25, Dinocap-26, Dinocap-27, Dinocap-28, Dinocap-29, Dinocap-30, Dinocap-31, Dinocap-32, Dinocap-33, Dinocap-34, Dinocap-35, Dinocap-36, Dinocap-37, Dinocap-38, Dinocap-39 ... Ton, dinopentone, dinosulfone, dinotervone, dioxathion, diphenylsulfone, disulfiram, DNOC, dofenapine, doramectin, endothion, eprinomectin, etheoate-methyl, etrifomuth, fenazaflor, fenbutatin oxide, fenothiocarb, fenpyrad, fenpyroximate, fenpyrazamine, fenson, fentrifanil, flubenzimine, flucycloxuron, fluenethyl, fluorbenside, FMC 1137, formetanate, formetanate hydrochloride,Formoparanate, gamma-HCH, gliodin, halfenprox, hexadecyl cyclopropanecarboxylate, isocarbophos, jasmolin I, jasmolin II, iodofenphos, lindane, malonoven, mecarbam, mesfolan, 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, nifluridide, nikkomycins, nitrilacarb, Nitrilacarb 1:1 zinc chloride complex, omethoate, oxydeprophos, oxydisulfoton, pp'-DDT, parathion, permethrin, fencapton, phosalone, phospholane, phosphamidon, polychloroterpenes, polynactins, proclonol, promacyl, propoxur, protidathion, protoate, pyrethrin I, pyrethrin II, pyrethrins, pyridaphenthion, pyrimitate, quinalphos, quinthiophos, R-1492, phosglycine, rotenone, shradan, sebufos ), selamectin, sofamid, SSI-121, sulfuram, sulfuramide, sulfotep, sulfur, diflovidazin, tau-fluvalinate, TEPP, terbam, tetradifon, tetrasal, thiafenox, thiocarboxim, thiofanox, thiometon, thioquinox, thuringiensin, triamiphos, triaratene, triazophos, trazulon, tripenophos, trinactin, vamidothion, vaniliprole, bethoxazin, Copper dioctanoate, copper sulfate, sibutrin, dichlorne, dichlorophen, endothal, tin, hydrated lime, nabam, quinoclamine, quinonamide, simazine, triphenyltin acetate, triphenyltin hydroxide, crufomate, piperazine, thiophanate, chloralose, fenthion, pyridin-4-amine, strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxalin-2-ylamino)benzenesulfonamide, 8-quinolinol sulfate, bronopol, copper hydroxide, cresol, dipyridinone, dodisin,Fenaminosulf, Formaldehyde, Hydralagafen, Kasugamycin, Kasugamycin hydrochloride hydrate, Nickel bis(dimethyldithiocarbamate), Nitrapyrin, Octilinone, Oxonic acid, Oxytetracycline, Hydroxyquinoline potassium sulfate, Probenazole, Streptomycin, Streptomycin sesquisulfate, Tecloftalam, Thiomersal, Adoxophyes orana GV, Agrobacterium radiobacter, Amblyseius spp., Anagrapha falcifera NPV, Anagras atomus, Aphelinus abdominalis, Aphidius koremani colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus Neide, Beauveria 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, 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 bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis, Verticillium lecanii lecanii), apholate, bisadil, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl apholate, molzide, penfluron, tepa, thiohempa, thiotepa, tetramine, uredepa, (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)-Icos-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)-Tetradec-9,11-dien-1-yl acetate, (9Z,12E)-Tetradec-9,12-dien-1-yl Acetate, 14-methyloctadec-1-ene, 4-methylnonan-5-ol and 4-methylnonan-5-one, alpha-multistriatin, brevicomin, codrel, codremon, querle, disparle, dodec-8-en-1-yl acetate, dodec-9-en-1-yl acetate, dodec-8,10-dien-1-yl acetate, dominicale, ethyl 4-methyloctanoate, eugenol, frontalin, grandolure, grandolure I, grandolure II, grandolure III, grandolure IV, hexalure, ipdienol, ipsenol, japonilure, lineatin, litlure, rupurure, medulure, megatomoic acid, methyleugenol, muscalure, octadeca-2,13-dien-1-yl Acetate, Octadeca-3,13-dien-1-yl acetate, Olfrular, Orictalure, Ostramon, Sigure, Soldigin, Sulcatol, Tetradec-11-en-1-yl acetate, Trimedrure, Trimedrure A, Trimedrure B, Trimedrure B2, Trimedrure C, Tranquol, 2-(Methylthio)ethanol, Butopyronoxyl, Butoxy(polypropylene glycol), Dibutyl adipate, Dibutyl phthalate, Dibutyl succinate, diethyltoluamide, dimethyl carbonate, dimethyl phthalate, ethyl hexanediol, hexanoic acid amide, methoxine-butyl, methyl neodecanamide, oxamate, picaridin, 1-dichloro-1-nitroethane, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane, 1,2-dichloropropane and 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 dimethylcarbamate, 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-isovalerilindane-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, acetione, acrylonitrile, aldrin, allosamidin, alixycarb, alpha-ecdysone, aluminum phosphide, aminocarb, anabasine, atidathione, azamethiphos, Bacillus thuringiensis delta endotoxins, barium hexafluorosilicate, barium polysulfide, varsuline, Bayer 22 / 190, Bayer22408, beta-cyfluthrin, beta-cypermethrin, bioethanomethylin, biopermethrin, bis(2-chloroethyl)ether, borax, bromfenvinphos, bromo-DDT, buphenalb, butacarb, butathiophos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, sebazine, chlorbicyclen, chlordane, chlordecone, chloroform, chloropicrin, chlorphoxim, chlorprazophos, cis-resmethrin, cismethrin, clocitrin, copper acetoarsenite, copper arsenate, copper oleate, kumitoate, cryolite, CS 708, cyanofenphos, cyanophos, cyclethrin, cythioate, d-tetramethylin, DAEP, dazomet, decarbofuran, diamidaphos, dikapton, diclofenthion, dicresyl, dicyclanil, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dirol, dimefluthrin, dimethane, dimethyrin, dimethylvinphos, dimethyllan, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzophos, dicyclophos, DSP, ecdysterone, EI 1642, EMPC, EPBP, ethaphos, ethiofencarb, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, EXD, fenchlorphos, fenetacarb, fenitrothion, fenoxacrim, fenpyritrin, fensulfothion, fenthion ethyl, flucofuron, fosmetilan, fospirate, fostietan, franthiocarb, fretrin, guazatine, guazatine acetate, sodium tetrathiocarbonate, halfenprox, HCH, HEOD, hepatachlor, heterophos, HHDN, hydrogen cyanide, hikincarb, IPSP, isazofos, isobenzan, isodrin, isofenphos, isolane, isoprothiolane, isoxathion, juvenile hormone I, juvenile hormone II, juvenile hormone III, kereban, kinoprene, lead arsenate, leptophos, rilinphos, ritidathion, m-cumenylMethyl carbamate, magnesium phosphide, magidox, mecarfone, menazone, mercuric chloride, mesulfenphos, metam, metam-potassium, metam-sodium, methanesulfonyl fluoride, methoclotophos, methoprene, methotrin, 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, PH60-38, Phenkapton, Phosnichlor, Phosphine, Phoximmethyl, Pyrimetaphos, Polychlorodicyclopentadiene isomers, Potassium arsenite, Potassium thiocyanate, Precocene I, Precocene II, Precocene III, Primidophos, Profluthrin, Promecarb, Prothiophos, Pyrazophos, Pyresmethrin, Keasia, Quinalphos-methyl, Quinothione, Lafoxanide, Resmethrin, Rotenone, Kadethrin, Riania, Ryanodine, Sabadila, Shradan, Cebuphos, SI-0009, Thiapronil, Sodium arsenite, Sodium cyanide, Sodium fluoride, Sodium hexafluorosilicate, Sodium pentachlorophenol, Sodium selenate, Sodium thiocyanate, Sulcofuron, Sulcofuron sodium, Sulfuryl fluoride, Sulprofos, Tar oils, Tazimcal , TDE, tebupirimfos, temephos, terallethrin, tetrachloroethane, triclofos, thiocyclam, thiocyclam hydrogen oxalate, thionazine, thiosultap, thiosultap sodium, tralomethrin, transpermethrin, triazamate, trichloromethaphos-3, trichloronate, trimethacarb, tolprocarb, triclopiricarb, triplen, veratridine, veratrine, XMC, zetamethrin, zinc phosphide, zolaprophos, meperfluthrin, tetramethylfluthrin, bis(tributyltin) oxide, bromoacetamide, ferric phosphate, cycloamidooxamine, 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, benclothiaz, cytokinins, DCIP, furfural, isamidophos, kinetin, Myrothecium verrucaria composition, tetrachlorothiophene, xylenols, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, Reynoutria sakarinensissachalinensis extract, alpha-chlorohydrin, antu, 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, sciriloside, sodium fluoroacetate, thallium sulfate, warfarin, 2-(2-butoxyethoxy)ethyl piperonylate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol with nerolidol, berubutin, MGK264, piperonyl butoxide, piperotal, propyl isomer, S421, sesamex, sesamolin, sulfoxide, anthraquinone, copper naphthenate, basic copper chloride, dicyclopentadiene, thiram, zinc naphthenate, ziram, imanin, ribavirin, chlorinconazide, mercuric oxide, thiophanate methyl, azaconazole, butertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, fludirazole, Lutriafol, furametpyr, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazol, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyrizoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, ancymidol, fenarimol, nuarimol, bupirimate, dimethirimol, ethirimo , dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofrace, oxadixyl, carbendazim, debacarb, fuberidazole, thiabendazole, chlozolinate, diclozolin, mycozolin, procymidone, vinclozolin, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxyl Shin, penthiopyrad, thifluzamide, dodine, iminoctadine, azoxystrobin, dimoxystrobin, enestrobulin, fenaminostrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, ferbam, mancozeb, maneb, metiram, propineb, zineb, captafol, captan, fluoroimide, folpet, Trifluanid, Bordeaux mixture, copper oxide, mancopper, oxine copper, nitrothalisopropyl, 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, felim Zon, fluazinam, flumethylsulfolim, fluopicolide, fluoxythioconazole, flusulfamide, fluxapyroxad, fenhexamid, fosetylaluminum, hymexazole, iprovalicarb, cyazofamid, methasulfocarb, metrafenone, pencycuron, phthalide, polyoxins, propamocarb, pyribencarb, proquinazid, pyroquilon, pyriophenone, quinoxyfen, quintozene, tiadinil, triazoxide, tricyclazole, triforine, validamycin, valifenalate , Zoxamide, Mandipropamide, Fluveneteram, Isopyrazam, Sedaxane, Benzovindiflupyr, Pydiflumetofen, 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, Isoflucipram, Isotianil, Dipimethitrone, 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-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-1,3-Dimethyl-1H-pyrazol-5-amine, Fluindapyr, Qumethoxystrobin (Diaxianjunchi), Lvbenmixianan, Diclobenthiazox, 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, trolprocarb, mefentrifluconazole, 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-piperidyl]thiazol-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, amethoctrazine, amisulbrom, penflufen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, flurylpicoxamide, fenpicoxamide, methallylpicoxamide, tebufloquine, ipflufenoquine, quinofumelin, isofetamide, 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, phenamacryl, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1), fluopyram, flufenoxadiazam, flutianil, fluopimomide, pyrapropoin, picarbutorazox, 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, Methyltetraprole, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide xamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol, fluoxapiproline, enoxastrobin, 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-[[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, cumoxystrobin, zhongshengmycin, copper thiadiazole, zinc thiazole, amethotractin (amectotractin), 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-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-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 were prepared from the method described in WO 2015 / 155075). N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from 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)oxetan-2-yl]phenyl]-N-methyl-formamidine fluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-foamylidene (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]-7,8-difluoro Oro-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-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 are described in WO 2017 / 153380, can be prepared from the methods described; 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)-4,4,6-trifluoro-3,3-dimethyl-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 are 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 methods 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]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]-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 methods 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-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared from 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 from the method described in WO 2016 / 156290); (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 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; (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]menthanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]menthanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds can be prepared from the methods described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (these compounds can be prepared from the methods 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 / 158365); 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]phenyl]acetamide, 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 from the methods described in WO 2018 / 202428);

[0042] The invention will now be described with reference to the following examples, which are illustrative and in no way limit the scope of the invention, which demonstrate the ability of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide (pydiflumetofen) to control or inhibit the effects of plant pathogens. EXAMPLES

[0043] Biological Examples Example 1 - Effect of pydiflumetofen on Xanthomonas perforans (tomato bacterial spot disease) The experiment was carried out in a greenhouse at the Olericulture Sector of the Federal University of Goias, where temperature and humidity are controlled. Tomato seedlings of the cultivar Totale with two true leaves were transplanted into 1 L pots containing commercial medium. Two days after transplanting, the first application of substances was carried out. Bion (acibenzolar-S-methyl, 25 g product / ha to 12.5 g ai / ha), Miravis (pydiflumetofen, 0.60 kg product / ha to 120 g ai / ha), Kocide (copper hydroxide, 1.50 kg product / ha) and Kasumin (kasugamycin, 2 L product / ha) were evaluated. An untreated control received only water. For application, the pots were placed on the bed and spraying was carried out using a spraying device (having 6 nozzles with a nozzle spacing of 0.5 m) equipped with a pressurized CO2 sprayer, with a spray volume of 300 L / ha.

[0044] Applications were performed on days 1, 7, and 14. On day 9 (between the second and third applications), inoculation with a Xanthomonas perforans isolate was performed. The plants were sprayed uniformly on all leaves with a suspension of this pathogen at a concentration of 107 colony forming units per milliliter (cfu / mL). Three assessments were performed at 6, 13, and 18 days after inoculation (DAI), and the percentage of damaged leaves (leaf area with bacterial spot) was calculated.

[0045] [Table 1]

[0046] The data in Table 1 show that pydiflumetofen provides good control of Xanthomonas perforans for up to 18 days after inoculation.

[0047] Example 2: Comparison of SDHI fungicides against Xanthomonas orycea / rice / prevention (rice bacterial spot disease) Three-week-old rice plants, cultivar Balilla, were treated with the formulated test compounds in a spray chamber. Two days after application, the rice plants were infected by cutting the upper part of the leaf and painting the bacterial suspension on the cut edge. After an incubation period of 14 days at 23° C. and 80% relative humidity, visual assessment of disease level was performed.

[0048] [Table 2]

[0049] The data in Table 2 show that pydiflumetofen provided good control of Xanthomonas orycea in the range of 20-60 mg ai / L, with marginal effectiveness at 6 mg ai / L. Other SDHI fungicides tested did not provide control or suppression of Xanthomonas orycea.

[0050] Example 3: Effect of pydiflumetofen on Xanthomonas campestris on zinnia Vegetatively mature Zinnia plants were treated with pydiflumetofen treatments via foliar spray (for Xanthomonas or Pseudomonas spp.). One to two days after treatment, the plants were sprayed with a bacterial suspension (1×108 cfu / mL, measured by spectrophotometer) and maintained at 100% relative humidity for 24 to 48 hours to promote infection. The plants were then maintained in a greenhouse or outdoor shade structure and disease incidence and severity were recorded, as well as plant health and fresh weight, if applicable.

[0051] [Table 3]

[0052] The data in Table 3 show that pydiflumetofen provides good control of Xanthomonas campestris.

[0053] Example 4. Effect of pydiflumetofen on Ralstonia spp. on geranium Vegetatively mature geranium plants were treated with pydiflumetofen treatment with a drench (Ralstonia spp.). One to two days after treatment, inoculum was applied as a soil drench. The plants were then maintained in a greenhouse or outdoor shade structure and disease incidence and severity was recorded.

[0054] [Table 4]

[0055] The data in Table 4 shows that pydiflumetofen provides control or suppression of Ralstonia spp.

Claims

1. A method for controlling or suppressing a plant pathogen on a useful plant, comprising applying an effective amount of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide to the plant, plant part, or location thereof, wherein the plant pathogen is Xanthomonas campestris or Xanthomonas perforans, and the useful plant is rapeseed, mustard, cabbage, zinnia, sunflower, lettuce, tomato, potato, bell pepper, paprika, or tobacco.

2. The method according to claim 1, comprising applying an effective amount of a composition containing 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide to the plant, plant part, or location thereof.

3. The method according to claim 1 or 2, wherein the useful plant is a tomato or a zinnia.

4. The method according to any one of claims 1 to 3, wherein 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide is applied to the plant, plant part, or location thereof in an amount of 20 g to 600 g per hectare.

5. Use of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide, or an agriculturally acceptable salt, isomer, stereoisomer, diastereoisomer, enantiomer, or tautomer thereof, wherein the plant pathogen is Xanthomonas campestris or Xanthomonas perforans, and the useful plant is rapeseed, mustard, cabbage, zinnia, sunflower, lettuce, tomato, potato, bell pepper, paprika, or tobacco.

6. The use according to claim 5, wherein the useful plant is a tomato or a zinnia.

7. The use according to claim 5 or 6, wherein 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide is applied to the plant, plant part, or location thereof in an amount of 20 g to 600 g per hectare.